N,N-Bis(diphenyl-phosphan-yl)benzyl-amine.

In the title compound, C(31)H(27)NP(2), the diphenyl-phosphanyl groups are staggered relative to the PNP backbone. The N atom is displaced by 0.219 (2) Å from the plane formed by the two P atoms and the methylene C atom. The angles around the N atom are 120.84 (16), 113.29 (16) and 120.57 (12)°, indicating that it exhibits a distorted trigonal-pyramidal geometry. There are no classical inter-molecular inter-actions.

Related literature

For a related structure, see: Cloete et al. (2008 ▶).

Experimental

Crystal data

C31H27NP2

M = 475.48

Triclinic,

a = 10.381 (2) Å

b = 10.455 (2) Å

c = 13.239 (3) Å

α = 69.71 (3)°

β = 79.24 (3)°

γ = 70.21 (3)°

V = 1264.2 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.24 × 0.20 × 0.16 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.955, T max = 0.970

11566 measured reflections

4453 independent reflections

3496 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.173

S = 1.04

4453 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.92 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000997/pv2373sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000997/pv2373Isup2.hkl

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

C31H27NP2	Z = 2
Mr = 475.48	F(000) = 500
Triclinic, P1	Dx = 1.249 Mg m−3
a = 10.381 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.455 (2) Å	Cell parameters from 3212 reflections
c = 13.239 (3) Å	θ = 2.1–27.9°
α = 69.71 (3)°	µ = 0.19 mm−1
β = 79.24 (3)°	T = 293 K
γ = 70.21 (3)°	Block, colourless
V = 1264.2 (4) Å3	0.24 × 0.20 × 0.16 mm

Rigaku Saturn diffractometer	4453 independent reflections
Radiation source: rotating anode	3496 reflections with I > 2σ(I)
confocal	Rint = 0.040
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −12→12
Tmin = 0.955, Tmax = 0.970	k = −12→12
11566 measured reflections	l = −13→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H-atom parameters constrained
wR(F2) = 0.173	w = 1/[σ2(Fo2) + (0.1075P)2 + 0.1112P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.002
4453 reflections	Δρmax = 0.92 e Å−3
308 parameters	Δρmin = −0.34 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.077 (9)

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.

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 > σ(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
P1	0.09360 (6)	0.38539 (7)	0.11067 (5)	0.0374 (3)
P2	0.26571 (7)	0.18718 (7)	0.29471 (5)	0.0419 (3)
N1	0.1113 (2)	0.2572 (2)	0.23768 (15)	0.0370 (5)
C1	0.2180 (2)	0.2936 (3)	0.02258 (19)	0.0387 (6)
C2	0.2562 (3)	0.1463 (3)	0.0436 (2)	0.0482 (7)
H2	0.2294	0.0896	0.1102	0.058*
C3	0.3332 (3)	0.0827 (3)	−0.0330 (3)	0.0605 (8)
H3	0.3582	−0.0159	−0.0176	0.073*
C4	0.3727 (3)	0.1664 (4)	−0.1321 (3)	0.0649 (9)
H4	0.4227	0.1244	−0.1845	0.078*
C5	0.3384 (3)	0.3109 (4)	−0.1535 (2)	0.0555 (8)
H5	0.3670	0.3666	−0.2199	0.067*
C6	0.2620 (3)	0.3749 (3)	−0.0775 (2)	0.0466 (7)
H6	0.2394	0.4734	−0.0932	0.056*
C7	0.1735 (3)	0.5146 (3)	0.11555 (19)	0.0414 (6)
C8	0.0838 (3)	0.6401 (3)	0.1334 (2)	0.0537 (7)
H8	−0.0106	0.6565	0.1375	0.064*
C9	0.1351 (4)	0.7407 (4)	0.1451 (3)	0.0715 (10)
H9	0.0756	0.8239	0.1577	0.086*
C10	0.2756 (4)	0.7153 (4)	0.1378 (3)	0.0735 (10)
H10	0.3102	0.7815	0.1470	0.088*
C11	0.3646 (4)	0.5951 (4)	0.1174 (2)	0.0664 (9)
H11	0.4588	0.5808	0.1110	0.080*
C12	0.3139 (3)	0.4948 (3)	0.1061 (2)	0.0501 (7)
H12	0.3747	0.4130	0.0921	0.060*
C13	0.2223 (3)	0.2333 (3)	0.4218 (2)	0.0432 (6)
C14	0.2042 (3)	0.3744 (3)	0.4148 (2)	0.0550 (8)
H14	0.2155	0.4404	0.3479	0.066*
C15	0.1697 (4)	0.4166 (4)	0.5069 (3)	0.0643 (9)
H15	0.1543	0.5118	0.5009	0.077*
C16	0.1577 (3)	0.3205 (4)	0.6068 (3)	0.0627 (8)
H16	0.1366	0.3498	0.6682	0.075*
C17	0.1771 (4)	0.1816 (4)	0.6155 (2)	0.0682 (9)
H17	0.1697	0.1157	0.6832	0.082*
C18	0.2077 (3)	0.1378 (3)	0.5233 (2)	0.0590 (8)
H18	0.2186	0.0432	0.5301	0.071*
C19	0.2901 (3)	−0.0053 (3)	0.3464 (2)	0.0465 (7)
C20	0.4192 (3)	−0.0896 (4)	0.3840 (2)	0.0628 (8)
H20	0.4828	−0.0462	0.3865	0.075*
C21	0.4526 (4)	−0.2377 (4)	0.4176 (3)	0.0760 (11)
H21	0.5387	−0.2934	0.4417	0.091*
C22	0.3580 (4)	−0.3011 (4)	0.4150 (3)	0.0749 (10)
H22	0.3802	−0.4001	0.4371	0.090*
C23	0.2312 (5)	−0.2198 (4)	0.3803 (3)	0.0780 (11)
H23	0.1671	−0.2637	0.3797	0.094*
C24	0.1982 (4)	−0.0737 (3)	0.3462 (3)	0.0627 (9)
H24	0.1116	−0.0197	0.3224	0.075*
C25	−0.0189 (3)	0.2644 (3)	0.3057 (2)	0.0476 (7)
H25A	−0.0543	0.3578	0.3162	0.057*
H25B	0.0001	0.1942	0.3760	0.057*
C26	−0.1304 (3)	0.2389 (3)	0.2617 (2)	0.0412 (6)
C27	−0.2631 (3)	0.2773 (4)	0.3079 (2)	0.0592 (8)
H27	−0.2814	0.3202	0.3621	0.071*
C28	−0.3695 (3)	0.2528 (4)	0.2748 (3)	0.0748 (10)
H28	−0.4579	0.2781	0.3073	0.090*
C29	−0.3446 (3)	0.1919 (4)	0.1947 (3)	0.0709 (10)
H29	−0.4161	0.1771	0.1715	0.085*
C30	−0.2131 (3)	0.1522 (3)	0.1481 (3)	0.0625 (8)
H30	−0.1956	0.1098	0.0938	0.075*
C31	−0.1065 (3)	0.1754 (3)	0.1822 (2)	0.0517 (7)
H31	−0.0178	0.1475	0.1508	0.062*

	U11	U22	U33	U12	U13	U23
P1	0.0321 (4)	0.0439 (4)	0.0347 (4)	−0.0143 (3)	−0.0039 (3)	−0.0067 (3)
P2	0.0344 (4)	0.0498 (5)	0.0387 (4)	−0.0170 (3)	−0.0062 (3)	−0.0041 (3)
N1	0.0289 (10)	0.0492 (12)	0.0313 (11)	−0.0153 (9)	−0.0036 (8)	−0.0062 (9)
C1	0.0328 (13)	0.0487 (15)	0.0362 (14)	−0.0164 (11)	−0.0069 (10)	−0.0085 (12)
C2	0.0483 (16)	0.0526 (17)	0.0466 (16)	−0.0200 (13)	−0.0008 (13)	−0.0153 (13)
C3	0.061 (2)	0.0558 (18)	0.067 (2)	−0.0139 (15)	0.0009 (16)	−0.0282 (16)
C4	0.060 (2)	0.086 (2)	0.057 (2)	−0.0253 (18)	0.0100 (15)	−0.0365 (19)
C5	0.0526 (18)	0.074 (2)	0.0428 (17)	−0.0286 (15)	0.0044 (13)	−0.0161 (15)
C6	0.0404 (15)	0.0565 (17)	0.0413 (15)	−0.0193 (13)	−0.0038 (12)	−0.0080 (13)
C7	0.0451 (15)	0.0462 (15)	0.0332 (14)	−0.0199 (12)	−0.0020 (11)	−0.0072 (11)
C8	0.0608 (19)	0.0570 (18)	0.0441 (17)	−0.0183 (15)	−0.0058 (13)	−0.0146 (14)
C9	0.097 (3)	0.061 (2)	0.064 (2)	−0.0296 (19)	−0.0015 (19)	−0.0260 (17)
C10	0.105 (3)	0.075 (2)	0.061 (2)	−0.058 (2)	−0.004 (2)	−0.0172 (18)
C11	0.073 (2)	0.087 (2)	0.056 (2)	−0.051 (2)	−0.0017 (16)	−0.0172 (18)
C12	0.0466 (16)	0.0574 (17)	0.0483 (17)	−0.0249 (13)	−0.0024 (12)	−0.0102 (14)
C13	0.0388 (14)	0.0521 (16)	0.0376 (15)	−0.0189 (12)	−0.0091 (11)	−0.0040 (12)
C14	0.0646 (19)	0.0534 (18)	0.0467 (17)	−0.0223 (15)	−0.0119 (14)	−0.0064 (14)
C15	0.074 (2)	0.062 (2)	0.061 (2)	−0.0209 (17)	−0.0122 (17)	−0.0199 (17)
C16	0.067 (2)	0.075 (2)	0.0497 (19)	−0.0218 (17)	−0.0025 (15)	−0.0231 (17)
C17	0.083 (2)	0.069 (2)	0.0392 (18)	−0.0206 (18)	−0.0024 (16)	−0.0033 (16)
C18	0.073 (2)	0.0525 (17)	0.0500 (18)	−0.0209 (16)	−0.0067 (15)	−0.0102 (14)
C19	0.0424 (15)	0.0517 (16)	0.0385 (15)	−0.0087 (12)	−0.0050 (11)	−0.0099 (12)
C20	0.0447 (17)	0.067 (2)	0.062 (2)	−0.0108 (15)	0.0009 (14)	−0.0100 (16)
C21	0.061 (2)	0.065 (2)	0.059 (2)	0.0112 (18)	0.0028 (16)	−0.0004 (17)
C22	0.097 (3)	0.0476 (19)	0.067 (2)	−0.011 (2)	−0.003 (2)	−0.0126 (17)
C23	0.111 (3)	0.053 (2)	0.070 (2)	−0.030 (2)	−0.029 (2)	−0.0017 (17)
C24	0.071 (2)	0.0572 (19)	0.061 (2)	−0.0244 (16)	−0.0238 (16)	−0.0046 (15)
C25	0.0382 (15)	0.0668 (18)	0.0390 (15)	−0.0245 (13)	0.0023 (11)	−0.0118 (13)
C26	0.0329 (13)	0.0480 (15)	0.0365 (14)	−0.0191 (11)	−0.0025 (11)	0.0013 (12)
C27	0.0410 (16)	0.079 (2)	0.0530 (18)	−0.0223 (15)	0.0004 (13)	−0.0127 (16)
C28	0.0345 (17)	0.099 (3)	0.084 (3)	−0.0276 (17)	−0.0026 (16)	−0.013 (2)
C29	0.0446 (18)	0.089 (2)	0.078 (2)	−0.0345 (17)	−0.0196 (16)	−0.002 (2)
C30	0.061 (2)	0.071 (2)	0.0600 (19)	−0.0345 (16)	−0.0180 (15)	−0.0041 (16)
C31	0.0431 (16)	0.0624 (18)	0.0503 (17)	−0.0241 (14)	−0.0059 (13)	−0.0087 (14)

P1—N1	1.744 (2)	C15—C16	1.369 (4)
P1—C1	1.823 (3)	C15—H15	0.9300
P1—C7	1.832 (3)	C16—C17	1.364 (5)
P2—N1	1.717 (2)	C16—H16	0.9300
P2—C19	1.829 (3)	C17—C18	1.393 (4)
P2—C13	1.843 (3)	C17—H17	0.9300
N1—C25	1.472 (3)	C18—H18	0.9300
C1—C2	1.392 (4)	C19—C24	1.374 (4)
C1—C6	1.394 (4)	C19—C20	1.402 (4)
C2—C3	1.382 (4)	C20—C21	1.390 (5)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.380 (5)	C21—C22	1.369 (5)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.366 (5)	C22—C23	1.365 (5)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.377 (4)	C23—C24	1.371 (4)
C5—H5	0.9300	C23—H23	0.9300
C6—H6	0.9300	C24—H24	0.9300
C7—C12	1.389 (4)	C25—C26	1.522 (3)
C7—C8	1.397 (4)	C25—H25A	0.9700
C8—C9	1.391 (4)	C25—H25B	0.9700
C8—H8	0.9300	C26—C31	1.374 (4)
C9—C10	1.383 (5)	C26—C27	1.384 (4)
C9—H9	0.9300	C27—C28	1.389 (4)
C10—C11	1.365 (5)	C27—H27	0.9300
C10—H10	0.9300	C28—C29	1.360 (5)
C11—C12	1.382 (4)	C28—H28	0.9300
C11—H11	0.9300	C29—C30	1.377 (5)
C12—H12	0.9300	C29—H29	0.9300
C13—C18	1.387 (4)	C30—C31	1.390 (4)
C13—C14	1.395 (4)	C30—H30	0.9300
C14—C15	1.383 (4)	C31—H31	0.9300
C14—H14	0.9300
N1—P1—C1	103.38 (11)	C14—C15—H15	119.5
N1—P1—C7	104.88 (11)	C17—C16—C15	119.5 (3)
C1—P1—C7	102.31 (12)	C17—C16—H16	120.2
N1—P2—C19	104.40 (12)	C15—C16—H16	120.2
N1—P2—C13	102.91 (11)	C16—C17—C18	120.3 (3)
C19—P2—C13	100.61 (12)	C16—C17—H17	119.9
C25—N1—P2	120.84 (16)	C18—C17—H17	119.9
C25—N1—P1	113.29 (16)	C13—C18—C17	120.9 (3)
P2—N1—P1	120.57 (12)	C13—C18—H18	119.6
C2—C1—C6	117.8 (2)	C17—C18—H18	119.6
C2—C1—P1	122.8 (2)	C24—C19—C20	117.9 (3)
C6—C1—P1	118.7 (2)	C24—C19—P2	126.5 (2)
C3—C2—C1	121.2 (3)	C20—C19—P2	115.5 (2)
C3—C2—H2	119.4	C21—C20—C19	120.4 (3)
C1—C2—H2	119.4	C21—C20—H20	119.8
C4—C3—C2	119.6 (3)	C19—C20—H20	119.8
C4—C3—H3	120.2	C22—C21—C20	119.6 (3)
C2—C3—H3	120.2	C22—C21—H21	120.2
C5—C4—C3	120.0 (3)	C20—C21—H21	120.2
C5—C4—H4	120.0	C23—C22—C21	120.4 (3)
C3—C4—H4	120.0	C23—C22—H22	119.8
C4—C5—C6	120.6 (3)	C21—C22—H22	119.8
C4—C5—H5	119.7	C22—C23—C24	120.2 (4)
C6—C5—H5	119.7	C22—C23—H23	119.9
C5—C6—C1	120.7 (3)	C24—C23—H23	119.9
C5—C6—H6	119.6	C23—C24—C19	121.5 (3)
C1—C6—H6	119.6	C23—C24—H24	119.3
C12—C7—C8	118.8 (3)	C19—C24—H24	119.3
C12—C7—P1	125.2 (2)	N1—C25—C26	115.6 (2)
C8—C7—P1	116.0 (2)	N1—C25—H25A	108.4
C9—C8—C7	120.2 (3)	C26—C25—H25A	108.4
C9—C8—H8	119.9	N1—C25—H25B	108.4
C7—C8—H8	119.9	C26—C25—H25B	108.4
