Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104024291/gd1348sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104024291/gd1348Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104024291/gd1348IIsup3.hkl |
CCDC references: 257029; 257030
Acetone extractions were obtained from dried roots of H. candicans WALL., and (I) was purified by column chromatography as described previously (Xiao et al., 1997). HR-EIMS m/z: 572.1681 [M]+ (calculated for C32H28O10: 572.1683); 1H NMR (CDCl3): δH 7.76 (2H,d, J = 9.6 Hz, C5/25—H), 7.69 (2H, d, J = 2.1 Hz, C11/31—H), 7.37 (2H, s, C7/27—H), 6.82 (2H, d, J = 2.1 Hz, C10/30—H), 6.36 (2H, d, J = 9.6 Hz, C4/24—H), 4.49 (2H, dd, J = 11.0 and 7.3 Hz, C13/33—Ha), 4.43 (2H, dd, J = 11.0 and 3.9 Hz, C13/33—Hb), 3.99 (2H, dd, J = 7.3 and 3.9 Hz, C14/34—H), 1.14 (12H, s, C16/36—H3 and C17/37—H3). Compound (I) (10 mg) was dissolved in either DMSO or DMF (0.1–0.2 ml), after which water (approximately 0.02 ml) was added to each solution. Crystals with different crystal forms grew from the two solutions over a period of about a week.
A full-sphere data set was collected for the DMSO form to aid in the determination of the absolute configuration of the structure. A full-sphere data set was also collected for the DMF form, but Friedel pairs were merged in the refinement because of the absence of significant anomalous scattering effects. The absolute configuration of the DMF form was assumed from that of the DMSO form. H atoms were placed at calculated positions [C—H = 0.95–1.00 Å, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(parent atom) for all other atoms] and were included in the structure-factor calculation as riding.
For both compounds, data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001).
C32H28O10·2C2H6OS | Dx = 1.392 Mg m−3 |
Mr = 728.80 | Melting point = 364–370 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5833 reflections |
a = 10.903 (2) Å | θ = 2.3–28.2° |
b = 13.068 (2) Å | µ = 0.22 mm−1 |
c = 24.400 (4) Å | T = 200 K |
V = 3476.5 (11) Å3 | Needle, colourless |
Z = 4 | 0.50 × 0.20 × 0.04 mm |
F(000) = 1536 |
Bruker SMART APEX CCD area-detector diffractometer | 7659 independent reflections |
Radiation source: MacScience, M18XCE rotating anode | 7041 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.1°, θmin = 2.1° |
ω scan | h = −13→13 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −16→16 |
Tmin = 0.913, Tmax = 1.0 | l = −31→31 |
30564 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0729P)2 + 0.5601P] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max = 0.003 |
7659 reflections | Δρmax = 0.40 e Å−3 |
498 parameters | Δρmin = −0.19 e Å−3 |
18 restraints | Absolute structure: Flack (1983), 3379 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (6) |
C32H28O10·2C2H6OS | V = 3476.5 (11) Å3 |
Mr = 728.80 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.903 (2) Å | µ = 0.22 mm−1 |
b = 13.068 (2) Å | T = 200 K |
c = 24.400 (4) Å | 0.50 × 0.20 × 0.04 mm |
Bruker SMART APEX CCD area-detector diffractometer | 7659 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 7041 reflections with I > 2σ(I) |
Tmin = 0.913, Tmax = 1.0 | Rint = 0.026 |
30564 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.099 | Δρmax = 0.40 e Å−3 |
S = 0.90 | Δρmin = −0.19 e Å−3 |
7659 reflections | Absolute structure: Flack (1983), 3379 Friedel pairs |
498 parameters | Absolute structure parameter: 0.04 (6) |
18 restraints |
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 | Occ. (<1) | |
S1A | 0.15725 (5) | 0.81176 (4) | 0.466258 (17) | 0.04392 (12) | |
O1A | 0.1606 (2) | 0.74413 (11) | 0.51541 (5) | 0.0664 (5) | |
C1A | 0.2781 (3) | 0.9002 (2) | 0.47354 (12) | 0.0763 (8) | |
H11A | 0.2691 | 0.9369 | 0.5083 | 0.114* | |
H12A | 0.2759 | 0.9491 | 0.4431 | 0.114* | |
H13A | 0.3567 | 0.8637 | 0.4732 | 0.114* | |
C2A | 0.0334 (3) | 0.8963 (2) | 0.47584 (11) | 0.0701 (7) | |
H21A | −0.0434 | 0.8573 | 0.4771 | 0.105* | |
H22A | 0.0304 | 0.9451 | 0.4454 | 0.105* | |
H23A | 0.0442 | 0.9335 | 0.5104 | 0.105* | |
S1B | 0.71444 (19) | 0.41444 (9) | 0.36750 (4) | 0.0511 (5) | 0.551 (3) |
O1B | 0.7189 (5) | 0.4712 (3) | 0.42049 (14) | 0.0912 (15) | 0.551 (3) |
C1B | 0.6009 (6) | 0.3191 (6) | 0.3757 (4) | 0.077 (3) | 0.551 (3) |
H11B | 0.6178 | 0.2796 | 0.4090 | 0.115* | 0.551 (3) |
H12B | 0.6017 | 0.2734 | 0.3439 | 0.115* | 0.551 (3) |
H13B | 0.5201 | 0.3516 | 0.3788 | 0.115* | 0.551 (3) |
C2B | 0.8404 (4) | 0.3288 (4) | 0.36807 (17) | 0.0552 (10) | 0.551 (3) |
H21B | 0.9167 | 0.3675 | 0.3725 | 0.083* | 0.551 (3) |
H22B | 0.8428 | 0.2909 | 0.3334 | 0.083* | 0.551 (3) |
H23B | 0.8313 | 0.2806 | 0.3986 | 0.083* | 0.551 (3) |
S1C | 0.6283 (2) | 0.41609 (10) | 0.36918 (5) | 0.0526 (6) | 0.449 (3) |
O1C | 0.5890 (5) | 0.4601 (4) | 0.42268 (18) | 0.0869 (16) | 0.449 (3) |
C1C | 0.6093 (8) | 0.2823 (4) | 0.3740 (5) | 0.0458 (17) | 0.449 (3) |
H11C | 0.6435 | 0.2581 | 0.4088 | 0.069* | 0.449 (3) |
H12C | 0.6521 | 0.2490 | 0.3435 | 0.069* | 0.449 (3) |
H13C | 0.5218 | 0.2655 | 0.3724 | 0.069* | 0.449 (3) |
C2C | 0.7900 (6) | 0.4183 (7) | 0.3690 (3) | 0.090 (3) | 0.449 (3) |
H21C | 0.8185 | 0.4894 | 0.3695 | 0.136* | 0.449 (3) |
H22C | 0.8204 | 0.3843 | 0.3358 | 0.136* | 0.449 (3) |
H23C | 0.8209 | 0.3825 | 0.4014 | 0.136* | 0.449 (3) |
C1 | 0.28323 (16) | 0.27607 (12) | 0.25822 (6) | 0.0277 (3) | |
C2 | 0.38609 (15) | 0.26870 (12) | 0.22505 (6) | 0.0287 (3) | |
O2 | 0.49653 (11) | 0.28602 (9) | 0.25005 (5) | 0.0322 (2) | |
C3 | 0.60495 (16) | 0.28647 (14) | 0.22135 (7) | 0.0373 (4) | |
O3 | 0.69646 (12) | 0.30371 (13) | 0.24724 (6) | 0.0496 (3) | |
C4 | 0.59840 (18) | 0.26553 (18) | 0.16344 (8) | 0.0464 (5) | |
H4 | 0.6718 | 0.2652 | 0.1425 | 0.056* | |
C5 | 0.4927 (2) | 0.24669 (18) | 0.13870 (7) | 0.0473 (5) | |
H5 | 0.4920 | 0.2324 | 0.1005 | 0.057* | |
C6 | 0.37874 (17) | 0.24752 (14) | 0.16863 (7) | 0.0352 (4) | |
C7 | 0.26555 (18) | 0.23256 (16) | 0.14385 (7) | 0.0391 (4) | |
