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The crystal structure of the title compound, C28H26, in the monoclinic space group C2/c has a columnar packing arrangement with a 7.20 Å axis, a feature common to several tetraphenylmethanes.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006090/qa0285sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006090/qa0285Isup2.hkl |
CCDC reference: 146096
Computing details top
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: Xtal3.5 (Hall et al., 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
tris-(4-Tolyl)phenylmethane top
Crystal data top
| C28H26 | Dx = 1.135 Mg m−3 |
| Mr = 362.49 | Melting point: 552 K K |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 17.843 (4) Å | Cell parameters from 25 reflections |
| b = 7.2015 (14) Å | θ = 1.5–27.5° |
| c = 33.176 (7) Å | µ = 0.06 mm−1 |
| β = 95.59 (3)° | T = 293 K |
| V = 4242.6 (15) Å3 | Needle, colourless |
| Z = 8 | 0.6 × 0.4 × 0.36 mm |
| F(000) = 1552 |
Data collection top
| Enraf-Nonius CAD-4 diffractometer | θmax = 27.5°, θmin = 2.3° |
| ω scans | h = −23→23 |
| 9332 measured reflections | k = −9→0 |
| 4864 independent reflections | l = −42→43 |
| 3098 reflections with I > 2σ(I) | 3 standard reflections every 100 reflections |
| Rint = 0.019 | intensity decay: none |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
| wR(F2) = 0.173 | w = 1/[σ2(Fo2) + (0.0705P)2 + 1.0945P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.15 | (Δ/σ)max < 0.001 |
| 4864 reflections | Δρmax = 0.20 e Å−3 |
| 254 parameters | Δρmin = −0.15 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0007 (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 | 0.22663 (9) | 0.1089 (2) | 0.11482 (5) | 0.0396 (4) | |
| C2 | 0.26932 (10) | 0.2376 (3) | 0.14675 (5) | 0.0410 (4) | |
| C3 | 0.31078 (10) | 0.3850 (3) | 0.13363 (6) | 0.0466 (4) | |
| H3A | 0.3124 | 0.4030 | 0.1060 | 0.056* | |
| C4 | 0.34960 (10) | 0.5053 (3) | 0.16032 (6) | 0.0508 (5) | |
| H4A | 0.3770 | 0.6019 | 0.1503 | 0.061* | |
| C5 | 0.34849 (12) | 0.4849 (3) | 0.20180 (6) | 0.0571 (5) | |
| C6 | 0.30719 (13) | 0.3392 (3) | 0.21488 (6) | 0.0642 (6) | |
| H6A | 0.3053 | 0.3222 | 0.2425 | 0.077* | |
| C7 | 0.26835 (12) | 0.2172 (3) | 0.18813 (6) | 0.0523 (5) | |
| H7A | 0.2412 | 0.1201 | 0.1982 | 0.063* | |
| C8 | 0.38940 (16) | 0.6203 (4) | 0.23101 (8) | 0.0943 (9) | |
| H8A | 0.3826 | 0.5845 | 0.2583 | 0.142* | |
| H8B | 0.3695 | 0.7429 | 0.2259 | 0.142* | |
| H8C | 0.4421 | 0.6196 | 0.2273 | 0.142* | |
| C9 | 0.17197 (10) | −0.0209 (2) | 0.13484 (5) | 0.0411 (4) | |
| C10 | 0.20125 (11) | −0.1697 (3) | 0.15813 (5) | 0.0463 (5) | |
| H10A | 0.2531 | −0.1883 | 0.1611 | 0.056* | |
| C11 | 0.15583 (12) | −0.2899 (3) | 0.17683 (6) | 0.0522 (5) | |
| H11A | 0.1777 | −0.3869 | 0.1923 | 0.063* | |
| C12 | 0.07833 (13) | −0.2701 (3) | 0.17315 (6) | 0.0580 (5) | |
| C13 | 0.04916 (12) | −0.1235 (3) | 0.14997 (7) | 0.0636 (6) | |
| H13A | −0.0027 | −0.1063 | 0.1468 | 0.076* | |
| C14 | 0.09446 (11) | −0.0011 (3) | 0.13120 (6) | 0.0530 (5) | |
