Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109004649/ry5026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109004649/ry5026s-cis-1sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109004649/ry5026s-trans-1sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109004649/ry50262sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109004649/ry50263sup5.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768109004649/ry5026sup6.pdf |
CCDC references: 639543; 639544; 737461; 737462
For all compounds, data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Bruker SHELXTL; PLATON (Spek,2003); software used to prepare material for publication: Bruker SHELXTL; PLATON (Spek,2003).
C44H56O6·0.44(C4H8O2) | F(000) = 1556 |
Mr = 719.59 | Dx = 1.153 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C2yc | Cell parameters from 4444 reflections |
a = 12.9673 (15) Å | θ = 2.5–26.4° |
b = 10.7883 (13) Å | µ = 0.08 mm−1 |
c = 30.264 (4) Å | T = 100 K |
β = 101.796 (1)° | Plate, orange |
V = 4144.3 (8) Å3 | 0.60 × 0.60 × 0.05 mm |
Z = 4 |
Bruker APEX CCD area detector diffractometer | 2913 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.076 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
phi and ω scans | h = −15→15 |
13064 measured reflections | k = −12→12 |
3632 independent reflections | l = −35→35 |
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)] = 0.085 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.218 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0625P)2 + 15.0678P] where P = (Fo2 + 2Fc2)/3 |
3632 reflections | (Δ/σ)max < 0.001 |
304 parameters | Δρmax = 0.54 e Å−3 |
117 restraints | Δρmin = −0.28 e Å−3 |
C44H56O6·0.44(C4H8O2) | V = 4144.3 (8) Å3 |
Mr = 719.59 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 12.9673 (15) Å | µ = 0.08 mm−1 |
b = 10.7883 (13) Å | T = 100 K |
c = 30.264 (4) Å | 0.60 × 0.60 × 0.05 mm |
β = 101.796 (1)° |
Bruker APEX CCD area detector diffractometer | 2913 reflections with I > 2σ(I) |
13064 measured reflections | Rint = 0.076 |
3632 independent reflections |
R[F2 > 2σ(F2)] = 0.085 | 117 restraints |
wR(F2) = 0.218 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0625P)2 + 15.0678P] where P = (Fo2 + 2Fc2)/3 |
3632 reflections | Δρmax = 0.54 e Å−3 |
304 parameters | Δρmin = −0.28 e Å−3 |
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) | |
O3 | 0.8438 (2) | 0.5392 (4) | 0.76819 (10) | 0.0500 (10) | 0.743 (4) |
O4 | 0.6749 (3) | 0.6950 (6) | 0.75060 (14) | 0.0599 (13) | 0.743 (4) |
O21 | 0.7427 (3) | 0.4588 (7) | 0.81238 (14) | 0.0756 (15) | 0.743 (4) |
C1 | 0.7275 (3) | 0.4789 (4) | 0.64577 (11) | 0.0438 (9) | 0.743 (4) |
C2 | 0.8081 (4) | 0.5029 (8) | 0.68898 (18) | 0.0405 (14) | 0.743 (4) |
H2A | 0.8608 | 0.4352 | 0.6933 | 0.049* | 0.743 (4) |
H2B | 0.8456 | 0.5812 | 0.6857 | 0.049* | 0.743 (4) |
C3 | 0.7618 (4) | 0.5114 (5) | 0.72946 (15) | 0.0462 (11) | 0.743 (4) |
H3 | 0.7279 | 0.4307 | 0.7343 | 0.055* | 0.743 (4) |
C4 | 0.6796 (4) | 0.6138 (6) | 0.72271 (16) | 0.0457 (13) | 0.743 (4) |
C21 | 0.8211 (5) | 0.5079 (6) | 0.80802 (18) | 0.0496 (13) | 0.743 (4) |
C22 | 0.9124 (4) | 0.5375 (5) | 0.84551 (16) | 0.0503 (13) | 0.743 (4) |
H22A | 0.8883 | 0.5411 | 0.8741 | 0.075* | 0.743 (4) |
H22B | 0.9423 | 0.6178 | 0.8397 | 0.075* | 0.743 (4) |
H22C | 0.9663 | 0.4730 | 0.8472 | 0.075* | 0.743 (4) |
O3B | 0.8679 (7) | 0.7147 (9) | 0.7386 (3) | 0.046 (3)* | 0.257 (4) |
O4B | 0.6627 (11) | 0.7507 (12) | 0.7393 (4) | 0.051 (4)* | 0.257 (4) |
O21B | 0.9789 (9) | 0.7782 (11) | 0.6958 (4) | 0.058 (3)* | 0.257 (4) |
C1B | 0.7275 (3) | 0.4789 (4) | 0.64577 (11) | 0.0438 (9) | 0.257 (4) |
C2B | 0.8039 (15) | 0.5405 (15) | 0.6861 (6) | 0.038 (6)* | 0.257 (4) |
H2D | 0.8011 | 0.4898 | 0.7131 | 0.046* | 0.257 (4) |
H2E | 0.8758 | 0.5307 | 0.6802 | 0.046* | 0.257 (4) |
C3B | 0.7942 (9) | 0.6733 (11) | 0.6995 (4) | 0.038 (3)* | 0.257 (4) |
H3B | 0.8021 | 0.7270 | 0.6735 | 0.046* | 0.257 (4) |
C4B | 0.6841 (9) | 0.6913 (14) | 0.7080 (5) | 0.038 (3)* | 0.257 (4) |
C21B | 0.9549 (10) | 0.7718 (14) | 0.7303 (4) | 0.039 (3)* | 0.257 (4) |
C22B | 1.0088 (14) | 0.8293 (18) | 0.7739 (5) | 0.055 (4)* | 0.257 (4) |
H22D | 1.0709 | 0.7799 | 0.7872 | 0.083* | 0.257 (4) |
H22E | 0.9602 | 0.8320 | 0.7947 | 0.083* | 0.257 (4) |
H22F | 1.0308 | 0.9137 | 0.7682 | 0.083* | 0.257 (4) |
C5 | 0.5996 (3) | 0.6111 (4) | 0.67832 (13) | 0.0465 (10) | |
C6 | 0.6200 (2) | 0.5380 (3) | 0.64475 (11) | 0.0340 (8) | |
C7 | 0.5385 (2) | 0.5087 (3) | 0.60463 (10) | 0.0285 (7) | |
H7 | 0.5563 | 0.5194 | 0.5759 | 0.034* | |
C8 | 0.4415 (2) | 0.4683 (3) | 0.60543 (11) | 0.0310 (7) | |
H8 | 0.4235 | 0.4599 | 0.6342 | 0.037* | |
C9 | 0.3610 (2) | 0.4362 (3) | 0.56609 (10) | 0.0279 (7) | |
C10 | 0.2652 (2) | 0.3960 (3) | 0.57222 (11) | 0.0315 (7) | |
H10 | 0.2575 | 0.3832 | 0.6024 | 0.038* | |
C11 | 0.1752 (2) | 0.3712 (3) | 0.53719 (11) | 0.0298 (7) | |
H11 | 0.1828 | 0.3822 | 0.5069 | 0.036* | |
C12 | 0.0804 (2) | 0.3333 (3) | 0.54402 (11) | 0.0289 (7) | |
H12 | 0.0753 | 0.3136 | 0.5741 | 0.035* | |
C13 | −0.0138 (2) | 0.3203 (3) | 0.50945 (10) | 0.0278 (7) | |
C14 | −0.1055 (2) | 0.2856 (3) | 0.52153 (11) | 0.0291 (7) | |
H14 | −0.1013 | 0.2693 | 0.5527 | 0.035* | |
C15 | −0.2070 (2) | 0.2707 (3) | 0.49289 (11) | 0.0293 (7) | |
H15 | −0.2145 | 0.2914 | 0.4619 | 0.035* | |
C16 | 0.7122 (5) | 0.3328 (5) | 0.6457 (2) | 0.0474 (13) | 0.743 (4) |
H16A | 0.7788 | 0.2921 | 0.6439 | 0.071* | 0.743 (4) |
H16B | 0.6577 | 0.3087 | 0.6197 | 0.071* | 0.743 (4) |
H16C | 0.6907 | 0.3074 | 0.6736 | 0.071* | 0.743 (4) |
C17 | 0.7701 (4) | 0.5087 (8) | 0.60408 (16) | 0.0474 (14) | 0.743 (4) |
H17A | 0.8415 | 0.4750 | 0.6074 | 0.071* | 0.743 (4) |
H17B | 0.7721 | 0.5988 | 0.6002 | 0.071* | 0.743 (4) |
H17C | 0.7244 | 0.4717 | 0.5776 | 0.071* | 0.743 (4) |
C16B | 0.723 (3) | 0.3478 (19) | 0.6298 (11) | 0.112 (14)* | 0.257 (4) |
H16D | 0.6493 | 0.3253 | 0.6173 | 0.168* | 0.257 (4) |
H16E | 0.7512 | 0.2930 | 0.6552 | 0.168* | 0.257 (4) |
H16F | 0.7643 | 0.3390 | 0.6064 | 0.168* | 0.257 (4) |
C17B | 0.774 (2) | 0.566 (2) | 0.6114 (8) | 0.074 (8)* | 0.257 (4) |
H17D | 0.7871 | 0.6495 | 0.6243 | 0.110* | 0.257 (4) |
H17E | 0.7238 | 0.5710 | 0.5826 | 0.110* | 0.257 (4) |
H17F | 0.8409 | 0.5312 | 0.6065 | 0.110* | 0.257 (4) |
C18 | 0.4987 (3) | 0.6817 (4) | 0.67708 (13) | 0.0500 (10) | |
H18A | 0.4617 | 0.6924 | 0.6457 | 0.075* | |
H18B | 0.5149 | 0.7632 | 0.6911 | 0.075* | |
H18C | 0.4538 | 0.6354 | 0.6937 | 0.075* | |
C19 | 0.3862 (2) | 0.4522 (3) | 0.52046 (10) | 0.0304 (7) | |
H19A | 0.3309 | 0.4135 | 0.4977 | 0.046* | |
H19B | 0.4540 | 0.4129 | 0.5199 | 0.046* | |
H19C | 0.3902 | 0.5408 | 0.5138 | 0.046* | |
C20 | −0.0072 (2) | 0.3484 (3) | 0.46176 (11) | 0.0324 (7) | |
H20A | −0.0771 | 0.3397 | 0.4423 | 0.049* | |
H20B | 0.0418 | 0.2904 | 0.4519 | 0.049* | |
H20C | 0.0182 | 0.4334 | 0.4598 | 0.049* | |
O1S | 0.5479 (16) | 0.325 (2) | 0.7471 (7) | 0.152 (10)* | 0.22 |
O2S | 0.6797 (14) | 0.4532 (16) | 0.7699 (6) | 0.106 (6)* | 0.22 |
C1S | 0.6170 (16) | 0.3579 (19) | 0.7746 (6) | 0.104 (9)* | 0.22 |
C2S | 0.6516 (17) | 0.3024 (19) | 0.8190 (6) | 0.071 (6)* | 0.22 |
H2S1 | 0.6027 | 0.2361 | 0.8232 | 0.107* | 0.22 |
H2S2 | 0.6528 | 0.3658 | 0.8423 | 0.107* | 0.22 |
H2S3 | 0.7224 | 0.2679 | 0.8215 | 0.107* | 0.22 |
C3S | 0.746 (3) | 0.512 (3) | 0.8059 (13) | 0.22 (4)* | 0.22 |
H3S1 | 0.7149 | 0.5018 | 0.8329 | 0.260* | 0.22 |
H3S2 | 0.7446 | 0.6021 | 0.7990 | 0.260* | 0.22 |
C4S | 0.859 (3) | 0.475 (5) | 0.8190 (16) | 0.15 (2)* | 0.22 |
H4S1 | 0.8983 | 0.5390 | 0.8387 | 0.231* | 0.22 |
H4S2 | 0.8887 | 0.4668 | 0.7919 | 0.231* | 0.22 |
H4S3 | 0.8646 | 0.3961 | 0.8351 | 0.231* | 0.22 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0348 (17) | 0.081 (3) | 0.0312 (15) | 0.0048 (17) | −0.0013 (13) | −0.0064 (16) |
O4 | 0.045 (2) | 0.091 (4) | 0.040 (2) | 0.005 (2) | −0.0026 (17) | −0.027 (2) |
O21 | 0.052 (3) | 0.131 (5) | 0.043 (2) | −0.007 (2) | 0.0074 (18) | 0.002 (3) |
C1 | 0.0272 (16) | 0.069 (2) | 0.0323 (17) | 0.0071 (17) | −0.0002 (13) | −0.0107 (17) |
C2 | 0.028 (3) | 0.056 (4) | 0.032 (2) | 0.012 (2) | −0.0059 (16) | −0.003 (3) |
C3 | 0.036 (2) | 0.065 (3) | 0.033 (2) | 0.001 (2) | −0.0014 (17) | −0.002 (2) |
C4 | 0.033 (2) | 0.073 (4) | 0.031 (2) | 0.003 (2) | 0.0056 (18) | −0.011 (2) |
C21 | 0.043 (3) | 0.070 (4) | 0.032 (2) | 0.007 (3) | 0.000 (2) | −0.010 (2) |
C22 | 0.061 (3) | 0.052 (3) | 0.031 (2) | 0.003 (3) | −0.006 (2) | −0.006 (2) |
C1B | 0.0272 (16) | 0.069 (2) | 0.0323 (17) | 0.0071 (17) | −0.0002 (13) | −0.0107 (17) |
C5 | 0.0281 (17) | 0.065 (3) | 0.045 (2) | −0.0028 (17) | 0.0043 (15) | −0.0190 (19) |
C6 | 0.0266 (16) | 0.0411 (19) | 0.0332 (17) | −0.0021 (14) | 0.0036 (13) | −0.0021 (14) |
C7 | 0.0295 (16) | 0.0248 (16) | 0.0302 (16) | 0.0030 (13) | 0.0036 (13) | 0.0012 (13) |
C8 | 0.0295 (16) | 0.0304 (17) | 0.0317 (16) | 0.0000 (14) | 0.0028 (13) | 0.0037 (13) |
C9 | 0.0274 (16) | 0.0207 (15) | 0.0342 (17) | 0.0020 (13) | 0.0030 (13) | 0.0012 (13) |
C10 | 0.0325 (17) | 0.0267 (16) | 0.0342 (17) | −0.0005 (14) | 0.0043 (13) | 0.0015 (13) |
C11 | 0.0313 (16) | 0.0219 (16) | 0.0353 (17) | 0.0014 (13) | 0.0048 (13) | −0.0016 (13) |
C12 | 0.0285 (16) | 0.0210 (15) | 0.0363 (17) | 0.0007 (13) | 0.0044 (13) | −0.0025 (13) |
C13 | 0.0277 (16) | 0.0156 (14) | 0.0388 (18) | 0.0016 (12) | 0.0038 (13) | −0.0069 (12) |
C14 | 0.0301 (16) | 0.0182 (14) | 0.0379 (17) | 0.0008 (13) | 0.0044 (13) | −0.0041 (13) |
C15 | 0.0299 (16) | 0.0179 (14) | 0.0386 (17) | 0.0015 (12) | 0.0036 (13) | −0.0049 (13) |
C16 | 0.042 (3) | 0.059 (3) | 0.036 (3) | 0.027 (2) | −0.007 (2) | −0.015 (2) |
C17 | 0.023 (2) | 0.088 (5) | 0.030 (2) | 0.009 (3) | 0.0030 (18) | −0.012 (3) |
C18 | 0.042 (2) | 0.054 (2) | 0.052 (2) | 0.0042 (19) | 0.0061 (17) | −0.0153 (19) |
C19 | 0.0263 (16) | 0.0255 (16) | 0.0373 (17) | −0.0011 (13) | 0.0016 (13) | −0.0039 (13) |
C20 | 0.0287 (16) | 0.0251 (16) | 0.0410 (18) | −0.0017 (13) | 0.0012 (13) | −0.0037 (14) |
O3—C21 | 1.341 (7) | C11—C12 | 1.351 (4) |
O3—C3 | 1.444 (5) | C11—H11 | 0.9500 |
O4—C4 | 1.227 (6) | C12—C13 | 1.443 (4) |
O21—C21 | 1.178 (8) | C12—H12 | 0.9500 |
C1—C17 | 1.512 (6) | C13—C14 | 1.366 (4) |
C1—C2 | 1.520 (6) | C13—C20 | 1.494 (4) |
C1—C6 | 1.528 (5) | C14—C15 | 1.429 (4) |
C1—C16 | 1.589 (7) | C14—H14 | 0.9500 |
C2—C3 | 1.473 (8) | C15—C15ii | 1.351 (6) |
C2—H2A | 0.9900 | C15—H15 | 0.9500 |
C2—H2B | 0.9900 | C16—H16A | 0.9800 |
C3—C4 | 1.520 (7) | C16—H16B | 0.9800 |
C3—H3 | 1.0000 | C16—H16C | 0.9800 |
C4—C5 | 1.521 (6) | C17—H17A | 0.9800 |
C21—C22 | 1.497 (7) | C17—H17B | 0.9800 |
C22—H22A | 0.9800 | C17—H17C | 0.9800 |
C22—H22B | 0.9800 | C16B—H16D | 0.9800 |
C22—H22C | 0.9800 | C16B—H16E | 0.9800 |
O3B—C21B | 1.352 (14) | C16B—H16F | 0.9800 |
O3B—C3B | 1.432 (12) | C17B—H17D | 0.9800 |
O4B—C4B | 1.222 (14) | C17B—H17E | 0.9800 |
O21B—C22Bi | 1.05 (2) | C17B—H17F | 0.9800 |
O21B—C21B | 1.151 (14) | C18—H18A | 0.9800 |
C2B—C3B | 1.501 (15) | C18—H18B | 0.9800 |
C2B—H2D | 0.9900 | C18—H18C | 0.9800 |
C2B—H2E | 0.9900 | C19—H19A | 0.9800 |
C3B—C4B | 1.514 (14) | C19—H19B | 0.9800 |
C3B—H3B | 1.0000 | C19—H19C | 0.9800 |
C4B—C5 | 1.535 (13) | C20—H20A | 0.9800 |
C21B—C22Bi | 0.805 (19) | C20—H20B | 0.9800 |
C21B—C22B | 1.494 (15) | C20—H20C | 0.9800 |
C21B—C21Bi | 1.49 (2) | O1S—C1S | 1.148 (14) |
C22B—H22D | 0.9800 | O1S—O1Siii | 1.29 (5) |
C22B—H22E | 0.9800 | O2S—C1S | 1.337 (15) |
C22B—H22F | 0.9800 | O2S—C3S | 1.399 (19) |
C5—C6 | 1.354 (5) | C1S—C2S | 1.457 (13) |
C5—C18 | 1.508 (5) | C2S—H2S1 | 0.9800 |
C6—C7 | 1.471 (4) | C2S—H2S2 | 0.9800 |
C7—C8 | 1.336 (4) | C2S—H2S3 | 0.9800 |
C7—H7 | 0.9500 | C3S—C4S | 1.489 (15) |
C8—C9 | 1.456 (4) | C3S—H3S1 | 0.9900 |
C8—H8 | 0.9500 | C3S—H3S2 | 0.9900 |
C9—C10 | 1.364 (4) | C4S—H4S1 | 0.9800 |
C9—C19 | 1.493 (4) | C4S—H4S2 | 0.9800 |
C10—C11 | 1.432 (4) | C4S—H4S3 | 0.9800 |
C10—H10 | 0.9500 | ||
C21—O3—C3 | 114.7 (4) | C9—C8—H8 | 117.2 |
C17—C1—C2 | 112.2 (4) | C10—C9—C8 | 119.0 (3) |
C17—C1—C6 | 112.4 (3) | C10—C9—C19 | 122.7 (3) |
C2—C1—C6 | 114.2 (4) | C8—C9—C19 | 118.2 (3) |
C17—C1—C16 | 106.1 (5) | C9—C10—C11 | 125.8 (3) |
C2—C1—C16 | 103.5 (4) | C9—C10—H10 | 117.1 |
C6—C1—C16 | 107.5 (3) | C11—C10—H10 | 117.1 |
C3—C2—C1 | 113.6 (4) | C12—C11—C10 | 124.9 (3) |
C3—C2—H2A | 108.8 | C12—C11—H11 | 117.5 |
C1—C2—H2A | 108.8 | C10—C11—H11 | 117.5 |
C3—C2—H2B | 108.8 | C11—C12—C13 | 125.5 (3) |
C1—C2—H2B | 108.8 | C11—C12—H12 | 117.3 |
H2A—C2—H2B | 107.7 | C13—C12—H12 | 117.3 |
O3—C3—C2 | 109.3 (4) | C14—C13—C12 | 119.1 (3) |
O3—C3—C4 | 109.7 (4) | C14—C13—C20 | 122.6 (3) |
C2—C3—C4 | 109.1 (5) | C12—C13—C20 | 118.2 (3) |
O3—C3—H3 | 109.6 | C13—C14—C15 | 127.8 (3) |
C2—C3—H3 | 109.6 | C13—C14—H14 | 116.1 |
C4—C3—H3 | 109.6 | C15—C14—H14 | 116.1 |
O4—C4—C3 | 124.0 (5) | C15ii—C15—C14 | 124.2 (4) |
O4—C4—C5 | 120.0 (5) | C15ii—C15—H15 | 117.9 |
C3—C4—C5 | 116.0 (4) | C14—C15—H15 | 117.9 |
O21—C21—O3 | 124.5 (5) | H16D—C16B—H16E | 109.5 |
O21—C21—C22 | 125.3 (5) | H16D—C16B—H16F | 109.5 |
O3—C21—C22 | 110.1 (5) | H16E—C16B—H16F | 109.5 |
C21B—O3B—C3B | 115.5 (9) | H17D—C17B—H17E | 109.5 |
C22Bi—O21B—C21B | 42.5 (11) | H17D—C17B—H17F | 109.5 |
C3B—C2B—H2D | 106.6 | H17E—C17B—H17F | 109.5 |
C3B—C2B—H2E | 106.6 | C5—C18—H18A | 109.5 |
H2D—C2B—H2E | 106.5 | C5—C18—H18B | 109.5 |
O3B—C3B—C2B | 116.2 (11) | H18A—C18—H18B | 109.5 |
O3B—C3B—C4B | 108.2 (9) | C5—C18—H18C | 109.5 |
C2B—C3B—C4B | 107.6 (12) | H18A—C18—H18C | 109.5 |
O3B—C3B—H3B | 108.2 | H18B—C18—H18C | 109.5 |
C2B—C3B—H3B | 108.2 | C9—C19—H19A | 109.5 |
C4B—C3B—H3B | 108.2 | C9—C19—H19B | 109.5 |
O4B—C4B—C3B | 124.8 (12) | H19A—C19—H19B | 109.5 |
O4B—C4B—C5 | 120.0 (11) | C9—C19—H19C | 109.5 |
C3B—C4B—C5 | 114.5 (9) | H19A—C19—H19C | 109.5 |
C22Bi—C21B—O21B | 62.2 (16) | H19B—C19—H19C | 109.5 |
C22Bi—C21B—O3B | 157 (2) | C13—C20—H20A | 109.5 |
O21B—C21B—O3B | 125.9 (12) | C13—C20—H20B | 109.5 |
C22Bi—C21B—C22B | 69 (2) | H20A—C20—H20B | 109.5 |
O21B—C21B—C22B | 127.6 (14) | C13—C20—H20C | 109.5 |
O3B—C21B—C22B | 106.5 (11) | H20A—C20—H20C | 109.5 |
C22Bi—C21B—C21Bi | 74.8 (16) | H20B—C20—H20C | 109.5 |
O21B—C21B—C21Bi | 114.2 (15) | C1S—O1S—O1Siii | 122 (3) |
O3B—C21B—C21Bi | 113.7 (12) | C1S—O2S—C3S | 124.1 (19) |
C22B—C21B—C21Bi | 31.3 (8) | O1S—C1S—O2S | 124.3 (13) |
C21B—C22B—H22D | 109.5 | O1S—C1S—C2S | 126.1 (14) |
C21B—C22B—H22E | 109.5 | O2S—C1S—C2S | 109.5 (11) |
H22D—C22B—H22E | 109.5 | C1S—C2S—H2S1 | 109.5 |
C21B—C22B—H22F | 109.5 | C1S—C2S—H2S2 | 109.5 |
H22D—C22B—H22F | 109.5 | H2S1—C2S—H2S2 | 109.5 |
H22E—C22B—H22F | 109.5 | C1S—C2S—H2S3 | 109.5 |
C6—C5—C18 | 125.3 (3) | H2S1—C2S—H2S3 | 109.5 |
C6—C5—C4 | 118.1 (3) | H2S2—C2S—H2S3 | 109.5 |
C18—C5—C4 | 116.4 (3) | O2S—C3S—C4S | 120 (3) |
C6—C5—C4B | 122.8 (5) | O2S—C3S—H3S1 | 107.3 |
C18—C5—C4B | 104.0 (5) | C4S—C3S—H3S1 | 107.3 |
C4—C5—C4B | 36.4 (6) | O2S—C3S—H3S2 | 107.3 |
C5—C6—C7 | 121.8 (3) | C4S—C3S—H3S2 | 107.3 |
C5—C6—C1 | 123.1 (3) | H3S1—C3S—H3S2 | 106.9 |
C7—C6—C1 | 115.2 (3) | C3S—C4S—H4S1 | 109.5 |
C8—C7—C6 | 125.1 (3) | C3S—C4S—H4S2 | 109.5 |
C8—C7—H7 | 117.5 | H4S1—C4S—H4S2 | 109.5 |
C6—C7—H7 | 117.5 | C3S—C4S—H4S3 | 109.5 |
C7—C8—C9 | 125.7 (3) | H4S1—C4S—H4S3 | 109.5 |
C7—C8—H8 | 117.2 | H4S2—C4S—H4S3 | 109.5 |
C17—C1—C2—C3 | 162.7 (6) | C3B—C4B—C5—C18 | −155.5 (10) |
C6—C1—C2—C3 | 33.2 (8) | O4B—C4B—C5—C4 | −82.3 (15) |
C16—C1—C2—C3 | −83.4 (7) | C3B—C4B—C5—C4 | 88.8 (13) |
C21—O3—C3—C2 | −158.0 (6) | C18—C5—C6—C7 | −7.2 (6) |
C21—O3—C3—C4 | 82.4 (6) | C4—C5—C6—C7 | 166.8 (4) |
C1—C2—C3—O3 | −177.7 (5) | C4B—C5—C6—C7 | −151.0 (8) |
C1—C2—C3—C4 | −57.7 (7) | C18—C5—C6—C1 | 173.7 (4) |
O3—C3—C4—O4 | −11.8 (8) | C4—C5—C6—C1 | −12.4 (6) |
C2—C3—C4—O4 | −131.6 (6) | C4B—C5—C6—C1 | 29.8 (9) |
O3—C3—C4—C5 | 168.6 (4) | C17—C1—C6—C5 | −126.0 (5) |
C2—C3—C4—C5 | 48.9 (6) | C2—C1—C6—C5 | 3.4 (6) |
C3—O3—C21—O21 | 1.8 (9) | C16—C1—C6—C5 | 117.6 (4) |
C3—O3—C21—C22 | 178.4 (5) | C17—C1—C6—C7 | 54.8 (5) |
C21B—O3B—C3B—C2B | 95.3 (16) | C2—C1—C6—C7 | −175.9 (4) |
C21B—O3B—C3B—C4B | −143.5 (12) | C16—C1—C6—C7 | −61.6 (4) |
O3B—C3B—C4B—O4B | 12 (2) | C5—C6—C7—C8 | −49.1 (5) |
C2B—C3B—C4B—O4B | 138.1 (17) | C1—C6—C7—C8 | 130.2 (4) |
O3B—C3B—C4B—C5 | −158.8 (10) | C6—C7—C8—C9 | −178.4 (3) |
C2B—C3B—C4B—C5 | −32.5 (16) | C7—C8—C9—C10 | 179.9 (3) |
C22Bi—O21B—C21B—O3B | 154 (3) | C7—C8—C9—C19 | −1.8 (5) |
C22Bi—O21B—C21B—C22B | −22.5 (18) | C8—C9—C10—C11 | 174.2 (3) |
C22Bi—O21B—C21B—C21Bi | −55.7 (16) | C19—C9—C10—C11 | −4.0 (5) |
C3B—O3B—C21B—C22Bi | 94 (5) | C9—C10—C11—C12 | −178.8 (3) |
C3B—O3B—C21B—O21B | −8 (2) | C10—C11—C12—C13 | 173.2 (3) |
C3B—O3B—C21B—C22B | 168.7 (11) | C11—C12—C13—C14 | −177.5 (3) |
C3B—O3B—C21B—C21Bi | −158.8 (9) | C11—C12—C13—C20 | 1.2 (4) |
O4—C4—C5—C6 | 166.0 (5) | C12—C13—C14—C15 | 178.3 (3) |
C3—C4—C5—C6 | −14.4 (7) | C20—C13—C14—C15 | −0.4 (5) |
O4—C4—C5—C18 | −19.5 (7) | C13—C14—C15—C15ii | 176.2 (4) |
C3—C4—C5—C18 | 160.1 (4) | O1Siii—O1S—C1S—O2S | −119 (2) |
O4—C4—C5—C4B | 58.0 (9) | O1Siii—O1S—C1S—C2S | 62 (2) |
C3—C4—C5—C4B | −122.5 (9) | C3S—O2S—C1S—O1S | 164 (3) |
O4B—C4B—C5—C6 | −176.4 (11) | C3S—O2S—C1S—C2S | −17 (3) |
C3B—C4B—C5—C6 | −5.3 (15) | C1S—O2S—C3S—C4S | 96 (4) |
O4B—C4B—C5—C18 | 33.4 (15) |
Symmetry codes: (i) −x+2, y, −z+3/2; (ii) −x−1/2, −y+1/2, −z+1; (iii) −x+1, y, −z+3/2. |
C44H56O6 | F(000) = 736 |
Mr = 680.89 | Dx = 1.161 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 3456 reflections |
a = 10.6598 (10) Å | θ = 2.3–26.2° |
b = 10.1683 (10) Å | µ = 0.08 mm−1 |
c = 18.2940 (18) Å | T = 100 K |
β = 100.700 (2)° | Plate, red |
V = 1948.4 (3) Å3 | 0.60 × 0.60 × 0.10 mm |
Z = 2 |
Bruker APEX CCD area detector diffractometer | 2506 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.072 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
phi and ω scans | h = −12→11 |
9816 measured reflections | k = −9→12 |
3425 independent reflections | l = −21→21 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.175 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0489P)2 + 1.5414P] where P = (Fo2 + 2Fc2)/3 |
3425 reflections | (Δ/σ)max = 0.001 |
305 parameters | Δρmax = 0.39 e Å−3 |
73 restraints | Δρmin = −0.21 e Å−3 |
C44H56O6 | V = 1948.4 (3) Å3 |
Mr = 680.89 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.6598 (10) Å | µ = 0.08 mm−1 |
b = 10.1683 (10) Å | T = 100 K |
c = 18.2940 (18) Å | 0.60 × 0.60 × 0.10 mm |
β = 100.700 (2)° |
Bruker APEX CCD area detector diffractometer | 2506 reflections with I > 2σ(I) |
9816 measured reflections | Rint = 0.072 |
3425 independent reflections |
R[F2 > 2σ(F2)] = 0.065 | 73 restraints |
wR(F2) = 0.175 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.39 e Å−3 |
3425 reflections | Δρmin = −0.21 e Å−3 |
305 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 | Occ. (<1) | |
O4 | 0.86809 (19) | −0.07034 (18) | 0.34294 (10) | 0.0525 (5) | |
O3 | 1.0473 (3) | 0.1135 (3) | 0.35298 (15) | 0.0504 (7) | 0.788 (4) |
O21 | 0.9139 (2) | 0.2207 (3) | 0.41407 (15) | 0.0608 (8) | 0.788 (4) |
C1 | 0.9199 (5) | 0.1090 (6) | 0.1462 (3) | 0.0412 (14) | 0.788 (4) |
C2 | 1.0123 (2) | 0.1161 (2) | 0.22110 (13) | 0.0523 (10) | 0.788 (4) |
H2A | 1.0743 | 0.0430 | 0.2235 | 0.063* | 0.788 (4) |
H2B | 1.0608 | 0.1994 | 0.2230 | 0.063* | 0.788 (4) |
C3 | 0.9532 (2) | 0.1091 (2) | 0.28575 (13) | 0.0574 (8) | 0.788 (4) |
H3 | 0.8959 | 0.1872 | 0.2852 | 0.069* | 0.788 (4) |
C16 | 1.0070 (5) | 0.0802 (6) | 0.0901 (3) | 0.0500 (12) | 0.788 (4) |
H16A | 0.9607 | 0.0982 | 0.0396 | 0.075* | 0.788 (4) |
H16B | 1.0330 | −0.0124 | 0.0939 | 0.075* | 0.788 (4) |
H16C | 1.0829 | 0.1363 | 0.1009 | 0.075* | 0.788 (4) |
C17 | 0.8510 (7) | 0.2415 (7) | 0.1283 (3) | 0.0490 (13) | 0.788 (4) |
H17A | 0.7949 | 0.2364 | 0.0795 | 0.073* | 0.788 (4) |
H17B | 0.9143 | 0.3112 | 0.1278 | 0.073* | 0.788 (4) |
H17C | 0.8000 | 0.2612 | 0.1664 | 0.073* | 0.788 (4) |
C21 | 1.0126 (4) | 0.1660 (4) | 0.4135 (2) | 0.0477 (9) | 0.788 (4) |
C22 | 1.1163 (10) | 0.1437 (11) | 0.4793 (3) | 0.0541 (17) | 0.788 (4) |
H22A | 1.1852 | 0.0927 | 0.4641 | 0.081* | 0.788 (4) |
H22B | 1.0821 | 0.0952 | 0.5175 | 0.081* | 0.788 (4) |
H22C | 1.1498 | 0.2286 | 0.4995 | 0.081* | 0.788 (4) |
O3B | 0.9884 (16) | 0.1680 (13) | 0.3577 (6) | 0.086 (4) | 0.212 (4) |
O21B | 1.1647 (12) | 0.0432 (13) | 0.3953 (7) | 0.092 (4) | 0.212 (4) |
C1B | 0.8923 (19) | 0.143 (2) | 0.1490 (8) | 0.033 (4) | 0.212 (4) |
C2B | 0.9304 (11) | 0.1951 (10) | 0.2280 (5) | 0.034 (2) | 0.212 (4) |
H2C | 1.0084 | 0.2488 | 0.2299 | 0.041* | 0.212 (4) |
H2D | 0.8620 | 0.2555 | 0.2371 | 0.041* | 0.212 (4) |
C3B | 0.9532 (2) | 0.1091 (2) | 0.28575 (13) | 0.0574 (8) | 0.212 (4) |
H3B | 1.0366 | 0.0706 | 0.2789 | 0.069* | 0.212 (4) |
C16B | 1.0126 (17) | 0.103 (2) | 0.1221 (8) | 0.038 (4) | 0.212 (4) |
H16D | 0.9920 | 0.0826 | 0.0689 | 0.056* | 0.212 (4) |
H16E | 1.0494 | 0.0251 | 0.1496 | 0.056* | 0.212 (4) |
H16F | 1.0743 | 0.1753 | 0.1305 | 0.056* | 0.212 (4) |
C17B | 0.825 (2) | 0.2538 (19) | 0.0996 (10) | 0.039 (4) | 0.212 (4) |
H17D | 0.8135 | 0.2274 | 0.0472 | 0.059* | 0.212 (4) |
H17E | 0.8769 | 0.3338 | 0.1073 | 0.059* | 0.212 (4) |
H17F | 0.7413 | 0.2709 | 0.1126 | 0.059* | 0.212 (4) |
C21B | 1.0830 (16) | 0.1169 (16) | 0.4087 (9) | 0.067 (4) | 0.212 (4) |
C22B | 1.084 (4) | 0.171 (4) | 0.4838 (13) | 0.084 (15) | 0.212 (4) |
H22D | 1.0070 | 0.1428 | 0.5013 | 0.125* | 0.212 (4) |
H22E | 1.0867 | 0.2672 | 0.4818 | 0.125* | 0.212 (4) |
H22F | 1.1597 | 0.1386 | 0.5180 | 0.125* | 0.212 (4) |
C4 | 0.8740 (2) | −0.0121 (3) | 0.28521 (15) | 0.0440 (6) | |
C5 | 0.8007 (2) | −0.0538 (2) | 0.21228 (15) | 0.0402 (6) | |
C6 | 0.8172 (2) | 0.0049 (3) | 0.14774 (15) | 0.0431 (6) | |
C7 | 0.7383 (2) | −0.0415 (3) | 0.07905 (15) | 0.0476 (7) | |
H7 | 0.6825 | −0.1119 | 0.0852 | 0.057* | |
C8 | 0.7310 (2) | −0.0012 (3) | 0.00776 (15) | 0.0425 (6) | |
H8 | 0.7853 | 0.0686 | −0.0014 | 0.051* | |
C9 | 0.6457 (2) | −0.0577 (3) | −0.05540 (15) | 0.0449 (7) | |
C10 | 0.6507 (2) | −0.0112 (3) | −0.12432 (15) | 0.0442 (6) | |
H10 | 0.7107 | 0.0568 | −0.1272 | 0.053* | |
C11 | 0.5747 (2) | −0.0542 (3) | −0.19332 (16) | 0.0457 (7) | |
H11 | 0.5099 | −0.1176 | −0.1915 | 0.055* | |
C12 | 0.5898 (3) | −0.0100 (3) | −0.26051 (15) | 0.0469 (7) | |
H12 | 0.6564 | 0.0516 | −0.2617 | 0.056* | |
C13 | 0.5128 (3) | −0.0487 (3) | −0.33144 (16) | 0.0481 (7) | |
C14 | 0.5442 (3) | 0.0002 (3) | −0.39485 (16) | 0.0500 (7) | |
H14 | 0.6155 | 0.0579 | −0.3889 | 0.060* | |
C15 | 0.4814 (3) | −0.0260 (3) | −0.46986 (15) | 0.0518 (7) | |
H15 | 0.4095 | −0.0830 | −0.4774 | 0.062* | |
C18 | 0.7081 (3) | −0.1646 (3) | 0.21580 (16) | 0.0498 (7) | |
H18A | 0.6217 | −0.1362 | 0.1934 | 0.075* | |
H18B | 0.7103 | −0.1891 | 0.2678 | 0.075* | |
H18C | 0.7321 | −0.2406 | 0.1885 | 0.075* | |
C19 | 0.5587 (3) | −0.1675 (3) | −0.04230 (16) | 0.0545 (8) | |
H19A | 0.5012 | −0.1892 | −0.0890 | 0.082* | |
H19B | 0.5083 | −0.1401 | −0.0053 | 0.082* | |
H19C | 0.6096 | −0.2451 | −0.0240 | 0.082* | |
C20 | 0.4038 (3) | −0.1426 (3) | −0.33138 (17) | 0.0558 (8) | |
H20A | 0.3506 | −0.1457 | −0.3812 | 0.084* | |
H20B | 0.3522 | −0.1128 | −0.2955 | 0.084* | |
H20C | 0.4376 | −0.2306 | −0.3175 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0581 (12) | 0.0456 (11) | 0.0557 (12) | 0.0024 (9) | 0.0156 (9) | 0.0097 (9) |
O3 | 0.0533 (17) | 0.0532 (19) | 0.0413 (16) | −0.0091 (13) | 0.0001 (13) | 0.0031 (13) |
O21 | 0.0474 (16) | 0.0661 (18) | 0.0669 (18) | 0.0059 (13) | 0.0056 (13) | −0.0082 (14) |
C1 | 0.036 (3) | 0.042 (4) | 0.045 (2) | −0.005 (2) | 0.0062 (19) | −0.0026 (19) |
C2 | 0.046 (2) | 0.058 (2) | 0.053 (2) | −0.0114 (18) | 0.0091 (17) | −0.0015 (18) |
C3 | 0.0627 (19) | 0.0551 (18) | 0.0530 (17) | −0.0119 (15) | 0.0071 (14) | 0.0016 (13) |
C16 | 0.037 (2) | 0.061 (3) | 0.055 (3) | −0.0023 (19) | 0.015 (2) | 0.005 (3) |
C17 | 0.054 (3) | 0.042 (3) | 0.050 (3) | −0.007 (2) | 0.006 (3) | −0.002 (2) |
C21 | 0.049 (3) | 0.042 (2) | 0.051 (3) | −0.0122 (19) | 0.008 (2) | 0.0009 (18) |
C22 | 0.060 (3) | 0.060 (5) | 0.041 (3) | −0.008 (3) | 0.004 (2) | −0.001 (2) |
O3B | 0.130 (10) | 0.063 (8) | 0.054 (4) | −0.021 (6) | −0.009 (7) | 0.008 (5) |
O21B | 0.089 (9) | 0.081 (9) | 0.112 (10) | −0.021 (6) | 0.033 (7) | −0.009 (7) |
C1B | 0.038 (8) | 0.018 (8) | 0.047 (4) | −0.002 (6) | 0.021 (6) | −0.006 (5) |
C2B | 0.044 (6) | 0.025 (5) | 0.042 (4) | −0.018 (4) | 0.030 (4) | −0.007 (3) |
C3B | 0.0627 (19) | 0.0551 (18) | 0.0530 (17) | −0.0119 (15) | 0.0071 (14) | 0.0016 (13) |
C16B | 0.041 (8) | 0.047 (9) | 0.027 (8) | 0.007 (6) | 0.014 (7) | 0.003 (7) |
C17B | 0.045 (9) | 0.015 (7) | 0.056 (8) | 0.000 (5) | 0.008 (9) | −0.013 (7) |
C21B | 0.084 (11) | 0.060 (10) | 0.057 (8) | −0.026 (6) | 0.010 (6) | −0.007 (7) |
C22B | 0.11 (3) | 0.060 (19) | 0.085 (19) | −0.04 (2) | 0.037 (17) | −0.026 (12) |
C4 | 0.0424 (15) | 0.0401 (14) | 0.0516 (16) | 0.0070 (12) | 0.0140 (12) | 0.0044 (13) |
C5 | 0.0333 (13) | 0.0339 (13) | 0.0556 (16) | 0.0032 (10) | 0.0142 (12) | −0.0004 (12) |
C6 | 0.0367 (14) | 0.0409 (15) | 0.0518 (16) | −0.0025 (12) | 0.0084 (12) | −0.0026 (12) |
C7 | 0.0372 (15) | 0.0450 (16) | 0.0610 (18) | −0.0069 (12) | 0.0107 (13) | −0.0034 (13) |
C8 | 0.0324 (13) | 0.0391 (14) | 0.0550 (16) | 0.0007 (11) | 0.0055 (11) | −0.0043 (12) |
C9 | 0.0356 (14) | 0.0370 (14) | 0.0604 (18) | 0.0041 (11) | 0.0043 (12) | −0.0065 (12) |
C10 | 0.0340 (14) | 0.0394 (14) | 0.0569 (17) | 0.0034 (11) | 0.0026 (12) | −0.0085 (12) |
C11 | 0.0361 (14) | 0.0372 (14) | 0.0605 (18) | 0.0071 (11) | 0.0001 (12) | −0.0095 (13) |
C12 | 0.0398 (15) | 0.0393 (14) | 0.0574 (17) | 0.0049 (12) | −0.0017 (13) | −0.0095 (13) |
C13 | 0.0395 (15) | 0.0396 (15) | 0.0600 (18) | 0.0091 (12) | −0.0043 (13) | −0.0095 (13) |
C14 | 0.0457 (16) | 0.0396 (15) | 0.0589 (18) | 0.0022 (12) | −0.0056 (13) | −0.0084 (13) |
C15 | 0.0493 (17) | 0.0392 (15) | 0.0606 (18) | 0.0042 (12) | −0.0061 (14) | −0.0091 (13) |
C18 | 0.0458 (16) | 0.0374 (15) | 0.0673 (18) | −0.0012 (12) | 0.0137 (14) | 0.0024 (13) |
C19 | 0.0437 (16) | 0.0528 (17) | 0.0647 (19) | −0.0057 (13) | 0.0042 (14) | −0.0089 (14) |
C20 | 0.0407 (16) | 0.0518 (17) | 0.070 (2) | 0.0043 (13) | −0.0022 (14) | −0.0112 (15) |
O4—C4 | 1.222 (3) | C17B—H17F | 0.9800 |
O3—C21 | 1.342 (5) | C21B—C22B | 1.477 (17) |
O3—C3 | 1.437 (3) | C22B—H22D | 0.9800 |
O21—C21 | 1.192 (4) | C22B—H22E | 0.9800 |
C1—C6 | 1.526 (7) | C22B—H22F | 0.9800 |
C1—C2 | 1.533 (5) | C4—C5 | 1.477 (4) |
C1—C16 | 1.535 (6) | C5—C6 | 1.363 (4) |
C1—C17 | 1.540 (6) | C5—C18 | 1.507 (3) |
C2—C3 | 1.4413 | C6—C7 | 1.455 (4) |
C2—H2A | 0.9900 | C7—C8 | 1.356 (4) |
C2—H2B | 0.9900 | C7—H7 | 0.9500 |
C3—C4 | 1.494 (4) | C8—C9 | 1.450 (4) |
C3—H3 | 1.0000 | C8—H8 | 0.9500 |
C16—H16A | 0.9800 | C9—C10 | 1.357 (4) |
C16—H16B | 0.9800 | C9—C19 | 1.499 (4) |
C16—H16C | 0.9800 | C10—C11 | 1.436 (4) |
C17—H17A | 0.9800 | C10—H10 | 0.9500 |
C17—H17B | 0.9800 | C11—C12 | 1.346 (4) |
C17—H17C | 0.9800 | C11—H11 | 0.9500 |
C21—C22 | 1.493 (8) | C12—C13 | 1.455 (4) |
C22—H22A | 0.9800 | C12—H12 | 0.9500 |
C22—H22B | 0.9800 | C13—C14 | 1.360 (4) |
C22—H22C | 0.9800 | C13—C20 | 1.505 (4) |
O3B—C21B | 1.344 (15) | C14—C15 | 1.436 (4) |
O21B—C21B | 1.208 (15) | C14—H14 | 0.9500 |
C1B—C16B | 1.512 (15) | C15—C15i | 1.347 (6) |
C1B—C2B | 1.523 (15) | C15—H15 | 0.9500 |
C1B—C17B | 1.538 (15) | C18—H18A | 0.9800 |
C1B—C6 | 1.61 (2) | C18—H18B | 0.9800 |
C2B—H2C | 0.9900 | C18—H18C | 0.9800 |
C2B—H2D | 0.9900 | C19—H19A | 0.9800 |
C16B—H16D | 0.9800 | C19—H19B | 0.9800 |
C16B—H16E | 0.9800 | C19—H19C | 0.9800 |
C16B—H16F | 0.9800 | C20—H20A | 0.9800 |
C17B—H17D | 0.9800 | C20—H20B | 0.9800 |
C17B—H17E | 0.9800 | C20—H20C | 0.9800 |
C21—O3—C3 | 117.6 (3) | C6—C5—C4 | 121.7 (2) |
C6—C1—C2 | 111.1 (4) | C6—C5—C18 | 123.7 (2) |
C6—C1—C16 | 113.9 (4) | C4—C5—C18 | 114.6 (2) |
C2—C1—C16 | 103.8 (4) | C5—C6—C7 | 117.3 (2) |
C6—C1—C17 | 107.2 (4) | C5—C6—C1 | 121.8 (3) |
C2—C1—C17 | 110.5 (4) | C7—C6—C1 | 120.7 (3) |
C16—C1—C17 | 110.4 (5) | C5—C6—C1B | 120.7 (6) |
C3—C2—C1 | 115.1 (2) | C7—C6—C1B | 120.0 (6) |
C3—C2—H2A | 108.5 | C1—C6—C1B | 16.6 (6) |
C1—C2—H2A | 108.5 | C8—C7—C6 | 130.8 (3) |
C3—C2—H2B | 108.5 | C8—C7—H7 | 114.6 |
C1—C2—H2B | 108.5 | C6—C7—H7 | 114.6 |
H2A—C2—H2B | 107.5 | C7—C8—C9 | 124.2 (3) |
O3—C3—C2 | 111.02 (15) | C7—C8—H8 | 117.9 |
O3—C3—C4 | 109.6 (2) | C9—C8—H8 | 117.9 |
C2—C3—C4 | 111.57 (14) | C10—C9—C8 | 118.4 (3) |
O3—C3—H3 | 108.2 | C10—C9—C19 | 122.7 (2) |
C2—C3—H3 | 108.2 | C8—C9—C19 | 118.9 (2) |
C4—C3—H3 | 108.2 | C9—C10—C11 | 126.7 (3) |
O21—C21—O3 | 124.9 (4) | C9—C10—H10 | 116.6 |
O21—C21—C22 | 125.9 (5) | C11—C10—H10 | 116.6 |
O3—C21—C22 | 109.2 (5) | C12—C11—C10 | 123.9 (3) |
C16B—C1B—C2B | 108.0 (13) | C12—C11—H11 | 118.0 |
C16B—C1B—C17B | 109.7 (15) | C10—C11—H11 | 118.0 |
C2B—C1B—C17B | 108.4 (13) | C11—C12—C13 | 125.5 (3) |
C16B—C1B—C6 | 102.1 (13) | C11—C12—H12 | 117.2 |
C2B—C1B—C6 | 111.2 (12) | C13—C12—H12 | 117.2 |
C17B—C1B—C6 | 116.9 (15) | C14—C13—C12 | 118.3 (3) |
C1B—C2B—H2C | 107.5 | C14—C13—C20 | 123.1 (2) |
C1B—C2B—H2D | 107.5 | C12—C13—C20 | 118.6 (3) |
H2C—C2B—H2D | 107.0 | C13—C14—C15 | 127.0 (3) |
C1B—C16B—H16D | 109.5 | C13—C14—H14 | 116.5 |
C1B—C16B—H16E | 109.5 | C15—C14—H14 | 116.5 |
H16D—C16B—H16E | 109.5 | C15i—C15—C14 | 123.6 (4) |
C1B—C16B—H16F | 109.5 | C15i—C15—H15 | 118.2 |
H16D—C16B—H16F | 109.5 | C14—C15—H15 | 118.2 |
H16E—C16B—H16F | 109.5 | C5—C18—H18A | 109.5 |
C1B—C17B—H17D | 109.5 | C5—C18—H18B | 109.5 |
C1B—C17B—H17E | 109.5 | H18A—C18—H18B | 109.5 |
H17D—C17B—H17E | 109.5 | C5—C18—H18C | 109.5 |
C1B—C17B—H17F | 109.5 | H18A—C18—H18C | 109.5 |
H17D—C17B—H17F | 109.5 | H18B—C18—H18C | 109.5 |
H17E—C17B—H17F | 109.5 | C9—C19—H19A | 109.5 |
O21B—C21B—O3B | 125.1 (16) | C9—C19—H19B | 109.5 |
O21B—C21B—C22B | 122.5 (19) | H19A—C19—H19B | 109.5 |
O3B—C21B—C22B | 112.2 (19) | C9—C19—H19C | 109.5 |
C21B—C22B—H22D | 109.5 | H19A—C19—H19C | 109.5 |
C21B—C22B—H22E | 109.5 | H19B—C19—H19C | 109.5 |
H22D—C22B—H22E | 109.5 | C13—C20—H20A | 109.5 |
C21B—C22B—H22F | 109.5 | C13—C20—H20B | 109.5 |
H22D—C22B—H22F | 109.5 | H20A—C20—H20B | 109.5 |
H22E—C22B—H22F | 109.5 | C13—C20—H20C | 109.5 |
O4—C4—C5 | 122.6 (2) | H20A—C20—H20C | 109.5 |
O4—C4—C3 | 120.9 (2) | H20B—C20—H20C | 109.5 |
C5—C4—C3 | 116.5 (2) | ||
C6—C1—C2—C3 | −42.2 (4) | C17—C1—C6—C7 | 73.9 (5) |
C16—C1—C2—C3 | −165.0 (3) | C2—C1—C6—C1B | 102 (2) |
C17—C1—C2—C3 | 76.7 (4) | C16—C1—C6—C1B | −141 (2) |
C21—O3—C3—C2 | 150.7 (3) | C17—C1—C6—C1B | −19 (2) |
C21—O3—C3—C4 | −85.6 (3) | C16B—C1B—C6—C5 | 111.8 (9) |
C1—C2—C3—O3 | 178.7 (4) | C2B—C1B—C6—C5 | −3.3 (14) |
C1—C2—C3—C4 | 56.1 (3) | C17B—C1B—C6—C5 | −128.5 (11) |
C3—O3—C21—O21 | −7.8 (6) | C16B—C1B—C6—C7 | −84.3 (11) |
C3—O3—C21—C22 | 171.8 (5) | C2B—C1B—C6—C7 | 160.6 (8) |
O3—C3—C4—O4 | 20.4 (3) | C17B—C1B—C6—C7 | 35.4 (15) |
C2—C3—C4—O4 | 143.8 (2) | C16B—C1B—C6—C1 | 12.9 (16) |
O3—C3—C4—C5 | −161.8 (2) | C2B—C1B—C6—C1 | −102 (3) |
C2—C3—C4—C5 | −38.4 (2) | C17B—C1B—C6—C1 | 133 (3) |
O4—C4—C5—C6 | −173.9 (2) | C5—C6—C7—C8 | 178.3 (3) |
C3—C4—C5—C6 | 8.4 (3) | C1—C6—C7—C8 | −5.4 (5) |
O4—C4—C5—C18 | 6.1 (4) | C1B—C6—C7—C8 | 13.9 (8) |
C3—C4—C5—C18 | −171.7 (2) | C6—C7—C8—C9 | −179.6 (3) |
C4—C5—C6—C7 | −178.7 (2) | C7—C8—C9—C10 | −177.9 (2) |
C18—C5—C6—C7 | 1.4 (4) | C7—C8—C9—C19 | 0.3 (4) |
C4—C5—C6—C1 | 5.1 (4) | C8—C9—C10—C11 | 179.9 (2) |
C18—C5—C6—C1 | −174.8 (3) | C19—C9—C10—C11 | 1.8 (4) |
C4—C5—C6—C1B | −14.4 (8) | C9—C10—C11—C12 | −175.5 (3) |
C18—C5—C6—C1B | 165.7 (8) | C10—C11—C12—C13 | −178.4 (2) |
C2—C1—C6—C5 | 10.9 (5) | C11—C12—C13—C14 | −176.9 (3) |
C16—C1—C6—C5 | 127.6 (4) | C11—C12—C13—C20 | 2.0 (4) |
C17—C1—C6—C5 | −110.0 (4) | C12—C13—C14—C15 | 179.7 (2) |
C2—C1—C6—C7 | −165.2 (3) | C20—C13—C14—C15 | 0.9 (4) |
C16—C1—C6—C7 | −48.5 (5) | C13—C14—C15—C15i | −179.7 (3) |
Symmetry code: (i) −x+1, −y, −z−1. |
C40H50O4 | Z = 1 |
Mr = 594.80 | F(000) = 322 |
Triclinic, P1 | Dx = 1.146 Mg m−3 |
a = 7.7821 (4) Å | Synchrotron radiation, λ = 0.6709 Å |
b = 9.9578 (5) Å | Cell parameters from 4494 reflections |
c = 11.4162 (5) Å | θ = 3.3–30.5° |
α = 88.126 (1)° | µ = 0.07 mm−1 |
β = 78.329 (1)° | T = 100 K |
γ = 84.340 (1)° | Plate, red |
V = 862.08 (7) Å3 | 0.2 × 0.2 × 0.02 mm |
Bruker APEXII CCD area detector diffractometer | 3029 independent reflections |
Radiation source: Station 9.8, SRS, Daresbury | 2910 reflections with I > 2σ(I) |
Silicon monochromator | Rint = 0.016 |
phi and ω scans | θmax = 23.8°, θmin = 2.6° |
Absorption correction: multi-scan SADABS | h = −9→9 |
Tmin = 0.736, Tmax = 1.000 | k = −11→11 |
6688 measured reflections | l = −13→13 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0747P)2 + 0.1591P] where P = (Fo2 + 2Fc2)/3 |
3029 reflections | (Δ/σ)max < 0.001 |
428 parameters | Δρmax = 0.17 e Å−3 |
143 restraints | Δρmin = −0.16 e Å−3 |
C40H50O4 | γ = 84.340 (1)° |
Mr = 594.80 | V = 862.08 (7) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.7821 (4) Å | Synchrotron radiation, λ = 0.6709 Å |
b = 9.9578 (5) Å | µ = 0.07 mm−1 |
c = 11.4162 (5) Å | T = 100 K |
α = 88.126 (1)° | 0.2 × 0.2 × 0.02 mm |
β = 78.329 (1)° |
Bruker APEXII CCD area detector diffractometer | 3029 independent reflections |
Absorption correction: multi-scan SADABS | 2910 reflections with I > 2σ(I) |
Tmin = 0.736, Tmax = 1.000 | Rint = 0.016 |
6688 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 143 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.17 e Å−3 |
3029 reflections | Δρmin = −0.16 e Å−3 |
428 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 | Occ. (<1) | |
O3 | 1.5748 (4) | 1.2999 (3) | 0.0199 (3) | 0.0704 (8) | |
H3 | 1.5429 | 1.3082 | −0.0444 | 0.106* | |
O4 | 1.2814 (3) | 1.2251 (3) | −0.0358 (2) | 0.0555 (6) | |
O3B | −1.1944 (4) | −0.6539 (3) | 1.3235 (2) | 0.0728 (9) | |
H3B | −1.1476 | −0.6619 | 1.3819 | 0.109* | |
O4B | −0.9174 (3) | −0.5515 (3) | 1.3753 (2) | 0.0544 (6) | |
C1 | 1.3989 (4) | 1.0939 (3) | 0.2911 (3) | 0.0415 (7) | |
C2 | 1.4768 (4) | 1.2122 (3) | 0.2166 (3) | 0.0447 (7) | |
H2A | 1.4009 | 1.2943 | 0.2392 | 0.054* | |
H2B | 1.5913 | 1.2235 | 0.2344 | 0.054* | |
C3 | 1.4970 (4) | 1.1919 (3) | 0.0851 (3) | 0.0454 (7) | |
H3A | 1.5740 | 1.1089 | 0.0632 | 0.054* | |
C4 | 1.3186 (4) | 1.1752 (3) | 0.0565 (3) | 0.0419 (7) | |
C5 | 1.1975 (4) | 1.0955 (3) | 0.1406 (3) | 0.0412 (7) | |
C6 | 1.2354 (4) | 1.0563 (3) | 0.2472 (3) | 0.0419 (7) | |
C7 | 1.1177 (9) | 0.9670 (6) | 0.3138 (8) | 0.0359 (13) | 0.638 (17) |
C8 | 1.0287 (4) | 0.8948 (3) | 0.3749 (3) | 0.0420 (7) | 0.638 (17) |
C7A | 1.1492 (16) | 0.9770 (11) | 0.3574 (15) | 0.038 (2) | 0.362 (17) |
H7A | 1.1929 | 0.9914 | 0.4255 | 0.046* | 0.362 (17) |
C8A | 1.0287 (4) | 0.8948 (3) | 0.3749 (3) | 0.0420 (7) | 0.362 (17) |
H8A | 0.9793 | 0.8885 | 0.3078 | 0.050* | 0.362 (17) |
C9 | 0.9513 (4) | 0.8107 (3) | 0.4712 (3) | 0.0384 (6) | |
C10 | 0.8070 (4) | 0.7464 (3) | 0.4648 (3) | 0.0373 (6) | |
H10 | 0.7628 | 0.7582 | 0.3949 | 0.045* | |
C11 | 0.7176 (4) | 0.6622 (3) | 0.5568 (3) | 0.0361 (6) | |
H11 | 0.7605 | 0.6497 | 0.6271 | 0.043* | |
C12 | 0.5747 (4) | 0.5997 (3) | 0.5474 (3) | 0.0360 (6) | |
H12 | 0.5327 | 0.6131 | 0.4768 | 0.043* | |
C13 | 0.4822 (4) | 0.5143 (3) | 0.6376 (2) | 0.0354 (6) | |
C14 | 0.3411 (4) | 0.4553 (3) | 0.6137 (3) | 0.0363 (6) | |
H14 | 0.3102 | 0.4771 | 0.5404 | 0.044* | |
C15 | 0.2367 (4) | 0.3640 (3) | 0.6891 (3) | 0.0359 (6) | |
H15 | 0.2675 | 0.3374 | 0.7615 | 0.043* | |
C15B | 0.0952 (4) | 0.3141 (3) | 0.6604 (2) | 0.0358 (6) | |
H15B | 0.0629 | 0.3425 | 0.5888 | 0.043* | |
C14B | −0.0076 (4) | 0.2199 (3) | 0.7344 (2) | 0.0346 (6) | |
H14B | 0.0236 | 0.1969 | 0.8074 | 0.042* | |
C13B | −0.1448 (4) | 0.1612 (3) | 0.7094 (2) | 0.0351 (6) | |
C12B | −0.2361 (4) | 0.0702 (3) | 0.7966 (2) | 0.0350 (6) | |
H12B | −0.1930 | 0.0540 | 0.8665 | 0.042* | |
C11B | −0.3776 (4) | 0.0068 (3) | 0.7864 (3) | 0.0363 (6) | |
H11B | −0.4200 | 0.0199 | 0.7159 | 0.044* | |
C10B | −0.4665 (4) | −0.0790 (3) | 0.8764 (3) | 0.0355 (6) | |
H10B | −0.4197 | −0.0926 | 0.9450 | 0.043* | |
C9B | −0.6104 (4) | −0.1426 (3) | 0.8733 (3) | 0.0378 (6) | |
C7B | −0.8129 (8) | −0.3041 (6) | 0.9895 (7) | 0.0343 (13) | 0.638 (17) |
H7B | −0.8560 | −0.3150 | 0.9205 | 0.041* | 0.638 (17) |
C8B | −0.6865 (4) | −0.2235 (3) | 0.9741 (3) | 0.0432 (7) | 0.638 (17) |
H8B | −0.6363 | −0.2173 | 1.0409 | 0.052* | 0.638 (17) |
C7BB | −0.7805 (14) | −0.2885 (10) | 1.0321 (13) | 0.035 (2) | 0.362 (17) |
C8BB | −0.6865 (4) | −0.2235 (3) | 0.9741 (3) | 0.0432 (7) | 0.362 (17) |
C6B | −0.9018 (4) | −0.3816 (3) | 1.0934 (3) | 0.0428 (7) | |
C5B | −0.8453 (4) | −0.4276 (3) | 1.1941 (3) | 0.0441 (8) | |
C4B | −0.9459 (4) | −0.5222 (3) | 1.2762 (3) | 0.0408 (7) | |
C3B | −1.0860 (4) | −0.5869 (3) | 1.2301 (3) | 0.0450 (7) | |
H3B1 | −1.0274 | −0.6539 | 1.1705 | 0.054* | |
C2B | −1.1888 (4) | −0.4821 (3) | 1.1699 (3) | 0.0413 (6) | |
H2B1 | −1.2436 | −0.4130 | 1.2270 | 0.050* | |
H2B2 | −1.2818 | −0.5230 | 1.1429 | 0.050* | |
C1B | −1.0741 (4) | −0.4169 (3) | 1.0632 (3) | 0.0412 (7) | |
C16 | 1.5320 (5) | 0.9694 (4) | 0.2824 (4) | 0.0579 (8) | |
H16A | 1.5594 | 0.9375 | 0.2017 | 0.087* | |
H16B | 1.4826 | 0.8999 | 0.3352 | 0.087* | |
H16C | 1.6376 | 0.9927 | 0.3049 | 0.087* | |
C17 | 1.3463 (7) | 1.1412 (5) | 0.4208 (3) | 0.0804 (13) | |
H17A | 1.3042 | 1.0678 | 0.4717 | 0.121* | 0.638 (17) |
H17B | 1.2549 | 1.2143 | 0.4268 | 0.121* | 0.638 (17) |
H17C | 1.4469 | 1.1713 | 0.4454 | 0.121* | 0.638 (17) |
H17D | 1.3665 | 1.2345 | 0.4242 | 0.121* | 0.362 (17) |
H17E | 1.4158 | 1.0880 | 0.4691 | 0.121* | 0.362 (17) |
H17F | 1.2237 | 1.1309 | 0.4505 | 0.121* | 0.362 (17) |
C18 | 1.0340 (5) | 1.0653 (3) | 0.0977 (4) | 0.0604 (10) | |
H18A | 1.0669 | 1.0070 | 0.0299 | 0.091* | |
H18B | 0.9740 | 1.1481 | 0.0751 | 0.091* | |
H18C | 0.9572 | 1.0217 | 0.1608 | 0.091* | |
C19 | 1.0397 (5) | 0.7987 (4) | 0.5771 (3) | 0.0565 (9) | |
H19A | 1.0045 | 0.7208 | 0.6243 | 0.085* | |
H19B | 1.0059 | 0.8781 | 0.6249 | 0.085* | |
H19C | 1.1653 | 0.7895 | 0.5497 | 0.085* | |
C20 | 0.5435 (4) | 0.4920 (3) | 0.7534 (3) | 0.0413 (7) | |
H20A | 0.4591 | 0.4452 | 0.8088 | 0.062* | |
H20B | 0.5552 | 0.5775 | 0.7861 | 0.062* | |
H20C | 0.6555 | 0.4391 | 0.7398 | 0.062* | |
C16B | −1.1812 (5) | −0.2881 (4) | 1.0300 (3) | 0.0575 (8) | |
H16D | −1.2922 | −0.3106 | 1.0157 | 0.086* | |
H16E | −1.1167 | −0.2478 | 0.9591 | 0.086* | |
H16F | −1.2014 | −0.2254 | 1.0946 | 0.086* | |
C17B | −1.0380 (6) | −0.5118 (4) | 0.9546 (3) | 0.0620 (9) | |
H17H | −0.9745 | −0.5946 | 0.9736 | 0.093* | |
H17I | −0.9693 | −0.4690 | 0.8869 | 0.093* | |
H17J | −1.1479 | −0.5309 | 0.9359 | 0.093* | |
C18B | −0.6797 (4) | −0.3914 (4) | 1.2281 (4) | 0.0625 (11) | |
H18D | −0.5816 | −0.4119 | 1.1634 | 0.094* | |
H18E | −0.6609 | −0.4423 | 1.2980 | 0.094* | |
H18F | −0.6906 | −0.2967 | 1.2448 | 0.094* | |
C19B | −0.6997 (5) | −0.1330 (4) | 0.7684 (3) | 0.0557 (9) | |
H19D | −0.6286 | −0.0885 | 0.7028 | 0.084* | |
H19E | −0.8127 | −0.0824 | 0.7900 | 0.084* | |
H19F | −0.7151 | −0.2221 | 0.7450 | 0.084* | |
C20B | −0.2094 (4) | 0.1849 (3) | 0.5930 (3) | 0.0462 (8) | |
H20D | −0.1342 | 0.2422 | 0.5412 | 0.069* | |
H20E | −0.3278 | 0.2276 | 0.6093 | 0.069* | |
H20F | −0.2073 | 0.1001 | 0.5549 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0710 (17) | 0.0839 (18) | 0.0601 (16) | −0.0437 (14) | −0.0091 (13) | 0.0292 (14) |
O4 | 0.0581 (14) | 0.0604 (14) | 0.0492 (13) | −0.0059 (11) | −0.0149 (11) | 0.0102 (11) |
O3B | 0.0741 (18) | 0.099 (2) | 0.0596 (16) | −0.0606 (16) | −0.0275 (13) | 0.0407 (15) |
O4B | 0.0535 (13) | 0.0651 (15) | 0.0492 (13) | −0.0147 (11) | −0.0183 (10) | 0.0070 (11) |
C1 | 0.0471 (16) | 0.0424 (15) | 0.0322 (14) | −0.0059 (12) | −0.0010 (12) | 0.0007 (12) |
C2 | 0.0478 (16) | 0.0425 (16) | 0.0462 (16) | −0.0158 (13) | −0.0095 (13) | −0.0004 (12) |
C3 | 0.0447 (15) | 0.0520 (17) | 0.0396 (15) | −0.0206 (13) | −0.0025 (12) | 0.0058 (12) |
C4 | 0.0444 (15) | 0.0362 (15) | 0.0436 (16) | −0.0049 (12) | −0.0045 (13) | −0.0023 (12) |
C5 | 0.0370 (15) | 0.0304 (14) | 0.0549 (19) | −0.0080 (11) | −0.0033 (13) | −0.0031 (13) |
C6 | 0.0360 (15) | 0.0294 (13) | 0.0528 (18) | −0.0056 (11) | 0.0103 (12) | 0.0000 (12) |
C7 | 0.035 (2) | 0.034 (2) | 0.038 (3) | −0.0076 (17) | −0.004 (2) | −0.004 (2) |
C8 | 0.0362 (13) | 0.0377 (14) | 0.0498 (17) | −0.0118 (11) | 0.0019 (12) | −0.0036 (12) |
C7A | 0.036 (4) | 0.039 (3) | 0.038 (4) | −0.012 (3) | −0.001 (3) | 0.000 (3) |
C8A | 0.0362 (13) | 0.0377 (14) | 0.0498 (17) | −0.0118 (11) | 0.0019 (12) | −0.0036 (12) |
C9 | 0.0364 (14) | 0.0385 (15) | 0.0405 (16) | −0.0107 (11) | −0.0045 (11) | −0.0005 (12) |
C10 | 0.0406 (15) | 0.0383 (15) | 0.0346 (14) | −0.0098 (12) | −0.0094 (12) | 0.0042 (12) |
C11 | 0.0375 (14) | 0.0362 (14) | 0.0353 (14) | −0.0086 (12) | −0.0069 (11) | 0.0036 (11) |
C12 | 0.0381 (14) | 0.0396 (15) | 0.0319 (14) | −0.0093 (12) | −0.0084 (11) | 0.0031 (11) |
C13 | 0.0378 (15) | 0.0354 (14) | 0.0325 (14) | −0.0094 (11) | −0.0034 (11) | 0.0015 (11) |
C14 | 0.0373 (14) | 0.0415 (14) | 0.0310 (14) | −0.0120 (12) | −0.0060 (11) | 0.0036 (11) |
C15 | 0.0393 (15) | 0.0385 (15) | 0.0281 (13) | −0.0093 (12) | 0.0003 (11) | 0.0003 (11) |
C15B | 0.0393 (15) | 0.0412 (15) | 0.0254 (13) | −0.0098 (12) | 0.0005 (11) | −0.0002 (11) |
C14B | 0.0415 (14) | 0.0357 (14) | 0.0245 (12) | −0.0095 (11) | 0.0010 (10) | 0.0006 (10) |
C13B | 0.0378 (14) | 0.0373 (14) | 0.0285 (14) | −0.0068 (12) | −0.0014 (11) | 0.0000 (11) |
C12B | 0.0367 (14) | 0.0381 (14) | 0.0298 (14) | −0.0091 (11) | −0.0037 (11) | 0.0043 (11) |
C11B | 0.0382 (14) | 0.0391 (15) | 0.0323 (14) | −0.0068 (12) | −0.0082 (11) | 0.0019 (11) |
C10B | 0.0354 (14) | 0.0362 (14) | 0.0360 (14) | −0.0074 (11) | −0.0091 (11) | 0.0051 (11) |
C9B | 0.0353 (14) | 0.0399 (15) | 0.0386 (15) | −0.0080 (11) | −0.0060 (11) | −0.0029 (11) |
C7B | 0.031 (2) | 0.033 (2) | 0.041 (3) | −0.0079 (16) | −0.008 (2) | −0.004 (2) |
C8B | 0.0364 (14) | 0.0366 (14) | 0.0535 (17) | −0.0098 (11) | 0.0020 (12) | −0.0060 (12) |
C7BB | 0.030 (3) | 0.035 (3) | 0.042 (4) | −0.016 (3) | −0.006 (3) | −0.013 (3) |
C8BB | 0.0364 (14) | 0.0366 (14) | 0.0535 (17) | −0.0098 (11) | 0.0020 (12) | −0.0060 (12) |
C6B | 0.0335 (14) | 0.0310 (14) | 0.0568 (18) | −0.0031 (11) | 0.0077 (12) | 0.0018 (12) |
C5B | 0.0319 (14) | 0.0308 (14) | 0.066 (2) | −0.0053 (11) | −0.0007 (14) | 0.0009 (14) |
C4B | 0.0361 (14) | 0.0395 (15) | 0.0472 (17) | −0.0084 (11) | −0.0069 (12) | 0.0005 (12) |
C3B | 0.0470 (16) | 0.0497 (17) | 0.0406 (15) | −0.0243 (13) | −0.0061 (12) | 0.0090 (13) |
C2B | 0.0388 (14) | 0.0498 (16) | 0.0366 (14) | −0.0162 (12) | −0.0045 (11) | −0.0030 (11) |
C1B | 0.0448 (16) | 0.0401 (16) | 0.0348 (15) | −0.0019 (13) | −0.0004 (12) | 0.0038 (12) |
C16 | 0.0499 (18) | 0.0511 (18) | 0.070 (2) | −0.0031 (14) | −0.0077 (15) | 0.0075 (15) |
C17 | 0.108 (3) | 0.085 (3) | 0.0380 (19) | 0.010 (2) | 0.0008 (19) | −0.0062 (18) |
C18 | 0.0474 (18) | 0.0379 (17) | 0.100 (3) | −0.0126 (14) | −0.0202 (19) | 0.0035 (18) |
C19 | 0.0477 (18) | 0.076 (2) | 0.0519 (19) | −0.0278 (17) | −0.0158 (15) | 0.0071 (17) |
C20 | 0.0475 (16) | 0.0460 (16) | 0.0332 (15) | −0.0195 (13) | −0.0084 (13) | 0.0069 (12) |
C16B | 0.0566 (19) | 0.0510 (19) | 0.059 (2) | 0.0059 (15) | −0.0048 (15) | 0.0053 (15) |
C17B | 0.087 (3) | 0.0543 (19) | 0.0382 (17) | 0.0064 (17) | −0.0023 (16) | −0.0032 (14) |
C18B | 0.0365 (16) | 0.0468 (18) | 0.107 (3) | −0.0140 (14) | −0.0201 (19) | 0.0218 (19) |
C19B | 0.0489 (18) | 0.077 (2) | 0.0459 (18) | −0.0251 (17) | −0.0104 (15) | −0.0022 (17) |
C20B | 0.0503 (18) | 0.0558 (19) | 0.0350 (16) | −0.0208 (14) | −0.0082 (13) | 0.0087 (14) |
O3—C3 | 1.404 (4) | C7B—C8B | 1.312 (8) |
O3—H3 | 0.8200 | C7B—C6B | 1.481 (6) |
O4—C4 | 1.225 (4) | C7B—H7B | 0.9300 |
O3B—C3B | 1.413 (3) | C8B—H8B | 0.9300 |
O3B—H3B | 0.8200 | C7BB—C6B | 1.450 (9) |
O4B—C4B | 1.217 (4) | C6B—C5B | 1.362 (5) |
C1—C16 | 1.527 (5) | C6B—C1B | 1.525 (5) |
C1—C17 | 1.532 (5) | C5B—C4B | 1.473 (4) |
C1—C2 | 1.532 (4) | C5B—C18B | 1.498 (5) |
C1—C6 | 1.541 (5) | C4B—C3B | 1.508 (4) |
C2—C3 | 1.496 (4) | C3B—C2B | 1.487 (4) |
C2—H2A | 0.9700 | C3B—H3B1 | 0.9800 |
C2—H2B | 0.9700 | C2B—C1B | 1.525 (4) |
C3—C4 | 1.515 (4) | C2B—H2B1 | 0.9700 |
C3—H3A | 0.9800 | C2B—H2B2 | 0.9700 |
C4—C5 | 1.473 (4) | C1B—C16B | 1.539 (4) |
C5—C6 | 1.347 (5) | C1B—C17B | 1.547 (4) |
C5—C18 | 1.512 (5) | C16—H16A | 0.9600 |
C6—C7 | 1.429 (6) | C16—H16B | 0.9600 |
C6—C7A | 1.535 (12) | C16—H16C | 0.9600 |
C7—C8 | 1.163 (6) | C17—H17A | 0.9600 |
C8—C9 | 1.430 (4) | C17—H17B | 0.9600 |
C7A—H7A | 0.9300 | C17—H17C | 0.9600 |
C9—C10 | 1.362 (4) | C17—H17D | 0.9600 |
C9—C19 | 1.504 (5) | C17—H17E | 0.9600 |
C10—C11 | 1.433 (4) | C17—H17F | 0.9600 |
C10—H10 | 0.9300 | C18—H18A | 0.9600 |
C11—C12 | 1.350 (4) | C18—H18B | 0.9600 |
C11—H11 | 0.9300 | C18—H18C | 0.9600 |
C12—C13 | 1.437 (4) | C19—H19A | 0.9600 |
C12—H12 | 0.9300 | C19—H19B | 0.9600 |
C13—C14 | 1.373 (4) | C19—H19C | 0.9600 |
C13—C20 | 1.497 (4) | C20—H20A | 0.9600 |
C14—C15 | 1.428 (4) | C20—H20B | 0.9600 |
C14—H14 | 0.9300 | C20—H20C | 0.9600 |
C15—C15B | 1.353 (3) | C16B—H16D | 0.9600 |
C15—H15 | 0.9300 | C16B—H16E | 0.9600 |
C15B—C14B | 1.434 (4) | C16B—H16F | 0.9600 |
C15B—H15B | 0.9300 | C17B—H17H | 0.9600 |
C14B—C13B | 1.350 (4) | C17B—H17I | 0.9600 |
C14B—H14B | 0.9300 | C17B—H17J | 0.9600 |
C13B—C12B | 1.448 (4) | C18B—H18D | 0.9600 |
C13B—C20B | 1.516 (4) | C18B—H18E | 0.9600 |
C12B—C11B | 1.348 (4) | C18B—H18F | 0.9600 |
C12B—H12B | 0.9300 | C19B—H19D | 0.9600 |
C11B—C10B | 1.427 (4) | C19B—H19E | 0.9600 |
C11B—H11B | 0.9300 | C19B—H19F | 0.9600 |
C10B—C9B | 1.346 (4) | C20B—H20D | 0.9600 |
C10B—H10B | 0.9300 | C20B—H20E | 0.9600 |
C9B—C8B | 1.443 (4) | C20B—H20F | 0.9600 |
C9B—C19B | 1.498 (5) | ||
C3—O3—H3 | 109.5 | C5B—C4B—C3B | 116.5 (3) |
C3B—O3B—H3B | 109.5 | O3B—C3B—C2B | 112.2 (3) |
C16—C1—C17 | 110.0 (3) | O3B—C3B—C4B | 110.8 (2) |
C16—C1—C2 | 111.6 (3) | C2B—C3B—C4B | 109.1 (2) |
C17—C1—C2 | 106.7 (3) | O3B—C3B—H3B1 | 108.2 |
C16—C1—C6 | 108.5 (3) | C2B—C3B—H3B1 | 108.2 |
C17—C1—C6 | 110.0 (3) | C4B—C3B—H3B1 | 108.2 |
C2—C1—C6 | 110.0 (2) | C3B—C2B—C1B | 112.2 (2) |
C3—C2—C1 | 112.5 (2) | C3B—C2B—H2B1 | 109.2 |
C3—C2—H2A | 109.1 | C1B—C2B—H2B1 | 109.2 |
C1—C2—H2A | 109.1 | C3B—C2B—H2B2 | 109.2 |
C3—C2—H2B | 109.1 | C1B—C2B—H2B2 | 109.2 |
C1—C2—H2B | 109.1 | H2B1—C2B—H2B2 | 107.9 |
H2A—C2—H2B | 107.8 | C2B—C1B—C6B | 111.4 (2) |
O3—C3—C2 | 110.8 (2) | C2B—C1B—C16B | 107.1 (2) |
O3—C3—C4 | 111.3 (3) | C6B—C1B—C16B | 110.1 (3) |
C2—C3—C4 | 109.4 (2) | C2B—C1B—C17B | 109.8 (3) |
O3—C3—H3A | 108.4 | C6B—C1B—C17B | 110.8 (3) |
C2—C3—H3A | 108.4 | C16B—C1B—C17B | 107.5 (3) |
C4—C3—H3A | 108.4 | C1—C16—H16A | 109.5 |
O4—C4—C5 | 122.5 (3) | C1—C16—H16B | 109.5 |
O4—C4—C3 | 119.5 (3) | H16A—C16—H16B | 109.5 |
C5—C4—C3 | 118.0 (3) | C1—C16—H16C | 109.5 |
C6—C5—C4 | 120.1 (3) | H16A—C16—H16C | 109.5 |
C6—C5—C18 | 124.8 (3) | H16B—C16—H16C | 109.5 |
C4—C5—C18 | 115.1 (3) | C1—C17—H17A | 109.5 |
C5—C6—C7 | 114.1 (5) | C1—C17—H17B | 109.5 |
C5—C6—C1 | 123.7 (3) | H17A—C17—H17B | 109.5 |
C7—C6—C1 | 121.9 (5) | C1—C17—H17C | 109.5 |
C5—C6—C7A | 136.8 (7) | H17A—C17—H17C | 109.5 |
C7—C6—C7A | 23.5 (4) | H17B—C17—H17C | 109.5 |
C1—C6—C7A | 99.4 (7) | C1—C17—H17D | 109.5 |
C8—C7—C6 | 174.9 (9) | H17A—C17—H17D | 141.1 |
C7—C8—C9 | 164.4 (6) | H17B—C17—H17D | 56.3 |
C6—C7A—H7A | 113.4 | H17C—C17—H17D | 56.3 |
C10—C9—C8 | 120.9 (3) | C1—C17—H17E | 109.5 |
C10—C9—C19 | 123.3 (3) | H17A—C17—H17E | 56.3 |
C8—C9—C19 | 115.7 (3) | H17B—C17—H17E | 141.1 |
C9—C10—C11 | 125.4 (3) | H17C—C17—H17E | 56.3 |
C9—C10—H10 | 117.3 | H17D—C17—H17E | 109.5 |
C11—C10—H10 | 117.3 | C1—C17—H17F | 109.5 |
C12—C11—C10 | 123.9 (3) | H17A—C17—H17F | 56.3 |
C12—C11—H11 | 118.1 | H17B—C17—H17F | 56.3 |
C10—C11—H11 | 118.1 | H17C—C17—H17F | 141.1 |
C11—C12—C13 | 125.3 (3) | H17D—C17—H17F | 109.5 |
C11—C12—H12 | 117.3 | H17E—C17—H17F | 109.5 |
C13—C12—H12 | 117.3 | C5—C18—H18A | 109.5 |
C14—C13—C12 | 118.5 (3) | C5—C18—H18B | 109.5 |
C14—C13—C20 | 122.4 (3) | H18A—C18—H18B | 109.5 |
C12—C13—C20 | 119.1 (2) | C5—C18—H18C | 109.5 |
C13—C14—C15 | 127.1 (3) | H18A—C18—H18C | 109.5 |
C13—C14—H14 | 116.4 | H18B—C18—H18C | 109.5 |
C15—C14—H14 | 116.4 | C9—C19—H19A | 109.5 |
C15B—C15—C14 | 123.3 (2) | C9—C19—H19B | 109.5 |
C15B—C15—H15 | 118.4 | H19A—C19—H19B | 109.5 |
C14—C15—H15 | 118.4 | C9—C19—H19C | 109.5 |
C15—C15B—C14B | 123.5 (2) | H19A—C19—H19C | 109.5 |
C15—C15B—H15B | 118.2 | H19B—C19—H19C | 109.5 |
C14B—C15B—H15B | 118.2 | C13—C20—H20A | 109.5 |
C13B—C14B—C15B | 126.9 (3) | C13—C20—H20B | 109.5 |
C13B—C14B—H14B | 116.5 | H20A—C20—H20B | 109.5 |
C15B—C14B—H14B | 116.5 | C13—C20—H20C | 109.5 |
C14B—C13B—C12B | 119.3 (3) | H20A—C20—H20C | 109.5 |
C14B—C13B—C20B | 123.2 (3) | H20B—C20—H20C | 109.5 |
C12B—C13B—C20B | 117.5 (2) | C1B—C16B—H16D | 109.5 |
C11B—C12B—C13B | 126.4 (3) | C1B—C16B—H16E | 109.5 |
C11B—C12B—H12B | 116.8 | H16D—C16B—H16E | 109.5 |
C13B—C12B—H12B | 116.8 | C1B—C16B—H16F | 109.5 |
C12B—C11B—C10B | 124.4 (3) | H16D—C16B—H16F | 109.5 |
C12B—C11B—H11B | 117.8 | H16E—C16B—H16F | 109.5 |
C10B—C11B—H11B | 117.8 | C1B—C17B—H17H | 109.5 |
C9B—C10B—C11B | 127.5 (3) | C1B—C17B—H17I | 109.5 |
C9B—C10B—H10B | 116.3 | H17H—C17B—H17I | 109.5 |
C11B—C10B—H10B | 116.3 | C1B—C17B—H17J | 109.5 |
C10B—C9B—C8B | 120.3 (3) | H17H—C17B—H17J | 109.5 |
C10B—C9B—C19B | 122.9 (3) | H17I—C17B—H17J | 109.5 |
C8B—C9B—C19B | 116.9 (3) | C5B—C18B—H18D | 109.5 |
C8B—C7B—C6B | 133.7 (8) | C5B—C18B—H18E | 109.5 |
C8B—C7B—H7B | 113.1 | H18D—C18B—H18E | 109.5 |
C6B—C7B—H7B | 113.1 | C5B—C18B—H18F | 109.5 |
C7B—C8B—C9B | 132.2 (5) | H18D—C18B—H18F | 109.5 |
C7B—C8B—H8B | 113.9 | H18E—C18B—H18F | 109.5 |
C9B—C8B—H8B | 113.9 | C9B—C19B—H19D | 109.5 |
C5B—C6B—C7BB | 108.1 (7) | C9B—C19B—H19E | 109.5 |
C5B—C6B—C7B | 130.4 (4) | H19D—C19B—H19E | 109.5 |
C7BB—C6B—C7B | 24.5 (4) | C9B—C19B—H19F | 109.5 |
C5B—C6B—C1B | 123.0 (3) | H19D—C19B—H19F | 109.5 |
C7BB—C6B—C1B | 128.7 (7) | H19E—C19B—H19F | 109.5 |
C7B—C6B—C1B | 106.4 (4) | C13B—C20B—H20D | 109.5 |
C6B—C5B—C4B | 120.3 (3) | C13B—C20B—H20E | 109.5 |
C6B—C5B—C18B | 124.2 (3) | H20D—C20B—H20E | 109.5 |
C4B—C5B—C18B | 115.5 (3) | C13B—C20B—H20F | 109.5 |
O4B—C4B—C5B | 123.3 (3) | H20D—C20B—H20F | 109.5 |
O4B—C4B—C3B | 120.2 (3) | H20E—C20B—H20F | 109.5 |
C16—C1—C2—C3 | 72.6 (4) | C15—C15B—C14B—C13B | −176.7 (3) |
C17—C1—C2—C3 | −167.2 (3) | C15B—C14B—C13B—C12B | −178.6 (2) |
C6—C1—C2—C3 | −47.9 (3) | C15B—C14B—C13B—C20B | 1.6 (5) |
C1—C2—C3—O3 | −177.7 (3) | C14B—C13B—C12B—C11B | 178.1 (3) |
C1—C2—C3—C4 | 59.2 (3) | C20B—C13B—C12B—C11B | −2.1 (4) |
O3—C3—C4—O4 | 19.3 (4) | C13B—C12B—C11B—C10B | −178.1 (3) |
C2—C3—C4—O4 | 142.1 (3) | C12B—C11B—C10B—C9B | 178.2 (3) |
O3—C3—C4—C5 | −162.3 (3) | C11B—C10B—C9B—C8B | −178.4 (3) |
C2—C3—C4—C5 | −39.5 (4) | C11B—C10B—C9B—C19B | 1.1 (5) |
O4—C4—C5—C6 | −172.2 (3) | C6B—C7B—C8B—C9B | −175.4 (4) |
C3—C4—C5—C6 | 9.5 (4) | C10B—C9B—C8B—C7B | −172.6 (4) |
O4—C4—C5—C18 | 7.1 (4) | C19B—C9B—C8B—C7B | 7.8 (6) |
C3—C4—C5—C18 | −171.2 (3) | C8B—C7B—C6B—C5B | −23.8 (9) |
C4—C5—C6—C7 | −173.2 (3) | C8B—C7B—C6B—C7BB | 3.7 (10) |
C18—C5—C6—C7 | 7.5 (5) | C8B—C7B—C6B—C1B | 161.8 (5) |
C4—C5—C6—C1 | 2.1 (4) | C7BB—C6B—C5B—C4B | 178.6 (5) |
C18—C5—C6—C1 | −177.1 (3) | C7B—C6B—C5B—C4B | −169.8 (4) |
C4—C5—C6—C7A | 179.2 (7) | C1B—C6B—C5B—C4B | 3.7 (4) |
C18—C5—C6—C7A | −0.1 (9) | C7BB—C6B—C5B—C18B | −3.1 (6) |
C16—C1—C6—C5 | −105.4 (3) | C7B—C6B—C5B—C18B | 8.5 (6) |
C17—C1—C6—C5 | 134.2 (3) | C1B—C6B—C5B—C18B | −178.0 (3) |
C2—C1—C6—C5 | 16.9 (4) | C6B—C5B—C4B—O4B | −168.9 (3) |
C16—C1—C6—C7 | 69.5 (4) | C18B—C5B—C4B—O4B | 12.7 (5) |
C17—C1—C6—C7 | −50.8 (5) | C6B—C5B—C4B—C3B | 13.0 (4) |
C2—C1—C6—C7 | −168.1 (4) | C18B—C5B—C4B—C3B | −165.4 (3) |
C16—C1—C6—C7A | 76.6 (5) | O4B—C4B—C3B—O3B | 13.2 (4) |
C17—C1—C6—C7A | −43.8 (6) | C5B—C4B—C3B—O3B | −168.7 (3) |
C2—C1—C6—C7A | −161.1 (5) | O4B—C4B—C3B—C2B | 137.2 (3) |
C5—C6—C7—C8 | −176 (6) | C5B—C4B—C3B—C2B | −44.7 (3) |
C1—C6—C7—C8 | 9 (7) | O3B—C3B—C2B—C1B | −175.8 (3) |
C7A—C6—C7—C8 | −9 (5) | C4B—C3B—C2B—C1B | 61.0 (3) |
C6—C7—C8—C9 | −3 (8) | C3B—C2B—C1B—C6B | −44.9 (3) |
C7—C8—C9—C10 | 179.8 (14) | C3B—C2B—C1B—C16B | −165.3 (3) |
C7—C8—C9—C19 | −0.4 (17) | C3B—C2B—C1B—C17B | 78.2 (3) |
C8—C9—C10—C11 | −178.8 (3) | C5B—C6B—C1B—C2B | 12.1 (4) |
C19—C9—C10—C11 | 1.4 (5) | C7BB—C6B—C1B—C2B | −161.6 (6) |
C9—C10—C11—C12 | −179.9 (3) | C7B—C6B—C1B—C2B | −173.0 (3) |
C10—C11—C12—C13 | 179.8 (3) | C5B—C6B—C1B—C16B | 130.7 (3) |
C11—C12—C13—C14 | −178.5 (3) | C7BB—C6B—C1B—C16B | −43.0 (7) |
C11—C12—C13—C20 | 1.1 (5) | C7B—C6B—C1B—C16B | −54.4 (4) |
C12—C13—C14—C15 | 177.6 (3) | C5B—C6B—C1B—C17B | −110.4 (3) |
C20—C13—C14—C15 | −2.0 (5) | C7BB—C6B—C1B—C17B | 75.8 (6) |
C13—C14—C15—C15B | 177.4 (3) | C7B—C6B—C1B—C17B | 64.5 (4) |
C14—C15—C15B—C14B | 178.5 (3) |
C40H48O4 | Z = 1 |
Mr = 592.78 | F(000) = 320 |
Triclinic, P1 | Dx = 1.148 Mg m−3 |
Hall symbol: P1 | Synchrotron radiation, λ = 0.67100 Å |
a = 7.4769 (14) Å | Cell parameters from 979 reflections |
b = 10.4729 (19) Å | θ = 2.3–24.0° |
c = 11.633 (2) Å | µ = 0.07 mm−1 |
α = 75.606 (2)° | T = 100 K |
β = 85.901 (2)° | Plate, red |
γ = 76.389 (2)° | 0.04 × 0.03 × 0.01 mm |
V = 857.5 (3) Å3 |
Bruker APEXII CCD area detector diffractometer | 4002 independent reflections |
Radiation source: Station 9.8, SRS, Daresbury | 2799 reflections with I > 2σ(I) |
Silicon monochromator | Rint = 0.062 |
phi and ω scans | θmax = 26.1°, θmin = 2.0° |
Absorption correction: multi-scan SADABS | h = −9→9 |
Tmin = 0.749, Tmax = 1.000 | k = −13→13 |
14633 measured reflections | l = −15→15 |
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) = 0.105 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0581P)2] where P = (Fo2 + 2Fc2)/3 |
4002 reflections | (Δ/σ)max = 0.003 |
409 parameters | Δρmax = 0.19 e Å−3 |
3 restraints | Δρmin = −0.17 e Å−3 |
C40H48O4 | γ = 76.389 (2)° |
Mr = 592.78 | V = 857.5 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.4769 (14) Å | Synchrotron radiation, λ = 0.67100 Å |
b = 10.4729 (19) Å | µ = 0.07 mm−1 |
c = 11.633 (2) Å | T = 100 K |
α = 75.606 (2)° | 0.04 × 0.03 × 0.01 mm |
β = 85.901 (2)° |
Bruker APEXII CCD area detector diffractometer | 4002 independent reflections |
Absorption correction: multi-scan SADABS | 2799 reflections with I > 2σ(I) |
Tmin = 0.749, Tmax = 1.000 | Rint = 0.062 |
14633 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 3 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.19 e Å−3 |
4002 reflections | Δρmin = −0.17 e Å−3 |
409 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 | ||
O3 | 0.8989 (3) | 1.2181 (2) | 1.2004 (2) | 0.0432 (5) | |
H3 | 0.9492 | 1.1765 | 1.2634 | 0.065* | |
O4 | 1.0608 (3) | 0.9612 (2) | 1.28650 (17) | 0.0343 (5) | |
O3B | 0.5316 (3) | −0.08464 (19) | −0.76918 (19) | 0.0396 (5) | |
H3B | 0.4859 | −0.0538 | −0.8351 | 0.059* | |
O4B | 0.3773 (3) | 0.1658 (2) | −0.87573 (17) | 0.0367 (5) | |
C1 | 0.9374 (4) | 1.0816 (3) | 0.9257 (3) | 0.0287 (6) | |
C2 | 0.9550 (4) | 1.1761 (3) | 1.0039 (3) | 0.0312 (6) | |
H2A | 1.0821 | 1.1833 | 1.0030 | 0.037* | |
H2B | 0.8805 | 1.2657 | 0.9714 | 0.037* | |
C3 | 0.8949 (4) | 1.1264 (3) | 1.1297 (2) | 0.0314 (6) | |
H3A | 0.7682 | 1.1157 | 1.1291 | 0.038* | |
C4 | 1.0166 (4) | 0.9893 (3) | 1.1820 (2) | 0.0271 (6) | |
C5 | 1.0676 (4) | 0.8941 (3) | 1.1061 (2) | 0.0257 (6) | |
C6 | 1.0188 (4) | 0.9345 (3) | 0.9905 (2) | 0.0249 (6) | |
C7 | 1.0400 (4) | 0.8359 (3) | 0.9220 (2) | 0.0283 (6) | |
C8 | 1.0452 (4) | 0.7499 (3) | 0.8686 (2) | 0.0273 (6) | |
C9 | 1.0483 (4) | 0.6431 (3) | 0.8133 (2) | 0.0267 (6) | |
C10 | 0.9954 (4) | 0.6728 (3) | 0.6992 (2) | 0.0261 (6) | |
H10 | 0.9680 | 0.7641 | 0.6604 | 0.031* | |
C11 | 0.9766 (4) | 0.5803 (3) | 0.6308 (2) | 0.0273 (7) | |
H11 | 1.0066 | 0.4880 | 0.6656 | 0.033* | |
C12 | 0.9172 (4) | 0.6216 (3) | 0.5181 (2) | 0.0266 (6) | |
H12 | 0.8927 | 0.7144 | 0.4855 | 0.032* | |
C13 | 0.8871 (4) | 0.5396 (3) | 0.4422 (2) | 0.0256 (6) | |
C14 | 0.8166 (4) | 0.6035 (3) | 0.3333 (3) | 0.0269 (6) | |
H14 | 0.7938 | 0.6974 | 0.3150 | 0.032* | |
C15 | 0.7729 (4) | 0.5457 (3) | 0.2434 (2) | 0.0266 (6) | |
H15 | 0.7907 | 0.4521 | 0.2589 | 0.032* | |
C16 | 1.0449 (5) | 1.1181 (3) | 0.8109 (3) | 0.0430 (8) | |
H16A | 1.1727 | 1.1035 | 0.8283 | 0.064* | |
H16B | 0.9987 | 1.2115 | 0.7725 | 0.064* | |
H16C | 1.0311 | 1.0624 | 0.7594 | 0.064* | |
C17 | 0.7356 (4) | 1.0966 (3) | 0.8971 (3) | 0.0386 (7) | |
H17D | 0.7279 | 1.0357 | 0.8489 | 0.058* | |
H17E | 0.6854 | 1.1879 | 0.8547 | 0.058* | |
H17F | 0.6670 | 1.0754 | 0.9695 | 0.058* | |
C18 | 1.1667 (4) | 0.7522 (3) | 1.1629 (3) | 0.0326 (7) | |
H18D | 1.2130 | 0.7046 | 1.1024 | 0.049* | |
H18E | 1.0831 | 0.7064 | 1.2141 | 0.049* | |
H18F | 1.2673 | 0.7548 | 1.2084 | 0.049* | |
C19 | 1.1066 (4) | 0.5018 (3) | 0.8899 (3) | 0.0306 (6) | |
H19D | 1.0184 | 0.4875 | 0.9531 | 0.046* | |
H19E | 1.2252 | 0.4905 | 0.9226 | 0.046* | |
H19F | 1.1134 | 0.4375 | 0.8427 | 0.046* | |
C20 | 0.9321 (4) | 0.3890 (3) | 0.4876 (3) | 0.0301 (6) | |
H20D | 0.8526 | 0.3640 | 0.5538 | 0.045* | |
H20E | 1.0579 | 0.3590 | 0.5125 | 0.045* | |
H20F | 0.9147 | 0.3474 | 0.4257 | 0.045* | |
C1B | 0.5262 (4) | 0.0926 (3) | −0.5234 (2) | 0.0288 (6) | |
C2B | 0.5945 (4) | −0.0060 (3) | −0.6028 (3) | 0.0295 (6) | |
H2B1 | 0.7085 | 0.0113 | −0.6417 | 0.035* | |
H2B2 | 0.6209 | −0.0977 | −0.5536 | 0.035* | |
C3B | 0.4587 (4) | 0.0045 (3) | −0.6955 (3) | 0.0311 (6) | |
H3B1 | 0.3480 | −0.0210 | −0.6554 | 0.037* | |
C4B | 0.4043 (4) | 0.1479 (3) | −0.7703 (2) | 0.0273 (6) | |
C5B | 0.3856 (4) | 0.2597 (3) | −0.7118 (2) | 0.0249 (6) | |
C6B | 0.4485 (4) | 0.2347 (3) | −0.6001 (2) | 0.0256 (6) | |
C7B | 0.4368 (4) | 0.3432 (3) | −0.5458 (2) | 0.0256 (6) | |
C8B | 0.4343 (4) | 0.4333 (3) | −0.4967 (2) | 0.0265 (6) | |
C9B | 0.4374 (4) | 0.5392 (3) | −0.4410 (2) | 0.0238 (6) | |
C10B | 0.4945 (4) | 0.5061 (3) | −0.3278 (2) | 0.0269 (6) | |
H10B | 0.5260 | 0.4141 | −0.2919 | 0.032* | |
C11B | 0.5123 (4) | 0.5946 (3) | −0.2569 (2) | 0.0250 (6) | |
H11B | 0.4822 | 0.6873 | −0.2897 | 0.030* | |
C12B | 0.5711 (4) | 0.5496 (3) | −0.1438 (2) | 0.0264 (6) | |
H12B | 0.5976 | 0.4563 | −0.1137 | 0.032* | |
C13B | 0.5977 (4) | 0.6285 (3) | −0.0644 (2) | 0.0251 (6) | |
C14B | 0.6637 (4) | 0.5635 (3) | 0.0458 (2) | 0.0261 (6) | |
H14B | 0.6834 | 0.4696 | 0.0642 | 0.031* | |
C15B | 0.7067 (4) | 0.6205 (3) | 0.1367 (3) | 0.0279 (6) | |
H15B | 0.6882 | 0.7141 | 0.1217 | 0.033* | |
C16B | 0.6881 (4) | 0.0925 (3) | −0.4508 (3) | 0.0404 (8) | |
H16D | 0.7357 | 0.0025 | −0.4045 | 0.061* | |
H16E | 0.6476 | 0.1523 | −0.3988 | 0.061* | |
H16F | 0.7828 | 0.1226 | −0.5032 | 0.061* | |
C17B | 0.3718 (5) | 0.0509 (3) | −0.4387 (3) | 0.0385 (7) | |
H17A | 0.2700 | 0.0497 | −0.4839 | 0.058* | |
H17B | 0.3321 | 0.1147 | −0.3902 | 0.058* | |
H17C | 0.4166 | −0.0376 | −0.3889 | 0.058* | |
C18B | 0.3024 (4) | 0.3984 (3) | −0.7835 (3) | 0.0327 (7) | |
H18A | 0.3078 | 0.4641 | −0.7399 | 0.049* | |
H18B | 0.1764 | 0.4037 | −0.7996 | 0.049* | |
H18C | 0.3696 | 0.4164 | −0.8569 | 0.049* | |
C19B | 0.3774 (4) | 0.6814 (3) | −0.5149 (3) | 0.0284 (6) | |
H19A | 0.3805 | 0.7443 | −0.4679 | 0.043* | |
H19B | 0.2544 | 0.6954 | −0.5420 | 0.043* | |
H19C | 0.4591 | 0.6954 | −0.5820 | 0.043* | |
C20B | 0.5514 (4) | 0.7809 (3) | −0.1085 (3) | 0.0295 (6) | |
H20A | 0.5672 | 0.8214 | −0.0455 | 0.044* | |
H20B | 0.4260 | 0.8109 | −0.1341 | 0.044* | |
H20C | 0.6316 | 0.8072 | −0.1739 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0563 (14) | 0.0333 (11) | 0.0446 (13) | −0.0041 (10) | −0.0034 (11) | −0.0226 (10) |
O4 | 0.0356 (11) | 0.0404 (12) | 0.0290 (12) | −0.0049 (9) | −0.0041 (9) | −0.0144 (9) |
O3B | 0.0526 (14) | 0.0269 (11) | 0.0406 (12) | 0.0010 (9) | −0.0039 (11) | −0.0186 (9) |
O4B | 0.0429 (12) | 0.0388 (12) | 0.0282 (12) | −0.0016 (10) | −0.0081 (9) | −0.0129 (9) |
C1 | 0.0354 (16) | 0.0227 (15) | 0.0274 (14) | −0.0060 (12) | −0.0047 (12) | −0.0042 (11) |
C2 | 0.0373 (16) | 0.0185 (13) | 0.0352 (15) | −0.0022 (11) | −0.0060 (13) | −0.0037 (11) |
C3 | 0.0347 (16) | 0.0273 (15) | 0.0354 (16) | −0.0047 (12) | −0.0018 (12) | −0.0151 (12) |
C4 | 0.0274 (14) | 0.0280 (14) | 0.0280 (15) | −0.0074 (11) | −0.0012 (12) | −0.0091 (12) |
C5 | 0.0269 (15) | 0.0223 (14) | 0.0288 (15) | −0.0072 (11) | 0.0003 (12) | −0.0066 (12) |
C6 | 0.0278 (15) | 0.0222 (14) | 0.0248 (15) | −0.0033 (12) | −0.0003 (12) | −0.0082 (12) |
C7 | 0.0285 (15) | 0.0262 (15) | 0.0275 (15) | −0.0027 (12) | −0.0022 (12) | −0.0041 (13) |
C8 | 0.0295 (15) | 0.0269 (15) | 0.0251 (14) | −0.0029 (12) | −0.0004 (12) | −0.0085 (13) |
C9 | 0.0256 (15) | 0.0262 (15) | 0.0295 (16) | −0.0048 (12) | −0.0008 (13) | −0.0096 (13) |
C10 | 0.0267 (15) | 0.0231 (14) | 0.0288 (15) | −0.0040 (11) | 0.0002 (12) | −0.0083 (12) |
C11 | 0.0250 (15) | 0.0242 (15) | 0.0311 (17) | −0.0015 (12) | −0.0012 (13) | −0.0072 (13) |
C12 | 0.0289 (15) | 0.0227 (14) | 0.0276 (15) | −0.0021 (12) | −0.0016 (12) | −0.0078 (12) |
C13 | 0.0231 (14) | 0.0261 (15) | 0.0280 (15) | −0.0037 (12) | 0.0005 (12) | −0.0090 (12) |
C14 | 0.0290 (15) | 0.0223 (14) | 0.0292 (14) | −0.0020 (12) | −0.0008 (12) | −0.0092 (12) |
C15 | 0.0258 (14) | 0.0255 (15) | 0.0268 (16) | −0.0021 (12) | 0.0004 (12) | −0.0070 (12) |
C16 | 0.057 (2) | 0.0363 (17) | 0.0328 (16) | −0.0123 (15) | 0.0011 (15) | −0.0017 (14) |
C17 | 0.0453 (18) | 0.0245 (15) | 0.0422 (17) | 0.0012 (13) | −0.0135 (14) | −0.0060 (13) |
C18 | 0.0421 (18) | 0.0252 (14) | 0.0276 (15) | −0.0023 (13) | −0.0094 (13) | −0.0036 (12) |
C19 | 0.0371 (16) | 0.0289 (15) | 0.0277 (15) | −0.0068 (13) | −0.0013 (13) | −0.0106 (12) |
C20 | 0.0354 (16) | 0.0292 (15) | 0.0256 (14) | −0.0044 (12) | −0.0046 (12) | −0.0076 (12) |
C1B | 0.0352 (16) | 0.0201 (14) | 0.0292 (15) | −0.0024 (12) | −0.0057 (12) | −0.0043 (12) |
C2B | 0.0305 (15) | 0.0204 (13) | 0.0345 (15) | −0.0015 (11) | −0.0037 (12) | −0.0040 (11) |
C3B | 0.0360 (15) | 0.0227 (14) | 0.0356 (16) | −0.0019 (12) | −0.0028 (12) | −0.0128 (12) |
C4B | 0.0238 (14) | 0.0308 (15) | 0.0280 (16) | −0.0045 (11) | −0.0018 (11) | −0.0094 (12) |
C5B | 0.0263 (15) | 0.0230 (14) | 0.0257 (15) | −0.0034 (11) | −0.0013 (12) | −0.0082 (11) |
C6B | 0.0252 (14) | 0.0216 (14) | 0.0292 (16) | −0.0030 (11) | 0.0015 (12) | −0.0072 (12) |
C7B | 0.0288 (15) | 0.0252 (15) | 0.0218 (14) | −0.0040 (12) | −0.0053 (12) | −0.0046 (12) |
C8B | 0.0250 (15) | 0.0255 (15) | 0.0251 (14) | −0.0008 (11) | −0.0058 (12) | −0.0016 (12) |
C9B | 0.0250 (15) | 0.0234 (14) | 0.0243 (14) | −0.0043 (12) | 0.0011 (12) | −0.0094 (12) |
C10B | 0.0252 (15) | 0.0237 (14) | 0.0313 (16) | −0.0023 (12) | −0.0011 (12) | −0.0087 (12) |
C11B | 0.0243 (15) | 0.0235 (15) | 0.0262 (15) | −0.0015 (12) | −0.0017 (12) | −0.0074 (12) |
C12B | 0.0267 (15) | 0.0232 (14) | 0.0278 (15) | −0.0018 (12) | −0.0020 (12) | −0.0065 (12) |
C13B | 0.0240 (15) | 0.0252 (15) | 0.0261 (15) | −0.0029 (12) | −0.0014 (12) | −0.0085 (12) |
C14B | 0.0277 (15) | 0.0236 (14) | 0.0277 (15) | −0.0014 (12) | −0.0010 (12) | −0.0112 (12) |
C15B | 0.0280 (15) | 0.0263 (15) | 0.0294 (16) | −0.0032 (12) | 0.0006 (12) | −0.0098 (13) |
C16B | 0.0526 (19) | 0.0250 (15) | 0.0400 (18) | 0.0036 (14) | −0.0214 (15) | −0.0070 (13) |
C17B | 0.0526 (19) | 0.0239 (14) | 0.0338 (16) | −0.0058 (13) | 0.0061 (14) | −0.0016 (12) |
C18B | 0.0428 (17) | 0.0235 (15) | 0.0293 (15) | −0.0011 (13) | −0.0049 (13) | −0.0064 (12) |
C19B | 0.0333 (15) | 0.0237 (14) | 0.0289 (16) | −0.0054 (12) | −0.0039 (12) | −0.0074 (12) |
C20B | 0.0341 (16) | 0.0265 (14) | 0.0278 (15) | −0.0048 (12) | −0.0053 (12) | −0.0072 (12) |
O3—C3 | 1.418 (3) | C20—H20D | 0.9600 |
O3—H3 | 0.8200 | C20—H20E | 0.9600 |
O4—C4 | 1.228 (3) | C20—H20F | 0.9600 |
O3B—C3B | 1.412 (3) | C1B—C16B | 1.524 (4) |
O3B—H3B | 0.8200 | C1B—C2B | 1.530 (4) |
O4B—C4B | 1.218 (3) | C1B—C17B | 1.535 (4) |
C1—C16 | 1.521 (4) | C1B—C6B | 1.535 (4) |
C1—C17 | 1.532 (4) | C2B—C3B | 1.501 (4) |
C1—C2 | 1.534 (4) | C2B—H2B1 | 0.9700 |
C1—C6 | 1.536 (4) | C2B—H2B2 | 0.9700 |
C2—C3 | 1.501 (4) | C3B—C4B | 1.513 (4) |
C2—H2A | 0.9700 | C3B—H3B1 | 0.9800 |
C2—H2B | 0.9700 | C4B—C5B | 1.471 (4) |
C3—C4 | 1.513 (4) | C5B—C6B | 1.356 (4) |
C3—H3A | 0.9800 | C5B—C18B | 1.496 (4) |
C4—C5 | 1.460 (4) | C6B—C7B | 1.414 (4) |
C5—C6 | 1.354 (4) | C7B—C8B | 1.215 (4) |
C5—C18 | 1.503 (4) | C8B—C9B | 1.422 (4) |
C6—C7 | 1.429 (4) | C9B—C10B | 1.350 (4) |
C7—C8 | 1.207 (4) | C9B—C19B | 1.504 (4) |
C8—C9 | 1.418 (4) | C10B—C11B | 1.418 (4) |
C9—C10 | 1.352 (4) | C10B—H10B | 0.9300 |
C9—C19 | 1.507 (4) | C11B—C12B | 1.351 (4) |
C10—C11 | 1.434 (4) | C11B—H11B | 0.9300 |
C10—H10 | 0.9300 | C12B—C13B | 1.434 (4) |
C11—C12 | 1.347 (4) | C12B—H12B | 0.9300 |
C11—H11 | 0.9300 | C13B—C14B | 1.360 (4) |
C12—C13 | 1.437 (4) | C13B—C20B | 1.513 (4) |
C12—H12 | 0.9300 | C14B—C15B | 1.425 (4) |
C13—C14 | 1.356 (4) | C14B—H14B | 0.9300 |
C13—C20 | 1.496 (4) | C15B—H15B | 0.9300 |
C14—C15 | 1.422 (4) | C16B—H16D | 0.9600 |
C14—H14 | 0.9300 | C16B—H16E | 0.9600 |
C15—C15B | 1.349 (3) | C16B—H16F | 0.9600 |
C15—H15 | 0.9300 | C17B—H17A | 0.9600 |
