Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012834/ci2312sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012834/ci2312Isup2.hkl |
CCDC reference: 643639
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C20H32O2 | F(000) = 672 |
Mr = 304.46 | Dx = 1.201 Mg m−3 |
Monoclinic, P21 | Melting point = 528–530 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6496 (4) Å | Cell parameters from 4787 reflections |
b = 7.8597 (3) Å | θ = 1.0–29.0° |
c = 20.3159 (7) Å | µ = 0.08 mm−1 |
β = 97.907 (2)° | T = 100 K |
V = 1684.33 (11) Å3 | Needle, colourless |
Z = 4 | 0.56 × 0.24 × 0.12 mm |
Bruker SMART APEX II CCD area-detector diffractometer | 5031 independent reflections |
Radiation source: fine-focus sealed tube | 4395 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
Detector resolution: 8.33 pixels mm-1 | θmax = 29.6°, θmin = 1.0° |
ω scans | h = −11→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −10→10 |
Tmin = 0.960, Tmax = 0.991 | l = −28→24 |
19242 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1985P] where P = (Fo2 + 2Fc2)/3 |
5031 reflections | (Δ/σ)max = 0.001 |
417 parameters | Δρmax = 0.31 e Å−3 |
1 restraint | Δρmin = −0.19 e Å−3 |
Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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 | 0.64178 (15) | 0.1975 (2) | 0.27673 (7) | 0.0252 (3) | |
O2A | 0.56408 (14) | 0.2230 (2) | 0.71930 (7) | 0.0243 (3) | |
C1A | 0.71855 (18) | 0.0051 (3) | 0.49586 (9) | 0.0188 (4) | |
C2A | 0.7384 (2) | −0.1775 (3) | 0.47064 (10) | 0.0245 (4) | |
H2AB | 0.8256 | −0.2111 | 0.4846 | 0.029* | |
H2AC | 0.6843 | −0.2550 | 0.4911 | 0.029* | |
C3A | 0.7092 (2) | −0.1946 (3) | 0.39523 (10) | 0.0282 (5) | |
H3AA | 0.7267 | −0.3102 | 0.3825 | 0.034* | |
H3AB | 0.6198 | −0.1724 | 0.3814 | 0.034* | |
C4A | 0.7876 (2) | −0.0717 (3) | 0.35991 (10) | 0.0272 (5) | |
H4AA | 0.7618 | −0.0820 | 0.3124 | 0.033* | |
H4AB | 0.8759 | −0.1053 | 0.3690 | 0.033* | |
C5A | 0.77639 (19) | 0.1157 (3) | 0.37974 (9) | 0.0215 (4) | |
C6A | 0.79664 (18) | 0.1295 (3) | 0.45731 (9) | 0.0185 (4) | |
H6AA | 0.8847 | 0.0936 | 0.4702 | 0.022* | |
C7A | 0.7930 (2) | 0.3104 (3) | 0.48440 (9) | 0.0214 (4) | |
H7AA | 0.7058 | 0.3479 | 0.4825 | 0.026* | |
H7AB | 0.8361 | 0.3872 | 0.4576 | 0.026* | |
C8A | 0.85853 (19) | 0.3139 (3) | 0.55675 (9) | 0.0228 (4) | |
H8AA | 0.9468 | 0.2825 | 0.5577 | 0.027* | |
H8AB | 0.8559 | 0.4289 | 0.5738 | 0.027* | |
C9A | 0.79720 (18) | 0.1939 (3) | 0.60212 (9) | 0.0182 (4) | |
C10A | 0.77826 (18) | 0.0143 (3) | 0.57104 (9) | 0.0189 (4) | |
H10A | 0.8644 | −0.0299 | 0.5717 | 0.023* | |
C11A | 0.7173 (2) | −0.1050 (3) | 0.61833 (10) | 0.0216 (4) | |
H11A | 0.6794 | −0.2005 | 0.5926 | 0.026* | |
H11B | 0.7841 | −0.1498 | 0.6510 | 0.026* | |
C12A | 0.6157 (2) | −0.0244 (3) | 0.65542 (10) | 0.0224 (4) | |
H12A | 0.5366 | −0.0160 | 0.6255 | 0.027* | |
H12B | 0.6014 | −0.0973 | 0.6922 | 0.027* | |
C13A | 0.65476 (18) | 0.1520 (3) | 0.68184 (9) | 0.0199 (4) | |
C14A | 0.67345 (18) | 0.2646 (3) | 0.62293 (9) | 0.0193 (4) | |
H14A | 0.6827 | 0.3832 | 0.6360 | 0.023* | |
H14B | 0.6033 | 0.2535 | 0.5873 | 0.023* | |
C15A | 0.87961 (18) | 0.1803 (3) | 0.67138 (9) | 0.0225 (4) | |
H15A | 0.9406 | 0.0885 | 0.6717 | 0.027* | |
H15B | 0.9251 | 0.2857 | 0.6824 | 0.027* | |
C16A | 0.78785 (19) | 0.1451 (3) | 0.72028 (10) | 0.0205 (4) | |
C17A | 0.57506 (18) | 0.0422 (3) | 0.48618 (10) | 0.0208 (4) | |
H17A | 0.5378 | 0.0025 | 0.4432 | 0.031* | |
H17B | 0.5615 | 0.1625 | 0.4893 | 0.031* | |
H17C | 0.5365 | −0.0154 | 0.5200 | 0.031* | |
C18A | 0.8833 (2) | 0.2151 (4) | 0.35268 (10) | 0.0286 (5) | |
H18A | 0.8828 | 0.1887 | 0.3065 | 0.043* | |
H18B | 0.9636 | 0.1835 | 0.3771 | 0.043* | |
H18C | 0.8700 | 0.3350 | 0.3576 | 0.043* | |
C19A | 0.65014 (19) | 0.1916 (3) | 0.34806 (9) | 0.0243 (5) | |
H19A | 0.5810 | 0.1235 | 0.3603 | 0.029* | |
H19B | 0.6416 | 0.3058 | 0.3650 | 0.029* | |
C20A | 0.8130 (2) | 0.1195 (3) | 0.78496 (10) | 0.0235 (4) | |
H20A | 0.8964 | 0.1220 | 0.8058 | 0.028* | |
H20B | 0.7474 | 0.0989 | 0.8097 | 0.028* | |
O1B | 0.39586 (16) | 0.0197 (3) | 0.77040 (8) | 0.0302 (4) | |
O2B | 0.42173 (16) | 0.0349 (2) | 1.22463 (8) | 0.0264 (3) | |
C1B | 0.27791 (18) | 0.1997 (3) | 0.97099 (9) | 0.0176 (4) | |
C2B | 0.2448 (2) | 0.3767 (3) | 0.93981 (11) | 0.0235 (4) | |
H2BB | 0.1553 | 0.3982 | 0.9403 | 0.028* | |
H2BC | 0.2918 | 0.4627 | 0.9672 | 0.028* | |
C3B | 0.2741 (2) | 0.3949 (3) | 0.86863 (11) | 0.0277 (5) | |
H3BA | 0.2461 | 0.5059 | 0.8516 | 0.033* | |
H3BB | 0.3650 | 0.3879 | 0.8686 | 0.033* | |
C4B | 0.2091 (2) | 0.2576 (3) | 0.82328 (10) | 0.0264 (5) | |
H4BA | 0.2336 | 0.2710 | 0.7793 | 0.032* | |
H4BB | 0.1181 | 0.2737 | 0.8194 | 0.032* | |
C5B | 0.24126 (19) | 0.0758 (3) | 0.84777 (10) | 0.0205 (4) | |
C6B | 0.21579 (18) | 0.0623 (3) | 0.92142 (9) | 0.0178 (4) | |
H6BA | 0.1248 | 0.0851 | 0.9188 | 0.021* | |
C7B | 0.23072 (19) | −0.1156 (3) | 0.95164 (10) | 0.0195 (4) | |
H7BA | 0.3198 | −0.1397 | 0.9653 | 0.023* | |
H7BB | 0.1976 | −0.1995 | 0.9188 | 0.023* | |
C8B | 0.15885 (19) | −0.1265 (3) | 1.01184 (10) | 0.0200 (4) | |
H8BA | 0.0692 | −0.1093 | 0.9972 | 0.024* | |
H8BB | 0.1694 | −0.2397 | 1.0308 | 0.024* | |
C9B | 0.20387 (18) | 0.0039 (3) | 1.06539 (9) | 0.0174 (4) | |
C10B | 0.21090 (18) | 0.1844 (3) | 1.03498 (9) | 0.0175 (4) | |
H10B | 0.1224 | 0.2149 | 1.0200 | 0.021* | |
C11B | 0.2555 (2) | 0.3148 (3) | 1.09064 (10) | 0.0229 (4) | |
H11C | 0.2888 | 0.4138 | 1.0704 | 0.027* | |
H11D | 0.1821 | 0.3514 | 1.1104 | 0.027* | |
C12B | 0.3564 (2) | 0.2517 (3) | 1.14638 (10) | 0.0234 (4) | |
H12C | 0.4385 | 0.2529 | 1.1308 | 0.028* | |
H12D | 0.3602 | 0.3288 | 1.1839 | 0.028* | |
C13B | 0.3288 (2) | 0.0720 (3) | 1.16926 (10) | 0.0205 (4) | |
C14B | 0.32863 (18) | −0.0466 (3) | 1.10936 (9) | 0.0181 (4) | |
H14C | 0.3275 | −0.1652 | 1.1225 | 0.022* | |
H14D | 0.4016 | −0.0264 | 1.0867 | 0.022* | |
C15B | 0.11238 (19) | 0.0094 (3) | 1.11891 (9) | 0.0230 (4) | |
H15C | 0.0449 | 0.0909 | 1.1066 | 0.028* | |
H15D | 0.0750 | −0.1017 | 1.1237 | 0.028* | |
C16B | 0.1920 (2) | 0.0620 (3) | 1.18283 (10) | 0.0228 (4) | |
C17B | 0.42266 (18) | 0.1852 (3) | 0.98662 (10) | 0.0219 (4) | |
H17D | 0.4609 | 0.2301 | 0.9502 | 0.033* | |
H17E | 0.4460 | 0.0679 | 0.9933 | 0.033* | |
H17F | 0.4517 | 0.2486 | 1.0262 | 0.033* | |
C18B | 0.1541 (2) | −0.0497 (3) | 0.80514 (10) | 0.0262 (5) | |
H18D | 0.1470 | −0.0164 | 0.7593 | 0.039* | |
H18E | 0.0717 | −0.0488 | 0.8192 | 0.039* | |
H18F | 0.1893 | −0.1621 | 0.8103 | 0.039* | |
C19B | 0.3788 (2) | 0.0310 (3) | 0.83892 (10) | 0.0263 (5) | |
H19C | 0.4353 | 0.1173 | 0.8605 | 0.032* | |
H19D | 0.4014 | −0.0769 | 0.8605 | 0.032* | |
C20B | 0.1534 (3) | 0.0917 (3) | 1.24102 (11) | 0.0318 (5) | |
H20C | 0.0680 | 0.0806 | 1.2456 | 0.038* | |
H20D | 0.2116 | 0.1237 | 1.2773 | 0.038* | |
H1AA | 0.581 (3) | 0.139 (5) | 0.2623 (17) | 0.057 (11)* | |
H2AA | 0.510 (3) | 0.154 (5) | 0.7321 (17) | 0.062 (11)* | |
H1BA | 0.376 (3) | −0.083 (5) | 0.7555 (15) | 0.044 (9)* | |
H2BA | 0.408 (3) | −0.059 (5) | 1.2357 (14) | 0.037 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0237 (7) | 0.0356 (10) | 0.0154 (6) | −0.0012 (7) | −0.0002 (6) | 0.0002 (7) |
O2A | 0.0218 (7) | 0.0285 (9) | 0.0243 (7) | −0.0006 (7) | 0.0094 (6) | −0.0061 (7) |
C1A | 0.0190 (9) | 0.0209 (11) | 0.0165 (8) | 0.0003 (8) | 0.0019 (7) | −0.0032 (8) |
C2A | 0.0281 (11) | 0.0237 (11) | 0.0219 (10) | 0.0012 (9) | 0.0039 (8) | −0.0033 (9) |
C3A | 0.0325 (11) | 0.0276 (12) | 0.0239 (10) | 0.0038 (10) | 0.0025 (9) | −0.0106 (9) |
C4A | 0.0279 (11) | 0.0368 (14) | 0.0172 (9) | 0.0088 (10) | 0.0036 (8) | −0.0045 (9) |
C5A | 0.0179 (9) | 0.0331 (12) | 0.0132 (8) | 0.0040 (9) | 0.0011 (7) | 0.0002 (8) |
C6A | 0.0154 (9) | 0.0257 (11) | 0.0139 (8) | 0.0011 (8) | 0.0003 (7) | 0.0010 (8) |
C7A | 0.0222 (10) | 0.0262 (11) | 0.0159 (9) | −0.0029 (9) | 0.0028 (7) | 0.0011 (8) |
C8A | 0.0225 (10) | 0.0282 (12) | 0.0182 (9) | −0.0074 (9) | 0.0041 (7) | −0.0010 (9) |
C9A | 0.0169 (8) | 0.0240 (11) | 0.0136 (8) | −0.0017 (8) | 0.0015 (7) | 0.0007 (8) |
C10A | 0.0185 (9) | 0.0228 (11) | 0.0158 (8) | 0.0012 (8) | 0.0034 (7) | 0.0006 (8) |
C11A | 0.0268 (10) | 0.0194 (10) | 0.0191 (9) | 0.0007 (9) | 0.0049 (8) | −0.0001 (8) |
C12A | 0.0240 (10) | 0.0253 (11) | 0.0186 (9) | −0.0041 (9) | 0.0058 (7) | −0.0013 (8) |
C13A | 0.0179 (9) | 0.0260 (11) | 0.0167 (8) | −0.0006 (8) | 0.0050 (7) | −0.0021 (8) |
C14A | 0.0208 (9) | 0.0202 (10) | 0.0171 (8) | −0.0009 (8) | 0.0028 (7) | −0.0013 (8) |
C15A | 0.0191 (9) | 0.0314 (12) | 0.0165 (8) | −0.0013 (9) | 0.0005 (7) | −0.0007 (8) |
C16A | 0.0224 (9) | 0.0206 (10) | 0.0182 (9) | −0.0005 (8) | 0.0023 (7) | −0.0021 (8) |
C17A | 0.0180 (9) | 0.0262 (11) | 0.0183 (8) | −0.0027 (8) | 0.0031 (7) | −0.0042 (8) |
C18A | 0.0223 (10) | 0.0464 (15) | 0.0177 (9) | 0.0025 (10) | 0.0045 (8) | 0.0032 (10) |
C19A | 0.0209 (9) | 0.0368 (13) | 0.0148 (8) | 0.0044 (9) | 0.0010 (7) | −0.0009 (9) |
C20A | 0.0250 (10) | 0.0267 (12) | 0.0189 (9) | 0.0026 (9) | 0.0033 (8) | 0.0010 (8) |
O1B | 0.0367 (9) | 0.0330 (10) | 0.0243 (7) | −0.0005 (8) | 0.0164 (7) | −0.0006 (7) |
O2B | 0.0304 (8) | 0.0242 (9) | 0.0216 (7) | −0.0046 (7) | −0.0070 (6) | 0.0028 (7) |
C1B | 0.0167 (9) | 0.0191 (10) | 0.0171 (8) | −0.0003 (8) | 0.0024 (7) | 0.0014 (8) |
C2B | 0.0267 (10) | 0.0199 (11) | 0.0234 (10) | 0.0029 (9) | 0.0012 (8) | 0.0035 (8) |
C3B | 0.0342 (12) | 0.0245 (12) | 0.0240 (10) | 0.0019 (10) | 0.0031 (9) | 0.0088 (9) |
C4B | 0.0298 (11) | 0.0313 (12) | 0.0187 (9) | 0.0070 (10) | 0.0051 (8) | 0.0064 (9) |
C5B | 0.0207 (9) | 0.0253 (11) | 0.0157 (8) | 0.0045 (8) | 0.0036 (7) | 0.0024 (8) |
C6B | 0.0154 (9) | 0.0217 (11) | 0.0170 (8) | 0.0024 (8) | 0.0044 (7) | 0.0001 (8) |
C7B | 0.0212 (9) | 0.0202 (10) | 0.0175 (9) | −0.0006 (8) | 0.0042 (7) | −0.0027 (8) |
C8B | 0.0227 (9) | 0.0198 (11) | 0.0180 (9) | −0.0057 (8) | 0.0044 (7) | −0.0019 (8) |
C9B | 0.0174 (9) | 0.0190 (10) | 0.0159 (8) | −0.0019 (8) | 0.0031 (7) | −0.0021 (8) |
C10B | 0.0180 (9) | 0.0175 (10) | 0.0171 (8) | 0.0023 (8) | 0.0030 (7) | −0.0010 (7) |
C11B | 0.0291 (11) | 0.0191 (10) | 0.0195 (9) | −0.0005 (9) | 0.0000 (8) | −0.0023 (8) |
C12B | 0.0283 (10) | 0.0200 (11) | 0.0203 (9) | −0.0055 (9) | −0.0021 (8) | −0.0010 (8) |
C13B | 0.0233 (10) | 0.0208 (10) | 0.0163 (8) | −0.0016 (8) | −0.0011 (7) | −0.0013 (8) |
C14B | 0.0181 (9) | 0.0175 (10) | 0.0182 (9) | −0.0010 (8) | 0.0007 (7) | 0.0006 (8) |
C15B | 0.0199 (9) | 0.0297 (12) | 0.0204 (9) | −0.0016 (9) | 0.0066 (7) | −0.0011 (9) |
C16B | 0.0286 (10) | 0.0203 (11) | 0.0199 (9) | 0.0006 (9) | 0.0043 (8) | 0.0003 (8) |
C17B | 0.0181 (9) | 0.0234 (11) | 0.0242 (9) | −0.0026 (8) | 0.0026 (7) | 0.0045 (9) |
C18B | 0.0268 (11) | 0.0324 (13) | 0.0188 (9) | 0.0049 (9) | 0.0011 (8) | −0.0020 (9) |
C19B | 0.0248 (10) | 0.0360 (13) | 0.0195 (9) | 0.0064 (10) | 0.0083 (8) | 0.0025 (9) |
C20B | 0.0433 (13) | 0.0313 (13) | 0.0223 (10) | 0.0022 (11) | 0.0095 (9) | −0.0041 (9) |
O1A—C19A | 1.440 (2) | O1B—C19B | 1.431 (2) |
O1A—H1AA | 0.81 (4) | O1B—H1BA | 0.88 (4) |
O2A—C13A | 1.423 (2) | O2B—C13B | 1.422 (3) |
O2A—H2AA | 0.85 (4) | O2B—H2BA | 0.79 (3) |
C1A—C17A | 1.541 (3) | C1B—C17B | 1.535 (3) |
C1A—C2A | 1.548 (3) | C1B—C2B | 1.548 (3) |
C1A—C6A | 1.562 (3) | C1B—C6B | 1.561 (3) |
C1A—C10A | 1.573 (3) | C1B—C10B | 1.571 (3) |
C2A—C3A | 1.527 (3) | C2B—C3B | 1.527 (3) |
C2A—H2AB | 0.97 | C2B—H2BB | 0.97 |
C2A—H2AC | 0.97 | C2B—H2BC | 0.97 |
C3A—C4A | 1.519 (3) | C3B—C4B | 1.522 (4) |
C3A—H3AA | 0.97 | C3B—H3BA | 0.97 |
C3A—H3AB | 0.97 | C3B—H3BB | 0.97 |
C4A—C5A | 1.536 (4) | C4B—C5B | 1.536 (3) |
C4A—H4AA | 0.97 | C4B—H4BA | 0.97 |
C4A—H4AB | 0.97 | C4B—H4BB | 0.97 |
C5A—C19A | 1.530 (3) | C5B—C18B | 1.537 (3) |
C5A—C18A | 1.543 (3) | C5B—C19B | 1.541 (3) |
C5A—C6A | 1.565 (3) | C5B—C6B | 1.561 (3) |
C6A—C7A | 1.527 (3) | C6B—C7B | 1.526 (3) |
C6A—H6AA | 0.98 | C6B—H6BA | 0.98 |
C7A—C8A | 1.538 (3) | C7B—C8B | 1.532 (3) |
C7A—H7AA | 0.97 | C7B—H7BA | 0.97 |
C7A—H7AB | 0.97 | C7B—H7BB | 0.97 |
C8A—C9A | 1.527 (3) | C8B—C9B | 1.523 (3) |
C8A—H8AA | 0.97 | C8B—H8BA | 0.97 |
C8A—H8AB | 0.97 | C8B—H8BB | 0.97 |
C9A—C14A | 1.542 (3) | C9B—C14B | 1.547 (3) |
C9A—C10A | 1.548 (3) | C9B—C10B | 1.553 (3) |
C9A—C15A | 1.556 (3) | C9B—C15B | 1.557 (3) |
C10A—C11A | 1.548 (3) | C10B—C11B | 1.551 (3) |
C10A—H10A | 0.98 | C10B—H10B | 0.98 |
C11A—C12A | 1.538 (3) | C11B—C12B | 1.532 (3) |
C11A—H11A | 0.97 | C11B—H11C | 0.97 |
C11A—H11B | 0.97 | C11B—H11D | 0.97 |
C12A—C13A | 1.524 (3) | C12B—C13B | 1.528 (3) |
C12A—H12A | 0.97 | C12B—H12C | 0.97 |
C12A—H12B | 0.97 | C12B—H12D | 0.97 |
C13A—C16A | 1.522 (3) | C13B—C16B | 1.522 (3) |
C13A—C14A | 1.523 (3) | C13B—C14B | 1.533 (3) |
C14A—H14A | 0.97 | C14B—H14C | 0.97 |
C14A—H14B | 0.97 | C14B—H14D | 0.97 |
C15A—C16A | 1.512 (3) | C15B—C16B | 1.508 (3) |
C15A—H15A | 0.97 | C15B—H15C | 0.97 |
C15A—H15B | 0.97 | C15B—H15D | 0.97 |
C16A—C20A | 1.320 (3) | C16B—C20B | 1.325 (3) |
C17A—H17A | 0.96 | C17B—H17D | 0.96 |
C17A—H17B | 0.96 | C17B—H17E | 0.96 |
C17A—H17C | 0.96 | C17B—H17F | 0.96 |
C18A—H18A | 0.96 | C18B—H18D | 0.96 |
C18A—H18B | 0.96 | C18B—H18E | 0.96 |
C18A—H18C | 0.96 | C18B—H18F | 0.96 |
C19A—H19A | 0.97 | C19B—H19C | 0.97 |
C19A—H19B | 0.97 | C19B—H19D | 0.97 |
C20A—H20A | 0.93 | C20B—H20C | 0.93 |
C20A—H20B | 0.93 | C20B—H20D | 0.93 |
C19A—O1A—H1AA | 106 (2) | C19B—O1B—H1BA | 110 (2) |
C13A—O2A—H2AA | 116 (2) | C13B—O2B—H2BA | 107 (2) |
C17A—C1A—C2A | 108.10 (17) | C17B—C1B—C2B | 108.47 (17) |
C17A—C1A—C6A | 113.87 (17) | C17B—C1B—C6B | 114.00 (17) |
C2A—C1A—C6A | 107.94 (15) | C2B—C1B—C6B | 107.78 (16) |
C17A—C1A—C10A | 112.12 (15) | C17B—C1B—C10B | 112.37 (16) |
C2A—C1A—C10A | 107.96 (17) | C2B—C1B—C10B | 107.68 (16) |
C6A—C1A—C10A | 106.63 (15) | C6B—C1B—C10B | 106.28 (15) |
C3A—C2A—C1A | 113.28 (19) | C3B—C2B—C1B | 114.02 (18) |
C3A—C2A—H2AB | 108.9 | C3B—C2B—H2BB | 108.7 |
C1A—C2A—H2AB | 108.9 | C1B—C2B—H2BB | 108.7 |
C3A—C2A—H2AC | 108.9 | C3B—C2B—H2BC | 108.7 |
C1A—C2A—H2AC | 108.9 | C1B—C2B—H2BC | 108.7 |
H2AB—C2A—H2AC | 107.7 | H2BB—C2B—H2BC | 107.6 |
C4A—C3A—C2A | 111.65 (19) | C4B—C3B—C2B | 111.82 (19) |
C4A—C3A—H3AA | 109.3 | C4B—C3B—H3BA | 109.3 |
C2A—C3A—H3AA | 109.3 | C2B—C3B—H3BA | 109.3 |
C4A—C3A—H3AB | 109.3 | C4B—C3B—H3BB | 109.3 |
C2A—C3A—H3AB | 109.3 | C2B—C3B—H3BB | 109.3 |
H3AA—C3A—H3AB | 108.0 | H3BA—C3B—H3BB | 107.9 |
C3A—C4A—C5A | 114.71 (17) | C3B—C4B—C5B | 113.62 (17) |
C3A—C4A—H4AA | 108.6 | C3B—C4B—H4BA | 108.8 |
C5A—C4A—H4AA | 108.6 | C5B—C4B—H4BA | 108.8 |
C3A—C4A—H4AB | 108.6 | C3B—C4B—H4BB | 108.8 |
C5A—C4A—H4AB | 108.6 | C5B—C4B—H4BB | 108.8 |
H4AA—C4A—H4AB | 107.6 | H4BA—C4B—H4BB | 107.7 |
C19A—C5A—C4A | 111.05 (19) | C4B—C5B—C18B | 108.90 (17) |
C19A—C5A—C18A | 107.55 (18) | C4B—C5B—C19B | 110.36 (19) |
C4A—C5A—C18A | 107.74 (18) | C18B—C5B—C19B | 107.29 (18) |
C19A—C5A—C6A | 112.83 (16) | C4B—C5B—C6B | 108.28 (17) |
C4A—C5A—C6A | 109.01 (18) | C18B—C5B—C6B | 108.99 (17) |
C18A—C5A—C6A | 108.51 (17) | C19B—C5B—C6B | 112.94 (16) |
C7A—C6A—C1A | 111.13 (15) | C7B—C6B—C5B | 115.21 (17) |
C7A—C6A—C5A | 114.88 (17) | C7B—C6B—C1B | 111.29 (16) |
C1A—C6A—C5A | 116.91 (17) | C5B—C6B—C1B | 117.21 (17) |
C7A—C6A—H6AA | 104.0 | C7B—C6B—H6BA | 103.7 |
C1A—C6A—H6AA | 104.0 | C5B—C6B—H6BA | 103.7 |
C5A—C6A—H6AA | 104.0 | C1B—C6B—H6BA | 103.7 |
C6A—C7A—C8A | 109.27 (18) | C6B—C7B—C8B | 109.67 (16) |
C6A—C7A—H7AA | 109.8 | C6B—C7B—H7BA | 109.7 |
C8A—C7A—H7AA | 109.8 | C8B—C7B—H7BA | 109.7 |
C6A—C7A—H7AB | 109.8 | C6B—C7B—H7BB | 109.7 |
C8A—C7A—H7AB | 109.8 | C8B—C7B—H7BB | 109.7 |
H7AA—C7A—H7AB | 108.3 | H7BA—C7B—H7BB | 108.2 |
C9A—C8A—C7A | 113.00 (17) | C9B—C8B—C7B | 112.94 (16) |
C9A—C8A—H8AA | 109.0 | C9B—C8B—H8BA | 109.0 |
C7A—C8A—H8AA | 109.0 | C7B—C8B—H8BA | 109.0 |
C9A—C8A—H8AB | 109.0 | C9B—C8B—H8BB | 109.0 |
C7A—C8A—H8AB | 109.0 | C7B—C8B—H8BB | 109.0 |
H8AA—C8A—H8AB | 107.8 | H8BA—C8B—H8BB | 107.8 |
C8A—C9A—C14A | 113.29 (18) | C8B—C9B—C14B | 113.59 (17) |
C8A—C9A—C10A | 111.07 (15) | C8B—C9B—C10B | 110.99 (15) |
C14A—C9A—C10A | 111.86 (16) | C14B—C9B—C10B | 112.32 (16) |
C8A—C9A—C15A | 110.69 (16) | C8B—C9B—C15B | 110.58 (16) |
C14A—C9A—C15A | 100.00 (15) | C14B—C9B—C15B | 100.02 (15) |
C10A—C9A—C15A | 109.38 (17) | C10B—C9B—C15B | 108.76 (16) |
C11A—C10A—C9A | 109.97 (15) | C11B—C10B—C9B | 109.87 (16) |
C11A—C10A—C1A | 115.27 (17) | C11B—C10B—C1B | 115.08 (17) |
C9A—C10A—C1A | 116.76 (17) | C9B—C10B—C1B | 116.84 (16) |
C11A—C10A—H10A | 104.4 | C11B—C10B—H10B | 104.5 |
C9A—C10A—H10A | 104.4 | C9B—C10B—H10B | 104.5 |
C1A—C10A—H10A | 104.4 | C1B—C10B—H10B | 104.5 |
C12A—C11A—C10A | 115.99 (18) | C12B—C11B—C10B | 116.00 (19) |
C12A—C11A—H11A | 108.3 | C12B—C11B—H11C | 108.3 |
C10A—C11A—H11A | 108.3 | C10B—C11B—H11C | 108.3 |
C12A—C11A—H11B | 108.3 | C12B—C11B—H11D | 108.3 |
C10A—C11A—H11B | 108.3 | C10B—C11B—H11D | 108.3 |
H11A—C11A—H11B | 107.4 | H11C—C11B—H11D | 107.4 |
C13A—C12A—C11A | 111.75 (17) | C13B—C12B—C11B | 112.33 (18) |
C13A—C12A—H12A | 109.3 | C13B—C12B—H12C | 109.1 |
C11A—C12A—H12A | 109.3 | C11B—C12B—H12C | 109.1 |
C13A—C12A—H12B | 109.3 | C13B—C12B—H12D | 109.1 |
C11A—C12A—H12B | 109.3 | C11B—C12B—H12D | 109.1 |
H12A—C12A—H12B | 107.9 | H12C—C12B—H12D | 107.9 |
O2A—C13A—C16A | 113.08 (16) | O2B—C13B—C16B | 115.17 (17) |
O2A—C13A—C14A | 111.33 (18) | O2B—C13B—C12B | 106.76 (17) |
C16A—C13A—C14A | 102.17 (16) | C16B—C13B—C12B | 109.34 (18) |
O2A—C13A—C12A | 111.87 (17) | O2B—C13B—C14B | 115.36 (18) |
C16A—C13A—C12A | 109.76 (18) | C16B—C13B—C14B | 102.45 (16) |
C14A—C13A—C12A | 108.12 (16) | C12B—C13B—C14B | 107.46 (16) |
C13A—C14A—C9A | 102.40 (16) | C13B—C14B—C9B | 102.09 (16) |
C13A—C14A—H14A | 111.3 | C13B—C14B—H14C | 111.4 |
C9A—C14A—H14A | 111.3 | C9B—C14B—H14C | 111.4 |
C13A—C14A—H14B | 111.3 | C13B—C14B—H14D | 111.4 |
C9A—C14A—H14B | 111.3 | C9B—C14B—H14D | 111.4 |
H14A—C14A—H14B | 109.2 | H14C—C14B—H14D | 109.2 |
C16A—C15A—C9A | 105.76 (16) | C16B—C15B—C9B | 106.11 (16) |
C16A—C15A—H15A | 110.6 | C16B—C15B—H15C | 110.5 |
C9A—C15A—H15A | 110.6 | C9B—C15B—H15C | 110.5 |
C16A—C15A—H15B | 110.6 | C16B—C15B—H15D | 110.5 |
C9A—C15A—H15B | 110.6 | C9B—C15B—H15D | 110.5 |
H15A—C15A—H15B | 108.7 | H15C—C15B—H15D | 108.7 |
C20A—C16A—C15A | 128.39 (19) | C20B—C16B—C15B | 127.6 (2) |
C20A—C16A—C13A | 124.30 (18) | C20B—C16B—C13B | 125.1 (2) |
C15A—C16A—C13A | 107.26 (16) | C15B—C16B—C13B | 107.28 (16) |
C1A—C17A—H17A | 109.5 | C1B—C17B—H17D | 109.5 |
C1A—C17A—H17B | 109.5 | C1B—C17B—H17E | 109.5 |
H17A—C17A—H17B | 109.5 | H17D—C17B—H17E | 109.5 |
C1A—C17A—H17C | 109.5 | C1B—C17B—H17F | 109.5 |
H17A—C17A—H17C | 109.5 | H17D—C17B—H17F | 109.5 |
H17B—C17A—H17C | 109.5 | H17E—C17B—H17F | 109.5 |
C5A—C18A—H18A | 109.5 | C5B—C18B—H18D | 109.5 |
C5A—C18A—H18B | 109.5 | C5B—C18B—H18E | 109.5 |
H18A—C18A—H18B | 109.5 | H18D—C18B—H18E | 109.5 |
C5A—C18A—H18C | 109.5 | C5B—C18B—H18F | 109.5 |
H18A—C18A—H18C | 109.5 | H18D—C18B—H18F | 109.5 |
H18B—C18A—H18C | 109.5 | H18E—C18B—H18F | 109.5 |
O1A—C19A—C5A | 111.40 (16) | O1B—C19B—C5B | 112.21 (17) |
O1A—C19A—H19A | 109.3 | O1B—C19B—H19C | 109.2 |
C5A—C19A—H19A | 109.3 | C5B—C19B—H19C | 109.2 |
O1A—C19A—H19B | 109.3 | O1B—C19B—H19D | 109.2 |
C5A—C19A—H19B | 109.3 | C5B—C19B—H19D | 109.2 |
H19A—C19A—H19B | 108.0 | H19C—C19B—H19D | 107.9 |
C16A—C20A—H20A | 120.0 | C16B—C20B—H20C | 120.0 |
C16A—C20A—H20B | 120.0 | C16B—C20B—H20D | 120.0 |
H20A—C20A—H20B | 120.0 | H20C—C20B—H20D | 120.0 |
C17A—C1A—C2A—C3A | 70.2 (2) | C17B—C1B—C2B—C3B | 72.8 (2) |
C6A—C1A—C2A—C3A | −53.4 (2) | C6B—C1B—C2B—C3B | −51.1 (2) |
C10A—C1A—C2A—C3A | −168.31 (17) | C10B—C1B—C2B—C3B | −165.33 (18) |
C1A—C2A—C3A—C4A | 56.6 (3) | C1B—C2B—C3B—C4B | 55.4 (2) |
C2A—C3A—C4A—C5A | −54.6 (3) | C2B—C3B—C4B—C5B | −55.8 (2) |
C3A—C4A—C5A—C19A | −75.5 (2) | C3B—C4B—C5B—C18B | 170.59 (18) |
C3A—C4A—C5A—C18A | 166.94 (18) | C3B—C4B—C5B—C19B | −71.9 (2) |
C3A—C4A—C5A—C6A | 49.4 (2) | C3B—C4B—C5B—C6B | 52.2 (2) |
C17A—C1A—C6A—C7A | 65.8 (2) | C4B—C5B—C6B—C7B | 174.33 (17) |
C2A—C1A—C6A—C7A | −174.15 (17) | C18B—C5B—C6B—C7B | 56.0 (2) |
C10A—C1A—C6A—C7A | −58.4 (2) | C19B—C5B—C6B—C7B | −63.1 (2) |
C17A—C1A—C6A—C5A | −68.8 (2) | C4B—C5B—C6B—C1B | −51.8 (2) |
C2A—C1A—C6A—C5A | 51.3 (2) | C18B—C5B—C6B—C1B | −170.11 (17) |
C10A—C1A—C6A—C5A | 167.06 (17) | C19B—C5B—C6B—C1B | 70.8 (2) |
C19A—C5A—C6A—C7A | −58.3 (2) | C17B—C1B—C6B—C7B | 66.1 (2) |
C4A—C5A—C6A—C7A | 177.81 (17) | C2B—C1B—C6B—C7B | −173.44 (16) |
C18A—C5A—C6A—C7A | 60.7 (2) | C10B—C1B—C6B—C7B | −58.2 (2) |
C19A—C5A—C6A—C1A | 74.6 (2) | C17B—C1B—C6B—C5B | −69.5 (2) |
C4A—C5A—C6A—C1A | −49.3 (2) | C2B—C1B—C6B—C5B | 51.0 (2) |
C18A—C5A—C6A—C1A | −166.34 (18) | C10B—C1B—C6B—C5B | 166.16 (16) |
C1A—C6A—C7A—C8A | 64.1 (2) | C5B—C6B—C7B—C8B | −159.46 (16) |
C5A—C6A—C7A—C8A | −160.33 (16) | C1B—C6B—C7B—C8B | 64.0 (2) |
C6A—C7A—C8A—C9A | −58.6 (2) | C6B—C7B—C8B—C9B | −58.3 (2) |
C7A—C8A—C9A—C14A | −77.8 (2) | C7B—C8B—C9B—C14B | −78.8 (2) |
C7A—C8A—C9A—C10A | 49.1 (2) | C7B—C8B—C9B—C10B | 48.9 (2) |
C7A—C8A—C9A—C15A | 170.79 (18) | C7B—C8B—C9B—C15B | 169.71 (17) |
C8A—C9A—C10A—C11A | 179.42 (16) | C8B—C9B—C10B—C11B | 179.39 (16) |
C14A—C9A—C10A—C11A | −52.9 (2) | C14B—C9B—C10B—C11B | −52.2 (2) |
C15A—C9A—C10A—C11A | 56.9 (2) | C15B—C9B—C10B—C11B | 57.5 (2) |
C8A—C9A—C10A—C1A | −46.8 (2) | C8B—C9B—C10B—C1B | −47.1 (2) |
C14A—C9A—C10A—C1A | 80.9 (2) | C14B—C9B—C10B—C1B | 81.2 (2) |
C15A—C9A—C10A—C1A | −169.28 (15) | C15B—C9B—C10B—C1B | −169.00 (16) |
C17A—C1A—C10A—C11A | 56.7 (2) | C17B—C1B—C10B—C11B | 56.6 (2) |
C2A—C1A—C10A—C11A | −62.3 (2) | C2B—C1B—C10B—C11B | −62.8 (2) |
C6A—C1A—C10A—C11A | −178.05 (17) | C6B—C1B—C10B—C11B | −178.11 (16) |
C17A—C1A—C10A—C9A | −74.7 (2) | C17B—C1B—C10B—C9B | −74.5 (2) |
C2A—C1A—C10A—C9A | 166.34 (16) | C2B—C1B—C10B—C9B | 166.07 (16) |
C6A—C1A—C10A—C9A | 50.6 (2) | C6B—C1B—C10B—C9B | 50.8 (2) |
C9A—C10A—C11A—C12A | 38.2 (2) | C9B—C10B—C11B—C12B | 37.4 (2) |
C1A—C10A—C11A—C12A | −96.3 (2) | C1B—C10B—C11B—C12B | −97.0 (2) |
C10A—C11A—C12A—C13A | −42.8 (2) | C10B—C11B—C12B—C13B | −43.0 (2) |
C11A—C12A—C13A—O2A | −176.78 (17) | C11B—C12B—C13B—O2B | −174.73 (17) |
C11A—C12A—C13A—C16A | −50.4 (2) | C11B—C12B—C13B—C16B | −49.5 (2) |
C11A—C12A—C13A—C14A | 60.3 (2) | C11B—C12B—C13B—C14B | 61.0 (2) |
O2A—C13A—C14A—C9A | 164.88 (16) | O2B—C13B—C14B—C9B | 169.23 (17) |
C16A—C13A—C14A—C9A | 43.90 (19) | C16B—C13B—C14B—C9B | 43.30 (19) |
C12A—C13A—C14A—C9A | −71.85 (19) | C12B—C13B—C14B—C9B | −71.85 (19) |
C8A—C9A—C14A—C13A | −163.74 (16) | C8B—C9B—C14B—C13B | −163.31 (16) |
C10A—C9A—C14A—C13A | 69.79 (19) | C10B—C9B—C14B—C13B | 69.69 (19) |
C15A—C9A—C14A—C13A | −45.92 (19) | C15B—C9B—C14B—C13B | −45.50 (19) |
C8A—C9A—C15A—C16A | 150.37 (19) | C8B—C9B—C15B—C16B | 150.98 (18) |
C14A—C9A—C15A—C16A | 30.6 (2) | C14B—C9B—C15B—C16B | 31.0 (2) |
C10A—C9A—C15A—C16A | −86.92 (19) | C10B—C9B—C15B—C16B | −86.9 (2) |
C9A—C15A—C16A—C20A | 178.2 (2) | C9B—C15B—C16B—C20B | 176.3 (2) |
C9A—C15A—C16A—C13A | −4.4 (2) | C9B—C15B—C16B—C13B | −4.9 (2) |
O2A—C13A—C16A—C20A | 33.5 (3) | O2B—C13B—C16B—C20B | 29.1 (3) |
C14A—C13A—C16A—C20A | 153.3 (2) | C12B—C13B—C16B—C20B | −91.0 (3) |
C12A—C13A—C16A—C20A | −92.2 (3) | C14B—C13B—C16B—C20B | 155.2 (2) |
O2A—C13A—C16A—C15A | −144.01 (19) | O2B—C13B—C16B—C15B | −149.72 (19) |
C14A—C13A—C16A—C15A | −24.2 (2) | C12B—C13B—C16B—C15B | 90.1 (2) |
C12A—C13A—C16A—C15A | 90.3 (2) | C14B—C13B—C16B—C15B | −23.7 (2) |
C4A—C5A—C19A—O1A | −65.0 (2) | C4B—C5B—C19B—O1B | −67.2 (2) |
C18A—C5A—C19A—O1A | 52.7 (2) | C18B—C5B—C19B—O1B | 51.3 (3) |
C6A—C5A—C19A—O1A | 172.30 (19) | C6B—C5B—C19B—O1B | 171.42 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1AA···O2Bi | 0.81 (3) | 1.94 (3) | 2.750 (2) | 171 (4) |
O2A—H2AA···O1B | 0.86 (4) | 1.86 (4) | 2.711 (2) | 172 (3) |
O1B—H1BA···O1Aii | 0.88 (4) | 1.85 (4) | 2.718 (3) | 172 (3) |
O2B—H2BA···O2Aiii | 0.79 (4) | 1.95 (4) | 2.699 (2) | 159 (3) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, y−1/2, −z+1; (iii) −x+1, y−1/2, −z+2. |