H7 | 0.2599 | 0.2179 | 0.1058 | 0.047* | |
C8 | 0.16150 (17) | 0.23944 (13) | 0.17579 (6) | 0.0342 (3) | |
C9 | 0.17246 (16) | 0.26063 (12) | 0.23197 (6) | 0.0300 (3) | |
O9 | 0.05933 (11) | 0.26830 (10) | 0.25545 (5) | 0.0353 (3) | |
C10 | 0.03164 (18) | 0.23526 (15) | 0.16574 (8) | 0.0403 (4) | |
H10 | −0.0072 | 0.2222 | 0.1316 | 0.048* | |
C11 | −0.02381 (17) | 0.25333 (15) | 0.21355 (8) | 0.0410 (4) | |
H11 | −0.1103 | 0.2556 | 0.2182 | 0.049* | |
O12 | 0.29792 (10) | 0.30942 (9) | 0.31078 (4) | 0.0320 (2) | |
C13 | 0.23055 (16) | 0.25640 (13) | 0.35269 (6) | 0.0303 (3) | |
H131 | 0.2634 | 0.1864 | 0.3577 | 0.036* | |
H132 | 0.1428 | 0.2513 | 0.3426 | 0.036* | |
C14 | 0.24521 (14) | 0.31749 (12) | 0.40457 (6) | 0.0267 (3) | |
H14 | 0.3309 | 0.3446 | 0.4062 | 0.032* | |
O14 | 0.16269 (11) | 0.40120 (8) | 0.40189 (4) | 0.0299 (2) | |
C15 | 0.22031 (15) | 0.25426 (12) | 0.45664 (6) | 0.0283 (3) | |
C16 | 0.10797 (17) | 0.18687 (15) | 0.45113 (7) | 0.0373 (4) | |
H161 | 0.0880 | 0.1569 | 0.4868 | 0.056* | |
H162 | 0.1246 | 0.1321 | 0.4247 | 0.056* | |
H163 | 0.0386 | 0.2280 | 0.4382 | 0.056* | |
C17 | 0.33305 (18) | 0.19297 (15) | 0.47204 (7) | 0.0404 (4) | |
H171 | 0.4005 | 0.2398 | 0.4808 | 0.061* | |
H172 | 0.3568 | 0.1492 | 0.4412 | 0.061* | |
H173 | 0.3148 | 0.1503 | 0.5041 | 0.061* | |
C21 | 0.28214 (16) | 0.45849 (13) | 0.64109 (6) | 0.0313 (3) | |
C22 | 0.38356 (16) | 0.47089 (12) | 0.67462 (6) | 0.0302 (3) | |
O22 | 0.49513 (11) | 0.47459 (9) | 0.64862 (5) | 0.0347 (3) | |
C23 | 0.60127 (16) | 0.49270 (14) | 0.67658 (8) | 0.0359 (4) | |
O23 | 0.69212 (13) | 0.50192 (12) | 0.64861 (6) | 0.0485 (3) | |
C24 | 0.59438 (19) | 0.49833 (15) | 0.73522 (8) | 0.0428 (4) | |
H24 | 0.6677 | 0.5061 | 0.7559 | 0.051* | |
C25 | 0.48830 (19) | 0.49288 (15) | 0.76109 (7) | 0.0413 (4) | |
H25 | 0.4868 | 0.4975 | 0.7999 | 0.050* | |
C26 | 0.37580 (17) | 0.48017 (13) | 0.73208 (7) | 0.0345 (4) | |
C27 | 0.26182 (18) | 0.47888 (13) | 0.75740 (7) | 0.0380 (4) | |
H27 | 0.2553 | 0.4836 | 0.7961 | 0.046* | |
C28 | 0.15850 (18) | 0.47058 (12) | 0.72541 (7) | 0.0361 (4) | |
C29 | 0.16994 (17) | 0.46045 (12) | 0.66848 (7) | 0.0336 (3) | |
O29 | 0.05678 (12) | 0.45435 (11) | 0.64468 (5) | 0.0425 (3) | |
C30 | 0.0273 (2) | 0.47100 (15) | 0.73589 (8) | 0.0443 (4) | |
H30 | −0.0121 | 0.4768 | 0.7705 | 0.053* | |
C31 | −0.02691 (18) | 0.46159 (16) | 0.68680 (9) | 0.0456 (5) | |
H31 | −0.1133 | 0.4601 | 0.6817 | 0.055* | |
O32 | 0.30184 (11) | 0.43987 (11) | 0.58701 (5) | 0.0398 (3) | |
C33 | 0.21704 (16) | 0.48007 (14) | 0.54730 (6) | 0.0330 (3) | |
H331 | 0.2304 | 0.5544 | 0.5421 | 0.040* | |
H332 | 0.1315 | 0.4691 | 0.5596 | 0.040* | |
O34 | 0.19016 (11) | 0.32413 (9) | 0.50049 (4) | 0.0319 (2) | |
C34 | 0.24087 (14) | 0.42313 (12) | 0.49440 (6) | 0.0277 (3) | |
H34 | 0.3314 | 0.4170 | 0.4887 | 0.033* | |
C35 | 0.18294 (15) | 0.47675 (12) | 0.44404 (6) | 0.0282 (3) | |
C36 | 0.05642 (16) | 0.51938 (14) | 0.45609 (7) | 0.0355 (4) | |
H361 | 0.0177 | 0.5413 | 0.4218 | 0.053* | |
H362 | 0.0637 | 0.5781 | 0.4809 | 0.053* | |
H363 | 0.0061 | 0.4663 | 0.4734 | 0.053* | |
C37 | 0.26861 (17) | 0.55843 (14) | 0.42164 (7) | 0.0369 (4) | |
H371 | 0.3461 | 0.5267 | 0.4104 | 0.055* | |
H372 | 0.2846 | 0.6096 | 0.4501 | 0.055* | |
H373 | 0.2303 | 0.5917 | 0.3900 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0686 (3) | 0.0378 (2) | 0.02539 (19) | 0.0028 (2) | −0.0078 (2) | −0.00343 (17) |
O1A | 0.1260 (15) | 0.0388 (7) | 0.0344 (7) | 0.0006 (9) | −0.0159 (9) | 0.0014 (6) |
C1A | 0.088 (2) | 0.0812 (18) | 0.0595 (16) | −0.0246 (15) | −0.0151 (14) | 0.0018 (14) |
C2A | 0.0829 (18) | 0.0684 (15) | 0.0589 (15) | 0.0225 (14) | 0.0168 (13) | 0.0131 (12) |
S1B | 0.0635 (12) | 0.0597 (7) | 0.0303 (5) | 0.0111 (7) | −0.0022 (6) | 0.0011 (4) |
O1B | 0.151 (4) | 0.074 (2) | 0.0493 (19) | 0.023 (3) | 0.000 (2) | −0.0120 (17) |
C1B | 0.059 (4) | 0.125 (8) | 0.047 (3) | −0.026 (5) | 0.002 (3) | 0.001 (6) |
C2B | 0.047 (2) | 0.072 (3) | 0.047 (2) | −0.003 (2) | −0.0007 (17) | −0.0059 (19) |
S1C | 0.0773 (16) | 0.0458 (7) | 0.0347 (6) | 0.0054 (7) | −0.0110 (6) | 0.0009 (5) |
O1C | 0.125 (5) | 0.073 (3) | 0.063 (3) | 0.016 (3) | 0.000 (3) | −0.019 (2) |
C1C | 0.055 (4) | 0.038 (3) | 0.045 (3) | −0.002 (2) | 0.005 (3) | 0.002 (3) |
C2C | 0.088 (6) | 0.140 (8) | 0.043 (3) | −0.043 (6) | −0.003 (4) | 0.009 (4) |
C1 | 0.0367 (8) | 0.0292 (7) | 0.0173 (6) | 0.0022 (6) | 0.0011 (6) | −0.0014 (5) |
C2 | 0.0343 (8) | 0.0304 (7) | 0.0215 (7) | 0.0003 (6) | −0.0003 (6) | −0.0006 (6) |
O2 | 0.0329 (6) | 0.0400 (6) | 0.0238 (5) | 0.0003 (5) | 0.0030 (4) | −0.0018 (4) |
C3 | 0.0337 (9) | 0.0429 (9) | 0.0353 (9) | 0.0015 (7) | 0.0060 (7) | −0.0008 (7) |
O3 | 0.0342 (7) | 0.0709 (9) | 0.0438 (7) | −0.0011 (7) | 0.0026 (6) | −0.0028 (7) |
C4 | 0.0395 (10) | 0.0660 (13) | 0.0338 (9) | 0.0025 (9) | 0.0131 (8) | −0.0061 (9) |
C5 | 0.0501 (11) | 0.0657 (12) | 0.0262 (9) | 0.0027 (10) | 0.0103 (8) | −0.0093 (8) |
C6 | 0.0423 (9) | 0.0421 (9) | 0.0211 (7) | 0.0027 (7) | 0.0066 (7) | −0.0044 (7) |
C7 | 0.0490 (10) | 0.0501 (10) | 0.0182 (7) | −0.0006 (8) | −0.0001 (7) | −0.0050 (7) |
C8 | 0.0427 (9) | 0.0365 (8) | 0.0235 (7) | 0.0013 (7) | −0.0058 (7) | −0.0015 (6) |
C9 | 0.0353 (8) | 0.0318 (7) | 0.0230 (7) | 0.0042 (7) | 0.0022 (6) | −0.0007 (6) |
O9 | 0.0312 (6) | 0.0453 (7) | 0.0294 (6) | 0.0031 (5) | 0.0004 (5) | −0.0033 (5) |
C10 | 0.0445 (10) | 0.0457 (10) | 0.0305 (8) | −0.0008 (8) | −0.0099 (7) | −0.0005 (7) |
C11 | 0.0331 (9) | 0.0475 (10) | 0.0425 (10) | 0.0032 (8) | −0.0078 (7) | 0.0008 (8) |
O12 | 0.0381 (6) | 0.0401 (6) | 0.0177 (5) | −0.0059 (5) | 0.0030 (4) | −0.0042 (4) |
C13 | 0.0405 (9) | 0.0330 (8) | 0.0176 (6) | −0.0025 (7) | 0.0020 (6) | −0.0019 (6) |
C14 | 0.0314 (7) | 0.0311 (7) | 0.0175 (6) | −0.0002 (6) | 0.0001 (5) | −0.0025 (6) |
O14 | 0.0370 (6) | 0.0330 (5) | 0.0196 (5) | 0.0033 (5) | −0.0042 (4) | −0.0039 (4) |
C15 | 0.0384 (8) | 0.0300 (7) | 0.0166 (7) | 0.0010 (6) | 0.0001 (6) | −0.0016 (6) |
C16 | 0.0486 (10) | 0.0383 (9) | 0.0251 (8) | −0.0094 (8) | 0.0052 (7) | −0.0025 (7) |
C17 | 0.0503 (10) | 0.0430 (9) | 0.0281 (8) | 0.0096 (9) | −0.0033 (7) | 0.0010 (7) |
C21 | 0.0389 (9) | 0.0323 (8) | 0.0227 (7) | 0.0042 (7) | 0.0007 (6) | −0.0068 (6) |
C22 | 0.0375 (8) | 0.0283 (8) | 0.0248 (8) | 0.0017 (6) | −0.0004 (6) | −0.0039 (6) |
O22 | 0.0370 (6) | 0.0425 (7) | 0.0248 (5) | 0.0015 (5) | −0.0025 (5) | −0.0072 (5) |
C23 | 0.0323 (9) | 0.0348 (9) | 0.0407 (10) | 0.0021 (7) | −0.0029 (7) | −0.0053 (7) |
O23 | 0.0374 (7) | 0.0582 (8) | 0.0498 (8) | −0.0016 (6) | −0.0018 (6) | −0.0084 (6) |
C24 | 0.0507 (11) | 0.0441 (10) | 0.0337 (9) | −0.0014 (8) | −0.0142 (8) | −0.0045 (7) |
C25 | 0.0544 (11) | 0.0429 (10) | 0.0266 (8) | −0.0013 (9) | −0.0100 (8) | −0.0018 (7) |
C26 | 0.0507 (10) | 0.0289 (8) | 0.0239 (8) | 0.0007 (7) | −0.0061 (7) | −0.0016 (6) |
C27 | 0.0573 (11) | 0.0339 (9) | 0.0230 (8) | 0.0017 (8) | 0.0037 (7) | −0.0010 (7) |
C28 | 0.0497 (10) | 0.0287 (8) | 0.0298 (8) | 0.0011 (7) | 0.0092 (8) | −0.0034 (6) |
C29 | 0.0390 (9) | 0.0316 (8) | 0.0300 (8) | 0.0024 (7) | 0.0005 (7) | −0.0053 (6) |
O29 | 0.0370 (7) | 0.0553 (8) | 0.0353 (7) | 0.0001 (6) | 0.0009 (5) | −0.0097 (6) |
C30 | 0.0543 (11) | 0.0391 (10) | 0.0395 (10) | 0.0020 (8) | 0.0136 (8) | −0.0017 (8) |
C31 | 0.0355 (9) | 0.0481 (11) | 0.0532 (12) | 0.0012 (8) | 0.0081 (8) | −0.0028 (9) |
O32 | 0.0366 (6) | 0.0624 (8) | 0.0206 (5) | 0.0095 (6) | −0.0038 (5) | −0.0135 (5) |
C33 | 0.0368 (9) | 0.0404 (9) | 0.0218 (7) | 0.0026 (7) | −0.0013 (6) | −0.0071 (6) |
O34 | 0.0438 (6) | 0.0347 (6) | 0.0173 (5) | −0.0033 (5) | 0.0044 (4) | −0.0036 (4) |
C34 | 0.0306 (8) | 0.0335 (8) | 0.0190 (7) | −0.0012 (6) | −0.0001 (6) | −0.0044 (6) |
C35 | 0.0317 (8) | 0.0313 (7) | 0.0215 (7) | 0.0001 (6) | 0.0000 (6) | −0.0043 (6) |
C36 | 0.0350 (9) | 0.0389 (9) | 0.0326 (9) | 0.0031 (7) | −0.0006 (7) | −0.0047 (7) |
C37 | 0.0441 (10) | 0.0363 (9) | 0.0302 (8) | −0.0033 (7) | 0.0034 (7) | 0.0002 (7) |
S1A—O1A | 1.490 (1) | C13—H132 | 0.9900 |
S1A—C2A | 1.760 (2) | C14—O14 | 1.418 (2) |
S1A—C1A | 1.762 (3) | C14—C15 | 1.540 (2) |
C1A—H11A | 0.9800 | C14—H14 | 1.0000 |
C1A—H12A | 0.9800 | O14—C35 | 1.443 (2) |
C1A—H13A | 0.9800 | C15—O34 | 1.444 (2) |
C2A—H21A | 0.9800 | C15—C17 | 1.515 (2) |
C2A—H22A | 0.9800 | C15—C16 | 1.515 (2) |
C2A—H23A | 0.9800 | C16—H161 | 0.9800 |
S1B—O1B | 1.491 (3) | C16—H162 | 0.9800 |
S1B—C1B | 1.768 (6) | C16—H163 | 0.9800 |
S1B—C2B | 1.772 (4) | C17—H171 | 0.9800 |
C1B—H11B | 0.9800 | C17—H172 | 0.9800 |
C1B—H12B | 0.9800 | C17—H173 | 0.9800 |
C1B—H13B | 0.9800 | C21—O32 | 1.359 (2) |
C2B—H21B | 0.9800 | C21—C22 | 1.385 (2) |
C2B—H22B | 0.9800 | C21—C29 | 1.394 (2) |
C2B—H23B | 0.9800 | C22—O22 | 1.373 (2) |
S1C—O1C | 1.489 (4) | C22—C26 | 1.410 (2) |
S1C—C2C | 1.764 (6) | O22—C23 | 1.364 (2) |
S1C—C1C | 1.765 (6) | C23—O23 | 1.209 (2) |
C1C—H11C | 0.9800 | C23—C24 | 1.435 (3) |
C1C—H12C | 0.9800 | C24—C25 | 1.319 (3) |
C1C—H13C | 0.9800 | C24—H24 | 0.9500 |
C2C—H21C | 0.9800 | C25—C26 | 1.426 (3) |
C2C—H22C | 0.9800 | C25—H25 | 0.9500 |
C2C—H23C | 0.9800 | C26—C27 | 1.388 (3) |
C1—O12 | 1.364 (2) | C27—C28 | 1.375 (3) |
C1—C9 | 1.382 (2) | C27—H27 | 0.9500 |
C1—C2 | 1.386 (2) | C28—C29 | 1.401 (2) |
C2—O2 | 1.369 (2) | C28—C30 | 1.453 (3) |
C2—C6 | 1.407 (2) | C29—O29 | 1.366 (2) |
O2—C3 | 1.374 (2) | O29—C31 | 1.378 (2) |
C3—O3 | 1.202 (2) | C30—C31 | 1.341 (3) |
C3—C4 | 1.441 (3) | C30—H30 | 0.9500 |
C4—C5 | 1.324 (3) | C31—H31 | 0.9500 |
C4—H4 | 0.9500 | O32—C33 | 1.439 (2) |
C5—C6 | 1.442 (3) | C33—C34 | 1.512 (2) |
C5—H5 | 0.9500 | C33—H331 | 0.9900 |
C6—C7 | 1.388 (3) | C33—H332 | 0.9900 |
C7—C8 | 1.379 (3) | O34—C34 | 1.415 (2) |
C7—H7 | 0.9500 | C34—C35 | 1.549 (2) |
C8—C9 | 1.403 (2) | C34—H34 | 1.0000 |
C8—C10 | 1.438 (3) | C35—C36 | 1.516 (2) |
C9—O9 | 1.364 (2) | C35—C37 | 1.520 (2) |
O9—C11 | 1.380 (2) | C36—H361 | 0.9800 |
C10—C11 | 1.335 (3) | C36—H362 | 0.9800 |
C10—H10 | 0.9500 | C36—H363 | 0.9800 |
C11—H11 | 0.9500 | C37—H371 | 0.9800 |
O12—C13 | 1.437 (2) | C37—H372 | 0.9800 |
C13—C14 | 1.505 (2) | C37—H373 | 0.9800 |
C13—H131 | 0.9900 | ||
O1A—S1A—C2A | 106.5 (1) | C17—C15—C16 | 111.8 (2) |
O1A—S1A—C1A | 106.8 (1) | O34—C15—C14 | 108.2 (1) |
C2A—S1A—C1A | 98.6 (2) | C17—C15—C14 | 110.2 (1) |
S1A—C1A—H11A | 109.5 | C16—C15—C14 | 112.4 (1) |
S1A—C1A—H12A | 109.5 | C15—C16—H161 | 109.5 |
H11A—C1A—H12A | 109.5 | C15—C16—H162 | 109.5 |
S1A—C1A—H13A | 109.5 | H161—C16—H162 | 109.5 |
H11A—C1A—H13A | 109.5 | C15—C16—H163 | 109.5 |
H12A—C1A—H13A | 109.5 | H161—C16—H163 | 109.5 |
S1A—C2A—H21A | 109.5 | H162—C16—H163 | 109.5 |
S1A—C2A—H22A | 109.5 | C15—C17—H171 | 109.5 |
H21A—C2A—H22A | 109.5 | C15—C17—H172 | 109.5 |
S1A—C2A—H23A | 109.5 | H171—C17—H172 | 109.5 |
H21A—C2A—H23A | 109.5 | C15—C17—H173 | 109.5 |
H22A—C2A—H23A | 109.5 | H171—C17—H173 | 109.5 |
O1B—S1B—C1B | 106.0 (3) | H172—C17—H173 | 109.5 |
O1B—S1B—C2B | 106.4 (2) | O32—C21—C22 | 117.9 (2) |
C1B—S1B—C2B | 95.6 (3) | O32—C21—C29 | 127.4 (2) |
O1C—S1C—C2C | 106.5 (3) | C22—C21—C29 | 114.5 (1) |
O1C—S1C—C1C | 106.9 (4) | O22—C22—C21 | 116.0 (1) |
C2C—S1C—C1C | 97.7 (4) | O22—C22—C26 | 120.6 (2) |
S1C—C1C—H11C | 109.5 | C21—C22—C26 | 123.3 (2) |
S1C—C1C—H12C | 109.5 | C23—O22—C22 | 121.8 (1) |
H11C—C1C—H12C | 109.5 | O23—C23—O22 | 115.5 (2) |
S1C—C1C—H13C | 109.5 | O23—C23—C24 | 126.9 (2) |
H11C—C1C—H13C | 109.5 | O22—C23—C24 | 117.6 (2) |
H12C—C1C—H13C | 109.5 | C25—C24—C23 | 121.3 (2) |
S1C—C2C—H21C | 109.5 | C25—C24—H24 | 119.3 |
S1C—C2C—H22C | 109.5 | C23—C24—H24 | 119.3 |
H21C—C2C—H22C | 109.5 | C24—C25—C26 | 121.5 (2) |
S1C—C2C—H23C | 109.5 | C24—C25—H25 | 119.2 |
H21C—C2C—H23C | 109.5 | C26—C25—H25 | 119.2 |
H22C—C2C—H23C | 109.5 | C27—C26—C22 | 119.7 (2) |
O12—C1—C9 | 125.8 (1) | C27—C26—C25 | 123.4 (2) |
O12—C1—C2 | 118.4 (1) | C22—C26—C25 | 116.9 (2) |
