N,N-Bis(diphenyl­phosphan­yl)cyclo­­penta­namine

Engelbrecht, I.; Visser, H.G.; Roodt, A.

doi:10.1107/S1600536810048907

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3322-o3323

https://doi.org/10.1107/S1600536810048907

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N,N-Bis(diphenylphosphanyl)cyclopentanamine

Ilana Engelbrecht,^a ^* Hendrik G. Visser ^a and Andreas Roodt ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
^*Correspondence e-mail: EngelbrechtI@ufs.ac.za

(Received 21 October 2010; accepted 23 November 2010; online 27 November 2010)

The coordination around the N atom in the title compound, C₂₉H₂₉NP₂, shows an almost planar geometry, defined by the attached P and C atoms, in order to accomodate the steric bulk of the phenyl rings. The distortion of the trigonal–pyramidal geometry of the N atom is illustrated by the bond angles ranging between 115.22 (12) and 121.76 (9)°. The P atoms present a pyramidal environment with bond angles ranging from 100.62 (9) to 104.71 (8)°. One of the C atoms in the cyclopentyl ring displays a 0.822 (4):0.178 (4) positional disorder. Within the crystal structure, intramolecular C—H⋯P hydrogen bonds together with inter- and intramolecular C—H⋯π interactions link the molecules into a supramolecular two-dimensional network.

Related literature

For similar structures, see: Keat et al. (1981 ); Cotton et al. (1996 ); Fei et al. (2003 ); Cloete et al. (2008 , 2009 , 2010 ); Engelbrecht et al. (2010 ).

Experimental

Crystal data

C₂₉H₂₉NP₂
M_r = 453.47
Triclinic, $[P \overline 1]$
a = 8.803 (5) Å
b = 11.166 (4) Å
c = 12.685 (5) Å
α = 97.144 (4)°
β = 101.261 (5)°
γ = 99.707 (5)°
V = 1189.3 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.2 mm⁻¹
T = 100 K
0.19 × 0.13 × 0.08 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.963, T_max = 0.983
12794 measured reflections
5817 independent reflections
4333 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.106
S = 1.06
5817 reflections
293 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯P2	0.99	2.82	3.269 (2)	108
C5A—H5A1⋯P2	0.99	2.82	3.202 (3)	104
C12—H12⋯Cg1	0.95	2.72	3.667 (2)	174
C3A—H3A2⋯Cg1ⁱ	0.99	2.89	3.811 (2)	155
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810048907/bg2375sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048907/bg2375Isup2.hkl

checkCIF report

Comment top

Diphosphinoamine (PNP) ligands form part of ongoing research in ethylene tetramerization catalyst systems. In the title compound, C₂₉H₂₉NP₂, all bond distances and angles fall within the range for similar complexes (Keat et al., 1981; Cotton et al., 1996; Fei et al., 2003; Cloete et al., 2008, 2009, 2010; Engelbrecht et al., 2010) The N(P₂C) group is almost planar, with the central N displaced by -0.120 (2)Å from the plane defined by the remaining three atoms (P1, P2, C1). The distorted trigonal-pyramidal geometry around the N atom is further illustrated by the bond angles ranging between 115.22 (12)° and 121.76 (9)°. The diphenylphosphino groups are staggered relative to the PNP backbone and form with each other dihedral angles of 68.84 (4)° (C11 and C21, bonded to P1) and 68.43 (4)° (C31 and C41, bonded to P2). The geometry around the phosphorous atoms is that of a distorted triangular pyramid, with C—P—C angles in the range 100.62 (9)° - 101.65 (8)° and N—P—C angles with a 101.65 (8)° - 104.71 (8)° span. One carbon atom in the cyclopentyl ring is disordered over two positions in a 0.822 (4):0.178 (4) ratio (Fig 1). There are some C—H···P intramolecular H-bonds as well as a few C—H···π interactions which contribute to the supramolecular aggregation (Table 1, Figure 2).

Related literature top

For similar structures, see: Keat et al. (1981); Cotton et al. (1996); Fei et al. (2003); Cloete et al. (2008, 2009, 2010); Engelbrecht et al. (2010).

Experimental top

Cyclopentylamine (0.010 mol, 1.00 ml) was dissolved in dichloromethane (30 ml) after which the solution was placed on an ice bath. Triethylamine (0.030 mol, 4.21 ml) was added to the solution while stirring. Chlorodiphenylphosphine (0.020 mol, 3.70 ml) was slowly added to the reaction mixture. The ice bath was removed after 1 h and the reaction mixture was allowed to stir at room temperature for a further 12 h. The dichloromethane was removed under reduced pressure. A mixture of hexane (20 ml) and toluene (2 ml) was added to the remaining white powder and was passed through a column containing neutral activated alumina (35 g). The solvent of the eluent was removed under reduced pressure and the white precipitate was collected. Single colourless crystals suitable for X-ray crystallography were obtained from recrystallization from methanol. (yield: 1.010 g, 22%)

Structure description top

For similar structures, see: Keat et al. (1981); Cotton et al. (1996); Fei et al. (2003); Cloete et al. (2008, 2009, 2010); Engelbrecht et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines denote the minor disordered atoms. Only applicable hydrogen atoms with relevance to C—H···P intramolecular hydrogen bonds are indicated.
	Fig. 2. The crystal packing of the title compound showing the two-dimensional network. C—H···π interactions are shown as dashed lines.

N,N-Bis(diphenylphosphanyl)cyclopentanamine top

Crystal data top

C₂₉H₂₉NP₂	Z = 2
M_r = 453.47	F(000) = 480
Triclinic, P1	D_x = 1.266 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.803 (5) Å	Cell parameters from 2872 reflections
b = 11.166 (4) Å	θ = 2.7–28.0°
c = 12.685 (5) Å	µ = 0.2 mm⁻¹
α = 97.144 (4)°	T = 100 K
β = 101.261 (5)°	Cuboid, white
γ = 99.707 (5)°	0.19 × 0.13 × 0.08 mm
V = 1189.3 (10) Å³

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	5817 independent reflections
Radiation source: fine-focus sealed tube	4333 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω and φ scans	θ_max = 28.3°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.963, T_max = 0.983	k = −14→14
12794 measured reflections	l = −16→16

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0343P)² + 0.5079P] where P = (F_o² + 2F_c²)/3
5817 reflections	(Δ/σ)_max = 0.015
293 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₉H₂₉NP₂	γ = 99.707 (5)°
M_r = 453.47	V = 1189.3 (10) Å³
Triclinic, P1	Z = 2
a = 8.803 (5) Å	Mo Kα radiation
b = 11.166 (4) Å	µ = 0.2 mm⁻¹
c = 12.685 (5) Å	T = 100 K
α = 97.144 (4)°	0.19 × 0.13 × 0.08 mm
β = 101.261 (5)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	5817 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4333 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.983	R_int = 0.035
12794 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.06	Δρ_max = 0.34 e Å⁻³
5817 reflections	Δρ_min = −0.33 e Å⁻³
293 parameters

