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

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

doi:10.1107/S1600536812024981

. 2012 Jun 13;68(Pt 7):o2024. doi: 10.1107/S1600536812024981

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

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

PMCID: PMC3393293 PMID: 22807850

Abstract

In the title compound, C₂₈H₁₉F₃O₂, the central benzene ring forms dihedral angles of 48.69 (6), 60.93 (6) and 42.06 (6)° with the fluorobenzene rings. In the crystal, intermolecular C—H⋯O and C—H⋯F hydrogen bonds link the molecules, forming an undulating two-dimensional network parallel to the bc plane. C—H⋯π interactions further consolidate the crystal packing.

Related literature

For background to terphenyl chalcones, see: Fun et al. (2011 ▶); Fun, Hemamalini et al. (2012 ▶). For a related structure, see: Fun, Loh et al. (2012 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₈H₁₉F₃O₂
M _r = 444.43
Monoclinic,
a = 13.7592 (1) Å
b = 6.7898 (1) Å
c = 22.4361 (3) Å
β = 101.908 (1)°
V = 2050.92 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.32 × 0.24 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.966, T _max = 0.987
28707 measured reflections
7478 independent reflections
5317 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.140
S = 1.03
7478 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.26 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/S1600536812024981/is5146sup1.cif

e-68-o2024-sup1.cif^{(30.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024981/is5146Isup2.hkl

e-68-o2024-Isup2.hkl^{(365.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812024981/is5146Isup3.cml

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

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

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O2ⁱ	0.95	2.40	3.3008 (18)	158
C19—H19A⋯F2ⁱⁱ	0.95	2.54	3.2326 (18)	130
C24—H24A⋯Cg1ⁱⁱⁱ	0.95	2.84	3.4579 (15)	124
C28—H28C⋯Cg1^iv	0.98	2.86	3.5461 (16)	128

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

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 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, Hemamalini et al., 2012).

In the title compound (Fig. 1), the central benzene ring (C7–C12) forms dihedral angles of 48.69 (6), 60.93 (6) and 42.06 (6)°, respectively, with the fluorobenzene rings C1–C6/F1, C16–C21/F3 and C22–C27/F2. Bond lengths and angles are within the normal ranges and are comparable with the related structure (Fun, Loh et al., 2012).

In the crystal packing (Fig. 2), intermolecular C4—H4A···O2 and C19—H19A···F2 hydrogen bonds (Table 1) link the molecules to form undulating two-dimensional network parallel to the bc plane. C—H···π interactions (Table 1), involving the central benzene ring, further consolidate the crystal packing.

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 2-fluorobenzaldehyde (0.124 g, 0.001 mol) in 30 ml ethanol, 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. The single-crystal was grown from methanol by slow evaporation method and yield of the compound was 74%. M.p.: 453 K.