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New triclinic polymorphs of tri­phenyl­phosphine, (I), and tri­phenyl­phosphine sulfide, (II), were crystallized. For the structure of (I), it is obvious that the highest peaks in the final difference electron-density map are located at the `lone-pair regions' of P atoms. We have observed this effect in two further phosphorous-containing structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000433/qa0201sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000433/qa0201Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000433/qa0201IIsup3.hkl
Contains datablock 2

CCDC references: 142938; 142939

Comment top

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.

Experimental top

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.

Computing details top

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).

(I) Triphenylphoshine top
Crystal data top
C18H15PZ = 8
Mr = 262.27F(000) = 1104
Triclinic, P1Dx = 1.216 Mg m3
a = 11.0306 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.111 (3) ÅCell parameters from 5000 reflections
c = 17.554 (3) Åθ = 2.5–25.0°
α = 84.38 (2)°µ = 0.18 mm1
β = 80.36 (2)°T = 180 K
γ = 85.82 (2)°Block, colorless
V = 2866.0 (8) Å30.48 × 0.48 × 0.28 mm
Data collection top
Stoe IPDS
diffractometer
9738 independent reflections
Radiation source: fine-focus sealed X-ray tube6818 reflections with I > 2σ(I)
Planar graphite monochromatorRint = 0.032
Detector resolution: 6.667 pixels mm-1θmax = 25.3°, θmin = 2.3°
ϕ–oscill.,ϕ–incr.=1.4°,164 exposures scansh = 1313
Absorption correction: part of the refinement model (ΔF)
see _publ_section_exptl_prep
k = 1818
Tmin = 0.921, Tmax = 0.953l = 2020
17345 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-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 parametersΔρmax = 1.02 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C18H15Pγ = 85.82 (2)°
Mr = 262.27V = 2866.0 (8) Å3
Triclinic, P1Z = 8
a = 11.0306 (19) ÅMo Kα radiation
b = 15.111 (3) ŵ = 0.18 mm1
c = 17.554 (3) ÅT = 180 K
α = 84.38 (2)°0.48 × 0.48 × 0.28 mm
β = 80.36 (2)°
Data collection top
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 = 0.953Rint = 0.032
17345 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 0.92Δρmax = 1.02 e Å3
9738 reflectionsΔρmin = 0.23 e Å3
685 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.00732 (17)0.27383 (12)0.53322 (12)0.0277 (4)
C20.0936 (2)0.22447 (13)0.57254 (13)0.0347 (5)
H20.16610.19870.54390.042*
C30.0748 (2)0.21288 (14)0.65211 (14)0.0417 (6)
H30.13410.17940.67820.050*
C40.0305 (2)0.24995 (14)0.69410 (14)0.0428 (6)
H40.04390.24130.74910.051*
C50.1161 (2)0.29947 (15)0.65643 (14)0.0401 (5)
H50.18810.32540.68550.048*
C60.09737 (18)0.31147 (14)0.57646 (13)0.0328 (5)
H60.15660.34580.55080.039*
C70.07266 (17)0.37660 (12)0.40449 (11)0.0263 (4)
C80.04735 (19)0.46494 (13)0.40897 (13)0.0339 (5)
H80.02860.47790.42290.041*
C90.1317 (2)0.53367 (13)0.39329 (14)0.0393 (5)
H90.11410.59340.39750.047*
C100.2414 (2)0.51590 (14)0.37150 (13)0.0377 (5)
H100.29900.56330.36050.045*
C110.26716 (19)0.42895 (14)0.36574 (13)0.0370 (5)
H110.34230.41670.35030.044*
C120.18401 (18)0.35977 (13)0.38235 (13)0.0322 (5)
H120.20280.30010.37870.039*
C130.01417 (18)0.19020 (12)0.39731 (12)0.0293 (5)
C140.0675 (2)0.12202 (13)0.44773 (13)0.0362 (5)
H140.07960.12680.50210.043*
C150.1035 (2)0.04691 (14)0.41957 (15)0.0453 (6)
H150.13850.00020.45480.054*
C160.0887 (2)0.03984 (15)0.34111 (16)0.0480 (6)
H160.11470.01110.32190.058*
C170.0360 (2)0.10690 (15)0.29048 (15)0.0443 (6)
H170.02530.10220.23620.053*
C180.0013 (2)0.18089 (14)0.31816 (13)0.0364 (5)
H180.03840.22640.28250.044*
C210.2074 (2)0.91075 (15)0.08825 (13)0.0371 (5)
C220.1657 (2)0.99603 (16)0.07155 (16)0.0498 (6)
H220.11181.00970.02430.060*
C230.2002 (3)1.06103 (19)0.1214 (2)0.0648 (8)
H230.17221.11940.10830.078*
C240.2751 (3)1.0411 (2)0.1900 (2)0.0700 (9)
H240.29821.08560.22520.084*
C250.3174 (3)0.9574 (2)0.20869 (17)0.0691 (9)
H250.36990.94420.25660.083*
C260.2836 (2)0.89173 (19)0.15767 (15)0.0537 (7)
H260.31320.83380.17070.064*
C270.2621 (2)0.85088 (13)0.05018 (13)0.0349 (5)
C280.3821 (2)0.88611 (16)0.03124 (14)0.0454 (6)
H280.41150.90090.02020.054*
C290.4589 (2)0.89985 (17)0.08586 (16)0.0530 (7)
H290.54070.92390.07200.064*
