In the title compound, C22H10Br4, the two outer aromatic rings are offset from the plane occupied by the central ring.
Supporting information
CCDC reference: 283998
Key indicators
- Single-crystal X-ray study
- T = 158 K
- Mean (C-C) = 0.006 Å
- R factor = 0.034
- wR factor = 0.042
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.70 Deg.
| Author Response: Due to the detector configuration employed,
data beyond 0.85 \%A was not collected.
|
Alert level C
THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590
Calculated sin(theta_max)/wavelength = 0.5880
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.70 Deg.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C6 - C7 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C9 ... 1.45 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C13 - C15 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C16 - C17 ... 1.43 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br1 .. 3.49 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact Br4 .. Br4 .. 3.50 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 15
C1 -C6 -C7 -C8 -89.00 12.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 22
C5 -C6 -C7 -C8 87.00 12.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 23
C6 -C7 -C8 -C9 76.00 15.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 24
C7 -C8 -C9 -C10 -138.00 6.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 25
C7 -C8 -C9 -C14 41.00 6.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 36
C12 -C13 -C15 -C16 -148.00 8.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 37
C13 -C15 -C16 -C17 2.00 0.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 38
C14 -C13 -C15 -C16 29.00 8.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 39
C15 -C16 -C17 -C18 1.00 0.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 40
C15 -C16 -C17 -C22 17.00 0.00 1.555 1.555 1.555 1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C22 H10 Br4
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
22 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
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
12 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation and Rigaku, 1998); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN.
1,5-Dibromo-2,4-bis[(2-bromophenyl)ethynyl]benzene
top
Crystal data top
C22H10Br4 | F(000) = 1128 |
Mr = 593.94 | Dx = 2.036 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
a = 10.0580 (7) Å | Cell parameters from 2451 reflections |
b = 8.8663 (6) Å | θ = 2.3–24.6° |
c = 21.870 (2) Å | µ = 8.34 mm−1 |
β = 96.481 (1)° | T = 158 K |
V = 1937.8 (3) Å3 | Tablet, colorless |
Z = 4 | 0.21 × 0.19 × 0.10 mm |
Data collection top
Bruker SMART 1000 diffractometer | 2541 reflections with F2 > 3σ(F2) |
ω scans | Rint = 0.038 |
Absorption correction: empirical (using intensity measurements) (Blessing, 1995) | θmax = 24.7° |
Tmin = 0.189, Tmax = 0.435 | h = 0→11 |
8588 measured reflections | k = 0→10 |
3198 independent reflections | l = −25→25 |
Refinement top
Refinement on F | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo) + 0.00022|Fo|2] |
wR(F2) = 0.042 | (Δ/σ)max < 0.001 |
S = 1.48 | Δρmax = 0.36 e Å−3 |
2541 reflections | Δρmin = −0.64 e Å−3 |
215 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 | −0.01123 (6) | 0.60201 (7) | 0.56742 (3) | 0.0481 (2) | |
Br2 | −0.64754 (5) | 0.39476 (6) | 0.59125 (2) | 0.0347 (2) | |
Br3 | −0.65715 (5) | 0.03578 (6) | 0.37894 (2) | 0.0319 (1) | |
Br4 | −0.01904 (6) | −0.12230 (7) | 0.43676 (3) | 0.0446 (2) | |
C1 | −0.0766 (5) | 0.6509 (5) | 0.6425 (2) | 0.026 (1) | |
C2 | −0.0062 (5) | 0.7525 (5) | 0.6812 (2) | 0.033 (1) | |
C3 | −0.0512 (5) | 0.7875 (6) | 0.7371 (2) | 0.041 (2) | |
C4 | −0.1652 (5) | 0.7200 (5) | 0.7540 (2) | 0.035 (1) | |
C5 | −0.2357 (5) | 0.6202 (5) | 0.7153 (2) | 0.028 (1) | |
C6 | −0.1934 (4) | 0.5828 (5) | 0.6584 (2) | 0.023 (1) | |
C7 | −0.2717 (4) | 0.4835 (5) | 0.6164 (2) | 0.024 (1) | |
C8 | −0.3387 (4) | 0.4061 (5) | 0.5811 (2) | 0.024 (1) | |
C9 | −0.4153 (4) | 0.3151 (5) | 0.5345 (2) | 0.021 (1) | |
C10 | −0.5535 (4) | 0.2994 (5) | 0.5321 (2) | 0.022 (1) | |
C11 | −0.6250 (4) | 0.2159 (5) | 0.4861 (2) | 0.024 (1) | |
C12 | −0.5573 (4) | 0.1463 (5) | 0.4427 (2) | 0.021 (1) | |
C13 | −0.4185 (4) | 0.1554 (5) | 0.4443 (2) | 0.022 (1) | |
C14 | −0.3498 (4) | 0.2406 (5) | 0.4907 (2) | 0.024 (1) | |
C15 | −0.3454 (4) | 0.0754 (5) | 0.4015 (2) | 0.0214 (10) | |
C16 | −0.2798 (4) | 0.0087 (5) | 0.3684 (2) | 0.025 (1) | |
C17 | −0.1999 (4) | −0.0722 (5) | 0.3292 (2) | 0.024 (1) | |
C18 | −0.0809 (5) | −0.1408 (5) | 0.3526 (2) | 0.028 (1) | |
C19 | −0.0048 (5) | −0.2246 (6) | 0.3150 (3) | 0.039 (2) | |
C20 | −0.0479 (5) | −0.2351 (6) | 0.2529 (3) | 0.039 (2) | |
C21 | −0.1645 (5) | −0.1652 (6) | 0.2283 (2) | 0.036 (2) | |
C22 | −0.2398 (5) | −0.0850 (5) | 0.2661 (2) | 0.030 (1) | |
H(1) | 0.0738 | 0.8013 | 0.6676 | 0.0410* | |
H(2) | 0.0023 | 0.8551 | 0.7647 | 0.0462* | |
H(3) | −0.1974 | 0.7481 | 0.7937 | 0.0442* | |
H(4) | −0.3166 | 0.5724 | 0.7264 | 0.0336* | |
H(5) | −0.7221 | 0.2093 | 0.4857 | 0.0302* | |
H(6) | −0.2531 | 0.2469 | 0.4926 | 0.0322* | |
H(7) | 0.0751 | −0.2744 | 0.3322 | 0.0455* | |
H(8) | 0.0066 | −0.2896 | 0.2262 | 0.0477* | |
H(9) | −0.1940 | −0.1777 | 0.1852 | 0.0484* | |
H(10) | −0.3210 | −0.0368 | 0.2473 | 0.0351* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0505 (4) | 0.0535 (4) | 0.0456 (4) | −0.0054 (3) | 0.0281 (3) | −0.0046 (3) |
Br2 | 0.0384 (3) | 0.0347 (3) | 0.0335 (3) | 0.0030 (2) | 0.0154 (2) | −0.0062 (2) |
Br3 | 0.0351 (3) | 0.0316 (3) | 0.0268 (3) | −0.0032 (2) | −0.0063 (2) | −0.0028 (2) |
Br4 | 0.0393 (3) | 0.0597 (4) | 0.0328 (3) | 0.0082 (3) | −0.0042 (2) | 0.0026 (3) |
C1 | 0.027 (3) | 0.022 (3) | 0.028 (3) | 0.002 (2) | 0.003 (2) | 0.002 (2) |
C2 | 0.024 (3) | 0.027 (3) | 0.047 (3) | −0.000 (2) | −0.002 (2) | 0.001 (3) |
C3 | 0.047 (4) | 0.028 (3) | 0.041 (3) | 0.003 (3) | −0.018 (3) | −0.005 (2) |
C4 | 0.050 (3) | 0.029 (3) | 0.025 (3) | 0.003 (3) | 0.002 (2) | −0.005 (2) |
C5 | 0.033 (3) | 0.026 (3) | 0.025 (3) | 0.003 (2) | 0.009 (2) | 0.003 (2) |
C6 | 0.029 (3) | 0.019 (2) | 0.022 (2) | 0.007 (2) | −0.000 (2) | 0.002 (2) |
C7 | 0.02 (8) | 0.0241 | 0.0241 | −0.0000 | 0.0027 | −0.0000 |
C8 | 0.02 (8) | 0.0241 | 0.0241 | −0.0000 | 0.0027 | −0.0000 |
C9 | 0.026 (3) | 0.018 (2) | 0.020 (2) | 0.001 (2) | 0.004 (2) | 0.002 (2) |
C10 | 0.026 (2) | 0.021 (2) | 0.019 (2) | 0.000 (2) | 0.007 (2) | −0.001 (2) |
C11 | 0.022 (2) | 0.023 (3) | 0.027 (3) | 0.004 (2) | 0.002 (2) | 0.006 (2) |
C12 | 0.023 (2) | 0.018 (2) | 0.021 (2) | −0.000 (2) | −0.002 (2) | 0.001 (2) |
C13 | 0.028 (3) | 0.019 (2) | 0.020 (2) | 0.002 (2) | 0.002 (2) | 0.004 (2) |
C14 | 0.022 (2) | 0.026 (3) | 0.022 (2) | 0.000 (2) | −0.000 (2) | 0.004 (2) |
C15 | 0.02 (8) | 0.0214 | 0.0214 | −0.0000 | 0.0024 | −0.0000 |
C16 | 0.03 (8) | 0.0253 | 0.0253 | −0.0000 | 0.0029 | −0.0000 |
C17 | 0.026 (3) | 0.018 (2) | 0.028 (3) | −0.002 (2) | 0.006 (2) | −0.002 (2) |
C18 | 0.028 (3) | 0.027 (3) | 0.030 (3) | −0.005 (2) | 0.004 (2) | −0.001 (2) |
C19 | 0.033 (3) | 0.032 (3) | 0.055 (4) | 0.004 (2) | 0.014 (3) | −0.003 (3) |
C20 | 0.039 (3) | 0.033 (3) | 0.049 (3) | −0.008 (3) | 0.021 (3) | −0.018 (3) |
C21 | 0.041 (3) | 0.038 (3) | 0.031 (3) | −0.010 (3) | 0.010 (2) | −0.014 (2) |
C22 | 0.031 (3) | 0.029 (3) | 0.030 (3) | −0.002 (2) | −0.000 (2) | −0.005 (2) |
Geometric parameters (Å, º) top
Br1—C1 | 1.885 (5) | C13—C15 | 1.437 (6) |
Br2—C10 | 1.887 (4) | C15—C16 | 1.193 (6) |
Br3—C12 | 1.895 (4) | C16—C17 | 1.433 (6) |
Br4—C18 | 1.882 (5) | C17—C18 | 1.387 (6) |
C1—C2 | 1.377 (6) | C17—C22 | 1.398 (6) |
C1—C6 | 1.399 (6) | C18—C19 | 1.398 (7) |
C2—C3 | 1.386 (7) | C19—C20 | 1.384 (8) |
C3—C4 | 1.380 (7) | C20—C21 | 1.381 (7) |
C4—C5 | 1.367 (7) | C21—C22 | 1.380 (7) |
C5—C6 | 1.401 (6) | C2—H(1) | 0.988 |
C6—C7 | 1.438 (6) | C3—H(2) | 0.970 |
C7—C8 | 1.189 (6) | C4—H(3) | 0.991 |
C8—C9 | 1.449 (6) | C5—H(4) | 0.972 |
C9—C10 | 1.391 (6) | C11—H(5) | 0.978 |
C9—C14 | 1.390 (6) | C14—H(6) | 0.970 |
C10—C11 | 1.384 (6) | C19—H(7) | 0.955 |
C11—C12 | 1.376 (6) | C20—H(8) | 0.973 |
C12—C13 | 1.395 (6) | C21—H(9) | 0.962 |
C13—C14 | 1.387 (6) | C22—H(10) | 0.972 |
| | | |
Br1···Br1i | 3.489 (1) | C2···C21iv | 3.561 (7) |
Br3···C4ii | 3.545 (5) | C5···C20v | 3.486 (7) |
Br4···Br4iii | 3.502 (1) | C7···C11vi | 3.561 (6) |
C2···C22iv | 3.423 (7) | C16···C21vii | 3.589 (6) |
C2···C17i | 3.533 (6) | | |
| | | |
Br1—C1—C2 | 118.7 (4) | C16—C17—C22 | 120.9 (4) |
Br1—C1—C6 | 120.2 (3) | C18—C17—C22 | 117.9 (4) |
