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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 [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.135
Data-to-parameter ratio = 17.8
Details
Open access

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

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-H...O hydrogen bonds link the molecules into inversion dimers. These dimers are further connected via weak C-H...N 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[Özel Güven, Ö., Erdogan, T., Göker, H. & Yildiz, S. (2007a). Bioorg. Med. Chem. Lett. 17, 2233-2236.],b[Özel Güven, Ö., Erdogan, T., Göker, H. & Yildiz, S. (2007b). J. Heterocycl. Chem. 44, 731-734.]). For related structures, see: Caira et al. (2004[Caira, M. R., Alkhamis, K. A. & Obaidat, R. M. (2004). J. Pharm. Sci. 93, 601-611.]); Freer et al. (1986[Freer, A. A., Pearson, A. & Salole, E. G. (1986). Acta Cryst. C42, 1350-1352.]); Özel Güven et al. (2008a[Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008a). Acta Cryst. E64, o1437.],b[Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008b). Acta Cryst. E64, o1496-o1497.],c[Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008c). Acta Cryst. E64, o1588-o1589.]); Peeters et al. (1979a[Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979a). Bull Soc. Chim. Belg. 88, 265-272.],b[Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979b). Acta Cryst. B35, 2461-2464.], 1996[Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1996). Acta Cryst. C52, 2225-2229.]). For hydrogen-bonding motifs, see: Bernstein et al. (1995[Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C26H27N3O2

  • Mr = 413.51

  • Triclinic, [P \overline 1]

  • a = 9.4719 (3) Å

  • b = 10.5057 (3) Å

  • c = 11.8110 (4) Å

  • [alpha] = 96.824 (3)°

  • [beta] = 108.953 (4)°

  • [gamma] = 98.312 (3)°

  • V = 1082.51 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.043

  • 3 standard reflections every 2 min intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.135

  • S = 1.06

  • 4972 reflections

  • 280 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.63 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-H...A D-H H...A D...A D-H...A
C5-H5...O2i 0.93 2.58 3.478 (2) 163
C6-H6...N3ii 0.93 2.56 3.439 (2) 159
C2-H2A...Cgiii 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[Rigaku (2011). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [ChemPort] [ISI]
Caira, M. R., Alkhamis, K. A. & Obaidat, R. M. (2004). J. Pharm. Sci. 93, 601-611.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Freer, A. A., Pearson, A. & Salole, E. G. (1986). Acta Cryst. C42, 1350-1352.  [CrossRef] [details]
Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008a). Acta Cryst. E64, o1437.  [CSD] [CrossRef] [details]
Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008b). Acta Cryst. E64, o1496-o1497.  [CSD] [CrossRef] [details]
Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008c). Acta Cryst. E64, o1588-o1589.  [CSD] [CrossRef] [details]
Özel Güven, Ö., Erdogan, T., Göker, H. & Yildiz, S. (2007a). Bioorg. Med. Chem. Lett. 17, 2233-2236.  [PubMed]
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.  [CrossRef] [ChemPort]
Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979b). Acta Cryst. B35, 2461-2464.  [CrossRef] [details] [ISI]
Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1996). Acta Cryst. C52, 2225-2229.  [CSD] [CrossRef] [details]
Rigaku (2011). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o147-o148   [ doi:10.1107/S1600536812051306 ]

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