organic compounds
1-(4,4′′-Difluoro-5′-methoxy-1,1′:3′,1′′-terphenyl-4′-yl)ethanone
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
*Correspondence e-mail: hkfun@usm.my
In the title compound, C21H16F2O2, the central benzene ring is inclined at dihedral angles of 30.91 (8) and 46.88 (7)° to the two terminal fluoro-substituted rings. The dihedral angle between the two terminal fluoro-subsituted rings is 68.34 (8)°. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The is stabilized by weak C—H⋯π interactions.
Related literature
For a related structure and background to terphenyls, see: Fun, Chia et al. (2011); Samshuddin et al. (2011). For chalcone derivatives of the title compound, see: Fun, Hemamalini et al. (2011); Betz et al. (2011a,b). For the synthetic procedure, see: Kotnis (1990). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell 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).
Supporting information
10.1107/S1600536811053037/rz2681sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811053037/rz2681Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811053037/rz2681Isup3.cml
The title compound was prepared by the aromatization of the cyclohexenone derivative, (6Z)-3,5-bis(4-fluorophenyl)-6-(1-hydroxyethylidene)cyclo hex-2-en-1-one, using iodine and methanol at reflux condition (Kotnis, 1990). Single crystal of the product was grown from a mixture of ethanol and DMF (1:1 v/v) by slow evaporation method (m.p. 391K).
All hydrogen atoms were positioned geometrically [C–H = 0.93 or 0.96 Å] and were refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C21H16F2O2 | F(000) = 704 |
Mr = 338.34 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3484 reflections |
a = 6.0816 (7) Å | θ = 2.5–24.5° |
b = 25.997 (3) Å | µ = 0.10 mm−1 |
c = 10.9061 (12) Å | T = 296 K |
β = 100.866 (2)° | Plate, colourless |
V = 1693.4 (3) Å3 | 0.74 × 0.31 × 0.10 mm |
Z = 4 |
Bruker APEXII DUO CCD area-detector diffractometer | 4923 independent reflections |
Radiation source: fine-focus sealed tube | 2883 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ϕ and ω scans | θmax = 30.1°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −8→8 |
Tmin = 0.930, Tmax = 0.990 | k = −33→36 |
17519 measured reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0857P)2 + 0.0565P] where P = (Fo2 + 2Fc2)/3 |
4923 reflections | (Δ/σ)max = 0.001 |
228 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C21H16F2O2 | V = 1693.4 (3) Å3 |
Mr = 338.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.0816 (7) Å | µ = 0.10 mm−1 |
b = 25.997 (3) Å | T = 296 K |
c = 10.9061 (12) Å | 0.74 × 0.31 × 0.10 mm |
β = 100.866 (2)° |
Bruker APEXII DUO CCD area-detector diffractometer | 4923 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2883 reflections with I > 2σ(I) |
