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The title compound, C20H30O2, also known as tagalsin F, is a diterpenoid which was isolated from Ceriops tagal (Perr.). One of the three fused cyclo­hexane rings adopts a half-chair conformation and the other two cyclo­hexane rings are in standard chair conformations. The hydroxy­methyl­idene substituent is attached to the half-chair cyclo­hexane. The mol­ecular structure is stabilized by intra­molecular O—H...O hydrogen bonds and weak inter­molecular C—H...O inter­actions. In the crystal structure, mol­ecules are arranged alternately in a head-to-tail and tail-to-head fashion along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046277/sj2157sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046277/sj2157Isup2.hkl
Contains datablock I

CCDC reference: 630474

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.106
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
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 30.00 From the CIF: _reflns_number_total 2881 Count of symmetry unique reflns 2883 Completeness (_total/calc) 99.93% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 6 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 0 ALERT type 5 Informative message, check

Computing details top

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).

7-Ethenyl-1-[(Z)-hydroxymethylidene]-4 b,7,10a-trimethylperhydrophenanthren-2-one top
Crystal data top
C20H30O2Dx = 1.164 Mg m3
Mr = 302.44Melting point = 374–375 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2631 reflections
a = 6.6826 (2) Åθ = 1.7–30.0°
b = 10.8100 (3) ŵ = 0.07 mm1
c = 23.8901 (6) ÅT = 100 K
V = 1725.79 (8) Å3Plate, colourless
Z = 40.45 × 0.22 × 0.05 mm
F(000) = 664
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
2881 independent reflections
Radiation source: fine-focus sealed tube2631 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 1.7°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1515
Tmin = 0.968, Tmax = 0.996l = 3330
26531 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0546P)2 + 0.4474P]
where P = (Fo2 + 2Fc2)/3
2881 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.18 e Å3
Special details top

