The absolute stereochemistry of the title compound, C
28H
33O
9·CHCl
3, has been determined by single-crystal X-ray diffraction by incorporation of the heavy-atom-containing solvent chloroform. The
A/
B,
B/
C and
C/
D ring junctions are all
trans-fused. Five-membered ring
E is equatorially attached to ring
D. The crystal structure is stabilized by weak intermolecular C—H
O interactions.
Supporting information
CCDC reference: 604550
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- Disorder in solvent or counterion
- R factor = 0.054
- wR factor = 0.165
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O9
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C29
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 43.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24C .. O5 .. 2.76 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B .. O8 .. 2.67 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.80 Deg.
CL3' -C29 -CL3 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.40 Deg.
CL1' -C29 -CL1 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.90 Deg.
CL2' -C29 -CL2 1.555 1.555 1.555
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.01
From the CIF: _reflns_number_total 5361
Count of symmetry unique reflns 3058
Completeness (_total/calc) 175.31%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2303
Fraction of Friedel pairs measured 0.753
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL ((Bruker, 2000); software used to prepare material for publication: SHELXTL.
(-)-Nomilin chloroform solvate
top
Crystal data top
C28H33O9·CHCl3 | F(000) = 1324 |
Mr = 632.91 | Dx = 1.385 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3156 reflections |
a = 8.599 (4) Å | θ = 2.5–19.9° |
b = 12.951 (6) Å | µ = 0.35 mm−1 |
c = 27.252 (12) Å | T = 298 K |
V = 3035 (2) Å3 | Prism, colourless |
Z = 4 | 0.45 × 0.38 × 0.31 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5361 independent reflections |
Radiation source: fine-focus sealed tube | 3162 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→10 |
Tmin = 0.857, Tmax = 0.898 | k = −15→14 |
16041 measured reflections | l = −27→32 |
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)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.165 | w = 1/[σ2(Fo2) + (0.0796P)2 + 0.9994P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.016 |
5361 reflections | Δρmax = 0.32 e Å−3 |
404 parameters | Δρmin = −0.29 e Å−3 |
138 restraints | Absolute structure: Flack (1983), 2303 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.10 (14) |
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 | Occ. (<1) |
Cl1 | 0.9764 (13) | 0.5117 (5) | 0.3464 (5) | 0.139 (3) | 0.615 (19) |
Cl2 | 0.8483 (10) | 0.3190 (5) | 0.3254 (4) | 0.173 (3) | 0.615 (19) |
Cl3 | 1.0178 (11) | 0.3485 (11) | 0.4127 (3) | 0.179 (4) | 0.615 (19) |
Cl1' | 1.004 (2) | 0.5093 (9) | 0.3643 (8) | 0.150 (5) | 0.385 (19) |
Cl2' | 0.910 (2) | 0.3440 (14) | 0.3051 (6) | 0.207 (5) | 0.385 (19) |
Cl3' | 0.998 (2) | 0.3059 (11) | 0.4008 (5) | 0.174 (5) | 0.385 (19) |
O1 | −0.0023 (4) | 0.2984 (2) | 0.72700 (10) | 0.0534 (8) | |
O2 | −0.1624 (5) | 0.1963 (3) | 0.69016 (13) | 0.0731 (11) | |
O3 | 0.0345 (3) | 0.3556 (2) | 0.60736 (10) | 0.0485 (8) | |
O4 | −0.1338 (6) | 0.3518 (4) | 0.54467 (16) | 0.1087 (16) | |
O5 | 0.5194 (4) | 0.5546 (3) | 0.67950 (12) | 0.0659 (9) | |
O6 | 0.3947 (4) | 0.7595 (2) | 0.58078 (11) | 0.0513 (8) | |
O7 | 0.6450 (4) | 0.6671 (3) | 0.52380 (12) | 0.0612 (9) | |
O8 | 0.7971 (4) | 0.7337 (3) | 0.58006 (13) | 0.0726 (10) | |
O9 | 0.6380 (7) | 0.4822 (4) | 0.40481 (18) | 0.1157 (18) | |
C1 | −0.1146 (6) | 0.2837 (4) | 0.69400 (16) | 0.0517 (12) | |
C2 | −0.1776 (6) | 0.3694 (3) | 0.66366 (17) | 0.0530 (12) | |
H2A | −0.2832 | 0.3850 | 0.6632 | 0.064* | |
C3 | −0.0612 (5) | 0.4304 (3) | 0.63345 (14) | 0.0407 (10) | |
H3A | −0.1201 | 0.4691 | 0.6088 | 0.049* | |
C4 | 0.0463 (5) | 0.5074 (3) | 0.65964 (14) | 0.0380 (9) | |
C5 | 0.1660 (5) | 0.5466 (3) | 0.62080 (13) | 0.0363 (9) | |
H5A | 0.2250 | 0.4846 | 0.6119 | 0.044* | |
C6 | 0.2930 (5) | 0.6240 (3) | 0.63898 (14) | 0.0377 (10) | |
C7 | 0.3791 (5) | 0.5664 (3) | 0.67925 (15) | 0.0441 (10) | |
C8 | 0.2780 (5) | 0.5226 (3) | 0.71881 (15) | 0.0475 (11) | |
H8A | 0.2319 | 0.5791 | 0.7371 | 0.057* | |
H8B | 0.3424 | 0.4834 | 0.7413 | 0.057* | |
C9 | 0.1460 (5) | 0.4516 (3) | 0.69945 (14) | 0.0421 (10) | |
H9A | 0.1992 | 0.3957 | 0.6820 | 0.051* | |
C10 | 0.0637 (6) | 0.3985 (3) | 0.74359 (15) | 0.0507 (12) | |
C11 | 0.1067 (5) | 0.5876 (3) | 0.57168 (15) | 0.0459 (11) | |
H11A | 0.0096 | 0.5539 | 0.5632 | 0.055* | |
H11B | 0.0877 | 0.6613 | 0.5741 | 0.055* | |
C12 | 0.2281 (5) | 0.5665 (4) | 0.53206 (15) | 0.0494 (11) | |
H12A | 0.2093 | 0.6125 | 0.5046 | 0.059* | |
H12B | 0.2151 | 0.4963 | 0.5204 | 0.059* | |
C13 | 0.3985 (5) | 0.5807 (3) | 0.54956 (14) | 0.0418 (10) | |
C14 | 0.3973 (5) | 0.6516 (3) | 0.59457 (14) | 0.0391 (10) | |
C15 | 0.5340 (5) | 0.7188 (3) | 0.60161 (17) | 0.0483 (11) | |
H15A | 0.5574 | 0.7393 | 0.6354 | 0.058* | |
C16 | 0.6683 (6) | 0.7070 (4) | 0.56815 (19) | 0.0533 (12) | |
C17 | 0.4901 (6) | 0.6359 (3) | 0.50815 (15) | 0.0503 (11) | |
H17A | 0.4322 | 0.6978 | 0.4983 | 0.060* | |
C18 | 0.5167 (7) | 0.5701 (4) | 0.46333 (17) | 0.0595 (13) | |
C19 | 0.6545 (9) | 0.5410 (5) | 0.4459 (2) | 0.099 (2) | |
H19A | 0.7495 | 0.5584 | 0.4599 | 0.119* | |
C20 | 0.4843 (11) | 0.4750 (5) | 0.3971 (2) | 0.091 (2) | |
H20A | 0.4390 | 0.4384 | 0.3715 | 0.109* | |
C21 | 0.4057 (9) | 0.5269 (5) | 0.43090 (19) | 0.0859 (19) | |
H21A | 0.2982 | 0.5336 | 0.4329 | 0.103* | |
C22 | −0.0149 (8) | 0.3236 (4) | 0.56235 (19) | 0.0652 (14) | |
C23 | 0.1015 (8) | 0.2550 (5) | 0.53875 (19) | 0.0839 (18) | |
H23A | 0.0515 | 0.2141 | 0.5139 | 0.126* | |
H23B | 0.1464 | 0.2103 | 0.5630 | 0.126* | |
H23C | 0.1818 | 0.2961 | 0.5240 | 0.126* | |
C24 | −0.0598 (5) | 0.5954 (3) | 0.67788 (16) | 0.0507 (12) | |
H24A | −0.0701 | 0.6465 | 0.6526 | 0.076* | |
H24B | −0.0148 | 0.6264 | 0.7066 | 0.076* | |
H24C | −0.1604 | 0.5681 | 0.6858 | 0.076* | |
C25 | 0.2318 (6) | 0.7255 (3) | 0.66129 (17) | 0.0563 (12) | |
H25A | 0.3174 | 0.7714 | 0.6674 | 0.084* | |
H25B | 0.1793 | 0.7110 | 0.6916 | 0.084* | |
H25C | 0.1605 | 0.7574 | 0.6388 | 0.084* | |
C26 | 0.1807 (7) | 0.3583 (4) | 0.78089 (18) | 0.0724 (16) | |
H26A | 0.1309 | 0.3089 | 0.8020 | 0.109* | |
H26B | 0.2193 | 0.4147 | 0.8002 | 0.109* | |
H26C | 0.2656 | 0.3257 | 0.7640 | 0.109* | |
C27 | −0.0613 (7) | 0.4595 (4) | 0.77091 (17) | 0.0684 (16) | |
H27A | −0.0906 | 0.4229 | 0.8001 | 0.103* | |
H27C | −0.1506 | 0.4678 | 0.7502 | 0.103* | |
H27D | −0.0212 | 0.5262 | 0.7796 | 0.103* | |
C28 | 0.4823 (6) | 0.4791 (3) | 0.56219 (16) | 0.0527 (12) | |
H28C | 0.4434 | 0.4528 | 0.5928 | 0.079* | |
H28D | 0.5920 | 0.4916 | 0.5650 | 0.079* | |
H28A | 0.4639 | 0.4294 | 0.5367 | 0.079* | |
C29 | 1.0102 (9) | 0.3821 (5) | 0.3526 (2) | 0.108 (2) | |
H29 | 1.1066 | 0.3626 | 0.3359 | 0.130* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.115 (5) | 0.091 (3) | 0.210 (7) | 0.011 (3) | 0.071 (5) | 0.031 (3) |
Cl2 | 0.183 (5) | 0.153 (4) | 0.183 (5) | −0.060 (4) | 0.039 (5) | −0.077 (4) |
Cl3 | 0.154 (5) | 0.212 (8) | 0.170 (5) | −0.024 (5) | −0.046 (5) | 0.063 (5) |
Cl1' | 0.122 (7) | 0.094 (6) | 0.234 (12) | −0.024 (5) | 0.014 (8) | 0.004 (6) |
Cl2' | 0.180 (10) | 0.276 (11) | 0.165 (8) | −0.054 (8) | 0.004 (7) | −0.025 (8) |
Cl3' | 0.211 (10) | 0.134 (7) | 0.178 (8) | 0.069 (6) | 0.085 (8) | 0.091 (6) |
O1 | 0.065 (2) | 0.0471 (16) | 0.0477 (17) | −0.0145 (16) | −0.0056 (17) | 0.0020 (14) |
O2 | 0.090 (3) | 0.057 (2) | 0.072 (2) | −0.027 (2) | −0.014 (2) | 0.0021 (18) |
O3 | 0.0531 (19) | 0.0502 (16) | 0.0422 (16) | −0.0045 (15) | −0.0044 (15) | −0.0094 (14) |
O4 | 0.099 (4) | 0.150 (4) | 0.077 (3) | 0.014 (3) | −0.042 (3) | −0.033 (3) |
O5 | 0.044 (2) | 0.087 (2) | 0.067 (2) | −0.0041 (19) | −0.0001 (17) | 0.0213 (18) |
O6 | 0.0534 (19) | 0.0370 (16) | 0.0635 (19) | 0.0032 (14) | 0.0097 (16) | 0.0089 (14) |
O7 | 0.057 (2) | 0.069 (2) | 0.057 (2) | −0.0035 (17) | 0.0175 (18) | 0.0064 (17) |
O8 | 0.049 (2) | 0.086 (3) | 0.083 (3) | −0.0103 (19) | 0.0070 (19) | 0.021 (2) |
O9 | 0.135 (5) | 0.112 (4) | 0.100 (3) | −0.026 (3) | 0.069 (3) | −0.038 (3) |
C1 | 0.059 (3) | 0.050 (3) | 0.046 (3) | −0.013 (2) | 0.004 (2) | −0.002 (2) |
C2 | 0.039 (3) | 0.058 (3) | 0.062 (3) | −0.006 (2) | 0.004 (2) | 0.009 (2) |
C3 | 0.038 (2) | 0.043 (2) | 0.042 (2) | −0.001 (2) | −0.0020 (19) | −0.0016 (19) |
C4 | 0.038 (2) | 0.037 (2) | 0.038 (2) | −0.0010 (18) | 0.0018 (19) | 0.0024 (18) |
C5 | 0.034 (2) | 0.037 (2) | 0.038 (2) | −0.0005 (18) | 0.0003 (18) | −0.0016 (17) |
C6 | 0.037 (2) | 0.037 (2) | 0.039 (2) | −0.0015 (19) | 0.0069 (19) | −0.0032 (18) |
C7 | 0.044 (3) | 0.047 (2) | 0.041 (2) | −0.005 (2) | −0.001 (2) | −0.001 (2) |
C8 | 0.046 (3) | 0.057 (3) | 0.039 (2) | −0.014 (2) | 0.002 (2) | −0.001 (2) |
C9 | 0.045 (3) | 0.045 (2) | 0.036 (2) | −0.006 (2) | −0.002 (2) | −0.0056 (19) |
C10 | 0.066 (3) | 0.048 (2) | 0.039 (2) | −0.019 (2) | 0.002 (2) | −0.004 (2) |
C11 | 0.045 (3) | 0.044 (2) | 0.048 (2) | 0.005 (2) | 0.003 (2) | 0.005 (2) |
C12 | 0.057 (3) | 0.051 (3) | 0.040 (2) | 0.003 (2) | 0.005 (2) | 0.005 (2) |
C13 | 0.049 (3) | 0.042 (2) | 0.035 (2) | 0.002 (2) | 0.008 (2) | 0.0049 (18) |
C14 | 0.042 (2) | 0.030 (2) | 0.045 (2) | 0.0038 (18) | 0.004 (2) | 0.0058 (18) |
C15 | 0.045 (3) | 0.048 (2) | 0.052 (3) | −0.003 (2) | 0.002 (2) | 0.004 (2) |
C16 | 0.041 (3) | 0.054 (3) | 0.065 (3) | −0.001 (2) | 0.009 (3) | 0.020 (3) |
C17 | 0.057 (3) | 0.053 (3) | 0.041 (2) | 0.002 (2) | 0.009 (2) | 0.009 (2) |
C18 | 0.073 (4) | 0.059 (3) | 0.047 (3) | −0.002 (3) | 0.022 (3) | 0.008 (2) |
C19 | 0.099 (5) | 0.105 (5) | 0.092 (5) | −0.021 (4) | 0.049 (4) | −0.035 (4) |
C20 | 0.131 (6) | 0.096 (4) | 0.044 (3) | −0.003 (5) | 0.022 (4) | −0.009 (3) |
C21 | 0.105 (5) | 0.107 (5) | 0.046 (3) | 0.020 (4) | 0.004 (3) | −0.003 (3) |
C22 | 0.079 (4) | 0.068 (3) | 0.048 (3) | −0.009 (3) | −0.010 (3) | −0.012 (2) |
C23 | 0.116 (5) | 0.079 (4) | 0.057 (3) | 0.008 (4) | 0.007 (3) | −0.022 (3) |
C24 | 0.048 (3) | 0.050 (3) | 0.054 (3) | 0.004 (2) | 0.016 (2) | −0.003 (2) |
C25 | 0.062 (3) | 0.042 (2) | 0.065 (3) | −0.003 (2) | 0.019 (3) | −0.011 (2) |
C26 | 0.086 (4) | 0.080 (4) | 0.051 (3) | −0.038 (3) | −0.011 (3) | 0.016 (3) |
C27 | 0.090 (4) | 0.068 (3) | 0.047 (3) | −0.027 (3) | 0.025 (3) | −0.011 (2) |
C28 | 0.066 (3) | 0.044 (2) | 0.048 (2) | 0.010 (2) | 0.015 (2) | 0.003 (2) |
C29 | 0.103 (5) | 0.101 (5) | 0.120 (5) | 0.017 (4) | 0.029 (5) | −0.001 (4) |
Geometric parameters (Å, º) top
Cl1—C29 | 1.712 (10) | C10—C26 | 1.522 (7) |
Cl2—C29 | 1.776 (10) | C11—C12 | 1.527 (6) |
Cl3—C29 | 1.696 (10) | C11—H11A | 0.9700 |
Cl1'—C29 | 1.679 (13) | C11—H11B | 0.9700 |
Cl2'—C29 | 1.633 (11) | C12—C13 | 1.552 (6) |
Cl3'—C29 | 1.646 (11) | C12—H12A | 0.9700 |
O1—C1 | 1.333 (6) | C12—H12B | 0.9700 |
O1—C10 | 1.487 (5) | C13—C14 | 1.532 (6) |
O2—C1 | 1.208 (5) | C13—C28 | 1.540 (6) |
O3—C22 | 1.363 (6) | C13—C17 | 1.551 (6) |
O3—C3 | 1.456 (5) | C14—C15 | 1.475 (6) |
O4—C22 | 1.187 (7) | C15—C16 | 1.479 (6) |
O5—C7 | 1.216 (5) | C15—H15A | 0.9800 |
O6—C15 | 1.426 (5) | C17—C18 | 1.508 (6) |
O6—C14 | 1.447 (5) | C17—H17A | 0.9800 |
O7—C16 | 1.329 (6) | C18—C19 | 1.331 (8) |
O7—C17 | 1.456 (6) | C18—C21 | 1.417 (8) |
O8—C16 | 1.205 (6) | C19—H19A | 0.9300 |
O9—C20 | 1.341 (9) | C20—C21 | 1.326 (8) |
O9—C19 | 1.361 (7) | C20—H20A | 0.9300 |
C1—C2 | 1.487 (7) | C21—H21A | 0.9300 |
C2—C3 | 1.517 (6) | C22—C23 | 1.486 (8) |
C2—H2A | 0.9300 | C23—H23A | 0.9600 |
C3—C4 | 1.536 (6) | C23—H23B | 0.9600 |
C3—H3A | 0.9800 | C23—H23C | 0.9600 |
C4—C24 | 1.542 (6) | C24—H24A | 0.9600 |
C4—C5 | 1.561 (5) | C24—H24B | 0.9600 |
C4—C9 | 1.560 (6) | C24—H24C | 0.9600 |
C5—C11 | 1.528 (5) | C25—H25A | 0.9600 |
C5—C6 | 1.564 (5) | C25—H25B | 0.9600 |
C5—H5A | 0.9800 | C25—H25C | 0.9600 |
C6—C7 | 1.520 (6) | C26—H26A | 0.9600 |
C6—C25 | 1.541 (6) | C26—H26B | 0.9600 |
C6—C14 | 1.548 (6) | C26—H26C | 0.9600 |
C7—C8 | 1.496 (6) | C27—H27A | 0.9600 |
C8—C9 | 1.553 (6) | C27—H27C | 0.9600 |
C8—H8A | 0.9700 | C27—H27D | 0.9600 |
C8—H8B | 0.9700 | C28—H28C | 0.9600 |
C9—C10 | 1.556 (6) | C28—H28D | 0.9600 |
C9—H9A | 0.9800 | C28—H28A | 0.9600 |
C10—C27 | 1.527 (7) | C29—H29 | 0.9800 |
| | | |
C1—O1—C10 | 127.3 (3) | C14—C15—H15A | 116.5 |
C22—O3—C3 | 117.7 (4) | C16—C15—H15A | 116.5 |
C15—O6—C14 | 61.8 (3) | O8—C16—O7 | 119.7 (4) |
C16—O7—C17 | 120.8 (3) | O8—C16—C15 | 121.5 (5) |
C20—O9—C19 | 105.7 (5) | O7—C16—C15 | 118.9 (4) |
O2—C1—O1 | 116.0 (4) | O7—C17—C18 | 104.8 (4) |
O2—C1—C2 | 121.8 (5) | O7—C17—C13 | 112.3 (4) |
O1—C1—C2 | 122.2 (4) | C18—C17—C13 | 113.9 (4) |
C1—C2—C3 | 116.7 (4) | O7—C17—H17A | 108.5 |
C1—C2—H2A | 121.6 | C18—C17—H17A | 108.5 |
C3—C2—H2A | 121.6 | C13—C17—H17A | 108.5 |
O3—C3—C2 | 106.9 (3) | C19—C18—C21 | 105.4 (5) |
O3—C3—C4 | 108.6 (3) | C19—C18—C17 | 125.8 (6) |
C2—C3—C4 | 118.9 (3) | C21—C18—C17 | 128.8 (5) |
O3—C3—H3A | 107.3 | C18—C19—O9 | 111.0 (6) |
C2—C3—H3A | 107.3 | C18—C19—H19A | 124.5 |
C4—C3—H3A | 107.3 | O9—C19—H19A | 124.5 |
C3—C4—C24 | 105.9 (3) | C21—C20—O9 | 111.0 (6) |
C3—C4—C5 | 107.0 (3) | C21—C20—H20A | 124.5 |
C24—C4—C5 | 111.6 (3) | O9—C20—H20A | 124.5 |
C3—C4—C9 | 110.7 (3) | C20—C21—C18 | 106.8 (7) |
C24—C4—C9 | 116.3 (3) | C20—C21—H21A | 126.6 |
C5—C4—C9 | 105.0 (3) | C18—C21—H21A | 126.6 |
C11—C5—C4 | 119.2 (3) | O4—C22—O3 | 122.7 (5) |
C11—C5—C6 | 106.7 (3) | O4—C22—C23 | 126.0 (5) |
C4—C5—C6 | 117.0 (3) | O3—C22—C23 | 111.2 (5) |
C11—C5—H5A | 104.0 | C22—C23—H23A | 109.5 |
C4—C5—H5A | 104.0 | C22—C23—H23B | 109.5 |
C6—C5—H5A | 104.0 | H23A—C23—H23B | 109.5 |
C7—C6—C25 | 107.5 (3) | C22—C23—H23C | 109.5 |
C7—C6—C14 | 113.3 (3) | H23A—C23—H23C | 109.5 |
C25—C6—C14 | 108.0 (3) | H23B—C23—H23C | 109.5 |
C7—C6—C5 | 104.7 (3) | C4—C24—H24A | 109.5 |
C25—C6—C5 | 115.7 (3) | C4—C24—H24B | 109.5 |
C14—C6—C5 | 107.8 (3) | H24A—C24—H24B | 109.5 |
O5—C7—C8 | 121.7 (4) | C4—C24—H24C | 109.5 |
O5—C7—C6 | 123.3 (4) | H24A—C24—H24C | 109.5 |
C8—C7—C6 | 115.0 (4) | H24B—C24—H24C | 109.5 |
C7—C8—C9 | 113.8 (3) | C6—C25—H25A | 109.5 |
C7—C8—H8A | 108.8 | C6—C25—H25B | 109.5 |
C9—C8—H8A | 108.8 | H25A—C25—H25B | 109.5 |
C7—C8—H8B | 108.8 | C6—C25—H25C | 109.5 |
C9—C8—H8B | 108.8 | H25A—C25—H25C | 109.5 |
H8A—C8—H8B | 107.7 | H25B—C25—H25C | 109.5 |
C10—C9—C8 | 109.3 (3) | C10—C26—H26A | 109.5 |
C10—C9—C4 | 119.5 (4) | C10—C26—H26B | 109.5 |
C8—C9—C4 | 111.3 (3) | H26A—C26—H26B | 109.5 |
C10—C9—H9A | 105.1 | C10—C26—H26C | 109.5 |
C8—C9—H9A | 105.1 | H26A—C26—H26C | 109.5 |
C4—C9—H9A | 105.1 | H26B—C26—H26C | 109.5 |
O1—C10—C27 | 109.3 (4) | C10—C27—H27A | 109.5 |
O1—C10—C26 | 99.0 (3) | C10—C27—H27C | 109.5 |
C27—C10—C26 | 108.5 (4) | H27A—C27—H27C | 109.5 |
O1—C10—C9 | 108.9 (3) | C10—C27—H27D | 109.5 |
C27—C10—C9 | 117.9 (4) | H27A—C27—H27D | 109.5 |
C26—C10—C9 | 111.5 (4) | H27C—C27—H27D | 109.5 |
C12—C11—C5 | 109.2 (3) | C13—C28—H28C | 109.5 |
C12—C11—H11A | 109.8 | C13—C28—H28D | 109.5 |
C5—C11—H11A | 109.8 | H28C—C28—H28D | 109.5 |
C12—C11—H11B | 109.8 | C13—C28—H28A | 109.5 |
C5—C11—H11B | 109.8 | H28C—C28—H28A | 109.5 |
H11A—C11—H11B | 108.3 | H28D—C28—H28A | 109.5 |
C11—C12—C13 | 114.0 (3) | Cl2'—C29—Cl3' | 114.8 (8) |
C11—C12—H12A | 108.7 | Cl2'—C29—Cl1' | 115.5 (9) |
C13—C12—H12A | 108.7 | Cl3'—C29—Cl1' | 115.8 (8) |
C11—C12—H12B | 108.7 | Cl2'—C29—Cl3 | 135.1 (8) |
C13—C12—H12B | 108.7 | Cl3'—C29—Cl3 | 22.8 (6) |
H12A—C12—H12B | 107.6 | Cl1'—C29—Cl3 | 94.0 (8) |
C14—C13—C28 | 109.7 (3) | Cl2'—C29—Cl1 | 97.4 (8) |
C14—C13—C12 | 108.1 (3) | Cl3'—C29—Cl1 | 131.1 (7) |
C28—C13—C12 | 114.1 (4) | Cl1'—C29—Cl1 | 18.4 (9) |
C14—C13—C17 | 108.0 (3) | Cl3—C29—Cl1 | 110.7 (6) |
C28—C13—C17 | 108.6 (4) | Cl2'—C29—Cl2 | 27.9 (6) |
C12—C13—C17 | 108.1 (3) | Cl3'—C29—Cl2 | 90.5 (8) |
O6—C14—C15 | 58.4 (3) | Cl1'—C29—Cl2 | 120.4 (9) |
O6—C14—C13 | 111.7 (3) | Cl3—C29—Cl2 | 108.3 (5) |
C15—C14—C13 | 116.9 (4) | Cl1—C29—Cl2 | 106.1 (6) |
O6—C14—C6 | 114.7 (3) | Cl2'—C29—H29 | 90.0 |
C15—C14—C6 | 119.8 (3) | Cl3'—C29—H29 | 105.6 |
C13—C14—C6 | 119.4 (3) | Cl1'—C29—H29 | 111.7 |
O6—C15—C14 | 59.8 (3) | Cl3—C29—H29 | 110.5 |
O6—C15—C16 | 116.6 (4) | Cl1—C29—H29 | 110.5 |
C14—C15—C16 | 118.8 (4) | Cl2—C29—H29 | 110.5 |
O6—C15—H15A | 116.5 | | |
| | | |
C10—O1—C1—O2 | −171.9 (4) | C11—C12—C13—C28 | 100.3 (4) |
C10—O1—C1—C2 | 8.1 (7) | C11—C12—C13—C17 | −138.7 (4) |
O2—C1—C2—C3 | −124.3 (5) | C15—O6—C14—C13 | −109.1 (4) |
O1—C1—C2—C3 | 55.8 (6) | C15—O6—C14—C6 | 111.0 (4) |
C22—O3—C3—C2 | 89.3 (4) | C28—C13—C14—O6 | 151.1 (4) |
C22—O3—C3—C4 | −141.3 (4) | C12—C13—C14—O6 | −83.8 (4) |
C1—C2—C3—O3 | 48.8 (5) | C17—C13—C14—O6 | 32.9 (5) |
C1—C2—C3—C4 | −74.5 (5) | C28—C13—C14—C15 | 86.6 (4) |
O3—C3—C4—C24 | 169.3 (3) | C12—C13—C14—C15 | −148.4 (4) |
C2—C3—C4—C24 | −68.2 (4) | C17—C13—C14—C15 | −31.6 (5) |
O3—C3—C4—C5 | 50.1 (4) | C28—C13—C14—C6 | −71.1 (5) |
C2—C3—C4—C5 | 172.6 (4) | C12—C13—C14—C6 | 54.0 (5) |
O3—C3—C4—C9 | −63.8 (4) | C17—C13—C14—C6 | 170.7 (4) |
C2—C3—C4—C9 | 58.7 (5) | C7—C6—C14—O6 | −127.2 (4) |
C3—C4—C5—C11 | 51.1 (4) | C25—C6—C14—O6 | −8.2 (5) |
C24—C4—C5—C11 | −64.3 (4) | C5—C6—C14—O6 | 117.4 (4) |
C9—C4—C5—C11 | 168.8 (3) | C7—C6—C14—C15 | −60.8 (5) |