| H14A | 0.0724 | 0.0962 | 0.1159 | 0.064* | |
| C15 | 0.02844 (16) | −0.4037 (4) | 0.19316 (9) | 0.0930 (9) | |
| H15A | −0.0233 | −0.3678 | 0.1872 | 0.140* | |
| H15B | 0.0413 | −0.4015 | 0.2219 | 0.140* | |
| H15C | 0.0355 | −0.5268 | 0.1831 | 0.140* | |
| C16 | 0.28245 (9) | −0.0183 (2) | 0.09485 (5) | 0.0396 (4) | |
| C17 | 0.25489 (11) | −0.1614 (3) | 0.06934 (5) | 0.0462 (4) | |
| H17A | 0.2031 | −0.1755 | 0.0639 | 0.055* | |
| C18 | 0.30207 (11) | −0.2826 (3) | 0.05194 (6) | 0.0496 (5) | |
| H18A | 0.2815 | −0.3754 | 0.0348 | 0.060* | |
| C19 | 0.37964 (11) | −0.2686 (3) | 0.05962 (6) | 0.0494 (5) | |
| C20 | 0.40728 (11) | −0.1276 (3) | 0.08489 (6) | 0.0529 (5) | |
| H20A | 0.4591 | −0.1149 | 0.0906 | 0.063* | |
| C21 | 0.36010 (10) | −0.0042 (3) | 0.10210 (6) | 0.0474 (5) | |
| H21A | 0.3809 | 0.0899 | 0.1188 | 0.057* | |
| C22 | 0.43148 (13) | −0.4037 (3) | 0.04155 (7) | 0.0704 (6) | |
| H22A | 0.4828 | −0.3722 | 0.0502 | 0.106* | |
| H22B | 0.4235 | −0.3977 | 0.0125 | 0.106* | |
| H22C | 0.4212 | −0.5272 | 0.0504 | 0.106* | |
| C23 | 0.18313 (9) | 0.2378 (2) | 0.08326 (5) | 0.0410 (4) | |
| C24 | 0.14130 (10) | 0.3841 (3) | 0.09727 (6) | 0.0489 (5) | |
| H24A | 0.1404 | 0.4006 | 0.1250 | 0.059* | |
| C25 | 0.10141 (11) | 0.5046 (3) | 0.07104 (7) | 0.0564 (5) | |
| H25A | 0.0737 | 0.6003 | 0.0812 | 0.068* | |
| C26 | 0.10232 (12) | 0.4840 (3) | 0.02989 (7) | 0.0628 (6) | |
| H26A | 0.0751 | 0.5647 | 0.0121 | 0.075* | |
| C27 | 0.14388 (12) | 0.3429 (3) | 0.01539 (6) | 0.0625 (6) | |
| H27A | 0.1453 | 0.3287 | −0.0124 | 0.075* | |
| C28 | 0.18381 (11) | 0.2212 (3) | 0.04189 (6) | 0.0514 (5) | |
| H28A | 0.2116 | 0.1263 | 0.0315 | 0.062* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0366 (8) | 0.0446 (9) | 0.0377 (8) | −0.0010 (8) | 0.0042 (7) | 0.0017 (8) |
| C2 | 0.0380 (9) | 0.0454 (10) | 0.0394 (9) | 0.0040 (8) | 0.0025 (7) | −0.0013 (8) |
| C3 | 0.0450 (10) | 0.0501 (11) | 0.0446 (10) | −0.0008 (9) | 0.0037 (8) | 0.0005 (8) |
| C4 | 0.0401 (10) | 0.0462 (10) | 0.0654 (13) | −0.0002 (8) | 0.0018 (9) | −0.0028 (9) |
| C5 | 0.0512 (12) | 0.0607 (13) | 0.0568 (12) | 0.0011 (10) | −0.0074 (9) | −0.0094 (10) |
| C6 | 0.0733 (15) | 0.0758 (15) | 0.0414 (11) | −0.0066 (13) | −0.0053 (10) | −0.0040 (10) |
| C7 | 0.0594 (12) | 0.0550 (12) | 0.0420 (10) | −0.0076 (10) | 0.0034 (9) | 0.0034 (9) |
| C8 | 0.0895 (19) | 0.102 (2) | 0.0867 (19) | −0.0257 (17) | −0.0159 (15) | −0.0253 (17) |
| C9 | 0.0406 (9) | 0.0450 (10) | 0.0382 (9) | 0.0000 (8) | 0.0070 (7) | −0.0030 (8) |
| C10 | 0.0437 (10) | 0.0481 (11) | 0.0476 (10) | 0.0033 (8) | 0.0070 (8) | 0.0003 (9) |
| C11 | 0.0650 (13) | 0.0488 (11) | 0.0435 (10) | −0.0027 (10) | 0.0090 (9) | 0.0013 (9) |
| C12 | 0.0608 (13) | 0.0646 (13) | 0.0511 (11) | −0.0110 (11) | 0.0174 (10) | 0.0031 (10) |
| C13 | 0.0439 (11) | 0.0783 (16) | 0.0704 (14) | −0.0008 (11) | 0.0150 (10) | 0.0065 (12) |
| C14 | 0.0407 (10) | 0.0593 (12) | 0.0595 (12) | 0.0029 (9) | 0.0072 (8) | 0.0066 (10) |
| C15 | 0.0853 (18) | 0.107 (2) | 0.0908 (19) | −0.0271 (17) | 0.0270 (15) | 0.0243 (17) |
