Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid
Abstract
:1. Introduction
2. Experimental Setup
2.1. Materials and Methods
2.2. Synthesis and Crystallization of H2Br4tp·2MeCN (1MeCN)
2.3. Synthesis and Crystallization of H2Br4tp·2MeOH (2MeOH)
2.4. X-ray Crystallography
3. Results and Discussion
3.1. Structural Description
3.2. Hirshfeld Surface Analysis
3.3. Thermal Analysis and Structural Transformation
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | H2Br4tp·2MeCN (1MeCN) | H2Br4tp·2MeOH (2MeOH) |
---|---|---|
Empirical formula | C12H8Br4N2O4 | C10H10Br4O6 |
Formula weight | 563.84 | 545.82 |
Temperature (K) | 296(2) | 296(2) |
Crystal system | Triclinic | Monoclinic |
Space group | P-1 | P21/c |
a (Å) | 6.1577(6) | 11.8461(11) |
b (Å) | 8.3463(8) | 9.2213(8) |
c (Å) | 9.2327(9) | 15.1000(14) |
α (°) | 68.241(3) | 90 |
β (°) | 78.863(4) | 107.840(3) |
γ (°) | 84.436(4) | 90 |
V (Å3) | 432.23(7) | 1570.2(2) |
Z | 1 | 4 |
ρcalc (g/cm3) | 2.166 | 2.309 |
µ (mm−1) | 9.327 | 10.271 |
F(000) | 266 | 1032 |
λ (Å) | 0.71073 (Mo-Kα) | 0.71073 (Mo-Kα) |
θ range (°) | 3.4–32.1 | 2.8–32.1 |
Reflections collected | 17952 | 50246 |
Independent reflections | 3149 | 5490 |
Rint, Rsigma | 0.0566, 0.0429 | 0.0968, 0.0650 |
Data/restraints/parameters | 3149/1/106 | 5490/4/200 |
Goodness-of-fit on F2 | 1.028 | 1.025 |
R1, wR2 [I > 2σ(I)] | 0.0427, 0.0731 | 0.0519, 0.0944 |
R1, wR2 [all data] | 0.0909, 0.0871 | 0.1189, 0.1167 |
Δρmax, Δρmin (e Å−3) | 0.57, −0.69 | 0.93, −1.14 |
CCDC number | 2005667 | 2005668 |
C−Br···X | d(Br···X) (Å) | ∠(C−Br···X) (°) | Symmetry Code |
---|---|---|---|
1MeCN | |||
C3–Br1···Br2 | 3.9434(7) | 85.26(10) | −x, −y, 1 − z |
C4–Br2···O2 | 3.270(3) | 155.24(11) | x, y, z − 1 |
2MeOH | |||
C3–Br1···O4 | 3.087(4) | 173.41(14) | 1 − x, 1/2 + y, 3/2 − z |
C4–Br2···O1 | 3.043(3) | 177.69(15) | 1 − x, 1/2 + y, 3/2 − z |
C4–Br2···Br3 | 3.7233(7) | 89.77(13) | x, 1/2 − y, z + 1/2 |
C4–Br2···Br4 | 3.8507(8) | 119.49(13) | x, 1/2 − y, z + 1/2 |
C8–Br3···Br1 | 3.7989(7) | 176.35(13) | x, 1/2 − y, z − 1/2 |
C8–Br3···Br3 | 3.7994(11) | 77.52(13) | 1 − x, −y, 1 − z |
C8–Br3···Br4 | 3.8871(8) | 103.15(13) | 1 − x, −y, 1 − z |
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Chongboriboon, N.; Samakun, K.; Dungkaew, W.; Kielar, F.; Sukwattanasinitt, M.; Chainok, K. Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid. Crystals 2021, 11, 198. https://doi.org/10.3390/cryst11020198
Chongboriboon N, Samakun K, Dungkaew W, Kielar F, Sukwattanasinitt M, Chainok K. Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid. Crystals. 2021; 11(2):198. https://doi.org/10.3390/cryst11020198
Chicago/Turabian StyleChongboriboon, Nucharee, Kodchakorn Samakun, Winya Dungkaew, Filip Kielar, Mongkol Sukwattanasinitt, and Kittipong Chainok. 2021. "Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid" Crystals 11, no. 2: 198. https://doi.org/10.3390/cryst11020198