3-Chloro-N′-(2-chloro­benzyl­idene)benzohydrazide

Yan Lei; Chuan Fu

doi:10.1107/S1600536811001656

. 2011 Jan 15;67(Pt 2):o410. doi: 10.1107/S1600536811001656

3-Chloro-N′-(2-chlorobenzylidene)benzohydrazide

Yan Lei ^a,^*, Chuan Fu ^a

PMCID: PMC3051651 PMID: 21523081

Abstract

The title compound, C₁₄H₁₀Cl₂N₂O, was prepared from the reaction of 2-chlorobenzaldehyde with 3-chlorobenzohydrazide in methanol. The molecule adopts an E configuration about the methylidene unit and the two aromatic rings form a dihedral angle of 13.8 (2)°. In the crystal, molecules are linked via intermolecular N—H⋯O and C—H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For background to hydrazones, see: El-Asmy et al. (2010 ▶); El-Sherif (2009 ▶); Singh et al. (2009 ▶); El-Tabl et al. (2007 ▶); Lei (2011 ▶). For structures of hydrazone compounds, see: Qiao et al. (2010 ▶); Hussain et al. (2010 ▶); Han & Zhao (2010 ▶); Ahmad et al. (2010 ▶).

Experimental

Crystal data

C₁₄H₁₀Cl₂N₂O
M _r = 293.14
Monoclinic,
a = 13.106 (3) Å
b = 12.588 (3) Å
c = 8.347 (2) Å
β = 97.578 (2)°
V = 1365.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 298 K
0.32 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.865, T _max = 0.873
6893 measured reflections
2954 independent reflections
1936 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.130
S = 1.01
2954 reflections
175 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 global, I. DOI: 10.1107/S1600536811001656/qm2001sup1.cif

e-67-0o410-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001656/qm2001Isup2.hkl

e-67-0o410-Isup2.hkl^{(145KB, 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	0.90 (1)	1.98 (1)	2.854 (2)	164 (2)
C7—H7⋯O1ⁱ	0.93	2.51	3.254 (2)	137 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge financial support from the Chongqing Three Gorges University.

supplementary crystallographic information

Comment

In recent years, much effort has been devoted for developing the hydrazones, due to their biological properties, coordinative capability, and applications in analytical chemistry (El-Asmy et al., 2010; El-Sherif, 2009; Singh et al., 2009; El-Tabl et al., 2007). Recently, a number of hydrazones have been prepared and investigated for their structures (Qiao et al., 2010; Hussain et al., 2010; Han & Zhao, 2010; Ahmad et al., 2010; Lei, 2011). As a continuation of hydrazones, the author reports herein the title new compound.

The molecule of the title compound, Fig. 1, adopts an E configuration about the methylidene unit. The two aromatic rings form a dihedral angle of 13.8 (2)°. In the crystal, the molecules are linked via intermolecular N—H···O and C—H···O hydrogen bonds (Table 1), to form chains at the c-axis direction (Fig. 2).

Experimental

3-Chlorobenzohydrazide (1 mmol, 0.170 g) was dissolved in methanol (50 ml), then 2-chlorobenzaldehyde (1 mmol, 0.140 g) was added into the solution. The reaction mixture was heated under reflux for 1 h and cooled to room temperature. Colourless needle-shaped crystals were formed by slow evaporation of the solvent for a week.