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Volume 65 
Part 4 
Page o733  
April 2009  

Received 2 March 2009
Accepted 4 March 2009
Online 11 March 2009

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.009 Å
R = 0.046
wR = 0.111
Data-to-parameter ratio = 8.6
Details
Open access

1H-Benzimidazol-2-ylmethyl phenyl ether

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

There are two molecules in the asymmetric unit of the title compound, C14H10N2O: the dihedral angles between their aromatic ring planes are 47.4 (4) and 46.8 (3)°. In the crystal structure, molecules are linked by N-H...N hydrogen bonds from the secondary nitrogen N-H donor to the tertiary N-atom acceptor of a symmetry-related neighbour, resulting in hydrogen-bonded chains. The two independent chains both propagate in [100].

Related literature

For related phenoxy-substituted N-heterocycles, see: Abdullah & Ng (2008[Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2165.]); Hassan et al. (2008[Hassan, N. D., Tajuddin, H. A., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o1820.]); Idris et al. (2009[Idris, A., Afiffin, A., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o7.]); Shah Bakhtiar et al. (2009[Shah Bakhtiar, N., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o114.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12N2O

  • Mr = 224.26

  • Orthorhombic, P c a 21

  • a = 10.0299 (5) Å

  • b = 8.5391 (4) Å

  • c = 27.000 (1) Å

  • V = 2312.5 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 120 K

  • 0.40 × 0.10 × 0.03 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: none

  • 15022 measured reflections

  • 2699 independent reflections

  • 1783 reflections with I > 2[sigma](I)

  • Rint = 0.091

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.111

  • S = 1.00

  • 2699 reflections

  • 313 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.88 (1) 2.03 (2) 2.879 (7) 163 (6)
N3-H3...N4ii 0.88 (1) 1.97 (2) 2.845 (8) 172 (5)
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+2, z]; (ii) [x-{\script{1\over 2}}, -y+1, z].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2923 ).


Acknowledgements

We thank the University of Malaya for supporting this study (FS358/2008 A).

References

Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2165.  [CSD] [CrossRef] [details]
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hassan, N. D., Tajuddin, H. A., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o1820.  [CSD] [CrossRef] [details]
Idris, A., Afiffin, A., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o7.  [CSD] [CrossRef] [details]
Shah Bakhtiar, N., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o114.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2009). publCIF. In preparation.


Acta Cryst (2009). E65, o733  [ doi:10.1107/S1600536809007922 ]

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