N,N-Bis(diphenyl-phosphino)-1,2-dimethyl-propyl-amine.

The diphenyl-phosphine groups in the title compound, C(29)H(31)NP(2), are staggered relative to the PNP backbone. The N atom adopts an almost planar geometry with the two P atoms and the C atom attached to it, in order to accommodate the steric bulk of the phenyl groups and the alkyl group. Three C atoms of the 1,2-dimethylpropylamine group are disordered over two positions in a 9:1 ratio. The mol-ecules pack diagonally in the unit cell across the ac plane in a head-to-tail fashion.

Related literature

For similar structures, see: Keat et al. (1981 ▶); Cotton et al. (1996 ▶); Fei et al. (2003 ▶). For ethyl­ene tetra­merization, see: Bollmann et al. (2004 ▶).

Experimental

Crystal data

C29H31NP2

M = 455.49

Triclinic,

a = 9.242 (5) Å

b = 10.454 (5) Å

c = 12.899 (5) Å

α = 91.031 (5)°

β = 98.188 (5)°

γ = 102.775 (5)°

V = 1201.4 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 101 (2) K

0.47 × 0.29 × 0.14 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.912, T max = 0.974

24124 measured reflections

5947 independent reflections

5313 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.09

5947 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808001839/pv2057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001839/pv2057Isup2.hkl

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

C29H31NP2	Z = 2
Mr = 455.49	F000 = 484
Triclinic, P1	Dx = 1.259 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71069 Å
a = 9.242 (5) Å	Cell parameters from 5808 reflections
b = 10.454 (5) Å	θ = 2.5–28.3º
c = 12.899 (5) Å	µ = 0.20 mm−1
α = 91.031 (5)º	T = 101 (2) K
β = 98.188 (5)º	Needle, colourless
γ = 102.775 (5)º	0.47 × 0.29 × 0.14 mm
V = 1201.4 (10) Å3

Bruker X8 APEXII 4K Kappa CCD diffractometer	Rint = 0.031
ω and φ scans	θmax = 28.3º
Absorption correction: multi-scan(SADABS; Bruker, 2004)	θmin = 1.6º
Tmin = 0.913, Tmax = 0.974	h = −12→12
24124 measured reflections	k = −13→13
5947 independent reflections	l = −17→17
5313 reflections with I > 2σ(I)

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.8476P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.040	(Δ/σ)max = 0.001
wR(F2) = 0.108	Δρmax = 0.56 e Å−3
S = 1.09	Δρmin = −0.52 e Å−3
5947 reflections	Extinction correction: none
299 parameters

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 20 s/frame. A total of 1264 frames were collected with a frame width of 0.5° covering up to θ = 28.27° with 99.7% completeness accomplished.

