Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040328/wn6404sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040328/wn6404Isup2.hkl |
CCDC reference: 296728
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.055
- wR factor = 0.145
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Air-dried barks of C. formosum ssp. prunifolum (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 10 fractions (F1–F10). Fraction F3 was separated by column chromatography and eluted with 10% acetone-hexane to afford four fractions (3 A three-dimensional). Fraction 3 C was recrystallized from CHCl3—CH3OH (4:1 v/v) to yield, after several days, yellow needle-shaped crystals of (I), suitable for single-crystal X-ray diffraction (m.p. 456–457 K).
H atoms were placed in calculated positions, with O—H distances of 0.82 Å and C—H distances in the range 0.93–0.96 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).
C23H22O6 | F(000) = 832 |
Mr = 394.41 | Dx = 1.419 Mg m−3 |
Monoclinic, P21/c | Melting point = 456–457 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.0220 (8) Å | Cell parameters from 4452 reflections |
b = 16.1568 (8) Å | θ = 2.0–28.0° |
c = 8.4157 (4) Å | µ = 0.10 mm−1 |
β = 104.423 (4)° | T = 100 K |
V = 1846.49 (17) Å3 | Needle, yellow |
Z = 4 | 0.46 × 0.08 × 0.04 mm |
Bruker SMART APEX2 CCD area-detector diffractometer | 4452 independent reflections |
Radiation source: fine-focus sealed tube | 2789 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.076 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.0°, θmin = 2.0° |
ω scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −21→20 |
Tmin = 0.990, Tmax = 0.996 | l = −11→11 |
16825 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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0623P)2] where P = (Fo2 + 2Fc2)/3 |
4445 reflections | (Δ/σ)max < 0.001 |
266 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C23H22O6 | V = 1846.49 (17) Å3 |
Mr = 394.41 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.0220 (8) Å | µ = 0.10 mm−1 |
b = 16.1568 (8) Å | T = 100 K |
c = 8.4157 (4) Å | 0.46 × 0.08 × 0.04 mm |
β = 104.423 (4)° |
Bruker SMART APEX2 CCD area-detector diffractometer | 4452 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2789 reflections with I > 2σ(I) |
Tmin = 0.990, Tmax = 0.996 | Rint = 0.076 |
16825 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.34 e Å−3 |
4445 reflections | Δρmin = −0.25 e Å−3 |
266 parameters |
Experimental. The data were collected using the Oxford Cryosystem 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 | −0.16700 (11) | 1.09207 (9) | −0.56072 (17) | 0.0214 (4) | |
H1O1 | −0.1266 | 1.1289 | −0.5588 | 0.032* | |
O2 | 0.01745 (11) | 1.11209 (9) | −0.35932 (17) | 0.0200 (3) | |
H1O2 | 0.0744 | 1.1075 | −0.3044 | 0.030* | |
O3 | 0.09651 (10) | 0.99086 (9) | −0.13862 (16) | 0.0172 (3) | |
O4 | −0.06478 (10) | 0.78863 (9) | −0.06809 (18) | 0.0197 (3) | |
O5 | 0.08288 (10) | 0.73333 (8) | 0.13765 (17) | 0.0189 (3) | |
H1O5 | 0.0265 | 0.7357 | 0.0798 | 0.028* | |
O6 | 0.38313 (10) | 0.88140 (9) | 0.22057 (16) | 0.0176 (3) | |
C1 | −0.14871 (16) | 0.90275 (13) | −0.3253 (2) | 0.0175 (4) | |
H1A | −0.1869 | 0.8563 | −0.3193 | 0.021* | |
C2 | −0.18486 (16) | 0.96376 (13) | −0.4373 (3) | 0.0185 (5) | |
H2A | −0.2474 | 0.9586 | −0.5070 | 0.022* | |
C3 | −0.12778 (15) | 1.03380 (12) | −0.4469 (2) | 0.0166 (5) | |
C4 | −0.03367 (15) | 1.04212 (12) | −0.3443 (2) | 0.0158 (4) | |
C5 | 0.00232 (15) | 0.97925 (13) | −0.2330 (2) | 0.0155 (4) | |
C6 | −0.05423 (15) | 0.91002 (12) | −0.2197 (2) | 0.0151 (4) | |
C7 | −0.01437 (15) | 0.84925 (13) | −0.0945 (2) | 0.0167 (4) | |
C8 | 0.08641 (15) | 0.86223 (12) | −0.0011 (2) | 0.0151 (4) | |
C9 | 0.14119 (15) | 0.93157 (12) | −0.0278 (2) | 0.0151 (4) | |
C10 | 0.24054 (15) | 0.94440 (12) | 0.0521 (2) | 0.0148 (4) | |
C11 | 0.28389 (15) | 0.87927 (13) | 0.1574 (2) | 0.0152 (4) | |
C12 | 0.23198 (15) | 0.80908 (13) | 0.1906 (2) | 0.0161 (4) | |
C13 | 0.13354 (15) | 0.80157 (12) | 0.1120 (2) | 0.0150 (4) | |
C14 | 0.28653 (16) | 0.74394 (13) | 0.2955 (2) | 0.0180 (5) | |
H14A | 0.2564 | 0.6933 | 0.3030 | 0.022* | |
C15 | 0.37839 (16) | 0.75643 (13) | 0.3800 (3) | 0.0204 (5) | |
H15A | 0.4138 | 0.7135 | 0.4412 | 0.024* | |
C16 | 0.42543 (16) | 0.83917 (13) | 0.3775 (2) | 0.0181 (5) | |
C17 | 0.30106 (15) | 1.01906 (12) | 0.0149 (2) | 0.0157 (4) | |
C18 | 0.23859 (15) | 1.09555 (12) | −0.0437 (3) | 0.0177 (5) | |
H18A | 0.1918 | 1.1089 | 0.0134 | 0.021* | |
C19 | 0.24341 (16) | 1.14510 (14) | −0.1665 (3) | 0.0229 (5) | |
H19A | 0.2889 | 1.1347 | −0.2278 | 0.027* | |
H19B | 0.2013 | 1.1903 | −0.1916 | 0.027* | |
C20 | 0.37533 (16) | 1.05243 (13) | 0.1712 (3) | 0.0198 (5) | |
H20A | 0.4007 | 1.1049 | 0.1472 | 0.030* | |
H20B | 0.4286 | 1.0139 | 0.2050 | 0.030* | |
H20C | 0.3425 | 1.0591 | 0.2577 | 0.030* | |
C21 | 0.35830 (16) | 0.99066 (14) | −0.1090 (3) | 0.0199 (5) | |
H21A | 0.3127 | 0.9748 | −0.2096 | 0.030* | |
H21B | 0.3991 | 0.9443 | −0.0649 | 0.030* | |
H21D | 0.3988 | 1.0352 | −0.1299 | 0.030* | |
C22 | 0.53473 (16) | 0.83282 (14) | 0.3843 (3) | 0.0239 (5) | |
H22A | 0.5434 | 0.8010 | 0.2926 | 0.036* | |
H22B | 0.5684 | 0.8062 | 0.4846 | 0.036* | |
H22C | 0.5613 | 0.8873 | 0.3801 | 0.036* | |
C23 | 0.40736 (16) | 0.89315 (14) | 0.5157 (3) | 0.0213 (5) | |
H23A | 0.3378 | 0.8987 | 0.5040 | 0.032* | |
H23B | 0.4358 | 0.9468 | 0.5106 | 0.032* | |
H23C | 0.4371 | 0.8679 | 0.6194 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0180 (8) | 0.0223 (8) | 0.0214 (8) | −0.0017 (6) | 0.0002 (6) | 0.0065 (6) |
O2 | 0.0165 (8) | 0.0191 (8) | 0.0223 (8) | −0.0020 (6) | 0.0008 (6) | 0.0044 (6) |
O3 | 0.0152 (8) | 0.0173 (8) | 0.0170 (7) | −0.0011 (6) | 0.0001 (6) | 0.0036 (6) |
O4 | 0.0169 (8) | 0.0169 (8) | 0.0250 (8) | −0.0012 (6) | 0.0046 (6) | 0.0029 (6) |
O5 | 0.0166 (8) | 0.0173 (8) | 0.0215 (8) | −0.0020 (6) | 0.0026 (6) | 0.0047 (6) |
O6 | 0.0148 (8) | 0.0193 (8) | 0.0169 (7) | −0.0003 (6) | 0.0008 (6) | 0.0030 (6) |
C1 | 0.0181 (11) | 0.0162 (11) | 0.0186 (10) | −0.0015 (8) | 0.0053 (9) | −0.0021 (9) |
C2 | 0.0152 (11) | 0.0221 (11) | 0.0167 (10) | −0.0015 (9) | 0.0010 (8) | −0.0025 (9) |
C3 | 0.0178 (11) | 0.0165 (11) | 0.0152 (10) | 0.0031 (8) | 0.0034 (9) | 0.0005 (8) |
C4 | 0.0169 (11) | 0.0144 (10) | 0.0173 (10) | −0.0001 (8) | 0.0062 (8) | −0.0011 (9) |
C5 | 0.0126 (10) | 0.0204 (11) | 0.0131 (10) | 0.0022 (8) | 0.0026 (8) | −0.0014 (9) |
C6 | 0.0152 (11) | 0.0161 (11) | 0.0150 (10) | 0.0021 (8) | 0.0054 (8) | −0.0014 (8) |
C7 | 0.0173 (11) | 0.0166 (11) | 0.0178 (10) | 0.0013 (8) | 0.0072 (9) | −0.0018 (9) |
C8 | 0.0153 (11) | 0.0162 (10) | 0.0140 (10) | −0.0002 (8) | 0.0043 (8) | −0.0015 (9) |
C9 | 0.0186 (11) | 0.0135 (10) | 0.0133 (10) | 0.0039 (8) | 0.0041 (8) | 0.0004 (8) |
C10 | 0.0173 (11) | 0.0150 (10) | 0.0124 (10) | 0.0001 (8) | 0.0043 (8) | −0.0008 (8) |
C11 | 0.0134 (10) | 0.0199 (11) | 0.0118 (9) | 0.0007 (8) | 0.0019 (8) | −0.0034 (8) |
C12 | 0.0199 (11) | 0.0156 (10) | 0.0121 (10) | 0.0003 (8) | 0.0025 (8) | −0.0014 (8) |
C13 | 0.0186 (11) | 0.0131 (10) | 0.0141 (10) | 0.0009 (8) | 0.0055 (8) | −0.0027 (8) |
C14 | 0.0213 (12) | 0.0178 (11) | 0.0138 (10) | −0.0010 (9) | 0.0022 (9) | 0.0000 (9) |
C15 | 0.0223 (12) | 0.0194 (11) | 0.0180 (11) | 0.0035 (9) | 0.0024 (9) | 0.0044 (9) |
C16 | 0.0178 (11) | 0.0212 (11) | 0.0132 (10) | 0.0015 (9) | −0.0001 (8) | 0.0027 (9) |
C17 | 0.0140 (11) | 0.0167 (11) | 0.0156 (10) | −0.0005 (8) | 0.0019 (8) | −0.0003 (9) |
C18 | 0.0137 (11) | 0.0193 (11) | 0.0186 (10) | −0.0024 (8) | 0.0012 (8) | −0.0035 (9) |
C19 | 0.0191 (12) | 0.0208 (12) | 0.0274 (12) | 0.0002 (9) | 0.0032 (10) | 0.0013 (10) |
