In the crystal structure of the title compound, C21H21PS3, two crystallographically independent molecules are found. One of these molecules is located in a general position, whereas the P atom of the second molecule is located on a threefold rotation axis.
Supporting information
CCDC reference: 283760
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.004 Å
- R factor = 0.054
- wR factor = 0.135
- Data-to-parameter ratio = 21.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 145.00 A 3
Alert level C
DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 1.518
Test value = 1.200
DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.65
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 1.52 e/A 3
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.72 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C24 - C25 .. 5.67 su
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: IPDS (Stoe & Cie, 1998); cell refinement: IPDS; data reduction: IPDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: CIFTAB in SHELXL97.
Tris[2-(methylsulfanyl)phenyl]phosphine
top
Crystal data top
C21H21PS3 | Dx = 1.319 Mg m−3 |
Mr = 400.53 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3 | Cell parameters from 7998 reflections |
Hall symbol: -R 3 | θ = 12.5–23° |
a = 23.4523 (15) Å | µ = 0.45 mm−1 |
c = 25.4022 (18) Å | T = 170 K |
V = 12099.6 (14) Å3 | Block, colourless |
Z = 24 | 0.3 × 0.25 × 0.25 mm |
F(000) = 5040 | |
Data collection top
Stoe IPDS-1 diffractometer | 5279 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 28.0°, θmin = 2.8° |
φ scans | h = −30→30 |
34061 measured reflections | k = −30→30 |
6469 independent reflections | l = −33→33 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0594P)2 + 57.688P] where P = (Fo2 + 2Fc2)/3 |
6469 reflections | (Δ/σ)max = 0.001 |
301 parameters | Δρmax = 1.52 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.51266 (3) | 0.45658 (3) | 0.69623 (2) | 0.02139 (15) | |
C1 | 0.43921 (13) | 0.37446 (12) | 0.69091 (9) | 0.0218 (5) | |
C2 | 0.37735 (13) | 0.36515 (12) | 0.70739 (9) | 0.0224 (5) | |
C3 | 0.32066 (14) | 0.30435 (13) | 0.70169 (11) | 0.0289 (6) | |
H3 | 0.2798 | 0.2979 | 0.7145 | 0.035* | |
C4 | 0.32349 (15) | 0.25270 (14) | 0.67714 (12) | 0.0339 (6) | |
H4 | 0.2844 | 0.2115 | 0.6723 | 0.041* | |
C5 | 0.38259 (16) | 0.26147 (14) | 0.66005 (11) | 0.0352 (6) | |
H5 | 0.3843 | 0.2263 | 0.6430 | 0.042* | |
C6 | 0.44014 (15) | 0.32115 (13) | 0.66724 (10) | 0.0276 (5) | |
H6 | 0.4809 | 0.3258 | 0.6559 | 0.033* | |
S1 | 0.37626 (4) | 0.43366 (4) | 0.73565 (3) | 0.03288 (17) | |
C7 | 0.29011 (16) | 0.40440 (17) | 0.74383 (14) | 0.0428 (7) | |
H7A | 0.2841 | 0.4392 | 0.7596 | 0.064* | |
H7B | 0.2709 | 0.3658 | 0.7670 | 0.064* | |
H7C | 0.2683 | 0.3923 | 0.7094 | 0.064* | |
C11 | 0.57859 (13) | 0.44365 (13) | 0.67020 (10) | 0.0247 (5) | |
C12 | 0.58826 (13) | 0.44396 (13) | 0.61566 (10) | 0.0251 (5) | |
C13 | 0.64102 (14) | 0.43905 (15) | 0.59571 (12) | 0.0323 (6) | |
H13 | 0.6464 | 0.4380 | 0.5587 | 0.039* | |
C14 | 0.68578 (16) | 0.43570 (17) | 0.62950 (13) | 0.0385 (7) | |
H14 | 0.7220 | 0.4331 | 0.6157 | 0.046* | |
C15 | 0.67745 (17) | 0.43615 (19) | 0.68329 (13) | 0.0444 (8) | |
H15 | 0.7080 | 0.4340 | 0.7067 | 0.053* | |
C16 | 0.62523 (15) | 0.43966 (15) | 0.70243 (11) | 0.0343 (6) | |
H16 | 0.6199 | 0.4394 | 0.7395 | 0.041* | |
S2 | 0.52944 (4) | 0.44698 (4) | 0.57320 (3) | 0.03663 (19) | |
C17 | 0.57505 (15) | 0.47832 (15) | 0.51307 (11) | 0.0345 (6) | |
H17A | 0.5469 | 0.4820 | 0.4864 | 0.052* | |
H17B | 0.5897 | 0.4482 | 0.5005 | 0.052* | |
H17C | 0.6135 | 0.5218 | 0.5195 | 0.052* | |
C21 | 0.52869 (12) | 0.46206 (13) | 0.76742 (10) | 0.0238 (5) | |
C22 | 0.56950 (12) | 0.52423 (14) | 0.79038 (10) | 0.0261 (5) | |
C23 | 0.57700 (14) | 0.53094 (18) | 0.84464 (11) | 0.0381 (7) | |
H23 | 0.6032 | 0.5732 | 0.8600 | 0.046* | |
C24 | 0.54551 (16) | 0.4748 (2) | 0.87647 (11) | 0.0485 (9) | |
H24 | 0.5505 | 0.4785 | 0.9136 | 0.058* | |
C25 | 0.50718 (15) | 0.41413 (18) | 0.85336 (12) | 0.0447 (9) | |
H25 | 0.4860 | 0.3761 | 0.8750 | 0.054* | |
C26 | 0.49894 (15) | 0.40736 (16) | 0.80014 (11) | 0.0382 (7) | |
H26 | 0.4726 | 0.3648 | 0.7853 | 0.046* | |
S3 | 0.61283 (3) | 0.59034 (3) | 0.74626 (3) | 0.03353 (17) | |
C27 | 0.65616 (18) | 0.66151 (17) | 0.78796 (19) | 0.0593 (11) | |
H27A | 0.6816 | 0.7007 | 0.7661 | 0.089* | |
H27B | 0.6860 | 0.6554 | 0.8113 | 0.089* | |
H27C | 0.6244 | 0.6671 | 0.8092 | 0.089* | |
P2 | 0.3333 | 0.6667 | 0.80038 (4) | 0.0162 (2) | |
C31 | 0.40202 (11) | 0.66402 (11) | 0.76817 (9) | 0.0167 (4) | |
C32 | 0.42020 (11) | 0.61806 (11) | 0.78545 (9) | 0.0183 (4) | |
C33 | 0.47485 (12) | 0.61832 (12) | 0.76346 (10) | 0.0221 (5) | |
H33 | 0.4867 | 0.5870 | 0.7749 | 0.027* | |
C34 | 0.51213 (12) | 0.66402 (13) | 0.72502 (10) | 0.0233 (5) | |
H34 | 0.5498 | 0.6644 | 0.7108 | 0.028* | |
C35 | 0.49475 (12) | 0.70913 (12) | 0.70729 (9) | 0.0215 (5) | |
