#------------------------------------------------------------------------------ #$Date: 2022-08-09 03:11:32 +0300 (Tue, 09 Aug 2022) $ #$Revision: 277161 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/52/7245278.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_7245278 loop_ _publ_author_name 'SCHLIMPEN, Fabian' 'AST, Tun' 'Benneteau, Valerie' 'Pale, Patrick' 'Chassaing, Stefan' _publ_section_title ; From A3/KA2 to AYA/KYA Multicomponent Coupling Reactions with Terminal Ynamides as Alkyne Surrogates - A Direct, Green Route to \g-Amino-Ynamides ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D2GC00966H _journal_year 2022 _chemical_absolute_configuration ad _chemical_formula_moiety 'C28 H30 N2 O3 S' _chemical_formula_sum 'C28 H30 N2 O3 S' _chemical_formula_weight 474.60 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2022-03-02 deposited with the CCDC. 2022-08-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 10.6469(3) _cell_length_b 15.8266(4) _cell_length_c 28.9384(7) _cell_measurement_reflns_used 9724 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 66.15 _cell_measurement_theta_min 3.19 _cell_volume 4876.2(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker PHOTON-III CPAD' _diffrn_measurement_method '\f and \w shuterless scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 52110 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 66.565 _diffrn_reflns_theta_max 66.565 _diffrn_reflns_theta_min 3.054 _diffrn_source 'Cu-ImuS 3.0 microfocus tube' _exptl_absorpt_coefficient_mu 1.438 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_correction_T_min 0.6327 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 2016 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: diethyl ether' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.298 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.039 _refine_ls_abs_structure_details ; Flack x determined using 3442 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.009(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 617 _refine_ls_number_reflns 8605 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0327 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+1.3595P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0886 _refine_ls_wR_factor_ref 0.0907 _reflns_Friedel_coverage 0.789 _reflns_Friedel_fraction_full 0.996 _reflns_Friedel_fraction_max 0.996 _reflns_number_gt 8115 _reflns_number_total 8605 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d2gc00966h2.cif _cod_data_source_block ea_b _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_crystal_density_meas' value 'none' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 7245278 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.762 _shelx_estimated_absorpt_t_max 0.870 _shelx_res_file ; TITL ea_b.res in P2(1)2(1)2(1) ea_b.res created by SHELXL-2018/3 at 14:02:15 on 06-Apr-2021 CELL 1.54178 10.6469 15.8266 28.9384 90.000 90.000 90.000 ZERR 8.000 0.0003 0.0004 0.0007 0.000 0.000 0.000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H N O S UNIT 224 240 16 24 8 L.S. 10 ACTA BOND $H FMAP 2 PLAN 10 CONF SIZE 0.10 0.20 0.20 TEMP -153.150 WGHT 0.050400 1.359500 FVAR 0.37706 N1 3 0.072149 0.954671 0.333910 11.00000 0.02497 0.01851 = 0.01916 -0.00032 -0.00366 0.00208 C1 1 0.104815 0.889458 0.362379 11.00000 0.02721 0.01931 = 0.01937 -0.00209 -0.00243 -0.00117 C2 1 0.139155 0.835068 0.387909 11.00000 0.02490 0.02302 = 0.02176 -0.00070 -0.00057 0.00012 C3 1 0.184269 0.767506 0.418717 11.00000 0.02373 0.02220 = 0.02227 0.00042 -0.00187 0.00201 AFIX 13 H3 2 0.277444 0.764009 0.414804 11.00000 -1.20000 AFIX 0 N2 3 0.132357 0.683444 0.407113 11.00000 0.03755 0.01913 = 0.02351 -0.00176 -0.00398 0.00827 C4 1 0.170032 0.650947 0.361272 11.00000 0.09122 0.03154 = 0.02121 -0.00291 -0.00457 0.02358 AFIX 13 H4 2 0.176658 0.698428 0.338603 11.00000 -1.20000 AFIX 0 C5 1 0.061006 0.591347 0.347818 11.00000 0.11848 0.04052 = 0.04927 -0.02002 -0.03926 0.01214 AFIX 23 H5A 2 0.022393 0.609774 0.318373 11.00000 -1.20000 H5B 2 0.091997 0.532775 0.344047 11.00000 -1.20000 AFIX 0 C6 1 -0.034639 0.595945 0.387042 11.00000 0.08354 0.03271 = 0.05391 -0.00149 -0.02962 -0.00985 AFIX 23 H6A 2 -0.121645 0.594578 0.374996 11.00000 -1.20000 H6B 2 -0.023066 0.548829 0.409138 11.00000 -1.20000 AFIX 0 C7 1 -0.005768 0.679546 0.409264 11.00000 0.03792 0.02623 = 0.04108 0.00402 -0.01242 -0.00603 AFIX 23 H7A 2 -0.044380 0.726725 0.391864 11.00000 -1.20000 H7B 2 -0.035812 0.681161 0.441628 11.00000 -1.20000 AFIX 0 C8 1 0.295605 0.607481 0.366584 11.00000 0.08765 0.04937 = 0.03742 0.00466 0.02181 0.03840 AFIX 23 H8A 2 0.316598 0.577263 0.337643 11.00000 -1.20000 H8B 2 0.361641 0.650290 0.372237 11.00000 -1.20000 AFIX 0 O1 4 0.292896 0.549160 0.403887 11.00000 0.08346 0.04945 = 0.04104 0.00784 0.01410 0.04014 AFIX 147 H1A 2 0.245126 0.567460 0.424708 11.00000 -1.50000 AFIX 0 C9 1 0.158942 0.785785 0.469644 11.00000 0.02337 0.02036 = 0.02236 0.00108 -0.00366 -0.00376 C10 1 0.225818 0.740013 0.502446 11.00000 