#------------------------------------------------------------------------------ #$Date: 2015-09-26 10:42:15 +0300 (Sat, 26 Sep 2015) $ #$Revision: 158423 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/23/7222303.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7222303 loop_ _publ_author_name 'Kwit, Marcin' 'Rychlewska, Urszula' 'Prusinowska, Natalia' 'Bendzi\'nska-Berus, Wioletta' 'War\.zajtis, Beata' 'Gajewy, Jadwiga' 'Szymkowiak, Joanna' 'Jelecki, Maciej' _publ_section_title ; Double helicity induction in chiral bis(triphenylacetamides) ; _journal_name_full 'RSC Adv.' _journal_paper_doi 10.1039/C5RA15554A _journal_year 2015 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C46 H42 N2 O2, C H2 Cl2' _chemical_formula_sum 'C47 H44 Cl2 N2 O2' _chemical_formula_weight 739.74 _chemical_name_systematic ; ? ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _audit_update_record ; 2015-07-23 deposited with the CCDC. 2015-09-25 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 94.859(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.0299(2) _cell_length_b 10.5552(2) _cell_length_c 20.7459(3) _cell_measurement_reflns_used 18235 _cell_measurement_temperature 130(2) _cell_measurement_theta_max 76.2945 _cell_measurement_theta_min 4.1849 _cell_volume 1970.24(6) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies (2013) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies (2013) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies (2013) ; _computing_molecular_graphics ; Mercury (Bruno, et al. 2002) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 2008)' _diffrn_ambient_temperature 130(2) _diffrn_detector_area_resol_mean 10.5357 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'SuperNova, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0129 _diffrn_reflns_av_sigmaI/netI 0.0129 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 20573 _diffrn_reflns_theta_full 66.57 _diffrn_reflns_theta_max 66.57 _diffrn_reflns_theta_min 4.70 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 50 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 1.796 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.79067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro (Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm, Agilent Technologies 2013) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 780 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.453 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.017(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 478 _refine_ls_number_reflns 6844 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0364 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.5716P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1070 _refine_ls_wR_factor_ref 0.1073 _reflns_number_gt 6790 _reflns_number_total 6844 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL chnhchcl in P2(1) CELL 1.54178 9.0299 10.5552 20.7459 90.000 94.859 90.000 ZERR 2.00 0.0002 0.0002 0.0003 0.000 0.002 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O CL UNIT 94 88 4 4 4 MERG 2 OMIT 0 0 6 DELU 0.006 C5 C6 SHEL 10.0 0.84 FMAP 2 PLAN 10 SIZE 0.080 0.200 0.350 ACTA BOND $H CONF L.S. 10 TEMP -143.00 WGHT 0.069000 0.571600 FVAR 6.93705 C3 1 0.463977 0.556119 0.844738 11.00000 0.03830 0.02559 = 0.02759 0.00008 0.00793 0.00014 AFIX 13 H3 2 0.364539 0.519717 0.852054 11.00000 -1.20000 AFIX 0 C1S 1 0.076927 0.403822 0.862284 11.00000 0.04190 0.05781 = 0.04145 -0.00770 0.00361 -0.00515 AFIX 23 H1S1 2 0.126306 0.412622 0.821695 11.00000 -1.20000 H1S2 2 -0.017631 0.357623 0.852243 11.00000 -1.20000 