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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4,6-Bis(di­phenyl­phosphan­yl)dibenzo[b,d]furan

aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
*Correspondence e-mail: bala@ukzn.ac.za

(Received 4 November 2011; accepted 10 November 2011; online 16 November 2011)

The asymmetric unit of the title compound, C36H26OP2, comprises two mol­ecules which have slightly different conformations of the phenyl ring substituents. In both mol­ecules, the dibenzofuran unit is close to being planar, with dihedral angles of 3.20 (3) and 1.86 (2)° for the two mol­ecules. Its planarity affects the intra­molecular distances between P atoms, with P⋯P distances of 5.574 (2) and 5.485 (2) Å for the two mol­ecules.

Related literature

For related syntheses, see: Kranenburg et al. (1995[Kranenburg, M., Vanderburgt, Y. E. M., Kamer, P. C. J., van Leeuwen, P. W. N. M., Goubitz, K. & Fraanje, J. (1995). Organometallics, 14, 3081-3089.]); Hillebrand et al. (1995[Hillebrand, S., Bruckmann, J., Kruger, C. & Haenel, M. W. (1995). Tetrahedron Lett. 36, 75-78.]). For related structures, see: Vogl et al. (1996[Vogl, E. M., Bruckmann, J., Krüger, C. & Haenel, M. W. (1996). J. Organomet. Chem. 520, 249-252.]); Marimuthu et al. (2008a[Marimuthu, T., Bala, M. D. & Friedrich, H. B. (2008a). Acta Cryst. E64, o711.],b[Marimuthu, T., Bala, M. D. & Friedrich, H. B. (2008b). Acta Cryst. E64, o772.]). For structures containing the dibenzofuran unit, see: Dideberg et al. (1972[Dideberg, O., Dupont, L. & André, J. M. (1972). Acta Cryst. B28, 1002-1007.]); Banerjee (1973[Banerjee, A. (1973). Acta Cryst. B29, 2070-2074.]); Reppart et al., (1984[Reppart, W. J., Gallucci, J. C., Lundstedt, A. P. & Gerkin, R. E. (1984). Acta Cryst. C40, 1572-1576.]).

[Scheme 1]

Experimental

Crystal data
  • C36H26OP2

  • Mr = 536.51

  • Triclinic, [P \overline 1]

  • a = 11.7463 (2) Å

  • b = 14.7238 (3) Å

  • c = 16.7140 (4) Å

  • α = 96.821 (2)°

  • β = 96.351 (5)°

  • γ = 95.240 (2)°

  • V = 2836.58 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 173 K

  • 0.40 × 0.22 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 28406 measured reflections

  • 12364 independent reflections

  • 8323 reflections with I > 2σ(I)

  • Rint = 0.052

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.100

  • S = 0.90

  • 12363 reflections

  • 703 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2005[Bruker (2005). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The crystal structure of (I)comprises the two crystallographically independent conformers of the title compound (I)(Fig. 1). The dibenzofuran or aromatic ether backbone has been selectively functionalised with diphosphane donors. The diphosphane ligand has been used in Rh hydroformylation catalysis (Kranenburg et al., 1995). In a study towards the isolation of stable coordination complexes, the complex of Co with a ligand (I) was published (Vogl et al. 1996); herein we report a different conformation of the ligand to the reported one. The individual five and six membered rings of dibenzofuran moiety in (I) are planar, but not coplanar; dihedral angles of 1.32° & 1.88° (molecule A) and 1.52° & 0.42° (molecule B) are observed. The planarity of the dibenzofuran moiety has been a subject of interest reporting the dihedral angles of 1.12° (Dideberg et al., 1972), 1.1° (Banerjee, 1973) and 1.5° (Reppart et al., 1984). However, (Vogl et al. 1996) have reported a larger dihedral angle of 2.45° and 2.51° which is attributed to the difference in the disposition of the phenyl rings as compared to previous reports and the title compound.

In a chelating diphosphane compound, the magnitude of the intramolecular separation distances between P atoms has a big impact on the stability of its coordination compounds. In the title compound, the rigid backbone pushes the diphosphane pincers apart resulting in relatively large intramolecular separation distances between the P atoms of 5.574 (2) and 5.485 (2) for molecules A and B, respectively. This value is slightly smaller than the 5.741 (1) reported by (Vogl et al. 1996), but notably larger than in xantphos, [4.025 (2) (Kranenburg et al., 1995) and 4.046 Å (Hillebrand et al. 1995)] and nixantphos, 4.255 (2) Å (Marimuthu et al. 2008a).

Related literature top

For related syntheses, see: Kranenburg et al. (1995); Hillebrand et al. (1995). For related structures, see: Vogl et al. (1996); Marimuthu et al. (2008a,b). For structures containing the dibenzofuran unit, see: Dideberg et al. (1972); Banerjee (1973); Reppart et al., (1984).

Experimental top

The preparation of (I) was adapted from literature (Kranenburg et al., 1995). A solution of dibenzofuran (1.5 g, 8.9 mmol) in 60 mL of dry ether was cooled to 208 K, using a dry ice/acetone bath. Thereafter, tetramethylethylenediamine (3.8 mL, 25 mmol) was added and the solution stirred. Under a positive pressure of argon, nBuLi (15.6 mL, 25 mmol) was added dropwise and the reaction left to stir for a further 16 h. Thereafter, the stirred reaction mixture was cooled to 208 K and chlorodiphenylphosphane (4.6 mL, 25 mmol) in hexane (13 mL) added dropwise. Then, the reaction was left to stir overnight. A (1/1) mixture of dichloromethane (DCM)/water (25 mL) was added. After allowing sufficient time to stir, the organic layer was removed, and the aqueous layer extracted with DCM (2 x 15 mL). The combined organic fractions were dried over anhydrous MgSO4, filtered, and the solvent evacuated to dryness. The resulting oil was washed with hexane and recrystalised from DCM/EtOH (1:1) to afford colourless crystals of (I) suitable for X-ray analysis. [yield: 3.4 g, 71%; m.p. 485 K]. Spectroscopic analysis: 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 7.91 (dd, J = 7.7, 1.2 Hz, 2H), 7.44 – 7.09 (m, P(C6H5)2 and H xanthene, 22H), 7.03 (td, J(H,H) = 7.4, J(P,H) 1.2 Hz, 2H); 13C NMR (101 MHz, CDCl3, δ, p.p.m.): 157.9 (d, J(P,C) = 13.7 Hz, CO), 135.8 (d, J(P,C) = 10.7 Hz, phenyl C-ipso, PC), 133.8 (d, J(P,C) = 20.3 Hz, CH), 132.0 (d, J = 8.6 Hz, CH), 128.7 (s, CH), 128.3 (d, J (P,C) = 7.1 Hz, CH), 123.5 (bs, C), 123.1 (d, J(P,C) = 3.0 Hz, CH), 121.2 (d, J (P,C) = 19.5 Hz, C), 121.5 (CH); 31P NMR (243 MHz, CDCl3 δ, p.p.m.): -16.9; IR (neat, νmax, cm-1): 3046 (w), 3006 (w), 1476 (m), 1433 (s), 1408 (s), 1387 (m), 1173 (s), 772 (m), 739 (s), 691 (s); HR—MS (ESI) (m/z): 537.1531 [M + H]+ calcd. for C36H27OP2, 537.1532.

