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In the crystal structure of the title compound, C18H16, the dihedral angle between the least-squares planes through the C atoms of the phenyl rings is 2.82 (4)°. The bond length of the central double bond is 1.3297 (15) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011492/bt6158sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011492/bt6158Isup2.hkl
Contains datablock I

CCDC reference: 193732

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.068
  • Data-to-parameter ratio = 17.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).

(I) top
Crystal data top
C18H16F(000) = 992
Mr = 232.31Dx = 1.200 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 27.0655 (6) ÅCell parameters from 12358 reflections
b = 5.6822 (2) Åθ = 3.1–27.5°
c = 19.3829 (6) ŵ = 0.07 mm1
β = 120.3936 (18)°T = 291 K
V = 2571.26 (13) Å3Needle, colourless
Z = 80.5 × 0.1 × 0.1 mm
Data collection top
Nonius KappaCCD
diffractometer
1262 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
Detector resolution: 19 vertical, 18 horizontal pixels mm-1h = 3434
310 frames via ω–rotation (Δω=1°) and two times 90 s per frame (three sets at different κ–angles) scansk = 77
12358 measured reflectionsl = 2421
2909 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.0083P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
2909 reflectionsΔρmax = 0.14 e Å3
164 parametersΔρmin = 0.10 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00177 (17)
Special details top

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
C10.01129 (6)0.9091 (2)0.11726 (7)0.0496 (3)
C20.04292 (5)0.7075 (2)0.10522 (7)0.0565 (4)
H2A0.02500.55800.10340.068*
H2B0.04350.72740.05590.068*
C30.10220 (5)0.7192 (2)0.17619 (7)0.0530 (3)
C40.14894 (6)0.5769 (2)0.19578 (8)0.0702 (4)
H40.14560.45050.16320.084*
C50.20049 (6)0.6235 (3)0.26380 (9)0.0822 (5)
H50.23200.52820.27710.099*
C60.20569 (6)0.8104 (3)0.31228 (8)0.0812 (5)
H60.24080.84100.35790.097*
C70.15933 (6)0.9526 (2)0.29386 (7)0.0675 (4)
H70.16291.07840.32680.081*
C80.10767 (5)0.9054 (2)0.22590 (7)0.0518 (3)
C90.05212 (5)1.0334 (2)0.19487 (7)0.0564 (4)
H9A0.05631.19780.18530.068*
H9B0.03851.02350.23250.068*
C110.04340 (5)0.9592 (2)0.06635 (7)0.0493 (3)
C120.07987 (5)0.8199 (2)0.00970 (7)0.0604 (4)
H12A0.08110.65540.00270.073*
H12B0.06430.83110.04490.073*
C130.14022 (5)0.9279 (2)0.04966 (7)0.0716 (4)
H13A0.15140.98790.10240.086*
H13B0.16820.81240.05450.086*
C140.13528 (6)1.1240 (2)0.00527 (8)0.0607 (4)
C150.17814 (6)1.2728 (3)0.00328 (9)0.0784 (5)
H150.21501.25830.04710.094*
C160.16608 (7)1.4430 (3)0.05347 (11)0.0846 (5)
H160.19511.54240.04820.102*
C170.11107 (7)1.4681 (3)0.11852 (9)0.0772 (4)
H170.10321.58540.15620.093*
C180.06778 (6)1.3179 (2)0.12728 (7)0.0625 (4)
H180.03081.33430.17070.075*
C190.08008 (5)1.1424 (2)0.07062 (7)0.0526 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0510 (9)0.0489 (8)0.0482 (7)0.0008 (7)0.0245 (7)0.0014 (6)
C20.0581 (9)0.0520 (8)0.0572 (8)0.0002 (7)0.0275 (7)0.0007 (7)
C30.0499 (9)0.0514 (9)0.0550 (8)0.0013 (7)0.0247 (7)0.0025 (7)
C40.0620 (10)0.0652 (10)0.0744 (10)0.0079 (8)0.0280 (9)0.0078 (8)
C50.0585 (11)0.0820 (13)0.0912 (12)0.0146 (8)0.0270 (10)0.0059 (9)
C60.0530 (10)0.0872 (12)0.0789 (10)0.0044 (9)0.0152 (8)0.0067 (9)
C70.0570 (10)0.0656 (10)0.0667 (9)0.0015 (8)0.0218 (8)0.0092 (7)
C80.0469 (9)0.0530 (9)0.0513 (8)0.0002 (7)0.0217 (7)0.0026 (7)
C90.0541 (9)0.0557 (9)0.0557 (8)0.0018 (7)0.0251 (7)0.0011 (7)
C110.0485 (9)0.0497 (9)0.0493 (7)0.0006 (7)0.0244 (7)0.0050 (6)
C120.0565 (9)0.0604 (9)0.0572 (8)0.0058 (7)0.0235 (7)0.0018 (7)
C130.0586 (10)0.0723 (11)0.0674 (9)0.0042 (8)0.0196 (8)0.0092 (8)
C140.0519 (10)0.0659 (10)0.0642 (9)0.0071 (8)0.0294 (8)0.0165 (8)
C150.0613 (11)0.0905 (13)0.0808 (11)0.0108 (10)0.0341 (9)0.0228 (10)
C160.0755 (13)0.0938 (13)0.0988 (12)0.0326 (10)0.0545 (11)0.0345 (11)
C170.0925 (13)0.0747 (11)0.0805 (11)0.0207 (10)0.0556 (11)0.0114 (8)
C180.0667 (10)0.0661 (10)0.0607 (9)0.0115 (8)0.0366 (8)0.0108 (8)
C190.0512 (9)0.0579 (9)0.0514 (8)0.0025 (7)0.0279 (8)0.0118 (7)
Geometric parameters (Å, º) top
C1—C111.3297 (15)C11—C191.4696 (16)
C1—C91.5169 (14)C11—C121.5171 (15)
C1—C21.5169 (15)C12—C131.5376 (15)
C2—C31.4958 (16)C12—H12A0.9700
C2—H2A0.9700C12—H12B0.9700
C2—H2B0.9700C13—C141.4994 (17)
C3—C41.3828 (16)C13—H13A0.9700
C3—C81.3877 (15)C13—H13B0.9700
C4—C51.3761 (16)C14—C151.3760 (18)
C4—H40.9300C14—C191.3903 (16)
C5—C61.3771 (17)C15—C161.3743 (18)
C5—H50.9300C15—H150.9300
C6—C71.3792 (17)C16—C171.3884 (17)
C6—H60.9300C16—H160.9300
C7—C81.3778 (15)C17—C181.3888 (16)
C7—H70.9300C17—H170.9300
C8—C91.4954 (15)C18—C191.3933 (16)
C9—H9A0.9700C18—H180.9300
C9—H9B0.9700
C11—C1—C9127.95 (11)C1—C11—C19129.81 (11)
C11—C1—C2123.42 (11)C1—C11—C12122.82 (11)
C9—C1—C2108.63 (10)C19—C11—C12107.36 (11)
C3—C2—C1104.56 (10)C11—C12—C13106.52 (10)
C3—C2—H2A110.8C11—C12—H12A110.4
C1—C2—H2A110.8C13—C12—H12A110.4
C3—C2—H2B110.8C11—C12—H12B110.4
C1—C2—H2B110.8C13—C12—H12B110.4
H2A—C2—H2B108.9H12A—C12—H12B108.6
C4—C3—C8119.59 (12)C14—C13—C12104.40 (10)
C4—C3—C2129.29 (12)C14—C13—H13A110.9
C8—C3—C2111.12 (11)C12—C13—H13A110.9
C5—C4—C3119.59 (13)C14—C13—H13B110.9
C5—C4—H4120.2C12—C13—H13B110.9
C3—C4—H4120.2H13A—C13—H13B108.9
C4—C5—C6120.42 (13)C15—C14—C19121.01 (14)
C4—C5—H5119.8C15—C14—C13127.17 (14)
C6—C5—H5119.8C19—C14—C13111.81 (12)
C5—C6—C7120.64 (13)C16—C15—C14119.46 (14)
C5—C6—H6119.7C16—C15—H15120.3
C7—C6—H6119.7C14—C15—H15120.3
C6—C7—C8118.92 (12)C15—C16—C17120.70 (14)
C6—C7—H7120.5C15—C16—H16119.7
C8—C7—H7120.5C17—C16—H16119.7
C7—C8—C3120.84 (12)C16—C17—C18119.91 (14)
C7—C8—C9128.11 (12)C16—C17—H17120.0
C3—C8—C9111.05 (11)C18—C17—H17120.0
C8—C9—C1104.60 (10)C17—C18—C19119.55 (13)
C8—C9—H9A110.8C17—C18—H18120.2
C1—C9—H9A110.8C19—C18—H18120.2
C8—C9—H9B110.8C14—C19—C18119.36 (12)
C1—C9—H9B110.8C14—C19—C11109.90 (12)
H9A—C9—H9B108.9C18—C19—C11130.74 (12)
C11—C1—C2—C3179.95 (11)C2—C1—C11—C120.36 (17)
C9—C1—C2—C30.45 (12)C1—C11—C12—C13178.12 (10)
C1—C2—C3—C4179.99 (12)C19—C11—C12—C130.73 (12)
C1—C2—C3—C80.84 (13)C11—C12—C13—C140.17 (13)
C8—C3—C4—C50.81 (19)C12—C13—C14—C15178.78 (12)
C2—C3—C4—C5178.30 (12)C12—C13—C14—C190.50 (14)
C3—C4—C5—C60.0 (2)C19—C14—C15—C160.3 (2)
C4—C5—C6—C70.5 (2)C13—C14—C15—C16179.53 (13)
C5—C6—C7—C80.3 (2)C14—C15—C16—C170.9 (2)
C6—C7—C8—C30.52 (19)C15—C16—C17—C181.0 (2)
C6—C7—C8—C9179.42 (12)C16—C17—C18—C190.18 (19)
C4—C3—C8—C71.06 (18)C15—C14—C19—C181.46 (19)
C2—C3—C8—C7178.21 (11)C13—C14—C19—C18179.21 (11)
C4—C3—C8—C9178.89 (11)C15—C14—C19—C11178.33 (11)
C2—C3—C8—C91.85 (14)C13—C14—C19—C110.99 (14)
C7—C8—C9—C1178.03 (11)C17—C18—C19—C141.38 (18)
C3—C8—C9—C12.03 (13)C17—C18—C19—C11178.37 (12)
C11—C1—C9—C8178.97 (11)C1—C11—C19—C14177.68 (11)
C2—C1—C9—C81.45 (12)C12—C11—C19—C141.07 (13)
C9—C1—C11—C191.3 (2)C1—C11—C19—C182.1 (2)
C2—C1—C11—C19178.21 (11)C12—C11—C19—C18179.16 (12)
C9—C1—C11—C12179.87 (10)
 

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