Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008693/bt6146sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008693/bt6146Isup2.hkl |
CCDC reference: 189413
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.035
- wR factor = 0.044
- Data-to-parameter ratio = 17.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.103
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: EXPOSE in IPDS (Stoe, 1997); cell refinement: CELL in IPDS; data reduction: INTEGRATE in IPDS and X-RED (Stoe, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996).
C12H7Br3O | Dx = 2.092 Mg m−3 |
Mr = 406.91 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 1235 reflections |
a = 15.480 (3) Å | θ = 1.7–26.0° |
b = 5.9692 (9) Å | µ = 9.34 mm−1 |
c = 27.962 (5) Å | T = 293 K |
V = 2583.7 (8) Å3 | Irregular, colourless |
Z = 8 | 0.16 × 0.07 × 0.06 mm |
F(000) = 1536 |
Stoe IPDS area-detector diffractometer | 2513 independent reflections |
Radiation source: fine-focus sealed tube | 1335 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.103 |
Detector resolution: 6.0 pixels mm-1 | θmax = 26.0°, θmin = 2.0° |
area detector scans | h = −19→19 |
Absorption correction: numerical (XRED; Stoe & Cie, 1997) | k = −7→7 |
Tmin = 0.231, Tmax = 0.574 | l = −34→34 |
36351 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.044 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.01P)2] where P = (Fo2 + 2Fc2)/3 |
2513 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.53 e Å−3 |
40 restraints | Δρmin = −0.41 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.64870 (3) | −0.19445 (13) | 0.165844 (15) | 0.0833 (2) | |
Br2 | 0.67846 (2) | 0.17074 (10) | 0.415110 (16) | 0.06006 (14) | |
Br3 | 0.34387 (3) | 0.32515 (11) | 0.486260 (15) | 0.06214 (16) | |
O | 0.59364 (19) | −0.2643 (5) | 0.37919 (10) | 0.0590 (9) | |
C1 | 0.6023 (2) | −0.2375 (8) | 0.33024 (14) | 0.0447 (12) | |
C2 | 0.5668 (3) | −0.0669 (8) | 0.30430 (16) | 0.0560 (13) | |
H2 | 0.5330 | 0.0402 | 0.3196 | 0.067* | |
C3 | 0.5806 (3) | −0.0519 (8) | 0.25538 (16) | 0.0556 (13) | |
H3 | 0.5568 | 0.0657 | 0.2380 | 0.067* | |
C4 | 0.6295 (2) | −0.2111 (9) | 0.23291 (14) | 0.0508 (12) | |
C5 | 0.6660 (3) | −0.3846 (8) | 0.25861 (15) | 0.0587 (13) | |
H5 | 0.6994 | −0.4923 | 0.2433 | 0.070* | |
C6 | 0.6522 (3) | −0.3965 (8) | 0.30768 (15) | 0.0542 (13) | |
H6 | 0.6768 | −0.5122 | 0.3253 | 0.065* | |
C7 | 0.5366 (3) | −0.1259 (8) | 0.40292 (13) | 0.0467 (12) | |
C8 | 0.5628 (2) | 0.0757 (8) | 0.42236 (13) | 0.0408 (11) | |
C9 | 0.5069 (2) | 0.2116 (8) | 0.44708 (12) | 0.0384 (11) | |
H9 | 0.5251 | 0.3483 | 0.4594 | 0.046* | |
C10 | 0.4222 (2) | 0.1388 (8) | 0.45310 (13) | 0.0411 (12) | |
C11 | 0.3956 (3) | −0.0634 (9) | 0.43452 (15) | 0.0537 (13) | |
H11 | 0.3388 | −0.1103 | 0.4387 | 0.064* | |
C12 | 0.4526 (3) | −0.1959 (9) | 0.40987 (15) | 0.0557 (11) | |
H12 | 0.4347 | −0.3334 | 0.3978 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0966 (4) | 0.1040 (6) | 0.0492 (3) | 0.0095 (5) | 0.0052 (3) | −0.0010 (3) |
Br2 | 0.0372 (2) | 0.0669 (3) | 0.0761 (3) | 0.0025 (3) | 0.0028 (2) | 0.0101 (3) |
