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The X-ray crystal structure of the title compound, C
25H
28O
8, has been determined. In the structure, both the terminal five-membered rings (
A and
F) are planar. The fused five-membered rings
C and
E are in envelope conformations, and ring
B is in a slightly distorted half-chair conformation. The six-membered ring
D is in a slightly distorted sofa conformation. The structure is stabilized by O—H
O hydrogen bonds and C—H
O inter- and intramolecular interactions.
Supporting information
CCDC reference: 159722
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.033
- wR factor = 0.092
- Data-to-parameter ratio = 8.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 69.93
From the CIF: _reflns_number_total 2417
Count of symmetry unique reflns 2488
Completeness (_total/calc) 97.15%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
The title compound was isolated from Cneorum tricoccin L., a shrub native
to coastal areas of the western Mediterranean with hairless leaves, yellow
blossoms and red fruits (Herz et al., 1983). It was crystallized from
ethanol/acetone.
The data set contains no Friedel pairs.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP (Frenz, 1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1998); software used to prepare material for publication: SHELXL97 and PARST97 (Nardelli, 1995).
Crystal data top
C25H28O8 | Dx = 1.325 Mg m−3 |
Mr = 456.47 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 7.224 (2) Å | θ = 20–30° |
b = 15.521 (2) Å | µ = 0.82 mm−1 |
c = 20.404 (1) Å | T = 293 K |
V = 2287.8 (7) Å3 | Needle, colourless |
Z = 4 | 0.25 × 0.25 × 0.20 mm |
F(000) = 968 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 69.9°, θmin = 3.6° |
Graphite monochromator | h = 0→8 |
ω/2θ scans | k = 0→18 |
2417 measured reflections | l = 0→24 |
2417 independent reflections | 3 standard reflections every 120 min |
2171 reflections with I > 2σ(I) | intensity decay: <1% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0539P)2 + 0.3026P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.092 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.19 e Å−3 |
2417 reflections | Δρmin = −0.17 e Å−3 |
303 parameters | Extinction correction: SHELXL07, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0078 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.2 (2) |
Crystal data top
C25H28O8 | V = 2287.8 (7) Å3 |
Mr = 456.47 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.224 (2) Å | µ = 0.82 mm−1 |
b = 15.521 (2) Å | T = 293 K |
c = 20.404 (1) Å | 0.25 × 0.25 × 0.20 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
2417 measured reflections | 3 standard reflections every 120 min |
2417 independent reflections | intensity decay: <1% |
2171 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.092 | Δρmax = 0.19 e Å−3 |
S = 1.04 | Δρmin = −0.17 e Å−3 |
2417 reflections | Absolute structure: Flack (1983) |
303 parameters | Absolute structure parameter: 0.2 (2) |
0 restraints | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | −0.0011 (4) | 0.44829 (18) | 0.91298 (12) | 0.0514 (6) | |
H1 | −0.0884 | 0.4147 | 0.9347 | 0.062* | |
C2 | 0.0661 (5) | 0.43112 (18) | 0.85488 (13) | 0.0582 (7) | |
H2 | 0.0317 | 0.3849 | 0.8286 | 0.070* | |
C3 | 0.2029 (5) | 0.49599 (17) | 0.83820 (12) | 0.0576 (7) | |
C4 | 0.3046 (4) | 0.58439 (16) | 1.03575 (12) | 0.0522 (6) | |
C5 | 0.1881 (4) | 0.51129 (15) | 1.00390 (10) | 0.0421 (5) | |
H5 | 0.0954 | 0.4942 | 1.0364 | 0.051* | |
C6 | 0.3230 (4) | 0.43608 (14) | 0.99777 (11) | 0.0427 (5) | |
H6A | 0.2593 | 0.3813 | 1.0019 | 0.051* | |
H6B | 0.3879 | 0.4377 | 0.9562 | 0.051* | |
C7 | 0.4547 (4) | 0.45026 (14) | 1.05433 (11) | 0.0408 (5) | |
C8 | 0.6596 (3) | 0.34735 (13) | 1.10470 (10) | 0.0355 (5) | |
C9 | 0.5305 (3) | 0.39130 (15) | 1.15372 (10) | 0.0396 (5) | |
H9 | 0.5905 | 0.4432 | 1.1710 | 0.047* | |
C10 | 0.0822 (4) | 0.52963 (15) | 0.93978 (11) | 0.0445 (5) | |
C11 | 0.4825 (4) | 0.33158 (17) | 1.20975 (11) | 0.0469 (6) | |
H11A | 0.4279 | 0.2790 | 1.1928 | 0.056* | |
H11B | 0.3931 | 0.3590 | 1.2384 | 0.056* | |
C12 | 0.6596 (4) | 0.31011 (19) | 1.24852 (11) | 0.0518 (6) | |
H12A | 0.6800 | 0.3555 | 1.2804 | 0.062* | |
H12B | 0.6384 | 0.2572 | 1.2727 | 0.062* | |
C13 | 0.8365 (3) | 0.29927 (14) | 1.20829 (10) | 0.0372 (5) | |
C14 | 0.8410 (3) | 0.32540 (13) | 1.13677 (10) | 0.0357 (5) | |
C15 | 0.9635 (4) | 0.26286 (16) | 1.10388 (11) | 0.0441 (5) | |
O16 | 1.0349 (3) | 0.20671 (11) | 1.14794 (8) | 0.0543 (5) | |
C17 | 0.9415 (4) | 0.21545 (14) | 1.21156 (10) | 0.0417 (5) | |
H17 | 0.8513 | 0.1686 | 1.2155 | 0.050* | |
C18 | 0.9432 (4) | 0.37711 (14) | 1.18752 (10) | 0.0406 (5) | |
H18A | 1.0772 | 0.3734 | 1.1879 | 0.049* | |
H18B | 0.8935 | 0.4331 | 1.1991 | 0.049* | |
C19 | −0.0644 (5) | 0.6001 (2) | 0.94640 (15) | 0.0669 (8) | |
H19A | −0.0058 | 0.6533 | 0.9584 | 0.100* | |
H19B | −0.1519 | 0.5841 | 0.9796 | 0.100* | |
H19C | −0.1274 | 0.6072 | 0.9053 | 0.100* | |
C20 | 1.0822 (3) | 0.20472 (14) | 1.26463 (11) | 0.0414 (5) | |
C21 | 1.1910 (5) | 0.13015 (17) | 1.27584 (14) | 0.0588 (7) | |
H21 | 1.1909 | 0.0798 | 1.2511 | 0.071* | |
C22 | 1.1283 (4) | 0.26077 (17) | 1.31191 (12) | 0.0503 (6) | |
H22 | 1.0786 | 0.3158 | 1.3163 | 0.060* | |
C23 | 1.2935 (5) | 0.14616 (19) | 1.32873 (16) | 0.0681 (8) | |
H23 | 1.3781 | 0.1079 | 1.3469 | 0.082* | |
O24 | 1.2571 (3) | 0.22641 (13) | 1.35249 (9) | 0.0662 (6) | |
O25 | 1.0044 (3) | 0.25932 (14) | 1.04679 (8) | 0.0633 (6) | |
O26 | 0.5807 (3) | 0.26671 (11) | 1.08654 (7) | 0.0492 (4) | |
H26 | 0.5599 | 0.2665 | 1.0470 | 0.074* | |
O27 | 0.3774 (2) | 0.41558 (11) | 1.11359 (8) | 0.0493 (4) | |
C28 | 0.3810 (6) | 0.65439 (18) | 0.99111 (18) | 0.0801 (11) | |
H28A | 0.4712 | 0.6877 | 1.0145 | 0.120* | |
H28B | 0.2818 | 0.6912 | 0.9771 | 0.120* | |
H28C | 0.4380 | 0.6284 | 0.9535 | 0.120* | |
C29 | 0.2061 (6) | 0.6227 (3) | 1.09453 (17) | 0.0929 (13) | |
H29A | 0.1845 | 0.5784 | 1.1265 | 0.139* | |
H29B | 0.0900 | 0.6468 | 1.0809 | 0.139* | |
H29C | 0.2816 | 0.6671 | 1.1135 | 0.139* | |
C30 | 0.6516 (3) | 0.41203 (15) | 1.04874 (11) | 0.0422 (5) | |
H30A | 0.6693 | 0.3838 | 1.0068 | 0.051* | |
H30B | 0.7450 | 0.4564 | 1.0540 | 0.051* | |
O31 | 0.4710 (3) | 0.54090 (10) | 1.05931 (8) | 0.0506 (4) | |
O32 | 0.2099 (3) | 0.55420 (10) | 0.88795 (8) | 0.0519 (5) | |
O33 | 0.3017 (4) | 0.50316 (15) | 0.79069 (10) | 0.0880 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0454 (14) | 0.0577 (15) | 0.0513 (13) | −0.0012 (12) | −0.0097 (12) | 0.0012 (11) |
C2 | 0.0699 (18) | 0.0536 (14) | 0.0509 (14) | 0.0031 (15) | −0.0113 (15) | −0.0073 (12) |
C3 | 0.085 (2) | 0.0476 (13) | 0.0404 (12) | 0.0124 (15) | 0.0016 (14) | 0.0050 (10) |
C4 | 0.0616 (15) | 0.0431 (12) | 0.0518 (13) | 0.0092 (13) | −0.0173 (13) | −0.0084 (11) |
C5 | 0.0481 (13) | 0.0423 (12) | 0.0359 (10) | 0.0025 (11) | −0.0040 (11) | 0.0025 (9) |
C6 | 0.0530 (14) | 0.0347 (10) | 0.0405 (11) | 0.0000 (11) | −0.0110 (11) | 0.0019 (9) |
C7 | 0.0464 (13) | 0.0373 (11) | 0.0387 (11) | −0.0018 (10) | −0.0062 (11) | 0.0041 (9) |
C8 | 0.0409 (12) | 0.0371 (10) | 0.0285 (9) | −0.0033 (10) | −0.0042 (9) | −0.0004 (8) |
C9 | 0.0400 (12) | 0.0466 (12) | 0.0321 (10) | 0.0032 (10) | −0.0028 (10) | 0.0032 (9) |
C10 | 0.0500 (14) | 0.0450 (12) | 0.0386 (11) | 0.0064 (12) | −0.0053 (11) | 0.0028 (9) |
C11 | 0.0436 (13) | 0.0609 (15) | 0.0361 (11) | 0.0058 (12) | 0.0078 (10) | 0.0085 (11) |
C12 | 0.0503 (14) | 0.0744 (16) | 0.0306 (10) | 0.0073 (14) | 0.0034 (11) | 0.0076 (11) |
C13 | 0.0433 (12) | 0.0420 (11) | 0.0263 (9) | 0.0028 (10) | −0.0035 (9) | 0.0001 (8) |
C14 | 0.0420 (12) | 0.0392 (10) | 0.0260 (9) | 0.0022 (10) | 0.0003 (9) | −0.0009 (8) |
C15 | 0.0516 (14) | 0.0482 (12) | 0.0325 (10) | 0.0086 (12) | −0.0049 (11) | −0.0062 (10) |
O16 | 0.0690 (12) | 0.0543 (10) | 0.0397 (8) | 0.0241 (10) | −0.0051 (9) | −0.0084 (7) |
C17 | 0.0511 (13) | 0.0381 (11) | 0.0359 (11) | 0.0004 (11) | −0.0052 (11) | 0.0008 (9) |
C18 | 0.0433 (12) | 0.0394 (11) | 0.0389 (11) | 0.0012 (11) | −0.0057 (10) | −0.0048 (9) |
C19 | 0.0720 (19) | 0.0659 (17) | 0.0626 (16) | 0.0297 (17) | −0.0152 (16) | −0.0024 (14) |
