3-[1-(3-Hy­droxy­benz­yl)-1H-benzimid­azol-2-yl]phenol dimethyl sulfoxide monosolvate

Magdalena Quezada-Miriel; Alcives Avila-Sorrosa; Juan Manuel German-Acacio; Reyna Reyes-Martínez; David Morales-Morales

doi:10.1107/S1600536812040275

. 2012 Sep 29;68(Pt 10):o3053–o3054. doi: 10.1107/S1600536812040275

3-[1-(3-Hydroxybenzyl)-1H-benzimidazol-2-yl]phenol dimethyl sulfoxide monosolvate

Magdalena Quezada-Miriel ^a, Alcives Avila-Sorrosa ^a, Juan Manuel German-Acacio ^b, Reyna Reyes-Martínez ^a, David Morales-Morales ^a,^*

PMCID: PMC3470402 PMID: 23125815

Abstract

Crystals of the title compound were obtained as a 1:1 dimethyl sulfoxide solvate, C₂₀H₁₆N₂O₂·C₂H₆O. The molecular conformation of the organic molecule is similar to that in the previously reported unsolvated structure [Eltayeb et al. (2009 ▶). Acta Cryst. E65, o1374–o1375]. Thus, the dihedral angles formed by the benzimidazole moiety with the two benzene rings are 57.54 (4) and 76.22 (5)°, and the dihedral angle between the benzene rings is 89.23 (5)°. In the crystal, a three-dimensional network features O—H⋯O, O—H⋯N and O—H⋯S hydrogen bonds, as well as C—H⋯O and C—H⋯π interactions.

Related literature

For potential applications of benzimidazoles in medicine, see: Narasimhan et al. (2012 ▶); Alper et al. (2003 ▶); Sharma et al. (2011 ▶). For coordination compounds of benzimidazole derivatives, see: Tellez et al. (2008 ▶). For the crystal structure of 3-[1-(3-hydroxybenzyl)-1H-benzimidazol-2-yl]phenol, see: Eltayeb et al. (2009 ▶).

Experimental

Crystal data

C₂₀H₁₆N₂O₂·C₂H₆OS
M _r = 394.48
Triclinic,
a = 8.892 (1) Å
b = 9.1951 (10) Å
c = 13.1515 (14) Å
α = 85.399 (2)°
β = 71.947 (2)°
γ = 77.442 (2)°
V = 997.81 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 298 K
0.36 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: analytical (SHELXTL; Sheldrick, 2008 ▶) T _min = 0.618, T _max = 0.752
8327 measured reflections
3656 independent reflections
2912 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.113
S = 1.00
3656 reflections
261 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.32 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 datablock(s) I, global. DOI: 10.1107/S1600536812040275/tk5153sup1.cif

e-68-o3053-sup1.cif^{(27.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040275/tk5153Isup2.hkl

e-68-o3053-Isup2.hkl^{(179.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812040275/tk5153Isup3.cml

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

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

Cg1, Cg2 and Cg3 are the centroids of the C4–C9, C11–C16 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.85 (1)	1.83 (1)	2.6804 (19)	176 (2)
O2—H2⋯S1ⁱ	0.85 (1)	2.84 (1)	3.6209 (14)	154 (2)
O1—H1⋯N3ⁱⁱ	0.86 (1)	1.88 (2)	2.7316 (19)	172 (2)
C18—H18⋯O3ⁱ	0.93	2.58	3.260 (2)	130
C23—H23C⋯O3ⁱⁱⁱ	0.96	2.72	3.643 (3)	162
C10—H10B⋯Cg1^iv	0.97	2.95	3.622 (2)	127
C5—H5⋯Cg2^v	0.93	2.76	3.624 (2)	156
C23—H23B⋯Cg3^vi	0.96	2.86	3.679 (2)	144

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

Acknowledgments

MQM (BSc), AAS (PhD) and RRM (postdoctoral agreement No. 290586 UNAM) would like to thank CONACYT for scholarships. DMM would like to acknowledge Dr Simón Hernández-Ortega for technical assistance. The financial support of this research by CONACYT (CB2010–154732) and DGAPA-UNAM (IN201711) is gratefully acknowledged. JMGA would like to thank the Departamento de Ciencias Básicas e Ingeniería de la UAM Campus Lerma for the generous financial support.

supplementary crystallographic information

Comment

Benzimidazole and its derivatives are of significant importance in medicinal chemistry. In these species, the presence of the benzimidazole heterocycle provides a vast variety of potential biological and clinical applications (Narasimhan et al., 2012). Benzimidazole derivatives with potential biological activities have been widely studied for the treatment of different illnesses such as cancer (Alper et al., 2003), infectious diseases, metabolic and cardiovascular disorders, allergies, tuberculosis (Sharma et al., 2011) and different inflammatory conditions. Thus, in order to increase the activity of benzimidazole derivatives its coordination behaviour with transition metals such as Pd(II), Co(II), Ni(II), Cu(II) and Cd(II) (Tellez et al., 2008) has been explored.

The crystal structure of 3-[1-(3-hydroxybenzyl)-1H-benzimidazol-2-yl]phenol was first reported by Eltayeb et al. (2009). Thus, in this opportunity we would like to report the DMSO solvated structure of 3-[1-(3-hydroxybenzyl)-1H-benzimidazol-2-yl]phenol (Fig. 1).

In this molecule, the dihedral angles formed by the benzimidazole moiety with the two benzene rings (C11–C16 and C17–C22) are 57.54 (4) and 76.22 (5)° respectively. The two benzene rings (C11–C16 and C17–C22) are forming a dihedral angle of 89.23 (5)°, these values are similar to those reported previously (Eltayeb et al. 2009).

The crystal lattice of the title compound is stabilized by the presence of hydrogen bonds (O—H···N, O—H···O, O—H···S, C—H···O and C—H···π), Table 1. The O—H···N interactions associate two molecules to generate an 18-membered macrocycle with crystallographic inversion symmetry, that are interconnected each other by C—H···π interactions between methylene (C10—H10B) group and the aromatic ring (C4—C9) of the neighbouring molecules, Fig. 2. The C5—H5···π and O—H···O interactions stabilize the three-dimensional arrangement. Finally, the DMSO molecules are associate by C—H···O interactions thus generating eight-membered motifs, by additionally exhibiting interactions with the benzimidazole of the type O2—H2···S1.

Experimental

To a solution of 3-hydroxybenzaldehyde (0.320 g, 2.0 mmol) in CH₂Cl₂, 0.034 g (0.2 mmol) of p-toluenesulfonic acid, 0.7 g of o-phenylenediamine (6.4 mmol) and molecular sieves were added. The mixture was stirred at room temperature for 24 h. After this time the resulting solution was filtered and the solvent evaporated under vacuum affording 3-[1-(3-Hydroxybenzyl)-1H-benzimidazol-2-yl]phenol as a microcrystalline white powder. Single crystals suitable for X-ray diffraction analysis were obtained from a dimethyl sulfoxide solution of the compound.