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Acta Crystallogr Sect E Struct Rep Online. 2012 July 1; 68(Pt 7): o2024.
Published online 2012 June 13. doi:  10.1107/S1600536812024981
PMCID: PMC3393293

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

Abstract

In the title compound, C28H19F3O2, the central benzene ring forms dihedral angles of 48.69 (6), 60.93 (6) and 42.06 (6)° with the fluoro­benzene rings. In the crystal, inter­molecular C—H(...)O and C—H(...)F hydrogen bonds link the mol­ecules, forming an undulating two-dimensional network parallel to the bc plane. C—H(...)π inter­actions further consolidate the crystal packing.

Related literature  

For background to terphenyl chalcones, see: Fun et al. (2011 [triangle]); Fun, Hemamalini et al. (2012 [triangle]). For a related structure, see: Fun, Loh et al. (2012 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-o2024-scheme1.jpg

Experimental  

Crystal data  

  • C28H19F3O2
  • M r = 444.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o2024-efi1.jpg
  • a = 13.7592 (1) Å
  • b = 6.7898 (1) Å
  • c = 22.4361 (3) Å
  • β = 101.908 (1)°
  • V = 2050.92 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 100 K
  • 0.32 × 0.24 × 0.12 mm

Data collection  

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.966, T max = 0.987
  • 28707 measured reflections
  • 7478 independent reflections
  • 5317 reflections with I > 2σ(I)
  • R int = 0.041

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.140
  • S = 1.03
  • 7478 reflections
  • 299 parameters
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812024981/is5146sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024981/is5146Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024981/is5146Isup3.cml

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

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). 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 synthesis of terphenyl chalcones (Fun et al., 2011), the title compound is prepared and its crystal structure is reported. The starting material of the title compound was prepared from 4,4'-difluoro chalcone by several steps (Fun, Hemamalini et al., 2012).

In the title compound (Fig. 1), the central benzene ring (C7–C12) forms dihedral angles of 48.69 (6), 60.93 (6) and 42.06 (6)°, respectively, with the fluorobenzene rings C1–C6/F1, C16–C21/F3 and C22–C27/F2. Bond lengths and angles are within the normal ranges and are comparable with the related structure (Fun, Loh et al., 2012).

In the crystal packing (Fig. 2), intermolecular C4—H4A···O2 and C19—H19A···F2 hydrogen bonds (Table 1) link the molecules to form undulating two-dimensional network parallel to the bc plane. C—H···π interactions (Table 1), involving the central benzene ring, further consolidate the crystal packing.

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-fluorobenzaldehyde (0.124 g, 0.001 mol) in 30 ml ethanol, 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. The single-crystal was grown from methanol by slow evaporation method and yield of the compound was 74%. M.p.: 453 K.

Refinement

All the H atoms were positioned geometrically and were refined with a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C) (C—H = 0.95 or 0.98 Å). A rotating group model was applied to the methyl group. In the final refinement, one outliner (-13 1 30) was omitted.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
Fig. 2.
The crystal packing of the title compound, viewed along the c axis, showing the undulating two-dimensional network parallel to the bc plane. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C28H19F3O2F(000) = 920
Mr = 444.43Dx = 1.439 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6446 reflections
a = 13.7592 (1) Åθ = 3.1–32.6°
b = 6.7898 (1) ŵ = 0.11 mm1
c = 22.4361 (3) ÅT = 100 K
β = 101.908 (1)°Block, yellow
V = 2050.92 (4) Å30.32 × 0.24 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer7478 independent reflections
Radiation source: fine-focus sealed tube5317 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
[var phi] and ω scansθmax = 32.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −20→20
Tmin = 0.966, Tmax = 0.987k = −10→10
28707 measured reflectionsl = −34→31

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0578P)2 + 0.9821P] where P = (Fo2 + 2Fc2)/3
7478 reflections(Δ/σ)max = 0.001
299 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
F11.03222 (7)0.04726 (14)1.35190 (4)0.0244 (2)
F20.49534 (7)0.88570 (14)0.94449 (4)0.0250 (2)
F30.66995 (7)0.00341 (15)0.68457 (4)0.0257 (2)
O10.88761 (8)−0.12968 (16)0.95428 (5)0.0185 (2)
O20.77791 (8)0.32186 (16)0.88556 (5)0.0206 (2)
C11.01130 (10)0.0527 (2)1.18851 (7)0.0159 (3)
H1A1.05290.04731.15960.019*
C21.05342 (11)0.0473 (2)1.25032 (7)0.0173 (3)
H2A1.12340.04071.26420.021*
C30.99095 (11)0.0519 (2)1.29097 (6)0.0169 (3)
C40.88906 (11)0.0613 (2)1.27336 (7)0.0183 (3)
H4A0.84810.06131.30260.022*
C50.84821 (10)0.0706 (2)1.21143 (7)0.0167 (3)
H5A0.77820.08041.19820.020*
C60.90827 (10)0.0659 (2)1.16825 (6)0.0138 (3)
C70.86489 (10)0.0826 (2)1.10200 (6)0.0134 (2)
C80.79555 (9)0.2298 (2)1.08064 (6)0.0131 (2)
H8A0.77200.31111.10910.016*
C90.76002 (9)0.2601 (2)1.01833 (6)0.0124 (2)
C100.79304 (9)0.1352 (2)0.97656 (6)0.0125 (2)
C110.85927 (9)−0.0180 (2)0.99851 (6)0.0131 (2)
C120.89648 (10)−0.0432 (2)1.06048 (6)0.0141 (3)
H12A0.9430−0.14501.07450.017*
C130.76484 (9)0.1637 (2)0.90865 (6)0.0140 (3)
C140.72077 (10)−0.0086 (2)0.87229 (6)0.0167 (3)
H14A0.7023−0.12010.89300.020*
C150.70598 (10)−0.0131 (2)0.81141 (7)0.0164 (3)
H15A0.72470.09980.79140.020*
C160.66305 (10)−0.1795 (2)0.77340 (6)0.0157 (3)
C170.64452 (10)−0.1661 (2)0.71015 (7)0.0174 (3)
C180.60072 (11)−0.3144 (2)0.67147 (7)0.0206 (3)
H18A0.5895−0.29830.62850.025*
C190.57362 (11)−0.4870 (2)0.69676 (7)0.0212 (3)
H19A0.5423−0.58990.67110.025*
C200.59242 (11)−0.5092 (2)0.75979 (7)0.0211 (3)
H20A0.5748−0.62810.77720.025*
C210.63683 (11)−0.3579 (2)0.79707 (7)0.0188 (3)
H21A0.6499−0.37580.84000.023*
C220.68836 (9)0.4236 (2)0.99834 (6)0.0125 (2)
C230.70360 (10)0.6066 (2)1.02758 (6)0.0147 (3)
H23A0.75920.62391.06020.018*
C240.63912 (10)0.7636 (2)1.00989 (7)0.0160 (3)
H24A0.65030.88791.02960.019*
C250.55861 (10)0.7334 (2)0.96299 (7)0.0167 (3)
C260.53926 (10)0.5546 (2)0.93351 (6)0.0163 (3)
H26A0.48270.53810.90160.020*
C270.60454 (10)0.3997 (2)0.95175 (6)0.0142 (3)
H27A0.59200.27550.93220.017*
C280.93885 (11)−0.3103 (2)0.97216 (7)0.0192 (3)
H28A0.9470−0.38320.93580.029*
H28B0.9004−0.38990.99550.029*
H28C1.0043−0.28170.99750.029*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0348 (5)0.0252 (5)0.0101 (4)0.0019 (4)−0.0027 (4)0.0002 (3)
F20.0312 (5)0.0224 (5)0.0208 (5)0.0136 (4)0.0040 (4)0.0047 (4)
F30.0358 (5)0.0264 (5)0.0141 (4)−0.0069 (4)0.0035 (4)0.0046 (4)
O10.0242 (5)0.0179 (5)0.0140 (5)0.0080 (4)0.0051 (4)−0.0017 (4)
O20.0292 (5)0.0179 (5)0.0163 (5)−0.0003 (4)0.0084 (4)0.0024 (4)
C10.0160 (6)0.0160 (6)0.0153 (7)0.0009 (5)0.0023 (5)0.0005 (5)
C20.0176 (6)0.0156 (6)0.0163 (7)0.0012 (5)−0.0018 (5)−0.0002 (5)
C30.0255 (7)0.0136 (6)0.0097 (6)0.0000 (5)−0.0006 (5)0.0004 (5)
C40.0237 (7)0.0185 (7)0.0139 (7)0.0007 (5)0.0066 (5)0.0000 (5)
C50.0163 (6)0.0182 (6)0.0156 (7)−0.0004 (5)0.0034 (5)−0.0013 (5)
C60.0162 (6)0.0127 (6)0.0116 (6)−0.0003 (5)0.0009 (5)−0.0009 (5)
C70.0144 (6)0.0139 (6)0.0116 (6)−0.0012 (5)0.0019 (5)0.0004 (5)
C80.0140 (5)0.0147 (6)0.0104 (6)0.0008 (5)0.0022 (5)−0.0009 (5)
C90.0121 (5)0.0120 (6)0.0130 (6)−0.0003 (4)0.0020 (5)0.0003 (5)
C100.0142 (5)0.0135 (6)0.0097 (6)−0.0012 (5)0.0022 (4)0.0003 (5)
C110.0144 (6)0.0128 (6)0.0126 (6)−0.0002 (5)0.0041 (5)−0.0009 (5)
C120.0142 (6)0.0134 (6)0.0146 (6)0.0010 (5)0.0023 (5)0.0007 (5)
C130.0135 (5)0.0175 (6)0.0118 (6)0.0011 (5)0.0045 (5)0.0011 (5)
C140.0180 (6)0.0188 (7)0.0137 (6)−0.0013 (5)0.0045 (5)−0.0007 (5)
C150.0165 (6)0.0185 (7)0.0142 (7)0.0013 (5)0.0033 (5)0.0008 (5)
C160.0150 (6)0.0197 (7)0.0121 (6)0.0020 (5)0.0022 (5)−0.0001 (5)
C170.0178 (6)0.0207 (7)0.0136 (7)0.0003 (5)0.0033 (5)0.0020 (5)
C180.0202 (6)0.0276 (8)0.0136 (7)0.0005 (6)0.0023 (5)−0.0027 (6)
C190.0198 (7)0.0236 (7)0.0193 (7)−0.0006 (6)0.0021 (5)−0.0050 (6)
C200.0229 (7)0.0204 (7)0.0210 (8)−0.0019 (6)0.0067 (6)0.0000 (6)
C210.0218 (7)0.0221 (7)0.0126 (7)0.0006 (6)0.0039 (5)0.0008 (5)
C220.0134 (5)0.0141 (6)0.0110 (6)0.0004 (5)0.0048 (5)0.0010 (5)
C230.0155 (6)0.0148 (6)0.0148 (6)−0.0003 (5)0.0050 (5)0.0005 (5)
C240.0205 (6)0.0134 (6)0.0160 (7)0.0013 (5)0.0080 (5)0.0003 (5)
C250.0198 (6)0.0175 (6)0.0142 (7)0.0065 (5)0.0071 (5)0.0050 (5)
C260.0163 (6)0.0203 (7)0.0122 (6)0.0026 (5)0.0030 (5)0.0025 (5)
C270.0156 (6)0.0156 (6)0.0119 (6)0.0005 (5)0.0039 (5)−0.0001 (5)
C280.0215 (7)0.0156 (6)0.0213 (7)0.0049 (5)0.0061 (6)−0.0020 (5)

Geometric parameters (Å, º)

F1—C31.3680 (16)C14—C151.339 (2)
F2—C251.3604 (16)C14—H14A0.9500
F3—C171.3636 (17)C15—C161.464 (2)
O1—C111.3681 (16)C15—H15A0.9500
O1—C281.4304 (17)C16—C171.392 (2)
O2—C131.2213 (17)C16—C211.400 (2)
C1—C21.389 (2)C17—C181.384 (2)
C1—C61.3994 (18)C18—C191.386 (2)
C1—H1A0.9500C18—H18A0.9500
C2—C31.377 (2)C19—C201.392 (2)
C2—H2A0.9500C19—H19A0.9500
C3—C41.377 (2)C20—C211.384 (2)
C4—C51.389 (2)C20—H20A0.9500
C4—H4A0.9500C21—H21A0.9500
C5—C61.397 (2)C22—C271.3970 (18)
C5—H5A0.9500C22—C231.4002 (19)
C6—C71.4874 (19)C23—C241.3915 (19)
C7—C81.3965 (18)C23—H23A0.9500
C7—C121.3975 (19)C24—C251.377 (2)
C8—C91.3976 (19)C24—H24A0.9500
C8—H8A0.9500C25—C261.381 (2)
C9—C101.4069 (19)C26—C271.3888 (19)
C9—C221.4913 (18)C26—H26A0.9500
C10—C111.4033 (18)C27—H27A0.9500
C10—C131.5052 (18)C28—H28A0.9800
C11—C121.3897 (19)C28—H28B0.9800
C12—H12A0.9500C28—H28C0.9800
C13—C141.483 (2)
C11—O1—C28118.02 (11)C14—C15—H15A117.6
C2—C1—C6120.80 (13)C16—C15—H15A117.6
C2—C1—H1A119.6C17—C16—C21115.84 (13)
C6—C1—H1A119.6C17—C16—C15120.70 (13)
C3—C2—C1118.16 (13)C21—C16—C15123.46 (13)
C3—C2—H2A120.9F3—C17—C18117.82 (13)
C1—C2—H2A120.9F3—C17—C16118.36 (13)
F1—C3—C2118.31 (13)C18—C17—C16123.82 (14)
F1—C3—C4118.41 (13)C17—C18—C19118.52 (14)
C2—C3—C4123.28 (13)C17—C18—H18A120.7
C3—C4—C5117.85 (13)C19—C18—H18A120.7
C3—C4—H4A121.1C18—C19—C20119.87 (14)
C5—C4—H4A121.1C18—C19—H19A120.1
C4—C5—C6121.16 (13)C20—C19—H19A120.1
C4—C5—H5A119.4C21—C20—C19119.98 (15)
C6—C5—H5A119.4C21—C20—H20A120.0
C5—C6—C1118.73 (13)C19—C20—H20A120.0
C5—C6—C7121.22 (12)C20—C21—C16121.94 (14)
C1—C6—C7120.01 (12)C20—C21—H21A119.0
C8—C7—C12119.53 (12)C16—C21—H21A119.0
C8—C7—C6120.15 (12)C27—C22—C23118.31 (12)
C12—C7—C6120.26 (12)C27—C22—C9122.07 (12)
C7—C8—C9121.46 (12)C23—C22—C9119.60 (12)
C7—C8—H8A119.3C24—C23—C22121.41 (13)
C9—C8—H8A119.3C24—C23—H23A119.3
C8—C9—C10118.89 (12)C22—C23—H23A119.3
C8—C9—C22118.91 (12)C25—C24—C23117.96 (13)
C10—C9—C22122.19 (12)C25—C24—H24A121.0
C11—C10—C9119.23 (12)C23—C24—H24A121.0
C11—C10—C13117.63 (12)F2—C25—C24118.89 (13)
C9—C10—C13123.06 (12)F2—C25—C26118.28 (13)
O1—C11—C12123.78 (12)C24—C25—C26122.82 (13)
O1—C11—C10114.71 (12)C25—C26—C27118.37 (13)
C12—C11—C10121.40 (12)C25—C26—H26A120.8
C11—C12—C7119.38 (12)C27—C26—H26A120.8
C11—C12—H12A120.3C26—C27—C22121.09 (13)