Special details top

Experimental. The intensity data were collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 60 s/frame. A total of 1148 frames were collected with a frame width of 0.5° covering up to θ = 28.27° with 98.7% completeness accomplished. Spectroscopy data: ¹H NMR (300 MHz, CD₂Cl₂): δ = 1.3 to 1.9 (m, 8H, 4 x CH₂), 3.8 (m, 1H, CH), 7.3 to 7.4 (m, 20H, Ar); ³¹P NMR (121 MHz, CD₂Cl₂): δ = 50.6 (s).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
C1	0.91678 (19)	0.34252 (17)	0.75151 (15)	0.0160 (4)
H1	0.9698	0.278	0.7211	0.019*
C2	0.9126 (2)	0.44037 (18)	0.67528 (16)	0.0198 (4)
H2A	0.9168	0.4043	0.6008	0.024*
H2B	0.8154	0.4746	0.6716	0.024*
C3A	1.0595 (2)	0.5401 (2)	0.72654 (18)	0.0283 (5)	0.822 (4)
H3A1	1.0467	0.6203	0.7042	0.034*	0.822 (4)
H3A2	1.1549	0.5173	0.706	0.034*	0.822 (4)
C4A	1.0695 (3)	0.5448 (2)	0.8501 (2)	0.0252 (6)	0.822 (4)
H4A1	1.1775	0.5823	0.8926	0.03*	0.822 (4)
H4A2	0.9939	0.5922	0.8748	0.03*	0.822 (4)
C5A	1.0262 (2)	0.41072 (18)	0.86124 (16)	0.0222 (4)	0.822 (4)
H5A1	0.9707	0.4024	0.9215	0.027*	0.822 (4)
H5A2	1.1226	0.3755	0.8771	0.027*	0.822 (4)
C3B	1.0595 (2)	0.5401 (2)	0.72654 (18)	0.0283 (5)	0.178 (4)
H3B1	1.1228	0.5556	0.6714	0.034*	0.178 (4)
H3B2	1.0268	0.6177	0.7509	0.034*	0.178 (4)
C4B	1.1460 (13)	0.5064 (11)	0.8099 (10)	0.0252 (6)	0.178 (4)
H4B1	1.1998	0.5793	0.8655	0.03*	0.178 (4)
H4B2	1.2274	0.4649	0.7861	0.03*	0.178 (4)
C5B	1.0262 (2)	0.41072 (18)	0.86124 (16)	0.0222 (4)	0.178 (4)
H5B1	1.0822	0.3549	0.9018	0.027*	0.178 (4)
H5B2	0.9686	0.4545	0.9082	0.027*	0.178 (4)
C11	0.7060 (2)	0.13812 (17)	0.55819 (15)	0.0155 (4)
C12	0.6196 (2)	0.20991 (19)	0.49657 (16)	0.0222 (4)
H12	0.5488	0.2514	0.5273	0.027*
C13	0.6355 (2)	0.22151 (19)	0.39194 (16)	0.0222 (4)
H13	0.5776	0.2722	0.3521	0.027*
C14	0.7355 (2)	0.15971 (18)	0.34479 (16)	0.0193 (4)
H14	0.7461	0.1676	0.2727	0.023*
C15	0.8197 (2)	0.08648 (19)	0.40339 (16)	0.0228 (4)
H15	0.8877	0.0431	0.3713	0.027*
C16	0.8051 (2)	0.07612 (18)	0.50916 (16)	0.0191 (4)
H16	0.8639	0.0258	0.5487	0.023*
C21	0.8152 (2)	0.03788 (17)	0.74897 (15)	0.0164 (4)
C22	0.7770 (2)	−0.08818 (18)	0.70735 (16)	0.0199 (4)
H22	0.688	−0.1188	0.6487	0.024*
C23	0.8659 (2)	−0.16896 (18)	0.74967 (16)	0.0218 (4)
H23	0.8371	−0.2543	0.7205	0.026*
C24	0.9970 (2)	−0.12568 (19)	0.83469 (16)	0.0227 (4)
H24	1.058	−0.1811	0.8642	0.027*
C25	1.0383 (2)	−0.00127 (19)	0.87619 (17)	0.0239 (4)
H25	1.1293	0.029	0.9334	0.029*
C26	0.9474 (2)	0.08001 (18)	0.83467 (16)	0.0206 (4)
H26	0.9757	0.165	0.865	0.025*
C31	0.4685 (2)	0.35868 (17)	0.71326 (15)	0.0157 (4)
C32	0.4624 (2)	0.45295 (19)	0.65030 (16)	0.0204 (4)
H32	0.5452	0.5236	0.6677	0.024*
C33	0.3364 (2)	0.4442 (2)	0.56256 (17)	0.0253 (5)
H33	0.3344	0.5081	0.5197	0.03*
C34	0.2143 (2)	0.3431 (2)	0.53752 (16)	0.0246 (5)
H34	0.1288	0.337	0.4771	0.03*
C35	0.2165 (2)	0.24971 (19)	0.60091 (16)	0.0227 (4)
H35	0.1317	0.1805	0.5843	0.027*
C36	0.3429 (2)	0.25774 (18)	0.68856 (16)	0.0191 (4)
H36	0.3436	0.1941	0.7318	0.023*
C41	0.5704 (2)	0.29021 (17)	0.91837 (15)	0.0163 (4)
C42	0.4502 (2)	0.33272 (19)	0.96094 (16)	0.0207 (4)
H42	0.4064	0.3973	0.9326	0.025*
C43	0.3941 (2)	0.2821 (2)	1.04375 (17)	0.0257 (5)
H43	0.312	0.3116	1.0713	0.031*
C44	0.4581 (2)	0.1883 (2)	1.08629 (16)	0.0246 (4)
H44	0.4195	0.1529	1.1427	0.03*
C45	0.5785 (2)	0.14650 (19)	1.04613 (16)	0.0220 (4)
H45	0.6231	0.0828	1.0756	0.026*
C46	0.6347 (2)	0.19717 (18)	0.96279 (15)	0.0184 (4)
H46	0.7175	0.168	0.9361	0.022*
N1	0.75799 (16)	0.27932 (14)	0.76314 (12)	0.0155 (3)
P1	0.67417 (5)	0.13242 (5)	0.69726 (4)	0.01549 (12)
P2	0.64933 (5)	0.37383 (5)	0.81951 (4)	0.01544 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0132 (8)	0.0182 (10)	0.0159 (10)	0.0018 (7)	0.0040 (7)	0.0010 (8)
C2	0.0180 (8)	0.0241 (11)	0.0195 (10)	0.0056 (8)	0.0058 (8)	0.0071 (8)
C3A	0.0296 (11)	0.0227 (12)	0.0311 (13)	−0.0010 (9)	0.0105 (9)	0.0010 (10)
C4A	0.0254 (12)	0.0214 (14)	0.0251 (14)	−0.0007 (10)	0.0044 (10)	−0.0016 (11)
C5A	0.0175 (9)	0.0259 (12)	0.0199 (11)	0.0022 (8)	0.0009 (8)	−0.0006 (9)
C3B	0.0296 (11)	0.0227 (12)	0.0311 (13)	−0.0010 (9)	0.0105 (9)	0.0010 (10)
C4B	0.0254 (12)	0.0214 (14)	0.0251 (14)	−0.0007 (10)	0.0044 (10)	−0.0016 (11)
C5B	0.0175 (9)	0.0259 (12)	0.0199 (11)	0.0022 (8)	0.0009 (8)	−0.0006 (9)
C11	0.0151 (8)	0.0143 (9)	0.0138 (9)	−0.0017 (7)	0.0014 (7)	−0.0009 (7)
C12	0.0241 (9)	0.0267 (12)	0.0176 (11)	0.0114 (8)	0.0041 (8)	0.0019 (9)
C13	0.0274 (10)	0.0220 (11)	0.0167 (10)	0.0080 (8)	0.0000 (8)	0.0045 (8)
C14	0.0207 (9)	0.0220 (11)	0.0127 (10)	−0.0017 (8)	0.0026 (7)	0.0034 (8)
C15	0.0233 (9)	0.0285 (12)	0.0206 (11)	0.0085 (9)	0.0095 (8)	0.0067 (9)
C16	0.0193 (9)	0.0230 (11)	0.0166 (10)	0.0066 (8)	0.0042 (8)	0.0058 (8)
C21	0.0194 (8)	0.0189 (10)	0.0141 (10)	0.0055 (8)	0.0078 (7)	0.0055 (8)
C22	0.0227 (9)	0.0192 (10)	0.0173 (10)	0.0018 (8)	0.0060 (8)	0.0022 (8)
C23	0.0304 (10)	0.0160 (10)	0.0224 (11)	0.0056 (8)	0.0124 (9)	0.0036 (8)
C24	0.0295 (10)	0.0242 (11)	0.0202 (11)	0.0129 (9)	0.0101 (9)	0.0082 (9)
C25	0.0279 (10)	0.0267 (12)	0.0170 (10)	0.0101 (9)	0.0011 (8)	0.0024 (9)
C26	0.0274 (10)	0.0179 (10)	0.0169 (10)	0.0068 (8)	0.0043 (8)	0.0017 (8)
C31	0.0157 (8)	0.0190 (10)	0.0141 (9)	0.0065 (7)	0.0051 (7)	0.0016 (8)
C32	0.0181 (9)	0.0226 (11)	0.0224 (11)	0.0051 (8)	0.0074 (8)	0.0049 (9)
C33	0.0265 (10)	0.0344 (13)	0.0210 (11)	0.0153 (9)	0.0079 (9)	0.0103 (9)
C34	0.0226 (9)	0.0375 (13)	0.0143 (10)	0.0151 (9)	0.0010 (8)	−0.0008 (9)
C35	0.0185 (9)	0.0248 (11)	0.0214 (11)	0.0041 (8)	0.0009 (8)	−0.0039 (9)
C36	0.0199 (9)	0.0191 (10)	0.0188 (10)	0.0049 (8)	0.0053 (8)	0.0017 (8)
C41	0.0150 (8)	0.0184 (10)	0.0131 (9)	0.0008 (7)	0.0018 (7)	−0.0005 (8)
C42	0.0193 (9)	0.0260 (11)	0.0183 (10)	0.0073 (8)	0.0053 (8)	0.0041 (9)
C43	0.0213 (9)	0.0368 (13)	0.0204 (11)	0.0066 (9)	0.0085 (8)	0.0026 (9)
C44	0.0259 (10)	0.0309 (12)	0.0150 (10)	−0.0019 (9)	0.0065 (8)	0.0032 (9)
C45	0.0274 (10)	0.0204 (11)	0.0155 (10)	0.0024 (8)	0.0008 (8)	0.0024 (8)
C46	0.0189 (9)	0.0198 (10)	0.0146 (10)	0.0027 (8)	0.0024 (7)	−0.0007 (8)
N1	0.0127 (7)	0.0162 (8)	0.0166 (8)	0.0007 (6)	0.0042 (6)	−0.0002 (7)
P1	0.0157 (2)	0.0163 (3)	0.0142 (3)	0.00285 (19)	0.00334 (18)	0.0017 (2)
P2	0.0146 (2)	0.0171 (3)	0.0149 (3)	0.00371 (19)	0.00380 (18)	0.0017 (2)

