As part of our studies on synthetic derivatives of 6α,7β-dihydroxyvouacapan-17β-oic acid, isolated from the seeds of Pterodon polygalaeflorus Benth, the structure of the title compound, C
20H
29FO
3, was determined. The crystal packing is stabilized by C—H
O and C—H
F intermolecular interactions.
Supporting information
CCDC reference: 227886
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.043
- wR factor = 0.107
- Data-to-parameter ratio = 9.5
checkCIF/PLATON results
No syntax errors found
Alert level C
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 26.29
From the CIF: _reflns_number_total 2093
Count of symmetry unique reflns 2096
Completeness (_total/calc) 99.86%
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
1 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
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
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
Crystal data top
C20H29FO3 | F(000) = 728 |
Mr = 336.43 | Dx = 1.269 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 6.0284 (4) Å | θ = 10.3–18.3° |
b = 10.850 (2) Å | µ = 0.09 mm−1 |
c = 26.921 (3) Å | T = 293 K |
V = 1760.8 (4) Å3 | Prism, colourless |
Z = 4 | 0.02 × 0.01 × 0.01 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | θmax = 26.3°, θmin = 2.4° |
non–profiled ω/2θ scans | h = −7→0 |
2095 measured reflections | k = −13→0 |
2093 independent reflections | l = 0→33 |
1125 reflections with I > 2σ(I) | 3 standard reflections every 120 min |
Rint = 0.046 | intensity decay: 2% |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.044P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.107 | (Δ/σ)max = 0.004 |
S = 1.00 | Δρmax = 0.17 e Å−3 |
2093 reflections | Δρmin = −0.21 e Å−3 |
220 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F | 0.4431 (4) | 0.0249 (2) | 0.17975 (8) | 0.0567 (7) | |
O1 | 0.3507 (5) | 0.4461 (3) | 0.11689 (10) | 0.0600 (8) | |
O2 | 0.1207 (6) | 0.2461 (3) | 0.27601 (10) | 0.0806 (11) | |
O3 | 0.1926 (5) | 0.0687 (2) | 0.24009 (8) | 0.0525 (8) | |
C1 | 0.0958 (7) | 0.0882 (3) | 0.01635 (11) | 0.0447 (11) | |
H1A | 0.0203 | 0.1473 | −0.0048 | 0.054* | |
H1B | 0.2529 | 0.1077 | 0.0161 | 0.054* | |
C2 | 0.0610 (8) | −0.0418 (4) | −0.00427 (13) | 0.0539 (12) | |
H2A | −0.0967 | −0.0571 | −0.008 | 0.065* | |
H2B | 0.1286 | −0.0474 | −0.0369 | 0.065* | |
C3 | 0.1606 (8) | −0.1393 (3) | 0.02936 (13) | 0.0525 (12) | |
H3A | 0.3207 | −0.1304 | 0.0287 | 0.063* | |
H3B | 0.1258 | −0.2196 | 0.0156 | 0.063* | |
C4 | 0.0846 (7) | −0.1375 (3) | 0.08392 (13) | 0.0397 (10) | |
C5 | 0.1143 (6) | −0.0039 (3) | 0.10140 (11) | 0.0320 (9) | |
H5 | 0.2739 | 0.0108 | 0.098 | 0.038* | |
C6 | 0.0629 (6) | 0.0354 (3) | 0.15562 (12) | 0.0366 (9) | |
H6 | −0.0815 | 0.0009 | 0.1649 | 0.044* | |
C8 | 0.0389 (6) | 0.1763 (3) | 0.15234 (11) | 0.0337 (9) | |
H8 | −0.1162 | 0.1978 | 0.159 | 0.04* | |
C9 | 0.0928 (7) | 0.2116 (3) | 0.09863 (11) | 0.0343 (9) | |
H9 | 0.2548 | 0.2116 | 0.0956 | 0.041* | |
C10 | 0.0070 (6) | 0.0991 (3) | 0.06947 (11) | 0.0338 (9) | |
C11 | 0.0158 (7) | 0.3436 (3) | 0.09017 (13) | 0.0461 (11) | |
H11A | −0.1446 | 0.3477 | 0.0926 | 0.055* | |
H11B | 0.0586 | 0.3704 | 0.0571 | 0.055* | |
C12 | 0.1204 (8) | 0.4286 (4) | 0.12910 (14) | 0.0484 (11) | |
H12 | 0.0457 | 0.5088 | 0.1277 | 0.058* | |
C13 | 0.1280 (8) | 0.3862 (4) | 0.18337 (12) | 0.0477 (11) | |
H13 | −0.014 | 0.4031 | 0.1998 | 0.057* | |
C14 | 0.1850 (7) | 0.2497 (3) | 0.18726 (12) | 0.0366 (9) | |
H14 | 0.3391 | 0.2392 | 0.1764 | 0.044* | |
C15 | 0.4668 (8) | 0.4815 (4) | 0.16016 (16) | 0.0634 (12) | |
H15A | 0.5192 | 0.5656 | 0.157 | 0.076* | |
H15B | 0.5939 | 0.4281 | 0.1652 | 0.076* | |
C16 | 0.3080 (8) | 0.4709 (4) | 0.20380 (15) | 0.0629 (13) | |
H16A | 0.248 | 0.5507 | 0.2129 | 0.075* | |
H16B | 0.3803 | 0.4346 | 0.2325 | 0.075* | |
C17 | 0.1641 (8) | 0.1953 (4) | 0.23823 (15) | 0.0517 (11) | |
C18 | 0.2364 (8) | −0.2231 (4) | 0.11365 (16) | 0.0547 (12) | |
H18A | 0.177 | −0.234 | 0.1464 | 0.082* | |
H18B | 0.3817 | −0.1874 | 0.1159 | 0.082* | |
H18C | 0.2456 | −0.3016 | 0.0973 | 0.082* | |
C19 | −0.1523 (8) | −0.1876 (4) | 0.08895 (15) | 0.0558 (12) | |
H19A | −0.2478 | −0.1456 | 0.066 | 0.084* | |
H19B | −0.2043 | −0.1743 | 0.1222 | 0.084* | |
H19C | −0.1529 | −0.2743 | 0.0818 | 0.084* | |
C20 | −0.2486 (6) | 0.1014 (4) | 0.06859 (14) | 0.0502 (11) | |
H20A | −0.3045 | 0.0765 | 0.1004 | 0.075* | |
H20B | −0.3015 | 0.0457 | 0.0435 | 0.075* | |
H20C | −0.2989 | 0.1833 | 0.0613 | 0.075* | |
C21 | 0.2282 (7) | 0.0012 (4) | 0.19552 (13) | 0.0470 (11) | |
H21 | 0.214 | −0.087 | 0.2027 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F | 0.0483 (15) | 0.0724 (16) | 0.0494 (13) | 0.0063 (14) | −0.0093 (12) | 0.0025 (12) |
O1 | 0.064 (2) | 0.0598 (19) | 0.0565 (17) | −0.0167 (17) | 0.0080 (17) | −0.0020 (14) |
O2 | 0.123 (3) | 0.082 (2) | 0.0377 (17) | −0.004 (2) | 0.0167 (19) | −0.0153 (16) |
O3 | 0.071 (2) | 0.0596 (18) | 0.0273 (13) | −0.0036 (17) | 0.0002 (14) | 0.0029 (13) |
C1 | 0.051 (3) | 0.051 (3) | 0.0324 (19) | −0.003 (2) | 0.000 (2) | 0.0060 (18) |
C2 | 0.066 (3) | 0.060 (3) | 0.035 (2) | −0.003 (3) | 0.003 (2) | −0.005 (2) |
C3 | 0.067 (3) | 0.050 (3) | 0.040 (2) | −0.005 (2) | 0.004 (2) | −0.0136 (19) |
C4 | 0.040 (3) | 0.041 (2) | 0.0380 (19) | −0.004 (2) | −0.0008 (19) | −0.0044 (17) |
C5 | 0.031 (2) | 0.038 (2) | 0.0270 (16) | −0.0019 (19) | 0.0002 (17) | 0.0012 (15) |
C6 | 0.034 (2) | 0.043 (2) | 0.0321 (19) | 0.000 (2) | −0.0019 (19) | 0.0007 (17) |
C8 | 0.031 (2) | 0.040 (2) | 0.0308 (19) | 0.0043 (19) | 0.0005 (18) | −0.0018 (17) |
C9 | 0.034 (2) | 0.039 (2) | 0.0303 (19) | −0.001 (2) | 0.0020 (18) | 0.0023 (16) |
C10 | 0.033 (2) | 0.040 (2) | 0.0283 (18) | −0.0013 (19) | 0.0012 (17) | 0.0043 (18) |
C11 | 0.058 (3) | 0.038 (2) | 0.041 (2) | 0.006 (2) | −0.003 (2) | 0.0025 (17) |
C12 | 0.055 (3) | 0.035 (2) | 0.056 (2) | 0.003 (2) | 0.002 (2) | −0.0015 (19) |
C13 | 0.053 (3) | 0.049 (2) | 0.041 (2) | 0.000 (3) | 0.006 (2) | −0.007 (2) |
C14 | 0.036 (2) | 0.046 (2) | 0.0283 (18) | 0.000 (2) | 0.0008 (18) | −0.0010 (17) |
C15 | 0.057 (3) | 0.064 (3) | 0.069 (3) | −0.012 (3) | −0.006 (3) | −0.003 (3) |
C16 | 0.074 (3) | 0.052 (3) | 0.063 (3) | −0.006 (3) | −0.005 (3) | −0.014 (2) |
C17 | 0.058 (3) | 0.060 (3) | 0.038 (2) | −0.005 (3) | −0.001 (2) | −0.005 (2) |
C18 | 0.062 (3) | 0.042 (2) | 0.061 (3) | 0.008 (2) | 0.005 (2) | 0.000 (2) |
C19 | 0.054 (3) | 0.055 (3) | 0.058 (3) | −0.016 (2) | 0.000 (2) | −0.005 (2) |
C20 | 0.038 (2) | 0.065 (3) | 0.048 (2) | 0.001 (2) | −0.0044 (19) | 0.001 (2) |
C21 | 0.053 (3) | 0.053 (3) | 0.035 (2) | 0.004 (2) | 0.002 (2) | 0.007 (2) |
Geometric parameters (Å, º) top
F—C21 | 1.387 (5) | C9—C10 | 1.541 (5) |
O1—C15 | 1.412 (5) | C9—H9 | 0.98 |
O1—C12 | 1.439 (5) | C10—C20 | 1.541 (5) |
O2—C17 | 1.186 (4) | C11—C12 | 1.532 (5) |
O3—C17 | 1.386 (5) | C11—H11A | 0.97 |
O3—C21 | 1.422 (4) | C11—H11B | 0.97 |
C1—C2 | 1.530 (5) | C12—C13 | 1.532 (5) |
C1—C10 | 1.532 (5) | C12—H12 | 0.98 |
C1—H1A | 0.97 | C13—C16 | 1.524 (6) |
C1—H1B | 0.97 | C13—C14 | 1.525 (5) |
C2—C3 | 1.517 (5) | C13—H13 | 0.98 |
C2—H2A | 0.97 | C14—C17 | 1.499 (5) |
C2—H2B | 0.97 | C14—H14 | 0.98 |
C3—C4 | 1.539 (5) | C15—C16 | 1.520 (6) |
C3—H3A | 0.97 | C15—H15A | 0.97 |
C3—H3B | 0.97 | C15—H15B | 0.97 |
C4—C18 | 1.530 (5) | C16—H16A | 0.97 |
C4—C19 | 1.534 (6) | C16—H16B | 0.97 |
C4—C5 | 1.534 (5) | C18—H18A | 0.96 |
C5—C10 | 1.552 (5) | C18—H18B | 0.96 |
C5—C6 | 1.552 (4) | C18—H18C | 0.96 |
C5—H5 | 0.98 | C19—H19A | 0.96 |
C6—C21 | 1.511 (5) | C19—H19B | 0.96 |
C6—C8 | 1.538 (5) | C19—H19C | 0.96 |
C6—H6 | 0.98 | C20—H20A | 0.96 |
C8—C14 | 1.514 (5) | C20—H20B | 0.96 |
C8—C9 | 1.531 (4) | C20—H20C | 0.96 |
C8—H8 | 0.98 | C21—H21 | 0.98 |
C9—C11 | 1.523 (5) | | |
| | | |
C15—O1—C12 | 109.0 (3) | C12—C11—H11B | 109.7 |
C17—O3—C21 | 119.9 (3) | H11A—C11—H11B | 108.2 |
C2—C1—C10 | 111.2 (3) | O1—C12—C13 | 103.2 (3) |
C2—C1—H1A | 109.4 | O1—C12—C11 | 108.7 (3) |
C10—C1—H1A | 109.4 | C13—C12—C11 | 118.9 (3) |
C2—C1—H1B | 109.4 | O1—C12—H12 | 108.5 |
C10—C1—H1B | 109.4 | C13—C12—H12 | 108.5 |
H1A—C1—H1B | 108 | C11—C12—H12 | 108.5 |
C3—C2—C1 | 111.9 (3) | C16—C13—C14 | 113.6 (4) |
C3—C2—H2A | 109.2 | C16—C13—C12 | 100.6 (3) |
C1—C2—H2A | 109.2 | C14—C13—C12 | 111.3 (3) |
C3—C2—H2B | 109.2 | C16—C13—H13 | 110.3 |
C1—C2—H2B | 109.2 | C14—C13—H13 | 110.3 |
H2A—C2—H2B | 107.9 | C12—C13—H13 | 110.3 |
C2—C3—C4 | 116.3 (3) | C17—C14—C8 | 108.2 (3) |
C2—C3—H3A | 108.2 | C17—C14—C13 | 115.2 (3) |
C4—C3—H3A | 108.2 | C8—C14—C13 | 109.7 (3) |
C2—C3—H3B | 108.2 | C17—C14—H14 | 107.8 |
C4—C3—H3B | 108.2 | C8—C14—H14 | 107.8 |
H3A—C3—H3B | 107.4 | C13—C14—H14 | 107.8 |
C18—C4—C19 | 107.2 (3) | O1—C15—C16 | 107.8 (4) |
C18—C4—C5 | 110.1 (3) | O1—C15—H15A | 110.2 |
C19—C4—C5 | 114.6 (3) | C16—C15—H15A | 110.2 |
C18—C4—C3 | 108.3 (3) | O1—C15—H15B | 110.2 |
C19—C4—C3 | 110.9 (3) | C16—C15—H15B | 110.2 |
C5—C4—C3 | 105.7 (3) | H15A—C15—H15B | 108.5 |
C4—C5—C10 | 117.5 (3) | C15—C16—C13 | 102.4 (3) |
C4—C5—C6 | 121.7 (3) | C15—C16—H16A | 111.3 |
C10—C5—C6 | 103.9 (3) | C13—C16—H16A | 111.3 |
C4—C5—H5 | 103.9 | C15—C16—H16B | 111.3 |
C10—C5—H5 | 103.9 | C13—C16—H16B | 111.3 |
C6—C5—H5 | 103.9 | H16A—C16—H16B | 109.2 |
C21—C6—C8 | 110.3 (3) | O2—C17—O3 | 117.2 (4) |
C21—C6—C5 | 118.0 (3) | O2—C17—C14 | 128.4 (4) |
C8—C6—C5 | 103.8 (3) | O3—C17—C14 | 114.4 (3) |
C21—C6—H6 | 108.1 | C4—C18—H18A | 109.5 |
C8—C6—H6 | 108.1 | C4—C18—H18B | 109.5 |
C5—C6—H6 | 108.1 | H18A—C18—H18B | 109.5 |
C14—C8—C9 | 109.3 (3) | C4—C18—H18C | 109.5 |
C14—C8—C6 | 115.6 (3) | H18A—C18—H18C | 109.5 |
C9—C8—C6 | 106.4 (3) | H18B—C18—H18C | 109.5 |
C14—C8—H8 | 108.4 | C4—C19—H19A | 109.5 |
C9—C8—H8 | 108.4 | C4—C19—H19B | 109.5 |
C6—C8—H8 | 108.4 | H19A—C19—H19B | 109.5 |
C11—C9—C8 | 108.2 (3) | C4—C19—H19C | 109.5 |
C11—C9—C10 | 124.5 (3) | H19A—C19—H19C | 109.5 |
C8—C9—C10 | 102.2 (3) | H19B—C19—H19C | 109.5 |
C11—C9—H9 | 107 | C10—C20—H20A | 109.5 |
C8—C9—H9 | 107 | C10—C20—H20B | 109.5 |
C10—C9—H9 | 107 | H20A—C20—H20B | 109.5 |
C1—C10—C9 | 114.8 (3) | C10—C20—H20C | 109.5 |
C1—C10—C20 | 109.7 (3) | H20A—C20—H20C | 109.5 |
C9—C10—C20 | 109.4 (3) | H20B—C20—H20C | 109.5 |
C1—C10—C5 | 108.4 (3) | F—C21—O3 | 107.7 (3) |
C9—C10—C5 | 98.6 (2) | F—C21—C6 | 110.6 (3) |
C20—C10—C5 | 115.9 (3) | O3—C21—C6 | 112.0 (3) |
C9—C11—C12 | 109.8 (3) | F—C21—H21 | 108.8 |
C9—C11—H11A | 109.7 | O3—C21—H21 | 108.8 |
C12—C11—H11A | 109.7 | C6—C21—H21 | 108.8 |
C9—C11—H11B | 109.7 | | |
| | | |
C10—C1—C2—C3 | −54.7 (5) | C4—C5—C10—C20 | 67.3 (4) |
C1—C2—C3—C4 | 54.6 (5) | C6—C5—C10—C20 | −70.4 (4) |
C2—C3—C4—C18 | −168.4 (4) | C8—C9—C11—C12 | 55.0 (4) |
C2—C3—C4—C19 | 74.3 (4) | C10—C9—C11—C12 | 174.7 (3) |
C2—C3—C4—C5 | −50.5 (5) | C15—O1—C12—C13 | −30.4 (4) |
C18—C4—C5—C10 | 169.1 (3) | C15—O1—C12—C11 | −157.5 (3) |
C19—C4—C5—C10 | −70.0 (4) | C9—C11—C12—O1 | 74.1 (4) |
C3—C4—C5—C10 | 52.5 (4) | C9—C11—C12—C13 | −43.5 (5) |
C18—C4—C5—C6 | −61.1 (4) | O1—C12—C13—C16 | 40.7 (4) |
C19—C4—C5—C6 | 59.7 (4) | C11—C12—C13—C16 | 161.0 (4) |
C3—C4—C5—C6 | −177.8 (3) | O1—C12—C13—C14 | −80.0 (4) |
C4—C5—C6—C21 | 75.9 (5) | C11—C12—C13—C14 | 40.4 (5) |
C10—C5—C6—C21 | −148.8 (3) | C9—C8—C14—C17 | −168.3 (3) |
C4—C5—C6—C8 | −161.8 (3) | C6—C8—C14—C17 | −48.2 (4) |
C10—C5—C6—C8 | −26.4 (4) | C9—C8—C14—C13 | 65.3 (4) |
C21—C6—C8—C14 | 1.8 (5) | C6—C8—C14—C13 | −174.7 (3) |
C5—C6—C8—C14 | −125.6 (3) | C16—C13—C14—C17 | 75.8 (4) |
C21—C6—C8—C9 | 123.3 (3) | C12—C13—C14—C17 | −171.5 (4) |
C5—C6—C8—C9 | −4.0 (4) | C16—C13—C14—C8 | −161.9 (3) |
C14—C8—C9—C11 | −68.6 (4) | C12—C13—C14—C8 | −49.1 (4) |
C6—C8—C9—C11 | 165.9 (3) | C12—O1—C15—C16 | 7.3 (4) |
C14—C8—C9—C10 | 158.5 (3) | O1—C15—C16—C13 | 18.9 (5) |
C6—C8—C9—C10 | 33.0 (4) | C14—C13—C16—C15 | 83.5 (4) |
C2—C1—C10—C9 | 163.0 (3) | C12—C13—C16—C15 | −35.6 (4) |
C2—C1—C10—C20 | −73.4 (4) | C21—O3—C17—O2 | 175.2 (4) |
C2—C1—C10—C5 | 53.9 (4) | C21—O3—C17—C14 | −2.7 (6) |
C11—C9—C10—C1 | 74.7 (5) | C8—C14—C17—O2 | −127.6 (5) |
C8—C9—C10—C1 | −162.9 (3) | C13—C14—C17—O2 | −4.4 (7) |
C11—C9—C10—C20 | −49.1 (5) | C8—C14—C17—O3 | 50.1 (5) |
C8—C9—C10—C20 | 73.3 (4) | C13—C14—C17—O3 | 173.2 (4) |
C11—C9—C10—C5 | −170.4 (3) | C17—O3—C21—F | 73.8 (4) |
C8—C9—C10—C5 | −48.0 (3) | C17—O3—C21—C6 | −48.0 (5) |
C4—C5—C10—C1 | −56.5 (4) | C8—C6—C21—F | −74.4 (4) |
C6—C5—C10—C1 | 165.9 (3) | C5—C6—C21—F | 44.6 (4) |
C4—C5—C10—C9 | −176.3 (3) | C8—C6—C21—O3 | 45.7 (4) |
C6—C5—C10—C9 | 46.1 (3) | C5—C6—C21—O3 | 164.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O3i | 0.98 | 2.65 | 3.449 (5) | 139 |
C18—H18A···O2ii | 0.96 | 2.76 | 3.684 (5) | 161 |
C21—H21···O2ii | 0.98 | 2.77 | 3.560 (6) | 138 |
C20—H20A···Fiii | 0.96 | 2.68 | 3.619 (4) | 166 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2; (iii) x−1, y, z. |