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Volume 68 
Part 1 
Page o172  
January 2012  

Received 2 December 2011
Accepted 12 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.057
wR = 0.171
Data-to-parameter ratio = 12.1
Details
Open access

Ethyl 4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-carboxylate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C22H18F2O3, the two fluoro-substituted rings form dihedral angles of 25.89 (15) and 55.00 (12)° with the central benzene ring. The ethoxy group in the molecule is disordered over two positions with a site-occupancy ratio of 0.662 (7):0.338 (7). In the crystal, molecules are linked by C-H...O hydrogen bonds into chains along the a axis. The crystal packing is further stabilized by C-H...[pi] and [pi]-[pi] interactions, with centroid-centroid distances of 3.8605 (15) Å.

Related literature

For a related structure and background to terphenyls, see: Fun et al. (2011[Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3390.]); Samshuddin et al. (2011[Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Molbank, M745.]). For the synthesis, see: Kotnis (1990[Kotnis, A. S. (1990). Tetrahedron Lett. 31, 481-484.]). For reference bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C22H18F2O3

  • Mr = 368.36

  • Orthorhombic, P 21 21 21

  • a = 8.5197 (11) Å

  • b = 9.5225 (12) Å

  • c = 22.871 (3) Å

  • V = 1855.5 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.43 × 0.21 × 0.15 mm

Data collection
  • Bruker APEX DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.958, Tmax = 0.986

  • 11701 measured reflections

  • 3036 independent reflections

  • 2131 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.171

  • S = 1.10

  • 3036 reflections

  • 251 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C7-C12 and C13-C18 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C12-H12A...O2i 0.93 2.59 3.515 (3) 179
C5-H5A...Cg3ii 0.93 2.92 3.589 (3) 130
C20-H20A...Cg2iii 0.96 2.83 3.710 (4) 152
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (ii) [-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x, y+{\script{3\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: RZ2682 ).


Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PSKBP/8630013). BN thanks the UGC for financial assistance through the SAP and BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3390.  [CSD] [CrossRef] [details]
Kotnis, A. S. (1990). Tetrahedron Lett. 31, 481-484.  [CrossRef] [ChemPort] [ISI]
Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Molbank, M745.
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 (2012). E68, o172  [ doi:10.1107/S160053681105344X ]

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