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Review

Organically Templated Uranyl Sulfates and Selenates: Structural Complexity and Crystal Chemical Restrictions for Isotypic Compounds Formation

by
Elizaveta V. Durova
,
Ivan V. Kuporev
and
Vladislav V. Gurzhiy
*
Department of Crystallography, Institute of Earth Sciences, St. Petersburg State University, University Emb. 7/9, Saint-Petersburg 199034, Russia
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2023, 24(16), 13020; https://doi.org/10.3390/ijms241613020
Submission received: 31 July 2023 / Revised: 17 August 2023 / Accepted: 18 August 2023 / Published: 21 August 2023
(This article belongs to the Special Issue Recent Advances in Molecular and Hybrid Structures: Synthesis, Diagnostics, and Applications)
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Abstract

:
This paper reviews the state of the art in the structural chemistry of organically templated uranyl sulfates and selenates, which are considered as the most representative groups of U-bearing synthetic compounds. In total, there are 194 compounds known for both groups, the crystal structures of which include 84 various organic molecules. Structural studies and topological analysis clearly indicate complex crystal chemical limitations in terms of the isomorphic substitution implementation, since the existence of isotypic phases has to date been confirmed only for 24 compounds out of 194, which is slightly above 12%. The structural architecture of the entire compound depends on the combination of the organic and oxyanion parts, changes in which are sometimes realized even while maintaining the topology of the U-bearing complex. An increase in the size of the hydrocarbon part and number of charge functional groups of the organic cation leads to the formation of rare and more complex topologies. In addition, the crystal structures of two novel uranyl sulfates and one uranyl selenate, templated by isopropylammonium cations, are reported.

1. Introduction

Crystal chemical studies of uranium compounds began to develop actively in the middle of the last century; however, the most rapid growth of structural research occurred at the turn of the century and continues to this day. Of particular interest from the structural chemistry point of view is the study of hexavalent uranium compounds. The unique structural diversity cannot leave indifferent researchers in the field of crystallography, thereby generating new discovered substances and new published papers every year. Two of the most abundant groups of synthetic U-bearing compounds are uranyl selenates and sulfates, and a significant portion of them are hybrid organic–inorganic compounds. Their study is of genuine interest, since such complexes inherit the properties of both structural components: a solid inorganic uranium-bearing structure and a flexible organic one.
At present, almost 200 organically templated compounds within both named groups are known (Table 1). In this review, we evaluate the possibility of isostructural compounds’ existence among uranyl sulfates and selenates, as well as involve a recently developed analytical approach to calculating the structural complexity parameters, which allows the comparison of crystal structures in terms of the information content. In addition, we report on a description of the crystal structures of three novel uranyl compounds, [C3H10N]2[(UO2)6(SO4)7(H2O)2] (1), [C3H10N]2[(UO2)2(SO4)3(H2O)](H2O) (3), and [C3H10N](H3O)[(UO2)2(SeO4)3(H2O)](H2SeO3) (4), and on the refinement of the previously studied compound [C3H10N]2[(UO2)2(SeO4)3(H2O)](H2O) (2) to twice-better convergence parameters and interatomic bonds precision, all of which are templated by isopropylammonium cations, which are reported herein.

2. Results and Discussion

2.1. Crystal Structure Description

The crystal structure of 1 contains three crystallographically non-equivalent U6+ atoms, which are strongly bonded to two O2− atoms, forming linear (within 2.5°) O2−≡U6+≡O2− uranyl cations (Ur) with U6+≡O2− bond lengths ranging from 1.738(10) to 1.784(10) Å. The Ur1 and Ur2 ions are coordinated in the equatorial plane by five O atoms of sulfate tetrahedra, which results in the formation of UrO5 pentagonal bipyramids (U1,2–Oeq = 2.337(9)–2.449(8) Å). The Ur3 ion is coordinated by four O atoms of sulfate tetrahedra and an H2O molecule to form a Ur3O4(H2O) pentagonal bipyramid (U3–Oeq = 2.337(10)–2.539(9) Å). Four non-equivalent S6+ cations are tetrahedrally coordinated by 4 O, each with S6+–O2− bond lengths ranging from 1.437(10) to 1.482(9) Å. All sulfate tetrahedra are four-dentate bridging. Uranyl pentagonal bipyramids and sulfate tetrahedra share common edges to form a microporous framework of a [(UO2)6(SO4)7(H2O)2]2– composition (Figure 1a) with elliptical spiral channels passing along the c-axis of c.a. 7.6 × 6.8 Å in diameter, if calculated as the shortest distance between terminal O atoms, which is equal to c.a. 4.9 × 4.1 Å of a free diameter (assuming a O2− radii of 1.35 Å). One crystallographically non-equivalent isopropylammonium cation is arranged within the channel, compensating for the negative charge of the framework and forming strong (N–H···O) and weak (C–H···O) H-bonding systems with uranyl and bridging O atoms. The topology of the uranyl sulfate framework in 1 was similar to that found in isotypic uranyl sulfate compounds templated by protonated 1-butylamine [C4H10N]2[(UO2)6(SO4)7(H2O)2] (28) [11] and tetramethylammonium [C4H12N]2[(UO2)6(SO4)7(H2O)2] (74) [35] cations, as well as in a number of inorganic and organically templated uranyl molybdates [82,83,84].
The crystal structures of 2 and 3 are fully isotypic. There are two non-equivalent U6+ atoms, forming Ur with U6+≡O2− bond lengths falling in the range of 1.757(4)–1.766(3) and 1.763(2)–1.781(2) Å (for 2 and 3, respectively). The Ur1 ions are coordinated in the equatorial plane by five O atoms of selenate/sulfate tetrahedra, which results in the formation of UrO5 pentagonal bipyramids (U1–Oeq = 2.352(3)–2.438(3) and 2.340(2)–2.440(2) Å, for 2 and 3). The Ur2 ion is coordinated by four O atoms of selenate/sulfate tetrahedra and an H2O molecule to form a Ur2O4(H2O) pentagonal bipyramid (U2–Oeq = 2.343(3)–2.512(4) and 2.341(2)–2.483(2) Å, for 2 and 3, respectively). There are three non-equivalent tetrahedral sites occupied by Se6+ (2) and S6+ (3) ions that are surrounded by 4 O atoms each with T6+–O2− bond lengths falling in the range of 1.603(4)–1.653(3) and 1.441(2)–1.496(2) Å (for 2 and 3, respectively). All tetrahedral groups are three-dentate bridging. Uranyl pentagonal bipyramids and selenate/sulfate tetrahedra share common edges to form a layered complex of [(UO2)2(TO4)3(H2O)]2– (T = S, Se) composition (Figure 1b) and are arranged parallel to (001). The negative charge of the layer is compensated by two non-equivalent isopropylammonium cations that are arranged within the interlayer space along with one additional H2O molecule.
The crystal structure of 4 is very similar to 2 and 3. It is also based on the layered complexes of a [(UO2)2(SeO4)3(H2O)]2– composition with the following bond-length ranges: U≡OUr = 1.759(4)–1.767(3) Å; U1–Oeq = 2.374(3)–2.443(3) Å; U2–Oeq = 2.359(3)–2.480(4) Å; and Se6+–O = 1.612(4)–1.658(3) Å. The difference between structures 2 and 4 lies in the interlayer space. If there are two isopropylammonium cations and one H2O molecule in the structure of 2, the structure of 4 contains one isopropylammonium cation, one hydronium ion, and an additional selenous acid molecule [H2SeO3]0 with Se4+–O = 1.681(4)–1.732(5) Å. It is also of interest that quite unusual interatomic interactions are observed in the structure of 4 between the Se4(IV) atom of the [H2SeO3]0 molecule and O2 of the Ur2 ion (Se4···O6 = 3.000(4) Å and O20–Se4···O2 = 172.2(2)°), terminal non-shared O17 atom of the [Se1O4]2– selenate tetrahedra (Se4···O17 = 3.112(4) Å and O19–Se4···O17 = 140.4(2)°), O13 of the Ur1 ion (Se4···O13 = 3.359(4) Å and O19–Se4···O13 = 148.1(2) °); however, the closest contact is observed between Se4 and O6 of the Ur1 ion (Se4···O6 = 2.730(4) Å and O21–Se4···O6 = 176.8(2)°). All these interatomic distances, especially the latter, are lower than the sum of the Se and O van der Waals radii (1.9 + 1.55 = 3.45 Å [85]); therefore, they can be attributed to chalcogen bonding [86,87,88,89].

2.2. Structural Topology

The layered complexes in the structures of 2–4 belong to one of the most common topological types (cc2–2:3–4) among uranyl compounds of both pure inorganic or organically templated origin. The topology of the layer can be represented by a black-and-white graph where Ur polyhedra are denoted by black vertices, SO4 or SeO4 coordination polyhedra are denoted by white vertices, and two vertices are connected by a line if the corresponding polyhedra have a common O atom (Figure 1c). Within the current review, the structures of 24 organically templated uranyl sulfates and selenates are based on the layers of this topology, including compounds 2–4. Being tridentate bridging, sulfate and selenate tetrahedra have their fourth non-shared O atom arranged up or down relative to the plane of the layer. This variability can generate the formation of geometrical isomers with various orientations of tetrahedral groups that can be described by the orientation matrices [90]. Symbols u (up), d (down), or □ (tetrahedra missing in the graph) are assigned to each tetrahedral site (white vertex) at the graph of the layer (Figure 1c). The aforementioned change in the interlayer space filling results, however, does not entail differences in the geometric isomerism of the layers. Thus, the orientation matrix for the U-bearing layers in the structures of 2–4 can be written as (uud□)/(□udd). Moreover, the degree of layer distortion is also the same. Layer undulation (Figure 2a,b) can be calculated as the shortest interatomic distance between the neighbor wave crests, and the thickness can be calculated as the normal distance between the mean planes that pass through the most protruding parts of the layer (i.e., terminal O atoms of the tetrahedra). The layer undulation and thickness parameters are 7.5 and 5.9 Å, 7.2 and 5.6 Å, 7.4 and 5.9 Å for 2–4, respectively. The substitution of the isopropylammonium cation and H2O molecule by a selenous acid molecule and H3O ion results in the orthogonalization of the unit cell of 4, and in the alignment of neighboring layers.
It is known that hydrophilic amine groups of organic cations in the structures of organically templated uranyl compounds prefer to associate with dense fragments of U-bearing substructural complexes (four-membered rings of the graph), while hydrocarbon components of the molecules, which do not play a charge-compensating role, are usually arranged in front of rarefied zones (six-membered rings of the graph). It is of interest that the arrangement of the isopropylammonium cation in the structure of 4 fully corresponds to that in the structures of 2 and 3 (Figure 2c,d). The arrangement of the selenous acid molecule in 4 plays a role of the hydrocarbon part of the second isopropylammonium cation in 2 and 3, so that the H3O+ molecule occupies a position different from H2O in the structures of 2 and 3, and functions as an amino group.