C300.4173 (2)0.87874 (16)0.16084 (15)0.0490 (6)
H300.47020.88880.19870.059*
C310.2998 (2)0.84328 (15)0.18057 (14)0.0468 (6)
H310.27160.82800.23200.056*
C320.2219 (2)0.82964 (14)0.12594 (13)0.0396 (5)
H320.14020.80550.14030.048*
C330.19759 (19)0.72502 (14)0.07042 (13)0.0356 (5)
C340.2857 (2)0.67289 (14)0.05271 (14)0.0407 (5)
H340.32920.69290.01130.049*
C350.3112 (3)0.59183 (15)0.09464 (16)0.0516 (7)
H350.37170.55680.08180.062*
C360.2492 (3)0.56233 (16)0.15459 (16)0.0537 (7)
H360.26690.50700.18350.064*
C370.1614 (3)0.6131 (2)0.17281 (16)0.0610 (8)
H370.11870.59290.21460.073*
C380.1350 (2)0.69300 (18)0.13069 (15)0.0538 (7)
H380.07290.72690.14310.065*
C410.29537 (19)0.74993 (13)0.07740 (12)0.0319 (5)
C420.3783 (2)0.78111 (15)0.11877 (15)0.0436 (6)
H420.45520.74920.12120.052*
C430.3501 (2)0.85822 (16)0.15653 (16)0.0512 (6)
H430.40730.87850.18490.061*
C440.2393 (2)0.90541 (15)0.15289 (14)0.0463 (6)
H440.22010.95850.17840.056*
C450.1566 (2)0.87541 (15)0.11227 (14)0.0446 (6)
H450.07990.90780.11020.053*
C460.1838 (2)0.79848 (14)0.07436 (13)0.0387 (5)
H460.12610.77870.04610.046*
C470.2316 (2)0.64744 (13)0.03721 (12)0.0334 (5)
C480.2676 (2)0.68455 (14)0.11264 (13)0.0415 (6)
H480.34630.70850.12690.050*
C490.1902 (3)0.68685 (16)0.16678 (15)0.0507 (7)
H490.21530.71340.21780.061*
C500.0771 (2)0.65119 (15)0.14779 (15)0.0466 (6)
H500.02490.65200.18580.056*
C510.0396 (2)0.61426 (15)0.07369 (15)0.0458 (6)
H510.03910.59010.06000.055*
C520.1168 (2)0.61240 (14)0.01910 (13)0.0400 (5)
H520.09060.58650.03200.048*
C530.2900 (2)0.56037 (13)0.10501 (13)0.0333 (5)
C540.1949 (2)0.57206 (15)0.16529 (13)0.0416 (6)
H540.15360.62910.17010.050*
C550.1582 (2)0.50188 (17)0.21904 (14)0.0491 (6)
H550.09260.51090.26060.059*
C560.2174 (2)0.41876 (16)0.21205 (16)0.0512 (7)
H560.19130.37010.24810.061*
C570.3135 (2)0.40648 (16)0.15313 (16)0.0510 (7)
H570.35530.34950.14900.061*
C580.3503 (2)0.47642 (14)0.09965 (14)0.0409 (5)
H580.41710.46730.05890.049*
C610.43318 (17)0.87835 (12)0.39323 (12)0.0274 (4)
C620.4555 (2)0.96614 (13)0.40321 (13)0.0362 (5)
H620.53110.97890.41770.043*
C630.3683 (2)1.03422 (14)0.39221 (14)0.0421 (6)
H630.38341.09350.40010.051*
C640.2587 (2)1.01655 (14)0.36963 (13)0.0382 (5)
H640.19881.06360.36200.046*
C650.23680 (19)0.93080 (14)0.35831 (13)0.0358 (5)
H650.16190.91870.34240.043*
C660.32339 (18)0.86198 (13)0.36994 (13)0.0323 (5)
H660.30750.80290.36190.039*
C670.49244 (18)0.69202 (13)0.38414 (12)0.0314 (5)
C680.5067 (2)0.68119 (15)0.30570 (14)0.0437 (6)
H680.54550.72530.26920.052*
C690.4653 (2)0.60697 (17)0.27952 (16)0.0515 (7)
H690.47350.60140.22540.062*
C700.4124 (2)0.54136 (16)0.33182 (18)0.0547 (7)
H700.38480.49020.31400.066*
C710.3995 (2)0.55019 (15)0.40998 (17)0.0475 (6)
H710.36420.50450.44620.057*
C720.43792 (19)0.62524 (13)0.43614 (14)0.0373 (5)
H720.42690.63130.49030.045*
C730.51826 (18)0.77500 (12)0.51866 (12)0.0303 (5)
C740.6044 (2)0.72442 (14)0.55686 (14)0.0384 (5)
H740.67650.69900.52750.046*
C750.5862 (2)0.71091 (15)0.63652 (16)0.0484 (6)
H750.64550.67610.66180.058*
C760.4824 (3)0.74772 (16)0.67963 (15)0.0494 (6)
H760.47000.73840.73460.059*
C770.3965 (2)0.79808 (15)0.64295 (14)0.0436 (6)
H770.32500.82360.67280.052*
C780.41385 (19)0.81172 (13)0.56312 (13)0.0338 (5)
H780.35400.84650.53830.041*
P10.04319 (5)0.29002 (3)0.42767 (3)0.02937 (13)
P20.15137 (5)0.83022 (4)0.01710 (3)0.03721 (15)
P30.34327 (5)0.64773 (4)0.02935 (3)0.03533 (15)
P40.55178 (5)0.79195 (3)0.41311 (3)0.03140 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0286 (10)0.0243 (9)0.0321 (12)0.0046 (8)0.0109 (8)0.0001 (8)
C20.0372 (12)0.0273 (10)0.0417 (14)0.0007 (8)0.0157 (10)0.0001 (9)
C30.0565 (15)0.0287 (11)0.0456 (15)0.0047 (10)0.0283 (12)0.0049 (10)
C40.0602 (16)0.0388 (12)0.0326 (14)0.0166 (11)0.0143 (11)0.0024 (10)
C50.0386 (12)0.0468 (13)0.0363 (14)0.0101 (10)0.0043 (10)0.0081 (10)
C60.0276 (10)0.0374 (11)0.0347 (13)0.0024 (8)0.0086 (9)0.0030 (9)
C70.0275 (10)0.0272 (10)0.0235 (11)0.0006 (8)0.0044 (8)0.0003 (8)
C80.0349 (11)0.0309 (10)0.0373 (13)0.0064 (8)0.0099 (9)0.0005 (9)
C90.0484 (13)0.0217 (10)0.0469 (15)0.0010 (9)0.0077 (11)0.0003 (9)
C100.0412 (13)0.0314 (11)0.0379 (13)0.0099 (9)0.0067 (10)0.0018 (9)
C110.0318 (11)0.0389 (12)0.0418 (14)0.0035 (9)0.0135 (10)0.0025 (10)
C120.0322 (11)0.0249 (10)0.0406 (13)0.0000 (8)0.0099 (9)0.0022 (9)
C130.0282 (10)0.0278 (10)0.0307 (12)0.0104 (8)0.0068 (8)0.0027 (8)
C140.0434 (13)0.0311 (11)0.0337 (13)0.0033 (9)0.0088 (10)0.0010 (9)
C150.0550 (15)0.0305 (11)0.0513 (17)0.0016 (10)0.0152 (12)0.0019 (10)
C160.0593 (16)0.0333 (12)0.0576 (18)0.0073 (11)0.0269 (13)0.0119 (11)
C170.0548 (15)0.0431 (13)0.0374 (14)0.0119 (11)0.0171 (11)0.0100 (11)
C180.0412 (12)0.0358 (11)0.0311 (13)0.0094 (9)0.0091 (9)0.0003 (9)
C210.0357 (12)0.0446 (12)0.0327 (13)0.0011 (9)0.0116 (9)0.0036 (10)
C220.0474 (14)0.0480 (14)0.0544 (17)0.0018 (11)0.0140 (12)0.0009 (12)
C230.0665 (19)0.0508 (16)0.085 (2)0.0059 (13)0.0307 (18)0.0188 (15)
C240.072 (2)0.074 (2)0.077 (2)0.0225 (16)0.0396 (18)0.0467 (18)
C250.071 (2)0.098 (2)0.0389 (17)0.0142 (17)0.0062 (14)0.0275 (16)
C260.0558 (16)0.0658 (17)0.0385 (15)0.0070 (13)0.0017 (12)0.0133 (12)
C270.0431 (12)0.0324 (11)0.0281 (12)0.0005 (9)0.0052 (9)0.0002 (9)
C280.0444 (13)0.0578 (14)0.0333 (14)0.0067 (11)0.0066 (10)0.0069 (11)
C290.0457 (14)0.0616 (16)0.0535 (17)0.0135 (12)0.0162 (12)0.0123 (13)
C300.0648 (17)0.0454 (13)0.0414 (16)0.0035 (12)0.0255 (12)0.0024 (11)
C310.0717 (17)0.0393 (12)0.0295 (13)0.0059 (11)0.0114 (12)0.0038 (10)
C320.0484 (13)0.0371 (12)0.0306 (13)0.0040 (10)0.0024 (10)0.0010 (10)
C330.0328 (11)0.0421 (12)0.0301 (12)0.0090 (9)0.0047 (9)0.0033 (9)
C340.0498 (14)0.0392 (12)0.0345 (13)0.0053 (10)0.0129 (10)0.0059 (10)
C350.0683 (17)0.0368 (13)0.0505 (17)0.0025 (11)0.0100 (13)0.0078 (11)
C360.0607 (17)0.0407 (13)0.0525 (17)0.0121 (12)0.0009 (13)0.0062 (12)
C370.0518 (16)0.0766 (19)0.0490 (17)0.0146 (14)0.0129 (13)0.0166 (15)
C380.0416 (14)0.0712 (17)0.0484 (16)0.0020 (12)0.0163 (11)0.0107 (13)
C410.0397 (12)0.0309 (10)0.0252 (12)0.0057 (9)0.0069 (9)0.0033 (9)
C420.0417 (13)0.0450 (13)0.0464 (15)0.0014 (10)0.0142 (11)0.0039 (11)
C430.0584 (16)0.0491 (14)0.0529 (17)0.0112 (12)0.0208 (13)0.0119 (12)
C440.0679 (17)0.0302 (11)0.0415 (15)0.0022 (11)0.0106 (12)0.0041 (10)
C450.0530 (14)0.0361 (12)0.0440 (15)0.0061 (10)0.0119 (11)0.0001 (10)
C460.0432 (13)0.0380 (12)0.0369 (14)0.0007 (9)0.0134 (10)0.0026 (10)
C470.0464 (13)0.0251 (10)0.0286 (12)0.0024 (9)0.0062 (9)0.0045 (8)
C480.0522 (14)0.0401 (12)0.0319 (13)0.0082 (10)0.0065 (10)0.0023 (10)
C490.0760 (18)0.0437 (13)0.0324 (14)0.0060 (12)0.0144 (12)0.0077 (11)
C500.0633 (16)0.0378 (12)0.0434 (15)0.0055 (11)0.0260 (12)0.0030 (11)
C510.0472 (14)0.0437 (13)0.0482 (16)0.0005 (10)0.0122 (11)0.0076 (11)
C520.0480 (13)0.0409 (12)0.0298 (13)0.0031 (10)0.0038 (10)0.0008 (10)
C530.0406 (12)0.0325 (11)0.0289 (12)0.0002 (9)0.0132 (9)0.0017 (9)
C540.0494 (14)0.0422 (12)0.0305 (13)0.0056 (10)0.0048 (10)0.0016 (10)
C550.0508 (15)0.0602 (15)0.0346 (14)0.0047 (12)0.0076 (11)0.0070 (12)
C560.0624 (17)0.0462 (14)0.0505 (17)0.0175 (12)0.0314 (13)0.0172 (12)
C570.0633 (17)0.0354 (12)0.0580 (18)0.0029 (11)0.0250 (14)0.0002 (12)
C580.0438 (13)0.0370 (12)0.0433 (14)0.0034 (9)0.0128 (10)0.0045 (10)
C610.0278 (10)0.0275 (10)0.0261 (11)0.0004 (8)0.0044 (8)0.0002 (8)
C620.0355 (12)0.0336 (11)0.0414 (14)0.0066 (9)0.0111 (10)0.0000 (10)
C630.0508 (14)0.0259 (10)0.0494 (15)0.0022 (9)0.0096 (11)0.0005 (10)
C640.0421 (13)0.0325 (11)0.0365 (13)0.0098 (9)0.0058 (10)0.0047 (9)
C650.0324 (11)0.0379 (11)0.0378 (13)0.0035 (9)0.0117 (9)0.0010 (10)
C660.0322 (11)0.0287 (10)0.0373 (13)0.0003 (8)0.0105 (9)0.0024 (9)
C670.0271 (10)0.0320 (10)0.0347 (13)0.0125 (8)0.0080 (9)0.0063 (9)
C680.0478 (14)0.0442 (13)0.0370 (14)0.0126 (10)0.0081 (11)0.0020 (11)
C690.0600 (16)0.0505 (15)0.0483 (16)0.0204 (12)0.0228 (13)0.0190 (12)
C700.0609 (17)0.0383 (13)0.073 (2)0.0163 (12)0.0333 (14)0.0227 (13)
C710.0496 (15)0.0369 (12)0.0589 (18)0.0010 (10)0.0169 (12)0.0068 (11)
C720.0367 (12)0.0334 (11)0.0415 (14)0.0042 (9)0.0066 (10)0.0067 (10)
C730.0310 (11)0.0272 (10)0.0354 (13)0.0050 (8)0.0119 (9)0.0016 (9)
C740.0375 (12)0.0326 (11)0.0474 (15)0.0009 (9)0.0178 (10)0.0028 (10)
C750.0576 (16)0.0386 (12)0.0536 (17)0.0100 (11)0.0293 (13)0.0134 (12)
C760.0682 (18)0.0510 (14)0.0335 (14)0.0275 (13)0.0163 (12)0.0060 (11)
C770.0488 (14)0.0452 (13)0.0382 (14)0.0150 (10)0.0031 (11)0.0084 (11)
C780.0339 (11)0.0346 (11)0.0340 (13)0.0031 (9)0.0081 (9)0.0028 (9)
P10.0250 (3)0.0309 (3)0.0311 (3)0.0030 (2)0.0056 (2)0.0015 (2)
P20.0341 (3)0.0471 (3)0.0290 (3)0.0004 (2)0.0025 (2)0.0025 (2)
P30.0415 (3)0.0350 (3)0.0287 (3)0.0001 (2)0.0051 (2)0.0011 (2)
P40.0244 (3)0.0340 (3)0.0345 (3)0.0030 (2)0.0055 (2)0.0011 (2)
Geometric parameters (Å, º) top
C1—C61.389 (3)C41—C461.392 (3)
C1—C21.398 (3)C41—C421.393 (3)
C1—P11.825 (2)C41—P31.834 (2)
C2—C31.373 (3)C42—C431.387 (4)
C3—C41.380 (4)C43—C441.378 (4)
C4—C51.378 (3)C44—C451.374 (4)
C5—C61.380 (3)C45—C461.385 (3)
C7—C81.396 (3)C47—C521.383 (3)
C7—C121.396 (3)C47—C481.392 (3)
C7—P11.8265 (19)C47—P31.835 (2)
C8—C91.381 (3)C48—C491.377 (3)
C9—C101.381 (3)C49—C501.371 (4)
C10—C111.381 (3)C50—C511.373 (3)
C11—C121.382 (3)C51—C521.382 (3)
C13—C141.388 (3)C53—C541.375 (3)
C13—C181.391 (3)C53—C581.393 (3)
C13—P11.836 (2)C53—P31.833 (2)
C14—C151.390 (3)C54—C551.384 (3)
C15—C161.373 (4)C55—C561.379 (4)
C16—C171.375 (3)C56—C571.368 (4)
C17—C181.377 (3)C57—C581.380 (3)
C21—C261.378 (3)C61—C661.387 (3)
C21—C221.388 (3)C61—C621.399 (3)
C21—P21.831 (2)C61—P41.8309 (19)
C22—C231.371 (4)C62—C631.378 (3)
C23—C241.362 (5)C63—C641.385 (3)
C24—C251.371 (4)C64—C651.374 (3)
C25—C261.391 (4)C65—C661.384 (3)
C27—C281.390 (3)C67—C681.384 (3)
C27—C321.391 (3)C67—C721.392 (3)
C27—P21.827 (2)C67—P41.837 (2)
C28—C291.373 (3)C68—C691.387 (4)
C29—C301.380 (4)C69—C701.376 (4)
C30—C311.368 (4)C70—C711.374 (4)
C31—C321.383 (3)C71—C721.383 (3)
C33—C341.386 (3)C73—C781.391 (3)
C33—C381.387 (3)C73—C741.394 (3)
C33—P21.825 (2)C73—P41.824 (2)
C34—C351.388 (3)C74—C751.376 (3)
C35—C361.370 (4)C75—C761.376 (4)
C36—C371.374 (4)C76—C771.376 (4)
C37—C381.376 (4)C77—C781.379 (3)
C6—C1—C2118.5 (2)C44—C45—C46120.7 (2)
C6—C1—P1123.67 (15)C45—C46—C41120.3 (2)
C2—C1—P1117.74 (16)C52—C47—C48117.9 (2)
C3—C2—C1120.7 (2)C52—C47—P3125.69 (16)
C2—C3—C4119.9 (2)C48—C47—P3116.42 (17)
C5—C4—C3120.2 (2)C49—C48—C47120.6 (2)
C4—C5—C6120.0 (2)C50—C49—C48120.6 (2)
C5—C6—C1120.6 (2)C49—C50—C51119.8 (2)
C8—C7—C12118.33 (17)C50—C51—C52119.7 (2)
C8—C7—P1117.59 (15)C51—C52—C47121.5 (2)
C12—C7—P1124.07 (15)C54—C53—C58118.53 (19)
C9—C8—C7120.6 (2)C54—C53—P3124.59 (16)
C10—C9—C8120.30 (19)C58—C53—P3116.87 (17)
C9—C10—C11119.79 (18)C53—C54—C55121.0 (2)
C10—C11—C12120.2 (2)C56—C55—C54119.8 (2)
C11—C12—C7120.69 (19)C57—C56—C55119.9 (2)
C14—C13—C18117.9 (2)C56—C57—C58120.4 (2)
C14—C13—P1124.65 (17)C57—C58—C53120.4 (2)
C18—C13—P1117.45 (15)C66—C61—C62118.57 (17)
C13—C14—C15120.7 (2)C66—C61—P4124.23 (15)
C16—C15—C14120.3 (2)C62—C61—P4117.19 (15)
C15—C16—C17119.6 (2)C63—C62—C61120.4 (2)
C16—C17—C18120.3 (2)C62—C63—C64120.2 (2)
C17—C18—C13121.2 (2)C65—C64—C63119.86 (19)
C26—C21—C22118.3 (2)C64—C65—C66120.3 (2)
C26—C21—P2124.76 (19)C65—C66—C61120.65 (19)
C22—C21—P2116.90 (18)C68—C67—C72118.1 (2)
C23—C22—C21121.7 (3)C68—C67—P4117.77 (17)
C24—C23—C22119.3 (3)C72—C67—P4124.12 (18)
C23—C24—C25120.6 (3)C67—C68—C69121.0 (2)
C24—C25—C26120.1 (3)C70—C69—C68120.1 (3)
C21—C26—C25120.0 (3)C71—C70—C69119.7 (2)
C28—C27—C32118.2 (2)C70—C71—C72120.3 (2)
C28—C27—P2124.96 (18)C71—C72—C67120.8 (2)
C32—C27—P2116.86 (16)C78—C73—C74118.3 (2)
C29—C28—C27121.0 (2)C78—C73—P4123.82 (16)
C28—C29—C30120.1 (2)C74—C73—P4117.84 (17)
C31—C30—C29119.9 (2)C75—C74—C73120.8 (2)
C30—C31—C32120.3 (2)C76—C75—C74120.1 (2)
C31—C32—C27120.6 (2)C75—C76—C77119.9 (2)
C34—C33—C38117.9 (2)C76—C77—C78120.3 (2)
C34—C33—P2124.94 (17)C77—C78—C73120.5 (2)
C38—C33—P2117.12 (19)C1—P1—C7102.22 (9)
C33—C34—C35120.9 (2)C1—P1—C13102.68 (9)
C36—C35—C34120.1 (3)C7—P1—C13102.38 (9)
C35—C36—C37119.8 (2)C33—P2—C27102.59 (10)
C36—C37—C38120.2 (2)C33—P2—C21102.28 (10)
C37—C38—C33121.2 (3)C27—P2—C21102.06 (10)
C46—C41—C42118.4 (2)C53—P3—C41102.58 (10)
C46—C41—P3124.74 (17)C53—P3—C47102.21 (10)
C42—C41—P3116.90 (16)C41—P3—C47102.49 (10)
C43—C42—C41120.8 (2)C73—P4—C61101.16 (9)
C44—C43—C42120.0 (2)C73—P4—C67101.95 (9)
C45—C44—C43119.8 (2)C61—P4—C67102.36 (9)
C6—C1—C2—C30.5 (3)C66—C61—C62—C631.8 (3)
P1—C1—C2—C3177.28 (16)P4—C61—C62—C63177.50 (17)
C1—C2—C3—C40.2 (3)C61—C62—C63—C641.3 (3)
C2—C3—C4—C50.8 (3)C62—C63—C64—C650.1 (3)
C3—C4—C5—C60.6 (3)C63—C64—C65—C660.5 (3)
C4—C5—C6—C10.1 (3)C64—C65—C66—C610.1 (3)
C2—C1—C6—C50.7 (3)C62—C61—C66—C651.2 (3)
P1—C1—C6—C5177.25 (16)P4—C61—C66—C65178.05 (16)
C12—C7—C8—C91.2 (3)C72—C67—C68—C691.5 (3)
P1—C7—C8—C9179.07 (17)P4—C67—C68—C69179.37 (17)
C7—C8—C9—C101.2 (3)C67—C68—C69—C702.0 (3)
C8—C9—C10—C110.3 (3)C68—C69—C70—C710.7 (4)
C9—C10—C11—C120.6 (3)C69—C70—C71—C720.9 (4)
C10—C11—C12—C70.5 (3)C70—C71—C72—C671.4 (3)
C8—C7—C12—C110.3 (3)C68—C67—C72—C710.2 (3)
P1—C7—C12—C11179.97 (16)P4—C67—C72—C71177.54 (16)
C18—C13—C14—C150.3 (3)C78—C73—C74—C750.2 (3)
P1—C13—C14—C15177.15 (16)P4—C73—C74—C75178.38 (17)
C13—C14—C15—C161.2 (3)C73—C74—C75—C760.2 (3)
C14—C15—C16—C171.1 (3)C74—C75—C76—C770.0 (4)
C15—C16—C17—C180.2 (3)C75—C76—C77—C780.2 (4)
C16—C17—C18—C130.6 (3)C76—C77—C78—C730.1 (3)
C14—C13—C18—C170.6 (3)C74—C73—C78—C770.1 (3)
P1—C13—C18—C17178.23 (16)P4—C73—C78—C77178.07 (16)
C26—C21—C22—C231.2 (4)C6—C1—P1—C79.21 (19)
P2—C21—C22—C23178.9 (2)C2—C1—P1—C7167.38 (16)
C21—C22—C23—C241.5 (4)C6—C1—P1—C1396.67 (18)
C22—C23—C24—C251.1 (4)C2—C1—P1—C1386.74 (17)
C23—C24—C25—C260.3 (5)C8—C7—P1—C183.83 (17)
C22—C21—C26—C250.3 (4)C12—C7—P1—C196.47 (19)
P2—C21—C26—C25177.9 (2)C8—C7—P1—C13170.05 (16)
C24—C25—C26—C210.1 (4)C12—C7—P1—C139.6 (2)
C32—C27—C28—C290.2 (3)C14—C13—P1—C11.42 (19)
P2—C27—C28—C29179.63 (19)C18—C13—P1—C1178.87 (15)
C27—C28—C29—C300.1 (4)C14—C13—P1—C7107.17 (17)
C28—C29—C30—C310.6 (4)C18—C13—P1—C775.37 (16)
C29—C30—C31—C320.9 (4)C34—C33—P2—C277.4 (2)
C30—C31—C32—C270.6 (3)C38—C33—P2—C27176.03 (19)
C28—C27—C32—C310.1 (3)C34—C33—P2—C21112.9 (2)
P2—C27—C32—C31179.93 (17)C38—C33—P2—C2170.5 (2)
C38—C33—C34—C350.7 (3)C28—C27—P2—C3380.0 (2)
P2—C33—C34—C35177.27 (18)C32—C27—P2—C33100.15 (18)
C33—C34—C35—C360.1 (4)C28—C27—P2—C2125.7 (2)
C34—C35—C36—C370.3 (4)C32—C27—P2—C21154.15 (17)
C35—C36—C37—C380.4 (4)C26—C21—P2—C3310.0 (2)
C36—C37—C38—C331.4 (4)C22—C21—P2—C33167.51 (17)
C34—C33—C38—C371.5 (4)C26—C21—P2—C2795.9 (2)
P2—C33—C38—C37178.3 (2)C22—C21—P2—C2786.56 (19)
C46—C41—C42—C430.5 (3)C54—C53—P3—C4124.7 (2)
P3—C41—C42—C43179.60 (19)C58—C53—P3—C41156.02 (18)
C41—C42—C43—C440.5 (4)C54—C53—P3—C4781.2 (2)
C42—C43—C44—C450.5 (4)C58—C53—P3—C4798.02 (19)
C43—C44—C45—C460.5 (4)C46—C41—P3—C5392.20 (19)
C44—C45—C46—C410.5 (3)C42—C41—P3—C5388.78 (18)
C42—C41—C46—C450.5 (3)C46—C41—P3—C4713.5 (2)
P3—C41—C46—C45179.51 (17)C42—C41—P3—C47165.47 (16)
C52—C47—C48—C490.7 (3)C52—C47—P3—C5319.3 (2)
P3—C47—C48—C49179.63 (18)C48—C47—P3—C53159.52 (17)
C47—C48—C49—C501.2 (4)C52—C47—P3—C4186.7 (2)
C48—C49—C50—C511.2 (4)C48—C47—P3—C4194.44 (18)
C49—C50—C51—C520.8 (4)C78—C73—P4—C619.4 (2)
C50—C51—C52—C470.3 (3)C74—C73—P4—C61168.67 (16)
C48—C47—C52—C510.3 (3)C78—C73—P4—C6796.00 (19)
P3—C47—C52—C51179.10 (17)C74—C73—P4—C6785.98 (17)
C58—C53—C54—C550.9 (4)C66—C61—P4—C7399.16 (19)
P3—C53—C54—C55178.34 (19)C62—C61—P4—C7380.15 (18)
C53—C54—C55—C560.3 (4)C66—C61—P4—C675.9 (2)
C54—C55—C56—C571.4 (4)C62—C61—P4—C67174.83 (17)
C55—C56—C57—C581.3 (4)C68—C67—P4—C73177.86 (16)
C56—C57—C58—C530.1 (4)C72—C67—P4—C730.14 (19)
C54—C53—C58—C571.0 (4)C68—C67—P4—C6177.72 (17)
P3—C53—C58—C57178.27 (19)C72—C67—P4—C61104.56 (17)
(II) Triphenylphosphinsulfide top
Crystal data top
C18H15PSZ = 4
Mr = 294.33F(000) = 616
Triclinic, P1Dx = 1.303 Mg m3
a = 9.542 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.207 (3) ÅCell parameters from 5000 reflections
c = 14.537 (4) Åθ = 2.5–25.0°
α = 88.89 (4)°µ = 0.31 mm1
β = 80.39 (4)°T = 180 K
γ = 78.28 (3)°Prism, yellow
V = 1500.5 (8) Å30.72 × 0.38 × 0.11 mm
Data collection top
Stoe IPDS
diffractometer
5111 independent reflections
Radiation source: fine-focus sealed X-ray tube4117 reflections with I > 2σ(I)
Planar graphite monochromatorRint = 0.050
Detector resolution: 6.667 pixels mm-1θmax = 25.2°, θmin = 2.2°
ϕ–oscill.,ϕ–incr.=1.5°,160 exposures scansh = 1111
Absorption correction: part of the refinement model (ΔF)
see _publ_section_exptl_prep
k = 1313
Tmin = 0.808, Tmax = 0.967l = 1717
13389 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079All H-atom parameters refined
S = 0.97Calculated w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
5111 reflections(Δ/σ)max = 0.044
481 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C18H15PSγ = 78.28 (3)°
Mr = 294.33V = 1500.5 (8) Å3
Triclinic, P1Z = 4
a = 9.542 (3) ÅMo Kα radiation
b = 11.207 (3) ŵ = 0.31 mm1
c = 14.537 (4) ÅT = 180 K
α = 88.89 (4)°0.72 × 0.38 × 0.11 mm
β = 80.39 (4)°
Data collection top
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 = 0.967Rint = 0.050
13389 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.079All H-atom parameters refined
S = 0.97Δρmax = 0.30 e Å3
5111 reflectionsΔρmin = 0.29 e Å3
481 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.22582 (16)0.62962 (14)0.31064 (11)0.0241 (3)
C20.36131 (18)0.55387 (16)0.31099 (13)0.0318 (4)
H20.421 (2)0.5759 (17)0.3497 (14)0.035 (5)*
C30.40196 (19)0.44911 (17)0.25548 (14)0.0384 (5)
H30.491 (2)0.3964 (19)0.2570 (15)0.047 (6)*
C40.3105 (2)0.41927 (16)0.20003 (15)0.0413 (5)
H40.337 (2)0.350 (2)0.1584 (17)0.054 (6)*
C50.1760 (2)0.49435 (16)0.19882 (15)0.0368 (4)
H50.117 (2)0.4772 (19)0.1616 (16)0.043 (6)*
C60.13372 (18)0.59902 (15)0.25490 (12)0.0300 (4)
H60.037 (2)0.6477 (18)0.2528 (14)0.042 (5)*
C70.15475 (16)0.89539 (14)0.30651 (11)0.0235 (3)
C80.17863 (17)0.88283 (15)0.20978 (12)0.0265 (4)
H80.1987 (19)0.8071 (17)0.1798 (13)0.027 (4)*
C90.17046 (18)0.98532 (16)0.15429 (13)0.0313 (4)
H90.185 (2)0.9766 (18)0.0909 (16)0.039 (5)*
C100.13903 (18)1.10039 (16)0.19458 (14)0.0329 (4)
H100.132 (2)1.1684 (18)0.1524 (14)0.038 (5)*
C110.1134 (2)1.11366 (16)0.29086 (14)0.0351 (4)
H110.091 (2)1.193 (2)0.3184 (17)0.060 (7)*
C120.1217 (2)1.01240 (16)0.34700 (13)0.0328 (4)
H120.106 (2)1.0197 (18)0.4115 (16)0.042 (5)*
C130.01018 (17)0.75894 (14)0.44168 (11)0.0238 (3)
C140.02360 (19)0.66488 (15)0.50483 (12)0.0304 (4)
H140.066 (2)0.6078 (18)0.5192 (14)0.039 (5)*
C150.1589 (2)0.65187 (16)0.54954 (13)0.0351 (4)
H150.170 (2)0.5912 (17)0.5932 (14)0.036 (5)*
C160.2812 (2)0.73277 (17)0.53178 (13)0.0365 (4)
H160.380 (2)0.7247 (19)0.5602 (16)0.050 (6)*
C170.26920 (19)0.82675 (17)0.47084 (13)0.0355 (4)
H170.356 (2)0.8862 (18)0.4599 (15)0.043 (5)*
C180.13345 (18)0.84070 (16)0.42495 (12)0.0299 (4)
H180.1261 (19)0.9063 (17)0.3819 (14)0.031 (5)*
C210.40168 (16)0.26181 (13)0.94533 (10)0.0200 (3)
C220.43122 (17)0.16715 (14)1.00764 (11)0.0255 (4)
H220.3673 (19)0.1072 (17)1.0173 (13)0.032 (5)*
C230.54799 (19)0.15737 (15)1.05378 (12)0.0303 (4)
H230.568 (2)0.0929 (18)1.0932 (14)0.036 (5)*
C240.6367 (2)0.24171 (16)1.03854 (13)0.0323 (4)
H240.717 (2)0.2389 (18)1.0669 (15)0.044 (6)*
C250.60755 (19)0.33573 (16)0.97767 (13)0.0315 (4)
H250.666 (2)0.3951 (19)0.9710 (15)0.041 (5)*
C260.49071 (17)0.34669 (14)0.93081 (11)0.0257 (4)
H260.4732 (19)0.4137 (17)0.8911 (14)0.031 (5)*
C270.30204 (15)0.13043 (13)0.81150 (11)0.0198 (3)
C280.44054 (17)0.10100 (15)0.75772 (12)0.0262 (4)
H280.5088 (18)0.1541 (15)0.7574 (12)0.025 (4)*
C290.47967 (19)0.00341 (16)0.70222 (13)0.0332 (4)
H290.575 (2)0.0222 (18)0.6620 (15)0.042 (5)*
C300.3827 (2)0.07899 (15)0.70013 (13)0.0351 (4)
H300.403 (2)0.1484 (19)0.6630 (15)0.041 (5)*
C310.2465 (2)0.05061 (15)0.75359 (14)0.0326 (4)
H310.179 (2)0.1044 (19)0.7527 (15)0.042 (5)*
C320.20583 (17)0.05352 (14)0.80951 (12)0.0255 (4)
H320.118 (2)0.0729 (15)0.8457 (13)0.026 (4)*
C330.23827 (15)0.39777 (13)0.81059 (11)0.0206 (3)
C340.27996 (17)0.38848 (14)0.71398 (11)0.0247 (3)
H340.3149 (19)0.3125 (17)0.6852 (13)0.029 (5)*
C350.26451 (19)0.49272 (15)0.66023 (12)0.0297 (4)
H350.295 (2)0.4845 (17)0.5950 (15)0.036 (5)*
C360.20754 (18)0.60609 (15)0.70206 (12)0.0291 (4)
H360.199 (2)0.6774 (18)0.6630 (14)0.039 (5)*
C370.16605 (17)0.61553 (14)0.79852 (12)0.0279 (4)
H370.1240 (19)0.6915 (17)0.8260 (13)0.032 (5)*
C380.18082 (17)0.51229 (14)0.85255 (12)0.0254 (3)
H380.1508 (18)0.5209 (15)0.9163 (14)0.027 (4)*
P10.17190 (4)0.76632 (4)0.38445 (3)0.02364 (11)
P210.24796 (4)0.26619 (3)0.88624 (3)0.01910 (10)
S10.30276 (5)0.77707 (5)0.47266 (3)0.04195 (14)
S210.06628 (4)0.27052 (4)0.97219 (3)0.03285 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0202 (7)0.0251 (7)0.0263 (8)0.0068 (6)0.0006 (7)0.0077 (6)
C20.0212 (8)0.0382 (9)0.0348 (10)0.0068 (7)0.0014 (8)0.0122 (8)
C30.0249 (9)0.0343 (9)0.0469 (11)0.0020 (8)0.0088 (8)0.0115 (8)
C40.0410 (11)0.0286 (9)0.0462 (11)0.0069 (8)0.0156 (10)0.0033 (8)
C50.0342 (10)0.0375 (10)0.0399 (10)0.0153 (8)0.0010 (9)0.0054 (8)
C60.0238 (8)0.0300 (8)0.0353 (10)0.0060 (7)0.0019 (7)0.0001 (7)
C70.0219 (7)0.0266 (8)0.0233 (8)0.0081 (6)0.0038 (6)0.0038 (6)
C80.0269 (8)0.0254 (8)0.0247 (8)0.0042 (7)0.0009 (7)0.0007 (7)
C90.0301 (8)0.0368 (9)0.0236 (9)0.0046 (7)0.0017 (7)0.0077 (7)
C100.0277 (8)0.0281 (8)0.0420 (10)0.0061 (7)0.0039 (8)0.0116 (8)
C110.0367 (9)0.0241 (8)0.0460 (11)0.0071 (7)0.0094 (8)0.0013 (8)
C120.0400 (10)0.0334 (9)0.0275 (9)0.0114 (7)0.0075 (8)0.0032 (7)
C130.0274 (8)0.0277 (8)0.0168 (7)0.0087 (6)0.0009 (6)0.0027 (6)
C140.0342 (9)0.0269 (8)0.0272 (9)0.0051 (7)0.0015 (7)0.0015 (7)
C150.0422 (10)0.0312 (9)0.0286 (9)0.0109 (8)0.0073 (8)0.0010 (7)
C160.0319 (9)0.0449 (10)0.0306 (10)0.0132 (8)0.0084 (8)0.0087 (8)
C170.0282 (9)0.0452 (10)0.0310 (9)0.0032 (8)0.0036 (7)0.0047 (8)
C180.0319 (9)0.0350 (9)0.0228 (8)0.0063 (7)0.0049 (7)0.0028 (7)
C210.0226 (7)0.0185 (7)0.0171 (7)0.0013 (6)0.0021 (6)0.0019 (6)
C220.0315 (8)0.0193 (7)0.0259 (8)0.0047 (6)0.0058 (7)0.0020 (6)
C230.0375 (9)0.0251 (8)0.0274 (9)0.0011 (7)0.0125 (7)0.0030 (7)
C240.0307 (9)0.0354 (9)0.0319 (9)0.0019 (7)0.0137 (8)0.0057 (7)
C250.0316 (9)0.0325 (9)0.0334 (9)0.0126 (7)0.0066 (8)0.0026 (7)
C260.0307 (8)0.0239 (8)0.0228 (8)0.0071 (7)0.0040 (7)0.0045 (7)
C270.0199 (7)0.0175 (7)0.0223 (7)0.0019 (6)0.0069 (6)0.0032 (6)
C280.0216 (8)0.0266 (8)0.0294 (9)0.0036 (6)0.0029 (7)0.0005 (7)
C290.0295 (9)0.0334 (9)0.0334 (9)0.0015 (7)0.0047 (8)0.0056 (7)
C300.0440 (10)0.0235 (8)0.0378 (10)0.0011 (7)0.0155 (9)0.0059 (7)
C310.0381 (9)0.0226 (8)0.0440 (10)0.0109 (7)0.0209 (9)0.0050 (7)
C320.0215 (8)0.0243 (8)0.0322 (9)0.0052 (6)0.0086 (7)0.0068 (7)
C330.0190 (7)0.0205 (7)0.0226 (8)0.0036 (6)0.0050 (6)0.0051 (6)
C340.0276 (8)0.0237 (8)0.0227 (8)0.0038 (6)0.0054 (7)0.0001 (6)
C350.0361 (9)0.0332 (9)0.0215 (9)0.0094 (7)0.0073 (7)0.0057 (7)
C360.0313 (8)0.0255 (8)0.0328 (9)0.0074 (7)0.0111 (7)0.0115 (7)
C370.0280 (8)0.0192 (8)0.0359 (9)0.0004 (6)0.0086 (7)0.0019 (7)
C380.0261 (8)0.0254 (8)0.0226 (8)0.0003 (6)0.0032 (7)0.0001 (6)
P10.0249 (2)0.0282 (2)0.0200 (2)0.00944 (16)0.00537 (16)0.00512 (16)
P210.01893 (19)0.01805 (18)0.0184 (2)0.00135 (14)0.00092 (15)0.00284 (14)
S10.0461 (3)0.0576 (3)0.0334 (3)0.0251 (2)0.0221 (2)0.0133 (2)
S210.0244 (2)0.0370 (2)0.0303 (2)0.00064 (17)0.00723 (17)0.00658 (18)
Geometric parameters (Å, º) top
C1—C61.385 (3)C21—C221.397 (2)
C1—C21.396 (2)C21—P211.8116 (17)
C1—P11.8226 (18)C22—C231.379 (3)
C2—C31.388 (3)C22—H220.99 (2)
C2—H20.93 (2)C23—C241.383 (3)
C3—C41.374 (3)C23—H230.92 (2)
C3—H30.94 (2)C24—C251.378 (3)
C4—C51.387 (3)C24—H240.93 (2)
C4—H40.96 (2)C25—C261.384 (3)
C5—C61.392 (3)C25—H250.95 (2)
C5—H50.89 (2)C26—H260.943 (19)
C6—H60.98 (2)C27—C321.385 (2)
C7—C81.392 (2)C27—C281.398 (2)
C7—C121.402 (2)C27—P211.8218 (17)
C7—P11.8181 (17)C28—C291.385 (2)
C8—C91.387 (2)C28—H280.967 (19)
C8—H80.931 (19)C29—C301.380 (3)
C9—C101.382 (3)C29—H290.98 (2)
C9—H90.91 (2)C30—C311.378 (3)
C10—C111.386 (3)C30—H300.92 (2)
C10—H100.97 (2)C31—C321.386 (3)
C11—C121.382 (3)C31—H310.97 (2)
C11—H110.95 (2)C32—H320.903 (18)
C12—H120.93 (2)C33—C341.394 (2)
C13—C181.390 (2)C33—C381.397 (2)
C13—C141.396 (2)C33—P211.8189 (16)
C13—P11.8139 (17)C34—C351.389 (2)
C14—C151.380 (2)C34—H340.929 (19)
C14—H141.01 (2)C35—C361.385 (3)
C15—C161.383 (3)C35—H350.95 (2)
C15—H150.93 (2)C36—C371.392 (3)
C16—C171.373 (3)C36—H360.97 (2)
C16—H160.99 (2)C37—C381.382 (2)
C17—C181.392 (3)C37—H370.931 (19)
C17—H170.98 (2)C38—H380.924 (19)
C18—H180.963 (19)P1—S11.9545 (9)
C21—C261.390 (2)P21—S211.9528 (9)
C6—C1—C2119.44 (16)C22—C23—C24119.96 (16)
C6—C1—P1120.99 (12)C22—C23—H23119.4 (13)
C2—C1—P1119.57 (15)C24—C23—H23120.6 (12)
C3—C2—C1119.6 (2)C25—C24—C23119.85 (18)
C3—C2—H2122.5 (11)C25—C24—H24116.5 (13)
C1—C2—H2117.8 (11)C23—C24—H24123.6 (13)
C4—C3—C2120.76 (17)C24—C25—C26120.83 (17)
C4—C3—H3119.1 (14)C24—C25—H25118.5 (13)
C2—C3—H3120.1 (14)C26—C25—H25120.6 (13)
C3—C4—C5120.03 (18)C25—C26—C21119.62 (15)
C3—C4—H4122.9 (14)C25—C26—H26118.0 (12)
C5—C4—H4117.0 (14)C21—C26—H26122.4 (11)
C4—C5—C6119.6 (2)C32—C27—C28119.37 (14)
C4—C5—H5120.8 (13)C32—C27—P21119.58 (12)
C6—C5—H5119.5 (13)C28—C27—P21121.03 (13)
C1—C6—C5120.52 (16)C29—C28—C27119.97 (17)
C1—C6—H6123.0 (12)C29—C28—H28119.4 (10)
C5—C6—H6116.4 (13)C27—C28—H28120.6 (10)
C8—C7—C12119.31 (15)C30—C29—C28120.24 (16)
C8—C7—P1123.14 (12)C30—C29—H29119.4 (12)
C12—C7—P1117.49 (13)C28—C29—H29120.3 (12)
C9—C8—C7120.12 (16)C31—C30—C29119.89 (16)
C9—C8—H8117.5 (11)C31—C30—H30116.5 (13)
C7—C8—H8122.4 (11)C29—C30—H30123.6 (13)
C10—C9—C8120.31 (17)C30—C31—C32120.51 (17)
C10—C9—H9119.9 (12)C30—C31—H31119.8 (12)
C8—C9—H9119.8 (13)C32—C31—H31119.7 (12)
C9—C10—C11119.89 (16)C27—C32—C31120.02 (15)
C9—C10—H10116.6 (12)C27—C32—H32118.2 (12)
C11—C10—H10123.5 (12)C31—C32—H32121.7 (12)
C12—C11—C10120.43 (17)C34—C33—C38119.52 (14)
C12—C11—H11119.9 (15)C34—C33—P21123.14 (12)
C10—C11—H11119.7 (15)C38—C33—P21117.30 (12)
C11—C12—C7119.93 (17)C35—C34—C33119.96 (15)
C11—C12—H12121.5 (13)C35—C34—H34119.8 (11)
C7—C12—H12118.6 (13)C33—C34—H34120.2 (11)
C18—C13—C14119.82 (15)C36—C35—C34120.36 (16)
C18—C13—P1123.30 (13)C36—C35—H35121.0 (11)
C14—C13—P1116.89 (12)C34—C35—H35118.6 (11)
C15—C14—C13120.19 (16)C35—C36—C37119.75 (15)
C15—C14—H14119.8 (11)C35—C36—H36118.6 (12)
C13—C14—H14120.0 (11)C37—C36—H36121.6 (12)
C14—C15—C16119.67 (17)C38—C37—C36120.29 (15)
C14—C15—H15121.2 (11)C38—C37—H37120.3 (11)
C16—C15—H15119.1 (11)C36—C37—H37119.3 (11)
C17—C16—C15120.65 (16)C37—C38—C33120.12 (15)
C17—C16—H16117.1 (12)C37—C38—H38118.6 (11)
C15—C16—H16122.3 (12)C33—C38—H38121.3 (11)
C16—C17—C18120.31 (17)C13—P1—C7106.83 (8)
C16—C17—H17120.9 (12)C13—P1—C1103.43 (8)
C18—C17—H17118.8 (12)C7—P1—C1106.60 (8)
C13—C18—C17119.36 (16)C13—P1—S1112.82 (6)
C13—C18—H18120.9 (10)C7—P1—S1112.47 (6)
C17—C18—H18119.8 (10)C1—P1—S1113.99 (6)
C26—C21—C22119.29 (15)C21—P21—C33107.11 (8)
C26—C21—P21123.21 (12)C21—P21—C27103.61 (7)
C22—C21—P21117.50 (12)C33—P21—C27107.38 (7)
C23—C22—C21120.44 (16)C21—P21—S21113.01 (5)
C23—C22—H22121.0 (11)C33—P21—S21111.97 (6)
C21—C22—H22118.6 (11)C27—P21—S21113.19 (6)
C6—C1—C2—C30.1 (2)C33—C34—C35—C360.1 (3)
P1—C1—C2—C3179.39 (12)C34—C35—C36—C370.2 (3)
C1—C2—C3—C40.1 (2)C35—C36—C37—C380.3 (3)
C2—C3—C4—C50.2 (3)C36—C37—C38—C330.3 (3)
C3—C4—C5—C60.8 (3)C34—C33—C38—C370.2 (2)
C2—C1—C6—C50.7 (2)P21—C33—C38—C37177.85 (13)
P1—C1—C6—C5179.96 (13)C18—C13—P1—C70.13 (17)
C4—C5—C6—C11.0 (3)C14—C13—P1—C7179.42 (13)
C12—C7—C8—C90.4 (2)C18—C13—P1—C1112.40 (15)
P1—C7—C8—C9176.89 (13)C14—C13—P1—C167.15 (14)
C7—C8—C9—C100.2 (3)C18—C13—P1—S1123.96 (14)
C8—C9—C10—C111.0 (3)C14—C13—P1—S156.49 (14)
C9—C10—C11—C121.2 (3)C8—C7—P1—C13109.31 (15)
C10—C11—C12—C70.6 (3)C12—C7—P1—C1373.39 (15)
C8—C7—C12—C110.1 (3)C8—C7—P1—C10.77 (16)
P1—C7—C12—C11177.27 (14)C12—C7—P1—C1176.52 (13)
C18—C13—C14—C151.0 (3)C8—C7—P1—S1126.39 (13)
P1—C13—C14—C15178.61 (14)C12—C7—P1—S150.91 (14)
C13—C14—C15—C160.3 (3)C6—C1—P1—C1347.09 (14)
C14—C15—C16—C170.7 (3)C2—C1—P1—C13132.20 (13)
C15—C16—C17—C181.0 (3)C6—C1—P1—C765.35 (14)
C14—C13—C18—C170.7 (3)C2—C1—P1—C7115.35 (13)
P1—C13—C18—C17178.85 (14)C6—C1—P1—S1169.95 (11)
C16—C17—C18—C130.3 (3)C2—C1—P1—S19.34 (14)
C26—C21—C22—C230.5 (2)C26—C21—P21—C330.41 (14)
P21—C21—C22—C23178.95 (12)C22—C21—P21—C33179.81 (11)
C21—C22—C23—C240.1 (2)C26—C21—P21—C27112.93 (13)
C22—C23—C24—C250.4 (3)C22—C21—P21—C2766.47 (13)
C23—C24—C25—C260.4 (3)C26—C21—P21—S21124.19 (12)
C24—C25—C26—C210.0 (2)C22—C21—P21—S2156.41 (12)
C22—C21—C26—C250.4 (2)C34—C33—P21—C21105.32 (15)
P21—C21—C26—C25178.95 (12)C38—C33—P21—C2177.16 (14)
C32—C27—C28—C290.8 (2)C34—C33—P21—C275.43 (16)
P21—C27—C28—C29179.29 (13)C38—C33—P21—C27172.09 (12)
C27—C28—C29—C300.3 (3)C34—C33—P21—S21130.26 (13)
C28—C29—C30—C310.1 (3)C38—C33—P21—S2147.26 (14)
C29—C30—C31—C320.1 (3)C32—C27—P21—C21132.71 (12)
C28—C27—C32—C310.9 (2)C28—C27—P21—C2145.74 (14)
P21—C27—C32—C31179.35 (12)C32—C27—P21—C33114.15 (13)
C30—C31—C32—C270.4 (2)C28—C27—P21—C3367.40 (14)
C38—C33—C34—C350.1 (2)C32—C27—P21—S219.95 (14)
P21—C33—C34—C35177.61 (13)C28—C27—P21—S21168.50 (11)

Experimental details

(I)(II)
Crystal data
Chemical formulaC18H15PC18H15PS
Mr262.27294.33
Crystal system, space groupTriclinic, P1Triclinic, P1
Temperature (K)180180
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)
V3)2866.0 (8)1500.5 (8)
Z84
Radiation typeMo KαMo Kα
µ (mm1)0.180.31
Crystal size (mm)0.48 × 0.48 × 0.280.72 × 0.38 × 0.11
Data collection
DiffractometerStoe IPDS
diffractometer
Stoe IPDS
diffractometer
Absorption correctionPart of the refinement model (ΔF)
see _publ_section_exptl_prep
Part of the refinement model (ΔF)
see _publ_section_exptl_prep
Tmin, Tmax0.921, 0.9530.808, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
17345, 9738, 6818 13389, 5111, 4117
Rint0.0320.050
(sin θ/λ)max1)0.6000.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.111, 0.92 0.029, 0.079, 0.97
No. of reflections97385111
No. of parameters685481
H-atom treatmentH-atom parameters constrainedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)1.02, 0.230.30, 0.29

Computer programs: IPDS2.87 (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XSTEP-2.18 (Stoe & Cie, 1997).

 

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