(2E)-1-(4,4′′-Difluoro-5′-meth­oxy-1,1′:3′,1′′-terphenyl-4′-yl)-3-[4-(methyl­sulfan­yl)phen­yl]prop-2-en-1-one

Rajni Kant; Vivek K Gupta; Kamini Kapoor; S Samshuddin; B Narayana

doi:10.1107/S1600536812030139

. 2012 Jul 7;68(Pt 8):o2378. doi: 10.1107/S1600536812030139

(2E)-1-(4,4′′-Difluoro-5′-methoxy-1,1′:3′,1′′-terphenyl-4′-yl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one

Rajni Kant ^a,^*, Vivek K Gupta ^a, Kamini Kapoor ^a, S Samshuddin ^b, B Narayana ^b

PMCID: PMC3414306 PMID: 22904839

Abstract

In the title compound, C₂₉H₂₂F₂O₂S, the central benzene ring makes dihedral angles of 45.83 (7), 38.90 (7) and 55.50 (7)° with the two fluoro-substituted benzene rings and the methylsulfanyl-substituted benzene ring, respectively. In the crystal, C—H⋯O contacts connect the molecules into layers lying perpendicular to the c axis. In addition, π–π stacking interactions between one of the fluorophenyl groups [centroid–centroid distances = 3.681 (1) and 3.818 (1) Å] are observed.

Related literature

For the pharmacological importance of terphenyls, see: Liu (2006 ▶); Gill & Steglich (1987 ▶). For related structures and background to terphenyl chalcones, see: Fun et al. (2011 ▶); Fun, Loh et al. (2012 ▶); Fun, Hemamalini et al. (2012 ▶); Samshuddin et al. (2012 ▶).

Experimental

Crystal data

C₂₉H₂₂F₂O₂S
M _r = 472.53
Triclinic,
a = 6.9341 (3) Å
b = 11.4440 (4) Å
c = 15.4719 (5) Å
α = 89.611 (3)°
β = 84.738 (3)°
γ = 74.981 (3)°
V = 1180.63 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.743, T _max = 1.000
17866 measured reflections
4637 independent reflections
2891 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.142
S = 1.06
4637 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030139/gk2507sup1.cif

e-68-o2378-sup1.cif^{(30KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030139/gk2507Isup2.hkl

e-68-o2378-Isup2.hkl^{(222.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812030139/gk2507Isup3.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.47	3.289 (3)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

RK acknowledges the Department of Science and Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003. BN thanks the UGC for financial assistance through BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

supplementary crystallographic information

Comment

The pharmacological importance of terphenyls is well documented (Gill & Steglich, 1987; Liu, 2006). The crystal structure of some terphenyl chalcones, viz. (E)-1-(4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl)-3-(6-methoxy naphthalen-2-yl)prop-2-en-1-one (Fun et al., 2011), (2E)-1- (4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl)-3-(2-fluorophenyl) prop-2-en-1-one (Fun, Hemamalini et al., 2012) and (E)-3-(2-chlorophenyl) -1-(4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl)prop-2-en-1-one (Samshuddin et al., 2012) have been reported. In view of the importance of terphenyls, the title compound (I) was prepared from 4,4'-difluoro chalcone by several steps (Fun, Loh et al., 2012) and its crystal structure is reported here.

All bond lengths and angles are normal and correspond to those observed in related structures. The central benzene ring forms dihedral angles of 45.83 (7), 38.90 (7) and 55.50 (7) ° with the two fluoro- substituted benzene rings and methylsulfanyl substituted benzene ring, respectively. In the crystal, molecules are connected via intermolecular C—H···O hydrogen bonds (Fig.2) to form layers. The crystal structure is further stabilized by π-π interactions between the benzene ring (C10—C15) of the molecule at (x, y, z) and the same benzene ring of inversion related molecules at (2 - x, -1 - y, -z) [centroid separation = 3.681 (1) Å, interplanar spacing = 3.512 Å and centroid shift = 1.102 Å] and (1 - x, -1 - y, -z) [centroid separation = 3.818 (1) Å, interplanar spacing = 3.379 Å and centroid shift = 1.777 Å].

Experimental

To a mixture of 1-(4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl)ethanone (0.338 g, 001 mol) and 4-(methylsulfanyl)benzaldehyde (0.152 g, 0.001 mol) in 30 ml ethanol, 0.5 ml of 10% sodium hydroxide solution was added and the reaction mixture was stirred at 5–10°C for 3 hrs. The precipitate formed was collected by filtration and purified by recrystallization from ethanol ( yield 72%; m.p. 407 K). Single-crystal was grown from DMF by slow evaporation method.