9,10-Di­phenyl-9,10-epi­dioxy­anthra­cene and 9,10-di­hydro-10,10-di­methoxy-9-phenyl­anthracen-9-ol

9,10-Di­phenyl-9,10-epi­dioxy­anthracene, C₂₆H₁₈O₂, (I), was accidentally used in a photo­oxy­genation reaction that produced 9,10-di­hydro-10,10-di­methoxy-9-phenyl­anthracen-9-ol, C₂₂H₂₀O₃, (II). In both compounds, the phenyl rings are approximately orthogonal to the anthracene moiety. The conformation of the anthracene moiety differs as a result of substitution. Intramolecular C—H...O interactions in (I) form two approximately planar S(5) rings in each of the two crystallographically independent mol­ecules. The packing of (I) and (II) consists of molecular dimers stabilized by C—H...O interactions and of molecular chains stabilized by O—H...O interactions, respectively.

S1. Comment

9,10-Diphenylanthracene endoperoxide, (I), is a well known chemical source that releases singlet oxygen when heated in benzene and other solvents (Wasserman & Scheffer, 1967). During the course of our investigation of the singlet oxygen reactions of indolizine derivatives (Tian et al., 2001), we refluxed (I) with an indolizine sample in toluene–methanol, with the aim of inducing singlet oxygen reactions, and obtained (II), a phenylanthracene derivative, as one of the products. We have structurally analyzed both (I) and (II), and the results are presented here.

The asymmetric unit of (I) consists of two crystallographically independent molecules, viz. A and B, related by a local pseudo-twofold rotation axis. The bond lengths and bond angles of molecules A and B (Fig. 1) agree with each other and are within normal ranges (Allen et al., 1987).

In both molecules, within the C1–C14 anthracene moiety, the C1—C6—C7—C8—C13—C14 ring exhibits a boat conformation, with atoms C7 and C14 displaced by 0.627 (4) and 0.644 (4) Å, respectively, from the C1/C6/C8/C13 plane in molecule A. The corresponding values in molecule B are 0.659 (4) and 0.644 (4) Å. The two fused benzenze rings, C1–C6 and C8–C13, make dihedral angles with the C1/C6/C8/C13 plane of 21.8 (2) and 19.5 (2)° in molecule A and 26.1 (2) and 23.4 (2)° in molecule B. The C1/C6/C8/C13 plane is orthogonal to the C7/O2/O1/C14 plane, with the dihedral angle between the two planes being 89.7 (2) and 89.9 (2)° in molecules A and B, respectively.

The C7/O2/O1/C14 plane is approximately coplanar with the C15–C20 and C21–C26 phenyl rings, with dihedral angles of 5.3 (2) and 2.3 (2)° in molecule A and 4.6 (2) and 1.6 (1)° in molecule B. This coplanarity is maintained by intramolecular C16—H16···O1 and C26—H26···O2 interactions, which form O1—C14—C15—C16—H16 and O2—C7—C21—C26—H26 S(5) graph-set rings (Etter et al., 1990) in both molecules (Fig. 1). The dihedral angles differ between molecules A and B because atom O1 in molecule A facilitates an intermolecular interaction, in which C17B—H17B···O1Aⁱ interactions connect A and B molecules from different asymmetric units into dimers.

In contrast to (I),the anthracene moiety of (II) is planar to within ±0.042 (3) Å. An intramolecular C16—H16···O1 interaction, similar to the intermolecular interactions in (I), forms an O1—C14—C15—C16—H16 S(5) graph-set ring. This ring is slightly non-planar, with a O1—C14—C15—C16 torsion angle of 21.8 (3)°. In (II), the two methoxy groups attached to atom C7 are coplanar. Both the C21/O2/C7/O3/C22 plane and the C15–C20 phenyl ring are orthogonal to the anthracene moiety, with dihedral angles of 89.8 (2) and 81.3 (1)°, repectively. The packing is comprises molecular chains along the b direction (Fig. 3), stabilized by by O1—H1O1···O3ⁱ interactions.

S2. Experimental

Compound (I) was prepared by methylene blue-sensitized photooxygenation with 9,10-diphenylanthracene and was separated by column chromatography on silica gel with petroleum ether and ethyl acetate eluants. Compound (II) was accidentally obtained by refluxing a tolene–methanol solution of 1-(4-methoxybenzoyl)-2-phenylindolizine with (I). Compound (II) was also separated by column chromatography on silica gel with petroleum ether and ethyl acetate as eluents. Single crystals of (I) and (II) were obtained from slow evaporation of their petroleum ether/ethyl acetate solutions.

S3. Refinement

The H atoms of (I) were fixed geometrically and treated as riding on their parent C atoms, with C—H distances of 0.96 Å and U_iso(H) values of 1.5 U_eq(C). For (II), H atoms were located in difference maps and were refined isotropically, except for H atoms attached to atoms C21 and C22, which were fixed geometrically and treated as riding atoms, with C—H distances of 0.93 Å and U_iso(H) values of 1.2 U_eq(C). A rotating group refinement was used for the methyl groups. Owing to the large number of weak data at higher angles, the 2θ maximum was limited to 50° for both (I) and (II).

Computing details

For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996). Data reduction: SAINT and SADABS (Sheldrick, 1996) for (I); SAINT and SADABS for (II). For both compounds, program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures

	Fig. 1. A view of the structure of (I), showing displacement ellipsoids at the 50% probability level and the atom-numbering scheme. All H atoms have been omitted for the sake of clarity.
	Fig. 2. A view of the structure of (II), showing displacement ellipsoids at the 50% probability level and the atom-numbering scheme. All H atoms have been omitted for the sake of clarity.
	Fig. 3. Packing diagram of (II), showing chains parallel to the b direction. All H atoms attached to C atoms have been omitted for clarity. Dashed lines denote intermolecular O—H···O interactions.

(I) 9,10-Diphenylanthracene endoperoxide (I)

Crystal data

C26H18O2	Dx = 1.289 Mg m^−3
Mr = 362.40	Melting point: 517(2)K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.8390 (12) Å	Cell parameters from 3581 reflections
b = 10.4950 (6) Å	θ = 2.3–28.3°
c = 18.013 (1) Å	µ = 0.08 mm^−1
β = 95.016 (1)°	T = 293 K
V = 3736.1 (4) Å^3	Cylindrical, colorless
Z = 8	0.46 × 0.20 × 0.16 mm
F(000) = 1520

