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

Xiao-Yan Li

doi:10.1107/S160053681102366X

. 2011 Jun 25;67(Pt 7):o1798. doi: 10.1107/S160053681102366X

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

Xiao-Yan Li ^a,^*

PMCID: PMC3151996 PMID: 21837171

Abstract

In the title compound, C₁₅H₁₂Cl₂N₂O₃, the dihedral angle between the two substituted aromatic rings is 5.4 (4)°. Intramolecular O—H⋯N and N—H⋯O hydrogen bonds affect the planarity of the molcular conformation, with a mean deviation from the plane defined by the non-H atoms of 0.062 (2) Å. The molecule exists in a trans configuration with respect to the methylidene unit. In the crystal, molecules are linked by N—H⋯O interactions.

Related literature

For the crystal structures of hydrazone compounds, see: Li (2011 ▶); Hashemian et al. (2011 ▶); Lei (2011 ▶); Shalash et al. (2010 ▶).

Experimental

Crystal data

C₁₅H₁₂Cl₂N₂O₃
M _r = 339.17
Monoclinic,
a = 10.845 (7) Å
b = 12.771 (8) Å
c = 10.856 (7) Å
β = 96.683 (7)°
V = 1493.4 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 298 K
0.18 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.924, T _max = 0.928
4586 measured reflections
2978 independent reflections
2011 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.133
S = 1.02
2978 reflections
204 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ▶), 1272 Friedel pairs
Flack parameter: 0.10 (10)

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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102366X/om2438sup1.cif

e-67-o1798-sup1.cif^{(15.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102366X/om2438Isup2.hkl

e-67-o1798-Isup2.hkl^{(146.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681102366X/om2438Isup3.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
O1—H1⋯N1	0.82	1.82	2.543 (4)	146
N2—H2⋯O3	0.90 (1)	2.02 (5)	2.624 (4)	123 (5)
N2—H2⋯O1ⁱ	0.90 (1)	2.63 (4)	3.271 (5)	129 (5)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges the Zibo Vocational Institute for supporting the work.

supplementary crystallographic information

Comment

In the last few years, hydrazones have been attracted much attention for their crystal structures (Li, 2011; Hashemian et al., 2011; Lei, 2011; Shalash et al., 2010).

In the crystal structure of the title hydrazone molecule, as shown in Fig. 1, the dihedral angle between the two substituted aromatic rings is 5.4 (4)°. The intramolecular O—H···N and N—H···O hydrogen bonds (Table 1) affect the planarity of the conformation of the molecule. The molecule exists in a trans configuration with respect to the methylidene unit.

Experimental

A mixture of 2-methoxybenzhydrazide (0.166 g, 1 mmol) and 3,5-dichlorosalicylaldehyde (0.190 g, 1 mmol) in 30 ml of ethanol containing a few drops of acetic acid was refluxed for about 1 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from methanol. Colorless crystals suitable for X-ray diffraction were obtained by slow evaporation of the solution.