Acta Cryst. (2007). E63, o3692-o3693 [ doi:10.1107/S1600536807036914 ]
The title compound, C12H12O5, isolated from the bark of Cryptocarya bracteolata, has a planar fused-ring system.
Cryptocarya bracteolata was collected in Mersing, Johor in 1997. Specimens were deposited at the Forest Research Institute of Malaysia herbarium and the Department of Chemistry, University of Malaya.
The bark of C. bracteolata (2.7 kg) was extracted with n-hexane; the solvent was then removed under vacuum. The plant material was moistened with 10% ammonium hydroxide overnight. It was extracted with dichloromethane (8 L) for 17 h to yield the crude extract (89 g). A portion (30 g) was subjected to column chromatography on silica gel 60 GF254 by using a step gradient of dichloromethane and methanol. The separation afforded 15 fractions; the second (100% dichloromethane) gave 5,6,7-trimethoxy-2H-chromen-2-one (24.5 g), whose formulation was established by spectroscopic analysis.
The carbon-bound hydrogen atoms were placed at calculated positions (C–H 0.93 to 0.98 Å) and were inlcuded in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5 Ueq(C).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
![[Figure 1]](./hb2490fig1thm.gif)
| Fig. 1. View of (I); displacement ellipsoids are drawn at the 50% probability level, and hydrogen atoms as spheres of arbitrary radius. |
| C12H12O5 | F000 = 992 |
| Mr = 236.22 | Dx = 1.399 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 11077 reflections |
| a = 13.9688 (6) Å | θ = 3.1–27.4º |
| b = 8.1164 (4) Å | µ = 0.11 mm−1 |
| c = 19.790 (1) Å | T = 295 (2) K |
| V = 2243.7 (2) Å3 | Prism, colourless |
| Z = 8 | 0.34 × 0.28 × 0.19 mm |
| Rigaku R-AXIS RAPID IP diffractometer | 2561 independent reflections |
| Radiation source: fine-focus sealed tube | 1836 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.044 |
| T = 295(2) K | θmax = 27.4º |
| ω scans | θmin = 3.1º |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −18→18 |
| Tmin = 0.738, Tmax = 0.979 | k = −10→10 |
| 19734 measured reflections | l = −25→25 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0577P)2 + 0.3525P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.118 | (Δ/σ)max = 0.001 |
| S = 1.04 | Δρmax = 0.18 e Å−3 |
| 2561 reflections | Δρmin = −0.14 e Å−3 |
| 155 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0102 (13) |
| Secondary atom site location: difference Fourier map |
| C12H12O5 | V = 2243.7 (2) Å3 |
| Mr = 236.22 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα |
| a = 13.9688 (6) Å | µ = 0.11 mm−1 |
| b = 8.1164 (4) Å | T = 295 (2) K |
| c = 19.790 (1) Å | 0.34 × 0.28 × 0.19 mm |
| Rigaku R-AXIS RAPID IP diffractometer | 2561 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1836 reflections with I > 2σ(I) |
| Tmin = 0.738, Tmax = 0.979 | Rint = 0.044 |
| 19734 measured reflections |
| R[F2 > 2σ(F2)] = 0.041 | 155 parameters |
| wR(F2) = 0.118 | H-atom parameters constrained |
| S = 1.04 | Δρmax = 0.18 e Å−3 |
| 2561 reflections | Δρmin = −0.14 e Å−3 |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.65727 (10) | 0.89131 (17) | 0.55051 (7) | 0.0721 (4) | |
| O2 | 0.61944 (7) | 0.74494 (13) | 0.46074 (5) | 0.0488 (3) | |
| O3 | 0.67995 (7) | 0.60631 (14) | 0.34306 (6) | 0.0526 (3) | |
| O4 | 0.55894 (8) | 0.41023 (14) | 0.26964 (6) | 0.0555 (3) | |
| O5 | 0.37230 (8) | 0.38596 (15) | 0.30093 (6) | 0.0603 (3) | |
| C1 | 0.59401 (13) | 0.8219 (2) | 0.52022 (8) | 0.0522 (4) | |
| C2 | 0.49443 (13) | 0.8134 (2) | 0.53901 (8) | 0.0550 (4) | |
| H2 | 0.4745 | 0.8655 | 0.5784 | 0.066* | |
| C3 | 0.42979 (12) | 0.7333 (2) | 0.50165 (8) | 0.0503 (4) | |
| H3 | 0.3660 | 0.7320 | 0.5151 | 0.060* | |
| C4 | 0.45761 (10) | 0.64940 (18) | 0.44103 (7) | 0.0412 (3) | |
| C5 | 0.55343 (10) | 0.65873 (17) | 0.42246 (7) | 0.0399 (3) | |
| C6 | 0.58711 (9) | 0.58398 (18) | 0.36371 (7) | 0.0409 (3) | |
| C7 | 0.52399 (10) | 0.49282 (18) | 0.32449 (7) | 0.0426 (4) | |
| C8 | 0.42667 (10) | 0.48059 (19) | 0.34304 (8) | 0.0447 (4) | |
| C9 | 0.39418 (10) | 0.55879 (19) | 0.40050 (8) | 0.0452 (4) | |
| H9 | 0.3299 | 0.5514 | 0.4124 | 0.054* | |
| C11 | 0.74647 (13) | 0.4929 (3) | 0.37015 (11) | 0.0789 (6) | |
| H11A | 0.8092 | 0.5169 | 0.3529 | 0.118* | |
| H11B | 0.7285 | 0.3831 | 0.3574 | 0.118* | |
| H11C | 0.7469 | 0.5018 | 0.4185 | 0.118* | |
| C12 | 0.52936 (13) | 0.4738 (3) | 0.20538 (8) | 0.0633 (5) | |
| H12A | 0.5565 | 0.4078 | 0.1700 | 0.095* | |
| H12B | 0.5510 | 0.5855 | 0.2008 | 0.095* | |
| H12C | 0.4608 | 0.4706 | 0.2024 | 0.095* | |
| C13 | 0.27263 (12) | 0.3741 (2) | 0.31493 (11) | 0.0676 (5) | |
| H13A | 0.2426 | 0.3051 | 0.2817 | 0.101* | |
| H13B | 0.2445 | 0.4820 | 0.3135 | 0.101* | |
| H13C | 0.2635 | 0.3274 | 0.3590 | 0.101* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0684 (8) | 0.0789 (9) | 0.0690 (8) | −0.0085 (7) | −0.0197 (7) | −0.0105 (7) |
| O2 | 0.0417 (6) | 0.0543 (6) | 0.0503 (6) | −0.0043 (5) | −0.0045 (5) | 0.0004 (5) |
| O3 | 0.0335 (5) | 0.0614 (7) | 0.0628 (7) | −0.0001 (5) | 0.0059 (5) | 0.0087 (6) |
| O4 | 0.0522 (6) | 0.0630 (7) | 0.0513 (6) | 0.0108 (5) | 0.0005 (5) | −0.0067 (5) |
| O5 | 0.0433 (6) | 0.0690 (8) | 0.0684 (8) | −0.0092 (5) | −0.0064 (5) | −0.0122 (6) |
| C1 | 0.0588 (10) | 0.0503 (9) | 0.0476 (9) | 0.0013 (8) | −0.0091 (8) | 0.0028 (7) |
| C2 | 0.0639 (10) | 0.0571 (9) | 0.0440 (8) | 0.0041 (8) | 0.0015 (8) | −0.0010 (8) |
| C3 | 0.0486 (8) | 0.0547 (9) | 0.0476 (8) | 0.0055 (7) | 0.0065 (7) | 0.0078 (7) |
| C4 | 0.0377 (7) | 0.0440 (8) | 0.0418 (7) | 0.0039 (6) | 0.0014 (6) | 0.0088 (6) |
| C5 | 0.0365 (7) | 0.0401 (7) | 0.0432 (8) | −0.0013 (6) | −0.0045 (6) | 0.0079 (6) |
| C6 | 0.0328 (7) | 0.0434 (8) | 0.0465 (8) | 0.0026 (6) | 0.0011 (6) | 0.0093 (6) |
| C7 | 0.0378 (7) | 0.0453 (8) | 0.0446 (8) | 0.0051 (6) | −0.0006 (6) | 0.0039 (6) |
| C8 | 0.0381 (7) | 0.0452 (8) | 0.0507 (8) | −0.0006 (6) | −0.0057 (6) | 0.0033 (7) |
| C9 | 0.0325 (7) | 0.0497 (8) | 0.0536 (9) | 0.0011 (6) | 0.0012 (6) | 0.0079 (7) |
| C11 | 0.0417 (9) | 0.0966 (15) | 0.0984 (14) | 0.0217 (10) | 0.0040 (10) | 0.0124 (13) |
| C12 | 0.0645 (11) | 0.0784 (12) | 0.0471 (9) | −0.0005 (10) | −0.0010 (8) | −0.0051 (9) |
| C13 | 0.0424 (9) | 0.0710 (12) | 0.0894 (13) | −0.0121 (8) | −0.0108 (9) | −0.0008 (10) |
| O1—C1 | 1.207 (2) | C4—C9 | 1.403 (2) |
| O2—C1 | 1.379 (2) | C5—C6 | 1.393 (2) |
| O2—C5 | 1.3834 (17) | C6—C7 | 1.388 (2) |
| O3—C6 | 1.3718 (17) | C7—C8 | 1.412 (2) |
| O3—C11 | 1.413 (2) | C8—C9 | 1.379 (2) |
| O4—C7 | 1.3661 (18) | C9—H9 | 0.9300 |
| O4—C12 | 1.433 (2) | C11—H11A | 0.9600 |
| O5—C8 | 1.3643 (18) | C11—H11B | 0.9600 |
| O5—C13 | 1.423 (2) | C11—H11C | 0.9600 |
| C1—C2 | 1.441 (2) | C12—H12A | 0.9600 |
| C2—C3 | 1.336 (2) | C12—H12B | 0.9600 |
| C2—H2 | 0.9300 | C12—H12C | 0.9600 |
| C3—C4 | 1.433 (2) | C13—H13A | 0.9600 |
| C3—H3 | 0.9300 | C13—H13B | 0.9600 |
| C4—C5 | 1.3902 (19) | C13—H13C | 0.9600 |
| C1—O2—C5 | 121.66 (12) | O5—C8—C9 | 125.42 (13) |
| C6—O3—C11 | 115.00 (13) | O5—C8—C7 | 114.64 (14) |
| C7—O4—C12 | 115.18 (12) | C9—C8—C7 | 119.93 (14) |
| C8—O5—C13 | 117.63 (13) | C8—C9—C4 | 120.31 (13) |
| O1—C1—O2 | 116.53 (16) | C8—C9—H9 | 119.8 |
| O1—C1—C2 | 126.89 (17) | C4—C9—H9 | 119.8 |
| O2—C1—C2 | 116.57 (14) | O3—C11—H11A | 109.5 |
| C3—C2—C1 | 122.18 (16) | O3—C11—H11B | 109.5 |
| C3—C2—H2 | 118.9 | H11A—C11—H11B | 109.5 |
| C1—C2—H2 | 118.9 | O3—C11—H11C | 109.5 |
| C2—C3—C4 | 120.75 (15) | H11A—C11—H11C | 109.5 |
| C2—C3—H3 | 119.6 | H11B—C11—H11C | 109.5 |
| C4—C3—H3 | 119.6 | O4—C12—H12A | 109.5 |
| C5—C4—C9 | 119.03 (14) | O4—C12—H12B | 109.5 |
| C5—C4—C3 | 117.17 (14) | H12A—C12—H12B | 109.5 |
| C9—C4—C3 | 123.80 (13) | O4—C12—H12C | 109.5 |
| O2—C5—C4 | 121.63 (13) | H12A—C12—H12C | 109.5 |
| O2—C5—C6 | 116.89 (12) | H12B—C12—H12C | 109.5 |
| C4—C5—C6 | 121.47 (13) | O5—C13—H13A | 109.5 |
| O3—C6—C7 | 120.29 (13) | O5—C13—H13B | 109.5 |
| O3—C6—C5 | 120.68 (13) | H13A—C13—H13B | 109.5 |
| C7—C6—C5 | 118.95 (13) | O5—C13—H13C | 109.5 |
| O4—C7—C6 | 118.60 (13) | H13A—C13—H13C | 109.5 |
| O4—C7—C8 | 121.09 (13) | H13B—C13—H13C | 109.5 |
| C6—C7—C8 | 120.25 (13) | ||
| C5—O2—C1—O1 | 178.68 (14) | C4—C5—C6—C7 | −2.6 (2) |
| C5—O2—C1—C2 | −2.4 (2) | C12—O4—C7—C6 | −110.92 (16) |
| O1—C1—C2—C3 | 179.80 (17) | C12—O4—C7—C8 | 71.85 (19) |
| O2—C1—C2—C3 | 1.0 (2) | O3—C6—C7—O4 | 7.7 (2) |
| C1—C2—C3—C4 | 0.9 (3) | C5—C6—C7—O4 | −175.38 (13) |
| C2—C3—C4—C5 | −1.5 (2) | O3—C6—C7—C8 | −175.06 (13) |
| C2—C3—C4—C9 | 177.99 (15) | C5—C6—C7—C8 | 1.9 (2) |
| C1—O2—C5—C4 | 1.9 (2) | C13—O5—C8—C9 | 3.9 (2) |
| C1—O2—C5—C6 | −179.19 (13) | C13—O5—C8—C7 | −177.30 (14) |
| C9—C4—C5—O2 | −179.40 (12) | O4—C7—C8—O5 | −2.0 (2) |
| C3—C4—C5—O2 | 0.1 (2) | C6—C7—C8—O5 | −179.21 (13) |
| C9—C4—C5—C6 | 1.7 (2) | O4—C7—C8—C9 | 176.87 (13) |
| C3—C4—C5—C6 | −178.74 (13) | C6—C7—C8—C9 | −0.3 (2) |
| C11—O3—C6—C7 | −95.09 (18) | O5—C8—C9—C4 | 178.20 (14) |
| C11—O3—C6—C5 | 88.04 (18) | C7—C8—C9—C4 | −0.6 (2) |
| O2—C5—C6—O3 | −4.60 (19) | C5—C4—C9—C8 | −0.1 (2) |
| C4—C5—C6—O3 | 174.30 (13) | C3—C4—C9—C8 | −179.61 (14) |
| O2—C5—C6—C7 | 178.49 (12) |
We thank Professor Gao Shan of Heilongjiang University (People's Republic of China) for the diffraction measurements. The study was supported by grants from the IndonesianTechnological and Professional Skill Development Sector Project (contract No. 465/J11/SPMU-TPSDP/2000), the University of Malaya and the French Embassy.
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6,7,8-Trimethoxycoumarin has been isolated from a wide range plants such as, for example, Acmadenia sheilae (Rutaceae) (Campbell, 1996), Artemisia adamsii (Bohlmann et al., 1985), Aralia bipinnata (Hsiao & Chiang, 1995), Baccharis species (Bohlmann et al., 1981), Bupleurum fruiticescens (Gonzalez et al., 1975), Bupleurum salicifolium (Estevez-Braun et al., 1995), Cedrelopsis grevei (Eshiett & Taylor, 1968), Cuscuta reflexa (Anis et al., 1999; Anis et al., 2002), Duranta repens (Iqbal et al., 2003), Euodia latifolia (Goh et al., 1990), Euodia (Rutaceae) (Goh et al., 1989), Euphorbia antiquorum (Sang et al., 2005), Euphorbia quinquecostata (Mbwambo et al., 1996), Fraxinus ornus (Iossifova et al., 1994), Guazuma tomentosa Kunth (Anjaneyulu & Murty, 1981), Pelargonium reniforme (Wagner, & Bladt, 1975), Picnomon acarna (Laskaris et al., 1995), Platypodium elegans (Amaral et al., 2001), Pterocaulon sphacelatum (Semple et al., 1999), Pterocaulon serrulatum (Macleod & Rasmussen, 1998), Ruta angustifolia (Del Castillo et al., 1984), Ruta angustifolia Pers (Borges del Castillo et al., 1987), Ruta oerojasme (Gonzalez et al., 1972), Ruta sp. Tene. 29662 (Gonzalez et al., 1977), Rutoideae: tribe Diosmeae (Campbell et al., 1986), Sapium chihsinianum S. Lee (Qi et al., 2004), Sapium sebiferum (Yang & Kinghorn, 1985; Shi et al., 2006), Tanacetum cilicium (Oksuz, 1990), Tanacetum heterotomum (Goren et al., 1988), Tagetes florida (Rios & Flores, 1976), Xanthoxylum inerme (Fagara boninensis) (Ishi et al., 1972), Xanthoxylum inerme Koidz. (Fagara boninensis Koidz.) (Ishii et al., 1981), Xanthoxylum integrifoliolum (Merr.) Merr. (Fagara integrifoliola Merr.) (Ishii et al., 1982), Zanthoxylum microcarpum, Zanthoxylum procerum (Boulware & Stermitz, 1981), Xanthoxylum nitidum (Roxb.) D. C. (Fagara nitida Roxb.) (Ishikawa et al., 1995), Zanthoxylum ailanthoides (Cheng et al., 2005; Shi et al., 2005), Zanthoxylum lemairie (Adesina et al., 1997), Zanthoxylum rugosum A. St. Hill & Tul (Facundo et al., 2002) and Zanthoxylum utile Huang (Ren et al., 1991). The compound (I) has been evaluated for a variety of biological activities and almost all spectrosopic analyses already have been carried out on it.
The compound has been isolated from Cryptocarya bracteolata; its crystal structure shows a planar conformation for the coumarin (Fig. 1). The compound complements the list of coumarins having methoxy (and/or hydroxy) groups in the 5 to 8 positions of the coumarin fused-ring, i.e., 6-methoxy- (Bauers et al., 2002; Gnanaguru et al., 1985), 7-methoxy- (Bhadbhade et al., 1984; Gnanaguru et al., 1984; Gnanaguru et al., 1985; Ramasubbu, et al., 1981; Ramasubbu et al., 1982), 8-methoxy- (Baures et al., 2002; Gnanaguru et al., 1985), 5,7-dimethoxy- (Ye & Fan, 2007), 7-hydroxy-6-methoxy- (Kimura et al., 1980), 7-hydroxy-5,6-dimethoxy- (Wagner et al., 1974) and 7-hydroxy-6,8-dimethoxy- (Li et al., 2001) coumarins.