N-Benzoyl-N′,N′′-dicyclo­hexyl­phospho­ric triamide

Pourayoubi, M.; Rostami Chaijan, M.; Torre-Fernández, L.; García-Granda, S.

doi:10.1107/S1600536811016679

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1360

doi:10.1107/S1600536811016679

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N-Benzoyl-N′,N′′-dicyclohexylphosphoric triamide

Mehrdad Pourayoubi,^a Mahnaz Rostami Chaijan,^a Laura Torre-Fernández ^b and Santiago García-Granda ^b ^*

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDepartamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo–CINN, C/ Julián Clavería, 8, 33006 Oviedo, Asturias, Spain
^*Correspondence e-mail: sgg@uniovi.es

(Received 14 April 2011; accepted 3 May 2011; online 7 May 2011)

In the title compound, C₁₉H₃₀N₃O₂P, the central P atom has a distorted tetrahedral configuration. The N atoms in both cyclohexylamide moieties exhibit a slight deviation [0.32 (7) and 0.44 (6) Å] from planarity, while the benzoylamide N atom is planar [0.11 (3) Å]. In the crystal, molecules are linked via N—H⋯O(P) and N—H⋯O(C) hydrogen bonds, forming R₂²(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_r = 363.43
Monoclinic, C c
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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.122
S = 1.05
2758 reflections
239 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 908 Friedel pairs
Flack parameter: 0.11 (4)

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) x, y+1, z; (ii) x, y-1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

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

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

checkCIF report

Comment top

The synthesis of the title compound, C₆H₅C(O)NHP(O)[NHC₆H₁₁]₂, was previously published by Gholivand et al. (2006). Here, we report its crystal structure (Fig. 1).

The P═O, C═O and P—N bond lengths match those found for other compounds with the [(N)(N)P(O)NHC(O)] skeleton (Sabbaghi et al., 2010). The nitrogen atoms show sp² character and the environment of N atom in C(O)NHP(O) moiety is practically planar. The tetrahedral configuration of phosphorus atom is significantly distorted (Fig. 1) as it has been noted for other phosphoric triamides and their chalco-derivatives (Rudd et al., 1996): the bond angles at the P atom vary in the range from 102.7 (2)° to 117.2 (2)°, while the P–N bond distances range form 1.615 (4) to 1.730 (4) Å. Cyclohexyl groups are in a chair conformation with the adjacent NH groups oriented equatorially.

The NH unit of the C(O)NHP(O) moiety adopts a syn orientation with respect to the phosphoryl group; moreover, the NH units of two C₆H₁₁NH moieties are in a syn orientation with respect to each other.

In the crystal structure, the molecules are linked via N—H···O═P and N—H···O═C hydrogen bonds, in which carbonyl oxygen interacts with benzamide N—H and P(O) group binds to a cyclohexylamido moiety. This way, R₂²(10) rings are built (Etter et al., 1990; Bernstein et al., 1995), that are further connected in linear arrangements along y axis (Table 1, Fig. 2).

Related literature top

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 top

C₆H₅C(O)NHP(O)[NHC₆H₁₁]₂ was prepared according to the procedure reported by Gholivand et al. (2006). Single crystals of title compound were obtained from CH₃OH after slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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).

Figures top

	Fig. 1. An ORTEP-style plot of title compound with labeling. Ellipsoids are given at the 50% probability level.
	Fig. 2. Partial packing view showing the formation of the chain through N—H···O hydrogen bonds (along the b axis) which are shown as dotted lines. H atoms not involved in the hydrogen bondings are omitted.

N-Benzoyl-N',N''-dicyclohexylphosphoric triamide top

Crystal data top

C₁₉H₃₀N₃O₂P	F(000) = 784
M_r = 363.43	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0489P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2758 reflections	Δρ_max = 0.46 e Å⁻³
239 parameters	Δρ_min = −0.18 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 908 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.11 (4)

Crystal data top

C₁₉H₃₀N₃O₂P	V = 1936.5 (2) Å³
M_r = 363.43	Z = 4
Monoclinic, Cc	Cu Kα radiation
a = 20.9904 (17) Å	µ = 1.39 mm⁻¹
b = 5.1503 (2) Å	T = 293 K
c = 21.1125 (18) Å	0.28 × 0.05 × 0.01 mm
β = 121.955 (11)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2758 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2294 reflections with I > 2σ(I)
T_min = 0.978, T_max = 1.000	R_int = 0.064
2758 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.122	Δρ_max = 0.46 e Å⁻³
S = 1.05	Δρ_min = −0.18 e Å⁻³
2758 reflections	Absolute structure: Flack (1983), 908 Friedel pairs
239 parameters	Absolute structure parameter: 0.11 (4)
2 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₃₀N₃O₂P
M_r	363.43
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	20.9904 (17), 5.1503 (2), 21.1125 (18)
β (°)	121.955 (11)
V (Å³)	1936.5 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.39
Crystal size (mm)	0.28 × 0.05 × 0.01

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.978, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	2758, 2758, 2294
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.122, 1.05
No. of reflections	2758
No. of parameters	239
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.18
Absolute structure	Flack (1983), 908 Friedel pairs
Absolute structure parameter	0.11 (4)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SUPERFLIP (Palatinus & Chapuis, 2007), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) x, y−1, z.

Acknowledgements

Financial support from the Spanish Ministerio de Ciencia e Innovación (MAT2006–01997, MAT2010–15094 and `Factoría de Cristalización' Consolider Ingenio 2010) and FEDER funding is acknowledged.

References

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