N′-(5-Hydr­oxy-2-nitro­benzyl­idene)-2-methoxy­benzohydrazide

De-Suo Yang

doi:10.1107/S1600536809043840

. 2009 Oct 28;65(Pt 11):o2864. doi: 10.1107/S1600536809043840

N′-(5-Hydroxy-2-nitrobenzylidene)-2-methoxybenzohydrazide

De-Suo Yang ^a,^*

PMCID: PMC2971021 PMID: 21578451

Abstract

The asymmetric unit of the title compound, C₁₅H₁₃N₃O₅, contains two independent molecules. Each molecule displays an E configuration with respect to its C=N double bond. The dihedral angles between the two benzene rings are 11.1 (2) and 10.9 (2)° in the two molecules. In the crystal structure, molecules are linked through intermolecular O—H⋯O hydrogen bonds, forming chains running along the a axis.

Related literature

For the biological and structural chemistry of hydrazone compounds, see: Avaji et al. (2009 ▶); Charkoudian et al. (2007 ▶); Cukurovali et al. (2006 ▶). For related structures, see: Yang (2008a ▶,b ▶,c ▶,d ▶,e, 2007a ▶,b ▶,c ▶); Yang & Guo (2006 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O₅
M _r = 315.28
Triclinic,
a = 8.7540 (9) Å
b = 9.0529 (9) Å
c = 18.2159 (17) Å
α = 86.902 (5)°
β = 83.023 (5)°
γ = 82.509 (5)°
V = 1419.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.981, T _max = 0.983
8779 measured reflections
6066 independent reflections
4236 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.123
S = 1.04
6066 reflections
425 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809043840/wn2358sup1.cif

e-65-o2864-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043840/wn2358Isup2.hkl

e-65-o2864-Isup2.hkl^{(296.9KB, 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
O5—H5⋯O6ⁱ	0.82	1.91	2.721 (2)	169
O10—H10⋯O1	0.82	1.88	2.689 (2)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges Baoji University of Arts and Sciences for support.

supplementary crystallographic information

Comment

Hydrazone compounds have been of great interest for a long time. These compounds play an important role in biological and structural chemistry (Avaji et al., 2009; Charkoudian et al., 2007; Cukurovali et al., 2006). Recently, we have reported a few hydrazone compounds (Yang, 2008a,b,c,d,e, 2007a,b,c; Yang & Guo, 2006). As a further investigation in this area, the crystal structure of the new title hydrazone compound is reported.

The asymmetric unit of the title compound, Fig. 1, consists of two independent molecules. Each molecule displays an E configuration with respect to the C═N double bond. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 11.1 (2)°, and that between the C16—C21 and C24—C29 benzene rings is 10.9 (2)°. All the bond lengths are within normal ranges (Allen et al., 1987). The C7═N1 and C22═N4 bond lengths of 1.256 (2) and 1.260 (2) Å, respectively, conform to the values for double bonds. The bond length of 1.348 (2) Å between atoms C8 and N2, and that of 1.351 (2) Å between atoms C23 and N5, are intermediate between C—N single bonds and C═N double bonds, because of conjugation effects in the molecules.

In the crystal structure, molecules are linked through intermolecular O—H···O hydrogen bonds (Table 1), forming chains running along the a axis (Fig. 2).

Experimental

5-Hydroxy-2-nitrobenzaldehyde (0.1 mmol, 16.7 mg) and 2-methoxybenzohydrazide (0.1 mmol, 16.6 mg) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature to give a clear colorless solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of 5 days at room temperature.