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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1115.
Published online 2010 April 17. doi:  10.1107/S1600536810013577
PMCID: PMC2979159

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

Abstract

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 [triangle]). For the Chebychev polynomial used in the weighting scheme, see: Carruthers & Watkin, (1979 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1115-scheme1.jpg

Experimental

Crystal data

  • C26H24O5
  • M r = 416.47
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1115-efi1.jpg
  • 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 F 2 > 2σ(F 2)
  • R int = 0.055

Refinement

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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013577/tk2651Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

The C-bound H atoms were geometrically placed (C–H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(parent atom). A Chebychev polynomial with three parameters was used in the weighting scheme, see: Carruthers & Watkin, 1979)

Figures

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..

Crystal data

C26H24O5Z = 2
Mr = 416.47F(000) = 440.00
Triclinic, P1Dx = 1.236 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 8.943 (3) ÅCell parameters from 4735 reflections
b = 11.559 (4) Åθ = 2.5–27.4°
c = 12.171 (3) ŵ = 0.09 mm1
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

Rigaku Mercury diffractometerRint = 0.055
Detector resolution: 7.31 pixels mm-1θmax = 27.4°
ω scansh = −11→11
12333 measured reflectionsk = −14→11
4480 independent reflectionsl = −15→15
2706 reflections with F2 > 2σ(F2)

Refinement

Refinement on F2H-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 = 0.96Δρmax = 0.34 e Å3
4480 reflectionsΔρmin = −0.31 e Å3
304 parameters

Special details

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)

xyzUiso*/Ueq
O10.76337 (17)1.04526 (10)0.54924 (11)0.0565 (4)
O20.6788 (2)1.17903 (13)0.46095 (14)0.0901 (7)
O30.61388 (16)0.61390 (10)0.36909 (10)0.0549 (4)
O40.97605 (19)0.78784 (14)0.75890 (11)0.0674 (5)
O51.1027 (2)1.10050 (18)0.75198 (16)0.1159 (8)
C10.6716 (2)1.07075 (17)0.45404 (18)0.0615 (7)
C20.5705 (2)0.96723 (17)0.35769 (17)0.0598 (7)
C30.5714 (2)0.85017 (16)0.35387 (15)0.0478 (5)
C40.7000 (2)0.71305 (14)0.46131 (14)0.0454 (5)
C50.7989 (2)0.69796 (16)0.56201 (15)0.0508 (5)
C60.8849 (2)0.80206 (17)0.65664 (15)0.0519 (6)
C70.8693 (2)0.91656 (15)0.65085 (15)0.0484 (5)
C80.7687 (2)0.92695 (14)0.54971 (15)0.0449 (5)
C90.6773 (2)0.82733 (14)0.45266 (13)0.0417 (5)
C100.6832 (2)0.51684 (16)0.35424 (17)0.0589 (6)
C110.7414 (3)0.48607 (17)0.4694 (2)0.0740 (8)
C120.8001 (3)0.57273 (18)0.56640 (19)0.0688 (8)
C130.8261 (3)0.5703 (2)0.3035 (2)0.0845 (10)
C140.5371 (3)0.40608 (18)0.2700 (2)0.0821 (9)
C151.1373 (3)0.7892 (2)0.7603 (2)0.0913 (10)
C160.9666 (2)1.02968 (17)0.75119 (16)0.0569 (6)
C170.8941 (2)1.05157 (16)0.84342 (15)0.0540 (6)
C180.7537 (2)0.9633 (2)0.84800 (17)0.0637 (7)
C190.6672 (3)0.9685 (3)0.9381 (2)0.1058 (11)
C200.9897 (3)1.1736 (2)0.9313 (2)0.0908 (9)
C210.4565 (2)0.74887 (17)0.24960 (15)0.0530 (5)
C220.3021 (2)0.6686 (2)0.25190 (19)0.0747 (8)
C230.1968 (3)0.5724 (2)0.1561 (2)0.0879 (9)
C240.2434 (3)0.5585 (2)0.0590 (2)0.0906 (9)
C250.3941 (3)0.6396 (2)0.0550 (2)0.1014 (10)
C260.5003 (3)0.7362 (2)0.14927 (19)0.0842 (9)
H20.500800.981900.292900.0750*
H110.734700.402800.472800.0930*
H120.843500.553500.638200.0880*
H180.704300.889000.788600.0790*
H220.267600.678400.319100.0850*
H230.091200.516100.157900.0930*
H240.172100.49190−0.005600.0950*
H250.424100.63110−0.014300.1080*
H260.604900.792100.145500.0910*
H1310.907700.535900.328500.1110*
H1320.875800.659600.328700.1110*
H1330.783700.548800.221400.1110*
H1410.476500.354200.312700.0950*
H1420.576300.358100.224300.0940*
H1430.466100.436600.221000.0950*
H1511.126600.705300.734900.1170*
H1521.213700.822600.836300.1170*
H1531.177700.839800.709100.1170*
H1910.550500.921500.904900.1330*
H1920.709400.934401.000400.1340*
H1930.686901.054100.966100.1340*
H2010.915101.201100.959800.1020*
H2021.066101.161300.993700.1020*
H2031.049701.235600.895700.1020*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0749 (8)0.0356 (5)0.0624 (7)0.0231 (5)0.0257 (6)0.0064 (5)
O20.1485 (16)0.0520 (8)0.0941 (12)0.0577 (9)0.0467 (11)0.0257 (7)
O30.0728 (8)0.0364 (6)0.0526 (7)0.0220 (5)0.0166 (6)0.0006 (5)
O40.0794 (9)0.0817 (9)0.0477 (7)0.0397 (8)0.0165 (6)0.0176 (6)
O50.0764 (11)0.1121 (14)0.1056 (14)−0.0198 (10)0.0414 (10)−0.0323 (11)
C10.0890 (14)0.0468 (10)0.0662 (12)0.0374 (10)0.0333 (11)0.0212 (9)
C20.0729 (13)0.0520 (10)0.0637 (12)0.0328 (9)0.0215 (10)0.0180 (9)
C30.0525 (9)0.0482 (9)0.0495 (9)0.0226 (8)0.0214 (7)0.0137 (7)
C40.0584 (10)0.0343 (7)0.0465 (9)0.0180 (7)0.0216 (7)0.0068 (6)
C50.0688 (11)0.0441 (8)0.0489 (9)0.0269 (8)0.0256 (8)0.0124 (7)
C60.0617 (11)0.0575 (10)0.0430 (9)0.0266 (8)0.0207 (8)0.0140 (7)
C70.0533 (10)0.0438 (8)0.0486 (9)0.0175 (7)0.0196 (7)0.0060 (7)
C80.0539 (9)0.0328 (7)0.0514 (9)0.0179 (7)0.0214 (8)0.0055 (6)
C90.0520 (9)0.0362 (7)0.0413 (8)0.0194 (7)0.0183 (7)0.0086 (6)
C100.0787 (13)0.0371 (8)0.0656 (12)0.0253 (8)0.0287 (10)0.0042 (7)
C110.1114 (18)0.0362 (9)0.0839 (15)0.0360 (11)0.0336 (13)0.0157 (9)
C120.1012 (16)0.0529 (10)0.0658 (13)0.0406 (11)0.0283 (12)0.0234 (9)
C130.1012 (18)0.0680 (13)0.1079 (19)0.0420 (13)0.0576 (16)0.0221 (12)
C140.0934 (17)0.0468 (11)0.0952 (17)0.0213 (11)0.0294 (13)−0.0107 (10)
C150.0966 (18)0.119 (2)0.0764 (16)0.0670 (17)0.0208 (13)0.0192 (14)
C160.0543 (11)0.0483 (9)0.0573 (11)0.0117 (8)0.0144 (8)0.0015 (8)
C170.0714 (12)0.0495 (9)0.0412 (9)0.0298 (9)0.0105 (8)0.0034 (7)
C180.0734 (13)0.0721 (12)0.0526 (11)0.0333 (11)0.0244 (9)0.0116 (9)
C190.114 (2)0.148 (2)0.0715 (16)0.055 (2)0.0482 (16)0.0263 (16)
C200.122 (2)0.0685 (14)0.0641 (14)0.0308 (14)0.0172 (13)−0.0123 (11)
C210.0577 (10)0.0509 (9)0.0486 (9)0.0192 (8)0.0136 (8)0.0150 (7)
C220.0653 (13)0.0826 (14)0.0635 (13)0.0144 (11)0.0186 (10)0.0149 (11)
C230.0701 (15)0.0864 (16)0.0759 (15)0.0031 (12)0.0088 (12)0.0147 (13)
C240.0828 (17)0.0856 (17)0.0683 (15)0.0129 (14)−0.0020 (13)−0.0004 (13)
C250.0934 (19)0.120 (2)0.0559 (13)0.0087 (16)0.0222 (13)−0.0095 (14)
C260.0747 (15)0.0923 (17)0.0604 (13)0.0053 (13)0.0248 (11)−0.0031 (12)

Geometric parameters (Å, °)

O1—C11.372 (2)C21—C261.378 (3)
O1—C81.385 (2)C22—C231.393 (3)
O2—C11.223 (2)C23—C241.357 (4)
O3—C41.362 (2)C24—C251.365 (4)
O3—C101.473 (2)C25—C261.386 (3)
O4—C61.373 (2)C2—H20.9500
O4—C151.433 (3)C11—H110.9500
O5—C161.205 (3)C12—H120.9500
C1—C21.433 (3)C13—H1310.9500
C2—C31.352 (3)C13—H1320.9500
C3—C91.450 (2)C13—H1330.9500
C3—C211.499 (3)C14—H1410.9500
C4—C51.394 (2)C14—H1420.9500
C4—C91.415 (2)C14—H1430.9500
C5—C61.412 (3)C15—H1510.9500
C5—C121.458 (3)C15—H1520.9500
C6—C71.386 (3)C15—H1530.9500
C7—C81.382 (3)C18—H180.9500
C7—C161.519 (3)C19—H1910.9500
C8—C91.404 (2)C19—H1920.9500
C10—C111.498 (3)C19—H1930.9500
C10—C131.521 (3)C20—H2010.9500
C10—C141.517 (3)C20—H2020.9500
C11—C121.323 (3)C20—H2030.9500
C16—C171.466 (3)C22—H220.9500
C17—C181.333 (3)C23—H230.9500
C17—C201.502 (3)C24—H240.9500
C18—C191.495 (3)C25—H250.9500
C21—C221.380 (3)C26—H260.9500
C1—O1—C8121.76 (14)C21—C26—C25120.1 (2)
C4—O3—C10117.74 (14)C1—C2—H2118.00
C6—O4—C15115.00 (16)C3—C2—H2118.00
O1—C1—O2116.84 (18)C10—C11—H11119.00
O1—C1—C2117.20 (16)C12—C11—H11120.00
O2—C1—C2125.90 (19)C5—C12—H12120.00
C1—C2—C3123.13 (18)C11—C12—H12120.00
C2—C3—C9118.60 (16)C10—C13—H131110.00
C2—C3—C21118.10 (17)C10—C13—H132110.00
C9—C3—C21123.24 (15)C10—C13—H133109.00
O3—C4—C5120.05 (15)H131—C13—H132109.00
O3—C4—C9117.64 (15)H131—C13—H133110.00
C5—C4—C9122.22 (15)H132—C13—H133109.00
C4—C5—C6118.71 (16)C10—C14—H141109.00
C4—C5—C12117.92 (16)C10—C14—H142110.00
C6—C5—C12123.27 (17)C10—C14—H143109.00
O4—C6—C5119.82 (17)H141—C14—H142109.00
O4—C6—C7119.10 (16)H141—C14—H143109.00
C5—C6—C7120.92 (16)H142—C14—H143110.00
C6—C7—C8118.42 (16)O4—C15—H151109.00
C6—C7—C16120.80 (16)O4—C15—H152111.00
C8—C7—C16120.72 (15)O4—C15—H153109.00
O1—C8—C7115.05 (15)H151—C15—H152109.00
O1—C8—C9120.94 (15)H151—C15—H153110.00
C7—C8—C9124.01 (15)H152—C15—H153109.00
C3—C9—C4126.22 (15)C17—C18—H18117.00
C3—C9—C8118.14 (15)C19—C18—H18117.00
C4—C9—C8115.64 (15)C18—C19—H191110.00
O3—C10—C11109.14 (16)C18—C19—H192110.00
O3—C10—C13107.16 (15)C18—C19—H193109.00
O3—C10—C14103.60 (16)H191—C19—H192110.00
C11—C10—C13111.86 (19)H191—C19—H193109.00
C11—C10—C14112.31 (16)H192—C19—H193109.00
C13—C10—C14112.28 (18)C17—C20—H201110.00
C10—C11—C12121.01 (18)C17—C20—H202109.00
C5—C12—C11119.6 (2)C17—C20—H203109.00
O5—C16—C7118.35 (18)H201—C20—H202110.00
O5—C16—C17121.52 (18)H201—C20—H203109.00
C7—C16—C17120.12 (16)H202—C20—H203109.00
C16—C17—C18119.84 (17)C21—C22—H22120.00
C16—C17—C20116.41 (18)C23—C22—H22120.00
C18—C17—C20123.71 (19)C22—C23—H23120.00
C17—C18—C19126.6 (2)C24—C23—H23119.00
C3—C21—C22120.04 (17)C23—C24—H24120.00
C3—C21—C26121.08 (18)C25—C24—H24120.00
C22—C21—C26118.86 (19)C24—C25—H25119.00
C21—C22—C23120.1 (2)C26—C25—H25120.00
C22—C23—C24120.4 (2)C21—C26—H26120.00
C23—C24—C25119.8 (2)C25—C26—H26120.00
C24—C25—C26120.7 (2)
C8—O1—C1—O2−177.92 (18)C6—C5—C12—C11−168.4 (2)
C8—O1—C1—C24.8 (3)O4—C6—C7—C8−176.02 (18)
C1—O1—C8—C7178.65 (17)O4—C6—C7—C166.7 (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—C9155.07 (16)C6—C7—C8—O1−178.13 (17)
C4—O3—C10—C1143.8 (2)C6—C7—C8—C91.6 (3)
C4—O3—C10—C13−77.49 (19)C16—C7—C8—O1−0.9 (3)
C4—O3—C10—C14163.64 (15)C16—C7—C8—C9178.89 (18)
C15—O4—C6—C579.4 (2)C6—C7—C16—O590.6 (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—C3178.1 (2)C8—C7—C16—C1792.8 (2)
C1—C2—C3—C91.1 (3)O1—C8—C9—C3−2.7 (3)
C1—C2—C3—C21178.37 (18)O1—C8—C9—C4176.71 (16)
C2—C3—C9—C4−176.70 (19)C7—C8—C9—C3177.57 (18)
C2—C3—C9—C82.6 (3)C7—C8—C9—C4−3.0 (3)
C21—C3—C9—C46.2 (3)O3—C10—C11—C12−31.7 (3)
C21—C3—C9—C8−174.46 (17)C13—C10—C11—C1286.8 (3)
C2—C3—C21—C22−95.7 (2)C14—C10—C11—C12−145.9 (3)
C2—C3—C21—C2682.5 (3)C10—C11—C12—C53.7 (4)
C9—C3—C21—C2281.4 (3)O5—C16—C17—C18−171.3 (2)
C9—C3—C21—C26−100.4 (2)O5—C16—C17—C206.4 (3)
O3—C4—C5—C6−179.18 (17)C7—C16—C17—C189.4 (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—C19177.6 (2)
C9—C4—C5—C12173.62 (19)C20—C17—C18—C190.1 (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—C233.4 (3)
C5—C4—C9—C3−177.06 (18)C3—C21—C26—C25178.2 (2)
C5—C4—C9—C83.6 (3)C22—C21—C26—C25−3.6 (3)
C4—C5—C6—O4176.58 (18)C21—C22—C23—C24−1.5 (4)
C4—C5—C6—C71.2 (3)C22—C23—C24—C25−0.3 (4)
C12—C5—C6—O40.4 (3)C23—C24—C25—C260.0 (4)
C12—C5—C6—C7−175.0 (2)C24—C25—C26—C212.0 (4)
C4—C5—C12—C1115.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C11—H11···O2i0.952.443.381 (3)172
C26—H26···O5ii0.952.403.225 (3)145

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2651).

References

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Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography