1-Benzyl-2-phenyl-1H-benzimidazole–4,4′-(cyclo­hexane-1,1-di­yl)diphenol (1/1)

Chunhua Ge; Rui Zhang; Xiangdong Zhang; Su Li

doi:10.1107/S1600536811024007

. 2011 Jun 25;67(Pt 7):o1829. doi: 10.1107/S1600536811024007

1-Benzyl-2-phenyl-1H-benzimidazole–4,4′-(cyclohexane-1,1-diyl)diphenol (1/1)

Chunhua Ge ^a,^*, Rui Zhang ^a, Xiangdong Zhang ^a, Su Li ^a

PMCID: PMC3152116 PMID: 21837197

Abstract

The asymmetric unit of the title co-crystal, C₂₀H₁₆N₂·C₁₈H₂₀O₂, contains one molecule of 4,4′-(cyclohexane-1,1-diyl)diphenol (in which the cyclohexane ring adopts a chair conformation) and one molecule of 1-benzyl-2-phenyl-1H-benzimidazole, which are paired through an O—H⋯N hydrogen bond. These pairs are further linked by intermolecular O—H⋯O hydrogen bonds into chains along [010]. Weak intermolecular C—H⋯O and C—H⋯π interactions further consolidate the crystal packing. The dihedral angles between the pendant phenyl rings and the benzimidazole ring are 86.9 (2) and 43.1 (2)°.

Related literature

For the synthesis of 1,1-bis(4-hydroxyphenyl)cyclohexane, see: Yoshizawa et al.(2007 ▶). For related structures, see: Caira et al. (1995 ▶, 1997 ▶); Coupar et al. (1997 ▶); Lavy & Kaftory (2006 ▶); MacLean et al. (1999 ▶).

Experimental

Crystal data

C₂₀H₁₆N₂·C₁₈H₂₀O₂
M _r = 552.69
Triclinic,
a = 10.448 (3) Å
b = 10.853 (3) Å
c = 14.462 (4) Å
α = 102.518 (5)°
β = 94.156 (5)°
γ = 108.605 (5)°
V = 1499.5 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.982, T _max = 0.989
8312 measured reflections
5714 independent reflections
3748 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.140
S = 1.07
5714 reflections
381 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024007/cv5112sup1.cif

e-67-o1829-sup1.cif^{(23.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024007/cv5112Isup2.hkl

e-67-o1829-Isup2.hkl^{(279.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024007/cv5112Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	1.87	2.677 (3)	166
O2—H2⋯O1ⁱ	0.82	1.91	2.718 (3)	168
C29—H29⋯O2ⁱⁱ	0.93	2.64	3.467 (4)	148
C32—H32A⋯Cgⁱⁱⁱ	0.97	2.77	3.403 (4)	123

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant No. 20971062/B010303) and the Project for Provincial Key Laboratory of Liaoning Province, China (grant No. 2008S104).

supplementary crystallographic information

Comment

1,1-Bis(4-hydroxyphenyl)cyclohexane(BHC) is one of the most popular candidate for efficient and versatile synthesis of self-organized systems with specific properties and functions. The groups of BHC can participate in intermolecular hydrogen bonding, π···π and other interactions(for examples, see: Caira et al., 1995,1997; Coupar et al.,1997; Lavy & Kaftory, 2006; MacLean et al., 1999). BHC forms not only inclusion complex with neutral molecule but also supramolecular framework with the organic base. Here, we report the 1:1 cocrystal of BHC with 1-benzyl-2-phenyl-1H-benzo[d]imidazole(BPBI), a N-containing compound.

The asymmetric unit of the title cocrystal (Fig. 1) contains one molecule of BHC and one molecule of 1-benzyl-2-phenyl-1H-benzo[d]imidazole, which are paired through the O—H···N hydrogen bond (Table 1). These pairs are further linked by intermolecular O—H···O hydrogen bonds (Table 1) into chains in [010] (Fig. 2). Weak intermolecular C—H···O and C—H···π interactions (Table 1) consolidate further the crystal packing.

Experimental

1,1-Bis(4-hydroxyphenyl)cyclohexane (BHC) was synthesized according to the known procedure (Yoshizawa et al., 2007). To the BHC (0.1 mmol) in methanol (25 ml) was added 1-benzyl-2-phenyl-1H-benzo[d]imidazole (0.1 mmol) in methanol(5 ml) dropwise. The resulting mixture was stirred for 2 h at room temperature then filtered. Crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent in a few days.