4-Chloro-2-[(E)-({4-[N-(3,4-dimethyl­isoxazol-5-yl)sulfamo­yl]phen­yl}iminio)meth­yl]phenolate

Shad, H.A.; Chohan, Z.H.; Tahir, M.N.; Khan, I.U.

doi:10.1107/S1600536808005321

Volume 64
Part 3
Page o635
March 2008

Received 1 February 2008
Accepted 25 February 2008
Online 27 February 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.128
Data-to-parameter ratio = 13.8
Details

4-Chloro-2-[(E)-({4-[N-(3,4-dimethylisoxazol-5-yl)sulfamoyl]phenyl}iminio)methyl]phenolate

Hazoor A. Shad,^a Zahid H. Chohan,^a M. Nawaz Tahir ^b and Islam Ullah Khan ^c ^*

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan,^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^cGovernment College University, Department of Chemistry, Lahore, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

The title compound, C₁₈H₁₆ClN₃O₄S, is a Schiff base ligand in which the H atom of the hydroxy group has moved to the N atom of the imine group, resulting in a zwitterion. The structure is stabilized by an intramolecular (N-HO) and five intermolecular (C-HO, C-HN and N-HO) hydrogen bonds. The molecules are linked to each other by hydrogen bonds and form a three-dimensional polymeric network. In addition, the aromatic rings are also involved in [pi] - [pi] interactions [centroid-centroid distance between aromatic rings = 3.7525 (11) Å].

Related literature

For related literature, see: Chatterjee et al. (1982); Chohan et al. (2008); Hämäläinen et al. (1986); Nishimori et al. (2005).

Experimental

Crystal data

C₁₈H₁₆ClN₃O₄S
M_r = 405.85
Monoclinic, P 2₁ /n
a = 15.1871 (6) Å
b = 7.2555 (3) Å
c = 16.6267 (7) Å
= 94.081 (2)°
V = 1827.45 (13) Å³
Z = 4
Mo K radiation
= 0.35 mm^-1
T = 296 (2) K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.886, T_max = 0.935
18429 measured reflections
4669 independent reflections
3443 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.127
S = 1.04
3443 reflections
250 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.38 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.87 (2)	1.85 (2)	2.574 (2)	140 (2)
C7-H7N3ⁱ	0.93	2.54	3.429 (3)	161
C12-H12O2ⁱ	0.93	2.59	3.391 (3)	145
C17-H17CO3ⁱⁱ	0.96	2.57	3.516 (3)	168
C17-H17BO1ⁱⁱⁱ	0.96	2.38	3.276 (3)	156
N2-H2O1ⁱⁱⁱ	0.79 (2)	2.06 (2)	2.846 (2)	173 (2)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); 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) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2068 ).

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer.

References

Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsion, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsion, USA.
Chatterjee, C., Dattagupta, J. K. & Saha, N. N. (1982). Acta Cryst. B38, 1845-1847.
Chohan, Z. H., Shad, H. A., Tahir, M. N. & Khan, I. U. (2008). Acta Cryst. E64 Submitted.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Hämäläinen, R., Lehtinen, M. & Turpeinen, U. (1986). Arch. Pharm. 319, 415-420.
Nishimori, I., Vullo, D., Innocenti, A., Scozzafava, A., Mastrolorenz, A. & Supuran, C. T. (2005). Bioorg. Med. Chem. Lett. 15, 3828-3833.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds