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organic compounds
The title compound, C19H18O5, is a diastereoisomer of crotocaudin, both being isolated from the plants of genus Croton. In isocrotocaudin, the furan moiety makes a dihedral angle with the adjacent lactone of 13.53 (17)°. The cyclohexyl ring of the diterpene moiety adopts a chair confirmation. The weak intermolecular C—HO hydrogen bonds link the molecules into linear chains along the c axis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007725/cv6464sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007725/cv6464Isup2.hkl |
CCDC reference: 270285
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.056
- wR factor = 0.113
- Data-to-parameter ratio = 8.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 1866 Count of symmetry unique reflns 1872 Completeness (_total/calc) 99.68% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
ent-(8S,10R)-15,16-epoxy-19-norcleroda-4,11,13 (16),14-tetraene- 18,6(R):20,12-diolactone top
Crystal data top
C19H18O5 | Dx = 1.330 Mg m−3 |
Mr = 326.33 | Melting point = 485.5–486.8 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 743 reflections |
a = 6.677 (2) Å | θ = 1.8–26.0° |
b = 10.794 (3) Å | µ = 0.10 mm−1 |
c = 22.608 (7) Å | T = 298 K |
V = 1629.4 (8) Å3 | Slab, colourless |
Z = 4 | 0.42 × 0.10 × 0.09 mm |
F(000) = 688 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1866 independent reflections |
Radiation source: fine-focus sealed tube | 1583 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→13 |
Tmin = 0.960, Tmax = 0.991 | l = −18→27 |
8831 measured reflections |
Refinement top
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0462P)2 + 0.3404P] where P = (Fo2 + 2Fc2)/3 |
1866 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 1.1679 (6) | 0.3232 (3) | 0.44225 (11) | 0.0774 (9) | |
O2 | 0.8829 (4) | 0.3716 (2) | 0.27849 (9) | 0.0481 (6) | |
O3 | 0.6987 (4) | 0.4292 (2) | 0.20096 (10) | 0.0521 (6) | |
O4 | 0.6785 (4) | 0.2900 (3) | 0.01985 (10) | 0.0605 (7) | |
O5 | 0.7258 (5) | 0.4628 (3) | −0.03299 (12) | 0.0869 (10) | |
C1 | 1.1822 (5) | 0.4127 (3) | 0.15144 (14) | 0.0475 (9) | |
H1A | 1.0990 | 0.4719 | 0.1724 | 0.057* | |
H1B | 1.2949 | 0.3921 | 0.1767 | 0.057* | |
C2 | 1.2589 (6) | 0.4714 (4) | 0.09482 (16) | 0.0605 (11) | |
H2A | 1.3413 | 0.4120 | 0.0738 | 0.073* | |
H2B | 1.3421 | 0.5421 | 0.1046 | 0.073* | |
C3 | 1.0880 (6) | 0.5137 (3) | 0.05458 (16) | 0.0573 (10) | |
H3A | 1.0265 | 0.5879 | 0.0705 | 0.069* | |
H3B | 1.1393 | 0.5325 | 0.0155 | 0.069* | |
C4 | 0.9381 (5) | 0.4130 (3) | 0.05087 (13) | 0.0418 (8) | |
C5 | 0.9356 (5) | 0.3159 (3) | 0.08600 (13) | 0.0352 (7) | |
C6 | 0.7800 (5) | 0.2275 (3) | 0.06742 (14) | 0.0457 (8) | |
H6A | 0.8441 | 0.1524 | 0.0521 | 0.055* | |
C7 | 0.6461 (5) | 0.1936 (3) | 0.11863 (15) | 0.0512 (9) | |
H7A | 0.5567 | 0.1270 | 0.1070 | 0.061* | |
H7B | 0.5652 | 0.2645 | 0.1297 | 0.061* | |
C8 | 0.7728 (5) | 0.1523 (3) | 0.17134 (15) | 0.0451 (8) | |
H8A | 0.8488 | 0.0793 | 0.1587 | 0.054* | |
C9 | 0.9281 (5) | 0.2511 (3) | 0.19197 (12) | 0.0351 (7) | |
C10 | 1.0609 (5) | 0.2958 (3) | 0.13902 (12) | 0.0343 (7) | |
H10A | 1.1558 | 0.2292 | 0.1298 | 0.041* | |
C11 | 1.0549 (5) | 0.2085 (3) | 0.24245 (13) | 0.0399 (8) | |
H11A | 1.1413 | 0.1410 | 0.2411 | 0.048* | |
C12 | 1.0280 (5) | 0.2792 (3) | 0.28895 (13) | 0.0406 (8) | |
C13 | 1.1131 (6) | 0.2818 (3) | 0.34758 (14) | 0.0461 (9) | |
C14 | 1.2892 (7) | 0.2164 (4) | 0.36677 (16) | 0.0648 (11) | |
H14A | 1.3705 | 0.1651 | 0.3440 | 0.078* | |
C15 | 1.3119 (8) | 0.2442 (5) | 0.42338 (18) | 0.0803 (14) | |
H15A | 1.4139 | 0.2134 | 0.4472 | 0.096* | |
C16 | 1.0483 (7) | 0.3431 (3) | 0.39508 (15) | 0.0578 (10) | |
H16A | 0.9351 | 0.3933 | 0.3956 | 0.069* | |
C17 | 0.6363 (6) | 0.1112 (4) | 0.22187 (18) | 0.0735 (13) | |
H17A | 0.5439 | 0.0499 | 0.2077 | 0.110* | |
H17B | 0.5632 | 0.1814 | 0.2366 | 0.110* | |
H17C | 0.7158 | 0.0766 | 0.2531 | 0.110* | |
C18 | 0.7761 (6) | 0.3981 (4) | 0.00767 (15) | 0.0551 (10) | |
C20 | 0.8209 (5) | 0.3598 (3) | 0.22091 (14) | 0.0396 (8) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.103 (2) | 0.0812 (19) | 0.0479 (15) | 0.003 (2) | −0.0166 (17) | −0.0192 (15) |
O2 | 0.0579 (15) | 0.0499 (13) | 0.0366 (12) | 0.0154 (12) | 0.0067 (12) | −0.0020 (10) |
O3 | 0.0464 (15) | 0.0536 (14) | 0.0562 (14) | 0.0220 (13) | 0.0030 (12) | 0.0064 (12) |
O4 | 0.0562 (16) | 0.0787 (18) | 0.0465 (14) | −0.0022 (15) | −0.0208 (13) | −0.0024 (13) |
O5 | 0.091 (2) | 0.109 (2) | 0.0610 (17) | 0.011 (2) | −0.0216 (18) | 0.0279 (17) |
C1 | 0.037 (2) | 0.057 (2) | 0.0481 (19) | −0.0058 (18) | −0.0007 (17) | −0.0065 (17) |
C2 | 0.049 (2) | 0.071 (2) | 0.062 (2) | −0.019 (2) | 0.009 (2) | 0.0009 (19) |
C3 | 0.065 (3) | 0.053 (2) | 0.054 (2) | −0.006 (2) | 0.011 (2) | 0.0079 (18) |
C4 | 0.0427 (19) | 0.0497 (19) | 0.0329 (16) | 0.0080 (18) | 0.0041 (16) | −0.0027 (15) |
C5 | 0.0274 (17) | 0.0431 (17) | 0.0350 (16) | 0.0041 (15) | 0.0031 (14) | −0.0062 (14) |
C6 | 0.043 (2) | 0.0515 (19) | 0.0426 (19) | 0.0014 (17) | −0.0080 (16) | −0.0078 (15) |
C7 | 0.037 (2) | 0.056 (2) | 0.061 (2) | −0.0103 (18) | −0.0071 (18) | −0.0017 (18) |
C8 | 0.040 (2) | 0.0392 (17) | 0.056 (2) | −0.0004 (16) | 0.0006 (17) | 0.0049 (16) |
C9 | 0.0342 (17) | 0.0372 (15) | 0.0338 (16) | 0.0073 (15) | 0.0007 (14) | −0.0011 (13) |
C10 | 0.0283 (16) | 0.0393 (16) | 0.0352 (16) | 0.0036 (15) | −0.0006 (13) | −0.0050 (13) |
C11 | 0.0379 (19) | 0.0416 (16) | 0.0403 (18) | 0.0101 (16) | 0.0005 (15) | 0.0011 (15) |
C12 | 0.0426 (19) | 0.0402 (17) | 0.0390 (18) | 0.0041 (16) | 0.0081 (16) | 0.0036 (14) |
C13 | 0.059 (2) | 0.0472 (19) | 0.0317 (17) | −0.0014 (18) | −0.0026 (17) | −0.0016 (15) |
C14 | 0.060 (3) | 0.082 (3) | 0.052 (2) | 0.011 (2) | −0.012 (2) | −0.007 (2) |
C15 | 0.078 (3) | 0.104 (3) | 0.059 (3) | 0.007 (3) | −0.026 (3) | −0.008 (3) |
C16 | 0.076 (3) | 0.053 (2) | 0.045 (2) | 0.000 (2) | −0.008 (2) | −0.0016 (18) |
C17 | 0.054 (2) | 0.085 (3) | 0.081 (3) | −0.019 (2) | −0.002 (2) | 0.037 (2) |
C18 | 0.058 (2) | 0.069 (3) | 0.038 (2) | 0.014 (2) | −0.0016 (19) | −0.0009 (18) |
C20 | 0.0375 (18) | 0.0431 (17) | 0.0383 (17) | 0.0029 (16) | 0.0114 (16) | 0.0049 (14) |
Geometric parameters (Å, º) top
O1—C16 | 1.350 (5) | C6—H6A | 0.9800 |
O1—C15 | 1.354 (5) | C7—C8 | 1.528 (5) |
O2—C20 | 1.372 (4) | C7—H7A | 0.9700 |
O2—C12 | 1.411 (4) | C7—H7B | 0.9700 |
O3—C20 | 1.196 (4) | C8—C17 | 1.527 (5) |
O4—C18 | 1.365 (5) | C8—C9 | 1.559 (4) |
O4—C6 | 1.439 (4) | C8—H8A | 0.9800 |
O5—C18 | 1.202 (4) | C9—C11 | 1.494 (4) |
C1—C2 | 1.517 (5) | C9—C20 | 1.522 (4) |
C1—C10 | 1.526 (4) | C9—C10 | 1.566 (4) |
C1—H1A | 0.9700 | C10—H10A | 0.9800 |
C1—H1B | 0.9700 | C11—C12 | 1.312 (4) |
C2—C3 | 1.529 (5) | C11—H11A | 0.9300 |
C2—H2A | 0.9700 | C12—C13 | 1.442 (4) |
C2—H2B | 0.9700 | C13—C16 | 1.334 (5) |
C3—C4 | 1.480 (5) | C13—C14 | 1.439 (6) |
C3—H3A | 0.9700 | C14—C15 | 1.323 (5) |
C3—H3B | 0.9700 | C14—H14A | 0.9300 |
C4—C5 | 1.316 (4) | C15—H15A | 0.9300 |
C4—C18 | 1.466 (5) | C16—H16A | 0.9300 |
C5—C6 | 1.471 (4) | C17—H17A | 0.9600 |
C5—C10 | 1.478 (4) | C17—H17B | 0.9600 |
C6—C7 | 1.508 (5) | C17—H17C | 0.9600 |
C16—O1—C15 | 105.8 (3) | C9—C8—H8A | 107.1 |
C20—O2—C12 | 107.5 (2) | C11—C9—C20 | 100.1 (2) |
C18—O4—C6 | 109.1 (3) | C11—C9—C8 | 113.3 (2) |
C2—C1—C10 | 111.7 (3) | C20—C9—C8 | 110.1 (3) |
C2—C1—H1A | 109.3 | C11—C9—C10 | 111.0 (3) |
C10—C1—H1A | 109.3 | C20—C9—C10 | 110.9 (2) |
C2—C1—H1B | 109.3 | C8—C9—C10 | 111.0 (2) |
C10—C1—H1B | 109.3 | C5—C10—C1 | 109.2 (2) |
H1A—C1—H1B | 107.9 | C5—C10—C9 | 110.1 (3) |
C1—C2—C3 | 112.0 (3) | C1—C10—C9 | 114.5 (2) |
C1—C2—H2A | 109.2 | C5—C10—H10A | 107.6 |
C3—C2—H2A | 109.2 | C1—C10—H10A | 107.6 |
C1—C2—H2B | 109.2 | C9—C10—H10A | 107.6 |
C3—C2—H2B | 109.2 | C12—C11—C9 | 110.8 (3) |
H2A—C2—H2B | 107.9 | C12—C11—H11A | 124.6 |
C4—C3—C2 | 108.6 (3) | C9—C11—H11A | 124.6 |
C4—C3—H3A | 110.0 | C11—C12—O2 | 111.8 (3) |
C2—C3—H3A | 110.0 | C11—C12—C13 | 134.0 (3) |
C4—C3—H3B | 110.0 | O2—C12—C13 | 114.3 (3) |
C2—C3—H3B | 110.0 | C16—C13—C14 | 105.4 (3) |
H3A—C3—H3B | 108.3 | C16—C13—C12 | 128.5 (4) |
C5—C4—C18 | 107.8 (3) | C14—C13—C12 | 126.1 (3) |
C5—C4—C3 | 124.0 (3) | C15—C14—C13 | 105.9 (4) |
C18—C4—C3 | 128.1 (3) | C15—C14—H14A | 127.1 |
C4—C5—C6 | 110.7 (3) | C13—C14—H14A | 127.1 |
C4—C5—C10 | 126.8 (3) | C14—C15—O1 | 111.5 (4) |
C6—C5—C10 | 122.4 (3) | C14—C15—H15A | 124.3 |
O4—C6—C5 | 104.0 (3) | O1—C15—H15A | 124.3 |
O4—C6—C7 | 114.1 (3) | C13—C16—O1 | 111.4 (4) |
C5—C6—C7 | 110.9 (3) | C13—C16—H16A | 124.3 |
O4—C6—H6A | 109.2 | O1—C16—H16A | 124.3 |
C5—C6—H6A | 109.2 | C8—C17—H17A | 109.5 |
C7—C6—H6A | 109.2 | C8—C17—H17B | 109.5 |
C6—C7—C8 | 110.0 (3) | H17A—C17—H17B | 109.5 |
C6—C7—H7A | 109.7 | C8—C17—H17C | 109.5 |
C8—C7—H7A | 109.7 | H17A—C17—H17C | 109.5 |
C6—C7—H7B | 109.7 | H17B—C17—H17C | 109.5 |
C8—C7—H7B | 109.7 | O5—C18—O4 | 121.2 (4) |
H7A—C7—H7B | 108.2 | O5—C18—C4 | 130.7 (4) |
C17—C8—C7 | 109.7 (3) | O4—C18—C4 | 108.2 (3) |
C17—C8—C9 | 111.8 (3) | O3—C20—O2 | 120.4 (3) |
C7—C8—C9 | 113.7 (3) | O3—C20—C9 | 129.9 (3) |
C17—C8—H8A | 107.1 | O2—C20—C9 | 109.7 (3) |
C7—C8—H8A | 107.1 | ||
C10—C1—C2—C3 | 62.5 (4) | C20—C9—C10—C1 | 43.6 (4) |
C1—C2—C3—C4 | −46.3 (4) | C8—C9—C10—C1 | 166.3 (3) |
C2—C3—C4—C5 | 12.6 (5) | C20—C9—C11—C12 | −1.1 (4) |
C2—C3—C4—C18 | −164.1 (3) | C8—C9—C11—C12 | −118.3 (3) |
C18—C4—C5—C6 | 2.6 (4) | C10—C9—C11—C12 | 116.1 (3) |
C3—C4—C5—C6 | −174.7 (3) | C9—C11—C12—O2 | 2.1 (4) |
C18—C4—C5—C10 | −174.7 (3) | C9—C11—C12—C13 | −178.4 (4) |
C3—C4—C5—C10 | 8.1 (5) | C20—O2—C12—C11 | −2.2 (3) |
C18—O4—C6—C5 | 5.5 (3) | C20—O2—C12—C13 | 178.2 (3) |
C18—O4—C6—C7 | 126.5 (3) | C11—C12—C13—C16 | −166.0 (4) |
C4—C5—C6—O4 | −5.0 (4) | O2—C12—C13—C16 | 13.5 (5) |
C10—C5—C6—O4 | 172.4 (3) | C11—C12—C13—C14 | 13.7 (7) |
C4—C5—C6—C7 | −128.1 (3) | O2—C12—C13—C14 | −166.8 (3) |
C10—C5—C6—C7 | 49.3 (4) | C16—C13—C14—C15 | 0.3 (5) |
O4—C6—C7—C8 | −168.6 (3) | C12—C13—C14—C15 | −179.5 (4) |
C5—C6—C7—C8 | −51.5 (4) | C13—C14—C15—O1 | −0.9 (5) |
C6—C7—C8—C17 | −176.9 (3) | C16—O1—C15—C14 | 1.2 (5) |
C6—C7—C8—C9 | 57.0 (4) | C14—C13—C16—O1 | 0.4 (4) |
C17—C8—C9—C11 | 56.6 (4) | C12—C13—C16—O1 | −179.8 (4) |
C7—C8—C9—C11 | −178.4 (3) | C15—O1—C16—C13 | −1.0 (5) |
C17—C8—C9—C20 | −54.5 (4) | C6—O4—C18—O5 | 175.4 (4) |
C7—C8—C9—C20 | 70.4 (3) | C6—O4—C18—C4 | −4.2 (4) |
C17—C8—C9—C10 | −177.8 (3) | C5—C4—C18—O5 | −178.5 (4) |
C7—C8—C9—C10 | −52.8 (3) | C3—C4—C18—O5 | −1.4 (6) |
C4—C5—C10—C1 | 6.0 (4) | C5—C4—C18—O4 | 1.0 (4) |
C6—C5—C10—C1 | −171.0 (3) | C3—C4—C18—O4 | 178.1 (3) |
C4—C5—C10—C9 | 132.5 (3) | C12—O2—C20—O3 | −179.1 (3) |
C6—C5—C10—C9 | −44.4 (4) | C12—O2—C20—C9 | 1.4 (3) |
C2—C1—C10—C5 | −39.7 (4) | C11—C9—C20—O3 | −179.7 (3) |
C2—C1—C10—C9 | −163.7 (3) | C8—C9—C20—O3 | −60.2 (4) |
C11—C9—C10—C5 | 169.8 (2) | C10—C9—C20—O3 | 63.1 (4) |
C20—C9—C10—C5 | −79.9 (3) | C11—C9—C20—O2 | −0.3 (3) |
C8—C9—C10—C5 | 42.9 (3) | C8—C9—C20—O2 | 119.3 (3) |
C11—C9—C10—C1 | −66.8 (3) | C10—C9—C20—O2 | −117.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···O3 | 0.97 | 2.56 | 3.172 (4) | 121 |
C16—H16A···O5i | 0.93 | 2.49 | 3.223 (4) | 136 |
Symmetry code: (i) −x+3/2, −y+1, z+1/2. |
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