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

Fun, H.-K.; Chia, T.S.; Samshuddin, S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S160053681105344X

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 (C-C) = 0.004 Å
Disorder in main residue
R = 0.057
wR = 0.171
Data-to-parameter ratio = 12.1
Details

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

Hoong-Kun Fun,^a ^*⁺ Tze Shyang Chia,^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, 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-HO 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); Samshuddin et al. (2011). For the synthesis, see: Kotnis (1990). For reference bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₂₂H₁₈F₂O₃
M_r = 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 radiation
= 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) T_min = 0.958, T_max = 0.986
11701 measured reflections
3036 independent reflections
2131 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.171
S = 1.10
3036 reflections
251 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C12-H12AO2ⁱ	0.93	2.59	3.515 (3)	179
C5-H5ACg3ⁱⁱ	0.93	2.92	3.589 (3)	130
C20-H20ACg2ⁱⁱⁱ	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); 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: 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.
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