Refinement top

All H-atoms were refined using a riding model, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C).

Structure description top

The crystal structure of (I)comprises the two crystallographically independent conformers of the title compound (I)(Fig. 1). The dibenzofuran or aromatic ether backbone has been selectively functionalised with diphosphane donors. The diphosphane ligand has been used in Rh hydroformylation catalysis (Kranenburg et al., 1995). In a study towards the isolation of stable coordination complexes, the complex of Co with a ligand (I) was published (Vogl et al. 1996); herein we report a different conformation of the ligand to the reported one. The individual five and six membered rings of dibenzofuran moiety in (I) are planar, but not coplanar; dihedral angles of 1.32° & 1.88° (molecule A) and 1.52° & 0.42° (molecule B) are observed. The planarity of the dibenzofuran moiety has been a subject of interest reporting the dihedral angles of 1.12° (Dideberg et al., 1972), 1.1° (Banerjee, 1973) and 1.5° (Reppart et al., 1984). However, (Vogl et al. 1996) have reported a larger dihedral angle of 2.45° and 2.51° which is attributed to the difference in the disposition of the phenyl rings as compared to previous reports and the title compound.

In a chelating diphosphane compound, the magnitude of the intramolecular separation distances between P atoms has a big impact on the stability of its coordination compounds. In the title compound, the rigid backbone pushes the diphosphane pincers apart resulting in relatively large intramolecular separation distances between the P atoms of 5.574 (2) and 5.485 (2) for molecules A and B, respectively. This value is slightly smaller than the 5.741 (1) reported by (Vogl et al. 1996), but notably larger than in xantphos, [4.025 (2) (Kranenburg et al., 1995) and 4.046 Å (Hillebrand et al. 1995)] and nixantphos, 4.255 (2) Å (Marimuthu et al. 2008a).

For related syntheses, see: Kranenburg et al. (1995); Hillebrand et al. (1995). For related structures, see: Vogl et al. (1996); Marimuthu et al. (2008a,b). For structures containing the dibenzofuran unit, see: Dideberg et al. (1972); Banerjee (1973); Reppart et al., (1984).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of compound (I). Displacement ellipsoids are represented at the 50% probability level. Hydrogen atoms omitted for clarity.
4,6-Bis(diphenylphosphanyl)dibenzo[b,d]furan top
Crystal data top
C36H26OP2Z = 4
Mr = 536.51F(000) = 1120
Triclinic, P1Dx = 1.256 Mg m3
Hall symbol: -P 1Melting point: 485 K
a = 11.7463 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.7238 (3) ÅCell parameters from 7048 reflections
c = 16.7140 (4) Åθ = 2.3–26.9°
α = 96.821 (2)°µ = 0.18 mm1
β = 96.351 (5)°T = 173 K
γ = 95.240 (2)°Prism, colourless
V = 2836.58 (10) Å30.40 × 0.22 × 0.18 mm
Data collection top
Bruker APEXII CCD
diffractometer
8323 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
Graphite monochromatorθmax = 27.0°, θmin = 1.2°
φ and ω scansh = 1514
28406 measured reflectionsk = 1418
12364 independent reflectionsl = 2119
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 0.90 w = 1/[σ2(Fo2) + (0.0468P)2]
where P = (Fo2 + 2Fc2)/3
12363 reflections(Δ/σ)max = 0.002
703 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C36H26OP2γ = 95.240 (2)°
Mr = 536.51V = 2836.58 (10) Å3
Triclinic, P1Z = 4
a = 11.7463 (2) ÅMo Kα radiation
b = 14.7238 (3) ŵ = 0.18 mm1
c = 16.7140 (4) ÅT = 173 K
α = 96.821 (2)°0.40 × 0.22 × 0.18 mm
β = 96.351 (5)°
Data collection top
Bruker APEXII CCD
diffractometer
8323 reflections with I > 2σ(I)
28406 measured reflectionsRint = 0.052
12364 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 0.90Δρmax = 0.29 e Å3
12363 reflectionsΔρmin = 0.30 e Å3
703 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. 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.

