(E)-2,4-Dihydr­oxy-N′-(2-hydr­oxy-3-meth­oxy-5-nitro­benzyl­idene)benzohydrazide dihydrate

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

doi:10.1107/S1600536810013000

. 2010 Apr 14;66(Pt 5):o1085–o1086. doi: 10.1107/S1600536810013000

(E)-2,4-Dihydroxy-N′-(2-hydroxy-3-methoxy-5-nitrobenzylidene)benzohydrazide dihydrate

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

PMCID: PMC2979277 PMID: 21579139

Abstract

The asymmetric unit of the title compound, C₁₅H₁₃N₃O₇·2H₂O, consists of a hydrazone molecule and two solvent water molecules. The molecule adopts an E configuration with respect to the C=N bond. It is relatively planar, with a dihedral angle between the two benzene rings of 2.6 (1)°. There are intramolecular O—H⋯N and O—H⋯O hydrogen bonds in the hydrazone molecule. In the crystal structure, symmetry-related molecules are linked through intermolecular N—H⋯O and O—H⋯O hydrogen bonds to form a three-dimensional network.

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 have reported on recently, see: Han & Zhao (2010a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). For the crystal structures of similar compounds, see: Li & Ban (2009 ▶); Lo & Ng (2009 ▶); Ning & Xu (2009 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O₇·2H₂O
M _r = 383.32
Triclinic,
a = 7.976 (2) Å
b = 9.325 (2) Å
c = 11.547 (3) Å
α = 95.43 (2)°
β = 96.21 (2)°
γ = 102.01 (2)°
V = 829.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.13 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; Bruker, 2001 ▶) T _min = 0.971, T _max = 0.975
11747 measured reflections
4268 independent reflections
1790 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.143
S = 0.94
4268 reflections
263 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.23 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013000/su2173sup1.cif

e-66-o1085-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013000/su2173Isup2.hkl

e-66-o1085-Isup2.hkl^{(209.1KB, 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
O8—H8B⋯O4ⁱ	0.86 (2)	2.39 (2)	2.953 (2)	124 (2)
O8—H8B⋯O7ⁱ	0.86 (2)	2.18 (1)	3.001 (3)	163 (2)
O9—H9B⋯O3ⁱⁱ	0.85 (2)	2.19 (1)	3.032 (2)	170 (3)
O9—H9A⋯O2ⁱⁱⁱ	0.86 (1)	1.98 (1)	2.840 (2)	176 (2)
O8—H8A⋯O9^iv	0.86 (2)	1.93 (1)	2.786 (2)	176 (2)
N1—H1A⋯O5^v	0.88 (1)	2.55 (2)	3.183 (3)	130 (2)
N1—H1A⋯O8ⁱⁱ	0.88 (1)	2.45 (2)	3.195 (3)	143 (2)
O4—H4⋯N2	0.82	1.85	2.569 (2)	146
O2—H2⋯O3	0.82	1.80	2.526 (2)	147
O1—H1⋯O8^vi	0.82	1.91	2.718 (2)	169

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

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 continuation of our work on the structural characterization of such compounds (Han & Zhao, 2010a,b), we report herein on the synthesis and crystal structure of the new title hydrazone compound.

The title compound, Fig. 1, consists of a hydrazone molecule and two water molecules of crystallization. The hydrazone molecule adopts an E configuration with respect to the C═N bond. The dihedral angle between the two benzene rings in the hydrazone molecule is 2.6 (1)°. There are intramolecular O—H···N and O—H···O hydrogen bonds in the hydrazone molecule (Fig. 1 and Table 1). All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable with those in similar compounds (Li & Ban, 2009; Lo & Ng, 2009; Ning & Xu, 2009; Zhu et al., 2009).

In the crystal structure of the title compound symmetry related molecules are linked through intermolecular N—H···O and O—H···O hydrogen bonds to form a three-dimensional network (Table 1 and Fig. 2).

Experimental

A mixture of 3-methoxy-5-nitrosalicylaldehyde (0.197 g, 1 mmol) and 2,4-dihydroxybenzohydrazide (0.168 g, 1 mmol) in 50 ml methanol was stirred at room temperature for 1 h. The mixture was then filtered to remove any impurities, and the filtrate left at room temperature for slow evaporation of the solvent. After a few days colourless block-like crystals of the title compound, suitable for X-ray diffraction, were formed.