(6bS*,14R*,14aR*)-Methyl 14-(4-methyl-phen-yl)-7-oxo-6b,6c,7,12b,14,14a-hexa-hydro-1H-pyrano[3,2-c:5,4-c']dichromene-14a-carboxyl-ate.

In the title compound, C(28)H(22)O(6), the chromeno ring system is almost planar, with a dihedral angle between the mean planes of the pyran and benzene rings of 1.87 (8)°. The pyran ring bearing the methyl-phenyl substituent has a half-chair conformation while the other pyran ring has an envelope conformation with the tetra-substituted C atom as the flap. The benzene ring of the chromeno ring system is inclined to the benzene ring fused to the latter pyran ring by 74.66 (9)°. These aromatic rings are inclined to the 4-methyl-phenyl ring by 52.67 (9) and 66.63 (10)°, respectively. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.

Related literature

For the biological importance of 4H-chromene derivatives, see: Cai et al. (2006 ▶); Cai (2007 ▶, 2008 ▶); Gabor (1988 ▶); Brooks (1998 ▶); Valenti et al. (1993 ▶); Hyana & Saimoto (1987 ▶); Tang et al. (2007 ▶).

Experimental

Crystal data

C28H22O6

M = 454.46

Monoclinic,

a = 9.526 (5) Å

b = 10.711 (5) Å

c = 21.975 (5) Å

β = 97.397 (5)°

V = 2223.5 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.32 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.972, T max = 0.992

22624 measured reflections

4741 independent reflections

3251 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.133

S = 1.01

4741 reflections

324 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001244/su2541sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001244/su2541Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001244/su2541Isup3.cml

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

C28H22O6	F(000) = 952
Mr = 454.46	Dx = 1.358 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5710 reflections
a = 9.526 (5) Å	θ = 1.8–28.5°
b = 10.711 (5) Å	µ = 0.10 mm−1
c = 21.975 (5) Å	T = 293 K
β = 97.397 (5)°	Monoclinic, colourless
V = 2223.5 (16) Å3	0.32 × 0.20 × 0.10 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4741 independent reflections
Radiation source: fine-focus sealed tube	3251 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 26.8°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→11
Tmin = 0.972, Tmax = 0.992	k = −13→13
22624 measured reflections	l = −26→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.4826P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
4741 reflections	Δρmax = 0.29 e Å−3
324 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (10)

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.

	x	y	z	Uiso*/Ueq
O1	0.48425 (14)	0.87273 (11)	0.09194 (5)	0.0573 (3)
O2	0.67296 (15)	0.85457 (12)	0.04518 (6)	0.0658 (4)
O3	0.22158 (12)	0.85200 (11)	−0.07008 (5)	0.0544 (3)
O4	0.43549 (15)	0.53003 (11)	−0.09744 (6)	0.0657 (4)
O5	0.4359 (2)	0.65360 (13)	−0.21784 (6)	0.0918 (6)
O6	0.51056 (15)	0.84702 (11)	−0.20115 (6)	0.0647 (4)
C1	0.1064 (2)	0.89144 (18)	0.03761 (9)	0.0603 (5)
H1	0.0445	0.8860	0.0014	0.072*
C2	0.0543 (2)	0.9138 (2)	0.09163 (10)	0.0710 (6)
H2	−0.0425	0.9239	0.0922	0.085*
C3	0.1467 (3)	0.9215 (2)	0.14565 (10)	0.0733 (6)
H3	0.1113	0.9371	0.1824	0.088*
C4	0.2887 (2)	0.90663 (18)	0.14566 (8)	0.0653 (5)
H4	0.3500	0.9114	0.1821	0.078*
C5	0.3403 (2)	0.88433 (15)	0.09076 (8)	0.0511 (4)
C6	0.25104 (19)	0.87658 (14)	0.03612 (7)	0.0491 (4)
C7	0.31477 (18)	0.85169 (14)	−0.01846 (7)	0.0468 (4)
C8	0.45453 (18)	0.82799 (14)	−0.01720 (7)	0.0454 (4)
C9	0.5464 (2)	0.85058 (15)	0.03936 (8)	0.0507 (4)
C10	0.51915 (18)	0.78861 (15)	−0.07384 (7)	0.0455 (4)
C11	0.28495 (19)	0.85679 (16)	−0.12630 (8)	0.0494 (4)
C12	0.39806 (18)	0.75276 (14)	−0.12394 (7)	0.0464 (4)
C13	0.3355 (2)	0.62767 (16)	−0.10734 (9)	0.0540 (5)
C14	0.5728 (2)	0.55895 (16)	−0.07821 (8)	0.0541 (4)
C15	0.62175 (19)	0.67960 (15)	−0.06576 (8)	0.0503 (4)
C16	0.7656 (2)	0.6973 (2)	−0.05198 (9)	0.0659 (5)
H16	0.8007	0.7778	−0.0451	0.079*
C17	0.8591 (2)	0.5977 (2)	−0.04821 (10)	0.0802 (7)
H17	0.9559	0.6109	−0.0386	0.096*
C18	0.8067 (3)	0.4787 (2)	−0.05896 (10)	0.0804 (7)
H18	0.8685	0.4111	−0.0558	0.097*
H10	0.5703 (17)	0.8589 (16)	−0.0883 (7)	0.045 (4)*
H11	0.3340 (17)	0.9362 (16)	−0.1275 (7)	0.047 (4)*
H13A	0.268 (2)	0.5981 (18)	−0.1418 (9)	0.064 (5)*
H13B	0.291 (2)	0.6358 (19)	−0.0683 (10)	0.071 (6)*
C19	0.6654 (3)	0.45911 (19)	−0.07413 (9)	0.0686 (6)
H19	0.6311	0.3786	−0.0817	0.082*
C20	0.4500 (2)	0.74304 (16)	−0.18581 (8)	0.0537 (4)
C21	0.5548 (3)	0.8502 (2)	−0.26125 (11)	0.0918 (8)
H21A	0.5970	0.9297	−0.2676	0.138*
H21B	0.4742	0.8378	−0.2917	0.138*
H21C	0.6227	0.7852	−0.2646	0.138*
C22	0.16930 (19)	0.85119 (15)	−0.17946 (8)	0.0520 (4)
C23	0.0536 (2)	0.77419 (19)	−0.18095 (9)	0.0651 (5)
H23	0.0416	0.7260	−0.1468	0.078*
C24	−0.0450 (2)	0.7678 (2)	−0.23264 (10)	0.0728 (6)
H24	−0.1227	0.7151	−0.2326	0.087*
C25	−0.0313 (2)	0.8371 (2)	−0.28415 (9)	0.0672 (6)
C26	0.0823 (2)	0.9161 (2)	−0.28170 (9)	0.0721 (6)
H26	0.0928	0.9656	−0.3156	0.087*
C27	0.1816 (2)	0.92392 (19)	−0.23030 (9)	0.0642 (5)
H27	0.2574	0.9787	−0.2299	0.077*
C28	−0.1372 (3)	0.8274 (3)	−0.34122 (10)	0.0941 (8)
H28A	−0.2096	0.7686	−0.3345	0.141*
H28B	−0.0901	0.7998	−0.3749	0.141*
H28C	−0.1793	0.9077	−0.3506	0.141*

	U11	U22	U33	U12	U13	U23
O1	0.0720 (9)	0.0549 (7)	0.0397 (7)	−0.0028 (6)	−0.0132 (6)	−0.0050 (5)
O2	0.0612 (9)	0.0693 (9)	0.0601 (8)	−0.0020 (7)	−0.0184 (6)	−0.0081 (6)
O3	0.0575 (7)	0.0596 (7)	0.0412 (7)	0.0072 (6)	−0.0121 (5)	−0.0049 (5)
O4	0.0763 (9)	0.0365 (6)	0.0798 (9)	−0.0020 (6)	−0.0069 (7)	0.0053 (6)
O5	0.1751 (17)	0.0535 (8)	0.0456 (8)	−0.0130 (9)	0.0101 (9)	−0.0111 (6)
O6	0.0880 (10)	0.0519 (7)	0.0548 (8)	−0.0085 (6)	0.0122 (7)	−0.0012 (6)
C1	0.0694 (13)	0.0548 (10)	0.0540 (11)	0.0050 (9)	−0.0023 (9)	0.0028 (8)
C2	0.0788 (14)	0.0683 (13)	0.0671 (14)	0.0075 (11)	0.0134 (11)	0.0081 (10)
C3	0.0958 (18)	0.0695 (13)	0.0567 (13)	0.0042 (12)	0.0178 (12)	0.0050 (10)
C4	0.0954 (16)	0.0571 (11)	0.0405 (10)	−0.0036 (10)	−0.0023 (10)	0.0018 (8)
C5	0.0676 (12)	0.0365 (8)	0.0457 (10)	−0.0007 (7)	−0.0058 (8)	0.0022 (7)
C6	0.0665 (12)	0.0345 (8)	0.0431 (9)	0.0025 (7)	−0.0050 (8)	0.0012 (7)
C7	0.0594 (11)	0.0349 (8)	0.0412 (9)	0.0007 (7)	−0.0126 (7)	−0.0017 (6)
C8	0.0588 (11)	0.0330 (8)	0.0399 (9)	−0.0007 (7)	−0.0102 (7)	−0.0010 (6)
C9	0.0630 (12)	0.0366 (8)	0.0469 (10)	−0.0014 (8)	−0.0142 (8)	−0.0018 (7)
C10	0.0539 (10)	0.0362 (8)	0.0425 (9)	−0.0029 (7)	−0.0086 (7)	0.0007 (7)
C11	0.0598 (11)	0.0411 (9)	0.0430 (10)	0.0002 (8)	−0.0106 (8)	−0.0016 (7)
C12	0.0576 (10)	0.0360 (8)	0.0412 (9)	−0.0012 (7)	−0.0100 (7)	−0.0012 (7)
C13	0.0647 (12)	0.0393 (9)	0.0538 (11)	−0.0053 (8)	−0.0084 (9)	−0.0004 (8)
C14	0.0725 (13)	0.0435 (9)	0.0442 (10)	0.0049 (8)	−0.0008 (8)	0.0067 (7)
C15	0.0607 (11)	0.0461 (9)	0.0410 (9)	0.0062 (8)	−0.0054 (8)	0.0020 (7)
C16	0.0631 (12)	0.0650 (12)	0.0650 (13)	0.0057 (10)	−0.0097 (10)	−0.0008 (10)
C17	0.0667 (14)	0.0942 (18)	0.0759 (15)	0.0222 (12)	−0.0054 (11)	0.0034 (13)
C18	0.0985 (19)	0.0750 (15)	0.0663 (14)	0.0377 (13)	0.0046 (12)	0.0058 (11)
C19	0.0949 (17)	0.0496 (10)	0.0591 (12)	0.0166 (10)	0.0015 (11)	0.0074 (9)
C20	0.0721 (12)	0.0403 (9)	0.0441 (10)	0.0045 (8)	−0.0102 (8)	−0.0002 (7)
C21	0.137 (2)	0.0781 (16)	0.0653 (15)	−0.0017 (14)	0.0319 (14)	0.0077 (11)
C22	0.0636 (11)	0.0445 (9)	0.0426 (9)	0.0068 (8)	−0.0136 (8)	−0.0022 (7)
C23	0.0680 (12)	0.0648 (12)	0.0562 (12)	−0.0028 (10)	−0.0167 (9)	0.0075 (9)
C24	0.0696 (13)	0.0672 (13)	0.0726 (14)	0.0010 (10)	−0.0258 (11)	−0.0026 (11)
C25	0.0730 (13)	0.0730 (13)	0.0491 (11)	0.0267 (11)	−0.0169 (9)	−0.0156 (10)
C26	0.0854 (15)	0.0824 (14)	0.0443 (11)	0.0201 (12)	−0.0078 (10)	0.0087 (10)
C27	0.0725 (13)	0.0611 (11)	0.0541 (11)	0.0063 (9)	−0.0100 (9)	0.0081 (9)
C28	0.0876 (16)	0.120 (2)	0.0632 (14)	0.0365 (15)	−0.0328 (12)	−0.0224 (13)

O1—C5	1.373 (2)	C12—C13	1.530 (2)
O1—C9	1.385 (2)	C13—H13A	0.98 (2)
O2—C9	1.197 (2)	C13—H13B	1.01 (2)
O3—C7	1.3473 (19)	C14—C19	1.382 (3)
O3—C11	1.444 (2)	C14—C15	1.389 (2)
O4—C14	1.358 (2)	C15—C16	1.378 (3)
O4—C13	1.412 (2)	C16—C17	1.386 (3)
O5—C20	1.186 (2)	C16—H16	0.9300
O6—C20	1.318 (2)	C17—C18	1.378 (3)
O6—C21	1.437 (2)	C17—H17	0.9300
C1—C2	1.366 (3)	C18—C19	1.360 (3)
C1—C6	1.392 (3)	C18—H18	0.9300
C1—H1	0.9300	C19—H19	0.9300
C2—C3	1.387 (3)	C21—H21A	0.9600
C2—H2	0.9300	C21—H21B	0.9600
C3—C4	1.362 (3)	C21—H21C	0.9600
C3—H3	0.9300	C22—C23	1.374 (3)
C4—C5	1.381 (3)	C22—C27	1.379 (3)
C4—H4	0.9300	C23—C24	1.379 (3)
C5—C6	1.382 (2)	C23—H23	0.9300
C6—C7	1.437 (2)	C24—C25	1.374 (3)
C7—C8	1.352 (2)	C24—H24	0.9300
C8—C9	1.445 (2)	C25—C26	1.369 (3)
C8—C10	1.518 (2)	C25—C28	1.508 (3)
C10—C15	1.518 (2)	C26—C27	1.379 (3)
C10—C12	1.537 (2)	C26—H26	0.9300
C10—H10	0.972 (17)	C27—H27	0.9300
C11—C22	1.500 (2)	C28—H28A	0.9600
C11—C12	1.546 (2)	C28—H28B	0.9600
C11—H11	0.973 (17)	C28—H28C	0.9600
C12—C20	1.509 (3)
C5—O1—C9	122.17 (13)	C12—C13—H13B	110.3 (12)
C7—O3—C11	114.68 (13)	H13A—C13—H13B	112.1 (16)
C14—O4—C13	118.86 (13)	O4—C14—C19	115.14 (17)
C20—O6—C21	116.42 (16)	O4—C14—C15	123.98 (15)
C2—C1—C6	120.83 (19)	C19—C14—C15	120.83 (19)
C2—C1—H1	119.6	C16—C15—C14	118.07 (16)
C6—C1—H1	119.6	C16—C15—C10	121.77 (16)
C1—C2—C3	119.5 (2)	C14—C15—C10	119.87 (16)
C1—C2—H2	120.2	C15—C16—C17	121.3 (2)
C3—C2—H2	120.2	C15—C16—H16	119.3
C4—C3—C2	121.0 (2)	C17—C16—H16	119.3
C4—C3—H3	119.5	C18—C17—C16	119.1 (2)
C2—C3—H3	119.5	C18—C17—H17	120.4
C3—C4—C5	119.05 (19)	C16—C17—H17	120.4
C3—C4—H4	120.5	C19—C18—C17	120.7 (2)
C5—C4—H4	120.5	C19—C18—H18	119.7
O1—C5—C4	117.78 (16)	C17—C18—H18	119.7
O1—C5—C6	120.81 (16)	C18—C19—C14	120.0 (2)
C4—C5—C6	121.39 (19)	C18—C19—H19	120.0
C5—C6—C1	118.25 (17)	C14—C19—H19	120.0
C5—C6—C7	117.22 (17)	O5—C20—O6	123.41 (18)
C1—C6—C7	124.53 (16)	O5—C20—C12	124.40 (17)
O3—C7—C8	123.92 (16)	O6—C20—C12	112.17 (14)
O3—C7—C6	113.50 (15)	O6—C21—H21A	109.5
C8—C7—C6	122.57 (15)	O6—C21—H21B	109.5
C7—C8—C9	118.14 (16)	H21A—C21—H21B	109.5
C7—C8—C10	122.53 (14)	O6—C21—H21C	109.5
C9—C8—C10	119.16 (15)	H21A—C21—H21C	109.5
O2—C9—O1	115.95 (15)	H21B—C21—H21C	109.5
O2—C9—C8	126.01 (18)	C23—C22—C27	118.11 (16)
O1—C9—C8	118.02 (16)	C23—C22—C11	123.31 (16)
C8—C10—C15	116.16 (13)	C27—C22—C11	118.55 (17)
C8—C10—C12	108.09 (14)	C22—C23—C24	120.59 (19)
C15—C10—C12	107.70 (13)	C22—C23—H23	119.7
C8—C10—H10	109.0 (9)	C24—C23—H23	119.7
C15—C10—H10	106.9 (9)	C25—C24—C23	121.6 (2)
C12—C10—H10	108.7 (10)	C25—C24—H24	119.2
O3—C11—C22	108.59 (15)	C23—C24—H24	119.2
O3—C11—C12	108.18 (13)	C26—C25—C24	117.38 (18)
C22—C11—C12	115.84 (14)	C26—C25—C28	121.1 (2)
O3—C11—H11	108.1 (10)	C24—C25—C28	121.6 (2)
C22—C11—H11	108.7 (10)	C25—C26—C27	121.7 (2)
C12—C11—H11	107.2 (10)	C25—C26—H26	119.2
C20—C12—C13	109.72 (14)	C27—C26—H26	119.2
C20—C12—C10	111.07 (15)	C26—C27—C22	120.6 (2)
C13—C12—C10	109.11 (13)	C26—C27—H27	119.7
C20—C12—C11	109.12 (13)	C22—C27—H27	119.7
C13—C12—C11	110.36 (15)	C25—C28—H28A	109.5
C10—C12—C11	107.42 (13)	C25—C28—H28B	109.5
O4—C13—C12	114.18 (16)	H28A—C28—H28B	109.5
O4—C13—H13A	104.0 (11)	C25—C28—H28C	109.5
C12—C13—H13A	109.6 (11)	H28A—C28—H28C	109.5
O4—C13—H13B	106.5 (12)	H28B—C28—H28C	109.5
C6—C1—C2—C3	−0.2 (3)	O3—C11—C12—C10	−68.00 (17)
C1—C2—C3—C4	−0.2 (3)	C22—C11—C12—C10	169.86 (15)
C2—C3—C4—C5	0.4 (3)	C14—O4—C13—C12	26.9 (2)
C9—O1—C5—C4	−179.86 (15)	C20—C12—C13—O4	66.43 (19)
C9—O1—C5—C6	−1.3 (2)	C10—C12—C13—O4	−55.5 (2)
C3—C4—C5—O1	178.43 (17)	C11—C12—C13—O4	−173.29 (14)
C3—C4—C5—C6	−0.2 (3)	C13—O4—C14—C19	−175.30 (17)
O1—C5—C6—C1	−178.79 (15)	C13—O4—C14—C15	1.9 (3)
C4—C5—C6—C1	−0.2 (2)	O4—C14—C15—C16	−174.18 (17)
O1—C5—C6—C7	2.1 (2)	C19—C14—C15—C16	2.9 (3)
C4—C5—C6—C7	−179.32 (16)	O4—C14—C15—C10	−0.3 (3)
C2—C1—C6—C5	0.4 (3)	C19—C14—C15—C10	176.75 (16)
C2—C1—C6—C7	179.41 (17)	C8—C10—C15—C16	−93.5 (2)
C11—O3—C7—C8	−15.2 (2)	C12—C10—C15—C16	145.19 (17)
C11—O3—C7—C6	166.09 (13)	C8—C10—C15—C14	92.91 (19)
C5—C6—C7—O3	−176.76 (13)	C12—C10—C15—C14	−28.4 (2)
C1—C6—C7—O3	4.2 (2)	C14—C15—C16—C17	−2.5 (3)
C5—C6—C7—C8	4.5 (2)	C10—C15—C16—C17	−176.20 (18)
C1—C6—C7—C8	−174.56 (16)	C15—C16—C17—C18	0.5 (3)
O3—C7—C8—C9	170.02 (14)	C16—C17—C18—C19	1.1 (3)
C6—C7—C8—C9	−11.3 (2)	C17—C18—C19—C14	−0.7 (3)
O3—C7—C8—C10	−5.1 (2)	O4—C14—C19—C18	175.98 (18)
C6—C7—C8—C10	173.51 (14)	C15—C14—C19—C18	−1.4 (3)
C5—O1—C9—O2	172.88 (14)	C21—O6—C20—O5	2.7 (3)
C5—O1—C9—C8	−5.7 (2)	C21—O6—C20—C12	−175.78 (17)
C7—C8—C9—O2	−166.65 (16)	C13—C12—C20—O5	4.2 (3)
C10—C8—C9—O2	8.7 (2)	C10—C12—C20—O5	124.9 (2)
C7—C8—C9—O1	11.8 (2)	C11—C12—C20—O5	−116.8 (2)
C10—C8—C9—O1	−172.92 (13)	C13—C12—C20—O6	−177.29 (14)
C7—C8—C10—C15	−134.14 (16)	C10—C12—C20—O6	−56.57 (18)
C9—C8—C10—C15	50.8 (2)	C11—C12—C20—O6	61.68 (19)
C7—C8—C10—C12	−13.0 (2)	O3—C11—C22—C23	−40.9 (2)
C9—C8—C10—C12	171.88 (13)	C12—C11—C22—C23	81.0 (2)
C7—O3—C11—C22	177.67 (13)	O3—C11—C22—C27	141.21 (17)
C7—O3—C11—C12	51.19 (17)	C12—C11—C22—C27	−96.9 (2)
C8—C10—C12—C20	166.11 (12)	C27—C22—C23—C24	1.8 (3)
C15—C10—C12—C20	−67.66 (17)	C11—C22—C23—C24	−176.10 (18)
C8—C10—C12—C13	−72.81 (17)	C22—C23—C24—C25	0.1 (3)
C15—C10—C12—C13	53.43 (19)	C23—C24—C25—C26	−1.8 (3)
C8—C10—C12—C11	46.84 (17)	C23—C24—C25—C28	178.4 (2)
C15—C10—C12—C11	173.07 (14)	C24—C25—C26—C27	1.6 (3)
O3—C11—C12—C20	171.49 (13)	C28—C25—C26—C27	−178.60 (19)
C22—C11—C12—C20	49.4 (2)	C25—C26—C27—C22	0.3 (3)
O3—C11—C12—C13	50.85 (17)	C23—C22—C27—C26	−2.0 (3)
C22—C11—C12—C13	−71.3 (2)	C11—C22—C27—C26	175.98 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O5i	0.93	2.35	3.209 (2)	153
C21—H21A···O5ii	0.96	2.43	3.285 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O5i	0.93	2.35	3.209 (2)	153
C21—H21A⋯O5ii	0.96	2.43	3.285 (3)	148

Symmetry codes: (i) ; (ii) .