N′-(2-Chloro­benzyl­idene)benzo­hydrazide

Chuan-Gang Fan; Ming-Zhi Song

doi:10.1107/S1600536809040331

. 2009 Oct 10;65(Pt 11):o2679. doi: 10.1107/S1600536809040331

N′-(2-Chlorobenzylidene)benzohydrazide

Chuan-Gang Fan ^a,^*, Ming-Zhi Song ^a

PMCID: PMC2971129 PMID: 21578286

Abstract

The asymmetric unit of the title compound, C₁₄H₁₁ClN₂O, contains two independent molecules. In one molecule, the two aromatic rings form a dihedral angle of 45.94 (16)°, while in the second molecule this angle is 58.48 (16)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into two crystallographically independent sets of chains propagating along [001].

Related literature

For the biological properties of Schiff base ligands, see: Bedia et al. (2006 ▶). For related crystal structures, see: Fun et al. (2008 ▶); Alhadi et al. (2008 ▶); Nie (2008 ▶).

Experimental

Crystal data

C₁₄H₁₁ClN₂O
M _r = 258.70
Tetragonal,
a = 13.5588 (17) Å
c = 14.3993 (18) Å
V = 2647.2 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 K
0.45 × 0.42 × 0.38 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.885, T _max = 0.902
10838 measured reflections
4614 independent reflections
2766 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.093
S = 1.03
4614 reflections
325 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ▶), 2105 Friedel pairs
Flack parameter: −0.03 (7)

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 I, global. DOI: 10.1107/S1600536809040331/cv2620sup1.cif

e-65-o2679-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040331/cv2620Isup2.hkl

e-65-o2679-Isup2.hkl^{(226KB, 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—H1⋯O1ⁱ	0.86	2.01	2.854 (4)	168
N3—H3⋯O2ⁱⁱ	0.86	2.09	2.928 (4)	166

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge the financial support of the Foundation of Binzhou University (grant No. BZXYLG200609).

supplementary crystallographic information

Comment

Schiff base ligands have received considerable attention during the last decades, mainly because of diversity of their structures and biological properties (Bedia et al., 2006). We report here the crystal structure of the title new Schiff base compound (I).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable with those observed in similar compounds (Nie et al., 2008; Fun et al., 2008; Alhadi et al., 2008). The asymmetric unit of (I) contains two independent molecules- A and B, respectively. In molecule A, two aromatic rings form a dihedral angle of 45.94 (16)°, while in molecule B this angle is 58.48 (16) °.

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link molecules into two crystallographically independent sets of chains propagated in direction [001].

Experimental

Benzohydrazide (5.0 mmol), ethanol (20 ml) and 2-chlorobenzaldehyde (5.0 mmol) were mixed in 50 ml flash. After refluxing for 3 h, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₁₄H_11ClN₂O: C 65.00, H 4.29, N 10.83%; found: C 65.13, H 4.36, N 10.74%.