Abstract
The complete molecule of title compound, C58H58P4, is generated by a crystallographic twofold rotation axis that passes through the center of the C(methine)—C(methine) bond of length 1.582 (4) Å. The C—P bond lengths are 1.8824 (19) and 1.8991 (19) Å. The P—C—P angle of 109.69 (9)° is essentially equal to the expected value of 109.5° for a tetrahedral C atom. Although the C(methine)—P—C(aromatic) bond angles range from 102.67 (9) to 107.04 (9)°, the C(aromatic)—P—C(aromatic) bond angles of 96.72 (9) and 97.29 (9)° are significantly smaller. The steric demands of the o-tolyl groups cause deviations from the bond lengths and angles reported for its phenyl analog.
Related literature
For 1,1,2,2-tetrakis[(diphenyl)phosphino]ethane, see: Braunstein et al. (1995a
▶). For oxidative coupling of (bisphosphino)methanides, see: Braunstein et al. (1995b
▶); Schmidbaur & Deschler (1983 ▶). 
Experimental
Crystal data
C58H58P4
M r = 878.92
Monoclinic,
a = 21.8875 (11) Å
b = 10.9702 (6) Å
c = 19.691 (1) Å
β = 90.761 (3)°
V = 4727.6 (4) Å3
Z = 4
Mo Kα radiation
μ = 0.20 mm−1
T = 193 K
0.42 × 0.40 × 0.24 mm
Data collection
Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.942, T max = 0.976
19717 measured reflections
4345 independent reflections
3343 reflections with I > 2σ(I)
R int = 0.049
Refinement
R[F 2 > 2σ(F 2)] = 0.039
wR(F 2) = 0.102
S = 1.01
4345 reflections
284 parameters
H-atom parameters not refined
Δρmax = 0.35 e Å−3
Δρmin = −0.19 e Å−3
Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT, XPREP (Bruker, 2005 ▶) and SADABS (Bruker, 2007 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and CrystalMaker (CrystalMaker, 1994 ▶); software used to prepare material for publication: XCIF (Bruker, 2005 ▶).
Supplementary Material
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032942/ng2629sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032942/ng2629Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
We thank the National Science Foundation (grant CHE-0548107) for support of this work. The Materials Chemistry Laboratory at the University of Illinois was supported in part by grants from the NSF (CHE 95–03145 and CHE 03–43032).
supplementary crystallographic information
Comment
The title compound, [P(o-tolyl)2]2CH—CH[P(o-tolyl)2]2, was unintentionally obtained as one of two isomeric products from the reaction of Li{CH[P(o-tolyl)2]2} with PdCl2. It is formed by the C—C cross-coupling of two CH[P(o-tolyl)2]2 units, whereas its isomer is a P—C coupling product. Oxidative coupling reactions involving (bisphosphino)methanide compounds have been reported (Braunstein et al., 1995a; Braunstein et al., 1995b; Schmidbaur & Deschler, 1983).
The title compound crystallizes in C2/c, whereas the space group is P21/n for its phenyl analog, [P(Ph)2]2CH—CH[P(Ph)2]2 (Braunstein et al., 1995a). The structure of the title compound has a twofold rotation axis through the center of the C(methine)–C(methine) bond (Fig. 1). The atomic positions of only one CH[P(o-tolyl)2]2 unit were determined, and the atomic positions of the other unit are related by the symmetry operator (1 - x, y, 0.5 - z). The methine hydrogen atoms adopt a gauche conformation that likely maximizes the π interactions of the aromatic rings. The C1(methine)—C1(methine) bond length is 1.582 (4) Å, and its C1—P bond lengths are 1.8824 (19) and 1.8991 (19) Å. The P1—C1—P2 bond angle of 109.69 (9)° essentially equals the tetrahedral value of 109.5°. The C(methine)—P—C(aromatic) bond angles range from 102.67 (9) to 107.04 (9)°, whereas the C(aromatic)—P—C(aromatic) bond angles of 96.72 (9) and 97.29 (9)° are significantly smaller. The steric demands of the o-tolyl groups in C58H58P4 cause deviations from the bond lengths and angles reported for the related phenyl compound.
