Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name J.M.Winne 'P.J.De Clercq' M.Milanesio P.Pattison D.Viterbo _publ_contact_author_name 'Pierre De Clerq' _publ_contact_author_email PIERRE.DECLERCQ@UGENT.BE data_declsmal _database_code_depnum_ccdc_archive 'CCDC 675998' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '(9alpha,13beta)-delta17,20-Protolanostane Alcohol' _chemical_melting_point ? _chemical_formula_moiety '2(C25 H40 O) (CH4O)' _chemical_formula_sum 'C51 H84 O3' _chemical_formula_weight 745.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.429(1) _cell_length_b 13.631(2) _cell_length_c 50.896(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4460.2 _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Very thin plate' _exptl_crystal_colour 'Uncoloured and transparent' _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.040 _exptl_crystal_size_min 0.005 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.104 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type 'SADABS.[G.M. Sheldrick, SADABS, University of Gottingen, Germany, 1996' _exptl_absorpt_correction_T_min 0.882 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.7114(1) _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MAR345 CCD on synchrotron beamline (SNBL at ESRF)' _diffrn_measurement_method 'Phi rotation' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3482 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 17.23 _diffrn_measured_fraction_theta_max 0.787 _diffrn_reflns_theta_full 17.23 _diffrn_measured_fraction_theta_full 0.787 _reflns_number_total 2006 _reflns_number_gt 1637 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro 171.30.3' _computing_cell_refinement 'CrysAlisPro 171.30.3' _computing_data_reduction 'CrysAlisPro 171.30.3' _computing_structure_solution 'SIR2002 (Burla, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'MOLDRAW (Ugliengo, 1993)' _computing_publication_material 'MOLDRAW (Ugliengo, 1993)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Some restrains were employed to obtain a more stable refinement. They were applied to the more mobile >C=C(CH3)2 moiety bonded to the D-ring where no H-bonds are present and the crystal packing is governed by weak hydrophobic interactions only and where the larger amount of disorder was found. Ten geometric restrains on bond distances were used to impose similar geometries of the C=C(CH3)2 bonded to the D-ring belonging to the two molecules in the asymmetric unit. The restrains were: sadi 0.02 c34 c43 c34 c40 c49 c48 c49 c50 (C-CH3 bonds) sadi 0.02 c45 c49 c22 c34 (C=C bonds) sadi 0.02 c22 C38 c45 C47 (C-C bonds adjacent to C=C) sadi 0.02 c18 c22 c42 c45 (C-C bonds adjacent to C=C) Two restrain on the ADP parameters were adopted: Same ADP for the four CH3 group in the =C(CH3)2 moiety eadp C40 C43 C48 C50 Same ADP for the two C atoms bearing the methyl groups in the =C(CH3)2 moiety eadp c34 c49 ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.6000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 2006 _refine_ls_number_parameters 213 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.2217 _refine_ls_R_factor_gt 0.2009 _refine_ls_wR_factor_ref 0.5641 _refine_ls_wR_factor_gt 0.5235 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.597 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.125 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -1.157(3) -0.7498(10) -0.2124(4) 0.078(5) Uiso 1 1 d . . . H1A H -1.2697 -0.7607 -0.2193 0.117 Uiso 1 1 calc R . . O2 O -0.493(3) -0.2874(12) -0.2598(4) 0.092(6) Uiso 1 1 d . . . H2A H -0.3810 -0.3160 -0.2589 0.138 Uiso 1 1 calc R . . C1 C -0.656(3) -0.0811(15) -0.1428(5) 0.051(6) Uiso 1 1 d . . . C2 C -0.507(3) -0.1459(14) -0.1949(5) 0.050(6) Uiso 1 1 d . . . H2 H -0.6477 -0.1210 -0.1980 0.060 Uiso 1 1 calc R . . C3 C -0.417(4) -0.1812(17) -0.2235(6) 0.071(8) Uiso 1 1 d . . . C4 C -0.792(4) -0.0052(17) -0.1589(6) 0.083(8) Uiso 1 1 d . . . H4A H -0.7636 -0.0126 -0.1773 0.124 Uiso 1 1 calc R . . H4B H -0.7579 0.0604 -0.1535 0.124 Uiso 1 1 calc R . . H4C H -0.9369 -0.0173 -0.1557 0.124 Uiso 1 1 calc R . . C5 C -0.390(3) -0.0651(14) -0.1821(5) 0.050(6) Uiso 1 1 d . . . H5A H -0.2426 -0.0782 -0.1839 0.060 Uiso 1 1 calc R . . H5B H -0.4195 -0.0047 -0.1915 0.060 Uiso 1 1 calc R . . C6 C -0.649(4) -0.2600(17) -0.1075(6) 0.072(8) Uiso 1 1 d . . . H6 H -0.6397 -0.3145 -0.0965 0.087 Uiso 1 1 calc R . . C7 C -1.430(14) -0.516(5) -0.0560(19) 0.27(3) Uiso 1 1 d . . . H7A H -1.4945 -0.4520 -0.0567 0.328 Uiso 1 1 calc R . . H7B H -1.5194 -0.5649 -0.0643 0.328 Uiso 1 1 calc R . . C8 C -0.561(3) -0.2575(14) -0.2329(5) 0.049(6) Uiso 1 1 d . . . H8A H -0.7019 -0.2302 -0.2338 0.059 Uiso 1 1 calc R . . C9 C -0.530(3) -0.2341(14) -0.1760(5) 0.053(6) Uiso 1 1 d . . . C10 C -0.684(4) -0.0746(16) -0.1147(6) 0.061(7) Uiso 1 1 d . . . C11 C -1.170(4) -0.8121(15) -0.1677(6) 0.067(7) Uiso 1 1 d . . . H11A H -1.0295 -0.8380 -0.1678 0.081 Uiso 1 1 calc R . . H11B H -1.2653 -0.8632 -0.1733 0.081 Uiso 1 1 calc R . . C12 C -0.696(3) -0.1972(13) -0.1529(5) 0.046(6) Uiso 1 1 d . . . H12 H -0.8354 -0.1993 -0.1607 0.056 Uiso 1 1 calc R . . C13 C -0.567(4) -0.3579(14) -0.2171(5) 0.055(6) Uiso 1 1 d . . . H13A H -0.4304 -0.3882 -0.2162 0.066 Uiso 1 1 calc R . . H13B H -0.6651 -0.4038 -0.2247 0.066 Uiso 1 1 calc R . . C14 C -1.097(3) -0.6069(12) -0.1506(5) 0.036(5) Uiso 1 1 d . . . H14 H -1.2370 -0.5783 -0.1513 0.043 Uiso 1 1 calc R . . C15 C -0.645(4) -0.3188(15) -0.1879(5) 0.057(7) Uiso 1 1 d . . . H15A H -0.7900 -0.3006 -0.1893 0.069 Uiso 1 1 calc R . . H15B H -0.6364 -0.3735 -0.1758 0.069 Uiso 1 1 calc R . . C16 C -1.102(4) -0.6966(15) -0.1277(6) 0.062(7) Uiso 1 1 d . . . C17 C -0.692(3) -0.2696(15) -0.1321(6) 0.056(6) Uiso 1 1 d . . . H17 H -0.7259 -0.3330 -0.1373 0.067 Uiso 1 1 calc R . . C18 C -0.613(4) -0.1547(16) -0.0966(5) 0.063(7) Uiso 1 1 d D . . H18 H -0.4640 -0.1462 -0.0936 0.076 Uiso 1 1 calc R . . C19 C -0.436(3) -0.0495(13) -0.1541(4) 0.039(5) Uiso 1 1 d . . . H19A H -0.4183 0.0198 -0.1505 0.047 Uiso 1 1 calc R . . H19B H -0.3307 -0.0841 -0.1441 0.047 Uiso 1 1 calc R . . C20 C -0.594(4) 0.0215(17) -0.1036(6) 0.073(8) Uiso 1 1 d . . . H20A H -0.6205 0.0248 -0.0850 0.110 Uiso 1 1 calc R . . H20B H -0.6576 0.0765 -0.1121 0.110 Uiso 1 1 calc R . . H20C H -0.4462 0.0230 -0.1066 0.110 Uiso 1 1 calc R . . C21 C -1.187(4) -0.7212(15) -0.1858(5) 0.063(7) Uiso 1 1 d . . . H21A H -1.3296 -0.6959 -0.1842 0.075 Uiso 1 1 calc R . . C22 C -0.728(5) -0.137(2) -0.0701(6) 0.103(10) Uiso 1 1 d D . . C23 C -0.451(4) -0.0883(16) -0.2420(5) 0.069(7) Uiso 1 1 d . . . H23A H -0.5946 -0.0698 -0.2418 0.103 Uiso 1 1 calc R . . H23B H -0.4100 -0.1044 -0.2597 0.103 Uiso 1 1 calc R . . H23C H -0.3673 -0.0347 -0.2358 0.103 Uiso 1 1 calc R . . C24 C -0.340(3) -0.2695(14) -0.1639(5) 0.048(6) Uiso 1 1 d . . . H24A H -0.2676 -0.2157 -0.1558 0.073 Uiso 1 1 calc R . . H24B H -0.2522 -0.2986 -0.1770 0.073 Uiso 1 1 calc R . . H24C H -0.3729 -0.3178 -0.1508 0.073 Uiso 1 1 calc R . . C25 C -0.920(5) -0.066(2) -0.1051(7) 0.100(9) Uiso 1 1 d . . . H25A H -0.9705 0.0003 -0.1078 0.120 Uiso 1 1 calc R . . H25B H -1.0073 -0.1106 -0.1150 0.120 Uiso 1 1 calc R . . C26 C -1.042(3) -0.6399(15) -0.1790(5) 0.058(6) Uiso 1 1 d . . . C27 C -0.941(5) -0.522(2) -0.1390(7) 0.106(10) Uiso 1 1 d . . . H27A H -0.7976 -0.5405 -0.1422 0.127 Uiso 1 1 calc R . . H27B H -0.9675 -0.4603 -0.1478 0.127 Uiso 1 1 calc R . . C28 C -0.198(4) -0.2067(16) -0.2240(6) 0.075(8) Uiso 1 1 d . . . H28A H -0.1177 -0.1536 -0.2168 0.112 Uiso 1 1 calc R . . H28B H -0.1549 -0.2185 -0.2418 0.112 Uiso 1 1 calc R . . H28C H -0.1753 -0.2648 -0.2137 0.112 Uiso 1 1 calc R . . C29 C -1.192(5) -0.734(2) -0.0854(8) 0.109(10) Uiso 1 1 d . . . H29 H -1.2468 -0.7956 -0.0887 0.130 Uiso 1 1 calc R . . C30 C -1.168(5) -0.518(2) -0.0686(8) 0.100(9) Uiso 1 1 d . . . C31 C -1.074(6) -0.421(2) -0.0580(8) 0.113(11) Uiso 1 1 d . . . H31A H -1.0926 -0.4182 -0.0393 0.170 Uiso 1 1 calc R . . H31B H -1.1423 -0.3661 -0.0660 0.170 Uiso 1 1 calc R . . H31C H -0.9280 -0.4189 -0.0620 0.170 Uiso 1 1 calc R . . C32 C -1.150(4) -0.5387(17) -0.0982(6) 0.072(8) Uiso 1 1 d . . . C33 C -1.206(4) -0.6483(15) -0.1041(5) 0.062(7) Uiso 1 1 d . . . H33 H -1.3538 -0.6461 -0.1089 0.074 Uiso 1 1 calc R . . C34 C -0.657(5) -0.180(2) -0.0465(7) 0.115(8) Uiso 1 1 d D . . C35 C -1.229(3) -0.7727(14) -0.1398(5) 0.050(6) Uiso 1 1 d . . . H35A H -1.3705 -0.7480 -0.1408 0.060 Uiso 1 1 calc R . . H35B H -1.2312 -0.8284 -0.1280 0.060 Uiso 1 1 calc R . . C36 C -0.978(4) -0.5092(18) -0.1078(6) 0.079(8) Uiso 1 1 d . . . H36A H -0.8670 -0.5435 -0.0987 0.095 Uiso 1 1 calc R . . H36B H -0.9637 -0.4401 -0.1036 0.095 Uiso 1 1 calc R . . C37 C -1.073(5) -0.542(2) -0.1939(7) 0.109(10) Uiso 1 1 d . . . H37A H -1.2118 -0.5182 -0.1912 0.164 Uiso 1 1 calc R . . H37B H -1.0501 -0.5521 -0.2124 0.164 Uiso 1 1 calc R . . H37C H -0.9751 -0.4941 -0.1875 0.164 Uiso 1 1 calc R . . C38 C -0.929(5) -0.092(2) -0.0758(7) 0.110(10) Uiso 1 1 d D . . H38A H -0.9497 -0.0332 -0.0652 0.133 Uiso 1 1 calc R . . H38B H -1.0418 -0.1373 -0.0723 0.133 Uiso 1 1 calc R . . C39 C -0.905(4) -0.7280(19) -0.1222(6) 0.091(9) Uiso 1 1 d . . . H39A H -0.8238 -0.6740 -0.1158 0.136 Uiso 1 1 calc R . . H39B H -0.8427 -0.7536 -0.1379 0.136 Uiso 1 1 calc R . . H39C H -0.9103 -0.7786 -0.1091 0.136 Uiso 1 1 calc R . . C40 C -0.802(7) -0.166(3) -0.0250(9) 0.157(8) Uiso 1 1 d D . . H40A H -0.7467 -0.1943 -0.0093 0.235 Uiso 1 1 calc R . . H40B H -0.9325 -0.1964 -0.0293 0.235 Uiso 1 1 calc R . . H40C H -0.8244 -0.0966 -0.0223 0.235 Uiso 1 1 calc R . . C41 C -0.842(6) -0.661(3) -0.1847(9) 0.140(14) Uiso 1 1 d . . . H41A H -0.7546 -0.6081 -0.1791 0.210 Uiso 1 1 calc R . . H41B H -0.8274 -0.6701 -0.2033 0.210 Uiso 1 1 calc R . . H41C H -0.8020 -0.7202 -0.1758 0.210 Uiso 1 1 calc R . . C42 C -1.035(5) -0.5927(19) -0.0498(6) 0.093(9) Uiso 1 1 d D . . H42 H -0.8875 -0.5757 -0.0488 0.112 Uiso 1 1 calc R . . C43 C -0.454(6) -0.222(3) -0.0448(10) 0.157(8) Uiso 1 1 d D . . H43A H -0.4307 -0.2458 -0.0273 0.235 Uiso 1 1 calc R . . H43B H -0.3517 -0.1737 -0.0491 0.235 Uiso 1 1 calc R . . H43C H -0.4443 -0.2760 -0.0570 0.235 Uiso 1 1 calc R . . C44 C -1.316(6) -0.474(3) -0.1089(9) 0.138(13) Uiso 1 1 d . . . H44A H -1.4487 -0.4945 -0.1024 0.207 Uiso 1 1 calc R . . H44B H -1.3156 -0.4777 -0.1278 0.207 Uiso 1 1 calc R . . H44C H -1.2900 -0.4074 -0.1036 0.207 Uiso 1 1 calc R . . C45 C -1.151(6) -0.581(3) -0.0228(8) 0.141(13) Uiso 1 1 d D . . C46 C -1.075(7) -0.704(3) -0.0600(10) 0.158(15) Uiso 1 1 d . . . H46 H -1.0218 -0.7546 -0.0497 0.189 Uiso 1 1 calc R . . C47 C -1.361(7) -0.546(3) -0.0275(11) 0.166(16) Uiso 1 1 d D . . H47A H -1.3837 -0.4898 -0.0163 0.199 Uiso 1 1 calc R . . H47B H -1.4553 -0.5972 -0.0216 0.199 Uiso 1 1 calc R . . C48 C -0.873(6) -0.621(3) -0.0001(11) 0.157(8) Uiso 1 1 d D . . H48A H -0.8061 -0.6214 0.0168 0.235 Uiso 1 1 calc R . . H48B H -0.8125 -0.5709 -0.0109 0.235 Uiso 1 1 calc R . . H48C H -0.8539 -0.6838 -0.0084 0.235 Uiso 1 1 calc R . . C49 C -1.091(5) -0.602(2) 0.0032(7) 0.115(8) Uiso 1 1 d D . . C50 C -1.213(7) -0.601(3) 0.0268(9) 0.157(8) Uiso 1 1 d D . . H50A H -1.3418 -0.5677 0.0236 0.235 Uiso 1 1 calc R . . H50B H -1.1378 -0.5681 0.0405 0.235 Uiso 1 1 calc R . . H50C H -1.2415 -0.6675 0.0322 0.235 Uiso 1 1 calc R . . O3 O -0.840(3) 0.1180(11) -0.2227(4) 0.088(6) Uiso 1 1 d . . . C51 C -0.994(9) 0.088(4) -0.2329(12) 0.182(19) Uiso 1 1 d . . . _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C21 1.43(3) . ? O2 C8 1.50(3) . ? C1 C10 1.44(3) . ? C1 C4 1.58(4) . ? C1 C19 1.59(3) . ? C1 C12 1.68(3) . ? C2 C5 1.48(3) . ? C2 C9 1.55(3) . ? C2 C3 1.64(4) . ? C3 C28 1.45(4) . ? C3 C8 1.47(3) . ? C3 C23 1.59(4) . ? C5 C19 1.47(3) . ? C6 C17 1.29(3) . ? C6 C18 1.55(3) . ? C7 C47 1.57(9) . ? C7 C30 1.81(10) . ? C8 C13 1.59(3) . ? C9 C24 1.45(3) . ? C9 C15 1.50(3) . ? C9 C12 1.66(3) . ? C10 C18 1.50(4) . ? C10 C20 1.54(3) . ? C10 C25 1.60(4) . ? C11 C21 1.55(4) . ? C11 C35 1.56(4) . ? C12 C17 1.45(3) . ? C13 C15 1.65(3) . ? C14 C26 1.55(3) . ? C14 C27 1.64(4) . ? C14 C16 1.69(4) . ? C16 C39 1.37(3) . ? C16 C35 1.46(3) . ? C16 C33 1.52(4) . ? C18 C22 1.56(3) . ? C21 C26 1.49(3) . ? C22 C34 1.41(4) . ? C22 C38 1.46(4) . ? C25 C38 1.53(5) . ? C26 C41 1.35(4) . ? C26 C37 1.55(4) . ? C27 C36 1.62(4) . ? C29 C33 1.50(4) . ? C29 C46 1.55(6) . ? C30 C32 1.54(4) . ? C30 C31 1.55(4) . ? C30 C42 1.64(5) . ? C32 C36 1.28(3) . ? C32 C44 1.49(4) . ? C32 C33 1.57(3) . ? C34 C43 1.43(3) . ? C34 C40 1.45(3) . ? C42 C45 1.57(4) . ? C42 C46 1.62(5) . ? C45 C49 1.41(4) . ? C45 C47 1.45(4) . ? C48 C49 1.43(3) . ? C49 C50 1.44(3) . ? O3 C51 1.19(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C1 C4 114(2) . . ? C10 C1 C19 117(2) . . ? C4 C1 C19 97(2) . . ? C10 C1 C12 110(1) . . ? C4 C1 C12 112(2) . . ? C19 C1 C12 106(2) . . ? C5 C2 C9 111(2) . . ? C5 C2 C3 115(2) . . ? C9 C2 C3 111(2) . . ? C28 C3 C8 116(2) . . ? C28 C3 C23 108(2) . . ? C8 C3 C23 107(2) . . ? C28 C3 C2 115(2) . . ? C8 C3 C2 106(2) . . ? C23 C3 C2 104(2) . . ? C19 C5 C2 115(2) . . ? C17 C6 C18 118(2) . . ? C47 C7 C30 94(5) . . ? C3 C8 O2 108(2) . . ? C3 C8 C13 117(2) . . ? O2 C8 C13 104(2) . . ? C24 C9 C15 109(2) . . ? C24 C9 C2 116(2) . . ? C15 C9 C2 113(2) . . ? C24 C9 C12 110(2) . . ? C15 C9 C12 102(2) . . ? C2 C9 C12 105(1) . . ? C1 C10 C18 122(2) . . ? C1 C10 C20 112(2) . . ? C18 C10 C20 106(2) . . ? C1 C10 C25 115(2) . . ? C18 C10 C25 99(2) . . ? C20 C10 C25 101(2) . . ? C21 C11 C35 104(2) . . ? C17 C12 C9 107() . . ? C17 C12 C1 114(2) . . ? C9 C12 C1 114(1) . . ? C8 C13 C15 100(2) . . ? C26 C14 C27 114(2) . . ? C26 C14 C16 116(1) . . ? C27 C14 C16 106(2) . . ? C9 C15 C13 118(2) . . ? C39 C16 C35 112(2) . . ? C39 C16 C33 113(3) . . ? C35 C16 C33 113(2) . . ? C39 C16 C14 110(2) . . ? C35 C16 C14 103(2) . . ? C33 C16 C14 104(2) . . ? C6 C17 C12 130(2) . . ? C10 C18 C6 114(2) . . ? C10 C18 C22 106(2) . . ? C6 C18 C22 113(2) . . ? C5 C19 C1 119(2) . . ? O1 C21 C26 110(2) . . ? O1 C21 C11 110(2) . . ? C26 C21 C11 114(2) . . ? C34 C22 C38 129(3) . . ? C34 C22 C18 121(2) . . ? C38 C22 C18 108(3) . . ? C38 C25 C10 109(3) . . ? C41 C26 C21 113(2) . . ? C41 C26 C37 101(3) . . ? C21 C26 C37 117(2) . . ? C41 C26 C14 119(3) . . ? C21 C26 C14 107(2) . . ? C37 C26 C14 100(2) . . ? C36 C27 C14 110(2) . . ? C33 C29 C46 111(3) . . ? C32 C30 C31 118(3) . . ? C32 C30 C42 115(2) . . ? C31 C30 C42 97(3) . . ? C32 C30 C7 115(4) . . ? C31 C30 C7 104(4) . . ? C42 C30 C7 106(4) . . ? C36 C32 C44 107(3) . . ? C36 C32 C30 112(3) . . ? C44 C32 C30 101(3) . . ? C36 C32 C33 115(2) . . ? C44 C32 C33 109(2) . . ? C30 C32 C33 110(2) . . ? C29 C33 C16 98(2) . . ? C29 C33 C32 127(3) . . ? C16 C33 C32 117(2) . . ? C22 C34 C43 121(3) . . ? C22 C34 C40 112(3) . . ? C43 C34 C40 127(4) . . ? C16 C35 C11 120(2) . . ? C32 C36 C27 118(3) . . ? C22 C38 C25 105(3) . . ? C45 C42 C46 108(3) . . ? C45 C42 C30 102(3) . . ? C46 C42 C30 108(3) . . ? C49 C45 C47 119(4) . . ? C49 C45 C42 132(3) . . ? C47 C45 C42 109(4) . . ? C29 C46 C42 126(4) . . ? C45 C47 C7 120(5) . . ? C45 C49 C48 101(4) . . ? C45 C49 C50 129(3) . . ? C48 C49 C50 129(4) . . ? #####