4-[(E)-(2-Methoxy­phen­yl)imino­meth­yl]-N,N-dimethyl­aniline

Liu, S.-B.; Bi, C.-F.; Wang, Q.; Zuo, J.; Fan, Y.-H.

doi:10.1107/S1600536810017228

Volume 66
Part 6
Page o1361
June 2010

Received 26 April 2010
Accepted 11 May 2010
Online 15 May 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.043
wR = 0.123
Data-to-parameter ratio = 13.6
Details

4-[(E)-(2-Methoxyphenyl)iminomethyl]-N,N-dimethylaniline

Shan-Bin Liu,^a ^* Cai-Feng Bi,^a Qiang Wang,^a Jian Zuo ^a and Yu-Hua Fan ^a

^aKey Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao, Shandong 266100, People's Republic of China
Correspondence e-mail: bamboo19830406@163.com

In the title compound, C₁₆H₁₈N₂O, the dihedral angle between the benzene rings is 38.5 (2)°. The crystal packing is stabilized by weak C-HN and C-HO interactions and aromatic [pi] - [pi] stacking [centroid-centroid separations = 3.620 (5) and 3.546 (4) Å].

Related literature

For general background to Schiff bases, see: Atwood & Harvey (2001). For a related structure, see: Liu et al. (2009).

Experimental

Crystal data

C₁₆H₁₈N₂O
M_r = 254.32
Orthorhombic, P n a 2₁
a = 15.182 (8) Å
b = 11.756 (6) Å
c = 7.809 (4) Å
V = 1393.8 (13) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 298 K
0.60 × 0.58 × 0.49 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996) T_min = 0.956, T_max = 0.963
6900 measured reflections
2335 independent reflections
1554 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.123
S = 1.01
2335 reflections
172 parameters
1 restraint
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8CN1ⁱ	0.96	2.67	3.620 (5)	170
C4-H4O1ⁱ	0.93	2.64	3.546 (4)	166
Symmetry code: (i) $[-x, -y+2, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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: HB5420 ).

Acknowledgements

The authors acknowledge the National Science Foundation of China for its financial support of this project (grant No. 20971115).

References

Atwood, D. A. & Harvey, M. J. (2001). Chem. Rev. 101, 37-52.
Liu, X.-Y., Fan, Y.-H., Bi, C.-F., Wang, Q. & Gao, Y. (2009). Acta Cryst. E65, o2170.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

organic compounds