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

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ISSN: 2414-3146

6,6′-[(3,3′-Di-tert-butyl-5,5′-dimeth­­oxy-1,1′-bi­phenyl-2,2′-di­yl)bis­(­oxy)]bis­­(dibenzo[d,f][1,3,2]dioxaphosphepine) benzene monosolvate

aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany, bEvonik Performance Materials GmbH, Paul-Baumann-Str. 1, 45772 Marl, Germany, and cLehrstuhl für Theoretische Chemie, Ruhr-Universität Bochum, 44780 Bochum, Germany
*Correspondence e-mail: christoph.kubis@catalysis.de, robert.franke@evonik.com

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 21 November 2019; accepted 4 December 2019; online 10 December 2019)

The crystal structure of the benzene monosolvate of the well known organic diphosphite ligand BIPHEPHOS, C46H44O8P2·C6H6, is reported for the first time. Single crystals of BIPHEPHOS were obtained from a benzene solution after layering with n-heptane at room temperature. One specific property of this type of diphosphite structure is the twisting of the biphenyl units. In the crystal, C—H⋯π contacts and ππ stacking inter­actions [centroid-to-centroid distance = 3.8941 (15) Å] are observed.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

BIPHEPHOS is a very prominent organic diphosphite ligand applied as co-catalyst in the field of highly n-regioselective rhodium-catalysed alkene hydro­formyl­ation (Börner & Franke, 2016[Börner, A. & Franke, R. (2016). Hydroformylation. Weinheim: Wiley-VCH.]). Atropisomerism of the dibenzo[d,f][1,3,2]dioxaphosphepine moiety in related diphosphites has been studied in solution and by DFT methods (Whiteker et al., 1995[Whiteker, G. T., Harrison, A. M. & Abatjoglou, A. G. (1995). J. Chem. Soc. Chem. Commun. pp. 1805-1806.], Briggs & Whiteker, 2001[Briggs, J. R. & Whiteker, G. T. (2001). Chem. Commun. pp. 2174-2175.], Franke et al., 2003[Franke, R., Borgmann, C., Hess, D. & Wiese, K.-D. (2003). Z. Anorg. Allg. Chem. 629, 2535-2538.]). Inter­estingly, until now no crystal structure of BIPHEPHOS has been reported. Crystal structures have been published for similar diphosphites containing the same dibenzo[d,f][1,3,2]dioxaphosphepine unit but with the unsubstituted 2,2′-di­hydroxy­biphenyl and the 2,2′-dihy­droxy-3,3′,5,5′-tetra­(t-but­yl)biphenyl backbone (Baker et al., 1991[Baker, M. J., Harrison, K. N., Orpen, A. G., Pringle, P. G. & Shaw, G. (1991). J. Chem. Soc. Chem. Commun. pp. 803-804.]; Meyer et al., 1993[Meyer, T. G., Fischer, A., Jones, P. G. & Schmutzler, R. (1993). Z. Naturforsch. B, 48, 659-671.]; Hao et al., 2012[Hao, Y., Guo, H.-R., Zhu, L.-Q. & Feng, J. (2012). Chin. J. Struct. Chem. 31, 673-676.]; Liu et al., 2014[Liu, Y.-H., Howell, D. K., Stanley, G. G. & Fronczek, F. R. (2014). Private Communication (refcode CCDC 994753). CCDC, Cambridge, England. DOI: 10.5517/cc12d3td.]). The common feature of these types of ligands is the twisting about the biphenyl linkages. For the title compound (Fig. 1[link]), the dihedral angle about the biphenyl axis of the backbone between the C1–C6 and C7–C12 planes is 61.79 (10)°. Within the seven-membered rings, the dihedral angles about the biphenyl units are 43.83 (11)° for C2–C28/C29–C34 and 41.78 (11)° for C35–C40/C41–C46.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are omitted for clarity.

Crystals of the title compound contain co-crystallized solvent (one benzene per one mol­ecule diphosphite), which inter­acts with the ligand via C—H⋯π inter­actions (Table 1[link]). In the crystal, centrosymmetrically related mol­ecules are linked by a ππ stacking inter­action involving the C23–C28 rings with a centroid-to-centroid distance of 3.8941 (15) Å.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C47–C52 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C39—H39⋯Cg1i 0.95 2.75 3.678 (3) 165
Symmetry code: (i) x, y-1, z.

Synthesis and crystallization

The diphosphite was provided by Evonik Performance Materials GmbH (OxoPhos® 17). A solution of C46H44O8P2 (0.08 mmol, 0.063 g) in benzene (2 ml) was prepared under argon using standard Schlenk techniques. The solution was brought to 50°C for dissolving the solid material. At room temperature the solution was then layered with ca 0.4 ml of n-heptane. Crystallization as fine needles took place at room temperature after several days.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C46H44O8P2·C6H6
Mr 864.86
Crystal system, space group Monoclinic, P21/c
Temperature (K) 150
a, b, c (Å) 25.1072 (5), 8.8634 (2), 21.3401 (4)
β (°) 112.4441 (12)
V3) 4389.20 (16)
Z 4
Radiation type Cu Kα
μ (mm−1) 1.36
Crystal size (mm) 0.34 × 0.04 × 0.04
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2014[Bruker (2014). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.80, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections 41898, 7745, 5805
Rint 0.067
(sin θ/λ)max−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.107, 1.01
No. of reflections 7745
No. of parameters 567
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.25, −0.34
Computer programs: APEX2 (Bruker, 2014[Bruker (2014). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2013[Bruker (2013). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), XP in SHELXTL and SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014/7 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

6,6'-[(3,3'-Di-tert-butyl-5,5'-dimethoxy-1,1'-biphenyl-2,2'-diyl)bis(oxy)]bis(dibenzo[d,f][1,3,2]dioxaphosphepine) benzene monosolvate top
Crystal data top
C46H44O8P2·C6H6F(000) = 1824
Mr = 864.86Dx = 1.309 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 25.1072 (5) ÅCell parameters from 4431 reflections
b = 8.8634 (2) Åθ = 3.8–66.5°
c = 21.3401 (4) ŵ = 1.36 mm1
β = 112.4441 (12)°T = 150 K
V = 4389.20 (16) Å3Needle, colourless
Z = 40.34 × 0.04 × 0.04 mm
Data collection top
Bruker APEXII CCD
diffractometer
7745 independent reflections
Radiation source: microfocus5805 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.067
Detector resolution: 8.3333 pixels mm-1θmax = 66.7°, θmin = 1.9°
φ and ω scansh = 2929
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
k = 109
Tmin = 0.80, Tmax = 0.95l = 2525
41898 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0532P)2 + 0.4402P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
7745 reflectionsΔρmax = 0.25 e Å3
567 parametersΔρmin = 0.34 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms were placed geometrically and refined using a riding atom approximation, with C–H = 0.95–0.98 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. A rotating model was used for the methyl groups.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.21470 (8)0.4417 (2)0.51667 (10)0.0260 (4)
C20.15970 (9)0.3898 (3)0.47514 (10)0.0296 (4)
C30.11333 (9)0.4728 (3)0.47748 (10)0.0318 (4)
H30.07540.44170.44990.038*
C40.12035 (9)0.5992 (3)0.51846 (10)0.0318 (4)
C50.17481 (9)0.6423 (2)0.56151 (10)0.0290 (4)
H50.17980.72610.59090.035*
C60.22288 (8)0.5612 (2)0.56154 (9)0.0260 (4)
C70.28090 (8)0.6109 (2)0.61018 (9)0.0257 (4)
C80.29895 (9)0.7562 (2)0.60285 (9)0.0275 (4)
H80.27520.81920.56710.033*
C90.35139 (9)0.8083 (2)0.64762 (10)0.0271 (4)
C100.38784 (8)0.7113 (2)0.69685 (10)0.0274 (4)
H100.42530.74570.72460.033*
C110.37152 (8)0.5665 (2)0.70686 (9)0.0255 (4)
C120.31566 (8)0.5203 (2)0.66410 (9)0.0248 (4)
C130.14907 (9)0.2501 (3)0.42951 (11)0.0357 (5)
C140.18159 (10)0.1141 (3)0.47133 (12)0.0382 (5)
H14A0.22310.13400.48900.057*
H14B0.17310.02410.44250.057*
H14C0.16930.09740.50920.057*
C150.16772 (11)0.2851 (3)0.37019 (11)0.0430 (6)
H15A0.14520.37020.34400.065*
H15B0.16110.19620.34080.065*
H15C0.20880.31100.38800.065*
C160.08521 (11)0.2061 (3)0.39926 (15)0.0552 (7)
H16A0.07130.19080.43590.083*
H16B0.08060.11250.37320.083*
H16C0.06300.28680.36930.083*
C170.07469 (11)0.7922 (3)0.55768 (15)0.0536 (7)
H17A0.09150.75730.60480.080*
H17B0.03640.83440.54840.080*
H17C0.09950.87000.55040.080*
C180.33003 (10)1.0591 (2)0.60870 (11)0.0333 (5)
H18A0.31481.02910.56090.050*
H18B0.34831.15850.61350.050*
H18C0.29851.06390.62500.050*
C190.41356 (8)0.4679 (2)0.76405 (10)0.0278 (4)
C200.39320 (9)0.4608 (3)0.82366 (10)0.0317 (4)
H20A0.35450.41680.80800.048*
H20B0.39230.56290.84090.048*
H20C0.41990.39820.85990.048*
C210.47487 (9)0.5340 (3)0.79171 (11)0.0360 (5)
H21A0.50110.46400.82470.054*
H21B0.47480.63100.81380.054*
H21C0.48780.54920.75420.054*
C220.41810 (9)0.3085 (3)0.73876 (10)0.0317 (4)
H22A0.43030.31450.70030.048*
H22B0.38050.25870.72440.048*
H22C0.44650.25030.77540.048*
C230.42077 (9)0.4076 (3)0.56208 (10)0.0300 (4)
C240.45812 (9)0.5236 (3)0.59366 (10)0.0343 (5)
H240.44530.60700.61210.041*
C250.51494 (10)0.5166 (3)0.59814 (11)0.0397 (5)
H250.54110.59580.61940.048*
C260.53311 (9)0.3941 (3)0.57156 (11)0.0408 (6)
H260.57180.38950.57460.049*
C270.49539 (9)0.2779 (3)0.54057 (11)0.0368 (5)
H270.50860.19390.52290.044*
C280.43789 (9)0.2825 (3)0.53483 (10)0.0310 (4)
C290.39772 (9)0.1581 (3)0.50225 (10)0.0309 (4)
C300.41526 (10)0.0076 (3)0.51498 (11)0.0352 (5)
H300.45340.01420.54560.042*
C310.37855 (10)0.1101 (3)0.48411 (11)0.0385 (5)
H310.39120.21140.49460.046*
C320.32335 (10)0.0804 (3)0.43777 (11)0.0375 (5)
H320.29840.16130.41580.045*
C330.30467 (9)0.0682 (3)0.42360 (10)0.0332 (5)
H330.26720.08950.39120.040*
C340.34123 (9)0.1848 (3)0.45714 (10)0.0293 (4)
C350.15006 (9)0.2095 (3)0.64810 (10)0.0298 (4)
C360.09582 (10)0.2675 (3)0.61247 (11)0.0363 (5)
H360.09110.35260.58380.044*
C370.04799 (10)0.2002 (3)0.61888 (12)0.0401 (5)
H370.01050.23920.59470.048*
C380.05564 (9)0.0756 (3)0.66094 (12)0.0375 (5)
H380.02310.02870.66510.045*
C390.11007 (9)0.0195 (3)0.69661 (11)0.0330 (5)
H390.11470.06530.72540.040*
C400.15884 (9)0.0861 (2)0.69093 (10)0.0288 (4)
C410.21719 (9)0.0226 (2)0.72726 (10)0.0279 (4)
C420.22625 (9)0.1325 (3)0.73141 (10)0.0320 (4)
H420.19440.19840.71130.038*
C430.28060 (10)0.1929 (3)0.76411 (11)0.0369 (5)
H430.28590.29920.76640.044*
C440.32739 (10)0.0979 (3)0.79350 (11)0.0372 (5)
H440.36490.13910.81510.045*
C450.31965 (9)0.0563 (3)0.79145 (10)0.0334 (5)
H450.35160.12130.81260.040*
C460.26507 (9)0.1158 (2)0.75833 (9)0.0284 (4)
C470.04143 (12)0.7196 (4)0.77065 (14)0.0537 (7)
H470.00190.74580.75630.064*
C480.05877 (12)0.6181 (4)0.73342 (14)0.0540 (7)
H480.03110.57400.69370.065*
C490.11611 (13)0.5804 (3)0.75358 (15)0.0550 (7)
H490.12810.51030.72800.066*
C500.15594 (13)0.6450 (4)0.81117 (17)0.0627 (9)
H500.19560.62030.82520.075*
C510.13798 (15)0.7463 (4)0.84858 (15)0.0629 (8)
H510.16540.79030.88850.076*
C520.08077 (14)0.7832 (4)0.82824 (14)0.0590 (7)
H520.06850.85240.85400.071*
O10.26355 (6)0.36536 (16)0.51544 (7)0.0273 (3)
O20.36542 (6)0.40936 (17)0.56232 (7)0.0294 (3)
O30.32105 (6)0.33231 (17)0.44072 (7)0.0309 (3)
O40.29329 (6)0.38073 (16)0.67427 (7)0.0265 (3)
O50.19750 (6)0.27103 (17)0.63783 (7)0.0309 (3)
O60.25769 (6)0.27110 (17)0.76141 (7)0.0310 (3)
O70.06992 (7)0.6688 (2)0.51339 (8)0.0427 (4)
O80.37168 (7)0.95099 (17)0.64772 (7)0.0337 (3)
P10.31057 (2)0.45307 (6)0.49248 (2)0.02799 (13)
P20.23811 (2)0.38617 (6)0.69709 (3)0.02787 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0238 (9)0.0298 (11)0.0245 (9)0.0053 (8)0.0094 (8)0.0046 (8)
C20.0302 (10)0.0345 (12)0.0224 (9)0.0016 (8)0.0081 (8)0.0001 (8)
C30.0246 (10)0.0404 (13)0.0268 (10)0.0017 (8)0.0057 (8)0.0021 (8)
C40.0266 (10)0.0397 (13)0.0273 (10)0.0085 (9)0.0083 (8)0.0012 (9)
C50.0301 (10)0.0300 (11)0.0259 (9)0.0030 (8)0.0096 (8)0.0008 (8)
C60.0268 (10)0.0276 (11)0.0231 (9)0.0009 (8)0.0090 (8)0.0032 (7)
C70.0267 (10)0.0297 (11)0.0229 (9)0.0006 (8)0.0119 (8)0.0013 (7)
C80.0307 (10)0.0286 (11)0.0228 (9)0.0024 (8)0.0100 (8)0.0026 (8)
C90.0310 (10)0.0268 (11)0.0258 (9)0.0033 (8)0.0132 (8)0.0003 (8)
C100.0258 (10)0.0332 (12)0.0237 (9)0.0031 (8)0.0100 (8)0.0029 (8)
C110.0263 (10)0.0294 (11)0.0241 (9)0.0004 (8)0.0133 (8)0.0007 (7)
C120.0269 (10)0.0255 (11)0.0248 (9)0.0008 (8)0.0131 (8)0.0010 (7)
C130.0310 (11)0.0398 (13)0.0325 (10)0.0000 (9)0.0079 (9)0.0093 (9)
C140.0420 (12)0.0331 (12)0.0401 (12)0.0030 (9)0.0162 (10)0.0069 (9)
C150.0471 (14)0.0492 (15)0.0258 (10)0.0085 (11)0.0061 (10)0.0075 (9)
C160.0358 (13)0.0578 (18)0.0619 (17)0.0049 (11)0.0075 (12)0.0290 (14)
C170.0395 (14)0.0598 (18)0.0567 (15)0.0138 (12)0.0130 (12)0.0185 (13)
C180.0458 (13)0.0247 (11)0.0308 (10)0.0010 (9)0.0162 (9)0.0020 (8)
C190.0261 (10)0.0337 (12)0.0229 (9)0.0010 (8)0.0086 (8)0.0018 (8)
C200.0336 (11)0.0388 (12)0.0225 (9)0.0013 (9)0.0105 (8)0.0014 (8)
C210.0276 (11)0.0433 (13)0.0328 (10)0.0002 (9)0.0069 (9)0.0054 (9)
C220.0328 (11)0.0356 (12)0.0266 (10)0.0062 (9)0.0112 (8)0.0029 (8)
C230.0276 (10)0.0404 (13)0.0245 (9)0.0022 (8)0.0128 (8)0.0025 (8)
C240.0343 (11)0.0431 (13)0.0269 (10)0.0024 (9)0.0133 (9)0.0038 (9)
C250.0297 (11)0.0571 (16)0.0311 (11)0.0083 (10)0.0104 (9)0.0037 (10)
C260.0265 (11)0.0679 (17)0.0294 (10)0.0005 (10)0.0122 (9)0.0010 (10)
C270.0316 (11)0.0525 (15)0.0287 (10)0.0071 (10)0.0144 (9)0.0026 (9)
C280.0307 (10)0.0397 (13)0.0250 (9)0.0054 (9)0.0134 (8)0.0037 (8)
C290.0340 (11)0.0380 (12)0.0255 (9)0.0045 (9)0.0169 (9)0.0002 (8)
C300.0366 (11)0.0419 (13)0.0299 (10)0.0095 (9)0.0158 (9)0.0003 (9)
C310.0487 (13)0.0351 (13)0.0383 (11)0.0065 (10)0.0238 (11)0.0002 (9)
C320.0425 (13)0.0394 (13)0.0359 (11)0.0028 (10)0.0207 (10)0.0079 (9)
C330.0347 (11)0.0418 (13)0.0253 (9)0.0018 (9)0.0140 (9)0.0031 (8)
C340.0346 (11)0.0345 (12)0.0232 (9)0.0051 (9)0.0161 (8)0.0013 (8)
C350.0290 (10)0.0349 (12)0.0268 (9)0.0040 (8)0.0121 (8)0.0025 (8)
C360.0324 (11)0.0399 (13)0.0340 (11)0.0007 (9)0.0099 (9)0.0035 (9)
C370.0282 (11)0.0482 (15)0.0418 (12)0.0007 (9)0.0111 (10)0.0012 (10)
C380.0291 (11)0.0461 (14)0.0403 (11)0.0059 (9)0.0167 (9)0.0050 (10)
C390.0352 (11)0.0360 (13)0.0323 (10)0.0048 (9)0.0179 (9)0.0027 (9)
C400.0282 (10)0.0344 (12)0.0255 (9)0.0032 (8)0.0121 (8)0.0046 (8)
C410.0311 (10)0.0327 (12)0.0239 (9)0.0021 (8)0.0149 (8)0.0015 (8)
C420.0342 (11)0.0349 (12)0.0287 (10)0.0028 (9)0.0139 (9)0.0030 (8)
C430.0430 (12)0.0338 (13)0.0338 (11)0.0029 (9)0.0147 (10)0.0019 (9)
C440.0332 (11)0.0451 (14)0.0310 (10)0.0078 (10)0.0099 (9)0.0001 (9)
C450.0317 (11)0.0438 (13)0.0238 (9)0.0033 (9)0.0095 (8)0.0029 (8)
C460.0324 (10)0.0332 (11)0.0221 (9)0.0015 (8)0.0131 (8)0.0000 (8)
C470.0491 (15)0.0670 (19)0.0527 (15)0.0009 (13)0.0281 (13)0.0081 (13)
C480.0528 (16)0.0603 (18)0.0471 (14)0.0054 (13)0.0170 (12)0.0015 (12)
C490.0605 (17)0.0547 (18)0.0553 (16)0.0096 (13)0.0284 (14)0.0104 (13)
C500.0435 (15)0.068 (2)0.072 (2)0.0043 (13)0.0163 (14)0.0379 (17)
C510.071 (2)0.061 (2)0.0418 (14)0.0161 (15)0.0046 (14)0.0121 (13)
C520.074 (2)0.0626 (19)0.0441 (14)0.0003 (15)0.0271 (14)0.0040 (13)
O10.0252 (7)0.0294 (8)0.0279 (7)0.0021 (5)0.0109 (6)0.0002 (5)
O20.0253 (7)0.0385 (9)0.0265 (7)0.0002 (6)0.0122 (6)0.0024 (6)
O30.0357 (8)0.0337 (8)0.0245 (7)0.0034 (6)0.0129 (6)0.0021 (6)
O40.0268 (7)0.0266 (7)0.0274 (7)0.0005 (5)0.0120 (6)0.0007 (5)
O50.0300 (7)0.0366 (8)0.0263 (7)0.0065 (6)0.0111 (6)0.0007 (6)
O60.0363 (8)0.0314 (8)0.0262 (7)0.0050 (6)0.0131 (6)0.0023 (6)
O70.0274 (8)0.0520 (11)0.0421 (9)0.0098 (7)0.0058 (7)0.0125 (7)
O80.0359 (8)0.0289 (8)0.0325 (7)0.0056 (6)0.0089 (6)0.0040 (6)
P10.0297 (3)0.0298 (3)0.0263 (2)0.0013 (2)0.0127 (2)0.00127 (19)
P20.0283 (3)0.0292 (3)0.0284 (2)0.0014 (2)0.0133 (2)0.0002 (2)
Geometric parameters (Å, º) top
C1—C61.390 (3)C25—C261.381 (4)
C1—C21.403 (3)C25—H250.9500
C1—O11.409 (2)C26—C271.384 (4)
C2—C31.394 (3)C26—H260.9500
C2—C131.534 (3)C27—C281.402 (3)
C3—C41.390 (3)C27—H270.9500
C3—H30.9500C28—C291.476 (3)
C4—O71.375 (3)C29—C341.397 (3)
C4—C51.379 (3)C29—C301.398 (3)
C5—C61.404 (3)C30—C311.381 (4)
C5—H50.9500C30—H300.9500
C6—C71.496 (3)C31—C321.386 (3)
C7—C81.394 (3)C31—H310.9500
C7—C121.401 (3)C32—C331.393 (3)
C8—C91.378 (3)C32—H320.9500
C8—H80.9500C33—C341.386 (3)
C9—O81.364 (3)C33—H330.9500
C9—C101.395 (3)C34—O31.397 (3)
C10—C111.389 (3)C35—C361.380 (3)
C10—H100.9500C35—C401.388 (3)
C11—C121.411 (3)C35—O51.401 (2)
C11—C191.544 (3)C36—C371.394 (3)
C12—O41.409 (2)C36—H360.9500
C13—C161.533 (3)C37—C381.390 (4)
C13—C141.536 (3)C37—H370.9500
C13—C151.540 (3)C38—C391.379 (3)
C14—H14A0.9800C38—H380.9500
C14—H14B0.9800C39—C401.406 (3)
C14—H14C0.9800C39—H390.9500
C15—H15A0.9800C40—C411.482 (3)
C15—H15B0.9800C41—C421.391 (3)
C15—H15C0.9800C41—C461.399 (3)
C16—H16A0.9800C42—C431.381 (3)
C16—H16B0.9800C42—H420.9500
C16—H16C0.9800C43—C441.386 (3)
C17—O71.420 (3)C43—H430.9500
C17—H17A0.9800C44—C451.379 (3)
C17—H17B0.9800C44—H440.9500
C17—H17C0.9800C45—C461.384 (3)
C18—O81.428 (3)C45—H450.9500
C18—H18A0.9800C46—O61.394 (3)
C18—H18B0.9800C47—C521.370 (4)
C18—H18C0.9800C47—C481.376 (4)
C19—C221.532 (3)C47—H470.9500
C19—C211.539 (3)C48—C491.377 (4)
C19—C201.543 (3)C48—H480.9500
C20—H20A0.9800C49—C501.379 (5)
C20—H20B0.9800C49—H490.9500
C20—H20C0.9800C50—C511.386 (5)
C21—H21A0.9800C50—H500.9500
C21—H21B0.9800C51—C521.372 (5)
C21—H21C0.9800C51—H510.9500
C22—H22A0.9800C52—H520.9500
C22—H22B0.9800O1—P11.6372 (14)
C22—H22C0.9800O2—P11.6433 (14)
C23—C241.381 (3)O3—P11.6300 (15)
C23—O21.392 (2)O4—P21.6352 (13)
C23—C281.394 (3)O5—P21.6419 (15)
C24—C251.394 (3)O6—P21.6282 (15)
C24—H240.9500
C6—C1—C2122.39 (18)C23—C24—H24120.4
C6—C1—O1118.55 (17)C25—C24—H24120.4
C2—C1—O1118.98 (18)C26—C25—C24119.8 (2)
C3—C2—C1116.0 (2)C26—C25—H25120.1
C3—C2—C13120.23 (19)C24—C25—H25120.1
C1—C2—C13123.77 (19)C25—C26—C27120.5 (2)
C4—C3—C2122.7 (2)C25—C26—H26119.7
C4—C3—H3118.6C27—C26—H26119.7
C2—C3—H3118.6C26—C27—C28121.0 (2)
O7—C4—C5125.3 (2)C26—C27—H27119.5
O7—C4—C3114.84 (19)C28—C27—H27119.5
C5—C4—C3119.86 (19)C23—C28—C27117.2 (2)
C4—C5—C6119.48 (19)C23—C28—C29121.77 (19)
C4—C5—H5120.3C27—C28—C29121.0 (2)
C6—C5—H5120.3C34—C29—C30117.2 (2)
C1—C6—C5119.26 (18)C34—C29—C28121.9 (2)
C1—C6—C7123.42 (18)C30—C29—C28120.9 (2)
C5—C6—C7117.31 (18)C31—C30—C29121.6 (2)
C8—C7—C12119.64 (18)C31—C30—H30119.2
C8—C7—C6117.78 (17)C29—C30—H30119.2
C12—C7—C6122.49 (18)C30—C31—C32120.0 (2)
C9—C8—C7119.79 (18)C30—C31—H31120.0
C9—C8—H8120.1C32—C31—H31120.0
C7—C8—H8120.1C31—C32—C33119.8 (2)
O8—C9—C8124.69 (19)C31—C32—H32120.1
O8—C9—C10115.65 (18)C33—C32—H32120.1
C8—C9—C10119.66 (19)C34—C33—C32119.4 (2)
C11—C10—C9122.54 (19)C34—C33—H33120.3
C11—C10—H10118.7C32—C33—H33120.3
C9—C10—H10118.7C33—C34—C29121.8 (2)
C10—C11—C12116.61 (18)C33—C34—O3117.58 (19)
C10—C11—C19119.47 (18)C29—C34—O3120.5 (2)
C12—C11—C19123.90 (18)C36—C35—C40122.08 (19)
C7—C12—O4118.00 (17)C36—C35—O5119.21 (19)
C7—C12—C11121.21 (19)C40—C35—O5118.60 (18)
O4—C12—C11120.78 (17)C35—C36—C37119.5 (2)
C16—C13—C2111.91 (19)C35—C36—H36120.2
C16—C13—C14106.5 (2)C37—C36—H36120.2
C2—C13—C14109.85 (18)C38—C37—C36119.5 (2)
C16—C13—C15107.6 (2)C38—C37—H37120.3
C2—C13—C15109.0 (2)C36—C37—H37120.3
C14—C13—C15112.01 (19)C39—C38—C37120.5 (2)
C13—C14—H14A109.5C39—C38—H38119.8
C13—C14—H14B109.5C37—C38—H38119.8
H14A—C14—H14B109.5C38—C39—C40120.9 (2)
C13—C14—H14C109.5C38—C39—H39119.5
H14A—C14—H14C109.5C40—C39—H39119.5
H14B—C14—H14C109.5C35—C40—C39117.6 (2)
C13—C15—H15A109.5C35—C40—C41121.36 (18)
C13—C15—H15B109.5C39—C40—C41121.0 (2)
H15A—C15—H15B109.5C42—C41—C46117.6 (2)
C13—C15—H15C109.5C42—C41—C40120.90 (19)
H15A—C15—H15C109.5C46—C41—C40121.5 (2)
H15B—C15—H15C109.5C43—C42—C41121.4 (2)
C13—C16—H16A109.5C43—C42—H42119.3
C13—C16—H16B109.5C41—C42—H42119.3
H16A—C16—H16B109.5C42—C43—C44119.8 (2)
C13—C16—H16C109.5C42—C43—H43120.1
H16A—C16—H16C109.5C44—C43—H43120.1
H16B—C16—H16C109.5C45—C44—C43120.2 (2)
O7—C17—H17A109.5C45—C44—H44119.9
O7—C17—H17B109.5C43—C44—H44119.9
H17A—C17—H17B109.5C44—C45—C46119.6 (2)
O7—C17—H17C109.5C44—C45—H45120.2
H17A—C17—H17C109.5C46—C45—H45120.2
H17B—C17—H17C109.5C45—C46—O6118.40 (19)
O8—C18—H18A109.5C45—C46—C41121.4 (2)
O8—C18—H18B109.5O6—C46—C41119.96 (18)
H18A—C18—H18B109.5C52—C47—C48120.5 (3)
O8—C18—H18C109.5C52—C47—H47119.7
H18A—C18—H18C109.5C48—C47—H47119.7
H18B—C18—H18C109.5C47—C48—C49120.1 (3)
C22—C19—C21106.76 (17)C47—C48—H48119.9
C22—C19—C20110.18 (17)C49—C48—H48119.9
C21—C19—C20107.29 (17)C48—C49—C50119.6 (3)
C22—C19—C11111.34 (16)C48—C49—H49120.2
C21—C19—C11111.70 (17)C50—C49—H49120.2
C20—C19—C11109.46 (16)C49—C50—C51119.9 (3)
C19—C20—H20A109.5C49—C50—H50120.1
C19—C20—H20B109.5C51—C50—H50120.1
H20A—C20—H20B109.5C52—C51—C50120.2 (3)
C19—C20—H20C109.5C52—C51—H51119.9
H20A—C20—H20C109.5C50—C51—H51119.9
H20B—C20—H20C109.5C47—C52—C51119.7 (3)
C19—C21—H21A109.5C47—C52—H52120.2
C19—C21—H21B109.5C51—C52—H52120.2
H21A—C21—H21B109.5C1—O1—P1120.65 (13)
C19—C21—H21C109.5C23—O2—P1119.44 (12)
H21A—C21—H21C109.5C34—O3—P1125.54 (12)
H21B—C21—H21C109.5C12—O4—P2116.93 (12)
C19—C22—H22A109.5C35—O5—P2115.87 (12)
C19—C22—H22B109.5C46—O6—P2125.57 (12)
H22A—C22—H22B109.5C4—O7—C17116.87 (18)
C19—C22—H22C109.5C9—O8—C18115.57 (17)
H22A—C22—H22C109.5O3—P1—O1102.27 (8)
H22B—C22—H22C109.5O3—P1—O299.42 (8)
C24—C23—O2118.85 (19)O1—P1—O293.84 (7)
C24—C23—C28122.4 (2)O6—P2—O4102.43 (8)
O2—C23—C28118.5 (2)O6—P2—O599.14 (8)
C23—C24—C25119.1 (2)O4—P2—O595.73 (7)
C6—C1—C2—C34.9 (3)C31—C32—C33—C341.3 (3)
O1—C1—C2—C3178.35 (17)C32—C33—C34—C293.6 (3)
C6—C1—C2—C13174.64 (19)C32—C33—C34—O3179.15 (17)
O1—C1—C2—C132.1 (3)C30—C29—C34—C333.1 (3)
C1—C2—C3—C40.3 (3)C28—C29—C34—C33176.17 (18)
C13—C2—C3—C4179.2 (2)C30—C29—C34—O3178.52 (16)
C2—C3—C4—O7178.8 (2)C28—C29—C34—O30.8 (3)
C2—C3—C4—C53.3 (3)C40—C35—C36—C370.5 (3)
O7—C4—C5—C6179.9 (2)O5—C35—C36—C37175.6 (2)
C3—C4—C5—C62.5 (3)C35—C36—C37—C380.2 (4)
C2—C1—C6—C55.7 (3)C36—C37—C38—C390.6 (4)
O1—C1—C6—C5177.48 (17)C37—C38—C39—C400.5 (3)
C2—C1—C6—C7175.04 (18)C36—C35—C40—C390.6 (3)
O1—C1—C6—C71.7 (3)O5—C35—C40—C39175.47 (17)
C4—C5—C6—C11.9 (3)C36—C35—C40—C41178.2 (2)
C4—C5—C6—C7178.85 (18)O5—C35—C40—C412.1 (3)
C1—C6—C7—C8117.3 (2)C38—C39—C40—C350.1 (3)
C5—C6—C7—C861.9 (2)C38—C39—C40—C41177.74 (19)
C1—C6—C7—C1266.1 (3)C35—C40—C41—C42136.9 (2)
C5—C6—C7—C12114.7 (2)C39—C40—C41—C4240.6 (3)
C12—C7—C8—C91.6 (3)C35—C40—C41—C4642.9 (3)
C6—C7—C8—C9178.23 (17)C39—C40—C41—C46139.6 (2)
C7—C8—C9—O8175.82 (17)C46—C41—C42—C430.9 (3)
C7—C8—C9—C104.7 (3)C40—C41—C42—C43178.84 (18)
O8—C9—C10—C11174.68 (17)C41—C42—C43—C440.1 (3)
C8—C9—C10—C115.8 (3)C42—C43—C44—C451.4 (3)
C9—C10—C11—C120.4 (3)C43—C44—C45—C461.7 (3)
C9—C10—C11—C19177.90 (17)C44—C45—C46—O6175.18 (17)
C8—C7—C12—O4173.19 (16)C44—C45—C46—C410.6 (3)
C6—C7—C12—O43.3 (3)C42—C41—C46—C450.6 (3)
C8—C7—C12—C117.1 (3)C40—C41—C46—C45179.11 (17)
C6—C7—C12—C11176.38 (17)C42—C41—C46—O6173.83 (16)
C10—C11—C12—C76.0 (3)C40—C41—C46—O66.4 (3)
C19—C11—C12—C7175.73 (17)C52—C47—C48—C490.5 (4)
C10—C11—C12—O4174.29 (16)C47—C48—C49—C500.1 (4)
C19—C11—C12—O43.9 (3)C48—C49—C50—C510.5 (4)
C3—C2—C13—C168.9 (3)C49—C50—C51—C520.5 (4)
C1—C2—C13—C16170.6 (2)C48—C47—C52—C510.6 (4)
C3—C2—C13—C14126.9 (2)C50—C51—C52—C470.1 (4)
C1—C2—C13—C1452.6 (3)C6—C1—O1—P163.9 (2)
C3—C2—C13—C15110.0 (2)C2—C1—O1—P1119.26 (17)
C1—C2—C13—C1570.5 (3)C24—C23—O2—P1105.80 (19)
C10—C11—C19—C22133.04 (19)C28—C23—O2—P179.4 (2)
C12—C11—C19—C2248.8 (2)C33—C34—O3—P1116.70 (17)
C10—C11—C19—C2113.8 (2)C29—C34—O3—P167.7 (2)
C12—C11—C19—C21168.04 (18)C7—C12—O4—P266.19 (19)
C10—C11—C19—C20104.9 (2)C11—C12—O4—P2114.13 (17)
C12—C11—C19—C2073.3 (2)C36—C35—O5—P2102.7 (2)
O2—C23—C24—C25175.12 (19)C40—C35—O5—P281.1 (2)
C28—C23—C24—C250.5 (3)C45—C46—O6—P2116.01 (18)
C23—C24—C25—C260.5 (3)C41—C46—O6—P269.4 (2)
C24—C25—C26—C270.1 (4)C5—C4—O7—C171.9 (3)
C25—C26—C27—C280.6 (3)C3—C4—O7—C17175.8 (2)
C24—C23—C28—C270.0 (3)C8—C9—O8—C1814.4 (3)
O2—C23—C28—C27174.62 (17)C10—C9—O8—C18166.10 (17)
C24—C23—C28—C29178.94 (19)C34—O3—P1—O159.05 (17)
O2—C23—C28—C294.3 (3)C34—O3—P1—O237.00 (17)
C26—C27—C28—C230.6 (3)C1—O1—P1—O3134.20 (14)
C26—C27—C28—C29179.5 (2)C1—O1—P1—O2125.29 (14)
C23—C28—C29—C3443.9 (3)C23—O2—P1—O353.57 (17)
C27—C28—C29—C34137.1 (2)C23—O2—P1—O1156.69 (16)
C23—C28—C29—C30136.8 (2)C46—O6—P2—O466.92 (16)
C27—C28—C29—C3042.1 (3)C46—O6—P2—O531.07 (17)
C34—C29—C30—C310.4 (3)C12—O4—P2—O6131.10 (13)
C28—C29—C30—C31178.94 (19)C12—O4—P2—O5128.21 (13)
C29—C30—C31—C321.9 (3)C35—O5—P2—O660.03 (15)
C30—C31—C32—C331.4 (3)C35—O5—P2—O4163.63 (14)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C47–C52 benzene ring.
D—H···AD—HH···AD···AD—H···A
C39—H39···Cg1i0.952.753.678 (3)165
Symmetry code: (i) x, y1, z.
 

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First citationMeyer, T. G., Fischer, A., Jones, P. G. & Schmutzler, R. (1993). Z. Naturforsch. B, 48, 659–671.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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