3. Discussion

3.1. Isotypic Uranyl Sulfates and Selenates

An aforementioned example demonstrates the rather high resistance of the U-bearing structural type to substitutions in the oxyanion substructural complex. However, this case in the total amount of known structural data is not so frequent. Only 11 pairs of isotypic sulfate–selenate compounds, excluding those reported here, are known. Most of them account for the uranyl compounds templated by various amino acid molecules (174–185, 188, 189 [76]). Two pairs correspond to quite rare piperazine (122 [47], 123 [48]) and 3-Aminotropane (154, 155 [64]) molecules. Additionally, only two pairs of compounds represent more common organic molecules that were used in the synthetic experiments: 1-butylamine (26 [11], 30 [14]) and tetramethylammonium (71 [33], 72 [34]). There are also several examples of a very close structural architecture, for example, compounds templated by 1,4-diaminobutane (47 [12,13], 48 [26]) and N.N-dimethylethylenediamine (89 [43], 91 [36]). Those pairs of compounds have the same topology of the U-bearing layers, and even close unit cell parameters; however, an arrangement of the respective organic and additional H2O molecules in the interlayer space differs, which leads to the impossibility of classifying them as isotypic compounds.

3.2. Topology of U-Bearing Complexes

An analysis of Table 1 demonstrates the following distribution of U-bearing substructural complexes. There are four compounds, of which the structures contain isolated uranyl sulfate or selenate moieties, which possess three different topologies. The crystal structures of 49 compounds are based on the 1D U-bearing chains of 9 various topological types, among which two topologies cc1–1:2–12 (13 compounds with [UO2(TO4)2]2– or [UO2(TO4)(NO3)]− (T = S, Se) composition) and cc1–1:2–1 (17 compounds with [UO2(TO4)2 H2O] (T = S, Se) composition) account for more than half of all the considered chain-based crystal structures (Figure 3a-e). Compound 96 [42] should be especially mentioned, since it is the only compound within those under consideration, of which the crystal structure is based on units of different topological types (cc1–1:1–2 and cc1–1:2–8). The vast majority of organically templated uranyl sulfates and selenates (135 compounds) have their structures based on layered U-bearing complexes, which is fully consistent with the general trend for U(VI) compounds [48,91,92,93]. Among them, three topologies that prevail over others can be quite clearly distinguished as well. Those are cc2–1:2–2 (16 compounds with [(UO2)(TO4)2(H2O)]2– (T = S, Se) composition), cc2–2:3–10 (17 compounds with [(UO2)2(TO4)3(H2O)]2– (T = S, Se) composition), and cc2–2:3–4 (22 compounds with [(UO2)2(TO4)3(H2O)]2– (T = S, Se) composition) (Figure 3f-k). Moreover, the cc2–2:3–10 topology of the layered U-bearing complexes was observed in the structures of the compounds templated by 11 various organic molecules; the cc2–1:2–2 topology was described for 11 molecules of various shapes and sizes, and the most common topological type, cc2–2:3–4, was observed in the structures with 17 various amine molecules. There were five compounds, including compound 1, of which the structures were based on microporous frameworks. Additionally, the crystal structures of 31, 166, and 191 contained nanotubules, formed by vertex-sharing of Ur bipyramids and sulfate or selenate tetrahedra. It is of interest that nanotubules in all three compounds can be unfolded into the planar fragments of the cc2–3:5–2 topological type.

3.3. Structural Complexity

The method of calculating and analyzing structural complexity parameters has been quite successfully used in the study of mineral associations [94,95,96,97], as well as in the analysis of various groups of inorganic compounds, including uranyl compounds [98,99,100,101].
Considering the full set of available structural data, the only obvious correlation was observed between complexities of the U-bearing structural unit and entire structure (Figure 4a).
On the one hand, this trend is rather obvious: the more complex the structural unit, the more complex the structure is. However, one should keep in mind that the most accurate comparison and analysis of the calculated complexity values are possible for compounds with similar chemical compositions (polymorph modifications). Deviations in the chemical composition or, to be more precise, in a number of atoms in the crystal structure automatically create certain allowances, since the complexity parameters directly depend on the number and multiplicity of atomic sites. For example, a single H2O molecule introduces three atomic sites into the calculation. Therefore, organic molecules should contribute to the overall complexity due to the large number of atomic sites compared to the inorganic substructural unit. However, there is no such tendency observed in the graphs, if complexity values per unit cell are taken into account (Figure 4b,c). The situation becomes somewhat better when using complexity parameters per atom (Figure 4d,e). However, even here, there were no real trends, minor tendencies. This was mainly due to the fact that organic molecules with similar numbers of atoms had completely different functionalities (size, shape, number of amino groups, etc.), which presented different effects on the U-bearing structural complexes. Therefore, it made sense to consider some groups of molecules separately.
Thus, the most representative groups were the rows of chained amine and diamine molecules. For these groups, firstly, there was a long-term trend towards an increase in the hydrocarbon part of the molecule, and secondly, there were relatively large numbers of representatives to obtain better statistics. Both of these statements are more relevant to the group of diamines; however, in comparison with the other types of molecules, the statistics are, unfortunately, less obvious. As it can be seen from the graph (Figure 5), an increase in the length of the hydrocarbon moiety of the chain amine correlates both with an increase in the complexity of the entire structure (which is expected) and with an increase in the complexity of the uranyl-bearing substructural complex. Of course, the trend line cannot be called absolute, but rather a trend of the average complexity values for each of the molecules.
A rather good agreement with this tendency can also be observed for compounds with amino acid molecules (Figure 6).
Most of the remaining groups of molecules did not have a large number of compounds available; therefore, it was rather difficult to analyze them. However, several interesting trends could be observed as well. Considering the features of cyclic molecules, one can notice that small strained molecules, such as azetidine, pyridine, imidazole, etc., are located at the beginning of the graph (Figure 7a,b). Those points correspond to rather complex U-bearing structural units, as well as structures in general. As the cycle increases and multiple bonds disappear, the complexity of the substructural building units decrease. Additionally, they begin to increase again as branches from the cyclic base appear.
The importance of the number of atoms is well illustrated in the calculation of complexity parameters by the example of crown molecules (Figure 7c,d). Crown ether molecules do not contain amino groups and are electrically neutral within the structures of the corresponding compounds. Thus, the role of their size in the formation of more complex structures is not clearly traced. This is all the more obvious if one compares the molecules of 12-crown-4 ether and cyclene, which are nearly identical in size and shape. The presence of four amino groups in the structure of the latter, instead of four O atoms, firstly affects the complexity of the molecule itself (eight additional atoms), and secondly increases the complexity of substructural units due to the active participation of amino groups in a particular topology templating process.

4. Materials and Methods

4.1. Synthesis

Caution: While isotopically depleted U was used in these experiments, precautions for handling radioactive materials should be followed.
Uranyl nitrate hexahydrate ((UO2)(NO3)2∙6H2O, Vekton, 99%), uranyl acetate ((UO2)(CH3COO)2·2H2O, Vekton, 99%), sulfuric acid (H2SO4, Aldrich, 98%), selenic acid (H2SeO4, 40 wt. % in H2O, Aldrich, 99.95%), 1-butylamine (C4H11N, Aldrich, ≥99.5%), and isopropylamine (C3H9N, Aldrich, ≥99.5%) were used as received.
To reveal the features of the isotypic uranyl compounds’ crystallization upon substitution in cationic and anionic substructural complexes, a series of synthetic experiments were conducted. Uranyl sulfate with a microporous structure [C4H12N]2[(UO2)6(SO4)7(H2O)2] (28) [11], in the channels of which small-chained molecules of 1-butylamine were arranged, was chosen as the starting point. A similar ratio of initial reagents was taken; however, another small amine with a branched aliphatic part, isopropylamine, was chosen as an organic template.
An aqueous solution of 0.1720 g (0.34 mmol) of uranyl nitrate was dissolved in 4 mL of deionized distilled water. Then, 0.500 mL (9.38 mmol) of H2SO4 and 0.012 mL (0.14 mmol) of isopropylamine were added to the solution, which was stirred until all solid material dissolved. The resulting yellowish transparent solution was left to evaporate in a watch glass at room temperature. Individual, single, flat, rhombic crystals of 1 (Figure 8a) began crystallizing after 3 days. It should be noted that compound 1 was also obtained using another protocol as follows. An aqueous solution of 0.6400 g (1.51 mmol) of uranyl acetate was dissolved in 1 mL of deionized distilled water. Then, 0.200 mL (3.75 mmol) of H2SO4 (98%) and 0.012 mL (0.14 mmol) of isopropylamine were added to the solution, which was stirred until all solid material dissolved. The resulting yellowish transparent solution was placed in a steel autoclave with a Teflon capsule, which was kept in an oven at a temperature of 180 °C for 24 h. After cooling, the solution was poured onto a watch glass, where individual crystals of 1 began crystallizing after 30 min.
An attempt to crystalize the selenate compound isotypic to 1 was unsuccessful. An analysis of the crystalline precipitate showed that a [C3H10N]2[(UO2)2(SeO4)3(H2O)](H2O) (2) phase was formed, which was previously reported in [12,13]. To avoid the accidental crystallization of the compound 2, several experiments were performed in an extended range of initial reagent concentrations with approximately the same molar ratios. The best-quality single crystals of 2 were formed under the following conditions. An aqueous solution of 0.0880 g (0.18 mmol) of uranyl nitrate was dissolved in 2 mL of deionized distilled water. Then, 0.220 mL (1.79 mmol) of H2SeO4 (40%) and 0.006 mL (0.07 mmol) of isopropylamine were added to the solution, which was stirred until all solid material dissolved. The resulting yellowish transparent solution was left to evaporate in a watch glass at room temperature. The formation of crystals started in 2 days (Figure 8b). Although the crystal structure of 2 was previously described [12,13], we reported here on the refinement of its structural model with better precision.
To obtain a sulfate compound isotypic to 2, the following experiment was conducted. An aqueous solution of 0.0880 g (0.18 mmol) of uranyl nitrate was dissolved in 2 mL of deionized distilled water. Then, 0.103 mL (1.92 mmol) of H2SO4 (98%) and 0.006 mL (0.07 mmol) of isopropylamine were added to the solution, which was stirred until all solid material dissolved. The resulting yellowish transparent solution was left to evaporate in a watch glass at room temperature. The formation of individual, flat, octagonal crystals of 3 started in 3 days (Figure 8c).
The final attempt to substitute isopropylamine in the synthetic protocol of 2 with 1-butylamine molecules was unsuccessful and resulted in the formation of a [C4H12N][H3O][(UO2)2(SeO4)3(H2O)] (29) compound, where the structure was based on the layered complexes with another topology [12,13].
It is of interest that, for the synthesis of 2, a newly obtained selenic acid was used, while compound 4 was synthesized using a selenic acid reagent stored for ~2 years (Figure 8d). This resulted in the incorporation of electroneutral H2SeO3 molecules in the interlayer space of 4 (see Chapter 2 for details). The Se(VI) reduction to the 4+ oxidation state during the long-term storage of the selenic acid reagent is a rather frequent process, which was repeatedly noted previously [27,30,100].

4.2. Chemical Analysis

The chemical analyses of small pieces of individual single crystals of 1–4, preliminary checked using a single-crystal X-ray diffractometer, were performed using a Hitachi TM 3000 scanning electron microscope equipped with an Oxford EDX spectrometer, with an acquisition time of 30 s per point in an energy dispersive mode (acceleration voltage: 15 kV). The following standards and X-ray lines were used: S—pyrite (FeS2), Kα; Se—PbSe, Kα; and U—U3O8, Mβ.
Analytical calculations. Compound 1, atomic ratio from structural data: U 6.0, S 7.0; found by EDX: U 5.94, S 7.06. Compound 2, structural data: U 2.0, Se 3.0; found by EDX: U 1.92, Se 3.08. Compound 3, structural data: U 2.0, S 3.0; found by EDX: U 2.02, S 2.98. Compound 4, structural data: U 2.0, Se 4.0; found by EDX: U 2.11, S 3.89.

4.3. Single-Crystal X-ray Diffraction

Single crystals of 1–4 were selected under an optical microscope in polarized light, immersed in an oil-based cryoprotectant, and fixed on cryoloops. Diffraction data were collected at 100 K using a Rigaku XtaLAB Synergy S X-ray diffractometer operated with a monochromated microfocus MoKα PhotonJet-S (λ = 0.71073 Å) source at 50 kV and 1.0 mA, and equipped with a CCD HyPix 6000HE hybrid photon-counting detector [102]. The frame width was 0.5 or 1.0° in ω, and there was a 1 to 16 s count time for each frame. Diffraction data were integrated and corrected for polarization, background, and Lorentz effects using the CrysAlisPro program [103]. An empirical absorption correction was applied based on the spherical harmonics (SCALE3 ABSPACK algorithm). The unit-cell parameters (Table 2) were refined using least-squares techniques. The structures were solved by a dual-space algorithm and refined using SHELX programs [104,105] incorporated in the OLEX2 program package [106]. The final models included coordinates and anisotropic displacement parameters for all non-H atoms. The carbon-, nitrogen- and oxygen-bound H atoms were placed in calculated positions and were included in the refinement in the ‘riding’ model approximation, with Uiso(H) set to 1.5Ueq(C) and C–H 0.98 Å for CH3 groups, Uiso(H) set to 1.2Ueq(C) and C–H 1.00 Å for tertiary CH groups, Uiso(H) set to 1.2Ueq(N) and N–H 0.91 Å for NH3 groups, Uiso(H) set to 1.5Ueq(O) and O–H 0.84 Å for OH− groups, and Uiso(H) set to 1.5Ueq(O) and O–H 0.87 Å for H2O molecules. Supplementary crystallographic data for 1–4 can be downloaded from the Supplementary Materials section and from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures/.

4.4. Structural Complexity Calculations

A structural complexity approach was recently developed by S.V. Krivovichev [107,108,109,110,111,112]. This method allows estimating the information content of each particular crystal structure, as well as its substructural components. It appears to be quite useful for comparing isotypic or similar structures and quantitatively characterizing the contribution of each substructural component (uranyl sulfate or selenate complexes, interstitial organic template, etc.) to the formation of the whole structural architecture of the compound. The approach is based on the Shannon information content calculations of per atom (IG) and per unit cell (IG,total) using the following equations:
I G = − ∑ i = 1 k p i   log 2   p i     ( bits/atom )
I G,total = − v   I G = − v ∑ i = 1 k p i   log 2   p i   ( bits/cell )
where k is the number of different crystallographic orbits (independent sites) in the structure and pi is the random choice probability for an atom from the i-th crystallographic orbit, that is:
pi = mi/v
where mi is the multiplicity of the crystallographic orbit (i.e., the number of atoms of a specific Wyckoff site in the reduced unit cell) and v is the total number of atoms in the reduced unit cell.
It should be noted that all calculations for already-studied crystal structures were based on the original cif files, which were obtained from structural databases (CCDC and ICSD) and respective publications. In addition, if H-atom sites were not reported in the original entries, they were assigned manually considering the distribution of the H-bonding system. Complexity parameters for the organic molecules and U-bearing substructural complexes were calculated manually, while the parameters for the whole structure were determined using ToposPro software [113].

5. Conclusions

In this paper, we reviewed the state of the art in the structural chemistry of organically templated uranyl sulfates and selenates, which were considered as the most representative groups of U-bearing synthetic compounds. In total, there were 194 compounds known for both groups, including three novel ones reported here, the crystal structures of which contained 84 various organic molecules. Such statistics illustrates both the great work already performed in the field of syntheses and structural studies, but also the obvious insufficiency of specific system studies, since it turned out that, on average, there were slightly more than two compounds per molecule. Nevertheless, quite clear regularities could be formulated for a number of groups of compounds. Thus, in accordance with the analysis, an increase in the size of the hydrocarbon part and number of charge functional groups of the organic cation led to the formation of rare and more complex topologies.
The presence, albeit in a small number, of isostructural compounds for complex molecules and the absence of such compounds for simpler ones indicated a very fine interaction between the inorganic oxyanion and organic positively charged parts of the structures. Large molecules, apparently, created a kind of a buffer due to their size and the distribution of charge-carrying amino groups, which made it possible to level the difference in the sizes of the sulfate and selenate tetrahedra. However, even in the given examples, the difficulties in obtaining isostructural sulfates and uranyl selenates were very well observed. Thus, compounds 175, 177, 179, and 189 [76] were designated as isostructural, only by the similarity of unit cell parameters, since the quality of the obtained crystals (and all of them were selenates) did not allow one to solve their structures directly. The problem of the presence of a correlation between the uranyl-bearing structural complex topology and the size and shape of the amine molecule has already been raised [12,13,14,64], and it is obvious, at present, that the structural architecture of the entire compound depends on the combination of the organic and oxyanion parts. For example, the most common layer topologies cc2–2:3–10, cc2–1:2–2, and cc2–2:3–4 (see Ch. 3.2) were described in the structures templated by amine molecules of various sizes and shapes (chained, cyclic, etc.); however, the arrangement preserved a certain position of the amino- or other charge-carrying groups. At the same time, changes in the oxyanion substructure can be sometimes realized with symmetry breaking, whilst maintaining the topology of the complex (e.g., 147, 148 [36]).
This review demonstrated the ability to form isotypic compounds, which, by analogy with recently performed studies in purely inorganic uranyl systems [98,114,115], indicated the probability of the isomorphic sulfate–selenate series’ existence with substitutions in both cationic and oxyanionic moieties. At the same time, the results of the structural studies and topological analysis of all known compounds within the groups under consideration clearly indicate complex crystal chemical limitations in terms of the isomorphic substitution implementation, since the existence of isotypic phases has to date been confirmed only for 24 compounds out of 194, which is slightly above 12%.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/ijms241613020/s1.

Author Contributions

Conceptualization, V.V.G.; Methodology, E.V.D., I.V.K. and V.V.G.; Investigation, E.V.D., I.V.K. and V.V.G.; Writing—Original Draft Preparation, E.V.D., I.V.K. and V.V.G.; Writing—Review and Editing, E.V.D., I.V.K. and V.V.G.; Visualization, E.V.D., I.V.K. and V.V.G. All authors have read and agreed to the published version of the manuscript.

Funding

This work is supported by the Russian Science Foundation (project No. 19-17-00038).

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Acknowledgments

The laboratory research was conducted out using equipment from the following resource centers of the Research Park of the Saint Petersburg State University: the X-ray Diffraction Centre and Center for Microscopy and Microanalysis.

Conflicts of Interest

The authors declare no conflict of interest.