Geometric parameters (Å, º) top

C1—N1	1.499 (2)	C23—C24	1.388 (3)
C1—C2	1.547 (3)	C23—H23	0.95
C1—C5A	1.553 (3)	C24—C25	1.383 (3)
C1—H1	1	C24—H24	0.95
C2—C3A	1.530 (3)	C25—C26	1.393 (3)
C2—H2A	0.99	C25—H25	0.95
C2—H2B	0.99	C26—H26	0.95
C3A—C4A	1.546 (3)	C31—C36	1.396 (3)
C3A—H3A1	0.99	C31—C32	1.400 (3)
C3A—H3A2	0.99	C31—P2	1.842 (2)
C4A—C5A	1.512 (3)	C32—C33	1.390 (3)
C4A—H4A1	0.99	C32—H32	0.95
C4A—H4A2	0.99	C33—C34	1.378 (3)
C5A—H5A1	0.99	C33—H33	0.95
C5A—H5A2	0.99	C34—C35	1.394 (3)
C4B—H4B1	0.99	C34—H34	0.95
C4B—H4B2	0.99	C35—C36	1.393 (3)
C11—C16	1.392 (2)	C35—H35	0.95
C11—C12	1.400 (3)	C36—H36	0.95
C11—P1	1.847 (2)	C41—C46	1.391 (3)
C12—C13	1.381 (3)	C41—C42	1.403 (2)
C12—H12	0.95	C41—P2	1.8274 (19)
C13—C14	1.384 (3)	C42—C43	1.387 (3)
C13—H13	0.95	C42—H42	0.95
C14—C15	1.382 (3)	C43—C44	1.388 (3)
C14—H14	0.95	C43—H43	0.95
C15—C16	1.389 (3)	C44—C45	1.386 (3)
C15—H15	0.95	C44—H44	0.95
C16—H16	0.95	C45—C46	1.393 (3)
C21—C26	1.397 (3)	C45—H45	0.95
C21—C22	1.400 (3)	C46—H46	0.95
C21—P1	1.8388 (19)	N1—P1	1.7157 (17)
C22—C23	1.381 (3)	N1—P2	1.7205 (16)
C22—H22	0.95

N1—C1—C2	114.93 (14)	C22—C23—H23	120
N1—C1—C5A	113.39 (15)	C24—C23—H23	120
C2—C1—C5A	105.15 (16)	C25—C24—C23	119.51 (18)
N1—C1—H1	107.7	C25—C24—H24	120.2
C2—C1—H1	107.7	C23—C24—H24	120.2
C5A—C1—H1	107.7	C24—C25—C26	120.43 (19)
C3A—C2—C1	104.78 (16)	C24—C25—H25	119.8
C3A—C2—H2A	110.8	C26—C25—H25	119.8
C1—C2—H2A	110.8	C25—C26—C21	120.72 (19)
C3A—C2—H2B	110.8	C25—C26—H26	119.6
C1—C2—H2B	110.8	C21—C26—H26	119.6
H2A—C2—H2B	108.9	C36—C31—C32	118.66 (17)
C2—C3A—C4A	103.07 (17)	C36—C31—P2	124.46 (14)
C2—C3A—H3A1	111.1	C32—C31—P2	116.80 (14)
C4A—C3A—H3A1	111.1	C33—C32—C31	120.67 (19)
C2—C3A—H3A2	111.1	C33—C32—H32	119.7
C4A—C3A—H3A2	111.1	C31—C32—H32	119.7
H3A1—C3A—H3A2	109.1	C34—C33—C32	120.24 (19)
C5A—C4A—C3A	103.38 (19)	C34—C33—H33	119.9
C5A—C4A—H4A1	111.1	C32—C33—H33	119.9
C3A—C4A—H4A1	111.1	C33—C34—C35	119.90 (18)
C5A—C4A—H4A2	111.1	C33—C34—H34	120.1
C3A—C4A—H4A2	111.1	C35—C34—H34	120
H4A1—C4A—H4A2	109.1	C36—C35—C34	120.09 (19)
C4A—C5A—C1	107.22 (17)	C36—C35—H35	120
C4A—C5A—H5A1	110.3	C34—C35—H35	120
C1—C5A—H5A1	110.3	C35—C36—C31	120.40 (18)
C4A—C5A—H5A2	110.3	C35—C36—H36	119.8
C1—C5A—H5A2	110.3	C31—C36—H36	119.8
H5A1—C5A—H5A2	108.5	C46—C41—C42	118.29 (17)
H4B1—C4B—H4B2	108.5	C46—C41—P2	123.86 (13)
C16—C11—C12	117.63 (17)	C42—C41—P2	117.40 (14)
C16—C11—P1	125.95 (14)	C43—C42—C41	121.13 (18)
C12—C11—P1	116.41 (13)	C43—C42—H42	119.4
C13—C12—C11	121.19 (17)	C41—C42—H42	119.4
C13—C12—H12	119.4	C42—C43—C44	119.87 (18)
C11—C12—H12	119.4	C42—C43—H43	120.1
C12—C13—C14	120.32 (18)	C44—C43—H43	120.1
C12—C13—H13	119.8	C45—C44—C43	119.67 (18)
C14—C13—H13	119.8	C45—C44—H44	120.2
C15—C14—C13	119.47 (18)	C43—C44—H44	120.2
C15—C14—H14	120.3	C44—C45—C46	120.47 (18)
C13—C14—H14	120.3	C44—C45—H45	119.8
C14—C15—C16	120.17 (17)	C46—C45—H45	119.8
C14—C15—H15	119.9	C41—C46—C45	120.55 (17)
C16—C15—H15	119.9	C41—C46—H46	119.7
C15—C16—C11	121.20 (17)	C45—C46—H46	119.7
C15—C16—H16	119.4	C1—N1—P1	121.43 (12)
C11—C16—H16	119.4	C1—N1—P2	115.22 (12)
C26—C21—C22	117.78 (17)	P1—N1—P2	121.76 (9)
C26—C21—P1	124.69 (15)	N1—P1—C21	104.70 (9)
C22—C21—P1	117.13 (14)	N1—P1—C11	102.52 (8)
C23—C22—C21	121.44 (19)	C21—P1—C11	101.65 (8)
C23—C22—H22	119.3	N1—P2—C41	104.71 (8)
C21—C22—H22	119.3	N1—P2—C31	104.59 (8)
C22—C23—C24	120.10 (19)	C41—P2—C31	100.62 (9)