One reflection was an outlier.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.37941 (15)0.82094 (11)0.53677 (10)0.0274 (4)
C2A0.31908 (16)0.88254 (12)0.49585 (11)0.0332 (4)
H2A0.30660.87300.43820.040*
C3A0.27640 (17)0.95794 (12)0.53724 (12)0.0370 (5)
H3A0.23570.99810.50710.044*
C4A0.29204 (16)0.97513 (12)0.62065 (12)0.0335 (4)
H4A0.26251.02640.64820.040*
C5A0.35234 (16)0.91537 (11)0.66360 (11)0.0285 (4)
C6A0.39397 (15)0.84093 (11)0.62080 (11)0.0268 (4)
C7A0.48344 (15)0.79506 (11)0.82089 (11)0.0282 (4)
C8A0.46446 (16)0.84741 (12)0.89246 (11)0.0333 (4)
H8A0.49010.82770.94290.040*
C9A0.40934 (17)0.92762 (13)0.89305 (12)0.0373 (5)
H9A0.40020.96140.94360.045*
C10A0.36791 (17)0.95880 (12)0.82206 (11)0.0340 (5)
H10A0.32931.01280.82280.041*
C11A0.38466 (15)0.90833 (11)0.74890 (11)0.0284 (4)
C12A0.44181 (15)0.82992 (11)0.75056 (10)0.0270 (4)
C21A0.33887 (16)0.62567 (11)0.49008 (10)0.0291 (4)
C22A0.23537 (17)0.63032 (13)0.52293 (11)0.0366 (5)
H22A0.21250.68850.54170.044*
C23A0.16524 (19)0.55069 (14)0.52854 (12)0.0440 (5)
H23A0.09550.55470.55200.053*
C24A0.1962 (2)0.46631 (13)0.50037 (12)0.0431 (5)
H24A0.14770.41210.50410.052*
C25A0.2978 (2)0.45991 (13)0.46652 (12)0.0438 (5)
H25A0.31890.40150.44630.053*
C26A0.36865 (18)0.53926 (12)0.46226 (12)0.0378 (5)
H26A0.43910.53460.43990.045*
C31A0.42922 (15)0.74431 (11)0.38134 (10)0.0278 (4)
C32A0.35837 (16)0.68820 (12)0.31898 (11)0.0317 (4)
H32A0.30690.63990.33160.038*
C33A0.36212 (17)0.70197 (13)0.23882 (12)0.0375 (5)
H33A0.31410.66240.19700.045*
C34A0.43455 (17)0.77238 (13)0.21902 (12)0.0386 (5)
H34A0.43690.78140.16390.046*
C35A0.50414 (18)0.83009 (13)0.28039 (12)0.0404 (5)
H35A0.55330.87970.26740.048*
C36A0.50225 (17)0.81565 (12)0.36026 (11)0.0351 (5)
H36A0.55140.85490.40170.042*
C41A0.58347 (16)0.67629 (11)0.92241 (11)0.0302 (4)
C42A0.68812 (17)0.71181 (12)0.96745 (12)0.0360 (5)
H42A0.74590.74220.94160.043*
C43A0.7095 (2)0.70373 (14)1.04910 (13)0.0472 (6)
H43A0.78120.72911.07890.057*
C44A0.6276 (2)0.65914 (14)1.08731 (13)0.0518 (6)
H44A0.64240.65361.14350.062*
C45A0.5234 (2)0.62240 (14)1.04374 (13)0.0530 (6)
H45A0.46680.59121.06990.064*
C46A0.50146 (19)0.63084 (13)0.96218 (12)0.0442 (5)
H46A0.42950.60530.93280.053*
C51A0.44897 (15)0.60216 (11)0.77260 (10)0.0265 (4)
C52A0.33230 (16)0.61084 (12)0.77160 (11)0.0357 (5)
H52A0.30820.66760.79320.043*
C53A0.25030 (17)0.53820 (12)0.73967 (11)0.0376 (5)
H53A0.17070.54540.73920.045*
C54A0.28428 (18)0.45581 (13)0.70864 (11)0.0378 (5)
H54A0.22820.40590.68670.045*
C55A0.39956 (19)0.44551 (13)0.70934 (13)0.0466 (6)
H55A0.42300.38830.68840.056*
C56A0.48183 (17)0.51863 (13)0.74064 (12)0.0398 (5)
H56A0.56130.51130.74010.048*
O1A0.44942 (10)0.78761 (7)0.67250 (7)0.0282 (3)
P1A0.44520 (4)0.72421 (3)0.48805 (3)0.02816 (12)
P2A0.56344 (4)0.69353 (3)0.81530 (3)0.02891 (12)
C1B0.00064 (16)0.29822 (12)0.74027 (11)0.0290 (4)
C2B0.01889 (16)0.35240 (12)0.67774 (11)0.0338 (4)
H2B0.00260.33240.62590.041*
C3B0.06894 (17)0.43487 (12)0.68878 (11)0.0355 (5)
H3B0.07950.46970.64470.043*
C4B0.10324 (16)0.46657 (12)0.76244 (11)0.0326 (4)
H4B0.13800.52230.76940.039*
C5B0.08556 (15)0.41471 (11)0.82632 (11)0.0280 (4)
C6B0.03372 (15)0.33400 (11)0.81348 (10)0.0269 (4)
C7B0.07776 (15)0.32607 (11)1.01918 (10)0.0257 (4)
C8B0.12956 (16)0.39021 (11)1.06783 (11)0.0307 (4)
H8B0.13660.38101.12250.037*
C9B0.17122 (17)0.46730 (12)1.03859 (12)0.0354 (5)
H9B0.20630.50891.07370.043*
C10B0.16281 (16)0.48458 (12)0.96022 (11)0.0335 (4)
H10B0.19140.53730.94100.040*
C11B0.11105 (16)0.42244 (11)0.90970 (11)0.0277 (4)
C12B0.07107 (15)0.34590 (11)0.94068 (10)0.0258 (4)
C21B0.04604 (17)0.10425 (12)0.73400 (10)0.0297 (4)
C22B0.16215 (17)0.11507 (13)0.71759 (11)0.0369 (5)
H22B0.18420.17390.70860.044*
C23B0.24634 (19)0.04216 (13)0.71404 (12)0.0423 (5)
H23B0.32520.05090.70210.051*
C24B0.2155 (2)0.04334 (13)0.72784 (12)0.0450 (6)
H24B0.27300.09360.72560.054*
C25B0.1012 (2)0.05521 (14)0.74479 (13)0.0513 (6)
H25B0.07970.11400.75430.062*
C26B0.01721 (19)0.01758 (13)0.74821 (12)0.0422 (5)
H26B0.06150.00830.76050.051*
C31B0.09720 (16)0.17990 (12)0.62744 (11)0.0307 (4)
C32B0.01672 (18)0.13673 (13)0.56366 (11)0.0403 (5)
H32B0.05580.11040.57470.048*
C33B0.04143 (19)0.13184 (14)0.48452 (12)0.0455 (5)
H33B0.01410.10190.44160.055*
C34B0.14588 (19)0.17008 (13)0.46724 (12)0.0420 (5)
H34B0.16200.16740.41260.050*
C35B0.22697 (18)0.21236 (13)0.52976 (13)0.0402 (5)
H35B0.29930.23860.51820.048*
C36B0.20306 (17)0.21651 (12)0.60921 (12)0.0348 (5)
H36B0.25990.24480.65200.042*
C41B0.01766 (15)0.24706 (10)1.16214 (10)0.0247 (4)
C42B0.08149 (16)0.28867 (11)1.21114 (11)0.0301 (4)
H42B0.14890.30441.18700.036*
C43B0.08319 (17)0.30748 (12)1.29468 (11)0.0343 (5)
H43B0.15100.33681.32730.041*
C44B0.01381 (18)0.28352 (12)1.33004 (11)0.0350 (5)
H44B0.01300.29661.38720.042*
C45B0.11229 (17)0.24048 (12)1.28261 (11)0.0363 (5)
H45B0.17870.22331.30730.044*
C46B0.11418 (16)0.22246 (12)1.19921 (11)0.0315 (4)
H46B0.18220.19301.16700.038*
C51B0.11728 (16)0.13006 (11)1.01669 (10)0.0279 (4)
C52B0.20495 (17)0.13010 (13)0.95380 (11)0.0387 (5)
H52B0.21840.18570.93250.046*
C53B0.27329 (19)0.04889 (15)0.92185 (12)0.0477 (6)
H53B0.33280.04930.87850.057*
C54B0.25549 (19)0.03169 (14)0.95239 (14)0.0479 (6)
H54B0.30210.08700.93000.058*
C55B0.16983 (19)0.03237 (13)1.01565 (14)0.0454 (6)
H55B0.15820.08791.03760.055*
C56B0.10075 (17)0.04794 (12)1.04714 (12)0.0361 (5)
H56B0.04110.04681.09020.043*
O1B0.02303 (10)0.29065 (7)0.88294 (7)0.0272 (3)
P1B0.07320 (4)0.19318 (3)0.73453 (3)0.03273 (12)
P2B0.00896 (4)0.22826 (3)1.05283 (3)0.02579 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0267 (10)0.0243 (9)0.0301 (10)0.0013 (7)0.0008 (8)0.0037 (7)
C2A0.0340 (11)0.0309 (10)0.0334 (11)0.0027 (8)0.0024 (9)0.0052 (8)
C3A0.0363 (12)0.0289 (10)0.0453 (13)0.0059 (8)0.0043 (9)0.0089 (9)
C4A0.0326 (11)0.0233 (9)0.0434 (12)0.0034 (8)0.0029 (9)0.0017 (8)
C5A0.0284 (10)0.0216 (9)0.0348 (11)0.0011 (7)0.0040 (8)0.0027 (7)
C6A0.0253 (10)0.0239 (9)0.0309 (10)0.0003 (7)0.0018 (8)0.0059 (7)
C7A0.0259 (10)0.0286 (10)0.0295 (10)0.0011 (7)0.0046 (8)0.0036 (8)
C8A0.0326 (11)0.0368 (11)0.0298 (11)0.0001 (8)0.0044 (8)0.0038 (8)
C9A0.0419 (13)0.0374 (11)0.0309 (11)0.0025 (9)0.0088 (9)0.0047 (9)
C10A0.0365 (12)0.0269 (10)0.0388 (12)0.0027 (8)0.0095 (9)0.0007 (8)
C11A0.0279 (10)0.0232 (9)0.0333 (10)0.0016 (7)0.0055 (8)0.0017 (7)
C12A0.0275 (10)0.0257 (9)0.0267 (10)0.0006 (7)0.0051 (8)0.0005 (7)
C21A0.0320 (11)0.0275 (10)0.0269 (10)0.0021 (8)0.0018 (8)0.0057 (7)
C22A0.0424 (13)0.0325 (11)0.0344 (11)0.0005 (9)0.0085 (9)0.0016 (8)
C23A0.0474 (14)0.0473 (13)0.0355 (12)0.0084 (10)0.0100 (10)0.0036 (9)
C24A0.0562 (15)0.0332 (11)0.0363 (12)0.0086 (10)0.0071 (10)0.0116 (9)
C25A0.0564 (15)0.0279 (11)0.0440 (13)0.0066 (10)0.0086 (11)0.0044 (9)
C26A0.0389 (12)0.0333 (11)0.0412 (12)0.0096 (9)0.0013 (9)0.0063 (9)
C31A0.0250 (10)0.0304 (10)0.0287 (10)0.0052 (7)0.0037 (8)0.0047 (8)
C32A0.0262 (10)0.0353 (10)0.0325 (11)0.0001 (8)0.0026 (8)0.0038 (8)
C33A0.0339 (12)0.0423 (12)0.0336 (11)0.0019 (9)0.0002 (9)0.0007 (9)
C34A0.0399 (13)0.0481 (12)0.0310 (11)0.0102 (9)0.0074 (9)0.0104 (9)
C35A0.0405 (13)0.0405 (12)0.0408 (12)0.0022 (9)0.0059 (10)0.0125 (9)
C36A0.0340 (12)0.0347 (11)0.0352 (11)0.0010 (8)0.0013 (9)0.0046 (8)
C41A0.0312 (11)0.0276 (10)0.0310 (10)0.0043 (8)0.0004 (8)0.0035 (8)
C42A0.0332 (12)0.0358 (11)0.0376 (12)0.0073 (8)0.0012 (9)0.0013 (9)
C43A0.0475 (14)0.0491 (13)0.0408 (13)0.0166 (10)0.0117 (11)0.0041 (10)
C44A0.0743 (18)0.0514 (14)0.0307 (12)0.0215 (12)0.0020 (12)0.0063 (10)
C45A0.0734 (18)0.0481 (13)0.0387 (13)0.0017 (12)0.0127 (12)0.0111 (10)
C46A0.0456 (14)0.0480 (13)0.0358 (12)0.0082 (10)0.0007 (10)0.0069 (9)
C51A0.0274 (10)0.0290 (9)0.0229 (9)0.0044 (8)0.0016 (8)0.0031 (7)
C52A0.0309 (11)0.0328 (10)0.0407 (12)0.0070 (8)0.0023 (9)0.0068 (8)
C53A0.0281 (11)0.0396 (11)0.0421 (12)0.0028 (8)0.0005 (9)0.0032 (9)
C54A0.0367 (12)0.0330 (11)0.0398 (12)0.0010 (9)0.0004 (9)0.0024 (9)
C55A0.0458 (14)0.0311 (11)0.0597 (15)0.0070 (9)0.0067 (11)0.0094 (10)
C56A0.0300 (11)0.0385 (11)0.0508 (13)0.0094 (9)0.0068 (9)0.0013 (9)
O1A0.0334 (7)0.0257 (6)0.0256 (7)0.0053 (5)0.0030 (5)0.0028 (5)
P1A0.0277 (3)0.0285 (3)0.0279 (3)0.00275 (19)0.0020 (2)0.00360 (19)
P2A0.0252 (3)0.0323 (3)0.0292 (3)0.0020 (2)0.0033 (2)0.0044 (2)
C1B0.0288 (10)0.0293 (10)0.0274 (10)0.0002 (8)0.0008 (8)0.0030 (7)
C2B0.0347 (12)0.0373 (11)0.0280 (10)0.0010 (9)0.0013 (8)0.0052 (8)
C3B0.0409 (12)0.0313 (10)0.0342 (11)0.0014 (9)0.0019 (9)0.0144 (8)
C4B0.0360 (12)0.0228 (9)0.0378 (11)0.0007 (8)0.0006 (9)0.0070 (8)
C5B0.0292 (10)0.0219 (9)0.0313 (10)0.0022 (7)0.0003 (8)0.0041 (7)
C6B0.0282 (10)0.0258 (9)0.0258 (10)0.0018 (7)0.0007 (8)0.0066 (7)
C7B0.0282 (10)0.0208 (9)0.0278 (10)0.0007 (7)0.0045 (8)0.0021 (7)
C8B0.0343 (11)0.0276 (10)0.0304 (10)0.0038 (8)0.0061 (8)0.0024 (8)
C9B0.0390 (12)0.0287 (10)0.0392 (12)0.0084 (8)0.0093 (9)0.0007 (8)
C10B0.0369 (12)0.0226 (9)0.0403 (12)0.0053 (8)0.0007 (9)0.0042 (8)
C11B0.0299 (10)0.0202 (9)0.0317 (10)0.0013 (7)0.0007 (8)0.0038 (7)
C12B0.0251 (10)0.0213 (9)0.0297 (10)0.0011 (7)0.0030 (8)0.0002 (7)
C21B0.0398 (12)0.0309 (10)0.0210 (9)0.0118 (8)0.0053 (8)0.0061 (7)
C22B0.0424 (13)0.0302 (10)0.0420 (12)0.0123 (9)0.0090 (10)0.0113 (9)
C23B0.0431 (13)0.0413 (12)0.0443 (13)0.0068 (10)0.0103 (10)0.0067 (9)
C24B0.0648 (17)0.0334 (11)0.0374 (12)0.0007 (10)0.0123 (11)0.0048 (9)
C25B0.0769 (19)0.0294 (11)0.0506 (14)0.0166 (11)0.0066 (13)0.0112 (10)
C26B0.0516 (14)0.0396 (12)0.0384 (12)0.0216 (10)0.0027 (10)0.0074 (9)
C31B0.0325 (11)0.0307 (10)0.0298 (10)0.0086 (8)0.0030 (8)0.0038 (8)
C32B0.0354 (12)0.0540 (13)0.0304 (11)0.0028 (10)0.0040 (9)0.0069 (9)
C33B0.0507 (15)0.0538 (13)0.0306 (12)0.0023 (11)0.0021 (10)0.0044 (9)
C34B0.0535 (15)0.0456 (12)0.0343 (12)0.0189 (10)0.0169 (10)0.0141 (9)
C35B0.0363 (12)0.0365 (11)0.0542 (14)0.0099 (9)0.0176 (10)0.0158 (10)
C36B0.0340 (12)0.0281 (10)0.0427 (12)0.0065 (8)0.0036 (9)0.0045 (8)
C41B0.0297 (10)0.0182 (8)0.0269 (10)0.0054 (7)0.0034 (8)0.0030 (7)
C42B0.0334 (11)0.0240 (9)0.0322 (10)0.0024 (8)0.0037 (8)0.0053 (7)
C43B0.0405 (12)0.0261 (10)0.0328 (11)0.0017 (8)0.0049 (9)0.0025 (8)
C44B0.0481 (13)0.0315 (10)0.0254 (10)0.0087 (9)0.0023 (9)0.0027 (8)
C45B0.0355 (12)0.0401 (11)0.0349 (11)0.0065 (9)0.0098 (9)0.0048 (9)
C46B0.0279 (11)0.0344 (10)0.0313 (11)0.0025 (8)0.0027 (8)0.0025 (8)
C51B0.0312 (11)0.0264 (9)0.0260 (10)0.0012 (8)0.0101 (8)0.0013 (7)
C52B0.0429 (13)0.0396 (11)0.0317 (11)0.0064 (9)0.0039 (9)0.0053 (8)
C53B0.0458 (14)0.0568 (14)0.0339 (12)0.0146 (11)0.0044 (10)0.0056 (10)
C54B0.0477 (14)0.0359 (12)0.0550 (15)0.0118 (10)0.0212 (12)0.0163 (10)
C55B0.0470 (14)0.0234 (10)0.0676 (16)0.0029 (9)0.0217 (12)0.0004 (10)
C56B0.0372 (12)0.0291 (10)0.0429 (12)0.0054 (8)0.0111 (9)0.0012 (8)
O1B0.0333 (7)0.0243 (6)0.0245 (7)0.0057 (5)0.0038 (5)0.0034 (5)
P1B0.0339 (3)0.0384 (3)0.0262 (3)0.0103 (2)0.0005 (2)0.0032 (2)
P2B0.0272 (3)0.0238 (2)0.0267 (3)0.00263 (19)0.0049 (2)0.00286 (18)
Geometric parameters (Å, º) top
C1A—C6A1.388 (2)C1B—C6B1.390 (2)
C1A—C2A1.396 (2)C1B—C2B1.400 (2)
C1A—P1A1.8312 (18)C1B—P1B1.8306 (19)
C2A—C3A1.399 (3)C2B—C3B1.398 (3)
C2A—H2A0.9500C2B—H2B0.9500
C3A—C4A1.376 (3)C3B—C4B1.380 (3)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.394 (3)C4B—C5B1.393 (2)
C4A—H4A0.9500C4B—H4B0.9500
C5A—C6A1.393 (2)C5B—C6B1.389 (2)
C5A—C11A1.453 (2)C5B—C11B1.451 (2)
C6A—O1A1.385 (2)C6B—O1B1.3890 (19)
C7A—C8A1.395 (2)C7B—C12B1.387 (2)
C7A—C12A1.395 (2)C7B—C8B1.398 (2)
C7A—P2A1.8355 (19)C7B—P2B1.8296 (18)
C8A—C9A1.397 (3)C8B—C9B1.395 (2)
C8A—H8A0.9500C8B—H8B0.9500
C9A—C10A1.378 (3)C9B—C10B1.376 (3)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.396 (2)C10B—C11B1.397 (2)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.389 (2)C11B—C12B1.393 (2)
C12A—O1A1.3933 (19)C12B—O1B1.3891 (19)
C21A—C26A1.391 (2)C21B—C22B1.389 (3)
C21A—C22A1.392 (3)C21B—C26B1.390 (2)
C21A—P1A1.8320 (17)C21B—P1B1.8264 (19)
C22A—C23A1.389 (2)C22B—C23B1.383 (3)
C22A—H22A0.9500C22B—H22B0.9500
C23A—C24A1.371 (3)C23B—C24B1.379 (3)
C23A—H23A0.9500C23B—H23B0.9500
C24A—C25A1.382 (3)C24B—C25B1.373 (3)
C24A—H24A0.9500C24B—H24B0.9500
C25A—C26A1.385 (3)C25B—C26B1.380 (3)
C25A—H25A0.9500C25B—H25B0.9500
C26A—H26A0.9500C26B—H26B0.9500
C31A—C32A1.393 (2)C31B—C36B1.389 (3)
C31A—C36A1.398 (2)C31B—C32B1.393 (2)
C31A—P1A1.8344 (18)C31B—P1B1.8331 (18)
C32A—C33A1.383 (2)C32B—C33B1.380 (3)
C32A—H32A0.9500C32B—H32B0.9500
C33A—C34A1.375 (3)C33B—C34B1.377 (3)
C33A—H33A0.9500C33B—H33B0.9500
C34A—C35A1.387 (3)C34B—C35B1.380 (3)
C34A—H34A0.9500C34B—H34B0.9500
C35A—C36A1.379 (3)C35B—C36B1.383 (3)
C35A—H35A0.9500C35B—H35B0.9500
C36A—H36A0.9500C36B—H36B0.9500
C41A—C42A1.391 (2)C41B—C46B1.391 (2)
C41A—C46A1.395 (3)C41B—C42B1.393 (2)
C41A—P2A1.8305 (19)C41B—P2B1.8308 (17)
C42A—C43A1.381 (3)C42B—C43B1.388 (2)
C42A—H42A0.9500C42B—H42B0.9500
C43A—C44A1.373 (3)C43B—C44B1.377 (3)
C43A—H43A0.9500C43B—H43B0.9500
C44A—C45A1.381 (3)C44B—C45B1.383 (3)
C44A—H44A0.9500C44B—H44B0.9500
C45A—C46A1.382 (3)C45B—C46B1.385 (2)
C45A—H45A0.9500C45B—H45B0.9500
C46A—H46A0.9500C46B—H46B0.9500
C51A—C56A1.387 (2)C51B—C56B1.388 (2)
C51A—C52A1.386 (2)C51B—C52B1.388 (3)
C51A—P2A1.8321 (17)C51B—P2B1.8333 (17)
C52A—C53A1.385 (2)C52B—C53B1.392 (2)
C52A—H52A0.9500C52B—H52B0.9500
C53A—C54A1.373 (3)C53B—C54B1.370 (3)
C53A—H53A0.9500C53B—H53B0.9500
C54A—C55A1.375 (3)C54B—C55B1.378 (3)
C54A—H54A0.9500C54B—H54B0.9500
C55A—C56A1.390 (3)C55B—C56B1.384 (2)
C55A—H55A0.9500C55B—H55B0.9500
C56A—H56A0.9500C56B—H56B0.9500
C6A—C1A—C2A114.83 (16)C6B—C1B—C2B114.00 (17)
C6A—C1A—P1A119.91 (14)C6B—C1B—P1B119.76 (14)
C2A—C1A—P1A125.14 (14)C2B—C1B—P1B126.11 (14)
C1A—C2A—C3A121.96 (18)C3B—C2B—C1B122.40 (17)
C1A—C2A—H2A119.0C3B—C2B—H2B118.8
C3A—C2A—H2A119.0C1B—C2B—H2B118.8
C4A—C3A—C2A121.47 (18)C4B—C3B—C2B121.25 (17)
C4A—C3A—H3A119.3C4B—C3B—H3B119.4
C2A—C3A—H3A119.3C2B—C3B—H3B119.4
C3A—C4A—C5A118.23 (17)C3B—C4B—C5B118.25 (18)
C3A—C4A—H4A120.9C3B—C4B—H4B120.9
C5A—C4A—H4A120.9C5B—C4B—H4B120.9
C6A—C5A—C4A119.06 (17)C6B—C5B—C4B118.87 (17)
C6A—C5A—C11A105.72 (16)C6B—C5B—C11B106.04 (15)
C4A—C5A—C11A135.21 (17)C4B—C5B—C11B135.08 (17)
O1A—C6A—C1A123.88 (16)C5B—C6B—O1B111.51 (15)
O1A—C6A—C5A111.64 (15)C5B—C6B—C1B125.21 (17)
C1A—C6A—C5A124.45 (17)O1B—C6B—C1B123.25 (16)
C8A—C7A—C12A113.82 (17)C12B—C7B—C8B114.56 (16)
C8A—C7A—P2A125.20 (15)C12B—C7B—P2B119.20 (13)
C12A—C7A—P2A120.86 (13)C8B—C7B—P2B125.98 (14)
C7A—C8A—C9A122.72 (18)C9B—C8B—C7B122.00 (17)
C7A—C8A—H8A118.6C9B—C8B—H8B119.0
C9A—C8A—H8A118.6C7B—C8B—H8B119.0
C10A—C9A—C8A121.52 (17)C10B—C9B—C8B121.65 (17)
C10A—C9A—H9A119.2C10B—C9B—H9B119.2
C8A—C9A—H9A119.2C8B—C9B—H9B119.2
C9A—C10A—C11A117.71 (18)C9B—C10B—C11B118.18 (17)
C9A—C10A—H10A121.1C9B—C10B—H10B120.9
C11A—C10A—H10A121.1C11B—C10B—H10B120.9
C12A—C11A—C10A119.24 (17)C12B—C11B—C10B118.67 (17)
C12A—C11A—C5A105.80 (15)C12B—C11B—C5B105.53 (15)
C10A—C11A—C5A134.94 (18)C10B—C11B—C5B135.79 (17)
C11A—C12A—O1A111.54 (15)C7B—C12B—O1B123.42 (15)
C11A—C12A—C7A124.97 (16)C7B—C12B—C11B124.93 (16)
O1A—C12A—C7A123.46 (16)O1B—C12B—C11B111.65 (15)
C26A—C21A—C22A117.97 (17)C22B—C21B—C26B117.60 (18)
C26A—C21A—P1A116.93 (15)C22B—C21B—P1B125.56 (14)
C22A—C21A—P1A124.91 (14)C26B—C21B—P1B116.79 (15)
C23A—C22A—C21A120.67 (18)C23B—C22B—C21B121.45 (18)
C23A—C22A—H22A119.7C23B—C22B—H22B119.3
C21A—C22A—H22A119.7C21B—C22B—H22B119.3
C24A—C23A—C22A120.3 (2)C24B—C23B—C22B119.9 (2)
C24A—C23A—H23A119.9C24B—C23B—H23B120.1
C22A—C23A—H23A119.9C22B—C23B—H23B120.1
C23A—C24A—C25A120.18 (18)C25B—C24B—C23B119.5 (2)
C23A—C24A—H24A119.9C25B—C24B—H24B120.2
C25A—C24A—H24A119.9C23B—C24B—H24B120.2
C24A—C25A—C26A119.49 (19)C24B—C25B—C26B120.6 (2)
C24A—C25A—H25A120.3C24B—C25B—H25B119.7
C26A—C25A—H25A120.3C26B—C25B—H25B119.7
C25A—C26A—C21A121.4 (2)C25B—C26B—C21B121.0 (2)
C25A—C26A—H26A119.3C25B—C26B—H26B119.5
C21A—C26A—H26A119.3C21B—C26B—H26B119.5
C32A—C31A—C36A117.80 (16)C36B—C31B—C32B118.20 (18)
C32A—C31A—P1A124.71 (13)C36B—C31B—P1B117.16 (14)
C36A—C31A—P1A117.15 (13)C32B—C31B—P1B124.64 (15)
C33A—C32A—C31A120.80 (16)C33B—C32B—C31B120.61 (19)
C33A—C32A—H32A119.6C33B—C32B—H32B119.7
C31A—C32A—H32A119.6C31B—C32B—H32B119.7
C34A—C33A—C32A120.72 (17)C34B—C33B—C32B120.53 (19)
C34A—C33A—H33A119.6C34B—C33B—H33B119.7
C32A—C33A—H33A119.6C32B—C33B—H33B119.7
C33A—C34A—C35A119.33 (18)C33B—C34B—C35B119.61 (19)
C33A—C34A—H34A120.3C33B—C34B—H34B120.2
C35A—C34A—H34A120.3C35B—C34B—H34B120.2
C36A—C35A—C34A120.18 (17)C34B—C35B—C36B120.05 (19)
C36A—C35A—H35A119.9C34B—C35B—H35B120.0
C34A—C35A—H35A119.9C36B—C35B—H35B120.0
C35A—C36A—C31A121.15 (17)C35B—C36B—C31B120.99 (18)
C35A—C36A—H36A119.4C35B—C36B—H36B119.5
C31A—C36A—H36A119.4C31B—C36B—H36B119.5
C42A—C41A—C46A117.76 (18)C46B—C41B—C42B118.34 (16)
C42A—C41A—P2A117.35 (14)C46B—C41B—P2B125.19 (13)
C46A—C41A—P2A124.89 (14)C42B—C41B—P2B116.47 (13)
C43A—C42A—C41A121.18 (19)C43B—C42B—C41B120.97 (17)
C43A—C42A—H42A119.4C43B—C42B—H42B119.5
C41A—C42A—H42A119.4C41B—C42B—H42B119.5
C44A—C43A—C42A120.2 (2)C44B—C43B—C42B119.72 (17)
C44A—C43A—H43A119.9C44B—C43B—H43B120.1
C42A—C43A—H43A119.9C42B—C43B—H43B120.1
C43A—C44A—C45A119.7 (2)C43B—C44B—C45B120.16 (17)
C43A—C44A—H44A120.2C43B—C44B—H44B119.9
C45A—C44A—H44A120.2C45B—C44B—H44B119.9
C44A—C45A—C46A120.2 (2)C44B—C45B—C46B120.07 (18)
C44A—C45A—H45A119.9C44B—C45B—H45B120.0
C46A—C45A—H45A119.9C46B—C45B—H45B120.0
C45A—C46A—C41A120.89 (19)C45B—C46B—C41B120.73 (17)
C45A—C46A—H46A119.6C45B—C46B—H46B119.6
C41A—C46A—H46A119.6C41B—C46B—H46B119.6
C56A—C51A—C52A118.26 (16)C56B—C51B—C52B118.53 (17)
C56A—C51A—P2A117.54 (14)C56B—C51B—P2B117.23 (15)
C52A—C51A—P2A124.19 (13)C52B—C51B—P2B123.69 (14)
C53A—C52A—C51A121.12 (17)C51B—C52B—C53B120.2 (2)
C53A—C52A—H52A119.4C51B—C52B—H52B119.9
C51A—C52A—H52A119.4C53B—C52B—H52B119.9
C54A—C53A—C52A119.89 (19)C54B—C53B—C52B120.5 (2)
C54A—C53A—H53A120.1C54B—C53B—H53B119.7
C52A—C53A—H53A120.1C52B—C53B—H53B119.7
C53A—C54A—C55A119.98 (17)C53B—C54B—C55B119.83 (18)
C53A—C54A—H54A120.0C53B—C54B—H54B120.1
C55A—C54A—H54A120.0C55B—C54B—H54B120.1
C54A—C55A—C56A120.15 (18)C54B—C55B—C56B119.9 (2)
C54A—C55A—H55A119.9C54B—C55B—H55B120.0
C56A—C55A—H55A119.9C56B—C55B—H55B120.0
C51A—C56A—C55A120.58 (19)C55B—C56B—C51B121.0 (2)
C51A—C56A—H56A119.7C55B—C56B—H56B119.5
C55A—C56A—H56A119.7C51B—C56B—H56B119.5
C6A—O1A—C12A105.30 (13)C12B—O1B—C6B105.27 (13)
C1A—P1A—C21A103.15 (8)C21B—P1B—C1B102.18 (8)
C1A—P1A—C31A102.08 (8)C21B—P1B—C31B101.54 (8)
C21A—P1A—C31A103.78 (8)C1B—P1B—C31B100.47 (8)
C41A—P2A—C51A102.14 (8)C7B—P2B—C41B101.18 (8)
C41A—P2A—C7A100.61 (8)C7B—P2B—C51B103.45 (8)
C51A—P2A—C7A101.40 (8)C41B—P2B—C51B103.28 (8)
C6A—C1A—C2A—C3A0.4 (3)C6B—C1B—C2B—C3B0.2 (3)
P1A—C1A—C2A—C3A176.48 (14)P1B—C1B—C2B—C3B176.01 (14)
C1A—C2A—C3A—C4A0.1 (3)C1B—C2B—C3B—C4B0.9 (3)
C2A—C3A—C4A—C5A0.2 (3)C2B—C3B—C4B—C5B0.7 (3)
C3A—C4A—C5A—C6A0.1 (3)C3B—C4B—C5B—C6B0.4 (3)
C3A—C4A—C5A—C11A178.70 (19)C3B—C4B—C5B—C11B178.09 (19)
C2A—C1A—C6A—O1A178.80 (15)C4B—C5B—C6B—O1B179.74 (15)
P1A—C1A—C6A—O1A4.9 (2)C11B—C5B—C6B—O1B0.82 (19)
C2A—C1A—C6A—C5A0.5 (3)C4B—C5B—C6B—C1B1.6 (3)
P1A—C1A—C6A—C5A176.79 (13)C11B—C5B—C6B—C1B177.31 (16)
C4A—C5A—C6A—O1A178.72 (15)C2B—C1B—C6B—C5B1.4 (3)
C11A—C5A—C6A—O1A0.23 (19)P1B—C1B—C6B—C5B177.55 (13)
C4A—C5A—C6A—C1A0.2 (3)C2B—C1B—C6B—O1B179.36 (15)
C11A—C5A—C6A—C1A178.70 (16)P1B—C1B—C6B—O1B4.5 (2)
C12A—C7A—C8A—C9A0.4 (3)C12B—C7B—C8B—C9B0.3 (2)
P2A—C7A—C8A—C9A175.70 (14)P2B—C7B—C8B—C9B174.34 (14)
C7A—C8A—C9A—C10A1.4 (3)C7B—C8B—C9B—C10B0.4 (3)
C8A—C9A—C10A—C11A1.1 (3)C8B—C9B—C10B—C11B0.1 (3)
C9A—C10A—C11A—C12A0.1 (3)C9B—C10B—C11B—C12B0.3 (3)
C9A—C10A—C11A—C5A177.58 (19)C9B—C10B—C11B—C5B179.99 (19)
C6A—C5A—C11A—C12A0.64 (18)C6B—C5B—C11B—C12B0.66 (19)
C4A—C5A—C11A—C12A178.05 (19)C4B—C5B—C11B—C12B179.32 (19)
C6A—C5A—C11A—C10A178.57 (19)C6B—C5B—C11B—C10B179.04 (19)
C4A—C5A—C11A—C10A0.1 (4)C4B—C5B—C11B—C10B0.4 (4)
C10A—C11A—C12A—O1A179.17 (15)C8B—C7B—C12B—O1B179.80 (15)
C5A—C11A—C12A—O1A0.86 (19)P2B—C7B—C12B—O1B5.8 (2)
C10A—C11A—C12A—C7A1.3 (3)C8B—C7B—C12B—C11B0.1 (3)
C5A—C11A—C12A—C7A177.07 (16)P2B—C7B—C12B—C11B174.35 (14)
C8A—C7A—C12A—C11A1.0 (3)C10B—C11B—C12B—C7B0.4 (3)
P2A—C7A—C12A—C11A177.23 (13)C5B—C11B—C12B—C7B179.80 (16)
C8A—C7A—C12A—O1A178.66 (15)C10B—C11B—C12B—O1B179.47 (15)
P2A—C7A—C12A—O1A5.1 (2)C5B—C11B—C12B—O1B0.30 (19)
C26A—C21A—C22A—C23A0.9 (3)C26B—C21B—C22B—C23B1.1 (3)
P1A—C21A—C22A—C23A173.89 (15)P1B—C21B—C22B—C23B176.26 (15)
C21A—C22A—C23A—C24A1.2 (3)C21B—C22B—C23B—C24B0.7 (3)
C22A—C23A—C24A—C25A0.3 (3)C22B—C23B—C24B—C25B0.2 (3)
C23A—C24A—C25A—C26A0.8 (3)C23B—C24B—C25B—C26B0.1 (3)
C24A—C25A—C26A—C21A1.1 (3)C24B—C25B—C26B—C21B0.5 (3)
C22A—C21A—C26A—C25A0.3 (3)C22B—C21B—C26B—C25B1.0 (3)
P1A—C21A—C26A—C25A175.45 (15)P1B—C21B—C26B—C25B176.59 (15)
C36A—C31A—C32A—C33A1.1 (3)C36B—C31B—C32B—C33B0.9 (3)
P1A—C31A—C32A—C33A171.98 (15)P1B—C31B—C32B—C33B178.46 (16)
C31A—C32A—C33A—C34A1.1 (3)C31B—C32B—C33B—C34B0.4 (3)
C32A—C33A—C34A—C35A0.2 (3)C32B—C33B—C34B—C35B1.0 (3)
C33A—C34A—C35A—C36A1.3 (3)C33B—C34B—C35B—C36B0.2 (3)
C34A—C35A—C36A—C31A1.3 (3)C34B—C35B—C36B—C31B1.1 (3)
C32A—C31A—C36A—C35A0.0 (3)C32B—C31B—C36B—C35B1.6 (3)
P1A—C31A—C36A—C35A173.67 (16)P1B—C31B—C36B—C35B177.78 (14)
C46A—C41A—C42A—C43A1.0 (3)C46B—C41B—C42B—C43B1.7 (3)
P2A—C41A—C42A—C43A178.54 (15)P2B—C41B—C42B—C43B178.82 (14)
C41A—C42A—C43A—C44A0.8 (3)C41B—C42B—C43B—C44B1.0 (3)
C42A—C43A—C44A—C45A0.0 (3)C42B—C43B—C44B—C45B0.3 (3)
C43A—C44A—C45A—C46A0.4 (3)C43B—C44B—C45B—C46B0.9 (3)
C44A—C45A—C46A—C41A0.0 (3)C44B—C45B—C46B—C41B0.1 (3)
C42A—C41A—C46A—C45A0.6 (3)C42B—C41B—C46B—C45B1.2 (3)
P2A—C41A—C46A—C45A178.90 (16)P2B—C41B—C46B—C45B179.43 (14)
C56A—C51A—C52A—C53A0.1 (3)C56B—C51B—C52B—C53B0.8 (3)
P2A—C51A—C52A—C53A178.74 (14)P2B—C51B—C52B—C53B170.45 (15)
C51A—C52A—C53A—C54A0.3 (3)C51B—C52B—C53B—C54B0.5 (3)
C52A—C53A—C54A—C55A0.0 (3)C52B—C53B—C54B—C55B0.5 (3)
C53A—C54A—C55A—C56A0.7 (3)C53B—C54B—C55B—C56B1.2 (3)
C52A—C51A—C56A—C55A0.7 (3)C54B—C55B—C56B—C51B0.9 (3)
P2A—C51A—C56A—C55A178.18 (16)C52B—C51B—C56B—C55B0.1 (3)
C54A—C55A—C56A—C51A1.0 (3)P2B—C51B—C56B—C55B171.70 (14)
C1A—C6A—O1A—C12A178.20 (16)C7B—C12B—O1B—C6B179.72 (15)
C5A—C6A—O1A—C12A0.28 (18)C11B—C12B—O1B—C6B0.19 (18)
C11A—C12A—O1A—C6A0.72 (18)C5B—C6B—O1B—C12B0.64 (18)
C7A—C12A—O1A—C6A177.24 (16)C1B—C6B—O1B—C12B177.53 (16)
C6A—C1A—P1A—C21A85.02 (15)C22B—C21B—P1B—C1B16.60 (18)
C2A—C1A—P1A—C21A99.11 (16)C26B—C21B—P1B—C1B166.02 (14)
C6A—C1A—P1A—C31A167.50 (14)C22B—C21B—P1B—C31B86.92 (17)
C2A—C1A—P1A—C31A8.36 (17)C26B—C21B—P1B—C31B90.45 (15)
C26A—C21A—P1A—C1A175.24 (14)C6B—C1B—P1B—C21B75.77 (15)
C22A—C21A—P1A—C1A0.44 (18)C2B—C1B—P1B—C21B108.63 (16)
C26A—C21A—P1A—C31A78.58 (16)C6B—C1B—P1B—C31B179.86 (14)
C22A—C21A—P1A—C31A106.62 (17)C2B—C1B—P1B—C31B4.27 (18)
C32A—C31A—P1A—C1A112.56 (16)C36B—C31B—P1B—C21B160.73 (15)
C36A—C31A—P1A—C1A74.27 (16)C32B—C31B—P1B—C21B19.90 (19)
C32A—C31A—P1A—C21A5.57 (18)C36B—C31B—P1B—C1B94.39 (15)
C36A—C31A—P1A—C21A178.75 (14)C32B—C31B—P1B—C1B84.98 (18)
C42A—C41A—P2A—C51A158.45 (14)C12B—C7B—P2B—C41B169.08 (13)
C46A—C41A—P2A—C51A22.01 (19)C8B—C7B—P2B—C41B4.67 (17)
C42A—C41A—P2A—C7A97.31 (15)C12B—C7B—P2B—C51B84.18 (14)
C46A—C41A—P2A—C7A82.23 (18)C8B—C7B—P2B—C51B102.07 (16)
C56A—C51A—P2A—C41A92.30 (16)C46B—C41B—P2B—C7B81.32 (16)
C52A—C51A—P2A—C41A86.51 (17)C42B—C41B—P2B—C7B99.27 (14)
C56A—C51A—P2A—C7A164.08 (15)C46B—C41B—P2B—C51B25.55 (17)
C52A—C51A—P2A—C7A17.11 (18)C42B—C41B—P2B—C51B153.86 (13)
C8A—C7A—P2A—C41A8.64 (17)C56B—C51B—P2B—C7B166.96 (14)
C12A—C7A—P2A—C41A175.55 (14)C52B—C51B—P2B—C7B21.73 (18)
C8A—C7A—P2A—C51A113.48 (16)C56B—C51B—P2B—C41B61.82 (16)
C12A—C7A—P2A—C51A70.72 (15)C52B—C51B—P2B—C41B126.87 (16)

Experimental details

Crystal data
Chemical formulaC36H26OP2
Mr536.51
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)11.7463 (2), 14.7238 (3), 16.7140 (4)
α, β, γ (°)96.821 (2), 96.351 (5), 95.240 (2)
V3)2836.58 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.40 × 0.22 × 0.18
Data collection
DiffractometerBruker APEXII CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
28406, 12364, 8323
Rint0.052
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.100, 0.90
No. of reflections12363
No. of parameters703
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.30

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We thank Dr Manuel Fernandes for the data collection and SASOL, THRIP and the University of KwaZulu-Natal for financial support.

References

First citationBanerjee, A. (1973). Acta Cryst. B29, 2070–2074.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationBruker (2005). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDideberg, O., Dupont, L. & André, J. M. (1972). Acta Cryst. B28, 1002–1007.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationHillebrand, S., Bruckmann, J., Kruger, C. & Haenel, M. W. (1995). Tetrahedron Lett. 36, 75–78.  CSD CrossRef CAS Web of Science Google Scholar
First citationKranenburg, M., Vanderburgt, Y. E. M., Kamer, P. C. J., van Leeuwen, P. W. N. M., Goubitz, K. & Fraanje, J. (1995). Organometallics, 14, 3081–3089.  CrossRef CAS Web of Science Google Scholar
First citationMarimuthu, T., Bala, M. D. & Friedrich, H. B. (2008a). Acta Cryst. E64, o711.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMarimuthu, T., Bala, M. D. & Friedrich, H. B. (2008b). Acta Cryst. E64, o772.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationReppart, W. J., Gallucci, J. C., Lundstedt, A. P. & Gerkin, R. E. (1984). Acta Cryst. C40, 1572–1576.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationVogl, E. M., Bruckmann, J., Krüger, C. & Haenel, M. W. (1996). J. Organomet. Chem. 520, 249–252.  CSD CrossRef CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds