5-Meth­oxy-2,2-dimethyl-6-[(2E)-2-methyl­but-2-eno­yl]-10-phenyl-2H,8H-pyrano[2,3-f]chromen-8-one (calophyllolide)

Kalyanaraman, L.; Mohan Kumar, R.; Vishweshwar, P.; Pichai, R.; Narasimhan, S.

doi:10.1107/S1600536810013577

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1115

https://doi.org/10.1107/S1600536810013577

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5-Methoxy-2,2-dimethyl-6-[(2E)-2-methylbut-2-enoyl]-10-phenyl-2H,8H-pyrano[2,3-f]chromen-8-one (calophyllolide)

L. Kalyanaraman,^a R. Mohan Kumar,^b Peddy Vishweshwar,^c ^*‡ R. Pichai ^a and S. Narasimhan ^b

^aDepartment of Chemistry, Presidency College, Chennai 600 005, India, ^bAsthagiri Herbal Research Foundation, 14/1, II Main road, Jayanagar, Tambaram Sanatorium, Chennai 600 047, India, and ^cDepartment of Analytical Research, Discovery Research, Dr Reddy's Laboratories Ltd, Miyapur, Hyderabad 500 049, India
^*Correspondence e-mail: peddy_vishu@yahoo.co.in

(Received 29 March 2010; accepted 13 April 2010; online 17 April 2010)

The title compound, C₂₆H₂₄O₅, was isolated from calophyllum inophyllum seeds. In the molecule, the phenyl and 2-methylbut-2-enoyl groups are almost orthogonal to the chromene fragment [C—C—C—C torsion angles = 81.4 (3) and −90.1 (2)°, respectively]. In the crystal packing, centrosymmetrically related molecules are linked by C—H⋯O contacts into dimers, which are connected via further C—H⋯O interactions into a double chain along [010].

Related literature

For information on weak hydrogen bonds, see: Desiraju & Steiner (1999 ). For the Chebychev polynomial used in the weighting scheme, see: Carruthers & Watkin, (1979 ).

Experimental

Crystal data

C₂₆H₂₄O₅
M_r = 416.47
Triclinic, $[P \overline 1]$
a = 8.943 (3) Å
b = 11.559 (4) Å
c = 12.171 (3) Å
α = 96.238 (8)°
β = 104.041 (5)°
γ = 110.301 (8)°
V = 1118.7 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.50 × 0.50 mm

Data collection

Rigaku Mercury diffractometer
12333 measured reflections
4480 independent reflections
2706 reflections with F² > 2σ(F²)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.092
S = 0.96
4480 reflections
304 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2ⁱ	0.95	2.44	3.381 (3)	172
C26—H26⋯O5ⁱⁱ	0.95	2.40	3.225 (3)	145
Symmetry codes: (i) x, y-1, z; (ii) -x+2, -y+2, -z+1.

Data collection: CrystalClear (Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2006 ); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810013577/tk2651sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013577/tk2651Isup2.hkl

checkCIF report

Comment top

The molecular structure of (I), Fig. 1, shows that the phenyl and 2-methylbut-2-enoyl groups are almost orthogonal to the chromene fragment as seen in the C9–C3–C21–C22 and C6–C7–C16–C17 torsion angles of 81.4 (3)° and -90.1 (2)°, respectively. In the crystal, two molecules are linked by a pair of C26–H26···O5 contacts (Desiraju & Steiner, 1999), to form a centrosymmetric dimer, Table 1. The dimers thus formed are connected by C11–H11···O2 contacts to form a double chain along [010]; Fig. 2 and Table 1.

Related literature top

For information on weak hydrogen bonds, see: Desiraju & Steiner (1999). For the Chebychev polynomial used in the weighting scheme, see: Carruthers & Watkin, (1979).

Experimental top

Calophyllolide (I) is the major constituent of Calophyllum inophyllum seed. Seeds, which were collected from the coastal Tamil Nadu (India), were dried in the shade and powdered. Soxhlet extraction was performed to extract (I) from the seed powder using n-hexane. The compound was purified by silica column chromatography using n-hexane and ethyl acetate as eluent. Compound (I) (ca. 20 mg) was dissolved in a solvent mixture comprising n-hexane (8 ml) and acetone (2 ml). Slow evaporation at room temperature yielded crystals after a few days.

Structure description top

For information on weak hydrogen bonds, see: Desiraju & Steiner (1999). For the Chebychev polynomial used in the weighting scheme, see: Carruthers & Watkin, (1979).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2006); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: CrystalStructure (Molecular Structure Corporation & Rigaku, 2006).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. A view of the double chain in (I) sustained by C–H···O contacts shown as dashed lines..

5-Methoxy-2,2-dimethyl-6-[(2E)-2-methylbut-2-enoyl]-10-phenyl- 2H,8H-pyrano[2,3-f]chromen-8-one top

Crystal data top

C₂₆H₂₄O₅	Z = 2
M_r = 416.47	F(000) = 440.00
Triclinic, P1	D_x = 1.236 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 8.943 (3) Å	Cell parameters from 4735 reflections
b = 11.559 (4) Å	θ = 2.5–27.4°
c = 12.171 (3) Å	µ = 0.09 mm⁻¹
α = 96.238 (8)°	T = 298 K
β = 104.041 (5)°	Prism, colorless
γ = 110.301 (8)°	0.50 × 0.50 × 0.50 mm
V = 1118.7 (6) Å³

Data collection top

Rigaku Mercury diffractometer	R_int = 0.055
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.4°
ω scans	h = −11→11
12333 measured reflections	k = −14→11
4480 independent reflections	l = −15→15
2706 reflections with F² > 2σ(F²)

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.078	Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979): 26851.8000, 36815.3000, 10053.3000
wR(F²) = 0.092	(Δ/σ)_max = 0.018
S = 0.96	Δρ_max = 0.34 e Å⁻³
4480 reflections	Δρ_min = −0.31 e Å⁻³
304 parameters

Crystal data top

C₂₆H₂₄O₅	γ = 110.301 (8)°
M_r = 416.47	V = 1118.7 (6) Å³
Triclinic, P1	Z = 2
a = 8.943 (3) Å	Mo Kα radiation
b = 11.559 (4) Å	µ = 0.09 mm⁻¹
c = 12.171 (3) Å	T = 298 K
α = 96.238 (8)°	0.50 × 0.50 × 0.50 mm
β = 104.041 (5)°

Data collection top

Rigaku Mercury diffractometer	2706 reflections with F² > 2σ(F²)
12333 measured reflections	R_int = 0.055
4480 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	304 parameters
wR(F²) = 0.092	H-atom parameters constrained
S = 0.96	Δρ_max = 0.34 e Å⁻³
4480 reflections	Δρ_min = −0.31 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.76337 (17)	1.04526 (10)	0.54924 (11)	0.0565 (4)
O2	0.6788 (2)	1.17903 (13)	0.46095 (14)	0.0901 (7)
O3	0.61388 (16)	0.61390 (10)	0.36909 (10)	0.0549 (4)
O4	0.97605 (19)	0.78784 (14)	0.75890 (11)	0.0674 (5)
O5	1.1027 (2)	1.10050 (18)	0.75198 (16)	0.1159 (8)
C1	0.6716 (2)	1.07075 (17)	0.45404 (18)	0.0615 (7)
C2	0.5705 (2)	0.96723 (17)	0.35769 (17)	0.0598 (7)
C3	0.5714 (2)	0.85017 (16)	0.35387 (15)	0.0478 (5)
C4	0.7000 (2)	0.71305 (14)	0.46131 (14)	0.0454 (5)
C5	0.7989 (2)	0.69796 (16)	0.56201 (15)	0.0508 (5)
C6	0.8849 (2)	0.80206 (17)	0.65664 (15)	0.0519 (6)
C7	0.8693 (2)	0.91656 (15)	0.65085 (15)	0.0484 (5)
C8	0.7687 (2)	0.92695 (14)	0.54971 (15)	0.0449 (5)
C9	0.6773 (2)	0.82733 (14)	0.45266 (13)	0.0417 (5)
C10	0.6832 (2)	0.51684 (16)	0.35424 (17)	0.0589 (6)
C11	0.7414 (3)	0.48607 (17)	0.4694 (2)	0.0740 (8)
C12	0.8001 (3)	0.57273 (18)	0.56640 (19)	0.0688 (8)
C13	0.8261 (3)	0.5703 (2)	0.3035 (2)	0.0845 (10)
C14	0.5371 (3)	0.40608 (18)	0.2700 (2)	0.0821 (9)
C15	1.1373 (3)	0.7892 (2)	0.7603 (2)	0.0913 (10)
C16	0.9666 (2)	1.02968 (17)	0.75119 (16)	0.0569 (6)
C17	0.8941 (2)	1.05157 (16)	0.84342 (15)	0.0540 (6)
C18	0.7537 (2)	0.9633 (2)	0.84800 (17)	0.0637 (7)
C19	0.6672 (3)	0.9685 (3)	0.9381 (2)	0.1058 (11)
C20	0.9897 (3)	1.1736 (2)	0.9313 (2)	0.0908 (9)
C21	0.4565 (2)	0.74887 (17)	0.24960 (15)	0.0530 (5)
C22	0.3021 (2)	0.6686 (2)	0.25190 (19)	0.0747 (8)
C23	0.1968 (3)	0.5724 (2)	0.1561 (2)	0.0879 (9)
C24	0.2434 (3)	0.5585 (2)	0.0590 (2)	0.0906 (9)
C25	0.3941 (3)	0.6396 (2)	0.0550 (2)	0.1014 (10)
C26	0.5003 (3)	0.7362 (2)	0.14927 (19)	0.0842 (9)
H2	0.50080	0.98190	0.29290	0.0750*
H11	0.73470	0.40280	0.47280	0.0930*
H12	0.84350	0.55350	0.63820	0.0880*
H18	0.70430	0.88900	0.78860	0.0790*
H22	0.26760	0.67840	0.31910	0.0850*
H23	0.09120	0.51610	0.15790	0.0930*
H24	0.17210	0.49190	−0.00560	0.0950*
H25	0.42410	0.63110	−0.01430	0.1080*
H26	0.60490	0.79210	0.14550	0.0910*
H131	0.90770	0.53590	0.32850	0.1110*
H132	0.87580	0.65960	0.32870	0.1110*
H133	0.78370	0.54880	0.22140	0.1110*
H141	0.47650	0.35420	0.31270	0.0950*
H142	0.57630	0.35810	0.22430	0.0940*
H143	0.46610	0.43660	0.22100	0.0950*
H151	1.12660	0.70530	0.73490	0.1170*
H152	1.21370	0.82260	0.83630	0.1170*
H153	1.17770	0.83980	0.70910	0.1170*
H191	0.55050	0.92150	0.90490	0.1330*
H192	0.70940	0.93440	1.00040	0.1340*
H193	0.68690	1.05410	0.96610	0.1340*
H201	0.91510	1.20110	0.95980	0.1020*
H202	1.06610	1.16130	0.99370	0.1020*
H203	1.04970	1.23560	0.89570	0.1020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0749 (8)	0.0356 (5)	0.0624 (7)	0.0231 (5)	0.0257 (6)	0.0064 (5)
O2	0.1485 (16)	0.0520 (8)	0.0941 (12)	0.0577 (9)	0.0467 (11)	0.0257 (7)
O3	0.0728 (8)	0.0364 (6)	0.0526 (7)	0.0220 (5)	0.0166 (6)	0.0006 (5)
O4	0.0794 (9)	0.0817 (9)	0.0477 (7)	0.0397 (8)	0.0165 (6)	0.0176 (6)
O5	0.0764 (11)	0.1121 (14)	0.1056 (14)	−0.0198 (10)	0.0414 (10)	−0.0323 (11)
C1	0.0890 (14)	0.0468 (10)	0.0662 (12)	0.0374 (10)	0.0333 (11)	0.0212 (9)
C2	0.0729 (13)	0.0520 (10)	0.0637 (12)	0.0328 (9)	0.0215 (10)	0.0180 (9)
C3	0.0525 (9)	0.0482 (9)	0.0495 (9)	0.0226 (8)	0.0214 (7)	0.0137 (7)
C4	0.0584 (10)	0.0343 (7)	0.0465 (9)	0.0180 (7)	0.0216 (7)	0.0068 (6)
C5	0.0688 (11)	0.0441 (8)	0.0489 (9)	0.0269 (8)	0.0256 (8)	0.0124 (7)
C6	0.0617 (11)	0.0575 (10)	0.0430 (9)	0.0266 (8)	0.0207 (8)	0.0140 (7)
C7	0.0533 (10)	0.0438 (8)	0.0486 (9)	0.0175 (7)	0.0196 (7)	0.0060 (7)
C8	0.0539 (9)	0.0328 (7)	0.0514 (9)	0.0179 (7)	0.0214 (8)	0.0055 (6)
C9	0.0520 (9)	0.0362 (7)	0.0413 (8)	0.0194 (7)	0.0183 (7)	0.0086 (6)
C10	0.0787 (13)	0.0371 (8)	0.0656 (12)	0.0253 (8)	0.0287 (10)	0.0042 (7)
C11	0.1114 (18)	0.0362 (9)	0.0839 (15)	0.0360 (11)	0.0336 (13)	0.0157 (9)
C12	0.1012 (16)	0.0529 (10)	0.0658 (13)	0.0406 (11)	0.0283 (12)	0.0234 (9)
C13	0.1012 (18)	0.0680 (13)	0.1079 (19)	0.0420 (13)	0.0576 (16)	0.0221 (12)
C14	0.0934 (17)	0.0468 (11)	0.0952 (17)	0.0213 (11)	0.0294 (13)	−0.0107 (10)
C15	0.0966 (18)	0.119 (2)	0.0764 (16)	0.0670 (17)	0.0208 (13)	0.0192 (14)
C16	0.0543 (11)	0.0483 (9)	0.0573 (11)	0.0117 (8)	0.0144 (8)	0.0015 (8)
C17	0.0714 (12)	0.0495 (9)	0.0412 (9)	0.0298 (9)	0.0105 (8)	0.0034 (7)
C18	0.0734 (13)	0.0721 (12)	0.0526 (11)	0.0333 (11)	0.0244 (9)	0.0116 (9)
C19	0.114 (2)	0.148 (2)	0.0715 (16)	0.055 (2)	0.0482 (16)	0.0263 (16)
C20	0.122 (2)	0.0685 (14)	0.0641 (14)	0.0308 (14)	0.0172 (13)	−0.0123 (11)
C21	0.0577 (10)	0.0509 (9)	0.0486 (9)	0.0192 (8)	0.0136 (8)	0.0150 (7)
C22	0.0653 (13)	0.0826 (14)	0.0635 (13)	0.0144 (11)	0.0186 (10)	0.0149 (11)
C23	0.0701 (15)	0.0864 (16)	0.0759 (15)	0.0031 (12)	0.0088 (12)	0.0147 (13)
C24	0.0828 (17)	0.0856 (17)	0.0683 (15)	0.0129 (14)	−0.0020 (13)	−0.0004 (13)
C25	0.0934 (19)	0.120 (2)	0.0559 (13)	0.0087 (16)	0.0222 (13)	−0.0095 (14)
C26	0.0747 (15)	0.0923 (17)	0.0604 (13)	0.0053 (13)	0.0248 (11)	−0.0031 (12)

Geometric parameters (Å, º) top

O1—C1	1.372 (2)	C21—C26	1.378 (3)
O1—C8	1.385 (2)	C22—C23	1.393 (3)
O2—C1	1.223 (2)	C23—C24	1.357 (4)
O3—C4	1.362 (2)	C24—C25	1.365 (4)
O3—C10	1.473 (2)	C25—C26	1.386 (3)
O4—C6	1.373 (2)	C2—H2	0.9500
O4—C15	1.433 (3)	C11—H11	0.9500
O5—C16	1.205 (3)	C12—H12	0.9500
C1—C2	1.433 (3)	C13—H131	0.9500
C2—C3	1.352 (3)	C13—H132	0.9500
C3—C9	1.450 (2)	C13—H133	0.9500
C3—C21	1.499 (3)	C14—H141	0.9500
C4—C5	1.394 (2)	C14—H142	0.9500
C4—C9	1.415 (2)	C14—H143	0.9500
C5—C6	1.412 (3)	C15—H151	0.9500
C5—C12	1.458 (3)	C15—H152	0.9500
C6—C7	1.386 (3)	C15—H153	0.9500
C7—C8	1.382 (3)	C18—H18	0.9500
C7—C16	1.519 (3)	C19—H191	0.9500
C8—C9	1.404 (2)	C19—H192	0.9500
C10—C11	1.498 (3)	C19—H193	0.9500
C10—C13	1.521 (3)	C20—H201	0.9500
C10—C14	1.517 (3)	C20—H202	0.9500
C11—C12	1.323 (3)	C20—H203	0.9500
C16—C17	1.466 (3)	C22—H22	0.9500
C17—C18	1.333 (3)	C23—H23	0.9500
C17—C20	1.502 (3)	C24—H24	0.9500
C18—C19	1.495 (3)	C25—H25	0.9500
C21—C22	1.380 (3)	C26—H26	0.9500

C1—O1—C8	121.76 (14)	C21—C26—C25	120.1 (2)
C4—O3—C10	117.74 (14)	C1—C2—H2	118.00
C6—O4—C15	115.00 (16)	C3—C2—H2	118.00
O1—C1—O2	116.84 (18)	C10—C11—H11	119.00
O1—C1—C2	117.20 (16)	C12—C11—H11	120.00
O2—C1—C2	125.90 (19)	C5—C12—H12	120.00
C1—C2—C3	123.13 (18)	C11—C12—H12	120.00
C2—C3—C9	118.60 (16)	C10—C13—H131	110.00
C2—C3—C21	118.10 (17)	C10—C13—H132	110.00
C9—C3—C21	123.24 (15)	C10—C13—H133	109.00
O3—C4—C5	120.05 (15)	H131—C13—H132	109.00
O3—C4—C9	117.64 (15)	H131—C13—H133	110.00
C5—C4—C9	122.22 (15)	H132—C13—H133	109.00
C4—C5—C6	118.71 (16)	C10—C14—H141	109.00
C4—C5—C12	117.92 (16)	C10—C14—H142	110.00
C6—C5—C12	123.27 (17)	C10—C14—H143	109.00
O4—C6—C5	119.82 (17)	H141—C14—H142	109.00
O4—C6—C7	119.10 (16)	H141—C14—H143	109.00
C5—C6—C7	120.92 (16)	H142—C14—H143	110.00
C6—C7—C8	118.42 (16)	O4—C15—H151	109.00
C6—C7—C16	120.80 (16)	O4—C15—H152	111.00
C8—C7—C16	120.72 (15)	O4—C15—H153	109.00
O1—C8—C7	115.05 (15)	H151—C15—H152	109.00
O1—C8—C9	120.94 (15)	H151—C15—H153	110.00
C7—C8—C9	124.01 (15)	H152—C15—H153	109.00
C3—C9—C4	126.22 (15)	C17—C18—H18	117.00
C3—C9—C8	118.14 (15)	C19—C18—H18	117.00
C4—C9—C8	115.64 (15)	C18—C19—H191	110.00
O3—C10—C11	109.14 (16)	C18—C19—H192	110.00
O3—C10—C13	107.16 (15)	C18—C19—H193	109.00
O3—C10—C14	103.60 (16)	H191—C19—H192	110.00
C11—C10—C13	111.86 (19)	H191—C19—H193	109.00
C11—C10—C14	112.31 (16)	H192—C19—H193	109.00
C13—C10—C14	112.28 (18)	C17—C20—H201	110.00
C10—C11—C12	121.01 (18)	C17—C20—H202	109.00
C5—C12—C11	119.6 (2)	C17—C20—H203	109.00
O5—C16—C7	118.35 (18)	H201—C20—H202	110.00
O5—C16—C17	121.52 (18)	H201—C20—H203	109.00
C7—C16—C17	120.12 (16)	H202—C20—H203	109.00
C16—C17—C18	119.84 (17)	C21—C22—H22	120.00
C16—C17—C20	116.41 (18)	C23—C22—H22	120.00
C18—C17—C20	123.71 (19)	C22—C23—H23	120.00
C17—C18—C19	126.6 (2)	C24—C23—H23	119.00
C3—C21—C22	120.04 (17)	C23—C24—H24	120.00
C3—C21—C26	121.08 (18)	C25—C24—H24	120.00
C22—C21—C26	118.86 (19)	C24—C25—H25	119.00
C21—C22—C23	120.1 (2)	C26—C25—H25	120.00
C22—C23—C24	120.4 (2)	C21—C26—H26	120.00
C23—C24—C25	119.8 (2)	C25—C26—H26	120.00
C24—C25—C26	120.7 (2)

C8—O1—C1—O2	−177.92 (18)	C6—C5—C12—C11	−168.4 (2)
C8—O1—C1—C2	4.8 (3)	O4—C6—C7—C8	−176.02 (18)
C1—O1—C8—C7	178.65 (17)	O4—C6—C7—C16	6.7 (3)
C1—O1—C8—C9	−1.1 (3)	C5—C6—C7—C8	−0.6 (3)
C10—O3—C4—C5	−28.4 (2)	C5—C6—C7—C16	−177.87 (17)
C10—O3—C4—C9	155.07 (16)	C6—C7—C8—O1	−178.13 (17)
C4—O3—C10—C11	43.8 (2)	C6—C7—C8—C9	1.6 (3)
C4—O3—C10—C13	−77.49 (19)	C16—C7—C8—O1	−0.9 (3)
C4—O3—C10—C14	163.64 (15)	C16—C7—C8—C9	178.89 (18)
C15—O4—C6—C5	79.4 (2)	C6—C7—C16—O5	90.6 (2)
C15—O4—C6—C7	−105.2 (2)	C6—C7—C16—C17	−90.1 (2)
O1—C1—C2—C3	−4.8 (3)	C8—C7—C16—O5	−86.6 (3)
O2—C1—C2—C3	178.1 (2)	C8—C7—C16—C17	92.8 (2)
C1—C2—C3—C9	1.1 (3)	O1—C8—C9—C3	−2.7 (3)
C1—C2—C3—C21	178.37 (18)	O1—C8—C9—C4	176.71 (16)
C2—C3—C9—C4	−176.70 (19)	C7—C8—C9—C3	177.57 (18)
C2—C3—C9—C8	2.6 (3)	C7—C8—C9—C4	−3.0 (3)
C21—C3—C9—C4	6.2 (3)	O3—C10—C11—C12	−31.7 (3)
C21—C3—C9—C8	−174.46 (17)	C13—C10—C11—C12	86.8 (3)
C2—C3—C21—C22	−95.7 (2)	C14—C10—C11—C12	−145.9 (3)
C2—C3—C21—C26	82.5 (3)	C10—C11—C12—C5	3.7 (4)
C9—C3—C21—C22	81.4 (3)	O5—C16—C17—C18	−171.3 (2)
C9—C3—C21—C26	−100.4 (2)	O5—C16—C17—C20	6.4 (3)
O3—C4—C5—C6	−179.18 (17)	C7—C16—C17—C18	9.4 (3)
O3—C4—C5—C12	−2.8 (3)	C7—C16—C17—C20	−172.87 (17)
C9—C4—C5—C6	−2.8 (3)	C16—C17—C18—C19	177.6 (2)
C9—C4—C5—C12	173.62 (19)	C20—C17—C18—C19	0.1 (3)
O3—C4—C9—C3	−0.6 (3)	C3—C21—C22—C23	−178.4 (2)
O3—C4—C9—C8	−179.93 (16)	C26—C21—C22—C23	3.4 (3)
C5—C4—C9—C3	−177.06 (18)	C3—C21—C26—C25	178.2 (2)
C5—C4—C9—C8	3.6 (3)	C22—C21—C26—C25	−3.6 (3)
C4—C5—C6—O4	176.58 (18)	C21—C22—C23—C24	−1.5 (4)
C4—C5—C6—C7	1.2 (3)	C22—C23—C24—C25	−0.3 (4)
C12—C5—C6—O4	0.4 (3)	C23—C24—C25—C26	0.0 (4)
C12—C5—C6—C7	−175.0 (2)	C24—C25—C26—C21	2.0 (4)
C4—C5—C12—C11	15.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.95	2.44	3.381 (3)	172
C26—H26···O5ⁱⁱ	0.95	2.40	3.225 (3)	145

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄O₅
M_r	416.47
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.943 (3), 11.559 (4), 12.171 (3)
α, β, γ (°)	96.238 (8), 104.041 (5), 110.301 (8)
V (Å³)	1118.7 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.50 × 0.50

Data collection
Diffractometer	Rigaku Mercury
Absorption correction	–
No. of measured, independent and observed [F² > 2σ(F²)] reflections	12333, 4480, 2706
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.092, 0.96
No. of reflections	4480
No. of parameters	304
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.31

Computer programs: CrystalClear (Rigaku, 2005), CrystalStructure (Molecular Structure Corporation & Rigaku, 2006), SIR2004 (Burla et al., 2005), CRYSTALS (Betteridge et al., 2003), X-SEED (Barbour, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.95	2.44	3.381 (3)	172
C26—H26···O5ⁱⁱ	0.95	2.40	3.225 (3)	145

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

Footnotes

‡Current address: Pharmaceutical Development, Aurigene Discovery Technologies Ltd, Miyapur, Hyderabad 500 049, India.

Acknowledgements

We thank our analytical colleagues for their support, and Drs K. Vyas & J. Moses Babu for valuable suggestions.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Carruthers, J. R. & Watkin, D. J. (1979). Acta Cryst. A35, 698–699. CrossRef CAS IUCr Journals Web of Science Google Scholar
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. Oxford University Press. Google Scholar
Molecular Structure Corporation & Rigaku (2006). CrystalStructure. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-Meth­­oxy-2,2-di­methyl-6-[(2E)-2-methyl­but-2-eno­yl]-10-phenyl-2H,8H-pyrano[2,3-f]chromen-8-one (calophyllolide)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

5-Methoxy-2,2-dimethyl-6-[(2E)-2-methylbut-2-enoyl]-10-phenyl-2H,8H-pyrano[2,3-f]chromen-8-one (calophyllolide)