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
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.108
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 26
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 29.55 From the CIF: _reflns_number_total 5031 Count of symmetry unique reflns 5037 Completeness (_total/calc) 99.88% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1B = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5B = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6B = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9B = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10B = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13B = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 13 ALERT level G = General alerts; check 13 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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. |
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