N′-(2-Hy­droxy-4-meth­oxy­benzyl­idene)-3-nitro­benzohydrazide

Chun-Bao Tang

doi:10.1107/S160053681104178X

. 2011 Oct 12;67(Pt 11):o2960. doi: 10.1107/S160053681104178X

N′-(2-Hydroxy-4-methoxybenzylidene)-3-nitrobenzohydrazide

Chun-Bao Tang ^a,^*

PMCID: PMC3247367 PMID: 22219985

Abstract

In the molecule of the title compound, C₁₅H₁₃N₃O₃, an intramolecular O—H⋯N hydrogen bond influences the planarity of the conformation; the dihedral angle between the benzene rings is 11.4 (3)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains in [101].

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶, 2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O₅
M _r = 315.28
Monoclinic,
a = 6.0099 (12) Å
b = 33.575 (3) Å
c = 7.319 (2) Å
β = 94.235 (2)°
V = 1472.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.28 × 0.23 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.970, T _max = 0.976
7720 measured reflections
3155 independent reflections
1786 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.140
S = 1.02
3155 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104178X/cv5171sup1.cif

e-67-o2960-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104178X/cv5171Isup2.hkl

e-67-o2960-Isup2.hkl^{(154.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681104178X/cv5171Isup3.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
O1—H1⋯N1	0.82	1.90	2.618 (2)	146
N2—H2⋯O3ⁱ	0.90 (1)	1.93 (1)	2.806 (2)	165 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the Jiaying University research fund is gratefully acknowledged.

supplementary crystallographic information

Comment

Hydrazone compounds have received much attention in biological and structural chemistry in the last years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010). Herewith we report the crystal structure of the title new hydrazone compound (I).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the similar compounds (Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010; Tang, 2010, 2011). Intramolecular O1—H1···N1 hydrogen bond generates a S(6) ring motif (Bernstein et al., 1995). The dihedral angle between the two benzene rings in the molecule is 11.4 (3)°.

In the crystal structure, the molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) into chains in [101] (Fig. 2).

Experimental

2-Hydroxy-4-methoxybenzaldehyde (0.1 mmol, 15.2 mg) and 3-nitrobenzohydrazide (0.1 mmol, 18.1 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear yellow solution. Yellow crystals of the compound were formed by slow evaporation of the solvent over several days.