2-Hydr­oxy-N′-(2-hydr­oxy-3-meth­oxy-5-nitro­benzyl­idene)-3-methyl­benzo­hydrazide

You-Yue Han; Yong-Hong Li; Qiu-Rong Zhao

doi:10.1107/S1600536810012912

. 2010 Apr 14;66(Pt 5):o1084. doi: 10.1107/S1600536810012912

2-Hydroxy-N′-(2-hydroxy-3-methoxy-5-nitrobenzylidene)-3-methylbenzohydrazide

You-Yue Han ^a,^*, Yong-Hong Li ^a, Qiu-Rong Zhao ^a

PMCID: PMC2979167 PMID: 21579138

Abstract

In the title compound, C₁₆H₁₅N₃O₆, the dihedral angle between the two benzene rings is 0.9 (2)°. The molecule adopts an E configuration with respect to the C=N bond. There are intramolecular O—H⋯N and O—H⋯O hydrogen bonds in the molecule. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds to form chains running along the c axis.

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 ▶); Cukurovali et al. (2006 ▶). For the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Lin & Sang (2009 ▶); Suleiman Gwaram et al. (2010 ▶). For the hydrazone compounds we reported recently, see: Han & Zhao (2010a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). For similar compounds, see: Li & Ban (2009 ▶); Lo & Ng (2009 ▶); Ning & Xu (2009 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C₁₆H₁₅N₃O₆
M _r = 345.31
Monoclinic,
a = 7.482 (1) Å
b = 17.158 (1) Å
c = 12.250 (1) Å
β = 91.565 (1)°
V = 1572.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.10 × 0.07 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.989, T _max = 0.994
14545 measured reflections
2612 independent reflections
2165 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.108
S = 1.07
2612 reflections
233 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.27 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/S1600536810012912/hg2671sup1.cif

e-66-o1084-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012912/hg2671Isup2.hkl

e-66-o1084-Isup2.hkl^{(128.3KB, 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
N3—H3⋯O6ⁱ	0.90 (1)	2.22 (1)	3.0190 (17)	147 (2)
O4—H4⋯O3	0.82	1.79	2.5192 (15)	148
O1—H1⋯N2	0.82	1.90	2.6166 (17)	145

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Applied Chemistry Key Subject of Anhui Province (grant No. 200802187C).

supplementary crystallographic information

Comment

Hydrazone compounds have been widely investigated for their biological properties (Patil et al., 2010; Cukurovali et al., 2006). Furthermore, the crystal structures of the hydrazone compounds have also attracted much attention in recent years (Mohd Lair et al., 2009; Lin & Sang, 2009; Suleiman Gwaram et al., 2010). As a continuous work on the structural characterization of such compounds (Han & Zhao, 2010a,b), the title new hydrazone compound is reported.

In the title compound, Fig. 1, the dihedral angle between the two benzene rings is 0.9 (2)°. The molecule adopts an E configuration with respect to the C═N bond. There are intramolecular O—H···N and O—H···O hydrogen bonds in the molecule (Table 1). All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable with those in the similar compounds (Li & Ban, 2009; Lo & Ng, 2009; Ning & Xu, 2009; Zhu et al., 2009).

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 3-methoxy-5-nitrosalicylaldehyde (0.197 g, 1 mmol) and 2-hydroxy-3-methylbenzohydrazide (0.166 g, 1 mmol) in 50 ml methanol 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, single crystals of the title compound, suitable for X-ray diffraction, were formed.