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In the crystal structure of the title compound, C21H34O3, mol­ecules are linked to each other by intermolecular O—H...O hydrogen bonds, involving the ester carbonyl group and the hydroxyl group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009554/wn6340sup1.cif
Contains datablocks 2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009554/wn63402sup2.hkl
Contains datablock 2

CCDC reference: 274659

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.032
  • wR factor = 0.090
  • Data-to-parameter ratio = 6.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 60.02 Deg.
Author Response: Data were collected using Cu K\a radiation. Angles higher than 60 (120 for 2\q) are limited by experimental conditions.

Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5618 PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 60.02 Deg.
Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5618 Proportion of unique data used 1.0000 Ratio reflections to parameters 6.8394 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.84 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.06 Ratio
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 60.02 From the CIF: _reflns_number_total 1491 Count of symmetry unique reflns 1498 Completeness (_total/calc) 99.53% 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
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 6 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CRYSOM (Martinez-Ripoll & Cano, 1996); cell refinement: CRYSOM; data reduction: X-RAY80 (Stewart et al., 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Methyl ent-15β-hydroxy-16α-kauran-19-oate top
Crystal data top
C21H34O3F(000) = 368
Mr = 334.48Dx = 1.184 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
a = 7.3470 (15) ÅCell parameters from 20 reflections
b = 9.5010 (19) Åθ = 8–20°
c = 13.568 (3) ŵ = 0.60 mm1
β = 97.81 (3)°T = 293 K
V = 938.3 (3) Å3Prism, colorless
Z = 20.2 × 0.2 × 0.2 mm
Data collection top
Seifert XRD 3003 SC
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 60.0°, θmin = 3.3°
Graphite monochromatorh = 08
ω/2θ scansk = 010
1491 measured reflectionsl = 1414
1491 independent reflections2 standard reflections every 700 reflections
1434 reflections with I > 2σ(I) intensity decay: 1%
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)] = 0.032H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0696P)2 + 0.0837P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.004
1491 reflectionsΔρmax = 0.16 e Å3
218 parametersΔρmin = 0.13 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.042 (3)
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
xyzUiso*/Ueq
O10.7436 (3)0.0187 (2)0.88082 (15)0.0570 (6)
O20.8933 (2)0.1770 (2)0.80173 (13)0.0472 (5)
O30.5794 (3)0.8800 (2)0.70158 (16)0.0625 (6)
H3A0.60320.89830.76100.094*
C10.3238 (3)0.3209 (3)0.85592 (19)0.0381 (6)
H1A0.29830.39590.90060.046*
H1B0.21030.29990.81310.046*
C20.3832 (3)0.1911 (3)0.91720 (19)0.0457 (7)
H2A0.39520.11220.87320.055*
H2B0.29030.16750.95890.055*
C30.5659 (4)0.2171 (3)0.98216 (19)0.0464 (7)
H3B0.60380.13111.01760.056*
H3C0.54830.28831.03120.056*
C40.7193 (3)0.2648 (3)0.92445 (16)0.0346 (5)
C50.6506 (3)0.3962 (2)0.86144 (15)0.0288 (5)
H5A0.61770.46320.91110.035*
C100.4666 (3)0.3743 (2)0.79075 (16)0.0283 (5)
C60.7907 (3)0.4768 (3)0.80959 (18)0.0334 (5)
H6A0.90540.48460.85400.040*
H6B0.81430.42570.75070.040*
C70.7186 (3)0.6231 (3)0.78013 (18)0.0363 (6)
H7A0.81120.67410.75000.044*
H7B0.69640.67390.83930.044*
C80.5417 (3)0.6176 (2)0.70735 (17)0.0304 (5)
C90.3993 (3)0.5210 (3)0.74873 (16)0.0291 (5)
H9A0.36610.57190.80650.035*
C140.5721 (3)0.5749 (3)0.60200 (16)0.0378 (6)
H14A0.67450.62550.58060.045*
H14B0.59350.47450.59750.045*
C130.3899 (4)0.6176 (3)0.54113 (17)0.0432 (6)
H13A0.39980.61650.46980.052*
C120.2405 (4)0.5170 (3)0.56482 (19)0.0485 (7)
H12A0.12470.54390.52630.058*
H12B0.27000.42270.54480.058*
C110.2182 (3)0.5159 (3)0.67451 (17)0.0409 (6)
H11A0.15150.43150.68790.049*
H11B0.14320.59590.68770.049*
C160.3693 (4)0.7689 (3)0.57790 (19)0.0464 (7)
H16A0.45300.82640.54440.056*
C150.4515 (4)0.7658 (3)0.6884 (2)0.0405 (6)
H15A0.35460.77910.73050.049*
C170.1810 (4)0.8373 (4)0.5545 (3)0.0712 (10)
H17A0.14210.83410.48400.107*
H17B0.18790.93340.57630.107*
H17C0.09410.78730.58830.107*
C180.8874 (4)0.3042 (3)1.00111 (19)0.0496 (7)
H18A0.92880.22261.03940.074*
H18B0.85300.37621.04460.074*
H18C0.98450.33830.96680.074*
C190.7812 (3)0.1400 (3)0.86704 (18)0.0374 (6)
C210.9613 (4)0.0660 (4)0.7438 (2)0.0589 (8)
H21C1.05200.10350.70630.088*
H21D0.86140.02730.69900.088*
H21A1.01560.00650.78750.088*
C200.4845 (3)0.2648 (3)0.70933 (18)0.0362 (5)
H20D0.52650.17730.73960.054*
H20A0.57120.29760.66760.054*
H20B0.36700.25120.66990.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0812 (14)0.0292 (11)0.0603 (12)0.0015 (10)0.0092 (10)0.0054 (9)
O20.0417 (9)0.0374 (10)0.0645 (11)0.0007 (8)0.0144 (8)0.0112 (9)
O30.0880 (15)0.0247 (10)0.0703 (13)0.0148 (10)0.0056 (11)0.0060 (9)
C10.0329 (12)0.0383 (14)0.0439 (13)0.0036 (10)0.0078 (10)0.0088 (11)
C20.0441 (13)0.0422 (15)0.0522 (15)0.0053 (12)0.0111 (12)0.0173 (13)
C30.0528 (15)0.0473 (17)0.0391 (13)0.0016 (13)0.0065 (11)0.0147 (12)
C40.0386 (12)0.0313 (13)0.0322 (12)0.0006 (10)0.0011 (10)0.0019 (10)
C50.0303 (11)0.0262 (12)0.0293 (11)0.0025 (9)0.0017 (9)0.0036 (9)
C100.0278 (10)0.0258 (11)0.0311 (11)0.0047 (10)0.0033 (9)0.0003 (10)
C60.0281 (10)0.0332 (13)0.0380 (12)0.0049 (10)0.0018 (9)0.0013 (10)
C70.0366 (12)0.0306 (13)0.0409 (12)0.0092 (11)0.0025 (10)0.0002 (11)
C80.0368 (11)0.0224 (12)0.0313 (11)0.0042 (10)0.0025 (9)0.0018 (9)
C90.0302 (11)0.0282 (12)0.0290 (11)0.0005 (10)0.0039 (9)0.0018 (10)
C140.0425 (13)0.0359 (13)0.0363 (12)0.0042 (11)0.0105 (10)0.0034 (11)
C130.0528 (14)0.0468 (16)0.0290 (11)0.0031 (13)0.0014 (10)0.0071 (11)
C120.0480 (14)0.0517 (17)0.0416 (14)0.0081 (13)0.0096 (11)0.0059 (13)
C110.0310 (12)0.0422 (14)0.0481 (13)0.0031 (11)0.0005 (10)0.0096 (12)
C160.0499 (14)0.0415 (15)0.0474 (15)0.0017 (13)0.0048 (12)0.0151 (13)
C150.0490 (13)0.0250 (13)0.0479 (14)0.0011 (11)0.0088 (11)0.0026 (11)
C170.064 (2)0.066 (2)0.080 (2)0.0172 (17)0.0008 (17)0.0288 (19)
C180.0513 (15)0.0506 (17)0.0420 (14)0.0013 (13)0.0119 (12)0.0001 (13)
C190.0376 (12)0.0324 (16)0.0400 (12)0.0008 (11)0.0025 (10)0.0024 (11)
C210.0536 (16)0.0510 (18)0.0738 (19)0.0024 (14)0.0140 (14)0.0231 (16)
C200.0415 (12)0.0264 (12)0.0384 (12)0.0043 (10)0.0023 (10)0.0038 (11)
Geometric parameters (Å, º) top
O1—C191.205 (3)C8—C151.562 (3)
O2—C191.337 (3)C9—C111.556 (3)
