Cocrystals Based on 4,4’-bipyridine: Influence of Crystal Packing on Melting Point
Abstract
:1. Introduction
2. Experimental Section
2.1. Materials and General Methods
2.2. Synthesis of Cocrystals 1 and 2
2.3. X-ray Crystallographic Data
2.4. Computational Details of Hirshfeld Surface Analysis, Energy Frameworks, and Lattice Energy
3. Results and Discussion
3.1. Synthesis and Characterization of Cocrystals 1 and 2
3.2. Crystal and Extended Structure of (HPip)(4,4’-bipy) (1)
3.3. Crystal and Extended Structure of (HCinn)2(4,4’-bipy) (2)
3.4. Hirshfeld Surface Analysis and Energy Frameworks Calculations of 1 and 2
3.5. Relationship of Melting Point Values with Packing Effects of Cocrystals 1 and 2
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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1 | 2 | |
---|---|---|
CCDC | 2058460 | 2058461 |
Empirical Formula | C18H14N2O4 | C28H24N2O4 |
Formula weight | 322.31 | 452.49 |
T (K) | 100(2) | 100(2) |
Wavelength (Å) | 0.71073 | 0.71073 |
System, space group | Monoclinic, P21/c | Monoclinic, P21/n |
a (Å) | 3.7524(6) | 7.8058(10) |
b (Å) | 18.427(3) | 7.1639(8) |
c (Å) | 21.139(3) | 20.786(3) |
α (°) | 90 | 90 |
β (°) | 92.646(6) | 93.147(5) |
γ (°) | 90 | 90 |
V (Å3) | 1460.1(4) | 1160.6(3) |
Z | 4 | 2 |
Dcalc (mg/m3) | 1.466 | 1.295 |
µ (mm−1) | 0.105 | 0.087 |
F (000) | 672 | 476 |
Crystal size (mm3) | ||
hkl ranges | −4<=h<=4, −23<=k<=23, −26<=l<=26 | −11<=h<=11, −10<=k<=10, −29<=l<=29 |
θ range (°) | 2.210 to 26.402 | 2.741 to 30.909 |
Reflections collected/unique/[Rint] | 20300 / 2999 / [Rint] = 0.0640 | 18015 / 3609 / [Rint] = 0.0778 |
Completeness to θ (%) | 99.8 | 99.9 |
Absorption correction | Semi-empirical from equivalents | Semi-empirical from equivalents |
Max. and min. transmission | 0.7474 and 0.6133 | 0.7461 and 0.6585 |
Refinement method | Full-matrix least-squares on 2 | Full-matrix least-squares on 2 |
Data/Restrains/Parameters | 2999 / 0 / 221 | 3609 / 0 / 157 |
Goodness-on-fit (GOF) on 2 | 1.107 | 1.063 |
Final R indices [I>2σ(I)] | R1 = 0.0539 wR2 = 0.1113 | R1 = 0.0553 wR2 = 0.1108 |
R indices (all data) | R1 = 0.0692 wR2 = 0.1174 | R1 = 0.1229 wR2 = 0.1507 |
Extinction coefficient | n/a | 0.019(3) |
Largest diff-peak and hole (e. Å−3) | 0.232 and −0.290 | 0.301 and −0.297 |
D-H···A | D-H (Å) | H···A (Å) | D···A (Å) | > D-H···A (°) | |
O(1)-H(1)···N(1) | 0.99(3) | 1.62(4) | 2.603(2) | 172(3) | |
C(13)-H(13)···O(2) | 0.95 | 2.95 | 3.540(3) | 121 | |
C(4)-H(4)···O(3) | 0.95 | 2.69 | 3.612(2) | 164 | |
C(6)-H(6AB)···N(2) | 0.99 | 2.58 | 3.348(3) | 134 | |
C(12)-H(12)···O(2) | 0.95 | 2.47 | 3.369(3) | 159 | |
C(15)-H(15)···O(2) | 0.95 | 2.45 | 3.395(3) | 173 | |
C(10)-H(10)···O(4) | 0.95 | 2.47 | 3.326(3) | 150 | |
C(6)-H(6A)···N(2) | 0.99 | 2.73 | 3.589(3) | 146 | |
Cg(I)···Cg(J) | dCg-Cga (Å) | αb (°) | β, γc (°) | dplane-planed | doffsete |
Cg(1)···Cg(1) | 3.7523(13) | 0 | 28.4 | 3.3021(8) | 1.782 |
Cg(2)···Cg(2) | 3.7524(14) | 0 | 20.3 | 3.5187(9) | 1.304 |
Cg(3)···Cg(3) | 3.7523(13) | 0 | 20.6 | 3.5113(9) | 1.323 |
D-H···A | D-H (Å) | H···A (Å) | D···A (Å) | > D-H···A (°) |
---|---|---|---|---|
O(1)-H(f··N(003) | 1.03(2) | 1.61(2) | 2.636(2) | 178.4(14) |
C(10)-H(10)···O2 | 0.95 | 2.57 | 3.227(2) | 126 |
C(2)-H(2)···O(2) | 0.95 | 2.47 | 3.381(2) | 160 |
C(9)-H(9)···O(1) | 0.95 | 2.68 | 3.401(2) | 133 |
C(7)-H(7)···Cg(1) | 0.95 | 2.95 | 3.770(2) | 146 |
Structure | CCDC Number | Elat (KJ/mol) |
---|---|---|
4,4’-bipy | 131130 [56] | −93.8 |
HPip | 608427 [57] | −121.2 |
HCinn | 1547787 [58] | −115.6 |
1 | 2058460 | −225.4 |
2 | 2058461 | −333.7 |
Structure | CCDC Number | Melting Point (°C) | Crystal Density (mg/m3) | Packing Efficiency (%) |
---|---|---|---|---|
4,4’-bipy | 131130 [56] | 112–113 | 1.255 | 68.00 |
HPip | 608427 [57] | 231–232 | 1.555 | 72.63 |
HCinn | 1547787 [58] | 135–136 | 1.321 | 70.96 |
1 | 2058460 | 188–189 | 1.466 | 73.79 |
2 | 2058461 | 110–111 | 1.295 | 69.63 |
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Ejarque, D.; Calvet, T.; Font-Bardia, M.; Pons, J. Cocrystals Based on 4,4’-bipyridine: Influence of Crystal Packing on Melting Point. Crystals 2021, 11, 191. https://doi.org/10.3390/cryst11020191
Ejarque D, Calvet T, Font-Bardia M, Pons J. Cocrystals Based on 4,4’-bipyridine: Influence of Crystal Packing on Melting Point. Crystals. 2021; 11(2):191. https://doi.org/10.3390/cryst11020191
Chicago/Turabian StyleEjarque, Daniel, Teresa Calvet, Mercè Font-Bardia, and Josefina Pons. 2021. "Cocrystals Based on 4,4’-bipyridine: Influence of Crystal Packing on Melting Point" Crystals 11, no. 2: 191. https://doi.org/10.3390/cryst11020191