organic compounds
Tris[2-(deuteriomethylsulfanyl)phenyl]phosphine deuteriochloroform 0.125-solvate
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
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.
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2007); cell 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
10.1107/S1600536808010817/tk2251sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010817/tk2251Isup2.hkl
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.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 1.00 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). Scattering factors used for deuterium were those of hydrogen.The CDCl3 molecule was refined as a complete molecule of 1/8 occupancy about a site of symmetry, 3. The displacement factors of the three chloride atoms were restrained to be identical. The three C–Cl distances were restrained to within 0.01 Å of each other as were the Cl···Cl distances; the anisotropic temperature factors of the carbon atom were restrained to be nearly isotropic.
The final difference Fourier map had a peak 1 Å from P1 but was otherwise featureless.
Data collection: APEX2 (Bruker, 2007); cell
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).C21H12D9PS3·0.125CDCl3 | Dx = 1.458 Mg m−3 |
Mr = 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 |
Bruker SMART APEX diffractometer | 5929 independent reflections |
Radiation source: fine-focus sealed tube | 4200 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.089 |
ϕ and ω scans | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −29→29 |
Tmin = 0.925, Tmax = 1.000 | k = −29→30 |
36814 measured reflections | l = −30→32 |
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(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
5929 reflections | (Δ/σ)max = 0.001 |
329 parameters | Δρmax = 1.14 e Å−3 |
12 restraints | Δρmin = −0.49 e Å−3 |
C21H12D9PS3·0.125CDCl3 | Z = 24 |
Mr = 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 |
Bruker SMART APEX diffractometer | 5929 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4200 reflections with I > 2σ(I) |
Tmin = 0.925, Tmax = 1.000 | Rint = 0.089 |
36814 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 12 restraints |
wR(F2) = 0.194 | H-atom parameters constrained |
S = 1.18 | Δρmax = 1.14 e Å−3 |
5929 reflections | Δρmin = −0.49 e Å−3 |
329 parameters |
x | y | z | Uiso*/Ueq | 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 |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.925, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 36814, 5929, 4200 |
Rint | 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 |
Δρmax, Δρmin (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
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.