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The structure of the title compound, C22H28O5, which is a natural furan ­diterpene, has been determined. The crystal structure is stabilized by C—H...O intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014394/hg6058sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014394/hg6058Isup2.hkl
Contains datablock I

CCDC reference: 245305

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.117
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT024_ALERT_4_C Merging of Friedel Data Preferred for Z<=Si .... ! PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C19 .. 5.32 su PLAT320_ALERT_2_C Check Hybridisation of C14 in Main Residue . ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H19A .. O1 .. 2.69 Ang.
Alert level G REFLT03_ALERT_4_G ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 3320 Count of symmetry unique reflns 1928 Completeness (_total/calc) 172.20% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1392 Fraction of Friedel pairs measured 0.722 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997); 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 (CCDC, 2003); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

(I) top
Crystal data top
C22H28O5F(000) = 800
Mr = 372.44Dx = 1.299 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4243 reflections
a = 9.6398 (3) Åθ = 1.0–27.5°
b = 11.5164 (4) ŵ = 0.09 mm1
c = 17.1539 (5) ÅT = 293 K
V = 1904.35 (10) Å3Prism, colourless
Z = 40.16 × 0.11 × 0.06 mm
Data collection top
Nonius KappaCCD
diffractometer
Rint = 0.037
CCD rotation images, thick slices scansθmax = 25°, θmin = 3.0°
5957 measured reflectionsh = 1111
3320 independent reflectionsk = 1312
2683 reflections with I > 2σ(I)l = 2020
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0483P)2 + 0.3858P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.047(Δ/σ)max = 0.004
wR(F2) = 0.117Δρmax = 0.14 e Å3
S = 1.04Δρmin = 0.13 e Å3
3320 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
249 parametersExtinction coefficient: 0.014 (4)
0 restraints
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
xyzUiso*/Ueq
O10.7537 (2)0.84205 (17)1.32519 (11)0.0613 (5)
O20.57784 (18)0.65909 (15)0.90661 (9)0.0464 (4)
O30.6301 (2)0.87406 (14)0.99654 (11)0.0536 (5)
O40.6707 (3)1.04871 (17)1.04909 (14)0.0769 (7)
O50.7732 (2)0.7147 (2)0.84580 (12)0.0745 (7)
C10.6272 (3)0.4422 (2)1.15913 (16)0.0530 (7)
H1A0.67350.44111.20930.064*
H1B0.52820.44831.16870.064*
C20.6564 (4)0.3285 (2)1.11700 (17)0.0641 (8)
H2A0.75560.31891.11010.077*
H2B0.62240.26391.14780.077*
C30.5851 (4)0.3294 (2)1.03821 (18)0.0650 (8)
H3A0.48570.33411.04660.078*
H3B0.60390.25621.01240.078*
C40.6282 (3)0.4284 (2)0.98357 (16)0.0491 (7)
C50.6087 (3)0.5461 (2)1.02893 (13)0.0390 (5)
H5A0.50850.55211.03780.047*
C60.6468 (3)0.6569 (2)0.98186 (14)0.0402 (5)
H6A0.74750.66250.97520.048*
C70.5936 (3)0.7593 (2)1.02669 (14)0.0412 (6)
H7A0.49240.75361.03060.049*
C80.6531 (3)0.76273 (19)1.10607 (14)0.0392 (6)
H8A0.75420.76411.10020.047*
C90.6185 (3)0.6596 (2)1.15629 (14)0.0406 (5)
H9A0.51720.6531.15860.049*
C100.6753 (3)0.5499 (2)1.11344 (13)0.0399 (6)
C110.6723 (3)0.6822 (2)1.24110 (15)0.0524 (7)
H11A0.60470.65331.27830.063*
H11B0.75820.641.24910.063*
C120.6966 (3)0.8094 (2)1.25530 (15)0.0494 (7)
C130.6755 (3)0.9032 (2)1.20995 (16)0.0476 (6)
C140.6093 (3)0.88313 (19)1.13275 (15)0.0451 (6)
H14A0.50850.88321.13990.054*
C150.7211 (3)1.0021 (3)1.25364 (18)0.0577 (7)
H15A0.71951.07931.23780.069*
C160.7665 (3)0.9607 (3)1.32195 (19)0.0664 (8)
H16A0.80191.00641.3620.08*
C170.6421 (3)0.9490 (2)1.05938 (17)0.0536 (7)
C180.5274 (4)0.4181 (3)0.9140 (2)0.0755 (10)
H18A0.43660.44280.92980.113*
H18B0.52360.33880.89690.113*
H18C0.55940.46630.8720.113*
C190.7747 (3)0.4101 (3)0.95217 (18)0.0673 (9)
H19A0.77590.34330.91870.101*
H19B0.83740.39820.99490.101*
H19C0.80280.47740.92310.101*
C200.8352 (3)0.5521 (2)1.11202 (15)0.0460 (6)
H20A0.86630.60251.0710.069*
H20B0.86970.4751.10310.069*
H20C0.86920.58011.16110.069*
C210.6519 (3)0.6930 (2)0.84394 (15)0.0488 (6)
C220.5615 (3)0.6998 (3)0.77351 (15)0.0655 (9)
H22A0.50660.63050.76970.098*
H22B0.61820.70730.72780.098*
H22C0.50140.7660.77770.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0734 (14)0.0664 (12)0.0441 (10)0.0026 (12)0.0001 (10)0.0104 (9)
O20.0456 (10)0.0541 (10)0.0395 (9)0.0050 (9)0.0044 (8)0.0020 (8)
O30.0721 (13)0.0377 (9)0.0510 (10)0.0007 (9)0.0108 (9)0.0097 (8)
O40.1074 (18)0.0352 (10)0.0879 (15)0.0048 (12)0.0136 (13)0.0106 (11)
O50.0530 (14)0.1131 (19)0.0573 (12)0.0097 (13)0.0010 (10)0.0190 (12)
C10.0652 (18)0.0407 (13)0.0531 (15)0.0010 (14)0.0093 (14)0.0100 (12)
C20.090 (2)0.0365 (14)0.0656 (19)0.0008 (15)0.0040 (17)0.0055 (13)
C30.082 (2)0.0375 (14)0.075 (2)0.0036 (16)0.0026 (18)0.0051 (13)
C40.0562 (16)0.0390 (14)0.0519 (15)0.0010 (12)0.0030 (13)0.0066 (11)
C50.0378 (12)0.0354 (11)0.0439 (13)0.0007 (11)0.0000 (10)0.0005 (10)
C60.0382 (13)0.0423 (13)0.0402 (13)0.0001 (11)0.0046 (10)0.0015 (11)
C70.0433 (14)0.0343 (12)0.0462 (13)0.0003 (11)0.0045 (12)0.0064 (10)
C80.0415 (14)0.0346 (12)0.0414 (13)0.0016 (10)0.0000 (11)0.0006 (10)
C90.0440 (13)0.0355 (11)0.0424 (13)0.0017 (11)0.0047 (11)0.0027 (10)
C100.0460 (13)0.0364 (12)0.0373 (12)0.0035 (12)0.0023 (11)0.0030 (10)
C110.0687 (18)0.0497 (15)0.0389 (13)0.0022 (14)0.0057 (13)0.0004 (11)
C120.0524 (16)0.0564 (16)0.0396 (13)0.0006 (13)0.0029 (12)0.0080 (12)
C130.0489 (15)0.0434 (13)0.0506 (14)0.0026 (13)0.0036 (12)0.0071 (12)
C140.0471 (15)0.0343 (12)0.0540 (14)0.0040 (11)0.0025 (12)0.0018 (11)
C150.0573 (18)0.0499 (15)0.0659 (18)0.0038 (14)0.0046 (15)0.0127 (13)
C160.068 (2)0.0682 (19)0.0626 (19)0.0087 (18)0.0041 (16)0.0234 (17)
C170.0619 (18)0.0353 (13)0.0635 (17)0.0035 (13)0.0123 (14)0.0039 (13)
C180.092 (3)0.0551 (17)0.079 (2)0.0018 (18)0.0280 (19)0.0156 (16)
C190.079 (2)0.0608 (17)0.0617 (18)0.0158 (17)0.0022 (16)0.0191 (15)
C200.0441 (14)0.0472 (14)0.0466 (14)0.0054 (12)0.0002 (11)0.0015 (12)
C210.0485 (17)0.0554 (15)0.0425 (14)0.0054 (13)0.0022 (12)0.0016 (12)
C220.067 (2)0.087 (2)0.0421 (15)0.0071 (18)0.0061 (14)0.0003 (15)
Geometric parameters (Å, º) top
O1—C121.372 (3)C8—H8A0.98
O1—C161.374 (4)C9—C101.561 (3)
O2—C211.348 (3)C9—C111.566 (4)
O2—C61.452 (3)C9—H9A0.98
O3—C171.386 (3)C10—C201.542 (3)
O3—C71.463 (3)C11—C121.504 (4)
O4—C171.194 (3)C11—H11A0.97
O5—C211.196 (3)C11—H11B0.97
C1—C21.522 (4)C12—C131.347 (4)
C1—C101.539 (3)C13—C151.432 (4)
C1—H1A0.97C13—C141.488 (4)
C1—H1B0.97C14—C171.503 (4)
C2—C31.516 (4)C14—H14A0.98
C2—H2A0.97C15—C161.338 (4)
C2—H2B0.97C15—H15A0.93
C3—C41.534 (4)C16—H16A0.93
C3—H3A0.97C18—H18A0.96
C3—H3B0.97C18—H18B0.96
C4—C191.526 (4)C18—H18C0.96
C4—C181.544 (4)C19—H19A0.96
C4—C51.574 (3)C19—H19B0.96
C5—C61.555 (3)C19—H19C0.96
C5—C101.586 (3)C20—H20A0.96
C5—H5A0.98C20—H20B0.96
C6—C71.498 (3)C20—H20C0.96
C6—H6A0.98C21—C221.492 (4)
C7—C81.478 (3)C22—H22A0.96
C7—H7A0.98C22—H22B0.96
C8—C91.504 (3)C22—H22C0.96
C8—C141.520 (3)
C12—O1—C16105.9 (2)C20—C10—C9110.2 (2)
C21—O2—C6118.1 (2)C1—C10—C5108.7 (2)
C17—O3—C7107.94 (19)C20—C10—C5113.0 (2)
C2—C1—C10113.3 (2)C9—C10—C5108.11 (19)
C2—C1—H1A108.9C12—C11—C9111.3 (2)
C10—C1—H1A108.9C12—C11—H11A109.4
C2—C1—H1B108.9C9—C11—H11A109.4
C10—C1—H1B108.9C12—C11—H11B109.4
H1A—C1—H1B107.7C9—C11—H11B109.4
C3—C2—C1109.5 (2)H11A—C11—H11B108
C3—C2—H2A109.8C13—C12—O1110.2 (2)
C1—C2—H2A109.8C13—C12—C11131.7 (2)
C3—C2—H2B109.8O1—C12—C11118.1 (2)
C1—C2—H2B109.8C12—C13—C15106.8 (3)
H2A—C2—H2B108.2C12—C13—C14117.0 (2)
C2—C3—C4115.3 (2)C15—C13—C14136.1 (3)
C2—C3—H3A108.5C13—C14—C17125.2 (2)
C4—C3—H3A108.5C13—C14—C8106.9 (2)
C2—C3—H3B108.5C17—C14—C898.6 (2)
C4—C3—H3B108.5C13—C14—H14A108.3
H3A—C3—H3B107.5C17—C14—H14A108.3
C19—C4—C3111.3 (2)C8—C14—H14A108.3
C19—C4—C18107.4 (2)C16—C15—C13106.0 (3)
C3—C4—C18104.2 (2)C16—C15—H15A127
C19—C4—C5113.8 (2)C13—C15—H15A127
C3—C4—C5107.8 (2)C15—C16—O1111.1 (3)
C18—C4—C5111.9 (2)C15—C16—H16A124.4
C6—C5—C4114.96 (19)O1—C16—H16A124.4
C6—C5—C10110.86 (19)O4—C17—O3120.2 (3)
C4—C5—C10115.31 (19)O4—C17—C14131.1 (3)
C6—C5—H5A104.8O3—C17—C14108.6 (2)
C4—C5—H5A104.8C4—C18—H18A109.5
C10—C5—H5A104.8C4—C18—H18B109.5
O2—C6—C7106.62 (19)H18A—C18—H18B109.5
O2—C6—C5111.56 (19)C4—C18—H18C109.5
C7—C6—C5107.37 (19)H18A—C18—H18C109.5
O2—C6—H6A110.4H18B—C18—H18C109.5
C7—C6—H6A110.4C4—C19—H19A109.5
C5—C6—H6A110.4C4—C19—H19B109.5
O3—C7—C8102.01 (19)H19A—C19—H19B109.5
O3—C7—C6116.6 (2)C4—C19—H19C109.5
C8—C7—C6111.2 (2)H19A—C19—H19C109.5
O3—C7—H7A108.9H19B—C19—H19C109.5
C8—C7—H7A108.9C10—C20—H20A109.5
C6—C7—H7A108.9C10—C20—H20B109.5
C7—C8—C9114.8 (2)H20A—C20—H20B109.5
C7—C8—C14101.21 (19)C10—C20—H20C109.5
C9—C8—C14119.1 (2)H20A—C20—H20C109.5
C7—C8—H8A107H20B—C20—H20C109.5
C9—C8—H8A107O5—C21—O2123.8 (3)
C14—C8—H8A107O5—C21—C22125.6 (3)
C8—C9—C10106.94 (19)O2—C21—C22110.6 (2)
C8—C9—C11109.1 (2)C21—C22—H22A109.5
C10—C9—C11117.1 (2)C21—C22—H22B109.5
C8—C9—H9A107.8H22A—C22—H22B109.5
C10—C9—H9A107.8C21—C22—H22C109.5
C11—C9—H9A107.8H22A—C22—H22C109.5
C1—C10—C20108.8 (2)H22B—C22—H22C109.5
C1—C10—C9107.87 (19)
C10—C1—C2—C358.3 (4)C8—C9—C10—C556.5 (3)
C1—C2—C3—C458.8 (4)C11—C9—C10—C5179.2 (2)
C2—C3—C4—C1971.9 (3)C6—C5—C10—C1176.6 (2)
C2—C3—C4—C18172.6 (3)C4—C5—C10—C150.6 (3)
C2—C3—C4—C553.6 (3)C6—C5—C10—C2062.5 (3)
C19—C4—C5—C656.4 (3)C4—C5—C10—C2070.3 (3)
C3—C4—C5—C6179.6 (2)C6—C5—C10—C959.7 (3)
C18—C4—C5—C665.6 (3)C4—C5—C10—C9167.48 (19)
C19—C4—C5—C1074.5 (3)C8—C9—C11—C1219.4 (3)
C3—C4—C5—C1049.5 (3)C10—C9—C11—C12141.0 (2)
C18—C4—C5—C10163.5 (2)C16—O1—C12—C130.5 (3)
C21—O2—C6—C7105.7 (2)C16—O1—C12—C11179.0 (3)
C21—O2—C6—C5137.4 (2)C9—C11—C12—C132.8 (4)
C4—C5—C6—O251.5 (3)C9—C11—C12—O1175.2 (2)
C10—C5—C6—O2175.52 (19)O1—C12—C13—C150.4 (3)
C4—C5—C6—C7168.0 (2)C11—C12—C13—C15178.6 (3)
C10—C5—C6—C759.0 (3)O1—C12—C13—C14178.0 (2)
C17—O3—C7—C826.9 (3)C11—C12—C13—C143.8 (5)
C17—O3—C7—C6148.2 (2)C12—C13—C14—C17144.8 (3)
O2—C6—C7—O366.1 (3)C15—C13—C14—C1738.5 (5)
C5—C6—C7—O3174.2 (2)C12—C13—C14—C830.8 (3)
O2—C6—C7—C8177.63 (19)C15—C13—C14—C8152.5 (3)
C5—C6—C7—C857.9 (3)C7—C8—C14—C13174.3 (2)
O3—C7—C8—C9173.5 (2)C9—C8—C14—C1358.8 (3)
C6—C7—C8—C961.6 (3)C7—C8—C14—C1743.3 (2)
O3—C7—C8—C1443.9 (2)C9—C8—C14—C17170.2 (2)
C6—C7—C8—C14168.8 (2)C12—C13—C15—C160.1 (3)
C7—C8—C9—C1059.4 (3)C14—C13—C15—C16177.0 (3)
C14—C8—C9—C10179.6 (2)C13—C15—C16—O10.2 (4)
C7—C8—C9—C11173.0 (2)C12—O1—C16—C150.5 (3)
C14—C8—C9—C1152.9 (3)C7—O3—C17—O4179.6 (3)
C2—C1—C10—C2069.4 (3)C7—O3—C17—C141.4 (3)
C2—C1—C10—C9171.1 (2)C13—C14—C17—O436.2 (5)
C2—C1—C10—C554.1 (3)C8—C14—C17—O4154.1 (3)
C8—C9—C10—C1173.9 (2)C13—C14—C17—O3145.9 (2)
C11—C9—C10—C163.4 (3)C8—C14—C17—O328.0 (3)
C8—C9—C10—C2067.5 (2)C6—O2—C21—O54.7 (4)
C11—C9—C10—C2055.3 (3)C6—O2—C21—C22175.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···O4i0.962.593.517 (5)162
C14—H14A···O5i0.982.543.450 (4)154
C3—H3B···O4ii0.972.553.342 (3)138
C19—H19A···O1iii0.962.693.641 (4)173
Symmetry codes: (i) x1/2, y+3/2, z+2; (ii) x, y1, z; (iii) x+3/2, y+1, z1/2.
 

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