4-(3-Methyl­benzene­sulfonamido)­phenyl 3-methyl­benzene­sulfonate

Al-Najjar, B.O.; Tengku Muhammad, T.S.; Wahab, H.A.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536811054808

Volume 68
Part 2
Page o258
February 2012

Received 30 November 2011
Accepted 20 December 2011
Online 7 January 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
Disorder in main residue
R = 0.031
wR = 0.090
Data-to-parameter ratio = 27.6
Details

4-(3-Methylbenzenesulfonamido)phenyl 3-methylbenzenesulfonate

Belal O. Al-Najjar,^a Tengku Sifzizul Tengku Muhammad,^b,^c Habibah A. Wahab,^a ⁺ Mohd Mustaqim Rosli ^d and Hoong-Kun Fun ^d ^*⁺⁺

^aPharmaceutical Design and Simulation (PhDS) Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia,^bMalaysian Institute of Pharmaceuticals and Nutraceuticals, Ministry of Science, Technology and Innovation, SAINS@USM, No. 10, 11900 Persiaran Bukit Jambul, Pulau Pinang, Malaysia,^cDepartment of Biological Sciences, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

The complete molecule of the title compound, C₂₀H₁₉NO₅S₂, is generated by a crystallographic twofold axis and the O atom and N-H group attached to the central benzene ring are statistically disordered. The dihedral angle between the central and terminal benzene rings is 56.91 (5)° and that between the terminal benzene rings is 29.80 (5)°. In the crystal, N-HO hydrogen bonding links the molecules into sheets lying parallel to the ab plane.

Related literature

For the biological properties of sulfonyl derivatives, see: Supuran et al. (2003). For a related structure, see: Sinha et al. (2011). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₂₀H₁₉NO₅S₂
M_r = 417.48
Monoclinic, C 2/c
a = 14.4352 (1) Å
b = 9.1250 (1) Å
c = 15.4402 (2) Å
= 109.700 (1)°
V = 1914.76 (4) Å³
Z = 4
Mo K radiation
= 0.31 mm^-1
T = 100 K
0.41 × 0.34 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.883, T_max = 0.926
21937 measured reflections
3533 independent reflections
3249 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.090
S = 1.08
3533 reflections
128 parameters
H-atom parameters constrained
_max = 0.46 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O3ⁱ	1.02	1.97	2.9854 (11)	178
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6544 ).

Acknowledgements

HAW gratefully acknowledges the Malaysian Ministry of Science, Technology and Innovation for the synthesis work funded by grant Nos. 311/IFN/69230112 and 304/PFARMASI/650545/I121. HKF thanks USM for the Research University Grant No. 1001/PFIZIK/811160.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sinha, S., Osman, H., Wahab, H. A., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o3275.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Supuran, C. T., Casini, A. & Scozzafava, A. (2003). Med. Res. Rev. 23, 535-558.

organic compounds