The structure of the title compound, C25H36O5, was refined in space group P1, with Z' = 4. The high value for Z' is due to a degree of free rotation around the ester bond C-O at the 3 position of the steroidal A-D nucleus.
Supporting information
CCDC reference: 222900
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.066
- wR factor = 0.191
- Data-to-parameter ratio = 7.4
checkCIF/PLATON results
No syntax errors found
Alert level B
DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00
_refine_diff_density_max given = 0.961
Test value = 0.800
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.47
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 0.96 e/A 3
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.39 Ratio
PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C1
PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C11
PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C12
PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C107
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C21
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C25
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C225
Alert level C
DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
REFNR01_ALERT_3_C Ratio of reflections to parameters is < 8 for a
non-centrosymmetric structure, where ZMAX < 18
sine(theta)/lambda -0.1862
Proportion of unique data used 1.0000
Ratio reflections to parameters 7.3845
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.38
PLAT213_ALERT_2_C Atom O22 has ADP max/min Ratio ............. 3.30 prolat
PLAT213_ALERT_2_C Atom C11 has ADP max/min Ratio ............. 3.10 prolat
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.18 Ratio
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.57 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.50 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.24 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C213 - C218 = 6.08 su
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C24
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C116
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C124
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O320
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C324
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C5
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C8
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C9
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C10
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C13
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C23
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C113
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C123
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C125
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C128
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C228
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C321
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C325
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C328
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.50
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.14
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.22
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O29
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT355_ALERT_3_C Long O-H Bond (0.82A) O327 - H327 = 1.04 Ang.
PLAT362_ALERT_2_C Short C(sp3)-C(sp2) Bond C28 - C30 = 1.37 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 7990
Count of symmetry unique reflns 8015
Completeness (_total/calc) 99.69%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
11 ALERT level B = Potentially serious problem
36 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
40 ALERT type 2 Indicator that the structure model may be wrong or deficient
6 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
In a round-bottomed flask, pregnenolone (1 g, 3.16 mmol) was dissolved in pyridine (20 ml) and succinic anhydride (3.6 g, 36 mmol) was added under a nitrogen atmosphere with magnetic stirring. The reaction was stirred at 373 K for 2.5 h. After cooling to room temperature, the mixture was poured over 100 ml of distilled water and the pH adjusted to 3 with dilute HCl (1:3). The white solid was filtered off, washed repeatedly with distilled water and dried at 333 K under vacuum to obtain 1.19 g of (I) as white microcrystals (yield 90%, m. p. 452–454 K). Analysis found: C 71.9, H 8.6, O 19.1%; calculated for C25H36O5: C 72.1, H 8.7, O 19.2%. Spectroscopic data are in agreement with the X-ray structure. IR (CsI pellets) ν(C═O) 1734, 1704 cm−1, ν(C—O) 1322, 1090 cm−1; FAB+ m/z 417 [M+, 13%]; 13C NMR displacement for C3, pregnenolone: δ = 71.65 p.p.m., (I): δ = 74.41 p.p.m.
Due to the poor data-to-parameters ratio, non-H atoms were refined anisotropically, with atoms closer than 1.7 Å restrained, with an effective standard uncertainty of 0.04 Å2, to have the same Uij components. H atoms bonded to sp3– or sp2-hybridized C atoms were placed at idealized positions. H atoms of the hydroxyl groups were found in difference maps. In order to avoid H···H bumping involving H30C belonging to the C30 methyl of the acetyl group in the first independent molecule, this methyl was first allowed to rotate about the C28—C30 bond, afterwards its torsion geometry was fixed. In the final cycles, all H atoms were constrained to ride on their parent atoms, with Uiso(H) = xUeq(parent), where constrained distances (Å) and x parameters are: aromatic C—H 0.93 and x = 1.2, methine C—H 0.98 and x = 1.2, methylene C—H 0.97 and x = 1.2, methyl C—H 0.98 and x = 1.5, and hydroxyl O—H distance found from difference maps and x = 1.5. The highest residual peak observed in the final difference map is located in the vicinity of the C28/O29/C30 acetyl group, at 1.67 Å from C28. Its quite large value is attributable to the fact that this group displays large thermal motions. The Ueq parameter for O29, for example, is the largest observed for the overall asymmetric unit, Ueq = 0.224 (5) Å2.
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury 1.1.2 (CCDC, 2002); software used to prepare material for publication: SHELXTL-Plus.
Succinic acid mono(17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14, 15,16,17-tetradecahydro-1
H-cyclopenta[
a]phenanthren-3-yl) ester
top
Crystal data top
C25H36O5 | Z = 4 |
Mr = 416.54 | F(000) = 904 |
Triclinic, P1 | Dx = 1.213 Mg m−3 |
Hall symbol: P 1 | Melting point: 452-454 K K |
a = 11.4692 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.8174 (12) Å | Cell parameters from 50 reflections |
c = 17.6837 (14) Å | θ = 2.4–12.0° |
α = 96.925 (9)° | µ = 0.08 mm−1 |
β = 104.907 (6)° | T = 298 K |
γ = 95.201 (8)° | Irregular, colourless |
V = 2280.7 (4) Å3 | 0.5 × 0.3 × 0.3 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.031 |
Radiation source: fine-focus sealed tube, FN4 | θmax = 25.0°, θmin = 1.8° |
Graphite monochromator | h = −1→13 |
2θ/ω scans | k = −13→13 |
9296 measured reflections | l = −21→20 |
7990 independent reflections | 2 standard reflections every 98 reflections |
5778 reflections with I > 2σ(I) | intensity decay: 0.5% |
Refinement top
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)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.191 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.26 | (Δ/σ)max < 0.001 |
7990 reflections | Δρmax = 0.96 e Å−3 |
1082 parameters | Δρmin = −0.22 e Å−3 |
795 restraints | Extinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0083 (17) |
Crystal data top
C25H36O5 | γ = 95.201 (8)° |
Mr = 416.54 | V = 2280.7 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.4692 (10) Å | Mo Kα radiation |
b = 11.8174 (12) Å | µ = 0.08 mm−1 |
c = 17.6837 (14) Å | T = 298 K |
α = 96.925 (9)° | 0.5 × 0.3 × 0.3 mm |
β = 104.907 (6)° | |
Data collection top
Bruker P4 diffractometer | Rint = 0.031 |
9296 measured reflections | 2 standard reflections every 98 reflections |
7990 independent reflections | intensity decay: 0.5% |
5778 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.066 | 795 restraints |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.26 | Δρmax = 0.96 e Å−3 |
7990 reflections | Δρmin = −0.22 e Å−3 |
1082 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.6706 (8) | −0.0481 (7) | 0.7730 (7) | 0.140 (4) | |
H1A | 0.5918 | −0.0475 | 0.7837 | 0.168* | |
H1B | 0.6653 | −0.0178 | 0.7238 | 0.168* | |
C2 | 0.6981 (8) | −0.1730 (7) | 0.7623 (7) | 0.125 (3) | |
H2A | 0.6954 | −0.2071 | 0.8091 | 0.150* | |
H2B | 0.6373 | −0.2175 | 0.7174 | 0.150* | |
C3 | 0.8206 (8) | −0.1750 (5) | 0.7490 (4) | 0.087 (2) | |
H3A | 0.8234 | −0.1432 | 0.7007 | 0.104* | |
C4 | 0.9173 (7) | −0.1090 (5) | 0.8195 (4) | 0.0810 (18) | |
H4A | 0.9966 | −0.1103 | 0.8095 | 0.097* | |
H4B | 0.9182 | −0.1452 | 0.8660 | 0.097* | |
C5 | 0.8920 (5) | 0.0151 (5) | 0.8343 (3) | 0.0639 (14) | |
C6 | 0.9754 (6) | 0.1001 (6) | 0.8398 (4) | 0.0795 (18) | |
H6A | 1.0501 | 0.0814 | 0.8341 | 0.095* | |
C7 | 0.9627 (6) | 0.2240 (5) | 0.8542 (4) | 0.0715 (16) | |
H7A | 0.9598 | 0.2565 | 0.8061 | 0.086* | |
H7B | 1.0339 | 0.2629 | 0.8946 | 0.086* | |
C8 | 0.8507 (4) | 0.2464 (4) | 0.8802 (3) | 0.0525 (12) | |
H8A | 0.8654 | 0.2364 | 0.9360 | 0.063* | |
C9 | 0.7438 (5) | 0.1585 (5) | 0.8312 (4) | 0.0772 (18) | |
H9A | 0.7377 | 0.1652 | 0.7757 | 0.093* | |
C10 | 0.7673 (6) | 0.0331 (5) | 0.8410 (4) | 0.0786 (18) | |
C11 | 0.6225 (6) | 0.1858 (7) | 0.8450 (8) | 0.161 (5) | |
H11A | 0.6213 | 0.1738 | 0.8981 | 0.193* | |
H11B | 0.5569 | 0.1337 | 0.8079 | 0.193* | |
C12 | 0.6012 (7) | 0.3133 (8) | 0.8343 (9) | 0.167 (5) | |
H12A | 0.5981 | 0.3250 | 0.7805 | 0.200* | |
H12B | 0.5242 | 0.3285 | 0.8441 | 0.200* | |
C13 | 0.7045 (6) | 0.3948 (6) | 0.8921 (5) | 0.092 (2) | |
C14 | 0.8208 (5) | 0.3678 (5) | 0.8723 (3) | 0.0570 (13) | |
H14A | 0.8069 | 0.3736 | 0.8159 | 0.068* | |
C15 | 0.9135 (5) | 0.4704 (5) | 0.9155 (4) | 0.0675 (15) | |
H15A | 0.9756 | 0.4829 | 0.8881 | 0.081* | |
H15B | 0.9521 | 0.4588 | 0.9692 | 0.081* | |
C16 | 0.8396 (6) | 0.5724 (5) | 0.9156 (4) | 0.0785 (17) | |
H16A | 0.8644 | 0.6276 | 0.8846 | 0.094* | |
H16B | 0.8512 | 0.6106 | 0.9692 | 0.094* | |
C17 | 0.7057 (6) | 0.5213 (6) | 0.8787 (6) | 0.100 (2) | |
H17A | 0.6925 | 0.5191 | 0.8215 | 0.120* | |
C18 | 0.7144 (10) | 0.3866 (8) | 0.9819 (7) | 0.136 (4) | |
H18A | 0.7526 | 0.3203 | 0.9962 | 0.204* | |
H18B | 0.6344 | 0.3798 | 0.9898 | 0.204* | |
H18C | 0.7621 | 0.4545 | 1.0144 | 0.204* | |
C19 | 0.7605 (11) | −0.0003 (7) | 0.9229 (6) | 0.130 (4) | |
H19A | 0.8262 | 0.0433 | 0.9641 | 0.195* | |
H19B | 0.7666 | −0.0808 | 0.9228 | 0.195* | |
H19C | 0.6844 | 0.0161 | 0.9322 | 0.195* | |
O20 | 0.8426 (5) | −0.2954 (4) | 0.7413 (3) | 0.0918 (14) | |
C21 | 0.8937 (6) | −0.3318 (5) | 0.6858 (4) | 0.0723 (16) | |
O22 | 0.9151 (10) | −0.2736 (5) | 0.6422 (6) | 0.203 (5) | |
C23 | 0.9162 (6) | −0.4523 (5) | 0.6856 (3) | 0.0674 (15) | |
H23A | 0.8457 | −0.4972 | 0.6925 | 0.081* | |
H23B | 0.9849 | −0.4570 | 0.7300 | 0.081* | |
C24 | 0.9419 (9) | −0.5029 (6) | 0.6106 (5) | 0.095 (2) | |
H24A | 0.8743 | −0.4943 | 0.5665 | 0.114* | |
H24B | 1.0135 | −0.4581 | 0.6049 | 0.114* | |
C25 | 0.9617 (6) | −0.6237 (5) | 0.6040 (4) | 0.0687 (15) | |
O26 | 0.9666 (5) | −0.6815 (4) | 0.6556 (3) | 0.0868 (13) | |
O27 | 0.9703 (7) | −0.6656 (4) | 0.5356 (3) | 0.129 (2) | |
H27 | 0.9730 | −0.7394 | 0.5203 | 0.193* | |
C28 | 0.6143 (8) | 0.5881 (8) | 0.8987 (9) | 0.154 (5) | |
O29 | 0.6307 (9) | 0.6800 (11) | 0.9559 (7) | 0.224 (5) | |
C30 | 0.5165 (8) | 0.5820 (9) | 0.8340 (7) | 0.135 (4) | |
H30A | 0.5051 | 0.5080 | 0.8022 | 0.202* | |
H30B | 0.5311 | 0.6408 | 0.8033 | 0.202* | |
H30C | 0.4450 | 0.5929 | 0.8512 | 0.202* | |
C101 | 0.3005 (5) | 0.3165 (4) | 0.5268 (3) | 0.0603 (13) | |
H10A | 0.2324 | 0.2813 | 0.4827 | 0.072* | |
H10B | 0.2914 | 0.2848 | 0.5733 | 0.072* | |
C102 | 0.2944 (6) | 0.4449 (5) | 0.5403 (4) | 0.0722 (16) | |
H10C | 0.2957 | 0.4769 | 0.4925 | 0.087* | |
H10D | 0.2191 | 0.4589 | 0.5531 | 0.087* | |
C103 | 0.4001 (6) | 0.5018 (4) | 0.6067 (3) | 0.0617 (14) | |
H10E | 0.3963 | 0.4712 | 0.6552 | 0.074* | |
C104 | 0.5205 (6) | 0.4826 (5) | 0.5899 (4) | 0.0723 (16) | |
H10F | 0.5290 | 0.5210 | 0.5457 | 0.087* | |
H10G | 0.5866 | 0.5157 | 0.6358 | 0.087* | |
C105 | 0.5282 (5) | 0.3555 (5) | 0.5703 (3) | 0.0628 (14) | |
C106 | 0.6222 (6) | 0.3101 (5) | 0.6044 (5) | 0.095 (2) | |
H10H | 0.6835 | 0.3594 | 0.6418 | 0.114* | |
C107 | 0.6443 (7) | 0.1867 (5) | 0.5909 (6) | 0.112 (3) | |
H10I | 0.6397 | 0.1511 | 0.6369 | 0.135* | |
H10J | 0.7255 | 0.1837 | 0.5845 | 0.135* | |
C108 | 0.5509 (5) | 0.1187 (4) | 0.5171 (4) | 0.0641 (14) | |
H10K | 0.5732 | 0.1363 | 0.4695 | 0.077* | |
C109 | 0.4247 (4) | 0.1545 (4) | 0.5150 (3) | 0.0492 (11) | |
H10L | 0.4118 | 0.1438 | 0.5665 | 0.059* | |
C110 | 0.4186 (5) | 0.2835 (4) | 0.5095 (3) | 0.0513 (11) | |
C111 | 0.3229 (5) | 0.0730 (4) | 0.4531 (3) | 0.0620 (14) | |
H11C | 0.2450 | 0.0910 | 0.4598 | 0.074* | |
H11D | 0.3259 | 0.0872 | 0.4007 | 0.074* | |
C112 | 0.3303 (5) | −0.0538 (4) | 0.4578 (3) | 0.0573 (13) | |
H11E | 0.3170 | −0.0709 | 0.5075 | 0.069* | |
H11F | 0.2666 | −0.0994 | 0.4151 | 0.069* | |
C113 | 0.4528 (4) | −0.0865 (4) | 0.4521 (3) | 0.0503 (11) | |
C114 | 0.5481 (5) | −0.0098 (4) | 0.5200 (4) | 0.0640 (14) | |
H11G | 0.5263 | −0.0228 | 0.5686 | 0.077* | |
C115 | 0.6670 (6) | −0.0631 (5) | 0.5232 (6) | 0.097 (2) | |
H11H | 0.7073 | −0.0348 | 0.4860 | 0.117* | |
H11I | 0.7223 | −0.0465 | 0.5759 | 0.117* | |
C116 | 0.6227 (7) | −0.1930 (6) | 0.4998 (6) | 0.106 (3) | |
H11J | 0.6525 | −0.2247 | 0.4562 | 0.127* | |
H11K | 0.6517 | −0.2334 | 0.5443 | 0.127* | |
C117 | 0.4828 (5) | −0.2055 (4) | 0.4752 (3) | 0.0604 (13) | |
H11L | 0.4546 | −0.2160 | 0.5220 | 0.072* | |
C118 | 0.4697 (7) | −0.0759 (6) | 0.3711 (4) | 0.0844 (19) | |
H11M | 0.4154 | −0.1346 | 0.3326 | 0.127* | |
H11N | 0.5522 | −0.0848 | 0.3715 | 0.127* | |
H11O | 0.4521 | −0.0017 | 0.3580 | 0.127* | |
C119 | 0.4189 (7) | 0.3091 (5) | 0.4269 (3) | 0.0797 (18) | |
H11P | 0.4841 | 0.2761 | 0.4113 | 0.120* | |
H11Q | 0.4299 | 0.3908 | 0.4276 | 0.120* | |
H11R | 0.3428 | 0.2767 | 0.3900 | 0.120* | |
O120 | 0.3981 (4) | 0.6263 (3) | 0.6193 (2) | 0.0691 (10) | |
C121 | 0.3312 (8) | 0.6673 (6) | 0.6611 (4) | 0.090 (2) | |
O122 | 0.2560 (8) | 0.6054 (5) | 0.6816 (4) | 0.130 (2) | |
C123 | 0.3360 (6) | 0.7938 (4) | 0.6721 (4) | 0.0701 (16) | |
H12C | 0.4188 | 0.8276 | 0.6781 | 0.084* | |
H12D | 0.2847 | 0.8160 | 0.6249 | 0.084* | |
C124 | 0.2966 (8) | 0.8411 (5) | 0.7410 (4) | 0.090 (2) | |
H12E | 0.3495 | 0.8200 | 0.7881 | 0.108* | |
H12F | 0.2150 | 0.8048 | 0.7356 | 0.108* | |
C125 | 0.2964 (6) | 0.9682 (5) | 0.7532 (4) | 0.0663 (14) | |
O126 | 0.3080 (5) | 1.0290 (3) | 0.7052 (3) | 0.0848 (13) | |
O127 | 0.2792 (6) | 1.0076 (4) | 0.8208 (3) | 0.1082 (18) | |
H127 | 0.2739 | 1.0800 | 0.8346 | 0.162* | |
C128 | 0.4260 (6) | −0.3094 (5) | 0.4113 (4) | 0.0697 (15) | |
O129 | 0.4875 (5) | −0.3674 (5) | 0.3810 (4) | 0.132 (2) | |
C130 | 0.2937 (6) | −0.3363 (5) | 0.3882 (4) | 0.0810 (18) | |
H13A | 0.2715 | −0.4160 | 0.3659 | 0.121* | |
H13B | 0.2587 | −0.2895 | 0.3497 | 0.121* | |
H13C | 0.2638 | −0.3212 | 0.4339 | 0.121* | |
C201 | 0.7393 (6) | 0.3831 (5) | 0.3476 (5) | 0.0783 (18) | |
H20A | 0.6549 | 0.3517 | 0.3234 | 0.094* | |
H20B | 0.7654 | 0.3533 | 0.3972 | 0.094* | |
C202 | 0.7467 (6) | 0.5135 (5) | 0.3656 (5) | 0.0846 (19) | |
H20C | 0.7121 | 0.5441 | 0.3175 | 0.101* | |
H20D | 0.7005 | 0.5336 | 0.4031 | 0.101* | |
C203 | 0.8769 (5) | 0.5642 (4) | 0.3996 (3) | 0.0613 (14) | |
H20E | 0.9106 | 0.5351 | 0.4493 | 0.074* | |
C204 | 0.9507 (5) | 0.5339 (4) | 0.3425 (3) | 0.0539 (12) | |
H20F | 1.0348 | 0.5670 | 0.3655 | 0.065* | |
H20G | 0.9196 | 0.5649 | 0.2940 | 0.065* | |
C205 | 0.9428 (4) | 0.4038 (4) | 0.3247 (3) | 0.0473 (11) | |
C206 | 1.0432 (5) | 0.3533 (4) | 0.3400 (3) | 0.0534 (12) | |
H20H | 1.1170 | 0.4001 | 0.3617 | 0.064* | |
C207 | 1.0462 (4) | 0.2275 (4) | 0.3251 (3) | 0.0547 (12) | |
H20I | 1.0637 | 0.1984 | 0.3753 | 0.066* | |
H20J | 1.1116 | 0.2130 | 0.3012 | 0.066* | |
C208 | 0.9276 (4) | 0.1627 (4) | 0.2713 (3) | 0.0430 (10) | |
H20K | 0.9215 | 0.1751 | 0.2167 | 0.052* | |
C209 | 0.8206 (4) | 0.2078 (4) | 0.2965 (3) | 0.0490 (11) | |
H20L | 0.8347 | 0.1995 | 0.3525 | 0.059* | |
C210 | 0.8159 (5) | 0.3391 (4) | 0.2927 (3) | 0.0534 (12) | |
C211 | 0.6975 (5) | 0.1340 (5) | 0.2531 (4) | 0.0728 (17) | |
H21A | 0.6744 | 0.1467 | 0.1984 | 0.087* | |
H21B | 0.6354 | 0.1586 | 0.2774 | 0.087* | |
C212 | 0.7027 (5) | 0.0036 (4) | 0.2557 (4) | 0.0683 (16) | |
H21C | 0.7134 | −0.0108 | 0.3098 | 0.082* | |
H21D | 0.6261 | −0.0390 | 0.2238 | 0.082* | |
C213 | 0.8064 (4) | −0.0390 (4) | 0.2252 (3) | 0.0502 (12) | |
C214 | 0.9241 (4) | 0.0357 (4) | 0.2756 (3) | 0.0428 (10) | |
H21E | 0.9269 | 0.0283 | 0.3307 | 0.051* | |
C215 | 1.0260 (5) | −0.0278 (4) | 0.2577 (4) | 0.0634 (14) | |
H21F | 1.0993 | −0.0102 | 0.3014 | 0.076* | |
H21G | 1.0445 | −0.0078 | 0.2101 | 0.076* | |
C216 | 0.9740 (5) | −0.1557 (5) | 0.2463 (4) | 0.0707 (16) | |
H21H | 0.9838 | −0.1958 | 0.1976 | 0.085* | |
H21I | 1.0162 | −0.1919 | 0.2900 | 0.085* | |
C217 | 0.8397 (5) | −0.1600 (4) | 0.2429 (4) | 0.0611 (13) | |
H21J | 0.8323 | −0.1670 | 0.2962 | 0.073* | |
C218 | 0.7841 (7) | −0.0341 (5) | 0.1377 (4) | 0.0814 (18) | |
H21K | 0.7062 | −0.0759 | 0.1097 | 0.122* | |
H21L | 0.8465 | −0.0679 | 0.1190 | 0.122* | |
H21M | 0.7855 | 0.0445 | 0.1289 | 0.122* | |
C219 | 0.7625 (6) | 0.3604 (5) | 0.2074 (4) | 0.0766 (17) | |
H21N | 0.8101 | 0.3294 | 0.1744 | 0.115* | |
H21O | 0.7639 | 0.4415 | 0.2063 | 0.115* | |
H21P | 0.6801 | 0.3237 | 0.1881 | 0.115* | |
O220 | 0.8801 (4) | 0.6892 (3) | 0.4156 (2) | 0.0672 (10) | |
C221 | 0.9780 (6) | 0.7478 (5) | 0.4683 (3) | 0.0615 (14) | |
O222 | 1.0639 (4) | 0.7066 (3) | 0.5018 (3) | 0.0784 (12) | |
C223 | 0.9667 (6) | 0.8746 (5) | 0.4792 (4) | 0.0777 (18) | |
H22A | 1.0032 | 0.9107 | 0.4429 | 0.093* | |
H22B | 0.8812 | 0.8846 | 0.4655 | 0.093* | |
C224 | 1.0240 (7) | 0.9330 (5) | 0.5593 (4) | 0.0782 (18) | |
H22C | 1.1102 | 0.9261 | 0.5722 | 0.094* | |
H22D | 0.9900 | 0.8948 | 0.5958 | 0.094* | |
C225 | 1.0080 (6) | 1.0568 (5) | 0.5708 (3) | 0.0670 (15) | |
O226 | 0.9956 (7) | 1.1142 (4) | 0.5189 (3) | 0.1100 (19) | |
O227 | 1.0057 (6) | 1.0975 (4) | 0.6405 (3) | 0.1071 (18) | |
H227 | 0.9991 | 1.1751 | 0.6552 | 0.161* | |
C228 | 0.7618 (6) | −0.2613 (6) | 0.1877 (6) | 0.094 (2) | |
O229 | 0.7984 (6) | −0.3193 (5) | 0.1432 (5) | 0.153 (3) | |
C230 | 0.6325 (8) | −0.2836 (7) | 0.1951 (8) | 0.149 (5) | |
H23C | 0.6003 | −0.3624 | 0.1745 | 0.224* | |
H23D | 0.5825 | −0.2342 | 0.1656 | 0.224* | |
H23E | 0.6332 | −0.2683 | 0.2498 | 0.224* | |
C301 | 0.1501 (5) | −0.0855 (4) | 0.0273 (4) | 0.0671 (15) | |
H30D | 0.1140 | −0.0575 | −0.0217 | 0.081* | |
H30E | 0.0928 | −0.0817 | 0.0591 | 0.081* | |
C302 | 0.1682 (7) | −0.2114 (5) | 0.0077 (4) | 0.0809 (19) | |
H30F | 0.1936 | −0.2436 | 0.0564 | 0.097* | |
H30G | 0.0916 | −0.2548 | −0.0236 | 0.097* | |
C303 | 0.2607 (7) | −0.2223 (5) | −0.0366 (4) | 0.084 (2) | |
H30H | 0.2337 | −0.1941 | −0.0873 | 0.100* | |
C304 | 0.3819 (6) | −0.1557 (5) | 0.0113 (4) | 0.0791 (18) | |
H30I | 0.4119 | −0.1888 | 0.0592 | 0.095* | |
H30J | 0.4408 | −0.1611 | −0.0193 | 0.095* | |
C305 | 0.3677 (5) | −0.0305 (5) | 0.0331 (3) | 0.0573 (14) | |
C306 | 0.4430 (5) | 0.0509 (5) | 0.0191 (3) | 0.0636 (14) | |
H30K | 0.5015 | 0.0275 | −0.0053 | 0.076* | |
C307 | 0.4423 (5) | 0.1746 (5) | 0.0387 (3) | 0.0612 (14) | |
H30L | 0.4161 | 0.2066 | −0.0100 | 0.073* | |
H30M | 0.5247 | 0.2100 | 0.0653 | 0.073* | |
C308 | 0.3594 (4) | 0.2057 (4) | 0.0915 (3) | 0.0458 (11) | |
H30N | 0.4022 | 0.2011 | 0.1465 | 0.055* | |
C309 | 0.2423 (4) | 0.1197 (4) | 0.0666 (3) | 0.0456 (10) | |
H30O | 0.2061 | 0.1231 | 0.0104 | 0.055* | |
C310 | 0.2664 (4) | −0.0054 (4) | 0.0715 (3) | 0.0485 (11) | |
C311 | 0.1486 (5) | 0.1575 (4) | 0.1095 (4) | 0.0574 (13) | |
H31A | 0.0728 | 0.1069 | 0.0870 | 0.069* | |
H31B | 0.1774 | 0.1486 | 0.1648 | 0.069* | |
C312 | 0.1234 (5) | 0.2813 (4) | 0.1046 (3) | 0.0569 (12) | |
H31C | 0.0833 | 0.2883 | 0.0503 | 0.068* | |
H31D | 0.0689 | 0.3008 | 0.1367 | 0.068* | |
C313 | 0.2394 (4) | 0.3647 (4) | 0.1331 (3) | 0.0482 (11) | |
C314 | 0.3268 (4) | 0.3267 (4) | 0.0861 (3) | 0.0487 (11) | |
H31E | 0.2837 | 0.3263 | 0.0305 | 0.058* | |
C315 | 0.4297 (5) | 0.4276 (5) | 0.1065 (4) | 0.0670 (15) | |
H31F | 0.4910 | 0.4213 | 0.1546 | 0.080* | |
H31G | 0.4679 | 0.4310 | 0.0637 | 0.080* | |
C316 | 0.3640 (5) | 0.5328 (5) | 0.1177 (4) | 0.0700 (16) | |
H31H | 0.4027 | 0.5785 | 0.1689 | 0.084* | |
H31I | 0.3674 | 0.5802 | 0.0770 | 0.084* | |
C317 | 0.2325 (5) | 0.4904 (4) | 0.1124 (3) | 0.0548 (12) | |
H31J | 0.1864 | 0.4835 | 0.0567 | 0.066* | |
C318 | 0.2923 (6) | 0.3709 (5) | 0.2226 (3) | 0.0641 (14) | |
H31K | 0.3093 | 0.2960 | 0.2346 | 0.096* | |
H31L | 0.2347 | 0.3973 | 0.2493 | 0.096* | |
H31M | 0.3662 | 0.4234 | 0.2399 | 0.096* | |
C319 | 0.3065 (6) | −0.0300 (5) | 0.1578 (3) | 0.0677 (15) | |
H31N | 0.3796 | 0.0196 | 0.1860 | 0.102* | |
H31O | 0.3213 | −0.1087 | 0.1577 | 0.102* | |
H31P | 0.2434 | −0.0163 | 0.1831 | 0.102* | |
O320 | 0.2853 (6) | −0.3420 (4) | −0.0499 (2) | 0.1014 (18) | |
C321 | 0.2294 (6) | −0.4072 (5) | −0.1147 (4) | 0.0652 (14) | |
O322 | 0.1502 (6) | −0.3744 (4) | −0.1636 (3) | 0.117 (2) | |
C323 | 0.2577 (6) | −0.5258 (4) | −0.1201 (4) | 0.0670 (15) | |
H32A | 0.2041 | −0.5705 | −0.0973 | 0.080* | |
H32B | 0.3404 | −0.5261 | −0.0884 | 0.080* | |
C324 | 0.2461 (8) | −0.5829 (5) | −0.2011 (4) | 0.087 (2) | |
H32C | 0.3046 | −0.5413 | −0.2221 | 0.105* | |
H32D | 0.1657 | −0.5762 | −0.2338 | 0.105* | |
C325 | 0.2645 (5) | −0.7061 (5) | −0.2095 (3) | 0.0595 (13) | |
O326 | 0.2692 (4) | −0.7646 (3) | −0.1583 (2) | 0.0737 (11) | |
O327 | 0.2751 (6) | −0.7463 (3) | −0.2792 (3) | 0.0997 (17) | |
H327 | 0.2932 | −0.8307 | −0.2855 | 0.150* | |
C328 | 0.1731 (6) | 0.5703 (5) | 0.1595 (3) | 0.0677 (15) | |
O329 | 0.2282 (6) | 0.6605 (4) | 0.1963 (3) | 0.1094 (17) | |
C330 | 0.0441 (8) | 0.5409 (6) | 0.1571 (5) | 0.101 (2) | |
H33A | 0.0012 | 0.6056 | 0.1459 | 0.151* | |
H33B | 0.0389 | 0.5214 | 0.2074 | 0.151* | |
H33C | 0.0085 | 0.4765 | 0.1166 | 0.151* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.093 (6) | 0.070 (5) | 0.211 (10) | 0.011 (4) | −0.006 (6) | −0.057 (6) |
C2 | 0.099 (6) | 0.075 (5) | 0.173 (8) | 0.013 (4) | 0.018 (6) | −0.045 (5) |
C3 | 0.132 (6) | 0.052 (4) | 0.074 (4) | 0.030 (4) | 0.025 (4) | −0.004 (3) |
C4 | 0.089 (4) | 0.060 (4) | 0.097 (5) | 0.024 (3) | 0.022 (4) | 0.017 (3) |
C5 | 0.070 (4) | 0.063 (3) | 0.064 (3) | 0.018 (3) | 0.024 (3) | 0.013 (3) |
C6 | 0.066 (4) | 0.072 (4) | 0.113 (5) | 0.023 (3) | 0.044 (4) | 0.011 (3) |
C7 | 0.065 (4) | 0.064 (4) | 0.098 (4) | 0.013 (3) | 0.041 (3) | 0.017 (3) |
C8 | 0.049 (3) | 0.050 (3) | 0.058 (3) | 0.004 (2) | 0.017 (2) | 0.003 (2) |
C9 | 0.055 (3) | 0.064 (4) | 0.103 (5) | 0.009 (3) | 0.018 (3) | −0.019 (3) |
C10 | 0.073 (4) | 0.062 (4) | 0.098 (5) | 0.009 (3) | 0.028 (3) | −0.013 (3) |
C11 | 0.049 (4) | 0.085 (5) | 0.308 (14) | −0.014 (4) | 0.035 (6) | −0.088 (7) |
C12 | 0.052 (4) | 0.095 (6) | 0.294 (13) | 0.019 (4) | −0.008 (6) | −0.090 (7) |
C13 | 0.051 (3) | 0.064 (4) | 0.152 (7) | 0.006 (3) | 0.033 (4) | −0.027 (4) |
C14 | 0.048 (3) | 0.060 (3) | 0.061 (3) | 0.007 (2) | 0.014 (2) | 0.002 (2) |
C15 | 0.052 (3) | 0.059 (3) | 0.095 (4) | 0.004 (3) | 0.027 (3) | 0.012 (3) |
C16 | 0.073 (4) | 0.061 (4) | 0.095 (4) | 0.003 (3) | 0.018 (3) | 0.000 (3) |
C17 | 0.067 (4) | 0.069 (4) | 0.146 (7) | 0.023 (3) | 0.008 (4) | −0.022 (4) |
C18 | 0.150 (8) | 0.102 (6) | 0.193 (10) | −0.009 (5) | 0.138 (8) | −0.017 (6) |
C19 | 0.197 (10) | 0.080 (5) | 0.147 (8) | −0.005 (6) | 0.123 (8) | −0.003 (5) |
O20 | 0.146 (4) | 0.064 (3) | 0.081 (3) | 0.041 (3) | 0.046 (3) | 0.013 (2) |
C21 | 0.092 (4) | 0.054 (3) | 0.080 (4) | 0.019 (3) | 0.033 (3) | 0.015 (3) |
O22 | 0.404 (14) | 0.086 (4) | 0.249 (9) | 0.127 (6) | 0.255 (10) | 0.092 (5) |
C23 | 0.092 (4) | 0.047 (3) | 0.063 (3) | 0.013 (3) | 0.022 (3) | 0.001 (2) |
C24 | 0.159 (7) | 0.061 (4) | 0.093 (5) | 0.039 (4) | 0.071 (5) | 0.018 (3) |
C25 | 0.098 (4) | 0.051 (3) | 0.060 (3) | 0.018 (3) | 0.021 (3) | 0.009 (3) |
O26 | 0.135 (4) | 0.058 (2) | 0.069 (3) | 0.028 (2) | 0.026 (3) | 0.004 (2) |
O27 | 0.253 (8) | 0.071 (3) | 0.097 (4) | 0.054 (4) | 0.092 (5) | 0.021 (3) |
C28 | 0.077 (5) | 0.076 (5) | 0.280 (14) | 0.023 (4) | 0.023 (7) | −0.044 (7) |
O29 | 0.160 (8) | 0.240 (11) | 0.246 (11) | 0.067 (8) | 0.046 (7) | −0.074 (9) |
C30 | 0.076 (6) | 0.114 (7) | 0.195 (10) | 0.031 (5) | 0.013 (6) | −0.013 (7) |
C101 | 0.055 (3) | 0.051 (3) | 0.067 (3) | 0.013 (2) | 0.005 (3) | −0.002 (2) |
C102 | 0.074 (4) | 0.052 (3) | 0.085 (4) | 0.022 (3) | 0.013 (3) | −0.001 (3) |
C103 | 0.086 (4) | 0.038 (3) | 0.058 (3) | 0.015 (3) | 0.016 (3) | 0.002 (2) |
C104 | 0.075 (4) | 0.042 (3) | 0.088 (4) | 0.006 (3) | 0.007 (3) | −0.004 (3) |
C105 | 0.061 (3) | 0.047 (3) | 0.075 (4) | 0.014 (3) | 0.009 (3) | 0.004 (3) |
C106 | 0.063 (4) | 0.051 (3) | 0.137 (6) | 0.003 (3) | −0.018 (4) | −0.017 (4) |
C107 | 0.077 (4) | 0.045 (3) | 0.167 (7) | 0.010 (3) | −0.037 (5) | −0.017 (4) |
C108 | 0.050 (3) | 0.042 (3) | 0.092 (4) | 0.006 (2) | 0.009 (3) | 0.002 (3) |
C109 | 0.053 (3) | 0.041 (2) | 0.051 (3) | 0.011 (2) | 0.006 (2) | 0.005 (2) |
C110 | 0.058 (3) | 0.043 (3) | 0.050 (3) | 0.008 (2) | 0.012 (2) | 0.002 (2) |
C111 | 0.057 (3) | 0.052 (3) | 0.070 (3) | 0.013 (2) | 0.006 (3) | 0.002 (2) |
C112 | 0.052 (3) | 0.045 (3) | 0.071 (3) | 0.008 (2) | 0.011 (3) | 0.002 (2) |
C113 | 0.051 (3) | 0.041 (3) | 0.063 (3) | 0.008 (2) | 0.022 (2) | 0.008 (2) |
C114 | 0.052 (3) | 0.049 (3) | 0.087 (4) | 0.017 (2) | 0.009 (3) | 0.006 (3) |
C115 | 0.057 (4) | 0.053 (3) | 0.170 (7) | 0.021 (3) | 0.011 (4) | 0.000 (4) |
C116 | 0.075 (4) | 0.059 (4) | 0.164 (7) | 0.023 (3) | −0.001 (4) | −0.006 (4) |
C117 | 0.063 (3) | 0.042 (3) | 0.074 (3) | 0.012 (2) | 0.014 (3) | 0.003 (2) |
C118 | 0.121 (6) | 0.060 (4) | 0.091 (4) | 0.018 (4) | 0.055 (4) | 0.020 (3) |
C119 | 0.137 (6) | 0.045 (3) | 0.064 (3) | 0.022 (3) | 0.032 (4) | 0.017 (3) |
O120 | 0.099 (3) | 0.0391 (19) | 0.075 (2) | 0.0168 (19) | 0.035 (2) | 0.0010 (17) |
C121 | 0.150 (7) | 0.053 (4) | 0.087 (4) | 0.013 (4) | 0.065 (5) | 0.021 (3) |
O122 | 0.196 (7) | 0.075 (3) | 0.153 (5) | 0.026 (4) | 0.104 (5) | 0.024 (3) |
C123 | 0.099 (4) | 0.043 (3) | 0.074 (4) | 0.024 (3) | 0.030 (3) | 0.005 (3) |
C124 | 0.150 (7) | 0.050 (3) | 0.096 (5) | 0.028 (4) | 0.070 (5) | 0.017 (3) |
C125 | 0.087 (4) | 0.049 (3) | 0.066 (4) | 0.016 (3) | 0.030 (3) | −0.001 (3) |
O126 | 0.144 (4) | 0.045 (2) | 0.077 (3) | 0.023 (2) | 0.050 (3) | 0.005 (2) |
O127 | 0.200 (6) | 0.060 (3) | 0.087 (3) | 0.041 (3) | 0.071 (4) | 0.010 (2) |
C128 | 0.078 (4) | 0.045 (3) | 0.088 (4) | 0.015 (3) | 0.028 (3) | 0.001 (3) |
O129 | 0.100 (4) | 0.089 (4) | 0.191 (6) | 0.030 (3) | 0.036 (4) | −0.054 (4) |
C130 | 0.089 (5) | 0.052 (3) | 0.094 (4) | 0.001 (3) | 0.021 (4) | −0.003 (3) |
C201 | 0.059 (4) | 0.055 (3) | 0.128 (6) | 0.017 (3) | 0.042 (4) | 0.001 (3) |
C202 | 0.080 (4) | 0.058 (4) | 0.122 (5) | 0.026 (3) | 0.042 (4) | −0.007 (3) |
C203 | 0.074 (4) | 0.042 (3) | 0.069 (3) | 0.021 (3) | 0.023 (3) | −0.003 (2) |
C204 | 0.055 (3) | 0.041 (3) | 0.066 (3) | 0.009 (2) | 0.019 (2) | 0.001 (2) |
C205 | 0.051 (3) | 0.042 (3) | 0.047 (3) | 0.007 (2) | 0.010 (2) | 0.0046 (19) |
C206 | 0.046 (3) | 0.046 (3) | 0.063 (3) | 0.007 (2) | 0.010 (2) | −0.001 (2) |
C207 | 0.036 (3) | 0.046 (3) | 0.078 (3) | 0.005 (2) | 0.011 (2) | 0.001 (2) |
C208 | 0.037 (2) | 0.039 (2) | 0.050 (2) | 0.0014 (18) | 0.007 (2) | 0.0072 (19) |
C209 | 0.043 (3) | 0.042 (3) | 0.062 (3) | 0.009 (2) | 0.015 (2) | 0.004 (2) |
C210 | 0.050 (3) | 0.039 (2) | 0.067 (3) | 0.013 (2) | 0.008 (2) | 0.001 (2) |
C211 | 0.044 (3) | 0.050 (3) | 0.119 (5) | 0.008 (2) | 0.017 (3) | 0.001 (3) |
C212 | 0.036 (3) | 0.049 (3) | 0.113 (5) | −0.005 (2) | 0.016 (3) | 0.006 (3) |
C213 | 0.045 (3) | 0.038 (3) | 0.061 (3) | −0.001 (2) | 0.004 (2) | 0.006 (2) |
C214 | 0.038 (2) | 0.038 (2) | 0.050 (3) | 0.0051 (19) | 0.009 (2) | 0.0064 (19) |
C215 | 0.046 (3) | 0.046 (3) | 0.100 (4) | 0.012 (2) | 0.022 (3) | 0.006 (3) |
C216 | 0.059 (3) | 0.043 (3) | 0.104 (5) | 0.010 (2) | 0.014 (3) | 0.004 (3) |
C217 | 0.057 (3) | 0.039 (3) | 0.080 (3) | 0.004 (2) | 0.006 (3) | 0.007 (2) |
C218 | 0.090 (4) | 0.049 (3) | 0.080 (4) | 0.005 (3) | −0.015 (3) | −0.004 (3) |
C219 | 0.076 (4) | 0.055 (3) | 0.082 (4) | 0.015 (3) | −0.011 (3) | 0.012 (3) |
O220 | 0.073 (2) | 0.046 (2) | 0.079 (3) | 0.0235 (18) | 0.016 (2) | −0.0086 (18) |
C221 | 0.073 (4) | 0.051 (3) | 0.060 (3) | 0.022 (3) | 0.018 (3) | −0.006 (3) |
O222 | 0.088 (3) | 0.058 (2) | 0.081 (3) | 0.026 (2) | 0.012 (2) | −0.009 (2) |
C223 | 0.090 (4) | 0.046 (3) | 0.087 (4) | 0.023 (3) | 0.009 (3) | −0.004 (3) |
C224 | 0.117 (5) | 0.045 (3) | 0.067 (3) | 0.017 (3) | 0.015 (3) | 0.004 (3) |
C225 | 0.087 (4) | 0.050 (3) | 0.058 (3) | 0.010 (3) | 0.013 (3) | −0.005 (3) |
O226 | 0.216 (6) | 0.053 (3) | 0.078 (3) | 0.039 (3) | 0.063 (4) | 0.009 (2) |
O227 | 0.197 (6) | 0.061 (3) | 0.067 (3) | 0.038 (3) | 0.038 (3) | 0.001 (2) |
C228 | 0.063 (4) | 0.044 (3) | 0.157 (7) | 0.005 (3) | −0.005 (4) | 0.015 (4) |
O229 | 0.108 (5) | 0.087 (4) | 0.206 (7) | 0.026 (3) | −0.021 (4) | −0.073 (4) |
C230 | 0.079 (5) | 0.073 (5) | 0.265 (14) | −0.024 (4) | 0.009 (7) | 0.013 (7) |
C301 | 0.063 (3) | 0.046 (3) | 0.082 (4) | 0.010 (3) | 0.008 (3) | −0.006 (3) |
C302 | 0.094 (5) | 0.045 (3) | 0.091 (4) | 0.014 (3) | 0.006 (4) | 0.001 (3) |
C303 | 0.136 (6) | 0.049 (3) | 0.066 (4) | 0.046 (4) | 0.018 (4) | 0.005 (3) |
C304 | 0.093 (5) | 0.064 (4) | 0.081 (4) | 0.039 (3) | 0.020 (4) | −0.001 (3) |
C305 | 0.064 (3) | 0.056 (3) | 0.048 (3) | 0.027 (3) | 0.005 (2) | −0.002 (2) |
C306 | 0.061 (3) | 0.075 (4) | 0.065 (3) | 0.023 (3) | 0.032 (3) | 0.008 (3) |
C307 | 0.053 (3) | 0.074 (4) | 0.066 (3) | 0.016 (3) | 0.026 (3) | 0.019 (3) |
C308 | 0.041 (2) | 0.052 (3) | 0.046 (2) | 0.009 (2) | 0.012 (2) | 0.009 (2) |
C309 | 0.042 (2) | 0.045 (3) | 0.051 (3) | 0.009 (2) | 0.014 (2) | 0.004 (2) |
C310 | 0.051 (3) | 0.044 (3) | 0.051 (3) | 0.013 (2) | 0.013 (2) | 0.004 (2) |
C311 | 0.056 (3) | 0.037 (3) | 0.084 (4) | 0.002 (2) | 0.032 (3) | 0.002 (2) |
C312 | 0.051 (3) | 0.051 (3) | 0.072 (3) | 0.004 (2) | 0.025 (3) | 0.004 (2) |
C313 | 0.053 (3) | 0.040 (2) | 0.050 (3) | 0.008 (2) | 0.011 (2) | 0.002 (2) |
C314 | 0.045 (3) | 0.049 (3) | 0.050 (3) | 0.000 (2) | 0.008 (2) | 0.012 (2) |
C315 | 0.059 (3) | 0.057 (3) | 0.082 (4) | −0.002 (3) | 0.015 (3) | 0.016 (3) |
C316 | 0.067 (4) | 0.048 (3) | 0.088 (4) | −0.003 (3) | 0.006 (3) | 0.021 (3) |
C317 | 0.063 (3) | 0.047 (3) | 0.051 (3) | 0.006 (2) | 0.008 (2) | 0.014 (2) |
C318 | 0.089 (4) | 0.052 (3) | 0.051 (3) | 0.016 (3) | 0.015 (3) | 0.008 (2) |
C319 | 0.098 (4) | 0.048 (3) | 0.061 (3) | 0.022 (3) | 0.024 (3) | 0.008 (2) |
O320 | 0.178 (5) | 0.054 (2) | 0.062 (2) | 0.052 (3) | 0.008 (3) | −0.007 (2) |
C321 | 0.080 (4) | 0.052 (3) | 0.064 (3) | 0.011 (3) | 0.018 (3) | 0.009 (3) |
O322 | 0.145 (5) | 0.072 (3) | 0.103 (4) | 0.033 (3) | −0.015 (4) | −0.013 (3) |
C323 | 0.078 (4) | 0.043 (3) | 0.075 (4) | 0.011 (3) | 0.016 (3) | −0.003 (2) |
C324 | 0.152 (6) | 0.044 (3) | 0.062 (3) | 0.020 (4) | 0.020 (4) | 0.001 (3) |
C325 | 0.067 (3) | 0.046 (3) | 0.059 (3) | 0.008 (2) | 0.010 (3) | −0.006 (3) |
O326 | 0.113 (3) | 0.047 (2) | 0.065 (2) | 0.020 (2) | 0.029 (2) | 0.0045 (19) |
O327 | 0.193 (6) | 0.050 (2) | 0.065 (3) | 0.029 (3) | 0.047 (3) | 0.0053 (19) |
C328 | 0.100 (5) | 0.038 (3) | 0.064 (3) | 0.019 (3) | 0.016 (3) | 0.007 (2) |
O329 | 0.155 (5) | 0.055 (3) | 0.108 (4) | 0.007 (3) | 0.029 (3) | −0.011 (2) |
C330 | 0.120 (6) | 0.076 (4) | 0.123 (6) | 0.040 (4) | 0.056 (5) | 0.007 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.537 (11) | C201—C202 | 1.525 (8) |
C1—C10 | 1.562 (10) | C201—C210 | 1.545 (8) |
C1—H1A | 0.9700 | C201—H20A | 0.9700 |
C1—H1B | 0.9700 | C201—H20B | 0.9700 |
C2—C3 | 1.484 (12) | C202—C203 | 1.497 (9) |
C2—H2A | 0.9700 | C202—H20C | 0.9700 |
C2—H2B | 0.9700 | C202—H20D | 0.9700 |
C3—O20 | 1.463 (7) | C203—O220 | 1.465 (6) |
C3—C4 | 1.513 (10) | C203—C204 | 1.507 (7) |
C3—H3A | 0.9800 | C203—H20E | 0.9800 |
C4—C5 | 1.525 (8) | C204—C205 | 1.522 (6) |
C4—H4A | 0.9700 | C204—H20F | 0.9700 |
C4—H4B | 0.9700 | C204—H20G | 0.9700 |
C5—C6 | 1.299 (9) | C205—C206 | 1.327 (7) |
C5—C10 | 1.497 (9) | C205—C210 | 1.514 (7) |
C6—C7 | 1.483 (9) | C206—C207 | 1.483 (7) |
C6—H6A | 0.9300 | C206—H20H | 0.9300 |
C7—C8 | 1.506 (8) | C207—C208 | 1.520 (7) |
C7—H7A | 0.9700 | C207—H20I | 0.9700 |
C7—H7B | 0.9700 | C207—H20J | 0.9700 |
C8—C14 | 1.520 (7) | C208—C214 | 1.509 (6) |
C8—C9 | 1.529 (8) | C208—C209 | 1.526 (6) |
C8—H8A | 0.9800 | C208—H20K | 0.9800 |
C9—C11 | 1.527 (10) | C209—C211 | 1.549 (7) |
C9—C10 | 1.553 (9) | C209—C210 | 1.567 (6) |
C9—H9A | 0.9800 | C209—H20L | 0.9800 |
C10—C19 | 1.565 (11) | C210—C219 | 1.536 (8) |
C11—C12 | 1.574 (13) | C211—C212 | 1.552 (7) |
C11—H11A | 0.9700 | C211—H21A | 0.9700 |
C11—H11B | 0.9700 | C211—H21B | 0.9700 |
C12—C13 | 1.520 (10) | C212—C213 | 1.529 (8) |
C12—H12A | 0.9700 | C212—H21C | 0.9700 |
C12—H12B | 0.9700 | C212—H21D | 0.9700 |
C13—C14 | 1.514 (8) | C213—C218 | 1.510 (8) |
C13—C17 | 1.541 (10) | C213—C214 | 1.540 (6) |
C13—C18 | 1.579 (14) | C213—C217 | 1.559 (7) |
C14—C15 | 1.519 (8) | C214—C215 | 1.524 (7) |
C14—H14A | 0.9800 | C214—H21E | 0.9800 |
C15—C16 | 1.535 (9) | C215—C216 | 1.543 (8) |
C15—H15A | 0.9700 | C215—H21F | 0.9700 |
C15—H15B | 0.9700 | C215—H21G | 0.9700 |
C16—C17 | 1.540 (10) | C216—C217 | 1.522 (8) |
C16—H16A | 0.9700 | C216—H21H | 0.9700 |
C16—H16B | 0.9700 | C216—H21I | 0.9700 |
C17—C28 | 1.456 (11) | C217—C228 | 1.503 (9) |
C17—H17A | 0.9800 | C217—H21J | 0.9800 |
C18—H18A | 0.9600 | C218—H21K | 0.9600 |
C18—H18B | 0.9600 | C218—H21L | 0.9600 |
C18—H18C | 0.9600 | C218—H21M | 0.9600 |
C19—H19A | 0.9600 | C219—H21N | 0.9600 |
C19—H19B | 0.9600 | C219—H21O | 0.9600 |
C19—H19C | 0.9600 | C219—H21P | 0.9600 |
O20—C21 | 1.316 (8) | O220—C221 | 1.332 (7) |
C21—O22 | 1.150 (8) | C221—O222 | 1.190 (7) |
C21—C23 | 1.470 (8) | C221—C223 | 1.509 (7) |
C23—C24 | 1.498 (8) | C223—C224 | 1.454 (9) |
C23—H23A | 0.9700 | C223—H22A | 0.9700 |
C23—H23B | 0.9700 | C223—H22B | 0.9700 |
C24—C25 | 1.462 (8) | C224—C225 | 1.488 (8) |
C24—H24A | 0.9700 | C224—H22C | 0.9700 |
C24—H24B | 0.9700 | C224—H22D | 0.9700 |
C25—O26 | 1.197 (7) | C225—O226 | 1.193 (7) |
C25—O27 | 1.282 (7) | C225—O227 | 1.275 (7) |
O27—H27 | 0.8873 | O227—H227 | 0.9382 |
C28—O29 | 1.356 (14) | C228—O229 | 1.164 (10) |
C28—C30 | 1.369 (15) | C228—C230 | 1.524 (12) |
C30—H30A | 0.9600 | C230—H23C | 0.9600 |
C30—H30B | 0.9600 | C230—H23D | 0.9600 |
C30—H30C | 0.9600 | C230—H23E | 0.9600 |
C101—C102 | 1.519 (7) | C301—C310 | 1.531 (7) |
C101—C110 | 1.537 (7) | C301—C302 | 1.532 (8) |
C101—H10A | 0.9700 | C301—H30D | 0.9700 |
C101—H10B | 0.9700 | C301—H30E | 0.9700 |
C102—C103 | 1.493 (8) | C302—C303 | 1.478 (10) |
C102—H10C | 0.9700 | C302—H30F | 0.9700 |
C102—H10D | 0.9700 | C302—H30G | 0.9700 |
C103—O120 | 1.464 (6) | C303—O320 | 1.470 (6) |
C103—C104 | 1.516 (9) | C303—C304 | 1.518 (10) |
C103—H10E | 0.9800 | C303—H30H | 0.9800 |
C104—C105 | 1.515 (7) | C304—C305 | 1.517 (7) |
C104—H10F | 0.9700 | C304—H30I | 0.9700 |
C104—H10G | 0.9700 | C304—H30J | 0.9700 |
C105—C106 | 1.290 (8) | C305—C306 | 1.322 (8) |
C105—C110 | 1.533 (8) | C305—C310 | 1.522 (7) |
C106—C107 | 1.504 (9) | C306—C307 | 1.462 (8) |
C106—H10H | 0.9300 | C306—H30K | 0.9300 |
C107—C108 | 1.538 (9) | C307—C308 | 1.533 (7) |
C107—H10I | 0.9700 | C307—H30L | 0.9700 |
C107—H10J | 0.9700 | C307—H30M | 0.9700 |
C108—C114 | 1.524 (7) | C308—C314 | 1.519 (7) |
C108—C109 | 1.537 (7) | C308—C309 | 1.539 (7) |
C108—H10K | 0.9800 | C308—H30N | 0.9800 |
C109—C111 | 1.541 (7) | C309—C311 | 1.535 (7) |
C109—C110 | 1.545 (7) | C309—C310 | 1.537 (6) |
C109—H10L | 0.9800 | C309—H30O | 0.9800 |
C110—C119 | 1.527 (8) | C310—C319 | 1.548 (7) |
C111—C112 | 1.519 (7) | C311—C312 | 1.524 (7) |
C111—H11C | 0.9700 | C311—H31A | 0.9700 |
C111—H11D | 0.9700 | C311—H31B | 0.9700 |
C112—C113 | 1.515 (7) | C312—C313 | 1.515 (7) |
C112—H11E | 0.9700 | C312—H31C | 0.9700 |
C112—H11F | 0.9700 | C312—H31D | 0.9700 |
C113—C118 | 1.512 (8) | C313—C314 | 1.522 (7) |
C113—C114 | 1.529 (8) | C313—C318 | 1.532 (7) |
C113—C117 | 1.554 (7) | C313—C317 | 1.576 (7) |
C114—C115 | 1.544 (8) | C314—C315 | 1.538 (7) |
C114—H11G | 0.9800 | C314—H31E | 0.9800 |
C115—C116 | 1.544 (10) | C315—C316 | 1.529 (8) |
C115—H11H | 0.9700 | C315—H31F | 0.9700 |
C115—H11I | 0.9700 | C315—H31G | 0.9700 |
C116—C117 | 1.539 (9) | C316—C317 | 1.521 (8) |
C116—H11J | 0.9700 | C316—H31H | 0.9700 |
C116—H11K | 0.9700 | C316—H31I | 0.9700 |
C117—C128 | 1.533 (8) | C317—C328 | 1.506 (8) |
C117—H11L | 0.9800 | C317—H31J | 0.9800 |
C118—H11M | 0.9600 | C318—H31K | 0.9600 |
C118—H11N | 0.9600 | C318—H31L | 0.9600 |
C118—H11O | 0.9600 | C318—H31M | 0.9600 |
C119—H11P | 0.9600 | C319—H31N | 0.9600 |
C119—H11Q | 0.9600 | C319—H31O | 0.9600 |
C119—H11R | 0.9600 | C319—H31P | 0.9600 |
O120—C121 | 1.281 (8) | O320—C321 | 1.281 (7) |
C121—O122 | 1.233 (9) | C321—O322 | 1.210 (7) |
C121—C123 | 1.478 (8) | C321—C323 | 1.464 (8) |
C123—C124 | 1.472 (9) | C323—C324 | 1.476 (8) |
C123—H12C | 0.9700 | C323—H32A | 0.9700 |
C123—H12D | 0.9700 | C323—H32B | 0.9700 |
C124—C125 | 1.492 (8) | C324—C325 | 1.486 (8) |
C124—H12E | 0.9700 | C324—H32C | 0.9700 |
C124—H12F | 0.9700 | C324—H32D | 0.9700 |
C125—O126 | 1.201 (7) | C325—O326 | 1.197 (7) |
C125—O127 | 1.299 (7) | C325—O327 | 1.307 (7) |
O127—H127 | 0.8727 | O327—H327 | 1.0366 |
C128—O129 | 1.203 (7) | C328—O329 | 1.208 (7) |
C128—C130 | 1.461 (9) | C328—C330 | 1.478 (11) |
C130—H13A | 0.9600 | C330—H33A | 0.9600 |
C130—H13B | 0.9600 | C330—H33B | 0.9600 |
C130—H13C | 0.9600 | C330—H33C | 0.9600 |
| | | |
C2—C1—C10 | 114.1 (7) | C202—C201—C210 | 115.2 (5) |
C2—C1—H1A | 108.7 | C202—C201—H20A | 108.5 |
C10—C1—H1A | 108.7 | C210—C201—H20A | 108.5 |
C2—C1—H1B | 108.7 | C202—C201—H20B | 108.5 |
C10—C1—H1B | 108.7 | C210—C201—H20B | 108.5 |
H1A—C1—H1B | 107.6 | H20A—C201—H20B | 107.5 |
C3—C2—C1 | 109.4 (8) | C203—C202—C201 | 109.4 (5) |
C3—C2—H2A | 109.8 | C203—C202—H20C | 109.8 |
C1—C2—H2A | 109.8 | C201—C202—H20C | 109.8 |
C3—C2—H2B | 109.8 | C203—C202—H20D | 109.8 |
C1—C2—H2B | 109.8 | C201—C202—H20D | 109.8 |
H2A—C2—H2B | 108.2 | H20C—C202—H20D | 108.2 |
O20—C3—C2 | 106.8 (6) | O220—C203—C202 | 107.7 (4) |
O20—C3—C4 | 108.1 (5) | O220—C203—C204 | 110.0 (4) |
C2—C3—C4 | 110.7 (6) | C202—C203—C204 | 110.8 (5) |
O20—C3—H3A | 110.4 | O220—C203—H20E | 109.4 |
C2—C3—H3A | 110.4 | C202—C203—H20E | 109.4 |
C4—C3—H3A | 110.4 | C204—C203—H20E | 109.4 |
C3—C4—C5 | 110.2 (5) | C203—C204—C205 | 109.2 (4) |
C3—C4—H4A | 109.6 | C203—C204—H20F | 109.8 |
C5—C4—H4A | 109.6 | C205—C204—H20F | 109.8 |
C3—C4—H4B | 109.6 | C203—C204—H20G | 109.8 |
C5—C4—H4B | 109.6 | C205—C204—H20G | 109.8 |
H4A—C4—H4B | 108.1 | H20F—C204—H20G | 108.3 |
C6—C5—C10 | 122.4 (6) | C206—C205—C210 | 123.9 (4) |
C6—C5—C4 | 120.7 (6) | C206—C205—C204 | 120.0 (5) |
C10—C5—C4 | 116.9 (6) | C210—C205—C204 | 116.0 (4) |
C5—C6—C7 | 126.1 (6) | C205—C206—C207 | 124.6 (5) |
C5—C6—H6A | 116.9 | C205—C206—H20H | 117.7 |
C7—C6—H6A | 116.9 | C207—C206—H20H | 117.7 |
C6—C7—C8 | 113.2 (5) | C206—C207—C208 | 113.1 (4) |
C6—C7—H7A | 108.9 | C206—C207—H20I | 109.0 |
C8—C7—H7A | 108.9 | C208—C207—H20I | 109.0 |
C6—C7—H7B | 108.9 | C206—C207—H20J | 109.0 |
C8—C7—H7B | 108.9 | C208—C207—H20J | 109.0 |
H7A—C7—H7B | 107.8 | H20I—C207—H20J | 107.8 |
C7—C8—C14 | 111.8 (4) | C214—C208—C207 | 110.3 (4) |
C7—C8—C9 | 109.1 (5) | C214—C208—C209 | 109.7 (4) |
C14—C8—C9 | 110.4 (4) | C207—C208—C209 | 109.5 (4) |
C7—C8—H8A | 108.5 | C214—C208—H20K | 109.1 |
C14—C8—H8A | 108.5 | C207—C208—H20K | 109.1 |
C9—C8—H8A | 108.5 | C209—C208—H20K | 109.1 |
C11—C9—C8 | 112.5 (5) | C208—C209—C211 | 112.7 (4) |
C11—C9—C10 | 112.9 (6) | C208—C209—C210 | 113.3 (4) |
C8—C9—C10 | 112.3 (5) | C211—C209—C210 | 112.5 (4) |
C11—C9—H9A | 106.1 | C208—C209—H20L | 105.8 |
C8—C9—H9A | 106.1 | C211—C209—H20L | 105.8 |
C10—C9—H9A | 106.1 | C210—C209—H20L | 105.8 |
C5—C10—C9 | 110.3 (5) | C205—C210—C219 | 109.3 (5) |
C5—C10—C1 | 109.3 (6) | C205—C210—C201 | 107.4 (4) |
C9—C10—C1 | 107.4 (6) | C219—C210—C201 | 111.5 (5) |
C5—C10—C19 | 106.2 (6) | C205—C210—C209 | 109.7 (4) |
C9—C10—C19 | 113.9 (6) | C219—C210—C209 | 111.1 (4) |
C1—C10—C19 | 109.7 (8) | C201—C210—C209 | 107.7 (4) |
C9—C11—C12 | 111.7 (8) | C209—C211—C212 | 112.6 (4) |
C9—C11—H11A | 109.3 | C209—C211—H21A | 109.1 |
C12—C11—H11A | 109.3 | C212—C211—H21A | 109.1 |
C9—C11—H11B | 109.3 | C209—C211—H21B | 109.1 |
C12—C11—H11B | 109.3 | C212—C211—H21B | 109.1 |
H11A—C11—H11B | 107.9 | H21A—C211—H21B | 107.8 |
C13—C12—C11 | 109.2 (8) | C213—C212—C211 | 112.0 (4) |
C13—C12—H12A | 109.9 | C213—C212—H21C | 109.2 |
C11—C12—H12A | 109.8 | C211—C212—H21C | 109.2 |
C13—C12—H12B | 109.8 | C213—C212—H21D | 109.2 |
C11—C12—H12B | 109.8 | C211—C212—H21D | 109.2 |
H12A—C12—H12B | 108.3 | H21C—C212—H21D | 107.9 |
C14—C13—C12 | 106.9 (6) | C218—C213—C212 | 111.1 (5) |
C14—C13—C17 | 100.4 (5) | C218—C213—C214 | 112.9 (4) |
C12—C13—C17 | 114.3 (7) | C212—C213—C214 | 106.6 (4) |
C14—C13—C18 | 110.5 (6) | C218—C213—C217 | 109.8 (4) |
C12—C13—C18 | 114.0 (8) | C212—C213—C217 | 116.4 (4) |
C17—C13—C18 | 109.8 (6) | C214—C213—C217 | 99.6 (4) |
C13—C14—C15 | 104.1 (5) | C208—C214—C215 | 119.6 (4) |
C13—C14—C8 | 115.1 (5) | C208—C214—C213 | 115.2 (3) |
C15—C14—C8 | 120.2 (4) | C215—C214—C213 | 104.5 (4) |
C13—C14—H14A | 105.4 | C208—C214—H21E | 105.5 |
C15—C14—H14A | 105.4 | C215—C214—H21E | 105.5 |
C8—C14—H14A | 105.4 | C213—C214—H21E | 105.5 |
C14—C15—C16 | 104.7 (5) | C214—C215—C216 | 103.7 (4) |
C14—C15—H15A | 110.8 | C214—C215—H21F | 111.0 |
C16—C15—H15A | 110.8 | C216—C215—H21F | 111.0 |
C14—C15—H15B | 110.8 | C214—C215—H21G | 111.0 |
C16—C15—H15B | 110.8 | C216—C215—H21G | 111.0 |
H15A—C15—H15B | 108.9 | H21F—C215—H21G | 109.0 |
C15—C16—C17 | 105.9 (5) | C217—C216—C215 | 107.2 (4) |
C15—C16—H16A | 110.6 | C217—C216—H21H | 110.3 |
C17—C16—H16A | 110.6 | C215—C216—H21H | 110.3 |
C15—C16—H16B | 110.6 | C217—C216—H21I | 110.3 |
C17—C16—H16B | 110.6 | C215—C216—H21I | 110.3 |
H16A—C16—H16B | 108.7 | H21H—C216—H21I | 108.5 |
C28—C17—C16 | 116.6 (6) | C228—C217—C216 | 113.4 (5) |
C28—C17—C13 | 119.9 (8) | C228—C217—C213 | 116.2 (4) |
C16—C17—C13 | 103.4 (5) | C216—C217—C213 | 104.9 (4) |
C28—C17—H17A | 105.2 | C228—C217—H21J | 107.3 |
C16—C17—H17A | 105.2 | C216—C217—H21J | 107.3 |
C13—C17—H17A | 105.2 | C213—C217—H21J | 107.3 |
C13—C18—H18A | 109.5 | C213—C218—H21K | 109.5 |
C13—C18—H18B | 109.5 | C213—C218—H21L | 109.5 |
H18A—C18—H18B | 109.5 | H21K—C218—H21L | 109.5 |
C13—C18—H18C | 109.5 | C213—C218—H21M | 109.5 |
H18A—C18—H18C | 109.5 | H21K—C218—H21M | 109.5 |
H18B—C18—H18C | 109.5 | H21L—C218—H21M | 109.5 |
C10—C19—H19A | 109.5 | C210—C219—H21N | 109.5 |
C10—C19—H19B | 109.5 | C210—C219—H21O | 109.5 |
H19A—C19—H19B | 109.5 | H21N—C219—H21O | 109.5 |
C10—C19—H19C | 109.5 | C210—C219—H21P | 109.5 |
H19A—C19—H19C | 109.5 | H21N—C219—H21P | 109.5 |
H19B—C19—H19C | 109.5 | H21O—C219—H21P | 109.5 |
C21—O20—C3 | 117.4 (5) | C221—O220—C203 | 117.3 (4) |
O22—C21—O20 | 121.9 (6) | O222—C221—O220 | 124.9 (5) |
O22—C21—C23 | 125.3 (6) | O222—C221—C223 | 124.1 (5) |
O20—C21—C23 | 112.9 (5) | O220—C221—C223 | 111.0 (5) |
C21—C23—C24 | 112.6 (5) | C224—C223—C221 | 113.7 (5) |
C21—C23—H23A | 109.1 | C224—C223—H22A | 108.8 |
C24—C23—H23A | 109.1 | C221—C223—H22A | 108.8 |
C21—C23—H23B | 109.1 | C224—C223—H22B | 108.8 |
C24—C23—H23B | 109.1 | C221—C223—H22B | 108.8 |
H23A—C23—H23B | 107.8 | H22A—C223—H22B | 107.7 |
C25—C24—C23 | 116.4 (5) | C223—C224—C225 | 113.6 (5) |
C25—C24—H24A | 108.2 | C223—C224—H22C | 108.8 |
C23—C24—H24A | 108.2 | C225—C224—H22C | 108.8 |
C25—C24—H24B | 108.2 | C223—C224—H22D | 108.8 |
C23—C24—H24B | 108.2 | C225—C224—H22D | 108.8 |
H24A—C24—H24B | 107.3 | H22C—C224—H22D | 107.7 |
O26—C25—O27 | 121.5 (5) | O226—C225—O227 | 121.9 (5) |
O26—C25—C24 | 124.8 (6) | O226—C225—C224 | 123.2 (5) |
O27—C25—C24 | 113.6 (5) | O227—C225—C224 | 114.9 (5) |
C25—O27—H27 | 124.5 | C225—O227—H227 | 122.5 |
O29—C28—C30 | 116.6 (9) | O229—C228—C217 | 122.3 (7) |
O29—C28—C17 | 128.2 (9) | O229—C228—C230 | 122.5 (8) |
C30—C28—C17 | 110.3 (10) | C217—C228—C230 | 115.2 (8) |
C28—C30—H30A | 109.5 | C228—C230—H23C | 109.5 |
C28—C30—H30B | 109.5 | C228—C230—H23D | 109.5 |
H30A—C30—H30B | 109.5 | H23C—C230—H23D | 109.5 |
C28—C30—H30C | 109.5 | C228—C230—H23E | 109.5 |
H30A—C30—H30C | 109.5 | H23C—C230—H23E | 109.5 |
H30B—C30—H30C | 109.5 | H23D—C230—H23E | 109.5 |
C102—C101—C110 | 114.6 (5) | C310—C301—C302 | 114.8 (5) |
C102—C101—H10A | 108.6 | C310—C301—H30D | 108.6 |
C110—C101—H10A | 108.6 | C302—C301—H30D | 108.6 |
C102—C101—H10B | 108.6 | C310—C301—H30E | 108.6 |
C110—C101—H10B | 108.6 | C302—C301—H30E | 108.6 |
H10A—C101—H10B | 107.6 | H30D—C301—H30E | 107.5 |
C103—C102—C101 | 109.8 (4) | C303—C302—C301 | 111.2 (5) |
C103—C102—H10C | 109.7 | C303—C302—H30F | 109.4 |
C101—C102—H10C | 109.7 | C301—C302—H30F | 109.4 |
C103—C102—H10D | 109.7 | C303—C302—H30G | 109.4 |
C101—C102—H10D | 109.7 | C301—C302—H30G | 109.4 |
H10C—C102—H10D | 108.2 | H30F—C302—H30G | 108.0 |
O120—C103—C102 | 110.7 (4) | O320—C303—C302 | 111.2 (6) |
O120—C103—C104 | 106.7 (5) | O320—C303—C304 | 104.9 (5) |
C102—C103—C104 | 111.9 (5) | C302—C303—C304 | 110.5 (5) |
O120—C103—H10E | 109.1 | O320—C303—H30H | 110.0 |
C102—C103—H10E | 109.1 | C302—C303—H30H | 110.0 |
C104—C103—H10E | 109.1 | C304—C303—H30H | 110.0 |
C105—C104—C103 | 111.0 (5) | C305—C304—C303 | 110.3 (5) |
C105—C104—H10F | 109.4 | C305—C304—H30I | 109.6 |
C103—C104—H10F | 109.4 | C303—C304—H30I | 109.6 |
C105—C104—H10G | 109.4 | C305—C304—H30J | 109.6 |
C103—C104—H10G | 109.4 | C303—C304—H30J | 109.6 |
H10F—C104—H10G | 108.0 | H30I—C304—H30J | 108.1 |
C106—C105—C104 | 121.2 (5) | C306—C305—C304 | 119.5 (5) |
C106—C105—C110 | 121.7 (5) | C306—C305—C310 | 123.2 (5) |
C104—C105—C110 | 117.1 (4) | C304—C305—C310 | 117.2 (5) |
C105—C106—C107 | 127.6 (6) | C305—C306—C307 | 125.6 (5) |
C105—C106—H10H | 116.2 | C305—C306—H30K | 117.2 |
C107—C106—H10H | 116.2 | C307—C306—H30K | 117.2 |
C106—C107—C108 | 111.7 (5) | C306—C307—C308 | 113.7 (4) |
C106—C107—H10I | 109.3 | C306—C307—H30L | 108.8 |
C108—C107—H10I | 109.3 | C308—C307—H30L | 108.8 |
C106—C107—H10J | 109.3 | C306—C307—H30M | 108.8 |
C108—C107—H10J | 109.3 | C308—C307—H30M | 108.8 |
H10I—C107—H10J | 107.9 | H30L—C307—H30M | 107.7 |
C114—C108—C109 | 109.7 (4) | C314—C308—C307 | 111.1 (4) |
C114—C108—C107 | 110.2 (5) | C314—C308—C309 | 109.5 (4) |
C109—C108—C107 | 108.8 (5) | C307—C308—C309 | 109.8 (4) |
C114—C108—H10K | 109.4 | C314—C308—H30N | 108.8 |
C109—C108—H10K | 109.4 | C307—C308—H30N | 108.8 |
C107—C108—H10K | 109.4 | C309—C308—H30N | 108.8 |
C108—C109—C111 | 111.7 (4) | C311—C309—C310 | 113.7 (4) |
C108—C109—C110 | 113.0 (4) | C311—C309—C308 | 111.6 (4) |
C111—C109—C110 | 114.4 (4) | C310—C309—C308 | 113.1 (4) |
C108—C109—H10L | 105.6 | C311—C309—H30O | 105.9 |
C111—C109—H10L | 105.6 | C310—C309—H30O | 105.9 |
C110—C109—H10L | 105.6 | C308—C309—H30O | 105.9 |
C119—C110—C105 | 109.0 (5) | C305—C310—C301 | 109.5 (4) |
C119—C110—C101 | 108.6 (5) | C305—C310—C309 | 109.2 (4) |
C105—C110—C101 | 109.5 (4) | C301—C310—C309 | 109.0 (4) |
C119—C110—C109 | 111.1 (4) | C305—C310—C319 | 107.8 (4) |
C105—C110—C109 | 109.7 (4) | C301—C310—C319 | 108.8 (5) |
C101—C110—C109 | 108.9 (4) | C309—C310—C319 | 112.6 (4) |
C112—C111—C109 | 114.3 (4) | C312—C311—C309 | 114.1 (4) |
C112—C111—H11C | 108.7 | C312—C311—H31A | 108.7 |
C109—C111—H11C | 108.7 | C309—C311—H31A | 108.7 |
C112—C111—H11D | 108.7 | C312—C311—H31B | 108.7 |
C109—C111—H11D | 108.7 | C309—C311—H31B | 108.7 |
H11C—C111—H11D | 107.6 | H31A—C311—H31B | 107.6 |
C113—C112—C111 | 111.4 (4) | C313—C312—C311 | 111.6 (4) |
C113—C112—H11E | 109.3 | C313—C312—H31C | 109.3 |
C111—C112—H11E | 109.3 | C311—C312—H31C | 109.3 |
C113—C112—H11F | 109.3 | C313—C312—H31D | 109.3 |
C111—C112—H11F | 109.3 | C311—C312—H31D | 109.3 |
H11E—C112—H11F | 108.0 | H31C—C312—H31D | 108.0 |
C118—C113—C112 | 110.9 (5) | C312—C313—C314 | 108.2 (4) |
C118—C113—C114 | 114.0 (5) | C312—C313—C318 | 110.2 (4) |
C112—C113—C114 | 106.3 (4) | C314—C313—C318 | 112.9 (4) |
C118—C113—C117 | 110.3 (4) | C312—C313—C317 | 117.2 (4) |
C112—C113—C117 | 116.2 (4) | C314—C313—C317 | 99.0 (4) |
C114—C113—C117 | 98.7 (4) | C318—C313—C317 | 109.1 (4) |
C108—C114—C113 | 115.1 (4) | C308—C314—C313 | 115.6 (4) |
C108—C114—C115 | 117.8 (5) | C308—C314—C315 | 119.0 (4) |
C113—C114—C115 | 104.4 (5) | C313—C314—C315 | 104.5 (4) |
C108—C114—H11G | 106.2 | C308—C314—H31E | 105.5 |
C113—C114—H11G | 106.2 | C313—C314—H31E | 105.5 |
C115—C114—H11G | 106.2 | C315—C314—H31E | 105.5 |
C116—C115—C114 | 103.2 (5) | C316—C315—C314 | 103.3 (4) |
C116—C115—H11H | 111.1 | C316—C315—H31F | 111.1 |
C114—C115—H11H | 111.1 | C314—C315—H31F | 111.1 |
C116—C115—H11I | 111.1 | C316—C315—H31G | 111.1 |
C114—C115—H11I | 111.1 | C314—C315—H31G | 111.1 |
H11H—C115—H11I | 109.1 | H31F—C315—H31G | 109.1 |
C117—C116—C115 | 106.5 (5) | C317—C316—C315 | 107.9 (4) |
C117—C116—H11J | 110.4 | C317—C316—H31H | 110.1 |
C115—C116—H11J | 110.4 | C315—C316—H31H | 110.1 |
C117—C116—H11K | 110.4 | C317—C316—H31I | 110.1 |
C115—C116—H11K | 110.4 | C315—C316—H31I | 110.1 |
H11J—C116—H11K | 108.6 | H31H—C316—H31I | 108.4 |
C128—C117—C116 | 112.6 (5) | C328—C317—C316 | 114.3 (5) |
C128—C117—C113 | 115.7 (4) | C328—C317—C313 | 117.5 (4) |
C116—C117—C113 | 104.1 (5) | C316—C317—C313 | 103.0 (4) |
C128—C117—H11L | 108.0 | C328—C317—H31J | 107.2 |
C116—C117—H11L | 108.0 | C316—C317—H31J | 107.2 |
C113—C117—H11L | 108.0 | C313—C317—H31J | 107.2 |
C113—C118—H11M | 109.5 | C313—C318—H31K | 109.5 |
C113—C118—H11N | 109.5 | C313—C318—H31L | 109.5 |
H11M—C118—H11N | 109.5 | H31K—C318—H31L | 109.5 |
C113—C118—H11O | 109.5 | C313—C318—H31M | 109.5 |
H11M—C118—H11O | 109.5 | H31K—C318—H31M | 109.5 |
H11N—C118—H11O | 109.5 | H31L—C318—H31M | 109.5 |
C110—C119—H11P | 109.5 | C310—C319—H31N | 109.5 |
C110—C119—H11Q | 109.5 | C310—C319—H31O | 109.5 |
H11P—C119—H11Q | 109.5 | H31N—C319—H31O | 109.5 |
C110—C119—H11R | 109.5 | C310—C319—H31P | 109.5 |
H11P—C119—H11R | 109.5 | H31N—C319—H31P | 109.5 |
H11Q—C119—H11R | 109.5 | H31O—C319—H31P | 109.5 |
C121—O120—C103 | 118.8 (5) | C321—O320—C303 | 120.1 (5) |
O122—C121—O120 | 122.2 (6) | O322—C321—O320 | 120.9 (5) |
O122—C121—C123 | 121.8 (7) | O322—C321—C323 | 123.4 (6) |
O120—C121—C123 | 115.3 (6) | O320—C321—C323 | 115.3 (5) |
C124—C123—C121 | 113.8 (5) | C321—C323—C324 | 114.9 (5) |
C124—C123—H12C | 108.8 | C321—C323—H32A | 108.6 |
C121—C123—H12C | 108.8 | C324—C323—H32A | 108.6 |
C124—C123—H12D | 108.8 | C321—C323—H32B | 108.6 |
C121—C123—H12D | 108.8 | C324—C323—H32B | 108.6 |
H12C—C123—H12D | 107.7 | H32A—C323—H32B | 107.5 |
C123—C124—C125 | 115.8 (5) | C323—C324—C325 | 116.3 (5) |
C123—C124—H12E | 108.3 | C323—C324—H32C | 108.2 |
C125—C124—H12E | 108.3 | C325—C324—H32C | 108.2 |
C123—C124—H12F | 108.3 | C323—C324—H32D | 108.2 |
C125—C124—H12F | 108.3 | C325—C324—H32D | 108.2 |
H12E—C124—H12F | 107.4 | H32C—C324—H32D | 107.4 |
O126—C125—O127 | 122.5 (5) | O326—C325—O327 | 122.2 (5) |
O126—C125—C124 | 124.2 (5) | O326—C325—C324 | 124.4 (5) |
O127—C125—C124 | 113.4 (5) | O327—C325—C324 | 113.4 (5) |
C125—O127—H127 | 122.8 | C325—O327—H327 | 114.9 |
O129—C128—C130 | 120.7 (6) | O329—C328—C330 | 119.6 (6) |
O129—C128—C117 | 121.7 (6) | O329—C328—C317 | 120.7 (6) |
C130—C128—C117 | 117.6 (5) | C330—C328—C317 | 119.6 (5) |
C128—C130—H13A | 109.5 | C328—C330—H33A | 109.5 |
C128—C130—H13B | 109.5 | C328—C330—H33B | 109.5 |
H13A—C130—H13B | 109.5 | H33A—C330—H33B | 109.5 |
C128—C130—H13C | 109.5 | C328—C330—H33C | 109.5 |
H13A—C130—H13C | 109.5 | H33A—C330—H33C | 109.5 |
H13B—C130—H13C | 109.5 | H33B—C330—H33C | 109.5 |
| | | |
C10—C1—C2—C3 | −56.2 (13) | C210—C201—C202—C203 | −55.7 (8) |
C1—C2—C3—O20 | 178.6 (7) | C201—C202—C203—O220 | 179.6 (5) |
C1—C2—C3—C4 | 61.1 (10) | C201—C202—C203—C204 | 59.3 (7) |
O20—C3—C4—C5 | −175.1 (5) | O220—C203—C204—C205 | −178.1 (4) |
C2—C3—C4—C5 | −58.5 (8) | C202—C203—C204—C205 | −59.2 (6) |
C3—C4—C5—C6 | −127.1 (7) | C203—C204—C205—C206 | −121.3 (5) |
C3—C4—C5—C10 | 52.1 (8) | C203—C204—C205—C210 | 56.2 (6) |
C10—C5—C6—C7 | 1.0 (11) | C210—C205—C206—C207 | 2.6 (8) |
C4—C5—C6—C7 | −179.9 (6) | C204—C205—C206—C207 | 179.9 (5) |
C5—C6—C7—C8 | 12.6 (10) | C205—C206—C207—C208 | 14.7 (8) |
C6—C7—C8—C14 | −163.9 (5) | C206—C207—C208—C214 | −165.1 (4) |
C6—C7—C8—C9 | −41.6 (7) | C206—C207—C208—C209 | −44.2 (6) |
C7—C8—C9—C11 | −171.4 (8) | C214—C208—C209—C211 | −49.9 (5) |
C14—C8—C9—C11 | −48.2 (9) | C207—C208—C209—C211 | −171.2 (5) |
C7—C8—C9—C10 | 59.9 (7) | C214—C208—C209—C210 | −179.2 (4) |
C14—C8—C9—C10 | −176.9 (5) | C207—C208—C209—C210 | 59.6 (5) |
C6—C5—C10—C9 | 15.8 (9) | C206—C205—C210—C219 | −111.2 (6) |
C4—C5—C10—C9 | −163.4 (5) | C204—C205—C210—C219 | 71.4 (6) |
C6—C5—C10—C1 | 133.7 (8) | C206—C205—C210—C201 | 127.7 (5) |
C4—C5—C10—C1 | −45.5 (9) | C204—C205—C210—C201 | −49.7 (6) |
C6—C5—C10—C19 | −108.1 (7) | C206—C205—C210—C209 | 10.9 (7) |
C4—C5—C10—C19 | 72.8 (7) | C204—C205—C210—C209 | −166.6 (4) |
C11—C9—C10—C5 | −174.7 (7) | C202—C201—C210—C205 | 49.3 (7) |
C8—C9—C10—C5 | −46.2 (7) | C202—C201—C210—C219 | −70.5 (7) |
C11—C9—C10—C1 | 66.2 (9) | C202—C201—C210—C209 | 167.4 (5) |
C8—C9—C10—C1 | −165.2 (7) | C208—C209—C210—C205 | −41.9 (6) |
C11—C9—C10—C19 | −55.5 (9) | C211—C209—C210—C205 | −171.3 (5) |
C8—C9—C10—C19 | 73.1 (8) | C208—C209—C210—C219 | 79.0 (6) |
C2—C1—C10—C5 | 47.1 (12) | C211—C209—C210—C219 | −50.3 (6) |
C2—C1—C10—C9 | 166.7 (8) | C208—C209—C210—C201 | −158.6 (4) |
C2—C1—C10—C19 | −69.0 (11) | C211—C209—C210—C201 | 72.1 (6) |
C8—C9—C11—C12 | 51.8 (11) | C208—C209—C211—C212 | 49.5 (7) |
C10—C9—C11—C12 | −179.8 (8) | C210—C209—C211—C212 | 179.1 (5) |
C9—C11—C12—C13 | −58.6 (13) | C209—C211—C212—C213 | −53.7 (7) |
C11—C12—C13—C14 | 60.6 (11) | C211—C212—C213—C218 | −67.1 (6) |
C11—C12—C13—C17 | 170.7 (8) | C211—C212—C213—C214 | 56.3 (6) |
C11—C12—C13—C18 | −61.9 (10) | C211—C212—C213—C217 | 166.3 (5) |
C12—C13—C14—C15 | 165.2 (8) | C207—C208—C214—C215 | −55.8 (6) |
C17—C13—C14—C15 | 45.7 (7) | C209—C208—C214—C215 | −176.6 (4) |
C18—C13—C14—C15 | −70.2 (6) | C207—C208—C214—C213 | 178.4 (4) |
C12—C13—C14—C8 | −61.2 (9) | C209—C208—C214—C213 | 57.7 (5) |
C17—C13—C14—C8 | 179.3 (5) | C218—C213—C214—C208 | 61.8 (6) |
C18—C13—C14—C8 | 63.5 (7) | C212—C213—C214—C208 | −60.5 (5) |
C7—C8—C14—C13 | 176.1 (6) | C217—C213—C214—C208 | 178.2 (4) |
C9—C8—C14—C13 | 54.5 (7) | C218—C213—C214—C215 | −71.4 (5) |
C7—C8—C14—C15 | −58.2 (7) | C212—C213—C214—C215 | 166.3 (4) |
C9—C8—C14—C15 | −179.8 (5) | C217—C213—C214—C215 | 45.0 (5) |
C13—C14—C15—C16 | −31.7 (7) | C208—C214—C215—C216 | −165.4 (4) |
C8—C14—C15—C16 | −162.4 (5) | C213—C214—C215—C216 | −34.8 (6) |
C14—C15—C16—C17 | 4.9 (7) | C214—C215—C216—C217 | 10.1 (7) |
C15—C16—C17—C28 | 156.9 (10) | C215—C216—C217—C228 | 145.5 (6) |
C15—C16—C17—C13 | 23.0 (8) | C215—C216—C217—C213 | 17.7 (7) |
C14—C13—C17—C28 | −173.9 (9) | C218—C213—C217—C228 | −45.3 (7) |
C12—C13—C17—C28 | 72.1 (12) | C212—C213—C217—C228 | 82.0 (7) |
C18—C13—C17—C28 | −57.5 (10) | C214—C213—C217—C228 | −164.0 (6) |
C14—C13—C17—C16 | −41.9 (7) | C218—C213—C217—C216 | 80.8 (6) |
C12—C13—C17—C16 | −155.9 (8) | C212—C213—C217—C216 | −151.9 (5) |
C18—C13—C17—C16 | 74.5 (7) | C214—C213—C217—C216 | −37.9 (5) |
C2—C3—O20—C21 | 138.1 (7) | C202—C203—O220—C221 | 158.5 (5) |
C4—C3—O20—C21 | −102.8 (7) | C204—C203—O220—C221 | −80.7 (6) |
C3—O20—C21—O22 | −3.8 (12) | C203—O220—C221—O222 | 1.9 (8) |
C3—O20—C21—C23 | 177.6 (6) | C203—O220—C221—C223 | −179.0 (5) |
O22—C21—C23—C24 | −14.2 (12) | O222—C221—C223—C224 | −34.3 (9) |
O20—C21—C23—C24 | 164.4 (7) | O220—C221—C223—C224 | 146.6 (6) |
C21—C23—C24—C25 | −178.1 (6) | C221—C223—C224—C225 | −177.4 (6) |
C23—C24—C25—O26 | −5.2 (12) | C223—C224—C225—O226 | −28.4 (10) |
C23—C24—C25—O27 | 173.0 (8) | C223—C224—C225—O227 | 150.1 (7) |
C16—C17—C28—O29 | −12 (2) | C216—C217—C228—O229 | −11.4 (11) |
C13—C17—C28—O29 | 113.6 (16) | C213—C217—C228—O229 | 110.2 (8) |
C16—C17—C28—C30 | 141.5 (9) | C216—C217—C228—C230 | 167.7 (7) |
C13—C17—C28—C30 | −92.5 (13) | C213—C217—C228—C230 | −70.7 (9) |
C110—C101—C102—C103 | −57.0 (7) | C310—C301—C302—C303 | −54.7 (7) |
C101—C102—C103—O120 | 178.3 (5) | C301—C302—C303—O320 | 175.5 (5) |
C101—C102—C103—C104 | 59.4 (7) | C301—C302—C303—C304 | 59.4 (6) |
O120—C103—C104—C105 | −176.1 (5) | O320—C303—C304—C305 | −177.0 (5) |
C102—C103—C104—C105 | −54.8 (7) | C302—C303—C304—C305 | −57.0 (7) |
C103—C104—C105—C106 | −130.9 (7) | C303—C304—C305—C306 | −129.8 (6) |
C103—C104—C105—C110 | 48.0 (7) | C303—C304—C305—C310 | 51.0 (7) |
C104—C105—C106—C107 | −179.1 (8) | C304—C305—C306—C307 | −178.3 (5) |
C110—C105—C106—C107 | 2.0 (13) | C310—C305—C306—C307 | 0.9 (9) |
C105—C106—C107—C108 | 11.5 (14) | C305—C306—C307—C308 | 10.4 (8) |
C106—C107—C108—C114 | −161.3 (7) | C306—C307—C308—C314 | −159.8 (4) |
C106—C107—C108—C109 | −41.0 (9) | C306—C307—C308—C309 | −38.6 (6) |
C114—C108—C109—C111 | −47.6 (6) | C314—C308—C309—C311 | −49.4 (5) |
C107—C108—C109—C111 | −168.1 (5) | C307—C308—C309—C311 | −171.6 (4) |
C114—C108—C109—C110 | −178.3 (4) | C314—C308—C309—C310 | −179.1 (4) |
C107—C108—C109—C110 | 61.2 (6) | C307—C308—C309—C310 | 58.7 (5) |
C106—C105—C110—C119 | −106.4 (7) | C306—C305—C310—C301 | 136.5 (5) |
C104—C105—C110—C119 | 74.8 (6) | C304—C305—C310—C301 | −44.3 (6) |
C106—C105—C110—C101 | 135.0 (7) | C306—C305—C310—C309 | 17.3 (7) |
C104—C105—C110—C101 | −43.9 (7) | C304—C305—C310—C309 | −163.6 (4) |
C106—C105—C110—C109 | 15.5 (8) | C306—C305—C310—C319 | −105.3 (6) |
C104—C105—C110—C109 | −163.3 (5) | C304—C305—C310—C319 | 73.8 (6) |
C102—C101—C110—C119 | −71.0 (6) | C302—C301—C310—C305 | 44.9 (7) |
C102—C101—C110—C105 | 47.9 (6) | C302—C301—C310—C309 | 164.3 (5) |
C102—C101—C110—C109 | 167.9 (4) | C302—C301—C310—C319 | −72.6 (6) |
C108—C109—C110—C119 | 73.3 (6) | C311—C309—C310—C305 | −175.4 (4) |
C111—C109—C110—C119 | −56.0 (6) | C308—C309—C310—C305 | −46.8 (5) |
C108—C109—C110—C105 | −47.3 (6) | C311—C309—C310—C301 | 65.0 (5) |
C111—C109—C110—C105 | −176.6 (5) | C308—C309—C310—C301 | −166.4 (4) |
C108—C109—C110—C101 | −167.2 (5) | C311—C309—C310—C319 | −55.7 (6) |
C111—C109—C110—C101 | 63.5 (6) | C308—C309—C310—C319 | 72.8 (5) |
C108—C109—C111—C112 | 49.1 (6) | C310—C309—C311—C312 | −179.7 (4) |
C110—C109—C111—C112 | 179.1 (4) | C308—C309—C311—C312 | 50.9 (6) |
C109—C111—C112—C113 | −55.4 (6) | C309—C311—C312—C313 | −54.2 (6) |
C111—C112—C113—C118 | −66.5 (6) | C311—C312—C313—C314 | 54.7 (5) |
C111—C112—C113—C114 | 57.9 (6) | C311—C312—C313—C318 | −69.1 (5) |
C111—C112—C113—C117 | 166.5 (4) | C311—C312—C313—C317 | 165.4 (4) |
C109—C108—C114—C113 | 56.7 (6) | C307—C308—C314—C313 | 177.0 (4) |
C107—C108—C114—C113 | 176.4 (6) | C309—C308—C314—C313 | 55.6 (5) |
C109—C108—C114—C115 | −179.5 (6) | C307—C308—C314—C315 | −57.2 (6) |
C107—C108—C114—C115 | −59.7 (9) | C309—C308—C314—C315 | −178.6 (4) |
C118—C113—C114—C108 | 61.3 (6) | C312—C313—C314—C308 | −58.1 (5) |
C112—C113—C114—C108 | −61.2 (6) | C318—C313—C314—C308 | 64.1 (5) |
C117—C113—C114—C108 | 178.2 (5) | C317—C313—C314—C308 | 179.3 (4) |
C118—C113—C114—C115 | −69.4 (6) | C312—C313—C314—C315 | 169.1 (4) |
C112—C113—C114—C115 | 168.1 (5) | C318—C313—C314—C315 | −68.7 (5) |
C117—C113—C114—C115 | 47.5 (6) | C317—C313—C314—C315 | 46.5 (4) |
C108—C114—C115—C116 | −163.3 (6) | C308—C314—C315—C316 | −164.2 (4) |
C113—C114—C115—C116 | −34.3 (8) | C313—C314—C315—C316 | −33.3 (5) |
C114—C115—C116—C117 | 6.7 (9) | C314—C315—C316—C317 | 5.7 (6) |
C115—C116—C117—C128 | 148.7 (7) | C315—C316—C317—C328 | 151.2 (5) |
C115—C116—C117—C113 | 22.6 (8) | C315—C316—C317—C313 | 22.7 (6) |
C118—C113—C117—C128 | −46.9 (7) | C312—C313—C317—C328 | 75.7 (6) |
C112—C113—C117—C128 | 80.4 (6) | C314—C313—C317—C328 | −168.4 (5) |
C114—C113—C117—C128 | −166.6 (5) | C318—C313—C317—C328 | −50.3 (6) |
C118—C113—C117—C116 | 77.2 (6) | C312—C313—C317—C316 | −157.7 (5) |
C112—C113—C117—C116 | −155.5 (6) | C314—C313—C317—C316 | −41.9 (5) |
C114—C113—C117—C116 | −42.5 (6) | C318—C313—C317—C316 | 76.2 (5) |
C102—C103—O120—C121 | 82.8 (7) | C302—C303—O320—C321 | 95.0 (7) |
C104—C103—O120—C121 | −155.2 (6) | C304—C303—O320—C321 | −145.5 (6) |
C103—O120—C121—O122 | −10.5 (11) | C303—O320—C321—O322 | −5.0 (11) |
C103—O120—C121—C123 | 179.0 (5) | C303—O320—C321—C323 | −177.8 (6) |
O122—C121—C123—C124 | 30.4 (11) | O322—C321—C323—C324 | 36.2 (10) |
O120—C121—C123—C124 | −159.0 (7) | O320—C321—C323—C324 | −151.2 (7) |
C121—C123—C124—C125 | −178.3 (7) | C321—C323—C324—C325 | −175.3 (6) |
C123—C124—C125—O126 | 11.6 (11) | C323—C324—C325—O326 | 11.9 (10) |
C123—C124—C125—O127 | −170.1 (7) | C323—C324—C325—O327 | −168.3 (7) |
C116—C117—C128—O129 | −5.2 (10) | C316—C317—C328—O329 | 1.3 (8) |
C113—C117—C128—O129 | 114.3 (7) | C313—C317—C328—O329 | 122.1 (6) |
C116—C117—C128—C130 | 174.5 (6) | C316—C317—C328—C330 | 178.0 (6) |
C113—C117—C128—C130 | −65.9 (7) | C313—C317—C328—C330 | −61.2 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O27—H27···O226i | 0.89 | 1.77 | 2.635 (7) | 164 |
O127—H127···O326ii | 0.87 | 1.83 | 2.689 (6) | 167 |
O227—H227···O26iii | 0.94 | 1.77 | 2.683 (6) | 165 |
O327—H327···O126iv | 1.04 | 1.67 | 2.707 (5) | 174 |
Symmetry codes: (i) x, y−2, z; (ii) x, y+2, z+1; (iii) x, y+2, z; (iv) x, y−2, z−1. |
Experimental details
Crystal data |
Chemical formula | C25H36O5 |
Mr | 416.54 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 11.4692 (10), 11.8174 (12), 17.6837 (14) |
α, β, γ (°) | 96.925 (9), 104.907 (6), 95.201 (8) |
V (Å3) | 2280.7 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.5 × 0.3 × 0.3 |
|
Data collection |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9296, 7990, 5778 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.191, 1.26 |
No. of reflections | 7990 |
No. of parameters | 1082 |
No. of restraints | 795 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.96, −0.22 |
Selected geometric parameters (Å, º) topC3—O20 | 1.463 (7) | C203—O220 | 1.465 (6) |
C5—C6 | 1.299 (9) | C205—C206 | 1.327 (7) |
O20—C21 | 1.316 (8) | O220—C221 | 1.332 (7) |
C21—O22 | 1.150 (8) | C221—O222 | 1.190 (7) |
C21—C23 | 1.470 (8) | C221—C223 | 1.509 (7) |
C23—C24 | 1.498 (8) | C223—C224 | 1.454 (9) |
C24—C25 | 1.462 (8) | C224—C225 | 1.488 (8) |
C25—O26 | 1.197 (7) | C225—O226 | 1.193 (7) |
C25—O27 | 1.282 (7) | C225—O227 | 1.275 (7) |
O27—H27 | 0.8873 | O227—H227 | 0.9382 |
C28—O29 | 1.356 (14) | C228—O229 | 1.164 (10) |
C103—O120 | 1.464 (6) | C303—O320 | 1.470 (6) |
C105—C106 | 1.290 (8) | C305—C306 | 1.322 (8) |
O120—C121 | 1.281 (8) | O320—C321 | 1.281 (7) |
C121—O122 | 1.233 (9) | C321—O322 | 1.210 (7) |
C121—C123 | 1.478 (8) | C321—C323 | 1.464 (8) |
C123—C124 | 1.472 (9) | C323—C324 | 1.476 (8) |
C124—C125 | 1.492 (8) | C324—C325 | 1.486 (8) |
C125—O126 | 1.201 (7) | C325—O326 | 1.197 (7) |
C125—O127 | 1.299 (7) | C325—O327 | 1.307 (7) |
O127—H127 | 0.8727 | O327—H327 | 1.0366 |
C128—O129 | 1.203 (7) | C328—O329 | 1.208 (7) |
| | | |
C21—O20—C3 | 117.4 (5) | C221—O220—C203 | 117.3 (4) |
O20—C21—C23 | 112.9 (5) | O220—C221—C223 | 111.0 (5) |
O27—C25—C24 | 113.6 (5) | O227—C225—C224 | 114.9 (5) |
C25—O27—H27 | 124.5 | C225—O227—H227 | 122.5 |
C121—O120—C103 | 118.8 (5) | C321—O320—C303 | 120.1 (5) |
O120—C121—C123 | 115.3 (6) | O320—C321—C323 | 115.3 (5) |
O127—C125—C124 | 113.4 (5) | O327—C325—C324 | 113.4 (5) |
C125—O127—H127 | 122.8 | C325—O327—H327 | 114.9 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O27—H27···O226i | 0.89 | 1.77 | 2.635 (7) | 164 |
O127—H127···O326ii | 0.87 | 1.83 | 2.689 (6) | 167 |
O227—H227···O26iii | 0.94 | 1.77 | 2.683 (6) | 165 |
O327—H327···O126iv | 1.04 | 1.67 | 2.707 (5) | 174 |
Symmetry codes: (i) x, y−2, z; (ii) x, y+2, z+1; (iii) x, y+2, z; (iv) x, y−2, z−1. |
As part of our interest in the synthesis of hydrophilic steroid derivatives, we have studied the monoesterification of pregnenolone (Δ5-pregnen-3β-ol-20-one) with anhydride of dicarboxylic acids, aiming to obtain hemiesters able to form water soluble salts. Pregnenolone, progesterone and the vast majority of corticosteroids belong to the pregnanes, a family considered to be the largest individual group of steroids. Furthermore, pregnenolone is a key intermediate in the biosynthesis of cortisol and related steroids, included in the general metabolism of cholesterol (Voet & Voet, 1990). Some hemisuccinate derivatives of these compounds have been studied, although with poor structural characterization. For example, the powder X-ray diffraction pattern (Parson, 1966) and the hypnotic properties (Gyermek et al., 1968) of the hemisuccinate of progesterone have been described.
In the case of pregnenolone, the formation of esters using the alcoholysis of anhydrides has two possible outcomes, viz. the esterification of the OH group at C3 or of the ketone at C28, after reduction to the corresponding alcohol. In this work, we explore the first alternative. The title compound, (I), was prepared starting from pregnenolone, succinic anhydride and pyridine (see Experimental).
The asymmetric unit of (I) contains four independent molecules, with no evidence of pseudo- or non-crystallographic symmetry. Crystals belonging to this class, namely Z' = 4 in space group P1, are not uncommon, with 153 occurrences reported in the Cambridge Structural Database (CSD, Version 5.24; Allen & Kennard, 1993). Cholesterol hemimethanol solvate, for which the structure was recently redetermined (Shieh & Nordman, 2002), belongs to this class.
Each independent molecule (Figs. 1–4) adopts a similar geometry (Table 1), with the expected all-trans A/B/C/D junctions and C5═C6 bond lengths in the range 1.290 (8)–1.327 (7) Å (Table 1). The geometry of the A–D system is identical to that observed for two previously X-ray characterized pregnenolone derivatives (Kolb et al., 1987). The four molecules in the asymmetric unit are almost parallel to one another, approximately along the b axis of the unit cell. Intermolecular contacts are limited to classical double hydrogen bonds (Moulton & Zaworotko, 2001) involving free carboxylic acid groups (Table 2), forming two independent discrete dimers in the cell (Fig. 5). All four molecules have the same absolute configurations for the chiral centers, e.g. 3S, 8R, 9S, 10R, 13S, 14S and 17S for the C1-containing molecule. This unique hand precludes the possibility of a centrosymmetric structure, making the space group assignation unambiguous.
It is noteworthy that the X-ray structure of pregnenolone was previously reported in space group P21 with Z' = 1 (CSD refcode PREGOL). One reason that (I) crystallizes with Z' = 4 can be found in the succinic moiety. A least-squares fit (Sheldrick, 1998) of the four independent molecules, using all non-H atoms, clearly indicates that substantial deviations are observed for the carbonyl atoms O22, O122, O222 and O322. For instance, comparing the C1-molecule with the others, the r.m.s. deviations are 0.388, 0.317 and 0.324 Å for the C101-, C201- and C301-molecules, respectively, while the deviations from O22 are 1.245, 0.982 and 1.122 Å for O122, O222 and O322, respectively. These deviations are a consequence of the rotational freedom around the O20—C21 σ bond, whereas the A–D steroidal nucleus is unaffected by the flexibility of the lateral chain at C3 (Fig. 6). This is very probably valid for any steroid derivative, for which five- and six-membered rings are built-up essentially of Csp3 atoms, giving a rigid core.
Crystal structures with Z'>1 are generally unwelcome for X-ray single-crystal characterization, for the following two reasons: (i) for a given molecular complexity, the size of the unit cell, which is directly correlated to the size of the diffraction sphere, increases, lengthening data collection; and (ii) molecules in these crystals are generally not very densely packed, giving poorly diffracting samples (Lehmler et al., 2002). This phenomenon is also associated with low melting point compounds, sometimes close to room temperature (McCourt et al., 1996). However, these structures are of interest, because large Z' values do not appear accidentally. They may be related to packing conflicts (Kitaigorodskii, 1973), non-crystallographic symmetry induced by intermolecular contacts, cocrystallization phenomenon, etc. The limiting case, Z' → ∞, can be considered as a frontier between the crystalline and glassy states (Lehmler et al., 2002). Based on the same concept, soft matter, including nematic phases, would be characterized by Z → ∞.
In conclusion, we have found that for the pregnenolone derivative reported here, a Z' > 1 structure was obtained because of the contrast between a rigid core and a lateral chain with a high degree of rotational freedom. Obviously, this should be considered as an a posteriori explination as it is almost always not possible to predict the Z' value that will be observed in the crystalline state.