3,3-Dimethyl-cis-9a,13a-diphenyl-2,3,9a,11,12,13a-hexa-hydro-1H-benzo[h][1,4]dioxino[2',3':5,6][1,4]dioxino[2,3-f]chromene.

In the title di-hydro-dioxin, C31H28O5, the dioxane ring has a chair conformation, whereas each of the pyran and dioxine rings has an envelope conformation with methyl-ene and quaternary C atoms, respectively, being the flap atoms. The phenyl rings are cis and form a dihedral angle of 82.11 (10)°. The molecular structure is stabilized by C-H⋯O contacts. In the crystal packing, supra-molecular layers parallel to (101) are sustained by C-H⋯π inter-actions.

Related literature

For the biological activity of lapachol and its isomers, see: de Almeida (2009 ▶); Ferreira et al. (2010 ▶); Medeiros et al. (2010 ▶); Neves-Pinto et al. (2002 ▶). For reactions of the quinone O atoms in lapachol, see: da Silva et al. (2011 ▶); Ferreira et al. (2006 ▶); Neves-Pinto et al. (2002 ▶). For the preparation of di­hydro­dioxins, see: Schönberg & Mustafa (1944 ▶), and for their DNA photo-cleavage, see: Mack et al. (2004 ▶). For the synthesis, see: Summerbell & Berger (1959 ▶). For the crystal structure of β-lapachone, see: Cunha-Filho et al. (2006 ▶).

Experimental

Crystal data

C31H28O5

M = 480.53

Monoclinic,

a = 15.1335 (6) Å

b = 9.6048 (2) Å

c = 16.9739 (6) Å

β = 97.384 (1)°

V = 2446.77 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.36 × 0.28 × 0.07 mm

Data collection

Bruker-Nonius Roper CCD camera on a κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.831, T max = 1.000

23103 measured reflections

5549 independent reflections

3390 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.139

S = 1.02

5549 reflections

355 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536813023660/hg5343sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023660/hg5343Isup2.hkl

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

C31H28O5	F(000) = 1016
Mr = 480.53	Dx = 1.304 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5547 reflections
a = 15.1335 (6) Å	θ = 2.9–27.5°
b = 9.6048 (2) Å	µ = 0.09 mm−1
c = 16.9739 (6) Å	T = 120 K
β = 97.384 (1)°	Slab, colourless
V = 2446.77 (14) Å3	0.36 × 0.28 × 0.07 mm
Z = 4

Bruker-Nonius Roper CCD camera on a κ-goniostat diffractometer	5549 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	3390 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 9.091 pixels mm-1	θmax = 27.4°, θmin = 3.2°
φ & ω scans	h = −15→19
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −12→12
Tmin = 0.831, Tmax = 1.000	l = −21→21
23103 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0726P)2] where P = (Fo2 + 2Fc2)/3
5549 reflections	(Δ/σ)max < 0.001
355 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.07265 (9)	0.34146 (11)	0.23877 (7)	0.0227 (3)
O2	0.17388 (8)	0.21646 (11)	−0.00687 (7)	0.0212 (3)
O3	0.22585 (8)	−0.04598 (11)	0.05583 (7)	0.0197 (3)
O4	0.16943 (9)	0.13692 (12)	−0.13294 (7)	0.0241 (3)
O5	0.10415 (8)	−0.05976 (11)	−0.03375 (7)	0.0220 (3)
C2	0.03141 (13)	0.46851 (17)	0.20263 (11)	0.0249 (4)
C3	0.09216 (14)	0.52936 (17)	0.14656 (11)	0.0272 (5)
H3A	0.1507	0.5521	0.1769	0.031 (5)*
H3B	0.0658	0.6168	0.1232	0.030 (5)*
C4	0.10551 (14)	0.42770 (17)	0.08004 (11)	0.0246 (4)
H4A	0.0510	0.4243	0.0410	0.025 (5)*
H4B	0.1555	0.4595	0.0522	0.024 (5)*
C4A	0.12557 (12)	0.28463 (16)	0.11431 (10)	0.0188 (4)
C5	0.18803 (12)	0.05363 (16)	0.10082 (10)	0.0172 (4)
C6	0.16391 (12)	0.18128 (17)	0.06989 (10)	0.0184 (4)
C6A	0.17505 (12)	0.01886 (16)	0.17947 (10)	0.0171 (4)
C7	0.19548 (12)	−0.11445 (17)	0.21269 (10)	0.0200 (4)
H7	0.2207	−0.1834	0.1823	0.013 (4)*
C8	0.17912 (12)	−0.14461 (18)	0.28843 (10)	0.0231 (4)
H8	0.1916	−0.2351	0.3095	0.019 (5)*
C9	0.14399 (13)	−0.04266 (18)	0.33515 (11)	0.0253 (5)
H9	0.1342	−0.0639	0.3880	0.036 (6)*
C10	0.12390 (13)	0.08757 (17)	0.30443 (10)	0.0216 (4)
H10	0.1010	0.1562	0.3366	0.031 (5)*
C10A	0.13687 (12)	0.12094 (17)	0.22567 (10)	0.0181 (4)
C10B	0.11111 (12)	0.25221 (17)	0.19031 (10)	0.0184 (4)
C11	0.02511 (16)	0.56118 (19)	0.27419 (12)	0.0355 (5)
H11A	0.0849	0.5773	0.3023	0.046 (7)*
H11B	−0.0118	0.5156	0.3100	0.035 (6)*
H11C	−0.0018	0.6504	0.2564	0.046 (6)*
C12	−0.06075 (14)	0.4327 (2)	0.16053 (13)	0.0343 (5)
H12A	−0.0552	0.3644	0.1185	0.045 (6)*
H12B	−0.0893	0.5172	0.1371	0.040 (6)*
H12C	−0.0971	0.3933	0.1989	0.033 (6)*
C13	0.21410 (13)	0.11661 (18)	−0.05551 (10)	0.0207 (4)
C14	0.07502 (13)	0.10801 (18)	−0.13920 (11)	0.0267 (5)
H14A	0.0477	0.1202	−0.1950	0.026 (5)*
H14B	0.0464	0.1745	−0.1058	0.034 (5)*
C15	0.05956 (14)	−0.03797 (18)	−0.11270 (11)	0.0256 (5)
H15A	−0.0051	−0.0544	−0.1136	0.031 (5)*
H15B	0.0823	−0.1049	−0.1496	0.022 (5)*
C16	0.19741 (12)	−0.03490 (17)	−0.02661 (10)	0.0193 (4)
C17	0.31092 (13)	0.15683 (17)	−0.05503 (10)	0.0220 (4)
C18	0.37148 (16)	0.1396 (3)	0.01208 (12)	0.0485 (7)
H18	0.3530	0.0973	0.0578	0.069 (8)*
C19	0.45920 (16)	0.1832 (3)	0.01376 (13)	0.0561 (7)
H19	0.5001	0.1697	0.0605	0.082 (9)*
C20	0.48716 (16)	0.2452 (2)	−0.05084 (13)	0.0407 (6)
H20	0.5471	0.2755	−0.0494	0.053 (7)*
C21	0.42738 (15)	0.2634 (2)	−0.11828 (14)	0.0427 (6)
H21	0.4464	0.3058	−0.1638	0.048 (6)*
C22	0.33982 (14)	0.2206 (2)	−0.12029 (13)	0.0341 (5)
H22	0.2991	0.2351	−0.1670	0.050 (7)*
C23	0.24471 (13)	−0.15056 (17)	−0.06662 (10)	0.0216 (4)
C24	0.27317 (14)	−0.13653 (19)	−0.14065 (11)	0.0285 (5)
H24	0.2670	−0.0496	−0.1674	0.042 (6)*
C25	0.31066 (14)	−0.2488 (2)	−0.17594 (12)	0.0321 (5)
H25	0.3301	−0.2380	−0.2266	0.045 (6)*
C26	0.31977 (15)	−0.3756 (2)	−0.13795 (12)	0.0345 (5)
H26	0.3456	−0.4520	−0.1622	0.038 (6)*
C27	0.29106 (15)	−0.3912 (2)	−0.06409 (12)	0.0351 (5)
H27	0.2971	−0.4786	−0.0377	0.037 (6)*
C28	0.25370 (13)	−0.28000 (18)	−0.02881 (12)	0.0282 (5)
H28	0.2339	−0.2916	0.0217	0.031 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0249 (8)	0.0204 (6)	0.0237 (7)	0.0053 (5)	0.0061 (6)	−0.0014 (5)
O2	0.0252 (8)	0.0203 (6)	0.0191 (7)	0.0007 (5)	0.0068 (6)	0.0029 (5)
O3	0.0209 (8)	0.0211 (6)	0.0173 (6)	0.0028 (5)	0.0035 (5)	−0.0014 (5)
O4	0.0229 (8)	0.0300 (7)	0.0189 (7)	−0.0040 (5)	0.0003 (6)	0.0026 (5)
O5	0.0152 (7)	0.0267 (6)	0.0234 (7)	−0.0026 (5)	−0.0002 (6)	0.0017 (5)
C2	0.0244 (12)	0.0183 (9)	0.0323 (11)	0.0036 (8)	0.0051 (9)	−0.0006 (8)
C3	0.0301 (12)	0.0177 (9)	0.0344 (11)	0.0019 (8)	0.0058 (10)	0.0010 (8)
C4	0.0273 (12)	0.0212 (9)	0.0260 (10)	0.0019 (8)	0.0056 (9)	0.0024 (8)
C4A	0.0154 (10)	0.0187 (9)	0.0220 (10)	−0.0021 (7)	0.0007 (8)	0.0016 (7)
C5	0.0141 (10)	0.0186 (9)	0.0191 (9)	0.0001 (7)	0.0024 (8)	−0.0031 (7)
C6	0.0156 (10)	0.0229 (9)	0.0169 (9)	−0.0050 (7)	0.0029 (8)	0.0002 (7)
C6A	0.0132 (10)	0.0186 (8)	0.0189 (9)	−0.0028 (7)	0.0001 (8)	0.0009 (7)
C7	0.0170 (11)	0.0191 (9)	0.0233 (10)	0.0008 (7)	0.0003 (8)	−0.0004 (7)
C8	0.0186 (11)	0.0246 (10)	0.0251 (10)	0.0022 (8)	−0.0007 (8)	0.0064 (8)
C9	0.0229 (12)	0.0327 (11)	0.0208 (10)	0.0005 (8)	0.0044 (9)	0.0051 (8)
C10	0.0194 (11)	0.0250 (9)	0.0210 (10)	0.0006 (8)	0.0044 (8)	−0.0020 (8)
C10A	0.0138 (10)	0.0213 (9)	0.0190 (9)	−0.0019 (7)	0.0010 (8)	−0.0007 (7)
C10B	0.0135 (10)	0.0201 (8)	0.0213 (10)	−0.0004 (7)	0.0011 (8)	−0.0031 (7)
C11	0.0412 (15)	0.0277 (11)	0.0398 (13)	0.0035 (10)	0.0137 (11)	−0.0045 (9)
C12	0.0246 (13)	0.0333 (11)	0.0444 (13)	0.0052 (9)	0.0025 (10)	0.0053 (10)
C13	0.0203 (11)	0.0269 (9)	0.0154 (9)	−0.0005 (8)	0.0048 (8)	−0.0017 (7)
C14	0.0211 (12)	0.0299 (10)	0.0272 (11)	−0.0021 (8)	−0.0042 (9)	0.0037 (8)
C15	0.0205 (12)	0.0304 (10)	0.0237 (10)	−0.0015 (8)	−0.0049 (9)	0.0001 (8)
C16	0.0164 (11)	0.0257 (9)	0.0156 (9)	−0.0034 (7)	0.0012 (8)	0.0000 (7)
C17	0.0204 (11)	0.0238 (9)	0.0225 (10)	−0.0036 (8)	0.0057 (9)	−0.0035 (7)
C18	0.0318 (15)	0.0891 (18)	0.0237 (12)	−0.0267 (13)	0.0000 (11)	0.0119 (11)
C19	0.0288 (15)	0.110 (2)	0.0274 (13)	−0.0285 (14)	−0.0049 (11)	0.0131 (13)
C20	0.0234 (13)	0.0611 (14)	0.0387 (13)	−0.0159 (11)	0.0079 (11)	−0.0002 (11)
C21	0.0281 (14)	0.0603 (14)	0.0405 (14)	−0.0078 (11)	0.0072 (11)	0.0179 (11)
C22	0.0230 (12)	0.0445 (12)	0.0344 (12)	−0.0028 (9)	0.0027 (10)	0.0121 (9)
C23	0.0171 (11)	0.0250 (10)	0.0222 (10)	−0.0012 (8)	0.0005 (8)	−0.0057 (7)
C24	0.0295 (13)	0.0298 (10)	0.0262 (11)	−0.0041 (9)	0.0033 (9)	−0.0061 (8)
C25	0.0295 (13)	0.0384 (12)	0.0295 (12)	−0.0050 (9)	0.0081 (10)	−0.0128 (9)
C26	0.0334 (13)	0.0337 (11)	0.0358 (12)	0.0060 (9)	0.0021 (10)	−0.0154 (9)
C27	0.0420 (15)	0.0278 (11)	0.0347 (12)	0.0109 (9)	0.0014 (11)	−0.0049 (9)
C28	0.0290 (13)	0.0303 (11)	0.0250 (11)	0.0032 (8)	0.0028 (9)	−0.0037 (8)