C9—C1—C2 | 115.2 (1) | C28—C27—C26 | 118.8 (2) |
O2—C2—C1 | 116.1 (1) | C28—C27—H27 | 120.6 |
O2—C2—C6 | 121.3 (1) | C26—C27—H27 | 120.6 |
C1—C2—C6 | 122.6 (2) | C27—C28—C29 | 119.8 (2) |
C2—O2—C3 | 122.0 (1) | C27—C28—C30 | 135.0 (2) |
O3—C3—O2 | 116.6 (2) | C29—C28—C30 | 105.2 (2) |
O3—C3—C4 | 126.3 (2) | O29—C29—C21 | 126.0 (1) |
O2—C3—C4 | 117.2 (2) | O29—C29—C28 | 110.3 (2) |
C5—C4—C3 | 121.7 (2) | C21—C29—C28 | 123.7 (2) |
C5—C4—H4 | 119.1 | C29—O29—C31 | 106.1 (1) |
C3—C4—H4 | 119.1 | C31—C30—C28 | 106.0 (2) |
C4—C5—C6 | 121.2 (2) | C31—C30—H30 | 127.0 |
C4—C5—H5 | 119.4 | C28—C30—H30 | 127.0 |
C6—C5—H5 | 119.4 | C30—C31—O29 | 112.4 (2) |
C7—C6—C2 | 120.3 (2) | C30—C31—H31 | 123.8 |
C7—C6—C5 | 123.0 (2) | O29—C31—H31 | 123.8 |
C2—C6—C5 | 116.6 (2) | C21—O32—C33 | 119.2 (1) |
C8—C7—C6 | 118.4 (1) | O32—C33—C34 | 106.6 (1) |
C8—C7—H7 | 120.8 | O32—C33—H331 | 110.4 |
C6—C7—H7 | 120.8 | C34—C33—H331 | 110.4 |
C7—C8—C9 | 119.7 (2) | O32—C33—H332 | 110.4 |
C7—C8—C10 | 135.3 (2) | C34—C33—H332 | 110.4 |
C9—C8—C10 | 104.9 (2) | H331—C33—H332 | 108.6 |
O9—C9—C1 | 125.8 (1) | C34—O34—C15 | 114.3 (1) |
O9—C9—C8 | 110.4 (2) | O34—C34—C33 | 107.1 (1) |
C1—C9—C8 | 123.8 (2) | O34—C34—C35 | 109.7 (1) |
C9—O9—C11 | 105.8 (1) | C33—C34—C35 | 112.6 (1) |
C11—C10—C8 | 106.9 (2) | O34—C34—H34 | 109.1 |
C11—C10—H10 | 126.6 | C33—C34—H34 | 109.1 |
C8—C10—H10 | 126.6 | C35—C34—H34 | 109.1 |
C10—C11—O9 | 112.0 (2) | O14—C35—C36 | 104.5 (1) |
C10—C11—H11 | 124.0 | O14—C35—C37 | 108.6 (1) |
O9—C11—H11 | 124.0 | C36—C35—C37 | 111.8 (1) |
C1—O12—C13 | 117.1 (1) | O14—C35—C34 | 108.6 (1) |
O12—C13—C14 | 106.8 (1) | C36—C35—C34 | 112.5 (1) |
O12—C13—H131 | 110.4 | C37—C35—C34 | 110.6 (1) |
C14—C13—H131 | 110.4 | C35—C36—H361 | 109.5 |
O12—C13—H132 | 110.4 | C35—C36—H362 | 109.5 |
C14—C13—H132 | 110.4 | H361—C36—H362 | 109.5 |
H131—C13—H132 | 108.6 | C35—C36—H363 | 109.5 |
O14—C14—C13 | 107.6 (1) | H361—C36—H363 | 109.5 |
O14—C14—C15 | 109.9 (1) | H362—C36—H363 | 109.5 |
C13—C14—C15 | 113.0 (1) | C35—C37—H371 | 109.5 |
O14—C14—H14 | 108.7 | C35—C37—H372 | 109.5 |
C13—C14—H14 | 108.7 | H371—C37—H372 | 109.5 |
C15—C14—H14 | 108.7 | C35—C37—H373 | 109.5 |
C14—O14—C35 | 113.5 (1) | H371—C37—H373 | 109.5 |
O34—C15—C17 | 109.6 (1) | H372—C37—H373 | 109.5 |
O34—C15—C16 | 104.4 (1) | ||
O12—C1—C2—O2 | 6.4 (2) | C29—C21—C22—C26 | 2.7 (2) |
C9—C1—C2—O2 | 178.6 (1) | C21—C22—O22—C23 | 176.0 (2) |
O12—C1—C2—C6 | −171.9 (2) | C26—C22—O22—C23 | −3.6 (2) |
C9—C1—C2—C6 | 0.3 (2) | C22—O22—C23—O23 | −174.5 (2) |
C1—C2—O2—C3 | −176.5 (1) | C22—O22—C23—C24 | 5.8 (2) |
C6—C2—O2—C3 | 1.8 (2) | O23—C23—C24—C25 | 176.0 (2) |
C2—O2—C3—O3 | 179.1 (2) | O22—C23—C24—C25 | −4.3 (3) |
C2—O2—C3—C4 | −1.3 (2) | C23—C24—C25—C26 | 0.6 (3) |
O3—C3—C4—C5 | 179.5 (2) | O22—C22—C26—C27 | 178.3 (2) |
O2—C3—C4—C5 | 0.0 (3) | C21—C22—C26—C27 | −1.2 (3) |
C3—C4—C5—C6 | 0.8 (3) | O22—C22—C26—C25 | −0.3 (2) |
O2—C2—C6—C7 | −178.5 (2) | C21—C22—C26—C25 | −179.8 (2) |
C1—C2—C6—C7 | −0.3 (3) | C24—C25—C26—C27 | −176.9 (2) |
O2—C2—C6—C5 | −1.0 (3) | C24—C25—C26—C22 | 1.7 (3) |
C1—C2—C6—C5 | 177.3 (2) | C22—C26—C27—C28 | −1.3 (3) |
C4—C5—C6—C7 | 177.1 (2) | C25—C26—C27—C28 | 177.2 (2) |
C4—C5—C6—C2 | −0.3 (3) | C26—C27—C28—C29 | 2.0 (2) |
C2—C6—C7—C8 | 0.3 (3) | C26—C27—C28—C30 | −176.9 (2) |
C5—C6—C7—C8 | −177.1 (2) | O32—C21—C29—O29 | −7.3 (3) |
C6—C7—C8—C9 | −0.3 (3) | C22—C21—C29—O29 | 177.0 (2) |
C6—C7—C8—C10 | 175.6 (2) | O32—C21—C29—C28 | 173.6 (2) |
O12—C1—C9—O9 | −5.5 (3) | C22—C21—C29—C28 | −2.0 (2) |
C2—C1—C9—O9 | −177.0 (2) | C27—C28—C29—O29 | −179.5 (2) |
O12—C1—C9—C8 | 171.2 (2) | C30—C28—C29—O29 | −0.3 (2) |
C2—C1—C9—C8 | −0.4 (2) | C27—C28—C29—C21 | −0.3 (3) |
C7—C8—C9—O9 | 177.5 (2) | C30—C28—C29—C21 | 178.9 (2) |
C10—C8—C9—O9 | 0.5 (2) | C21—C29—O29—C31 | −178.7 (2) |
C7—C8—C9—C1 | 0.4 (3) | C28—C29—O29—C31 | 0.5 (2) |
C10—C8—C9—C1 | −176.7 (2) | C27—C28—C30—C31 | 178.9 (2) |
C1—C9—O9—C11 | 176.2 (2) | C29—C28—C30—C31 | 0.0 (2) |
C8—C9—O9—C11 | −0.9 (2) | C28—C30—C31—O29 | 0.4 (2) |
C7—C8—C10—C11 | −176.2 (2) | C29—O29—C31—C30 | −0.6 (2) |
C9—C8—C10—C11 | 0.1 (2) | C22—C21—O32—C33 | −146.1 (2) |
C8—C10—C11—O9 | −0.7 (2) | C29—C21—O32—C33 | 38.4 (3) |
C9—O9—C11—C10 | 1.0 (2) | C21—O32—C33—C34 | −164.1 (2) |
C9—C1—O12—C13 | 51.1 (2) | C17—C15—O34—C34 | 93.7 (2) |
C2—C1—O12—C13 | −137.6 (2) | C16—C15—O34—C34 | −146.5 (1) |
C1—O12—C13—C14 | −170.7 (1) | C14—C15—O34—C34 | −26.5 (2) |
O12—C13—C14—O14 | 79.4 (2) | C15—O34—C34—C33 | −171.4 (1) |
O12—C13—C14—C15 | −159.1 (1) | C15—O34—C34—C35 | 66.1 (2) |
C13—C14—O14—C35 | −169.0 (1) | O32—C33—C34—O34 | 75.0 (2) |
C15—C14—O14—C35 | 67.6 (2) | O32—C33—C34—C35 | −164.3 (1) |
O14—C14—C15—O34 | −38.0 (2) | C14—O14—C35—C36 | −147.9 (1) |
C13—C14—C15—O34 | −158.2 (1) | C14—O14—C35—C37 | 92.8 (2) |
O14—C14—C15—C17 | −157.8 (1) | C14—O14—C35—C34 | −27.6 (2) |
C13—C14—C15—C17 | 82.0 (2) | O34—C34—C35—O14 | −36.4 (2) |
O14—C14—C15—C16 | 76.8 (2) | C33—C34—C35—O14 | −155.5 (1) |
C13—C14—C15—C16 | −43.4 (2) | O34—C34—C35—C36 | 78.8 (2) |
O32—C21—C22—O22 | 7.1 (2) | C33—C34—C35—C36 | −40.4 (2) |
C29—C21—C22—O22 | −176.8 (1) | O34—C34—C35—C37 | −155.4 (1) |
O32—C21—C22—C26 | −173.4 (2) | C33—C34—C35—C37 | 85.5 (2) |
C32H28O10·C3H7NO | F(000) = 680 |
Mr = 645.64 | Dx = 1.393 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 7355 reflections |
a = 8.2000 (7) Å | θ = 2.2–28.1° |
b = 16.2132 (14) Å | µ = 0.10 mm−1 |
c = 11.6706 (10) Å | T = 200 K |
β = 97.244 (1)° | Plate, colourless |
V = 1539.2 (2) Å3 | 0.50 × 0.40 × 0.04 mm |
Z = 2 |
Bruker SMART APEX area-detector diffractometer | 3516 independent reflections |
Radiation source: MacScience, M18XCE rotating anode | 3381 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.1°, θmin = 2.2° |
ω scan | h = −10→10 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −20→20 |
Tmin = 0.932, Tmax = 1.0 | l = −14→14 |
13520 measured reflections |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0757P)2 + 0.3442P] where P = (Fo2 + 2Fc2)/3 |
3516 reflections | (Δ/σ)max < 0.001 |
430 parameters | Δρmax = 0.67 e Å−3 |
3 restraints | Δρmin = −0.38 e Å−3 |
C32H28O10·C3H7NO | V = 1539.2 (2) Å3 |
Mr = 645.64 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.2000 (7) Å | µ = 0.10 mm−1 |
b = 16.2132 (14) Å | T = 200 K |
c = 11.6706 (10) Å | 0.50 × 0.40 × 0.04 mm |
β = 97.244 (1)° |
Bruker SMART APEX area-detector diffractometer | 3516 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 3381 reflections with I > 2σ(I) |
Tmin = 0.932, Tmax = 1.0 | Rint = 0.017 |
13520 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 3 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.67 e Å−3 |
3516 reflections | Δρmin = −0.38 e Å−3 |
430 parameters |
Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) − 1.6136 (0.0048) x + 4.9254 (0.0096) y − 10.5029 (0.0041) z = 7.4050 (0.0059) * −0.0559 (0.0022) C21 * −0.0162 (0.0025) C22 * 0.0332 (0.0021) O22 * 0.0584 (0.0027) C23 * 0.0121 (0.0028) C24 * −0.0214 (0.0026) C25 * −0.0133 (0.0026) C26 * −0.0310 (0.0026) C27 * −0.0246 (0.0026) C28 * −0.0534 (0.0025) C29 * 0.0550 (0.0027) C30 * 0.0633 (0.0027) C31 * −0.0063 (0.0020) O29 Rms deviation of fitted atoms = 0.0394 − 1.2969 (0.0049) x − 0.8595 (0.0107) y + 11.6480 (0.0011) z = 2.8726 (0.0072) Angle to previous plane (with approximate e.s.d.) = 25.30 (0.04) * −0.0456 (0.0024) C1 * −0.0521 (0.0025) C2 * −0.0044 (0.0021) O2 * 0.0685 (0.0027) C3 * 0.0512 (0.0030) C4 * −0.0184 (0.0028) C5 * −0.0470 (0.0027) C6 * −0.0274 (0.0028) C7 * −0.0050 (0.0029) C8 * −0.0182 (0.0026) C9 * 0.0323 (0.0031) C10 * 0.0454 (0.0032) C11 * 0.0207 (0.0022) O9 Rms deviation of fitted atoms = 0.0385 |
Refinement. In the absence of significant anomalous scattering effects, Friedel pairs were merged, and the absolute configuration is assumed from that of the crystal structure obtained from dimethylsulfoxide solution. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2453 (4) | 0.77989 (18) | 0.3276 (2) | 0.0327 (6) | |
C2 | 0.4125 (4) | 0.79808 (19) | 0.3469 (2) | 0.0349 (6) | |
O2 | 0.4540 (2) | 0.87951 (15) | 0.36168 (18) | 0.0389 (5) | |
C3 | 0.6158 (4) | 0.9053 (3) | 0.3879 (3) | 0.0495 (9) | |
O3 | 0.6368 (4) | 0.9778 (2) | 0.4010 (3) | 0.0691 (9) | |
C4 | 0.7386 (4) | 0.8414 (4) | 0.3953 (3) | 0.0631 (12) | |
H4 | 0.8510 | 0.8564 | 0.4124 | 0.076* | |
C5 | 0.7015 (5) | 0.7631 (3) | 0.3794 (3) | 0.0577 (11) | |
H5 | 0.7877 | 0.7237 | 0.3834 | 0.069* | |
C6 | 0.5334 (4) | 0.7354 (2) | 0.3562 (2) | 0.0460 (8) | |
C7 | 0.4877 (5) | 0.6528 (2) | 0.3467 (3) | 0.0555 (10) | |
H7 | 0.5688 | 0.6107 | 0.3525 | 0.067* | |
C8 | 0.3219 (5) | 0.6329 (2) | 0.3287 (3) | 0.0509 (9) | |
C9 | 0.2051 (4) | 0.69606 (19) | 0.3192 (2) | 0.0396 (7) | |
O9 | 0.0498 (3) | 0.66622 (15) | 0.3031 (2) | 0.0492 (6) | |
C10 | 0.2238 (8) | 0.5581 (3) | 0.3155 (3) | 0.0698 (14) | |
H10 | 0.2642 | 0.5032 | 0.3170 | 0.084* | |
C11 | 0.0670 (7) | 0.5810 (2) | 0.3008 (3) | 0.0636 (12) | |
H11 | −0.0228 | 0.5436 | 0.2901 | 0.076* | |
O12 | 0.1233 (2) | 0.83701 (13) | 0.33009 (17) | 0.0335 (4) | |
C13 | 0.1077 (3) | 0.89826 (16) | 0.2396 (2) | 0.0315 (5) | |
H131 | 0.2182 | 0.9202 | 0.2310 | 0.038* | |
H132 | 0.0402 | 0.9446 | 0.2627 | 0.038* | |
C14 | 0.0306 (3) | 0.86529 (15) | 0.1246 (2) | 0.0267 (5) | |
H14 | 0.0907 | 0.8148 | 0.1043 | 0.032* | |
O14 | −0.1350 (2) | 0.84472 (12) | 0.13681 (16) | 0.0305 (4) | |
C15 | 0.0321 (3) | 0.93058 (16) | 0.0279 (2) | 0.0302 (5) | |
C16 | 0.1916 (4) | 0.9253 (2) | −0.0256 (3) | 0.0422 (7) | |
H161 | 0.1880 | 0.9645 | −0.0899 | 0.063* | |
H162 | 0.2053 | 0.8693 | −0.0542 | 0.063* | |
H163 | 0.2843 | 0.9389 | 0.0329 | 0.063* | |
C17 | 0.0007 (4) | 1.01791 (18) | 0.0679 (3) | 0.0425 (7) | |
H171 | −0.0944 | 1.0179 | 0.1110 | 0.064* | |
H172 | −0.0215 | 1.0542 | 0.0005 | 0.064* | |
H173 | 0.0977 | 1.0379 | 0.1178 | 0.064* | |
C21 | −0.0944 (3) | 0.78052 (18) | −0.3192 (2) | 0.0318 (5) | |
C22 | 0.0645 (3) | 0.80042 (19) | −0.3381 (2) | 0.0342 (6) | |
O22 | 0.1137 (3) | 0.87989 (15) | −0.3130 (2) | 0.0419 (5) | |
C23 | 0.2697 (4) | 0.9076 (3) | −0.3264 (3) | 0.0510 (9) | |
O23 | 0.2993 (4) | 0.9785 (2) | −0.3024 (3) | 0.0695 (8) | |
C24 | 0.3799 (4) | 0.8473 (3) | −0.3672 (3) | 0.0581 (11) | |
H24 | 0.4891 | 0.8635 | −0.3758 | 0.070* | |
C25 | 0.3336 (4) | 0.7710 (3) | −0.3927 (3) | 0.0522 (10) | |
H25 | 0.4100 | 0.7336 | −0.4191 | 0.063* | |
C26 | 0.1701 (4) | 0.7430 (2) | −0.3815 (2) | 0.0418 (7) | |
C27 | 0.1158 (4) | 0.6634 (2) | −0.4088 (3) | 0.0476 (8) | |
H27 | 0.1871 | 0.6241 | −0.4366 | 0.057* | |
C28 | −0.0433 (5) | 0.6424 (2) | −0.3948 (3) | 0.0432 (7) | |
C29 | −0.1445 (4) | 0.70026 (19) | −0.3494 (2) | 0.0353 (6) | |
O29 | −0.2978 (3) | 0.66946 (14) | −0.34475 (18) | 0.0413 (5) | |
C30 | −0.1474 (6) | 0.5715 (2) | −0.4196 (3) | 0.0533 (9) | |
H30 | −0.1169 | 0.5208 | −0.4518 | 0.064* | |
C31 | −0.2955 (5) | 0.5901 (2) | −0.3890 (3) | 0.0499 (8) | |
H31 | −0.3869 | 0.5536 | −0.3965 | 0.060* | |
O32 | −0.1958 (2) | 0.83920 (13) | −0.28315 (16) | 0.0338 (4) | |
C33 | −0.2680 (3) | 0.82090 (18) | −0.1791 (2) | 0.0321 (5) | |
H331 | −0.3110 | 0.7638 | −0.1837 | 0.038* | |
H332 | −0.3617 | 0.8586 | −0.1740 | 0.038* | |
C34 | −0.1458 (3) | 0.82979 (16) | −0.0711 (2) | 0.0272 (5) | |
H34 | −0.0446 | 0.7972 | −0.0801 | 0.033* | |
O34 | −0.1050 (2) | 0.91437 (11) | −0.05982 (17) | 0.0312 (4) | |
C35 | −0.2179 (3) | 0.80034 (16) | 0.0393 (2) | 0.0290 (5) | |
C36 | −0.1919 (4) | 0.70822 (19) | 0.0567 (3) | 0.0411 (7) | |
H361 | −0.2311 | 0.6914 | 0.1291 | 0.062* | |
H362 | −0.0745 | 0.6955 | 0.0602 | 0.062* | |
H363 | −0.2532 | 0.6783 | −0.0079 | 0.062* | |
C37 | −0.3979 (3) | 0.8233 (2) | 0.0392 (3) | 0.0389 (6) | |
H371 | −0.4121 | 0.8825 | 0.0242 | 0.058* | |
H372 | −0.4322 | 0.8101 | 0.1145 | 0.058* | |
H373 | −0.4653 | 0.7921 | −0.0213 | 0.058* | |
N1D | −0.6127 (3) | 0.61071 (17) | −0.0546 (3) | 0.0440 (6) | |
C2D | −0.5685 (5) | 0.5730 (3) | 0.0546 (3) | 0.0584 (9) | |
H21D | −0.6438 | 0.5272 | 0.0640 | 0.088* | |
H22D | −0.5753 | 0.6137 | 0.1159 | 0.088* | |
H23D | −0.4558 | 0.5519 | 0.0594 | 0.088* | |
C3D | −0.5601 (7) | 0.5724 (4) | −0.1535 (4) | 0.0828 (15) | |
H31D | −0.6119 | 0.6000 | −0.2235 | 0.124* | |
H32D | −0.5920 | 0.5141 | −0.1556 | 0.124* | |
H33D | −0.4403 | 0.5768 | −0.1495 | 0.124* | |
C4D | −0.7181 (5) | 0.6721 (3) | −0.0736 (6) | 0.0862 (18) | |
H4D | −0.7445 | 0.6859 | −0.1529 | 0.103* | |
O4D | −0.7842 (5) | 0.7121 (3) | −0.0125 (6) | 0.133 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0371 (14) | 0.0372 (14) | 0.0236 (12) | 0.0088 (11) | 0.0034 (10) | 0.0023 (10) |
C2 | 0.0354 (13) | 0.0443 (16) | 0.0254 (12) | 0.0132 (12) | 0.0051 (10) | 0.0045 (11) |
O2 | 0.0287 (9) | 0.0523 (13) | 0.0349 (10) | 0.0046 (9) | 0.0009 (8) | 0.0074 (9) |
C3 | 0.0324 (15) | 0.079 (3) | 0.0362 (15) | −0.0046 (16) | 0.0010 (12) | 0.0173 (16) |
O3 | 0.0482 (15) | 0.078 (2) | 0.0766 (19) | −0.0194 (14) | −0.0091 (13) | 0.0220 (17) |
C4 | 0.0280 (14) | 0.114 (4) | 0.0474 (19) | 0.011 (2) | 0.0055 (13) | 0.026 (2) |
C5 | 0.0402 (17) | 0.099 (3) | 0.0350 (16) | 0.035 (2) | 0.0108 (13) | 0.0166 (18) |
C6 | 0.0443 (16) | 0.069 (2) | 0.0263 (13) | 0.0318 (16) | 0.0090 (11) | 0.0073 (13) |
C7 | 0.078 (3) | 0.059 (2) | 0.0299 (14) | 0.045 (2) | 0.0083 (15) | 0.0049 (14) |
C8 | 0.085 (3) | 0.0391 (17) | 0.0282 (14) | 0.0214 (17) | 0.0050 (15) | 0.0006 (12) |
C9 | 0.0543 (17) | 0.0383 (15) | 0.0259 (13) | 0.0046 (13) | 0.0041 (12) | 0.0007 (11) |
O9 | 0.0656 (15) | 0.0415 (12) | 0.0386 (11) | −0.0059 (11) | −0.0003 (10) | 0.0008 (10) |
C10 | 0.134 (5) | 0.0350 (17) | 0.0402 (19) | 0.015 (2) | 0.011 (2) | 0.0002 (14) |
C11 | 0.108 (4) | 0.0385 (19) | 0.0425 (19) | −0.012 (2) | 0.005 (2) | 0.0029 (15) |
O12 | 0.0292 (9) | 0.0375 (10) | 0.0333 (9) | 0.0067 (8) | 0.0020 (7) | 0.0034 (8) |
C13 | 0.0297 (12) | 0.0243 (11) | 0.0385 (14) | 0.0035 (10) | −0.0034 (10) | −0.0002 (10) |
C14 | 0.0227 (10) | 0.0222 (11) | 0.0345 (13) | 0.0026 (8) | 0.0013 (9) | −0.0001 (9) |
O14 | 0.0258 (8) | 0.0327 (10) | 0.0327 (9) | −0.0036 (7) | 0.0027 (7) | −0.0041 (8) |
C15 | 0.0249 (11) | 0.0254 (12) | 0.0385 (14) | −0.0020 (9) | −0.0032 (10) | 0.0026 (10) |
C16 | 0.0278 (13) | 0.0506 (18) | 0.0473 (16) | −0.0063 (12) | 0.0016 (12) | 0.0065 (14) |
C17 | 0.0453 (16) | 0.0232 (12) | 0.0554 (18) | 0.0015 (11) | −0.0081 (14) | 0.0012 (12) |
C21 | 0.0336 (13) | 0.0367 (14) | 0.0247 (12) | 0.0059 (11) | 0.0023 (10) | 0.0025 (10) |
C22 | 0.0327 (13) | 0.0433 (15) | 0.0264 (12) | 0.0060 (11) | 0.0031 (10) | 0.0047 (11) |
O22 | 0.0341 (10) | 0.0499 (13) | 0.0425 (11) | −0.0051 (9) | 0.0079 (8) | 0.0026 (10) |
C23 | 0.0403 (16) | 0.075 (3) | 0.0379 (16) | −0.0147 (16) | 0.0059 (13) | 0.0115 (16) |
O23 | 0.0622 (17) | 0.077 (2) | 0.0711 (18) | −0.0298 (16) | 0.0146 (14) | 0.0066 (16) |
C24 | 0.0305 (14) | 0.112 (4) | 0.0320 (15) | 0.0002 (18) | 0.0057 (12) | 0.0136 (18) |
C25 | 0.0360 (16) | 0.092 (3) | 0.0292 (14) | 0.0179 (18) | 0.0067 (12) | 0.0096 (16) |
C26 | 0.0367 (14) | 0.065 (2) | 0.0243 (12) | 0.0163 (14) | 0.0058 (10) | 0.0075 (13) |
C27 | 0.0554 (19) | 0.060 (2) | 0.0283 (14) | 0.0278 (16) | 0.0079 (12) | 0.0033 (13) |
C28 | 0.0623 (19) | 0.0410 (16) | 0.0258 (13) | 0.0161 (14) | 0.0031 (12) | 0.0040 (11) |
C29 | 0.0420 (15) | 0.0372 (14) | 0.0259 (12) | 0.0055 (12) | 0.0011 (11) | 0.0042 (11) |
O29 | 0.0486 (12) | 0.0383 (11) | 0.0367 (11) | −0.0042 (9) | 0.0036 (9) | 0.0000 (9) |
C30 | 0.088 (3) | 0.0370 (16) | 0.0334 (15) | 0.0096 (17) | 0.0019 (16) | 0.0022 (12) |
C31 | 0.074 (2) | 0.0352 (15) | 0.0385 (16) | −0.0046 (16) | −0.0007 (15) | 0.0036 (13) |
O32 | 0.0320 (9) | 0.0362 (10) | 0.0334 (10) | 0.0044 (8) | 0.0050 (7) | 0.0019 (8) |
C33 | 0.0253 (11) | 0.0395 (14) | 0.0312 (12) | −0.0010 (10) | 0.0030 (9) | −0.0020 (11) |
C34 | 0.0216 (10) | 0.0274 (12) | 0.0323 (12) | 0.0018 (9) | 0.0021 (9) | −0.0020 (10) |
O34 | 0.0262 (9) | 0.0290 (10) | 0.0366 (10) | −0.0001 (7) | −0.0035 (7) | 0.0043 (7) |
C35 | 0.0246 (11) | 0.0289 (12) | 0.0333 (12) | −0.0028 (9) | 0.0028 (9) | −0.0024 (10) |
C36 | 0.0467 (16) | 0.0296 (14) | 0.0458 (16) | −0.0062 (12) | 0.0019 (13) | 0.0000 (12) |
C37 | 0.0243 (11) | 0.0529 (17) | 0.0402 (14) | −0.0045 (12) | 0.0074 (10) | −0.0043 (13) |
N1D | 0.0378 (13) | 0.0369 (13) | 0.0572 (16) | 0.0002 (11) | 0.0058 (11) | 0.0051 (12) |
C2D | 0.063 (2) | 0.070 (3) | 0.0417 (18) | −0.0123 (19) | 0.0071 (16) | −0.0037 (17) |
C3D | 0.091 (3) | 0.120 (5) | 0.039 (2) | 0.000 (3) | 0.013 (2) | 0.007 (2) |
C4D | 0.045 (2) | 0.043 (2) | 0.169 (6) | −0.0021 (18) | 0.010 (3) | 0.009 (3) |
O4D | 0.058 (2) | 0.064 (2) | 0.277 (7) | 0.0061 (17) | 0.024 (3) | −0.060 (3) |
C1—O12 | 1.366 (3) | O22—C23 | 1.383 (4) |
C1—C2 | 1.392 (4) | C23—O23 | 1.200 (5) |
C1—C9 | 1.399 (4) | C23—C24 | 1.452 (6) |
C2—O2 | 1.369 (4) | C24—C25 | 1.318 (7) |
C2—C6 | 1.415 (4) | C24—H24 | 0.9500 |
O2—C3 | 1.388 (4) | C25—C26 | 1.437 (5) |
C3—O3 | 1.195 (5) | C25—H25 | 0.9500 |
C3—C4 | 1.440 (6) | C26—C27 | 1.390 (6) |
C4—C5 | 1.312 (8) | C27—C28 | 1.377 (5) |
C4—H4 | 0.9500 | C27—H27 | 0.9500 |
C5—C6 | 1.443 (6) | C28—C29 | 1.400 (4) |
C5—H5 | 0.9500 | C28—C30 | 1.440 (5) |
C6—C7 | 1.391 (6) | C29—O29 | 1.360 (4) |
C7—C8 | 1.387 (6) | O29—C31 | 1.387 (4) |
C7—H7 | 0.9500 | C30—C31 | 1.343 (6) |
C8—C9 | 1.397 (5) | C30—H30 | 0.9500 |
C8—C10 | 1.452 (7) | C31—H31 | 0.9500 |
C9—O9 | 1.353 (4) | O32—C33 | 1.447 (3) |
O9—C11 | 1.389 (5) | C33—C34 | 1.516 (3) |
C10—C11 | 1.329 (8) | C33—H331 | 0.9900 |
C10—H10 | 0.9500 | C33—H332 | 0.9900 |
C11—H11 | 0.9500 | C34—O34 | 1.414 (3) |
O12—C13 | 1.443 (3) | C34—C35 | 1.559 (4) |
C13—C14 | 1.508 (4) | C34—H34 | 1.0000 |
C13—H131 | 0.9900 | C35—C36 | 1.519 (4) |
C13—H132 | 0.9900 | C35—C37 | 1.522 (3) |
C14—O14 | 1.422 (3) | C36—H361 | 0.9800 |
C14—C15 | 1.548 (4) | C36—H362 | 0.9800 |
C14—H14 | 1.0000 | C36—H363 | 0.9800 |
