4-Chloro-N′-(2-hy­droxy-4-meth­oxy­benzyl­idene)benzohydrazide methanol monosolvate

Feng Zhi; Rong Wang; Yi Zhang; Qiang Wang; Yi-Lin Yang

doi:10.1107/S1600536811039778

. 2011 Oct 5;67(Pt 11):o2825. doi: 10.1107/S1600536811039778

4-Chloro-N′-(2-hydroxy-4-methoxybenzylidene)benzohydrazide methanol monosolvate

Feng Zhi ^a, Rong Wang ^a, Yi Zhang ^a, Qiang Wang ^a, Yi-Lin Yang ^a,^*

PMCID: PMC3247565 PMID: 22219870

Abstract

The title compound, C₁₅H₁₃ClN₂O₃·CH₃OH, was synthesized by the condensation reaction of 2-hydroxy-4-methoxybenzaldehyde with 4-chlorobenzohydrazide in methanol. The Schiff base molecule displays a trans configuration with respect to the C=N and C—N bonds. The dihedral angle between the two benzene rings is 5.3 (2)°. In the crystal, molecules are linked by N—H⋯O and O—H⋯O hydrogen-bond interactions into chains running parallel to the a axis. An intramolecular O—H⋯N hydrogen bond is observed.

Related literature

For background to Schiff base compounds, see: Fan et al. (2007 ▶); Kim et al. (2005 ▶); Nimitsiriwat et al. (2004 ▶). For their biological activity, see: Chen et al. (1997 ▶); Ren et al. (2002 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Yang (2008 ▶); Zhi (2008 ▶, 2009 ▶); Zhi & Yang (2007 ▶).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₃·CH₄O
M _r = 336.77
Triclinic,
a = 6.570 (2) Å
b = 10.343 (3) Å
c = 12.707 (3) Å
α = 100.371 (2)°
β = 91.864 (2)°
γ = 101.663 (2)°
V = 829.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 298 K
0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.959, T _max = 0.971
5945 measured reflections
3022 independent reflections
1724 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.144
S = 1.01
3022 reflections
216 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811039778/rz2644sup1.cif

e-67-o2825-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039778/rz2644Isup2.hkl

e-67-o2825-Isup2.hkl^{(148.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039778/rz2644Isup3.cml

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⋯O2ⁱ	0.82	1.83	2.646 (3)	177
N2—H2⋯O4	0.90 (1)	2.00 (1)	2.876 (3)	163 (2)
O1—H1⋯N1	0.82	1.96	2.676 (3)	146

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the Third Affiliated Hospital of Suzhou University is acknowledged.

supplementary crystallographic information

Comment

In recent years, much attention has been focused on the synthesis, structures, and properties of Schiff base compounds (Fan et al., 2007; Kim et al., 2005; Nimitsiriwat et al., 2004). Some of the compounds have been found to have excellent pharmacological and antibacterial activity (Chen et al., 1997; Ren et al., 2002). We report herein the crystal structure of the title new Schiff base compound (Fig. 1) derived from the condensation reaction of 2-hydroxy-4-methoxybenzaldehyde with 4-chlorobenzohydrazide.

The asymmetric unit of the title compound contains a Schiff base molecule and a methanol molecule of crystallization. The Schiff base molecule displays a trans configuration with respect to the C═N and C–N bonds. There is an intramolecular O—H···N hydrogen bond in the molecule. The dihedral angle between the two benzene rings is 5.3 (2)°. All the bond lengths are within normal ranges and comparable to those in other similar compounds (Mohd Lair et al., 2009; Fun et al., 2008; Yang, 2008; Zhi, 2008; Zhi & Yang, 2007; Zhi, 2009). In the crystal (Fig. 2), molecules are linked by N—H···O and O—H···O hydrogen interactions into one-dimensional chains along the a axis (Table 1).

Experimental

2-Hydroxy-4-methoxybenzaldehyde (0.01 mol, 1.52 g) and 4-chlorobenzohydrazide (0.01 mol, 1.71 g) were dissolved in methanol (50 ml). The mixture was stirred at room temperature to give a clear colourless solution. Crystals of the title compound were formed by slow evaporation of the solvent for several days at room temperature.