N′-(2-Hydroxy­benzyl­idene)-2-methoxy­benzohydrazide monohydrate

Jiu-Fu Lu; Suo-Tian Min; Xiao-Hui Ji; Zhong-Hai Dang

doi:10.1107/S1600536808024483

. 2008 Aug 6;64(Pt 9):o1693. doi: 10.1107/S1600536808024483

N′-(2-Hydroxybenzylidene)-2-methoxybenzohydrazide monohydrate

Jiu-Fu Lu ^a,^*, Suo-Tian Min ^a, Xiao-Hui Ji ^a, Zhong-Hai Dang ^a

PMCID: PMC2960617 PMID: 21201682

Abstract

In the title compound, C₁₅H₁₄N₂O₃·H₂O, the Schiff base molecule is approximately planar, with a dihedral angle between the two aromatic rings of 10.2 (3)°. The molecular structure is stabilized by O—H⋯N and N—H⋯O hydrogen bonds. In the crystal structure, the Schiff base and water molecules are linked together by intermolecular O—H⋯O hydrogen bonds, forming chains parallel to the a axis.

Related literature

For general background on Schiff bases derived from condensation of aldehydes with benzohydrazides, see: Fun et al. (2008 ▶); Alhadi et al. (2008 ▶); Ali et al. (2007 ▶); Zou et al. (2004 ▶); Shan et al. (2008 ▶); Bedia et al. (2006 ▶); Terzioglu & Gürsoy (2003 ▶). For related structures, see: Nie (2008 ▶); He (2008 ▶); Shi et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₃·H₂O
M _r = 288.30
Orthorhombic,
a = 4.761 (2) Å
b = 14.035 (3) Å
c = 21.073 (4) Å
V = 1408.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.17 × 0.16 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.983, T _max = 0.985
11662 measured reflections
1808 independent reflections
1345 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.130
S = 1.06
1808 reflections
201 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536808024483/ci2646sup1.cif

e-64-o1693-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024483/ci2646Isup2.hkl

e-64-o1693-Isup2.hkl^{(89KB, 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	1.97	2.669 (3)	143
N2—H2⋯O3	0.90 (1)	1.97 (3)	2.629 (3)	129 (3)
O4—H4B⋯O2	0.88 (3)	2.01 (3)	2.880 (4)	171 (3)
O4—H4A⋯O2ⁱ	0.88 (3)	2.04 (2)	2.893 (4)	165 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge Shaanxi University of Technology for the research fund.

supplementary crystallographic information

Comment

Schiff bases derived from the condensation of aldehydes with benzohydrazides have been widely investigated, either for their structures (Fun et al., 2008; Alhadi et al., 2008; Ali et al., 2007; Zou et al., 2004; Shan et al., 2008) or for their biological properties (Bedia et al., 2006; Terzioglu & Gürsoy, 2003). This study extends the structural study on such compounds. We report here the crystal structure of the title new Schiff base compound.

The asymmetric unit of the title compound consists of a Schiff base molecule and a water molecule of crystallization (Fig. 1). The bond lengths are within normal values (Allen et al., 1987), and are comparable to the values observed in similar compounds (Nie, 2008; He, 2008; Shi et al., 2007). The dihedral angle between the two aromatic rings in the Schiff base molecule is 10.2 (3)°, indicating that the molecule is approximately coplanar. The molecular structure is stabilized by O—H···N and N—H···O hydrogen bonds.

In the crystal structure (Fig. 2), the Schiff base and water molecules are linked into chains running parallel to the a axis by intermolecular O—H···O hydrogen bonds (Table 1).

Experimental

The title compound was prepared by the Schiff base condensation of salicylaldehyde (0.1 mol) and 2-methoxybenzohydrazide (0.1 mmol) in ethanol (50 ml). The excess ethanol was removed by distillation. The colourless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were grown by slow evaporation from an ethanol solution at room temperature.