Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502979X/bt6742sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680502979X/bt67422sup2.hkl |
CCDC reference: 289645
Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
C20H20S2 | Z = 4 |
Mr = 324.48 | F(000) = 688 |
Triclinic, P1 | Dx = 1.379 Mg m−3 |
a = 10.088 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.182 (2) Å | Cell parameters from 52 reflections |
c = 15.247 (2) Å | θ = 10–11.5° |
α = 86.53 (2)° | µ = 0.33 mm−1 |
β = 88.44 (2)° | T = 143 K |
γ = 89.81 (2)° | Prism, colourless |
V = 1562.7 (5) Å3 | 0.6 × 0.35 × 0.3 mm |
Stoe STADI-4 diffractometer | Rint = 0.026 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 3.1° |
Graphite monochromator | h = −12→6 |
θ/ω scans | k = −12→12 |
9570 measured reflections | l = −18→18 |
5496 independent reflections | 3 standard reflections every 60 min |
4469 reflections with I > 2σ(I) | intensity decay: 2% |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0354P)2 + 1.5793P] where P = (Fo2 + 2Fc2)/3 |
5496 reflections | (Δ/σ)max < 0.001 |
397 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.38 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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 8.2417 (0.0082) x + 5.8422 (0.0102) y - 0.3478 (0.0216) z = 5.6479 (0.0045) * 0.0027 (0.0011) C4 * -0.0027 (0.0011) C5 * 0.0027 (0.0011) C7 * -0.0027 (0.0011) C8 - 0.1586 (0.0035) C3 - 0.1542 (0.0034) C6 Rms deviation of fitted atoms = 0.0027 8.2191 (0.0066) x + 5.8387 (0.0079) y - 0.6877 (0.0161) z = 5.6250 (0.0033) Angle to previous plane (with approximate e.s.d.) = 1.28 (0.15) * -0.0121 (0.0016) C4 * 0.0081 (0.0015) C5 * 0.0094 (0.0014) C17 * -0.0010 (0.0014) C18 * -0.0044 (0.0012) S1 Rms deviation of fitted atoms = 0.0080 6.2896 (0.0095) x + 7.7161 (0.0099) y - 2.0906 (0.0215) z = 4.4340 (0.0126) Angle to previous plane (with approximate e.s.d.) = 16.31 (0.14) * 0.0017 (0.0012) C4' * -0.0017 (0.0012) C5' * 0.0017 (0.0012) C7' * -0.0017 (0.0012) C8' 0.1581 (0.0035) C3' 0.1519 (0.0035) C6' Rms deviation of fitted atoms = 0.0017 6.2499 (0.0075) x + 7.7221 (0.0076) y - 2.2399 (0.0160) z = 4.3489 (0.0087) Angle to previous plane (with approximate e.s.d.) = 0.60 (0.17) * 0.0006 (0.0016) C4' * 0.0049 (0.0016) C5' * -0.0047 (0.0014) C17' * -0.0069 (0.0014) C18' * 0.0061 (0.0012) S1' Rms deviation of fitted atoms = 0.0051 - 8.0582 (0.0085) x + 6.0346 (0.0100) y + 1.5430 (0.0213) z = 1.4871 (0.0051) Angle to previous plane (with approximate e.s.d.) = 86.39 (0.07) * -0.0045 (0.0011) C4" * 0.0045 (0.0011) C5" * -0.0045 (0.0011) C7" * 0.0045 (0.0011) C8" 0.1614 (0.0033) C3" 0.1571 (0.0034) C6" Rms deviation of fitted atoms = 0.0045 - 8.0939 (0.0068) x + 5.9333 (0.0079) y + 1.9841 (0.0166) z = 1.4685 (0.0030) Angle to previous plane (with approximate