N′-(2,3-Dimethoxy­benzyl­idene)-2-hydr­oxy-3-methyl­benzohydrazide

You-Yue Han; Qiu-Rong Zhao

doi:10.1107/S1600536810012122

. 2010 Apr 2;66(Pt 5):o1026. doi: 10.1107/S1600536810012122

N′-(2,3-Dimethoxybenzylidene)-2-hydroxy-3-methylbenzohydrazide

You-Yue Han ^a,^*, Qiu-Rong Zhao ^a

PMCID: PMC2979136 PMID: 21579090

Abstract

In the title compound, C₁₇H₁₈N₂O₄, the dihedral angle between the two benzene rings is 6.0 (2)° and the molecule adopts an E configuration with respect to the C=N bond. There is an intramolecular O—H⋯O hydrogen bond in the molecule, which generates an S(6) ring. In the crystal, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming C(4) chains running along the c axis.

Related literature

For a related structure and background information, see: Han & Zhao (2010 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₈N₂O₄
M _r = 314.33
Orthorhombic,
a = 14.923 (3) Å
b = 24.329 (5) Å
c = 8.7422 (17) Å
V = 3174.0 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.984, T _max = 0.986
17128 measured reflections
3461 independent reflections
1998 reflections with I > 2σ(I)
R _int = 0.223

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.175
S = 0.92
3461 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.30 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/S1600536810012122/hb5386sup1.cif

e-66-o1026-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012122/hb5386Isup2.hkl

e-66-o1026-Isup2.hkl^{(169.8KB, 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
O4—H4⋯O3	0.82	1.91	2.630 (2)	146
N2—H2A⋯O3ⁱ	0.90	2.17	3.030 (2)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Applied Chemistry Key Subject of Anhui Province (No. 200802187 C). The authors thank Mr Yuan-Guang Zhang of Anqing Normal University for his help with growing the crystals.

supplementary crystallographic information

Comment

As part of our ongoing studies of hydrazones (Han & Zhao, 2010), we now report the structure of the title compound, (I).

In the molecule of the title compound, Fig. 1, the dihedral angle between the two benzene rings is 6.0 (2)°. The molecule adopts an E configuration with respect to the C═N bond. There is an intramolecular O–H···O hydrogen bond (Table 1) in the molecule. All the bond lengths are within normal ranges (Allen et al., 1987).

In the crystal structure, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 1) to form chains running along the c axis (Fig. 2).

Experimental

A mixture of 2,3-dimethoxybenzaldehyde (0.166 g, 1 mmol) and 2-hydroxy-3-methylbenzohydrazide (0.166 g, 1 mmol) in 50 ml me thanol was stirred at room temperature for 1 h. The mixture was filtered to remove impurities, and then left at room temperature. After a few days, colourless blocks of (I) were formed.