Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016855/lh6433sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016855/lh6433Isup2.hkl |
CCDC reference: 277714
Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: SHELXL97.
C15H22O3 | F(000) = 1088 |
Mr = 250.32 | Dx = 1.089 Mg m−3 |
Monoclinic, P21/n | Melting point: 335 K |
Hall symbol: -P 2yn | Cu Kα radiation, λ = 1.54180 Å |
a = 14.861 (1) Å | Cell parameters from 1644 reflections |
b = 7.364 (1) Å | θ = 5.5–42.0° |
c = 27.948 (2) Å | µ = 0.60 mm−1 |
β = 93.42 (1)° | T = 296 K |
V = 3053.1 (5) Å3 | Rod, colourless |
Z = 8 | 0.70 × 0.18 × 0.10 mm |
Oxford Diffraction Xcalibur 3 CCD area-detector diffractometer | 4896 independent reflections |
Radiation source: fine-focus sealed tube | 2641 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 63.2°, θmin = 5.5° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1986) | h = −11→17 |
Tmin = 0.698, Tmax = 0.940 | k = −8→3 |
15432 measured reflections | l = −29→32 |
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)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.188 | w = 1/[σ2(Fo2) + (0.1355P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.86 | (Δ/σ)max < 0.001 |
4896 reflections | Δρmax = 0.64 e Å−3 |
336 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0008 (2) |
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 | ||
O1A | 0.84064 (11) | 0.2420 (2) | −0.10358 (7) | 0.0888 (6) | |
H1A | 0.8072 | 0.1798 | −0.1213 | 0.133* | |
O2A | 0.74933 (11) | 0.4583 (2) | −0.13176 (6) | 0.0793 (5) | |
C1A | 0.81658 (14) | 0.4119 (3) | −0.10742 (7) | 0.0573 (6) | |
C2A | 0.87609 (14) | 0.5449 (3) | −0.07967 (8) | 0.0601 (6) | |
C3A | 0.97659 (16) | 0.5082 (4) | −0.09063 (11) | 0.0854 (8) | |
H3A1 | 0.9933 | 0.3878 | −0.0804 | 0.128* | |
H3A2 | 1.0149 | 0.5950 | −0.0738 | 0.128* | |
H3A3 | 0.9833 | 0.5195 | −0.1245 | 0.128* | |
C4A | 0.85071 (16) | 0.7378 (3) | −0.09538 (9) | 0.0739 (7) | |
H4A1 | 0.8594 | 0.7514 | −0.1290 | 0.111* | |
H4A2 | 0.8882 | 0.8231 | −0.0775 | 0.111* | |
H4A3 | 0.7886 | 0.7600 | −0.0896 | 0.111* | |
C5A | 0.86619 (16) | 0.5159 (3) | −0.02594 (8) | 0.0693 (6) | |
H5A1 | 0.8908 | 0.3976 | −0.0172 | 0.083* | |
H5A2 | 0.9026 | 0.6062 | −0.0085 | 0.083* | |
C6A | 0.77289 (16) | 0.5263 (3) | −0.00967 (9) | 0.0726 (7) | |
