Ethyl (6aRS,8RS,12bRS)-6-oxo-8-phenyl-6a,7,8,12b-tetra­hydro-6H-benzo­[b]naphtho­[1,2-d]­pyran-6a-carboxylate

In the title compound, C₂₆H₂₂O₄, the pyran­one ring adopts a twisted boat conformation, while the cyclo­hexane ring is close to an envelope conformation. The dihedral angle between the mean planes of the coumarin and naphthalene systems is 78.8 (1)°. The attached phenyl ring is in an equatorial position with respect to the cyclo­hexane ring.

S1. Comment

The photoinduced reactions of coumarin derivatives have been widely investigated (Lewis & Barancyk, 1989). However, the photoinduced reactions of coumarins with phenylethenes have not been much investigated. In order to extend the scope of photoinduced reactions of coumarin derivatives, we have conducted the photoinduced reaction of 3-ethoxycarbonylcoumarin with 1,1-diphenylethene. It is unexpectedly found that the coumarin ring was annulated in this reaction to give the title compound, (I). An X-ray crystal structure analysis of (I) was undertaken to confirm its novel four-ring structure. The crystal structure is a racemate.

In the title structure (Fig. 1), the pyranone ring adopts a twisted boat conformation, with atoms C1 and C2 deviating by ±0.300 (3) Å and puckering parameters (Cremer & Pople, 1975) Q₂ = 0.445 (3) Å, Q₃ = 0.192 (3) Å, Q_T = 0.484 (3) Å, θ = 66.7 (4)° and ϕ₂ = 151.0 (4)°. The cyclohexane ring is close to an envelope conformation, with atom C1 deviating by -0.358 (2) Å and puckering parameters Q₂ = 0.413 (3) Å, Q₃ = -0.290 (3) Å, Q_T = 0.505 (3) Å, θ = 125.1 (3)° and ϕ₂ = 170.2 (4)°. The dihedral angle between the mean planes through the pyranone and cyclohexane rings is 69.7 (2)°, while these two rings make dihedral angles of 15.9 (2) and 10.2 (1)° with the benzene rings in the coumarin and naphthalene moieties, respectively. The coumarin and naphthalene moieties make a dihedral angle of 78.8 (1)° with one another, corresponding to a synclinical configuration.

The bond lengths and angles within (I) are normal (Allen et al., 1987). Except for the C3—C8 and C12—C17 bonds, all the C—C bond distances in the pyranone and cyclohexane rings are typical Csp³—Csp³ single-bond values. The average C—C bond distances within the benzene and phenyl rings are 1.377 (4), 1.381 (4) and 1.387 (4) Å.

The phenyl-ring substituent attached to the cyclohexane ring moiety at C9 is twisted by 68.1 (2)° with respect to the mean plane of the cyclohexane ring, corresponding to an equatorial position with respect to the cyclohexane ring. The ketone O2 atom deviates by 0.286 (2) Å from the cyclohexane ring. The ethoxycarbonyl group is nearly planar, with atom O3 deviating by 0.261 (2) Å. This plane makes a dihedral angle of 85.4 (3)° to the cyclohexane ring.

In the title structure, an intramolecular C—H···O interaction forms an O4—C24—C1—C2—H2A closed ring. The molecules are stacked into columns nearly along the c axis. One weak intermolecular C—H···O interaction (symmetry code: x, y + 1, z) was also observed which interconnects the molecules into infinite molecular sheets along the b axis. These interactions, as well as van der Waals interactions, stabilize the molecular and packing structure in the crystal.

S2. Experimental

The title compound, (I), was prepared by photolysis of 3-ethoxycarbonylcoumarin (50 mmol) in benzene solution with an excess amount of 1,1-diphenylethylene using light of wavelength longer than 300 nm. Single crystals suitable for X-ray diffraction analysis were recrystallized by slow evaporation from a petroleum ether–ethyl acetate solution.

S3. Refinement

After checking their presence in the difference map, all H atoms were fixed geometrically and allowed to ride on the parent C atoms (C—H = 0.93–0.98 Å).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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, 1990).

Figures

	Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Packing diagram of the structure (I) viewed down the a axis.

Ethyl (6aRS,8RS,12bRS)-6-oxo-8-phenyl-6a,7,8,12b-tetrahydro-6H-benzo[b]- naphtho[1,2-d]pyran-6a-carboxylate

Crystal data

C26H22O4	Z = 2
Mr = 398.44	F(000) = 420
Triclinic, P1	Dx = 1.282 Mg m^−3
Hall symbol: -P 1	Melting point: 435K K
a = 10.5692 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6982 (2) Å	Cell parameters from 4216 reflections
c = 10.7687 (1) Å	θ = 2.0–28.3°
α = 94.848 (1)°	µ = 0.09 mm^−1
β = 99.091 (1)°	T = 293 K
γ = 119.064 (1)°	Slab, colourless
V = 1032.43 (3) Å^3	0.36 × 0.30 × 0.14 mm

Data collection

Siemens SMART CCD area-detector diffractometer	4425 independent reflections
Radiation source: fine-focus sealed tube	2402 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
Detector resolution: 8.33 pixels mm^-1	θmax = 27.0°, θmin = 2.0°
ω scans	h = −12→13
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −12→13
Tmin = 0.970, Tmax = 0.988	l = −13→10
6894 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.075	H-atom parameters constrained
wR(F^2) = 0.209	w = 1/[σ^2(Fo^2) + (0.0916P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.87	(Δ/σ)max < 0.001
4425 reflections	Δρmax = 0.57 e Å^−3
272 parameters	Δρmin = −0.59 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.226 (15)

