organic compounds
P-[N-(Diphenylphosphorothioyl)isopropylamino]-N-isopropyl-P-phenylthiophosphinic amide
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
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
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2005); cell 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
10.1107/S1600536809014238/cv2547sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809014238/cv2547Isup2.hkl
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).
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.
Data collection: X-AREA (Stoe & Cie, 2005); cell
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).Fig. 1. The molecular structure of the title compound showing the labelling scheme. Atomic displacement ellipsoids are drawn at the 30% probability level. |
C24H30N2P2S2 | F(000) = 1000 |
Mr = 472.56 | Dx = 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 |
Stoe IPDS-II diffractometer | 5561 independent reflections |
Radiation source: fine-focus sealed tube | 4459 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 27.5°, θmin = 1.6° |
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005) | h = −11→11 |
Tmin = 0.835, Tmax = 0.954 | k = −32→32 |
40233 measured reflections | l = −13→13 |
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(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3 |
5561 reflections | (Δ/σ)max = 0.001 |
275 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C24H30N2P2S2 | V = 2426.26 (10) Å3 |
Mr = 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)° |
Stoe IPDS-II diffractometer | 5561 independent reflections |
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005) | 4459 reflections with I > 2σ(I) |
Tmin = 0.835, Tmax = 0.954 | Rint = 0.032 |
40233 measured reflections |
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 | Δρmax = 0.21 e Å−3 |
5561 reflections | Δρmin = −0.29 e Å−3 |
275 parameters |
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 | 0.10362 (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) |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.835, 0.954 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 40233, 5561, 4459 |
Rint | 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 |
Δρmax, Δρmin (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).
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
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.