P-[N-(Diphenyl­phospho­rothio­yl)iso­propyl­amino]-N-isopropyl-P-phenyl­thio­phosphinic amide

Peulecke, N.; Aluri, B.R.; Wöhl, A.; Spannenberg, A.; Al-Hazmi, M.H.

doi:10.1107/S1600536809014238

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1084

doi:10.1107/S1600536809014238

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P-[N-(Diphenylphosphorothioyl)isopropylamino]-N-isopropyl-P-phenylthiophosphinic amide

Normen Peulecke,^a ^* Bhaskar R. Aluri,^a Anina Wöhl,^b Anke Spannenberg ^a and Mohammed H. Al-Hazmi ^c

^aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany, ^bLinde AG, Linde Engineering Division, Dr-Carl-von-Linde-Strasse 6-14, 82049 Pullach, Germany, and ^cSabic R&T Complex, Catalysis and Specialty Section, Chemical Research Department, PO Box 42503, Riyadh 11551, Saudi Arabia
^*Correspondence e-mail: normen.peulecke@catalysis.de

(Received 6 April 2009; accepted 16 April 2009; online 22 April 2009)

The title compound, C₂₄H₃₀N₂P₂S₂, was obtained by the reaction of Ph₂PN(iPr)P(Ph)N(iPr)H with elemental sulfur in tetrahydrofuran. In the solid state, intramolecular N—H⋯S hydrogen bonding influences the molecular conformation; a P—N—P—N torsion angle of 2.28 (9)° is observed. The two phenyl rings attached to one P atom form a dihedral angle of 74.02 (4)°.

Related literature

For the crystal structures of similar compounds, see: Alouani et al. (2007 ); Bent et al. (1990 ); Simón-Manso et al. (2002 ); Ziegler & Weiss (1968 ). Synthesis of the starting compound Ph₂PN(iPr)P(Ph)N(iPr)H was reported by Müller et al. (2009 ).

Experimental

Crystal data

C₂₄H₃₀N₂P₂S₂
M_r = 472.56
Monoclinic, P 2₁ /c
a = 9.08354 (19) Å
b = 25.4654 (7) Å
c = 10.6557 (2) Å
β = 100.1488 (17)°
V = 2426.26 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 200 K
0.45 × 0.25 × 0.20 mm

Data collection

Stoe IPDS-II diffractometer
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ) T_min = 0.835, T_max = 0.954
40233 measured reflections
5561 independent reflections
4459 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.074
S = 1.02
5561 reflections
275 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1	0.860 (19)	2.578 (19)	3.2963 (12)	141.7 (16)

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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014238/cv2547sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014238/cv2547Isup2.hkl

checkCIF report

Comment top

Linear phosphazanes can act as chelate ligands containing both hard (nitrogen) and soft (phosphorus) donor atoms. Often these compounds are thermally unstable and undergo rapid oxidation. Crystal structures of the compounds with a P(S)–N–P(S) unit are already known e.g. [(Me₂N)₂P(S)]₂NMe (Alouani et al., 2007), C₆H₄(NH)P(S)EtNP(S)(NEt₂)Et (Bent et al., 1990), [Ph₂P(S)]₂N(CHMePh) (Simón-Manso et al., 2002) and NH₂(NHMe)P(S)N(Me)P(S)(NH₂)₂ (Ziegler et al., 1968). In the present publication, we report on the formation and molecular structure of C₂₄H₃₀N₂P₂S₂, which was observed to be the single product of a complete oxidation of Ph₂PN(iPr)P(Ph)N(iPr)H with sulfur. The starting compound was synthesized as described in the patent WO 2009006979 (Müller et al., 2009).

In the solid state a torsion angle P1—N1—P2—N2 of 2.28 (9)° was found for the title compound. The two phenyl rings attached to P1 form a dihedral angle of 74.02 (4)°. A weak intramolecular hydrogen bond N2—H2···S1 (Table 1) was observed.

Related literature top

For the crystal structures of similar compounds, see: Alouani et al. (2007); Bent et al. (1990); Simón-Manso et al. (2002); Ziegler et al. (1968). Synthesis of the starting compound Ph₂PN(iPr)P(Ph)N(iPr)H was reported by Müller et al. (2009).

Experimental top

204 mg (0,5 mmol) Ph₂PN(iPr)P(Ph)N(iPr)H and 38.5 mg (1.2 mmol) sulfur were solved in 10 ml tetrahydrofuran and stirred for 24 h at 40°C. The solution was filtrated to remove unreacted sulfur. The major part of tetrahydrofuran was removed and the remaining solution was over-layered with n-hexane to get single crystals of the title compound, which are suitable for X-ray analysis. The white compound was fully characterized by standard analytical methods e.g. ³¹P NMR: (C₆D₆): 73.7, 65.9 (broad).

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: XP in 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 labelling scheme. Atomic displacement ellipsoids are drawn at the 30% probability level.

P-[N-(Diphenylphosphorothioyl)isopropylamino]-N- isopropyl-P-phenylthiophosphinic amide top

Crystal data top

C₂₄H₃₀N₂P₂S₂	F(000) = 1000
M_r = 472.56	D_x = 1.294 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 32201 reflections
a = 9.08354 (19) Å	θ = 1.6–29.6°
b = 25.4654 (7) Å	µ = 0.37 mm⁻¹
c = 10.6557 (2) Å	T = 200 K
β = 100.1488 (17)°	Prism, colourless
V = 2426.26 (10) Å³	0.45 × 0.25 × 0.20 mm
Z = 4

Data collection top

Stoe IPDS-II diffractometer	5561 independent reflections
Radiation source: fine-focus sealed tube	4459 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	h = −11→11
T_min = 0.835, T_max = 0.954	k = −32→32
40233 measured reflections	l = −13→13

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0472P)²] where P = (F_o² + 2F_c²)/3
5561 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₄H₃₀N₂P₂S₂	V = 2426.26 (10) Å³
M_r = 472.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.08354 (19) Å	µ = 0.37 mm⁻¹
b = 25.4654 (7) Å	T = 200 K
c = 10.6557 (2) Å	0.45 × 0.25 × 0.20 mm
β = 100.1488 (17)°

Data collection top

Stoe IPDS-II diffractometer	5561 independent reflections
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	4459 reflections with I > 2σ(I)
T_min = 0.835, T_max = 0.954	R_int = 0.032
40233 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.21 e Å⁻³
5561 reflections	Δρ_min = −0.29 e Å⁻³
275 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	0.10362 (14)	0.36285 (5)	0.96160 (12)	0.0273 (3)
C2	0.03459 (17)	0.41159 (5)	0.96335 (13)	0.0340 (3)
H2A	−0.0041	0.4289	0.8855	0.041*
C3	0.02223 (19)	0.43493 (6)	1.07847 (14)	0.0408 (3)
H3A	−0.0262	0.4680	1.0794	0.049*
C4	0.0804 (2)	0.41023 (6)	1.19223 (14)	0.0420 (4)
H4A	0.0722	0.4264	1.2711	0.050*
C5	0.15020 (18)	0.36216 (6)	1.19100 (14)	0.0390 (3)
H5A	0.1908	0.3454	1.2691	0.047*
C6	0.16137 (15)	0.33825 (6)	1.07616 (13)	0.0322 (3)
H6A	0.2086	0.3050	1.0758	0.039*
C7	−0.07285 (15)	0.29565 (5)	0.77859 (13)	0.0291 (3)
C8	−0.19321 (16)	0.31171 (6)	0.83371 (15)	0.0368 (3)
H8A	−0.1839	0.3417	0.8876	0.044*
C9	−0.32629 (17)	0.28415 (7)	0.81026 (17)	0.0457 (4)
H9A	−0.4081	0.2954	0.8482	0.055*
C10	−0.34149 (18)	0.24077 (7)	0.73275 (16)	0.0444 (4)
H10A	−0.4343	0.2227	0.7150	0.053*
C11	−0.22185 (19)	0.22362 (7)	0.68090 (16)	0.0450 (4)
H11A	−0.2314	0.1932	0.6286	0.054*
C12	−0.08742 (17)	0.25057 (6)	0.70473 (15)	0.0382 (3)
H12A	−0.0045	0.2380	0.6701	0.046*
C13	0.00109 (16)	0.38464 (6)	0.57993 (13)	0.0356 (3)
H13A	0.0478	0.4120	0.5323	0.043*
C14	−0.14292 (18)	0.40909 (7)	0.60510 (17)	0.0489 (4)
H14A	−0.1196	0.4391	0.6628	0.073*
H14B	−0.1998	0.3830	0.6444	0.073*
H14C	−0.2026	0.4210	0.5244	0.073*
C15	−0.0230 (2)	0.33753 (7)	0.49071 (15)	0.0519 (4)
H15A	0.0741	0.3238	0.4780	0.078*
H15B	−0.0812	0.3483	0.4084	0.078*
H15C	−0.0773	0.3101	0.5283	0.078*
C16	0.47654 (15)	0.43480 (5)	0.92161 (13)	0.0312 (3)
H16A	0.4224	0.4681	0.9341	0.037*
C17	0.5216 (2)	0.40897 (7)	1.05016 (16)	0.0526 (5)
H17A	0.4318	0.4007	1.0856	0.079*
H17B	0.5854	0.4329	1.1078	0.079*
H17C	0.5767	0.3766	1.0405	0.079*
C18	0.61096 (18)	0.44872 (7)	0.86165 (17)	0.0447 (4)
H18A	0.5771	0.4653	0.7786	0.067*
H18B	0.6671	0.4167	0.8502	0.067*
H18C	0.6755	0.4731	0.9174	0.067*
C19	0.34557 (15)	0.40237 (5)	0.57479 (12)	0.0284 (3)
C20	0.39580 (17)	0.35128 (6)	0.56205 (13)	0.0353 (3)
H20A	0.3719	0.3245	0.6171	0.042*
C21	0.48033 (17)	0.33927 (6)	0.46965 (14)	0.0387 (3)
H21A	0.5154	0.3045	0.4621	0.046*
C22	0.51353 (17)	0.37820 (6)	0.38836 (13)	0.0385 (3)
H22A	0.5725	0.3702	0.3256	0.046*
C23	0.46149 (18)	0.42831 (6)	0.39823 (14)	0.0411 (4)
H23A	0.4831	0.4547	0.3410	0.049*
C24	0.37749 (17)	0.44093 (6)	0.49107 (13)	0.0349 (3)
H24A	0.3420	0.4758	0.4974	0.042*
N1	0.11346 (12)	0.37534 (4)	0.70123 (10)	0.0262 (2)
N2	0.37172 (13)	0.39982 (5)	0.83996 (11)	0.0284 (2)
H2	0.392 (2)	0.3668 (8)	0.8425 (17)	0.047 (5)*
P1	0.10723 (4)	0.328578 (13)	0.81322 (3)	0.02526 (8)
P2	0.25813 (4)	0.418481 (13)	0.71077 (3)	0.02554 (8)
S1	0.26642 (4)	0.275781 (13)	0.82829 (4)	0.03334 (9)
S2	0.20212 (4)	0.491907 (14)	0.71375 (3)	0.03440 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0269 (6)	0.0265 (6)	0.0292 (6)	−0.0029 (5)	0.0068 (5)	0.0017 (5)
C2	0.0442 (8)	0.0298 (7)	0.0289 (7)	0.0034 (6)	0.0086 (6)	0.0017 (5)
C3	0.0550 (10)	0.0326 (8)	0.0375 (8)	0.0051 (7)	0.0156 (7)	−0.0029 (6)
C4	0.0554 (10)	0.0430 (9)	0.0294 (7)	−0.0052 (7)	0.0122 (7)	−0.0048 (6)
C5	0.0424 (8)	0.0451 (9)	0.0291 (7)	−0.0018 (7)	0.0052 (6)	0.0054 (6)
C6	0.0317 (7)	0.0325 (7)	0.0331 (7)	0.0000 (6)	0.0073 (5)	0.0054 (5)
C7	0.0267 (6)	0.0282 (6)	0.0330 (7)	−0.0016 (5)	0.0072 (5)	0.0023 (5)
C8	0.0300 (7)	0.0338 (7)	0.0485 (8)	0.0001 (6)	0.0119 (6)	−0.0020 (6)
C9	0.0288 (7)	0.0477 (9)	0.0627 (10)	−0.0018 (7)	0.0144 (7)	0.0030 (8)
C10	0.0320 (8)	0.0465 (9)	0.0526 (9)	−0.0124 (7)	0.0017 (7)	0.0090 (7)
C11	0.0451 (9)	0.0409 (9)	0.0476 (9)	−0.0132 (7)	0.0046 (7)	−0.0073 (7)
C12	0.0363 (8)	0.0358 (8)	0.0439 (8)	−0.0054 (6)	0.0113 (6)	−0.0072 (6)
C13	0.0334 (7)	0.0448 (8)	0.0270 (7)	−0.0068 (6)	0.0008 (6)	0.0053 (6)
C14	0.0325 (8)	0.0620 (11)	0.0488 (9)	0.0044 (7)	−0.0019 (7)	0.0148 (8)
C15	0.0611 (11)	0.0634 (11)	0.0297 (7)	−0.0207 (9)	0.0038 (7)	−0.0062 (7)
C16	0.0304 (7)	0.0290 (7)	0.0332 (7)	−0.0036 (5)	0.0029 (5)	−0.0045 (5)
C17	0.0590 (11)	0.0577 (11)	0.0356 (8)	−0.0176 (8)	−0.0068 (7)	0.0018 (7)
C18	0.0335 (8)	0.0423 (9)	0.0588 (10)	−0.0073 (7)	0.0092 (7)	−0.0004 (7)
C19	0.0267 (6)	0.0305 (7)	0.0282 (6)	−0.0042 (5)	0.0052 (5)	−0.0006 (5)
C20	0.0418 (8)	0.0318 (7)	0.0351 (7)	0.0000 (6)	0.0143 (6)	0.0012 (6)
C21	0.0420 (8)	0.0396 (8)	0.0366 (8)	0.0024 (6)	0.0127 (6)	−0.0036 (6)
C22	0.0374 (8)	0.0509 (9)	0.0294 (7)	−0.0050 (7)	0.0117 (6)	−0.0048 (6)
C23	0.0497 (9)	0.0445 (9)	0.0312 (7)	−0.0092 (7)	0.0129 (6)	0.0032 (6)
C24	0.0402 (8)	0.0327 (7)	0.0327 (7)	−0.0038 (6)	0.0086 (6)	0.0026 (5)
N1	0.0245 (5)	0.0288 (6)	0.0253 (5)	−0.0024 (4)	0.0042 (4)	−0.0001 (4)
N2	0.0288 (6)	0.0246 (6)	0.0311 (6)	−0.0022 (4)	0.0035 (5)	−0.0017 (4)
P1	0.02403 (16)	0.02397 (16)	0.02854 (16)	−0.00070 (12)	0.00670 (12)	−0.00037 (12)
P2	0.02616 (16)	0.02422 (16)	0.02674 (16)	−0.00164 (12)	0.00604 (12)	−0.00036 (12)
S1	0.02795 (17)	0.02701 (17)	0.0461 (2)	0.00268 (13)	0.00941 (14)	0.00022 (14)
S2	0.03846 (19)	0.02535 (17)	0.04002 (19)	0.00214 (14)	0.00865 (15)	0.00032 (13)

Geometric parameters (Å, º) top

C1—C6	1.3900 (18)	C15—H15A	0.9800
C1—C2	1.3922 (19)	C15—H15B	0.9800
C1—P1	1.8113 (13)	C15—H15C	0.9800
C2—C3	1.385 (2)	C16—N2	1.4714 (17)
C2—H2A	0.9500	C16—C17	1.510 (2)
C3—C4	1.385 (2)	C16—C18	1.516 (2)
C3—H3A	0.9500	C16—H16A	1.0000
C4—C5	1.380 (2)	C17—H17A	0.9800
C4—H4A	0.9500	C17—H17B	0.9800
C5—C6	1.386 (2)	C17—H17C	0.9800
C5—H5A	0.9500	C18—H18A	0.9800
C6—H6A	0.9500	C18—H18B	0.9800
C7—C12	1.385 (2)	C18—H18C	0.9800
C7—C8	1.391 (2)	C19—C24	1.3911 (19)
C7—P1	1.8173 (14)	C19—C20	1.393 (2)
C8—C9	1.382 (2)	C19—P2	1.8178 (14)
C8—H8A	0.9500	C20—C21	1.385 (2)
C9—C10	1.372 (2)	C20—H20A	0.9500
C9—H9A	0.9500	C21—C22	1.384 (2)
C10—C11	1.374 (2)	C21—H21A	0.9500
C10—H10A	0.9500	C22—C23	1.371 (2)
C11—C12	1.385 (2)	C22—H22A	0.9500
C11—H11A	0.9500	C23—C24	1.389 (2)
C12—H12A	0.9500	C23—H23A	0.9500
C13—C14	1.515 (2)	C24—H24A	0.9500
C13—N1	1.5177 (16)	N1—P1	1.6938 (11)
C13—C15	1.522 (2)	N1—P2	1.7021 (11)
C13—H13A	1.0000	N2—P2	1.6386 (12)
C14—H14A	0.9800	N2—H2	0.860 (19)
C14—H14B	0.9800	P1—S1	1.9602 (5)
C14—H14C	0.9800	P2—S2	1.9395 (5)

C6—C1—C2	119.42 (12)	N2—C16—C17	108.44 (12)
C6—C1—P1	119.16 (10)	N2—C16—C18	112.18 (12)
C2—C1—P1	121.25 (10)	C17—C16—C18	112.00 (13)
C3—C2—C1	120.10 (13)	N2—C16—H16A	108.0
C3—C2—H2A	120.0	C17—C16—H16A	108.0
C1—C2—H2A	120.0	C18—C16—H16A	108.0
C4—C3—C2	120.14 (14)	C16—C17—H17A	109.5
C4—C3—H3A	119.9	C16—C17—H17B	109.5
C2—C3—H3A	119.9	H17A—C17—H17B	109.5
C5—C4—C3	119.97 (14)	C16—C17—H17C	109.5
C5—C4—H4A	120.0	H17A—C17—H17C	109.5
C3—C4—H4A	120.0	H17B—C17—H17C	109.5
C4—C5—C6	120.22 (14)	C16—C18—H18A	109.5
C4—C5—H5A	119.9	C16—C18—H18B	109.5
C6—C5—H5A	119.9	H18A—C18—H18B	109.5
C5—C6—C1	120.14 (13)	C16—C18—H18C	109.5
C5—C6—H6A	119.9	H18A—C18—H18C	109.5
C1—C6—H6A	119.9	H18B—C18—H18C	109.5
C12—C7—C8	118.70 (13)	C24—C19—C20	119.20 (13)
C12—C7—P1	119.36 (11)	C24—C19—P2	121.44 (11)
C8—C7—P1	121.67 (11)	C20—C19—P2	119.01 (10)
C9—C8—C7	120.14 (14)	C21—C20—C19	120.49 (13)
C9—C8—H8A	119.9	C21—C20—H20A	119.8
C7—C8—H8A	119.9	C19—C20—H20A	119.8
C10—C9—C8	120.65 (15)	C22—C21—C20	119.73 (15)
C10—C9—H9A	119.7	C22—C21—H21A	120.1
C8—C9—H9A	119.7	C20—C21—H21A	120.1
C9—C10—C11	119.69 (14)	C23—C22—C21	120.16 (14)
C9—C10—H10A	120.2	C23—C22—H22A	119.9
C11—C10—H10A	120.2	C21—C22—H22A	119.9
C10—C11—C12	120.20 (15)	C22—C23—C24	120.66 (14)
C10—C11—H11A	119.9	C22—C23—H23A	119.7
C12—C11—H11A	119.9	C24—C23—H23A	119.7
C11—C12—C7	120.53 (14)	C23—C24—C19	119.74 (14)
C11—C12—H12A	119.7	C23—C24—H24A	120.1
C7—C12—H12A	119.7	C19—C24—H24A	120.1
C14—C13—N1	112.68 (12)	C13—N1—P1	127.50 (9)
C14—C13—C15	113.63 (14)	C13—N1—P2	110.27 (8)
N1—C13—C15	114.19 (13)	P1—N1—P2	122.20 (6)
C14—C13—H13A	105.1	C16—N2—P2	124.56 (10)
N1—C13—H13A	105.1	C16—N2—H2	117.2 (12)
C15—C13—H13A	105.1	P2—N2—H2	114.3 (12)
C13—C14—H14A	109.5	N1—P1—C1	106.51 (6)
C13—C14—H14B	109.5	N1—P1—C7	108.78 (6)
H14A—C14—H14B	109.5	C1—P1—C7	104.21 (6)
C13—C14—H14C	109.5	N1—P1—S1	115.10 (4)
H14A—C14—H14C	109.5	C1—P1—S1	112.68 (5)
H14B—C14—H14C	109.5	C7—P1—S1	108.95 (5)
C13—C15—H15A	109.5	N2—P2—N1	103.20 (6)
C13—C15—H15B	109.5	N2—P2—C19	107.78 (6)
H15A—C15—H15B	109.5	N1—P2—C19	104.35 (6)
C13—C15—H15C	109.5	N2—P2—S2	113.21 (5)
H15A—C15—H15C	109.5	N1—P2—S2	114.92 (4)
H15B—C15—H15C	109.5	C19—P2—S2	112.54 (5)

C6—C1—C2—C3	−0.8 (2)	C13—N1—P1—C7	−8.37 (13)
P1—C1—C2—C3	174.52 (12)	P2—N1—P1—C7	173.69 (7)
C1—C2—C3—C4	0.9 (2)	C13—N1—P1—S1	114.18 (11)
C2—C3—C4—C5	−0.3 (3)	P2—N1—P1—S1	−63.76 (8)
C3—C4—C5—C6	−0.5 (2)	C6—C1—P1—N1	−152.53 (10)
C4—C5—C6—C1	0.7 (2)	C2—C1—P1—N1	32.18 (13)
C2—C1—C6—C5	0.0 (2)	C6—C1—P1—C7	92.55 (11)
P1—C1—C6—C5	−175.41 (11)	C2—C1—P1—C7	−82.74 (12)
C12—C7—C8—C9	−2.7 (2)	C6—C1—P1—S1	−25.41 (12)
P1—C7—C8—C9	−176.74 (12)	C2—C1—P1—S1	159.29 (10)
C7—C8—C9—C10	0.0 (3)	C12—C7—P1—N1	92.52 (12)
C8—C9—C10—C11	1.9 (3)	C8—C7—P1—N1	−93.43 (13)
C9—C10—C11—C12	−1.3 (3)	C12—C7—P1—C1	−154.16 (12)
C10—C11—C12—C7	−1.4 (2)	C8—C7—P1—C1	19.89 (13)
C8—C7—C12—C11	3.3 (2)	C12—C7—P1—S1	−33.67 (13)
P1—C7—C12—C11	177.57 (12)	C8—C7—P1—S1	140.39 (11)
C24—C19—C20—C21	1.9 (2)	C16—N2—P2—N1	−152.15 (11)
P2—C19—C20—C21	−171.38 (11)	C16—N2—P2—C19	97.82 (12)
C19—C20—C21—C22	−0.8 (2)	C16—N2—P2—S2	−27.31 (12)
C20—C21—C22—C23	−0.8 (2)	C13—N1—P2—N2	−175.97 (9)
C21—C22—C23—C24	1.2 (2)	P1—N1—P2—N2	2.28 (9)
C22—C23—C24—C19	−0.1 (2)	C13—N1—P2—C19	−63.41 (10)
C20—C19—C24—C23	−1.5 (2)	P1—N1—P2—C19	114.84 (8)
P2—C19—C24—C23	171.67 (11)	C13—N1—P2—S2	60.30 (10)
C14—C13—N1—P1	73.52 (16)	P1—N1—P2—S2	−121.44 (6)
C15—C13—N1—P1	−58.09 (17)	C24—C19—P2—N2	−120.52 (12)
C14—C13—N1—P2	−108.34 (12)	C20—C19—P2—N2	52.61 (13)
C15—C13—N1—P2	120.05 (12)	C24—C19—P2—N1	130.24 (11)
C17—C16—N2—P2	161.08 (12)	C20—C19—P2—N1	−56.62 (12)
C18—C16—N2—P2	−74.69 (15)	C24—C19—P2—S2	5.00 (13)
C13—N1—P1—C1	−120.16 (12)	C20—C19—P2—S2	178.14 (10)
P2—N1—P1—C1	61.90 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1	0.860 (19)	2.578 (19)	3.2963 (12)	141.7 (16)

Experimental details

Crystal data
Chemical formula	C₂₄H₃₀N₂P₂S₂
M_r	472.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	9.08354 (19), 25.4654 (7), 10.6557 (2)
β (°)	100.1488 (17)
V (Å³)	2426.26 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.45 × 0.25 × 0.20

Data collection
Diffractometer	Stoe IPDS-II diffractometer
Absorption correction	Numerical (X-SHAPE; Stoe & Cie, 2005)
T_min, T_max	0.835, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	40233, 5561, 4459
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.074, 1.02
No. of reflections	5561
No. of parameters	275
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.29

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1	0.860 (19)	2.578 (19)	3.2963 (12)	141.7 (16)

Acknowledgements

This work was supported by the Leibniz-Institut für Katalyse e. V. an der Universität Rostock. The authors thank Professor Uwe Rosenthal for his support.

References

Alouani, K., Raouafi, N. & Guesmi, A. (2007). Struct. Chem. 18, 569–572. Web of Science CSD CrossRef CAS Google Scholar
Bent, E. G., Schaeffer, R., Haltiwanger, R. C. & Norman, A. D. (1990). Inorg. Chem. 29, 2608–2613. CSD CrossRef CAS Web of Science Google Scholar
Müller, B. H., Fritz, P., Bölt, H., Wöhl, A., Müller, W., Winkler, F., Wellenhofer, A., Rosenthal, U., Hapke, M., Peulecke, N., Al-Hazmi, M. H., Aliyev, V. O. & Mosa, F. M. (2009). WO Patent No. 2009006979. (Linde AG, Saudi Basic Industries Corporation, January 15, 2009.) Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Simón-Manso, E., Valderrama, M., Gantzel, P. & Kubiak, C. P. (2002). J. Organomet. Chem. 651, 90–97. Google Scholar
Stoe & Cie (2005). X-SHAPE, X-RED and X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Ziegler, M. L. & Weiss, J. (1968). Z. Anorg. Allg. Chem. 361, 136–146. CSD CrossRef CAS Web of Science Google Scholar

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Volume 65| Part 5| May 2009| Page o1084

doi:10.1107/S1600536809014238

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

P-[N-(Di­phenyl­phospho­ro­thio­yl)iso­propyl­amino]-N-iso­propyl-P-phenyl­thio­phosphinic amide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

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organic compounds

P-[N-(Diphenylphosphorothioyl)isopropylamino]-N-isopropyl-P-phenylthiophosphinic amide