organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1,1,2,2-Tetra­kis(di-o-tolyl­phosphino)ethane

aDePaul University, Department of Chemistry, 1110 West Belden Avenue, Chicago, Illinois 60614, USA, and bUniversity of Illinois, School of Chemical Sciences, Box 59-1, 505 South Mathews Avenue, Urbana, Illinois 61801, USA
*Correspondence e-mail: qshelby@depaul.edu

(Received 18 August 2009; accepted 19 August 2009; online 26 August 2009)

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[Braunstein, P., Hasselbring, R., DeCian, A. & Fischer, J. (1995a). Bull. Soc. Chim. Fr. 132, 691-695.]). For oxidative coupling of (bis­phosphino)methanides, see: Braunstein et al. (1995b[Braunstein, P., Hasselbring, R., Tiripicchio, A. & Ugozzoli, F. (1995b). J. Chem. Soc. Chem. Commun. pp. 37-38.]); Schmidbaur & Deschler (1983[Schmidbaur, H. & Deschler, U. (1983). Chem. Ber. 116, 1386-1392.]).

[Scheme 1]

Experimental

Crystal data
  • C58H58P4

  • Mr = 878.92

  • Monoclinic, C 2/c

  • 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[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.942, Tmax = 0.976

  • 19717 measured reflections

  • 4345 independent reflections

  • 3343 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 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[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT, XPREP (Bruker, 2005[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) and SADABS (Bruker, 2007[Bruker (2007). SADABS and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and CrystalMaker (CrystalMaker, 1994[CrystalMaker (1994). CrystalMaker. CrystalMaker Software Ltd, Oxford, England. URL: www.CrystalMaker.com.]); software used to prepare material for publication: XCIF (Bruker, 2005[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]).

Supporting information


Comment top

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.

Related literature top

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 top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005), XPREP (Bruker, 2005) and SADABS (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2005) and CrystalMaker (CrystalMaker, 1994); software used to prepare material for publication: XCIF (Bruker, 2005).

Figures top
[Figure 1] 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).
1,1,2,2-Tetrakis(di-o-tolylphosphino)ethane top
Crystal data top
C58H58P4F(000) = 1864
Mr = 878.92Dx = 1.235 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3541 reflections
a = 21.8875 (11) Åθ = 2.8–26.4°
b = 10.9702 (6) ŵ = 0.20 mm1
c = 19.691 (1) ÅT = 193 K
β = 90.761 (3)°Prism, yellow
V = 4727.6 (4) Å30.42 × 0.40 × 0.24 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4345 independent reflections
Radiation source: fine-focus sealed tube3343 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ϕ and ω scansθmax = 25.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 2626
Tmin = 0.942, Tmax = 0.976k = 1311
19717 measured reflectionsl = 2123
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-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 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C58H58P4V = 4727.6 (4) Å3
Mr = 878.92Z = 4
Monoclinic, C2/cMo Kα radiation
a = 21.8875 (11) ŵ = 0.20 mm1
b = 10.9702 (6) ÅT = 193 K
c = 19.691 (1) Å0.42 × 0.40 × 0.24 mm
β = 90.761 (3)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4345 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3343 reflections with I > 2σ(I)
Tmin = 0.942, Tmax = 0.976Rint = 0.049
19717 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.102H-atom parameters not refined
S = 1.01Δρmax = 0.35 e Å3
4345 reflectionsΔρmin = 0.19 e Å3
284 parameters
Special details top

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) top
xyzUiso*/Ueq
P10.39722 (2)0.68981 (5)0.23551 (3)0.02565 (14)
P20.48535 (2)0.83242 (5)0.33033 (2)0.02367 (14)
C10.47465 (8)0.68809 (17)0.27827 (9)0.0222 (4)
H1A0.47900.61450.30790.027*
C20.39830 (9)0.54854 (18)0.18376 (10)0.0280 (5)
C30.36720 (9)0.5468 (2)0.12096 (10)0.0308 (5)
C40.36966 (10)0.4409 (2)0.08185 (11)0.0401 (6)
H4A0.34900.43910.03910.048*
C50.40112 (11)0.3389 (2)0.10330 (12)0.0433 (6)
H5A0.40260.26860.07520.052*
C60.43039 (11)0.3389 (2)0.16554 (12)0.0414 (6)
H6A0.45160.26850.18110.050*
C70.42855 (10)0.44320 (19)0.20526 (11)0.0345 (5)
H7A0.44850.44290.24840.041*
C80.33175 (10)0.6547 (2)0.09454 (11)0.0376 (5)
H8A0.32340.64410.04590.056*
H8B0.35570.72920.10180.056*
H8C0.29310.66120.11880.056*
C90.34259 (9)0.63472 (19)0.30004 (10)0.0305 (5)
C100.28290 (10)0.6830 (2)0.30017 (11)0.0385 (6)
C110.24123 (11)0.6334 (3)0.34590 (13)0.0513 (7)
H11A0.20080.66500.34660.062*
C120.25671 (12)0.5408 (3)0.38986 (13)0.0561 (7)
H12A0.22720.50890.42000.067*
C130.31522 (12)0.4946 (2)0.38997 (12)0.0480 (6)
H13A0.32650.43120.42050.058*
C140.35750 (10)0.5414 (2)0.34532 (11)0.0369 (5)
H14A0.39780.50900.34550.044*
C150.26167 (11)0.7842 (2)0.25435 (13)0.0495 (6)
H15A0.23180.83460.27810.074*
H15B0.24270.74960.21330.074*
H15C0.29670.83450.24170.074*
C160.40878 (9)0.87239 (19)0.36281 (10)0.0276 (4)
C170.37778 (10)0.9723 (2)0.33442 (11)0.0353 (5)
C180.32210 (11)1.0061 (2)0.36232 (12)0.0470 (6)
H18A0.30051.07310.34300.056*
C190.29730 (11)0.9465 (2)0.41646 (13)0.0481 (7)
H19A0.25920.97220.43410.058*
C200.32791 (10)0.8488 (2)0.44523 (12)0.0389 (5)
H20A0.31120.80680.48280.047*
C210.38290 (9)0.8131 (2)0.41877 (10)0.0311 (5)
H21A0.40400.74630.43890.037*
C220.40310 (13)1.0441 (2)0.27621 (13)0.0538 (7)
H22A0.37411.10830.26310.081*
H22B0.40970.98970.23750.081*
H22C0.44201.08120.29010.081*
C230.52007 (8)0.78697 (18)0.41210 (9)0.0244 (4)
C240.55118 (9)0.87983 (19)0.44804 (10)0.0307 (5)
C250.57354 (11)0.8554 (2)0.51278 (11)0.0395 (6)
H25A0.59390.91820.53740.047*
C260.56695 (11)0.7426 (2)0.54230 (11)0.0410 (6)
H26A0.58220.72840.58700.049*
C270.53823 (10)0.6504 (2)0.50693 (11)0.0385 (5)
H27A0.53430.57180.52670.046*
C280.51505 (9)0.67275 (19)0.44232 (10)0.0308 (5)
H28A0.49530.60870.41810.037*
C290.56121 (12)1.0050 (2)0.41859 (12)0.0467 (6)
H29A0.58031.05760.45300.070*
H29B0.52181.03990.40440.070*
H29C0.58800.99890.37920.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0244 (3)0.0252 (3)0.0273 (3)0.0011 (2)0.0027 (2)0.0013 (2)
P20.0255 (3)0.0219 (3)0.0236 (3)0.0003 (2)0.0008 (2)0.0012 (2)
C10.0225 (10)0.0212 (10)0.0230 (9)0.0001 (8)0.0004 (8)0.0001 (8)
C20.0265 (10)0.0289 (11)0.0286 (11)0.0079 (9)0.0040 (8)0.0023 (9)
