N,N-Bis(diphenyl­phosphan­yl)cyclo­butanamine

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

doi:10.1107/S1600536811027656

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages o2041-o2042

doi:10.1107/S1600536811027656

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N,N-Bis(diphenylphosphanyl)cyclobutanamine

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 6 July 2011; accepted 11 July 2011; online 16 July 2011)

In the title compound, C₂₈H₂₇NP₂, the N atom adopts an almost planar geometry with the two P atoms and the C atom attached to it, with a distance of 0.066 (2) Å between the N atom and the C/P/P plane. The distorted trigonal–pyramidal geometry of the N atom is further illustrated by bond angles ranging between 115.22 (11) and 123.53 (8)°. Bond angles varying from 99.99 (9) to 108.07 (9) ° are indicative of the distorted pyramidal environment around the P atoms. An intramolecular C—H⋯P hydrogen bond occurs. In the crystal, intermolecular C—H⋯π interactions link the molecules into a supramolecular 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. (2010a ,b ). For diphosphinoamine (PNP) and other P-donor ligands, see: Muller et al. (2008 ); Purcell et al. (1995 ); Otto & Roodt (2001 ); Otto et al. (2005 ). For their use in catalytic olefin transformation reactions, see: Haumann et al. (2004 ); Crous et al. (2005 ); Booyens et al. (2007 ); Cloete et al. (2011 ); Ferreira et al. (2007 ).

Experimental

Crystal data

C₂₈H₂₇NP₂
M_r = 439.45
Monoclinic, P 2₁
a = 9.414 (5) Å
b = 9.664 (5) Å
c = 12.644 (4) Å
β = 94.245 (5)°
V = 1147.2 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.32 × 0.12 × 0.04 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.937, T_max = 0.992
20748 measured reflections
3035 independent reflections
2930 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.064
S = 1.04
3035 reflections
281 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C32—H32⋯P1	0.95	2.8	3.452 (2)	127
C43—H43⋯Cg1ⁱ	0.95	2.87	3.686 (7)	144
C44—H44⋯Cg2ⁱⁱ	0.95	2.81	3.614 (6)	143
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

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: 10.1107/S1600536811027656/go2019sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027656/go2019Isup2.hkl

checkCIF report

Comment top

Diphosphinoamine (PNP) and other P donor ligands (Muller et al., 2008; Purcell et al., 1995; Otto et al., 2005; Otto & Roodt, 2001) with various substituents on both the P and N atoms form part of ongoing research in different catalytic olefin transformation reactions such as hydroformylation (Haumann et al., 2004; Crous et al., 2005), metathesis (Booyens et al.) methoxycarbonylation (Ferreira et al., 2007) and tetramerization (Cloete et al., 2011). In the title compound, C₂₉H₂₉NP₂, Fig.1, 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., 2010a, 2010b).

The N(P₂C) group is almost planar, with the central N displaced by -0.066 (2) Å from the P1—P2—C1 plane. The distorted trigonal-pyramidal geometry around the N atom is evident by the bond angles ranging between 115.22 (11) and 123.53 (8) °. The distorted triangular pyramidal geometry around the phosphorous atoms is indicated by C—P—C angles varying from 99.99 (9) - 108.07 (9) ° and N—P—C angles from 102.24 (8) - 108.07 (9) °. The phosphorous lone pairs are trans with respect to the N—C bond, therefore the title compound has a C_s conformer in the solid state. The crystal packing is stabilized by a C—H···P intramolecular hydrogen bond (Table 1) and intermolecular C—H···π interactions resulting in a three-dimensional network (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. (2010a,b). For diphosphinoamine (PNP) and other P-donor ligands, see: Muller et al. (2008); Purcell et al. (1995); Otto & Roodt (2001); Otto et al. (2005). For their use in catalytic olefin transformation reactions, see: Haumann et al. (2004); Crous et al. (2005); Booyens et al. (2007); Cloete et al. (2011); Ferreira et al. (2007).

Experimental top

Cyclobutylamine (0.010 mol, 854 µl) 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: 2.100 g, 48%)

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.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis forming the three-dimensional framework. C—H···π interactions are shown as dashed lines. Displacement ellipsoids are drawn at the 50% probability level.

N,N-Bis(diphenylphosphanyl)cyclobutanamine top

Crystal data top

C₂₈H₂₇NP₂	F(000) = 464
M_r = 439.45	D_x = 1.272 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9952 reflections
a = 9.414 (5) Å	θ = 2.7–28.3°
b = 9.664 (5) Å	µ = 0.21 mm⁻¹
c = 12.644 (4) Å	T = 100 K
β = 94.245 (5)°	Cuboid, colourless
V = 1147.2 (10) Å³	0.32 × 0.12 × 0.04 mm
Z = 2

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	3035 independent reflections
Radiation source: fine-focus sealed tube	2930 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 28.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.937, T_max = 0.992	k = −12→12
20748 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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0386P)² + 0.1935P] where P = (F_o² + 2F_c²)/3
3035 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₈H₂₇NP₂	V = 1147.2 (10) Å³
M_r = 439.45	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.414 (5) Å	µ = 0.21 mm⁻¹
b = 9.664 (5) Å	T = 100 K
c = 12.644 (4) Å	0.32 × 0.12 × 0.04 mm
β = 94.245 (5)°

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	3035 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2930 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.992	R_int = 0.027
20748 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	1 restraint
wR(F²) = 0.064	H-atom parameters constrained
S = 1.04	Δρ_max = 0.25 e Å⁻³
3035 reflections	Δρ_min = −0.18 e Å⁻³
281 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 40 s/frame. A total of 1709 frames were collected with a frame width of 0.5° covering up to θ = 28.39° with 99.9% completeness accomplished.

