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

Fun, H.-K.; Hemamalini, M.; Samshuddin, S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536811053037

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 (C-C) = 0.002 Å
R = 0.050
wR = 0.167
Data-to-parameter ratio = 21.6
Details

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

Hoong-Kun Fun,^a ^*⁺ Madhukar Hemamalini,^a S. Samshuddin,^b B. Narayana ^b and B. K. Sarojini ^c

^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-HO 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); Samshuddin et al. (2011). For chalcone derivatives of the title compound, see: Fun, Hemamalini et al. (2011); Betz et al. (2011a,b). For the synthetic procedure, see: Kotnis (1990). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₁H₁₆F₂O₂
M_r = 338.34
Monoclinic, P 2₁ /c
a = 6.0816 (7) Å
b = 25.997 (3) Å
c = 10.9061 (12) Å
= 100.866 (2)°
V = 1693.4 (3) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.930, T_max = 0.990
17519 measured reflections
4923 independent reflections
2883 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.167
S = 1.03
4923 reflections
228 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
C14-H14AO2	0.93	2.58	3.188 (2)	124
C19-H19ACg1ⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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.
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011a). Acta Cryst. E67, o2996-o2997.
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o3323-o3324.
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.
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3327-o3328.
Kotnis, A. S. (1990). Tetrahedron Lett. 31, 481-484.
Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Molbank, M745.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds