(E)-4-Meth­oxy-N′-(4-nitro­benzyl­idene)benzohydrazide methanol monosolvate

Hong-Yan Ban

doi:10.1107/S160053681004701X

. 2010 Nov 20;66(Pt 12):o3240. doi: 10.1107/S160053681004701X

(E)-4-Methoxy-N′-(4-nitrobenzylidene)benzohydrazide methanol monosolvate

Hong-Yan Ban ^a,^*

PMCID: PMC3011623 PMID: 21589529

Abstract

The hydrazone molecule of the title compound, C₁₅H₁₃N₃O₄·CH₄O, is nearly planar, with a dihedral angle between the two benzene rings of 1.2 (4)°. The molecule exists in a trans configuration with respect to the central methylidene unit. In the crystal, the benzohydrazide and methanol molecules are linked through intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Ban & Li (2008a ▶,b ▶); Li & Ban (2009a ▶,b ▶); Yehye et al. (2008 ▶); Fun, Patil, Jebas et al., 2008 ▶; Fun, Patil, Rao et al., 2008 ▶; Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O₄·CH₄O
M _r = 331.33
Monoclinic,
a = 6.6482 (14) Å
b = 17.730 (3) Å
c = 13.898 (2) Å
β = 95.004 (3)°
V = 1631.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.20 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T _min = 0.980, T _max = 0.983
12876 measured reflections
3466 independent reflections
1184 reflections with I > 2σ(I)
R _int = 0.115

Refinement

R[F ² > 2σ(F ²)] = 0.081
wR(F ²) = 0.204
S = 0.94
3466 reflections
222 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.27 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 datablocks global, I. DOI: 10.1107/S160053681004701X/rz2522sup1.cif

e-66-o3240-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004701X/rz2522Isup2.hkl

e-66-o3240-Isup2.hkl^{(170KB, 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
O5—H5⋯O3	0.82	2.03	2.812 (4)	159
O5—H5⋯N2	0.82	2.61	3.194 (4)	129
N3—H3A⋯O5ⁱ	0.90 (1)	2.02 (2)	2.900 (4)	166 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges financial support by the Research Foundation of Liaoning Province (grant No. 2008470).

supplementary crystallographic information

Comment

Hydrazone compounds derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a large number of hydrazone compounds have been synthesized and structurally characterized (Yehye et al., 2008; Fun, Patil, Jebas et al., 2008; Fun, Patil, Rao et al., 2008; Yang et al., 2008; Ejsmont et al., 2008). Recently, we have reported a few such compounds (Ban & Li, 2008a,b; Li & Ban, 2009a,b). Herein the crystal structure of the title new compound is reported.

The asymmetric unit of the title compound consists of a hydrazone molecule and a methanol molecule (Fig. 1). The hydrazone molecule is nearly planar, the dihedral angle between the two benzene rings being 1.2 (4)°. The molecule exists in a trans configuration with respect to the central methylidene unit. In the crystal structure, the hydrazone molecules and the methanol molecules are linked through intermolecular O—H···O, O—H···N and N—H···O hydrogen bonds (Table 1), forming chains along the a axis (Fig. 2).

Experimental

The title compound was prepared by refluxing 4-nitrobenzaldehyde (1.0 mol) with 4-methoxybenzohydrazide (1.0 mol) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. A colourless solid product was filtered, and washed three times with methanol. Colourless block-shaped crystals of the title compound were obtained from a methanol solution by slow evaporation in air.