N,N'-Dicyclo-hexyl-N'',N''-dimethyl-phospho-ric triamide.

In the title compound, C(14)H(30)N(3)OP, both cyclo-hexyl groups adopt chair conformations with the NH unit in an equatorial position. The P atom adopts a slightly distorted tetra-hedral environment. In the (CH(3))(2)NP(O) unit, the O-P-N-C torsion angles, showing the orientations of the methyl groups with respect to the phosphoryl group, are -166.6 (3) and 34.6 (4)°. The O atom of the P=O group acts as a double hydrogen-bond acceptor and is involved in two different inter-molecular N-H⋯OP hydrogen bonds, building R(2) (2)(8) rings that are further linked into chains running parallel to the b axis.

Related literature

For the structure of a phospho­ramidate with a [(CH3)2N]P(O) unit, see: Ghadimi et al. (2009 ▶). For bond distances in related structures, see: Sabbaghi et al. (2010 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For double hydrogen-bond acceptors, see: Steiner (2002 ▶).

Experimental

Crystal data

C14H30N3OP

M = 287.38

Monoclinic,

a = 11.742 (4) Å

b = 7.712 (3) Å

c = 18.366 (6) Å

β = 102.120 (7)°

V = 1626.0 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 120 K

0.23 × 0.19 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.932, T max = 0.974

11336 measured reflections

3507 independent reflections

1873 reflections with I > 2σ(I)

R int = 0.103

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.199

S = 1.04

3507 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100287X/nc2217sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100287X/nc2217Isup2.hkl

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

C14H30N3OP	F(000) = 632
Mr = 287.38	Dx = 1.174 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1063 reflections
a = 11.742 (4) Å	θ = 2.3–26.9°
b = 7.712 (3) Å	µ = 0.17 mm−1
c = 18.366 (6) Å	T = 120 K
β = 102.120 (7)°	Prizm, colorless
V = 1626.0 (10) Å3	0.23 × 0.19 × 0.13 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3507 independent reflections
Radiation source: normal-focus sealed tube	1873 reflections with I > 2σ(I)
graphite	Rint = 0.103
φ and ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −15→14
Tmin = 0.932, Tmax = 0.974	k = −9→9
11336 measured reflections	l = −23→22

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)] = 0.072	Hydrogen site location: mixed
wR(F2) = 0.199	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.062P)2 + 2.1669P] where P = (Fo2 + 2Fc2)/3
3507 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.47 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	0.15685 (9)	0.10911 (13)	0.22176 (6)	0.0231 (3)
O1	0.2842 (2)	0.0799 (3)	0.23095 (15)	0.0261 (6)
N1	0.1077 (3)	0.2079 (4)	0.14150 (19)	0.0287 (8)
N2	0.0944 (3)	−0.0770 (4)	0.23092 (18)	0.0250 (8)
H2	0.1465	−0.1633	0.2435	0.030*
N3	0.1111 (3)	0.2411 (4)	0.27929 (18)	0.0242 (8)
H3	0.1359	0.3518	0.2819	0.029*
C1	0.1595 (4)	0.1671 (6)	0.0782 (2)	0.0385 (11)
H1A	0.1662	0.2733	0.0501	0.058*
H1B	0.1101	0.0834	0.0458	0.058*
H1C	0.2371	0.1170	0.0960	0.058*
C2	−0.0065 (4)	0.2895 (6)	0.1205 (3)	0.0371 (11)
H2A	0.0010	0.4007	0.0961	0.056*
H2B	−0.0381	0.3090	0.1652	0.056*
H2C	−0.0591	0.2135	0.0861	0.056*
C3	−0.0309 (3)	−0.1127 (5)	0.2152 (2)	0.0229 (8)
H3A	−0.0725	−0.0033	0.2230	0.027*
C4	−0.0756 (3)	−0.1728 (5)	0.1348 (2)	0.0281 (9)
H4A	−0.0616	−0.0807	0.1002	0.034*
H4B	−0.0320	−0.2774	0.1252	0.034*
C5	−0.2050 (4)	−0.2142 (6)	0.1202 (2)	0.0302 (10)
H5A	−0.2312	−0.2551	0.0682	0.036*
H5B	−0.2492	−0.1079	0.1264	0.036*
C6	−0.2297 (4)	−0.3535 (5)	0.1737 (2)	0.0299 (10)
H6A	−0.3145	−0.3766	0.1642	0.036*
H6B	−0.1899	−0.4624	0.1651	0.036*
C7	−0.1876 (3)	−0.2957 (5)	0.2534 (2)	0.0279 (9)
H7A	−0.2012	−0.3897	0.2873	0.033*
H7B	−0.2329	−0.1931	0.2631	0.033*
C8	−0.0574 (4)	−0.2497 (5)	0.2699 (2)	0.0272 (9)
H8A	−0.0113	−0.3555	0.2661	0.033*
H8B	−0.0342	−0.2049	0.3214	0.033*
C9	0.1053 (3)	0.1887 (5)	0.3554 (2)	0.0229 (9)
H9A	0.0596	0.0784	0.3517	0.027*
C10	0.0390 (4)	0.3243 (5)	0.3902 (2)	0.0295 (10)
H10A	−0.0386	0.3432	0.3576	0.035*
H10B	0.0819	0.4356	0.3947	0.035*
C11	0.0243 (4)	0.2654 (6)	0.4670 (3)	0.0362 (11)
H11A	−0.0234	0.1586	0.4621	0.043*
H11B	−0.0168	0.3563	0.4895	0.043*
C12	0.1444 (4)	0.2298 (6)	0.5181 (2)	0.0385 (11)
H12A	0.1894	0.3391	0.5268	0.046*
H12B	0.1334	0.1863	0.5669	0.046*
C13	0.2116 (4)	0.0969 (6)	0.4830 (2)	0.0362 (10)
H13A	0.1707	−0.0160	0.4797	0.043*
H13B	0.2900	0.0814	0.5150	0.043*
C14	0.2238 (3)	0.1534 (6)	0.4049 (2)	0.0298 (10)
H14A	0.2720	0.2596	0.4086	0.036*
H14B	0.2637	0.0611	0.3822	0.036*

	U11	U22	U33	U12	U13	U23
P1	0.0193 (5)	0.0217 (5)	0.0295 (6)	−0.0005 (4)	0.0079 (4)	−0.0001 (4)
O1	0.0198 (14)	0.0238 (15)	0.0363 (16)	−0.0024 (11)	0.0096 (12)	−0.0017 (12)
N1	0.028 (2)	0.0280 (19)	0.031 (2)	0.0039 (15)	0.0084 (15)	0.0020 (15)
N2	0.0175 (17)	0.0233 (18)	0.0352 (19)	0.0007 (13)	0.0077 (14)	0.0006 (14)
N3	0.0225 (18)	0.0228 (18)	0.0289 (19)	−0.0022 (13)	0.0087 (14)	−0.0016 (14)
C1	0.055 (3)	0.030 (2)	0.034 (3)	0.004 (2)	0.019 (2)	0.0054 (19)
C2	0.033 (3)	0.034 (2)	0.043 (3)	0.006 (2)	0.003 (2)	0.007 (2)
C3	0.0155 (19)	0.0207 (19)	0.033 (2)	−0.0009 (16)	0.0064 (16)	−0.0002 (17)
C4	0.029 (2)	0.027 (2)	0.031 (2)	−0.0042 (18)	0.0119 (18)	−0.0033 (18)
C5	0.026 (2)	0.036 (2)	0.029 (2)	−0.0036 (18)	0.0054 (18)	−0.0019 (18)
C6	0.021 (2)	0.029 (2)	0.041 (3)	−0.0014 (17)	0.0086 (18)	−0.0020 (19)
C7	0.024 (2)	0.025 (2)	0.038 (2)	−0.0022 (17)	0.0133 (18)	0.0024 (18)
C8	0.026 (2)	0.025 (2)	0.031 (2)	0.0017 (17)	0.0058 (17)	0.0008 (17)
C9	0.019 (2)	0.023 (2)	0.029 (2)	−0.0053 (16)	0.0085 (16)	−0.0014 (17)
C10	0.028 (2)	0.026 (2)	0.039 (2)	−0.0008 (18)	0.0164 (19)	0.0023 (18)
C11	0.038 (3)	0.036 (3)	0.041 (3)	0.000 (2)	0.020 (2)	−0.001 (2)
C12	0.046 (3)	0.045 (3)	0.024 (2)	−0.007 (2)	0.006 (2)	−0.002 (2)
C13	0.031 (2)	0.041 (3)	0.036 (2)	−0.005 (2)	0.0048 (19)	0.006 (2)
C14	0.024 (2)	0.031 (2)	0.035 (2)	−0.0026 (17)	0.0082 (18)	0.0004 (18)

P1—O1	1.486 (3)	C6—C7	1.511 (6)
P1—N2	1.636 (3)	C6—H6A	0.9900
P1—N3	1.637 (3)	C6—H6B	0.9900
P1—N1	1.652 (4)	C7—C8	1.536 (6)
N1—C2	1.457 (5)	C7—H7A	0.9900
N1—C1	1.456 (5)	C7—H7B	0.9900
N2—C3	1.465 (5)	C8—H8A	0.9900
N2—H2	0.9000	C8—H8B	0.9900
N3—C9	1.471 (5)	C9—C14	1.518 (5)
N3—H3	0.9000	C9—C10	1.522 (5)
C1—H1A	0.9800	C9—H9A	1.0000
C1—H1B	0.9800	C10—C11	1.526 (6)
C1—H1C	0.9800	C10—H10A	0.9900
C2—H2A	0.9800	C10—H10B	0.9900
C2—H2B	0.9800	C11—C12	1.545 (6)
C2—H2C	0.9800	C11—H11A	0.9900
C3—C4	1.532 (5)	C11—H11B	0.9900
C3—C8	1.534 (5)	C12—C13	1.518 (6)
C3—H3A	1.0000	C12—H12A	0.9900
C4—C5	1.521 (6)	C12—H12B	0.9900
C4—H4A	0.9900	C13—C14	1.535 (6)
C4—H4B	0.9900	C13—H13A	0.9900
C5—C6	1.524 (6)	C13—H13B	0.9900
C5—H5A	0.9900	C14—H14A	0.9900
C5—H5B	0.9900	C14—H14B	0.9900
O1—P1—N2	108.49 (16)	H6A—C6—H6B	108.1
O1—P1—N3	118.64 (16)	C6—C7—C8	111.7 (3)
N2—P1—N3	105.33 (17)	C6—C7—H7A	109.3
O1—P1—N1	109.04 (17)	C8—C7—H7A	109.3
N2—P1—N1	114.59 (17)	C6—C7—H7B	109.3
N3—P1—N1	100.87 (17)	C8—C7—H7B	109.3
C2—N1—C1	113.4 (3)	H7A—C7—H7B	108.0
C2—N1—P1	124.4 (3)	C7—C8—C3	111.1 (3)
C1—N1—P1	119.1 (3)	C7—C8—H8A	109.4
C3—N2—P1	126.7 (3)	C3—C8—H8A	109.4
C3—N2—H2	120.8	C7—C8—H8B	109.4
P1—N2—H2	112.3	C3—C8—H8B	109.4
C9—N3—P1	122.0 (3)	H8A—C8—H8B	108.0
C9—N3—H3	106.8	N3—C9—C14	113.4 (3)
P1—N3—H3	118.5	N3—C9—C10	109.9 (3)
N1—C1—H1A	109.5	C14—C9—C10	111.0 (3)
N1—C1—H1B	109.5	N3—C9—H9A	107.4
H1A—C1—H1B	109.5	C14—C9—H9A	107.4
N1—C1—H1C	109.5	C10—C9—H9A	107.4
H1A—C1—H1C	109.5	C9—C10—C11	110.5 (3)
H1B—C1—H1C	109.5	C9—C10—H10A	109.6
N1—C2—H2A	109.5	C11—C10—H10A	109.6
N1—C2—H2B	109.5	C9—C10—H10B	109.6
H2A—C2—H2B	109.5	C11—C10—H10B	109.6
N1—C2—H2C	109.5	H10A—C10—H10B	108.1
H2A—C2—H2C	109.5	C10—C11—C12	110.5 (3)
H2B—C2—H2C	109.5	C10—C11—H11A	109.6
N2—C3—C4	111.9 (3)	C12—C11—H11A	109.6
N2—C3—C8	109.5 (3)	C10—C11—H11B	109.6
C4—C3—C8	110.3 (3)	C12—C11—H11B	109.6
N2—C3—H3A	108.3	H11A—C11—H11B	108.1
C4—C3—H3A	108.3	C13—C12—C11	110.5 (4)
C8—C3—H3A	108.3	C13—C12—H12A	109.5
C5—C4—C3	111.2 (3)	C11—C12—H12A	109.5
C5—C4—H4A	109.4	C13—C12—H12B	109.5
C3—C4—H4A	109.4	C11—C12—H12B	109.5
C5—C4—H4B	109.4	H12A—C12—H12B	108.1
C3—C4—H4B	109.4	C12—C13—C14	111.4 (4)
H4A—C4—H4B	108.0	C12—C13—H13A	109.3
C4—C5—C6	110.6 (3)	C14—C13—H13A	109.3
C4—C5—H5A	109.5	C12—C13—H13B	109.3
C6—C5—H5A	109.5	C14—C13—H13B	109.3
C4—C5—H5B	109.5	H13A—C13—H13B	108.0
C6—C5—H5B	109.5	C9—C14—C13	110.9 (3)
H5A—C5—H5B	108.1	C9—C14—H14A	109.5
C7—C6—C5	110.4 (3)	C13—C14—H14A	109.5
C7—C6—H6A	109.6	C9—C14—H14B	109.5
C5—C6—H6A	109.6	C13—C14—H14B	109.5
C7—C6—H6B	109.6	H14A—C14—H14B	108.1
C5—C6—H6B	109.6
O1—P1—N1—C2	−166.6 (3)	C3—C4—C5—C6	−58.0 (4)
N2—P1—N1—C2	71.6 (4)	C4—C5—C6—C7	57.8 (4)
N3—P1—N1—C2	−40.9 (4)	C5—C6—C7—C8	−56.5 (4)
O1—P1—N1—C1	34.6 (4)	C6—C7—C8—C3	55.2 (4)
N2—P1—N1—C1	−87.2 (3)	N2—C3—C8—C7	−177.9 (3)
N3—P1—N1—C1	160.2 (3)	C4—C3—C8—C7	−54.3 (4)
O1—P1—N2—C3	−170.3 (3)	P1—N3—C9—C14	65.7 (4)
N3—P1—N2—C3	61.7 (3)	P1—N3—C9—C10	−169.4 (3)
N1—P1—N2—C3	−48.2 (4)	N3—C9—C10—C11	175.8 (3)
O1—P1—N3—C9	−77.8 (3)	C14—C9—C10—C11	−57.9 (4)
N2—P1—N3—C9	43.8 (3)	C9—C10—C11—C12	57.5 (5)
N1—P1—N3—C9	163.3 (3)	C10—C11—C12—C13	−56.5 (5)
P1—N2—C3—C4	91.1 (4)	C11—C12—C13—C14	55.4 (5)
P1—N2—C3—C8	−146.3 (3)	N3—C9—C14—C13	−179.2 (3)
N2—C3—C4—C5	178.3 (3)	C10—C9—C14—C13	56.6 (4)
C8—C3—C4—C5	56.1 (4)	C12—C13—C14—C9	−55.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90	2.16	3.017 (4)	160
N3—H3···O1ii	0.90	2.03	2.911 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.90	2.16	3.017 (4)	160
N3—H3⋯O1ii	0.90	2.03	2.911 (4)	165

Symmetry codes: (i) ; (ii) .