AFIX 0 C8 1 0.584714 0.459327 0.866235 11.00000 0.03966 0.02419 = 0.03905 -0.00103 -0.00797 -0.00652 AFIX 13 H8 2 0.681566 0.490781 0.852399 11.00000 -1.20000 AFIX 0 C7 1 0.601226 0.441090 0.938750 11.00000 0.07510 0.05543 = 0.04236 0.01478 -0.02039 -0.02674 AFIX 23 H7B 2 0.509556 0.401728 0.952560 11.00000 -1.20000 H7A 2 0.684755 0.382282 0.950175 11.00000 -1.20000 AFIX 0 C6 1 0.629384 0.563857 0.974829 11.00000 0.09990 0.08012 = 0.03024 -0.00833 -0.00353 -0.03661 AFIX 23 H6B 2 0.636933 0.547901 1.022018 11.00000 -1.20000 H6A 2 0.724289 0.601374 0.963539 11.00000 -1.20000 AFIX 0 C5 1 0.504519 0.653291 0.957037 11.00000 0.09984 0.06961 = 0.05215 -0.04013 0.03668 -0.03619 AFIX 23 H5A 2 0.523385 0.734200 0.980441 11.00000 -1.20000 H5B 2 0.411050 0.617079 0.970752 11.00000 -1.20000 AFIX 0 C4 1 0.485960 0.679587 0.883330 11.00000 0.06239 0.02661 = 0.05937 -0.01230 0.02206 -0.00661 AFIX 23 H4B 2 0.399086 0.735558 0.873292 11.00000 -1.20000 H4A 2 0.575258 0.723996 0.870288 11.00000 -1.20000 AFIX 0 C1 1 0.368533 0.542356 0.729380 11.00000 0.03071 0.02352 = 0.02856 0.00147 0.00767 0.00268 C2 1 0.649570 0.269349 0.806159 11.00000 0.02864 0.02934 = 0.02841 0.00504 -0.00251 -0.00458 C10 1 0.404692 0.572346 0.658071 11.00000 0.02803 0.02549 = 0.02772 0.00243 0.00808 0.00083 C21 1 0.574077 0.591910 0.657173 11.00000 0.02874 0.02994 = 0.02766 0.00374 0.00769 0.00322 C26 1 0.635362 0.708755 0.643236 11.00000 0.03197 0.02805 = 0.03484 0.00353 0.00462 0.00259 AFIX 43 H26 2 0.571864 0.777118 0.629550 11.00000 -1.20000 AFIX 0 C25 1 0.788323 0.726477 0.649122 11.00000 0.03526 0.03400 = 0.05227 0.00426 0.00807 -0.00437 AFIX 43 H25 2 0.828221 0.806588 0.638924 11.00000 -1.20000 AFIX 0 C24 1 0.882614 0.629768 0.669480 11.00000 0.02795 0.04481 = 0.06423 0.00483 0.01153 -0.00028 AFIX 43 H24 2 0.986975 0.643277 0.674400 11.00000 -1.20000 AFIX 0 C23 1 0.823735 0.511731 0.682837 11.00000 0.03243 0.04161 = 0.06164 0.01325 0.01175 0.01069 AFIX 43 H23 2 0.887953 0.443592 0.696130 11.00000 -1.20000 AFIX 0 C22 1 0.671296 0.493899 0.676694 11.00000 0.03152 0.03358 = 0.04671 0.01106 0.01141 0.00387 AFIX 43 H22 2 0.632032 0.413062 0.685988 11.00000 -1.20000 AFIX 0 C31 1 0.344759 0.462723 0.613349 11.00000 0.03477 0.02667 = 0.02723 0.00260 0.00874 0.00047 C36 1 0.433168 0.393718 0.574352 11.00000 0.04218 0.03388 = 0.04016 -0.00256 0.01310 0.00416 AFIX 43 H36 2 0.536820 0.410261 0.575884 11.00000 -1.20000 AFIX 0 C35 1 0.370753 0.300549 0.533083 11.00000 0.06707 0.03648 = 0.04451 -0.00767 0.01657 0.00815 AFIX 43 H35 2 0.433152 0.253051 0.507446 11.00000 -1.20000 AFIX 0 C34 1 0.221426 0.275819 0.528608 11.00000 0.06970 0.02924 = 0.03800 -0.00211 0.00520 -0.01005 AFIX 43 H34 2 0.180015 0.212495 0.499945 11.00000 -1.20000 AFIX 0 C33 1 0.131987 0.344873 0.566656 11.00000 0.04570 0.04578 = 0.03889 0.00136 0.00529 -0.01187 AFIX 43 H33 2 0.028191 0.328654 0.564374 11.00000 -1.20000 AFIX 0 C32 1 0.192854 0.437165 0.607890 11.00000 0.03615 0.04648 = 0.03364 -0.00575 0.00818 -0.00220 AFIX 43 H32 2 0.129582 0.484488 0.633202 11.00000 -1.20000 AFIX 0 C11 1 0.318763 0.693364 0.636110 11.00000 0.02293 0.02739 = 0.03299 0.00118 0.00412 -0.00004 C16 1 0.305890 0.723104 0.570216 11.00000 0.03241 0.03497 = 0.03129 0.00057 0.00422 0.00337 AFIX 43 H16 2 0.348832 0.668102 0.540703 11.00000 -1.20000 AFIX 0 C15 1 0.232385 0.830314 0.547080 11.00000 0.03575 0.04010 = 0.03796 0.00768 -0.00132 0.00367 AFIX 43 H15 2 0.226085 0.848914 0.502128 11.00000 -1.20000 AFIX 0 C14 1 0.167518 0.911209 0.589284 11.00000 0.03500 0.03052 = 0.05507 0.00569 -0.00282 0.00735 AFIX 43 H14 2 0.115708 0.984692 0.573437 11.00000 -1.20000 AFIX 0 C13 1 0.179150 0.883667 0.654541 11.00000 0.03513 0.02979 = 0.05088 -0.00552 0.00653 0.00574 AFIX 43 H13 2 0.134989 0.938549 0.683741 11.00000 -1.20000 AFIX 0 C12 1 0.255063 0.776123 0.677925 11.00000 0.03041 0.03073 = 0.03331 -0.00250 0.00401 -0.00019 AFIX 43 H12 2 0.263433 0.759083 0.723051 11.00000 -1.20000 AFIX 0 C20 1 0.601526 0.134628 0.779488 11.00000 0.02553 0.02322 = 0.03262 0.00381 0.00198 -0.00143 C61 1 0.434660 0.112282 0.785161 11.00000 0.02655 0.02141 = 0.03402 -0.00357 0.00462 -0.00207 C66 1 0.382746 0.020483 0.826345 11.00000 0.03208 0.02575 = 0.03636 -0.00002 0.00501 -0.00118 AFIX 43 H66 2 0.451454 -0.032735 0.850691 11.00000 -1.20000 AFIX 0 C65 1 0.231040 0.006606 0.831885 11.00000 0.03454 0.03390 = 0.04263 -0.00215 0.01336 -0.00910 AFIX 43 H65 2 0.197326 -0.056459 0.859859 11.00000 -1.20000 AFIX 0 C64 1 0.128997 0.083049 0.797368 11.00000 0.02653 0.04162 = 0.04630 -0.01130 0.00891 -0.00529 AFIX 43 H64 2 0.025765 0.073558 0.801875 11.00000 -1.20000 AFIX 0 C63 1 0.178715 0.174025 0.755963 11.00000 0.02766 0.03104 = 0.04483 -0.00780 -0.00135 -0.00060 AFIX 43 H63 2 0.109228 0.226797 0.731771 11.00000 -1.20000 AFIX 0 C62 1 0.329533 0.188065 0.749826 11.00000 0.02767 0.02374 = 0.04176 -0.00152 0.00107 -0.00142 AFIX 43 H62 2 0.362157 0.250267 0.721110 11.00000 -1.20000 AFIX 0 C51 1 0.640476 0.121265 0.708340 11.00000 0.02933 0.02071 = 0.03529 0.00551 0.00384 0.00129 C56 1 0.543877 0.064412 0.660733 11.00000 0.03017 0.03345 = 0.03566 0.00510 0.00223 -0.00107 AFIX 43 H56 2 0.445590 0.043935 0.670198 11.00000 -1.20000 AFIX 0 C55 1 0.588415 0.037358 0.600142 11.00000 0.04128 0.03884 = 0.03392 0.00295 -0.00054 0.00167 AFIX 43 H55 2 0.520266 -0.000929 0.568580 11.00000 -1.20000 AFIX 0 C54 1 0.730592 0.065227 0.584882 11.00000 0.04783 0.03319 = 0.03734 0.00810 0.01107 0.00725 AFIX 43 H54 2 0.761595 0.044892 0.543492 11.00000 -1.20000 AFIX 0 C53 1 0.827211 0.123490 0.631182 11.00000 0.03847 0.03513 = 0.05133 0.00485 0.01776 0.00075 AFIX 43 H53 2 0.924777 0.144915 0.621082 11.00000 -1.20000 AFIX 0 C52 1 0.783329 0.150818 0.691902 11.00000 0.03191 0.02943 = 0.04565 0.00009 0.00753 -0.00236 AFIX 43 H52 2 0.851519 0.190391 0.722997 11.00000 -1.20000 AFIX 0 C41 1 0.697728 0.039481 0.821188 11.00000 0.02456 0.03195 = 0.03961 0.01158 0.00560 0.00046 C46 1 0.744227 -0.073532 0.794843 11.00000 0.03420 0.03086 = 0.04643 0.00877 -0.00143 -0.00231 AFIX 43 H46 2 0.716792 -0.092459 0.750673 11.00000 -1.20000 AFIX 0 C45 1 0.830932 -0.159320 0.832866 11.00000 0.04080 0.03381 = 0.06023 0.01372 0.00340 0.00515 AFIX 43 H45 2 0.862704 -0.235985 0.814401 11.00000 -1.20000 AFIX 0 C44 1 0.870679 -0.132992 0.897330 11.00000 0.04421 0.04865 = 0.05697 0.02533 -0.00213 0.00962 AFIX 43 H44 2 0.930176 -0.191048 0.923158 11.00000 -1.20000 AFIX 0 C43 1 0.823531 -0.022401 0.923686 11.00000 0.06569 0.06352 = 0.03857 0.01464 -0.00317 0.01409 AFIX 43 H43 2 0.849932 -0.004265 0.968026 11.00000 -1.20000 AFIX 0 C42 1 0.737563 0.063141 0.886040 11.00000 0.05171 0.05069 = 0.03854 0.01092 0.00651 0.01243 AFIX 43 H42 2 0.705493 0.139168 0.905037 11.00000 -1.20000 AFIX 0 N1 3 0.469073 0.582552 0.776206 11.00000 0.02904 0.04863 = 0.02952 0.00752 0.00540 -0.00486 AFIX 43 H1 2 0.543738 0.628372 0.764564 11.00000 -1.20000 AFIX 0 N2 3 0.550388 0.338516 0.833693 11.00000 0.02787 0.02593 = 0.06154 -0.00769 -0.00213 -0.00439 AFIX 43 H2 2 0.458476 0.310305 0.832380 11.00000 -1.20000 AFIX 0 O1 4 0.254457 0.489672 0.741231 11.00000 0.04489 0.05312 = 0.03159 -0.00361 0.01120 -0.01985 O2 4 0.777268 0.304856 0.804078 11.00000 0.03896 0.05810 = 0.05221 -0.02005 