N-(4-Chloro­benzyl­idene)-4-methoxy­aniline

Ren, X.-Y.; Ding, Y.-F.; Jian, F.-F.

doi:10.1107/S1600536808026111

Volume 64
Part 9
Page o1793
September 2008

Received 27 July 2008
Accepted 13 August 2008
Online 20 August 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.035
wR = 0.089
Data-to-parameter ratio = 18.2
Details

N-(4-Chlorobenzylidene)-4-methoxyaniline

Xiao-Yan Ren,^a Yu-Feng Ding ^b and Fang-Fang Jian ^a ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China, and ^bThe 7th Middle School, Weifang 261061, People's Republic of China
Correspondence e-mail: ffjian2008@163.com

The title compound, C₁₄H₁₂ClNO, was prepared by the reaction of 4-methoxyaniline and 4-chlorobenzaldehyde in ethanol at 367 K. The molecule is almost planar, with a dihedral angle between the two benzene rings of 9.1 (2)° and an r.m.s. deviation from the mean plane through all non-H atoms in the molecule of 0.167 Å.

Related literature

For applications of Schiff base compounds, see: Deschamps et al. (2003); Rozwadowski et al. (1999); Tarafder et al. (2000). For a related structure, see: Jian et al. (2006).

Experimental

Crystal data

C₁₄H₁₂ClNO
M_r = 245.70
Orthorhombic, P n a 2₁
a = 6.1055 (9) Å
b = 7.3392 (11) Å
c = 27.469 (4) Å
V = 1230.9 (3) Å³
Z = 4
Mo K radiation
= 0.29 mm^-1
T = 293 (2) K
0.20 × 0.15 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
7232 measured reflections
2806 independent reflections
2092 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.088
S = 1.01
2806 reflections
154 parameters
1 restraint
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 1450 Friedel pairs
Flack parameter: -0.01 (7)

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2527 ).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deschamps, P., Kulkarni, P. P. & Sarkar, B. (2003). Inorg. Chem., 42, 7366-7368.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Jian, F.-F., Zhuang, R.-R., Wang, K.-F., Zhao, P.-S. & Xiao, H.-L. (2006). Acta Cryst. E62, o3198-o3199.
Rozwadowski, Z., Majewski, E., Dziembowska, T. & Hansen, P. E. (1999). J. Chem. Soc. Perkin Trans. 2, pp. 2809-2817.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tarafder, M. T. H., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem. 25, 456-460.

organic compounds