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

Richard Betz; Thomas Gerber; Eric Hosten; S Samshuddin; Badiadka Narayana; Hemmige S Yathirajan

doi:10.1107/S1600536811047696

. 2011 Nov 16;67(Pt 12):o3323–o3324. doi: 10.1107/S1600536811047696

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

Richard Betz ^a,^*, Thomas Gerber ^a, Eric Hosten ^a, S Samshuddin ^b, Badiadka Narayana ^b, Hemmige S Yathirajan ^c

PMCID: PMC3238973 PMID: 22199822

Abstract

The title compound, C₂₉H₂₂F₂O₃, is a meta-terphenyl derivative featuring a Michael-system-derived substituent with an E-configured C=C function. In the crystal, C—H⋯O and C—H⋯F contacts connect the molecules into planes parallel to (101). The shortest centroid–centroid distance between two aromatic systems is 3.7169 (7) Å and is apparent between the terminal benzene ring of the Michael-system-derived substituent and its symmetry-generated equivalent.

Related literature

For the pharmacological importance of terphenyls, see: Liu (2006 ▶) and of chalcones, see: Dhar (1981 ▶); Dimmock et al. (1999 ▶); Satyanarayana et al. (2004 ▶). For our work on the synthesis of different chalcone derivatives, see: Samshuddin et al. (2011 ▶); Fun et al. (2010 ▶); Jasinski et al. (2010 ▶); Baktır et al. (2011 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₉H₂₂F₂O₃
M _r = 456.47
Monoclinic,
a = 9.6059 (2) Å
b = 19.2236 (5) Å
c = 13.3772 (3) Å
β = 112.905 (1)°
V = 2275.46 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 200 K
0.54 × 0.51 × 0.51 mm

Data collection

Bruker APEXII CCD diffractometer
20209 measured reflections
5655 independent reflections
4754 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.125
S = 1.03
5655 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047696/qk2026sup1.cif

e-67-o3323-sup1.cif^{(36.1KB, cif)}

Supplementary material file. DOI: 10.1107/S1600536811047696/qk2026Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047696/qk2026Isup3.hkl

e-67-o3323-Isup3.hkl^{(276.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811047696/qk2026Isup4.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
C3—H3⋯F1ⁱ	0.95	2.51	3.4159 (15)	159
C5—H5B⋯O1ⁱⁱ	0.98	2.54	3.3534 (18)	141
C22—H22⋯O1ⁱⁱⁱ	0.95	2.51	3.4208 (18)	161

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

Acknowledgments

BN thanks the UGC for financial assistance under SAP and BSR one-time grants for the purchase of chemicals. SS thanks Mangalore University for research facilities.

supplementary crystallographic information

Comment

Chalcones constitute an important family of substances belonging to flavonoids, a large group of natural and synthetic products with interesting physicochemical properties, biological activity and structural characteristics. They have been reported to possess many interesting pharmacological activities (Dhar, 1981) including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999; Satyanarayana et al., 2004). In recent years, it has been reported that some terphenyls exhibit considerable biological activities (e.g. being potent anticoagulants, immunosuppressants, antithrombotics, neuroprotectives, specific 5-lipoxygenase inhibitors) and showing cytotoxic activities (Liu, 2006). In view of the pharmacological importance of terphenyls and chalcones, and in continuation of our work on synthesis of various derivatives of 4,4'-difluoro chalcone (Samshuddin et al., 2011, Fun et al., 2010, Jasinski et al., 2010, Baktır et al., 2011), the molecular and crystal structure of the title compound is reported.

The C=C function along the Michael system is (E)-configured. The least-squares planes defined by the respective carbon atoms of the individual para-fluorophenyl moieties enclose angles of 25.42 (5) ° and 64.01 (5) ° with the plane defined by the carbon atoms of the terphenyl's central phenyl ring.

In the crystal, C–H···O as well as C–H···F contacts can be observed whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the respective atoms. The C–H···O contacts stem from one of the hydrogen atoms of a para-fluoro phenyl moiety and one of the methoxy groups and invariably apply the ketonic oxygen atom as acceptor. The C–H···F contacts are exclusively supported by the vinylic hydrogen atom on the Michael system. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the C–H···F contacts is R²₂(26) on the unitary level while the C–H···O contacts necessitate a C¹₁(9)C¹₁(10) descriptor on the same level. In total, the molecules are connected to planes parallel (1 0 1). The shortest intercentroid distance between two ring centroids was found at 3.7169 (7) Å and is apparent between the methoxyphenyl moiety connected to the Michael system and its symmetry-generated equivalents. Details about metrical parameters of the C–H···O and C–H···F contacts as well as information about their symmetry can be found in Table 1 (Fig. 2).

Experimental

To a mixture of 1-(4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl) ethanone (3.38 g, 0.01 mol) and anisaldehyde (1.36 g, 0.01 mol) in 30 ml e thanol, 10 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 (yield: 79%). Single crystals suitable for the X-ray diffraction study were grown from DMF by slow evaporation at room temperature.