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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 5| May 2012| Pages o1560-o1561

(2E)-1-(4,4′′-Di­fluoro-5′-meth­­oxy-1,1′:3′,1′′-terphenyl-4′-yl)-3-(2,6-di­fluoro­phen­yl)prop-2-en-1-one

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

(Received 23 April 2012; accepted 23 April 2012; online 28 April 2012)

In the title compound, C28H18F4O2, the central benzene ring makes dihedral angles of 44.27 (6), 56.33 (5) and 77.27 (6)° with the two adjacent fluoro­benzene rings and terminal difluoro-substituted benzene ring, respectively. The dihedral angle between the fluoro­benzene rings is 87.81 (6)°. The meth­oxy and prop-2-en-1-one groups are essentially coplanar with their attached benzene rings, as indicated by their C—O—Car—Car [−0.06 (15)°] and C—C—Car—Car [4.5 (2)°] (ar = aromatic) torsion angles. In the crystal, mol­ecules are linked by C—H⋯F and C—H⋯O hydrogen bonds into sheets lying parallel to the ac plane. The crystal structure also features C—H⋯π inter­actions.

Related literature

For related structures and background to terphenyl chalcones, see: Fun et al. (2011[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3327-o3328.], 2012[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o163.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C28H18F4O2

  • Mr = 462.42

  • Triclinic, [P \overline 1]

  • a = 8.9624 (5) Å

  • b = 10.2127 (6) Å

  • c = 13.3281 (7) Å

  • α = 67.780 (1)°

  • β = 86.776 (1)°

  • γ = 85.293 (1)°

  • V = 1125.10 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 K

  • 0.25 × 0.20 × 0.11 mm

Data collection
  • Bruker APEX Duo CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.974, Tmax = 0.989

  • 28220 measured reflections

  • 8063 independent reflections

  • 6097 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.144

  • S = 1.02

  • 8063 reflections

  • 308 parameters

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2A⋯F3i 0.93 2.46 3.3655 (18) 164
C8—H8A⋯F4ii 0.93 2.45 3.3726 (13) 170
C24—H24A⋯O2iii 0.93 2.57 3.4371 (14) 155
C20—H20ACg1iv 0.93 2.83 3.5082 (14) 130
C27—H27ACg2v 0.93 2.68 3.4068 (12) 136
C28—H28BCg2vi 0.96 2.90 3.7990 (15) 157
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y+2, -z; (iii) x+1, y, z; (iv) -x+1, -y+1, -z; (v) -x, -y+2, -z; (vi) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

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 et al., 2012).

In the title compound (Fig. 1), the central benzene ring (C7–C12) makes dihedral angles of 44.27 (6), 56.33 (5) and 77.27 (6)° with the two adjacent fluoro-substituted benzene rings (C1–C6 & C22–C27) and terminal difluoro-substituted benzene ring (C16–C21), respectively. The dihedral angle between the fluoro-substituted benzene rings is 87.81 (6)°. The methoxy (O1/C28) and prop-2-en-1-one (O2/C13–C15) groups are essentially coplanar with C7–C12 and C16–C21 rings, respectively as indicated by their torsion angles C28—O1—C11—C12 = -0.06 (15)° and C14—C15—C16—C17 = 4.5 (2)°. Bond lengths and angles are comparable to those in related structures (Fun et al., 2011,, 2012).

In the crystal (Fig. 2), molecules are linked by C2—H2A···F3, C8—H8A···F4 and C24—H24A···O2 hydrogen bonds (Table 1) into two dimensional networks parallel to ac plane. The crystal also features C—H···π interactions (Table 1), involving Cg1 and Cg2 which are the centroids of C1—C6 and C7—C12 rings, respectively.

Related literature top

For related structures and background to terphenyl chalcones, see: Fun et al. (2011, 2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987).

Experimental top

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 2,6-difluorobenzaldehyde (0.142 g, 0.001 mol) in 30 ml e thanol, 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 then purified by recrystallization from ethanol. Colourless blocks were grown from acetone solution by slow evaporation and the yield of the compound was 72% (m.p.: 405 K).

