N′-(2-Chloro­benzyl­idene)-2-methyl­benzohydrazide

Wei-Guang Zhang

doi:10.1107/S1600536812000463

. 2012 Jan 11;68(Pt 2):o357. doi: 10.1107/S1600536812000463

N′-(2-Chlorobenzylidene)-2-methylbenzohydrazide

Wei-Guang Zhang ^a,^*

PMCID: PMC3275039 PMID: 22346984

Abstract

The title hydrazone compound, C₁₅H₁₃ClN₂O, adopts an E configuration about the C=N double bond. The dihedral angle between the two benzene rings is 13.1 (2)°. In the crystal, molecules are linked through N—H⋯O hydrogen bonds, forming chains parallel to [101].

Related literature

For the biological properties of hydrazone compounds, see: Ajani et al. (2010 ▶); Angelusiu et al. (2010 ▶); Zhang et al. (2010 ▶); Horiuchi et al. (2009 ▶). For the crystal structures of similar hydrazone comounds, see: Ban (2010 ▶); Hussain et al. (2010 ▶); Shalash et al. (2010 ▶); Khaledi et al. (2009 ▶). For the crystal structure of the 2-fluorobenzohydrazide analoque, reported on recently by the author, see: Zhang (2011 ▶).

Experimental

Crystal data

C₁₅H₁₃ClN₂O
M _r = 272.72
Monoclinic,
a = 7.4305 (17) Å
b = 25.596 (2) Å
c = 7.7926 (18) Å
β = 113.505 (2)°
V = 1359.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.947, T _max = 0.947
7513 measured reflections
2516 independent reflections
1870 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.141
S = 1.08
2516 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536812000463/qm2047sup1.cif

e-68-0o357-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000463/qm2047Isup2.hkl

e-68-0o357-Isup2.hkl^{(123.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812000463/qm2047Isup3.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
N2—H2⋯O1ⁱ	0.90 (1)	2.00 (1)	2.876 (3)	164 (3)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from Qiqihar University is acknowledged.

supplementary crystallographic information

Comment

Benzoylhydrazones are a kind of special Schiff bases bearing the –C(O)—NH—N=CH– groups. The hydrazone compounds have been received much attention for their excellent biological properties (Ajani et al., 2010; Angelusiu et al., 2010; Zhang et al., 2010; Horiuchi et al., 2009) as well as their crystal structures (Ban, 2010; Hussain et al., 2010; Shalash et al., 2010; Khaledi et al., 2009). Recently, the author has reported a hydrazone compound derived from the reaction of 2-chlorobenzaldehyde with 2-fluorobenzohydrazide (Zhang, 2011). In the present paper, the title new hydrazone compound, derived from the reaction of 2-chlorobenzaldehyde with 2-methylbenzohydrazide, is reported.

The compound adopts an E configuration about the C═N double bond (Fig. 1). The dihedral angle between the two substituted benzene rings is 13.1 (2)°. In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains parallel to the ac diagonal (Fig. 2).

Experimental

2-Chlorobenzaldehyde (0.140 g, 1 mmol) and 2-methylbenzohydrazide (0.150 g, 1 mmol) were mixed in 50 ml me thanol. The mixture was stirred and refluxed for 30 min and cooled to room temperature to give a colorless solution. Colorless block-shaped single crystals were obtained on slow evaporation of the solution in air.