Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034033/fl6185sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034033/fl6185Isup2.hkl |
CCDC reference: 293891
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C43H34ClPS | F(000) = 1360 |
Mr = 649.18 | Dx = 1.241 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9934 reflections |
a = 10.6924 (4) Å | θ = 2.2–29.9° |
b = 19.6175 (7) Å | µ = 0.25 mm−1 |
c = 16.5993 (6) Å | T = 173 K |
β = 93.773 (1)° | Oval, colorless |
V = 3474.3 (2) Å3 | 0.58 × 0.54 × 0.52 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 10126 independent reflections |
Radiation source: normal-focus sealed tube | 8519 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω scans | θmax = 30.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −15→15 |
Tmin = 0.80, Tmax = 0.88 | k = −27→27 |
51340 measured reflections | l = −23→23 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0712P)2 + 0.7845P] where P = (Fo2 + 2Fc2)/3 |
10126 reflections | (Δ/σ)max = 0.001 |
415 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −0.27 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 | ||
P | 0.03083 (3) | 0.145011 (15) | 0.281061 (17) | 0.02178 (7) | |
S | −0.06734 (3) | 0.228547 (16) | 0.28813 (2) | 0.03101 (8) | |
Cl | 0.59536 (4) | 0.34642 (2) | 0.18534 (3) | 0.05285 (11) | |
C1 | 0.31416 (10) | 0.13085 (6) | 0.13347 (7) | 0.0221 (2) | |
C2 | 0.21121 (10) | 0.16186 (6) | 0.16418 (6) | 0.0216 (2) | |
C3 | 0.12493 (11) | 0.19784 (6) | 0.11132 (7) | 0.0277 (2) | |
H3 | 0.0571 | 0.2215 | 0.1328 | 0.033* | |
C4 | 0.13774 (13) | 0.19903 (7) | 0.02994 (8) | 0.0315 (3) | |
H4 | 0.0789 | 0.2235 | −0.0043 | 0.038* | |
C5 | 0.23749 (12) | 0.16431 (6) | −0.00379 (7) | 0.0285 (2) | |
C6 | 0.24908 (16) | 0.16213 (7) | −0.08844 (8) | 0.0389 (3) | |
H6 | 0.1893 | 0.1852 | −0.1235 | 0.047* | |
C7 | 0.34467 (18) | 0.12749 (8) | −0.11997 (8) | 0.0449 (4) | |
H7 | 0.3505 | 0.1258 | −0.1768 | 0.054* | |
C8 | 0.43450 (16) | 0.09433 (8) | −0.06889 (9) | 0.0437 (4) | |
H8 | 0.5012 | 0.0705 | −0.0915 | 0.052* | |
C9 | 0.42780 (13) | 0.09567 (7) | 0.01363 (8) | 0.0350 (3) | |
H9 | 0.4903 | 0.0735 | 0.0475 | 0.042* | |
C10 | 0.32755 (11) | 0.13014 (6) | 0.04824 (7) | 0.0259 (2) | |
C11 | 0.41843 (10) | 0.10268 (6) | 0.18818 (7) | 0.0248 (2) | |
C12 | 0.51940 (11) | 0.14439 (7) | 0.21185 (7) | 0.0282 (2) | |
C13 | 0.61929 (12) | 0.11758 (8) | 0.26344 (9) | 0.0382 (3) | |
H13 | 0.6893 | 0.1457 | 0.2786 | 0.046* | |
C14 | 0.61610 (13) | 0.05254 (9) | 0.29123 (9) | 0.0414 (3) | |
H14 | 0.6840 | 0.0358 | 0.3255 | 0.050* | |
C15 | 0.51340 (13) | 0.00932 (7) | 0.27004 (8) | 0.0349 (3) | |
C16 | 0.50693 (16) | −0.05794 (8) | 0.30028 (10) | 0.0444 (3) | |
H16 | 0.5730 | −0.0747 | 0.3360 | 0.053* | |
C17 | 0.40801 (18) | −0.09891 (8) | 0.27913 (11) | 0.0496 (4) | |
H17 | 0.4044 | −0.1436 | 0.3009 | 0.060* | |
C18 | 0.31040 (17) | −0.07532 (8) | 0.22475 (11) | 0.0452 (3) | |
H18 | 0.2419 | −0.1044 | 0.2095 | 0.054* | |
C19 | 0.31407 (13) | −0.01037 (7) | 0.19376 (9) | 0.0342 (3) | |
H19 | 0.2485 | 0.0048 | 0.1566 | 0.041* | |
C20 | 0.41454 (11) | 0.03414 (6) | 0.21661 (7) | 0.0279 (2) | |
C21 | 0.19533 (10) | 0.16081 (6) | 0.25435 (6) | 0.0213 (2) | |
H21 | 0.2471 | 0.1221 | 0.2772 | 0.026* | |
C22 | 0.24903 (11) | 0.22677 (6) | 0.29475 (7) | 0.0267 (2) | |
H22A | 0.3263 | 0.2396 | 0.2687 | 0.032* | |
H22B | 0.1875 | 0.2640 | 0.2846 | 0.032* | |
C23 | 0.27919 (12) | 0.22092 (7) | 0.38457 (7) | 0.0288 (2) | |
C24 | 0.21339 (14) | 0.25906 (8) | 0.43862 (9) | 0.0379 (3) | |
H24 | 0.1503 | 0.2901 | 0.4191 | 0.045* | |
C25 | 0.24054 (17) | 0.25144 (9) | 0.52159 (9) | 0.0489 (4) | |
H25 | 0.1953 | 0.2774 | 0.5582 | 0.059* | |
C26 | 0.33163 (17) | 0.20701 (10) | 0.55099 (9) | 0.0488 (4) | |
H26 | 0.3488 | 0.2021 | 0.6076 | 0.059* | |
C27 | 0.39831 (15) | 0.16945 (9) | 0.49781 (9) | 0.0432 (3) | |
H27 | 0.4618 | 0.1388 | 0.5178 | 0.052* | |
C28 | 0.37247 (12) | 0.17654 (8) | 0.41500 (8) | 0.0345 (3) | |
H28 | 0.4190 | 0.1508 | 0.3788 | 0.041* | |
C29 | −0.03610 (11) | 0.08525 (6) | 0.20703 (7) | 0.0268 (2) | |
C30 | −0.12210 (14) | 0.10916 (8) | 0.14692 (9) | 0.0379 (3) | |
H30 | −0.1509 | 0.1549 | 0.1485 | 0.046* | |
C31 | −0.16586 (17) | 0.06649 (9) | 0.08476 (10) | 0.0499 (4) | |
H31 | −0.2244 | 0.0831 | 0.0438 | 0.060* | |
C32 | −0.12443 (19) | −0.00020 (9) | 0.08224 (10) | 0.0541 (4) | |
H32 | −0.1527 | −0.0290 | 0.0388 | 0.065* | |
C33 | −0.04215 (18) | −0.02495 (8) | 0.14273 (11) | 0.0504 (4) | |
H33 | −0.0157 | −0.0711 | 0.1415 | 0.060* | |
C34 | 0.00238 (14) | 0.01738 (7) | 0.20560 (9) | 0.0361 (3) | |
H34 | 0.0587 | 0.0001 | 0.2473 | 0.043* | |
C35 | 0.05520 (11) | 0.09905 (7) | 0.37694 (7) | 0.0275 (2) | |
H35A | 0.1029 | 0.0570 | 0.3670 | 0.033* | |
H35B | 0.1084 | 0.1277 | 0.4145 | 0.033* | |
C36 | −0.06063 (12) | 0.07930 (7) | 0.41888 (7) | 0.0312 (3) | |
C37 | −0.12535 (17) | 0.12700 (10) | 0.46142 (10) | 0.0506 (4) | |
H37 | −0.1012 | 0.1736 | 0.4609 | 0.061* | |
C38 | −0.2260 (2) | 0.10655 (14) | 0.50509 (13) | 0.0703 (6) | |
H38 | −0.2704 | 0.1394 | 0.5341 | 0.084* | |
C39 | −0.26158 (18) | 0.03919 (14) | 0.50659 (12) | 0.0688 (6) | |
H39 | −0.3297 | 0.0256 | 0.5369 | 0.083* | |
C40 | −0.19865 (15) | −0.00829 (11) | 0.46429 (10) | 0.0536 (5) | |
H40 | −0.2234 | −0.0548 | 0.4650 | 0.064* | |
C41 | −0.09855 (14) | 0.01157 (8) | 0.42041 (9) | 0.0384 (3) | |
H41 | −0.0554 | −0.0216 | 0.3911 | 0.046* | |
C42 | 0.52167 (12) | 0.21598 (7) | 0.18572 (8) | 0.0308 (3) | |
H42 | 0.4607 | 0.2300 | 0.1449 | 0.037* | |
C43 | 0.60235 (14) | 0.26213 (8) | 0.21497 (9) | 0.0381 (3) | |
H43 | 0.6667 | 0.2484 | 0.2538 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P | 0.01942 (13) | 0.02314 (14) | 0.02288 (14) | 0.00055 (10) | 0.00215 (10) | 0.00049 (10) |
S | 0.02517 (15) | 0.02865 (15) | 0.03962 (17) | 0.00602 (11) | 0.00539 (12) | −0.00097 (12) |
Cl | 0.0558 (2) | 0.03640 (19) | 0.0668 (3) | −0.00795 (16) | 0.0076 (2) | −0.00863 (17) |
C1 | 0.0220 (5) | 0.0234 (5) | 0.0209 (5) | −0.0005 (4) | 0.0018 (4) | −0.0004 (4) |
C2 | 0.0214 (5) | 0.0232 (5) | 0.0202 (5) | −0.0013 (4) | 0.0012 (4) | −0.0001 (4) |
C3 | 0.0256 (5) | 0.0302 (6) | 0.0270 (5) | 0.0046 (4) | 0.0008 (4) | 0.0032 (4) |
C4 | 0.0341 (6) | 0.0332 (6) | 0.0266 (6) | 0.0027 (5) | −0.0017 (5) | 0.0065 (5) |
C5 | 0.0366 (6) | 0.0273 (5) | 0.0218 (5) | −0.0052 (5) | 0.0028 (4) | 0.0023 (4) |
C6 | 0.0567 (9) | 0.0379 (7) | 0.0224 (6) | −0.0065 (6) | 0.0050 (6) | 0.0058 (5) |
C7 | 0.0704 (11) | 0.0418 (8) | 0.0244 (6) | −0.0086 (7) | 0.0168 (6) | 0.0006 (5) |
C8 | 0.0556 (9) | 0.0424 (8) | 0.0358 (7) | −0.0012 (7) | 0.0239 (7) | −0.0051 (6) |
C9 | 0.0375 (7) | 0.0373 (7) | 0.0315 (6) | 0.0020 (5) | 0.0125 (5) | −0.0017 (5) |
C10 | 0.0299 (6) | 0.0257 (5) | 0.0226 (5) | −0.0036 (4) | 0.0057 (4) | −0.0016 (4) |
C11 | 0.0202 (5) | 0.0319 (6) | 0.0228 (5) | 0.0041 (4) | 0.0035 (4) | −0.0001 (4) |
C12 | 0.0202 (5) | 0.0382 (6) | 0.0265 (5) | 0.0006 (4) | 0.0033 (4) | 0.0016 (5) |
C13 | 0.0226 (6) | 0.0530 (8) | 0.0383 (7) | 0.0011 (5) | −0.0029 (5) | 0.0054 (6) |
C14 | 0.0301 (6) | 0.0548 (9) | 0.0384 (7) | 0.0105 (6) | −0.0049 (5) | 0.0090 (6) |
C15 | 0.0348 (7) | 0.0388 (7) | 0.0315 (6) | 0.0120 (5) | 0.0049 (5) | 0.0047 (5) |
C16 | 0.0521 (9) | 0.0402 (8) | 0.0410 (8) | 0.0169 (7) | 0.0029 (6) | 0.0092 (6) |
C17 | 0.0662 (11) | 0.0311 (7) | 0.0522 (9) | 0.0116 (7) | 0.0090 (8) | 0.0078 (6) |
C18 | 0.0514 (9) | 0.0284 (7) | 0.0560 (9) | 0.0012 (6) | 0.0064 (7) | −0.0001 (6) |
C19 | 0.0354 (7) | 0.0289 (6) | 0.0386 (7) | 0.0039 (5) | 0.0043 (5) | −0.0011 (5) |
C20 | 0.0273 (5) | 0.0302 (6) | 0.0268 (5) | 0.0072 (4) | 0.0062 (4) | 0.0000 (4) |
C21 | 0.0194 (5) | 0.0241 (5) | 0.0205 (5) | 0.0007 (4) | 0.0017 (4) | −0.0016 (4) |
C22 | 0.0268 (5) | 0.0284 (5) | 0.0250 (5) | −0.0046 (4) | 0.0031 (4) | −0.0038 (4) |
C23 | 0.0277 (6) | 0.0336 (6) | 0.0253 (5) | −0.0111 (5) | 0.0034 (4) | −0.0059 (4) |
C24 | 0.0404 (7) | 0.0408 (7) | 0.0333 (7) | −0.0095 (6) | 0.0087 (5) | −0.0118 (5) |
C25 | 0.0576 (10) | 0.0585 (10) | 0.0324 (7) | −0.0209 (8) | 0.0160 (7) | −0.0186 (7) |
C26 | 0.0541 (9) | 0.0670 (11) | 0.0250 (6) | −0.0293 (8) | −0.0006 (6) | −0.0026 (6) |
C27 | 0.0371 (7) | 0.0574 (9) | 0.0340 (7) | −0.0168 (7) | −0.0072 (6) | 0.0048 (6) |
C28 | 0.0285 (6) | 0.0452 (7) | 0.0298 (6) | −0.0087 (5) | 0.0008 (5) | −0.0028 (5) |
C29 | 0.0250 (5) | 0.0284 (6) | 0.0270 (5) | −0.0054 (4) | 0.0012 (4) | −0.0005 (4) |
C30 | 0.0382 (7) | 0.0362 (7) | 0.0378 (7) | −0.0046 (6) | −0.0089 (6) | 0.0017 (5) |
C31 | 0.0561 (10) | 0.0507 (9) | 0.0404 (8) | −0.0161 (8) | −0.0168 (7) | 0.0015 (7) |
C32 | 0.0703 (12) | 0.0477 (9) | 0.0432 (8) | −0.0248 (8) | −0.0058 (8) | −0.0102 (7) |
C33 | 0.0627 (11) | 0.0327 (7) | 0.0551 (9) | −0.0087 (7) | −0.0016 (8) | −0.0106 (7) |
C34 | 0.0383 (7) | 0.0293 (6) | 0.0404 (7) | −0.0038 (5) | −0.0004 (6) | −0.0023 (5) |
C35 | 0.0240 (5) | 0.0330 (6) | 0.0254 (5) | −0.0021 (4) | 0.0008 (4) | 0.0047 (4) |
C36 | 0.0268 (6) | 0.0421 (7) | 0.0246 (5) | −0.0031 (5) | 0.0006 (4) | 0.0072 (5) |
C37 | 0.0522 (9) | 0.0579 (10) | 0.0437 (8) | 0.0022 (8) | 0.0194 (7) | 0.0037 (7) |
C38 | 0.0579 (11) | 0.0987 (17) | 0.0580 (11) | 0.0127 (11) | 0.0322 (10) | 0.0114 (11) |
C39 | 0.0387 (9) | 0.1160 (19) | 0.0529 (10) | −0.0084 (10) | 0.0121 (8) | 0.0373 (12) |
C40 | 0.0377 (8) | 0.0748 (12) | 0.0461 (9) | −0.0235 (8) | −0.0124 (7) | 0.0318 (8) |
C41 | 0.0338 (7) | 0.0465 (8) | 0.0335 (6) | −0.0106 (6) | −0.0077 (5) | 0.0138 (6) |
C42 | 0.0235 (5) | 0.0398 (7) | 0.0292 (6) | −0.0023 (5) | 0.0035 (4) | 0.0016 (5) |
C43 | 0.0369 (7) | 0.0385 (7) | 0.0385 (7) | 0.0001 (6) | −0.0005 (6) | −0.0076 (6) |
P—C29 | 1.8113 (12) | C22—H22A | 0.9900 |
P—C35 | 1.8328 (12) | C22—H22B | 0.9900 |
P—C21 | 1.8678 (11) | C23—C28 | 1.393 (2) |
P—S | 1.9538 (4) | C23—C24 | 1.3938 (18) |
C1—C2 | 1.3840 (15) | C24—C25 | 1.397 (2) |
C1—C10 | 1.4314 (15) | C24—H24 | 0.9500 |
C1—C11 | 1.4966 (15) | C25—C26 | 1.373 (3) |
C2—C3 | 1.4187 (16) | C25—H25 | 0.9500 |
C21—C2 | 1.5175 (15) | C26—C27 | 1.383 (3) |
C3—C4 | 1.3669 (17) | C26—H26 | 0.9500 |
C3—H3 | 0.9500 | C27—C28 | 1.3912 (19) |
C4—C5 | 1.4119 (19) | C27—H27 | 0.9500 |
C4—H4 | 0.9500 | C28—H28 | 0.9500 |
C5—C10 | 1.4190 (18) | C29—C30 | 1.3929 (18) |
C5—C6 | 1.4194 (17) | C29—C34 | 1.3944 (19) |
C6—C7 | 1.360 (2) | C30—C31 | 1.386 (2) |
C6—H6 | 0.9500 | C30—H30 | 0.9500 |
C7—C8 | 1.399 (3) | C31—C32 | 1.383 (3) |
C7—H7 | 0.9500 | C31—H31 | 0.9500 |
C8—C9 | 1.3766 (19) | C32—C33 | 1.379 (3) |
C8—H8 | 0.9500 | C32—H32 | 0.9500 |
C9—C10 | 1.4203 (17) | C33—C34 | 1.393 (2) |
C9—H9 | 0.9500 | C33—H33 | 0.9500 |
C11—C12 | 1.3906 (17) | C34—H34 | 0.9500 |
C11—C20 | 1.4265 (17) | C35—C36 | 1.5107 (17) |
C12—C13 | 1.4249 (18) | C35—H35A | 0.9900 |
C13—C14 | 1.358 (2) | C35—H35B | 0.9900 |
C13—H13 | 0.9500 | C36—C37 | 1.385 (2) |
C14—C15 | 1.413 (2) | C36—C41 | 1.390 (2) |
C14—H14 | 0.9500 | C37—C38 | 1.395 (2) |
C15—C16 | 1.415 (2) | C37—H37 | 0.9500 |
C15—C20 | 1.4203 (18) | C38—C39 | 1.376 (4) |
C16—C17 | 1.356 (3) | C38—H38 | 0.9500 |
C16—H16 | 0.9500 | C39—C40 | 1.369 (3) |
C17—C18 | 1.412 (3) | C39—H39 | 0.9500 |
C17—H17 | 0.9500 | C40—C41 | 1.389 (2) |
C18—C19 | 1.376 (2) | C40—H40 | 0.9500 |
C18—H18 | 0.9500 | C41—H41 | 0.9500 |
C19—C20 | 1.4165 (19) | C12—C42 | 1.4705 (19) |
C19—H19 | 0.9500 | C42—C43 | 1.3208 (19) |
C21—C22 | 1.5503 (16) | C42—H42 | 0.9500 |
C21—H21 | 1.0000 | C43—H43 | 0.9500 |
C22—C23 | 1.5090 (17) | C43—Cl | 1.7253 (16) |
C29—P—C35 | 107.34 (6) | C23—C22—C21 | 114.39 (10) |
C29—P—C21 | 106.41 (5) | C23—C22—H22A | 108.7 |
C35—P—C21 | 101.85 (5) | C21—C22—H22A | 108.7 |
C29—P—S | 113.19 (4) | C23—C22—H22B | 108.7 |
C35—P—S | 114.00 (4) | C21—C22—H22B | 108.7 |
C21—P—S | 113.15 (4) | H22A—C22—H22B | 107.6 |
C2—C1—C10 | 120.14 (10) | C28—C23—C24 | 118.79 (13) |
C2—C1—C11 | 121.18 (10) | C28—C23—C22 | 120.47 (11) |
C10—C1—C11 | 118.49 (10) | C24—C23—C22 | 120.74 (13) |
C1—C2—C3 | 119.44 (10) | C23—C24—C25 | 119.76 (16) |
C1—C2—C21 | 120.04 (10) | C23—C24—H24 | 120.1 |
C3—C2—C21 | 120.42 (10) | C25—C24—H24 | 120.1 |
C4—C3—C2 | 121.09 (11) | C26—C25—C24 | 121.00 (15) |
C4—C3—H3 | 119.5 | C26—C25—H25 | 119.5 |
C2—C3—H3 | 119.5 | C24—C25—H25 | 119.5 |
C3—C4—C5 | 120.74 (11) | C25—C26—C27 | 119.67 (14) |
C3—C4—H4 | 119.6 | C25—C26—H26 | 120.2 |
C5—C4—H4 | 119.6 | C27—C26—H26 | 120.2 |
C4—C5—C10 | 119.12 (11) | C26—C27—C28 | 120.00 (16) |
C4—C5—C6 | 121.64 (12) | C26—C27—H27 | 120.0 |
C10—C5—C6 | 119.23 (12) | C28—C27—H27 | 120.0 |
C7—C6—C5 | 120.84 (14) | C27—C28—C23 | 120.77 (14) |
C7—C6—H6 | 119.6 | C27—C28—H28 | 119.6 |
C5—C6—H6 | 119.6 | C23—C28—H28 | 119.6 |
C6—C7—C8 | 120.16 (13) | C30—C29—C34 | 119.41 (12) |
C6—C7—H7 | 119.9 | C30—C29—P | 118.74 (10) |
C8—C7—H7 | 119.9 | C34—C29—P | 121.72 (10) |
C9—C8—C7 | 121.04 (14) | C31—C30—C29 | 120.30 (14) |
C9—C8—H8 | 119.5 | C31—C30—H30 | 119.8 |
C7—C8—H8 | 119.5 | C29—C30—H30 | 119.8 |
C8—C9—C10 | 120.11 (14) | C32—C31—C30 | 120.06 (15) |
C8—C9—H9 | 119.9 | C32—C31—H31 | 120.0 |
C10—C9—H9 | 119.9 | C30—C31—H31 | 120.0 |
C5—C10—C9 | 118.60 (11) | C33—C32—C31 | 120.09 (15) |
C5—C10—C1 | 119.27 (11) | C33—C32—H32 | 120.0 |
C9—C10—C1 | 122.12 (11) | C31—C32—H32 | 120.0 |
C12—C11—C20 | 120.01 (11) | C32—C33—C34 | 120.39 (16) |
C12—C11—C1 | 119.18 (11) | C32—C33—H33 | 119.8 |
C20—C11—C1 | 120.80 (10) | C34—C33—H33 | 119.8 |
C11—C12—C13 | 119.33 (12) | C33—C34—C29 | 119.69 (14) |
C11—C12—C42 | 120.41 (11) | C33—C34—H34 | 120.2 |
C13—C12—C42 | 120.23 (12) | C29—C34—H34 | 120.2 |
C14—C13—C12 | 121.09 (13) | C36—C35—P | 116.89 (8) |
C14—C13—H13 | 119.5 | C36—C35—H35A | 108.1 |
C12—C13—H13 | 119.5 | P—C35—H35A | 108.1 |
C13—C14—C15 | 121.03 (13) | C36—C35—H35B | 108.1 |
C13—C14—H14 | 119.5 | P—C35—H35B | 108.1 |
C15—C14—H14 | 119.5 | H35A—C35—H35B | 107.3 |
C14—C15—C16 | 121.75 (13) | C37—C36—C41 | 118.72 (14) |
C14—C15—C20 | 118.94 (13) | C37—C36—C35 | 120.93 (13) |
C16—C15—C20 | 119.30 (14) | C41—C36—C35 | 120.17 (13) |
C17—C16—C15 | 121.08 (14) | C36—C37—C38 | 119.94 (19) |
C17—C16—H16 | 119.5 | C36—C37—H37 | 120.0 |
C15—C16—H16 | 119.5 | C38—C37—H37 | 120.0 |
C16—C17—C18 | 120.15 (15) | C39—C38—C37 | 120.6 (2) |
C16—C17—H17 | 119.9 | C39—C38—H38 | 119.7 |
C18—C17—H17 | 119.9 | C37—C38—H38 | 119.7 |
C19—C18—C17 | 120.30 (16) | C40—C39—C38 | 119.89 (16) |
C19—C18—H18 | 119.9 | C40—C39—H39 | 120.1 |
C17—C18—H18 | 119.9 | C38—C39—H39 | 120.1 |
C18—C19—C20 | 120.70 (14) | C39—C40—C41 | 119.97 (18) |
C18—C19—H19 | 119.6 | C39—C40—H40 | 120.0 |
C20—C19—H19 | 119.6 | C41—C40—H40 | 120.0 |
C19—C20—C15 | 118.43 (12) | C40—C41—C36 | 120.88 (17) |
C19—C20—C11 | 122.04 (11) | C40—C41—H41 | 119.6 |
C15—C20—C11 | 119.53 (12) | C36—C41—H41 | 119.6 |
C2—C21—C22 | 110.66 (9) | C12—C42—C43 | 124.70 (13) |
C2—C21—P | 113.87 (7) | C43—C42—H42 | 117.6 |
C22—C21—P | 111.32 (8) | C12—C42—H42 | 117.6 |
C2—C21—H21 | 106.9 | C42—C43—Cl | 122.49 (12) |
C22—C21—H21 | 106.9 | C42—C43—H43 | 118.8 |
P—C21—H21 | 106.9 | Cl—C43—H43 | 118.8 |
C10—C1—C2—C3 | −5.34 (17) | C1—C2—C21—C22 | 94.86 (12) |
C11—C1—C2—C3 | 169.54 (11) | C3—C2—C21—C22 | −81.50 (13) |
C10—C1—C2—C21 | 178.26 (10) | C1—C2—C21—P | −138.86 (9) |
C11—C1—C2—C21 | −6.86 (16) | C3—C2—C21—P | 44.78 (13) |
C1—C2—C3—C4 | 3.88 (18) | C29—P—C21—C2 | 35.99 (9) |
C21—C2—C3—C4 | −179.74 (11) | C35—P—C21—C2 | 148.28 (8) |
C2—C3—C4—C5 | 0.0 (2) | S—P—C21—C2 | −88.92 (8) |
C3—C4—C5—C10 | −2.39 (19) | C29—P—C21—C22 | 161.93 (8) |
C3—C4—C5—C6 | 176.90 (13) | C35—P—C21—C22 | −85.78 (9) |
C4—C5—C6—C7 | −178.91 (14) | S—P—C21—C22 | 37.02 (9) |
C10—C5—C6—C7 | 0.4 (2) | C2—C21—C22—C23 | −159.72 (10) |
C5—C6—C7—C8 | −1.1 (2) | P—C21—C22—C23 | 72.59 (12) |
C6—C7—C8—C9 | 0.4 (2) | C21—C22—C23—C28 | 64.48 (15) |
C7—C8—C9—C10 | 1.0 (2) | C21—C22—C23—C24 | −114.70 (13) |
C4—C5—C10—C9 | −179.70 (12) | C28—C23—C24—C25 | −0.9 (2) |
C6—C5—C10—C9 | 0.99 (18) | C22—C23—C24—C25 | 178.24 (13) |
C4—C5—C10—C1 | 0.88 (17) | C23—C24—C25—C26 | 0.2 (2) |
C6—C5—C10—C1 | −178.43 (11) | C24—C25—C26—C27 | 0.4 (2) |
C8—C9—C10—C5 | −1.7 (2) | C25—C26—C27—C28 | −0.3 (2) |
C8—C9—C10—C1 | 177.72 (13) | C26—C27—C28—C23 | −0.4 (2) |
C2—C1—C10—C5 | 3.01 (17) | C24—C23—C28—C27 | 1.05 (19) |
C11—C1—C10—C5 | −172.01 (11) | C22—C23—C28—C27 | −178.14 (12) |
C2—C1—C10—C9 | −176.39 (12) | C35—P—C29—C30 | 145.98 (11) |
C11—C1—C10—C9 | 8.59 (17) | C21—P—C29—C30 | −105.58 (11) |
C2—C1—C11—C12 | −90.49 (14) | S—P—C29—C30 | 19.31 (12) |
C10—C1—C11—C12 | 84.48 (14) | C35—P—C29—C34 | −38.33 (12) |
C2—C1—C11—C20 | 88.92 (14) | C21—P—C29—C34 | 70.11 (12) |
C10—C1—C11—C20 | −96.12 (13) | S—P—C29—C34 | −165.00 (10) |
C20—C11—C12—C13 | 1.07 (17) | C34—C29—C30—C31 | −2.1 (2) |
C1—C11—C12—C13 | −179.52 (11) | P—C29—C30—C31 | 173.65 (13) |
C20—C11—C12—C42 | −177.34 (11) | C29—C30—C31—C32 | 0.1 (3) |
C1—C11—C12—C42 | 2.07 (17) | C30—C31—C32—C33 | 1.8 (3) |
C11—C12—C13—C14 | −1.5 (2) | C31—C32—C33—C34 | −1.7 (3) |
C42—C12—C13—C14 | 176.92 (13) | C32—C33—C34—C29 | −0.3 (3) |
C12—C13—C14—C15 | −0.1 (2) | C30—C29—C34—C33 | 2.2 (2) |
C13—C14—C15—C16 | −178.19 (14) | P—C29—C34—C33 | −173.43 (12) |
C13—C14—C15—C20 | 2.1 (2) | C29—P—C35—C36 | −70.27 (11) |
C14—C15—C16—C17 | −179.72 (15) | C21—P—C35—C36 | 178.15 (10) |
C20—C15—C16—C17 | −0.1 (2) | S—P—C35—C36 | 55.93 (11) |
C15—C16—C17—C18 | 1.4 (3) | P—C35—C36—C37 | −77.21 (16) |
C16—C17—C18—C19 | −0.9 (3) | P—C35—C36—C41 | 107.65 (13) |
C17—C18—C19—C20 | −0.9 (2) | C41—C36—C37—C38 | 0.4 (3) |
C18—C19—C20—C15 | 2.13 (19) | C35—C36—C37—C38 | −174.82 (16) |
C18—C19—C20—C11 | −177.34 (13) | C36—C37—C38—C39 | 0.2 (3) |
C14—C15—C20—C19 | 178.00 (12) | C37—C38—C39—C40 | −0.6 (3) |
C16—C15—C20—C19 | −1.68 (19) | C38—C39—C40—C41 | 0.4 (3) |
C14—C15—C20—C11 | −2.51 (18) | C39—C40—C41—C36 | 0.2 (2) |
C16—C15—C20—C11 | 177.81 (12) | C37—C36—C41—C40 | −0.6 (2) |
C12—C11—C20—C19 | −179.61 (11) | C35—C36—C41—C40 | 174.65 (12) |
C1—C11—C20—C19 | 0.99 (17) | C11—C12—C42—C43 | 168.68 (13) |
C12—C11—C20—C15 | 0.92 (17) | C13—C12—C42—C43 | −9.7 (2) |
C1—C11—C20—C15 | −178.47 (11) | C12—C42—C43—Cl | −176.72 (10) |