1,1,2,2-Tetra­phenyl-1λ5-diphosphane 1-sulfide

Aluri, B.R.; Peitz, S.; Wöhl, A.; Peulecke, N.; Müller, B.H.; Spannenberg, A.; Rosenthal, U.

doi:10.1107/S1600536809002955

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o404

doi:10.1107/S1600536809002955

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1,1,2,2-Tetraphenyl-1λ⁵-diphosphane 1-sulfide

Bhaskar R. Aluri,^a ^* Stephan Peitz,^a Anina Wöhl,^b Normen Peulecke,^a Bernd H. Müller,^a Anke Spannenberg ^a and Uwe Rosenthal ^a

^aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany, and ^bLinde AG, Linde Engineering Division, Dr.-Carl-von-Linde-Strasse 6–14, 82049 Pullach, Germany
^*Correspondence e-mail: bhaskar-reddy.aluri@catalysis.de

(Received 20 January 2009; accepted 23 January 2009; online 28 January 2009)

In the title molecule, C₂₄H₂₀P₂S, the P—P bond length is 2.2263 (5) Å. The two phenyl rings attached to the three- and five-coordinated P atoms, respectively, form dihedral angles of 56.22 (5) and 71.74 (5)°.

Related literature

For the literature on related compounds, see: Bhattacharyya et al. (1996 ); Gruber et al. (1990 ); Jones et al. (2002 ).

Experimental

Crystal data

C₂₄H₂₀P₂S
M_r = 402.40
Monoclinic, P 2₁ /c
a = 9.32670 (19) Å
b = 13.6496 (4) Å
c = 16.0484 (4) Å
β = 91.7298 (17)°
V = 2042.12 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 200 (2) K
0.45 × 0.30 × 0.28 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ) T_min = 0.892, T_max = 0.961
38972 measured reflections
5499 independent reflections
4493 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.096
S = 1.08
5499 reflections
244 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002955/cv2512sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002955/cv2512Isup2.hkl

checkCIF report

Comment top

Earlier, Gruber et al. (1990) reported that the only phosphorus-containing product formed from the reaction between Ph₂PCl and thiourea was tetraphenyldiphosphane monosulfide. Bhattacharyya et al. (1996) reported this monosulfide formed as the by-product from the same reaction using different reaction conditions. In the present publication, we report the formation of tetraphenyldiphosphane monosulfide, which was observed as a major by-product in the reaction of Ph₂P(S)CH₂N(Li)Ph and ClPPh₂. Its molecular structure (Fig. 1) shows the bond lengths and bond angles are within the normal ranges and are in accordance with the corresponding values in tetramethyldiphosphane monosulfide (Gruber et al., 1990). The molecular structure of pentacarbonyl(tetraphenyldiphosphinomonosulfide-P)chromium(0) was reported earlier by Jones et al. (2002).

Related literature top

For the crystal structures of related compounds, see: Bhattacharyya et al. (1996); Gruber et al. (1990); Jones et al. (2002).

Experimental top

BuLi (0.77 ml, 1.94 mmol, 2.5 M in n-hexane) was added dropwise to a solution of Ph₂P(S)CH₂N(H)Ph (660 mg, 2.03 mmol) in THF (5 ml) at -78°C and this reaction mixture was stirred for 4 h while slowly warming up to -40°C. The resultant yellow solution was added to ClPPh₂ (0.38 ml, 2.03 mmol) at 0°C in small portions via a cannula over a period of 20 min and followed stirring at room temperature overnight. The major part of THF was removed from the reaction mixture and over-layered with n-hexane to get single crystals of the title compound, which were suitable for X-ray analysis. ³¹P NMR (THF-d₈): -14.11 (d, ¹J = 247.3 Hz), 44.11 (d, ¹J = 247.3 Hz).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme and 30% probability displacement ellipsoids.

1,1,2,2-Tetraphenyl-1λ⁵-diphosphane 1-sulfide top

Crystal data top

C₂₄H₂₀P₂S	F(000) = 840
M_r = 402.40	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 32981 reflections
a = 9.32670 (19) Å	θ = 2.0–29.6°
b = 13.6496 (4) Å	µ = 0.32 mm⁻¹
c = 16.0484 (4) Å	T = 200 K
β = 91.7298 (17)°	Prism, colourless
V = 2042.12 (9) Å³	0.45 × 0.30 × 0.28 mm
Z = 4

Data collection top

Stoe IPDS II diffractometer	5499 independent reflections
Radiation source: fine-focus sealed tube	4493 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
rotation method scans	θ_max = 29.1°, θ_min = 2.0°
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	h = −12→12
T_min = 0.892, T_max = 0.961	k = −18→18
38972 measured reflections	l = −21→21

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0564P)² + 0.1948P] where P = (F_o² + 2F_c²)/3
5499 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.29 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₄H₂₀P₂S	V = 2042.12 (9) Å³
M_r = 402.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.32670 (19) Å	µ = 0.32 mm⁻¹
b = 13.6496 (4) Å	T = 200 K
c = 16.0484 (4) Å	0.45 × 0.30 × 0.28 mm
β = 91.7298 (17)°

Data collection top

Stoe IPDS II diffractometer	5499 independent reflections
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	4493 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.961	R_int = 0.027
38972 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.096	H-atom parameters constrained
S = 1.08	Δρ_max = 0.29 e Å⁻³
5499 reflections	Δρ_min = −0.28 e Å⁻³
244 parameters

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	U_iso*/U_eq
C1	0.58305 (14)	0.77663 (9)	−0.01356 (8)	0.0323 (3)
C2	0.58628 (15)	0.78402 (11)	−0.10028 (8)	0.0380 (3)
H2A	0.5640	0.7283	−0.1337	0.046*
C3	0.62169 (16)	0.87176 (12)	−0.13813 (10)	0.0450 (3)
H3A	0.6232	0.8761	−0.1972	0.054*
C4	0.65480 (16)	0.95274 (11)	−0.08978 (11)	0.0469 (3)
H4A	0.6797	1.0128	−0.1156	0.056*
C5	0.65188 (16)	0.94677 (11)	−0.00372 (10)	0.0439 (3)
H5A	0.6751	1.0026	0.0293	0.053*
C6	0.61519 (15)	0.85951 (10)	0.03445 (9)	0.0376 (3)
H6A	0.6119	0.8561	0.0935	0.045*
C7	0.66830 (14)	0.62119 (9)	0.10362 (7)	0.0309 (2)
C8	0.78956 (15)	0.67684 (11)	0.12330 (9)	0.0399 (3)
H8A	0.7999	0.7401	0.0996	0.048*
C9	0.89570 (16)	0.64037 (12)	0.17754 (10)	0.0455 (3)
H9A	0.9782	0.6789	0.1906	0.055*
C10	0.88200 (16)	0.54883 (12)	0.21250 (9)	0.0436 (3)
H10A	0.9544	0.5244	0.2499	0.052*
C11	0.76235 (17)	0.49268 (11)	0.19287 (9)	0.0420 (3)
H11A	0.7528	0.4294	0.2167	0.050*
C12	0.65601 (15)	0.52821 (10)	0.13849 (8)	0.0360 (3)
H12A	0.5745	0.4889	0.1250	0.043*
C13	0.22346 (14)	0.75419 (10)	0.03664 (9)	0.0352 (3)
C14	0.21864 (17)	0.73376 (12)	−0.04835 (10)	0.0461 (3)
H14A	0.2841	0.6882	−0.0708	0.055*
C15	0.11782 (19)	0.78017 (15)	−0.10032 (11)	0.0589 (5)
H15A	0.1161	0.7675	−0.1586	0.071*
C16	0.02074 (18)	0.84419 (13)	−0.06782 (10)	0.0609 (5)
H16A	−0.0496	0.8743	−0.1034	0.073*
C17	0.02482 (17)	0.86493 (12)	0.01602 (12)	0.0557 (4)
H17A	−0.0422	0.9097	0.0380	0.067*
C18	0.12649 (16)	0.82073 (11)	0.06868 (11)	0.0430 (3)
H18A	0.1298	0.8359	0.1265	0.052*
C19	0.28040 (15)	0.57847 (10)	0.13544 (9)	0.0379 (3)
C20	0.21178 (18)	0.51924 (11)	0.07596 (10)	0.0459 (3)
H20A	0.1989	0.5421	0.0203	0.055*
C21	0.1620 (2)	0.42703 (13)	0.09741 (13)	0.0589 (5)
H21A	0.1140	0.3873	0.0568	0.071*
C22	0.1824 (2)	0.39341 (13)	0.17769 (15)	0.0642 (5)
H22A	0.1500	0.3299	0.1922	0.077*
C23	0.2495 (2)	0.45130 (16)	0.23683 (14)	0.0675 (6)
H23A	0.2627	0.4275	0.2922	0.081*
C24	0.29853 (18)	0.54423 (14)	0.21697 (11)	0.0532 (4)
H24A	0.3439	0.5841	0.2585	0.064*
P1	0.53134 (3)	0.65612 (2)	0.024981 (19)	0.03019 (9)
P2	0.35427 (4)	0.69731 (2)	0.10811 (2)	0.03240 (9)
S1	0.39983 (5)	0.77769 (3)	0.20569 (2)	0.04904 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0296 (6)	0.0325 (6)	0.0344 (6)	0.0026 (5)	−0.0032 (5)	0.0022 (5)
C2	0.0367 (7)	0.0421 (7)	0.0350 (6)	0.0007 (6)	−0.0036 (5)	0.0036 (5)
C3	0.0396 (8)	0.0531 (8)	0.0423 (7)	0.0007 (6)	0.0002 (6)	0.0132 (6)
C4	0.0374 (7)	0.0414 (8)	0.0619 (9)	0.0012 (6)	0.0019 (6)	0.0156 (7)
C5	0.0371 (7)	0.0336 (7)	0.0608 (9)	0.0017 (6)	−0.0018 (6)	−0.0012 (6)
C6	0.0363 (7)	0.0359 (7)	0.0404 (7)	0.0015 (5)	−0.0020 (5)	−0.0015 (5)
C7	0.0305 (6)	0.0328 (6)	0.0294 (5)	0.0062 (5)	−0.0001 (4)	−0.0012 (4)
C8	0.0347 (7)	0.0404 (7)	0.0441 (7)	−0.0002 (5)	−0.0050 (6)	0.0058 (6)
C9	0.0317 (7)	0.0548 (9)	0.0494 (8)	0.0009 (6)	−0.0065 (6)	0.0038 (7)
C10	0.0391 (7)	0.0533 (8)	0.0383 (7)	0.0160 (6)	−0.0034 (6)	0.0020 (6)
C11	0.0511 (8)	0.0361 (7)	0.0390 (7)	0.0121 (6)	0.0018 (6)	0.0043 (5)
C12	0.0392 (7)	0.0312 (6)	0.0373 (6)	0.0045 (5)	−0.0005 (5)	−0.0015 (5)
C13	0.0304 (6)	0.0321 (6)	0.0430 (7)	0.0011 (5)	−0.0030 (5)	0.0059 (5)
C14	0.0389 (7)	0.0547 (9)	0.0438 (7)	0.0065 (7)	−0.0107 (6)	0.0024 (6)
C15	0.0479 (9)	0.0735 (12)	0.0542 (9)	0.0031 (8)	−0.0182 (8)	0.0125 (8)
C16	0.0405 (8)	0.0593 (10)	0.0816 (13)	0.0032 (8)	−0.0181 (8)	0.0254 (9)
C17	0.0359 (8)	0.0426 (8)	0.0887 (13)	0.0083 (6)	0.0001 (8)	0.0139 (8)
C18	0.0343 (7)	0.0352 (7)	0.0595 (9)	0.0035 (5)	0.0032 (6)	0.0068 (6)
C19	0.0321 (6)	0.0387 (7)	0.0432 (7)	0.0083 (5)	0.0062 (5)	0.0076 (5)
C20	0.0526 (9)	0.0380 (7)	0.0481 (8)	0.0001 (6)	0.0162 (7)	−0.0033 (6)
C21	0.0642 (11)	0.0407 (8)	0.0733 (11)	−0.0032 (8)	0.0278 (9)	−0.0076 (8)
C22	0.0558 (11)	0.0419 (9)	0.0963 (15)	0.0086 (8)	0.0248 (10)	0.0192 (9)
C23	0.0510 (10)	0.0739 (13)	0.0776 (12)	0.0079 (9)	0.0020 (9)	0.0428 (11)
C24	0.0423 (8)	0.0632 (10)	0.0538 (9)	0.0029 (7)	−0.0049 (7)	0.0224 (8)
P1	0.03128 (16)	0.03040 (16)	0.02864 (15)	0.00166 (12)	−0.00294 (12)	−0.00140 (11)
P2	0.03193 (17)	0.03396 (17)	0.03117 (16)	0.00544 (13)	−0.00136 (12)	0.00023 (12)
S1	0.0586 (2)	0.0524 (2)	0.03591 (18)	0.00869 (18)	−0.00217 (16)	−0.01034 (15)

Geometric parameters (Å, º) top

C1—C6	1.3962 (18)	C13—C14	1.392 (2)
C1—C2	1.3966 (18)	C13—P2	1.8228 (13)
C1—P1	1.8273 (13)	C14—C15	1.391 (2)
C2—C3	1.387 (2)	C14—H14A	0.9500
C2—H2A	0.9500	C15—C16	1.3727 (19)
C3—C4	1.380 (2)	C15—H15A	0.9500
C3—H3A	0.9500	C16—C17	1.3743 (19)
C4—C5	1.385 (2)	C16—H16A	0.9500
C4—H4A	0.9500	C17—C18	1.389 (2)
C5—C6	1.387 (2)	C17—H17A	0.9500
C5—H5A	0.9500	C18—H18A	0.9500
C6—H6A	0.9500	C19—C20	1.392 (2)
C7—C8	1.3907 (19)	C19—C24	1.395 (2)
C7—C12	1.3931 (18)	C19—P2	1.8210 (15)
C7—P1	1.8316 (12)	C20—C21	1.388 (2)
C8—C9	1.3905 (19)	C20—H20A	0.9500
C8—H8A	0.9500	C21—C22	1.375 (3)
C9—C10	1.377 (2)	C21—H21A	0.9500
C9—H9A	0.9500	C22—C23	1.372 (3)
C10—C11	1.382 (2)	C22—H22A	0.9500
C10—H10A	0.9500	C23—C24	1.389 (3)
C11—C12	1.3887 (19)	C23—H23A	0.9500
C11—H11A	0.9500	C24—H24A	0.9500
C12—H12A	0.9500	P1—P2	2.2263 (5)
C13—C18	1.391 (2)	P2—S1	1.9486 (5)

C6—C1—C2	118.73 (13)	C13—C14—H14A	120.1
C6—C1—P1	126.67 (10)	C16—C15—C14	120.26 (16)
C2—C1—P1	114.59 (10)	C16—C15—H15A	119.9
C3—C2—C1	120.75 (14)	C14—C15—H15A	119.9
C3—C2—H2A	119.6	C15—C16—C17	120.27 (15)
C1—C2—H2A	119.6	C15—C16—H16A	119.9
C4—C3—C2	119.83 (14)	C17—C16—H16A	119.9
C4—C3—H3A	120.1	C16—C17—C18	120.30 (15)
C2—C3—H3A	120.1	C16—C17—H17A	119.9
C3—C4—C5	120.19 (14)	C18—C17—H17A	119.9
C3—C4—H4A	119.9	C17—C18—C13	119.88 (16)
C5—C4—H4A	119.9	C17—C18—H18A	120.1
C4—C5—C6	120.24 (14)	C13—C18—H18A	120.1
C4—C5—H5A	119.9	C20—C19—C24	119.26 (14)
C6—C5—H5A	119.9	C20—C19—P2	121.44 (11)
C5—C6—C1	120.26 (13)	C24—C19—P2	119.23 (12)
C5—C6—H6A	119.9	C21—C20—C19	120.44 (16)
C1—C6—H6A	119.9	C21—C20—H20A	119.8
C8—C7—C12	118.85 (12)	C19—C20—H20A	119.8
C8—C7—P1	124.04 (10)	C22—C21—C20	119.80 (19)
C12—C7—P1	116.73 (10)	C22—C21—H21A	120.1
C9—C8—C7	120.35 (14)	C20—C21—H21A	120.1
C9—C8—H8A	119.8	C23—C22—C21	120.22 (17)
C7—C8—H8A	119.8	C23—C22—H22A	119.9
C10—C9—C8	120.45 (14)	C21—C22—H22A	119.9
C10—C9—H9A	119.8	C22—C23—C24	120.92 (17)
C8—C9—H9A	119.8	C22—C23—H23A	119.5
C9—C10—C11	119.63 (13)	C24—C23—H23A	119.5
C9—C10—H10A	120.2	C23—C24—C19	119.34 (18)
C11—C10—H10A	120.2	C23—C24—H24A	120.3
C10—C11—C12	120.40 (13)	C19—C24—H24A	120.3
C10—C11—H11A	119.8	C1—P1—C7	106.37 (6)
C12—C11—H11A	119.8	C1—P1—P2	100.58 (5)
C11—C12—C7	120.31 (13)	C7—P1—P2	99.63 (4)
C11—C12—H12A	119.8	C19—P2—C13	106.26 (6)
C7—C12—H12A	119.8	C19—P2—S1	112.51 (5)
C18—C13—C14	119.41 (13)	C13—P2—S1	113.05 (5)
C18—C13—P2	118.41 (11)	C19—P2—P1	102.26 (5)
C14—C13—P2	122.18 (11)	C13—P2—P1	103.00 (5)
C15—C14—C13	119.85 (16)	S1—P2—P1	118.43 (2)
C15—C14—H14A	120.1

C6—C1—C2—C3	0.4 (2)	C22—C23—C24—C19	−0.7 (3)
P1—C1—C2—C3	179.04 (11)	C20—C19—C24—C23	0.9 (2)
C1—C2—C3—C4	0.3 (2)	P2—C19—C24—C23	−176.34 (14)
C2—C3—C4—C5	−0.4 (2)	C6—C1—P1—C7	−52.24 (13)
C3—C4—C5—C6	−0.2 (2)	C2—C1—P1—C7	129.30 (10)
C4—C5—C6—C1	1.0 (2)	C6—C1—P1—P2	51.19 (12)
C2—C1—C6—C5	−1.1 (2)	C2—C1—P1—P2	−127.26 (10)
P1—C1—C6—C5	−179.48 (11)	C8—C7—P1—C1	−3.34 (14)
C12—C7—C8—C9	−0.6 (2)	C12—C7—P1—C1	−176.18 (10)
P1—C7—C8—C9	−173.34 (12)	C8—C7—P1—P2	−107.46 (12)
C7—C8—C9—C10	−0.1 (2)	C12—C7—P1—P2	79.70 (10)
C8—C9—C10—C11	0.5 (2)	C20—C19—P2—C13	41.29 (14)
C9—C10—C11—C12	−0.3 (2)	C24—C19—P2—C13	−141.56 (12)
C10—C11—C12—C7	−0.5 (2)	C20—C19—P2—S1	165.51 (11)
C8—C7—C12—C11	0.9 (2)	C24—C19—P2—S1	−17.34 (14)
P1—C7—C12—C11	174.15 (11)	C20—C19—P2—P1	−66.36 (12)
C18—C13—C14—C15	0.3 (2)	C24—C19—P2—P1	110.79 (12)
P2—C13—C14—C15	−179.17 (13)	C18—C13—P2—C19	97.09 (12)
C13—C14—C15—C16	−1.6 (3)	C14—C13—P2—C19	−83.43 (14)
C14—C15—C16—C17	1.7 (3)	C18—C13—P2—S1	−26.79 (13)
C15—C16—C17—C18	−0.5 (3)	C14—C13—P2—S1	152.68 (11)
C16—C17—C18—C13	−0.8 (2)	C18—C13—P2—P1	−155.79 (10)
C14—C13—C18—C17	0.9 (2)	C14—C13—P2—P1	23.68 (13)
P2—C13—C18—C17	−179.60 (12)	C1—P1—P2—C19	171.48 (6)
C24—C19—C20—C21	−0.1 (2)	C7—P1—P2—C19	−79.70 (6)
P2—C19—C20—C21	177.07 (13)	C1—P1—P2—C13	61.35 (6)
C19—C20—C21—C22	−0.9 (3)	C7—P1—P2—C13	170.16 (6)
C20—C21—C22—C23	1.1 (3)	C1—P1—P2—S1	−64.24 (5)
C21—C22—C23—C24	−0.3 (3)	C7—P1—P2—S1	44.58 (5)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀P₂S
M_r	402.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	9.32670 (19), 13.6496 (4), 16.0484 (4)
β (°)	91.7298 (17)
V (Å³)	2042.12 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.45 × 0.30 × 0.28

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Numerical (X-SHAPE; Stoe & Cie, 2005)
T_min, T_max	0.892, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	38972, 5499, 4493
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.096, 1.08
No. of reflections	5499
No. of parameters	244
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.28

Computer programs: X-AREA (Stoe & Cie, 2005), X-RED (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Leibniz-Institut für Katalyse e. V. an der Universität Rostock.

References

Bhattacharyya, P., Slawin, A. M. Z., Smith, M. B., Williams, D. J. & Woollins, J. D. (1996). J. Chem. Soc. Dalton Trans. pp. 3647–3651. CSD CrossRef Web of Science Google Scholar
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