p-Tolyl bis-(cyclo-hexyl-amido)-phosphinate.

The P atom in the title mol-ecule, C(19)H(31)N(2)O(2)P, is in a distorted tetra-hedral configuration with the bond angles in the range 101.48 (10)-118.58 (9)°. The N-H units have a syn orientation with respect to one another. In the crystal, mol-ecules are connected via two different inter-molecular N-H⋯O(P) hydrogen bonds into chains along the a axis in which the O atom of the P=O group acts as a double acceptor.

Related literature

For background to phospho­ramidate compounds, see: Pourayoubi et al. (2011 ▶). For bond lengths in related structures, see: Sabbaghi et al. (2011 ▶); pan class="Species">Rudd et al. (1996 ▶). For double class="Chemical">pan class="Chemical">hydrogen-bond acceptors, see: Steiner (2002 ▶).

Experimental

Crystal data

pan class="Chemical">C19H31N2O2P

M = 350.43

Monoclinic,

a = 9.131 (5) Å

b = 19.333 (5) Å

c = 11.291 (5) Å

β = 99.247 (5)°

V = 1967.3 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 291 K

0.38 × 0.12 × 0.08 mm

Data collection

Stoe IPDS II image plate diffractometer

Absorption correction: multi-scan [MULABS (Blessing, 1995 ▶) in PLATON (Spek, 2009 ▶)] T min = 0.992, T max = 1.000

14835 measured reflections

5296 independent reflections

1925 reflections with I > 2σ(I)

R int = 0.091

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.090

S = 0.76

5296 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.26 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶) and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029722/lh5287sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029722/lh5287Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029722/lh5287Isup3.cml

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

C19H31N2O2P	F(000) = 760
Mr = 350.43	Dx = 1.183 Mg m−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yab	Cell parameters from 3912 reflections
a = 9.131 (5) Å	θ = 1.8–29.5°
b = 19.333 (5) Å	µ = 0.15 mm−1
c = 11.291 (5) Å	T = 291 K
β = 99.247 (5)°	Block, colourless
V = 1967.3 (15) Å3	0.38 × 0.12 × 0.08 mm
Z = 4

Stoe IPDS II image plate diffractometer	5296 independent reflections
Radiation source: fine-focus sealed tube	1925 reflections with I > 2σ(I)
graphite	Rint = 0.091
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.2°, θmin = 1.8°
ω scans	h = −12→9
Absorption correction: multi-scan [MULABS (Blessing, 1995) in PLATON (Spek, 2009)]	k = −22→26
Tmin = 0.992, Tmax = 1.000	l = −15→15
14835 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 0.76	w = 1/[σ2(Fo2) + (0.0255P)2] where P = (Fo2 + 2Fc2)/3
5296 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.26 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
P1	0.71746 (8)	0.80003 (4)	0.50141 (5)	0.03970 (16)
O1	0.87988 (16)	0.79943 (9)	0.51391 (11)	0.0481 (4)
O2	0.66002 (18)	0.87739 (8)	0.46763 (13)	0.0530 (5)
N1	0.6357 (2)	0.74705 (11)	0.40180 (15)	0.0540 (6)
H1	0.5695	0.7286	0.4204	0.065*
N2	0.6418 (2)	0.78465 (10)	0.61857 (13)	0.0488 (6)
H2	0.5753	0.7613	0.6076	0.059*
C1	0.7075 (3)	0.71015 (13)	0.31259 (16)	0.0433 (6)
H1A	0.7944	0.7370	0.2994	0.052*
C2	0.7592 (3)	0.63929 (14)	0.3529 (2)	0.0637 (8)
H2A	0.6753	0.6125	0.3700	0.076*
H2B	0.8301	0.6429	0.4264	0.076*
C3	0.8310 (4)	0.60189 (16)	0.2589 (2)	0.0779 (9)
H3A	0.8596	0.5557	0.2870	0.093*
H3B	0.9199	0.6264	0.2465	0.093*
C4	0.7244 (3)	0.59729 (16)	0.1408 (2)	0.0749 (9)
H4A	0.7738	0.5756	0.0806	0.090*
H4B	0.6397	0.5690	0.1513	0.090*
C5	0.6727 (4)	0.66822 (17)	0.0996 (2)	0.0755 (9)
H5A	0.6010	0.6644	0.0266	0.091*
H5B	0.7565	0.6947	0.0813	0.091*
C6	0.6017 (3)	0.70671 (14)	0.19495 (17)	0.0579 (7)
H6A	0.5753	0.7532	0.1672	0.070*
H6B	0.5116	0.6831	0.2070	0.070*
C7	0.6472 (3)	0.83281 (12)	0.71992 (17)	0.0434 (6)
H7A	0.7147	0.8706	0.7074	0.052*
C8	0.7099 (3)	0.79764 (16)	0.83611 (18)	0.0739 (9)
H8A	0.8094	0.7815	0.8318	0.089*
H8B	0.6494	0.7577	0.8473	0.089*
C9	0.7148 (4)	0.84609 (17)	0.94366 (19)	0.0768 (10)
H9A	0.7512	0.8210	1.0168	0.092*
H9B	0.7830	0.8838	0.9366	0.092*
C10	0.5655 (4)	0.87468 (17)	0.9507 (2)	0.0772 (10)
H10A	0.5721	0.9065	1.0178	0.093*
H10B	0.4990	0.8374	0.9642	0.093*
C11	0.5044 (4)	0.91182 (17)	0.8365 (2)	0.0913 (11)
H11A	0.5660	0.9517	0.8271	0.110*
H11B	0.4051	0.9282	0.8410	0.110*
C12	0.4996 (3)	0.86385 (16)	0.7272 (2)	0.0715 (9)
H12A	0.4285	0.8271	0.7321	0.086*
H12B	0.4662	0.8900	0.6545	0.086*
C13	0.7349 (3)	0.92389 (13)	0.40431 (19)	0.0448 (6)
C14	0.7785 (4)	0.98514 (16)	0.4565 (2)	0.0709 (9)
H14A	0.7614	0.9946	0.5338	0.085*
C15	0.8477 (4)	1.03306 (16)	0.3956 (2)	0.0788 (10)
H15A	0.8768	1.0749	0.4327	0.095*
C16	0.8753 (3)	1.02153 (15)	0.2822 (2)	0.0572 (7)
C17	0.8292 (3)	0.95964 (15)	0.2303 (2)	0.0596 (8)
H17A	0.8452	0.9504	0.1526	0.072*
C18	0.7597 (3)	0.91060 (14)	0.2906 (2)	0.0566 (7)
H18A	0.7298	0.8687	0.2538	0.068*
C19	0.9524 (4)	1.07473 (16)	0.2168 (3)	0.0979 (12)
H19A	1.0489	1.0841	0.2614	0.147*
H19B	0.8950	1.1166	0.2084	0.147*
H19C	0.9623	1.0575	0.1388	0.147*

	U11	U22	U33	U12	U13	U23
P1	0.0361 (3)	0.0466 (4)	0.0374 (3)	0.0011 (4)	0.0089 (2)	−0.0014 (3)
O1	0.0345 (10)	0.0549 (12)	0.0549 (9)	−0.0006 (10)	0.0065 (7)	0.0005 (8)
O2	0.0502 (12)	0.0530 (12)	0.0600 (10)	0.0080 (10)	0.0210 (8)	0.0112 (8)
N1	0.0438 (13)	0.0734 (16)	0.0488 (10)	−0.0117 (12)	0.0196 (9)	−0.0200 (10)
N2	0.0561 (13)	0.0520 (15)	0.0416 (9)	−0.0139 (12)	0.0182 (9)	−0.0067 (9)
C1	0.0433 (14)	0.0487 (18)	0.0403 (11)	−0.0051 (14)	0.0141 (10)	−0.0057 (11)
C2	0.073 (2)	0.066 (2)	0.0506 (14)	0.0140 (18)	0.0063 (13)	0.0064 (14)
C3	0.083 (3)	0.067 (2)	0.084 (2)	0.029 (2)	0.0128 (17)	−0.0021 (16)
C4	0.081 (2)	0.071 (2)	0.0782 (19)	−0.003 (2)	0.0282 (17)	−0.0296 (17)
C5	0.092 (2)	0.088 (3)	0.0452 (14)	0.011 (2)	0.0089 (14)	−0.0147 (15)
C6	0.0702 (18)	0.0572 (18)	0.0452 (12)	0.0103 (17)	0.0056 (12)	−0.0002 (13)
C7	0.0493 (17)	0.0437 (16)	0.0391 (12)	−0.0108 (13)	0.0127 (11)	−0.0037 (11)
C8	0.084 (2)	0.088 (2)	0.0474 (14)	0.028 (2)	0.0033 (13)	−0.0066 (15)
C9	0.085 (2)	0.101 (3)	0.0421 (14)	0.013 (2)	0.0043 (14)	−0.0095 (14)
C10	0.083 (2)	0.100 (3)	0.0533 (16)	−0.006 (2)	0.0253 (15)	−0.0225 (15)
C11	0.092 (3)	0.107 (3)	0.0727 (19)	0.041 (2)	0.0048 (17)	−0.0266 (18)
C12	0.065 (2)	0.094 (2)	0.0522 (15)	0.0257 (19)	−0.0001 (13)	−0.0125 (15)
C13	0.0411 (16)	0.0481 (18)	0.0457 (13)	0.0065 (14)	0.0084 (11)	0.0076 (12)
C14	0.110 (3)	0.058 (2)	0.0485 (15)	−0.009 (2)	0.0244 (16)	−0.0067 (14)
C15	0.109 (3)	0.058 (2)	0.0689 (18)	−0.021 (2)	0.0120 (18)	−0.0091 (15)
C16	0.0531 (19)	0.057 (2)	0.0602 (16)	−0.0057 (17)	0.0047 (13)	0.0123 (15)
C17	0.067 (2)	0.068 (2)	0.0466 (14)	−0.0009 (17)	0.0162 (13)	0.0010 (14)
C18	0.0625 (19)	0.0537 (19)	0.0560 (15)	−0.0107 (16)	0.0168 (13)	−0.0086 (13)
C19	0.102 (3)	0.089 (3)	0.103 (2)	−0.028 (2)	0.018 (2)	0.0294 (19)

P1—O1	1.4670 (17)	C8—C9	1.528 (3)
P1—O2	1.6105 (17)	C8—H8A	0.9700
P1—N1	1.6131 (19)	C8—H8B	0.9700
P1—N2	1.6152 (18)	C9—C10	1.486 (4)
O2—C13	1.394 (3)	C9—H9A	0.9700
N1—C1	1.472 (3)	C9—H9B	0.9700
N1—H1	0.7593	C10—C11	1.503 (4)
N2—C7	1.470 (3)	C10—H10A	0.9700
N2—H2	0.7510	C10—H10B	0.9700
C1—C2	1.496 (3)	C11—C12	1.539 (3)
C1—C6	1.513 (3)	C11—H11A	0.9700
C1—H1A	0.9800	C11—H11B	0.9700
C2—C3	1.517 (3)	C12—H12A	0.9700
C2—H2A	0.9700	C12—H12B	0.9700
C2—H2B	0.9700	C13—C14	1.354 (3)
C3—C4	1.522 (3)	C13—C18	1.364 (3)
C3—H3A	0.9700	C14—C15	1.367 (4)
C3—H3B	0.9700	C14—H14A	0.9300
C4—C5	1.500 (4)	C15—C16	1.362 (3)
C4—H4A	0.9700	C15—H15A	0.9300
C4—H4B	0.9700	C16—C17	1.369 (3)
C5—C6	1.536 (3)	C16—C19	1.505 (4)
C5—H5A	0.9700	C17—C18	1.380 (3)
C5—H5B	0.9700	C17—H17A	0.9300
C6—H6A	0.9700	C18—H18A	0.9300
C6—H6B	0.9700	C19—H19A	0.9600
C7—C12	1.490 (3)	C19—H19B	0.9600
C7—C8	1.506 (3)	C19—H19C	0.9600
C7—H7A	0.9800
O1—P1—O2	108.41 (10)	C7—C8—C9	112.0 (2)
O1—P1—N1	114.19 (10)	C7—C8—H8A	109.2
O2—P1—N1	109.13 (10)	C9—C8—H8A	109.2
O1—P1—N2	118.58 (9)	C7—C8—H8B	109.2
O2—P1—N2	101.48 (10)	C9—C8—H8B	109.2
N1—P1—N2	104.07 (11)	H8A—C8—H8B	107.9
C13—O2—P1	123.52 (15)	C10—C9—C8	111.1 (2)
C1—N1—P1	125.28 (16)	C10—C9—H9A	109.4
C1—N1—H1	115.1	C8—C9—H9A	109.4
P1—N1—H1	113.9	C10—C9—H9B	109.4
C7—N2—P1	123.76 (16)	C8—C9—H9B	109.4
C7—N2—H2	115.8	H9A—C9—H9B	108.0
P1—N2—H2	114.6	C9—C10—C11	110.4 (2)
N1—C1—C2	112.93 (18)	C9—C10—H10A	109.6
N1—C1—C6	109.3 (2)	C11—C10—H10A	109.6
C2—C1—C6	110.6 (2)	C9—C10—H10B	109.6
N1—C1—H1A	107.9	C11—C10—H10B	109.6
C2—C1—H1A	107.9	H10A—C10—H10B	108.1
C6—C1—H1A	107.9	C10—C11—C12	111.1 (3)
C1—C2—C3	112.0 (2)	C10—C11—H11A	109.4
C1—C2—H2A	109.2	C12—C11—H11A	109.4
C3—C2—H2A	109.2	C10—C11—H11B	109.4
C1—C2—H2B	109.2	C12—C11—H11B	109.4
C3—C2—H2B	109.2	H11A—C11—H11B	108.0
H2A—C2—H2B	107.9	C7—C12—C11	112.2 (2)
C2—C3—C4	110.7 (2)	C7—C12—H12A	109.2
C2—C3—H3A	109.5	C11—C12—H12A	109.2
C4—C3—H3A	109.5	C7—C12—H12B	109.2
C2—C3—H3B	109.5	C11—C12—H12B	109.2
C4—C3—H3B	109.5	H12A—C12—H12B	107.9
H3A—C3—H3B	108.1	C14—C13—C18	119.5 (2)
C5—C4—C3	110.1 (2)	C14—C13—O2	118.4 (2)
C5—C4—H4A	109.6	C18—C13—O2	122.0 (2)
C3—C4—H4A	109.6	C13—C14—C15	120.1 (2)
C5—C4—H4B	109.6	C13—C14—H14A	120.0
C3—C4—H4B	109.6	C15—C14—H14A	120.0
H4A—C4—H4B	108.2	C16—C15—C14	122.1 (3)
C4—C5—C6	111.9 (2)	C16—C15—H15A	118.9
C4—C5—H5A	109.2	C14—C15—H15A	118.9
C6—C5—H5A	109.2	C15—C16—C17	117.1 (3)
C4—C5—H5B	109.2	C15—C16—C19	121.4 (3)
C6—C5—H5B	109.2	C17—C16—C19	121.5 (3)
H5A—C5—H5B	107.9	C16—C17—C18	121.6 (2)
C1—C6—C5	110.8 (2)	C16—C17—H17A	119.2
C1—C6—H6A	109.5	C18—C17—H17A	119.2
C5—C6—H6A	109.5	C13—C18—C17	119.6 (2)
C1—C6—H6B	109.5	C13—C18—H18A	120.2
C5—C6—H6B	109.5	C17—C18—H18A	120.2
H6A—C6—H6B	108.1	C16—C19—H19A	109.5
N2—C7—C12	112.36 (19)	C16—C19—H19B	109.5
N2—C7—C8	110.7 (2)	H19A—C19—H19B	109.5
C12—C7—C8	110.73 (19)	C16—C19—H19C	109.5
N2—C7—H7A	107.6	H19A—C19—H19C	109.5
C12—C7—H7A	107.6	H19B—C19—H19C	109.5
C8—C7—H7A	107.6
O1—P1—O2—C13	29.02 (19)	N2—C7—C8—C9	−179.1 (2)
N1—P1—O2—C13	−95.91 (19)	C12—C7—C8—C9	−53.9 (3)
N2—P1—O2—C13	154.63 (17)	C7—C8—C9—C10	56.4 (3)
O1—P1—N1—C1	−11.6 (2)	C8—C9—C10—C11	−57.2 (3)
O2—P1—N1—C1	109.9 (2)	C9—C10—C11—C12	56.4 (3)
N2—P1—N1—C1	−142.37 (19)	N2—C7—C12—C11	177.5 (2)
O1—P1—N2—C7	70.6 (2)	C8—C7—C12—C11	53.2 (3)
O2—P1—N2—C7	−48.0 (2)	C10—C11—C12—C7	−55.1 (4)
N1—P1—N2—C7	−161.28 (18)	P1—O2—C13—C14	−121.7 (2)
P1—N1—C1—C2	94.3 (2)	P1—O2—C13—C18	61.1 (3)
P1—N1—C1—C6	−142.1 (2)	C18—C13—C14—C15	−0.4 (4)
N1—C1—C2—C3	179.3 (2)	O2—C13—C14—C15	−177.7 (3)
C6—C1—C2—C3	56.4 (3)	C13—C14—C15—C16	−0.1 (5)
C1—C2—C3—C4	−57.1 (3)	C14—C15—C16—C17	0.7 (5)
C2—C3—C4—C5	56.1 (3)	C14—C15—C16—C19	−179.6 (3)
C3—C4—C5—C6	−55.9 (3)	C15—C16—C17—C18	−0.9 (4)
N1—C1—C6—C5	−179.8 (2)	C19—C16—C17—C18	179.5 (3)
C2—C1—C6—C5	−54.8 (3)	C14—C13—C18—C17	0.2 (4)
C4—C5—C6—C1	55.7 (3)	O2—C13—C18—C17	177.4 (2)
P1—N2—C7—C12	110.5 (2)	C16—C17—C18—C13	0.4 (4)
P1—N2—C7—C8	−125.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.76	2.23	2.969 (3)	163.
N2—H2···O1i	0.75	2.25	2.975 (3)	162.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.76	2.23	2.969 (3)	163
N2—H2⋯O1i	0.75	2.25	2.975 (3)	162

Symmetry code: (i) .