[Tris(4-tolyl)­methyl]­benzene

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.

Computing details

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

Crystal data

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) Å^3	Needle, colourless
Z = 8	0.6 × 0.4 × 0.36 mm
F(000) = 1552

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.173	w = 1/[σ^2(Fo^2) + (0.0705P)^2 + 1.0945P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0007 (3)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)