(Last updated January 2026)
Figure . The molecular diagram of Ibuprofen.
| REFCODE | IBPRAC |
|---|---|
| Formula | C13 H18 O2 |
| Common Name | Ibuprofen |
| IUPAC Systematic Name | 2-[4-(2-methylpropyl)phenyl]propanoic acid |
| Other Names | Advil, Motrin, Nurofen |
| CSD Refcodes | IBPRAC01, IBPRAC04, JEKNOC12 |
| Search Identifier | A |
| Scientist | Louise Price |
| Date | 2019 |
| Publication | Francia NF, Price LS, Salvalaglio M, CrystEngComm 2021. 23, 5575-5584. DOI: Open paper (10.1039/d1ce00616a) |
| Energy model | 3 |
| Study_ID | 11 |
| Programs | Study_ID=60, CrystalOptimizer, DMACRYS (2.3.0) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\MagnaPharm\\Ibuprofen\\DFTB3_CrystOpt |
| Potential Description | CrystalOptimizer with GDMA2.2(PBE1PBE/aug-cc-pVDZ) + PBE1PBE 6-31G(d,p) DEintra + FIT |
| Intramolecular Description | PBE1PBE/6-31G(d,p) |
| Energy model | 2 |
| Study_ID | 60 |
| Programs | Study_ID=20, DFTB3D3, DMACRYS (2.3.0) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\MagnaPharm\\Ibuprofen\\DFTB3 |
| Potential Description | CrystalPredictor, followed by DFTB3-D3 refinement, followed by DMACRYS with GDMA2.2(PBE0/aug-cc-pVDZ) + FIT |
| Intramolecular Description | PPBE0/aug-cc-pVDZ |
| Energy model | 4 |
| Study_ID | 10 |
| Programs | Study_ID=20, CrystalOptimizer (2.4.7), DMACRYS (2.2.1.0) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\MagnaPharm\\Ibuprofen\\CrystOpt |
| Potential Description | CrystalOptimizer with GDMA2.2(PBE1PBE/6-31G(d,p) + FIT |
| Intramolecular Description | PBE1PBE/6-31G(d,p) |
| Energy model | 1 |
| Study_ID | 20 |
| Programs | Flexible CrystalPredictor (1.9 with torsion groups), DMACRYS (2.2.1.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\MagnaPharm\\Ibuprofen\\CrystalPredictor |
| Potential Description | POTENTIAL_DESCRIPTION |
| Intramolecular Description | PBE1PBE/6-31G(d,p) |
Figure . Crystal energy landscape of Ibuprofen from previous work. Top: Following DFTB3D3 and CrystalOptimizer (as published, energy model 3). Bottom left: Following CrystalOptimizer directly from Crystal Predictor. Bottom right: Energy comparisons including DFT+D.
The structure that matches Form 2 in the search is a Z’=2 structure in P-1.
Table . Crystallographic information for CSD entries for Ibuprofen. Different polymorphs are coloured differently.
| REFCODE | space group | Z’ | a / Å | b / Å | c / Å | α / ° | β / ° | γ / ° | density / g cm-3 | Form |
|---|---|---|---|---|---|---|---|---|---|---|
| IBPRAC | P21/c | 1 | 14.667 | 7.886 | 10.73 | 90 | 99.362 | 90 | 1.119 | 1 |
| IBPRAC01 | P21/c | 1 | 14.397 | 7.818 | 10.506 | 90 | 99.7 | 90 | 1.176 | 1 |
| IBPRAC02 | P21/c | 1 | 14.397 | 7.818 | 10.506 | 90 | 99.7 | 90 | 1.176 | 1 |
| IBPRAC03 | P21/c | 1 | 14.6712 | 7.8893 | 10.7288 | 90 | 99.428 | 90 | 1.118 | 1 |
| IBPRAC04 | P21/c | 1 | 12.3794 | 5.8723 | 17.5615 | 90 | 94.873 | 90 | 1.077 | 2 |
| IBPRAC05 | P21/c | 1 | 14.522 | 7.817 | 10.619 | 90 | 99.54 | 90 | 1.153 | 1 |
| IBPRAC06 | P21/c | 1 | 14.6737 | 7.895 | 10.7345 | 90 | 99.541 | 90 | 1.117 | 1 |
| IBPRAC07 | P21/c | 1 | 14.309 | 7.686 | 10.47 | 90 | 99.85 | 90 | 1.208 | 1 |
| IBPRAC08 | P21/c | 1 | 14.205 | 7.6697 | 10.318 | 90 | 100.09 | 90 | 1.238 | 1 |
| IBPRAC09 | P21/c | 1 | 14.196 | 7.638 | 10.32 | 90 | 100.13 | 90 | 1.244 | 1 |
| IBPRAC10 | P21/c | 1 | 13.977 | 7.536 | 10.12 | 90 | 100.3 | 90 | 1.306 | 1 |
| IBPRAC11 | P21/c | 1 | 13.9958 | 7.514 | 10.067 | 90 | 100.41 | 90 | 1.316 | 1 |
| IBPRAC12 | P21/c | 1 | 13.905 | 7.4574 | 10.007 | 90 | 100.21 | 90 | 1.342 | 1 |
| IBPRAC13 | P21/c | 1 | 13.865 | 7.4064 | 9.977 | 90 | 100.27 | 90 | 1.359 | 1 |
| IBPRAC14 | P21/c | 1 | 13.779 | 7.324 | 9.844 | 90 | 100.28 | 90 | 1.402 | 1 |
| IBPRAC15 | P21/c | 1 | 13.7397 | 7.2685 | 9.804 | 90 | 100.195 | 90 | 1.422 | 1 |
| IBPRAC16 | P21/c | 1 | 14.4847 | 7.8321 | 10.4907 | 90 | 99.743 | 90 | 1.168 | 1 |
| IBPRAC17 | P21/c | 1 | 14.5144 | 7.8429 | 10.5297 | 90 | 99.609 | 90 | 1.159 | 1 |
| IBPRAC18 | P21/c | 1 | 14.5609 | 7.857 | 10.5867 | 90 | 99.563 | 90 | 1.147 | 1 |
| IBPRAC19 | P21/c | 1 | 14.605 | 7.8721 | 10.6507 | 90 | 99.525 | 90 | 1.135 | 1 |
| IBPRAC20 | P21/c | 1 | 14.65 | 7.88 | 10.73 | 90 | 99.7 | 90 | 1.122 | 1 |
| IBPRAC21 | P21/c | 1 | 14.465 | 7.815 | 10.435 | 90 | 99.66 | 90 | 1.178 | 1 |
| IBPRAC22 | P21/c | 1 | 14.65 | 7.88 | 10.73 | 90 | 99.7 | 90 | 1.122 | 1 |
| JEKNOC | P21 | 2 | 12.462 | 8.035 | 13.539 | 90 | 112.89 | 90 | 1.097 | |
| JEKNOC10 | P21 | 2 | 12.462 | 8.035 | 13.539 | 90 | 112.89 | 90 | 1.097 | |
| JEKNOC11 | P21 | 2 | 12.456 | 8.0362 | 13.533 | 90 | 112.86 | 90 | 1.098 | |
| JEKNOC12 | P21 | 2 | 12.109 | 7.9598 | 13.3618 | 90 | 111.951 | 90 | 1.147 | |
| JEKNOC13 | P21 | 2 | 12.368 | 8.021 | 13.536 | 90 | 112.24 | 90 | 1.102 | |
| JEKNOC14 | P21 | 2 | 12.368 | 8.021 | 13.536 | 90 | 112.24 | 90 | 1.102 | |
| JEKNOC15 | P21 | 2 | 12.368 | 8.021 | 13.536 | 90 | 112.24 | 90 | 1.102 | |
| JEKNOC16 | P21 | 2 | 12.368 | 8.021 | 13.536 | 90 | 112.24 | 90 | 1.102 | |
| JEKNOC17 | P21 | 2 | 12.368 | 8.021 | 13.536 | 90 | 112.24 | 90 | 1.102 |
Table . Experimental information for CSD entries for Ibuprofen.
| REFCODE | space group | R factor | T / K | Year | Comments |
|---|---|---|---|---|---|
| IBPRAC | P21/c | 3.9 | 295 | 1974 | Reference not online |
| IBPRAC01 | P21/c | 5.3 | 100 | 1996 | Neutron data, recrystallized from acetonitrile1 |
| IBPRAC02 | P21/c | 5.3 | 100 | 1997 | See IBPRAC012 |
| IBPRAC03 | P21/c | 0 | 295 | 2009 | Synchrotron data, mixtures with acetaminophen prepared from commercial tablets3 |
| IBPRAC04 | P21/c | 5.8 | 258 | 2010 | Powder diffraction, high temperature annealing4 |
| IBPRAC05 | P21/c | 8.33 | 296 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC06 | P21/c | 5.36 | 296 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC07 | P21/c | 8.17 | 296 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC08 | P21/c | 10.66 | 296 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC09 | P21/c | 8.3 | 296 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC10 | P21/c | 9.95 | 296 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC11 | P21/c | 19.04 | 296 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC12 | P21/c | 11.93 | 296 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC13 | P21/c | 11.85 | 296 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC14 | P21/c | 10.03 | 296 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC15 | P21/c | 11.18 | 296 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC16 | P21/c | 4.24 | 100 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC17 | P21/c | 4.51 | 150 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC18 | P21/c | 4.64 | 200 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC19 | P21/c | 4.84 | 250 | 2015 | Under pressure, with chiral coformers or in chiral solvents5 |
| IBPRAC20 | P21/c | 25.41 | 293 | 2018 | Electron diffraction, Kroger-branded ibuprofen tablets, crushed with pestle and mortar6 |
| IBPRAC21 | P21/c | 1.44 | 25 | 2020 | Synchrotron data, slow evaporation of a saturated methanol solution7 |
| IBPRAC22 | P21/c | 25.41 | 293 | 2020 | See IBPRAC20 |
| JEKNOC | P21 | 6.3 | 295 | 1990 | Reference not online |
| JEKNOC10 | P21 | 5.6 | 295 | 1993 | From methanol (supplied by Boots chemicals)8 |
| JEKNOC11 | P21 | 3.85 | 323 | 2003 | Slow evaporation from n-heptanol solution9 |
| JEKNOC12 | P21 | 3.8 | 99 | 2011 | Slow evaporation from methanol solution10 |
| JEKNOC13 | P21 | 17.94 | 95 | 2023 | Electron diffraction, not specified11 |
| JEKNOC14 | P21 | 19.11 | 95 | 2023 | Electron diffraction, not specified11 |
| JEKNOC15 | P21 | 18.82 | 95 | 2023 | Electron diffraction, not specified11 |
| JEKNOC16 | P21 | 19.01 | 95 | 2023 | Electron diffraction, not specified11 |
| JEKNOC17 | P21 | 19.02 | 95 | 2023 | Electron diffraction, not specified11 |
Make this table include whether polymorphs are solution-grown, sublimation grown, templated or otherwise. Add references.
The structure matching is poor. Structure matches with CrystalPredictor are outside RMSD30=0.3 Å (it was CrystalPredictor 1.9, so the molecule is made up of rigid fragments and is not a good match). Matches to racemic form 2 are also not good, because the form 2 structure is poor. Old manual matching is retained, rather than stating that nothing much matches and the searches were unsuccessful.
1. N. Shankland, A. J. Florence, P. J. Cox, D. B. Sheen, S. W. Love, N. S. Stewart and C. C. Wilson, Chemical Communications, 1996, 855-856.
2. N. Shankland, C. C. Wilson, A. J. Florence and P. J. Cox, Acta Crystallographica Section C - Crystal Structure Communications, 1997, 53, 951-954.
3. K. H. Stone, S. H. Lapidus and P. W. Stephens, Journal of Applied Crystallography, 2009, 42, 385-391.
4. P. Derollez, E. Dudognon, F. Affouard, F. Danede, N. T. Correia and M. Descamps, Acta Crystallographica Section B, 2010, 66, 76-80.
5. K. Ostrowska, M. Kropidlowska and A. Katrusiak, Crystal Growth & Design, 2015, 15, 1512-1517.
6. 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.
7. F. Kleemiss, A. Justies, D. Duvinage, P. Watermann, E. Ehrke, K. Sugimoto, M. Fugel, L. A. Malaspina, A. Dittmer, T. Kleemiss, P. Puylaert, N. R. King, A. Staubitz, T. M. Tzschentke, R. Dringen, S. Grabowsky and J. Beckmann, Journal of Medicinal Chemistry, 2020, 63, 12614-12622.
8. A. A. Freer, J. M. Bunyan, N. Shankland and D. B. Sheen, Acta Crystallographica Section C, 1993, 49, 1378-1380.
9. L. K. Hansen, G. L. Perlovich and A. Bauer-Brandl, Acta Crystallographica Section E, 2003, 59, o1357-o1358.
10. M. D. King, W. D. Buchanan and T. M. Korter, Journal of Pharmaceutical Sciences, 2011, 100, 1116-1129.
11. M. Khouchen, P. B. Klar, H. Chintakindi, A. Suresh and L. Palatinus, Acta Crystallographica Section A, 2023, 79, 427-439.