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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.045
- wR factor = 0.098
- Data-to-parameter ratio = 6.7
checkCIF/PLATON results
No syntax errors found
Alert level A REFLT03_ALERT_1_A Reflection count < 85% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 24.99 From the CIF: _diffrn_reflns_theta_full 24.99 From the CIF: _reflns_number_total 1697 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2195 Completeness (_total/calc) 77.31%
Author Response: The data collection was performed in 2000, and the Rigaku instrument used in that moment does not physically allow a full coverage of the high angle data. |
PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.77
Author Response: The data collection was performed in 2000, and the Rigaku instrument used in that moment does not physically allow a full coverage of the high angle data. |
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.77
Author Response: The data collection was performed in 2000, and the Rigaku instrument used in that moment does not physically allow a full coverage of the high angle data. |
Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg.
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.71 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 24.99 From the CIF: _reflns_number_total 1697 From the CIF: _diffrn_reflns_limit_ max hkl 10. 20. 10. From the CIF: _diffrn_reflns_limit_ min hkl -3. -3. -3. TEST1: Expected hkl limits for theta max Calculated maximum hkl 16. 20. 10. Calculated minimum hkl -16. -20. -10.
Author Response: The data collection was performed in 2000, and the Rigaku instrument used in that moment does not physically allow a full coverage of the high angle data. |
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 24.99 From the CIF: _reflns_number_total 1697 Count of symmetry unique reflns 2195 Completeness (_total/calc) 77.31% 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
Author Response: The data collection was performed in 2000, and the Rigaku instrument used in that moment does not physically allow a full coverage of the high angle data. |
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S
3 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 9 ALERT level G = General alerts; check 9 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 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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.