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Ijms 24 13020 g001
Figure 1. The crystal structure of 1: (a) polyhedral representation of layers in the structures of 2–4 (b), and topology of its interpolyhedral linkage (c). Legend: U polyhedra = yellow, TO4 (T = S, Se) tetrahedra = orange; O atoms = red, N atoms = blue, C atoms = white, H atoms = gray; black nodes = U atoms, white nodes = T atoms.
Figure 1. The crystal structure of 1: (a) polyhedral representation of layers in the structures of 2–4 (b), and topology of its interpolyhedral linkage (c). Legend: U polyhedra = yellow, TO4 (T = S, Se) tetrahedra = orange; O atoms = red, N atoms = blue, C atoms = white, H atoms = gray; black nodes = U atoms, white nodes = T atoms.
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Ijms 24 13020 g002
Figure 2. The crystal structures of 2 (a) and 4 (b): location of the interlayer species in the structures of 2 (c) and 4 (d) relative to the black-and-white graph of the inorganic layer. Legend: see Figure 1.
Figure 2. The crystal structures of 2 (a) and 4 (b): location of the interlayer species in the structures of 2 (c) and 4 (d) relative to the black-and-white graph of the inorganic layer. Legend: see Figure 1.
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Ijms 24 13020 g003
Figure 3. The most common topologies of the U-bearing substructural units among organically templated uranyl sulfate and selenate compounds: chains of cc1–1:2–1 (a) and cc1–1:2–12 (c,d) types and their black-and-white graphs ((b,e), respectively); layers of cc2–1:2–2 (f), cc2–2:3–10 (h), and cc2–2:3–4 (j) topologies and their respective graphs (g,i,k). Legend: see Figure 1; blue triangles = NO3 groups; gray nodes and double line = edge-shared TO4 tetrahedra or NO3 group.
Figure 3. The most common topologies of the U-bearing substructural units among organically templated uranyl sulfate and selenate compounds: chains of cc1–1:2–1 (a) and cc1–1:2–12 (c,d) types and their black-and-white graphs ((b,e), respectively); layers of cc2–1:2–2 (f), cc2–2:3–10 (h), and cc2–2:3–4 (j) topologies and their respective graphs (g,i,k). Legend: see Figure 1; blue triangles = NO3 groups; gray nodes and double line = edge-shared TO4 tetrahedra or NO3 group.
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Ijms 24 13020 g004
Figure 4. Correlation graphs of structural complexity parameters: complexity of U-bearing structural unit vs. complexity of the entire structure (a); complexity of organic molecule vs. complexity of U-bearing structural unit and of the entire structure per unit cell (b,c) and per atom (d,e).
Figure 4. Correlation graphs of structural complexity parameters: complexity of U-bearing structural unit vs. complexity of the entire structure (a); complexity of organic molecule vs. complexity of U-bearing structural unit and of the entire structure per unit cell (b,c) and per atom (d,e).
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Ijms 24 13020 g005
Figure 5. Correlation graphs of chained amine (a,b) and diamine molecule (c,d) complexity vs. complexity of U-bearing structural unit (a,c) and of the entire structure (b,d), per atom.
Figure 5. Correlation graphs of chained amine (a,b) and diamine molecule (c,d) complexity vs. complexity of U-bearing structural unit (a,c) and of the entire structure (b,d), per atom.
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Ijms 24 13020 g006
Figure 6. Correlation graphs of amino acid molecule complexity vs. complexity of U-bearing structural unit (a) and of the entire structure (b), per atom.
Figure 6. Correlation graphs of amino acid molecule complexity vs. complexity of U-bearing structural unit (a) and of the entire structure (b), per atom.
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Ijms 24 13020 g007
Figure 7. Correlation graphs of cyclic organic molecule complexity vs. complexity of U-bearing structural unit (a,c) and of the entire structure (b,d), per atom.
Figure 7. Correlation graphs of cyclic organic molecule complexity vs. complexity of U-bearing structural unit (a,c) and of the entire structure (b,d), per atom.
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Ijms 24 13020 g008
Figure 8. Crystals of 1–4 (a–d, respectively) formed in the described synthetic experiments.
Figure 8. Crystals of 1–4 (a–d, respectively) formed in the described synthetic experiments.
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Table 1. Crystallographic characteristics and structural complexity parameters of organically templated synthetic uranyl sulfates and selenates.
Table 1. Crystallographic characteristics and structural complexity parameters of organically templated synthetic uranyl sulfates and selenates.
No.Chemical FormulaeTopologySp. Gr.a, Å/α, °b, Å/β, °c, Å/γ, °Structural Complexity Parameters, Bits per Atom/Bits per Unit CellRef.
Organic MoleculeU-Bearing UnitEntire Structure
Ammonium, NH4+ Ijms 24 13020 i0012.322/11.610
5[NH4][(UO2)(SO4)F] cc2–1:1–7Pb21a8.681(3)/9011.319(8)/906.729(6)/90 3.170/114.1173.585/172.078[1]
6[NH4]2[UO2(SO4)2(H2O)](H2O) cc2–1:2–2P21/c7.783(5)/907.403(2)/102.25(4)20.918(9)/90 4.250/322.8404.858/563.526[2]
7[NH4]4[(UO2)2(SO4)O2)2](H2O) 524332C2/m8.6987(15)/9014.166(2)/104.117(4)17.847(3)/90 4.150/281.9504.956/564.949[3]
8[NH4]2[(UO2)2(SO4)O2)] 524332Cmca14.2520(9)/908.7748(5)/9017.1863(10)/90 2.780/144.4203.654/336.168[3]
9[NH4]2[(UO2)(SeO4)2(H2O)](H2O)2 cc2–1:2–3P2121218.2036(9)/9011.631(2)/9014.028(2)/90 4.000/256.0005.000/640.000[4]
Methylamine, CH3NH3+ Ijms 24 13020 i0023.000/24.000
10[CH6N]2[(UO2)2(SO4)3] cc2–2:3–14P18.4784(6)/90.170(2)9.7873(8)/95.744(2)9.8121(7)/90.136(2) 5.390/226.4806.209/459.500[5]
11[CH6N][(UO2)(SO4)(OH)] 61524232Pbca11.5951(8)/909.2848(6)/9014.5565(9)/90 3.320/265.7504.170/600.469[6]
12[CH6N]2[(UO2)(SeO4)2 (H2O)](H2O) cc1–1:2–1Pnma7.5496(7)/9012.0135(9)/9015.8362(13)/90 3.250/208.0004.272/598.100[7]
13[CH6N]2[(UO2)(SeO4)2 (H2O)] cc2–1:2–3P21/c8.2366(10) /907.5888(6)/104.566(9)22.260(2)/90 4.000/256.0005.000/640.000[7]
14[CH6N][H3O][(UO2)2 (SeO4)3(H2O)](H2O) cc2–2:3–12P21/c8.4842(10)/9010.2368(8)/102.803(9)24.228(2)/90 4.590/440.1605.285/824.523[7]
15[CH6N]2[(UO2)2(SeO4)3] cc2–2:3–14P218.5827(13)/9010.0730(15)/95.980(12)10.0915(14)/90 4.390/184.4805.209/385.500[7]
16[CH6N]4[(UO2)3(SeO4)5](H2O)4 cc2–3:5–2Pnma16.4221(14)/9018.4773(9)/9010.3602(5)/90 4.230/608.4705.311/1657.045[7]
17[CH6N][H5O2][H3O]2(UO2)3(SeO4)5] (H2O)4 cc2–3:5–2Ibca20.956(2)/9034.767(8)/9018.663(2)/90 5.170/1488.9406.150/3493.056[7]
18[CH6N]2[H3O]2[(UO2)5 (SeO4)8(H2O)](H2O)4cc2–5:8–2Pca2131.505(2)/9010.3688(6)/9016.2424(11)/90 5.860/1359.0506.807/3049.695[7]
19[CH6N]1.5[H5O2]1.5[H3O]3 [(UO2)5(SeO4)8(H2O)] (H2SeO4)2.6(H2O)3 cc2–5:8–3Pnma30.9728(19)/9037.022(2)/9010.4171(5)/90 5.880/2776.6106.749/5614.766[7]
Ethylamine, C2H5NH3+ Ijms 24 13020 i0033.459/38.054
20[C2H8N][(UO2)Cl(SO4)(H2O)] cc2–1:1–1P21/c8.3545(17)/9010.550(2)/102.64(3)12.370(3)/90 3.585/172.0784.524/416.168[8]
21[C2H8N]2[(UO2)(SeO4)2(H2O)](H2O)2cc1–1:2–1Pnma7.6176(9)/9012.1811(16)/9019.258(2)/90 3.250/208.0004.724/944.771[9]
22[C2H8N][H3O][(UO2)(SeO4)2(H2O)] cc1–1:2–1P17.5635(15)/79.559(15)7.6188(15)/89.272(16)12.101(2)/82.356(16) 4.000/128.0004.954/307.160[9]
23[C2H8N]3[(UO2)(SeO4)2(HSeO4)] cc1–1:3–2P21/c12.7463(11)/9012.4261(7)/113.433(6)14.9928(11)/90 4.248/322.8425.700/1185.691[9]
24[C2H8N][(UO2)(SeO4)(SeO2OH)] cc2–1:2–4P21/n8.475(3)/9012.264(2)/95.23(3)10.404(3)/90 3.700/192.4234.954/614.320[9]
