organic compounds
(2-{[2-(diphenylphosphino)phenyl]thio}phenyl)diphenylphosphine sulfide
aServicio Difracción Rayos X, Universidad Autónoma de Barcelona, 08193 Cerdanyola, Spain, and bDepartamento Química, Universidad Autónoma de Barcelona, 08193 Cerdanyola, Spain
*Correspondence e-mail: angel.alvarez@uab.es
In the title compound, C36H28P2S2, the dihedral angle between the central benzene rings is 66.95 (13)°. In the crystal, molecules are linked via Car—H⋯π and π–π interactions [shortest centroid–centroid distance between benzene rings = 3.897 (2) Å].
Related literature
For related structures, see: Deb & Dutta (2010); Deb et al. (2010); Tooke et al. (2005); Pintado-Alba et al. (2004). For additional information on hemilabile ligands, see: Dallanegra et al. (2012); Marimuthu et al. (2012); Tello-López (2010).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812041347/pk2445sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041347/pk2445Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812041347/pk2445Isup3.cml
Bis-[2-(diphenylphosphino)phenyl]sulfane (1.0 g, 1.8 mmol) (obtained as described by Tello-López, 2010), sulfur (58 mg, 1.8 mmol), and CH2Cl2 (50 ml) were placed in a 50 ml Schlenk flask. The mixture was stirred under nitrogen at room temperature for 48 h. The solution was evaporated to dryness and the solid was purified by silica gel δ 43.1(s), -11.2(s) p.p.m. IR (KBr): 3052–2921, 1583–1477, 1434, 1100, 747, 692, 518 cm-1. Single crystals were obtained by evaporation of a toluene solution.
(CH2Cl2/Hexane 3:1) and by crystallization from CH2Cl2/MeOH 1:3 to yield the title product (0.34 g, 32%). 31P{1H} NMR (101 MHz, CDCl3 298 K):H atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å and with Uiso(H) = 1.2 times Ueq(C).
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. Examples of hemilabile ligands. | |
Fig. 2. Molecular structure of the title compound with anisotropic displacement ellipsoids at the 50% probability level. |
C36H28P2S2 | Z = 2 |
Mr = 586.64 | F(000) = 612 |
Triclinic, P1 | Dx = 1.288 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8595 (10) Å | Cell parameters from 1777 reflections |
b = 11.0267 (10) Å | θ = 2.6–23.0° |
c = 13.3031 (12) Å | µ = 0.31 mm−1 |
α = 76.404 (2)° | T = 296 K |
β = 79.151 (2)° | Prism, colourless |
γ = 81.976 (2)° | 0.34 × 0.22 × 0.20 mm |
V = 1513.1 (2) Å3 |
Bruker SMART APEX diffractometer | 6991 independent reflections |
Radiation source: fine-focus sealed tube | 4414 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.13 pixels mm-1 | θmax = 28.9°, θmin = 1.6° |
