Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030801/wn6381sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030801/wn6381Isup2.hkl |
CCDC reference: 287749
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.063
- wR factor = 0.183
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.29 Ratio
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.98 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT480_ALERT_4_C Long H...A H-Bond Reported H23B .. CG1 .. 2.92 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C24 H26 O6
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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. cochinchinese (2 kg) were extracted successively with hexane. The hexane extract (17 g) was subjected to QCC over silica gel and eluted with a gradient of hexane-EtOAc to afford nine fractions (A1–A9). Fraction A2 was subjected to column chromatography using 20% EtOAc–hexane as eluent to give seve sub-fractions. Subfractions A2–2 (1.2 g) was crystallized from 20% EtOAc–hexane to yield compound (I) (0.5 g). Compound (I) was recrystallized from CHCl3/CH3OH (8:2 v/v) to give pale-yellow single crystals after several days (m.p. 431–432 K).
H atoms were placed in calculated positions, with an O—H distance of 0.82 Å and C—H distances in the range 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).
C24H26O6 | F(000) = 872 |
Mr = 410.45 | Dx = 1.287 Mg m−3 |
Monoclinic, P21/c | Melting point = 431–432 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.4622 (4) Å | Cell parameters from 4636 reflections |
b = 7.3284 (2) Å | θ = 1.6–27.0° |
c = 26.7829 (9) Å | µ = 0.09 mm−1 |
β = 109.709 (2)° | T = 273 K |
V = 2117.96 (12) Å3 | Block, pale yellow |
Z = 4 | 0.55 × 0.44 × 0.34 mm |
Bruker SMART APEX2 CCD area-detector diffractometer | 4636 independent reflections |
Radiation source: fine-focus sealed tube | 4048 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.0°, θmin = 1.6° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −9→9 |
Tmin = 0.953, Tmax = 0.969 | l = −34→34 |
35056 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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.183 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.063P)2 + 2.6144P] where P = (Fo2 + 2Fc2)/3 |
4636 reflections | (Δ/σ)max < 0.001 |
303 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C24H26O6 | V = 2117.96 (12) Å3 |
Mr = 410.45 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.4622 (4) Å | µ = 0.09 mm−1 |
b = 7.3284 (2) Å | T = 273 K |
c = 26.7829 (9) Å | 0.55 × 0.44 × 0.34 mm |