C30.0264 (11)0.0381 (12)0.0279 (11)0.0111 (9)0.0049 (8)0.0030 (9)
C40.0375 (13)0.0503 (15)0.0325 (12)0.0131 (11)0.0014 (10)0.0090 (11)
C50.0476 (14)0.0360 (14)0.0467 (14)0.0114 (11)0.0092 (11)0.0157 (11)
C60.0487 (14)0.0270 (12)0.0486 (14)0.0040 (11)0.0087 (11)0.0049 (11)
C70.0402 (13)0.0300 (12)0.0335 (12)0.0061 (10)0.0035 (9)0.0025 (9)
C80.0323 (12)0.0480 (14)0.0325 (11)0.0062 (11)0.0042 (9)0.0013 (10)
C90.0270 (11)0.0340 (12)0.0305 (11)0.0058 (9)0.0004 (9)0.0101 (9)
C100.0279 (11)0.0482 (15)0.0393 (12)0.0022 (10)0.0013 (9)0.0190 (11)
C110.0289 (12)0.077 (2)0.0488 (15)0.0046 (13)0.0070 (11)0.0227 (15)
C120.0441 (15)0.078 (2)0.0463 (15)0.0204 (15)0.0180 (12)0.0119 (15)
C130.0509 (15)0.0532 (16)0.0401 (13)0.0119 (13)0.0099 (11)0.0006 (12)
C140.0344 (12)0.0395 (13)0.0368 (12)0.0050 (10)0.0058 (10)0.0041 (10)
C150.0350 (13)0.0583 (17)0.0550 (15)0.0100 (12)0.0064 (11)0.0154 (13)
C160.0265 (10)0.0278 (11)0.0283 (10)0.0020 (9)0.0047 (8)0.0078 (9)
C170.0386 (12)0.0362 (13)0.0310 (11)0.0101 (10)0.0051 (9)0.0064 (10)
C180.0418 (14)0.0529 (16)0.0460 (14)0.0241 (12)0.0066 (11)0.0060 (12)
C190.0307 (13)0.0646 (18)0.0491 (15)0.0133 (12)0.0015 (11)0.0127 (13)
C200.0297 (12)0.0483 (15)0.0387 (12)0.0013 (11)0.0036 (10)0.0087 (11)
C210.0284 (11)0.0323 (12)0.0325 (11)0.0027 (9)0.0001 (9)0.0067 (9)
C220.0684 (18)0.0474 (16)0.0456 (15)0.0237 (14)0.0029 (13)0.0111 (12)
C230.0215 (10)0.0274 (11)0.0244 (10)0.0041 (8)0.0018 (8)0.0011 (8)
C240.0315 (11)0.0307 (12)0.0299 (11)0.0024 (9)0.0028 (9)0.0066 (9)
C250.0444 (14)0.0397 (14)0.0343 (12)0.0005 (11)0.0072 (10)0.0090 (11)
C260.0458 (14)0.0513 (15)0.0258 (11)0.0071 (12)0.0086 (10)0.0026 (11)
C270.0453 (13)0.0378 (13)0.0324 (12)0.0023 (11)0.0007 (10)0.0067 (10)
C280.0327 (11)0.0311 (12)0.0284 (10)0.0019 (9)0.0011 (9)0.0011 (9)
C290.0640 (16)0.0334 (13)0.0422 (14)0.0106 (12)0.0127 (12)0.0073 (11)
Geometric parameters (Å, º) top
P1—C21.855 (2)C14—H14A0.9500
P1—C91.857 (2)C15—H15A0.9800
P1—C11.8824 (19)C15—H15B0.9800
P2—C231.8401 (19)C15—H15C0.9800
P2—C161.854 (2)C16—C171.402 (3)
P2—C11.8991 (19)C16—C211.405 (3)
C1—C1i1.582 (4)C17—C181.394 (3)
C1—H1A1.0000C17—C221.502 (3)
C2—C71.395 (3)C18—C191.369 (3)
C2—C31.404 (3)C18—H18A0.9500
C3—C41.396 (3)C19—C201.381 (3)
C3—C81.504 (3)C19—H19A0.9500
C4—C51.377 (3)C20—C211.375 (3)
C4—H4A0.9500C20—H20A0.9500
C5—C61.375 (3)C21—H21A0.9500
C5—H5A0.9500C22—H22A0.9800
C6—C71.387 (3)C22—H22B0.9800
C6—H6A0.9500C22—H22C0.9800
C7—H7A0.9500C23—C281.392 (3)
C8—H8A0.9800C23—C241.410 (3)
C8—H8B0.9800C24—C251.385 (3)
C8—H8C0.9800C24—C291.508 (3)
C9—C141.394 (3)C25—C261.376 (3)
C9—C101.410 (3)C25—H25A0.9500
C10—C111.400 (3)C26—C271.375 (3)
C10—C151.501 (3)C26—H26A0.9500
C11—C121.374 (4)C27—C281.385 (3)
C11—H11A0.9500C27—H27A0.9500
C12—C131.377 (4)C28—H28A0.9500
C12—H12A0.9500C29—H29A0.9800
C13—C141.383 (3)C29—H29B0.9800
C13—H13A0.9500C29—H29C0.9800
C2—P1—C996.72 (9)C10—C15—H15A109.5
C2—P1—C1102.67 (9)C10—C15—H15B109.5
C9—P1—C1105.95 (9)H15A—C15—H15B109.5
C23—P2—C1697.29 (9)C10—C15—H15C109.5
C23—P2—C1107.04 (9)H15A—C15—H15C109.5
C16—P2—C1106.12 (8)H15B—C15—H15C109.5
C1i—C1—P1108.72 (16)C17—C16—C21118.48 (19)
C1i—C1—P2107.29 (9)C17—C16—P2118.84 (16)
P1—C1—P2109.69 (9)C21—C16—P2122.44 (15)
C1i—C1—H1A110.4C18—C17—C16118.2 (2)
P1—C1—H1A110.4C18—C17—C22119.7 (2)
P2—C1—H1A110.4C16—C17—C22122.2 (2)
C7—C2—C3118.62 (19)C19—C18—C17122.5 (2)
C7—C2—P1122.33 (15)C19—C18—H18A118.7
C3—C2—P1119.05 (16)C17—C18—H18A118.7
C4—C3—C2118.4 (2)C18—C19—C20119.7 (2)
C4—C3—C8119.20 (19)C18—C19—H19A120.2
C2—C3—C8122.41 (19)C20—C19—H19A120.2
C5—C4—C3122.0 (2)C21—C20—C19119.2 (2)
C5—C4—H4A119.0C21—C20—H20A120.4
C3—C4—H4A119.0C19—C20—H20A120.4
C6—C5—C4119.9 (2)C20—C21—C16121.9 (2)
C6—C5—H5A120.1C20—C21—H21A119.0
C4—C5—H5A120.1C16—C21—H21A119.0
C5—C6—C7119.1 (2)C17—C22—H22A109.5
C5—C6—H6A120.4C17—C22—H22B109.5
C7—C6—H6A120.4H22A—C22—H22B109.5
C6—C7—C2122.0 (2)C17—C22—H22C109.5
C6—C7—H7A119.0H22A—C22—H22C109.5
C2—C7—H7A119.0H22B—C22—H22C109.5
C3—C8—H8A109.5C28—C23—C24118.42 (18)
C3—C8—H8B109.5C28—C23—P2125.72 (15)
H8A—C8—H8B109.5C24—C23—P2115.75 (15)
C3—C8—H8C109.5C25—C24—C23119.0 (2)
H8A—C8—H8C109.5C25—C24—C29118.57 (19)
H8B—C8—H8C109.5C23—C24—C29122.45 (18)
C14—C9—C10118.9 (2)C26—C25—C24121.6 (2)
C14—C9—P1121.96 (16)C26—C25—H25A119.2
C10—C9—P1118.96 (17)C24—C25—H25A119.2
C11—C10—C9117.9 (2)C27—C26—C25119.8 (2)
C11—C10—C15118.3 (2)C27—C26—H26A120.1
C9—C10—C15123.8 (2)C25—C26—H26A120.1
C12—C11—C10122.3 (2)C26—C27—C28119.6 (2)
C12—C11—H11A118.8C26—C27—H27A120.2
C10—C11—H11A118.8C28—C27—H27A120.2
C11—C12—C13119.6 (2)C27—C28—C23121.5 (2)
C11—C12—H12A120.2C27—C28—H28A119.3
C13—C12—H12A120.2C23—C28—H28A119.3
C12—C13—C14119.5 (3)C24—C29—H29A109.5
C12—C13—H13A120.2C24—C29—H29B109.5
C14—C13—H13A120.2H29A—C29—H29B109.5
C13—C14—C9121.7 (2)C24—C29—H29C109.5
C13—C14—H14A119.1H29A—C29—H29C109.5
C9—C14—H14A119.1H29B—C29—H29C109.5
C2—P1—C1—C1i59.35 (7)C11—C12—C13—C140.6 (4)
C9—P1—C1—C1i160.24 (7)C12—C13—C14—C90.2 (4)
C2—P1—C1—P2176.38 (9)C10—C9—C14—C130.3 (3)
C9—P1—C1—P282.73 (11)P1—C9—C14—C13175.23 (18)
C23—P2—C1—C1i105.45 (15)C23—P2—C16—C17142.76 (16)
C16—P2—C1—C1i151.44 (14)C1—P2—C16—C17107.09 (16)
C23—P2—C1—P1136.62 (9)C23—P2—C16—C2131.53 (18)
C16—P2—C1—P133.51 (12)C1—P2—C16—C2178.62 (18)
C9—P1—C2—C773.92 (18)C21—C16—C17—C181.4 (3)
C1—P1—C2—C734.14 (19)P2—C16—C17—C18175.89 (17)
C9—P1—C2—C3105.52 (16)C21—C16—C17—C22177.7 (2)
C1—P1—C2—C3146.42 (15)P2—C16—C17—C223.2 (3)
C7—C2—C3—C42.1 (3)C16—C17—C18—C190.8 (4)
P1—C2—C3—C4178.47 (15)C22—C17—C18—C19178.3 (2)
C7—C2—C3—C8178.14 (19)C17—C18—C19—C200.1 (4)
P1—C2—C3—C81.3 (3)C18—C19—C20—C210.1 (4)
C2—C3—C4—C50.5 (3)C19—C20—C21—C160.6 (3)
C8—C3—C4—C5179.7 (2)C17—C16—C21—C201.3 (3)
C3—C4—C5—C61.2 (3)P2—C16—C21—C20175.60 (17)
C4—C5—C6—C71.1 (3)C16—P2—C23—C2883.90 (18)
C5—C6—C7—C20.5 (3)C1—P2—C23—C2825.49 (19)
C3—C2—C7—C62.2 (3)C16—P2—C23—C2492.16 (16)
P1—C2—C7—C6178.40 (16)C1—P2—C23—C24158.45 (15)
C2—P1—C9—C1467.02 (18)C28—C23—C24—C252.3 (3)
C1—P1—C9—C1438.25 (19)P2—C23—C24—C25174.03 (16)
C2—P1—C9—C10108.55 (17)C28—C23—C24—C29177.5 (2)
C1—P1—C9—C10146.18 (16)P2—C23—C24—C296.1 (3)
C14—C9—C10—C110.4 (3)C23—C24—C25—C261.0 (3)
P1—C9—C10—C11175.27 (16)C29—C24—C25—C26178.9 (2)
C14—C9—C10—C15179.4 (2)C24—C25—C26—C270.8 (4)
P1—C9—C10—C154.9 (3)C25—C26—C27—C281.3 (3)
C9—C10—C11—C120.0 (3)C26—C27—C28—C230.1 (3)
C15—C10—C11—C12179.8 (2)C24—C23—C28—C271.9 (3)
C10—C11—C12—C130.5 (4)P2—C23—C28—C27174.07 (16)
Symmetry code: (i) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC58H58P4
Mr878.92
Crystal system, space groupMonoclinic, C2/c
Temperature (K)193
a, b, c (Å)21.8875 (11), 10.9702 (6), 19.691 (1)
β (°) 90.761 (3)
V3)4727.6 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.42 × 0.40 × 0.24
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.942, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
19717, 4345, 3343
Rint0.049
(sin θ/λ)max1)0.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.102, 1.01
No. of reflections4345
No. of parameters284
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.35, 0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2005), XPREP (Bruker, 2005) and SADABS (Bruker, 2007), SHELXTL (Sheldrick, 2008), SHELXTL (Bruker, 2005) and CrystalMaker (CrystalMaker, 1994), XCIF (Bruker, 2005).

 

Acknowledgements

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).

References

First citationBraunstein, P., Hasselbring, R., DeCian, A. & Fischer, J. (1995a). Bull. Soc. Chim. Fr. 132, 691-695.  CAS
First citationBraunstein, P., Hasselbring, R., Tiripicchio, A. & Ugozzoli, F. (1995b). J. Chem. Soc. Chem. Commun. pp. 37–38.  CrossRef Web of Science
First citationBruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2007). SADABS and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCrystalMaker (1994). CrystalMaker. CrystalMaker Software Ltd, Oxford, England. URL: www.CrystalMaker.com.
First citationSchmidbaur, H. & Deschler, U. (1983). Chem. Ber. 116, 1386–1392.  CrossRef CAS Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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