2-(3-Benzoyl-4-hy­droxy-1,1-dioxo-2H-1λ6,2-benzothia­zin-2-yl)-1-phenyl­ethanone

Sattar, N.; Siddiqui, H.L.; Bukhari, S.I.H.; Ahmad, M.; Parvez, M.

doi:10.1107/S1600536811052615

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 (C-C) = 0.003 Å
R = 0.044
wR = 0.107
Data-to-parameter ratio = 16.0
Details

2-(3-Benzoyl-4-hydroxy-1,1-dioxo-2H-1⁶,2-benzothiazin-2-yl)-1-phenylethanone

Nazia Sattar,^a Hamid Latif Siddiqui,^a ^* Syed Iftikhar Hussain Bukhari,^b Matloob Ahmad ^a and Masood Parvez ^c

^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-HO and C-HO hydrogen bonds and further consolidated by C-H [pi] interactions; an intramolecular O-HO hydrogen bond is also present.

Related literature

For the biological activity of benzothiazine derivatives, see: Ahmad et al. (2010); Siddiqui et al. (2007). For related structures, see: Siddiqui et al. (2008).

Experimental

Crystal data

C₂₃H₁₇NO₅S
M_r = 419.44
Triclinic, $[P \overline 1]$
a = 7.5458 (2) Å
b = 10.9169 (4) Å
c = 12.0924 (4) Å
= 101.920 (2)°
= 101.423 (2)°
= 90.484 (2)°
V = 954.08 (5) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.952, T_max = 0.976
8312 measured reflections
4362 independent reflections
3706 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.107
S = 1.07
4362 reflections
272 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10-C15 ring.

D-HA	D-H	HA	DA	D-HA
O3-H3OO4ⁱ	0.84	2.43	3.026 (2)	129
C5-H5O5ⁱⁱ	0.95	2.52	3.311 (2)	140
C22-H22O3ⁱⁱⁱ	0.95	2.57	3.346 (2)	139
O3-H3OO4	0.84	1.80	2.537 (2)	146
C16-H16BCg1^iv	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); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (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: 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.
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.
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.
Siddiqui, W. A., Ahmad, S., Khan, I. U., Siddiqui, H. L. & Weaver, G. W. (2007). Synth. Commun. 37, 767-773.
Siddiqui, W. A., Ahmad, S., Tariq, M. I., Siddiqui, H. L. & Parvez, M. (2008). Acta Cryst. C64, o4-o6.