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Synthesis and Crystal Structure of [2-Chloro-4-(methylsulfonyl)phenyl]methanol
Corresponding Author(s) : Chuan Zhang
Asian Journal of Chemistry,
Vol. 26 No. 16 (2014): Vol 26 Issue 16
Abstract
The crystal structure of the [2-chloro-4-(methylsulfonyl)phenyl]methanol has been determined by single crystal X-ray diffraction method. The crystal belongs to monoclinic, space group P2(1)/c, with a = 8.208(4), b = 4.870 (2), c = 23.349 (10) Å, a = 90, b = 97.160 (6), g = 90°, V = 926.0 (7)Å3, Z = 4, Dx = 1.583 Mg/m3, l(MoKa) = 0.71073, F(000) = 456, μ(MoKa) = 0.607 mm-1, R = 0.0506 and wR = 0.1231 for 0.1263 reflections with I > 2s (I). The S atom has a distorted tetrahedral geometry with bond angles ranging from 103.03 (12)° to 118.13 (13)°. The crystal structure is stabilized by intermolecular hydrogen bonds and p-p stacking interactions.
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References
P.G. De Benedetti, U. Folli, D. Iarossi and C. Frassineti, J. Chem. Soc. Perkin Trans. II, 1527 (1985); doi:10.1039/p29850001527.
D. Dubé, C. Brideau, D. Deschênes, R. Fortin, R.W. Friesen, R. Gordon, Y. Girard, D. Riendeau, C. Savoie and C.-C. Chan, Bioorg. Med. Chem. Lett., 9, 1715 (1999); doi:10.1016/S0960-894X(99)00264-4.
F. Wuest, X. Tang, T. Kniess, J. Pietzsch and M. Suresh, Bioorg. Med. Chem. Lett., 17, 1146 (2009); doi:10.1016/j.bmc.2008.12.032.
S. Ovais, K. Javed, S. Yaseen, R. Bashir, P. Rathore, R. Yaseen, A.D. Hameed and M. Samim, Eur. J. Med. Chem., 67, 352 (2013); doi:10.1016/j.ejmech.2013.06.050.
A.G. Romero, W.H. Darlington, M.F. Piercey and R.A. Lahti, Bioorg. Med. Chem. Lett., 2, 1703 (1992); doi:10.1016/S0960-894X(00)80460-6.
G. Gonzalez-Martin, C. Lyndon and C. Sunkel, Eur. J. Pharm. Biopharm., 46, 293 (1998); doi:10.1016/S0939-6411(98)00045-9.
T. Inoue, M. Morita, T. Tojo, A. Nagashima, A. Moritomo, K. Imai and H. Miyake, Bioorg. Med. Chem. Lett., 21, 2478 (2013); doi:10.1016/j.bmc.2013.02.048.
T. Iino, D. Tsukahara, K. Kamata, K. Sasaki, S. Ohyama, H. Hosaka, T. Hasegawa, M. Chiba, Y. Nagata, J.- Eiki and T. Nishimura, Bioorg. Med. Chem. Lett., 17, 2733 (2009); doi:10.1016/j.bmc.2009.02.038.
G.M. Sheldrick, Programs SMART and SHELXTL, Bruker AXS, Inc., Madison, WI, USA (2003).
G.M. Sheldrick, SHELXS-97, Program for the Solution of Crystal Structures and SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany (1997).
U. Sankar, V. Sabari, S. Mahalakshmi, K. K. Balasubramanian and S. Aravindhan, Acta Crystallogr., E69, o1387 (2013); doi:10.1107/S1600536813021429.
G. Chakkaravarthi, V. Dhayalan, A.K. Mohanakrishnan and V. Manivannan, Acta Crystallogr., E64, o542 (2008); doi:10.1107/S1600536808003024.