1,3,5-Tris(p-bromo­phenyl)­benzene

Beltran, L.M.C.; Cui, C.; Leung, D.H.; Xu, J.; Hollander, F.J.

doi:10.1107/S1600536802010401

1,3,5-Tris(p-bromophenyl)benzene

L. M. C. Beltran, C. Cui, D. H. Leung, J. Xu and F. J. Hollander

The title compound, C₂₄H₁₅Br₃, crystallizes in the orthorhombic space group P2₁2₁2₁ with three molecules in the asymmetric unit. The crystal was found to be inversion twinned and the appropriate twin law was applied, resulting in R₁ = 0.035 for the experimental data measured at T = 136 K.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010401/cv6114sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010401/cv6114Isup2.hkl Contains datablock I

CCDC reference: 189912

checkCIF report

Key indicators

Single-crystal X-ray study
T = 136 K
Mean (C-C) = 0.011 Å
R factor = 0.035
wR factor = 0.070
Data-to-parameter ratio = 13.3

checkCIF results

No syntax errors found


 Alert Level A:



PLAT_213  Alert A Atom C24     has ADP max/min Ratio ...........       5.60 prolate

Author response: The elongated thermal ellipsoid on atom C24 was noted. Given the face-centered indexed correction, we are uncertain as to why this atom has such a disparate thermal parameter ratio.


 Alert Level B:



PLAT_111  Alert B ADDSYM detects (pseudo) centre of symmetry ...         80 Perc Fit

Author response: This crystal was found to be inversion twinned.


 Alert Level C:



GOODF_01  Alert C The least squares goodness of fit parameter lies
          outside the range 0.80 <> 2.00
          Goodness of fit given =      0.742

THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5875

PLAT_213  Alert C Atom C15     has ADP max/min Ratio ...........       3.60 oblate

PLAT_213  Alert C Atom C34     has ADP max/min Ratio ...........       3.40 oblate

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.68
         From the CIF: _reflns_number_total               9744
         Count of symmetry unique reflns         5609
         Completeness (_total/calc)            173.72%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      4135
         Fraction of Friedel pairs measured     0.737
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 1 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 4 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: XS in SHELXTL (Bruker, 2001); program(s) used to refine structure: XL in SHELXTL; molecular graphics: SHELXTL.

(I) top

Crystal data top

C₂₄H₁₅Br₃	D_x = 1.807 Mg m⁻³
M_r = 543.09	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 6200 reflections
a = 14.4165 (3) Å	θ = 1.8–24.8°
b = 18.9655 (4) Å	µ = 6.07 mm⁻¹
c = 21.9088 (2) Å	T = 136 K
V = 5990.22 (19) Å³	Parallelepiped, colorless
Z = 12	0.37 × 0.17 × 0.07 mm
F(000) = 3168

Data collection top

Siemens SMART CCD diffractometer	9744 independent reflections
Radiation source: fine-focus sealed tube	6390 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ω scans	θ_max = 24.7°, θ_min = 1.8°
Absorption correction: analytical (XPREP; Blessing, 1995)	h = −10→16
T_min = 0.212, T_max = 0.669	k = −20→22
26670 measured reflections	l = −25→25

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.02P)²] where P = (F_o² + 2F_c²)/3
S = 0.74	(Δ/σ)_max = 0.029
9744 reflections	Δρ_max = 0.42 e Å⁻³
731 parameters	Δρ_min = −0.56 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 4135 Friedel pairs [Please check]
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (3)

Special details top

Experimental. 52% Inversion Twinned Crystal [-1 0 0 0 - 1 0 0 0 - 1] Face Indexed Absorption Correction Applied

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	U_iso*/U_eq
Br1	0.45167 (6)	0.10847 (5)	−0.05064 (4)	0.0422 (3)
Br2	0.48216 (7)	0.06305 (5)	0.55170 (4)	0.0406 (3)
Br3	0.96738 (6)	0.53996 (4)	0.26551 (4)	0.0235 (2)
Br4	0.17547 (6)	0.07565 (5)	−0.06665 (4)	0.0309 (2)
Br5	0.10990 (6)	0.10842 (5)	0.54198 (4)	0.0369 (2)
Br6	0.64029 (6)	0.54175 (4)	0.23930 (4)	0.0254 (2)
Br7	−0.19597 (6)	0.06913 (5)	−0.03744 (4)	0.0388 (3)
Br8	−0.15706 (6)	0.08387 (4)	0.56348 (3)	0.0282 (2)
Br9	0.30216 (6)	0.55008 (4)	0.24342 (4)	0.0263 (2)
C11	0.5830 (6)	0.2172 (4)	0.2001 (3)	0.012 (2)
C12	0.5553 (5)	0.1864 (4)	0.2549 (4)	0.019 (2)
H12A	0.5071	0.1524	0.2546	0.022*
C13	0.5968 (6)	0.2044 (4)	0.3101 (4)	0.013 (2)
C14	0.6673 (5)	0.2548 (5)	0.3099 (4)	0.018 (2)
H14A	0.6989	0.2651	0.3469	0.021*
C15	0.6928 (5)	0.2906 (4)	0.2566 (4)	0.0131 (19)
C16	0.6494 (6)	0.2705 (4)	0.2023 (4)	0.018 (2)
H16A	0.6658	0.2940	0.1655	0.021*
C21	0.5458 (5)	0.1926 (4)	0.1407 (3)	0.0127 (19)
C22	0.5329 (5)	0.2377 (4)	0.0916 (3)	0.0170 (19)
H22A	0.5435	0.2868	0.0969	0.020*
C23	0.5048 (5)	0.2128 (4)	0.0348 (4)	0.025 (2)
H23A	0.4981	0.2441	0.0013	0.031*
C24	0.4870 (5)	0.1417 (4)	0.0279 (3)	0.020 (2)
C25	0.4971 (5)	0.0964 (4)	0.0759 (4)	0.023 (2)
H25A	0.4842	0.0477	0.0707	0.028*
C26	0.5262 (5)	0.1214 (4)	0.1321 (3)	0.023 (2)
H26A	0.5328	0.0895	0.1653	0.027*
C31	0.5683 (6)	0.1694 (4)	0.3681 (3)	0.014 (2)
C32	0.4752 (5)	0.1564 (4)	0.3816 (3)	0.0202 (19)
H32A	0.4289	0.1696	0.3529	0.024*
C33	0.4491 (5)	0.1253 (4)	0.4349 (3)	0.026 (2)
H33A	0.3855	0.1172	0.4438	0.031*
C34	0.5167 (6)	0.1060 (4)	0.4755 (3)	0.021 (2)
C35	0.6097 (5)	0.1165 (4)	0.4647 (3)	0.0225 (19)
H35A	0.6550	0.1023	0.4937	0.027*
C36	0.6355 (5)	0.1483 (4)	0.4104 (3)	0.0190 (19)
H36A	0.6993	0.1559	0.4018	0.023*
C41	0.7618 (5)	0.3481 (4)	0.2590 (4)	0.0137 (19)
C42	0.7803 (5)	0.3844 (4)	0.3128 (3)	0.018 (2)
H42A	0.7494	0.3702	0.3491	0.021*
C43	0.8420 (5)	0.4405 (4)	0.3158 (3)	0.018 (2)
H43A	0.8535	0.4642	0.3532	0.021*
C44	0.8867 (5)	0.4610 (4)	0.2622 (4)	0.0163 (19)
C45	0.8713 (6)	0.4257 (4)	0.2077 (3)	0.019 (2)
H45A	0.9018	0.4401	0.1714	0.023*
C46	0.8107 (6)	0.3691 (4)	0.2072 (3)	0.017 (2)
H46A	0.8021	0.3438	0.1702	0.021*
C51	0.2674 (6)	0.2108 (4)	0.1825 (4)	0.014 (2)
C52	0.2287 (5)	0.1872 (4)	0.2374 (4)	0.0142 (19)
H52A	0.1859	0.1490	0.2369	0.017*
C53	0.2521 (6)	0.2191 (4)	0.2934 (4)	0.015 (2)
C54	0.3164 (5)	0.2739 (4)	0.2936 (4)	0.015 (2)
H54A	0.3337	0.2951	0.3312	0.018*
C55	0.3558 (5)	0.2980 (4)	0.2391 (4)	0.0147 (19)
C56	0.3314 (6)	0.2656 (5)	0.1845 (4)	0.017 (2)
H56A	0.3591	0.2813	0.1476	0.021*
C61	0.2447 (6)	0.1773 (4)	0.1229 (4)	0.015 (2)
C62	0.2339 (5)	0.2201 (4)	0.0711 (4)	0.024 (2)
H62A	0.2399	0.2698	0.0745	0.029*
C63	0.2143 (5)	0.1895 (4)	0.0149 (4)	0.024 (2)
H63A	0.2078	0.2185	−0.0202	0.028*
C64	0.2042 (6)	0.1174 (4)	0.0096 (3)	0.019 (2)
C65	0.2148 (5)	0.0740 (4)	0.0610 (3)	0.0234 (19)
H65A	0.2091	0.0242	0.0580	0.028*
C66	0.2341 (5)	0.1068 (4)	0.1169 (3)	0.0193 (19)
H66A	0.2400	0.0781	0.1523	0.023*
C71	0.2135 (6)	0.1914 (4)	0.3521 (4)	0.013 (2)
C72	0.1875 (5)	0.1215 (4)	0.3605 (3)	0.0195 (19)
H72A	0.1903	0.0901	0.3267	0.023*
C73	0.1579 (5)	0.0962 (4)	0.4160 (3)	0.023 (2)
H73A	0.1434	0.0477	0.4209	0.028*
C74	0.1496 (5)	0.1424 (4)	0.4643 (3)	0.020 (2)
C75	0.1704 (5)	0.2126 (4)	0.4579 (4)	0.027 (2)
H75A	0.1633	0.2439	0.4914	0.033*
C76	0.2024 (5)	0.2379 (4)	0.4011 (3)	0.020 (2)
H76A	0.2165	0.2865	0.3962	0.024*
C81	0.4252 (5)	0.3569 (4)	0.2403 (4)	0.0141 (19)
C82	0.4772 (6)	0.3720 (4)	0.2916 (4)	0.017 (2)
H82A	0.4698	0.3441	0.3273	0.020*
C83	0.5402 (6)	0.4276 (5)	0.2918 (3)	0.020 (2)
H83A	0.5745	0.4384	0.3276	0.024*
C84	0.5524 (5)	0.4670 (4)	0.2392 (4)	0.0154 (19)
C85	0.5017 (5)	0.4527 (4)	0.1872 (3)	0.018 (2)
H85A	0.5097	0.4804	0.1515	0.022*
C86	0.4394 (5)	0.3977 (4)	0.1878 (4)	0.019 (2)
H86A	0.4053	0.3871	0.1518	0.022*
C91	−0.0609 (6)	0.2063 (4)	0.2015 (4)	0.015 (2)
C92	−0.0928 (5)	0.1833 (3)	0.2578 (4)	0.0140 (18)
H92A	−0.1378	0.1468	0.2593	0.017*
C93	−0.0607 (6)	0.2121 (4)	0.3123 (3)	0.016 (2)
C94	0.0015 (5)	0.2693 (4)	0.3090 (4)	0.016 (2)
H94A	0.0232	0.2901	0.3458	0.019*
C95	0.0321 (5)	0.2962 (4)	0.2532 (4)	0.0162 (19)
C96	0.0011 (6)	0.2624 (4)	0.2000 (4)	0.017 (2)
H96A	0.0233	0.2785	0.1617	0.021*
C101	−0.0924 (6)	0.1737 (4)	0.1440 (4)	0.015 (2)
C102	−0.0306 (6)	0.1563 (4)	0.0974 (3)	0.0210 (19)
H10A	0.0336	0.1658	0.1027	0.025*
C103	−0.0603 (5)	0.1256 (4)	0.0441 (3)	0.024 (2)
H10B	−0.0172	0.1141	0.0129	0.029*
C104	−0.1542 (6)	0.1116 (4)	0.0365 (3)	0.0185 (19)
C105	−0.2179 (6)	0.1276 (4)	0.0806 (3)	0.023 (2)
H10C	−0.2820	0.1186	0.0743	0.028*
C106	−0.1870 (5)	0.1571 (4)	0.1350 (3)	0.021 (2)
H10D	−0.2302	0.1664	0.1667	0.025*
C111	−0.0870 (5)	0.1820 (4)	0.3723 (4)	0.015 (2)
C112	−0.0983 (5)	0.1094 (4)	0.3795 (3)	0.022 (2)
H11A	−0.0918	0.0793	0.3451	0.027*
C113	−0.1186 (5)	0.0805 (4)	0.4357 (3)	0.0207 (19)
H11B	−0.1248	0.0309	0.4400	0.025*
C114	−0.1298 (5)	0.1244 (4)	0.4859 (3)	0.021 (2)
C115	−0.1206 (5)	0.1962 (4)	0.4807 (4)	0.023 (2)
H11C	−0.1283	0.2257	0.5153	0.028*
C116	−0.0997 (5)	0.2254 (4)	0.4236 (3)	0.019 (2)
H11D	−0.0939	0.2750	0.4195	0.023*
C121	0.0990 (5)	0.3568 (4)	0.2506 (4)	0.0150 (19)
C122	0.1239 (6)	0.3927 (4)	0.3035 (3)	0.021 (2)
H12B	0.0987	0.3779	0.3414	0.025*
C123	0.1856 (5)	0.4506 (4)	0.3025 (3)	0.019 (2)
H12C	0.2034	0.4741	0.3390	0.023*
C124	0.2188 (5)	0.4715 (4)	0.2466 (4)	0.020 (2)
C125	0.1947 (6)	0.4381 (5)	0.1939 (3)	0.026 (2)
H12D	0.2186	0.4540	0.1559	0.031*
C126	0.1352 (6)	0.3808 (4)	0.1959 (3)	0.023 (2)
H12E	0.1189	0.3575	0.1591	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0574 (6)	0.0519 (6)	0.0174 (5)	−0.0165 (5)	−0.0069 (5)	−0.0086 (4)
Br2	0.0582 (6)	0.0457 (6)	0.0178 (5)	−0.0205 (5)	0.0041 (5)	0.0089 (4)
Br3	0.0192 (5)	0.0195 (5)	0.0318 (5)	−0.0041 (4)	0.0000 (4)	−0.0038 (4)
Br4	0.0423 (6)	0.0349 (5)	0.0154 (4)	−0.0078 (4)	−0.0040 (4)	−0.0041 (4)
Br5	0.0398 (6)	0.0539 (6)	0.0171 (5)	−0.0140 (5)	0.0019 (4)	0.0088 (4)
Br6	0.0191 (5)	0.0229 (5)	0.0343 (5)	−0.0054 (4)	−0.0035 (4)	0.0047 (4)
Br7	0.0565 (6)	0.0425 (6)	0.0172 (5)	−0.0209 (5)	−0.0016 (4)	−0.0067 (4)
Br8	0.0344 (5)	0.0357 (6)	0.0146 (4)	−0.0033 (4)	0.0024 (4)	0.0048 (4)
Br9	0.0213 (5)	0.0208 (5)	0.0368 (5)	−0.0041 (4)	0.0042 (4)	−0.0039 (4)
C11	0.013 (5)	0.017 (5)	0.008 (4)	0.005 (4)	0.003 (4)	0.004 (3)
C12	0.017 (5)	0.010 (4)	0.029 (5)	0.003 (3)	0.001 (4)	−0.002 (4)
C13	0.013 (5)	0.017 (5)	0.008 (4)	0.003 (4)	0.001 (4)	0.004 (3)
C14	0.014 (5)	0.023 (5)	0.015 (4)	0.007 (4)	−0.009 (4)	−0.002 (4)
C15	0.015 (5)	0.006 (4)	0.018 (5)	0.007 (4)	0.004 (4)	−0.001 (4)
C16	0.019 (5)	0.010 (5)	0.023 (5)	0.007 (4)	0.001 (4)	0.000 (4)
C21	0.012 (5)	0.014 (4)	0.013 (4)	−0.004 (4)	0.003 (4)	−0.002 (3)
C22	0.022 (5)	0.017 (5)	0.012 (4)	−0.003 (4)	−0.001 (4)	0.004 (3)
C23	0.026 (5)	0.036 (6)	0.015 (5)	−0.008 (4)	0.000 (4)	−0.002 (4)
C24	0.018 (5)	0.039 (6)	0.002 (4)	−0.003 (4)	−0.002 (4)	−0.004 (4)
C25	0.029 (5)	0.017 (5)	0.023 (5)	−0.005 (4)	0.003 (4)	−0.003 (4)
C26	0.024 (5)	0.027 (5)	0.017 (5)	0.001 (4)	0.001 (4)	0.002 (4)
C31	0.019 (5)	0.020 (5)	0.003 (4)	−0.001 (4)	0.003 (4)	−0.001 (4)
C32	0.017 (5)	0.026 (5)	0.018 (5)	0.000 (4)	0.000 (4)	0.003 (4)
C33	0.027 (5)	0.024 (5)	0.027 (5)	−0.008 (4)	0.004 (4)	−0.002 (4)
C34	0.036 (6)	0.023 (5)	0.005 (4)	−0.003 (4)	0.001 (4)	0.006 (4)
C35	0.030 (5)	0.016 (4)	0.022 (5)	−0.006 (4)	0.001 (4)	0.008 (4)
C36	0.015 (5)	0.015 (5)	0.027 (5)	−0.006 (4)	0.000 (4)	0.003 (4)
C41	0.014 (4)	0.016 (4)	0.012 (4)	0.005 (4)	0.000 (4)	0.001 (4)
C42	0.015 (5)	0.027 (5)	0.011 (4)	0.002 (4)	0.004 (4)	0.004 (4)
C43	0.022 (5)	0.016 (5)	0.015 (4)	0.007 (4)	−0.001 (4)	−0.008 (4)
C44	0.011 (4)	0.009 (4)	0.029 (5)	0.001 (3)	0.001 (4)	0.006 (4)
C45	0.029 (5)	0.018 (5)	0.012 (4)	−0.004 (5)	0.004 (4)	−0.003 (4)
C46	0.022 (5)	0.017 (5)	0.012 (4)	0.002 (4)	−0.005 (4)	−0.008 (3)
C51	0.010 (5)	0.010 (5)	0.022 (5)	0.005 (4)	0.002 (4)	0.000 (4)
C52	0.012 (4)	0.015 (4)	0.016 (5)	0.006 (3)	0.000 (4)	−0.002 (4)
C53	0.011 (5)	0.019 (5)	0.016 (5)	0.007 (4)	0.001 (4)	−0.002 (4)
C54	0.013 (5)	0.017 (5)	0.015 (5)	−0.002 (4)	−0.001 (4)	−0.003 (4)
C55	0.014 (5)	0.014 (4)	0.015 (5)	0.000 (4)	0.006 (4)	−0.002 (4)
C56	0.020 (5)	0.020 (5)	0.012 (4)	0.002 (4)	−0.003 (4)	0.001 (4)
C61	0.009 (5)	0.019 (5)	0.018 (5)	0.003 (4)	0.000 (4)	−0.005 (4)
C62	0.032 (5)	0.017 (5)	0.024 (5)	0.000 (4)	−0.002 (4)	0.002 (4)
C63	0.029 (6)	0.023 (5)	0.019 (5)	0.000 (4)	−0.002 (4)	0.002 (3)
C64	0.023 (5)	0.024 (5)	0.010 (4)	−0.006 (4)	0.000 (4)	−0.006 (4)
C65	0.029 (5)	0.019 (4)	0.023 (5)	−0.006 (4)	−0.003 (4)	−0.002 (4)
C66	0.028 (5)	0.017 (5)	0.013 (4)	−0.002 (4)	−0.009 (4)	0.000 (4)
C71	0.008 (5)	0.014 (5)	0.015 (5)	0.003 (4)	−0.004 (4)	0.000 (3)
C72	0.022 (5)	0.023 (5)	0.014 (4)	−0.003 (4)	−0.005 (4)	−0.005 (4)
C73	0.022 (5)	0.018 (5)	0.030 (5)	−0.007 (4)	0.006 (4)	0.003 (4)
C74	0.015 (5)	0.029 (5)	0.017 (5)	−0.010 (4)	0.002 (4)	0.008 (4)
C75	0.032 (5)	0.027 (5)	0.022 (5)	−0.001 (4)	0.004 (5)	−0.006 (4)
C76	0.014 (5)	0.025 (5)	0.022 (5)	0.001 (4)	0.001 (4)	0.003 (4)
C81	0.018 (5)	0.013 (4)	0.011 (4)	−0.006 (4)	0.003 (4)	0.001 (4)
C82	0.009 (5)	0.022 (5)	0.019 (5)	0.001 (4)	0.005 (4)	0.002 (4)
C83	0.015 (5)	0.025 (5)	0.021 (4)	0.004 (5)	−0.001 (4)	−0.005 (4)
C84	0.012 (4)	0.018 (4)	0.016 (4)	−0.006 (4)	−0.002 (4)	0.007 (4)
C85	0.023 (5)	0.020 (5)	0.012 (4)	−0.004 (4)	0.008 (4)	−0.002 (4)
C86	0.018 (5)	0.019 (5)	0.018 (5)	0.005 (4)	−0.002 (4)	−0.006 (4)
C91	0.017 (5)	0.008 (4)	0.019 (5)	0.006 (4)	0.000 (4)	0.001 (3)
C92	0.012 (4)	0.008 (4)	0.022 (5)	0.000 (3)	0.000 (4)	−0.002 (3)
C93	0.022 (5)	0.019 (5)	0.007 (4)	−0.003 (4)	0.006 (4)	−0.005 (4)
C94	0.016 (5)	0.011 (5)	0.021 (5)	0.002 (4)	−0.005 (4)	−0.001 (4)
C95	0.012 (4)	0.020 (5)	0.016 (5)	0.004 (4)	0.000 (5)	0.007 (4)
C96	0.024 (6)	0.015 (5)	0.013 (5)	0.004 (4)	0.000 (4)	−0.001 (4)
C101	0.012 (5)	0.012 (5)	0.020 (5)	0.009 (4)	0.002 (4)	−0.001 (4)
C102	0.022 (5)	0.022 (5)	0.019 (5)	−0.004 (4)	−0.004 (4)	−0.003 (4)
C103	0.032 (5)	0.021 (5)	0.021 (5)	−0.009 (4)	0.007 (4)	0.000 (4)
C104	0.035 (5)	0.011 (4)	0.010 (4)	−0.010 (4)	−0.001 (4)	0.001 (4)
C105	0.020 (5)	0.028 (5)	0.022 (5)	−0.004 (4)	−0.001 (4)	−0.003 (4)
C106	0.027 (5)	0.023 (5)	0.012 (4)	0.008 (4)	0.000 (4)	0.005 (4)
C111	0.010 (5)	0.019 (5)	0.017 (5)	−0.003 (4)	−0.006 (4)	−0.001 (4)
C112	0.030 (5)	0.027 (5)	0.010 (4)	−0.005 (5)	−0.003 (4)	0.001 (4)
C113	0.019 (4)	0.017 (5)	0.026 (5)	−0.001 (4)	0.000 (4)	−0.002 (4)
C114	0.021 (5)	0.026 (5)	0.016 (5)	0.000 (4)	0.008 (4)	0.006 (4)
C115	0.025 (5)	0.033 (5)	0.012 (5)	−0.002 (4)	0.003 (4)	−0.004 (4)
C116	0.014 (5)	0.023 (5)	0.021 (5)	0.001 (4)	0.001 (4)	0.003 (4)
C121	0.012 (4)	0.014 (4)	0.019 (5)	0.009 (4)	0.000 (4)	−0.001 (4)
C122	0.027 (5)	0.022 (5)	0.013 (4)	0.001 (4)	0.003 (4)	0.009 (4)
C123	0.015 (5)	0.027 (5)	0.015 (4)	0.002 (4)	−0.004 (4)	−0.003 (4)
C124	0.012 (4)	0.016 (4)	0.031 (5)	0.000 (4)	0.006 (4)	−0.005 (4)
C125	0.032 (5)	0.028 (5)	0.018 (5)	−0.008 (5)	0.012 (4)	−0.005 (4)
C126	0.030 (5)	0.029 (5)	0.011 (4)	−0.002 (5)	0.001 (4)	−0.003 (4)

Geometric parameters (Å, º) top

Br1—C24	1.903 (7)	C61—C66	1.353 (10)
Br2—C34	1.924 (7)	C61—C62	1.403 (11)
Br3—C44	1.898 (7)	C62—C63	1.391 (10)
Br4—C64	1.894 (7)	C63—C64	1.380 (10)
Br5—C74	1.908 (7)	C64—C65	1.404 (10)
Br6—C84	1.901 (7)	C65—C66	1.402 (9)
Br7—C104	1.906 (7)	C71—C72	1.391 (10)
Br8—C114	1.906 (7)	C71—C76	1.398 (10)
Br9—C124	1.916 (7)	C72—C73	1.374 (10)
C11—C16	1.393 (11)	C73—C74	1.380 (10)
C11—C12	1.393 (11)	C74—C75	1.372 (10)
C11—C21	1.483 (10)	C75—C76	1.411 (10)
C12—C13	1.390 (11)	C81—C82	1.381 (10)
C13—C14	1.395 (11)	C81—C86	1.401 (11)
C13—C31	1.491 (11)	C82—C83	1.392 (11)
C14—C15	1.400 (11)	C83—C84	1.385 (10)
C15—C16	1.397 (11)	C84—C85	1.380 (10)
C15—C41	1.478 (10)	C85—C86	1.376 (11)
C21—C22	1.387 (10)	C91—C92	1.387 (11)
C21—C26	1.392 (10)	C91—C96	1.391 (11)
C22—C23	1.393 (11)	C91—C101	1.475 (11)
C23—C24	1.379 (10)	C92—C93	1.392 (10)
C24—C25	1.365 (10)	C93—C94	1.408 (11)
C25—C26	1.385 (10)	C93—C111	1.483 (11)
C31—C32	1.397 (11)	C94—C95	1.396 (11)
C31—C36	1.399 (10)	C95—C96	1.403 (11)
C32—C33	1.362 (10)	C95—C121	1.501 (10)
C33—C34	1.369 (10)	C101—C102	1.395 (10)
C34—C35	1.376 (10)	C101—C106	1.412 (11)
C35—C36	1.385 (9)	C102—C103	1.372 (9)
C41—C42	1.392 (10)	C103—C104	1.390 (10)
C41—C46	1.394 (10)	C104—C105	1.368 (10)
C42—C43	1.388 (11)	C105—C106	1.390 (10)
C43—C44	1.393 (10)	C111—C112	1.396 (10)
C44—C45	1.386 (10)	C111—C116	1.404 (11)
C45—C46	1.383 (11)	C112—C113	1.379 (10)
C51—C56	1.391 (11)	C113—C114	1.388 (10)
C51—C52	1.399 (11)	C114—C115	1.374 (10)
C51—C61	1.489 (11)	C115—C116	1.401 (10)
C52—C53	1.409 (11)	C121—C126	1.383 (11)
C53—C54	1.393 (11)	C121—C122	1.391 (11)
C53—C71	1.496 (11)	C122—C123	1.413 (11)
C54—C55	1.399 (10)	C123—C124	1.373 (10)
C55—C56	1.389 (11)	C124—C125	1.361 (10)
C55—C81	1.502 (10)	C125—C126	1.385 (12)

C16—C11—C12	118.1 (7)	C61—C66—C65	123.0 (7)
C16—C11—C21	120.4 (7)	C72—C71—C76	118.0 (7)
C12—C11—C21	121.4 (7)	C72—C71—C53	123.2 (7)
C13—C12—C11	121.6 (7)	C76—C71—C53	118.8 (7)
C12—C13—C14	118.6 (7)	C73—C72—C71	122.2 (7)
C12—C13—C31	120.9 (7)	C72—C73—C74	119.0 (7)
C14—C13—C31	120.5 (7)	C75—C74—C73	121.2 (7)
C13—C14—C15	121.7 (7)	C75—C74—Br5	119.0 (6)
C16—C15—C14	117.5 (7)	C73—C74—Br5	119.8 (6)
C16—C15—C41	122.2 (7)	C74—C75—C76	119.5 (7)
C14—C15—C41	120.3 (7)	C71—C76—C75	120.0 (7)
C11—C16—C15	122.3 (7)	C82—C81—C86	118.4 (7)
C22—C21—C26	117.8 (7)	C82—C81—C55	122.0 (7)
C22—C21—C11	122.3 (7)	C86—C81—C55	119.6 (7)
C26—C21—C11	119.9 (7)	C81—C82—C83	120.9 (7)
C21—C22—C23	121.5 (7)	C84—C83—C82	119.3 (7)
C24—C23—C22	118.9 (8)	C85—C84—C83	120.9 (7)
C25—C24—C23	120.7 (7)	C85—C84—Br6	120.1 (6)
C25—C24—Br1	121.1 (6)	C83—C84—Br6	119.1 (6)
C23—C24—Br1	118.2 (6)	C86—C85—C84	119.2 (7)
C24—C25—C26	120.1 (7)	C85—C86—C81	121.3 (7)
C25—C26—C21	120.9 (8)	C92—C91—C96	118.2 (7)
C32—C31—C36	118.3 (7)	C92—C91—C101	121.8 (7)
C32—C31—C13	121.6 (7)	C96—C91—C101	120.0 (7)
C36—C31—C13	120.1 (7)	C91—C92—C93	122.0 (7)
C33—C32—C31	121.6 (8)	C92—C93—C94	118.1 (7)
C32—C33—C34	118.5 (7)	C92—C93—C111	121.6 (7)
C33—C34—C35	123.0 (7)	C94—C93—C111	120.3 (7)
C33—C34—Br2	119.5 (6)	C95—C94—C93	121.8 (8)
C35—C34—Br2	117.6 (6)	C94—C95—C96	117.4 (7)
C34—C35—C36	118.1 (7)	C94—C95—C121	121.1 (7)
C35—C36—C31	120.6 (7)	C96—C95—C121	121.5 (7)
C42—C41—C46	116.9 (7)	C91—C96—C95	122.4 (8)
C42—C41—C15	121.6 (7)	C102—C101—C106	117.6 (7)
C46—C41—C15	121.5 (7)	C102—C101—C91	121.8 (7)
C43—C42—C41	122.7 (7)	C106—C101—C91	120.6 (7)
C42—C43—C44	118.1 (7)	C103—C102—C101	121.6 (8)
C45—C44—C43	121.1 (7)	C102—C103—C104	119.1 (7)
C45—C44—Br3	120.8 (6)	C105—C104—C103	121.8 (7)
C43—C44—Br3	118.1 (6)	C105—C104—Br7	118.8 (6)
C46—C45—C44	118.9 (7)	C103—C104—Br7	119.4 (6)
C45—C46—C41	122.2 (7)	C104—C105—C106	118.7 (7)
C56—C51—C52	118.5 (7)	C105—C106—C101	121.2 (7)
C56—C51—C61	119.5 (7)	C112—C111—C116	118.1 (7)
C52—C51—C61	122.0 (7)	C112—C111—C93	120.7 (7)
C51—C52—C53	121.0 (7)	C116—C111—C93	121.1 (7)
C54—C53—C52	118.9 (7)	C113—C112—C111	121.2 (8)
C54—C53—C71	120.4 (7)	C112—C113—C114	119.6 (7)
C52—C53—C71	120.6 (7)	C115—C114—C113	121.1 (7)
C53—C54—C55	120.7 (7)	C115—C114—Br8	119.6 (6)
C56—C55—C54	119.2 (7)	C113—C114—Br8	119.3 (6)
C56—C55—C81	120.8 (7)	C114—C115—C116	119.1 (8)
C54—C55—C81	119.9 (7)	C115—C116—C111	120.8 (8)
C55—C56—C51	121.7 (7)	C126—C121—C122	117.5 (7)
C66—C61—C62	118.8 (8)	C126—C121—C95	121.9 (7)
C66—C61—C51	122.1 (7)	C122—C121—C95	120.6 (7)
C62—C61—C51	119.1 (7)	C121—C122—C123	122.1 (7)
C63—C62—C61	119.8 (7)	C124—C123—C122	117.1 (7)
C64—C63—C62	120.7 (7)	C125—C124—C123	122.2 (7)
C63—C64—C65	120.1 (7)	C125—C124—Br9	119.4 (6)
C63—C64—Br4	120.8 (6)	C123—C124—Br9	118.3 (6)
C65—C64—Br4	119.1 (6)	C124—C125—C126	119.8 (7)
C66—C65—C64	117.6 (7)	C121—C126—C125	121.3 (7)

