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Volume 70 
Part 1 
Page o14  
January 2014  

Received 26 November 2013
Accepted 29 November 2013
Online 4 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.148
Data-to-parameter ratio = 17.8
Details
Open access

2-(4-Fluoro­phen­yl)-1-(3-meth­oxy­phen­yl)-4,5-dimethyl-1H-imidazole

aDepartment of Physics, Seethalakshmi Ramaswami College (Autonomous), Tiruchirappalli 620 002, India,bDepartment of Physics, K. Ramakrishnan College of Engineering, Samayapuram, Tiruchirappalli 621 112, India, and cDepartment of Chemistry, S.K.P. Engineering College, Thiruvanamalai 606 611, India
Correspondence e-mail: raghema2000@yahoo.co.in

In the title compound, C18H17FN2O, the imidazole ring makes dihedral angles of 68.81 (6) and 25.20 (8)° with the meth­oxy­phenyl and fluoro­phenyl rings, respectively. The dihedral angle between the meth­oxy­phenyl and fluoro­phenyl ring is 71.89 (6)°. In the crystal, mol­ecules are linked into inversion dimers with an R22(8) graph-set motif by pairs of weak C-H...F inter­actions.

Related literature

For related structures, see: Rizwana Begum et al. (2013[Rizwana Begum, S., Hema, R., Srinivasan, N. & Anitha, A. G. (2013). Acta Cryst. E69, o1154.]); Srinivasan et al. (2013[Srinivasan, N., Rizwana Begum, S. R. A., Hema, R., Sridhar, B. & Anitha, A. G. (2013). Acta Cryst. E69, o1599-o1600.]); Gayathri et al. (2010[Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o1703.]); Rosepriya et al. (2011[Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J., Srinivasan, N., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o1065.]). For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17FN2O

  • Mr = 296.34

  • Triclinic, [P \overline 1]

  • a = 8.1196 (5) Å

  • b = 9.6014 (6) Å

  • c = 10.6116 (6) Å

  • [alpha] = 106.818 (3)°

  • [beta] = 92.059 (3)°

  • [gamma] = 96.114 (3)°

  • V = 785.45 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.974, Tmax = 0.979

  • 15949 measured reflections

  • 3597 independent reflections

  • 2477 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.148

  • S = 1.03

  • 3597 reflections

  • 202 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15...F2i 0.93 2.55 3.437 (2) 160
Symmetry code: (i) -x, -y, -z-1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); 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: 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: HG5365 ).


Acknowledgements

SR thanks the University Grants Commission for financial support of this work (grant MRP-4335/12). The authors are thankful to the SAIF, IIT Madras, for the data collection.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o1703.  [CSD] [CrossRef] [IUCr Journals]
Rizwana Begum, S., Hema, R., Srinivasan, N. & Anitha, A. G. (2013). Acta Cryst. E69, o1154.  [CSD] [CrossRef] [IUCr Journals]
Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J., Srinivasan, N., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o1065.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Srinivasan, N., Rizwana Begum, S. R. A., Hema, R., Sridhar, B. & Anitha, A. G. (2013). Acta Cryst. E69, o1599-o1600.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o14  [ doi:10.1107/S1600536813032492 ]

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