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

Yu-Min Wang; Zhen-Dong Zhao; Yu-Xiang Chen; Liang-Wu Bi

doi:10.1107/S1600536808039044

. 2008 Nov 26;64(Pt 12):o2459. doi: 10.1107/S1600536808039044

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

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

PMCID: PMC2959971 PMID: 21581427

Abstract

The title compound, C₁₇H₁₇ClN₂O₄, was synthesized from 3,4,5-trimethoxybenzohydrazide and 4-chlorobenzaldehyde. In the crystal structure, packing is stabilized by intramolecular C—H⋯O and intermolecular N—H⋯O and C—H⋯O 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,
a = 5.119 (2) Å
b = 8.210 (4) Å
c = 20.276 (9) Å
α = 101.055 (7)°
β = 92.362 (7)°
γ = 101.459 (7)°
V = 816.9 (7) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.128
S = 1.03
2860 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.39 e Å⁻³

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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039044/at2683sup1.cif

e-64-o2459-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039044/at2683Isup2.hkl

e-64-o2459-Isup2.hkl^{(140.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.86	2.18	2.943 (3)	147
C8—H8C⋯O4	0.96	2.26	2.896 (4)	123
C11—H11⋯O1ⁱ	0.93	2.43	3.145 (3)	134
C16—H16⋯O1ⁱⁱ	0.93	2.57	3.368 (3)	144

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

3,4,5-Trimethoxybenzohydrazide and their deviatives show moderate fungicidal and anti-bacterial activities (Gardner et al., 1991). The antibacterial activity of formylhydrazines and formylhydrazones has been reported by Labouta et al. (1989). Many derivatives of formylhydrazines have interesting biological properties. So we synthesized several derivatives of 3,4,5-trimethoxybenzohydrazide. In our previous paper we have reported the crystal structure of (E)—N'-(2-hydroxybenzylidene)-3,4,5-trimethoxybenzohydrazide (Wang et al., 2008). Now we synthesized the title compound (I) and report here its crystal structure.

The molecular structure of (I) is shown in Fig. 1. All bond lengths and angles in (I) are normal (Allen et al., 1987). In the crystal structure, there exist intramolecular C—H···O, and intermolecular N—H···O and C—H···O hydrogen bonding interactions (Table 1, Fig. 2).

Experimental

An ethanol solution (50 ml) of 3,4,5-trimethoxybenzohydrazide (0.01 mol) and 4-chlorobenzaldehyde (0.01 mol) was refluxed and stirred for 2 h; the mixture was cooled and the resulting solid product, (I), was collected by filtration. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in THF.