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Volume 69 
Part 11 
Page o1700  
November 2013  

Received 14 October 2013
Accepted 16 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 290 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.149
Data-to-parameter ratio = 14.7
Details
Open access

N-[(1,3-Benzodioxol-5-yl)meth­yl]benzene­sulfonamide: an analogue of capsaicin

aDepartment of Physics, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, and bDepartment of Pharmacy, Universidade de São Paulo, 05508-000 São Paulo, SP, Brazil
Correspondence e-mail: stellamaganhi@gmail.com

The title compound, C14H13NO4S, an analogue of capsaicin, differs from the latter by having a 1,3-benzodioxole ring rather than a 2-meth­oxy­phenol moiety, and having a benzene­sulfonamide group instead of an aliphatic amide chain. The five-membered ring is in an envelope conformation with the methyl­ene C atom lying 0.221 (6) Å out of the plane formed by the other four atoms. The dihedral angle between the phenyl ring and the mean plane of the 1,3-benzodioxole fused-ring system is 84.65 (4)°. In the crystal, mol­ecules aggregate into supra­molecular layers in the ac plane through C-H...O, N-H...O and C-H...[pi] inter­actions.

Related literature

For background and the biological activity of capsaicin, see: Lee et al. (2011[Lee, M., Kim, C., Kim, I. & Kim, Y. (2011). Phytother. Res. 25, 935-939.]); Malagarie-Cazenave et al. (2011[Malagarie-Cazenave, S., Olea-Herrero, N., Vara, D., Morell, C. & Díaz-Laviada, I. (2011). Cytokine, 54, 330-337.]). For the synthesis and cytoxicity of the title compound, see: De Sá-Junior et al. (2013[De Sá-Junior, P. L., Ferreira, A. K., Pasqualoto, K. F. M., Tavares, M. T., Damiao, M. C. F. C. B., Azevedo, R. A., Camara, D. A. D., Pereira, A., Souza, D. M. & Parise-Filho, R. (2013). Toxicol. Appl. Pharmacol. 266, 385-398.]). For ring conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13NO4S

  • Mr = 291.32

  • Orthorhombic, P b c a

  • a = 18.0158 (4) Å

  • b = 5.9346 (1) Å

  • c = 25.5480 (8) Å

  • V = 2731.51 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 290 K

  • 0.25 × 0.22 × 0.20 mm

Data collection
  • Nonius KappaCCD diffractometer with Bruker APEXII CCD areadetector

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.930, Tmax = 0.948

  • 2652 measured reflections

  • 2652 independent reflections

  • 1860 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.149

  • S = 1.04

  • 2652 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2-C7 and C9-C14 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2i 0.99 2.00 2.945 (3) 157
C14-H14...O1ii 0.93 2.59 3.486 (3) 161
C10-H10...Cg1iii 0.93 2.74 3.563 (3) 147
C8-H8B...Cg2iv 0.97 2.82 3.511 (3) 129
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (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.]); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010[ChemAxon (2010). Marvinsketch. http://www.chemaxon.com.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5268 ).


Acknowledgements

We thank FAPESP (grant no. 2012/22524-9), the São Paulo Research Foundation (SMH), CNPq and CAPES for financial support.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
ChemAxon (2010). Marvinsketch. http://www.chemaxon.com.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
De Sá-Junior, P. L., Ferreira, A. K., Pasqualoto, K. F. M., Tavares, M. T., Damiao, M. C. F. C. B., Azevedo, R. A., Camara, D. A. D., Pereira, A., Souza, D. M. & Parise-Filho, R. (2013). Toxicol. Appl. Pharmacol. 266, 385-398.  [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Lee, M., Kim, C., Kim, I. & Kim, Y. (2011). Phytother. Res. 25, 935-939.  [CrossRef] [ChemPort] [PubMed]
Malagarie-Cazenave, S., Olea-Herrero, N., Vara, D., Morell, C. & Díaz-Laviada, I. (2011). Cytokine, 54, 330-337.  [Web of Science] [ChemPort] [PubMed]
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1700  [ doi:10.1107/S1600536813028481 ]

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