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In the mol­ecule of the title compound (systematic name: 1α-hydr­oxy-6β,7β-diacet­oxy-8,13-epoxy­labd-14-en-11-one), C24H36O7, rings A and B adopt chair conformations, while ring C has a twist–boat conformation. The crystal structure is stabilized by inter­molecular O—H...O and C—H...O hydrogen bonds, linking the mol­ecules into networks approximately parallel to the (110) plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018095/hk2036sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018095/hk2036Isup2.hkl
Contains datablock I

CCDC reference: 610807

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.035
  • wR factor = 0.093
  • Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack parameter is too small From the CIF: _refine_ls_abs_structure_Flack -10.000 From the CIF: _refine_ls_abs_structure_Flack_su 10.000 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... -10.00 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.55 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H12A .. O5 .. 2.61 Ang.
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 25.01 From the CIF: _reflns_number_total 2168 Count of symmetry unique reflns 2168 Completeness (_total/calc) 100.00% 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 7 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1α-hydroxy-6β,7β-diacetoxy-8,13-epoxylabd-14-en-11-one top
Crystal data top
C24H36O7F(000) = 472
Mr = 436.53Dx = 1.244 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2946 reflections
a = 9.839 (3) Åθ = 2.3–28.3°
b = 11.981 (4) ŵ = 0.09 mm1
c = 10.908 (4) ÅT = 298 K
β = 114.982 (4)°Prism, colourless
V = 1165.5 (7) Å30.48 × 0.45 × 0.40 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
2168 independent reflections
Radiation source: fine-focus sealed tube1884 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1111
Tmin = 0.958, Tmax = 0.965k = 1413
6139 measured reflectionsl = 129
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.051P)2 + 0.222P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.016
2168 reflectionsΔρmax = 0.17 e Å3
287 parametersΔρmin = 0.15 e Å3
1 restraintAbsolute structure: Flack (1983), with no Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 10 (10)
Special details top

Experimental. IR (KBr, νmax, cm-1): 3444, 2954, 1734, 1238 and 1035.

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
xyzUiso*/Ueq
O10.7072 (2)0.6729 (2)0.5857 (2)0.0549 (6)
H1B0.78620.67490.57730.082*
O20.20973 (18)0.79428 (17)0.61815 (19)0.0383 (4)
O30.0112 (2)0.7053 (2)0.5518 (2)0.0591 (6)
O40.2637 (2)0.64237 (18)0.81966 (19)0.0429 (5)
