
Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052603/wn2095sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052603/wn2095Isup2.hkl |
CCDC reference: 634069
Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: maXus (Mackay et al., 1999).
C17H15BrO4S | F(000) = 800 |
Mr = 395.26 | Dx = 1.582 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 136 reflections |
a = 16.5539 (14) Å | θ = 4.1–20.6° |
b = 11.1125 (8) Å | µ = 2.62 mm−1 |
c = 9.1650 (5) Å | T = 300 K |
β = 100.098 (6)° | Irregular block, colourless |
V = 1659.8 (2) Å3 | 0.37 × 0.35 × 0.22 mm |
Z = 4 |
Bruker–Nonius KappaCCD diffractometer | 2655 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.060 |
φ scans | θmax = 26.5°, θmin = 4.5° |
Absorption correction: numerical (HABITUS; Herrendorf & Bärnighausen, 1997) | h = −19→20 |
Tmin = 0.600, Tmax = 0.805 | k = −13→13 |
17471 measured reflections | l = −10→11 |
3390 independent 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)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.025P)2 + 1.728P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
3390 reflections | Δρmax = 0.31 e Å−3 |
208 parameters | Δρmin = −0.45 e Å−3 |
0 restraints |
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 | 1.07670 (2) | 0.26706 (3) | −0.00141 (4) | 0.05410 (13) | |
S1 | 1.04563 (5) | 0.53429 (8) | 0.33347 (9) | 0.0452 (2) | |
C5 | 0.92251 (17) | 0.4182 (2) | 0.1472 (3) | 0.0338 (6) | |
C4 | 1.01047 (18) | 0.4326 (3) | 0.1929 (3) | 0.0350 (6) | |
C9 | 0.78162 (18) | 0.4973 (3) | 0.1686 (3) | 0.0394 (7) | |
H9 | 0.7850 | 0.5650 | 0.1015 | 0.047* | |
O2 | 0.73316 (15) | 0.6521 (2) | 0.3160 (3) | 0.0651 (7) | |
C6 | 0.88879 (19) | 0.3613 (3) | 0.0225 (3) | 0.0411 (7) | |
H6 | 0.9234 | 0.3319 | −0.0389 | 0.049* | |
C3 | 1.07757 (19) | 0.3798 (3) | 0.1504 (3) | 0.0384 (7) | |
C11 | 0.72925 (18) | 0.5341 (3) | 0.2772 (4) | 0.0431 (7) | |
C10 | 0.86807 (17) | 0.4675 (3) | 0.2473 (3) | 0.0395 (7) | |
H10A | 0.8930 | 0.5399 | 0.2944 | 0.047* | |
H10B | 0.8647 | 0.4092 | 0.3247 | 0.047* | |
C7 | 0.8017 (2) | 0.3431 (3) | −0.0218 (3) | 0.0442 (7) | |
C1 | 1.14510 (19) | 0.5022 (3) | 0.3307 (4) | 0.0499 (8) | |
H1 | 1.1890 | 0.5382 | 0.3925 | 0.060* | |
C2 | 1.15341 (19) | 0.4184 (3) | 0.2285 (4) | 0.0479 (8) | |
H2 | 1.2037 | 0.3894 | 0.2117 | 0.057* | |
C8 | 0.74444 (17) | 0.3904 (3) | 0.0764 (3) | 0.0377 (6) | |
H8 | 0.7340 | 0.3260 | 0.1437 | 0.045* | |
C15 | 0.6643 (2) | 0.4234 (3) | −0.0217 (4) | 0.0527 (8) | |
C13 | 0.6539 (2) | 0.5617 (4) | 0.4510 (5) | 0.0713 (11) | |
H13 | 0.6196 | 0.5475 | 0.5194 | 0.086* | |
C12 | 0.6816 (2) | 0.4759 (3) | 0.3561 (4) | 0.0584 (9) | |
H12 | 0.6688 | 0.3944 | 0.3502 | 0.070* | |
C14 | 0.6862 (2) | 0.6645 (4) | 0.4231 (5) | 0.0745 (13) | |
H14 | 0.6782 | 0.7366 | 0.4701 | 0.089* | |
O1 | 0.77427 (17) | 0.2894 (3) | −0.1356 (3) | 0.0696 (8) | |
O4 | 0.61114 (15) | 0.3346 (2) | −0.0301 (3) | 0.0681 (7) | |
O3 | 0.65141 (18) | 0.5171 (3) | −0.0838 (3) | 0.0828 (9) | |
C16 | 0.5337 (3) | 0.3510 (5) | −0.1325 (6) | 0.1015 (18) | |
H16A | 0.5041 | 0.4192 | −0.1020 | 0.122* | |
H16B | 0.5442 | 0.3663 | −0.2317 | 0.122* | |
C17 | 0.4869 (4) | 0.2452 (7) | −0.1314 (9) | 0.167 (4) | |
H17A | 0.4361 | 0.2537 | −0.1995 | 0.250* | |
H17B | 0.4757 | 0.2317 | −0.0333 | 0.250* | |
H17C | 0.5170 | 0.1781 | −0.1605 | 0.250* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0618 (2) | 0.03980 (19) | 0.0638 (2) | 0.00686 (16) | 0.01969 (16) | −0.00661 (15) |
S1 | 0.0376 (4) | 0.0607 (5) | 0.0366 (4) | −0.0040 (4) | 0.0046 (3) | −0.0089 (3) |
C5 | 0.0380 (15) | 0.0308 (14) | 0.0322 (15) | −0.0020 (12) | 0.0052 (11) | 0.0053 (11) |
C4 | 0.0399 (16) | 0.0349 (15) | 0.0304 (14) | −0.0013 (12) | 0.0066 (11) | 0.0043 (11) |
C9 | 0.0359 (16) | 0.0363 (16) | 0.0447 (17) | −0.0030 (13) | 0.0032 (13) | −0.0006 (12) |
O2 | 0.0526 (15) | 0.0535 (15) | 0.0914 (19) | −0.0051 (12) | 0.0187 (13) | −0.0244 (13) |
C6 | 0.0429 (17) | 0.0428 (17) | 0.0385 (16) | −0.0034 (14) | 0.0100 (13) | −0.0039 (13) |
C3 | 0.0451 (17) | 0.0345 (15) | 0.0367 (16) | 0.0023 (13) | 0.0103 (13) | 0.0092 (12) |
C11 | 0.0297 (15) | 0.0428 (18) | 0.0539 (19) | 0.0021 (13) | −0.0005 (13) | −0.0075 (14) |
C10 | 0.0324 (15) | 0.0479 (18) | 0.0379 (16) | −0.0053 (13) | 0.0053 (12) | −0.0078 (13) |
C7 | 0.0516 (19) | 0.0360 (17) | 0.0434 (17) | −0.0142 (14) | 0.0037 (14) | −0.0042 (13) |
C1 | 0.0342 (16) | 0.069 (2) | 0.0439 (19) | −0.0039 (16) | 0.0009 (13) | 0.0032 (16) |
C2 | 0.0366 (17) | 0.058 (2) | 0.0508 (19) | 0.0073 (15) | 0.0113 (14) | 0.0118 (16) |
C8 | 0.0372 (16) | 0.0372 (16) | 0.0362 (16) | −0.0054 (13) | 0.0002 (12) | 0.0018 (12) |
C15 | 0.0474 (19) | 0.051 (2) | 0.054 (2) | −0.0050 (17) | −0.0056 (15) | −0.0021 (16) |
C13 | 0.050 (2) | 0.092 (3) | 0.076 (3) | 0.016 (2) | 0.0239 (19) | −0.010 (2) |
C12 | 0.050 (2) | 0.056 (2) | 0.073 (2) | 0.0045 (17) | 0.0194 (18) | −0.0051 (18) |
C14 | 0.052 (2) | 0.080 (3) | 0.094 (3) | 0.007 (2) | 0.020 (2) | −0.037 (3) |
O1 | 0.0653 (17) | 0.0819 (19) | 0.0602 (16) | −0.0233 (14) | 0.0070 (13) | −0.0333 (14) |
O4 | 0.0422 (13) | 0.0675 (17) | 0.0849 (19) | −0.0155 (13) | −0.0160 (12) | 0.0061 (14) |
O3 | 0.078 (2) | 0.0591 (18) | 0.095 (2) | −0.0009 (15) | −0.0306 (16) | 0.0207 (15) |
C16 | 0.053 (3) | 0.112 (4) | 0.120 (4) | −0.013 (3) | −0.038 (3) | 0.003 (3) |
C17 | 0.081 (4) | 0.197 (8) | 0.193 (7) | −0.074 (5) | −0.058 (4) | 0.069 (6) |
Br1—C3 | 1.870 (3) | C7—C8 | 1.511 (4) |
S1—C1 | 1.689 (3) | C1—C2 | 1.345 (5) |
S1—C4 | 1.736 (3) | C1—H1 | 0.9300 |
C5—C6 | 1.339 (4) | C2—H2 | 0.9300 |
C5—C4 | 1.452 (4) | C8—C15 | 1.511 (4) |
C5—C10 | 1.498 (4) | C8—H8 | 0.9800 |
C4—C3 | 1.372 (4) | C15—O3 | 1.188 (4) |
C9—C11 | 1.488 (4) | C15—O4 | 1.315 (4) |
C9—C10 | 1.522 (4) | C13—C14 | 1.306 (6) |
C9—C8 | 1.524 (4) | C13—C12 | 1.420 (5) |
C9—H9 | 0.9800 | C13—H13 | 0.9300 |
O2—C11 | 1.357 (4) | C12—H12 | 0.9300 |
O2—C14 | 1.362 (5) | C14—H14 | 0.9300 |
C6—C7 | 1.442 (4) | O4—C16 | 1.461 (5) |
C6—H6 | 0.9300 | C16—C17 | 1.409 (7) |
C3—C2 | 1.399 (4) | C16—H16A | 0.9700 |
C11—C12 | 1.328 (5) | C16—H16B | 0.9700 |
C10—H10A | 0.9700 | C17—H17A | 0.9600 |
C10—H10B | 0.9700 | C17—H17B | 0.9600 |
C7—O1 | 1.218 (4) | C17—H17C | 0.9600 |
C1—S1—C4 | 92.98 (16) | C1—C2—C3 | 112.1 (3) |
C6—C5—C4 | 123.0 (3) | C1—C2—H2 | 123.9 |
C6—C5—C10 | 119.3 (3) | C3—C2—H2 | 123.9 |
C4—C5—C10 | 117.6 (2) | C7—C8—C15 | 107.9 (3) |
C3—C4—C5 | 133.8 (3) | C7—C8—C9 | 111.5 (2) |
C3—C4—S1 | 107.9 (2) | C15—C8—C9 | 111.6 (3) |
C5—C4—S1 | 118.4 (2) | C7—C8—H8 | 108.6 |
C11—C9—C10 | 110.6 (2) | C15—C8—H8 | 108.6 |
C11—C9—C8 | 111.1 (2) | C9—C8—H8 | 108.6 |
C10—C9—C8 | 110.4 (2) | O3—C15—O4 | 124.5 (3) |
C11—C9—H9 | 108.2 | O3—C15—C8 | 124.3 (3) |
C10—C9—H9 | 108.2 | O4—C15—C8 | 111.2 (3) |
C8—C9—H9 | 108.2 | C14—C13—C12 | 106.3 (4) |
C11—O2—C14 | 106.3 (3) | C14—C13—H13 | 126.9 |
C5—C6—C7 | 123.6 (3) | C12—C13—H13 | 126.9 |
C5—C6—H6 | 118.2 | C11—C12—C13 | 107.1 (4) |
C7—C6—H6 | 118.2 | C11—C12—H12 | 126.5 |
C4—C3—C2 | 115.0 (3) | C13—C12—H12 | 126.5 |
C4—C3—Br1 | 126.7 (2) | C13—C14—O2 | 110.9 (3) |
C2—C3—Br1 | 118.4 (2) | C13—C14—H14 | 124.5 |
C12—C11—O2 | 109.5 (3) | O2—C14—H14 | 124.5 |
C12—C11—C9 | 134.6 (3) | C15—O4—C16 | 116.6 (3) |
O2—C11—C9 | 115.8 (3) | C17—C16—O4 | 108.2 (4) |
C5—C10—C9 | 114.0 (2) | C17—C16—H16A | 110.0 |
C5—C10—H10A | 108.8 | O4—C16—H16A | 110.0 |
C9—C10—H10A | 108.8 | C17—C16—H16B | 110.0 |
C5—C10—H10B | 108.8 | O4—C16—H16B | 110.0 |
C9—C10—H10B | 108.8 | H16A—C16—H16B | 108.4 |
H10A—C10—H10B | 107.7 | C16—C17—H17A | 109.5 |
O1—C7—C6 | 120.9 (3) | C16—C17—H17B | 109.5 |
O1—C7—C8 | 120.1 (3) | H17A—C17—H17B | 109.5 |
C6—C7—C8 | 119.0 (3) | C16—C17—H17C | 109.5 |
C2—C1—S1 | 112.1 (2) | H17A—C17—H17C | 109.5 |
C2—C1—H1 | 124.0 | H17B—C17—H17C | 109.5 |
S1—C1—H1 | 124.0 |