Abstract
The crystal structure of the N,N-dimethylacetamide–biclotymol 1:1 solvate has been determined at room temperature by X-ray single-crystal diffraction. The molecular geometry of the biclotymol molecule is compared to the geometries observed in the N,N-dimethylformamide and dimethylsulfoxide solvates, and in the unsolvated form Phase-I. Rotational energy profile of the isolated molecule was obtained by semi-empirical AM1 calculations with respect to two selected torsional angles, which were rotated from 0° to 360° by steps of 10°. Not only, we find the two conformations experimentally observed, but also the conformation proposed by simple force fields calculations 30 years ago. Moreover, we propose three additional possible conformations that may offer potential candidates for the structure biclotymol Phase-II, which remains to be solved.
Similar content being viewed by others
References
Harris KDM, Tremayne M, Kariuki BM (2001) Angew Chem Ind Ed 40:1626
David WIF, Shankland K (2008) Acta crystallogr A64:52
Middleton DA, Peng X, Saunders D, Shankland K, David WIF, Markvardsen AJ (2002) Chem Commun 1976
Rantsordas S, Perrin M, Thozet A (1978) Acta Crystallogr B34:1198
Rantsordas S, Perrin M, Thozet A, Lecocq S (1981) Acta crystallogr B37:1253
Rantsordas S, Perrin M (1982) Acta crystallogr B38:1871
Chetkina LA, Nelsky VK (2005) Crystallogr Rep 50(4):622
Céolin R, Tamarit JL, Barrio M, Lopez DO, Nicolaï B, Veglio N, Perrin M-A, Espeau P (2008) J Pharm Sci 97(9):3927
Brittain HG (1999) Polymorphism in pharmaceutical solids. Marcel Dekker, New York
Brittain HG (2009) J Pharm Sci 98(5):1617
Mahé N, Nicolaï B, Céolin R (2008) X ray structure analysis 24:x143
Mahé N, Nicolaï B, Céolin R (2008) X ray structure analysis 24:x193
Rantsordas S, Royer J, Tinland B (1986) J Mole Struct (THEOCHEM) 136:147
Enraf-Nonius, CAD4 Express Software, Enraf-Nonius, Delft, The Nederlands (1994)
Harms K, Wocadlo S (1995) XCAD-CAD4 Data reduction. University of Marburg, Marburg
Altomare A, Burla MC, Camalli M, Cascarano GL, Giacovazzo C, Guagliardi A, Moliterni AGG, Polidori G, Spagna R (1999) J Appl Cryst 32:115
Sheldrick GM (2008) Acta Crystallogr A64:112
Farrugia LJ (1999) J Appl Cryst 32:837
Spek AL (2003) J Appl Cryst 36:7
Spek AL (2008) PLATON, A multipurpose crystallographic tool. Utrecht University, Utrecht
Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP (1985) J Am Chem Soc 107:3902
Stewart JJP (1990) J Comput Aided Mol Des 4:1
Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su SJ, Windus TL, Dupuis M, Montgomery JA (1993) J Comput Chem 14:1347
Gordon MS, Schmidt MW (2005) Theory and applications of computational chemistry, the first forty years. In: Dykstra CE, Frenking G, Kim KS, Scuseria GE (eds) Elsevier, Amsterdam
Schaftenaar G, Noordik JH (2000) J Comput Aided Mol Des 14:123
Grabowski J (2006) Challenges and advances in computational chemistry and physics. In: Grabowski S (ed) Hydrogen bonding—new insights, vol 3. Springer, Dordrecht
Aknowledgements
The authors aknowledge Dr. Philippe Bénas (Université Paris Descartes) for kind assistance in single-crystal X-ray diffraction collection, and Mrs E. Moreau (Bouchara-Recordati, France) for the gift of biclotymol samples. The authors are also grateful to Pr R. Céolin for helpful discussions.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Nicolaï, B., Mahé, N. Crystal structure of the biclotymol–N,N-dimethylacetamide solvate 1:1: experimental and theoretical conformational analysis of biclotymol molecule. Struct Chem 21, 503–510 (2010). https://doi.org/10.1007/s11224-009-9578-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11224-009-9578-x