0.02783 0.02708 = 0.02730 0.00452 -0.00395 0.00100 AFIX 43 H10 2 0.284447 0.698384 0.492748 11.00000 -1.20000 AFIX 0 C11 1 0.207638 0.754628 0.549105 11.00000 0.03637 0.03792 = 0.02521 0.00689 -0.00817 -0.00510 AFIX 43 H11 2 0.254058 0.723110 0.571216 11.00000 -1.20000 AFIX 0 C12 1 0.122383 0.814783 0.563756 11.00000 0.04003 0.04040 = 0.02188 -0.00259 -0.00019 -0.00809 AFIX 43 H12 2 0.109889 0.824499 0.595824 11.00000 -1.20000 AFIX 0 C13 1 0.055149 0.860897 0.531334 11.00000 0.03068 0.03251 = 0.03190 -0.00643 0.00060 0.00019 AFIX 43 H13 2 -0.003470 0.902389 0.541215 11.00000 -1.20000 AFIX 0 C14 1 0.073397 0.846501 0.484400 11.00000 0.02656 0.02633 = 0.02586 -0.00109 -0.00470 0.00171 AFIX 43 H14 2 0.027242 0.878270 0.462321 11.00000 -1.20000 AFIX 0 S1 5 0.123128 0.946714 0.279213 11.00000 0.02176 0.01940 = 0.01877 -0.00048 -0.00137 -0.00424 O2 4 0.244194 0.908607 0.281356 11.00000 0.02058 0.03344 = 0.02585 -0.00386 -0.00160 -0.00295 O3 4 0.107891 1.029309 0.259933 11.00000 0.03682 0.01946 = 0.02387 0.00220 -0.00286 -0.00920 C15 1 0.019025 0.877579 0.250830 11.00000 0.02225 0.01669 = 0.01618 -0.00082 -0.00073 -0.00460 C16 1 0.047983 0.791726 0.248125 11.00000 0.02683 0.02123 = 0.02295 0.00170 -0.00351 0.00065 AFIX 43 H16 2 0.122135 0.770077 0.262026 11.00000 -1.20000 AFIX 0 C17 1 -0.033767 0.738771 0.224727 11.00000 0.03236 0.01654 = 0.02605 -0.00016 0.00087 -0.00125 AFIX 43 H17 2 -0.014856 0.680257 0.222449 11.00000 -1.20000 AFIX 0 C18 1 -0.143237 0.769711 0.204466 11.00000 0.02865 0.02577 = 0.01688 -0.00156 0.00212 -0.00854 C19 1 -0.171072 0.855329 0.208353 11.00000 0.02130 0.02704 = 0.01832 0.00057 -0.00130 -0.00135 AFIX 43 H19 2 -0.245878 0.876887 0.194892 11.00000 -1.20000 AFIX 0 C20 1 -0.090458 0.909639 0.231750 11.00000 0.02482 0.01917 = 0.01877 0.00035 0.00080 0.00015 AFIX 43 H20 2 -0.110169 0.967946 0.234618 11.00000 -1.20000 AFIX 0 C21 1 -0.229698 0.711551 0.178017 11.00000 0.03623 0.03224 = 0.02370 -0.00526 -0.00131 -0.01225 AFIX 137 H21A 2 -0.198958 0.705255 0.146283 11.00000 -1.50000 H21B 2 -0.314547 0.735536 0.177514 11.00000 -1.50000 H21C 2 -0.231699 0.656118 0.193090 11.00000 -1.50000 AFIX 0 C22 1 -0.054813 0.993826 0.340201 11.00000 0.02229 0.02757 = 0.02619 0.00149 -0.00387 0.00471 AFIX 23 H22A 2 -0.120077 0.953968 0.329309 11.00000 -1.20000 H22B 2 -0.060525 1.045708 0.321205 11.00000 -1.20000 AFIX 0 C23 1 -0.079001 1.015626 0.389955 11.00000 0.02020 0.02190 = 0.02849 -0.00185 -0.00203 0.00532 C24 1 -0.015873 1.080567 0.411658 11.00000 0.02493 0.03737 = 0.04512 -0.01361 0.00465 -0.00694 AFIX 43 H24 2 0.045611 1.111897 0.395153 11.00000 -1.20000 AFIX 0 C25 1 -0.041358 1.100480 0.457298 11.00000 0.02878 0.05726 = 0.04763 -0.02868 -0.00410 -0.00072 AFIX 43 H25 2 0.004271 1.144419 0.472076 11.00000 -1.20000 AFIX 0 C26 1 -0.132680 1.056939 0.481549 11.00000 0.03330 0.05057 = 0.02821 -0.01063 -0.00152 0.01688 AFIX 43 H26 2 -0.149621 1.070442 0.512923 11.00000 -1.20000 AFIX 0 C27 1 -0.198626 0.993872 0.459680 11.00000 0.04279 0.03619 = 0.03603 0.00229 0.01360 0.00211 AFIX 43 H27 2 -0.262888 0.964485 0.475817 11.00000 -1.20000 AFIX 0 C28 1 -0.172046 0.973006 0.414445 11.00000 0.03262 0.02568 = 0.03649 -0.00114 0.00158 -0.00625 AFIX 43 H28 2 -0.217825 0.928978 0.399809 11.00000 -1.20000 AFIX 0 N3 3 0.570184 0.052016 0.335426 11.00000 0.02500 0.01911 = 0.02762 -0.00002 -0.00659 0.00006 C29 1 0.579849 0.123260 0.362576 11.00000 0.03284 0.02013 = 0.02721 0.00418 -0.00774 -0.00465 C30 1 0.581878 0.182490 0.388298 11.00000 0.03150 0.02483 = 0.02791 0.00565 -0.00216 -0.00403 C31 1 0.592945 0.255526 0.420490 11.00000 0.02486 0.02258 = 0.02805 0.00005 0.00051 -0.00042 AFIX 13 H31 2 0.508159 0.282503 0.422329 11.00000 -1.20000 AFIX 0 N4 3 0.680586 0.320197 0.403131 11.00000 0.02370 0.02016 = 0.02708 0.00031 -0.00034 -0.00238 C32 1 0.631828 0.368798 0.363749 11.00000 0.03059 0.02925 = 0.02767 -0.00011 0.00022 0.00150 AFIX 13 H32 2 0.594167 0.329146 0.340687 11.00000 -1.20000 AFIX 0 C33 1 0.750095 0.409563 0.342966 11.00000 0.03457 0.05841 = 0.04153 0.02045 0.00487 -0.00213 AFIX 23 H33A 2 0.754995 0.398546 0.309339 11.00000 -1.20000 H33B 2 0.749859 0.471400 0.348126 11.00000 -1.20000 AFIX 0 C34 1 0.860354 0.368077 0.368250 11.00000 0.03147 0.03895 = 0.03198 0.00290 0.00547 -0.00116 AFIX 23 H34A 2 0.928553 0.353431 0.346418 11.00000 -1.20000 H34B 2 0.894305 0.405985 0.392427 11.00000 -1.20000 AFIX 0 C35 1 0.803961 0.289625 0.389371 11.00000 0.02746 0.03067 = 0.03188 -0.00358 0.00230 -0.00008 AFIX 23 H35A 2 0.797522 0.243285 0.366514 11.00000 -1.20000 H35B 2 0.853207 0.270014 0.416335 11.00000 -1.20000 AFIX 0 C36 1 0.536020 0.435208 0.376657 11.00000 0.04002 0.02716 = 0.04593 0.00811 0.00503 0.00424 AFIX 23 H36A 2 0.566047 0.466989 0.403974 11.00000 -1.20000 H36B 2 0.526303 0.475605 0.350783 11.00000 -1.20000 AFIX 0 O4 4 0.416148 0.397261 0.386942 11.00000 0.04342 0.03395 = 0.06590 0.01192 0.01866 0.01418 AFIX 147 H4A 2 0.364781 0.435091 0.394516 11.00000 -1.50000 AFIX 0 C37 1 0.626382 0.225440 0.469309 11.00000 0.03049 0.02165 = 0.02582 -0.00083 0.00141 0.00233 C38 1 0.563942 0.155988 0.487018 11.00000 0.02743 0.02596 = 0.03496 -0.00174 -0.00091 -0.00078 AFIX 43 H38 2 0.509087 0.124449 0.467708 11.00000 -1.20000 AFIX 0 C39 1 0.580607 0.131979 0.532616 11.00000 0.03958 0.03257 = 0.03213 0.00194 0.01118 -0.00303 AFIX 43 H39 2 0.534936 0.085411 0.544729 11.00000 -1.20000 AFIX 0 C40 1 0.663721 0.175714 0.560608 11.00000 0.04512 0.03900 = 0.02052 -0.00144 0.00648 0.00474 AFIX 43 H40 2 0.675601 0.159199 0.591865 11.00000 -1.20000 AFIX 0 C41 1 0.729147 0.243517 0.542684 11.00000 0.02934 0.03201 = 0.02685 -0.00578 -0.00208 0.00109 AFIX 43 H41 2 0.786668 0.273493 0.561686 11.00000 -1.20000 AFIX 0 C42 1 0.711627 0.268147 0.497301 11.00000 0.03339 0.02626 = 0.02549 -0.00201 0.00262 -0.00197 AFIX 43 H42 2 0.757965 0.314406 0.485177 11.00000 -1.20000 AFIX 0 S2 5 0.628231 0.060312 0.281921 11.00000 0.02307 0.02249 = 0.03110 0.00159 -0.00185 0.00669 O5 4 0.747052 0.101389 0.286173 11.00000 0.02093 0.03995 = 0.04700 0.00754 -0.00146 0.00398 O6 4 0.619158 -0.022598 0.262537 11.00000 0.04097 0.02609 = 0.03885 -0.00430 0.00252 0.01373 C43 1 0.526839 0.127665 0.251408 11.00000 0.02163 0.02148 = 0.02045 -0.00124 0.00061 0.00392 C44 1 0.553212 0.213435 0.249193 11.00000 0.02408 0.02297 = 0.02736 0.00089 -0.00118 -0.00228 AFIX 43 H44 2 0.626719 0.235574 0.263324 11.00000 -1.20000 AFIX 0 C45 1 0.470706 0.266298 0.226056 11.00000 0.03384 0.01901 = 0.02747 0.00348 -0.00319 -0.00098 AFIX 43 H45 2 0.488322 0.325060 0.224351 11.00000 -1.20000 AFIX 0 C46 1 0.362727 0.234922 0.205317 11.00000 0.02814 0.02398 = 0.01643 0.00075 0.00161 0.00377 C47 1 0.337690 0.148648 0.208445 11.00000 0.02729 0.02621 = 0.02113 -0.00399 -0.00308 -0.00130 AFIX 43 H47 2 0.263702 0.126545 0.194640 11.00000 -1.20000 AFIX 0 C48 1 0.418834 0.094703 0.231324 11.00000 0.02786 0.01855 = 0.02394 -0.00227 0.00078 -0.00027 AFIX 43 H48 2 0.401009 0.035997 0.233280 11.00000 -1.20000 AFIX 0 C49 1 0.273459 0.292891 0.180361 11.00000 0.03596 0.03250 = 0.02192 0.00049 -0.00378 0.00748 AFIX 137 H49A 2 0.296279 0.351757 0.186678 11.00000 -1.50000 H49B 2 0.187582 0.282388 0.191111 11.00000 -1.50000 H49C 2 0.278408 0.282264 0.147048 11.00000 -1.50000 AFIX 0 C50 1 0.448012 0.005689 0.339906 11.00000 0.02752 0.02257 = 0.02975 -0.00176 -0.00618 -0.00365 AFIX 23 H50A 2 0.451908 -0.047381 0.321853 11.00000 -1.20000 H50B 2 0.379420 0.040824 0.327089 11.00000 -1.20000 AFIX 0 C51 1 0.420120 -0.014605 0.389892 11.00000 0.02385 0.01810 = 0.03208 -0.00073 -0.00486 -0.00384 C52 1 0.326774 0.028852 0.412984 11.00000 0.03446 0.02024 = 0.03725 0.00176 -0.00587 0.00195 AFIX 43 H52 2 0.281994 0.072318 0.397454 11.00000 -1.20000 AFIX 0 C53 1 0.297363 0.009874 0.458694 11.00000 0.03102 0.02500 = 0.04180 -0.00434 0.00138 -0.00058 AFIX 43 H53 2 0.232676 0.039989 0.474186 11.00000 -1.20000 AFIX 0 C54 1 0.363055 -0.053231 0.481452 11.00000 0.03105 0.03368 = 0.03891 0.00826 0.00027 -0.00641 AFIX 43 H54 2 0.345158 -0.065795 0.512870 11.00000 -1.20000 AFIX 0 C55 1 0.454831 -0.097721 0.458037 11.00000 0.02922 0.04120 = 0.05188 0.02085 0.00199 0.00638 AFIX 43 H55 2 0.498774 -0.141894 0.473290 11.00000 -1.20000 AFIX 0 C56 1 0.483256 -0.078561 0.412671 11.00000 0.02594 0.03343 = 0.04637 0.00864 0.00491 0.00628 AFIX 43 H56 2 0.546679 -0.109568 0.396998 11.00000 -1.20000 AFIX 0 HKLF 4 REM ea_b.res in P2(1)2(1)2(1) REM wR2 = 0.090691, GooF = S = 1.04302, Restrained GooF = 1.04302 for all data REM R1 = 0.032720 for 8115 Fo > 4sig(Fo) and 0.035625 for all 8605 data REM 617 parameters refined using 0 restraints END WGHT 0.0454 1.5680 REM Highest difference peak 0.298, deepest hole -0.306, 1-sigma level 0.039 Q1 1 0.7244 0.2321 0.4108 11.00000 0.05 0.30 Q2 1 0.4839 0.3749 0.4126 11.00000 0.05 0.29 Q3 1 0.6608 0.1609 0.3792 11.00000 0.05 0.29 Q4 1 0.1416 0.5969 0.3347 11.00000 0.05 0.28 Q5 1 0.6954 0.2138 0.4561 11.00000 0.05 0.27 Q6 1 0.6342 0.4061 0.3338 11.00000 0.05 0.25 Q7 1 0.5654 0.1002 0.2654 11.00000 0.05 0.22 Q8 1 0.0602 0.9067 0.2664 11.00000 0.05 0.22 Q9 1 0.7812 0.0894 0.2590 11.00000 0.05 0.21 Q10 1 -0.1399 0.8162 0.1987 11.00000 0.05 0.20 ; _shelx_res_checksum 41705 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.0721(2) 0.95467(14) 0.33391(7) 0.0209(5) Uani 1 1 d . . . . . C1 C 0.1048(3) 0.88946(16) 0.36238(9) 0.0220(6) Uani 1 1 d . . . . . C2 C 0.1392(2) 0.83507(16) 0.38791(9) 0.0232(5) Uani 1 1 d . . . . . C3 C 0.1843(2) 0.76751(16) 0.41872(9) 0.0227(5) Uani 1 1 d . . . . . H3 H 0.277444 0.764009 0.414804 0.027 Uiso 1 1 calc R U . . . N2 N 0.1324(2) 0.68344(14) 0.40711(8) 0.0267(5) Uani 1 1 d . . . . . C4 C 0.1700(4) 0.6509(2) 0.36127(11) 0.0480(10) Uani 1 1 d . . . . . H4 H 0.176658 0.698428 0.338603 0.058 Uiso 1 1 calc R U . . . C5 C 0.0610(5) 0.5913(3) 0.34782(14) 0.0694(14) Uani 1 1 d . . . . . H5A H 0.022393 0.609774 0.318373 0.083 Uiso 1 1 calc R U . . . H5B H 0.091997 0.532775 0.344047 0.083 Uiso 1 1 calc R U . . . C6 C -0.0346(4) 0.5959(2) 0.38704(14) 0.0567(11) Uani 1 1 d . . . . . H6A H -0.121645 0.594578 0.374996 0.068 Uiso 1 1 calc R U . . . H6B H -0.023066 0.548829 0.409138 0.068 Uiso 1 1 calc R U . . . C7 C -0.0058(3) 0.67955(19) 0.40926(11) 0.0351(7) Uani 1 1 d . . . . . H7A H -0.044380 0.726725 0.391864 0.042 Uiso 1 1 calc R U . . . H7B H -0.035812 0.681161 0.441628 0.042 Uiso 1 1 calc R U . . . C8 C 0.2956(5) 0.6075(3) 0.36658(12) 0.0581(12) Uani 1 1 d . . . . . H8A H 0.316598 0.577263 0.337643 0.070 Uiso 1 1 calc R U . . . H8B H 0.361641 0.650290 0.372237 0.070 Uiso 1 1 calc R U . . . O1 O 0.2929(3) 0.54916(16) 0.40389(8) 0.0580(7) Uani 1 1 d . . . . . H1A H 0.245126 0.567460 0.424708 0.087 Uiso 1 1 calc R U . . . C9 C 0.1589(2) 0.78579(17) 0.46964(9) 0.0220(5) Uani 1 1 d . . . . . C10 C 0.2258(3) 0.74001(19) 0.50245(10) 0.0274(6) Uani 1 1 d . . . . . H10 H 0.284447 0.698384 0.492748 0.033 Uiso 1 1 calc R U . . . C11 C 0.2076(3) 0.7546(2) 0.54911(10) 0.0332(7) Uani 1 1 d . . . . . H11 H 0.254058 0.723110 0.571216 0.040 Uiso 1 1 calc R U . . . C12 C 0.1224(3) 0.8148(2) 0.56376(10) 0.0341(7) Uani 1 1 d . . . . . H12 H 0.109889 0.824499 0.595824 0.041 Uiso 1 1 calc R U . . . C13 C 0.0551(3) 0.8609(2) 0.53133(10) 0.0317(7) Uani 1 1 d . . . . . H13 H -0.003470 0.902389 0.541215 0.038 Uiso 1 1 calc R U . . . C14 C 0.0734(3) 0.84650(18) 0.48440(10) 0.0263(6) Uani 1 1 d . . . . . H14 H 0.027242 0.878270 0.462321 0.032 Uiso 1 1 calc R U . . . S1 S 0.12313(6) 0.94671(4) 0.27921(2) 0.01998(14) Uani 1 1 d . . . . . O2 O 0.24419(17) 0.90861(12) 0.28136(6) 0.0266(4) Uani 1 1 d . . . . . O3 O 0.10789(19) 1.02931(12) 0.25993(6) 0.0267(4) Uani 1 1 d . . . . . C15 C 0.0190(2) 0.87758(16) 0.25083(9) 0.0184(5) Uani 1 1 d . . . . . C16 C 0.0480(3) 0.79173(17) 0.24813(9) 0.0237(6) Uani 1 1 d . . . . . H16 H 0.122135 0.770077 0.262026 0.028 Uiso 1 1 calc R U . . . C17 C -0.0338(3) 0.73877(17) 0.22473(10) 0.0250(6) Uani 1 1 d . . . . . H17 H -0.014856 0.680257 0.222449 0.030 Uiso 1 1 calc R U . . . C18 C -0.1432(3) 0.76971(17) 0.20447(9) 0.0238(6) Uani 1 1 d . . . . . C19 C -0.1711(3) 0.85533(17) 0.20835(9) 0.0222(5) Uani 1 1 d . . . . . H19 H -0.245878 0.876887 0.194892 0.027 Uiso 1 1 calc R U . . . C20 C -0.0905(2) 0.90964(16) 0.23175(8) 0.0209(5) Uani 1 1 d . . . . . H20 H -0.110169 0.967946 0.234618 0.025 Uiso 1 1 calc R U . . . C21 C -0.2297(3) 0.71155(19) 0.17802(10) 0.0307(7) Uani 1 1 d . . . . . H21A H -0.198958 0.705255 0.146283 0.046 Uiso 1 1 calc R U . . . H21B H -0.314547 0.735536 0.177514 0.046 Uiso 1 1 calc R U . . . H21C H -0.231699 0.656118 0.193090 0.046 Uiso 1 1 calc R U . . . C22 C -0.0548(3) 0.99383(18) 0.34020(10) 0.0254(6) Uani 1 1 d . . . . . H22A H -0.120077 0.953968 0.329309 0.030 Uiso 1 1 calc R U . . . H22B H -0.060525 1.045708 0.321205 0.030 Uiso 1 1 calc R U . . . C23 C -0.0790(3) 1.01563(17) 0.38995(10) 0.0235(6) Uani 1 1 d . . . . . C24 C -0.0159(3) 1.0806(2) 0.41166(12) 0.0358(7) Uani 1 1 d . . . . . H24 H 0.045611 1.111897 0.395153 0.043 Uiso 1 1 calc R U . . . C25 C -0.0414(3) 1.1005(2) 0.45730(12) 0.0446(9) Uani 1 1 d . . . . . H25 H 0.004271 1.144419 0.472076 0.053 Uiso 1 1 calc R U . . . C26 C -0.1327(3) 1.0569(2) 0.48155(10) 0.0374(7) Uani 1 1 d . . . . . H26 H -0.149621 1.070442 0.512923 0.045 Uiso 1 1 calc R U . . . C27 C -0.1986(3) 0.9939(2) 0.45968(12) 0.0383(8) Uani 1 1 d . . . . . H27 H -0.262888 0.964485 0.475817 0.046 Uiso 1 1 calc R U . . . C28 C -0.1720(3) 0.97301(19) 0.41445(11) 0.0316(6) Uani 1 1 d . . . . . H28 H -0.217825 0.928978 0.399809 0.038 Uiso 1 1 calc R U . . . N3 N 0.5702(2) 0.05202(15) 0.33543(8) 0.0239(5) Uani 1 1 d . . . . . C29 C 0.5798(3) 0.12326(17) 0.36258(10) 0.0267(6) Uani 1 1 d . . . . . C30 C 0.5819(3) 0.18249(17) 0.38830(10) 0.0281(6) Uani 1 1 d . . . . . C31 C 0.5929(3) 0.25553(17) 0.42049(9) 0.0252(5) Uani 1 1 d . . . . . H31 H 0.508159 0.282503 0.422329 0.030 Uiso 1 1 calc R U . . . N4 N 0.6806(2) 0.32020(14) 0.40313(8) 0.0236(5) Uani 1 1 d . . . . . C32 C 0.6318(3) 0.36880(18) 0.36375(10) 0.0292(6) Uani 1 1 d . . . . . H32 H 0.594167 0.329146 0.340687 0.035 Uiso 1 1 calc R U . . . C33 C 0.7501(3) 0.4096(2) 0.34297(12) 0.0448(8) Uani 1 1 d . . . . . H33A H 0.754995 0.398546 0.309339 0.054 Uiso 1 1 calc R U . . . H33B H 0.749859 0.471400 0.348126 0.054 Uiso 1 1 calc R U . . . C34 C 0.8604(3) 0.3681(2) 0.36825(10) 0.0341(7) Uani 1 1 d . . . . . H34A H 0.928553 0.353431 0.346418 0.041 Uiso 1 1 calc R U . . . H34B H 0.894305 0.405985 0.392427 0.041 Uiso 1 1 calc R U . . . C35 C 0.8040(3) 0.28963(18) 0.38937(10) 0.0300(6) Uani 1 1 d . . . . . H35A H 0.797522 0.243285 0.366514 0.036 Uiso 1 1 calc R U . . . H35B H 0.853207 0.270014 0.416335 0.036 Uiso 1 1 calc R U . . . C36 C 0.5360(3) 0.4352(2) 0.37666(12) 0.0377(7) Uani 1 1 d . . . . . H36A H 0.566047 0.466989 0.403974 0.045 Uiso 1 1 calc R U . . . H36B H 0.526303 0.475605 0.350783 0.045 Uiso 1 1 calc R U . . . O4 O 0.4161(2) 0.39726(15) 0.38694(10) 0.0478(6) Uani 1 1 d . . . . . H4A H 0.364781 0.435091 0.394516 0.072 Uiso 1 1 calc R U . . . C37 C 0.6264(3) 0.22544(17) 0.46931(9) 0.0260(6) Uani 1 1 d . . . . . C38 C 0.5639(3) 0.15599(18) 0.48702(10) 0.0295(6) Uani 1 1 d . . . . . H38 H 0.509087 0.124449 0.467708 0.035 Uiso 1 1 calc R U . . . C39 C 0.5806(3) 0.1320(2) 0.53262(11) 0.0348(7) Uani 1 1 d . . . . . H39 H 0.534936 0.085411 0.544729 0.042 Uiso 1 1 calc R U . . . C40 C 0.6637(3) 0.1757(2) 0.56061(10) 0.0349(7) Uani 1 1 d . . . . . H40 H 0.675601 0.159199 0.591865 0.042 Uiso 1 1 calc R U . . . C41 C 0.7291(3) 0.24352(19) 0.54268(10) 0.0294(6) Uani 1 1 d . . . . . H41 H 0.786668 0.273493 0.561686 0.035 Uiso 1 1 calc R U . . . C42 C 0.7116(3) 0.26815(18) 0.49730(10) 0.0284(6) Uani 1 1 d . . . . . H42 H 0.757965 0.314406 0.485177 0.034 Uiso 1 1 calc R U . . . S2 S 0.62823(6) 0.06031(4) 0.28192(2) 0.02555(16) Uani 1 1 d . . . . . O5 O 0.74705(19) 0.10139(14) 0.28617(8) 0.0360(5) Uani 1 1 d . . . . . O6 O 0.6192(2) -0.02260(13) 0.26254(8) 0.0353(5) Uani 1 1 d . . . . . C43 C 0.5268(3) 0.12766(17) 0.25141(9) 0.0212(5) Uani 1 1 d . . . . . C44 C 0.5532(3) 0.21344(17) 0.24919(9) 0.0248(6) Uani 1 1 d . . . . . H44 H 0.626719 0.235574 0.263324 0.030 Uiso 1 1 calc R U . . . C45 C 0.4707(3) 0.26630(17) 0.22606(10) 0.0268(6) Uani 1 1 d . . . . . H45 H 0.488322 0.325060 0.224351 0.032 Uiso 1 1 calc R U . . . C46 C 0.3627(3) 0.23492(17) 0.20532(9) 0.0229(5) Uani 1 1 d . . . . . C47 C 0.3377(3) 0.14865(17) 0.20844(9) 0.0249(6) Uani 1 1 d . . . . . H47 H 0.263702 0.126545 0.194640 0.030 Uiso 1 1 calc R U . . . C48 C 0.4188(3) 0.09470(17) 0.23132(9) 0.0235(6) Uani 1 1 d . . . . . H48 H 0.401009 0.035997 0.233280 0.028 Uiso 1 1 calc R U . . . C49 C 0.2735(3) 0.29289(19) 0.18036(9) 0.0301(7) Uani 1 1 d . . . . . H49A H 0.296279 0.351757 0.186678 0.045 Uiso 1 1 calc R U . . . H49B H 0.187582 0.282388 0.191111 0.045 Uiso 1 1 calc R U . . . H49C H 0.278408 0.282264 0.147048 0.045 Uiso 1 1 calc R U . . . C50 C 0.4480(3) 0.00569(17) 0.33991(10) 0.0266(6) Uani 1 1 d . . . . . H50A H 0.451908 -0.047381 0.321853 0.032 Uiso 1 1 calc R U . . . H50B H 0.379420 0.040824 0.327089 0.032 Uiso 1 1 calc R U . . . C51 C 0.4201(3) -0.01461(17) 0.38989(10) 0.0247(6) Uani 1 1 d . . . . . C52 C 0.3268(3) 0.02885(18) 0.41298(11) 0.0307(6) Uani 1 1 d . . . . . H52 H 0.281994 0.072318 0.397454 0.037 Uiso 1 1 calc R U . . . C53 C 0.2974(3) 0.00987(19) 0.45869(12) 0.0326(7) Uani 1 1 d . . . . . H53 H 0.232676 0.039989 0.474186 0.039 Uiso 1 1 calc R U . . . C54 C 0.3631(3) -0.0532(2) 0.48145(11) 0.0345(7) Uani 1 1 d . . . . . H54 H 0.345158 -0.065795 0.512870 0.041 Uiso 1 1 calc R U . . . C55 C 0.4548(3) -0.0977(2) 0.45804(12) 0.0408(8) Uani 1 1 d . . . . . H55 H 0.498774 -0.141894 0.473290 0.049 Uiso 1 1 calc R U . . . C56 C 0.4833(3) -0.0786(2) 0.41267(11) 0.0352(7) Uani 1 1 d . . . . . H56 H 0.546679 -0.109568 0.396998 0.042 Uiso 1 1 calc R U . . . 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 N1 0.0250(11) 0.0185(11) 0.0192(10) -0.0003(9) -0.0037(9) 0.0021(9) C1 0.0272(14) 0.0193(12) 0.0194(12) -0.0021(10) -0.0024(10) -0.0012(11) C2 0.0249(14) 0.0230(13) 0.0218(12) -0.0007(11) -0.0006(11) 0.0001(10) C3 0.0237(13) 0.0222(12) 0.0223(12) 0.0004(10) -0.0019(10) 0.0020(10) N2 0.0376(13) 0.0191(11) 0.0235(11) -0.0018(9) -0.0040(10) 0.0083(10) C4 0.091(3) 0.0315(17) 0.0212(14) -0.0029(13) -0.0046(16) 0.0236(18) C5 0.118(4) 0.041(2) 0.049(2) -0.0200(18) -0.039(3) 0.012(2) C6 0.084(3) 0.0327(18) 0.054(2) -0.0015(17) -0.030(2) -0.0099(19) C7 0.0379(17) 0.0262(15) 0.0411(16) 0.0040(13) -0.0124(14) -0.0060(12) C8 0.088(3) 0.049(2) 0.0374(18) 0.0047(16) 0.022(2) 0.038(2) O1 0.083(2) 0.0495(15) 0.0410(12) 0.0078(11) 0.0141(13) 0.0401(14) C9 0.0234(13) 0.0204(12) 0.0224(12) 0.0011(10) -0.0037(10) -0.0038(10) C10 0.0278(15) 0.0271(14) 0.0273(13) 0.0045(12) -0.0040(11) 0.0010(12) C11 0.0364(16) 0.0379(17) 0.0252(13) 0.0069(13) -0.0082(12) -0.0051(13) C12 0.0400(16) 0.0404(16) 0.0219(13) -0.0026(12) -0.0002(13) -0.0081(14) C13 0.0307(16) 0.0325(16) 0.0319(15) -0.0064(13) 0.0006(12) 0.0002(12) C14 0.0266(14) 0.0263(14) 0.0259(13) -0.0011(11) -0.0047(11) 0.0017(11) S1 0.0218(3) 0.0194(3) 0.0188(3) -0.0005(2) -0.0014(2) -0.0042(2) O2 0.0206(9) 0.0334(10) 0.0259(9) -0.0039(8) -0.0016(8) -0.0030(8) O3 0.0368(11) 0.0195(9) 0.0239(9) 0.0022(8) -0.0029(8) -0.0092(8) C15 0.0223(13) 0.0167(12) 0.0162(12) -0.0008(10) -0.0007(10) -0.0046(10) C16 0.0268(14) 0.0212(13) 0.0230(13) 0.0017(11) -0.0035(11) 0.0007(11) C17 0.0324(14) 0.0165(12) 0.0261(13) -0.0002(11) 0.0009(11) -0.0012(11) C18 0.0286(14) 0.0258(13) 0.0169(12) -0.0016(10) 0.0021(10) -0.0085(11) C19 0.0213(13) 0.0270(14) 0.0183(12) 0.0006(11) -0.0013(10) -0.0014(11) C20 0.0248(14) 0.0192(12) 0.0188(12) 0.0003(10) 0.0008(10) 0.0002(10) C21 0.0362(16) 0.0322(16) 0.0237(13) -0.0053(12) -0.0013(12) -0.0123(13) C22 0.0223(15) 0.0276(15) 0.0262(15) 0.0015(11) -0.0039(11) 0.0047(11) C23 0.0202(13) 0.0219(13) 0.0285(14) -0.0018(12) -0.0020(11) 0.0053(11) C24 0.0249(15) 0.0374(17) 0.0451(18) -0.0136(15) 0.0046(13) -0.0069(13) C25 0.0288(16) 0.057(2) 0.0476(19) -0.0287(18) -0.0041(15) -0.0007(16) C26 0.0333(16) 0.0506(19) 0.0282(15) -0.0106(14) -0.0015(13) 0.0169(16) C27 0.0428(19) 0.0362(18) 0.0360(17) 0.0023(14) 0.0136(15) 0.0021(15) C28 0.0326(16) 0.0257(14) 0.0365(16) -0.0011(13) 0.0016(13) -0.0062(12) N3 0.0250(12) 0.0191(11) 0.0276(12) 0.0000(9) -0.0066(9) 0.0001(10) C29 0.0328(15) 0.0201(13) 0.0272(14) 0.0042(11) -0.0077(11) -0.0047(11) C30 0.0315(14) 0.0248(14) 0.0279(13) 0.0057(12) -0.0022(12) -0.0040(12) C31 0.0249(13) 0.0226(13) 0.0280(13) 0.0000(11) 0.0005(11) -0.0004(11) N4 0.0237(11) 0.0202(10) 0.0271(11) 0.0003(9) -0.0003(9) -0.0024(9) C32 0.0306(15) 0.0293(14) 0.0277(14) -0.0001(11) 0.0002(12) 0.0015(12) C33 0.0346(17) 0.058(2) 0.0415(17) 0.0204(17) 0.0049(14) -0.0021(16) C34 0.0315(16) 0.0389(16) 0.0320(15) 0.0029(13) 0.0055(12) -0.0012(13) C35 0.0275(14) 0.0307(14) 0.0319(14) -0.0036(12) 0.0023(12) -0.0001(12) C36 0.0400(17) 0.0272(15) 0.0459(18) 0.0081(13) 0.0050(14) 0.0042(13) O4 0.0434(14) 0.0339(12) 0.0659(16) 0.0119(12) 0.0187(12) 0.0142(10) C37 0.0305(14) 0.0217(12) 0.0258(13) -0.0008(11) 0.0014(11) 0.0023(12) C38 0.0274(15) 0.0260(15) 0.0350(15) -0.0017(12) -0.0009(13) -0.0008(12) C39 0.0396(17) 0.0326(16) 0.0321(15) 0.0019(13) 0.0112(13) -0.0030(13) C40 0.0451(18) 0.0390(17) 0.0205(13) -0.0014(12) 0.0065(12) 0.0047(14) C41 0.0293(15) 0.0320(15) 0.0269(14) -0.0058(12) -0.0021(11) 0.0011(12) C42 0.0334(15) 0.0263(15) 0.0255(13) -0.0020(12) 0.0026(11) -0.0020(12) S2 0.0231(3) 0.0225(3) 0.0311(3) 0.0016(3) -0.0019(3) 0.0067(3) O5 0.0209(10) 0.0399(12) 0.0470(13) 0.0075(10) -0.0015(9) 0.0040(9) O6 0.0410(12) 0.0261(10) 0.0388(11) -0.0043(9) 0.0025(10) 0.0137(9) C43 0.0216(13) 0.0215(13) 0.0205(13) -0.0012(10) 0.0006(10) 0.0039(10) C44 0.0241(14) 0.0230(13) 0.0274(14) 0.0009(11) -0.0012(11) -0.0023(11) C45 0.0338(15) 0.0190(13) 0.0275(14) 0.0035(11) -0.0032(12) -0.0010(11) C46 0.0281(14) 0.0240(13) 0.0164(11) 0.0007(10) 0.0016(10) 0.0038(11) C47 0.0273(14) 0.0262(14) 0.0211(12) -0.0040(11) -0.0031(10) -0.0013(11) C48 0.0279(14) 0.0186(12) 0.0239(13) -0.0023(11) 0.0008(11) -0.0003(11) C49 0.0360(17) 0.0325(16) 0.0219(13) 0.0005(12) -0.0038(12) 0.0075(13) C50 0.0275(15) 0.0226(14) 0.0298(16) -0.0018(11) -0.0062(12) -0.0037(12) C51 0.0238(14) 0.0181(12) 0.0321(15) -0.0007(12) -0.0049(12) -0.0038(11) C52 0.0345(16) 0.0202(13) 0.0373(16) 0.0018(13) -0.0059(13) 0.0019(12) C53 0.0310(16) 0.0250(15) 0.0418(18) -0.0043(13) 0.0014(14) -0.0006(13) C54 0.0310(16) 0.0337(16) 0.0389(16) 0.0083(13) 0.0003(13) -0.0064(14) C55 0.0292(16) 0.0412(18) 0.052(2) 0.0209(16) 0.0020(14) 0.0064(14) C56 0.0259(15) 0.0334(17) 0.0464(18) 0.0086(15) 0.0049(14) 0.0063(13) 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' S S 0.3331 0.5567 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C22 118.0(2) . . ? C1 N1 S1 115.46(18) . . ? C22 N1 S1 115.95(17) . . ? C2 C1 N1 176.3(3) . . ? C1 C2 C3 178.6(3) . . ? C2 C3 N2 113.2(2) . . ? C2 C3 C9 112.9(2) . . ? N2 C3 C9 108.9(2) . . ? C2 C3 H3 107.2 . . ? N2 C3 H3 107.2 . . ? C9 C3 H3 107.2 . . ? C7 N2 C4 107.1(3) . . ? C7 N2 C3 113.6(2) . . ? C4 N2 C3 114.5(2) . . ? N2 C4 C8 107.9(3) . . ? N2 C4 C5 103.6(3) . . ? C8 C4 C5 114.3(3) . . ? N2 C4 H4 110.3 . . ? C8 C4 H4 110.3 . . ? C5 C4 H4 110.3 . . ? C6 C5 C4 106.5(3) . . ? C6 C5 H5A 110.4 . . ? C4 C5 H5A 110.4 . . ? C6 C5 H5B 110.4 . . ? C4 C5 H5B 110.4 . . ? H5A C5 H5B 108.6 . . ? C7 C6 C5 102.9(3) . . ? C7 C6 H6A 111.2 . . ? C5 C6 H6A 111.2 . . ? C7 C6 H6B 111.2 . . ? C5 C6 H6B 111.2 . . ? H6A C6 H6B 109.1 . . ? N2 C7 C6 102.9(3) . . ? N2 C7 H7A 111.2 . . ? C6 C7 H7A 111.2 . . ? N2 C7 H7B 111.2 . . ? C6 C7 H7B 111.2 . . ? H7A C7 H7B 109.1 . . ? O1 C8 C4 110.8(3) . . ? O1 C8 H8A 109.5 . . ? C4 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C8 O1 H1A 109.5 . . ? C10 C9 C14 119.1(3) . . ? C10 C9 C3 118.0(2) . . ? C14 C9 C3 122.9(2) . . ? C11 C10 C9 120.5(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 120.4(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.6(3) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 120.1(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C9 120.3(3) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? O2 S1 O3 120.43(12) . . ? O2 S1 N1 106.46(11) . . ? O3 S1 N1 105.23(11) . . ? O2 S1 C15 109.08(12) . . ? O3 S1 C15 108.33(12) . . ? N1 S1 C15 106.44(12) . . ? C20 C15 C16 121.3(2) . . ? C20 C15 S1 119.19(19) . . ? C16 C15 S1 119.5(2) . . ? C17 C16 C15 118.5(3) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? C16 C17 C18 121.2(3) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C19 C18 C17 119.1(2) . . ? C19 C18 C21 120.3(3) . . ? C17 C18 C21 120.6(3) . . ? C20 C19 C18 120.6(3) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C15 C20 C19 119.1(2) . . ? C15 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N1 C22 C23 111.5(2) . . ? N1 C22 H22A 109.3 . . ? C23 C22 H22A 109.3 . . ? N1 C22 H22B 109.3 . . ? C23 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? C24 C23 C28 118.4(3) . . ? C24 C23 C22 121.6(3) . . ? C28 C23 C22 119.9(3) . . ? C23 C24 C25 120.6(3) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C26 C25 C24 