(E)-N′-(3-Fluoro­benzyl­idene)-4-methyl­benzohydrazide

Hua-Nan Hu; Shi-Yong Liu

doi:10.1107/S1600536812019484

. 2012 May 5;68(Pt 6):o1643. doi: 10.1107/S1600536812019484

(E)-N′-(3-Fluorobenzylidene)-4-methylbenzohydrazide

Hua-Nan Hu ^a, Shi-Yong Liu ^a,^*

PMCID: PMC3379245 PMID: 22719443

Abstract

In the title compound, C₁₅H₁₃FN₂O, the dihedral angle between the benzene rings is 16.9 (2)°. The F atom and the O atom are in a syn conformation. In the crystal, molecules are linked by N—H⋯O hydrogen bonds to generate C(4) chains propagating along the b-axis direction.

Related literature

For hydrazones that we have reported previously, see: Liu & You (2010 ▶); Liu & Wang (2010 ▶). For the crystal structures of other similar hydrazone compounds, see: Vijayakumar et al. (2009 ▶); Xu et al. (2009 ▶); Shafiq et al. (2009 ▶). graphic file with name e-68-o1643-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₃FN₂O
M _r = 256.27
Orthorhombic,
a = 13.2629 (5) Å
b = 7.9118 (3) Å
c = 24.9235 (8) Å
V = 2615.31 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.984, T _max = 0.986
26269 measured reflections
2424 independent reflections
1997 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.123
S = 1.04
2424 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019484/hb6775sup1.cif

e-68-o1643-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019484/hb6775Isup2.hkl

e-68-o1643-Isup2.hkl^{(119.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812019484/hb6775Isup3.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)	2.04 (1)	2.9322 (17)	169 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Zhejiang Provincial Natural Science Foundation of China (project No. Y12B020017).

supplementary crystallographic information

Comment

The crystal structures of hydrazones are of ongoing interest (Vijayakumar et al., 2009). As a continuation of our work on similar compounds (Liu & You, 2010; Liu & Wang, 2010), we report herein the crystal structure of the title compound a new hydrazone.

The molecular structure of the title compound is shown in Fig. 1. The two benzene ring system are inclined at a dihedral angle of 16.9 (2)°. All the bond lengths are comparable to those observed in related structures (Xu et al., 2009; Shafiq et al., 2009) and those we reported previously.

In the crystal structure, molecules are linked through N–H···O hydrogen bonds, to form one-dimensional chains running along the b axis (Fig. 2 and Table 1).

Experimental

The title compound was prepared by the condensation reaction of 3-fluorobenzaldehyde (0.05 mol, 6.2 g) and 4-methylbenzohydrazide (0.05 mol, 7.5 g) in anhydrous methanol (100 ml) at ambient temperature. Colourless blocks were obtained by slow evaporation of the solution for several days.