Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100002390/qb0189sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100002390/qb0189Isup2.hkl |
CCDC reference: 143330
The title compound, trans-2,4-di-tert-butyl-1,3-dithia-2,4-diphosphetane-2,4-dithione, was prepared during the reaction of tert-butyllithium with pyridine (py) stabilized dithiometaphosphoryl chloride py→ PS2Cl. Slow dropping of one equivalent of tert-butyllithium into a suspension of py→ PS2Cl in benzene at 323 K, filtration, evaporation at high vacuum, and recrystallization from toluene produced crystals suitable for X-ray analysis.
Data collection: STADI4-1.06 (Stoe & Cie, 1997); cell refinement: STADI4-1.06; data reduction: X-RED1.07 (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
C8H18P2S4 | F(000) = 320 |
Mr = 304.40 | Dx = 1.422 Mg m−3 |
Monoclinic, C2/m | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7313 (8) Å | Cell parameters from 62 reflections |
b = 9.2898 (11) Å | θ = 13.0–17.1° |
c = 8.115 (1) Å | µ = 0.86 mm−1 |
β = 104.252 (8)° | T = 180 K |
V = 711.03 (13) Å3 | Square plate, colorless |
Z = 2 | 0.57 × 0.57 × 0.26 mm |
Stoe Stadi-4 diffractometer | 846 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.038 |
Planar graphite monochromator | θmax = 27.6°, θmin = 2.6° |
2θ/ω scan, ratio = 1.0, width(ω) = 1.55–1.7° | h = −12→12 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→12 |
Tmin = 0.640, Tmax = 0.808 | l = −10→10 |
3495 measured reflections | 3 standard reflections every 120 min |
876 independent reflections | intensity decay: 4.5% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.025 | All H-atom parameters refined |
wR(F2) = 0.064 | w = 1/[σ2(Fo2) + (0.0387P)2 + 0.2726P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max = 0.007 |
876 reflections | Δρmax = 0.56 e Å−3 |
59 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.038 (3) |
C8H18P2S4 | V = 711.03 (13) Å3 |
Mr = 304.40 | Z = 2 |
Monoclinic, C2/m | Mo Kα radiation |
a = 9.7313 (8) Å | µ = 0.86 mm−1 |
b = 9.2898 (11) Å | T = 180 K |
c = 8.115 (1) Å | 0.57 × 0.57 × 0.26 mm |
β = 104.252 (8)° |
Stoe Stadi-4 diffractometer | 846 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.038 |
Tmin = 0.640, Tmax = 0.808 | 3 standard reflections every 120 min |
3495 measured reflections | intensity decay: 4.5% |
876 independent reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.064 | All H-atom parameters refined |
S = 1.15 | Δρmax = 0.56 e Å−3 |
876 reflections | Δρmin = −0.42 e Å−3 |
59 parameters |
Experimental. Recrystallized from toluene. During data collection the crystal was in cold N2 gas of a cryostream cooler (Oxford Cryosystems, 1992). |
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 | ||
C1 | 0.26900 (17) | 0.0000 | 0.7169 (2) | 0.0213 (3) | |
C2 | 0.3839 (2) | 0.0000 | 0.6188 (2) | 0.0316 (4) | |
H2A | 0.340 (3) | 0.0000 | 0.498 (3) | 0.041 (7)* | |
H2B | 0.4395 (19) | 0.087 (2) | 0.642 (2) | 0.037 (4)* | |
C3 | 0.17746 (16) | 0.13571 (17) | 0.67561 (18) | 0.0340 (3) | |
H3A | 0.140 (2) | 0.135 (2) | 0.556 (2) | 0.046 (5)* | |
H3B | 0.2344 (19) | 0.220 (2) | 0.710 (2) | 0.046 (5)* | |
H3C | 0.103 (2) | 0.132 (2) | 0.733 (3) | 0.050 (5)* | |
P1 | 0.34693 (4) | 0.0000 | 0.94995 (5) | 0.01647 (16) | |
S2 | 0.5000 | 0.16765 (4) | 1.0000 | 0.01934 (16) | |
S3 | 0.20793 (4) | 0.0000 | 1.08369 (5) | 0.02503 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0191 (7) | 0.0244 (8) | 0.0181 (7) | 0.000 | 0.0000 (5) | 0.000 |
C2 | 0.0287 (9) | 0.0455 (12) | 0.0207 (8) | 0.000 | 0.0060 (7) | 0.000 |
C3 | 0.0358 (7) | 0.0326 (7) | 0.0284 (6) | 0.0107 (6) | −0.0019 (5) | 0.0039 (5) |
P1 | 0.0127 (2) | 0.0172 (2) | 0.0189 (2) | 0.000 | 0.00270 (15) | 0.000 |
S2 | 0.0158 (2) | 0.0152 (2) | 0.0258 (2) | 0.000 | 0.00289 (15) | 0.000 |
S3 | 0.0200 (2) | 0.0286 (3) | 0.0291 (3) | 0.000 | 0.01107 (17) | 0.000 |
C1—C2 | 1.524 (3) | C3—H3B | 0.96 (2) |
C1—C3i | 1.5324 (18) | C3—H3C | 0.96 (2) |
C1—C3 | 1.5324 (18) | P1—S3 | 1.9314 (6) |
C1—P1 | 1.8561 (16) | P1—S2 | 2.1240 (4) |
C2—H2A | 0.96 (3) | P1—S2ii | 2.1240 (4) |
C2—H2B | 0.962 (18) | S2—P1ii | 2.1240 (4) |
C3—H3A | 0.951 (18) | ||
C2—C1—C3i | 110.33 (10) | H3A—C3—H3B | 110.4 (17) |
C2—C1—C3 | 110.33 (10) | C1—C3—H3C | 109.6 (13) |
C3i—C1—C3 | 110.71 (16) | H3A—C3—H3C | 110.8 (16) |
C2—C1—P1 | 111.35 (11) | H3B—C3—H3C | 109.7 (17) |
C3i—C1—P1 | 107.01 (9) | C1—P1—S3 | 113.92 (6) |
C3—C1—P1 | 107.01 (9) | C1—P1—S2 | 106.63 (4) |
C1—C2—H2A | 109.3 (16) | S3—P1—S2 | 116.601 (16) |
C1—C2—H2B | 110.3 (10) | C1—P1—S2ii | 106.63 (4) |
H2A—C2—H2B | 106.6 (12) | S3—P1—S2ii | 116.601 (16) |
C1—C3—H3A | 106.1 (13) | S2—P1—S2ii | 94.32 (2) |
C1—C3—H3B | 110.2 (11) | P1—S2—P1ii | 85.68 (2) |
C2—C1—P1—S3 | 180.0 | C2—C1—P1—S2ii | −49.929 (18) |
C3i—C1—P1—S3 | −59.36 (10) | C3i—C1—P1—S2ii | 70.71 (11) |
C3—C1—P1—S3 | 59.36 (10) | C3—C1—P1—S2ii | −170.57 (9) |
C2—C1—P1—S2 | 49.929 (18) | C1—P1—S2—P1ii | −108.79 (5) |
C3i—C1—P1—S2 | 170.57 (9) | S3—P1—S2—P1ii | 122.68 (3) |
C3—C1—P1—S2 | −70.71 (11) | S2ii—P1—S2—P1ii | 0.0 |
Symmetry codes: (i) x, −y, z; (ii) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C8H18P2S4 |
Mr | 304.40 |
Crystal system, space group | Monoclinic, C2/m |
Temperature (K) | 180 |
a, b, c (Å) | 9.7313 (8), 9.2898 (11), 8.115 (1) |
β (°) | 104.252 (8) |
V (Å3) | 711.03 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.86 |
Crystal size (mm) | 0.57 × 0.57 × 0.26 |
Data collection | |
Diffractometer | Stoe Stadi-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.640, 0.808 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3495, 876, 846 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.064, 1.15 |
No. of reflections | 876 |
No. of parameters | 59 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.56, −0.42 |
Computer programs: STADI4-1.06 (Stoe & Cie, 1997), STADI4-1.06, X-RED1.07 (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXL97.