ϕ and ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | k = −8→14 |
Tmin = 0.806, Tmax = 0.941 | l = −17→17 |
10362 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters not refined |
S = 0.98 | w = 1/[σ2(Fo2) + (0.059P)2] where P = (Fo2 + 2Fc2)/3 |
6991 reflections | (Δ/σ)max < 0.001 |
361 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C36H28P2S2 | γ = 81.976 (2)° |
Mr = 586.64 | V = 1513.1 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.8595 (10) Å | Mo Kα radiation |
b = 11.0267 (10) Å | µ = 0.31 mm−1 |
c = 13.3031 (12) Å | T = 296 K |
α = 76.404 (2)° | 0.34 × 0.22 × 0.20 mm |
β = 79.151 (2)° |
Bruker SMART APEX diffractometer | 6991 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 4414 reflections with I > 2σ(I) |
Tmin = 0.806, Tmax = 0.941 | Rint = 0.029 |
10362 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters not refined |
S = 0.98 | Δρmax = 0.46 e Å−3 |
6991 reflections | Δρmin = −0.29 e Å−3 |
361 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C41 | 0.4459 (2) | 0.2347 (2) | 0.3240 (2) | 0.0322 (6) | |
C42 | 0.3286 (3) | 0.2950 (2) | 0.3009 (2) | 0.0337 (6) | |
C43 | 0.2504 (3) | 0.2351 (3) | 0.2616 (2) | 0.0421 (7) | |
H43 | 0.1724 | 0.2752 | 0.2473 | 0.050* | |
C44 | 0.2877 (3) | 0.1157 (3) | 0.2436 (2) | 0.0452 (7) | |
H44 | 0.2343 | 0.0758 | 0.2179 | 0.054* | |
C45 | 0.4029 (3) | 0.0558 (3) | 0.2634 (2) | 0.0466 (8) | |
H45 | 0.4281 | −0.0240 | 0.2506 | 0.056* | |
C46 | 0.4811 (3) | 0.1158 (3) | 0.3026 (2) | 0.0426 (7) | |
H46 | 0.5596 | 0.0754 | 0.3150 | 0.051* | |
C51 | 0.4753 (2) | 0.2811 (3) | 0.5186 (2) | 0.0361 (6) | |
C52 | 0.5194 (3) | 0.3387 (3) | 0.5850 (2) | 0.0468 (7) | |
H52 | 0.5817 | 0.3929 | 0.5580 | 0.056* | |
C53 | 0.4717 (3) | 0.3165 (3) | 0.6914 (3) | 0.0547 (9) | |
H53 | 0.5032 | 0.3543 | 0.7355 | 0.066* | |
C54 | 0.3779 (3) | 0.2387 (3) | 0.7314 (2) | 0.0543 (9) | |
H54 | 0.3461 | 0.2233 | 0.8027 | 0.065* | |
C55 | 0.3308 (3) | 0.1834 (3) | 0.6661 (2) | 0.0507 (8) | |
H55 | 0.2659 | 0.1322 | 0.6929 | 0.061* | |
C56 | 0.3800 (3) | 0.2038 (3) | 0.5604 (2) | 0.0423 (7) | |
H56 | 0.3486 | 0.1651 | 0.5169 | 0.051* | |
C61 | 0.6912 (2) | 0.2077 (3) | 0.3795 (2) | 0.0382 (7) | |
C62 | 0.7832 (3) | 0.2262 (3) | 0.2904 (2) | 0.0507 (8) | |
H62 | 0.7688 | 0.2910 | 0.2337 | 0.061* | |
C63 | 0.8948 (3) | 0.1504 (4) | 0.2849 (3) | 0.0626 (10) | |
H63 | 0.9544 | 0.1632 | 0.2243 | 0.075* | |
C64 | 0.9187 (3) | 0.0555 (4) | 0.3690 (3) | 0.0650 (11) | |
H64 | 0.9944 | 0.0042 | 0.3654 | 0.078* | |
