Brasilixanthone.

THE TITLE XANTHONE [SYSTEMATIC NAME: 5,13-dihy-droxy-3,3,10,10-tetra-methyl-3H-dipyrano[3,2-a:2',3'-i]xanthen-14(10H)-one], C(23)H(20)O(6), was isolated from the roots of Cratoxylum formosum ssp. pruniflorum. There are two mol-ecules (A and B) in the asymmetric unit, which show chemical but not crystallographic inversion symmetry. The xanthone skeleton in both mol-ecules is approximately planar, with an r.m.s. deviation of 0.0326 (9) Å for mol-ecule A and 0.0355 (9) Å for mol-ecule B from the plane through the 14 non-H atoms. The pyran rings in both mol-ecules adopt sofa conformations. Intra-molecular O-H⋯O hydrogen bonds generate S(5) and S(6) ring motifs. Viewed onto the bc plane, the crystal structure resembles a herringbone pattern. Stacks of mol-ecules are stabilized by π-π inter-actions with centroid-centroid distances of 3.600 (5) Å. The crystal structure is further stabilized by weak C-H⋯O and C-H⋯π inter-actions.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶) and for ring conformations, see: Cremer & Pople (1975 ▶). For background to xanthones and their biological activities, see: Boonnak et al. (2006 ▶, 2007 ▶, 2009 ▶); Hay et al. (2008 ▶); Mahabusarakum et al. (1983 ▶); Marques et al. (2000 ▶); Molinar-Toribio et al. (2006 ▶); Phongpaichit et al. (1994 ▶); Yu et al. (2007 ▶). For a related structure, see: Fun et al. (2006 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C23H20O6

M = 392.39

Monoclinic,

a = 7.5842 (3) Å

b = 12.2937 (4) Å

c = 19.6023 (6) Å

β = 96.827 (2)°

V = 1814.72 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.37 × 0.13 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.963, T max = 0.993

33718 measured reflections

3554 independent reflections

2954 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.103

wR(F 2) = 0.270

S = 1.04

3554 reflections

453 parameters

2 restraints

H-atom parameters constrained

Δρmax = 1.21 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027285/bt5295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027285/bt5295Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H20O6	F(000) = 824
Mr = 392.39	Dx = 1.436 Mg m−3
Monoclinic, Pc	Melting point = 478–480 K
Hall symbol: P -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 7.5842 (3) Å	Cell parameters from 3554 reflections
b = 12.2937 (4) Å	θ = 2.0–26.0°
c = 19.6023 (6) Å	µ = 0.10 mm−1
β = 96.827 (2)°	T = 100 K
V = 1814.72 (11) Å3	Needle, yellow
Z = 4	0.37 × 0.13 × 0.07 mm

Bruker APEXII CCD area-detector diffractometer	3554 independent reflections
Radiation source: sealed tube	2954 reflections with I > 2σ(I)
graphite	Rint = 0.077
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.963, Tmax = 0.993	k = −15→15
33718 measured reflections	l = −24→23

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)] = 0.103	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.270	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1648P)2 + 5.5181P] where P = (Fo2 + 2Fc2)/3
3554 reflections	(Δ/σ)max = 0.001
453 parameters	Δρmax = 1.21 e Å−3
2 restraints	Δρmin = −0.39 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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

