4-[(2-Hy­droxy­benzyl­idene)amino]-N-(5-methyl­isoxazol-3-yl)benzene­sulfonamide: a monoclinic polymorph

Ebenezer, S.; Muthiah, P.T.

doi:10.1107/S1600536810036585

Volume 66
Part 10
Page o2574
October 2010

Received 25 August 2010
Accepted 13 September 2010
Online 18 September 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.049
wR = 0.115
Data-to-parameter ratio = 13.0
Details

4-[(2-Hydroxybenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamide: a monoclinic polymorph

Samuel Ebenezer ^a and Packianathan Thomas Muthiah ^a ^*

^aSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India
Correspondence e-mail: tommtrichy@yahoo.co.in

The title compound, C₁₇H₁₅N₃O₄S, is a monoclinic polymorph with space group P2₁/c of the previously reported triclinic form in P $[\overline{1}]$ [Subashini et al. (2009). J. Chem. Crystallogr. 39, 112-116]. In both polymorphs, intramolecular O-HN hydrogen bonds and dimer formation via a pair of intermolecular N-HN hydrogen bonds with an R₂²(8) motif are observed. The two polymorphs differ in the next level of supramolecular organization involving C-HO hydrogen bonds with varied packing and different conformations.

Related literature

For the biological relevance of sulfonamide drugs and their Schiff base derivatives, see: Genc et al. (2008); Supuran et al. (1997). For the triclinic polymorph of the title compound, see: Subashini et al. (2009). For $[R_{2}^{2}]$ (8) ring motifs in sulfonamides, see: Adsmond & Grant (2001). For conformational studies on sulfonamides, see: Kálmán et al. (1981).

Experimental

Crystal data

C₁₇H₁₅N₃O₄S
M_r = 357.39
Monoclinic, P 2₁ /c
a = 7.0374 (1) Å
b = 17.9244 (3) Å
c = 14.5175 (3) Å
= 112.962 (1)°
V = 1686.15 (5) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 293 K
0.25 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.947, T_max = 0.957
14935 measured reflections
2953 independent reflections
2198 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.115
S = 1.06
2953 reflections
227 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.82	1.88	2.606 (3)	147
N2-H2AN3ⁱ	0.86	2.24	2.898 (4)	134
C10-H10O1ⁱⁱ	0.93	2.53	3.313 (3)	141
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2595 ).

Acknowledgements

The authors thank the DST-India (FIST programme) for the use of diffractometer at the School of Chemistry, Bharathidasan University.

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.
Genc, Y., Ozkanca, R. & Bekdemir, Y. (2008). Ann. Clin. Microbiol. Antimicrob. 7, 1-6.
Kálmán, A., Czugler, M. & Argay, Gy. (1981). Acta Cryst. B37, 868-877.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Subashini, A., Hemamalini, M., Muthiah, P. T., Bocelli, G. & Cantoni, A. (2009). J. Chem. Crystallogr. 39, 112-116.
Supuran, C. T., Scozzafava, A., Popescu, A., Bobes-Tureac, R., Banciu, A., Bobes-Tureac, G. & Bamciu, M. D. (1997). Eur. J. Med. Chem. 32, 445-452.