C20 | 0.0199 (11) | 0.0172 (11) | 0.0216 (11) | −0.0032 (9) | 0.0037 (9) | 0.0009 (9) |
C21 | 0.0185 (11) | 0.0203 (11) | 0.0212 (11) | −0.0009 (9) | 0.0055 (9) | 0.0002 (9) |
C22 | 0.0205 (12) | 0.0282 (13) | 0.0219 (11) | 0.0023 (10) | 0.0030 (9) | 0.0052 (10) |
C23 | 0.0197 (11) | 0.0251 (12) | 0.0174 (11) | −0.0016 (9) | 0.0012 (9) | −0.0007 (9) |
O1—C3 | 1.358 (2) | C12—C13 | 1.379 (3) |
O1—H1O1 | 0.8200 | C12—C14 | 1.462 (3) |
O2—C4 | 1.361 (2) | C14—C15 | 1.322 (3) |
O2—H1O2 | 0.8200 | C14—H14A | 0.9300 |
O3—C5 | 1.374 (2) | C15—C16 | 1.493 (3) |
O3—C9 | 1.375 (2) | C15—H15A | 0.9300 |
O4—C7 | 1.260 (2) | C16—C22 | 1.523 (3) |
O5—C13 | 1.358 (2) | C16—C23 | 1.525 (3) |
O5—H1O5 | 0.8200 | C17—C18 | 1.524 (3) |
O6—C11 | 1.361 (2) | C17—C21 | 1.536 (3) |
O6—C16 | 1.473 (2) | C17—C20 | 1.556 (3) |
C1—C2 | 1.371 (3) | C18—C19 | 1.322 (3) |
C1—C6 | 1.405 (3) | C18—H18A | 0.9300 |
C1—H1A | 0.9300 | C19—H19A | 0.9300 |
C2—C3 | 1.400 (3) | C19—H19B | 0.9300 |
C2—H2A | 0.9300 | C20—H20A | 0.9600 |
C3—C4 | 1.392 (3) | C20—H20B | 0.9600 |
C4—C5 | 1.389 (3) | C20—H20C | 0.9600 |
C5—C6 | 1.392 (3) | C21—H21A | 0.9600 |
C6—C7 | 1.447 (3) | C21—H21B | 0.9600 |
C7—C8 | 1.451 (3) | C21—H21D | 0.9600 |
C8—C9 | 1.408 (3) | C22—H22A | 0.9600 |
C8—C13 | 1.411 (3) | C22—H22B | 0.9600 |
C9—C10 | 1.403 (3) | C22—H22C | 0.9600 |
C10—C11 | 1.412 (3) | C23—H23A | 0.9600 |
C10—C17 | 1.551 (3) | C23—H23B | 0.9600 |
C11—C12 | 1.413 (3) | C23—H23C | 0.9600 |
C3—O1—H1O1 | 109.5 | C12—C14—H14A | 119.7 |
C4—O2—H1O2 | 109.5 | C14—C15—C16 | 120.2 (2) |
C5—O3—C9 | 120.47 (16) | C14—C15—H15A | 119.9 |
C13—O5—H1O5 | 109.5 | C16—C15—H15A | 119.9 |
C11—O6—C16 | 118.85 (15) | O6—C16—C15 | 110.28 (17) |
C2—C1—C6 | 120.28 (19) | O6—C16—C22 | 103.98 (16) |
C2—C1—H1A | 119.9 | C15—C16—C22 | 112.53 (18) |
C6—C1—H1A | 119.9 | O6—C16—C23 | 108.20 (16) |
C1—C2—C3 | 120.1 (2) | C15—C16—C23 | 110.09 (17) |
C1—C2—H2A | 119.9 | C22—C16—C23 | 111.52 (18) |
C3—C2—H2A | 119.9 | C18—C17—C21 | 112.21 (17) |
O1—C3—C4 | 121.69 (18) | C18—C17—C10 | 113.38 (16) |
O1—C3—C2 | 117.66 (18) | C21—C17—C10 | 108.02 (16) |
C4—C3—C2 | 120.64 (19) | C18—C17—C20 | 101.67 (16) |
O2—C4—C5 | 123.97 (19) | C21—C17—C20 | 108.92 (17) |
O2—C4—C3 | 117.54 (18) | C10—C17—C20 | 112.55 (16) |
C5—C4—C3 | 118.48 (18) | C19—C18—C17 | 127.4 (2) |
O3—C5—C4 | 115.18 (18) | C19—C18—H18A | 116.3 |
O3—C5—C6 | 123.25 (18) | C17—C18—H18A | 116.3 |
C4—C5—C6 | 121.57 (19) | C18—C19—H19A | 120.0 |
C5—C6—C1 | 118.87 (19) | C18—C19—H19B | 120.0 |