120.6(3) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C27 C26 C25 119.2(3) . . ? C27 C26 H26 120.4 . . ? C25 C26 H26 120.4 . . ? C26 C27 C28 120.4(3) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C23 120.9(3) . . ? C27 C28 H28 119.6 . . ? C23 C28 H28 119.6 . . ? C29 N3 C50 114.6(2) . . ? C29 N3 S2 115.85(19) . . ? C50 N3 S2 116.05(18) . . ? C30 C29 N3 175.2(3) . . ? C29 C30 C31 176.5(3) . . ? N4 C31 C30 112.1(2) . . ? N4 C31 C37 112.5(2) . . ? C30 C31 C37 110.7(2) . . ? N4 C31 H31 107.1 . . ? C30 C31 H31 107.1 . . ? C37 C31 H31 107.1 . . ? C35 N4 C32 106.3(2) . . ? C35 N4 C31 115.7(2) . . ? C32 N4 C31 113.8(2) . . ? N4 C32 C36 114.2(2) . . ? N4 C32 C33 103.5(2) . . ? C36 C32 C33 111.0(3) . . ? N4 C32 H32 109.3 . . ? C36 C32 H32 109.3 . . ? C33 C32 H32 109.3 . . ? C34 C33 C32 105.1(2) . . ? C34 C33 H33A 110.7 . . ? C32 C33 H33A 110.7 . . ? C34 C33 H33B 110.7 . . ? C32 C33 H33B 110.7 . . ? H33A C33 H33B 108.8 . . ? C35 C34 C33 104.0(3) . . ? C35 C34 H34A 111.0 . . ? C33 C34 H34A 111.0 . . ? C35 C34 H34B 111.0 . . ? C33 C34 H34B 111.0 . . ? H34A C34 H34B 109.0 . . ? N4 C35 C34 101.3(2) . . ? N4 C35 H35A 111.5 . . ? C34 C35 H35A 111.5 . . ? N4 C35 H35B 111.5 . . ? C34 C35 H35B 111.5 . . ? H35A C35 H35B 109.3 . . ? O4 C36 C32 111.0(3) . . ? O4 C36 H36A 109.4 . . ? C32 C36 H36A 109.4 . . ? O4 C36 H36B 109.4 . . ? C32 C36 H36B 109.4 . . ? H36A C36 H36B 108.0 . . ? C36 O4 H4A 109.5 . . ? C38 C37 C42 118.9(3) . . ? C38 C37 C31 118.5(3) . . ? C42 C37 C31 122.5(2) . . ? C37 C38 C39 120.6(3) . . ? C37 C38 H38 119.7 . . ? C39 C38 H38 119.7 . . ? C38 C39 C40 120.1(3) . . ? C38 C39 H39 119.9 . . ? C40 C39 H39 119.9 . . ? C41 C40 C39 119.4(3) . . ? C41 C40 H40 120.3 . . ? C39 C40 H40 120.3 . . ? C40 C41 C42 120.5(3) . . ? C40 C41 H41 119.7 . . ? C42 C41 H41 119.7 . . ? C41 C42 C37 120.3(3) . . ? C41 C42 H42 119.9 . . ? C37 C42 H42 119.9 . . ? O5 S2 O6 120.76(13) . . ? O5 S2 N3 106.46(13) . . ? O6 S2 N3 105.43(13) . . ? O5 S2 C43 108.17(13) . . ? O6 S2 C43 108.56(13) . . ? N3 S2 C43 106.63(12) . . ? C44 C43 C48 121.0(2) . . ? C44 C43 S2 119.5(2) . . ? C48 C43 S2 119.4(2) . . ? C45 C44 C43 119.0(3) . . ? C45 C44 H44 120.5 . . ? C43 C44 H44 120.5 . . ? C44 C45 C46 121.2(3) . . ? C44 C45 H45 119.4 . . ? C46 C45 H45 119.4 . . ? C45 C46 C47 118.7(3) . . ? C45 C46 C49 120.8(2) . . ? C47 C46 C49 120.5(3) . . ? C48 C47 C46 121.1(3) . . ? C48 C47 H47 119.5 . . ? C46 C47 H47 119.5 . . ? C47 C48 C43 119.0(2) . . ? C47 C48 H48 120.5 . . ? C43 C48 H48 120.5 . . ? C46 C49 H49A 109.5 . . ? C46 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C46 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? N3 C50 C51 110.9(2) . . ? N3 C50 H50A 109.5 . . ? C51 C50 H50A 109.5 . . ? N3 C50 H50B 109.5 . . ? C51 C50 H50B 109.5 . . ? H50A C50 H50B 108.0 . . ? C52 C51 C56 118.9(3) . . ? C52 C51 C50 119.9(3) . . ? C56 C51 C50 121.1(3) . . ? C51 C52 C53 120.9(3) . . ? C51 C52 H52 119.5 . . ? C53 C52 H52 119.5 . . ? C54 C53 C52 119.6(3) . . ? C54 C53 H53 120.2 . . ? C52 C53 H53 120.2 . . ? C55 C54 C53 119.4(3) . . ? C55 C54 H54 120.3 . . ? C53 C54 H54 120.3 . . ? C56 C55 C54 120.6(3) . . ? C56 C55 H55 119.7 . . ? C54 C55 H55 119.7 . . ? C55 C56 C51 120.5(3) . . ? C55 C56 H56 119.8 . . ? C51 C56 H56 119.8 . . ? 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 N1 C1 1.366(3) . ? N1 C22 1.498(3) . ? N1 S1 1.678(2) . ? C1 C2 1.192(4) . ? C2 C3 1.473(3) . ? C3 N2 1.479(3) . ? C3 C9 1.526(3) . ? C3 H3 1.0000 . ? N2 C7 1.473(4) . ? N2 C4 1.478(4) . ? C4 C8 1.511(5) . ? C4 C5 1.546(6) . ? C4 H4 1.0000 . ? C5 C6 1.527(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.503(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O1 1.421(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? O1 H1A 0.8400 . ? C9 C10 1.390(4) . ? C9 C14 1.391(4) . ? C10 C11 1.384(4) . ? C10 H10 0.9500 . ? C11 C12 1.382(5) . ? C11 H11 0.9500 . ? C12 C13 1.388(4) . ? C12 H12 0.9500 . ? C13 C14 1.391(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? S1 O2 1.424(2) . ? S1 O3 1.431(2) . ? S1 C15 1.761(3) . ? C15 C20 1.386(4) . ? C15 C16 1.396(4) . ? C16 C17 1.385(4) . ? C16 H16 0.9500 . ? C17 C18 1.394(4) . ? C17 H17 0.9500 . ? C18 C19 1.392(4) . ? C18 C21 1.510(4) . ? C19 C20 1.391(4) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.503(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.379(4) . ? C23 C28 1.392(4) . ? C24 C25 1.385(5) . ? C24 H24 0.9500 . ? C25 C26 1.383(5) . ? C25 H25 0.9500 . ? C26 C27 1.375(5) . ? C26 H26 0.9500 . ? C27 C28 1.379(4) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? N3 C29 1.378(4) . ? N3 C50 1.499(4) . ? N3 S2 1.672(2) . ? C29 C30 1.197(4) . ? C30 C31 1.489(4) . ? C31 N4 1.473(3) . ? C31 C37 1.533(4) . ? C31 H31 1.0000 . ? N4 C35 1.455(4) . ? N4 C32 1.470(4) . ? C32 C36 1.512(4) . ? C32 C33 1.537(4) . ? C32 H32 1.0000 . ? C33 C34 1.531(5) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.509(4) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 O4 1.442(4) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? O4 H4A 0.8400 . ? C37 C38 1.383(4) . ? C37 C42 1.392(4) . ? C38 C39 1.385(4) . ? C38 H38 0.9500 . ? C39 C40 1.385(5) . ? C39 H39 0.9500 . ? C40 C41 1.381(4) . ? C40 H40 0.9500 . ? C41 C42 1.383(4) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? S2 O5 1.428(2) . ? S2 O6 1.430(2) . ? S2 C43 1.755(3) . ? C43 C44 1.388(4) . ? C43 C48 1.390(4) . ? C44 C45 1.386(4) . ? C44 H44 0.9500 . ? C45 C46 1.389(4) . ? C45 H45 0.9500 . ? C46 C47 1.394(4) . ? C46 C49 1.506(4) . ? C47 C48 1.383(4) . ? C47 H47 0.9500 . ? C48 H48 0.9500 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 C51 1.511(4) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 C52 1.381(4) . ? C51 C56 1.382(4) . ? C52 C53 1.392(5) . ? C52 H52 0.9500 . ? C53 C54 1.386(4) . ? C53 H53 0.9500 . ? C54 C55 1.382(5) . ? C54 H54 0.9500 . ? C55 C56 1.381(5) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? 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 C2 C3 N2 C7 -59.5(3) . . . . ? C9 C3 N2 C7 67.0(3) . . . . ? C2 C3 N2 C4 64.1(3) . . . . ? C9 C3 N2 C4 -169.5(2) . . . . ? C7 N2 C4 C8 -147.8(3) . . . . ? C3 N2 C4 C8 85.2(3) . . . . ? C7 N2 C4 C5 -26.2(3) . . . . ? C3 N2 C4 C5 -153.2(3) . . . . ? N2 C4 C5 C6 1.5(4) . . . . ? C8 C4 C5 C6 118.7(3) . . . . ? C4 C5 C6 C7 22.6(4) . . . . ? C4 N2 C7 C6 41.3(3) . . . . ? C3 N2 C7 C6 168.8(2) . . . . ? C5 C6 C7 N2 -38.3(3) . . . . ? N2 C4 C8 O1 50.1(4) . . . . ? C5 C4 C8 O1 -64.5(4) . . . . ? C2 C3 C9 C10 -162.6(2) . . . . ? N2 C3 C9 C10 70.8(3) . . . . ? C2 C3 C9 C14 16.7(4) . . . . ? N2 C3 C9 C14 -109.9(3) . . . . ? C14 C9 C10 C11 0.0(4) . . . . ? C3 C9 C10 C11 179.3(3) . . . . ? C9 C10 C11 C12 0.2(5) . . . . ? C10 C11 C12 C13 -0.3(5) . . . . ? C11 C12 C13 C14 0.1(5) . . . . ? C12 C13 C14 C9 0.1(5) . . . . ? C10 C9 C14 C13 -0.1(4) . . . . ? C3 C9 C14 C13 -179.4(3) . . . . ? C1 N1 S1 O2 -36.2(2) . . . . ? C22 N1 S1 O2 179.73(19) . . . . ? C1 N1 S1 O3 -165.10(19) . . . . ? C22 N1 S1 O3 50.8(2) . . . . ? C1 N1 S1 C15 80.1(2) . . . . ? C22 N1 S1 C15 -64.0(2) . . . . ? O2 S1 C15 C20 -159.7(2) . . . . ? O3 S1 C15 C20 -27.0(2) . . . . ? N1 S1 C15 C20 85.8(2) . . . . ? O2 S1 C15 C16 20.5(2) . . . . ? O3 S1 C15 C16 153.3(2) . . . . ? N1 S1 C15 C16 -94.0(2) . . . . ? C20 C15 C16 C17 1.7(4) . . . . ? S1 C15 C16 C17 -178.5(2) . . . . ? C15 C16 C17 C18 -0.4(4) . . . . ? C16 C17 C18 C19 -0.7(4) . . . . ? C16 C17 C18 C21 178.4(3) . . . . ? C17 C18 C19 C20 0.6(4) . . . . ? C21 C18 C19 C20 -178.5(2) . . . . ? C16 C15 C20 C19 -1.8(4) . . . . ? S1 C15 C20 C19 178.4(2) . . . . ? C18 C19 C20 C15 0.7(4) . . . . ? C1 N1 C22 C23 49.6(3) . . . . ? S1 N1 C22 C23 -167.27(19) . . . . ? N1 C22 C23 C24 70.3(3) . . . . ? N1 C22 C23 C28 -113.4(3) . . . . ? C28 C23 C24 C25 2.5(5) . . . . ? C22 C23 C24 C25 178.8(3) . . . . ? C23 C24 C25 C26 -1.6(5) . . . . ? C24 C25 C26 C27 -0.4(5) . . . . ? C25 C26 C27 C28 1.5(5) . . . . ? C26 C27 C28 C23 -0.5(5) . . . . ? C24 C23 C28 C27 -1.4(5) . . . . ? C22 C23 C28 C27 -177.9(3) . . . . ? C30 C31 N4 C35 -51.4(3) . . . . ? C37 C31 N4 C35 74.2(3) . . . . ? C30 C31 N4 C32 72.2(3) . . . . ? C37 C31 N4 C32 -162.2(2) . . . . ? C35 N4 C32 C36 -154.9(2) . . . . ? C31 N4 C32 C36 76.5(3) . . . . ? C35 N4 C32 C33 -34.1(3) . . . . ? C31 N4 C32 C33 -162.7(2) . . . . ? N4 C32 C33 C34 9.1(3) . . . . ? C36 C32 C33 C34 132.1(3) . . . . ? C32 C33 C34 C35 17.6(3) . . . . ? C32 N4 C35 C34 45.5(3) . . . . ? C31 N4 C35 C34 173.0(2) . . . . ? C33 C34 C35 N4 -37.9(3) . . . . ? N4 C32 C36 O4 -75.5(3) . . . . ? C33 C32 C36 O4 167.9(3) . . . . ? N4 C31 C37 C38 -170.3(2) . . . . ? C30 C31 C37 C38 -44.0(3) . . . . ? N4 C31 C37 C42 13.5(4) . . . . ? C30 C31 C37 C42 139.8(3) . . . . ? C42 C37 C38 C39 3.5(4) . . . . ? C31 C37 C38 C39 -172.9(3) . . . . ? C37 C38 C39 C40 -2.3(5) . . . . ? C38 C39 C40 C41 0.3(5) . . . . ? C39 C40 C41 C42 0.4(4) . . . . ? C40 C41 C42 C37 0.9(4) . . . . ? C38 C37 C42 C41 -2.8(4) . . . . ? C31 C37 C42 C41 173.4(3) . . . . ? C29 N3 S2 O5 44.9(2) . . . . ? C50 N3 S2 O5 -176.43(19) . . . . ? C29 N3 S2 O6 174.3(2) . . . . ? C50 N3 S2 O6 -47.0(2) . . . . ? C29 N3 S2 C43 -70.4(2) . . . . ? C50 N3 S2 C43 68.3(2) . . . . ? O5 S2 C43 C44 -20.5(3) . . . . ? O6 S2 C43 C44 -153.2(2) . . . . ? N3 S2 C43 C44 93.7(2) . . . . ? O5 S2 C43 C48 161.9(2) . . . . ? O6 S2 C43 C48 29.2(3) . . . . ? N3 S2 C43 C48 -83.9(2) . . . . ? C48 C43 C44 C45 -0.8(4) . . . . ? S2 C43 C44 C45 -178.3(2) . . . . ? C43 C44 C45 C46 0.1(4) . . . . ? C44 C45 C46 C47 0.5(4) . . . . ? C44 C45 C46 C49 179.8(3) . . . . ? C45 C46 C47 C48 -0.6(4) . . . . ? C49 C46 C47 C48 -179.9(3) . . . . ? C46 C47 C48 C43 0.0(4) . . . . ? C44 C43 C48 C47 0.7(4) . . . . ? S2 C43 C48 C47 178.2(2) . . . . ? C29 N3 C50 C51 -53.5(3) . . . . ? S2 N3 C50 C51 167.32(19) . . . . ? N3 C50 C51 C52 107.6(3) . . . . ? N3 C50 C51 C56 -75.0(3) . . . . ? C56 C51 C52 C53 1.0(4) . . . . ? C50 C51 C52 C53 178.4(3) . . . . ? C51 C52 C53 C54 0.3(5) . . . . ? C52 C53 C54 C55 -1.5(5) . . . . ? C53 C54 C55 C56 1.4(5) . . . . ? C54 C55 C56 C51 -0.1(5) . . . . ? C52 C51 C56 C55 -1.1(5) . . . . ? C50 C51 C56 C55 -178.5(3) . . . . ?