(E)-4-Chloro-N′-(4-hydroxy­benzyl­idene)­benzohydrazide

De-Suo Yang

doi:10.1107/S1600536808027013

. 2008 Aug 30;64(Pt 9):o1849. doi: 10.1107/S1600536808027013

(E)-4-Chloro-N′-(4-hydroxybenzylidene)benzohydrazide

De-Suo Yang ^a,^*

PMCID: PMC2960690 PMID: 21201820

Abstract

The molecule of the title compound, C₁₄H₁₁ClN₂O₂, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two benzene rings is 12.8 (3)°. In the crystal structure, molecules are linked through intermolecular O—H⋯O and N—H⋯O hydrogen bonds and C—H⋯π interactions, forming a three-dimensional network.

Related literature

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

Experimental

Crystal data

C₁₄H₁₁ClN₂O₂
M _r = 274.70
Orthorhombic,
a = 26.251 (3) Å
b = 12.376 (3) Å
c = 7.786 (2) Å
V = 2529.5 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 298 (2) K
0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.963, T _max = 0.971
11323 measured reflections
2164 independent reflections
1462 reflections with I > 2σ(I)
R _int = 0.078

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.116
S = 1.02
2164 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.35 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/S1600536808027013/ci2657sup1.cif

e-64-o1849-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027013/ci2657Isup2.hkl

e-64-o1849-Isup2.hkl^{(106.5KB, 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—H2A⋯O2ⁱ	0.90 (1)	2.078 (11)	2.970 (3)	171 (3)
O1—H1⋯O2ⁱⁱ	0.82	1.91	2.725 (3)	170
C6—H6⋯Cg1ⁱⁱⁱ	0.93	2.88	3.726 (3)	152

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the C1–C6 ring centroid.

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 12.8 (3)°. All the bonds are within normal ranges (Allen et al., 1987). The C7?N1 bond length of 1.268 (3) Å conforms to the value for a double bond. The bond length of 1.339 (3) Å between atoms C8 and N2 is intermediate between a C—N single bond and a C?N double bond, because of conjugation effects in the molecule.

In the crystal structure, molecules are linked through intermolecular O—H···O and N—H···O hydrogen bonds, and C—H···π interactions (Table 1), forming a three-dimensional network (Fig. 2).

Experimental

4-Hydroxybenzaldehyde (0.1 mmol, 12.2 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. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of 5 days at room temperature.