2-(2-Benzyl­oxyphen­yl)-1H-benzimid­azole

Navarrete-Vázquez, G.; Moreno-Diaz, H.; Estrada-Soto, S.; Tlahuext, H.

doi:10.1107/S1600536808004510

Volume 64
Part 3
Page o608
March 2008

Received 8 February 2008
Accepted 14 February 2008
Online 20 February 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.048
wR = 0.101
Data-to-parameter ratio = 6.7
Details

2-(2-Benzyloxyphenyl)-1H-benzimidazole

Gabriel Navarrete-Vázquez,^a Hermenegilda Moreno-Diaz,^a Samuel Estrada-Soto ^a and Hugo Tlahuext ^b ^*

^aFacultad de Farmacia, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001 Col., Chamilpa, CP 62100, Cuernavaca Mor., Mexico, and ^bCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001 Col., Chamilpa, CP 62100, Cuernavaca Mor., Mexico
Correspondence e-mail: tlahuext@ciq.uaem.mx

The asymmetric unit of the title compound, C₂₀H₁₆N₂O, contains two molecules. The dihedral angles between the benzimidazole ring systems and the attached benzene rings are 10.6 (5) and 13.7 (5)°. The conformers are linked by bifurcated three-centre hydrogen bonds, forming chains along the diagonal of the ab plane. The packing is further stabilized by [pi] - [pi] and C-H [pi] interactions.

Related literature

For general background, see: Desiraju & Steiner (1999); Lehn (1990); Saenger (1984); Wakelin (1986). For related structures, see: Estrada-Soto et al. (2006); Moreno-Diaz et al. (2006); Navarrete-Vázquez et al. (2006).

Experimental

Crystal data

C₂₀H₁₆N₂O
M_r = 300.35
Monoclinic, C c
a = 11.526 (2) Å
b = 17.210 (3) Å
c = 15.866 (3) Å
= 90.52 (3)°
V = 3147.0 (11) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 293 (2) K
0.31 × 0.21 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.976, T_max = 0.987
7808 measured reflections
2830 independent reflections
2691 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.100
S = 1.17
2830 reflections
423 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C27/N4/C26/C21/N3 imidazole ring, and Cg2, Cg3 and Cg4 are the centroids of the C28-C33, C15-C20 and C35-C40 benzene rings, respectively.

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.89 (4)	2.20 (3)	2.667 (4)	112 (3)
N1-H1N4ⁱ	0.89 (4)	2.18 (3)	3.008 (4)	154 (3)
N3-H3AO2	0.83 (4)	2.20 (5)	2.670 (4)	117 (4)
N3-H3AN2ⁱⁱ	0.83 (4)	2.18 (5)	2.918 (4)	148 (4)
C14-H14ACg1ⁱ	0.97	2.88	3.736 (4)	148
C14-H14BCg4ⁱⁱⁱ	0.97	2.92	3.721 (4)	141
Cg3Cg2ⁱ			3.859 (2)
Symmetry codes: (i) $[x-1, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z-1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus NT (Bruker, 2001); data reduction: SAINT-Plus NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2464 ).

Acknowledgements

This work was supported by the Consejo Nacional de Ciencia y Tecnología (CONACyT) under grant Nos. 3562P-E and PROMEP-SEP UAEMOR-PTC-131 (GNV).

References

Bruker (2000). SMART. Version 5.618. Bruker AXS Inc, Madison, Wisconsin, USA.
Bruker (2001). SAINT-Plus NT. Version 6.04. Bruker AXS Inc, Madison, Wisconsin, USA.
Desiraju, G. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, pp. 5-6. New York: Oxford University Press.
Estrada-Soto, S., Villalobos-Molina, R., Aguirre-Crespo, F., Vergara-Galicia, J., Moreno-Diaz, H., Torres-Piedra, M. & Navarrete-Vázquez, G. (2006). Life Sci. 79, 430-435.
Lehn, J.-M. (1990). Angew. Chem. Int. Ed. Engl. 29, 1304-1319.
Moreno-Diaz, H., Navarrete-Vázquez, G., Estrada-Soto, S. & Tlahuext, H. (2006). Acta Cryst. E62, o2601-o2602.
Navarrete-Vázquez, G., Moreno-Diaz, H., Aguirre-Crespo, F., León-Rivera, I., Villalobos-Molina, R., Muñoz-Muñiz, O. & Estrada-Soto, S. (2006). Bioorg. Med. Chem. Lett. 16, 4169-4173.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Wakelin, L. P. G. (1986). Med. Res. Rev. 6, 275-340.

organic compounds