N′-(3-Fluoro­benzyl­idene)-2-methyl­benzohydrazide

Ying Song; Jian-Long Zhao; Jan-Gang Wang; Fei Lu; Hong Lu; Shi-Peng Li

doi:10.1107/S1600536812025548

. 2012 Jun 13;68(Pt 7):o2074. doi: 10.1107/S1600536812025548

N′-(3-Fluorobenzylidene)-2-methylbenzohydrazide

Ying Song ^a,^b, Jian-Long Zhao ^b, Jan-Gang Wang ^b, Fei Lu ^a, Hong Lu ^a,^*, Shi-Peng Li ^b

PMCID: PMC3393891 PMID: 22798756

Abstract

The asymmetric unit of the title compound, C₁₅H₁₃FN₂O, contains two independent molecules with different conformations; the two aromatic rings in the independent molecules form dihedral angles of 85.3 (2) and 10.0 (2)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into chains along [100].

Related literature

For related structures, see: Xu et al. (2011 ▶); Wang et al. (2012 ▶); Hu & Liu (2012 ▶). For the biological activity of benzohydrazones, see: Zhang et al. (2012 ▶).

Experimental

Crystal data

C₁₅H₁₃FN₂O
M _r = 256.27
Triclinic,
a = 7.8516 (13) Å
b = 8.1466 (13) Å
c = 21.158 (3) Å
α = 86.668 (2)°
β = 85.806 (2)°
γ = 79.772 (2)°
V = 1326.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.985, T _max = 0.986
9780 measured reflections
4844 independent reflections
4067 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.126
S = 1.06
4844 reflections
351 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536812025548/cv5308sup1.cif

e-68-o2074-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025548/cv5308Isup2.hkl

e-68-o2074-Isup2.hkl^{(237.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812025548/cv5308Isup3.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
N4—H4⋯O1	0.89 (1)	1.93 (1)	2.8115 (15)	168 (2)
N2—H2⋯O2ⁱ	0.89 (1)	2.08 (1)	2.9185 (16)	157 (2)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Benzohydrazones derived from the condensation reactions of benzohydrazides with carbonyl-containing compounds have been proved to have antimicrobial and antitumor activities (Zhang et al., 2012). Herewith we present the title compound (I), which is a new benzohydrazone derivative.

The asymmetric unit of the title compound contains two independent molecules, A and B, respectively, with different conformations (Fig. 1) - two aromatic rings in the independent molecules form the dihedral angles of 85.3 (2)° (B) and 10.0 (2)° (A), respectively. All the bond lengths and angles are normal and correspond to those observed in the related structures (Wang et al., 2012; Hu & Liu, 2012; Xu et al., 2011). In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains in [100] (Fig. 2).

Experimental

Equimolar quantities (1 mmol each) of 3-fluorohlorobenzaldehyde and 2-methylbenzohydrazide were mixed in 50 mL methanol. The materials were stirred at room temperature for 1 h to give a clear colorless solution. Colourless block-like single crystals were obtained after a few days.