25[C2H8N]2[(UO2)2(SeO4)3(H2O)] cc2–2:3–10P218.2897(14)/9012.349(2)/104.439(4)11.0379(18)/90 4.585/220.0785.524/508.168[10]
1-butylamine, C4H7NH3+ Ijms 24 13020 i0043.907/58.603
26[C4H10N]3[(UO2)2(SO4)3(OH)] (H2O)2 cc2–2:3–10P218.439(5)/9011.912(7)/102.79(10)10.636(6)/90 4.459/196.2155.426/466.659[11]
27[C4H10N]8[(UO2)5(SO4)9](H2O) frameworkP2121219.4586(8)/9026.769(2)/9032.377(3)/90 5.907/1417.6547.500/5429.888[11]
28[C4H10N]2[(UO2)6(SO4)7(H2O)2] frameworkC222110.2776(12)/9018.339(2)/9022.788(3)/90 4.800/527.9505.421/921.596[11]
29[C4H12N][H3O][(UO2)2(SeO4)3(H2O)] cc2–2:3–10P21/c10.7691(9)/9012.5019(12)/98.172(7)15.4620(14)/90 4.585/440.1565.492/988.534[12,13]
30[C4H12N][H5O2][(UO2)2(SeO4)3(H2O)] cc2–2:3–10P218.3908(11)/9012.3602(11)/101.567(10)10.9150(13)/90 4.459/196.2155.358/439.319[14]
31[C4H12N]14[(UO2)10(SeO4)17(H2O)] cc2–3:5–2
nanotubules		I2mm10.8864(5)/9029.532(2)/9047.439(2)/90 5.999/1403.6657.547/5268.064[15]
N-methylbutylamine, C5H12NH2+ Ijms 24 13020 i0054.322/86.439
32[C5H14N]4[(UO2)3(SeO4)4 (HSeO3)(H2O)](H2SeO3)(HSeO4) cc2–3:5–3 P 1 ¯ 11.7068(9)/73.899(6)14.8165(12)/76.221(7)16.9766(15)/89.861(6) 5.209/385.5007.011/1808.897[16]
33[C5H14N]2[H3O][(UO2)3(SeO4)4(HSeO4) (H2O)] cc2–3:5–3C2/c16.7572(13)/9011.7239(12)/98.875(6)19.0490(13)/90 4.215/295.0505.306/817.085[17]
34[C5H14N]2[H3O][(UO2)3 (SeO4)4(HSeO4)(H2O)](H2O) cc2–3:5–3P21/n10.8252(10)/9019.0007(10)/100.324(7)18.6463(15)/90 5.129/718.1006.267/1930.170[17]
Pentylamine, C5H11NH3+ Ijms 24 13020 i0064.322/86.439
35[C5H14N][(UO2)(SeO4)(SeO2OH)] cc2–1:2–4P21/n11.553(2)/9010.6445(16)/108.045(15)12.138(2)/90 3.700/192.4235.044/665.860[18]
Octylamine, C8H17NH3+ Ijms 24 13020 i0074.858/140.881
36[C8H20N]2[(UO2)(SeO4)2 (H2O)](H2O) cc2–1:2–2 P 1 ¯ 7.498(3)/89.69(3)11.897(4)/90.05(4)32.056(14)/88.80(3) 5.000/320.0007.267/2238.170[19]
Ethylenediamine, C2H4(NH3)22+ Ijms 24 13020 i0083.807/53.303
37[C2H10N2][(UO2)(SeO4)2 (H2O)](H2O) cc2–1:2–2C2/c11.787(2)/907.7007(10)/102.016(14)16.600(3)/90 3.125/100.0004.225/304.235[20]
38[C2H10N2][(UO2)(SeO4)2 (H2O)](H2O)2 cc2–1:2–2P21/c11.677(2)/907.908(1)/98.813(3)15.698(2)/90 4.000/256.0005.170/744.469[10]
39[C2H10N2][(UO2)(SeO3) (HSeO3)](NO3)(H2O)0.5 cc2–1:2–4Pbca13.170(3) /9011.055(2)/9018.009(4)/90 3.585/344.1564.954/1228.641[21]
40[C2H4(NH3)2][UO2(SO4)2H2O]cc1–1:2–1C2/c15.6163(4)/907.3018(2)/118.731(2)11.7114(3)/90 3.125/100.0003.974/238.413[22]
1.3-diaminopropane, C3H6(NH3)22+ Ijms 24 13020 i0094.087/69.487
41[C3H12N2][UO2(H2O)(SO4)2] cc1–1:2–1P2/c7.2582(2)/907.3697(2)/99.4053(19)11.8514(3)/90 3.125/100.0004.135/272.930[23]
42[C3H12N2][(UO2)2(H2O)(SO4)3] cc2–2:3–4P21/n10.7391(3)/9010.3791(3)/106.942(1)18.0265(7)/90 4.585/440.1565.358/878.639[23]
43[N2C3H12][UO2F(SO4)]2(H2O)cc2–1:1–10P216.7745(2)/908.1589(2)/94.556(1)14.3661(4)/90 4.170/150.1175.248/398.842[24]
1.4-diaminobutane, C4H8(NH3)22+ Ijms 24 13020 i0104.322/86.439
44[C4H14N2]2[UO2(SO4)3](H2O)2 cc0–1:3–4 P 1 ¯ 8.4584(1)/100.8158(5)10.2830(1)/96.3926(5)15.2943(2)/112.5170(5) 4.170/150.1176.000/768.000[22]
45[C4H14N2][UO2(H2O)(SO4)2] cc2–1:2–1 P 1 ¯ 7.4199(2)/79.1237(9)7.8380(2)/79.9015(9)12.0319(3)/83.1098(9) 4.000/128.0005.170/372.235[25]
46[C4H14N2][UO2F(SO4)]2 cc2–1:1–10P21/c6.7754(5)/908.4094(8)/93.245(3)14.1492(14)/90 3.170/114.1174.248/322.842[25]
47[C4H14N2][(UO2)2(SeO4)3(H2O)](H2O)2 cc2–2:3–4P21/c11.068(3)/9010.455(3)/114.555(19)20.266(3)/90 4.585/440.1565.644/1128.771[12,13]
48(C4H14N2)[(UO2)2(SO4)3(H2O)]·2H2Occ2–2:3–4P21/n10.9075(4)/9010.4513(4)/97.908(2)17.7881(7)/90 4.585/440.1565.644/1128.771[26]
49[C4H14N2][(UO2)(SO4)2(H2O)]·2H2Occ2–1:2–3P21/n8.8570(4)/907.3299(3)/95.140(2)20.4260(9)/90 4.000/256.0005.000/640.000[26]
1.5-diaminopentane, C5H10(NH3)22+ Ijms 24 13020 i0114.524/104.042
50[C5H16N2][UO2(SO4)2] cc2–1:2–21P21/c7.9825(1)/9019.8458(4)/111.6563(9)9.7868(2)/90 3.700/192.4235.170/744.469[22]
51[C5H16N2][(UO2)2(SeO4)3(H2O)] cc2–2:3–10P218.0491(11)/9012.2633(16)/99.918(11)10.7239(16)/90 4.585/220.0785.555/522.131[12,13]
1.6-diaminohexane, C6H12(NH3)22+ Ijms 24 13020 i0124.700/122.211
52[C6H18N2][UO2(SO4)2]H2O cc1–1:2–12P21/m10.1385(3)/906.9537(3)/99.287(2)11.7233(4)/90 3.393/88.2114.880/478.242[22]
53[C6H18N2][(UO2)2(SeO4)3(H2O)] cc2–2:3–10P218.4020(18)/9012.411(3)/102.951(17)10.923(2)/90 4.585/220.0785.644/564.386[12,13]
1.7-diaminoheptane, C7H14(NH3)22+ Ijms 24 13020 i0134.858/140.881
54[C7H20N2][(UO2)2(SeO4)3(H2O)](H2O)cc2–2:3–10P218.7100(16)/9012.4174(14)/101.348(14)10.8838(18)/90 4.585/220.0785.807/650.424[12,13]
1.8-diaminooctane, C8H16(NH3)22+ Ijms 24 13020 i0145.000/160.000
55[C8H22N2][(UO2)2(SeO4)3(H2O)] cc2–2:3–10P218.7793(16)/9012.4874(15)/100.609(14)10.9331(18)/90 4.585/220.0785.807/650.424[12,13]
1.9-diaminononane, C9H18(NH3)22+ Ijms 24 13020 i0155.129/179.525
56[C9H24N2][(UO2)(SeO4)(SeO2OH)] (NO3) cc2–1:2–4 P 1 ¯ 10.7480(7) /109.960(1)13.8847(9)/103.212(2)14.6363(10)/90.409(1) 4.700/244.4236.700/1393.691[27]
57[C9H24N2]2[(UO2)3(SeO4)5(H2O)2](H2O)x cc2–3:5–4P63/mmc19.5572(5)/9019.5572(5)/9047.878(2)/120 4.670/2017.4085.755/5190.982[28]
1.10-diaminodecane, C10H20(NH3)22+ Ijms 24 13020 i0165.248/199.421
58[C10H26N2][(UO2)(SeO4)2(H2O)] (H2SeO4)0.85(H2O)2 cc1–1:2–1 P 1 ¯ 7.5461(6)/77.678(6)14.9910(12)/85.463(6)22.3789(17)/82.717(6) 5.000/320.0006.895/1640.967[19]
59[C10H26N2][(UO2)(SeO4)2] (H2SeO4)0.5(H2O) cc2–1:2–4C2/c29.280(2)/9013.3013(10)/93.295(5)11.4513(7)/90 3.700/192.4235.879/1375.665[19]
1.12-diaminododecane, C12H24(NH3)22+ Ijms 24 13020 i0175.459/240.215
60[C12H30N2]3[H3O]2[(UO2)4(SeO4)8] (H2O)5 cc2–1:2–13P21/n11.3437(7)/9024.8042(12)/96.701(5)29.2496(19)/90 5.700/1185.6917.622/6006.177[29]
Dimethylamine, C2H6NH2+ Ijms 24 13020 i0183.459/38.054
61[C2H8N]2[(UO2)(SeO4)2(H2O)] cc1–1:2–1P2121217.5363(7)/9012.2021(11)/9016.7601(16)/90 4.000/256.0005.248/797.685[30]
62[C2H8N]2[(UO2)2(SeO4)3(H2O)]cc2–2:3–4P21212111.2154(5)/9011.2263(5)/9016.9138(8)/90 4.585/440.1565.524/1016.335[30]
63[C2H8N]3[H5O2][(UO2)2(SeO4)3(H2O)2]2 (H2O)5cc2–2:3–5P21/c12.451(5)/9031.126(5)/120.39(2)14.197(4)/90 5.524/1016.3356.658/2689.917[30]
64[C2H8N]2[H3O][(UO2)3 (SeO4)4(HSeO3)(H2O)](H2SeO3)0.2cc2–3:5–3P21/m8.3116(4)/9018.6363(8)/97.582(1)11.5623(5)/90 4.264/289.9475.078/619.550[30]
65[C2H8N][(H5O2)(H2O)] [(UO2)2(SeO4)3(H2SeO3)](H2O) cc2–1:2–14P21/n14.7979(8)/9010.0238(6)/111.628(1)16.4176(9)/90 4.755/513.5285.672/1157.175[31]
66[C2H8N]3[C2H7N][(UO2)3(SeO4)4 (HSeO3)(H2O)] cc2–3:5–3Pnma11.6591(11)/9014.9556(17)/9022.194(2)/90 4.472/715.5085.607/1883.819[30]
67[C2H8N]3[H3O][(UO2)3(SeO4)4(SeO3) (H2O)](H2O) cc2–3:5–3P21/m8.941(2)/9019.300(4)/97.510(4)11.377(3)/90 4.329/303.0505.599/996.681[30]
Isopropylamine, C3H7NH3+ Ijms 24 13020 i0193.807/53.303
1[C3H10N]2[(UO2)6(SO4)7(H2O)2] frameworkC222110.2560(2)/9018.4062(4)/9022.8900(4)/90 4.900/578.1525.454/949.072This work
2[C3H10N]2[(UO2)2(SeO4)3(H2O)](H2O) cc2–2:3–4P21/c11.4644(2)/9011.2426(2)/99.421(2) 18.7555(4)/90 4.585/440.1565.781/1271.899This work,[12,13]
3[C3H10N]2[(UO2)2(SO4)3(H2O)](H2O) cc2–2:3–4P21/c11.0470(1)/9010.8926(1)/100.180(1)18.5397(2)/90 4.585/440.1565.781/1271.899This work
4[C3H10N](H3O)[(UO2)2 (SeO4)3(H2O)](H2SeO3)cc2–2:3–4P21/c11.2894(4)/9011.1012(3)/94.717(3)18.1368(6)/90 4.585/440.1565.585/1072.313This work
Tert-butylamine, C4H9NH3+ Ijms 24 13020 i0204.087/69.487
68[C4H12N]2[(UO2)(SeO4)2(H2O)] cc2–1:2–3C2/c27.212(10)/907.372(3)/117.75(2)23.113(7)/90 4.000/256.0005.644/1128.771[20]
69[C4H12N]2[(UO2)2(SeO4)3(H2O)] cc2–2:3–4P21/c11.3478(14)/9011.3850(9)/91.865(11)18.959(3)/90 4.585/440.1565.858/1359.052[12,13]
Tetramethylammonium, C4H12N+ Ijms 24 13020 i0214.087/69.487
70[C4H12N][(UO2)(SO4)(H2O)2]Cl cc1–1:1–2P218.989(6)/906.877(4)/109.77(4)10.981(8)/90 3.807/106.6065.000/320.000[32]
71[C4H12N][(UO2)(SO4)(NO3)] cc1–1:2–12C2/m21.106(1)/906.9350(3)/97.5468(18)8.4284(5)/90 3.252/78.0394.306/249.763[33]
72[C4H12N][(UO2)(SeO4)(NO3)] cc1–1:2–12C2/m21.244(5)/907.1092(11)/97.693(17)8.6581(18)/90 3.252/78.0394.375/280.000[34]
73[C4H12N]2[(UO2)6(SO4)7(H2O)2] frameworkC222110.3466(2)/9018.5415(3)/9022.7001(4)/90 4.800/527.9505.487/976.681[35]
Triethylamine, C6H15NH+ Ijms 24 13020 i0224.524/104.042
74[C6H16N][H3O][(UO2)2(SeO4)3(H2O)] (H2O) cc2–2:3–4P218.8162(16)/9012.4459(15)/103.695(14)10.8212(19)/90 4.585/220.0785.755/621.528[12,13]
75[C6H16N][H5O2][(UO2)2(SeO4)3(H2O)] cc2–2:3–10P218.8477(3)/9012.4835(5)/103.382(1)10.8373(4)/90 4.585/220.0785.755/621.528[36]
76(H5O2)[C6H16N][(UO2)2(SeO4)3(H2O)]cc2–2:3–10P21/c10.753(1)/9012.3221(8)/91.050(9)18.142(2)/90 4.585/440.1565.755/1243.056[13]
Guanidine, CH6N3+ Ijms 24 13020 i0233.322/33.219
77[CH6N3]2[(UO2)(SO4)(H2O)2](NO3)2 (H2O) cc1–1:1–2P21/n12.3824(7)/907.0329(4)/99.598(2)21.5362(12)/90 3.807/213.2125.492/988.534[37]
78[CH6N3]2[(UO2)(SO4)2(H2O)](H2O)2 cc2–1:2–2C2/c11.220(8)/908.027(4)/101.00(7)18.681(8)/90 3.125/100.0004.440/372.955[38]
79[CH6N3]2[(UO2)2(SO4)3] cc2–2:3–14P212129.907(3)/909.597(3)/909.762(3)/90 3.440/144.4774.480/367.319[39]
80[CH6N3]2[(UO2)(SeO4)2(H2O)](H2O)1.5 cc2–1:2–2C2/c37.314(4)/907.1771(6)/109.267(8)13.2054(14)/90 4.000/256.0005.352/867.056[20]
81[CH6N3]3[(UO2)2(SeO4)3(HSeO4)](H2O)2 cc2–1:2–4P212121 10.7261(9)/90 13.9178(16)/90 18.3213(17)/90 4.755/513.5285.977/1506.275[20]
82[CH6N3]2[(UO2)2(SeO4)3] cc2–2:3–14P29.9448(15)/909.727(2)/90.213(12)10.1508(15)/90 4.440/186.4775.480/449.319[5]
Aminoguanidine, CH7N4+ Ijms 24 13020 i0243.585/43.020
83[CH7N4]2[(UO2)(SO4)2(H2O)] cc2–1:2–2C2/c11.297(2)/907.8336(16)/100.18(3)17.984(4)/90 3.125/100.0004.627/444.156[40]
1,2-diaminopropane, C3H12N22+ Ijms 24 13020 i0254.087/69.487
84[C3H12N2]2[(UO2)2(SO4)4(H2O)4](H2O)2 cc1–1:2–1 P 1 ¯ 7.3983(2)/95.1761(12)7.6333(2)/94.6412(13)12.5946(5)/96.578(2) 4.248/161.4215.285/412.261[41]
85[C3H12N2][UO2(H2O)(SO4)2] cc1–1:1–1 P 1 ¯ 7.3296(2)/92.0309(13)7.3702(2)/106.041(1)11.6822(2)/93.6783(9) 4.000/128.0005.044/332.930[42]
86[C3H12N2][UO2F(SO4)]2·H2O cc2–1:1–9Pnma13.5775(3)/9014.6180(4)/908.1168(2)/90 3.170/228.2354.752/912.313[24]
87[C3H12N2][(UO2)(SeO4)2(H2O)2](H2O) cc0–1:2–3 P 1 ¯ 7.5611(16)/94.604(18)7.7650(17)/94.405(17)12.925(3)/96.470(17) 4.248/161.4215.285/412.261[34]
N.N-dimethylethylene diamine, C4H14N22+ Ijms 24 13020 i0264.322/86.439
88[C4H14N2][UO2(SO4)2] cc2–1:2–20P2121219.3322(1)/909.7743(2)/9013.8897(3)/90 3.700/192.4235.044/665.860[43]
89[C4H14N2][(UO2)2(H2O)(SO4)3](H2O) cc2–2:3–4P21/c11.2460(2)/9010.5387(2)/92.9884(6)17.0432(3)/90 4.585/440.1565.555/1044.263[43]
90[C4H14N2][(UO2)(SeO4)2(H2O)] cc2–1:2–8 P 1 ¯ 6.853(2)/99.62(3)10.537(3)/94.45(3)10.574(3)/100.52(3) 4.000/128.0005.170/372.235[34]
91[C4H14N2][(UO2)2(SeO4)3(H2O)](H2O)cc2–2:3–4P21/c11.568(4)/9010.857(4)/95.545(11)17.229(7)/90 4.585/440.1565.555/1044.263[36]
Diethylenetriamine, C4H15N33+ Ijms 24 13020 i0274.459/98.107
92[C4H15N3][H3O]0.5[(UO2)2(SeO4)3 (H2O)](NO3)0.5 cc2–2:3–4P21/c11.1679(4)/98.019(1)10.9040(4)/9017.9913(6)/90 4.459/392.4305.615/1100.483[30]
1.3-diaminopentane, C5H16N22+ Ijms 24 13020 i0284.524/104.042
93[C5H16N2]2[(UO2)(SeO4)2(H2O)](NO3)2 cc1–1:2–1C2/c28.916(5)/908.0836(10)/110.909(11)11.9856(16)/90 3.125/100.0005.158/722.100[34]
N,N-Diethylethylenediamine, C6H18N22+ Ijms 24 13020 i0294.700/122.211
94[C3H8N]2[(UO2)2(SeO4)3(H2O)](H2O)cc2–2:3–4P21/c12.0301(15)/9010.7845(9)/91.865(10)17.490(2)/90 4.585/440.1565.728/1214.319[13]
Tetramethylethylenediamine, C6H18N22+ Ijms 24 13020 i0304.700/122.211
95[C6H18N2][(UO2)2(SO4)3(H2O)]cc2–2:3–4P218.4460(7)/9011.966(1)/104.043(2)10.6635(9)/90 4.585/220.0785.644/564.386[36]
1.2-ethylamino ethane, C6H18N22+ Ijms 24 13020 i0314.700/122.211
96[C6H18N2][(UO2)2(H2O)3(SO4)3] cc1–1:1–2
cc1–1:2–8		 P 1 ¯ 6.8234(1)/101.3691(6)8.7384(1)/98.1340(6)19.2381(4)/90.0480(11) 4.907/294.4135.807/650.424[42]
N,N-diethylethane-1,2-diamine, C6H18N22+ Ijms 24 13020 i0324.700/122.211
97[C6H18N2]2[UO2F(SO4)]4·H2O cc2–1:1–6 P 1 ¯ 10.8832(2)/75.6604(8)10.9386(2)/73.6101(7)16.5325(3)/89.7726(7) 5.285/412.2616.508/1184.419[24]
N,N,N′,N′-tetramethyl-1,3-propanediamine, C7H20N22+ Ijms 24 13020 i0334.858/140.881
98[C7H20N2][(UO2)2(SO4)3(H2O)] cc2–2:3–17 P 1 ¯ 6.7861(1)/88.6230(9)8.5143(1)/81.6364(8)19.0442(3)/84.8577(6) 4.585/220.0785.728/607.160[44]
N-(3-aminopropyl)-1,3-propanediamine, N3C6H203+ Ijms 24 13020 i0344.858/140.881
99(N3C6H20)(H5O2)[(UO2)4(SO4)6(H2O)2]· 4H2Occ2–2:3–4P21/n10.8576(1)/9010.4120(1)/97.518(1)17.8726(3)/90 4.585/440.1565.858/1359.052[45]
100(N3C6H20)[(UO2)(SO4)2(SO3OH)]·H2Occ1–1:3–2 P 1 ¯ 7.9164(1)/92.892(1)11.0632(1)/97.938(1)11.3354(1)/107.497(1) 4.248/161.4215.672/578.587[45]
Triethylenetetramine, C6H22N44+ Ijms 24 13020 i0355.000/160.000
101[C6H22N4][UO2(H2O)(SO4)2]2(H2O)6 cc1–1:2–8 P 1 ¯ 6.7186(5)/72.337(2)9.2625(7)/89.198(2)13.1078(9)/70.037(1) 4.000/128.0005.358/439.319[46]
102[C6H22N4][UO2(SO4)2]2 cc2–1:2–20Pbca9.3771(2)/9012.9523(3)/9018.9065(6)/90 3.700/384.8464.858/1127.052[47]
103[C6H22N4][(UO2)(SeO4)2(H2O)](H2O) cc2–1:2–3P21/n13.002(2)/907.962(1)/114.077(2)14.754(2)/90 4.000/256.0005.129/718.100[10]
104[N4C6H22][UO2(H2O)(SO4)2]2(H2O)6cc1–1:2–8 P 1 ¯ 6.7318(1)/72.3395(6) 9.2975(1)/89.1401(7) 13.1457(3)/70.0267(12) 4.000/128.0005.358/439.319[47]
Tris(2-aminoethyl)-amine, C6H21N44+ Ijms 24 13020 i0365.000/160.000
105[C6H21N4][(UO2)(SeO4)2(HSeO4)] cc1–1:3–2P21/m9.2218(6)/9012.2768(9)/116.165(1)9.4464(7)/90 3.616/137.4214.931/512.846[10]
106(N4C6H22)[(UO2)2(SO4)4(H2O)2]·3H2Occ2–1:2–2P21/n7.4982(1)/9016.9531(5)/90.729(2)11.4496(2)/90 4.000/256.0005.700/1185.691[45]
107[C6H22N4]2[(UO2)2(SO4)6](H2O) cc0–1:3–4 P 1 ¯ 11.2315(1)/88.4073(5)13.2136(1)/74.5896(5)14.3521(2)/66.5370(6) 5.170/372.2356.687/1377.419[22]
1,5,8,12-tetraazadodecane, C8H26N44+ Ijms 24 13020 i0375.248/199.421
108[C8H26N4][(UO2)(SeO4)2(H2O)](H2O) cc2–1:2–2P21/n7.8198(11)/9016.516(3)/90.662(11)11.6831(16)/90 4.000/256.0005.285/824.523[48]
109[C8H26N4]0.5[(UO2)2(SO4)3(H2O)](H2O)2 cc2–2:3–12P21/n11.8400(2)/9010.3190(2)/107.7718(9)16.5919(4)/90 4.585/440.1565.615/1100.483[49]
Tetraethylenepentamine, C8H28N55+ Ijms 24 13020 i0385.358/219.660
110[C8H28N5]2[(UO2)5(H2O)5(SO4)10]H2O cc2–1:2–2Pbnm7.7638(5)/9014.16890(5)/9056.46930(5)/90 5.372/1719.0176.409/4229.773[47]
Imidazole, C3H5N2+ Ijms 24 13020 i0393.322/33.219
111[C3H5N2]2[(UO2)2(SO4)3] cc2–2:3–14P2121219.7683(3)/9010.0252(3)/9019.9136(7)/90 4.392/368.9555.358/878.639[42]
Pyrazine, C4H5N22+ Ijms 24 13020 i0403.459/38.054
112(C4H5N2)2[(UO2)(SeO4)2(H2O)]cc2–1:2–1C2/c18.2026(8)/907.9997(3)/106.947(2)11.6866(5)/90 3.125/100.0004.301/326.842[50]
113(C4H5N2)2[(UO2)2(SeO4)3(H2O)]·3H2Occ2–2:3–11 P 1 ¯ 8.8130(5)/108.286(2)11.5642(6)/94.279(2)13.1308(7)/105.157(2) 4.755/256.7645.781/635.950[50]
114(H3O)(C4H5N2)2[(UO2)3(SeO4)5(H2O)]· H2Occ2–3:5–3Pbcm11.573(3)/9019.220(6)/9014.465(5)/90 4.472/715.5085.469/1465.712[50]
Pyridine, C5H6N+ Ijms 24 13020 i0413.585/43.020
115 1[C5H6N][(UO2)(SeO4)(HSeO3)] cc2–1:2–4P21/n8.993(3)/9013.399(5)/108.230(4)10.640(4)/90 --[51]
116[C5H6N]2[(UO2)2(SeO4)3] cc2–2:3–14Pccn9.987(7)/9010.251(7)/9020.957(14)/90 3.440/288.9554.589/789.318[52]
117(C5H6N)2[(UO2)2(SeO4)3(H2O)]∙3H2Occ2–2:3–10P21/n10.6354(4)/9012.3334(5)/103.182(1)18.8810(8)/90 4.585/440.1565.755/1243.056[50]
Azetidine, C3H8N+ Ijms 24 13020 i0423.585/43.020
