(E)-N′-(4-Chloro­benzyl­idene)-3,4,5-trimethoxy­benzohydrazide

Wang, Y.-M.; Zhao, Z.-D.; Chen, Y.-X.; Bi, L.-W.

doi:10.1107/S1600536808039044

Volume 64
Part 12
Page o2459
December 2008

Received 19 November 2008
Accepted 21 November 2008
Online 26 November 2008

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.003 Å
R = 0.046
wR = 0.128
Data-to-parameter ratio = 13.1
Details

(E)-N'-(4-Chlorobenzylidene)-3,4,5-trimethoxybenzohydrazide

Yu-Min Wang,^a Zhen-Dong Zhao,^a ^* Yu-Xiang Chen ^a and Liang-Wu Bi ^a

^aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
Correspondence e-mail: minwangyu@126.com

The title compound, C₁₇H₁₇ClN₂O₄, was synthesized from 3,4,5-trimethoxybenzohydrazide and 4-chlorobenzaldehyde. In the crystal structure, packing is stabilized by intramolecular C-HO and intermolecular N-HO and C-HO hydrogen-bonding interactions.

Related literature

For related literature, see: Yang et al. (1996); Nawar et al. (2000); Gardner et al. (1991); Labouta et al. (1989); Wang et al. (2008); Allen et al. (1987).

Experimental

Crystal data

C₁₇H₁₇ClN₂O₄
M_r = 348.78
Triclinic, $[P \overline 1]$
a = 5.119 (2) Å
b = 8.210 (4) Å
c = 20.276 (9) Å
= 101.055 (7)°
= 92.362 (7)°
= 101.459 (7)°
V = 816.9 (7) Å³
Z = 2
Mo K radiation
= 0.26 mm^-1
T = 273 (2) K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.970, T_max = 0.985
4307 measured reflections
2860 independent reflections
2497 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.128
S = 1.03
2860 reflections
218 parameters
H-atom parameters constrained
_max = 0.59 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	0.86	2.18	2.943 (3)	147
C8-H8CO4	0.96	2.26	2.896 (4)	123
C11-H11O1ⁱ	0.93	2.43	3.145 (3)	134
C16-H16O1ⁱⁱ	0.93	2.57	3.368 (3)	144
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+1.

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: AT2683 ).

Acknowledgements

This work was supported by the Natural Science Fund of Jiangsu Province (No. BK2006011).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (1997). SAINT and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.
Gardner, T. S., Weins, R. & Lee, J. (1991). J. Org. Chem. 26, 1514-1530.
Labouta, I. M., Hassan, A. M., Aboulwafa, O. M. & Kader, O. (1989). Monatsh. Chem. 120, 571-574.
Nawar, N. & Hosny, N. M. (2000). Transition Met. Chem. 25, 1-8.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Y.-M., Zhao, Z.-D., Chen, Y.-X. & Bi, L.-W. (2008). Acta Cryst. E64, o1009.
Yang, Z. Y., Yang, R. D. & Yu, K. B. (1996). Polyhedron, 15, 3749-3753.

organic compounds