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Molecules of the title compound, C22H22, crystallize in space group P21/c and are located on crystallographic inversion centers. The structure reveals a twisted mol­ecule with a dihedral angle of 31.9 (2)° between the central and outer benzene rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021282/ac6115sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021282/ac6115Isup2.hkl
Contains datablock I

CCDC reference: 252971

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.047
  • wR factor = 0.177
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.743 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.18 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXL97.

3,3',5,5'-tetramethylterphenyl top
Crystal data top
C22H22F(000) = 308
Mr = 286.42Dx = 1.178 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.9264 (13) ÅCell parameters from 4518 reflections
b = 9.2297 (10) Åθ = 2.2–27.6°
c = 7.6075 (8) ŵ = 0.07 mm1
β = 105.381 (2)°T = 153 K
V = 807.42 (15) Å3Prism, colourless
Z = 20.4 × 0.1 × 0.09 mm
Data collection top
Bruker SMART APEX
diffractometer
1574 reflections with I > 2σ(I)
Radiation source: Sealed X-ray source, Mo Fine Focus Sealed TubeRint = 0.073
Graphite monochromatorθmax = 27.6°, θmin = 1.8°
φ and ω scansh = 1515
7844 measured reflectionsk = 1112
1854 independent reflectionsl = 99
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H-atom parameters constrained
S = 0.74 w = 1/[σ2(Fo2) + (0.2P)2]
where P = (Fo2 + 2Fc2)/3
1854 reflections(Δ/σ)max < 0.001
102 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.16 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
C10.82181 (10)0.02648 (11)0.19561 (15)0.0227 (3)
C20.71838 (9)0.09919 (12)0.11479 (15)0.0258 (3)
H20.70920.14510.00010.031*
C30.62783 (10)0.10549 (12)0.20013 (16)0.0273 (3)
C40.64374 (10)0.03779 (12)0.36792 (15)0.0268 (3)
H40.58270.04120.42650.032*
C50.74577 (10)0.03483 (12)0.45331 (14)0.0247 (3)
C60.83499 (9)0.03869 (12)0.36554 (15)0.0238 (3)
H60.90580.08650.42260.029*
C70.91431 (9)0.01446 (11)0.09792 (14)0.0224 (3)
C80.98528 (9)0.10877 (12)0.11664 (14)0.0242 (3)
H80.97600.18410.19680.029*
C90.93132 (9)0.12317 (12)0.02080 (14)0.0242 (3)
H90.88490.20830.03600.029*
C100.51516 (11)0.18216 (15)0.11082 (18)0.0362 (4)
H10A0.45100.13480.14640.054*
H10B0.50100.17780.02200.054*
H10C0.52040.28360.15010.054*
C110.75836 (11)0.11035 (14)0.63288 (17)0.0334 (3)
H11A0.70870.06270.69950.050*
H11B0.83960.10550.70510.050*
H11C0.73500.21200.61100.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0253 (6)0.0212 (5)0.0236 (6)0.0028 (4)0.0100 (4)0.0029 (4)
C20.0287 (6)0.0265 (6)0.0243 (6)0.0014 (4)0.0109 (5)0.0020 (4)
C30.0271 (6)0.0259 (6)0.0306 (7)0.0011 (4)0.0107 (5)0.0007 (4)
C40.0285 (6)0.0256 (6)0.0305 (6)0.0023 (4)0.0154 (5)0.0026 (4)
C50.0294 (6)0.0239 (6)0.0232 (6)0.0039 (4)0.0111 (4)0.0027 (4)
C60.0251 (6)0.0238 (6)0.0235 (6)0.0008 (4)0.0084 (4)0.0016 (4)
C70.0238 (6)0.0234 (6)0.0211 (6)0.0019 (4)0.0078 (4)0.0010 (4)
C80.0281 (6)0.0225 (6)0.0240 (6)0.0012 (4)0.0103 (5)0.0026 (4)
C90.0273 (6)0.0221 (6)0.0248 (6)0.0012 (4)0.0095 (5)0.0007 (4)
C100.0314 (7)0.0420 (8)0.0380 (7)0.0091 (5)0.0140 (5)0.0100 (5)
C110.0343 (7)0.0407 (7)0.0284 (7)0.0004 (5)0.0139 (5)0.0048 (5)
Geometric parameters (Å, º) top
C1—C61.3964 (15)C7—C81.4023 (15)
C1—C21.3956 (15)C7—C91.4003 (15)
C1—C71.4888 (15)C8—C9i1.3868 (15)
C2—C31.4011 (15)C8—H80.9500
C2—H20.9500C9—C8i1.3869 (15)
C3—C41.3883 (16)C9—H90.9500
C3—C101.5113 (16)C10—H10A0.9800
C4—C51.3901 (16)C10—H10B0.9800
C4—H40.9500C10—H10C0.9800
C5—C61.3987 (14)C11—H11A0.9800
C5—C111.5053 (16)C11—H11B0.9800
C6—H60.9500C11—H11C0.9800
C2—C1—C6118.97 (10)C8—C7—C1121.13 (9)
C2—C1—C7120.08 (10)C9i—C8—C7121.48 (10)
C6—C1—C7120.91 (10)C9i—C8—H8119.3
C1—C2—C3121.04 (10)C7—C8—H8119.3
C1—C2—H2119.5C8i—C9—C7121.15 (10)
C3—C2—H2119.5C8i—C9—H9119.4
C4—C3—C2118.24 (10)C7—C9—H9119.4
C4—C3—C10120.83 (10)C3—C10—H10A109.5
C2—C3—C10120.92 (10)C3—C10—H10B109.5
C3—C4—C5122.41 (10)H10A—C10—H10B109.5
C3—C4—H4118.8C3—C10—H10C109.5
C5—C4—H4118.8H10A—C10—H10C109.5
C4—C5—C6118.14 (10)H10B—C10—H10C109.5
C4—C5—C11120.77 (10)C5—C11—H11A109.5
C6—C5—C11121.07 (10)C5—C11—H11B109.5
C1—C6—C5121.19 (10)H11A—C11—H11B109.5
C1—C6—H6119.4C5—C11—H11C109.5
C5—C6—H6119.4H11A—C11—H11C109.5
C9—C7—C8117.37 (10)H11B—C11—H11C109.5
C9—C7—C1121.46 (9)
C6—C1—C2—C31.00 (16)C4—C5—C6—C10.95 (16)
C7—C1—C2—C3176.73 (9)C11—C5—C6—C1177.49 (10)
C1—C2—C3—C40.21 (16)C6—C1—C7—C831.59 (15)
C1—C2—C3—C10178.97 (11)C2—C1—C7—C8146.10 (11)
C2—C3—C4—C50.23 (17)C6—C1—C7—C9150.61 (11)
C10—C3—C4—C5179.41 (11)C2—C1—C7—C931.70 (15)
C3—C4—C5—C60.13 (17)C9—C7—C8—C9i0.35 (17)
C3—C4—C5—C11178.31 (10)C1—C7—C8—C9i177.53 (9)
C2—C1—C6—C51.38 (16)C8—C7—C9—C8i0.35 (17)
C7—C1—C6—C5176.33 (9)C1—C7—C9—C8i177.53 (9)
Symmetry code: (i) x+2, y, z.
 

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