Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026262/bv2023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026262/bv2023Isup2.hkl |
CCDC reference: 620704
Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure.
C10H10Br2O2 | Dx = 1.800 Mg m−3 |
Mr = 321.98 | Melting point: 345 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 4.129 (2) Å | Cell parameters from 1498 reflections |
b = 11.192 (6) Å | θ = 2.4–22.5° |
c = 25.732 (15) Å | µ = 6.80 mm−1 |
β = 92.274 (10)° | T = 294 K |
V = 1188.2 (11) Å3 | Block, colorless |
Z = 4 | 0.26 × 0.24 × 0.12 mm |
F(000) = 624 |
CCD area detector diffractometer | 2086 independent reflections |
Radiation source: fine-focus sealed tube | 1422 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
phi and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −4→4 |
Tmin = 0.186, Tmax = 0.442 | k = −13→12 |
5582 measured reflections | l = −30→23 |
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)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.194 | w = 1/[σ2(Fo2) + (0.0831P)2 + 5.9795P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max < 0.001 |
2086 reflections | Δρmax = 1.00 e Å−3 |
130 parameters | Δρmin = −0.82 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.013 (2) |
Experimental. Spectroscopic analysis: 1H NMR (CDCl3, δ, p.p.m.): 7.41 (s, 1H), 6.68 (d, J = 2.1 Hz, 2H), 6.44 (brs, 1H), 3.79(s, 6H). |
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 | 0.6528 (3) | 0.66784 (10) | 0.20443 (5) | 0.0506 (5) | |
Br2 | 0.3449 (3) | 0.40741 (10) | 0.22553 (4) | 0.0452 (5) | |
O1 | 0.051 (2) | 0.3094 (7) | −0.0342 (3) | 0.051 (2) | |
O2 | 0.497 (2) | 0.0420 (6) | 0.1005 (3) | 0.050 (2) | |
C1 | 0.512 (2) | 0.5157 (9) | 0.1750 (4) | 0.033 (2) | |
C2 | 0.543 (3) | 0.4929 (10) | 0.1230 (4) | 0.039 (3) | |
H2 | 0.6288 | 0.5540 | 0.1033 | 0.047* | |
C3 | 0.451 (3) | 0.3786 (9) | 0.0943 (4) | 0.031 (2) | |
C4 | 0.301 (3) | 0.3912 (9) | 0.0442 (4) | 0.038 (3) | |
H4 | 0.2620 | 0.4670 | 0.0304 | 0.046* | |
C5 | 0.208 (3) | 0.2878 (9) | 0.0148 (4) | 0.033 (2) | |
C6 | 0.273 (3) | 0.1721 (10) | 0.0350 (4) | 0.039 (3) | |
H6 | 0.2106 | 0.1046 | 0.0160 | 0.046* | |
C7 | 0.434 (3) | 0.1605 (9) | 0.0842 (4) | 0.040 (3) | |
C8 | 0.527 (3) | 0.2618 (10) | 0.1142 (4) | 0.036 (3) | |
H8 | 0.6367 | 0.2528 | 0.1463 | 0.043* | |
C9 | −0.067 (3) | 0.2056 (11) | −0.0643 (5) | 0.052 (3) | |
H9A | 0.1122 | 0.1548 | −0.0720 | 0.078* | |
H9B | −0.1718 | 0.2323 | −0.0962 | 0.078* | |
H9C | −0.2190 | 0.1618 | −0.0444 | 0.078* | |
C10 | 0.663 (3) | 0.0253 (11) | 0.1518 (4) | 0.055 (3) | |
H10A | 0.8838 | 0.0518 | 0.1503 | 0.082* | |
H10B | 0.6598 | −0.0578 | 0.1611 | 0.082* | |
H10C | 0.5543 | 0.0709 | 0.1775 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0625 (9) | 0.0327 (7) | 0.0561 (9) | −0.0036 (6) | −0.0049 (6) | −0.0132 (5) |
Br2 | 0.0551 (8) | 0.0426 (7) | 0.0387 (7) | −0.0003 (6) | 0.0122 (5) | 0.0025 (5) |
O1 | 0.079 (6) | 0.038 (4) | 0.033 (4) | −0.001 (4) | −0.008 (4) | −0.004 (3) |
O2 | 0.073 (6) | 0.027 (4) | 0.049 (5) | 0.010 (4) | −0.013 (4) | 0.000 (4) |
C1 | 0.035 (6) | 0.032 (6) | 0.032 (6) | 0.000 (5) | −0.009 (5) | 0.000 (4) |
C2 | 0.045 (7) | 0.033 (6) | 0.038 (6) | −0.008 (5) | −0.009 (5) | 0.005 (5) |
C3 | 0.039 (6) | 0.031 (5) | 0.025 (5) | −0.006 (5) | 0.009 (4) | −0.006 (4) |
C4 | 0.050 (7) | 0.026 (6) | 0.039 (6) | 0.002 (5) | 0.006 (5) | 0.001 (5) |
C5 | 0.040 (6) | 0.031 (6) | 0.029 (6) | −0.001 (5) | 0.005 (5) | 0.004 (4) |
C6 | 0.051 (7) | 0.038 (6) | 0.027 (6) | 0.004 (5) | 0.011 (5) | 0.000 (5) |
C7 | 0.055 (7) | 0.026 (5) | 0.038 (6) | −0.001 (5) | 0.011 (5) | 0.002 (5) |
C8 | 0.039 (6) | 0.040 (6) | 0.029 (6) | 0.003 (5) | 0.009 (5) | 0.007 (5) |
C9 | 0.066 (9) | 0.054 (8) | 0.034 (6) | −0.010 (7) | −0.015 (6) | −0.011 (6) |
C10 | 0.075 (9) | 0.049 (7) | 0.039 (7) | 0.018 (7) | −0.007 (6) | 0.003 (6) |
Br1—C1 | 1.944 (10) | C4—H4 | 0.9300 |
Br2—C1 | 1.925 (11) | C5—C6 | 1.417 (15) |
O1—C5 | 1.415 (13) | C6—C7 | 1.413 (15) |
O1—C9 | 1.469 (13) | C6—H6 | 0.9300 |
O2—C7 | 1.412 (13) | C7—C8 | 1.416 (15) |
O2—C10 | 1.475 (13) | C8—H8 | 0.9300 |
C1—C2 | 1.371 (14) | C9—H9A | 0.9600 |
C2—C3 | 1.517 (14) | C9—H9B | 0.9600 |
C2—H2 | 0.9300 | C9—H9C | 0.9600 |
C3—C4 | 1.418 (15) | C10—H10A | 0.9600 |
C3—C8 | 1.434 (14) | C10—H10B | 0.9600 |
C4—C5 | 1.425 (15) | C10—H10C | 0.9600 |
C5—O1—C9 | 117.8 (8) | C5—C6—H6 | 120.4 |
C7—O2—C10 | 117.3 (9) | O2—C7—C6 | 115.3 (9) |
C2—C1—Br2 | 126.3 (8) | O2—C7—C8 | 123.2 (10) |
C2—C1—Br1 | 120.3 (8) | C6—C7—C8 | 121.5 (10) |
Br2—C1—Br1 | 113.4 (5) | C7—C8—C3 | 119.0 (10) |
C1—C2—C3 | 126.9 (10) | C7—C8—H8 | 120.5 |
C1—C2—H2 | 116.6 | C3—C8—H8 | 120.5 |
C3—C2—H2 | 116.6 | O1—C9—H9A | 109.5 |
C4—C3—C8 | 119.8 (9) | O1—C9—H9B | 109.5 |
C4—C3—C2 | 116.8 (9) | H9A—C9—H9B | 109.5 |
C8—C3—C2 | 123.2 (9) | O1—C9—H9C | 109.5 |
C3—C4—C5 | 120.0 (9) | H9A—C9—H9C | 109.5 |
C3—C4—H4 | 120.0 | H9B—C9—H9C | 109.5 |
C5—C4—H4 | 120.0 | O2—C10—H10A | 109.5 |
O1—C5—C6 | 123.7 (9) | O2—C10—H10B | 109.5 |
O1—C5—C4 | 115.9 (9) | H10A—C10—H10B | 109.5 |
C6—C5—C4 | 120.3 (9) | O2—C10—H10C | 109.5 |
C7—C6—C5 | 119.2 (10) | H10A—C10—H10C | 109.5 |
C7—C6—H6 | 120.4 | H10B—C10—H10C | 109.5 |
Br2—C1—C2—C3 | 0.4 (17) | O1—C5—C6—C7 | 179.4 (10) |
Br1—C1—C2—C3 | 178.7 (8) | C4—C5—C6—C7 | −0.7 (16) |
C1—C2—C3—C4 | 139.6 (11) | C10—O2—C7—C6 | −179.7 (10) |
C1—C2—C3—C8 | −44.3 (17) | C10—O2—C7—C8 | 1.2 (16) |
C8—C3—C4—C5 | 3.7 (15) | C5—C6—C7—O2 | −178.2 (9) |
C2—C3—C4—C5 | 179.9 (10) | C5—C6—C7—C8 | 0.9 (16) |
C9—O1—C5—C6 | 3.8 (16) | O2—C7—C8—C3 | −179.8 (10) |
C9—O1—C5—C4 | −176.1 (10) | C6—C7—C8—C3 | 1.2 (16) |
C3—C4—C5—O1 | 178.4 (9) | C4—C3—C8—C7 | −3.4 (15) |
C3—C4—C5—C6 | −1.6 (16) | C2—C3—C8—C7 | −179.5 (10) |