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

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

doi:10.1107/S1600536812017692

. 2012 Apr 28;68(Pt 5):o1538–o1539. doi: 10.1107/S1600536812017692

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

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

PMCID: PMC3344640 PMID: 22590402

Abstract

The title compound, C₂₈H₁₉ClF₂O₂, is a polysubstituted terphenyl derivative bearing a Michael system in which the C=C double bond has an E conformation. In the crystal, C—H⋯Cl and C—H⋯O contacts connect the molecules into layers lying perpendicular to the a axis. The shortest intercentroid distance between symmetry-related 4-fluorophenyl groups is 3.7547 (16) Å.

Related literature

For pharmacological background information about terphenyls, see: Astrue (2002 ▶); Liu (2006 ▶). For the crystal structures of other terphenyl derivatives, see: Betz et al. (2011a ▶,b ▶,c ▶,d ▶,e ▶); Samshuddin et al. (2011 ▶). For graph-set analysis, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₈H₁₉ClF₂O₂
M _r = 460.88
Monoclinic,
a = 14.2065 (7) Å
b = 6.8651 (3) Å
c = 22.4817 (11) Å
β = 101.406 (2)°
V = 2149.32 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 200 K
0.40 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.918, T _max = 0.962
17828 measured reflections
5318 independent reflections
3817 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.141
S = 1.07
5318 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.31 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/S1600536812017692/su2410sup1.cif

e-68-o1538-sup1.cif^{(28.7KB, cif)}

Supplementary material file. DOI: 10.1107/S1600536812017692/su2410Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017692/su2410Isup3.hkl

e-68-o1538-Isup3.hkl^{(260.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812017692/su2410Isup4.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
C23—H23⋯Cl1ⁱ	0.95	2.73	3.641 (2)	161
C33—H33⋯Cl1ⁱⁱ	0.95	2.76	3.697 (3)	170
C43—H43⋯O1ⁱ	0.95	2.54	3.411 (3)	153

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

Acknowledgments

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

supplementary crystallographic information

Comment

Polysubstituted aromatics are key structures of great efficacy in synthetic, medicinal and natural product chemistry. Terphenyl derivatives exhibit a considerable range of biological activities and show anticoagulant, immunosuppressant, antithrombotic, neuroprotective, specific 5-lipoxygenase inhibitory and cytotoxic activity effects (Liu, 2006). Due to their promising biological activities terphenyls have received increasing research interest. Therefore, synthesis of polysubstituted aromatics has been a fascinating area in the field of organic chemistry (Astrue, 2002). The molecular and crystal structures of several terphenyl derivatives (Samshuddin et al., 2011; Betz et al., 2011a,b,c,d,e) have already been reported. In view of the importance of these derivatives, the title compound was prepared and its molecular and crystal structure is reported.

The C═C double of the Michael system has an E conformation. The mean planes of the para-fluoro phenyl rings, (C31-C36) and (C41-C46), of the terphenyl moiety and the central phenyl ring (C21-C26), enclose angles of 43.39 (12)° and 49.65 (13)°, respectively (Fig. 1).

In the crystal, two different C–H···Cl contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating are observed (Fig. 2 and Table 1). These are supported by two different hydrogen atoms of the terphenyl moiety. Apart from these, a C–H···O contact involving a hydrogen atom from one of the para-fluoro phenyl ring (C41-C46) and the ketonic oxygen atom O1 is apparent (Fig. 2 and Table 1). In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the C–H···F contacts is C¹₁(10)C¹₁(12) on the unary level while the C–H···O contacts necessitate a C¹₁(10) descriptor on the same level. In total, the molecules are connected to form layers lying perpendicular to the a axis (Fig. 3).

The shortest intercentroid distance between two π systems was found at 3.7547 (16) Å and is apparent between the para-fluoro phenyl ring (C41-C46) and its symmetry-generated (-x, y-1/2, -z-1/2) equivalent.

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-chlorobenzaldehyde (0.104 g, 0.001 mol) in 30 ml of ethanol, 1 ml of a 10% sodium hydroxide solution was added and stirred at 278–283 K for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from DMF by slow evaporation at room temperature. The yield of the title compound was 81% (m.p.: 452 K).