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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025602/bt6715sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025602/bt6715Isup2.hkl
Contains datablock I

CCDC reference: 283760

Key indicators

  • Single-crystal X-ray study
  • T = 170 K
  • Mean [sigma](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

Computing details top

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
C21H21PS3Dx = 1.319 Mg m3
Mr = 400.53Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 7998 reflections
Hall symbol: -R 3θ = 12.5–23°
a = 23.4523 (15) ŵ = 0.45 mm1
c = 25.4022 (18) ÅT = 170 K
V = 12099.6 (14) Å3Block, colourless
Z = 240.3 × 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 tubeRint = 0.045
Graphite monochromatorθmax = 28.0°, θmin = 2.8°
φ scansh = 3030
34061 measured reflectionsk = 3030
6469 independent reflectionsl = 3333
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-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 parametersΔρmax = 1.52 e Å3
0 restraintsΔρmin = 0.57 e Å3
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
xyzUiso*/Ueq
P10.51266 (3)0.45658 (3)0.69623 (2)0.02139 (15)
C10.43921 (13)0.37446 (12)0.69091 (9)0.0218 (5)
C20.37735 (13)0.36515 (12)0.70739 (9)0.0224 (5)
C30.32066 (14)0.30435 (13)0.70169 (11)0.0289 (6)
H30.27980.29790.71450.035*
C40.32349 (15)0.25270 (14)0.67714 (12)0.0339 (6)
H40.28440.21150.67230.041*
C50.38259 (16)0.26147 (14)0.66005 (11)0.0352 (6)
H50.38430.22630.64300.042*
C60.44014 (15)0.32115 (13)0.66724 (10)0.0276 (5)
H60.48090.32580.65590.033*
S10.37626 (4)0.43366 (4)0.73565 (3)0.03288 (17)
C70.29011 (16)0.40440 (17)0.74383 (14)0.0428 (7)
H7A0.28410.43920.75960.064*
H7B0.27090.36580.76700.064*
H7C0.26830.39230.70940.064*
C110.57859 (13)0.44365 (13)0.67020 (10)0.0247 (5)
C120.58826 (13)0.44396 (13)0.61566 (10)0.0251 (5)
C130.64102 (14)0.43905 (15)0.59571 (12)0.0323 (6)
H130.64640.43800.55870.039*
C140.68578 (16)0.43570 (17)0.62950 (13)0.0385 (7)
H140.72200.43310.61570.046*
C150.67745 (17)0.43615 (19)0.68329 (13)0.0444 (8)
H150.70800.43400.70670.053*
C160.62523 (15)0.43966 (15)0.70243 (11)0.0343 (6)
H160.61990.43940.73950.041*
S20.52944 (4)0.44698 (4)0.57320 (3)0.03663 (19)
C170.57505 (15)0.47832 (15)0.51307 (11)0.0345 (6)
H17A0.54690.48200.48640.052*
H17B0.58970.44820.50050.052*
H17C0.61350.52180.51950.052*
C210.52869 (12)0.46206 (13)0.76742 (10)0.0238 (5)
C220.56950 (12)0.52423 (14)0.79038 (10)0.0261 (5)
C230.57700 (14)0.53094 (18)0.84464 (11)0.0381 (7)
H230.60320.57320.86000.046*
C240.54551 (16)0.4748 (2)0.87647 (11)0.0485 (9)
H240.55050.47850.91360.058*
C250.50718 (15)0.41413 (18)0.85336 (12)0.0447 (9)
H250.48600.37610.87500.054*
C260.49894 (15)0.40736 (16)0.80014 (11)0.0382 (7)
H260.47260.36480.78530.046*
S30.61283 (3)0.59034 (3)0.74626 (3)0.03353 (17)
C270.65616 (18)0.66151 (17)0.78796 (19)0.0593 (11)
H27A0.68160.70070.76610.089*
H27B0.68600.65540.81130.089*
H27C0.62440.66710.80920.089*
P20.33330.66670.80038 (4)0.0162 (2)
C310.40202 (11)0.66402 (11)0.76817 (9)0.0167 (4)
C320.42020 (11)0.61806 (11)0.78545 (9)0.0183 (4)
C330.47485 (12)0.61832 (12)0.76346 (10)0.0221 (5)
H330.48670.58700.77490.027*
C340.51213 (12)0.66402 (13)0.72502 (10)0.0233 (5)
H340.54980.66440.71080.028*
C350.49475 (12)0.70913 (12)0.70729 (9)0.0215 (5)
H350.52010.74020.68080.026*
C360.43992 (12)0.70863 (12)0.72854 (9)0.0194 (5)
H360.42780.73920.71590.023*
S40.36891 (3)0.55893 (3)0.83254 (3)0.02691 (15)
C370.42004 (15)0.52982 (15)0.86033 (11)0.0320 (6)
H37A0.39510.49630.88710.048*
H37B0.45890.56670.87660.048*
H37C0.43400.51050.83250.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0263 (3)0.0204 (3)0.0157 (3)0.0104 (3)0.0016 (2)0.0007 (2)
C10.0273 (12)0.0215 (11)0.0159 (10)0.0117 (10)0.0023 (9)0.0009 (9)
C20.0297 (13)0.0259 (12)0.0152 (10)0.0167 (11)0.0023 (9)0.0012 (9)
C30.0267 (13)0.0258 (13)0.0303 (13)0.0103 (11)0.0041 (11)0.0012 (10)
C40.0377 (16)0.0216 (13)0.0367 (15)0.0105 (12)0.0071 (12)0.0022 (11)
C50.0474 (18)0.0260 (14)0.0307 (14)0.0172 (13)0.0005 (13)0.0005 (11)
C60.0392 (15)0.0232 (12)0.0237 (12)0.0180 (11)0.0026 (11)0.0031 (10)
S10.0335 (4)0.0325 (4)0.0370 (4)0.0197 (3)0.0036 (3)0.0110 (3)
C70.0370 (17)0.0462 (18)0.0512 (19)0.0254 (15)0.0103 (14)0.0026 (15)
C110.0263 (12)0.0239 (12)0.0220 (12)0.0110 (10)0.0002 (10)0.0009 (10)
C120.0231 (12)0.0239 (12)0.0262 (12)0.0101 (10)0.0012 (10)0.0005 (10)
C130.0318 (14)0.0349 (15)0.0289 (14)0.0157 (12)0.0061 (11)0.0000 (11)
C140.0346 (16)0.0459 (18)0.0425 (17)0.0258 (14)0.0066 (13)0.0001 (14)
C150.0447 (18)0.060 (2)0.0409 (17)0.0356 (17)0.0071 (14)0.0007 (15)
C160.0400 (16)0.0436 (17)0.0269 (13)0.0266 (14)0.0113 (12)0.0004 (12)
S20.0309 (4)0.0617 (5)0.0190 (3)0.0244 (4)0.0031 (3)0.0023 (3)
C170.0404 (16)0.0401 (16)0.0239 (13)0.0207 (14)0.0045 (12)0.0045 (12)
C210.0206 (12)0.0285 (13)0.0179 (11)0.0089 (10)0.0001 (9)0.0027 (9)
C220.0154 (11)0.0325 (14)0.0291 (13)0.0111 (10)0.0016 (9)0.0098 (11)
C230.0214 (13)0.059 (2)0.0301 (14)0.0176 (13)0.0066 (11)0.0215 (14)
C240.0306 (15)0.086 (3)0.0160 (12)0.0193 (17)0.0015 (11)0.0057 (15)
C250.0240 (14)0.053 (2)0.0268 (14)0.0036 (13)0.0004 (11)0.0110 (13)
C260.0337 (15)0.0348 (16)0.0253 (13)0.0015 (13)0.0041 (11)0.0057 (12)
S30.0262 (3)0.0225 (3)0.0478 (4)0.0091 (3)0.0025 (3)0.0000 (3)
C270.0402 (19)0.0295 (17)0.103 (3)0.0132 (15)0.021 (2)0.0267 (19)
P20.0173 (3)0.0173 (3)0.0140 (4)0.00867 (14)0.0000.000
C310.0163 (10)0.0186 (11)0.0151 (10)0.0085 (9)0.0020 (8)0.0011 (8)
C320.0163 (10)0.0186 (11)0.0186 (10)0.0077 (9)0.0012 (8)0.0002 (8)
C330.0214 (11)0.0222 (12)0.0253 (12)0.0128 (10)0.0001 (9)0.0021 (9)
C340.0204 (11)0.0299 (13)0.0215 (11)0.0140 (10)0.0026 (9)0.0001 (10)
C350.0240 (12)0.0241 (12)0.0158 (10)0.0114 (10)0.0033 (9)0.0009 (9)
C360.0217 (11)0.0209 (11)0.0161 (10)0.0111 (9)0.0008 (9)0.0008 (8)
S40.0238 (3)0.0262 (3)0.0311 (3)0.0129 (3)0.0050 (2)0.0132 (3)
C370.0413 (16)0.0365 (15)0.0260 (13)0.0254 (13)0.0010 (11)0.0073 (11)
Geometric parameters (Å, º) top
P1—C11.838 (3)C21—C261.389 (4)
P1—C211.838 (3)C21—C221.409 (4)
P1—C111.841 (3)C22—C231.389 (4)
C1—C61.397 (4)C22—S31.765 (3)
C1—C21.418 (4)C23—C241.400 (5)
C2—C31.388 (4)C23—H230.9500
C2—S11.772 (3)C24—C251.378 (5)
C3—C41.393 (4)C24—H240.9500
C3—H30.9500C25—C261.364 (4)
C4—C51.366 (5)C25—H250.9500
C4—H40.9500C26—H260.9500
C5—C61.387 (4)S3—C271.801 (3)
C5—H50.9500C27—H27A0.9800
C6—H60.9500C27—H27B0.9800
S1—C71.792 (3)C27—H27C0.9800
C7—H7A0.9800P2—C31i1.835 (2)
C7—H7B0.9800P2—C31ii1.835 (2)
C7—H7C0.9800P2—C311.835 (2)
C11—C121.403 (4)C31—C361.403 (3)
C11—C161.406 (4)C31—C321.413 (3)
C12—C131.394 (4)C32—C331.395 (3)
C12—S21.780 (3)C32—S41.770 (2)
C13—C141.388 (4)C33—C341.389 (3)
C13—H130.9500C33—H330.9500
C14—C151.381 (5)C34—C351.385 (4)
C14—H140.9500C34—H340.9500
C15—C161.358 (4)C35—C361.389 (3)
C15—H150.9500C35—H350.9500
C16—H160.9500C36—H360.9500
S2—C171.798 (3)S4—C371.795 (3)
C17—H17A0.9800C37—H37A0.9800
C17—H17B0.9800C37—H37B0.9800
C17—H17C0.9800C37—H37C0.9800
C1—P1—C21101.39 (11)C26—C21—C22118.4 (2)
C1—P1—C11103.03 (12)C26—C21—P1122.2 (2)
C21—P1—C11101.87 (12)C22—C21—P1119.3 (2)
C6—C1—C2117.5 (2)C23—C22—C21120.7 (3)
C6—C1—P1122.9 (2)C23—C22—S3123.1 (2)
C2—C1—P1119.37 (19)C21—C22—S3116.2 (2)
C3—C2—C1120.5 (2)C22—C23—C24119.3 (3)
C3—C2—S1122.2 (2)C22—C23—H23120.3
C1—C2—S1117.23 (19)C24—C23—H23120.3
C2—C3—C4120.2 (3)C25—C24—C23119.3 (3)
C2—C3—H3119.9C25—C24—H24120.3
C4—C3—H3119.9C23—C24—H24120.3
C5—C4—C3119.8 (3)C26—C25—C24121.6 (3)
C5—C4—H4120.1C26—C25—H25119.2
C3—C4—H4120.1C24—C25—H25119.2
C4—C5—C6120.8 (3)C25—C26—C21120.6 (3)
C4—C5—H5119.6C25—C26—H26119.7
C6—C5—H5119.6C21—C26—H26119.7
C5—C6—C1121.1 (3)C22—S3—C27104.53 (18)
C5—C6—H6119.4S3—C27—H27A109.5
C1—C6—H6119.4S3—C27—H27B109.5
C2—S1—C7102.98 (15)H27A—C27—H27B109.5
S1—C7—H7A109.5S3—C27—H27C109.5
S1—C7—H7B109.5H27A—C27—H27C109.5
H7A—C7—H7B109.5H27B—C27—H27C109.5
S1—C7—H7C109.5C31i—P2—C31ii101.65 (9)
H7A—C7—H7C109.5C31i—P2—C31101.65 (9)
H7B—C7—H7C109.5C31ii—P2—C31101.65 (9)
C12—C11—C16116.5 (2)C36—C31—C32118.1 (2)
C12—C11—P1120.0 (2)C36—C31—P2122.29 (17)
C16—C11—P1123.2 (2)C32—C31—P2119.49 (17)
C13—C12—C11120.4 (3)C33—C32—C31120.0 (2)
C13—C12—S2121.4 (2)C33—C32—S4122.47 (18)
C11—C12—S2118.2 (2)C31—C32—S4117.48 (17)
C14—C13—C12120.5 (3)C34—C33—C32120.5 (2)
C14—C13—H13119.8C34—C33—H33119.8
C12—C13—H13119.8C32—C33—H33119.8
C15—C14—C13119.8 (3)C35—C34—C33120.4 (2)
C15—C14—H14120.1C35—C34—H34119.8
C13—C14—H14120.1C33—C34—H34119.8
C16—C15—C14119.3 (3)C34—C35—C36119.5 (2)
C16—C15—H15120.3C34—C35—H35120.3
C14—C15—H15120.3C36—C35—H35120.3
C15—C16—C11123.4 (3)C35—C36—C31121.6 (2)
C15—C16—H16118.3C35—C36—H36119.2
C11—C16—H16118.3C31—C36—H36119.2
C12—S2—C17102.52 (14)C32—S4—C37104.02 (13)
S2—C17—H17A109.5S4—C37—H37A109.5
S2—C17—H17B109.5S4—C37—H37B109.5
H17A—C17—H17B109.5H37A—C37—H37B109.5
S2—C17—H17C109.5S4—C37—H37C109.5
H17A—C17—H17C109.5H37A—C37—H37C109.5
H17B—C17—H17C109.5H37B—C37—H37C109.5
Symmetry codes: (i) y+1, xy+1, z; (ii) x+y, x+1, z.
 

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