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ISSN: 2056-9890

Tris[bis­­(2-methyl­prop­yl)di­thio­phosphinato]bis­­muth(III)

aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, bSchool of Chemistry and The Manchester Material Science Centre, The University of Manchester, Oxford Road, Manchester M13 9PL, England, and cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 24 April 2010; accepted 27 April 2010; online 8 May 2010)

The title compound, [Bi(C8H18PS2)3], contains a BiIII cation surrounded by three bis­(2-methyl­prop­yl)dithio­phosphinate anions, leading to a distorted octa­hedral coordination for the heavy metal. The Bi—S and S—P bond lengths are in the ranges 2.7694 (18)–2.8391 (17) and 2.019 (2)–2.035 (2) Å, respectively. The crystal structure is consolidated by C—H⋯S hydrogen bonds. Intra­molecular C—H⋯π inter­actions also play a role in stabilizing the mol­ecules.

Related literature

For applications of organodithio derivatives of phospho­rus compounds, see: Ebert et al. (1994[Ebert, K., Breunig, H., Silvestru, C., Stefan, I. & Haiduc, I. (1994). Inorg. Chem. 33, 1695-1699.]). For a related structure, see: Lawton et al. (1974[Lawton, S. L., Fuhrmeister, C. J., Haas, R. G., Jarman Jr, C. S. & Lohmeyer, F. G. (1974). Inorg. Chem. 13, 135-143.]).

[Scheme 1]

Experimental

Crystal data
  • [Bi(C8H18PS2)3]

  • Mr = 836.92

  • Monoclinic, P 21 /c

  • a = 13.954 (2) Å

  • b = 10.8719 (16) Å

  • c = 27.648 (3) Å

  • β = 119.312 (6)°

  • V = 3657.2 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 5.31 mm−1

  • T = 100 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.293, Tmax = 0.586

  • 18769 measured reflections

  • 6440 independent reflections

  • 5175 reflections with I > 2σ(I)

  • Rint = 0.056

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.072

  • S = 1.01

  • 6440 reflections

  • 319 parameters

  • H-atom parameters constrained

  • Δρmax = 1.50 e Å−3

  • Δρmin = −0.80 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the BI1/S1/P1/S2, BI1/S3/P2/S4 and BI1/S5/P3/S6 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C11—H11B⋯S4 0.98 2.8200 3.624 (8) 139.00
C17—H17A⋯S6i 0.99 2.8200 3.806 (6) 173.00
C3—H3CCg1 0.98 2.97 3.665 (8) 129.00
C14—H14⋯Cg2 1.00 2.74 3.248 (8) 112.00
C22—H22⋯Cg3 1.00 2.90 3.345 (6) 108.00
Symmetry code: (i) -x, -y, -z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information


Comment top

Organodithio-derivatives of phosphorus have several commercial applications, e.g. as additives to lubricant oils, petroleum additives, solvent extraction reagents for metals, flotation agents for mineral ores and as insecticides and pesticides in agriculture (Ebert et al., 1994). We report here the crystal structure of the title compound, Bi(C8H18PS2)3, (I).

In the structure of (I) a BiIII cation is present which is surrounded by three bis(2-methylpropyl)dithiophosphinate anions in a distorted octahedral coordination (Fig. 1). The Bi—S and S—P bond lengths are in the range of 2.7694 (18)—2.8391 (17) Å and 2.019 (2)—2.035 (2) Å, respectively. The S–Bi–S bond angles are in the range 72.90 (4)—163.04 (4)°. In comparison with (I), the crystal structure of bismuth(III) O,O'-di-isopropylphosphorodithioate (Lawton et al., 1974), (II), shows a similar coordination behaviour of the central BiIII cation. In structure (I) the four membered rings A (Bi1/S1/P1/S2), B (Bi1/S3/P2/S4) and C (Bi1/S5/P3/S6) are almost planar with r. m. s deviations from the plane of 0.066, 0.060 and 0.030 Å, respectively. The dihedral angles between A/B, A/C and B/C are 78.21 (3), 77.00 (4) and 75.78 (3)°, respectively. The molecules are stabilized due to hydrogen bonding interactions of the type C—H···S and additional C—H···π interactions (Table 1, Fig. 2).

Related literature top

For applications of organodithio derivatives of phosphorus compounds, see: Ebert et al. (1994). For a related structure, see: Lawton et al. (1974).

Experimental top

To an aqueous solution (50 ml) of bismuth(III) chloride (1.57 g, 5 mmol) in a round bottom flask, an aqueous solution (50 ml) of sodium diisobutyldithiophosphinate (3.825 g, 15 mmol) was added drop-wise, leading to the formation of a precipitate within an hour. After the completion of the reaction, the precipitate was filtered off, washed with distilled water and re-crystallized in acetone. Colorless, clear and shiny prisms of compound (I) were collected from the mother liquor within 7 days.

