(E)-2-Meth­oxy-N′-(4-nitro­benzyl­idene)benzohydrazide

Hong-Yan Ban; Cong-Ming Li

doi:10.1107/S160053680905079X

. 2009 Nov 28;65(Pt 12):o3272. doi: 10.1107/S160053680905079X

(E)-2-Methoxy-N′-(4-nitrobenzylidene)benzohydrazide

Hong-Yan Ban ^a,^*, Cong-Ming Li ^b

PMCID: PMC2972042 PMID: 21578966

Abstract

In the title compound, C₁₅H₁₃N₃O₄, the molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the two benzene rings is 6.8 (2)°. The C—N—NH—C torsion angle is 3.4 (3)°. The molecule possesses an intramolecular N—H⋯O hydrogen bond. In the crystal structure, adjacent molecules are linked through intermolecular C—H⋯O hydrogen bonds, forming dimers

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 ▶). graphic file with name e-65-o3272-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₃N₃O₄
M _r = 299.28
Monoclinic,
a = 11.1843 (2) Å
b = 11.3718 (3) Å
c = 13.0519 (2) Å
β = 121.792 (2)°
V = 1410.96 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.15 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.985, T _max = 0.988
8270 measured reflections
3048 independent reflections
1964 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.138
S = 1.02
3048 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.29 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/S160053680905079X/wn2369sup1.cif

e-65-o3272-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905079X/wn2369Isup2.hkl

e-65-o3272-Isup2.hkl^{(149.6KB, 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—H2A⋯O1	0.91 (1)	1.94 (2)	2.644 (2)	133 (2)
C3—H3⋯O2ⁱ	0.93	2.50	3.260 (2)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support of this work was provided by the Research Foundation of Liaoning Province (grant No. 2008470).

supplementary crystallographic information

Comment

Hydrazones derived from the condensation of aldehydes with hydrazides have been shown 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 great deal of hydrazones 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 also reported the crystal structures of a few hydrazones (Ban & Li, 2008a,b; Li & Ban, 2009a,b). In this paper, we report the crystal structure of the title compound.

In the structure of the title compound (Fig. 1) the molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the two benzene rings is 6.8 (2)°. In the 2-methoxyphenyl unit, the methoxy group is nearly coplanar with the mean plane of the C9–C14 ring; the atom C15 deviates from this plane by 0.002 (2) Å. The torsion angle C7—N1—N2—C8 is 3.4 (3)°. The molecule possesses an intramolecular N—H···O hydrogen bond (Table 1, Fig. 1).

In the crystal structure, adjacent molecules are linked through intermolecular C—H···O hydrogen bonds (Table 1), forming dimers (Fig. 2).

Experimental

The compound was prepared by refluxing 4-nitrobenzaldehyde (1.0 mol) with 2-methoxybenzohydrazide (1.0 mol) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. The colorless solid product was filtered, and washed three times with methanol. Colorless block crystals of the title compound were obtained from a methanol solution by slow evaporation in air.