Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013669/cs2030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013669/cs2030Isup2.hkl |
CCDC reference: 647171
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.087
- Data-to-parameter ratio = 50.0
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.127 0.286 Tmin(prime) and Tmax expected: 0.112 0.189 RR(prime) = 0.748 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.58
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.66 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 40 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.55 su PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.14 Ratio
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.659 Tmax scaled 0.189 Tmin scaled 0.084
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2004); cell refinement: SMART; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C11H8Br2 | Z = 2 |
Mr = 299.99 | F(000) = 288 |
Triclinic, P1 | Dx = 2.063 Mg m−3 |
a = 6.9074 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.3754 (4) Å | Cell parameters from 6376 reflections |
c = 8.5433 (4) Å | θ = 3.0–36.3° |
α = 92.054 (3)° | µ = 8.34 mm−1 |
β = 101.246 (3)° | T = 93 K |
γ = 94.013 (3)° | Splinter, colourless |
V = 482.95 (4) Å3 | 0.25 × 0.21 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 5954 independent reflections |
Radiation source: fine-focus sealed tube | 4333 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
φ and ω scans | θmax = 40.0°, θmin = 4.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −12→12 |
Tmin = 0.127, Tmax = 0.286 | k = −15→15 |
22317 measured reflections | l = −15→15 |
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)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0431P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
5954 reflections | Δρmax = 1.67 e Å−3 |
119 parameters | Δρmin = −2.09 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0081 (15) |
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 | 0.69340 (2) | 0.28597 (2) | 0.70728 (2) | 0.01869 (5) | |
Br2 | 0.12009 (2) | 0.30078 (2) | 0.511045 (19) | 0.01678 (5) | |
C1 | 0.5267 (2) | 0.29026 (19) | 0.85968 (19) | 0.0136 (3) | |
C2 | 0.3543 (2) | 0.36586 (19) | 0.8260 (2) | 0.0153 (3) | |
C3 | 0.2303 (2) | 0.3663 (2) | 0.9413 (2) | 0.0175 (3) | |
H3 | 0.1094 | 0.4163 | 0.9188 | 0.021* | |
C4 | 0.2821 (2) | 0.2964 (2) | 1.0828 (2) | 0.0168 (3) | |
H4 | 0.1976 | 0.2990 | 1.1580 | 0.020* | |
C5 | 0.4612 (2) | 0.21916 (19) | 1.1199 (2) | 0.0145 (3) | |
C6 | 0.5166 (3) | 0.1476 (2) | 1.2673 (2) | 0.0176 (3) | |
H6 | 0.4321 | 0.1497 | 1.3426 | 0.021* | |
C7 | 0.6903 (3) | 0.0753 (2) | 1.3032 (2) | 0.0191 (3) | |
H7 | 0.7257 | 0.0278 | 1.4030 | 0.023* | |
C8 | 0.8167 (3) | 0.0713 (2) | 1.1926 (2) | 0.0192 (3) | |
H8 | 0.9370 | 0.0208 | 1.2180 | 0.023* | |
C9 | 0.7671 (2) | 0.1400 (2) | 1.0477 (2) | 0.0169 (3) | |
H9 | 0.8537 | 0.1365 | 0.9741 | 0.020* | |
C10 | 0.5879 (2) | 0.21609 (19) | 1.00702 (19) | 0.0136 (3) | |
C11 | 0.2902 (3) | 0.4491 (2) | 0.6746 (2) | 0.0189 (3) | |
H11A | 0.4082 | 0.4897 | 0.6341 | 0.023* | |
H11B | 0.2163 | 0.5418 | 0.6963 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01644 (8) | 0.02554 (9) | 0.01503 (8) | 0.00065 (6) | 0.00580 (6) | 0.00088 (6) |
Br2 | 0.01625 (7) | 0.01878 (8) | 0.01400 (8) | 0.00433 (5) | −0.00098 (5) | −0.00090 (6) |
C1 | 0.0131 (6) | 0.0163 (6) | 0.0113 (6) | 0.0001 (5) | 0.0023 (5) | −0.0004 (5) |
C2 | 0.0132 (6) | 0.0163 (6) | 0.0148 (7) | 0.0006 (5) | −0.0003 (5) | 0.0000 (5) |
C3 | 0.0151 (6) | 0.0171 (7) | 0.0185 (7) | 0.0023 (5) | −0.0015 (5) | −0.0011 (6) |
C4 | 0.0134 (6) | 0.0197 (7) | 0.0177 (7) | 0.0013 (5) | 0.0049 (5) | −0.0030 (6) |
C5 | 0.0126 (6) | 0.0143 (6) | 0.0162 (7) | −0.0009 (5) | 0.0031 (5) | −0.0014 (5) |
C6 | 0.0198 (7) | 0.0183 (7) | 0.0139 (7) | −0.0018 (5) | 0.0028 (5) | 0.0003 (6) |
C7 | 0.0223 (7) | 0.0179 (7) | 0.0153 (7) | 0.0007 (6) | −0.0003 (6) | 0.0010 (6) |
C8 | 0.0173 (7) | 0.0176 (7) | 0.0211 (8) | 0.0042 (5) | −0.0013 (6) | −0.0001 (6) |
C9 | 0.0132 (6) | 0.0196 (7) | 0.0173 (7) | 0.0022 (5) | 0.0017 (5) | −0.0018 (6) |
C10 | 0.0123 (6) | 0.0143 (6) | 0.0135 (6) | 0.0010 (5) | 0.0009 (5) | −0.0012 (5) |
C11 | 0.0188 (7) | 0.0164 (7) | 0.0191 (8) | 0.0009 (5) | −0.0021 (6) | 0.0013 (6) |
Br1—C1 | 1.9001 (17) | C5—C6 | 1.410 (2) |
Br1—Br2i | 3.6611 (3) | C5—C10 | 1.424 (2) |
Br2—C11 | 1.9766 (17) | C6—C7 | 1.369 (3) |
Br2—Br1ii | 3.6611 (3) | C6—H6 | 0.9500 |
C1—C2 | 1.374 (2) | C7—C8 | 1.407 (3) |
C1—C10 | 1.426 (2) | C7—H7 | 0.9500 |
C2—C3 | 1.426 (3) | C8—C9 | 1.376 (3) |
C2—C11 | 1.496 (2) | C8—H8 | 0.9500 |
C3—C4 | 1.357 (3) | C9—C10 | 1.420 (2) |
C3—H3 | 0.9500 | C9—H9 | 0.9500 |
C4—C5 | 1.422 (2) | C11—H11A | 0.9900 |
C4—H4 | 0.9500 | C11—H11B | 0.9900 |
C1—Br1—Br2i | 164.36 (5) | C5—C6—H6 | 119.6 |
C11—Br2—Br1ii | 95.20 (6) | C6—C7—C8 | 120.15 (17) |
C2—C1—C10 | 122.36 (15) | C6—C7—H7 | 119.9 |
C2—C1—Br1 | 119.44 (13) | C8—C7—H7 | 119.9 |
C10—C1—Br1 | 118.20 (12) | C9—C8—C7 | 120.42 (16) |
C1—C2—C3 | 118.54 (15) | C9—C8—H8 | 119.8 |
C1—C2—C11 | 123.33 (16) | C7—C8—H8 | 119.8 |
C3—C2—C11 | 118.13 (15) | C8—C9—C10 | 120.79 (16) |
C4—C3—C2 | 121.11 (15) | C8—C9—H9 | 119.6 |
C4—C3—H3 | 119.4 | C10—C9—H9 | 119.6 |
C2—C3—H3 | 119.4 | C9—C10—C5 | 118.24 (15) |
C3—C4—C5 | 120.94 (16) | C9—C10—C1 | 124.05 (16) |
C3—C4—H4 | 119.5 | C5—C10—C1 | 117.71 (14) |
C5—C4—H4 | 119.5 | C2—C11—Br2 | 110.62 (11) |
C6—C5—C4 | 121.13 (16) | C2—C11—H11A | 109.5 |
C6—C5—C10 | 119.53 (15) | Br2—C11—H11A | 109.5 |
C4—C5—C10 | 119.33 (16) | C2—C11—H11B | 109.5 |
C7—C6—C5 | 120.88 (17) | Br2—C11—H11B | 109.5 |
C7—C6—H6 | 119.6 | H11A—C11—H11B | 108.1 |
Br2i—Br1—C1—C2 | 137.78 (14) | C7—C8—C9—C10 | 0.0 (2) |
Br2i—Br1—C1—C10 | −41.3 (3) | C8—C9—C10—C5 | −0.1 (2) |
C10—C1—C2—C3 | −1.6 (2) | C8—C9—C10—C1 | 179.82 (15) |
Br1—C1—C2—C3 | 179.36 (11) | C6—C5—C10—C9 | 0.1 (2) |
C10—C1—C2—C11 | 177.95 (14) | C4—C5—C10—C9 | 179.23 (14) |
Br1—C1—C2—C11 | −1.1 (2) | C6—C5—C10—C1 | −179.81 (14) |
C1—C2—C3—C4 | 1.2 (2) | C4—C5—C10—C1 | −0.7 (2) |
C11—C2—C3—C4 | −178.39 (15) | C2—C1—C10—C9 | −178.51 (15) |
C2—C3—C4—C5 | −0.6 (2) | Br1—C1—C10—C9 | 0.5 (2) |
C3—C4—C5—C6 | 179.42 (16) | C2—C1—C10—C5 | 1.4 (2) |
C3—C4—C5—C10 | 0.3 (2) | Br1—C1—C10—C5 | −179.61 (11) |
C4—C5—C6—C7 | −179.14 (15) | C1—C2—C11—Br2 | 91.78 (17) |
C10—C5—C6—C7 | 0.0 (2) | C3—C2—C11—Br2 | −88.64 (16) |
C5—C6—C7—C8 | −0.1 (3) | Br1ii—Br2—C11—C2 | 71.37 (13) |
C6—C7—C8—C9 | 0.1 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |