Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009690/qa0339sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009690/qa0339Isup2.hkl |
CCDC reference: 150404
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%.
The space group was confirmed by PLATON (Spek, 1995). H atoms were constrained to the parent site using a riding model; SHELXL96 defaults, C—H 0.93–0.97 and B—H1.10 Å. The isotropic factors, Uiso, were adjusted to a value 50% higher than that of the parent site (B—H) and 20% higher (others). A final verification of possible voids was performed using the VOID routine of PLATON.
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.
C23H24BP | F(000) = 728 |
Mr = 342.20 | Dx = 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 |
Enraf–Nonius CAD-4 diffractometer | 1679 reflections with I > 2σ(I) |
Radiation source: normal-focus xray tube | Rint = 0.065 |
Graphite monochromator | θmax = 69.8°, θmin = 3.2° |
ω/2θ scans | h = −17→17 |
Absorption correction: integration (ABSORP in NRCVAX; Gabe et al, 1989) | k = −8→8 |
Tmin = 0.695, Tmax = 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 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(Fo2) + (0.0184P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.64 | (Δ/σ)max = 0.001 |
3689 reflections | Δρmax = 0.24 e Å−3 |
228 parameters | Δρmin = −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) |
C23H24BP | V = 1949.6 (15) Å3 |
Mr = 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)° |
Enraf–Nonius CAD-4 diffractometer | 1679 reflections with I > 2σ(I) |
Absorption correction: integration (ABSORP in NRCVAX; Gabe et al, 1989) | Rint = 0.065 |
Tmin = 0.695, Tmax = 0.978 | 5 standard reflections every 60 min |
30965 measured reflections | intensity decay: no decay, variation 0.0% |
3689 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 0.64 | Δρmax = 0.24 e Å−3 |
3689 reflections | Δρmin = −0.20 e Å−3 |
228 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. |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.695, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30965, 3689, 1679 |
Rint | 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 |
Δρmax, Δρmin (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.
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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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.