β = 109.709 (2)° |
Bruker SMART APEX2 CCD area-detector diffractometer | 4636 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 4048 reflections with I > 2σ(I) |
Tmin = 0.953, Tmax = 0.969 | Rint = 0.029 |
35056 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.183 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.19 e Å−3 |
4636 reflections | Δρmin = −0.28 e Å−3 |
303 parameters |
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 | 0.6190 (2) | −0.6835 (3) | −0.13501 (10) | 0.0576 (6) | |
H1A | 0.5544 | −0.6274 | −0.1393 | 0.066 (11)* | |
O2 | 0.40119 (18) | −0.6213 (3) | −0.12947 (9) | 0.0537 (5) | |
O3 | 0.39197 (16) | −1.1553 (2) | −0.08179 (8) | 0.0461 (5) | |
O4 | −0.04623 (18) | −1.0618 (3) | −0.15914 (9) | 0.0595 (6) | |
O5 | 0.15662 (16) | −1.3063 (2) | −0.09733 (7) | 0.0381 (4) | |
O6 | −0.01450 (16) | −0.7477 (3) | −0.09680 (8) | 0.0464 (5) | |
C1 | 0.4906 (2) | −1.0896 (3) | −0.09332 (9) | 0.0350 (5) | |
C2 | 0.5843 (2) | −1.2138 (4) | −0.08862 (11) | 0.0446 (6) | |
H2A | 0.5783 | −1.3332 | −0.0780 | 0.047 (8)* | |
C3 | 0.6883 (3) | −1.1566 (5) | −0.10003 (12) | 0.0543 (7) | |
H3A | 0.7514 | −1.2400 | −0.0971 | 0.059 (9)* | |
C4 | 0.7006 (3) | −0.9800 (5) | −0.11545 (13) | 0.0567 (8) | |
H4A | 0.7712 | −0.9451 | −0.1227 | 0.070 (10)* | |
C5 | 0.6070 (2) | −0.8560 (4) | −0.12005 (11) | 0.0437 (6) | |
C6 | 0.4988 (2) | −0.9086 (3) | −0.10913 (9) | 0.0342 (5) | |
C7 | 0.3982 (2) | −0.7818 (3) | −0.11517 (10) | 0.0358 (5) | |
C8 | 0.2896 (2) | −0.8545 (3) | −0.10443 (9) | 0.0322 (5) | |
C9 | 0.2842 (2) | −1.0490 (3) | −0.08752 (9) | 0.0310 (5) | |
C10 | 0.1699 (2) | −1.1477 (3) | −0.12578 (9) | 0.0328 (5) | |
C11 | 0.0565 (2) | −1.0232 (3) | −0.13146 (9) | 0.0357 (5) | |
C12 | 0.0888 (2) | −0.8519 (3) | −0.09569 (10) | 0.0341 (5) | |
C13 | 0.1888 (2) | −0.7545 (3) | −0.10999 (9) | 0.0327 (5) | |
H13A | 0.1809 | −0.6342 | −0.1217 | 0.042 (7)* | |
C14 | 0.1520 (2) | −0.9211 (3) | −0.03821 (10) | 0.0383 (5) | |
H14A | 0.1915 | −0.8197 | −0.0156 | 0.046 (8)* | |
H14B | 0.0898 | −0.9716 | −0.0250 | 0.056 (9)* | |
C15 | 0.2490 (2) | −1.0677 (3) | −0.03622 (9) | 0.0346 (5) | |
H15A | 0.3224 | −1.0525 | −0.0045 | 0.055 (9)* | |
C16 | 0.2001 (3) | −1.2680 (3) | −0.04028 (10) | 0.0412 (6) | |
C17 | 0.0911 (4) | −1.3012 (5) | −0.02121 (15) | 0.0668 (10) | |
H17A | 0.0678 | −1.4275 | −0.0260 | 0.081 (12)* | |
H17B | 0.0223 | −1.2269 | −0.0413 | 0.093 (15)* | |
H17C | 0.1143 | −1.2702 | 0.0157 | 0.092 (13)* | |
C18 | 0.3051 (4) | −1.4007 (4) | −0.01289 (12) | 0.0600 (8) | |
H18A | 0.2740 | −1.5234 | −0.0180 | 0.084 (12)* | |
H18B | 0.3372 | −1.3741 | 0.0244 | 0.076 (11)* | |
H18C | 0.3700 | −1.3880 | −0.0278 | 0.110 (17)* | |
C19 | 0.1767 (3) | −1.2086 (4) | −0.17904 (10) | 0.0437 (6) | |
H19A | 0.2428 | −1.2975 | −0.1730 | 0.064 (10)* | |
H19B | 0.0995 | −1.2681 | −0.1991 | 0.062 (10)* | |
C20 | 0.2000 (3) | −1.0542 (4) | −0.21134 (10) | 0.0446 (6) | |
H20A | 0.1449 | −0.9568 | −0.2175 | 0.061 (9)* | |
C21 | 0.2895 (3) | −1.0405 (5) | −0.23209 (10) | 0.0554 (8) | |
C22 | 0.3017 (5) | −0.8699 (7) | −0.26135 (15) | 0.0923 (16) | |
H22A | 0.2281 | −0.7975 | −0.2685 | 0.18 (3)* | |
H22B | 0.3128 | −0.9026 | −0.2942 | 0.101 (14)* | |
H22C | 0.3721 | −0.8010 | −0.2400 | 0.14 (2)* | |
C23 | 0.3839 (4) | −1.1860 (8) | −0.22836 (15) | 0.0895 (15) | |
H23A | 0.3759 | −1.2808 | −0.2050 | 0.13 (2)* | |
H23B | 0.4655 | −1.1342 | −0.2148 | 0.116 (18)* | |
H23C | 0.3707 | −1.2361 | −0.2629 | 0.15 (2)* | |
C24 | −0.0719 (3) | −0.6452 (5) | −0.14425 (15) | 0.0605 (9) | |
H24A | −0.1568 | −0.6214 | −0.1479 | 0.099 (14)* | |
H24B | −0.0686 | −0.7138 | −0.1743 | 0.099 (15)* | |
H24C | −0.0288 | −0.5317 | −0.1423 | 0.093 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0473 (12) | 0.0597 (13) | 0.0757 (14) | −0.0090 (10) | 0.0340 (11) | 0.0095 (11) |
O2 | 0.0518 (11) | 0.0338 (10) | 0.0863 (15) | −0.0036 (8) | 0.0374 (11) | 0.0110 (10) |
O3 | 0.0370 (9) | 0.0300 (9) | 0.0766 (13) | 0.0048 (7) | 0.0260 (9) | 0.0103 (8) |
O4 | 0.0355 (10) | 0.0641 (14) | 0.0708 (14) | −0.0091 (9) | 0.0074 (9) | −0.0163 (11) |
O5 | 0.0511 (10) | 0.0286 (8) | 0.0377 (9) | −0.0112 (7) | 0.0191 (8) | −0.0033 (7) |
O6 | 0.0383 (9) | 0.0463 (10) | 0.0609 (12) | 0.0096 (8) | 0.0248 (9) | 0.0047 (9) |
C1 | 0.0290 (11) | 0.0370 (12) | 0.0372 (12) | −0.0011 (9) | 0.0088 (9) | −0.0053 (10) |
C2 | 0.0382 (13) | 0.0458 (15) | 0.0459 (14) | 0.0070 (11) | 0.0091 (11) | −0.0017 (12) |
C3 | 0.0341 (13) | 0.069 (2) | 0.0597 (17) | 0.0117 (13) | 0.0152 (12) | −0.0053 (15) |
C4 | 0.0348 (13) | 0.078 (2) | 0.0637 (18) | −0.0018 (14) | 0.0253 (13) | −0.0060 (16) |
C5 | 0.0375 (13) | 0.0525 (16) | 0.0451 (14) | −0.0077 (11) | 0.0189 (11) | −0.0041 (12) |
C6 | 0.0295 (11) | 0.0386 (12) | 0.0354 (11) | −0.0025 (9) | 0.0120 (9) | −0.0031 (10) |
C7 | 0.0345 (12) | 0.0313 (11) | 0.0438 (13) | −0.0050 (9) | 0.0164 (10) | 0.0004 (10) |
C8 | 0.0324 (11) | 0.0266 (11) | 0.0395 (12) | −0.0015 (9) | 0.0147 (9) | 0.0011 (9) |
C9 | 0.0296 (11) | 0.0255 (10) | 0.0396 (12) | 0.0001 (8) | 0.0138 (9) | 0.0015 (9) |
C10 | 0.0375 (12) | 0.0287 (11) | 0.0353 (11) | −0.0046 (9) | 0.0164 (9) | −0.0016 (9) |
C11 | 0.0328 (11) | 0.0386 (12) | 0.0370 (12) | −0.0062 (10) | 0.0135 (10) | −0.0005 (10) |
C12 | 0.0310 (11) | 0.0326 (11) | 0.0417 (12) | 0.0014 (9) | 0.0159 (9) | 0.0008 (10) |
C13 | 0.0332 (11) | 0.0291 (11) | 0.0364 (11) | −0.0022 (9) | 0.0124 (9) | 0.0010 (9) |
C14 | 0.0491 (14) | 0.0345 (12) | 0.0363 (12) | −0.0015 (10) | 0.0211 (11) | −0.0026 (10) |
C15 | 0.0414 (12) | 0.0288 (11) | 0.0321 (11) | −0.0033 (9) | 0.0102 (10) | 0.0004 (9) |
C16 | 0.0597 (16) | 0.0313 (12) | 0.0361 (12) | −0.0069 (11) | 0.0206 (11) | −0.0002 (10) |
C17 | 0.099 (3) | 0.0504 (18) | 0.075 (2) | −0.0242 (19) | 0.060 (2) | −0.0057 (17) |
C18 | 0.091 (2) | 0.0316 (14) | 0.0495 (16) | −0.0005 (14) | 0.0130 (16) | 0.0071 (12) |
C19 | 0.0554 (16) | 0.0416 (14) | 0.0389 (13) | −0.0034 (12) | 0.0224 (12) | −0.0072 (11) |
C20 | 0.0501 (15) | 0.0512 (15) | 0.0341 (12) | −0.0006 (12) | 0.0164 (11) | −0.0020 (11) |
C21 | 0.0509 (16) | 0.086 (2) | 0.0312 (12) | −0.0106 (15) | 0.0164 (11) | −0.0034 (14) |
C22 | 0.106 (3) | 0.126 (4) | 0.0492 (19) | −0.049 (3) | 0.032 (2) | 0.006 (2) |
C23 | 0.067 (2) | 0.157 (5) | 0.054 (2) | 0.022 (3) | 0.0313 (18) | −0.011 (3) |
C24 | 0.0412 (15) | 0.0550 (18) | 0.083 (2) | 0.0129 (13) | 0.0178 (15) | 0.0206 (17) |
O1—C5 | 1.347 (3) | C13—H13A | 0.9300 |
O1—H1A | 0.8200 | C14—C15 | 1.534 (3) |
O2—C7 | 1.241 (3) | C14—H14A | 0.9693 |
O3—C1 | 1.356 (3) | C14—H14B | 0.9699 |
O3—C9 | 1.425 (3) | C15—C16 | 1.561 (3) |
O4—C11 | 1.195 (3) | C15—H15A | 0.9796 |
O5—C10 | 1.426 (3) | C16—C17 | 1.521 (4) |
O5—C16 | 1.466 (3) | C16—C18 | 1.529 (4) |
O6—C12 | 1.401 (3) | C17—H17A | 0.9600 |
O6—C24 | 1.431 (4) | C17—H17B | 0.9600 |
C1—C2 | 1.381 (3) | C17—H17C | 0.9600 |
C1—C6 | 1.405 (3) | C18—H18A | 0.9600 |
C2—C3 | 1.391 (4) | C18—H18B | 0.9600 |
C2—H2A | 0.9302 | C18—H18C | 0.9600 |
C3—C4 | 1.380 (5) | C19—C20 | 1.502 (4) |
C3—H3A | 0.9300 | C19—H19A | 0.9701 |
C4—C5 | 1.380 (4) | C19—H19B | 0.9706 |
C4—H4A | 0.9297 | C20—C21 | 1.325 (4) |
C5—C6 | 1.420 (3) | C20—H20A | 0.9300 |
C6—C7 | 1.446 (3) | C21—C23 | 1.499 (5) |
C7—C8 | 1.469 (3) | C21—C22 | 1.507 (5) |
C8—C13 | 1.334 (3) | C22—H22A | 0.9600 |
C8—C9 | 1.503 (3) | C22—H22B | 0.9600 |
C9—C10 | 1.544 (3) | C22—H22C | 0.9600 |
C9—C15 | 1.563 (3) | C23—H23A | 0.9600 |
C10—C19 | 1.522 (3) | C23—H23B | 0.9600 |
C10—C11 | 1.553 (3) | C23—H23C | 0.9600 |
C11—C12 | 1.546 (3) | C24—H24A | 0.9600 |
C12—C13 | 1.505 (3) | C24—H24B | 0.9600 |
C12—C14 | 1.549 (3) | C24—H24C | 0.9600 |
C5—O1—H1A | 109.5 | C12—C14—H14B | 109.5 |
C1—O3—C9 | 122.71 (18) | H14A—C14—H14B | 108.1 |
C10—O5—C16 | 109.93 (17) | C14—C15—C16 | 114.6 (2) |
C12—O6—C24 | 115.9 (2) | C14—C15—C9 | 107.85 (18) |
O3—C1—C2 | 115.3 (2) | C16—C15—C9 | 102.37 (18) |
O3—C1—C6 | 123.3 (2) | C14—C15—H15A | 110.5 |
C2—C1—C6 | 121.3 (2) | C16—C15—H15A | 110.5 |
C1—C2—C3 | 118.7 (3) | C9—C15—H15A | 110.6 |
C1—C2—H2A | 120.8 | O5—C16—C17 | 106.9 (2) |
C3—C2—H2A | 120.6 | O5—C16—C18 | 108.3 (2) |
C4—C3—C2 | 122.0 (3) | C17—C16—C18 | 109.9 (3) |
C4—C3—H3A | 119.1 | O5—C16—C15 | 103.93 (18) |
C2—C3—H3A | 118.9 | C17—C16—C15 | 116.3 (2) |
C5—C4—C3 | 119.3 (3) | C18—C16—C15 | 111.0 (2) |
C5—C4—H4A | 120.4 | C16—C17—H17A | 109.5 |
C3—C4—H4A | 120.3 | C16—C17—H17B | 109.5 |
O1—C5—C4 | 119.4 (2) | H17A—C17—H17B | 109.5 |
O1—C5—C6 | 120.0 (2) | C16—C17—H17C | 109.5 |
C4—C5—C6 | 120.6 (3) | H17A—C17—H17C | 109.5 |
C1—C6—C5 | 118.1 (2) | H17B—C17—H17C | 109.5 |
C1—C6—C7 | 120.5 (2) | C16—C18—H18A | 109.5 |
C5—C6—C7 | 121.4 (2) | C16—C18—H18B | 109.5 |
O2—C7—C6 | 122.7 (2) | H18A—C18—H18B | 109.5 |
O2—C7—C8 | 121.1 (2) | C16—C18—H18C | 109.5 |
C6—C7—C8 | 116.2 (2) | H18A—C18—H18C | 109.5 |
C13—C8—C7 | 122.6 (2) | H18B—C18—H18C | 109.5 |
C13—C8—C9 | 115.6 (2) | C20—C19—C10 | 113.2 (2) |
C7—C8—C9 | 121.8 (2) | C20—C19—H19A | 108.8 |
O3—C9—C8 | 115.36 (18) | C10—C19—H19A | 109.0 |
O3—C9—C10 | 109.02 (18) | C20—C19—H19B | 109.0 |
C8—C9—C10 | 110.89 (19) | C10—C19—H19B | 108.9 |
O3—C9—C15 | 109.18 (18) | H19A—C19—H19B | 107.8 |
C8—C9—C15 | 113.42 (18) | C21—C20—C19 | 127.7 (3) |
C10—C9—C15 | 97.45 (17) | C21—C20—H20A | 116.2 |
O5—C10—C19 | 108.08 (19) | C19—C20—H20A | 116.1 |
O5—C10—C9 | 104.29 (18) | C20—C21—C23 | 124.2 (3) |
C19—C10—C9 | 117.3 (2) | C20—C21—C22 | 120.1 (4) |
O5—C10—C11 | 107.16 (18) | C23—C21—C22 | 115.7 (3) |
C19—C10—C11 | 112.8 (2) | C21—C22—H22A | 109.5 |
C9—C10—C11 | 106.50 (18) | C21—C22—H22B | 109.5 |
O4—C11—C12 | 123.8 (2) | H22A—C22—H22B | 109.5 |
O4—C11—C10 | 122.6 (2) | C21—C22—H22C | 109.5 |
C12—C11—C10 | 113.51 (18) | H22A—C22—H22C | 109.5 |
O6—C12—C13 | 116.5 (2) | H22B—C22—H22C | 109.5 |
O6—C12—C11 | 113.90 (19) | C21—C23—H23A | 109.5 |
C13—C12—C11 | 105.72 (18) | C21—C23—H23B | 109.5 |
O6—C12—C14 | 107.96 (19) | H23A—C23—H23B | 109.5 |
C13—C12—C14 | 105.51 (19) | C21—C23—H23C | 109.5 |
C11—C12—C14 | 106.49 (19) | H23A—C23—H23C | 109.5 |
C8—C13—C12 | 114.6 (2) | H23B—C23—H23C | 109.5 |
C8—C13—H13A | 122.7 | O6—C24—H24A | 109.5 |
C12—C13—H13A | 122.7 | O6—C24—H24B | 109.5 |
C15—C14—C12 | 110.76 (19) | H24A—C24—H24B | 109.5 |
C15—C14—H14A | 109.5 | O6—C24—H24C | 109.5 |
C12—C14—H14A | 109.5 | H24A—C24—H24C | 109.5 |
C15—C14—H14B | 109.5 | H24B—C24—H24C | 109.5 |
C9—O3—C1—C2 | −176.3 (2) | C19—C10—C11—O4 | 49.2 (3) |
C9—O3—C1—C6 | 3.6 (4) | C9—C10—C11—O4 | 179.3 (2) |
O3—C1—C2—C3 | 179.7 (2) | O5—C10—C11—C12 | 107.2 (2) |
C6—C1—C2—C3 | −0.2 (4) | C19—C10—C11—C12 | −134.0 (2) |
C1—C2—C3—C4 | 0.5 (4) | C9—C10—C11—C12 | −4.0 (2) |
C2—C3—C4—C5 | −0.4 (5) | C24—O6—C12—C13 | 50.8 (3) |
C3—C4—C5—O1 | 179.9 (3) | C24—O6—C12—C11 | −72.8 (3) |
C3—C4—C5—C6 | −0.1 (4) | C24—O6—C12—C14 | 169.2 (2) |
O3—C1—C6—C5 | 179.9 (2) | O4—C11—C12—O6 | 2.4 (3) |
C2—C1—C6—C5 | −0.2 (4) | C10—C11—C12—O6 | −174.33 (19) |
O3—C1—C6—C7 | −1.5 (4) | O4—C11—C12—C13 | −126.8 (3) |
C2—C1—C6—C7 | 178.4 (2) | C10—C11—C12—C13 | 56.4 (2) |
O1—C5—C6—C1 | −179.6 (2) | O4—C11—C12—C14 | 121.3 (3) |
C4—C5—C6—C1 | 0.3 (4) | C10—C11—C12—C14 | −55.5 (2) |
O1—C5—C6—C7 | 1.8 (4) | C7—C8—C13—C12 | −178.5 (2) |
C4—C5—C6—C7 | −178.3 (3) | C9—C8—C13—C12 | 2.9 (3) |
C1—C6—C7—O2 | −179.4 (2) | O6—C12—C13—C8 | 175.0 (2) |
C5—C6—C7—O2 | −0.8 (4) | C11—C12—C13—C8 | −57.4 (3) |
C1—C6—C7—C8 | −0.6 (3) | C14—C12—C13—C8 | 55.2 (3) |
C5—C6—C7—C8 | 178.0 (2) | O6—C12—C14—C15 | 168.21 (19) |
O2—C7—C8—C13 | 0.9 (4) | C13—C12—C14—C15 | −66.5 (2) |
C6—C7—C8—C13 | −177.9 (2) | C11—C12—C14—C15 | 45.5 (2) |
O2—C7—C8—C9 | 179.5 (2) | C12—C14—C15—C16 | −93.7 (2) |
C6—C7—C8—C9 | 0.7 (3) | C12—C14—C15—C9 | 19.6 (3) |
C1—O3—C9—C8 | −3.2 (3) | O3—C9—C15—C14 | 167.66 (18) |
C1—O3—C9—C10 | 122.3 (2) | C8—C9—C15—C14 | 37.5 (3) |
C1—O3—C9—C15 | −132.3 (2) | C10—C9—C15—C14 | −79.2 (2) |
C13—C8—C9—O3 | 179.8 (2) | O3—C9—C15—C16 | −71.1 (2) |
C7—C8—C9—O3 | 1.1 (3) | C8—C9—C15—C16 | 158.7 (2) |
C13—C8—C9—C10 | 55.3 (3) | C10—C9—C15—C16 | 42.1 (2) |
C7—C8—C9—C10 | −123.4 (2) | C10—O5—C16—C17 | 120.7 (2) |
C13—C8—C9—C15 | −53.2 (3) | C10—O5—C16—C18 | −121.0 (2) |
C7—C8—C9—C15 | 128.1 (2) | C10—O5—C16—C15 | −2.9 (3) |
C16—O5—C10—C19 | 156.7 (2) | C14—C15—C16—O5 | 90.6 (2) |
C16—O5—C10—C9 | 31.1 (2) | C9—C15—C16—O5 | −25.8 (2) |
C16—O5—C10—C11 | −81.6 (2) | C14—C15—C16—C17 | −26.5 (3) |
O3—C9—C10—O5 | 68.3 (2) | C9—C15—C16—C17 | −143.0 (3) |
C8—C9—C10—O5 | −163.64 (17) | C14—C15—C16—C18 | −153.1 (2) |
C15—C9—C10—O5 | −45.0 (2) | C9—C15—C16—C18 | 90.4 (2) |
O3—C9—C10—C19 | −51.2 (3) | O5—C10—C19—C20 | −175.9 (2) |
C8—C9—C10—C19 | 76.9 (3) | C9—C10—C19—C20 | −58.5 (3) |
C15—C9—C10—C19 | −164.5 (2) | C11—C10—C19—C20 | 65.8 (3) |
O3—C9—C10—C11 | −178.57 (17) | C10—C19—C20—C21 | 125.5 (3) |
C8—C9—C10—C11 | −50.5 (2) | C19—C20—C21—C23 | 2.5 (5) |
C15—C9—C10—C11 | 68.1 (2) | C19—C20—C21—C22 | −177.1 (3) |
O5—C10—C11—O4 | −69.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2 | 0.82 | 1.86 | 2.591 (3) | 147 |
C13—H13A···O5i | 0.93 | 2.53 | 3.335 (3) | 145 |
C18—H18C···O3 | 0.96 | 2.30 | 2.978 (4) | 127 |
C24—H24B···O4 | 0.96 | 2.58 | 3.106 (4) | 115 |
C15—H15A···Cg1ii | 0.98 | 2.82 | 3.66 | 144 |
C23—H23B···Cg1 | 0.96 | 2.92 | 3.56 | 125 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y−2, −z. |
Experimental details
Crystal data | |
Chemical formula | C24H26O6 |
Mr | 410.45 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 11.4622 (4), 7.3284 (2), 26.7829 (9) |
β (°) | 109.709 (2) |
V (Å3) | 2117.96 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.55 × 0.44 × 0.34 |
Data collection | |
Diffractometer | Bruker SMART APEX2 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.953, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 35056, 4636, 4048 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.183, 1.09 |
No. of reflections | 4636 |
No. of parameters | 303 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.28 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).
O1—C5 | 1.347 (3) | O5—C16 | 1.466 (3) |
O2—C7 | 1.241 (3) | O6—C12 | 1.401 (3) |
O3—C1 | 1.356 (3) | O6—C24 | 1.431 (4) |
O3—C9 | 1.425 (3) | C8—C13 | 1.334 (3) |
O4—C11 | 1.195 (3) | C20—C21 | 1.325 (4) |
O5—C10 | 1.426 (3) | ||
C1—O3—C9 | 122.71 (18) | C12—C11—C10 | 113.51 (18) |
C10—O5—C16 | 109.93 (17) | O6—C12—C14 | 107.96 (19) |
C12—O6—C24 | 115.9 (2) | C16—C15—C9 | 102.37 (18) |
C19—C10—C11 | 112.8 (2) | C20—C19—C10 | 113.2 (2) |
C7—C8—C9—C15 | 128.1 (2) | O6—C12—C13—C8 | 175.0 (2) |
O3—C9—C10—O5 | 68.3 (2) | C9—C15—C16—C17 | −143.0 (3) |
C9—C10—C11—O4 | 179.3 (2) | C9—C15—C16—C18 | 90.4 (2) |
C24—O6—C12—C13 | 50.8 (3) | C9—C10—C19—C20 | −58.5 (3) |
C24—O6—C12—C14 | 169.2 (2) | C11—C10—C19—C20 | 65.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2 | 0.82 | 1.86 | 2.591 (3) | 147 |
C13—H13A···O5i | 0.93 | 2.53 | 3.335 (3) | 145 |
C18—H18C···O3 | 0.96 | 2.30 | 2.978 (4) | 127 |
C24—H24B···O4 | 0.96 | 2.58 | 3.106 (4) | 115 |
C15—H15A···Cg1ii | 0.98 | 2.82 | 3.66 | 144 |
C23—H23B···Cg1 | 0.96 | 2.92 | 3.56 | 125 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y−2, −z. |
The title compound, (I), is a caged-polyprenylated xanthone which has been isolated for the first time from Cratoxylum cochinchinese which was collected from Nhongkhai province in the northeastern part of Thailand. More importantly, (I) has never before been isolated from any natural product resources.
This plant is a medicinal plant belonging to the genus Cratoxylum (Bennett & Lee, 1989) and widely distributed, mainly in Southeast Asia. Some species of this genus have been used as traditional medicines (Usher, 1984). The bark, root and leaves of C. cochinchinese are used in folk medicines to treat fevers, coughs, diarrhea, itches, ulcers and abdominal complaints (Vo, 1997). As part of our research on bioactive compounds from medicinal plants (Chantrapromma et al., 2003, 2004; Chantrapromma, Boonnak et al., 2005; Chantrapromma, Fun et al., 2005; Boonnak et al., 2005; Fun et al., 2005), we have undertaken the X-ray crystal structure analysis of (I) in order to establish its molecular structure and relative stereochemistry.
Compound (I) is a chiral molecule, which crystallized in the centrosymmetric space group P21/c. This indicates that (I) was produced by non-enzymatic reactions during the chromatographic process (Chantrapromma, Boonnak et al., 2005; Chantrapromma, Fun et al., 2005).
The molecular structure of (I) is illustrated in Fig. 1, and selected bond distances and angles are given in Table 1. The bond lengths in (I) show normal values (Allen et al., 1987). In the xanthone skeleton (C1–C13/O2/O3), there are two cyclohexene rings, viz. C8–C13 and C8–C9/C12–C15. The former adopts a slightly twisted boat conformation and the latter has a twist–boat conformation, with puckering parameters Q = 0.778 (3), θ = 88.092)°, ϕ = 240.00 (18)° and Q = 0.765 (3), θ = 96.7 (2)°, ϕ = 49.62 (19)°, respectively (Cremer & Pople, 1975). The cyclohexane ring (C9–C12/C14–C15) is in a boat conformation; the tetrahydrofuran ring (O5/C10/C9/C15/C16) has an envelope conformation, with C9 as the most puckered atom [0.291 (2) Å] and Q = 0.463 (3) (Cremer & Pople, 1975). The hydroxyl group is coplanar with the attached benzene ring. The methoxy group is in a (+)-anti-periplanar conformation (Fig. 1), as evidenced by the torsion angle O6—C12—C13—C8 of 175.0 (2)°, The orientation of C11═O4 is defined by the C9—C10—C11—O4 torsion angle of 179.3 (2)°. The 3-methyl-2-butenyl (C19–C23) substituent group involves the C9—C10—C19—C20 torsion angle of −58.5 (3)°, indicating a (-)-synclinal conformation. The two methyl groups are axially and bisectionally attached to the tetrahydrofuran ring at atom C16.
The molecular structure is stabilized by intramolecular C—H···O interactions and O—H···O hydrogen bonds (Table 2). C—H···O intermolecular interactions link the molecules into molecular sheets parallel to the bc plane (Fig. 2). In addition, the molecular packing is stabilized by C—H···π interactions involving Cg1 where Cg1 is the centroid of the cyclohexene ring (C8–C13) (Table 2).