4-[1-(4-Hy­droxy-3-meth­oxy­benz­yl)-1H-benzimidazol-2-yl]-2-meth­oxy­phenol

Zuo-an Xiao; Tao Gao; Fa-jun Huang; Ting-ting Jiang

doi:10.1107/S1600536811043935

. 2011 Oct 29;67(Pt 11):o3087. doi: 10.1107/S1600536811043935

4-[1-(4-Hydroxy-3-methoxybenzyl)-1H-benzimidazol-2-yl]-2-methoxyphenol

Zuo-an Xiao ^a,^*, Tao Gao ^a, Fa-jun Huang ^a, Ting-ting Jiang ^a

PMCID: PMC3247474 PMID: 22220092

Abstract

In the title molecule, C₂₂H₂₀N₂O₄, the dihedral angles between the benzimidazole ring system and the benzene rings are 44.26 (2) and 82.91 (2)°. Intramolecular O—H⋯O hydrogen bonds occur. In the crystal, O—H⋯N and O—H⋯O hydrogen bonds connect the molecules into a two-dimension network parallel to (10 Inline graphic ) and weak intermolecular C—H⋯O hydrogen bonds complete the formation of a three-dimensional network.

Related literature

For the biological appications of benzimidazole compounds, see: Santoro et al. (2000 ▶); Sundberg et al. (1977 ▶). For related structures, see: Li et al. (2005 ▶); Liu et al. (2003 ▶); Xi et al. (2006 ▶).

Experimental

Crystal data

C₂₂H₂₀N₂O₄
M _r = 376.40
Monoclinic,
a = 7.9717 (9) Å
b = 16.4327 (19) Å
c = 14.3560 (16) Å
β = 95.133 (2)°
V = 1873.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.966, T _max = 0.983
14067 measured reflections
4625 independent reflections
3718 reflections with I > 2σ(I)
R _int = 0.064

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.154
S = 1.06
4625 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043935/lh5356sup1.cif

e-67-o3087-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043935/lh5356Isup2.hkl

e-67-o3087-Isup2.hkl^{(226.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811043935/lh5356Isup3.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
O4—H4A⋯O3	0.89 (2)	2.25 (2)	2.6598 (18)	108.0 (18)
O1—H1A⋯O2	0.85 (3)	2.22 (3)	2.6631 (18)	113 (2)
O4—H4A⋯N2ⁱ	0.89 (2)	1.90 (2)	2.7671 (18)	165 (2)
O1—H1A⋯O4ⁱⁱ	0.85 (3)	2.07 (3)	2.7934 (17)	143 (2)
C15—H15B⋯O4ⁱⁱⁱ	0.97	2.59	3.402 (2)	141

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

Acknowledgments

The authors are grateful to the Science Technology Research Programme of the Education Office of Hubei Province (grant No. Q20092503) for financial support.

supplementary crystallographic information

Comment

Benzimidazole is a common species in biological and biochemical structures (Sundberg et al., 1977; Santoro et al., 2000). Many benzimidazole derivatives have already been reported (e.g. Liu et al., 2003; Li et al., 2005; Xi et al., 2006) and the preparation of the title compound, (I), is part of our effort to contribute to this research. Herein we report the crystal structure of (I).

In the molecule (Fig. 1) the dihedral angles between the benzimidazole ring system and the benzene rings are [C8-C13] 44.26 (2)° and [C16-C21] 82.91 (2)°. All bond lengths and bond angles are as expected. In the crystal, (Fig.2) molecules are linked by O—H···N and O—H···O and weak C—H···O hydrogen bonds to form a three-dimensional network.

Experimental

3-Methoxy-4-hydroxyphenyl formaldehyde (10 mmol) and 1,2-diaminobenzene(5 mmol) were mixed in hot water (333 K), the resulting mixture was stirred and refluxed for 3 h at 333 K. The solution was filtered, and the resulting yellow precipitate was recystallized from methanol to obtain pure product. Yellow crystals suitable for an X-ray diffraction study were obtained by slow evaporation of methanol and dimethyl sulfoxide (1:1 v/v) for two months.