Refinement. 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
O1A	0.2594 (8)	0.6225 (5)	0.5423 (3)	0.0284 (14)
O2A	0.7864 (8)	0.5793 (5)	0.6095 (4)	0.0300 (15)
O3A	0.7794 (8)	0.7513 (5)	0.6837 (3)	0.0299 (15)
H3AA	0.8227	0.6975	0.6674	0.045*
O4A	0.5559 (8)	0.2608 (5)	0.4390 (3)	0.0254 (13)
O5A	0.2102 (8)	0.3007 (5)	0.4131 (3)	0.0289 (14)
H5AA	0.2715	0.2500	0.4024	0.043*
O6A	0.2246 (8)	0.9394 (5)	0.6739 (3)	0.0256 (14)
C1A	0.6044 (13)	0.4207 (7)	0.5107 (5)	0.0251 (19)
C2A	0.4941 (11)	0.3517 (7)	0.4674 (4)	0.0219 (6)
C3A	0.3142 (12)	0.3725 (7)	0.4539 (4)	0.0252 (18)
C4A	0.2407 (11)	0.4679 (7)	0.4795 (4)	0.0219 (6)
H4AA	0.1211	0.4849	0.4685	0.026*
C5A	0.2460 (11)	0.7814 (7)	0.6065 (5)	0.0254 (18)
H5AB	0.1273	0.7895	0.5889	0.031*
C6A	0.3293 (13)	0.8539 (7)	0.6537 (4)	0.0275 (14)
C7A	0.5028 (12)	0.8473 (7)	0.6790 (5)	0.029 (2)
C8A	0.6086 (12)	0.7602 (8)	0.6578 (5)	0.030 (2)
C9A	0.6311 (12)	0.5885 (8)	0.5873 (4)	0.028 (2)
C10A	0.5222 (12)	0.5135 (7)	0.5380 (5)	0.028 (2)
C11A	0.3485 (13)	0.5325 (7)	0.5197 (5)	0.0271 (19)
C12A	0.3513 (13)	0.6930 (8)	0.5859 (4)	0.0275 (14)
C13A	0.5217 (13)	0.6810 (8)	0.6099 (5)	0.029 (2)
C14A	0.7423 (11)	0.2633 (7)	0.4260 (5)	0.0219 (6)
C15A	0.8475 (12)	0.3104 (7)	0.4909 (5)	0.0244 (13)
H15A	0.9617	0.2847	0.5042	0.029*
C16A	0.7838 (12)	0.3844 (7)	0.5280 (4)	0.0244 (13)
H16A	0.8539	0.4139	0.5656	0.029*
C17A	0.7541 (11)	0.3372 (7)	0.3641 (4)	0.0235 (17)
H17A	0.6762	0.3105	0.3256	0.035*
H17B	0.8739	0.3378	0.3529	0.035*
H17C	0.7197	0.4097	0.3750	0.035*
C18A	0.7952 (13)	0.1488 (7)	0.4115 (5)	0.031 (2)
H18A	0.7115	0.1184	0.3760	0.047*
H18B	0.7965	0.1059	0.4525	0.047*
H18C	0.9115	0.1487	0.3968	0.047*
C19A	0.2789 (11)	0.9818 (7)	0.7425 (4)	0.0219 (6)
C20A	0.4757 (11)	0.9990 (8)	0.7499 (4)	0.0219 (6)
H20A	0.5231	1.0607	0.7725	0.026*
C21A	0.5832 (12)	0.9296 (7)	0.7253 (5)	0.0269 (19)
H21A	0.7055	0.9332	0.7372	0.032*
C22A	0.2221 (11)	0.9032 (7)	0.7950 (4)	0.0219 (6)
H22A	0.2928	0.8383	0.7954	0.033*
H22B	0.0992	0.8849	0.7832	0.033*
H22C	0.2384	0.9363	0.8396	0.033*
C23A	0.1815 (13)	1.0908 (8)	0.7424 (5)	0.030 (2)
H23A	0.2025	1.1318	0.7025	0.046*
H23B	0.2245	1.1310	0.7830	0.046*
H23C	0.0564	1.0781	0.7417	0.046*
O1B	0.7714 (6)	0.1279 (5)	0.6348 (3)	0.0170 (11)
O2B	0.2460 (7)	0.1655 (5)	0.5601 (3)	0.0224 (13)
O3B	0.2679 (7)	−0.0013 (5)	0.4835 (3)	0.0243 (14)
H3BA	0.2190	0.0505	0.4997	0.036*
O4B	0.4578 (7)	0.4885 (5)	0.7314 (3)	0.0234 (13)
O5B	0.7974 (7)	0.4482 (5)	0.7649 (3)	0.0265 (14)
H5BA	0.7316	0.4976	0.7742	0.032*
O6B	0.8254 (8)	−0.1813 (5)	0.5014 (3)	0.0230 (13)
C1B	0.4180 (11)	0.3280 (7)	0.6589 (4)	0.0219 (6)
C2B	0.5194 (11)	0.3932 (7)	0.7039 (4)	0.0219 (6)
C3B	0.7035 (11)	0.3754 (7)	0.7233 (4)	0.0195 (16)
C4B	0.7810 (10)	0.2841 (7)	0.6989 (4)	0.0186 (16)
H4BA	0.9004	0.2689	0.7120	0.022*
C5B	0.7971 (10)	−0.0268 (6)	0.5681 (4)	0.0168 (9)
H5BB	0.9150	−0.0335	0.5871	0.020*
C6B	0.7222 (10)	−0.1000 (7)	0.5196 (4)	0.0168 (9)
C7B	0.5435 (10)	−0.0911 (6)	0.4902 (4)	0.0177 (11)
C8B	0.4416 (10)	−0.0059 (6)	0.5117 (4)	0.0139 (15)
C9B	0.4054 (10)	0.1592 (6)	0.5834 (4)	0.0155 (15)
C10B	0.4968 (9)	0.2335 (7)	0.6322 (4)	0.0158 (16)
C11B	0.6794 (10)	0.2163 (7)	0.6551 (4)	0.0168 (9)
C12B	0.6909 (11)	0.0571 (6)	0.5876 (4)	0.0177 (11)
C13B	0.5122 (10)	0.0696 (7)	0.5609 (4)	0.0161 (16)
C14B	0.2689 (10)	0.4816 (6)	0.7418 (4)	0.0145 (15)
C15B	0.1709 (11)	0.4396 (7)	0.6785 (4)	0.0188 (16)
H15B	0.0594	0.4685	0.6640	0.023*
C16B	0.2338 (10)	0.3616 (7)	0.6407 (4)	0.0201 (17)
H16B	0.1629	0.3299	0.6041	0.024*
C17B	0.2476 (11)	0.4105 (7)	0.8039 (4)	0.0213 (13)
H17D	0.3047	0.3417	0.7990	0.032*
H17E	0.1236	0.3989	0.8069	0.032*
H17F	0.3009	0.4459	0.8448	0.032*
C18B	0.2195 (11)	0.6005 (7)	0.7543 (4)	0.0213 (13)
H18D	0.2315	0.6426	0.7139	0.032*
H18E	0.2972	0.6291	0.7923	0.032*
H18F	0.0990	0.6040	0.7645	0.032*
C19B	0.7833 (11)	−0.2314 (7)	0.4314 (4)	0.0216 (18)
C20B	0.5868 (11)	−0.2446 (7)	0.4176 (5)	0.0244 (18)
H20B	0.5415	−0.3022	0.3901	0.029*
C21B	0.4738 (10)	−0.1771 (7)	0.4431 (5)	0.0240 (18)
H21B	0.3520	−0.1846	0.4311	0.029*
C22B	0.8534 (13)	−0.1520 (8)	0.3810 (5)	0.034 (2)
H22D	0.9794	−0.1439	0.3921	0.050*
H22E	0.7969	−0.0826	0.3842	0.050*
H22F	0.8279	−0.1797	0.3351	0.050*
C23B	0.8837 (12)	−0.3365 (7)	0.4352 (5)	0.028 (2)
H23D	1.0078	−0.3223	0.4477	0.042*
H23E	0.8670	−0.3718	0.3912	0.042*
H23F	0.8408	−0.3828	0.4690	0.042*

