N-Benzoyl-N',N''-dicyclo-hexyl-phospho-ric triamide.

In the title compound, C(19)H(30)N(3)O(2)P, the central P atom has a distorted tetra-hedral configuration. The N atoms in both cyclo-hexyl-amide moieties exhibit a slight deviation [0.32 (7) and 0.44 (6) Å] from planarity, while the benzoyl-amide N atom is planar [0.11 (3) Å]. In the crystal, mol-ecules are linked via N-H⋯O(P) and N-H⋯O(C) hydrogen bonds, forming R(2) (2)(10) rings within linear arrangements parallel to the b axis.

Related literature

For the synthesis and a spectroscopic study of title compound, see: Gholivand et al. (2006 ▶). For bond lengths in related structures, see: Sabbaghi et al. (2010 ▶); Rudd et al. (1996 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H30N3O2P

M = 363.43

Monoclinic,

a = 20.9904 (17) Å

b = 5.1503 (2) Å

c = 21.1125 (18) Å

β = 121.955 (11)°

V = 1936.5 (2) Å3

Z = 4

Cu Kα radiation

μ = 1.39 mm−1

T = 293 K

0.28 × 0.05 × 0.01 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.978, T max = 1.000

2758 measured reflections

2758 independent reflections

2294 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.122

S = 1.05

2758 reflections

239 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 908 Friedel pairs

Flack parameter: 0.11 (4)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016679/ld2010sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016679/ld2010Isup2.hkl

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

C19H30N3O2P	F(000) = 784
Mr = 363.43	Dx = 1.247 Mg m−3
Monoclinic, Cc	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: C -2yc	Cell parameters from 1733 reflections
a = 20.9904 (17) Å	θ = 4.2–70.2°
b = 5.1503 (2) Å	µ = 1.39 mm−1
c = 21.1125 (18) Å	T = 293 K
β = 121.955 (11)°	Prismatic, colorless
V = 1936.5 (2) Å3	0.28 × 0.05 × 0.01 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2758 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2294 reflections with I > 2σ(I)
graphite	Rint = 0.064
Detector resolution: 10.2673 pixels mm-1	θmax = 70.3°, θmin = 4.8°
ω scans	h = −24→24
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = 0→6
Tmin = 0.978, Tmax = 1.000	l = −25→25
2758 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0489P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2758 reflections	Δρmax = 0.46 e Å−3
239 parameters	Δρmin = −0.18 e Å−3
2 restraints	Absolute structure: Flack (1983), 908 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.11 (4)

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	0.00072 (6)	0.2629 (2)	0.30701 (6)	0.0403 (2)
O2	−0.02706 (18)	0.5292 (5)	0.30029 (19)	0.0504 (8)
O3	0.11281 (18)	−0.1251 (6)	0.3206 (2)	0.0578 (9)
N4	0.0865 (2)	0.3029 (6)	0.3150 (2)	0.0435 (8)
N5	−0.0520 (2)	0.0724 (7)	0.2376 (2)	0.0438 (9)
N6	0.0150 (2)	0.0959 (8)	0.3781 (2)	0.0458 (9)
C7	0.1289 (2)	0.1008 (8)	0.3169 (2)	0.0398 (9)
C8	0.1958 (2)	0.1615 (7)	0.3117 (2)	0.0401 (9)
C9	0.1990 (3)	0.3714 (9)	0.2727 (3)	0.0490 (11)
H9	0.1598	0.4905	0.2518	0.059*
C10	0.2585 (3)	0.4083 (11)	0.2640 (3)	0.0616 (13)
H10	0.2590	0.5492	0.2367	0.074*
C11	0.3180 (3)	0.2347 (12)	0.2961 (3)	0.0677 (14)
H11	0.3587	0.2600	0.2907	0.081*
C12	0.3169 (3)	0.0239 (12)	0.3362 (3)	0.0722 (16)
H12	0.3569	−0.0923	0.3577	0.087*
C13	0.2559 (3)	−0.0130 (10)	0.3440 (3)	0.0533 (12)
H13	0.2549	−0.1546	0.3708	0.064*
C14	−0.0945 (2)	0.1484 (9)	0.1595 (2)	0.0451 (10)
H14	−0.1203	0.3120	0.1554	0.054*
C15	−0.1535 (3)	−0.0560 (13)	0.1154 (3)	0.0727 (17)
H15A	−0.1872	−0.0665	0.1336	0.087*
H15B	−0.1292	−0.2234	0.1235	0.087*
C16	−0.1994 (3)	0.0014 (16)	0.0314 (3)	0.0846 (19)
H16A	−0.2337	−0.1413	0.0055	0.102*
H16B	−0.2290	0.1571	0.0225	0.102*
C17	−0.1502 (3)	0.0381 (11)	0.0011 (3)	0.0638 (13)
H17B	−0.1806	0.0862	−0.0511	0.077*
H17A	−0.1251	−0.1241	0.0045	0.077*
C18	−0.0922 (4)	0.2463 (12)	0.0436 (4)	0.0774 (17)
H18A	−0.1172	0.4125	0.0352	0.093*
H18B	−0.0589	0.2579	0.0250	0.093*
C19	−0.0464 (3)	0.1896 (13)	0.1269 (3)	0.0683 (16)
H19A	−0.0162	0.0356	0.1356	0.082*
H19B	−0.0124	0.3335	0.1525	0.082*
C20	0.0677 (2)	0.1637 (8)	0.4557 (2)	0.0426 (9)
H20	0.0962	0.3151	0.4562	0.051*
C21	0.1229 (3)	−0.0486 (12)	0.4978 (3)	0.0685 (15)
H21A	0.1533	−0.0758	0.4763	0.082*
H21B	0.0956	−0.2081	0.4916	0.082*
C22	0.1746 (3)	0.0067 (15)	0.5810 (3)	0.0805 (19)
H22A	0.2054	−0.1448	0.6055	0.097*
H22B	0.2077	0.1498	0.5878	0.097*
C23	0.1303 (3)	0.0742 (10)	0.6167 (3)	0.0650 (14)
H23B	0.1019	−0.0762	0.6155	0.078*
H23A	0.1646	0.1218	0.6685	0.078*
C24	0.0777 (4)	0.2951 (13)	0.5762 (3)	0.0771 (18)
H24A	0.1068	0.4505	0.5829	0.093*
H24B	0.0477	0.3271	0.5979	0.093*
C25	0.0261 (3)	0.2433 (12)	0.4937 (3)	0.0654 (15)
H25A	−0.0029	0.3987	0.4697	0.078*
H25B	−0.0088	0.1066	0.4868	0.078*
H4	0.1046 (19)	0.457 (7)	0.3124 (19)	0.015 (8)*
H6	0.014 (3)	−0.052 (9)	0.371 (3)	0.037 (13)*
H5	−0.038 (3)	−0.067 (11)	0.248 (3)	0.062 (17)*

	U11	U22	U33	U12	U13	U23
P1	0.0447 (5)	0.0336 (4)	0.0472 (5)	0.0016 (5)	0.0276 (4)	0.0017 (5)
O2	0.0546 (17)	0.0351 (15)	0.071 (2)	0.0019 (13)	0.0401 (17)	0.0037 (14)
O3	0.061 (2)	0.0334 (17)	0.089 (3)	0.0009 (14)	0.047 (2)	0.0017 (15)
N4	0.0453 (19)	0.0326 (18)	0.060 (2)	0.0006 (15)	0.0333 (18)	−0.0008 (15)
N5	0.048 (2)	0.035 (2)	0.047 (2)	0.0003 (16)	0.0244 (18)	0.0047 (16)
N6	0.054 (2)	0.044 (2)	0.046 (2)	−0.0048 (18)	0.0301 (19)	−0.0002 (17)
C7	0.0389 (19)	0.036 (2)	0.045 (2)	0.0004 (17)	0.0228 (18)	0.0000 (17)
C8	0.041 (2)	0.0367 (19)	0.042 (2)	0.0018 (17)	0.0213 (18)	−0.0041 (17)
C9	0.052 (3)	0.045 (2)	0.059 (3)	0.002 (2)	0.035 (2)	−0.003 (2)
C10	0.068 (3)	0.062 (3)	0.076 (3)	−0.003 (3)	0.053 (3)	−0.003 (3)
C11	0.055 (3)	0.074 (4)	0.091 (4)	−0.011 (3)	0.050 (3)	−0.019 (3)
C12	0.037 (3)	0.076 (4)	0.091 (4)	0.011 (2)	0.026 (3)	−0.016 (3)
C13	0.046 (2)	0.049 (3)	0.057 (3)	0.006 (2)	0.022 (2)	−0.002 (2)
C14	0.048 (2)	0.042 (2)	0.045 (3)	0.0027 (19)	0.024 (2)	0.0002 (19)
C15	0.064 (3)	0.103 (5)	0.050 (3)	−0.034 (3)	0.030 (3)	−0.006 (3)
C16	0.059 (3)	0.116 (5)	0.064 (4)	−0.015 (3)	0.023 (3)	−0.008 (4)
C17	0.079 (3)	0.057 (3)	0.052 (3)	0.003 (3)	0.032 (3)	0.004 (2)
C18	0.107 (4)	0.070 (4)	0.067 (4)	−0.019 (4)	0.054 (4)	−0.003 (3)
C19	0.060 (3)	0.091 (4)	0.056 (3)	−0.024 (3)	0.033 (3)	0.001 (3)
C20	0.045 (2)	0.041 (2)	0.045 (2)	0.0004 (18)	0.025 (2)	0.0032 (18)
C21	0.074 (3)	0.077 (4)	0.057 (3)	0.027 (3)	0.037 (3)	0.010 (3)
C22	0.065 (3)	0.114 (5)	0.051 (4)	0.028 (4)	0.022 (3)	0.018 (3)
C23	0.083 (4)	0.055 (3)	0.053 (3)	−0.001 (3)	0.034 (3)	0.004 (2)
C24	0.102 (5)	0.075 (4)	0.056 (3)	0.017 (4)	0.043 (3)	0.000 (3)
C25	0.071 (3)	0.078 (4)	0.057 (3)	0.023 (3)	0.040 (3)	0.006 (3)

P1—O2	1.468 (3)	C16—C17	1.487 (8)
P1—N6	1.615 (4)	C16—H16A	0.9700
P1—N5	1.618 (4)	C16—H16B	0.9700
P1—N4	1.730 (4)	C17—C18	1.509 (8)
O3—C7	1.225 (5)	C17—H17B	0.9700
N4—C7	1.356 (5)	C17—H17A	0.9700
N4—H4	0.90 (4)	C18—C19	1.521 (9)
N5—C14	1.454 (6)	C18—H18A	0.9700
N5—H5	0.77 (5)	C18—H18B	0.9700
N6—C20	1.453 (6)	C19—H19A	0.9700
N6—H6	0.78 (4)	C19—H19B	0.9700
C7—C8	1.499 (6)	C20—C21	1.496 (7)
C8—C9	1.382 (6)	C20—C25	1.521 (6)
C8—C13	1.397 (6)	C20—H20	0.9800
C9—C10	1.366 (7)	C21—C22	1.525 (8)
C9—H9	0.9300	C21—H21A	0.9700
C10—C11	1.387 (8)	C21—H21B	0.9700
C10—H10	0.9300	C22—C23	1.514 (8)
C11—C12	1.383 (9)	C22—H22A	0.9700
C11—H11	0.9300	C22—H22B	0.9700
C12—C13	1.389 (7)	C23—C24	1.498 (8)
C12—H12	0.9300	C23—H23B	0.9700
C13—H13	0.9300	C23—H23A	0.9700
C14—C19	1.507 (7)	C24—C25	1.511 (8)
C14—C15	1.513 (7)	C24—H24A	0.9700
C14—H14	0.9800	C24—H24B	0.9700
C15—C16	1.533 (8)	C25—H25A	0.9700
C15—H15A	0.9700	C25—H25B	0.9700
C15—H15B	0.9700
O2—P1—N6	117.2 (2)	C16—C17—C18	111.1 (5)
O2—P1—N5	115.7 (2)	C16—C17—H17B	109.4
N6—P1—N5	102.73 (19)	C18—C17—H17B	109.4
O2—P1—N4	103.77 (18)	C16—C17—H17A	109.4
N6—P1—N4	107.5 (2)	C18—C17—H17A	109.4
N5—P1—N4	109.79 (19)	H17B—C17—H17A	108.0
C7—N4—P1	123.0 (3)	C17—C18—C19	111.6 (5)
C7—N4—H4	113 (2)	C17—C18—H18A	109.3
P1—N4—H4	124 (2)	C19—C18—H18A	109.3
C14—N5—P1	125.4 (3)	C17—C18—H18B	109.3
C14—N5—H5	120 (4)	C19—C18—H18B	109.3
P1—N5—H5	109 (4)	H18A—C18—H18B	108.0
C20—N6—P1	125.2 (3)	C14—C19—C18	112.8 (5)
C20—N6—H6	113 (4)	C14—C19—H19A	109.0
P1—N6—H6	112 (4)	C18—C19—H19A	109.0
O3—C7—N4	122.2 (4)	C14—C19—H19B	109.0
O3—C7—C8	120.2 (4)	C18—C19—H19B	109.0
N4—C7—C8	117.6 (3)	H19A—C19—H19B	107.8
C9—C8—C13	118.6 (4)	N6—C20—C21	112.4 (4)
C9—C8—C7	123.4 (4)	N6—C20—C25	110.6 (4)
C13—C8—C7	117.9 (4)	C21—C20—C25	111.4 (4)
C10—C9—C8	121.6 (5)	N6—C20—H20	107.4
C10—C9—H9	119.2	C21—C20—H20	107.4
C8—C9—H9	119.2	C25—C20—H20	107.4
C9—C10—C11	119.7 (5)	C20—C21—C22	113.7 (5)
C9—C10—H10	120.1	C20—C21—H21A	108.8
C11—C10—H10	120.1	C22—C21—H21A	108.8
C12—C11—C10	120.2 (5)	C20—C21—H21B	108.8
C12—C11—H11	119.9	C22—C21—H21B	108.8
C10—C11—H11	119.9	H21A—C21—H21B	107.7
C11—C12—C13	119.6 (5)	C23—C22—C21	111.5 (5)
C11—C12—H12	120.2	C23—C22—H22A	109.3