0.01168 -0.02209 CL1 5 0.193653 0.315483 0.919650 11.00000 0.07276 0.04762 = 0.04430 -0.00136 -0.00554 0.00587 CL2 5 0.039475 0.554553 0.892476 11.00000 0.09792 0.07284 = 0.07028 -0.01193 -0.00736 0.04303 HKLF 4 REM chnhchcl in P2(1) REM R1 = 0.0364 for 6790 Fo > 4sig(Fo) and 0.0366 for all 6844 data REM 478 parameters refined using 2 restraints END WGHT 0.0690 0.5716 REM Highest difference peak 0.453, deepest hole -0.400, 1-sigma level 0.042 Q1 1 0.0313 0.4826 0.8374 11.00000 0.05 0.45 Q2 1 0.4025 0.6823 0.9401 11.00000 0.05 0.31 Q3 1 0.0786 0.3157 0.9202 11.00000 0.05 0.26 Q4 1 0.5399 0.4933 0.9571 11.00000 0.05 0.25 Q5 1 0.3943 0.5652 0.6880 11.00000 0.05 0.21 Q6 1 0.5112 0.1281 0.7817 11.00000 0.05 0.20 Q7 1 0.3762 0.5159 0.6370 11.00000 0.05 0.20 Q8 1 0.6230 0.5537 0.6767 11.00000 0.05 0.19 Q9 1 0.5997 0.6385 0.6317 11.00000 0.05 0.18 Q10 1 0.4023 0.1406 0.7727 11.00000 0.05 0.18 ; _cod_data_source_file c5ra15554a2.cif _cod_data_source_block 4a _cod_cif_authors_sg_H-M P21 _cod_database_code 7222303 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 C3 C 0.4640(2) 0.55612(19) 0.84474(9) 0.0302(4) Uani 1 1 d . H3 H 0.3645 0.5197 0.8521 0.036 Uiso 1 1 calc R C1S C 0.0769(3) 0.4038(3) 0.86228(12) 0.0471(6) Uani 1 1 d . H1S1 H 0.1263 0.4126 0.8217 0.056 Uiso 1 1 calc R H1S2 H -0.0176 0.3576 0.8522 0.056 Uiso 1 1 calc R C8 C 0.5847(2) 0.4593(2) 0.86623(10) 0.0349(4) Uani 1 1 d . H8 H 0.6816 0.4908 0.8524 0.042 Uiso 1 1 calc R C7 C 0.6012(4) 0.4411(3) 0.93875(13) 0.0591(8) Uani 1 1 d . H7B H 0.5096 0.4017 0.9526 0.071 Uiso 1 1 calc R H7A H 0.6848 0.3823 0.9502 0.071 Uiso 1 1 calc R C6 C 0.6294(4) 0.5639(4) 0.97483(13) 0.0706(9) Uani 1 1 d U H6B H 0.6369 0.5479 1.0220 0.085 Uiso 1 1 calc R H6A H 0.7243 0.6014 0.9635 0.085 Uiso 1 1 calc R C5 C 0.5045(4) 0.6533(3) 0.95704(14) 0.0721(9) Uani 1 1 d U H5A H 0.5234 0.7342 0.9804 0.087 Uiso 1 1 calc R H5B H 0.4111 0.6171 0.9708 0.087 Uiso 1 1 calc R C4 C 0.4860(3) 0.6796(2) 0.88333(13) 0.0485(6) Uani 1 1 d . H4B H 0.3991 0.7356 0.8733 0.058 Uiso 1 1 calc R H4A H 0.5753 0.7240 0.8703 0.058 Uiso 1 1 calc R C1 C 0.3685(2) 0.54236(18) 0.72938(9) 0.0273(4) Uani 1 1 d . C2 C 0.6496(2) 0.26935(19) 0.80616(9) 0.0291(4) Uani 1 1 d . C10 C 0.4047(2) 0.57235(18) 0.65807(9) 0.0268(4) Uani 1 1 d . C21 C 0.5741(2) 0.59191(19) 0.65717(9) 0.0285(4) Uani 1 1 d . C26 C 0.6354(2) 0.7088(2) 0.64324(10) 0.0315(4) Uani 1 1 d . H26 H 0.5719 0.7771 0.6295 0.038 Uiso 1 1 calc R C25 C 0.7883(2) 0.7265(2) 0.64912(12) 0.0403(5) Uani 1 1 d . H25 H 0.8282 0.8066 0.6389 0.048 Uiso 1 1 calc R C24 C 0.8826(2) 0.6298(2) 0.66948(13) 0.0452(5) Uani 1 1 d . H24 H 0.9870 0.6433 0.6744 0.054 Uiso 1 1 calc R C23 C 0.8237(2) 0.5117(2) 0.68284(13) 0.0448(6) Uani 1 1 d . H23 H 0.8880 0.4436 0.6961 0.054 Uiso 1 1 calc R C22 C 0.6713(2) 0.4939(2) 0.67669(11) 0.0368(5) Uani 1 1 d . H22 H 0.6320 0.4131 0.6860 0.044 Uiso 1 1 calc R C31 C 0.3448(2) 0.46272(19) 0.61335(9) 0.0292(4) Uani 1 1 d . C36 C 0.4332(3) 0.3937(2) 0.57435(11) 0.0382(5) Uani 1 1 d . H36 H 0.5368 0.4103 0.5759 0.046 Uiso 1 1 calc R C35 C 0.3708(3) 0.3005(2) 0.53308(12) 0.0487(6) Uani 1 1 d . H35 H 0.4332 0.2531 0.5074 0.058 Uiso 1 1 calc R C34 C 0.2214(3) 0.2758(2) 0.52861(11) 0.0456(6) Uani 1 1 d . H34 H 0.1800 0.2125 0.4999 0.055 Uiso 1 1 calc R C33 C 0.1320(3) 0.3449(2) 0.56666(11) 0.0434(5) Uani 1 1 d . H33 H 0.0282 0.3287 0.5644 0.052 Uiso 1 1 calc R C32 C 0.1929(2) 0.4372(2) 0.60789(10) 0.0385(5) Uani 1 1 d . H32 H 0.1296 0.4845 0.6332 0.046 Uiso 1 1 calc R C11 C 0.3188(2) 0.69336(19) 0.63611(9) 0.0277(4) Uani 1 1 d . C16 C 0.3059(2) 0.7231(2) 0.57022(10) 0.0328(4) Uani 