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Volume 69 
Part 3 
Page o332  
March 2013  

Received 21 January 2013
Accepted 22 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 290 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.149
Data-to-parameter ratio = 14.3
Details
Open access

N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of capsaicin

aDepartmento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, and bDepartmento de Farmacia, Universidade de São Paulo, 05508-000 São Paulo, SP, Brazil
Correspondence e-mail: stellamaganhi@gmail.com

In the title compound, C16H15NO3, the five-membered 1,3-dioxole ring is in an envelope conformation with the methylene C atom as the flap atom [lying 0.202 (3) Å out of the plane formed by the other four atoms]. The benzene ring makes a dihedral angle of 84.65 (4)° with the best least-squares plane through the 1,3-benzodioxole fused-ring system, which substitutes the 2-methoxyphenol moiety in capsaicin. In the crystal, molecules are connected into a zigzag supramolecular chain along the c-axis direction by N-H...O hydrogen bonds. These chains are connected into a layer in the ac plane by C-H...[pi] interactions.

Related literature

For the biological activity of capsaicin, see: Okamoto et al. (2011[Okamoto, M., Irii, H., Tahara, Y., Ishii, H., Hirao, A., Udagawa, H., Hiramoto, M., Yasuda, K., Takanishi, A., Shibata, S. & Shimizu, I. (2011). J. Med. Chem. 54, 6295-6304.]). 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
  • C16H15NO3

  • Mr = 269.29

  • Monoclinic, P 21 /c

  • a = 4.9810 (2) Å

  • b = 26.652 (1) Å

  • c = 10.0545 (3) Å

  • [beta] = 92.139 (2)°

  • V = 1333.84 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 290 K

  • 0.33 × 0.24 × 0.16 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: numerical (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.940, Tmax = 0.951

  • 4550 measured reflections

  • 2602 independent reflections

  • 1698 reflections with I > 2[sigma](I)

  • Rint = 0.023

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

  • wR(F2) = 0.149

  • S = 1.03

  • 2602 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C10-C15 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O3i 0.91 2.08 2.958 (2) 162
C7-H7A...Cg1 0.97 2.74 3.603 (3) 149
C16-H16C...Cg2 0.96 2.96 3.829 (2) 151
Symmetry code: (i) [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: TK5191 ).


Acknowledgements

We thank the Brazilian agencies CNPq (140925/2009-0 to SHM), FAPESP and CAPES for financial support. We also thank Professor Carlos A. De Simone for the data collection.

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.  [ISI] [CrossRef] [ChemPort] [details]
Chemaxon (2010). Marvinsketch. http://www.chemaxon.com.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Okamoto, M., Irii, H., Tahara, Y., Ishii, H., Hirao, A., Udagawa, H., Hiramoto, M., Yasuda, K., Takanishi, A., Shibata, S. & Shimizu, I. (2011). J. Med. Chem. 54, 6295-6304.  [ISI] [CrossRef] [ChemPort] [PubMed]
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] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o332  [ doi:10.1107/S1600536813002201 ]

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