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	Occ. (<1)
P1	0.70056 (4)	0.12612 (3)	0.21511 (3)	0.01317 (9)
P2	0.67790 (4)	0.37407 (4)	0.31828 (3)	0.01449 (9)
N1	0.78800 (13)	0.27976 (12)	0.27060 (10)	0.0140 (2)
C1	0.93360 (17)	0.35565 (16)	0.23925 (13)	0.0135 (3)	0.880 (3)
H1	0.9915	0.2902	0.2213	0.016*	0.880 (3)
C2	1.03165 (18)	0.44779 (17)	0.33011 (13)	0.0161 (3)	0.880 (3)
H2	0.9765	0.5164	0.3455	0.019*	0.880 (3)
C3	1.1814 (3)	0.5179 (2)	0.29853 (17)	0.0221 (5)	0.880 (3)
H3A	1.1627	0.5635	0.234	0.033*	0.880 (3)
H3B	1.2405	0.4534	0.2867	0.033*	0.880 (3)
H3C	1.237	0.5818	0.3547	0.033*	0.880 (3)
C4	1.0608 (2)	0.37797 (18)	0.42997 (13)	0.0276 (4)
H4A	0.9649	0.3331	0.4503	0.041*	0.880 (3)
H4B	1.1163	0.4422	0.486	0.041*	0.880 (3)
H4C	1.1199	0.3134	0.4183	0.041*	0.880 (3)
C5	0.90750 (18)	0.43599 (16)	0.14037 (13)	0.0222 (3)
H5A	0.8456	0.3773	0.0829	0.033*	0.880 (3)
H5B	1.0044	0.4764	0.1193	0.033*	0.880 (3)
H5C	0.8562	0.5047	0.1568	0.033*	0.880 (3)
C1'	0.9525 (13)	0.3419 (12)	0.3000 (11)	0.0135 (3)	0.120 (3)
H1'	1.0041	0.2825	0.2648	0.016*	0.120 (3)
C2'	0.9878 (13)	0.4706 (12)	0.2442 (10)	0.0161 (3)	0.120 (3)
H2'	0.9385	0.5336	0.2773	0.019*	0.120 (3)
C3'	1.164 (2)	0.530 (2)	0.2663 (15)	0.0221 (5)	0.120 (3)
H3'1	1.1961	0.5462	0.342	0.033*	0.120 (3)
H3'2	1.1869	0.6134	0.2315	0.033*	0.120 (3)
H3'3	1.2161	0.4683	0.239	0.033*	0.120 (3)
H4'1	1.044	0.2992	0.4706	0.041*	0.120 (3)
H4'2	1.0292	0.4487	0.4653	0.041*	0.120 (3)
H4'3	1.1677	0.4056	0.4242	0.041*	0.120 (3)
H5'1	0.9224	0.5132	0.0978	0.033*	0.120 (3)
H5'2	0.8003	0.4047	0.1438	0.033*	0.120 (3)
H5'3	0.945	0.3663	0.1085	0.033*	0.120 (3)
C11	0.72299 (16)	0.13544 (14)	0.07574 (11)	0.0160 (3)
C12	0.84843 (17)	0.11312 (15)	0.03598 (12)	0.0193 (3)
H12A	0.9257	0.0869	0.0815	0.023*
C13	0.86207 (19)	0.12861 (16)	−0.06911 (13)	0.0229 (3)
H13	0.9481	0.1128	−0.095	0.027*
C14	0.7501 (2)	0.16710 (17)	−0.13625 (13)	0.0259 (3)
H14	0.7596	0.1784	−0.2081	0.031*
C15	0.6245 (2)	0.18891 (19)	−0.09798 (13)	0.0273 (4)
H15A	0.5479	0.2155	−0.1438	0.033*
C16	0.60969 (18)	0.17224 (17)	0.00689 (13)	0.0221 (3)
H16	0.5222	0.1859	0.032	0.027*
C21	0.82593 (16)	0.01717 (14)	0.25649 (12)	0.0160 (3)
C22	0.78897 (18)	−0.10914 (15)	0.20857 (14)	0.0219 (3)
H22	0.7106	−0.1304	0.1506	0.026*
C23	0.8651 (2)	−0.20396 (16)	0.24445 (15)	0.0280 (4)
H23A	0.8368	−0.29	0.2121	0.034*
C24	0.9823 (2)	−0.17373 (18)	0.32730 (14)	0.0301 (4)
H24A	1.0354	−0.2382	0.3515	0.036*
C25	1.0208 (2)	−0.0491 (2)	0.37406 (14)	0.0335 (4)
H25A	1.1018	−0.0272	0.4303	0.04*
C26	0.9421 (2)	0.04519 (17)	0.33964 (13)	0.0251 (3)
H26	0.9687	0.1301	0.3739	0.03*
C31	0.50526 (16)	0.34906 (15)	0.22286 (11)	0.0160 (3)
C32	0.49159 (18)	0.44964 (17)	0.15521 (13)	0.0223 (3)
H32	0.5688	0.5275	0.1613	0.027*
C33	0.3657 (2)	0.4373 (2)	0.07870 (13)	0.0296 (4)
H33	0.3575	0.5064	0.033	0.035*
C34	0.2534 (2)	0.3248 (2)	0.06951 (14)	0.0312 (4)
H34	0.1684	0.3157	0.0167	0.037*
C35	0.26411 (18)	0.22487 (18)	0.13728 (15)	0.0283 (4)
H35	0.186	0.1477	0.1311	0.034*
C36	0.38839 (17)	0.23698 (16)	0.21414 (13)	0.0208 (3)
H36	0.3941	0.1687	0.2611	0.025*
C41	0.60386 (16)	0.28426 (15)	0.42658 (12)	0.0172 (3)
C42	0.48788 (18)	0.32576 (18)	0.46699 (13)	0.0245 (3)
H42	0.4469	0.3932	0.4343	0.029*
C43	0.43217 (19)	0.2696 (2)	0.55412 (14)	0.0293 (4)
H43	0.3531	0.2983	0.5804	0.035*
C44	0.49202 (19)	0.17178 (18)	0.60269 (13)	0.0272 (4)
H44	0.4542	0.1332	0.6623	0.033*
C45	0.60676 (19)	0.13068 (17)	0.56409 (13)	0.0245 (3)
H45	0.6477	0.0636	0.5975	0.029*
C46	0.66313 (17)	0.18625 (15)	0.47688 (12)	0.0195 (3)
H46	0.7426	0.1572	0.4514	0.023*

	U11	U22	U33	U12	U13	U23
P1	0.01201 (17)	0.01326 (17)	0.01526 (18)	0.00541 (13)	0.00153 (13)	0.00045 (13)
P2	0.01198 (17)	0.01493 (18)	0.01806 (19)	0.00708 (13)	0.00105 (13)	−0.00021 (14)
N1	0.0110 (5)	0.0127 (5)	0.0190 (6)	0.0053 (4)	0.0011 (4)	−0.0007 (4)
C1	0.0109 (7)	0.0155 (7)	0.0148 (8)	0.0050 (5)	0.0015 (6)	−0.0005 (6)
C2	0.0141 (7)	0.0184 (8)	0.0165 (7)	0.0057 (6)	0.0015 (6)	−0.0021 (6)
C3	0.0164 (9)	0.0249 (10)	0.0232 (12)	0.0010 (7)	0.0034 (9)	−0.0015 (9)
C4	0.0360 (9)	0.0294 (9)	0.0188 (8)	0.0104 (7)	0.0042 (7)	0.0024 (7)
C5	0.0250 (8)	0.0243 (8)	0.0195 (7)	0.0126 (6)	−0.0003 (6)	−0.0008 (6)
N1'	0.0110 (5)	0.0127 (5)	0.0190 (6)	0.0053 (4)	0.0011 (4)	−0.0007 (4)
C1'	0.0109 (7)	0.0155 (7)	0.0148 (8)	0.0050 (5)	0.0015 (6)	−0.0005 (6)
C2'	0.0141 (7)	0.0184 (8)	0.0165 (7)	0.0057 (6)	0.0015 (6)	−0.0021 (6)
C3'	0.0164 (9)	0.0249 (10)	0.0232 (12)	0.0010 (7)	0.0034 (9)	−0.0015 (9)
C4'	0.0360 (9)	0.0294 (9)	0.0188 (8)	0.0104 (7)	0.0042 (7)	0.0024 (7)
C5'	0.0250 (8)	0.0243 (8)	0.0195 (7)	0.0126 (6)	−0.0003 (6)	−0.0008 (6)
C11	0.0162 (6)	0.0164 (7)	0.0159 (7)	0.0055 (5)	0.0015 (5)	−0.0002 (5)
C12	0.0185 (7)	0.0209 (7)	0.0211 (7)	0.0091 (6)	0.0041 (6)	0.0022 (6)
C13	0.0257 (8)	0.0245 (8)	0.0226 (8)	0.0104 (6)	0.0095 (6)	0.0020 (6)
C14	0.0325 (9)	0.0303 (9)	0.0172 (7)	0.0104 (7)	0.0061 (6)	0.0011 (6)
C15	0.0271 (8)	0.0380 (10)	0.0187 (8)	0.0144 (7)	−0.0012 (6)	0.0025 (7)
C16	0.0191 (7)	0.0303 (8)	0.0194 (7)	0.0118 (6)	0.0016 (6)	0.0006 (6)
C21	0.0174 (7)	0.0163 (7)	0.0173 (7)	0.0083 (5)	0.0054 (5)	0.0031 (5)
C22	0.0210 (7)	0.0176 (7)	0.0292 (8)	0.0071 (6)	0.0057 (6)	0.0004 (6)
C23	0.0345 (9)	0.0163 (7)	0.0393 (10)	0.0120 (7)	0.0151 (8)	0.0033 (7)
C24	0.0442 (10)	0.0321 (9)	0.0264 (9)	0.0288 (8)	0.0142 (8)	0.0127 (7)
C25	0.0425 (10)	0.0436 (11)	0.0218 (8)	0.0308 (9)	−0.0036 (7)	0.0015 (8)
C26	0.0323 (9)	0.0265 (8)	0.0197 (8)	0.0184 (7)	−0.0038 (6)	−0.0028 (6)
C31	0.0135 (6)	0.0217 (7)	0.0159 (7)	0.0102 (5)	0.0027 (5)	0.0001 (5)
C32	0.0197 (7)	0.0300 (8)	0.0217 (8)	0.0126 (6)	0.0063 (6)	0.0076 (6)
C33	0.0283 (9)	0.0485 (11)	0.0194 (8)	0.0233 (8)	0.0044 (7)	0.0101 (7)
C34	0.0235 (8)	0.0522 (11)	0.0216 (8)	0.0226 (8)	−0.0056 (6)	−0.0080 (8)
C35	0.0164 (7)	0.0313 (9)	0.0365 (10)	0.0100 (6)	−0.0037 (7)	−0.0117 (7)
C36	0.0166 (7)	0.0211 (7)	0.0267 (8)	0.0099 (6)	0.0017 (6)	−0.0015 (6)
C41	0.0163 (7)	0.0205 (7)	0.0149 (7)	0.0062 (5)	−0.0004 (5)	−0.0009 (5)
C42	0.0221 (8)	0.0346 (9)	0.0207 (8)	0.0148 (7)	0.0033 (6)	0.0016 (7)
C43	0.0228 (8)	0.0457 (11)	0.0222 (8)	0.0122 (7)	0.0062 (6)	0.0001 (7)
C44	0.0273 (8)	0.0352 (9)	0.0162 (7)	0.0009 (7)	0.0038 (6)	0.0009 (7)
C45	0.0299 (8)	0.0243 (8)	0.0178 (7)	0.0059 (6)	−0.0010 (6)	0.0018 (6)
C46	0.0210 (7)	0.0208 (7)	0.0173 (7)	0.0077 (6)	0.0000 (6)	−0.0009 (6)

P1—N1	1.7219 (14)	C15—C16	1.389 (2)
P1—C21	1.8314 (16)	C15—H15A	0.95
P1—C11	1.8406 (17)	C16—H16	0.95
P2—N1	1.7279 (13)	C21—C26	1.382 (2)
P2—C41	1.8267 (17)	C21—C22	1.398 (2)
P2—C31	1.8367 (16)	C22—C23	1.387 (2)
N1—C1	1.516 (2)	C22—H22	0.95
C1—C2	1.547 (2)	C23—C24	1.386 (3)
C1—C5	1.559 (2)	C23—H23A	0.95
C1—H1	1.00	C24—C25	1.376 (3)
C2—C4	1.512 (2)	C24—H24A	0.95
C2—C3	1.531 (3)	C25—C26	1.392 (2)
C2—H2	1.00	C25—H25A	0.95
C3—H3A	0.98	C26—H26	0.95
C3—H3B	0.98	C31—C32	1.394 (2)
C3—H3C	0.98	C31—C36	1.398 (2)
C4—H4A	0.98	C32—C33	1.395 (2)
C4—H4B	0.98	C32—H32	0.95
C4—H4C	0.98	C33—C34	1.376 (3)
C5—H5A	0.98	C33—H33	0.95
C5—H5B	0.98	C34—C35	1.385 (3)
C5—H5C	0.98	C34—H34	0.95
C1'—C2'	1.531 (18)	C35—C36	1.387 (2)
C1'—H1'	1.00	C35—H35	0.95
C2'—C3'	1.59 (2)	C36—H36	0.95
C2'—H2'	1.00	C41—C46	1.393 (2)
C3'—H3'1	0.98	C41—C42	1.402 (2)
C3'—H3'2	0.98	C42—C43	1.388 (2)
C3'—H3'3	0.98	C42—H42	0.95
C11—C12	1.395 (2)	C43—C44	1.386 (3)
C11—C16	1.400 (2)	C43—H43	0.95
C12—C13	1.388 (2)	C44—C45	1.379 (3)
C12—H12A	0.95	C44—H44	0.95
C13—C14	1.387 (2)	C45—C46	1.390 (2)
C13—H13	0.95	C45—H45	0.95
C14—C15	1.386 (2)	C46—H46	0.95
C14—H14	0.95
N1—P1—C21	106.57 (7)	C14—C15—C16	120.55 (15)
N1—P1—C11	104.94 (7)	C14—C15—H15A	119.7
C21—P1—C11	99.56 (7)	C16—C15—H15A	119.7
N1—P2—C41	104.98 (7)	C15—C16—C11	120.32 (15)
N1—P2—C31	106.17 (7)	C15—C16—H16	119.8
C41—P2—C31	99.78 (7)	C11—C16—H16	119.8
C1—N1—P1	121.49 (10)	C26—C21—C22	117.95 (14)
C1—N1—P2	115.52 (10)	C26—C21—P1	124.64 (12)
P1—N1—P2	117.83 (7)	C22—C21—P1	116.91 (12)
N1—C1—C2	112.09 (13)	C23—C22—C21	120.96 (16)
N1—C1—C5	112.51 (12)	C23—C22—H22	119.5
C2—C1—C5	109.68 (13)	C21—C22—H22	119.5
N1—C1—H1	107.4	C24—C23—C22	120.29 (16)
C2—C1—H1	107.4	C24—C23—H23A	119.9
C5—C1—H1	107.4	C22—C23—H23A	119.9
C4—C2—C3	109.39 (15)	C25—C24—C23	119.14 (15)
C4—C2—C1	113.19 (14)	C25—C24—H24A	120.4
C3—C2—C1	111.16 (15)	C23—C24—H24A	120.4
C4—C2—H2	107.6	C24—C25—C26	120.57 (17)
C3—C2—H2	107.6	C24—C25—H25A	119.7
C1—C2—H2	107.6	C26—C25—H25A	119.7
C2—C3—H3A	109.5	C21—C26—C25	121.07 (16)
C2—C3—H3B	109.5	C21—C26—H26	119.5
H3A—C3—H3B	109.5	C25—C26—H26	119.5
C2—C3—H3C	109.5	C32—C31—C36	118.56 (14)
H3A—C3—H3C	109.5	C32—C31—P2	117.02 (12)
H3B—C3—H3C	109.5	C36—C31—P2	124.42 (12)
C2—C4—H4A	109.5	C31—C32—C33	120.72 (16)
C2—C4—H4B	109.5	C31—C32—H32	119.6
H4A—C4—H4B	109.5	C33—C32—H32	119.6
C2—C4—H4C	109.5	C34—C33—C32	119.92 (17)
H4A—C4—H4C	109.5	C34—C33—H33	120
H4B—C4—H4C	109.5	C32—C33—H33	120
C1—C5—H5A	109.5	C33—C34—C35	120.06 (16)
C1—C5—H5B	109.5	C33—C34—H34	120
H5A—C5—H5B	109.5	C35—C34—H34	120
C1—C5—H5C	109.5	C34—C35—C36	120.32 (17)
H5A—C5—H5C	109.5	C34—C35—H35	119.8
H5B—C5—H5C	109.5	C36—C35—H35	119.8
C2'—C1'—H1'	104.3	C35—C36—C31	120.38 (16)
C1'—C2'—C3'	109.0 (11)	C35—C36—H36	119.8
C1'—C2'—H2'	107.2	C31—C36—H36	119.8
C3'—C2'—H2'	107.2	C46—C41—C42	118.29 (15)
C2'—C3'—H3'1	109.5	C46—C41—P2	124.54 (12)
C2'—C3'—H3'2	109.5	C42—C41—P2	116.92 (12)
H3'1—C3'—H3'2	109.5	C43—C42—C41	120.92 (16)
C2'—C3'—H3'3	109.5	C43—C42—H42	119.5
H3'1—C3'—H3'3	109.5	C41—C42—H42	119.5
H3'2—C3'—H3'3	109.5	C44—C43—C42	119.92 (16)
C12—C11—C16	118.48 (14)	C44—C43—H43	120
C12—C11—P1	123.86 (11)	C42—C43—H43	120
C16—C11—P1	117.61 (11)	C45—C44—C43	119.71 (16)
C13—C12—C11	121.00 (14)	C45—C44—H44	120.1
C13—C12—H12A	119.5	C43—C44—H44	120.1
C11—C12—H12A	119.5	C44—C45—C46	120.75 (16)
C14—C13—C12	120.00 (15)	C44—C45—H45	119.6
C14—C13—H13	120	C46—C45—H45	119.6
C12—C13—H13	120	C45—C46—C41	120.40 (15)
C15—C14—C13	119.63 (15)	C45—C46—H46	119.8
C15—C14—H14	120.2	C41—C46—H46	119.8
C13—C14—H14	120.2