C10—C9—C8	119.2 (3)	H25A—C25—H25B	107.4
C10—C9—H9	120.4	C31—C26—C27	118.1 (3)
C8—C9—H9	120.4	C31—C26—C25	124.1 (2)
C11—C10—C9	121.3 (3)	C27—C26—C25	117.7 (2)
C11—C10—H10	119.4	C26—C27—C28	121.0 (3)
C9—C10—H10	119.4	C26—C27—H27	119.5
C10—C11—C12	119.6 (3)	C28—C27—H27	119.5
C10—C11—H11	120.2	C29—C28—C27	120.1 (3)
C12—C11—H11	120.2	C29—C28—H28	119.9
C11—C12—C7	120.8 (3)	C27—C28—H28	119.9
C11—C12—H12	119.6	C28—C29—C30	119.7 (3)
C7—C12—H12	119.6	C28—C29—H29	120.1
C18—C13—C14	117.9 (3)	C30—C29—H29	120.1
C18—C13—P2	124.8 (2)	C29—C30—C31	120.1 (3)
C14—C13—P2	117.3 (2)	C29—C30—H30	120.0
C15—C14—C13	120.2 (3)	C31—C30—H30	120.0
C15—C14—H14	119.9	C26—C31—C30	120.9 (3)
C13—C14—H14	119.9	C26—C31—H31	119.6
C16—C15—C14	121.1 (3)	C30—C31—H31	119.6
C16—C15—H15	119.5
C19—P2—N1—C25	73.0 (2)	N1—P2—C13—C14	−76.3 (2)
C13—P2—N1—C25	−31.7 (2)	C19—P2—C13—C14	176.1 (2)
C19—P2—N1—P1	−134.41 (14)	C18—C13—C14—C15	−1.5 (4)
C13—P2—N1—P1	120.88 (14)	P2—C13—C14—C15	179.1 (2)
C1—P1—N1—C25	−145.17 (17)	C13—C14—C15—C16	2.5 (5)
C7—P1—N1—C25	107.98 (18)	C14—C15—C16—C17	−1.5 (5)
C1—P1—N1—P2	60.34 (15)	C15—C16—C17—C18	−0.5 (5)
C7—P1—N1—P2	−46.52 (16)	C14—C13—C18—C17	−0.5 (4)
N1—P1—C1—C2	28.8 (2)	P2—C13—C18—C17	178.9 (2)
C7—P1—C1—C2	137.6 (2)	C16—C17—C18—C13	1.5 (5)
N1—P1—C1—C6	−160.77 (19)	N1—P2—C19—C24	−4.7 (3)
C7—P1—C1—C6	−52.0 (2)	C13—P2—C19—C24	101.7 (3)
C6—C1—C2—C3	−1.1 (4)	N1—P2—C19—C20	171.5 (2)
P1—C1—C2—C3	169.4 (2)	C13—P2—C19—C20	−82.1 (2)
C1—C2—C3—C4	−0.3 (4)	C24—C19—C20—C21	1.3 (4)
C2—C3—C4—C5	1.5 (5)	P2—C19—C20—C21	−175.2 (2)
C3—C4—C5—C6	−1.3 (5)	C19—C20—C21—C22	−0.8 (5)
C4—C5—C6—C1	0.0 (4)	C20—C21—C22—C23	−0.3 (5)
C2—C1—C6—C5	1.2 (4)	C21—C22—C23—C24	0.9 (6)
P1—C1—C6—C5	−169.7 (2)	C22—C23—C24—C19	−0.3 (5)
N1—P1—C7—C12	77.6 (2)	C20—C19—C24—C23	−0.8 (5)
C1—P1—C7—C12	−30.0 (2)	P2—C19—C24—C23	175.3 (3)
N1—P1—C7—C8	−100.4 (2)	P2—N1—C25—C26	−143.99 (19)
C1—P1—C7—C8	152.0 (2)	P1—N1—C25—C26	61.6 (3)
C12—C7—C8—C9	−2.1 (4)	N1—C25—C26—C31	17.6 (4)
P1—C7—C8—C9	176.0 (2)	N1—C25—C26—C27	−164.9 (2)
C7—C8—C9—C10	0.6 (5)	C31—C26—C27—C28	−0.2 (4)
C8—C9—C10—C11	1.2 (5)	C25—C26—C27—C28	−177.8 (3)
C9—C10—C11—C12	−1.5 (5)	C26—C27—C28—C29	−0.9 (5)
C10—C11—C12—C7	−0.1 (5)	C27—C28—C29—C30	1.2 (5)
C8—C7—C12—C11	1.9 (4)	C28—C29—C30—C31	−0.5 (5)
P1—C7—C12—C11	−176.1 (2)	C27—C26—C31—C30	0.9 (4)
N1—P2—C13—C18	104.4 (3)	C25—C26—C31—C30	178.3 (3)
C19—P2—C13—C18	−3.2 (3)	C29—C30—C31—C26	−0.5 (4)