Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037949/ya2026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037949/ya2026Isup2.hkl |
CCDC reference: 625055
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.018 Å
- R factor = 0.070
- wR factor = 0.150
- Data-to-parameter ratio = 19.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 18
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.142 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.14 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.23 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C12 H12 Br4 O2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C12H12Br4O2 | F(000) = 960 |
Mr = 507.82 | Dx = 2.256 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4073 reflections |
a = 17.546 (5) Å | θ = 2.1–24.3° |
b = 12.522 (5) Å | µ = 10.76 mm−1 |
c = 7.405 (5) Å | T = 296 K |
β = 113.207 (5)° | Prism, colourless |
V = 1495.3 (12) Å3 | 0.28 × 0.23 × 0.16 mm |
Z = 4 |
Stoe IPDS II diffractometer | 1611 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 797 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.142 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.1°, θmin = 2.1° |
ω scans | h = −22→22 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −16→15 |
Tmin = 0.084, Tmax = 0.203 | l = −9→9 |
6748 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)] = 0.070 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0498P)2 + 0.9739P] where P = (Fo2 + 2Fc2)/3 |
1611 reflections | (Δ/σ)max = 0.001 |
82 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.77 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.19717 (12) | 1.04368 (15) | 0.3341 (2) | 0.1433 (8) | |
Br2 | 0.07083 (7) | 1.36218 (9) | 0.58829 (16) | 0.0740 (4) | |
O1 | 0.1061 (4) | 1.2535 (6) | 0.1056 (9) | 0.072 (3) | |
C1 | 0.0435 (10) | 0.9536 (10) | 0.268 (2) | 0.127 (8) | |
C2 | 0.0824 (9) | 1.0510 (10) | 0.2830 (14) | 0.095 (5) | |
C3 | 0.0427 (6) | 1.1449 (7) | 0.2669 (12) | 0.061 (3) | |
C4 | 0.0898 (6) | 1.2484 (7) | 0.2789 (13) | 0.054 (3) | |
C5 | 0.0468 (6) | 1.3467 (7) | 0.3054 (13) | 0.057 (3) | |
C6 | 0.1765 (7) | 1.3157 (13) | 0.128 (2) | 0.113 (6) | |
H1 | 0.07250 | 0.88990 | 0.28020 | 0.1530* | |
H4 | 0.14310 | 1.24310 | 0.39150 | 0.0650* | |
H5 | 0.06960 | 1.40860 | 0.26290 | 0.0680* | |
H6A | 0.18360 | 1.31740 | 0.00600 | 0.1700* | |
H6B | 0.22480 | 1.28470 | 0.22810 | 0.1700* | |
H6C | 0.16900 | 1.38700 | 0.16540 | 0.1700* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1554 (15) | 0.1830 (17) | 0.0819 (9) | 0.1213 (14) | 0.0366 (9) | 0.0053 (9) |
Br2 | 0.0845 (8) | 0.0729 (7) | 0.0622 (6) | 0.0003 (6) | 0.0265 (5) | −0.0178 (6) |
O1 | 0.073 (5) | 0.093 (5) | 0.057 (4) | −0.004 (4) | 0.033 (4) | −0.018 (4) |
C1 | 0.25 (2) | 0.068 (8) | 0.059 (7) | 0.068 (10) | 0.057 (15) | 0.019 (7) |
C2 | 0.159 (13) | 0.069 (8) | 0.045 (6) | 0.047 (8) | 0.026 (7) | 0.009 (5) |
