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

Hoong-Kun Fun; Tze Shyang Chia; S Samshuddin; B Narayana; B K Sarojini

doi:10.1107/S1600536812013852

. 2012 Apr 6;68(Pt 5):o1314–o1315. doi: 10.1107/S1600536812013852

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

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, S Samshuddin ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3344456 PMID: 22590218

Abstract

In the title compound, C₂₈H₁₉BrF₂O₂, the central benzene ring makes dihedral angles of 62.51 (18), 46.23 (18) and 48.19 (18)° with the bromo-substituted benzene ring and two terminal fluoro-substituted benzene rings, respectively. In the crystal, molecules are linked by C—H⋯F hydrogen bonds into infinite chains along [110]. Weak C—H⋯π and π–π interactions [centroid–centroid distance = 3.683 (2) Å] also occur and short intermolecular F⋯F contacts [2.833 (4) Å] are observed.

Related literature

For related structures and background to terphenyl chalcones, see: Fun et al. (2011a ▶,b ▶, 2012 ▶). For reference bond lengths, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₈H₁₉BrF₂O₂
M _r = 505.34
Monoclinic,
a = 22.4861 (6) Å
b = 6.9006 (2) Å
c = 28.6933 (8) Å
β = 101.286 (2)°
V = 4366.2 (2) Å³
Z = 8
Mo Kα radiation
μ = 1.92 mm⁻¹
T = 100 K
0.37 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.533, T _max = 0.863
24190 measured reflections
6414 independent reflections
4483 reflections with I > 2σ(I)
R _int = 0.076

Refinement

R[F ² > 2σ(F ²)] = 0.071
wR(F ²) = 0.134
S = 1.11
6414 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −1.09 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/S1600536812013852/hb6704sup1.cif

e-68-o1314-sup1.cif^{(30.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013852/hb6704Isup2.hkl

e-68-o1314-Isup2.hkl^{(314KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812013852/hb6704Isup3.cml

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

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

Cg1 and Cg2 are the centroids of C1—C6 and C10—C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28A⋯F2ⁱ	0.96	2.51	3.448 (4)	166
C4—H4A⋯Cg1ⁱⁱ	0.93	2.99	3.712 (5)	136
C20—H20A⋯Cg2ⁱⁱⁱ	0.93	2.72	3.383 (4)	129
C27—H27A⋯Cg1^iv	0.93	2.95	3.735 (4)	143
C28—H28B⋯Cg2^v	0.96	2.82	3.485 (4)	128

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

Acknowledgments

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

supplementary crystallographic information

Comment

In continuation of our work on the synthesis and structures of terphenyl chalcones (Fun et al., 2011a,b), the title compound (I) is now described. 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 (C10–C15) makes dihedral angles of 62.51 (18), 46.23 (18) and 48.19 (18)° with the bromo-substituted benzene ring (C1–C6) and two terminal fluoro-substituted benzene rings (C16–C21 & C22–C27), respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a,b, 2012).

In the crystal (Fig. 2), molecules are linked by C28—H28A···F2 hydrogen bonds into infinite chains along [110]. The crystal is further stabilized by C—H···π interactions (Table 1), involving Cg1 and Cg2 which are the centroids of C1—C6 and C10—C15 rings, respectively. π–π interaction is also observed with Cg4···Cg4 distance of 3.683 (2) Å [symmetry code: -1/2-X,3/2-Y,-Z], where Cg4 is the centroid of C22–C27 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 2-bromobenzaldehyde (0.185 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 needles were grown from DMF solution by slow evaporation method and yield of the compound was 79%. (m.p.: 440 K).