C13—C12—H12	120.2	C21—C22—H22A	109.3
C12—C13—C8	120.3 (5)	C23—C22—H22B	109.3
C12—C13—H13	119.9	C21—C22—H22B	109.3
C8—C13—H13	119.9	H22A—C22—H22B	108.0
N5—C14—C19	113.5 (4)	C24—C23—C22	110.6 (5)
N5—C14—C15	108.8 (4)	C24—C23—H23B	109.5
C19—C14—C15	110.2 (4)	C22—C23—H23B	109.5
N5—C14—H14	108.1	C24—C23—H23A	109.5
C19—C14—H14	108.1	C22—C23—H23A	109.5
C15—C14—H14	108.1	H23B—C23—H23A	108.1
C14—C15—C16	112.7 (5)	C23—C24—C25	112.7 (5)
C14—C15—H15A	109.1	C23—C24—H24A	109.1
C16—C15—H15A	109.1	C25—C24—H24A	109.1
C14—C15—H15B	109.1	C23—C24—H24B	109.1
C16—C15—H15B	109.1	C25—C24—H24B	109.1
H15A—C15—H15B	107.8	H24A—C24—H24B	107.8
C17—C16—C15	111.6 (5)	C24—C25—C20	113.2 (5)
C17—C16—H16A	109.3	C24—C25—H25A	108.9
C15—C16—H16A	109.3	C20—C25—H25A	108.9
C17—C16—H16B	109.3	C24—C25—H25B	108.9
C15—C16—H16B	109.3	C20—C25—H25B	108.9
H16A—C16—H16B	108.0	H25A—C25—H25B	107.8
O2—P1—N4—C7	−174.9 (4)	C7—C8—C13—C12	175.4 (4)
N6—P1—N4—C7	60.3 (4)	P1—N5—C14—C19	74.0 (5)
N5—P1—N4—C7	−50.7 (4)	P1—N5—C14—C15	−162.9 (4)
O2—P1—N5—C14	37.2 (4)	N5—C14—C15—C16	−177.7 (5)
N6—P1—N5—C14	166.0 (4)	C19—C14—C15—C16	−52.6 (7)
N4—P1—N5—C14	−79.8 (4)	C14—C15—C16—C17	54.8 (8)
O2—P1—N6—C20	−61.0 (4)	C15—C16—C17—C18	−55.0 (8)
N5—P1—N6—C20	171.1 (4)	C16—C17—C18—C19	55.1 (8)
N4—P1—N6—C20	55.2 (4)	N5—C14—C19—C18	175.1 (5)
P1—N4—C7—O3	−7.5 (6)	C15—C14—C19—C18	52.8 (7)
P1—N4—C7—C8	170.5 (3)	C17—C18—C19—C14	−54.7 (8)
O3—C7—C8—C9	147.1 (4)	P1—N6—C20—C21	−124.3 (4)
N4—C7—C8—C9	−31.0 (6)	P1—N6—C20—C25	110.5 (4)
O3—C7—C8—C13	−28.7 (6)	N6—C20—C21—C22	−174.9 (5)
N4—C7—C8—C13	153.3 (4)	C25—C20—C21—C22	−50.1 (7)
C13—C8—C9—C10	1.2 (7)	C20—C21—C22—C23	53.6 (7)
C7—C8—C9—C10	−174.5 (5)	C21—C22—C23—C24	−54.7 (7)
C8—C9—C10—C11	−1.2 (8)	C22—C23—C24—C25	55.0 (7)
C9—C10—C11—C12	0.5 (8)	C23—C24—C25—C20	−52.9 (7)
C10—C11—C12—C13	0.1 (8)	N6—C20—C25—C24	175.3 (5)
C11—C12—C13—C8	−0.1 (8)	C21—C20—C25—C24	49.5 (7)
C9—C8—C13—C12	−0.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O3i	0.90 (4)	2.16 (4)	2.988 (4)	154 (3)
N5—H5···O2ii	0.77 (5)	2.30 (6)	3.019 (5)	156 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O3i	0.90 (4)	2.16 (4)	2.988 (4)	154 (3)
N5—H5⋯O2ii	0.77 (5)	2.30 (6)	3.019 (5)	156 (6)

Symmetry codes: (i) ; (ii) .