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Volume 68 
Part 1 
Page o91  
January 2012  

Received 1 December 2011
Accepted 7 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.006 Å
R = 0.079
wR = 0.164
Data-to-parameter ratio = 16.3
Details
Open access

3-[(3-Benzoyl-4-hydroxy-1,1-dioxo-2H-1[lambda]6,2-benzothiazin-2-yl)methyl]benzonitrile

aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, and bDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
Correspondence e-mail: drhamidlatif@yahoo.com

There are two independent molecules in the asymmetric unit of the title compound, C23H17N2O4S, with significant differences in their conformations, e.g. the benzene rings of the benzothiazine and benzonitrile units are inclined at 28.19 (10) and 17.89 (7)° in the two molecules, with the centroids of the rings separated by 3.975 (2) and 3.637 (2) Å, respectively. Moreover, the N-C-C-C torsion angles involving the benzoyl group are 14.3 (5) and 8.2 (5)° in the two molecules, showing different degrees of rotation of this group. In both molecules, the heterocyclic thiazine rings adopt half-chair conformations, with the S and N atoms displaced by 0.427 (6) and 0.365 (6) Å, respectively, in one molecule and by 0.356 (6) and 0.432 (6) Å, respectively, in the other, on opposite sides of the mean planes formed by the remaining ring atoms. The crystal structure is stabilized by intermolecular C-H...O hydrogen bonds and further consolidated by intramolecular O-H...O hydrogen bonds.

Related literature

For the biological activity of benzothiazine derivatives, see: Ahmad et al. (2010[Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M. & Parvez, M. (2010). Eur. J. Med. Chem. 45, 698-704.]). For related structures, see: Siddiqui et al. (2008[Siddiqui, W. A., Ahmad, S., Tariq, M. I., Siddiqui, H. L. & Parvez, M. (2008). Acta Cryst. C64, o4-o6.]).

[Scheme 1]

Experimental

Crystal data
  • C23H16N2O4S

  • Mr = 416.44

  • Orthorhombic, P b c a

  • a = 12.2900 (2) Å

  • b = 24.7970 (6) Å

  • c = 25.6080 (6) Å

  • V = 7804.2 (3) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 173 K

  • 0.20 × 0.12 × 0.12 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1997[Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.]) Tmin = 0.961, Tmax = 0.976

  • 16724 measured reflections

  • 8869 independent reflections

  • 6212 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.079

  • wR(F2) = 0.164

  • S = 1.13

  • 8869 reflections

  • 543 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.53 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16A...O3i 0.99 2.57 3.382 (4) 139
C16-H16B...O1i 0.99 2.60 3.456 (4) 145
C28-H28...O2ii 0.95 2.45 3.188 (4) 135
O3-H3O...O4 0.84 1.76 2.503 (4) 146
O7-H7O...O8 0.84 1.73 2.484 (4) 148
Symmetry codes: (i) [x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z].

Data collection: COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2435 ).


Acknowledgements

HLS is grateful to the Institute of Chemistry, University of the Punjab, Lahore, Pakistan, for financial support.

References

Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M. & Parvez, M. (2010). Eur. J. Med. Chem. 45, 698-704.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.  [CrossRef] [ChemPort] [ISI] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siddiqui, W. A., Ahmad, S., Tariq, M. I., Siddiqui, H. L. & Parvez, M. (2008). Acta Cryst. C64, o4-o6.  [CrossRef] [details]


Acta Cryst (2012). E68, o91  [ doi:10.1107/S1600536811052706 ]

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