N′-(5-Chloro-2-hy­droxy­benzyl­idene)-4-meth­oxy­benzohydrazide

Yao Tan

doi:10.1107/S1600536812010707

. 2012 Mar 17;68(Pt 4):o1079. doi: 10.1107/S1600536812010707

N′-(5-Chloro-2-hydroxybenzylidene)-4-methoxybenzohydrazide

Yao Tan ^a,^*

PMCID: PMC3344034 PMID: 22589943

Abstract

The asymmetric unit of the title compound, C₁₅H₁₃ClN₂O₃, contains two independent hydrazone molecules. Each molecule adopts an E configuration with respect to the methylidene unit and forms an intramolecular O—H⋯N hydrogen bond. The principal difference between the two unique molecules is the relative orientation of the two benzene rings, the dihedral angles between them being 4.0 (3) and 65.9 (3)°, respectively. In the crystal, molecules are linked through N—H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For similar hydrazone derivatives, see: Li (2012 ▶); Zhu et al. (2012 ▶); Shen et al. (2012 ▶); Liu et al. (2011 ▶); Lei (2011 ▶).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₃
M _r = 304.72
Monoclinic,
a = 17.569 (3) Å
b = 8.367 (2) Å
c = 19.454 (3) Å
β = 93.683 (3)°
V = 2853.8 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 K
0.11 × 0.08 × 0.07 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.970, T _max = 0.981
11127 measured reflections
3752 independent reflections
2545 reflections with I > 2σ(I)
R _int = 0.031
θ_max = 22.7°

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.105
S = 1.02
3752 reflections
389 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536812010707/sj5210sup1.cif

e-68-o1079-sup1.cif^{(29.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010707/sj5210Isup2.hkl

e-68-o1079-Isup2.hkl^{(184KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010707/sj5210Isup3.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
N4—H4B⋯O2ⁱ	0.89 (1)	1.98 (1)	2.843 (3)	164 (2)
N2—H2⋯O5	0.89 (1)	2.01 (1)	2.883 (3)	166 (2)
O4—H4⋯N3	0.82	1.82	2.540 (3)	145
O1—H1⋯N1	0.82	1.80	2.526 (3)	146

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

As an extension of the work on the structures of hydrazone derivatives (Li, 2012; Zhu et al., 2012; Shen et al., 2012; Liu et al., 2011; Lei, 2011), the author reports here the structure of a new benzohydrazide compound, (I). The asymmetric unit of (I) contains two independent hydrazone molecules, Fig 1. Each molecule adopts a trans configuration with respect to the methylidene unit. The dihedral angles between the C1—C6 and C9—C14 benzene rings is 4.0 (3)°. The dihedral angles between the C16—C21 and C24—C29 benzene rings is 65.9 (3)°. In the crystal, molecules are linked through N—H···O hydrogen bonds (Table 1), to form chains running along the c-axis (Fig. 2).

Experimental

4-Methoxybenzohydrazide (0.1 mmol, 16.6 mg) and 5-chloro-2-hydroxybenzaldehyde (0.1 mmol, 15.6 mg) were dissolved in methanol (30 ml). The reaction mixture was heated under reflux for 30 min and cooled gradually to room temperature. Thin, colourless needle-like crystals were obtained by slow evaporation of the solution containing the compound in air.