O14—C35 | 1.442 (3) | C37—H371 | 0.9800 |
C15—O34 | 1.445 (3) | C37—H372 | 0.9800 |
C15—C16 | 1.521 (4) | C37—H373 | 0.9800 |
C15—C17 | 1.523 (4) | N1D—C4D | 1.319 (5) |
C16—H161 | 0.9800 | N1D—C2D | 1.419 (5) |
C16—H162 | 0.9800 | N1D—C3D | 1.424 (6) |
C16—H163 | 0.9800 | C2D—H21D | 0.9800 |
C17—H171 | 0.9800 | C2D—H22D | 0.9800 |
C17—H172 | 0.9800 | C2D—H23D | 0.9800 |
C17—H173 | 0.9800 | C3D—H31D | 0.9800 |
C21—O32 | 1.364 (3) | C3D—H32D | 0.9800 |
C21—C22 | 1.387 (4) | C3D—H33D | 0.9800 |
C21—C29 | 1.396 (4) | C4D—O4D | 1.149 (5) |
C22—O22 | 1.371 (4) | C4D—H4D | 0.9500 |
C22—C26 | 1.408 (4) | ||
O12—C1—C2 | 124.2 (3) | O22—C23—C24 | 116.2 (4) |
O12—C1—C9 | 119.5 (3) | C25—C24—C23 | 122.2 (3) |
C2—C1—C9 | 115.8 (3) | C25—C24—H24 | 118.9 |
O2—C2—C1 | 116.7 (2) | C23—C24—H24 | 118.9 |
O2—C2—C6 | 121.5 (3) | C24—C25—C26 | 121.4 (3) |
C1—C2—C6 | 121.8 (3) | C24—C25—H25 | 119.3 |
C2—O2—C3 | 122.3 (3) | C26—C25—H25 | 119.3 |
O3—C3—O2 | 116.3 (3) | C27—C26—C22 | 120.2 (3) |
O3—C3—C4 | 127.7 (4) | C27—C26—C25 | 123.2 (3) |
O2—C3—C4 | 116.0 (4) | C22—C26—C25 | 116.6 (3) |
C5—C4—C3 | 122.7 (3) | C28—C27—C26 | 118.9 (3) |
C5—C4—H4 | 118.7 | C28—C27—H27 | 120.5 |
C3—C4—H4 | 118.7 | C26—C27—H27 | 120.5 |
C4—C5—C6 | 121.8 (3) | C27—C28—C29 | 119.6 (3) |
C4—C5—H5 | 119.1 | C27—C28—C30 | 136.0 (3) |
C6—C5—H5 | 119.1 | C29—C28—C30 | 104.3 (3) |
C7—C6—C2 | 120.4 (3) | O29—C29—C21 | 125.2 (3) |
C7—C6—C5 | 123.8 (3) | O29—C29—C28 | 111.3 (3) |
C2—C6—C5 | 115.7 (4) | C21—C29—C28 | 123.4 (3) |
C8—C7—C6 | 119.0 (3) | C29—O29—C31 | 105.6 (3) |
C8—C7—H7 | 120.5 | C31—C30—C28 | 107.4 (3) |
C6—C7—H7 | 120.5 | C31—C30—H30 | 126.3 |
C7—C8—C9 | 119.4 (3) | C28—C30—H30 | 126.3 |
C7—C8—C10 | 136.8 (4) | C30—C31—O29 | 111.3 (3) |
C9—C8—C10 | 103.8 (4) | C30—C31—H31 | 124.4 |
O9—C9—C8 | 111.9 (3) | O29—C31—H31 | 124.4 |
O9—C9—C1 | 124.5 (3) | C21—O32—C33 | 116.4 (2) |
C8—C9—C1 | 123.6 (3) | O32—C33—C34 | 112.4 (2) |
C9—O9—C11 | 105.2 (3) | O32—C33—H331 | 109.1 |
C11—C10—C8 | 107.1 (4) | C34—C33—H331 | 109.1 |
C11—C10—H10 | 126.4 | O32—C33—H332 | 109.1 |
C8—C10—H10 | 126.4 | C34—C33—H332 | 109.1 |
C10—C11—O9 | 112.0 (4) | H331—C33—H332 | 107.9 |
C10—C11—H11 | 124.0 | O34—C34—C33 | 107.1 (2) |
O9—C11—H11 | 124.0 | O34—C34—C35 | 109.3 (2) |
C1—O12—C13 | 116.6 (2) | C33—C34—C35 | 112.3 (2) |
O12—C13—C14 | 113.3 (2) | O34—C34—H34 | 109.4 |
O12—C13—H131 | 108.9 | C33—C34—H34 | 109.4 |
C14—C13—H131 | 108.9 | C35—C34—H34 | 109.4 |
O12—C13—H132 | 108.9 | C34—O34—C15 | 113.32 (18) |
C14—C13—H132 | 108.9 | O14—C35—C36 | 109.9 (2) |
H131—C13—H132 | 107.7 | O14—C35—C37 | 103.9 (2) |
O14—C14—C13 | 107.0 (2) | C36—C35—C37 | 111.1 (2) |
O14—C14—C15 | 109.19 (19) | O14—C35—C34 | 108.0 (2) |
C13—C14—C15 | 111.4 (2) | C36—C35—C34 | 110.5 (2) |
O14—C14—H14 | 109.7 | C37—C35—C34 | 113.2 (2) |
C13—C14—H14 | 109.7 | C35—C36—H361 | 109.5 |
C15—C14—H14 | 109.7 | C35—C36—H362 | 109.5 |
C14—O14—C35 | 113.52 (19) | H361—C36—H362 | 109.5 |
O34—C15—C16 | 109.3 (2) | C35—C36—H363 | 109.5 |
O34—C15—C17 | 103.9 (2) | H361—C36—H363 | 109.5 |
C16—C15—C17 | 111.4 (3) | H362—C36—H363 | 109.5 |
O34—C15—C14 | 108.4 (2) | C35—C37—H371 | 109.5 |
C16—C15—C14 | 110.3 (2) | C35—C37—H372 | 109.5 |
C17—C15—C14 | 113.3 (2) | H371—C37—H372 | 109.5 |
C15—C16—H161 | 109.5 | C35—C37—H373 | 109.5 |
C15—C16—H162 | 109.5 | H371—C37—H373 | 109.5 |
H161—C16—H162 | 109.5 | H372—C37—H373 | 109.5 |
C15—C16—H163 | 109.5 | C4D—N1D—C2D | 124.3 (4) |
H161—C16—H163 | 109.5 | C4D—N1D—C3D | 116.8 (4) |
H162—C16—H163 | 109.5 | C2D—N1D—C3D | 118.1 (4) |
C15—C17—H171 | 109.5 | N1D—C2D—H21D | 109.5 |
C15—C17—H172 | 109.5 | N1D—C2D—H22D | 109.5 |
H171—C17—H172 | 109.5 | H21D—C2D—H22D | 109.5 |
C15—C17—H173 | 109.5 | N1D—C2D—H23D | 109.5 |
H171—C17—H173 | 109.5 | H21D—C2D—H23D | 109.5 |
H172—C17—H173 | 109.5 | H22D—C2D—H23D | 109.5 |
O32—C21—C22 | 120.5 (3) | N1D—C3D—H31D | 109.5 |
O32—C21—C29 | 123.8 (3) | N1D—C3D—H32D | 109.5 |
C22—C21—C29 | 115.4 (3) | H31D—C3D—H32D | 109.5 |
O22—C22—C21 | 116.2 (3) | N1D—C3D—H33D | 109.5 |
O22—C22—C26 | 121.3 (3) | H31D—C3D—H33D | 109.5 |
C21—C22—C26 | 122.4 (3) | H32D—C3D—H33D | 109.5 |
C22—O22—C23 | 122.2 (3) | O4D—C4D—N1D | 132.2 (6) |
O23—C23—O22 | 116.6 (4) | O4D—C4D—H4D | 113.9 |
O23—C23—C24 | 127.2 (4) | N1D—C4D—H4D | 113.9 |
O12—C1—C2—O2 | −4.5 (4) | C21—C22—O22—C23 | 179.1 (3) |
C9—C1—C2—O2 | −176.5 (2) | C26—C22—O22—C23 | −1.5 (4) |
O12—C1—C2—C6 | 172.7 (2) | C22—O22—C23—O23 | 179.7 (3) |
C9—C1—C2—C6 | 0.7 (4) | C22—O22—C23—C24 | −0.8 (4) |
C1—C2—O2—C3 | 176.4 (3) | O23—C23—C24—C25 | −179.0 (4) |
C6—C2—O2—C3 | −0.8 (4) | O22—C23—C24—C25 | 1.5 (5) |
C2—O2—C3—O3 | −178.5 (3) | C23—C24—C25—C26 | 0.0 (5) |
C2—O2—C3—C4 | 1.8 (4) | O22—C22—C26—C27 | −178.4 (3) |
O3—C3—C4—C5 | 179.8 (4) | C21—C22—C26—C27 | 1.0 (4) |
O2—C3—C4—C5 | −0.5 (5) | O22—C22—C26—C25 | 2.9 (4) |
C3—C4—C5—C6 | −1.7 (5) | C21—C22—C26—C25 | −177.7 (3) |
O2—C2—C6—C7 | 176.7 (3) | C24—C25—C26—C27 | 179.2 (3) |
C1—C2—C6—C7 | −0.4 (4) | C24—C25—C26—C22 | −2.2 (4) |
O2—C2—C6—C5 | −1.3 (4) | C22—C26—C27—C28 | 1.3 (4) |
C1—C2—C6—C5 | −178.4 (3) | C25—C26—C27—C28 | 179.8 (3) |
C4—C5—C6—C7 | −175.4 (3) | C26—C27—C28—C29 | −2.5 (4) |
C4—C5—C6—C2 | 2.6 (5) | C26—C27—C28—C30 | 174.7 (3) |
C2—C6—C7—C8 | −0.4 (4) | O32—C21—C29—O29 | −1.5 (4) |
C5—C6—C7—C8 | 177.5 (3) | C22—C21—C29—O29 | −175.8 (2) |
C6—C7—C8—C9 | 0.7 (5) | O32—C21—C29—C28 | 174.8 (3) |
C6—C7—C8—C10 | −179.3 (4) | C22—C21—C29—C28 | 0.5 (4) |
C7—C8—C9—O9 | −179.4 (3) | C27—C28—C29—O29 | 178.4 (3) |
C10—C8—C9—O9 | 0.6 (3) | C30—C28—C29—O29 | 0.4 (3) |
C7—C8—C9—C1 | −0.4 (5) | C27—C28—C29—C21 | 1.6 (4) |
C10—C8—C9—C1 | 179.6 (3) | C30—C28—C29—C21 | −176.4 (3) |
O12—C1—C9—O9 | 6.1 (4) | C21—C29—O29—C31 | 176.3 (3) |
C2—C1—C9—O9 | 178.5 (3) | C28—C29—O29—C31 | −0.4 (3) |
O12—C1—C9—C8 | −172.8 (3) | C27—C28—C30—C31 | −177.7 (4) |
C2—C1—C9—C8 | −0.3 (4) | C29—C28—C30—C31 | −0.2 (3) |
C8—C9—O9—C11 | −0.6 (4) | C28—C30—C31—O29 | 0.0 (4) |
C1—C9—O9—C11 | −179.6 (3) | C29—O29—C31—C30 | 0.2 (3) |
C7—C8—C10—C11 | 179.6 (4) | C22—C21—O32—C33 | −125.4 (3) |
C9—C8—C10—C11 | −0.3 (4) | C29—C21—O32—C33 | 60.6 (3) |
C8—C10—C11—O9 | 0.0 (4) | C21—O32—C33—C34 | 75.2 (3) |
C9—O9—C11—C10 | 0.4 (4) | O32—C33—C34—O34 | 66.7 (3) |
C2—C1—O12—C13 | 67.4 (3) | O32—C33—C34—C35 | −173.4 (2) |
C9—C1—O12—C13 | −120.8 (3) | C33—C34—O34—C15 | −169.7 (2) |
C1—O12—C13—C14 | 75.1 (3) | C35—C34—O34—C15 | 68.4 (2) |
O12—C13—C14—O14 | 66.3 (3) | C16—C15—O34—C34 | 88.9 (3) |
O12—C13—C14—C15 | −174.4 (2) | C17—C15—O34—C34 | −152.1 (2) |
C13—C14—O14—C35 | −170.9 (2) | C14—C15—O34—C34 | −31.4 (3) |
C15—C14—O14—C35 | 68.4 (3) | C14—O14—C35—C36 | 89.2 (3) |
O14—C14—C15—O34 | −34.2 (3) | C14—O14—C35—C37 | −151.8 (2) |
C13—C14—C15—O34 | −152.2 (2) | C14—O14—C35—C34 | −31.4 (3) |
O14—C14—C15—C16 | −153.8 (2) | O34—C34—C35—O14 | −34.3 (3) |
C13—C14—C15—C16 | 88.2 (3) | C33—C34—C35—O14 | −152.9 (2) |
O14—C14—C15—C17 | 80.5 (3) | O34—C34—C35—C36 | −154.5 (2) |
C13—C14—C15—C17 | −37.5 (3) | C33—C34—C35—C36 | 86.8 (3) |
O32—C21—C22—O22 | 3.1 (4) | O34—C34—C35—C37 | 80.1 (3) |
C29—C21—C22—O22 | 177.6 (2) | C33—C34—C35—C37 | −38.5 (3) |
O32—C21—C22—C26 | −176.3 (2) | C2D—N1D—C4D—O4D | 7.3 (8) |
C29—C21—C22—C26 | −1.8 (4) | C3D—N1D—C4D—O4D | 177.4 (6) |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C32H28O10·2C2H6OS | C32H28O10·C3H7NO |
Mr | 728.80 | 645.64 |
Crystal system, space group | Orthorhombic, P212121 | Monoclinic, P21 |
Temperature (K) | 200 | 200 |
a, b, c (Å) | 10.903 (2), 13.068 (2), 24.400 (4) | 8.2000 (7), 16.2132 (14), 11.6706 (10) |
α, β, γ (°) | 90, 90, 90 | 90, 97.244 (1), 90 |
V (Å3) | 3476.5 (11) | 1539.2 (2) |
Z | 4 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.22 | 0.10 |
Crystal size (mm) | 0.50 × 0.20 × 0.04 | 0.50 × 0.40 × 0.04 |
Data collection | ||
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer | Bruker SMART APEX area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.913, 1.0 | 0.932, 1.0 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30564, 7659, 7041 | 13520, 3516, 3381 |
Rint | 0.026 | 0.017 |
(sin θ/λ)max (Å−1) | 0.641 | 0.641 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.099, 0.90 | 0.042, 0.116, 1.04 |
No. of reflections | 7659 | 3516 |
No. of parameters | 498 | 430 |
No. of restraints | 18 | 3 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.19 | 0.67, −0.38 |
Absolute structure | Flack (1983), 3379 Friedel pairs | ? |
Absolute structure parameter | 0.04 (6) | ? |
Computer programs: SMART (Bruker, 1998), SMART, SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2001).
DMSO form | DMF form | ||||
Dioxane ring | |||||
C35 | O14 | C14 | C15 | 67.6 (2) | 68.4 (3) |
O14 | C14 | C15 | O34 | -38.0 (2) | -34.2 (3) |
C14 | C15 | O34 | C34 | -26.5 (2) | -31.4 (3) |
C15 | O34 | C34 | C35 | 66.1 (2) | 68.4 (2) |
O34 | C34 | C35 | O14 | -36.4 (2) | -34.3 (3) |
C34 | C35 | O14 | C14 | -27.6 (2) | -31.4 (3) |
Ether linkage | |||||
C2 | C1 | O12 | C13 | -137.6 (2) | 67.4 (3) |
C1 | O12 | C13 | C14 | -170.7 (1) | 75.1 (3) |
O12 | C13 | C14 | O14 | 79.4 (2) | 66.3 (3) |
C22 | C21 | O32 | C33 | -146.1 (2) | -125.4 (2) |
C21 | O32 | C33 | C34 | -164.1 (2) | 75.2 (3) |
O32 | C33 | C34 | O34 | 75.0 (2) | 66.7 (3) |
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Candibirin A, (I), is a new furanocoumarin dimer isolated from Heracleum candicans WALL., which is a herbal medicine used as an antipyretic. 1H NMR and MS spectra indicated that (I) is a dimer of the previously reported furanocoumarins heraclenin, having an epoxy group (Bal-Tembeet et al., 1996), and heraclenol, having two hydroxy groups (Benkiki et al., 2002). However, the linkage structure and its chirality is unknown, since the dimerization pathway is unknown. We have therefore prepared dimethylsulfoxide (DMSO)-solvated crystals of (I) with no chemical modification (DMSO form), and the absolute configuration was determined using the anomalous dispersion effects from the DMSO S atoms. A different solvate was obtained from the dimethylformamide (DMF) solution (DMF form), where a second conformer of (I) was found.
The structure of (I) in the DMSO form is shown in Fig. 1. The two furanocoumarin moieties are linked by the dioxane ring. There are two DMSO molecules in the asymmetric unit, and one of them is disordered over two sets of sites. The R configurations of atoms C14 and C34 are evidenced by Flack (1983) parameter calculations from 3379 Friedel pairs. This configuration agrees with those previously deduced for heraclenin (Bal-Tembeet et al., 1996) and heraclenol (Benkiki et al., 2002). The presence of the dioxane ring and its configurations indicate that (I) is a dimerization product formed by reactions between the epoxy groups of heraclenin molecules.
In the DMSO form, the two furanocoumarin rings are separated from one another, and the molecule of (I) is extended. Conversely, a folded molecule is observed in the DMF form (Fig. 2). The DMF molecule is held between the two furanocoumarin rings, with an angle of approximately 25.3° (Fig. 2 inset). The plane of the DMF molecule is approximately perpendicular to those of the furanocoumarin rings. The molecular conformations of the DMSO and DMF forms seem to be very different from one another. However, when the heat of formation was calculated using the semi-empirical AM1 method implemented in MOPAC 2000 (Dewar et al., 1985) (−851.7 and −870.8 kJ mol−1 for the DMSO and DMF forms, respectively), it was found that the energy gap between these structures is only −19.1 kJ mol−1, despite the different disposition of the bulky furanocoumarin rings. To compare the conformations, molecular fitting was carried out (Fig. 3). The puckerings of the dioxane moieties are very similar to one another, and the conformational differences are mainly due to the differences betweeen the respective values of the C1—O12—C21–O32 and C22—C21—O32—C33 torsion angles (Table 1).