A Comprehensive Investigation into the Crystallology, Molecule, and Quantum Chemistry Properties of Two New Hydrous Long-Chain Dibasic Ammonium Salts CnH2n+8N2O6 (n = 35 and 37)
Abstract
:1. Introduction
2. Results and Discussions
2.1. Descriptions of Crystal Structure
2.2. Hirshfeld Surface Analysis
2.3. Energy Frameworks
2.4. Quantum Chemical Calculations
2.4.1. Molecular Geometry Optimization
2.4.2. Frontier Molecular Orbitals
2.4.3. Density of States
2.4.4. Molecular Electrostatic Potential
3. Materials Methods
3.1. Sample Synthesis and Instruments
3.2. Basic Experimental Data
3.3. X-ray Crystallography
3.4. CrystalExplorer
3.5. Multiwfn
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Empirical Formula | C35H78N2O6 | C37H82N2O6 |
---|---|---|
Formula weight | 622.99 | 651.04 |
Temperature/K | 273.15 | 273(2) |
Crystal system | triclinic | triclinic |
Space group | P-1 | P-1 |
a/Å | 6.6497(8) | 6.6942(13) |
b/Å | 8.4340(9) | 8.4899(17) |
c/Å | 35.221(4) | 37.083(7) |
α/° | 90.747(2) | 92.15(3) |
β/° | 90.748(2) | 93.65(3) |
γ/° | 96.969(3) | 97.04(3) |
Volume/Å3 | 1960.4(4) | 2085.2(7) |
Z | 2 | 2 |
ρcalc g/cm3 | 1.055 | 1.037 |
μ/mm−1 | 0.07 | 0.068 |
F(000) | 700 | 732 |
Crystal size/mm3 | 0.44 × 0.18 × 0.07 | 0.12 × 0.11 × 0.1 |
Radiation | MoKα (λ = 0.71073) | MoKα (λ = 0.71073) |
2θ range for data collection/° | 4.626 to 48.998 | 5.984 to 55.108 |
Index ranges | −7 ≤ h ≤ 7, −9 ≤ k ≤ 9, −35 ≤ l ≤ 41 | −8 ≤ h ≤ 8, −11 ≤ k ≤ 11, −48 ≤ l ≤ 48 |
Reflections collected | 19,122 | 44,383 |
Independent reflections | 6446 (Rint = 0.0382, Rsigma = 0.0711) | 9598 (Rint = 0.1409, Rsigma = 0.1786) |
Data/restraints/parameters | 6446/0/392 | 9598/0/410 |
Goodness-of-fit on F2 | 1.12 | 0.991 |
Final R indexes [I ≤ 2σ (I)] | R1 = 0.1128, wR2 = 0.2502 | R1 = 0.0829, wR2 = 0.1593 |
Final R indexes (all data) | R1 = 0.1765, wR2 = 0.2793 | R1 = 0.2541, wR2 = 0.2113 |
∆ρmax/∆ρmin, e/Å3 | 0.21/−0.30 | 0.25/−0.19 |
Atoms | Bond Lengths (Å) | Atoms | Bond Angles (°) | ||
---|---|---|---|---|---|
SCXRD | DFT | SCXRD | DFT | ||
C1–C2 | 1.505(8) | 1.5047 | O1–C1–C2 | 116.2(5) | 116.18 |
C1–O1 | 1.237(6) | 1.2369 | O1–C1–O2 | 124.5(5) | 124.53 |
C1–O2 | 1.243(7) | 1.2428 | O2–C1–C2 | 119.3(5) | 119.29 |
C2–C3 | 1.478(9) | 1.4772 | C3–C2–C1 | 117.3(6) | 117.36 |
C3–C4 | 1.500(8) | 1.5001 | C2–C3–C4 | 115.4(6) | 115.39 |
C4–C5 | 1.503(8) | 1.503 | C3–C4–C5 | 113.8(6) | 113.77 |
C5–C6 | 1.494(8) | 1.4941 | C6–C5–C4 | 115.1(6) | 115.06 |
C6–C7 | 1.496(9) | 1.4965 | C5–C6–C7 | 114.6(6) | 114.58 |
C7–C8 | 1.495(8) | 1.495 | C8–C7–C6 | 114.9(6) | 114.95 |
C8–C9 | 1.494(9) | 1.4941 | C9–C8–C7 | 115.2(6) | 115.19 |
C9–C10 | 1.502(8) | 1.5023 | C8–C9–C10 | 115.4(6) | 115.45 |
C10–C11 | 1.494(9) | 1.4939 | C11–C10–C9 | 114.2(6) | 114.22 |
