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All molecule of the title compound, C16H18, centrosymmetric.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805036706/bt6776sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805036706/bt6776Isup2.hkl
Contains datablock I

CCDC reference: 293833

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.048
  • wR factor = 0.143
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.00 Sigma PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 2003); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Version 2.1; Bergerhoff et al., 1997); software used to prepare material for publication: SHELXL97.

1,4-diphenylbutane top
Crystal data top
C16H18F(000) = 228
Mr = 210.30Dx = 1.090 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.787 (1) ÅCell parameters from 12888 reflections
b = 8.776 (2) Åθ = 26.6–1288°
c = 12.617 (3) ŵ = 0.06 mm1
β = 91.25 (3)°T = 293 K
V = 640.6 (2) Å3Prism, colourless
Z = 20.10 × 0.06 × 0.05 mm
Data collection top
Nonius KappaCCD
diffractometer
1464 independent reflections
Radiation source: fine-focus sealed tube1139 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 3.5°
φ and ω scansh = 77
Absorption correction: multi-scan
(DENZO; Otwinowski & Minor, 1997
k = 1111
Tmin = 0.994, Tmax = 0.997l = 1616
2835 measured 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)] = 0.048All H-atom parameters refined
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.0749P)2 + 0.0552P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.002
1464 reflectionsΔρmax = 0.11 e Å3
110 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.09 (3)
Special details top

Experimental. Single-crystal X-ray intensity data were collected at 293 K on a Nonius Kappa diffractometer with CCD-area detector, using 805 frames with phi- and omega-increments of 1.5 degrees and a counting time of 12 s per frame. The crystal- to-detector-distance was 34 mm. The whole ewald sphere was measured. The reflection data were processed with the Nonius program suite DENZO-SMN and corrected for Lorentz, polarization, background and absorption effects (Otwinowski and Minor, 1997). The crystal structure was determined by Direct methods (SHELXS97, Sheldrick, 1997) and subsequent Fourier and difference Fourier syntheses, followed by full-matrix least-squares refinements on F2 (SHELXL97, Sheldrick, 1997). All hydrogen atoms were refined freely. Using anisotropic treatment of the non-H atoms and unrestrained isotropic treatment of the H atoms, the refinement converged at R-values of 0.048.

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
C60.8581 (2)0.15225 (13)0.71853 (9)0.0549 (4)
C10.8987 (3)0.07511 (16)0.81254 (11)0.0684 (4)
H11.031 (2)0.0078 (19)0.8194 (12)0.090 (5)*
C20.7520 (3)0.09114 (18)0.89703 (11)0.0756 (5)
H20.779 (3)0.034 (2)0.9597 (15)0.106 (5)*
C30.5644 (2)0.18631 (19)0.88904 (11)0.0740 (5)
H30.462 (3)0.1975 (19)0.9495 (15)0.092 (5)*
C40.5228 (3)0.26404 (19)0.79690 (11)0.0750 (5)
H40.392 (3)0.3338 (19)0.7899 (14)0.099 (5)*
C50.6680 (2)0.24721 (16)0.71236 (10)0.0646 (4)
H50.638 (3)0.3045 (19)0.6465 (14)0.093 (5)*
C71.0116 (3)0.13128 (18)0.62438 (11)0.0680 (4)
H711.026 (3)0.2277 (19)0.5840 (13)0.090 (5)*
H721.167 (3)0.1023 (19)0.6482 (13)0.089 (5)*
C80.9273 (2)0.00660 (14)0.54925 (9)0.0583 (4)
H811.073 (2)0.0921 (19)0.4129 (12)0.079 (4)*
H820.766 (2)0.0285 (16)0.5264 (11)0.074 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C60.0580 (7)0.0564 (7)0.0506 (6)0.0090 (5)0.0088 (5)0.0109 (5)
C10.0741 (8)0.0664 (8)0.0647 (8)0.0096 (7)0.0042 (6)0.0030 (6)
C20.0962 (11)0.0808 (10)0.0499 (7)0.0001 (8)0.0067 (7)0.0056 (6)
C30.0746 (9)0.0950 (10)0.0531 (7)0.0032 (8)0.0170 (6)0.0123 (6)
C40.0647 (8)0.0952 (11)0.0653 (8)0.0149 (7)0.0071 (6)0.0113 (7)
C50.0688 (8)0.0740 (8)0.0512 (7)0.0029 (6)0.0042 (5)0.0005 (6)
C70.0673 (8)0.0740 (9)0.0635 (8)0.0144 (7)0.0217 (6)0.0172 (6)
C80.0629 (8)0.0590 (8)0.0539 (7)0.0077 (6)0.0188 (5)0.0073 (5)
Geometric parameters (Å, º) top
C6—C51.3810 (19)C4—C51.3799 (19)
C6—C11.3814 (19)C4—H40.978 (17)
C6—C71.5099 (16)C5—H50.983 (18)
C1—C21.384 (2)C7—C81.5211 (17)
C1—H10.968 (16)C7—H710.992 (17)
C2—C31.372 (2)C7—H720.977 (16)
C2—H20.946 (19)C8—C8i1.520 (2)
C3—C41.365 (2)C8—H820.991 (14)
C3—H30.981 (18)
C5—C6—C1117.67 (12)C5—C4—H4118.8 (11)
C5—C6—C7120.72 (12)C4—C5—C6121.24 (13)
C1—C6—C7121.60 (13)C4—C5—H5119.8 (10)
C6—C1—C2121.06 (13)C6—C5—H5118.9 (10)
C6—C1—H1119.7 (9)C6—C7—C8113.07 (10)
C2—C1—H1119.2 (9)C6—C7—H71111.0 (10)
C3—C2—C1120.19 (13)C8—C7—H71108.8 (10)
C3—C2—H2120.0 (11)C6—C7—H72110.1 (10)
C1—C2—H2119.8 (11)C8—C7—H72106.6 (10)
C4—C3—C2119.45 (13)H71—C7—H72107.0 (14)
C4—C3—H3120.9 (10)C8i—C8—C7112.86 (12)
C2—C3—H3119.6 (10)C8i—C8—H82108.2 (8)
C3—C4—C5120.39 (14)C7—C8—H82109.2 (8)
C3—C4—H4120.8 (11)
Symmetry code: (i) x+2, y, z+1.
 

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