2,3-Dimethyl-N-[(E)-2,4,5-trimeth­oxy­benzyl­idene]aniline

Hussain, A.; Tahir, M.N.; Tariq, M.I.; Ahmad, S.; Asiri, A.M.

doi:10.1107/S1600536810025894

Volume 66
Part 8
Page o1953
August 2010

Received 29 June 2010
Accepted 1 July 2010
Online 7 July 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.045
wR = 0.139
Data-to-parameter ratio = 19.4
Details

2,3-Dimethyl-N-[(E)-2,4,5-trimethoxybenzylidene]aniline

Abid Hussain,^a M. Nawaz Tahir,^b ^* Muhammad Ilyas Tariq,^c Shahbaz Ahmad ^c and Abdullah M. Asiri ^d

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan,^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan,^cDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^dChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia
Correspondence e-mail: dmntahir_uos@yahoo.com

In the title compound, C₁₈H₂₁NO₃, the C=N bond has a trans conformation and the benzene rings are oriented at a dihedral angle of 61.32 (6)°. The C atoms of the three methoxy groups are all roughly coplanar with their attached ring [deviations = 0.219 (2), -0.097 (2) and -0.137 (2) Å]. In the crystal, a weak C-H [pi] interaction may help to establish the packing.

Related literature

For background information on Schiff bases and related crystal structures, see: Tahir et al. (2010a,b); Tariq et al. (2010).

Experimental

Crystal data

C₁₈H₂₁NO₃
M_r = 299.36
Triclinic, $[P \overline 1]$
a = 7.0040 (2) Å
b = 11.0396 (4) Å
c = 11.1585 (4) Å
= 73.941 (1)°
= 76.022 (2)°
= 82.079 (1)°
V = 802.24 (5) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 296 K
0.32 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.980, T_max = 0.985
13855 measured reflections
3957 independent reflections
2935 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.139
S = 1.07
3957 reflections
204 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
C16-H16BCg1ⁱ	0.96	2.99	3.5694 (19)	120
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5535 ).

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Ather, A. Q. (2010a). Acta Cryst. E66, o1562.
Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Ather, A. Q. (2010b). Acta Cryst. E66, o1817.
Tariq, M. I., Ahmad, S., Tahir, M. N., Sarfaraz, M. & Hussain, I. (2010). Acta Cryst. E66, o1561.

organic compounds