H6A1 | 0.7374 | 0.4270 | −0.0236 | 0.087* | |
H6A2 | 0.7452 | 0.6393 | −0.0207 | 0.087* | |
C7A | 0.77268 (16) | 0.5164 (3) | 0.04428 (9) | 0.0688 (6) | |
H7A1 | 0.8013 | 0.4049 | 0.0557 | 0.083* | |
H7A2 | 0.8061 | 0.6180 | 0.0585 | 0.083* | |
O3A | 0.68164 (11) | 0.5216 (2) | 0.05771 (6) | 0.0810 (5) | |
C8A | 0.66839 (16) | 0.5220 (3) | 0.10553 (8) | 0.0615 (6) | |
C9A | 0.57719 (16) | 0.5318 (3) | 0.11610 (9) | 0.0701 (7) | |
C10A | 0.55913 (18) | 0.5329 (3) | 0.16381 (11) | 0.0768 (7) | |
H10A | 0.4994 | 0.5397 | 0.1718 | 0.092* | |
C11A | 0.6249 (2) | 0.5244 (3) | 0.19977 (10) | 0.0769 (7) | |
H11A | 0.6093 | 0.5254 | 0.2315 | 0.092* | |
C12A | 0.71425 (18) | 0.5144 (3) | 0.18979 (9) | 0.0719 (7) | |
C13A | 0.73511 (16) | 0.5135 (3) | 0.14187 (9) | 0.0673 (6) | |
H13A | 0.7951 | 0.5070 | 0.1343 | 0.081* | |
C14A | 0.5043 (2) | 0.5397 (5) | 0.07594 (12) | 0.1055 (10) | |
H141 | 0.4467 | 0.5547 | 0.0892 | 0.158* | |
H142 | 0.5046 | 0.4289 | 0.0578 | 0.158* | |
H143 | 0.5155 | 0.6404 | 0.0553 | 0.158* | |
C15A | 0.7886 (2) | 0.5059 (5) | 0.22902 (11) | 0.1155 (11) | |
H151 | 0.8247 | 0.6138 | 0.2281 | 0.173* | |
H152 | 0.8257 | 0.4014 | 0.2243 | 0.173* | |
H153 | 0.7627 | 0.4971 | 0.2596 | 0.173* | |
O1B | 0.64939 (11) | 0.2507 (2) | −0.19018 (7) | 0.0859 (6) | |
H1B | 0.6850 | 0.3123 | −0.1735 | 0.129* | |
O2B | 0.73129 (13) | 0.0316 (2) | −0.15769 (8) | 0.1056 (7) | |
C1B | 0.66943 (14) | 0.0801 (3) | −0.18476 (9) | 0.0628 (6) | |
C2B | 0.61071 (14) | −0.0497 (3) | −0.21414 (8) | 0.0626 (6) | |
C3B | 0.64388 (16) | −0.2446 (3) | −0.20470 (12) | 0.0908 (9) | |
H3B1 | 0.7059 | −0.2540 | −0.2122 | 0.136* | |
H3B2 | 0.6082 | −0.3272 | −0.2245 | 0.136* | |
H3B3 | 0.6382 | −0.2743 | −0.1716 | 0.136* | |
C4B | 0.6162 (2) | −0.0025 (4) | −0.26715 (10) | 0.0937 (9) | |
H4B1 | 0.5956 | 0.1197 | −0.2726 | 0.140* | |
H4B2 | 0.5789 | −0.0846 | −0.2862 | 0.140* | |
H4B3 | 0.6775 | −0.0129 | −0.2758 | 0.140* | |
C5B | 0.51205 (13) | −0.0268 (3) | −0.20068 (8) | 0.0618 (6) | |
H5B1 | 0.4908 | 0.0903 | −0.2125 | 0.074* | |
H5B2 | 0.4760 | −0.1190 | −0.2176 | 0.074* | |
C6B | 0.49389 (14) | −0.0388 (3) | −0.14779 (8) | 0.0642 (6) | |
H6B1 | 0.5171 | −0.1525 | −0.1346 | 0.077* | |
H6B2 | 0.5241 | 0.0600 | −0.1304 | 0.077* | |
C7B | 0.39459 (14) | −0.0278 (3) | −0.14232 (8) | 0.0638 (6) | |