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
C1	0.63564 (17)	0.73665 (19)	0.12318 (13)	0.0161 (3)
H1	0.7182	0.7791	0.1657	0.019*
C2	0.6829 (2)	0.5945 (2)	0.08102 (15)	0.0227 (4)
H2A	0.7631	0.5515	0.1244	0.027*
H2B	0.6039	0.528	0.0666	0.027*
C3	0.72812 (19)	0.6710 (2)	−0.01884 (14)	0.0243 (4)
H3A	0.8308	0.694	−0.016	0.029*
H3B	0.697	0.6245	−0.0864	0.029*
C4	0.63230 (18)	0.7937 (2)	0.00897 (13)	0.0202 (3)
H4A	0.6781	0.8854	0.0035	0.024*
H4B	0.5366	0.7926	−0.0291	0.024*
C11	0.61059 (17)	0.96900 (19)	0.30492 (14)	0.0170 (3)
C12	0.59621 (18)	1.04878 (19)	0.21255 (13)	0.0185 (3)
H12	0.5452	1.0127	0.151	0.022*
C13	0.65569 (17)	1.1803 (2)	0.20966 (14)	0.0207 (3)
H13	0.6468	1.2325	0.1458	0.025*
C14	0.72805 (19)	1.2358 (2)	0.29965 (16)	0.0238 (4)
H14	0.7687	1.3257	0.2977	0.029*
C15	0.7403 (2)	1.1586 (2)	0.39223 (15)	0.0259 (4)
H15	0.7887	1.1963	0.4542	0.031*
C16	0.68275 (19)	1.0269 (2)	0.39524 (14)	0.0223 (4)
H16	0.6923	0.9752	0.4593	0.027*
C21	0.67262 (18)	0.69892 (19)	0.37827 (13)	0.0177 (3)
C22	0.81721 (19)	0.7224 (2)	0.36534 (13)	0.0204 (3)
H22	0.845	0.7973	0.3228	0.024*
C23	0.9200 (2)	0.6362 (2)	0.41469 (14)	0.0249 (4)
H23	1.0179	0.6522	0.4053	0.03*
C24	0.8808 (2)	0.5268 (2)	0.47773 (14)	0.0283 (4)
H24	0.9515	0.4673	0.5103	0.034*
C25	0.7388 (2)	0.5049 (2)	0.49284 (14)	0.0270 (4)
H25	0.7118	0.431	0.5366	0.032*
C26	0.6354 (2)	0.5909 (2)	0.44406 (14)	0.0216 (4)
H26	0.5381	0.5759	0.4556	0.026*
C31	0.21248 (16)	0.8079 (2)	0.13397 (12)	0.0165 (3)
C32	0.17680 (19)	0.8748 (2)	0.22612 (14)	0.0227 (4)
H32	0.232	0.8584	0.2909	0.027*
C33	0.0619 (2)	0.9650 (2)	0.22457 (16)	0.0249 (4)
H33	0.0406	1.0117	0.2876	0.03*
C34	−0.02202 (19)	0.9870 (2)	0.13090 (16)	0.0241 (4)
H34	−0.1016	1.0474	0.13	0.029*
C35	0.0110 (2)	0.9203 (2)	0.03906 (15)	0.0251 (4)
H35	−0.0464	0.9348	−0.025	0.03*
C36	0.12781 (18)	0.8322 (2)	0.04019 (13)	0.0206 (4)
H36	0.1504	0.7879	−0.0235	0.025*
C41	0.30058 (17)	0.54508 (18)	0.21428 (12)	0.0156 (3)
C42	0.40188 (18)	0.45205 (19)	0.25833 (14)	0.0188 (3)
H42	0.4998	0.467	0.2484	0.023*
C43	0.3623 (2)	0.33809 (19)	0.31634 (14)	0.0219 (4)
H43	0.4331	0.2773	0.3472	0.026*
C44	0.2191 (2)	0.3130 (2)	0.32932 (14)	0.0244 (4)
H44	0.1914	0.2351	0.3687	0.029*
C45	0.11719 (19)	0.4034 (2)	0.28400 (15)	0.0250 (4)
H45	0.0191	0.3861	0.2915	0.03*
C46	0.15723 (19)	0.5188 (2)	0.22774 (14)	0.0208 (3)
H46	0.0864	0.5804	0.1982	0.025*
N1	0.50881 (15)	0.74590 (16)	0.18514 (11)	0.0153 (3)
P1	0.52394 (4)	0.79965 (6)	0.31465 (3)	0.01550 (9)
P2	0.35464 (4)	0.67934 (6)	0.12377 (3)	0.01489 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0156 (7)	0.0166 (7)	0.0163 (7)	0.0007 (6)	0.0022 (6)	−0.0001 (6)
C2	0.0231 (9)	0.0179 (8)	0.0279 (9)	0.0032 (7)	0.0082 (7)	−0.0003 (7)
C3	0.0249 (9)	0.0246 (9)	0.0245 (8)	−0.0014 (8)	0.0089 (7)	−0.0050 (8)
C4	0.0210 (8)	0.0228 (8)	0.0173 (7)	0.0008 (7)	0.0048 (6)	0.0025 (7)
C11	0.0123 (7)	0.0168 (8)	0.0217 (8)	0.0012 (6)	0.0006 (6)	−0.0022 (6)
C12	0.0183 (8)	0.0190 (8)	0.0181 (8)	0.0025 (6)	0.0006 (6)	−0.0033 (6)
C13	0.0183 (8)	0.0195 (8)	0.0247 (8)	0.0016 (7)	0.0034 (6)	0.0009 (7)
C14	0.0177 (8)	0.0173 (8)	0.0362 (10)	−0.0002 (7)	0.0007 (7)	−0.0030 (7)
C15	0.0217 (9)	0.0242 (10)	0.0301 (9)	0.0021 (7)	−0.0095 (7)	−0.0062 (8)
C16	0.0239 (9)	0.0222 (9)	0.0200 (8)	0.0037 (7)	−0.0037 (7)	−0.0016 (7)
C21	0.0202 (8)	0.0185 (8)	0.0142 (7)	0.0002 (7)	−0.0006 (6)	−0.0007 (6)
C22	0.0218 (8)	0.0218 (9)	0.0173 (8)	0.0007 (7)	−0.0007 (6)	−0.0004 (6)
C23	0.0221 (9)	0.0314 (10)	0.0206 (8)	0.0062 (7)	−0.0020 (7)	−0.0047 (7)
C24	0.0395 (11)	0.0248 (10)	0.0194 (8)	0.0130 (9)	−0.0074 (8)	−0.0038 (7)
C25	0.0448 (12)	0.0197 (9)	0.0156 (8)	0.0007 (8)	−0.0026 (7)	0.0019 (7)
C26	0.0278 (9)	0.0201 (8)	0.0166 (8)	−0.0038 (7)	−0.0006 (7)	−0.0003 (7)
C31	0.0139 (7)	0.0158 (7)	0.0197 (7)	−0.0015 (6)	0.0009 (6)	0.0011 (7)
C32	0.0213 (8)	0.0258 (9)	0.0206 (8)	0.0038 (7)	−0.0018 (7)	−0.0017 (7)
C33	0.0232 (9)	0.0237 (9)	0.0282 (9)	0.0033 (7)	0.0049 (7)	−0.0031 (7)
C34	0.0164 (8)	0.0206 (9)	0.0356 (10)	0.0017 (7)	0.0039 (7)	0.0055 (8)
C35	0.0207 (8)	0.0276 (10)	0.0262 (9)	−0.0003 (7)	−0.0038 (7)	0.0071 (8)
C36	0.0192 (8)	0.0239 (9)	0.0186 (8)	−0.0018 (6)	0.0001 (6)	0.0006 (6)
C41	0.0180 (8)	0.0145 (7)	0.0144 (7)	−0.0018 (6)	0.0017 (6)	−0.0027 (6)
C42	0.0164 (8)	0.0185 (8)	0.0216 (8)	0.0000 (6)	0.0025 (6)	−0.0016 (6)
C43	0.0242 (9)	0.0194 (9)	0.0223 (8)	0.0017 (7)	0.0026 (7)	0.0018 (7)
C44	0.0297 (9)	0.0185 (8)	0.0257 (8)	−0.0056 (8)	0.0074 (7)	0.0011 (7)
C45	0.0187 (8)	0.0247 (9)	0.0323 (10)	−0.0052 (7)	0.0073 (7)	−0.0018 (8)
C46	0.0181 (8)	0.0212 (8)	0.0231 (8)	−0.0006 (7)	0.0010 (6)	−0.0014 (7)
N1	0.0135 (6)	0.0178 (7)	0.0146 (6)	−0.0015 (5)	0.0012 (5)	−0.0021 (5)
P1	0.01451 (19)	0.0175 (2)	0.01444 (18)	−0.00069 (16)	0.00074 (14)	−0.00094 (16)
P2	0.01521 (19)	0.01517 (18)	0.01420 (18)	−0.00057 (16)	0.00048 (13)	−0.00147 (16)

