Acta Cryst. (2011). E67, o1474 [ doi:10.1107/S1600536811018551 ]
The title compound, C9H22NOP, was obtained by slow diffusion of oxygen into a toluene solution of iPr2PNHiPr. In the crystal, an intermolecular N-H
O hydrogen bond occurs.
A toluene solution (20 mL) of 0.4 g (2.3 mmol) (iPr)2PN(H)iPr (Kuchen et al., 1990) was exposed to dry air over a period of 48 h. After evaporation of the solvent, the oily residue was dissolved in n-hexane, filtrated and stored at -40°C for crystallization. After 3 days colourless crystals were formed, which were suitable for X-ray analysis. The analytical data of C9H22NOP correlated with those in the literature (Brück et al., 1995).
H atoms were placed in idealized positions with d(N—H) = 0.88, d(C—H) = 0.98 (CH3) and 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 NH and CH.
Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (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: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./yk2008fig1thm.gif)
| Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
| C9H22NOP | F(000) = 424 |
| Mr = 191.25 | Dx = 1.037 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 5563 reflections |
| a = 15.030 (3) Å | θ = 2.1–29.2° |
| b = 8.4813 (17) Å | µ = 0.19 mm−1 |
| c = 10.071 (2) Å | T = 195 K |
| β = 107.36 (3)° | Prism, colourless |
| V = 1225.3 (4) Å3 | 0.42 × 0.26 × 0.20 mm |
| Z = 4 |
| Stoe IPDS II diffractometer | 2012 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.035 |
| graphite | θmax = 27.5°, θmin = 2.8° |
| ω scans | h = −19→19 |
| 19581 measured reflections | k = −11→11 |
| 2807 independent 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.091 | H-atom parameters constrained |
| S = 0.89 | w = 1/[σ2(Fo2) + (0.0547P)2] where P = (Fo2 + 2Fc2)/3 |
| 2807 reflections | (Δ/σ)max = 0.001 |
| 115 parameters | Δρmax = 0.39 e Å−3 |
| 0 restraints | Δρmin = −0.16 e Å−3 |
| C9H22NOP | V = 1225.3 (4) Å3 |
| Mr = 191.25 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 15.030 (3) Å | µ = 0.19 mm−1 |
| b = 8.4813 (17) Å | T = 195 K |
| c = 10.071 (2) Å | 0.42 × 0.26 × 0.20 mm |
| β = 107.36 (3)° |
| Stoe IPDS II diffractometer | 2012 reflections with I > 2σ(I) |
| 19581 measured reflections | Rint = 0.035 |
| 2807 independent reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.091 | Δρmax = 0.39 e Å−3 |
| S = 0.89 | Δρmin = −0.16 e Å−3 |
| 2807 reflections | Absolute structure: ? |
| 115 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | 0.70679 (12) | 0.5276 (2) | 0.6731 (2) | 0.0525 (4) | |
| H1B | 0.6513 | 0.5582 | 0.5941 | 0.063* | |
| C2 | 0.68976 (19) | 0.5848 (2) | 0.8073 (3) | 0.0830 (7) | |
| H2A | 0.7434 | 0.5574 | 0.8868 | 0.125* | |
| H2B | 0.6336 | 0.5342 | 0.8178 | 0.125* | |
| H2C | 0.6813 | 0.6995 | 0.8034 | 0.125* | |
| C3 | 0.79173 (16) | 0.6067 (3) | 0.6497 (3) | 0.0802 (7) | |
| H3A | 0.7812 | 0.7207 | 0.6396 | 0.120* | |
| H3B | 0.8021 | 0.5645 | 0.5650 | 0.120* | |
| H3C | 0.8466 | 0.5858 | 0.7294 | 0.120* | |
| C4 | 0.61524 (11) | 0.22776 (19) | 0.69367 (17) | 0.0418 (4) | |
| H4 | 0.6119 | 0.2607 | 0.7874 | 0.050* | |
| C5 | 0.52745 (12) | 0.2872 (3) | 0.5848 (2) | 0.0653 (6) | |
| H5A | 0.5320 | 0.2652 | 0.4915 | 0.098* | |
| H5B | 0.5213 | 0.4010 | 0.5960 | 0.098* | |
| H5C | 0.4727 | 0.2333 | 0.5971 | 0.098* | |
| C6 | 0.62213 (15) | 0.0496 (2) | 0.6924 (2) | 0.0692 (6) | |
| H6A | 0.5651 | 0.0034 | 0.7039 | 0.104* | |
| H6B | 0.6759 | 0.0151 | 0.7689 | 0.104* | |
| H6C | 0.6298 | 0.0150 | 0.6037 | 0.104* | |
| C7 | 0.89734 (10) | 0.2189 (2) | 0.79953 (16) | 0.0427 (4) | |
| H7 | 0.9106 | 0.2800 | 0.7226 | 0.051* | |
| C8 | 0.96785 (13) | 0.2667 (3) | 0.9330 (2) | 0.0733 (6) | |
| H8A | 0.9625 | 0.3801 | 0.9478 | 0.110* | |
| H8B | 1.0306 | 0.2429 | 0.9282 | 0.110* | |
| H8C | 0.9566 | 0.2083 | 1.0104 | 0.110* | |
| C9 | 0.90379 (17) | 0.0463 (3) | 0.7687 (3) | 0.0834 (7) | |
| H9A | 0.8915 | −0.0166 | 0.8429 | 0.125* | |
| H9B | 0.9664 | 0.0226 | 0.7633 | 0.125* | |
| H9C | 0.8576 | 0.0206 | 0.6797 | 0.125* | |
| N1 | 0.80376 (9) | 0.26201 (16) | 0.80317 (13) | 0.0398 (3) | |
| H1A | 0.7925 | 0.2590 | 0.8840 | 0.048* | |
| O1 | 0.73426 (8) | 0.26804 (15) | 0.53446 (11) | 0.0531 (3) | |
| P1 | 0.71920 (3) | 0.31507 (5) | 0.66763 (4) | 0.03470 (12) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0490 (10) | 0.0468 (9) | 0.0619 (11) | 0.0063 (8) | 0.0167 (9) | 0.0155 (9) |
| C2 | 0.1089 (19) | 0.0465 (12) | 0.1096 (19) | 0.0121 (12) | 0.0570 (16) | −0.0108 (12) |
| C3 | 0.0785 (15) | 0.0565 (13) | 0.112 (2) | −0.0137 (11) | 0.0373 (14) | 0.0151 (12) |
| C4 | 0.0398 (8) | 0.0532 (10) | 0.0348 (8) | −0.0039 (7) | 0.0148 (7) | 0.0047 (7) |
| C5 | 0.0366 (9) | 0.0924 (16) | 0.0629 (12) | −0.0074 (9) | 0.0087 (8) | 0.0160 (11) |
| C6 | 0.0697 (13) | 0.0576 (12) | 0.0814 (15) | −0.0150 (10) | 0.0243 (12) | 0.0030 (10) |
| C7 | 0.0377 (8) | 0.0581 (11) | 0.0365 (8) | 0.0107 (7) | 0.0174 (7) | 0.0075 (7) |
| C8 | 0.0426 (10) | 0.1149 (19) | 0.0573 (12) | 0.0060 (11) | 0.0072 (9) | −0.0030 (12) |
| C9 | 0.0787 (15) | 0.0704 (15) | 0.1029 (19) | 0.0283 (12) | 0.0297 (14) | −0.0056 (13) |
| N1 | 0.0383 (7) | 0.0593 (8) | 0.0250 (6) | 0.0094 (6) | 0.0143 (5) | 0.0085 (6) |
| O1 | 0.0553 (7) | 0.0817 (9) | 0.0270 (6) | 0.0022 (6) | 0.0193 (5) | 0.0009 (5) |
| P1 | 0.03607 (19) | 0.0451 (2) | 0.02528 (19) | 0.00340 (18) | 0.01274 (14) | 0.00474 (18) |
| C1—C3 | 1.521 (3) | C6—H6A | 0.9800 |
| C1—C2 | 1.528 (3) | C6—H6B | 0.9800 |
| C1—P1 | 1.8150 (18) | C6—H6C | 0.9800 |
| C1—H1B | 1.0000 | C7—N1 | 1.4644 (19) |
| C2—H2A | 0.9800 | C7—C8 | 1.498 (3) |
| C2—H2B | 0.9800 | C7—C9 | 1.505 (3) |
| C2—H2C | 0.9800 | C7—H7 | 1.0000 |
| C3—H3A | 0.9800 | C8—H8A | 0.9800 |
| C3—H3B | 0.9800 | C8—H8B | 0.9800 |
| C3—H3C | 0.9800 | C8—H8C | 0.9800 |
| C4—C6 | 1.515 (3) | C9—H9A | 0.9800 |
| C4—C5 | 1.527 (2) | C9—H9B | 0.9800 |
| C4—P1 | 1.8175 (16) | C9—H9C | 0.9800 |
| C4—H4 | 1.0000 | N1—P1 | 1.6265 (14) |
| C5—H5A | 0.9800 | N1—H1A | 0.8800 |
| C5—H5B | 0.9800 | O1—P1 | 1.4799 (11) |
| C5—H5C | 0.9800 | ||
| C3—C1—C2 | 111.54 (18) | H6A—C6—H6B | 109.5 |
| C3—C1—P1 | 109.54 (13) | C4—C6—H6C | 109.5 |
| C2—C1—P1 | 112.84 (13) | H6A—C6—H6C | 109.5 |
| C3—C1—H1B | 107.6 | H6B—C6—H6C | 109.5 |
| C2—C1—H1B | 107.6 | N1—C7—C8 | 109.72 (14) |
| P1—C1—H1B | 107.6 | N1—C7—C9 | 111.68 (15) |
| C1—C2—H2A | 109.5 | C8—C7—C9 | 112.11 (17) |
| C1—C2—H2B | 109.5 | N1—C7—H7 | 107.7 |
| H2A—C2—H2B | 109.5 | C8—C7—H7 | 107.7 |
| C1—C2—H2C | 109.5 | C9—C7—H7 | 107.7 |
| H2A—C2—H2C | 109.5 | C7—C8—H8A | 109.5 |
| H2B—C2—H2C | 109.5 | C7—C8—H8B | 109.5 |
| C1—C3—H3A | 109.5 | H8A—C8—H8B | 109.5 |
| C1—C3—H3B | 109.5 | C7—C8—H8C | 109.5 |
| H3A—C3—H3B | 109.5 | H8A—C8—H8C | 109.5 |
| C1—C3—H3C | 109.5 | H8B—C8—H8C | 109.5 |
| H3A—C3—H3C | 109.5 | C7—C9—H9A | 109.5 |
| H3B—C3—H3C | 109.5 | C7—C9—H9B | 109.5 |
| C6—C4—C5 | 111.69 (16) | H9A—C9—H9B | 109.5 |
| C6—C4—P1 | 109.96 (12) | C7—C9—H9C | 109.5 |
| C5—C4—P1 | 110.96 (11) | H9A—C9—H9C | 109.5 |
| C6—C4—H4 | 108.0 | H9B—C9—H9C | 109.5 |
| C5—C4—H4 | 108.0 | C7—N1—P1 | 124.33 (10) |
| P1—C4—H4 | 108.0 | C7—N1—H1A | 117.8 |
| C4—C5—H5A | 109.5 | P1—N1—H1A | 117.8 |
| C4—C5—H5B | 109.5 | O1—P1—N1 | 113.17 (7) |
| H5A—C5—H5B | 109.5 | O1—P1—C1 | 109.89 (8) |
| C4—C5—H5C | 109.5 | N1—P1—C1 | 108.11 (8) |
| H5A—C5—H5C | 109.5 | O1—P1—C4 | 113.05 (8) |
| H5B—C5—H5C | 109.5 | N1—P1—C4 | 104.85 (7) |
| C4—C6—H6A | 109.5 | C1—P1—C4 | 107.44 (8) |
| C4—C6—H6B | 109.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O1i | 0.88 | 1.98 | 2.8344 (17) | 165 |
| Symmetry codes: (i) x, −y+1/2, z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O1i | 0.88 | 1.98 | 2.8344 (17) | 165 |
| Symmetry codes: (i) x, −y+1/2, z+1/2. |
This work was supported by the Leibniz-Institut für Katalyse e.V. an der Universität Rostock.
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Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany.
Aminophosphines with alkyl-substituents undergo oxidation very easily compared to their analogue aryl-substituted species. Most of the structurally characterized P,P-diorganylphosphinic amides R1R2P(O)NHR3 have a sterogenic phosphorus or nitrogen centre (Burns et al., 1997, Denmark et al., 2002, Kolodiazhnyi et al., 2003 and Francesco et al., 2010). Here we report about the structural characterization of the known compound (iPr)2P(O)N(H)iPr (Fig. 1). The P1—O1 distance is with 1.4799 (11) Å in the range of a P═O double bond. A strong intermolecular hydrogen bond N1—H1A···O1 (N1···O1 2.834 (2), H1A···O1 1.98 Å and N1—H1A···O1 165°) was observed.