Ethyl ({5-[5′-(2-eth­oxy-2-oxoeth­oxy)-4,4′′-difluoro-1,1′:3′,1′′-terphenyl-4′-yl]-1,3,4-oxadiazol-2-yl}sulfan­yl)acetate

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

doi:10.1107/S1600536812005028

Volume 68
Part 3
Pages o674-o675
March 2012

Received 26 January 2012
Accepted 5 February 2012
Online 10 February 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean () = 0.000 Å
Disorder in main residue
R = 0.061
wR = 0.196
Data-to-parameter ratio = 13.9
Details

Ethyl ({5-[5'-(2-ethoxy-2-oxoethoxy)-4,4''-difluoro-1,1':3',1''-terphenyl-4'-yl]-1,3,4-oxadiazol-2-yl}sulfanyl)acetate

Hoong-Kun Fun,^a ^*⁺ Suhana Arshad,^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, C₂₈H₂₄F₂N₂O₆S, the whole molecule is disordered over two sites with refined occupancies of 0.778 (3) and 0.222 (3). The central benzene ring makes dihedral angles of 56.0 (4), 34.5 (4) and 70.9 (4)°, respectively, with the two terminal benzene rings and the 1,3,4-oxadiazole ring in the major component of the disordered molecule. The corresponding angles in the minor component are 59.7 (16), 25.6 (13) and 75.5 (14)°. In the crystal, molecules are linked via C-HF, C-HN, C-HO and C-HS hydrogen bonds into a three-dimensional network. In addition, C-H [pi] interactions are observed.

Related literature

For a related structure and background to terphenyls and their oxadiazole derivatives, see: Fun, Arshad et al. (2011); Fun, Chia et al. (2011); Fun et al. (2012); Samshuddin et al. (2011). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₂₈H₂₄F₂N₂O₆S
M_r = 554.55
Triclinic, $[P \overline 1]$
a = 8.2721 (8) Å
b = 10.274 (1) Å
c = 16.2342 (16) Å
= 81.058 (2)°
= 82.987 (2)°
= 83.646 (2)°
V = 1346.8 (2) Å³
Z = 2
Mo K radiation
= 0.18 mm^-1
T = 100 K
0.42 × 0.24 × 0.12 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.928, T_max = 0.978
25187 measured reflections
7034 independent reflections
5142 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.196
S = 1.01
7034 reflections
506 parameters
99 restraints
H-atom parameters constrained
_max = 0.56 e Å^-3
_min = -0.66 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7-C9/C16/C17/C22 ring.

D-HA	D-H	HA	DA	D-HA
C8-H8AF1ⁱ	0.95	2.36	3.307 (8)	174
C15-H15AN2ⁱⁱ	0.95	2.45	3.266 (5)	144
C18-H18BO3ⁱⁱⁱ	0.99	2.38	3.200 (11)	140
C25-H25AF2^iv	0.99	2.46	3.112 (5)	123
C25-H25AO6^v	0.99	2.49	3.158 (9)	125
C27-H27BF2^vi	0.99	2.46	3.217 (7)	133
C28-H28CS1^v	0.98	2.85	3.700 (10)	146
C5-H5ACg1^vii	0.95	2.76	3.579 (6)	145
C18-H18ACg1ⁱⁱ	0.99	2.62	3.456 (10)	142
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+2, -z; (iii) -x+2, -y+2, -z; (iv) x, y, z+1; (v) -x+1, -y+1, -z+1; (vi) x-1, y, z+1; (vii) -x+1, -y+1, -z.

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: IS5061 ).

Acknowledgements

HKF and SA thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). SA thanks the Malaysian government and USM for the award of Academic Staff Training Scheme (ASTS). BN thanks the University Grants Commission (UGC) for financial assistance through SAP and BSR one time grant for the purchase of chemicals. SS thanks Mangalore University for the 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.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Fun, H.-K., Arshad, S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3372.
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. (2012). Acta Cryst. E68, o163.
Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Molbank, 2011, M745.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds