Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052099/fj2053sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052099/fj2053Isup2.hkl |
CCDC reference: 667443
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.051
- wR factor = 0.115
- Data-to-parameter ratio = 8.5
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.744 1.000 Tmin(prime) and Tmax expected: 0.949 0.968 RR(prime) = 0.758 Please check that your absorption correction is appropriate. RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.130 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.76 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.97 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.22 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C47 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.968 Tmax scaled 0.968 Tmin scaled 0.720 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 27.00 From the CIF: _reflns_number_total 4945 Count of symmetry unique reflns 4959 Completeness (_total/calc) 99.72% 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 C4 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C28 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C36 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C37 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C38 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C40 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C43 = . R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 5
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 18 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 9 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); Wang et al. (1984).
Cooling in ice-water bath, 0.2 ml Jones reagent was added to a solution of Macrocalyxin J (200 mg; isolated from Rabdosia macrocalyx) in acetone (8 ml), after stirring for 20 minutes, filtrated and the solution was added 120 ml 15% NaHCO3 in water, the mixture extracted 3 times with 90 ml diethyl ether, after evaporation of the solvent, a white residue was gained. Recrystallization with methanol gave the title compound as colorless crystals.
Crystals suitable for X-ray structure analysis were obtained by slow evaporation from a solution of methanol at room temperature.
H atoms bonded to O atoms and some H atoms bonded to CH were located in a difference map, and with Uĩso~(H) = 1.2U~eq~(O, C). Other 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). Both independent molecules have the same absolute configuration, although this could not be determined reliably from the X-ray data and Friedel reflections were merged.
Since the natural diterpenoid Macrocalyxin J exhibits cytotoxicity in vitro against cultures of Hela cells and the IC50 =31.597µg/ml (Shi et al., 2007), we have derived the title compound from it.
The crystal packing is shown in Fig. 3. Two unique molecules are present in the asymmetric unit, both molecule 1 (Fig.1) and molecule 2 (Fig.2) are built up from five fused rings, three six membered and two five membered rings. Some geometrical features of these rings were investigated using PLATON (Spek, 2003).
For the molecule 1, cyclohexane ring A (C4—C8/C12) adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.5295 (42) Å, and θ= 157.69 (43) and φ = 271.5 (11) °, ring B (O3/C2/C1/C13/C12/C4) exists in a screw-boat conformation (Q = 0.6672 (33) Å, θ = 108.66 (28) and φ = 92.0 (3) °), ring C (C1/C13—C16/C19) adopt the boat conformation (Q = 0.8109 (35) Å, θ = 79.21 (24) and φ = 294.2 (2) °). The two five-membered rings, ring D (C1/C18/C17/C16/C19) adopts an envelope conformation with puckering parameters Q2 = 0.4565 (34) Å, and φ2 = 143.6 (4)° (envelope on C19), the ring E (O10/C9/C8/C12/C11) adopts an envelope conformation with puckering parameters Q2 = 0.3341 (36) Å, and φ2 = 284.7 (6)° (envelope on C12).
For the molecule 2, cyclohexane ring A' (C28—C32/C36) adopts a chair conformation with puckering parameters Q = 0.5312 (40) Å, and θ= 156.14 (41) and φ =274.4 (10) °, ring B' (O27/C26/C25/C37/C36/C28) exists in a screw-boat conformation (Q = 0.6421 (36) Å, and θ= 110.70 (31) and φ =94.7 (3) °), ring C' (C25/C37—C40/C43) adopt the boat conformation (Q = 0.8400 (37) Å, θ = 80.52 (25) and φ = 293.6 (3)°). The two five-membered rings, ring D' (C25/C42/C41/C40/C43) adopts an envelope conformation with puckering parameters Q2 = 0.4526 (38) Å, and φ2 = 146.0 (5)° (envelope on C43), the ring E' (O34/C33/C32/C36/C35) adopts an envelope conformation with puckering parameters Q2 = 0.3156 (35) Å, and φ2 = 284.8 (6) ° (envelope on C36).
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); Wang et al. (1984).
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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
C22H26O8 | F(000) = 1776 |
Mr = 418.43 | Dx = 1.362 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5228 reflections |
a = 12.0055 (11) Å | θ = 4.7–43.5° |
b = 13.5835 (13) Å | µ = 0.10 mm−1 |
c = 25.027 (2) Å | T = 293 K |
V = 4081.3 (6) Å3 | Prismatic, colorless |
Z = 8 | 0.49 × 0.43 × 0.32 mm |
Bruker SMART CCD area-detector diffractometer | 4945 independent reflections |
Radiation source: fine-focus sealed tube | 3810 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.130 |
φ and ω scans | θmax = 27.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −13→15 |
Tmin = 0.744, Tmax = 1.000 | k = −16→17 |
24111 measured reflections | l = −31→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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0476P)2] where P = (Fo2 + 2Fc2)/3 |
4945 reflections | (Δ/σ)max < 0.001 |
583 parameters | Δρmax = 0.17 e Å−3 |
5 restraints | Δρmin = −0.18 e Å−3 |
C22H26O8 | V = 4081.3 (6) Å3 |
Mr = 418.43 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 12.0055 (11) Å | µ = 0.10 mm−1 |
b = 13.5835 (13) Å | T = 293 K |
c = 25.027 (2) Å | 0.49 × 0.43 × 0.32 mm |
Bruker SMART CCD area-detector diffractometer | 4945 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 3810 reflections with I > 2σ(I) |
Tmin = 0.744, Tmax = 1.000 | Rint = 0.130 |
24111 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 5 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.17 e Å−3 |
4945 reflections | Δρmin = −0.18 e Å−3 |
583 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 | −0.0773 (2) | 0.39858 (19) | 0.15867 (9) | 0.0571 (7) | |
O2 | 0.0191 (3) | −0.0582 (2) | 0.03545 (10) | 0.0745 (9) | |
O3 | 0.0225 (2) | 0.27304 (16) | 0.18225 (8) | 0.0443 (5) | |
O4 | 0.2759 (2) | 0.22386 (19) | 0.08037 (10) | 0.0505 (6) | |
O5 | −0.1365 (2) | 0.36138 (18) | 0.04604 (10) | 0.0557 (6) | |
O6 | 0.1069 (2) | 0.50275 (16) | 0.10433 (8) | 0.0479 (6) | |
O7 | 0.1822 (3) | 0.4751 (2) | 0.18441 (10) | 0.0726 (8) | |
O10 | −0.0833 (2) | 0.05219 (18) | 0.07849 (10) | 0.0533 (6) | |
O25 | 0.4868 (2) | 0.8092 (2) | 0.15326 (11) | 0.0702 (8) | |
O26 | 0.4933 (2) | 0.31505 (19) | 0.05534 (9) | 0.0564 (7) | |
O27 | 0.5162 (2) | 0.66457 (19) | 0.18918 (9) | 0.0559 (7) | |
O28 | 0.7958 (2) | 0.5540 (2) | 0.12833 (11) | 0.0574 (7) | |
O29 | 0.4717 (2) | 0.7662 (2) | 0.03890 (11) | 0.0700 (8) | |
O30 | 0.7150 (2) | 0.85219 (17) | 0.12142 (9) | 0.0535 (6) | |
O31 | 0.7390 (3) | 0.8188 (3) | 0.20754 (12) | 0.0931 (11) | |
O34 | 0.41033 (18) | 0.45354 (18) | 0.07968 (8) | 0.0470 (6) | |
C1 | 0.0423 (3) | 0.3345 (2) | 0.09064 (11) | 0.0359 (7) | |
C2 | −0.0100 (3) | 0.3384 (2) | 0.14598 (12) | 0.0395 (7) | |
C4 | 0.1025 (3) | 0.1989 (2) | 0.16628 (12) | 0.0412 (8) | |
H4 | 0.1748 | 0.2301 | 0.1596 | 0.049* | |
C5 | 0.1133 (4) | 0.1263 (3) | 0.21173 (13) | 0.0585 (10) | |
H5A | 0.0404 | 0.1013 | 0.2216 | 0.070* | |
H5B | 0.1458 | 0.1583 | 0.2427 | 0.070* | |
C6 | 0.1873 (4) | 0.0425 (3) | 0.19322 (16) | 0.0671 (11) | |
H6A | 0.2034 | 0.0002 | 0.2235 | 0.081* | |
H6B | 0.2573 | 0.0695 | 0.1806 | 0.081* | |
C7 | 0.1356 (3) | −0.0193 (3) | 0.14880 (15) | 0.0572 (10) | |
C8 | 0.1063 (3) | 0.0509 (2) | 0.10027 (13) | 0.0432 (8) | |
C9 | 0.0142 (3) | 0.0071 (3) | 0.06754 (13) | 0.0507 (9) | |
C11 | −0.0653 (3) | 0.1293 (2) | 0.11657 (12) | 0.0428 (8) | |
H11A | −0.0862 | 0.1076 | 0.1521 | 0.051* | |
H11B | −0.1092 | 0.1868 | 0.1074 | 0.051* | |
C12 | 0.0589 (2) | 0.1534 (2) | 0.11442 (11) | 0.0345 (7) | |
C13 | 0.0763 (3) | 0.2297 (2) | 0.06897 (11) | 0.0336 (6) | |
H13 | 0.0215 | 0.2132 | 0.0414 | 0.040* | |
C14 | 0.1898 (3) | 0.2287 (2) | 0.04108 (12) | 0.0413 (7) | |
H14 | 0.1941 | 0.1690 | 0.0192 | 0.050* | |
C15 | 0.2046 (3) | 0.3179 (2) | 0.00380 (12) | 0.0448 (8) | |
H15A | 0.1711 | 0.3027 | −0.0305 | 0.054* | |
H15B | 0.2836 | 0.3285 | −0.0020 | 0.054* | |
C16 | 0.1526 (3) | 0.4140 (2) | 0.02532 (12) | 0.0426 (8) | |
H16 | 0.1971 | 0.4716 | 0.0152 | 0.051* | |
C17 | 0.0344 (3) | 0.4247 (2) | 0.00754 (12) | 0.0481 (9) | |
C18 | −0.0376 (3) | 0.3743 (2) | 0.04759 (12) | 0.0415 (8) | |
C19 | 0.1400 (3) | 0.4067 (2) | 0.08557 (12) | 0.0411 (8) | |
C20 | −0.0059 (4) | 0.4687 (3) | −0.03553 (14) | 0.0744 (13) | |
H20A | −0.0823 | 0.4690 | −0.0418 | 0.089* | |
H20B | 0.0421 | 0.4992 | −0.0595 | 0.089* | |
C21 | 0.2210 (4) | −0.0943 (3) | 0.12855 (19) | 0.0821 (14) | |
H21A | 0.2889 | −0.0610 | 0.1195 | 0.123* | |
H21B | 0.1921 | −0.1270 | 0.0975 | 0.123* | |
H21C | 0.2355 | −0.1420 | 0.1560 | 0.123* | |
C22 | 0.0342 (4) | −0.0769 (3) | 0.16967 (17) | 0.0720 (12) | |
H22A | 0.0558 | −0.1156 | 0.2000 | 0.108* | |
H22B | 0.0067 | −0.1195 | 0.1420 | 0.108* | |
H22C | −0.0232 | −0.0315 | 0.1800 | 0.108* | |
C23 | 0.1326 (3) | 0.5276 (3) | 0.15509 (14) | 0.0525 (9) | |
C24 | 0.0901 (5) | 0.6276 (3) | 0.16802 (16) | 0.0821 (15) | |
H24A | 0.1184 | 0.6478 | 0.2022 | 0.123* | |
H24B | 0.0102 | 0.6264 | 0.1691 | 0.123* | |
H24C | 0.1143 | 0.6732 | 0.1411 | 0.123* | |
C25 | 0.6069 (3) | 0.7044 (2) | 0.10372 (12) | 0.0377 (7) | |
C26 | 0.5321 (3) | 0.7303 (3) | 0.14997 (14) | 0.0497 (9) | |
C28 | 0.5763 (3) | 0.5727 (3) | 0.18558 (12) | 0.0458 (8) | |
C29 | 0.5426 (3) | 0.5069 (3) | 0.23096 (12) | 0.0622 (11) | |
H29A | 0.4624 | 0.4978 | 0.2309 | 0.075* | |
H29B | 0.5637 | 0.5365 | 0.2647 | 0.075* | |
C30 | 0.6000 (4) | 0.4088 (3) | 0.22445 (13) | 0.0653 (11) | |
H30A | 0.5882 | 0.3698 | 0.2564 | 0.078* | |
H30B | 0.6795 | 0.4196 | 0.2207 | 0.078* | |
C31 | 0.5579 (3) | 0.3511 (3) | 0.17602 (13) | 0.0532 (9) | |
C32 | 0.5758 (3) | 0.4175 (2) | 0.12488 (12) | 0.0396 (7) | |
C33 | 0.4935 (3) | 0.3876 (2) | 0.08301 (12) | 0.0420 (8) | |
C35 | 0.4291 (3) | 0.5328 (3) | 0.11635 (12) | 0.0438 (8) | |
H35A | 0.3837 | 0.5247 | 0.1481 | 0.053* | |
H35B | 0.4109 | 0.5954 | 0.0999 | 0.053* | |
C36 | 0.5532 (2) | 0.5285 (2) | 0.13060 (11) | 0.0361 (7) | |
C37 | 0.6168 (3) | 0.5915 (2) | 0.08923 (11) | 0.0345 (7) | |
H37 | 0.5773 | 0.5829 | 0.0553 | 0.041* | |
C38 | 0.7378 (3) | 0.5607 (3) | 0.07876 (13) | 0.0439 (8) | |
C39 | 0.7965 (3) | 0.6321 (2) | 0.04099 (14) | 0.0517 (9) | |
H39A | 0.7759 | 0.6163 | 0.0045 | 0.062* | |
H39B | 0.8763 | 0.6232 | 0.0443 | 0.062* | |
C40 | 0.7676 (3) | 0.7411 (3) | 0.05215 (14) | 0.0485 (9) | |
C41 | 0.6689 (3) | 0.7737 (3) | 0.02033 (13) | 0.0539 (9) | |
C42 | 0.5664 (3) | 0.7532 (3) | 0.05151 (13) | 0.0488 (9) | |
C43 | 0.7246 (3) | 0.7493 (2) | 0.10914 (13) | 0.0413 (8) | |
C44 | 0.6660 (5) | 0.8120 (3) | −0.02801 (16) | 0.0833 (15) | |
H44A | 0.5980 | 0.8272 | −0.0438 | 0.100* | |
H44B | 0.7320 | 0.8239 | −0.0464 | 0.100* | |
C45 | 0.6298 (4) | 0.2586 (3) | 0.16936 (19) | 0.0791 (13) | |
H45A | 0.7057 | 0.2775 | 0.1630 | 0.119* | |
H45B | 0.6030 | 0.2209 | 0.1396 | 0.119* | |
H45C | 0.6258 | 0.2196 | 0.2013 | 0.119* | |
C46 | 0.4377 (4) | 0.3195 (3) | 0.18463 (14) | 0.0650 (12) | |
H46A | 0.4316 | 0.2851 | 0.2180 | 0.097* | |
H46B | 0.4151 | 0.2769 | 0.1560 | 0.097* | |
H46C | 0.3906 | 0.3766 | 0.1853 | 0.097* | |
C47 | 0.7231 (4) | 0.8770 (3) | 0.17307 (16) | 0.0588 (10) | |
C48 | 0.7040 (4) | 0.9838 (3) | 0.18026 (18) | 0.0796 (13) | |
H48A | 0.6256 | 0.9972 | 0.1787 | 0.119* | |
H48B | 0.7413 | 1.0194 | 0.1524 | 0.119* | |
H48C | 0.7328 | 1.0040 | 0.2143 | 0.119* | |
H8 | 0.171 (3) | 0.063 (2) | 0.0796 (13) | 0.049 (10)* | |
H19 | 0.2078 (18) | 0.385 (2) | 0.1015 (10) | 0.031 (8)* | |
H28 | 0.6554 (17) | 0.589 (2) | 0.1872 (12) | 0.045 (9)* | |
H32 | 0.653 (3) | 0.402 (2) | 0.1139 (13) | 0.048 (9)* | |
H38 | 0.740 (3) | 0.495 (3) | 0.0650 (11) | 0.037 (8)* | |
H40 | 0.830 (3) | 0.783 (3) | 0.0480 (13) | 0.048 (10)* | |
H43 | 0.768 (3) | 0.714 (3) | 0.1363 (14) | 0.055 (10)* | |
H4A | 0.336 (3) | 0.234 (4) | 0.0637 (16) | 0.096 (18)* | |
H28A | 0.840 (3) | 0.509 (3) | 0.1307 (17) | 0.084 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0640 (16) | 0.0566 (15) | 0.0508 (13) | 0.0240 (14) | 0.0136 (13) | 0.0077 (12) |
O2 | 0.110 (2) | 0.0536 (16) | 0.0604 (16) | 0.0009 (16) | 0.0056 (17) | −0.0162 (14) |
O3 | 0.0565 (14) | 0.0448 (13) | 0.0315 (11) | 0.0066 (11) | 0.0022 (10) | 0.0021 (10) |
O4 | 0.0360 (13) | 0.0637 (15) | 0.0517 (13) | 0.0011 (12) | 0.0020 (12) | 0.0048 (13) |
O5 | 0.0457 (15) | 0.0590 (16) | 0.0624 (15) | 0.0119 (12) | −0.0150 (13) | −0.0013 (12) |
O6 | 0.0733 (17) | 0.0365 (12) | 0.0339 (11) | 0.0004 (11) | −0.0012 (11) | −0.0007 (10) |
O7 | 0.083 (2) | 0.093 (2) | 0.0417 (14) | 0.0110 (18) | −0.0144 (14) | −0.0084 (15) |
O10 | 0.0526 (15) | 0.0511 (14) | 0.0562 (14) | −0.0107 (12) | −0.0047 (12) | −0.0043 (12) |
O25 | 0.0668 (18) | 0.0666 (18) | 0.0772 (18) | 0.0206 (15) | 0.0115 (15) | −0.0222 (15) |
O26 | 0.0671 (17) | 0.0567 (15) | 0.0454 (13) | −0.0126 (13) | 0.0045 (12) | −0.0114 (12) |
O27 | 0.0620 (16) | 0.0645 (16) | 0.0412 (13) | −0.0083 (14) | 0.0183 (12) | −0.0139 (12) |
O28 | 0.0497 (15) | 0.0595 (17) | 0.0629 (15) | 0.0171 (13) | −0.0058 (13) | 0.0107 (13) |
O29 | 0.0652 (18) | 0.0711 (18) | 0.0738 (18) | 0.0248 (15) | −0.0267 (15) | 0.0011 (15) |
O30 | 0.0673 (17) | 0.0458 (14) | 0.0473 (14) | −0.0076 (12) | 0.0056 (13) | −0.0067 (11) |
O31 | 0.135 (3) | 0.092 (2) | 0.0515 (16) | −0.015 (2) | −0.0051 (19) | −0.0069 (17) |
O34 | 0.0410 (13) | 0.0589 (14) | 0.0412 (12) | −0.0056 (12) | −0.0066 (11) | −0.0046 (11) |
C1 | 0.0360 (17) | 0.0395 (17) | 0.0321 (15) | 0.0055 (13) | −0.0008 (13) | 0.0000 (13) |
C2 | 0.0398 (18) | 0.0377 (17) | 0.0409 (17) | 0.0007 (15) | 0.0008 (15) | 0.0005 (14) |
C4 | 0.0382 (18) | 0.0461 (19) | 0.0392 (16) | 0.0067 (14) | −0.0008 (14) | 0.0015 (14) |
C5 | 0.077 (3) | 0.057 (2) | 0.0414 (18) | 0.008 (2) | −0.0172 (19) | 0.0046 (17) |
C6 | 0.070 (3) | 0.063 (3) | 0.067 (2) | 0.018 (2) | −0.018 (2) | 0.018 (2) |
C7 | 0.067 (2) | 0.047 (2) | 0.058 (2) | 0.0143 (18) | −0.0004 (19) | 0.0117 (18) |
C8 | 0.047 (2) | 0.0361 (17) | 0.0466 (18) | 0.0042 (15) | 0.0088 (16) | 0.0007 (15) |
C9 | 0.070 (3) | 0.0391 (18) | 0.0431 (18) | 0.0007 (18) | 0.0051 (18) | 0.0033 (16) |
C11 | 0.0416 (19) | 0.0459 (18) | 0.0411 (17) | −0.0027 (15) | 0.0021 (15) | 0.0022 (15) |
C12 | 0.0320 (16) | 0.0368 (16) | 0.0348 (15) | 0.0039 (13) | 0.0011 (13) | 0.0035 (13) |
C13 | 0.0340 (16) | 0.0345 (15) | 0.0324 (15) | −0.0001 (13) | −0.0031 (13) | 0.0000 (13) |
C14 | 0.0416 (18) | 0.0423 (18) | 0.0401 (17) | −0.0008 (15) | 0.0018 (14) | −0.0026 (14) |
C15 | 0.048 (2) | 0.0512 (19) | 0.0353 (16) | −0.0026 (16) | 0.0084 (15) | 0.0010 (15) |
C16 | 0.056 (2) | 0.0376 (18) | 0.0343 (16) | −0.0083 (16) | 0.0053 (15) | 0.0036 (14) |
C17 | 0.068 (2) | 0.0427 (19) | 0.0341 (16) | 0.0077 (17) | −0.0025 (16) | 0.0008 (15) |
C18 | 0.048 (2) | 0.0390 (18) | 0.0374 (17) | 0.0097 (15) | −0.0080 (16) | −0.0044 (14) |
C19 | 0.046 (2) | 0.0443 (19) | 0.0328 (16) | −0.0012 (16) | −0.0011 (15) | −0.0008 (15) |
C20 | 0.100 (4) | 0.081 (3) | 0.042 (2) | 0.018 (3) | −0.005 (2) | 0.012 (2) |
C21 | 0.091 (3) | 0.062 (3) | 0.093 (3) | 0.035 (3) | 0.001 (3) | 0.015 (2) |
C22 | 0.095 (3) | 0.052 (2) | 0.069 (2) | 0.006 (2) | 0.011 (2) | 0.021 (2) |
C23 | 0.061 (2) | 0.058 (2) | 0.0383 (18) | −0.0153 (19) | 0.0054 (18) | −0.0045 (18) |
C24 | 0.136 (5) | 0.057 (3) | 0.053 (2) | −0.005 (3) | 0.021 (3) | −0.015 (2) |
C25 | 0.0400 (18) | 0.0402 (17) | 0.0328 (15) | 0.0067 (14) | 0.0001 (13) | −0.0017 (13) |
C26 | 0.0374 (18) | 0.062 (2) | 0.050 (2) | −0.0009 (17) | 0.0043 (16) | −0.0174 (19) |
C28 | 0.042 (2) | 0.059 (2) | 0.0361 (17) | −0.0106 (17) | 0.0028 (15) | −0.0047 (15) |
C29 | 0.070 (3) | 0.089 (3) | 0.0279 (16) | −0.030 (2) | 0.0043 (16) | −0.0071 (18) |
C30 | 0.077 (3) | 0.082 (3) | 0.0372 (19) | −0.020 (2) | −0.0132 (19) | 0.0215 (19) |
C31 | 0.057 (2) | 0.061 (2) | 0.0416 (18) | −0.0136 (18) | −0.0032 (17) | 0.0192 (17) |
C32 | 0.0357 (18) | 0.0476 (19) | 0.0355 (16) | −0.0014 (15) | 0.0037 (14) | 0.0045 (14) |
C33 | 0.047 (2) | 0.0493 (19) | 0.0299 (15) | −0.0111 (17) | 0.0080 (15) | 0.0020 (15) |
C35 | 0.0357 (17) | 0.056 (2) | 0.0396 (16) | −0.0025 (16) | 0.0030 (14) | −0.0084 (15) |
C36 | 0.0341 (17) | 0.0466 (19) | 0.0275 (14) | −0.0026 (14) | 0.0019 (13) | −0.0008 (13) |
C37 | 0.0396 (17) | 0.0356 (16) | 0.0283 (14) | 0.0022 (13) | 0.0016 (13) | 0.0023 (13) |
C38 | 0.0423 (19) | 0.0420 (19) | 0.0475 (19) | 0.0059 (15) | 0.0089 (16) | 0.0034 (16) |
C39 | 0.050 (2) | 0.047 (2) | 0.058 (2) | 0.0120 (17) | 0.0213 (18) | 0.0034 (17) |
C40 | 0.050 (2) | 0.045 (2) | 0.051 (2) | −0.0025 (17) | 0.0159 (17) | 0.0020 (16) |
C41 | 0.080 (3) | 0.0402 (19) | 0.0413 (19) | 0.0109 (19) | 0.0048 (18) | 0.0008 (15) |
C42 | 0.061 (2) | 0.0403 (19) | 0.0456 (18) | 0.0118 (17) | −0.0118 (18) | 0.0004 (15) |
C43 | 0.0422 (19) | 0.0413 (19) | 0.0403 (17) | 0.0033 (15) | 0.0008 (15) | 0.0009 (15) |
C44 | 0.121 (4) | 0.073 (3) | 0.056 (2) | 0.013 (3) | 0.010 (3) | 0.021 (2) |
C45 | 0.086 (3) | 0.068 (3) | 0.083 (3) | 0.002 (2) | −0.011 (3) | 0.030 (2) |
C46 | 0.070 (3) | 0.079 (3) | 0.045 (2) | −0.027 (2) | 0.0018 (19) | 0.0154 (19) |
C47 | 0.061 (2) | 0.059 (2) | 0.056 (2) | −0.019 (2) | 0.008 (2) | −0.014 (2) |
C48 | 0.086 (3) | 0.070 (3) | 0.082 (3) | −0.023 (2) | 0.024 (3) | −0.026 (2) |
O1—C2 | 1.193 (4) | C20—H20A | 0.9300 |
O2—C9 | 1.199 (4) | C20—H20B | 0.9300 |
O3—C2 | 1.328 (4) | C21—H21A | 0.9600 |
O3—C4 | 1.447 (4) | C21—H21B | 0.9600 |
O4—C14 | 1.428 (4) | C21—H21C | 0.9600 |
O4—H4A | 0.84 (2) | C22—H22A | 0.9600 |
O5—C18 | 1.201 (4) | C22—H22B | 0.9600 |
O6—C23 | 1.350 (4) | C22—H22C | 0.9600 |
O6—C19 | 1.442 (4) | C23—C24 | 1.487 (6) |
O7—C23 | 1.184 (4) | C24—H24A | 0.9600 |
O10—C9 | 1.348 (5) | C24—H24B | 0.9600 |
O10—C11 | 1.432 (4) | C24—H24C | 0.9600 |
O25—C26 | 1.204 (4) | C25—C26 | 1.507 (5) |
O26—C33 | 1.205 (4) | C25—C42 | 1.544 (4) |
O27—C26 | 1.340 (4) | C25—C43 | 1.544 (5) |
O27—C28 | 1.444 (5) | C25—C37 | 1.581 (4) |
O28—C38 | 1.426 (4) | C28—C29 | 1.501 (5) |
O28—H28A | 0.81 (2) | C28—C36 | 1.526 (4) |
O29—C42 | 1.193 (4) | C28—H28 | 0.976 (18) |
O30—C47 | 1.339 (4) | C29—C30 | 1.509 (6) |
O30—C43 | 1.436 (4) | C29—H29A | 0.9700 |
O31—C47 | 1.185 (5) | C29—H29B | 0.9700 |
O34—C33 | 1.344 (4) | C30—C31 | 1.529 (5) |
O34—C35 | 1.433 (4) | C30—H30A | 0.9700 |
C1—C2 | 1.521 (4) | C30—H30B | 0.9700 |
C1—C19 | 1.534 (5) | C31—C46 | 1.521 (6) |
C1—C18 | 1.540 (4) | C31—C45 | 1.534 (6) |
C1—C13 | 1.578 (4) | C31—C32 | 1.580 (4) |
C4—C5 | 1.511 (5) | C32—C33 | 1.495 (5) |
C4—C12 | 1.530 (4) | C32—C36 | 1.540 (5) |
C4—H4 | 0.9800 | C32—H32 | 0.99 (4) |
C5—C6 | 1.517 (6) | C35—C36 | 1.533 (4) |
C5—H5A | 0.9700 | C35—H35A | 0.9700 |
C5—H5B | 0.9700 | C35—H35B | 0.9700 |
C6—C7 | 1.525 (6) | C36—C37 | 1.544 (4) |
C6—H6A | 0.9700 | C37—C38 | 1.534 (5) |
C6—H6B | 0.9700 | C37—H37 | 0.9800 |
C7—C21 | 1.532 (6) | C38—C39 | 1.526 (5) |
C7—C22 | 1.538 (6) | C38—H38 | 0.95 (3) |
C7—C8 | 1.584 (5) | C39—C40 | 1.546 (5) |
C8—C9 | 1.499 (5) | C39—H39A | 0.9700 |
C8—C12 | 1.546 (4) | C39—H39B | 0.9700 |
C8—H8 | 0.95 (4) | C40—C41 | 1.494 (5) |
C11—C12 | 1.527 (4) | C40—C43 | 1.521 (5) |
C11—H11A | 0.9700 | C40—H40 | 0.95 (4) |
C11—H11B | 0.9700 | C41—C44 | 1.317 (5) |
C12—C13 | 1.553 (4) | C41—C42 | 1.484 (5) |
C13—C14 | 1.532 (4) | C43—H43 | 0.98 (4) |
C13—H13 | 0.9800 | C44—H44A | 0.9300 |
C14—C15 | 1.539 (4) | C44—H44B | 0.9300 |
C14—H14 | 0.9800 | C45—H45A | 0.9600 |
C15—C16 | 1.544 (5) | C45—H45B | 0.9600 |
C15—H15A | 0.9700 | C45—H45C | 0.9600 |
C15—H15B | 0.9700 | C46—H46A | 0.9600 |
C16—C17 | 1.495 (5) | C46—H46B | 0.9600 |
C16—C19 | 1.519 (4) | C46—H46C | 0.9600 |
C16—H16 | 0.9800 | C47—C48 | 1.480 (6) |
C17—C20 | 1.324 (5) | C48—H48A | 0.9600 |
C17—C18 | 1.490 (5) | C48—H48B | 0.9600 |
C19—H19 | 0.952 (18) | C48—H48C | 0.9600 |
C2—O3—C4 | 118.1 (2) | H24A—C24—H24B | 109.5 |
C14—O4—H4A | 105 (3) | C23—C24—H24C | 109.5 |
C23—O6—C19 | 118.0 (3) | H24A—C24—H24C | 109.5 |
C9—O10—C11 | 109.6 (3) | H24B—C24—H24C | 109.5 |
C26—O27—C28 | 117.3 (2) | C26—C25—C42 | 111.2 (3) |
C38—O28—H28A | 116 (3) | C26—C25—C43 | 112.7 (3) |
C47—O30—C43 | 116.4 (3) | C42—C25—C43 | 101.1 (3) |
C33—O34—C35 | 110.1 (2) | C26—C25—C37 | 116.6 (3) |
C2—C1—C19 | 111.6 (2) | C42—C25—C37 | 104.2 (2) |
C2—C1—C18 | 111.6 (3) | C43—C25—C37 | 109.6 (3) |
C19—C1—C18 | 101.1 (3) | O25—C26—O27 | 118.6 (3) |
C2—C1—C13 | 116.8 (2) | O25—C26—C25 | 122.0 (4) |
C19—C1—C13 | 110.5 (2) | O27—C26—C25 | 119.4 (3) |
C18—C1—C13 | 103.8 (2) | O27—C28—C29 | 109.4 (3) |
O1—C2—O3 | 118.4 (3) | O27—C28—C36 | 107.8 (3) |
O1—C2—C1 | 123.1 (3) | C29—C28—C36 | 113.5 (3) |
O3—C2—C1 | 118.5 (3) | O27—C28—H28 | 107 (2) |
O3—C4—C5 | 107.6 (3) | C29—C28—H28 | 111.5 (19) |
O3—C4—C12 | 106.8 (2) | C36—C28—H28 | 107.6 (19) |
C5—C4—C12 | 113.8 (3) | C28—C29—C30 | 108.7 (3) |
O3—C4—H4 | 109.5 | C28—C29—H29A | 109.9 |
C5—C4—H4 | 109.5 | C30—C29—H29A | 109.9 |
C12—C4—H4 | 109.5 | C28—C29—H29B | 109.9 |
C4—C5—C6 | 108.1 (3) | C30—C29—H29B | 109.9 |
C4—C5—H5A | 110.1 | H29A—C29—H29B | 108.3 |
C6—C5—H5A | 110.1 | C29—C30—C31 | 112.8 (3) |
C4—C5—H5B | 110.1 | C29—C30—H30A | 109.0 |
C6—C5—H5B | 110.1 | C31—C30—H30A | 109.0 |
H5A—C5—H5B | 108.4 | C29—C30—H30B | 109.0 |
C5—C6—C7 | 113.4 (3) | C31—C30—H30B | 109.0 |
C5—C6—H6A | 108.9 | H30A—C30—H30B | 107.8 |
C7—C6—H6A | 108.9 | C46—C31—C30 | 110.2 (3) |
C5—C6—H6B | 108.9 | C46—C31—C45 | 108.6 (3) |
C7—C6—H6B | 108.9 | C30—C31—C45 | 108.7 (3) |
H6A—C6—H6B | 107.7 | C46—C31—C32 | 113.8 (3) |
C6—C7—C21 | 109.6 (4) | C30—C31—C32 | 107.8 (3) |
C6—C7—C22 | 110.8 (3) | C45—C31—C32 | 107.6 (3) |
C21—C7—C22 | 107.7 (3) | C33—C32—C36 | 102.4 (3) |
C6—C7—C8 | 108.5 (3) | C33—C32—C31 | 108.9 (3) |
C21—C7—C8 | 107.2 (3) | C36—C32—C31 | 117.4 (3) |
C22—C7—C8 | 113.0 (3) | C33—C32—H32 | 111 (2) |
C9—C8—C12 | 102.2 (3) | C36—C32—H32 | 114 (2) |
C9—C8—C7 | 110.1 (3) | C31—C32—H32 | 103.2 (19) |
C12—C8—C7 | 116.6 (3) | O26—C33—O34 | 120.5 (3) |
C9—C8—H8 | 112 (2) | O26—C33—C32 | 128.8 (3) |
C12—C8—H8 | 106 (2) | O34—C33—C32 | 110.7 (3) |
C7—C8—H8 | 110 (2) | O34—C35—C36 | 105.9 (3) |
O2—C9—O10 | 121.0 (4) | O34—C35—H35A | 110.6 |
O2—C9—C8 | 128.5 (4) | C36—C35—H35A | 110.6 |
O10—C9—C8 | 110.5 (3) | O34—C35—H35B | 110.6 |
O10—C11—C12 | 106.3 (3) | C36—C35—H35B | 110.6 |
O10—C11—H11A | 110.5 | H35A—C35—H35B | 108.7 |
C12—C11—H11A | 110.5 | C28—C36—C35 | 111.8 (3) |
O10—C11—H11B | 110.5 | C28—C36—C32 | 115.9 (3) |
C12—C11—H11B | 110.5 | C35—C36—C32 | 100.7 (3) |
H11A—C11—H11B | 108.7 | C28—C36—C37 | 107.3 (3) |
C11—C12—C4 | 113.0 (3) | C35—C36—C37 | 107.7 (2) |
C11—C12—C8 | 100.0 (3) | C32—C36—C37 | 113.2 (2) |
C4—C12—C8 | 115.7 (3) | C38—C37—C36 | 115.6 (2) |
C11—C12—C13 | 107.5 (2) | C38—C37—C25 | 112.0 (3) |
C4—C12—C13 | 107.8 (2) | C36—C37—C25 | 110.3 (2) |
C8—C12—C13 | 112.6 (2) | C38—C37—H37 | 106.1 |
C14—C13—C12 | 116.6 (2) | C36—C37—H37 | 106.1 |
C14—C13—C1 | 113.2 (2) | C25—C37—H37 | 106.1 |
C12—C13—C1 | 108.4 (2) | O28—C38—C39 | 110.8 (3) |
C14—C13—H13 | 105.9 | O28—C38—C37 | 109.3 (3) |
C12—C13—H13 | 105.9 | C39—C38—C37 | 111.7 (3) |
C1—C13—H13 | 105.9 | O28—C38—H38 | 104.1 (18) |
O4—C14—C13 | 109.3 (2) | C39—C38—H38 | 110.8 (18) |
O4—C14—C15 | 111.8 (3) | C37—C38—H38 | 109.9 (19) |
C13—C14—C15 | 111.9 (3) | C38—C39—C40 | 113.1 (3) |
O4—C14—H14 | 107.9 | C38—C39—H39A | 109.0 |
C13—C14—H14 | 107.9 | C40—C39—H39A | 109.0 |
C15—C14—H14 | 107.9 | C38—C39—H39B | 109.0 |
C14—C15—C16 | 114.0 (2) | C40—C39—H39B | 109.0 |
C14—C15—H15A | 108.7 | H39A—C39—H39B | 107.8 |
C16—C15—H15A | 108.7 | C41—C40—C43 | 102.1 (3) |
C14—C15—H15B | 108.7 | C41—C40—C39 | 111.5 (3) |
C16—C15—H15B | 108.7 | C43—C40—C39 | 108.4 (3) |
H15A—C15—H15B | 107.6 | C41—C40—H40 | 113 (2) |
C17—C16—C19 | 101.9 (3) | C43—C40—H40 | 109 (2) |
C17—C16—C15 | 111.2 (3) | C39—C40—H40 | 112 (2) |
C19—C16—C15 | 109.3 (3) | C44—C41—C42 | 122.4 (4) |
C17—C16—H16 | 111.3 | C44—C41—C40 | 128.9 (4) |
C19—C16—H16 | 111.3 | C42—C41—C40 | 108.7 (3) |
C15—C16—H16 | 111.3 | O29—C42—C41 | 128.6 (3) |
C20—C17—C18 | 122.9 (4) | O29—C42—C25 | 126.0 (4) |
C20—C17—C16 | 129.3 (4) | C41—C42—C25 | 105.3 (3) |
C18—C17—C16 | 107.8 (3) | O30—C43—C40 | 107.4 (3) |
O5—C18—C17 | 128.2 (3) | O30—C43—C25 | 109.3 (3) |
O5—C18—C1 | 125.9 (3) | C40—C43—C25 | 101.5 (3) |
C17—C18—C1 | 105.7 (3) | O30—C43—H43 | 112 (2) |
O6—C19—C16 | 106.9 (3) | C40—C43—H43 | 116 (2) |
O6—C19—C1 | 109.9 (3) | C25—C43—H43 | 111 (2) |
C16—C19—C1 | 101.6 (2) | C41—C44—H44A | 120.0 |
O6—C19—H19 | 112.0 (18) | C41—C44—H44B | 120.0 |
C16—C19—H19 | 110.5 (17) | H44A—C44—H44B | 120.0 |
C1—C19—H19 | 115.1 (18) | C31—C45—H45A | 109.5 |
C17—C20—H20A | 120.0 | C31—C45—H45B | 109.5 |
C17—C20—H20B | 120.0 | H45A—C45—H45B | 109.5 |
H20A—C20—H20B | 120.0 | C31—C45—H45C | 109.5 |
C7—C21—H21A | 109.5 | H45A—C45—H45C | 109.5 |
C7—C21—H21B | 109.5 | H45B—C45—H45C | 109.5 |
H21A—C21—H21B | 109.5 | C31—C46—H46A | 109.5 |
C7—C21—H21C | 109.5 | C31—C46—H46B | 109.5 |
H21A—C21—H21C | 109.5 | H46A—C46—H46B | 109.5 |
H21B—C21—H21C | 109.5 | C31—C46—H46C | 109.5 |
C7—C22—H22A | 109.5 | H46A—C46—H46C | 109.5 |
C7—C22—H22B | 109.5 | H46B—C46—H46C | 109.5 |
H22A—C22—H22B | 109.5 | O31—C47—O30 | 123.1 (4) |
C7—C22—H22C | 109.5 | O31—C47—C48 | 126.2 (4) |
H22A—C22—H22C | 109.5 | O30—C47—C48 | 110.6 (4) |
H22B—C22—H22C | 109.5 | C47—C48—H48A | 109.5 |
O7—C23—O6 | 123.2 (4) | C47—C48—H48B | 109.5 |
O7—C23—C24 | 126.0 (4) | H48A—C48—H48B | 109.5 |
O6—C23—C24 | 110.8 (4) | C47—C48—H48C | 109.5 |
C23—C24—H24A | 109.5 | H48A—C48—H48C | 109.5 |
C23—C24—H24B | 109.5 | H48B—C48—H48C | 109.5 |
C4—O3—C2—O1 | 178.7 (3) | C28—O27—C26—O25 | −176.7 (3) |
C4—O3—C2—C1 | −2.7 (4) | C28—O27—C26—C25 | 2.3 (4) |
C19—C1—C2—O1 | 82.7 (4) | C42—C25—C26—O25 | −33.7 (4) |
C18—C1—C2—O1 | −29.7 (4) | C43—C25—C26—O25 | 79.1 (4) |
C13—C1—C2—O1 | −148.8 (3) | C37—C25—C26—O25 | −153.0 (3) |
C19—C1—C2—O3 | −95.8 (3) | C42—C25—C26—O27 | 147.3 (3) |
C18—C1—C2—O3 | 151.8 (3) | C43—C25—C26—O27 | −100.0 (3) |
C13—C1—C2—O3 | 32.7 (4) | C37—C25—C26—O27 | 28.0 (4) |
C2—O3—C4—C5 | −172.3 (3) | C26—O27—C28—C29 | −176.6 (3) |
C2—O3—C4—C12 | −49.7 (4) | C26—O27—C28—C36 | −52.7 (4) |
O3—C4—C5—C6 | 174.1 (3) | O27—C28—C29—C30 | 176.1 (3) |
C12—C4—C5—C6 | 55.9 (4) | C36—C28—C29—C30 | 55.7 (4) |
C4—C5—C6—C7 | −66.5 (4) | C28—C29—C30—C31 | −67.8 (4) |
C5—C6—C7—C21 | 173.7 (3) | C29—C30—C31—C46 | −67.3 (4) |
C5—C6—C7—C22 | −67.6 (4) | C29—C30—C31—C45 | 173.8 (3) |
C5—C6—C7—C8 | 57.0 (4) | C29—C30—C31—C32 | 57.5 (4) |
C6—C7—C8—C9 | −155.1 (3) | C46—C31—C32—C33 | −32.0 (4) |
C21—C7—C8—C9 | 86.7 (4) | C30—C31—C32—C33 | −154.5 (3) |
C22—C7—C8—C9 | −31.8 (4) | C45—C31—C32—C33 | 88.4 (4) |
C6—C7—C8—C12 | −39.3 (4) | C46—C31—C32—C36 | 83.7 (4) |
C21—C7—C8—C12 | −157.5 (3) | C30—C31—C32—C36 | −38.9 (4) |
C22—C7—C8—C12 | 84.0 (4) | C45—C31—C32—C36 | −155.9 (3) |
C11—O10—C9—O2 | −178.0 (3) | C35—O34—C33—O26 | 179.9 (3) |
C11—O10—C9—C8 | 1.9 (4) | C35—O34—C33—C32 | 1.7 (3) |
C12—C8—C9—O2 | 157.8 (3) | C36—C32—C33—O26 | 161.1 (3) |
C7—C8—C9—O2 | −77.6 (4) | C31—C32—C33—O26 | −73.9 (4) |
C12—C8—C9—O10 | −22.1 (3) | C36—C32—C33—O34 | −20.9 (3) |
C7—C8—C9—O10 | 102.5 (3) | C31—C32—C33—O34 | 104.1 (3) |
C9—O10—C11—C12 | 19.7 (3) | C33—O34—C35—C36 | 18.6 (3) |
O10—C11—C12—C4 | −155.2 (2) | O27—C28—C36—C35 | −45.8 (3) |
O10—C11—C12—C8 | −31.6 (3) | C29—C28—C36—C35 | 75.6 (4) |
O10—C11—C12—C13 | 86.0 (3) | O27—C28—C36—C32 | −160.4 (3) |
O3—C4—C12—C11 | −45.2 (3) | C29—C28—C36—C32 | −39.1 (4) |
C5—C4—C12—C11 | 73.4 (4) | O27—C28—C36—C37 | 72.1 (3) |
O3—C4—C12—C8 | −159.7 (3) | C29—C28—C36—C37 | −166.6 (3) |
C5—C4—C12—C8 | −41.0 (4) | O34—C35—C36—C28 | −153.6 (3) |
O3—C4—C12—C13 | 73.4 (3) | O34—C35—C36—C32 | −29.9 (3) |
C5—C4—C12—C13 | −168.0 (3) | O34—C35—C36—C37 | 88.8 (3) |
C9—C8—C12—C11 | 31.3 (3) | C33—C32—C36—C28 | 150.4 (3) |
C7—C8—C12—C11 | −88.9 (3) | C31—C32—C36—C28 | 31.3 (4) |
C9—C8—C12—C4 | 152.9 (3) | C33—C32—C36—C35 | 29.6 (3) |
C7—C8—C12—C4 | 32.8 (4) | C31—C32—C36—C35 | −89.5 (3) |
C9—C8—C12—C13 | −82.5 (3) | C33—C32—C36—C37 | −85.0 (3) |
C7—C8—C12—C13 | 157.3 (3) | C31—C32—C36—C37 | 155.8 (3) |
C11—C12—C13—C14 | −151.4 (3) | C28—C36—C37—C38 | 87.4 (3) |
C4—C12—C13—C14 | 86.5 (3) | C35—C36—C37—C38 | −152.1 (3) |
C8—C12—C13—C14 | −42.2 (4) | C32—C36—C37—C38 | −41.7 (4) |
C11—C12—C13—C1 | 79.4 (3) | C28—C36—C37—C25 | −40.9 (3) |
C4—C12—C13—C1 | −42.6 (3) | C35—C36—C37—C25 | 79.6 (3) |
C8—C12—C13—C1 | −171.4 (3) | C32—C36—C37—C25 | −170.0 (3) |
C2—C1—C13—C14 | −137.5 (3) | C26—C25—C37—C38 | −135.5 (3) |
C19—C1—C13—C14 | −8.4 (3) | C42—C25—C37—C38 | 101.5 (3) |
C18—C1—C13—C14 | 99.3 (3) | C43—C25—C37—C38 | −6.1 (3) |
C2—C1—C13—C12 | −6.4 (3) | C26—C25—C37—C36 | −5.3 (4) |
C19—C1—C13—C12 | 122.6 (3) | C42—C25—C37—C36 | −128.3 (3) |
C18—C1—C13—C12 | −129.7 (3) | C43—C25—C37—C36 | 124.1 (3) |
C12—C13—C14—O4 | −46.0 (4) | C36—C37—C38—O28 | −52.3 (4) |
C1—C13—C14—O4 | 80.9 (3) | C25—C37—C38—O28 | 75.1 (3) |
C12—C13—C14—C15 | −170.3 (2) | C36—C37—C38—C39 | −175.2 (3) |
C1—C13—C14—C15 | −43.5 (3) | C25—C37—C38—C39 | −47.8 (4) |
O4—C14—C15—C16 | −86.0 (3) | O28—C38—C39—C40 | −81.6 (4) |
C13—C14—C15—C16 | 37.0 (4) | C37—C38—C39—C40 | 40.5 (4) |
C14—C15—C16—C17 | −90.0 (3) | C38—C39—C40—C41 | −90.6 (4) |
C14—C15—C16—C19 | 21.8 (4) | C38—C39—C40—C43 | 21.0 (4) |
C19—C16—C17—C20 | 152.3 (4) | C43—C40—C41—C44 | 155.4 (4) |
C15—C16—C17—C20 | −91.3 (4) | C39—C40—C41—C44 | −89.1 (5) |
C19—C16—C17—C18 | −28.4 (3) | C43—C40—C41—C42 | −26.6 (4) |
C15—C16—C17—C18 | 88.1 (3) | C39—C40—C41—C42 | 88.9 (3) |
C20—C17—C18—O5 | 4.3 (6) | C44—C41—C42—O29 | 0.5 (6) |
C16—C17—C18—O5 | −175.1 (3) | C40—C41—C42—O29 | −177.6 (4) |
C20—C17—C18—C1 | −179.7 (3) | C44—C41—C42—C25 | 177.1 (4) |
C16—C17—C18—C1 | 0.9 (3) | C40—C41—C42—C25 | −1.0 (4) |
C2—C1—C18—O5 | −38.6 (4) | C26—C25—C42—O29 | −35.7 (5) |
C19—C1—C18—O5 | −157.4 (3) | C43—C25—C42—O29 | −155.6 (4) |
C13—C1—C18—O5 | 88.0 (4) | C37—C25—C42—O29 | 90.7 (4) |
C2—C1—C18—C17 | 145.3 (3) | C26—C25—C42—C41 | 147.6 (3) |
C19—C1—C18—C17 | 26.5 (3) | C43—C25—C42—C41 | 27.7 (3) |
C13—C1—C18—C17 | −88.1 (3) | C37—C25—C42—C41 | −86.0 (3) |
C23—O6—C19—C16 | −153.8 (3) | C47—O30—C43—C40 | −153.7 (3) |
C23—O6—C19—C1 | 96.7 (3) | C47—O30—C43—C25 | 97.0 (3) |
C17—C16—C19—O6 | −70.5 (3) | C41—C40—C43—O30 | −71.2 (3) |
C15—C16—C19—O6 | 171.7 (3) | C39—C40—C43—O30 | 171.1 (3) |
C17—C16—C19—C1 | 44.7 (3) | C41—C40—C43—C25 | 43.4 (3) |
C15—C16—C19—C1 | −73.1 (3) | C39—C40—C43—C25 | −74.3 (3) |
C2—C1—C19—O6 | −49.6 (3) | C26—C25—C43—O30 | −49.4 (3) |
C18—C1—C19—O6 | 69.2 (3) | C42—C25—C43—O30 | 69.4 (3) |
C13—C1—C19—O6 | 178.6 (2) | C37—C25—C43—O30 | 179.0 (2) |
C2—C1—C19—C16 | −162.6 (3) | C26—C25—C43—C40 | −162.6 (3) |
C18—C1—C19—C16 | −43.8 (3) | C42—C25—C43—C40 | −43.8 (3) |
C13—C1—C19—C16 | 65.7 (3) | C37—C25—C43—C40 | 65.8 (3) |
C19—O6—C23—O7 | 1.1 (5) | C43—O30—C47—O31 | 1.2 (6) |
C19—O6—C23—C24 | −178.7 (3) | C43—O30—C47—C48 | −176.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O28—H28A···O1i | 0.81 (2) | 1.93 (2) | 2.711 (3) | 161 (4) |
O4—H4A···O26 | 0.84 (2) | 2.20 (3) | 2.957 (4) | 150 (4) |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C22H26O8 |
Mr | 418.43 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 12.0055 (11), 13.5835 (13), 25.027 (2) |
V (Å3) | 4081.3 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.49 × 0.43 × 0.32 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.744, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24111, 4945, 3810 |
Rint | 0.130 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.115, 1.00 |
No. of reflections | 4945 |
No. of parameters | 583 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.18 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O28—H28A···O1i | 0.81 (2) | 1.93 (2) | 2.711 (3) | 161 (4) |
O4—H4A···O26 | 0.84 (2) | 2.20 (3) | 2.957 (4) | 150 (4) |
Symmetry code: (i) x+1, y, z. |
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Since the natural diterpenoid Macrocalyxin J exhibits cytotoxicity in vitro against cultures of Hela cells and the IC50 =31.597µg/ml (Shi et al., 2007), we have derived the title compound from it.
The crystal packing is shown in Fig. 3. Two unique molecules are present in the asymmetric unit, both molecule 1 (Fig.1) and molecule 2 (Fig.2) are built up from five fused rings, three six membered and two five membered rings. Some geometrical features of these rings were investigated using PLATON (Spek, 2003).
For the molecule 1, cyclohexane ring A (C4—C8/C12) adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.5295 (42) Å, and θ= 157.69 (43) and φ = 271.5 (11) °, ring B (O3/C2/C1/C13/C12/C4) exists in a screw-boat conformation (Q = 0.6672 (33) Å, θ = 108.66 (28) and φ = 92.0 (3) °), ring C (C1/C13—C16/C19) adopt the boat conformation (Q = 0.8109 (35) Å, θ = 79.21 (24) and φ = 294.2 (2) °). The two five-membered rings, ring D (C1/C18/C17/C16/C19) adopts an envelope conformation with puckering parameters Q2 = 0.4565 (34) Å, and φ2 = 143.6 (4)° (envelope on C19), the ring E (O10/C9/C8/C12/C11) adopts an envelope conformation with puckering parameters Q2 = 0.3341 (36) Å, and φ2 = 284.7 (6)° (envelope on C12).
For the molecule 2, cyclohexane ring A' (C28—C32/C36) adopts a chair conformation with puckering parameters Q = 0.5312 (40) Å, and θ= 156.14 (41) and φ =274.4 (10) °, ring B' (O27/C26/C25/C37/C36/C28) exists in a screw-boat conformation (Q = 0.6421 (36) Å, and θ= 110.70 (31) and φ =94.7 (3) °), ring C' (C25/C37—C40/C43) adopt the boat conformation (Q = 0.8400 (37) Å, θ = 80.52 (25) and φ = 293.6 (3)°). The two five-membered rings, ring D' (C25/C42/C41/C40/C43) adopts an envelope conformation with puckering parameters Q2 = 0.4526 (38) Å, and φ2 = 146.0 (5)° (envelope on C43), the ring E' (O34/C33/C32/C36/C35) adopts an envelope conformation with puckering parameters Q2 = 0.3156 (35) Å, and φ2 = 284.8 (6) ° (envelope on C36).
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.