Experimental. The low-temparture data were collected with the Oxford Cyrosystem 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.9686 (2)0.65093 (13)0.50805 (5)0.0269 (3)
H1A1.00370.58110.51730.040*
O20.9753 (2)0.42367 (12)0.50810 (5)0.0235 (3)
C10.7583 (2)0.53308 (15)0.44803 (6)0.0155 (3)
C20.8425 (2)0.42193 (16)0.46955 (7)0.0173 (3)
C30.7848 (3)0.29708 (16)0.44753 (8)0.0234 (4)
H3A0.73240.24890.47850.028*
H3B0.90550.25610.43460.028*
C40.6309 (3)0.29322 (16)0.39984 (7)0.0220 (4)
H4A0.50240.27000.41550.026*
H4B0.66990.22850.37390.026*
C50.6032 (2)0.41444 (15)0.36639 (7)0.0164 (3)
H5A0.47180.40650.34860.020*
C60.5814 (2)0.52544 (16)0.40765 (6)0.0164 (3)
C70.5487 (3)0.64520 (16)0.37398 (7)0.0204 (3)
H7A0.41730.64240.35680.024*
H7B0.55080.71490.39950.024*
C80.7049 (3)0.66620 (15)0.32852 (7)0.0196 (3)
H8A0.83640.67390.34540.024*
H8B0.67570.74230.30860.024*
C90.7032 (3)0.55734 (14)0.28761 (6)0.0156 (3)
H9A0.56540.55000.27390.019*
C100.7531 (2)0.43318 (14)0.31696 (6)0.0146 (3)
C110.7199 (3)0.33122 (15)0.27275 (7)0.0192 (3)
H11A0.75160.25160.28920.023*
H11B0.57970.33010.26220.023*
C120.8469 (3)0.34907 (15)0.22014 (7)0.0197 (3)
H12A0.81200.28510.19340.024*
H12B0.98650.33770.23000.024*
C130.8234 (3)0.47663 (16)0.19143 (6)0.0180 (3)
C140.8341 (3)0.58054 (15)0.23615 (6)0.0182 (3)
H14A0.97200.58960.24820.022*
H14B0.79370.65800.21900.022*
C151.0007 (3)0.49159 (17)0.15239 (8)0.0254 (4)
H15A1.12530.49620.16960.030*
C161.0017 (4)0.4989 (2)0.09763 (8)0.0363 (5)
H16A0.88210.49500.07780.044*
H16B1.12220.50810.07860.044*
C170.6233 (3)0.48279 (18)0.16003 (7)0.0246 (4)
H17A0.61730.41720.13300.037*
H17B0.61230.56100.14130.037*
H17C0.51520.47400.18620.037*
C180.8300 (3)0.64333 (16)0.46938 (7)0.0209 (3)
H18A0.77660.71660.45550.025*
C190.3931 (3)0.5072 (2)0.44407 (7)0.0252 (4)
H19A0.36820.58100.46530.038*
H19B0.41360.43900.46910.038*
H19C0.28020.49030.42040.038*
C200.9731 (2)0.42912 (16)0.33655 (7)0.0189 (3)
H20A1.05970.44400.30520.028*
H20B1.00170.34920.35210.028*
H20C0.99460.49160.36450.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0246 (6)0.0290 (6)0.0272 (6)0.0022 (6)0.0059 (6)0.0083 (5)
O20.0216 (6)0.0299 (6)0.0191 (5)0.0030 (6)0.0066 (5)0.0020 (5)
C10.0137 (7)0.0188 (7)0.0142 (6)0.0005 (6)0.0001 (5)0.0004 (6)
C20.0159 (7)0.0220 (7)0.0141 (7)0.0001 (7)0.0013 (6)0.0016 (6)
C30.0309 (9)0.0187 (7)0.0207 (8)0.0012 (8)0.0033 (7)0.0051 (6)
C40.0285 (9)0.0190 (7)0.0185 (8)0.0077 (7)0.0020 (7)0.0031 (6)
C50.0144 (7)0.0185 (7)0.0162 (7)0.0035 (6)0.0021 (6)0.0003 (6)
C60.0132 (6)0.0220 (8)0.0140 (7)0.0015 (6)0.0008 (5)0.0011 (6)
C70.0232 (8)0.0223 (8)0.0157 (7)0.0085 (7)0.0004 (6)0.0009 (6)
C80.0277 (9)0.0148 (7)0.0163 (7)0.0021 (7)0.0003 (6)0.0000 (6)
C90.0180 (7)0.0150 (7)0.0140 (7)0.0014 (6)0.0010 (6)0.0002 (5)
C100.0147 (7)0.0145 (6)0.0146 (6)0.0013 (6)0.0009 (6)0.0007 (5)
C110.0257 (8)0.0151 (7)0.0168 (7)0.0023 (7)0.0034 (6)0.0014 (6)
C120.0249 (8)0.0174 (7)0.0167 (7)0.0019 (7)0.0015 (6)0.0032 (6)
C130.0223 (8)0.0194 (7)0.0124 (7)0.0019 (7)0.0011 (6)0.0009 (6)
C140.0234 (7)0.0164 (7)0.0150 (7)0.0023 (7)0.0003 (6)0.0008 (6)
C150.0275 (9)0.0257 (9)0.0230 (8)0.0017 (8)0.0028 (7)0.0020 (7)
C160.0453 (12)0.0407 (11)0.0228 (9)0.0060 (11)0.0074 (9)0.0001 (8)
C170.0290 (9)0.0262 (9)0.0187 (8)0.0014 (8)0.0079 (7)0.0005 (7)
C180.0208 (8)0.0206 (8)0.0214 (8)0.0028 (7)0.0001 (7)0.0036 (6)
C190.0145 (7)0.0436 (11)0.0176 (7)0.0013 (8)0.0012 (6)0.0006 (7)
C200.0155 (7)0.0241 (8)0.0171 (7)0.0025 (7)0.0015 (6)0.0006 (6)
Geometric parameters (Å, º) top
O1—C181.311 (2)C10—C111.542 (2)
O1—H1A0.8200C10—C201.543 (2)
O2—C21.2790 (19)C11—C121.529 (2)
C1—C181.382 (2)C11—H11A0.9700
C1—C21.423 (2)C11—H11B0.9700
C1—C61.528 (2)C12—C131.548 (2)
C2—C31.499 (2)C12—H12A0.9700
C3—C41.536 (3)C12—H12B0.9700
C3—H3A0.9700C13—C151.516 (2)
C3—H3B0.9700C13—C171.534 (2)
C4—C51.546 (2)C13—C141.552 (2)
C4—H4A0.9700C14—H14A0.9700
C4—H4B0.9700C14—H14B0.9700
C5—C61.560 (2)C15—C161.311 (3)
C5—C101.561 (2)C15—H15A0.9300
C5—H5A0.9800C16—H16A0.9300
C6—C71.540 (2)C16—H16B0.9300
C6—C191.543 (2)C17—H17A0.9600
C7—C81.523 (2)C17—H17B0.9600
C7—H7A0.9700C17—H17C0.9600
C7—H7B0.9700C18—H18A0.9300
C8—C91.530 (2)C19—H19A0.9600
C8—H8A0.9700C19—H19B0.9600
C8—H8B0.9700C19—H19C0.9600
C9—C141.530 (2)C20—H20A0.9600
C9—C101.551 (2)C20—H20B0.9600
C9—H9A0.9800C20—H20C0.9600
C18—O1—H1A109.5C20—C10—C5112.20 (12)
C18—C1—C2117.22 (15)C9—C10—C5108.44 (13)
C18—C1—C6123.22 (15)C12—C11—C10113.14 (14)
C2—C1—C6119.26 (14)C12—C11—H11A108.9
O2—C2—C1121.49 (15)C10—C11—H11A108.9
O2—C2—C3116.39 (15)C12—C11—H11B108.9
C1—C2—C3122.10 (14)C10—C11—H11B109.0
C2—C3—C4117.21 (14)H11A—C11—H11B107.8
C2—C3—H3A108.0C11—C12—C13114.86 (14)
C4—C3—H3A108.0C11—C12—H12A108.6
C2—C3—H3B108.0C13—C12—H12A108.6
C4—C3—H3B108.0C11—C12—H12B108.6
H3A—C3—H3B107.2C13—C12—H12B108.6
C3—C4—C5116.14 (14)H12A—C12—H12B107.5
C3—C4—H4A108.3C15—C13—C17112.06 (13)
C5—C4—H4A108.3C15—C13—C12106.75 (14)
C3—C4—H4B108.3C17—C13—C12110.11 (14)
C5—C4—H4B108.3C15—C13—C14108.06 (14)
H4A—C4—H4B107.4C17—C13—C14110.20 (14)
C4—C5—C6109.66 (12)C12—C13—C14109.57 (12)
C4—C5—C10115.11 (14)C9—C14—C13114.09 (13)
C6—C5—C10115.99 (13)C9—C14—H14A108.7
C4—C5—H5A104.9C13—C14—H14A108.7
C6—C5—H5A104.9C9—C14—H14B108.7
C10—C5—H5A104.9C13—C14—H14B108.7
C1—C6—C7113.20 (14)H14A—C14—H14B107.6
C1—C6—C19106.37 (12)C16—C15—C13128.7 (2)
C7—C6—C19106.66 (14)C16—C15—H15A115.7
C1—C6—C5111.60 (13)C13—C15—H15A115.7
C7—C6—C5109.26 (12)C15—C16—H16A120.0
C19—C6—C5109.55 (14)C15—C16—H16B120.0
C8—C7—C6113.62 (14)H16A—C16—H16B120.0
C8—C7—H7A108.8C13—C17—H17A109.5
C6—C7—H7A108.8C13—C17—H17B109.5
C8—C7—H7B108.8H17A—C17—H17B109.5
C6—C7—H7B108.8C13—C17—H17C109.5
H7A—C7—H7B107.7H17A—C17—H17C109.5
C7—C8—C9109.62 (14)H17B—C17—H17C109.5
C7—C8—H8A109.7O1—C18—C1124.00 (16)
C9—C8—H8A109.7O1—C18—H18A118.0
C7—C8—H8B109.7C1—C18—H18A118.0
C9—C8—H8B109.7C6—C19—H19A109.5
H8A—C8—H8B108.2C6—C19—H19B109.5
C8—C9—C14112.52 (13)H19A—C19—H19B109.5
C8—C9—C10112.03 (12)C6—C19—H19C109.5
C14—C9—C10112.47 (13)H19A—C19—H19C109.5
C8—C9—H9A106.4H19B—C19—H19C109.5
C14—C9—H9A106.4C10—C20—H20A109.5
C10—C9—H9A106.4C10—C20—H20B109.5
C11—C10—C20108.91 (14)H20A—C20—H20B109.5
C11—C10—C9106.14 (12)C10—C20—H20C109.5
C20—C10—C9111.51 (14)H20A—C20—H20C109.5
C11—C10—C5109.45 (13)H20B—C20—H20C109.5
C18—C1—C2—O21.8 (2)C14—C9—C10—C1159.00 (17)
C6—C1—C2—O2172.06 (14)C8—C9—C10—C2068.45 (17)
C18—C1—C2—C3176.69 (17)C14—C9—C10—C2059.47 (16)
C6—C1—C2—C39.5 (2)C8—C9—C10—C555.57 (17)
O2—C2—C3—C4177.97 (15)C14—C9—C10—C5176.51 (12)
C1—C2—C3—C40.6 (3)C4—C5—C10—C1163.89 (17)
C2—C3—C4—C519.5 (2)C6—C5—C10—C11166.18 (13)
C3—C4—C5—C647.1 (2)C4—C5—C10—C2057.13 (18)
C3—C4—C5—C1085.83 (18)C6—C5—C10—C2072.80 (18)
C18—C1—C6—C724.6 (2)C4—C5—C10—C9179.25 (13)
C2—C1—C6—C7161.90 (14)C6—C5—C10—C950.81 (17)
C18—C1—C6—C1992.17 (19)C20—C10—C11—C1262.39 (17)
C2—C1—C6—C1981.29 (19)C9—C10—C11—C1257.79 (18)
C18—C1—C6—C5148.40 (16)C5—C10—C11—C12174.62 (14)
C2—C1—C6—C538.1 (2)C10—C11—C12—C1354.57 (19)
C4—C5—C6—C155.43 (18)C11—C12—C13—C15163.17 (14)
C10—C5—C6—C177.07 (17)C11—C12—C13—C1774.98 (17)
C4—C5—C6—C7178.61 (14)C11—C12—C13—C1446.38 (19)
C10—C5—C6—C748.90 (18)C8—C9—C14—C13175.48 (14)
C4—C5—C6—C1962.11 (17)C10—C9—C14—C1356.86 (18)
C10—C5—C6—C19165.40 (13)C15—C13—C14—C9163.49 (14)
C1—C6—C7—C873.02 (17)C17—C13—C14—C973.76 (17)
C19—C6—C7—C8170.34 (14)C12—C13—C14—C947.54 (19)
C5—C6—C7—C852.01 (18)C17—C13—C15—C165.6 (3)
C6—C7—C8—C958.85 (18)C12—C13—C15—C16115.0 (2)
C7—C8—C9—C14171.61 (14)C14—C13—C15—C16127.2 (2)
C7—C8—C9—C1060.50 (18)C2—C1—C18—O10.4 (2)
C8—C9—C10—C11173.08 (14)C6—C1—C18—O1173.20 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.821.732.4571 (19)147
C3—H3A···O2i0.972.563.331 (2)137
Symmetry code: (i) x1/2, y+1/2, z+1.
 

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