H7B1 | 0.3710 | 0.0831 | −0.1570 | 0.077* | |
H7B2 | 0.3648 | −0.1298 | −0.1585 | 0.077* | |
O3B | 0.37669 (11) | −0.0302 (2) | −0.09299 (6) | 0.0774 (5) | |
C8B | 0.28840 (17) | −0.0219 (3) | −0.08185 (10) | 0.0689 (7) | |
C9B | 0.2729 (2) | −0.0284 (3) | −0.03294 (10) | 0.0793 (8) | |
C10B | 0.1842 (2) | −0.0211 (3) | −0.02031 (12) | 0.0887 (9) | |
H10B | 0.1721 | −0.0257 | 0.0119 | 0.106* | |
C11B | 0.1143 (2) | −0.0072 (3) | −0.05405 (15) | 0.0942 (10) | |
H11B | 0.0557 | −0.0030 | −0.0442 | 0.113* | |
C12B | 0.12809 (19) | 0.0009 (3) | −0.10278 (12) | 0.0851 (8) | |
C13B | 0.21793 (17) | −0.0074 (3) | −0.11535 (10) | 0.0752 (7) | |
H13B | 0.2300 | −0.0030 | −0.1476 | 0.090* | |
C14B | 0.3499 (3) | −0.0400 (5) | 0.00355 (12) | 0.1128 (11) | |
H144 | 0.3820 | −0.1514 | −0.0006 | 0.169* | |
H145 | 0.3275 | −0.0369 | 0.0351 | 0.169* | |
H146 | 0.3897 | 0.0609 | −0.0003 | 0.169* | |
C15B | 0.0525 (2) | 0.0186 (5) | −0.14121 (14) | 0.1129 (11) | |
H154 | −0.0035 | 0.0358 | −0.1265 | 0.169* | |
H155 | 0.0494 | −0.0899 | −0.1603 | 0.169* | |
H156 | 0.0639 | 0.1209 | −0.1613 | 0.169* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0834 (12) | 0.0681 (12) | 0.1101 (15) | 0.0050 (9) | −0.0348 (9) | −0.0104 (10) |
O2A | 0.0675 (10) | 0.0728 (11) | 0.0944 (13) | 0.0043 (8) | −0.0208 (9) | −0.0032 (9) |
C1A | 0.0540 (12) | 0.0654 (15) | 0.0522 (13) | −0.0012 (11) | 0.0019 (10) | 0.0007 (11) |
C2A | 0.0541 (12) | 0.0691 (15) | 0.0567 (13) | −0.0052 (10) | 0.0010 (10) | 0.0004 (11) |
C3A | 0.0589 (15) | 0.096 (2) | 0.099 (2) | −0.0073 (13) | −0.0094 (13) | −0.0088 (15) |
C4A | 0.0814 (16) | 0.0700 (16) | 0.0698 (15) | −0.0101 (12) | 0.0014 (12) | 0.0029 (12) |
C5A | 0.0757 (16) | 0.0755 (16) | 0.0564 (14) | −0.0070 (11) | 0.0007 (11) | −0.0026 (11) |
C6A | 0.0746 (16) | 0.0765 (16) | 0.0661 (16) | −0.0029 (12) | −0.0002 (12) | −0.0016 (12) |
C7A | 0.0629 (14) | 0.0745 (16) | 0.0696 (16) | −0.0044 (11) | 0.0086 (11) | −0.0006 (12) |
O3A | 0.0649 (10) | 0.1101 (14) | 0.0682 (11) | −0.0028 (8) | 0.0061 (8) | −0.0010 (9) |
C8A | 0.0743 (15) | 0.0597 (14) | 0.0510 (13) | −0.0031 (11) | 0.0091 (11) | −0.0002 (10) |
C9A | 0.0689 (15) | 0.0637 (15) | 0.0779 (17) | 0.0011 (11) | 0.0054 (12) | −0.0009 (12) |
C10A | 0.0736 (16) | 0.0677 (16) | 0.091 (2) | −0.0015 (12) | 0.0223 (15) | −0.0038 (14) |
C11A | 0.097 (2) | 0.0716 (16) | 0.0637 (16) | −0.0043 (13) | 0.0163 (14) | −0.0023 (13) |
C12A | 0.0803 (17) | 0.0712 (16) | 0.0641 (15) | −0.0033 (12) | 0.0029 (12) | 0.0016 (12) |
C13A | 0.0649 (14) | 0.0700 (16) | 0.0676 (16) | −0.0027 (11) | 0.0084 (12) | −0.0004 (12) |
C14A | 0.0784 (19) | 0.138 (3) | 0.099 (2) | 0.0054 (17) | −0.0034 (16) | 0.0049 (19) |
C15A | 0.123 (3) | 0.144 (3) | 0.075 (2) | −0.0032 (19) | −0.0236 (18) | 0.0037 (18) |
O1B | 0.0684 (11) | 0.0687 (12) | 0.1174 (15) | −0.0010 (8) | −0.0229 (9) | −0.0018 (10) |
O2B | 0.0964 (14) | 0.0723 (12) | 0.1408 (18) | 0.0064 (9) | −0.0538 (13) | −0.0042 (11) |
C1B | 0.0467 (12) | 0.0663 (16) | 0.0751 (16) | 0.0025 (11) | 0.0016 (11) | 0.0014 (12) |
C2B | 0.0485 (12) | 0.0737 (15) | 0.0657 (14) | −0.0040 (10) | 0.0052 (10) | −0.0089 (12) |
C3B | 0.0630 (14) | 0.0752 (18) | 0.135 (2) | 0.0040 (12) | 0.0105 (15) | −0.0287 (16) |
C4B | 0.0800 (18) | 0.129 (2) | 0.0724 (18) | −0.0244 (16) | 0.0121 (13) | −0.0160 (16) |
C5B | 0.0490 (12) | 0.0699 (14) | 0.0661 (14) | −0.0050 (10) | −0.0010 (10) | −0.0033 (11) |
C6B | 0.0580 (13) | 0.0682 (14) | 0.0665 (15) | −0.0033 (10) | 0.0047 (10) | −0.0010 (11) |
C7B | 0.0602 (13) | 0.0695 (15) | 0.0628 (15) | −0.0053 (10) | 0.0125 (11) | −0.0026 (11) |
O3B | 0.0731 (11) | 0.0918 (12) | 0.0691 (11) | −0.0030 (8) | 0.0188 (8) | −0.0016 (9) |
C8B | 0.0703 (16) | 0.0596 (14) | 0.0791 (17) | −0.0068 (11) | 0.0234 (13) | −0.0038 (12) |
C9B | 0.097 (2) | 0.0628 (15) | 0.0811 (19) | −0.0061 (13) | 0.0313 (16) | −0.0046 (13) |
C10B | 0.113 (2) | 0.0685 (17) | 0.089 (2) | −0.0133 (16) | 0.0425 (19) | −0.0096 (15) |
C11B | 0.095 (2) | 0.0664 (17) | 0.128 (3) | −0.0122 (15) | 0.059 (2) | −0.0137 (17) |
C12B | 0.0747 (18) | 0.0716 (17) | 0.112 (2) | −0.0114 (13) | 0.0336 (17) | −0.0096 (15) |
C13B | 0.0746 (16) | 0.0703 (16) | 0.0836 (18) | −0.0084 (12) | 0.0292 (14) | −0.0053 (13) |
C14B | 0.141 (3) | 0.121 (3) | 0.079 (2) | −0.001 (2) | 0.025 (2) | 0.0006 (18) |
C15B | 0.074 (2) | 0.126 (3) | 0.141 (3) | −0.0074 (16) | 0.0210 (19) | −0.009 (2) |
O1A—C1A | 1.304 (3) | O1B—C1B | 1.297 (3) |
O1A—H1A | 0.8200 | O1B—H1B | 0.8200 |
O2A—C1A | 1.224 (2) | O2B—C1B | 1.209 (3) |
C1A—C2A | 1.504 (3) | C1B—C2B | 1.505 (3) |
C2A—C4A | 1.527 (3) | C2B—C4B | 1.529 (4) |
C2A—C5A | 1.533 (3) | C2B—C3B | 1.535 (3) |
C2A—C3A | 1.566 (3) | C2B—C5B | 1.545 (3) |
C3A—H3A1 | 0.9600 | C3B—H3B1 | 0.9600 |
C3A—H3A2 | 0.9600 | C3B—H3B2 | 0.9600 |
C3A—H3A3 | 0.9600 | C3B—H3B3 | 0.9600 |
C4A—H4A1 | 0.9600 | C4B—H4B1 | 0.9600 |
C4A—H4A2 | 0.9600 | C4B—H4B2 | 0.9600 |
C4A—H4A3 | 0.9600 | C4B—H4B3 | 0.9600 |
C5A—C6A | 1.487 (3) | C5B—C6B | 1.521 (3) |
C5A—H5A1 | 0.9700 | C5B—H5B1 | 0.9700 |
C5A—H5A2 | 0.9700 | C5B—H5B2 | 0.9700 |
C6A—C7A | 1.510 (3) | C6B—C7B | 1.495 (3) |
C6A—H6A1 | 0.9700 | C6B—H6B1 | 0.9700 |
C6A—H6A2 | 0.9700 | C6B—H6B2 | 0.9700 |
C7A—O3A | 1.426 (3) | C7B—O3B | 1.420 (3) |
C7A—H7A1 | 0.9700 | C7B—H7B1 | 0.9700 |
C7A—H7A2 | 0.9700 | C7B—H7B2 | 0.9700 |
O3A—C8A | 1.362 (3) | O3B—C8B | 1.368 (3) |
C8A—C13A | 1.378 (3) | C8B—C13B | 1.367 (4) |
C8A—C9A | 1.406 (3) | C8B—C9B | 1.400 (4) |
C9A—C10A | 1.376 (3) | C9B—C10B | 1.385 (4) |
C9A—C14A | 1.513 (4) | C9B—C14B | 1.489 (4) |
C10A—C11A | 1.361 (4) | C10B—C11B | 1.364 (5) |
C10A—H10A | 0.9300 | C10B—H10B | 0.9300 |
C11A—C12A | 1.375 (3) | C11B—C12B | 1.390 (4) |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C13A | 1.393 (3) | C12B—C13B | 1.402 (3) |
C12A—C15A | 1.511 (4) | C12B—C15B | 1.512 (5) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—H141 | 0.9600 | C14B—H144 | 0.9600 |
C14A—H142 | 0.9600 | C14B—H145 | 0.9600 |
C14A—H143 | 0.9600 | C14B—H146 | 0.9600 |
C15A—H151 | 0.9600 | C15B—H154 | 0.9600 |
C15A—H152 | 0.9600 | C15B—H155 | 0.9600 |
C15A—H153 | 0.9600 | C15B—H156 | 0.9600 |
C1A—O1A—H1A | 109.5 | C1B—O1B—H1B | 109.5 |
O2A—C1A—O1A | 121.7 (2) | O2B—C1B—O1B | 121.3 (2) |
O2A—C1A—C2A | 122.7 (2) | O2B—C1B—C2B | 123.2 (2) |
O1A—C1A—C2A | 115.62 (19) | O1B—C1B—C2B | 115.4 (2) |
C1A—C2A—C4A | 109.27 (19) | C1B—C2B—C4B | 108.76 (19) |
C1A—C2A—C5A | 109.08 (17) | C1B—C2B—C3B | 109.3 (2) |
C4A—C2A—C5A | 112.00 (18) | C4B—C2B—C3B | 110.1 (2) |
C1A—C2A—C3A | 108.99 (18) | C1B—C2B—C5B | 109.01 (18) |
C4A—C2A—C3A | 109.02 (18) | C4B—C2B—C5B | 108.5 (2) |
C5A—C2A—C3A | 108.43 (19) | C3B—C2B—C5B | 111.10 (18) |
C2A—C3A—H3A1 | 109.5 | C2B—C3B—H3B1 | 109.5 |
C2A—C3A—H3A2 | 109.5 | C2B—C3B—H3B2 | 109.5 |
H3A1—C3A—H3A2 | 109.5 | H3B1—C3B—H3B2 | 109.5 |
C2A—C3A—H3A3 | 109.5 | C2B—C3B—H3B3 | 109.5 |
H3A1—C3A—H3A3 | 109.5 | H3B1—C3B—H3B3 | 109.5 |
H3A2—C3A—H3A3 | 109.5 | H3B2—C3B—H3B3 | 109.5 |
C2A—C4A—H4A1 | 109.5 | C2B—C4B—H4B1 | 109.5 |
C2A—C4A—H4A2 | 109.5 | C2B—C4B—H4B2 | 109.5 |
H4A1—C4A—H4A2 | 109.5 | H4B1—C4B—H4B2 | 109.5 |
C2A—C4A—H4A3 | 109.5 | C2B—C4B—H4B3 | 109.5 |
H4A1—C4A—H4A3 | 109.5 | H4B1—C4B—H4B3 | 109.5 |
H4A2—C4A—H4A3 | 109.5 | H4B2—C4B—H4B3 | 109.5 |
C6A—C5A—C2A | 116.0 (2) | C6B—C5B—C2B | 117.16 (18) |
C6A—C5A—H5A1 | 108.3 | C6B—C5B—H5B1 | 108.0 |
C2A—C5A—H5A1 | 108.3 | C2B—C5B—H5B1 | 108.0 |
C6A—C5A—H5A2 | 108.3 | C6B—C5B—H5B2 | 108.0 |
C2A—C5A—H5A2 | 108.3 | C2B—C5B—H5B2 | 108.0 |
H5A1—C5A—H5A2 | 107.4 | H5B1—C5B—H5B2 | 107.3 |
C5A—C6A—C7A | 111.1 (2) | C7B—C6B—C5B | 109.26 (18) |
C5A—C6A—H6A1 | 109.4 | C7B—C6B—H6B1 | 109.8 |
C7A—C6A—H6A1 | 109.4 | C5B—C6B—H6B1 | 109.8 |
C5A—C6A—H6A2 | 109.4 | C7B—C6B—H6B2 | 109.8 |
C7A—C6A—H6A2 | 109.4 | C5B—C6B—H6B2 | 109.8 |
H6A1—C6A—H6A2 | 108.0 | H6B1—C6B—H6B2 | 108.3 |
O3A—C7A—C6A | 108.7 (2) | O3B—C7B—C6B | 110.00 (19) |
O3A—C7A—H7A1 | 110.0 | O3B—C7B—H7B1 | 109.7 |
C6A—C7A—H7A1 | 110.0 | C6B—C7B—H7B1 | 109.7 |
O3A—C7A—H7A2 | 110.0 | O3B—C7B—H7B2 | 109.7 |
C6A—C7A—H7A2 | 110.0 | C6B—C7B—H7B2 | 109.7 |
H7A1—C7A—H7A2 | 108.3 | H7B1—C7B—H7B2 | 108.2 |
C8A—O3A—C7A | 116.96 (19) | C8B—O3B—C7B | 117.28 (19) |
O3A—C8A—C13A | 125.7 (2) | C13B—C8B—O3B | 123.6 (2) |
O3A—C8A—C9A | 113.8 (2) | C13B—C8B—C9B | 120.5 (2) |
C13A—C8A—C9A | 120.5 (2) | O3B—C8B—C9B | 115.9 (3) |
C10A—C9A—C8A | 116.8 (2) | C10B—C9B—C8B | 117.5 (3) |
C10A—C9A—C14A | 123.1 (2) | C10B—C9B—C14B | 122.1 (3) |
C8A—C9A—C14A | 120.1 (2) | C8B—C9B—C14B | 120.4 (2) |
C11A—C10A—C9A | 122.8 (2) | C11B—C10B—C9B | 121.5 (3) |
C11A—C10A—H10A | 118.6 | C11B—C10B—H10B | 119.2 |
C9A—C10A—H10A | 118.6 | C9B—C10B—H10B | 119.2 |
C10A—C11A—C12A | 120.8 (2) | C10B—C11B—C12B | 122.0 (3) |
C10A—C11A—H11A | 119.6 | C10B—C11B—H11B | 119.0 |
C12A—C11A—H11A | 119.6 | C12B—C11B—H11B | 119.0 |
C11A—C12A—C13A | 117.9 (2) | C11B—C12B—C13B | 116.2 (3) |
C11A—C12A—C15A | 121.9 (3) | C11B—C12B—C15B | 123.6 (3) |
C13A—C12A—C15A | 120.2 (3) | C13B—C12B—C15B | 120.2 (3) |
C8A—C13A—C12A | 121.1 (2) | C8B—C13B—C12B | 122.3 (3) |
C8A—C13A—H13A | 119.4 | C8B—C13B—H13B | 118.9 |
C12A—C13A—H13A | 119.4 | C12B—C13B—H13B | 118.9 |
C9A—C14A—H141 | 109.5 | C9B—C14B—H144 | 109.5 |
C9A—C14A—H142 | 109.5 | C9B—C14B—H145 | 109.5 |
H141—C14A—H142 | 109.5 | H144—C14B—H145 | 109.5 |
C9A—C14A—H143 | 109.5 | C9B—C14B—H146 | 109.5 |
H141—C14A—H143 | 109.5 | H144—C14B—H146 | 109.5 |
H142—C14A—H143 | 109.5 | H145—C14B—H146 | 109.5 |
C12A—C15A—H151 | 109.5 | C12B—C15B—H154 | 109.5 |
C12A—C15A—H152 | 109.5 | C12B—C15B—H155 | 109.5 |
H151—C15A—H152 | 109.5 | H154—C15B—H155 | 109.5 |
C12A—C15A—H153 | 109.5 | C12B—C15B—H156 | 109.5 |
H151—C15A—H153 | 109.5 | H154—C15B—H156 | 109.5 |
H152—C15A—H153 | 109.5 | H155—C15B—H156 | 109.5 |
O2A—C1A—C2A—C4A | −11.8 (3) | O2B—C1B—C2B—C4B | −121.6 (3) |
O1A—C1A—C2A—C4A | 168.87 (19) | O1B—C1B—C2B—C4B | 58.5 (3) |
O2A—C1A—C2A—C5A | 110.9 (2) | O2B—C1B—C2B—C3B | −1.3 (3) |
O1A—C1A—C2A—C5A | −68.4 (2) | O1B—C1B—C2B—C3B | 178.8 (2) |
O2A—C1A—C2A—C3A | −130.9 (2) | O2B—C1B—C2B—C5B | 120.3 (3) |
O1A—C1A—C2A—C3A | 49.8 (3) | O1B—C1B—C2B—C5B | −59.6 (3) |
C1A—C2A—C5A—C6A | −55.4 (3) | C1B—C2B—C5B—C6B | −52.5 (3) |
C4A—C2A—C5A—C6A | 65.7 (2) | C4B—C2B—C5B—C6B | −170.84 (19) |
C3A—C2A—C5A—C6A | −173.95 (19) | C3B—C2B—C5B—C6B | 68.0 (3) |
C2A—C5A—C6A—C7A | −173.74 (19) | C2B—C5B—C6B—C7B | −175.67 (18) |
C5A—C6A—C7A—O3A | −178.33 (18) | C5B—C6B—C7B—O3B | −177.28 (17) |
C6A—C7A—O3A—C8A | −177.22 (18) | C6B—C7B—O3B—C8B | −179.69 (18) |
C7A—O3A—C8A—C13A | −1.6 (3) | C7B—O3B—C8B—C13B | −1.6 (3) |
C7A—O3A—C8A—C9A | 178.49 (18) | C7B—O3B—C8B—C9B | 178.68 (19) |
O3A—C8A—C9A—C10A | −179.95 (19) | C13B—C8B—C9B—C10B | 0.5 (3) |
C13A—C8A—C9A—C10A | 0.2 (3) | O3B—C8B—C9B—C10B | −179.8 (2) |
O3A—C8A—C9A—C14A | 0.4 (3) | C13B—C8B—C9B—C14B | −178.6 (3) |
C13A—C8A—C9A—C14A | −179.5 (2) | O3B—C8B—C9B—C14B | 1.1 (3) |
C8A—C9A—C10A—C11A | −0.2 (3) | C8B—C9B—C10B—C11B | −0.3 (4) |
C14A—C9A—C10A—C11A | 179.5 (3) | C14B—C9B—C10B—C11B | 178.8 (3) |
C9A—C10A—C11A—C12A | 0.1 (4) | C9B—C10B—C11B—C12B | −0.2 (4) |
C10A—C11A—C12A—C13A | 0.1 (3) | C10B—C11B—C12B—C13B | 0.5 (4) |
C10A—C11A—C12A—C15A | 179.6 (3) | C10B—C11B—C12B—C15B | −179.2 (3) |
O3A—C8A—C13A—C12A | −179.9 (2) | O3B—C8B—C13B—C12B | −179.94 (19) |
C9A—C8A—C13A—C12A | 0.0 (3) | C9B—C8B—C13B—C12B | −0.2 (3) |
C11A—C12A—C13A—C8A | −0.1 (3) | C11B—C12B—C13B—C8B | −0.3 (3) |
C15A—C12A—C13A—C8A | −179.7 (3) | C15B—C12B—C13B—C8B | 179.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O2B | 0.82 | 1.83 | 2.652 (2) | 177 |
O1B—H1B···O2A | 0.82 | 1.82 | 2.631 (2) | 171 |