C2—C1—C6 | 121.1 (4) | Br4—C18—C17 | 119.9 (4) |
C1—C2—C3 | 119.5 (5) | Br4—C18—C19 | 118.5 (4) |
C2—C3—C4 | 120.2 (4) | C17—C18—C19 | 121.5 (4) |
C3—C4—C5 | 120.2 (4) | C18—C19—C20 | 118.8 (5) |
C4—C5—C6 | 121.0 (4) | C19—C20—C21 | 120.7 (5) |
C1—C6—C5 | 117.9 (4) | C20—C21—C22 | 119.8 (5) |
C1—C6—C7 | 121.3 (4) | C17—C22—C21 | 121.2 (4) |
C5—C6—C7 | 120.7 (4) | C1—C2—H(1) | 118.767 |
C6—C7—C8 | 177.7 (5) | C3—C2—H(1) | 121.681 |
C7—C8—C9 | 176.0 (5) | C2—C3—H(2) | 118.354 |
C8—C9—C10 | 122.1 (4) | C4—C3—H(2) | 121.305 |
C8—C9—C14 | 119.5 (4) | C3—C4—H(3) | 119.361 |
C10—C9—C14 | 118.4 (4) | C5—C4—H(3) | 120.350 |
Br2—C10—C9 | 120.3 (3) | C4—C5—H(4) | 121.230 |
Br2—C10—C11 | 118.6 (3) | C6—C5—H(4) | 117.782 |
C9—C10—C11 | 121.1 (4) | C10—C11—H(5) | 118.322 |
C10—C11—C12 | 119.0 (4) | C12—C11—H(5) | 122.649 |
Br3—C12—C11 | 118.5 (3) | C9—C14—H(6) | 119.634 |
Br3—C12—C13 | 119.6 (3) | C13—C14—H(6) | 118.484 |
C11—C12—C13 | 121.9 (4) | C18—C19—H(7) | 120.540 |
C12—C13—C14 | 117.7 (4) | C20—C19—H(7) | 120.679 |
C12—C13—C15 | 122.6 (4) | C19—C20—H(8) | 119.256 |
C14—C13—C15 | 119.7 (4) | C21—C20—H(8) | 119.988 |
C9—C14—C13 | 121.9 (4) | C20—C21—H(9) | 118.998 |
C13—C15—C16 | 176.8 (5) | C22—C21—H(9) | 121.081 |
C15—C16—C17 | 179.3 (5) | C17—C22—H(10) | 121.087 |
C16—C17—C18 | 121.2 (4) | C21—C22—H(10) | 117.753 |
| | | |
Br1—C1—C2—C3 | −178.7 (4) | C7—C8—C9—C14 | 41 (6) |
Br1—C1—C6—C5 | 178.5 (3) | C8—C9—C10—C11 | 177.9 (4) |
Br1—C1—C6—C7 | −4.8 (6) | C8—C9—C14—C13 | −178.3 (4) |
Br2—C10—C9—C8 | −1.2 (6) | C9—C10—C11—C12 | 0.8 (7) |
Br2—C10—C9—C14 | 178.8 (3) | C9—C14—C13—C12 | −0.0 (7) |
Br2—C10—C11—C12 | 179.9 (3) | C9—C14—C13—C15 | −177.5 (4) |
Br3—C12—C11—C10 | −178.7 (3) | C10—C9—C14—C13 | 1.7 (7) |
Br3—C12—C13—C14 | 178.3 (3) | C10—C11—C12—C13 | 1.1 (6) |
Br3—C12—C13—C15 | −4.3 (6) | C11—C10—C9—C14 | −2.1 (6) |
Br4—C18—C17—C16 | −2.2 (6) | C11—C12—C13—C14 | −1.4 (6) |
Br4—C18—C17—C22 | 178.0 (3) | C11—C12—C13—C15 | 176.0 (4) |
Br4—C18—C19—C20 | −178.3 (4) | C12—C13—C15—C16 | −148 (8) |
C1—C2—C3—C4 | 0.4 (7) | C13—C15—C16—C17 | 23 (45) |
C1—C6—C5—C4 | 0.0 (7) | C14—C13—C15—C16 | 29 (8) |
C1—C6—C7—C8 | −89 (12) | C15—C16—C17—C18 | −12 (39) |
C2—C1—C6—C5 | −0.7 (6) | C15—C16—C17—C22 | 167 (38) |
C2—C1—C6—C7 | 176.1 (4) | C16—C17—C18—C19 | 177.7 (4) |
C2—C3—C4—C5 | −1.1 (7) | C16—C17—C22—C21 | −178.8 (5) |
C3—C2—C1—C6 | 0.5 (7) | C17—C18—C19—C20 | 1.8 (8) |
C3—C4—C5—C6 | 0.9 (7) | C17—C22—C21—C20 | 0.5 (8) |
C4—C5—C6—C7 | −176.8 (4) | C18—C17—C22—C21 | 0.9 (7) |
C5—C6—C7—C8 | 87 (12) | C18—C19—C20—C21 | −0.3 (8) |
C6—C7—C8—C9 | 76 (15) | C19—C18—C17—C22 | −2.1 (7) |
C7—C8—C9—C10 | −138 (6) | C19—C20—C21—C22 | −0.8 (8) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, −y, −z+1; (iv) x+1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z+1/2; (vi) −x−1, −y+1, −z+1; (vii) −x−1/2, y+1/2, −z+1/2. |