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

Guo-Biao Cao

doi:10.1107/S1600536809039713

. 2009 Oct 3;65(Pt 11):o2645. doi: 10.1107/S1600536809039713

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

Guo-Biao Cao ^a,^*

PMCID: PMC2971394 PMID: 21578259

Abstract

The molecule of the title compound, C₁₆H₁₆N₂O₃, displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 99.0 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For examples of the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Li & Ban (2009 ▶); Zhu et al. (2009 ▶); Yang (2007 ▶); You et al. (2008 ▶). For the hydrazone compounds we have reported previously, see: Qu et al. (2008 ▶); Yang et al. (2008 ▶); Cao & Lu (2009a ▶,b ▶); Qu & Cao (2009 ▶); Cao & Wang (2009 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₃
M _r = 284.31
Orthorhombic,
a = 14.990 (1) Å
b = 8.076 (1) Å
c = 24.122 (2) Å
V = 2920.2 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.985, T _max = 0.987
16039 measured reflections
3011 independent reflections
1225 reflections with I > 2σ(I)
R _int = 0.117

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.149
S = 0.92
3011 reflections
196 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809039713/rz2367sup1.cif

e-65-o2645-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039713/rz2367Isup2.hkl

e-65-o2645-Isup2.hkl^{(147.9KB, 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⋯O2ⁱ	0.899 (10)	2.093 (15)	2.940 (3)	157 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The vital foundation of Ankang University (project No. 2008AKXY012), and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 02JK202) are gratefully acknowledged.

supplementary crystallographic information

Comment

Study on the crystal structures of hydrazone derivatives is an interesting topic in structural chemistry. Recently, the crystal structures of a number of hydrazone compounds have been reported (Mohd Lair et al., 2009; Fun et al., 2008; Li & Ban, 2009; Zhu et al., 2009; Yang, 2007; You et al., 2008). As a continuation of our work in this area (Qu et al., 2008; Yang et al., 2008; Cao & Lu, 2009a,b; Qu & Cao, 2009; Cao & Wang, 2009), the title new hydrazone compound, derived from the reaction of 4-methoxybenzaldehyde with an equimolar quantity of 2-methoxybenzohydrazide, is reported.

The molecule of the title compound (Fig. 1) displays an E configuration about the C═N bond. The dihedral angle between the two benzene rings is 99.0 (2)°. In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form chains running along the b axis (Fig. 2).

Experimental

The title compound was prepared by refluxing 4-methoxybenzaldehyde (0.1 mmol, 13.6 mg) with 2-methoxybenzohydrazide (0.1 mmol, 16.6 mg) in methanol (20 ml). Colourless block-like crystals were formed by slow evaporation of the solution in air.