# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Rosa Santillan' 'Ricardo Cruz' 'Norberto Farfan' 'Blas Flores' 'Miguel A Garcia-Garibay' 'Arturo Pozos' 'Braulio Rodriguez-Molina' 'Margarita Romero' _publ_contact_author_name 'Rosa Santillan' _publ_contact_author_email RSANTILL@CINVESTAV.MX _publ_section_title ; Synthesis and Solid State Characterization of Molecular Rotors with Steroidal Stators: Ethisterone and Norethisterone ; _publ_requested_category FO # Attachment 'Steroidal_rotor.cif' data_Compound1 _database_code_depnum_ccdc_archive 'CCDC 768383' #TrackingRef 'Steroidal_rotor.cif' _audit_creation_date 2009-12-19T22:39:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1,4-bis(19-nor-17a-ethynyltestosterone-17b-acetate)phenylene ; _chemical_name_common ? _chemical_formula_moiety 'C50 H58 O6, 2(C H Cl3)' _chemical_formula_sum 'C52 H60 Cl6 O6' _chemical_formula_weight 993.70 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall 'C2 y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 19.2269(6) _cell_length_b 10.7806(4) _cell_length_c 12.2170(4) _cell_angle_alpha 90 _cell_angle_beta 94.896(3) _cell_angle_gamma 90 _cell_volume 2523.07(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9786 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.103 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.175 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.3 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044.0 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.388 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.792779E-1 _diffrn_orient_matrix_ub_12 0.301469E-1 _diffrn_orient_matrix_ub_13 -0.472761E-1 _diffrn_orient_matrix_ub_21 0.679062E-1 _diffrn_orient_matrix_ub_22 0.424515E-1 _diffrn_orient_matrix_ub_23 0.662782E-1 _diffrn_orient_matrix_ub_31 -0.18945E-2 _diffrn_orient_matrix_ub_32 -0.928273E-1 _diffrn_orient_matrix_ub_33 0.110116E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0679 _diffrn_reflns_av_unetI/netI 0.0844 _diffrn_reflns_number 15648 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.72 _diffrn_reflns_theta_max 27.15 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 5379 _reflns_number_gt 3144 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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. ; _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^)+(0.0801P)^2^+1.3026P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5379 _refine_ls_number_parameters 291 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.127 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.18 _refine_ls_wR_factor_gt 0.1451 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.09(11) _refine_diff_density_max 0.189 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C3 C 0.30620(18) 0.3784(4) 0.3482(3) 0.0463(8) Uani 1 1 d . . . C4 C 0.2622(3) 0.1669(6) 0.0524(4) 0.0913(17) Uani 1 1 d . . . H4A H 0.2204 0.1748 0.004 0.137 Uiso 1 1 calc R . . H4B H 0.2591 0.0941 0.0971 0.137 Uiso 1 1 calc R . . H4C H 0.3017 0.16 0.0099 0.137 Uiso 1 1 calc R . . C7 C 0.12036(19) 0.4453(3) 0.5214(3) 0.0437(8) Uani 1 1 d . . . H7 H 0.0747 0.4225 0.4852 0.052 Uiso 1 1 calc R . . C8 C 0.14228(18) 0.3456(4) 0.6068(3) 0.0458(9) Uani 1 1 d . . . H8 H 0.1866 0.3727 0.6449 0.055 Uiso 1 1 calc R . . C11 C 0.23461(17) 0.3641(4) 0.2953(3) 0.0476(9) Uani 1 1 d . . . C12 C 0.18193(18) 0.3243(3) 0.3777(3) 0.0450(9) Uani 1 1 d . . . C13 C 0.1557(2) 0.2196(4) 0.5544(3) 0.0530(10) Uani 1 1 d . . . H13A H 0.1753 0.1633 0.6107 0.064 Uiso 1 1 calc R . . H13B H 0.1116 0.1852 0.524 0.064 Uiso 1 1 calc R . . C15 C 0.17236(18) 0.4497(3) 0.4354(3) 0.0419(8) Uani 1 1 d . . . H15 H 0.2176 0.4707 0.4738 0.05 Uiso 1 1 calc R . . C17 C 0.2056(2) 0.2288(4) 0.4631(3) 0.0527(9) Uani 1 1 d . . . H17A H 0.2519 0.2506 0.4953 0.063 Uiso 1 1 calc R . . H17B H 0.2087 0.1486 0.4279 0.063 Uiso 1 1 calc R . . C18 C 0.0757(2) 0.4602(4) 0.7452(3) 0.0531(10) Uani 1 1 d . . . C19 C 0.0893(2) 0.3340(4) 0.6946(3) 0.0528(10) Uani 1 1 d . . . H19 H 0.0451 0.3053 0.6573 0.063 Uiso 1 1 calc R . . C20 C 0.1608(2) 0.5402(4) 0.3386(3) 0.0548(10) Uani 1 1 d . . . H20A H 0.1758 0.623 0.3606 0.066 Uiso 1 1 calc R . . H20B H 0.1118 0.5431 0.312 0.066 Uiso 1 1 calc R . . C24 C 0.2050(2) 0.4898(4) 0.2492(3) 0.0531(9) Uani 1 1 d . . . H24A H 0.2425 0.5467 0.2365 0.064 Uiso 1 1 calc R . . H24B H 0.1764 0.4774 0.1808 0.064 Uiso 1 1 calc R . . C28 C 0.0613(2) 0.5631(4) 0.6648(4) 0.0643(11) Uani 1 1 d . . . H28A H 0.0618 0.6411 0.7044 0.077 Uiso 1 1 calc R . . H28B H 0.0148 0.5521 0.6286 0.077 Uiso 1 1 calc R . . C29 C 0.43265(18) 0.4013(3) 0.4471(3) 0.0471(9) Uani 1 1 d . . . C33 C 0.1133(2) 0.5704(4) 0.5779(3) 0.0578(10) Uani 1 1 d . . . H33A H 0.1585 0.5958 0.612 0.069 Uiso 1 1 calc R . . H33B H 0.0979 0.6324 0.5236 0.069 Uiso 1 1 calc R . . C34 C 0.4436(2) 0.4034(5) 0.5607(3) 0.0669(13) Uani 1 1 d . . . H34 H 0.4055 0.405 0.6028 0.08 Uiso 1 1 calc R . . C35 C 0.36297(19) 0.3922(4) 0.3928(3) 0.0477(8) Uani 1 1 d . . . C36 C 0.11402(19) 0.2799(4) 0.3127(3) 0.0587(10) Uani 1 1 d . . . H36A H 0.1233 0.206 0.2725 0.088 Uiso 1 1 calc R . . H36B H 0.0971 0.3436 0.2624 0.088 Uiso 1 1 calc R . . H36C H 0.0795 0.2624 0.3628 0.088 Uiso 1 1 calc R . . C42 C 0.1121(3) 0.2376(5) 0.7835(4) 0.0763(14) Uani 1 1 d . . . H42A H 0.1054 0.155 0.7529 0.092 Uiso 1 1 calc R . . H42B H 0.1614 0.2481 0.8052 0.092 Uiso 1 1 calc R . . C43 C 0.0742(2) 0.4765(6) 0.8529(4) 0.0749(14) Uani 1 1 d . . . H43 H 0.0697 0.5569 0.879 0.09 Uiso 1 1 calc R . . C46 C 0.4897(2) 0.4033(5) 0.3879(3) 0.0660(13) Uani 1 1 d . . . H46 H 0.4835 0.4045 0.3116 0.079 Uiso 1 1 calc R . . C48 C 0.2704(3) 0.2785(6) 0.1244(3) 0.0698(13) Uani 1 1 d . . . C53 C 0.1173(3) 0.8712(6) 0.1072(4) 0.0771(13) Uani 1 1 d . . . H53 H 0.1355 0.8756 0.0347 0.092 Uiso 1 1 calc R . . C54 C 0.0718(3) 0.2488(6) 0.8837(4) 0.0837(16) Uani 1 1 d . . . H54A H 0.0229 0.232 0.8634 0.1 Uiso 1 1 calc R . . H54B H 0.0888 0.1876 0.9377 0.1 Uiso 1 1 calc R . . C56 C 0.0794(2) 0.3752(7) 0.9327(4) 0.0836(15) Uani 1 1 d . . . Cl1 Cl 0.06455(11) 1.00052(18) 0.12385(14) 0.1182(6) Uani 1 1 d . . . Cl2 Cl 0.07285(11) 0.73313(19) 0.11706(17) 0.1252(7) Uani 1 1 d . . . Cl3 Cl 0.18779(8) 0.8750(2) 0.20816(13) 0.1210(6) Uani 1 1 d . . . O1 O 0.0859(2) 0.3934(6) 1.0315(3) 0.1318(19) Uani 1 1 d . . . O3 O 0.23493(13) 0.2643(3) 0.2131(2) 0.0569(7) Uani 1 1 d . . . O6 O 0.3026(2) 0.3712(4) 0.1061(3) 0.0896(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C3 0.042(2) 0.046(2) 0.0506(18) 0.0059(18) 0.0062(16) 0.0006(18) C4 0.106(4) 0.097(4) 0.074(3) -0.027(3) 0.020(3) -0.008(3) C7 0.0378(18) 0.043(2) 0.0489(18) 0.0031(16) -0.0022(15) 0.0010(15) C8 0.0358(18) 0.051(2) 0.0504(19) 0.0068(17) 0.0036(15) -0.0076(16) C11 0.0387(18) 0.060(2) 0.0442(17) -0.0028(19) 0.0016(14) -0.0020(19) C12 0.0354(19) 0.050(2) 0.0487(19) -0.0016(17) 0.0017(16) -0.0004(16) C13 0.055(2) 0.044(2) 0.061(2) 0.0107(18) 0.0076(18) -0.0004(18) C15 0.0359(18) 0.043(2) 0.0458(18) 0.0067(16) -0.0009(15) 0.0001(15) C17 0.052(2) 0.043(2) 0.064(2) 0.0038(19) 0.0093(19) 0.0051(17) C18 0.044(2) 0.066(3) 0.049(2) -0.0011(19) 0.0055(16) -0.0107(19) C19 0.043(2) 0.063(3) 0.052(2) 0.0099(19) 0.0028(17) -0.0051(18) C20 0.056(2) 0.054(3) 0.054(2) 0.0126(19) 0.0036(19) 0.0107(19) C24 0.053(2) 0.057(2) 0.0483(19) 0.0112(19) 0.0017(17) -0.002(2) C28 0.064(3) 0.064(3) 0.066(2) -0.009(2) 0.015(2) 0.005(2) C29 0.0382(18) 0.047(2) 0.055(2) 0.0033(18) 0.0029(15) 0.0006(16) C33 0.063(2) 0.054(3) 0.058(2) 0.001(2) 0.012(2) 0.001(2) C34 0.038(2) 0.102(4) 0.063(2) -0.002(2) 0.0134(18) 0.003(2) C35 0.040(2) 0.046(2) 0.0578(19) -0.0009(18) 0.0054(16) -0.0024(17) C36 0.040(2) 0.076(3) 0.061(2) -0.010(2) 0.0023(17) -0.012(2) C42 0.071(3) 0.086(4) 0.073(3) 0.029(3) 0.010(2) 0.002(3) C43 0.064(3) 0.093(4) 0.069(3) -0.016(3) 0.013(2) -0.013(3) C46 0.042(2) 0.102(4) 0.053(2) 0.000(2) 0.0030(17) -0.003(2) C48 0.062(3) 0.096(4) 0.053(2) -0.011(3) 0.010(2) -0.002(3) C53 0.080(3) 0.088(3) 0.066(2) 0.010(3) 0.022(2) 0.006(3) C54 0.072(3) 0.115(5) 0.065(3) 0.035(3) 0.008(2) -0.011(3) C56 0.064(3) 0.134(5) 0.053(3) 0.004(3) 0.004(2) -0.016(4) Cl1 0.1411(15) 0.1097(13) 0.1056(11) 0.0179(9) 0.0212(10) 0.0411(12) Cl2 0.1348(15) 0.1059(13) 0.1308(14) 0.0153(11) -0.0115(12) -0.0254(11) Cl3 0.0873(10) 0.1678(18) 0.1051(10) 0.0168(12) -0.0087(8) -0.0039(12) O1 0.129(3) 0.215(6) 0.0492(18) 0.010(3) -0.0090(18) -0.038(4) O3 0.0475(14) 0.0682(19) 0.0552(15) -0.0092(14) 0.0057(12) -0.0054(13) O6 0.101(2) 0.103(3) 0.0698(19) -0.009(2) 0.0351(18) -0.018(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 C35 1.187(5) . ? C3 C11 1.478(5) . ? C4 C48 1.491(7) . ? C4 H4A 0.96 . ? C4 H4B 0.96 . ? C4 H4C 0.96 . ? C7 C15 1.512(5) . ? C7 C33 1.527(5) . ? C7 C8 1.531(5) . ? C7 H7 0.98 . ? C8 C13 1.533(6) . ? C8 C19 1.547(5) . ? C8 H8 0.98 . ? C11 O3 1.473(5) . ? C11 C12 1.548(5) . ? C11 C24 1.557(6) . ? C12 C17 1.508(5) . ? C12 C15 1.542(5) . ? C12 C36 1.545(5) . ? C13 C17 1.536(5) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C15 C20 1.534(5) . ? C15 H15 0.98 . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? C18 C43 1.330(6) . ? C18 C28 1.491(6) . ? C18 C19 1.526(6) . ? C19 C42 1.539(6) . ? C19 H19 0.98 . ? C20 C24 1.539(6) . ? C20 H20A 0.97 . ? C20 H20B 0.97 . ? C24 H24A 0.97 . ? C24 H24B 0.97 . ? C28 C33 1.522(6) . ? C28 H28A 0.97 . ? C28 H28B 0.97 . ? C29 C46 1.365(5) . ? C29 C34 1.386(5) . ? C29 C35 1.447(5) . ? C33 H33A 0.97 . ? C33 H33B 0.97 . ? C34 C46 1.378(6) 2_656 ? C34 H34 0.93 . ? C36 H36A 0.96 . ? C36 H36B 0.96 . ? C36 H36C 0.96 . ? C42 C54 1.507(7) . ? C42 H42A 0.97 . ? C42 H42B 0.97 . ? C43 C56 1.461(8) . ? C43 H43 0.93 . ? C46 C34 1.378(6) 2_656 ? C46 H46 0.93 . ? C48 O6 1.207(6) . ? C48 O3 1.337(5) . ? C53 Cl2 1.726(6) . ? C53 Cl1 1.746(6) . ? C53 Cl3 1.753(5) . ? C53 H53 0.98 . ? C54 C56 1.491(9) . ? C54 H54A 0.97 . ? C54 H54B 0.97 . ? C56 O1 1.218(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 C35 C3 C11 178.1(4) . . ? C48 C4 H4A 109.5 . . ? C48 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C48 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C15 C7 C33 112.1(3) . . ? C15 C7 C8 109.6(3) . . ? C33 C7 C8 110.0(3) . . ? C15 C7 H7 108.4 . . ? C33 C7 H7 108.4 . . ? C8 C7 H7 108.4 . . ? C7 C8 C13 112.6(3) . . ? C7 C8 C19 111.7(3) . . ? C13 C8 C19 111.2(3) . . ? C7 C8 H8 107 . . ? C13 C8 H8 107 . . ? C19 C8 H8 107 . . ? O3 C11 C3 108.5(3) . . ? O3 C11 C12 106.4(3) . . ? C3 C11 C12 112.5(3) . . ? O3 C11 C24 114.3(3) . . ? C3 C11 C24 111.4(3) . . ? C12 C11 C24 103.7(3) . . ? C17 C12 C15 108.8(3) . . ? C17 C12 C36 109.6(3) . . ? C15 C12 C36 112.2(3) . . ? C17 C12 C11 117.6(3) . . ? C15 C12 C11 99.5(3) . . ? C36 C12 C11 108.9(3) . . ? C17 C13 C8 112.6(3) . . ? C17 C13 H13A 109.1 . . ? C8 C13 H13A 109.1 . . ? C17 C13 H13B 109.1 . . ? C8 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C7 C15 C20 119.6(3) . . ? C7 C15 C12 113.7(3) . . ? C20 C15 C12 102.7(3) . . ? C7 C15 H15 106.7 . . ? C20 C15 H15 106.7 . . ? C12 C15 H15 106.7 . . ? C12 C17 C13 112.1(3) . . ? C12 C17 H17A 109.2 . . ? C13 C17 H17A 109.2 . . ? C12 C17 H17B 109.2 . . ? C13 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C43 C18 C28 122.3(5) . . ? C43 C18 C19 122.5(4) . . ? C28 C18 C19 115.2(3) . . ? C18 C19 C42 111.4(4) . . ? C18 C19 C8 110.7(3) . . ? C42 C19 C8 112.3(3) . . ? C18 C19 H19 107.4 . . ? C42 C19 H19 107.4 . . ? C8 C19 H19 107.4 . . ? C15 C20 C24 105.6(3) . . ? C15 C20 H20A 110.6 . . ? C24 C20 H20A 110.6 . . ? C15 C20 H20B 110.6 . . ? C24 C20 H20B 110.6 . . ? H20A C20 H20B 108.7 . . ? C20 C24 C11 104.9(3) . . ? C20 C24 H24A 110.8 . . ? C11 C24 H24A 110.8 . . ? C20 C24 H24B 110.8 . . ? C11 C24 H24B 110.8 . . ? H24A C24 H24B 108.8 . . ? C18 C28 C33 113.7(4) . . ? C18 C28 H28A 108.8 . . ? C33 C28 H28A 108.8 . . ? C18 C28 H28B 108.8 . . ? C33 C28 H28B 108.8 . . ? H28A C28 H28B 107.7 . . ? C46 C29 C34 118.0(3) . . ? C46 C29 C35 120.9(3) . . ? C34 C29 C35 121.1(3) . . ? C28 C33 C7 111.0(4) . . ? C28 C33 H33A 109.4 . . ? C7 C33 H33A 109.4 . . ? C28 C33 H33B 109.4 . . ? C7 C33 H33B 109.4 . . ? H33A C33 H33B 108 . . ? C46 C34 C29 120.8(3) 2_656 . ? C46 C34 H34 119.6 2_656 . ? C29 C34 H34 119.6 . . ? C3 C35 C29 176.7(4) . . ? C12 C36 H36A 109.5 . . ? C12 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C12 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C54 C42 C19 112.6(4) . . ? C54 C42 H42A 109.1 . . ? C19 C42 H42A 109.1 . . ? C54 C42 H42B 109.1 . . ? C19 C42 H42B 109.1 . . ? H42A C42 H42B 107.8 . . ? C18 C43 C56 123.7(5) . . ? C18 C43 H43 118.1 . . ? C56 C43 H43 118.1 . . ? C29 C46 C34 121.1(4) . 2_656 ? C29 C46 H46 119.4 . . ? C34 C46 H46 119.4 2_656 . ? O6 C48 O3 123.4(4) . . ? O6 C48 C4 126.1(4) . . ? O3 C48 C4 110.5(5) . . ? Cl2 C53 Cl1 112.6(3) . . ? Cl2 C53 Cl3 109.2(3) . . ? Cl1 C53 Cl3 108.8(3) . . ? Cl2 C53 H53 108.7 . . ? Cl1 C53 H53 108.7 . . ? Cl3 C53 H53 108.7 . . ? C56 C54 C42 111.1(4) . . ? C56 C54 H54A 109.4 . . ? C42 C54 H54A 109.4 . . ? C56 C54 H54B 109.4 . . ? C42 C54 H54B 109.4 . . ? H54A C54 H54B 108 . . ? O1 C56 C43 122.4(7) . . ? O1 C56 C54 122.9(6) . . ? C43 C56 C54 114.6(4) . . ? C48 O3 C11 120.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 C7 C8 C13 -52.0(4) . . . . ? C33 C7 C8 C13 -175.6(3) . . . . ? C15 C7 C8 C19 -178.0(3) . . . . ? C33 C7 C8 C19 58.4(4) . . . . ? O3 C11 C12 C17 78.1(4) . . . . ? C3 C11 C12 C17 -40.5(5) . . . . ? C24 C11 C12 C17 -161.0(3) . . . . ? O3 C11 C12 C15 -164.8(3) . . . . ? C3 C11 C12 C15 76.6(4) . . . . ? C24 C11 C12 C15 -43.9(3) . . . . ? O3 C11 C12 C36 -47.3(4) . . . . ? C3 C11 C12 C36 -165.9(3) . . . . ? C24 C11 C12 C36 73.6(4) . . . . ? C7 C8 C13 C17 51.2(4) . . . . ? C19 C8 C13 C17 177.5(3) . . . . ? C33 C7 C15 C20 -59.2(4) . . . . ? C8 C7 C15 C20 178.4(3) . . . . ? C33 C7 C15 C12 179.0(3) . . . . ? C8 C7 C15 C12 56.6(4) . . . . ? C17 C12 C15 C7 -58.5(4) . . . . ? C36 C12 C15 C7 63.0(4) . . . . ? C11 C12 C15 C7 178.0(3) . . . . ? C17 C12 C15 C20 170.8(3) . . . . ? C36 C12 C15 C20 -67.7(4) . . . . ? C11 C12 C15 C20 47.2(3) . . . . ? C15 C12 C17 C13 55.0(4) . . . . ? C36 C12 C17 C13 -68.0(4) . . . . ? C11 C12 C17 C13 167.0(3) . . . . ? C8 C13 C17 C12 -53.3(4) . . . . ? C43 C18 C19 C42 -9.1(6) . . . . ? C28 C18 C19 C42 173.3(4) . . . . ? C43 C18 C19 C8 -134.9(4) . . . . ? C28 C18 C19 C8 47.6(5) . . . . ? C7 C8 C19 C18 -52.6(4) . . . . ? C13 C8 C19 C18 -179.3(3) . . . . ? C7 C8 C19 C42 -177.8(4) . . . . ? C13 C8 C19 C42 55.5(5) . . . . ? C7 C15 C20 C24 -160.1(3) . . . . ? C12 C15 C20 C24 -33.0(4) . . . . ? C15 C20 C24 C11 5.3(4) . . . . ? O3 C11 C24 C20 139.6(3) . . . . ? C3 C11 C24 C20 -97.0(4) . . . . ? C12 C11 C24 C20 24.2(4) . . . . ? C43 C18 C28 C33 134.2(4) . . . . ? C19 C18 C28 C33 -48.2(5) . . . . ? C18 C28 C33 C7 52.4(5) . . . . ? C15 C7 C33 C28 -179.4(3) . . . . ? C8 C7 C33 C28 -57.2(4) . . . . ? C46 C29 C34 C46 -2.1(6) . . . 2_656 ? C35 C29 C34 C46 175.4(4) . . . 2_656 ? C18 C19 C42 C54 40.2(6) . . . . ? C8 C19 C42 C54 165.0(4) . . . . ? C28 C18 C43 C56 172.0(4) . . . . ? C19 C18 C43 C56 -5.4(7) . . . . ? C34 C29 C46 C34 2.0(6) . . . 2_656 ? C35 C29 C46 C34 -175.6(4) . . . 2_656 ? C19 C42 C54 C56 -57.8(6) . . . . ? C18 C43 C56 O1 171.5(5) . . . . ? C18 C43 C56 C54 -12.0(6) . . . . ? C42 C54 C56 O1 -140.6(5) . . . . ? C42 C54 C56 C43 42.9(6) . . . . ? O6 C48 O3 C11 -0.8(7) . . . . ? C4 C48 O3 C11 -179.1(4) . . . . ? C3 C11 O3 C48 -65.7(4) . . . . ? C12 C11 O3 C48 173.1(3) . . . . ? C24 C11 O3 C48 59.2(4) . . . . ? # END of CIF