C65 | 0.8313 (3) | 0.0372 (3) | 0.4570 (3) | 0.0601 (9) | |
H65 | 0.8479 | −0.0264 | 0.5140 | 0.072* | |
C66 | 0.7179 (3) | 0.1118 (3) | 0.4634 (2) | 0.0479 (8) | |
H66 | 0.6590 | 0.0977 | 0.5244 | 0.057* | |
C11 | 0.0501 (2) | 0.5606 (2) | 0.2821 (2) | 0.0330 (6) | |
C12 | 0.1193 (2) | 0.4622 (2) | 0.3423 (2) | 0.0330 (6) | |
C13 | 0.0563 (3) | 0.3762 (3) | 0.4220 (2) | 0.0423 (7) | |
H13 | 0.1023 | 0.3118 | 0.4623 | 0.051* | |
C14 | −0.0737 (3) | 0.3851 (3) | 0.4424 (2) | 0.0474 (8) | |
H14 | −0.1148 | 0.3265 | 0.4957 | 0.057* | |
C15 | −0.1419 (3) | 0.4801 (3) | 0.3838 (2) | 0.0506 (8) | |
H15 | −0.2295 | 0.4859 | 0.3970 | 0.061* | |
C16 | −0.0809 (3) | 0.5676 (3) | 0.3054 (2) | 0.0429 (7) | |
H16 | −0.1284 | 0.6327 | 0.2671 | 0.051* | |
C21 | 0.2330 (3) | 0.6318 (3) | 0.0877 (2) | 0.0423 (7) | |
C22 | 0.3334 (3) | 0.7007 (3) | 0.0351 (3) | 0.0560 (9) | |
H22 | 0.3477 | 0.7705 | 0.0576 | 0.067* | |
C23 | 0.4119 (3) | 0.6655 (4) | −0.0504 (3) | 0.0701 (11) | |
H23 | 0.4779 | 0.7125 | −0.0856 | 0.084* | |
C24 | 0.3926 (4) | 0.5619 (4) | −0.0831 (3) | 0.0733 (12) | |
H24 | 0.4457 | 0.5386 | −0.1404 | 0.088* | |
C25 | 0.2949 (4) | 0.4923 (4) | −0.0316 (3) | 0.0667 (10) | |
H25 | 0.2823 | 0.4217 | −0.0538 | 0.080* | |
C26 | 0.2147 (3) | 0.5276 (3) | 0.0538 (2) | 0.0540 (9) | |
H26 | 0.1484 | 0.4806 | 0.0882 | 0.065* | |
C31 | −0.0005 (3) | 0.7811 (3) | 0.1210 (2) | 0.0383 (7) | |
C32 | −0.0465 (3) | 0.7388 (3) | 0.0465 (2) | 0.0541 (8) | |
H32 | −0.0143 | 0.6609 | 0.0321 | 0.065* | |
C33 | −0.1383 (3) | 0.8088 (3) | −0.0065 (3) | 0.0614 (10) | |
H33 | −0.1678 | 0.7785 | −0.0561 | 0.074* | |
C34 | −0.1865 (3) | 0.9242 (3) | 0.0142 (3) | 0.0579 (9) | |
H34 | −0.2482 | 0.9723 | −0.0221 | 0.070* | |
C35 | −0.1440 (3) | 0.9685 (3) | 0.0880 (3) | 0.0552 (9) | |
H35 | −0.1771 | 1.0461 | 0.1024 | 0.066* | |
C36 | −0.0508 (3) | 0.8964 (3) | 0.1412 (2) | 0.0448 (7) | |
H36 | −0.0220 | 0.9266 | 0.1913 | 0.054* | |
P1 | 0.12398 (7) | 0.69086 (7) | 0.19072 (6) | 0.03650 (19) | |
P2 | 0.54595 (7) | 0.31492 (7) | 0.37954 (6) | 0.03589 (19) | |
S1 | 0.19859 (8) | 0.79139 (8) | 0.26148 (7) | 0.0525 (2) | |
S2 | 0.28748 (7) | 0.45079 (7) | 0.32212 (6) | 0.03975 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C41 | 0.0324 (14) | 0.0306 (14) | 0.0319 (14) | 0.0022 (11) | −0.0072 (11) | −0.0047 (12) |
C42 | 0.0402 (15) | 0.0285 (14) | 0.0313 (14) | 0.0029 (12) | −0.0089 (12) | −0.0055 (12) |
C43 | 0.0443 (17) | 0.0390 (17) | 0.0448 (17) | 0.0046 (14) | −0.0201 (14) | −0.0077 (14) |
C44 | 0.0531 (19) | 0.0401 (17) | 0.0475 (17) | −0.0036 (14) | −0.0196 (15) | −0.0107 (15) |
C45 | 0.058 (2) | 0.0345 (16) | 0.0486 (18) | 0.0053 (15) | −0.0144 (15) | −0.0131 (15) |
C46 | 0.0408 (17) | 0.0408 (17) | 0.0448 (17) | 0.0091 (13) | −0.0115 (14) | −0.0105 (14) |
C51 | 0.0328 (15) | 0.0362 (15) | 0.0379 (15) | 0.0059 (12) | −0.0083 (12) | −0.0083 (13) |
C52 | 0.0452 (18) | 0.0511 (19) | 0.0460 (18) | −0.0071 (15) | −0.0071 (14) | −0.0131 (16) |
C53 | 0.062 (2) | 0.061 (2) | 0.0471 (19) | −0.0007 (18) | −0.0130 (17) | −0.0214 (18) |
C54 | 0.056 (2) | 0.059 (2) | 0.0393 (17) | 0.0110 (17) | 0.0005 (16) | −0.0110 (17) |
C55 | 0.0415 (18) | 0.051 (2) | 0.0509 (19) | −0.0021 (15) | 0.0034 (15) | −0.0045 (16) |
C56 | 0.0410 (17) | 0.0403 (17) | 0.0439 (17) | −0.0020 (13) | −0.0065 (14) | −0.0069 (14) |
C61 | 0.0321 (15) | 0.0417 (17) | 0.0422 (16) | −0.0028 (13) | −0.0077 (13) | −0.0108 (14) |
C62 | 0.0440 (18) | 0.061 (2) | 0.0461 (18) | −0.0004 (16) | −0.0088 (15) | −0.0119 (17) |
C63 | 0.0427 (19) | 0.088 (3) | 0.062 (2) | 0.0040 (19) | −0.0042 (17) | −0.034 (2) |
C64 | 0.043 (2) | 0.083 (3) | 0.079 (3) | 0.0206 (19) | −0.0251 (19) | −0.041 (2) |
C65 | 0.056 (2) | 0.060 (2) | 0.067 (2) | 0.0154 (18) | −0.0290 (19) | −0.0149 (19) |
C66 | 0.0417 (17) | 0.0490 (19) | 0.0471 (18) | 0.0038 (15) | −0.0081 (14) | −0.0028 (16) |
C11 | 0.0327 (14) | 0.0326 (15) | 0.0331 (14) | −0.0001 (12) | −0.0066 (12) | −0.0069 (12) |
C12 | 0.0338 (14) | 0.0332 (15) | 0.0328 (14) | 0.0000 (12) | −0.0077 (12) | −0.0088 (12) |
C13 | 0.0536 (19) | 0.0327 (16) | 0.0380 (16) | −0.0019 (14) | −0.0106 (14) | −0.0015 (13) |
C14 | 0.055 (2) | 0.0422 (18) | 0.0417 (17) | −0.0144 (15) | 0.0027 (15) | −0.0047 (15) |
C15 | 0.0382 (17) | 0.0511 (19) | 0.057 (2) | −0.0060 (15) | 0.0022 (15) | −0.0084 (17) |
C16 | 0.0370 (16) | 0.0411 (17) | 0.0465 (17) | 0.0038 (13) | −0.0078 (13) | −0.0051 (15) |
C21 | 0.0421 (17) | 0.0389 (17) | 0.0392 (16) | 0.0046 (13) | −0.0072 (13) | 0.0003 (14) |
C22 | 0.0467 (19) | 0.056 (2) | 0.053 (2) | −0.0013 (16) | −0.0026 (16) | 0.0043 (17) |
C23 | 0.054 (2) | 0.080 (3) | 0.051 (2) | 0.006 (2) | 0.0097 (17) | 0.015 (2) |
C24 | 0.076 (3) | 0.078 (3) | 0.045 (2) | 0.024 (2) | 0.0067 (19) | −0.003 (2) |
C25 | 0.083 (3) | 0.062 (2) | 0.049 (2) | 0.014 (2) | −0.004 (2) | −0.0173 (19) |
C26 | 0.058 (2) | 0.050 (2) | 0.0473 (19) | 0.0020 (16) | −0.0004 (16) | −0.0087 (17) |
C31 | 0.0409 (16) | 0.0348 (16) | 0.0342 (15) | 0.0020 (13) | −0.0061 (13) | −0.0010 (13) |
C32 | 0.062 (2) | 0.0462 (19) | 0.0534 (19) | 0.0093 (16) | −0.0195 (17) | −0.0096 (17) |
C33 | 0.069 (2) | 0.066 (2) | 0.050 (2) | 0.0031 (19) | −0.0292 (18) | −0.0048 (18) |
C34 | 0.053 (2) | 0.060 (2) | 0.050 (2) | 0.0073 (17) | −0.0192 (16) | 0.0099 (18) |
C35 | 0.051 (2) | 0.0460 (19) | 0.056 (2) | 0.0128 (16) | −0.0047 (16) | −0.0009 (17) |
C36 | 0.0499 (18) | 0.0389 (17) | 0.0403 (16) | 0.0025 (14) | −0.0054 (14) | −0.0038 (14) |
P1 | 0.0373 (4) | 0.0316 (4) | 0.0373 (4) | 0.0013 (3) | −0.0079 (3) | −0.0023 (3) |
P2 | 0.0335 (4) | 0.0352 (4) | 0.0375 (4) | −0.0007 (3) | −0.0076 (3) | −0.0052 (3) |
S1 | 0.0574 (5) | 0.0426 (5) | 0.0608 (5) | −0.0065 (4) | −0.0208 (4) | −0.0079 (4) |
S2 | 0.0366 (4) | 0.0311 (4) | 0.0525 (4) | 0.0034 (3) | −0.0158 (3) | −0.0080 (3) |
C41—C46 | 1.394 (4) | C11—C12 | 1.405 (4) |
C41—C42 | 1.405 (3) | C11—P1 | 1.822 (3) |
C41—P2 | 1.840 (3) | C12—C13 | 1.388 (4) |
C42—C43 | 1.385 (4) | C12—S2 | 1.786 (3) |
C42—S2 | 1.788 (3) | C13—C14 | 1.381 (4) |
C43—C44 | 1.384 (4) | C13—H13 | 0.9300 |
C43—H43 | 0.9300 | C14—C15 | 1.368 (4) |
C44—C45 | 1.372 (4) | C14—H14 | 0.9300 |
C44—H44 | 0.9300 | C15—C16 | 1.380 (4) |
C45—C46 | 1.384 (4) | C15—H15 | 0.9300 |
C45—H45 | 0.9300 | C16—H16 | 0.9300 |
C46—H46 | 0.9300 | C21—C26 | 1.381 (4) |
C51—C56 | 1.383 (4) | C21—C22 | 1.397 (4) |
C51—C52 | 1.386 (4) | C21—P1 | 1.815 (3) |
C51—P2 | 1.836 (3) | C22—C23 | 1.385 (5) |
C52—C53 | 1.388 (4) | C22—H22 | 0.9300 |
C52—H52 | 0.9300 | C23—C24 | 1.369 (5) |
C53—C54 | 1.372 (4) | C23—H23 | 0.9300 |
C53—H53 | 0.9300 | C24—C25 | 1.375 (5) |
C54—C55 | 1.375 (4) | C24—H24 | 0.9300 |
C54—H54 | 0.9300 | C25—C26 | 1.393 (4) |
C55—C56 | 1.383 (4) | C25—H25 | 0.9300 |
C55—H55 | 0.9300 | C26—H26 | 0.9300 |
C56—H56 | 0.9300 | C31—C36 | 1.379 (4) |
C61—C66 | 1.389 (4) | C31—C32 | 1.384 (4) |
C61—C62 | 1.393 (4) | C31—P1 | 1.828 (3) |
C61—P2 | 1.834 (3) | C32—C33 | 1.371 (4) |
C62—C63 | 1.373 (4) | C32—H32 | 0.9300 |
C62—H62 | 0.9300 | C33—C34 | 1.376 (4) |
C63—C64 | 1.377 (5) | C33—H33 | 0.9300 |
C63—H63 | 0.9300 | C34—C35 | 1.369 (4) |
C64—C65 | 1.356 (5) | C34—H34 | 0.9300 |
C64—H64 | 0.9300 | C35—C36 | 1.392 (4) |
C65—C66 | 1.383 (4) | C35—H35 | 0.9300 |
C65—H65 | 0.9300 | C36—H36 | 0.9300 |
C66—H66 | 0.9300 | P1—S1 | 1.9494 (11) |
C11—C16 | 1.393 (4) | ||
S1···S2 | 3.6803 (12) | S2···P2 | 3.1308 (11) |
C46—C41—C42 | 117.6 (2) | C11—C12—S2 | 120.9 (2) |
C46—C41—P2 | 123.1 (2) | C14—C13—C12 | 120.9 (3) |
C42—C41—P2 | 119.37 (19) | C14—C13—H13 | 119.5 |
C43—C42—C41 | 120.3 (2) | C12—C13—H13 | 119.5 |
