Dimethyl 1,8-bis-(4-methyl-phen-yl)-11-oxatri-cyclo-[6.2.1.0(2,7)]undeca-2,4,6,9-tetra-ene-9,10-di-carboxyl-ate.

The title compound, C28H24O5, consists of a fused tricyclic system containing two five-membered rings and one six-membered ring. The five-membered rings both exhibit an envelope conformation with the O atom at the flap, whereas the six-membered ring adopts a boat conformation. The dihedral angle between the 4-methyl-phenyl rings at the 1,8-positions is 76.4 (1)°. In the crystal, mol-ecules are stacked in columns along the a axis through C-H⋯O inter-actions.

Related literature

For background to Diels–Alder reactions, see: Denmark & Thorarensen (1996 ▶). For related structures, see: Bailey et al. (1995 ▶); Balakrishnan et al. (2013 ▶); Takahashi et al. (2003 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C28H24O5

M = 440.47

Monoclinic,

a = 8.9018 (4) Å

b = 25.6357 (8) Å

c = 11.0961 (4) Å

β = 113.369 (1)°

V = 2324.46 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.975, T max = 0.983

29434 measured reflections

6904 independent reflections

4338 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.170

S = 1.03

6904 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013305/is5270sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013305/is5270Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013305/is5270Isup3.cml

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

C28H24O5	Z = 4
Mr = 440.47	F(000) = 928
Monoclinic, P21/c	Dx = 1.259 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.9018 (4) Å	θ = 2.2–30.2°
b = 25.6357 (8) Å	µ = 0.09 mm−1
c = 11.0961 (4) Å	T = 293 K
β = 113.369 (1)°	Black, colourless
V = 2324.46 (15) Å3	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	6904 independent reflections
Radiation source: fine-focus sealed tube	4338 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω and φ scan	θmax = 30.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.975, Tmax = 0.983	k = −36→34
29434 measured reflections	l = −15→15

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.170	w = 1/[σ2(Fo2) + (0.0787P)2 + 0.4566P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
6904 reflections	Δρmax = 0.30 e Å−3
299 parameters	Δρmin = −0.17 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: 0.0071 (14)

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
C8	0.77122 (19)	0.06795 (6)	0.26149 (15)	0.0371 (3)
C7	0.8610 (2)	0.10788 (6)	0.36867 (16)	0.0398 (3)
C6	0.9676 (2)	0.10415 (7)	0.49831 (16)	0.0465 (4)
H6	0.9919	0.0721	0.5411	0.056*
C5	1.0378 (2)	0.15018 (8)	0.56286 (18)	0.0537 (5)
H5	1.1099	0.1488	0.6506	0.064*
C4	1.0032 (2)	0.19756 (8)	0.5002 (2)	0.0549 (5)
H4	1.0505	0.2277	0.5465	0.066*
C3	0.8982 (2)	0.20119 (7)	0.36820 (18)	0.0479 (4)
H3	0.8759	0.2332	0.3252	0.057*
C2	0.82902 (19)	0.15609 (6)	0.30388 (16)	0.0391 (3)
C1	0.71914 (19)	0.14347 (6)	0.15944 (15)	0.0380 (3)
C16	0.60917 (19)	0.18477 (6)	0.07505 (16)	0.0409 (4)
C22	0.6743 (2)	0.22872 (7)	0.0416 (2)	0.0570 (5)
H22	0.7873	0.2329	0.0737	0.068*
C21	0.5732 (3)	0.26660 (8)	−0.0392 (2)	0.0621 (5)
H21	0.6193	0.2957	−0.0613	0.075*
C19	0.4047 (2)	0.26197 (8)	−0.08750 (18)	0.0559 (5)
C20	0.2962 (3)	0.30280 (11)	−0.1783 (2)	0.0864 (8)
H20A	0.1836	0.2934	−0.2025	0.130*
H20C	0.3191	0.3051	−0.2557	0.130*
H20B	0.3169	0.3360	−0.1345	0.130*
C18	0.3410 (2)	0.21909 (8)	−0.0500 (2)	0.0580 (5)
H18	0.2281	0.2158	−0.0792	0.070*
C17	0.4401 (2)	0.18069 (7)	0.03012 (18)	0.0499 (4)
H17	0.3935	0.1521	0.0539	0.060*
C9	0.7112 (2)	0.01647 (6)	0.28848 (16)	0.0420 (4)
C10	0.6997 (2)	0.00459 (8)	0.40519 (19)	0.0574 (5)
H10	0.7347	0.0286	0.4735	0.069*
C11	0.6362 (3)	−0.04307 (10)	0.4220 (2)	0.0726 (6)
H11	0.6310	−0.0506	0.5022	0.087*
C12	0.5807 (2)	−0.07938 (8)	0.3224 (2)	0.0665 (6)
C13	0.5158 (3)	−0.13196 (10)	0.3413 (3)	0.1046 (11)
H13A	0.5200	−0.1343	0.4289	0.157*
H13B	0.5816	−0.1591	0.3276	0.157*
H13C	0.4046	−0.1358	0.2794	0.157*
C14	0.5881 (3)	−0.06670 (8)	0.2050 (2)	0.0650 (5)
H14	0.5488	−0.0902	0.1356	0.078*
C15	0.6529 (2)	−0.01967 (7)	0.1876 (2)	0.0554 (5)
H15	0.6574	−0.0122	0.1071	0.066*
C26	0.87077 (18)	0.06868 (6)	0.17415 (14)	0.0363 (3)
C27	1.0114 (2)	0.03366 (6)	0.19642 (16)	0.0407 (4)
C28	1.2486 (2)	0.02100 (9)	0.1527 (2)	0.0694 (6)
H28A	1.2993	0.0355	0.0984	0.104*
H28B	1.2249	−0.0152	0.1315	0.104*
H28C	1.3214	0.0243	0.2434	0.104*
C23	0.83616 (18)	0.11356 (6)	0.10885 (14)	0.0359 (3)
C24	0.91045 (19)	0.13555 (6)	0.02149 (15)	0.0380 (3)
C25	0.9345 (4)	0.12516 (10)	−0.1798 (2)	0.0781 (7)
H25A	0.8917	0.1039	−0.2573	0.117*
H25B	1.0511	0.1209	−0.1384	0.117*
H25C	0.9091	0.1611	−0.2033	0.117*
O1	0.63095 (13)	0.09913 (4)	0.17856 (11)	0.0401 (3)
O4	1.0475 (2)	−0.00215 (6)	0.27114 (16)	0.0750 (5)
O5	1.09867 (17)	0.04857 (6)	0.13005 (15)	0.0648 (4)
O2	0.99992 (17)	0.17240 (5)	0.04755 (13)	0.0595 (4)
O3	0.86178 (17)	0.10946 (5)	−0.08975 (12)	0.0566 (4)

	U11	U22	U33	U12	U13	U23
C8	0.0394 (8)	0.0369 (8)	0.0392 (8)	0.0058 (6)	0.0199 (7)	0.0033 (6)
C7	0.0438 (8)	0.0403 (8)	0.0424 (8)	0.0035 (7)	0.0246 (7)	−0.0017 (6)
C6	0.0512 (10)	0.0517 (10)	0.0426 (9)	0.0039 (8)	0.0250 (8)	0.0009 (7)
C5	0.0534 (10)	0.0666 (12)	0.0443 (9)	−0.0025 (9)	0.0227 (8)	−0.0100 (9)
C4	0.0575 (11)	0.0533 (11)	0.0607 (11)	−0.0079 (9)	0.0307 (9)	−0.0196 (9)
C3	0.0523 (10)	0.0391 (8)	0.0613 (11)	0.0028 (7)	0.0321 (9)	−0.0042 (8)
C2	0.0403 (8)	0.0382 (8)	0.0464 (8)	0.0055 (6)	0.0252 (7)	−0.0011 (6)
C1	0.0376 (8)	0.0360 (8)	0.0465 (8)	0.0027 (6)	0.0230 (7)	0.0026 (6)
C16	0.0398 (8)	0.0394 (8)	0.0484 (9)	0.0075 (6)	0.0228 (7)	0.0041 (7)
C22	0.0434 (9)	0.0532 (11)	0.0804 (13)	0.0116 (8)	0.0308 (9)	0.0201 (10)
C21	0.0627 (12)	0.0557 (11)	0.0822 (14)	0.0194 (9)	0.0438 (11)	0.0275 (10)
C19	0.0558 (11)	0.0655 (12)	0.0493 (10)	0.0225 (9)	0.0239 (9)	0.0141 (9)
C20	0.0793 (16)	0.1036 (19)	0.0741 (15)	0.0402 (15)	0.0280 (13)	0.0407 (14)
C18	0.0397 (9)	0.0655 (12)	0.0632 (12)	0.0108 (9)	0.0146 (9)	0.0046 (10)
C17	0.0450 (9)	0.0467 (9)	0.0602 (11)	0.0031 (7)	0.0230 (8)	0.0026 (8)
C9	0.0424 (8)	0.0381 (8)	0.0486 (9)	0.0040 (7)	0.0214 (7)	0.0058 (7)
C10	0.0621 (12)	0.0612 (11)	0.0511 (10)	−0.0081 (9)	0.0248 (9)	0.0072 (9)
C11	0.0665 (13)	0.0842 (16)	0.0634 (13)	−0.0132 (12)	0.0219 (11)	0.0292 (12)
C12	0.0456 (10)	0.0532 (11)	0.0907 (16)	−0.0019 (9)	0.0164 (10)	0.0258 (11)
C13	0.0777 (17)	0.0762 (16)	0.138 (3)	−0.0227 (14)	0.0192 (17)	0.0424 (17)
C14	0.0620 (12)	0.0479 (10)	0.0832 (15)	−0.0097 (9)	0.0268 (11)	−0.0047 (10)
C15	0.0648 (12)	0.0475 (10)	0.0594 (11)	−0.0070 (9)	0.0306 (10)	−0.0042 (8)
C26	0.0387 (8)	0.0355 (7)	0.0377 (7)	0.0030 (6)	0.0183 (6)	−0.0014 (6)
C27	0.0432 (9)	0.0404 (8)	0.0387 (8)	0.0068 (7)	0.0165 (7)	−0.0037 (7)
C28	0.0493 (11)	0.0777 (14)	0.0899 (16)	0.0173 (10)	0.0368 (11)	−0.0038 (12)
C23	0.0345 (7)	0.0376 (8)	0.0376 (8)	0.0012 (6)	0.0163 (6)	−0.0017 (6)
C24	0.0364 (8)	0.0394 (8)	0.0402 (8)	0.0020 (6)	0.0171 (6)	0.0003 (6)
C25	0.1121 (19)	0.0845 (15)	0.0655 (13)	−0.0214 (14)	0.0648 (14)	−0.0108 (12)
O1	0.0375 (6)	0.0379 (6)	0.0494 (6)	0.0030 (4)	0.0218 (5)	0.0054 (5)
O4	0.0805 (10)	0.0741 (9)	0.0850 (10)	0.0389 (8)	0.0484 (9)	0.0360 (8)
O5	0.0582 (8)	0.0647 (8)	0.0903 (10)	0.0230 (7)	0.0495 (8)	0.0212 (7)
O2	0.0621 (8)	0.0579 (8)	0.0655 (8)	−0.0220 (7)	0.0329 (7)	−0.0116 (6)
O3	0.0732 (9)	0.0604 (8)	0.0466 (7)	−0.0216 (7)	0.0349 (6)	−0.0126 (6)

C8—O1	1.4607 (18)	C17—H17	0.9300
C8—C9	1.498 (2)	C9—C10	1.373 (2)
C8—C7	1.532 (2)	C9—C15	1.386 (3)
C8—C26	1.551 (2)	C10—C11	1.390 (3)
C7—C6	1.377 (2)	C10—H10	0.9300
C7—C2	1.401 (2)	C11—C12	1.378 (3)
C6—C5	1.393 (3)	C11—H11	0.9300
C6—H6	0.9300	C12—C14	1.369 (3)
C5—C4	1.372 (3)	C12—C13	1.514 (3)
C5—H5	0.9300	C13—H13A	0.9600
C4—C3	1.393 (3)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C3—C2	1.370 (2)	C14—C15	1.383 (3)
C3—H3	0.9300	C14—H14	0.9300
C2—C1	1.545 (2)	C15—H15	0.9300
C1—O1	1.4441 (18)	C26—C23	1.329 (2)
C1—C16	1.493 (2)	C26—C27	1.480 (2)
C1—C23	1.566 (2)	C27—O4	1.192 (2)
C16—C22	1.384 (2)	C27—O5	1.321 (2)
C16—C17	1.389 (2)	C28—O5	1.441 (2)
C22—C21	1.384 (3)	C28—H28A	0.9600
C22—H22	0.9300	C28—H28B	0.9600
C21—C19	1.383 (3)	C28—H28C	0.9600
C21—H21	0.9300	C23—C24	1.484 (2)
C19—C18	1.375 (3)	C24—O2	1.1948 (19)
C19—C20	1.507 (3)	C24—O3	1.3170 (19)
C20—H20A	0.9600	C25—O3	1.447 (2)
C20—H20C	0.9600	C25—H25A	0.9600
C20—H20B	0.9600	C25—H25B	0.9600
C18—C17	1.384 (3)	C25—H25C	0.9600
C18—H18	0.9300
O1—C8—C9	108.93 (12)	C16—C17—H17	120.0
O1—C8—C7	100.11 (11)	C10—C9—C15	118.01 (16)
C9—C8—C7	123.44 (13)	C10—C9—C8	123.36 (16)
O1—C8—C26	99.05 (11)	C15—C9—C8	118.46 (15)
C9—C8—C26	118.25 (12)	C9—C10—C11	120.5 (2)
C7—C8—C26	103.04 (12)	C9—C10—H10	119.7
C6—C7—C2	120.85 (15)	C11—C10—H10	119.7
C6—C7—C8	134.08 (15)	C12—C11—C10	121.4 (2)
C2—C7—C8	104.71 (13)	C12—C11—H11	119.3
C7—C6—C5	117.45 (17)	C10—C11—H11	119.3
C7—C6—H6	121.3	C14—C12—C11	117.75 (18)
C5—C6—H6	121.3	C14—C12—C13	120.6 (2)
C4—C5—C6	121.63 (18)	C11—C12—C13	121.7 (2)
C4—C5—H5	119.2	C12—C13—H13A	109.5
C6—C5—H5	119.2	C12—C13—H13B	109.5
C5—C4—C3	120.92 (17)	H13A—C13—H13B	109.5
C5—C4—H4	119.5	C12—C13—H13C	109.5
C3—C4—H4	119.5	H13A—C13—H13C	109.5
C2—C3—C4	117.82 (17)	H13B—C13—H13C	109.5
C2—C3—H3	121.1	C12—C14—C15	121.3 (2)
C4—C3—H3	121.1	C12—C14—H14	119.3
C3—C2—C7	121.29 (16)	C15—C14—H14	119.3
C3—C2—C1	133.32 (15)	C14—C15—C9	120.90 (19)
C7—C2—C1	105.29 (13)	C14—C15—H15	119.6
O1—C1—C16	113.01 (12)	C9—C15—H15	119.6
O1—C1—C2	99.77 (12)	C23—C26—C27	127.89 (14)
C16—C1—C2	119.34 (13)	C23—C26—C8	106.55 (12)
O1—C1—C23	98.34 (11)	C27—C26—C8	122.93 (13)
C16—C1—C23	119.10 (13)	O4—C27—O5	123.69 (15)
C2—C1—C23	103.71 (12)	O4—C27—C26	124.04 (16)
C22—C16—C17	118.35 (16)	O5—C27—C26	112.14 (14)
C22—C16—C1	120.35 (15)	O5—C28—H28A	109.5
C17—C16—C1	121.29 (15)	O5—C28—H28B	109.5
C16—C22—C21	120.69 (18)	H28A—C28—H28B	109.5
C16—C22—H22	119.7	O5—C28—H28C	109.5
C21—C22—H22	119.7	H28A—C28—H28C	109.5
C19—C21—C22	121.19 (18)	H28B—C28—H28C	109.5
C19—C21—H21	119.4	C26—C23—C24	128.15 (14)
C22—C21—H21	119.4	C26—C23—C1	105.77 (12)
C18—C19—C21	117.71 (17)	C24—C23—C1	125.47 (13)
C18—C19—C20	121.7 (2)	O2—C24—O3	124.63 (15)
C21—C19—C20	120.6 (2)	O2—C24—C23	124.68 (14)
C19—C20—H20A	109.5	O3—C24—C23	110.67 (13)
C19—C20—H20C	109.5	O3—C25—H25A	109.5
H20A—C20—H20C	109.5	O3—C25—H25B	109.5
C19—C20—H20B	109.5	H25A—C25—H25B	109.5
H20A—C20—H20B	109.5	O3—C25—H25C	109.5
H20C—C20—H20B	109.5	H25A—C25—H25C	109.5
C19—C18—C17	121.92 (18)	H25B—C25—H25C	109.5
C19—C18—H18	119.0	C1—O1—C8	98.32 (11)
C17—C18—H18	119.0	C27—O5—C28	117.97 (15)
C18—C17—C16	120.06 (17)	C24—O3—C25	115.78 (15)
C18—C17—H17	120.0
O1—C8—C7—C6	154.22 (17)	C15—C9—C10—C11	2.0 (3)
C9—C8—C7—C6	33.4 (3)	C8—C9—C10—C11	177.15 (18)
C26—C8—C7—C6	−103.93 (19)	C9—C10—C11—C12	−1.0 (3)
O1—C8—C7—C2	−32.90 (14)	C10—C11—C12—C14	−0.9 (3)
C9—C8—C7—C2	−153.74 (14)	C10—C11—C12—C13	178.2 (2)
C26—C8—C7—C2	68.95 (14)	C11—C12—C14—C15	1.7 (3)
C2—C7—C6—C5	2.0 (2)	C13—C12—C14—C15	−177.4 (2)
C8—C7—C6—C5	173.92 (16)	C12—C14—C15—C9	−0.6 (3)
C7—C6—C5—C4	−0.3 (3)	C10—C9—C15—C14	−1.3 (3)
C6—C5—C4—C3	−1.2 (3)	C8—C9—C15—C14	−176.61 (17)
C5—C4—C3—C2	1.0 (3)	O1—C8—C26—C23	30.30 (15)
C4—C3—C2—C7	0.7 (2)	C9—C8—C26—C23	147.58 (14)
C4—C3—C2—C1	−175.06 (16)	C7—C8—C26—C23	−72.38 (15)
C6—C7—C2—C3	−2.2 (2)	O1—C8—C26—C27	−166.84 (13)
C8—C7—C2—C3	−176.24 (14)	C9—C8—C26—C27	−49.6 (2)
C6—C7—C2—C1	174.58 (14)	C7—C8—C26—C27	90.48 (16)
C8—C7—C2—C1	0.54 (15)	C23—C26—C27—O4	168.97 (18)
C3—C2—C1—O1	−151.42 (17)	C8—C26—C27—O4	9.9 (3)
C7—C2—C1—O1	32.37 (14)	C23—C26—C27—O5	−7.1 (2)
C3—C2—C1—C16	−27.9 (2)	C8—C26—C27—O5	−166.12 (14)
C7—C2—C1—C16	155.86 (13)	C27—C26—C23—C24	12.2 (3)
C3—C2—C1—C23	107.43 (19)	C8—C26—C23—C24	173.96 (14)
C7—C2—C1—C23	−68.79 (14)	C27—C26—C23—C1	−159.09 (15)
O1—C1—C16—C22	−176.73 (15)	C8—C26—C23—C1	2.64 (16)
C2—C1—C16—C22	66.5 (2)	O1—C1—C23—C26	−35.12 (15)
C23—C1—C16—C22	−62.1 (2)	C16—C1—C23—C26	−157.38 (14)
O1—C1—C16—C17	4.4 (2)	C2—C1—C23—C26	67.14 (15)
C2—C1—C16—C17	−112.39 (18)	O1—C1—C23—C24	153.27 (14)
C23—C1—C16—C17	119.00 (17)	C16—C1—C23—C24	31.0 (2)
C17—C16—C22—C21	−2.6 (3)	C2—C1—C23—C24	−104.47 (16)
C1—C16—C22—C21	178.46 (18)	C26—C23—C24—O2	−109.2 (2)
C16—C22—C21—C19	0.7 (3)	C1—C23—C24—O2	60.5 (2)
C22—C21—C19—C18	1.6 (3)	C26—C23—C24—O3	72.0 (2)
C22—C21—C19—C20	−178.3 (2)	C1—C23—C24—O3	−118.32 (16)
C21—C19—C18—C17	−1.9 (3)	C16—C1—O1—C8	179.75 (12)
C20—C19—C18—C17	178.0 (2)	C2—C1—O1—C8	−52.41 (12)
C19—C18—C17—C16	0.0 (3)	C23—C1—O1—C8	53.15 (12)
C22—C16—C17—C18	2.3 (3)	C9—C8—O1—C1	−176.06 (12)
C1—C16—C17—C18	−178.81 (16)	C7—C8—O1—C1	53.18 (12)
O1—C8—C9—C10	−102.59 (18)	C26—C8—O1—C1	−51.92 (12)
C7—C8—C9—C10	14.1 (2)	O4—C27—O5—C28	−2.1 (3)
C26—C8—C9—C10	145.51 (17)	C26—C27—O5—C28	173.95 (16)
O1—C8—C9—C15	72.50 (18)	O2—C24—O3—C25	5.0 (3)
C7—C8—C9—C15	−170.83 (15)	C23—C24—O3—C25	−176.13 (17)
C26—C8—C9—C15	−39.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13C···O3i	0.96	2.56	3.461 (3)	157
C28—H28B···O3ii	0.96	2.52	3.478 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13C⋯O3i	0.96	2.56	3.461 (3)	157
C28—H28B⋯O3ii	0.96	2.52	3.478 (3)	173

Symmetry codes: (i) ; (ii) .