| C16 | 0.0394 (9) | 0.0439 (10) | 0.0359 (9) | 0.0000 (8) | 0.0056 (7) | 0.0031 (7) |
| C17 | 0.0419 (10) | 0.0505 (11) | 0.0464 (10) | −0.0035 (8) | 0.0046 (8) | −0.0001 (9) |
| C18 | 0.0578 (12) | 0.0463 (11) | 0.0450 (10) | −0.0013 (9) | 0.0063 (9) | −0.0040 (9) |
| C19 | 0.0542 (11) | 0.0477 (11) | 0.0476 (10) | 0.0053 (9) | 0.0126 (9) | 0.0052 (9) |
| C20 | 0.0393 (10) | 0.0598 (12) | 0.0603 (12) | 0.0031 (9) | 0.0083 (9) | 0.0002 (10) |
| C21 | 0.0431 (10) | 0.0495 (11) | 0.0495 (10) | −0.0029 (9) | 0.0043 (8) | −0.0041 (9) |
| C22 | 0.0708 (15) | 0.0666 (14) | 0.0760 (15) | 0.0173 (12) | 0.0182 (12) | −0.0060 (12) |
| C23 | 0.0370 (9) | 0.0439 (10) | 0.0419 (9) | −0.0039 (8) | 0.0024 (7) | 0.0018 (8) |
| C24 | 0.0471 (11) | 0.0480 (11) | 0.0512 (11) | −0.0021 (9) | 0.0027 (8) | −0.0015 (9) |
| C25 | 0.0461 (11) | 0.0475 (11) | 0.0750 (14) | 0.0013 (9) | 0.0032 (10) | 0.0087 (10) |
| C26 | 0.0535 (12) | 0.0646 (14) | 0.0682 (14) | −0.0006 (11) | −0.0040 (10) | 0.0228 (12) |
| C27 | 0.0643 (13) | 0.0763 (15) | 0.0457 (11) | −0.0040 (12) | −0.0010 (10) | 0.0146 (11) |
| C28 | 0.0520 (11) | 0.0581 (12) | 0.0441 (10) | 0.0002 (9) | 0.0045 (8) | 0.0031 (9) |
Geometric parameters (Å, º) top
| C1—C9 | 1.546 (2) | C12—C15 | 1.508 (3) |
| C1—C16 | 1.549 (2) | C13—C14 | 1.384 (3) |
| C1—C23 | 1.550 (2) | C16—C21 | 1.387 (2) |
| C1—C2 | 1.551 (2) | C16—C17 | 1.392 (2) |
| C2—C7 | 1.382 (2) | C17—C18 | 1.378 (3) |
| C2—C3 | 1.388 (3) | C18—C19 | 1.386 (3) |
| C3—C4 | 1.377 (3) | C19—C20 | 1.377 (3) |
| C4—C5 | 1.386 (3) | C19—C22 | 1.506 (3) |
| C5—C6 | 1.376 (3) | C20—C21 | 1.385 (3) |
| C5—C8 | 1.512 (3) | C23—C28 | 1.379 (2) |
| C6—C7 | 1.386 (3) | C23—C24 | 1.397 (3) |
| C9—C14 | 1.384 (2) | C24—C25 | 1.377 (3) |
| C9—C10 | 1.393 (3) | C25—C26 | 1.375 (3) |
| C10—C11 | 1.374 (3) | C26—C27 | 1.373 (3) |
| C11—C12 | 1.384 (3) | C27—C28 | 1.388 (3) |
| C12—C13 | 1.378 (3) | ||
| C9—C1—C16 | 106.58 (14) | C13—C12—C15 | 121.8 (2) |
| C9—C1—C23 | 110.90 (13) | C11—C12—C15 | 121.5 (2) |
| C16—C1—C23 | 111.47 (13) | C12—C13—C14 | 122.3 (2) |
| C9—C1—C2 | 110.87 (14) | C9—C14—C13 | 121.16 (19) |
| C16—C1—C2 | 110.61 (13) | C21—C16—C17 | 116.57 (16) |
| C23—C1—C2 | 106.48 (14) | C21—C16—C1 | 123.79 (16) |
| C7—C2—C3 | 116.83 (17) | C17—C16—C1 | 119.59 (15) |
| C7—C2—C1 | 124.19 (16) | C18—C17—C16 | 121.97 (17) |
| C3—C2—C1 | 118.98 (15) | C17—C18—C19 | 121.11 (18) |
| C4—C3—C2 | 122.00 (18) | C20—C19—C18 | 117.22 (18) |
| C3—C4—C5 | 121.13 (19) | C20—C19—C22 | 121.39 (19) |
| C6—C5—C4 | 116.98 (18) | C18—C19—C22 | 121.38 (19) |
| C6—C5—C8 | 122.0 (2) | C19—C20—C21 | 121.88 (18) |
| C4—C5—C8 | 121.0 (2) | C20—C21—C16 | 121.25 (18) |
| C5—C6—C7 | 122.08 (19) | C28—C23—C24 | 116.96 (17) |
| C2—C7—C6 | 120.97 (19) | C28—C23—C1 | 124.61 (16) |
| C14—C9—C10 | 116.44 (17) | C24—C23—C1 | 118.42 (15) |
| C14—C9—C1 | 124.55 (16) | C25—C24—C23 | 121.69 (19) |
| C10—C9—C1 | 119.01 (15) | C26—C25—C24 | 120.3 (2) |
| C11—C10—C9 | 121.96 (18) | C27—C26—C25 | 119.1 (2) |
| C10—C11—C12 | 121.54 (19) | C26—C27—C28 | 120.5 (2) |
| C13—C12—C11 | 116.64 (18) | C23—C28—C27 | 121.5 (2) |