H35 | 0.5201 | 0.7402 | 0.6808 | 0.026* | |
C36 | 0.43992 (12) | 0.70863 (12) | 0.72854 (9) | 0.0194 (5) | |
H36 | 0.4278 | 0.7392 | 0.7159 | 0.023* | |
S4 | 0.36891 (3) | 0.55893 (3) | 0.83254 (3) | 0.02691 (15) | |
C37 | 0.42004 (15) | 0.52982 (15) | 0.86033 (11) | 0.0320 (6) | |
H37A | 0.3951 | 0.4963 | 0.8871 | 0.048* | |
H37B | 0.4589 | 0.5667 | 0.8766 | 0.048* | |
H37C | 0.4340 | 0.5105 | 0.8325 | 0.048* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0263 (3) | 0.0204 (3) | 0.0157 (3) | 0.0104 (3) | 0.0016 (2) | 0.0007 (2) |
C1 | 0.0273 (12) | 0.0215 (11) | 0.0159 (10) | 0.0117 (10) | −0.0023 (9) | 0.0009 (9) |
C2 | 0.0297 (13) | 0.0259 (12) | 0.0152 (10) | 0.0167 (11) | −0.0023 (9) | 0.0012 (9) |
C3 | 0.0267 (13) | 0.0258 (13) | 0.0303 (13) | 0.0103 (11) | −0.0041 (11) | 0.0012 (10) |
C4 | 0.0377 (16) | 0.0216 (13) | 0.0367 (15) | 0.0105 (12) | −0.0071 (12) | 0.0022 (11) |
C5 | 0.0474 (18) | 0.0260 (14) | 0.0307 (14) | 0.0172 (13) | −0.0005 (13) | −0.0005 (11) |
C6 | 0.0392 (15) | 0.0232 (12) | 0.0237 (12) | 0.0180 (11) | 0.0026 (11) | 0.0031 (10) |
S1 | 0.0335 (4) | 0.0325 (4) | 0.0370 (4) | 0.0197 (3) | −0.0036 (3) | −0.0110 (3) |
C7 | 0.0370 (17) | 0.0462 (18) | 0.0512 (19) | 0.0254 (15) | 0.0103 (14) | 0.0026 (15) |
C11 | 0.0263 (12) | 0.0239 (12) | 0.0220 (12) | 0.0110 (10) | 0.0002 (10) | 0.0009 (10) |
C12 | 0.0231 (12) | 0.0239 (12) | 0.0262 (12) | 0.0101 (10) | 0.0012 (10) | 0.0005 (10) |
C13 | 0.0318 (14) | 0.0349 (15) | 0.0289 (14) | 0.0157 (12) | 0.0061 (11) | 0.0000 (11) |
C14 | 0.0346 (16) | 0.0459 (18) | 0.0425 (17) | 0.0258 (14) | 0.0066 (13) | 0.0001 (14) |
C15 | 0.0447 (18) | 0.060 (2) | 0.0409 (17) | 0.0356 (17) | −0.0071 (14) | −0.0007 (15) |
C16 | 0.0400 (16) | 0.0436 (17) | 0.0269 (13) | 0.0266 (14) | −0.0113 (12) | −0.0004 (12) |
S2 | 0.0309 (4) | 0.0617 (5) | 0.0190 (3) | 0.0244 (4) | 0.0031 (3) | 0.0023 (3) |
C17 | 0.0404 (16) | 0.0401 (16) | 0.0239 (13) | 0.0207 (14) | 0.0045 (12) | 0.0045 (12) |
C21 | 0.0206 (12) | 0.0285 (13) | 0.0179 (11) | 0.0089 (10) | −0.0001 (9) | −0.0027 (9) |
C22 | 0.0154 (11) | 0.0325 (14) | 0.0291 (13) | 0.0111 (10) | −0.0016 (9) | −0.0098 (11) |
C23 | 0.0214 (13) | 0.059 (2) | 0.0301 (14) | 0.0176 (13) | −0.0066 (11) | −0.0215 (14) |
C24 | 0.0306 (15) | 0.086 (3) | 0.0160 (12) | 0.0193 (17) | −0.0015 (11) | −0.0057 (15) |
C25 | 0.0240 (14) | 0.053 (2) | 0.0268 (14) | −0.0036 (13) | 0.0004 (11) | 0.0110 (13) |
C26 | 0.0337 (15) | 0.0348 (16) | 0.0253 (13) | 0.0015 (13) | −0.0041 (11) | 0.0057 (12) |
S3 | 0.0262 (3) | 0.0225 (3) | 0.0478 (4) | 0.0091 (3) | −0.0025 (3) | 0.0000 (3) |
C27 | 0.0402 (19) | 0.0295 (17) | 0.103 (3) | 0.0132 (15) | −0.021 (2) | −0.0267 (19) |
P2 | 0.0173 (3) | 0.0173 (3) | 0.0140 (4) | 0.00867 (14) | 0.000 | 0.000 |
C31 | 0.0163 (10) | 0.0186 (11) | 0.0151 (10) | 0.0085 (9) | −0.0020 (8) | −0.0011 (8) |
C32 | 0.0163 (10) | 0.0186 (11) | 0.0186 (10) | 0.0077 (9) | −0.0012 (8) | 0.0002 (8) |
C33 | 0.0214 (11) | 0.0222 (12) | 0.0253 (12) | 0.0128 (10) | 0.0001 (9) | 0.0021 (9) |
C34 | 0.0204 (11) | 0.0299 (13) | 0.0215 (11) | 0.0140 (10) | 0.0026 (9) | −0.0001 (10) |
C35 | 0.0240 (12) | 0.0241 (12) | 0.0158 (10) | 0.0114 (10) | 0.0033 (9) | 0.0009 (9) |
C36 | 0.0217 (11) | 0.0209 (11) | 0.0161 (10) | 0.0111 (9) | 0.0008 (9) | 0.0008 (8) |
S4 | 0.0238 (3) | 0.0262 (3) | 0.0311 (3) | 0.0129 (3) | 0.0050 (2) | 0.0132 (3) |
C37 | 0.0413 (16) | 0.0365 (15) | 0.0260 (13) | 0.0254 (13) | −0.0010 (11) | 0.0073 (11) |
Geometric parameters (Å, º) top
P1—C1 | 1.838 (3) | C21—C26 | 1.389 (4) |
P1—C21 | 1.838 (3) | C21—C22 | 1.409 (4) |
P1—C11 | 1.841 (3) | C22—C23 | 1.389 (4) |
C1—C6 | 1.397 (4) | C22—S3 | 1.765 (3) |
C1—C2 | 1.418 (4) | C23—C24 | 1.400 (5) |
C2—C3 | 1.388 (4) | C23—H23 | 0.9500 |
C2—S1 | 1.772 (3) | C24—C25 | 1.378 (5) |
C3—C4 | 1.393 (4) | C24—H24 | 0.9500 |
C3—H3 | 0.9500 | C25—C26 | 1.364 (4) |
C4—C5 | 1.366 (5) | C25—H25 | 0.9500 |
C4—H4 | 0.9500 | C26—H26 | 0.9500 |
C5—C6 | 1.387 (4) | S3—C27 | 1.801 (3) |
C5—H5 | 0.9500 | C27—H27A | 0.9800 |
C6—H6 | 0.9500 | C27—H27B | 0.9800 |
S1—C7 | 1.792 (3) | C27—H27C | 0.9800 |
C7—H7A | 0.9800 | P2—C31i | 1.835 (2) |
C7—H7B | 0.9800 | P2—C31ii | 1.835 (2) |
C7—H7C | 0.9800 | P2—C31 | 1.835 (2) |
C11—C12 | 1.403 (4) | C31—C36 | 1.403 (3) |
C11—C16 | 1.406 (4) | C31—C32 | 1.413 (3) |
C12—C13 | 1.394 (4) | C32—C33 | 1.395 (3) |
C12—S2 | 1.780 (3) | C32—S4 | 1.770 (2) |
C13—C14 | 1.388 (4) | C33—C34 | 1.389 (3) |
C13—H13 | 0.9500 | C33—H33 | 0.9500 |
C14—C15 | 1.381 (5) | C34—C35 | 1.385 (4) |
C14—H14 | 0.9500 | C34—H34 | 0.9500 |
C15—C16 | 1.358 (4) | C35—C36 | 1.389 (3) |
C15—H15 | 0.9500 | C35—H35 | 0.9500 |
C16—H16 | 0.9500 | C36—H36 | 0.9500 |
S2—C17 | 1.798 (3) | S4—C37 | 1.795 (3) |
C17—H17A | 0.9800 | C37—H37A | 0.9800 |
C17—H17B | 0.9800 | C37—H37B | 0.9800 |
C17—H17C | 0.9800 | C37—H37C | 0.9800 |
| | | |
C1—P1—C21 | 101.39 (11) | C26—C21—C22 | 118.4 (2) |
C1—P1—C11 | 103.03 (12) | C26—C21—P1 | 122.2 (2) |