C16—H16A | 0.9600 | C17B—H17B | 0.9600 |
C16—H16B | 0.9600 | C17B—H17C | 0.9600 |
C16—H16C | 0.9600 | C18B—H18A | 0.9600 |
C17—H17D | 0.9600 | C18B—H18B | 0.9600 |
C17—H17E | 0.9600 | C18B—H18C | 0.9600 |
C17—H17F | 0.9600 | C19B—H19A | 0.9600 |
C18—H18D | 0.9600 | C19B—H19B | 0.9600 |
C18—H18E | 0.9600 | C19B—H19C | 0.9600 |
C18—H18F | 0.9600 | C20B—H20A | 0.9600 |
C19—H19D | 0.9600 | C20B—H20B | 0.9600 |
C19—H19E | 0.9600 | C20B—H20C | 0.9600 |
C19—H19F | 0.9600 | ||
C3—O3—H3 | 109.5 | H20E—C20—H20F | 109.5 |
C3B—O3B—H3B | 109.5 | C16B—C1B—C2B | 108.0 (2) |
C16—C1—C17 | 109.4 (3) | C16B—C1B—C17B | 109.1 (3) |
C16—C1—C2 | 108.4 (2) | C2B—C1B—C17B | 111.5 (2) |
C17—C1—C2 | 111.0 (2) | C16B—C1B—C6B | 110.9 (2) |
C16—C1—C6 | 109.4 (2) | C2B—C1B—C6B | 109.9 (2) |
C17—C1—C6 | 109.4 (2) | C17B—C1B—C6B | 107.5 (2) |
C2—C1—C6 | 109.3 (2) | C3B—C2B—C1B | 113.2 (2) |
C3—C2—C1 | 112.0 (2) | C3B—C2B—H2B1 | 108.9 |
C3—C2—H2A | 109.2 | C1B—C2B—H2B1 | 108.9 |
C1—C2—H2A | 109.2 | C3B—C2B—H2B2 | 108.9 |
C3—C2—H2B | 109.2 | C1B—C2B—H2B2 | 108.9 |
C1—C2—H2B | 109.2 | H2B1—C2B—H2B2 | 107.8 |
H2A—C2—H2B | 107.9 | O3B—C3B—C2B | 110.8 (2) |
O3—C3—C2 | 112.2 (2) | O3B—C3B—C4B | 109.8 (2) |
O3—C3—C4 | 110.5 (2) | C2B—C3B—C4B | 111.1 (2) |
C2—C3—C4 | 109.1 (2) | O3B—C3B—H3B1 | 108.4 |
O3—C3—H3A | 108.3 | C2B—C3B—H3B1 | 108.4 |
C2—C3—H3A | 108.3 | C4B—C3B—H3B1 | 108.4 |
C4—C3—H3A | 108.3 | O4B—C4B—C5B | 122.9 (3) |
O4—C4—C5 | 123.2 (2) | O4B—C4B—C3B | 118.9 (3) |
O4—C4—C3 | 119.1 (2) | C5B—C4B—C3B | 118.2 (2) |
C5—C4—C3 | 117.6 (2) | C6B—C5B—C4B | 119.9 (2) |
C6—C5—C4 | 119.6 (2) | C6B—C5B—C18B | 123.5 (3) |
C6—C5—C18 | 123.0 (2) | C4B—C5B—C18B | 116.5 (2) |
C4—C5—C18 | 117.4 (2) | C5B—C6B—C7B | 119.8 (2) |
C5—C6—C7 | 119.3 (2) | C5B—C6B—C1B | 124.1 (3) |
C5—C6—C1 | 124.6 (2) | C7B—C6B—C1B | 116.1 (2) |
C7—C6—C1 | 116.1 (2) | C8B—C7B—C6B | 177.0 (3) |
C8—C7—C6 | 174.7 (3) | C7B—C8B—C9B | 178.0 (3) |
C7—C8—C9 | 176.1 (3) | C10B—C9B—C8B | 118.5 (2) |
C10—C9—C8 | 119.3 (3) | C10B—C9B—C19B | 124.9 (3) |
C10—C9—C19 | 124.6 (3) | C8B—C9B—C19B | 116.6 (2) |
C8—C9—C19 | 116.1 (2) | C9B—C10B—C11B | 127.8 (3) |
C9—C10—C11 | 127.7 (3) | C9B—C10B—H10B | 116.1 |
C9—C10—H10 | 116.2 | C11B—C10B—H10B | 116.1 |
C11—C10—H10 | 116.2 | C12B—C11B—C10B | 122.6 (3) |
C12—C11—C10 | 122.6 (3) | C12B—C11B—H11B | 118.7 |
C12—C11—H11 | 118.7 | C10B—C11B—H11B | 118.7 |
C10—C11—H11 | 118.7 | C11B—C12B—C13B | 127.8 (3) |
C11—C12—C13 | 127.8 (3) | C11B—C12B—H12B | 116.1 |
C11—C12—H12 | 116.1 | C13B—C12B—H12B | 116.1 |
C13—C12—H12 | 116.1 | C14B—C13B—C12B | 118.9 (3) |
C14—C13—C12 | 117.8 (3) | C14B—C13B—C20B | 123.2 (3) |
C14—C13—C20 | 123.5 (3) | C12B—C13B—C20B | 117.9 (2) |
C12—C13—C20 | 118.7 (2) | C13B—C14B—C15B | 128.4 (3) |
C13—C14—C15 | 128.5 (3) | C13B—C14B—H14B | 115.8 |
C13—C14—H14 | 115.7 | C15B—C14B—H14B | 115.8 |
C15—C14—H14 | 115.7 | C15—C15B—C14B | 123.4 (2) |
C15B—C15—C14 | 123.0 (2) | C15—C15B—H15B | 118.3 |
C15B—C15—H15 | 118.5 | C14B—C15B—H15B | 118.3 |
C14—C15—H15 | 118.5 | C1B—C16B—H16D | 109.5 |
C1—C16—H16A | 109.5 | C1B—C16B—H16E | 109.5 |
C1—C16—H16B | 109.5 | H16D—C16B—H16E | 109.5 |
H16A—C16—H16B | 109.5 | C1B—C16B—H16F | 109.5 |
C1—C16—H16C | 109.5 | H16D—C16B—H16F | 109.5 |
H16A—C16—H16C | 109.5 | H16E—C16B—H16F | 109.5 |
H16B—C16—H16C | 109.5 | C1B—C17B—H17A | 109.5 |
C1—C17—H17D | 109.5 | C1B—C17B—H17B | 109.5 |
C1—C17—H17E | 109.5 | H17A—C17B—H17B | 109.5 |
H17D—C17—H17E | 109.5 | C1B—C17B—H17C | 109.5 |
C1—C17—H17F | 109.5 | H17A—C17B—H17C | 109.5 |
H17D—C17—H17F | 109.5 | H17B—C17B—H17C | 109.5 |
H17E—C17—H17F | 109.5 | C5B—C18B—H18A | 109.5 |
C5—C18—H18D | 109.5 | C5B—C18B—H18B | 109.5 |
C5—C18—H18E | 109.5 | H18A—C18B—H18B | 109.5 |
H18D—C18—H18E | 109.5 | C5B—C18B—H18C | 109.5 |
C5—C18—H18F | 109.5 | H18A—C18B—H18C | 109.5 |
H18D—C18—H18F | 109.5 | H18B—C18B—H18C | 109.5 |
H18E—C18—H18F | 109.5 | C9B—C19B—H19A | 109.5 |
C9—C19—H19D | 109.5 | C9B—C19B—H19B | 109.5 |
C9—C19—H19E | 109.5 | H19A—C19B—H19B | 109.5 |
H19D—C19—H19E | 109.5 | C9B—C19B—H19C | 109.5 |
C9—C19—H19F | 109.5 | H19A—C19B—H19C | 109.5 |
H19D—C19—H19F | 109.5 | H19B—C19B—H19C | 109.5 |
H19E—C19—H19F | 109.5 | C13B—C20B—H20A | 109.5 |
C13—C20—H20D | 109.5 | C13B—C20B—H20B | 109.5 |
C13—C20—H20E | 109.5 | H20A—C20B—H20B | 109.5 |
H20D—C20—H20E | 109.5 | C13B—C20B—H20C | 109.5 |
C13—C20—H20F | 109.5 | H20A—C20B—H20C | 109.5 |
H20D—C20—H20F | 109.5 | H20B—C20B—H20C | 109.5 |
C16—C1—C2—C3 | −165.6 (3) | C17B—C1B—C2B—C3B | 71.3 (3) |
C17—C1—C2—C3 | 74.2 (3) | C6B—C1B—C2B—C3B | −47.7 (3) |
C6—C1—C2—C3 | −46.5 (3) | C1B—C2B—C3B—O3B | 177.6 (2) |
C1—C2—C3—O3 | −175.9 (2) | C1B—C2B—C3B—C4B | 55.4 (3) |
C1—C2—C3—C4 | 61.3 (3) | O3B—C3B—C4B—O4B | 20.8 (4) |
O3—C3—C4—O4 | 19.1 (4) | C2B—C3B—C4B—O4B | 143.6 (3) |
C2—C3—C4—O4 | 142.8 (3) | O3B—C3B—C4B—C5B | −159.5 (2) |
O3—C3—C4—C5 | −164.1 (2) | C2B—C3B—C4B—C5B | −36.7 (3) |
C2—C3—C4—C5 | −40.4 (3) | O4B—C4B—C5B—C6B | −168.2 (3) |
O4—C4—C5—C6 | −177.8 (3) | C3B—C4B—C5B—C6B | 12.0 (4) |
C3—C4—C5—C6 | 5.6 (4) | O4B—C4B—C5B—C18B | 9.4 (4) |
O4—C4—C5—C18 | 4.7 (4) | C3B—C4B—C5B—C18B | −170.3 (3) |
C3—C4—C5—C18 | −171.9 (3) | C4B—C5B—C6B—C7B | 177.5 (2) |
C4—C5—C6—C7 | −169.1 (2) | C18B—C5B—C6B—C7B | 0.0 (4) |
C18—C5—C6—C7 | 8.2 (4) | C4B—C5B—C6B—C1B | −5.4 (4) |
C4—C5—C6—C1 | 9.9 (4) | C18B—C5B—C6B—C1B | 177.2 (3) |
C18—C5—C6—C1 | −172.7 (3) | C16B—C1B—C6B—C5B | 142.3 (3) |
C16—C1—C6—C5 | 129.2 (3) | C2B—C1B—C6B—C5B | 23.0 (4) |
C17—C1—C6—C5 | −111.0 (3) | C17B—C1B—C6B—C5B | −98.6 (3) |
C2—C1—C6—C5 | 10.7 (4) | C16B—C1B—C6B—C7B | −40.5 (3) |
C16—C1—C6—C7 | −51.7 (3) | C2B—C1B—C6B—C7B | −159.8 (2) |
C17—C1—C6—C7 | 68.1 (3) | C17B—C1B—C6B—C7B | 78.6 (3) |
C2—C1—C6—C7 | −170.2 (2) | C5B—C6B—C7B—C8B | −145 (5) |
C5—C6—C7—C8 | 78 (3) | C1B—C6B—C7B—C8B | 37 (5) |
C1—C6—C7—C8 | −101 (3) | C6B—C7B—C8B—C9B | 58 (11) |
C6—C7—C8—C9 | −44 (7) | C7B—C8B—C9B—C10B | −98 (8) |
C7—C8—C9—C10 | 148 (4) | C7B—C8B—C9B—C19B | 82 (8) |
C7—C8—C9—C19 | −30 (5) | C8B—C9B—C10B—C11B | 178.4 (3) |
C8—C9—C10—C11 | −175.2 (3) | C19B—C9B—C10B—C11B | −0.9 (5) |
C19—C9—C10—C11 | 2.8 (5) | C9B—C10B—C11B—C12B | 179.9 (3) |
C9—C10—C11—C12 | 177.9 (3) | C10B—C11B—C12B—C13B | 178.8 (3) |
C10—C11—C12—C13 | −177.8 (3) | C11B—C12B—C13B—C14B | −178.0 (3) |
C11—C12—C13—C14 | 176.4 (3) | C11B—C12B—C13B—C20B | 1.6 (4) |
C11—C12—C13—C20 | −2.7 (4) | C12B—C13B—C14B—C15B | 177.5 (2) |
C12—C13—C14—C15 | −179.2 (3) | C20B—C13B—C14B—C15B | −2.1 (4) |
C20—C13—C14—C15 | −0.2 (5) | C14—C15—C15B—C14B | 179.5 (3) |
C13—C14—C15—C15B | −178.4 (3) | C13B—C14B—C15B—C15 | −179.6 (3) |
C16B—C1B—C2B—C3B | −168.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.82 | 2.17 | 2.648 (3) | 117 |
O3B—H3B···O4B | 0.82 | 2.19 | 2.629 (3) | 114 |
Experimental details
(s-cis-1) | (s-trans-1) | (2) | (3) | |
Crystal data | ||||
Chemical formula | C44H56O6·0.44(C4H8O2) | C44H56O6 | C40H50O4 | C40H48O4 |
Mr | 719.59 | 680.89 | 594.80 | 592.78 |
Crystal system, space group | Monoclinic, C2/c | Monoclinic, P21/c | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 100 | 100 | 100 | 100 |
a, b, c (Å) | 12.9673 (15), 10.7883 (13), 30.264 (4) | 10.6598 (10), 10.1683 (10), 18.2940 (18) | 7.7821 (4), 9.9578 (5), 11.4162 (5) | 7.4769 (14), 10.4729 (19), 11.633 (2) |
α, β, γ (°) | 90, 101.796 (1), 90 | 90, 100.700 (2), 90 | 88.126 (1), 78.329 (1), 84.340 (1) | 75.606 (2), 85.901 (2), 76.389 (2) |
V (Å3) | 4144.3 (8) | 1948.4 (3) | 862.08 (7) | 857.5 (3) |
Z | 4 | 2 | 1 | 1 |
Radiation type | Mo Kα | Mo Kα | Synchrotron, λ = 0.6709 Å | Synchrotron, λ = 0.67100 Å |
µ (mm−1) | 0.08 | 0.08 | 0.07 | 0.07 |
Crystal size (mm) | 0.60 × 0.60 × 0.05 | 0.60 × 0.60 × 0.10 | 0.2 × 0.2 × 0.02 | 0.04 × 0.03 × 0.01 |
Data collection | ||||
Diffractometer | Bruker APEX CCD area detector diffractometer | Bruker APEX CCD area detector diffractometer | Bruker APEXII CCD area detector diffractometer | Bruker APEXII CCD area detector diffractometer |
Absorption correction | – | – | Multi-scan SADABS | Multi-scan SADABS |
Tmin, Tmax | – | – | 0.736, 1.000 | 0.749, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13064, 3632, 2913 | 9816, 3425, 2506 | 6688, 3029, 2910 | 14633, 4002, 2799 |
Rint | 0.076 | 0.072 | 0.016 | 0.062 |
(sin θ/λ)max (Å−1) | 0.595 | 0.595 | 0.602 | 0.655 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.085, 0.218, 1.11 | 0.065, 0.175, 1.08 | 0.046, 0.126, 1.08 | 0.042, 0.105, 1.01 |
No. of reflections | 3632 | 3425 | 3029 | 4002 |
No. of parameters | 304 | 305 | 428 | 409 |
No. of restraints | 117 | 73 | 143 | 3 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0625P)2 + 15.0678P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0489P)2 + 1.5414P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0747P)2 + 0.1591P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0581P)2] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.54, −0.28 | 0.39, −0.21 | 0.17, −0.16 | 0.19, −0.17 |
Computer programs: Bruker SMART, Bruker SAINT, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Bruker SHELXTL; PLATON (Spek,2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.82 | 2.25 | 2.669 (4) | 111.8 |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.82 | 2.17 | 2.648 (3) | 117.4 |
O3B—H3B···O4B | 0.82 | 2.19 | 2.629 (3) | 113.5 |
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