(E)-4-Chloro-N′-[1-(4-hydroxy­phenyl)­ethylidene]benzohydrazide

De-Suo Yang

doi:10.1107/S1600536808027001

. 2008 Aug 30;64(Pt 9):o1850. doi: 10.1107/S1600536808027001

(E)-4-Chloro-N′-[1-(4-hydroxyphenyl)ethylidene]benzohydrazide

De-Suo Yang ^a,^*

PMCID: PMC2960571 PMID: 21201821

Abstract

The molecule of the title compound, C₁₅H₁₃ClN₂O₂, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two benzene rings is 15.1 (3)°. A strong intramolecular O—H⋯N hydrogen bond is observed. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains running along [101].

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Yang (2007 ▶, 2008a ▶,b ▶). For general background, see: Bernardo et al. (1996 ▶); Musie et al. (2001 ▶); Paul et al. (2002 ▶).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₂
M _r = 288.72
Monoclinic,
a = 7.241 (3) Å
b = 23.653 (4) Å
c = 8.744 (3) Å
β = 113.682 (3)°
V = 1371.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 (2) K
0.32 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.915, T _max = 0.925
11286 measured reflections
2961 independent reflections
1543 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.143
S = 0.99
2961 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 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/S1600536808027001/ci2658sup1.cif

e-64-o1850-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027001/ci2658Isup2.hkl

e-64-o1850-Isup2.hkl^{(145.3KB, 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
O2—H2⋯N2	0.82	1.80	2.513 (3)	145
N1—H1⋯O1ⁱ	0.90 (1)	2.074 (11)	2.968 (3)	176 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges Key Laboratory Construction Support from the Education Office of Shanxi Province (project No. 05JS43).

supplementary crystallographic information

Comment

Schiff base compounds have been of great interest for a long time. These compounds play an important role in the development of coordination chemistry (Musie et al., 2001; Bernardo et al., 1996; Paul et al., 2002). Recently, we have reported a few Schiff base compounds (Yang, 2007, 2008a,b). As a further investigation of this work, the crystal structure of the title compound is reported here.

The molecule of the title compound displays a trans configuration with respect to the C?N double bond (Fig. 1). The dihedral angle between the two benzene rings is 15.1 (3)°. All the bond lengths are within normal ranges (Allen et al., 1987). The C8═N2 bond length of 1.287 (3) Å conforms to the value for a double bond. The N1—C7 bond length of 1.355 (3) Å is intermediate between a C—N single bond and a C?N double bond, because of conjugation effects in the molecule. There is a strong intramolecular hydrogen bond between the hydroxyl hydrogen and N2.

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains running along the [1 0 1] direction (Fig. 2).

Experimental

1-(2-Hydroxyphenyl)ethanone (0.1 mmol, 13.6 mg) and 4-chlorobenzohydrazide (0.1 mmol, 17.0 mg) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature to give a clear colourless solution. Single crystals of the title compound were obtained by gradual evaporation of the solvent over a period of 12 d at room temperature.