N,N-Bis(diphenyl-phosphino)ethyl-amine.

In the title compound, C(26)H(25)NP(2), the diphenyl-phosphino groups are staggered relative to the PNP backbone, even though the ethyl substituent coordinated to the N atom is not sterically bulky. The N atom adapts an almost planar geometry with two P atoms and a C atom of the allyl group attached to it in order to accommodate the steric bulk of the phenyl groups and the alkyl group. The distortion of the trigonal-pyramidal geometry of the nitro-gen is further illustrated by the bond angles which range between 114.0 (1) and 123.7 (1)°. There are no classical inter-molecular inter-actions.

Related literature

For similar diphosphineamine non-coordinated ligands with the P—N—P angle ranging between 113.3 (2) and 122.8 (3)°, see: Keat et al. (1981 ▶); Cotton et al. (1996 ▶); Fei et al. (2003 ▶); Cloete et al. (2008 ▶).

Experimental

Crystal data

C26H25NP2

M = 413.44

Monoclinic,

a = 9.570 (5) Å

b = 13.441 (5) Å

c = 16.907 (5) Å

β = 91.647 (5)°

V = 2173.9 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 101 K

0.39 × 0.13 × 0.11 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.964, T max = 0.975

25117 measured reflections

5401 independent reflections

4293 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.094

S = 1.06

5401 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SIR97 (Altomare et al., 1999 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045978/pv2223sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045978/pv2223Isup2.hkl

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

C26H25NP2	F(000) = 872
Mr = 413.44	Dx = 1.263 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 5486 reflections
a = 9.570 (5) Å	θ = 2.6–27.9°
b = 13.441 (5) Å	µ = 0.21 mm−1
c = 16.907 (5) Å	T = 101 K
β = 91.647 (5)°	Needle, colourless
V = 2173.9 (15) Å3	0.39 × 0.13 × 0.11 mm
Z = 4

Bruker X8 APEXII 4K Kappa CCD diffractometer	4293 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.046
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θmax = 28.3°, θmin = 1.9°
Tmin = 0.964, Tmax = 0.975	h = −12→12
25117 measured reflections	k = −17→17
5401 independent reflections	l = −22→22

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0363P)2 + 0.8849P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.43 e Å−3
5401 reflections	Δρmin = −0.26 e Å−3
262 parameters

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.

	x	y	z	Uiso*/Ueq
N1	0.35096 (13)	0.21232 (9)	0.71479 (7)	0.0155 (3)
P1	0.41307 (4)	0.09328 (3)	0.72417 (2)	0.01616 (10)
P2	0.29406 (4)	0.26318 (3)	0.62672 (2)	0.01542 (10)
C1	0.34840 (16)	0.28240 (11)	0.78268 (8)	0.0177 (3)
H1A	0.3953	0.3451	0.7678	0.021*
H1B	0.402	0.2532	0.8279	0.021*
C2	0.20138 (17)	0.30599 (14)	0.80843 (9)	0.0250 (4)
H2A	0.2059	0.3523	0.8532	0.037*
H2B	0.1551	0.2445	0.8245	0.037*
H2C	0.1483	0.3364	0.7643	0.037*
C11	0.32088 (16)	0.04094 (11)	0.80923 (9)	0.0174 (3)
C12	0.22044 (17)	−0.03189 (12)	0.79329 (9)	0.0201 (3)
H12	0.2041	−0.0532	0.7403	0.024*
C13	0.14338 (17)	−0.07416 (12)	0.85343 (10)	0.0230 (3)
H13A	0.0756	−0.1239	0.8413	0.028*
C14	0.16600 (17)	−0.04328 (12)	0.93092 (9)	0.0234 (4)
H14	0.1126	−0.0708	0.972	0.028*
C15	0.26699 (17)	0.02804 (12)	0.94820 (9)	0.0231 (4)
H15	0.2832	0.0488	1.0014	0.028*
C16	0.34485 (17)	0.06956 (12)	0.88827 (9)	0.0206 (3)
H16	0.4147	0.1176	0.901	0.025*
C21	0.58795 (16)	0.11232 (11)	0.76925 (8)	0.0169 (3)
C22	0.65088 (16)	0.03565 (12)	0.81394 (9)	0.0193 (3)
H22	0.5985	−0.0224	0.8252	0.023*
C23	0.78758 (16)	0.04296 (12)	0.84186 (9)	0.0203 (3)
H23	0.8288	−0.0104	0.8711	0.024*
C24	0.86469 (17)	0.12790 (13)	0.82738 (9)	0.0215 (3)
H24	0.958	0.1337	0.8475	0.026*
C25	0.80438 (17)	0.20455 (12)	0.78320 (9)	0.0220 (3)
H25	0.8568	0.263	0.7732	0.026*
C26	0.66815 (16)	0.19654 (12)	0.75358 (9)	0.0196 (3)
H26	0.629	0.2488	0.7223	0.024*
C31	0.13695 (15)	0.19368 (11)	0.59763 (8)	0.0167 (3)
C32	0.07951 (17)	0.20898 (13)	0.52136 (9)	0.0222 (3)
H32	0.1242	0.2531	0.4862	0.027*
C33	−0.04139 (18)	0.16056 (14)	0.49693 (10)	0.0279 (4)
H33	−0.078	0.1704	0.4447	0.034*
C34	−0.10978 (18)	0.09766 (13)	0.54801 (10)	0.0277 (4)
H34	−0.1927	0.0642	0.5309	0.033*
C35	−0.05620 (17)	0.08398 (13)	0.62401 (10)	0.0248 (4)
H35	−0.1032	0.0417	0.6595	0.03*
C36	0.06593 (16)	0.13174 (12)	0.64867 (9)	0.0196 (3)
H36	0.1015	0.122	0.7011	0.024*
C41	0.41629 (16)	0.21875 (11)	0.55304 (8)	0.0161 (3)
C42	0.52940 (16)	0.28007 (12)	0.53709 (9)	0.0205 (3)
H42	0.5438	0.3394	0.5668	0.025*
C43	0.62142 (17)	0.25524 (13)	0.47801 (10)	0.0247 (4)
H43	0.6984	0.2974	0.4676	0.03*
C44	0.60062 (17)	0.16908 (13)	0.43447 (9)	0.0234 (4)
H44	0.6631	0.1524	0.3939	0.028*
C45	0.48928 (17)	0.10702 (12)	0.44978 (9)	0.0201 (3)
H45	0.4755	0.0477	0.42	0.024*
C46	0.39761 (16)	0.13181 (12)	0.50904 (9)	0.0184 (3)
H46	0.3214	0.089	0.5196	0.022*

	U11	U22	U33	U12	U13	U23
N1	0.0194 (6)	0.0161 (6)	0.0110 (6)	0.0014 (5)	−0.0010 (5)	−0.0018 (5)
P1	0.0210 (2)	0.01536 (19)	0.01218 (18)	−0.00001 (16)	0.00139 (15)	−0.00045 (14)
P2	0.0176 (2)	0.0164 (2)	0.01224 (18)	0.00027 (15)	0.00057 (15)	−0.00007 (14)
C1	0.0223 (8)	0.0177 (7)	0.0130 (7)	0.0001 (6)	−0.0008 (6)	−0.0030 (6)
C2	0.0246 (9)	0.0316 (9)	0.0187 (8)	0.0050 (7)	0.0009 (7)	−0.0062 (7)
C11	0.0200 (8)	0.0170 (7)	0.0152 (7)	0.0025 (6)	0.0012 (6)	0.0014 (6)
C12	0.0239 (8)	0.0180 (8)	0.0185 (7)	0.0004 (6)	−0.0001 (6)	−0.0010 (6)
C13	0.0209 (8)	0.0202 (8)	0.0280 (8)	−0.0029 (7)	0.0021 (7)	0.0012 (7)
C14	0.0227 (8)	0.0242 (8)	0.0238 (8)	0.0040 (7)	0.0080 (7)	0.0053 (7)
C15	0.0288 (9)	0.0249 (9)	0.0159 (7)	0.0021 (7)	0.0045 (7)	0.0009 (6)
C16	0.0245 (8)	0.0207 (8)	0.0165 (7)	−0.0019 (7)	0.0004 (6)	0.0002 (6)
C21	0.0197 (8)	0.0190 (7)	0.0122 (7)	0.0023 (6)	0.0042 (6)	−0.0009 (6)
C22	0.0236 (8)	0.0170 (8)	0.0176 (7)	0.0008 (6)	0.0046 (6)	0.0004 (6)
C23	0.0226 (8)	0.0223 (8)	0.0161 (7)	0.0062 (7)	0.0047 (6)	0.0030 (6)
C24	0.0166 (8)	0.0264 (8)	0.0217 (8)	0.0028 (7)	0.0031 (6)	0.0004 (7)
C25	0.0203 (8)	0.0205 (8)	0.0254 (8)	−0.0004 (6)	0.0068 (7)	0.0029 (7)
C26	0.0211 (8)	0.0198 (8)	0.0183 (7)	0.0037 (6)	0.0050 (6)	0.0035 (6)
C31	0.0162 (7)	0.0191 (7)	0.0148 (7)	0.0029 (6)	0.0003 (6)	−0.0018 (6)
C32	0.0198 (8)	0.0309 (9)	0.0159 (7)	0.0022 (7)	0.0006 (6)	0.0031 (6)
C33	0.0218 (9)	0.0420 (11)	0.0197 (8)	0.0015 (8)	−0.0055 (7)	−0.0016 (7)
C34	0.0195 (8)	0.0311 (10)	0.0323 (9)	−0.0035 (7)	−0.0039 (7)	−0.0043 (8)
C35	0.0221 (8)	0.0249 (9)	0.0274 (9)	−0.0031 (7)	0.0025 (7)	0.0013 (7)
C36	0.0184 (8)	0.0235 (8)	0.0169 (7)	0.0018 (6)	−0.0005 (6)	−0.0004 (6)
C41	0.0173 (7)	0.0195 (7)	0.0114 (6)	0.0021 (6)	−0.0006 (6)	0.0024 (6)
C42	0.0191 (8)	0.0228 (8)	0.0193 (7)	−0.0019 (6)	−0.0012 (6)	0.0011 (6)
C43	0.0180 (8)	0.0301 (9)	0.0262 (8)	−0.0014 (7)	0.0049 (7)	0.0053 (7)
C44	0.0198 (8)	0.0344 (10)	0.0159 (7)	0.0093 (7)	0.0031 (6)	0.0063 (7)
C45	0.0236 (8)	0.0235 (8)	0.0132 (7)	0.0073 (7)	−0.0007 (6)	−0.0007 (6)
C46	0.0186 (8)	0.0203 (8)	0.0164 (7)	−0.0002 (6)	0.0012 (6)	0.0017 (6)

