(2E)-3-(4-Cyano­phen­yl)-1-(4,4′′-difluoro-5′-meth­oxy-1,1′:3′,1′′-terphenyl-4′-yl)prop-2-en-1-one

Hoong-Kun Fun; Wan-Sin Loh; S Samshuddin; B Narayana; B K Sarojini

doi:10.1107/S1600536812023124

. 2012 May 26;68(Pt 6):o1877–o1878. doi: 10.1107/S1600536812023124

(2E)-3-(4-Cyanophenyl)-1-(4,4′′-difluoro-5′-methoxy-1,1′:3′,1′′-terphenyl-4′-yl)prop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Wan-Sin Loh ^a,^§, S Samshuddin ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3379440 PMID: 22719638

Abstract

In the title compound, C₂₉H₁₉F₂NO₂, the central benzene ring forms a dihedral angle of 56.92 (12)° with the cyanobenzene ring and dihedral angles of 40.91 (12) and 44.76 (12)° with the two fluorobenzene rings. In the crystal, C—H⋯O and C—H⋯F hydrogen bonds link the molecules into sheets lying parallel to the ab plane. The crystal packing also features C—H⋯π interactions involving the central benzene ring.

Related literature

For background to terphenyls, see: Fun, Hemamalini et al. (2011 ▶); Fun, Shahani et al. (2011 ▶); Fun et al. (2012 ▶); Betz et al. (2011 ▶). For a related structure, see: Fun, Chia et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). graphic file with name e-68-o1877-scheme1.jpg

Experimental

Crystal data

C₂₉H₁₉F₂NO₂
M _r = 451.45
Triclinic,
a = 6.9656 (2) Å
b = 11.2404 (3) Å
c = 14.6014 (3) Å
α = 96.108 (1)°
β = 90.415 (1)°
γ = 104.764 (1)°
V = 1098.51 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.34 × 0.20 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.968, T _max = 0.989
17054 measured reflections
3828 independent reflections
2982 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.112
S = 1.03
3828 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023124/hb6802sup1.cif

e-68-o1877-sup1.cif^{(31KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023124/hb6802Isup2.hkl

e-68-o1877-Isup2.hkl^{(187.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812023124/hb6802Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O1ⁱ	0.95	2.40	3.213 (3)	143
C29—H29A⋯F2ⁱⁱ	0.98	2.54	3.447 (3)	155
C29—H29B⋯Cg1ⁱⁱⁱ	0.98	2.75	3.521 (3)	136

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). 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 the research facilities.

supplementary crystallographic information

Comment

In continuation of our work on synthesis of terphenyl chalcones (Fun, Hemamalini et al., 2011; Fun, Shahani et al., 2011; Betz et al., 2011), the title compound is prepared and its crystal structure is reported. The starting material of the title compound was prepared from 4,4'-difluoro chalcone by several steps (Fun et al., 2012).

In the title compound (Fig. 1), the central benzene ring (C13–C18) forms dihedral angles of 56.92 (12)° with the cyanobenzene ring (C22–C28/N1) and 40.91 (12) and 44.76 (12)°, respectively, with the fluorobenzene rings (C1–C6/F1 & C7–C12/F2). Bond lengths are angles are within the normal ranges and are comparable with the related structure (Fun, Chia et al., 2011).

In the crystal packing (Fig. 2), intermolecular C7—H7A···O1 and C29—H29A···F2 hydrogen bonds (Table 1) link the molecules to form planes parallel to the ab plane. The crystal packing is further stabilized by C—H···π interactions (Table 1), involving the central benzene ring.

Experimental

To a mixture of 1-(4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl) ethanone (0.338 g, 0.001 mol) and 4-cyanobenzaldehyde (0.131 g, 0.001 mol) in 30 ml e thanol, 0.5 ml of 10% sodium hydroxide solution was added and stirred at 5–10°C for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Colourless plates were grown from acetone solution by slow evaporation method and yield of the compound was 78%. M.p.: 450 K.