(E)-4-Nitro-N′-(3-nitro­benzyl­idene)benzohydrazide

Xiao-Yan Li

doi:10.1107/S1600536812004540

. 2012 Feb 10;68(Pt 3):o655. doi: 10.1107/S1600536812004540

(E)-4-Nitro-N′-(3-nitrobenzylidene)benzohydrazide

Xiao-Yan Li ^a,^*

PMCID: PMC3295447 PMID: 22412558

Abstract

The title compound, C₁₄H₁₀N₄O₅, has an E conformation with respect to the C=N bond. The dihedral angle between the benzene rings is 2.41 (14)°. In the crystal, molecules are linked through N—H⋯O hydrogen bonds to form chains along the c axis. C—H⋯O interactions are also present, linking the chains to form a three-dimensional network.

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 on by the author, see: Li (2011a ▶,b ▶, 2012 ▶).

Experimental

Crystal data

C₁₄H₁₀N₄O₅
M _r = 314.26
Monoclinic,
a = 11.856 (2) Å
b = 14.116 (3) Å
c = 8.6263 (19) Å
β = 95.193 (2)°
V = 1437.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.981, T _max = 0.987
10319 measured reflections
2671 independent reflections
1288 reflections with I > 2σ(I)
R _int = 0.104

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.123
S = 0.84
2671 reflections
211 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 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/S1600536812004540/su2375sup1.cif

e-68-0o655-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004540/su2375Isup2.hkl

e-68-0o655-Isup2.hkl^{(131.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812004540/su2375Isup3.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—H2A⋯O3ⁱ	0.91 (2)	1.99 (2)	2.853 (3)	158 (2)
C6—H6⋯O1ⁱⁱ	0.93	2.57	3.369 (4)	145
C7—H7⋯O5ⁱⁱⁱ	0.93	2.56	3.287 (4)	135
C7—H7⋯O3ⁱ	0.93	2.53	3.271 (3)	137
C14—H14⋯O4ⁱⁱⁱ	0.93	2.40	3.246 (4)	151

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

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; Li, 2012), the author reports herein on the crystal structure of the new title hydrazone compound.

The title compound (Fig. 1) exists in an E conformation with respect to the C7═N1 bond. The dihedral angle between the (C1–C6) and (C9–C14) benzene rings is 2.41 (14) °.

In the crystal, molecules are linked through N–H···O hydrogen bonds to form chains along the c axis (Fig. 2 and Table 1). There are also C-H···O interactions present that link the chains to form a three-dimensional network (Table 1).

Experimental

A mixture of 3-nitrobenzaldehyde (0.151 g, 1 mmol) and 4-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 a solution of the title compound in methanol.