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Volume 70 
Part 1 
Pages o6-o7  
January 2014  

Received 4 September 2013
Accepted 25 November 2013
Online 4 December 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.104
Data-to-parameter ratio = 14.2
Details
Open access

4-Methyl-N-(4-methyl­phenyl­sulfon­yl)-N-[4-(4-methyl­phen­yl)-1,3-thia­zol-2-yl]benzene­sulfonamide

aFacultad de Química, Universidad, Autónoma de Yucatán, Calle 41 No. 421, Col. Industrial, CP 97150, Mérida, Yucatán, Mexico, and bInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, DF 04510, Mexico
Correspondence e-mail: gmiron@uady.mx

There are two independent mol­ecules in the asymmetric unit of the title compound, C24H22N2O4S3. In each, the sulfonamide N atoms reveal nearly a trigonal-planar geometry with two S atoms of the O=S=O groups and one C atom of the thia­zole ring; the angles around the N atoms are between 117.00 (13) and 123.86 (9)°. The methyl­phenyl­sulfonyl groups are in anti conformations, forming dihedral angles of 78.00 (7)/72.53 (5) and 77.09 (6)/71.50 (7)° with the trigonal S-N-S planes in the two mol­ecules. The thia­zole groups are rotated around the C-N bonds and are almost perpendicular to the S-N-S plane [dihedral angles of 78.00 (7)/72.53 (5) and 77.09 (6)/71.50 (7)°]. In the crystal, pairs of C-H...O inter­actions, with the O atoms of the sulfonamide groups as acceptors, link each of the independent mol­ecules into inversion dimers.

Related literature

For bioactive sulfonamide compounds, see: Annadurai et al. (2012[Annadurai, S., Martinez, R., Canney, D. J., Eidem, T., Dunman, P. M. & Abou-Gharbia, M. (2012). Bioorg. Med. Chem. Lett. 22, 7719-7725.]); Farag et al. (2012[Farag, A. A., Abd-Alrahman, S. N., Ahmed, G. F., Ammar, R. M., Ammar, Y. A. & Abbas, S. Y. (2012). Arch. Pharm. Chem. Life Sci. 345, 703-712.]); Xiao-Long et al. (2009[Xiao-Long, Q., Guideng, L., Guikai, W., Jiewen, Z., Longen, Z., Phang-Lang, C., Richard, C. A. & Wen-Hwa, L. (2009). J. Med. Chem. 52, 1757-1767.]).

[Scheme 1]

Experimental

Crystal data
  • C24H22N2O4S3

  • Mr = 498.61

  • Triclinic, [P \overline 1]

  • a = 8.3322 (2) Å

  • b = 12.0630 (3) Å

  • c = 23.5756 (6) Å

  • [alpha] = 84.615 (1)°

  • [beta] = 87.022 (1)°

  • [gamma] = 85.482 (1)°

  • V = 2349.46 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 298 K

  • 0.44 × 0.38 × 0.28 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 18770 measured reflections

  • 8539 independent reflections

  • 6755 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.104

  • S = 0.98

  • 8539 reflections

  • 602 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C29-H29B...O3i 0.96 2.54 3.148 (3) 122
C50-H50C...O5ii 0.96 2.47 3.397 (3) 162
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2458 ).


Acknowledgements

This work was funded by PIFI-2011. The authors from the Universidad Autónoma de Yucatán are grateful to the Instituto de Química, Universidad Nacional Autónoma de México, for permission to the perform the X-ray analysis. We thank Br Hector Peniche Pavia for his participation in the synthetic procedure.

References

Annadurai, S., Martinez, R., Canney, D. J., Eidem, T., Dunman, P. M. & Abou-Gharbia, M. (2012). Bioorg. Med. Chem. Lett. 22, 7719-7725.  [CrossRef] [ChemPort] [PubMed]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farag, A. A., Abd-Alrahman, S. N., Ahmed, G. F., Ammar, R. M., Ammar, Y. A. & Abbas, S. Y. (2012). Arch. Pharm. Chem. Life Sci. 345, 703-712.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Xiao-Long, Q., Guideng, L., Guikai, W., Jiewen, Z., Longen, Z., Phang-Lang, C., Richard, C. A. & Wen-Hwa, L. (2009). J. Med. Chem. 52, 1757-1767.  [Web of Science] [PubMed]


Acta Cryst (2014). E70, o6-o7   [ doi:10.1107/S1600536813032145 ]

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