C3—C4—C5—C6 | −178.1 (3) | C25—C6—C14—C15 | 58.1 (5) |
C24—C4—C5—C6 | 66.5 (4) | C5—C6—C14—C15 | −176.2 (3) |
C9—C4—C5—C6 | −60.4 (4) | C7—C6—C14—C13 | 96.2 (4) |
C11—C5—C6—C7 | −164.6 (3) | C25—C6—C14—C13 | −144.8 (4) |
C4—C5—C6—C7 | 59.0 (4) | C5—C6—C14—C13 | −19.2 (5) |
C11—C5—C6—C25 | 77.3 (4) | C14—O6—C15—C16 | 109.3 (4) |
C4—C5—C6—C25 | −59.1 (5) | C13—C14—C15—O6 | 100.1 (4) |
C11—C5—C6—C14 | −43.7 (4) | C6—C14—C15—O6 | −102.3 (4) |
C4—C5—C6—C14 | 179.9 (3) | O6—C14—C15—C16 | −105.8 (4) |
C25—C6—C7—O5 | −110.5 (5) | C13—C14—C15—C16 | −5.7 (5) |
C14—C6—C7—O5 | 8.8 (6) | C6—C14—C15—C16 | 151.9 (4) |
C5—C6—C7—O5 | 126.0 (5) | C17—O7—C16—O8 | −178.9 (4) |
C25—C6—C7—C8 | 70.6 (4) | C17—O7—C16—C15 | 0.3 (6) |
C14—C6—C7—C8 | −170.1 (3) | O6—C15—C16—O8 | 135.0 (4) |
C5—C6—C7—C8 | −53.0 (4) | C14—C15—C16—O8 | −156.5 (4) |
O5—C7—C8—C9 | −124.5 (5) | O6—C15—C16—O7 | −44.2 (6) |
C6—C7—C8—C9 | 54.5 (5) | C14—C15—C16—O7 | 24.3 (6) |
C7—C8—C9—C10 | 172.1 (4) | C16—O7—C17—C18 | −165.1 (4) |
C7—C8—C9—C4 | −53.7 (5) | C16—O7—C17—C13 | −41.0 (5) |
C3—C4—C9—C10 | −62.6 (4) | C14—C13—C17—O7 | 54.4 (4) |
C24—C4—C9—C10 | 58.3 (5) | C28—C13—C17—O7 | −64.5 (4) |
C5—C4—C9—C10 | −177.7 (3) | C12—C13—C17—O7 | 171.2 (3) |
C3—C4—C9—C8 | 168.4 (3) | C14—C13—C17—C18 | 173.3 (4) |
C24—C4—C9—C8 | −70.7 (4) | C28—C13—C17—C18 | 54.5 (5) |
C5—C4—C9—C8 | 53.2 (4) | C12—C13—C17—C18 | −69.9 (5) |
C1—O1—C10—C27 | 65.8 (5) | O7—C17—C18—C19 | 5.5 (7) |
C1—O1—C10—C26 | 179.1 (4) | C13—C17—C18—C19 | −117.6 (6) |
C1—O1—C10—C9 | −64.4 (6) | O7—C17—C18—C21 | −174.0 (5) |
C8—C9—C10—O1 | −152.5 (4) | C13—C17—C18—C21 | 62.9 (7) |
C4—C9—C10—O1 | 77.6 (5) | C21—C18—C19—O9 | −0.1 (7) |
C8—C9—C10—C27 | 82.2 (5) | C17—C18—C19—O9 | −179.7 (5) |
C4—C9—C10—C27 | −47.7 (5) | C20—O9—C19—C18 | −0.3 (8) |
C8—C9—C10—C26 | −44.3 (5) | C19—O9—C20—C21 | 0.6 (8) |
C4—C9—C10—C26 | −174.2 (4) | O9—C20—C21—C18 | −0.7 (7) |
C4—C5—C11—C12 | −149.7 (4) | C19—C18—C21—C20 | 0.5 (7) |
C6—C5—C11—C12 | 75.1 (4) | C17—C18—C21—C20 | −179.9 (5) |
C5—C11—C12—C13 | −38.3 (5) | C3—O3—C22—O4 | −2.4 (7) |
C11—C12—C13—C14 | −22.0 (5) | C3—O3—C22—C23 | 175.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24C···O5i | 0.96 | 2.76 | 3.657 (6) | 155 |
C11—H11B···O8i | 0.97 | 2.67 | 3.274 (6) | 120 |
C20—H20A···O2ii | 0.93 | 2.57 | 3.489 (8) | 168 |
C17—H17A···O8iii | 0.98 | 2.59 | 3.374 (6) | 137 |
Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, −z+1; (iii) x−1/2, −y+3/2, −z+1. |