Triclinic polymorphs of tri­phenyl­phosphine and tri­phenyl­phosphine sulfide

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.

S1. Comment

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.

S2. Experimental

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

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

Crystal data

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) Å^3	0.48 × 0.48 × 0.28 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0683P)^2] where P = (Fo^2 + 2Fc^2)/3
9738 reflections	(Δ/σ)max = 0.004
685 parameters	Δρmax = 1.02 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

(II) Triphenylphosphinsulfide

Crystal data

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) Å^3	0.72 × 0.38 × 0.11 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	All H-atom parameters refined
S = 0.97	Calculated w = 1/[σ^2(Fo^2) + (0.050P)^2] where P = (Fo^2 + 2Fc^2)/3
5111 reflections	(Δ/σ)max = 0.044
481 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)