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

Maganhi, S.H.; Damião, M.C.F.C.B.; Tavares, M.T.; Parise Filho, R.

doi:10.1107/S1600536813002201

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 (C-C) = 0.003 Å
R = 0.050
wR = 0.149
Data-to-parameter ratio = 14.3
Details

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

Stella H. Maganhi,^a ^* Mariana C. F. C. B. Damião,^b Maurício T. Tavares ^b and Roberto Parise Filho ^b

^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-HO 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). For ring conformational analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₆H₁₅NO₃
M_r = 269.29
Monoclinic, P 2₁ /c
a = 4.9810 (2) Å
b = 26.652 (1) Å
c = 10.0545 (3) Å
= 92.139 (2)°
V = 1333.84 (8) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.940, T_max = 0.951
4550 measured reflections
2602 independent reflections
1698 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.149
S = 1.03
2602 reflections
182 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_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-HA	D-H	HA	DA	D-HA
N1-H1N1O3ⁱ	0.91	2.08	2.958 (2)	162
C7-H7ACg1	0.97	2.74	3.603 (3)	149
C16-H16CCg2	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); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Marvinsketch (Chemaxon, 2010) and publCIF (Westrip, 2010).

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.
Chemaxon (2010). Marvinsketch. http://www.chemaxon.com.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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.
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.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds