supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers Open access

ld2010 scheme

Acta Cryst. (2011). E67, o1360    [ doi:10.1107/S1600536811016679 ]

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

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

Abstract top

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.

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.

Refinement top

At the end of the refinement the highest peak in the electron density was 0.460 e Å -3, while the deepest hole was -0.180 e Å -3.

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
[Figure 1] Fig. 1. An ORTEP-style plot of title compound with labeling. Ellipsoids are given at the 50% probability level.
[Figure 2] 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
C19H30N3O2PF(000) = 784
Mr = 363.43Dx = 1.247 Mg m−3
Monoclinic, CcCu Kα radiation, λ = 1.54180 Å
Hall symbol: C -2ycCell parameters from 1733 reflections
a = 20.9904 (17) Åθ = 4.2–70.2°
b = 5.1503 (2) ŵ = 1.39 mm−1
c = 21.1125 (18) ÅT = 293 K
β = 121.955 (11)°Prismatic, colorless
V = 1936.5 (2) Å30.28 × 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 Source2294 reflections with I > 2σ(I)
graphiteRint = 0.064
Detector resolution: 10.2673 pixels mm-1θmax = 70.3°, θmin = 4.8°
ω scansh = −24→24
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		k = 0→6
Tmin = 0.978, Tmax = 1.000l = −25→25
2758 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H 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 reflectionsΔρmax = 0.46 e Å−3
239 parametersΔρmin = −0.18 e Å−3
2 restraintsAbsolute structure: Flack (1983), 908 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.11 (4)
Crystal data top
C19H30N3O2PV = 1936.5 (2) Å3
Mr = 363.43Z = 4
Monoclinic, CcCu Kα radiation
a = 20.9904 (17) ŵ = 1.39 mm−1
b = 5.1503 (2) ÅT = 293 K
c = 21.1125 (18) Å0.28 × 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)
Tmin = 0.978, Tmax = 1.000Rint = 0.064
2758 measured reflectionsθmax = 70.3°
Refinement top
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122Δρmax = 0.46 e Å−3
S = 1.05Δρmin = −0.18 e Å−3
2758 reflectionsAbsolute structure: Flack (1983), 908 Friedel pairs
239 parametersFlack 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
xyzUiso*/Ueq
P10.00072 (6)0.2629 (2)0.30701 (6)0.0403 (2)
O2−0.02706 (18)0.5292 (5)0.30029 (19)0.0504 (8)
O30.11281 (18)−0.1251 (6)0.3206 (2)0.0578 (9)
N40.0865 (2)0.3029 (6)0.3150 (2)0.0435 (8)
N5−0.0520 (2)0.0724 (7)0.2376 (2)0.0438 (9)
N60.0150 (2)0.0959 (8)0.3781 (2)0.0458 (9)
C70.1289 (2)0.1008 (8)0.3169 (2)0.0398 (9)
C80.1958 (2)0.1615 (7)0.3117 (2)0.0401 (9)
C90.1990 (3)0.3714 (9)0.2727 (3)0.0490 (11)
