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
CCDC reference: 252971
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (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
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
C22H22 | F(000) = 308 |
Mr = 286.42 | Dx = 1.178 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9264 (13) Å | Cell parameters from 4518 reflections |
b = 9.2297 (10) Å | θ = 2.2–27.6° |
c = 7.6075 (8) Å | µ = 0.07 mm−1 |
β = 105.381 (2)° | T = 153 K |
V = 807.42 (15) Å3 | Prism, colourless |
Z = 2 | 0.4 × 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 Tube | Rint = 0.073 |
Graphite monochromator | θmax = 27.6°, θmin = 1.8° |
φ and ω scans | h = −15→15 |
7844 measured reflections | k = −11→12 |
1854 independent reflections | l = −9→9 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.177 | H-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 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.82181 (10) | 0.02648 (11) | 0.19561 (15) | 0.0227 (3) | |
C2 | 0.71838 (9) | 0.09919 (12) | 0.11479 (15) | 0.0258 (3) | |
H2 | 0.7092 | 0.1451 | 0.0001 | 0.031* | |
C3 | 0.62783 (10) | 0.10549 (12) | 0.20013 (16) | 0.0273 (3) | |
C4 | 0.64374 (10) | 0.03779 (12) | 0.36792 (15) | 0.0268 (3) | |
H4 | 0.5827 | 0.0412 | 0.4265 | 0.032* | |
C5 | 0.74577 (10) | −0.03483 (12) | 0.45331 (14) | 0.0247 (3) | |
C6 | 0.83499 (9) | −0.03869 (12) | 0.36554 (15) | 0.0238 (3) | |
H6 | 0.9058 | −0.0865 | 0.4226 | 0.029* | |
C7 | 0.91431 (9) | 0.01446 (11) | 0.09792 (14) | 0.0224 (3) | |
C8 | 0.98528 (9) | −0.10877 (12) | 0.11664 (14) | 0.0242 (3) | |
H8 | 0.9760 | −0.1841 | 0.1968 | 0.029* | |
C9 | 0.93132 (9) | 0.12317 (12) | −0.02080 (14) | 0.0242 (3) | |
H9 | 0.8849 | 0.2083 | −0.0360 | 0.029* | |
C10 | 0.51516 (11) | 0.18216 (15) | 0.11082 (18) | 0.0362 (4) | |
H10A | 0.4510 | 0.1348 | 0.1464 | 0.054* | |
H10B | 0.5010 | 0.1778 | −0.0220 | 0.054* | |
H10C | 0.5204 | 0.2836 | 0.1501 | 0.054* | |
C11 | 0.75836 (11) | −0.11035 (14) | 0.63288 (17) | 0.0334 (3) | |
H11A | 0.7087 | −0.0627 | 0.6995 | 0.050* | |
H11B | 0.8396 | −0.1055 | 0.7051 | 0.050* | |
H11C | 0.7350 | −0.2120 | 0.6110 | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0253 (6) | 0.0212 (5) | 0.0236 (6) | −0.0028 (4) | 0.0100 (4) | −0.0029 (4) |
C2 | 0.0287 (6) | 0.0265 (6) | 0.0243 (6) | 0.0014 (4) | 0.0109 (5) | 0.0020 (4) |
C3 | 0.0271 (6) | 0.0259 (6) | 0.0306 (7) | 0.0011 (4) | 0.0107 (5) | −0.0007 (4) |
C4 | 0.0285 (6) | 0.0256 (6) | 0.0305 (6) | −0.0023 (4) | 0.0154 (5) | −0.0026 (4) |
C5 | 0.0294 (6) | 0.0239 (6) | 0.0232 (6) | −0.0039 (4) | 0.0111 (4) | −0.0027 (4) |
C6 | 0.0251 (6) | 0.0238 (6) | 0.0235 (6) | −0.0008 (4) | 0.0084 (4) | −0.0016 (4) |
C7 | 0.0238 (6) | 0.0234 (6) | 0.0211 (6) | −0.0019 (4) | 0.0078 (4) | −0.0010 (4) |
C8 | 0.0281 (6) | 0.0225 (6) | 0.0240 (6) | −0.0012 (4) | 0.0103 (5) | 0.0026 (4) |
C9 | 0.0273 (6) | 0.0221 (6) | 0.0248 (6) | 0.0012 (4) | 0.0095 (5) | 0.0007 (4) |
C10 | 0.0314 (7) | 0.0420 (8) | 0.0380 (7) | 0.0091 (5) | 0.0140 (5) | 0.0100 (5) |
C11 | 0.0343 (7) | 0.0407 (7) | 0.0284 (7) | 0.0004 (5) | 0.0139 (5) | 0.0048 (5) |
Geometric parameters (Å, º) top
C1—C6 | 1.3964 (15) | C7—C8 | 1.4023 (15) |
C1—C2 | 1.3956 (15) | C7—C9 | 1.4003 (15) |
C1—C7 | 1.4888 (15) | C8—C9i | 1.3868 (15) |
C2—C3 | 1.4011 (15) | C8—H8 | 0.9500 |
C2—H2 | 0.9500 | C9—C8i | 1.3869 (15) |
C3—C4 | 1.3883 (16) | C9—H9 | 0.9500 |
C3—C10 | 1.5113 (16) | C10—H10A | 0.9800 |
C4—C5 | 1.3901 (16) | C10—H10B | 0.9800 |
C4—H4 | 0.9500 | C10—H10C | 0.9800 |
C5—C6 | 1.3987 (14) | C11—H11A | 0.9800 |
C5—C11 | 1.5053 (16) | C11—H11B | 0.9800 |
C6—H6 | 0.9500 | C11—H11C | 0.9800 |
| | | |
C2—C1—C6 | 118.97 (10) | C8—C7—C1 | 121.13 (9) |
C2—C1—C7 | 120.08 (10) | C9i—C8—C7 | 121.48 (10) |
C6—C1—C7 | 120.91 (10) | C9i—C8—H8 | 119.3 |
C1—C2—C3 | 121.04 (10) | C7—C8—H8 | 119.3 |
C1—C2—H2 | 119.5 | C8i—C9—C7 | 121.15 (10) |
C3—C2—H2 | 119.5 | C8i—C9—H9 | 119.4 |
C4—C3—C2 | 118.24 (10) | C7—C9—H9 | 119.4 |
C4—C3—C10 | 120.83 (10) | C3—C10—H10A | 109.5 |
C2—C3—C10 | 120.92 (10) | C3—C10—H10B | 109.5 |
C3—C4—C5 | 122.41 (10) | H10A—C10—H10B | 109.5 |
C3—C4—H4 | 118.8 | C3—C10—H10C | 109.5 |
C5—C4—H4 | 118.8 | H10A—C10—H10C | 109.5 |
C4—C5—C6 | 118.14 (10) | H10B—C10—H10C | 109.5 |
C4—C5—C11 | 120.77 (10) | C5—C11—H11A | 109.5 |
C6—C5—C11 | 121.07 (10) | C5—C11—H11B | 109.5 |
C1—C6—C5 | 121.19 (10) | H11A—C11—H11B | 109.5 |
C1—C6—H6 | 119.4 | C5—C11—H11C | 109.5 |
C5—C6—H6 | 119.4 | H11A—C11—H11C | 109.5 |
C9—C7—C8 | 117.37 (10) | H11B—C11—H11C | 109.5 |
C9—C7—C1 | 121.46 (9) | | |
| | | |
C6—C1—C2—C3 | −1.00 (16) | C4—C5—C6—C1 | −0.95 (16) |
C7—C1—C2—C3 | 176.73 (9) | C11—C5—C6—C1 | 177.49 (10) |
C1—C2—C3—C4 | 0.21 (16) | C6—C1—C7—C8 | 31.59 (15) |
C1—C2—C3—C10 | −178.97 (11) | C2—C1—C7—C8 | −146.10 (11) |
C2—C3—C4—C5 | 0.23 (17) | C6—C1—C7—C9 | −150.61 (11) |
C10—C3—C4—C5 | 179.41 (11) | C2—C1—C7—C9 | 31.70 (15) |
C3—C4—C5—C6 | 0.13 (17) | C9—C7—C8—C9i | −0.35 (17) |
C3—C4—C5—C11 | −178.31 (10) | C1—C7—C8—C9i | 177.53 (9) |
C2—C1—C6—C5 | 1.38 (16) | C8—C7—C9—C8i | 0.35 (17) |
C7—C1—C6—C5 | −176.33 (9) | C1—C7—C9—C8i | −177.53 (9) |
Symmetry code: (i) −x+2, −y, −z. |