Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702301X/cv2242sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702301X/cv2242Isup2.hkl |
CCDC reference: 651472
The title compound (II) was isolated from aerial parts of Verbesina turbacensis (Asteraceae) in San José, Costa Rica in 2000. Crystals of (II) suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution at room temperature. 1H NMR (400 MHz, DMSO-d6): δ 1.39 (H1a, m), 1.00 (H1b, m), 1.88 (H2a, m), 1.24 (H2b, m), 1.48 (H3a, m), 1.14 (H3b, m), 2.32 (H4, m), 1.55 (H5, dd), 5.42 (H6, dd), 1.14 (H7, m), 1.50 (H8a, m), 1.60 (H8b, m), 1.55 (H9a, m) 1.12 (H9b, m), 1.42 (H11, m), 1.00 (H12, d), 0.81 (H13, d), 1.24 (H14, s), 6.33 (H17, d), 7.62 (H18, d)7.50 (H20–24, m), 7.33 (H21–23, m), 7.33 (H22, m); 13C NMR (100 MHz, DMSO-d6): δ 44.1 (C1, t), 18.6 (C2, t), 29.8 (C3, t), 42.4 (C4, d), 50.4 (C5, d), 74.1 (C6, d), 51.0 (C7, d), 20.7 (C8, d), 44.4 (C9, t), 34.3(C10, s), 28.2 (C11, d), 22.3 (C12, q), 202, (C13, q), 20.6 (C14, q), 166.7 (C16, s), 118.6 (C17, d), 144.1 (C18, d), 134.7 (C19, s), 128.1 (C20–24, d), 128.6 (C21–23, d), 129.7 (C22, d).
All H atom attached to C atoms were positioned geometrically like idealized group and isotropic displacement parameters were set equal to 1.2 times Ueq(parent) or 1.5 Ueq(parent) (methyls). The hydroxy H atom was positioned geometrically [O—H 0.82 Å], and refined with Uiso(H)= 1.2Ueq(O). The absolute configuration was not established because of the absence of significant anomalous scatterers. 915 Friedel pairs were merged before the final refinement.
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# Following replaced by publCIF - lun 23. abr 23:01:28 2007
The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF.
For related literature, see [type here to add references to related ].
Data collection: MSC/AFC Difractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Difractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: PLATON (Spek, 2003).
C24H32O4 | F(000) = 832 |
Mr = 384.50 | Dx = 1.174 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 20 reflections |
a = 14.252 (3) Å | θ = 1.8–24.8° |
b = 17.312 (3) Å | µ = 0.08 mm−1 |
c = 8.820 (4) Å | T = 293 K |
V = 2176.1 (11) Å3 | Rectangular, colourless |
Z = 4 | 0.40 × 0.20 × 0.10 mm |
Rigaku AFC-7S diffractometer | Rint = 0.025 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.9° |
Graphite monochromator | h = −3→10 |
ω–2θ scans | k = −3→20 |
3559 measured reflections | l = −3→10 |
1697 independent reflections | 3 standard reflections every 150 reflections |
1060 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0389P)2 + 0.3391P] where P = (Fo2 + 2Fc2)/3 |
1697 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C24H32O4 | V = 2176.1 (11) Å3 |
Mr = 384.50 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 14.252 (3) Å | µ = 0.08 mm−1 |
b = 17.312 (3) Å | T = 293 K |
c = 8.820 (4) Å | 0.40 × 0.20 × 0.10 mm |
Rigaku AFC-7S diffractometer | Rint = 0.025 |
3559 measured reflections | 3 standard reflections every 150 reflections |
1697 independent reflections | intensity decay: none |
1060 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.11 e Å−3 |
1697 reflections | Δρmin = −0.15 e Å−3 |
253 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1910 (3) | 0.0954 (2) | 0.4197 (4) | 0.078 (1) | |
H1 | 0.2165 | 0.0779 | 0.4956 | 0.117* | |
O2 | 0.1115 (3) | 0.1614 (2) | 0.5900 (4) | 0.0927 (14) | |
O3 | 0.0645 (2) | −0.00138 (16) | 0.2568 (3) | 0.0465 (9) | |
O4 | 0.2036 (2) | −0.02560 (16) | 0.1437 (4) | 0.0560 (10) | |
C1 | −0.1312 (4) | 0.1924 (3) | 0.3740 (7) | 0.0755 (19) | |
H1A | −0.1508 | 0.2205 | 0.2843 | 0.091* | |
H1B | −0.1865 | 0.1835 | 0.4356 | 0.091* | |
C2 | −0.0636 (4) | 0.2423 (3) | 0.4624 (7) | 0.0770 (18) | |
H2A | −0.0488 | 0.2173 | 0.5580 | 0.092* | |
H2B | −0.0929 | 0.2915 | 0.4847 | 0.092* | |
C3 | 0.0262 (4) | 0.2557 (3) | 0.3736 (6) | 0.0727 (18) | |
H3A | 0.0696 | 0.2852 | 0.4354 | 0.087* | |
H3B | 0.0121 | 0.2859 | 0.2839 | 0.087* | |
C4 | 0.0734 (4) | 0.1798 (2) | 0.3256 (6) | 0.0545 (15) | |
H4 | 0.1220 | 0.1939 | 0.2521 | 0.065* | |
C5 | 0.0021 (4) | 0.1291 (2) | 0.2386 (6) | 0.0488 (13) | |
H5 | −0.0183 | 0.1638 | 0.1572 | 0.059* | |
C6 | 0.0416 (3) | 0.0607 (2) | 0.1502 (5) | 0.0435 (13) | |
H6 | 0.0986 | 0.0767 | 0.0964 | 0.052* | |
C7 | −0.0299 (3) | 0.0289 (3) | 0.0360 (5) | 0.0507 (13) | |
H7 | −0.0456 | 0.0716 | −0.0323 | 0.061* | |
C8 | −0.1198 (4) | 0.0090 (3) | 0.1220 (6) | 0.0691 (16) | |
H8A | −0.1667 | −0.0087 | 0.0502 | 0.083* | |
H8B | −0.1070 | −0.0331 | 0.1915 | 0.083* | |
C9 | −0.1592 (4) | 0.0771 (4) | 0.2109 (6) | 0.0789 (18) | |
H9A | −0.2146 | 0.0599 | 0.2654 | 0.095* | |
H9B | −0.1790 | 0.1165 | 0.1396 | 0.095* | |
C10 | −0.0909 (4) | 0.1135 (3) | 0.3245 (6) | 0.0573 (15) | |
C11 | 0.0080 (4) | −0.0369 (3) | −0.0645 (6) | 0.0602 (15) | |
H11 | 0.0342 | −0.0768 | 0.0021 | 0.072* | |
C12 | −0.0695 (4) | −0.0744 (3) | −0.1611 (6) | 0.093 (2) | |
H12A | −0.1191 | −0.0922 | −0.0962 | 0.139* | |
H12B | −0.0439 | −0.1173 | −0.2164 | 0.139* | |
H12C | −0.0940 | −0.0370 | −0.2311 | 0.139* | |
C13 | 0.0865 (4) | −0.0087 (3) | −0.1692 (5) | 0.0769 (17) | |
H13A | 0.1097 | −0.0512 | −0.2282 | 0.115* | |
H13B | 0.1367 | 0.0123 | −0.1093 | 0.115* | |
H13C | 0.0625 | 0.0305 | −0.2356 | 0.115* | |
C14 | −0.0817 (3) | 0.0609 (3) | 0.4648 (5) | 0.0715 (17) | |
H14A | −0.0556 | 0.0121 | 0.4351 | 0.107* | |
H14B | −0.1426 | 0.0529 | 0.5087 | 0.107* | |
H14C | −0.0413 | 0.0850 | 0.5379 | 0.107* | |
C15 | 0.1245 (4) | 0.1448 (3) | 0.4604 (7) | 0.0604 (15) | |
C16 | 0.1471 (4) | −0.0392 (3) | 0.2424 (6) | 0.0440 (13) | |
C17 | 0.1552 (3) | −0.0980 (2) | 0.3611 (5) | 0.0480 (13) | |
H17 | 0.1090 | −0.1019 | 0.4351 | 0.058* | |
C18 | 0.2278 (4) | −0.1457 (2) | 0.3642 (5) | 0.0501 (14) | |
H18 | 0.2742 | −0.1373 | 0.2918 | 0.060* | |
C19 | 0.2432 (4) | −0.2099 (2) | 0.4681 (6) | 0.0481 (13) | |
C20 | 0.1829 (4) | −0.2284 (3) | 0.5827 (6) | 0.0736 (17) | |
H20 | 0.1304 | −0.1977 | 0.6002 | 0.088* | |
C21 | 0.1989 (5) | −0.2928 (3) | 0.6737 (6) | 0.087 (2) | |
H21 | 0.1574 | −0.3048 | 0.7516 | 0.105* | |
C22 | 0.2754 (5) | −0.3382 (3) | 0.6487 (7) | 0.080 (2) | |
H22 | 0.2856 | −0.3815 | 0.7087 | 0.096* | |
C23 | 0.3363 (4) | −0.3203 (3) | 0.5370 (7) | 0.0721 (17) | |
H23 | 0.3885 | −0.3515 | 0.5209 | 0.086* | |
C24 | 0.3221 (4) | −0.2563 (3) | 0.4465 (6) | 0.0582 (15) | |
H24 | 0.3651 | −0.2442 | 0.3709 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.079 (3) | 0.081 (2) | 0.073 (3) | 0.030 (2) | −0.018 (2) | −0.011 (2) |
O2 | 0.089 (3) | 0.125 (3) | 0.063 (2) | 0.037 (3) | −0.007 (3) | −0.015 (3) |
O3 | 0.039 (2) | 0.0480 (17) | 0.0520 (19) | 0.0044 (18) | −0.0016 (19) | 0.0176 (17) |
O4 | 0.048 (3) | 0.059 (2) | 0.061 (2) | 0.0099 (18) | 0.007 (2) | 0.0085 (19) |
C1 | 0.068 (5) | 0.078 (4) | 0.081 (4) | 0.031 (4) | 0.019 (4) | 0.022 (3) |
C2 | 0.080 (5) | 0.063 (3) | 0.088 (4) | 0.030 (3) | 0.023 (4) | 0.000 (4) |
C3 | 0.081 (5) | 0.049 (3) | 0.089 (4) | 0.015 (3) | 0.013 (4) | 0.007 (3) |
C4 | 0.061 (4) | 0.045 (3) | 0.057 (3) | 0.008 (3) | 0.006 (3) | 0.014 (3) |
C5 | 0.043 (4) | 0.047 (3) | 0.056 (3) | 0.008 (3) | −0.001 (3) | 0.020 (3) |
C6 | 0.035 (3) | 0.046 (3) | 0.049 (3) | −0.001 (2) | −0.006 (3) | 0.017 (3) |
C7 | 0.037 (4) | 0.060 (3) | 0.055 (3) | −0.008 (3) | −0.013 (3) | 0.019 (3) |
C8 | 0.040 (4) | 0.088 (4) | 0.079 (4) | −0.012 (3) | −0.014 (3) | 0.012 (4) |
C9 | 0.044 (5) | 0.110 (5) | 0.083 (4) | 0.006 (4) | −0.001 (4) | 0.023 (4) |
C10 | 0.035 (4) | 0.071 (3) | 0.065 (3) | 0.012 (3) | 0.004 (4) | 0.019 (3) |
C11 | 0.063 (4) | 0.059 (3) | 0.058 (3) | −0.009 (3) | −0.010 (3) | 0.005 (3) |
C12 | 0.093 (5) | 0.104 (4) | 0.081 (4) | −0.030 (4) | −0.029 (4) | −0.005 (4) |
C13 | 0.079 (5) | 0.090 (4) | 0.062 (3) | −0.013 (4) | 0.001 (4) | 0.003 (3) |
C14 | 0.065 (4) | 0.079 (3) | 0.070 (3) | 0.001 (3) | 0.019 (4) | 0.031 (3) |
C15 | 0.056 (5) | 0.054 (3) | 0.071 (4) | −0.002 (3) | 0.001 (4) | −0.004 (3) |
C16 | 0.034 (4) | 0.041 (3) | 0.057 (3) | 0.000 (3) | −0.008 (3) | −0.008 (3) |
C17 | 0.048 (4) | 0.041 (3) | 0.055 (3) | 0.003 (3) | −0.001 (3) | 0.010 (3) |
C18 | 0.059 (4) | 0.042 (3) | 0.049 (3) | 0.001 (3) | −0.006 (3) | −0.006 (3) |
C19 | 0.055 (4) | 0.044 (3) | 0.045 (3) | 0.010 (3) | −0.016 (3) | −0.006 (3) |
C20 | 0.092 (5) | 0.066 (3) | 0.063 (4) | 0.030 (3) | 0.013 (4) | 0.012 (3) |
C21 | 0.112 (6) | 0.087 (4) | 0.062 (4) | 0.029 (4) | 0.018 (4) | 0.026 (4) |
C22 | 0.112 (6) | 0.060 (3) | 0.068 (4) | 0.016 (4) | −0.020 (4) | 0.013 (4) |
C23 | 0.077 (5) | 0.059 (3) | 0.080 (4) | 0.021 (3) | −0.028 (4) | 0.001 (4) |
C24 | 0.059 (4) | 0.058 (3) | 0.058 (3) | 0.004 (3) | −0.012 (3) | −0.001 (3) |
O1—C15 | 1.326 (6) | C9—H9A | 0.9700 |
O1—H1 | 0.8200 | C9—H9B | 0.9700 |
O2—C15 | 1.194 (6) | C10—C14 | 1.542 (6) |
O3—C16 | 1.353 (5) | C11—C13 | 1.531 (6) |
O3—C6 | 1.465 (4) | C11—C12 | 1.539 (6) |
O4—C16 | 1.209 (5) | C11—H11 | 0.9800 |
C1—C2 | 1.510 (7) | C12—H12A | 0.9600 |
C1—C10 | 1.545 (6) | C12—H12B | 0.9600 |
C1—H1A | 0.9700 | C12—H12C | 0.9600 |
C1—H1B | 0.9700 | C13—H13A | 0.9600 |
C2—C3 | 1.519 (7) | C13—H13B | 0.9600 |
C2—H2A | 0.9700 | C13—H13C | 0.9600 |
C2—H2B | 0.9700 | C14—H14A | 0.9600 |
C3—C4 | 1.535 (6) | C14—H14B | 0.9600 |
C3—H3A | 0.9700 | C14—H14C | 0.9600 |
C3—H3B | 0.9700 | C16—C17 | 1.465 (6) |
C4—C15 | 1.521 (7) | C17—C18 | 1.324 (6) |
C4—C5 | 1.546 (6) | C17—H17 | 0.9300 |
C4—H4 | 0.9800 | C18—C19 | 1.457 (6) |
C5—C6 | 1.526 (6) | C18—H18 | 0.9300 |
C5—C10 | 1.550 (6) | C19—C20 | 1.366 (6) |
C5—H5 | 0.9800 | C19—C24 | 1.395 (6) |
C6—C7 | 1.535 (6) | C20—C21 | 1.393 (7) |
C6—H6 | 0.9800 | C20—H20 | 0.9300 |
C7—C8 | 1.527 (6) | C21—C22 | 1.361 (7) |
C7—C11 | 1.542 (6) | C21—H21 | 0.9300 |
C7—H7 | 0.9800 | C22—C23 | 1.349 (7) |
C8—C9 | 1.523 (6) | C22—H22 | 0.9300 |
C8—H8A | 0.9700 | C23—C24 | 1.381 (6) |
C8—H8B | 0.9700 | C23—H23 | 0.9300 |
C9—C10 | 1.533 (7) | C24—H24 | 0.9300 |
C15—O1—H1 | 109.5 | C14—C10—C1 | 109.0 (4) |
C16—O3—C6 | 119.2 (4) | C9—C10—C5 | 107.2 (4) |
C2—C1—C10 | 114.5 (5) | C14—C10—C5 | 115.0 (4) |
C2—C1—H1A | 108.6 | C1—C10—C5 | 107.5 (4) |
C10—C1—H1A | 108.6 | C13—C11—C12 | 109.0 (4) |
C2—C1—H1B | 108.6 | C13—C11—C7 | 111.5 (4) |
C10—C1—H1B | 108.6 | C12—C11—C7 | 112.2 (4) |
H1A—C1—H1B | 107.6 | C13—C11—H11 | 108.0 |
C1—C2—C3 | 111.0 (5) | C12—C11—H11 | 108.0 |
C1—C2—H2A | 109.4 | C7—C11—H11 | 108.0 |
C3—C2—H2A | 109.4 | C11—C12—H12A | 109.5 |
C1—C2—H2B | 109.4 | C11—C12—H12B | 109.5 |
C3—C2—H2B | 109.4 | H12A—C12—H12B | 109.5 |
H2A—C2—H2B | 108.0 | C11—C12—H12C | 109.5 |
C2—C3—C4 | 112.3 (4) | H12A—C12—H12C | 109.5 |
C2—C3—H3A | 109.1 | H12B—C12—H12C | 109.5 |
C4—C3—H3A | 109.1 | C11—C13—H13A | 109.5 |
C2—C3—H3B | 109.1 | C11—C13—H13B | 109.5 |
C4—C3—H3B | 109.1 | H13A—C13—H13B | 109.5 |
H3A—C3—H3B | 107.9 | C11—C13—H13C | 109.5 |
C15—C4—C3 | 109.6 (5) | H13A—C13—H13C | 109.5 |
C15—C4—C5 | 118.5 (4) | H13B—C13—H13C | 109.5 |
C3—C4—C5 | 109.6 (4) | C10—C14—H14A | 109.5 |
C15—C4—H4 | 106.1 | C10—C14—H14B | 109.5 |
C3—C4—H4 | 106.1 | H14A—C14—H14B | 109.5 |
C5—C4—H4 | 106.1 | C10—C14—H14C | 109.5 |
C6—C5—C4 | 116.8 (4) | H14A—C14—H14C | 109.5 |
C6—C5—C10 | 115.4 (4) | H14B—C14—H14C | 109.5 |
C4—C5—C10 | 114.7 (4) | O2—C15—O1 | 121.7 (5) |
C6—C5—H5 | 102.2 | O2—C15—C4 | 125.4 (5) |
C4—C5—H5 | 102.2 | O1—C15—C4 | 112.8 (5) |
C10—C5—H5 | 102.2 | O4—C16—O3 | 123.5 (4) |
O3—C6—C5 | 108.9 (3) | O4—C16—C17 | 126.7 (5) |
O3—C6—C7 | 107.8 (3) | O3—C16—C17 | 109.8 (5) |
C5—C6—C7 | 111.6 (4) | C18—C17—C16 | 120.6 (5) |
O3—C6—H6 | 109.5 | C18—C17—H17 | 119.7 |
C5—C6—H6 | 109.5 | C16—C17—H17 | 119.7 |
C7—C6—H6 | 109.5 | C17—C18—C19 | 127.3 (5) |
C8—C7—C6 | 108.2 (4) | C17—C18—H18 | 116.3 |
C8—C7—C11 | 114.4 (4) | C19—C18—H18 | 116.3 |
C6—C7—C11 | 114.2 (4) | C20—C19—C24 | 118.2 (5) |
C8—C7—H7 | 106.5 | C20—C19—C18 | 123.3 (5) |
C6—C7—H7 | 106.5 | C24—C19—C18 | 118.4 (5) |
C11—C7—H7 | 106.5 | C19—C20—C21 | 120.7 (5) |
C9—C8—C7 | 113.0 (4) | C19—C20—H20 | 119.6 |
C9—C8—H8A | 109.0 | C21—C20—H20 | 119.6 |
C7—C8—H8A | 109.0 | C22—C21—C20 | 120.0 (6) |
C9—C8—H8B | 109.0 | C22—C21—H21 | 120.0 |
C7—C8—H8B | 109.0 | C20—C21—H21 | 120.0 |
H8A—C8—H8B | 107.8 | C23—C22—C21 | 120.1 (5) |
C8—C9—C10 | 114.8 (4) | C23—C22—H22 | 119.9 |
C8—C9—H9A | 108.6 | C21—C22—H22 | 119.9 |
C10—C9—H9A | 108.6 | C22—C23—C24 | 120.7 (6) |
C8—C9—H9B | 108.6 | C22—C23—H23 | 119.6 |
C10—C9—H9B | 108.6 | C24—C23—H23 | 119.6 |
H9A—C9—H9B | 107.5 | C23—C24—C19 | 120.2 (5) |
C9—C10—C14 | 109.6 (4) | C23—C24—H24 | 119.9 |
C9—C10—C1 | 108.2 (5) | C19—C24—H24 | 119.9 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4i | 0.82 | 1.96 | 2.760 (5) | 167 |
Symmetry code: (i) −x+1/2, −y, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C24H32O4 |
Mr | 384.50 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 14.252 (3), 17.312 (3), 8.820 (4) |
V (Å3) | 2176.1 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.40 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Rigaku AFC-7S |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3559, 1697, 1060 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.098, 1.01 |
No. of reflections | 1697 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.11, −0.15 |
Computer programs: MSC/AFC Difractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Difractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 2001), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4i | 0.82 | 1.96 | 2.760 (5) | 167.1 |
Symmetry code: (i) −x+1/2, −y, z+1/2. |
Sesquiterpene derivatives are natural products responsible for the anti-inflammatory activity of a variety of medicinal plants, mainly from the Asteraceae family (Castro et al., 2000; Amaro-Luis et al., 2002; Wagner et al., 2004; Stefani et al., 2006). In particular, from the Verbesina turbacensis plant, collected in Costa Rica, were isolated the sesquiterpenes 15 ol derivate and the 15 oic derivate (I). The title compound (I), was reported in its esther's form, extracted from the Verbesina eggersii collected in Ecuador (Bohlmann & Lonitz, 1978) and later from Verbesina turbacensis collected in Venezuela (Amaro-Luis et al., 2002). In the molecule, all bond lengths and angles are normal. The molecular structure of (I) (Fig. 1) shows that the A and B rings adopt the chair conformations [ΔC2(2–3)min = 1.7 (6), ΔC2(3–4)max = 2.6 (6), ΔCs(2)min = 1.1 (4), ΔCs(1)max = 2.3 (5)] for A and [ΔC2(6–7))min = 3.9 (6), ΔC2(5–6))max = 5.2 (6), ΔCs(7)min = 0.5 (5), ΔCs(6)max = 4.6 (5)] for B, respectively [Griffin, J. F., Duax, W. & Weeks, M. (1984). "Atlas of Steroid Structure". New York: Plenum Publishing corporation]. The crystal packing is stabilized by an O—H···O hydrogen bond (Table 1). In the extended zigzag chains which run along the [001] direction, as depicted in Fig. 2, molecules are related by 21 screw axis, and are linked by hydrogen bonds; each molecule acting as a donor of a hydrogen atom through the carboxylic acid group, and as an acceptor of a hydrogen atom through the oxygen atom in the esther group. Hydrophobic groups are located in the outer region of each chain.