N′-(3,5-Dichloro-2-hy­droxy­benzyl­idene)-4-nitro­benzohydrazide methanol solvate

Hai-Yun Zhu

doi:10.1107/S1600536810036184

. 2010 Sep 15;66(Pt 10):o2562. doi: 10.1107/S1600536810036184

N′-(3,5-Dichloro-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol solvate

Hai-Yun Zhu ^a,^*

PMCID: PMC2983133 PMID: 21587548

Abstract

In the title compound, C₁₄H₉Cl₂N₃O₄·CH₄O, the dihedral angle between the two benzene rings in the hydrazone molecule is 6.3 (3)°. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation. In the crystal, centrosymmetrically related molecules are linked through intermolecular O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For general background to hydrazone compounds, see: Rasras et al. (2010 ▶); Fan et al. (2010 ▶); Ajani et al. (2010 ▶); Avaji et al. (2009 ▶). For the crystal structures of related hydrazone compounds, see: Khaledi et al. (2010 ▶); Han et al. (2010 ▶); Hussain et al. (2010 ▶); Ji & Lu (2010 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₉Cl₂N₃O₄·CH₄O
M _r = 386.18
Monoclinic,
a = 7.415 (3) Å
b = 13.408 (3) Å
c = 16.674 (2) Å
β = 99.716 (3)°
V = 1634.0 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 298 K
0.15 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.938, T _max = 0.958
8410 measured reflections
3467 independent reflections
2099 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.124
S = 1.02
3467 reflections
232 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.31 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 datablocks global, I. DOI: 10.1107/S1600536810036184/rz2485sup1.cif

e-66-o2562-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036184/rz2485Isup2.hkl

e-66-o2562-Isup2.hkl^{(170.1KB, 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
O1—H1⋯N1	0.82	1.92	2.633 (3)	145
N2—H2⋯O5	0.90 (1)	1.91 (1)	2.793 (3)	167 (3)
O5—H5⋯O2ⁱ	0.82	2.15	2.903 (3)	153

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Science Research Foundation of Baoji University of Arts and Sciences (grant No. ZK085).

supplementary crystallographic information

Comment

In recent years, considerable interest has been focused on the preparation and biological properties of hydrazone compounds (Rasras et al., 2010; Fan et al., 2010; Ajani et al., 2010; Avaji et al., 2009). The crystal structures of a number of hydrazone compounds have been reported (Khaledi et al., 2010; Han et al., 2010; Hussain et al., 2010; Ji & Lu, 2010). The author reports in this paper the title new hydrazone compound.

The asymmetric unit of the title compound (Fig. 1) consists of a hydrazone molecule and a methanol molecule. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 6.3 (3)°. There is an intramolecular O—H···N hydrogen bond (Table 1) stabilizing the conformation of the hydrazone molecule. All bond lengths are within normal values (Allen et al., 1987), and are comparable with those in the similar hydrazone compounds as cited above. In the crystal structure (Fig. 2), centrosymmetrically related molecules are linked through intermolecular O—H···O and N—H···O hydrogen bonds (Table 1).

Experimental

3,5-Dichlorosalicylaldehyde (0.191 g, 1 mmol) and 4-nitrobenzohydrazide (0.181 g, 1 mmol) were dissolved in 30 ml absolute methanol. The mixture was stirred at reflux for 10 min, and cooled to room temperature. The clear yellow solution was left to slowly evaporate in air for a week, yielding yellow needle crystals of the title compound suitable for X-ray analysis.