O50.2023 (3)0.4652 (2)0.7561 (3)0.0817 (9)
O60.5783 (2)0.6281 (2)0.9591 (2)0.0496 (5)
O70.8311 (3)0.8470 (3)0.8518 (2)0.0749 (8)
C10.6447 (3)0.7834 (3)0.5693 (3)0.0436 (7)
H1A0.72610.83650.61590.052*
C20.5705 (3)0.8135 (3)0.4200 (3)0.0507 (8)
H2A0.64380.80840.38250.061*
H2B0.53520.89000.41020.061*
C30.4395 (3)0.7369 (3)0.3417 (3)0.0468 (7)
H3A0.47670.66130.34650.056*
H3B0.39540.75920.24740.056*
C40.3167 (3)0.7378 (3)0.3944 (3)0.0407 (6)
C50.3959 (3)0.7122 (2)0.5500 (2)0.0326 (6)
H50.44040.63840.55350.039*
C60.2871 (3)0.6918 (2)0.6156 (3)0.0346 (6)
H60.21220.63690.56070.042*
C70.3677 (3)0.6457 (3)0.7577 (3)0.0365 (6)
H70.39810.56890.75090.044*
C80.5072 (3)0.7100 (3)0.8537 (3)0.0381 (6)
C90.6092 (3)0.7302 (2)0.7789 (3)0.0360 (6)
H90.63680.65530.76120.043*
C100.5343 (3)0.7862 (2)0.6376 (3)0.0357 (6)
C110.7554 (3)0.7810 (3)0.8804 (3)0.0466 (7)
C120.8043 (3)0.7459 (3)1.0257 (3)0.0538 (8)
H12A0.78570.80781.07380.065*
H12B0.91180.73401.06470.065*
C130.7320 (3)0.6421 (3)1.0533 (3)0.0448 (7)
C140.2081 (3)0.6423 (3)0.3235 (3)0.0526 (8)
H14A0.12000.64920.34010.079*
H14B0.25600.57210.35820.079*
H14C0.18020.64580.22800.079*
C150.2284 (4)0.8477 (3)0.3531 (3)0.0584 (9)
H15A0.29420.90910.39520.088*
H15B0.14850.84670.38160.088*
H15C0.18730.85590.25660.088*
C160.0614 (3)0.7906 (3)0.5836 (3)0.0426 (7)
C170.0015 (3)0.9025 (3)0.5902 (4)0.0610 (9)
H17A0.06480.95850.57850.091*
H17B0.00100.91220.67660.091*
H17C0.09810.90950.51990.091*
C180.1878 (3)0.5480 (3)0.8103 (3)0.0515 (8)
C190.0802 (4)0.5621 (4)0.8742 (5)0.0745 (11)
H19A0.12310.61130.95040.112*
H19B0.06100.49070.90370.112*
H19C0.01210.59310.80920.112*
C200.4659 (3)0.8132 (3)0.9125 (3)0.0493 (8)
H20A0.55080.86230.94910.074*
H20B0.43730.79110.98280.074*
H20C0.38380.85110.84240.074*
C210.4984 (3)0.9098 (2)0.6492 (3)0.0442 (7)
H21A0.48770.94880.56880.066*
H21B0.57860.94260.72620.066*
H21C0.40670.91510.66000.066*
C220.8180 (4)0.5406 (3)1.0472 (3)0.0521 (8)
H220.91940.53921.10590.062*
C230.7666 (5)0.4541 (3)0.9690 (4)0.0662 (10)
H23A0.66600.45110.90830.079*
H23B0.83030.39530.97370.079*
C240.7326 (4)0.6500 (4)1.1936 (3)0.0634 (9)
H24A0.67770.71501.19780.095*
H24B0.83400.65531.26110.095*
H24C0.68620.58461.20990.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0400 (10)0.0671 (16)0.0689 (14)0.0090 (10)0.0339 (10)0.0034 (11)
O20.0271 (8)0.0402 (11)0.0506 (11)0.0002 (8)0.0194 (8)0.0004 (9)
O30.0328 (10)0.0574 (15)0.0889 (17)0.0061 (11)0.0274 (11)0.0112 (13)
O40.0364 (9)0.0509 (12)0.0504 (11)0.0049 (10)0.0270 (9)0.0016 (10)
O50.100 (2)0.0532 (16)0.125 (2)0.0224 (15)0.0793 (19)0.0135 (17)
O60.0370 (10)0.0609 (14)0.0444 (11)0.0075 (10)0.0108 (9)0.0085 (10)
O70.0511 (13)0.103 (2)0.0638 (15)0.0388 (15)0.0174 (11)0.0001 (15)
C10.0376 (14)0.0467 (17)0.0545 (17)0.0044 (14)0.0272 (13)0.0014 (14)
C20.0519 (17)0.057 (2)0.0570 (19)0.0044 (15)0.0365 (15)0.0045 (15)
C30.0456 (16)0.059 (2)0.0401 (15)0.0030 (15)0.0222 (13)0.0044 (14)
C40.0341 (13)0.0491 (17)0.0395 (14)0.0029 (13)0.0161 (12)0.0028 (13)
C50.0284 (11)0.0343 (15)0.0380 (14)0.0019 (11)0.0168 (11)0.0004 (11)
C60.0260 (11)0.0357 (15)0.0423 (14)0.0026 (11)0.0144 (11)0.0022 (12)
C70.0319 (12)0.0411 (15)0.0437 (14)0.0016 (12)0.0231 (11)0.0000 (13)
C80.0313 (12)0.0455 (17)0.0369 (14)0.0051 (13)0.0137 (11)0.0005 (12)
C90.0280 (12)0.0393 (15)0.0421 (15)0.0029 (12)0.0160 (11)0.0008 (12)
C100.0285 (12)0.0387 (16)0.0427 (15)0.0033 (12)0.0178 (11)0.0006 (13)
C110.0311 (13)0.057 (2)0.0506 (17)0.0080 (15)0.0162 (13)0.0046 (15)
C120.0393 (15)0.063 (2)0.0497 (18)0.0077 (15)0.0100 (14)0.0075 (16)
C130.0344 (13)0.0612 (19)0.0352 (14)0.0025 (15)0.0112 (11)0.0037 (15)
C140.0421 (15)0.068 (2)0.0434 (16)0.0026 (16)0.0145 (13)0.0073 (16)
C150.0571 (19)0.068 (2)0.0521 (19)0.0198 (18)0.0248 (16)0.0154 (17)
C160.0301 (13)0.0527 (19)0.0472 (16)0.0012 (14)0.0185 (12)0.0024 (15)
C170.0395 (15)0.062 (2)0.085 (3)0.0076 (16)0.0300 (17)0.0083 (19)
C180.0454 (17)0.056 (2)0.060 (2)0.0091 (16)0.0298 (16)0.0066 (17)
C190.067 (2)0.083 (3)0.099 (3)0.009 (2)0.060 (2)0.009 (2)
C200.0454 (15)0.056 (2)0.0517 (17)0.0055 (15)0.0252 (14)0.0110 (15)
C210.0444 (15)0.0375 (17)0.0546 (18)0.0055 (13)0.0246 (14)0.0018 (13)
C220.0463 (17)0.062 (2)0.0498 (18)0.0009 (16)0.0223 (15)0.0005 (16)
C230.073 (2)0.067 (2)0.070 (2)0.003 (2)0.041 (2)0.006 (2)
C240.062 (2)0.083 (3)0.0411 (16)0.001 (2)0.0185 (15)0.0078 (18)
Geometric parameters (Å, º) top
O1—C11.439 (4)C10—C211.540 (4)
O1—H1B0.8200C11—C121.509 (4)
O2—C161.345 (3)C12—C131.524 (5)
O2—C61.451 (3)C12—H12A0.9700
O3—C161.210 (4)C12—H12B0.9700
O4—C181.336 (4)C13—C221.499 (5)
O4—C71.445 (3)C13—C241.531 (4)
O5—C181.193 (4)C14—H14A0.9600
O6—C131.435 (3)C14—H14B0.9600
O6—C81.447 (3)C14—H14C0.9600
O7—C111.213 (4)C15—H15A0.9600
C1—C21.520 (4)C15—H15B0.9600
C1—C101.556 (4)C15—H15C0.9600
C1—H1A0.9800C16—C171.479 (5)
C2—C31.518 (5)C17—H17A0.9600
C2—H2A0.9700C17—H17B0.9600
C2—H2B0.9700C17—H17C0.9600
C3—C41.541 (4)C18—C191.502 (5)
C3—H3A0.9700C19—H19A0.9600
C3—H3B0.9700C19—H19B0.9600
C4—C141.533 (4)C19—H19C0.9600
C4—C151.536 (4)C20—H20A0.9600
C4—C51.571 (4)C20—H20B0.9600
C5—C61.537 (3)C20—H20C0.9600
C5—C101.567 (4)C21—H21A0.9600
C5—H50.9800C21—H21B0.9600
C6—C71.516 (4)C21—H21C0.9600
C6—H60.9800C22—C231.301 (5)
C7—C81.536 (4)C22—H220.9300
C7—H70.9800C23—H23A0.9300
C8—C201.524 (4)C23—H23B0.9300
C8—C91.557 (4)C24—H24A0.9600
C9—C111.523 (4)C24—H24B0.9600
C9—C101.553 (4)C24—H24C0.9600
C9—H90.9800
C1—O1—H1B109.5C11—C12—C13117.8 (3)
C16—O2—C6118.8 (2)C11—C12—H12A107.8
C18—O4—C7118.1 (2)C13—C12—H12A107.8
C13—O6—C8120.0 (2)C11—C12—H12B107.8
O1—C1—C2109.8 (3)C13—C12—H12B107.8
O1—C1—C10107.9 (2)H12A—C12—H12B107.2
C2—C1—C10113.0 (2)O6—C13—C22108.5 (3)
O1—C1—H1A108.7O6—C13—C12113.1 (2)
C2—C1—H1A108.7C22—C13—C12109.5 (2)
C10—C1—H1A108.7O6—C13—C24106.3 (2)
C1—C2—C3111.6 (3)C22—C13—C24109.3 (3)
C1—C2—H2A109.3C12—C13—C24110.0 (3)
C3—C2—H2A109.3C4—C14—H14A109.5
C1—C2—H2B109.3C4—C14—H14B109.5
C3—C2—H2B109.3H14A—C14—H14B109.5
H2A—C2—H2B108.0C4—C14—H14C109.5
C2—C3—C4113.5 (3)H14A—C14—H14C109.5
C2—C3—H3A108.9H14B—C14—H14C109.5
C4—C3—H3A108.9C4—C15—H15A109.5
C2—C3—H3B108.9C4—C15—H15B109.5
C4—C3—H3B108.9H15A—C15—H15B109.5
H3A—C3—H3B107.7C4—C15—H15C109.5
C14—C4—C15107.7 (2)H15A—C15—H15C109.5
C14—C4—C3107.2 (3)H15B—C15—H15C109.5
C15—C4—C3109.4 (3)O3—C16—O2123.2 (3)
C14—C4—C5108.7 (2)O3—C16—C17125.5 (2)
C15—C4—C5116.4 (2)O2—C16—C17111.3 (3)
C3—C4—C5107.0 (2)C16—C17—H17A109.5
C6—C5—C10113.8 (2)C16—C17—H17B109.5
C6—C5—C4114.1 (2)H17A—C17—H17B109.5
C10—C5—C4117.1 (2)C16—C17—H17C109.5
C6—C5—H5103.1H17A—C17—H17C109.5
C10—C5—H5103.1H17B—C17—H17C109.5
C4—C5—H5103.1O5—C18—O4124.2 (3)
O2—C6—C7109.9 (2)O5—C18—C19125.3 (3)
O2—C6—C5110.4 (2)O4—C18—C19110.5 (3)
C7—C6—C5111.55 (19)C18—C19—H19A109.5
O2—C6—H6108.3C18—C19—H19B109.5
C7—C6—H6108.3H19A—C19—H19B109.5
C5—C6—H6108.3C18—C19—H19C109.5
O4—C7—C6108.7 (2)H19A—C19—H19C109.5
O4—C7—C8107.5 (2)H19B—C19—H19C109.5
C6—C7—C8116.5 (2)C8—C20—H20A109.5
O4—C7—H7108.0C8—C20—H20B109.5
C6—C7—H7108.0H20A—C20—H20B109.5
C8—C7—H7108.0C8—C20—H20C109.5
O6—C8—C20109.9 (2)H20A—C20—H20C109.5
O6—C8—C7101.2 (2)H20B—C20—H20C109.5
C20—C8—C7111.9 (2)C10—C21—H21A109.5
O6—C8—C9108.6 (2)C10—C21—H21B109.5
C20—C8—C9116.1 (2)H21A—C21—H21B109.5
C7—C8—C9108.0 (2)C10—C21—H21C109.5
C11—C9—C10117.1 (2)H21A—C21—H21C109.5
C11—C9—C8107.6 (2)H21B—C21—H21C109.5
C10—C9—C8116.53 (19)C23—C22—C13127.2 (3)
C11—C9—H9104.7C23—C22—H22116.4
C10—C9—H9104.7C13—C22—H22116.4
C8—C9—H9104.7C22—C23—H23A120.0
C21—C10—C9111.3 (2)C22—C23—H23B120.0
C21—C10—C1106.9 (2)H23A—C23—H23B120.0
C9—C10—C1109.4 (2)C13—C24—H24A109.5
C21—C10—C5115.1 (2)C13—C24—H24B109.5
C9—C10—C5106.7 (2)H24A—C24—H24B109.5
C1—C10—C5107.4 (2)C13—C24—H24C109.5
O7—C11—C12119.6 (3)H24A—C24—H24C109.5
O7—C11—C9124.6 (3)H24B—C24—H24C109.5
C12—C11—C9115.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O3i0.822.162.972 (3)172
C12—H12A···O5ii0.972.613.564 (5)167
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1/2, z+2.
 

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