Rubrene endoperoxide acetone monosolvate

Shinashi, K.; Uchida, A.

doi:10.1107/S1600536812008835

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o995-o996

doi:10.1107/S1600536812008835

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Rubrene endoperoxide acetone monosolvate

Kiyoaki Shinashi ^a and Akira Uchida ^b ^*

^aDepartment of Law, Faculty of Law, Chuogakuin University, Kujike 451, Abiko, Chiba 270-1196, Japan, and ^bDepartment of Biomolecular Science, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan
^*Correspondence e-mail: auchida@biomol.sci.toho-u.ac.jp

(Received 18 February 2012; accepted 28 February 2012; online 10 March 2012)

The title acetone solvate, C₄₂H₂₈O₂·C₃H₆O [systematic name: 1,3,10,12-tetraphenyl-19,20-dioxapentacyclo[10.6.2.0^2,11.0^4,9.0^13,18]icosa-2(11),3,5,7,9,13,15,17-octaene acetone monosolvate], is a photooxygenation product of rubrene (systematic name: 5,6,11,12-tetraphenyltetracene). The molecule bends at the bridgehead atoms, which are linked by the O—O transannular bond, with a dihedral angle of 49.21 (6)° between the benzene ring and the naphthalene ring system of the tetracene unit. In the crystal, the rubrene molecules are linked by C—H⋯O hydrogen bonds into a column along the c axis. The acetone solvent molecules form a dimer around a crystallographic inversion centre through a carbonyl–carbonyl dipolar interaction. A C—H⋯O hydrogen bond between the rubrene and acetone molecules is also observed.

Related literature

For related structures, see: Brown & Ehrenberg (1984 ); Izuoka et al. (1997 ); Schuster et al. (2002 ); Usman et al. (2003 ); Wang (2008 ). For background to photooxygenation of polycyclic aromatic hydrocarbons, see: Sakai et al. (1995 ).

Experimental

Crystal data

C₄₂H₂₈O₂·C₃H₆O
M_r = 622.72
Monoclinic, P 2₁ /c
a = 11.1592 (6) Å
b = 21.2248 (11) Å
c = 13.6121 (7) Å
β = 103.113 (1)°
V = 3140.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 90 K
0.15 × 0.07 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.988, T_max = 0.996
20867 measured reflections
7642 independent reflections
5257 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.119
S = 1.03
7642 reflections
435 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯O3ⁱ	0.95	2.53	3.437 (2)	159
C35—H35⋯O1ⁱⁱ	0.95	2.59	3.408 (2)	144
Symmetry codes: (i) $[x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812008835/is5077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008835/is5077Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008835/is5077Isup3.mol

Supporting information file. DOI: 10.1107/S1600536812008835/is5077Isup4.cml

checkCIF report

Comment top

Polycyclic aromatic hydrocarbons (PAHs) in solution are known to react with molecular oxygen to form endoperoxides when PAHs are irradiated by light with their absorption wavelength. The photooxygenation of PAHs occur due to 1,4-cycloaddition of singlet oxygen to the ground state of a PAH molecule (Sakai et al., 1995). We present here the crystal structure of the title compound.

The molecule bends at the bridgehead atoms, C9 and C10, with a dihedral angle of 49.21 (6)° between the benzene C1–C4/C14/C13 ring and the naphthalene C5–C8/C17/C11/C15/C16/C12/C18 ring system (Figure 1). The adjacent phenyl groups [C19—C24 (centroid Cg1), C25—C30 (centroid Cg2), C31—C36 (centroid Cg3), C37—C42 (centroid Cg4)] on either side of the molecule adopt a splayed face-to-face geometry with Cg1···Cg3 distance of 3.455 (1) Å and Cg2···Cg4 distance of 3.491 (1) Å (Figure 2). The molecules related by glide plane are linked by C—H···O hydrogen bonds along the c axis.

Related literature top

For related structures, see: Brown & Ehrenberg (1984); Izuoka et al. (1997); Schuster et al. (2002); Usman et al. (2003); Wang (2008). For background to photooxygenation of polycyclic aromatic hydrocarbons, see: Sakai et al. (1995).

Experimental top

Rubrene was purchased from Sigma-Aldrich. An acetone solution of the compound was exposed to sunlight until the solution became colourless. Crystals of the title compound were obtained from the solution placed in the dark.

Structure description top

For related structures, see: Brown & Ehrenberg (1984); Izuoka et al. (1997); Schuster et al. (2002); Usman et al. (2003); Wang (2008). For background to photooxygenation of polycyclic aromatic hydrocarbons, see: Sakai et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. The dashed lines indicate C—H···O intermolecular interactions.

1,3,10,12-tetraphenyl-19,20- dioxapentacyclo[10.6.2.0^2,11.0^4,9.0^13,18]icosa- 2(11),3,5,7,9,13,15,17-octaene acetone monosolvate top

Crystal data top

C₄₂H₂₈O₂·C₃H₆O	F(000) = 1312
M_r = 622.72	D_x = 1.317 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3033 reflections
a = 11.1592 (6) Å	θ = 2.3–26.7°
b = 21.2248 (11) Å	µ = 0.08 mm⁻¹
c = 13.6121 (7) Å	T = 90 K
β = 103.113 (1)°	Plate, colourless
V = 3140.0 (3) Å³	0.15 × 0.07 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	7642 independent reflections
Radiation source: fine-focus sealed tube	5257 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 8.366 pixels mm^-1	θ_max = 28.1°, θ_min = 1.8°
φ and ω scans	h = −14→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −28→23
T_min = 0.988, T_max = 0.996	l = −17→18
20867 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0487P)² + 0.4529P] where P = (F_o² + 2F_c²)/3
7642 reflections	(Δ/σ)_max = 0.001
435 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₄₂H₂₈O₂·C₃H₆O	V = 3140.0 (3) Å³
M_r = 622.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.1592 (6) Å	µ = 0.08 mm⁻¹
b = 21.2248 (11) Å	T = 90 K
c = 13.6121 (7) Å	0.15 × 0.07 × 0.05 mm
β = 103.113 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	7642 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5257 reflections with I > 2σ(I)
T_min = 0.988, T_max = 0.996	R_int = 0.046
20867 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	Δρ_max = 0.39 e Å⁻³
7642 reflections	Δρ_min = −0.29 e Å⁻³
435 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.18118 (10)	0.61054 (5)	0.17937 (8)	0.0153 (2)
O2	0.08624 (10)	0.61524 (5)	0.23817 (8)	0.0159 (2)
O3	0.56171 (15)	0.92967 (6)	0.04751 (10)	0.0425 (4)
C1	0.00522 (15)	0.57338 (7)	−0.06128 (11)	0.0157 (3)
H1	0.0677	0.5707	−0.0983	0.019*
C2	−0.10563 (15)	0.54225 (7)	−0.09559 (12)	0.0172 (3)
H2	−0.1206	0.5200	−0.1578	0.021*
C3	−0.19435 (15)	0.54349 (7)	−0.03941 (12)	0.0179 (3)
H3	−0.2699	0.5219	−0.0630	0.021*
C4	−0.17376 (15)	0.57614 (7)	0.05126 (12)	0.0161 (3)
H4	−0.2333	0.5752	0.0912	0.019*
C5	0.00268 (15)	0.88782 (7)	0.19322 (12)	0.0174 (3)
H5	−0.0624	0.8908	0.2274	0.021*
C6	0.06089 (16)	0.94148 (7)	0.17353 (12)	0.0201 (4)
H6	0.0358	0.9812	0.1939	0.024*
C7	0.15725 (16)	0.93803 (7)	0.12347 (12)	0.0219 (4)
H7	0.1977	0.9754	0.1103	0.026*
C8	0.19347 (15)	0.88095 (7)	0.09338 (12)	0.0187 (3)
H8	0.2592	0.8792	0.0597	0.022*
C9	0.14375 (14)	0.64156 (7)	0.07997 (11)	0.0139 (3)
C10	−0.02556 (14)	0.64712 (7)	0.18133 (11)	0.0132 (3)
C11	0.17197 (14)	0.76393 (7)	0.08028 (11)	0.0141 (3)
C12	−0.02111 (14)	0.77070 (7)	0.18730 (11)	0.0135 (3)
C13	0.02509 (14)	0.60853 (7)	0.02736 (11)	0.0128 (3)
C14	−0.06515 (14)	0.61037 (6)	0.08337 (11)	0.0135 (3)
C15	0.11456 (14)	0.70993 (7)	0.10355 (11)	0.0131 (3)
C16	0.01819 (14)	0.71332 (7)	0.15861 (11)	0.0131 (3)
C17	0.13408 (14)	0.82406 (7)	0.11186 (11)	0.0146 (3)
C18	0.03779 (14)	0.82748 (7)	0.16346 (11)	0.0145 (3)
C19	0.25208 (14)	0.62739 (7)	0.03296 (12)	0.0146 (3)
C20	0.35961 (15)	0.60032 (7)	0.08973 (13)	0.0179 (3)
H20	0.3679	0.5935	0.1599	0.021*
C21	0.45484 (16)	0.58325 (7)	0.04452 (14)	0.0230 (4)
H21	0.5275	0.5646	0.0839	0.028*
C22	0.44413 (16)	0.59327 (8)	−0.05728 (14)	0.0254 (4)
H22	0.5084	0.5807	−0.0884	0.030*
C23	0.33927 (16)	0.62178 (8)	−0.11395 (13)	0.0226 (4)
H23	0.3327	0.6299	−0.1836	0.027*
C24	0.24402 (15)	0.63844 (7)	−0.06923 (12)	0.0176 (3)
H24	0.1722	0.6577	−0.1088	0.021*
C25	−0.11396 (15)	0.64040 (7)	0.25125 (11)	0.0150 (3)
C26	−0.23815 (15)	0.65513 (7)	0.21634 (12)	0.0163 (3)
H26	−0.2665	0.6708	0.1497	0.020*
C27	−0.32065 (15)	0.64729 (7)	0.27750 (12)	0.0204 (4)
H27	−0.4051	0.6572	0.2525	0.024*
C28	−0.28005 (16)	0.62495 (7)	0.37559 (13)	0.0220 (4)
H28	−0.3364	0.6196	0.4178	0.026*
C29	−0.15715 (16)	0.61064 (7)	0.41095 (13)	0.0208 (4)
H29	−0.1289	0.5957	0.4780	0.025*
C30	−0.07414 (15)	0.61793 (7)	0.34927 (12)	0.0173 (3)
H30	0.0101	0.6075	0.3742	0.021*
C31	0.27087 (14)	0.76655 (7)	0.02205 (12)	0.0147 (3)
C32	0.39281 (14)	0.75275 (7)	0.06683 (12)	0.0167 (3)
H32	0.4146	0.7399	0.1354	0.020*
C33	0.48295 (15)	0.75768 (7)	0.01173 (13)	0.0208 (4)
H33	0.5658	0.7473	0.0424	0.025*
C34	0.45275 (16)	0.77769 (7)	−0.08750 (13)	0.0218 (4)
H34	0.5146	0.7806	−0.1251	0.026*
C35	0.33226 (16)	0.79350 (7)	−0.13213 (13)	0.0207 (4)
H35	0.3116	0.8081	−0.1999	0.025*
C36	0.24205 (15)	0.78793 (7)	−0.07754 (12)	0.0174 (3)
H36	0.1595	0.7988	−0.1083	0.021*
C37	−0.12262 (14)	0.78122 (7)	0.24124 (11)	0.0144 (3)
C38	−0.23453 (15)	0.80595 (7)	0.18777 (12)	0.0178 (3)
H38	−0.2470	0.8129	0.1172	0.021*
C39	−0.32743 (15)	0.82053 (7)	0.23616 (13)	0.0217 (4)
H39	−0.4033	0.8370	0.1988	0.026*
C40	−0.30963 (16)	0.81102 (7)	0.33911 (14)	0.0224 (4)
H40	−0.3733	0.8210	0.3725	0.027*
C41	−0.19894 (16)	0.78702 (7)	0.39326 (13)	0.0205 (4)
H41	−0.1871	0.7802	0.4638	0.025*
C42	−0.10512 (15)	0.77285 (7)	0.34508 (12)	0.0159 (3)
H42	−0.0287	0.7574	0.3831	0.019*
C43	0.59016 (18)	0.97168 (8)	0.10896 (13)	0.0279 (4)
C44	0.5198 (2)	0.98239 (9)	0.18860 (15)	0.0382 (5)
H44A	0.4545	0.9507	0.1822	0.057*
H44B	0.4831	1.0246	0.1806	0.057*
H44C	0.5755	0.9789	0.2553	0.057*
C45	0.6960 (2)	1.01456 (11)	0.10861 (17)	0.0483 (6)
H45A	0.7428	0.9987	0.0610	0.072*
H45B	0.7495	1.0162	0.1764	0.072*
H45C	0.6651	1.0569	0.0882	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0139 (6)	0.0193 (6)	0.0138 (5)	0.0032 (4)	0.0054 (5)	0.0022 (4)
O2	0.0144 (6)	0.0206 (6)	0.0140 (5)	0.0026 (4)	0.0060 (5)	0.0033 (4)
O3	0.0684 (11)	0.0293 (7)	0.0296 (8)	0.0031 (7)	0.0111 (8)	−0.0067 (6)
C1	0.0177 (8)	0.0144 (7)	0.0154 (8)	0.0020 (6)	0.0049 (7)	0.0025 (6)
C2	0.0223 (9)	0.0141 (7)	0.0136 (8)	0.0013 (6)	0.0004 (7)	−0.0003 (6)
C3	0.0161 (8)	0.0135 (7)	0.0223 (8)	−0.0017 (6)	0.0006 (7)	0.0006 (6)
C4	0.0152 (8)	0.0138 (7)	0.0194 (8)	0.0001 (6)	0.0042 (7)	0.0005 (6)
C5	0.0206 (8)	0.0174 (8)	0.0141 (8)	0.0005 (6)	0.0039 (7)	−0.0003 (6)
C6	0.0268 (9)	0.0138 (8)	0.0197 (8)	−0.0006 (7)	0.0054 (7)	−0.0019 (6)
C7	0.0292 (10)	0.0134 (8)	0.0248 (9)	−0.0050 (7)	0.0093 (8)	0.0004 (6)
C8	0.0217 (9)	0.0179 (8)	0.0184 (8)	−0.0028 (7)	0.0083 (7)	0.0009 (6)
C9	0.0150 (8)	0.0149 (7)	0.0120 (7)	0.0001 (6)	0.0031 (6)	0.0007 (6)
C10	0.0120 (7)	0.0120 (7)	0.0150 (8)	0.0007 (6)	0.0021 (6)	0.0009 (6)
C11	0.0130 (8)	0.0167 (7)	0.0120 (7)	0.0001 (6)	0.0014 (6)	0.0006 (6)
C12	0.0137 (8)	0.0154 (7)	0.0103 (7)	0.0004 (6)	0.0004 (6)	0.0001 (6)
C13	0.0135 (8)	0.0100 (7)	0.0139 (8)	0.0018 (6)	0.0009 (6)	0.0029 (6)
C14	0.0164 (8)	0.0088 (7)	0.0149 (8)	0.0017 (6)	0.0029 (6)	0.0014 (6)
C15	0.0130 (7)	0.0140 (7)	0.0111 (7)	0.0006 (6)	0.0004 (6)	−0.0002 (6)
C16	0.0130 (8)	0.0153 (7)	0.0106 (7)	−0.0013 (6)	0.0017 (6)	0.0013 (6)
C17	0.0166 (8)	0.0151 (7)	0.0115 (7)	−0.0011 (6)	0.0022 (6)	−0.0003 (6)
C18	0.0163 (8)	0.0151 (7)	0.0112 (7)	−0.0003 (6)	0.0015 (6)	−0.0005 (6)
C19	0.0154 (8)	0.0103 (7)	0.0184 (8)	−0.0014 (6)	0.0041 (7)	−0.0033 (6)
C20	0.0169 (8)	0.0150 (8)	0.0220 (9)	−0.0016 (6)	0.0049 (7)	−0.0002 (6)
C21	0.0176 (9)	0.0169 (8)	0.0356 (10)	0.0006 (7)	0.0085 (8)	0.0003 (7)
C22	0.0228 (9)	0.0191 (8)	0.0389 (11)	−0.0024 (7)	0.0167 (9)	−0.0066 (7)
C23	0.0259 (10)	0.0213 (8)	0.0235 (9)	−0.0069 (7)	0.0117 (8)	−0.0048 (7)
C24	0.0177 (8)	0.0163 (8)	0.0189 (8)	−0.0026 (6)	0.0044 (7)	−0.0037 (6)
C25	0.0191 (8)	0.0100 (7)	0.0172 (8)	−0.0025 (6)	0.0067 (7)	−0.0024 (6)
C26	0.0190 (8)	0.0130 (7)	0.0176 (8)	−0.0034 (6)	0.0054 (7)	−0.0013 (6)
C27	0.0180 (9)	0.0184 (8)	0.0261 (9)	−0.0034 (7)	0.0076 (7)	−0.0050 (7)
C28	0.0276 (10)	0.0185 (8)	0.0244 (9)	−0.0049 (7)	0.0155 (8)	−0.0045 (7)
C29	0.0302 (10)	0.0152 (8)	0.0191 (9)	−0.0031 (7)	0.0101 (8)	0.0001 (6)
C30	0.0200 (9)	0.0140 (7)	0.0186 (8)	−0.0008 (6)	0.0058 (7)	0.0000 (6)
C31	0.0163 (8)	0.0107 (7)	0.0178 (8)	−0.0022 (6)	0.0051 (7)	−0.0012 (6)
C32	0.0172 (8)	0.0164 (8)	0.0157 (8)	−0.0027 (6)	0.0024 (7)	−0.0003 (6)
C33	0.0139 (8)	0.0184 (8)	0.0297 (10)	−0.0003 (6)	0.0041 (7)	0.0003 (7)
C34	0.0225 (9)	0.0187 (8)	0.0286 (10)	0.0000 (7)	0.0150 (8)	0.0030 (7)
C35	0.0262 (9)	0.0192 (8)	0.0189 (8)	0.0023 (7)	0.0095 (7)	0.0042 (6)
C36	0.0168 (8)	0.0165 (8)	0.0185 (8)	0.0008 (6)	0.0029 (7)	0.0020 (6)
C37	0.0167 (8)	0.0100 (7)	0.0175 (8)	−0.0012 (6)	0.0057 (7)	−0.0020 (6)
C38	0.0176 (8)	0.0159 (8)	0.0191 (8)	−0.0018 (6)	0.0026 (7)	0.0012 (6)
C39	0.0154 (8)	0.0149 (8)	0.0353 (10)	0.0012 (6)	0.0067 (8)	−0.0004 (7)
C40	0.0219 (9)	0.0171 (8)	0.0327 (10)	−0.0037 (7)	0.0155 (8)	−0.0068 (7)
C41	0.0271 (9)	0.0167 (8)	0.0200 (9)	−0.0066 (7)	0.0102 (7)	−0.0040 (6)
C42	0.0177 (8)	0.0124 (7)	0.0175 (8)	−0.0029 (6)	0.0037 (7)	−0.0023 (6)
C43	0.0367 (11)	0.0251 (9)	0.0203 (9)	0.0068 (8)	0.0032 (8)	0.0025 (7)
C44	0.0422 (13)	0.0383 (11)	0.0361 (11)	0.0029 (9)	0.0129 (10)	−0.0065 (9)
C45	0.0463 (14)	0.0614 (15)	0.0359 (12)	−0.0137 (11)	0.0068 (11)	0.0054 (11)

Geometric parameters (Å, º) top

O1—O2	1.4689 (14)	C23—C24	1.385 (2)
O1—C9	1.4772 (18)	C23—H23	0.9500
O2—C10	1.4749 (18)	C24—H24	0.9500
O3—C43	1.214 (2)	C25—C30	1.391 (2)
C1—C2	1.387 (2)	C25—C26	1.395 (2)
C1—C13	1.393 (2)	C26—C27	1.384 (2)
C1—H1	0.9500	C26—H26	0.9500
C2—C3	1.382 (2)	C27—C28	1.392 (2)
C2—H2	0.9500	C27—H27	0.9500
C3—C4	1.388 (2)	C28—C29	1.380 (2)
C3—H3	0.9500	C28—H28	0.9500
C4—C14	1.396 (2)	C29—C30	1.393 (2)
C4—H4	0.9500	C29—H29	0.9500
C5—C6	1.367 (2)	C30—H30	0.9500
C5—C18	1.425 (2)	C31—C32	1.390 (2)
C5—H5	0.9500	C31—C36	1.396 (2)
C6—C7	1.399 (2)	C32—C33	1.388 (2)
C6—H6	0.9500	C32—H32	0.9500
C7—C8	1.369 (2)	C33—C34	1.383 (2)
C7—H7	0.9500	C33—H33	0.9500
C8—C17	1.427 (2)	C34—C35	1.385 (2)
C8—H8	0.9500	C34—H34	0.9500
C9—C19	1.521 (2)	C35—C36	1.385 (2)
C9—C13	1.526 (2)	C35—H35	0.9500
C9—C15	1.537 (2)	C36—H36	0.9500
C10—C14	1.521 (2)	C37—C42	1.394 (2)
C10—C25	1.525 (2)	C37—C38	1.397 (2)
C10—C16	1.542 (2)	C38—C39	1.384 (2)
C11—C15	1.384 (2)	C38—H38	0.9500
C11—C17	1.440 (2)	C39—C40	1.385 (2)
C11—C31	1.499 (2)	C39—H39	0.9500
C12—C16	1.380 (2)	C40—C41	1.384 (2)
C12—C18	1.444 (2)	C40—H40	0.9500
C12—C37	1.500 (2)	C41—C42	1.389 (2)
C13—C14	1.395 (2)	C41—H41	0.9500
C15—C16	1.445 (2)	C42—H42	0.9500
C17—C18	1.413 (2)	C43—C45	1.492 (3)
C19—C24	1.393 (2)	C43—C44	1.493 (2)
C19—C20	1.395 (2)	C44—H44A	0.9800
C20—C21	1.391 (2)	C44—H44B	0.9800
C20—H20	0.9500	C44—H44C	0.9800
C21—C22	1.380 (2)	C45—H45A	0.9800
C21—H21	0.9500	C45—H45B	0.9800
C22—C23	1.386 (2)	C45—H45C	0.9800
C22—H22	0.9500

O2—O1—C9	112.32 (10)	C24—C23—H23	119.9
O1—O2—C10	111.97 (9)	C22—C23—H23	119.9
C2—C1—C13	120.10 (14)	C23—C24—C19	120.90 (16)
C2—C1—H1	120.0	C23—C24—H24	119.6
C13—C1—H1	120.0	C19—C24—H24	119.6
C3—C2—C1	120.07 (14)	C30—C25—C26	118.69 (14)
C3—C2—H2	120.0	C30—C25—C10	121.29 (14)
C1—C2—H2	120.0	C26—C25—C10	119.99 (14)
C2—C3—C4	120.44 (15)	C27—C26—C25	120.88 (15)
C2—C3—H3	119.8	C27—C26—H26	119.6
C4—C3—H3	119.8	C25—C26—H26	119.6
C3—C4—C14	119.67 (14)	C26—C27—C28	120.10 (16)
C3—C4—H4	120.2	C26—C27—H27	119.9
C14—C4—H4	120.2	C28—C27—H27	119.9
C6—C5—C18	121.30 (15)	C29—C28—C27	119.40 (15)
C6—C5—H5	119.4	C29—C28—H28	120.3
C18—C5—H5	119.4	C27—C28—H28	120.3
C5—C6—C7	120.24 (14)	C28—C29—C30	120.62 (16)
C5—C6—H6	119.9	C28—C29—H29	119.7
C7—C6—H6	119.9	C30—C29—H29	119.7
C8—C7—C6	120.24 (14)	C25—C30—C29	120.31 (15)
C8—C7—H7	119.9	C25—C30—H30	119.8
C6—C7—H7	119.9	C29—C30—H30	119.8
C7—C8—C17	121.05 (15)	C32—C31—C36	118.76 (14)
C7—C8—H8	119.5	C32—C31—C11	121.69 (14)
C17—C8—H8	119.5	C36—C31—C11	119.38 (14)
O1—C9—C19	102.17 (12)	C33—C32—C31	120.29 (15)
O1—C9—C13	105.08 (11)	C33—C32—H32	119.9
C19—C9—C13	113.57 (12)	C31—C32—H32	119.9
O1—C9—C15	105.00 (11)	C34—C33—C32	120.33 (16)
C19—C9—C15	120.06 (12)	C34—C33—H33	119.8
C13—C9—C15	109.23 (12)	C32—C33—H33	119.8
O2—C10—C14	105.51 (11)	C33—C34—C35	120.00 (15)
O2—C10—C25	102.69 (11)	C33—C34—H34	120.0
C14—C10—C25	113.50 (12)	C35—C34—H34	120.0
O2—C10—C16	104.75 (11)	C36—C35—C34	119.69 (15)
C14—C10—C16	109.49 (12)	C36—C35—H35	120.2
C25—C10—C16	119.31 (12)	C34—C35—H35	120.2
C15—C11—C17	118.87 (13)	C35—C36—C31	120.87 (15)
C15—C11—C31	125.89 (13)	C35—C36—H36	119.6
C17—C11—C31	115.23 (13)	C31—C36—H36	119.6
C16—C12—C18	118.85 (13)	C42—C37—C38	118.63 (14)
C16—C12—C37	126.41 (13)	C42—C37—C12	122.00 (14)
C18—C12—C37	114.73 (12)	C38—C37—C12	119.08 (14)
C1—C13—C14	119.72 (14)	C39—C38—C37	120.91 (15)
C1—C13—C9	127.11 (13)	C39—C38—H38	119.5
C14—C13—C9	112.83 (13)	C37—C38—H38	119.5
C13—C14—C4	119.85 (14)	C38—C39—C40	119.89 (16)
C13—C14—C10	113.04 (13)	C38—C39—H39	120.1
C4—C14—C10	126.89 (14)	C40—C39—H39	120.1
C11—C15—C16	120.99 (13)	C41—C40—C39	119.89 (15)
C11—C15—C9	127.08 (13)	C41—C40—H40	120.1
C16—C15—C9	111.91 (12)	C39—C40—H40	120.1
C12—C16—C15	120.80 (13)	C40—C41—C42	120.37 (15)
C12—C16—C10	127.73 (13)	C40—C41—H41	119.8
C15—C16—C10	111.43 (12)	C42—C41—H41	119.8
C18—C17—C8	118.69 (13)	C41—C42—C37	120.28 (16)
C18—C17—C11	120.12 (13)	C41—C42—H42	119.9
C8—C17—C11	121.18 (14)	C37—C42—H42	119.9
C17—C18—C5	118.48 (13)	O3—C43—C45	121.95 (18)
C17—C18—C12	120.33 (13)	O3—C43—C44	120.89 (18)
C5—C18—C12	121.18 (14)	C45—C43—C44	117.16 (17)
C24—C19—C20	118.35 (14)	C43—C44—H44A	109.5
C24—C19—C9	120.63 (14)	C43—C44—H44B	109.5
C20—C19—C9	120.95 (14)	H44A—C44—H44B	109.5
C21—C20—C19	120.63 (15)	C43—C44—H44C	109.5
C21—C20—H20	119.7	H44A—C44—H44C	109.5
C19—C20—H20	119.7	H44B—C44—H44C	109.5
C22—C21—C20	120.20 (17)	C43—C45—H45A	109.5
C22—C21—H21	119.9	C43—C45—H45B	109.5
C20—C21—H21	119.9	H45A—C45—H45B	109.5
C21—C22—C23	119.73 (16)	C43—C45—H45C	109.5
C21—C22—H22	120.1	H45A—C45—H45C	109.5
C23—C22—H22	120.1	H45B—C45—H45C	109.5
C24—C23—C22	120.14 (16)

C9—O1—O2—C10	2.79 (14)	C8—C17—C18—C5	1.1 (2)
C13—C1—C2—C3	−3.2 (2)	C11—C17—C18—C5	−179.82 (14)
C1—C2—C3—C4	0.4 (2)	C8—C17—C18—C12	−177.41 (14)
C2—C3—C4—C14	3.1 (2)	C11—C17—C18—C12	1.7 (2)
C18—C5—C6—C7	−0.2 (3)	C6—C5—C18—C17	−0.6 (2)
C5—C6—C7—C8	0.4 (3)	C6—C5—C18—C12	177.93 (15)
C6—C7—C8—C17	0.2 (3)	C16—C12—C18—C17	−0.1 (2)
O2—O1—C9—C19	−177.18 (10)	C37—C12—C18—C17	−179.42 (14)
O2—O1—C9—C13	−58.38 (13)	C16—C12—C18—C5	−178.62 (14)
O2—O1—C9—C15	56.79 (13)	C37—C12—C18—C5	2.1 (2)
O1—O2—C10—C14	55.15 (13)	O1—C9—C19—C24	168.04 (13)
O1—O2—C10—C25	174.28 (10)	C13—C9—C19—C24	55.43 (18)
O1—O2—C10—C16	−60.39 (13)	C15—C9—C19—C24	−76.45 (18)
C2—C1—C13—C14	2.4 (2)	O1—C9—C19—C20	−8.93 (18)
C2—C1—C13—C9	175.14 (14)	C13—C9—C19—C20	−121.53 (15)
O1—C9—C13—C1	−117.38 (15)	C15—C9—C19—C20	106.58 (16)
C19—C9—C13—C1	−6.5 (2)	C24—C19—C20—C21	−1.8 (2)
C15—C9—C13—C1	130.43 (15)	C9—C19—C20—C21	175.27 (13)
O1—C9—C13—C14	55.81 (15)	C19—C20—C21—C22	0.4 (2)
C19—C9—C13—C14	166.65 (12)	C20—C21—C22—C23	1.5 (2)
C15—C9—C13—C14	−56.38 (16)	C21—C22—C23—C24	−1.9 (2)
C1—C13—C14—C4	1.1 (2)	C22—C23—C24—C19	0.5 (2)
C9—C13—C14—C4	−172.63 (13)	C20—C19—C24—C23	1.4 (2)
C1—C13—C14—C10	176.12 (13)	C9—C19—C24—C23	−175.69 (14)
C9—C13—C14—C10	2.37 (17)	O2—C10—C25—C30	9.34 (17)
C3—C4—C14—C13	−3.8 (2)	C14—C10—C25—C30	122.72 (15)
C3—C4—C14—C10	−178.06 (14)	C16—C10—C25—C30	−105.86 (16)
O2—C10—C14—C13	−58.71 (15)	O2—C10—C25—C26	−168.74 (12)
C25—C10—C14—C13	−170.39 (12)	C14—C10—C25—C26	−55.35 (18)
C16—C10—C14—C13	53.53 (16)	C16—C10—C25—C26	76.06 (18)
O2—C10—C14—C4	115.86 (16)	C30—C25—C26—C27	−0.4 (2)
C25—C10—C14—C4	4.2 (2)	C10—C25—C26—C27	177.76 (13)
C16—C10—C14—C4	−131.89 (15)	C25—C26—C27—C28	0.6 (2)
C17—C11—C15—C16	0.0 (2)	C26—C27—C28—C29	−0.1 (2)
C31—C11—C15—C16	−178.71 (14)	C27—C28—C29—C30	−0.5 (2)
C17—C11—C15—C9	−177.93 (14)	C26—C25—C30—C29	−0.2 (2)
C31—C11—C15—C9	3.4 (3)	C10—C25—C30—C29	−178.33 (13)
O1—C9—C15—C11	118.96 (16)	C28—C29—C30—C25	0.6 (2)
C19—C9—C15—C11	4.9 (2)	C15—C11—C31—C32	−79.6 (2)
C13—C9—C15—C11	−128.79 (16)	C17—C11—C31—C32	101.72 (17)
O1—C9—C15—C16	−59.09 (15)	C15—C11—C31—C36	105.37 (18)
C19—C9—C15—C16	−173.12 (13)	C17—C11—C31—C36	−73.35 (18)
C13—C9—C15—C16	53.16 (16)	C36—C31—C32—C33	−2.7 (2)
C18—C12—C16—C15	−1.5 (2)	C11—C31—C32—C33	−177.81 (13)
C37—C12—C16—C15	177.73 (14)	C31—C32—C33—C34	1.4 (2)
C18—C12—C16—C10	176.09 (14)	C32—C33—C34—C35	0.6 (2)
C37—C12—C16—C10	−4.7 (3)	C33—C34—C35—C36	−1.3 (2)
C11—C15—C16—C12	1.6 (2)	C34—C35—C36—C31	0.0 (2)
C9—C15—C16—C12	179.76 (13)	C32—C31—C36—C35	2.0 (2)
C11—C15—C16—C10	−176.35 (13)	C11—C31—C36—C35	177.23 (13)
C9—C15—C16—C10	1.84 (17)	C16—C12—C37—C42	79.8 (2)
O2—C10—C16—C12	−120.29 (16)	C18—C12—C37—C42	−100.95 (16)
C14—C10—C16—C12	126.97 (16)	C16—C12—C37—C38	−106.47 (18)
C25—C10—C16—C12	−6.2 (2)	C18—C12—C37—C38	72.76 (18)
O2—C10—C16—C15	57.46 (15)	C42—C37—C38—C39	−1.5 (2)
C14—C10—C16—C15	−55.28 (16)	C12—C37—C38—C39	−175.42 (14)
C25—C10—C16—C15	171.56 (13)	C37—C38—C39—C40	0.5 (2)
C7—C8—C17—C18	−1.0 (2)	C38—C39—C40—C41	0.1 (2)
C7—C8—C17—C11	180.00 (15)	C39—C40—C41—C42	0.5 (2)
C15—C11—C17—C18	−1.5 (2)	C40—C41—C42—C37	−1.6 (2)
C31—C11—C17—C18	177.27 (14)	C38—C37—C42—C41	2.0 (2)
C15—C11—C17—C8	177.49 (15)	C12—C37—C42—C41	175.78 (13)
C31—C11—C17—C8	−3.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···O3ⁱ	0.95	2.53	3.437 (2)	159
C35—H35···O1ⁱⁱ	0.95	2.59	3.408 (2)	144

Symmetry codes: (i) x−1, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₄₂H₂₈O₂·C₃H₆O
M_r	622.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	90
a, b, c (Å)	11.1592 (6), 21.2248 (11), 13.6121 (7)
β (°)	103.113 (1)
V (Å³)	3140.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.15 × 0.07 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.988, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	20867, 7642, 5257
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.664

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.119, 1.03
No. of reflections	7642
No. of parameters	435
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.29

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009) and ORTEPIII (Burnett & Johnson, 1996), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···O3ⁱ	0.95	2.53	3.437 (2)	159
C35—H35···O1ⁱⁱ	0.95	2.59	3.408 (2)	144

Symmetry codes: (i) x−1, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

References

Brown, C. J. & Ehrenberg, M. (1984). Acta Cryst. C40, 1059–1060. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruker (2007). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Izuoka, A., Murase, T., Tsukada, M., Ito, Y., Sugawara, T., Uchida, A., Sato, N. & Inokuchi, H. (1997). Tetrahedron Lett. 38, 245–248. CSD CrossRef CAS Web of Science Google Scholar
Sakai, K., Ohshima, S., Uchida, A., Oonishi, I., Fujisawa, S. & Nagashima, U. (1995). J. Phys. Chem. 99, 5909–5913. CrossRef CAS Web of Science Google Scholar
Schuster, I. I., Craciun, L., Ho, D. M. & Pascal, R. A. Jr (2002). Tetrahedron, 58, 8875–8882. Web of Science CSD CrossRef CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 68| Part 4| April 2012| Pages o995-o996

doi:10.1107/S1600536812008835

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