1-(2,3-Dimeth­oxy­benzyl­idene)-2-(2,4-dinitro­phen­yl)hydrazine

Xianrong Xin; Min Li; Zhimin Chen; Ruitao Zhu

doi:10.1107/S1600536811013894

. 2011 Apr 16;67(Pt 5):o1169. doi: 10.1107/S1600536811013894

1-(2,3-Dimethoxybenzylidene)-2-(2,4-dinitrophenyl)hydrazine

Xianrong Xin ^a, Min Li ^a, Zhimin Chen ^a, Ruitao Zhu ^b,^*

PMCID: PMC3089222 PMID: 21754475

Abstract

In the title compound, C₁₅H₁₄N₄O₆, the dihedral angle between the aromatic rings is 3.7 (4)°. The nitro groups make dihedral angles of 6.0 (4) and 5.2 (4)° with the parent ring and are oriented at 6.0 (6)° with respect to each other. The methoxy groups are inclined at 54.0 (2) and 2.5 (3)° with respect to the benzene ring to which they are attached. In the crystal, molecules are linked by weak C—H⋯O interactions. The molecular conformation is consolidated by an intramolecular N—H⋯O hydrogen bond.

Related literature

For general background to the properties of Schiff base compounds, see: Mufakkar et al. (2010 ▶); Tahir et al. (2010 ▶). For related structures, see: Salhin et al. (2007 ▶); Tameem et al. (2008 ▶); Shao et al. (2008 ▶).

Experimental

Crystal data

C₁₅H₁₄N₄O₆
M _r = 346.30
Triclinic,
a = 7.8409 (8) Å
b = 7.9200 (9) Å
c = 13.8961 (14) Å
α = 85.038 (2)°
β = 82.773 (1)°
γ = 65.894 (1)°
V = 780.85 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.43 × 0.38 × 0.37 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.952, T _max = 0.958
4130 measured reflections
2725 independent reflections
1414 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.178
S = 1.06
2725 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013894/pv2405sup1.cif

e-67-o1169-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013894/pv2405Isup2.hkl

e-67-o1169-Isup2.hkl^{(133.8KB, hkl)}

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
N1—H1⋯O1	0.86	1.99	2.625 (4)	130
C14—H14A⋯O4ⁱ	0.96	2.48	3.431 (4)	170

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Professor Daqi Wang, Liaocheng University, for use of the X-ray diffraction facility.

supplementary crystallographic information

Comment

In view of the importance of hydrazone derivatives in chemical and biological applications (Shao et al., 2008), a series of hydrazone derivatives has been prepared, and several X-ray structures have been reported (Salhin et al., 2007; Aameem et al., 2008). Here, we report the crystal structure of the title compound.

The bond distances and bond angles in the title compound (Fig. 1) are in agreement with the corresponding bond distances and angles reported in the crystale structures of closely related compounds, (Salhin et al., 2007; Tameem et al., 2008). In the crystal structure (Fig. 2), the molecules are linked by C—H···O weak interactions (Table 1). The molecular conformation is consolidated by an intramolecular N—H···O hydrogen bonding interaction (Table 1).

Experimental

Equimolar quantities of 2,4-dinitrophenylhydrazine (0.99 g, 5.0 mmol) and 2,3-dimethoxybenzaldehyde (0.83 g, 5.0 mmol) were refluxed in ethanol (20 ml) for 30 min and rotary evaporated. The crystals of the title compound were growm by recrystallization from an ethanol solution.