C16—C11—C12—C13	−4.3 (11)	C52—C53—C71—C72	27.6 (12)
C21—C11—C12—C13	173.4 (8)	C54—C53—C71—C76	32.0 (11)
C11—C12—C13—C14	0.3 (11)	C52—C53—C71—C76	−152.2 (8)
C11—C12—C13—C31	−178.2 (8)	C76—C71—C72—C73	−4.6 (12)
C12—C13—C14—C15	4.2 (12)	C53—C71—C72—C73	175.6 (7)
C31—C13—C14—C15	−177.3 (8)	C71—C72—C73—C74	3.0 (12)
C13—C14—C15—C16	−4.4 (12)	C72—C73—C74—C75	−0.1 (12)
C13—C14—C15—C41	174.5 (7)	C72—C73—C74—Br5	−179.4 (6)
C12—C11—C16—C15	4.1 (12)	C73—C74—C75—C76	−1.1 (12)
C21—C11—C16—C15	−173.6 (7)	Br5—C74—C75—C76	178.1 (6)
C14—C15—C16—C11	0.1 (12)	C72—C71—C76—C75	3.2 (11)
C41—C15—C16—C11	−178.7 (7)	C53—C71—C76—C75	−177.0 (7)
C16—C11—C21—C22	−34.6 (12)	C74—C75—C76—C71	−0.5 (11)
C12—C11—C21—C22	147.7 (8)	C56—C55—C81—C82	−154.6 (8)
C16—C11—C21—C26	142.8 (8)	C54—C55—C81—C82	23.9 (12)
C12—C11—C21—C26	−34.9 (12)	C56—C55—C81—C86	24.5 (12)
C26—C21—C22—C23	−2.5 (12)	C54—C55—C81—C86	−157.0 (8)
C11—C21—C22—C23	174.9 (7)	C86—C81—C82—C83	1.8 (12)
C21—C22—C23—C24	1.9 (12)	C55—C81—C82—C83	−179.1 (7)
C22—C23—C24—C25	−0.4 (11)	C81—C82—C83—C84	−1.7 (12)
C22—C23—C24—Br1	−178.5 (6)	C82—C83—C84—C85	1.2 (13)
C23—C24—C25—C26	−0.5 (12)	C82—C83—C84—Br6	−178.8 (6)
Br1—C24—C25—C26	177.6 (6)	C83—C84—C85—C86	−1.0 (12)
C24—C25—C26—C21	−0.2 (12)	Br6—C84—C85—C86	179.0 (5)
C22—C21—C26—C25	1.7 (12)	C84—C85—C86—C81	1.2 (12)
C11—C21—C26—C25	−175.8 (7)	C82—C81—C86—C85	−1.6 (12)
C12—C13—C31—C32	−42.3 (12)	C55—C81—C86—C85	179.3 (7)
C14—C13—C31—C32	139.3 (8)	C96—C91—C92—C93	−3.5 (11)
C12—C13—C31—C36	137.3 (8)	C101—C91—C92—C93	177.6 (8)
C14—C13—C31—C36	−41.1 (12)	C91—C92—C93—C94	4.1 (11)
C36—C31—C32—C33	1.3 (12)	C91—C92—C93—C111	−173.0 (8)
C13—C31—C32—C33	−179.1 (7)	C92—C93—C94—C95	−1.1 (12)
C31—C32—C33—C34	−0.7 (12)	C111—C93—C94—C95	176.1 (8)
C32—C33—C34—C35	0.0 (12)	C93—C94—C95—C96	−2.2 (11)
C32—C33—C34—Br2	179.2 (6)	C93—C94—C95—C121	−179.6 (7)
C33—C34—C35—C36	0.2 (12)	C92—C91—C96—C95	0.0 (12)
Br2—C34—C35—C36	−179.0 (5)	C101—C91—C96—C95	178.8 (7)
C34—C35—C36—C31	0.4 (11)	C94—C95—C96—C91	2.8 (11)
C32—C31—C36—C35	−1.1 (11)	C121—C95—C96—C91	−179.9 (7)
C13—C31—C36—C35	179.3 (7)	C92—C91—C101—C102	−135.0 (8)
C16—C15—C41—C42	156.9 (8)	C96—C91—C101—C102	46.2 (11)
C14—C15—C41—C42	−21.9 (11)	C92—C91—C101—C106	43.2 (12)
C16—C15—C41—C46	−22.3 (11)	C96—C91—C101—C106	−135.7 (8)
C14—C15—C41—C46	159.0 (7)	C106—C101—C102—C103	1.5 (11)
C46—C41—C42—C43	1.9 (12)	C91—C101—C102—C103	179.6 (7)
C15—C41—C42—C43	−177.3 (7)	C101—C102—C103—C104	0.0 (12)
C41—C42—C43—C44	0.2 (12)	C102—C103—C104—C105	0.0 (12)
C42—C43—C44—C45	−1.1 (12)	C102—C103—C104—Br7	179.9 (5)
C42—C43—C44—Br3	177.6 (6)	C103—C104—C105—C106	−1.4 (12)
C43—C44—C45—C46	−0.2 (12)	Br7—C104—C105—C106	178.6 (6)
Br3—C44—C45—C46	−178.9 (6)	C104—C105—C106—C101	2.9 (12)
C44—C45—C46—C41	2.5 (12)	C102—C101—C106—C105	−2.9 (12)
C42—C41—C46—C45	−3.3 (11)	C91—C101—C106—C105	178.9 (7)
C15—C41—C46—C45	175.9 (7)	C92—C93—C111—C112	35.5 (12)
C56—C51—C52—C53	1.5 (12)	C94—C93—C111—C112	−141.5 (8)
C61—C51—C52—C53	179.2 (8)	C92—C93—C111—C116	−145.7 (8)
C51—C52—C53—C54	−1.4 (12)	C94—C93—C111—C116	37.2 (12)
C51—C52—C53—C71	−177.4 (7)	C116—C111—C112—C113	−1.8 (12)
C52—C53—C54—C55	1.3 (12)	C93—C111—C112—C113	177.0 (7)
C71—C53—C54—C55	177.3 (7)	C111—C112—C113—C114	1.2 (12)
C53—C54—C55—C56	−1.3 (12)	C112—C113—C114—C115	−0.3 (12)
C53—C54—C55—C81	−179.8 (7)	C112—C113—C114—Br8	−179.6 (6)
C54—C55—C56—C51	1.3 (12)	C113—C114—C115—C116	0.1 (12)
C81—C55—C56—C51	179.8 (7)	Br8—C114—C115—C116	179.4 (6)
C52—C51—C56—C55	−1.4 (12)	C114—C115—C116—C111	−0.8 (12)
C61—C51—C56—C55	−179.2 (8)	C112—C111—C116—C115	1.6 (12)
C56—C51—C61—C66	138.9 (8)	C93—C111—C116—C115	−177.2 (7)
C52—C51—C61—C66	−38.8 (12)	C94—C95—C121—C126	175.3 (8)
C56—C51—C61—C62	−41.1 (12)	C96—C95—C121—C126	−2.0 (12)
C52—C51—C61—C62	141.2 (8)	C94—C95—C121—C122	−7.3 (11)
C66—C61—C62—C63	−1.2 (12)	C96—C95—C121—C122	175.5 (8)
C51—C61—C62—C63	178.9 (7)	C126—C121—C122—C123	−1.5 (11)
C61—C62—C63—C64	0.8 (12)	C95—C121—C122—C123	−179.1 (7)
C62—C63—C64—C65	−0.8 (12)	C121—C122—C123—C124	1.5 (12)
C62—C63—C64—Br4	179.0 (6)	C122—C123—C124—C125	−0.6 (12)
C63—C64—C65—C66	1.1 (12)	C122—C123—C124—Br9	179.7 (5)
Br4—C64—C65—C66	−178.7 (5)	C123—C124—C125—C126	−0.3 (13)
C62—C61—C66—C65	1.5 (13)	Br9—C124—C125—C126	179.4 (6)
C51—C61—C66—C65	−178.5 (7)	C122—C121—C126—C125	0.5 (12)
C64—C65—C66—C61	−1.5 (12)	C95—C121—C126—C125	178.1 (7)
C54—C53—C71—C72	−148.2 (8)	C124—C125—C126—C121	0.4 (13)

Angles (°) between central and terminal phenyl rings in the three independent molecules of (I) top

Molecule 1	Molecule 2	Molecule 3
35.77	40.11	45.92
42.86	30.52	36.35
21.30	24.08	4.74

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1,3,5-Tris(p-bromo­phenyl)­benzene

Supporting information

Key indicators

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1,3,5-Tris(p-bromophenyl)benzene