Like its phenyl analog, the title compound is chiral in the solid form, and its room temperature NMR spectra reveal that its chirality is retained in solution. The compound has an AA'BB' 31P spin system, and its methine protons are inequivalent in the 1H NMR spectrum.
Experimental
The title compound, C58H58P4, is one of two isomeric products. Under an N2 atmosphere, n-BuLi (0.63 ml of a 1.6 M solution in hexanes, 1.0 mmol) was added over 1 h to a solution of bis(di-o-tolylphosphino)methane (0.44 g, 1.0 mmol) in toluene (5 ml). The solution was refluxed for 1 h and the solvent was removed under vacuum. The solid residue was redissolved in THF (5 ml) and added over 1 h to a suspension of PdCl2 in toluene (6 ml). The mixture was stirred overnight and the solvent was removed under vacuum. Toluene (8 ml) and pentane (50 ml) were added to dissolve the residue, and the mixture was filtered through Celite. The filtrate was concentrated to 3 ml and layered with pentane (15 ml). Yellow crystals of the title compound were obtained after 1 week at room temperature. 1H NMR (CDCl3): δ 1.65–2.18 (m, C6H4CH3), 3.27 (br s, CH), 4.55 (m, CH), 5.76 (br s, C6H4CH3), 6.05 (br s, C6H4CH3), 6.81–7.55 (m, C6H4CH3), 8.23 (br s, C6H4CH3). 31P {1H} NMR (CDCl3): δ -16.3 (m, PA), -39.3 (m, PB) of an AA'BB' spin system.
Refinement
A structural model consisting of the molecule was developed using the Bruker SHELXTL suite of programs. Most of the non-hydrogen containing atoms were found in the E-map generated from the direct-methods solution. The remaining non-hydrogen atoms were located after full-matrix least squares / difference Fourier cycles were performed. All non-hydrogen atoms were refined with anisotropic displacement parameters. Methyl H atom positions, R—CH3, were optimized by rotation about R—C bonds with idealized C—H, R—H and H···H distances. Remaining H atoms were included as riding idealized contributors. Methyl H atom U's were assigned as 1.5 times Ueq of the carrier atom; remaining H atom U's were assigned as 1.2 times carrier Ueq.
Figures
Fig. 1.
Molecular structure of the title compound showing 35% probability ellipsoids for non-H atoms and circles of arbitrary size for H atoms. The unlabeled atoms are related to the labeled atoms by the symmetry operator (1 - x, y, 0.5 - z).
Crystal data
| C58H58P4 | F(000) = 1864 |
| Mr = 878.92 | Dx = 1.235 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 3541 reflections |
| a = 21.8875 (11) Å | θ = 2.8–26.4° |
| b = 10.9702 (6) Å | µ = 0.20 mm−1 |
| c = 19.691 (1) Å | T = 193 K |
| β = 90.761 (3)° | Prism, yellow |
| V = 4727.6 (4) Å3 | 0.42 × 0.40 × 0.24 mm |
| Z = 4 |
Data collection
| Bruker Kappa APEXII CCD diffractometer | 4345 independent reflections |
| Radiation source: fine-focus sealed tube | 3343 reflections with I > 2σ(I) |
| graphite | Rint = 0.049 |
| φ and ω scans | θmax = 25.4°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −26→26 |
| Tmin = 0.942, Tmax = 0.976 | k = −13→11 |
| 19717 measured reflections | l = −21→23 |
Refinement
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.102 | H-atom parameters not refined |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.0477P)2 + 3.4164P] where P = (Fo2 + 2Fc2)/3 |
| 4345 reflections | (Δ/σ)max = 0.001 |
| 284 parameters | Δρmax = 0.35 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
Special details
| Experimental. One distinct cell was identified using APEX2 (Bruker, 2004). Four frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2005) then corrected for absorption by integration using SHELXTL/XPREP V2005/2 (Bruker, 2005) before using SAINT/SADABS (Bruker, 2005) to sort, merge,and scale the combined data. No decay correction was applied. |
| 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. Structure was phased by direct methods (Sheldrick, 2008). Systematic conditions suggested the ambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F2. The highest peaks in the final difference Fourier map were in the vicinity of atoms P1 and P2; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed some dependence on amplitude but little on resolution. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| P1 | 0.39722 (2) | 0.68981 (5) | 0.23551 (3) | 0.02565 (14) | |
| P2 | 0.48535 (2) | 0.83242 (5) | 0.33033 (2) | 0.02367 (14) | |
| C1 | 0.47465 (8) | 0.68809 (17) | 0.27827 (9) | 0.0222 (4) | |
| H1A | 0.4790 | 0.6145 | 0.3079 | 0.027* | |
| C2 | 0.39830 (9) | 0.54854 (18) | 0.18376 (10) | 0.0280 (5) | |
| C3 | 0.36720 (9) | 0.5468 (2) | 0.12096 (10) | 0.0308 (5) | |
| C4 | 0.36966 (10) | 0.4409 (2) | 0.08185 (11) | 0.0401 (6) | |
| H4A | 0.3490 | 0.4391 | 0.0391 | 0.048* | |
| C5 | 0.40112 (11) | 0.3389 (2) | 0.10330 (12) | 0.0433 (6) | |
| H5A | 0.4026 | 0.2686 | 0.0752 | 0.052* | |
| C6 | 0.43039 (11) | 0.3389 (2) | 0.16554 (12) | 0.0414 (6) | |
