1H-Benzimidazol-2-ylmethyl phenyl ether

Hassan, N.D.; Tajuddin, H.A.; Abdullah, Z.; Ng, S.W.

doi:10.1107/S1600536809007922

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 (C-C) = 0.009 Å
R = 0.046
wR = 0.111
Data-to-parameter ratio = 8.6
Details

1H-Benzimidazol-2-ylmethyl phenyl ether

Noor Doha Hassan,^a Hairul Anuar Tajuddin,^a Zanariah Abdullah ^a and Seik Weng Ng ^a ^*

^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-HN 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); Hassan et al. (2008); Idris et al. (2009); Shah Bakhtiar et al. (2009).

Experimental

Crystal data

C₁₄H₁₂N₂O
M_r = 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 radiation
= 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(I)
R_int = 0.091

Refinement

R[F² > 2(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
_max = 0.19 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N2ⁱ	0.88 (1)	2.03 (2)	2.879 (7)	163 (6)
N3-H3N4ⁱⁱ	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

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.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
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.
Idris, A., Afiffin, A., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o7.
Shah Bakhtiar, N., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o114.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2009). publCIF. In preparation.

organic compounds

1H-Benzimidazol-2-ylmethyl phenyl ether

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References