Tmin = 0.930, Tmax = 0.990 | Rint = 0.033 |
17519 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.23 e Å−3 |
4923 reflections | Δρmin = −0.27 e Å−3 |
228 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.7590 (3) | 0.93216 (6) | 0.59950 (13) | 0.1136 (5) | |
F2 | −0.8096 (2) | 1.00075 (4) | −0.25890 (13) | 0.0932 (4) | |
O1 | 0.0345 (2) | 0.73907 (4) | 0.00260 (11) | 0.0617 (3) | |
O2 | −0.4540 (2) | 0.77193 (5) | −0.13608 (13) | 0.0825 (4) | |
C1 | 0.2502 (3) | 0.91677 (6) | 0.37217 (14) | 0.0527 (4) | |
H1A | 0.1061 | 0.9302 | 0.3545 | 0.063* | |
C2 | 0.3999 (3) | 0.93447 (7) | 0.47550 (16) | 0.0647 (5) | |
H2A | 0.3569 | 0.9592 | 0.5279 | 0.078* | |
C3 | 0.6109 (4) | 0.91488 (7) | 0.49859 (17) | 0.0705 (5) | |
C4 | 0.6816 (3) | 0.87831 (8) | 0.42537 (18) | 0.0711 (5) | |
H4A | 0.8267 | 0.8655 | 0.4444 | 0.085* | |
C5 | 0.5325 (3) | 0.86066 (6) | 0.32199 (15) | 0.0586 (4) | |
H5A | 0.5795 | 0.8362 | 0.2703 | 0.070* | |
C6 | 0.3128 (3) | 0.87898 (5) | 0.29407 (13) | 0.0456 (3) | |
C7 | 0.1516 (2) | 0.85840 (5) | 0.18611 (13) | 0.0457 (3) | |
C8 | 0.1709 (3) | 0.80732 (6) | 0.14915 (13) | 0.0502 (4) | |
H8A | 0.2819 | 0.7863 | 0.1935 | 0.060* | |
C9 | 0.0255 (3) | 0.78806 (5) | 0.04698 (14) | 0.0493 (3) | |
C10 | −0.1469 (3) | 0.81858 (5) | −0.01979 (13) | 0.0467 (3) | |
C11 | −0.1702 (2) | 0.86946 (5) | 0.01721 (13) | 0.0455 (3) | |
C12 | −0.0200 (2) | 0.88852 (5) | 0.12041 (13) | 0.0465 (3) | |
H12A | −0.0354 | 0.9223 | 0.1457 | 0.056* | |
C13 | −0.3440 (2) | 0.90439 (5) | −0.05353 (12) | 0.0454 (3) | |
C14 | −0.5668 (3) | 0.88925 (6) | −0.08926 (16) | 0.0573 (4) | |
H14A | −0.6106 | 0.8570 | −0.0661 | 0.069* | |
C15 | −0.7240 (3) | 0.92160 (7) | −0.15882 (17) | 0.0660 (5) | |
H15A | −0.8721 | 0.9112 | −0.1837 | 0.079* | |
C16 | −0.6553 (3) | 0.96922 (7) | −0.18989 (15) | 0.0612 (4) | |
C17 | −0.4413 (3) | 0.98642 (6) | −0.15416 (16) | 0.0610 (4) | |
H17A | −0.4010 | 1.0194 | −0.1748 | 0.073* | |
C18 | −0.2853 (3) | 0.95354 (6) | −0.08626 (14) | 0.0525 (4) | |
H18A | −0.1380 | 0.9645 | −0.0619 | 0.063* | |
C19 | 0.2322 (3) | 0.70987 (6) | 0.04690 (18) | 0.0668 (5) | |
H19A | 0.2267 | 0.6783 | 0.0007 | 0.100* | |
H19B | 0.2417 | 0.7023 | 0.1339 | 0.100* | |
H19C | 0.3612 | 0.7293 | 0.0359 | 0.100* | |
C20 | −0.2837 (3) | 0.79540 (6) | −0.13640 (15) | 0.0548 (4) | |
C21 | −0.1930 (4) | 0.80270 (11) | −0.25154 (18) | 0.0997 (8) | |
H21A | −0.2653 | 0.7793 | −0.3146 | 0.150* | |
H21B | −0.0348 | 0.7961 | −0.2344 | 0.150* | |
H21C | −0.2198 | 0.8374 | −0.2805 | 0.150* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.1147 (10) | 0.1119 (10) | 0.0921 (9) | −0.0152 (8) | −0.0369 (8) | −0.0252 (8) |