118[C3H8N]2[(UO2)2(SeO4)3(H2O)]cc2–2:3–4P21212110.8620(5)/9011.1105(5)/9017.8815(8)/90 4.585/440.1565.585/1072.313[53]
4-aminopyridine, C5H7N2+ Ijms 24 13020 i0433.907/58.603
119[C5H7N2]2[(UO2)(SO4)2]cc1–1:2–12 P 1 ¯ 7.0126(9)/68.187(5)10.3352(13)/78.940(5)13.8027(19)/71.339(3) 3.700/96.2115.426/466.659[37]
Benzylamine, NC7H10+ Ijms 24 13020 i0444.170/75.059
120[NC7H10]2[(UO2)2(SO4)3]·H2Occ2–2:3–14P21/n10.3238(2)/909.1710(2)/91.414(2)27.1113(7)/90 4.392/368.9555.907/1417.654[45]
121[C7H10N]2[(UO2)(SeO4)2(H2O)](H2O) cc2–1:2–2Pna21 24.221(2)/90 11.9169(11)/90 7.4528(7)/90 4.000/256.0005.781/1271.899[10]
Piperazine, C4H12N22+ Ijms 24 13020 i0454.170/75.059
122[C4H12N2][UO2(H2O)(SO4)2] cc1–1:2–1C2/c14.7676(3)/907.6585(2)/104.837(2)11.6807(2)/90 3.125/100.0004.146/281.947[54]
123[C4H12N2][(UO2)(SeO4)2 (H2O)] cc1–1:2–1C2/c15.7651(10)/907.4093(5)/101.121(2)11.9639(8)/90 3.125/100.0004.146/281.947[50]
124[C4H12N2]0.5[(UO2)(HSeO3)(SeO3)] cc2–1:2–20P21/c10.9378(5)/908.6903(4)/90.3040(8)9.9913(5)/90 3.585/172.0784.392/368.955[55]
1-methylpiperazine, C5H14N22+ Ijms 24 13020 i0464.392/92.239
125[C5H14N2][UO2(H2O)(SO4)2] cc1–1:2–1 P 1 ¯ 8.0031(2)/72.704(1)8.1873(2)/81.7766(11)10.8911(3)/78.7917(9) 4.000/128.0005.209/385.500[56]
2-methylpiperazine, C5H14N22+ Ijms 24 13020 i0474.392/92.239
126[C5H14N2][UO2(H2O)(SO4)2] cc1–1:2–4 P 1 ¯ 10.7537(2)/87.998(1)11.4297(2)/79.660(1)11.5797(2)/80.6313(6) 5.000/320.0006.209/918.999[54]
127[C5H14N2][UO2F(H2O)(SO4)]2 cc2–1:1–7P21/n8.4354(2)/9015.5581(4)/96.666(1)14.8442(6)/90 4.585/440.1565.585/1072.313[24]
Homopiperazine, C5H14N22+ Ijms 24 13020 i0484.392/92.239
128[C5H14N2]2[UO2(SO4)3] cc0–1:3–2C2/c14.4975(3)/9011.9109(3)/110.475(1)13.0157(3)/90 3.281/118.1174.940/592.827[43]
129[C5H14N2][UO2(H2O)(SO4)2] cc1–1:1–2P221217.6955(2)/9011.7717(3)/9014.7038(4)/90 4.125/264.0004.125/264.000[43]
1.4-diaminocyclohexane, C6H16N22+ Ijms 24 13020 i0494.585/110.039
130[N2C6H16][UO2F2(SO4)]cc1–1:1–13 P 1 ¯ 6.9105(2)/72.659(1)9.6605(2)/87.068(1)10.1033(2)/77.957(1) 3.322/66.4395.087/345.947[24]
131[C6H16N2][UO2F2(SO4)] cc2–1:1–14Pmmn6.9503(1)/9017.2147(4)/907.0867(1)/90 2.948/106.1174.309/534.320[24]
132[C6H16N2][UO2(SO4)2]·2H2O cc1–1:2–12 P 1 ¯ 6.7813(1)/76.7537(7)10.0636(2)/75.6074(7)12.9753(3)/74.3971(13) 3.700/96.2115.426/466.659[57]
Azetidinopropaneamine, C6H16N2+ Ijms 24 13020 i0504.585/110.039
133[C6H16N2][(UO2)2(SeO4)3(H2O)](H2O)cc2–2:3–4P21/c11.3575(5)/9011.021(5)/90.608(1)17.8038(8)/90 4.585/440.1565.728/1214.319[53]
134[C3H8N]2(H5O2)[(UO2)2(SO4)3(HSO4)]cc2–1:2–13P21/n8.677(3)/9010.294(3)/97.521(7)26.474(8)/90 4.755/513.5285.858/1359.052[53]
1-ethyl-3-methyl imidazolium, C6H11N2+ Ijms 24 13020 i0514.248/80.711
135 1[C6H11N2]2[(UO2)(SO4)2]cc1–1:2–12C2/c31.90(1)/909.383(5)/93.999(7)13.770(7)/90 --[58]
136[C6N2H11](Na)[(UO2)4(SO4)2(OH)2(O)2]· 3(H2O)5 2 4 3 3 2P21/c17.182(5)/908.852(3)/100.693(4)17.162(5)/90 4.755/513.5285.803/1288.360[59]
137[C6N2H11](H9O4)[(UO2)(SO4)2]cc1–1:2–12 P 1 ¯ 6.9504(11)/95.993(2)9.9247(15)/95.024(2)14.966(2)/103.323(2) 3.700/96.2115.931/723.550[59]
138[C6N2H11]2[(UO2)2(SO4)3(H2O)]cc2–2:3–22 P 1 ¯ 9.5715(11)/81.803(1)10.4399(12)/81.394(1)13.7023(16)/86.480(1) 4.585/220.0785.954/738.320[59]
139[C6N2H11]2[(UO2)2(SO4)3(H2O)2]·2(H2O)cc1–2:3–3P21/n12.952(2)/9019.302(3)/116.891(2)13.224(2)/90 4.755/513.5286.150/1746.528[59]
140[C6N2H11][(UO2)2(SO4)(OH)(O)]5 2 4 3 3 2 P 1 ¯ 8.859(2)/107.671(3)8.926(2)/97.350(3)9.893(3)/104.502(3) 3.807/106.6065.044/332.930[59]
1-(3-aminopropyl) imidazole, N3C6H13+ Ijms 24 13020 i0524.459/98.107
141[N3C6H13][(UO2)(SO4)2]cc1–1:2–12 P 1 ¯ 6.8164(1)/76.749(1)7.6357(1)/88.091(1)14.1979(2)/86.533(1) 3.700/96.2115.129/359.050[45]
1-butyl-3-methylimidazole, C8H15N2+ Ijms 24 13020 i0534.644/116.096
142[C8H15N2]2[(UO2)4(SeO3)5] 6 1 5 2 4 2 3 2Pnma18.860(2)/9018.010(2)/9011.140(1)/90 4.250/544.0005.455/1789.277[52]
2-piperazinoethylamine, C6H18N33+ Ijms 24 13020 i0544.755/128.382
143[C6H18N3][(UO2)2(H2O)(SO4)3(HSO4)] (H2O)4.5 cc2–1:2–12P21/a15.7673(4)/9010.5813(3)/99.9216(9)16.7710(5)/90 4.907/588.8276.129/1716.199[60]
144[C6H18N3]2[(UO2)5(H2O)(SO4)8](H2O)5 cc2–5:8–2P21/n21.5597(3)/9010.2901(2)/96.7436(7)22.8403(3)/90 5.858/1359.0526.989/3550.252[60]
1,4-bis(3-aminopropyl)piperazine, C10H28N44+ Ijms 24 13020 i0555.392/226.477
145(N4C10H28)0.5[(UO2)(SO4)2(H2O)]·H2Occ2–1:2–2P21/n7.5484(2)/9016.9859(4)/90.580(2)11.4581(3)/90 4.000/256.0005.322/851.508[45]
146[C10H28N4][(UO2)2(SO4)4] cc2–1:2–20Pbca9.5831(2)/9015.6060(3)/9018.1212(3)/90 3.700/384.8465.087/1383.790[61]
1,2,3-benzotriazole, C6H6N3+ Ijms 24 13020 i0563.907/58.603
147[C6H6N3][H5O2][(UO2)2(SeO4)3(H2O)]cc2–2:3–10P21/c12.167(3)/9012.316(3)/108.270(4)14.909(3)/90 4.585/440.1565.392/905.909[36]
148[C6H6N3][H7O3][(UO2)2(SO4)3(H2O)] (H2O)cc2–2:3–10C219.678(7)/9010.600(4)/95.979(7)10.925(4)/90 4.585/220.0785.720/594.846[36]
Melamine, C3H8N62+ Ijms 24 13020 i0574.087/69.487
149[C3H8N6][(UO2)2(SO4)3(H2O)](H2O) cc2–2:3–4P21/n11.1194(4)/9010.5921(3)/101.405(2)17.0143(6)/90 4.585/440.1565.459/960.860[62]
150[(C3H8N6)(SeO4)] [(UO2)(SeO4) (H2SeO3)2]cc2–1:3–6P21/c16.247(4)/908.680(2)/90.615(5)13.347(3)/90 4.644/464.3865.392/905.909[63]
4.4′-Bipyridine, C10H10N22+ Ijms 24 13020 i0584.459/98.107
151[C10H10N2][UO2(SO4)2]H2O cc1–1:2–12 P 1 ¯ 6.9507(1)/79.1992(7)7.7097(1)/80.1403(8)15.9200(4)/80.9717(14) 3.700/96.2115.248/398.842[42]
Terpyridine, C15H14N33+ Ijms 24 13020 i0595.000/160.000
152[C15H14N3][(UO2)(SO4)2](NO3)(H2O)2 cc1–1:2–12 P 1 ¯ 6.9732(7)/111.809(2)13.569(1)/102.386(2)13.641(1)/93.833(2) 3.700/96.2115.781/635.950[46]
1.4-diazabicyclo(2.2.2)octane, C6H14N22+ Ijms 24 13020 i0604.459/98.107
153[C6H14N2][UO2(H2O)(SO4)2] cc2–1:2–3P21/n8.6480(1)/907.7135(1)/90.7254(9)21.2554(3)/90 4.000/256.0005.248/797.685[54]
3-Aminotropane, C8H18N22+ Ijms 24 13020 i0614.807/134.606
154[C8H18N2](H5O2)2[(UO2)3(SeO4)5(H2O)] (H2O) cc2–3:5–5P21/n10.210(2)/9019.151(4)/98.959(3)17.819(3)/90 5.209/770.9996.340/2054.111[64]
155[C8H18N2](H5O2)2[(UO2)3(SO4)5(H2O)] (H2O) cc2–3:5–5P21/n10.147(3)/9018.726(6)/99.043(7)17.076(5)/90 5.209/770.9996.322/2023.017[64]
Cyclen, C8H24N44+ Ijms 24 13020 i0625.170/186.117
156[C8H24N4][(UO2)3(SO4)5] (H2O)3 cc2–3:5–2Pna2116.8623(10)/9018.0113(11)/9010.1928(6)/90 5.087/691.8956.304/1991.995[64]
157(C8H24N4)(H3O)2[(UO2)4(SeO4)7(H2O)] (H2O)6.75 cc2–4:7–3 P 1 ¯ 8.7587(14)/73.807(3)13.067(2)/88.980(4)23.009(4)/86.129(3) 5.644/564.3866.977/1758.275[64]
12-crown-4 ether, C8H16O4 Ijms 24 13020 i0634.807/134.606
158[C8H16O4]0.5[UO2(SO4)(H2O)](H2O) cc1–1:1–2 P 1 ¯ 7.007(1)/91.31(1)8.0408(6)/93.60(2)10.776(2)/100.18(1) 3.585/86.0394.858/281.763[65]
159[C8H16O4]2[(H5O2)3(H9O4)] [(UO2)2(SeO4)3(H2O)]2 cc2–2:3–10P21/c10.7328(6)/9012.2828(5)/110.102(5)22.7085(17)/90 4.585/440.1566.087/1655.790[66,67]
15-crown-5-ether, C10H20O5 Ijms 24 13020 i0645.129/179.525
160[K@(C10H20O5)][(UO2)(SeO4)(HSeO4) (H2O)]cc1–1:2–1Pnma15.386(3)/9010.771(2)/9013.239(3)/90 3.382/229.9474.860/1030.319[68]
161[(H5O2)(H3O)3](C10H20O5)[(UO2)3 (SeO4)5(H2O)]cc2–3:5–3P21/m11.6754(5)/9018.9887(10)/112.282(3)12.2047(5)/90 4.399/325.5006.064/1491.859[66,67]
162[(H5O2)x(H3O)4-x](C10H20O5) [(UO2)3(SeO4)5(H2O)](H2O)ycc2–3:5–3C2/c24.2575(15)/9011.7501(7)/101.996(1)18.9243(12)/90 4.362/340.2616.012/1527.126[66,67]
18-crown-6 ether, C12H24O6 Ijms 24 13020 i0655.392/226.477
163[C12H24O6]0.5[(UO2)(SO4)(H2O)3] cc1–1:1–1P21/n9.314(5)/909.339(3)/103.62(3)16.734(3)/90 4.087/277.9475.248/797.685[65]
164[(H3O)@(C12H24O6)]2(H3O)8 [(UO2)14(SO4)19(H2O)4](H2O)20.5 frameworkI4/m28.023(1)/9028.023(1)/9019.6840(7)/90 5.313/1583.3126.531/4375.972[69]
165[K@(C12H24O6)][(UO2)(SeO4)(NO3)] (H2O) cc1–1:2–12P21/c7.2402(2)/9021.2024(7)/91.581(1)15.7322(5)/90 3.585/172.0785.858/1359.052[70]
166[(H3O)@(C12H24O6)]K[H3O]2 [(UO2)3(SeO4)5](H2O)4 cc2–3:5–2
nanotubules		Ccmm 11.292(1)/90 37.158(1)/90 38.504(1)/90 5.264/1431.7906.622/4754.269[69]
Benzo-15-crown-5 ether, C14H20O5 Ijms 24 13020 i0665.285/206.131
167[C14H20O5]0.5[(UO2)(SO4)(H2O)2](H2O) cc1–1:1–2 P 1 ¯ 6.908(2)/79.46(2)8.717(4)/75.28(2)13.578(2)/89.98(3) 3.807/106.6065.524/508.168[65]
Thiourea, CN2H4S Ijms 24 13020 i0673.000/24.000
168[CN2H4S]2[UO2(SO4)2]·0.3H2Occ1–1:2–12P2121216.9283(1)/9013.3983(3)/9015.2250(3)/90 3.700/192.4235.044/665.860[71]
Chloroacetamide, ClCH2CONH2 Ijms 24 13020 i0683.322/33.219
169(C2H4NCOCl)[UO2(SO4)(H2O)2]cc1–1:1–2 P 1 ¯ 6.892(3)/104.40(3) 8.786(6)/109.71(3) 9.494(6)/90.33(3) 3.807/106.6064.524/208.084[72]
Choline, C5H12NO+ Ijms 24 13020 i0694.248/80.711
170[C5H12NO][(UO2)(SeO4)Cl(H2O)] cc2–1:1–1P21/n10.745(4)/9011.236(4)/114.580(5)12.477(4)/90 3.585/172.0785.044/665.860[73]
3-hydroxypiperidine, C5H7NO+ Ijms 24 13020 i0703.807/53.303
171[(C5H7NO)2(H2O)][(UO2)2(SeO4)3 (H2O)2](H2O)cc2–2:3–11 P 1 ¯ 9.4248(7)/85.456(1)11.2711(8)/79.571(1)13.1059(10)/73.439(1) 4.585/220.0785.781/635.950[36]
Carbamoylguanidine, C2N4H7O22+ Ijms 24 13020 i0713.907/58.603
172[C2N4H7O][(UO2)(SO4)(OH)](H2O)0.5 6 1 5 2 4 2 3 2P21/c10.5135(7)/9011.3744(7)/110.880(2)9.2731(5)/90 3.170/114.1174.747/503.160[74]
1-(hydroxyethyl)-5-nitroimidazole (Metronidazole), C6H10N3O3+ Ijms 24 13020 i0724.459/98.107
173[(C6H10N3O3)(H5O2)2(H2O)][(H5O2)3 (H2O)][(UO2)5(SO4)8(H2O)]cc2–5:8–2P2/c18.1693(17)/9010.0732(10)/103.427(2)30.098(3)/90 5.858/1359.0526.858/3182.103[75]
Glycine, C₂H₅NO₂+ Ijms 24 13020 i0733.322/33.219
174[(glyH2+)(H2O)]2[(UO2)(SO4)2(H2O)]cc2–1:2–2C2/c11.5914(5)/907.3412(3)/103.993(2)23.5958(9)/90 3.125/100.0004.684/468.386[76]
175 2[(glyH+)(H2O)]2[(UO2)(SeO4)2(H2O)]cc2–1:2–2C2/c11.5854(5)/907.3322(3)/103.623(2)23.5768(9)/90 3.125/100.0004.684/468.386[76]
176(glyH+)2[(UO2)(SeO4)2(H2O)cc2–1:2–2P2/c7.646(2)/909.496(3)/104.832(6)11.477(3)/90 3.125/100.0004.301/326.842[76]
177 3(glyH+)2[(UO2)(SO4)2(H2O)]cc2–1:2–2P2/c7.690(2)/909.505(3)/104.805(6)11.433(3)/90 3.125/100.0004.301/326.842[76]
α-alanine, C3H8NO2+ Ijms 24 13020 i0743.807/53.303
178(α-AlaH+)(H5O2)(H2O)3[(UO2)2(SO4)3 (H2O)2]cc2–2:3–5P21/c11.000(2)/9015.402(3)/91.320(6)13.688(3)/90 4.755/513.5285.644/1128.771[76]
179 4(α-AlaH+)(H5O2)(H2O)3[(UO2)2(SeO4)3 (H2O)2]cc2–2:3–5P21/c11.150(3)/9015.510(2)/92.00(2)13.500(5)/90 4.755/513.5285.644/1128.771[76]
β-alanine, C3H8NO2+ Ijms 24 13020 i0753.807/53.303
180(β-AlaH+)2[(UO2)(SO4)2(H2O)]cc1–1:2–1C2/c20.660(3)/907.3138(11)/91.934(5)11.8449(17)/90 3.125/100.0004.739/492.846[76]
181(β-AlaH+)2[(UO2)(SeO4)2(H2O)]cc1–1:2–1C2/c20.909(2)/907.4754(8)/92.589(2)12.1693(13)/90 3.125/100.0004.505/396.430[76]
Nicotinic acid, C6H6NO2+ Ijms 24 13020 i0763.907/58.603
182[(nicH+)(H5O2)(H2O)][(UO2)(SO4)2 (H2O)]cc2–2:3–10P21/n12.4322(9)/9011.9693(9)/106.574(2)14.5768(11)/90 4.585/440.1565.487/976.681[76]
183[(nicH+)(H5O2)(H2O)][(UO2)(SeO4)2 (H2O)]cc2–2:3–10P21/n12.616(2)/9012.329(3)/107.221(5)14.819(3)/90 4.585/440.1565.550/1032.284[76]
Isonicotinic acid, C6H6NO2+ Ijms 24 13020 i0773.907/58.603
184(IsonicH+)2[(UO2)(SO4)2(H2O)]cc1–1:2–1 P 1 ¯ 8.5774(9)/97.034(2)11.2800(12)/105.214(2)11.4608(12)/106.737(2) 4.000/128.0005.524/508.168[76]
185(IsonicH+)2[(UO2)(SeO4)2(H2O)]cc1–1:2–1 P 1 ¯ 8.629(2)/98.22(5)11.588(3)/105.180(4)11.588(3)/105.180(4) 5.044/166.4656.524/600.168[76]
Protonated morpholino-N-acetic acid, C6H6O3+ Ijms 24 13020 i0783.907/58.603
186Na(C6H6O3)[(UO2)2(SeO4)3(H2O)](H2O)2cc2–2:3–10P21/c10.7767(5)/9012.2679(5)/92.126(1)17.9043(8)/90 4.585/440.1565.728/1214.319[77]
187Na2(SO3OH)(C6H6O3)[(UO2)(SO4)2]cc1–1:2–12 P 1 ¯ 6.860(3)/85.186(6)10.546(4)/88.017(5)13.047(5)/79.752(5) 3.700/96.2115.426/466.659[77]
Threonine, C4H9NO3+ Ijms 24 13020 i0794.087/69.487
188[(TrhH+)(H2O)]2[(UO2)2(SO4)3(H2O)]cc2–2:3–4P21212110.5155(6)/9010.516(1)/9017.3804(12)/90 4.585/440.1565.492/988.534[76]
189 5[(TrhH+)(H2O)]2[(UO2)2(SeO4)3(H2O)]cc2–2:3–4P21212110.5602(6)/9010.485(5)/9017.5804(2)/90 4.585/440.1565.492/988.534[76]
Trimethylglycine, C5H12NO2+ Ijms 24 13020 i0804.322/86.439
190[C5H12NO2][UO2(Cl)(SO4)(H2O)]cc2–1:1–1P21/n9.0486(7)/9012.5735(9)/111.4560(7)12.3064(9)/90 3.585/172.0785.000/640.000[78]
Protonated N-phenylglycine, C8H9NO2+ Ijms 24 13020 i0814.322/86.439
191Na(C6H5CH(NH2)CO2)7[(UO2)6(SO4)10] (H2O)3.5cc2–3:5–2
nanotubules		R3m44.001(10)/9044.001(10)/9010.367(2)/90 5.329/1119.1496.062/2218.650[79]
1-methyl-3-carboxy methylimidazolium, C6H10N2O2+ Ijms 24 13020 i0824.322/86.439
192(C7H15N2O2)(H3O)[(UO2)2(SO4)3(H2O)]· 1.5H2Occ2–2:3–4P21/n10.7858(6)/9010.7092(6)/98.493(1)19.776(1)/90 4.585/440.1565.755/1243.056[80]
N-(3-aminopropyl)-2-pyrrolidinone, C7H14N2O+ Ijms 24 13020 i0834.585/110.039
193(N2C6H17COOH)[(UO2)2(SO4)3(H2O)]cc2–2:3–4P21/c11.4656(3)/9010.6562(2)/99.604(3)17.7267(5)/90 4.585/440.1565.728/1214.319[45]
N,N′-bis(3,5-dicarboxylatophenyl)-4,4′-bipyridinium dihydrate, C26H16N2O82+ Ijms 24 13020 i0845.700/296.423
194(C26H16N2O8)0.5[(UO2)(SO4)(H2O)2]·H2Occ1–1:1–2C2/c6.8993(14)/9018.396(4)/93.191(7)27.847(5)/90 3.807/213.2125.426/933.318[81]
1—Structural data not available; 2—assumed to be the structural analog of 174; 3—assumed to be the structural analog of 176; 4—assumed to be the structural analog of 178; 5—assumed to be the structural analog of 188.
Table 2. Crystallographic data and refinement parameters for 1–4.
Table 2. Crystallographic data and refinement parameters for 1–4.
Compound1234
Crystallographic Data
Space GroupC2221P21/cP21/cP21/c
a [Å]10.2560(2)11.4644(2)11.0470(1)11.2894(4)
b [Å]18.4062(4)11.24259(17)10.8926(1)11.1012(3)
c [Å]22.8900(4)18.7555(4)18.5397(2)18.1368(6)
β [°]9099.421(2)100.180(1)94.717(3)
V [Å3]4321.03(15)2384.77(8)2195.77(4)2265.30(12)
Z4444
Data Collection Parameters
Angle range 2θ [o]6.94–55.007.12–52.006.49–55.006.65–55.00
Total reflections21,96728,65071,79018,562
Unique reflections4968465650275195
Reflections
with F2 > 2σ(F2)		4715432647734616
Rint, Rσ [%]4.19, 3.634.14, 2.937.86, 2.722.77, 2.93
Refinement Parameters
R1 (F2 > 2σ(F2)),
wR2 (F2 > 2σ(F2)) [%]		2.88, 6.612.29, 4.991.86, 4.482.44, 4.69
R1 and wR2 (all data) [%]3.12, 6.692.61, 5.092.02, 4.533.11, 4.86
S1.0521.0681.0481.024
ρmax, ρmin [e− Å−3]2.008/−1.9321.940/−1.0261.477/−1.7331.453/−0.883
CCDC2,285,0712,285,0722,285,0732,285,074
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Durova, E.V.; Kuporev, I.V.; Gurzhiy, V.V. Organically Templated Uranyl Sulfates and Selenates: Structural Complexity and Crystal Chemical Restrictions for Isotypic Compounds Formation. Int. J. Mol. Sci. 2023, 24, 13020. https://doi.org/10.3390/ijms241613020

AMA Style

Durova EV, Kuporev IV, Gurzhiy VV. Organically Templated Uranyl Sulfates and Selenates: Structural Complexity and Crystal Chemical Restrictions for Isotypic Compounds Formation. International Journal of Molecular Sciences. 2023; 24(16):13020. https://doi.org/10.3390/ijms241613020

Chicago/Turabian Style

Durova, Elizaveta V., Ivan V. Kuporev, and Vladislav V. Gurzhiy. 2023. "Organically Templated Uranyl Sulfates and Selenates: Structural Complexity and Crystal Chemical Restrictions for Isotypic Compounds Formation" International Journal of Molecular Sciences 24, no. 16: 13020. https://doi.org/10.3390/ijms241613020

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