Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042303/ci6734sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042303/ci6734Isup2.hkl |
CCDC reference: 296718
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.140
- Data-to-parameter ratio = 19.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Air-dried roots of C. formosum ssp. pruniflorum (4 kg) were ground and extracted with hexane and CH2Cl2 (2 × 20 l for each solvent) for 5 d at room temperature. The residue obtained after evaporation of the solvent was subjected to quick column chromatography over silica gel and eluted with a gradient of EtOAc–hexane to afford ten fractions (F1–F10). Fraction F2 was separated by column chromatography (CC) and eluted with 100% CH2Cl2 to afford four fractions (2 A–two-dimensional). Fraction 2 A was further purified by CC with 30% EtOAc–hexane to give compound (I). Compound (I) was recrystallized from CHCl3–CH3OH (4:1 v/v) to yield, after several days, yellow needle-shaped single-crystals (m.p. 445–447 K).
Atom H1O4 was located in a difference map and refined isotropically. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with O—H = 0.82 Å and C—H = 0.93–0.97 Å. The Uiso(H) values were constrained to be 1.5Ueq of the carrier atom for hydroxyl and methyl H atoms, and 1.2Ueq for the remaining H atoms.
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C25H28O6 | Z = 2 |
Mr = 424.27 | F(000) = 452 |
Triclinic, P1 | Dx = 1.309 Mg m−3 |
Hall symbol: -P 1 | Melting point = 445–447 K |
a = 7.8938 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.1976 (1) Å | Cell parameters from 5720 reflections |
c = 13.7937 (2) Å | θ = 1.5–29.0° |
α = 79.311 (1)° | µ = 0.09 mm−1 |
β = 80.926 (1)° | T = 100 K |
γ = 87.850 (1)° | Needle, yellow |
V = 1077.40 (2) Å3 | 0.50 × 0.28 × 0.23 mm |
Bruker SMART APEX2 CCD area-detector diffractometer | 5720 independent reflections |
Radiation source: fine-focus sealed tube | 4623 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 8.33 pixels mm-1 | θmax = 29.0°, θmin = 1.5° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −13→13 |
Tmin = 0.969, Tmax = 0.979 | l = −18→18 |
16706 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0749P)2 + 0.1769P] where P = (Fo2 + 2Fc2)/3 |
5720 reflections | (Δ/σ)max = 0.001 |
291 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C25H28O6 | γ = 87.850 (1)° |
Mr = 424.27 | V = 1077.40 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.8938 (1) Å | Mo Kα radiation |
b = 10.1976 (1) Å | µ = 0.09 mm−1 |
c = 13.7937 (2) Å | T = 100 K |
α = 79.311 (1)° | 0.50 × 0.28 × 0.23 mm |
