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Crystal structure of the 4 + 2 cyclo­adduct of photooxidized anthracene and C60 fullerene

aWigner Research Centre for Physics of the Hungarian Academy of Sciences, POB 49, Budapest, H-1525, Hungary, and bRejtő Sándor Faculty of Light Industry and Environmental Engineering, Óbuda University Doberdó út 6, Budapest, H-1034, Hungary
*Correspondence e-mail: bortel.gabor@wigner.mta.hu

Edited by P. Bombicz, Hungarian Academy of Sciences, Hungary (Received 24 July 2014; accepted 30 August 2014; online 31 October 2014)

The structure of the title compound, 5,6-[(1R,10S)-2,9-dioxatri­cyclo­[8.6.03,8.011,16]hexa­decane-1,10-di­yl]-(C60–Ih)[5,6]fullerene methane­dithione 0.1-solvate, C74H10O2·0.1CS2, has tetra­gonal (P42/n) symmetry at 100 K. It has a unique eight-membered ring, with two incorporated O atoms in place of the original central ring of the anthracene. The distortion of the mol­ecular geometry around the cyclo­adduct bonds corresponds to that seen in related fullerene derivatives. Close packing of the adduct forms cavities partially filled with disordered carbon di­sulfide solvent mol­ecule. The 41% occupancy of the cavities yields an overall 1:0.103 adduct–solvent ratio. Reaction steps are described as light-assisted singlet-oxygen generation, peroxide, epoxide and dioxocin derivative formation and the final step of thermally activated cyclo­addition.

1. Chemical context

The first step of the formation of C60(C14H10O2) is the generation of singlet oxygen by the photo-excited C60. Singlet oxygen reacts with anthracene via several consecutive reactions, similarly to the mechanism described previously by Rigaudy et al. (1978[Rigaudy, J., Breliere, C. & Scribe, P. (1978). Tetrahedron Lett. 7, 687-690.]). The addition of singlet oxygen to anthracene results in a highly reactive 9,10-endoperoxide. The thermal rearrangement of the peroxide results in diepoxide, and after a ring extension reaction the final inter­mediare, a [1,4]-dioxocin derivative forms. This inter­mediary reacts with C60, forming the product via a thermal (4 + 2) cyclo­addition. The cyclo­addition is irreversible because the reverse reaction, the formation of the dioxocin derivative, is energetically unfavourable.

[Scheme 1]

2. Structural commentary

The adduct, shows a unique eight-membered ring with two incorporated O atoms. A displacement ellipsoid plot is shown in Fig. 1[link]. The bond lengths and angles around the strongly distorted bonding region are shown in Figs. 2[link] and 3[link].

[Figure 1]
Figure 1
Thermal ellipsoid plot of the cyclo­adduct as a result of unrestrained anisotropic refinement and the disordered solvent.
[Figure 2]
Figure 2
Refined bond lengths around the bonding region of the cyclo­adduct.
[Figure 3]
Figure 3
Refined bond angles of the bonding carbon and oxygen atoms.

3. Supra­molecular features

The 10 Å center-to-center distance of the fullerene cages shown in Fig. 4[link] indicates a locally realized close packing despite the ligands. The disordered CS2 solvent mol­ecules occupy the large cavities between the fullerene adducts, as shown in Fig. 5[link].

[Figure 4]
Figure 4
Locally close-packed arrangements of fullerene cages as generated by the 42 screw axis.
[Figure 5]
Figure 5
The disordered CS2 solvent on a [\overline{4}] rotoinversion axis surrounded by fullerene cages.

4. Database survey

No similar eight-membered ring as a substructure of a cyclo­adduct was found in database searches. The structure published here was described in a previous study by Bortel et al. (1995[Bortel, G., Oszlányi, G., Faigel, G., Tegze, M., Pusztai, T. & Pekker, S. (1995). Mater. Sci. Forum, 228-231, 879-884.]), but neither the collected data nor the refined coordinates are available in that publication. The current structural data collected at low temperature is of significantly better quality in terms of resolution, statistics and number of reflections. The resulting structure is in agreement with the previously determined one.

5. Synthesis and crystallization

C60(C14H10O2) was prepared by the photo-oxidation of anthracene and the simultaneous cyclo­addition of its oxidized inter­mediary to C60. 144 mg C60 (0.2 mmol) and 214 mg anthracene (1.2 mmol) were dissolved in 150 ml toluene. Oxygen was bubbled through the solution and the reaction mixture was illuminated with a luminescent light source of 23 watt. After a reaction time of 1 h at 313 K, the starting materials and the products were separated by column chromatography in silica stationary phase with hexa­ne/toluene eluent mixtures. The major product was recrystallized from carbon di­sulfide by a slow diffusion of iso­pentane into the solution.

6. Refinement

The structure is described in the standard setting of the tetra­gonal space group P42/n with origin choice 2, origin at inversion center. Least-squares full-matrix refinement on F2 with all atoms treated anisotropically (except the C atom of CS2) and with riding H atoms without any restraints or constraints (except for a restraint on the bond length of CS2) was stable and yielded good figure of merits. The fullerene compound shows no orientational disorder; it is fixed by its attachment. The CS2 solvent shows disorder, that was described with an approximate atomic model. The C atom is located on a [\overline{4}] rotoinversion center (2a Wyckoff position) and the S-atom positions are ensued by the multiplication effect of the [\overline{4}] rotoinversion axis. This simple model could not be significantly improved by introducing additional sites or even by masking the corresponding region. The highest peak (1.02 e Å−3) and deepest hole (−0.74 e Å−3) of the residual electron-density map are located at 0.43 Å from the C and 0.69 Å from the S atom of CS2, respectively. Crystal data, data collection and structure refinement details are summarized in Table 1[link].

Table 1
Experimental details

Crystal data
Chemical formula C74H10O2·0.1(CS2)
Mr 938.68
Crystal system, space group Tetragonal, P42/n
Temperature (K) 100
a, c (Å) 22.66570 (13), 14.24938 (11)
V3) 7320.40 (10)
Z 8
Radiation type Cu Kα
μ (mm−1) 0.91
Crystal size (mm) 0.18 × 0.15 × 0.08
 
Data collection
Diffractometer Agilent SuperNova (Dual, Cu at zero, Atlas)
Absorption correction Multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.])
Tmin, Tmax 0.911, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 35247, 7171, 6473
Rint 0.021
(sin θ/λ)max−1) 0.619
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.120, 1.04
No. of reflections 7171
No. of parameters 696
No. of restraints 7
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.02, −0.74
Computer programs: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Chemical context top

The first step of the formation of C60(C14H10O2) is the generation of singlet oxygen by the photo-excited C60. Singlet oxygen reacts with anthracene via several consecutive reactions, similarly to the mechanism described previously by Rigaudy et al. (1978). The addition of singlet oxygen to anthracene results in a highly reactive 9,10-endoperoxide. The thermal rearrangement of the peroxide results in diepoxide, and after a ring extension reaction the final inter­mediare, a [1,4]-dioxocin derivative forms. This inter­mediary reacts with C60, forming the product via a thermal (4+2) cyclo­addition. The cyclo­addition is irreversible because the reverse reaction, the formation of the dioxocin derivative, is energetically unfavourable.

Structural commentary top

The adduct, shows a unique eight-membered ring with two incorporated O atoms. A displacement ellipsoid plot is shown in Fig. 1. The bond lengths and angles around the strongly distorted bonding region are shown in Figs. 2 and 3.

Supra­molecular features top

The 10 Å center-to-center distance of the fullerene cages shown in Fig. 4 indicates a locally realized close packing despite the ligands. The disordered CS2 solvent molecules occupy the large cavities between the fullerene adducts, as shown in Fig. 5.

Database survey top

No similar eight-membered ring as a substructure of a cyclo­adduct was found in database searches. The structure published here was described in a previous study by Bortel et al. (1995), but neither the collected data nor the refined coordinates are available in that publication. The current structural data collected at low temperature is of significantly better quality in terms of resolution, statistics and number of reflections. The resulting structure is in agreement with the previously determined one.

Synthesis and crystallization top

C60(C14H10O2) was prepared by the photo-oxidation of anthracene and the simultaneous cyclo­addition of its oxidized inter­mediary to C60. 144 mg C60 (0.2 mmol) and 214 mg anthracene (1.2 mmol) were dissolved in 150 ml toluene. Oxygen was bubbled through the solution and the reaction mixture was illuminated with a luminescent light source of 23 watt. After a reaction time of 1 h at 313 K, the starting materials and the products were separated by column chromatography in silica stationary phase with hexane/toluene eluent mixtures. The major product was recrystallized from carbon di­sulfide by a slow diffusion of iso­pentane into the solution.

Refinement top

The structure is described in the standard setting of the tetra­gonal space group P42/n with origin choice 2, origin at inversion center. Least-squares full-matrix refinement on F2 with all atoms treated anisotropically (except the C atom of CS2) and with riding H atoms without any restraints or constraints (except for a restraint on the bond length of CS2) was stable and yielded good figure of merits. The fullerene compound shows no orientational disorder; it is fixed by its attachment. The CS2 solvent shows disorder, that was described with an approximate atomic model. The C atom is located on a 4 rotoinversion center (2a Wyckoff position) and the S-atom positions are ensued by the multiplication effect of the 4 rotoinversion axis. This simple model could not be significantly improved by introducing additional sites or even by masking the corresponding region. The highest peak (1.02 e Å-3) and deepest hole (-0.74 e Å-3) of the residual electron-density map are located at 0.43 Å from the C and 0.69 Å from the S atom of CS2, respectively. Crystal data, data collection and structure refinement details are summarized in Table 1.

Related literature top

The structure published here was described in a previous study by Bortel et al. (1995), but neither the collected data nor the refined coordinates are available in that publication. Current structural data collected at low temperature is of significantly better quality in terms of resolution, statistics and number of reflections. The resulting structure is in agreement with the previously determined one. For related literature on photooxidation of anthracene, see: Rigaudy et al. (1978).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Olex2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
Fig. 1 Thermal ellipsoid plot of the cycloadduct as a result of unrestrained anisotropic refinement and the disordered solvent.

Fig. 2 Refined bond lengths around the bonding region of the cycloadduct.

Fig. 3 Refined bond angles of the bonding carbon and oxygen atoms.

Fig. 4 Locally close-packed arrangements of fullerene cages as generated by the 42 screw axis.

Fig. 5 The disordered CS2 solvent on a 4 rotoinversion axis surrounded by fullerene cages.
5,6-[(1R,10S)-2,9-Dioxatricyclo[8.6.03,8.011,16]hexadecane-1,10-diyl]-(C60–Ih)[5,6]fullerene methanedithione 0.1-solvate top
Crystal data top
C74H10O2·0.1(CS2)Dx = 1.703 Mg m3
Mr = 938.68Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P42/nCell parameters from 18450 reflections
a = 22.66570 (13) Åθ = 3.7–72.5°
c = 14.24938 (11) ŵ = 0.91 mm1
V = 7320.40 (10) Å3T = 100 K
Z = 8Irregular, metallic dark black
F(000) = 37910.18 × 0.15 × 0.08 mm
Data collection top
Agilent SuperNova (Dual, Cu at zero, Atlas)
diffractometer
7171 independent reflections
Radiation source: sealed X-ray tube, Agilent SuperNova (Cu) X-ray Source6473 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.021
Detector resolution: 10.5908 pixels mm-1θmax = 72.6°, θmin = 3.7°
ω scansh = 2723
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 2627
Tmin = 0.911, Tmax = 1.000l = 1717
35247 measured reflections
Refinement top
Refinement on F27 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.059P)2 + 7.0685P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.003
7171 reflectionsΔρmax = 1.02 e Å3
696 parametersΔρmin = 0.74 e Å3
Crystal data top
C74H10O2·0.1(CS2)Z = 8
Mr = 938.68Cu Kα radiation
Tetragonal, P42/nµ = 0.91 mm1
a = 22.66570 (13) ÅT = 100 K
c = 14.24938 (11) Å0.18 × 0.15 × 0.08 mm
V = 7320.40 (10) Å3
Data collection top
Agilent SuperNova (Dual, Cu at zero, Atlas)
diffractometer
7171 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
6473 reflections with I > 2σ(I)
Tmin = 0.911, Tmax = 1.000Rint = 0.021
35247 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0457 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.04Δρmax = 1.02 e Å3
7171 reflectionsΔρmin = 0.74 e Å3
696 parameters
Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.47684 (5)0.26998 (5)0.76855 (8)0.0210 (3)
O20.37450 (5)0.21977 (6)0.70586 (9)0.0236 (3)
C10.41761 (7)0.21747 (8)0.52192 (12)0.0186 (3)
C20.39498 (7)0.17973 (8)0.44940 (12)0.0210 (4)
C30.41989 (8)0.12155 (8)0.46178 (12)0.0214 (4)
C40.45846 (7)0.12302 (7)0.54174 (11)0.0182 (3)
C50.44903 (7)0.18069 (7)0.59712 (12)0.0176 (3)
C60.50889 (7)0.20944 (7)0.63493 (11)0.0170 (3)
C70.52439 (7)0.26867 (7)0.58922 (11)0.0173 (3)
C80.48633 (8)0.30127 (7)0.53539 (12)0.0199 (3)
C90.43107 (7)0.27483 (8)0.50045 (12)0.0202 (3)
C100.42135 (8)0.29740 (8)0.40675 (13)0.0228 (4)
C110.39726 (8)0.26139 (8)0.33720 (13)0.0237 (4)
C120.38361 (7)0.20102 (9)0.35913 (13)0.0231 (4)
C130.39789 (8)0.16487 (9)0.27781 (12)0.0243 (4)
C140.42198 (8)0.10914 (8)0.28984 (13)0.0241 (4)
C150.43265 (8)0.08647 (8)0.38387 (13)0.0231 (4)
C160.48650 (9)0.05306 (7)0.38194 (13)0.0238 (4)
C170.52473 (8)0.05630 (7)0.45803 (12)0.0224 (4)
C180.50991 (8)0.09155 (7)0.53941 (12)0.0196 (3)
C190.56514 (8)0.11783 (7)0.57495 (12)0.0190 (3)
C200.56485 (7)0.17411 (7)0.60967 (11)0.0172 (3)
C210.61153 (7)0.21378 (8)0.58438 (11)0.0189 (3)
C220.58652 (8)0.27171 (8)0.57148 (12)0.0193 (3)
C230.60939 (8)0.30951 (7)0.50312 (12)0.0214 (4)
C240.56960 (8)0.34410 (7)0.44709 (13)0.0225 (4)
C250.50913 (8)0.33943 (7)0.46232 (12)0.0217 (4)
C260.46911 (8)0.33716 (7)0.38330 (13)0.0235 (4)
C270.49131 (9)0.33936 (7)0.29218 (13)0.0239 (4)
C280.46652 (8)0.30130 (8)0.22011 (12)0.0241 (4)
C290.42054 (8)0.26311 (8)0.24215 (12)0.0236 (4)
C300.42074 (8)0.20356 (9)0.20566 (13)0.0241 (4)
C310.46680 (8)0.18459 (8)0.14784 (12)0.0228 (4)
C320.49167 (8)0.12613 (8)0.16037 (12)0.0233 (4)
C330.46960 (9)0.08919 (8)0.23020 (13)0.0246 (4)
C340.50983 (9)0.05453 (7)0.28705 (12)0.0245 (4)
C350.57045 (9)0.05839 (7)0.27278 (13)0.0241 (4)
C360.61016 (8)0.06080 (8)0.35200 (13)0.0243 (4)
C370.58764 (8)0.05989 (7)0.44316 (13)0.0233 (4)
C380.61245 (8)0.09803 (8)0.51441 (12)0.0219 (4)
C390.65876 (8)0.13586 (8)0.49194 (12)0.0224 (4)
C400.65853 (7)0.19521 (8)0.52785 (12)0.0214 (4)
C410.68151 (7)0.23398 (8)0.45576 (12)0.0225 (4)
C420.65757 (8)0.28997 (8)0.44387 (12)0.0225 (4)
C430.64713 (8)0.31269 (8)0.35002 (13)0.0229 (4)
C440.59253 (9)0.34602 (7)0.35189 (13)0.0236 (4)
C450.55400 (9)0.34376 (7)0.27635 (13)0.0236 (4)
C460.56838 (8)0.30786 (8)0.19542 (12)0.0223 (4)
C470.51416 (8)0.28177 (8)0.16034 (12)0.0224 (4)
C480.51437 (8)0.22467 (8)0.12478 (12)0.0221 (4)
C490.56890 (8)0.19109 (8)0.12280 (11)0.0212 (4)
C500.55485 (8)0.13015 (8)0.14525 (12)0.0221 (4)
C510.59350 (8)0.09695 (8)0.20039 (12)0.0232 (4)
C520.64747 (8)0.12325 (8)0.23528 (12)0.0231 (4)
C530.65811 (8)0.10066 (8)0.32865 (13)0.0243 (4)
C540.68191 (8)0.13741 (8)0.39706 (13)0.0239 (4)
C550.69592 (7)0.19815 (9)0.37493 (12)0.0232 (4)
C560.68558 (7)0.21988 (8)0.28473 (12)0.0230 (4)
C570.66067 (8)0.27823 (8)0.27212 (12)0.0227 (4)
C580.62057 (8)0.27587 (8)0.19319 (12)0.0219 (4)
C590.62078 (8)0.21610 (8)0.15649 (12)0.0207 (4)
C600.66083 (8)0.18159 (8)0.21354 (12)0.0218 (4)
C610.40505 (7)0.16593 (7)0.67817 (12)0.0187 (3)
H610.37550.13840.65340.022*
C620.43589 (7)0.13605 (7)0.75835 (12)0.0182 (3)
C630.41356 (8)0.08552 (8)0.80094 (12)0.0210 (4)
H630.37890.06820.77930.025*
C640.44410 (8)0.06119 (8)0.87681 (12)0.0232 (4)
H640.42990.02690.90480.028*
C650.49495 (8)0.08705 (8)0.91104 (12)0.0237 (4)
H650.51450.07050.96200.028*
C660.51678 (7)0.13810 (8)0.86890 (12)0.0200 (3)
H660.55070.15600.89210.024*
C670.48766 (7)0.16222 (7)0.79198 (11)0.0175 (3)
C680.50944 (7)0.21694 (7)0.74399 (12)0.0178 (3)
H680.55050.22300.76320.021*
C690.43034 (8)0.26278 (7)0.83043 (12)0.0197 (3)
C700.43566 (8)0.28222 (7)0.92241 (12)0.0193 (3)
H700.47020.30010.94310.023*
C710.38791 (8)0.27441 (8)0.98321 (13)0.0252 (4)
H710.39080.28711.04510.030*
C720.33624 (9)0.24787 (9)0.95206 (14)0.0293 (4)
H720.30480.24280.99330.035*
C730.33118 (8)0.22874 (9)0.85896 (14)0.0264 (4)
H730.29660.21100.83800.032*
C740.37838 (8)0.23669 (8)0.79852 (12)0.0215 (4)
S10.2763 (3)0.2431 (3)0.1529 (6)0.264 (6)0.206 (3)
C750.25000.25000.25000.022 (2)*0.413 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0251 (6)0.0179 (6)0.0199 (6)0.0006 (5)0.0040 (5)0.0009 (5)
O20.0226 (6)0.0271 (7)0.0210 (6)0.0059 (5)0.0028 (5)0.0026 (5)
C10.0129 (7)0.0264 (9)0.0165 (8)0.0013 (6)0.0021 (6)0.0008 (7)
C20.0124 (7)0.0308 (9)0.0198 (8)0.0047 (7)0.0007 (6)0.0008 (7)
C30.0184 (8)0.0259 (9)0.0201 (8)0.0118 (7)0.0009 (7)0.0016 (7)
C40.0212 (8)0.0176 (8)0.0157 (8)0.0067 (6)0.0024 (6)0.0021 (6)
C50.0174 (8)0.0191 (8)0.0165 (8)0.0019 (6)0.0001 (6)0.0003 (6)
C60.0176 (8)0.0173 (8)0.0162 (8)0.0011 (6)0.0010 (6)0.0000 (6)
C70.0221 (8)0.0166 (8)0.0131 (7)0.0031 (6)0.0014 (6)0.0044 (6)
C80.0262 (9)0.0143 (8)0.0190 (8)0.0027 (6)0.0041 (7)0.0035 (6)
C90.0187 (8)0.0219 (8)0.0199 (8)0.0073 (7)0.0022 (6)0.0010 (7)
C100.0211 (8)0.0236 (9)0.0238 (9)0.0100 (7)0.0011 (7)0.0030 (7)
C110.0162 (8)0.0319 (10)0.0230 (9)0.0075 (7)0.0031 (7)0.0040 (7)
C120.0121 (8)0.0351 (10)0.0221 (9)0.0020 (7)0.0030 (6)0.0011 (7)
C130.0162 (8)0.0376 (10)0.0192 (8)0.0081 (7)0.0061 (7)0.0002 (7)
C140.0231 (9)0.0276 (9)0.0215 (9)0.0141 (7)0.0028 (7)0.0040 (7)
C150.0245 (9)0.0217 (8)0.0231 (9)0.0148 (7)0.0003 (7)0.0022 (7)
C160.0367 (10)0.0122 (8)0.0226 (9)0.0089 (7)0.0031 (7)0.0010 (6)
C170.0356 (10)0.0105 (7)0.0211 (8)0.0015 (7)0.0038 (7)0.0038 (6)
C180.0274 (9)0.0138 (7)0.0175 (8)0.0029 (6)0.0010 (7)0.0047 (6)
C190.0222 (8)0.0193 (8)0.0154 (8)0.0036 (6)0.0012 (6)0.0063 (6)
C200.0166 (8)0.0227 (8)0.0123 (7)0.0003 (6)0.0026 (6)0.0018 (6)
C210.0175 (8)0.0258 (9)0.0133 (7)0.0028 (6)0.0053 (6)0.0004 (6)
C220.0213 (8)0.0218 (8)0.0147 (8)0.0061 (6)0.0019 (6)0.0050 (6)
C230.0255 (9)0.0193 (8)0.0194 (8)0.0104 (7)0.0009 (7)0.0043 (7)
C240.0330 (10)0.0117 (7)0.0227 (9)0.0065 (7)0.0021 (7)0.0032 (6)
C250.0334 (10)0.0111 (7)0.0207 (8)0.0034 (7)0.0037 (7)0.0020 (6)
C260.0297 (9)0.0141 (8)0.0265 (9)0.0084 (7)0.0019 (7)0.0030 (7)
C270.0335 (10)0.0147 (8)0.0236 (9)0.0066 (7)0.0011 (7)0.0065 (7)
C280.0293 (9)0.0236 (9)0.0195 (8)0.0079 (7)0.0028 (7)0.0078 (7)
C290.0206 (8)0.0313 (10)0.0190 (8)0.0061 (7)0.0064 (7)0.0049 (7)
C300.0184 (8)0.0351 (10)0.0188 (8)0.0023 (7)0.0078 (7)0.0020 (7)
C310.0250 (9)0.0309 (9)0.0125 (7)0.0046 (7)0.0059 (7)0.0004 (7)
C320.0292 (9)0.0269 (9)0.0137 (8)0.0069 (7)0.0018 (7)0.0055 (7)
C330.0323 (10)0.0228 (9)0.0188 (8)0.0120 (7)0.0027 (7)0.0063 (7)
C340.0396 (11)0.0132 (8)0.0207 (9)0.0069 (7)0.0022 (8)0.0051 (6)
C350.0392 (10)0.0120 (8)0.0212 (8)0.0030 (7)0.0048 (8)0.0043 (6)
C360.0322 (10)0.0144 (8)0.0264 (9)0.0094 (7)0.0051 (8)0.0006 (7)
C370.0327 (10)0.0133 (8)0.0240 (9)0.0076 (7)0.0029 (7)0.0039 (7)
C380.0255 (9)0.0215 (8)0.0186 (8)0.0096 (7)0.0013 (7)0.0056 (7)
C390.0176 (8)0.0308 (9)0.0190 (8)0.0082 (7)0.0022 (7)0.0041 (7)
C400.0139 (8)0.0332 (10)0.0172 (8)0.0005 (7)0.0050 (6)0.0020 (7)
C410.0126 (8)0.0351 (10)0.0197 (8)0.0061 (7)0.0020 (6)0.0008 (7)
C420.0190 (8)0.0277 (9)0.0207 (8)0.0127 (7)0.0015 (7)0.0032 (7)
C430.0240 (9)0.0215 (8)0.0233 (9)0.0134 (7)0.0030 (7)0.0005 (7)
C440.0334 (10)0.0137 (8)0.0239 (9)0.0090 (7)0.0040 (7)0.0008 (7)
C450.0365 (10)0.0126 (8)0.0217 (9)0.0026 (7)0.0040 (7)0.0054 (6)
C460.0320 (10)0.0181 (8)0.0166 (8)0.0028 (7)0.0020 (7)0.0069 (6)
C470.0274 (9)0.0251 (9)0.0148 (8)0.0021 (7)0.0018 (7)0.0088 (7)
C480.0259 (9)0.0284 (9)0.0120 (8)0.0016 (7)0.0037 (6)0.0034 (7)
C490.0272 (9)0.0246 (9)0.0119 (7)0.0019 (7)0.0025 (6)0.0012 (6)
C500.0305 (9)0.0222 (9)0.0135 (8)0.0034 (7)0.0027 (7)0.0051 (6)
C510.0323 (10)0.0192 (8)0.0181 (8)0.0016 (7)0.0068 (7)0.0059 (7)
C520.0237 (9)0.0261 (9)0.0194 (8)0.0086 (7)0.0066 (7)0.0019 (7)
C530.0239 (9)0.0245 (9)0.0243 (9)0.0105 (7)0.0054 (7)0.0010 (7)
C540.0156 (8)0.0316 (10)0.0243 (9)0.0084 (7)0.0015 (7)0.0021 (7)
C550.0120 (8)0.0354 (10)0.0223 (9)0.0001 (7)0.0014 (6)0.0000 (7)
C560.0149 (8)0.0318 (10)0.0223 (9)0.0042 (7)0.0051 (7)0.0003 (7)
C570.0206 (8)0.0279 (9)0.0195 (8)0.0112 (7)0.0037 (7)0.0031 (7)
C580.0258 (9)0.0232 (9)0.0166 (8)0.0066 (7)0.0048 (7)0.0048 (7)
C590.0240 (9)0.0244 (9)0.0137 (8)0.0015 (7)0.0064 (6)0.0018 (6)
