Copyright (c) 2017 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Study of Polymorphic Behaviour of 2,2'-Dichloro benzil Using Dynamic Thermal and X-Ray Diffraction Technique
Corresponding Author(s) : G. Nithya
Asian Journal of Chemistry,
Vol. 29 No. 10 (2017): Vol 29 Issue 10
Abstract
2,2’-Dichloro benzil (1) was synthesized and its two polymorphic forms were obtained by recrystallization from the solvents acetone/chloroform and ethanol. The polymorphism present in the compound was confirmed by combined results of differential scanning calorimetry and single crystal X-ray crystallography. Each molecule crystallizes with one molecule in the asymmetric unit and the molecular conformations are quite different for both. The polymorph 1a crystallizes as monoclinic c2/c space group in the solvent ethanol and the polymorph 1b crystallizes as monoclinic P21/c space group in the solvent THF. X-ray crystal structures of conformational polymorphs were analyzed to understand the interplay of molecular conformation and intermolecular lattice energy in the crystallization and stability of polymorphs.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- J. Bernstein, Polymorphism in Molecular Crystals, Clarendon Press, Oxford (2002).
- R. Hilfiker, Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim (2006).
- J.D. Dunitz and J. Bernstein, Acc. Chem. Res., 28, 193 (1995); https://doi.org/10.1021/ar00052a005.
- A. Bond, Curr. Opin. Solid State Mater. Sci., 13, 91 (2009); https://doi.org/10.1016/j.cossms.2009.06.004.
- F. Grepioni, New J. Chem., 32, 1657 (2008); https://doi.org/10.1039/b814474p.
- Y. Fan, W. Song, D. Yu, K. Ye, J. Zhang and Y. Wang, CrystEngComm, 11, 1716 (2009); https://doi.org/10.1039/b902129a.
- A. Beheshti, W. Clegg, N. Ebrahimi Filoori and L. Russo, Acta Crystallogr. C, 67, 149 (2011); https://doi.org/10.1107/S0108270111013035.
- A. Collas, M. Zeller and F. Blockhuys, Acta Crystallogr. C, 67, 171 (2011); https://doi.org/10.1107/S0108270111010109.
- T. Steiner, Angew. Chem. Int. Ed., 41, 48 (2002); https://doi.org/10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U.
- (a) G.A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Structures; Springer-Verlag; Berlin (1991); (b) G.A. Jeffrey, An Introduction to Hydrogen Bonding; Oxford University Press, New York (1997).
- G.R. Desiraju, Acc. Chem. Res., 35, 565 (2002); https://doi.org/10.1021/ar010054t.
- G.R. Desiraju and T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University, UK (1999).
- C.P. Brock and R.P. Minton, J. Am. Chem. Soc., 111, 4586 (1989); https://doi.org/10.1021/ja00195a010.
- R. Hiltiker, Polymorphism in the Pharmaceutical Industry; Wiley-VCH:Weinheim, Germany (2006).
- A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi, J. Appl. Cryst., 26, 343 (1993); https://doi.org/10.1107/S0021889892010331.
- G.M. Sheldrick, Acta Cryst., A64, 112 (2008); https://doi.org/10.1107/S0108767307043930.
- H.G. Brittain, J. Pharm. Sci., 96, 705 (2007); https://doi.org/10.1002/jps.20772
References
J. Bernstein, Polymorphism in Molecular Crystals, Clarendon Press, Oxford (2002).
R. Hilfiker, Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim (2006).
J.D. Dunitz and J. Bernstein, Acc. Chem. Res., 28, 193 (1995); https://doi.org/10.1021/ar00052a005.
A. Bond, Curr. Opin. Solid State Mater. Sci., 13, 91 (2009); https://doi.org/10.1016/j.cossms.2009.06.004.
F. Grepioni, New J. Chem., 32, 1657 (2008); https://doi.org/10.1039/b814474p.
Y. Fan, W. Song, D. Yu, K. Ye, J. Zhang and Y. Wang, CrystEngComm, 11, 1716 (2009); https://doi.org/10.1039/b902129a.
A. Beheshti, W. Clegg, N. Ebrahimi Filoori and L. Russo, Acta Crystallogr. C, 67, 149 (2011); https://doi.org/10.1107/S0108270111013035.
A. Collas, M. Zeller and F. Blockhuys, Acta Crystallogr. C, 67, 171 (2011); https://doi.org/10.1107/S0108270111010109.
T. Steiner, Angew. Chem. Int. Ed., 41, 48 (2002); https://doi.org/10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U.
(a) G.A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Structures; Springer-Verlag; Berlin (1991); (b) G.A. Jeffrey, An Introduction to Hydrogen Bonding; Oxford University Press, New York (1997).
G.R. Desiraju, Acc. Chem. Res., 35, 565 (2002); https://doi.org/10.1021/ar010054t.
G.R. Desiraju and T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University, UK (1999).
C.P. Brock and R.P. Minton, J. Am. Chem. Soc., 111, 4586 (1989); https://doi.org/10.1021/ja00195a010.
R. Hiltiker, Polymorphism in the Pharmaceutical Industry; Wiley-VCH:Weinheim, Germany (2006).
A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi, J. Appl. Cryst., 26, 343 (1993); https://doi.org/10.1107/S0021889892010331.
G.M. Sheldrick, Acta Cryst., A64, 112 (2008); https://doi.org/10.1107/S0108767307043930.
H.G. Brittain, J. Pharm. Sci., 96, 705 (2007); https://doi.org/10.1002/jps.20772