N′-(2-Hydr­oxy-4-methoxy­benzyl­idene)-4-methoxy­benzohydrazide

Xinyou Zhang

doi:10.1107/S1600536809032449

. 2009 Aug 22;65(Pt 9):o2200. doi: 10.1107/S1600536809032449

N′-(2-Hydroxy-4-methoxybenzylidene)-4-methoxybenzohydrazide

Xinyou Zhang ^a,^*

PMCID: PMC2970121 PMID: 21577603

Abstract

In the title compound, C₁₆H₁₆N₂O₄, the dihedral angle between the two benzene rings is 8.7 (2)°. The molecule adopts an E configuration about the C=N bond, with an intramolecular O—H⋯N hydrogen bond involving the hydroxy substituent and the hydrazide N atom. In the crystal structure, adjacent molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains propagating in the b-axis direction.

Related literature

For related structures, see: Alhadi et al. (2008 ▶); Küçükgüzel et al. (2003 ▶); Mohd Lair et al. (2009a ▶,b ▶); Li et al. (2009 ▶); Zhang et al. (2009 ▶). For a similar hydrazone compound, see: Zhang (2009 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₄
M _r = 300.31
Monoclinic,
a = 17.692 (2) Å
b = 5.4131 (7) Å
c = 14.933 (2) Å
β = 97.431 (7)°
V = 1418.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.977, T _max = 0.980
8164 measured reflections
3069 independent reflections
2001 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.129
S = 1.03
3069 reflections
205 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032449/su2137sup1.cif

e-65-o2200-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032449/su2137Isup2.hkl

e-65-o2200-Isup2.hkl^{(150.6KB, 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
O1—H1⋯N1	0.82	1.86	2.577 (2)	146
N2—H2⋯O2ⁱ	0.90 (1)	2.393 (11)	3.281 (2)	168 (2)

Open in a new tab

Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Hydrazone compounds are readily synthesized by the reaction of aldehydes with hydrazides. A large number of hydrazone compounds have been reported (Alhadi et al., 2008; Küçükgüzel et al., 2003; Li et al., 2009; Zhang et al., 2009). Recently, the author reported on the crystal structure of a hydrazone compound derived from the reaction of 2-methoxybenzaldehyde with 4-methoxybenzohydrazide (Zhang, 2009). Herein, the crystal structure of the new title hydrazone, prepared from the reaction of 2-hydroxy-4-methoxybenzaldehyde with 4-methoxybenzohydrazide, is reported on.

The molecule structure of the title compound is illustrated in Fig. 1. The molecule adopts an E configuration about the C═N bond. The dihedral angle involving the two benzene rings is 8.7 (2)°. There is an intramolecular O1—H1···N1 hydrogen bond, involving the hydroxyl substituent and the hydrazide N-atom (Table 1). All the bond lengths are within normal values (Allen et al., 1987) and are comparable with those observed in similar compounds (Mohd Lair et al., 2009a,b; Zhang, 2009).

In the crystal structure of the title compound adjacent molecules are linked through intermolecular N—H···O hydrogen bonds, forming chains propagating in b direction (Table 1 and Fig. 2).

Experimental

2-Hydroxy-4-methoxybenzaldehyde (1.0 mmol, 152.2 mg) and 4-methoxybenzohydrazide (1.0 mmol, 166.2 mg) were mixed in a methanol solution, and the mixture was refluxed for 1 h. Colorless block-shaped crystals of the title compound were formed by slow evaporation of the solution in air.