H90.15980.49050.25180.059*
C100.2585 (3)0.4083 (11)0.2640 (3)0.0616 (13)
H100.25900.54920.23670.074*
C110.3180 (3)0.2347 (12)0.2961 (3)0.0677 (14)
H110.35870.26000.29070.081*
C120.3169 (3)0.0239 (12)0.3362 (3)0.0722 (16)
H120.3569−0.09230.35770.087*
C130.2559 (3)−0.0130 (10)0.3440 (3)0.0533 (12)
H130.2549−0.15460.37080.064*
C14−0.0945 (2)0.1484 (9)0.1595 (2)0.0451 (10)
H14−0.12030.31200.15540.054*
C15−0.1535 (3)−0.0560 (13)0.1154 (3)0.0727 (17)
H15A−0.1872−0.06650.13360.087*
H15B−0.1292−0.22340.12350.087*
C16−0.1994 (3)0.0014 (16)0.0314 (3)0.0846 (19)
H16A−0.2337−0.14130.00550.102*
H16B−0.22900.15710.02250.102*
C17−0.1502 (3)0.0381 (11)0.0011 (3)0.0638 (13)
H17B−0.18060.0862−0.05110.077*
H17A−0.1251−0.12410.00450.077*
C18−0.0922 (4)0.2463 (12)0.0436 (4)0.0774 (17)
H18A−0.11720.41250.03520.093*
H18B−0.05890.25790.02500.093*
C19−0.0464 (3)0.1896 (13)0.1269 (3)0.0683 (16)
H19A−0.01620.03560.13560.082*
H19B−0.01240.33350.15250.082*
C200.0677 (2)0.1637 (8)0.4557 (2)0.0426 (9)
H200.09620.31510.45620.051*
C210.1229 (3)−0.0486 (12)0.4978 (3)0.0685 (15)
H21A0.1533−0.07580.47630.082*
H21B0.0956−0.20810.49160.082*
C220.1746 (3)0.0067 (15)0.5810 (3)0.0805 (19)
H22A0.2054−0.14480.60550.097*
H22B0.20770.14980.58780.097*
C230.1303 (3)0.0742 (10)0.6167 (3)0.0650 (14)
H23B0.1019−0.07620.61550.078*
H23A0.16460.12180.66850.078*
C240.0777 (4)0.2951 (13)0.5762 (3)0.0771 (18)
H24A0.10680.45050.58290.093*
H24B0.04770.32710.59790.093*
C250.0261 (3)0.2433 (12)0.4937 (3)0.0654 (15)
H25A−0.00290.39870.46970.078*
H25B−0.00880.10660.48680.078*
H40.1046 (19)0.457 (7)0.3124 (19)0.015 (8)*
H60.014 (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
U11U22U33U12U13U23
P10.0447 (5)0.0336 (4)0.0472 (5)0.0016 (5)0.0276 (4)0.0017 (5)
O20.0546 (17)0.0351 (15)0.071 (2)0.0019 (13)0.0401 (17)0.0037 (14)
O30.061 (2)0.0334 (17)0.089 (3)0.0009 (14)0.047 (2)0.0017 (15)
N40.0453 (19)0.0326 (18)0.060 (2)0.0006 (15)0.0333 (18)−0.0008 (15)
N50.048 (2)0.035 (2)0.047 (2)0.0003 (16)0.0244 (18)0.0047 (16)
N60.054 (2)0.044 (2)0.046 (2)−0.0048 (18)0.0301 (19)−0.0002 (17)
C70.0389 (19)0.036 (2)0.045 (2)0.0004 (17)0.0228 (18)0.0000 (17)
C80.041 (2)0.0367 (19)0.042 (2)0.0018 (17)0.0213 (18)−0.0041 (17)
C90.052 (3)0.045 (2)0.059 (3)0.002 (2)0.035 (2)−0.003 (2)
C100.068 (3)0.062 (3)0.076 (3)−0.003 (3)0.053 (3)−0.003 (3)
C110.055 (3)0.074 (4)0.091 (4)−0.011 (3)0.050 (3)−0.019 (3)
C120.037 (3)0.076 (4)0.091 (4)0.011 (2)0.026 (3)−0.016 (3)
C130.046 (2)0.049 (3)0.057 (3)0.006 (2)0.022 (2)−0.002 (2)
C140.048 (2)0.042 (2)0.045 (3)0.0027 (19)0.024 (2)0.0002 (19)
C150.064 (3)0.103 (5)0.050 (3)−0.034 (3)0.030 (3)−0.006 (3)
C160.059 (3)0.116 (5)0.064 (4)−0.015 (3)0.023 (3)−0.008 (4)
C170.079 (3)0.057 (3)0.052 (3)0.003 (3)0.032 (3)0.004 (2)
C180.107 (4)0.070 (4)0.067 (4)−0.019 (4)0.054 (4)−0.003 (3)
C190.060 (3)0.091 (4)0.056 (3)−0.024 (3)0.033 (3)0.001 (3)
C200.045 (2)0.041 (2)0.045 (2)0.0004 (18)0.025 (2)0.0032 (18)
C210.074 (3)0.077 (4)0.057 (3)0.027 (3)0.037 (3)0.010 (3)
C220.065 (3)0.114 (5)0.051 (4)0.028 (4)0.022 (3)0.018 (3)
C230.083 (4)0.055 (3)0.053 (3)−0.001 (3)0.034 (3)0.004 (2)
C240.102 (5)0.075 (4)0.056 (3)0.017 (4)0.043 (3)0.000 (3)
C250.071 (3)0.078 (4)0.057 (3)0.023 (3)0.040 (3)0.006 (3)
Geometric parameters (Å, °) top
P1—O21.468 (3)C16—C171.487 (8)
P1—N61.615 (4)C16—H16A0.9700
P1—N51.618 (4)C16—H16B0.9700
P1—N41.730 (4)C17—C181.509 (8)
O3—C71.225 (5)C17—H17B0.9700
N4—C71.356 (5)C17—H17A0.9700
N4—H40.90 (4)C18—C191.521 (9)
N5—C141.454 (6)C18—H18A0.9700
N5—H50.77 (5)C18—H18B0.9700
N6—C201.453 (6)C19—H19A0.9700
N6—H60.78 (4)C19—H19B0.9700
C7—C81.499 (6)C20—C211.496 (7)
C8—C91.382 (6)C20—C251.521 (6)
C8—C131.397 (6)C20—H200.9800
C9—C101.366 (7)C21—C221.525 (8)
C9—H90.9300C21—H21A0.9700
C10—C111.387 (8)C21—H21B0.9700
C10—H100.9300C22—C231.514 (8)
C11—C121.383 (9)C22—H22A0.9700
C11—H110.9300C22—H22B0.9700
C12—C131.389 (7)C23—C241.498 (8)
C12—H120.9300C23—H23B0.9700
C13—H130.9300C23—H23A0.9700
C14—C191.507 (7)C24—C251.511 (8)
C14—C151.513 (7)C24—H24A0.9700
C14—H140.9800C24—H24B0.9700
C15—C161.533 (8)C25—H25A0.9700
C15—H15A0.9700C25—H25B0.9700
C15—H15B0.9700
O2—P1—N6117.2 (2)C16—C17—C18111.1 (5)
O2—P1—N5115.7 (2)C16—C17—H17B109.4
N6—P1—N5102.73 (19)C18—C17—H17B109.4
O2—P1—N4103.77 (18)C16—C17—H17A109.4
N6—P1—N4107.5 (2)C18—C17—H17A109.4
N5—P1—N4109.79 (19)H17B—C17—H17A108.0
C7—N4—P1123.0 (3)C17—C18—C19111.6 (5)
C7—N4—H4113 (2)C17—C18—H18A109.3
P1—N4—H4124 (2)C19—C18—H18A109.3
C14—N5—P1125.4 (3)C17—C18—H18B109.3
C14—N5—H5120 (4)C19—C18—H18B109.3
P1—N5—H5109 (4)H18A—C18—H18B108.0
C20—N6—P1125.2 (3)C14—C19—C18112.8 (5)
C20—N6—H6113 (4)C14—C19—H19A109.0
P1—N6—H6112 (4)C18—C19—H19A109.0
O3—C7—N4122.2 (4)C14—C19—H19B109.0
O3—C7—C8120.2 (4)C18—C19—H19B109.0
N4—C7—C8117.6 (3)H19A—C19—H19B107.8
C9—C8—C13118.6 (4)N6—C20—C21112.4 (4)
C9—C8—C7123.4 (4)N6—C20—C25110.6 (4)
C13—C8—C7117.9 (4)C21—C20—C25111.4 (4)
C10—C9—C8121.6 (5)N6—C20—H20107.4
C10—C9—H9119.2C21—C20—H20107.4
C8—C9—H9119.2C25—C20—H20107.4
C9—C10—C11119.7 (5)C20—C21—C22113.7 (5)
C9—C10—H10120.1C20—C21—H21A108.8
C11—C10—H10120.1C22—C21—H21A108.8
C12—C11—C10120.2 (5)C20—C21—H21B108.8
C12—C11—H11119.9C22—C21—H21B108.8
C10—C11—H11119.9H21A—C21—H21B107.7
C11—C12—C13119.6 (5)C23—C22—C21111.5 (5)
C11—C12—H12120.2C23—C22—H22A109.3
C13—C12—H12120.2C21—C22—H22A109.3
C12—C13—C8120.3 (5)C23—C22—H22B109.3
C12—C13—H13119.9C21—C22—H22B109.3
C8—C13—H13119.9H22A—C22—H22B108.0
N5—C14—C19113.5 (4)C24—C23—C22110.6 (5)
N5—C14—C15108.8 (4)C24—C23—H23B109.5
C19—C14—C15110.2 (4)C22—C23—H23B109.5
N5—C14—H14108.1C24—C23—H23A109.5
C19—C14—H14108.1C22—C23—H23A109.5
C15—C14—H14108.1H23B—C23—H23A108.1
C14—C15—C16112.7 (5)C23—C24—C25112.7 (5)
C14—C15—H15A109.1C23—C24—H24A109.1
C16—C15—H15A109.1C25—C24—H24A109.1
C14—C15—H15B109.1C23—C24—H24B109.1
C16—C15—H15B109.1C25—C24—H24B109.1
H15A—C15—H15B107.8H24A—C24—H24B107.8
C17—C16—C15111.6 (5)C24—C25—C20113.2 (5)
C17—C16—H16A109.3C24—C25—H25A108.9
C15—C16—H16A109.3C20—C25—H25A108.9
C17—C16—H16B109.3C24—C25—H25B108.9
C15—C16—H16B109.3C20—C25—H25B108.9
H16A—C16—H16B108.0H25A—C25—H25B107.8
O2—P1—N4—C7−174.9 (4)C7—C8—C13—C12175.4 (4)
N6—P1—N4—C760.3 (4)P1—N5—C14—C1974.0 (5)
N5—P1—N4—C7−50.7 (4)P1—N5—C14—C15−162.9 (4)
O2—P1—N5—C1437.2 (4)N5—C14—C15—C16−177.7 (5)
N6—P1—N5—C14166.0 (4)C19—C14—C15—C16−52.6 (7)
N4—P1—N5—C14−79.8 (4)C14—C15—C16—C1754.8 (8)
O2—P1—N6—C20−61.0 (4)C15—C16—C17—C18−55.0 (8)
N5—P1—N6—C20171.1 (4)C16—C17—C18—C1955.1 (8)
N4—P1—N6—C2055.2 (4)N5—C14—C19—C18175.1 (5)
P1—N4—C7—O3−7.5 (6)C15—C14—C19—C1852.8 (7)
P1—N4—C7—C8170.5 (3)C17—C18—C19—C14−54.7 (8)
O3—C7—C8—C9147.1 (4)P1—N6—C20—C21−124.3 (4)
N4—C7—C8—C9−31.0 (6)P1—N6—C20—C25110.5 (4)
O3—C7—C8—C13−28.7 (6)N6—C20—C21—C22−174.9 (5)
N4—C7—C8—C13153.3 (4)C25—C20—C21—C22−50.1 (7)
C13—C8—C9—C101.2 (7)C20—C21—C22—C2353.6 (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—C2555.0 (7)
C9—C10—C11—C120.5 (8)C23—C24—C25—C20−52.9 (7)
C10—C11—C12—C130.1 (8)N6—C20—C25—C24175.3 (5)
C11—C12—C13—C8−0.1 (8)C21—C20—C25—C2449.5 (7)
C9—C8—C13—C12−0.6 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O3i0.90 (4)2.16 (4)2.988 (4)154 (3)
N5—H5···O2ii0.77 (5)2.30 (6)3.019 (5)156 (6)
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O3i0.90 (4)2.16 (4)2.988 (4)154 (3)
N5—H5···O2ii0.77 (5)2.30 (6)3.019 (5)156 (6)
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.
Acknowledgements top

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
References top

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Gholivand, K., Mojahed, F., Madani Alizadehgan, A. & Bijanzadeh, H. R. (2006). Z. Anorg. Allg. Chem. 632, 1570–1577.

Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.

Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.

Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790.

Rudd, M. D., Lindeman, S. V. & Husebye, S. (1996). Acta Chem. Scand. 50, 759–774.

Sabbaghi, F., Pourayoubi, M., Toghraee, M. & Divjakovic, V. (2010). Acta Cryst. E66, o344.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.