Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000571/fl6075sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000571/fl6075Isup2.hkl |
CCDC reference: 234873
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997) and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C6H3Br3O2 | Dx = 2.853 Mg m−3 |
Mr = 346.81 | Melting point: 280 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 12216 reflections |
a = 4.1071 (3) Å | θ = 2.9–27.5° |
b = 12.855 (1) Å | µ = 14.93 mm−1 |
c = 15.296 (1) Å | T = 120 K |
V = 807.6 (1) Å3 | Needle, colourless |
Z = 4 | 0.38 × 0.04 × 0.03 mm |
F(000) = 640 |
Enraf-Nonius KappaCCD diffractometer | 1820 independent reflections |
Radiation source: fine-focus sealed tube | 1390 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.066 |
ω and φ scans | θmax = 27.4°, θmin = 3.1° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −5→5 |
Tmin = 0.067, Tmax = 0.636 | k = −16→16 |
7322 measured reflections | l = −17→19 |
Refinement on F2 | Hydrogen site location: difmap (O-H) and geom (C-H) |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0143P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.056 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.73 e Å−3 |
1820 reflections | Δρmin = −0.63 e Å−3 |
107 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0021 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), 727 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.04 (3) |
Experimental. Melting points were determined on a Gallenkamp melting point apparatus and are uncorrected. IR measurements were recorded on a ATI Mattson Genesis FTIR spectrometer. 250 MHz 1H and 62.5 MHz 13C NMR spectra were determined on a Bruker 250 MHz s pectrometer. TLC chromatography plates were aluminium backed with a coating of Merck 60 F254 silica. |
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 | ||
C1 | 0.7209 (15) | −0.0499 (4) | 0.4241 (4) | 0.0172 (14) | |
C2 | 0.6566 (14) | 0.0039 (4) | 0.3483 (4) | 0.0167 (15) | |
C3 | 0.4764 (15) | 0.0959 (4) | 0.3527 (4) | 0.0172 (15) | |
C4 | 0.3643 (14) | 0.1321 (5) | 0.4326 (4) | 0.0192 (14) | |
H4 | 0.2428 | 0.1949 | 0.4357 | 0.023* | |
C5 | 0.4303 (15) | 0.0766 (4) | 0.5075 (4) | 0.0148 (14) | |
C6 | 0.6087 (15) | −0.0159 (4) | 0.5058 (4) | 0.0176 (14) | |
O1 | 0.7570 (11) | −0.0285 (3) | 0.2683 (3) | 0.0237 (11) | |
H1 | 0.849 (14) | −0.085 (4) | 0.270 (4) | 0.028* | |
O2 | 0.6795 (11) | −0.0752 (3) | 0.5767 (3) | 0.0219 (12) | |
H2 | 0.634 (16) | −0.043 (5) | 0.617 (4) | 0.026* | |
Br1 | 0.95355 (16) | −0.17647 (5) | 0.41737 (4) | 0.02168 (17) | |
Br2 | 0.38328 (13) | 0.17109 (5) | 0.24986 (4) | 0.02274 (18) | |
Br3 | 0.26244 (16) | 0.12500 (5) | 0.61575 (4) | 0.02241 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.022 (3) | 0.012 (3) | 0.018 (4) | 0.004 (3) | −0.003 (3) | −0.003 (3) |
C2 | 0.017 (4) | 0.021 (3) | 0.013 (4) | −0.008 (3) | 0.002 (3) | −0.003 (3) |
C3 | 0.019 (3) | 0.017 (3) | 0.015 (4) | 0.001 (3) | −0.006 (3) | 0.003 (3) |
C4 | 0.021 (4) | 0.015 (3) | 0.022 (4) | −0.001 (3) | −0.006 (3) | 0.001 (3) |
C5 | 0.017 (3) | 0.019 (3) | 0.008 (3) | −0.002 (3) | 0.003 (3) | −0.002 (3) |
C6 | 0.024 (3) | 0.016 (3) | 0.013 (4) | −0.006 (3) | −0.006 (3) | 0.005 (3) |
O1 | 0.033 (2) | 0.020 (2) | 0.018 (3) | 0.004 (2) | 0.005 (2) | −0.003 (2) |
O2 | 0.031 (3) | 0.020 (2) | 0.015 (3) | 0.000 (2) | 0.001 (2) | 0.0017 (19) |
Br1 | 0.0239 (3) | 0.0182 (3) | 0.0230 (4) | 0.0023 (3) | −0.0018 (3) | −0.0014 (3) |
Br2 | 0.0281 (3) | 0.0229 (3) | 0.0173 (4) | 0.0016 (3) | −0.0019 (3) | 0.0025 (3) |
Br3 | 0.0245 (3) | 0.0252 (3) | 0.0175 (3) | 0.0024 (3) | 0.0016 (3) | −0.0007 (3) |
C1—C2 | 1.376 (8) | C4—C5 | 1.377 (8) |
C1—C6 | 1.401 (8) | C4—H4 | 0.9500 |
C1—Br1 | 1.890 (5) | C5—C6 | 1.397 (8) |
C2—O1 | 1.358 (7) | C5—Br3 | 1.898 (6) |
C2—C3 | 1.396 (7) | C6—O2 | 1.358 (7) |
C3—C4 | 1.387 (8) | O1—H1 | 0.82 (5) |
C3—Br2 | 1.886 (6) | O2—H2 | 0.77 (6) |
C2—C1—C6 | 122.1 (5) | C5—C4—H4 | 120.2 |
C2—C1—Br1 | 119.0 (5) | C3—C4—H4 | 120.2 |
C6—C1—Br1 | 118.9 (4) | C4—C5—C6 | 121.9 (5) |
O1—C2—C1 | 123.2 (5) | C4—C5—Br3 | 118.9 (5) |
O1—C2—C3 | 117.7 (5) | C6—C5—Br3 | 119.1 (4) |
C1—C2—C3 | 119.2 (5) | O2—C6—C5 | 125.1 (5) |
C4—C3—C2 | 120.2 (5) | O2—C6—C1 | 117.9 (5) |
C4—C3—Br2 | 119.7 (4) | C5—C6—C1 | 117.1 (5) |
C2—C3—Br2 | 120.1 (5) | C2—O1—H1 | 112 (5) |
C5—C4—C3 | 119.6 (5) | C6—O2—H2 | 107 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Br1 | 0.82 (5) | 2.57 (6) | 3.078 (4) | 121 (5) |
O1—H1···Br3i | 0.82 (5) | 2.90 (6) | 3.298 (4) | 112 (5) |
O2—H2···O1ii | 0.77 (6) | 2.52 (6) | 3.229 (6) | 153 (6) |
O2—H2···Br3 | 0.77 (6) | 2.64 (6) | 3.148 (4) | 125 (6) |
Symmetry codes: (i) −x+3/2, −y, z−1/2; (ii) −x+3/2, −y, z+1/2. |