Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012669/hk2027sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012669/hk2027Isup2.hkl |
CCDC reference: 608354
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.036
- wR factor = 0.110
- Data-to-parameter ratio = 8.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 0.30 PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.78 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C31A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C71 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C31B PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT747_ALERT_1_C D...A Calc 3.066(4), Rep 3.06620 ...... Missing su C4 -O7 1.555 1.555 PLAT747_ALERT_1_C D...A Calc 2.929(4), Rep 2.92860 ...... Missing su C14 -O12 1.555 1.555 PLAT747_ALERT_1_C D...A Calc 2.895(4), Rep 2.89470 ...... Missing su C17 -O12 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 72.51 From the CIF: _reflns_number_total 2614 Count of symmetry unique reflns 2614 Completeness (_total/calc) 100.00% 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 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: PLATON (Spek, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
C26H38O6 | F(000) = 484 |
Mr = 446.56 | Dx = 1.207 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 10.8379 (11) Å | θ = 17.6–28.5° |
b = 8.3682 (11) Å | µ = 0.68 mm−1 |
c = 13.621 (8) Å | T = 298 K |
β = 95.92 (3)° | Prism, colourless |
V = 1228.7 (8) Å3 | 0.24 × 0.20 × 0.20 mm |
Z = 2 |
Enraf–Nonius MACH-3 diffractometer | 1905 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.053 |
Graphite monochromator | θmax = 72.5°, θmin = 3.3° |
profile data from ω/2θ scans | h = 0→13 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→10 |
Tmin = 0.774, Tmax = 0.873 | l = −16→16 |
5138 measured reflections | 3 standard reflections every 300 min |
2614 independent reflections | intensity decay: 9.6% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.1662P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.110 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.13 e Å−3 |
2614 reflections | Δρmin = −0.11 e Å−3 |
312 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0046 (7) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with no Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.3 (3) |
Experimental. Spectroscopic analysis: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 8.18 (1H, s), 8.10 (1H, s), 8.03 (1H, s), 5.67–5.56 (1H, m), 5.27 (1H, br t), 5.07 (1H, d, J = 2.5 Hz), 4.90 (1H, dd, J = 17.1 and 1.4 Hz), 4.83 (1H, dd, J = 10.1 and 1.8 Hz), 4.77–4.67 (1H, m), 0.96 (3H, s), 0.94 (3H, d, J = 64.5 Hz), 0.78 (3H, s); 13C NMR (75.25 MHz, CDCl3, δ, p.p.m.): 160.6 (two C atoms), 160.5, 144.2, 112.3, 75.1, 73.7, 70.7, 46.8, 44.9, 43.0, 40.8, 40.5, 37.7, 34.5, 34.4, 34.2, 31.3, 28.6, 27.3, 26.5, 25.6, 22.7, 22.4, 19.5, 12.3. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O3 | −0.0882 (3) | 0.4552 (4) | 0.0473 (2) | 0.0912 (9) | |
O7 | 0.15510 (18) | 0.1524 (3) | 0.31694 (15) | 0.0595 (6) | |
O12 | 0.45942 (18) | 0.1791 (3) | 0.11610 (14) | 0.0554 (5) | |
O31A | −0.1810 (6) | 0.6756 (8) | −0.0013 (6) | 0.149 (4) | 0.613 (8) |
O31B | −0.2425 (6) | 0.5447 (14) | 0.1049 (6) | 0.114 (4) | 0.387 (8) |
O71 | 0.0698 (4) | 0.0430 (6) | 0.4426 (3) | 0.1544 (18) | |
O121 | 0.5430 (3) | 0.2983 (4) | −0.00949 (19) | 0.0915 (9) | |
C1 | 0.2083 (3) | 0.6525 (4) | 0.1506 (2) | 0.0658 (9) | |
H1A | 0.1751 | 0.7568 | 0.1646 | 0.079* | |
H1B | 0.2854 | 0.6694 | 0.1216 | 0.079* | |
C2 | 0.1172 (3) | 0.5694 (5) | 0.0748 (2) | 0.0718 (10) | |
H2A | 0.1011 | 0.6363 | 0.0167 | 0.086* | |
H2B | 0.1521 | 0.4692 | 0.0550 | 0.086* | |
C3 | −0.0013 (3) | 0.5387 (4) | 0.1194 (2) | 0.0663 (9) | |
H3 | −0.0376 | 0.6409 | 0.1367 | 0.080* | |
C4 | 0.0213 (3) | 0.4364 (4) | 0.2110 (2) | 0.0600 (8) | |
H4A | 0.0543 | 0.3336 | 0.1938 | 0.072* | |
H4B | −0.0566 | 0.4182 | 0.2385 | 0.072* | |
C5 | 0.1126 (3) | 0.5179 (4) | 0.2879 (2) | 0.0546 (7) | |
H5 | 0.0738 | 0.6187 | 0.3047 | 0.066* | |
C6 | 0.1328 (3) | 0.4208 (4) | 0.3845 (2) | 0.0595 (8) | |
H6A | 0.1676 | 0.4910 | 0.4369 | 0.071* | |
H6B | 0.0528 | 0.3844 | 0.4017 | 0.071* | |
C7 | 0.2171 (3) | 0.2776 (4) | 0.3801 (2) | 0.0532 (7) | |
H7 | 0.2367 | 0.2350 | 0.4469 | 0.064* | |
C8 | 0.3375 (3) | 0.3173 (4) | 0.3368 (2) | 0.0462 (6) | |
H8 | 0.3851 | 0.3885 | 0.3836 | 0.055* | |
C9 | 0.3146 (3) | 0.4084 (4) | 0.2382 (2) | 0.0470 (6) | |
H9 | 0.2646 | 0.3382 | 0.1922 | 0.056* | |
C10 | 0.2375 (3) | 0.5628 (4) | 0.2487 (2) | 0.0519 (7) | |
C11 | 0.4368 (3) | 0.4395 (4) | 0.1935 (2) | 0.0535 (7) | |
H11A | 0.4176 | 0.4827 | 0.1276 | 0.064* | |
H11B | 0.4833 | 0.5200 | 0.2329 | 0.064* | |
C12 | 0.5192 (2) | 0.2917 (4) | 0.1871 (2) | 0.0485 (7) | |
H12 | 0.5987 | 0.3247 | 0.1652 | 0.058* | |
C13 | 0.5434 (2) | 0.2052 (3) | 0.28595 (19) | 0.0459 (6) | |
C14 | 0.4175 (2) | 0.1701 (4) | 0.32502 (19) | 0.0451 (6) | |
H14 | 0.3711 | 0.1030 | 0.2751 | 0.054* | |
C15 | 0.4499 (3) | 0.0638 (4) | 0.4141 (2) | 0.0547 (7) | |
H15A | 0.3816 | −0.0068 | 0.4247 | 0.066* | |
H15B | 0.4709 | 0.1270 | 0.4732 | 0.066* | |
C16 | 0.5637 (3) | −0.0323 (4) | 0.3868 (2) | 0.0551 (7) | |
H16A | 0.6333 | −0.0180 | 0.4368 | 0.066* | |
H16B | 0.5440 | −0.1453 | 0.3818 | 0.066* | |
C17 | 0.5958 (2) | 0.0323 (4) | 0.2866 (2) | 0.0496 (7) | |
H17 | 0.5454 | −0.0274 | 0.2351 | 0.060* | |
C18 | 0.6273 (3) | 0.3131 (4) | 0.3556 (2) | 0.0588 (8) | |
H18A | 0.7041 | 0.3313 | 0.3281 | 0.088* | |
H18B | 0.6436 | 0.2620 | 0.4187 | 0.088* | |
H18C | 0.5865 | 0.4134 | 0.3636 | 0.088* | |
C19 | 0.3085 (3) | 0.6827 (4) | 0.3197 (3) | 0.0696 (9) | |
H19A | 0.3377 | 0.6293 | 0.3801 | 0.104* | |
H19B | 0.2542 | 0.7685 | 0.3336 | 0.104* | |
H19C | 0.3779 | 0.7248 | 0.2896 | 0.104* | |
C20 | 0.7330 (3) | 0.0013 (4) | 0.2718 (2) | 0.0594 (8) | |
H20 | 0.7851 | 0.0549 | 0.3249 | 0.071* | |
C21 | 0.7693 (4) | 0.0617 (6) | 0.1733 (3) | 0.0883 (13) | |
H21A | 0.8522 | 0.0275 | 0.1651 | 0.132* | |
H21B | 0.7657 | 0.1763 | 0.1720 | 0.132* | |
H21C | 0.7130 | 0.0195 | 0.1206 | 0.132* | |
C22 | 0.7566 (3) | −0.1761 (5) | 0.2797 (3) | 0.0731 (10) | |
H22 | 0.7138 | −0.2404 | 0.2320 | 0.088* | |
C23 | 0.8307 (4) | −0.2474 (6) | 0.3462 (3) | 0.0881 (12) | |
H23A | 0.8756 | −0.1881 | 0.3954 | 0.106* | |
H23B | 0.8390 | −0.3579 | 0.3448 | 0.106* | |
C31A | −0.1746 (10) | 0.5396 (14) | −0.0041 (8) | 0.092 (3) | 0.613 (8) |
H31A | −0.2342 | 0.4850 | −0.0453 | 0.111* | 0.613 (8) |
C31B | −0.1953 (12) | 0.477 (2) | 0.0427 (13) | 0.080 (4) | 0.387 (8) |
H31B | −0.2450 | 0.4396 | −0.0122 | 0.096* | 0.387 (8) |
C71 | 0.0867 (4) | 0.0472 (5) | 0.3579 (3) | 0.0829 (11) | |
H71 | 0.0480 | −0.0309 | 0.3170 | 0.100* | |
C121 | 0.4798 (3) | 0.1984 (5) | 0.0229 (2) | 0.0660 (9) | |
H121 | 0.4408 | 0.1266 | −0.0222 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.092 (2) | 0.0736 (18) | 0.1001 (19) | 0.0190 (16) | −0.0270 (16) | −0.0263 (16) |
O7 | 0.0540 (11) | 0.0581 (13) | 0.0685 (13) | −0.0075 (10) | 0.0167 (10) | 0.0003 (11) |
O12 | 0.0587 (11) | 0.0600 (13) | 0.0488 (10) | −0.0012 (11) | 0.0122 (9) | −0.0012 (10) |
O31A | 0.134 (5) | 0.077 (4) | 0.213 (8) | 0.000 (4) | −0.088 (5) | 0.015 (5) |
O31B | 0.057 (4) | 0.164 (10) | 0.116 (7) | 0.009 (5) | −0.007 (4) | −0.063 (7) |
O71 | 0.195 (4) | 0.162 (4) | 0.117 (3) | −0.095 (4) | 0.070 (3) | 0.009 (3) |
O121 | 0.118 (2) | 0.102 (2) | 0.0607 (14) | −0.010 (2) | 0.0373 (14) | 0.0042 (16) |
C1 | 0.068 (2) | 0.0506 (18) | 0.081 (2) | 0.0085 (17) | 0.0206 (17) | 0.0097 (18) |
C2 | 0.092 (2) | 0.066 (2) | 0.0578 (18) | 0.018 (2) | 0.0079 (17) | 0.0069 (17) |
C3 | 0.0678 (19) | 0.059 (2) | 0.070 (2) | 0.0127 (18) | −0.0048 (16) | −0.0132 (17) |
C4 | 0.0536 (16) | 0.059 (2) | 0.0680 (18) | 0.0016 (16) | 0.0075 (14) | −0.0034 (17) |
C5 | 0.0555 (15) | 0.0504 (17) | 0.0596 (16) | 0.0079 (14) | 0.0137 (13) | −0.0031 (15) |
C6 | 0.0580 (17) | 0.068 (2) | 0.0548 (16) | 0.0047 (17) | 0.0170 (13) | −0.0083 (17) |
C7 | 0.0495 (14) | 0.0614 (19) | 0.0507 (15) | 0.0025 (15) | 0.0146 (12) | 0.0003 (15) |
C8 | 0.0464 (14) | 0.0489 (16) | 0.0453 (14) | −0.0018 (13) | 0.0142 (11) | −0.0007 (13) |
C9 | 0.0477 (14) | 0.0458 (14) | 0.0488 (14) | −0.0003 (12) | 0.0106 (11) | −0.0007 (13) |
C10 | 0.0543 (15) | 0.0433 (15) | 0.0593 (16) | 0.0047 (14) | 0.0121 (13) | −0.0013 (14) |
C11 | 0.0559 (15) | 0.0489 (17) | 0.0584 (17) | 0.0003 (14) | 0.0198 (13) | 0.0063 (14) |
C12 | 0.0465 (14) | 0.0511 (17) | 0.0499 (15) | −0.0064 (13) | 0.0142 (12) | −0.0043 (14) |
C13 | 0.0449 (13) | 0.0480 (16) | 0.0460 (14) | −0.0039 (13) | 0.0112 (11) | −0.0039 (13) |
C14 | 0.0467 (13) | 0.0478 (15) | 0.0420 (13) | −0.0009 (13) | 0.0097 (11) | 0.0018 (13) |
C15 | 0.0541 (15) | 0.0590 (18) | 0.0524 (15) | 0.0007 (15) | 0.0125 (12) | 0.0060 (15) |
C16 | 0.0520 (15) | 0.0548 (18) | 0.0588 (17) | 0.0011 (14) | 0.0074 (13) | 0.0061 (15) |
C17 | 0.0459 (14) | 0.0537 (17) | 0.0495 (15) | 0.0002 (14) | 0.0068 (11) | −0.0021 (13) |
C18 | 0.0541 (16) | 0.0616 (19) | 0.0613 (17) | −0.0080 (15) | 0.0085 (14) | −0.0124 (16) |
C19 | 0.0665 (19) | 0.0507 (19) | 0.092 (2) | −0.0001 (17) | 0.0109 (17) | −0.0145 (19) |
C20 | 0.0501 (16) | 0.064 (2) | 0.0651 (18) | 0.0098 (15) | 0.0119 (13) | 0.0001 (16) |
C21 | 0.072 (2) | 0.114 (4) | 0.084 (2) | 0.025 (3) | 0.0336 (19) | 0.020 (3) |
C22 | 0.064 (2) | 0.070 (2) | 0.085 (2) | 0.0177 (19) | 0.0108 (19) | −0.008 (2) |
C23 | 0.078 (2) | 0.076 (3) | 0.115 (3) | 0.017 (2) | 0.034 (2) | 0.008 (3) |
C31A | 0.083 (6) | 0.089 (7) | 0.099 (7) | 0.006 (5) | −0.023 (5) | −0.001 (5) |
C31B | 0.062 (6) | 0.089 (10) | 0.086 (9) | 0.005 (7) | −0.005 (6) | −0.038 (8) |
C71 | 0.076 (2) | 0.074 (3) | 0.104 (3) | −0.015 (2) | 0.031 (2) | 0.010 (2) |
C121 | 0.073 (2) | 0.075 (2) | 0.0507 (18) | 0.007 (2) | 0.0121 (15) | −0.0050 (18) |
O3—C31B | 1.170 (13) | C11—H11B | 0.9700 |
O3—C31A | 1.316 (10) | C12—C13 | 1.527 (4) |
O3—C3 | 1.466 (4) | C12—H12 | 0.9800 |
O7—C71 | 1.313 (4) | C13—C18 | 1.538 (4) |
O7—C7 | 1.473 (4) | C13—C14 | 1.543 (3) |
O71—C71 | 1.187 (5) | C13—C17 | 1.554 (4) |
O12—C121 | 1.320 (4) | C14—C15 | 1.517 (4) |
O12—C12 | 1.454 (3) | C14—H14 | 0.9800 |
O121—C121 | 1.193 (4) | C15—C16 | 1.549 (4) |
C1—C2 | 1.521 (5) | C15—H15A | 0.9700 |
C1—C10 | 1.536 (4) | C15—H15B | 0.9700 |
C1—H1A | 0.9700 | C16—C17 | 1.541 (4) |
C1—H1B | 0.9700 | C16—H16A | 0.9700 |
C2—C3 | 1.498 (5) | C16—H16B | 0.9700 |
C2—H2A | 0.9700 | C17—C20 | 1.543 (4) |
C2—H2B | 0.9700 | C17—H17 | 0.9800 |
C3—C4 | 1.513 (5) | C18—H18A | 0.9600 |
C3—H3 | 0.9800 | C18—H18B | 0.9600 |
C4—C5 | 1.525 (4) | C18—H18C | 0.9600 |
C4—H4A | 0.9700 | C19—H19A | 0.9600 |
C4—H4B | 0.9700 | C19—H19B | 0.9600 |
C5—C6 | 1.542 (4) | C19—H19C | 0.9600 |
C5—C10 | 1.552 (4) | C20—C22 | 1.508 (5) |
C5—H5 | 0.9800 | C20—C21 | 1.524 (5) |
C6—C7 | 1.512 (4) | C20—H20 | 0.9800 |
C6—H6A | 0.9700 | C21—H21A | 0.9600 |
C6—H6B | 0.9700 | C21—H21B | 0.9600 |
C7—C8 | 1.524 (4) | C21—H21C | 0.9600 |
C7—H7 | 0.9800 | C22—C23 | 1.292 (5) |
C8—C14 | 1.524 (4) | C22—H22 | 0.9300 |
C8—C9 | 1.541 (4) | C23—H23A | 0.9300 |
C8—H8 | 0.9800 | C23—H23B | 0.9300 |
C9—C11 | 1.536 (4) | C71—H71 | 0.9300 |
C9—C10 | 1.554 (4) | C121—H121 | 0.9300 |
C9—H9 | 0.9800 | C31A—O31A | 1.141 (11) |
C10—C19 | 1.543 (5) | C31A—H31A | 0.9300 |
C11—C12 | 1.533 (4) | C31B—O31B | 1.179 (14) |
C11—H11A | 0.9700 | C31B—H31B | 0.9300 |
C31B—O3—C3 | 121.8 (7) | C13—C12—H12 | 109.0 |
C31A—O3—C3 | 118.3 (5) | C11—C12—H12 | 109.0 |
C71—O7—C7 | 118.2 (3) | C12—C13—C18 | 107.6 (2) |
C121—O12—C12 | 116.9 (3) | C12—C13—C14 | 108.4 (2) |
C2—C1—C10 | 115.3 (3) | C18—C13—C14 | 112.7 (2) |
C2—C1—H1A | 108.4 | C12—C13—C17 | 118.4 (2) |
C10—C1—H1A | 108.4 | C18—C13—C17 | 110.5 (2) |
C2—C1—H1B | 108.4 | C14—C13—C17 | 99.0 (2) |
C10—C1—H1B | 108.4 | C15—C14—C8 | 118.5 (2) |
H1A—C1—H1B | 107.5 | C15—C14—C13 | 104.3 (2) |
C3—C2—C1 | 109.1 (3) | C8—C14—C13 | 114.5 (2) |
C3—C2—H2A | 109.9 | C15—C14—H14 | 106.2 |
C1—C2—H2A | 109.9 | C8—C14—H14 | 106.2 |
C3—C2—H2B | 109.9 | C13—C14—H14 | 106.2 |
C1—C2—H2B | 109.9 | C14—C15—C16 | 103.7 (2) |
H2A—C2—H2B | 108.3 | C14—C15—H15A | 111.0 |
O3—C3—C2 | 109.2 (3) | C16—C15—H15A | 111.0 |
O3—C3—C4 | 108.7 (3) | C14—C15—H15B | 111.0 |
C2—C3—C4 | 111.0 (3) | C16—C15—H15B | 111.0 |
O3—C3—H3 | 109.3 | H15A—C15—H15B | 109.0 |
C2—C3—H3 | 109.3 | C17—C16—C15 | 106.8 (2) |
C4—C3—H3 | 109.3 | C17—C16—H16A | 110.4 |
C3—C4—C5 | 110.6 (3) | C15—C16—H16A | 110.4 |
C3—C4—H4A | 109.5 | C17—C16—H16B | 110.4 |
C5—C4—H4A | 109.5 | C15—C16—H16B | 110.4 |
C3—C4—H4B | 109.5 | H16A—C16—H16B | 108.6 |
C5—C4—H4B | 109.5 | C16—C17—C20 | 111.4 (2) |
H4A—C4—H4B | 108.1 | C16—C17—C13 | 102.5 (2) |
C4—C5—C6 | 112.1 (3) | C20—C17—C13 | 120.8 (2) |
C4—C5—C10 | 113.5 (2) | C16—C17—H17 | 107.1 |
C6—C5—C10 | 111.7 (2) | C20—C17—H17 | 107.1 |
C4—C5—H5 | 106.3 | C13—C17—H17 | 107.1 |
C6—C5—H5 | 106.3 | C13—C18—H18A | 109.5 |
C10—C5—H5 | 106.3 | C13—C18—H18B | 109.5 |
C7—C6—C5 | 114.7 (2) | H18A—C18—H18B | 109.5 |
C7—C6—H6A | 108.6 | C13—C18—H18C | 109.5 |
C5—C6—H6A | 108.6 | H18A—C18—H18C | 109.5 |
C7—C6—H6B | 108.6 | H18B—C18—H18C | 109.5 |
C5—C6—H6B | 108.6 | C10—C19—H19A | 109.5 |
H6A—C6—H6B | 107.6 | C10—C19—H19B | 109.5 |
O7—C7—C6 | 110.2 (2) | H19A—C19—H19B | 109.5 |
O7—C7—C8 | 106.6 (2) | C10—C19—H19C | 109.5 |
C6—C7—C8 | 112.8 (3) | H19A—C19—H19C | 109.5 |
O7—C7—H7 | 109.0 | H19B—C19—H19C | 109.5 |
C6—C7—H7 | 109.0 | C22—C20—C21 | 109.4 (3) |
C8—C7—H7 | 109.0 | C22—C20—C17 | 108.4 (3) |
C14—C8—C7 | 112.5 (2) | C21—C20—C17 | 113.5 (3) |
C14—C8—C9 | 110.5 (2) | C22—C20—H20 | 108.5 |
C7—C8—C9 | 112.2 (2) | C21—C20—H20 | 108.5 |
C14—C8—H8 | 107.1 | C17—C20—H20 | 108.5 |
C7—C8—H8 | 107.1 | C20—C21—H21A | 109.5 |
C9—C8—H8 | 107.1 | C20—C21—H21B | 109.5 |
C11—C9—C8 | 111.1 (2) | H21A—C21—H21B | 109.5 |
C11—C9—C10 | 112.9 (2) | C20—C21—H21C | 109.5 |
C8—C9—C10 | 111.8 (2) | H21A—C21—H21C | 109.5 |
C11—C9—H9 | 106.9 | H21B—C21—H21C | 109.5 |
C8—C9—H9 | 106.9 | C23—C22—C20 | 126.4 (4) |
C10—C9—H9 | 106.9 | C23—C22—H22 | 116.8 |
C1—C10—C19 | 105.8 (3) | C20—C22—H22 | 116.8 |
C1—C10—C5 | 108.0 (2) | C22—C23—H23A | 120.0 |
C19—C10—C5 | 109.8 (2) | C22—C23—H23B | 120.0 |
C1—C10—C9 | 113.0 (2) | H23A—C23—H23B | 120.0 |
C19—C10—C9 | 111.1 (2) | O71—C71—O7 | 125.7 (4) |
C5—C10—C9 | 109.0 (2) | O71—C71—H71 | 117.1 |
C12—C11—C9 | 114.6 (2) | O7—C71—H71 | 117.1 |
C12—C11—H11A | 108.6 | O121—C121—O12 | 126.9 (4) |
C9—C11—H11A | 108.6 | O121—C121—H121 | 116.5 |
C12—C11—H11B | 108.6 | O12—C121—H121 | 116.5 |
C9—C11—H11B | 108.6 | O31A—C31A—O3 | 124.0 (9) |
H11A—C11—H11B | 107.6 | O31A—C31A—H31A | 118.0 |
O12—C12—C13 | 107.7 (2) | O3—C31A—H31A | 118.0 |
O12—C12—C11 | 109.8 (2) | O3—C31B—O31B | 122.6 (12) |
C13—C12—C11 | 112.4 (2) | O3—C31B—H31B | 118.7 |
O12—C12—H12 | 109.0 | O31B—C31B—H31B | 118.7 |
C10—C1—C2—C3 | 56.8 (4) | C9—C11—C12—O12 | 67.3 (3) |
C31B—O3—C3—C2 | −145.9 (13) | C9—C11—C12—C13 | −52.5 (3) |
C31A—O3—C3—C2 | −98.9 (8) | O12—C12—C13—C18 | 169.8 (2) |
C31B—O3—C3—C4 | 92.8 (13) | C11—C12—C13—C18 | −69.2 (3) |
C31A—O3—C3—C4 | 139.8 (7) | O12—C12—C13—C14 | −68.0 (3) |
C1—C2—C3—O3 | −178.6 (3) | C11—C12—C13—C14 | 53.0 (3) |
C1—C2—C3—C4 | −58.8 (4) | O12—C12—C13—C17 | 43.6 (3) |
O3—C3—C4—C5 | 179.4 (3) | C11—C12—C13—C17 | 164.6 (2) |
C2—C3—C4—C5 | 59.2 (4) | C7—C8—C14—C15 | −53.4 (3) |
C3—C4—C5—C6 | 177.1 (2) | C9—C8—C14—C15 | −179.7 (2) |
C3—C4—C5—C10 | −55.3 (3) | C7—C8—C14—C13 | −177.2 (2) |
C4—C5—C6—C7 | 77.2 (3) | C9—C8—C14—C13 | 56.5 (3) |
C10—C5—C6—C7 | −51.4 (4) | C12—C13—C14—C15 | 171.8 (2) |
C71—O7—C7—C6 | −88.7 (3) | C18—C13—C14—C15 | −69.1 (3) |
C71—O7—C7—C8 | 148.5 (3) | C17—C13—C14—C15 | 47.7 (3) |
C5—C6—C7—O7 | −70.5 (3) | C12—C13—C14—C8 | −57.0 (3) |
C5—C6—C7—C8 | 48.5 (4) | C18—C13—C14—C8 | 62.1 (3) |
O7—C7—C8—C14 | −54.4 (3) | C17—C13—C14—C8 | 178.9 (2) |
C6—C7—C8—C14 | −175.5 (2) | C8—C14—C15—C16 | −161.0 (2) |
O7—C7—C8—C9 | 71.0 (3) | C13—C14—C15—C16 | −32.2 (3) |
C6—C7—C8—C9 | −50.1 (3) | C14—C15—C16—C17 | 3.8 (3) |
C14—C8—C9—C11 | −50.6 (3) | C15—C16—C17—C20 | 156.1 (3) |
C7—C8—C9—C11 | −177.1 (3) | C15—C16—C17—C13 | 25.5 (3) |
C14—C8—C9—C10 | −177.8 (2) | C12—C13—C17—C16 | −160.7 (2) |
C7—C8—C9—C10 | 55.7 (3) | C18—C13—C17—C16 | 74.6 (3) |
C2—C1—C10—C19 | −168.8 (3) | C14—C13—C17—C16 | −43.9 (3) |
C2—C1—C10—C5 | −51.3 (4) | C12—C13—C17—C20 | 74.8 (3) |
C2—C1—C10—C9 | 69.4 (3) | C18—C13—C17—C20 | −50.0 (3) |
C4—C5—C10—C1 | 49.8 (4) | C14—C13—C17—C20 | −168.5 (3) |
C6—C5—C10—C1 | 177.6 (3) | C16—C17—C20—C22 | 57.7 (4) |
C4—C5—C10—C19 | 164.7 (3) | C13—C17—C20—C22 | 178.0 (3) |
C6—C5—C10—C19 | −67.5 (3) | C16—C17—C20—C21 | 179.5 (3) |
C4—C5—C10—C9 | −73.4 (3) | C13—C17—C20—C21 | −60.2 (4) |
C6—C5—C10—C9 | 54.5 (3) | C21—C20—C22—C23 | 119.6 (5) |
C11—C9—C10—C1 | 56.3 (3) | C17—C20—C22—C23 | −116.1 (4) |
C8—C9—C10—C1 | −177.6 (2) | C7—O7—C71—O71 | −0.1 (6) |
C11—C9—C10—C19 | −62.5 (3) | C12—O12—C121—O121 | 0.5 (5) |
C8—C9—C10—C19 | 63.7 (3) | C31B—O3—C31A—O31A | 113 (2) |
C11—C9—C10—C5 | 176.4 (2) | C3—O3—C31A—O31A | 5.8 (18) |
C8—C9—C10—C5 | −57.4 (3) | C31A—O3—C31B—O31B | −111 (3) |
C8—C9—C11—C12 | 50.2 (3) | C3—O3—C31B—O31B | −13 (3) |
C10—C9—C11—C12 | 176.8 (3) | C17—C20—C22—C23 | −116.1 (4) |
C121—O12—C12—C13 | −150.2 (3) | C21—C20—C22—C23 | 119.6 (5) |
C121—O12—C12—C11 | 87.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O31Ai | 0.97 | 2.59 | 3.5331 | 164 |
C4—H4A···O7 | 0.97 | 2.43 | 3.0662 | 122 |
C14—H14···O12 | 0.98 | 2.54 | 2.9286 | 104 |
C17—H17···O12 | 0.98 | 2.48 | 2.8947 | 105 |
C22—H22···O31Bii | 0.93 | 2.57 | 3.3366 | 140 |
C31A—H31B···O121iii | 1.13 | 2.59 | 3.6611 | 158 |
C121—H121···O31Bi | 0.93 | 2.42 | 3.2211 | 144 |
Symmetry codes: (i) −x, y−1/2, −z; (ii) x+1, y−1, z; (iii) x−1, y, z. |
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