Refinement top

All H atoms were positioned geometrically [C—H = 0.93 and 0.96 Å] and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating group model was applied to the methyl group. Three outliers (4 - 5 1), (0 - 3 2) and (3 - 5 2) were omitted.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds.
(2E)- 1-(4,4''-Difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl)-3- (2,6-difluorophenyl)prop-2-en-1-one top
Crystal data top
C28H18F4O2Z = 2
Mr = 462.42F(000) = 476
Triclinic, P1Dx = 1.365 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9624 (5) ÅCell parameters from 7563 reflections
b = 10.2127 (6) Åθ = 2.3–32.4°
c = 13.3281 (7) ŵ = 0.11 mm1
α = 67.780 (1)°T = 100 K
β = 86.776 (1)°Block, colourless
γ = 85.293 (1)°0.25 × 0.20 × 0.11 mm
V = 1125.10 (11) Å3
Data collection top
Bruker APEX Duo CCD
diffractometer
8063 independent reflections
Radiation source: fine-focus sealed tube6097 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ϕ and ω scansθmax = 32.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1313
Tmin = 0.974, Tmax = 0.989k = 1514
28220 measured reflectionsl = 2018
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0774P)2 + 0.2553P]
where P = (Fo2 + 2Fc2)/3
8063 reflections(Δ/σ)max < 0.001
308 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C28H18F4O2γ = 85.293 (1)°
Mr = 462.42V = 1125.10 (11) Å3
Triclinic, P1Z = 2
a = 8.9624 (5) ÅMo Kα radiation
b = 10.2127 (6) ŵ = 0.11 mm1
c = 13.3281 (7) ÅT = 100 K
α = 67.780 (1)°0.25 × 0.20 × 0.11 mm
β = 86.776 (1)°
Data collection top
Bruker APEX Duo CCD
diffractometer
8063 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
6097 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.989Rint = 0.035
28220 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.144H-atom parameters constrained
S = 1.02Δρmax = 0.40 e Å3
8063 reflectionsΔρmin = 0.35 e Å3
308 parameters
Special details top

