N′-(3,5-Dichloro-2-hydroxy­benzyl­idene)-3-methoxy­benzohydrazide methanol solvate

Chun-Hua Ling; Yan-Bin Chen; Jian-An Huang; Cheng Ji; Peng Liu

doi:10.1107/S160053680801235X

. 2008 Apr 30;64(Pt 5):o948. doi: 10.1107/S160053680801235X

N′-(3,5-Dichloro-2-hydroxybenzylidene)-3-methoxybenzohydrazide methanol solvate

Chun-Hua Ling ^a, Yan-Bin Chen ^a, Jian-An Huang ^a, Cheng Ji ^a,^*, Peng Liu ^b

PMCID: PMC2961072 PMID: 21202428

Abstract

In the title compound, C₁₅H₁₂Cl₂N₂O₃·CH₃OH, the Schiff base molecule is nearly planar, with a dihedral angle of 4.5 (2)° between the two benzene rings. An intramolecular O—H⋯N hydrogen bond is observed. The methanol solvent molecule is linked to the Schiff base molecule through intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the synthesis of Schiff base compounds, see: Herrick et al. (2008 ▶); Suresh et al. (2007 ▶); Liu et al. (2007 ▶). For the background on biological activities, see: Bhandari et al. (2008 ▶); Sinha et al. (2008 ▶); Sun et al. (2008 ▶). For related structures, see: Wang et al. (2008 ▶); Tang (2008a ▶,b ▶); Yang & Zheng (2007 ▶).

Experimental

Crystal data

C₁₅H₁₂Cl₂N₂O₃·CH₄O
M _r = 371.21
Triclinic,
a = 7.742 (3) Å
b = 9.070 (3) Å
c = 12.296 (4) Å
α = 92.422 (5)°
β = 98.948 (5)°
γ = 96.954 (5)°
V = 845.0 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 298 (2) K
0.27 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.898, T _max = 0.923
6888 measured reflections
3452 independent reflections
2253 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.131
S = 1.04
3452 reflections
224 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.24 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801235X/ci2593sup1.cif

e-64-0o948-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801235X/ci2593Isup2.hkl

e-64-0o948-Isup2.hkl^{(169.3KB, 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
N2—H2⋯O4ⁱ	0.899 (10)	1.997 (12)	2.881 (3)	167 (3)
O4—H4⋯O2	0.82	2.35	2.989 (3)	135
O4—H4⋯O2ⁱⁱ	0.82	2.34	3.023 (3)	141
O1—H1⋯N1	0.82	1.84	2.557 (3)	145

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Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

Schiff base compounds can be easily synthesized from the reaction of aldehydes with primary amines (Herrick et al., 2008; Suresh et al., 2007; Liu et al., 2007). These compounds show interesting biological activities, especially antimicrobial activities (Bhandari et al., 2008; Sinha et al., 2008; Sun et al., 2008). Recently, the crystal structures of a few Schiff base compounds obtained from the derivatives of salicylaldehyde with benzohydrazide have been reported (Wang et al., 2008; Tang, 2008a,b; Yang & Zheng, 2007). We report here the crystal structure of a new Schiff base compound, derived from 3,5-dichlorosalicylaldehyde and 3-methoxybenzohydrazide.

The asymmetric unit consists of a Schiff base molecule and a methanol molecule of crystallization (Fig. 1). The Schiff base molecule is nearly planar, with a maximum deviation of 0.133 (1) Å for atom Cl1. The dihedral angle between the two benzene rings is 4.5 (2)°. An intramolecular O—H···N hydrogen bond is observed in the Schiff base molecule. The methanol molecule of crystallization is linked to the Schiff base molecule through intermolecular N—H···O and O—H···O hydrogen bonds (Table 1 and Fig.2).

Experimental

3,5-Dichlorosalicylaldehyde (0.1 mmol, 19.0 mg) and 3-methoxybenzohydrazide (0.1 mmol, 16.6 mg) were dissolved in methanol (20 ml). The mixture was stirred at room temperature to give a clear yellow solution. Yellow block-shaped crystals were formed after a week.