N′-(2,4-Dichloro­benzyl­idene)-4-methoxy­benzohydrazide methanol solvate

Min Liang; Dong-Hui Zou

doi:10.1107/S1600536809022624

. 2009 Jun 17;65(Pt 7):o1609. doi: 10.1107/S1600536809022624

N′-(2,4-Dichlorobenzylidene)-4-methoxybenzohydrazide methanol solvate

Min Liang ^a,^*, Dong-Hui Zou ^b

PMCID: PMC2969251 PMID: 21582882

Abstract

In the title compound, C₁₅H₁₂Cl₂N₂O₂·CH₃OH, the hydrazone molecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 4.6 (2)°. In the crystal structure, the hydrazone and methanol molecules are linked into a chain propagating along the a axis via N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the biological properties of hydrazone compounds, see: Küçükgüzel et al. (2003 ▶); Charkoudian et al. (2007 ▶). For the crystal structures of hydrazone compounds, see: Fun et al. (2008 ▶); Lo & Ng (2009 ▶); Ren (2009 ▶); Zhang (2009 ▶). For related structures, see: Wu (2009 ▶); Peng & Hou (2008 ▶); Mohd Lair et al. (2009 ▶).

Experimental

Crystal data

C₁₅H₁₂Cl₂N₂O₂·CH₄O
M _r = 355.21
Triclinic,
a = 6.7401 (11) Å
b = 8.9583 (14) Å
c = 14.567 (2) Å
α = 75.085 (2)°
β = 81.570 (2)°
γ = 83.445 (2)°
V = 838.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.924, T _max = 0.931
4896 measured reflections
3557 independent reflections
2461 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.128
S = 1.03
3557 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536809022624/ci2826sup1.cif

e-65-o1609-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022624/ci2826Isup2.hkl

e-65-o1609-Isup2.hkl^{(174.4KB, 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⋯O3ⁱ	0.893 (10)	2.013 (12)	2.889 (3)	167 (3)
O3—H3⋯O1ⁱⁱ	0.82	1.99	2.780 (2)	163

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

Acknowledgments

The authors acknowledge Qiqihar University for funding this study.

supplementary crystallographic information

Comment

Hydrazones possess excellent antibacterial, antifungal, and antitumor activities (Küçükgüzel et al., 2003; Charkoudian et al., 2007). Recently, the crystal structures of some hydrazone compounds have been reported (Fun et al., 2008; Lo & Ng, 2009; Ren, 2009; Zhang, 2009). We report herein the crystal structure of the title new hydrazone compound.

The asymmetric unit of the title compound contains a hydrazone molecule and a methanol molecule. In the hydrazone molecule, the dihedral angle between the two benzene rings is 4.6 (2)°. The hydrazone molecule exists in an E configuration with respect to the methylidene group. All the bond lengths are normal and comparable to those in similar hydrazone compounds (Wu, 2009; Peng & Hou, 2008; Mohd Lair et al., 2009).

In the crystal structure of the title compound, the hydrazone molecules are linked by the methanol molecules through N—H···O and O—H···O hydrogen bonds (Table 1), forming chains propagating along the a axis (Fig. 2).

Experimental

Equimolar quantities (1.0 mmol each) of 2,4-dichlorobenzaldehyde and 4-methoxybenzohydrazide were mixed and refluxed in methanol. The reaction mixture was cooled to room temperature to give a clear colourless solution. Colourless single crystals of the title compound were formed by slow evaporation of the solution in air.