[2-(1H-Inden-3-yl)­ethyl]­di­phenyl­phos­phine–borane

Groux, L.F.; Zargarian, D.

doi:10.1107/S0108270100009690

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[2-(1H-Inden-3-yl)ethyl]diphenylphosphine-borane

L. F. Groux and D. Zargarian

The title compound, C₂₃H₂₄BP, crystallizes in the centrosymmetric space group P2₁/c, with one molecule in the asymmetric unit. The indene moiety is essentially planar. The P-B bond length is 1.923 (3) Å, which is within the expected range.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009690/qa0339sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009690/qa0339Isup2.hkl Contains datablock I

CCDC reference: 150404

Comment top

The title compound, (I), is a protected bidentate phosphinoindenyl ligand synthesized during the course of our studies on transition metal complexes bearing chelating indenyl ligands. We studied this compound in order to compare its strucural parameters with those found in complexes wherein the indenyl moiety is coordinated to a transition metal. The borane protects the phosphine against oxidation.

N-[2-(1H-Inden-3-yl)ethyl]-p-toluenesulfonamide (Gainsford & Lensink, 1996) and N-[3-(inden-3-yl)propyl]benzylammonium bromide (Groux et al., 1999) present virtually the same structural parameters.

Experimental top

IndH-(CH₂)₂PPh₂ was prepared following Kauffmann's procedure (Kauffmann et al., 1985). BH₃·THF (6.1 ml of a 1 M solution in THF, 6.1 mmol) was syringed onto a 60 ml solution of the ligand (1.33 g, 4.05 mmol) in THF and stirred for 1 h at room temperature. The reaction mixture containing a white precipitate was evaporated to dryness. The crude material was purified by flash chromatography (silica gel, 1:3 ethyl acetate/hexane). White crystals were obtained after recrystallization in ethyl acetate/hexane (1:1). The compound was characterized by NMR spectroscopy and elemental analysis. ³¹P {¹H} (CDCl₃): 16.6; ¹H (CDCl₃): 7.7, 7.5 and 7.2 (m, aromatic protons of indene and phenyls), 6.25 (s, H2), 3.29 (s, H3), 2.78 and 2.60 (m, –CH₂—CH₂–), 1.15 (br, BH₃); ¹³C {¹H} (CDCl₃): 144.5 and 143.6 (C3A and C7A), 132.3, 131.4, 129.4, 129.0, 128.6, 124.5, 118.9 (C2), 24.6 (d, CH₂P), 21.5 (Ind-CH₂). Anatysis calculated for C₂₃H₂₄BP: C 80.7, H 7.1%; found: C 80.6, H 7.3%.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: locally modified NRC-2, NRC-2A (Ahmed et al., 1973); program(s) used to solve structure: SHELXS93 (Sheldrick, 1990); program(s) used to refine structure: NRCVAX (Gabe et al., 1989) and SHELXL93 (Sheldrick, 1993; 1996 revision); software used to prepare material for publication: NRCVAX and SHELXL93.

[2-(1–3H-Indenyl)ethyl]-diphenylphosphineborane top

Crystal data top

C₂₃H₂₄BP	F(000) = 728
M_r = 342.20	D_x = 1.166 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54056 Å
a = 14.061 (5) Å	Cell parameters from 25 reflections
b = 6.644 (3) Å	θ = 20–23°
c = 21.018 (10) Å	µ = 1.23 mm⁻¹
β = 96.82 (3)°	T = 293 K
V = 1949.6 (15) Å³	Plate, white
Z = 4	0.88 × 0.12 × 0.02 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1679 reflections with I > 2σ(I)
Radiation source: normal-focus xray tube	R_int = 0.065
Graphite monochromator	θ_max = 69.8°, θ_min = 3.2°
ω/2θ scans	h = −17→17
Absorption correction: integration (ABSORP in NRCVAX; Gabe et al, 1989)	k = −8→8
T_min = 0.695, T_max = 0.978	l = −25→25
30965 measured reflections	5 standard reflections every 60 min
3689 independent reflections	intensity decay: no decay, variation 0.0%

Refinement top

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.0184P)²] where P = (F_o² + 2F_c²)/3
S = 0.64	(Δ/σ)_max = 0.001
3689 reflections	Δρ_max = 0.24 e Å⁻³
228 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL96 (Sheldrick, 1996), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00064 (6)

