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Volume 68 
Part 1 
Page o163  
January 2012  

Received 2 December 2011
Accepted 9 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.167
Data-to-parameter ratio = 21.6
Details
Open access

1-(4,4''-Difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl)ethanone

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 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, C21H16F2O2, the central benzene ring is inclined at dihedral angles of 30.91 (8) and 46.88 (7)° to the two terminal fluoro-substituted rings. The dihedral angle between the two terminal fluoro-subsituted rings is 68.34 (8)°. An intramolecular C-H...O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by weak C-H...[pi] interactions.

Related literature

For a related structure and background to terphenyls, see: Fun, Chia 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 chalcone derivatives of the title compound, see: Fun, Hemamalini et al. (2011[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3327-o3328.]); Betz et al. (2011a[Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011a). Acta Cryst. E67, o2996-o2997.],b[Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o3323-o3324.]). For the synthetic procedure, see: Kotnis (1990[Kotnis, A. S. (1990). Tetrahedron Lett. 31, 481-484.]). For hydrogen-bond 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
  • C21H16F2O2

  • Mr = 338.34

  • Monoclinic, P 21 /c

  • a = 6.0816 (7) Å

  • b = 25.997 (3) Å

  • c = 10.9061 (12) Å

  • [beta] = 100.866 (2)°

  • V = 1693.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.74 × 0.31 × 0.10 mm

Data collection
  • Bruker APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.930, Tmax = 0.990

  • 17519 measured reflections

  • 4923 independent reflections

  • 2883 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.167

  • S = 1.03

  • 4923 reflections

  • 228 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C14-H14A...O2 0.93 2.58 3.188 (2) 124
C19-H19A...Cg1i 0.96 2.80 3.6432 (19) 147
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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: RZ2681 ).


Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. 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

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011a). Acta Cryst. E67, o2996-o2997.  [CSD] [CrossRef] [details]
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o3323-o3324.  [CrossRef] [details]
Bruker (2009). APEX2, SAINT and SADABS. 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]
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3327-o3328.  [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, o163  [ doi:10.1107/S1600536811053037 ]

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