N′-(2-Chloro­benzyl­idene)-4-nitro­benzohydrazide

Chun-Bao Tang

doi:10.1107/S1600536811055589

. 2012 Jan 11;68(Pt 2):o335. doi: 10.1107/S1600536811055589

N′-(2-Chlorobenzylidene)-4-nitrobenzohydrazide

Chun-Bao Tang ^a,^*

PMCID: PMC3275020 PMID: 22346965

Abstract

In the title compound, C₁₄H₁₀ClN₃O₃, the dihedral angle between the benzene rings is 6.64 (13)°. In the crystal, molecules are linked through N—H⋯O hydrogen bonds, forming chains running along the c axis direction.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶, 2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₀ClN₃O₃
M _r = 303.70
Monoclinic,
a = 11.2332 (18) Å
b = 13.3778 (18) Å
c = 8.9770 (16) Å
β = 90.408 (2)°
V = 1349.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.949, T _max = 0.957
10640 measured reflections
2931 independent reflections
1882 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.146
S = 1.03
2931 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055589/su2353sup1.cif

e-68-0o335-sup1.cif^{(15.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055589/su2353Isup2.hkl

e-68-0o335-Isup2.hkl^{(143.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811055589/su2353Isup3.cml

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	0.89 (1)	2.06 (1)	2.915 (3)	160 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the Jiaying University research fund is gratefully acknowledged.

supplementary crystallographic information

Comment

Hydrazone compounds have received much attention in biological and structural chemistry in the last few years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010; Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010). As a continuation of our work on the structural study on such compounds (Tang, 2010, 2011), we reports herein on the crystal structure of the title new hydrazone compound.

In the molecule of the title compound (Fig. 1), the dihedral angle between the two benzene rings is 6.64 (13)°. Bond lengths in the compound are normal (Allen et al., 1987) and comparable to those in the similar compounds (Tang, 2010; Tang, 2011).

In the crystal, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains running along the c axis direction (Fig. 2).

Experimental

2-Chlorobenzaldehyde (0.1 mmol, 14.1 mg) and 4-nitrobenzohydrazide (0.1 mmol, 18.2 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear yellow solution. Yellow needle-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.