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In the investigated crystal of the title compound, C18H16, the unit cell contains two centrosymmetric and nearly planar mol­ecules [maximum deviation from planarity 0.0401 (10) Å]. The length of the central double bond is 1.322 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018311/cf6120sup1.cif
Contains datablocks I, ccd1600

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018311/cf6120Isup2.hkl
Contains datablock I

CCDC reference: 177192

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.101
  • Data-to-parameter ratio = 17.5

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 (Otwinowski & Minor, 1997); 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), PLATON (Spek, 2001).

(I) top
Crystal data top
C18H16F(000) = 248
Mr = 232.31Dx = 1.224 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.5489 (2) ÅCell parameters from 5614 reflections
b = 4.8968 (2) Åθ = 4.8–27.5°
c = 17.0874 (6) ŵ = 0.07 mm1
β = 93.8964 (19)°T = 291 K
V = 630.18 (4) Å3Needle, colourless
Z = 20.3 × 0.07 × 0.07 mm
Data collection top
Nonius KappaCCD
diffractometer
896 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 27.5°, θmin = 4.8°
Detector resolution: 19 vertical, 18 horizontal pixels mm-1h = 99
284 frames via ω–rotation (Δω=1°) with three sets at different κ–angles and two times 100 s per frame scansk = 66
5614 measured reflectionsl = 2222
1439 independent reflections
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 0.90 w = 1/[σ2(Fo2) + (0.0609P)2]
where P = (Fo2 + 2Fc2)/3
1439 reflections(Δ/σ)max < 0.001
82 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.13 e Å3
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
C10.04106 (14)0.2312 (2)0.41503 (6)0.0462 (3)
H1A0.11550.09740.43880.055*
H1B0.11250.33220.37560.055*
C20.04381 (13)0.4218 (2)0.47638 (6)0.0400 (3)
C30.24464 (13)0.4048 (2)0.47513 (6)0.0444 (3)
H3A0.29430.57920.46100.053*
H3B0.29810.34940.52590.053*
C40.27381 (14)0.1926 (2)0.41388 (6)0.0420 (3)
C50.43312 (16)0.0915 (2)0.38983 (7)0.0533 (3)
H50.54060.15610.41250.064*
C60.43056 (17)0.1065 (3)0.33175 (7)0.0578 (4)
H60.53680.17520.31540.069*
C70.27106 (17)0.2021 (3)0.29802 (7)0.0581 (4)
H70.27060.33500.25910.070*
C80.11215 (16)0.1020 (2)0.32161 (6)0.0513 (3)
H80.00500.16660.29870.062*
C90.11386 (14)0.0955 (2)0.37976 (6)0.0417 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0433 (6)0.0463 (7)0.0485 (6)0.0002 (5)0.0003 (5)0.0018 (5)
C20.0417 (6)0.0376 (6)0.0407 (6)0.0013 (4)0.0024 (4)0.0027 (5)
C30.0416 (7)0.0429 (7)0.0486 (6)0.0022 (5)0.0019 (5)0.0006 (5)
C40.0428 (7)0.0383 (6)0.0455 (6)0.0001 (5)0.0069 (5)0.0033 (5)
C50.0462 (7)0.0513 (7)0.0636 (7)0.0026 (5)0.0121 (6)0.0008 (6)
C60.0595 (8)0.0546 (8)0.0618 (8)0.0079 (6)0.0237 (7)0.0007 (6)
C70.0743 (10)0.0530 (8)0.0479 (7)0.0067 (6)0.0108 (7)0.0054 (6)
C80.0576 (8)0.0497 (8)0.0460 (6)0.0013 (5)0.0015 (6)0.0036 (6)
C90.0454 (6)0.0394 (6)0.0405 (6)0.0018 (5)0.0034 (5)0.0025 (5)
Geometric parameters (Å, º) top
C1—C91.5060 (15)C4—C91.3886 (15)
C1—C21.5129 (16)C5—C61.3867 (16)
C1—H1A0.970C5—H50.930
C1—H1B0.970C6—C71.3808 (17)
C2—C2i1.322 (2)C6—H60.930
C2—C31.5199 (14)C7—C81.3810 (15)
C3—C41.5016 (15)C7—H70.930
C3—H3A0.970C8—C91.3862 (16)
C3—H3B0.970C8—H80.930
C4—C51.3883 (15)
C9—C1—C2104.22 (9)C9—C4—C3111.41 (9)
C9—C1—H1A110.9C6—C5—C4119.39 (11)
C2—C1—H1A110.9C6—C5—H5120.3
C9—C1—H1B110.9C4—C5—H5120.3
C2—C1—H1B110.9C7—C6—C5120.34 (11)
H1A—C1—H1B108.9C7—C6—H6119.8
C2i—C2—C1125.06 (12)C5—C6—H6119.8
C2i—C2—C3125.53 (12)C6—C7—C8120.53 (12)
C1—C2—C3109.41 (9)C6—C7—H7119.7
C4—C3—C2103.97 (8)C8—C7—H7119.7
C4—C3—H3A111.0C7—C8—C9119.40 (11)
C2—C3—H3A111.0C7—C8—H8120.3
C4—C3—H3B111.0C9—C8—H8120.3
C2—C3—H3B111.0C8—C9—C4120.35 (10)
H3A—C3—H3B109.0C8—C9—C1128.69 (10)
C5—C4—C9119.99 (11)C4—C9—C1110.96 (10)
C5—C4—C3128.61 (10)
C9—C1—C2—C2i178.14 (14)C6—C7—C8—C90.15 (19)
C9—C1—C2—C31.83 (11)C7—C8—C9—C40.17 (18)
C2i—C2—C3—C4177.91 (14)C7—C8—C9—C1179.38 (11)
C1—C2—C3—C42.07 (11)C5—C4—C9—C80.06 (17)
C2—C3—C4—C5178.46 (11)C3—C4—C9—C8179.94 (10)
C2—C3—C4—C91.54 (12)C5—C4—C9—C1179.57 (9)
C9—C4—C5—C60.08 (17)C3—C4—C9—C10.44 (13)
C3—C4—C5—C6179.92 (11)C2—C1—C9—C8178.71 (11)
C4—C5—C6—C70.10 (18)C2—C1—C9—C40.88 (12)
C5—C6—C7—C80.02 (19)
Symmetry code: (i) x, y+1, z+1.
 

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