data_DUTASTERIDE_publ _pd_block_id 2013-12-27T08:43|DUTASTERIDE|James_A._Kaduk|Overall _audit_creation_method "from EXP file using GSAS2CIF" _audit_creation_date 2013-12-27T08:43 _audit_author_name "James A. Kaduk" _audit_update_record ; 2013-12-27T08:43 Initial CIF as created by GSAS2CIF ; #============================================================================= # this information describes the project, paper etc. for the CIF # # Acta Cryst. Section C papers and editorial correspondence is generated # # from the information in this section # # # # (from) CIF submission form for Rietveld refinements (Acta Cryst. C) # # Version 14 December 1998 # #============================================================================= # 1. SUBMISSION DETAILS _publ_contact_author_name 'James A. Kaduk' _publ_contact_author_address # Address of author for correspondence ; ? ; _publ_contact_author_email kaduk@polycrystallography.com _publ_contact_author_fax ? _publ_contact_author_phone 1-630-604-0274 _publ_contact_letter ; ? ; _publ_requested_journal 'Powder Diffraction' _publ_requested_coeditor_name ? _publ_requested_category ? # Acta C: one of CI/CM/CO/FI/FM/FO #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_data_validation_number ? _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_paper_category ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Crystal structure of dutasteride (Avodart), C27 H30 F6 N2 O2 ; _publ_section_title_footnote ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_footnote _publ_author_address ? #<--'Last name, first name' ; ? ; ; ? ; #============================================================================== # 4. TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep # Details of the preparation of the sample(s) # should be given here. ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; ? ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #============================================================================= # 5. OVERALL REFINEMENT & COMPUTING DETAILS _refine_special_details ; ? ; _pd_proc_ls_special_details ; ? ; # The following items are used to identify the programs used. _computing_molecular_graphics ? _computing_publication_material ? _refine_ls_weighting_scheme ? _refine_ls_weighting_details ? _refine_ls_hydrogen_treatment fixed _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_number_constraints ? _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? #============================================================================== # 6. SAMPLE PREPARATION DATA # (In the unusual case where multiple samples are used in a single # Rietveld study, this information should be moved into the phase # blocks) # The following three fields describe the preparation of the material. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature ? _pd_char_colour white data_DUTASTERIDE_overall _refine_ls_shift/su_max 0.01 _refine_ls_shift/su_mean 0.00 _computing_structure_refinement GSAS _refine_ls_number_parameters 104 _refine_ls_goodness_of_fit_all 1.90 _refine_ls_number_restraints 88 _refine_ls_matrix_type full # pointers to the phase blocks loop_ _pd_phase_block_id 2013-12-27T08:43|DUTASTERIDE_phase1|James_A._Kaduk|| # pointers to the diffraction patterns loop_ _pd_block_diffractogram_id ? # Information for phase 1 data_DUTASTERIDE_phase_1 _pd_block_id 2013-12-27T08:43|DUTASTERIDE_phase1|James_A._Kaduk|| #============================================================================== # 7. CHEMICAL, STRUCTURAL AND CRYSTAL DATA _pd_char_particle_morphology ? _chemical_name_systematic ; ? ; _chemical_name_common dutasteride _chemical_formula_moiety 'C27 H30 F6 N2 O2' _chemical_formula_structural 'C27 H30 F6 N2 O2' _chemical_formula_analytical ? _chemical_melting_point ? _chemical_compound_source ? # for minerals and # natural products _symmetry_space_group_name_Hall ? _exptl_crystal_F_000 ? _exptl_crystal_density_diffrn ? _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _cell_measurement_temperature 295 _diffrn_ambient_temperature 295 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.413891 _cell_special_details ; ? ; _geom_special_details ? # The following item identifies the program(s) used (if appropriate). _computing_structure_solution ? #============================================================================== # 8. Phase information from GSAS _pd_phase_name "Dutasteride, C27 H30 F6 N2 O2" _cell_length_a 7.587440(26) _cell_length_b 9.96080(5) _cell_length_c 33.50042(12) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 2531.863(12) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M "P 21 21 21" loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +x,+y,+z 2 +x+1/2,-y+1/2,-z 3 -x,+y+1/2,-z+1/2 4 -x+1/2,-y,+z+1/2 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity C C1 0.8883(9) 0.6482(8) 0.5172(4) 1.0 Uiso 0.0370(10) 4 N N2 0.7255(9) 0.6014(8) 0.51915(28) 1.0 Uiso 0.0370(10) 4 C C3 0.6929(9) 0.4623(8) 0.52810(23) 1.0 Uiso 0.0370(10) 4 C C4 0.8098(10) 0.4188(7) 0.56342(23) 1.0 Uiso 0.0370(10) 4 C C5 0.9972(11) 0.4468(10) 0.55048(32) 1.0 Uiso 0.0370(10) 4 C C6 1.0305(9) 