N1—C1	1.4856 (18)	C23—H23	0.95
N1—P1	1.7127 (14)	C24—C25	1.388 (2)
N1—P2	1.7130 (13)	C24—H24	0.95
P1—C21	1.8369 (18)	C25—C26	1.387 (2)
P1—C11	1.8478 (15)	C25—H25	0.95
P2—C31	1.8255 (17)	C26—H26	0.95
P2—C41	1.8331 (16)	C31—C36	1.391 (2)
C1—C2	1.518 (2)	C31—C32	1.402 (2)
C1—H1A	0.99	C32—C33	1.380 (2)
C1—H1B	0.99	C32—H32	0.95
C2—H2A	0.98	C33—C34	1.386 (2)
C2—H2B	0.98	C33—H33	0.95
C2—H2C	0.98	C34—C35	1.382 (2)
C11—C12	1.393 (2)	C34—H34	0.95
C11—C16	1.403 (2)	C35—C36	1.387 (2)
C12—C13	1.394 (2)	C35—H35	0.95
C12—H12	0.95	C36—H36	0.95
C13—C14	1.385 (2)	C41—C42	1.393 (2)
C13—H13A	0.95	C41—C46	1.394 (2)
C14—C15	1.386 (2)	C42—C43	1.391 (2)
C14—H14	0.95	C42—H42	0.95
C15—C16	1.392 (2)	C43—C44	1.384 (2)
C15—H15	0.95	C43—H43	0.95
C16—H16	0.95	C44—C45	1.383 (2)
C21—C26	1.397 (2)	C44—H44	0.95
C21—C22	1.403 (2)	C45—C46	1.391 (2)
C22—C23	1.382 (2)	C45—H45	0.95
C22—H22	0.95	C46—H46	0.95
C23—C24	1.385 (2)
C1—N1—P1	122.29 (10)	C24—C23—H23	119.9
C1—N1—P2	114.00 (10)	C23—C24—C25	119.44 (16)
P1—N1—P2	123.65 (7)	C23—C24—H24	120.3
N1—P1—C21	102.58 (7)	C25—C24—H24	120.3
N1—P1—C11	104.81 (7)	C26—C25—C24	120.55 (15)
C21—P1—C11	100.36 (7)	C26—C25—H25	119.7
N1—P2—C31	105.59 (7)	C24—C25—H25	119.7
N1—P2—C41	105.52 (7)	C25—C26—C21	120.67 (15)
C31—P2—C41	100.78 (7)	C25—C26—H26	119.7
N1—C1—C2	112.95 (13)	C21—C26—H26	119.7
N1—C1—H1A	109	C36—C31—C32	118.21 (15)
C2—C1—H1A	109	C36—C31—P2	123.55 (12)
N1—C1—H1B	109	C32—C31—P2	118.08 (12)
C2—C1—H1B	109	C33—C32—C31	120.61 (15)
H1A—C1—H1B	107.8	C33—C32—H32	119.7
C1—C2—H2A	109.5	C31—C32—H32	119.7
C1—C2—H2B	109.5	C32—C33—C34	120.51 (16)
H2A—C2—H2B	109.5	C32—C33—H33	119.7
C1—C2—H2C	109.5	C34—C33—H33	119.7
H2A—C2—H2C	109.5	C35—C34—C33	119.42 (16)
H2B—C2—H2C	109.5	C35—C34—H34	120.3
C12—C11—C16	118.04 (14)	C33—C34—H34	120.3
C12—C11—P1	117.34 (11)	C34—C35—C36	120.32 (15)
C16—C11—P1	124.63 (12)	C34—C35—H35	119.8
C11—C12—C13	121.46 (14)	C36—C35—H35	119.8
C11—C12—H12	119.3	C35—C36—C31	120.88 (15)
C13—C12—H12	119.3	C35—C36—H36	119.6
C14—C13—C12	119.74 (15)	C31—C36—H36	119.6
C14—C13—H13A	120.1	C42—C41—C46	118.76 (14)
C12—C13—H13A	120.1	C42—C41—P2	116.96 (12)
C13—C14—C15	119.70 (14)	C46—C41—P2	124.14 (12)
C13—C14—H14	120.2	C43—C42—C41	120.57 (15)
C15—C14—H14	120.2	C43—C42—H42	119.7
C14—C15—C16	120.56 (15)	C41—C42—H42	119.7
C14—C15—H15	119.7	C44—C43—C42	119.90 (15)
C16—C15—H15	119.7	C44—C43—H43	120.1
C15—C16—C11	120.48 (15)	C42—C43—H43	120.1
C15—C16—H16	119.8	C45—C44—C43	120.33 (14)
C11—C16—H16	119.8	C45—C44—H44	119.8
C26—C21—C22	117.87 (15)	C43—C44—H44	119.8
C26—C21—P1	122.22 (12)	C44—C45—C46	119.69 (15)
C22—C21—P1	119.53 (12)	C44—C45—H45	120.2
C23—C22—C21	121.29 (15)	C46—C45—H45	120.2
C23—C22—H22	119.4	C45—C46—C41	120.75 (14)
C21—C22—H22	119.4	C45—C46—H46	119.6
C22—C23—C24	120.15 (15)	C41—C46—H46	119.6
C22—C23—H23	119.9
C1—N1—P1—C21	−53.54 (12)	C22—C23—C24—C25	−1.4 (2)
P2—N1—P1—C21	123.41 (9)	C23—C24—C25—C26	−0.1 (2)
C1—N1—P1—C11	50.91 (13)	C24—C25—C26—C21	1.6 (2)
P2—N1—P1—C11	−132.13 (9)	C22—C21—C26—C25	−1.6 (2)
C1—N1—P2—C31	−116.42 (11)	P1—C21—C26—C25	−174.42 (11)
P1—N1—P2—C31	66.40 (10)	N1—P2—C31—C36	14.23 (15)
C1—N1—P2—C41	137.38 (10)	C41—P2—C31—C36	123.86 (13)
P1—N1—P2—C41	−39.80 (11)	N1—P2—C31—C32	−170.32 (12)
P1—N1—C1—C2	−111.26 (14)	C41—P2—C31—C32	−60.70 (13)
P2—N1—C1—C2	71.52 (15)	C36—C31—C32—C33	−2.5 (2)
N1—P1—C11—C12	109.42 (13)	P2—C31—C32—C33	−178.19 (13)
C21—P1—C11—C12	−144.47 (12)	C31—C32—C33—C34	1.4 (3)
N1—P1—C11—C16	−70.44 (15)	C32—C33—C34—C35	0.3 (3)
C21—P1—C11—C16	35.67 (15)	C33—C34—C35—C36	−0.8 (3)
C16—C11—C12—C13	1.3 (2)	C34—C35—C36—C31	−0.3 (2)
P1—C11—C12—C13	−178.59 (12)	C32—C31—C36—C35	1.9 (2)
C11—C12—C13—C14	0.3 (2)	P2—C31—C36—C35	177.36 (12)
C12—C13—C14—C15	−1.2 (2)	N1—P2—C41—C42	−93.59 (13)
C13—C14—C15—C16	0.6 (2)	C31—P2—C41—C42	156.74 (12)
C14—C15—C16—C11	1.0 (2)	N1—P2—C41—C46	90.85 (14)
C12—C11—C16—C15	−1.9 (2)	C31—P2—C41—C46	−18.82 (14)
P1—C11—C16—C15	177.98 (12)	C46—C41—C42—C43	0.4 (2)
N1—P1—C21—C26	−32.09 (13)	P2—C41—C42—C43	−175.41 (12)
C11—P1—C21—C26	−139.97 (12)	C41—C42—C43—C44	0.1 (2)
N1—P1—C21—C22	155.21 (11)	C42—C43—C44—C45	−0.5 (2)
C11—P1—C21—C22	47.33 (13)	C43—C44—C45—C46	0.3 (2)
C26—C21—C22—C23	0.2 (2)	C44—C45—C46—C41	0.3 (2)
P1—C21—C22—C23	173.18 (11)	C42—C41—C46—C45	−0.6 (2)
C21—C22—C23—C24	1.3 (2)	P2—C41—C46—C45	174.89 (12)