Received 12 July 2012
aDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan,bInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, and cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
Correspondence e-mail: email@example.com
In the title molecule, C20H19FN4O3S, the heterocyclic thiazine ring adopts a half-chair conformation with the S atom displaced by 0.668 (4) Å from the mean plane formed by the remaining ring atoms. The mean planes of the benzene and pyrazole rings are inclined with respect to each other at a dihedral angle of 17.4 (3)°. The acetamide chain (O/N/C/C/C) linking the pyrazole and 2-fluorobenzyl rings is essentially planar (r.m.s. deviation = 0.030 Å) and forms dihedral angles with the mean planes of these rings of 78.8 (2) and 78.89 (14)°, respectively. The crystal structure is stabilized by N-HO and C-HO hydrogen-bonding interactions, resulting in a six-membered ring with an R21(6) motif, while C-HO and C-HF hydrogen-bonding interactions result in chains of molecules lying along the c axis in a zigzag fashion.
For biological activities of benzothiazine derivatives, see: Turck et al. (1996); Silverstein et al. (2000); Lombardino et al. (1973); Zinnes et al. (1973); Ahmad, Siddiqui, Ahmad et al. (2010); Ahmad, Siddiqui, Zia-ur-Rehman & Parvez (2010). For related crystal structures, see: Siddiqui et al. (2008, 2009). For graph-set notations, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2076 ).
The authors are grateful to the Higher Education Commission, Pakistan, and Institute of Chemistry, University of the Punjab, Lahore, Pakistan, for financial support.
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