0.5551(10) 0.52867(35) 1.0 Uiso 0.0370(10) 4 O O7 0.9219(8) 0.7704(8) 0.50668(26) 1.0 Uiso 0.0370(10) 4 C C8 0.4984(13) 0.4416(10) 0.53616(30) 1.0 Uiso 0.0370(10) 4 C C9 0.4714(12) 0.2883(11) 0.54189(31) 1.0 Uiso 0.0370(10) 4 C C10 0.5826(10) 0.2353(8) 0.57800(26) 1.0 Uiso 0.0370(10) 4 C C11 0.7762(10) 0.2661(7) 0.57053(26) 1.0 Uiso 0.0370(10) 4 C C12 0.7743(12) 0.4890(12) 0.60313(27) 1.0 Uiso 0.0347(33) 4 C C13 0.5588(10) 0.0812(9) 0.58186(26) 1.0 Uiso 0.0370(10) 4 C C14 0.6639(9) 0.0234(8) 0.61630(25) 1.0 Uiso 0.0370(10) 4 C C15 0.8604(11) 0.0455(9) 0.60694(32) 1.0 Uiso 0.0370(10) 4 C C16 0.8969(11) 0.1973(9) 0.60096(32) 1.0 Uiso 0.0370(10) 4 C C17 0.6126(14) 0.0819(12) 0.65653(30) 1.0 Uiso 0.0347(33) 4 C C18 0.3668(11) 0.0319(11) 0.59093(33) 1.0 Uiso 0.0370(10) 4 C C19 0.4027(12) -0.1143(10) 0.60548(34) 1.0 Uiso 0.0370(10) 4 C C20 0.5998(10) -0.1229(8) 0.61478(25) 1.0 Uiso 0.0370(10) 4 C C21 0.6501(10) -0.2050(10) 0.65049(29) 1.0 Uiso 0.0660(27) 4 O O22 0.8026(10) -0.2076(9) 0.66253(25) 1.0 Uiso 0.0660(27) 4 N N23 0.5279(12) -0.2998(10) 0.66151(29) 1.0 Uiso 0.0660(27) 4 C C24 0.5488(9) -0.4036(6) 0.69086(20) 1.0 Uiso 0.0478(23) 4 C C25 0.4212(7) -0.5033(7) 0.69437(21) 1.0 Uiso 0.0478(23) 4 C C26 0.4438(9) -0.6071(6) 0.72173(22) 1.0 Uiso 0.0478(23) 4 C C27 0.5939(10) -0.6111(7) 0.74558(19) 1.0 Uiso 0.0478(23) 4 C C28 0.7215(7) -0.5114(8) 0.74207(18) 1.0 Uiso 0.0478(23) 4 C C29 0.6989(7) -0.4076(7) 0.71471(20) 1.0 Uiso 0.0478(23) 4 H H30 0.3558(11) -0.6759(7) 0.72415(32) 1.0 Uiso 0.0621(30) 4 H H31 0.6095(14) -0.6827(9) 0.76444(27) 1.0 Uiso 0.0621(30) 4 H H32 0.7869(9) -0.3388(9) 0.71229(30) 1.0 Uiso 0.0621(30) 4 C C33 0.2510(12) -0.4972(10) 0.66812(31) 1.0 Uiso 0.1356(17) 4 F F34 0.1784(11) -0.3875(9) 0.67322(28) 1.0 Uiso 0.1356(17) 4 F F35 0.1434(11) -0.5911(10) 0.67710(25) 1.0 Uiso 0.1356(17) 4 F F36 0.2903(9) -0.5126(10) 0.63189(25) 1.0 Uiso 0.1356(17) 4 C C37 0.8765(11) -0.5190(10) 0.76983(27) 1.0 Uiso 0.1356(17) 4 F F38 0.9204(11) -0.4001(11) 0.78323(28) 1.0 Uiso 0.1356(17) 4 F F39 0.8498(11) -0.5883(10) 0.80071(26) 1.0 Uiso 0.1356(17) 4 F F40 1.0146(12) -0.5557(9) 0.75518(26) 1.0 Uiso 0.1356(17) 4 H H41 0.62197 0.65925 0.51068 1.0 Uiso 0.0482(13) 4 H H42 0.73655 0.40249 0.50534 1.0 Uiso 0.0482(13) 4 H H43 1.10956 0.39696 0.56651 1.0 Uiso 0.0482(13) 4 H H44 1.16629 0.59701 0.52524 1.0 Uiso 0.0482(13) 4 H H45 0.78609 0.59984 0.60026 1.0 Uiso 0.045(4) 4 H H46 0.87200 0.46638 0.62837 1.0 Uiso 0.045(4) 4 H H47 0.64437 0.47044 0.61707 1.0 Uiso 0.045(4) 4 H H48 0.42605 0.47110 0.51145 1.0 Uiso 0.0482(13) 4 H H49 0.44986 0.49043 0.56338 1.0 Uiso 0.0482(13) 4 H H50 0.50479 0.23054 0.51565 1.0 Uiso 0.0482(13) 4 H H51 0.33199 0.26285 0.54917 1.0 Uiso 0.0482(13) 4 H H52 0.53839 0.27553 0.60514 1.0 Uiso 0.0482(13) 4 H H53 0.82226 0.21407 0.54298 1.0 Uiso 0.0482(13) 4 H H54 0.62057 0.03049 0.55488 1.0 Uiso 0.0482(13) 4 H H55 0.90415 -0.01190 0.58340 1.0 Uiso 0.0482(13) 4 H H56 0.94213 0.00602 0.63498 1.0 Uiso 0.0482(13) 4 H H57 0.88127 0.24703 0.63271 1.0 Uiso 0.0482(13) 4 H H58 1.03836 0.20795 0.59674 1.0 Uiso 0.0472(13) 4 H H59 0.62911 0.18238 0.66064 1.0 Uiso 0.045(4) 4 H H60 0.68075 0.02683 0.68238 1.0 Uiso 0.045(4) 4 H H61 0.46642 0.05676 0.66375 1.0 Uiso 0.045(4) 4 H H62 0.30599 0.01409 0.55731 1.0 Uiso 0.0482(13) 4 H H63 0.29563 0.07696 0.60634 1.0 Uiso 0.0482(13) 4 H H64 0.37640 -0.20266 0.58020 1.0 Uiso 0.0482(13) 4 H H65 0.31832 -0.14309 0.62807 1.0 Uiso 0.0482(13) 4 H H66 0.67729 -0.17650 0.58900 1.0 Uiso 0.0482(13) 4 H H67 0.41822 -0.30810 0.64838 1.0 Uiso 0.086(4) 4 loop_ _atom_type_symbol _atom_type_number_in_cell C 108.0 N 8.0 O 8.0 H 120.0 F 24.0 # If you change Z, be sure to change all 3 of the following _chemical_formula_sum "C27 H30 F6 N2 O2" _chemical_formula_weight 528.54 _cell_formula_units_Z 4 # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.322(7) . 1_555 N C1 C6 1.473(8) . 1_555 N C1 O7 1.292(8) . 1_555 N N2 C1 1.322(7) . 1_555 N N2 C3 1.439(8) . 1_555 N N2 H41 1.015(6) . 2_556 N C3 N2 1.439(8) . 1_555 N C3 C4 1.541(5) . 1_555 N C3 C8 1.514(9) . 1_555 N C3 H42 1.023(8) . 2_556 N C4 C3 1.541(5) . 1_555 N C4 C5 1.513(8) . 1_555 N C4 C11 1.561(5) . 1_555 N C4 C12 1.527(5) . 3_656 N C5 C4 1.513(8) . 1_555 N C5 C6 1.327(8) . 1_555 N C5 H43 1.123(8) . 2_556 N C6 C1 1.473(8) . 1_555 N C6 C5 1.327(8) . 1_555 N C6 H44 1.118(7) . 2_556 N O7 C1 1.292(8) . 1_555 N O7 H41 1.770(7) . 1_665 N C8 C3 1.514(9) . 1_555 N C8 C9 1.552(11) . 1_555 N C8 H48 1.036(9) . 2_556 N C8 H49 1.097(10) . 2_556 N C9 C8 1.552(11) . 1_555 N C9 C10 1.566(9) . 1_555 N C9 H50 1.081(11) . 2_556 N C9 H51 1.115(9) . 2_556 N C10 C9 1.566(9) . 1_555 N C10 C11 1.521(7) . 1_555 N C10 C13 1.551(8) . 1_555 N C10 H52 1.049(8) . 2_556 N C11 C4 1.561(5) . 1_555 N C11 C10 1.521(7) . 1_555 N C11 C16 1.532(8) . 1_555 N C11 H53 1.115(9) . 2_556 N C12 C4 1.527(5) . 3_646 N C12 H45 1.112(12) . 4_555 N C12 H46 1.147(10) . 4_555 N C12 H47 1.106(9) . 4_555 N C13 C10 1.551(8) . 1_555 N C13 C14 1.516(8) . 1_555 N C13 C18 1.567(8) . 1_555 N C13 H54 1.137(9) . 2_556 N C14 C13 1.516(8) . 1_555 N C14 C15 1.539(8) . 1_555 N C14 C17 1.519(9) . 3_656 N C14 C20 1.537(8) . 1_555 N C15 C14 1.539(8) . 