1 1 d . H16 H 0.3488 0.6681 0.5407 0.039 Uiso 1 1 calc R C15 C 0.2324(2) 0.8303(2) 0.54708(10) 0.0382(5) Uani 1 1 d . H15 H 0.2261 0.8489 0.5021 0.046 Uiso 1 1 calc R C14 C 0.1675(2) 0.9112(2) 0.58928(12) 0.0406(5) Uani 1 1 d . H14 H 0.1157 0.9847 0.5734 0.049 Uiso 1 1 calc R C13 C 0.1791(2) 0.8837(2) 0.65454(11) 0.0384(5) Uani 1 1 d . H13 H 0.1350 0.9385 0.6837 0.046 Uiso 1 1 calc R C12 C 0.2551(2) 0.7761(2) 0.67793(10) 0.0314(4) Uani 1 1 d . H12 H 0.2634 0.7591 0.7231 0.038 Uiso 1 1 calc R C20 C 0.6015(2) 0.13463(18) 0.77949(9) 0.0272(4) Uani 1 1 d . C61 C 0.4347(2) 0.11228(18) 0.78516(9) 0.0272(4) Uani 1 1 d . C66 C 0.3827(2) 0.02048(19) 0.82634(10) 0.0313(4) Uani 1 1 d . H66 H 0.4515 -0.0327 0.8507 0.038 Uiso 1 1 calc R C65 C 0.2310(2) 0.0066(2) 0.83189(11) 0.0364(5) Uani 1 1 d . H65 H 0.1973 -0.0565 0.8599 0.044 Uiso 1 1 calc R C64 C 0.1290(2) 0.0830(2) 0.79737(11) 0.0378(5) Uani 1 1 d . H64 H 0.0258 0.0736 0.8019 0.045 Uiso 1 1 calc R C63 C 0.1787(2) 0.1740(2) 0.75596(11) 0.0348(4) Uani 1 1 d . H63 H 0.1092 0.2268 0.7318 0.042 Uiso 1 1 calc R C62 C 0.3295(2) 0.18806(19) 0.74983(10) 0.0312(4) Uani 1 1 d . H62 H 0.3622 0.2503 0.7211 0.037 Uiso 1 1 calc R C51 C 0.6405(2) 0.12127(18) 0.70834(10) 0.0284(4) Uani 1 1 d . C56 C 0.5439(2) 0.0644(2) 0.66073(10) 0.0331(4) Uani 1 1 d . H56 H 0.4456 0.0439 0.6702 0.040 Uiso 1 1 calc R C55 C 0.5884(2) 0.0374(2) 0.60014(10) 0.0382(5) Uani 1 1 d . H55 H 0.5203 -0.0009 0.5686 0.046 Uiso 1 1 calc R C54 C 0.7306(3) 0.0652(2) 0.58488(11) 0.0390(5) Uani 1 1 d . H54 H 0.7616 0.0449 0.5435 0.047 Uiso 1 1 calc R C53 C 0.8272(3) 0.1235(2) 0.63118(12) 0.0408(5) Uani 1 1 d . H53 H 0.9248 0.1449 0.6211 0.049 Uiso 1 1 calc R C52 C 0.7833(2) 0.1508(2) 0.69190(11) 0.0354(4) Uani 1 1 d . H52 H 0.8515 0.1904 0.7230 0.043 Uiso 1 1 calc R C41 C 0.6977(2) 0.0395(2) 0.82119(10) 0.0319(4) Uani 1 1 d . C46 C 0.7442(2) -0.0735(2) 0.79484(11) 0.0374(5) Uani 1 1 d . H46 H 0.7168 -0.0925 0.7507 0.045 Uiso 1 1 calc R C45 C 0.8309(3) -0.1593(2) 0.83287(13) 0.0450(5) Uani 1 1 d . H45 H 0.8627 -0.2360 0.8144 0.054 Uiso 1 1 calc R C44 C 0.8707(3) -0.1330(3) 0.89733(13) 0.0503(6) Uani 1 1 d . H44 H 0.9302 -0.1910 0.9232 0.060 Uiso 1 1 calc R C43 C 0.8235(3) -0.0224(3) 0.92369(13) 0.0564(7) Uani 1 1 d . H43 H 0.8499 -0.0043 0.9680 0.068 Uiso 1 1 calc R C42 C 0.7376(3) 0.0631(3) 0.88604(11) 0.0468(5) Uani 1 1 d . H42 H 0.7055 0.1392 0.9050 0.056 Uiso 1 1 calc R N1 N 0.46907(18) 0.58255(19) 0.77621(8) 0.0356(4) Uani 1 1 d . H1 H 0.5437 0.6284 0.7646 0.043 Uiso 1 1 calc R N2 N 0.55039(19) 0.33852(17) 0.83369(10) 0.0388(4) Uani 1 1 d . H2 H 0.4585 0.3103 0.8324 0.047 Uiso 1 1 calc R O1 O 0.25446(18) 0.48967(16) 0.74123(7) 0.0427(4) Uani 1 1 d . O2 O 0.77727(17) 0.30486(18) 0.80408(8) 0.0493(4) Uani 1 1 d . Cl1 Cl 0.19365(8) 0.31548(6) 0.91965(3) 0.05549(17) Uani 1 1 d . Cl2 Cl 0.03948(11) 0.55455(9) 0.89248(4) 0.0812(3) 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 0.0383(10) 0.0256(10) 0.0276(9) 0.0001(8) 0.0079(7) 0.0001(8) C1S 0.0419(12) 0.0578(16) 0.0415(12) -0.0077(11) 0.0036(9) -0.0052(11) C8 0.0397(11) 0.0242(10) 0.0391(11) -0.0010(8) -0.0080(8) -0.0065(8) C7 0.0751(18) 0.0554(17) 0.0424(13) 0.0148(12) -0.0204(12) -0.0267(14) C6 0.100(2) 0.080(2) 0.0302(11) -0.0083(13) -0.0035(13) -0.0366(18) C5 0.100(2) 0.070(2) 0.0521(15) -0.0401(15) 0.0367(15) -0.0362(17) C4 0.0624(15) 0.0266(11) 0.0594(15) -0.0123(10) 0.0221(12) -0.0066(10) C1 0.0307(9) 0.0235(9) 0.0286(9) 0.0015(7) 0.0077(7) 0.0027(7) C2 0.0286(9) 0.0293(10) 0.0284(9) 0.0050(8) -0.0025(7) -0.0046(8) C10 0.0280(9) 0.0255(10) 0.0277(9) 0.0024(7) 0.0081(7) 0.0008(7) C21 0.0287(9) 0.0299(10) 0.0277(9) 0.0037(7) 0.0077(7) 0.0032(8) C26 0.0320(10) 0.0280(10) 0.0348(10) 0.0035(8) 0.0046(8) 0.0026(8) C25 0.0353(11) 0.0340(12) 0.0523(13) 0.0043(10) 0.0081(9) -0.0044(9) C24 0.0279(10) 0.0448(14) 0.0642(14) 0.0048(11) 0.0115(10) -0.0003(9) C23 0.0324(11) 0.0416(13) 0.0616(15) 0.0133(11) 0.0117(10) 0.0107(9) C22 0.0315(10) 0.0336(11) 0.0467(12) 0.0111(9) 0.0114(8) 0.0039(8) C31 0.0348(9) 0.0267(10) 0.0272(9) 0.0026(7) 0.0087(7) 0.0005(8) C36 0.0422(11) 0.0339(12) 0.0402(11) -0.0026(9) 0.0131(9) 0.0042(9) C35 0.0671(16) 0.0365(13) 0.0445(12) -0.0077(10) 0.0166(11) 0.0082(11) C34 0.0697(16) 0.0292(11) 0.0380(11) -0.0021(9) 0.0052(11) -0.0100(11) C33 0.0457(12) 0.0458(14) 0.0389(11) 0.0014(10) 0.0053(9) -0.0119(10) C32 0.0362(10) 0.0465(13) 0.0336(10) -0.0058(9) 0.0082(8) -0.0022(9) C11 0.0229(9) 0.0274(10) 0.0330(9) 0.0012(7) 0.0041(7) 0.0000(7) C16 0.0324(10) 0.0350(11) 0.0313(10) 0.0006(8) 0.0042(8) 0.0034(8) C15 0.0357(11) 0.0401(12) 0.0380(11) 0.0077(9) -0.0013(8) 0.0037(9) C14 0.0350(10) 0.0305(11) 0.0551(13) 0.0057(10) -0.0028(9) 0.0073(9) C13 0.0351(10) 0.0298(11) 0.0509(13) -0.0055(9) 0.0065(9) 0.0057(9) C12 0.0304(9) 0.0307(10) 0.0333(10) -0.0025(8) 0.0040(7) -0.0002(8) C20 0.0255(9) 0.0232(9) 0.0326(9) 0.0038(8) 0.0020(7) -0.0014(7) C61 0.0265(9) 0.0214(9) 0.0340(9) -0.0036(7) 0.0046(7) -0.0021(7) C66 0.0321(10) 0.0257(10) 0.0364(10) 0.0000(8) 0.0050(8) -0.0012(8) C65 0.0345(10) 0.0339(11) 0.0426(11) -0.0022(9) 0.0134(9) -0.0091(8) C64 0.0265(9) 0.0416(12) 0.0463(11) -0.0113(10) 0.0089(8) -0.0053(9) C63 0.0277(10) 0.0310(11) 0.0448(11) -0.0078(9) -0.0013(8) -0.0006(8) C62 0.0277(10) 0.0237(9) 0.0418(10) -0.0015(8) 0.0011(8) -0.0014(7) C51 0.0293(9) 0.0207(9) 0.0353(10) 0.0055(7) 0.0038(7) 0.0013(7) C56 0.0302(9) 0.0334(11) 0.0357(10) 0.0051(8) 0.0022(8) -0.0011(8) C55 0.0413(11) 0.0388(12) 0.0339(10) 0.0029(9) -0.0005(8) 0.0017(9) C54 0.0478(12) 0.0332(11) 0.0373(11) 0.0081(9) 0.0111(9) 0.0073(9) C53 0.0385(11) 0.0351(12) 0.0513(13) 0.0049(10) 0.0178(10) 0.0007(9) C52 0.0319(10) 0.0294(11) 0.0456(11) 0.0001(9) 0.0075(9) -0.0024(8) C41 0.0246(9) 0.0319(11) 0.0396(11) 0.0116(8) 0.0056(8) 0.0005(8) C46 0.0342(10) 0.0309(11) 0.0464(12) 0.0088(9) -0.0014(9) -0.0023(9) C45 0.0408(12) 0.0338(12) 0.0602(14) 0.0137(10) 0.0034(10) 0.0051(9) C44 0.0442(12) 0.0486(15) 0.0570(15) 0.0253(12) -0.0021(10) 0.0096(11) C43 0.0657(16) 0.0635(18) 0.0386(12) 0.0146(12) -0.0032(11) 0.0141(14) C42 0.0517(13) 0.0507(14) 0.0385(11) 0.0109(10) 0.0065(10) 0.0124(11) N1 0.0290(8) 0.0486(11) 0.0295(8) 0.0075(8) 0.0054(6) -0.0049(7) N2 0.0279(8) 0.0259(9) 0.0615(12) -0.0077(8) -0.0021(8) -0.0044(7) O1 0.0449(8) 0.0531(10) 0.0316(7) -0.0036(7) 0.0112(6) -0.0198(8) O2 0.0390(8) 0.0581(11) 0.0522(9) -0.0200(8) 0.0117(7) -0.0221(8) Cl1 0.0728(4) 0.0476(3) 0.0443(3) -0.0014(3) -0.0055(3) 0.0059(3) Cl2 0.0979(6) 0.0728(5) 0.0703(5) -0.0119(4) -0.0074(4) 0.0430(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C3 C8 109.39(16) N1 C3 C4 109.52(18) C8 C3 C4 110.92(18) N1 C3 H3 109.0 C8 C3 H3 109.0 C4 C3 H3 109.0 Cl2 C1S Cl1 110.91(13) Cl2 C1S H1S1 109.5 Cl1 C1S H1S1 109.5 Cl2 C1S H1S2 109.5 Cl1 C1S H1S2 109.5 H1S1 C1S H1S2 108.0 N2 C8 C7 110.32(19) N2 C8 C3 109.20(16) C7 C8 C3 112.5(2) N2 C8 H8 108.2 C7 C8 H8 108.2 C3 C8 H8 108.2 C6 C7 C8 112.5(2) C6 C7 H7B 109.1 C8 C7 H7B 109.1 C6 C7 H7A 109.1 C8 C7 H7A 109.1 H7B C7 H7A 107.8 C5 C6 C7 109.2(2) C5 C6 H6B 109.8 C7 C6 H6B 109.8 C5 C6 H6A 109.8 C7 C6 H6A 109.8 H6B C6 H6A 108.3 C6 C5 C4 111.9(2) C6 C5 H5A 109.2 C4 C5 H5A 109.2 C6 C5 H5B 109.2 C4 C5 H5B 109.2 H5A C5 H5B 107.9 C3 C4 C5 111.2(2) C3 C4 H4B 109.4 C5 C4 H4B 109.4 C3 C4 H4A 109.4 C5 C4 H4A 109.4 H4B C4 H4A 108.0 O1 C1 N1 122.15(17) O1 C1 C10 121.98(17) N1 C1 C10 115.83(16) O2 C2 N2 121.6(2) O2 C2 C20 119.99(18) N2 C2 C20 118.31(16) C11 C10 C21 111.06(15) C11 C10 C31 107.43(15) C21 C10 C31 112.83(15) C11 C10 C1 107.75(14) C21 C10 C1 108.82(15) C31 C10 C1 108.81(15) C26 C21 C22 117.77(18) C26 C21 C10 122.16(17) C22 C21 C10 119.79(17) C25 C26 C21 120.72(19) C25 C26 H26 119.6 C21 C26 H26 119.6 C24 C25 C26 120.9(2) C24 C25 H25 119.6 C26 C25 H25 119.6 C25 C24 C23 119.3(2) C25 C24 H24 120.3 C23 C24 H24 120.3 C22 C23 C24 119.8(2) C22 C23 H23 120.1 C24 C23 H23 120.1 C23 C22 C21 121.5(2) C23 C22 H22 119.3 C21 C22 H22 119.3 C36 C31 C32 117.47(19) C36 C31 C10 123.40(18) C32 C31 C10 118.96(17) C31 C36 C35 120.4(2) C31 C36 H36 119.8 C35 C36 H36 119.8 C34 C35 C36 121.5(2) C34 C35 H35 119.3 C36 C35 H35 119.3 C35 C34 C33 118.7(2) C35 C34 H34 120.7 C33 C34 H34 120.7 C32 C33 C34 120.3(2) C32 C33 H33 119.8 C34 C33 H33 119.8 C33 C32 C31 121.7(2) C33 C32 H32 119.2 C31 C32 H32 119.2 C12 C11 C16 117.70(18) C12 C11 C10 124.08(17) C16 C11 C10 118.21(17) C15 C16 C11 121.53(19) C15 C16 H16 119.2 C11 C16 H16 119.2 C16 C15 C14 120.2(2) C16 C15 H15 119.9 C14 C15 H15 119.9 C13 C14 C15 119.2(2) C13 C14 H14 120.4 C15 C14 H14 120.4 C14 C13 C12 120.5(2) C14 C13 H13 119.7 C12 C13 H13 119.7 C11 C12 C13 120.85(19) C11 C12 H12 119.6 C13 C12 H12 119.6 C61 C20 C41 111.43(15) C61 C20 C51 111.15(15) C41 C20 C51 108.15(15) C61 C20 C2 110.74(15) C41 C20 C2 105.40(15) C51 C20 C2 109.79(15) C66 C61 C62 117.91(17) C66 C61 C20 122.25(17) C62 C61 C20 119.80(17) C65 C66 C61 120.42(19) C65 C66 H66 119.8 C61 C66 H66 119.8 C64 C65 C66 121.0(2) C64 C65 H65 119.5 C66 C65 H65 119.5 C65 C64 C63 119.29(18) C65 C64 H64 120.4 C63 C64 H64 120.4 C62 C63 C64 120.2(2) C62 C63 H63 119.9 C64 C63 H63 119.9 C63 C62 C61 121.23(19) C63 C62 H62 119.4 C61 C62 H62 119.4 C56 C51 C52 117.23(19) C56 C51 C20 122.22(16) C52 C51 C20 120.00(18) C55 C56 C51 121.31(19) C55 C56 H56 119.3 C51 C56 H56 119.3 C54 C55 C56 120.9(2) C54 C55 H55 119.6 C56 C55 H55 119.6 C55 C54 C53 118.6(2) C55 C54 H54 120.7 C53 C54 H54 120.7 C52 C53 C54 120.8(2) C52 C53 H53 119.6 C54 C53 H53 119.6 C53 C52 C51 121.2(2) C53 C52 H52 119.4 C51 C52 H52 119.4 C42 C41 C46 118.3(2) C42 C41 C20 120.9(2) C46 C41 C20 120.77(19) C41 C46 C45 120.5(2) C41 C46 H46 119.8 C45 C46 H46 119.8 C44 C45 C46 120.2(2) C44 C45 H45 119.9 C46 C45 H45 119.9 C43 C44 C45 119.5(2) C43 C44 H44 120.3 C45 C44 H44 120.3 C44 C43 C42 120.5(3) C44 C43 H43 119.8 C42 C43 H43 119.8 C41 C42 C43 121.1(3) C41 C42 H42 119.5 C43 C42 H42 119.5 C1 N1 C3 124.91(17) C1 N1 H1 117.5 C3 N1 H1 117.5 C2 N2 C8 123.75(18) C2 N2 H2 118.1 C8 N2 H2 118.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C3 N1 1.453(2) C3 C8 1.533(3) C3 C4 1.534(3) C3 H3 1.0000 C1S Cl2 1.753(3) C1S Cl1 1.784(3) C1S H1S1 0.9900 C1S H1S2 0.9900 C8 N2 1.464(3) C8 C7 1.511(3) C8 H8 1.0000 C7 C6 1.507(4) C7 H7B 0.9900 C7 H7A 0.9900 C6 C5 1.493(5) C6 H6B 0.9900 C6 H6A 0.9900 C5 C4 1.549(4) C5 H5A 0.9900 C5 H5B 0.9900 C4 H4B 0.9900 C4 H4A 0.9900 C1 O1 1.214(2) C1 N1 1.341(3) C1 C10 1.574(2) C2 O2 1.217(2) C2 N2 1.322(3) C2 C20 1.573(3) C10 C11 1.543(3) C10 C21 1.545(2) C10 C31 1.552(3) C21 C26 1.392(3) C21 C22 1.395(3) C26 C25 1.389(3) C26 H26 0.9500 C25 C24 1.373(3) C25 H25 0.9500 C24 C23 1.392(4) C24 H24 0.9500 C23 C22 1.384(3) C23 H23 0.9500 C22 H22 0.9500 C31 C36 1.390(3) C31 C32 1.393(3) C36 C35 1.391(3) C36 H36 0.9500 C35 C34 1.369(4) C35 H35 0.9500 C34 C33 1.384(4) C34 H34 0.9500 C33 C32 1.380(3) C33 H33 0.9500 C32 H32 0.9500 C11 C12 1.390(3) C11 C16 1.398(3) C16 C15 1.378(3) C16 H16 0.9500 C15 C14 1.388(3) C15 H15 0.9500 C14 C13 1.380(3) C14 H14 0.9500 C13 C12 1.392(3) C13 H13 0.9500 C12 H12 0.9500 C20 C61 1.539(2) C20 C41 1.544(3) C20 C51 1.552(3) C61 C66 1.399(3) C61 C62 1.400(3) C66 C65 1.392(3) C66 H66 0.9500 C65 C64 1.379(3) C65 H65 0.9500 C64 C63 1.388(3) C64 H64 0.9500 C63 C62 1.386(3) C63 H63 0.9500 C62 H62 0.9500 C51 C56 1.397(3) C51 C52 1.397(3) C56 C55 1.382(3) C56 H56 0.9500 C55 C54 1.380(3) C55 H55 0.9500 C54 C53 1.386(4) C54 H54 0.9500 C53 C52 1.383(3) C53 H53 0.9500 C52 H52 0.9500 C41 C42 1.386(3) C41 C46 1.392(3) C46 C45 1.397(3) C46 H46 0.9500 C45 C44 1.383(4) C45 H45 0.9500 C44 C43 1.372(4) C44 H44 0.9500 C43 C42 1.387(4) C43 H43 0.9500 C42 H42 0.9500 N1 H1 0.8800 N2 H2 0.8800 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 N1 C3 C8 N2 -65.5(2) C4 C3 C8 N2 173.63(18) N1 C3 C8 C7 171.72(18) C4 C3 C8 C7 50.8(2) N2 C8 C7 C6 -177.2(2) C3 C8 C7 C6 -55.0(3) C8 C7 C6 C5 58.1(3) C7 C6 C5 C4 -58.4(3) N1 C3 C4 C5 -171.6(2) C8 C3 C4 C5 -50.8(3) C6 C5 C4 C3 56.2(3) O1 C1 C10 C11 80.3(2) N1 C1 C10 C11 -97.49(19) O1 C1 C10 C21 -159.22(19) N1 C1 C10 C21 23.0(2) O1 C1 C10 C31 -35.9(2) N1 C1 C10 C31 146.32(17) C11 C10 C21 C26 5.0(2) C31 C10 C21 C26 125.6(2) C1 C10 C21 C26 -113.5(2) C11 C10 C21 C22 178.76(18) C31 C10 C21 C22 -60.6(2) C1 C10 C21 C22 60.3(2) C22 C21 C26 C25 -0.4(3) C10 C21 C26 C25 173.51(18) C21 C26 C25 C24 -0.7(3) C26 C25 C24 C23 1.6(4) C25 C24 C23 C22 -1.3(4) C24 C23 C22 C21 0.1(4) C26 C21 C22 C23 0.7(3) C10 C21 C22 C23 -173.4(2) C11 C10 C31 C36 119.8(2) C21 C10 C31 C36 -2.9(3) C1 C10 C31 C36 -123.8(2) C11 C10 C31 C32 -55.3(2) C21 C10 C31 C32 -177.99(18) C1 C10 C31 C32 61.1(2) C32 C31 C36 C35 -1.8(3) C10 C31 C36 C35 -176.9(2) C31 C36 C35 C34 1.3(4) C36 C35 C34 C33 -0.6(4) C35 C34 C33 C32 0.4(4) C34 C33 C32 C31 -0.9(4) C36 C31 C32 C33 1.6(3) C10 C31 C32 C33 177.0(2) C21 C10 C11 C12 -103.8(2) C31 C10 C11 C12 132.35(19) C1 C10 C11 C12 15.3(2) C21 C10 C11 C16 75.1(2) C31 C10 C11 C16 -48.7(2) C1 C10 C11 C16 -165.79(17) C12 C11 C16 C15 -0.2(3) C10 C11 C16 C15 -179.22(18) C11 C16 C15 C14 -0.7(3) C16 C15 C14 C13 0.8(3) C15 C14 C13 C12 0.0(3) C16 C11 C12 C13 1.0(3) C10 C11 C12 C13 179.96(18) C14 C13 C12 C11 -0.9(3) O2 C2 C20 C61 -178.18(18) N2 C2 C20 C61 5.5(2) O2 C2 C20 C41 61.2(2) N2 C2 C20 C41 -115.15(19) O2 C2 C20 C51 -55.1(2) N2 C2 C20 C51 128.59(18) C41 C20 C61 C66 3.2(3) C51 C20 C61 C66 123.90(19) C2 C20 C61 C66 -113.78(19) C41 C20 C61 C62 -178.86(17) C51 C20 C61 C62 -58.2(2) C2 C20 C61 C62 64.2(2) C62 C61 C66 C65 -0.5(3) C20 C61 C66 C65 177.53(18) C61 C66 C65 C64 -0.4(3) C66 C65 C64 C63 0.8(3) C65 C64 C63 C62 -0.4(3) C64 C63 C62 C61 -0.4(3) C66 C61 C62 C63 0.8(3) C20 C61 C62 C63 -177.19(18) C61 C20 C51 C56 -15.4(3) C41 C20 C51 C56 107.3(2) C2 C20 C51 C56 -138.22(19) C61 C20 C51 C52 173.40(18) C41 C20 C51 C52 -64.0(2) C2 C20 C51 C52 50.5(2) C52 C51 C56 C55 0.7(3) C20 C51 C56 C55 -170.81(19) C51 C56 C55 C54 0.3(3) C56 C55 C54 C53 -1.3(3) C55 C54 C53 C52 1.3(3) C54 C53 C52 C51 -0.3(3) C56 C51 C52 C53 -0.7(3) C20 C51 C52 C53 171.0(2) C61 C20 C41 C42 -85.7(2) C51 C20 C41 C42 151.80(19) C2 C20 C41 C42 34.4(2) C61 C20 C41 C46 93.0(2) C51 C20 C41 C46 -29.5(2) C2 C20 C41 C46 -146.84(18) C42 C41 C46 C45 -1.1(3) C20 C41 C46 C45 -179.85(19) C41 C46 C45 C44 0.4(3) C46 C45 C44 C43 0.4(4) C45 C44 C43 C42 -0.5(4) C46 C41 C42 C43 1.0(4) C20 C41 C42 C43 179.8(2) C44 C43 C42 C41 -0.2(4) O1 C1 N1 C3 7.5(3) C10 C1 N1 C3 -174.73(18) C8 C3 N1 C1 107.4(2) C4 C3 N1 C1 -130.8(2) O2 C2 N2 C8 -2.8(3) C20 C2 N2 C8 173.53(18) C7 C8 N2 C2 -101.3(3) C3 C8 N2 C2 134.6(2)