N-(2-Chlorophenyl)-4-hydroxy-2H-1,2- benzothiazine-3-carboxamide 1,1-dioxide Waseeq Ahmad Siddiqui, a * Hamid Latif Siddiqui, b Muhammad Azam, c Masood Parvez d and Umar Farooq Rizvi b a Department of Chemistry, University of Sargodha, Sargodha 40100, Pakistan, b Institute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, c Institute of Biochemistry, University of Balochistan, Quetta, Pakistan, and d Department of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4 Correspondence e-mail: waseeqsiddiqui@gmail.com Received 19 August 2009; accepted 25 August 2009 Key indicators: single-crystal X-ray study; T = 200 K; mean (C–C) = 0.003 A ˚ ; R factor = 0.041; wR factor = 0.101; data-to-parameter ratio = 15.5. In the title compound, C 15 H 11 ClN 2 O 4 S, there are two independent molecules in the asymmetric unit, in which the heterocyclic thiazine rings in both molecules adopt half-chair conformations. The conformations about the C—C and C—N bonds in the central C—C—N—C chain in both molecules are all EZ. There are strong intramolecular O—HO and N— HN hydrogen bonds resulting in graph-set patterns S(6) and S(5) for the oxo and amino rings, in addition to intramolecular N—HCl interactions. In the crystal struc- ture, molecules are linked by intermolecular O—HO and N—HO hydrogen bonds into chains along [100]. Related literature For details of the synthesis, see: Siddiqui et al. (2008). For background to benzothiazine carboxamide derivatives as analgesic and anti-inflammatory agents, see: Myung et al. (2002); Shin et al. (2000); Banerjee & Sarkar (2002). For related structures, see: Siddiqui et al. (2006, 2007, 2008). Allen et al. (1987). For hydrogen-bond patterns and graph sets, see: Bernstein et al. (1994). Experimental Crystal data C 15 H 11 ClN 2 O 4 S M r = 350.77 Monoclinic, P2 1 =c a = 10.077 (2) A ˚ b = 13.818 (3) A ˚ c = 21.426 (4) A ˚  = 97.070 (13)  V = 2960.8 (10) A ˚ 3 Z =8 Mo K radiation  = 0.42 mm 1 T = 200 K 0.16  0.14  0.12 mm Data collection Nonius KappaCCD diffractometer Absorption correction: multi-scan (SORTAV; Blessing, 1997) T min = 0.936, T max = 0.951 12965 measured reflections 6732 independent reflections 5711 reflections with I >2(I) R int = 0.031 Refinement R[F 2 >2(F 2 )] = 0.041 wR(F 2 ) = 0.101 S = 1.05 6732 reflections 433 parameters H atoms treated by a mixture of independent and constrained refinement Á max = 0.33 e A ˚ 3 Á min = 0.39 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ ,  ). D—HA D—H HA DA D—HA O3—H3OO4 0.83 (3) 1.89 (3) 2.612 (2) 144 (3) O3—H3OO4 i 0.83 (3) 2.33 (3) 2.854 (2) 122 (2) O7—H7OO8 0.89 (3) 1.81 (3) 2.607 (2) 147 (2) O7—H7OO8 ii 0.89 (3) 2.46 (3) 2.964 (2) 116 (2) N1—H1NO8 ii 0.87 (2) 2.06 (2) 2.911 (2) 164 (2) N2—H2NN1 0.82 (2) 2.24 (2) 2.700 (2) 116 (2) N2—H2NCl1 0.82 (2) 2.47 (2) 2.930 (2) 116 (2) N3—H3NO4 i 0.89 (2) 2.07 (2) 2.912 (2) 157 (2) N4—H4NN3 0.88 (2) 2.23 (2) 2.692 (2) 113 (2) N4—H4NCl2 0.88 (2) 2.41 (2) 2.934 (2) 119 (2) Symmetry codes: (i) x þ 2; y þ 1; z þ 1; (ii) x þ 1; y þ 1; z þ 1. Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALE- PACK (Otwinowski & Minor, 1997); 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: LH2886). References Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, S1–19. Banerjee, R. & Sarkar, M. (2002). J. Lumin. 99, 255–263. Bernstein, J., Etter, M. C. & Leiserowitz, L. (1994). Structute Correlation, Vol. 2, edited by H.-B. Bu ¨rgi & J. D. Dunitz, pp. 431–507. New York: VCH Publishers. Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Myung, S. P., Eun, S. C., Myung, S. L. & Soon-kyoung, K.(2002). Bull. Korean Chem. Soc. 23, 1836–1838. organic compounds Acta Cryst. (2009). E65, o2279–o2280 doi:10.1107/S1600536809033972 Siddiqui et al. o2279 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368