Crystal data top

C₂₃H₂₄BP	V = 1949.6 (15) Å³
M_r = 342.20	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 14.061 (5) Å	µ = 1.23 mm⁻¹
b = 6.644 (3) Å	T = 293 K
c = 21.018 (10) Å	0.88 × 0.12 × 0.02 mm
β = 96.82 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1679 reflections with I > 2σ(I)
Absorption correction: integration (ABSORP in NRCVAX; Gabe et al, 1989)	R_int = 0.065
T_min = 0.695, T_max = 0.978	5 standard reflections every 60 min
30965 measured reflections	intensity decay: no decay, variation 0.0%
3689 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 0.64	Δρ_max = 0.24 e Å⁻³
3689 reflections	Δρ_min = −0.20 e Å⁻³
228 parameters

Special details top

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. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating R-factor_obs 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
P	0.13829 (5)	0.25277 (12)	0.35401 (3)	0.03620 (17)
C1	0.29270 (17)	0.0324 (4)	0.21444 (11)	0.0370 (7)
C2	0.25599 (19)	−0.1417 (4)	0.19081 (12)	0.0513 (8)
H2	0.1970	−0.1934	0.1986	0.062*
C3	0.32279 (19)	−0.2424 (5)	0.15005 (13)	0.0590 (8)
H3A	0.3419	−0.3742	0.1669	0.071*
H3B	0.2932	−0.2568	0.1062	0.071*
C3A	0.40640 (19)	−0.1021 (4)	0.15402 (12)	0.0426 (7)
C4	0.4908 (2)	−0.1135 (5)	0.12724 (12)	0.0524 (8)
H4	0.5036	−0.2227	0.1019	0.063*
C5	0.5562 (2)	0.0407 (5)	0.13884 (13)	0.0605 (10)
H5	0.6138	0.0351	0.1212	0.073*
C6	0.5372 (2)	0.2041 (5)	0.17643 (13)	0.0586 (9)
H6	0.5819	0.3073	0.1835	0.070*
C7	0.45208 (17)	0.2149 (4)	0.20358 (12)	0.0464 (8)
H7	0.4396	0.3239	0.2291	0.056*
C7A	0.38650 (17)	0.0616 (4)	0.19207 (11)	0.0353 (7)
C8	0.25431 (16)	0.1731 (4)	0.25996 (11)	0.0413 (7)
H8A	0.2430	0.3022	0.2389	0.050*
H8B	0.3030	0.1930	0.2962	0.050*
C9	0.16198 (16)	0.1070 (4)	0.28537 (10)	0.0392 (7)
H9A	0.1669	−0.0341	0.2971	0.047*
H9B	0.1089	0.1217	0.2518	0.047*
C11	0.23363 (16)	0.1925 (4)	0.41676 (11)	0.0351 (7)
C12	0.27399 (18)	0.0011 (4)	0.42402 (13)	0.0476 (8)
H12	0.2520	−0.1008	0.3957	0.057*
C13	0.3461 (2)	−0.0390 (5)	0.47265 (14)	0.0588 (9)
H13	0.3731	−0.1668	0.4762	0.071*
C14	0.3783 (2)	0.1064 (6)	0.51574 (14)	0.0644 (10)
H14	0.4264	0.0781	0.5488	0.077*
C15	0.3385 (2)	0.2956 (5)	0.50947 (14)	0.0667 (11)
H15	0.3599	0.3957	0.5386	0.080*
C16	0.26703 (19)	0.3386 (4)	0.46049 (13)	0.0524 (8)
H16	0.2411	0.4675	0.4569	0.063*
C21	0.03106 (17)	0.1578 (4)	0.38258 (12)	0.0376 (7)
C22	−0.00707 (18)	0.2558 (5)	0.43068 (12)	0.0630 (9)
