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The structure of the title compound, C
22H
28O
5, which is a natural furan diterpene, has been determined. The crystal structure is stabilized by C—H
O intermolecular interactions.
Supporting information
CCDC reference: 245305
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
Crystal data top
C22H28O5 | F(000) = 800 |
Mr = 372.44 | Dx = 1.299 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4243 reflections |
a = 9.6398 (3) Å | θ = 1.0–27.5° |
b = 11.5164 (4) Å | µ = 0.09 mm−1 |
c = 17.1539 (5) Å | T = 293 K |
V = 1904.35 (10) Å3 | Prism, colourless |
Z = 4 | 0.16 × 0.11 × 0.06 mm |
Data collection top
Nonius KappaCCD diffractometer | Rint = 0.037 |
CCD rotation images, thick slices scans | θmax = 25°, θmin = 3.0° |
5957 measured reflections | h = −11→11 |
3320 independent reflections | k = −13→12 |
2683 reflections with I > 2σ(I) | l = −20→20 |
Refinement top
Refinement on F2 | H-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) = 0.117 | Δρmax = 0.14 e Å−3 |
S = 1.04 | Δρmin = −0.13 e Å−3 |
3320 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
249 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.7537 (2) | 0.84205 (17) | 1.32519 (11) | 0.0613 (5) | |
O2 | 0.57784 (18) | 0.65909 (15) | 0.90661 (9) | 0.0464 (4) | |
O3 | 0.6301 (2) | 0.87406 (14) | 0.99654 (11) | 0.0536 (5) | |
O4 | 0.6707 (3) | 1.04871 (17) | 1.04909 (14) | 0.0769 (7) | |
O5 | 0.7732 (2) | 0.7147 (2) | 0.84580 (12) | 0.0745 (7) | |
C1 | 0.6272 (3) | 0.4422 (2) | 1.15913 (16) | 0.0530 (7) | |
H1A | 0.6735 | 0.4411 | 1.2093 | 0.064* | |
H1B | 0.5282 | 0.4483 | 1.1687 | 0.064* | |
C2 | 0.6564 (4) | 0.3285 (2) | 1.11700 (17) | 0.0641 (8) | |
H2A | 0.7556 | 0.3189 | 1.1101 | 0.077* | |
H2B | 0.6224 | 0.2639 | 1.1478 | 0.077* | |
C3 | 0.5851 (4) | 0.3294 (2) | 1.03821 (18) | 0.0650 (8) | |
H3A | 0.4857 | 0.3341 | 1.0466 | 0.078* | |
H3B | 0.6039 | 0.2562 | 1.0124 | 0.078* | |
C4 | 0.6282 (3) | 0.4284 (2) | 0.98357 (16) | 0.0491 (7) | |
C5 | 0.6087 (3) | 0.5461 (2) | 1.02893 (13) | 0.0390 (5) | |
H5A | 0.5085 | 0.5521 | 1.0378 | 0.047* | |
C6 | 0.6468 (3) | 0.6569 (2) | 0.98186 (14) | 0.0402 (5) | |