1_555 N C15 C16 1.550(9) . 1_555 N C15 H55 1.029(10) . 2_556 N C15 H56 1.192(10) . 2_556 N C16 C11 1.532(8) . 1_555 N C16 C15 1.550(9) . 1_555 N C16 H57 1.179(11) . 2_556 N C16 H58 1.088(9) . 2_556 N C17 C14 1.519(9) . 3_646 N C17 H59 1.019(12) . 4_555 N C17 H60 1.148(11) . 4_555 N C17 H61 1.162(10) . 4_555 N C18 C13 1.567(8) . 1_555 N C18 C19 1.560(10) . 1_555 N C18 H62 1.230(11) . 2_556 N C18 H63 0.871(10) . 2_556 N C19 C18 1.560(10) . 1_555 N C19 C20 1.530(8) . 1_555 N C19 H64 1.238(11) . 2_556 N C19 H65 1.032(10) . 2_556 N C20 C14 1.537(8) . 1_555 N C20 C19 1.530(8) . 1_555 N C20 C21 1.499(9) . 1_555 N C20 H66 1.173(8) . 2_556 N C21 C20 1.499(9) . 1_555 N C21 O22 1.225(7) . 1_555 N C21 N23 1.374(8) . 1_555 N O22 C21 1.225(7) . 1_555 N N23 C21 1.374(8) . 1_555 N N23 C24 1.436(7) . 1_555 N N23 H67 0.945(8) . 2_556 N C24 N23 1.436(7) . 1_555 N C24 C25 1.39197 . 1_555 N C24 C29 1.39196 . 1_555 N C25 C24 1.39197 . 1_555 N C25 C26 1.39198 . 1_555 N C25 C33 1.563(8) . 1_555 N C26 C25 1.39198 . 1_555 N C26 C27 1.39198 . 1_555 N C26 H30 0.95992 . 1_555 N C27 C26 1.39198 . 1_555 N C27 C28 1.39197 . 1_555 N C27 H31 0.95979 . 1_555 N C28 C27 1.39197 . 1_555 N C28 C29 1.39201 . 1_555 N C28 C37 1.501(8) . 1_555 N C29 C24 1.39196 . 1_555 N C29 C28 1.39201 . 1_555 N C29 H32 0.95991 . 1_555 N H30 C26 0.95992 . 1_555 N H31 C27 0.95979 . 1_555 N H32 C29 0.95991 . 1_555 N C33 C25 1.563(8) . 1_555 N C33 F34 1.236(12) . 1_555 N C33 F35 1.278(11) . 1_555 N C33 F36 1.259(12) . 1_555 N F34 C33 1.236(12) . 1_555 N F35 C33 1.278(11) . 1_555 N F36 C33 1.259(12) . 1_555 N C37 C28 1.501(8) . 1_555 N C37 F38 1.309(10) . 1_555 N C37 F39 1.260(9) . 1_555 N C37 F40 1.214(9) . 1_555 N F38 C37 1.309(10) . 1_555 N F39 C37 1.260(9) . 1_555 N F40 C37 1.214(9) . 1_555 N H41 N2 1.015(6) . 2_456 N H41 O7 1.770(7) . 1_445 N H42 C3 1.023(8) . 2_456 N H43 C5 1.123(8) . 2_456 N H44 C6 1.118(7) . 2_456 N H45 C12 1.112(12) . 4_554 N H46 C12 1.147(10) . 4_554 N H47 C12 1.106(9) . 4_554 N H48 C8 1.036(9) . 2_456 N H49 C8 1.097(10) . 2_456 N H50 C9 1.081(11) . 2_456 N H51 C9 1.115(9) . 2_456 N H52 C10 1.049(8) . 2_456 N H53 C11 1.115(9) . 2_456 N H54 C13 1.137(9) . 2_456 N H55 C15 1.029(10) . 2_456 N H56 C15 1.192(10) . 2_456 N H57 C16 1.179(11) . 2_456 N H58 C16 1.088(9) . 2_456 N H59 C17 1.019(12) . 4_554 N H60 C17 1.148(11) . 4_554 N H61 C17 1.162(10) . 4_554 N H62 C18 1.230(11) . 2_456 N H63 C18 0.871(10) . 2_456 N H64 C19 1.238(11) . 2_456 N H65 C19 1.032(10) . 2_456 N H66 C20 1.173(8) . 2_456 N H67 N23 0.945(8) . 2_456 N 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C6 116.7(4) 1_555 . 1_555 N N2 C1 O7 122.0(5) 1_555 . 1_555 N C6 C1 O7 121.3(6) 1_555 . 1_555 N C1 N2 C3 120.7(4) 1_555 . 1_555 N C1 N2 H41 120.6(6) 1_555 . 2_556 N C3 N2 H41 118.2(7) 1_555 . 2_556 N N2 C3 C4 109.4(5) 1_555 . 1_555 N N2 C3 C8 109.6(5) 1_555 . 1_555 N N2 C3 H42 110.5(7) 1_555 . 2_556 N C4 C3 C8 112.7(5) 1_555 . 1_555 N C4 C3 H42 102.8(6) 1_555 . 2_556 N C8 C3 H42 111.7(6) 1_555 . 2_556 N C3 C4 C5 105.6(4) 1_555 . 1_555 N C3 C4 C11 107.3(5) 1_555 . 1_555 N C3 C4 C12 116.0(7) 1_555 . 3_656 N C5 C4 C11 112.2(5) 1_555 . 1_555 N C5 C4 C12 109.3(8) 1_555 . 3_656 N C11 C4 C12 106.5(7) 1_555 . 3_656 N C4 C5 C6 119.1(6) 1_555 . 1_555 N C4 C5 H43 119.6(7) 1_555 . 2_556 N C6 C5 H43 118.6(8) 1_555 . 2_556 N C1 C6 C5 121.1(5) 1_555 . 1_555 N C1 C6 H44 114.4(7) 1_555 . 2_556 N C5 C6 H44 122.4(9) 1_555 . 2_556 N C3 C8 C9 106.6(6) 1_555 . 1_555 N C3 C8 H48 109.6(8) 1_555 . 2_556 N C3 C8 H49 114.5(8) 1_555 . 2_556 N C9 C8 H48 107.9(9) 1_555 . 2_556 N C9 C8 H49 106.8(8) 1_555 . 2_556 N H48 C8 H49 111.1(8) 2_556 . 2_556 N C8 C9 C10 110.9(7) 1_555 . 1_555 N C8 C9 H50 113.1(9) 1_555 . 2_556 N C8 C9 H51 112.1(9) 1_555 . 2_556 N C10 C9 H50 108.8(9) 1_555 . 2_556 N C10 C9 H51 105.4(8) 1_555 . 2_556 N H50 C9 H51 106.2(8) 2_556 . 2_556 N C9 C10 C11 109.0(5) 1_555 . 1_555 N C9 C10 C13 109.6(7) 1_555 . 1_555 N C9 C10 H52 111.6(7) 1_555 . 2_556 N C11 C10 C13 109.0(4) 1_555 . 1_555 N C11 C10 H52 112.0(7) 1_555 . 2_556 N C13 C10 H52 105.6(7) 1_555 . 2_556 N C4 C11 C10 112.3(4) 1_555 . 1_555 N C4 C11 C16 116.1(5) 1_555 . 1_555 N C4 C11 H53 106.0(6) 1_555 . 2_556 N C10 C11 C16 112.2(5) 1_555 . 1_555 N C10 C11 H53 110.2(6) 1_555 . 2_556 N C16 C11 H53 99.0(7) 1_555 . 2_556 N C4 C12 H45 111.4(8) 3_646 . 4_555 N C4 C12 H46 116.0(9) 3_646 . 4_555 N C4 C12 H47 116.6(8) 3_646 . 4_555 N H45 C12 H46 101.9(7) 4_555 . 4_555 N H45 C12 H47 105.9(9) 4_555 . 4_555 N H46 C12 H47 103.4(8) 4_555 . 4_555 N C10 C13 C14 112.2(6) 1_555 . 1_555 N C10 C13 C18 115.7(6) 1_555 . 1_555 N C10 C13 H54 109.0(6) 1_555 . 2_556 N C14 C13 C18 102.9(5) 1_555 . 1_555 N C14 C13 H54 102.7(7) 1_555 . 2_556 N C18 C13 H54 113.5(8) 1_555 . 2_556 N C13 C14 C15 107.5(6) 1_555 . 1_555 N C13 C14 C17 113.3(7) 1_555 . 3_656 N C13 C14 C20 99.7(4) 1_555 . 1_555 N C15 C14 C17 112.0(7) 1_555 . 3_656 N C15 C14 C20 115.8(5) 1_555 . 1_555 N C17 C14 C20 108.2(7) 3_656 . 1_555 N C14 C15 C16 109.8(6) 1_555 . 1_555 N C14 C15 H55 112.9(8) 1_555 . 2_556 N C14 C15 H56 107.2(8) 1_555 . 2_556 N C16 C15 H55 112.7(9) 1_555 . 2_556 N C16 C15 H56 109.3(8) 1_555 . 2_556 N H55 C15 H56 104.6(7) 2_556 . 2_556 N C11 C16 C15 114.5(6) 1_555 . 1_555 N C11 C16 H57 110.6(8) 1_555 . 2_556 N C11 C16 H58 117.4(8) 1_555 . 2_556 N C15 C16 H57 106.0(8) 1_555 . 2_556 N C15 C16 H58 106.8(8) 1_555 . 2_556 N H57 C16 H58 100.1(7) 2_556 . 2_556 N C14 C17 H59 117.7(9) 3_646 . 4_555 N C14 C17 H60 111.8(9) 3_646 . 4_555 N C14 C17 H61 110.3(8) 3_646 . 4_555 N H59 C17 H60 108.2(9) 4_555 . 4_555 N H59 C17 H61 107.5(9) 4_555 . 4_555 N H60 C17 H61 99.8(8) 4_555 . 4_555 N C13 C18 C19 101.0(6) 1_555 . 1_555 N C13 C18 H62 102.5(8) 1_555 . 2_556 N C13 C18 H63 122.0(11) 1_555 . 2_556 N C19 C18 H62 102.5(9) 1_555 . 2_556 N C19 C18 H63 113.8(11) 1_555 . 2_556 N H62 C18 H63 112.6(8) 2_556 . 2_556 N C18 C19 C20 106.7(6) 1_555 . 1_555 N C18 C19 H64 114.9(9) 1_555 . 2_556 N C18 C19 H65 112.3(10) 1_555 . 2_556 N C20 C19 H64 104.9(8) 1_555 . 2_556 N C20 C19 H65 116.2(9) 1_555 . 2_556 N H64 C19 H65 101.8(7) 2_556 . 2_556 N C14 C20 C19 105.2(5) 1_555 . 1_555 N C14 C20 C21 114.2(5) 1_555 . 1_555 N C14 C20 H66 107.3(6) 1_555 . 2_556 N C19 C20 C21 116.2(7) 1_555 . 1_555 N C19 C20 H66 111.4(8) 1_555 . 2_556 N C21 C20 H66 102.2(7) 1_555 . 2_556 N C20 C21 O22 121.0(5) 1_555 . 1_555 N C20 C21 N23 114.7(5) 1_555 . 1_555 N O22 C21 N23 122.3(7) 1_555 . 1_555 N C21 N23 C24 127.2(6) 1_555 . 1_555 N C21 N23 H67 122.0(7) 1_555 . 2_556 N C24 N23 H67 110.7(7) 1_555 . 2_556 N N23 C24 C25 119.7(4) 1_555 . 1_555 N N23 C24 C29 120.3(4) 1_555 . 1_555 N C25 C24 C29 119.99900(10) 1_555 . 1_555 N C24 C25 C26 120.00080(20) 1_555 . 1_555 N C24 C25 C33 119.9(4) 1_555 . 1_555 N C26 C25 C33 120.1(4) 1_555 . 1_555 N C25 C26 C27 120.00070(10) 1_555 . 1_555 N C25 C26 H30 120.00200(20) 1_555 . 1_555 N C27 C26 H30 119.99730(10) 1_555 . 1_555 N C26 C27 C28 119.99850(20) 1_555 . 1_555 N C26 C27 H31 120.0007 1_555 . 1_555 N C28 C27 H31 120.0008 1_555 . 1_555 N C27 C28 C29 120.00010(20) 1_555 . 1_555 N C27 C28 C37 117.2(6) 1_555 . 1_555 N C29 C28 C37 122.8(6) 1_555 . 1_555 N C24 C29 C28 120.00090(10) 1_555 . 1_555 N C24 C29 H32 119.9992 1_555 . 1_555 N C28 C29 H32 119.99990(10) 1_555 . 1_555 N C25 C33 F34 109.0(8) 1_555 . 1_555 N C25 C33 F35 111.5(7) 1_555 . 1_555 N C25 C33 F36 110.0(7) 1_555 . 1_555 N F34 C33 F35 109.3(9) 1_555 . 1_555 N F34 C33 F36 110.3(10) 1_555 . 1_555 N F35 C33 F36 106.8(9) 1_555 . 1_555 N C28 C37 F38 111.5(7) 1_555 . 1_555 N C28 C37 F39 114.2(7) 1_555 . 1_555 N C28 C37 F40 116.2(7) 1_555 . 1_555 N F38 C37 F39 104.8(6) 1_555 . 1_555 N F38 C37 F40 101.1(6) 1_555 . 1_555 N F39 C37 F40 107.8(7) 1_555 . 1_555 N #--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--#