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Volume 68 
Part 1 
Page o92  
January 2012  

Received 1 December 2011
Accepted 6 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.107
Data-to-parameter ratio = 16.0
Details
Open access

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

aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan,bDepartment of Chemistry, Government College University, Faisalabad 3800, Pakistan, and cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
Correspondence e-mail: drhamidlatif@yahoo.com

In the title molecule, C23H17NO5S, the heterocyclic thiazine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.383 (3) and 0.473 (3) Å, respectively, on opposite sides of the mean plane formed by the ring C atoms. The phenyl rings attached to carbonyl groups lie almost parallel to each other at a dihedral angle 7.43 (9)°, the distance between the centroids of the rings being 3.780 (1) Å. The C(thiazine)-C=O and O=C-CH2 groups make dihedral angles of 37.56 (16) and 1.93 (18)°, respectively, with the phenyl groups to which they are attached. The crystal structure features O-H...O and C-H...O hydrogen bonds and further consolidated by C-H...[pi] interactions; an intramolecular O-H...O hydrogen bond is also present.

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.]); Siddiqui et al. (2007[Siddiqui, W. A., Ahmad, S., Khan, I. U., Siddiqui, H. L. & Weaver, G. W. (2007). Synth. Commun. 37, 767-773.]). 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
  • C23H17NO5S

  • Mr = 419.44

  • Triclinic, [P \overline 1]

  • a = 7.5458 (2) Å

  • b = 10.9169 (4) Å

  • c = 12.0924 (4) Å

  • [alpha] = 101.920 (2)°

  • [beta] = 101.423 (2)°

  • [gamma] = 90.484 (2)°

  • V = 954.08 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 173 K

  • 0.24 × 0.14 × 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 = 0.952, Tmax = 0.976

  • 8312 measured reflections

  • 4362 independent reflections

  • 3706 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.107

  • S = 1.07

  • 4362 reflections

  • 272 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10-C15 ring.

D-H...A D-H H...A D...A D-H...A
O3-H3O...O4i 0.84 2.43 3.026 (2) 129
C5-H5...O5ii 0.95 2.52 3.311 (2) 140
C22-H22...O3iii 0.95 2.57 3.346 (2) 139
O3-H3O...O4 0.84 1.80 2.537 (2) 146
C16-H16B...Cg1iv 0.99 2.78 3.455 (2) 126
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y, -z+1; (iii) x, y-1, z; (iv) x+1, y, 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: 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: WN2461 ).


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.
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., Khan, I. U., Siddiqui, H. L. & Weaver, G. W. (2007). Synth. Commun. 37, 767-773.  [ISI] [CrossRef] [ChemPort]
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, o92  [ doi:10.1107/S1600536811052615 ]

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