(E)-N′-(5-Bromo-2-meth­oxy­benzyl­idene)-2-chloro­benzohydrazide

Xiao-Yan Li

doi:10.1107/S1600536811034623

. 2011 Aug 27;67(Pt 9):o2511. doi: 10.1107/S1600536811034623

(E)-N′-(5-Bromo-2-methoxybenzylidene)-2-chlorobenzohydrazide

Xiao-Yan Li ^a,^*

PMCID: PMC3200979 PMID: 22065403

Abstract

In the title compound, C₁₅H₁₂BrClN₂O₂, the dihedral angle between the two substituted aromatic rings is 77.8 (3)°. The molecule exists in a trans conformation with respect to the methylidene unit. In the crystal structure, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R ₂ ⁸(8) loops.

Related literature

For the crystal structures of some related hydrazone compounds, see: Li (2011a ▶,b ▶); Hashemian et al. (2011 ▶); Lei (2011 ▶); Shalash et al. (2010 ▶). For hydrogen-bond notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₂BrClN₂O₂
M _r = 367.63
Monoclinic,
a = 11.312 (2) Å
b = 7.374 (2) Å
c = 17.979 (3) Å
β = 91.972 (3)°
V = 1499.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.93 mm⁻¹
T = 298 K
0.12 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.720, T _max = 0.821
5249 measured reflections
2451 independent reflections
1877 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.094
S = 1.04
2451 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811034623/hb6337sup1.cif

e-67-o2511-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034623/hb6337Isup2.hkl

e-67-o2511-Isup2.hkl^{(120.4KB, 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⋯O2ⁱ	0.89 (1)	1.99 (1)	2.882 (4)	175 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges the Zibo Vocational Institute for supporting this work.

supplementary crystallographic information

Comment

In the last few years, hydrazones have been attracted much attention for their crystal structures (e.g. Li, 2011a; Hashemian et al., 2011; Lei, 2011; Shalash et al., 2010). The author reports herein the crystal structure of the title new hydrazone compound, (I).

In the title compound, Fig. 1, the dihedral angle between the two substituted aromatic rings is 77.8 (3)°. The molecule exists in a trans configuration with respect to the methylidene unit. The bond values are comparable to those observed in a similar compound the author reported recently (Li, 2011b). In the crystal structure, adjacent two molecules are linked through two intermolecular N—H···O hydrogen bonds (Table 1), forming a dimer (Fig. 2).

Experimental

A mixture of 2-chlorobenzhydrazide (0.171 g, 1 mmol) and 5-bromo-2-methoxybenzaldehyde (0.215 g, 1 mmol) in 30 ml of ethanol containing few drops of acetic acid was refluxed for about 1 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from methanol. Colorless blocks of (I) were obtained by slow evaporation of the solution.