Download citation
Download citation
link to html
The relative stereochemistry of ternifoline-C (7,20-epoxy-ent-kaur-16-ene-1,6,7,15-tetrol 1-acetate), C22H32O6, previously reported by Wu [Fudan Xuebao Zir. Kex. (1988), 27, 61-65], has been redetermined at 150 K. The molecular geometry and crystal packing agree well with the previous study.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013032/qa0393sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013032/qa0393Isup2.hkl
Contains datablock I

CCDC reference: 153945

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al.,1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: PLATON (Spek, 1998) and SHELXL97.

ent-Kaur-16-ene-1,6,7,15-tetrol-7,20-epoxy-1-acetate top
Crystal data top
C22H32O6F(000) = 424
Mr = 392.48Dx = 1.313 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.9870 (16) ÅCell parameters from 3394 reflections
b = 6.0330 (8) Åθ = 1.9–27.5°
c = 15.429 (3) ŵ = 0.09 mm1
β = 103.989 (6)°T = 150 K
V = 992.4 (3) Å3Needle, colourless
Z = 20.15 × 0.05 × 0.02 mm
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
3394 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode2168 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 1.9°
φ and ω scans to fill Ewald sphereh = 1413
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 57
Tmin = 0.987, Tmax = 0.998l = 1818
7295 measured reflections
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)] = 0.059H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.0484P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
3394 reflectionsΔρmax = 0.21 e Å3
268 parametersΔρmin = 0.26 e Å3
1 restraintAbsolute structure: Flack (1983), 1054 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1.7 (16)
Special details top

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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
O10.1111 (2)1.0909 (4)0.25661 (15)0.0333 (6)
O20.0723 (2)0.7328 (5)0.08201 (18)0.0338 (7)
H20.097 (5)0.831 (10)0.052 (3)0.074 (19)*
O30.0583 (3)1.1301 (5)0.10578 (17)0.0356 (6)
H30.112 (3)1.249 (8)0.113 (2)0.043 (12)*
O40.1339 (3)0.5287 (4)0.06129 (16)0.0335 (6)
H40.057 (4)0.572 (8)0.057 (3)0.057 (14)*
O50.2501 (2)0.6552 (5)0.45729 (15)0.0362 (7)
O60.3354 (2)0.3276 (5)0.50887 (17)0.0461 (7)