C7—C12—H12A120.3C26—C27—H27A119.5
O2—C13—C14122.67 (13)C22—C27—H27A119.5
O2—C13—C10120.84 (13)O1—C28—H28A109.5
C14—C13—C10116.49 (12)O1—C28—H28B109.5
C15—C14—C13122.55 (14)H28A—C28—H28B109.5
C15—C14—H14A118.7O1—C28—H28C109.5
C13—C14—H14A118.7H28A—C28—H28C109.5
C14—C15—C16124.73 (14)H28B—C28—H28C109.5
C6—C1—C2—C31.1 (2)C9—C10—C13—O253.22 (19)
C1—C2—C3—F1−179.81 (12)C11—C10—C13—C1456.61 (16)
C1—C2—C3—C40.1 (2)C9—C10—C13—C14−126.59 (14)
F1—C3—C4—C5178.50 (12)O2—C13—C14—C1510.3 (2)
C2—C3—C4—C5−1.4 (2)C10—C13—C14—C15−169.89 (13)
C3—C4—C5—C61.5 (2)C13—C14—C15—C16179.83 (13)
C4—C5—C6—C1−0.4 (2)C14—C15—C16—C17175.82 (14)
C4—C5—C6—C7−177.98 (13)C14—C15—C16—C21−3.2 (2)
C2—C1—C6—C5−1.0 (2)C21—C16—C17—F3−179.05 (12)
C2—C1—C6—C7176.65 (13)C15—C16—C17—F31.8 (2)
C5—C6—C7—C847.62 (19)C21—C16—C17—C181.6 (2)
C1—C6—C7—C8−129.95 (14)C15—C16—C17—C18−177.46 (14)
C5—C6—C7—C12−135.25 (14)F3—C17—C18—C19−179.43 (13)
C1—C6—C7—C1247.18 (19)C16—C17—C18—C19−0.1 (2)
C12—C7—C8—C9−2.8 (2)C17—C18—C19—C20−1.2 (2)
C6—C7—C8—C9174.33 (12)C18—C19—C20—C210.9 (2)
C7—C8—C9—C101.9 (2)C19—C20—C21—C160.7 (2)
C7—C8—C9—C22−178.15 (12)C17—C16—C21—C20−1.9 (2)
C8—C9—C10—C111.05 (19)C15—C16—C21—C20177.15 (13)
C22—C9—C10—C11−178.94 (12)C8—C9—C22—C27−136.61 (14)
C8—C9—C10—C13−175.70 (12)C10—C9—C22—C2743.38 (19)
C22—C9—C10—C134.3 (2)C8—C9—C22—C2342.13 (18)
C28—O1—C11—C1215.75 (19)C10—C9—C22—C23−137.88 (14)
C28—O1—C11—C10−167.98 (12)C27—C22—C23—C24−1.9 (2)
C9—C10—C11—O1−179.40 (12)C9—C22—C23—C24179.29 (12)
C13—C10—C11—O1−2.47 (17)C22—C23—C24—C250.8 (2)
C9—C10—C11—C12−3.0 (2)C23—C24—C25—F2−179.19 (12)
C13—C10—C11—C12173.89 (12)C23—C24—C25—C260.5 (2)
O1—C11—C12—C7178.11 (12)F2—C25—C26—C27179.10 (12)
C10—C11—C12—C72.1 (2)C24—C25—C26—C27−0.6 (2)
C8—C7—C12—C110.8 (2)C25—C26—C27—C22−0.6 (2)
C6—C7—C12—C11−176.31 (12)C23—C22—C27—C261.8 (2)
C11—C10—C13—O2−123.58 (14)C9—C22—C27—C26−179.42 (13)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C7–C12 ring.

D—H···AD—HH···AD···AD—H···A
C4—H4A···O2i0.952.403.3008 (18)158
C19—H19A···F2ii0.952.543.2326 (18)130
C24—H24A···Cg1iii0.952.843.4579 (15)124
C28—H28C···Cg1iv0.982.863.5461 (16)128

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−3/2, −z+3/2; (iii) x, y+1, z; (iv) −x+2, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5146).

References

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