C21—P1—C11 | 101.87 (12) | C22—C21—P1 | 119.3 (2) |
C6—C1—C2 | 117.5 (2) | C23—C22—C21 | 120.7 (3) |
C6—C1—P1 | 122.9 (2) | C23—C22—S3 | 123.1 (2) |
C2—C1—P1 | 119.37 (19) | C21—C22—S3 | 116.2 (2) |
C3—C2—C1 | 120.5 (2) | C22—C23—C24 | 119.3 (3) |
C3—C2—S1 | 122.2 (2) | C22—C23—H23 | 120.3 |
C1—C2—S1 | 117.23 (19) | C24—C23—H23 | 120.3 |
C2—C3—C4 | 120.2 (3) | C25—C24—C23 | 119.3 (3) |
C2—C3—H3 | 119.9 | C25—C24—H24 | 120.3 |
C4—C3—H3 | 119.9 | C23—C24—H24 | 120.3 |
C5—C4—C3 | 119.8 (3) | C26—C25—C24 | 121.6 (3) |
C5—C4—H4 | 120.1 | C26—C25—H25 | 119.2 |
C3—C4—H4 | 120.1 | C24—C25—H25 | 119.2 |
C4—C5—C6 | 120.8 (3) | C25—C26—C21 | 120.6 (3) |
C4—C5—H5 | 119.6 | C25—C26—H26 | 119.7 |
C6—C5—H5 | 119.6 | C21—C26—H26 | 119.7 |
C5—C6—C1 | 121.1 (3) | C22—S3—C27 | 104.53 (18) |
C5—C6—H6 | 119.4 | S3—C27—H27A | 109.5 |
C1—C6—H6 | 119.4 | S3—C27—H27B | 109.5 |
C2—S1—C7 | 102.98 (15) | H27A—C27—H27B | 109.5 |
S1—C7—H7A | 109.5 | S3—C27—H27C | 109.5 |
S1—C7—H7B | 109.5 | H27A—C27—H27C | 109.5 |
H7A—C7—H7B | 109.5 | H27B—C27—H27C | 109.5 |
S1—C7—H7C | 109.5 | C31i—P2—C31ii | 101.65 (9) |
H7A—C7—H7C | 109.5 | C31i—P2—C31 | 101.65 (9) |
H7B—C7—H7C | 109.5 | C31ii—P2—C31 | 101.65 (9) |
C12—C11—C16 | 116.5 (2) | C36—C31—C32 | 118.1 (2) |
C12—C11—P1 | 120.0 (2) | C36—C31—P2 | 122.29 (17) |
C16—C11—P1 | 123.2 (2) | C32—C31—P2 | 119.49 (17) |
C13—C12—C11 | 120.4 (3) | C33—C32—C31 | 120.0 (2) |
C13—C12—S2 | 121.4 (2) | C33—C32—S4 | 122.47 (18) |
C11—C12—S2 | 118.2 (2) | C31—C32—S4 | 117.48 (17) |
C14—C13—C12 | 120.5 (3) | C34—C33—C32 | 120.5 (2) |
C14—C13—H13 | 119.8 | C34—C33—H33 | 119.8 |
C12—C13—H13 | 119.8 | C32—C33—H33 | 119.8 |
C15—C14—C13 | 119.8 (3) | C35—C34—C33 | 120.4 (2) |
C15—C14—H14 | 120.1 | C35—C34—H34 | 119.8 |
C13—C14—H14 | 120.1 | C33—C34—H34 | 119.8 |
C16—C15—C14 | 119.3 (3) | C34—C35—C36 | 119.5 (2) |
C16—C15—H15 | 120.3 | C34—C35—H35 | 120.3 |
C14—C15—H15 | 120.3 | C36—C35—H35 | 120.3 |
C15—C16—C11 | 123.4 (3) | C35—C36—C31 | 121.6 (2) |
C15—C16—H16 | 118.3 | C35—C36—H36 | 119.2 |
C11—C16—H16 | 118.3 | C31—C36—H36 | 119.2 |
C12—S2—C17 | 102.52 (14) | C32—S4—C37 | 104.02 (13) |
S2—C17—H17A | 109.5 | S4—C37—H37A | 109.5 |
S2—C17—H17B | 109.5 | S4—C37—H37B | 109.5 |
H17A—C17—H17B | 109.5 | H37A—C37—H37B | 109.5 |
S2—C17—H17C | 109.5 | S4—C37—H37C | 109.5 |
H17A—C17—H17C | 109.5 | H37A—C37—H37C | 109.5 |
H17B—C17—H17C | 109.5 | H37B—C37—H37C | 109.5 |
Symmetry codes: (i) −y+1, x−y+1, z; (ii) −x+y, −x+1, z. |