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Volume 69 
Part 9 
Pages o1437-o1438  
September 2013  

Received 1 August 2013
Accepted 12 August 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.186
Data-to-parameter ratio = 18.5
Details
Open access

1-{2-(4-Chlorobenzyloxy)-2-[4-(morpholin-4-yl)phenyl]ethyl}-1H-benzimidazole propan-2-ol monosolvate

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, C26H26ClN3O2·C3H7OH, the benzimidazole ring system is essentially planar [maximum deviation = -0.018 (2) Å] and its mean plane is oriented with respect to the two benzene rings at dihedral angles of 4.51 (6) and 56.16 (6)°, and the dihedral angle between the two benzene rings is 59.11 (7)°. The morpholine ring displays a chair conformation. The propan-2-ol solvent molecule links with the benzimidazole ring via an O-H...N hydrogen bond. In the crystal, weak intermolecular C-H...O hydrogen bonds link the molecules into inversion dimers with an R22(28) motif. [pi]-[pi] stacking occurs between the parallel chlorobenzene rings [centroid-centroid distance = 3.792 (1) Å]. Weak C-H...[pi] interactions and short Cl...Cl [3.2037 (10) Å] contacts are 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.],d[Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008d). Acta Cryst. E64, o1655-o1656.], 2013[Özel Güven, Ö., Çapanlar, S., Adler, P. D. F., Coles, S. J. & Hökelek, T. (2013). Acta Cryst. E69, o147-o148.]); 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 ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For ring motif details, see: Bernstein et al. (1995[Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C26H26ClN3O2·C3H8O

  • Mr = 508.04

  • Triclinic, [P \overline 1]

  • a = 10.6542 (3) Å

  • b = 11.5152 (4) Å

  • c = 11.6853 (4) Å

  • [alpha] = 87.010 (3)°

  • [beta] = 83.703 (3)°

  • [gamma] = 71.572 (2)°

  • V = 1351.66 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 294 K

  • 0.30 × 0.28 × 0.25 mm

Data collection
  • Rigaku R-AXIS RAPID-S diffractometer

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011[Rigaku (2011). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.95, Tmax = 0.96

  • 17368 measured reflections

  • 6139 independent reflections

  • 3561 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.186

  • S = 1.11

  • 6139 reflections

  • 332 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.50 e Å-3

  • [Delta][rho]min = -0.53 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4-C9 benzene ring.

D-H...A D-H H...A D...A D-H...A
O3-H3A...N2i 0.85 (3) 2.08 (3) 2.916 (3) 170 (3)
C5-H5...O2ii 0.93 2.52 3.429 (3) 165
C2-H2B...Cg2i 0.97 2.68 3.465 (2) 138
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z.

Data collection: CrystalClear-SM Expert (Rigaku, 2011[Rigaku (2011). CrystalClear. 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: XU5728 ).


Acknowledgements

The authors acknowledge 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.  [CSD] [CrossRef] [details]
Özel Güven, Ö., Çapanlar, S., Adler, P. D. F., Coles, S. J. & Hökelek, T. (2013). Acta Cryst. E69, o147-o148.  [CSD] [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., Coles, S. J. & Hökelek, T. (2008d). Acta Cryst. E64, o1655-o1656.  [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.
Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979b). Acta Cryst. B35, 2461-2464.  [CSD] [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. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1437-o1438   [ doi:10.1107/S1600536813022599 ]

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