F2 | 0.0933 (8) | 0.0800 (8) | 0.0952 (9) | 0.0405 (6) | −0.0111 (7) | 0.0045 (6) |
O1 | 0.0756 (8) | 0.0373 (6) | 0.0671 (7) | 0.0058 (5) | 0.0004 (6) | −0.0108 (5) |
O2 | 0.0853 (9) | 0.0775 (9) | 0.0815 (9) | −0.0340 (7) | 0.0074 (7) | −0.0082 (7) |
C1 | 0.0663 (9) | 0.0407 (8) | 0.0495 (8) | −0.0009 (7) | 0.0069 (7) | 0.0013 (6) |
C2 | 0.0898 (13) | 0.0491 (9) | 0.0520 (9) | −0.0063 (9) | 0.0056 (9) | −0.0073 (7) |
C3 | 0.0818 (12) | 0.0611 (11) | 0.0591 (10) | −0.0144 (9) | −0.0106 (9) | −0.0027 (8) |
C4 | 0.0575 (10) | 0.0697 (12) | 0.0788 (12) | −0.0044 (8) | −0.0055 (9) | 0.0030 (10) |
C5 | 0.0603 (9) | 0.0524 (9) | 0.0618 (9) | −0.0009 (7) | 0.0084 (8) | −0.0030 (7) |
C6 | 0.0576 (8) | 0.0351 (7) | 0.0433 (7) | −0.0028 (6) | 0.0072 (6) | 0.0044 (5) |
C7 | 0.0572 (8) | 0.0358 (7) | 0.0439 (7) | −0.0007 (6) | 0.0092 (6) | 0.0012 (5) |
C8 | 0.0618 (9) | 0.0367 (7) | 0.0497 (8) | 0.0041 (6) | 0.0046 (7) | 0.0008 (6) |
C9 | 0.0628 (9) | 0.0340 (7) | 0.0509 (8) | −0.0001 (6) | 0.0101 (7) | −0.0020 (6) |
C10 | 0.0559 (8) | 0.0383 (7) | 0.0458 (7) | −0.0034 (6) | 0.0096 (6) | −0.0011 (6) |
C11 | 0.0513 (8) | 0.0387 (7) | 0.0465 (7) | −0.0005 (6) | 0.0095 (6) | 0.0010 (6) |
C12 | 0.0578 (8) | 0.0349 (7) | 0.0461 (7) | 0.0025 (6) | 0.0079 (6) | −0.0026 (5) |
C13 | 0.0528 (8) | 0.0404 (7) | 0.0440 (7) | 0.0030 (6) | 0.0118 (6) | −0.0010 (6) |
C14 | 0.0554 (9) | 0.0489 (9) | 0.0683 (10) | −0.0005 (7) | 0.0137 (8) | 0.0020 (7) |
C15 | 0.0510 (9) | 0.0665 (12) | 0.0785 (11) | 0.0080 (8) | 0.0067 (8) | −0.0084 (9) |
C16 | 0.0680 (10) | 0.0585 (10) | 0.0543 (9) | 0.0224 (8) | 0.0044 (8) | −0.0016 (8) |
C17 | 0.0752 (11) | 0.0441 (9) | 0.0651 (10) | 0.0090 (8) | 0.0171 (9) | 0.0089 (7) |
C18 | 0.0545 (8) | 0.0444 (8) | 0.0586 (9) | 0.0012 (6) | 0.0106 (7) | 0.0015 (7) |
C19 | 0.0764 (11) | 0.0456 (9) | 0.0781 (12) | 0.0123 (8) | 0.0141 (9) | −0.0103 (8) |
C20 | 0.0607 (9) | 0.0445 (8) | 0.0571 (9) | −0.0012 (7) | 0.0057 (7) | −0.0054 (7) |
C21 | 0.0960 (16) | 0.145 (2) | 0.0591 (11) | −0.0280 (15) | 0.0183 (11) | −0.0237 (13) |
F1—C3 | 1.360 (2) | C10—C20 | 1.508 (2) |
F2—C16 | 1.3610 (19) | C11—C12 | 1.3997 (19) |
O1—C9 | 1.3671 (17) | C11—C13 | 1.4930 (19) |
O1—C19 | 1.427 (2) | C12—H12A | 0.9300 |
O2—C20 | 1.203 (2) | C13—C18 | 1.391 (2) |
C1—C2 | 1.387 (2) | C13—C14 | 1.394 (2) |
C1—C6 | 1.399 (2) | C14—C15 | 1.387 (2) |
C1—H1A | 0.9300 | C14—H14A | 0.9300 |
C2—C3 | 1.359 (3) | C15—C16 | 1.369 (3) |
C2—H2A | 0.9300 | C15—H15A | 0.9300 |
C3—C4 | 1.362 (3) | C16—C17 | 1.362 (3) |
C4—C5 | 1.385 (2) | C17—C18 | 1.383 (2) |
C4—H4A | 0.9300 | C17—H17A | 0.9300 |
C5—C6 | 1.397 (2) | C18—H18A | 0.9300 |
C5—H5A | 0.9300 | C19—H19A | 0.9600 |
C6—C7 | 1.483 (2) | C19—H19B | 0.9600 |
C7—C12 | 1.3904 (19) | C19—H19C | 0.9600 |
C7—C8 | 1.399 (2) | C20—C21 | 1.476 (3) |
C8—C9 | 1.379 (2) | C21—H21A | 0.9600 |
C8—H8A | 0.9300 | C21—H21B | 0.9600 |
C9—C10 | 1.404 (2) | C21—H21C | 0.9600 |
C10—C11 | 1.398 (2) | ||
C9—O1—C19 | 117.60 (12) | C7—C12—H12A | 119.1 |
C2—C1—C6 | 121.04 (16) | C11—C12—H12A | 119.1 |
C2—C1—H1A | 119.5 | C18—C13—C14 | 118.05 (14) |
C6—C1—H1A | 119.5 | C18—C13—C11 | 120.02 (13) |
C3—C2—C1 | 118.57 (17) | C14—C13—C11 | 121.93 (13) |
C3—C2—H2A | 120.7 | C15—C14—C13 | 121.03 (16) |
C1—C2—H2A | 120.7 | C15—C14—H14A | 119.5 |
C2—C3—F1 | 118.96 (19) | C13—C14—H14A | 119.5 |
C2—C3—C4 | 122.96 (16) | C16—C15—C14 | 118.18 (16) |
F1—C3—C4 | 118.09 (19) | C16—C15—H15A | 120.9 |
C3—C4—C5 | 118.56 (18) | C14—C15—H15A | 120.9 |
C3—C4—H4A | 120.7 | F2—C16—C17 | 118.85 (16) |
C5—C4—H4A | 120.7 | F2—C16—C15 | 118.08 (17) |
C4—C5—C6 | 121.13 (16) | C17—C16—C15 | 123.08 (15) |
C4—C5—H5A | 119.4 | C16—C17—C18 | 118.17 (16) |
C6—C5—H5A | 119.4 | C16—C17—H17A | 120.9 |
C5—C6—C1 | 117.73 (14) | C18—C17—H17A | 120.9 |
C5—C6—C7 | 120.81 (13) | C17—C18—C13 | 121.45 (15) |
C1—C6—C7 | 121.46 (14) | C17—C18—H18A | 119.3 |
C12—C7—C8 | 118.78 (13) | C13—C18—H18A | 119.3 |
C12—C7—C6 | 121.72 (12) | O1—C19—H19A | 109.5 |
C8—C7—C6 | 119.49 (13) | O1—C19—H19B | 109.5 |
C9—C8—C7 | 120.08 (14) | H19A—C19—H19B | 109.5 |
C9—C8—H8A | 120.0 | O1—C19—H19C | 109.5 |
C7—C8—H8A | 120.0 | H19A—C19—H19C | 109.5 |
O1—C9—C8 | 124.16 (14) | H19B—C19—H19C | 109.5 |
O1—C9—C10 | 114.76 (13) | O2—C20—C21 | 121.87 (16) |
C8—C9—C10 | 121.08 (13) | O2—C20—C10 | 122.61 (15) |
C11—C10—C9 | 119.45 (13) | C21—C20—C10 | 115.52 (15) |
C11—C10—C20 | 123.47 (13) | C20—C21—H21A | 109.5 |
C9—C10—C20 | 116.81 (12) | C20—C21—H21B | 109.5 |
C10—C11—C12 | 118.71 (13) | H21A—C21—H21B | 109.5 |
C10—C11—C13 | 121.79 (13) | C20—C21—H21C | 109.5 |
C12—C11—C13 | 119.44 (12) | H21A—C21—H21C | 109.5 |
C7—C12—C11 | 121.86 (13) | H21B—C21—H21C | 109.5 |
C6—C1—C2—C3 | 1.0 (3) | C20—C10—C11—C12 | −173.84 (14) |
C1—C2—C3—F1 | 179.78 (16) | C9—C10—C11—C13 | 177.29 (14) |
C1—C2—C3—C4 | −0.5 (3) | C20—C10—C11—C13 | 3.5 (2) |
C2—C3—C4—C5 | 0.7 (3) | C8—C7—C12—C11 | −1.3 (2) |
F1—C3—C4—C5 | −179.64 (17) | C6—C7—C12—C11 | 178.96 (14) |
C3—C4—C5—C6 | −1.3 (3) | C10—C11—C12—C7 | 0.4 (2) |
C4—C5—C6—C1 | 1.7 (2) | C13—C11—C12—C7 | −176.95 (13) |
C4—C5—C6—C7 | −177.57 (15) | C10—C11—C13—C18 | −131.38 (16) |
C2—C1—C6—C5 | −1.6 (2) | C12—C11—C13—C18 | 45.89 (19) |
C2—C1—C6—C7 | 177.70 (14) | C10—C11—C13—C14 | 48.3 (2) |
C5—C6—C7—C12 | −149.43 (15) | C12—C11—C13—C14 | −134.44 (16) |
C1—C6—C7—C12 | 31.3 (2) | C18—C13—C14—C15 | 2.0 (2) |
C5—C6—C7—C8 | 30.9 (2) | C11—C13—C14—C15 | −177.66 (14) |
C1—C6—C7—C8 | −148.36 (15) | C13—C14—C15—C16 | −1.0 (3) |
C12—C7—C8—C9 | 1.9 (2) | C14—C15—C16—F2 | 179.55 (15) |
C6—C7—C8—C9 | −178.40 (14) | C14—C15—C16—C17 | −1.0 (3) |
C19—O1—C9—C8 | −14.0 (2) | F2—C16—C17—C18 | −178.69 (14) |
C19—O1—C9—C10 | 166.16 (14) | C15—C16—C17—C18 | 1.8 (3) |
C7—C8—C9—O1 | 178.61 (14) | C16—C17—C18—C13 | −0.7 (2) |
C7—C8—C9—C10 | −1.5 (2) | C14—C13—C18—C17 | −1.1 (2) |
O1—C9—C10—C11 | −179.55 (13) | C11—C13—C18—C17 | 178.55 (14) |
C8—C9—C10—C11 | 0.6 (2) | C11—C10—C20—O2 | −93.9 (2) |
O1—C9—C10—C20 | −5.3 (2) | C9—C10—C20—O2 | 92.1 (2) |
C8—C9—C10—C20 | 174.82 (15) | C11—C10—C20—C21 | 87.0 (2) |
C9—C10—C11—C12 | 0.0 (2) | C9—C10—C20—C21 | −87.0 (2) |
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···O2 | 0.93 | 2.58 | 3.188 (2) | 124 |
C19—H19A···Cg1i | 0.96 | 2.80 | 3.6432 (19) | 147 |
Symmetry code: (i) x, −y+1/2, z−3/2. |
Experimental details
Crystal data | |
Chemical formula | C21H16F2O2 |
Mr | 338.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 6.0816 (7), 25.997 (3), 10.9061 (12) |
β (°) | 100.866 (2) |
V (Å3) | 1693.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.74 × 0.31 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.930, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17519, 4923, 2883 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.167, 1.03 |
No. of reflections | 4923 |
No. of parameters | 228 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.27 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···O2 | 0.9300 | 2.5800 | 3.188 (2) | 124.00 |
C19—H19A···Cg1i | 0.9600 | 2.8000 | 3.6432 (19) | 147.00 |
Symmetry code: (i) x, −y+1/2, z−3/2. |
Footnotes
‡Thomson Reuters ResearcherID: A-3561-2009.
Acknowledgements
HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral 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 research facilities.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As a part of our ongoing studies on synthesis of terphenyl moiety from 4,4'-difluoro chalcone (Fun, Chia et al., 2011; Samshuddin et al., 2011), the title compound was prepared and its crystal structure is reported. We have used this acetyl terphenyl as a starting material for many chalcones (Fun, Hemamalini et al., 2011; Betz et al., 2011a,b).
The asymmetric unit of the title compound is shown in Fig. 1. The central benzene (C7–C12) ring is inclined at dihedral angles of 30.91 (8) and 46.88 (7)° to the two terminal fluoro-substituted phenyl (C1–C6, C13–C18) rings, respectively. The corresponding angle between the two terminal fluoro-subsituted phenyl rings is 68.34 (8)°.
An intramolecular C—H···O hydrogen bond generates an S(6) (Bernstein et al., 1995) ring motif in the molecule (Fig. 1; Table 1). The crystal structure (Fig. 2) is stabilized by weak C—H···π interactions (Table 1) involving the C1–C6 ring (centroid Cg1).