Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015590/ci2339sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015590/ci2339Isup2.hkl |
CCDC reference: 647159
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C18H18O2S2 | F(000) = 1392 |
Mr = 330.44 | Dx = 1.296 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2yab | Cell parameters from 25 reflections |
a = 16.471 (3) Å | θ = 1.0–29.0° |
b = 9.879 (4) Å | µ = 0.32 mm−1 |
c = 22.065 (8) Å | T = 293 K |
β = 109.362 (17)° | Block, yellow |
V = 3387.2 (19) Å3 | 0.24 × 0.22 × 0.19 mm |
Z = 8 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.030 |
Radiation source: fine-focus sealed tube | θmax = 29.0°, θmin = 1.0° |
Graphite monochromator | h = 0→22 |
ω scans | k = 0→13 |
9240 measured reflections | l = −30→28 |
8931 independent reflections | 3 standard reflections every 60 min |
4621 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0896P)2 + 0.1171P] where P = (Fo2 + 2Fc2)/3 |
8931 reflections | (Δ/σ)max = 0.001 |
397 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Experimental. The IR spectrum showed a band at 1684 cm-1 due to the carbonyl group and band at 1605 cm-1 due to carbon carbon double bond. Its 1H-NMR spectrum exhibited two 6H singlets at δ 2.23 and δ 2.28 due to two S-methyl H atoms, a 3H singlet at δ 3.84 due to methoxy H atoms, and a 9H multiplet at δ 6.91–7.96 due to aromatic H atoms. Its mass spectrum showed molecular ion peak at m/z 330. |
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 | ||
S1A | 0.10263 (5) | 0.29082 (8) | 0.48121 (3) | 0.0666 (2) | |
S2A | 0.08739 (5) | 0.25045 (8) | 0.34099 (3) | 0.0663 (2) | |
O1A | 0.29582 (16) | 0.1729 (2) | 0.36310 (11) | 0.0864 (7) | |
O2A | 0.34727 (13) | 0.76805 (19) | 0.28180 (10) | 0.0700 (5) | |
C1A | 0.23768 (15) | 0.2816 (2) | 0.43549 (11) | 0.0514 (6) | |
C2A | 0.30346 (16) | 0.2865 (3) | 0.50063 (12) | 0.0558 (6) | |
C3A | 0.29992 (19) | 0.3836 (3) | 0.54528 (13) | 0.0673 (7) | |
H3A | 0.2554 | 0.4466 | 0.5345 | 0.081* | |
C4A | 0.3615 (3) | 0.3875 (4) | 0.60503 (15) | 0.0925 (12) | |
H4A | 0.3580 | 0.4516 | 0.6350 | 0.111* | |
C5A | 0.4285 (3) | 0.2959 (5) | 0.62059 (18) | 0.1089 (16) | |
H5A | 0.4705 | 0.2989 | 0.6610 | 0.131* | |
C6A | 0.4334 (2) | 0.2005 (5) | 0.5767 (2) | 0.1048 (14) | |
H6A | 0.4786 | 0.1388 | 0.5875 | 0.126* | |
C7A | 0.37103 (18) | 0.1958 (3) | 0.51647 (16) | 0.0745 (8) | |
H7A | 0.3747 | 0.1315 | 0.4867 | 0.089* | |
C8A | 0.27609 (16) | 0.2793 (3) | 0.38139 (12) | 0.0563 (6) | |
C9A | 0.29304 (14) | 0.4099 (2) | 0.35643 (11) | 0.0481 (5) | |
C10A | 0.26504 (18) | 0.5301 (3) | 0.37382 (12) | 0.0619 (7) | |
H10A | 0.2344 | 0.5292 | 0.4024 | 0.074* | |
C11A | 0.28126 (19) | 0.6513 (3) | 0.34999 (14) | 0.0657 (7) | |
H11A | 0.2616 | 0.7315 | 0.3623 | 0.079* | |
C12A | 0.32706 (15) | 0.6542 (3) | 0.30751 (12) | 0.0532 (6) | |
C13A | 0.35610 (17) | 0.5340 (3) | 0.28990 (12) | 0.0592 (6) | |
H13A | 0.3875 | 0.5350 | 0.2618 | 0.071* | |
C14A | 0.33899 (16) | 0.4148 (3) | 0.31355 (11) | 0.0539 (6) | |
H14A | 0.3583 | 0.3347 | 0.3009 | 0.065* | |
C15A | 0.3168 (2) | 0.8927 (3) | 0.29752 (17) | 0.0870 (10) | |
H15A | 0.3352 | 0.9652 | 0.2761 | 0.130* | |
H15B | 0.3395 | 0.9064 | 0.3431 | 0.130* | |
H15C | 0.2551 | 0.8911 | 0.2840 | 0.130* | |
C16A | 0.15323 (16) | 0.2774 (3) | 0.42217 (11) | 0.0528 (6) | |
C17A | 0.0373 (2) | 0.1430 (3) | 0.46781 (17) | 0.0827 (9) | |
H17A | 0.0066 | 0.1406 | 0.4980 | 0.124* | |
H17B | 0.0730 | 0.0641 | 0.4733 | 0.124* | |
H17C | −0.0031 | 0.1446 | 0.4249 | 0.124* | |
C18A | 0.0054 (2) | 0.3763 (3) | 0.32782 (16) | 0.0845 (9) | |
H18A | −0.0337 | 0.3692 | 0.2846 | 0.127* | |
H18B | 0.0313 | 0.4645 | 0.3344 | 0.127* | |
H18C | −0.0254 | 0.3627 | 0.3574 | 0.127* | |
S1B | 0.11701 (4) | 0.28229 (9) | 0.02277 (3) | 0.0697 (2) | |
S2B | 0.22673 (5) | 0.23672 (8) | 0.16264 (3) | 0.0645 (2) | |
O1B | 0.41220 (14) | 0.1525 (2) | 0.14058 (11) | 0.0829 (6) | |
O2B | 0.54948 (15) | 0.7431 (2) | 0.21339 (11) | 0.0847 (7) | |
C1B | 0.29231 (15) | 0.2643 (3) | 0.06705 (12) | 0.0529 (6) | |
C2B | 0.29988 (16) | 0.2702 (3) | 0.00176 (13) | 0.0569 (6) | |
C3B | 0.25708 (19) | 0.3657 (3) | −0.04290 (14) | 0.0681 (7) | |
H3B | 0.2221 | 0.4289 | −0.0324 | 0.082* | |
C4B | 0.2656 (2) | 0.3689 (4) | −0.10345 (15) | 0.0855 (10) | |
H4B | 0.2358 | 0.4334 | −0.1332 | 0.103* | |
C5B | 0.3172 (3) | 0.2783 (5) | −0.11936 (17) | 0.0947 (12) | |
H5B | 0.3223 | 0.2798 | −0.1601 | 0.114* | |
C6B | 0.3614 (2) | 0.1850 (4) | −0.07505 (19) | 0.0971 (12) | |
H6B | 0.3973 | 0.1236 | −0.0857 | 0.117* | |
C7B | 0.35363 (19) | 0.1804 (3) | −0.01411 (15) | 0.0722 (8) | |
H7B | 0.3846 | 0.1170 | 0.0158 | 0.087* | |
C8B | 0.37829 (16) | 0.2603 (3) | 0.12102 (12) | 0.0562 (6) | |
C9B | 0.41999 (14) | 0.3899 (2) | 0.14421 (11) | 0.0465 (5) | |
C10B | 0.38113 (16) | 0.5115 (3) | 0.12247 (11) | 0.0553 (6) | |
H10B | 0.3260 | 0.5124 | 0.0925 | 0.066* | |
C11B | 0.42191 (18) | 0.6315 (3) | 0.14404 (13) | 0.0603 (7) | |
H11B | 0.3945 | 0.7130 | 0.1288 | 0.072* | |
C12B | 0.50305 (18) | 0.6313 (3) | 0.18813 (12) | 0.0585 (7) | |
C13B | 0.54407 (17) | 0.5100 (3) | 0.21030 (12) | 0.0646 (7) | |
H13B | 0.5996 | 0.5095 | 0.2398 | 0.078* | |
C14B | 0.50270 (16) | 0.3914 (3) | 0.18863 (11) | 0.0567 (6) | |
H14B | 0.5302 | 0.3099 | 0.2038 | 0.068* | |
C15B | 0.5076 (3) | 0.8697 (4) | 0.1970 (2) | 0.1086 (14) | |
H15D | 0.5466 | 0.9410 | 0.2177 | 0.163* | |
H15E | 0.4581 | 0.8722 | 0.2108 | 0.163* | |
H15F | 0.4897 | 0.8819 | 0.1512 | 0.163* | |
C16B | 0.21969 (16) | 0.2631 (3) | 0.08147 (12) | 0.0543 (6) | |
C17B | 0.0620 (2) | 0.1377 (3) | 0.03621 (19) | 0.0901 (10) | |
H17D | 0.0043 | 0.1375 | 0.0065 | 0.135* | |
H17E | 0.0606 | 0.1395 | 0.0794 | 0.135* | |
H17F | 0.0914 | 0.0576 | 0.0301 | 0.135* | |
C18B | 0.1628 (2) | 0.3701 (3) | 0.17691 (14) | 0.0754 (8) | |
H18D | 0.1626 | 0.3647 | 0.2203 | 0.113* | |
H18E | 0.1050 | 0.3620 | 0.1477 | 0.113* | |
H18F | 0.1864 | 0.4556 | 0.1704 | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0709 (4) | 0.0752 (5) | 0.0616 (4) | −0.0159 (4) | 0.0324 (3) | −0.0068 (3) |
S2A | 0.0644 (4) | 0.0757 (5) | 0.0517 (4) | −0.0044 (4) | 0.0098 (3) | −0.0076 (3) |
O1A | 0.1219 (18) | 0.0543 (12) | 0.1049 (17) | 0.0035 (12) | 0.0670 (15) | −0.0088 (11) |
O2A | 0.0815 (13) | 0.0591 (12) | 0.0764 (13) | −0.0058 (10) | 0.0355 (11) | 0.0057 (10) |
C1A | 0.0541 (14) | 0.0483 (14) | 0.0524 (13) | −0.0056 (11) | 0.0186 (11) | 0.0017 (11) |
C2A | 0.0538 (14) | 0.0581 (15) | 0.0523 (13) | −0.0154 (12) | 0.0131 (11) | 0.0118 (12) |
C3A | 0.0750 (18) | 0.0682 (18) | 0.0535 (15) | −0.0235 (15) | 0.0144 (13) | 0.0017 (13) |
C4A | 0.105 (3) | 0.106 (3) | 0.0554 (18) | −0.053 (2) | 0.0115 (18) | 0.0016 (18) |
C5A | 0.086 (3) | 0.154 (4) | 0.064 (2) | −0.055 (3) | −0.0047 (19) | 0.035 (3) |
C6A | 0.0606 (19) | 0.138 (4) | 0.102 (3) | −0.009 (2) | 0.0081 (19) | 0.060 (3) |
C7A | 0.0574 (16) | 0.078 (2) | 0.084 (2) | −0.0063 (15) | 0.0184 (15) | 0.0215 (16) |
C8A | 0.0570 (14) | 0.0571 (16) | 0.0566 (14) | −0.0017 (12) | 0.0211 (12) | −0.0066 (12) |
C9A | 0.0477 (12) | 0.0531 (14) | 0.0443 (12) | 0.0016 (11) | 0.0166 (10) | −0.0047 (10) |
C10A | 0.0767 (17) | 0.0606 (16) | 0.0639 (15) | 0.0056 (14) | 0.0440 (14) | −0.0023 (13) |
C11A | 0.084 (2) | 0.0535 (16) | 0.0725 (18) | 0.0095 (14) | 0.0439 (16) | −0.0028 (13) |
C12A | 0.0521 (14) | 0.0574 (15) | 0.0507 (13) | −0.0026 (12) | 0.0180 (11) | −0.0005 (11) |
C13A | 0.0656 (16) | 0.0651 (17) | 0.0581 (14) | −0.0027 (13) | 0.0356 (13) | −0.0058 (13) |
C14A | 0.0565 (14) | 0.0580 (15) | 0.0528 (14) | 0.0039 (12) | 0.0255 (11) | −0.0093 (12) |
C15A | 0.099 (2) | 0.0552 (18) | 0.109 (3) | 0.0003 (17) | 0.039 (2) | 0.0082 (17) |
C16A | 0.0565 (14) | 0.0555 (15) | 0.0445 (12) | −0.0084 (12) | 0.0143 (10) | −0.0015 (11) |
C17A | 0.078 (2) | 0.075 (2) | 0.113 (3) | −0.0139 (16) | 0.0548 (19) | −0.0056 (18) |
C18A | 0.087 (2) | 0.077 (2) | 0.075 (2) | 0.0081 (17) | 0.0077 (17) | 0.0113 (16) |
S1B | 0.0556 (4) | 0.0873 (5) | 0.0617 (4) | −0.0171 (4) | 0.0135 (3) | −0.0039 (4) |
S2B | 0.0682 (4) | 0.0732 (5) | 0.0555 (4) | −0.0027 (3) | 0.0249 (3) | −0.0027 (3) |
O1B | 0.0819 (14) | 0.0517 (12) | 0.1040 (17) | 0.0081 (11) | 0.0160 (12) | 0.0036 (11) |
O2B | 0.0960 (16) | 0.0791 (15) | 0.0869 (15) | −0.0380 (13) | 0.0410 (13) | −0.0284 (12) |
C1B | 0.0526 (13) | 0.0510 (14) | 0.0555 (14) | −0.0087 (11) | 0.0184 (11) | −0.0112 (11) |
C2B | 0.0538 (13) | 0.0612 (16) | 0.0585 (14) | −0.0178 (12) | 0.0224 (12) | −0.0172 (13) |
C3B | 0.0771 (18) | 0.0663 (18) | 0.0661 (17) | −0.0112 (15) | 0.0307 (15) | −0.0067 (14) |
C4B | 0.098 (2) | 0.095 (3) | 0.0671 (19) | −0.025 (2) | 0.0318 (18) | 0.0033 (18) |
C5B | 0.105 (3) | 0.126 (3) | 0.067 (2) | −0.031 (3) | 0.046 (2) | −0.019 (2) |
C6B | 0.090 (2) | 0.120 (3) | 0.098 (3) | −0.022 (2) | 0.054 (2) | −0.048 (2) |
C7B | 0.0714 (18) | 0.0763 (19) | 0.0782 (19) | −0.0112 (15) | 0.0372 (16) | −0.0180 (16) |
C8B | 0.0568 (14) | 0.0550 (16) | 0.0604 (15) | 0.0034 (12) | 0.0244 (12) | −0.0014 (12) |
C9B | 0.0445 (12) | 0.0516 (14) | 0.0441 (12) | 0.0000 (10) | 0.0155 (10) | 0.0002 (10) |
C10B | 0.0518 (14) | 0.0548 (15) | 0.0517 (13) | 0.0029 (12) | 0.0070 (11) | −0.0007 (11) |
C11B | 0.0697 (17) | 0.0524 (16) | 0.0585 (15) | 0.0027 (13) | 0.0210 (13) | 0.0048 (12) |
C12B | 0.0679 (16) | 0.0635 (17) | 0.0525 (14) | −0.0169 (13) | 0.0313 (13) | −0.0095 (12) |
C13B | 0.0503 (14) | 0.082 (2) | 0.0539 (15) | −0.0086 (14) | 0.0076 (11) | −0.0115 (14) |
C14B | 0.0517 (14) | 0.0639 (17) | 0.0512 (14) | 0.0095 (12) | 0.0128 (11) | 0.0042 (12) |
C15B | 0.156 (4) | 0.062 (2) | 0.138 (3) | −0.039 (2) | 0.089 (3) | −0.032 (2) |
C16B | 0.0540 (13) | 0.0593 (15) | 0.0500 (13) | −0.0093 (12) | 0.0177 (11) | −0.0058 (11) |
C17B | 0.0612 (18) | 0.080 (2) | 0.123 (3) | −0.0223 (16) | 0.0229 (18) | −0.013 (2) |
C18B | 0.0768 (19) | 0.084 (2) | 0.0700 (18) | 0.0000 (16) | 0.0310 (15) | −0.0127 (16) |
S1A—C16A | 1.769 (3) | S1B—C16B | 1.767 (3) |
S1A—C17A | 1.780 (3) | S1B—C17B | 1.768 (3) |
S2A—C16A | 1.780 (2) | S2B—C16B | 1.775 (3) |
S2A—C18A | 1.786 (3) | S2B—C18B | 1.778 (3) |
O1A—C8A | 1.208 (3) | O1B—C8B | 1.214 (3) |
O2A—C12A | 1.350 (3) | O2B—C12B | 1.354 (3) |
O2A—C15A | 1.415 (4) | O2B—C15B | 1.417 (4) |
C1A—C16A | 1.323 (3) | C1B—C16B | 1.336 (3) |
C1A—C2A | 1.487 (3) | C1B—C2B | 1.488 (3) |
C1A—C8A | 1.525 (3) | C1B—C8B | 1.519 (3) |
C2A—C7A | 1.381 (4) | C2B—C7B | 1.377 (4) |
C2A—C3A | 1.390 (4) | C2B—C3B | 1.378 (4) |
C3A—C4A | 1.372 (4) | C3B—C4B | 1.389 (4) |
C3A—H3A | 0.93 | C3B—H3B | 0.93 |
C4A—C5A | 1.379 (6) | C4B—C5B | 1.358 (5) |
C4A—H4A | 0.93 | C4B—H4B | 0.93 |
C5A—C6A | 1.373 (6) | C5B—C6B | 1.365 (6) |
C5A—H5A | 0.93 | C5B—H5B | 0.93 |
C6A—C7A | 1.386 (5) | C6B—C7B | 1.393 (5) |
C6A—H6A | 0.93 | C6B—H6B | 0.93 |
C7A—H7A | 0.93 | C7B—H7B | 0.93 |
C8A—C9A | 1.465 (4) | C8B—C9B | 1.463 (3) |
C9A—C10A | 1.374 (3) | C9B—C10B | 1.371 (3) |
C9A—C14A | 1.395 (3) | C9B—C14B | 1.390 (3) |
C10A—C11A | 1.369 (4) | C10B—C11B | 1.368 (4) |
C10A—H10A | 0.93 | C10B—H10B | 0.93 |
C11A—C12A | 1.385 (3) | C11B—C12B | 1.368 (4) |
C11A—H11A | 0.93 | C11B—H11B | 0.93 |
C12A—C13A | 1.383 (4) | C12B—C13B | 1.383 (4) |
C13A—C14A | 1.355 (4) | C13B—C14B | 1.360 (4) |
C13A—H13A | 0.93 | C13B—H13B | 0.93 |
C14A—H14A | 0.93 | C14B—H14B | 0.93 |
C15A—H15A | 0.96 | C15B—H15D | 0.96 |
C15A—H15B | 0.96 | C15B—H15E | 0.96 |
C15A—H15C | 0.96 | C15B—H15F | 0.96 |
C17A—H17A | 0.96 | C17B—H17D | 0.96 |
C17A—H17B | 0.96 | C17B—H17E | 0.96 |
C17A—H17C | 0.96 | C17B—H17F | 0.96 |
C18A—H18A | 0.96 | C18B—H18D | 0.96 |
C18A—H18B | 0.96 | C18B—H18E | 0.96 |
C18A—H18C | 0.96 | C18B—H18F | 0.96 |
C16A—S1A—C17A | 102.89 (13) | C16B—S1B—C17B | 102.10 (15) |
C16A—S2A—C18A | 103.59 (14) | C16B—S2B—C18B | 103.01 (14) |
C12A—O2A—C15A | 117.7 (2) | C12B—O2B—C15B | 117.0 (3) |
C16A—C1A—C2A | 126.2 (2) | C16B—C1B—C2B | 126.9 (2) |
C16A—C1A—C8A | 120.3 (2) | C16B—C1B—C8B | 119.3 (2) |
C2A—C1A—C8A | 113.5 (2) | C2B—C1B—C8B | 113.9 (2) |
C7A—C2A—C3A | 119.2 (3) | C7B—C2B—C3B | 118.6 (3) |
C7A—C2A—C1A | 119.4 (3) | C7B—C2B—C1B | 119.2 (3) |
C3A—C2A—C1A | 121.3 (2) | C3B—C2B—C1B | 122.1 (2) |
C4A—C3A—C2A | 120.6 (3) | C2B—C3B—C4B | 120.8 (3) |
C4A—C3A—H3A | 119.7 | C2B—C3B—H3B | 119.6 |
C2A—C3A—H3A | 119.7 | C4B—C3B—H3B | 119.6 |
C3A—C4A—C5A | 119.8 (4) | C5B—C4B—C3B | 120.3 (3) |
C3A—C4A—H4A | 120.1 | C5B—C4B—H4B | 119.8 |
C5A—C4A—H4A | 120.1 | C3B—C4B—H4B | 119.8 |
C6A—C5A—C4A | 120.3 (3) | C4B—C5B—C6B | 119.4 (3) |
C6A—C5A—H5A | 119.9 | C4B—C5B—H5B | 120.3 |
C4A—C5A—H5A | 119.9 | C6B—C5B—H5B | 120.3 |
C5A—C6A—C7A | 120.1 (4) | C5B—C6B—C7B | 121.0 (3) |
C5A—C6A—H6A | 120.0 | C5B—C6B—H6B | 119.5 |
C7A—C6A—H6A | 120.0 | C7B—C6B—H6B | 119.5 |
C2A—C7A—C6A | 120.0 (4) | C2B—C7B—C6B | 119.8 (3) |
C2A—C7A—H7A | 120.0 | C2B—C7B—H7B | 120.1 |
C6A—C7A—H7A | 120.0 | C6B—C7B—H7B | 120.1 |
O1A—C8A—C9A | 122.3 (2) | O1B—C8B—C9B | 122.4 (2) |
O1A—C8A—C1A | 120.1 (2) | O1B—C8B—C1B | 120.1 (2) |
C9A—C8A—C1A | 117.5 (2) | C9B—C8B—C1B | 117.3 (2) |
C10A—C9A—C14A | 117.8 (2) | C10B—C9B—C14B | 118.2 (2) |
C10A—C9A—C8A | 122.2 (2) | C10B—C9B—C8B | 122.3 (2) |
C14A—C9A—C8A | 120.0 (2) | C14B—C9B—C8B | 119.5 (2) |
C11A—C10A—C9A | 121.5 (2) | C11B—C10B—C9B | 121.3 (2) |
C11A—C10A—H10A | 119.2 | C11B—C10B—H10B | 119.4 |
C9A—C10A—H10A | 119.2 | C9B—C10B—H10B | 119.4 |
C10A—C11A—C12A | 119.8 (2) | C12B—C11B—C10B | 119.8 (3) |
C10A—C11A—H11A | 120.1 | C12B—C11B—H11B | 120.1 |
C12A—C11A—H11A | 120.1 | C10B—C11B—H11B | 120.1 |
O2A—C12A—C13A | 116.1 (2) | O2B—C12B—C11B | 125.2 (3) |
O2A—C12A—C11A | 124.5 (2) | O2B—C12B—C13B | 114.7 (3) |
C13A—C12A—C11A | 119.3 (2) | C11B—C12B—C13B | 120.1 (2) |
C14A—C13A—C12A | 120.2 (2) | C14B—C13B—C12B | 119.5 (2) |
C14A—C13A—H13A | 119.9 | C14B—C13B—H13B | 120.2 |
C12A—C13A—H13A | 119.9 | C12B—C13B—H13B | 120.2 |
C13A—C14A—C9A | 121.4 (2) | C13B—C14B—C9B | 121.1 (2) |
C13A—C14A—H14A | 119.3 | C13B—C14B—H14B | 119.4 |
C9A—C14A—H14A | 119.3 | C9B—C14B—H14B | 119.4 |
O2A—C15A—H15A | 109.5 | O2B—C15B—H15D | 109.5 |
O2A—C15A—H15B | 109.5 | O2B—C15B—H15E | 109.5 |
H15A—C15A—H15B | 109.5 | H15D—C15B—H15E | 109.5 |
O2A—C15A—H15C | 109.5 | O2B—C15B—H15F | 109.5 |
H15A—C15A—H15C | 109.5 | H15D—C15B—H15F | 109.5 |
H15B—C15A—H15C | 109.5 | H15E—C15B—H15F | 109.5 |
C1A—C16A—S1A | 123.45 (19) | C1B—C16B—S1B | 122.6 (2) |
C1A—C16A—S2A | 118.23 (19) | C1B—C16B—S2B | 118.5 (2) |
S1A—C16A—S2A | 118.27 (14) | S1B—C16B—S2B | 118.81 (14) |
S1A—C17A—H17A | 109.5 | S1B—C17B—H17D | 109.5 |
S1A—C17A—H17B | 109.5 | S1B—C17B—H17E | 109.5 |
H17A—C17A—H17B | 109.5 | H17D—C17B—H17E | 109.5 |
S1A—C17A—H17C | 109.5 | S1B—C17B—H17F | 109.5 |
H17A—C17A—H17C | 109.5 | H17D—C17B—H17F | 109.5 |
H17B—C17A—H17C | 109.5 | H17E—C17B—H17F | 109.5 |
S2A—C18A—H18A | 109.5 | S2B—C18B—H18D | 109.5 |
S2A—C18A—H18B | 109.5 | S2B—C18B—H18E | 109.5 |
H18A—C18A—H18B | 109.5 | H18D—C18B—H18E | 109.5 |
S2A—C18A—H18C | 109.5 | S2B—C18B—H18F | 109.5 |
H18A—C18A—H18C | 109.5 | H18D—C18B—H18F | 109.5 |
H18B—C18A—H18C | 109.5 | H18E—C18B—H18F | 109.5 |
C16A—C1A—C2A—C7A | 129.3 (3) | C16B—C1B—C2B—C7B | −131.6 (3) |
C8A—C1A—C2A—C7A | −49.8 (3) | C8B—C1B—C2B—C7B | 48.8 (3) |
C16A—C1A—C2A—C3A | −52.8 (4) | C16B—C1B—C2B—C3B | 50.7 (4) |
C8A—C1A—C2A—C3A | 128.1 (3) | C8B—C1B—C2B—C3B | −128.9 (3) |
C7A—C2A—C3A—C4A | −1.7 (4) | C7B—C2B—C3B—C4B | 2.1 (4) |
C1A—C2A—C3A—C4A | −179.5 (2) | C1B—C2B—C3B—C4B | 179.8 (3) |
C2A—C3A—C4A—C5A | 1.3 (4) | C2B—C3B—C4B—C5B | −0.7 (5) |
C3A—C4A—C5A—C6A | −0.5 (5) | C3B—C4B—C5B—C6B | −0.7 (5) |
C4A—C5A—C6A—C7A | 0.1 (5) | C4B—C5B—C6B—C7B | 0.7 (6) |
C3A—C2A—C7A—C6A | 1.3 (4) | C3B—C2B—C7B—C6B | −2.1 (4) |
C1A—C2A—C7A—C6A | 179.2 (3) | C1B—C2B—C7B—C6B | −179.9 (3) |
C5A—C6A—C7A—C2A | −0.5 (5) | C5B—C6B—C7B—C2B | 0.7 (5) |
C16A—C1A—C8A—O1A | −92.0 (3) | C16B—C1B—C8B—O1B | 90.4 (3) |
C2A—C1A—C8A—O1A | 87.2 (3) | C2B—C1B—C8B—O1B | −89.9 (3) |
C16A—C1A—C8A—C9A | 92.1 (3) | C16B—C1B—C8B—C9B | −94.0 (3) |
C2A—C1A—C8A—C9A | −88.7 (3) | C2B—C1B—C8B—C9B | 85.7 (3) |
O1A—C8A—C9A—C10A | 175.2 (3) | O1B—C8B—C9B—C10B | −179.3 (3) |
C1A—C8A—C9A—C10A | −9.0 (4) | C1B—C8B—C9B—C10B | 5.2 (3) |
O1A—C8A—C9A—C14A | −4.8 (4) | O1B—C8B—C9B—C14B | 2.3 (4) |
C1A—C8A—C9A—C14A | 171.0 (2) | C1B—C8B—C9B—C14B | −173.2 (2) |
C14A—C9A—C10A—C11A | 0.1 (4) | C14B—C9B—C10B—C11B | −0.5 (4) |
C8A—C9A—C10A—C11A | −179.9 (3) | C8B—C9B—C10B—C11B | −178.9 (2) |
C9A—C10A—C11A—C12A | −0.2 (4) | C9B—C10B—C11B—C12B | 0.0 (4) |
C15A—O2A—C12A—C13A | 178.5 (3) | C15B—O2B—C12B—C11B | 5.8 (4) |
C15A—O2A—C12A—C11A | −2.4 (4) | C15B—O2B—C12B—C13B | −174.3 (3) |
C10A—C11A—C12A—O2A | −179.3 (3) | C10B—C11B—C12B—O2B | −179.4 (2) |
C10A—C11A—C12A—C13A | −0.2 (4) | C10B—C11B—C12B—C13B | 0.7 (4) |
O2A—C12A—C13A—C14A | 179.8 (2) | O2B—C12B—C13B—C14B | 179.2 (2) |
C11A—C12A—C13A—C14A | 0.7 (4) | C11B—C12B—C13B—C14B | −0.9 (4) |
C12A—C13A—C14A—C9A | −0.8 (4) | C12B—C13B—C14B—C9B | 0.4 (4) |
C10A—C9A—C14A—C13A | 0.4 (4) | C10B—C9B—C14B—C13B | 0.3 (4) |
C8A—C9A—C14A—C13A | −179.6 (2) | C8B—C9B—C14B—C13B | 178.7 (2) |
C2A—C1A—C16A—S1A | 5.3 (4) | C2B—C1B—C16B—S1B | −5.2 (4) |
C8A—C1A—C16A—S1A | −175.67 (19) | C8B—C1B—C16B—S1B | 174.36 (19) |
C2A—C1A—C16A—S2A | −172.2 (2) | C2B—C1B—C16B—S2B | 173.0 (2) |
C8A—C1A—C16A—S2A | 6.8 (3) | C8B—C1B—C16B—S2B | −7.4 (3) |
C17A—S1A—C16A—C1A | −125.5 (2) | C17B—S1B—C16B—C1B | 125.9 (3) |
C17A—S1A—C16A—S2A | 52.0 (2) | C17B—S1B—C16B—S2B | −52.4 (2) |
C18A—S2A—C16A—C1A | −133.1 (2) | C18B—S2B—C16B—C1B | 130.6 (2) |
C18A—S2A—C16A—S1A | 49.3 (2) | C18B—S2B—C16B—S1B | −51.04 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H3A···S1A | 0.93 | 2.85 | 3.218 (4) | 105 |
C3B—H3B···S1B | 0.93 | 2.82 | 3.212 (4) | 106 |
C13A—H13A···Cg1 | 0.93 | 2.78 | 3.701 (3) | 171 |