H6A | 0.7475 | 0.6625 | 0.9752 | 0.048* | |
C7 | 0.5936 (3) | 0.7593 (2) | 1.02669 (14) | 0.0412 (6) | |
H7A | 0.4924 | 0.7536 | 1.0306 | 0.049* | |
C8 | 0.6531 (3) | 0.76273 (19) | 1.10607 (14) | 0.0392 (6) | |
H8A | 0.7542 | 0.7641 | 1.1002 | 0.047* | |
C9 | 0.6185 (3) | 0.6596 (2) | 1.15629 (14) | 0.0406 (5) | |
H9A | 0.5172 | 0.653 | 1.1586 | 0.049* | |
C10 | 0.6753 (3) | 0.5499 (2) | 1.11344 (13) | 0.0399 (6) | |
C11 | 0.6723 (3) | 0.6822 (2) | 1.24110 (15) | 0.0524 (7) | |
H11A | 0.6047 | 0.6533 | 1.2783 | 0.063* | |
H11B | 0.7582 | 0.64 | 1.2491 | 0.063* | |
C12 | 0.6966 (3) | 0.8094 (2) | 1.25530 (15) | 0.0494 (7) | |
C13 | 0.6755 (3) | 0.9032 (2) | 1.20995 (16) | 0.0476 (6) | |
C14 | 0.6093 (3) | 0.88313 (19) | 1.13275 (15) | 0.0451 (6) | |
H14A | 0.5085 | 0.8832 | 1.1399 | 0.054* | |
C15 | 0.7211 (3) | 1.0021 (3) | 1.25364 (18) | 0.0577 (7) | |
H15A | 0.7195 | 1.0793 | 1.2378 | 0.069* | |
C16 | 0.7665 (3) | 0.9607 (3) | 1.32195 (19) | 0.0664 (8) | |
H16A | 0.8019 | 1.0064 | 1.362 | 0.08* | |
C17 | 0.6421 (3) | 0.9490 (2) | 1.05938 (17) | 0.0536 (7) | |
C18 | 0.5274 (4) | 0.4181 (3) | 0.9140 (2) | 0.0755 (10) | |
H18A | 0.4366 | 0.4428 | 0.9298 | 0.113* | |
H18B | 0.5236 | 0.3388 | 0.8969 | 0.113* | |
H18C | 0.5594 | 0.4663 | 0.872 | 0.113* | |
C19 | 0.7747 (3) | 0.4101 (3) | 0.95217 (18) | 0.0673 (9) | |
H19A | 0.7759 | 0.3433 | 0.9187 | 0.101* | |
H19B | 0.8374 | 0.3982 | 0.9949 | 0.101* | |
H19C | 0.8028 | 0.4774 | 0.9231 | 0.101* | |
C20 | 0.8352 (3) | 0.5521 (2) | 1.11202 (15) | 0.0460 (6) | |
H20A | 0.8663 | 0.6025 | 1.071 | 0.069* | |
H20B | 0.8697 | 0.475 | 1.1031 | 0.069* | |
H20C | 0.8692 | 0.5801 | 1.1611 | 0.069* | |
C21 | 0.6519 (3) | 0.6930 (2) | 0.84394 (15) | 0.0488 (6) | |
C22 | 0.5615 (3) | 0.6998 (3) | 0.77351 (15) | 0.0655 (9) | |
H22A | 0.5066 | 0.6305 | 0.7697 | 0.098* | |
H22B | 0.6182 | 0.7073 | 0.7278 | 0.098* | |
H22C | 0.5014 | 0.766 | 0.7777 | 0.098* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0734 (14) | 0.0664 (12) | 0.0441 (10) | −0.0026 (12) | −0.0001 (10) | −0.0104 (9) |
O2 | 0.0456 (10) | 0.0541 (10) | 0.0395 (9) | −0.0050 (9) | −0.0044 (8) | 0.0020 (8) |
O3 | 0.0721 (13) | 0.0377 (9) | 0.0510 (10) | −0.0007 (9) | −0.0108 (9) | 0.0097 (8) |
O4 | 0.1074 (18) | 0.0352 (10) | 0.0879 (15) | −0.0048 (12) | −0.0136 (13) | 0.0106 (11) |
O5 | 0.0530 (14) | 0.1131 (19) | 0.0573 (12) | −0.0097 (13) | 0.0010 (10) | 0.0190 (12) |
C1 | 0.0652 (18) | 0.0407 (13) | 0.0531 (15) | −0.0010 (14) | 0.0093 (14) | 0.0100 (12) |
C2 | 0.090 (2) | 0.0365 (14) | 0.0656 (19) | 0.0008 (15) | 0.0040 (17) | 0.0055 (13) |
C3 | 0.082 (2) | 0.0375 (14) | 0.075 (2) | −0.0036 (16) | −0.0026 (18) | −0.0051 (13) |
C4 | 0.0562 (16) | 0.0390 (14) | 0.0519 (15) | 0.0010 (12) | −0.0030 (13) | −0.0066 (11) |
C5 | 0.0378 (12) | 0.0354 (11) | 0.0439 (13) | −0.0007 (11) | 0.0000 (10) | −0.0005 (10) |
C6 | 0.0382 (13) | 0.0423 (13) | 0.0402 (13) | −0.0001 (11) | −0.0046 (10) | 0.0015 (11) |
C7 | 0.0433 (14) | 0.0343 (12) | 0.0462 (13) | 0.0003 (11) | −0.0045 (12) | 0.0064 (10) |
C8 | 0.0415 (14) | 0.0346 (12) | 0.0414 (13) | 0.0016 (10) | 0.0000 (11) | −0.0006 (10) |
C9 | 0.0440 (13) | 0.0355 (11) | 0.0424 (13) | 0.0017 (11) | 0.0047 (11) | 0.0027 (10) |
C10 | 0.0460 (13) | 0.0364 (12) | 0.0373 (12) | 0.0035 (12) | 0.0023 (11) | 0.0030 (10) |
C11 | 0.0687 (18) | 0.0497 (15) | 0.0389 (13) | 0.0022 (14) | 0.0057 (13) | 0.0004 (11) |
C12 | 0.0524 (16) | 0.0564 (16) | 0.0396 (13) | 0.0006 (13) | 0.0029 (12) | −0.0080 (12) |
C13 | 0.0489 (15) | 0.0434 (13) | 0.0506 (14) | 0.0026 (13) | 0.0036 (12) | −0.0071 (12) |
C14 | 0.0471 (15) | 0.0343 (12) | 0.0540 (14) | 0.0040 (11) | −0.0025 (12) | −0.0018 (11) |
C15 | 0.0573 (18) | 0.0499 (15) | 0.0659 (18) | −0.0038 (14) | 0.0046 (15) | −0.0127 (13) |
C16 | 0.068 (2) | 0.0682 (19) | 0.0626 (19) | −0.0087 (18) | 0.0041 (16) | −0.0234 (17) |
C17 | 0.0619 (18) | 0.0353 (13) | 0.0635 (17) | 0.0035 (13) | −0.0123 (14) | 0.0039 (13) |
C18 | 0.092 (3) | 0.0551 (17) | 0.079 (2) | −0.0018 (18) | −0.0280 (19) | −0.0156 (16) |
C19 | 0.079 (2) | 0.0608 (17) | 0.0617 (18) | 0.0158 (17) | 0.0022 (16) | −0.0191 (15) |
C20 | 0.0441 (14) | 0.0472 (14) | 0.0466 (14) | 0.0054 (12) | −0.0002 (11) | 0.0015 (12) |
C21 | 0.0485 (17) | 0.0554 (15) | 0.0425 (14) | 0.0054 (13) | −0.0022 (12) | 0.0016 (12) |
C22 | 0.067 (2) | 0.087 (2) | 0.0421 (15) | 0.0071 (18) | −0.0061 (14) | 0.0003 (15) |
Geometric parameters (Å, º) top
O1—C12 | 1.372 (3) | C8—H8A | 0.98 |
O1—C16 | 1.374 (4) | C9—C10 | 1.561 (3) |
O2—C21 | 1.348 (3) | C9—C11 | 1.566 (4) |
O2—C6 | 1.452 (3) | C9—H9A | 0.98 |
O3—C17 | 1.386 (3) | C10—C20 | 1.542 (3) |
O3—C7 | 1.463 (3) | C11—C12 | 1.504 (4) |
O4—C17 | 1.194 (3) | C11—H11A | 0.97 |
O5—C21 | 1.196 (3) | C11—H11B | 0.97 |
C1—C2 | 1.522 (4) | C12—C13 | 1.347 (4) |
C1—C10 | 1.539 (3) | C13—C15 | 1.432 (4) |
C1—H1A | 0.97 | C13—C14 | 1.488 (4) |
C1—H1B | 0.97 | C14—C17 | 1.503 (4) |
C2—C3 | 1.516 (4) | C14—H14A | 0.98 |
C2—H2A | 0.97 | C15—C16 | 1.338 (4) |
C2—H2B | 0.97 | C15—H15A | 0.93 |
C3—C4 | 1.534 (4) | C16—H16A | 0.93 |
C3—H3A | 0.97 | C18—H18A | 0.96 |
C3—H3B | 0.97 | C18—H18B | 0.96 |
C4—C19 | 1.526 (4) | C18—H18C | 0.96 |
C4—C18 | 1.544 (4) | C19—H19A | 0.96 |
C4—C5 | 1.574 (3) | C19—H19B | 0.96 |
C5—C6 | 1.555 (3) | C19—H19C | 0.96 |
C5—C10 | 1.586 (3) | C20—H20A | 0.96 |
C5—H5A | 0.98 | C20—H20B | 0.96 |
C6—C7 | 1.498 (3) | C20—H20C | 0.96 |
C6—H6A | 0.98 | C21—C22 | 1.492 (4) |
C7—C8 | 1.478 (3) | C22—H22A | 0.96 |
C7—H7A | 0.98 | C22—H22B | 0.96 |
C8—C9 | 1.504 (3) | C22—H22C | 0.96 |
C8—C14 | 1.520 (3) | | |
| | | |
C12—O1—C16 | 105.9 (2) | C20—C10—C9 | 110.2 (2) |
C21—O2—C6 | 118.1 (2) | C1—C10—C5 | 108.7 (2) |
C17—O3—C7 | 107.94 (19) | C20—C10—C5 | 113.0 (2) |
C2—C1—C10 | 113.3 (2) | C9—C10—C5 | 108.11 (19) |
C2—C1—H1A | 108.9 | C12—C11—C9 | 111.3 (2) |
C10—C1—H1A | 108.9 | C12—C11—H11A | 109.4 |
C2—C1—H1B | 108.9 | C9—C11—H11A | 109.4 |
C10—C1—H1B | 108.9 | C12—C11—H11B | 109.4 |
H1A—C1—H1B | 107.7 | C9—C11—H11B | 109.4 |
C3—C2—C1 | 109.5 (2) | H11A—C11—H11B | 108 |
C3—C2—H2A | 109.8 | C13—C12—O1 | 110.2 (2) |
C1—C2—H2A | 109.8 | C13—C12—C11 | 131.7 (2) |
C3—C2—H2B | 109.8 | O1—C12—C11 | 118.1 (2) |
C1—C2—H2B | 109.8 | C12—C13—C15 | 106.8 (3) |
H2A—C2—H2B | 108.2 | C12—C13—C14 | 117.0 (2) |
C2—C3—C4 | 115.3 (2) | C15—C13—C14 | 136.1 (3) |
C2—C3—H3A | 108.5 | C13—C14—C17 | 125.2 (2) |
C4—C3—H3A | 108.5 | C13—C14—C8 | 106.9 (2) |
C2—C3—H3B | 108.5 | C17—C14—C8 | 98.6 (2) |
C4—C3—H3B | 108.5 | C13—C14—H14A | 108.3 |
H3A—C3—H3B | 107.5 | C17—C14—H14A | 108.3 |
C19—C4—C3 | 111.3 (2) | C8—C14—H14A | 108.3 |
C19—C4—C18 | 107.4 (2) | C16—C15—C13 | 106.0 (3) |
C3—C4—C18 | 104.2 (2) | C16—C15—H15A | 127 |
C19—C4—C5 | 113.8 (2) | C13—C15—H15A | 127 |
C3—C4—C5 | 107.8 (2) | C15—C16—O1 | 111.1 (3) |
C18—C4—C5 | 111.9 (2) | C15—C16—H16A | 124.4 |
C6—C5—C4 | 114.96 (19) | O1—C16—H16A | 124.4 |
C6—C5—C10 | 110.86 (19) | O4—C17—O3 | 120.2 (3) |
C4—C5—C10 | 115.31 (19) | O4—C17—C14 | 131.1 (3) |
C6—C5—H5A | 104.8 | O3—C17—C14 | 108.6 (2) |
C4—C5—H5A | 104.8 | C4—C18—H18A | 109.5 |
C10—C5—H5A | 104.8 | C4—C18—H18B | 109.5 |
O2—C6—C7 | 106.62 (19) | H18A—C18—H18B | 109.5 |
O2—C6—C5 | 111.56 (19) | C4—C18—H18C | 109.5 |
C7—C6—C5 | 107.37 (19) | H18A—C18—H18C | 109.5 |
O2—C6—H6A | 110.4 | H18B—C18—H18C | 109.5 |
C7—C6—H6A | 110.4 | C4—C19—H19A | 109.5 |
C5—C6—H6A | 110.4 | C4—C19—H19B | 109.5 |
O3—C7—C8 | 102.01 (19) | H19A—C19—H19B | 109.5 |
O3—C7—C6 | 116.6 (2) | C4—C19—H19C | 109.5 |
C8—C7—C6 | 111.2 (2) | H19A—C19—H19C | 109.5 |
O3—C7—H7A | 108.9 | H19B—C19—H19C | 109.5 |
C8—C7—H7A | 108.9 | C10—C20—H20A | 109.5 |
C6—C7—H7A | 108.9 | C10—C20—H20B | 109.5 |
C7—C8—C9 | 114.8 (2) | H20A—C20—H20B | 109.5 |
C7—C8—C14 | 101.21 (19) | C10—C20—H20C | 109.5 |
C9—C8—C14 | 119.1 (2) | H20A—C20—H20C | 109.5 |
C7—C8—H8A | 107 | H20B—C20—H20C | 109.5 |
C9—C8—H8A | 107 | O5—C21—O2 | 123.8 (3) |
C14—C8—H8A | 107 | O5—C21—C22 | 125.6 (3) |
C8—C9—C10 | 106.94 (19) | O2—C21—C22 | 110.6 (2) |
C8—C9—C11 | 109.1 (2) | C21—C22—H22A | 109.5 |
C10—C9—C11 | 117.1 (2) | C21—C22—H22B | 109.5 |
C8—C9—H9A | 107.8 | H22A—C22—H22B | 109.5 |
C10—C9—H9A | 107.8 | C21—C22—H22C | 109.5 |
C11—C9—H9A | 107.8 | H22A—C22—H22C | 109.5 |
C1—C10—C20 | 108.8 (2) | H22B—C22—H22C | 109.5 |
C1—C10—C9 | 107.87 (19) | | |
| | | |
C10—C1—C2—C3 | −58.3 (4) | C8—C9—C10—C5 | −56.5 (3) |
C1—C2—C3—C4 | 58.8 (4) | C11—C9—C10—C5 | −179.2 (2) |
C2—C3—C4—C19 | 71.9 (3) | C6—C5—C10—C1 | 176.6 (2) |
C2—C3—C4—C18 | −172.6 (3) | C4—C5—C10—C1 | −50.6 (3) |
C2—C3—C4—C5 | −53.6 (3) | C6—C5—C10—C20 | −62.5 (3) |
C19—C4—C5—C6 | 56.4 (3) | C4—C5—C10—C20 | 70.3 (3) |
C3—C4—C5—C6 | −179.6 (2) | C6—C5—C10—C9 | 59.7 (3) |
C18—C4—C5—C6 | −65.6 (3) | C4—C5—C10—C9 | −167.48 (19) |
C19—C4—C5—C10 | −74.5 (3) | C8—C9—C11—C12 | 19.4 (3) |
C3—C4—C5—C10 | 49.5 (3) | C10—C9—C11—C12 | 141.0 (2) |
C18—C4—C5—C10 | 163.5 (2) | C16—O1—C12—C13 | 0.5 (3) |
C21—O2—C6—C7 | 105.7 (2) | C16—O1—C12—C11 | 179.0 (3) |
C21—O2—C6—C5 | −137.4 (2) | C9—C11—C12—C13 | 2.8 (4) |
C4—C5—C6—O2 | 51.5 (3) | C9—C11—C12—O1 | −175.2 (2) |
C10—C5—C6—O2 | −175.52 (19) | O1—C12—C13—C15 | −0.4 (3) |
C4—C5—C6—C7 | 168.0 (2) | C11—C12—C13—C15 | −178.6 (3) |
C10—C5—C6—C7 | −59.0 (3) | O1—C12—C13—C14 | −178.0 (2) |
C17—O3—C7—C8 | −26.9 (3) | C11—C12—C13—C14 | 3.8 (5) |
C17—O3—C7—C6 | −148.2 (2) | C12—C13—C14—C17 | −144.8 (3) |
O2—C6—C7—O3 | −66.1 (3) | C15—C13—C14—C17 | 38.5 (5) |
C5—C6—C7—O3 | 174.2 (2) | C12—C13—C14—C8 | −30.8 (3) |
O2—C6—C7—C8 | 177.63 (19) | C15—C13—C14—C8 | 152.5 (3) |
C5—C6—C7—C8 | 57.9 (3) | C7—C8—C14—C13 | −174.3 (2) |
O3—C7—C8—C9 | 173.5 (2) | C9—C8—C14—C13 | 58.8 (3) |
C6—C7—C8—C9 | −61.6 (3) | C7—C8—C14—C17 | −43.3 (2) |
O3—C7—C8—C14 | 43.9 (2) | C9—C8—C14—C17 | −170.2 (2) |
C6—C7—C8—C14 | 168.8 (2) | C12—C13—C15—C16 | 0.1 (3) |
C7—C8—C9—C10 | 59.4 (3) | C14—C13—C15—C16 | 177.0 (3) |
C14—C8—C9—C10 | 179.6 (2) | C13—C15—C16—O1 | 0.2 (4) |
C7—C8—C9—C11 | −173.0 (2) | C12—O1—C16—C15 | −0.5 (3) |
C14—C8—C9—C11 | −52.9 (3) | C7—O3—C17—O4 | −179.6 (3) |
C2—C1—C10—C20 | −69.4 (3) | C7—O3—C17—C14 | −1.4 (3) |
C2—C1—C10—C9 | 171.1 (2) | C13—C14—C17—O4 | −36.2 (5) |
C2—C1—C10—C5 | 54.1 (3) | C8—C14—C17—O4 | −154.1 (3) |
C8—C9—C10—C1 | −173.9 (2) | C13—C14—C17—O3 | 145.9 (2) |
C11—C9—C10—C1 | 63.4 (3) | C8—C14—C17—O3 | 28.0 (3) |
C8—C9—C10—C20 | 67.5 (2) | C6—O2—C21—O5 | 4.7 (4) |
C11—C9—C10—C20 | −55.3 (3) | C6—O2—C21—C22 | −175.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18A···O4i | 0.96 | 2.59 | 3.517 (5) | 162 |
C14—H14A···O5i | 0.98 | 2.54 | 3.450 (4) | 154 |
C3—H3B···O4ii | 0.97 | 2.55 | 3.342 (3) | 138 |
C19—H19A···O1iii | 0.96 | 2.69 | 3.641 (4) | 173 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) x, y−1, z; (iii) −x+3/2, −y+1, z−1/2. |
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