N,P,P-Triisopropyl-phosphinic amide.

The title compound, C(9)H(22)NOP, was obtained by slow diffusion of oxygen into a toluene solution of (i)Pr(2)PNH(i)Pr. In the crystal, an inter-molecular N-H⋯O hydrogen bond occurs.

Related literature

For the synthesis of the starting compound (iPr)2PNHPr, see: Kuchen et al. (1990 ▶). For a similar synthesis of the title compound, see: Brück et al. (1995 ▶). For similar structures of R 2P(O)NHR in which the P atom has at least one attached alkyl substituent, see: Burns et al. (1997 ▶); Denmark & Dorow (2002 ▶); Kolodiazhnyi et al. (2003 ▶); Francesco et al. (2010 ▶).

Experimental

Crystal data

C9H22NOP

M = 191.25

Monoclinic,

a = 15.030 (3) Å

b = 8.4813 (17) Å

c = 10.071 (2) Å

β = 107.36 (3)°

V = 1225.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 195 K

0.42 × 0.26 × 0.20 mm

Data collection

Stoe IPDS II diffractometer

19581 measured reflections

2807 independent reflections

2012 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.091

S = 0.89

2807 reflections

115 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.16 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018551/yk2008sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018551/yk2008Isup2.hkl

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

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

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

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.88	1.98	2.8344 (17)	165

Symmetry code: (i) .