4-Dimethyl­amino-N′-(4-nitro­benzyl­idene)benzohydrazide methanol monosolvate

Xiyue Zhang; Xiaobo Fu; Langzhu Tan; Chaixia Wang; Weixing Fan

doi:10.1107/S1600536812037063

. 2012 Sep 1;68(Pt 10):o2828. doi: 10.1107/S1600536812037063

4-Dimethylamino-N′-(4-nitrobenzylidene)benzohydrazide methanol monosolvate

Xiyue Zhang ^a,^*, Xiaobo Fu ^b, Langzhu Tan ^c, Chaixia Wang ^b, Weixing Fan ^a

PMCID: PMC3470190 PMID: 23125634

Abstract

In the title compound, C₁₆H₁₆N₄O₃·CH₃OH, the aromatic rings form a dihedral angle of 0.4 (2)°. The nitro group is twisted from the attached benzene ring by 7.5 (2)°. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link alternating hydrazone and methanol molecules into chains in [100]. The crystal packing exhibits π–π interactions between aromatic rings from neighbouring chains [centroid–centroid distances = 3.734 (3) and 3.903 (3) Å].

Related literature

For the biological activity of hydrazone compounds, see: Zhang et al. (2012 ▶); Cacic et al. (2006 ▶); Rauf et al. (2008 ▶); Bedia et al. (2006 ▶). For similar hydrazone compounds, see: Horkaew et al. (2012 ▶); Kargar et al. (2012 ▶); Hu & Liu (2012 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₆N₄O₃·CH₄O
M _r = 344.37
Triclinic,
a = 6.6621 (12) Å
b = 10.6685 (17) Å
c = 13.3437 (13) Å
α = 72.279 (2)°
β = 83.444 (2)°
γ = 73.984 (2)°
V = 867.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) ▶ T _min = 0.972, T _max = 0.978
6198 measured reflections
3140 independent reflections
2082 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.208
S = 1.08
3140 reflections
233 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.40 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/S1600536812037063/cv5333sup1.cif

e-68-o2828-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037063/cv5333Isup2.hkl

e-68-o2828-Isup2.hkl^{(154KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812037063/cv5333Isup3.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
O4—H4⋯O3	0.82	1.92	2.733 (2)	170
N2—H2⋯O4ⁱ	0.89 (1)	2.01 (1)	2.889 (2)	170 (2)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Hydrazones derived from the condensation reactions of hydrazines with carbonyl-containing compounds have been found to possess many biological activities, such as antibacterial, anticonvulsant, anti-inflamatory, and antitubercular (Zhang et al., 2012; Cacic et al., 2006; Rauf et al., 2008; Bedia et al., 2006). Recently, a number of hydrazones have been prepared and structurally characterized (Horkaew et al., 2012; Kargar et al., 2012; Hu & Liu, 2012). As an extension of work on the structural characterization of hydrazones, the title compound is reported here.

The asymmetric unit of the title compound contains a hydrazone molecule and a methanol molecule of crystallization linked by O—H···O hydrogen bond (Fig. 1). The hydrazone molecule displays a trans conformation with respect to the C=N bond. Two aromatic rings in the hydrazone molecules form a dihedral angle of 0.4 (2)°. The nitro group is twisted from the attached benzene ring at 7.5 (2)°. Intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) link alternating hydrazone and methanol molecules into chains in [100] (Fig. 2). The crystal packing exhibits π–π interactions between the aromatic ring from the neighbouring chains [centroid-centroid distances 3.734 (3), 3.903 (3) Å].

Experimental

4-Nitrobenzaldehyde (0.1 mmol, 15.1 mg) and 4-dimethylaminobenzhydrazide (0.1 mmol, 17.9 mg) were stirred in 20 ml methanol at room temperature for 30 min. A large number of small and yellow single crystals were formed by slow evaporation of the methanolic solution containing the compound in air.