	U11	U22	U33	U12	U13	U23
O1A	0.024 (3)	0.022 (3)	0.040 (4)	0.005 (2)	0.004 (3)	0.004 (3)
O2A	0.017 (3)	0.029 (3)	0.042 (4)	0.002 (3)	−0.002 (3)	0.007 (3)
O3A	0.018 (3)	0.037 (4)	0.034 (4)	0.013 (3)	0.001 (3)	−0.001 (3)
O4A	0.021 (3)	0.018 (3)	0.038 (4)	−0.006 (2)	0.005 (3)	0.002 (3)
O5A	0.023 (3)	0.025 (3)	0.037 (4)	−0.006 (2)	−0.002 (3)	−0.007 (3)
O6A	0.029 (3)	0.021 (3)	0.026 (3)	0.004 (3)	0.002 (3)	−0.002 (3)
C1A	0.043 (5)	0.012 (4)	0.023 (4)	−0.009 (4)	0.017 (4)	−0.003 (3)
C2A	0.0241 (14)	0.0209 (14)	0.0229 (14)	0.0040 (11)	0.0117 (11)	0.0043 (11)
C3A	0.035 (5)	0.020 (4)	0.021 (4)	−0.005 (3)	0.006 (4)	0.003 (3)
C4A	0.0241 (14)	0.0209 (14)	0.0229 (14)	0.0040 (11)	0.0117 (11)	0.0043 (11)
C5A	0.015 (4)	0.027 (4)	0.035 (5)	0.004 (3)	0.006 (3)	−0.002 (4)
C6A	0.046 (4)	0.025 (3)	0.013 (3)	−0.013 (3)	0.008 (3)	0.001 (2)
C7A	0.028 (5)	0.024 (4)	0.039 (5)	0.010 (4)	0.023 (4)	0.017 (4)
C8A	0.026 (4)	0.034 (5)	0.029 (5)	−0.018 (4)	0.004 (4)	0.002 (4)
C9A	0.028 (5)	0.035 (5)	0.019 (4)	−0.022 (4)	0.003 (4)	−0.001 (4)
C10A	0.035 (5)	0.017 (4)	0.036 (5)	0.008 (4)	0.027 (4)	0.015 (4)
C11A	0.037 (5)	0.023 (4)	0.023 (4)	−0.007 (4)	0.013 (4)	0.013 (3)
C12A	0.046 (4)	0.025 (3)	0.013 (3)	−0.013 (3)	0.008 (3)	0.001 (2)
C13A	0.033 (5)	0.023 (5)	0.032 (5)	0.003 (4)	0.011 (4)	0.005 (4)
C14A	0.0241 (14)	0.0209 (14)	0.0229 (14)	0.0040 (11)	0.0117 (11)	0.0043 (11)
C15A	0.034 (3)	0.019 (3)	0.021 (3)	−0.012 (2)	0.005 (2)	−0.001 (2)
C16A	0.034 (3)	0.019 (3)	0.021 (3)	−0.012 (2)	0.005 (2)	−0.001 (2)
C17A	0.021 (4)	0.029 (4)	0.021 (4)	−0.003 (3)	0.004 (3)	−0.002 (3)
C18A	0.043 (5)	0.022 (4)	0.030 (5)	0.010 (4)	0.011 (4)	−0.003 (4)
C19A	0.0241 (14)	0.0209 (14)	0.0229 (14)	0.0040 (11)	0.0117 (11)	0.0043 (11)
C20A	0.0241 (14)	0.0209 (14)	0.0229 (14)	0.0040 (11)	0.0117 (11)	0.0043 (11)
C21A	0.031 (5)	0.027 (5)	0.023 (4)	0.013 (4)	0.006 (3)	0.012 (4)
C22A	0.0241 (14)	0.0209 (14)	0.0229 (14)	0.0040 (11)	0.0117 (11)	0.0043 (11)
C23A	0.035 (5)	0.030 (5)	0.030 (5)	0.010 (4)	0.021 (4)	0.001 (4)
O1B	0.011 (2)	0.028 (3)	0.011 (3)	−0.001 (2)	0.001 (2)	−0.004 (2)
O2B	0.017 (3)	0.035 (3)	0.016 (3)	0.004 (2)	0.003 (2)	−0.003 (2)
O3B	0.015 (3)	0.033 (3)	0.023 (3)	0.005 (2)	−0.005 (2)	−0.007 (3)
O4B	0.017 (3)	0.018 (3)	0.036 (3)	0.007 (2)	0.010 (2)	−0.009 (3)
O5B	0.018 (3)	0.024 (3)	0.039 (4)	0.001 (2)	0.006 (3)	−0.009 (3)
O6B	0.028 (3)	0.017 (3)	0.023 (3)	0.004 (2)	−0.005 (2)	−0.010 (2)
C1B	0.0241 (14)	0.0209 (14)	0.0229 (14)	0.0040 (11)	0.0117 (11)	0.0043 (11)
C2B	0.0241 (14)	0.0209 (14)	0.0229 (14)	0.0040 (11)	0.0117 (11)	0.0043 (11)
C3B	0.023 (4)	0.022 (4)	0.015 (4)	0.000 (3)	0.007 (3)	−0.007 (3)
C4B	0.010 (3)	0.030 (4)	0.016 (4)	0.001 (3)	0.004 (3)	0.007 (3)
C5B	0.016 (2)	0.018 (2)	0.017 (2)	0.0005 (17)	0.0055 (17)	−0.0026 (18)
C6B	0.016 (2)	0.018 (2)	0.017 (2)	0.0005 (17)	0.0055 (17)	−0.0026 (18)
C7B	0.025 (3)	0.012 (2)	0.017 (3)	0.003 (2)	0.006 (2)	−0.006 (2)
C8B	0.018 (4)	0.009 (3)	0.016 (3)	0.000 (3)	0.008 (3)	0.004 (3)
C9B	0.018 (4)	0.013 (4)	0.016 (4)	0.005 (3)	0.004 (3)	0.005 (3)
C10B	0.012 (3)	0.026 (4)	0.009 (3)	0.000 (3)	0.000 (3)	−0.004 (3)
C11B	0.016 (2)	0.018 (2)	0.017 (2)	0.0005 (17)	0.0055 (17)	−0.0026 (18)
C12B	0.025 (3)	0.012 (2)	0.017 (3)	0.003 (2)	0.006 (2)	−0.006 (2)
C13B	0.016 (4)	0.026 (4)	0.006 (3)	0.001 (3)	−0.001 (3)	0.003 (3)
C14B	0.013 (3)	0.013 (4)	0.019 (4)	0.006 (3)	0.007 (3)	−0.001 (3)
C15B	0.024 (4)	0.015 (4)	0.016 (4)	0.008 (3)	0.000 (3)	−0.001 (3)
C16B	0.020 (4)	0.021 (4)	0.020 (4)	0.001 (3)	0.010 (3)	0.003 (3)
C17B	0.024 (3)	0.019 (3)	0.023 (3)	0.012 (2)	0.012 (2)	0.004 (2)
C18B	0.024 (3)	0.019 (3)	0.023 (3)	0.012 (2)	0.012 (2)	0.004 (2)
C19B	0.028 (4)	0.028 (4)	0.009 (3)	0.007 (3)	0.000 (3)	−0.008 (3)
C20B	0.023 (4)	0.016 (4)	0.031 (5)	0.002 (3)	−0.007 (3)	−0.006 (3)
C21B	0.009 (3)	0.031 (5)	0.029 (4)	−0.008 (3)	−0.007 (3)	−0.007 (4)
C22B	0.033 (5)	0.040 (5)	0.030 (5)	0.015 (4)	0.016 (4)	0.003 (4)
C23B	0.029 (4)	0.024 (4)	0.031 (5)	0.016 (4)	0.003 (4)	−0.006 (4)

O1A—C12A	1.351 (11)	O1B—C12B	1.361 (9)
O1A—C11A	1.395 (11)	O1B—C11B	1.375 (9)
O2A—C9A	1.211 (11)	O2B—C9B	1.242 (9)
O3A—C8A	1.338 (11)	O3B—C8B	1.368 (9)
O3A—H3AA	0.8200	O3B—H3BA	0.8200
O4A—C2A	1.356 (10)	O4B—C2B	1.393 (10)
O4A—C14A	1.467 (10)	O4B—C14B	1.473 (9)
O5A—C3A	1.376 (10)	O5B—C3B	1.355 (10)
O5A—H5AA	0.8200	O5B—H5BA	0.8200
O6A—C6A	1.402 (11)	O6B—C6B	1.343 (9)
O6A—C19A	1.455 (11)	O6B—C19B	1.503 (9)
C1A—C2A	1.405 (13)	C1B—C2B	1.361 (13)
C1A—C16A	1.433 (14)	C1B—C10B	1.434 (11)
C1A—C10A	1.434 (12)	C1B—C16B	1.460 (11)
C2A—C3A	1.382 (12)	C2B—C3B	1.420 (12)
C3A—C4A	1.416 (12)	C3B—C4B	1.379 (11)
C4A—C11A	1.330 (13)	C4B—C11B	1.367 (12)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.382 (12)	C5B—C6B	1.382 (11)
C5A—C12A	1.434 (12)	C5B—C12B	1.390 (10)
C5A—H5AB	0.9300	C5B—H5BB	0.9300
C6A—C7A	1.352 (14)	C6B—C7B	1.412 (11)
C7A—C8A	1.429 (13)	C7B—C8B	1.397 (10)
C7A—C21A	1.446 (14)	C7B—C21B	1.461 (11)
C8A—C13A	1.454 (13)	C8B—C13B	1.398 (11)
C9A—C13A	1.505 (13)	C9B—C10B	1.439 (11)
C9A—C10A	1.508 (13)	C9B—C13B	1.466 (10)
C10A—C11A	1.344 (14)	C10B—C11B	1.420 (10)
C12A—C13A	1.331 (14)	C12B—C13B	1.402 (11)
C14A—C18A	1.501 (12)	C14B—C15B	1.463 (11)
C14A—C17A	1.527 (12)	C14B—C17B	1.522 (11)
C14A—C15A	1.532 (12)	C14B—C18B	1.535 (10)
C15A—C16A	1.293 (13)	C15B—C16B	1.334 (11)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—H17A	0.9600	C17B—H17D	0.9600
C17A—H17B	0.9600	C17B—H17E	0.9600
C17A—H17C	0.9600	C17B—H17F	0.9600
C18A—H18A	0.9600	C18B—H18D	0.9600
C18A—H18B	0.9600	C18B—H18E	0.9600
C18A—H18C	0.9600	C18B—H18F	0.9600
C19A—C20A	1.498 (11)	C19B—C20B	1.491 (11)
C19A—C22A	1.511 (11)	C19B—C23B	1.497 (11)
C19A—C23A	1.530 (12)	C19B—C22B	1.528 (13)
C20A—C21A	1.309 (12)	C20B—C21B	1.333 (12)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—H21A	0.9300	C21B—H21B	0.9300
C22A—H22A	0.9600	C22B—H22D	0.9600
C22A—H22B	0.9600	C22B—H22E	0.9600
C22A—H22C	0.9600	C22B—H22F	0.9600
C23A—H23A	0.9600	C23B—H23D	0.9600
C23A—H23B	0.9600	C23B—H23E	0.9600
C23A—H23C	0.9600	C23B—H23F	0.9600
C12A—O1A—C11A	118.5 (7)	C12B—O1B—C11B	120.0 (6)
C8A—O3A—H3AA	109.5	C8B—O3B—H3BA	109.5
C2A—O4A—C14A	116.2 (6)	C2B—O4B—C14B	112.4 (6)
C3A—O5A—H5AA	109.5	C3B—O5B—H5BA	109.5
C6A—O6A—C19A	115.0 (7)	C6B—O6B—C19B	118.6 (6)
C2A—C1A—C16A	115.8 (8)	C2B—C1B—C10B	119.1 (8)
C2A—C1A—C10A	116.9 (9)	C2B—C1B—C16B	116.3 (8)
C16A—C1A—C10A	127.0 (9)	C10B—C1B—C16B	124.6 (8)
O4A—C2A—C3A	117.1 (8)	C1B—C2B—O4B	123.8 (8)
O4A—C2A—C1A	122.4 (8)	C1B—C2B—C3B	123.0 (8)
C3A—C2A—C1A	120.5 (8)	O4B—C2B—C3B	113.0 (7)
O5A—C3A—C2A	118.5 (8)	O5B—C3B—C4B	122.1 (7)
O5A—C3A—C4A	121.0 (8)	O5B—C3B—C2B	119.2 (7)
C2A—C3A—C4A	120.5 (8)	C4B—C3B—C2B	118.6 (8)
C11A—C4A—C3A	117.7 (8)	C11B—C4B—C3B	118.9 (7)
C11A—C4A—H4AA	121.2	C11B—C4B—H4BA	120.6
C3A—C4A—H4AA	121.2	C3B—C4B—H4BA	120.6
C6A—C5A—C12A	116.8 (8)	C6B—C5B—C12B	117.9 (7)
C6A—C5A—H5AB	121.6	C6B—C5B—H5BB	121.1
C12A—C5A—H5AB	121.6	C12B—C5B—H5BB	121.1
C7A—C6A—C5A	123.6 (9)	O6B—C6B—C5B	117.5 (7)
C7A—C6A—O6A	120.0 (8)	O6B—C6B—C7B	120.7 (7)
C5A—C6A—O6A	116.3 (8)	C5B—C6B—C7B	121.8 (7)
C6A—C7A—C8A	119.6 (9)	C8B—C7B—C6B	118.3 (7)
C6A—C7A—C21A	120.5 (8)	C8B—C7B—C21B	124.2 (7)
C8A—C7A—C21A	119.9 (8)	C6B—C7B—C21B	117.3 (7)
O3A—C8A—C7A	120.2 (8)	O3B—C8B—C7B	116.7 (7)
O3A—C8A—C13A	122.2 (9)	O3B—C8B—C13B	121.5 (6)
C7A—C8A—C13A	117.5 (9)	C7B—C8B—C13B	121.7 (7)
O2A—C9A—C13A	120.7 (8)	O2B—C9B—C10B	125.2 (7)
O2A—C9A—C10A	127.5 (9)	O2B—C9B—C13B	118.9 (7)
C13A—C9A—C10A	111.8 (8)	C10B—C9B—C13B	115.9 (7)
C11A—C10A—C1A	119.7 (10)	C11B—C10B—C1B	116.0 (7)
C11A—C10A—C9A	120.6 (8)	C11B—C10B—C9B	119.4 (7)
C1A—C10A—C9A	119.7 (8)	C1B—C10B—C9B	124.6 (7)
C4A—C11A—C10A	124.6 (9)	C4B—C11B—O1B	113.3 (7)
C4A—C11A—O1A	112.0 (8)	C4B—C11B—C10B	124.3 (7)
C10A—C11A—O1A	123.3 (9)	O1B—C11B—C10B	122.4 (7)
C13A—C12A—O1A	124.0 (9)	O1B—C12B—C5B	115.7 (7)
C13A—C12A—C5A	122.3 (8)	O1B—C12B—C13B	121.2 (7)
O1A—C12A—C5A	113.7 (8)	C5B—C12B—C13B	123.0 (7)
C12A—C13A—C8A	120.0 (9)	C8B—C13B—C12B	117.3 (7)
C12A—C13A—C9A	121.7 (9)	C8B—C13B—C9B	121.7 (7)
C8A—C13A—C9A	118.2 (8)	C12B—C13B—C9B	121.0 (7)
O4A—C14A—C18A	107.3 (7)	C15B—C14B—O4B	107.9 (6)
O4A—C14A—C17A	107.4 (7)	C15B—C14B—C17B	112.5 (7)
C18A—C14A—C17A	111.4 (7)	O4B—C14B—C17B	110.0 (6)
O4A—C14A—C15A	106.3 (7)	C15B—C14B—C18B	111.2 (7)
C18A—C14A—C15A	112.8 (8)	O4B—C14B—C18B	103.1 (6)
C17A—C14A—C15A	111.2 (7)	C17B—C14B—C18B	111.6 (6)
C16A—C15A—C14A	122.7 (9)	C16B—C15B—C14B	123.1 (7)
C16A—C15A—H15A	118.7	C16B—C15B—H15B	118.5
C14A—C15A—H15A	118.7	C14B—C15B—H15B	118.5
C15A—C16A—C1A	119.6 (8)	C15B—C16B—C1B	117.5 (8)
C15A—C16A—H16A	120.2	C15B—C16B—H16B	121.2
C1A—C16A—H16A	120.2	C1B—C16B—H16B	121.2
C14A—C17A—H17A	109.5	C14B—C17B—H17D	109.5
C14A—C17A—H17B	109.5	C14B—C17B—H17E	109.5
H17A—C17A—H17B	109.5	H17D—C17B—H17E	109.5
C14A—C17A—H17C	109.5	C14B—C17B—H17F	109.5
H17A—C17A—H17C	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17C	109.5	H17E—C17B—H17F	109.5
C14A—C18A—H18A	109.5	C14B—C18B—H18D	109.5
C14A—C18A—H18B	109.5	C14B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
C14A—C18A—H18C	109.5	C14B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
O6A—C19A—C20A	108.0 (6)	C20B—C19B—C23B	114.0 (8)
O6A—C19A—C22A	109.1 (7)	C20B—C19B—O6B	108.1 (6)
