Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801004457/cv6010sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801004457/cv6010Isup2.hkl |
CCDC reference: 162825
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.016 Å
- R factor = 0.063
- wR factor = 0.239
- Data-to-parameter ratio = 7.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.081 Value of mu given = 0.080 STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack 0.000 From the CIF: _refine_ls_abs_structure_Flack_su 4.000 Alert C Flack test results are meaningless. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 3990 Count of symmetry unique reflns 4003 Completeness (_total/calc) 99.68% 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 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.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
The Weiss–Cook reaction (Yang-Lau et al., 1976) between acenaphthoquinone, (I), and 1,3-acetonedicarboxylate, (II), led to diketone (III), which was purified by flash chromatography (SiO2, 9:1 CH2Cl2/ethyl acetate) and recrystallized to give 62% yield, characterized by 1H and 13C NMR and CH analysis (Simion, 1996). Reaction of (III) with two equivalents of (-)-(2R,3R)-butane-2,3-diol, (IV) (toluene, reflux, PTSA cat. Dean–Stark trap), for 48 h gave the bis-ketal (V), which was purified by flash chromatography (SiO2, 1:1 benzene/ethyl acetate) and recrystallized (pentane); 80% yield, m.p. 360 K, [α]23D = -1.3° (c = 0.097, CHCl3).
The space group, P21, was determined from the systematic absences, packing considerations, a statistical analysis of intensity distribution, and the successful solution and refinement of the structure. Most of the H atoms were located from difference maps. All the H atoms were included at geometrically idealized positions with C—H = 0.95–1.00 Å, in a riding mode with isotropic displacement parameters 1.2 (non-methyl) and 1.5 (methyl) times the thermal displacement parameters of the atoms to which they were attached. An absolute structure was not established in this analysis, since the absolute configuration of the starting material was already known. There is a pseudocentre of symmetry located at 0.724, 0.702, -0.011 relating some of the atoms of the two molecules in the asymmetric unit.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1994); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN; software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C26H30O4 | F(000) = 872 |
Mr = 406.50 | Dx = 1.222 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
a = 8.1172 (11) Å | Cell parameters from 25 reflections |
b = 22.523 (4) Å | θ = 10.0–15.0° |
c = 12.5352 (13) Å | µ = 0.08 mm−1 |
β = 105.362 (12)° | T = 200 K |
V = 2209.9 (5) Å3 | Prism, colourless |
Z = 4 | 0.50 × 0.40 × 0.32 mm |
Rigaku AFC-6S diffractometer | Rint = 0.05 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.5° |
Graphite monochromator | h = 0→9 |
ω/2θ scans | k = 0→26 |
4276 measured reflections | l = −14→14 |
3990 independent reflections | 3 standard reflections every 200 reflections |
2388 reflections with I > 2σ(I) | intensity decay: <0.1% |
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)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.239 | w = 1/[σ2(Fo2) + (0.0563P)2 + 10.0719P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3990 reflections | Δρmax = 0.47 e Å−3 |
549 parameters | Δρmin = −0.52 e Å−3 |
1 restraint | Absolute structure: (Flack, 1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (4) |
C26H30O4 | V = 2209.9 (5) Å3 |
Mr = 406.50 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.1172 (11) Å | µ = 0.08 mm−1 |
b = 22.523 (4) Å | T = 200 K |
c = 12.5352 (13) Å | 0.50 × 0.40 × 0.32 mm |
β = 105.362 (12)° |
Rigaku AFC-6S diffractometer | Rint = 0.05 |
4276 measured reflections | 3 standard reflections every 200 reflections |
3990 independent reflections | intensity decay: <0.1% |
2388 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.239 | w = 1/[σ2(Fo2) + (0.0563P)2 + 10.0719P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | Δρmax = 0.47 e Å−3 |
3990 reflections | Δρmin = −0.52 e Å−3 |
549 parameters | Absolute structure: (Flack, 1983) |
1 restraint | Absolute structure parameter: 0 (4) |
x | y | z | Uiso*/Ueq | ||
O1A | 0.6601 (9) | 0.6057 (4) | 0.5693 (6) | 0.043 (2) | |
O2A | 0.7519 (9) | 0.5093 (4) | 0.5993 (6) | 0.042 (2) | |
O3A | 0.3773 (9) | 0.6959 (4) | 0.8571 (6) | 0.041 (2) | |
O4A | 0.4220 (9) | 0.7458 (4) | 0.7120 (6) | 0.042 (2) | |
C1A | 0.4957 (11) | 0.5518 (5) | 0.9261 (8) | 0.027 (2) | |
C2A | 0.3754 (12) | 0.5512 (5) | 0.8210 (8) | 0.029 (2) | |
C3A | 0.2213 (13) | 0.5253 (6) | 0.8104 (9) | 0.036 (3) | |
H3A | 0.1372 | 0.5258 | 0.7413 | 0.043* | |
C4A | 0.1872 (14) | 0.4974 (6) | 0.9041 (9) | 0.041 (3) | |
H4A | 0.0808 | 0.4780 | 0.8964 | 0.049* | |
C5A | 0.3059 (14) | 0.4981 (6) | 1.0061 (9) | 0.044 (3) | |
H5A | 0.2779 | 0.4803 | 1.0678 | 0.052* | |
C6A | 0.4647 (13) | 0.5241 (5) | 1.0201 (8) | 0.035 (3) | |
C7A | 0.6014 (15) | 0.5303 (6) | 1.1187 (9) | 0.041 (3) | |
H7A | 0.5891 | 0.5133 | 1.1855 | 0.049* | |
C8A | 0.7445 (14) | 0.5591 (6) | 1.1199 (8) | 0.040 (3) | |
H8A | 0.8327 | 0.5610 | 1.1870 | 0.048* | |
C9A | 0.7703 (12) | 0.5873 (6) | 1.0235 (9) | 0.039 (3) | |
H9A | 0.8736 | 0.6080 | 1.0267 | 0.046* | |
C10A | 0.6446 (11) | 0.5842 (5) | 0.9270 (8) | 0.029 (2) | |
C11A | 0.6374 (11) | 0.6049 (5) | 0.8119 (8) | 0.027 (2) | |
C12A | 0.4540 (11) | 0.5823 (5) | 0.7382 (8) | 0.029 (2) | |
C13A | 0.4914 (12) | 0.5408 (5) | 0.6517 (8) | 0.035 (3) | |
H13A | 0.4064 | 0.5464 | 0.5795 | 0.042* | |
H13B | 0.4878 | 0.4989 | 0.6748 | 0.042* | |
C14A | 0.6696 (13) | 0.5570 (5) | 0.6433 (8) | 0.033 (2) | |
C15A | 0.7672 (12) | 0.5728 (5) | 0.7614 (8) | 0.034 (3) | |
H15A | 0.8650 | 0.5991 | 0.7616 | 0.041* | |
H15B | 0.8109 | 0.5365 | 0.8041 | 0.041* | |
C16A | 0.6343 (12) | 0.6735 (5) | 0.7988 (9) | 0.032 (2) | |
H16A | 0.6915 | 0.6929 | 0.8698 | 0.038* | |
H16B | 0.6925 | 0.6857 | 0.7422 | 0.038* | |
C17A | 0.4451 (12) | 0.6901 (6) | 0.7628 (8) | 0.033 (3) | |
C18A | 0.3608 (12) | 0.6399 (6) | 0.6863 (8) | 0.037 (3) | |
H18A | 0.3741 | 0.6461 | 0.6109 | 0.045* | |
H18B | 0.2374 | 0.6377 | 0.6821 | 0.045* | |
C19A | 0.7947 (13) | 0.5967 (6) | 0.5146 (9) | 0.040 (3) | |
H19A | 0.9071 | 0.6071 | 0.5668 | 0.048* | |
C20A | 0.7845 (14) | 0.5308 (6) | 0.4984 (9) | 0.043 (3) | |
H20A | 0.6823 | 0.5218 | 0.4359 | 0.052* | |
C21A | 0.7666 (15) | 0.6345 (6) | 0.4135 (9) | 0.041 (3) | |
H21A | 0.7381 | 0.6750 | 0.4309 | 0.062* | |
H21B | 0.6724 | 0.6181 | 0.3551 | 0.062* | |
H21C | 0.8709 | 0.6351 | 0.3881 | 0.062* | |
C22A | 0.9378 (16) | 0.4994 (7) | 0.4765 (11) | 0.059 (4) | |
H22A | 0.9308 | 0.4568 | 0.4907 | 0.088* | |
H22B | 1.0430 | 0.5156 | 0.5255 | 0.088* | |
H22C | 0.9386 | 0.5055 | 0.3993 | 0.088* | |
C23A | 0.2543 (12) | 0.7421 (6) | 0.8358 (9) | 0.042 (3) | |
H23A | 0.2924 | 0.7737 | 0.8932 | 0.050* | |
C24A | 0.2593 (13) | 0.7674 (6) | 0.7240 (10) | 0.046 (3) | |
H24A | 0.1646 | 0.7496 | 0.6648 | 0.055* | |
C25A | 0.0789 (13) | 0.7206 (7) | 0.8399 (12) | 0.065 (4) | |
H25A | 0.0873 | 0.7013 | 0.9113 | 0.098* | |
H25B | 0.0355 | 0.6920 | 0.7800 | 0.098* | |
H25C | 0.0006 | 0.7544 | 0.8312 | 0.098* | |
C26A | 0.2541 (17) | 0.8336 (8) | 0.7124 (13) | 0.075 (5) | |
H26A | 0.2566 | 0.8444 | 0.6371 | 0.113* | |
H26B | 0.3533 | 0.8510 | 0.7655 | 0.113* | |
H26C | 0.1490 | 0.8488 | 0.7269 | 0.113* | |
O1B | 0.7745 (9) | 0.7946 (4) | 1.4027 (6) | 0.042 (2) | |
O2B | 0.6671 (10) | 0.8896 (4) | 1.3713 (6) | 0.047 (2) | |
O3B | 1.1294 (9) | 0.7188 (4) | 1.1486 (6) | 0.0375 (18) | |
O4B | 1.0682 (9) | 0.6634 (4) | 1.2840 (6) | 0.0382 (19) | |
C1B | 0.9855 (12) | 0.8542 (5) | 1.0664 (8) | 0.031 (2) | |
C2B | 0.8361 (12) | 0.8237 (5) | 1.0578 (8) | 0.030 (2) | |
C3B | 0.7173 (12) | 0.8183 (6) | 0.9557 (8) | 0.038 (3) | |
H3B | 0.6132 | 0.7973 | 0.9479 | 0.045* | |
C4B | 0.7562 (15) | 0.8448 (6) | 0.8657 (9) | 0.044 (3) | |
H4B | 0.6764 | 0.8412 | 0.7953 | 0.053* | |
C5B | 0.9031 (15) | 0.8758 (6) | 0.8729 (9) | 0.044 (3) | |
H5B | 0.9225 | 0.8938 | 0.8087 | 0.052* | |
C6B | 1.0305 (13) | 0.8813 (5) | 0.9792 (8) | 0.033 (3) | |
C7B | 1.1854 (15) | 0.9122 (7) | 1.0013 (10) | 0.051 (3) | |
H7B | 1.2195 | 0.9317 | 0.9434 | 0.061* | |
C8B | 1.2871 (14) | 0.9139 (6) | 1.1075 (11) | 0.050 (3) | |
H8B | 1.3941 | 0.9337 | 1.1211 | 0.060* | |
C9B | 1.2418 (13) | 0.8883 (6) | 1.1967 (10) | 0.041 (3) | |
H9B | 1.3136 | 0.8924 | 1.2696 | 0.049* | |
C10B | 1.0916 (12) | 0.8569 (5) | 1.1776 (8) | 0.032 (2) | |
C11B | 1.0018 (12) | 0.8261 (5) | 1.2527 (8) | 0.030 (2) | |
C12B | 0.8307 (12) | 0.7992 (5) | 1.1705 (8) | 0.029 (2) | |
C13B | 0.6837 (13) | 0.8255 (6) | 1.2124 (8) | 0.037 (3) | |
H13C | 0.6322 | 0.8600 | 1.1669 | 0.045* | |
H13D | 0.5938 | 0.7953 | 1.2093 | 0.045* | |
C14B | 0.7645 (13) | 0.8443 (5) | 1.3311 (8) | 0.037 (3) | |
C15B | 0.9406 (13) | 0.8680 (6) | 1.3312 (8) | 0.040 (3) | |
H15C | 1.0192 | 0.8667 | 1.4065 | 0.048* | |
H15D | 0.9330 | 0.9094 | 1.3038 | 0.048* | |
C16B | 1.0984 (13) | 0.7706 (6) | 1.3120 (8) | 0.039 (3) | |
H16C | 1.2236 | 0.7760 | 1.3274 | 0.046* | |
H16D | 1.0691 | 0.7629 | 1.3825 | 0.046* | |
C17B | 1.0382 (12) | 0.7203 (6) | 1.2313 (8) | 0.035 (3) | |
C18B | 0.8486 (12) | 0.7322 (5) | 1.1816 (9) | 0.034 (3) | |
H18C | 0.8084 | 0.7129 | 1.1083 | 0.041* | |
H18D | 0.7808 | 0.7167 | 1.2306 | 0.041* | |
C19B | 0.7526 (14) | 0.8178 (6) | 1.5039 (8) | 0.040 (3) | |
H19B | 0.8619 | 0.8361 | 1.5476 | 0.047* | |
C20B | 0.6218 (14) | 0.8648 (6) | 1.4661 (8) | 0.044 (3) | |
H20B | 0.5056 | 0.8465 | 1.4422 | 0.053* | |
C21B | 0.703 (2) | 0.7680 (7) | 1.5691 (11) | 0.068 (4) | |
H21D | 0.7945 | 0.7384 | 1.5871 | 0.102* | |
H21E | 0.5976 | 0.7493 | 1.5250 | 0.102* | |
H21F | 0.6833 | 0.7838 | 1.6376 | 0.102* | |
C22B | 0.6209 (19) | 0.9145 (7) | 1.5449 (11) | 0.066 (4) | |
H22D | 0.5367 | 0.9443 | 1.5088 | 0.099* | |
H22E | 0.7345 | 0.9326 | 1.5673 | 0.099* | |
H22F | 0.5908 | 0.8990 | 1.6104 | 0.099* | |
C23B | 1.2745 (13) | 0.6818 (6) | 1.1931 (9) | 0.042 (3) | |
H23B | 1.3569 | 0.7034 | 1.2543 | 0.050* | |
C24B | 1.1907 (13) | 0.6323 (6) | 1.2415 (9) | 0.044 (3) | |
H24B | 1.1286 | 0.6056 | 1.1802 | 0.052* | |
C25B | 1.3598 (16) | 0.6670 (7) | 1.1047 (10) | 0.057 (4) | |
H25D | 1.3923 | 0.7037 | 1.0736 | 0.085* | |
H25E | 1.2810 | 0.6443 | 1.0461 | 0.085* | |
H25F | 1.4623 | 0.6432 | 1.1363 | 0.085* | |
C26B | 1.3017 (16) | 0.5952 (7) | 1.3310 (11) | 0.063 (4) | |
H26D | 1.2302 | 0.5724 | 1.3680 | 0.094* | |
H26E | 1.3786 | 0.6211 | 1.3849 | 0.094* | |
H26F | 1.3693 | 0.5680 | 1.2987 | 0.094* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.040 (4) | 0.064 (6) | 0.035 (4) | 0.011 (4) | 0.026 (3) | 0.009 (4) |
O2A | 0.052 (4) | 0.046 (5) | 0.040 (4) | 0.018 (4) | 0.031 (4) | 0.012 (4) |
O3A | 0.032 (4) | 0.059 (6) | 0.038 (4) | 0.005 (4) | 0.019 (3) | −0.005 (4) |
O4A | 0.033 (4) | 0.042 (5) | 0.055 (5) | 0.016 (4) | 0.019 (4) | 0.014 (4) |
C1A | 0.024 (5) | 0.033 (6) | 0.026 (5) | −0.001 (4) | 0.008 (4) | −0.001 (5) |
C2A | 0.028 (5) | 0.036 (7) | 0.025 (5) | 0.003 (5) | 0.010 (4) | 0.001 (5) |
C3A | 0.030 (5) | 0.046 (8) | 0.032 (5) | −0.011 (5) | 0.007 (4) | −0.004 (5) |
C4A | 0.036 (6) | 0.044 (8) | 0.048 (7) | −0.012 (5) | 0.023 (5) | 0.000 (6) |
C5A | 0.053 (7) | 0.049 (9) | 0.039 (6) | −0.011 (6) | 0.029 (6) | 0.006 (6) |
C6A | 0.041 (6) | 0.036 (7) | 0.035 (6) | 0.002 (5) | 0.020 (5) | 0.001 (5) |
C7A | 0.056 (7) | 0.043 (8) | 0.029 (6) | 0.010 (6) | 0.021 (5) | 0.006 (5) |
C8A | 0.044 (6) | 0.054 (8) | 0.021 (5) | 0.010 (6) | 0.005 (5) | 0.001 (5) |
C9A | 0.029 (5) | 0.049 (8) | 0.035 (6) | −0.004 (5) | 0.005 (4) | −0.001 (5) |
C10A | 0.025 (5) | 0.038 (7) | 0.026 (5) | 0.007 (5) | 0.009 (4) | −0.004 (5) |
C11A | 0.023 (4) | 0.035 (7) | 0.024 (5) | −0.003 (4) | 0.011 (4) | 0.004 (4) |
C12A | 0.023 (4) | 0.038 (7) | 0.025 (5) | −0.005 (5) | 0.005 (4) | −0.002 (5) |
C13A | 0.036 (5) | 0.045 (7) | 0.027 (5) | −0.005 (5) | 0.015 (4) | −0.002 (5) |
C14A | 0.042 (6) | 0.033 (6) | 0.029 (5) | −0.004 (5) | 0.018 (5) | −0.009 (5) |
C15A | 0.026 (5) | 0.048 (7) | 0.031 (5) | 0.009 (5) | 0.013 (4) | 0.004 (5) |
C16A | 0.024 (5) | 0.038 (7) | 0.032 (5) | 0.004 (5) | 0.007 (4) | 0.004 (5) |
C17A | 0.021 (5) | 0.051 (8) | 0.031 (5) | 0.009 (5) | 0.011 (4) | 0.004 (5) |
C18A | 0.026 (5) | 0.056 (8) | 0.028 (5) | 0.003 (5) | 0.005 (4) | 0.005 (5) |
C19A | 0.037 (5) | 0.053 (8) | 0.034 (6) | 0.010 (5) | 0.019 (5) | −0.002 (5) |
C20A | 0.049 (6) | 0.056 (8) | 0.032 (6) | 0.017 (6) | 0.023 (5) | 0.012 (6) |
C21A | 0.059 (7) | 0.033 (7) | 0.039 (6) | 0.002 (6) | 0.027 (5) | 0.004 (5) |
C22A | 0.066 (8) | 0.071 (11) | 0.053 (8) | 0.022 (7) | 0.039 (7) | −0.001 (7) |
C23A | 0.025 (5) | 0.055 (8) | 0.047 (6) | 0.001 (5) | 0.012 (5) | −0.002 (6) |
C24A | 0.029 (5) | 0.055 (8) | 0.056 (7) | 0.019 (5) | 0.015 (5) | 0.018 (6) |
C25A | 0.028 (6) | 0.093 (12) | 0.080 (9) | 0.017 (7) | 0.024 (6) | 0.033 (9) |
C26A | 0.051 (8) | 0.089 (13) | 0.093 (11) | 0.027 (8) | 0.032 (8) | 0.029 (10) |
O1B | 0.055 (5) | 0.044 (5) | 0.036 (4) | 0.017 (4) | 0.028 (4) | 0.013 (4) |
O2B | 0.062 (5) | 0.055 (6) | 0.037 (4) | 0.028 (4) | 0.035 (4) | 0.010 (4) |
O3B | 0.037 (4) | 0.045 (5) | 0.037 (4) | 0.006 (4) | 0.021 (3) | 0.005 (4) |
O4B | 0.046 (4) | 0.032 (5) | 0.044 (4) | −0.004 (4) | 0.024 (3) | 0.004 (4) |
C1B | 0.031 (5) | 0.037 (7) | 0.027 (5) | 0.009 (5) | 0.011 (4) | −0.005 (5) |
C2B | 0.030 (5) | 0.032 (6) | 0.028 (5) | −0.003 (5) | 0.010 (4) | −0.005 (5) |
C3B | 0.027 (5) | 0.054 (8) | 0.031 (5) | 0.004 (5) | 0.006 (4) | −0.011 (5) |
C4B | 0.050 (7) | 0.051 (8) | 0.028 (6) | 0.014 (6) | 0.003 (5) | −0.005 (5) |
C5B | 0.056 (7) | 0.052 (9) | 0.032 (6) | 0.014 (6) | 0.027 (5) | 0.000 (6) |
C6B | 0.041 (6) | 0.029 (7) | 0.035 (6) | 0.009 (5) | 0.018 (5) | 0.005 (5) |
C7B | 0.047 (7) | 0.064 (10) | 0.054 (8) | 0.007 (7) | 0.035 (6) | 0.004 (7) |
C8B | 0.032 (6) | 0.045 (8) | 0.079 (9) | 0.003 (5) | 0.025 (6) | 0.009 (7) |
C9B | 0.028 (5) | 0.044 (8) | 0.048 (7) | −0.008 (5) | 0.006 (5) | −0.006 (6) |
C10B | 0.027 (5) | 0.041 (7) | 0.027 (5) | 0.010 (5) | 0.008 (4) | −0.004 (5) |
C11B | 0.031 (5) | 0.034 (7) | 0.026 (5) | −0.011 (5) | 0.009 (4) | −0.002 (5) |
C12B | 0.025 (5) | 0.033 (6) | 0.030 (5) | 0.006 (4) | 0.011 (4) | 0.000 (5) |
C13B | 0.040 (6) | 0.045 (7) | 0.031 (5) | 0.017 (5) | 0.017 (5) | 0.009 (5) |
C14B | 0.044 (6) | 0.038 (7) | 0.034 (6) | 0.007 (5) | 0.019 (5) | 0.004 (5) |
C15B | 0.042 (6) | 0.052 (8) | 0.029 (5) | 0.009 (6) | 0.014 (5) | 0.000 (5) |
C16B | 0.033 (5) | 0.058 (8) | 0.026 (5) | 0.007 (5) | 0.009 (4) | 0.005 (5) |
C17B | 0.029 (5) | 0.053 (8) | 0.031 (5) | 0.012 (5) | 0.019 (4) | 0.020 (6) |
C18B | 0.034 (5) | 0.038 (7) | 0.035 (5) | 0.000 (5) | 0.016 (4) | 0.006 (5) |
C19B | 0.052 (7) | 0.042 (7) | 0.032 (6) | 0.008 (6) | 0.024 (5) | 0.005 (5) |
C20B | 0.047 (6) | 0.061 (8) | 0.033 (6) | 0.008 (6) | 0.028 (5) | 0.007 (6) |
C21B | 0.115 (12) | 0.053 (10) | 0.056 (8) | 0.011 (9) | 0.057 (8) | 0.009 (7) |
C22B | 0.099 (11) | 0.064 (10) | 0.049 (7) | 0.029 (9) | 0.042 (8) | 0.021 (7) |
C23B | 0.031 (5) | 0.064 (9) | 0.031 (5) | 0.009 (5) | 0.011 (5) | 0.001 (5) |
C24B | 0.032 (5) | 0.056 (8) | 0.042 (6) | 0.018 (6) | 0.009 (5) | 0.007 (6) |
C25B | 0.053 (7) | 0.072 (10) | 0.054 (8) | 0.013 (7) | 0.029 (6) | −0.005 (7) |
C26B | 0.049 (7) | 0.076 (11) | 0.066 (8) | 0.022 (7) | 0.020 (6) | 0.024 (8) |
O1A—C14A | 1.424 (14) | O1B—C14B | 1.423 (14) |
O1A—C19A | 1.450 (11) | O1B—C19B | 1.426 (12) |
O2A—C20A | 1.442 (12) | O2B—C20B | 1.446 (12) |
O2A—C14A | 1.450 (13) | O2B—C14B | 1.460 (13) |
O3A—C23A | 1.417 (14) | O3B—C17B | 1.425 (11) |
O3A—C17A | 1.437 (12) | O3B—C23B | 1.431 (13) |
O4A—C17A | 1.396 (14) | O4B—C24B | 1.429 (13) |
O4A—C24A | 1.452 (12) | O4B—C17B | 1.433 (14) |
C1A—C10A | 1.409 (14) | C1B—C2B | 1.372 (14) |
C1A—C6A | 1.414 (14) | C1B—C6B | 1.384 (14) |
C1A—C2A | 1.417 (13) | C1B—C10B | 1.433 (14) |
C2A—C3A | 1.354 (14) | C2B—C3B | 1.389 (14) |
C2A—C12A | 1.526 (14) | C2B—C12B | 1.528 (14) |
C3A—C4A | 1.422 (16) | C3B—C4B | 1.384 (17) |
C3A—H3A | 0.9500 | C3B—H3B | 0.9500 |
C4A—C5A | 1.382 (16) | C4B—C5B | 1.365 (17) |
C4A—H4A | 0.9500 | C4B—H4B | 0.9500 |
C5A—C6A | 1.384 (15) | C5B—C6B | 1.459 (15) |
C5A—H5A | 0.9500 | C5B—H5B | 0.9500 |
C6A—C7A | 1.432 (15) | C6B—C7B | 1.400 (16) |
C7A—C8A | 1.327 (17) | C7B—C8B | 1.369 (17) |
C7A—H7A | 0.9500 | C7B—H7B | 0.9500 |
C8A—C9A | 1.429 (16) | C8B—C9B | 1.391 (17) |
C8A—H8A | 0.9500 | C8B—H8B | 0.9500 |
C9A—C10A | 1.362 (13) | C9B—C10B | 1.374 (15) |
C9A—H9A | 0.9500 | C9B—H9B | 0.9500 |
C10A—C11A | 1.503 (13) | C10B—C11B | 1.503 (14) |
C11A—C15A | 1.545 (13) | C11B—C15B | 1.537 (15) |
C11A—C16A | 1.554 (16) | C11B—C16B | 1.557 (16) |
C11A—C12A | 1.613 (12) | C11B—C12B | 1.612 (13) |
C12A—C13A | 1.521 (14) | C12B—C18B | 1.518 (16) |
C12A—C18A | 1.556 (16) | C12B—C13B | 1.543 (13) |
C13A—C14A | 1.523 (13) | C13B—C14B | 1.518 (14) |
C13A—H13A | 0.9900 | C13B—H13C | 0.9900 |
C13A—H13B | 0.9900 | C13B—H13D | 0.9900 |
C14A—C15A | 1.524 (13) | C14B—C15B | 1.526 (15) |
C15A—H15A | 0.9900 | C15B—H15C | 0.9900 |
C15A—H15B | 0.9900 | C15B—H15D | 0.9900 |
C16A—C17A | 1.527 (13) | C16B—C17B | 1.510 (17) |
C16A—H16A | 0.9900 | C16B—H16C | 0.9900 |
C16A—H16B | 0.9900 | C16B—H16D | 0.9900 |
C17A—C18A | 1.522 (17) | C17B—C18B | 1.524 (13) |
C18A—H18A | 0.9900 | C18B—H18C | 0.9900 |
C18A—H18B | 0.9900 | C18B—H18D | 0.9900 |
C19A—C21A | 1.493 (15) | C19B—C20B | 1.486 (15) |
C19A—C20A | 1.497 (18) | C19B—C21B | 1.506 (18) |
C19A—H19A | 1.0000 | C19B—H19B | 1.0000 |
C20A—C22A | 1.519 (15) | C20B—C22B | 1.493 (18) |
C20A—H20A | 1.0000 | C20B—H20B | 1.0000 |
C21A—H21A | 0.9800 | C21B—H21D | 0.9800 |
C21A—H21B | 0.9800 | C21B—H21E | 0.9800 |
C21A—H21C | 0.9800 | C21B—H21F | 0.9800 |
C22A—H22A | 0.9800 | C22B—H22D | 0.9800 |
C22A—H22B | 0.9800 | C22B—H22E | 0.9800 |
C22A—H22C | 0.9800 | C22B—H22F | 0.9800 |
C23A—C25A | 1.518 (15) | C23B—C25B | 1.492 (15) |
C23A—C24A | 1.524 (16) | C23B—C24B | 1.514 (18) |
C23A—H23A | 1.0000 | C23B—H23B | 1.0000 |
C24A—C26A | 1.50 (2) | C24B—C26B | 1.493 (16) |
C24A—H24A | 1.0000 | C24B—H24B | 1.0000 |
C25A—H25A | 0.9800 | C25B—H25D | 0.9800 |
C25A—H25B | 0.9800 | C25B—H25E | 0.9800 |
C25A—H25C | 0.9800 | C25B—H25F | 0.9800 |
C26A—H26A | 0.9800 | C26B—H26D | 0.9800 |
C26A—H26B | 0.9800 | C26B—H26E | 0.9800 |
C26A—H26C | 0.9800 | C26B—H26F | 0.9800 |
C14A—O1A—C19A | 106.4 (8) | C14B—O1B—C19B | 105.9 (8) |
C20A—O2A—C14A | 107.1 (8) | C20B—O2B—C14B | 107.1 (8) |
C23A—O3A—C17A | 108.4 (8) | C17B—O3B—C23B | 105.2 (7) |
C17A—O4A—C24A | 105.7 (8) | C24B—O4B—C17B | 108.5 (8) |
C10A—C1A—C6A | 124.3 (9) | C2B—C1B—C6B | 124.9 (9) |
C10A—C1A—C2A | 113.0 (9) | C2B—C1B—C10B | 112.9 (9) |
C6A—C1A—C2A | 122.7 (9) | C6B—C1B—C10B | 122.2 (10) |
C3A—C2A—C1A | 119.1 (9) | C1B—C2B—C3B | 119.9 (10) |
C3A—C2A—C12A | 132.3 (9) | C1B—C2B—C12B | 110.4 (8) |
C1A—C2A—C12A | 108.6 (8) | C3B—C2B—C12B | 129.6 (10) |
C2A—C3A—C4A | 119.1 (10) | C4B—C3B—C2B | 117.5 (10) |
C2A—C3A—H3A | 120.5 | C4B—C3B—H3B | 121.3 |
C4A—C3A—H3A | 120.5 | C2B—C3B—H3B | 121.3 |
C5A—C4A—C3A | 121.2 (10) | C5B—C4B—C3B | 123.4 (10) |
C5A—C4A—H4A | 119.4 | C5B—C4B—H4B | 118.3 |
C3A—C4A—H4A | 119.4 | C3B—C4B—H4B | 118.3 |
C4A—C5A—C6A | 121.3 (10) | C4B—C5B—C6B | 119.9 (11) |
C4A—C5A—H5A | 119.3 | C4B—C5B—H5B | 120.0 |
C6A—C5A—H5A | 119.3 | C6B—C5B—H5B | 120.0 |
C5A—C6A—C1A | 116.5 (10) | C1B—C6B—C7B | 118.3 (10) |
C5A—C6A—C7A | 129.3 (10) | C1B—C6B—C5B | 114.4 (10) |
C1A—C6A—C7A | 114.1 (9) | C7B—C6B—C5B | 127.2 (11) |
C8A—C7A—C6A | 122.2 (11) | C8B—C7B—C6B | 119.1 (12) |
C8A—C7A—H7A | 118.9 | C8B—C7B—H7B | 120.5 |
C6A—C7A—H7A | 118.9 | C6B—C7B—H7B | 120.5 |
C7A—C8A—C9A | 122.2 (10) | C7B—C8B—C9B | 123.4 (11) |
C7A—C8A—H8A | 118.9 | C7B—C8B—H8B | 118.3 |
C9A—C8A—H8A | 118.9 | C9B—C8B—H8B | 118.3 |
C10A—C9A—C8A | 118.9 (10) | C10B—C9B—C8B | 119.0 (10) |
C10A—C9A—H9A | 120.5 | C10B—C9B—H9B | 120.5 |
C8A—C9A—H9A | 120.5 | C8B—C9B—H9B | 120.5 |
C9A—C10A—C1A | 118.3 (10) | C9B—C10B—C1B | 117.9 (10) |
C9A—C10A—C11A | 131.7 (9) | C9B—C10B—C11B | 133.1 (9) |
C1A—C10A—C11A | 109.7 (8) | C1B—C10B—C11B | 108.8 (9) |
C10A—C11A—C15A | 113.0 (8) | C10B—C11B—C15B | 114.2 (10) |
C10A—C11A—C16A | 113.9 (9) | C10B—C11B—C16B | 113.7 (8) |
C15A—C11A—C16A | 114.6 (9) | C15B—C11B—C16B | 113.2 (8) |
C10A—C11A—C12A | 104.3 (8) | C10B—C11B—C12B | 104.6 (8) |
C15A—C11A—C12A | 104.1 (8) | C15B—C11B—C12B | 105.7 (8) |
C16A—C11A—C12A | 105.4 (8) | C16B—C11B—C12B | 104.0 (9) |
C13A—C12A—C2A | 113.7 (9) | C18B—C12B—C2B | 114.7 (9) |
C13A—C12A—C18A | 112.5 (8) | C18B—C12B—C13B | 114.4 (9) |
C2A—C12A—C18A | 115.0 (8) | C2B—C12B—C13B | 113.0 (8) |
C13A—C12A—C11A | 105.9 (7) | C18B—C12B—C11B | 105.7 (8) |
C2A—C12A—C11A | 104.1 (7) | C2B—C12B—C11B | 102.9 (8) |
C18A—C12A—C11A | 104.4 (9) | C13B—C12B—C11B | 104.5 (8) |
C12A—C13A—C14A | 105.9 (8) | C14B—C13B—C12B | 105.6 (8) |
C12A—C13A—H13A | 110.6 | C14B—C13B—H13C | 110.6 |
C14A—C13A—H13A | 110.6 | C12B—C13B—H13C | 110.6 |
C12A—C13A—H13B | 110.6 | C14B—C13B—H13D | 110.6 |
C14A—C13A—H13B | 110.6 | C12B—C13B—H13D | 110.6 |
H13A—C13A—H13B | 108.7 | H13C—C13B—H13D | 108.8 |
O1A—C14A—O2A | 105.9 (7) | O1B—C14B—O2B | 106.1 (7) |
O1A—C14A—C13A | 109.9 (9) | O1B—C14B—C13B | 109.7 (10) |
O2A—C14A—C13A | 113.0 (9) | O2B—C14B—C13B | 113.6 (8) |
O1A—C14A—C15A | 112.2 (9) | O1B—C14B—C15B | 112.2 (9) |
O2A—C14A—C15A | 111.7 (8) | O2B—C14B—C15B | 110.4 (10) |
C13A—C14A—C15A | 104.3 (8) | C13B—C14B—C15B | 105.1 (8) |
C14A—C15A—C11A | 105.8 (8) | C14B—C15B—C11B | 104.3 (9) |
C14A—C15A—H15A | 110.6 | C14B—C15B—H15C | 110.9 |
C11A—C15A—H15A | 110.6 | C11B—C15B—H15C | 110.9 |
C14A—C15A—H15B | 110.6 | C14B—C15B—H15D | 110.9 |
C11A—C15A—H15B | 110.6 | C11B—C15B—H15D | 110.9 |
H15A—C15A—H15B | 108.7 | H15C—C15B—H15D | 108.9 |
C17A—C16A—C11A | 105.2 (9) | C17B—C16B—C11B | 104.5 (8) |
C17A—C16A—H16A | 110.7 | C17B—C16B—H16C | 110.9 |
C11A—C16A—H16A | 110.7 | C11B—C16B—H16C | 110.9 |
C17A—C16A—H16B | 110.7 | C17B—C16B—H16D | 110.9 |
C11A—C16A—H16B | 110.7 | C11B—C16B—H16D | 110.9 |
H16A—C16A—H16B | 108.8 | H16C—C16B—H16D | 108.9 |
O4A—C17A—O3A | 105.0 (9) | O3B—C17B—O4B | 104.9 (9) |
O4A—C17A—C18A | 113.3 (8) | O3B—C17B—C16B | 111.5 (9) |
O3A—C17A—C18A | 112.3 (9) | O4B—C17B—C16B | 112.1 (8) |
O4A—C17A—C16A | 110.9 (9) | O3B—C17B—C18B | 111.7 (8) |
O3A—C17A—C16A | 110.7 (8) | O4B—C17B—C18B | 112.0 (9) |
C18A—C17A—C16A | 104.7 (9) | C16B—C17B—C18B | 104.8 (9) |
C17A—C18A—C12A | 105.6 (8) | C12B—C18B—C17B | 105.9 (9) |
C17A—C18A—H18A | 110.6 | C12B—C18B—H18C | 110.6 |
C12A—C18A—H18A | 110.6 | C17B—C18B—H18C | 110.6 |
C17A—C18A—H18B | 110.6 | C12B—C18B—H18D | 110.6 |
C12A—C18A—H18B | 110.6 | C17B—C18B—H18D | 110.6 |
H18A—C18A—H18B | 108.8 | H18C—C18B—H18D | 108.7 |
O1A—C19A—C21A | 110.9 (9) | O1B—C19B—C20B | 103.0 (8) |
O1A—C19A—C20A | 100.4 (9) | O1B—C19B—C21B | 109.0 (11) |
C21A—C19A—C20A | 117.3 (10) | C20B—C19B—C21B | 115.6 (10) |
O1A—C19A—H19A | 109.2 | O1B—C19B—H19B | 109.7 |
C21A—C19A—H19A | 109.2 | C20B—C19B—H19B | 109.7 |
C20A—C19A—H19A | 109.2 | C21B—C19B—H19B | 109.7 |
O2A—C20A—C19A | 103.3 (9) | O2B—C20B—C19B | 102.8 (8) |
O2A—C20A—C22A | 110.6 (9) | O2B—C20B—C22B | 107.6 (11) |
C19A—C20A—C22A | 117.9 (11) | C19B—C20B—C22B | 116.8 (10) |
O2A—C20A—H20A | 108.2 | O2B—C20B—H20B | 109.8 |
C19A—C20A—H20A | 108.2 | C19B—C20B—H20B | 109.8 |
C22A—C20A—H20A | 108.2 | C22B—C20B—H20B | 109.8 |
C19A—C21A—H21A | 109.5 | C19B—C21B—H21D | 109.5 |
C19A—C21A—H21B | 109.5 | C19B—C21B—H21E | 109.5 |
H21A—C21A—H21B | 109.5 | H21D—C21B—H21E | 109.5 |
C19A—C21A—H21C | 109.5 | C19B—C21B—H21F | 109.5 |
H21A—C21A—H21C | 109.5 | H21D—C21B—H21F | 109.5 |
H21B—C21A—H21C | 109.5 | H21E—C21B—H21F | 109.5 |
C20A—C22A—H22A | 109.5 | C20B—C22B—H22D | 109.5 |
C20A—C22A—H22B | 109.5 | C20B—C22B—H22E | 109.5 |
H22A—C22A—H22B | 109.5 | H22D—C22B—H22E | 109.5 |
C20A—C22A—H22C | 109.5 | C20B—C22B—H22F | 109.5 |
H22A—C22A—H22C | 109.5 | H22D—C22B—H22F | 109.5 |
H22B—C22A—H22C | 109.5 | H22E—C22B—H22F | 109.5 |
O3A—C23A—C25A | 112.3 (11) | O3B—C23B—C25B | 109.7 (9) |
O3A—C23A—C24A | 105.0 (8) | O3B—C23B—C24B | 100.1 (8) |
C25A—C23A—C24A | 113.9 (9) | C25B—C23B—C24B | 118.7 (12) |
O3A—C23A—H23A | 108.5 | O3B—C23B—H23B | 109.3 |
C25A—C23A—H23A | 108.5 | C25B—C23B—H23B | 109.3 |
C24A—C23A—H23A | 108.5 | C24B—C23B—H23B | 109.3 |
O4A—C24A—C26A | 109.1 (10) | O4B—C24B—C26B | 109.6 (10) |
O4A—C24A—C23A | 102.5 (8) | O4B—C24B—C23B | 102.7 (10) |
C26A—C24A—C23A | 117.0 (12) | C26B—C24B—C23B | 117.8 (10) |
O4A—C24A—H24A | 109.3 | O4B—C24B—H24B | 108.8 |
C26A—C24A—H24A | 109.3 | C26B—C24B—H24B | 108.8 |
C23A—C24A—H24A | 109.3 | C23B—C24B—H24B | 108.8 |
C23A—C25A—H25A | 109.5 | C23B—C25B—H25D | 109.5 |
C23A—C25A—H25B | 109.5 | C23B—C25B—H25E | 109.5 |
H25A—C25A—H25B | 109.5 | H25D—C25B—H25E | 109.5 |
C23A—C25A—H25C | 109.5 | C23B—C25B—H25F | 109.5 |
H25A—C25A—H25C | 109.5 | H25D—C25B—H25F | 109.5 |
H25B—C25A—H25C | 109.5 | H25E—C25B—H25F | 109.5 |
C24A—C26A—H26A | 109.5 | C24B—C26B—H26D | 109.5 |
C24A—C26A—H26B | 109.5 | C24B—C26B—H26E | 109.5 |
H26A—C26A—H26B | 109.5 | H26D—C26B—H26E | 109.5 |
C24A—C26A—H26C | 109.5 | C24B—C26B—H26F | 109.5 |
H26A—C26A—H26C | 109.5 | H26D—C26B—H26F | 109.5 |
H26B—C26A—H26C | 109.5 | H26E—C26B—H26F | 109.5 |
C10A—C1A—C2A—C3A | −175.3 (10) | C6B—C1B—C2B—C3B | 0.1 (18) |
C6A—C1A—C2A—C3A | 2.9 (17) | C10B—C1B—C2B—C3B | 178.4 (10) |
C10A—C1A—C2A—C12A | 4.8 (13) | C6B—C1B—C2B—C12B | 179.4 (10) |
C6A—C1A—C2A—C12A | −177.1 (10) | C10B—C1B—C2B—C12B | −2.3 (13) |
C1A—C2A—C3A—C4A | −2.4 (17) | C1B—C2B—C3B—C4B | −0.2 (17) |
C12A—C2A—C3A—C4A | 177.5 (12) | C12B—C2B—C3B—C4B | −179.3 (11) |
C2A—C3A—C4A—C5A | 2.2 (19) | C2B—C3B—C4B—C5B | −0.6 (19) |
C3A—C4A—C5A—C6A | −2 (2) | C3B—C4B—C5B—C6B | 1.3 (19) |
C4A—C5A—C6A—C1A | 2.5 (19) | C2B—C1B—C6B—C7B | 178.3 (12) |
C4A—C5A—C6A—C7A | 178.4 (13) | C10B—C1B—C6B—C7B | 0.1 (17) |
C10A—C1A—C6A—C5A | 175.1 (11) | C2B—C1B—C6B—C5B | 0.6 (17) |
C2A—C1A—C6A—C5A | −2.8 (17) | C10B—C1B—C6B—C5B | −177.5 (10) |
C10A—C1A—C6A—C7A | −1.4 (17) | C4B—C5B—C6B—C1B | −1.3 (17) |
C2A—C1A—C6A—C7A | −179.3 (11) | C4B—C5B—C6B—C7B | −178.7 (12) |
C5A—C6A—C7A—C8A | −176.8 (13) | C1B—C6B—C7B—C8B | 0.7 (19) |
C1A—C6A—C7A—C8A | −0.8 (18) | C5B—C6B—C7B—C8B | 178.0 (12) |
C6A—C7A—C8A—C9A | 2 (2) | C6B—C7B—C8B—C9B | −3 (2) |
C7A—C8A—C9A—C10A | −0.6 (19) | C7B—C8B—C9B—C10B | 3 (2) |
C8A—C9A—C10A—C1A | −1.5 (17) | C8B—C9B—C10B—C1B | −2.4 (17) |
C8A—C9A—C10A—C11A | −175.0 (11) | C8B—C9B—C10B—C11B | −177.2 (12) |
C6A—C1A—C10A—C9A | 2.6 (17) | C2B—C1B—C10B—C9B | −177.6 (10) |
C2A—C1A—C10A—C9A | −179.3 (10) | C6B—C1B—C10B—C9B | 0.8 (17) |
C6A—C1A—C10A—C11A | 177.4 (10) | C2B—C1B—C10B—C11B | −1.6 (13) |
C2A—C1A—C10A—C11A | −4.5 (13) | C6B—C1B—C10B—C11B | 176.8 (10) |
C9A—C10A—C11A—C15A | 63.7 (17) | C9B—C10B—C11B—C15B | 64.6 (16) |
C1A—C10A—C11A—C15A | −110.2 (10) | C1B—C10B—C11B—C15B | −110.6 (10) |
C9A—C10A—C11A—C16A | −69.4 (15) | C9B—C10B—C11B—C16B | −67.5 (16) |
C1A—C10A—C11A—C16A | 116.7 (10) | C1B—C10B—C11B—C16B | 117.3 (10) |
C9A—C10A—C11A—C12A | 176.1 (12) | C9B—C10B—C11B—C12B | 179.7 (12) |
C1A—C10A—C11A—C12A | 2.3 (12) | C1B—C10B—C11B—C12B | 4.5 (12) |
C3A—C2A—C12A—C13A | −68.2 (15) | C1B—C2B—C12B—C18B | −109.4 (11) |
C1A—C2A—C12A—C13A | 111.8 (10) | C3B—C2B—C12B—C18B | 69.8 (14) |
C3A—C2A—C12A—C18A | 63.4 (16) | C1B—C2B—C12B—C13B | 117.0 (10) |
C1A—C2A—C12A—C18A | −116.6 (10) | C3B—C2B—C12B—C13B | −63.8 (16) |
C3A—C2A—C12A—C11A | 177.0 (12) | C1B—C2B—C12B—C11B | 4.8 (11) |
C1A—C2A—C12A—C11A | −3.0 (11) | C3B—C2B—C12B—C11B | −176.0 (11) |
C10A—C11A—C12A—C13A | −119.7 (9) | C10B—C11B—C12B—C18B | 115.2 (9) |
C15A—C11A—C12A—C13A | −1.0 (11) | C15B—C11B—C12B—C18B | −123.9 (9) |
C16A—C11A—C12A—C13A | 120.0 (9) | C16B—C11B—C12B—C18B | −4.4 (10) |
C10A—C11A—C12A—C2A | 0.5 (11) | C10B—C11B—C12B—C2B | −5.5 (10) |
C15A—C11A—C12A—C2A | 119.2 (9) | C15B—C11B—C12B—C2B | 115.4 (9) |
C16A—C11A—C12A—C2A | −119.9 (9) | C16B—C11B—C12B—C2B | −125.0 (8) |
C10A—C11A—C12A—C18A | 121.4 (9) | C10B—C11B—C12B—C13B | −123.7 (9) |
C15A—C11A—C12A—C18A | −119.9 (9) | C15B—C11B—C12B—C13B | −2.8 (11) |
C16A—C11A—C12A—C18A | 1.1 (10) | C16B—C11B—C12B—C13B | 116.7 (9) |
C2A—C12A—C13A—C14A | −135.1 (9) | C18B—C12B—C13B—C14B | 94.6 (11) |
C18A—C12A—C13A—C14A | 92.1 (10) | C2B—C12B—C13B—C14B | −131.7 (10) |
C11A—C12A—C13A—C14A | −21.4 (11) | C11B—C12B—C13B—C14B | −20.5 (11) |
C19A—O1A—C14A—O2A | −24.2 (11) | C19B—O1B—C14B—O2B | −23.8 (11) |
C19A—O1A—C14A—C13A | −146.5 (8) | C19B—O1B—C14B—C13B | −146.9 (8) |
C19A—O1A—C14A—C15A | 97.9 (9) | C19B—O1B—C14B—C15B | 96.8 (10) |
C20A—O2A—C14A—O1A | −1.5 (11) | C20B—O2B—C14B—O1B | −0.2 (11) |
C20A—O2A—C14A—C13A | 118.8 (10) | C20B—O2B—C14B—C13B | 120.3 (10) |
C20A—O2A—C14A—C15A | −123.9 (10) | C20B—O2B—C14B—C15B | −122.0 (9) |
C12A—C13A—C14A—O1A | −84.3 (10) | C12B—C13B—C14B—O1B | −83.9 (10) |
C12A—C13A—C14A—O2A | 157.6 (8) | C12B—C13B—C14B—O2B | 157.7 (9) |
C12A—C13A—C14A—C15A | 36.2 (11) | C12B—C13B—C14B—C15B | 36.9 (12) |
O1A—C14A—C15A—C11A | 82.1 (10) | O1B—C14B—C15B—C11B | 80.7 (10) |
O2A—C14A—C15A—C11A | −159.2 (9) | O2B—C14B—C15B—C11B | −161.3 (8) |
C13A—C14A—C15A—C11A | −36.8 (11) | C13B—C14B—C15B—C11B | −38.4 (11) |
C10A—C11A—C15A—C14A | 135.5 (9) | C10B—C11B—C15B—C14B | 139.2 (9) |
C16A—C11A—C15A—C14A | −91.7 (10) | C16B—C11B—C15B—C14B | −88.4 (10) |
C12A—C11A—C15A—C14A | 23.0 (11) | C12B—C11B—C15B—C14B | 24.8 (11) |
C10A—C11A—C16A—C17A | −92.2 (9) | C10B—C11B—C16B—C17B | −86.8 (10) |
C15A—C11A—C16A—C17A | 135.5 (8) | C15B—C11B—C16B—C17B | 140.6 (9) |
C12A—C11A—C16A—C17A | 21.6 (10) | C12B—C11B—C16B—C17B | 26.4 (10) |
C24A—O4A—C17A—O3A | −37.0 (11) | C23B—O3B—C17B—O4B | −32.0 (11) |
C24A—O4A—C17A—C18A | 85.9 (10) | C23B—O3B—C17B—C16B | 89.5 (11) |
C24A—O4A—C17A—C16A | −156.6 (9) | C23B—O3B—C17B—C18B | −153.6 (10) |
C23A—O3A—C17A—O4A | 25.1 (11) | C24B—O4B—C17B—O3B | 6.7 (11) |
C23A—O3A—C17A—C18A | −98.4 (11) | C24B—O4B—C17B—C16B | −114.5 (9) |
C23A—O3A—C17A—C16A | 144.9 (10) | C24B—O4B—C17B—C18B | 128.1 (9) |
C11A—C16A—C17A—O4A | −159.6 (8) | C11B—C16B—C17B—O3B | 81.9 (9) |
C11A—C16A—C17A—O3A | 84.3 (11) | C11B—C16B—C17B—O4B | −160.8 (8) |
C11A—C16A—C17A—C18A | −36.9 (11) | C11B—C16B—C17B—C18B | −39.1 (10) |
O4A—C17A—C18A—C12A | 158.9 (8) | C2B—C12B—C18B—C17B | 93.5 (10) |
O3A—C17A—C18A—C12A | −82.3 (10) | C13B—C12B—C18B—C17B | −133.6 (9) |
C16A—C17A—C18A—C12A | 37.9 (10) | C11B—C12B—C18B—C17B | −19.1 (11) |
C13A—C12A—C18A—C17A | −137.9 (9) | O3B—C17B—C18B—C12B | −84.3 (12) |
C2A—C12A—C18A—C17A | 89.9 (9) | O4B—C17B—C18B—C12B | 158.3 (8) |
C11A—C12A—C18A—C17A | −23.5 (9) | C16B—C17B—C18B—C12B | 36.6 (11) |
C14A—O1A—C19A—C21A | 163.7 (10) | C14B—O1B—C19B—C20B | 37.9 (11) |
C14A—O1A—C19A—C20A | 38.9 (10) | C14B—O1B—C19B—C21B | 161.1 (10) |
C14A—O2A—C20A—C19A | 25.4 (11) | C14B—O2B—C20B—C19B | 22.8 (12) |
C14A—O2A—C20A—C22A | 152.4 (10) | C14B—O2B—C20B—C22B | 146.6 (10) |
O1A—C19A—C20A—O2A | −38.8 (10) | O1B—C19B—C20B—O2B | −37.0 (11) |
C21A—C19A—C20A—O2A | −159.1 (9) | C21B—C19B—C20B—O2B | −155.7 (11) |
O1A—C19A—C20A—C22A | −161.1 (9) | O1B—C19B—C20B—C22B | −154.5 (10) |
C21A—C19A—C20A—C22A | 78.6 (13) | C21B—C19B—C20B—C22B | 86.8 (14) |
C17A—O3A—C23A—C25A | 120.6 (11) | C17B—O3B—C23B—C25B | 168.5 (11) |
C17A—O3A—C23A—C24A | −3.7 (12) | C17B—O3B—C23B—C24B | 42.9 (11) |
C17A—O4A—C24A—C26A | 158.6 (11) | C17B—O4B—C24B—C26B | 145.3 (11) |
C17A—O4A—C24A—C23A | 33.9 (12) | C17B—O4B—C24B—C23B | 19.3 (11) |
O3A—C23A—C24A—O4A | −18.0 (12) | O3B—C23B—C24B—O4B | −37.6 (10) |
C25A—C23A—C24A—O4A | −141.2 (12) | C25B—C23B—C24B—O4B | −156.8 (10) |
O3A—C23A—C24A—C26A | −137.3 (11) | O3B—C23B—C24B—C26B | −158.1 (11) |
C25A—C23A—C24A—C26A | 99.5 (14) | C25B—C23B—C24B—C26B | 82.7 (15) |
Experimental details
Crystal data | |
Chemical formula | C26H30O4 |
Mr | 406.50 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 200 |
a, b, c (Å) | 8.1172 (11), 22.523 (4), 12.5352 (13) |
β (°) | 105.362 (12) |
V (Å3) | 2209.9 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.40 × 0.32 |
Data collection | |
Diffractometer | Rigaku AFC-6S diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4276, 3990, 2388 |
Rint | 0.05 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.239, 1.07 |
No. of reflections | 3990 |
No. of parameters | 549 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0563P)2 + 10.0719P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.47, −0.52 |
Absolute structure | (Flack, 1983) |
Absolute structure parameter | 0 (4) |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1994), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), TEXSAN.
This project was designed to prepare chiral naphthalene systems with C2 symmetry for subsequent use as a chiral catalytic transfer agent [Cr(CO)3 from naphthalene to prochiral arene]. The reaction of acenaphthoquinone, (I), and 1,3-acetonedicarboxylate, (II), led to diketone (III), which upon reaction with two equivalents of (-)-(2R,3R)-butane-2,3-diol, (IV), gave the bis-ketal (V). To assess the potential regiochemistry of the two C2 acial asymmetry naphthalene rings toward Cr(CO)3 complexation, an X-ray structure of (V) was determined and is presented in this paper.
The asymmetric unit of (V) is composed of two independent molecules 1 and 2 wherein an acenaphthene moiety has been fused with two trans-2,3-dimethyl,1,4-dioxaspiro[4.4]nonane moieties (Figs. 1 and 2). The conformations of the dioxacyclopentane ring (G) in the two molecules are different from each other. The molecular dimensions in both molecules are as expected with mean bond distances: Csp3—Csp3 1.526 (17), Csp3—Csp2 1.515 (12), O—Csp3 1.434 (16) and C—Caromatic 1.393 (16) Å.
In both molecules, the acenaphthene moieties (rings A, B and C) are essentially planar with the maximum deviation of any atom from the mean-planes being 0.051 (9) and 0.054 (9) Å for molecules 1 and 2, respectively. The five-membered rings D, E, F and G in molecule 1 exhibit C14A–, C19A–, C17A– and O4A-envelope conformations, respectively, with these atoms 0.544 (17), 0.597 (17), 0.564 (16) and 0.504 (16) Å, respectively, out of the least-squares planes of the remaining ring atoms. The corresponging rings in molecule 2 adopt C14B–, C19B–, C17B– and C23B-envelope conformations, with these atoms 0.566 (17), 0.557 (16), 0.568 (15) and 0.618 (16) Å, respectively, out of the least-squares planes of the remaining ring atoms. The molecules are separated by normal van der Waals distances. In Fig. 3, a direct facial projection of a molecule 2 of (V) is shown, where the second ketal ring and H atoms have been omitted for clarity. This view illustrates that there is a small steric differentiation of the two aromatic rings.