Data collection

Siemens SMART CCD area detector diffractometer	3917 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
Detector resolution: 8.33 pixels mm^-1	h = −20→23
ω scans	k = −12→12
18226 measured reflections	l = −18→21
6575 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.091	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.218	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0783P)^2 + 6.3806P] where P = (Fo^2 + 2Fc^2)/3
6575 reflections	(Δ/σ)max < 0.001
505 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.13283 (14)	0.3287 (3)	0.26578 (16)	0.0288 (7)
O2A	0.07838 (15)	0.2658 (3)	0.21721 (17)	0.0355 (8)
C1A	0.1383 (2)	0.1474 (4)	0.3441 (2)	0.0241 (10)
C2A	0.1411 (2)	0.1314 (4)	0.4200 (2)	0.0306 (11)
H2A	0.1746	0.1720	0.4506	0.037*
C3A	0.0941 (2)	0.0554 (5)	0.4510 (3)	0.0376 (12)
H3A	0.0964	0.0437	0.5024	0.045*
C4A	0.0443 (2)	−0.0026 (5)	0.4059 (3)	0.0406 (13)
H4A	0.0128	−0.0540	0.4270	0.049*
C5A	0.0397 (2)	0.0137 (4)	0.3292 (3)	0.0340 (11)
H5A	0.0050	−0.0247	0.2991	0.041*
C6A	0.0875 (2)	0.0880 (4)	0.2981 (2)	0.0235 (10)
C7A	0.0880 (2)	0.1262 (4)	0.2169 (2)	0.0295 (11)
C8A	0.1574 (2)	0.1070 (4)	0.1899 (2)	0.0273 (10)
C9A	0.1708 (3)	0.0539 (5)	0.1228 (3)	0.0398 (13)
H9A	0.1363	0.0174	0.0915	0.048*
C10A	0.2370 (3)	0.0561 (5)	0.1029 (3)	0.0532 (15)
H10A	0.2470	0.0190	0.0583	0.064*
C11A	0.2875 (3)	0.1119 (5)	0.1480 (3)	0.0538 (16)
H11A	0.3314	0.1136	0.1336	0.065*
C12A	0.2736 (2)	0.1662 (5)	0.2153 (3)	0.0411 (13)
H12A	0.3080	0.2035	0.2464	0.049*
C13A	0.2079 (2)	0.1640 (4)	0.2356 (2)	0.0262 (10)
C14A	0.1811 (2)	0.2348 (4)	0.3006 (2)	0.0265 (10)
C15A	0.2338 (2)	0.3128 (4)	0.3472 (2)	0.0294 (11)
C16A	0.2353 (2)	0.4432 (4)	0.3464 (3)	0.0376 (12)
H16A	0.2027	0.4881	0.3168	0.045*
C17A	0.2849 (3)	0.5082 (5)	0.3894 (3)	0.0454 (14)
H17A	0.2853	0.5968	0.3888	0.054*
C18A	0.3339 (3)	0.4433 (5)	0.4331 (3)	0.0463 (14)
H18A	0.3667	0.4876	0.4628	0.056*
C19A	0.3338 (3)	0.3129 (5)	0.4324 (3)	0.0484 (14)
H19A	0.3673	0.2684	0.4610	0.058*
C20A	0.2842 (2)	0.2468 (5)	0.3898 (3)	0.0425 (13)
H20A	0.2845	0.1582	0.3895	0.051*
C21A	0.0300 (2)	0.0730 (5)	0.1666 (2)	0.0310 (11)
C22A	0.0280 (2)	−0.0576 (5)	0.1544 (3)	0.0403 (12)
H22A	0.0613	−0.1088	0.1785	0.048*
C23A	−0.0218 (3)	−0.1133 (6)	0.1076 (3)	0.0512 (15)
H23A	−0.0217	−0.2010	0.1000	0.061*
C24A	−0.0709 (3)	−0.0404 (7)	0.0727 (3)	0.0623 (18)
H24A	−0.1044	−0.0775	0.0403	0.075*
C25A	−0.0712 (3)	0.0891 (7)	0.0852 (4)	0.076 (2)
H25A	−0.1060	0.1386	0.0624	0.091*
C26A	−0.0201 (3)	0.1468 (6)	0.1316 (3)	0.0586 (16)
H26A	−0.0200	0.2346	0.1386	0.070*
O1B	0.35396 (15)	1.0064 (3)	0.49269 (16)	0.0328 (8)
O2B	0.40953 (16)	1.0017 (3)	0.44279 (17)	0.0387 (8)
C1B	0.2935 (2)	0.8593 (4)	0.4112 (2)	0.0246 (10)
C2B	0.2271 (2)	0.8487 (4)	0.3799 (2)	0.0323 (11)
H2B	0.1912	0.8573	0.4094	0.039*
C3B	0.2151 (2)	0.8253 (5)	0.3045 (3)	0.0401 (13)
H3B	0.1710	0.8149	0.2836	0.048*
C4B	0.2675 (3)	0.8175 (5)	0.2604 (3)	0.0476 (14)
H4B	0.2586	0.8024	0.2096	0.057*
C5B	0.3340 (3)	0.8318 (5)	0.2906 (3)	0.0387 (12)
H5B	0.3693	0.8278	0.2600	0.046*
C6B	0.3472 (2)	0.8518 (4)	0.3661 (2)	0.0267 (10)
C7B	0.4153 (2)	0.8748 (4)	0.4093 (2)	0.0283 (10)
C8B	0.4244 (2)	0.7823 (4)	0.4747 (2)	0.0258 (10)
C9B	0.4802 (2)	0.7077 (5)	0.4953 (3)	0.0343 (12)
H9B	0.5170	0.7067	0.4666	0.041*
C10B	0.4809 (2)	0.6348 (5)	0.5588 (3)	0.0395 (12)
H10B	0.5181	0.5833	0.5724	0.047*
C11B	0.4278 (3)	0.6370 (5)	0.6024 (3)	0.0417 (13)
H11B	0.4290	0.5870	0.6451	0.050*
C12B	0.3718 (2)	0.7142 (5)	0.5827 (2)	0.0334 (11)
H12B	0.3358	0.7168	0.6125	0.040*
C13B	0.3704 (2)	0.7867 (4)	0.5186 (2)	0.0261 (10)
C14B	0.3174 (2)	0.8836 (4)	0.4922 (2)	0.0280 (10)
C15B	0.2619 (2)	0.9033 (4)	0.5433 (2)	0.0304 (11)
C16B	0.2549 (3)	1.0144 (5)	0.5836 (3)	0.0428 (13)
H16B	0.2853	1.0809	0.5794	0.051*
C17B	0.2038 (3)	1.0274 (6)	0.6296 (3)	0.0551 (16)
H17B	0.1998	1.1030	0.6558	0.066*
C18B	0.1588 (3)	0.9312 (7)	0.6375 (3)	0.0540 (16)
H18B	0.1246	0.9406	0.6693	0.065*
C19B	0.1644 (3)	0.8192 (5)	0.5978 (3)	0.0456 (14)
H19B	0.1334	0.7538	0.6021	0.055*
C20B	0.2160 (2)	0.8047 (5)	0.5517 (3)	0.0374 (12)
H20B	0.2202	0.7286	0.5261	0.045*
C21B	0.4742 (2)	0.8850 (5)	0.3612 (2)	0.0314 (11)
C22B	0.4915 (2)	0.7789 (5)	0.3203 (3)	0.0420 (13)
H22B	0.4675	0.7033	0.3239	0.050*
C23B	0.5436 (3)	0.7847 (5)	0.2748 (3)	0.0482 (14)
H23B	0.5547	0.7129	0.2481	0.058*
C24B	0.5792 (3)	0.8954 (6)	0.2685 (3)	0.0520 (15)
H24B	0.6134	0.9000	0.2364	0.062*
C25B	0.5639 (3)	0.9997 (6)	0.3101 (3)	0.0509 (14)
H25B	0.5889	1.0743	0.3073	0.061*
C26B	0.5116 (2)	0.9945 (5)	0.3559 (3)	0.0415 (13)
H26B	0.5016	1.0658	0.3836	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0329 (17)	0.0181 (17)	0.0351 (18)	0.0008 (13)	0.0015 (14)	0.0012 (13)
O2A	0.0376 (19)	0.0261 (18)	0.0413 (19)	0.0023 (15)	−0.0057 (15)	0.0055 (15)
C1A	0.025 (2)	0.019 (2)	0.029 (2)	0.0064 (19)	0.0062 (19)	−0.0002 (19)
C2A	0.031 (3)	0.031 (3)	0.029 (3)	0.006 (2)	0.001 (2)	0.006 (2)
C3A	0.043 (3)	0.043 (3)	0.028 (3)	0.011 (3)	0.013 (2)	0.008 (2)
C4A	0.038 (3)	0.042 (3)	0.045 (3)	−0.001 (2)	0.018 (2)	0.010 (3)
C5A	0.029 (3)	0.036 (3)	0.039 (3)	−0.006 (2)	0.012 (2)	−0.002 (2)
C6A	0.018 (2)	0.020 (2)	0.033 (2)	−0.0002 (18)	0.0046 (19)	−0.0008 (19)
C7A	0.036 (3)	0.021 (3)	0.032 (3)	0.000 (2)	0.003 (2)	0.004 (2)
C8A	0.033 (3)	0.024 (3)	0.026 (2)	0.001 (2)	0.011 (2)	0.0043 (19)
C9A	0.048 (3)	0.041 (3)	0.033 (3)	−0.007 (2)	0.013 (2)	−0.007 (2)
C10A	0.054 (4)	0.057 (4)	0.053 (3)	−0.008 (3)	0.028 (3)	−0.016 (3)
C11A	0.040 (3)	0.059 (4)	0.067 (4)	−0.001 (3)	0.034 (3)	−0.013 (3)
C12A	0.033 (3)	0.033 (3)	0.059 (3)	−0.004 (2)	0.014 (2)	−0.009 (3)
C13A	0.025 (2)	0.021 (2)	0.034 (3)	0.0037 (19)	0.007 (2)	0.004 (2)
C14A	0.023 (2)	0.021 (2)	0.036 (3)	0.0064 (19)	0.005 (2)	0.003 (2)
C15A	0.029 (3)	0.026 (3)	0.035 (3)	0.000 (2)	0.012 (2)	−0.001 (2)
C16A	0.044 (3)	0.023 (3)	0.046 (3)	0.002 (2)	0.006 (2)	0.002 (2)
C17A	0.050 (3)	0.032 (3)	0.055 (3)	−0.009 (3)	0.007 (3)	−0.014 (3)
C18A	0.039 (3)	0.049 (4)	0.050 (3)	−0.014 (3)	−0.003 (3)	−0.019 (3)
C19A	0.034 (3)	0.048 (4)	0.062 (4)	−0.008 (3)	−0.003 (3)	−0.004 (3)
C20A	0.038 (3)	0.029 (3)	0.059 (3)	0.001 (2)	0.000 (3)	0.004 (3)
C21A	0.027 (3)	0.036 (3)	0.030 (3)	−0.004 (2)	0.002 (2)	0.003 (2)
C22A	0.029 (3)	0.047 (3)	0.044 (3)	−0.004 (2)	−0.003 (2)	0.000 (2)
C23A	0.051 (3)	0.063 (4)	0.039 (3)	−0.021 (3)	0.002 (3)	−0.006 (3)
C24A	0.060 (4)	0.077 (5)	0.045 (3)	−0.027 (4)	−0.017 (3)	0.007 (3)
C25A	0.059 (4)	0.084 (6)	0.079 (5)	0.003 (4)	−0.031 (4)	0.016 (4)
C26A	0.053 (4)	0.051 (4)	0.068 (4)	0.004 (3)	−0.016 (3)	0.012 (3)
O1B	0.0371 (19)	0.0271 (18)	0.0359 (18)	0.0000 (15)	0.0131 (15)	−0.0093 (14)
O2B	0.044 (2)	0.0300 (19)	0.044 (2)	−0.0041 (16)	0.0150 (16)	−0.0064 (15)
C1B	0.034 (3)	0.015 (2)	0.024 (2)	0.0062 (19)	0.001 (2)	0.0006 (18)
C2B	0.031 (3)	0.030 (3)	0.035 (3)	0.008 (2)	0.000 (2)	−0.003 (2)
C3B	0.035 (3)	0.054 (3)	0.030 (3)	0.004 (2)	−0.008 (2)	−0.004 (2)
C4B	0.050 (3)	0.069 (4)	0.023 (3)	0.001 (3)	−0.003 (2)	0.000 (3)
C5B	0.042 (3)	0.045 (3)	0.029 (3)	−0.001 (2)	0.007 (2)	0.002 (2)
C6B	0.039 (3)	0.018 (2)	0.023 (2)	0.003 (2)	0.006 (2)	−0.0010 (18)
C7B	0.030 (3)	0.025 (3)	0.029 (2)	0.000 (2)	0.001 (2)	−0.005 (2)
C8B	0.028 (2)	0.022 (2)	0.027 (2)	−0.005 (2)	−0.001 (2)	−0.0047 (19)
C9B	0.023 (2)	0.044 (3)	0.037 (3)	0.002 (2)	0.006 (2)	−0.002 (2)
C10B	0.034 (3)	0.038 (3)	0.046 (3)	0.011 (2)	−0.001 (2)	0.002 (2)
C11B	0.048 (3)	0.045 (3)	0.030 (3)	0.009 (3)	−0.004 (2)	0.007 (2)
C12B	0.036 (3)	0.041 (3)	0.024 (2)	0.000 (2)	0.003 (2)	0.000 (2)
C13B	0.027 (2)	0.031 (3)	0.020 (2)	−0.003 (2)	−0.0012 (19)	−0.0132 (19)
C14B	0.037 (3)	0.020 (2)	0.028 (2)	0.000 (2)	0.005 (2)	−0.0061 (19)
C15B	0.038 (3)	0.032 (3)	0.021 (2)	0.009 (2)	0.001 (2)	0.001 (2)
C16B	0.042 (3)	0.047 (3)	0.039 (3)	0.007 (3)	0.002 (2)	−0.017 (3)
C17B	0.056 (4)	0.069 (4)	0.043 (3)	0.007 (3)	0.021 (3)	−0.026 (3)
C18B	0.045 (3)	0.092 (5)	0.027 (3)	0.023 (3)	0.012 (2)	0.004 (3)
C19B	0.038 (3)	0.057 (4)	0.042 (3)	0.004 (3)	0.006 (3)	0.013 (3)
C20B	0.039 (3)	0.038 (3)	0.037 (3)	0.004 (2)	0.010 (2)	0.004 (2)
C21B	0.029 (3)	0.041 (3)	0.024 (2)	0.001 (2)	0.002 (2)	−0.003 (2)
C22B	0.038 (3)	0.042 (3)	0.048 (3)	−0.003 (2)	0.014 (3)	−0.008 (3)
C23B	0.043 (3)	0.051 (4)	0.053 (3)	0.000 (3)	0.015 (3)	−0.002 (3)
C24B	0.039 (3)	0.073 (4)	0.046 (3)	0.006 (3)	0.014 (3)	0.013 (3)
C25B	0.045 (3)	0.048 (4)	0.061 (4)	−0.007 (3)	0.014 (3)	0.000 (3)
C26B	0.039 (3)	0.043 (3)	0.044 (3)	−0.005 (3)	0.010 (2)	−0.004 (2)

Geometric parameters (Å, º)

O1A—C14A	1.476 (5)	O1B—C14B	1.478 (5)
O1A—O2A	1.485 (4)	O1B—O2B	1.483 (4)
O2A—C7A	1.477 (5)	O2B—C7B	1.471 (5)
C1A—C2A	1.374 (6)	C1B—C2B	1.390 (6)
C1A—C6A	1.394 (6)	C1B—C6B	1.399 (6)
C1A—C14A	1.516 (6)	C1B—C14B	1.516 (6)
C2A—C3A	1.381 (6)	C2B—C3B	1.380 (6)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.367 (7)	C3B—C4B	1.365 (7)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.388 (6)	C4B—C5B	1.390 (7)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.383 (6)	C5B—C6B	1.379 (6)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.518 (6)	C6B—C7B	1.519 (6)
C7A—C21A	1.509 (6)	C7B—C21B	1.518 (6)
C7A—C8A	1.513 (6)	C7B—C8B	1.524 (6)
C8A—C13A	1.377 (6)	C8B—C9B	1.381 (6)
C8A—C9A	1.377 (6)	C8B—C13B	1.386 (6)
C9A—C10A	1.392 (7)	C9B—C10B	1.376 (6)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.366 (7)	C10B—C11B	1.367 (7)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.389 (7)	C11B—C12B	1.395 (6)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.385 (6)	C12B—C13B	1.382 (6)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.520 (6)	C13B—C14B	1.510 (6)
C14A—C15A	1.521 (6)	C14B—C15B	1.511 (6)
C15A—C16A	1.368 (6)	C15B—C16B	1.387 (6)
C15A—C20A	1.391 (6)	C15B—C20B	1.394 (6)
C16A—C17A	1.378 (7)	C16B—C17B	1.371 (7)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.377 (7)	C17B—C18B	1.364 (8)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C19A	1.368 (7)	C18B—C19B	1.386 (8)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.380 (7)	C19B—C20B	1.381 (7)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—C26A	1.369 (7)	C21B—C26B	1.376 (6)
C21A—C22A	1.389 (7)	C21B—C22B	1.395 (6)
C22A—C23A	1.370 (7)	C22B—C23B	1.376 (7)
C22A—H22A	0.9300	C22B—H22B	0.9300
C23A—C24A	1.351 (8)	C23B—C24B	1.370 (8)
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—C25A	1.378 (9)	C24B—C25B	1.376 (8)
C24A—H24A	0.9300	C24B—H24B	0.9300
C25A—C26A	1.396 (8)	C25B—C26B	1.382 (7)
C25A—H25A	0.9300	C25B—H25B	0.9300
C26A—H26A	0.9300	C26B—H26B	0.9300
C14A—O1A—O2A	111.4 (3)	C14B—O1B—O2B	111.0 (3)
C7A—O2A—O1A	110.8 (3)	C7B—O2B—O1B	111.5 (3)
C2A—C1A—C6A	120.0 (4)	C2B—C1B—C6B	120.1 (4)
C2A—C1A—C14A	127.8 (4)	C2B—C1B—C14B	127.6 (4)
C6A—C1A—C14A	111.9 (4)	C6B—C1B—C14B	112.2 (4)
C1A—C2A—C3A	120.2 (4)	C3B—C2B—C1B	119.3 (4)
C1A—C2A—H2A	119.9	C3B—C2B—H2B	120.3
C3A—C2A—H2A	119.9	C1B—C2B—H2B	120.3
C4A—C3A—C2A	119.7 (4)	C4B—C3B—C2B	120.6 (5)
C4A—C3A—H3A	120.2	C4B—C3B—H3B	119.7
C2A—C3A—H3A	120.2	C2B—C3B—H3B	119.7
C3A—C4A—C5A	121.2 (5)	C3B—C4B—C5B	120.7 (5)
C3A—C4A—H4A	119.4	C3B—C4B—H4B	119.7
C5A—C4A—H4A	119.4	C5B—C4B—H4B	119.7
C6A—C5A—C4A	119.0 (4)	C6B—C5B—C4B	119.6 (4)
C6A—C5A—H5A	120.5	C6B—C5B—H5B	120.2
C4A—C5A—H5A	120.5	C4B—C5B—H5B	120.2
C5A—C6A—C1A	119.9 (4)	C5B—C6B—C1B	119.5 (4)
C5A—C6A—C7A	126.9 (4)	C5B—C6B—C7B	127.9 (4)
C1A—C6A—C7A	112.9 (4)	C1B—C6B—C7B	112.4 (4)
O2A—C7A—C21A	106.1 (4)	O2B—C7B—C21B	105.1 (3)
O2A—C7A—C8A	104.8 (3)	O2B—C7B—C6B	104.9 (3)
C21A—C7A—C8A	115.1 (4)	C21B—C7B—C6B	114.4 (3)
O2A—C7A—C6A	104.3 (3)	O2B—C7B—C8B	105.6 (3)
C21A—C7A—C6A	114.3 (4)	C21B—C7B—C8B	116.2 (4)
C8A—C7A—C6A	111.0 (4)	C6B—C7B—C8B	109.6 (4)
C13A—C8A—C9A	121.0 (4)	C9B—C8B—C13B	120.5 (4)
C13A—C8A—C7A	112.6 (4)	C9B—C8B—C7B	127.3 (4)
C9A—C8A—C7A	126.0 (4)	C13B—C8B—C7B	112.0 (4)
C8A—C9A—C10A	118.6 (5)	C10B—C9B—C8B	119.2 (4)
C8A—C9A—H9A	120.7	C10B—C9B—H9B	120.4
C10A—C9A—H9A	120.7	C8B—C9B—H9B	120.4
C11A—C10A—C9A	120.9 (5)	C11B—C10B—C9B	121.1 (5)
C11A—C10A—H10A	119.5	C11B—C10B—H10B	119.4
C9A—C10A—H10A	119.5	C9B—C10B—H10B	119.4
C10A—C11A—C12A	120.2 (5)	C10B—C11B—C12B	120.0 (5)
C10A—C11A—H11A	119.9	C10B—C11B—H11B	120.0
C12A—C11A—H11A	119.9	C12B—C11B—H11B	120.0
C13A—C12A—C11A	119.1 (5)	C13B—C12B—C11B	119.3 (4)
C13A—C12A—H12A	120.4	C13B—C12B—H12B	120.3
C11A—C12A—H12A	120.4	C11B—C12B—H12B	120.3
C8A—C13A—C12A	120.2 (4)	C12B—C13B—C8B	119.9 (4)
C8A—C13A—C14A	112.9 (4)	C12B—C13B—C14B	126.6 (4)
C12A—C13A—C14A	126.5 (4)	C8B—C13B—C14B	113.2 (4)
O1A—C14A—C1A	104.6 (3)	O1B—C14B—C13B	104.9 (3)
O1A—C14A—C13A	104.9 (3)	O1B—C14B—C15B	105.1 (3)
C1A—C14A—C13A	110.6 (3)	C13B—C14B—C15B	115.2 (4)
O1A—C14A—C15A	105.3 (3)	O1B—C14B—C1B	105.3 (3)
C1A—C14A—C15A	115.4 (4)	C13B—C14B—C1B	109.9 (3)
C13A—C14A—C15A	114.8 (4)	C15B—C14B—C1B	115.2 (4)
C16A—C15A—C20A	119.2 (5)	C16B—C15B—C20B	118.1 (4)
C16A—C15A—C14A	123.1 (4)	C16B—C15B—C14B	123.1 (4)
C20A—C15A—C14A	117.6 (4)	C20B—C15B—C14B	118.8 (4)
C15A—C16A—C17A	120.3 (5)	C17B—C16B—C15B	120.9 (5)
C15A—C16A—H16A	119.9	C17B—C16B—H16B	119.6
C17A—C16A—H16A	119.9	C15B—C16B—H16B	119.6
C18A—C17A—C16A	120.7 (5)	C18B—C17B—C16B	120.9 (5)
C18A—C17A—H17A	119.7	C18B—C17B—H17B	119.5
C16A—C17A—H17A	119.7	C16B—C17B—H17B	119.5
C19A—C18A—C17A	119.3 (5)	C17B—C18B—C19B	119.4 (5)
C19A—C18A—H18A	120.4	C17B—C18B—H18B	120.3
C17A—C18A—H18A	120.4	C19B—C18B—H18B	120.3
C18A—C19A—C20A	120.5 (5)	C20B—C19B—C18B	120.1 (5)
C18A—C19A—H19A	119.7	C20B—C19B—H19B	120.0
C20A—C19A—H19A	119.7	C18B—C19B—H19B	120.0
C19A—C20A—C15A	120.0 (5)	C19B—C20B—C15B	120.5 (5)
C19A—C20A—H20A	120.0	C19B—C20B—H20B	119.7
C15A—C20A—H20A	120.0	C15B—C20B—H20B	119.7
C26A—C21A—C22A	118.4 (5)	C26B—C21B—C22B	118.1 (4)
C26A—C21A—C7A	123.5 (5)	C26B—C21B—C7B	123.1 (4)
C22A—C21A—C7A	118.1 (4)	C22B—C21B—C7B	118.8 (4)
C23A—C22A—C21A	121.8 (5)	C23B—C22B—C21B	120.8 (5)
C23A—C22A—H22A	119.1	C23B—C22B—H22B	119.6
C21A—C22A—H22A	119.1	C21B—C22B—H22B	119.6
C24A—C23A—C22A	119.8 (6)	C24B—C23B—C22B	120.4 (5)
C24A—C23A—H23A	120.1	C24B—C23B—H23B	119.8
C22A—C23A—H23A	120.1	C22B—C23B—H23B	119.8
C23A—C24A—C25A	119.7 (6)	C23B—C24B—C25B	119.3 (5)
C23A—C24A—H24A	120.1	C23B—C24B—H24B	120.3
C25A—C24A—H24A	120.1	C25B—C24B—H24B	120.3
C24A—C25A—C26A	120.8 (6)	C24B—C25B—C26B	120.5 (5)
C24A—C25A—H25A	119.6	C24B—C25B—H25B	119.8
C26A—C25A—H25A	119.6	C26B—C25B—H25B	119.8
C21A—C26A—C25A	119.4 (6)	C21B—C26B—C25B	120.8 (5)
C21A—C26A—H26A	120.3	C21B—C26B—H26B	119.6
C25A—C26A—H26A	120.3	C25B—C26B—H26B	119.6
C14A—O1A—O2A—C7A	−0.3 (4)	C14B—O1B—O2B—C7B	−2.8 (4)
C6A—C1A—C2A—C3A	0.8 (6)	C6B—C1B—C2B—C3B	2.7 (7)
C14A—C1A—C2A—C3A	174.4 (4)	C14B—C1B—C2B—C3B	−179.5 (4)
C1A—C2A—C3A—C4A	−0.9 (7)	C1B—C2B—C3B—C4B	−2.5 (7)
C2A—C3A—C4A—C5A	−0.2 (7)	C2B—C3B—C4B—C5B	0.5 (8)
C3A—C4A—C5A—C6A	1.4 (7)	C3B—C4B—C5B—C6B	1.2 (8)
C4A—C5A—C6A—C1A	−1.5 (7)	C4B—C5B—C6B—C1B	−0.9 (7)
C4A—C5A—C6A—C7A	−174.6 (4)	C4B—C5B—C6B—C7B	−177.4 (5)
C2A—C1A—C6A—C5A	0.4 (6)	C2B—C1B—C6B—C5B	−1.0 (6)
C14A—C1A—C6A—C5A	−174.1 (4)	C14B—C1B—C6B—C5B	−179.1 (4)
C2A—C1A—C6A—C7A	174.4 (4)	C2B—C1B—C6B—C7B	176.0 (4)
C14A—C1A—C6A—C7A	−0.2 (5)	C14B—C1B—C6B—C7B	−2.1 (5)
O1A—O2A—C7A—C21A	179.6 (3)	O1B—O2B—C7B—C21B	−179.3 (3)
O1A—O2A—C7A—C8A	−58.2 (4)	O1B—O2B—C7B—C6B	59.8 (4)
O1A—O2A—C7A—C6A	58.6 (4)	O1B—O2B—C7B—C8B	−56.0 (4)
C5A—C6A—C7A—O2A	114.0 (5)	C5B—C6B—C7B—O2B	119.0 (5)
C1A—C6A—C7A—O2A	−59.4 (4)	C1B—C6B—C7B—O2B	−57.7 (4)
C5A—C6A—C7A—C21A	−1.3 (6)	C5B—C6B—C7B—C21B	4.4 (7)
C1A—C6A—C7A—C21A	−174.8 (4)	C1B—C6B—C7B—C21B	−172.3 (4)
C5A—C6A—C7A—C8A	−133.6 (5)	C5B—C6B—C7B—C8B	−128.1 (5)
C1A—C6A—C7A—C8A	52.9 (5)	C1B—C6B—C7B—C8B	55.2 (5)
O2A—C7A—C8A—C13A	60.2 (4)	O2B—C7B—C8B—C9B	−115.5 (5)
C21A—C7A—C8A—C13A	176.4 (4)	C21B—C7B—C8B—C9B	0.5 (6)
C6A—C7A—C8A—C13A	−51.8 (5)	C6B—C7B—C8B—C9B	132.0 (5)
O2A—C7A—C8A—C9A	−111.7 (5)	O2B—C7B—C8B—C13B	59.3 (4)
C21A—C7A—C8A—C9A	4.4 (6)	C21B—C7B—C8B—C13B	175.3 (4)
C6A—C7A—C8A—C9A	136.3 (5)	C6B—C7B—C8B—C13B	−53.1 (5)
C13A—C8A—C9A—C10A	1.7 (7)	C13B—C8B—C9B—C10B	1.9 (7)
C7A—C8A—C9A—C10A	172.9 (5)	C7B—C8B—C9B—C10B	176.3 (4)
C8A—C9A—C10A—C11A	−1.4 (8)	C8B—C9B—C10B—C11B	−1.2 (7)
C9A—C10A—C11A—C12A	0.9 (9)	C9B—C10B—C11B—C12B	−0.2 (8)
C10A—C11A—C12A—C13A	−0.6 (8)	C10B—C11B—C12B—C13B	0.8 (7)
C9A—C8A—C13A—C12A	−1.4 (7)	C11B—C12B—C13B—C8B	−0.1 (7)
C7A—C8A—C13A—C12A	−173.8 (4)	C11B—C12B—C13B—C14B	−174.3 (4)
C9A—C8A—C13A—C14A	170.8 (4)	C9B—C8B—C13B—C12B	−1.2 (6)
C7A—C8A—C13A—C14A	−1.5 (5)	C7B—C8B—C13B—C12B	−176.5 (4)
C11A—C12A—C13A—C8A	0.9 (7)	C9B—C8B—C13B—C14B	173.7 (4)
C11A—C12A—C13A—C14A	−170.2 (5)	C7B—C8B—C13B—C14B	−1.5 (5)
O2A—O1A—C14A—C1A	−58.7 (4)	O2B—O1B—C14B—C13B	59.5 (4)
O2A—O1A—C14A—C13A	57.7 (4)	O2B—O1B—C14B—C15B	−178.6 (3)
O2A—O1A—C14A—C15A	179.2 (3)	O2B—O1B—C14B—C1B	−56.5 (4)
C2A—C1A—C14A—O1A	−114.5 (5)	C12B—C13B—C14B—O1B	116.7 (5)
C6A—C1A—C14A—O1A	59.5 (4)	C8B—C13B—C14B—O1B	−57.9 (4)
C2A—C1A—C14A—C13A	133.0 (4)	C12B—C13B—C14B—C15B	1.6 (6)
C6A—C1A—C14A—C13A	−52.9 (5)	C8B—C13B—C14B—C15B	−173.0 (4)
C2A—C1A—C14A—C15A	0.7 (6)	C12B—C13B—C14B—C1B	−130.5 (4)
C6A—C1A—C14A—C15A	174.7 (4)	C8B—C13B—C14B—C1B	54.9 (5)
C8A—C13A—C14A—O1A	−57.7 (4)	C2B—C1B—C14B—O1B	−117.9 (4)
C12A—C13A—C14A—O1A	114.0 (5)	C6B—C1B—C14B—O1B	60.0 (4)
C8A—C13A—C14A—C1A	54.5 (5)	C2B—C1B—C14B—C13B	129.6 (5)
C12A—C13A—C14A—C1A	−133.9 (5)	C6B—C1B—C14B—C13B	−52.5 (5)
C8A—C13A—C14A—C15A	−172.8 (4)	C2B—C1B—C14B—C15B	−2.5 (6)
C12A—C13A—C14A—C15A	−1.2 (6)	C6B—C1B—C14B—C15B	175.4 (4)
O1A—C14A—C15A—C16A	−6.2 (6)	O1B—C14B—C15B—C16B	−4.2 (6)
C1A—C14A—C15A—C16A	−121.0 (5)	C13B—C14B—C15B—C16B	110.7 (5)
C13A—C14A—C15A—C16A	108.7 (5)	C1B—C14B—C15B—C16B	−119.7 (5)
O1A—C14A—C15A—C20A	176.6 (4)	O1B—C14B—C15B—C20B	177.0 (4)
C1A—C14A—C15A—C20A	61.9 (5)	C13B—C14B—C15B—C20B	−68.1 (5)
C13A—C14A—C15A—C20A	−68.5 (5)	C1B—C14B—C15B—C20B	61.5 (5)
C20A—C15A—C16A—C17A	−2.1 (7)	C20B—C15B—C16B—C17B	−0.8 (7)
C14A—C15A—C16A—C17A	−179.2 (4)	C14B—C15B—C16B—C17B	−179.6 (5)
C15A—C16A—C17A—C18A	0.5 (8)	C15B—C16B—C17B—C18B	0.6 (8)
C16A—C17A—C18A—C19A	1.3 (8)	C16B—C17B—C18B—C19B	−0.7 (8)
C17A—C18A—C19A—C20A	−1.5 (8)	C17B—C18B—C19B—C20B	1.2 (8)
C18A—C19A—C20A—C15A	−0.2 (8)	C18B—C19B—C20B—C15B	−1.6 (7)
C16A—C15A—C20A—C19A	2.0 (7)	C16B—C15B—C20B—C19B	1.3 (7)
C14A—C15A—C20A—C19A	179.2 (4)	C14B—C15B—C20B—C19B	−179.8 (4)
O2A—C7A—C21A—C26A	−1.0 (6)	O2B—C7B—C21B—C26B	1.5 (6)
C8A—C7A—C21A—C26A	−116.4 (5)	C6B—C7B—C21B—C26B	115.9 (5)
C6A—C7A—C21A—C26A	113.3 (5)	C8B—C7B—C21B—C26B	−114.8 (5)
O2A—C7A—C21A—C22A	177.9 (4)	O2B—C7B—C21B—C22B	−178.6 (4)
C8A—C7A—C21A—C22A	62.5 (5)	C6B—C7B—C21B—C22B	−64.2 (6)
C6A—C7A—C21A—C22A	−67.8 (5)	C8B—C7B—C21B—C22B	65.1 (5)
C26A—C21A—C22A—C23A	1.0 (8)	C26B—C21B—C22B—C23B	−1.4 (7)
C7A—C21A—C22A—C23A	−177.9 (4)	C7B—C21B—C22B—C23B	178.7 (4)
C21A—C22A—C23A—C24A	−0.6 (8)	C21B—C22B—C23B—C24B	−0.4 (8)
C22A—C23A—C24A—C25A	−1.0 (9)	C22B—C23B—C24B—C25B	2.2 (8)
C23A—C24A—C25A—C26A	2.2 (10)	C23B—C24B—C25B—C26B	−2.1 (8)
C22A—C21A—C26A—C25A	0.2 (8)	C22B—C21B—C26B—C25B	1.4 (7)
C7A—C21A—C26A—C25A	179.1 (5)	C7B—C21B—C26B—C25B	−178.7 (5)
C24A—C25A—C26A—C21A	−1.8 (10)	C24B—C25B—C26B—C21B	0.3 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16A—H16A···O1A	0.93	2.31	2.678 (5)	103
C16B—H16B···O1B	0.93	2.30	2.667 (6)	103
C17B—H17B···O1A^i	0.93	2.58	3.299 (6)	134
C26A—H26A···O2A	0.93	2.33	2.689 (7)	102
C26B—H26B···O2B	0.93	2.29	2.666 (6)	103

Symmetry code: (i) x, −y+3/2, z+1/2.

(II) 9,10-Dihydro-9,9-dimethoxy-10-hydroxy-10-phenylanthracene

Crystal data

C22H20O3	Dx = 1.283 Mg m^−3
Mr = 332.38	Melting point: 462(1)K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.9181 (10) Å	Cell parameters from 3446 reflections
b = 11.3071 (12) Å	θ = 2.9–28.3°
c = 17.0624 (19) Å	µ = 0.08 mm^−1
β = 90.552 (2)°	T = 293 K
V = 1720.5 (3) Å^3	Slab, colorless
Z = 4	0.36 × 0.26 × 0.20 mm
F(000) = 704

Data collection

Siemens SMART CCD area detector diffractometer	3015 independent reflections
Radiation source: fine-focus sealed tube	2366 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 2.9°
ω scans	h = −10→10
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.970, Tmax = 0.983	l = −13→20
8361 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.042P)^2 + 1.1659P] where P = (Fo^2 + 2Fc^2)/3
3015 reflections	(Δ/σ)max < 0.001
284 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2559 (2)	0.15700 (14)	0.17655 (12)	0.0409 (5)
O2	−0.0249 (2)	0.57475 (14)	0.16372 (11)	0.0471 (5)
O3	−0.0666 (2)	0.46821 (16)	0.26529 (10)	0.0470 (5)
C1	0.0536 (2)	0.27092 (19)	0.11861 (13)	0.0295 (5)
C2	−0.0111 (3)	0.1798 (2)	0.07407 (15)	0.0388 (6)
C3	−0.1604 (3)	0.1820 (3)	0.05309 (16)	0.0449 (7)
C4	−0.2497 (3)	0.2751 (3)	0.07649 (16)	0.0471 (7)
C5	−0.1890 (3)	0.3635 (2)	0.12139 (16)	0.0434 (6)
C6	−0.0378 (2)	0.3630 (2)	0.14343 (13)	0.0318 (5)
C7	0.0174 (3)	0.4633 (2)	0.19507 (14)	0.0349 (6)
C8	0.1839 (3)	0.4590 (2)	0.21295 (13)	0.0319 (5)
C9	0.2448 (3)	0.5495 (2)	0.25923 (15)	0.0420 (6)
C10	0.3938 (3)	0.5512 (2)	0.27823 (17)	0.0481 (7)
C11	0.4870 (3)	0.4622 (2)	0.25141 (16)	0.0438 (7)
C12	0.4285 (3)	0.3726 (2)	0.20671 (15)	0.0378 (6)
C13	0.2764 (2)	0.36874 (19)	0.18682 (13)	0.0292 (5)
C14	0.2215 (2)	0.26524 (18)	0.13683 (13)	0.0297 (5)
C15	0.3067 (2)	0.2617 (2)	0.05913 (14)	0.0325 (5)
C16	0.3528 (3)	0.1553 (3)	0.02712 (18)	0.0500 (7)
C17	0.4212 (4)	0.1526 (3)	−0.0451 (2)	0.0689 (10)
C18	0.4486 (4)	0.2547 (4)	−0.0860 (2)	0.0690 (10)
C19	0.4063 (3)	0.3612 (3)	−0.05422 (17)	0.0577 (8)
C20	0.3353 (3)	0.3650 (2)	0.01763 (16)	0.0425 (6)
C21	0.0440 (4)	0.6043 (3)	0.09164 (17)	0.0603 (8)
H21A	−0.0063	0.6711	0.0687	0.090*
H21B	0.0373	0.5382	0.0565	0.090*
H21C	0.1474	0.6236	0.1009	0.090*
C22	−0.0470 (4)	0.3712 (3)	0.31688 (18)	0.0657 (9)
H22A	−0.1098	0.3814	0.3618	0.099*
H22B	0.0560	0.3671	0.3335	0.099*
H22C	−0.0740	0.2993	0.2903	0.099*
H2	0.051 (3)	0.113 (2)	0.0579 (14)	0.043 (7)*
H3	−0.201 (3)	0.121 (2)	0.0221 (16)	0.056 (8)*
H4	−0.349 (3)	0.280 (2)	0.0624 (16)	0.055 (8)*
H5	−0.249 (3)	0.431 (2)	0.1387 (14)	0.045 (7)*
H9	0.178 (3)	0.611 (2)	0.2769 (14)	0.044 (7)*
H10	0.435 (3)	0.615 (3)	0.3091 (18)	0.069 (9)*
H11	0.587 (3)	0.466 (2)	0.2633 (16)	0.054 (8)*
H12	0.490 (3)	0.308 (2)	0.1877 (14)	0.040 (7)*
H16	0.336 (3)	0.085 (3)	0.0568 (16)	0.057 (9)*
H18	0.491 (4)	0.253 (3)	−0.138 (2)	0.095 (12)*
H19	0.422 (4)	0.434 (3)	−0.082 (2)	0.080 (11)*
H17	0.451 (4)	0.079 (3)	−0.065 (2)	0.088 (11)*
H20	0.303 (3)	0.441 (2)	0.0415 (16)	0.054 (8)*
H1O1	0.192 (4)	0.141 (3)	0.206 (2)	0.077 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0324 (10)	0.0303 (9)	0.0600 (12)	0.0024 (7)	0.0000 (9)	0.0135 (8)
O2	0.0523 (11)	0.0320 (9)	0.0568 (12)	0.0113 (8)	−0.0018 (9)	0.0033 (8)
O3	0.0481 (11)	0.0476 (11)	0.0455 (11)	0.0087 (8)	0.0159 (8)	−0.0057 (9)
C1	0.0283 (12)	0.0279 (12)	0.0324 (12)	−0.0009 (9)	0.0014 (10)	0.0024 (10)
C2	0.0343 (14)	0.0361 (14)	0.0459 (15)	−0.0031 (11)	0.0009 (11)	−0.0029 (12)
C3	0.0366 (15)	0.0528 (17)	0.0453 (16)	−0.0140 (13)	−0.0026 (12)	−0.0017 (13)
C4	0.0253 (14)	0.0657 (19)	0.0503 (17)	−0.0007 (13)	−0.0040 (12)	0.0070 (14)
C5	0.0299 (13)	0.0490 (16)	0.0512 (17)	0.0065 (12)	0.0012 (12)	0.0021 (13)
C6	0.0279 (12)	0.0338 (13)	0.0338 (13)	0.0015 (10)	0.0013 (10)	0.0062 (10)
C7	0.0347 (13)	0.0314 (13)	0.0386 (14)	0.0071 (10)	0.0048 (11)	−0.0006 (11)
C8	0.0351 (13)	0.0301 (12)	0.0305 (12)	0.0008 (10)	0.0009 (10)	0.0013 (10)
C9	0.0493 (17)	0.0343 (14)	0.0423 (15)	0.0020 (12)	−0.0007 (12)	−0.0068 (12)
C10	0.0544 (18)	0.0423 (16)	0.0475 (16)	−0.0101 (13)	−0.0094 (13)	−0.0079 (13)
C11	0.0341 (15)	0.0528 (17)	0.0443 (16)	−0.0095 (13)	−0.0086 (12)	−0.0011 (13)
C12	0.0312 (14)	0.0391 (14)	0.0431 (15)	−0.0007 (11)	−0.0006 (11)	−0.0032 (12)
C13	0.0275 (12)	0.0304 (12)	0.0296 (12)	−0.0011 (9)	−0.0006 (9)	0.0053 (10)
C14	0.0269 (12)	0.0238 (11)	0.0384 (13)	0.0017 (9)	0.0018 (10)	0.0021 (10)
C15	0.0228 (12)	0.0357 (13)	0.0390 (14)	0.0003 (10)	−0.0019 (10)	−0.0072 (11)
C16	0.0474 (16)	0.0408 (16)	0.062 (2)	−0.0024 (13)	0.0126 (14)	−0.0147 (14)
C17	0.065 (2)	0.070 (2)	0.071 (2)	0.0036 (18)	0.0174 (18)	−0.032 (2)
C18	0.066 (2)	0.100 (3)	0.0410 (18)	0.008 (2)	0.0126 (16)	−0.0116 (19)
C19	0.0549 (19)	0.075 (2)	0.0437 (17)	0.0099 (16)	0.0069 (14)	0.0144 (16)
C20	0.0395 (15)	0.0437 (16)	0.0442 (16)	0.0103 (12)	0.0045 (12)	0.0061 (12)
C21	0.091 (2)	0.0420 (16)	0.0473 (17)	−0.0006 (15)	−0.0111 (16)	0.0097 (14)
C22	0.085 (2)	0.063 (2)	0.0502 (18)	−0.0030 (17)	0.0230 (17)	0.0074 (16)

Geometric parameters (Å, º)

O1—C14	1.431 (3)	C10—H10	0.96 (3)
O1—H1O1	0.79 (3)	C11—C12	1.368 (3)
O2—C7	1.419 (3)	C11—H11	0.92 (3)
O2—C21	1.420 (3)	C12—C13	1.396 (3)
O3—C22	1.416 (3)	C12—H12	0.97 (2)
O3—C7	1.420 (3)	C13—C14	1.526 (3)
C1—C6	1.391 (3)	C14—C15	1.535 (3)
C1—C2	1.402 (3)	C15—C16	1.386 (3)
C1—C14	1.528 (3)	C15—C20	1.391 (3)
C2—C3	1.375 (4)	C16—C17	1.380 (4)
C2—H2	0.97 (3)	C16—H16	0.96 (3)
C3—C4	1.382 (4)	C17—C18	1.373 (5)
C3—H3	0.94 (3)	C17—H17	0.94 (4)
C4—C5	1.367 (4)	C18—C19	1.374 (5)
C4—H4	0.92 (3)	C18—H18	0.96 (4)
C5—C6	1.396 (3)	C19—C20	1.386 (4)
C5—H5	0.97 (3)	C19—H19	0.96 (3)
C6—C7	1.515 (3)	C20—H20	1.00 (3)
C7—C8	1.513 (3)	C21—H21A	0.9600
C8—C13	1.389 (3)	C21—H21B	0.9600
C8—C9	1.399 (3)	C21—H21C	0.9600
C9—C10	1.365 (4)	C22—H22A	0.9600
C9—H9	0.97 (3)	C22—H22B	0.9600
C10—C11	1.386 (4)	C22—H22C	0.9600
C14—O1—H1O1	110 (3)	C13—C12—H12	116.5 (14)
C7—O2—C21	114.82 (19)	C8—C13—C12	118.6 (2)
C22—O3—C7	115.54 (19)	C8—C13—C14	123.70 (19)
C6—C1—C2	118.4 (2)	C12—C13—C14	117.7 (2)
C6—C1—C14	123.1 (2)	O1—C14—C13	108.98 (18)
C2—C1—C14	118.5 (2)	O1—C14—C1	109.71 (17)
C3—C2—C1	121.4 (2)	C13—C14—C1	112.95 (17)
C3—C2—H2	119.3 (15)	O1—C14—C15	106.36 (18)
C1—C2—H2	119.3 (15)	C13—C14—C15	110.13 (17)
C2—C3—C4	119.9 (3)	C1—C14—C15	108.51 (18)
C2—C3—H3	120.0 (17)	C16—C15—C20	118.2 (2)
C4—C3—H3	120.2 (17)	C16—C15—C14	120.9 (2)
C5—C4—C3	119.5 (3)	C20—C15—C14	120.9 (2)
C5—C4—H4	118.7 (17)	C17—C16—C15	120.4 (3)
C3—C4—H4	121.8 (17)	C17—C16—H16	121.7 (17)
C4—C5—C6	121.6 (3)	C15—C16—H16	117.9 (17)
C4—C5—H5	121.6 (15)	C18—C17—C16	121.2 (3)
C6—C5—H5	116.7 (15)	C18—C17—H17	120 (2)
C1—C6—C5	119.2 (2)	C16—C17—H17	118 (2)
C1—C6—C7	123.3 (2)	C17—C18—C19	119.0 (3)
C5—C6—C7	117.5 (2)	C17—C18—H18	122 (2)
O2—C7—O3	98.19 (17)	C19—C18—H18	119 (2)
O2—C7—C8	111.16 (19)	C18—C19—C20	120.4 (3)
O3—C7—C8	110.82 (19)	C18—C19—H19	121 (2)
O2—C7—C6	111.20 (19)	C20—C19—H19	119 (2)
O3—C7—C6	110.44 (19)	C19—C20—C15	120.8 (3)
C8—C7—C6	113.96 (18)	C19—C20—H20	121.6 (16)
C13—C8—C9	119.3 (2)	C15—C20—H20	117.7 (15)
C13—C8—C7	122.9 (2)	O2—C21—H21A	109.5
C9—C8—C7	117.7 (2)	O2—C21—H21B	109.5
C10—C9—C8	121.1 (2)	H21A—C21—H21B	109.5
C10—C9—H9	121.2 (15)	O2—C21—H21C	109.5
C8—C9—H9	117.7 (15)	H21A—C21—H21C	109.5
C9—C10—C11	119.8 (3)	H21B—C21—H21C	109.5
C9—C10—H10	120.4 (18)	O3—C22—H22A	109.5
C11—C10—H10	119.8 (18)	O3—C22—H22B	109.5
C12—C11—C10	119.7 (3)	H22A—C22—H22B	109.5
C12—C11—H11	121.8 (17)	O3—C22—H22C	109.5
C10—C11—H11	118.5 (17)	H22A—C22—H22C	109.5
C11—C12—C13	121.5 (2)	H22B—C22—H22C	109.5
C11—C12—H12	121.9 (14)
C6—C1—C2—C3	1.9 (4)	C10—C11—C12—C13	0.4 (4)
C14—C1—C2—C3	−177.5 (2)	C9—C8—C13—C12	−1.1 (3)
C1—C2—C3—C4	−0.4 (4)	C7—C8—C13—C12	−179.7 (2)
C2—C3—C4—C5	−1.0 (4)	C9—C8—C13—C14	179.3 (2)
C3—C4—C5—C6	0.9 (4)	C7—C8—C13—C14	0.7 (3)
C2—C1—C6—C5	−1.9 (3)	C11—C12—C13—C8	0.5 (4)
C14—C1—C6—C5	177.4 (2)	C11—C12—C13—C14	−179.9 (2)
C2—C1—C6—C7	176.9 (2)	C8—C13—C14—O1	−122.4 (2)
C14—C1—C6—C7	−3.8 (3)	C12—C13—C14—O1	58.1 (3)
C4—C5—C6—C1	0.5 (4)	C8—C13—C14—C1	−0.2 (3)
C4—C5—C6—C7	−178.4 (2)	C12—C13—C14—C1	−179.7 (2)
C21—O2—C7—O3	177.9 (2)	C8—C13—C14—C15	121.3 (2)
C21—O2—C7—C8	61.7 (3)	C12—C13—C14—C15	−58.3 (3)
C21—O2—C7—C6	−66.4 (3)	C6—C1—C14—O1	123.5 (2)
C22—O3—C7—O2	−176.7 (2)	C2—C1—C14—O1	−57.2 (3)
C22—O3—C7—C8	−60.3 (3)	C6—C1—C14—C13	1.7 (3)
C22—O3—C7—C6	66.9 (3)	C2—C1—C14—C13	−179.0 (2)
C1—C6—C7—O2	130.5 (2)	C6—C1—C14—C15	−120.7 (2)
C5—C6—C7—O2	−50.7 (3)	C2—C1—C14—C15	58.6 (3)
C1—C6—C7—O3	−121.6 (2)	O1—C14—C15—C16	21.8 (3)
C5—C6—C7—O3	57.3 (3)	C13—C14—C15—C16	139.8 (2)
C1—C6—C7—C8	3.9 (3)	C1—C14—C15—C16	−96.2 (3)
C5—C6—C7—C8	−177.2 (2)	O1—C14—C15—C20	−160.3 (2)
O2—C7—C8—C13	−129.0 (2)	C13—C14—C15—C20	−42.4 (3)
O3—C7—C8—C13	122.9 (2)	C1—C14—C15—C20	81.7 (3)
C6—C7—C8—C13	−2.4 (3)	C20—C15—C16—C17	−1.9 (4)
O2—C7—C8—C9	52.3 (3)	C14—C15—C16—C17	176.1 (3)
O3—C7—C8—C9	−55.7 (3)	C15—C16—C17—C18	1.6 (5)
C6—C7—C8—C9	179.0 (2)	C16—C17—C18—C19	−0.2 (5)
C13—C8—C9—C10	0.9 (4)	C17—C18—C19—C20	−0.9 (5)
C7—C8—C9—C10	179.6 (2)	C18—C19—C20—C15	0.6 (4)
C8—C9—C10—C11	0.0 (4)	C16—C15—C20—C19	0.8 (4)
C9—C10—C11—C12	−0.6 (4)	C14—C15—C20—C19	−177.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1	0.96 (3)	2.32 (3)	2.700 (4)	103 (2)
O1—H1O1···O3^i	0.78 (3)	2.31 (3)	2.902 (2)	133 (3)

Symmetry code: (i) −x, y−1/2, −z+1/2.