C600.0185 (8)0.0304 (9)0.0166 (8)0.0009 (7)0.0056 (6)0.0014 (7)
C610.0163 (8)0.0209 (8)0.0188 (8)0.0024 (6)0.0009 (6)0.0014 (6)
C620.0184 (8)0.0197 (8)0.0165 (8)0.0001 (6)0.0039 (6)0.0023 (6)
C630.0249 (9)0.0193 (8)0.0189 (8)0.0029 (7)0.0033 (7)0.0023 (7)
C640.0281 (9)0.0202 (8)0.0214 (9)0.0007 (7)0.0070 (7)0.0018 (7)
C650.0262 (9)0.0273 (9)0.0178 (8)0.0062 (7)0.0015 (7)0.0020 (7)
C660.0175 (8)0.0254 (9)0.0171 (8)0.0030 (6)0.0017 (6)0.0022 (7)
C670.0177 (8)0.0191 (8)0.0156 (8)0.0017 (6)0.0032 (6)0.0020 (6)
C680.0172 (8)0.0199 (8)0.0164 (8)0.0004 (6)0.0008 (6)0.0016 (6)
C690.0225 (8)0.0164 (8)0.0201 (8)0.0038 (6)0.0031 (7)0.0008 (6)
C700.0227 (8)0.0167 (8)0.0184 (8)0.0054 (6)0.0020 (7)0.0002 (6)
C710.0316 (10)0.0248 (9)0.0192 (8)0.0078 (7)0.0021 (7)0.0027 (7)
C720.0255 (9)0.0347 (10)0.0278 (10)0.0073 (8)0.0082 (8)0.0030 (8)
C730.0182 (8)0.0302 (10)0.0309 (10)0.0045 (7)0.0003 (7)0.0034 (8)
C740.0231 (9)0.0220 (8)0.0193 (8)0.0068 (7)0.0011 (7)0.0010 (7)
S10.210 (8)0.061 (4)0.522 (14)0.049 (5)0.292 (9)0.082 (7)
Geometric parameters (Å, º) top
O1—C681.454 (2)C32—C331.393 (3)
O1—C691.384 (2)C32—C501.451 (3)
O2—C611.458 (2)C33—C341.451 (3)
O2—C741.378 (2)C34—C351.392 (3)
C1—C21.436 (2)C35—C361.445 (3)
C1—C51.533 (2)C35—C511.449 (2)
C1—C91.370 (2)C36—C371.396 (3)
C2—C31.445 (3)C36—C531.452 (3)
C2—C121.398 (2)C37—C381.447 (3)
C3—C41.437 (2)C38—C391.393 (3)
C3—C151.396 (3)C39—C401.439 (3)
C4—C51.542 (2)C39—C541.451 (2)
C4—C181.368 (2)C40—C411.449 (2)
C5—C61.599 (2)C41—C421.391 (3)
C5—C611.562 (2)C41—C551.447 (3)
C6—C71.533 (2)C42—C431.452 (3)
C6—C201.543 (2)C43—C441.450 (3)
C6—C681.563 (2)C43—C571.391 (3)
C7—C81.371 (2)C44—C451.387 (3)
C7—C221.432 (2)C45—C461.449 (3)
C8—C91.475 (2)C46—C471.453 (3)
C8—C251.449 (2)C46—C581.388 (3)
C9—C101.447 (2)C47—C481.390 (3)
C10—C111.395 (3)C48—C491.452 (3)
C10—C261.448 (3)C49—C501.453 (2)
C11—C121.437 (3)C49—C591.391 (3)
C11—C291.454 (3)C50—C511.397 (3)
C12—C131.456 (3)C51—C521.449 (3)
C13—C141.387 (3)C52—C531.446 (3)
C13—C301.447 (3)C52—C601.391 (3)
C14—C151.455 (3)C53—C541.391 (3)
C14—C331.446 (3)C54—C551.448 (3)
C15—C161.437 (3)C55—C561.396 (3)
C16—C171.390 (3)C56—C571.449 (3)
C16—C341.452 (2)C56—C601.448 (3)
C17—C181.448 (2)C57—C581.447 (3)
C17—C371.444 (3)C58—C591.452 (2)
C18—C191.476 (2)C59—C601.448 (3)
C19—C201.368 (2)C61—C621.501 (2)
C19—C381.448 (2)C62—C631.392 (2)
C20—C211.434 (2)C62—C671.400 (2)
C21—C221.442 (2)C63—C641.397 (3)
C21—C401.400 (2)C64—C651.382 (3)
C22—C231.397 (2)C65—C661.394 (3)
C23—C241.437 (3)C66—C671.391 (2)
C23—C421.450 (3)C67—C681.500 (2)
C24—C251.392 (3)C69—C701.388 (2)
C24—C441.453 (2)C69—C741.394 (3)
C25—C261.447 (3)C70—C711.397 (3)
C26—C271.393 (3)C71—C721.389 (3)
C27—C281.454 (3)C72—C731.400 (3)
C27—C451.442 (3)C73—C741.385 (3)
C28—C291.391 (3)S1—S1i1.234 (13)
C28—C471.445 (3)S1—C751.514 (9)
C29—C301.446 (3)C75—S1ii1.514 (9)
C30—C311.398 (3)C75—S1iii1.514 (9)
C31—C321.451 (3)C75—S1i1.514 (9)
C31—C481.448 (3)
C69—O1—C68116.28 (12)C34—C35—C51119.86 (17)
C74—O2—C61117.52 (13)C36—C35—C51107.97 (16)
C2—C1—C5110.18 (15)C35—C36—C53108.11 (16)
C9—C1—C2118.95 (16)C37—C36—C35119.92 (17)
C9—C1—C5124.67 (15)C37—C36—C53119.74 (17)
C1—C2—C3108.43 (15)C17—C37—C38108.33 (15)
C12—C2—C1121.49 (16)C36—C37—C17119.90 (17)
C12—C2—C3119.95 (16)C36—C37—C38120.14 (17)
C4—C3—C2108.26 (15)C37—C38—C19108.39 (16)
C15—C3—C2120.25 (16)C39—C38—C19120.29 (16)
C15—C3—C4121.20 (17)C39—C38—C37119.96 (16)
C3—C4—C5109.96 (15)C38—C39—C40119.40 (16)
C18—C4—C3119.18 (16)C38—C39—C54120.12 (17)
C18—C4—C5124.95 (15)C40—C39—C54108.07 (16)
C1—C5—C499.65 (13)C21—C40—C39119.23 (16)
C1—C5—C6114.08 (13)C21—C40—C41119.94 (17)
C1—C5—C61109.69 (13)C39—C40—C41108.27 (15)
C4—C5—C6113.61 (13)C42—C41—C40119.98 (16)
C4—C5—C61106.58 (13)C42—C41—C55120.22 (16)
C61—C5—C6112.32 (13)C55—C41—C40107.77 (16)
C7—C6—C5114.10 (13)C23—C42—C43107.77 (16)
C7—C6—C2099.62 (13)C41—C42—C23120.12 (16)
C7—C6—C68108.99 (13)C41—C42—C43119.96 (16)
C20—C6—C5114.05 (13)C44—C43—C42107.86 (15)
C20—C6—C68106.38 (13)C57—C43—C42119.96 (17)
C68—C6—C5112.71 (13)C57—C43—C44119.69 (17)
C8—C7—C6124.46 (15)C43—C44—C24107.87 (16)
C8—C7—C22119.60 (15)C45—C44—C24119.87 (17)
C22—C7—C6110.02 (14)C45—C44—C43120.25 (16)
C7—C8—C9120.28 (15)C27—C45—C46107.90 (16)
C7—C8—C25119.98 (16)C44—C45—C27120.10 (16)
C25—C8—C9107.62 (15)C44—C45—C46119.79 (17)
C1—C9—C8119.94 (15)C45—C46—C47108.20 (16)
C1—C9—C10120.51 (16)C58—C46—C45120.24 (17)
C10—C9—C8107.29 (15)C58—C46—C47120.04 (16)
C9—C10—C26108.62 (16)C28—C47—C46107.74 (16)
C11—C10—C9120.56 (17)C48—C47—C28120.18 (17)
C11—C10—C26119.53 (17)C48—C47—C46120.11 (16)
C10—C11—C12119.13 (16)C31—C48—C49108.02 (16)
C10—C11—C29120.26 (17)C47—C48—C31119.94 (17)
C12—C11—C29107.82 (16)C47—C48—C49119.89 (16)
C2—C12—C11119.27 (16)C48—C49—C50107.91 (15)
C2—C12—C13119.81 (17)C59—C49—C48119.95 (16)
C11—C12—C13108.36 (16)C59—C49—C50119.79 (16)
C14—C13—C12120.13 (16)C32—C50—C49107.99 (16)
C14—C13—C30119.93 (17)C51—C50—C32120.10 (16)
C30—C13—C12107.70 (16)C51—C50—C49119.89 (16)
C13—C14—C15120.06 (17)C50—C51—C35119.93 (17)
C13—C14—C33120.40 (16)C50—C51—C52120.06 (16)
C33—C14—C15107.85 (17)C52—C51—C35107.96 (16)
C3—C15—C14119.77 (17)C53—C52—C51108.11 (16)
C3—C15—C16119.44 (16)C60—C52—C51119.90 (16)
C16—C15—C14108.04 (16)C60—C52—C53120.35 (17)
C15—C16—C34108.37 (16)C52—C53—C36107.84 (16)
C17—C16—C15119.14 (16)C54—C53—C36120.15 (16)
C17—C16—C34119.87 (17)C54—C53—C52119.83 (17)
C16—C17—C18120.62 (17)C53—C54—C39119.89 (17)
C16—C17—C37120.28 (16)C53—C54—C55120.12 (17)
C37—C17—C18108.40 (16)C55—C54—C39107.78 (16)
C4—C18—C17120.35 (16)C41—C55—C54108.12 (15)
C4—C18—C19120.29 (15)C56—C55—C41119.80 (17)
C17—C18—C19107.50 (15)C56—C55—C54119.95 (17)
C20—C19—C18119.76 (15)C55—C56—C57120.10 (16)
C20—C19—C38120.54 (16)C55—C56—C60119.89 (17)
C38—C19—C18107.37 (15)C60—C56—C57108.01 (15)
C19—C20—C6124.91 (15)C43—C57—C56119.95 (16)
C19—C20—C21119.34 (15)C43—C57—C58120.14 (17)
C21—C20—C6109.86 (14)C58—C57—C56107.90 (15)
C20—C21—C22108.23 (14)C46—C58—C57119.88 (16)
C40—C21—C20121.14 (16)C46—C58—C59119.89 (16)
C40—C21—C22119.97 (16)C57—C58—C59108.20 (16)
C7—C22—C21108.68 (14)C49—C59—C58120.12 (16)
C23—C22—C7121.16 (16)C49—C59—C60120.24 (16)
C23—C22—C21120.09 (16)C60—C59—C58107.68 (15)
C22—C23—C24119.27 (16)C52—C60—C56119.86 (16)
C22—C23—C42119.89 (16)C52—C60—C59120.12 (16)
C24—C23—C42108.42 (15)C59—C60—C56108.21 (16)
C23—C24—C44108.08 (16)O2—C61—C5108.91 (13)
C25—C24—C23119.34 (16)O2—C61—C62113.15 (13)
C25—C24—C44120.00 (17)C62—C61—C5111.24 (13)
C24—C25—C8120.57 (16)C63—C62—C61122.28 (15)
C24—C25—C26119.93 (16)C63—C62—C67120.30 (16)
C26—C25—C8108.33 (16)C67—C62—C61117.38 (15)
C25—C26—C10108.14 (15)C62—C63—C64118.82 (16)
C27—C26—C10120.50 (17)C65—C64—C63121.26 (16)
C27—C26—C25119.82 (17)C64—C65—C66119.73 (16)
C26—C27—C28119.81 (17)C67—C66—C65119.81 (16)
C26—C27—C45120.27 (17)C62—C67—C68118.05 (15)
C45—C27—C28108.14 (16)C66—C67—C62120.06 (16)
C29—C28—C27119.96 (16)C66—C67—C68121.88 (15)
C29—C28—C47120.17 (17)O1—C68—C6108.98 (13)
C47—C28—C27108.01 (16)O1—C68—C67114.01 (13)
C28—C29—C11119.93 (17)C67—C68—C6111.14 (13)
C28—C29—C30119.82 (17)O1—C69—C70119.87 (16)
C30—C29—C11108.12 (16)O1—C69—C74119.06 (15)
C29—C30—C13107.99 (16)C70—C69—C74121.06 (16)
C31—C30—C13119.98 (17)C69—C70—C71118.55 (16)
C31—C30—C29120.09 (17)C72—C71—C70120.64 (17)
C30—C31—C32119.90 (16)C71—C72—C73120.37 (17)
C30—C31—C48119.80 (17)C74—C73—C72119.04 (18)
C48—C31—C32108.16 (16)O2—C74—C69118.98 (16)
C31—C32—C50107.92 (15)O2—C74—C73120.69 (16)
C33—C32—C31119.82 (17)C73—C74—C69120.32 (17)
C33—C32—C50119.87 (17)S1i—S1—C7565.96 (19)
C14—C33—C34108.08 (16)S1—C75—S1ii146.5 (3)
C32—C33—C14119.97 (17)S1ii—C75—S1iii48.1 (4)
C32—C33—C34119.91 (17)S1—C75—S1iii146.5 (3)
C33—C34—C16107.67 (17)S1—C75—S1i48.1 (4)
C35—C34—C16119.80 (17)S1i—C75—S1iii146.5 (3)
C35—C34—C33120.32 (16)S1ii—C75—S1i146.5 (3)
C34—C35—C36120.22 (16)
O1—C69—C70—C71179.91 (15)C28—C29—C30—C13142.22 (16)
O1—C69—C74—O21.1 (2)C28—C29—C30—C310.5 (3)
O1—C69—C74—C73179.79 (16)C28—C47—C48—C310.1 (2)
O2—C61—C62—C63104.02 (18)C28—C47—C48—C49138.10 (17)
O2—C61—C62—C6773.64 (18)C29—C11—C12—C2141.49 (16)
C1—C2—C3—C40.39 (19)C29—C11—C12—C130.37 (19)
C1—C2—C3—C15145.85 (16)C29—C28—C47—C46142.88 (16)
C1—C2—C12—C112.7 (3)C29—C28—C47—C480.2 (3)
C1—C2—C12—C13140.25 (17)C29—C30—C31—C32138.21 (17)
C1—C5—C6—C70.10 (19)C29—C30—C31—C480.2 (3)
C1—C5—C6—C20113.68 (15)C30—C13—C14—C15138.15 (17)
C1—C5—C6—C68124.89 (15)C30—C13—C14—C330.5 (2)
C1—C5—C61—O248.00 (17)C30—C31—C32—C330.2 (3)
C1—C5—C61—C62173.37 (14)C30—C31—C32—C50142.23 (16)
C1—C9—C10—C111.0 (3)C30—C31—C48—C470.1 (2)
C1—C9—C10—C26142.38 (16)C30—C31—C48—C49142.52 (16)
C2—C1—C5—C417.70 (16)C31—C32—C33—C140.1 (3)
C2—C1—C5—C6139.10 (14)C31—C32—C33—C34138.06 (17)
C2—C1—C5—C6193.91 (16)C31—C32—C50—C490.34 (19)
C2—C1—C9—C8136.12 (17)C31—C32—C50—C51142.21 (16)
C2—C1—C9—C101.4 (2)C31—C48—C49—C500.31 (18)
C2—C3—C4—C512.28 (18)C31—C48—C49—C59142.38 (16)
C2—C3—C4—C18142.00 (16)C32—C31—C48—C47142.27 (16)
C2—C3—C15—C141.3 (2)C32—C31—C48—C490.10 (19)
C2—C3—C15—C16138.43 (17)C32—C33—C34—C16142.82 (16)
C2—C12—C13—C140.9 (3)C32—C33—C34—C350.6 (3)
C2—C12—C13—C30141.38 (16)C32—C50—C51—C350.0 (2)
C3—C2—C12—C11138.60 (17)C32—C50—C51—C52138.06 (17)
C3—C2—C12—C131.1 (2)C33—C14—C15—C3141.64 (16)
C3—C4—C5—C117.93 (16)C33—C14—C15—C160.20 (19)
C3—C4—C5—C6139.67 (14)C33—C32—C50—C49142.39 (16)
C3—C4—C5—C6196.10 (15)C33—C32—C50—C510.2 (3)
C3—C4—C18—C171.2 (2)C33—C34—C35—C36137.88 (17)
C3—C4—C18—C19137.04 (16)C33—C34—C35—C510.4 (2)
C3—C15—C16—C170.2 (2)C34—C16—C17—C18139.09 (17)
C3—C15—C16—C34141.63 (16)C34—C16—C17—C371.3 (2)
C4—C3—C15—C14139.66 (17)C34—C35—C36—C370.7 (2)
C4—C3—C15—C162.6 (2)C34—C35—C36—C53142.92 (16)
C4—C5—C6—C7113.21 (15)C34—C35—C51—C500.1 (2)
C4—C5—C6—C200.36 (19)C34—C35—C51—C52142.65 (16)
C4—C5—C6—C68121.80 (15)C35—C36—C37—C170.3 (2)
C4—C5—C61—O2155.00 (13)C35—C36—C37—C38138.62 (17)
C4—C5—C61—C6279.63 (16)C35—C36—C53—C520.62 (19)
C4—C18—C19—C200.5 (2)C35—C36—C53—C54142.91 (17)
C4—C18—C19—C38142.91 (16)C35—C51—C52—C530.52 (19)
C5—C1—C2—C311.72 (18)C35—C51—C52—C60142.72 (16)
C5—C1—C2—C12156.93 (15)C36—C35—C51—C50142.72 (16)
C5—C1—C9—C813.4 (3)C36—C35—C51—C520.13 (19)
C5—C1—C9—C10150.92 (16)C36—C37—C38—C19143.83 (16)
C5—C4—C18—C17151.33 (16)C36—C37—C38—C390.2 (2)
C5—C4—C18—C1913.1 (2)C36—C53—C54—C390.0 (3)
C5—C6—C7—C812.8 (2)C36—C53—C54—C55137.75 (17)
C5—C6—C7—C22139.76 (14)C37—C17—C18—C4143.34 (16)
C5—C6—C20—C1912.5 (2)C37—C17—C18—C190.45 (18)
C5—C6—C20—C21140.04 (14)C37—C36—C53—C52141.69 (17)
C5—C6—C68—O180.86 (16)C37—C36—C53—C540.6 (3)
C5—C6—C68—C6745.61 (18)C37—C38—C39—C40138.02 (17)
C5—C61—C62—C63133.00 (16)C37—C38—C39—C540.4 (2)
C5—C61—C62—C6749.3 (2)C38—C19—C20—C6151.10 (16)
C6—C5—C61—O279.98 (16)C38—C19—C20—C210.9 (2)
C6—C5—C61—C6245.40 (18)C38—C39—C40—C210.3 (2)
C6—C7—C8—C913.6 (2)C38—C39—C40—C41142.19 (16)
C6—C7—C8—C25151.41 (16)C38—C39—C54—C530.6 (3)
C6—C7—C22—C2111.84 (18)C38—C39—C54—C55141.84 (16)
C6—C7—C22—C23157.20 (15)C39—C40—C41—C42142.71 (16)
C6—C20—C21—C2212.40 (18)C39—C40—C41—C550.05 (19)
C6—C20—C21—C40156.85 (15)C39—C54—C55—C410.02 (19)
C7—C6—C20—C19134.45 (16)C39—C54—C55—C56142.36 (16)
C7—C6—C20—C2118.10 (16)C40—C21—C22—C7145.34 (15)
C7—C6—C68—O146.87 (17)C40—C21—C22—C230.5 (2)
C7—C6—C68—C67173.34 (13)C40—C39—C54—C53142.38 (17)
C7—C8—C9—C10.1 (2)C40—C39—C54—C550.01 (19)
C7—C8—C9—C10142.38 (16)C40—C41—C42—C230.4 (2)
C7—C8—C25—C241.0 (2)C40—C41—C42—C43138.24 (17)
C7—C8—C25—C26142.66 (16)C40—C41—C55—C540.04 (19)
C7—C22—C23—C242.6 (2)C40—C41—C55—C56142.40 (16)
C7—C22—C23—C42140.30 (17)C41—C42—C43—C44142.36 (16)
C8—C7—C22—C21142.28 (15)C41—C42—C43—C570.5 (2)
C8—C7—C22—C233.1 (2)C41—C55—C56—C570.2 (2)
C8—C9—C10—C11143.24 (16)C41—C55—C56—C60138.00 (17)
C8—C9—C10—C260.17 (18)C42—C23—C24—C25142.32 (16)
C8—C25—C26—C100.21 (19)C42—C23—C24—C440.43 (18)
C8—C25—C26—C27143.67 (16)C42—C41—C55—C54142.60 (16)
C9—C1—C2—C3141.89 (16)C42—C41—C55—C560.2 (2)
C9—C1—C2—C123.3 (2)C42—C43—C44—C240.37 (18)
C9—C1—C5—C4134.07 (17)C42—C43—C44—C45142.17 (16)
C9—C1—C5—C612.7 (2)C42—C43—C57—C560.5 (2)
C9—C1—C5—C61114.31 (18)C42—C43—C57—C58137.69 (17)
C9—C8—C25—C24143.61 (16)C43—C44—C45—C27137.96 (17)
C9—C8—C25—C260.10 (18)C43—C44—C45—C460.1 (2)
C9—C10—C11—C121.6 (3)C43—C57—C58—C460.3 (2)
C9—C10—C11—C29138.57 (17)C43—C57—C58—C59142.84 (16)
C9—C10—C26—C250.24 (19)C44—C24—C25—C8138.90 (17)
C9—C10—C26—C27143.41 (16)C44—C24—C25—C260.7 (2)
C10—C11—C12—C20.2 (3)C44—C43—C57—C56137.88 (17)
C10—C11—C12—C13142.12 (16)C44—C43—C57—C580.3 (2)
C10—C11—C29—C280.8 (3)C44—C45—C46—C47143.14 (16)
C10—C11—C29—C30141.59 (17)C44—C45—C46—C580.1 (2)
C10—C26—C27—C280.2 (2)C45—C27—C28—C29143.43 (16)
C10—C26—C27—C45138.81 (17)C45—C27—C28—C470.55 (19)
C11—C10—C26—C25143.61 (16)C45—C46—C47—C280.40 (19)
C11—C10—C26—C270.4 (2)C45—C46—C47—C48143.13 (16)
C11—C12—C13—C14142.50 (16)C45—C46—C58—C570.2 (2)
C11—C12—C13—C300.24 (19)C45—C46—C58—C59138.44 (17)
C11—C29—C30—C130.21 (19)C46—C47—C48—C31138.01 (17)
C11—C29—C30—C31142.90 (16)C46—C47—C48—C490.0 (2)
C12—C2—C3—C4145.45 (16)C46—C58—C59—C490.6 (2)
C12—C2—C3—C150.0 (2)C46—C58—C59—C60142.16 (16)
C12—C11—C29—C28142.02 (17)C47—C28—C29—C11138.52 (17)
C12—C11—C29—C300.36 (19)C47—C28—C29—C300.5 (2)
C12—C13—C14—C150.4 (2)C47—C46—C58—C57138.78 (17)
C12—C13—C14—C33138.16 (17)C47—C46—C58—C590.5 (2)
C12—C13—C30—C290.02 (19)C47—C48—C49—C50142.08 (16)
C12—C13—C30—C31142.73 (16)C47—C48—C49—C590.0 (2)
C13—C14—C15—C31.5 (2)C48—C31—C32—C33142.21 (16)
C13—C14—C15—C16142.98 (16)C48—C31—C32—C500.15 (19)
C13—C14—C33—C320.2 (3)C48—C49—C50—C320.40 (18)
C13—C14—C33—C34142.75 (16)C48—C49—C50—C51142.24 (16)
C13—C30—C31—C320.1 (2)C48—C49—C59—C580.3 (2)
C13—C30—C31—C48138.13 (17)C48—C49—C59—C60137.81 (17)
C14—C13—C30—C29142.36 (16)C49—C50—C51—C35138.21 (17)
C14—C13—C30—C310.4 (3)C49—C50—C51—C520.1 (2)
C14—C15—C16—C17141.76 (16)C49—C59—C60—C520.3 (2)
C14—C15—C16—C340.04 (18)C49—C59—C60—C56143.10 (16)
C14—C33—C34—C160.27 (19)C50—C32—C33—C14137.67 (17)
C14—C33—C34—C35141.97 (16)C50—C32—C33—C340.5 (3)
C15—C3—C4—C5157.35 (15)C50—C49—C59—C58137.96 (17)
C15—C3—C4—C183.1 (2)C50—C49—C59—C600.2 (2)
C15—C14—C33—C32142.82 (16)C50—C51—C52—C53143.05 (16)
C15—C14—C33—C340.29 (19)C50—C51—C52—C600.2 (2)
C15—C16—C17—C181.7 (2)C51—C35—C36—C37141.93 (17)
C15—C16—C17—C37138.69 (17)C51—C35—C36—C530.30 (19)
C15—C16—C34—C330.14 (19)C51—C52—C53—C360.70 (19)
C15—C16—C34—C35142.33 (16)C51—C52—C53—C54143.13 (17)
C16—C17—C18—C41.2 (2)C51—C52—C60—C56138.83 (17)
C16—C17—C18—C19144.08 (16)C51—C52—C60—C590.3 (2)
C16—C17—C37—C360.7 (2)C52—C53—C54—C39137.88 (17)
C16—C17—C37—C38143.93 (16)C52—C53—C54—C550.1 (3)
C16—C34—C35—C360.1 (2)C53—C36—C37—C17138.16 (17)
C16—C34—C35—C51138.11 (17)C53—C36—C37—C380.7 (3)
C17—C16—C34—C33141.61 (17)C53—C52—C60—C560.1 (3)
C17—C16—C34—C350.9 (3)C53—C52—C60—C59138.49 (17)
C17—C18—C19—C20142.40 (16)C53—C54—C55—C41142.31 (16)
C17—C18—C19—C380.01 (18)C53—C54—C55—C560.1 (3)
C17—C37—C38—C190.74 (19)C54—C39—C40—C21141.86 (16)
C17—C37—C38—C39142.88 (16)C54—C39—C40—C410.04 (19)
C18—C4—C5—C1134.54 (16)C54—C55—C56—C57138.24 (17)
C18—C4—C5—C612.8 (2)C54—C55—C56—C600.0 (2)
C18—C4—C5—C61111.43 (17)C55—C41—C42—C23137.69 (17)
C18—C17—C37—C36143.93 (16)C55—C41—C42—C430.2 (2)
C18—C17—C37—C380.74 (19)C55—C56—C57—C430.1 (2)
C18—C19—C20—C613.7 (2)C55—C56—C57—C58142.56 (16)
C18—C19—C20—C21136.52 (16)C55—C56—C60—C520.0 (3)
C18—C19—C38—C370.46 (18)C55—C56—C60—C59142.90 (16)
C18—C19—C38—C39143.02 (16)C56—C57—C58—C46142.31 (16)
C19—C20—C21—C22141.89 (16)C56—C57—C58—C590.26 (19)
C19—C20—C21—C402.6 (2)C57—C43—C44—C24142.35 (16)
C19—C38—C39—C401.3 (2)C57—C43—C44—C450.2 (2)
C19—C38—C39—C54138.89 (17)C57—C56—C60—C52142.71 (16)
C20—C6—C7—C8134.74 (16)C57—C56—C60—C590.23 (19)
C20—C6—C7—C2217.85 (16)C57—C58—C59—C49143.16 (16)
C20—C6—C68—O1153.44 (13)C57—C58—C59—C600.40 (19)
C20—C6—C68—C6780.09 (16)C58—C46—C47—C28142.95 (16)
C20—C19—C38—C37142.50 (16)C58—C46—C47—C480.2 (2)
C20—C19—C38—C391.0 (2)C58—C59—C60—C52142.44 (16)
C20—C21—C22—C70.40 (18)C58—C59—C60—C560.39 (19)
C20—C21—C22—C23145.40 (15)C59—C49—C50—C32142.55 (16)
C20—C21—C40—C392.2 (2)C59—C49—C50—C510.1 (2)
C20—C21—C40—C41139.68 (17)C60—C52—C53—C36142.34 (17)
C21—C22—C23—C24138.94 (17)C60—C52—C53—C540.1 (3)
C21—C22—C23—C421.2 (2)C60—C56—C57—C43142.69 (16)
C21—C40—C41—C421.1 (2)C60—C56—C57—C580.02 (19)
C21—C40—C41—C55141.54 (16)C61—O2—C74—C6976.4 (2)
C22—C7—C8—C9136.62 (16)C61—O2—C74—C73104.46 (19)
C22—C7—C8—C251.2 (2)C61—C5—C6—C7125.72 (15)
C22—C21—C40—C39138.17 (16)C61—C5—C6—C20120.71 (15)
C22—C21—C40—C410.7 (2)C61—C5—C6—C680.72 (19)
C22—C23—C24—C250.3 (2)C61—C62—C63—C64178.36 (15)
C22—C23—C24—C44141.64 (16)C61—C62—C67—C66177.08 (15)
C22—C23—C42—C410.8 (2)C61—C62—C67—C681.7 (2)
C22—C23—C42—C43141.59 (16)C62—C63—C64—C651.4 (3)
C23—C24—C25—C81.5 (2)C62—C67—C68—O176.77 (18)
C23—C24—C25—C26138.04 (17)C62—C67—C68—C646.9 (2)
C23—C24—C44—C430.49 (18)C63—C62—C67—C660.6 (2)
C23—C24—C44—C45142.21 (16)C63—C62—C67—C68179.43 (15)
C23—C42—C43—C440.10 (18)C63—C64—C65—C660.6 (3)
C23—C42—C43—C57141.97 (16)C64—C65—C66—C670.8 (3)
C24—C23—C42—C41142.60 (16)C65—C66—C67—C621.4 (2)
C24—C23—C42—C430.21 (18)C65—C66—C67—C68179.82 (15)
C24—C25—C26—C10143.77 (16)C66—C67—C68—O1102.01 (18)
C24—C25—C26—C270.3 (2)C66—C67—C68—C6134.35 (16)
C24—C44—C45—C270.2 (2)C67—C62—C63—C640.8 (2)
C24—C44—C45—C46138.01 (17)C68—O1—C69—C70106.84 (17)
C25—C8—C9—C1142.51 (16)C68—O1—C69—C7474.07 (19)
C25—C8—C9—C100.04 (18)C68—C6—C7—C8114.12 (17)
C25—C24—C44—C43142.09 (16)C68—C6—C7—C2293.29 (16)
C25—C24—C44—C450.6 (2)C68—C6—C20—C19112.37 (17)
C25—C26—C27—C28138.73 (17)C68—C6—C20—C2195.09 (15)
C25—C26—C27—C450.1 (2)C69—O1—C68—C6123.71 (15)
C26—C10—C11—C12137.90 (17)C69—O1—C68—C671.1 (2)
C26—C10—C11—C290.9 (2)C69—C70—C71—C720.2 (3)
C26—C27—C28—C290.4 (3)C70—C69—C74—O2177.97 (15)
C26—C27—C28—C47142.49 (16)C70—C69—C74—C731.1 (3)
C26—C27—C45—C440.2 (3)C70—C71—C72—C730.2 (3)
C26—C27—C45—C46142.04 (16)C71—C72—C73—C740.0 (3)
C27—C28—C29—C110.1 (3)C72—C73—C74—O2178.38 (16)
C27—C28—C29—C30137.92 (17)C72—C73—C74—C690.7 (3)
C27—C28—C47—C460.09 (19)C74—O2—C61—C5123.13 (15)
C27—C28—C47—C48142.60 (16)C74—O2—C61—C621.1 (2)
C27—C45—C46—C470.74 (19)C74—C69—C70—C710.8 (2)
C27—C45—C46—C58142.53 (16)S1i—S1—C75—S1ii132.40 (4)
C28—C27—C45—C44143.06 (16)S1i—S1—C75—S1iii132.40 (4)
C28—C27—C45—C460.80 (19)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) y+1/2, x, z+1/2; (iii) y, x+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC74H10O2·0.1(CS2)
Mr938.68
Crystal system, space groupTetragonal, P42/n
Temperature (K)100
a, c (Å)22.66570 (13), 14.24938 (11)
V3)7320.40 (10)
Z8
Radiation typeCu Kα
µ (mm1)0.91
Crystal size (mm)0.18 × 0.15 × 0.08
Data collection
DiffractometerAgilent SuperNova (Dual, Cu at zero, Atlas)
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2012)
Tmin, Tmax0.911, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
35247, 7171, 6473
Rint0.021
(sin θ/λ)max1)0.619
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.120, 1.04
No. of reflections7171
No. of parameters696
No. of restraints7
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.02, 0.74

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Olex2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008), publCIF (Westrip, 2010).

 

Acknowledgements

This work was supported by OTKA, the Hungarian Research Fund (grant No. NK105691). GB and ÉK acknowledge the support of the Bolyai János Scholarship of the Hungarian Academy of Sciences.

References

First citationAgilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
First citationBortel, G., Oszlányi, G., Faigel, G., Tegze, M., Pusztai, T. & Pekker, S. (1995). Mater. Sci. Forum, 228–231, 879–884.  CrossRef Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationRigaudy, J., Breliere, C. & Scribe, P. (1978). Tetrahedron Lett. 7, 687–690.  CrossRef Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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