Refinement top

The H-atoms were positioned geometrically (C–H = 0.98–1.00 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and 1.2 for all other H-atoms.

Structure description top

Organodithio-derivatives of phosphorus have several commercial applications, e.g. as additives to lubricant oils, petroleum additives, solvent extraction reagents for metals, flotation agents for mineral ores and as insecticides and pesticides in agriculture (Ebert et al., 1994). We report here the crystal structure of the title compound, Bi(C8H18PS2)3, (I).

In the structure of (I) a BiIII cation is present which is surrounded by three bis(2-methylpropyl)dithiophosphinate anions in a distorted octahedral coordination (Fig. 1). The Bi—S and S—P bond lengths are in the range of 2.7694 (18)—2.8391 (17) Å and 2.019 (2)—2.035 (2) Å, respectively. The S–Bi–S bond angles are in the range 72.90 (4)—163.04 (4)°. In comparison with (I), the crystal structure of bismuth(III) O,O'-di-isopropylphosphorodithioate (Lawton et al., 1974), (II), shows a similar coordination behaviour of the central BiIII cation. In structure (I) the four membered rings A (Bi1/S1/P1/S2), B (Bi1/S3/P2/S4) and C (Bi1/S5/P3/S6) are almost planar with r. m. s deviations from the plane of 0.066, 0.060 and 0.030 Å, respectively. The dihedral angles between A/B, A/C and B/C are 78.21 (3), 77.00 (4) and 75.78 (3)°, respectively. The molecules are stabilized due to hydrogen bonding interactions of the type C—H···S and additional C—H···π interactions (Table 1, Fig. 2).

For applications of organodithio derivatives of phosphorus compounds, see: Ebert et al. (1994). For a related structure, see: Lawton et al. (1974).

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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) with the atom numbering scheme. Ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radius.
[Figure 2] Fig. 2. View of the partial packing of (I) which shows that molecules are interlinked through hydrogen bonding interactions.
Tris[bis(2-methylpropyl)dithiophosphinato]bismuth(III) top
Crystal data top
[Bi(C8H18PS2)3]F(000) = 1688
Mr = 836.92Dx = 1.520 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2649 reflections
a = 13.954 (2) Åθ = 2.0–26.4°
b = 10.8719 (16) ŵ = 5.31 mm1
c = 27.648 (3) ÅT = 100 K
β = 119.312 (6)°Prisms, colorless
V = 3657.2 (9) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6440 independent reflections
Radiation source: fine-focus sealed tube5175 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 7.82 pixels mm-1θmax = 25.0°, θmin = 2.1°
ω scansh = 916
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1212
Tmin = 0.293, Tmax = 0.586l = 3232
18769 measured reflections
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0247P)2]
where P = (Fo2 + 2Fc2)/3
6440 reflections(Δ/σ)max = 0.001
319 parametersΔρmax = 1.50 e Å3
0 restraintsΔρmin = 0.80 e Å3
Crystal data top
[Bi(C8H18PS2)3]V = 3657.2 (9) Å3
Mr = 836.92Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.954 (2) ŵ = 5.31 mm1
b = 10.8719 (16) ÅT = 100 K
c = 27.648 (3) Å0.30 × 0.20 × 0.10 mm
β = 119.312 (6)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6440 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
5175 reflections with I > 2σ(I)
Tmin = 0.293, Tmax = 0.586Rint = 0.056
18769 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.072H-atom parameters constrained
S = 1.01Δρmax = 1.50 e Å3
6440 reflectionsΔρmin = 0.80 e Å3
319 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Bi10.06995 (2)0.21172 (2)0.17013 (1)0.0163 (1)
S10.11857 (12)0.33737 (13)0.15017 (6)0.0224 (4)
S20.03418 (12)0.06325 (13)0.21195 (6)0.0227 (5)
S30.26521 (12)0.06889 (12)0.22085 (6)0.0206 (4)
S40.22263 (12)0.34033 (13)0.26537 (6)0.0226 (5)
S50.09638 (12)0.37496 (13)0.09744 (6)0.0211 (5)
S60.00195 (13)0.08630 (13)0.07039 (6)0.0246 (5)
P10.14233 (12)0.20298 (13)0.19409 (6)0.0178 (5)
P20.33382 (11)0.20960 (13)0.27465 (6)0.0177 (4)
P30.02840 (13)0.24188 (13)0.03923 (6)0.0201 (5)
C10.2816 (4)0.1437 (5)0.1584 (2)0.0205 (17)
C20.3138 (5)0.0524 (5)0.1105 (2)0.029 (2)
C30.3158 (6)0.1108 (7)0.0610 (3)0.053 (3)
C40.4249 (5)0.0039 (6)0.0953 (3)0.042 (2)
C50.1299 (5)0.2727 (5)0.2559 (2)0.0245 (19)
C60.1274 (5)0.1858 (5)0.3010 (2)0.0220 (19)
C70.1946 (5)0.2374 (6)0.3260 (3)0.039 (2)
C80.0108 (5)0.1609 (7)0.3458 (3)0.044 (3)
C90.4074 (4)0.1487 (5)0.3449 (2)0.0191 (17)
C100.3411 (5)0.0739 (5)0.3660 (2)0.0247 (17)
C110.2785 (6)0.1557 (7)0.3855 (3)0.054 (3)
C120.4183 (5)0.0086 (6)0.4133 (3)0.041 (2)
C130.4438 (4)0.2748 (5)0.2656 (2)0.0224 (17)
C140.4075 (5)0.3253 (5)0.2072 (3)0.030 (2)
C150.4928 (5)0.2942 (6)0.1895 (3)0.040 (2)
C160.3886 (6)0.4624 (6)0.2045 (3)0.049 (3)
C170.1147 (5)0.2134 (5)0.0084 (2)0.0269 (19)
C180.2382 (5)0.1969 (6)0.0471 (3)0.033 (2)
C190.2663 (6)0.0715 (6)0.0754 (3)0.047 (3)
C200.2997 (7)0.2164 (6)0.0149 (3)0.057 (3)
C210.1002 (5)0.2894 (5)0.0203 (2)0.0271 (19)
C220.1951 (5)0.3198 (5)0.0093 (2)0.0294 (19)
C230.3052 (6)0.2852 (6)0.0595 (3)0.051 (3)
C240.1956 (5)0.4512 (5)0.0067 (3)0.037 (2)
H1A0.295750.103470.186430.0243*
H1B0.332050.214970.143720.0243*
H20.257950.015080.123850.0354*
H3A0.366860.180520.048530.0794*
H3B0.339990.050210.030980.0794*
H3C0.241930.139830.070900.0794*
H4A0.481100.060630.081660.0634*
H4B0.421230.042690.128170.0634*
H4C0.443820.065960.066300.0634*
H5A0.061660.322290.273090.0293*
H5B0.192160.330330.244720.0293*
H60.160970.105640.282840.0263*
H7A0.192840.179680.353650.0582*
H7B0.270750.249440.296690.0582*
H7C0.163480.316460.343870.0582*
H8A0.023840.238210.364370.0661*
H8B0.030780.125140.329150.0661*
H8C0.011330.103300.372900.0661*
H9A0.467540.095640.347630.0227*
H9B0.442030.218680.370570.0227*
H100.287120.020940.335010.0295*
H11A0.236230.104470.397460.0812*
H11B0.228330.208970.354890.0812*
H11C0.330580.206460.416550.0812*
H12A0.472010.042120.443950.0613*
H12B0.456840.063680.400510.0613*
H12C0.376050.057410.426160.0613*
H13A0.478700.342220.292720.0270*
H13B0.500280.210650.274150.0270*
H140.336610.284820.180670.0356*
H15A0.466210.321810.151290.0597*
H15B0.504660.205020.191690.0597*
H15C0.562220.335690.214200.0597*
H16A0.456820.503750.230830.0730*
H16B0.331020.480690.214010.0730*
H16C0.365570.491800.166860.0730*
H17A0.086990.138440.014740.0327*
H17B0.104620.282680.016910.0327*
H180.262970.261450.076610.0392*
H19A0.243020.006730.047260.0699*
H19B0.228120.061290.096940.0699*
H19C0.345820.065970.100250.0699*
H20A0.378930.218480.040740.0851*
H20B0.276690.294400.005370.0851*
H20C0.282950.148660.011480.0851*
H21A0.085540.362870.036770.0325*
H21B0.124740.222960.048300.0325*
H220.185790.267660.022570.0348*
H23A0.364390.297630.050540.0764*
H23B0.303500.198590.068900.0764*
H23C0.318260.337050.091090.0764*
H24A0.126100.470200.040100.0546*
H24B0.256780.464690.014000.0546*
H24C0.204340.504920.023710.0546*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Bi10.0133 (1)0.0208 (1)0.0137 (1)0.0009 (1)0.0056 (1)0.0008 (1)
S10.0244 (8)0.0201 (7)0.0254 (8)0.0014 (7)0.0142 (7)0.0049 (6)
S20.0204 (8)0.0201 (8)0.0286 (8)0.0037 (7)0.0128 (7)0.0047 (6)
S30.0216 (8)0.0189 (7)0.0201 (8)0.0032 (6)0.0092 (7)0.0030 (6)
S40.0175 (8)0.0224 (8)0.0240 (8)0.0031 (7)0.0071 (7)0.0025 (6)
S50.0228 (8)0.0221 (8)0.0185 (8)0.0033 (7)0.0103 (7)0.0050 (6)
S60.0300 (9)0.0225 (8)0.0184 (8)0.0034 (7)0.0095 (7)0.0011 (6)
P10.0169 (8)0.0174 (8)0.0200 (8)0.0023 (7)0.0098 (6)0.0035 (6)
P20.0149 (7)0.0178 (8)0.0186 (7)0.0001 (7)0.0068 (6)0.0005 (7)
P30.0230 (8)0.0207 (8)0.0163 (8)0.0004 (7)0.0093 (7)0.0002 (6)
C10.016 (3)0.023 (3)0.024 (3)0.002 (3)0.011 (3)0.007 (3)
C20.021 (3)0.031 (4)0.031 (4)0.005 (3)0.009 (3)0.008 (3)
C30.051 (5)0.068 (5)0.040 (4)0.026 (4)0.023 (4)0.018 (4)
C40.031 (4)0.037 (4)0.042 (4)0.009 (3)0.005 (3)0.010 (3)
C50.036 (4)0.015 (3)0.030 (3)0.002 (3)0.022 (3)0.005 (3)
C60.031 (4)0.017 (3)0.021 (3)0.001 (3)0.015 (3)0.000 (2)
C70.036 (4)0.047 (4)0.031 (4)0.006 (3)0.015 (3)0.013 (3)
C80.040 (4)0.057 (5)0.030 (4)0.007 (4)0.013 (3)0.015 (3)
C90.016 (3)0.023 (3)0.016 (3)0.002 (3)0.006 (2)0.000 (2)
C100.022 (3)0.029 (3)0.020 (3)0.004 (3)0.008 (3)0.000 (3)
C110.058 (5)0.062 (5)0.065 (5)0.018 (4)0.047 (5)0.031 (4)
C120.044 (4)0.051 (4)0.039 (4)0.014 (4)0.029 (4)0.018 (3)
C130.018 (3)0.022 (3)0.028 (3)0.000 (3)0.012 (3)0.004 (3)
C140.019 (3)0.035 (4)0.031 (4)0.003 (3)0.008 (3)0.007 (3)
C150.035 (4)0.050 (4)0.037 (4)0.006 (4)0.020 (3)0.013 (3)
C160.038 (4)0.037 (4)0.071 (5)0.001 (4)0.026 (4)0.023 (4)
C170.040 (4)0.025 (3)0.023 (3)0.004 (3)0.021 (3)0.001 (3)
C180.032 (4)0.036 (4)0.045 (4)0.005 (3)0.030 (3)0.001 (3)
C190.044 (4)0.058 (5)0.046 (4)0.015 (4)0.028 (4)0.019 (4)
C200.070 (6)0.047 (5)0.082 (6)0.026 (5)0.060 (5)0.022 (4)
C210.035 (4)0.026 (3)0.012 (3)0.005 (3)0.005 (3)0.001 (3)
C220.023 (3)0.030 (4)0.028 (3)0.005 (3)0.007 (3)0.014 (3)
C230.038 (4)0.037 (4)0.051 (5)0.001 (4)0.001 (4)0.005 (4)
C240.033 (4)0.041 (4)0.035 (4)0.003 (3)0.016 (3)0.001 (3)
Geometric parameters (Å, º) top
Bi1—S12.7694 (18)C5—H5A0.9900
Bi1—S22.7747 (17)C5—H5B0.9900
Bi1—S32.8391 (17)C6—H61.0000
Bi1—S42.8169 (16)C7—H7A0.9800
Bi1—S52.8373 (16)C7—H7B0.9800
Bi1—S62.7859 (15)C7—H7C0.9800
S1—P12.028 (2)C8—H8A0.9800
S2—P12.025 (2)C8—H8B0.9800
S3—P22.019 (2)C8—H8C0.9800
S4—P22.026 (2)C9—H9A0.9900
S5—P32.022 (2)C9—H9B0.9900
S6—P32.035 (2)C10—H101.0000
P1—C11.813 (6)C11—H11A0.9800
P1—C51.799 (6)C11—H11B0.9800
P2—C91.820 (5)C11—H11C0.9800
P2—C131.816 (6)C12—H12A0.9800
P3—C171.810 (7)C12—H12B0.9800
P3—C211.818 (6)C12—H12C0.9800
C1—C21.536 (7)C13—H13A0.9900
C2—C31.497 (9)C13—H13B0.9900
C2—C41.522 (11)C14—H141.0000
C5—C61.551 (8)C15—H15A0.9800
C6—C71.519 (10)C15—H15B0.9800
C6—C81.511 (10)C15—H15C0.9800
C9—C101.545 (9)C16—H16A0.9800
C10—C111.519 (11)C16—H16B0.9800
C10—C121.515 (9)C16—H16C0.9800
C13—C141.538 (9)C17—H17A0.9900
C14—C151.530 (11)C17—H17B0.9900
C14—C161.509 (9)C18—H181.0000
C17—C181.530 (10)C19—H19A0.9800
C18—C191.525 (9)C19—H19B0.9800
C18—C201.524 (13)C19—H19C0.9800
C21—C221.533 (10)C20—H20A0.9800
C22—C231.530 (10)C20—H20B0.9800
C22—C241.497 (8)C20—H20C0.9800
C1—H1A0.9900C21—H21A0.9900
C1—H1B0.9900C21—H21B0.9900
C2—H21.0000C22—H221.0000
C3—H3A0.9800C23—H23A0.9800
C3—H3B0.9800C23—H23B0.9800
C3—H3C0.9800C23—H23C0.9800
C4—H4A0.9800C24—H24A0.9800
C4—H4B0.9800C24—H24B0.9800
C4—H4C0.9800C24—H24C0.9800
Bi1···H143.6700H7C···H5B2.5700
S1···S23.349 (2)H7C···H8A2.5400
S1···C33.616 (8)H8A···H5A2.3800
S2···S13.349 (2)H8A···H7C2.5400
S3···S43.361 (2)H8B···S22.9800
S4···C113.624 (8)H8B···C113.0400
S4···S33.361 (2)H8B···H5A2.5900
S5···C243.684 (8)H8B···H11A2.5600
S5···S63.360 (2)H8C···H7A2.4600
S6···S53.360 (2)H8C···S5i3.0300
S6···C193.681 (10)H9A···H12B2.3200
S1···H3C2.9500H9B···H11C2.4500
S2···H5Ai2.8800H9B···C23x3.0800
S2···H22.9900H9B···H23Ax2.5100
S2···H8B2.9800H10···S33.0600
S3···H103.0600H11A···C83.0800
S3···H142.9700H11A···H8B2.5600
S3···H5Bi3.1000H11A···H12C2.4500
S4···H16B2.9600H11B···S42.8200
S4···H1Aii3.1100H11C···H9B2.4500
S4···H11B2.8200H11C···H12A2.4900
S4···H6ii3.1200H11C···C20iv3.0700
S4···H4Bii3.1600H12A···H11C2.4900
S5···H143.1500H12B···H9A2.3200
S5···H8Cii3.0300H12B···H15Axi2.5000
S5···H182.9300H12C···H11A2.4500
S5···H24A2.9000H13A···H16A2.3700
S6···H19B2.9300H13B···H15B2.3100
S6···H222.9800H13B···H15C2.6000
S6···H17Aiii2.8200H13B···C16xi3.0200
P1···H3C3.0600H13B···H16Axi2.3500
P3···H19B3.1300H14···Bi13.6700
C3···S13.616 (8)H14···S32.9700
C11···S43.624 (8)H14···S53.1500
C19···S63.681 (10)H14···H182.5500
C24···S53.684 (8)H15A···H16C2.4800
C1···H63.0300H15A···H12Bv2.5000
C3···H223.0400H15B···H13B2.3100
C6···H1A3.0100H15C···H7Bxii2.5100
C8···H11A3.0800H15C···H13B2.6000
C11···H20Biv3.0800H15C···H16A2.5200
C11···H8B3.0400H16A···H13A2.3700
C16···H13Bv3.0200H16A···H15C2.5200
C19···H23Biii3.0000H16A···H13Bv2.3500
C20···H11Cvi3.0700H16B···S42.9600
C21···H7Avi3.0900H16C···H15A2.4800
C23···H9Bvii3.0800H17A···H19A2.4600
C24···H20Bviii2.9800H17A···S6iii2.8200
H1A···C63.0100H17B···H20B2.2700
H1A···H4B2.3300H17B···H21A2.5800
H1A···H62.3900H18···S52.9300
H1A···S4i3.1100H18···H142.5500
H1B···H3A2.4600H19A···H17A2.4600
H1B···H4A2.5700H19A···H20C2.4900
H2···S22.9900H19A···H23Biii2.3600
H3A···H1B2.4600H19B···S62.9300
H3A···H4A2.5500H19B···P33.1300
H3B···H4C2.4600H19C···H20A2.5300
H3B···H20Ciii2.4500H20A···H4Axii2.4200
H3C···S12.9500H20A···H19C2.5300
H3C···P13.0600H20B···H17B2.2700
H3C···H222.3100H20B···C24viii2.9800
H4A···H1B2.5700H20B···C11vi3.0800
H4A···H3A2.5500H20C···H19A2.4900
H4A···H20Aix2.4200H20C···H3Biii2.4500
H4B···H1A2.3300H21A···H17B2.5800
H4B···S4i3.1600H21A···H24C2.4200
H4C···H3B2.4600H21B···H23B2.2900
H5A···H8A2.3800H22···S62.9800
H5A···H8B2.5900H22···C33.0400
H5A···S2ii2.8800H22···H3C2.3100
H5B···H7B2.3600H23A···H24B2.4700
H5B···H7C2.5700H23A···H9Bvii2.5100
H5B···S3ii3.1000H23B···H21B2.2900
H6···C13.0300H23B···C19iii3.0000
H6···H1A2.3900H23B···H19Aiii2.3600
H6···S4i3.1200H23C···H24C2.5400
H7A···H8C2.4600H24A···S52.9000
H7A···C21iv3.0900H24B···H23A2.4700
H7B···H5B2.3600H24C···H21A2.4200
H7B···H15Cix2.5100H24C···H23C2.5400
S1—Bi1—S274.33 (5)C6—C7—H7B110.00
S1—Bi1—S3163.04 (5)C6—C7—H7C109.00
S1—Bi1—S498.71 (5)H7A—C7—H7B109.00
S1—Bi1—S589.46 (5)H7A—C7—H7C109.00
S1—Bi1—S6101.39 (5)H7B—C7—H7C109.00
S2—Bi1—S392.74 (5)C6—C8—H8A109.00
S2—Bi1—S4102.12 (5)C6—C8—H8B109.00
S2—Bi1—S5159.27 (5)C6—C8—H8C109.00
S2—Bi1—S696.86 (5)H8A—C8—H8B109.00
S3—Bi1—S472.90 (4)H8A—C8—H8C110.00
S3—Bi1—S5105.42 (5)H8B—C8—H8C109.00
S3—Bi1—S690.84 (5)P2—C9—H9A108.00
S4—Bi1—S592.90 (4)P2—C9—H9B108.00
S4—Bi1—S6155.41 (6)C10—C9—H9A108.00
S5—Bi1—S673.37 (4)C10—C9—H9B108.00
Bi1—S1—P186.74 (7)H9A—C9—H9B107.00
Bi1—S2—P186.66 (7)C9—C10—H10109.00
Bi1—S3—P286.78 (7)C11—C10—H10109.00
Bi1—S4—P287.25 (6)C12—C10—H10109.00
Bi1—S5—P386.74 (7)C10—C11—H11A109.00
Bi1—S6—P387.91 (6)C10—C11—H11B109.00
S1—P1—S2111.45 (11)C10—C11—H11C109.00
S1—P1—C1112.09 (18)H11A—C11—H11B110.00
S1—P1—C5107.3 (2)H11A—C11—H11C110.00
S2—P1—C1109.78 (19)H11B—C11—H11C109.00
S2—P1—C5111.8 (2)C10—C12—H12A109.00
C1—P1—C5104.2 (3)C10—C12—H12B110.00
S3—P2—S4112.39 (10)C10—C12—H12C110.00
S3—P2—C9109.08 (19)H12A—C12—H12B109.00
S3—P2—C13108.80 (19)H12A—C12—H12C109.00
S4—P2—C9112.8 (2)H12B—C12—H12C110.00
S4—P2—C13110.81 (19)P2—C13—H13A109.00
C9—P2—C13102.5 (3)P2—C13—H13B109.00
S5—P3—S6111.82 (9)C14—C13—H13A109.00
S5—P3—C17109.6 (2)C14—C13—H13B108.00
S5—P3—C21112.82 (19)H13A—C13—H13B108.00
S6—P3—C17112.43 (19)C13—C14—H14108.00
S6—P3—C21107.6 (2)C15—C14—H14108.00
C17—P3—C21102.2 (3)C16—C14—H14108.00
P1—C1—C2118.8 (5)C14—C15—H15A110.00
C1—C2—C3112.4 (5)C14—C15—H15B109.00
C1—C2—C4109.1 (6)C14—C15—H15C109.00
C3—C2—C4111.0 (5)H15A—C15—H15B109.00
P1—C5—C6117.4 (4)H15A—C15—H15C109.00
C5—C6—C7111.4 (5)H15B—C15—H15C109.00
C5—C6—C8111.1 (6)C14—C16—H16A109.00
C7—C6—C8110.5 (5)C14—C16—H16B109.00
P2—C9—C10117.7 (4)C14—C16—H16C109.00
C9—C10—C11112.4 (5)H16A—C16—H16B109.00
C9—C10—C12109.5 (6)H16A—C16—H16C109.00
C11—C10—C12109.3 (5)H16B—C16—H16C109.00
P2—C13—C14114.7 (4)P3—C17—H17A108.00
C13—C14—C15110.4 (6)P3—C17—H17B108.00
C13—C14—C16111.4 (5)C18—C17—H17A108.00
C15—C14—C16110.3 (6)C18—C17—H17B108.00
P3—C17—C18118.2 (4)H17A—C17—H17B107.00
C17—C18—C19112.5 (6)C17—C18—H18108.00
C17—C18—C20109.8 (6)C19—C18—H18108.00
C19—C18—C20110.3 (6)C20—C18—H18108.00
P3—C21—C22116.6 (4)C18—C19—H19A109.00
C21—C22—C23110.4 (5)C18—C19—H19B109.00
C21—C22—C24113.2 (6)C18—C19—H19C109.00
C23—C22—C24110.8 (6)H19A—C19—H19B109.00
P1—C1—H1A108.00H19A—C19—H19C110.00
P1—C1—H1B108.00H19B—C19—H19C109.00
C2—C1—H1A108.00C18—C20—H20A110.00
C2—C1—H1B108.00C18—C20—H20B110.00
H1A—C1—H1B107.00C18—C20—H20C109.00
C1—C2—H2108.00H20A—C20—H20B110.00
C3—C2—H2108.00H20A—C20—H20C109.00
C4—C2—H2108.00H20B—C20—H20C109.00
C2—C3—H3A110.00P3—C21—H21A108.00
C2—C3—H3B109.00P3—C21—H21B108.00
C2—C3—H3C110.00C22—C21—H21A108.00
H3A—C3—H3B109.00C22—C21—H21B108.00
H3A—C3—H3C109.00H21A—C21—H21B107.00
H3B—C3—H3C109.00C21—C22—H22107.00
C2—C4—H4A109.00C23—C22—H22107.00
C2—C4—H4B109.00C24—C22—H22107.00
C2—C4—H4C109.00C22—C23—H23A109.00
H4A—C4—H4B109.00C22—C23—H23B109.00
H4A—C4—H4C109.00C22—C23—H23C109.00
H4B—C4—H4C109.00H23A—C23—H23B109.00
P1—C5—H5A108.00H23A—C23—H23C110.00
P1—C5—H5B108.00H23B—C23—H23C110.00
C6—C5—H5A108.00C22—C24—H24A110.00
C6—C5—H5B108.00C22—C24—H24B110.00
H5A—C5—H5B107.00C22—C24—H24C109.00
C5—C6—H6108.00H24A—C24—H24B110.00
C7—C6—H6108.00H24A—C24—H24C109.00
C8—C6—H6108.00H24B—C24—H24C109.00
C6—C7—H7A109.00
S2—Bi1—S1—P15.75 (6)Bi1—S4—P2—C9131.4 (2)
S4—Bi1—S1—P194.48 (7)Bi1—S4—P2—C13114.39 (18)
S5—Bi1—S1—P1172.68 (6)Bi1—S5—P3—S63.68 (11)
S6—Bi1—S1—P199.77 (7)Bi1—S5—P3—C17129.07 (19)
S1—Bi1—S2—P15.77 (6)Bi1—S5—P3—C21117.7 (3)
S3—Bi1—S2—P1163.10 (6)Bi1—S6—P3—S53.75 (11)
S4—Bi1—S2—P190.01 (7)Bi1—S6—P3—C17127.6 (2)
S5—Bi1—S2—P145.50 (15)Bi1—S6—P3—C21120.7 (2)
S6—Bi1—S2—P1105.72 (7)S1—P1—C1—C278.1 (4)
S2—Bi1—S3—P2107.07 (7)S2—P1—C1—C246.3 (4)
S4—Bi1—S3—P25.23 (7)C5—P1—C1—C2166.2 (4)
S5—Bi1—S3—P283.06 (7)S1—P1—C5—C6171.1 (5)
S6—Bi1—S3—P2156.02 (7)S2—P1—C5—C648.6 (6)
S1—Bi1—S4—P2170.07 (7)C1—P1—C5—C669.9 (6)
S2—Bi1—S4—P294.35 (7)S3—P2—C9—C1059.2 (4)
S3—Bi1—S4—P25.21 (7)S4—P2—C9—C1066.4 (4)
S5—Bi1—S4—P2100.04 (7)C13—P2—C9—C10174.4 (4)
S6—Bi1—S4—P245.36 (13)S3—P2—C13—C1459.9 (4)
S1—Bi1—S5—P399.46 (8)S4—P2—C13—C1464.2 (4)
S2—Bi1—S5—P361.48 (15)C9—P2—C13—C14175.3 (4)
S3—Bi1—S5—P388.79 (8)S5—P3—C17—C1847.6 (5)
S4—Bi1—S5—P3161.85 (8)S6—P3—C17—C1877.5 (5)
S6—Bi1—S5—P32.61 (8)C21—P3—C17—C18167.5 (4)
S1—Bi1—S6—P383.38 (8)S5—P3—C21—C2263.2 (5)
S2—Bi1—S6—P3158.71 (8)S6—P3—C21—C2260.6 (4)
S3—Bi1—S6—P3108.44 (8)C17—P3—C21—C22179.1 (4)
S4—Bi1—S6—P360.85 (13)P1—C1—C2—C368.1 (7)
S5—Bi1—S6—P32.59 (8)P1—C1—C2—C4168.4 (4)
Bi1—S1—P1—S28.17 (9)P1—C5—C6—C7139.3 (5)
Bi1—S1—P1—C1131.7 (2)P1—C5—C6—C897.1 (6)
Bi1—S1—P1—C5114.5 (2)P2—C9—C10—C1180.6 (5)
Bi1—S2—P1—S18.16 (9)P2—C9—C10—C12157.8 (4)
Bi1—S2—P1—C1132.95 (19)P2—C13—C14—C15140.2 (5)
Bi1—S2—P1—C5111.9 (2)P2—C13—C14—C1696.9 (6)
Bi1—S3—P2—S47.52 (9)P3—C17—C18—C1975.4 (6)
Bi1—S3—P2—C9133.4 (2)P3—C17—C18—C20161.4 (4)
Bi1—S3—P2—C13115.58 (19)P3—C21—C22—C23147.1 (4)
Bi1—S4—P2—S37.58 (9)P3—C21—C22—C2488.1 (5)
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+1/2, z+1/2; (iii) x, y, z; (iv) x, y+1/2, z+1/2; (v) x+1, y+1/2, z+1/2; (vi) x, y+1/2, z1/2; (vii) x1, y+1/2, z1/2; (viii) x, y+1, z; (ix) x1, y, z; (x) x+1, y+1/2, z+1/2; (xi) x+1, y1/2, z+1/2; (xii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the BI1/S1/P1/S2, BI1/S3/P2/S4 and BI1/S5/P3/S6 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11B···S40.982.82003.624 (8)139.00
C17—H17A···S6iii0.992.82003.806 (6)173.00
C3—H3C···Cg10.982.973.665 (8)129.00
C14—H14···Cg21.002.743.248 (8)112.00
C22—H22···Cg31.002.903.345 (6)108.00
Symmetry code: (iii) x, y, z.

Experimental details

Crystal data
Chemical formula[Bi(C8H18PS2)3]
Mr836.92
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)13.954 (2), 10.8719 (16), 27.648 (3)
β (°) 119.312 (6)
V3)3657.2 (9)
Z4
Radiation typeMo Kα
µ (mm1)5.31
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.293, 0.586
No. of measured, independent and
observed [I > 2σ(I)] reflections
18769, 6440, 5175
Rint0.056
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.072, 1.01
No. of reflections6440
No. of parameters319
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.50, 0.80

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the BI1/S1/P1/S2, BI1/S3/P2/S4 and BI1/S5/P3/S6 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11B···S40.982.82003.624 (8)139.00
C17—H17A···S6i0.992.82003.806 (6)173.00
C3—H3C···Cg10.982.973.665 (8)129.00
C14—H14···Cg21.002.743.248 (8)112.00
C22—H22···Cg31.002.903.345 (6)108.00
Symmetry code: (i) x, y, z.
 

Acknowledgements

HAS gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a scholarship under the Indigenous PhD Program (PIN 042-160410-PS2-117).

References

First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationEbert, K., Breunig, H., Silvestru, C., Stefan, I. & Haiduc, I. (1994). Inorg. Chem. 33, 1695–1699.  CSD CrossRef CAS Web of Science Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationLawton, S. L., Fuhrmeister, C. J., Haas, R. G., Jarman Jr, C. S. & Lohmeyer, F. G. (1974). Inorg. Chem. 13, 135–143.  CSD CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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