2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo­[4,3-c][1,2]benzothia­zin-2-yl)-N-(3-meth­oxy­benz­yl)acetamide

Ahmad, M.; Siddiqui, H.L.; Zia-ur-Rehman, M.; Aslam, S.; Parvez, M.

doi:10.1107/S1600536812040226

Volume 68
Part 11
Pages o3064-o3065
November 2012

Received 16 September 2012
Accepted 22 September 2012
Online 3 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.098
Data-to-parameter ratio = 14.6
Details

2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo[4,3-c][1,2]benzothiazin-2-yl)-N-(3-methoxybenzyl)acetamide

Matloob Ahmad,^a ^* Hamid Latif Siddiqui,^b Muhammad Zia-ur-Rehman,^c Sana Aslam ^b and Masood Parvez ^d

^aDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan,^bInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan,^cApplied Chemistry Research Center, PCSIR Laboratories Complex, Lahore 54600, Pakistan, and ^dDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
Correspondence e-mail: matloob_123@yahoo.com

The asymmetric unit of the title compound, C₂₁H₂₂N₄O₄S, contains two molecules (A and B), in which the thiazine rings adopt an S-envelope conformation with the S atoms displaced by 0.621 (2) and 0.697 (2) Å from the mean planes formed by the remaining ring atoms. The dihedral angles between the N-methylacetamide groups and the methoxybenzene rings are 8.67 (10) and 54.49 (6)° in the two molecules and the equivalent torsion angles in the N-methylacetamide chains connecting the ring systems also differ. In the crystal, N-HO hydrogen bonds connect the components into C(4) [100] chains of alternating A and B molecules. The packing is consolidated by weak C-HO interactions, which generate a three-dimensional network.

Related literature

For therapeutic applications of benzothiazines, see: Turck et al. (1996); Lombardino et al. (1973); Zinnes et al. (1973). For therapeutic applications of pyrrazoles, see: Silverstein et al. (2000). For the properties and crystal structures of related pyrazolobenzothiazine derivatives, see: Ahmad et al. (2010a,b, 2012; 2011a,b).

Experimental

Crystal data

C₂₁H₂₂N₄O₄S
M_r = 426.49
Monoclinic, P 2₁ /c
a = 8.6541 (1) Å
b = 25.8809 (3) Å
c = 18.3892 (2) Å
= 92.208 (1)°
V = 4115.68 (8) Å³
Z = 8
Cu K radiation
= 1.71 mm^-1
T = 173 K
0.14 × 0.12 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.796, T_max = 0.967
70993 measured reflections
7975 independent reflections
6621 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.098
S = 1.02
7975 reflections
547 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4NO7ⁱ	0.88	2.12	2.9511 (17)	158
N8-H8NO3ⁱⁱ	0.88	2.02	2.8928 (18)	171
C10-H10CO6ⁱⁱⁱ	0.98	2.45	3.349 (2)	152
C12-H12AO7ⁱ	0.99	2.56	3.2099 (19)	123
C14-H14AN6ⁱⁱ	0.99	2.58	3.556 (2)	168
C16-H16O7ⁱ	0.95	2.43	3.369 (2)	172
C25-H25O4^iv	0.95	2.47	3.365 (2)	156
C31-H31CO2^v	0.98	2.49	3.203 (2)	129
C33-H33AO3ⁱⁱ	0.99	2.46	3.320 (2)	145
C33-H33BO5^vi	0.99	2.45	3.352 (2)	151
C40-H40O2	0.95	2.59	3.367 (3)	139
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x-1, y, z+1; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: HB6961 ).

Acknowledgements

The authors are grateful to the Higher Education Commission, Pakistan, and the Institute of Chemistry, University of the Punjab, Lahore, Pakistan, for financial support.

References

Ahmad, M., Siddiqui, H. L., Ahmad, S., Parvez, M. & Tizzard, G. J. (2010a). J. Chem. Crystallogr. 40, 1188-1194.
Ahmad, M., Siddiqui, H. L., Gardiner, J. M., Parvez, M. & Aslam, S. (2012). Med. Chem. Res. doi:10.1007/s00044-012-0062-6.
Ahmad, M., Siddiqui, H. L., Khattak, M. I., Ahmad, S. & Parvez, M. (2011a). Acta Cryst. E67, o216-o217.
Ahmad, M., Siddiqui, H. L., Khattak, M. I., Ahmad, S. & Parvez, M. (2011b). Acta Cryst. E67, o218-o219.
Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M. & Parvez, M. (2010b). Eur. J. Med. Chem. 45, 698-704.
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Lombardino, J. G., Wiseman, E. H. & Chiaini, J. (1973). J. Med. Chem. 16, 493-496.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Silverstein, F. E., Faich, G., Goldstein, J. L., Simon, L. S., Pincus, T., Whelton, A., Makuch, R., Eisen, G., Agrawal, N. M., Stenson, W. F., Burr, A. M., Zhao, W. W., Kent, J. D., Lefkowith, J. B., Verburg, K. M. & Geis, G. S. (2000). J. Am. Med. Assoc. 284, 1247-1255.
Turck, D., Roth, W. & Busch, U. (1996). Br. J. Rheumatol. 35, 13-16.
Zinnes, H., Lindo, N. A., Sircar, J. C., Schwartz, M. L. & Shavel, J. Jr (1973). J. Med. Chem. 16, 44-48.

organic compounds