| H6A | 0.4516 | 0.2685 | 0.1811 | 0.050* | |
| C7 | 0.42855 (10) | 0.44320 (19) | 0.20526 (11) | 0.0345 (5) | |
| H7A | 0.4485 | 0.4429 | 0.2484 | 0.041* | |
| C8 | 0.33175 (10) | 0.6547 (2) | 0.09454 (11) | 0.0376 (5) | |
| H8A | 0.3234 | 0.6441 | 0.0459 | 0.056* | |
| H8B | 0.3557 | 0.7292 | 0.1018 | 0.056* | |
| H8C | 0.2931 | 0.6612 | 0.1188 | 0.056* | |
| C9 | 0.34259 (9) | 0.63472 (19) | 0.30004 (10) | 0.0305 (5) | |
| C10 | 0.28290 (10) | 0.6830 (2) | 0.30017 (11) | 0.0385 (6) | |
| C11 | 0.24123 (11) | 0.6334 (3) | 0.34590 (13) | 0.0513 (7) | |
| H11A | 0.2008 | 0.6650 | 0.3466 | 0.062* | |
| C12 | 0.25671 (12) | 0.5408 (3) | 0.38986 (13) | 0.0561 (7) | |
| H12A | 0.2272 | 0.5089 | 0.4200 | 0.067* | |
| C13 | 0.31522 (12) | 0.4946 (2) | 0.38997 (12) | 0.0480 (6) | |
| H13A | 0.3265 | 0.4312 | 0.4205 | 0.058* | |
| C14 | 0.35750 (10) | 0.5414 (2) | 0.34532 (11) | 0.0369 (5) | |
| H14A | 0.3978 | 0.5090 | 0.3455 | 0.044* | |
| C15 | 0.26167 (11) | 0.7842 (2) | 0.25435 (13) | 0.0495 (6) | |
| H15A | 0.2318 | 0.8346 | 0.2781 | 0.074* | |
| H15B | 0.2427 | 0.7496 | 0.2133 | 0.074* | |
| H15C | 0.2967 | 0.8345 | 0.2417 | 0.074* | |
| C16 | 0.40878 (9) | 0.87239 (19) | 0.36281 (10) | 0.0276 (4) | |
| C17 | 0.37778 (10) | 0.9723 (2) | 0.33442 (11) | 0.0353 (5) | |
| C18 | 0.32210 (11) | 1.0061 (2) | 0.36232 (12) | 0.0470 (6) | |
| H18A | 0.3005 | 1.0731 | 0.3430 | 0.056* | |
| C19 | 0.29730 (11) | 0.9465 (2) | 0.41646 (13) | 0.0481 (7) | |
| H19A | 0.2592 | 0.9722 | 0.4341 | 0.058* | |
| C20 | 0.32791 (10) | 0.8488 (2) | 0.44523 (12) | 0.0389 (5) | |
| H20A | 0.3112 | 0.8068 | 0.4828 | 0.047* | |
| C21 | 0.38290 (9) | 0.8131 (2) | 0.41877 (10) | 0.0311 (5) | |
| H21A | 0.4040 | 0.7463 | 0.4389 | 0.037* | |
| C22 | 0.40310 (13) | 1.0441 (2) | 0.27621 (13) | 0.0538 (7) | |
| H22A | 0.3741 | 1.1083 | 0.2631 | 0.081* | |
| H22B | 0.4097 | 0.9897 | 0.2375 | 0.081* | |
| H22C | 0.4420 | 1.0812 | 0.2901 | 0.081* | |
| C23 | 0.52007 (8) | 0.78697 (18) | 0.41210 (9) | 0.0244 (4) | |
| C24 | 0.55118 (9) | 0.87983 (19) | 0.44804 (10) | 0.0307 (5) | |
| C25 | 0.57354 (11) | 0.8554 (2) | 0.51278 (11) | 0.0395 (6) | |
| H25A | 0.5939 | 0.9182 | 0.5374 | 0.047* | |
| C26 | 0.56695 (11) | 0.7426 (2) | 0.54230 (11) | 0.0410 (6) | |
| H26A | 0.5822 | 0.7284 | 0.5870 | 0.049* | |
| C27 | 0.53823 (10) | 0.6504 (2) | 0.50693 (11) | 0.0385 (5) | |
| H27A | 0.5343 | 0.5718 | 0.5267 | 0.046* | |
| C28 | 0.51505 (9) | 0.67275 (19) | 0.44232 (10) | 0.0308 (5) | |
| H28A | 0.4953 | 0.6087 | 0.4181 | 0.037* | |
| C29 | 0.56121 (12) | 1.0050 (2) | 0.41859 (12) | 0.0467 (6) | |
| H29A | 0.5803 | 1.0576 | 0.4530 | 0.070* | |
| H29B | 0.5218 | 1.0399 | 0.4044 | 0.070* | |
| H29C | 0.5880 | 0.9989 | 0.3792 | 0.070* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| P1 | 0.0244 (3) | 0.0252 (3) | 0.0273 (3) | −0.0011 (2) | −0.0027 (2) | −0.0013 (2) |
| P2 | 0.0255 (3) | 0.0219 (3) | 0.0236 (3) | 0.0003 (2) | −0.0008 (2) | −0.0012 (2) |
| C1 | 0.0225 (10) | 0.0212 (10) | 0.0230 (9) | 0.0001 (8) | 0.0004 (8) | 0.0001 (8) |
| C2 | 0.0265 (10) | 0.0289 (11) | 0.0286 (11) | −0.0079 (9) | 0.0040 (8) | −0.0023 (9) |
| C3 | 0.0264 (11) | 0.0381 (12) | 0.0279 (11) | −0.0111 (9) | 0.0049 (8) | −0.0030 (9) |
| C4 | 0.0375 (13) | 0.0503 (15) | 0.0325 (12) | −0.0131 (11) | 0.0014 (10) | −0.0090 (11) |
| C5 | 0.0476 (14) | 0.0360 (14) | 0.0467 (14) | −0.0114 (11) | 0.0092 (11) | −0.0157 (11) |
| C6 | 0.0487 (14) | 0.0270 (12) | 0.0486 (14) | −0.0040 (11) | 0.0087 (11) | −0.0049 (11) |
| C7 | 0.0402 (13) | 0.0300 (12) | 0.0335 (12) | −0.0061 (10) | 0.0035 (9) | −0.0025 (9) |
| C8 | 0.0323 (12) | 0.0480 (14) | 0.0325 (11) | −0.0062 (11) | −0.0042 (9) | −0.0013 (10) |
| C9 | 0.0270 (11) | 0.0340 (12) | 0.0305 (11) | −0.0058 (9) | 0.0004 (9) | −0.0101 (9) |
| C10 | 0.0279 (11) | 0.0482 (15) | 0.0393 (12) | −0.0022 (10) | −0.0013 (9) | −0.0190 (11) |
| C11 | 0.0289 (12) | 0.077 (2) | 0.0488 (15) | −0.0046 (13) | 0.0070 (11) | −0.0227 (15) |
| C12 | 0.0441 (15) | 0.078 (2) | 0.0463 (15) | −0.0204 (15) | 0.0180 (12) | −0.0119 (15) |
| C13 | 0.0509 (15) | 0.0532 (16) | 0.0401 (13) | −0.0119 (13) | 0.0099 (11) | −0.0006 (12) |
| C14 | 0.0344 (12) | 0.0395 (13) | 0.0368 (12) | −0.0050 (10) | 0.0058 (10) | −0.0041 (10) |
| C15 | 0.0350 (13) | 0.0583 (17) | 0.0550 (15) | 0.0100 (12) | −0.0064 (11) | −0.0154 (13) |
| C16 | 0.0265 (10) | 0.0278 (11) | 0.0283 (10) | 0.0020 (9) | −0.0047 (8) | −0.0078 (9) |
| C17 | 0.0386 (12) | 0.0362 (13) | 0.0310 (11) | 0.0101 (10) | −0.0051 (9) | −0.0064 (10) |
| C18 | 0.0418 (14) | 0.0529 (16) | 0.0460 (14) | 0.0241 (12) | −0.0066 (11) | −0.0060 (12) |
| C19 | 0.0307 (13) | 0.0646 (18) | 0.0491 (15) | 0.0133 (12) | 0.0015 (11) | −0.0127 (13) |
| C20 | 0.0297 (12) | 0.0483 (15) | 0.0387 (12) | −0.0013 (11) | 0.0036 (10) | −0.0087 (11) |
| C21 | 0.0284 (11) | 0.0323 (12) | 0.0325 (11) | 0.0027 (9) | −0.0001 (9) | −0.0067 (9) |
| C22 | 0.0684 (18) | 0.0474 (16) | 0.0456 (15) | 0.0237 (14) | 0.0029 (13) | 0.0111 (12) |
| C23 | 0.0215 (10) | 0.0274 (11) | 0.0244 (10) | 0.0041 (8) | 0.0018 (8) | −0.0011 (8) |
| C24 | 0.0315 (11) | 0.0307 (12) | 0.0299 (11) | 0.0024 (9) | −0.0028 (9) | −0.0066 (9) |
| C25 | 0.0444 (14) | 0.0397 (14) | 0.0343 (12) | 0.0005 (11) | −0.0072 (10) | −0.0090 (11) |
| C26 | 0.0458 (14) | 0.0513 (15) | 0.0258 (11) | 0.0071 (12) | −0.0086 (10) | −0.0026 (11) |
| C27 | 0.0453 (13) | 0.0378 (13) | 0.0324 (12) | 0.0023 (11) | −0.0007 (10) | 0.0067 (10) |
| C28 | 0.0327 (11) | 0.0311 (12) | 0.0284 (10) | −0.0019 (9) | −0.0011 (9) | −0.0011 (9) |
| C29 | 0.0640 (16) | 0.0334 (13) | 0.0422 (14) | −0.0106 (12) | −0.0127 (12) | −0.0073 (11) |
Geometric parameters (Å, °)
| P1—C2 | 1.855 (2) | C14—H14A | 0.9500 |
| P1—C9 | 1.857 (2) | C15—H15A | 0.9800 |
| P1—C1 | 1.8824 (19) | C15—H15B | 0.9800 |
| P2—C23 | 1.8401 (19) | C15—H15C | 0.9800 |
| P2—C16 | 1.854 (2) | C16—C17 | 1.402 (3) |
| P2—C1 | 1.8991 (19) | C16—C21 | 1.405 (3) |
| C1—C1i | 1.582 (4) | C17—C18 | 1.394 (3) |
| C1—H1A | 1.0000 | C17—C22 | 1.502 (3) |
| C2—C7 | 1.395 (3) | C18—C19 | 1.369 (3) |
| C2—C3 | 1.404 (3) | C18—H18A | 0.9500 |
| C3—C4 | 1.396 (3) | C19—C20 | 1.381 (3) |
| C3—C8 | 1.504 (3) | C19—H19A | 0.9500 |
| C4—C5 | 1.377 (3) | C20—C21 | 1.375 (3) |
| C4—H4A | 0.9500 | C20—H20A | 0.9500 |
| C5—C6 | 1.375 (3) | C21—H21A | 0.9500 |
| C5—H5A | 0.9500 | C22—H22A | 0.9800 |
| C6—C7 | 1.387 (3) | C22—H22B | 0.9800 |
| C6—H6A | 0.9500 | C22—H22C | 0.9800 |
| C7—H7A | 0.9500 | C23—C28 | 1.392 (3) |
| C8—H8A | 0.9800 | C23—C24 | 1.410 (3) |
| C8—H8B | 0.9800 | C24—C25 | 1.385 (3) |
| C8—H8C | 0.9800 | C24—C29 | 1.508 (3) |
| C9—C14 | 1.394 (3) | C25—C26 | 1.376 (3) |
| C9—C10 | 1.410 (3) | C25—H25A | 0.9500 |
| C10—C11 | 1.400 (3) | C26—C27 | 1.375 (3) |
| C10—C15 | 1.501 (3) | C26—H26A | 0.9500 |
| C11—C12 | 1.374 (4) | C27—C28 | 1.385 (3) |
| C11—H11A | 0.9500 | C27—H27A | 0.9500 |
| C12—C13 | 1.377 (4) | C28—H28A | 0.9500 |
| C12—H12A | 0.9500 | C29—H29A | 0.9800 |
| C13—C14 | 1.383 (3) | C29—H29B | 0.9800 |
| C13—H13A | 0.9500 | C29—H29C | 0.9800 |
| C2—P1—C9 | 96.72 (9) | C10—C15—H15A | 109.5 |
| C2—P1—C1 | 102.67 (9) | C10—C15—H15B | 109.5 |
| C9—P1—C1 | 105.95 (9) | H15A—C15—H15B | 109.5 |
| C23—P2—C16 | 97.29 (9) | C10—C15—H15C | 109.5 |
| C23—P2—C1 | 107.04 (9) | H15A—C15—H15C | 109.5 |
| C16—P2—C1 | 106.12 (8) | H15B—C15—H15C | 109.5 |
| C1i—C1—P1 | 108.72 (16) | C17—C16—C21 | 118.48 (19) |
| C1i—C1—P2 | 107.29 (9) | C17—C16—P2 | 118.84 (16) |
| P1—C1—P2 | 109.69 (9) | C21—C16—P2 | 122.44 (15) |
| C1i—C1—H1A | 110.4 | C18—C17—C16 | 118.2 (2) |
| P1—C1—H1A | 110.4 | C18—C17—C22 | 119.7 (2) |
| P2—C1—H1A | 110.4 | C16—C17—C22 | 122.2 (2) |
| C7—C2—C3 | 118.62 (19) | C19—C18—C17 | 122.5 (2) |
| C7—C2—P1 | 122.33 (15) | C19—C18—H18A | 118.7 |
| C3—C2—P1 | 119.05 (16) | C17—C18—H18A | 118.7 |
| C4—C3—C2 | 118.4 (2) | C18—C19—C20 | 119.7 (2) |
| C4—C3—C8 | 119.20 (19) | C18—C19—H19A | 120.2 |
| C2—C3—C8 | 122.41 (19) | C20—C19—H19A | 120.2 |
| C5—C4—C3 | 122.0 (2) | C21—C20—C19 | 119.2 (2) |
| C5—C4—H4A | 119.0 | C21—C20—H20A | 120.4 |
| C3—C4—H4A | 119.0 | C19—C20—H20A | 120.4 |
| C6—C5—C4 | 119.9 (2) | C20—C21—C16 | 121.9 (2) |
| C6—C5—H5A | 120.1 | C20—C21—H21A | 119.0 |
| C4—C5—H5A | 120.1 | C16—C21—H21A | 119.0 |
| C5—C6—C7 | 119.1 (2) | C17—C22—H22A | 109.5 |
| C5—C6—H6A | 120.4 | C17—C22—H22B | 109.5 |
| C7—C6—H6A | 120.4 | H22A—C22—H22B | 109.5 |
| C6—C7—C2 | 122.0 (2) | C17—C22—H22C | 109.5 |
| C6—C7—H7A | 119.0 | H22A—C22—H22C | 109.5 |
| C2—C7—H7A | 119.0 | H22B—C22—H22C | 109.5 |
| C3—C8—H8A | 109.5 | C28—C23—C24 | 118.42 (18) |
| C3—C8—H8B | 109.5 | C28—C23—P2 | 125.72 (15) |
| H8A—C8—H8B | 109.5 | C24—C23—P2 | 115.75 (15) |
| C3—C8—H8C | 109.5 | C25—C24—C23 | 119.0 (2) |
| H8A—C8—H8C | 109.5 | C25—C24—C29 | 118.57 (19) |
| H8B—C8—H8C | 109.5 | C23—C24—C29 | 122.45 (18) |
| C14—C9—C10 | 118.9 (2) | C26—C25—C24 | 121.6 (2) |
| C14—C9—P1 | 121.96 (16) | C26—C25—H25A | 119.2 |
| C10—C9—P1 | 118.96 (17) | C24—C25—H25A | 119.2 |
| C11—C10—C9 | 117.9 (2) | C27—C26—C25 | 119.8 (2) |
| C11—C10—C15 | 118.3 (2) | C27—C26—H26A | 120.1 |
| C9—C10—C15 | 123.8 (2) | C25—C26—H26A | 120.1 |
| C12—C11—C10 | 122.3 (2) | C26—C27—C28 | 119.6 (2) |
| C12—C11—H11A | 118.8 | C26—C27—H27A | 120.2 |
| C10—C11—H11A | 118.8 | C28—C27—H27A | 120.2 |
| C11—C12—C13 | 119.6 (2) | C27—C28—C23 | 121.5 (2) |
| C11—C12—H12A | 120.2 | C27—C28—H28A | 119.3 |
| C13—C12—H12A | 120.2 | C23—C28—H28A | 119.3 |
| C12—C13—C14 | 119.5 (3) | C24—C29—H29A | 109.5 |
| C12—C13—H13A | 120.2 | C24—C29—H29B | 109.5 |
| C14—C13—H13A | 120.2 | H29A—C29—H29B | 109.5 |
| C13—C14—C9 | 121.7 (2) | C24—C29—H29C | 109.5 |
