N′-(3-Hy­droxy­benzyl­idene)-4-nitro­benzohydrazide

Chun-Hua Dai; Fu-Lin Mao

doi:10.1107/S1600536810043564

. 2010 Oct 31;66(Pt 11):o3004–o3005. doi: 10.1107/S1600536810043564

N′-(3-Hydroxybenzylidene)-4-nitrobenzohydrazide

Chun-Hua Dai ^a, Fu-Lin Mao ^a,^*

PMCID: PMC3009013 PMID: 21589165

Abstract

The title molecule, C₁₄H₁₁N₃O₄, is approximately planar, with an interplanar angle between the two benzene rings of 5.8 (2)°. In the crystal, four molecules are linked by an R ₄ ⁴(12) motif with pairs of strong O—H⋯O and N—H⋯O hydrogen bonds. The motif is situated about the crystallographic centres of symmetry and it is composed of two pairs of parallel molecules. This quadruplet of molecules is further extended by symmetry-equivalent hydrogen bonds to form layers parallel to the (10 Inline graphic ) plane. In addition to the hydrogen bonds, there is also a weak π–π interaction between the benzene rings.

Related literature

For medical applications of hydrazones, see: Ajani et al. (2010 ▶); Angelusiu et al. (2010 ▶); Zhang et al. (2010 ▶). For related structures, see: Ahmad et al. (2010 ▶); Huang & Wu (2010 ▶); Ji & Lu (2010 ▶); Khaledi et al. (2010 ▶); Singh & Singh (2010 ▶); Zhou & Yang (2010 ▶). For background to hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For hydrogen-bonding motifs, see: Etter et al. (1990 ▶). PLATON (Spek, 2009 ▶) was used to analyse the π–π interactions.

Experimental

Crystal data

C₁₄H₁₁N₃O₄
M _r = 285.26
Monoclinic,
a = 9.987 (3) Å
b = 8.967 (3) Å
c = 15.108 (4) Å
β = 106.560 (3)°
V = 1296.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.13 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.986, T _max = 0.989
6579 measured reflections
2768 independent reflections
1787 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.119
S = 1.03
2768 reflections
197 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 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/S1600536810043564/fb2226sup1.cif

e-66-o3004-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043564/fb2226Isup2.hkl

e-66-o3004-Isup2.hkl^{(135.9KB, 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
N2—H2⋯O1ⁱ	0.91 (2)	2.11 (2)	2.931 (2)	149.3 (16)
O1—H1⋯O2ⁱⁱ	0.85 (2)	1.82 (2)	2.6573 (17)	167 (2)

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Symmetry codes: (i) Inline graphic ; (ii) .

Table 2. Overview of π–π ring interactions in the structure.

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 benzene rings, respectively.

Centroid–centroid	Distance (Å)	Symmetry code
Cg1–Cg2	3.6803 (16)	1 − x, −y, 1 − z

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Acknowledgments

The authors acknowledge the Jiangsu Provincial Key Laboratory of Coastal Wetland Bioresources and Environmental Protection for open financial support (project No. JLCBE07026).

supplementary crystallographic information

Comment

In the last few months, a number of hydrazone compounds have been reported for their medical applications (Ajani et al., 2010; Angelusiu et al., 2010; Zhang et al., 2010). Recent structure analyses of some members of this family of compounds have also been reported (Ahmad et al., 2010; Huang & Wu, 2010; Ji & Lu, 2010; Khaledi et al., 2010; Singh & Singh, 2010; Zhou & Yang, 2010). In this paper, we report the structure of the new hydrazone compound, N'-(3-hydroxybenzylidene)-4-nitrobenzohydrazide.

The title molecule is shown in Fig. 1. The molecule is approximately planar, with the interplanar angle between the two benzene rings equal to 5.8 (2)°. The bond lengths and angles are comparable with the hydrazone compounds cited above.

Four title molecules are linked by the motif R₄⁴(12) (Etter et al., 1990) with pairs of strong O—H···O and strong N—H···O hydrogen bonds (Desiraju & Steiner, 1999). For the hydrogen bonds, see Table 1. The motif R₄⁴(12) is situated about the crystallographic centres of symmetry with the Wyckoff position 2c for the present setting. This motif is composed of two pairs of parallel molecules. This quadruplet of the title molecules is further extended by the symmetry equivalent H-bonds into the layers parallel to the planes (101). In addition to the hydrogen bonds there is also a weak π-electron ring–π-electron ring interaction (Table 2) between the benzene rings in the structure (Spek, 2009).

Experimental

4-Nitrobenzohydrazide (0.181 g, 1 mmol) and 3-hydroxybenzaldehyde (0.122 g, 1 mmol) were mixed in 50 ml of methanol at room temperature. The mixture was stirred at room temperature for 30 min to give a yellow solution of the product. After keeping the above solution in air for 5 d, yellow block-shaped crystals with average size of 0.1 mm × 0.2 mm × 0.2 mm developed.