N1—C1—C2—C3A	145.49 (16)	C42—C43—C44—C45	0.5 (3)
C5A—C1—C2—C3A	20.08 (18)	C43—C44—C45—C46	−0.6 (3)
C1—C2—C3A—C4A	−37.2 (2)	C42—C41—C46—C45	1.1 (3)
C2—C3A—C4A—C5A	40.1 (2)	P2—C41—C46—C45	173.20 (15)
C3A—C4A—C5A—C1	−27.7 (2)	C44—C45—C46—C41	−0.2 (3)
N1—C1—C5A—C4A	−121.37 (17)	C2—C1—N1—P1	103.43 (17)
C2—C1—C5A—C4A	4.99 (19)	C5A—C1—N1—P1	−135.56 (14)
C16—C11—C12—C13	−1.8 (3)	C2—C1—N1—P2	−62.41 (19)
P1—C11—C12—C13	179.38 (16)	C5A—C1—N1—P2	58.59 (18)
C11—C12—C13—C14	1.4 (3)	C1—N1—P1—C21	59.96 (15)
C12—C13—C14—C15	−0.2 (3)	P2—N1—P1—C21	−135.12 (10)
C13—C14—C15—C16	−0.7 (3)	C1—N1—P1—C11	−45.82 (15)
C14—C15—C16—C11	0.3 (3)	P2—N1—P1—C11	119.10 (10)
C12—C11—C16—C15	0.9 (3)	C26—C21—P1—N1	8.13 (17)
P1—C11—C16—C15	179.66 (15)	C22—C21—P1—N1	−179.28 (13)
C26—C21—C22—C23	0.5 (3)	C26—C21—P1—C11	114.56 (16)
P1—C21—C22—C23	−172.64 (14)	C22—C21—P1—C11	−72.86 (15)
C21—C22—C23—C24	−0.6 (3)	C16—C11—P1—N1	112.33 (17)
C22—C23—C24—C25	−0.3 (3)	C12—C11—P1—N1	−68.92 (16)
C23—C24—C25—C26	1.3 (3)	C16—C11—P1—C21	4.20 (19)
C24—C25—C26—C21	−1.4 (3)	C12—C11—P1—C21	−177.05 (15)
C22—C21—C26—C25	0.5 (3)	C1—N1—P2—C41	−135.34 (13)
P1—C21—C26—C25	173.05 (14)	P1—N1—P2—C41	58.87 (12)
C36—C31—C32—C33	−2.2 (3)	C1—N1—P2—C31	119.28 (13)
P2—C31—C32—C33	174.66 (14)	P1—N1—P2—C31	−46.52 (12)
C31—C32—C33—C34	1.0 (3)	C46—C41—P2—N1	20.87 (18)
C32—C33—C34—C35	0.5 (3)	C42—C41—P2—N1	−166.95 (15)
C33—C34—C35—C36	−0.9 (3)	C46—C41—P2—C31	129.18 (17)
C34—C35—C36—C31	−0.4 (3)	C42—C41—P2—C31	−58.64 (17)
C32—C31—C36—C35	1.9 (3)	C36—C31—P2—N1	76.55 (16)
P2—C31—C36—C35	−174.75 (14)	C32—C31—P2—N1	−100.16 (15)
C46—C41—C42—C43	−1.2 (3)	C36—C31—P2—C41	−31.86 (17)
P2—C41—C42—C43	−173.85 (16)	C32—C31—P2—C41	151.43 (14)
C41—C42—C43—C44	0.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···P2	0.99	2.82	3.269 (2)	108
C5A—H5A1···P2	0.99	2.82	3.202 (3)	104
C12—H12···Cg1	0.95	2.72	3.667 (2)	174
C3A—H3A2···Cg1ⁱ	0.99	2.89	3.811 (2)	155

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₉NP₂
M_r	453.47
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.803 (5), 11.166 (4), 12.685 (5)
α, β, γ (°)	97.144 (4), 101.261 (5), 99.707 (5)
V (Å³)	1189.3 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.2
Crystal size (mm)	0.19 × 0.13 × 0.08

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.963, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	12794, 5817, 4333
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.106, 1.06
No. of reflections	5817
No. of parameters	293
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.33

Computer programs: APEX2 (Bruker, 2010), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···P2	0.99	2.82	3.269 (2)	108.2
C5A—H5A1···P2	0.99	2.82	3.202 (3)	103.8
C12—H12···Cg1	0.95	2.72	3.667 (2)	174.4
C3A—H3A2···Cg1ⁱ	0.99	2.89	3.811 (2)	155.4

Symmetry code: (i) x+1, y, z.

Acknowledgements

Financial assistance from the Department of Science and Technology (DST) of South Africa, the South African National Research Foundation (NRF), as well as the DST–NRF centre of excellence and the University of the Free State are gratefully acknowledged.

References

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Volume 66| Part 12| December 2010| Pages o3322-o3323

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