N′-(4-Chloro­benzyl­idene)-2-hydroxy­benzohydrazide

Shu-Ping Zhang; Rui Qiao; Si-Chang Shao

doi:10.1107/S160053680803972X

. 2008 Dec 10;65(Pt 1):o84. doi: 10.1107/S160053680803972X

N′-(4-Chlorobenzylidene)-2-hydroxybenzohydrazide

Shu-Ping Zhang ^a, Rui Qiao ^a, Si-Chang Shao ^a,^*

PMCID: PMC2967992 PMID: 21581722

Abstract

The title molecule, C₁₄H₁₁ClN₂O₂, adopts a trans configuration with respect to the C=N double bond. An intramolecular N—H⋯O hydrogen bond contributes to molecular conformation and the two benzene rings form a dihedral angle of 17.9 (8)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into chains running along [10 Inline graphic ].

Related literature

For general background to hydrazones and Schiff bases and their potential pharmacological and antitumor properties, see: Karthikeyan et al. (2006 ▶); Khattab (2005 ▶); Kucukguzel et al. (2006 ▶); Okabe et al. (1993 ▶).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₂
M _r = 274.70
Monoclinic,
a = 4.8557 (6) Å
b = 24.588 (3) Å
c = 11.0903 (13) Å
β = 99.710 (2)°
V = 1305.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 (2) K
0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.972, T _max = 0.977
11227 measured reflections
3126 independent reflections
2402 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.169
S = 1.12
3126 reflections
180 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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/S160053680803972X/cv2476sup1.cif

e-65-00o84-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803972X/cv2476Isup2.hkl

e-65-00o84-Isup2.hkl^{(153.4KB, 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
N1—H2⋯O1	0.80 (3)	2.01 (3)	2.624 (2)	134 (2)
O1—H1⋯O2ⁱ	0.782 (18)	1.90 (2)	2.647 (2)	159 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Natural Science Foundation of Anhui Provincial University College (grant No. 2005 KJ137).

supplementary crystallographic information

Comment

Hydrazones and Schiff bases have attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab, 2005; Karthikeyan et al., 2006; Okabe et al., 1993). We are interested in this fields. As a part of ongoing study, we report herein the crystal structure of the title compound, (I).

The molecular structure of (I) (Fig. 1) displays a trans configuration about the C=N bond. Intramolecular N—H···O hydrogen bond (Table 1) contributes to molecular conformation - the dihedral angle between the two benzene rings is 17.9 (8)°. In the crystal, the molecules are linked into chains by intermolecular O—H···O hydrongen bonds (Table 1).

Experimental

Equivalent amounts of 2-Hydroxybenzohydrazide and 3-chlorobenzohydrazide were reacted in ethanol (10 mL) for 1 h. After allowing the resulting solution to stand in air for 10 d colourless block-shaped crystals were formed on slow evaporation of the solvent.