(E)-N′-(3-Fluoro­benzyl­idene)-3-nitro­benzohydrazide

Xiao-Yan Li

doi:10.1107/S1600536812005478

. 2012 Feb 17;68(Pt 3):o697. doi: 10.1107/S1600536812005478

(E)-N′-(3-Fluorobenzylidene)-3-nitrobenzohydrazide

Xiao-Yan Li ^a,^*

PMCID: PMC3295477 PMID: 22412588

Abstract

In the title compound, C₁₄H₁₀FN₃O₃, the molecule exists in a trans conformation with respect to the methylidene unit. The dihedral angle between the benzene rings is 5.1 (2)°. In the crystal, molecules are linked through N—H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011 ▶); Lei (2011 ▶); Shalash et al. (2010 ▶). For the crystal structures of similar compounds, reported recently by the author, see: Li (2011a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₀FN₃O₃
M _r = 287.25
Monoclinic,
a = 11.823 (2) Å
b = 12.813 (3) Å
c = 8.7020 (17) Å
β = 94.855 (2)°
V = 1313.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.17 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.981, T _max = 0.983
9452 measured reflections
2429 independent reflections
1438 reflections with I > 2σ(I)
R _int = 0.075

Refinement

R[F ² > 2σ(F ²)] = 0.080
wR(F ²) = 0.218
S = 1.02
2429 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.22 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/S1600536812005478/rz2708sup1.cif

e-68-0o697-sup1.cif^{(15.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005478/rz2708Isup2.hkl

e-68-0o697-Isup2.hkl^{(119.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812005478/rz2708Isup3.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⋯O3ⁱ	0.90 (1)	1.96 (1)	2.846 (4)	172 (5)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author is grateful to the Zibo Vocational Institute for supporting this work.

supplementary crystallographic information

Comment

In recent years, hydrazone compounds have attracted much attention due to their syntheses and crystal structures (Hashemian et al., 2011; Lei, 2011; Shalash et al., 2010). As a continuation of our work on such compounds (Li, 2011a,b), the author reports herein on the crystal structure of the new title hydrazone compound.

The title compound (Fig. 1) exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the C1–C6 and C9–C14 benzene rings of the molecule is 5.1 (2)°. The N1/O1/O2 nitro group is tilted by 16.3 (3)° with respect to the C1—C6 benzene ring. In the crystal, molecules are linked through N–H···O hydrogen bonds (Table 1) to form chains along the c axis (Fig. 2).

Experimental

A mixture of 3-fluorobenzaldehyde (0.124 g, 1 mmol) and 3-nitrobenzohydrazide (0.181 g, 1 mmol) in 30 ml of ethanol containing few drops of acetic acid was refluxed for about 1 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from methanol. Yellow crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of the solvent.