C11–C12 | 1.502(9) | 1.5021 | C10–C11–C12 | 115.0(6) | 115.02 |
C12–C13 | 1.491(9) | 1.4906 | C13–C12–C11 | 114.5(6) | 114.60 |
C13–C14 | 1.500(9) | 1.4999 | C12–C13–C14 | 115.4(7) | 115.48 |
C14–C15 | 1.487(11) | 1.4867 | C15–C14–C13 | 113.8(7) | 113.77 |
C15–C16 | 1.492(12) | 1.4930 | C14–C15–C16 | 114.9(9) | 114.87 |
C17–C18 | 1.496(7) | 1.4961 | N2–C17–C18 | 113.5(4) | 113.46 |
C17–N2 | 1.467(7) | 1.4672 | C17–C18–C19 | 109.6(4) | 109.62 |
C18–C19 | 1.499(7) | 1.4999 | N1–C19–C18 | 111.4(4) | 111.43 |
C19–N1 | 1.474(6) | 1.4747 | O3–C20–C21 | 120.1(5) | 120.10 |
C20–C21 | 1.506(8) | 1.5061 | O4–C20–C21 | 116.0(6) | 115.97 |
C20–O3 | 1.240(7) | 1.2394 | O4–C20–O3 | 124.0(6) | 123.94 |
C20–O4 | 1.232(7) | 1.2319 | C22–C21–C20 | 118.2(5) | 118.18 |
C21–C22 | 1.495(8) | 1.4952 | C21–C22–C23 | 112.2(5) | 112.22 |
C22–C23 | 1.514(8) | 1.5136 | C24–C23–C22 | 114.1(5) | 114.14 |
C23–C24 | 1.503(9) | 1.503 | C23–C24–C25 | 113.1(5) | 113.03 |
C24–C25 | 1.503(8) | 1.5028 | C26–C25–C24 | 114.9(6) | 114.91 |
C25–C26 | 1.491(9) | 1.4908 | C25–C26–C27 | 114.3(6) | 114.31 |
C26–C27 | 1.508(8) | 1.5079 | C28–C27–C26 | 115.4(6) | 115.45 |
C27–C28 | 1.497(9) | 1.4968 | C27–C28–C29 | 114.2(6) | 114.18 |
C28–C29 | 1.503(9) | 1.5025 | C28–C29–C30 | 113.7(6) | 113.70 |
C29–C30 | 1.503(9) | 1.503 | C31–C30–C29 | 114.3(6) | 114.26 |
C30–C31 | 1.502(9) | 1.5023 | C32–C31–C30 | 114.1(7) | 114.12 |
C31–C32 | 1.490(10) | 1.4903 | C31–C32–C33 | 115.5(7) | 115.59 |
C32–C33 | 1.499(10) | 1.4975 | C34–C33–C32 | 113.8(8) | 113.81 |
C33–C34 | 1.496(12) | 1.4963 | C35–C34–C33 | 116.8(10) | 116.64 |
C34–C35 | 1.438(14) | 1.4375 |
Atoms | Bond Lengths (Å) | Atoms | Bond Angles (°) | ||
---|---|---|---|---|---|
SCXRD | DFT | SCXRD | DFT | ||
C1–C2 | 1.510(3) | 1.5105 | O1–C1–C2 | 118.7(2) | 118.74 |
C1–O1 | 1.256(3) | 1.2563 | O2–C1–C2 | 117.3(2) | 117.32 |
C1–O2 | 1.248(3) | 1.2484 | O2–C1–O1 | 123.9(2) | 123.93 |
C2–C3 | 1.480(3) | 1.4794 | C3–C2–C1 | 118.3(2) | 118.28 |
C3–C4 | 1.508(3) | 1.5080 | C2–C3–C4 | 116.2(2) | 116.21 |
C4–C5 | 1.501(3) | 1.5013 | C5–C4–C3 | 114.4(2) | 114.41 |
C5–C6 | 1.506(3) | 1.5058 | C4–C5–C6 | 115.4(2) | 115.44 |
C6–C7 | 1.503(3) | 1.5031 | C7–C6–C5 | 115.1(2) | 115.13 |
C7–C8 | 1.512(3) | 1.5121 | C6–C7–C8 | 115.1(2) | 115.15 |
C8–C9 | 1.501(3) | 1.5003 | C9–C8–C7 | 115.2(2) | 115.22 |
C9–C10 | 1.505(3) | 1.5046 | C8–C9–C10 | 115.4(2) | 115.39 |
C10–C11 | 1.507(3) | 1.5067 | C9–C10–C11 | 115.3(2) | 115.26 |
C11–C12 | 1.514(3) | 1.5144 | C10–C11–C12 | 115.2(2) | 115.24 |
C12–C13 | 1.508(3) | 1.5075 | C13–C12–C11 | 115.0(2) | 115.02 |
C13–C14 | 1.510(3) | 1.5105 | C12–C13–C14 | 114.4(2) | 114.38 |
C14–C15 | 1.503(4) | 1.5028 | C15–C14–C13 | 115.1(2) | 115.12 |
C15–C16 | 1.501(4) | 1.5006 | C16–C15–C14 | 114.9(3) | 114.87 |
C16–C17 | 1.511(4) | 1.5111 | C15–C16–C17 | 115.1(3) | 115.06 |
C18–C19 | 1.508(3) | 1.5083 | N2–C18–C19 | 113.12(18) | 113.1170 |
C18–N2 | 1.481(3) | 1.4818 | C18–C19–C20 | 109.45(18) | 109.4540 |
C19–C20 | 1.517(3) | 1.5171 | N1–C20–C19 | 111.81(17) | 111.8120 |
C20–N1 | 1.477(3) | 1.4770 | O3–C21–C22 | 119.2(2) | 119.14 |
C21–C22 | 1.511(3) | 1.5111 | O4–C21–C22 | 116.4(2) | 116.40 |
C21–O3 | 1.256(3) | 1.2557 | O4–C21–O3 | 124.5(2) | 124.47 |
C21–O4 | 1.235(3) | 1.2342 | C23–C22–C21 | 118.9(2) | 118.93 |
C22–C23 | 1.505(3) | 1.5056 | C22–C23–C24 | 113.5(2) | 113.53 |
C23–C24 | 1.515(3) | 1.5149 | C25–C24–C23 | 115.5(2) | 115.53 |
C24–C25 | 1.500(3) | 1.5001 | C24–C25–C26 | 114.1(2) | 114.08 |
C25–C26 | 1.509(3) | 1.5091 | C27–C26–C25 | 115.8(2) | 115.79 |
C26–C27 | 1.505(3) | 1.5044 | C26–C27–C28 | 115.1(2) | 115.11 |
C27–C28 | 1.506(3) | 1.5064 | C27–C28–C29 | 115.7(2) | 115.75 |
C28–C29 | 1.507(3) | 1.507 | C28–C29–C30 | 115.2(2) | 115.18 |
C29–C30 | 1.508(3) | 1.5083 | C31–C30–C29 | 115.2(2) | 115.15 |
C30–C31 | 1.503(3) | 1.5033 | C30–C31–C32 | 115.0(2) | 114.99 |
C31–C32 | 1.512(3) | 1.5115 | C33–C32–C31 | 115.0(2) | 115.04 |
C32–C33 | 1.507(3) | 1.507 | C34–C33–C32 | 114.9(2) | 114.95 |
C33–C34 | 1.505(3) | 1.5049 | C33–C34–C35 | 115.7(3) | 115.77 |
C34–C35 | 1.506(4) | 1.5059 | C36–C35–C34 | 115.2(3) | 115.14 |
C35–C36 | 1.488(4) | 1.4881 | C37–C36–C35 | 116.8(3) | 116.80 |
C36–C37 | 1.481(4) | 1.4814 |
D-H…A | d(D-H)/Å | d(H-A)/Å | d(D-A)/Å | D-H-A/° |
---|---|---|---|---|
N1-H1A…O3 i | 0.89 | 1.89 | 2.756(7) | 162.8 |
N1-H1B…O1 ii | 0.89 | 1.91 | 2.797(6) | 175.4 |
N1-H1C…O4 iii | 0.89 | 1.8 | 2.687(7) | 172.2 |
N2-H2C…O1 iii | 0.89 | 1.93 | 2.811(6) | 172.8 |
N2-H2D…O2 iv | 0.89 | 1.91 | 2.800(6) | 174.2 |
N2-H2E…O2 i | 0.89 | 2.13 | 2.976(6) | 157.8 |
O5-H5C…O2 v | 0.85 | 1.91 | 2.745(6) | 168.1 |
O5-H5D…O3 v | 0.85 | 1.99 | 2.798(5) | 158.5 |
O6-H6C…O5 | 0.85 | 2.06 | 2.863 | 157.2 |
O6-H6D…O3 i | 0.85 | 2.07 | 2.867(6) | 156.4 |
D-H…A | d(D-H)/Å | d(H-A)/Å | d(D-A)/Å | D-H-A/° |
---|---|---|---|---|
N1-H1A…O3 i | 0.89 | 1.91 | 2.773(3) | 161.5 |
N1-H1B…O2 ii | 0.89 | 1.92 | 2.806(2) | 175.9 |
N1-H1C…O4 iii | 0.89 | 1.82 | 2.705(3) | 174.6 |
N2-H2C…O2 iii | 0.89 | 1.94 | 2.824(3) | 170.3 |
N2-H2D…O1 iv | 0.89 | 1.93 | 2.813(2) | 169.2 |
O5-H5C…O1 v | 0.85 | 1.93 | 2.773(2) | 172.4 |
O5-H5D…O3 v | 0.85 | 1.99 | 2.823(2) | 166.4 |
O6-H6C…O3 v | 0.85 | 2.05 | 2.891(3) | 168.5 |
O6-H6D…O5 vi | 0.85 | 2.09 | 2.872(3) | 152.6 |
N | Symop | R | E_ele | E_pol | E_dis | E_rep | E_tot |
---|---|---|---|---|---|---|---|
1 | x, y, z | 8.43 | 1.5 | −0.1 | −1.6 | 0 | 0 |
1 | −x, −y, −z | 18.75 | 0 | −0.3 | 0 | 0 | −0.2 |
1 | −x, −y, −z | 19.01 | 0 | −0.0 | 0 | 0 | −0.0 |