O2—C211.445 (3)C9—H9A0.9800
O3—C151.430 (3)C14—C131.529 (3)
O3—H3A0.8200C14—H14A0.9700
C1—C21.518 (4)C14—H14B0.9700
C1—C101.547 (3)C13—C121.522 (4)
C1—H1A0.9700C13—C161.536 (4)
C1—H1B0.9700C13—H13A0.9800
C2—C31.523 (4)C12—C111.519 (4)
C2—H2A0.9700C12—H12A0.9700
C2—H2B0.9700C12—H12B0.9700
C3—C41.526 (3)C11—H11A0.9700
C3—H3B0.9700C11—H11B0.9700
C3—H3C0.9700C16—C171.522 (4)
C4—C191.522 (4)C16—C151.539 (4)
C4—C181.549 (3)C16—H16A0.9800
C4—C51.558 (3)C15—H15A0.9800
C5—C61.529 (3)C17—H17A0.9600
C5—C101.561 (3)C17—H17B0.9600
C5—H5A0.9800C17—H17C0.9600
C10—C201.536 (3)C18—H18A0.9600
C10—C91.560 (3)C18—H18B0.9600
C6—C71.521 (4)C18—H18C0.9600
C6—H6A0.9700C21—H21C0.9600
C6—H6B0.9700C21—H21D0.9600
C7—C81.523 (3)C21—H21A0.9600
C7—H7A0.9700C20—H20D0.9600
C7—H7B0.9700C20—H20A0.9600
C8—C141.531 (3)C20—H20B0.9600
C8—C91.554 (3)
C19—O2—C21117.3 (2)C13—C14—H14A111.4
C15—O3—H3A109.5C8—C14—H14A111.4
C2—C1—C10114.4 (2)C13—C14—H14B111.4
C2—C1—H1A108.7C8—C14—H14B111.4
C10—C1—H1A108.7H14A—C14—H14B109.3
C2—C1—H1B108.7C12—C13—C14108.8 (2)
C10—C1—H1B108.7C12—C13—C16114.4 (2)
H1A—C1—H1B107.6C14—C13—C16101.0 (2)
C1—C2—C3110.5 (2)C12—C13—H13A110.7
C1—C2—H2A109.6C14—C13—H13A110.7
C3—C2—H2A109.6C16—C13—H13A110.7
C1—C2—H2B109.6C11—C12—C13112.8 (2)
C3—C2—H2B109.6C11—C12—H12A109.0
H2A—C2—H2B108.1C13—C12—H12A109.0
C2—C3—C4113.9 (2)C11—C12—H12B109.0
C2—C3—H3B108.8C13—C12—H12B109.0
C4—C3—H3B108.8H12A—C12—H12B107.8
C2—C3—H3C108.8C12—C11—C9115.9 (2)
C4—C3—H3C108.8C12—C11—H11A108.3
H3B—C3—H3C107.7C9—C11—H11A108.3
C19—C4—C3108.9 (2)C12—C11—H11B108.3
C19—C4—C18105.4 (2)C9—C11—H11B108.3
C3—C4—C18107.7 (2)H11A—C11—H11B107.4
C19—C4—C5116.15 (18)C17—C16—C13117.3 (3)
C3—C4—C5108.21 (19)C17—C16—C15115.9 (3)
C18—C4—C5110.1 (2)C13—C16—C15104.8 (2)
C6—C5—C4117.76 (18)C17—C16—H16A106.0
C6—C5—C10111.39 (17)C13—C16—H16A106.0
C4—C5—C10114.79 (18)C15—C16—H16A106.0
C6—C5—H5A103.6O3—C15—C16105.8 (2)
C4—C5—H5A103.6O3—C15—C8113.9 (2)
C10—C5—H5A103.6C16—C15—C8106.2 (2)
C20—C10—C1108.7 (2)O3—C15—H15A110.2
C20—C10—C9113.32 (17)C16—C15—H15A110.2
C1—C10—C9107.21 (17)C8—C15—H15A110.2
C20—C10—C5112.36 (18)C16—C17—H17A109.5
C1—C10—C5106.87 (17)C16—C17—H17B109.5
C9—C10—C5108.10 (17)H17A—C17—H17B109.5
C7—C6—C5110.27 (19)C16—C17—H17C109.5
C7—C6—H6A109.6H17A—C17—H17C109.5
C5—C6—H6A109.6H17B—C17—H17C109.5
C7—C6—H6B109.6C4—C18—H18A109.5
C5—C6—H6B109.6C4—C18—H18B109.5
H6A—C6—H6B108.1H18A—C18—H18B109.5
C6—C7—C8112.05 (19)C4—C18—H18C109.5
C6—C7—H7A109.2H18A—C18—H18C109.5
C8—C7—H7A109.2H18B—C18—H18C109.5
C6—C7—H7B109.2O1—C19—O2122.0 (2)
C8—C7—H7B109.2O1—C19—C4125.1 (2)
H7A—C7—H7B107.9O2—C19—C4112.8 (2)
C7—C8—C14113.22 (19)O2—C21—H21C109.5
C7—C8—C9110.07 (17)O2—C21—H21D109.5
C14—C8—C9111.80 (19)H21C—C21—H21D109.5
C7—C8—C15112.45 (19)O2—C21—H21A109.5
C14—C8—C15101.4 (2)H21C—C21—H21A109.5
C9—C8—C15107.51 (19)H21D—C21—H21A109.5
C8—C9—C11110.05 (18)C10—C20—H20D109.5
C8—C9—C10117.67 (17)C10—C20—H20A109.5
C11—C9—C10114.2 (2)H20D—C20—H20A109.5
C8—C9—H9A104.5C10—C20—H20B109.5
C11—C9—H9A104.5H20D—C20—H20B109.5
C10—C9—H9A104.5H20A—C20—H20B109.5
C13—C14—C8101.88 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O1i0.822.142.883 (3)152
C1—H1B···O2ii0.972.593.432 (3)145
C21—H21D···O3iii0.962.503.300 (4)140
Symmetry codes: (i) x, y+1, z; (ii) x1, y, z; (iii) x, y1, z.
 

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