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) top
xyzUiso*/Ueq
F10.17366 (10)0.87097 (10)0.57879 (6)0.03431 (19)
F20.40523 (9)0.37977 (9)0.20352 (6)0.03302 (19)
F30.15771 (9)0.45771 (9)0.49909 (6)0.03172 (19)
F40.54429 (8)0.99409 (9)0.24888 (6)0.02763 (17)
O10.18938 (9)0.62125 (9)0.08627 (7)0.02127 (17)
O20.12638 (9)0.79463 (9)0.21502 (7)0.02271 (17)
C10.09479 (14)0.69493 (13)0.29224 (10)0.0227 (2)
H1A0.07110.60600.24300.027*
C20.11646 (14)0.71665 (14)0.40139 (10)0.0261 (2)
H2A0.10740.64370.42590.031*
C30.15174 (13)0.84918 (14)0.47200 (9)0.0240 (2)
C40.16684 (13)0.96077 (13)0.43948 (9)0.0221 (2)
H4A0.19121.04900.48950.027*
C50.14462 (12)0.93777 (12)0.32982 (9)0.0187 (2)
H5A0.15421.01130.30610.022*
C60.10798 (12)0.80452 (11)0.25527 (8)0.01738 (19)
C70.08139 (12)0.78028 (11)0.13880 (9)0.01654 (19)
C80.17578 (12)0.83272 (11)0.08525 (8)0.01669 (19)
H8A0.25810.88090.12240.020*
C90.14842 (11)0.81386 (11)0.02356 (8)0.01554 (18)
C100.02237 (11)0.74476 (11)0.07864 (8)0.01598 (19)
C110.07150 (11)0.68975 (11)0.02521 (9)0.01676 (19)
C120.04140 (12)0.70569 (11)0.08225 (9)0.01702 (19)
H12A0.10250.66700.11650.020*
C130.01691 (11)0.72807 (11)0.19450 (9)0.01693 (19)
C140.07608 (12)0.62893 (12)0.28288 (9)0.0188 (2)
H14A0.06010.62900.35240.023*
C150.18306 (12)0.53861 (11)0.26616 (9)0.0178 (2)
H15A0.20000.54740.19450.021*
C160.27629 (12)0.42826 (12)0.34593 (9)0.0182 (2)
C170.26488 (13)0.38889 (13)0.45849 (9)0.0218 (2)
C180.35385 (14)0.28272 (14)0.53126 (10)0.0256 (2)
H18A0.34120.26080.60540.031*
C190.46305 (14)0.20924 (14)0.49095 (10)0.0279 (3)
H19A0.52470.13770.53860.033*
C200.48077 (14)0.24180 (14)0.38016 (10)0.0275 (3)
H20A0.55330.19270.35280.033*
C210.38792 (13)0.34881 (13)0.31183 (9)0.0221 (2)
C220.25400 (11)0.86676 (11)0.07971 (8)0.01586 (19)
C230.40626 (12)0.82182 (12)0.08352 (9)0.0199 (2)
H23A0.44140.76290.04740.024*
C240.50582 (12)0.86360 (13)0.14022 (9)0.0224 (2)
H24A0.60660.83280.14350.027*
C250.44924 (12)0.95271 (12)0.19155 (9)0.0201 (2)
C260.30110 (13)1.00312 (12)0.18763 (9)0.0202 (2)
H26A0.26781.06500.22170.024*
C270.20311 (12)0.95877 (11)0.13136 (9)0.0182 (2)
H27A0.10260.99080.12810.022*
C280.28775 (13)0.56257 (13)0.03620 (10)0.0231 (2)
H28A0.36410.51570.08770.035*
H28B0.23190.49550.01170.035*
H28C0.33340.63710.02450.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0361 (4)0.0511 (5)0.0166 (3)0.0008 (4)0.0005 (3)0.0142 (3)
F20.0317 (4)0.0454 (5)0.0188 (3)0.0145 (3)0.0004 (3)0.0119 (3)
F30.0370 (4)0.0357 (4)0.0187 (3)0.0152 (3)0.0003 (3)0.0097 (3)
F40.0223 (3)0.0393 (4)0.0230 (3)0.0097 (3)0.0061 (3)0.0114 (3)
O10.0178 (4)0.0265 (4)0.0193 (4)0.0074 (3)0.0010 (3)0.0073 (3)
O20.0168 (4)0.0280 (4)0.0234 (4)0.0035 (3)0.0005 (3)0.0108 (3)
C10.0253 (5)0.0232 (5)0.0213 (5)0.0032 (4)0.0009 (4)0.0099 (4)
C20.0286 (6)0.0317 (6)0.0230 (5)0.0022 (5)0.0014 (4)0.0160 (5)
C30.0204 (5)0.0365 (6)0.0152 (5)0.0014 (4)0.0014 (4)0.0105 (4)
C40.0188 (5)0.0264 (5)0.0177 (5)0.0002 (4)0.0017 (4)0.0046 (4)
C50.0164 (4)0.0209 (5)0.0180 (5)0.0001 (4)0.0020 (4)0.0064 (4)
C60.0151 (4)0.0207 (5)0.0164 (4)0.0002 (3)0.0016 (3)0.0070 (4)
C70.0160 (4)0.0169 (4)0.0166 (4)0.0005 (3)0.0018 (3)0.0063 (4)
C80.0144 (4)0.0188 (4)0.0165 (4)0.0007 (3)0.0003 (3)0.0063 (4)
C90.0125 (4)0.0172 (4)0.0167 (4)0.0013 (3)0.0018 (3)0.0063 (4)
C100.0141 (4)0.0173 (4)0.0156 (4)0.0011 (3)0.0019 (3)0.0054 (4)
C110.0145 (4)0.0170 (4)0.0173 (4)0.0007 (3)0.0008 (3)0.0048 (4)
C120.0160 (4)0.0179 (4)0.0174 (4)0.0012 (3)0.0023 (3)0.0067 (4)
C130.0145 (4)0.0187 (4)0.0178 (5)0.0014 (3)0.0007 (3)0.0070 (4)
C140.0175 (5)0.0228 (5)0.0156 (4)0.0006 (4)0.0010 (4)0.0070 (4)
C150.0167 (4)0.0201 (5)0.0157 (4)0.0007 (4)0.0011 (3)0.0056 (4)
C160.0161 (4)0.0210 (5)0.0169 (5)0.0000 (4)0.0010 (4)0.0067 (4)
C170.0215 (5)0.0239 (5)0.0191 (5)0.0035 (4)0.0005 (4)0.0081 (4)
C180.0260 (6)0.0292 (6)0.0180 (5)0.0046 (4)0.0031 (4)0.0058 (4)
C190.0242 (6)0.0306 (6)0.0235 (6)0.0067 (5)0.0042 (4)0.0053 (5)
C200.0220 (5)0.0328 (6)0.0239 (6)0.0095 (5)0.0010 (4)0.0086 (5)
C210.0190 (5)0.0283 (5)0.0173 (5)0.0034 (4)0.0003 (4)0.0079 (4)
C220.0130 (4)0.0187 (4)0.0149 (4)0.0010 (3)0.0015 (3)0.0050 (4)
C230.0145 (4)0.0244 (5)0.0213 (5)0.0008 (4)0.0011 (4)0.0094 (4)
C240.0130 (4)0.0305 (6)0.0222 (5)0.0002 (4)0.0033 (4)0.0082 (4)
C250.0180 (5)0.0254 (5)0.0158 (4)0.0059 (4)0.0043 (4)0.0050 (4)
C260.0206 (5)0.0220 (5)0.0192 (5)0.0026 (4)0.0009 (4)0.0087 (4)
C270.0147 (4)0.0203 (5)0.0194 (5)0.0008 (3)0.0024 (3)0.0072 (4)
C280.0171 (5)0.0268 (5)0.0276 (6)0.0058 (4)0.0004 (4)0.0117 (5)
Geometric parameters (Å, º) top
F1—C31.3602 (13)C13—C141.4756 (15)
F2—C211.3585 (13)C14—C151.3440 (15)
F3—C171.3519 (13)C14—H14A0.9300
F4—C251.3656 (13)C15—C161.4621 (15)
O1—C111.3645 (13)C15—H15A0.9300
O1—C281.4274 (14)C16—C171.3985 (15)
O2—C131.2249 (13)C16—C211.4002 (15)
C1—C21.3908 (16)C17—C181.3791 (16)
C1—C61.3981 (16)C18—C191.3910 (17)
C1—H1A0.9300C18—H18A0.9300
C2—C31.3751 (18)C19—C201.3882 (17)
C2—H2A0.9300C19—H19A0.9300
C3—C41.3823 (18)C20—C211.3782 (16)
C4—C51.3951 (15)C20—H20A0.9300
C4—H4A0.9300C22—C271.3958 (15)
C5—C61.4003 (15)C22—C231.4010 (14)
C5—H5A0.9300C23—C241.3897 (16)
C6—C71.4850 (15)C23—H23A0.9300
C7—C81.3939 (15)C24—C251.3819 (17)
C7—C121.4034 (15)C24—H24A0.9300
C8—C91.3990 (14)C25—C261.3805 (16)
C8—H8A0.9300C26—C271.3912 (15)
C9—C101.3996 (14)C26—H26A0.9300
C9—C221.4888 (15)C27—H27A0.9300
C10—C111.4064 (15)C28—H28A0.9600
C10—C131.5123 (14)C28—H28B0.9600
C11—C121.3921 (15)C28—H28C0.9600
C12—H12A0.9300
C11—O1—C28117.58 (9)C14—C15—H15A115.8
C2—C1—C6121.10 (11)C16—C15—H15A115.8
C2—C1—H1A119.5C17—C16—C21113.73 (10)
C6—C1—H1A119.5C17—C16—C15126.22 (10)
C3—C2—C1118.01 (11)C21—C16—C15120.04 (10)
C3—C2—H2A121.0F3—C17—C18117.61 (10)
C1—C2—H2A121.0F3—C17—C16117.92 (10)
F1—C3—C2118.31 (11)C18—C17—C16124.46 (10)
F1—C3—C4118.56 (11)C17—C18—C19118.36 (11)
C2—C3—C4123.13 (11)C17—C18—H18A120.8
C3—C4—C5118.34 (11)C19—C18—H18A120.8
C3—C4—H4A120.8C20—C19—C18120.55 (11)
C5—C4—H4A120.8C20—C19—H19A119.7
C4—C5—C6120.35 (11)C18—C19—H19A119.7
C4—C5—H5A119.8C21—C20—C19118.19 (11)
C6—C5—H5A119.8C21—C20—H20A120.9
C1—C6—C5119.07 (10)C19—C20—H20A120.9
C1—C6—C7120.38 (10)F2—C21—C20117.95 (10)
C5—C6—C7120.55 (10)F2—C21—C16117.34 (10)
C8—C7—C12119.51 (10)C20—C21—C16124.70 (11)
C8—C7—C6120.74 (9)C27—C22—C23118.94 (10)
C12—C7—C6119.75 (10)C27—C22—C9120.92 (9)
C7—C8—C9120.89 (10)C23—C22—C9120.12 (9)
C7—C8—H8A119.6C24—C23—C22121.32 (10)
C9—C8—H8A119.6C24—C23—H23A119.3
C8—C9—C10119.59 (10)C22—C23—H23A119.3
C8—C9—C22119.71 (9)C25—C24—C23117.43 (10)
C10—C9—C22120.71 (9)C25—C24—H24A121.3
C9—C10—C11119.51 (9)C23—C24—H24A121.3
C9—C10—C13121.81 (9)F4—C25—C26117.91 (10)
C11—C10—C13118.68 (9)F4—C25—C24118.65 (10)
O1—C11—C12124.20 (10)C26—C25—C24123.44 (11)
O1—C11—C10115.25 (9)C25—C26—C27118.14 (10)
C12—C11—C10120.55 (10)C25—C26—H26A120.9
C11—C12—C7119.86 (10)C27—C26—H26A120.9
C11—C12—H12A120.1C26—C27—C22120.70 (10)
C7—C12—H12A120.1C26—C27—H27A119.7
O2—C13—C14120.22 (10)C22—C27—H27A119.7
O2—C13—C10120.30 (9)O1—C28—H28A109.5
C14—C13—C10119.47 (9)O1—C28—H28B109.5
C15—C14—C13122.15 (10)H28A—C28—H28B109.5
C15—C14—H14A118.9O1—C28—H28C109.5
C13—C14—H14A118.9H28A—C28—H28C109.5
C14—C15—C16128.48 (10)H28B—C28—H28C109.5
C6—C1—C2—C30.19 (18)C11—C10—C13—C14109.02 (11)
C1—C2—C3—F1179.74 (11)O2—C13—C14—C15169.89 (11)
C1—C2—C3—C40.16 (19)C10—C13—C14—C158.99 (16)
F1—C3—C4—C5179.84 (10)C13—C14—C15—C16175.29 (11)
C2—C3—C4—C50.25 (18)C14—C15—C16—C174.5 (2)
C3—C4—C5—C60.00 (16)C14—C15—C16—C21176.78 (12)
C2—C1—C6—C50.43 (17)C21—C16—C17—F3178.53 (11)
C2—C1—C6—C7178.74 (10)C15—C16—C17—F30.30 (18)
C4—C5—C6—C10.33 (16)C21—C16—C17—C180.26 (18)
C4—C5—C6—C7178.83 (10)C15—C16—C17—C18179.09 (12)
C1—C6—C7—C8137.19 (11)F3—C17—C18—C19178.96 (12)
C5—C6—C7—C843.66 (14)C16—C17—C18—C190.2 (2)
C1—C6—C7—C1243.81 (15)C17—C18—C19—C200.4 (2)
C5—C6—C7—C12135.34 (11)C18—C19—C20—C210.3 (2)
C12—C7—C8—C90.99 (15)C19—C20—C21—F2179.68 (12)
C6—C7—C8—C9178.01 (9)C19—C20—C21—C160.2 (2)
C7—C8—C9—C101.73 (15)C17—C16—C21—F2179.42 (11)
C7—C8—C9—C22177.95 (9)C15—C16—C21—F20.51 (17)
C8—C9—C10—C112.77 (15)C17—C16—C21—C200.45 (18)
C22—C9—C10—C11176.91 (9)C15—C16—C21—C20179.36 (12)
C8—C9—C10—C13176.84 (9)C8—C9—C22—C27125.20 (11)
C22—C9—C10—C133.48 (15)C10—C9—C22—C2755.12 (14)
C28—O1—C11—C120.06 (15)C8—C9—C22—C2356.29 (14)
C28—O1—C11—C10179.63 (9)C10—C9—C22—C23123.38 (11)
C9—C10—C11—O1178.46 (9)C27—C22—C23—C241.97 (16)
C13—C10—C11—O11.92 (14)C9—C22—C23—C24176.57 (10)
C9—C10—C11—C121.12 (15)C22—C23—C24—C250.82 (17)
C13—C10—C11—C12178.50 (9)C23—C24—C25—F4179.25 (10)
O1—C11—C12—C7178.86 (10)C23—C24—C25—C261.08 (18)
C10—C11—C12—C71.60 (15)F4—C25—C26—C27178.59 (10)
C8—C7—C12—C112.64 (15)C24—C25—C26—C271.74 (17)
C6—C7—C12—C11176.37 (9)C25—C26—C27—C220.51 (16)
C9—C10—C13—O2109.75 (12)C23—C22—C27—C261.27 (16)
C11—C10—C13—O269.86 (14)C9—C22—C27—C26177.25 (10)
C9—C10—C13—C1471.37 (14)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2A···F3i0.932.463.3655 (18)164
C8—H8A···F4ii0.932.453.3726 (13)170
C24—H24A···O2iii0.932.573.4371 (14)155
C20—H20A···Cg1iv0.932.833.5082 (14)130
C27—H27A···Cg2v0.932.683.4068 (12)136
C28—H28B···Cg2vi0.962.903.7990 (15)157
Symmetry codes: (i) x, y, z1; (ii) x+1, y+2, z; (iii) x+1, y, z; (iv) x+1, y+1, z; (v) x, y+2, z; (vi) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC28H18F4O2
Mr462.42
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)8.9624 (5), 10.2127 (6), 13.3281 (7)
α, β, γ (°)67.780 (1), 86.776 (1), 85.293 (1)
V3)1125.10 (11)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.25 × 0.20 × 0.11
Data collection
DiffractometerBruker APEX Duo CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.974, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
28220, 8063, 6097
Rint0.035
(sin θ/λ)max1)0.757
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.144, 1.02
No. of reflections8063
No. of parameters308
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2A···F3i0.932.463.3655 (18)164
C8—H8A···F4ii0.932.453.3726 (13)170
C24—H24A···O2iii0.932.573.4371 (14)155
C20—H20A···Cg1iv0.932.833.5082 (14)130
C27—H27A···Cg2v0.932.683.4068 (12)136
C28—H28B···Cg2vi0.962.903.7990 (15)157
Symmetry codes: (i) x, y, z1; (ii) x+1, y+2, z; (iii) x+1, y, z; (iv) x+1, y+1, z; (v) x, y+2, z; (vi) x, y+1, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a 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 the research facilities.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationFun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3327–o3328.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o163.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Pages o1560-o1561
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