H22	0.0207	0.3761	0.4460	0.076*
C23	−0.0850 (2)	0.1835 (5)	0.45732 (15)	0.0738 (11)
H23	−0.1098	0.2555	0.4895	0.089*
C24	−0.1258 (2)	0.0041 (6)	0.43607 (15)	0.0647 (10)
H24	−0.1777	−0.0480	0.4543	0.078*
C25	−0.08946 (19)	−0.0959 (5)	0.38820 (14)	0.0613 (9)
H25	−0.1176	−0.2161	0.3732	0.074*
C26	−0.01139 (18)	−0.0229 (4)	0.36131 (13)	0.0501 (8)
H26	0.0129	−0.0948	0.3289	0.060*
B	0.1305 (2)	0.5365 (4)	0.33603 (16)	0.0559 (10)
HBA	0.1159	0.6183	0.3793	0.084*
HBB	0.0724	0.5649	0.2973	0.084*
HBC	0.1988	0.5887	0.3212	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0372 (4)	0.0318 (4)	0.0411 (4)	0.0017 (4)	0.0106 (3)	−0.0018 (4)
C1	0.0374 (15)	0.0400 (17)	0.0347 (15)	0.0016 (14)	0.0084 (12)	−0.0013 (14)
C2	0.0469 (18)	0.053 (2)	0.057 (2)	−0.0090 (16)	0.0182 (15)	−0.0117 (17)
C3	0.066 (2)	0.0493 (19)	0.064 (2)	−0.001 (2)	0.0165 (16)	−0.013 (2)
C3A	0.0412 (16)	0.0482 (19)	0.0387 (16)	0.0049 (15)	0.0062 (13)	−0.0020 (15)
C4	0.0532 (19)	0.055 (2)	0.0504 (19)	0.0123 (17)	0.0140 (15)	−0.0041 (17)
C5	0.0437 (18)	0.088 (3)	0.053 (2)	0.0091 (19)	0.0170 (15)	0.003 (2)
C6	0.0509 (19)	0.065 (3)	0.062 (2)	−0.0117 (17)	0.0162 (15)	−0.0048 (18)
C7	0.0468 (17)	0.046 (2)	0.0477 (17)	−0.0033 (15)	0.0116 (13)	−0.0050 (15)
C7A	0.0356 (15)	0.0379 (18)	0.0325 (15)	0.0034 (13)	0.0042 (12)	0.0003 (13)
C8	0.0442 (16)	0.0395 (17)	0.0427 (17)	−0.0020 (14)	0.0156 (13)	−0.0043 (14)
C9	0.0419 (16)	0.0417 (17)	0.0351 (15)	0.0039 (14)	0.0096 (12)	−0.0015 (14)
C11	0.0326 (14)	0.0375 (18)	0.0364 (15)	−0.0039 (12)	0.0088 (12)	−0.0004 (13)
C12	0.0466 (18)	0.043 (2)	0.0514 (19)	0.0032 (16)	−0.0003 (14)	−0.0052 (16)
C13	0.051 (2)	0.063 (2)	0.061 (2)	0.0110 (18)	0.0013 (16)	0.0062 (19)
C14	0.0446 (19)	0.099 (3)	0.048 (2)	−0.009 (2)	−0.0018 (15)	0.012 (2)
C15	0.071 (2)	0.071 (3)	0.055 (2)	−0.024 (2)	−0.0047 (17)	−0.0161 (19)
C16	0.058 (2)	0.0452 (19)	0.054 (2)	−0.0072 (16)	0.0045 (16)	−0.0082 (16)
C21	0.0304 (14)	0.0434 (18)	0.0405 (16)	0.0065 (13)	0.0104 (12)	0.0011 (14)
C22	0.0549 (19)	0.072 (2)	0.067 (2)	−0.010 (2)	0.0268 (16)	−0.025 (2)
C23	0.059 (2)	0.099 (3)	0.070 (2)	0.004 (2)	0.0336 (18)	−0.018 (2)
C24	0.0387 (18)	0.091 (3)	0.067 (2)	0.000 (2)	0.0172 (16)	0.020 (2)
C25	0.0466 (19)	0.061 (2)	0.078 (2)	−0.0104 (18)	0.0140 (17)	0.008 (2)
C26	0.0445 (18)	0.048 (2)	0.060 (2)	0.0007 (16)	0.0164 (15)	−0.0022 (17)
B	0.073 (3)	0.028 (2)	0.067 (3)	0.0080 (19)	0.012 (2)	0.0018 (18)

Geometric parameters (Å, º) top

P—C9	1.801 (2)	C9—H9B	0.9700
P—C21	1.802 (2)	C11—C16	1.380 (3)
P—C11	1.810 (3)	C11—C12	1.393 (3)
P—B	1.923 (3)	C12—C13	1.377 (3)
C1—C2	1.338 (3)	C12—H12	0.9300
C1—C7A	1.465 (3)	C13—C14	1.364 (4)
C1—C8	1.484 (3)	C13—H13	0.9300
C2—C3	1.502 (3)	C14—C15	1.376 (4)
C2—H2	0.9300	C14—H14	0.9300
C3—C3A	1.495 (3)	C15—C16	1.380 (4)
C3—H3A	0.9700	C15—H15	0.9300
C3—H3B	0.9700	C16—H16	0.9300
C3A—C4	1.375 (3)	C21—C22	1.364 (3)
C3A—C7A	1.398 (3)	C21—C26	1.391 (3)
C4—C5	1.378 (4)	C22—C23	1.374 (3)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.387 (4)	C23—C24	1.374 (4)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.388 (3)	C24—C25	1.355 (4)
C6—H6	0.9300	C24—H24	0.9300
C7—C7A	1.376 (3)	C25—C26	1.381 (3)
C7—H7	0.9300	C25—H25	0.9300
C8—C9	1.526 (3)	C26—H26	0.9300
C8—H8A	0.9700	B—HBA	1.1000
C8—H8B	0.9700	B—HBB	1.1000
C9—H9A	0.9700	B—HBC	1.1000

C9—P—C21	108.69 (12)	C8—C9—H9B	109.25
C9—P—C11	105.85 (12)	P—C9—H9B	109.25
C21—P—C11	104.86 (12)	H9A—C9—H9B	107.9
C9—P—B	112.41 (13)	C16—C11—C12	117.8 (3)
C21—P—B	112.24 (13)	C16—C11—P	119.6 (2)
C11—P—B	112.32 (14)	C12—C11—P	122.6 (2)
C2—C1—C7A	108.5 (2)	C13—C12—C11	120.8 (3)
C2—C1—C8	129.1 (2)	C13—C12—H12	119.60
C7A—C1—C8	122.2 (2)	C11—C12—H12	119.60
C1—C2—C3	110.9 (2)	C14—C13—C12	120.8 (3)
C1—C2—H2	124.53	C14—C13—H13	119.6
C3—C2—H2	124.53	C12—C13—H13	119.58
C3A—C3—C2	103.4 (2)	C13—C14—C15	118.9 (3)
C3A—C3—H3A	111.09	C13—C14—H14	120.5
C2—C3—H3A	111.09	C15—C14—H14	120.5
C3A—C3—H3B	111.09	C14—C15—C16	120.8 (3)
C2—C3—H3B	111.09	C14—C15—H15	119.6
H3A—C3—H3B	109.1	C16—C15—H15	119.6
C4—C3A—C7A	121.2 (3)	C15—C16—C11	120.7 (3)
C4—C3A—C3	130.9 (3)	C15—C16—H16	119.6
C7A—C3A—C3	107.9 (2)	C11—C16—H16	119.64
C3A—C4—C5	118.4 (3)	C22—C21—C26	117.3 (3)
C3A—C4—H4	120.78	C22—C21—P	119.9 (2)
C5—C4—H4	120.78	C26—C21—P	122.6 (2)
C4—C5—C6	120.9 (3)	C21—C22—C23	122.5 (3)
C4—C5—H5	119.55	C21—C22—H22	118.75
C6—C5—H5	119.55	C23—C22—H22	118.8
C5—C6—C7	120.5 (3)	C22—C23—C24	119.5 (3)
C5—C6—H6	119.73	C22—C23—H23	120.2
C7—C6—H6	119.73	C24—C23—H23	120.23
C7A—C7—C6	118.8 (3)	C25—C24—C23	119.1 (3)
C7A—C7—H7	120.58	C25—C24—H24	120.4
C6—C7—H7	120.58	C23—C24—H24	120.44
C7—C7A—C3A	120.1 (2)	C24—C25—C26	121.3 (3)
C7—C7A—C1	130.7 (3)	C24—C25—H25	119.4
C3A—C7A—C1	109.2 (2)	C26—C25—H25	119.35
C1—C8—C9	115.7 (2)	C25—C26—C21	120.2 (3)
C1—C8—H8A	108.35	C25—C26—H26	119.89
C9—C8—H8A	108.35	C21—C26—H26	119.89
C1—C8—H8B	108.35	P—B—HBA	109.47
C9—C8—H8B	108.35	P—B—HBB	109.47
H8A—C8—H8B	107.4	HBA—B—HBB	109.5
C8—C9—P	111.82 (18)	P—B—HBC	109.47
C8—C9—H9A	109.25	HBA—B—HBC	109.5
P—C9—H9A	109.25	HBB—B—HBC	109.5

C7A—C1—C2—C3	−0.4 (3)	C21—P—C11—C16	−98.9 (2)
C8—C1—C2—C3	−175.7 (3)	B—P—C11—C16	23.3 (3)
C1—C2—C3—C3A	1.0 (3)	C9—P—C11—C12	−35.3 (2)
C2—C3—C3A—C4	179.3 (3)	C21—P—C11—C12	79.5 (2)
C2—C3—C3A—C7A	−1.2 (3)	B—P—C11—C12	−158.3 (2)
C7A—C3A—C4—C5	0.2 (4)	C16—C11—C12—C13	−1.2 (4)
C3—C3A—C4—C5	179.6 (3)	P—C11—C12—C13	−179.6 (2)
C3A—C4—C5—C6	−0.3 (5)	C11—C12—C13—C14	1.4 (4)
C4—C5—C6—C7	0.5 (5)	C12—C13—C14—C15	−0.8 (5)
C5—C6—C7—C7A	−0.6 (4)	C13—C14—C15—C16	0.0 (5)
C6—C7—C7A—C3A	0.5 (4)	C14—C15—C16—C11	0.2 (5)
C6—C7—C7A—C1	179.4 (3)	C12—C11—C16—C15	0.3 (4)
C4—C3A—C7A—C7	−0.3 (4)	P—C11—C16—C15	178.8 (2)
C3—C3A—C7A—C7	−179.9 (2)	C9—P—C21—C22	−173.8 (2)
C4—C3A—C7A—C1	−179.4 (2)	C11—P—C21—C22	73.4 (3)
C3—C3A—C7A—C1	1.0 (3)	B—P—C21—C22	−48.8 (3)
C2—C1—C7A—C7	−179.4 (3)	C9—P—C21—C26	11.7 (3)
C8—C1—C7A—C7	−3.7 (4)	C11—P—C21—C26	−101.2 (2)
C2—C1—C7A—C3A	−0.4 (3)	B—P—C21—C26	136.6 (2)
C8—C1—C7A—C3A	175.3 (2)	C26—C21—C22—C23	−0.8 (4)
C2—C1—C8—C9	2.5 (4)	P—C21—C22—C23	−175.6 (2)
C7A—C1—C8—C9	−172.2 (2)	C21—C22—C23—C24	1.2 (5)
C1—C8—C9—P	165.44 (18)	C22—C23—C24—C25	−1.4 (5)
C21—P—C9—C8	−177.69 (18)	C23—C24—C25—C26	1.2 (5)
C11—P—C9—C8	−65.5 (2)	C24—C25—C26—C21	−0.8 (5)
B—P—C9—C8	57.4 (2)	C22—C21—C26—C25	0.6 (4)
C9—P—C11—C16	146.3 (2)	P—C21—C26—C25	175.2 (2)

Experimental details

Crystal data
Chemical formula	C₂₃H₂₄BP
M_r	342.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.061 (5), 6.644 (3), 21.018 (10)
β (°)	96.82 (3)
V (Å³)	1949.6 (15)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.88 × 0.12 × 0.02

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Integration (ABSORP in NRCVAX; Gabe et al, 1989)
T_min, T_max	0.695, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	30965, 3689, 1679
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.067, 0.64
No. of reflections	3689
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, locally modified NRC-2, NRC-2A (Ahmed et al., 1973), SHELXS93 (Sheldrick, 1990), NRCVAX (Gabe et al., 1989) and SHELXL93 (Sheldrick, 1993; 1996 revision), NRCVAX and SHELXL93.

Selected geometric parameters (Å, º) top

P—C9	1.801 (2)	C7—C7A	1.376 (3)
P—C21	1.802 (2)	C8—C9	1.526 (3)
P—C11	1.810 (3)	C11—C16	1.380 (3)
P—B	1.923 (3)	C11—C12	1.393 (3)
C1—C2	1.338 (3)	C12—C13	1.377 (3)
C1—C7A	1.465 (3)	C13—C14	1.364 (4)
C1—C8	1.484 (3)	C14—C15	1.376 (4)
C2—C3	1.502 (3)	C15—C16	1.380 (4)
C3—C3A	1.495 (3)	C21—C22	1.364 (3)
C3A—C4	1.375 (3)	C21—C26	1.391 (3)
C3A—C7A	1.398 (3)	C22—C23	1.374 (3)
C4—C5	1.378 (4)	C23—C24	1.374 (4)
C5—C6	1.387 (4)	C24—C25	1.355 (4)
C6—C7	1.388 (3)	C25—C26	1.381 (3)

