Figure . The molecular diagram of Carbamazepine.
| REFCODE | CBMZPN |
|---|---|
| Formula | C15 H12 N2 O1 |
| Common Name | Carbamazepine |
| IUPAC Systematic Name | 5-carbamoyl-5H-dibenz[b,f]azepine |
| Other Names | 5H-Dibenz[b,f]azepine-5-carboxamide; Carbamazepine; Carbamezapine; Carbazepine; Epitol; Tegertol; Tegretol; Teril |
| CSD Refcodes | CBMZPN11; CBMZPN03; CBMZPN10; CBMZPN12; CBMZPB16 |
| Search Identifier | A |
| Scientist | Rui Guo |
| Date | 2016 |
| Publication | Unpublished |
| Energy model | 2 |
| Study_ID | 30 |
| Programs | Study_ID=12, DMACRYS (2.2.0.1) |
| Location on S Drive | CHEMISTRY_CPOSS\\CarbamazepineSeries\\Carbamazepine_PCM |
| Potential Description | GDMA2.2(PCMdielectric3(PBE0/6-31+G(d))) + FIT |
| Energy model | 1 |
| Study_ID | 12 (includes pDFT-D) |
| Programs | CrystalPredictor (2.1.01), CrystalOptimizer (2.4.m), DMACRYS (2.2.0.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\CarbamazepineSeries\\Carbamazepine_CO |
| Potential Description | CrystalOptimizer with PBE0/6-31G(d,p) Intra and GDMA2.2(PBE0/6-31G(d,p)) + FIT |
| Search Identifier | B |
| Scientist | Harriott Nowell, Panos Karamertzanis |
| Date | 2005 |
| Publication | Florence AJ; Johnston A; Price SL; Nowell H; Kennedy AR; Shankland N, J. Pharm. Sci., 95(9), 1918-1930 (2006) DOI: Open paper (10.1002/jps.20647) |
| Energy Model | 2 |
| Study_ID | 10 |
| Programs | Study_ID=0, dmaflex, DMAREL (4.1.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\carbamazepine_dmaflex |
| Potential Description | DMA + FIT SCF model, with DMAflex |
| Energy Model | 1 |
| Study_ID | 0 |
| Programs | MOLPAK, DMAREL (4.1.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\carbamazepine |
| Potential Description | DMA + FIT |
Figure . (Top) crystal energy landscape of Carbamazepine from Study_ID=12. (Bottom left) crystal energy landscape of Carbamazepine from Study_ID=30. (Bottom right) relative energies by method of key structures.
Table . Crystallographic information for CSD entries for Carbamazepine. Different polymorphs are coloured differently.
| REFCODE | space group | Z’ | a / Å | b / Å | c / Å | α / ° | β / ° | γ / ° | density / g cm-3 | Form |
|---|---|---|---|---|---|---|---|---|---|---|
| CBMZPN | P21/n | 1 | 7.537 | 11.156 | 13.912 | 90 | 92.86 | 90 | 1.343 | III |
| CBMZPN01 | P21/c | 1 | 7.529 | 11.148 | 15.47 | 90 | 116.17 | 90 | 1.347 | III |
| CBMZPN02 | P21/n | 1 | 7.534 | 11.15 | 13.917 | 90 | 92.94 | 90 | 1.344 | III |
| CBMZPN03 | R-3 | 1 | 35.454 | 35.454 | 5.253 | 90 | 90 | 120 | 1.235 | II |
| CBMZPN10 | P21/n | 1 | 7.537 | 11.156 | 13.912 | 90 | 92.86 | 90 | 1.343 | III |
| CBMZPN11 | P-1 | 4 | 5.1705 | 20.574 | 22.245 | 84.124 | 88.008 | 85.187 | 1.339 | I |
| CBMZPN12 | C2/c | 1 | 26.609 | 6.9269 | 13.957 | 90 | 109.702 | 90 | 1.296 | IV |
| CBMZPN13 | P-1 | 4 | 5.1856 | 20.5758 | 22.2411 | 84.1942 | 87.9756 | 85.1053 | 1.335 | I |
| CBMZPN14 | P21/n | 1 | 7.55 | 11.186 | 13.954 | 90 | 92.938 | 90 | 1.333 | III |
| CBMZPN15 | P21/n | 1 | 7.53 | 11.19 | 13.96 | 90 | 93.03 | 90 | 1.336 | III |
| CBMZPN16 | Pbca | 1 | 9.1245 | 10.4518 | 24.8224 | 90 | 90 | 90 | 1.326 | V |
| CBMZPN17 | P21/n | 1 | 7.4874 | 11.0406 | 13.7754 | 90 | 92.939 | 90 | 1.38 | III |
| CBMZPN18 | P21/n | 1 | 7.4874 | 11.0406 | 13.7754 | 90 | 92.939 | 90 | 0 | III |
| CBMZPN19 | P21/n | 1 | 7.487 | 11.041 | 13.775 | 90 | 92.9 | 90 | 1.38 | III |
| CBMZPN20 | P21 | 2 | 7.542 | 11.155 | 13.919 | 90 | 92.885 | 90 | 1.342 | III |
| CBMZPN21 | P21/n | 1 | 7.498 | 11.058 | 13.789 | 90 | 92.838 | 90 | 1.374 | III |
| CBMZPN22 | P21/n | 1 | 7.4893 | 11.0323 | 13.764 | 90 | 92.953 | 90 | 1.382 | III |
| CBMZPN23 | P21/n | 1 | 7.4893 | 11.0323 | 13.764 | 90 | 92.953 | 90 | 1.382 | III |
| CBMZPN27 | P21/n | 1 | 7.49441 | 11.0643 | 13.8036 | 90 | 92.9142 | 90 | 1.373 | III |
| CBMZPN28 | P21/n | 1 | 7.578 | 11.176 | 13.991 | 90 | 93.08 | 90 | 1.326 | III |
| CBMZPN29 | P21/n | 1 | 7.576 | 11.188 | 13.967 | 90 | 87.03 | 90 | 1.327 | III |
| CBMZPN30 | P21/n | 1 | 7.68 | 11.44 | 13.92 | 90 | 91.22 | 90 | 1.283 | III |
| CBMZPN31 | P21/n | 1 | 7.46 | 11.04 | 13.76 | 90 | 92.61 | 90 | 1.386 | III |
| CBMZPN32 | P21/n | 1 | 7.534 | 11.15 | 13.917 | 90 | 92.94 | 90 | 1.344 | III |
| CBMZPN33 | P21/n | 1 | 7.4907 | 11.058 | 13.7853 | 90 | 92.903 | 90 | 1.376 | III |
| CBMZPN34 | P21/n | 1 | 7.614 | 11.302 | 13.886 | 90 | 92.43 | 90 | 1.314 | III |
| CBMZPN35 | C2/c | 1 | 27.15 | 7.3 | 14.1 | 90 | 110.3 | 90 | 1.198 | IV |
| CBMZPN36 | P21/n | 1 | 7.46 | 11.04 | 13.76 | 90 | 92.61 | 90 | 1.386 | III |
| CBMZPN37 | P21/n | 1 | 7.547 | 11.158 | 13.92 | 90 | 92.87 | 90 | 1.34 | III |
Table . Experimental information for CSD entries for Carbamazepine.
| REFCODE | space group | R factor | T / K | Year | Comments |
|---|---|---|---|---|---|
| CBMZPN | P21/n | 4 | 295 | 1981 | |
| CBMZPN01 | P21/c | 3.5 | 295 | 1981 | Recrystallization from ethanol1 |
| CBMZPN02 | P21/n | 8.4 | 295 | 1989 | Recrystallization from ethanol2 |
| CBMZPN03 | R-3 | 6.9 | 295 | 1987 | Slow evaporation from THF, CHF3 and CCl43 |
| CBMZPN10 | P21/n | 3.9 | 295 | 1981 | Recrystallization from ethanol4 |
| CBMZPN11 | P-1 | 5.06 | 158 | 2003 | Crystallized from the melt in a sealed capillary5 |
| CBMZPN12 | C2/c | 3.57 | 158 | 2002 | Crystallization in the presence of hydroxypropylcellulose6 |
| CBMZPN13 | P-1 | 17.96 | 160 | 2007 | Heating form III to above 165 °C7 |
| CBMZPN14 | P21/n | 4.04 | 300 | 2011 | Not reported8 |
| CBMZPN15 | P21/n | 0 | 295 | 2008 | Crystallized from a 5-component system9 |
| CBMZPN16 | Pbca | 4.5 | 123 | 2011 | Sublimation onto template10 |
| CBMZPN17 | P21/n | 3.06 | 293 | 2013 | Slow evaporation of supersaturated solution of methanol11 |
| CBMZPN18 | P21/n | 1.08 | 100 | 2013 | Slow evaporation of supersaturated solution of methanol11 |
| CBMZPN19 | P21/n | 0 | 0 | 2013 | Slow evaporation of supersaturated solution of methanol11 |
| CBMZPN20 | P21 | 3.95 | 298 | 2015 | Elaborate crystallization protocol using chips and microfluidic assemblies and coformers12 |
| CBMZPN21 | P21/n | 6.79 | 100 | 2016 | Not specified13 |
| CBMZPN22 | P21/n | 4.07 | 100 | 2016 | Not specified13 |
| CBMZPN23 | P21/n | 2.4 | 100 | 2016 | Not specified13 |
| CBMZPN27 | P21/n | 4.26 | 183 | 2017 | Thermal crystallization on a multireactor crystallization platform14 |
| CBMZPN28 | P21/n | 25.45 | 293 | 2016 | Crushing dry crystals and rubbing them between two microscope slides15 |
| CBMZPN29 | P21/n | 40.54 | 293 | 2016 | Crushing dry crystals and rubbing them between two microscope slides15 |
| CBMZPN30 | P21/n | 36.9 | 293 | 2016 | Crushing dry crystals and rubbing them between two microscope slides15 |
| CBMZPN31 | P21/n | 19.21 | 293 | 2018 | Not specified16 |
| CBMZPN32 | P21/n | 43.85 | 293 | 2019 | Not specified17 |
| CBMZPN33 | P21/n | 5.01 | 150 | 2018 | Slow evaporation from ethanol18 |
| CBMZPN34 | P21/n | 19.68 | 100 | 2021 | Pressure-assisted blotting of an ethanol solution19 |
| CBMZPN35 | C2/c | 19.86 | 100 | 2021 | Pressure-assisted blotting of an ethanol solution19 |
| CBMZPN36 | P21/n | 19.21 | 293 | 2020 | See CBMZPN3116 |
| CBMZPN37 | P21/n | 4.04 | 293 | 2022 | Private communication |
Make this table include whether polymorphs are solution-grown, sublimation grown, templated or otherwise. Add references.
There is also a 1:1 solid solution of Carbamazepine and Dihydrocarbamazepine.20
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3. M. M. J. Lowes, M. R. Caira, A. P. Lotter and J. G. Vanderwatt, Journal of Pharmaceutical Sciences, 1987, 76, 744-752.
4. V. L. Himes, A. D. Mighell and W. H. DeCamp, Acta Crystallographica Section B - Structural Crystallography and Crystal Chemistry, 1981, 37, 2242-2245.
5. A. L. Grzesiak, M. D. Lang, K. Kim and A. J. Matzger, Journal of Pharmaceutical Sciences, 2003, 92, 2260-2271.
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8. K. S. Eccles, S. P. Stokes, C. A. Daly, N. M. Barry, S. P. McSweeney, D. J. O'Neill, D. M. Kelly, W. B. Jennings, O. M. Ni Dhubhghaill, H. A. Moynihan, A. R. Maguire and S. E. Lawrence, Journal of Applied Crystallography, 2011, 44, 213-215.
9. A. Kogan, I. Popov, V. Uvarov, S. Cohen, A. Aserin and N. Garti, Langmuir, 2008, 24, 722-733.
10. J. B. Arlin, L. S. Price, S. L. Price and A. J. Florence, Chemical Communications, 2011, 47, 7074-7076.
11. N. El Hassan, A. Ikni, J. M. Gillet, A. Spasojevic-de Bire and N. E. Ghermani, Crystal Growth & Design, 2013, 13, 2887-2896.
12. E. M. Horstman, S. Goyal, A. Pawate, G. Lee, G. G. Z. Zhang, Y. Gong and P. J. A. Kenis, Crystal Growth & Design, 2015, 15, 1201-1209.
13. I. Sovago, M. J. Gutmann, H. M. Senn, L. H. Thomas, C. C. Wilson and L. J. Farrugia, Acta Crystallographica Section B-Structural Science Crystal Engineering and Materials, 2016, 72, 39-50.
14. P. P. Nievergelt and B. Spingler, CrystEngComm, 2017, 19, 142-147.
15. E. van Genderen, M. T. B. Clabbers, P. P. Das, A. Stewart, I. Nederlof, K. C. Barentsen, Q. Portillo, N. S. Pannu, S. Nicolopoulos, T. Gruene and J. P. Abrahams, Acta Crystallographica Section A, 2016, 72, 236-242.
16. C. G. Jones, M. W. Martynowycz, J. Hattne, T. J. Fulton, B. M. Stoltz, J. A. Rodriguez, H. M. Nelson and T. Gonen, ACS Central Science, 2018, 4, 1587-1592.
17. U. Kolb, Y. Krysiak and S. Plana-Ruiz, Acta Crystallographica Section B, 2019, 75, 463-474.
18. J. J. Du, S. A. Stanton, S. Fakih, B. A. Hawkins, P. A. Williams, P. W. Groundwater, J. Overgaard, J. A. Platts and D. E. Hibbs, Crystal Growth & Design, 2021, 21, 4259-4275.
19. E. T. Broadhurst, H. Xu, S. Parsons and F. Nudelman, IUCrJ, 2021, 8, 860-866.
20. A. J. Florence, C. K. Leech, N. Shankland, K. Shankland and A. Johnston, CrystEngComm, 2006, 8, 746-747.