C20A—C19A—C22A	112.7 (7)	C23B—C19B—O6B	104.9 (7)
O6A—C19A—C23A	103.3 (7)	C20B—C19B—C22B	111.7 (7)
C20A—C19A—C23A	110.6 (8)	C23B—C19B—C22B	111.6 (7)
C22A—C19A—C23A	112.6 (7)	O6B—C19B—C22B	106.0 (7)
C21A—C20A—C19A	122.0 (9)	C21B—C20B—C19B	122.5 (7)
C21A—C20A—H20A	119.0	C21B—C20B—H20B	118.8
C19A—C20A—H20A	119.0	C19B—C20B—H20B	118.8
C20A—C21A—C7A	116.9 (9)	C20B—C21B—C7B	119.2 (7)
C20A—C21A—H21A	121.6	C20B—C21B—H21B	120.4
C7A—C21A—H21A	121.6	C7B—C21B—H21B	120.4
C19A—C22A—H22A	109.5	C19B—C22B—H22D	109.5
C19A—C22A—H22B	109.5	C19B—C22B—H22E	109.5
H22A—C22A—H22B	109.5	H22D—C22B—H22E	109.5
C19A—C22A—H22C	109.5	C19B—C22B—H22F	109.5
H22A—C22A—H22C	109.5	H22D—C22B—H22F	109.5
H22B—C22A—H22C	109.5	H22E—C22B—H22F	109.5
C19A—C23A—H23A	109.5	C19B—C23B—H23D	109.5
C19A—C23A—H23B	109.5	C19B—C23B—H23E	109.5
H23A—C23A—H23B	109.5	H23D—C23B—H23E	109.5
C19A—C23A—H23C	109.5	C19B—C23B—H23F	109.5
H23A—C23A—H23C	109.5	H23D—C23B—H23F	109.5
H23B—C23A—H23C	109.5	H23E—C23B—H23F	109.5
C14A—O4A—C2A—C3A	153.0 (7)	C10B—C1B—C2B—O4B	178.1 (7)
C14A—O4A—C2A—C1A	−29.3 (11)	C16B—C1B—C2B—O4B	−1.1 (12)
C16A—C1A—C2A—O4A	−5.1 (12)	C10B—C1B—C2B—C3B	3.3 (12)
C10A—C1A—C2A—O4A	−179.3 (7)	C16B—C1B—C2B—C3B	−175.9 (7)
C16A—C1A—C2A—C3A	172.5 (7)	C14B—O4B—C2B—C1B	33.4 (11)
C10A—C1A—C2A—C3A	−1.7 (12)	C14B—O4B—C2B—C3B	−151.3 (7)
O4A—C2A—C3A—O5A	0.0 (11)	C1B—C2B—C3B—O5B	175.7 (7)
C1A—C2A—C3A—O5A	−177.7 (7)	O4B—C2B—C3B—O5B	0.4 (11)
O4A—C2A—C3A—C4A	−177.6 (7)	C1B—C2B—C3B—C4B	−4.2 (12)
C1A—C2A—C3A—C4A	4.7 (12)	O4B—C2B—C3B—C4B	−179.5 (7)
O5A—C3A—C4A—C11A	178.7 (7)	O5B—C3B—C4B—C11B	−177.6 (7)
C2A—C3A—C4A—C11A	−3.8 (12)	C2B—C3B—C4B—C11B	2.3 (12)
C12A—C5A—C6A—C7A	2.1 (13)	C19B—O6B—C6B—C5B	−153.9 (7)
C12A—C5A—C6A—O6A	−179.4 (7)	C19B—O6B—C6B—C7B	26.5 (11)
C19A—O6A—C6A—C7A	−29.2 (11)	C12B—C5B—C6B—O6B	−179.6 (7)
C19A—O6A—C6A—C5A	152.2 (7)	C12B—C5B—C6B—C7B	0.0 (11)
C5A—C6A—C7A—C8A	−1.2 (13)	O6B—C6B—C7B—C8B	179.1 (7)
O6A—C6A—C7A—C8A	−179.6 (7)	C5B—C6B—C7B—C8B	−0.5 (12)
C5A—C6A—C7A—C21A	176.5 (8)	O6B—C6B—C7B—C21B	3.9 (11)
O6A—C6A—C7A—C21A	−1.9 (12)	C5B—C6B—C7B—C21B	−175.7 (7)
C6A—C7A—C8A—O3A	−178.4 (8)	C6B—C7B—C8B—O3B	−178.4 (7)
C21A—C7A—C8A—O3A	3.8 (12)	C21B—C7B—C8B—O3B	−3.5 (11)
C6A—C7A—C8A—C13A	−0.9 (12)	C6B—C7B—C8B—C13B	0.3 (11)
C21A—C7A—C8A—C13A	−178.7 (7)	C21B—C7B—C8B—C13B	175.1 (7)
C2A—C1A—C10A—C11A	−2.1 (12)	C2B—C1B—C10B—C11B	−0.7 (11)
C16A—C1A—C10A—C11A	−175.6 (8)	C16B—C1B—C10B—C11B	178.5 (7)
C2A—C1A—C10A—C9A	177.4 (7)	C2B—C1B—C10B—C9B	−178.7 (7)
C16A—C1A—C10A—C9A	4.0 (13)	C16B—C1B—C10B—C9B	0.4 (13)
O2A—C9A—C10A—C11A	177.6 (9)	O2B—C9B—C10B—C11B	179.5 (7)
C13A—C9A—C10A—C11A	−0.6 (11)	C13B—C9B—C10B—C11B	0.0 (10)
O2A—C9A—C10A—C1A	−1.9 (13)	O2B—C9B—C10B—C1B	−2.5 (13)
C13A—C9A—C10A—C1A	179.8 (7)	C13B—C9B—C10B—C1B	178.0 (7)
C3A—C4A—C11A—C10A	−0.2 (13)	C3B—C4B—C11B—O1B	−179.6 (7)
C3A—C4A—C11A—O1A	−179.0 (7)	C3B—C4B—C11B—C10B	0.3 (12)
C1A—C10A—C11A—C4A	3.1 (13)	C12B—O1B—C11B—C4B	−175.6 (7)
C9A—C10A—C11A—C4A	−176.4 (8)	C12B—O1B—C11B—C10B	4.6 (11)
C1A—C10A—C11A—O1A	−178.1 (7)	C1B—C10B—C11B—C4B	−1.1 (12)
C9A—C10A—C11A—O1A	2.3 (12)	C9B—C10B—C11B—C4B	177.0 (7)
C12A—O1A—C11A—C4A	177.5 (7)	C1B—C10B—C11B—O1B	178.7 (7)
C12A—O1A—C11A—C10A	−1.4 (12)	C9B—C10B—C11B—O1B	−3.2 (11)
C11A—O1A—C12A—C13A	−1.4 (12)	C11B—O1B—C12B—C5B	177.2 (6)
C11A—O1A—C12A—C5A	−179.1 (7)	C11B—O1B—C12B—C13B	−2.7 (11)
C6A—C5A—C12A—C13A	−0.8 (13)	C6B—C5B—C12B—O1B	−179.2 (7)
C6A—C5A—C12A—O1A	177.0 (7)	C6B—C5B—C12B—C13B	0.8 (12)
O1A—C12A—C13A—C8A	−178.8 (8)	O3B—C8B—C13B—C12B	179.0 (7)
C5A—C12A—C13A—C8A	−1.3 (13)	C7B—C8B—C13B—C12B	0.5 (11)
O1A—C12A—C13A—C9A	3.1 (14)	O3B—C8B—C13B—C9B	−1.6 (11)
C5A—C12A—C13A—C9A	−179.3 (7)	C7B—C8B—C13B—C9B	179.8 (7)
O3A—C8A—C13A—C12A	179.6 (8)	O1B—C12B—C13B—C8B	178.9 (7)
C7A—C8A—C13A—C12A	2.2 (13)	C5B—C12B—C13B—C8B	−1.0 (11)
O3A—C8A—C13A—C9A	−2.3 (13)	O1B—C12B—C13B—C9B	−0.5 (11)
C7A—C8A—C13A—C9A	−179.7 (7)	C5B—C12B—C13B—C9B	179.6 (7)
O2A—C9A—C13A—C12A	179.6 (8)	O2B—C9B—C13B—C8B	2.9 (11)
C10A—C9A—C13A—C12A	−2.0 (12)	C10B—C9B—C13B—C8B	−177.6 (7)
O2A—C9A—C13A—C8A	1.5 (12)	O2B—C9B—C13B—C12B	−177.7 (7)
C10A—C9A—C13A—C8A	179.9 (7)	C10B—C9B—C13B—C12B	1.8 (11)
C2A—O4A—C14A—C18A	166.4 (7)	C2B—O4B—C14B—C15B	−48.5 (9)
C2A—O4A—C14A—C17A	−73.7 (9)	C2B—O4B—C14B—C17B	74.5 (8)
C2A—O4A—C14A—C15A	45.5 (9)	C2B—O4B—C14B—C18B	−166.3 (7)
O4A—C14A—C15A—C16A	−34.4 (11)	O4B—C14B—C15B—C16B	38.8 (11)
C18A—C14A—C15A—C16A	−151.7 (8)	C17B—C14B—C15B—C16B	−82.7 (10)
C17A—C14A—C15A—C16A	82.2 (10)	C18B—C14B—C15B—C16B	151.2 (8)
C14A—C15A—C16A—C1A	3.6 (13)	C14B—C15B—C16B—C1B	−8.3 (12)
C2A—C1A—C16A—C15A	18.1 (12)	C2B—C1B—C16B—C15B	−12.5 (11)
C10A—C1A—C16A—C15A	−168.4 (8)	C10B—C1B—C16B—C15B	168.3 (8)
C6A—O6A—C19A—C20A	46.9 (9)	C6B—O6B—C19B—C20B	−41.9 (10)
C6A—O6A—C19A—C22A	−75.9 (8)	C6B—O6B—C19B—C23B	−163.9 (7)
C6A—O6A—C19A—C23A	164.1 (7)	C6B—O6B—C19B—C22B	77.9 (8)
O6A—C19A—C20A—C21A	−40.2 (11)	C23B—C19B—C20B—C21B	147.1 (9)
C22A—C19A—C20A—C21A	80.4 (10)	O6B—C19B—C20B—C21B	30.9 (12)
C23A—C19A—C20A—C21A	−152.6 (8)	C22B—C19B—C20B—C21B	−85.3 (11)
C19A—C20A—C21A—C7A	12.1 (12)	C19B—C20B—C21B—C7B	−4.3 (14)
C6A—C7A—C21A—C20A	10.9 (12)	C8B—C7B—C21B—C20B	169.7 (8)
C8A—C7A—C21A—C20A	−171.4 (8)	C6B—C7B—C21B—C20B	−15.4 (12)

