The molecule of the title compound, C20H12Br2, has high rigidity and approximate threefold symmetry, but no crystallographically imposed molecular symmetry.
Supporting information
CCDC reference: 245332
Key indicators
- Single-crystal X-ray study
- T = 167 K
- Mean (C-C) = 0.009 Å
- R factor = 0.042
- wR factor = 0.054
- Data-to-parameter ratio = 10.4
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.683 0.855
Tmin and Tmax expected: 0.613 0.855
RR = 1.114
Please check that your absorption correction is appropriate.
GOODF01_ALERT_2_C The least squares goodness of fit parameter lies
outside the range 0.80 <> 2.00
Goodness of fit given = 2.081
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.12
PLAT087_ALERT_2_C Unsatisfactory S value (Too High) .............. 2.08
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.24
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001–2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1998); molecular graphics: TEXSAN; software used to prepare material for publication: TEXSAN.
Crystal data top
C20H12Br2 | F(000) = 808.00 |
Mr = 412.12 | Dx = 1.763 Mg m−3 |
Monoclinic, P21/a | Melting point: 588 K |
Hall symbol: -p 2yab | Mo Kα radiation, λ = 0.7107 Å |
a = 8.0753 (8) Å | Cell parameters from 1610 reflections |
b = 13.698 (1) Å | θ = 2.9–23.1° |
c = 14.054 (1) Å | µ = 5.23 mm−1 |
β = 92.639 (2)° | T = 167 K |
V = 1552.9 (3) Å3 | Parallelepiped, colorless |
Z = 4 | 0.12 × 0.08 × 0.03 mm |
Data collection top
Bruker SMART APEX CCD diffractometer | 2073 reflections with F2 > 3σ(F2) |
ω–scans | Rint = 0.021 |
Absorption correction: multi-scan (Blessing, 1995) | θmax = 26.4° |
Tmin = 0.683, Tmax = 0.855 | h = −10→6 |
9101 measured reflections | k = −17→17 |
3164 independent reflections | l = −17→17 |
Refinement top
Refinement on F | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo) + 0.00022|Fo|2] |
wR(F2) = 0.054 | (Δ/σ)max = 0.006 |
S = 2.08 | Δρmax = 0.74 e Å−3 |
2073 reflections | Δρmin = −0.33 e Å−3 |
199 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 3.0 σ(F2). The
weighted R-factor (wR), goodness of fit (S) and
R-factor (gt) are based on F, with F set to zero for
negative F. The threshold expression of F2 > 3.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.13070 (9) | −0.13790 (5) | 0.93317 (5) | 0.0441 (2) | |
Br2 | 0.20136 (9) | 0.14566 (5) | 0.57093 (5) | 0.0430 (2) | |
C1 | 0.1542 (7) | −0.0522 (4) | 0.8237 (4) | 0.025 (2) | |
C2 | 0.1822 (7) | 0.0606 (4) | 0.6796 (4) | 0.024 (2) | |
C3 | −0.0135 (7) | −0.0185 (4) | 0.7819 (4) | 0.023 (2) | |
C4 | −0.1694 (8) | −0.0410 (4) | 0.8123 (4) | 0.032 (2) | |
C5 | −0.3107 (7) | −0.0049 (5) | 0.7643 (5) | 0.039 (2) | |
C6 | −0.2946 (7) | 0.0546 (5) | 0.6858 (5) | 0.037 (2) | |
C7 | −0.1401 (7) | 0.0783 (4) | 0.6549 (4) | 0.030 (2) | |
C8 | 0.0007 (7) | 0.0425 (4) | 0.7025 (4) | 0.026 (2) | |
C9 | 0.2528 (7) | 0.0397 (4) | 0.8493 (4) | 0.025 (2) | |
C10 | 0.3310 (7) | 0.0627 (5) | 0.9352 (4) | 0.032 (2) | |
C11 | 0.4230 (8) | 0.1484 (5) | 0.9447 (5) | 0.040 (2) | |
C12 | 0.4375 (8) | 0.2095 (4) | 0.8684 (5) | 0.037 (2) | |
C13 | 0.3574 (7) | 0.1863 (4) | 0.7804 (5) | 0.031 (2) | |
C14 | 0.2662 (7) | 0.1010 (4) | 0.7703 (4) | 0.022 (1) | |
C15 | 0.2417 (7) | −0.1025 (4) | 0.7438 (4) | 0.025 (2) | |
C16 | 0.3061 (8) | −0.1957 (4) | 0.7426 (5) | 0.037 (2) | |
C17 | 0.3889 (8) | −0.2267 (5) | 0.6626 (5) | 0.040 (2) | |
C18 | 0.4059 (7) | −0.1659 (5) | 0.5868 (5) | 0.038 (2) | |
C19 | 0.3406 (7) | −0.0717 (4) | 0.5867 (4) | 0.031 (2) | |
C20 | 0.2574 (6) | −0.0408 (4) | 0.6652 (4) | 0.023 (1) | |
H1 | −0.1800 | −0.0815 | 0.8665 | 0.0389* | |
H2 | −0.4175 | −0.0210 | 0.7853 | 0.0465* | |
H3 | −0.3910 | 0.0794 | 0.6529 | 0.0446* | |
H4 | −0.1304 | 0.1191 | 0.6008 | 0.0361* | |
H5 | 0.3224 | 0.0202 | 0.9881 | 0.0388* | |
H6 | 0.4759 | 0.1646 | 1.0044 | 0.0474* | |
H7 | 0.5017 | 0.2674 | 0.8749 | 0.0439* | |
H8 | 0.3658 | 0.2292 | 0.7277 | 0.0374* | |
H9 | 0.2946 | −0.2382 | 0.7952 | 0.0441* | |
H10 | 0.4337 | −0.2908 | 0.6610 | 0.0480* | |
H11 | 0.4632 | −0.1880 | 0.5334 | 0.0456* | |
H12 | 0.3529 | −0.0296 | 0.5338 | 0.0370* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0475 (4) | 0.0473 (4) | 0.0375 (4) | −0.0063 (3) | 0.0024 (3) | 0.0189 (3) |
Br2 | 0.0491 (4) | 0.0440 (4) | 0.0358 (4) | −0.0031 (3) | 0.0026 (3) | 0.0171 (3) |
C1 | 0.026 (3) | 0.025 (3) | 0.026 (3) | −0.001 (3) | 0.000 (3) | 0.006 (2) |
C2 | 0.026 (3) | 0.025 (3) | 0.022 (3) | −0.002 (3) | 0.005 (3) | 0.004 (2) |
C3 | 0.018 (3) | 0.023 (3) | 0.029 (3) | −0.001 (2) | 0.004 (3) | −0.006 (2) |
C4 | 0.027 (4) | 0.037 (3) | 0.034 (4) | −0.008 (3) | 0.010 (3) | −0.007 (3) |
C5 | 0.013 (3) | 0.050 (4) | 0.053 (5) | −0.002 (3) | 0.003 (3) | −0.016 (4) |
C6 | 0.019 (3) | 0.045 (4) | 0.047 (4) | 0.003 (3) | −0.009 (3) | −0.010 (3) |
C7 | 0.026 (3) | 0.031 (3) | 0.033 (4) | −0.002 (3) | −0.003 (3) | −0.008 (3) |
C8 | 0.031 (4) | 0.023 (3) | 0.025 (3) | 0.004 (2) | −0.001 (3) | −0.005 (2) |
C9 | 0.020 (3) | 0.025 (3) | 0.029 (3) | 0.004 (2) | 0.002 (3) | −0.004 (2) |
C10 | 0.032 (4) | 0.039 (4) | 0.026 (3) | 0.012 (3) | 0.003 (3) | −0.002 (3) |
C11 | 0.039 (4) | 0.036 (4) | 0.042 (4) | 0.008 (3) | −0.009 (3) | −0.021 (3) |
C12 | 0.032 (4) | 0.024 (3) | 0.054 (4) | −0.008 (3) | 0.004 (3) | −0.013 (3) |
C13 | 0.020 (3) | 0.027 (3) | 0.047 (4) | 0.001 (3) | 0.007 (3) | −0.000 (3) |
C14 | 0.018 (3) | 0.023 (3) | 0.025 (3) | 0.000 (2) | 0.001 (2) | −0.002 (2) |
C15 | 0.018 (3) | 0.023 (3) | 0.033 (3) | 0.001 (2) | −0.002 (3) | −0.003 (2) |
C16 | 0.035 (4) | 0.025 (3) | 0.049 (4) | 0.000 (3) | −0.005 (3) | 0.001 (3) |
C17 | 0.030 (4) | 0.030 (3) | 0.060 (5) | 0.010 (3) | −0.002 (3) | −0.013 (3) |
C18 | 0.021 (3) | 0.046 (4) | 0.047 (4) | −0.001 (3) | 0.007 (3) | −0.025 (3) |
C19 | 0.024 (3) | 0.038 (3) | 0.030 (3) | −0.008 (3) | 0.000 (3) | −0.009 (3) |
C20 | 0.014 (3) | 0.027 (3) | 0.027 (3) | −0.006 (2) | −0.000 (2) | −0.005 (2) |
Geometric parameters (Å, º) top
Br1—C1 | 1.952 (5) | C13—C14 | 1.385 (8) |
Br2—C2 | 1.933 (5) | C15—C16 | 1.378 (8) |
C1—C3 | 1.523 (8) | C15—C20 | 1.402 (8) |
C1—C9 | 1.524 (8) | C16—C17 | 1.400 (9) |
C1—C15 | 1.519 (8) | C17—C18 | 1.363 (9) |
C2—C8 | 1.535 (8) | C18—C19 | 1.393 (9) |
C2—C14 | 1.521 (7) | C19—C20 | 1.384 (7) |
C2—C20 | 1.532 (7) | C4—H1 | 0.950 |
C3—C4 | 1.382 (8) | C5—H2 | 0.950 |
C3—C8 | 1.403 (8) | C6—H3 | 0.950 |
C4—C5 | 1.389 (8) | C7—H4 | 0.950 |
C5—C6 | 1.383 (9) | C10—H5 | 0.950 |
C6—C7 | 1.379 (8) | C11—H6 | 0.950 |
C7—C8 | 1.382 (8) | C12—H7 | 0.950 |
C9—C10 | 1.373 (8) | C13—H8 | 0.950 |
C9—C14 | 1.401 (7) | C16—H9 | 0.950 |
C10—C11 | 1.392 (9) | C17—H10 | 0.950 |
C11—C12 | 1.370 (9) | C18—H11 | 0.950 |
C12—C13 | 1.405 (9) | C19—H12 | 0.950 |
| | | |
Br1···C11i | 3.431 (6) | Br2···C18ii | 3.486 (6) |
Br1···C12i | 3.549 (6) | | |
| | | |
Br1—C1—C3 | 111.7 (4) | C1—C15—C20 | 111.8 (5) |
Br1—C1—C9 | 112.3 (4) | C16—C15—C20 | 120.1 (5) |
Br1—C1—C15 | 112.1 (4) | C15—C16—C17 | 119.0 (6) |
C3—C1—C9 | 106.6 (4) | C16—C17—C18 | 120.7 (6) |
C3—C1—C15 | 106.8 (5) | C17—C18—C19 | 121.0 (6) |
C9—C1—C15 | 107.1 (4) | C18—C19—C20 | 118.7 (6) |
Br2—C2—C8 | 112.0 (4) | C2—C20—C15 | 113.0 (5) |
Br2—C2—C14 | 113.2 (4) | C2—C20—C19 | 126.3 (5) |
Br2—C2—C20 | 113.3 (4) | C15—C20—C19 | 120.5 (5) |
C8—C2—C14 | 106.0 (4) | C3—C4—H1 | 119.7 |
C8—C2—C20 | 105.7 (4) | C5—C4—H1 | 119.6 |
C14—C2—C20 | 106.1 (4) | C4—C5—H2 | 120.3 |
C1—C3—C4 | 128.3 (5) | C6—C5—H2 | 120.3 |
C1—C3—C8 | 112.5 (5) | C5—C6—H3 | 119.7 |
C4—C3—C8 | 119.2 (5) | C7—C6—H3 | 119.7 |
C3—C4—C5 | 120.7 (6) | C6—C7—H4 | 120.0 |
C4—C5—C6 | 119.4 (5) | C8—C7—H4 | 120.0 |
C5—C6—C7 | 120.7 (6) | C9—C10—H5 | 120.0 |
C6—C7—C8 | 120.0 (6) | C11—C10—H5 | 120.0 |
C2—C8—C3 | 112.1 (5) | C10—C11—H6 | 119.9 |
