Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021353/ob6105sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021353/ob6105Isup2.hkl |
CCDC reference: 180797
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.024
- wR factor = 0.064
- Data-to-parameter ratio = 16.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.36 From the CIF: _reflns_number_total 2145 Count of symmetry unique reflns 1169 Completeness (_total/calc) 183.49% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 976 Fraction of Friedel pairs measured 0.835 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.
Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001) and ORTEP-32 (Farrugia, 1997).
C10H10Br2O2 | F(000) = 624 |
Mr = 322.00 | Dx = 1.881 Mg m−3 |
Monoclinic, Cc | Melting point: 343(2) K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 5.4507 (2) Å | Cell parameters from 15747 reflections |
b = 18.5945 (9) Å | θ = 0.9–27.1° |
c = 11.4256 (6) Å | µ = 7.10 mm−1 |
β = 100.941 (3)° | T = 295 K |
V = 1136.97 (9) Å3 | Rod, yellow |
Z = 4 | 0.54 × 0.21 × 0.12 mm |
Nonius KappaCCD diffractometer | 2145 independent reflections |
Radiation source: fine-focus sealed tube | 2042 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
φ scans | θmax = 26.4°, θmin = 3.6° |
Absorption correction: empirical (using intensity measurements) (SCALEPACK; Otwinowski & Minor, 1997) | h = −5→5 |
Tmin = 0.180, Tmax = 0.426 | k = −22→22 |
2145 measured reflections | l = −14→14 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.024 | w = 1/[σ2(Fo2) + (0.0396P)2 + 1.0226P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.064 | (Δ/σ)max = 0.004 |
S = 1.04 | Δρmax = 0.53 e Å−3 |
2145 reflections | Δρmin = −0.34 e Å−3 |
131 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0105 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: (Flack, 1983), 976 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.026 (12) |
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 | ||
O1 | 0.6118 (7) | 0.12918 (18) | 0.6483 (3) | 0.0683 (9) | |
C1 | 0.5103 (7) | 0.09766 (19) | 0.7196 (3) | 0.0482 (7) | |
C2 | 0.5612 (7) | 0.0203 (2) | 0.7464 (3) | 0.0488 (8) | |
Br1 | 0.78142 (7) | −0.02215 (2) | 0.65665 (4) | 0.06701 (16) | |
C3 | 0.4630 (8) | −0.01686 (19) | 0.8259 (4) | 0.0489 (9) | |
C7 | 0.5110 (13) | −0.0950 (2) | 0.8549 (5) | 0.0802 (14) | |
H7A | 0.4641 | −0.1232 | 0.7838 | 0.120* | |
H7B | 0.4143 | −0.1098 | 0.9127 | 0.120* | |
H7C | 0.6854 | −0.1020 | 0.8869 | 0.120* | |
C4 | 0.2946 (7) | 0.0223 (2) | 0.8934 (3) | 0.0488 (8) | |
O2 | 0.1980 (7) | −0.0095 (2) | 0.9650 (3) | 0.0719 (9) | |
C5 | 0.2491 (7) | 0.09999 (19) | 0.8687 (3) | 0.0459 (7) | |
Br2 | 0.04670 (6) | 0.14325 (2) | 0.96623 (3) | 0.06778 (17) | |
C6 | 0.3369 (8) | 0.1366 (2) | 0.7847 (3) | 0.0480 (8) | |
C8 | 0.2736 (9) | 0.2142 (2) | 0.7493 (4) | 0.0606 (10) | |
H8 | 0.1531 | 0.2307 | 0.7970 | 0.073* | |
C9 | 0.5040 (11) | 0.2635 (2) | 0.7795 (5) | 0.0750 (13) | |
H9A | 0.6276 | 0.2485 | 0.7348 | 0.113* | |
H9B | 0.5723 | 0.2604 | 0.8632 | 0.113* | |
H9C | 0.4556 | 0.3122 | 0.7592 | 0.113* | |
C10 | 0.1496 (11) | 0.2216 (3) | 0.6200 (5) | 0.0843 (15) | |
H10A | 0.1052 | 0.2710 | 0.6032 | 0.126* | |
H10B | 0.0017 | 0.1925 | 0.6045 | 0.126* | |
H10C | 0.2629 | 0.2062 | 0.5702 | 0.126* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.088 (2) | 0.0629 (17) | 0.0675 (19) | −0.0089 (16) | 0.0494 (17) | −0.0030 (14) |
C1 | 0.049 (2) | 0.0536 (18) | 0.0456 (18) | −0.0051 (15) | 0.0187 (14) | −0.0018 (15) |
C2 | 0.049 (2) | 0.057 (2) | 0.0417 (16) | 0.0015 (15) | 0.0110 (14) | −0.0078 (13) |
Br1 | 0.0641 (3) | 0.0808 (3) | 0.0603 (2) | 0.0180 (2) | 0.02230 (16) | −0.0113 (2) |
C3 | 0.056 (3) | 0.0431 (19) | 0.049 (2) | 0.0021 (14) | 0.0119 (16) | −0.0012 (14) |
C7 | 0.116 (4) | 0.048 (2) | 0.081 (3) | 0.010 (2) | 0.031 (3) | 0.003 (2) |
C4 | 0.048 (2) | 0.056 (2) | 0.0438 (17) | −0.0028 (15) | 0.0138 (14) | 0.0003 (15) |
O2 | 0.076 (2) | 0.0716 (19) | 0.077 (2) | 0.0032 (16) | 0.0386 (18) | 0.0242 (16) |
C5 | 0.046 (2) | 0.0515 (19) | 0.0420 (16) | −0.0006 (14) | 0.0140 (13) | 0.0011 (14) |
Br2 | 0.0760 (3) | 0.0755 (3) | 0.0633 (2) | 0.0104 (2) | 0.04223 (19) | 0.0018 (2) |
C6 | 0.050 (2) | 0.055 (2) | 0.0427 (18) | 0.0050 (14) | 0.0169 (14) | 0.0052 (14) |
C8 | 0.066 (3) | 0.064 (2) | 0.060 (2) | 0.0155 (18) | 0.0317 (18) | 0.0169 (18) |
C9 | 0.090 (3) | 0.051 (2) | 0.081 (3) | 0.008 (2) | 0.008 (2) | −0.004 (2) |
C10 | 0.068 (3) | 0.097 (4) | 0.084 (3) | 0.002 (3) | 0.005 (2) | 0.035 (3) |
O1—C1 | 1.218 (5) | C5—C6 | 1.338 (5) |
C1—C2 | 1.485 (5) | C5—Br2 | 1.890 (4) |
C1—C6 | 1.496 (6) | C6—C8 | 1.519 (6) |
C2—C3 | 1.332 (6) | C8—C10 | 1.510 (6) |
C2—Br1 | 1.893 (4) | C8—C9 | 1.540 (7) |
C3—C4 | 1.494 (6) | C8—H8 | 0.9800 |
C3—C7 | 1.502 (6) | C9—H9A | 0.9600 |
C7—H7A | 0.9600 | C9—H9B | 0.9600 |
C7—H7B | 0.9600 | C9—H9C | 0.9600 |
C7—H7C | 0.9600 | C10—H10A | 0.9600 |
C4—O2 | 1.208 (5) | C10—H10B | 0.9600 |
C4—C5 | 1.485 (5) | C10—H10C | 0.9600 |
O1—C1—C2 | 120.9 (4) | C5—C6—C1 | 117.1 (3) |
O1—C1—C6 | 120.6 (3) | C5—C6—C8 | 125.5 (4) |
C2—C1—C6 | 118.5 (3) | C1—C6—C8 | 117.4 (3) |
C3—C2—C1 | 124.0 (3) | C10—C8—C6 | 112.6 (4) |
C3—C2—Br1 | 122.1 (3) | C10—C8—C9 | 111.0 (4) |
C1—C2—Br1 | 113.9 (3) | C6—C8—C9 | 111.8 (4) |
C2—C3—C4 | 117.7 (3) | C10—C8—H8 | 107.0 |
C2—C3—C7 | 125.2 (4) | C6—C8—H8 | 107.0 |
C4—C3—C7 | 117.1 (4) | C9—C8—H8 | 107.0 |
C3—C7—H7A | 109.5 | C8—C9—H9A | 109.5 |
C3—C7—H7B | 109.5 | C8—C9—H9B | 109.5 |
H7A—C7—H7B | 109.5 | H9A—C9—H9B | 109.5 |
C3—C7—H7C | 109.5 | C8—C9—H9C | 109.5 |
H7A—C7—H7C | 109.5 | H9A—C9—H9C | 109.5 |
H7B—C7—H7C | 109.5 | H9B—C9—H9C | 109.5 |
O2—C4—C5 | 121.7 (4) | C8—C10—H10A | 109.5 |
O2—C4—C3 | 120.1 (4) | C8—C10—H10B | 109.5 |
C5—C4—C3 | 118.2 (3) | H10A—C10—H10B | 109.5 |
C6—C5—C4 | 124.2 (3) | C8—C10—H10C | 109.5 |
C6—C5—Br2 | 122.3 (3) | H10A—C10—H10C | 109.5 |
C4—C5—Br2 | 113.4 (2) | H10B—C10—H10C | 109.5 |
O1—C1—C2—C3 | 177.8 (4) | O2—C4—C5—Br2 | 3.6 (5) |
C6—C1—C2—C3 | −0.5 (5) | C3—C4—C5—Br2 | −176.9 (3) |
O1—C1—C2—Br1 | −2.1 (5) | C4—C5—C6—C1 | −5.7 (6) |
C6—C1—C2—Br1 | 179.5 (3) | Br2—C5—C6—C1 | 175.6 (3) |
C1—C2—C3—C4 | −1.0 (6) | C4—C5—C6—C8 | 173.8 (4) |
Br1—C2—C3—C4 | 179.0 (3) | Br2—C5—C6—C8 | −4.9 (6) |
C1—C2—C3—C7 | −180.0 (5) | O1—C1—C6—C5 | −174.6 (4) |
Br1—C2—C3—C7 | 0.0 (6) | C2—C1—C6—C5 | 3.8 (5) |
C2—C3—C4—O2 | 178.8 (4) | O1—C1—C6—C8 | 5.9 (6) |
C7—C3—C4—O2 | −2.1 (6) | C2—C1—C6—C8 | −175.7 (4) |
C2—C3—C4—C5 | −0.6 (5) | C5—C6—C8—C10 | −119.6 (5) |
C7—C3—C4—C5 | 178.5 (4) | C1—C6—C8—C10 | 59.9 (5) |
O2—C4—C5—C6 | −175.2 (4) | C5—C6—C8—C9 | 114.6 (5) |
C3—C4—C5—C6 | 4.2 (6) | C1—C6—C8—C9 | −65.9 (5) |