C43—C42—S2 | 122.3 (2) | C15—C14—C13 | 119.8 (3) |
C41—C42—S2 | 117.4 (2) | C15—C14—H14 | 120.1 |
C44—C43—C42 | 120.3 (3) | C13—C14—H14 | 120.1 |
C44—C43—H43 | 119.9 | C14—C15—C16 | 120.1 (3) |
C42—C43—H43 | 119.9 | C14—C15—H15 | 120.0 |
C45—C44—C43 | 120.6 (3) | C16—C15—H15 | 120.0 |
C45—C44—H44 | 119.7 | C15—C16—C11 | 121.6 (3) |
C43—C44—H44 | 119.7 | C15—C16—H16 | 119.2 |
C44—C45—C46 | 119.1 (3) | C11—C16—H16 | 119.2 |
C44—C45—H45 | 120.4 | C26—C21—C22 | 118.7 (3) |
C46—C45—H45 | 120.4 | C26—C21—P1 | 122.6 (2) |
C45—C46—C41 | 122.1 (3) | C22—C21—P1 | 118.4 (2) |
C45—C46—H46 | 119.0 | C23—C22—C21 | 120.3 (4) |
C41—C46—H46 | 119.0 | C23—C22—H22 | 119.8 |
C56—C51—C52 | 118.3 (3) | C21—C22—H22 | 119.8 |
C56—C51—P2 | 124.2 (2) | C24—C23—C22 | 120.3 (4) |
C52—C51—P2 | 117.5 (2) | C24—C23—H23 | 119.9 |
C51—C52—C53 | 120.9 (3) | C22—C23—H23 | 119.9 |
C51—C52—H52 | 119.6 | C23—C24—C25 | 120.2 (3) |
C53—C52—H52 | 119.6 | C23—C24—H24 | 119.9 |
C54—C53—C52 | 119.8 (3) | C25—C24—H24 | 119.9 |
C54—C53—H53 | 120.1 | C24—C25—C26 | 120.0 (4) |
C52—C53—H53 | 120.1 | C24—C25—H25 | 120.0 |
C53—C54—C55 | 120.0 (3) | C26—C25—H25 | 120.0 |
C53—C54—H54 | 120.0 | C21—C26—C25 | 120.5 (3) |
C55—C54—H54 | 120.0 | C21—C26—H26 | 119.8 |
C54—C55—C56 | 120.1 (3) | C25—C26—H26 | 119.8 |
C54—C55—H55 | 120.0 | C36—C31—C32 | 117.8 (3) |
C56—C55—H55 | 120.0 | C36—C31—P1 | 119.8 (2) |
C55—C56—C51 | 120.9 (3) | C32—C31—P1 | 122.5 (2) |
C55—C56—H56 | 119.6 | C33—C32—C31 | 121.7 (3) |
C51—C56—H56 | 119.6 | C33—C32—H32 | 119.2 |
C66—C61—C62 | 117.5 (3) | C31—C32—H32 | 119.2 |
C66—C61—P2 | 124.6 (2) | C32—C33—C34 | 119.7 (3) |
C62—C61—P2 | 117.9 (2) | C32—C33—H33 | 120.2 |
C63—C62—C61 | 121.2 (3) | C34—C33—H33 | 120.2 |
C63—C62—H62 | 119.4 | C35—C34—C33 | 120.2 (3) |
C61—C62—H62 | 119.4 | C35—C34—H34 | 119.9 |
C62—C63—C64 | 120.2 (3) | C33—C34—H34 | 119.9 |
C62—C63—H63 | 119.9 | C34—C35—C36 | 119.5 (3) |
C64—C63—H63 | 119.9 | C34—C35—H35 | 120.2 |
C65—C64—C63 | 119.6 (3) | C36—C35—H35 | 120.2 |
C65—C64—H64 | 120.2 | C31—C36—C35 | 121.2 (3) |
C63—C64—H64 | 120.2 | C31—C36—H36 | 119.4 |
C64—C65—C66 | 120.9 (3) | C35—C36—H36 | 119.4 |
C64—C65—H65 | 119.5 | C21—P1—C11 | 109.24 (13) |
C66—C65—H65 | 119.5 | C21—P1—C31 | 102.63 (13) |
C65—C66—C61 | 120.6 (3) | C11—P1—C31 | 105.41 (13) |
C65—C66—H66 | 119.7 | C21—P1—S1 | 114.07 (11) |
C61—C66—H66 | 119.7 | C11—P1—S1 | 112.23 (9) |
C16—C11—C12 | 117.9 (3) | C31—P1—S1 | 112.52 (10) |
C16—C11—P1 | 119.0 (2) | C61—P2—C51 | 101.84 (12) |
C12—C11—P1 | 122.4 (2) | C61—P2—C41 | 101.92 (12) |
C13—C12—C11 | 119.7 (3) | C51—P2—C41 | 100.97 (13) |
C13—C12—S2 | 119.4 (2) | C12—S2—C42 | 101.92 (13) |
C46—C41—C42—C43 | 2.1 (4) | P1—C21—C26—C25 | 174.3 (3) |
P2—C41—C42—C43 | −178.3 (2) | C24—C25—C26—C21 | −0.4 (5) |
C46—C41—C42—S2 | −176.8 (2) | C36—C31—C32—C33 | 0.5 (5) |
P2—C41—C42—S2 | 2.7 (3) | P1—C31—C32—C33 | −178.8 (3) |
C41—C42—C43—C44 | −0.8 (4) | C31—C32—C33—C34 | 0.0 (5) |
S2—C42—C43—C44 | 178.1 (2) | C32—C33—C34—C35 | −0.6 (5) |
C42—C43—C44—C45 | −0.6 (4) | C33—C34—C35—C36 | 0.6 (5) |
C43—C44—C45—C46 | 0.6 (5) | C32—C31—C36—C35 | −0.6 (4) |
C44—C45—C46—C41 | 0.9 (5) | P1—C31—C36—C35 | 178.8 (2) |
C42—C41—C46—C45 | −2.2 (4) | C34—C35—C36—C31 | 0.0 (5) |
P2—C41—C46—C45 | 178.3 (2) | C26—C21—P1—C11 | 30.5 (3) |
C56—C51—C52—C53 | 1.9 (4) | C22—C21—P1—C11 | −154.9 (2) |
P2—C51—C52—C53 | −179.2 (2) | C26—C21—P1—C31 | −81.0 (3) |
C51—C52—C53—C54 | −1.4 (5) | C22—C21—P1—C31 | 93.6 (3) |
C52—C53—C54—C55 | −0.4 (5) | C26—C21—P1—S1 | 157.0 (2) |
C53—C54—C55—C56 | 1.5 (5) | C22—C21—P1—S1 | −28.4 (3) |
C54—C55—C56—C51 | −1.0 (5) | C16—C11—P1—C21 | −126.7 (2) |
C52—C51—C56—C55 | −0.7 (4) | C12—C11—P1—C21 | 63.4 (2) |
P2—C51—C56—C55 | −179.6 (2) | C16—C11—P1—C31 | −17.1 (2) |
C66—C61—C62—C63 | 1.6 (5) | C12—C11—P1—C31 | 173.0 (2) |
P2—C61—C62—C63 | 179.5 (2) | C16—C11—P1—S1 | 105.7 (2) |
C61—C62—C63—C64 | −1.2 (5) | C12—C11—P1—S1 | −64.1 (2) |
C62—C63—C64—C65 | 0.1 (5) | C36—C31—P1—C21 | −137.5 (2) |
C63—C64—C65—C66 | 0.6 (6) | C32—C31—P1—C21 | 41.8 (3) |
C64—C65—C66—C61 | −0.2 (5) | C36—C31—P1—C11 | 108.2 (2) |
C62—C61—C66—C65 | −0.8 (5) | C32—C31—P1—C11 | −72.5 (3) |
P2—C61—C66—C65 | −178.6 (2) | C36—C31—P1—S1 | −14.4 (3) |
C16—C11—C12—C13 | 0.0 (4) | C32—C31—P1—S1 | 164.9 (2) |
P1—C11—C12—C13 | 170.0 (2) | C66—C61—P2—C51 | 11.4 (3) |
C16—C11—C12—S2 | −176.8 (2) | C62—C61—P2—C51 | −166.4 (2) |
P1—C11—C12—S2 | −6.9 (3) | C66—C61—P2—C41 | −92.7 (3) |
C11—C12—C13—C14 | 0.7 (4) | C62—C61—P2—C41 | 89.6 (3) |
S2—C12—C13—C14 | 177.6 (2) | C56—C51—P2—C61 | −99.5 (2) |
C12—C13—C14—C15 | −0.4 (4) | C52—C51—P2—C61 | 81.6 (2) |
C13—C14—C15—C16 | −0.6 (5) | C56—C51—P2—C41 | 5.3 (3) |
C14—C15—C16—C11 | 1.3 (5) | C52—C51—P2—C41 | −173.6 (2) |
C12—C11—C16—C15 | −1.0 (4) | C46—C41—P2—C61 | 6.1 (3) |
P1—C11—C16—C15 | −171.3 (2) | C42—C41—P2—C61 | −173.4 (2) |
C26—C21—C22—C23 | 0.9 (5) | C46—C41—P2—C51 | −98.7 (2) |
P1—C21—C22—C23 | −173.9 (3) | C42—C41—P2—C51 | 81.9 (2) |
C21—C22—C23—C24 | −0.9 (5) | C13—C12—S2—C42 | 57.4 (2) |
C22—C23—C24—C25 | 0.2 (6) | C11—C12—S2—C42 | −125.8 (2) |
C23—C24—C25—C26 | 0.4 (6) | C43—C42—S2—C12 | 26.4 (3) |
C22—C21—C26—C25 | −0.2 (5) | C41—C42—S2—C12 | −154.7 (2) |
Cg is the centroid of the C41–C46 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···Cgi | 0.93 | 2.94 | 3.777 (4) | 150 |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C36H28P2S2 |
Mr | 586.64 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 10.8595 (10), 11.0267 (10), 13.3031 (12) |
α, β, γ (°) | 76.404 (2), 79.151 (2), 81.976 (2) |
V (Å3) | 1513.1 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.34 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.806, 0.941 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10362, 6991, 4414 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.680 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.135, 0.98 |
No. of reflections | 6991 |
No. of parameters | 361 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.46, −0.29 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).
Cg is the centroid of the C41–C46 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···Cgi | 0.93 | 2.94 | 3.777 (4) | 150 |
Symmetry code: (i) −x+1, −y+1, −z. |
Acknowledgements
FMC thanks the Ministerio de Educación y Ciencia of Spain for a grant.
References
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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.
Metal complexes of hemilabile ligands have been studied in the last few years due to their importance in homogeneous catalysis (Deb et al., 2010; Dallanegra et al., 2012; Marimuthu et al., 2012). The phosphine derivatives (Ia,b), (IIa-d), and (IIIa-f) are a set of hemilabile ligands where the nature of the heteroatoms determines their coordinating ability towards soft or hard metals (Fig. 1). Crystal structures of (Ia), (IIa,b), and (IIIa) have been described (Pintado-Alba et al., 2004; Tooke et al., 2005; Deb et al., 2010; Deb and Dutta, 2010). Here we present the structure of (IId). The molecular structure is shown in Fig. 2. The ability of this molecule to act as a ligand is related to its conformational freedom. The S(hinge)···S(arm) distance depends on the torsional angle C12—C11—P1═S1 whereas the S(arm)···P distance depends also on C11—C12—S2—C42 and C12—S2—C42—C41. In this way, the ligand can be coordinated to metals of different sizes. Values found in (IId) for the above torsional angles are -64.1 (2)°, -125.8 (2)° and -154.7 (2)° respectively. In this conformation, distances between coordinating positions are S1···S2 = 3.6803 (12) Å, S2···P2 = 3.1308 (11) Å, and S1···P2 = 6.0924 (13) Å.