3-Chloro-N′-(4-hy­droxy-3-nitro­benzyl­idene)benzohydrazide methanol disolvate

Zhen Zhang

doi:10.1107/S1600536811021568

. 2011 Jun 11;67(Pt 7):o1630. doi: 10.1107/S1600536811021568

3-Chloro-N′-(4-hydroxy-3-nitrobenzylidene)benzohydrazide methanol disolvate

Zhen Zhang ^a,^*

PMCID: PMC3151852 PMID: 21837036

Abstract

In the title compound, C₁₄H₁₀ClN₃O₄·2CH₄O, the main molecule is in an E configuration with respect to the methylidene unit. The dihedral angle between the mean planes of the two benzene rings is 1.9 (3)°. In the crystal, intermolecular N—H⋯O, O—H⋯O and bifurcated O—H⋯(O, O) hydrogen bonds link the components into sheets parallel to (100). An intramolecular O—H⋯O hydrogen bond is also present.

Related literature

For the biological applications of hydrazone compounds, see: Ajani et al. (2010 ▶); Avaji et al. (2009 ▶); Fan et al. (2010 ▶); Rasras et al. (2010 ▶). For related hydrazone structures, see: Zhang (2011a ▶,b ▶); Ahmad et al. (2010 ▶); Ban (2010 ▶); Ji & Lu (2010 ▶); Shalash et al. (2010 ▶).

Experimental

Crystal data

C₁₄H₁₀ClN₃O₄·2CH₄O
M _r = 383.78
Monoclinic,
a = 7.626 (2) Å
b = 18.846 (5) Å
c = 12.739 (3) Å
β = 94.689 (4)°
V = 1824.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 298 K
0.23 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.945, T _max = 0.950
7726 measured reflections
3695 independent reflections
1842 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.208
S = 1.06
3695 reflections
243 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021568/lh5265sup1.cif

e-67-o1630-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021568/lh5265Isup2.hkl

e-67-o1630-Isup2.hkl^{(181.2KB, 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
O3—H3A⋯O1	0.82	1.96	2.618 (4)	137
O3—H3A⋯O5	0.82	2.26	2.896 (4)	135
O6—H6⋯O5	0.82	1.88	2.700 (5)	179
N3—H3⋯O6ⁱ	0.89 (1)	1.99 (2)	2.834 (4)	158 (4)
O5—H5⋯O4ⁱⁱ	0.82	1.96	2.779 (4)	173

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

Acknowledgments

The author thanks the Experimental Center of Linyi University for supporting this work.

supplementary crystallographic information

Comment

Hydrazone compounds have received much attention due to their potential applications in biological chemistry (Ajani et al., 2010; Avaji et al., 2009; Fan et al., 2010; Rasras et al., 2010). As a continuation of this work on hydrazone compounds the structure of the title compound is reported herein.

The asymmetric unit of title compound, Fig. 1, contains a hydrazone molecule and two methanol molecules. The hydrazone molecule assumes an E configuration with respect to the methylidene unit. The dihedral angle between the mean planes of the two benzene rings is 1.9 (3)°. The bond lengths are comparable to those observed in similar hydrazone compounds (Zhang, 2011a,b; Ahmad et al., 2010; Ban, 2010; Ji & Lu, 2010; Shalash et al., 2010). In the crystal, intermolecular N—H···O and O—H···O hydrogen bonds link the components into two dimensional sheets parallel to (100). An intramolecular O-H···O hydrogen bond is also present (Table 1, Fig. 2).

Experimental

A methanol solution (50 ml) of 3-chlorobenzohydrazide (0.01 mol) and 4-hydroxy-3-nitrobenzaldehyde (0.01 mol) was stirred at room temperature for 30 min to give a yellow solution. Yellow block-shaped single crystals suitable for X-ray diffraction were formed by slow evaporation of the solution in air.