(E)-3-(3-Chloro­phen­yl)-N-(4-hy­droxy-3-meth­oxy­benz­yl)acryl­amide

Xia, L.-Y.; Wang, W.-L.; Huang, Y.-L.; Shan, S.

doi:10.1107/S1600536810022713

Volume 66
Part 7
Page o1700
July 2010

Received 11 June 2010
Accepted 13 June 2010
Online 18 June 2010

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.036
wR = 0.083
Data-to-parameter ratio = 14.2
Details

(E)-3-(3-Chlorophenyl)-N-(4-hydroxy-3-methoxybenzyl)acrylamide

Liang-You Xia,^a Wen-Long Wang,^b Yan-Lan Huang ^b and Shang Shan ^b ^*

^aDepartment of Chemistry, Zunyi Normal College, People's Republic of China, and ^bCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, People's Republic of China
Correspondence e-mail: shanshang@mail.hz.zj.cn

In the title compound, C₁₇H₁₆ClNO₃, the 4-hydroxy-3-methoxybenzyl group is planar [maximum atomic deviation = 0.0138 (16) Å] and is nearly perpendicular to the chlorobenzene ring, making a dihedral angle of 84.67 (4)°. The chlorobenzene and amide groups are located on the opposite sides of the C=C bond, showing an E configuration. The relatively long C=O bond distance of 1.2364 (19) Å and the short C-N bond distance of 1.341 (2) Å suggest electron delocalization in the amide fragment. Intermolecular O-HO, N-HO and weak C-HO hydrogen bonding is present in the crystal structure.

Related literature

The title compound is a derivative of capsaicin. For the biological activity of capsaicin, see: Kaga et al. (1989). For a related structure, see: Huang et al. (2010). For electron delocalization in amide groups, see: Xia et al. (2009).

Experimental

Crystal data

C₁₇H₁₆ClNO₃
M_r = 317.76
Monoclinic, P 2₁ /c
a = 9.036 (3) Å
b = 14.972 (5) Å
c = 11.768 (4) Å
= 95.047 (5)°
V = 1585.9 (9) Å³
Z = 4
Mo K radiation
= 0.25 mm^-1
T = 294 K
0.40 × 0.38 × 0.36 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
7733 measured reflections
2848 independent reflections
1680 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.083
S = 0.87
2848 reflections
201 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO3ⁱ	0.86	2.12	2.960 (2)	165
O3-H3AO1ⁱⁱ	0.82	1.84	2.6491 (18)	172
C2-H2O1ⁱⁱⁱ	0.93	2.41	3.298 (2)	161
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y, -z+1.

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2783 ).

Acknowledgements

The work was supported by the Natural Science Foundation of Zhejiang Province, China (No. M203027).

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Huang, Y.-L., Wang, W.-L. & Shan, S. (2010). Acta Cryst. E66, o877.
Kaga, H., Miura, M. & Orito, K. A. (1989). J. Org. Chem. 54, 3477-3478.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xia, L.-Y., Wang, W.-L., Wang, S.-H., Huang, Y.-L. & Shan, S. (2009). Acta Cryst. E65, o1899.

organic compounds