3-Chloro-N′-(2,4-dichloro­benzyl­idene)benzohydrazide

Yan Lei

doi:10.1107/S1600536810051913

. 2010 Dec 18;67(Pt 1):o162. doi: 10.1107/S1600536810051913

3-Chloro-N′-(2,4-dichlorobenzylidene)benzohydrazide

Yan Lei ^a,^*

PMCID: PMC3050239 PMID: 21522669

Abstract

The title compound, C₁₄H₉Cl₃N₂O, adopts an E configuration about the methylidene unit and the two aromatic rings form a dihedral angle of 6.6 (2)°. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, forming C(4) chains propagating in [001]. C—H⋯O interactions reinforce the chains.

Related literature

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

Experimental

Crystal data

C₁₄H₉Cl₃N₂O
M _r = 327.58
Monoclinic,
a = 12.372 (3) Å
b = 14.071 (2) Å
c = 8.332 (2) Å
β = 97.582 (3)°
V = 1437.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.833, T _max = 0.848
7125 measured reflections
3081 independent reflections
1776 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.129
S = 1.02
3081 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.34 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/S1600536810051913/hb5766sup1.cif

e-67-0o162-sup1.cif^{(15.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051913/hb5766Isup2.hkl

e-67-0o162-Isup2.hkl^{(151.2KB, 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)	2.08 (2)	2.900 (3)	152 (3)
C7—H7⋯O1ⁱ	0.93	2.35	3.155 (3)	145

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges financial support from Chongqing Three Gorges University.

supplementary crystallographic information

Comment

Significant attention has been attracted on the hydrazones for 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). 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 6.6 (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 2,4-dichlorobenzaldehyde (1 mmol, 0.174 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.