Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017634/lh6002sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017634/lh6002Isup2.hkl |
CCDC reference: 198984
Colourless single crystals of (I) were obtained as transparent needles from a saturated solution in methanol by slow evaporation at room temperature.
All H atoms were included in calculated positions with distances of 0.93 (for sp2 C—H) and 0.98 Å (for sp3 C—H). In the refinement, they were included as riding, with Uiso values equal to 1.2Ueq of the carrier atom.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
C30H22O6S | F(000) = 1064 |
Mr = 510.54 | Dx = 1.337 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 13.228 (3) Å | θ = 14–27° |
b = 11.754 (6) Å | µ = 1.50 mm−1 |
c = 18.659 (5) Å | T = 293 K |
β = 119.05 (2)° | Needle, colourless |
V = 2536.2 (16) Å3 | 0.40 × 0.34 × 0.24 mm |
Z = 4 |
Enraf-Nonius CAD-4 diffractometer | 3365 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 69.9°, θmin = 3.8° |
ω–2θ scans | h = 0→16 |
Absorption correction: ψ scan (North et al., 1968) | k = −14→0 |
Tmin = 0.576, Tmax = 0.698 | l = −22→19 |
5012 measured reflections | 2 standard reflections every 100 reflections |
4795 independent reflections | intensity decay: <1% |
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)] = 0.084 | H-atom parameters constrained |
wR(F2) = 0.221 | w = 1/[σ2(Fo2) + 14.8815P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
4795 reflections | Δρmax = 0.43 e Å−3 |
335 parameters | Δρmin = −0.45 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00103 (5) |
C30H22O6S | V = 2536.2 (16) Å3 |
Mr = 510.54 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 13.228 (3) Å | µ = 1.50 mm−1 |
b = 11.754 (6) Å | T = 293 K |
c = 18.659 (5) Å | 0.40 × 0.34 × 0.24 mm |
β = 119.05 (2)° |
Enraf-Nonius CAD-4 diffractometer | 3365 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.019 |
Tmin = 0.576, Tmax = 0.698 | 2 standard reflections every 100 reflections |
5012 measured reflections | intensity decay: <1% |
4795 independent reflections |
R[F2 > 2σ(F2)] = 0.084 | 0 restraints |
wR(F2) = 0.221 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + 14.8815P] where P = (Fo2 + 2Fc2)/3 |
4795 reflections | Δρmax = 0.43 e Å−3 |
335 parameters | Δρmin = −0.45 e Å−3 |
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 | ||
S1 | 0.34843 (13) | 0.65913 (13) | 0.61230 (9) | 0.0489 (4) | |
O1 | 0.3329 (3) | 0.7980 (4) | 0.7185 (3) | 0.0511 (10) | |
O2 | 0.5153 (4) | 0.9143 (4) | 0.7170 (3) | 0.0610 (12) | |
O3 | 0.2596 (4) | 0.5918 (4) | 0.6147 (3) | 0.0655 (13) | |
O1' | 0.3611 (4) | 0.8300 (4) | 0.5232 (3) | 0.0614 (12) | |
O2' | 0.1911 (4) | 0.9329 (4) | 0.5424 (4) | 0.0777 (15) | |
O3' | 0.4373 (4) | 0.6069 (4) | 0.6007 (3) | 0.0643 (13) | |
C1 | 0.4169 (4) | 0.7422 (5) | 0.7050 (3) | 0.0414 (13) | |
C2 | 0.3932 (5) | 0.7034 (5) | 0.7715 (4) | 0.0451 (13) | |
H2 | 0.3484 | 0.6330 | 0.7600 | 0.054* | |
C3 | 0.4710 (5) | 0.7266 (5) | 0.8579 (4) | 0.0477 (14) | |
C4 | 0.5008 (6) | 0.8379 (6) | 0.8894 (4) | 0.0564 (16) | |
H4 | 0.4728 | 0.9000 | 0.8541 | 0.068* | |
C5 | 0.5711 (6) | 0.8550 (7) | 0.9719 (4) | 0.0673 (19) | |
H5 | 0.5904 | 0.9287 | 0.9921 | 0.081* | |
C6 | 0.6135 (6) | 0.7645 (8) | 1.0253 (4) | 0.073 (2) | |
H6 | 0.6602 | 0.7766 | 1.0812 | 0.087* | |
C7 | 0.5853 (6) | 0.6553 (7) | 0.9943 (4) | 0.070 (2) | |
H7 | 0.6144 | 0.5933 | 1.0295 | 0.083* | |
C8 | 0.5156 (6) | 0.6380 (6) | 0.9128 (4) | 0.0581 (17) | |
H8 | 0.4972 | 0.5638 | 0.8934 | 0.070* | |
C9 | 0.5236 (5) | 0.8109 (5) | 0.7213 (3) | 0.0420 (13) | |
C10 | 0.6313 (5) | 0.7487 (5) | 0.7431 (3) | 0.0439 (13) | |
C11 | 0.7208 (5) | 0.8060 (6) | 0.7392 (4) | 0.0564 (16) | |
H11 | 0.7119 | 0.8819 | 0.7233 | 0.068* | |
C12 | 0.8221 (6) | 0.7499 (8) | 0.7592 (5) | 0.074 (2) | |
H12 | 0.8815 | 0.7880 | 0.7561 | 0.089* | |
C13 | 0.8369 (6) | 0.6368 (8) | 0.7839 (5) | 0.075 (2) | |
H13 | 0.9061 | 0.5998 | 0.7978 | 0.090* | |
C14 | 0.7496 (6) | 0.5800 (7) | 0.7877 (4) | 0.0668 (19) | |
H14 | 0.7594 | 0.5041 | 0.8038 | 0.080* | |
C15 | 0.6467 (5) | 0.6346 (5) | 0.7679 (4) | 0.0496 (15) | |
H15 | 0.5878 | 0.5957 | 0.7710 | 0.060* | |
C1' | 0.2779 (5) | 0.7659 (5) | 0.5325 (3) | 0.0437 (13) | |
C2' | 0.2976 (5) | 0.7468 (6) | 0.4613 (4) | 0.0562 (16) | |
H2' | 0.3405 | 0.6775 | 0.4640 | 0.067* | |
C3' | 0.2155 (6) | 0.7870 (7) | 0.3774 (4) | 0.0643 (19) | |
C4' | 0.1838 (7) | 0.8986 (8) | 0.3593 (5) | 0.085 (3) | |
H4' | 0.2110 | 0.9532 | 0.4006 | 0.102* | |
C5' | 0.1088 (8) | 0.9298 (11) | 0.2767 (7) | 0.109 (4) | |
H5' | 0.0866 | 1.0052 | 0.2630 | 0.131* | |
C6' | 0.0693 (9) | 0.8468 (14) | 0.2168 (7) | 0.121 (5) | |
H6' | 0.0212 | 0.8671 | 0.1624 | 0.145* | |
C7' | 0.0994 (8) | 0.7365 (13) | 0.2360 (6) | 0.110 (4) | |
H7' | 0.0693 | 0.6812 | 0.1953 | 0.132* | |
C8' | 0.1735 (7) | 0.7067 (9) | 0.3145 (5) | 0.084 (3) | |
H8' | 0.1967 | 0.6313 | 0.3267 | 0.101* | |
C9' | 0.1763 (5) | 0.8315 (5) | 0.5273 (4) | 0.0502 (15) | |
C10' | 0.0649 (5) | 0.7747 (5) | 0.5037 (4) | 0.0497 (14) | |
C11' | −0.0185 (6) | 0.8325 (7) | 0.5134 (4) | 0.0646 (19) | |
H11' | −0.0026 | 0.9050 | 0.5361 | 0.078* | |
C12' | −0.1249 (7) | 0.7845 (8) | 0.4900 (6) | 0.086 (3) | |
H12' | −0.1803 | 0.8243 | 0.4970 | 0.103* | |
C13' | −0.1489 (6) | 0.6763 (8) | 0.4557 (5) | 0.083 (3) | |
H13' | −0.2202 | 0.6426 | 0.4402 | 0.099* | |
C14' | −0.0667 (6) | 0.6196 (7) | 0.4452 (4) | 0.069 (2) | |
H14' | −0.0833 | 0.5472 | 0.4221 | 0.083* | |
C15' | 0.0398 (5) | 0.6670 (6) | 0.4679 (4) | 0.0567 (16) | |
H15' | 0.0942 | 0.6277 | 0.4594 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0419 (8) | 0.0425 (8) | 0.0499 (8) | −0.0008 (6) | 0.0126 (6) | −0.0018 (7) |
O1 | 0.046 (2) | 0.055 (3) | 0.056 (2) | 0.0112 (19) | 0.027 (2) | 0.003 (2) |
O2 | 0.066 (3) | 0.038 (2) | 0.083 (3) | −0.002 (2) | 0.040 (3) | 0.002 (2) |
O3 | 0.055 (3) | 0.056 (3) | 0.063 (3) | −0.018 (2) | 0.011 (2) | 0.008 (2) |
O1' | 0.048 (2) | 0.068 (3) | 0.067 (3) | −0.008 (2) | 0.027 (2) | 0.003 (2) |
O2' | 0.073 (3) | 0.045 (3) | 0.111 (4) | 0.001 (2) | 0.041 (3) | −0.010 (3) |
O3' | 0.059 (3) | 0.059 (3) | 0.063 (3) | 0.020 (2) | 0.020 (2) | −0.008 (2) |
C1 | 0.034 (3) | 0.039 (3) | 0.050 (3) | −0.001 (2) | 0.020 (2) | −0.001 (3) |
C2 | 0.040 (3) | 0.043 (3) | 0.055 (3) | −0.001 (2) | 0.025 (3) | 0.002 (3) |
C3 | 0.046 (3) | 0.058 (4) | 0.050 (3) | −0.001 (3) | 0.032 (3) | 0.005 (3) |
C4 | 0.067 (4) | 0.053 (4) | 0.057 (4) | −0.002 (3) | 0.036 (3) | 0.006 (3) |
C5 | 0.078 (5) | 0.077 (5) | 0.052 (4) | −0.014 (4) | 0.036 (4) | −0.009 (4) |
C6 | 0.068 (5) | 0.101 (6) | 0.047 (4) | −0.004 (4) | 0.026 (4) | 0.010 (4) |
C7 | 0.074 (5) | 0.076 (5) | 0.059 (4) | 0.014 (4) | 0.032 (4) | 0.016 (4) |
C8 | 0.065 (4) | 0.055 (4) | 0.061 (4) | 0.008 (3) | 0.036 (3) | 0.004 (3) |
C9 | 0.044 (3) | 0.043 (3) | 0.040 (3) | −0.004 (3) | 0.021 (3) | 0.000 (2) |
C10 | 0.035 (3) | 0.053 (3) | 0.042 (3) | −0.006 (3) | 0.017 (2) | 0.003 (3) |
C11 | 0.054 (4) | 0.061 (4) | 0.061 (4) | −0.012 (3) | 0.034 (3) | −0.001 (3) |
C12 | 0.051 (4) | 0.092 (6) | 0.091 (6) | −0.012 (4) | 0.043 (4) | −0.005 (5) |
C13 | 0.045 (4) | 0.099 (6) | 0.080 (5) | 0.015 (4) | 0.029 (4) | 0.001 (5) |
C14 | 0.055 (4) | 0.069 (5) | 0.073 (5) | 0.014 (4) | 0.029 (4) | 0.013 (4) |
C15 | 0.044 (3) | 0.048 (3) | 0.053 (4) | 0.003 (3) | 0.021 (3) | 0.007 (3) |
C1' | 0.037 (3) | 0.045 (3) | 0.046 (3) | −0.008 (2) | 0.017 (2) | 0.000 (3) |
C2' | 0.045 (3) | 0.071 (4) | 0.052 (4) | −0.004 (3) | 0.023 (3) | −0.004 (3) |
C3' | 0.050 (4) | 0.093 (6) | 0.059 (4) | −0.008 (4) | 0.035 (3) | 0.011 (4) |
C4' | 0.057 (4) | 0.099 (7) | 0.088 (6) | −0.015 (4) | 0.027 (4) | 0.024 (5) |
C5' | 0.073 (6) | 0.131 (9) | 0.115 (8) | −0.007 (6) | 0.039 (6) | 0.060 (8) |
C6' | 0.075 (7) | 0.196 (15) | 0.089 (8) | −0.006 (8) | 0.038 (6) | 0.054 (9) |
C7' | 0.082 (6) | 0.187 (13) | 0.065 (6) | −0.008 (8) | 0.038 (5) | −0.003 (7) |
C8' | 0.068 (5) | 0.124 (8) | 0.061 (5) | 0.006 (5) | 0.032 (4) | −0.006 (5) |
C9' | 0.053 (4) | 0.040 (3) | 0.056 (4) | 0.002 (3) | 0.026 (3) | −0.005 (3) |
C10' | 0.041 (3) | 0.053 (4) | 0.051 (3) | 0.006 (3) | 0.019 (3) | 0.009 (3) |
C11' | 0.058 (4) | 0.066 (5) | 0.072 (5) | 0.021 (4) | 0.033 (4) | 0.021 (4) |
C12' | 0.058 (5) | 0.103 (7) | 0.112 (7) | 0.024 (5) | 0.052 (5) | 0.036 (6) |
C13' | 0.042 (4) | 0.095 (7) | 0.101 (6) | −0.005 (4) | 0.026 (4) | 0.034 (5) |
C14' | 0.047 (4) | 0.069 (5) | 0.073 (5) | −0.007 (3) | 0.014 (3) | 0.014 (4) |
C15' | 0.045 (3) | 0.053 (4) | 0.062 (4) | −0.002 (3) | 0.018 (3) | −0.002 (3) |
S1—O3' | 1.432 (4) | C13—C14 | 1.366 (10) |
S1—O3 | 1.435 (4) | C13—H13 | 0.9300 |
S1—C1 | 1.801 (6) | C14—C15 | 1.383 (8) |
S1—C1' | 1.820 (6) | C14—H14 | 0.9300 |
O1—C1 | 1.414 (6) | C15—H15 | 0.9300 |
O1—C2 | 1.443 (7) | C1'—C2' | 1.490 (8) |
O2—C9 | 1.220 (7) | C1'—C9' | 1.511 (8) |
O1'—C1' | 1.413 (7) | C2'—C3' | 1.484 (9) |
O1'—C2' | 1.433 (8) | C2'—H2' | 0.9800 |
O2'—C9' | 1.218 (7) | C3'—C4' | 1.369 (11) |
C1—C2 | 1.490 (8) | C3'—C8' | 1.394 (11) |
C1—C9 | 1.523 (7) | C4'—C5' | 1.417 (12) |
C2—C3 | 1.457 (8) | C4'—H4' | 0.9300 |
C2—H2 | 0.9800 | C5'—C6' | 1.381 (16) |
C3—C8 | 1.376 (9) | C5'—H5' | 0.9300 |
C3—C4 | 1.410 (9) | C6'—C7' | 1.352 (16) |
C4—C5 | 1.374 (9) | C6'—H6' | 0.9300 |
C4—H4 | 0.9300 | C7'—C8' | 1.355 (12) |
C5—C6 | 1.376 (10) | C7'—H7' | 0.9300 |
C5—H5 | 0.9300 | C8'—H8' | 0.9300 |
C6—C7 | 1.383 (11) | C9'—C10' | 1.476 (8) |
C6—H6 | 0.9300 | C10'—C11' | 1.381 (8) |
C7—C8 | 1.357 (9) | C10'—C15' | 1.394 (9) |
C7—H7 | 0.9300 | C11'—C12' | 1.374 (10) |
C8—H8 | 0.9300 | C11'—H11' | 0.9300 |
C9—C10 | 1.472 (8) | C12'—C13' | 1.390 (12) |
C10—C11 | 1.393 (8) | C12'—H12' | 0.9300 |
C10—C15 | 1.401 (8) | C13'—C14' | 1.368 (11) |
C11—C12 | 1.373 (10) | C13'—H13' | 0.9300 |
C11—H11 | 0.9300 | C14'—C15' | 1.377 (9) |
C12—C13 | 1.389 (11) | C14'—H14' | 0.9300 |
C12—H12 | 0.9300 | C15'—H15' | 0.9300 |
C4···O3'i | 3.25 (1) | C14···O1iii | 3.47 (1) |
C5···O3'i | 3.24 (1) | C7'···O1v | 3.29 (1) |
C7···O1'ii | 3.27 (1) | C8'···O1v | 3.37 (1) |
C8···O2iii | 3.46 (1) | C14'···C12vi | 3.41 (1) |
C12···C14'iv | 3.41 (1) | ||
O3'—S1—O3 | 120.8 (3) | C15—C14—H14 | 119.8 |
O3'—S1—C1 | 108.1 (3) | C14—C15—C10 | 119.9 (6) |
O3—S1—C1 | 107.9 (3) | C14—C15—H15 | 120.0 |
O3'—S1—C1' | 107.7 (3) | C10—C15—H15 | 120.0 |
O3—S1—C1' | 107.7 (3) | O1'—C1'—C2' | 59.1 (4) |
C1—S1—C1' | 103.3 (3) | O1'—C1'—C9' | 116.2 (5) |
C1—O1—C2 | 62.9 (3) | C2'—C1'—C9' | 123.7 (5) |
C1'—O1'—C2' | 63.1 (4) | O1'—C1'—S1 | 110.3 (4) |
O1—C1—C2 | 59.5 (3) | C2'—C1'—S1 | 112.5 (4) |
O1—C1—C9 | 116.8 (5) | C9'—C1'—S1 | 119.5 (4) |
C2—C1—C9 | 123.0 (5) | O1'—C2'—C3' | 118.3 (6) |
O1—C1—S1 | 110.5 (4) | O1'—C2'—C1' | 57.8 (4) |
C2—C1—S1 | 115.0 (4) | C3'—C2'—C1' | 122.5 (6) |
C9—C1—S1 | 117.7 (4) | O1'—C2'—H2' | 115.3 |
O1—C2—C3 | 118.2 (5) | C3'—C2'—H2' | 115.3 |
O1—C2—C1 | 57.6 (3) | C1'—C2'—H2' | 115.3 |
C3—C2—C1 | 122.9 (5) | C4'—C3'—C8' | 119.5 (8) |
O1—C2—H2 | 115.3 | C4'—C3'—C2' | 123.0 (8) |
C3—C2—H2 | 115.3 | C8'—C3'—C2' | 117.4 (8) |
C1—C2—H2 | 115.3 | C3'—C4'—C5' | 119.0 (10) |
C8—C3—C4 | 117.4 (6) | C3'—C4'—H4' | 120.5 |
C8—C3—C2 | 120.0 (6) | C5'—C4'—H4' | 120.5 |
C4—C3—C2 | 122.6 (6) | C6'—C5'—C4' | 119.2 (11) |
C5—C4—C3 | 120.2 (6) | C6'—C5'—H5' | 120.4 |
C5—C4—H4 | 119.9 | C4'—C5'—H5' | 120.4 |
C3—C4—H4 | 119.9 | C7'—C6'—C5' | 121.0 (11) |
C4—C5—C6 | 121.0 (7) | C7'—C6'—H6' | 119.5 |
C4—C5—H5 | 119.5 | C5'—C6'—H6' | 119.5 |
C6—C5—H5 | 119.5 | C6'—C7'—C8' | 120.0 (12) |
C5—C6—C7 | 118.9 (7) | C6'—C7'—H7' | 120.0 |
C5—C6—H6 | 120.6 | C8'—C7'—H7' | 120.0 |
C7—C6—H6 | 120.6 | C7'—C8'—C3' | 121.3 (10) |
C8—C7—C6 | 120.4 (7) | C7'—C8'—H8' | 119.4 |
C8—C7—H7 | 119.8 | C3'—C8'—H8' | 119.4 |
C6—C7—H7 | 119.8 | O2'—C9'—C10' | 122.5 (6) |
C7—C8—C3 | 122.2 (7) | O2'—C9'—C1' | 116.5 (6) |
C7—C8—H8 | 118.9 | C10'—C9'—C1' | 121.0 (5) |
C3—C8—H8 | 118.9 | C11'—C10'—C15' | 119.3 (6) |
O2—C9—C10 | 123.9 (5) | C11'—C10'—C9' | 118.9 (6) |
O2—C9—C1 | 118.0 (5) | C15'—C10'—C9' | 121.7 (6) |
C10—C9—C1 | 118.1 (5) | C12'—C11'—C10' | 121.1 (8) |
C11—C10—C15 | 119.3 (6) | C12'—C11'—H11' | 119.4 |
C11—C10—C9 | 118.6 (6) | C10'—C11'—H11' | 119.4 |
C15—C10—C9 | 122.1 (5) | C11'—C12'—C13' | 119.5 (8) |
C12—C11—C10 | 119.7 (7) | C11'—C12'—H12' | 120.3 |
C12—C11—H11 | 120.2 | C13'—C12'—H12' | 120.3 |
C10—C11—H11 | 120.2 | C14'—C13'—C12' | 119.4 (7) |
C11—C12—C13 | 120.8 (7) | C14'—C13'—H13' | 120.3 |
C11—C12—H12 | 119.6 | C12'—C13'—H13' | 120.3 |
C13—C12—H12 | 119.6 | C13'—C14'—C15' | 121.7 (8) |
C14—C13—C12 | 119.9 (7) | C13'—C14'—H14' | 119.2 |
C14—C13—H13 | 120.0 | C15'—C14'—H14' | 119.2 |
C12—C13—H13 | 120.0 | C14'—C15'—C10' | 119.0 (7) |
C13—C14—C15 | 120.4 (7) | C14'—C15'—H15' | 120.5 |
C13—C14—H14 | 119.8 | C10'—C15'—H15' | 120.5 |
C2—O1—C1—C9 | −114.3 (6) | C2'—O1'—C1'—C9' | −115.2 (6) |
C2—O1—C1—S1 | 107.6 (4) | C2'—O1'—C1'—S1 | 104.7 (5) |
O3'—S1—C1—O1 | 178.7 (4) | O3'—S1—C1'—O1' | −44.1 (5) |
O3—S1—C1—O1 | −49.2 (4) | O3—S1—C1'—O1' | −175.9 (4) |
C1'—S1—C1—O1 | 64.7 (4) | C1—S1—C1'—O1' | 70.1 (4) |
O3'—S1—C1—C2 | −116.4 (4) | O3'—S1—C1'—C2' | 19.9 (5) |
O3—S1—C1—C2 | 15.8 (5) | O3—S1—C1'—C2' | −111.9 (4) |
C1'—S1—C1—C2 | 129.6 (4) | C1—S1—C1'—C2' | 134.1 (4) |
O3'—S1—C1—C9 | 41.0 (5) | O3'—S1—C1'—C9' | 177.3 (4) |
O3—S1—C1—C9 | 173.1 (4) | O3—S1—C1'—C9' | 45.5 (5) |
C1'—S1—C1—C9 | −73.0 (5) | C1—S1—C1'—C9' | −68.4 (5) |
C1—O1—C2—C3 | 113.0 (6) | C1'—O1'—C2'—C3' | 112.4 (6) |
C9—C1—C2—O1 | 104.0 (6) | C9'—C1'—C2'—O1' | 102.6 (6) |
S1—C1—C2—O1 | −100.0 (4) | S1—C1'—C2'—O1' | −101.0 (4) |
O1—C1—C2—C3 | −104.8 (6) | O1'—C1'—C2'—C3' | −105.3 (7) |
C9—C1—C2—C3 | −0.8 (9) | C9'—C1'—C2'—C3' | −2.7 (10) |
S1—C1—C2—C3 | 155.2 (5) | S1—C1'—C2'—C3' | 153.7 (6) |
O1—C2—C3—C8 | 169.5 (5) | O1'—C2'—C3'—C4' | −10.7 (10) |
C1—C2—C3—C8 | −122.6 (6) | C1'—C2'—C3'—C4' | 57.2 (10) |
O1—C2—C3—C4 | −8.4 (8) | O1'—C2'—C3'—C8' | 166.5 (6) |
C1—C2—C3—C4 | 59.4 (8) | C1'—C2'—C3'—C8' | −125.5 (7) |
C8—C3—C4—C5 | −0.4 (9) | C8'—C3'—C4'—C5' | 0.0 (11) |
C2—C3—C4—C5 | 177.6 (6) | C2'—C3'—C4'—C5' | 177.2 (7) |
C3—C4—C5—C6 | −0.1 (11) | C3'—C4'—C5'—C6' | 0.3 (13) |
C4—C5—C6—C7 | 0.8 (11) | C4'—C5'—C6'—C7' | 1.1 (16) |
C5—C6—C7—C8 | −1.1 (12) | C5'—C6'—C7'—C8' | −2.9 (17) |
C6—C7—C8—C3 | 0.6 (11) | C6'—C7'—C8'—C3' | 3.2 (14) |
C4—C3—C8—C7 | 0.2 (10) | C4'—C3'—C8'—C7' | −1.8 (12) |
C2—C3—C8—C7 | −177.8 (6) | C2'—C3'—C8'—C7' | −179.1 (7) |
O1—C1—C9—O2 | −24.7 (8) | O1'—C1'—C9'—O2' | −23.3 (8) |
C2—C1—C9—O2 | −94.3 (7) | C2'—C1'—C9'—O2' | −92.2 (8) |
S1—C1—C9—O2 | 110.3 (6) | S1—C1'—C9'—O2' | 113.0 (6) |
O1—C1—C9—C10 | 154.0 (5) | O1'—C1'—C9'—C10' | 155.8 (5) |
C2—C1—C9—C10 | 84.5 (7) | C2'—C1'—C9'—C10' | 86.9 (8) |
S1—C1—C9—C10 | −70.9 (6) | S1—C1'—C9'—C10' | −67.9 (7) |
O2—C9—C10—C11 | −16.3 (9) | O2'—C9'—C10'—C11' | −12.2 (10) |
C1—C9—C10—C11 | 165.1 (5) | C1'—C9'—C10'—C11' | 168.8 (6) |
O2—C9—C10—C15 | 163.3 (6) | O2'—C9'—C10'—C15' | 164.3 (7) |
C1—C9—C10—C15 | −15.4 (8) | C1'—C9'—C10'—C15' | −14.7 (9) |
C15—C10—C11—C12 | 0.5 (10) | C15'—C10'—C11'—C12' | 1.4 (10) |
C9—C10—C11—C12 | −180.0 (6) | C9'—C10'—C11'—C12' | 178.0 (7) |
C10—C11—C12—C13 | −0.6 (11) | C10'—C11'—C12'—C13' | −0.2 (12) |
C11—C12—C13—C14 | 0.6 (13) | C11'—C12'—C13'—C14' | −0.6 (12) |
C12—C13—C14—C15 | −0.6 (12) | C12'—C13'—C14'—C15' | 0.2 (12) |
C13—C14—C15—C10 | 0.5 (11) | C13'—C14'—C15'—C10' | 1.0 (11) |
C11—C10—C15—C14 | −0.4 (9) | C11'—C10'—C15'—C14' | −1.8 (10) |
C9—C10—C15—C14 | −179.9 (6) | C9'—C10'—C15'—C14' | −178.3 (6) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) x+1, −y+3/2, z+1/2; (v) x, −y+3/2, z−1/2; (vi) x−1, −y+3/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O2iii | 0.93 | 2.60 | 3.458 (8) | 154 |
Symmetry code: (iii) −x+1, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C30H22O6S |
Mr | 510.54 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.228 (3), 11.754 (6), 18.659 (5) |
β (°) | 119.05 (2) |
V (Å3) | 2536.2 (16) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.50 |
Crystal size (mm) | 0.40 × 0.34 × 0.24 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.576, 0.698 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5012, 4795, 3365 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.084, 0.221, 1.12 |
No. of reflections | 4795 |
No. of parameters | 335 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + 14.8815P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.43, −0.45 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1999), SHELXL97.
C4···O3'i | 3.25 (1) | C14···O1iii | 3.47 (1) |
C5···O3'i | 3.24 (1) | C7'···O1v | 3.29 (1) |
C7···O1'ii | 3.27 (1) | C8'···O1v | 3.37 (1) |
C8···O2iii | 3.46 (1) | C14'···C12vi | 3.41 (1) |
C12···C14'iv | 3.41 (1) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) x+1, −y+3/2, z+1/2; (v) x, −y+3/2, z−1/2; (vi) x−1, −y+3/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O2iii | 0.93 | 2.60 | 3.458 (8) | 154 |
Symmetry code: (iii) −x+1, y−1/2, −z+3/2. |
Organic synthesis of small ring heterocycles, such as oxiranes, assume great importance in view of their reactivity towards a host of reagents and the synthetic potential associated with them. Details of chemical synthesis, NMR studies and preliminary crystallographic data for the title compound, (I), have already been reported (Renuga et al., 1999). Interestingly, the (I) exhibits stereoisomerism and the difficulty in ascertaining the configuration arises because one of the C atoms of each oxirane ring is a chiral center, as a result of which the molecule further exhibits diastereoisomerism with respect to the oxirane rings. Recently, the crystal structure of 2.2'-thiobis[2-benzoyl-3-(4-chlorophenyl)oxirane] (Krishnakumar et al., 2002) was elucidated in our laboratory.
Fig. 1 shows the atom-numbering scheme adopted for (I). This study demonstrates the relative configuration between the aryl and aroyl groups (cis) on one hand and that between the two oxirane rings (cis) on the other. The configuration of (I), which is symmetrical in solution in the absence of intermolecular interactions, assumes an unsymmetrical configuration in the solid state. The absence of symmetry is probably necessitated by the optimum packing considerations which bring different oxirane molecules in proximity, unlike in solution.
Fig. 2 shows the arrangement of molecules in layers parallel to the (020) plane, viewed down the a axis. The packing features of (I) are distinctly different from those of the 2.2'-thiobis[2-benzoyl-3-(4-chlrophenyl)oxirane], as its packing is determined, not only by the C—H···O, but also by the Cl···Cl interactions. The molecules of (I) do not directly interact among themselves, except for the presence of a C—H···O hydrogen bond. In addition, the structure is stablized by a number of C···O short contacts (see Table 1). Since the molecules of (I) have aromatic rings, C—H···π interactions are expected to play a dominent role in stablizing the crystal packing. An investigation (Malone et al., 1997) on the nature of C—H···π interactions using the Cambridge Structural Database (Allen & Kennard, 1993) and theoretical calculations suggest six possible forms of interactions between an H atom and an aromatic ring. A recent database study (Umezawa et al., 1998) on the nature of C—H···π interactions shows that these interactions also contribute sufficiently to the optimum packing modes observed in the crystal structures of organic compounds. The observed H···π distances are 3.002 and 3.003 Å (below a cut off value of 3.05 Å), with C—H···π angles 158 and 133°.