Br3 | 0.0481 (2) | 0.0738 (4) | 0.0645 (3) | 0.0102 (3) | 0.0116 (2) | 0.0004 (3) |
O | 0.080 (2) | 0.049 (3) | 0.0477 (16) | 0.0253 (17) | 0.0002 (14) | 0.0012 (16) |
C1 | 0.047 (2) | 0.045 (4) | 0.043 (2) | 0.007 (3) | −0.003 (2) | −0.004 (2) |
C2 | 0.059 (3) | 0.052 (4) | 0.057 (3) | 0.022 (3) | −0.004 (2) | −0.002 (3) |
C3 | 0.058 (3) | 0.054 (3) | 0.054 (3) | 0.014 (3) | −0.008 (2) | 0.011 (3) |
C4 | 0.041 (2) | 0.052 (4) | 0.059 (2) | 0.001 (2) | −0.004 (2) | −0.009 (3) |
C5 | 0.052 (3) | 0.057 (4) | 0.068 (3) | 0.016 (3) | 0.004 (2) | −0.009 (2) |
C6 | 0.064 (3) | 0.040 (4) | 0.058 (3) | 0.018 (3) | −0.010 (3) | 0.007 (2) |
C7 | 0.061 (3) | 0.041 (4) | 0.038 (2) | 0.011 (2) | −0.001 (2) | 0.004 (2) |
C8 | 0.039 (2) | 0.044 (3) | 0.040 (3) | 0.011 (2) | −0.0034 (19) | 0.002 (2) |
C9 | 0.040 (2) | 0.032 (3) | 0.043 (2) | 0.003 (2) | −0.0067 (17) | −0.003 (2) |
C10 | 0.038 (2) | 0.048 (4) | 0.038 (2) | −0.001 (2) | −0.0022 (17) | 0.005 (2) |
C11 | 0.043 (3) | 0.059 (4) | 0.059 (3) | −0.011 (3) | 0.000 (2) | 0.003 (3) |
C12 | 0.064 (3) | 0.044 (3) | 0.058 (2) | −0.015 (3) | −0.007 (3) | −0.009 (3) |
Br1—C4 | 1.901 (4) | C7—C8 | 1.381 (5) |
Br2—C8 | 1.889 (4) | C8—C9 | 1.373 (5) |
Br3—C10 | 1.889 (4) | C9—C10 | 1.391 (5) |
O—C7 | 1.380 (5) | C10—C11 | 1.377 (6) |
O—C1 | 1.385 (4) | C11—C12 | 1.371 (6) |
C1—C2 | 1.365 (6) | C2—H2 | 0.9300 |
C1—C6 | 1.377 (6) | C3—H3 | 0.9300 |
C2—C3 | 1.387 (6) | C5—H5 | 0.9300 |
C3—C4 | 1.368 (6) | C6—H6 | 0.9300 |
C4—C5 | 1.381 (6) | C9—H9 | 0.9300 |
C5—C6 | 1.391 (5) | C11—H11 | 0.9300 |
C7—C12 | 1.378 (5) | C12—H12 | 0.9300 |
C7—O—C1 | 117.9 (3) | C11—C10—Br3 | 120.6 (3) |
C2—C1—C6 | 119.8 (4) | C9—C10—Br3 | 118.7 (4) |
C2—C1—O | 124.9 (4) | C12—C11—C10 | 120.2 (4) |
C6—C1—O | 115.3 (4) | C11—C12—C7 | 120.2 (5) |
C1—C2—C3 | 120.6 (4) | C1—C2—H2 | 119.7 |
C4—C3—C2 | 119.6 (4) | C3—C2—H2 | 119.7 |
C3—C4—C5 | 120.6 (4) | C4—C3—H3 | 120.2 |
C3—C4—Br1 | 120.2 (4) | C2—C3—H3 | 120.2 |
C5—C4—Br1 | 119.2 (3) | C4—C5—H5 | 120.4 |
C4—C5—C6 | 119.3 (4) | C6—C5—H5 | 120.4 |
C1—C6—C5 | 120.2 (4) | C1—C6—H6 | 119.9 |
C12—C7—O | 119.3 (4) | C5—C6—H6 | 119.9 |
C12—C7—C8 | 119.0 (4) | C8—C9—H9 | 121.0 |
O—C7—C8 | 121.5 (4) | C10—C9—H9 | 121.0 |
C9—C8—C7 | 121.9 (4) | C12—C11—H11 | 119.9 |
C9—C8—Br2 | 118.3 (3) | C10—C11—H11 | 119.9 |
C7—C8—Br2 | 119.9 (3) | C11—C12—H12 | 119.9 |
C8—C9—C10 | 118.0 (4) | C7—C12—H12 | 119.9 |
C11—C10—C9 | 120.7 (4) | ||
C7—O—C1—C2 | 8.5 (6) | C12—C7—C8—C9 | −2.1 (6) |
C7—O—C1—C6 | −172.7 (4) | O—C7—C8—C9 | −178.3 (3) |
C6—C1—C2—C3 | −0.1 (7) | C12—C7—C8—Br2 | 177.9 (3) |
O—C1—C2—C3 | 178.7 (4) | O—C7—C8—Br2 | 1.8 (5) |
C1—C2—C3—C4 | 0.7 (7) | C7—C8—C9—C10 | 1.3 (6) |
C2—C3—C4—C5 | −0.8 (6) | Br2—C8—C9—C10 | −178.8 (3) |
C2—C3—C4—Br1 | 179.6 (3) | C8—C9—C10—C11 | −0.3 (6) |
C3—C4—C5—C6 | 0.3 (6) | C8—C9—C10—Br3 | −179.1 (3) |
Br1—C4—C5—C6 | 179.8 (3) | C9—C10—C11—C12 | 0.1 (6) |
C2—C1—C6—C5 | −0.5 (7) | Br3—C10—C11—C12 | 179.0 (3) |
O—C1—C6—C5 | −179.3 (4) | C10—C11—C12—C7 | −1.0 (7) |
C4—C5—C6—C1 | 0.4 (6) | O—C7—C12—C11 | 178.2 (4) |
C1—O—C7—C12 | 92.7 (5) | C8—C7—C12—C11 | 2.0 (6) |
C1—O—C7—C8 | −91.2 (5) |