e.s.d.) = 1.81 (0.16) * 0.0036 (0.0016) C4" * -0.0105 (0.0015) C5" * 0.0036 (0.0014) C17" * 0.0110 (0.0014) C18" * -0.0077 (0.0012) S1" Rms deviation of fitted atoms = 0.0080 5.5183 (0.0107) x - 8.5054 (0.0076) y - 0.6510 (0.0211) z = 3.6608 (0.0185) Angle to previous plane (with approximate e.s.d.) = 21.62 (0.13) * -0.0031 (0.0011) C4* * 0.0031 (0.0011) C5* * -0.0031 (0.0011) C7* * 0.0031 (0.0011) C8* 0.1622 (0.0034) C3* 0.1588 (0.0034) C6* Rms deviation of fitted atoms = 0.0031 5.5258 (0.0084) x - 8.4981 (0.0063) y - 0.2217 (0.0163) z = 3.9049 (0.0137) Angle to previous plane (with approximate e.s.d.) = 1.61 (0.15) * 0.0103 (0.0016) C4* * -0.0138 (0.0015) C5* * -0.0024 (0.0014) C17* * 0.0099 (0.0013) C18* * -0.0039 (0.0012) S1* Rms deviation of fitted atoms = 0.0091 |
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 | 0.46742 (7) | 0.32035 (7) | 0.13319 (5) | 0.04091 (19) | |
C2 | 0.6735 (3) | −0.1030 (3) | 0.13715 (17) | 0.0384 (6) | |
H2A | 0.7013 | −0.0607 | 0.1904 | 0.046* | |
H2B | 0.7408 | −0.1703 | 0.1235 | 0.046* | |
C3 | 0.6690 (2) | −0.0005 (2) | 0.06142 (16) | 0.0272 (5) | |
C4 | 0.6035 (2) | 0.1200 (2) | 0.06956 (15) | 0.0254 (5) | |
C5 | 0.5516 (2) | 0.1879 (2) | −0.00326 (15) | 0.0251 (5) | |
C6 | 0.5648 (2) | 0.1384 (2) | −0.08687 (15) | 0.0275 (5) | |
C7 | 0.6555 (2) | 0.0368 (2) | −0.09597 (16) | 0.0298 (5) | |
H7 | 0.6831 | 0.0138 | −0.1531 | 0.036* | |
C8 | 0.7063 (2) | −0.0315 (2) | −0.02310 (16) | 0.0290 (5) | |
H8 | 0.7679 | −0.1009 | −0.0311 | 0.035* | |
C9 | 0.4655 (3) | 0.1730 (3) | −0.15685 (16) | 0.0387 (6) | |
H9A | 0.5017 | 0.1468 | −0.2142 | 0.046* | |
H9B | 0.4522 | 0.2695 | −0.1612 | 0.046* | |
C17 | 0.5727 (3) | 0.1773 (2) | 0.15669 (16) | 0.0327 (6) | |
H17A | 0.6554 | 0.2037 | 0.1844 | 0.039* | |
H17B | 0.5259 | 0.1120 | 0.1970 | 0.039* | |
C18 | 0.4681 (3) | 0.3061 (2) | 0.01518 (16) | 0.0318 (6) | |
H18A | 0.3766 | 0.2944 | −0.0050 | 0.038* | |
H18B | 0.5061 | 0.3863 | −0.0156 | 0.038* | |
S1' | 0.16487 (7) | 0.53926 (7) | 0.37484 (4) | 0.04050 (19) | |
C2' | 0.3479 (3) | 0.5699 (3) | 0.65659 (16) | 0.0382 (6) | |
H2'1 | 0.3785 | 0.5411 | 0.7158 | 0.046* | |
H2'2 | 0.2524 | 0.5917 | 0.6619 | 0.046* | |
C3' | 0.3662 (2) | 0.4581 (2) | 0.59600 (15) | 0.0282 (5) | |
C4' | 0.3074 (2) | 0.4634 (2) | 0.51371 (15) | 0.0250 (5) | |
C5' | 0.3636 (2) | 0.3986 (2) | 0.44486 (15) | 0.0251 (5) | |
C6' | 0.4808 (2) | 0.3258 (2) | 0.45561 (16) | 0.0280 (5) | |
C7' | 0.5197 (2) | 0.2980 (2) | 0.54149 (17) | 0.0305 (6) | |
H7' | 0.5863 | 0.2336 | 0.5530 | 0.037* | |
C8' | 0.4627 (3) | 0.3627 (2) | 0.61063 (16) | 0.0317 (6) | |
H8' | 0.4902 | 0.3413 | 0.6689 | 0.038* | |
C9' | 0.5725 (3) | 0.3027 (3) | 0.37834 (18) | 0.0374 (6) | |
H9'1 | 0.5198 | 0.2713 | 0.3300 | 0.045* | |
H9'2 | 0.6365 | 0.2326 | 0.3957 | 0.045* | |
C17' | 0.1912 (2) | 0.5504 (3) | 0.49131 (16) | 0.0322 (6) | |
H17C | 0.2101 | 0.6424 | 0.5044 | 0.039* | |
H17D | 0.1113 | 0.5203 | 0.5260 | 0.039* | |
C18' | 0.2994 (3) | 0.4236 (3) | 0.35732 (16) | 0.0323 (6) | |
H18C | 0.2647 | 0.3406 | 0.3364 | 0.039* | |
H18D | 0.3644 | 0.4613 | 0.3130 | 0.039* | |
S1" | −0.02945 (8) | 0.15950 (8) | 0.13919 (5) | 0.0492 (2) | |
C2" | 0.1827 (3) | 0.5802 (3) | 0.13048 (17) | 0.0345 (6) | |
H2"1 | 0.2506 | 0.6478 | 0.1136 | 0.041* | |
H2"2 | 0.2129 | 0.5297 | 0.1838 | 0.041* | |
C3" | 0.1718 (2) | 0.4881 (2) | 0.05693 (15) | 0.0261 (5) | |
C4" | 0.1046 (2) | 0.3677 (2) | 0.06925 (15) | 0.0249 (5) | |
C5" | 0.0478 (2) | 0.3112 (2) | −0.00086 (15) | 0.0257 (5) | |
C6" | 0.0577 (2) | 0.3714 (2) | −0.08575 (15) | 0.0269 (5) | |
C7" | 0.1503 (2) | 0.4717 (2) | −0.09934 (16) | 0.0289 (5) | |
H7" | 0.1758 | 0.5012 | −0.1576 | 0.035* | |
C8" | 0.2058 (2) | 0.5295 (2) | −0.02908 (16) | 0.0285 (5) | |
H8" | 0.2683 | 0.5986 | −0.0400 | 0.034* | |
C9" | −0.0465 (3) | 0.3486 (3) | −0.15289 (17) | 0.0367 (6) | |
H9"1 | −0.0621 | 0.2529 | −0.1549 | 0.044* | |
H9"2 | −0.0132 | 0.3820 | −0.2117 | 0.044* | |
C17" | 0.0765 (3) | 0.2995 (3) | 0.15819 (17) | 0.0371 (6) | |
H17E | 0.0307 | 0.3600 | 0.1976 | 0.045* | |
H17F | 0.1600 | 0.2693 | 0.1855 | 0.045* | |
C18" | −0.0368 (3) | 0.1919 (2) | 0.02156 (17) | 0.0335 (6) | |
H18E | −0.0025 | 0.1156 | −0.0094 | 0.040* | |
H18F | −0.1294 | 0.2089 | 0.0041 | 0.040* | |
S1* | 0.68145 (8) | −0.03311 (8) | 0.65854 (5) | 0.0496 (2) | |
C2* | 1.1154 (3) | 0.1545 (3) | 0.63405 (17) | 0.0354 (6) | |
H2*1 | 1.0766 | 0.1763 | 0.6917 | 0.043* | |
H2*2 | 1.1844 | 0.2209 | 0.6169 | 0.043* | |
C3* | 1.0081 (2) | 0.1613 (2) | 0.56640 (16) | 0.0277 (5) | |
C4* | 0.8851 (2) | 0.0996 (2) | 0.58273 (15) | 0.0252 (5) | |
C5* | 0.8128 (2) | 0.0572 (2) | 0.51405 (15) | 0.0249 (5) | |
C6* | 0.8598 (2) | 0.0761 (2) | 0.42674 (15) | 0.0262 (5) | |
C7* | 0.9640 (2) | 0.1639 (2) | 0.41142 (16) | 0.0290 (5) | |
H7* | 0.9855 | 0.1960 | 0.3530 | 0.035* | |
C8* | 1.0372 (2) | 0.2054 (2) | 0.48019 (16) | 0.0277 (5) | |
H8* | 1.1085 | 0.2651 | 0.4681 | 0.033* | |
C9* | 0.8179 (3) | −0.0129 (3) | 0.35679 (16) | 0.0333 (6) | |
H9*1 | 0.8418 | 0.0290 | 0.2982 | 0.040* | |
H9*2 | 0.7203 | −0.0230 | 0.3603 | 0.040* | |
C17* | 0.8300 (3) | 0.0629 (3) | 0.67342 (16) | 0.0355 (6) | |
H17G | 0.8079 | 0.1428 | 0.7048 | 0.043* | |
H17H | 0.8953 | 0.0102 | 0.7079 | 0.043* | |
C18* | 0.6925 (2) | −0.0244 (2) | 0.53958 (16) | 0.0313 (6) | |
H18G | 0.7020 | −0.1137 | 0.5177 | 0.038* | |
H18H | 0.6119 | 0.0171 | 0.5146 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0449 (4) | 0.0421 (4) | 0.0372 (4) | 0.0133 (3) | 0.0002 (3) | −0.0154 (3) |
C2 | 0.0445 (16) | 0.0372 (15) | 0.0349 (14) | 0.0138 (12) | −0.0169 (12) | −0.0073 (11) |
C3 | 0.0189 (12) | 0.0290 (13) | 0.0347 (13) | 0.0007 (10) | −0.0075 (10) | −0.0076 (10) |
C4 | 0.0187 (12) | 0.0285 (12) | 0.0299 (12) | −0.0025 (9) | −0.0001 (9) | −0.0077 (10) |
C5 | 0.0231 (12) | 0.0211 (11) | 0.0312 (13) | −0.0049 (9) | 0.0028 (10) | −0.0024 (9) |
C6 | 0.0335 (14) | 0.0237 (12) | 0.0248 (12) | −0.0053 (10) | 0.0066 (10) | 0.0004 (9) |
C7 | 0.0294 (13) | 0.0315 (13) | 0.0286 (13) | −0.0070 (11) | 0.0104 (10) | −0.0078 (10) |
C8 | 0.0160 (12) | 0.0302 (13) | 0.0419 (14) | 0.0009 (10) | 0.0005 (10) | −0.0105 (11) |
C9 | 0.0606 (19) | 0.0311 (14) | 0.0240 (13) | 0.0053 (13) | −0.0017 (12) | 0.0013 (10) |
C17 | 0.0305 (14) | 0.0346 (14) | 0.0345 (14) | 0.0046 (11) | −0.0039 (11) | −0.0122 (11) |
C18 | 0.0352 (14) | 0.0262 (13) | 0.0342 (13) | 0.0022 (11) | −0.0022 (11) | −0.0046 (10) |
S1' | 0.0369 (4) | 0.0518 (4) | 0.0331 (4) | 0.0153 (3) | −0.0103 (3) | −0.0025 (3) |
C2' | 0.0308 (14) | 0.0584 (18) | 0.0264 (13) | 0.0063 (13) | −0.0003 (11) | −0.0119 (12) |
C3' | 0.0239 (12) | 0.0364 (14) | 0.0237 (12) | −0.0042 (10) | 0.0007 (9) | 0.0017 (10) |
C4' | 0.0214 (12) | 0.0253 (12) | 0.0280 (12) | −0.0034 (9) | −0.0021 (9) | 0.0007 (9) |
C5' | 0.0233 (12) | 0.0221 (12) | 0.0300 (12) | −0.0026 (9) | −0.0063 (10) | −0.0003 (9) |
C6' | 0.0283 (13) | 0.0185 (11) | 0.0380 (14) | 0.0009 (10) | −0.0062 (10) | −0.0067 (10) |
C7' | 0.0283 (13) | 0.0186 (12) | 0.0444 (15) | −0.0006 (10) | −0.0104 (11) | 0.0032 (10) |
C8' | 0.0351 (14) | 0.0321 (13) | 0.0268 (13) | −0.0051 (11) | −0.0064 (11) | 0.0090 (10) |
C9' | 0.0329 (14) | 0.0407 (15) | 0.0409 (15) | 0.0109 (12) | −0.0090 (12) | −0.0196 (12) |
C17' | 0.0247 (13) | 0.0401 (15) | 0.0324 (13) | 0.0048 (11) | −0.0043 (10) | −0.0059 (11) |
C18' | 0.0307 (14) | 0.0369 (14) | 0.0301 (13) | 0.0027 (11) | −0.0065 (11) | −0.0070 (11) |
S1" | 0.0504 (5) | 0.0475 (4) | 0.0471 (4) | −0.0123 (4) | −0.0004 (3) | 0.0177 (3) |
C2" | 0.0316 (14) | 0.0368 (14) | 0.0356 (14) | −0.0011 (11) | −0.0114 (11) | −0.0014 (11) |
C3" | 0.0163 (11) | 0.0291 (13) | 0.0330 (13) | 0.0045 (9) | −0.0053 (9) | −0.0001 (10) |
C4" | 0.0180 (12) | 0.0282 (12) | 0.0281 (12) | 0.0053 (9) | −0.0016 (9) | 0.0026 (10) |
C5" | 0.0206 (12) | 0.0230 (12) | 0.0331 (13) | 0.0052 (9) | 0.0016 (10) | −0.0008 (9) |
C6" | 0.0263 (13) | 0.0263 (12) | 0.0284 (12) | 0.0088 (10) | 0.0007 (10) | −0.0052 (10) |
C7" | 0.0259 (13) | 0.0322 (13) | 0.0278 (13) | 0.0069 (10) | 0.0052 (10) | 0.0018 (10) |
C8" | 0.0171 (12) | 0.0281 (13) | 0.0393 (14) | 0.0031 (10) | 0.0011 (10) | 0.0038 (10) |
C9" | 0.0440 (16) | 0.0365 (14) | 0.0307 (14) | 0.0041 (12) | −0.0067 (12) | −0.0073 (11) |
C17" | 0.0347 (15) | 0.0411 (15) | 0.0343 (14) | 0.0014 (12) | −0.0040 (11) | 0.0084 (11) |
C18" | 0.0302 (14) | 0.0256 (13) | 0.0446 (15) | 0.0015 (11) | −0.0058 (11) | 0.0020 (11) |
S1* | 0.0474 (5) | 0.0599 (5) | 0.0411 (4) | −0.0192 (4) | 0.0166 (3) | −0.0071 (3) |
C2* | 0.0323 (14) | 0.0392 (15) | 0.0364 (14) | −0.0045 (11) | −0.0027 (11) | −0.0145 (11) |
C3* | 0.0273 (13) | 0.0217 (12) | 0.0351 (13) | 0.0017 (10) | −0.0007 (10) | −0.0097 (10) |
C4* | 0.0272 (13) | 0.0218 (12) | 0.0268 (12) | 0.0043 (10) | 0.0017 (10) | −0.0043 (9) |
C5* | 0.0195 (12) | 0.0208 (11) | 0.0342 (13) | 0.0025 (9) | −0.0009 (10) | −0.0014 (9) |
C6* | 0.0232 (12) | 0.0273 (12) | 0.0280 (12) | 0.0058 (10) | −0.0056 (10) | 0.0005 (9) |
C7* | 0.0287 (13) | 0.0283 (13) | 0.0292 (13) | 0.0056 (10) | 0.0035 (10) | 0.0034 (10) |
C8* | 0.0235 (12) | 0.0200 (12) | 0.0394 (14) | −0.0005 (9) | 0.0037 (10) | −0.0012 (10) |
C9* | 0.0295 (14) | 0.0444 (15) | 0.0266 (13) | −0.0027 (11) | −0.0066 (10) | −0.0027 (11) |
C17* | 0.0369 (15) | 0.0396 (15) | 0.0302 (13) | −0.0024 (12) | 0.0040 (11) | −0.0062 (11) |
C18* | 0.0241 (13) | 0.0311 (13) | 0.0387 (14) | −0.0004 (10) | 0.0012 (11) | −0.0039 (11) |
S1—C18 | 1.814 (3) | S1"—C18" | 1.807 (3) |
S1—C17 | 1.824 (3) | S1"—C17" | 1.826 (3) |
C2—C3 | 1.511 (3) | C2"—C3" | 1.512 (3) |
C2—C9i | 1.589 (4) | C2"—C9"iii | 1.590 (4) |
C2—H2A | 0.9900 | C2"—H2"1 | 0.9900 |
C2—H2B | 0.9900 | C2"—H2"2 | 0.9900 |
C3—C8 | 1.387 (3) | C3"—C8" | 1.387 (3) |
C3—C4 | 1.402 (3) | C3"—C4" | 1.402 (3) |
C4—C5 | 1.386 (3) | C4"—C5" | 1.383 (3) |
C4—C17 | 1.507 (3) | C4"—C17" | 1.506 (3) |
C5—C6 | 1.402 (3) | C5"—C6" | 1.400 (3) |
C5—C18 | 1.504 (3) | C5"—C18" | 1.504 (3) |
C6—C7 | 1.390 (3) | C6"—C7" | 1.388 (3) |
C6—C9 | 1.508 (4) | C6"—C9" | 1.515 (3) |
C7—C8 | 1.384 (4) | C7"—C8" | 1.385 (3) |
C7—H7 | 0.9500 | C7"—H7" | 0.9500 |
C8—H8 | 0.9500 | C8"—H8" | 0.9500 |
C9—H9A | 0.9900 | C9"—H9"1 | 0.9900 |
C9—H9B | 0.9900 | C9"—H9"2 | 0.9900 |
C17—H17A | 0.9900 | C17"—H17E | 0.9900 |
C17—H17B | 0.9900 | C17"—H17F | 0.9900 |
C18—H18A | 0.9900 | C18"—H18E | 0.9900 |
C18—H18B | 0.9900 | C18"—H18F | 0.9900 |
S1'—C17' | 1.813 (2) | S1*—C18* | 1.811 (3) |
S1'—C18' | 1.819 (3) | S1*—C17* | 1.818 (3) |
C2'—C3' | 1.516 (3) | C2*—C3* | 1.514 (3) |
C2'—C9'ii | 1.585 (4) | C2*—C9*iv | 1.589 (4) |
C2'—H2'1 | 0.9900 | C2*—H2*1 | 0.9900 |
C2'—H2'2 | 0.9900 | C2*—H2*2 | 0.9900 |
C3'—C8' | 1.386 (3) | C3*—C8* | 1.387 (3) |
C3'—C4' | 1.400 (3) | C3*—C4* | 1.402 (3) |
C4'—C5' | 1.381 (3) | C4*—C5* | 1.384 (3) |
C4'—C17' | 1.502 (3) | C4*—C17* | 1.503 (3) |
C5'—C6' | 1.402 (3) | C5*—C6* | 1.403 (3) |
C5'—C18' | 1.507 (3) | C5*—C18* | 1.502 (3) |
C6'—C7' | 1.390 (3) | C6*—C7* | 1.388 (3) |
C6'—C9' | 1.507 (4) | C6*—C9* | 1.511 (3) |
C7'—C8' | 1.387 (4) | C7*—C8* | 1.386 (3) |
C7'—H7' | 0.9500 | C7*—H7* | 0.9500 |
C8'—H8' | 0.9500 | C8*—H8* | 0.9500 |
C9'—H9'1 | 0.9900 | C9*—H9*1 | 0.9900 |
C9'—H9'2 | 0.9900 | C9*—H9*2 | 0.9900 |
C17'—H17C | 0.9900 | C17*—H17G | 0.9900 |
C17'—H17D | 0.9900 | C17*—H17H | 0.9900 |
C18'—H18C | 0.9900 | C18*—H18G | 0.9900 |
C18'—H18D | 0.9900 | C18*—H18H | 0.9900 |
C18—S1—C17 | 95.62 (11) | C18"—S1"—C17" | 95.74 (12) |
C3—C2—C9i | 112.5 (2) | C3"—C2"—C9"iii | 112.9 (2) |
C3—C2—H2A | 109.1 | C3"—C2"—H2"1 | 109.0 |
C9i—C2—H2A | 109.1 | C9"iii—C2"—H2"1 | 109.0 |
C3—C2—H2B | 109.1 | C3"—C2"—H2"2 | 109.0 |
C9i—C2—H2B | 109.1 | C9"iii—C2"—H2"2 | 109.0 |
H2A—C2—H2B | 107.8 | H2"1—C2"—H2"2 | 107.8 |
C8—C3—C4 | 116.5 (2) | C8"—C3"—C4" | 116.6 (2) |
C8—C3—C2 | 120.8 (2) | C8"—C3"—C2" | 120.8 (2) |
C4—C3—C2 | 121.5 (2) | C4"—C3"—C2" | 121.5 (2) |
C5—C4—C3 | 120.7 (2) | C5"—C4"—C3" | 120.6 (2) |
C5—C4—C17 | 115.6 (2) | C5"—C4"—C17" | 115.6 (2) |
C3—C4—C17 | 123.3 (2) | C3"—C4"—C17" | 123.5 (2) |
C4—C5—C6 | 120.8 (2) | C4"—C5"—C6" | 120.9 (2) |
C4—C5—C18 | 115.9 (2) | C4"—C5"—C18" | 116.1 (2) |
C6—C5—C18 | 122.9 (2) | C6"—C5"—C18" | 122.7 (2) |
C7—C6—C5 | 116.5 (2) | C7"—C6"—C5" | 116.6 (2) |
C7—C6—C9 | 121.2 (2) | C7"—C6"—C9" | 121.2 (2) |
C5—C6—C9 | 121.0 (2) | C5"—C6"—C9" | 120.9 (2) |
C8—C7—C6 | 121.1 (2) | C8"—C7"—C6" | 120.9 (2) |
C8—C7—H7 | 119.5 | C8"—C7"—H7" | 119.5 |
C6—C7—H7 | 119.5 | C6"—C7"—H7" | 119.5 |
C7—C8—C3 | 121.2 (2) | C7"—C8"—C3" | 121.1 (2) |
C7—C8—H8 | 119.4 | C7"—C8"—H8" | 119.5 |
C3—C8—H8 | 119.4 | C3"—C8"—H8" | 119.5 |
C6—C9—C2i | 112.6 (2) | C6"—C9"—C2"iii | 112.0 (2) |
C6—C9—H9A | 109.1 | C6"—C9"—H9"1 | 109.2 |
C2i—C9—H9A | 109.1 | C2"iii—C9"—H9"1 | 109.2 |
C6—C9—H9B | 109.1 | C6"—C9"—H9"2 | 109.2 |
C2i—C9—H9B | 109.1 | C2"iii—C9"—H9"2 | 109.2 |
H9A—C9—H9B | 107.8 | H9"1—C9"—H9"2 | 107.9 |
C4—C17—S1 | 106.26 (17) | C4"—C17"—S1" | 106.08 (18) |
C4—C17—H17A | 110.5 | C4"—C17"—H17E | 110.5 |
S1—C17—H17A | 110.5 | S1"—C17"—H17E | 110.5 |
C4—C17—H17B | 110.5 | C4"—C17"—H17F | 110.5 |
S1—C17—H17B | 110.5 | S1"—C17"—H17F | 110.5 |
H17A—C17—H17B | 108.7 | H17E—C17"—H17F | 108.7 |
C5—C18—S1 | 106.57 (17) | C5"—C18"—S1" | 106.48 (17) |
C5—C18—H18A | 110.4 | C5"—C18"—H18E | 110.4 |
S1—C18—H18A | 110.4 | S1"—C18"—H18E | 110.4 |
C5—C18—H18B | 110.4 | C5"—C18"—H18F | 110.4 |
S1—C18—H18B | 110.4 | S1"—C18"—H18F | 110.4 |
H18A—C18—H18B | 108.6 | H18E—C18"—H18F | 108.6 |
C17'—S1'—C18' | 95.44 (11) | C18*—S1*—C17* | 95.87 (12) |
C3'—C2'—C9'ii | 111.9 (2) | C3*—C2*—C9*iv | 111.92 (19) |
C3'—C2'—H2'1 | 109.2 | C3*—C2*—H2*1 | 109.2 |
C9'ii—C2'—H2'1 | 109.2 | C9*iv—C2*—H2*1 | 109.2 |
C3'—C2'—H2'2 | 109.2 | C3*—C2*—H2*2 | 109.2 |
C9'ii—C2'—H2'2 | 109.2 | C9*iv—C2*—H2*2 | 109.2 |
H2'1—C2'—H2'2 | 107.9 | H2*1—C2*—H2*2 | 107.9 |
C8'—C3'—C4' | 116.6 (2) | C8*—C3*—C4* | 116.7 (2) |
C8'—C3'—C2' | 121.3 (2) | C8*—C3*—C2* | 120.5 (2) |
C4'—C3'—C2' | 120.7 (2) | C4*—C3*—C2* | 121.6 (2) |
C5'—C4'—C3' | 120.8 (2) | C5*—C4*—C3* | 120.4 (2) |
C5'—C4'—C17' | 115.7 (2) | C5*—C4*—C17* | 115.7 (2) |
C3'—C4'—C17' | 123.1 (2) | C3*—C4*—C17* | 123.5 (2) |
C4'—C5'—C6' | 120.8 (2) | C4*—C5*—C6* | 121.0 (2) |
C4'—C5'—C18' | 115.7 (2) | C4*—C5*—C18* | 116.0 (2) |
C6'—C5'—C18' | 123.1 (2) | C6*—C5*—C18* | 122.6 (2) |
C7'—C6'—C5' | 116.5 (2) | C7*—C6*—C5* | 116.4 (2) |
C7'—C6'—C9' | 121.4 (2) | C7*—C6*—C9* | 121.1 (2) |
C5'—C6'—C9' | 121.0 (2) | C5*—C6*—C9* | 121.4 (2) |
C8'—C7'—C6' | 121.0 (2) | C8*—C7*—C6* | 120.9 (2) |
C8'—C7'—H7' | 119.5 | C8*—C7*—H7* | 119.5 |
C6'—C7'—H7' | 119.5 | C6*—C7*—H7* | 119.5 |
C3'—C8'—C7' | 121.0 (2) | C7*—C8*—C3* | 121.1 (2) |
C3'—C8'—H8' | 119.5 | C7*—C8*—H8* | 119.4 |
C7'—C8'—H8' | 119.5 | C3*—C8*—H8* | 119.4 |
C6'—C9'—C2'ii | 113.3 (2) | C6*—C9*—C2*iv | 113.00 (19) |
C6'—C9'—H9'1 | 108.9 | C6*—C9*—H9*1 | 109.0 |
C2'ii—C9'—H9'1 | 108.9 | C2*iv—C9*—H9*1 | 109.0 |
C6'—C9'—H9'2 | 108.9 | C6*—C9*—H9*2 | 109.0 |
C2'ii—C9'—H9'2 | 108.9 | C2*iv—C9*—H9*2 | 109.0 |
H9'1—C9'—H9'2 | 107.7 | H9*1—C9*—H9*2 | 107.8 |
C4'—C17'—S1' | 106.72 (17) | C4*—C17*—S1* | 106.13 (17) |
C4'—C17'—H17C | 110.4 | C4*—C17*—H17G | 110.5 |
S1'—C17'—H17C | 110.4 | S1*—C17*—H17G | 110.5 |
C4'—C17'—H17D | 110.4 | C4*—C17*—H17H | 110.5 |
S1'—C17'—H17D | 110.4 | S1*—C17*—H17H | 110.5 |
H17C—C17'—H17D | 108.6 | H17G—C17*—H17H | 108.7 |
C5'—C18'—S1' | 106.36 (17) | C5*—C18*—S1* | 106.25 (17) |
C5'—C18'—H18C | 110.5 | C5*—C18*—H18G | 110.5 |
S1'—C18'—H18C | 110.5 | S1*—C18*—H18G | 110.5 |
C5'—C18'—H18D | 110.5 | C5*—C18*—H18H | 110.5 |
S1'—C18'—H18D | 110.5 | S1*—C18*—H18H | 110.5 |
H18C—C18'—H18D | 108.6 | H18G—C18*—H18H | 108.7 |
C9i—C2—C3—C8 | −95.1 (3) | C9"iii—C2"—C3"—C8" | 95.6 (3) |
C9i—C2—C3—C4 | 72.1 (3) | C9"iii—C2"—C3"—C4" | −72.2 (3) |
C8—C3—C4—C5 | 14.8 (3) | C8"—C3"—C4"—C5" | −15.2 (3) |
C2—C3—C4—C5 | −152.9 (2) | C2"—C3"—C4"—C5" | 153.1 (2) |
C8—C3—C4—C17 | −171.4 (2) | C8"—C3"—C4"—C17" | 171.6 (2) |
C2—C3—C4—C17 | 20.8 (3) | C2"—C3"—C4"—C17" | −20.1 (3) |
C3—C4—C5—C6 | −0.7 (3) | C3"—C4"—C5"—C6" | 1.0 (3) |
C17—C4—C5—C6 | −174.9 (2) | C17"—C4"—C5"—C6" | 174.7 (2) |
C3—C4—C5—C18 | 172.1 (2) | C3"—C4"—C5"—C18" | −172.2 (2) |
C17—C4—C5—C18 | −2.1 (3) | C17"—C4"—C5"—C18" | 1.5 (3) |
C4—C5—C6—C7 | −13.9 (3) | C4"—C5"—C6"—C7" | 14.0 (3) |
C18—C5—C6—C7 | 173.8 (2) | C18"—C5"—C6"—C7" | −173.2 (2) |
C4—C5—C6—C9 | 153.3 (2) | C4"—C5"—C6"—C9" | −153.3 (2) |
C18—C5—C6—C9 | −19.0 (3) | C18"—C5"—C6"—C9" | 19.5 (3) |
C5—C6—C7—C8 | 14.5 (3) | C5"—C6"—C7"—C8" | −14.9 (3) |
C9—C6—C7—C8 | −152.7 (2) | C9"—C6"—C7"—C8" | 152.3 (2) |
C6—C7—C8—C3 | −0.3 (4) | C6"—C7"—C8"—C3" | 0.7 (3) |
C4—C3—C8—C7 | −14.4 (3) | C4"—C3"—C8"—C7" | 14.4 (3) |
C2—C3—C8—C7 | 153.5 (2) | C2"—C3"—C8"—C7" | −154.0 (2) |
C7—C6—C9—C2i | 94.8 (3) | C7"—C6"—C9"—C2"iii | −95.2 (3) |
C5—C6—C9—C2i | −71.7 (3) | C5"—C6"—C9"—C2"iii | 71.5 (3) |
C5—C4—C17—S1 | 2.0 (3) | C5"—C4"—C17"—S1" | −0.3 (3) |
C3—C4—C17—S1 | −172.02 (19) | C3"—C4"—C17"—S1" | 173.21 (18) |
C18—S1—C17—C4 | −1.12 (19) | C18"—S1"—C17"—C4" | −0.73 (19) |
C4—C5—C18—S1 | 1.1 (3) | C4"—C5"—C18"—S1" | −1.9 (3) |
C6—C5—C18—S1 | 173.75 (19) | C6"—C5"—C18"—S1" | −175.04 (18) |
C17—S1—C18—C5 | 0.11 (19) | C17"—S1"—C18"—C5" | 1.44 (19) |
C9'ii—C2'—C3'—C8' | 94.3 (3) | C9*iv—C2*—C3*—C8* | −94.0 (3) |
C9'ii—C2'—C3'—C4' | −71.5 (3) | C9*iv—C2*—C3*—C4* | 72.9 (3) |
C8'—C3'—C4'—C5' | −14.4 (3) | C8*—C3*—C4*—C5* | 15.2 (3) |
C2'—C3'—C4'—C5' | 152.0 (2) | C2*—C3*—C4*—C5* | −152.1 (2) |
C8'—C3'—C4'—C17' | 172.8 (2) | C8*—C3*—C4*—C17* | −171.3 (2) |
C2'—C3'—C4'—C17' | −20.8 (4) | C2*—C3*—C4*—C17* | 21.4 (3) |
C3'—C4'—C5'—C6' | 0.0 (3) | C3*—C4*—C5*—C6* | −0.7 (3) |
C17'—C4'—C5'—C6' | 173.2 (2) | C17*—C4*—C5*—C6* | −174.8 (2) |
C3'—C4'—C5'—C18' | −173.7 (2) | C3*—C4*—C5*—C18* | 171.5 (2) |
C17'—C4'—C5'—C18' | −0.4 (3) | C17*—C4*—C5*—C18* | −2.5 (3) |
C4'—C5'—C6'—C7' | 14.1 (3) | C4*—C5*—C6*—C7* | −14.3 (3) |
C18'—C5'—C6'—C7' | −172.7 (2) | C18*—C5*—C6*—C7* | 174.0 (2) |
C4'—C5'—C6'—C9' | −154.4 (2) | C4*—C5*—C6*—C9* | 154.3 (2) |
C18'—C5'—C6'—C9' | 18.8 (4) | C18*—C5*—C6*—C9* | −17.5 (3) |
C5'—C6'—C7'—C8' | −13.8 (3) | C5*—C6*—C7*—C8* | 14.9 (3) |
C9'—C6'—C7'—C8' | 154.6 (2) | C9*—C6*—C7*—C8* | −153.7 (2) |
C4'—C3'—C8'—C7' | 14.8 (3) | C6*—C7*—C8*—C3* | −0.4 (4) |
C2'—C3'—C8'—C7' | −151.6 (2) | C4*—C3*—C8*—C7* | −14.7 (3) |
C6'—C7'—C8'—C3' | −0.6 (4) | C2*—C3*—C8*—C7* | 152.8 (2) |
C7'—C6'—C9'—C2'ii | −95.4 (3) | C7*—C6*—C9*—C2*iv | 94.8 (3) |
C5'—C6'—C9'—C2'ii | 72.5 (3) | C5*—C6*—C9*—C2*iv | −73.2 (3) |
C5'—C4'—C17'—S1' | −0.3 (3) | C5*—C4*—C17*—S1* | 1.4 (3) |
C3'—C4'—C17'—S1' | 172.78 (19) | C3*—C4*—C17*—S1* | −172.38 (19) |
C18'—S1'—C17'—C4' | 0.76 (19) | C18*—S1*—C17*—C4* | −0.04 (19) |
C4'—C5'—C18'—S1' | 1.0 (3) | C4*—C5*—C18*—S1* | 2.3 (3) |
C6'—C5'—C18'—S1' | −172.55 (19) | C6*—C5*—C18*—S1* | 174.38 (18) |
C17'—S1'—C18'—C5' | −0.97 (19) | C17*—S1*—C18*—C5* | −1.17 (18) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z; (iv) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2"—H2"2···S1′ | 0.99 | 2.95 | 3.723 (3) | 136 |
C9"—H9"2···S1′iii | 0.99 | 3.02 | 3.732 (3) | 130 |
C9*—H9*1···S1"v | 0.99 | 2.96 | 3.937 (3) | 168 |
C7—H7···S1*vi | 0.95 | 2.94 | 3.854 (3) | 162 |
C9′—H9′1···S1 | 0.99 | 3.07 | 3.907 (3) | 143 |
C8"—H8"···S1vii | 0.95 | 3.08 | 3.896 (3) | 145 |
C8*—H8*···S1′v | 0.95 | 3.10 | 3.879 (3) | 140 |
C17—H17B···S1*viii | 0.99 | 3.07 | 3.974 (3) | 153 |
C18"—H18F···Cg1ix | 1.08 | 2.74 | 3.63 | 140 |
C18—H18A···Cg3 | 1.08 | 2.78 | 3.66 | 111 |
C17′—H17C···Cg4ii | 1.08 | 2.61 | 3.45 | 135 |
C2*—H2*2···Cg2v | 1.08 | 2.98 | 4.04 | 166 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z; (v) x+1, y, z; (vi) x, y, z−1; (vii) −x+1, −y+1, −z; (viii) −x+1, −y, −z+1; (ix) x−1, y, z. |