Tris[2-(deuteriomethyl­sulfan­yl)­phen­yl]­phosphine deuteriochloro­form 0.125-solvate

Wong, R.C.S.; Ooi, M.L.; Sakurai, H.; Ng, S.W.

doi:10.1107/S1600536808010817

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o898

doi:10.1107/S1600536808010817

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Tris[2-(deuteriomethylsulfanyl)phenyl]phosphine deuteriochloroform 0.125-solvate

Richard Chee Seng Wong,^a Mei Lee Ooi,^a Hidehiro Sakurai ^b and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bResearch Center for Molecular Nanoscience, Institute for Molecular Science, Myodaiji, Okazaki 444-8787, Japan
^*Correspondence e-mail: seikweng@um.edu.my

(Received 28 February 2008; accepted 18 April 2008; online 23 April 2008)

The title deuterated tripodal phosphine, C₂₁H₁₂D₉PS₃·0.125CDCl₃, crystallizes as two independent molecules, one of which lies on a general position and the other about a threefold rotation axis, and as a deuteriochloroform solvate. The solvent molecule is disordered about a site of symmetry 3, so that the ratio of phosphine to solvent is 8:1. The P atom adopts a pyramidal coordination geometry.

Related literature

For the synthesis and crystal structure of tris[(2-methylsulfanyl)phenyl]phosphine, see: Meek et al. (1976 ); Uttecht et al. (2005 ).

Experimental

Crystal data

C₂₁H₁₂D₉PS₃·0.125CDCl₃
M_r = 424.63
Hexagonal, $[R \overline 3]$
a = 23.090 (1) Å
c = 25.144 (1) Å
V = 11610 (1) Å³
Z = 24
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 100 (2) K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.925, T_max = 1.000 (expected range = 0.878–0.949)
36814 measured reflections
5929 independent reflections
4200 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.194
S = 1.18
5929 reflections
329 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 1.14 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010817/tk2251sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010817/tk2251Isup2.hkl

checkCIF report

Comment top

Tris[(2-methylsulfanyl)phenyl]phosphine is a tripodal ligand that yields a number of adducts with transition metals. The compound crystallizes without any solvent (Uttecht et al., 2005). We intended to synthesize the deuterated title compound to examine their coordination patterns. The present deuteriochloroform solvate (Scheme I, Fig. 1) is isostructural with the reported solvent-free compound, whose crystal structure has been described in detail. The deuterated chloroform molecule is disordered, and appears to occupy a only small portion of the unit cell. Its presence is not sufficient to cause much change in the unit cell volume.

Related literature top

For the synthesis and crystal structure of tris[(2-methylsulfanyl)phenyl]phosphine, see: Meek et al. (1976); Uttecht et al. (2005).

Experimental top

The procedure was adapted from a reported procedure (Meek et al., 1976). d₃-2-Bromothioanisole (2.50 g, 0.012 mol) was dissolved in dry ether (13 ml) at 273 K. To the solution was added over 2 h 1.6 M n-butyllithium in n-hexane (8 ml). A white precipitate separated after half the n-butyllithium was added. After the full quantity of the reagent was added, stirring was continued for another hour. Phosphorus trichloride (0.56 g, 0.004 mol) in ether (8 ml) was added over 3 h. The mixture was then allowed to warm up to room temperature before being hydrolyzed with 0.2 N hydrochloric acid (8 ml). The white solid was collected and washed with distilled water, ethanol and ether. The compound (1.216 g, 0.003 mol, 70% yield) was recrystallized from deuterated chloroform.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent (CD₃S-2-C₆H₄)₃P molecules showing atom labelling; the P2-molecule is located on a threefold axis of symmetry. Displacement ellipsoids are drawn at the 70% probability level. The disordered solvent molecule is omitted for clarity, and H and D atoms are shown as spheres of arbitrary radii.

Tris[2-(deuteriomethylsulfanyl)phenyl]phosphine deuteriochloroform 0.125-solvate top

Crystal data top

C₂₁H₁₂D₉PS₃·0.125CDCl₃	D_x = 1.458 Mg m⁻³
M_r = 424.63	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, R3	Cell parameters from 2990 reflections
Hall symbol: -R 3	θ = 2.6–21.9°
a = 23.090 (1) Å	µ = 0.52 mm⁻¹
c = 25.144 (1) Å	T = 100 K
V = 11610 (1) Å³	Diamondoid, colorless
Z = 24	0.20 × 0.15 × 0.10 mm
F(000) = 5214

Data collection top

Bruker SMART APEX diffractometer	5929 independent reflections
Radiation source: fine-focus sealed tube	4200 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→29
T_min = 0.925, T_max = 1.000	k = −29→30
36814 measured reflections	l = −30→32

Refinement top

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.194	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
5929 reflections	(Δ/σ)_max = 0.001
329 parameters	Δρ_max = 1.14 e Å⁻³
12 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₂₁H₁₂D₉PS₃·0.125CDCl₃	Z = 24
M_r = 424.63	Mo Kα radiation
Hexagonal, R3	µ = 0.52 mm⁻¹
a = 23.090 (1) Å	T = 100 K
c = 25.144 (1) Å	0.20 × 0.15 × 0.10 mm
V = 11610 (1) Å³

Data collection top

Bruker SMART APEX diffractometer	5929 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4200 reflections with I > 2σ(I)
T_min = 0.925, T_max = 1.000	R_int = 0.089
36814 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	12 restraints
wR(F²) = 0.194	H-atom parameters constrained
S = 1.18	Δρ_max = 1.14 e Å⁻³
5929 reflections	Δρ_min = −0.49 e Å⁻³
329 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.3613 (6)	0.7404 (8)	0.1620 (5)	0.0398 (13)	0.17
Cl2	0.2520 (7)	0.6046 (7)	0.1699 (7)	0.0398 (13)	0.17
Cl3	0.3839 (7)	0.6288 (7)	0.1538 (7)	0.0398 (13)	0.17
S1	0.23386 (5)	0.27581 (5)	0.07002 (4)	0.0297 (3)
S2	0.07625 (5)	0.35610 (5)	0.07921 (4)	0.0307 (3)
S3	0.22138 (5)	0.41664 (5)	−0.09462 (4)	0.0308 (3)
S4	0.03527 (5)	−0.10870 (5)	0.16513 (4)	0.0260 (2)
P1	0.21057 (5)	0.38934 (5)	0.02920 (4)	0.0231 (2)
P2	0.0000	0.0000	0.13345 (6)	0.0185 (3)
C1	0.29317 (18)	0.39837 (19)	0.02368 (14)	0.0241 (8)
C2	0.34626 (18)	0.45189 (19)	−0.00033 (15)	0.0268 (8)
H2	0.3415	0.4884	−0.0121	0.032*
C3	0.4062 (2)	0.4540 (2)	−0.00774 (15)	0.0302 (9)
H3	0.4417	0.4910	−0.0255	0.036*
C4	0.41479 (19)	0.4038 (2)	0.01014 (16)	0.0304 (9)
H4	0.4567	0.4062	0.0055	0.036*
C5	0.36333 (19)	0.3492 (2)	0.03509 (15)	0.0286 (9)
H5	0.3701	0.3143	0.0480	0.034*
C6	0.30210 (18)	0.34504 (18)	0.04128 (14)	0.0243 (8)
C7	0.2637 (2)	0.2188 (2)	0.07750 (18)	0.0359 (10)
H7A	0.2267	0.1749	0.0880	0.054*
H7B	0.2985	0.2353	0.1049	0.054*
H7C	0.2824	0.2147	0.0437	0.054*
C8	0.20467 (18)	0.39982 (18)	0.10092 (15)	0.0233 (8)
C9	0.2594 (2)	0.4248 (2)	0.13414 (16)	0.0347 (10)
H9	0.3029	0.4425	0.1194	0.042*
C10	0.2520 (2)	0.4246 (3)	0.18775 (17)	0.0403 (11)
H10	0.2904	0.4399	0.2098	0.048*
C11	0.1919 (3)	0.4032 (2)	0.21056 (17)	0.0413 (11)
H11	0.1881	0.4050	0.2481	0.050*
C12	0.1353 (2)	0.3784 (2)	0.17813 (16)	0.0316 (9)
H12	0.0922	0.3619	0.1934	0.038*
C13	0.14268 (19)	0.37816 (18)	0.12409 (16)	0.0257 (8)
C14	0.0046 (2)	0.3277 (2)	0.1209 (2)	0.0464 (13)
H14A	−0.0357	0.3098	0.0989	0.070*
H14B	0.0087	0.3652	0.1421	0.070*
H14C	0.0015	0.2926	0.1447	0.070*
C15	0.22337 (17)	0.46852 (18)	0.00343 (15)	0.0243 (8)
C16	0.22705 (18)	0.51897 (19)	0.03555 (16)	0.0279 (9)
H16	0.2279	0.5141	0.0730	0.034*
C17	0.2295 (2)	0.5742 (2)	0.01652 (17)	0.0376 (10)
H17	0.2304	0.6067	0.0402	0.045*
C18	0.2308 (2)	0.5838 (2)	−0.03719 (17)	0.0327 (9)
H18	0.2337	0.6235	−0.0509	0.039*
C19	0.22791 (19)	0.53560 (19)	−0.07160 (17)	0.0290 (9)
H19	0.2290	0.5422	−0.1090	0.035*
C20	0.22342 (17)	0.47825 (18)	−0.05158 (15)	0.0241 (8)
C21	0.1884 (2)	0.4301 (2)	−0.15450 (15)	0.0305 (9)
H21A	0.1774	0.3932	−0.1792	0.046*
H21B	0.2219	0.4723	−0.1708	0.046*
H21C	0.1480	0.4322	−0.1464	0.046*
C22	0.06906 (16)	−0.00245 (17)	0.10086 (14)	0.0181 (7)
C23	0.10721 (17)	0.04262 (17)	0.06167 (14)	0.0209 (7)
H23	0.0951	0.0739	0.0491	0.025*
C24	0.16278 (17)	0.04311 (17)	0.04031 (14)	0.0202 (7)
H24	0.1887	0.0748	0.0137	0.024*
C25	0.17988 (18)	−0.00197 (18)	0.05765 (14)	0.0225 (8)
H25	0.2178	−0.0020	0.0430	0.027*
C26	0.14256 (17)	−0.04786 (18)	0.09647 (14)	0.0223 (8)
H26	0.1550	−0.0792	0.1081	0.027*
C27	0.08693 (17)	−0.04882 (17)	0.11873 (14)	0.0204 (7)
C28	0.08728 (19)	−0.13719 (19)	0.19390 (15)	0.0273 (8)
H28A	0.0631	−0.1686	0.2228	0.041*
H28B	0.1280	−0.0989	0.2080	0.041*
H28C	0.0993	−0.1597	0.1667	0.041*
C29	0.3291 (7)	0.6581 (8)	0.1414 (7)	0.032 (5)	0.17
H29	0.3225	0.6570	0.1020	0.038*	0.17

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.055 (4)	0.037 (5)	0.028 (5)	0.024 (3)	0.006 (3)	0.003 (2)
Cl2	0.055 (4)	0.037 (5)	0.028 (5)	0.024 (3)	0.006 (3)	0.003 (2)
Cl3	0.055 (4)	0.037 (5)	0.028 (5)	0.024 (3)	0.006 (3)	0.003 (2)
S1	0.0303 (5)	0.0261 (5)	0.0302 (6)	0.0122 (4)	0.0060 (4)	0.0036 (4)
S2	0.0232 (5)	0.0291 (5)	0.0390 (6)	0.0125 (4)	−0.0012 (4)	−0.0026 (4)
S3	0.0447 (6)	0.0364 (6)	0.0198 (5)	0.0268 (5)	−0.0003 (4)	0.0004 (4)
S4	0.0226 (5)	0.0253 (5)	0.0301 (6)	0.0121 (4)	0.0043 (4)	0.0102 (4)
P1	0.0226 (5)	0.0268 (5)	0.0186 (5)	0.0114 (4)	0.0006 (4)	0.0006 (4)
P2	0.0195 (5)	0.0195 (5)	0.0166 (8)	0.0097 (2)	0.000	0.000
C1	0.0242 (19)	0.031 (2)	0.0183 (19)	0.0145 (16)	0.0002 (14)	−0.0035 (15)
C2	0.026 (2)	0.026 (2)	0.023 (2)	0.0084 (16)	−0.0042 (15)	−0.0034 (15)
C3	0.031 (2)	0.032 (2)	0.025 (2)	0.0142 (18)	0.0017 (17)	−0.0015 (17)
C4	0.0223 (19)	0.034 (2)	0.031 (2)	0.0114 (17)	−0.0014 (16)	−0.0081 (17)
C5	0.030 (2)	0.035 (2)	0.024 (2)	0.0191 (18)	0.0000 (16)	−0.0044 (16)
C6	0.028 (2)	0.0250 (19)	0.0163 (19)	0.0112 (16)	−0.0056 (15)	−0.0038 (15)
C7	0.036 (2)	0.029 (2)	0.041 (3)	0.0158 (19)	−0.0034 (19)	0.0022 (18)
C8	0.0282 (19)	0.0280 (19)	0.0192 (19)	0.0181 (17)	0.0027 (15)	0.0035 (15)
C9	0.029 (2)	0.055 (3)	0.026 (2)	0.025 (2)	−0.0013 (17)	−0.0074 (19)
C10	0.043 (3)	0.078 (3)	0.026 (2)	0.050 (3)	−0.0058 (19)	−0.003 (2)
C11	0.074 (3)	0.055 (3)	0.018 (2)	0.050 (3)	0.001 (2)	0.0003 (19)
C12	0.048 (2)	0.036 (2)	0.022 (2)	0.029 (2)	0.0137 (18)	0.0120 (17)
C13	0.031 (2)	0.0224 (19)	0.029 (2)	0.0171 (16)	0.0040 (16)	0.0039 (15)
C14	0.031 (2)	0.035 (2)	0.074 (4)	0.016 (2)	0.019 (2)	0.002 (2)
C15	0.0212 (18)	0.0258 (19)	0.027 (2)	0.0123 (16)	−0.0007 (15)	−0.0003 (15)
C16	0.030 (2)	0.029 (2)	0.020 (2)	0.0112 (17)	−0.0014 (16)	−0.0098 (16)
C17	0.043 (3)	0.033 (2)	0.033 (3)	0.017 (2)	0.000 (2)	−0.0094 (19)
C18	0.034 (2)	0.029 (2)	0.036 (2)	0.0163 (18)	−0.0002 (18)	0.0026 (18)
C19	0.030 (2)	0.033 (2)	0.025 (2)	0.0169 (18)	0.0003 (16)	0.0043 (17)
C20	0.0192 (18)	0.0257 (19)	0.027 (2)	0.0110 (15)	−0.0006 (15)	−0.0027 (16)
C21	0.035 (2)	0.038 (2)	0.022 (2)	0.0209 (19)	−0.0017 (17)	−0.0005 (17)
C22	0.0165 (16)	0.0204 (17)	0.0174 (18)	0.0092 (14)	−0.0027 (13)	−0.0026 (14)
C23	0.0232 (18)	0.0244 (18)	0.0173 (19)	0.0135 (15)	−0.0037 (14)	−0.0009 (14)
C24	0.0208 (17)	0.0188 (17)	0.0174 (18)	0.0072 (14)	0.0005 (14)	−0.0008 (14)
C25	0.0216 (18)	0.0274 (19)	0.0178 (19)	0.0117 (15)	0.0020 (14)	−0.0002 (15)
C26	0.0232 (18)	0.0216 (18)	0.023 (2)	0.0118 (15)	−0.0017 (15)	0.0010 (15)
C27	0.0187 (17)	0.0180 (17)	0.0198 (19)	0.0058 (14)	−0.0022 (14)	−0.0009 (14)
C28	0.032 (2)	0.031 (2)	0.024 (2)	0.0200 (18)	−0.0015 (16)	0.0055 (16)
C29	0.035 (8)	0.027 (9)	0.035 (7)	0.018 (7)	0.004 (10)	−0.018 (8)

Geometric parameters (Å, º) top

Cl1—C29	1.737 (9)	C10—H10	0.9500
Cl2—C29	1.736 (9)	C11—C12	1.398 (6)
Cl3—C29	1.736 (9)	C11—H11	0.9500
S1—C7	1.776 (4)	C12—C13	1.370 (5)
S1—C6	1.744 (4)	C12—H12	0.9500
S2—C14	1.783 (4)	C14—H14A	0.9800
S2—C13	1.762 (4)	C14—H14B	0.9800
S3—C21	1.783 (4)	C14—H14C	0.9800
S3—C20	1.769 (4)	C15—C16	1.385 (5)
S4—C27	1.745 (4)	C15—C20	1.401 (5)
S4—C28	1.786 (4)	C16—C17	1.337 (6)
P1—C1	1.817 (4)	C16—H16	0.9500
P1—C15	1.819 (4)	C17—C18	1.367 (6)
P1—C8	1.834 (4)	C17—H17	0.9500
P2—C22ⁱ	1.819 (3)	C18—C19	1.385 (6)
P2—C22	1.819 (3)	C18—H18	0.9500
P2—C22ⁱⁱ	1.819 (3)	C19—C20	1.371 (5)
C1—C2	1.371 (5)	C19—H19	0.9500
C1—C6	1.417 (5)	C21—H21A	0.9800
C2—C3	1.373 (5)	C21—H21B	0.9800
C2—H2	0.9500	C21—H21C	0.9800
C3—C4	1.346 (6)	C22—C23	1.383 (5)
C3—H3	0.9500	C22—C27	1.400 (5)
C4—C5	1.378 (5)	C23—C24	1.386 (5)
C4—H4	0.9500	C23—H23	0.9500
C5—C6	1.377 (5)	C24—C25	1.357 (5)
C5—H5	0.9500	C24—H24	0.9500
C7—H7A	0.9800	C25—C26	1.380 (5)
C7—H7B	0.9800	C25—H25	0.9500
C7—H7C	0.9800	C26—C27	1.391 (5)
C8—C13	1.387 (5)	C26—H26	0.9500
C8—C9	1.378 (5)	C28—H28A	0.9800
C9—C10	1.358 (6)	C28—H28B	0.9800
C9—H9	0.9500	C28—H28C	0.9800
C10—C11	1.347 (6)	C29—H29	1.0000

C7—S1—C6	102.45 (19)	H14A—C14—H14C	109.5
C14—S2—C13	104.0 (2)	H14B—C14—H14C	109.5
C21—S3—C20	102.65 (18)	C16—C15—C20	116.5 (3)
C27—S4—C28	104.09 (17)	C16—C15—P1	123.3 (3)
C1—P1—C15	102.93 (17)	C20—C15—P1	120.0 (3)
C1—P1—C8	101.70 (16)	C17—C16—C15	123.3 (4)
C15—P1—C8	101.72 (17)	C17—C16—H16	118.3
C22ⁱ—P2—C22	101.27 (14)	C15—C16—H16	118.3
C22ⁱ—P2—C22ⁱⁱ	101.27 (14)	C16—C17—C18	119.7 (4)
C22—P2—C22ⁱⁱ	101.27 (14)	C16—C17—H17	120.1
C2—C1—C6	117.9 (3)	C18—C17—H17	120.1
C2—C1—P1	123.4 (3)	C17—C18—C19	119.9 (4)
C6—C1—P1	118.5 (3)	C17—C18—H18	120.1
C3—C2—C1	121.5 (4)	C19—C18—H18	120.1
C3—C2—H2	119.2	C20—C19—C18	119.8 (4)
C1—C2—H2	119.2	C20—C19—H19	120.1
C4—C3—C2	120.3 (4)	C18—C19—H19	120.1
C4—C3—H3	119.9	C19—C20—C15	120.7 (4)
C2—C3—H3	119.9	C19—C20—S3	120.7 (3)
C3—C4—C5	120.6 (4)	C15—C20—S3	118.5 (3)
C3—C4—H4	119.7	S3—C21—H21A	109.5
C5—C4—H4	119.7	S3—C21—H21B	109.5
C4—C5—C6	120.0 (4)	H21A—C21—H21B	109.5
C4—C5—H5	120.0	S3—C21—H21C	109.5
C6—C5—H5	120.0	H21A—C21—H21C	109.5
C5—C6—C1	119.7 (4)	H21B—C21—H21C	109.5
C5—C6—S1	122.4 (3)	C23—C22—C27	118.9 (3)
C1—C6—S1	117.9 (3)	C23—C22—P2	122.4 (3)
S1—C7—H7A	109.5	C27—C22—P2	118.5 (3)
S1—C7—H7B	109.5	C24—C23—C22	121.4 (3)
H7A—C7—H7B	109.5	C24—C23—H23	119.3
S1—C7—H7C	109.5	C22—C23—H23	119.3
H7A—C7—H7C	109.5	C25—C24—C23	119.5 (3)
H7B—C7—H7C	109.5	C25—C24—H24	120.2
C13—C8—C9	117.5 (4)	C23—C24—H24	120.2
C13—C8—P1	119.8 (3)	C24—C25—C26	120.4 (3)
C9—C8—P1	122.6 (3)	C24—C25—H25	119.8
C10—C9—C8	120.8 (4)	C26—C25—H25	119.8
C10—C9—H9	119.6	C25—C26—C27	120.9 (3)
C8—C9—H9	119.6	C25—C26—H26	119.5
C11—C10—C9	121.9 (4)	C27—C26—H26	119.5
C11—C10—H10	119.0	C26—C27—C22	118.8 (3)
C9—C10—H10	119.0	C26—C27—S4	122.8 (3)
C10—C11—C12	118.9 (4)	C22—C27—S4	118.3 (3)
C10—C11—H11	120.5	S4—C28—H28A	109.5
C12—C11—H11	120.5	S4—C28—H28B	109.5
C11—C12—C13	119.2 (4)	H28A—C28—H28B	109.5
C11—C12—H12	120.4	S4—C28—H28C	109.5
C13—C12—H12	120.4	H28A—C28—H28C	109.5
C8—C13—C12	121.6 (4)	H28B—C28—H28C	109.5
C8—C13—S2	115.3 (3)	Cl1—C29—Cl3	112.2 (7)
C12—C13—S2	123.0 (3)	Cl1—C29—Cl2	112.4 (7)
S2—C14—H14A	109.5	Cl3—C29—Cl2	109.7 (7)
S2—C14—H14B	109.5	Cl1—C29—H29	107.5
H14A—C14—H14B	109.5	Cl3—C29—H29	107.5
S2—C14—H14C	109.5	Cl2—C29—H29	107.5

C15—P1—C1—C2	−6.0 (4)	C1—P1—C15—C16	−104.6 (3)
C8—P1—C1—C2	−111.1 (3)	C8—P1—C15—C16	0.5 (4)
C15—P1—C1—C6	179.1 (3)	C1—P1—C15—C20	81.7 (3)
C8—P1—C1—C6	74.0 (3)	C8—P1—C15—C20	−173.2 (3)
C6—C1—C2—C3	0.6 (6)	C20—C15—C16—C17	1.0 (6)
P1—C1—C2—C3	−174.3 (3)	P1—C15—C16—C17	−172.9 (3)
C1—C2—C3—C4	−2.1 (6)	C15—C16—C17—C18	−2.3 (6)
C2—C3—C4—C5	1.3 (6)	C16—C17—C18—C19	1.5 (6)
C3—C4—C5—C6	0.9 (6)	C17—C18—C19—C20	0.3 (6)
C4—C5—C6—C1	−2.4 (6)	C18—C19—C20—C15	−1.6 (6)
C4—C5—C6—S1	177.3 (3)	C18—C19—C20—S3	−178.7 (3)
C2—C1—C6—C5	1.6 (5)	C16—C15—C20—C19	0.9 (5)
P1—C1—C6—C5	176.7 (3)	P1—C15—C20—C19	175.0 (3)
C2—C1—C6—S1	−178.1 (3)	C16—C15—C20—S3	178.1 (3)
P1—C1—C6—S1	−3.0 (4)	P1—C15—C20—S3	−7.8 (4)
C7—S1—C6—C5	−7.1 (4)	C21—S3—C20—C19	−25.5 (4)
C7—S1—C6—C1	172.6 (3)	C21—S3—C20—C15	157.3 (3)
C1—P1—C8—C13	−161.9 (3)	C22ⁱ—P2—C22—C23	103.4 (2)
C15—P1—C8—C13	92.1 (3)	C22ⁱⁱ—P2—C22—C23	−0.7 (3)
C1—P1—C8—C9	13.9 (4)	C22ⁱ—P2—C22—C27	−81.1 (4)
C15—P1—C8—C9	−92.2 (4)	C22ⁱⁱ—P2—C22—C27	174.9 (3)
C13—C8—C9—C10	3.6 (6)	C27—C22—C23—C24	−0.6 (5)
P1—C8—C9—C10	−172.2 (3)	P2—C22—C23—C24	174.9 (3)
C8—C9—C10—C11	−3.3 (7)	C22—C23—C24—C25	0.8 (5)
C9—C10—C11—C12	2.3 (7)	C23—C24—C25—C26	−0.3 (5)
C10—C11—C12—C13	−1.7 (6)	C24—C25—C26—C27	−0.2 (5)
C9—C8—C13—C12	−3.1 (6)	C25—C26—C27—C22	0.3 (5)
P1—C8—C13—C12	172.8 (3)	C25—C26—C27—S4	176.2 (3)
C9—C8—C13—S2	172.8 (3)	C23—C22—C27—C26	0.1 (5)
P1—C8—C13—S2	−11.3 (4)	P2—C22—C27—C26	−175.6 (3)
C11—C12—C13—C8	2.2 (6)	C23—C22—C27—S4	−176.0 (3)
C11—C12—C13—S2	−173.4 (3)	P2—C22—C27—S4	8.3 (4)
C14—S2—C13—C8	177.7 (3)	C28—S4—C27—C26	23.3 (4)
C14—S2—C13—C12	−6.5 (4)	C28—S4—C27—C22	−160.7 (3)

Symmetry codes: (i) −x+y, −x, z; (ii) −y, x−y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₂D₉PS₃·0.125CDCl₃
M_r	424.63
Crystal system, space group	Hexagonal, R3
Temperature (K)	100
a, c (Å)	23.090 (1), 25.144 (1)
V (Å³)	11610 (1)
Z	24
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.925, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	36814, 5929, 4200
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.194, 1.18
No. of reflections	5929
No. of parameters	329
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.14, −0.49

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Acknowledgements

We thank the ScienceFund MOSTI (03-01-03-SF0209) for funding the study, and the University of Malaya for the purchase of the diffractometer.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Meek, D. W., Dyer, G. & Workman, M. O. (1976). Inorg. Synth. 16, 168–174. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Uttecht, J.-G., Tuczek, F. & Näther, C. (2005). Acta Cryst. E61, o2916–o2917. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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