[6a,16b]-cis-7,7-Di­methyl-6,6a,7,16b-tetra­hydro­chromeno­[4′,3′:3,4]­pyrano­[3,2-c]-α-naphthocoumarin

Krishna, R.; Selvanayagam, S.; Yogavel, M.; Velmurugan, D.; Manikandan, S.

doi:10.1107/S160053680300789X

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[6a,16b]-cis-7,7-Dimethyl-6,6a,7,16b-tetrahydrochromeno[4′,3′:3,4]pyrano[3,2-c]-α-naphthocoumarin

R. Krishna, S. Selvanayagam, M. Yogavel, D. Velmurugan and S. Manikandan

In the title compound, C₂₅H₂₀O₄, the dihydropyran rings adopt distorted sofa conformations. The molecule comprises two planar regions which form a dihedral angle of 62.56 (3)°. C—H

π interactions link the molecules to form centrosymmetric dimeric pairs. The dimers are interlinked along the [101] direction by C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300789X/ci6219sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680300789X/ci6219Isup2.hkl Contains datablock I

CCDC reference: 214620

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.049
wR factor = 0.153
Data-to-parameter ratio = 14.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

Coumarin derivatives occurring in plants have different biological activities (Cisowski, 1983, 1984). These derivatives are used in oral anticoagulation therapy (Cole et al., 1988; Greenfield, 1988). Coumarin derivatives have been found to be useful in solid state photochemical reactions (Gnanaguru et al., 1985) and in dye lasers (Masilamani, 1979). Coumarin substrates are also used in enzyme determination (Michel & Durant, 1976). The title compound, (I), a coumarin derivative was chosen for crystallographic study to determine its structure and conformation.

The title molecule (Fig. 1) consists of three benzene rings (A, B and F), one pyran ring (C) and two dihydropyran rings (D and E). The molecule contains two planar regions, one comprising of atoms in A, B, C and D rings and other containing atoms in E and F rings. The weighted least-squares planes through these two halves (excluding C17), form a dihedral angle of 62.56 (3)°. The H17—C17—C26—H26 torsion angle at the D and E ring junction is −46.6 (2)°. Both the dihydropyran rings, D and E, adopt distorted sofa conformations with a ΔC_s(C17) asymmetry parameter of 0.070 (1) and 0.026 (1), respectively (Nardelli, 1983); the deviation of C17 from the C3—C4—O15—C16—C26 and C18—O19—C20—C25—C26 planes is 0.623 (2) and 0.633 (2) Å, respectively. All the C—C bond lengths in the title compound agree well with the mean values (Allen et al., 1987). The C2—O1 [1.381 (2) Å], C14—O1 [1.371 (2) Å] and C2—O29 [1.216 (2) Å] distances in the pyran ring agree well with those reported in the related structures (Chinnakali et al., 1998, 1999).

In the crystal, the inversion related molecules are linked to form dimeric pairs by mutual C—H···π interactions (Table 2), C28—H28A···CgA, where CgA is the centroid of the benzene ring A (C9—C13) of the symmetry-related molecule at (1 − x, 1 − y, −z). The dimeric pairs are interlinked by C7—H7···O29ⁱⁱ [symmetry code:(ii) x − 1/2, 3/2 − y, z − 1/2] hydrogen bonds along the [101] direction.

Experimental top

To a refluxing solution of 4-hydroxy-α-naphthocoumarin (1 mmol) in 10 ml of dry ethanol, 2-(3-methyl-2-butenyloxy)benzaldehyde (1 mmol) was added and the reaction mixture was refluxed for 7 h; evaporation of the solvent and flash column chromatography (hexane/ethyl acetate) afforded the title compound as a colourless solid with 22% yield. Single crystals were grown by slow evaporation from a solution in methanol–chloroform (1:1).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of title compound showing 50% probability displacement ellipsoids.
	Fig. 2. Packing of the molecules in the title compound, viewed down the a axis. For clarity, H atoms not involved in hydrogen bonding have been omitted.

[6a,16b]-cis-7,7-Dimethyl-6,6a,7,16b- tetrahydrochromeno[4',3':3,4]pyrano[3,2-c]-α-naphthocoumarin top

Crystal data top

C₂₅H₂₀O₄	F(000) = 808
M_r = 384.41	D_x = 1.324 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 12.172 (1) Å	θ = 15–35°
b = 9.140 (1) Å	µ = 0.72 mm⁻¹
c = 18.081 (1) Å	T = 293 K
β = 106.58 (1)°	Block, colourless
V = 1927.9 (3) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.014
Radiation source: fine-focus sealed tube	θ_max = 71.9°, θ_min = 3.9°
Graphite monochromator	h = 0→15
ω–2θ scans	k = 0→11
3967 measured reflections	l = −22→21
3783 independent reflections	3 standard reflections every 100 reflections
2686 reflections with I > 2σ(I)	intensity decay: none

Refinement top

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0905P)² + 0.3018P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3783 reflections	Δρ_max = 0.20 e Å⁻³
263 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (5)

Crystal data top

C₂₅H₂₀O₄	V = 1927.9 (3) Å³
M_r = 384.41	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 12.172 (1) Å	µ = 0.72 mm⁻¹
b = 9.140 (1) Å	T = 293 K
c = 18.081 (1) Å	0.30 × 0.25 × 0.20 mm
β = 106.58 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.014
3967 measured reflections	3 standard reflections every 100 reflections
3783 independent reflections	intensity decay: none
2686 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
3783 reflections	Δρ_min = −0.25 e Å⁻³
263 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.68391 (10)	0.79519 (16)	0.10818 (7)	0.0528 (4)
C2	0.68450 (16)	0.7257 (2)	0.17611 (10)	0.0508 (5)
C3	0.58192 (15)	0.6570 (2)	0.18167 (9)	0.0440 (4)
C4	0.48988 (14)	0.6497 (2)	0.11790 (9)	0.0417 (4)
C5	0.49193 (14)	0.7184 (2)	0.04648 (9)	0.0430 (4)
C6	0.39750 (16)	0.7161 (2)	−0.02126 (10)	0.0516 (5)
H6	0.3305	0.6674	−0.0211	0.062*
C7	0.40477 (16)	0.7847 (2)	−0.08620 (10)	0.0531 (5)
H7	0.3425	0.7820	−0.1302	0.064*
C8	0.50480 (15)	0.8601 (2)	−0.08835 (9)	0.0452 (4)
C9	0.51411 (18)	0.9306 (2)	−0.15618 (11)	0.0527 (5)
H9	0.4522	0.9295	−0.2004	0.063*
C10	0.6122 (2)	0.9996 (2)	−0.15725 (12)	0.0583 (5)
H10	0.6172	1.0435	−0.2026	0.070*
C11	0.70632 (19)	1.0058 (2)	−0.09097 (12)	0.0597 (5)
H11	0.7725	1.0552	−0.0923	0.072*
C12	0.70080 (17)	0.9394 (2)	−0.02445 (11)	0.0530 (5)
H12	0.7635	0.9433	0.0193	0.064*
C13	0.60074 (15)	0.8649 (2)	−0.02168 (9)	0.0436 (4)
C14	0.58970 (15)	0.7905 (2)	0.04481 (9)	0.0430 (4)
O15	0.39235 (10)	0.57902 (16)	0.11412 (7)	0.0517 (4)
C16	0.37477 (15)	0.5139 (2)	0.18455 (11)	0.0456 (4)
C17	0.49121 (16)	0.4570 (2)	0.23484 (11)	0.0470 (4)
H17	0.5171	0.3844	0.2036	0.056*
C18	0.4903 (2)	0.3799 (2)	0.30928 (13)	0.0616 (6)
H18A	0.4292	0.3079	0.2975	0.074*
H18B	0.5622	0.3277	0.3289	0.074*
O19	0.47520 (15)	0.4735 (2)	0.36842 (9)	0.0742 (5)
C20	0.52330 (19)	0.6102 (3)	0.37570 (11)	0.0598 (6)
C21	0.5152 (2)	0.6896 (4)	0.43913 (13)	0.0804 (8)
H21	0.4833	0.6471	0.4750	0.096*
C22	0.5541 (2)	0.8309 (4)	0.44906 (15)	0.0878 (9)
H22	0.5500	0.8834	0.4922	0.105*
C23	0.5995 (2)	0.8958 (3)	0.39522 (16)	0.0802 (8)
H23	0.6236	0.9927	0.4010	0.096*
C24	0.60862 (19)	0.8146 (3)	0.33238 (12)	0.0613 (6)
H24	0.6399	0.8581	0.2965	0.074*
C25	0.57236 (16)	0.6705 (2)	0.32170 (10)	0.0509 (5)
C26	0.58379 (15)	0.5763 (2)	0.25478 (10)	0.0448 (4)
H26	0.6580	0.5264	0.2722	0.054*
C27	0.31806 (17)	0.6303 (2)	0.21983 (12)	0.0566 (5)
H27A	0.3717	0.7076	0.2397	0.085*
H27B	0.2932	0.5886	0.2611	0.085*
H27C	0.2531	0.6688	0.1812	0.085*
C28	0.2908 (2)	0.3907 (3)	0.15310 (14)	0.0659 (6)
H28A	0.3277	0.3169	0.1308	0.099*
H28B	0.2257	0.4285	0.1144	0.099*
H28C	0.2660	0.3486	0.1943	0.099*
O29	0.77551 (12)	0.7283 (2)	0.22640 (8)	0.0734 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0416 (6)	0.0783 (10)	0.0355 (6)	−0.0165 (6)	0.0060 (5)	0.0084 (6)
C2	0.0420 (9)	0.0735 (14)	0.0350 (8)	−0.0080 (9)	0.0079 (7)	0.0073 (9)
C3	0.0413 (9)	0.0565 (11)	0.0352 (8)	−0.0029 (8)	0.0126 (7)	0.0027 (8)
C4	0.0350 (8)	0.0533 (10)	0.0391 (8)	−0.0036 (7)	0.0142 (7)	−0.0002 (8)
C5	0.0375 (9)	0.0579 (11)	0.0339 (8)	−0.0039 (8)	0.0108 (7)	−0.0005 (8)
C6	0.0392 (9)	0.0742 (14)	0.0397 (9)	−0.0080 (9)	0.0087 (7)	−0.0024 (9)
C7	0.0441 (10)	0.0752 (14)	0.0366 (9)	0.0014 (9)	0.0061 (7)	−0.0008 (9)
C8	0.0518 (10)	0.0504 (10)	0.0346 (8)	0.0050 (8)	0.0141 (7)	−0.0008 (8)
C9	0.0675 (12)	0.0525 (11)	0.0385 (9)	0.0088 (10)	0.0157 (8)	0.0040 (8)
C10	0.0824 (14)	0.0521 (12)	0.0466 (10)	0.0051 (11)	0.0283 (10)	0.0088 (9)
C11	0.0701 (13)	0.0575 (13)	0.0600 (12)	−0.0119 (11)	0.0323 (10)	0.0019 (10)
C12	0.0548 (11)	0.0606 (12)	0.0455 (10)	−0.0092 (9)	0.0173 (8)	0.0013 (9)
C13	0.0474 (9)	0.0505 (10)	0.0355 (8)	−0.0027 (8)	0.0159 (7)	−0.0020 (8)
C14	0.0379 (8)	0.0581 (11)	0.0322 (8)	−0.0032 (8)	0.0087 (6)	−0.0013 (7)
O15	0.0405 (6)	0.0710 (9)	0.0454 (7)	−0.0114 (6)	0.0150 (5)	0.0052 (6)
C16	0.0440 (9)	0.0460 (10)	0.0536 (10)	−0.0024 (8)	0.0248 (8)	0.0046 (8)
C17	0.0494 (10)	0.0454 (10)	0.0535 (10)	0.0080 (8)	0.0264 (8)	0.0046 (8)
C18	0.0693 (13)	0.0545 (12)	0.0707 (14)	0.0104 (10)	0.0353 (11)	0.0172 (10)
O19	0.0956 (12)	0.0789 (11)	0.0657 (9)	0.0106 (10)	0.0513 (9)	0.0170 (8)
C20	0.0644 (13)	0.0738 (15)	0.0452 (10)	0.0197 (11)	0.0220 (9)	0.0104 (10)
C21	0.0923 (18)	0.105 (2)	0.0498 (12)	0.0325 (17)	0.0304 (12)	0.0051 (13)
C22	0.0889 (18)	0.112 (2)	0.0608 (15)	0.0295 (18)	0.0194 (13)	−0.0225 (16)
C23	0.0783 (16)	0.0783 (17)	0.0729 (16)	0.0158 (14)	0.0035 (13)	−0.0183 (13)
C24	0.0589 (12)	0.0695 (14)	0.0495 (11)	0.0082 (11)	0.0058 (9)	−0.0006 (10)
C25	0.0476 (10)	0.0636 (12)	0.0403 (9)	0.0114 (9)	0.0109 (7)	0.0060 (9)
C26	0.0439 (9)	0.0540 (11)	0.0391 (9)	0.0038 (8)	0.0162 (7)	0.0069 (8)
C27	0.0539 (11)	0.0575 (12)	0.0645 (12)	0.0108 (9)	0.0268 (10)	0.0052 (10)
C28	0.0615 (13)	0.0586 (13)	0.0824 (15)	−0.0109 (10)	0.0279 (11)	−0.0015 (11)
O29	0.0465 (8)	0.1216 (14)	0.0433 (7)	−0.0230 (8)	−0.0011 (6)	0.0180 (8)

Geometric parameters (Å, º) top

O1—C14	1.371 (2)	C16—C28	1.518 (3)
O1—C2	1.381 (2)	C16—C17	1.540 (3)
C2—O29	1.216 (2)	C17—C18	1.522 (3)
C2—C3	1.427 (2)	C17—C26	1.535 (3)
C3—C4	1.361 (2)	C17—H17	0.98
C3—C26	1.508 (2)	C18—O19	1.422 (3)
C4—O15	1.336 (2)	C18—H18A	0.97
C4—C5	1.443 (2)	C18—H18B	0.97
C5—C14	1.368 (2)	O19—C20	1.370 (3)
C5—C6	1.421 (2)	C20—C21	1.385 (3)
C6—C7	1.356 (3)	C20—C25	1.395 (3)
C6—H6	0.93	C21—C22	1.370 (4)
C7—C8	1.409 (3)	C21—H21	0.93
C7—H7	0.93	C22—C23	1.382 (4)
C8—C9	1.418 (2)	C22—H22	0.93
C8—C13	1.420 (2)	C23—C24	1.388 (3)
C9—C10	1.356 (3)	C23—H23	0.93
C9—H9	0.93	C24—C25	1.385 (3)
C10—C11	1.403 (3)	C24—H24	0.93
C10—H10	0.93	C25—C26	1.523 (3)
C11—C12	1.366 (3)	C26—H26	0.98
C11—H11	0.93	C27—H27A	0.96
C12—C13	1.409 (3)	C27—H27B	0.96
C12—H12	0.93	C27—H27C	0.96
C13—C14	1.420 (2)	C28—H28A	0.96
O15—C16	1.476 (2)	C28—H28B	0.96
C16—C27	1.505 (3)	C28—H28C	0.96

C14—O1—C2	121.31 (14)	C18—C17—C16	116.18 (15)
O29—C2—O1	115.36 (16)	C26—C17—C16	112.90 (15)
O29—C2—C3	125.78 (17)	C18—C17—H17	106.3
O1—C2—C3	118.86 (15)	C26—C17—H17	106.3
C4—C3—C2	119.17 (16)	C16—C17—H17	106.3
C4—C3—C26	121.43 (16)	O19—C18—C17	114.94 (17)
C2—C3—C26	118.84 (15)	O19—C18—H18A	108.5
O15—C4—C3	124.88 (16)	C17—C18—H18A	108.5
O15—C4—C5	114.00 (14)	O19—C18—H18B	108.5
C3—C4—C5	121.11 (16)	C17—C18—H18B	108.5
C14—C5—C6	118.87 (16)	H18A—C18—H18B	107.5
C14—C5—C4	117.83 (15)	C20—O19—C18	118.51 (15)
C6—C5—C4	123.30 (16)	O19—C20—C21	115.4 (2)
C7—C6—C5	120.21 (17)	O19—C20—C25	123.34 (19)
C7—C6—H6	119.9	C21—C20—C25	121.2 (2)
C5—C6—H6	119.9	C22—C21—C20	119.9 (3)
C6—C7—C8	121.36 (16)	C22—C21—H21	120.0
C6—C7—H7	119.3	C20—C21—H21	120.0
C8—C7—H7	119.3	C21—C22—C23	120.3 (2)
C7—C8—C9	121.94 (17)	C21—C22—H22	119.8
C7—C8—C13	119.96 (16)	C23—C22—H22	119.8
C9—C8—C13	118.10 (17)	C22—C23—C24	119.2 (3)
C10—C9—C8	120.79 (18)	C22—C23—H23	120.4
C10—C9—H9	119.6	C24—C23—H23	120.4
C8—C9—H9	119.6	C25—C24—C23	121.7 (2)
C9—C10—C11	120.95 (18)	C25—C24—H24	119.1
C9—C10—H10	119.5	C23—C24—H24	119.1
C11—C10—H10	119.5	C24—C25—C20	117.5 (2)
C12—C11—C10	120.07 (19)	C24—C25—C26	123.40 (18)
C12—C11—H11	120.0	C20—C25—C26	119.14 (19)
C10—C11—H11	120.0	C3—C26—C25	115.97 (16)
C11—C12—C13	120.43 (19)	C3—C26—C17	108.37 (14)
C11—C12—H12	119.8	C25—C26—C17	111.14 (14)
C13—C12—H12	119.8	C3—C26—H26	107.0
C12—C13—C8	119.64 (16)	C25—C26—H26	107.0
C12—C13—C14	123.58 (16)	C17—C26—H26	107.0
C8—C13—C14	116.77 (16)	C16—C27—H27A	109.5
C5—C14—O1	121.47 (16)	C16—C27—H27B	109.5
C5—C14—C13	122.83 (16)	H27A—C27—H27B	109.5
O1—C14—C13	115.70 (15)	C16—C27—H27C	109.5
C4—O15—C16	119.77 (13)	H27A—C27—H27C	109.5
O15—C16—C27	106.10 (15)	H27B—C27—H27C	109.5
O15—C16—C28	102.94 (15)	C16—C28—H28A	109.5
C27—C16—C28	110.00 (16)	C16—C28—H28B	109.5
O15—C16—C17	108.08 (13)	H28A—C28—H28B	109.5
C27—C16—C17	116.39 (16)	C16—C28—H28C	109.5
C28—C16—C17	112.25 (17)	H28A—C28—H28C	109.5
C18—C17—C26	108.12 (16)	H28B—C28—H28C	109.5

C14—O1—C2—O29	174.79 (19)	C3—C4—O15—C16	6.0 (3)
C14—O1—C2—C3	−4.6 (3)	C5—C4—O15—C16	−175.06 (15)
O29—C2—C3—C4	−173.1 (2)	C4—O15—C16—C27	90.5 (2)
O1—C2—C3—C4	6.2 (3)	C4—O15—C16—C28	−153.9 (2)
O29—C2—C3—C26	−1.6 (3)	C4—O15—C16—C17	−35.0 (2)
O1—C2—C3—C26	177.76 (17)	O15—C16—C17—C18	−177.69 (16)
C2—C3—C4—O15	174.76 (18)	C27—C16—C17—C18	63.1 (2)
C26—C3—C4—O15	3.4 (3)	C28—C16—C17—C18	−64.9 (2)
C2—C3—C4—C5	−4.1 (3)	O15—C16—C17—C26	56.59 (19)
C26—C3—C4—C5	−175.5 (2)	C27—C16—C17—C26	−62.6 (2)
O15—C4—C5—C14	−178.61 (17)	C28—C16—C17—C26	169.42 (15)
C3—C4—C5—C14	0.4 (3)	C26—C17—C18—O19	55.3 (2)
O15—C4—C5—C6	2.2 (3)	C16—C17—C18—O19	−72.8 (2)
C3—C4—C5—C6	−178.86 (19)	C17—C18—O19—C20	−35.4 (3)
C14—C5—C6—C7	−0.1 (3)	C18—O19—C20—C21	−173.70 (19)
C4—C5—C6—C7	179.11 (19)	C18—O19—C20—C25	9.4 (3)
C5—C6—C7—C8	−0.3 (3)	O19—C20—C21—C22	−175.9 (2)
C6—C7—C8—C9	179.13 (19)	C25—C20—C21—C22	1.0 (4)
C6—C7—C8—C13	0.2 (3)	C20—C21—C22—C23	1.3 (4)
C7—C8—C9—C10	−178.52 (19)	C21—C22—C23—C24	−2.1 (4)
C13—C8—C9—C10	0.5 (3)	C22—C23—C24—C25	0.7 (3)
C8—C9—C10—C11	−1.3 (3)	C23—C24—C25—C20	1.5 (3)
C9—C10—C11—C12	1.2 (3)	C23—C24—C25—C26	−178.29 (19)
C10—C11—C12—C13	−0.3 (3)	O19—C20—C25—C24	174.3 (2)
C11—C12—C13—C8	−0.6 (3)	C21—C20—C25—C24	−2.4 (3)
C11—C12—C13—C14	178.51 (19)	O19—C20—C25—C26	−5.9 (3)
C7—C8—C13—C12	179.47 (18)	C21—C20—C25—C26	177.44 (19)
C9—C8—C13—C12	0.5 (3)	C4—C3—C26—C25	−107.7 (2)
C7—C8—C13—C14	0.3 (3)	C2—C3—C26—C25	81.0 (2)
C9—C8—C13—C14	−178.64 (17)	C4—C3—C26—C17	18.1 (2)
C6—C5—C14—O1	−179.4 (2)	C2—C3—C26—C17	−153.29 (17)
C4—C5—C14—O1	1.4 (3)	C24—C25—C26—C3	−28.5 (2)
C6—C5—C14—C13	0.7 (3)	C20—C25—C26—C3	151.63 (17)
C4—C5—C14—C13	−178.59 (17)	C24—C25—C26—C17	−152.88 (17)
C2—O1—C14—C5	0.8 (3)	C20—C25—C26—C17	27.3 (2)
C2—O1—C14—C13	−179.22 (17)	C18—C17—C26—C3	−177.81 (15)
C12—C13—C14—C5	−179.86 (19)	C16—C17—C26—C3	−47.87 (19)
C8—C13—C14—C5	−0.8 (3)	C18—C17—C26—C25	−49.28 (19)
C12—C13—C14—O1	0.2 (3)	C16—C17—C26—C25	80.67 (18)
C8—C13—C14—O1	179.27 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28A···CgAⁱ	0.96	2.60	3.530 (3)	163
C7—H7···O29ⁱⁱ	0.93	2.49	3.306 (2)	147

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₀O₄
M_r	384.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.172 (1), 9.140 (1), 18.081 (1)
β (°)	106.58 (1)
V (Å³)	1927.9 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3967, 3783, 2686
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.153, 1.02
No. of reflections	3783
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia,1997) and PLATON (Spek, 1990), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top

O1—C14	1.371 (2)	C16—C27	1.505 (3)
O1—C2	1.381 (2)	C16—C28	1.518 (3)
C2—O29	1.216 (2)	C16—C17	1.540 (3)
C2—C3	1.427 (2)	C17—C18	1.522 (3)
C3—C4	1.361 (2)	C17—C26	1.535 (3)
C3—C26	1.508 (2)	C18—O19	1.422 (3)
C4—O15	1.336 (2)	O19—C20	1.370 (3)
C4—C5	1.443 (2)	C21—C22	1.370 (4)
C5—C14	1.368 (2)	C25—C26	1.523 (3)
O15—C16	1.476 (2)

C14—O1—C2	121.31 (14)	C5—C14—O1	121.47 (16)
O29—C2—O1	115.36 (16)	C4—O15—C16	119.77 (13)
O29—C2—C3	125.78 (17)	O15—C16—C27	106.10 (15)
O1—C2—C3	118.86 (15)	O15—C16—C28	102.94 (15)
O15—C4—C3	124.88 (16)	O19—C20—C21	115.4 (2)
O15—C4—C5	114.00 (14)	O19—C20—C25	123.34 (19)

C26—C3—C4—C5	−175.5 (2)	C4—O15—C16—C28	−153.9 (2)
C6—C5—C14—O1	−179.4 (2)	O19—C20—C25—C24	174.3 (2)
C4—O15—C16—C27	90.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28A···CgAⁱ	0.96	2.60	3.530 (3)	163
C7—H7···O29ⁱⁱ	0.93	2.49	3.306 (2)	147

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+3/2, z−1/2.

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