Geometric parameters (Å, º) top

C1—N1	1.478 (2)	C24—C25	1.380 (3)
C1—C4	1.544 (2)	C24—H24	0.95
C1—C2	1.551 (2)	C25—C26	1.389 (3)
C1—H1	1	C25—H25	0.95
C2—C3	1.550 (3)	C26—H26	0.95
C2—H2A	0.99	C31—C32	1.395 (2)
C2—H2B	0.99	C31—C36	1.399 (2)
C3—C4	1.546 (3)	C31—P2	1.838 (2)
C3—H3A	0.99	C32—C33	1.388 (3)
C3—H3B	0.99	C32—H32	0.95
C4—H4A	0.99	C33—C34	1.390 (3)
C4—H4B	0.99	C33—H33	0.95
C11—C12	1.398 (2)	C34—C35	1.383 (3)
C11—C16	1.401 (2)	C34—H34	0.95
C11—P1	1.837 (2)	C35—C36	1.390 (3)
C12—C13	1.391 (3)	C35—H35	0.95
C12—H12	0.95	C36—H36	0.95
C13—C14	1.390 (3)	C41—C46	1.396 (2)
C13—H13	0.95	C41—C42	1.396 (2)
C14—C15	1.386 (3)	C41—P2	1.8271 (19)
C14—H14	0.95	C42—C43	1.389 (2)
C15—C16	1.384 (3)	C42—H42	0.95
C15—H15	0.95	C43—C44	1.391 (3)
C16—H16	0.95	C43—H43	0.95
C21—C26	1.396 (2)	C44—C45	1.389 (3)
C21—C22	1.401 (3)	C44—H44	0.95
C21—P1	1.8404 (19)	C45—C46	1.390 (3)
C22—C23	1.389 (3)	C45—H45	0.95
C22—H22	0.95	C46—H46	0.95
C23—C24	1.390 (3)	N1—P1	1.7138 (15)
C23—H23	0.95	N1—P2	1.7192 (16)

N1—C1—C4	120.84 (14)	C23—C24—H24	120.1
N1—C1—C2	119.96 (14)	C24—C25—C26	120.05 (18)
C4—C1—C2	88.95 (13)	C24—C25—H25	120
N1—C1—H1	108.5	C26—C25—H25	120
C4—C1—H1	108.5	C25—C26—C21	120.91 (18)
C2—C1—H1	108.5	C25—C26—H26	119.5
C3—C2—C1	87.72 (14)	C21—C26—H26	119.5
C3—C2—H2A	114	C32—C31—C36	118.23 (16)
C1—C2—H2A	114	C32—C31—P2	126.41 (13)
C3—C2—H2B	114	C36—C31—P2	115.22 (13)
C1—C2—H2B	114	C33—C32—C31	120.98 (17)
H2A—C2—H2B	111.2	C33—C32—H32	119.5
C4—C3—C2	88.91 (13)	C31—C32—H32	119.5
C4—C3—H3A	113.8	C32—C33—C34	120.06 (18)
C2—C3—H3A	113.8	C32—C33—H33	120
C4—C3—H3B	113.8	C34—C33—H33	120
C2—C3—H3B	113.8	C35—C34—C33	119.69 (17)
H3A—C3—H3B	111.1	C35—C34—H34	120.2
C1—C4—C3	88.10 (13)	C33—C34—H34	120.2
C1—C4—H4A	114	C34—C35—C36	120.21 (17)
C3—C4—H4A	114	C34—C35—H35	119.9
C1—C4—H4B	114	C36—C35—H35	119.9
C3—C4—H4B	114	C35—C36—C31	120.80 (17)
H4A—C4—H4B	111.2	C35—C36—H36	119.6
C12—C11—C16	118.15 (17)	C31—C36—H36	119.6
C12—C11—P1	122.11 (13)	C46—C41—C42	118.17 (16)
C16—C11—P1	119.48 (14)	C46—C41—P2	121.48 (13)
C13—C12—C11	120.80 (16)	C42—C41—P2	119.57 (13)
C13—C12—H12	119.6	C43—C42—C41	121.28 (16)
C11—C12—H12	119.6	C43—C42—H42	119.4
C14—C13—C12	120.33 (17)	C41—C42—H42	119.4
C14—C13—H13	119.8	C42—C43—C44	120.01 (17)
C12—C13—H13	119.8	C42—C43—H43	120
C15—C14—C13	119.28 (18)	C44—C43—H43	120
C15—C14—H14	120.4	C45—C44—C43	119.19 (17)
C13—C14—H14	120.4	C45—C44—H44	120.4
C16—C15—C14	120.65 (17)	C43—C44—H44	120.4
C16—C15—H15	119.7	C44—C45—C46	120.68 (17)
C14—C15—H15	119.7	C44—C45—H45	119.7
C15—C16—C11	120.78 (18)	C46—C45—H45	119.7
C15—C16—H16	119.6	C45—C46—C41	120.65 (17)
C11—C16—H16	119.6	C45—C46—H46	119.7
C26—C21—C22	118.63 (16)	C41—C46—H46	119.7
C26—C21—P1	116.11 (14)	C1—N1—P1	120.76 (11)
C22—C21—P1	125.26 (13)	C1—N1—P2	115.22 (11)
C23—C22—C21	120.07 (17)	P1—N1—P2	123.53 (8)
C23—C22—H22	120	N1—P1—C11	102.24 (8)
C21—C22—H22	120	N1—P1—C21	105.31 (8)
C22—C23—C24	120.50 (18)	C11—P1—C21	99.99 (9)
C22—C23—H23	119.7	N1—P2—C41	104.36 (7)
C24—C23—H23	119.8	N1—P2—C31	108.07 (9)
C25—C24—C23	119.79 (17)	C41—P2—C31	101.44 (8)
C25—C24—H24	120.1