2 | x, y, z | 6.65 | −0.6 | −1.1 | −31.1 | 10.6 | −20.8 |
1 | −x, −y, −z | 17.29 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | x, y, z | 13.3 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | −x, −y, −z | 18.03 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 6.83 | 0 | 0 | 0 | 0 | 0 |
1 | - | 10.66 | −0.6 | −1.1 | −31.1 | 10.6 | −20.8 |
1 | - | 10.45 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 20.71 | 0 | 0 | 0 | 0 | 0 |
1 | - | 7.64 | −0.6 | −1.1 | −31.1 | 10.6 | −20.8 |
1 | - | 18.77 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 5.99 | 1 | −0.1 | −1.9 | 0 | −0.8 |
1 | - | 20.25 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 11.86 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 20.21 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 12.63 | 1.5 | −0.1 | −1.6 | 0 | 0 |
1 | - | 11.37 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 10.78 | 0 | 0 | 0 | 0 | 0 |
1 | - | 8.96 | 0 | 0 | 0 | 0 | 0 |
1 | x, y, z | 10.09 | 1 | −0.1 | −1.9 | 0 | −0.8 |
1 | −x, −y, −z | 17.41 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | −x, −y, −z | 20.96 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 8.53 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 12.56 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 9.32 | −0.6 | −1.1 | −31.1 | 10.6 | −20.8 |
1 | - | 19.08 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 4.41 | 1.5 | −0.1 | −1.6 | 0 | 0 |
1 | - | 22.25 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 11.36 | 0.6 | −0.0 | −0.3 | 0 | 0.3 |
1 | - | 11.9 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 7.35 | −0.6 | −1.1 | −31.1 | 10.6 | −20.8 |
1 | - | 10.73 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 10.02 | −0.6 | −1.1 | −31.1 | 10.6 | −20.8 |
1 | - | 8.56 | 0 | −0.0 | 0 | 0 | −0.0 |
N | Symop | R | E_ele | E_pol | E_dis | E_rep | E_tot |
---|---|---|---|---|---|---|---|
1 | x, y, z | 8.49 | 1.5 | −0.1 | −1.7 | 0 | −0.1 |
1 | −x, −y, −z | 20.08 | 0 | −0.3 | 0 | 0 | −0.2 |
1 | −x, −y, −z | 20.18 | 0 | −0.0 | 0 | 0 | −0.0 |
2 | x, y, z | 6.69 | −0.4 | −1.1 | −31.1 | 9.5 | −21.4 |
1 | −x, −y, −z | 18.24 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | x, y, z | 13.39 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | −x, −y, −z | 18.66 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 7.38 | 0 | 0 | 0 | 0 | 0 |
1 | - | 11.08 | −0.4 | −1.1 | −31.1 | 9.5 | −21.4 |
1 | - | 11.1 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 22.01 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 7.7 | −0.4 | −1.1 | −31.1 | 9.5 | −21.4 |
1 | - | 19.89 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 5.99 | 1 | −0.1 | −2.0 | 0 | −0.9 |
1 | - | 21.16 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 13.39 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 19.91 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 11.91 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 20.85 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 13.34 | 1.5 | −0.1 | −1.7 | 0 | −0.1 |
1 | - | 11.62 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 11.33 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 11.2 | 0 | 0 | 0 | 0 | 0 |
1 | x, y, z | 10.15 | 1 | −0.1 | −2.0 | 0 | −0.9 |
1 | −x, −y, −z | 18.52 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | −x, −y, −z | 21.28 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 8.69 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 12.73 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 9.4 | −0.4 | −1.1 | −31.1 | 9.5 | −21.4 |
1 | - | 4.42 | 1.5 | −0.1 | −1.7 | 0 | −0.1 |
1 | - | 22.06 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 22.61 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 11.9 | 0.6 | −0.0 | −0.3 | 0 | 0.3 |
1 | - | 11.92 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 7.71 | −0.4 | −1.1 | −31.1 | 9.5 | −21.4 |
1 | - | 11.02 | 0 | −0.0 | 0 | 0 | −0.0 |
1 | - | 8.76 | −0.4 | −1.1 | −31.1 | 9.5 | −21.4 |
1 | - | 10.42 | 0 | −0.0 | 0 | 0 | −0.0 |
Descriptors | 3C16, Values (eV) | 3C17, Values (eV) |
---|---|---|
ELUMO | −2.6476 | −2.7088 |
EHOMO | −2.9334 | −2.9943 |
Energy gap (∆E) | 0.2858 | 0.2855 |
Ionization energy (I) | 2.9334 | 2.9943 |
Electron affinity (A) | 2.6476 | 2.7088 |
Electronegativity (χ) | 2.7905 | 2.8516 |
Chemical potential (μ) | −2.7905 | −2.8516 |
Global hardness (η) | 0.1429 | 0.1428 |
Global softness (σ) | 3.4990 | 3.5014 |
Electrophilicity index (ω) | 27.2459 | 28.4821 |
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Ke, Z.; Fan, X.; Di, Y.; Chen, F.; Han, X.; Yang, K.; Li, B. A Comprehensive Investigation into the Crystallology, Molecule, and Quantum Chemistry Properties of Two New Hydrous Long-Chain Dibasic Ammonium Salts CnH2n+8N2O6 (n = 35 and 37). Int. J. Mol. Sci. 2023, 24, 5467. https://doi.org/10.3390/ijms24065467
Ke Z, Fan X, Di Y, Chen F, Han X, Yang K, Li B. A Comprehensive Investigation into the Crystallology, Molecule, and Quantum Chemistry Properties of Two New Hydrous Long-Chain Dibasic Ammonium Salts CnH2n+8N2O6 (n = 35 and 37). International Journal of Molecular Sciences. 2023; 24(6):5467. https://doi.org/10.3390/ijms24065467
Chicago/Turabian StyleKe, Zengbo, Xinhui Fan, Youying Di, Fengying Chen, Xi Han, Ke Yang, and Bing Li. 2023. "A Comprehensive Investigation into the Crystallology, Molecule, and Quantum Chemistry Properties of Two New Hydrous Long-Chain Dibasic Ammonium Salts CnH2n+8N2O6 (n = 35 and 37)" International Journal of Molecular Sciences 24, no. 6: 5467. https://doi.org/10.3390/ijms24065467