C9—P—C21	108.69 (12)	C3A—C7A—C1	109.2 (2)
C9—P—C11	105.85 (12)	C1—C8—C9	115.7 (2)
C21—P—C11	104.86 (12)	C8—C9—P	111.82 (18)
C9—P—B	112.41 (13)	C16—C11—C12	117.8 (3)
C21—P—B	112.24 (13)	C16—C11—P	119.6 (2)
C11—P—B	112.32 (14)	C12—C11—P	122.6 (2)
C2—C1—C7A	108.5 (2)	C13—C12—C11	120.8 (3)
C2—C1—C8	129.1 (2)	C14—C13—C12	120.8 (3)
C7A—C1—C8	122.2 (2)	C13—C14—C15	118.9 (3)
C1—C2—C3	110.9 (2)	C14—C15—C16	120.8 (3)
C3A—C3—C2	103.4 (2)	C15—C16—C11	120.7 (3)
C4—C3A—C7A	121.2 (3)	C22—C21—C26	117.3 (3)
C4—C3A—C3	130.9 (3)	C22—C21—P	119.9 (2)
C7A—C3A—C3	107.9 (2)	C26—C21—P	122.6 (2)
C3A—C4—C5	118.4 (3)	C21—C22—C23	122.5 (3)
C4—C5—C6	120.9 (3)	C22—C23—C24	119.5 (3)
C5—C6—C7	120.5 (3)	C25—C24—C23	119.1 (3)
C7A—C7—C6	118.8 (3)	C24—C25—C26	121.3 (3)
C7—C7A—C3A	120.1 (2)	C25—C26—C21	120.2 (3)
C7—C7A—C1	130.7 (3)

C7A—C1—C2—C3	−0.4 (3)	C21—P—C11—C16	−98.9 (2)
C8—C1—C2—C3	−175.7 (3)	B—P—C11—C16	23.3 (3)
C1—C2—C3—C3A	1.0 (3)	C9—P—C11—C12	−35.3 (2)
C2—C3—C3A—C4	179.3 (3)	C21—P—C11—C12	79.5 (2)
C2—C3—C3A—C7A	−1.2 (3)	B—P—C11—C12	−158.3 (2)
C7A—C3A—C4—C5	0.2 (4)	C16—C11—C12—C13	−1.2 (4)
C3—C3A—C4—C5	179.6 (3)	P—C11—C12—C13	−179.6 (2)
C3A—C4—C5—C6	−0.3 (5)	C11—C12—C13—C14	1.4 (4)
C4—C5—C6—C7	0.5 (5)	C12—C13—C14—C15	−0.8 (5)
C5—C6—C7—C7A	−0.6 (4)	C13—C14—C15—C16	0.0 (5)
C6—C7—C7A—C3A	0.5 (4)	C14—C15—C16—C11	0.2 (5)
C6—C7—C7A—C1	179.4 (3)	C12—C11—C16—C15	0.3 (4)
C4—C3A—C7A—C7	−0.3 (4)	P—C11—C16—C15	178.8 (2)
C3—C3A—C7A—C7	−179.9 (2)	C9—P—C21—C22	−173.8 (2)
C4—C3A—C7A—C1	−179.4 (2)	C11—P—C21—C22	73.4 (3)
C3—C3A—C7A—C1	1.0 (3)	B—P—C21—C22	−48.8 (3)
C2—C1—C7A—C7	−179.4 (3)	C9—P—C21—C26	11.7 (3)
C8—C1—C7A—C7	−3.7 (4)	C11—P—C21—C26	−101.2 (2)
C2—C1—C7A—C3A	−0.4 (3)	B—P—C21—C26	136.6 (2)
C8—C1—C7A—C3A	175.3 (2)	C26—C21—C22—C23	−0.8 (4)
C2—C1—C8—C9	2.5 (4)	P—C21—C22—C23	−175.6 (2)
C7A—C1—C8—C9	−172.2 (2)	C21—C22—C23—C24	1.2 (5)
C1—C8—C9—P	165.44 (18)	C22—C23—C24—C25	−1.4 (5)
C21—P—C9—C8	−177.69 (18)	C23—C24—C25—C26	1.2 (5)
C11—P—C9—C8	−65.5 (2)	C24—C25—C26—C21	−0.8 (5)
B—P—C9—C8	57.4 (2)	C22—C21—C26—C25	0.6 (4)
C9—P—C11—C16	146.3 (2)	P—C21—C26—C25	175.2 (2)

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[2-(1H-Inden-3-yl)­ethyl]­di­phenyl­phos­phine-borane

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