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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1084.
Published online 2009 April 22. doi:  10.1107/S1600536809014238
PMCID: PMC2977763

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

Abstract

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 [triangle]); Bent et al. (1990 [triangle]); Simón-Manso et al. (2002 [triangle]); Ziegler & Weiss (1968 [triangle]). Synthesis of the starting compound Ph2PN(iPr)P(Ph)N(iPr)H was reported by Müller et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1084-scheme1.jpg

Experimental

Crystal data

  • C24H30N2P2S2
  • M r = 472.56
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1084-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.074
  • S = 1.02
  • 5561 reflections
  • 275 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.29 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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).

Refinement

Atom H2 attached to N2 was found on a difference Fourier map and refined isotropically. All other H atoms were placed in idealized positions with d(C—H) = 0.98 (CH3) and 0.95–1.00 Å (CH) and refined using a riding model with Uiso(H) fixed at 1.5 Ueq(C) for CH3 and 1.2 Ueq(C) for CH.

Figures

Fig. 1.
The molecular structure of the title compound showing the labelling scheme. Atomic displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C24H30N2P2S2F(000) = 1000
Mr = 472.56Dx = 1.294 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 32201 reflections
a = 9.08354 (19) Åθ = 1.6–29.6°
b = 25.4654 (7) ŵ = 0.37 mm1
c = 10.6557 (2) ÅT = 200 K
β = 100.1488 (17)°Prism, colourless
V = 2426.26 (10) Å30.45 × 0.25 × 0.20 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer5561 independent reflections
Radiation source: fine-focus sealed tube4459 reflections with I > 2σ(I)
graphiteRint = 0.032
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)h = −11→11
Tmin = 0.835, Tmax = 0.954k = −32→32
40233 measured reflectionsl = −13→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3
5561 reflections(Δ/σ)max = 0.001
275 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.28 e Å3

Special details

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)

xyzUiso*/Ueq
C10.10362 (14)0.36285 (5)0.96160 (12)0.0273 (3)
C20.03459 (17)0.41159 (5)0.96335 (13)0.0340 (3)
H2A−0.00410.42890.88550.041*
C30.02223 (19)0.43493 (6)1.07847 (14)0.0408 (3)
H3A−0.02620.46801.07940.049*
C40.0804 (2)0.41023 (6)1.19223 (14)0.0420 (4)
H4A0.07220.42641.27110.050*
C50.15020 (18)0.36216 (6)1.19100 (14)0.0390 (3)
H5A0.19080.34541.26910.047*
C60.16137 (15)0.33825 (6)1.07616 (13)0.0322 (3)
H6A0.20860.30501.07580.039*
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−0.18390.34170.88760.044*
C9−0.32629 (17)0.28415 (7)0.81026 (17)0.0457 (4)
H9A−0.40810.29540.84820.055*
C10−0.34149 (18)0.24077 (7)0.73275 (16)0.0444 (4)
H10A−0.43430.22270.71500.053*
C11−0.22185 (19)0.22362 (7)0.68090 (16)0.0450 (4)
H11A−0.23140.19320.62860.054*
C12−0.08742 (17)0.25057 (6)0.70473 (15)0.0382 (3)
H12A−0.00450.23800.67010.046*
C130.00109 (16)0.38464 (6)0.57993 (13)0.0356 (3)
H13A0.04780.41200.53230.043*
C14−0.14292 (18)0.40909 (7)0.60510 (17)0.0489 (4)
H14A−0.11960.43910.66280.073*
H14B−0.19980.38300.64440.073*
H14C−0.20260.42100.52440.073*
C15−0.0230 (2)0.33753 (7)0.49071 (15)0.0519 (4)
H15A0.07410.32380.47800.078*
H15B−0.08120.34830.40840.078*
H15C−0.07730.31010.52830.078*
C160.47654 (15)0.43480 (5)0.92161 (13)0.0312 (3)
H16A0.42240.46810.93410.037*
C170.5216 (2)0.40897 (7)1.05016 (16)0.0526 (5)
H17A0.43180.40071.08560.079*
H17B0.58540.43291.10780.079*
H17C0.57670.37661.04050.079*
C180.61096 (18)0.44872 (7)0.86165 (17)0.0447 (4)
H18A0.57710.46530.77860.067*
H18B0.66710.41670.85020.067*
H18C0.67550.47310.91740.067*
C190.34557 (15)0.40237 (5)0.57479 (12)0.0284 (3)
C200.39580 (17)0.35128 (6)0.56205 (13)0.0353 (3)
H20A0.37190.32450.61710.042*
C210.48033 (17)0.33927 (6)0.46965 (14)0.0387 (3)
H21A0.51540.30450.46210.046*
C220.51353 (17)0.37820 (6)0.38836 (13)0.0385 (3)
H22A0.57250.37020.32560.046*
C230.46149 (18)0.42831 (6)0.39823 (14)0.0411 (4)
H23A0.48310.45470.34100.049*
C240.37749 (17)0.44093 (6)0.49107 (13)0.0349 (3)
H24A0.34200.47580.49740.042*
N10.11346 (12)0.37534 (4)0.70123 (10)0.0262 (2)
N20.37172 (13)0.39982 (5)0.83996 (11)0.0284 (2)
H20.392 (2)0.3668 (8)0.8425 (17)0.047 (5)*
P10.10723 (4)0.328578 (13)0.81322 (3)0.02526 (8)
P20.25813 (4)0.418481 (13)0.71077 (3)0.02554 (8)
S10.26642 (4)0.275781 (13)0.82829 (4)0.03334 (9)
S20.20212 (4)0.491907 (14)0.71375 (3)0.03440 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0269 (6)0.0265 (6)0.0292 (6)−0.0029 (5)0.0068 (5)0.0017 (5)
C20.0442 (8)0.0298 (7)0.0289 (7)0.0034 (6)0.0086 (6)0.0017 (5)
C30.0550 (10)0.0326 (8)0.0375 (8)0.0051 (7)0.0156 (7)−0.0029 (6)
C40.0554 (10)0.0430 (9)0.0294 (7)−0.0052 (7)0.0122 (7)−0.0048 (6)
C50.0424 (8)0.0451 (9)0.0291 (7)−0.0018 (7)0.0052 (6)0.0054 (6)
C60.0317 (7)0.0325 (7)0.0331 (7)0.0000 (6)0.0073 (5)0.0054 (5)
C70.0267 (6)0.0282 (6)0.0330 (7)−0.0016 (5)0.0072 (5)0.0023 (5)
C80.0300 (7)0.0338 (7)0.0485 (8)0.0001 (6)0.0119 (6)−0.0020 (6)
C90.0288 (7)0.0477 (9)0.0627 (10)−0.0018 (7)0.0144 (7)0.0030 (8)
C100.0320 (8)0.0465 (9)0.0526 (9)−0.0124 (7)0.0017 (7)0.0090 (7)
C110.0451 (9)0.0409 (9)0.0476 (9)−0.0132 (7)0.0046 (7)−0.0073 (7)
C120.0363 (8)0.0358 (8)0.0439 (8)−0.0054 (6)0.0113 (6)−0.0072 (6)
C130.0334 (7)0.0448 (8)0.0270 (7)−0.0068 (6)0.0008 (6)0.0053 (6)
C140.0325 (8)0.0620 (11)0.0488 (9)0.0044 (7)−0.0019 (7)0.0148 (8)
C150.0611 (11)0.0634 (11)0.0297 (7)−0.0207 (9)0.0038 (7)−0.0062 (7)
C160.0304 (7)0.0290 (7)0.0332 (7)−0.0036 (5)0.0029 (5)−0.0045 (5)
C170.0590 (11)0.0577 (11)0.0356 (8)−0.0176 (8)−0.0068 (7)0.0018 (7)
C180.0335 (8)0.0423 (9)0.0588 (10)−0.0073 (7)0.0092 (7)−0.0004 (7)
C190.0267 (6)0.0305 (7)0.0282 (6)−0.0042 (5)0.0052 (5)−0.0006 (5)
C200.0418 (8)0.0318 (7)0.0351 (7)0.0000 (6)0.0143 (6)0.0012 (6)
C210.0420 (8)0.0396 (8)0.0366 (8)0.0024 (6)0.0127 (6)−0.0036 (6)
C220.0374 (8)0.0509 (9)0.0294 (7)−0.0050 (7)0.0117 (6)−0.0048 (6)
C230.0497 (9)0.0445 (9)0.0312 (7)−0.0092 (7)0.0129 (6)0.0032 (6)
C240.0402 (8)0.0327 (7)0.0327 (7)−0.0038 (6)0.0086 (6)0.0026 (5)
N10.0245 (5)0.0288 (6)0.0253 (5)−0.0024 (4)0.0042 (4)−0.0001 (4)
N20.0288 (6)0.0246 (6)0.0311 (6)−0.0022 (4)0.0035 (5)−0.0017 (4)
P10.02403 (16)0.02397 (16)0.02854 (16)−0.00070 (12)0.00670 (12)−0.00037 (12)
P20.02616 (16)0.02422 (16)0.02674 (16)−0.00164 (12)0.00604 (12)−0.00036 (12)
S10.02795 (17)0.02701 (17)0.0461 (2)0.00268 (13)0.00941 (14)0.00022 (14)
S20.03846 (19)0.02535 (17)0.04002 (19)0.00214 (14)0.00865 (15)0.00032 (13)

Geometric parameters (Å, °)

C1—C61.3900 (18)C15—H15A0.9800
C1—C21.3922 (19)C15—H15B0.9800
C1—P11.8113 (13)C15—H15C0.9800
C2—C31.385 (2)C16—N21.4714 (17)
C2—H2A0.9500C16—C171.510 (2)
C3—C41.385 (2)C16—C181.516 (2)
C3—H3A0.9500C16—H16A1.0000
C4—C51.380 (2)C17—H17A0.9800
C4—H4A0.9500C17—H17B0.9800
C5—C61.386 (2)C17—H17C0.9800
C5—H5A0.9500C18—H18A0.9800
C6—H6A0.9500C18—H18B0.9800
C7—C121.385 (2)C18—H18C0.9800
C7—C81.391 (2)C19—C241.3911 (19)
C7—P11.8173 (14)C19—C201.393 (2)
C8—C91.382 (2)C19—P21.8178 (14)
C8—H8A0.9500C20—C211.385 (2)
C9—C101.372 (2)C20—H20A0.9500
C9—H9A0.9500C21—C221.384 (2)
C10—C111.374 (2)C21—H21A0.9500
C10—H10A0.9500C22—C231.371 (2)
C11—C121.385 (2)C22—H22A0.9500
C11—H11A0.9500C23—C241.389 (2)
C12—H12A0.9500C23—H23A0.9500
C13—C141.515 (2)C24—H24A0.9500
C13—N11.5177 (16)N1—P11.6938 (11)
C13—C151.522 (2)N1—P21.7021 (11)
C13—H13A1.0000N2—P21.6386 (12)
C14—H14A0.9800N2—H20.860 (19)
C14—H14B0.9800P1—S11.9602 (5)
C14—H14C0.9800P2—S21.9395 (5)
C6—C1—C2119.42 (12)N2—C16—C17108.44 (12)
C6—C1—P1119.16 (10)N2—C16—C18112.18 (12)
C2—C1—P1121.25 (10)C17—C16—C18112.00 (13)
C3—C2—C1120.10 (13)N2—C16—H16A108.0
C3—C2—H2A120.0C17—C16—H16A108.0
C1—C2—H2A120.0C18—C16—H16A108.0
C4—C3—C2120.14 (14)C16—C17—H17A109.5
C4—C3—H3A119.9C16—C17—H17B109.5
C2—C3—H3A119.9H17A—C17—H17B109.5
C5—C4—C3119.97 (14)C16—C17—H17C109.5
C5—C4—H4A120.0H17A—C17—H17C109.5
C3—C4—H4A120.0H17B—C17—H17C109.5
C4—C5—C6120.22 (14)C16—C18—H18A109.5
C4—C5—H5A119.9C16—C18—H18B109.5
C6—C5—H5A119.9H18A—C18—H18B109.5
C5—C6—C1120.14 (13)C16—C18—H18C109.5
C5—C6—H6A119.9H18A—C18—H18C109.5
C1—C6—H6A119.9H18B—C18—H18C109.5
C12—C7—C8118.70 (13)C24—C19—C20119.20 (13)
C12—C7—P1119.36 (11)C24—C19—P2121.44 (11)
C8—C7—P1121.67 (11)C20—C19—P2119.01 (10)
C9—C8—C7120.14 (14)C21—C20—C19120.49 (13)
C9—C8—H8A119.9C21—C20—H20A119.8
C7—C8—H8A119.9C19—C20—H20A119.8
C10—C9—C8120.65 (15)C22—C21—C20119.73 (15)
C10—C9—H9A119.7C22—C21—H21A120.1
C8—C9—H9A119.7C20—C21—H21A120.1
C9—C10—C11119.69 (14)C23—C22—C21120.16 (14)
C9—C10—H10A120.2C23—C22—H22A119.9
C11—C10—H10A120.2C21—C22—H22A119.9
C10—C11—C12120.20 (15)C22—C23—C24120.66 (14)
C10—C11—H11A119.9C22—C23—H23A119.7
C12—C11—H11A119.9C24—C23—H23A119.7
C11—C12—C7120.53 (14)C23—C24—C19119.74 (14)
C11—C12—H12A119.7C23—C24—H24A120.1
C7—C12—H12A119.7C19—C24—H24A120.1
C14—C13—N1112.68 (12)C13—N1—P1127.50 (9)
C14—C13—C15113.63 (14)C13—N1—P2110.27 (8)
N1—C13—C15114.19 (13)P1—N1—P2122.20 (6)
C14—C13—H13A105.1C16—N2—P2124.56 (10)
N1—C13—H13A105.1C16—N2—H2117.2 (12)
C15—C13—H13A105.1P2—N2—H2114.3 (12)
C13—C14—H14A109.5N1—P1—C1106.51 (6)
C13—C14—H14B109.5N1—P1—C7108.78 (6)
H14A—C14—H14B109.5C1—P1—C7104.21 (6)
C13—C14—H14C109.5N1—P1—S1115.10 (4)
H14A—C14—H14C109.5C1—P1—S1112.68 (5)
H14B—C14—H14C109.5C7—P1—S1108.95 (5)
C13—C15—H15A109.5N2—P2—N1103.20 (6)
C13—C15—H15B109.5N2—P2—C19107.78 (6)
H15A—C15—H15B109.5N1—P2—C19104.35 (6)
C13—C15—H15C109.5N2—P2—S2113.21 (5)
H15A—C15—H15C109.5N1—P2—S2114.92 (4)
H15B—C15—H15C109.5C19—P2—S2112.54 (5)
C6—C1—C2—C3−0.8 (2)C13—N1—P1—C7−8.37 (13)
P1—C1—C2—C3174.52 (12)P2—N1—P1—C7173.69 (7)
C1—C2—C3—C40.9 (2)C13—N1—P1—S1114.18 (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—C10.7 (2)C2—C1—P1—N132.18 (13)
C2—C1—C6—C50.0 (2)C6—C1—P1—C792.55 (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—S1159.29 (10)
C7—C8—C9—C100.0 (3)C12—C7—P1—N192.52 (12)
C8—C9—C10—C111.9 (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—C119.89 (13)
C8—C7—C12—C113.3 (2)C12—C7—P1—S1−33.67 (13)
P1—C7—C12—C11177.57 (12)C8—C7—P1—S1140.39 (11)
C24—C19—C20—C211.9 (2)C16—N2—P2—N1−152.15 (11)
P2—C19—C20—C21−171.38 (11)C16—N2—P2—C1997.82 (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—C241.2 (2)P1—N1—P2—N22.28 (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—C19114.84 (8)
P2—C19—C24—C23171.67 (11)C13—N1—P2—S260.30 (10)
C14—C13—N1—P173.52 (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—N252.61 (13)
C15—C13—N1—P2120.05 (12)C24—C19—P2—N1130.24 (11)
C17—C16—N2—P2161.08 (12)C20—C19—P2—N1−56.62 (12)
C18—C16—N2—P2−74.69 (15)C24—C19—P2—S25.00 (13)
C13—N1—P1—C1−120.16 (12)C20—C19—P2—S2178.14 (10)
P2—N1—P1—C161.90 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···S10.860 (19)2.578 (19)3.2963 (12)141.7 (16)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2547).

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