4-Meth­oxy-N′-(3-nitro­benzyl­idene)benzohydrazide

Jin-Long Hou; Ye Bi

doi:10.1107/S1600536812020454

. 2012 May 16;68(Pt 6):o1725. doi: 10.1107/S1600536812020454

4-Methoxy-N′-(3-nitrobenzylidene)benzohydrazide

Jin-Long Hou ^a,^*, Ye Bi ^a

PMCID: PMC3379315 PMID: 22719513

Abstract

In the title compound, C₁₅H₁₃N₃O₄, the dihedral angle between the benzene rings is 3.1 (3)°. The molecule displays an E conformation about the C=N bond. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, generating chains that propagate along the b-axis direction. There is also a C—H⋯O interaction present.

Related literature

For the biological properties of hydrazone compounds, see: Cukurovali et al. (2006 ▶); Karthikeyan et al. (2006 ▶); Kucukguzel et al. (2006 ▶). For related hydrazone compounds, see: Hou (2009 ▶, 2012 ▶); Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Zhang et al. (2009 ▶); Khaledi et al. (2008 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). graphic file with name e-68-o1725-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₃N₃O₄
M _r = 299.28
Monoclinic,
a = 6.8472 (17) Å
b = 4.8269 (16) Å
c = 21.414 (3) Å
β = 96.696 (2)°
V = 702.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.17 × 0.13 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.982, T _max = 0.987
3686 measured reflections
1445 independent reflections
1275 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.085
S = 1.05
1445 reflections
203 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.16 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 datablock(s) global, I. DOI: 10.1107/S1600536812020454/su2422sup1.cif

e-68-o1725-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020454/su2422Isup2.hkl

e-68-o1725-Isup2.hkl^{(71.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812020454/su2422Isup3.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
N3—H3⋯O3ⁱ	0.90 (2)	2.03 (2)	2.861 (3)	154 (3)
C6—H6⋯O1ⁱⁱ	0.93	2.60	3.268 (3)	129

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

Acknowledgments

This project was supported by the Research Foundation of the Education Bureau of Heilongjiang Province, China (grant No. 11521312).

supplementary crystallographic information

Comment

Hydrazones derived from the condensation reactions of hydrazides with aldehydes show excellent biological properties (Cukurovali et al., 2006; Karthikeyan et al., 2006; Kucukguzel et al., 2006). In the last few years, the crystal structure of a large number of hydrazone compounds have been reported (Hou, 2009; Hou, 2012; Lair et al., 2009; Fun et al., 2008; Zhang et al., 2009; Khaledi et al., 2008). Herein we report on the synthesis and crystal structure of the title compound, derived from the condensation reaction of 3-nitrobenzaldehyde and 4-methoxybenzohydrazide.

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the two benzene rings is 3.1 (3)°. The molecule displays an E conformation about the C═N bond. All the bond lengths are within normal ranges (Allen et al., 1987).

In the crystal, molecules are linked via N–H···O hydrogen bonds (Table 1) generating chains along the b axis direction (Fig. 2). There is also a C-H···O interaction present (Table 1).

Experimental

3-Nitrobenzaldehyde (1.0 mmol, 151 mg) and 4-methoxybenzohydrazide (1.0 mmol, 166 mg) were mixed and refluxed with stirring for two hours. Yellow single crystals were formed after slow evaporation of the solution in air for a week.