N1—C1—C2—C3	144.39 (15)	C42—C43—C44—C45	−0.2 (3)
C4—C1—C2—C3	18.85 (13)	C43—C44—C45—C46	−1.0 (3)
C1—C2—C3—C4	−18.83 (13)	C44—C45—C46—C41	1.0 (3)
N1—C1—C4—C3	−143.70 (15)	C42—C41—C46—C45	0.3 (3)
C2—C1—C4—C3	−18.90 (13)	P2—C41—C46—C45	170.16 (14)
C2—C3—C4—C1	18.91 (14)	C4—C1—N1—P1	−134.56 (15)
C16—C11—C12—C13	1.9 (2)	C2—C1—N1—P1	116.81 (15)
P1—C11—C12—C13	175.95 (13)	C4—C1—N1—P2	53.23 (19)
C11—C12—C13—C14	−1.4 (2)	C2—C1—N1—P2	−55.39 (19)
C12—C13—C14—C15	0.0 (3)	C1—N1—P1—C11	55.96 (14)
C13—C14—C15—C16	0.7 (3)	P2—N1—P1—C11	−132.50 (11)
C14—C15—C16—C11	−0.1 (3)	C1—N1—P1—C21	−48.12 (15)
C12—C11—C16—C15	−1.2 (3)	P2—N1—P1—C21	123.42 (11)
P1—C11—C16—C15	−175.36 (14)	C12—C11—P1—N1	26.64 (15)
C26—C21—C22—C23	2.1 (3)	C16—C11—P1—N1	−159.40 (14)
P1—C21—C22—C23	−177.74 (14)	C12—C11—P1—C21	134.85 (14)
C21—C22—C23—C24	−0.4 (3)	C16—C11—P1—C21	−51.19 (15)
C22—C23—C24—C25	−1.0 (3)	C26—C21—P1—N1	−104.69 (14)
C23—C24—C25—C26	0.8 (3)	C22—C21—P1—N1	75.13 (17)
C24—C25—C26—C21	0.9 (3)	C26—C21—P1—C11	149.56 (13)
C22—C21—C26—C25	−2.3 (3)	C22—C21—P1—C11	−30.62 (17)
P1—C21—C26—C25	177.53 (14)	C1—N1—P2—C41	121.40 (12)
C36—C31—C32—C33	−1.1 (3)	P1—N1—P2—C41	−50.57 (14)
P2—C31—C32—C33	−176.59 (15)	C1—N1—P2—C31	−131.22 (12)
C31—C32—C33—C34	1.8 (3)	P1—N1—P2—C31	56.81 (13)
C32—C33—C34—C35	−1.0 (3)	C46—C41—P2—N1	144.79 (14)
C33—C34—C35—C36	−0.3 (3)	C42—C41—P2—N1	−45.52 (15)
C34—C35—C36—C31	0.9 (3)	C46—C41—P2—C31	32.56 (16)
C32—C31—C36—C35	−0.2 (3)	C42—C41—P2—C31	−157.75 (13)
P2—C31—C36—C35	175.78 (14)	C32—C31—P2—N1	−50.48 (18)
C46—C41—C42—C43	−1.6 (2)	C36—C31—P2—N1	133.95 (13)
P2—C41—C42—C43	−171.62 (13)	C32—C31—P2—C41	58.92 (17)
C41—C42—C43—C44	1.6 (3)	C36—C31—P2—C41	−116.66 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···P1	0.95	2.8	3.452 (2)	127
C43—H43···Cg1ⁱ	0.95	2.87	3.686 (7)	144
C44—H44···Cg2ⁱⁱ	0.95	2.81	3.614 (6)	143

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₇NP₂
M_r	439.45
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	9.414 (5), 9.664 (5), 12.644 (4)
β (°)	94.245 (5)
V (Å³)	1147.2 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.32 × 0.12 × 0.04

Data collection
Diffractometer	Bruker X8 APEXII 4K KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.937, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	20748, 3035, 2930
R_int	0.027

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.064, 1.04
No. of reflections	3035
No. of parameters	281
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.18

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 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···P1	0.95	2.8	3.452 (2)	126.6
C43—H43···Cg1ⁱ	0.95	2.87	3.686 (7)	144
C44—H44···Cg2ⁱⁱ	0.95	2.81	3.614 (6)	142.6

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1.

Acknowledgements

Financial assistance from the Department of Science and Technology (DST) of South Africa, the South African National Research Foundation (NRF), the DST–NRF centre of excellence (c*change), the University of the Free State and the INKABA funding project are gratefully acknowledged.

References

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Volume 67| Part 8| August 2011| Pages o2041-o2042

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