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 4 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	0.2491 (2)	0.5661 (2)	0.35589 (19)	0.0495 (6)
O2	0.2382 (2)	0.4991 (2)	0.1549 (2)	0.0564 (6)
O3	0.1815 (2)	0.7109 (2)	−0.02682 (18)	0.0513 (6)
O4	0.40941 (19)	0.8018 (2)	0.09736 (17)	0.0441 (5)
C1	0.2103 (3)	0.7073 (3)	0.2001 (2)	0.0302 (6)
C2	0.2992 (3)	0.8420 (3)	0.3095 (2)	0.0318 (6)
H2A	0.4055	0.8795	0.3159	0.038*
C3	0.2661 (3)	0.9592 (3)	0.2788 (2)	0.0345 (6)
C4	0.3750 (3)	1.1048 (3)	0.3189 (3)	0.0462 (7)
H4A	0.4693	1.1284	0.3626	0.055*
C5	0.3482 (4)	1.2150 (3)	0.2964 (3)	0.0600 (9)
H5A	0.4233	1.3117	0.3244	0.072*
C6	0.2092 (4)	1.1812 (4)	0.2320 (3)	0.0637 (10)
H6A	0.1893	1.2552	0.2179	0.076*
C7	0.0986 (4)	1.0369 (3)	0.1880 (3)	0.0501 (8)
H7A	0.0059	1.0150	0.1420	0.060*
C8	0.1243 (3)	0.9240 (3)	0.2116 (2)	0.0341 (6)
C9	−0.0002 (3)	0.7678 (3)	0.1611 (2)	0.0328 (6)
H9A	−0.0318	0.7578	0.0685	0.039*
C10	0.0433 (3)	0.6524 (3)	0.1824 (2)	0.0330 (6)
H10A	−0.0106	0.5725	0.1097	0.040*
H10B	0.0120	0.6142	0.2576	0.040*
C11	0.2344 (3)	0.5839 (3)	0.2323 (3)	0.0381 (6)
C12	0.2392 (3)	0.6569 (3)	0.4504 (3)	0.0431 (7)
C13	0.2054 (4)	0.6027 (4)	0.5602 (3)	0.0589 (9)
H13A	0.1911	0.5112	0.5689	0.071*
C14	0.1935 (4)	0.6867 (4)	0.6560 (3)	0.0697 (11)
H14A	0.1711	0.6520	0.7307	0.084*
C15	0.2144 (4)	0.8210 (4)	0.6426 (3)	0.0692 (10)
H15A	0.2044	0.8763	0.7076	0.083*
C16	0.2504 (3)	0.8754 (4)	0.5323 (3)	0.0516 (8)
H16A	0.2665	0.9677	0.5249	0.062*
C17	0.2626 (3)	0.7929 (3)	0.4334 (2)	0.0363 (6)
C18	−0.1358 (3)	0.7301 (3)	0.2171 (3)	0.0370 (6)
C19	−0.1227 (3)	0.7930 (3)	0.3398 (3)	0.0512 (8)
H19A	−0.0302	0.8654	0.3886	0.061*
C20	−0.2497 (4)	0.7470 (4)	0.3900 (4)	0.0663 (10)
H20A	−0.2408	0.7896	0.4723	0.080*
C21	−0.3848 (4)	0.6414 (4)	0.3204 (4)	0.0657 (10)
H21A	−0.4682	0.6114	0.3548	0.079*
C22	−0.3981 (3)	0.5793 (4)	0.1997 (4)	0.0625 (9)
H22A	−0.4913	0.5070	0.1520	0.075*
C23	−0.2773 (3)	0.6213 (3)	0.1479 (3)	0.0496 (8)
H23A	−0.2890	0.5771	0.0654	0.060*
C24	0.2626 (3)	0.7401 (3)	0.0760 (2)	0.0336 (6)
C25	0.4751 (3)	0.8142 (3)	−0.0124 (3)	0.0483 (7)
H25A	0.4454	0.8654	−0.0695	0.058*
H25C	0.4429	0.7183	−0.0592	0.058*
C26	0.6405 (3)	0.8970 (4)	0.0371 (3)	0.0556 (8)
H26D	0.6879	0.9073	−0.0334	0.083*
H26A	0.6685	0.8452	0.0933	0.083*
H26B	0.6710	0.9916	0.0831	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0673 (14)	0.0514 (13)	0.0489 (12)	0.0381 (11)	0.0267 (10)	0.0254 (9)
O2	0.0760 (15)	0.0453 (13)	0.0673 (14)	0.0396 (11)	0.0343 (12)	0.0144 (10)
O3	0.0493 (12)	0.0657 (14)	0.0307 (11)	0.0221 (10)	0.0130 (9)	0.0081 (9)
O4	0.0377 (10)	0.0609 (13)	0.0366 (10)	0.0221 (9)	0.0235 (8)	0.0147 (8)
C1	0.0323 (12)	0.0304 (13)	0.0304 (13)	0.0148 (10)	0.0159 (10)	0.0093 (9)
C2	0.0296 (12)	0.0340 (14)	0.0288 (13)	0.0118 (10)	0.0128 (10)	0.0081 (10)
C3	0.0420 (14)	0.0295 (13)	0.0296 (13)	0.0130 (11)	0.0186 (11)	0.0081 (9)
C4	0.0511 (17)	0.0319 (15)	0.0438 (16)	0.0091 (12)	0.0211 (13)	0.0078 (11)
C5	0.078 (2)	0.0288 (16)	0.062 (2)	0.0135 (15)	0.0351 (19)	0.0095 (13)
C6	0.102 (3)	0.0413 (19)	0.073 (2)	0.0434 (19)	0.052 (2)	0.0292 (16)
C7	0.0619 (19)	0.0505 (19)	0.0586 (19)	0.0360 (16)	0.0328 (16)	0.0282 (14)
C8	0.0414 (14)	0.0339 (14)	0.0343 (14)	0.0191 (11)	0.0241 (11)	0.0140 (10)
C9	0.0335 (13)	0.0363 (14)	0.0298 (13)	0.0163 (11)	0.0136 (10)	0.0101 (10)
C10	0.0309 (12)	0.0289 (13)	0.0362 (14)	0.0110 (10)	0.0146 (11)	0.0057 (10)
C11	0.0378 (14)	0.0362 (15)	0.0456 (16)	0.0183 (11)	0.0208 (12)	0.0151 (11)
C12	0.0437 (16)	0.0504 (17)	0.0363 (15)	0.0211 (13)	0.0158 (12)	0.0182 (12)
C13	0.065 (2)	0.061 (2)	0.0427 (18)	0.0216 (16)	0.0154 (16)	0.0280 (15)
C14	0.077 (2)	0.079 (3)	0.0317 (17)	0.0193 (19)	0.0206 (16)	0.0229 (16)
C15	0.081 (2)	0.082 (3)	0.0310 (17)	0.030 (2)	0.0232 (17)	0.0048 (15)
C16	0.0597 (19)	0.0542 (19)	0.0311 (15)	0.0208 (14)	0.0147 (13)	0.0050 (12)
C17	0.0336 (13)	0.0416 (15)	0.0283 (13)	0.0133 (11)	0.0108 (11)	0.0102 (10)
C18	0.0370 (14)	0.0416 (15)	0.0426 (15)	0.0238 (12)	0.0175 (12)	0.0171 (11)
C19	0.0479 (17)	0.060 (2)	0.0484 (17)	0.0257 (15)	0.0242 (14)	0.0100 (14)
C20	0.075 (2)	0.080 (3)	0.068 (2)	0.047 (2)	0.044 (2)	0.0241 (18)
C21	0.0479 (19)	0.071 (2)	0.102 (3)	0.0360 (18)	0.048 (2)	0.040 (2)
C22	0.0365 (16)	0.065 (2)	0.087 (3)	0.0231 (15)	0.0232 (17)	0.0210 (18)
C23	0.0370 (15)	0.0479 (18)	0.0607 (19)	0.0180 (13)	0.0147 (14)	0.0108 (14)
C24	0.0368 (13)	0.0314 (13)	0.0347 (14)	0.0158 (11)	0.0178 (12)	0.0080 (10)
C25	0.0563 (18)	0.0527 (18)	0.0443 (16)	0.0263 (14)	0.0348 (14)	0.0150 (12)
C26	0.0479 (17)	0.069 (2)	0.062 (2)	0.0303 (16)	0.0357 (16)	0.0250 (16)

Geometric parameters (Å, º)

O1—C11	1.356 (3)	C10—H10B	0.9700
O1—C12	1.399 (3)	C12—C13	1.382 (4)
O2—C11	1.199 (3)	C12—C17	1.387 (4)
O3—C24	1.200 (3)	C13—C14	1.372 (5)
O4—C24	1.328 (3)	C13—H13A	0.9300
O4—C25	1.447 (3)	C14—C15	1.368 (5)
C1—C11	1.518 (4)	C14—H14A	0.9300
C1—C24	1.530 (3)	C15—C16	1.393 (4)
C1—C10	1.537 (3)	C15—H15A	0.9300
C1—C2	1.548 (3)	C16—C17	1.387 (4)
C2—C3	1.504 (4)	C16—H16A	0.9300
C2—C17	1.513 (3)	C18—C19	1.385 (4)
C2—H2A	0.9800	C18—C23	1.399 (4)
C3—C4	1.388 (4)	C19—C20	1.403 (4)
C3—C8	1.404 (4)	C19—H19A	0.9300
C4—C5	1.372 (4)	C20—C21	1.352 (5)
C4—H4A	0.9300	C20—H20A	0.9300
C5—C6	1.375 (5)	C21—C22	1.363 (5)
C5—H5A	0.9300	C21—H21A	0.9300
C6—C7	1.386 (5)	C22—C23	1.362 (4)
C6—H6A	0.9300	C22—H22A	0.9300
C7—C8	1.396 (4)	C23—H23A	0.9300
C7—H7A	0.9300	C25—C26	1.498 (4)
C8—C9	1.518 (3)	C25—H25A	0.9700
C9—C18	1.527 (3)	C25—H25C	0.9700
C9—C10	1.535 (3)	C26—H26D	0.9600
C9—H9A	0.9800	C26—H26A	0.9600
C10—H10A	0.9700	C26—H26B	0.9600
C11—O1—C12	120.9 (2)	C17—C12—O1	121.3 (2)
C24—O4—C25	117.9 (2)	C14—C13—C12	118.6 (3)
C11—C1—C24	105.24 (18)	C14—C13—H13A	120.7
C11—C1—C10	107.43 (19)	C12—C13—H13A	120.7
C24—C1—C10	112.1 (2)	C15—C14—C13	120.5 (3)
C11—C1—C2	111.0 (2)	C15—C14—H14A	119.7
C24—C1—C2	111.6 (2)	C13—C14—H14A	119.7
C10—C1—C2	109.34 (19)	C14—C15—C16	120.4 (3)
C3—C2—C17	113.8 (2)	C14—C15—H15A	119.8
C3—C2—C1	109.9 (2)	C16—C15—H15A	119.8
C17—C2—C1	108.0 (2)	C17—C16—C15	120.5 (3)
C3—C2—H2A	108.3	C17—C16—H16A	119.8
C17—C2—H2A	108.3	C15—C16—H16A	119.8
C1—C2—H2A	108.3	C12—C17—C16	117.2 (2)
C4—C3—C8	118.8 (3)	C12—C17—C2	118.6 (2)
C4—C3—C2	120.2 (2)	C16—C17—C2	124.2 (3)
C8—C3—C2	121.0 (2)	C19—C18—C23	118.0 (2)
C5—C4—C3	122.1 (3)	C19—C18—C9	121.9 (2)
C5—C4—H4A	118.9	C23—C18—C9	120.0 (2)
C3—C4—H4A	118.9	C18—C19—C20	119.6 (3)
C4—C5—C6	119.4 (3)	C18—C19—H19A	120.2
C4—C5—H5A	120.3	C20—C19—H19A	120.2
C6—C5—H5A	120.3	C21—C20—C19	120.9 (3)
C5—C6—C7	120.0 (3)	C21—C20—H20A	119.6
C5—C6—H6A	120.0	C19—C20—H20A	119.6
C7—C6—H6A	120.0	C20—C21—C22	119.7 (3)
C6—C7—C8	121.0 (3)	C20—C21—H21A	120.2
C6—C7—H7A	119.5	C22—C21—H21A	120.2
C8—C7—H7A	119.5	C23—C22—C21	121.1 (3)
C7—C8—C3	118.6 (2)	C23—C22—H22A	119.5
C7—C8—C9	119.0 (2)	C21—C22—H22A	119.5
C3—C8—C9	122.3 (2)	C22—C23—C18	120.8 (3)
C8—C9—C18	112.33 (19)	C22—C23—H23A	119.6
C8—C9—C10	114.9 (2)	C18—C23—H23A	119.6
C18—C9—C10	107.8 (2)	O3—C24—O4	124.8 (2)
C8—C9—H9A	107.2	O3—C24—C1	124.5 (2)
C18—C9—H9A	107.2	O4—C24—C1	110.6 (2)
C10—C9—H9A	107.2	O4—C25—C26	107.2 (2)
C9—C10—C1	114.8 (2)	O4—C25—H25A	110.3
C9—C10—H10A	108.6	C26—C25—H25A	110.3
C1—C10—H10A	108.6	O4—C25—H25C	110.3
C9—C10—H10B	108.6	C26—C25—H25C	110.3
C1—C10—H10B	108.6	H25A—C25—H25C	108.5
H10A—C10—H10B	107.6	C25—C26—H26D	109.5
O2—C11—O1	117.8 (3)	C25—C26—H26A	109.5
O2—C11—C1	124.2 (2)	H26D—C26—H26A	109.5
O1—C11—C1	118.1 (2)	C25—C26—H26B	109.5
C13—C12—C17	122.8 (3)	H26D—C26—H26B	109.5
C13—C12—O1	115.9 (3)	H26A—C26—H26B	109.5
C11—C1—C2—C3	−176.57 (18)	C11—O1—C12—C13	158.9 (3)
C24—C1—C2—C3	66.4 (3)	C11—O1—C12—C17	−21.2 (4)
C10—C1—C2—C3	−58.2 (3)	C17—C12—C13—C14	0.4 (5)
C11—C1—C2—C17	−51.9 (3)	O1—C12—C13—C14	−179.7 (3)
C24—C1—C2—C17	−168.91 (19)	C12—C13—C14—C15	0.2 (5)
C10—C1—C2—C17	66.5 (3)	C13—C14—C15—C16	−1.1 (5)
C17—C2—C3—C4	91.6 (3)	C14—C15—C16—C17	1.4 (5)
C1—C2—C3—C4	−147.1 (2)	C13—C12—C17—C16	−0.1 (4)
C17—C2—C3—C8	−87.1 (3)	O1—C12—C17—C16	−180.0 (2)
C1—C2—C3—C8	34.2 (3)	C13—C12—C17—C2	179.9 (3)
C8—C3—C4—C5	0.8 (4)	O1—C12—C17—C2	0.0 (4)
C2—C3—C4—C5	−178.0 (3)	C15—C16—C17—C12	−0.8 (4)
C3—C4—C5—C6	0.0 (4)	C15—C16—C17—C2	179.2 (3)
C4—C5—C6—C7	−1.4 (5)	C3—C2—C17—C12	158.1 (2)
C5—C6—C7—C8	2.1 (4)	C1—C2—C17—C12	35.9 (3)
C6—C7—C8—C3	−1.4 (4)	C3—C2—C17—C16	−21.8 (3)
C6—C7—C8—C9	−179.9 (2)	C1—C2—C17—C16	−144.1 (3)
C4—C3—C8—C7	−0.1 (3)	C8—C9—C18—C19	−32.0 (4)
C2—C3—C8—C7	178.7 (2)	C10—C9—C18—C19	95.5 (3)
C4—C3—C8—C9	178.4 (2)	C8—C9—C18—C23	153.0 (3)
C2—C3—C8—C9	−2.9 (3)	C10—C9—C18—C23	−79.5 (3)
C7—C8—C9—C18	−61.3 (3)	C23—C18—C19—C20	−0.3 (5)
C3—C8—C9—C18	120.3 (2)	C9—C18—C19—C20	−175.4 (3)
C7—C8—C9—C10	175.1 (2)	C18—C19—C20—C21	0.3 (5)
C3—C8—C9—C10	−3.4 (3)	C19—C20—C21—C22	−0.3 (6)
C8—C9—C10—C1	−23.2 (3)	C20—C21—C22—C23	0.2 (5)
C18—C9—C10—C1	−149.2 (2)	C21—C22—C23—C18	−0.3 (5)
C11—C1—C10—C9	174.71 (19)	C19—C18—C23—C22	0.3 (4)
C24—C1—C10—C9	−70.1 (3)	C9—C18—C23—C22	175.5 (3)
C2—C1—C10—C9	54.2 (3)	C25—O4—C24—O3	−10.3 (4)
C12—O1—C11—O2	−177.2 (2)	C25—O4—C24—C1	168.1 (2)
C12—O1—C11—C1	1.3 (4)	C11—C1—C24—O3	108.2 (3)
C24—C1—C11—O2	−24.8 (3)	C10—C1—C24—O3	−8.3 (3)
C10—C1—C11—O2	94.8 (3)	C2—C1—C24—O3	−131.4 (3)
C2—C1—C11—O2	−145.7 (3)	C11—C1—C24—O4	−70.2 (2)
C24—C1—C11—O1	156.8 (2)	C10—C1—C24—O4	173.3 (2)
C10—C1—C11—O1	−83.6 (3)	C2—C1—C24—O4	50.2 (3)
C2—C1—C11—O1	35.9 (3)	C24—O4—C25—C26	175.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4	0.98	2.44	2.815 (3)	102
C6—H6A···O2^i	0.93	2.58	3.449 (4)	156

Symmetry code: (i) x, y+1, z.