2-Eth­oxy-6-[1-(3-eth­oxy-2-hy­droxy­benz­yl)-2,3-dihydro-1H-benzimidazol-2-yl]phenol acetonitrile monosolvate

Kwang Ha

doi:10.1107/S1600536812015449

. 2012 Apr 18;68(Pt 5):o1398. doi: 10.1107/S1600536812015449

2-Ethoxy-6-[1-(3-ethoxy-2-hydroxybenzyl)-2,3-dihydro-1H-benzimidazol-2-yl]phenol acetonitrile monosolvate

Kwang Ha ^a,^*

PMCID: PMC3344524 PMID: 22590286

Abstract

The title compound, C₂₄H₂₄N₂O₄·CH₃CN, a disubstituted benzimidazole, crystallized as an acetonitrile monosolvate. The benzene ring of the 2-ethoxy-6-methylphenol substiuent is approximately perpendicular to the nearly planar benzimidazole ring system [maximum deviation = 0.016 (1) Å], making a dihedral angle of 84.27 (8)°. The benzene ring of the 2-ethoxyphenol substituent is inclined to the benzimidazole mean plane by 29.68 (8)°. The dihedral angle between the benzene rings is 80.36 (9)°. In the molecule, there are strong O—H⋯N and O—H⋯O hydrogen bonds. In the crystal, molecules are connected by bifurcated O—H⋯(O,O) hydrogen bonds, forming chains propagating along [010].

Related literature

For the crystal structure of the methoxy derivative of the title compound, see: Al-Douh et al. (2009 ▶).

Experimental

Crystal data

C₂₄H₂₄N₂O₄·C₂H₃N
M _r = 445.51
Monoclinic,
a = 7.6177 (3) Å
b = 19.2728 (8) Å
c = 16.3480 (7) Å
β = 99.991 (1)°
V = 2363.72 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 K
0.27 × 0.24 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.853, T _max = 1.000
17475 measured reflections
5852 independent reflections
2912 reflections with I > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.129
S = 0.96
5852 reflections
309 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015449/su2405sup1.cif

e-68-o1398-sup1.cif^{(31.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015449/su2405Isup2.hkl

e-68-o1398-Isup2.hkl^{(286.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015449/su2405Isup3.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—H1O⋯N1	0.95 (3)	1.72 (3)	2.602 (2)	152 (2)
O3—H3O⋯O4	0.94 (3)	2.33 (3)	2.7180 (18)	103.9 (18)
O3—H3O⋯O1ⁱ	0.94 (3)	1.89 (3)	2.7774 (19)	158 (2)
O3—H3O⋯O2ⁱ	0.94 (3)	2.43 (3)	3.0117 (19)	119.7 (19)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2011–0030747).

supplementary crystallographic information

Comment

The crystal structure of the related compound, 2-methoxy-6-(1-(3-methoxy-2-hydroxybenzyl)-2,3-dihydro-1H-benzo[d]imidazol-2-yl)phenol monohydrate, has been reported on previously (Al-Douh et al., 2009).

The title compound contains a disubstituted benzimidazole molecule and a lattice solvent molecule (Fig. 1). One of the benzene rings (C17-C22) is approximately perpendicular to the nearly planar benzimidazole ring system [maximum deviation = 0.016 (1) Å], making a dihedral angle of 84.27 (8)°, whereas the other ring (C8-C13) is somewhat inclined to the benzomidazole mean plane with a dihedral angle of 29.68 (8)°. The dihedral angle between the benzene rings is 80.36 (9)°. The compound reveals strong intramolecular O—H···N and O—H···O hydrogen bonds, forming six- and five-membered rings, respectively (Fig. 1 and Table 1).

In the crystal, molecules are connected by bifurcated O—H···O,O hydrogen bonds, forming chains along the b axis (Fig. 2 and Table 1).

Experimental

1,2-Phenylenediamine (0.7568 g, 6.998 mmol) and 3-ethoxysalicylaldehyde (2.3269 g, 14.003 mmol) in EtOH (20 ml) were stirred for 5 h at room temperature. After evaporation of the solvent, the residue was recrystallized from a mixture of acetone and ether (1:2, v:v) at 188 K, to give an orange powder (1.9139 g). Orange block-like crystals, suitable for X-ray analysis, were obtained by slow evaporation of a CH₃CN/acetone solution at room temperature.