| C13—C14—H14A | 119.1 | H29A—C29—H29C | 109.5 |
| C9—C14—H14A | 119.1 | H29B—C29—H29C | 109.5 |
| C2—P1—C1—C1i | 59.35 (7) | C11—C12—C13—C14 | −0.6 (4) |
| C9—P1—C1—C1i | 160.24 (7) | C12—C13—C14—C9 | 0.2 (4) |
| C2—P1—C1—P2 | 176.38 (9) | C10—C9—C14—C13 | 0.3 (3) |
| C9—P1—C1—P2 | −82.73 (11) | P1—C9—C14—C13 | −175.23 (18) |
| C23—P2—C1—C1i | −105.45 (15) | C23—P2—C16—C17 | 142.76 (16) |
| C16—P2—C1—C1i | 151.44 (14) | C1—P2—C16—C17 | −107.09 (16) |
| C23—P2—C1—P1 | 136.62 (9) | C23—P2—C16—C21 | −31.53 (18) |
| C16—P2—C1—P1 | 33.51 (12) | C1—P2—C16—C21 | 78.62 (18) |
| C9—P1—C2—C7 | −73.92 (18) | C21—C16—C17—C18 | −1.4 (3) |
| C1—P1—C2—C7 | 34.14 (19) | P2—C16—C17—C18 | −175.89 (17) |
| C9—P1—C2—C3 | 105.52 (16) | C21—C16—C17—C22 | 177.7 (2) |
| C1—P1—C2—C3 | −146.42 (15) | P2—C16—C17—C22 | 3.2 (3) |
| C7—C2—C3—C4 | −2.1 (3) | C16—C17—C18—C19 | 0.8 (4) |
| P1—C2—C3—C4 | 178.47 (15) | C22—C17—C18—C19 | −178.3 (2) |
| C7—C2—C3—C8 | 178.14 (19) | C17—C18—C19—C20 | −0.1 (4) |
| P1—C2—C3—C8 | −1.3 (3) | C18—C19—C20—C21 | −0.1 (4) |
| C2—C3—C4—C5 | 0.5 (3) | C19—C20—C21—C16 | −0.6 (3) |
| C8—C3—C4—C5 | −179.7 (2) | C17—C16—C21—C20 | 1.3 (3) |
| C3—C4—C5—C6 | 1.2 (3) | P2—C16—C21—C20 | 175.60 (17) |
| C4—C5—C6—C7 | −1.1 (3) | C16—P2—C23—C28 | 83.90 (18) |
| C5—C6—C7—C2 | −0.5 (3) | C1—P2—C23—C28 | −25.49 (19) |
| C3—C2—C7—C6 | 2.2 (3) | C16—P2—C23—C24 | −92.16 (16) |
| P1—C2—C7—C6 | −178.40 (16) | C1—P2—C23—C24 | 158.45 (15) |
| C2—P1—C9—C14 | 67.02 (18) | C28—C23—C24—C25 | −2.3 (3) |
| C1—P1—C9—C14 | −38.25 (19) | P2—C23—C24—C25 | 174.03 (16) |
| C2—P1—C9—C10 | −108.55 (17) | C28—C23—C24—C29 | 177.5 (2) |
| C1—P1—C9—C10 | 146.18 (16) | P2—C23—C24—C29 | −6.1 (3) |
| C14—C9—C10—C11 | −0.4 (3) | C23—C24—C25—C26 | 1.0 (3) |
| P1—C9—C10—C11 | 175.27 (16) | C29—C24—C25—C26 | −178.9 (2) |
| C14—C9—C10—C15 | 179.4 (2) | C24—C25—C26—C27 | 0.8 (4) |
| P1—C9—C10—C15 | −4.9 (3) | C25—C26—C27—C28 | −1.3 (3) |
| C9—C10—C11—C12 | 0.0 (3) | C26—C27—C28—C23 | −0.1 (3) |
| C15—C10—C11—C12 | −179.8 (2) | C24—C23—C28—C27 | 1.9 (3) |
| C10—C11—C12—C13 | 0.5 (4) | P2—C23—C28—C27 | −174.07 (16) |
Symmetry codes: (i) −x+1, y, −z+1/2.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2629).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032942/ng2629sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032942/ng2629Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report