β = 80.926 (1)° |
Bruker SMART APEX2 CCD area-detector diffractometer | 5720 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 4623 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.979 | Rint = 0.018 |
16706 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.30 e Å−3 |
5720 reflections | Δρmin = −0.21 e Å−3 |
291 parameters |
Experimental. The data were collected with the Oxford Cyrosystem Cobra low-temperature attachment |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.56817 (13) | 0.26595 (9) | 0.33464 (7) | 0.0476 (2) | |
H1O1 | 0.5492 | 0.3111 | 0.3786 | 0.071* | |
O2 | 0.56808 (13) | 0.32975 (9) | 0.50530 (7) | 0.0502 (2) | |
O3 | 0.78715 (11) | −0.03314 (8) | 0.59857 (6) | 0.03704 (19) | |
O4 | 0.78030 (14) | 0.03519 (10) | 0.92394 (7) | 0.0510 (3) | |
H1O4 | 0.753 (3) | 0.096 (2) | 0.9588 (17) | 0.093 (7)* | |
O5 | 0.63229 (11) | 0.27839 (9) | 0.88553 (6) | 0.0429 (2) | |
O6 | 0.78391 (12) | −0.15344 (9) | 0.28254 (7) | 0.0458 (2) | |
C1 | 0.64106 (14) | 0.14889 (11) | 0.37044 (8) | 0.0334 (2) | |
C2 | 0.67944 (14) | 0.05629 (11) | 0.30825 (8) | 0.0340 (2) | |
C3 | 0.75272 (14) | −0.06629 (11) | 0.34706 (8) | 0.0347 (2) | |
C4 | 0.78828 (15) | −0.09603 (11) | 0.44443 (8) | 0.0360 (2) | |
H4 | 0.8363 | −0.1778 | 0.4689 | 0.043* | |
C5 | 0.74976 (14) | 0.00012 (11) | 0.50364 (8) | 0.0318 (2) | |
C6 | 0.67570 (14) | 0.12306 (10) | 0.47054 (8) | 0.0314 (2) | |
C7 | 0.63607 (14) | 0.22030 (11) | 0.53537 (8) | 0.0336 (2) | |
C8 | 0.67746 (13) | 0.18158 (10) | 0.63669 (8) | 0.0310 (2) | |
C9 | 0.74985 (14) | 0.05417 (11) | 0.66330 (8) | 0.0319 (2) | |
C10 | 0.79042 (15) | 0.00587 (11) | 0.75780 (8) | 0.0367 (2) | |
H10 | 0.8449 | −0.0764 | 0.7719 | 0.044* | |
C11 | 0.74791 (15) | 0.08299 (12) | 0.83007 (8) | 0.0364 (2) | |
C12 | 0.67072 (14) | 0.20900 (11) | 0.80712 (8) | 0.0341 (2) | |
C13 | 0.64127 (13) | 0.26295 (11) | 0.71148 (8) | 0.0322 (2) | |
C14 | 0.58846 (15) | 0.40903 (11) | 0.68901 (9) | 0.0372 (2) | |
H14A | 0.5023 | 0.4203 | 0.6451 | 0.045* | |
H14B | 0.5395 | 0.4386 | 0.7504 | 0.045* | |
C15 | 0.74385 (16) | 0.49067 (11) | 0.63991 (9) | 0.0403 (3) | |
H15 | 0.7817 | 0.4874 | 0.5730 | 0.048* | |
C16 | 0.83292 (17) | 0.56687 (12) | 0.68156 (11) | 0.0458 (3) | |
C17 | 0.9924 (2) | 0.63696 (16) | 0.62400 (16) | 0.0701 (5) | |
H17A | 1.0084 | 0.6217 | 0.5565 | 0.105* | |
H17B | 1.0898 | 0.6028 | 0.6548 | 0.105* | |
H17C | 0.9806 | 0.7310 | 0.6240 | 0.105* | |
C18 | 0.7855 (3) | 0.5911 (2) | 0.78640 (13) | 0.0748 (5) | |
H18A | 0.6985 | 0.5292 | 0.8219 | 0.112* | |
H18B | 0.7426 | 0.6807 | 0.7852 | 0.112* | |
H18C | 0.8850 | 0.5790 | 0.8193 | 0.112* | |
C19 | 0.4588 (2) | 0.25895 (19) | 0.93526 (12) | 0.0634 (4) | |
H19A | 0.4355 | 0.3149 | 0.9847 | 0.095* | |
H19B | 0.4433 | 0.1672 | 0.9669 | 0.095* | |
H19C | 0.3816 | 0.2818 | 0.8874 | 0.095* | |
C20 | 0.8581 (2) | −0.27955 (14) | 0.31634 (11) | 0.0526 (3) | |
H20A | 0.8701 | −0.3317 | 0.2644 | 0.079* | |
H20B | 0.7854 | −0.3254 | 0.3742 | 0.079* | |
H20C | 0.9689 | −0.2667 | 0.3333 | 0.079* | |
C21 | 0.64444 (15) | 0.08650 (12) | 0.20152 (8) | 0.0378 (2) | |
H21A | 0.5971 | 0.0078 | 0.1859 | 0.045* | |
H21B | 0.5593 | 0.1574 | 0.1952 | 0.045* | |
C22 | 0.80319 (16) | 0.12797 (13) | 0.12721 (8) | 0.0392 (3) | |
H22 | 0.8811 | 0.0604 | 0.1141 | 0.047* | |
C23 | 0.84422 (17) | 0.25062 (14) | 0.07827 (9) | 0.0446 (3) | |
C24 | 1.0069 (2) | 0.27493 (18) | 0.00411 (12) | 0.0635 (4) | |
H24A | 1.0698 | 0.1926 | 0.0032 | 0.095* | |
H24B | 1.0757 | 0.3388 | 0.0230 | 0.095* | |
H24C | 0.9787 | 0.3088 | −0.0612 | 0.095* | |
C25 | 0.7399 (2) | 0.37381 (15) | 0.09134 (12) | 0.0612 (4) | |
H25A | 0.6351 | 0.3494 | 0.1358 | 0.092* | |
H25B | 0.7139 | 0.4186 | 0.0277 | 0.092* | |
H25C | 0.8040 | 0.4323 | 0.1188 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0666 (6) | 0.0390 (5) | 0.0400 (4) | 0.0147 (4) | −0.0180 (4) | −0.0089 (4) |
O2 | 0.0737 (7) | 0.0352 (5) | 0.0473 (5) | 0.0175 (4) | −0.0243 (5) | −0.0132 (4) |
O3 | 0.0483 (5) | 0.0312 (4) | 0.0346 (4) | 0.0075 (3) | −0.0122 (3) | −0.0102 (3) |
O4 | 0.0758 (7) | 0.0458 (5) | 0.0335 (4) | 0.0075 (5) | −0.0161 (4) | −0.0079 (4) |
O5 | 0.0478 (5) | 0.0472 (5) | 0.0367 (4) | −0.0008 (4) | −0.0032 (4) | −0.0178 (4) |
O6 | 0.0559 (5) | 0.0439 (5) | 0.0427 (5) | 0.0091 (4) | −0.0109 (4) | −0.0202 (4) |
C1 | 0.0345 (5) | 0.0323 (5) | 0.0334 (5) | −0.0003 (4) | −0.0060 (4) | −0.0055 (4) |
C2 | 0.0330 (5) | 0.0373 (6) | 0.0324 (5) | −0.0029 (4) | −0.0045 (4) | −0.0080 (4) |
C3 | 0.0337 (5) | 0.0366 (5) | 0.0360 (5) | −0.0013 (4) | −0.0033 (4) | −0.0134 (4) |
C4 | 0.0398 (6) | 0.0315 (5) | 0.0385 (5) | 0.0051 (4) | −0.0076 (5) | −0.0104 (4) |
C5 | 0.0320 (5) | 0.0320 (5) | 0.0322 (5) | −0.0008 (4) | −0.0057 (4) | −0.0073 (4) |
C6 | 0.0328 (5) | 0.0300 (5) | 0.0325 (5) | −0.0007 (4) | −0.0058 (4) | −0.0078 (4) |
C7 | 0.0363 (5) | 0.0298 (5) | 0.0363 (5) | 0.0010 (4) | −0.0080 (4) | −0.0081 (4) |
C8 | 0.0313 (5) | 0.0297 (5) | 0.0334 (5) | −0.0004 (4) | −0.0059 (4) | −0.0083 (4) |
C9 | 0.0328 (5) | 0.0296 (5) | 0.0346 (5) | −0.0003 (4) | −0.0055 (4) | −0.0092 (4) |
C10 | 0.0425 (6) | 0.0318 (5) | 0.0368 (5) | 0.0026 (4) | −0.0100 (5) | −0.0064 (4) |
C11 | 0.0402 (6) | 0.0377 (6) | 0.0322 (5) | −0.0037 (4) | −0.0071 (4) | −0.0066 (4) |
C12 | 0.0341 (5) | 0.0353 (5) | 0.0347 (5) | −0.0031 (4) | −0.0033 (4) | −0.0120 (4) |
C13 | 0.0288 (5) | 0.0323 (5) | 0.0371 (5) | −0.0010 (4) | −0.0045 (4) | −0.0106 (4) |
C14 | 0.0388 (6) | 0.0338 (5) | 0.0422 (6) | 0.0059 (4) | −0.0087 (5) | −0.0140 (4) |
C15 | 0.0479 (7) | 0.0301 (5) | 0.0426 (6) | 0.0043 (5) | −0.0037 (5) | −0.0092 (4) |
C16 | 0.0453 (7) | 0.0333 (6) | 0.0588 (8) | 0.0013 (5) | −0.0135 (6) | −0.0034 (5) |
C17 | 0.0550 (9) | 0.0444 (8) | 0.1042 (14) | −0.0088 (7) | −0.0070 (9) | 0.0009 (8) |
C18 | 0.0985 (14) | 0.0741 (11) | 0.0615 (10) | −0.0284 (10) | −0.0253 (9) | −0.0210 (8) |
C19 | 0.0572 (9) | 0.0776 (11) | 0.0538 (8) | −0.0012 (8) | 0.0113 (7) | −0.0247 (8) |
C20 | 0.0613 (8) | 0.0436 (7) | 0.0587 (8) | 0.0121 (6) | −0.0116 (7) | −0.0246 (6) |
C21 | 0.0381 (6) | 0.0438 (6) | 0.0339 (5) | −0.0022 (5) | −0.0085 (4) | −0.0104 (4) |
C22 | 0.0410 (6) | 0.0463 (6) | 0.0316 (5) | 0.0022 (5) | −0.0070 (4) | −0.0099 (5) |
C23 | 0.0470 (7) | 0.0507 (7) | 0.0367 (6) | −0.0043 (5) | −0.0069 (5) | −0.0086 (5) |
C24 | 0.0582 (9) | 0.0731 (10) | 0.0523 (8) | −0.0146 (8) | 0.0031 (7) | −0.0003 (7) |
C25 | 0.0781 (11) | 0.0452 (8) | 0.0587 (9) | −0.0021 (7) | −0.0056 (8) | −0.0091 (6) |
O1—C1 | 1.3489 (13) | C14—H14B | 0.97 |
O1—H1O1 | 0.82 | C15—C16 | 1.3274 (18) |
O2—C7 | 1.2488 (13) | C15—H15 | 0.93 |
O3—C5 | 1.3663 (13) | C16—C18 | 1.499 (2) |
O3—C9 | 1.3670 (12) | C16—C17 | 1.506 (2) |
O4—C11 | 1.3566 (14) | C17—H17A | 0.96 |
O4—H1O4 | 0.85 (2) | C17—H17B | 0.96 |
O5—C12 | 1.3881 (13) | C17—H17C | 0.96 |
O5—C19 | 1.4348 (18) | C18—H18A | 0.96 |
O6—C3 | 1.3602 (13) | C18—H18B | 0.96 |
O6—C20 | 1.4217 (16) | C18—H18C | 0.96 |
C1—C2 | 1.3844 (15) | C19—H19A | 0.96 |
C1—C6 | 1.4246 (15) | C19—H19B | 0.96 |
C2—C3 | 1.4067 (16) | C19—H19C | 0.96 |
C2—C21 | 1.5140 (15) | C20—H20A | 0.96 |
C3—C4 | 1.3914 (16) | C20—H20B | 0.96 |
C4—C5 | 1.3846 (15) | C20—H20C | 0.96 |
C4—H4 | 0.93 | C21—C22 | 1.5078 (17) |
C5—C6 | 1.3924 (15) | C21—H21A | 0.97 |
C6—C7 | 1.4484 (14) | C21—H21B | 0.97 |
C7—C8 | 1.4647 (15) | C22—C23 | 1.3316 (18) |
C8—C9 | 1.4081 (14) | C22—H22 | 0.93 |
C8—C13 | 1.4288 (14) | C23—C25 | 1.499 (2) |
C9—C10 | 1.3878 (15) | C23—C24 | 1.5074 (19) |
C10—C11 | 1.3749 (16) | C24—H24A | 0.96 |
C10—H10 | 0.93 | C24—H24B | 0.96 |
C11—C12 | 1.4049 (16) | C24—H24C | 0.96 |
C12—C13 | 1.3838 (15) | C25—H25A | 0.96 |
C13—C14 | 1.5205 (15) | C25—H25B | 0.96 |
C14—C15 | 1.5039 (17) | C25—H25C | 0.96 |
C14—H14A | 0.97 | ||
C1—O1—H1O1 | 109.5 | C14—C15—H15 | 116.4 |
C5—O3—C9 | 120.03 (8) | C15—C16—C18 | 124.13 (13) |
C11—O4—H1O4 | 107.9 (15) | C15—C16—C17 | 120.94 (14) |
C12—O5—C19 | 112.64 (10) | C18—C16—C17 | 114.93 (14) |
C3—O6—C20 | 118.14 (10) | C16—C17—H17A | 109.5 |
O1—C1—C2 | 118.57 (10) | C16—C17—H17B | 109.5 |
O1—C1—C6 | 119.72 (10) | H17A—C17—H17B | 109.5 |
C2—C1—C6 | 121.71 (10) | C16—C17—H17C | 109.5 |
C1—C2—C3 | 118.00 (10) | H17A—C17—H17C | 109.5 |
C1—C2—C21 | 120.94 (10) | H17B—C17—H17C | 109.5 |
C3—C2—C21 | 121.07 (10) | C16—C18—H18A | 109.5 |
O6—C3—C4 | 122.87 (10) | C16—C18—H18B | 109.5 |
O6—C3—C2 | 114.84 (10) | H18A—C18—H18B | 109.5 |
C4—C3—C2 | 122.28 (10) | C16—C18—H18C | 109.5 |
C5—C4—C3 | 117.78 (10) | H18A—C18—H18C | 109.5 |
C5—C4—H4 | 121.1 | H18B—C18—H18C | 109.5 |
C3—C4—H4 | 121.1 | O5—C19—H19A | 109.5 |
O3—C5—C4 | 115.82 (9) | O5—C19—H19B | 109.5 |
O3—C5—C6 | 121.11 (9) | H19A—C19—H19B | 109.5 |
C4—C5—C6 | 123.07 (10) | O5—C19—H19C | 109.5 |
C5—C6—C1 | 117.16 (10) | H19A—C19—H19C | 109.5 |
C5—C6—C7 | 121.22 (9) | H19B—C19—H19C | 109.5 |
C1—C6—C7 | 121.62 (9) | O6—C20—H20A | 109.5 |
O2—C7—C6 | 120.73 (10) | O6—C20—H20B | 109.5 |
O2—C7—C8 | 122.92 (10) | H20A—C20—H20B | 109.5 |
C6—C7—C8 | 116.34 (9) | O6—C20—H20C | 109.5 |
C9—C8—C13 | 118.07 (9) | H20A—C20—H20C | 109.5 |
C9—C8—C7 | 118.04 (9) | H20B—C20—H20C | 109.5 |
C13—C8—C7 | 123.83 (9) | C22—C21—C2 | 112.75 (9) |
O3—C9—C10 | 113.79 (9) | C22—C21—H21A | 109.0 |
O3—C9—C8 | 123.23 (9) | C2—C21—H21A | 109.0 |
C10—C9—C8 | 122.97 (10) | C22—C21—H21B | 109.0 |
C11—C10—C9 | 118.17 (10) | C2—C21—H21B | 109.0 |
C11—C10—H10 | 120.9 | H21A—C21—H21B | 107.8 |
C9—C10—H10 | 120.9 | C23—C22—C21 | 127.21 (12) |
O4—C11—C10 | 119.05 (10) | C23—C22—H22 | 116.4 |
O4—C11—C12 | 120.54 (10) | C21—C22—H22 | 116.4 |
C10—C11—C12 | 120.40 (10) | C22—C23—C25 | 124.85 (13) |
C13—C12—O5 | 122.03 (10) | C22—C23—C24 | 120.62 (13) |
C13—C12—C11 | 122.14 (10) | C25—C23—C24 | 114.52 (13) |
O5—C12—C11 | 115.78 (10) | C23—C24—H24A | 109.5 |
C12—C13—C8 | 117.97 (10) | C23—C24—H24B | 109.5 |
C12—C13—C14 | 118.56 (10) | H24A—C24—H24B | 109.5 |
C8—C13—C14 | 123.21 (10) | C23—C24—H24C | 109.5 |
C15—C14—C13 | 108.98 (9) | H24A—C24—H24C | 109.5 |
C15—C14—H14A | 109.9 | H24B—C24—H24C | 109.5 |
C13—C14—H14A | 109.9 | C23—C25—H25A | 109.5 |
C15—C14—H14B | 109.9 | C23—C25—H25B | 109.5 |
C13—C14—H14B | 109.9 | H25A—C25—H25B | 109.5 |
H14A—C14—H14B | 108.3 | C23—C25—H25C | 109.5 |
C16—C15—C14 | 127.13 (12) | H25A—C25—H25C | 109.5 |
C16—C15—H15 | 116.4 | H25B—C25—H25C | 109.5 |
O1—C1—C2—C3 | −178.93 (10) | C5—O3—C9—C8 | −1.87 (16) |
C6—C1—C2—C3 | 0.71 (17) | C13—C8—C9—O3 | 178.85 (9) |
O1—C1—C2—C21 | 1.41 (17) | C7—C8—C9—O3 | 1.74 (16) |
C6—C1—C2—C21 | −178.95 (10) | C13—C8—C9—C10 | −1.36 (17) |
C20—O6—C3—C4 | −0.80 (18) | C7—C8—C9—C10 | −178.47 (10) |
C20—O6—C3—C2 | 179.94 (11) | O3—C9—C10—C11 | −176.04 (10) |
C1—C2—C3—O6 | 178.76 (10) | C8—C9—C10—C11 | 4.15 (18) |
C21—C2—C3—O6 | −1.58 (16) | C9—C10—C11—O4 | 177.40 (11) |
C1—C2—C3—C4 | −0.50 (17) | C9—C10—C11—C12 | −2.07 (17) |
C21—C2—C3—C4 | 179.16 (10) | C19—O5—C12—C13 | 87.73 (14) |
O6—C3—C4—C5 | −179.47 (10) | C19—O5—C12—C11 | −94.83 (13) |
C2—C3—C4—C5 | −0.27 (17) | O4—C11—C12—C13 | 177.68 (11) |
C9—O3—C5—C4 | −178.43 (9) | C10—C11—C12—C13 | −2.86 (18) |
C9—O3—C5—C6 | 0.85 (16) | O4—C11—C12—O5 | 0.25 (16) |
C3—C4—C5—O3 | −179.84 (9) | C10—C11—C12—O5 | 179.71 (10) |
C3—C4—C5—C6 | 0.88 (17) | O5—C12—C13—C8 | −177.12 (9) |
O3—C5—C6—C1 | −179.91 (9) | C11—C12—C13—C8 | 5.61 (17) |
C4—C5—C6—C1 | −0.68 (17) | O5—C12—C13—C14 | 8.53 (16) |
O3—C5—C6—C7 | 0.19 (16) | C11—C12—C13—C14 | −168.74 (10) |
C4—C5—C6—C7 | 179.42 (10) | C9—C8—C13—C12 | −3.47 (15) |
O1—C1—C6—C5 | 179.49 (10) | C7—C8—C13—C12 | 173.45 (10) |
C2—C1—C6—C5 | −0.15 (16) | C9—C8—C13—C14 | 170.59 (10) |
O1—C1—C6—C7 | −0.61 (17) | C7—C8—C13—C14 | −12.48 (17) |
C2—C1—C6—C7 | 179.75 (10) | C12—C13—C14—C15 | 98.57 (12) |
C5—C6—C7—O2 | −179.28 (11) | C8—C13—C14—C15 | −75.46 (13) |
C1—C6—C7—O2 | 0.83 (18) | C13—C14—C15—C16 | −103.65 (14) |
C5—C6—C7—C8 | −0.26 (16) | C14—C15—C16—C18 | −3.8 (2) |
C1—C6—C7—C8 | 179.84 (9) | C14—C15—C16—C17 | 176.53 (12) |
O2—C7—C8—C9 | 178.35 (11) | C1—C2—C21—C22 | 100.42 (13) |
C6—C7—C8—C9 | −0.64 (15) | C3—C2—C21—C22 | −79.23 (14) |
O2—C7—C8—C13 | 1.42 (18) | C2—C21—C22—C23 | −104.99 (14) |
C6—C7—C8—C13 | −177.57 (10) | C21—C22—C23—C25 | 2.4 (2) |
C5—O3—C9—C10 | 178.33 (9) | C21—C22—C23—C24 | −178.49 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O2 | 0.82 | 1.82 | 2.5558 (13) | 148 |
O4—H1O4···O5 | 0.85 (2) | 2.21 (2) | 2.6994 (14) | 117 (2) |
C14—H14A···O2 | 0.97 | 2.27 | 2.8283 (15) | 116 |
C14—H14B···O5 | 0.97 | 2.43 | 2.8573 (15) | 106 |
C18—H18A···O5 | 0.96 | 2.59 | 3.413 (2) | 144 |
C21—H21B···O1 | 0.97 | 2.40 | 2.8103 (15) | 105 |
C20—H20C···Cg1i | 0.96 | 2.84 | 3.6661 (16) | 144 |
C21—H21A···Cg1ii | 0.97 | 2.84 | 3.5627 (13) | 132 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C25H28O6 |
Mr | 424.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 7.8938 (1), 10.1976 (1), 13.7937 (2) |
α, β, γ (°) | 79.311 (1), 80.926 (1), 87.850 (1) |
V (Å3) | 1077.40 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.28 × 0.23 |
Data collection | |
Diffractometer | Bruker SMART APEX2 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.969, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16706, 5720, 4623 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.682 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.140, 1.06 |
No. of reflections | 5720 |
No. of parameters | 291 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.30, −0.21 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).
O1—C1 | 1.3489 (13) | O5—C19 | 1.4348 (18) |
O2—C7 | 1.2488 (13) | O6—C3 | 1.3602 (13) |
O3—C5 | 1.3663 (13) | O6—C20 | 1.4217 (16) |
O3—C9 | 1.3670 (12) | C15—C16 | 1.3274 (18) |
O4—C11 | 1.3566 (14) | C22—C23 | 1.3316 (18) |
O5—C12 | 1.3881 (13) | ||
C12—O5—C19 | 112.64 (10) | C3—O6—C20 | 118.14 (10) |
O1—C1—C2—C3 | −178.93 (10) | C19—O5—C12—C13 | 87.73 (14) |
C20—O6—C3—C4 | −0.80 (18) | O4—C11—C12—C13 | 177.68 (11) |
C21—C2—C3—C4 | 179.16 (10) | C11—C12—C13—C14 | −168.74 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O2 | 0.82 | 1.82 | 2.5558 (13) | 148 |
O4—H1O4···O5 | 0.85 (2) | 2.21 (2) | 2.6994 (14) | 117 (2) |
C14—H14A···O2 | 0.97 | 2.27 | 2.8283 (15) | 116 |
C14—H14B···O5 | 0.97 | 2.43 | 2.8573 (15) | 106 |
C18—H18A···O5 | 0.96 | 2.59 | 3.413 (2) | 144 |
C21—H21B···O1 | 0.97 | 2.40 | 2.8103 (15) | 105 |
C20—H20C···Cg1i | 0.96 | 2.84 | 3.6661 (16) | 144 |
C21—H21A···Cg1ii | 0.97 | 2.84 | 3.5627 (13) | 132 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z+1. |
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In our search for bioactive compounds from medicinal plants, we have investigated Cratoxylum formosum ssp. pruniflorum, which has been used for traditional medicine in Southeast Asia (Usher et al., 1984). The main components of this plant are xanthones and anthraquinones. We have previously reported the crystal structures of an anthraquinone and xanthones which were isolated from this plant, viz 3-O-(geranyl)anthraquinone (Boonnak, Chantrapromma, Fun, Anjum et al., 2005), xanthone V1 (Chantrapromma et al., 2005), prunifloxanthone A (Boonnak, Chantrapromma, Fun & Karalai, 2005) and macluraxanthone (Fun et al., 2006). The title compound, (I), β-mangostin, is another xanthone which is a secondary metabolite occurring in this plant. It has previously been isolated from Garcinia mangostana (Asai et al., 1995) and Cratoxylum cochinchinense (Nguyen & Harrison, 1999). Compound (I) has exhibited cytotoxicity against human leukaemia HL 60 cells (Matsumoto et al., 2003) and has antiproliferative effects against human colon cancer DLD-1 cells (Matsumoto et al., 2005).
The present single-crystal structure determination of (I) is part of our on-going search for bioactive compounds from Thai medicinal plants (Chantrapromma et al., 2003, 2004, 2005; Boonnak, Chantrapromma, Fun, Anjum et al., 2005; Boonnak, Chantrapromma, Fun & Karalai, 2005; Fun et al., 2005, 2006). The structure-activity relationship (SAR) of xanthone derivatives will be investigated further.
The molecular structure of (I) is shown in Fig. 1, and selected bond distances and angles are given in Table 1. The bond distances and angles show normal values (Allen et al., 1987) and are comparable with those in closely related structures (Boonnak, Chantrapromma, Fun & Chatchanok, 2005; Chantrapromma et al., 2005; Fun et al., 2006).
The xanthene ring system of (I) (C1–C13/O3) is almost planar, with all atoms lying within 0.088 (1) Å of the mean plane. The dihedral angle between the two benzene rings of xanthene is 3.97 (5)°. The two hydroxyl groups are each coplanar with the attached rings. The methoxy group attached at atom C3 is coplanar with the xanthene ring system, with a C20—O6—C3—C2 torsion angle of 179.94 (11)°, while the other methoxy group attached at atom C12 is twisted away, with a C19–O5–C12–C11 torsion angle of −94.83 (13)°, indicating a (-)-anticlinal conformation (Fig. 1).
The two 3-methylbut-2-enyl substituents are attached to the xanthene ring system at C2 and C13; the torsion angles C1–C2–C21–C22 and C12–C13–C14—C15 are 100.42 (13) and 98.57 (12)°, respectively, both indicating a (+)-anticlinal conformation (Fig. 1). The attachment of the two 3-methylbut-2-enyl substituents is different from that observed in prunifloxanthone A (Boonnak, Chantrapromma, Fun & Karalai, 2005), in which one of them is in a (+)-anticlinal conformation and the other in a (-)-anticlinal conformation. This is due to the attachment of a methoxy group at atom C12 in (I) compared with a hydroxyl group attached at the same position in prunifloxanthone A. We expect that these differences would affect the bioactivities of these compounds.
O1—H1O1···O2 and O4—H1O4···O5 intramolecular hydrogen bonds generate S(6) and S(5) ring motifs, respectively (Bernstein et al., 1995). There are also intramolecular C—H···O interactions present: C14—H14A···O2 generates an S(6) ring motif, C14—H14B···O5 generates an S(5) ring motif and C21—H21B···O1 generates an S(5) ring motif (Table 2). The crystal structure is stabilized by C—H···π interactions involving the C8–C13 benzene ring (centroid Cg1). The xanthene ring systems of inversion-related molecules are stacked in such a way that the centroids of the O3/C5–C9 ring at (x, y, z) and the C1–C6 benzene ring at (1 − x,-y,1 − z) are 3.5697 (6) Å apart, indicating significant π–π interaction (Fig. 2).