O1—C10B	1.369 (2)	C11—H11B	0.9800
O1—C2	1.468 (2)	C11—H11C	0.9800
O2—C6	1.373 (2)	C12—H12A	0.9800
O2—C13	1.449 (2)	C12—H12B	0.9800
O3—C5	1.3923 (19)	C12—H12C	0.9800
O3—C16	1.414 (2)	C13—C17	1.514 (3)
O4—C13	1.412 (2)	C13—C16	1.567 (2)
O4—C14	1.446 (2)	C14—C15	1.500 (2)
O5—C16	1.421 (2)	C14—H14A	0.9900
O5—C15	1.436 (2)	C14—H14B	0.9900
C2—C11	1.519 (3)	C15—H15A	0.9900
C2—C12	1.523 (3)	C15—H15B	0.9900
C2—C3	1.522 (3)	C16—C23	1.527 (2)
C3—C4	1.526 (2)	C17—C18	1.377 (3)
C3—H3A	0.9900	C17—C22	1.385 (3)
C3—H3B	0.9900	C18—C19	1.389 (3)
C4—C4A	1.508 (2)	C18—H18	0.9500
C4—H4A	0.9900	C19—C20	1.362 (3)
C4—H4B	0.9900	C19—H19	0.9500
C4A—C10B	1.372 (2)	C20—C21	1.376 (3)
C4A—C6	1.415 (2)	C20—H20	0.9500
C5—C6	1.365 (2)	C21—C22	1.384 (3)
C5—C6A	1.414 (2)	C21—H21	0.9500
C6A—C7	1.417 (2)	C22—H22	0.9500
C6A—C10A	1.424 (2)	C23—C24	1.386 (3)
C7—C8	1.371 (2)	C23—C28	1.398 (3)
C7—H7	0.9500	C24—C25	1.390 (3)
C8—C9	1.407 (2)	C24—H24	0.9500
C8—H8	0.9500	C25—C26	1.376 (3)
C9—C10	1.374 (2)	C25—H25	0.9500
C9—H9	0.9500	C26—C27	1.387 (3)
C10—C10A	1.413 (2)	C26—H26	0.9500
C10—H10	0.9500	C27—C28	1.381 (3)
C10A—C10B	1.429 (2)	C27—H27	0.9500
C11—H11A	0.9800	C28—H28	0.9500
C10B—O1—C2	117.40 (13)	H12A—C12—H12C	109.5
C6—O2—C13	118.89 (12)	H12B—C12—H12C	109.5
C5—O3—C16	113.37 (12)	O4—C13—O2	104.65 (13)
C13—O4—C14	113.10 (13)	O4—C13—C17	108.48 (14)
C16—O5—C15	113.43 (13)	O2—C13—C17	107.76 (13)
O1—C2—C11	102.70 (15)	O4—C13—C16	110.04 (13)
O1—C2—C12	108.83 (14)	O2—C13—C16	109.86 (13)
C11—C2—C12	111.10 (17)	C17—C13—C16	115.48 (15)
O1—C2—C3	108.77 (15)	O4—C14—C15	110.38 (15)
C11—C2—C3	112.34 (15)	O4—C14—H14A	109.6
C12—C2—C3	112.56 (17)	C15—C14—H14A	109.6
C2—C3—C4	111.41 (15)	O4—C14—H14B	109.6
C2—C3—H3A	109.3	C15—C14—H14B	109.6
C4—C3—H3A	109.3	H14A—C14—H14B	108.1
C2—C3—H3B	109.3	O5—C15—C14	110.08 (14)
C4—C3—H3B	109.3	O5—C15—H15A	109.6
H3A—C3—H3B	108.0	C14—C15—H15A	109.6
C4A—C4—C3	109.69 (15)	O5—C15—H15B	109.6
C4A—C4—H4A	109.7	C14—C15—H15B	109.6
C3—C4—H4A	109.7	H15A—C15—H15B	108.2
C4A—C4—H4B	109.7	O3—C16—O5	104.15 (13)
C3—C4—H4B	109.7	O3—C16—C23	106.55 (13)
H4A—C4—H4B	108.2	O5—C16—C23	110.91 (13)
C10B—C4A—C6	117.89 (15)	O3—C16—C13	109.81 (13)
C10B—C4A—C4	121.41 (15)	O5—C16—C13	109.13 (14)
C6—C4A—C4	120.64 (15)	C23—C16—C13	115.64 (14)
C6—C5—O3	120.98 (15)	C18—C17—C22	118.01 (18)
C6—C5—C6A	120.83 (15)	C18—C17—C13	120.96 (16)
O3—C5—C6A	118.18 (14)	C22—C17—C13	120.89 (17)
C5—C6—O2	121.97 (15)	C17—C18—C19	120.9 (2)
C5—C6—C4A	122.20 (15)	C17—C18—H18	119.6
O2—C6—C4A	115.82 (14)	C19—C18—H18	119.6
C5—C6A—C7	122.64 (15)	C20—C19—C18	120.7 (2)
C5—C6A—C10A	118.22 (15)	C20—C19—H19	119.7
C7—C6A—C10A	119.10 (15)	C18—C19—H19	119.7
C8—C7—C6A	120.50 (16)	C19—C20—C21	119.1 (2)
C8—C7—H7	119.7	C19—C20—H20	120.5
C6A—C7—H7	119.7	C21—C20—H20	120.5
C7—C8—C9	120.56 (16)	C20—C21—C22	120.5 (2)
C7—C8—H8	119.7	C20—C21—H21	119.7
C9—C8—H8	119.7	C22—C21—H21	119.7
C10—C9—C8	120.06 (16)	C21—C22—C17	120.8 (2)
C10—C9—H9	120.0	C21—C22—H22	119.6
C8—C9—H9	120.0	C17—C22—H22	119.6
C9—C10—C10A	120.97 (16)	C24—C23—C28	118.65 (16)
C9—C10—H10	119.5	C24—C23—C16	123.39 (16)
C10A—C10—H10	119.5	C28—C23—C16	117.79 (16)
C10—C10A—C6A	118.73 (15)	C23—C24—C25	120.46 (18)
C10—C10A—C10B	122.27 (15)	C23—C24—H24	119.8
C6A—C10A—C10B	118.98 (15)	C25—C24—H24	119.8
O1—C10B—C4A	123.68 (15)	C26—C25—C24	120.42 (19)
O1—C10B—C10A	114.48 (14)	C26—C25—H25	119.8
C4A—C10B—C10A	121.83 (15)	C24—C25—H25	119.8
C2—C11—H11A	109.5	C25—C26—C27	119.69 (18)
C2—C11—H11B	109.5	C25—C26—H26	120.2
H11A—C11—H11B	109.5	C27—C26—H26	120.2
C2—C11—H11C	109.5	C28—C27—C26	120.10 (19)
H11A—C11—H11C	109.5	C28—C27—H27	119.9
H11B—C11—H11C	109.5	C26—C27—H27	119.9
C2—C12—H12A	109.5	C27—C28—C23	120.67 (18)
C2—C12—H12B	109.5	C27—C28—H28	119.7
H12A—C12—H12B	109.5	C23—C28—H28	119.7
C2—C12—H12C	109.5
C10B—O1—C2—C11	−161.60 (15)	C6—O2—C13—O4	145.39 (14)
C10B—O1—C2—C12	80.58 (19)	C6—O2—C13—C17	−99.29 (17)
C10B—O1—C2—C3	−42.4 (2)	C6—O2—C13—C16	27.3 (2)
O1—C2—C3—C4	60.8 (2)	C13—O4—C14—C15	−56.94 (18)
C11—C2—C3—C4	173.82 (16)	C16—O5—C15—C14	−57.79 (19)
C12—C2—C3—C4	−59.9 (2)	O4—C14—C15—O5	55.3 (2)
C2—C3—C4—C4A	−46.2 (2)	C5—O3—C16—O5	−62.68 (16)
C3—C4—C4A—C10B	14.3 (2)	C5—O3—C16—C23	−179.99 (13)
C3—C4—C4A—C6	−162.79 (17)	C5—O3—C16—C13	54.07 (18)
C16—O3—C5—C6	−29.5 (2)	C15—O5—C16—O3	173.41 (12)
C16—O3—C5—C6A	150.33 (15)	C15—O5—C16—C23	−72.34 (16)
O3—C5—C6—O2	1.4 (3)	C15—O5—C16—C13	56.18 (16)
C6A—C5—C6—O2	−178.46 (16)	O4—C13—C16—O3	−167.72 (13)
O3—C5—C6—C4A	−179.82 (16)	O2—C13—C16—O3	−53.02 (18)
C6A—C5—C6—C4A	0.3 (3)	C17—C13—C16—O3	69.09 (18)
C13—O2—C6—C5	−2.2 (2)	O4—C13—C16—O5	−54.14 (17)
C13—O2—C6—C4A	178.95 (15)	O2—C13—C16—O5	60.56 (17)
C10B—C4A—C6—C5	−1.3 (3)	C17—C13—C16—O5	−177.33 (13)
C4—C4A—C6—C5	175.85 (17)	O4—C13—C16—C23	71.70 (19)
C10B—C4A—C6—O2	177.52 (16)	O2—C13—C16—C23	−173.60 (14)
C4—C4A—C6—O2	−5.3 (2)	C17—C13—C16—C23	−51.5 (2)
C6—C5—C6A—C7	177.14 (17)	O4—C13—C17—C18	−176.17 (18)
O3—C5—C6A—C7	−2.7 (3)	O2—C13—C17—C18	71.1 (2)
C6—C5—C6A—C10A	−0.5 (3)	C16—C13—C17—C18	−52.2 (2)
O3—C5—C6A—C10A	179.63 (15)	O4—C13—C17—C22	8.2 (2)
C5—C6A—C7—C8	−177.93 (18)	O2—C13—C17—C22	−104.54 (18)
C10A—C6A—C7—C8	−0.3 (3)	C16—C13—C17—C22	132.24 (18)
C6A—C7—C8—C9	−1.7 (3)	C22—C17—C18—C19	−0.9 (3)
C7—C8—C9—C10	1.5 (3)	C13—C17—C18—C19	−176.6 (2)
C8—C9—C10—C10A	0.8 (3)	C17—C18—C19—C20	0.6 (4)
C9—C10—C10A—C6A	−2.8 (3)	C18—C19—C20—C21	−0.4 (4)
C9—C10—C10A—C10B	175.73 (17)	C19—C20—C21—C22	0.6 (4)
C5—C6A—C10A—C10	−179.76 (16)	C20—C21—C22—C17	−0.9 (3)
C7—C6A—C10A—C10	2.5 (3)	C18—C17—C22—C21	1.1 (3)
C5—C6A—C10A—C10B	1.7 (2)	C13—C17—C22—C21	176.80 (19)
C7—C6A—C10A—C10B	−176.06 (16)	O3—C16—C23—C24	−145.17 (17)
C2—O1—C10B—C4A	10.7 (2)	O5—C16—C23—C24	102.1 (2)
C2—O1—C10B—C10A	−170.26 (15)	C13—C16—C23—C24	−22.8 (2)
C6—C4A—C10B—O1	−178.42 (16)	O3—C16—C23—C28	39.6 (2)
C4—C4A—C10B—O1	4.4 (3)	O5—C16—C23—C28	−73.1 (2)
C6—C4A—C10B—C10A	2.6 (3)	C13—C16—C23—C28	161.93 (16)
C4—C4A—C10B—C10A	−174.60 (16)	C28—C23—C24—C25	−0.6 (3)
C10—C10A—C10B—O1	−0.4 (2)	C16—C23—C24—C25	−175.84 (18)
C6A—C10A—C10B—O1	178.11 (15)	C23—C24—C25—C26	0.2 (3)
C10—C10A—C10B—C4A	178.70 (17)	C24—C25—C26—C27	0.2 (3)
C6A—C10A—C10B—C4A	−2.8 (3)	C25—C26—C27—C28	−0.1 (3)
C14—O4—C13—O2	−62.31 (16)	C26—C27—C28—C23	−0.3 (3)
C14—O4—C13—C17	−177.13 (13)	C24—C23—C28—C27	0.7 (3)
C14—O4—C13—C16	55.67 (17)	C16—C23—C28—C27	176.17 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O3	0.95	2.36	3.001 (3)	124
C22—H22···O4	0.95	2.32	2.683 (3)	102
C24—H24···O4	0.95	2.44	3.071 (2)	124
C8—H8···Cg1i	0.95	2.65	3.3134 (19)	128
C15—H15A···Cg1ii	0.99	2.39	3.336 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4A,C5,C6,C6A,C10A,C10B benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O3	0.95	2.36	3.001 (3)	124
C22—H22⋯O4	0.95	2.32	2.683 (3)	102
C24—H24⋯O4	0.95	2.44	3.071 (2)	124
C8—H8⋯Cg1i	0.95	2.65	3.3134 (19)	128
C15—H15A⋯Cg1ii	0.99	2.39	3.336 (2)	161

Symmetry codes: (i) ; (ii) .