C2—C8—C7 | 127.8 (5) | C12—C11—H6 | 119.9 |
C3—C8—C7 | 120.0 (5) | C11—C12—H7 | 120.0 |
C1—C9—C10 | 127.8 (5) | C13—C12—H7 | 120.0 |
C1—C9—C14 | 111.5 (5) | C12—C13—H8 | 119.9 |
C10—C9—C14 | 120.6 (5) | C14—C13—H8 | 119.9 |
C9—C10—C11 | 120.0 (6) | C15—C16—H9 | 120.5 |
C10—C11—C12 | 120.3 (6) | C17—C16—H9 | 120.5 |
C11—C12—C13 | 119.9 (5) | C16—C17—H10 | 119.7 |
C12—C13—C14 | 120.1 (6) | C18—C17—H10 | 119.7 |
C2—C14—C9 | 113.5 (5) | C17—C18—H11 | 119.5 |
C2—C14—C13 | 127.4 (5) | C19—C18—H11 | 119.5 |
C9—C14—C13 | 119.0 (5) | C18—C19—H12 | 120.6 |
C1—C15—C16 | 128.1 (5) | C20—C19—H12 | 120.7 |
| | | |
Br1—C1—C3—C4 | 0.3 (7) | C4—C3—C1—C9 | −122.7 (6) |
Br1—C1—C3—C8 | −179.5 (4) | C4—C3—C1—C15 | 123.1 (6) |
Br1—C1—C9—C10 | 4.7 (7) | C4—C3—C8—C7 | −1.0 (8) |
Br1—C1—C9—C14 | −179.1 (4) | C4—C5—C6—C7 | 0.0 (9) |
Br1—C1—C15—C16 | −2.0 (8) | C5—C4—C3—C8 | 0.9 (8) |
Br1—C1—C15—C20 | 179.7 (4) | C5—C6—C7—C8 | −0.1 (9) |
Br2—C2—C8—C3 | −179.5 (4) | C7—C8—C2—C14 | 124.8 (6) |
Br2—C2—C8—C7 | 0.9 (7) | C7—C8—C2—C20 | −122.9 (6) |
Br2—C2—C14—C9 | −180.0 (4) | C8—C2—C14—C9 | 56.9 (6) |
Br2—C2—C14—C13 | −3.5 (7) | C8—C2—C14—C13 | −126.6 (6) |
Br2—C2—C20—C15 | −179.4 (4) | C8—C2—C20—C15 | −56.4 (6) |
Br2—C2—C20—C19 | 3.5 (7) | C8—C2—C20—C19 | 126.5 (6) |
C1—C3—C4—C5 | −178.8 (5) | C8—C3—C1—C9 | 57.5 (6) |
C1—C3—C8—C2 | −0.9 (6) | C8—C3—C1—C15 | −56.7 (6) |
C1—C3—C8—C7 | 178.8 (5) | C9—C1—C15—C16 | 121.5 (6) |
C1—C9—C10—C11 | 176.8 (5) | C9—C1—C15—C20 | −56.8 (6) |
C1—C9—C14—C2 | −0.8 (6) | C9—C10—C11—C12 | −0.8 (9) |
C1—C9—C14—C13 | −177.6 (5) | C9—C14—C2—C20 | −55.2 (6) |
C1—C15—C16—C17 | −177.3 (6) | C9—C14—C13—C12 | 1.2 (8) |
C1—C15—C20—C2 | −0.3 (7) | C10—C9—C1—C15 | −118.7 (6) |
C1—C15—C20—C19 | 177.0 (5) | C10—C9—C14—C13 | −1.1 (8) |
C2—C8—C3—C4 | 179.3 (5) | C10—C11—C12—C13 | 0.9 (9) |
C2—C8—C7—C6 | −179.8 (5) | C11—C10—C9—C14 | 0.9 (8) |
C2—C14—C9—C10 | 175.8 (5) | C11—C12—C13—C14 | −1.1 (9) |
C2—C14—C13—C12 | −175.2 (5) | C(13—C14—C2—C20 | 121.4 (6) |
C2—C20—C15—C16 | −178.7 (5) | C14—C2—C20—C15 | 55.8 (6) |
C2—C20—C19—C18 | 177.9 (5) | C14—C2—C20—C19 | −121.2 (6) |
C3—C1—C9—C10 | 127.3 (6) | C14—C9—C1—C15 | 57.6 (6) |
C3—C1—C9—C14 | −56.5 (6) | C15—C16—C17—C18 | 0.0 (10) |
C3—C1—C15—C16 | −124.6 (6) | C15—C20—C19—C18 | 1.0 (8) |
C3—C1—C15—C20 | 57.1 (6) | C16—C15—C20—C19 | −1.5 (9) |
C3—C4—C5—C6 | −0.5 (9) | C16—C17—C18—C19 | 0 (1) |
C3—C8—C2—C14 | −55.6 (6) | C17—C16—C15—C20 | 0.9 (9) |
C3—C8—C2—C20 | 56.8 (6) | C17—C18—C19—C20 | −0.1 (9) |
C3—C8—C7—C6 | 0.6 (8) | | |
Symmetry codes: (i) −x+1/2, y−1/2, −z+2; (ii) −x+1/2, y+1/2, −z+1. |