C20 | 0.0440 (12) | 0.0425 (11) | 0.0378 (11) | −0.0012 (11) | −0.0032 (11) | 0.0081 (9) |
C21 | 0.0704 (18) | 0.0452 (13) | 0.0610 (16) | 0.0073 (14) | −0.0120 (16) | 0.0076 (11) |
C22 | 0.0542 (15) | 0.0527 (13) | 0.0441 (12) | 0.0013 (13) | −0.0103 (12) | 0.0048 (10) |
C23 | 0.070 (2) | 0.0601 (16) | 0.0739 (19) | 0.0127 (17) | −0.0188 (18) | 0.0142 (15) |
O24 | 0.0727 (13) | 0.0695 (12) | 0.0564 (10) | 0.0022 (11) | −0.0275 (11) | 0.0063 (10) |
O25 | 0.0757 (13) | 0.0805 (13) | 0.0338 (8) | 0.0208 (12) | 0.0058 (9) | −0.0108 (8) |
O26 | 0.0654 (11) | 0.0465 (9) | 0.0357 (8) | −0.0133 (9) | −0.0100 (8) | −0.0013 (7) |
O27 | 0.0399 (8) | 0.0663 (10) | 0.0418 (8) | 0.0062 (9) | −0.0021 (7) | 0.0143 (8) |
C28 | 0.097 (3) | 0.0426 (14) | 0.101 (2) | −0.0143 (17) | −0.037 (2) | 0.0130 (15) |
C29 | 0.087 (2) | 0.107 (3) | 0.086 (2) | 0.030 (2) | −0.024 (2) | −0.054 (2) |
C30 | 0.0431 (12) | 0.0481 (12) | 0.0353 (10) | −0.0009 (11) | −0.0013 (10) | 0.0075 (10) |
O31 | 0.0581 (11) | 0.0396 (8) | 0.0541 (9) | −0.0007 (8) | −0.0170 (9) | −0.0033 (7) |
O32 | 0.0704 (12) | 0.0416 (8) | 0.0438 (8) | 0.0012 (9) | 0.0013 (9) | 0.0082 (7) |
O33 | 0.131 (2) | 0.0753 (13) | 0.0579 (12) | 0.0085 (16) | 0.0324 (15) | 0.0096 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.309 (4) | C12—H12B | 0.970 |
C1—C10 | 1.501 (4) | C13—C18 | 1.494 (3) |
C1—H1 | 0.930 | C13—C17 | 1.507 (3) |
C2—C3 | 1.452 (4) | C13—C14 | 1.515 (3) |
C2—H2 | 0.930 | C14—C15 | 1.475 (3) |
C3—O33 | 1.209 (3) | C14—C18 | 1.504 (3) |
C3—O32 | 1.360 (3) | C15—O25 | 1.203 (3) |
C4—O31 | 1.460 (3) | C15—O16 | 1.354 (3) |
C4—C29 | 1.516 (4) | O16—C17 | 1.469 (3) |
C4—C28 | 1.521 (4) | C17—C20 | 1.494 (3) |
C4—C5 | 1.555 (3) | C17—H17 | 0.980 |
C5—C6 | 1.526 (3) | C18—H18A | 0.970 |
C5—C10 | 1.542 (3) | C18—H18B | 0.970 |
C5—H5 | 0.980 | C19—H19A | 0.960 |
C6—C7 | 1.512 (3) | C19—H19B | 0.960 |
C6—H6A | 0.970 | C19—H19C | 0.960 |
C6—H6B | 0.970 | C20—C22 | 1.341 (3) |
C7—O31 | 1.415 (3) | C20—C21 | 1.418 (3) |
C7—O27 | 1.437 (3) | C21—C23 | 1.332 (4) |
C7—C30 | 1.546 (4) | C21—H21 | 0.930 |
C8—O26 | 1.424 (3) | C22—O24 | 1.355 (3) |
C8—C14 | 1.504 (3) | C22—H22 | 0.930 |
C8—C30 | 1.521 (3) | C23—O24 | 1.362 (4) |
C8—C9 | 1.528 (3) | C23—H23 | 0.930 |
C9—O27 | 1.427 (3) | O26—H26 | 0.820 |
C9—C11 | 1.512 (3) | C28—H28A | 0.960 |
C9—H9 | 0.980 | C28—H28B | 0.960 |
C10—O32 | 1.455 (3) | C28—H28C | 0.960 |
C10—C19 | 1.528 (4) | C29—H29A | 0.960 |
C11—C12 | 1.541 (4) | C29—H29B | 0.960 |
C11—H11A | 0.970 | C29—H29C | 0.960 |
C11—H11B | 0.970 | C30—H30A | 0.970 |
C12—C13 | 1.528 (3) | C30—H30B | 0.970 |
C12—H12A | 0.970 | | |
| | | |
C2—C1—C10 | 110.6 (3) | C18—C13—C12 | 119.6 (2) |
C2—C1—H1 | 124.7 | C17—C13—C12 | 119.5 (2) |
C10—C1—H1 | 124.7 | C14—C13—C12 | 120.4 (2) |
C1—C2—C3 | 108.9 (2) | C15—C14—C18 | 111.7 (2) |
C1—C2—H2 | 125.6 | C15—C14—C8 | 118.29 (18) |
C3—C2—H2 | 125.6 | C18—C14—C8 | 127.33 (19) |
O33—C3—O32 | 121.0 (3) | C15—C14—C13 | 105.96 (18) |
O33—C3—C2 | 130.8 (3) | C18—C14—C13 | 59.34 (14) |
O32—C3—C2 | 108.1 (2) | C8—C14—C13 | 117.5 (2) |
O31—C4—C29 | 107.9 (2) | O25—C15—O16 | 121.3 (2) |
O31—C4—C28 | 103.2 (3) | O25—C15—C14 | 128.2 (2) |
C29—C4—C28 | 111.3 (3) | O16—C15—C14 | 110.48 (18) |
O31—C4—C5 | 104.23 (18) | C15—O16—C17 | 110.62 (17) |
C29—C4—C5 | 111.3 (3) | O16—C17—C20 | 108.5 (2) |
C28—C4—C5 | 117.9 (2) | O16—C17—C13 | 105.76 (17) |
C6—C5—C10 | 112.87 (18) | C20—C17—C13 | 118.06 (19) |
C6—C5—C4 | 104.30 (19) | O16—C17—H17 | 108.0 |
C10—C5—C4 | 119.2 (2) | C20—C17—H17 | 108.0 |
C6—C5—H5 | 106.6 | C13—C17—H17 | 108.0 |
C10—C5—H5 | 106.6 | C13—C18—C14 | 60.70 (14) |
C4—C5—H5 | 106.6 | C13—C18—H18A | 117.7 |
C7—C6—C5 | 103.17 (18) | C14—C18—H18A | 117.7 |
C7—C6—H6A | 111.1 | C13—C18—H18B | 117.7 |
C5—C6—H6A | 111.1 | C14—C18—H18B | 117.7 |
C7—C6—H6B | 111.1 | H18A—C18—H18B | 114.8 |
C5—C6—H6B | 111.1 | C10—C19—H19A | 109.5 |
H6A—C6—H6B | 109.1 | C10—C19—H19B | 109.5 |
O31—C7—O27 | 110.14 (19) | H19A—C19—H19B | 109.5 |
O31—C7—C6 | 104.60 (18) | C10—C19—H19C | 109.5 |
O27—C7—C6 | 110.07 (19) | H19A—C19—H19C | 109.5 |
O31—C7—C30 | 108.1 (2) | H19B—C19—H19C | 109.5 |
O27—C7—C30 | 106.03 (17) | C22—C20—C21 | 106.0 (2) |
C6—C7—C30 | 117.8 (2) | C22—C20—C17 | 128.2 (2) |
O26—C8—C14 | 105.23 (17) | C21—C20—C17 | 125.8 (2) |
O26—C8—C30 | 111.68 (17) | C23—C21—C20 | 106.7 (3) |
C14—C8—C30 | 120.60 (19) | C23—C21—H21 | 126.7 |
O26—C8—C9 | 108.57 (19) | C20—C21—H21 | 126.7 |
C14—C8—C9 | 110.38 (16) | C20—C22—O24 | 110.8 (2) |
C30—C8—C9 | 100.00 (17) | C20—C22—H22 | 124.6 |
O27—C9—C11 | 114.72 (19) | O24—C22—H22 | 124.6 |
O27—C9—C8 | 102.44 (16) | C21—C23—O24 | 110.6 (3) |
C11—C9—C8 | 111.17 (19) | C21—C23—H23 | 124.7 |
O27—C9—H9 | 109.4 | O24—C23—H23 | 124.7 |
C11—C9—H9 | 109.4 | C22—O24—C23 | 106.0 (2) |
C8—C9—H9 | 109.4 | C8—O26—H26 | 109.5 |
O32—C10—C1 | 102.12 (18) | C9—O27—C7 | 106.29 (17) |
O32—C10—C19 | 108.4 (2) | C4—C28—H28A | 109.5 |
C1—C10—C19 | 110.9 (2) | C4—C28—H28B | 109.5 |
O32—C10—C5 | 110.5 (2) | H28A—C28—H28B | 109.5 |
C1—C10—C5 | 110.65 (19) | C4—C28—H28C | 109.5 |
C19—C10—C5 | 113.6 (2) | H28A—C28—H28C | 109.5 |
C9—C11—C12 | 109.3 (2) | H28B—C28—H28C | 109.5 |
C9—C11—H11A | 109.8 | C4—C29—H29A | 109.5 |
C12—C11—H11A | 109.8 | C4—C29—H29B | 109.5 |
C9—C11—H11B | 109.8 | H29A—C29—H29B | 109.5 |
C12—C11—H11B | 109.8 | C4—C29—H29C | 109.5 |
H11A—C11—H11B | 108.3 | H29A—C29—H29C | 109.5 |
C13—C12—C11 | 116.26 (17) | H29B—C29—H29C | 109.5 |
C13—C12—H12A | 108.2 | C8—C30—C7 | 103.46 (19) |
C11—C12—H12A | 108.2 | C8—C30—H30A | 111.1 |
C13—C12—H12B | 108.2 | C7—C30—H30A | 111.1 |
C11—C12—H12B | 108.2 | C8—C30—H30B | 111.1 |
H12A—C12—H12B | 107.4 | C7—C30—H30B | 111.1 |
C18—C13—C17 | 116.8 (2) | H30A—C30—H30B | 109.0 |
C18—C13—C14 | 59.95 (14) | C7—O31—C4 | 111.55 (19) |
C17—C13—C14 | 105.25 (18) | C3—O32—C10 | 110.2 (2) |
| | | |
C10—C1—C2—C3 | 2.0 (3) | C8—C14—C15—O25 | 45.0 (4) |
C1—C2—C3—O33 | 177.4 (3) | C13—C14—C15—O25 | 179.3 (3) |
C1—C2—C3—O32 | −2.0 (3) | C18—C14—C15—O16 | 60.4 (3) |
O31—C4—C5—C6 | −13.5 (2) | C8—C14—C15—O16 | −136.7 (2) |
C29—C4—C5—C6 | −129.6 (2) | C13—C14—C15—O16 | −2.4 (3) |
C28—C4—C5—C6 | 100.1 (3) | O25—C15—O16—C17 | −170.9 (3) |
O31—C4—C5—C10 | −140.6 (2) | C14—C15—O16—C17 | 10.7 (3) |
C29—C4—C5—C10 | 103.4 (3) | C15—O16—C17—C20 | −142.1 (2) |
C28—C4—C5—C10 | −26.9 (4) | C15—O16—C17—C13 | −14.5 (3) |
C10—C5—C6—C7 | 160.3 (2) | C18—C13—C17—O16 | −51.5 (2) |
C4—C5—C6—C7 | 29.4 (2) | C14—C13—C17—O16 | 12.2 (2) |
C5—C6—C7—O31 | −35.1 (2) | C12—C13—C17—O16 | 151.3 (2) |
C5—C6—C7—O27 | 83.2 (2) | C18—C13—C17—C20 | 70.2 (3) |
C5—C6—C7—C30 | −155.1 (2) | C14—C13—C17—C20 | 133.8 (2) |
O26—C8—C9—O27 | −71.4 (2) | C12—C13—C17—C20 | −87.0 (3) |
C14—C8—C9—O27 | 173.78 (17) | C17—C13—C18—C14 | 92.8 (2) |
C30—C8—C9—O27 | 45.7 (2) | C12—C13—C18—C14 | −110.1 (2) |
O26—C8—C9—C11 | 51.6 (2) | C15—C14—C18—C13 | −96.2 (2) |
C14—C8—C9—C11 | −63.2 (2) | C8—C14—C18—C13 | 102.8 (2) |
C30—C8—C9—C11 | 168.69 (19) | O16—C17—C20—C22 | 121.1 (3) |
C2—C1—C10—O32 | −1.2 (3) | C13—C17—C20—C22 | 0.9 (4) |
C2—C1—C10—C19 | 114.1 (3) | O16—C17—C20—C21 | −60.9 (3) |
C2—C1—C10—C5 | −118.8 (3) | C13—C17—C20—C21 | 178.8 (2) |
C6—C5—C10—O32 | −62.4 (3) | C22—C20—C21—C23 | 0.3 (3) |
C4—C5—C10—O32 | 60.5 (3) | C17—C20—C21—C23 | −178.1 (3) |
C6—C5—C10—C1 | 50.0 (3) | C21—C20—C22—O24 | −0.6 (3) |
C4—C5—C10—C1 | 172.9 (2) | C17—C20—C22—O24 | 177.6 (2) |
C6—C5—C10—C19 | 175.5 (2) | C20—C21—C23—O24 | 0.2 (4) |
C4—C5—C10—C19 | −61.6 (3) | C20—C22—O24—C23 | 0.7 (3) |
O27—C9—C11—C12 | 179.6 (2) | C21—C23—O24—C22 | −0.5 (4) |
C8—C9—C11—C12 | 63.9 (3) | C11—C9—O27—C7 | −163.94 (19) |
C9—C11—C12—C13 | −36.9 (3) | C8—C9—O27—C7 | −43.4 (2) |
C11—C12—C13—C18 | 81.8 (3) | O31—C7—O27—C9 | −93.8 (2) |
C11—C12—C13—C17 | −121.6 (2) | C6—C7—O27—C9 | 151.35 (19) |
C11—C12—C13—C14 | 11.3 (4) | C30—C7—O27—C9 | 22.9 (2) |
O26—C8—C14—C15 | 46.8 (2) | O26—C8—C30—C7 | 83.8 (2) |
C30—C8—C14—C15 | −80.4 (3) | C14—C8—C30—C7 | −151.90 (19) |
C9—C8—C14—C15 | 163.8 (2) | C9—C8—C30—C7 | −30.9 (2) |
O26—C8—C14—C18 | −153.3 (2) | O31—C7—C30—C8 | 124.71 (19) |
C30—C8—C14—C18 | 79.4 (3) | O27—C7—C30—C8 | 6.6 (2) |
C9—C8—C14—C18 | −36.3 (3) | C6—C7—C30—C8 | −117.1 (2) |
O26—C8—C14—C13 | −82.3 (2) | O27—C7—O31—C4 | −90.2 (2) |
C30—C8—C14—C13 | 150.39 (19) | C6—C7—O31—C4 | 28.0 (3) |
C9—C8—C14—C13 | 34.6 (3) | C30—C7—O31—C4 | 154.34 (19) |
C18—C13—C14—C15 | 106.1 (2) | C29—C4—O31—C7 | 109.4 (3) |
C17—C13—C14—C15 | −6.3 (3) | C28—C4—O31—C7 | −132.6 (2) |
C12—C13—C14—C15 | −145.0 (2) | C5—C4—O31—C7 | −8.9 (3) |
C17—C13—C14—C18 | −112.5 (2) | O33—C3—O32—C10 | −178.3 (3) |
C12—C13—C14—C18 | 108.8 (2) | C2—C3—O32—C10 | 1.2 (3) |
C18—C13—C14—C8 | −119.1 (2) | C1—C10—O32—C3 | −0.1 (3) |
C17—C13—C14—C8 | 128.4 (2) | C19—C10—O32—C3 | −117.2 (2) |
C12—C13—C14—C8 | −10.3 (3) | C5—C10—O32—C3 | 117.7 (2) |
C18—C14—C15—O25 | −117.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28C···O32 | 0.96 | 2.41 | 2.894 (4) | 111 |
O26—H26···O25i | 0.82 | 2.00 | 2.805 (2) | 169 |
C23—H23···O31ii | 0.93 | 2.43 | 3.283 (3) | 152 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+2; (ii) −x+2, y−1/2, −z+5/2. |
Experimental details
Crystal data |
Chemical formula | C25H28O8 |
Mr | 456.47 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 7.224 (2), 15.521 (2), 20.404 (1) |
V (Å3) | 2287.8 (7) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.82 |
Crystal size (mm) | 0.25 × 0.25 × 0.20 |
|
Data collection |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2417, 2417, 2171 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.609 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.092, 1.04 |
No. of reflections | 2417 |
No. of parameters | 303 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.17 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28C···O32 | 0.96 | 2.41 | 2.894 (4) | 110.5 |
O26—H26···O25i | 0.82 | 2.00 | 2.805 (2) | 168.6 |
C23—H23···O31ii | 0.93 | 2.43 | 3.283 (3) | 151.7 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+2; (ii) −x+2, y−1/2, −z+5/2. |
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The molecular structure of tricoccin R6, (I), is shown in Fig. 1. The bond geometry conforms to expectations. The puckering parameters evaluated using PARST97 (Nardelli, 1995) show that (i) both the terminal five-membered rings (A and F) are planar, (ii) the fused five-membered ring B is in a slightly distorted half-chair conformation, and rings C and E are in envelope conformations [q2 = 0.334 (2) Å, ϕ2 = -119.7 (4)° for ring B, q2 = 0.440 (2) Å, ϕ2 = -134.7 (3)° for ring C, and q2 = 0.129 (2) Å, ϕ2 = 151.2 (11)° for ring E]. The six-membered ring D has a slightly distorted sofa conformation [q2 = 0.369 (3), q3 = 0.364 (3), QT = 0.519 (2) Å, ϕ2 = 63.0 (4)°]. Fig. 2 shows the packing diagram of the molecules. The structure is stabilized by intermolecular O—H···O hydrogen bonds and C—H—O inter- and intramolecular interactions (see Table 1).