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Volume 68 
Part 11 
Pages o3164-o3165  
November 2012  

Received 1 October 2012
Accepted 11 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.148
Data-to-parameter ratio = 21.6
Details
Open access

(E)-3-(1,3-Benzodioxol-5-yl)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfonamido]methyl}prop-2-enenitrile

aDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India,bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India,cDepartment of Physics, Ganadipathy Tulsi's Jain Engineering College, Kaniyambadi, Vellore 632 102, India, and dDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
Correspondence e-mail: smurugavel27@gmail.com

In the title compound, C25H20N2O5S, the benzodioxole ring system is essentially planar [maximum deviation = 0.021 (2) Å] and forms dihedral angles of 85.2 (1) and 74.2 (1)°, respectively, with the formyl benzene and sulfonyl-bound benzene rings. In the crystal, C-H...O hydrogen bonds generate C(8) chains along [100] and R33(19) ring motifs. In addition, a weak [pi]-[pi] interaction [centroid-centroid distance = 3.937 (3) Å] is also observed.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988[Korolkovas, A. (1988). In Essentials of Medicinal Chemistry, 2nd ed., pp. 699-716. New York: Wiley.]); Mandell & Sande (1992[Mandell, G. L. & Sande, M. A. (1992). In Goodman and Gilman, The Pharmacological Basis of Therapeutics 2, edited by A. Gilman, T. W. Rall, A. S. Nies & P. Taylor, 8th ed., pp. 1047-1057. Singapore: McGraw-Hill.]). For benzodioxole derivatives, see: Ullrich et al. (2004[Ullrich, T., Baumann, K., Welzenbach, K., Schmutz, S., Camenish, G., Meingassner, J. G. & Weitz-Schmidt, G. (2004). Bioorg. Med. Chem. Lett. 14, 2483-2487.]); Gates & Gillon (1974[Gates, P. S. & Gillon, J. (1974). US Patent No. 3 736 338.]); Arndt & Franke (1977[Arndt, F. & Franke, H. (1977). DE Patent No. 2624822.]); Joshi et al. (2005[Joshi, R., Kumar, M. S., Satyamoorthy, K., Unnikrisnan, M. K. & Mukherjee, T. (2005). J. Agric. Food Chem. 53, 2696-2703.]); Jae et al. (2001[Jae, H.-S., Win, M., von Geldern, T. W., Sorensen, B. K., Chiou, W. J., Nguyen, B., Marsh, K. C. & Opgenorth, T. J. (2001). J. Med. Chem. 44, 3978-3984.]); Leite et al. (2004[Leite, A. C. L., Peixoto da Silva, K., de Souza, I. A., Magali de Araujo, J. & Brondani, D. J. (2004). Eur. J. Med. Chem. 39, 1059-1065.]). For related structures, see: Madhanraj et al. (2011[Madhanraj, R., Murugavel, S., Kannan, D. & Bakthadoss, M. (2011). Acta Cryst. E67, o3511.]); Aziz-ur-Rehman et al. (2010[Aziz-ur-Rehman, Tanveer, W., Akkurt, M., Sattar, A., Abbasi, M. A. & Khan, I. U. (2010). Acta Cryst. E66, o2980.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the Thrope-Ingold effect, see: Bassindale (1984[Bassindale, A. (1984). The Third Dimension in Organic Chemistry. New York: John Wiley and Sons.]).

[Scheme 1]

Experimental

Crystal data
  • C25H20N2O5S

  • Mr = 460.49

  • Monoclinic, P 21 /n

  • a = 8.921 (5) Å

  • b = 10.235 (4) Å

  • c = 25.256 (3) Å

  • [beta] = 93.380 (4)°

  • V = 2302.0 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 293 K

  • 0.23 × 0.21 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.959, Tmax = 0.972

  • 26810 measured reflections

  • 6451 independent reflections

  • 3582 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.148

  • S = 1.01

  • 6451 reflections

  • 299 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 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
C15-H15B...O2i 0.97 2.42 3.282 (3) 148
C23-H23...O1ii 0.93 2.41 3.114 (3) 132
C4-H4...O3iii 0.93 2.59 3.195 (3) 124
Symmetry codes: (i) [-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x, y-1, z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia (1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 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: BT6843 ).


Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Arndt, F. & Franke, H. (1977). DE Patent No. 2624822.
Aziz-ur-Rehman, Tanveer, W., Akkurt, M., Sattar, A., Abbasi, M. A. & Khan, I. U. (2010). Acta Cryst. E66, o2980.  [CSD] [CrossRef] [details]
Bassindale, A. (1984). The Third Dimension in Organic Chemistry. New York: John Wiley and Sons.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Gates, P. S. & Gillon, J. (1974). US Patent No. 3 736 338.
Jae, H.-S., Win, M., von Geldern, T. W., Sorensen, B. K., Chiou, W. J., Nguyen, B., Marsh, K. C. & Opgenorth, T. J. (2001). J. Med. Chem. 44, 3978-3984.  [ISI] [CrossRef] [PubMed] [ChemPort]
Joshi, R., Kumar, M. S., Satyamoorthy, K., Unnikrisnan, M. K. & Mukherjee, T. (2005). J. Agric. Food Chem. 53, 2696-2703.  [ISI] [CrossRef] [PubMed] [ChemPort]
Korolkovas, A. (1988). In Essentials of Medicinal Chemistry, 2nd ed., pp. 699-716. New York: Wiley.
Leite, A. C. L., Peixoto da Silva, K., de Souza, I. A., Magali de Araujo, J. & Brondani, D. J. (2004). Eur. J. Med. Chem. 39, 1059-1065.  [ISI] [CrossRef] [PubMed] [ChemPort]
Madhanraj, R., Murugavel, S., Kannan, D. & Bakthadoss, M. (2011). Acta Cryst. E67, o3511.  [CSD] [CrossRef] [details]
Mandell, G. L. & Sande, M. A. (1992). In Goodman and Gilman, The Pharmacological Basis of Therapeutics 2, edited by A. Gilman, T. W. Rall, A. S. Nies & P. Taylor, 8th ed., pp. 1047-1057. Singapore: McGraw-Hill.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Ullrich, T., Baumann, K., Welzenbach, K., Schmutz, S., Camenish, G., Meingassner, J. G. & Weitz-Schmidt, G. (2004). Bioorg. Med. Chem. Lett. 14, 2483-2487.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3164-o3165   [ doi:10.1107/S1600536812042663 ]

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