C3 | 0.084 (6) | 0.056 (5) | 0.043 (5) | 0.015 (5) | 0.024 (5) | 0.004 (5) |
C4 | 0.047 (5) | 0.047 (5) | 0.057 (5) | 0.003 (4) | 0.009 (4) | −0.006 (4) |
C5 | 0.072 (6) | 0.041 (5) | 0.060 (5) | 0.004 (4) | 0.028 (5) | 0.000 (4) |
C6 | 0.065 (7) | 0.186 (14) | 0.111 (10) | −0.042 (9) | 0.059 (7) | −0.032 (10) |
Br1—C2 | 1.899 (16) | C4—C5 | 1.497 (14) |
Br2—C5 | 1.977 (9) | C5—C5i | 1.519 (15) |
O1—C4 | 1.422 (12) | C1—H1 | 0.9312 |
O1—C6 | 1.414 (16) | C4—H4 | 0.9796 |
C1—C2 | 1.381 (19) | C5—H5 | 0.9793 |
C1—C1i | 1.44 (3) | C6—H6A | 0.9596 |
C2—C3 | 1.348 (16) | C6—H6B | 0.9609 |
C3—C4 | 1.521 (13) | C6—H6C | 0.9591 |
C3—C3i | 1.419 (16) | ||
Br1···O1 | 3.192 (8) | C6···Br2vii | 3.730 (14) |
Br1···C6 | 3.692 (16) | C6···Br1viii | 3.557 (16) |
Br1···Br1ii | 3.861 (3) | C5···H6C | 2.7710 |
Br1···C6iii | 3.557 (16) | C6···H5 | 2.7103 |
Br1···Br1iv | 3.861 (3) | H1···O1ii | 2.8738 |
Br2···C6v | 3.730 (14) | H4···Br1 | 2.7630 |
Br2···O1i | 3.168 (8) | H4···H6B | 2.2710 |
Br1···H6Ciii | 3.0588 | H5···C6 | 2.7103 |
Br1···H4 | 2.7630 | H5···H6C | 2.1514 |
Br1···H6B | 3.2031 | H5···Br2ix | 3.1516 |
Br2···H6Av | 2.9956 | H6A···Br2vii | 2.9956 |
Br2···H5vi | 3.1516 | H6B···Br1 | 3.2031 |
O1···Br1 | 3.192 (8) | H6B···H4 | 2.2710 |
O1···Br2i | 3.168 (8) | H6C···C5 | 2.7710 |
O1···H1iv | 2.8738 | H6C···H5 | 2.1514 |
C6···Br1 | 3.692 (16) | H6C···Br1viii | 3.0588 |
C4—O1—C6 | 113.3 (8) | C2—C1—H1 | 121.00 |
C1i—C1—C2 | 117.9 (13) | C1i—C1—H1 | 121.06 |
Br1—C2—C1 | 115.2 (11) | O1—C4—H4 | 107.89 |
Br1—C2—C3 | 122.0 (10) | C3—C4—H4 | 107.85 |
C1—C2—C3 | 122.8 (15) | C5—C4—H4 | 107.80 |
C2—C3—C4 | 119.2 (11) | Br2—C5—H5 | 108.63 |
C2—C3—C3i | 119.3 (10) | C4—C5—H5 | 108.54 |
C3i—C3—C4 | 121.5 (8) | C5i—C5—H5 | 108.54 |
O1—C4—C3 | 106.5 (7) | O1—C6—H6A | 109.47 |
O1—C4—C5 | 111.9 (7) | O1—C6—H6B | 109.40 |
C3—C4—C5 | 114.7 (9) | O1—C6—H6C | 109.50 |
Br2—C5—C4 | 108.2 (6) | H6A—C6—H6B | 109.45 |
Br2—C5—C5i | 107.8 (7) | H6A—C6—H6C | 109.55 |
C4—C5—C5i | 115.0 (8) | H6B—C6—H6C | 109.45 |
C6—O1—C4—C3 | −154.3 (9) | C3i—C3—C4—C5 | 15.3 (12) |
C6—O1—C4—C5 | 79.6 (11) | C2—C3—C3i—C4i | 177.8 (8) |
C1i—C1—C2—C3 | 0.5 (18) | C4—C3—C3i—C2i | 177.8 (8) |
C1i—C1—C2—Br1 | 179.2 (10) | C4—C3—C3i—C4i | −4.2 (12) |
C2—C1—C1i—C2i | −0.7 (19) | O1—C4—C5—C5i | 84.2 (10) |
Br1—C2—C3—C3i | −178.6 (6) | C3—C4—C5—Br2 | 83.3 (8) |
Br1—C2—C3—C4 | 3.4 (12) | C3—C4—C5—C5i | −37.3 (11) |
C1—C2—C3—C4 | −178.1 (10) | O1—C4—C5—Br2 | −155.3 (7) |
C1—C2—C3—C3i | 0.0 (15) | C4—C5—C5i—C4i | 49.7 (11) |
C2—C3—C3i—C2i | −0.3 (13) | Br2—C5—C5i—C4i | −71.1 (8) |
C2—C3—C4—O1 | 69.0 (10) | C4—C5—C5i—Br2i | −71.1 (8) |
C2—C3—C4—C5 | −166.7 (8) | Br2—C5—C5i—Br2i | 168.2 (4) |
C3i—C3—C4—O1 | −109.0 (9) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y+2, z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x, −y+2, z−1/2; (v) x, y, z+1; (vi) x, −y+3, z+1/2; (vii) x, y, z−1; (viii) −x+1/2, y+1/2, −z+1/2; (ix) x, −y+3, z−1/2. |