2-(1H-Benzimidazol-2-yl)-4-nitro­phenol

Jingya Sun; Xiangdi Tong

doi:10.1107/S1600536811001644

. 2011 Jan 15;67(Pt 2):o409. doi: 10.1107/S1600536811001644

2-(1H-Benzimidazol-2-yl)-4-nitrophenol

Jingya Sun ^a,^*, Xiangdi Tong ^a

PMCID: PMC3051601 PMID: 21523080

Abstract

The title compound, C₁₃H₉N₃O₃, was prepared by the reaction of 5-nitrosalicylaldehyde with 1,2-diaminobenzene in methanol. The whole molecule is approximately planar, with a mean deviation from the plane defined by the non-H atoms of 0.0311 (4) Å, and with a dihedral angle between the benzene ring and the benzimidazole ring system of 1.1 (3)°. An intramolecular O—H⋯N hydrogen bond occurs. In the crystal, adjacent molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For Schiff base compounds, see: Miura et al. (2009 ▶); Zhao et al. (2010 ▶); Karadağ et al. (2011) ▶; Bingöl Alpaslan et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₃H₉N₃O₃
M _r = 255.23
Monoclinic,
a = 8.117 (3) Å
b = 6.769 (2) Å
c = 20.842 (3) Å
β = 99.235 (2)°
V = 1130.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.978, T _max = 0.980
8933 measured reflections
2469 independent reflections
1283 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.153
S = 1.04
2469 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 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/S1600536811001644/hg2791sup1.cif

e-67-0o409-sup1.cif^{(15KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001644/hg2791Isup2.hkl

e-67-0o409-Isup2.hkl^{(121.3KB, 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⋯O2ⁱ	0.90 (1)	2.02 (1)	2.898 (3)	164 (3)
O1—H1⋯N1	0.82	1.85	2.590 (3)	149

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The condensation reaction between aldehydes with organic primary amines readily forms Schiff bases containing the typical –C=N– groups (Miura et al., 2009; Zhao et al., 2010; Karadağ et al., 2011; Bingöl Alpaslan et al., 2010). In this paper, the title compound (Fig. 1) was prepared by the reaction of 5-nitrosalicylaldehyde with 1,2-diaminobenzene in methanol.

The whole molecule of the compound is approximately planar, with mean deviation from the plane defined by the non-hydrogen atoms of 0.0311 (4) Å, and with the dihedral angle between the benzene ring and the Benzimidazole ring of 1.1 (3)°. All the bond lengths are within normal ranges (Allen et al., 1987). There is an intramolecular O—H···N hydrogen bond in the molecule (Table 1). In the crystal structure, adjacent two molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form a dimer (Fig. 2).

Experimental

5-Nitrosalicylaldehyde (1.0 mmol, 0.167 g) and 1,2-diaminobenzene (0.5 mmol, 0.054 g) were refluxed for 30 min in 30 ml me thanol, and cooled to room temperature to give colorless solid, which was isolated by filtration. Single crystals of the title compound were formed by recrystallization of the solid in methanol.