N,N-Bis(diphenyl-phosphan-yl)cyclo-butanamine.

In the title compound, C(28)H(27)NP(2), 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 intra-molecular C-H⋯P hydrogen bond occurs. In the crystal, inter-molecular C-H⋯π inter-actions link the mol-ecules into a supra-molecular 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 (n class="Gene">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 = 439.45

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.064

S = 1.04

3035 reflections

281 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAIn class="Chemical">NT-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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027656/go2019sup1.cif

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

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

C28H27NP2	F(000) = 464
Mr = 439.45	Dx = 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

Bruker X8 APEXII 4K KappaCCD diffractometer	3035 independent reflections
Radiation source: fine-focus sealed tube	2930 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω and φ scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.937, Tmax = 0.992	k = −12→12
20748 measured reflections	l = −16→16

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(Fo2) + (0.0386P)2 + 0.1935P] where P = (Fo2 + 2Fc2)/3
3035 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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.

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) ; (ii) .