C10.1542 (3)0.5484 (7)0.3864 (2)0.0316 (9)
H10.18690.40310.37050.034 (2)*
C20.0430 (3)0.5085 (7)0.4252 (2)0.0343 (9)
H2A0.02100.64790.45160.034 (2)*
H2B0.06530.39680.47340.034 (2)*
C30.0700 (3)0.4272 (7)0.3542 (3)0.0354 (9)
H3A0.13980.39530.38260.034 (2)*
H3B0.04790.28750.32810.034 (2)*
C40.1131 (3)0.5974 (7)0.2800 (2)0.0326 (9)
C50.0008 (3)0.6505 (6)0.2400 (2)0.0283 (8)
H50.01490.51260.20780.034 (2)*
C60.0260 (3)0.8312 (6)0.1686 (2)0.0291 (8)
H60.09290.93000.18090.034 (2)*
C70.0907 (3)0.9705 (6)0.1736 (2)0.0298 (9)
C80.2091 (3)0.8381 (7)0.1716 (2)0.0306 (9)
C90.2298 (3)0.6652 (6)0.2495 (2)0.0284 (8)
H90.21300.51540.22140.034 (2)*
C100.1306 (3)0.7037 (6)0.3048 (2)0.0293 (9)
C110.3674 (3)0.6655 (7)0.3041 (2)0.0346 (9)
H11A0.38200.79910.34250.034 (2)*
H11B0.38160.53410.34370.034 (2)*
C120.4632 (3)0.6625 (7)0.2461 (3)0.0415 (10)
H12A0.47370.50850.22690.034 (2)*
H12B0.54540.71450.28200.034 (2)*
C130.4206 (3)0.8128 (8)0.1623 (2)0.0405 (10)
H130.49370.88540.14580.034 (2)*
C140.3257 (3)0.9849 (7)0.1797 (3)0.0365 (9)
H14A0.35341.05120.23990.034 (2)*
H14B0.31081.10410.13420.034 (2)*
C150.2059 (4)0.7275 (7)0.0806 (3)0.0364 (10)
H150.17390.83730.03190.034 (2)*
C160.3427 (4)0.6803 (7)0.0852 (3)0.0399 (10)
C170.3851 (4)0.5429 (8)0.0328 (3)0.0569 (13)
H17A0.32780.46350.01270.034 (2)*
H17B0.47280.52340.04040.034 (2)*
C180.2165 (3)0.4924 (7)0.2065 (3)0.0388 (10)
H18A0.24500.59970.15810.063 (4)*
H18B0.28710.44980.23130.063 (4)*
H18C0.18320.36070.18300.063 (4)*
C190.1700 (3)0.8005 (7)0.3168 (2)0.0391 (10)
H19A0.19700.90970.26900.063 (4)*
H19B0.10670.86700.36570.063 (4)*
H19C0.24230.75350.33900.063 (4)*
C200.1412 (3)0.9457 (6)0.3338 (2)0.0326 (9)
H20A0.08300.97510.37250.034 (2)*
H20B0.22760.97620.36890.034 (2)*
C210.3326 (3)0.5256 (8)0.5142 (2)0.0379 (10)
C220.4189 (4)0.6643 (8)0.5830 (3)0.0502 (12)
H22A0.50330.66080.57240.063 (4)*
H22B0.42150.60540.64260.063 (4)*
H22C0.38830.81740.57900.063 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0458 (15)0.0243 (15)0.0276 (14)0.0004 (12)0.0045 (11)0.0015 (11)
O20.0390 (15)0.0308 (16)0.0278 (15)0.0034 (13)0.0007 (12)0.0009 (13)
O30.0453 (15)0.0249 (15)0.0327 (14)0.0025 (13)0.0017 (11)0.0061 (13)
O40.0350 (15)0.0281 (15)0.0361 (15)0.0027 (13)0.0062 (12)0.0013 (12)
O50.0396 (14)0.0337 (16)0.0306 (14)0.0012 (13)0.0005 (11)0.0024 (13)
O60.0523 (17)0.0378 (18)0.0436 (17)0.0069 (14)0.0027 (13)0.0076 (15)
C10.0364 (19)0.027 (2)0.028 (2)0.0019 (18)0.0023 (16)0.0049 (17)
C20.040 (2)0.033 (2)0.030 (2)0.0018 (18)0.0088 (16)0.0040 (18)
C30.038 (2)0.029 (2)0.041 (2)0.0001 (19)0.0133 (17)0.0011 (19)
C40.0308 (19)0.032 (2)0.035 (2)0.0002 (17)0.0082 (16)0.0002 (18)
C50.0316 (19)0.0244 (19)0.0261 (18)0.0009 (17)0.0018 (15)0.0002 (17)
C60.0297 (17)0.026 (2)0.029 (2)0.0022 (17)0.0019 (14)0.0007 (17)
C70.040 (2)0.021 (2)0.026 (2)0.0013 (17)0.0015 (16)0.0003 (16)
C80.0330 (19)0.026 (2)0.030 (2)0.0022 (17)0.0028 (15)0.0015 (18)
C90.0287 (18)0.0246 (19)0.031 (2)0.0006 (17)0.0052 (15)0.0028 (17)
C100.033 (2)0.030 (2)0.0231 (18)0.0020 (17)0.0029 (15)0.0035 (16)
C110.0298 (18)0.036 (2)0.035 (2)0.0025 (18)0.0017 (16)0.0008 (19)
C120.0326 (19)0.044 (3)0.044 (2)0.001 (2)0.0033 (17)0.000 (2)
C130.037 (2)0.045 (3)0.041 (2)0.009 (2)0.0120 (17)0.001 (2)
C140.042 (2)0.034 (2)0.034 (2)0.0068 (19)0.0102 (17)0.0000 (19)
C150.044 (2)0.030 (2)0.033 (2)0.0042 (18)0.0046 (17)0.0034 (18)
C160.039 (2)0.041 (3)0.042 (2)0.005 (2)0.0135 (18)0.001 (2)
C170.044 (2)0.069 (3)0.058 (3)0.006 (3)0.013 (2)0.022 (3)
C180.0314 (19)0.038 (3)0.046 (2)0.0070 (19)0.0071 (17)0.001 (2)
C190.038 (2)0.039 (2)0.041 (2)0.0056 (19)0.0092 (17)0.002 (2)
C200.0372 (19)0.028 (2)0.030 (2)0.0039 (18)0.0033 (16)0.0059 (18)
C210.036 (2)0.044 (3)0.035 (2)0.000 (2)0.0090 (17)0.009 (2)
C220.046 (2)0.055 (3)0.041 (2)0.007 (2)0.0072 (19)0.004 (2)
Geometric parameters (Å, º) top
O1—C71.442 (4)C9—C111.543 (4)
O1—C201.451 (4)C9—C101.556 (5)
O2—C61.438 (4)C9—H91.0000
O2—H20.76 (5)C10—C201.523 (5)
O3—C71.403 (4)C11—C121.537 (5)
O3—H30.92 (4)C11—H11A0.9900
O4—C151.428 (4)C11—H11B0.9900
O4—H40.87 (4)C12—C131.557 (6)
O5—C211.349 (5)C12—H12A0.9900
O5—C11.471 (4)C12—H12B0.9900
O6—C211.198 (5)C13—C161.515 (6)
C1—C21.504 (5)C13—C141.540 (6)
C1—C101.540 (5)C13—H131.0000
C1—H11.0000C14—H14A0.9900
C2—C31.524 (5)C14—H14B0.9900
C2—H2A0.9900C15—C161.515 (6)
C2—H2B0.9900C15—H151.0000
C3—C41.526 (5)C16—C171.319 (6)
C3—H3A0.9900C17—H17A0.9500
C3—H3B0.9900C17—H17B0.9500
C4—C181.535 (5)C18—H18A0.9800
C4—C191.544 (5)C18—H18B0.9800
C4—C51.557 (5)C18—H18C0.9800
C5—C61.527 (5)C19—H19A0.9800
C5—C101.564 (5)C19—H19B0.9800
C5—H51.0000C19—H19C0.9800
C6—C71.519 (5)C20—H20A0.9900
C6—H61.0000C20—H20B0.9900
C7—C81.533 (5)C21—C221.496 (6)
C8—C141.538 (5)C22—H22A0.9800
C8—C151.547 (5)C22—H22B0.9800
C8—C91.566 (5)C22—H22C0.9800
C7—O1—C20112.4 (3)C9—C10—C5105.7 (3)
C6—O2—H2104 (4)C12—C11—C9113.6 (3)
C7—O3—H3114 (2)C12—C11—H11A108.8
C15—O4—H4104 (3)C9—C11—H11A108.8
C21—O5—C1118.5 (3)C12—C11—H11B108.8
O5—C1—C2106.2 (3)C9—C11—H11B108.8
O5—C1—C10106.9 (3)H11A—C11—H11B107.7
C2—C1—C10115.4 (3)C11—C12—C13111.5 (3)
O5—C1—H1109.4C11—C12—H12A109.3
C2—C1—H1109.4C13—C12—H12A109.3
C10—C1—H1109.4C11—C12—H12B109.3
C1—C2—C3111.4 (3)C13—C12—H12B109.3
C1—C2—H2A109.3H12A—C12—H12B108.0
C3—C2—H2A109.3C16—C13—C14102.4 (3)
C1—C2—H2B109.3C16—C13—C12110.1 (4)
C3—C2—H2B109.3C14—C13—C12109.1 (3)
H2A—C2—H2B108.0C16—C13—H13111.6
C2—C3—C4111.9 (3)C14—C13—H13111.6
C2—C3—H3A109.2C12—C13—H13111.6
C4—C3—H3A109.2C8—C14—C13100.6 (3)
C2—C3—H3B109.2C8—C14—H14A111.7
C4—C3—H3B109.2C13—C14—H14A111.7
H3A—C3—H3B107.9C8—C14—H14B111.7
C3—C4—C18108.5 (3)C13—C14—H14B111.7
C3—C4—C19109.8 (3)H14A—C14—H14B109.4
C18—C4—C19107.9 (3)O4—C15—C16110.2 (3)
C3—C4—C5107.6 (3)O4—C15—C8116.2 (3)
C18—C4—C5108.3 (3)C16—C15—C8103.5 (3)
C19—C4—C5114.7 (3)O4—C15—H15108.9
C6—C5—C4113.6 (3)C16—C15—H15108.9
C6—C5—C10107.6 (3)C8—C15—H15108.9
C4—C5—C10119.0 (3)C17—C16—C15125.7 (4)
C6—C5—H5105.2C17—C16—C13126.6 (4)
C4—C5—H5105.2C15—C16—C13107.7 (3)
C10—C5—H5105.2C16—C17—H17A120.0
O2—C6—C7112.3 (3)C16—C17—H17B120.0
O2—C6—C5109.8 (3)H17A—C17—H17B120.0
C7—C6—C5110.2 (3)C4—C18—H18A109.5
O2—C6—H6108.1C4—C18—H18B109.5
C7—C6—H6108.1H18A—C18—H18B109.5
C5—C6—H6108.1C4—C18—H18C109.5
O3—C7—O1105.9 (3)H18A—C18—H18C109.5
O3—C7—C6106.5 (3)H18B—C18—H18C109.5
O1—C7—C6105.8 (3)C4—C19—H19A109.5
O3—C7—C8114.0 (3)C4—C19—H19B109.5
O1—C7—C8109.2 (3)H19A—C19—H19B109.5
C6—C7—C8114.9 (3)C4—C19—H19C109.5
C7—C8—C14113.1 (3)H19A—C19—H19C109.5
C7—C8—C15114.2 (3)H19B—C19—H19C109.5
C14—C8—C1599.1 (3)O1—C20—C10110.6 (3)
C7—C8—C9107.4 (3)O1—C20—H20A109.5
C14—C8—C9111.0 (3)C10—C20—H20A109.5
C15—C8—C9112.1 (3)O1—C20—H20B109.5
C11—C9—C10115.1 (3)C10—C20—H20B109.5
C11—C9—C8111.1 (3)H20A—C20—H20B108.1
C10—C9—C8109.3 (3)O6—C21—O5123.9 (4)
C11—C9—H9107.0O6—C21—C22125.7 (4)
C10—C9—H9107.0O5—C21—C22110.4 (4)
C8—C9—H9107.0C21—C22—H22A109.5
C20—C10—C1110.9 (3)C21—C22—H22B109.5
C20—C10—C9106.9 (3)H22A—C22—H22B109.5
C1—C10—C9110.8 (3)C21—C22—H22C109.5
C20—C10—C5112.2 (3)H22A—C22—H22C109.5
C1—C10—C5110.2 (3)H22B—C22—H22C109.5
C21—O5—C1—C289.9 (4)C2—C1—C10—C9158.6 (3)
C21—O5—C1—C10146.4 (3)O5—C1—C10—C5159.9 (3)
O5—C1—C2—C3172.1 (3)C2—C1—C10—C542.0 (4)
C10—C1—C2—C353.9 (5)C11—C9—C10—C2071.1 (4)
C1—C2—C3—C461.8 (4)C8—C9—C10—C2054.7 (4)
C2—C3—C4—C18173.4 (3)C11—C9—C10—C149.8 (4)
C2—C3—C4—C1968.9 (4)C8—C9—C10—C1175.6 (3)
C2—C3—C4—C556.5 (4)C11—C9—C10—C5169.2 (3)
C3—C4—C5—C6176.1 (3)C8—C9—C10—C565.0 (4)
C18—C4—C5—C666.8 (4)C6—C5—C10—C2047.3 (4)
C19—C4—C5—C653.7 (4)C4—C5—C10—C2083.6 (4)
C3—C4—C5—C1048.0 (4)C6—C5—C10—C1171.4 (3)
C18—C4—C5—C10165.1 (3)C4—C5—C10—C140.6 (5)
C19—C4—C5—C1074.5 (4)C6—C5—C10—C968.8 (4)
C4—C5—C6—O290.7 (4)C4—C5—C10—C9160.3 (3)
C10—C5—C6—O2135.5 (3)C10—C9—C11—C12171.2 (3)
C4—C5—C6—C7145.1 (3)C8—C9—C11—C1246.3 (4)
C10—C5—C6—C711.3 (4)C9—C11—C12—C1339.5 (5)
C20—O1—C7—O3177.8 (3)C11—C12—C13—C1690.0 (4)
C20—O1—C7—C665.1 (3)C11—C12—C13—C1421.7 (4)
C20—O1—C7—C859.0 (4)C7—C8—C14—C13172.3 (3)
O2—C6—C7—O356.8 (4)C15—C8—C14—C1351.1 (3)
C5—C6—C7—O3179.5 (3)C9—C8—C14—C1366.9 (4)
O2—C6—C7—O1169.1 (3)C16—C13—C14—C842.4 (4)
C5—C6—C7—O168.1 (4)C12—C13—C14—C874.3 (3)
O2—C6—C7—C870.4 (4)C7—C8—C15—O478.1 (4)
C5—C6—C7—C852.4 (4)C14—C8—C15—O4161.4 (3)
O3—C7—C8—C1458.6 (4)C9—C8—C15—O444.3 (4)
O1—C7—C8—C1459.6 (4)C7—C8—C15—C16161.0 (3)
C6—C7—C8—C14178.2 (3)C14—C8—C15—C1640.5 (4)
O3—C7—C8—C1553.7 (4)C9—C8—C15—C1676.7 (4)
O1—C7—C8—C15171.9 (3)O4—C15—C16—C1738.5 (6)
C6—C7—C8—C1569.5 (4)C8—C15—C16—C17163.4 (5)
O3—C7—C8—C9178.7 (3)O4—C15—C16—C13139.7 (3)
O1—C7—C8—C963.1 (4)C8—C15—C16—C1314.8 (4)
C6—C7—C8—C955.4 (4)C14—C13—C16—C17164.8 (5)
C7—C8—C9—C11132.9 (3)C12—C13—C16—C1779.2 (5)
C14—C8—C9—C118.8 (4)C14—C13—C16—C1517.0 (4)
C15—C8—C9—C11101.0 (4)C12—C13—C16—C1599.0 (4)
C7—C8—C9—C104.7 (4)C7—O1—C20—C105.3 (4)
C14—C8—C9—C10119.4 (3)C1—C10—C20—O1176.5 (3)
C15—C8—C9—C10130.9 (3)C9—C10—C20—O162.6 (3)
O5—C1—C10—C2035.0 (4)C5—C10—C20—O152.7 (4)
C2—C1—C10—C2082.9 (4)C1—O5—C21—O62.5 (6)
O5—C1—C10—C983.5 (3)C1—O5—C21—C22177.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O4i0.76 (6)2.07 (5)2.795 (4)158 (5)
O3—H3···O4ii0.92 (4)1.91 (5)2.687 (4)142 (3)
O4—H4···O20.87 (5)1.84 (5)2.665 (5)158 (4)
Symmetry codes: (i) x, y+1/2, z; (ii) x, y+1, z.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds