Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053317/dn2250sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053317/dn2250Isup2.hkl |
CCDC reference: 667487
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.038
- wR factor = 0.095
- Data-to-parameter ratio = 7.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.49 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.54 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C22 H28 O8
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 25.01 From the CIF: _reflns_number_total 4122 Count of symmetry unique reflns 4124 Completeness (_total/calc) 99.95% 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 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 C1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19A = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 21 ALERT level G = General alerts; check 21 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Cremer & Pople (1975); Shi et al. (2003, 2007); Spek (2003).
Macrocalyxin J (200 mg; isolated from Rabdosia macrocalyx) was reacted with NaBH4 in 2-propanol and compound (II) was gained, 1H NMR (C5D5N, 400 MHz): 0.94,0.97(2× 3H,s), 1.24(3H,d, J=7 Hz),2.76(1H,s), 2.09(3H,s), 3.04(1H,d,J=4 Hz), 2.24(1H,m,13-H), 4.35,4.52(2×1H,d,AB, J=9 Hz), 5.99(1H,m), 3.09(H,q, J=7 Hz), 5.14(1H,m),5.78(1H,s), 13C NMR (C5D5N, 100 MHz): 11.1 (CH3), 21.3 (CH3), 23.5(CH3), 24.2(CH2), 31.7(C), 31.7(CH2), 33.3(CH3), 37.4(CH2), 38.3(CH), 44.9(CH), 50.1(C), 52.3(CH), 55.8(CH), 61.5(C), 65.2(CH), 74.4(CH2), 75.3(CH), 78.5(CH), 102.0(CH), 168.2(C), 170.5(C), 213.7(C). The compound (II) was then reacted with Jones reagent in acetone, compound (I) was gained as a white residue. Recrystallization with methanol gave the title compound (I) as colorless crystals, 1H NMR (CDCl3, 400 MHz): 1.06,1.22(2×3H,s,2× Me), 1.15(3H,d, J=7 Hz), 2.69(1H,s,5-H), 2.06(3H,s, OAc), 3.05(H,q, J=7 Hz), 3.99,4.33(2×1H,d, J=10 Hz), 4.19(1H,brs), 6.71(1H,d, J=2 Hz, 14-H), 5.23(1H,dd,J=6,12 Hz).
Crystals suitable for X-ray structure analysis were obtained by slow evaporation from a solution of methanol at room temperature.
H atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.96 Å (CH3), 0.97 Å (CH2) and 0.98(CH) and with the temperature factors Uiso= 1.5 Ueq(CH3) and 1.2 Ueq(CH2, CH).
In the absence of significant anomalous scattering, the absolute configuration could not be reliably determined from the X-ray analyses and then the Friedel pairs were merged and any references to the Flack parameter were removed.
Since the natural diterpenoid Macrocalyxin J exhibits cytotoxicity in vitro against cultures of Hela cells (Shi et al., 2007), we have derived the title compound from it.
Two unique molecules are present in the asymmetric unit, both molecule I (Fig.1) and molecule II (Fig.2) are built up from five fused rings, three six membered (A,B,C,A',B'and C') and two five membered rings (D,E,D' and E'). This two molecules are linked by a O—H···O hydrogen bond to form a pseudo dimer. The dimer are further interconnected through O—H···O hydrogen bonds to build up a chain parallel to the a axis (Table 1, Fig.3).
The conformations of the different rings extracted from the puckering parameters (Cremer & Pople, 1975) are given in Table 2. Ring A and A' adopt a chair conformation, ring B and B' exist in a screw-boat conformation and rings C and C' adopt a boat conformation. Rings D and D' present a twist conformation whereas rings E and E' adopt an envelope conformation.
Since the title compound was prepared from Macrocalyxin J, which was isolated from the same plant (i.e. Rabdosia macrocalyx) as Macrocalyxin A, the configuration can be deduced from the known chirality of the Macrocalyxin A (Shi et al., 2003),and thus Fig. 1 and Fig. 2 represents the correct absolute configuration.
For related literature, see: Cremer & Pople (1975); Shi et al. (2003, 2007); Spek (2003).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C22H28O8 | F(000) = 1792 |
Mr = 420.44 | Dx = 1.339 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5045 reflections |
a = 11.9500 (11) Å | θ = 2.2–21.9° |
b = 13.7531 (16) Å | µ = 0.10 mm−1 |
c = 25.377 (3) Å | T = 293 K |
V = 4170.7 (8) Å3 | Plate, colorless |
Z = 8 | 0.50 × 0.46 × 0.27 mm |
Bruker SMART CCD area-detector diffractometer | 4122 independent reflections |
Radiation source: fine-focus sealed tube | 2948 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −14→13 |
Tmin = 0.951, Tmax = 0.973 | k = −16→6 |
20027 measured reflections | l = −29→30 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0342P)2 + 1.1127P] where P = (Fo2 + 2Fc2)/3 |
4122 reflections | (Δ/σ)max = 0.001 |
550 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C22H28O8 | V = 4170.7 (8) Å3 |
Mr = 420.44 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 11.9500 (11) Å | µ = 0.10 mm−1 |
b = 13.7531 (16) Å | T = 293 K |
c = 25.377 (3) Å | 0.50 × 0.46 × 0.27 mm |
Bruker SMART CCD area-detector diffractometer | 4122 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 2948 reflections with I > 2σ(I) |
Tmin = 0.951, Tmax = 0.973 | Rint = 0.051 |
20027 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.19 e Å−3 |
4122 reflections | Δρmin = −0.17 e Å−3 |
550 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 | −0.0926 (2) | 0.9061 (2) | 0.15436 (10) | 0.0632 (8) | |
O2 | 0.0368 (3) | 0.4543 (2) | 0.03746 (12) | 0.0792 (10) | |
O3 | 0.0107 (2) | 0.78491 (18) | 0.18023 (9) | 0.0483 (6) | |
O4 | 0.27213 (19) | 0.74065 (19) | 0.08031 (9) | 0.0495 (6) | |
H4 | 0.3334 | 0.7412 | 0.0658 | 0.074* | |
O5 | −0.1385 (2) | 0.8632 (2) | 0.04103 (12) | 0.0623 (8) | |
O6 | 0.1031 (2) | 1.00999 (17) | 0.10644 (9) | 0.0482 (6) | |
O7 | 0.1783 (3) | 0.9770 (3) | 0.18505 (11) | 0.0803 (10) | |
O10 | −0.0762 (2) | 0.5583 (2) | 0.07852 (10) | 0.0585 (7) | |
O1A | 0.4834 (3) | 1.3128 (2) | 0.15642 (12) | 0.0773 (9) | |
O2A | 0.4943 (2) | 0.8266 (2) | 0.05435 (10) | 0.0567 (7) | |
O3A | 0.5169 (2) | 1.1686 (2) | 0.18999 (10) | 0.0598 (8) | |
O4A | 0.7978 (2) | 1.06592 (19) | 0.12314 (11) | 0.0609 (7) | |
H4A | 0.8319 | 1.0142 | 0.1233 | 0.091* | |
O5A | 0.4647 (3) | 1.2672 (3) | 0.04184 (13) | 0.0871 (11) | |
O6A | 0.7140 (2) | 1.35784 (18) | 0.12540 (10) | 0.0546 (7) | |
O7A | 0.7396 (3) | 1.3172 (3) | 0.20922 (13) | 0.0962 (12) | |
O10A | 0.4091 (2) | 0.9613 (2) | 0.08057 (9) | 0.0508 (7) | |
C1 | 0.0354 (3) | 0.8444 (2) | 0.09003 (12) | 0.0372 (8) | |
C2 | −0.0205 (3) | 0.8474 (3) | 0.14339 (14) | 0.0434 (9) | |
C4 | 0.0956 (3) | 0.7135 (2) | 0.16609 (13) | 0.0399 (8) | |
H4B | 0.1670 | 0.7468 | 0.1602 | 0.048* | |
C5 | 0.1073 (4) | 0.6453 (3) | 0.21185 (14) | 0.0541 (10) | |
H5A | 0.0350 | 0.6180 | 0.2209 | 0.065* | |
H5B | 0.1360 | 0.6798 | 0.2423 | 0.065* | |
C6 | 0.1878 (4) | 0.5645 (3) | 0.19610 (15) | 0.0587 (11) | |
H6A | 0.2028 | 0.5241 | 0.2266 | 0.070* | |
H6B | 0.2581 | 0.5933 | 0.1850 | 0.070* | |
C7 | 0.1427 (3) | 0.5001 (3) | 0.15139 (15) | 0.0523 (10) | |
C8 | 0.1136 (3) | 0.5667 (2) | 0.10297 (13) | 0.0416 (9) | |
H8 | 0.1816 | 0.5776 | 0.0822 | 0.050* | |
C9 | 0.0268 (4) | 0.5191 (3) | 0.06858 (15) | 0.0547 (10) | |
C11 | −0.0660 (3) | 0.6361 (3) | 0.11584 (15) | 0.0470 (9) | |
H11A | −0.0876 | 0.6145 | 0.1508 | 0.056* | |
H11B | −0.1132 | 0.6904 | 0.1058 | 0.056* | |
C12 | 0.0580 (3) | 0.6658 (2) | 0.11490 (13) | 0.0359 (8) | |
C13 | 0.0721 (3) | 0.7405 (2) | 0.06980 (12) | 0.0339 (8) | |
H13 | 0.0169 | 0.7222 | 0.0430 | 0.041* | |
C14 | 0.1855 (3) | 0.7421 (3) | 0.04123 (13) | 0.0416 (9) | |
H14 | 0.1917 | 0.6830 | 0.0199 | 0.050* | |
C15 | 0.1962 (3) | 0.8300 (3) | 0.00484 (13) | 0.0468 (9) | |
H15A | 0.1584 | 0.8154 | −0.0280 | 0.056* | |
H15B | 0.2748 | 0.8398 | −0.0031 | 0.056* | |
C16 | 0.1483 (3) | 0.9253 (3) | 0.02698 (13) | 0.0422 (9) | |
H16 | 0.1976 | 0.9800 | 0.0184 | 0.051* | |
C17 | 0.0278 (3) | 0.9473 (3) | 0.00972 (13) | 0.0456 (9) | |
H17 | 0.0131 | 1.0147 | 0.0201 | 0.055* | |
C18 | −0.0415 (3) | 0.8848 (3) | 0.04604 (14) | 0.0443 (9) | |
C19 | 0.1352 (3) | 0.9156 (2) | 0.08652 (13) | 0.0386 (8) | |
H19 | 0.2028 | 0.8902 | 0.1036 | 0.046* | |
C20 | −0.0037 (4) | 0.9399 (3) | −0.04832 (14) | 0.0694 (13) | |
H20A | 0.0026 | 0.8735 | −0.0596 | 0.104* | |
H20B | 0.0459 | 0.9798 | −0.0688 | 0.104* | |
H20C | −0.0793 | 0.9617 | −0.0531 | 0.104* | |
C21 | 0.2364 (4) | 0.4304 (3) | 0.13425 (17) | 0.0732 (13) | |
H21A | 0.3021 | 0.4671 | 0.1254 | 0.110* | |
H21B | 0.2123 | 0.3939 | 0.1041 | 0.110* | |
H21C | 0.2533 | 0.3865 | 0.1626 | 0.110* | |
C22 | 0.0444 (4) | 0.4386 (3) | 0.17108 (18) | 0.0718 (13) | |
H22A | 0.0685 | 0.3990 | 0.2001 | 0.108* | |
H22B | 0.0180 | 0.3978 | 0.1430 | 0.108* | |
H22C | −0.0150 | 0.4807 | 0.1825 | 0.108* | |
C23 | 0.1316 (4) | 1.0317 (3) | 0.15682 (15) | 0.0542 (11) | |
C24 | 0.0941 (5) | 1.1328 (3) | 0.17004 (17) | 0.0873 (17) | |
H24A | 0.1209 | 1.1501 | 0.2044 | 0.131* | |
H24B | 0.0138 | 1.1356 | 0.1697 | 0.131* | |
H24C | 0.1234 | 1.1775 | 0.1445 | 0.131* | |
C1A | 0.6037 (3) | 1.2117 (3) | 0.10504 (13) | 0.0409 (8) | |
C2A | 0.5294 (3) | 1.2360 (3) | 0.15192 (15) | 0.0523 (10) | |
C4A | 0.5786 (3) | 1.0783 (3) | 0.18451 (13) | 0.0487 (10) | |
H4C | 0.6589 | 1.0925 | 0.1865 | 0.058* | |
C5A | 0.5476 (4) | 1.0122 (3) | 0.22930 (13) | 0.0652 (13) | |
H5C | 0.4672 | 1.0032 | 0.2302 | 0.078* | |
H5D | 0.5706 | 1.0411 | 0.2625 | 0.078* | |
C6A | 0.6053 (4) | 0.9150 (3) | 0.22193 (14) | 0.0670 (13) | |
H6C | 0.5931 | 0.8754 | 0.2531 | 0.080* | |
H6D | 0.6852 | 0.9255 | 0.2184 | 0.080* | |
C7A | 0.5632 (3) | 0.8600 (3) | 0.17376 (15) | 0.0521 (10) | |
C8A | 0.5778 (3) | 0.9269 (3) | 0.12381 (12) | 0.0397 (8) | |
H8A | 0.6536 | 0.9189 | 0.1098 | 0.048* | |
C9A | 0.4942 (3) | 0.8973 (3) | 0.08245 (14) | 0.0437 (9) | |
C11A | 0.4270 (3) | 1.0396 (3) | 0.11786 (14) | 0.0493 (10) | |
H11C | 0.3830 | 1.0295 | 0.1495 | 0.059* | |
H11D | 0.4066 | 1.1017 | 0.1025 | 0.059* | |
C12A | 0.5527 (3) | 1.0366 (3) | 0.13045 (12) | 0.0386 (8) | |
C13A | 0.6129 (3) | 1.1009 (2) | 0.08914 (12) | 0.0359 (8) | |
H13A | 0.5704 | 1.0937 | 0.0563 | 0.043* | |
C14A | 0.7340 (3) | 1.0734 (3) | 0.07577 (14) | 0.0461 (9) | |
H14A | 0.7339 | 1.0099 | 0.0582 | 0.055* | |
C15A | 0.7862 (4) | 1.1474 (3) | 0.03890 (16) | 0.0569 (11) | |
H15C | 0.7593 | 1.1352 | 0.0034 | 0.068* | |
H15D | 0.8666 | 1.1380 | 0.0388 | 0.068* | |
C16A | 0.7611 (3) | 1.2542 (3) | 0.05332 (15) | 0.0524 (10) | |
H16A | 0.8280 | 1.2945 | 0.0487 | 0.063* | |
C17A | 0.6619 (4) | 1.2986 (3) | 0.02463 (15) | 0.0620 (12) | |
H17A | 0.6661 | 1.3689 | 0.0304 | 0.074* | |
C18A | 0.5612 (4) | 1.2629 (3) | 0.05495 (15) | 0.0545 (11) | |
C19A | 0.7221 (3) | 1.2568 (3) | 0.11028 (14) | 0.0445 (9) | |
H19A | 0.7708 | 1.2193 | 0.1338 | 0.053* | |
C20A | 0.6506 (5) | 1.2834 (4) | −0.03485 (17) | 0.0914 (18) | |
H20D | 0.6298 | 1.2172 | −0.0418 | 0.137* | |
H20E | 0.7208 | 1.2973 | −0.0516 | 0.137* | |
H20F | 0.5941 | 1.3262 | −0.0485 | 0.137* | |
C21A | 0.6354 (4) | 0.7688 (3) | 0.16527 (19) | 0.0782 (14) | |
H21D | 0.7128 | 0.7872 | 0.1631 | 0.117* | |
H21E | 0.6135 | 0.7374 | 0.1331 | 0.117* | |
H21F | 0.6251 | 0.7249 | 0.1943 | 0.117* | |
C22A | 0.4420 (4) | 0.8259 (4) | 0.18302 (16) | 0.0721 (14) | |
H22D | 0.4378 | 0.7910 | 0.2157 | 0.108* | |
H22E | 0.4194 | 0.7840 | 0.1547 | 0.108* | |
H22F | 0.3933 | 0.8813 | 0.1844 | 0.108* | |
C23A | 0.7245 (4) | 1.3779 (3) | 0.17677 (17) | 0.0605 (11) | |
C24A | 0.7089 (4) | 1.4837 (3) | 0.18666 (17) | 0.0733 (14) | |
H24D | 0.6305 | 1.4983 | 0.1881 | 0.110* | |
H24E | 0.7430 | 1.5202 | 0.1587 | 0.110* | |
H24F | 0.7433 | 1.5008 | 0.2196 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0655 (18) | 0.0564 (17) | 0.0676 (17) | 0.0286 (16) | 0.0207 (15) | 0.0124 (15) |
O2 | 0.112 (3) | 0.0530 (18) | 0.0722 (19) | 0.0032 (19) | −0.0168 (19) | −0.0168 (17) |
O3 | 0.0573 (16) | 0.0443 (14) | 0.0434 (13) | 0.0148 (13) | 0.0081 (12) | 0.0071 (13) |
O4 | 0.0304 (12) | 0.0618 (17) | 0.0562 (14) | 0.0032 (13) | −0.0017 (11) | 0.0044 (14) |
O5 | 0.0391 (16) | 0.0651 (19) | 0.083 (2) | 0.0028 (14) | −0.0143 (14) | 0.0105 (16) |
O6 | 0.0636 (17) | 0.0387 (15) | 0.0424 (14) | 0.0013 (13) | −0.0037 (13) | −0.0006 (12) |
O7 | 0.095 (2) | 0.096 (2) | 0.0492 (17) | 0.013 (2) | −0.0199 (17) | −0.0014 (18) |
O10 | 0.0553 (18) | 0.0510 (17) | 0.0692 (17) | −0.0096 (15) | −0.0172 (15) | 0.0004 (15) |
O1A | 0.076 (2) | 0.073 (2) | 0.083 (2) | 0.0269 (19) | 0.0140 (17) | −0.0199 (18) |
O2A | 0.0623 (18) | 0.0582 (17) | 0.0494 (15) | −0.0120 (15) | 0.0006 (14) | −0.0097 (15) |
O3A | 0.0631 (18) | 0.0687 (19) | 0.0477 (15) | −0.0078 (16) | 0.0164 (14) | −0.0128 (15) |
O4A | 0.0511 (16) | 0.0486 (16) | 0.0830 (19) | 0.0128 (14) | −0.0104 (15) | 0.0132 (16) |
O5A | 0.079 (2) | 0.097 (3) | 0.086 (2) | 0.037 (2) | −0.0359 (19) | 0.005 (2) |
O6A | 0.0729 (19) | 0.0415 (15) | 0.0494 (16) | 0.0006 (14) | −0.0010 (14) | −0.0018 (13) |
O7A | 0.140 (3) | 0.087 (3) | 0.0612 (19) | −0.003 (2) | −0.020 (2) | 0.006 (2) |
O10A | 0.0396 (15) | 0.0643 (17) | 0.0486 (14) | −0.0070 (14) | −0.0077 (12) | −0.0090 (14) |
C1 | 0.0352 (19) | 0.0392 (19) | 0.0372 (18) | 0.0036 (17) | −0.0021 (15) | 0.0062 (16) |
C2 | 0.044 (2) | 0.038 (2) | 0.049 (2) | 0.0052 (19) | 0.0031 (18) | 0.0057 (18) |
C4 | 0.041 (2) | 0.038 (2) | 0.0414 (19) | 0.0093 (17) | 0.0003 (16) | 0.0024 (17) |
C5 | 0.066 (3) | 0.054 (2) | 0.042 (2) | 0.011 (2) | −0.007 (2) | 0.0043 (19) |
C6 | 0.067 (3) | 0.054 (3) | 0.055 (2) | 0.017 (2) | −0.013 (2) | 0.013 (2) |
C7 | 0.060 (3) | 0.041 (2) | 0.056 (2) | 0.013 (2) | −0.005 (2) | 0.007 (2) |
C8 | 0.046 (2) | 0.037 (2) | 0.0417 (19) | 0.0068 (18) | 0.0014 (17) | 0.0027 (17) |
C9 | 0.068 (3) | 0.041 (2) | 0.055 (2) | 0.001 (2) | −0.010 (2) | 0.006 (2) |
C11 | 0.043 (2) | 0.042 (2) | 0.056 (2) | −0.0035 (18) | −0.0037 (18) | 0.007 (2) |
C12 | 0.0342 (19) | 0.0336 (19) | 0.0398 (18) | 0.0037 (15) | 0.0008 (15) | 0.0043 (16) |
C13 | 0.0319 (18) | 0.0322 (18) | 0.0377 (17) | 0.0019 (15) | −0.0034 (15) | 0.0031 (15) |
C14 | 0.039 (2) | 0.045 (2) | 0.0410 (19) | 0.0022 (18) | 0.0048 (16) | 0.0032 (17) |
C15 | 0.046 (2) | 0.054 (2) | 0.0400 (19) | −0.0024 (19) | 0.0048 (18) | 0.0046 (19) |
C16 | 0.047 (2) | 0.038 (2) | 0.042 (2) | −0.0067 (18) | −0.0008 (16) | 0.0084 (18) |
C17 | 0.056 (2) | 0.037 (2) | 0.0431 (19) | 0.0015 (19) | −0.0081 (18) | 0.0045 (17) |
C18 | 0.041 (2) | 0.041 (2) | 0.051 (2) | 0.0092 (18) | −0.0061 (19) | 0.0014 (18) |
C19 | 0.043 (2) | 0.0327 (19) | 0.0399 (19) | −0.0008 (17) | −0.0051 (16) | 0.0004 (17) |
C20 | 0.083 (3) | 0.075 (3) | 0.050 (2) | 0.001 (3) | −0.020 (2) | 0.015 (2) |
C21 | 0.085 (3) | 0.052 (3) | 0.083 (3) | 0.030 (3) | −0.007 (3) | 0.001 (3) |
C22 | 0.087 (3) | 0.052 (3) | 0.076 (3) | 0.000 (3) | 0.000 (3) | 0.019 (2) |
C23 | 0.064 (3) | 0.060 (3) | 0.038 (2) | −0.012 (2) | 0.004 (2) | −0.002 (2) |
C24 | 0.143 (5) | 0.062 (3) | 0.056 (3) | −0.004 (3) | 0.020 (3) | −0.015 (2) |
C1A | 0.041 (2) | 0.043 (2) | 0.0389 (18) | 0.0118 (18) | 0.0010 (16) | −0.0014 (17) |
C2A | 0.048 (2) | 0.059 (3) | 0.050 (2) | 0.008 (2) | 0.0031 (19) | −0.013 (2) |
C4A | 0.048 (2) | 0.062 (3) | 0.0360 (19) | −0.009 (2) | 0.0023 (17) | 0.0004 (19) |
C5A | 0.074 (3) | 0.090 (4) | 0.0322 (19) | −0.027 (3) | −0.001 (2) | 0.001 (2) |
C6A | 0.073 (3) | 0.085 (3) | 0.043 (2) | −0.025 (3) | −0.013 (2) | 0.024 (2) |
C7A | 0.054 (2) | 0.057 (3) | 0.045 (2) | −0.020 (2) | −0.0078 (19) | 0.016 (2) |
C8A | 0.0341 (19) | 0.048 (2) | 0.0374 (18) | −0.0072 (17) | −0.0020 (15) | 0.0089 (17) |
C9A | 0.041 (2) | 0.053 (2) | 0.0372 (19) | −0.010 (2) | 0.0041 (17) | 0.0028 (19) |
C11A | 0.037 (2) | 0.063 (3) | 0.048 (2) | −0.0024 (19) | 0.0049 (17) | −0.009 (2) |
C12A | 0.0348 (19) | 0.049 (2) | 0.0320 (17) | −0.0035 (17) | 0.0030 (15) | −0.0006 (17) |
C13A | 0.0362 (19) | 0.0389 (19) | 0.0327 (17) | 0.0032 (16) | 0.0031 (15) | 0.0034 (15) |
C14A | 0.042 (2) | 0.040 (2) | 0.056 (2) | 0.0104 (18) | 0.0109 (19) | 0.011 (2) |
C15A | 0.060 (3) | 0.041 (2) | 0.070 (3) | 0.009 (2) | 0.027 (2) | 0.009 (2) |
C16A | 0.058 (2) | 0.037 (2) | 0.061 (2) | −0.001 (2) | 0.014 (2) | 0.004 (2) |
C17A | 0.103 (4) | 0.037 (2) | 0.046 (2) | 0.015 (2) | 0.004 (2) | 0.0053 (19) |
C18A | 0.070 (3) | 0.045 (2) | 0.049 (2) | 0.025 (2) | −0.011 (2) | 0.000 (2) |
C19A | 0.048 (2) | 0.036 (2) | 0.049 (2) | 0.0019 (18) | 0.0008 (17) | 0.0035 (18) |
C20A | 0.162 (5) | 0.063 (3) | 0.049 (3) | 0.024 (4) | 0.003 (3) | 0.007 (2) |
C21A | 0.081 (3) | 0.069 (3) | 0.084 (3) | −0.009 (3) | −0.018 (3) | 0.035 (3) |
C22A | 0.076 (3) | 0.089 (4) | 0.051 (2) | −0.040 (3) | 0.000 (2) | 0.021 (2) |
C23A | 0.066 (3) | 0.065 (3) | 0.051 (3) | −0.012 (2) | 0.001 (2) | −0.003 (2) |
C24A | 0.081 (3) | 0.067 (3) | 0.072 (3) | −0.021 (3) | 0.011 (3) | −0.021 (3) |
O1—C2 | 1.214 (4) | C20—H20B | 0.9600 |
O2—C9 | 1.197 (5) | C20—H20C | 0.9600 |
O3—C2 | 1.323 (4) | C21—H21A | 0.9600 |
O3—C4 | 1.457 (4) | C21—H21B | 0.9600 |
O4—C14 | 1.434 (4) | C21—H21C | 0.9600 |
O4—H4 | 0.8200 | C22—H22A | 0.9600 |
O5—C18 | 1.204 (4) | C22—H22B | 0.9600 |
O6—C23 | 1.356 (4) | C22—H22C | 0.9600 |
O6—C19 | 1.446 (4) | C23—C24 | 1.500 (6) |
O7—C23 | 1.179 (5) | C24—H24A | 0.9600 |
O10—C9 | 1.368 (5) | C24—H24B | 0.9600 |
O10—C11 | 1.434 (4) | C24—H24C | 0.9600 |
O1A—C2A | 1.196 (4) | C1A—C2A | 1.522 (5) |
O2A—C9A | 1.205 (4) | C1A—C18A | 1.540 (5) |
O3A—C2A | 1.347 (5) | C1A—C19A | 1.550 (5) |
O3A—C4A | 1.451 (5) | C1A—C13A | 1.581 (5) |
O4A—C14A | 1.427 (4) | C4A—C5A | 1.502 (5) |
O4A—H4A | 0.8200 | C4A—C12A | 1.519 (5) |
O5A—C18A | 1.201 (5) | C4A—H4C | 0.9800 |
O6A—C23A | 1.338 (5) | C5A—C6A | 1.516 (6) |
O6A—C19A | 1.445 (4) | C5A—H5C | 0.9700 |
O7A—C23A | 1.187 (5) | C5A—H5D | 0.9700 |
O10A—C9A | 1.346 (4) | C6A—C7A | 1.522 (6) |
O10A—C11A | 1.450 (4) | C6A—H6C | 0.9700 |
C1—C2 | 1.511 (5) | C6A—H6D | 0.9700 |
C1—C19 | 1.545 (5) | C7A—C21A | 1.538 (6) |
C1—C18 | 1.549 (5) | C7A—C22A | 1.541 (6) |
C1—C13 | 1.581 (5) | C7A—C8A | 1.576 (5) |
C4—C5 | 1.500 (5) | C8A—C9A | 1.505 (5) |
C4—C12 | 1.523 (5) | C8A—C12A | 1.547 (5) |
C4—H4B | 0.9800 | C8A—H8A | 0.9800 |
C5—C6 | 1.523 (5) | C11A—C12A | 1.536 (5) |
C5—H5A | 0.9700 | C11A—H11C | 0.9700 |
C5—H5B | 0.9700 | C11A—H11D | 0.9700 |
C6—C7 | 1.537 (5) | C12A—C13A | 1.549 (5) |
C6—H6A | 0.9700 | C13A—C14A | 1.534 (5) |
C6—H6B | 0.9700 | C13A—H13A | 0.9800 |
C7—C22 | 1.532 (6) | C14A—C15A | 1.516 (5) |
C7—C21 | 1.537 (5) | C14A—H14A | 0.9800 |
C7—C8 | 1.572 (5) | C15A—C16A | 1.543 (5) |
C8—C9 | 1.505 (5) | C15A—H15C | 0.9700 |
C8—C12 | 1.546 (5) | C15A—H15D | 0.9700 |
C8—H8 | 0.9800 | C16A—C17A | 1.519 (6) |
C11—C12 | 1.537 (5) | C16A—C19A | 1.519 (5) |
C11—H11A | 0.9700 | C16A—H16A | 0.9800 |
C11—H11B | 0.9700 | C17A—C18A | 1.511 (6) |
C12—C13 | 1.547 (4) | C17A—C20A | 1.530 (5) |
C13—C14 | 1.537 (4) | C17A—H17A | 0.9800 |
C13—H13 | 0.9800 | C19A—H19A | 0.9800 |
C14—C15 | 1.526 (5) | C20A—H20D | 0.9600 |
C14—H14 | 0.9800 | C20A—H20E | 0.9600 |
C15—C16 | 1.537 (5) | C20A—H20F | 0.9600 |
C15—H15A | 0.9700 | C21A—H21D | 0.9600 |
C15—H15B | 0.9700 | C21A—H21E | 0.9600 |
C16—C19 | 1.525 (5) | C21A—H21F | 0.9600 |
C16—C17 | 1.536 (5) | C22A—H22D | 0.9600 |
C16—H16 | 0.9800 | C22A—H22E | 0.9600 |
C17—C18 | 1.507 (5) | C22A—H22F | 0.9600 |
C17—C20 | 1.523 (5) | C23A—C24A | 1.488 (6) |
C17—H17 | 0.9800 | C24A—H24D | 0.9600 |
C19—H19 | 0.9800 | C24A—H24E | 0.9600 |
C20—H20A | 0.9600 | C24A—H24F | 0.9600 |
C2—O3—C4 | 117.3 (3) | H24A—C24—H24B | 109.5 |
C14—O4—H4 | 109.5 | C23—C24—H24C | 109.5 |
C23—O6—C19 | 117.4 (3) | H24A—C24—H24C | 109.5 |
C9—O10—C11 | 109.8 (3) | H24B—C24—H24C | 109.5 |
C2A—O3A—C4A | 117.6 (3) | C2A—C1A—C18A | 110.6 (3) |
C14A—O4A—H4A | 109.5 | C2A—C1A—C19A | 112.2 (3) |
C23A—O6A—C19A | 116.8 (3) | C18A—C1A—C19A | 100.9 (3) |
C9A—O10A—C11A | 110.5 (3) | C2A—C1A—C13A | 116.9 (3) |
C2—C1—C19 | 112.1 (3) | C18A—C1A—C13A | 104.7 (3) |
C2—C1—C18 | 112.0 (3) | C19A—C1A—C13A | 110.1 (3) |
C19—C1—C18 | 100.9 (3) | O1A—C2A—O3A | 119.2 (4) |
C2—C1—C13 | 115.9 (3) | O1A—C2A—C1A | 122.5 (4) |
C19—C1—C13 | 109.9 (3) | O3A—C2A—C1A | 118.3 (3) |
C18—C1—C13 | 104.7 (3) | O3A—C4A—C5A | 108.7 (3) |
O1—C2—O3 | 118.0 (3) | O3A—C4A—C12A | 107.8 (3) |
O1—C2—C1 | 122.5 (3) | C5A—C4A—C12A | 113.8 (3) |
O3—C2—C1 | 119.5 (3) | O3A—C4A—H4C | 108.8 |
O3—C4—C5 | 107.2 (3) | C5A—C4A—H4C | 108.8 |
O3—C4—C12 | 107.2 (3) | C12A—C4A—H4C | 108.8 |
C5—C4—C12 | 114.7 (3) | C4A—C5A—C6A | 109.2 (3) |
O3—C4—H4B | 109.2 | C4A—C5A—H5C | 109.8 |
C5—C4—H4B | 109.2 | C6A—C5A—H5C | 109.8 |
C12—C4—H4B | 109.2 | C4A—C5A—H5D | 109.8 |
C4—C5—C6 | 108.2 (3) | C6A—C5A—H5D | 109.8 |
C4—C5—H5A | 110.1 | H5C—C5A—H5D | 108.3 |
C6—C5—H5A | 110.1 | C5A—C6A—C7A | 112.8 (4) |
C4—C5—H5B | 110.1 | C5A—C6A—H6C | 109.0 |
C6—C5—H5B | 110.1 | C7A—C6A—H6C | 109.0 |
H5A—C5—H5B | 108.4 | C5A—C6A—H6D | 109.0 |
C5—C6—C7 | 113.1 (3) | C7A—C6A—H6D | 109.0 |
C5—C6—H6A | 109.0 | H6C—C6A—H6D | 107.8 |
C7—C6—H6A | 109.0 | C6A—C7A—C21A | 109.4 (4) |
C5—C6—H6B | 109.0 | C6A—C7A—C22A | 109.8 (4) |
C7—C6—H6B | 109.0 | C21A—C7A—C22A | 107.5 (4) |
H6A—C6—H6B | 107.8 | C6A—C7A—C8A | 108.6 (3) |
C22—C7—C6 | 110.2 (3) | C21A—C7A—C8A | 107.5 (3) |
C22—C7—C21 | 107.9 (3) | C22A—C7A—C8A | 113.9 (3) |
C6—C7—C21 | 108.3 (3) | C9A—C8A—C12A | 102.2 (3) |
C22—C7—C8 | 114.0 (3) | C9A—C8A—C7A | 109.2 (3) |
C6—C7—C8 | 108.6 (3) | C12A—C8A—C7A | 117.4 (3) |
C21—C7—C8 | 107.7 (3) | C9A—C8A—H8A | 109.2 |
C9—C8—C12 | 101.6 (3) | C12A—C8A—H8A | 109.2 |
C9—C8—C7 | 110.6 (3) | C7A—C8A—H8A | 109.2 |
C12—C8—C7 | 117.1 (3) | O2A—C9A—O10A | 120.4 (3) |
C9—C8—H8 | 109.0 | O2A—C9A—C8A | 129.1 (4) |
C12—C8—H8 | 109.0 | O10A—C9A—C8A | 110.4 (3) |
C7—C8—H8 | 109.0 | O10A—C11A—C12A | 105.1 (3) |
O2—C9—O10 | 120.3 (4) | O10A—C11A—H11C | 110.7 |
O2—C9—C8 | 129.7 (4) | C12A—C11A—H11C | 110.7 |
O10—C9—C8 | 110.0 (3) | O10A—C11A—H11D | 110.7 |
O10—C11—C12 | 105.7 (3) | C12A—C11A—H11D | 110.7 |
O10—C11—H11A | 110.6 | H11C—C11A—H11D | 108.8 |
C12—C11—H11A | 110.6 | C4A—C12A—C11A | 112.2 (3) |
O10—C11—H11B | 110.6 | C4A—C12A—C8A | 115.3 (3) |
C12—C11—H11B | 110.6 | C11A—C12A—C8A | 101.2 (3) |
H11A—C11—H11B | 108.7 | C4A—C12A—C13A | 107.5 (3) |
C4—C12—C11 | 112.7 (3) | C11A—C12A—C13A | 107.3 (3) |
C4—C12—C8 | 114.9 (3) | C8A—C12A—C13A | 113.1 (3) |
C11—C12—C8 | 100.6 (3) | C14A—C13A—C12A | 116.6 (3) |
C4—C12—C13 | 108.2 (3) | C14A—C13A—C1A | 111.0 (3) |
C11—C12—C13 | 107.0 (3) | C12A—C13A—C1A | 110.2 (3) |
C8—C12—C13 | 113.2 (3) | C14A—C13A—H13A | 106.1 |
C14—C13—C12 | 117.1 (3) | C12A—C13A—H13A | 106.1 |
C14—C13—C1 | 112.6 (3) | C1A—C13A—H13A | 106.1 |
C12—C13—C1 | 109.3 (2) | O4A—C14A—C15A | 110.4 (3) |
C14—C13—H13 | 105.7 | O4A—C14A—C13A | 109.6 (3) |
C12—C13—H13 | 105.7 | C15A—C14A—C13A | 111.1 (3) |
C1—C13—H13 | 105.7 | O4A—C14A—H14A | 108.6 |
O4—C14—C15 | 111.7 (3) | C15A—C14A—H14A | 108.6 |
O4—C14—C13 | 108.1 (2) | C13A—C14A—H14A | 108.6 |
C15—C14—C13 | 111.8 (3) | C14A—C15A—C16A | 114.4 (3) |
O4—C14—H14 | 108.4 | C14A—C15A—H15C | 108.7 |
C15—C14—H14 | 108.4 | C16A—C15A—H15C | 108.7 |
C13—C14—H14 | 108.4 | C14A—C15A—H15D | 108.7 |
C14—C15—C16 | 115.0 (3) | C16A—C15A—H15D | 108.7 |
C14—C15—H15A | 108.5 | H15C—C15A—H15D | 107.6 |
C16—C15—H15A | 108.5 | C17A—C16A—C19A | 101.9 (3) |
C14—C15—H15B | 108.5 | C17A—C16A—C15A | 114.8 (4) |
C16—C15—H15B | 108.5 | C19A—C16A—C15A | 107.9 (3) |
H15A—C15—H15B | 107.5 | C17A—C16A—H16A | 110.6 |
C19—C16—C17 | 101.8 (3) | C19A—C16A—H16A | 110.6 |
C19—C16—C15 | 109.0 (3) | C15A—C16A—H16A | 110.6 |
C17—C16—C15 | 114.4 (3) | C18A—C17A—C16A | 104.3 (3) |
C19—C16—H16 | 110.5 | C18A—C17A—C20A | 112.8 (4) |
C17—C16—H16 | 110.5 | C16A—C17A—C20A | 119.1 (4) |
C15—C16—H16 | 110.5 | C18A—C17A—H17A | 106.6 |
C18—C17—C20 | 114.7 (3) | C16A—C17A—H17A | 106.6 |
C18—C17—C16 | 103.2 (3) | C20A—C17A—H17A | 106.6 |
C20—C17—C16 | 119.6 (3) | O5A—C18A—C17A | 127.4 (4) |
C18—C17—H17 | 106.1 | O5A—C18A—C1A | 124.6 (4) |
C20—C17—H17 | 106.1 | C17A—C18A—C1A | 107.8 (3) |
C16—C17—H17 | 106.1 | O6A—C19A—C16A | 107.2 (3) |
O5—C18—C17 | 127.2 (3) | O6A—C19A—C1A | 110.3 (3) |
O5—C18—C1 | 124.0 (3) | C16A—C19A—C1A | 100.9 (3) |
C17—C18—C1 | 108.6 (3) | O6A—C19A—H19A | 112.6 |
O6—C19—C16 | 107.1 (3) | C16A—C19A—H19A | 112.6 |
O6—C19—C1 | 110.1 (3) | C1A—C19A—H19A | 112.6 |
C16—C19—C1 | 101.1 (3) | C17A—C20A—H20D | 109.5 |
O6—C19—H19 | 112.6 | C17A—C20A—H20E | 109.5 |
C16—C19—H19 | 112.6 | H20D—C20A—H20E | 109.5 |
C1—C19—H19 | 112.6 | C17A—C20A—H20F | 109.5 |
C17—C20—H20A | 109.5 | H20D—C20A—H20F | 109.5 |
C17—C20—H20B | 109.5 | H20E—C20A—H20F | 109.5 |
H20A—C20—H20B | 109.5 | C7A—C21A—H21D | 109.5 |
C17—C20—H20C | 109.5 | C7A—C21A—H21E | 109.5 |
H20A—C20—H20C | 109.5 | H21D—C21A—H21E | 109.5 |
H20B—C20—H20C | 109.5 | C7A—C21A—H21F | 109.5 |
C7—C21—H21A | 109.5 | H21D—C21A—H21F | 109.5 |
C7—C21—H21B | 109.5 | H21E—C21A—H21F | 109.5 |
H21A—C21—H21B | 109.5 | C7A—C22A—H22D | 109.5 |
C7—C21—H21C | 109.5 | C7A—C22A—H22E | 109.5 |
H21A—C21—H21C | 109.5 | H22D—C22A—H22E | 109.5 |
H21B—C21—H21C | 109.5 | C7A—C22A—H22F | 109.5 |
C7—C22—H22A | 109.5 | H22D—C22A—H22F | 109.5 |
C7—C22—H22B | 109.5 | H22E—C22A—H22F | 109.5 |
H22A—C22—H22B | 109.5 | O7A—C23A—O6A | 123.0 (4) |
C7—C22—H22C | 109.5 | O7A—C23A—C24A | 126.2 (4) |
H22A—C22—H22C | 109.5 | O6A—C23A—C24A | 110.7 (4) |
H22B—C22—H22C | 109.5 | C23A—C24A—H24D | 109.5 |
O7—C23—O6 | 123.4 (4) | C23A—C24A—H24E | 109.5 |
O7—C23—C24 | 126.7 (4) | H24D—C24A—H24E | 109.5 |
O6—C23—C24 | 109.9 (4) | C23A—C24A—H24F | 109.5 |
C23—C24—H24A | 109.5 | H24D—C24A—H24F | 109.5 |
C23—C24—H24B | 109.5 | H24E—C24A—H24F | 109.5 |
C4—O3—C2—O1 | 178.7 (3) | C4A—O3A—C2A—O1A | −176.8 (4) |
C4—O3—C2—C1 | −2.3 (5) | C4A—O3A—C2A—C1A | 2.1 (5) |
C19—C1—C2—O1 | 85.4 (4) | C18A—C1A—C2A—O1A | −32.5 (5) |
C18—C1—C2—O1 | −27.2 (5) | C19A—C1A—C2A—O1A | 79.3 (5) |
C13—C1—C2—O1 | −147.3 (3) | C13A—C1A—C2A—O1A | −152.1 (4) |
C19—C1—C2—O3 | −93.5 (4) | C18A—C1A—C2A—O3A | 148.6 (3) |
C18—C1—C2—O3 | 153.9 (3) | C19A—C1A—C2A—O3A | −99.6 (4) |
C13—C1—C2—O3 | 33.8 (5) | C13A—C1A—C2A—O3A | 29.0 (5) |
C2—O3—C4—C5 | −174.0 (3) | C2A—O3A—C4A—C5A | −176.9 (3) |
C2—O3—C4—C12 | −50.4 (4) | C2A—O3A—C4A—C12A | −53.1 (4) |
O3—C4—C5—C6 | 174.9 (3) | O3A—C4A—C5A—C6A | 176.0 (3) |
C12—C4—C5—C6 | 56.0 (4) | C12A—C4A—C5A—C6A | 55.8 (4) |
C4—C5—C6—C7 | −65.2 (4) | C4A—C5A—C6A—C7A | −66.1 (4) |
C5—C6—C7—C22 | −69.4 (4) | C5A—C6A—C7A—C21A | 173.1 (3) |
C5—C6—C7—C21 | 172.8 (3) | C5A—C6A—C7A—C22A | −69.2 (4) |
C5—C6—C7—C8 | 56.2 (4) | C5A—C6A—C7A—C8A | 55.9 (4) |
C22—C7—C8—C9 | −32.3 (4) | C6A—C7A—C8A—C9A | −154.6 (3) |
C6—C7—C8—C9 | −155.6 (3) | C21A—C7A—C8A—C9A | 87.1 (4) |
C21—C7—C8—C9 | 87.4 (4) | C22A—C7A—C8A—C9A | −31.9 (5) |
C22—C7—C8—C12 | 83.5 (4) | C6A—C7A—C8A—C12A | −39.0 (4) |
C6—C7—C8—C12 | −39.9 (4) | C21A—C7A—C8A—C12A | −157.3 (3) |
C21—C7—C8—C12 | −156.9 (3) | C22A—C7A—C8A—C12A | 83.8 (4) |
C11—O10—C9—O2 | −178.4 (3) | C11A—O10A—C9A—O2A | 179.7 (3) |
C11—O10—C9—C8 | 3.8 (4) | C11A—O10A—C9A—C8A | 1.7 (4) |
C12—C8—C9—O2 | 158.2 (4) | C12A—C8A—C9A—O2A | 161.0 (4) |
C7—C8—C9—O2 | −76.8 (5) | C7A—C8A—C9A—O2A | −74.0 (5) |
C12—C8—C9—O10 | −24.3 (4) | C12A—C8A—C9A—O10A | −21.2 (3) |
C7—C8—C9—O10 | 100.8 (3) | C7A—C8A—C9A—O10A | 103.8 (3) |
C9—O10—C11—C12 | 18.8 (4) | C9A—O10A—C11A—C12A | 18.9 (4) |
O3—C4—C12—C11 | −46.2 (4) | O3A—C4A—C12A—C11A | −45.7 (4) |
C5—C4—C12—C11 | 72.7 (4) | C5A—C4A—C12A—C11A | 75.0 (4) |
O3—C4—C12—C8 | −160.5 (3) | O3A—C4A—C12A—C8A | −160.8 (3) |
C5—C4—C12—C8 | −41.7 (4) | C5A—C4A—C12A—C8A | −40.1 (4) |
O3—C4—C12—C13 | 71.9 (3) | O3A—C4A—C12A—C13A | 72.1 (3) |
C5—C4—C12—C13 | −169.2 (3) | C5A—C4A—C12A—C13A | −167.3 (3) |
O10—C11—C12—C4 | −155.1 (3) | O10A—C11A—C12A—C4A | −153.8 (3) |
O10—C11—C12—C8 | −32.3 (3) | O10A—C11A—C12A—C8A | −30.4 (3) |
O10—C11—C12—C13 | 86.1 (3) | O10A—C11A—C12A—C13A | 88.4 (3) |
C9—C8—C12—C4 | 154.3 (3) | C9A—C8A—C12A—C4A | 151.6 (3) |
C7—C8—C12—C4 | 33.6 (4) | C7A—C8A—C12A—C4A | 32.2 (4) |
C9—C8—C12—C11 | 33.0 (3) | C9A—C8A—C12A—C11A | 30.4 (3) |
C7—C8—C12—C11 | −87.6 (4) | C7A—C8A—C12A—C11A | −89.1 (3) |
C9—C8—C12—C13 | −80.8 (3) | C9A—C8A—C12A—C13A | −84.1 (3) |
C7—C8—C12—C13 | 158.6 (3) | C7A—C8A—C12A—C13A | 156.4 (3) |
C4—C12—C13—C14 | 89.6 (3) | C4A—C12A—C13A—C14A | 87.7 (4) |
C11—C12—C13—C14 | −148.8 (3) | C11A—C12A—C13A—C14A | −151.5 (3) |
C8—C12—C13—C14 | −38.9 (4) | C8A—C12A—C13A—C14A | −40.8 (4) |
C4—C12—C13—C1 | −39.9 (3) | C4A—C12A—C13A—C1A | −40.1 (4) |
C11—C12—C13—C1 | 81.8 (3) | C11A—C12A—C13A—C1A | 80.8 (3) |
C8—C12—C13—C1 | −168.4 (3) | C8A—C12A—C13A—C1A | −168.5 (3) |
C2—C1—C13—C14 | −140.9 (3) | C2A—C1A—C13A—C14A | −137.7 (3) |
C19—C1—C13—C14 | −12.5 (4) | C18A—C1A—C13A—C14A | 99.6 (3) |
C18—C1—C13—C14 | 95.1 (3) | C19A—C1A—C13A—C14A | −8.1 (4) |
C2—C1—C13—C12 | −9.1 (4) | C2A—C1A—C13A—C12A | −6.9 (4) |
C19—C1—C13—C12 | 119.3 (3) | C18A—C1A—C13A—C12A | −129.6 (3) |
C18—C1—C13—C12 | −133.0 (3) | C19A—C1A—C13A—C12A | 122.7 (3) |
C12—C13—C14—O4 | −46.4 (4) | C12A—C13A—C14A—O4A | −52.4 (4) |
C1—C13—C14—O4 | 81.4 (3) | C1A—C13A—C14A—O4A | 74.9 (4) |
C12—C13—C14—C15 | −169.7 (3) | C12A—C13A—C14A—C15A | −174.7 (3) |
C1—C13—C14—C15 | −41.8 (4) | C1A—C13A—C14A—C15A | −47.4 (4) |
O4—C14—C15—C16 | −81.2 (4) | O4A—C14A—C15A—C16A | −78.4 (4) |
C13—C14—C15—C16 | 40.0 (4) | C13A—C14A—C15A—C16A | 43.4 (5) |
C14—C15—C16—C19 | 17.9 (4) | C14A—C15A—C16A—C17A | −94.9 (4) |
C14—C15—C16—C17 | −95.2 (4) | C14A—C15A—C16A—C19A | 18.0 (5) |
C19—C16—C17—C18 | −37.2 (3) | C19A—C16A—C17A—C18A | −35.4 (4) |
C15—C16—C17—C18 | 80.1 (3) | C15A—C16A—C17A—C18A | 81.0 (4) |
C19—C16—C17—C20 | −166.1 (3) | C19A—C16A—C17A—C20A | −162.3 (4) |
C15—C16—C17—C20 | −48.7 (5) | C15A—C16A—C17A—C20A | −45.9 (5) |
C20—C17—C18—O5 | −32.7 (6) | C16A—C17A—C18A—O5A | −167.4 (4) |
C16—C17—C18—O5 | −164.5 (4) | C20A—C17A—C18A—O5A | −36.6 (6) |
C20—C17—C18—C1 | 142.8 (3) | C16A—C17A—C18A—C1A | 8.3 (4) |
C16—C17—C18—C1 | 11.0 (4) | C20A—C17A—C18A—C1A | 139.0 (4) |
C2—C1—C18—O5 | −46.0 (5) | C2A—C1A—C18A—O5A | −44.0 (5) |
C19—C1—C18—O5 | −165.4 (4) | C19A—C1A—C18A—O5A | −162.9 (4) |
C13—C1—C18—O5 | 80.5 (4) | C13A—C1A—C18A—O5A | 82.7 (5) |
C2—C1—C18—C17 | 138.3 (3) | C2A—C1A—C18A—C17A | 140.2 (3) |
C19—C1—C18—C17 | 18.9 (3) | C19A—C1A—C18A—C17A | 21.3 (4) |
C13—C1—C18—C17 | −95.2 (3) | C13A—C1A—C18A—C17A | −93.1 (3) |
C23—O6—C19—C16 | −152.6 (3) | C23A—O6A—C19A—C16A | −154.4 (3) |
C23—O6—C19—C1 | 98.3 (4) | C23A—O6A—C19A—C1A | 96.6 (4) |
C17—C16—C19—O6 | −65.6 (3) | C17A—C16A—C19A—O6A | −66.5 (4) |
C15—C16—C19—O6 | 173.2 (3) | C15A—C16A—C19A—O6A | 172.2 (3) |
C17—C16—C19—C1 | 49.6 (3) | C17A—C16A—C19A—C1A | 48.9 (4) |
C15—C16—C19—C1 | −71.5 (3) | C15A—C16A—C19A—C1A | −72.4 (4) |
C2—C1—C19—O6 | −47.8 (4) | C2A—C1A—C19A—O6A | −47.3 (4) |
C18—C1—C19—O6 | 71.5 (3) | C18A—C1A—C19A—O6A | 70.4 (3) |
C13—C1—C19—O6 | −178.3 (2) | C13A—C1A—C19A—O6A | −179.4 (3) |
C2—C1—C19—C16 | −160.9 (3) | C2A—C1A—C19A—C16A | −160.4 (3) |
C18—C1—C19—C16 | −41.5 (3) | C18A—C1A—C19A—C16A | −42.7 (3) |
C13—C1—C19—C16 | 68.7 (3) | C13A—C1A—C19A—C16A | 67.6 (3) |
C19—O6—C23—O7 | −1.9 (6) | C19A—O6A—C23A—O7A | −0.2 (6) |
C19—O6—C23—C24 | 178.6 (3) | C19A—O6A—C23A—C24A | −177.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O2A | 0.82 | 2.27 | 2.980 (4) | 145 |
O4A—H4A···O1i | 0.82 | 1.91 | 2.678 (4) | 156 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C22H28O8 |
Mr | 420.44 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 11.9500 (11), 13.7531 (16), 25.377 (3) |
V (Å3) | 4170.7 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.50 × 0.46 × 0.27 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.951, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20027, 4122, 2948 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.095, 1.07 |
No. of reflections | 4122 |
No. of parameters | 550 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.17 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O2A | 0.82 | 2.27 | 2.980 (4) | 144.9 |
O4A—H4A···O1i | 0.82 | 1.91 | 2.678 (4) | 156.0 |
Symmetry code: (i) x+1, y, z. |
Molecules | I | II | |||||
Puckering parameters | Q | θ | φ | Q | θ | φ | Conformation |
Ring A | 0.527 (4) | 159.0 (5) | 271.9 (12) | 0.524 (4) | 157.5 (5) | 272.1 (12) | chair |
Ring B | 0.661 (4) | 107.6 (3) | 94.6 (3) | 0.646 (4) | 109.8 (3) | 95.3 (3) | screw-boat |
Ring C | 0.823 (4) | 79.0 (3) | 297.7 (3) | 0.849 (4) | 80.8 (3) | 295.5 (3) | boat |
Puckering parameters | Q2 | φ2 | Q2 | φ2 | Conformation | ||
Ring D | 0.485 (4) | 131.2 (5) | 0.481 (4) | 134.5 (5) | twist | ||
Ring E | 0.349 (4) | 282.0 (6) | 0.324 (4) | 284.9 (6) | envelope |
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Since the natural diterpenoid Macrocalyxin J exhibits cytotoxicity in vitro against cultures of Hela cells (Shi et al., 2007), we have derived the title compound from it.
Two unique molecules are present in the asymmetric unit, both molecule I (Fig.1) and molecule II (Fig.2) are built up from five fused rings, three six membered (A,B,C,A',B'and C') and two five membered rings (D,E,D' and E'). This two molecules are linked by a O—H···O hydrogen bond to form a pseudo dimer. The dimer are further interconnected through O—H···O hydrogen bonds to build up a chain parallel to the a axis (Table 1, Fig.3).
The conformations of the different rings extracted from the puckering parameters (Cremer & Pople, 1975) are given in Table 2. Ring A and A' adopt a chair conformation, ring B and B' exist in a screw-boat conformation and rings C and C' adopt a boat conformation. Rings D and D' present a twist conformation whereas rings E and E' adopt an envelope conformation.
Since the title compound was prepared from Macrocalyxin J, which was isolated from the same plant (i.e. Rabdosia macrocalyx) as Macrocalyxin A, the configuration can be deduced from the known chirality of the Macrocalyxin A (Shi et al., 2003),and thus Fig. 1 and Fig. 2 represents the correct absolute configuration.