The Third Ambient Aspirin Polymorph

Shtukenberg, Alexander G.; Hu, Chunhua T.; Zhu, Qiang; Schmidt, Martin U.; Xu, Wenqian; Tan, Melissa; Kahr, Bart

doi:10.1021/acs.cgd.7b00673

The Third Ambient Aspirin Polymorph

Journal Article · Wed May 17 00:00:00 EDT 2017 · Crystal Growth and Design

DOI:https://doi.org/10.1021/acs.cgd.7b00673· OSTI ID:1373897

^[1]; Hu, Chunhua T. ^[1]; Zhu, Qiang ^[2]; Schmidt, Martin U. ^[3]; Xu, Wenqian ^[4]; Tan, Melissa ^[1]; Kahr, Bart ^[5]

New York Univ., New York City, NY (United States)
Univ. of Nevada, Las Vegas, NV (United States)
Goethe Univ., Frankfurt am Main (Germany)
Argonne National Lab. (ANL), Argonne, IL (United States)
New York Univ., New York City, NY (United States); Waseda Univ., Tokyo (Japan)

Polymorphism in aspirin (acetylsalicylic acid), one of the most widely consumed medications, was equivocal until the structure of a second polymorph II, similar in structure to the original form I, was reported in 2005. Here, the third ambient polymorph of aspirin is described. Lastly, it was crystallized from the melt and its structure was determined using a combination of X-ray powder diffraction analysis and crystal structure prediction algorithms.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE National Nuclear Security Administration (NNSA); National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22), Scientific User Facilities Division

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1373897

Journal Information:: Crystal Growth and Design, Journal Name: Crystal Growth and Design Journal Issue: 6 Vol. 17; ISSN 1528-7483

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (27)

On the Polymorphism of Aspirin Bond, Andrew D.; Boese, Roland; Desiraju, Gautam R. Angewandte Chemie International Edition, Vol. 46, Issue 4 https://doi.org/10.1002/anie.200602378	journal	January 2007
On the Polymorphism of Aspirin: Crystalline Aspirin as Intergrowths of Two “Polymorphic” Domains Bond, Andrew D.; Boese, Roland; Desiraju, Gautam R. Angewandte Chemie International Edition, Vol. 46, Issue 4 https://doi.org/10.1002/anie.200603373	journal	January 2007
Growth Actuated Bending and Twisting of Single Crystals Shtukenberg, Alexander G.; Punin, Yurii O.; Gujral, Ankit Angewandte Chemie International Edition, Vol. 53, Issue 3 https://doi.org/10.1002/anie.201301223	journal	January 2014
The Structure of Glycine Dihydrate: Implications for the Crystallization of Glycine from Solution and Its Structure in Outer Space Xu, Wenqian; Zhu, Qiang; Hu, Chunhua Tony Angewandte Chemie International Edition, Vol. 56, Issue 8 https://doi.org/10.1002/anie.201610977	journal	January 2017
Extension of the CHARMM general force field to sulfonyl-containing compounds and its utility in biomolecular simulations Yu, Wenbo; He, Xibing; Vanommeslaeghe, Kenno Journal of Computational Chemistry, Vol. 33, Issue 31 https://doi.org/10.1002/jcc.23067	journal	July 2012
CHARMM: A program for macromolecular energy, minimization, and dynamics calculations Brooks, Bernard R.; Bruccoleri, Robert E.; Olafson, Barry D. Journal of Computational Chemistry, Vol. 4, Issue 2 https://doi.org/10.1002/jcc.540040211	journal	July 1983
New developments in evolutionary structure prediction algorithm USPEX Lyakhov, Andriy O.; Oganov, Artem R.; Stokes, Harold T. Computer Physics Communications, Vol. 184, Issue 4 https://doi.org/10.1016/j.cpc.2012.12.009	journal	April 2013
High-pressure polymorphism of acetylsalicylic acid (aspirin): Raman spectroscopy Crowell, Ethan L.; Dreger, Zbigniew A.; Gupta, Yogendra M. Journal of Molecular Structure, Vol. 1082 https://doi.org/10.1016/j.molstruc.2014.10.079	journal	February 2015
Evaluation of Shear-Slip Transitions in Crystalline Aspirin by Density-Functional Theory LeBlanc, Luc M.; Otero-de-la-Roza, Alberto; Johnson, Erin R. Crystal Growth & Design, Vol. 16, Issue 12 https://doi.org/10.1021/acs.cgd.6b01038	journal	October 2016
Toward Crystal Structure Prediction for Conformationally Flexible Molecules: The Headaches Illustrated by Aspirin Ouvrard, Carole; Price, Sarah L. Crystal Growth & Design, Vol. 4, Issue 6 https://doi.org/10.1021/cg049922u	journal	November 2004
Spherulites Shtukenberg, Alexander G.; Punin, Yuri O.; Gunn, Erica Chemical Reviews, Vol. 112, Issue 3 https://doi.org/10.1021/cr200297f	journal	November 2011
Parametrization and Benchmark of DFTB3 for Organic Molecules Gaus, Michael; Goez, Albrecht; Elstner, Marcus Journal of Chemical Theory and Computation, Vol. 9, Issue 1 https://doi.org/10.1021/ct300849w	journal	November 2012
The Predictably Elusive Form II of Aspirin Vishweshwar, Peddy; McMahon, Jennifer A.; Oliveira, Mark Journal of the American Chemical Society, Vol. 127, Issue 48 https://doi.org/10.1021/ja056455b	journal	December 2005
Twisted Aspirin Crystals Cui, Xiaoyan; Rohl, Andrew L.; Shtukenberg, Alexander Journal of the American Chemical Society, Vol. 135, Issue 9 https://doi.org/10.1021/ja400833r	journal	February 2013
Circular Birefringence of Banded Spherulites Cui, Xiaoyan; Shtukenberg, Alexander G.; Freudenthal, John Journal of the American Chemical Society, Vol. 136, Issue 14 https://doi.org/10.1021/ja5013382	journal	February 2014
Resorcinol Crystallization from the Melt: A New Ambient Phase and New “Riddles” Zhu, Qiang; Shtukenberg, Alexander G.; Carter, Damien J. Journal of the American Chemical Society, Vol. 138, Issue 14 https://doi.org/10.1021/jacs.6b01120	journal	March 2016
DFTB+, a Sparse Matrix-Based Implementation of the DFTB Method ^† Aradi, B.; Hourahine, B.; Frauenheim, Th. The Journal of Physical Chemistry A, Vol. 111, Issue 26 https://doi.org/10.1021/jp070186p	journal	July 2007
Single crystals of aspirin form II: crystallisation and stability Bond, Andrew D.; Solanko, Katarzyna A.; Parsons, Simon CrystEngComm, Vol. 13, Issue 2 https://doi.org/10.1039/C0CE00588F	journal	January 2011
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
Van der Waals density functionals applied to solids Klimeš, Jiří; Bowler, David R.; Michaelides, Angelos Physical Review B, Vol. 83, Issue 19 https://doi.org/10.1103/PhysRevB.83.195131	journal	May 2011
Role of Dispersion Interactions in the Polymorphism and Entropic Stabilization of the Aspirin Crystal Reilly, Anthony M.; Tkatchenko, Alexandre Physical Review Letters, Vol. 113, Issue 5 https://doi.org/10.1103/PhysRevLett.113.055701	journal	July 2014
COMPACK : a program for identifying crystal structure similarity using distances Chisholm, James Alexander; Motherwell, Sam Journal of Applied Crystallography, Vol. 38, Issue 1 https://doi.org/10.1107/S0021889804027074	journal	January 2005
Unit-cell refinement from powder diffraction scans Pawley, G. S. Journal of Applied Crystallography, Vol. 14, Issue 6 https://doi.org/10.1107/S0021889881009618	journal	December 1981
Indexing of powder diffraction patterns for low-symmetry lattices by the successive dichotomy method Boultif, A.; Louër, D. Journal of Applied Crystallography, Vol. 24, Issue 6 https://doi.org/10.1107/S0021889891006441	journal	December 1991
Constrained evolutionary algorithm for structure prediction of molecular crystals: methodology and applications Zhu, Qiang; Oganov, Artem R.; Glass, Colin W. Acta Crystallographica Section B Structural Science, Vol. 68, Issue 3 https://doi.org/10.1107/S0108768112017466	journal	May 2012
Aspirin: Dissolution Rates of Two Polymorphic Forms Tawashi, R. Science, Vol. 160, Issue 3823 https://doi.org/10.1126/science.160.3823.76	journal	April 1968
Monte Carlo indexing with McMaille Le Bail, A. Powder Diffraction, Vol. 19, Issue 3 https://doi.org/10.1154/1.1763152	journal	September 2004

Cited By (10)

Confinement-induced polymorphism in acetylsalicylic acid–nanoporous glass composites Peksa, P.; Trzmiel, J.; Ptak, M. Journal of Materials Science, Vol. 54, Issue 1 https://doi.org/10.1007/s10853-018-2853-8	journal	August 2018
Structure prediction drives materials discovery Oganov, Artem R.; Pickard, Chris J.; Zhu, Qiang Nature Reviews Materials, Vol. 4, Issue 5 https://doi.org/10.1038/s41578-019-0101-8	journal	April 2019
Polymorphism of griseofulvin: concomitant crystallization from the melt and a single crystal structure of a metastable polymorph with anomalously large thermal expansion Su, Yuan; Xu, Jia; Shi, Qin Chemical Communications, Vol. 54, Issue 4 https://doi.org/10.1039/c7cc07744k	journal	January 2018
ROY revisited, again: the eighth solved structure Tan, Melissa; Shtukenberg, Alexander G.; Zhu, Shengcai Faraday Discussions, Vol. 211 https://doi.org/10.1039/c8fd00039e	journal	January 2018
Evolutionary niching in the GAtor genetic algorithm for molecular crystal structure prediction Curtis, Farren; Rose, Timothy; Marom, Noa Faraday Discussions, Vol. 211 https://doi.org/10.1039/c8fd00067k	journal	January 2018
Is zeroth order crystal structure prediction (CSP_0) coming to maturity? What should we aim for in an ideal crystal structure prediction code? Price, Sarah L. Faraday Discussions, Vol. 211 https://doi.org/10.1039/c8fd00121a	journal	January 2018
Probing stress induced phase transformation in aspirin polymorphs using Raman spectroscopy enabled nanoindentation Manimunda, Praveena; Syed Asif, S. A.; Mishra, Manish Kumar Chemical Communications, Vol. 55, Issue 62 https://doi.org/10.1039/c9cc04538d	journal	January 2019
Discovery of new polymorphs of the tuberculosis drug isoniazid Zhang, Keke; Fellah, Noalle; Shtukenberg, Alexander G. CrystEngComm https://doi.org/10.1039/d0ce00440e	journal	January 2020
Control and prediction of the organic solid state: a challenge to theory and experiment Price, Sarah L. Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 474, Issue 2217 https://doi.org/10.1098/rspa.2018.0351	journal	September 2018
Structure Prediction Drives Materials Discovery Oganov, Artem; Pickard, Christopher; Zhu, Qiang Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.39313	text	January 2019

Figures / Tables (5)

Similar Records

Disorderly Conduct of Benzamide IV: Crystallographic and Computational Analysis of High Entropy Polymorphs of Small Molecules

Journal Article · Wed Mar 11 00:00:00 EDT 2020 · Crystal Growth and Design · OSTI ID:1631968

Melt Crystallization for Paracetamol Polymorphism

Journal Article · Mon Jun 17 00:00:00 EDT 2019 · Crystal Growth and Design · OSTI ID:1564084

Powder diffraction and crystal structure prediction identify four new coumarin polymorphs

Journal Article · Mon May 15 00:00:00 EDT 2017 · Chemical Science · OSTI ID:1426142

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

CCDC 1541529: Experimental Crystal Structure Determination: ACSALA23 : 2-(acetyloxy)benzoic acid Shtukenberg, Alexander; Hu, Chunhua; Zhu, Qiang https://doi.org/10.5517/ccdc.csd.cc1nr2r7 The current record is supplemented by this dataset	dataset	March 2017
CCDC 1541530: Experimental Crystal Structure Determination: ACSALA24 : 2-(acetyloxy)benzoic acid Shtukenberg, Alexander; Hu, Chunhua; Zhu, Qiang https://doi.org/10.5517/ccdc.csd.cc1nr2s8 The current record is supplemented by this dataset	dataset	March 2017

The Third Ambient Aspirin Polymorph

Citation Formats

References (27)

Cited By (10)

Linked Research (2)

Figures / Tables (5)

Similar Records

Related Subjects