Cg5 and Cg20 are the centroids of C5A–C8A/C12A/C13A and C5B–C8B/C12B/C13B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3A—H3AA···O2A	0.82	1.84	2.571 (9)	147
O5A—H5AA···O4A	0.82	2.19	2.656 (9)	116
O3B—H3BA···O2B	0.82	1.84	2.559 (9)	146
O5B—H5BA···O4B	0.82	2.15	2.628 (8)	117
C15B—H15B···O2Ai	0.93	2.60	3.514 (11)	168
C16A—H16A···O2A	0.93	2.29	2.879 (11)	121
C16B—H16B···O2B	0.93	2.31	2.890 (10)	120
C17B—H17E···O5Bi	0.96	2.58	3.441 (10)	149
C23B—H23D···O1Aii	0.96	2.59	3.370 (11)	139
C18A—H18B···Cg20	0.96	2.75	3.611 (10)	150
C18B—H18D···Cg5	0.96	2.79	3.662 (9)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg5 and Cg20 are the centroids of C5A–C8A/C12A/C13A and C5B–C8B/C12B/C13B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3A—H3AA⋯O2A	0.82	1.84	2.571 (9)	147
O5A—H5AA⋯O4A	0.82	2.19	2.656 (9)	116
O3B—H3BA⋯O2B	0.82	1.84	2.559 (9)	146
O5B—H5BA⋯O4B	0.82	2.15	2.628 (8)	117
C15B—H15B⋯O2Ai	0.93	2.60	3.514 (11)	168
C16A—H16A⋯O2A	0.93	2.29	2.879 (11)	121
C16B—H16B⋯O2B	0.93	2.31	2.890 (10)	120
C17B—H17E⋯O5Bi	0.96	2.58	3.441 (10)	149
C23B—H23D⋯O1Aii	0.96	2.59	3.370 (11)	139
C18A—H18B⋯Cg20	0.96	2.75	3.611 (10)	150
C18B—H18D⋯Cg5	0.96	2.79	3.662 (9)	152

Symmetry codes: (i) ; (ii) .