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

Ahmad, M.; Siddiqui, H.L.; Ahmad, N.; Aslam, S.; Parvez, M.

doi:10.1107/S160053681203187X

Volume 68
Part 8
Pages o2470-o2471
August 2012

Received 12 July 2012
Accepted 12 July 2012
Online 18 July 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.006 Å
R = 0.049
wR = 0.146
Data-to-parameter ratio = 11.4
Details

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

Matloob Ahmad,^a Hamid Latif Siddiqui,^b ^* Naveed Ahmad,^b Sana Aslam ^b and Masood Parvez ^c

^aDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan,^bInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
Correspondence e-mail: drhamidlatif@hotmail.com

In the title molecule, C₂₀H₁₉FN₄O₃S, the heterocyclic thiazine ring adopts a half-chair conformation with the S atom displaced by 0.668 (4) Å from the mean plane formed by the remaining ring atoms. The mean planes of the benzene and pyrazole rings are inclined with respect to each other at a dihedral angle of 17.4 (3)°. The acetamide chain (O/N/C/C/C) linking the pyrazole and 2-fluorobenzyl rings is essentially planar (r.m.s. deviation = 0.030 Å) and forms dihedral angles with the mean planes of these rings of 78.8 (2) and 78.89 (14)°, respectively. The crystal structure is stabilized by N-HO and C-HO hydrogen-bonding interactions, resulting in a six-membered ring with an R₂¹(6) motif, while C-HO and C-HF hydrogen-bonding interactions result in chains of molecules lying along the c axis in a zigzag fashion.

Related literature

For biological activities of benzothiazine derivatives, see: Turck et al. (1996); Silverstein et al. (2000); Lombardino et al. (1973); Zinnes et al. (1973); Ahmad, Siddiqui, Ahmad et al. (2010); Ahmad, Siddiqui, Zia-ur-Rehman & Parvez (2010). For related crystal structures, see: Siddiqui et al. (2008, 2009). For graph-set notations, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₀H₁₉FN₄O₃S
M_r = 414.45
Orthorhombic, P n a 2₁
a = 27.4331 (15) Å
b = 7.4519 (5) Å
c = 9.2598 (6) Å
V = 1893.0 (2) Å³
Z = 4
Cu K radiation
= 1.88 mm^-1
T = 173 K
0.12 × 0.06 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.806, T_max = 0.912
17539 measured reflections
3009 independent reflections
2730 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.146
S = 1.09
3009 reflections
264 parameters
1 restraint
H-atom parameters constrained
_max = 1.05 e Å^-3
_min = -0.45 e Å^-3
Absolute structure: Flack (1983), 1207 Friedel pairs
Flack parameter: 0.05 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4AO3ⁱ	0.88	2.09	2.940 (5)	162
C3-H3O2ⁱⁱ	0.95	2.50	3.366 (6)	152
C14-H14AF1ⁱⁱⁱ	0.99	2.53	3.202 (6)	125
C12-H12BO3ⁱ	0.99	2.42	3.195 (6)	135
C14-H14BF1	0.99	2.42	2.820 (6)	103
Symmetry codes: (i) $[-x, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, -y-1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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: QM2076 ).

Acknowledgements

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

References

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Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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