C5—C6—C7 | 118.65 (19) | H19A—C19—H19B | 120.0 |
C1—C6—C7 | 122.46 (18) | C17—C20—H20A | 109.5 |
O4—C7—C6 | 121.60 (19) | C17—C20—H20B | 109.5 |
O4—C7—C8 | 122.06 (19) | H20A—C20—H20B | 109.5 |
C6—C7—C8 | 116.34 (18) | C17—C20—H20C | 109.5 |
C9—C8—C13 | 118.55 (19) | H20A—C20—H20C | 109.5 |
C9—C8—C7 | 121.70 (19) | H20B—C20—H20C | 109.5 |
C13—C8—C7 | 119.63 (18) | C17—C21—H21A | 109.5 |
O3—C9—C10 | 116.90 (17) | C17—C21—H21B | 109.5 |
O3—C9—C8 | 119.22 (18) | H21A—C21—H21B | 109.5 |
C10—C9—C8 | 123.88 (19) | C17—C21—H21D | 109.5 |
C9—C10—C11 | 114.29 (18) | H21A—C21—H21D | 109.5 |
C9—C10—C17 | 123.09 (18) | H21B—C21—H21D | 109.5 |
C11—C10—C17 | 122.32 (18) | C16—C22—H22A | 109.5 |
O6—C11—C10 | 117.70 (18) | C16—C22—H22B | 109.5 |
O6—C11—C12 | 118.05 (18) | H22A—C22—H22B | 109.5 |
C10—C11—C12 | 124.05 (19) | C16—C22—H22C | 109.5 |
C13—C12—C11 | 118.62 (19) | H22A—C22—H22C | 109.5 |
C13—C12—C14 | 122.49 (19) | H22B—C22—H22C | 109.5 |
C11—C12—C14 | 118.66 (19) | C16—C23—H23A | 109.5 |
O5—C13—C12 | 119.71 (18) | C16—C23—H23B | 109.5 |
O5—C13—C8 | 119.73 (18) | H23A—C23—H23B | 109.5 |
C12—C13—C8 | 120.48 (18) | C16—C23—H23C | 109.5 |
C15—C14—C12 | 120.5 (2) | H23A—C23—H23C | 109.5 |
C15—C14—H14A | 119.7 | H23B—C23—H23C | 109.5 |
C6—C1—C2—C3 | −0.1 (3) | C16—O6—C11—C10 | 154.10 (17) |
C1—C2—C3—O1 | 179.59 (18) | C16—O6—C11—C12 | −30.8 (2) |
C1—C2—C3—C4 | 0.5 (3) | C9—C10—C11—O6 | 170.64 (16) |
O1—C3—C4—O2 | 1.5 (3) | C17—C10—C11—O6 | −3.3 (3) |
C2—C3—C4—O2 | −179.50 (17) | C9—C10—C11—C12 | −4.1 (3) |
O1—C3—C4—C5 | −178.76 (17) | C17—C10—C11—C12 | −178.06 (18) |
C2—C3—C4—C5 | 0.3 (3) | O6—C11—C12—C13 | −172.50 (17) |
C9—O3—C5—C4 | −177.90 (16) | C10—C11—C12—C13 | 2.2 (3) |
C9—O3—C5—C6 | 2.2 (3) | O6—C11—C12—C14 | 2.2 (3) |
O2—C4—C5—O3 | −1.7 (3) | C10—C11—C12—C14 | 176.94 (18) |
C3—C4—C5—O3 | 178.53 (17) | C11—C12—C13—O5 | 177.80 (17) |
O2—C4—C5—C6 | 178.18 (18) | C14—C12—C13—O5 | 3.3 (3) |
C3—C4—C5—C6 | −1.6 (3) | C11—C12—C13—C8 | 1.0 (3) |
O3—C5—C6—C1 | −178.06 (17) | C14—C12—C13—C8 | −173.49 (18) |
C4—C5—C6—C1 | 2.0 (3) | C9—C8—C13—O5 | −178.78 (17) |
O3—C5—C6—C7 | 3.5 (3) | C7—C8—C13—O5 | −2.8 (3) |
C4—C5—C6—C7 | −176.38 (18) | C9—C8—C13—C12 | −2.0 (3) |
C2—C1—C6—C5 | −1.2 (3) | C7—C8—C13—C12 | 173.98 (18) |
C2—C1—C6—C7 | 177.15 (18) | C13—C12—C14—C15 | −174.06 (19) |
C5—C6—C7—O4 | 174.51 (18) | C11—C12—C14—C15 | 11.5 (3) |
C1—C6—C7—O4 | −3.9 (3) | C12—C14—C15—C16 | 3.9 (3) |
C5—C6—C7—C8 | −5.3 (3) | C11—O6—C16—C15 | 43.4 (2) |
C1—C6—C7—C8 | 176.32 (18) | C11—O6—C16—C22 | 164.28 (17) |
O4—C7—C8—C9 | −177.92 (18) | C11—O6—C16—C23 | −77.0 (2) |
C6—C7—C8—C9 | 1.9 (3) | C14—C15—C16—O6 | −29.4 (3) |
O4—C7—C8—C13 | 6.3 (3) | C14—C15—C16—C22 | −145.0 (2) |
C6—C7—C8—C13 | −173.92 (17) | C14—C15—C16—C23 | 90.0 (2) |
C5—O3—C9—C10 | 173.95 (17) | C9—C10—C17—C18 | 28.8 (3) |
C5—O3—C9—C8 | −5.7 (3) | C11—C10—C17—C18 | −157.79 (18) |
C13—C8—C9—O3 | 179.47 (16) | C9—C10—C17—C21 | −96.2 (2) |
C7—C8—C9—O3 | 3.6 (3) | C11—C10—C17—C21 | 77.2 (2) |
C13—C8—C9—C10 | −0.2 (3) | C9—C10—C17—C20 | 143.51 (19) |
C7—C8—C9—C10 | −176.04 (18) | C11—C10—C17—C20 | −43.1 (2) |
O3—C9—C10—C11 | −176.61 (16) | C21—C17—C18—C19 | −13.3 (3) |
C8—C9—C10—C11 | 3.0 (3) | C10—C17—C18—C19 | −136.0 (2) |
O3—C9—C10—C17 | −2.7 (3) | C20—C17—C18—C19 | 102.9 (2) |
C8—C9—C10—C17 | 176.93 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O2 | 0.82 | 2.30 | 2.735 (2) | 114 |
O1—H1O1···O5i | 0.82 | 1.97 | 2.720 (2) | 153 |
O2—H1O2···O3 | 0.82 | 2.32 | 2.737 (2) | 112 |
O5—H1O5···O4 | 0.82 | 1.77 | 2.509 (2) | 150 |
C18—H18A···O4ii | 0.93 | 2.56 | 3.387 (3) | 149 |
C20—H20B···O6 | 0.96 | 2.25 | 2.792 (3) | 115 |
C23—H23A···O1ii | 0.96 | 2.56 | 3.492 (3) | 164 |
Symmetry codes: (i) −x, y+1/2, −z−1/2; (ii) −x, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C23H22O6 |
Mr | 394.41 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 14.0220 (8), 16.1568 (8), 8.4157 (4) |
β (°) | 104.423 (4) |
V (Å3) | 1846.49 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.46 × 0.08 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART APEX2 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.990, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16825, 4452, 2789 |
Rint | 0.076 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.145, 1.05 |
No. of reflections | 4445 |
No. of parameters | 266 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.25 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O2 | 0.82 | 2.2984 | 2.735 (2) | 114 |
O1—H1O1···O5i | 0.82 | 1.9661 | 2.720 (2) | 153 |
O2—H1O2···O3 | 0.82 | 2.3192 | 2.737 (2) | 112 |
O5—H1O5···O4 | 0.82 | 1.7678 | 2.509 (2) | 150 |
C18—H18A···O4ii | 0.93 | 2.5561 | 3.387 (3) | 149 |
C20—H20B···O6 | 0.96 | 2.2468 | 2.792 (3) | 115 |
C23—H23A···O1ii | 0.96 | 2.5604 | 3.492 (3) | 164 |
Symmetry codes: (i) −x, y+1/2, −z−1/2; (ii) −x, −y+2, −z. |
We have previously reported the crystal structures of a xanthone and a modified rotenoid containing the chromene ring, viz 5,9,10-trihydroxy-2,2- dimethyl-12-(3-methylbut-2-enyl)-2H,6H-pyrano[3,2-b]xanthen-6-one methanol solvate (Chantrapromma, Boonnak et al., 2005) and 7a-O-methyldeguelol (Chantrapromma, Fun et al., 2005). The title compound, (I), is another xanthone containing a chromene ring; since it also crystallized in the centrosymmetric space group P21/c, this indicates that (I) had been produced by non-enzymatic cyclization of a side chain (Chantrapromma, Boonnak et al., 2005; Chantrapromma, Fun et al., 2005).
Compound (I), macluraxanthone, was isolated from the bark of Cratoxylum formosum ssp. prunifolum, a shrub that was collected from Nhongkhai province in the northeastern part of Thailand. In our continuing search for bioactive compounds obtained from Thai medicinal plants (Chantrapromma et al., 2004; Chantrapromma, Boonnak et al., 2005; Chantrapromma, Fun et al., 2005; Boonnak et al., 2005; Fun et al., 2005; Boonsri et al., 2005), we have investigated C. formosum ssp. pruniflorum. Compound (I) has been reported previously (Monache et al., 1981; Menache et al., 1983; Goh et al., 1992), but its X-ray crystal structure has not yet been reported.
The molecular structure of (I) is shown in Fig. 1. The bond distances and angles show normal values (Allen et al., 1987) and are comparable to those in related structures (Chantrapromma & Boonnak et al., 2005; Ravikumar et al., 1987; Doriguetto et al., 2001).
The xanthene ring system (C1–C13/O3) is almost planar, with all atoms lying within 0.066 (2) Å of the mean plane. The three individual rings of xanthene are each essentially planar, the largest deviations from the ring planes being 0.010 (2), 0.033 (2) and 0.022 (2) Å for atoms C5, C6 and C9, C10 of rings A, B, and C, respectively. The dihedral angle between rings A and B is 2.60 (9)°, rings B and C form a dihedral angle of 5.73 (9)°, and the dihedral angle bewteen rings C and A is 7.77 (9)°. The chromene ring, D, adopts a screw-boat conformation (Cremer & Pople, 1975), with puckering parameters Q = 0.348 (2) Å, θ = 64.0 (3)° and ϕ2 = 326.7 (4)°. The three hydroxyl groups are each coplanar with the attached rings. Atom C17 of the 1,1-dimethyl-2-propenyl substituent is coplanar with ring C; the torsion angle C8—C9—C10—C17 is 176.93 (18)°.
In the crystal structure, there are intermolecular O1—H1O1···O5(−x, 1/2 + y, −1/2 − z), C17—H17A···O5(−x, 2 − y, −z) and C18—H18A···O4 (−x, 2 − y, −z) hydrogen bonds (Table 1). The molecules are linked by O—H···O intermolecular hydrogen bonds to form infinite chains along the b axis (Fig. 2). These chains form layers approximately parallel to the ab plane and are interconnected by the C—H···O interactions.