1-{2-Benz­yloxy-2-[4-(morpholin-4-yl)phen­yl]eth­yl}-1H-benzimidazole

Özel Güven, Ö.; Çapanlar, S.; Adler, P.D.F.; Coles, S.J.; Hökelek, T.

doi:10.1107/S1600536812051306

Volume 69
Part 1
Pages o147-o148
January 2013

Received 30 November 2012
Accepted 19 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.051
wR = 0.135
Data-to-parameter ratio = 17.8
Details

1-{2-Benzyloxy-2-[4-(morpholin-4-yl)phenyl]ethyl}-1H-benzimidazole

Özden Özel Güven,^a Seval Çapanlar,^a Philip D. F. Adler,^b Simon J. Coles ^b and Tuncer Hökelek ^c ^*

^aDepartment of Chemistry, Bülent Ecevit University, 67100 Zonguldak, Turkey,^bDepartment of Chemistry, Southampton University, SO17 1BJ Southampton, England, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

In the title compound, C₂₆H₂₇N₃O₂, the morpholine ring adopts a chair conformation. The benzene and phenyl rings are inclined to the benzimidazole mean plane by 7.28 (6) and 61.45 (4)°, respectively. In the crystal, pairs of weak C-HO hydrogen bonds link the molecules into inversion dimers. These dimers are further connected via weak C-HN hydrogen bonds. A weak C-H [pi] interaction is also observed.

Related literature

For general background to the biological activity of benzimidazole derivatives, see: Özel Güven et al. (2007a,b). For related structures, see: Caira et al. (2004); Freer et al. (1986); Özel Güven et al. (2008a,b,c); Peeters et al. (1979a,b, 1996). For hydrogen-bonding motifs, see: Bernstein et al. (1995). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₆H₂₇N₃O₂
M_r = 413.51
Triclinic, $[P \overline 1]$
a = 9.4719 (3) Å
b = 10.5057 (3) Å
c = 11.8110 (4) Å
= 96.824 (3)°
= 108.953 (4)°
= 98.312 (3)°
V = 1082.51 (7) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 100 K
0.32 × 0.25 × 0.22 mm

Data collection

Rigaku Saturn724+ diffractometer
13756 measured reflections
4972 independent reflections
3736 reflections with I > 2(I)
R_int = 0.043
3 standard reflections every 2 min intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.135
S = 1.06
4972 reflections
280 parameters
H-atom parameters constrained
_max = 0.63 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4-C9 benzene ring.

D-HA	D-H	HA	DA	D-HA
C5-H5O2ⁱ	0.93	2.58	3.478 (2)	163
C6-H6N3ⁱⁱ	0.93	2.56	3.439 (2)	159
C2-H2ACgⁱⁱⁱ	0.97	2.66	3.451 (2)	139
Symmetry codes: (i) -x, -y, -z; (ii) x, y, z+1; (iii) -x, -y+1, -z+1.

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5371 ).

Acknowledgements

The authors are grateful to Zonguldak Karaelmas University Research Fund (project No. 2010-13-02-06).

References

Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Caira, M. R., Alkhamis, K. A. & Obaidat, R. M. (2004). J. Pharm. Sci. 93, 601-611.
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Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Freer, A. A., Pearson, A. & Salole, E. G. (1986). Acta Cryst. C42, 1350-1352.
Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008a). Acta Cryst. E64, o1437.
Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008b). Acta Cryst. E64, o1496-o1497.
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Özel Güven, Ö., Erdogan, T., Göker, H. & Yildiz, S. (2007b). J. Heterocycl. Chem. 44, 731-734.
Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979a). Bull Soc. Chim. Belg. 88, 265-272.
Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979b). Acta Cryst. B35, 2461-2464.
Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1996). Acta Cryst. C52, 2225-2229.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds