Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000433/qa0201sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000433/qa0201Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000433/qa0201IIsup3.hkl |
CCDC references: 142938; 142939
A solution of triphenylphosphine in benzene was slowly dropped to a suspension of pyridinedithiomonometaphosphoryl chloride or fluoride in benzene. After 1 h, the solid products were filtrated and recrystallized from benzene. For the studied crystals, a ΔF2-based absorption correction was carried out. The calculation was done with ABSCOR (Stoe & Cie, 1996), a modification of DIFABS (Walker & Stuart, 1983). In contrary of DIFABS, ABSCOR loads and provides F2 values instead of F ones.
For both compounds, data collection: IPDS2.87 (Stoe & Cie, 1997); cell refinement: IPDS2.87 (Stoe & Cie, 1997); data reduction: IPDS2.87 (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XSTEP-2.18 (Stoe & Cie, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C18H15P | Z = 8 |
Mr = 262.27 | F(000) = 1104 |
Triclinic, P1 | Dx = 1.216 Mg m−3 |
a = 11.0306 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.111 (3) Å | Cell parameters from 5000 reflections |
c = 17.554 (3) Å | θ = 2.5–25.0° |
α = 84.38 (2)° | µ = 0.18 mm−1 |
β = 80.36 (2)° | T = 180 K |
γ = 85.82 (2)° | Block, colorless |
V = 2866.0 (8) Å3 | 0.48 × 0.48 × 0.28 mm |
Stoe IPDS diffractometer | 9738 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 6818 reflections with I > 2σ(I) |
Planar graphite monochromator | Rint = 0.032 |
Detector resolution: 6.667 pixels mm-1 | θmax = 25.3°, θmin = 2.3° |
ϕ–oscill.,ϕ–incr.=1.4°,164 exposures scans | h = −13→13 |
Absorption correction: part of the refinement model (ΔF) see _publ_section_exptl_prep | k = −18→18 |
Tmin = 0.921, Tmax = 0.953 | l = −20→20 |
17345 measured 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0683P)2] where P = (Fo2 + 2Fc2)/3 |
9738 reflections | (Δ/σ)max = 0.004 |
685 parameters | Δρmax = 1.02 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C18H15P | γ = 85.82 (2)° |
Mr = 262.27 | V = 2866.0 (8) Å3 |
Triclinic, P1 | Z = 8 |
a = 11.0306 (19) Å | Mo Kα radiation |
b = 15.111 (3) Å | µ = 0.18 mm−1 |
c = 17.554 (3) Å | T = 180 K |
α = 84.38 (2)° | 0.48 × 0.48 × 0.28 mm |
β = 80.36 (2)° |
Stoe IPDS diffractometer | 9738 independent reflections |
Absorption correction: part of the refinement model (ΔF) see _publ_section_exptl_prep | 6818 reflections with I > 2σ(I) |
Tmin = 0.921, Tmax = 0.953 | Rint = 0.032 |
17345 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 0.92 | Δρmax = 1.02 e Å−3 |
9738 reflections | Δρmin = −0.23 e Å−3 |
685 parameters |
Experimental. see _publ_section_exptl_prep |
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 | ||
C1 | 0.00732 (17) | 0.27383 (12) | 0.53322 (12) | 0.0277 (4) | |
C2 | 0.0936 (2) | 0.22447 (13) | 0.57254 (13) | 0.0347 (5) | |
H2 | 0.1661 | 0.1987 | 0.5439 | 0.042* | |
C3 | 0.0748 (2) | 0.21288 (14) | 0.65211 (14) | 0.0417 (6) | |
H3 | 0.1341 | 0.1794 | 0.6782 | 0.050* | |
C4 | −0.0305 (2) | 0.24995 (14) | 0.69410 (14) | 0.0428 (6) | |
H4 | −0.0439 | 0.2413 | 0.7491 | 0.051* | |
C5 | −0.1161 (2) | 0.29947 (15) | 0.65643 (14) | 0.0401 (5) | |
H5 | −0.1881 | 0.3254 | 0.6855 | 0.048* | |
C6 | −0.09737 (18) | 0.31147 (14) | 0.57646 (13) | 0.0328 (5) | |
H6 | −0.1566 | 0.3458 | 0.5508 | 0.039* | |
C7 | −0.07266 (17) | 0.37660 (12) | 0.40449 (11) | 0.0263 (4) | |
C8 | −0.04735 (19) | 0.46494 (13) | 0.40897 (13) | 0.0339 (5) | |
H8 | 0.0286 | 0.4779 | 0.4229 | 0.041* | |
C9 | −0.1317 (2) | 0.53367 (13) | 0.39329 (14) | 0.0393 (5) | |
H9 | −0.1141 | 0.5934 | 0.3975 | 0.047* | |
C10 | −0.2414 (2) | 0.51590 (14) | 0.37150 (13) | 0.0377 (5) | |
H10 | −0.2990 | 0.5633 | 0.3605 | 0.045* | |
C11 | −0.26716 (19) | 0.42895 (14) | 0.36574 (13) | 0.0370 (5) | |
H11 | −0.3423 | 0.4167 | 0.3503 | 0.044* | |
C12 | −0.18401 (18) | 0.35977 (13) | 0.38235 (13) | 0.0322 (5) | |
H12 | −0.2028 | 0.3001 | 0.3787 | 0.039* | |
C13 | −0.01417 (18) | 0.19020 (12) | 0.39731 (12) | 0.0293 (5) | |
C14 | −0.0675 (2) | 0.12202 (13) | 0.44773 (13) | 0.0362 (5) | |
H14 | −0.0796 | 0.1268 | 0.5021 | 0.043* | |
C15 | −0.1035 (2) | 0.04691 (14) | 0.41957 (15) | 0.0453 (6) | |
H15 | −0.1385 | 0.0002 | 0.4548 | 0.054* | |
C16 | −0.0887 (2) | 0.03984 (15) | 0.34111 (16) | 0.0480 (6) | |
H16 | −0.1147 | −0.0111 | 0.3219 | 0.058* | |
C17 | −0.0360 (2) | 0.10690 (15) | 0.29048 (15) | 0.0443 (6) | |
H17 | −0.0253 | 0.1022 | 0.2362 | 0.053* | |
C18 | 0.0013 (2) | 0.18089 (14) | 0.31816 (13) | 0.0364 (5) | |
H18 | 0.0384 | 0.2264 | 0.2825 | 0.044* | |
C21 | −0.2074 (2) | 0.91075 (15) | 0.08825 (13) | 0.0371 (5) | |
C22 | −0.1657 (2) | 0.99603 (16) | 0.07155 (16) | 0.0498 (6) | |
H22 | −0.1118 | 1.0097 | 0.0243 | 0.060* | |
C23 | −0.2002 (3) | 1.06103 (19) | 0.1214 (2) | 0.0648 (8) | |
H23 | −0.1722 | 1.1194 | 0.1083 | 0.078* | |
C24 | −0.2751 (3) | 1.0411 (2) | 0.1900 (2) | 0.0700 (9) | |
H24 | −0.2982 | 1.0856 | 0.2252 | 0.084* | |
C25 | −0.3174 (3) | 0.9574 (2) | 0.20869 (17) | 0.0691 (9) | |
H25 | −0.3699 | 0.9442 | 0.2566 | 0.083* | |
C26 | −0.2836 (2) | 0.89173 (19) | 0.15767 (15) | 0.0537 (7) | |
H26 | −0.3132 | 0.8338 | 0.1707 | 0.064* | |
C27 | −0.2621 (2) | 0.85088 (13) | −0.05018 (13) | 0.0349 (5) | |
C28 | −0.3821 (2) | 0.88611 (16) | −0.03124 (14) | 0.0454 (6) | |
H28 | −0.4115 | 0.9009 | 0.0202 | 0.054* | |
C29 | −0.4589 (2) | 0.89985 (17) | −0.08586 (16) | 0.0530 (7) | |
H29 | −0.5407 | 0.9239 | −0.0720 | 0.064* | |
C30 | −0.4173 (2) | 0.87874 (16) | −0.16084 (15) | 0.0490 (6) | |
H30 | −0.4702 | 0.8888 | −0.1987 | 0.059* | |
C31 | −0.2998 (2) | 0.84328 (15) | −0.18057 (14) | 0.0468 (6) | |
H31 | −0.2716 | 0.8280 | −0.2320 | 0.056* | |
C32 | −0.2219 (2) | 0.82964 (14) | −0.12594 (13) | 0.0396 (5) | |
H32 | −0.1402 | 0.8055 | −0.1403 | 0.048* | |
C33 | −0.19759 (19) | 0.72502 (14) | 0.07042 (13) | 0.0356 (5) | |
C34 | −0.2857 (2) | 0.67289 (14) | 0.05271 (14) | 0.0407 (5) | |
H34 | −0.3292 | 0.6929 | 0.0113 | 0.049* | |
C35 | −0.3112 (3) | 0.59183 (15) | 0.09464 (16) | 0.0516 (7) | |
H35 | −0.3717 | 0.5568 | 0.0818 | 0.062* | |
C36 | −0.2492 (3) | 0.56233 (16) | 0.15459 (16) | 0.0537 (7) | |
H36 | −0.2669 | 0.5070 | 0.1835 | 0.064* | |
C37 | −0.1614 (3) | 0.6131 (2) | 0.17281 (16) | 0.0610 (8) | |
H37 | −0.1187 | 0.5929 | 0.2146 | 0.073* | |
C38 | −0.1350 (2) | 0.69300 (18) | 0.13069 (15) | 0.0538 (7) | |
H38 | −0.0729 | 0.7269 | 0.1431 | 0.065* | |
C41 | 0.29537 (19) | 0.74993 (13) | 0.07740 (12) | 0.0319 (5) | |
C42 | 0.3783 (2) | 0.78111 (15) | 0.11877 (15) | 0.0436 (6) | |
H42 | 0.4552 | 0.7492 | 0.1212 | 0.052* | |
C43 | 0.3501 (2) | 0.85822 (16) | 0.15653 (16) | 0.0512 (6) | |
H43 | 0.4073 | 0.8785 | 0.1849 | 0.061* | |
C44 | 0.2393 (2) | 0.90541 (15) | 0.15289 (14) | 0.0463 (6) | |
H44 | 0.2201 | 0.9585 | 0.1784 | 0.056* | |
C45 | 0.1566 (2) | 0.87541 (15) | 0.11227 (14) | 0.0446 (6) | |
H45 | 0.0799 | 0.9078 | 0.1102 | 0.053* | |
C46 | 0.1838 (2) | 0.79848 (14) | 0.07436 (13) | 0.0387 (5) | |
H46 | 0.1261 | 0.7787 | 0.0461 | 0.046* | |
C47 | 0.2316 (2) | 0.64744 (13) | −0.03721 (12) | 0.0334 (5) | |
C48 | 0.2676 (2) | 0.68455 (14) | −0.11264 (13) | 0.0415 (6) | |
H48 | 0.3463 | 0.7085 | −0.1269 | 0.050* | |
C49 | 0.1902 (3) | 0.68685 (16) | −0.16678 (15) | 0.0507 (7) | |
H49 | 0.2153 | 0.7134 | −0.2178 | 0.061* | |
C50 | 0.0771 (2) | 0.65119 (15) | −0.14779 (15) | 0.0466 (6) | |
H50 | 0.0249 | 0.6520 | −0.1858 | 0.056* | |
C51 | 0.0396 (2) | 0.61426 (15) | −0.07369 (15) | 0.0458 (6) | |
H51 | −0.0391 | 0.5901 | −0.0600 | 0.055* | |
C52 | 0.1168 (2) | 0.61240 (14) | −0.01910 (13) | 0.0400 (5) | |
H52 | 0.0906 | 0.5865 | 0.0320 | 0.048* | |
C53 | 0.2900 (2) | 0.56037 (13) | 0.10501 (13) | 0.0333 (5) | |
C54 | 0.1949 (2) | 0.57206 (15) | 0.16529 (13) | 0.0416 (6) | |
H54 | 0.1536 | 0.6291 | 0.1701 | 0.050* | |
C55 | 0.1582 (2) | 0.50188 (17) | 0.21904 (14) | 0.0491 (6) | |
H55 | 0.0926 | 0.5109 | 0.2606 | 0.059* | |
C56 | 0.2174 (2) | 0.41876 (16) | 0.21205 (16) | 0.0512 (7) | |
H56 | 0.1913 | 0.3701 | 0.2481 | 0.061* | |
C57 | 0.3135 (2) | 0.40648 (16) | 0.15313 (16) | 0.0510 (7) | |
H57 | 0.3553 | 0.3495 | 0.1490 | 0.061* | |
C58 | 0.3503 (2) | 0.47642 (14) | 0.09965 (14) | 0.0409 (5) | |
H58 | 0.4171 | 0.4673 | 0.0589 | 0.049* | |
C61 | 0.43318 (17) | 0.87835 (12) | 0.39323 (12) | 0.0274 (4) | |
C62 | 0.4555 (2) | 0.96614 (13) | 0.40321 (13) | 0.0362 (5) | |
H62 | 0.5311 | 0.9789 | 0.4177 | 0.043* | |
C63 | 0.3683 (2) | 1.03422 (14) | 0.39221 (14) | 0.0421 (6) | |
H63 | 0.3834 | 1.0935 | 0.4001 | 0.051* | |
C64 | 0.2587 (2) | 1.01655 (14) | 0.36963 (13) | 0.0382 (5) | |
H64 | 0.1988 | 1.0636 | 0.3620 | 0.046* | |
C65 | 0.23680 (19) | 0.93080 (14) | 0.35831 (13) | 0.0358 (5) | |
H65 | 0.1619 | 0.9187 | 0.3424 | 0.043* | |
C66 | 0.32339 (18) | 0.86198 (13) | 0.36994 (13) | 0.0323 (5) | |
H66 | 0.3075 | 0.8029 | 0.3619 | 0.039* | |
C67 | 0.49244 (18) | 0.69202 (13) | 0.38414 (12) | 0.0314 (5) | |
C68 | 0.5067 (2) | 0.68119 (15) | 0.30570 (14) | 0.0437 (6) | |
H68 | 0.5455 | 0.7253 | 0.2692 | 0.052* | |
C69 | 0.4653 (2) | 0.60697 (17) | 0.27952 (16) | 0.0515 (7) | |
H69 | 0.4735 | 0.6014 | 0.2254 | 0.062* | |
C70 | 0.4124 (2) | 0.54136 (16) | 0.33182 (18) | 0.0547 (7) | |
H70 | 0.3848 | 0.4902 | 0.3140 | 0.066* | |
C71 | 0.3995 (2) | 0.55019 (15) | 0.40998 (17) | 0.0475 (6) | |
H71 | 0.3642 | 0.5045 | 0.4462 | 0.057* | |
C72 | 0.43792 (19) | 0.62524 (13) | 0.43614 (14) | 0.0373 (5) | |
H72 | 0.4269 | 0.6313 | 0.4903 | 0.045* | |
C73 | 0.51826 (18) | 0.77500 (12) | 0.51866 (12) | 0.0303 (5) | |
C74 | 0.6044 (2) | 0.72442 (14) | 0.55686 (14) | 0.0384 (5) | |
H74 | 0.6765 | 0.6990 | 0.5275 | 0.046* | |
C75 | 0.5862 (2) | 0.71091 (15) | 0.63652 (16) | 0.0484 (6) | |
H75 | 0.6455 | 0.6761 | 0.6618 | 0.058* | |
C76 | 0.4824 (3) | 0.74772 (16) | 0.67963 (15) | 0.0494 (6) | |
H76 | 0.4700 | 0.7384 | 0.7346 | 0.059* | |
C77 | 0.3965 (2) | 0.79808 (15) | 0.64295 (14) | 0.0436 (6) | |
H77 | 0.3250 | 0.8236 | 0.6728 | 0.052* | |
C78 | 0.41385 (19) | 0.81172 (13) | 0.56312 (13) | 0.0338 (5) | |
H78 | 0.3540 | 0.8465 | 0.5383 | 0.041* | |
P1 | 0.04319 (5) | 0.29002 (3) | 0.42767 (3) | 0.02937 (13) | |
P2 | −0.15137 (5) | 0.83022 (4) | 0.01710 (3) | 0.03721 (15) | |
P3 | 0.34327 (5) | 0.64773 (4) | 0.02935 (3) | 0.03533 (15) | |
P4 | 0.55178 (5) | 0.79195 (3) | 0.41311 (3) | 0.03140 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0286 (10) | 0.0243 (9) | 0.0321 (12) | −0.0046 (8) | −0.0109 (8) | −0.0001 (8) |
C2 | 0.0372 (12) | 0.0273 (10) | 0.0417 (14) | 0.0007 (8) | −0.0157 (10) | −0.0001 (9) |
C3 | 0.0565 (15) | 0.0287 (11) | 0.0456 (15) | −0.0047 (10) | −0.0283 (12) | 0.0049 (10) |
C4 | 0.0602 (16) | 0.0388 (12) | 0.0326 (14) | −0.0166 (11) | −0.0143 (11) | 0.0024 (10) |
C5 | 0.0386 (12) | 0.0468 (13) | 0.0363 (14) | −0.0101 (10) | −0.0043 (10) | −0.0081 (10) |
C6 | 0.0276 (10) | 0.0374 (11) | 0.0347 (13) | −0.0024 (8) | −0.0086 (9) | −0.0030 (9) |
C7 | 0.0275 (10) | 0.0272 (10) | 0.0235 (11) | 0.0006 (8) | −0.0044 (8) | 0.0003 (8) |
C8 | 0.0349 (11) | 0.0309 (10) | 0.0373 (13) | −0.0064 (8) | −0.0099 (9) | −0.0005 (9) |
C9 | 0.0484 (13) | 0.0217 (10) | 0.0469 (15) | −0.0010 (9) | −0.0077 (11) | 0.0003 (9) |
C10 | 0.0412 (13) | 0.0314 (11) | 0.0379 (13) | 0.0099 (9) | −0.0067 (10) | 0.0018 (9) |
C11 | 0.0318 (11) | 0.0389 (12) | 0.0418 (14) | 0.0035 (9) | −0.0135 (10) | −0.0025 (10) |
C12 | 0.0322 (11) | 0.0249 (10) | 0.0406 (13) | 0.0000 (8) | −0.0099 (9) | −0.0022 (9) |
C13 | 0.0282 (10) | 0.0278 (10) | 0.0307 (12) | 0.0104 (8) | −0.0068 (8) | −0.0027 (8) |
C14 | 0.0434 (13) | 0.0311 (11) | 0.0337 (13) | 0.0033 (9) | −0.0088 (10) | −0.0010 (9) |
C15 | 0.0550 (15) | 0.0305 (11) | 0.0513 (17) | −0.0016 (10) | −0.0152 (12) | 0.0019 (10) |
C16 | 0.0593 (16) | 0.0333 (12) | 0.0576 (18) | 0.0073 (11) | −0.0269 (13) | −0.0119 (11) |
C17 | 0.0548 (15) | 0.0431 (13) | 0.0374 (14) | 0.0119 (11) | −0.0171 (11) | −0.0100 (11) |
C18 | 0.0412 (12) | 0.0358 (11) | 0.0311 (13) | 0.0094 (9) | −0.0091 (9) | −0.0003 (9) |
C21 | 0.0357 (12) | 0.0446 (12) | 0.0327 (13) | 0.0011 (9) | −0.0116 (9) | −0.0036 (10) |
C22 | 0.0474 (14) | 0.0480 (14) | 0.0544 (17) | 0.0018 (11) | −0.0140 (12) | −0.0009 (12) |
C23 | 0.0665 (19) | 0.0508 (16) | 0.085 (2) | 0.0059 (13) | −0.0307 (18) | −0.0188 (15) |
C24 | 0.072 (2) | 0.074 (2) | 0.077 (2) | 0.0225 (16) | −0.0396 (18) | −0.0467 (18) |
C25 | 0.071 (2) | 0.098 (2) | 0.0389 (17) | 0.0142 (17) | −0.0062 (14) | −0.0275 (16) |
C26 | 0.0558 (16) | 0.0658 (17) | 0.0385 (15) | −0.0070 (13) | 0.0017 (12) | −0.0133 (12) |
C27 | 0.0431 (12) | 0.0324 (11) | 0.0281 (12) | −0.0005 (9) | −0.0052 (9) | −0.0002 (9) |
C28 | 0.0444 (13) | 0.0578 (14) | 0.0333 (14) | 0.0067 (11) | −0.0066 (10) | −0.0069 (11) |
C29 | 0.0457 (14) | 0.0616 (16) | 0.0535 (17) | 0.0135 (12) | −0.0162 (12) | −0.0123 (13) |
C30 | 0.0648 (17) | 0.0454 (13) | 0.0414 (16) | 0.0035 (12) | −0.0255 (12) | −0.0024 (11) |
C31 | 0.0717 (17) | 0.0393 (12) | 0.0295 (13) | 0.0059 (11) | −0.0114 (12) | −0.0038 (10) |
C32 | 0.0484 (13) | 0.0371 (12) | 0.0306 (13) | 0.0040 (10) | −0.0024 (10) | −0.0010 (10) |
C33 | 0.0328 (11) | 0.0421 (12) | 0.0301 (12) | 0.0090 (9) | −0.0047 (9) | −0.0033 (9) |
C34 | 0.0498 (14) | 0.0392 (12) | 0.0345 (13) | 0.0053 (10) | −0.0129 (10) | −0.0059 (10) |
C35 | 0.0683 (17) | 0.0368 (13) | 0.0505 (17) | −0.0025 (11) | −0.0100 (13) | −0.0078 (11) |
C36 | 0.0607 (17) | 0.0407 (13) | 0.0525 (17) | 0.0121 (12) | −0.0009 (13) | 0.0062 (12) |
C37 | 0.0518 (16) | 0.0766 (19) | 0.0490 (17) | 0.0146 (14) | −0.0129 (13) | 0.0166 (15) |
C38 | 0.0416 (14) | 0.0712 (17) | 0.0484 (16) | −0.0020 (12) | −0.0163 (11) | 0.0107 (13) |
C41 | 0.0397 (12) | 0.0309 (10) | 0.0252 (12) | −0.0057 (9) | −0.0069 (9) | 0.0033 (9) |
C42 | 0.0417 (13) | 0.0450 (13) | 0.0464 (15) | −0.0014 (10) | −0.0142 (11) | −0.0039 (11) |
C43 | 0.0584 (16) | 0.0491 (14) | 0.0529 (17) | −0.0112 (12) | −0.0208 (13) | −0.0119 (12) |
C44 | 0.0679 (17) | 0.0302 (11) | 0.0415 (15) | −0.0022 (11) | −0.0106 (12) | −0.0041 (10) |
C45 | 0.0530 (14) | 0.0361 (12) | 0.0440 (15) | 0.0061 (10) | −0.0119 (11) | 0.0001 (10) |
C46 | 0.0432 (13) | 0.0380 (12) | 0.0369 (14) | −0.0007 (9) | −0.0134 (10) | −0.0026 (10) |
C47 | 0.0464 (13) | 0.0251 (10) | 0.0286 (12) | 0.0024 (9) | −0.0062 (9) | −0.0045 (8) |
C48 | 0.0522 (14) | 0.0401 (12) | 0.0319 (13) | −0.0082 (10) | −0.0065 (10) | 0.0023 (10) |
C49 | 0.0760 (18) | 0.0437 (13) | 0.0324 (14) | −0.0060 (12) | −0.0144 (12) | 0.0077 (11) |
C50 | 0.0633 (16) | 0.0378 (12) | 0.0434 (15) | 0.0055 (11) | −0.0260 (12) | −0.0030 (11) |
C51 | 0.0472 (14) | 0.0437 (13) | 0.0482 (16) | 0.0005 (10) | −0.0122 (11) | −0.0076 (11) |
C52 | 0.0480 (13) | 0.0409 (12) | 0.0298 (13) | −0.0031 (10) | −0.0038 (10) | −0.0008 (10) |
C53 | 0.0406 (12) | 0.0325 (11) | 0.0289 (12) | −0.0002 (9) | −0.0132 (9) | −0.0017 (9) |
C54 | 0.0494 (14) | 0.0422 (12) | 0.0305 (13) | 0.0056 (10) | −0.0048 (10) | 0.0016 (10) |
C55 | 0.0508 (15) | 0.0602 (15) | 0.0346 (14) | −0.0047 (12) | −0.0076 (11) | 0.0070 (12) |
C56 | 0.0624 (17) | 0.0462 (14) | 0.0505 (17) | −0.0175 (12) | −0.0314 (13) | 0.0172 (12) |
C57 | 0.0633 (17) | 0.0354 (12) | 0.0580 (18) | 0.0029 (11) | −0.0250 (14) | −0.0002 (12) |
C58 | 0.0438 (13) | 0.0370 (12) | 0.0433 (14) | 0.0034 (9) | −0.0128 (10) | −0.0045 (10) |
C61 | 0.0278 (10) | 0.0275 (10) | 0.0261 (11) | −0.0004 (8) | −0.0044 (8) | 0.0002 (8) |
C62 | 0.0355 (12) | 0.0336 (11) | 0.0414 (14) | −0.0066 (9) | −0.0111 (10) | 0.0000 (10) |
C63 | 0.0508 (14) | 0.0259 (10) | 0.0494 (15) | −0.0022 (9) | −0.0096 (11) | 0.0005 (10) |
C64 | 0.0421 (13) | 0.0325 (11) | 0.0365 (13) | 0.0098 (9) | −0.0058 (10) | 0.0047 (9) |
C65 | 0.0324 (11) | 0.0379 (11) | 0.0378 (13) | 0.0035 (9) | −0.0117 (9) | −0.0010 (10) |
C66 | 0.0322 (11) | 0.0287 (10) | 0.0373 (13) | −0.0003 (8) | −0.0105 (9) | −0.0024 (9) |
C67 | 0.0271 (10) | 0.0320 (10) | 0.0347 (13) | 0.0125 (8) | −0.0080 (9) | −0.0063 (9) |
C68 | 0.0478 (14) | 0.0442 (13) | 0.0370 (14) | 0.0126 (10) | −0.0081 (11) | −0.0020 (11) |
C69 | 0.0600 (16) | 0.0505 (15) | 0.0483 (16) | 0.0204 (12) | −0.0228 (13) | −0.0190 (12) |
C70 | 0.0609 (17) | 0.0383 (13) | 0.073 (2) | 0.0163 (12) | −0.0333 (14) | −0.0227 (13) |
C71 | 0.0496 (15) | 0.0369 (12) | 0.0589 (18) | 0.0010 (10) | −0.0169 (12) | −0.0068 (11) |
C72 | 0.0367 (12) | 0.0334 (11) | 0.0415 (14) | 0.0042 (9) | −0.0066 (10) | −0.0067 (10) |
C73 | 0.0310 (11) | 0.0272 (10) | 0.0354 (13) | −0.0050 (8) | −0.0119 (9) | −0.0016 (9) |
C74 | 0.0375 (12) | 0.0326 (11) | 0.0474 (15) | −0.0009 (9) | −0.0178 (10) | 0.0028 (10) |
C75 | 0.0576 (16) | 0.0386 (12) | 0.0536 (17) | −0.0100 (11) | −0.0293 (13) | 0.0134 (12) |
C76 | 0.0682 (18) | 0.0510 (14) | 0.0335 (14) | −0.0275 (13) | −0.0163 (12) | 0.0060 (11) |
C77 | 0.0488 (14) | 0.0452 (13) | 0.0382 (14) | −0.0150 (10) | −0.0031 (11) | −0.0084 (11) |
C78 | 0.0339 (11) | 0.0346 (11) | 0.0340 (13) | −0.0031 (9) | −0.0081 (9) | −0.0028 (9) |
P1 | 0.0250 (3) | 0.0309 (3) | 0.0311 (3) | 0.0030 (2) | −0.0056 (2) | 0.0015 (2) |
P2 | 0.0341 (3) | 0.0471 (3) | 0.0290 (3) | 0.0004 (2) | −0.0025 (2) | −0.0025 (2) |
P3 | 0.0415 (3) | 0.0350 (3) | 0.0287 (3) | −0.0001 (2) | −0.0051 (2) | −0.0011 (2) |
P4 | 0.0244 (3) | 0.0340 (3) | 0.0345 (3) | 0.0030 (2) | −0.0055 (2) | 0.0011 (2) |
C1—C6 | 1.389 (3) | C41—C46 | 1.392 (3) |
C1—C2 | 1.398 (3) | C41—C42 | 1.393 (3) |
C1—P1 | 1.825 (2) | C41—P3 | 1.834 (2) |
C2—C3 | 1.373 (3) | C42—C43 | 1.387 (4) |
C3—C4 | 1.380 (4) | C43—C44 | 1.378 (4) |
C4—C5 | 1.378 (3) | C44—C45 | 1.374 (4) |
C5—C6 | 1.380 (3) | C45—C46 | 1.385 (3) |
C7—C8 | 1.396 (3) | C47—C52 | 1.383 (3) |
C7—C12 | 1.396 (3) | C47—C48 | 1.392 (3) |
C7—P1 | 1.8265 (19) | C47—P3 | 1.835 (2) |
C8—C9 | 1.381 (3) | C48—C49 | 1.377 (3) |
C9—C10 | 1.381 (3) | C49—C50 | 1.371 (4) |
C10—C11 | 1.381 (3) | C50—C51 | 1.373 (3) |
C11—C12 | 1.382 (3) | C51—C52 | 1.382 (3) |
C13—C14 | 1.388 (3) | C53—C54 | 1.375 (3) |
C13—C18 | 1.391 (3) | C53—C58 | 1.393 (3) |
C13—P1 | 1.836 (2) | C53—P3 | 1.833 (2) |
C14—C15 | 1.390 (3) | C54—C55 | 1.384 (3) |
C15—C16 | 1.373 (4) | C55—C56 | 1.379 (4) |
C16—C17 | 1.375 (3) | C56—C57 | 1.368 (4) |
C17—C18 | 1.377 (3) | C57—C58 | 1.380 (3) |
C21—C26 | 1.378 (3) | C61—C66 | 1.387 (3) |
C21—C22 | 1.388 (3) | C61—C62 | 1.399 (3) |
C21—P2 | 1.831 (2) | C61—P4 | 1.8309 (19) |
C22—C23 | 1.371 (4) | C62—C63 | 1.378 (3) |
C23—C24 | 1.362 (5) | C63—C64 | 1.385 (3) |
C24—C25 | 1.371 (4) | C64—C65 | 1.374 (3) |
C25—C26 | 1.391 (4) | C65—C66 | 1.384 (3) |
C27—C28 | 1.390 (3) | C67—C68 | 1.384 (3) |
C27—C32 | 1.391 (3) | C67—C72 | 1.392 (3) |
C27—P2 | 1.827 (2) | C67—P4 | 1.837 (2) |
C28—C29 | 1.373 (3) | C68—C69 | 1.387 (4) |
C29—C30 | 1.380 (4) | C69—C70 | 1.376 (4) |
C30—C31 | 1.368 (4) | C70—C71 | 1.374 (4) |
C31—C32 | 1.383 (3) | C71—C72 | 1.383 (3) |
C33—C34 | 1.386 (3) | C73—C78 | 1.391 (3) |
C33—C38 | 1.387 (3) | C73—C74 | 1.394 (3) |
C33—P2 | 1.825 (2) | C73—P4 | 1.824 (2) |
C34—C35 | 1.388 (3) | C74—C75 | 1.376 (3) |
C35—C36 | 1.370 (4) | C75—C76 | 1.376 (4) |
C36—C37 | 1.374 (4) | C76—C77 | 1.376 (4) |
C37—C38 | 1.376 (4) | C77—C78 | 1.379 (3) |
C6—C1—C2 | 118.5 (2) | C44—C45—C46 | 120.7 (2) |
C6—C1—P1 | 123.67 (15) | C45—C46—C41 | 120.3 (2) |
C2—C1—P1 | 117.74 (16) | C52—C47—C48 | 117.9 (2) |
C3—C2—C1 | 120.7 (2) | C52—C47—P3 | 125.69 (16) |
C2—C3—C4 | 119.9 (2) | C48—C47—P3 | 116.42 (17) |
C5—C4—C3 | 120.2 (2) | C49—C48—C47 | 120.6 (2) |
C4—C5—C6 | 120.0 (2) | C50—C49—C48 | 120.6 (2) |
C5—C6—C1 | 120.6 (2) | C49—C50—C51 | 119.8 (2) |
C8—C7—C12 | 118.33 (17) | C50—C51—C52 | 119.7 (2) |
C8—C7—P1 | 117.59 (15) | C51—C52—C47 | 121.5 (2) |
C12—C7—P1 | 124.07 (15) | C54—C53—C58 | 118.53 (19) |
C9—C8—C7 | 120.6 (2) | C54—C53—P3 | 124.59 (16) |
C10—C9—C8 | 120.30 (19) | C58—C53—P3 | 116.87 (17) |
C9—C10—C11 | 119.79 (18) | C53—C54—C55 | 121.0 (2) |
C10—C11—C12 | 120.2 (2) | C56—C55—C54 | 119.8 (2) |
C11—C12—C7 | 120.69 (19) | C57—C56—C55 | 119.9 (2) |
C14—C13—C18 | 117.9 (2) | C56—C57—C58 | 120.4 (2) |
C14—C13—P1 | 124.65 (17) | C57—C58—C53 | 120.4 (2) |
C18—C13—P1 | 117.45 (15) | C66—C61—C62 | 118.57 (17) |
C13—C14—C15 | 120.7 (2) | C66—C61—P4 | 124.23 (15) |
C16—C15—C14 | 120.3 (2) | C62—C61—P4 | 117.19 (15) |
C15—C16—C17 | 119.6 (2) | C63—C62—C61 | 120.4 (2) |
C16—C17—C18 | 120.3 (2) | C62—C63—C64 | 120.2 (2) |
C17—C18—C13 | 121.2 (2) | C65—C64—C63 | 119.86 (19) |
C26—C21—C22 | 118.3 (2) | C64—C65—C66 | 120.3 (2) |
C26—C21—P2 | 124.76 (19) | C65—C66—C61 | 120.65 (19) |
C22—C21—P2 | 116.90 (18) | C68—C67—C72 | 118.1 (2) |
C23—C22—C21 | 121.7 (3) | C68—C67—P4 | 117.77 (17) |
C24—C23—C22 | 119.3 (3) | C72—C67—P4 | 124.12 (18) |
C23—C24—C25 | 120.6 (3) | C67—C68—C69 | 121.0 (2) |
C24—C25—C26 | 120.1 (3) | C70—C69—C68 | 120.1 (3) |
C21—C26—C25 | 120.0 (3) | C71—C70—C69 | 119.7 (2) |
C28—C27—C32 | 118.2 (2) | C70—C71—C72 | 120.3 (2) |
C28—C27—P2 | 124.96 (18) | C71—C72—C67 | 120.8 (2) |
C32—C27—P2 | 116.86 (16) | C78—C73—C74 | 118.3 (2) |
C29—C28—C27 | 121.0 (2) | C78—C73—P4 | 123.82 (16) |
C28—C29—C30 | 120.1 (2) | C74—C73—P4 | 117.84 (17) |
C31—C30—C29 | 119.9 (2) | C75—C74—C73 | 120.8 (2) |
C30—C31—C32 | 120.3 (2) | C76—C75—C74 | 120.1 (2) |
C31—C32—C27 | 120.6 (2) | C75—C76—C77 | 119.9 (2) |
C34—C33—C38 | 117.9 (2) | C76—C77—C78 | 120.3 (2) |
C34—C33—P2 | 124.94 (17) | C77—C78—C73 | 120.5 (2) |
C38—C33—P2 | 117.12 (19) | C1—P1—C7 | 102.22 (9) |
C33—C34—C35 | 120.9 (2) | C1—P1—C13 | 102.68 (9) |
C36—C35—C34 | 120.1 (3) | C7—P1—C13 | 102.38 (9) |
C35—C36—C37 | 119.8 (2) | C33—P2—C27 | 102.59 (10) |
C36—C37—C38 | 120.2 (2) | C33—P2—C21 | 102.28 (10) |
C37—C38—C33 | 121.2 (3) | C27—P2—C21 | 102.06 (10) |
C46—C41—C42 | 118.4 (2) | C53—P3—C41 | 102.58 (10) |
C46—C41—P3 | 124.74 (17) | C53—P3—C47 | 102.21 (10) |
C42—C41—P3 | 116.90 (16) | C41—P3—C47 | 102.49 (10) |
C43—C42—C41 | 120.8 (2) | C73—P4—C61 | 101.16 (9) |
C44—C43—C42 | 120.0 (2) | C73—P4—C67 | 101.95 (9) |
C45—C44—C43 | 119.8 (2) | C61—P4—C67 | 102.36 (9) |
C6—C1—C2—C3 | 0.5 (3) | C66—C61—C62—C63 | 1.8 (3) |
P1—C1—C2—C3 | 177.28 (16) | P4—C61—C62—C63 | −177.50 (17) |
C1—C2—C3—C4 | 0.2 (3) | C61—C62—C63—C64 | −1.3 (3) |
C2—C3—C4—C5 | −0.8 (3) | C62—C63—C64—C65 | 0.1 (3) |
C3—C4—C5—C6 | 0.6 (3) | C63—C64—C65—C66 | 0.5 (3) |
C4—C5—C6—C1 | 0.1 (3) | C64—C65—C66—C61 | 0.1 (3) |
C2—C1—C6—C5 | −0.7 (3) | C62—C61—C66—C65 | −1.2 (3) |
P1—C1—C6—C5 | −177.25 (16) | P4—C61—C66—C65 | 178.05 (16) |
C12—C7—C8—C9 | 1.2 (3) | C72—C67—C68—C69 | 1.5 (3) |
P1—C7—C8—C9 | −179.07 (17) | P4—C67—C68—C69 | 179.37 (17) |
C7—C8—C9—C10 | −1.2 (3) | C67—C68—C69—C70 | −2.0 (3) |
C8—C9—C10—C11 | 0.3 (3) | C68—C69—C70—C71 | 0.7 (4) |
C9—C10—C11—C12 | 0.6 (3) | C69—C70—C71—C72 | 0.9 (4) |
C10—C11—C12—C7 | −0.5 (3) | C70—C71—C72—C67 | −1.4 (3) |
C8—C7—C12—C11 | −0.3 (3) | C68—C67—C72—C71 | 0.2 (3) |
P1—C7—C12—C11 | 179.97 (16) | P4—C67—C72—C71 | −177.54 (16) |
C18—C13—C14—C15 | 0.3 (3) | C78—C73—C74—C75 | 0.2 (3) |
P1—C13—C14—C15 | −177.15 (16) | P4—C73—C74—C75 | 178.38 (17) |
C13—C14—C15—C16 | −1.2 (3) | C73—C74—C75—C76 | −0.2 (3) |
C14—C15—C16—C17 | 1.1 (3) | C74—C75—C76—C77 | 0.0 (4) |
C15—C16—C17—C18 | −0.2 (3) | C75—C76—C77—C78 | 0.2 (4) |
C16—C17—C18—C13 | −0.6 (3) | C76—C77—C78—C73 | −0.1 (3) |
C14—C13—C18—C17 | 0.6 (3) | C74—C73—C78—C77 | −0.1 (3) |
P1—C13—C18—C17 | 178.23 (16) | P4—C73—C78—C77 | −178.07 (16) |
C26—C21—C22—C23 | −1.2 (4) | C6—C1—P1—C7 | 9.21 (19) |
P2—C21—C22—C23 | −178.9 (2) | C2—C1—P1—C7 | −167.38 (16) |
C21—C22—C23—C24 | 1.5 (4) | C6—C1—P1—C13 | −96.67 (18) |
C22—C23—C24—C25 | −1.1 (4) | C2—C1—P1—C13 | 86.74 (17) |
C23—C24—C25—C26 | 0.3 (5) | C8—C7—P1—C1 | 83.83 (17) |
C22—C21—C26—C25 | 0.3 (4) | C12—C7—P1—C1 | −96.47 (19) |
P2—C21—C26—C25 | 177.9 (2) | C8—C7—P1—C13 | −170.05 (16) |
C24—C25—C26—C21 | 0.1 (4) | C12—C7—P1—C13 | 9.6 (2) |
C32—C27—C28—C29 | −0.2 (3) | C14—C13—P1—C1 | −1.42 (19) |
P2—C27—C28—C29 | 179.63 (19) | C18—C13—P1—C1 | −178.87 (15) |
C27—C28—C29—C30 | −0.1 (4) | C14—C13—P1—C7 | −107.17 (17) |
C28—C29—C30—C31 | 0.6 (4) | C18—C13—P1—C7 | 75.37 (16) |
C29—C30—C31—C32 | −0.9 (4) | C34—C33—P2—C27 | 7.4 (2) |
C30—C31—C32—C27 | 0.6 (3) | C38—C33—P2—C27 | −176.03 (19) |
C28—C27—C32—C31 | −0.1 (3) | C34—C33—P2—C21 | 112.9 (2) |
P2—C27—C32—C31 | −179.93 (17) | C38—C33—P2—C21 | −70.5 (2) |
C38—C33—C34—C35 | 0.7 (3) | C28—C27—P2—C33 | 80.0 (2) |
P2—C33—C34—C35 | 177.27 (18) | C32—C27—P2—C33 | −100.15 (18) |
C33—C34—C35—C36 | 0.1 (4) | C28—C27—P2—C21 | −25.7 (2) |
C34—C35—C36—C37 | −0.3 (4) | C32—C27—P2—C21 | 154.15 (17) |
C35—C36—C37—C38 | −0.4 (4) | C26—C21—P2—C33 | −10.0 (2) |
C36—C37—C38—C33 | 1.4 (4) | C22—C21—P2—C33 | 167.51 (17) |
C34—C33—C38—C37 | −1.5 (4) | C26—C21—P2—C27 | 95.9 (2) |
P2—C33—C38—C37 | −178.3 (2) | C22—C21—P2—C27 | −86.56 (19) |
C46—C41—C42—C43 | 0.5 (3) | C54—C53—P3—C41 | 24.7 (2) |
P3—C41—C42—C43 | 179.60 (19) | C58—C53—P3—C41 | −156.02 (18) |
C41—C42—C43—C44 | −0.5 (4) | C54—C53—P3—C47 | −81.2 (2) |
C42—C43—C44—C45 | 0.5 (4) | C58—C53—P3—C47 | 98.02 (19) |
C43—C44—C45—C46 | −0.5 (4) | C46—C41—P3—C53 | −92.20 (19) |
C44—C45—C46—C41 | 0.5 (3) | C42—C41—P3—C53 | 88.78 (18) |
C42—C41—C46—C45 | −0.5 (3) | C46—C41—P3—C47 | 13.5 (2) |
P3—C41—C46—C45 | −179.51 (17) | C42—C41—P3—C47 | −165.47 (16) |
C52—C47—C48—C49 | 0.7 (3) | C52—C47—P3—C53 | 19.3 (2) |
P3—C47—C48—C49 | 179.63 (18) | C48—C47—P3—C53 | −159.52 (17) |
C47—C48—C49—C50 | −1.2 (4) | C52—C47—P3—C41 | −86.7 (2) |
C48—C49—C50—C51 | 1.2 (4) | C48—C47—P3—C41 | 94.44 (18) |
C49—C50—C51—C52 | −0.8 (4) | C78—C73—P4—C61 | 9.4 (2) |
C50—C51—C52—C47 | 0.3 (3) | C74—C73—P4—C61 | −168.67 (16) |
C48—C47—C52—C51 | −0.3 (3) | C78—C73—P4—C67 | −96.00 (19) |
P3—C47—C52—C51 | −179.10 (17) | C74—C73—P4—C67 | 85.98 (17) |
C58—C53—C54—C55 | −0.9 (4) | C66—C61—P4—C73 | −99.16 (19) |
P3—C53—C54—C55 | 178.34 (19) | C62—C61—P4—C73 | 80.15 (18) |
C53—C54—C55—C56 | −0.3 (4) | C66—C61—P4—C67 | 5.9 (2) |
C54—C55—C56—C57 | 1.4 (4) | C62—C61—P4—C67 | −174.83 (17) |
C55—C56—C57—C58 | −1.3 (4) | C68—C67—P4—C73 | −177.86 (16) |
C56—C57—C58—C53 | 0.1 (4) | C72—C67—P4—C73 | −0.14 (19) |
C54—C53—C58—C57 | 1.0 (4) | C68—C67—P4—C61 | 77.72 (17) |
P3—C53—C58—C57 | −178.27 (19) | C72—C67—P4—C61 | −104.56 (17) |
C18H15PS | Z = 4 |
Mr = 294.33 | F(000) = 616 |
Triclinic, P1 | Dx = 1.303 Mg m−3 |
a = 9.542 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.207 (3) Å | Cell parameters from 5000 reflections |
c = 14.537 (4) Å | θ = 2.5–25.0° |
α = 88.89 (4)° | µ = 0.31 mm−1 |
β = 80.39 (4)° | T = 180 K |
γ = 78.28 (3)° | Prism, yellow |
V = 1500.5 (8) Å3 | 0.72 × 0.38 × 0.11 mm |
Stoe IPDS diffractometer | 5111 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 4117 reflections with I > 2σ(I) |
Planar graphite monochromator | Rint = 0.050 |
Detector resolution: 6.667 pixels mm-1 | θmax = 25.2°, θmin = 2.2° |
ϕ–oscill.,ϕ–incr.=1.5°,160 exposures scans | h = −11→11 |
Absorption correction: part of the refinement model (ΔF) see _publ_section_exptl_prep | k = −13→13 |
Tmin = 0.808, Tmax = 0.967 | l = −17→17 |
13389 measured 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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | All H-atom parameters refined |
S = 0.97 | Calculated w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3 |
5111 reflections | (Δ/σ)max = 0.044 |
481 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C18H15PS | γ = 78.28 (3)° |
Mr = 294.33 | V = 1500.5 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.542 (3) Å | Mo Kα radiation |
b = 11.207 (3) Å | µ = 0.31 mm−1 |
c = 14.537 (4) Å | T = 180 K |
α = 88.89 (4)° | 0.72 × 0.38 × 0.11 mm |
β = 80.39 (4)° |
Stoe IPDS diffractometer | 5111 independent reflections |
Absorption correction: part of the refinement model (ΔF) see _publ_section_exptl_prep | 4117 reflections with I > 2σ(I) |
Tmin = 0.808, Tmax = 0.967 | Rint = 0.050 |
13389 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.079 | All H-atom parameters refined |
S = 0.97 | Δρmax = 0.30 e Å−3 |
5111 reflections | Δρmin = −0.29 e Å−3 |
481 parameters |
Experimental. see _publ_section_exptl_prep |
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 | ||
C1 | 0.22582 (16) | 0.62962 (14) | 0.31064 (11) | 0.0241 (3) | |
C2 | 0.36131 (18) | 0.55387 (16) | 0.31099 (13) | 0.0318 (4) | |
H2 | 0.421 (2) | 0.5759 (17) | 0.3497 (14) | 0.035 (5)* | |
C3 | 0.40196 (19) | 0.44911 (17) | 0.25548 (14) | 0.0384 (5) | |
H3 | 0.491 (2) | 0.3964 (19) | 0.2570 (15) | 0.047 (6)* | |
C4 | 0.3105 (2) | 0.41927 (16) | 0.20003 (15) | 0.0413 (5) | |
H4 | 0.337 (2) | 0.350 (2) | 0.1584 (17) | 0.054 (6)* | |
C5 | 0.1760 (2) | 0.49435 (16) | 0.19882 (15) | 0.0368 (4) | |
H5 | 0.117 (2) | 0.4772 (19) | 0.1616 (16) | 0.043 (6)* | |
C6 | 0.13372 (18) | 0.59902 (15) | 0.25490 (12) | 0.0300 (4) | |
H6 | 0.037 (2) | 0.6477 (18) | 0.2528 (14) | 0.042 (5)* | |
C7 | 0.15475 (16) | 0.89539 (14) | 0.30651 (11) | 0.0235 (3) | |
C8 | 0.17863 (17) | 0.88283 (15) | 0.20978 (12) | 0.0265 (4) | |
H8 | 0.1987 (19) | 0.8071 (17) | 0.1798 (13) | 0.027 (4)* | |
C9 | 0.17046 (18) | 0.98532 (16) | 0.15429 (13) | 0.0313 (4) | |
H9 | 0.185 (2) | 0.9766 (18) | 0.0909 (16) | 0.039 (5)* | |
C10 | 0.13903 (18) | 1.10039 (16) | 0.19458 (14) | 0.0329 (4) | |
H10 | 0.132 (2) | 1.1684 (18) | 0.1524 (14) | 0.038 (5)* | |
C11 | 0.1134 (2) | 1.11366 (16) | 0.29086 (14) | 0.0351 (4) | |
H11 | 0.091 (2) | 1.193 (2) | 0.3184 (17) | 0.060 (7)* | |
C12 | 0.1217 (2) | 1.01240 (16) | 0.34700 (13) | 0.0328 (4) | |
H12 | 0.106 (2) | 1.0197 (18) | 0.4115 (16) | 0.042 (5)* | |
C13 | −0.01018 (17) | 0.75894 (14) | 0.44168 (11) | 0.0238 (3) | |
C14 | −0.02360 (19) | 0.66488 (15) | 0.50483 (12) | 0.0304 (4) | |
H14 | 0.066 (2) | 0.6078 (18) | 0.5192 (14) | 0.039 (5)* | |
C15 | −0.1589 (2) | 0.65187 (16) | 0.54954 (13) | 0.0351 (4) | |
H15 | −0.170 (2) | 0.5912 (17) | 0.5932 (14) | 0.036 (5)* | |
C16 | −0.2812 (2) | 0.73277 (17) | 0.53178 (13) | 0.0365 (4) | |
H16 | −0.380 (2) | 0.7247 (19) | 0.5602 (16) | 0.050 (6)* | |
C17 | −0.26920 (19) | 0.82675 (17) | 0.47084 (13) | 0.0355 (4) | |
H17 | −0.356 (2) | 0.8862 (18) | 0.4599 (15) | 0.043 (5)* | |
C18 | −0.13345 (18) | 0.84070 (16) | 0.42495 (12) | 0.0299 (4) | |
H18 | −0.1261 (19) | 0.9063 (17) | 0.3819 (14) | 0.031 (5)* | |
C21 | 0.40168 (16) | 0.26181 (13) | 0.94533 (10) | 0.0200 (3) | |
C22 | 0.43122 (17) | 0.16715 (14) | 1.00764 (11) | 0.0255 (4) | |
H22 | 0.3673 (19) | 0.1072 (17) | 1.0173 (13) | 0.032 (5)* | |
C23 | 0.54799 (19) | 0.15737 (15) | 1.05378 (12) | 0.0303 (4) | |
H23 | 0.568 (2) | 0.0929 (18) | 1.0932 (14) | 0.036 (5)* | |
C24 | 0.6367 (2) | 0.24171 (16) | 1.03854 (13) | 0.0323 (4) | |
H24 | 0.717 (2) | 0.2389 (18) | 1.0669 (15) | 0.044 (6)* | |
C25 | 0.60755 (19) | 0.33573 (16) | 0.97767 (13) | 0.0315 (4) | |
H25 | 0.666 (2) | 0.3951 (19) | 0.9710 (15) | 0.041 (5)* | |
C26 | 0.49071 (17) | 0.34669 (14) | 0.93081 (11) | 0.0257 (4) | |
H26 | 0.4732 (19) | 0.4137 (17) | 0.8911 (14) | 0.031 (5)* | |
C27 | 0.30204 (15) | 0.13043 (13) | 0.81150 (11) | 0.0198 (3) | |
C28 | 0.44054 (17) | 0.10100 (15) | 0.75772 (12) | 0.0262 (4) | |
H28 | 0.5088 (18) | 0.1541 (15) | 0.7574 (12) | 0.025 (4)* | |
C29 | 0.47967 (19) | −0.00341 (16) | 0.70222 (13) | 0.0332 (4) | |
H29 | 0.575 (2) | −0.0222 (18) | 0.6620 (15) | 0.042 (5)* | |
C30 | 0.3827 (2) | −0.07899 (15) | 0.70013 (13) | 0.0351 (4) | |
H30 | 0.403 (2) | −0.1484 (19) | 0.6630 (15) | 0.041 (5)* | |
C31 | 0.2465 (2) | −0.05061 (15) | 0.75359 (14) | 0.0326 (4) | |
H31 | 0.179 (2) | −0.1044 (19) | 0.7527 (15) | 0.042 (5)* | |
C32 | 0.20583 (17) | 0.05352 (14) | 0.80951 (12) | 0.0255 (4) | |
H32 | 0.118 (2) | 0.0729 (15) | 0.8457 (13) | 0.026 (4)* | |
C33 | 0.23827 (15) | 0.39777 (13) | 0.81059 (11) | 0.0206 (3) | |
C34 | 0.27996 (17) | 0.38848 (14) | 0.71398 (11) | 0.0247 (3) | |
H34 | 0.3149 (19) | 0.3125 (17) | 0.6852 (13) | 0.029 (5)* | |
C35 | 0.26451 (19) | 0.49272 (15) | 0.66023 (12) | 0.0297 (4) | |
H35 | 0.295 (2) | 0.4845 (17) | 0.5950 (15) | 0.036 (5)* | |
C36 | 0.20754 (18) | 0.60609 (15) | 0.70206 (12) | 0.0291 (4) | |
H36 | 0.199 (2) | 0.6774 (18) | 0.6630 (14) | 0.039 (5)* | |
C37 | 0.16605 (17) | 0.61553 (14) | 0.79852 (12) | 0.0279 (4) | |
H37 | 0.1240 (19) | 0.6915 (17) | 0.8260 (13) | 0.032 (5)* | |
C38 | 0.18082 (17) | 0.51229 (14) | 0.85255 (12) | 0.0254 (3) | |
H38 | 0.1508 (18) | 0.5209 (15) | 0.9163 (14) | 0.027 (4)* | |
P1 | 0.17190 (4) | 0.76632 (4) | 0.38445 (3) | 0.02364 (11) | |
P21 | 0.24796 (4) | 0.26619 (3) | 0.88624 (3) | 0.01910 (10) | |
S1 | 0.30276 (5) | 0.77707 (5) | 0.47266 (3) | 0.04195 (14) | |
S21 | 0.06628 (4) | 0.27052 (4) | 0.97219 (3) | 0.03285 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0202 (7) | 0.0251 (7) | 0.0263 (8) | −0.0068 (6) | 0.0006 (7) | 0.0077 (6) |
C2 | 0.0212 (8) | 0.0382 (9) | 0.0348 (10) | −0.0068 (7) | −0.0014 (8) | 0.0122 (8) |
C3 | 0.0249 (9) | 0.0343 (9) | 0.0469 (11) | 0.0020 (8) | 0.0088 (8) | 0.0115 (8) |
C4 | 0.0410 (11) | 0.0286 (9) | 0.0462 (11) | −0.0069 (8) | 0.0156 (10) | −0.0033 (8) |
C5 | 0.0342 (10) | 0.0375 (10) | 0.0399 (10) | −0.0153 (8) | 0.0010 (9) | −0.0054 (8) |
C6 | 0.0238 (8) | 0.0300 (8) | 0.0353 (10) | −0.0060 (7) | −0.0019 (7) | 0.0001 (7) |
C7 | 0.0219 (7) | 0.0266 (8) | 0.0233 (8) | −0.0081 (6) | −0.0038 (6) | 0.0038 (6) |
C8 | 0.0269 (8) | 0.0254 (8) | 0.0247 (8) | −0.0042 (7) | 0.0009 (7) | 0.0007 (7) |
C9 | 0.0301 (8) | 0.0368 (9) | 0.0236 (9) | −0.0046 (7) | 0.0017 (7) | 0.0077 (7) |
C10 | 0.0277 (8) | 0.0281 (8) | 0.0420 (10) | −0.0061 (7) | −0.0039 (8) | 0.0116 (8) |
C11 | 0.0367 (9) | 0.0241 (8) | 0.0460 (11) | −0.0071 (7) | −0.0094 (8) | −0.0013 (8) |
C12 | 0.0400 (10) | 0.0334 (9) | 0.0275 (9) | −0.0114 (7) | −0.0075 (8) | −0.0032 (7) |
C13 | 0.0274 (8) | 0.0277 (8) | 0.0168 (7) | −0.0087 (6) | −0.0009 (6) | −0.0027 (6) |
C14 | 0.0342 (9) | 0.0269 (8) | 0.0272 (9) | −0.0051 (7) | 0.0015 (7) | 0.0015 (7) |
C15 | 0.0422 (10) | 0.0312 (9) | 0.0286 (9) | −0.0109 (8) | 0.0073 (8) | 0.0010 (7) |
C16 | 0.0319 (9) | 0.0449 (10) | 0.0306 (10) | −0.0132 (8) | 0.0084 (8) | −0.0087 (8) |
C17 | 0.0282 (9) | 0.0452 (10) | 0.0310 (9) | −0.0032 (8) | −0.0036 (7) | −0.0047 (8) |
C18 | 0.0319 (9) | 0.0350 (9) | 0.0228 (8) | −0.0063 (7) | −0.0049 (7) | 0.0028 (7) |
C21 | 0.0226 (7) | 0.0185 (7) | 0.0171 (7) | −0.0013 (6) | −0.0021 (6) | −0.0019 (6) |
C22 | 0.0315 (8) | 0.0193 (7) | 0.0259 (8) | −0.0047 (6) | −0.0058 (7) | 0.0020 (6) |
C23 | 0.0375 (9) | 0.0251 (8) | 0.0274 (9) | 0.0011 (7) | −0.0125 (7) | 0.0030 (7) |
C24 | 0.0307 (9) | 0.0354 (9) | 0.0319 (9) | −0.0019 (7) | −0.0137 (8) | −0.0057 (7) |
C25 | 0.0316 (9) | 0.0325 (9) | 0.0334 (9) | −0.0126 (7) | −0.0066 (8) | −0.0026 (7) |
C26 | 0.0307 (8) | 0.0239 (8) | 0.0228 (8) | −0.0071 (7) | −0.0040 (7) | 0.0045 (7) |
C27 | 0.0199 (7) | 0.0175 (7) | 0.0223 (7) | −0.0019 (6) | −0.0069 (6) | 0.0032 (6) |
C28 | 0.0216 (8) | 0.0266 (8) | 0.0294 (9) | −0.0036 (6) | −0.0029 (7) | −0.0005 (7) |
C29 | 0.0295 (9) | 0.0334 (9) | 0.0334 (9) | 0.0015 (7) | −0.0047 (8) | −0.0056 (7) |
C30 | 0.0440 (10) | 0.0235 (8) | 0.0378 (10) | 0.0011 (7) | −0.0155 (9) | −0.0059 (7) |
C31 | 0.0381 (9) | 0.0226 (8) | 0.0440 (10) | −0.0109 (7) | −0.0209 (9) | 0.0050 (7) |
C32 | 0.0215 (8) | 0.0243 (8) | 0.0322 (9) | −0.0052 (6) | −0.0086 (7) | 0.0068 (7) |
C33 | 0.0190 (7) | 0.0205 (7) | 0.0226 (8) | −0.0036 (6) | −0.0050 (6) | 0.0051 (6) |
C34 | 0.0276 (8) | 0.0237 (8) | 0.0227 (8) | −0.0038 (6) | −0.0054 (7) | −0.0001 (6) |
C35 | 0.0361 (9) | 0.0332 (9) | 0.0215 (9) | −0.0094 (7) | −0.0073 (7) | 0.0057 (7) |
C36 | 0.0313 (8) | 0.0255 (8) | 0.0328 (9) | −0.0074 (7) | −0.0111 (7) | 0.0115 (7) |
C37 | 0.0280 (8) | 0.0192 (8) | 0.0359 (9) | −0.0004 (6) | −0.0086 (7) | 0.0019 (7) |
C38 | 0.0261 (8) | 0.0254 (8) | 0.0226 (8) | −0.0003 (6) | −0.0032 (7) | 0.0001 (6) |
P1 | 0.0249 (2) | 0.0282 (2) | 0.0200 (2) | −0.00944 (16) | −0.00537 (16) | 0.00512 (16) |
P21 | 0.01893 (19) | 0.01805 (18) | 0.0184 (2) | −0.00135 (14) | −0.00092 (15) | 0.00284 (14) |
S1 | 0.0461 (3) | 0.0576 (3) | 0.0334 (3) | −0.0251 (2) | −0.0221 (2) | 0.0133 (2) |
S21 | 0.0244 (2) | 0.0370 (2) | 0.0303 (2) | −0.00064 (17) | 0.00723 (17) | 0.00658 (18) |
C1—C6 | 1.385 (3) | C21—C22 | 1.397 (2) |
C1—C2 | 1.396 (2) | C21—P21 | 1.8116 (17) |
C1—P1 | 1.8226 (18) | C22—C23 | 1.379 (3) |
C2—C3 | 1.388 (3) | C22—H22 | 0.99 (2) |
C2—H2 | 0.93 (2) | C23—C24 | 1.383 (3) |
C3—C4 | 1.374 (3) | C23—H23 | 0.92 (2) |
C3—H3 | 0.94 (2) | C24—C25 | 1.378 (3) |
C4—C5 | 1.387 (3) | C24—H24 | 0.93 (2) |
C4—H4 | 0.96 (2) | C25—C26 | 1.384 (3) |
C5—C6 | 1.392 (3) | C25—H25 | 0.95 (2) |
C5—H5 | 0.89 (2) | C26—H26 | 0.943 (19) |
C6—H6 | 0.98 (2) | C27—C32 | 1.385 (2) |
C7—C8 | 1.392 (2) | C27—C28 | 1.398 (2) |
C7—C12 | 1.402 (2) | C27—P21 | 1.8218 (17) |
C7—P1 | 1.8181 (17) | C28—C29 | 1.385 (2) |
C8—C9 | 1.387 (2) | C28—H28 | 0.967 (19) |
C8—H8 | 0.931 (19) | C29—C30 | 1.380 (3) |
C9—C10 | 1.382 (3) | C29—H29 | 0.98 (2) |
C9—H9 | 0.91 (2) | C30—C31 | 1.378 (3) |
C10—C11 | 1.386 (3) | C30—H30 | 0.92 (2) |
C10—H10 | 0.97 (2) | C31—C32 | 1.386 (3) |
C11—C12 | 1.382 (3) | C31—H31 | 0.97 (2) |
C11—H11 | 0.95 (2) | C32—H32 | 0.903 (18) |
C12—H12 | 0.93 (2) | C33—C34 | 1.394 (2) |
C13—C18 | 1.390 (2) | C33—C38 | 1.397 (2) |
C13—C14 | 1.396 (2) | C33—P21 | 1.8189 (16) |
C13—P1 | 1.8139 (17) | C34—C35 | 1.389 (2) |
C14—C15 | 1.380 (2) | C34—H34 | 0.929 (19) |
C14—H14 | 1.01 (2) | C35—C36 | 1.385 (3) |
C15—C16 | 1.383 (3) | C35—H35 | 0.95 (2) |
C15—H15 | 0.93 (2) | C36—C37 | 1.392 (3) |
C16—C17 | 1.373 (3) | C36—H36 | 0.97 (2) |
C16—H16 | 0.99 (2) | C37—C38 | 1.382 (2) |
C17—C18 | 1.392 (3) | C37—H37 | 0.931 (19) |
C17—H17 | 0.98 (2) | C38—H38 | 0.924 (19) |
C18—H18 | 0.963 (19) | P1—S1 | 1.9545 (9) |
C21—C26 | 1.390 (2) | P21—S21 | 1.9528 (9) |
C6—C1—C2 | 119.44 (16) | C22—C23—C24 | 119.96 (16) |
C6—C1—P1 | 120.99 (12) | C22—C23—H23 | 119.4 (13) |
C2—C1—P1 | 119.57 (15) | C24—C23—H23 | 120.6 (12) |
C3—C2—C1 | 119.6 (2) | C25—C24—C23 | 119.85 (18) |
C3—C2—H2 | 122.5 (11) | C25—C24—H24 | 116.5 (13) |
C1—C2—H2 | 117.8 (11) | C23—C24—H24 | 123.6 (13) |
C4—C3—C2 | 120.76 (17) | C24—C25—C26 | 120.83 (17) |
C4—C3—H3 | 119.1 (14) | C24—C25—H25 | 118.5 (13) |
C2—C3—H3 | 120.1 (14) | C26—C25—H25 | 120.6 (13) |
C3—C4—C5 | 120.03 (18) | C25—C26—C21 | 119.62 (15) |
C3—C4—H4 | 122.9 (14) | C25—C26—H26 | 118.0 (12) |
C5—C4—H4 | 117.0 (14) | C21—C26—H26 | 122.4 (11) |
C4—C5—C6 | 119.6 (2) | C32—C27—C28 | 119.37 (14) |
C4—C5—H5 | 120.8 (13) | C32—C27—P21 | 119.58 (12) |
C6—C5—H5 | 119.5 (13) | C28—C27—P21 | 121.03 (13) |
C1—C6—C5 | 120.52 (16) | C29—C28—C27 | 119.97 (17) |
C1—C6—H6 | 123.0 (12) | C29—C28—H28 | 119.4 (10) |
C5—C6—H6 | 116.4 (13) | C27—C28—H28 | 120.6 (10) |
C8—C7—C12 | 119.31 (15) | C30—C29—C28 | 120.24 (16) |
C8—C7—P1 | 123.14 (12) | C30—C29—H29 | 119.4 (12) |
C12—C7—P1 | 117.49 (13) | C28—C29—H29 | 120.3 (12) |
C9—C8—C7 | 120.12 (16) | C31—C30—C29 | 119.89 (16) |
C9—C8—H8 | 117.5 (11) | C31—C30—H30 | 116.5 (13) |
C7—C8—H8 | 122.4 (11) | C29—C30—H30 | 123.6 (13) |
C10—C9—C8 | 120.31 (17) | C30—C31—C32 | 120.51 (17) |
C10—C9—H9 | 119.9 (12) | C30—C31—H31 | 119.8 (12) |
C8—C9—H9 | 119.8 (13) | C32—C31—H31 | 119.7 (12) |
C9—C10—C11 | 119.89 (16) | C27—C32—C31 | 120.02 (15) |
C9—C10—H10 | 116.6 (12) | C27—C32—H32 | 118.2 (12) |
C11—C10—H10 | 123.5 (12) | C31—C32—H32 | 121.7 (12) |
C12—C11—C10 | 120.43 (17) | C34—C33—C38 | 119.52 (14) |
C12—C11—H11 | 119.9 (15) | C34—C33—P21 | 123.14 (12) |
C10—C11—H11 | 119.7 (15) | C38—C33—P21 | 117.30 (12) |
C11—C12—C7 | 119.93 (17) | C35—C34—C33 | 119.96 (15) |
C11—C12—H12 | 121.5 (13) | C35—C34—H34 | 119.8 (11) |
C7—C12—H12 | 118.6 (13) | C33—C34—H34 | 120.2 (11) |
C18—C13—C14 | 119.82 (15) | C36—C35—C34 | 120.36 (16) |
C18—C13—P1 | 123.30 (13) | C36—C35—H35 | 121.0 (11) |
C14—C13—P1 | 116.89 (12) | C34—C35—H35 | 118.6 (11) |
C15—C14—C13 | 120.19 (16) | C35—C36—C37 | 119.75 (15) |
C15—C14—H14 | 119.8 (11) | C35—C36—H36 | 118.6 (12) |
C13—C14—H14 | 120.0 (11) | C37—C36—H36 | 121.6 (12) |
C14—C15—C16 | 119.67 (17) | C38—C37—C36 | 120.29 (15) |
C14—C15—H15 | 121.2 (11) | C38—C37—H37 | 120.3 (11) |
C16—C15—H15 | 119.1 (11) | C36—C37—H37 | 119.3 (11) |
C17—C16—C15 | 120.65 (16) | C37—C38—C33 | 120.12 (15) |
C17—C16—H16 | 117.1 (12) | C37—C38—H38 | 118.6 (11) |
C15—C16—H16 | 122.3 (12) | C33—C38—H38 | 121.3 (11) |
C16—C17—C18 | 120.31 (17) | C13—P1—C7 | 106.83 (8) |
C16—C17—H17 | 120.9 (12) | C13—P1—C1 | 103.43 (8) |
C18—C17—H17 | 118.8 (12) | C7—P1—C1 | 106.60 (8) |
C13—C18—C17 | 119.36 (16) | C13—P1—S1 | 112.82 (6) |
C13—C18—H18 | 120.9 (10) | C7—P1—S1 | 112.47 (6) |
C17—C18—H18 | 119.8 (10) | C1—P1—S1 | 113.99 (6) |
C26—C21—C22 | 119.29 (15) | C21—P21—C33 | 107.11 (8) |
C26—C21—P21 | 123.21 (12) | C21—P21—C27 | 103.61 (7) |
C22—C21—P21 | 117.50 (12) | C33—P21—C27 | 107.38 (7) |
C23—C22—C21 | 120.44 (16) | C21—P21—S21 | 113.01 (5) |
C23—C22—H22 | 121.0 (11) | C33—P21—S21 | 111.97 (6) |
C21—C22—H22 | 118.6 (11) | C27—P21—S21 | 113.19 (6) |
C6—C1—C2—C3 | 0.1 (2) | C33—C34—C35—C36 | −0.1 (3) |
P1—C1—C2—C3 | 179.39 (12) | C34—C35—C36—C37 | 0.2 (3) |
C1—C2—C3—C4 | 0.1 (2) | C35—C36—C37—C38 | −0.3 (3) |
C2—C3—C4—C5 | 0.2 (3) | C36—C37—C38—C33 | 0.3 (3) |
C3—C4—C5—C6 | −0.8 (3) | C34—C33—C38—C37 | −0.2 (2) |
C2—C1—C6—C5 | −0.7 (2) | P21—C33—C38—C37 | −177.85 (13) |
P1—C1—C6—C5 | −179.96 (13) | C18—C13—P1—C7 | −0.13 (17) |
C4—C5—C6—C1 | 1.0 (3) | C14—C13—P1—C7 | 179.42 (13) |
C12—C7—C8—C9 | 0.4 (2) | C18—C13—P1—C1 | −112.40 (15) |
P1—C7—C8—C9 | −176.89 (13) | C14—C13—P1—C1 | 67.15 (14) |
C7—C8—C9—C10 | 0.2 (3) | C18—C13—P1—S1 | 123.96 (14) |
C8—C9—C10—C11 | −1.0 (3) | C14—C13—P1—S1 | −56.49 (14) |
C9—C10—C11—C12 | 1.2 (3) | C8—C7—P1—C13 | −109.31 (15) |
C10—C11—C12—C7 | −0.6 (3) | C12—C7—P1—C13 | 73.39 (15) |
C8—C7—C12—C11 | −0.1 (3) | C8—C7—P1—C1 | 0.77 (16) |
P1—C7—C12—C11 | 177.27 (14) | C12—C7—P1—C1 | −176.52 (13) |
C18—C13—C14—C15 | 1.0 (3) | C8—C7—P1—S1 | 126.39 (13) |
P1—C13—C14—C15 | −178.61 (14) | C12—C7—P1—S1 | −50.91 (14) |
C13—C14—C15—C16 | −0.3 (3) | C6—C1—P1—C13 | 47.09 (14) |
C14—C15—C16—C17 | −0.7 (3) | C2—C1—P1—C13 | −132.20 (13) |
C15—C16—C17—C18 | 1.0 (3) | C6—C1—P1—C7 | −65.35 (14) |
C14—C13—C18—C17 | −0.7 (3) | C2—C1—P1—C7 | 115.35 (13) |
P1—C13—C18—C17 | 178.85 (14) | C6—C1—P1—S1 | 169.95 (11) |
C16—C17—C18—C13 | −0.3 (3) | C2—C1—P1—S1 | −9.34 (14) |
C26—C21—C22—C23 | −0.5 (2) | C26—C21—P21—C33 | −0.41 (14) |
P21—C21—C22—C23 | 178.95 (12) | C22—C21—P21—C33 | −179.81 (11) |
C21—C22—C23—C24 | 0.1 (2) | C26—C21—P21—C27 | 112.93 (13) |
C22—C23—C24—C25 | 0.4 (3) | C22—C21—P21—C27 | −66.47 (13) |
C23—C24—C25—C26 | −0.4 (3) | C26—C21—P21—S21 | −124.19 (12) |
C24—C25—C26—C21 | 0.0 (2) | C22—C21—P21—S21 | 56.41 (12) |
C22—C21—C26—C25 | 0.4 (2) | C34—C33—P21—C21 | 105.32 (15) |
P21—C21—C26—C25 | −178.95 (12) | C38—C33—P21—C21 | −77.16 (14) |
C32—C27—C28—C29 | 0.8 (2) | C34—C33—P21—C27 | −5.43 (16) |
P21—C27—C28—C29 | 179.29 (13) | C38—C33—P21—C27 | 172.09 (12) |
C27—C28—C29—C30 | −0.3 (3) | C34—C33—P21—S21 | −130.26 (13) |
C28—C29—C30—C31 | −0.1 (3) | C38—C33—P21—S21 | 47.26 (14) |
C29—C30—C31—C32 | 0.1 (3) | C32—C27—P21—C21 | 132.71 (12) |
C28—C27—C32—C31 | −0.9 (2) | C28—C27—P21—C21 | −45.74 (14) |
P21—C27—C32—C31 | −179.35 (12) | C32—C27—P21—C33 | −114.15 (13) |
C30—C31—C32—C27 | 0.4 (2) | C28—C27—P21—C33 | 67.40 (14) |
C38—C33—C34—C35 | 0.1 (2) | C32—C27—P21—S21 | 9.95 (14) |
P21—C33—C34—C35 | 177.61 (13) | C28—C27—P21—S21 | −168.50 (11) |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C18H15P | C18H15PS |
Mr | 262.27 | 294.33 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 180 | 180 |
a, b, c (Å) | 11.0306 (19), 15.111 (3), 17.554 (3) | 9.542 (3), 11.207 (3), 14.537 (4) |
α, β, γ (°) | 84.38 (2), 80.36 (2), 85.82 (2) | 88.89 (4), 80.39 (4), 78.28 (3) |
V (Å3) | 2866.0 (8) | 1500.5 (8) |
Z | 8 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.18 | 0.31 |
Crystal size (mm) | 0.48 × 0.48 × 0.28 | 0.72 × 0.38 × 0.11 |
Data collection | ||
Diffractometer | Stoe IPDS diffractometer | Stoe IPDS diffractometer |
Absorption correction | Part of the refinement model (ΔF) see _publ_section_exptl_prep | Part of the refinement model (ΔF) see _publ_section_exptl_prep |
Tmin, Tmax | 0.921, 0.953 | 0.808, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17345, 9738, 6818 | 13389, 5111, 4117 |
Rint | 0.032 | 0.050 |
(sin θ/λ)max (Å−1) | 0.600 | 0.600 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.111, 0.92 | 0.029, 0.079, 0.97 |
No. of reflections | 9738 | 5111 |
No. of parameters | 685 | 481 |
H-atom treatment | H-atom parameters constrained | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 1.02, −0.23 | 0.30, −0.29 |
Computer programs: IPDS2.87 (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XSTEP-2.18 (Stoe & Cie, 1997).
By reaction of triphenylphosphine, (I), with pyridinedithiomonometaphosphoryl chloride, an insertion of sulfur into triphenylphosphine takes place and a new triclinic polymorph of triphenylphosphine sulfide, (II), was isolated. The analogous reaction of triphenylphosphine with pyridinedithiomonometaphosphoryl fluoride yields in addition to the abovementioned sulfide a new crystallographic modification of triclinic triphenylphosphine. Both compounds form monoclinic structures, too, which have been described previously by Howells et al. (1954) and Codding & Kerr (1978), respectively.
In the unit cell of triphenylphosphine there are four independent molecules. Here, it is obvious that the four highest peaks in the final difference electron-density map [1.08 (4), 0.69 (4), 0.64 (4) and 0.31 (4) e Å−3] are observed at the `lone-pair regions' of P1–P4. The distances between those peaks and the corresponding P atoms are 1.25, 1.35, 1.35 and 1.22 Å, respectively.