#------------------------------------------------------------------------------ #$Date: 2024-10-15 03:42:13 +0300 (Tue, 15 Oct 2024) $ #$Revision: 295488 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160183.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_7160183 loop_ _publ_author_name 'Fesenko, Anastasia' 'Grigoriev, Mikhail S.' 'Shutalev, Anatoly' _publ_section_title ; Effective self-assembly of 21- and 14-membered azamacrocycles via condition-controlled cyclotrimerization or cyclodimerization of different thiosemicarbazide-based precursors ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01384K _journal_year 2024 _chemical_formula_sum 'C21 H40 N10 O S3' _chemical_formula_weight 544.81 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2024-06-10 deposited with the CCDC. 2024-10-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.928(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.8167(4) _cell_length_b 11.8970(4) _cell_length_c 18.1261(6) _cell_measurement_reflns_used 9841 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 25.06 _cell_measurement_theta_min 3.18 _cell_volume 2763.51(16) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker KAPPA APEX II area-detector diffractometer' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1133 _diffrn_reflns_av_unetI/netI 0.0616 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 100195 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.999 _diffrn_reflns_theta_min 3.425 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_T_max 0.959 _exptl_absorpt_correction_T_min 0.917 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.309 _exptl_crystal_description fragment _exptl_crystal_F_000 1168 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.531 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.072 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 357 _refine_ls_number_reflns 8049 _refine_ls_number_restraints 7 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0490 _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^)+(0.0302P)^2^+2.0086P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0867 _refine_ls_wR_factor_ref 0.0980 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5621 _reflns_number_total 8049 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01384k2.cif _cod_data_source_block L4132_LT _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7160183 _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 0.948 _shelx_estimated_absorpt_t_max 0.959 _shelx_res_file ; TITL L4132.res in P2(1)/n L4132.res created by SHELXL-2018/3 at 21:12:07 on 23-Sep-2021 CELL 0.71073 12.8167 11.8970 18.1261 90.000 90.928 90.000 ZERR 4.000 0.0004 0.0004 0.0006 0.000 0.001 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N S O UNIT 84 160 40 12 4 TEMP -173 SIZE 0.18 0.16 0.14 L.S. 10 SADI 0.01 N3 C28 N3 C28A SADI 0.01 N3 C29 N3 C29A SADI 0.01 N3 C30 N3 C30A SADI 0.01 O1 C28 O1 C28A SADI 0.01 C28 C29 C28A C29A SADI 0.01 C28 C30 C28A C30A SADI 0.01 C30 C29 C30A C29A BOND $H FMAP 2 PLAN 20 HTAB HTAB N2 O1 HTAB N4 N1 HTAB N11 S1 HTAB N11 N8 EQIV $1 -x, -y+2, -z+1 HTAB N18 O1 HTAB C12 S2 HTAB C20 O1 EQIV $2 -x, -y+1, -z+1 HTAB C23 N8_$2 HTAB C23 N15_$2 EQIV $3 -x+1/2, y+1/2, -z+3/2 HTAB C25 S1_$3 ACTA CONF SHEL 6 0.5 OMIT -2 60 WGHT 0.030200 2.008600 FVAR 0.50358 0.87050 S2 4 -0.102512 0.640424 0.697644 11.00000 0.01267 0.01634 = 0.01956 -0.00712 0.00343 0.00135 S1 4 0.343346 0.476849 0.623404 11.00000 0.01862 0.01729 = 0.01488 0.00163 -0.00134 -0.00291 S3 4 0.118512 0.970440 0.412042 11.00000 0.01818 0.01863 = 0.01432 0.00339 0.00093 0.00365 O1 5 0.448616 0.757978 0.564477 11.00000 0.01882 0.02382 = 0.01933 0.00180 -0.00002 -0.00144 N1 3 0.292405 0.570716 0.419108 11.00000 0.01841 0.01267 = 0.01348 -0.00032 0.00329 0.00034 N2 3 0.329813 0.569429 0.491048 11.00000 0.01914 0.01100 = 0.01358 0.00010 0.00159 -0.00429 H2 2 0.365231 0.623057 0.511569 11.00000 -1.20000 N3 3 0.510025 0.725268 0.681554 11.00000 0.02166 0.02712 = 0.02155 -0.00020 -0.00589 -0.00378 N4 3 0.252753 0.397428 0.499682 11.00000 0.01713 0.00943 = 0.01121 0.00071 0.00242 -0.00038 H4 2 0.242442 0.405465 0.454292 11.00000 -1.20000 N8 3 0.056849 0.412569 0.591969 11.00000 0.01325 0.01086 = 0.01390 -0.00300 0.00366 0.00109 N9 3 -0.022068 0.481887 0.616937 11.00000 0.00900 0.01329 = 0.01649 -0.00570 0.00094 0.00001 H9 2 -0.085615 0.470353 0.606527 11.00000 -1.20000 N11 3 0.099117 0.579069 0.685895 11.00000 0.01265 0.01213 = 0.01285 -0.00487 0.00225 0.00088 H11 2 0.141009 0.536214 0.664827 11.00000 -1.20000 N15 3 0.200071 0.837101 0.600627 11.00000 0.01389 0.00939 = 0.01240 0.00020 -0.00068 0.00051 N16 3 0.153300 0.909438 0.549899 11.00000 0.01280 0.01228 = 0.01363 0.00245 0.00226 0.00365 H16 2 0.091972 0.935003 0.556006 11.00000 -1.20000 N18 3 0.281820 0.858216 0.470291 11.00000 0.01491 0.01489 = 0.01013 0.00266 0.00368 0.00230 H18 2 0.313095 0.835446 0.508586 11.00000 -1.20000 C3 1 0.305906 0.479055 0.533288 11.00000 0.01111 0.01326 = 0.01460 -0.00086 0.00494 0.00114 C5 1 0.223294 0.290080 0.532649 11.00000 0.01508 0.00847 = 0.01551 0.00054 0.00416 0.00081 AFIX 13 H5A 2 0.229963 0.295691 0.587569 11.00000 -1.20000 AFIX 0 C6 1 0.110331 0.264320 0.511460 11.00000 0.01710 0.00900 = 0.01407 -0.00342 0.00320 -0.00068 AFIX 23 H6A 2 0.104318 0.262379 0.456954 11.00000 -1.20000 H6B 2 0.093178 0.188250 0.529789 11.00000 -1.20000 AFIX 0 C7 1 0.030576 0.345175 0.539849 11.00000 0.01386 0.00934 = 0.01248 0.00021 0.00285 -0.00252 C10 1 -0.000788 0.564228 0.666860 11.00000 0.01468 0.00872 = 0.01022 0.00058 0.00140 -0.00068 C12 1 0.137511 0.652713 0.745014 11.00000 0.01412 0.01170 = 0.00954 -0.00267 0.00045 -0.00148 AFIX 13 H12A 2 0.076521 0.688837 0.769258 11.00000 -1.20000 AFIX 0 C13 1 0.209410 0.744851 0.715821 11.00000 0.01189 0.01286 = 0.01086 -0.00001 -0.00021 0.00007 AFIX 23 H13A 2 0.239240 0.786694 0.758401 11.00000 -1.20000 H13B 2 0.268015 0.708662 0.689995 11.00000 -1.20000 AFIX 0 C14 1 0.157987 0.827535 0.664035 11.00000 0.01141 0.00925 = 0.01268 -0.00116 -0.00020 -0.00169 C17 1 0.190601 0.908920 0.479333 11.00000 0.01609 0.00743 = 0.01540 -0.00072 0.00194 -0.00177 C19 1 0.340741 0.858248 0.401443 11.00000 0.01686 0.01316 = 0.01174 0.00098 0.00622 -0.00013 AFIX 13 H19A 2 0.290896 0.870492 0.359193 11.00000 -1.20000 AFIX 0 C20 1 0.394797 0.743660 0.391250 11.00000 0.01507 0.01277 = 0.01454 0.00066 0.00600 -0.00077 AFIX 23 H20A 2 0.444718 0.749845 0.350337 11.00000 -1.20000 H20B 2 0.435296 0.725745 0.436713 11.00000 -1.20000 AFIX 0 C21 1 0.321162 0.648599 0.374985 11.00000 0.01521 0.01070 = 0.01571 0.00010 0.00615 0.00121 C22 1 0.295823 0.197979 0.505187 11.00000 0.01903 0.01372 = 0.02245 -0.00078 0.00473 0.00291 AFIX 137 H22A 2 0.368070 0.216616 0.518840 11.00000 -1.50000 H22B 2 0.289242 0.192044 0.451388 11.00000 -1.50000 H22C 2 0.276748 0.126115 0.527694 11.00000 -1.50000 AFIX 0 C23 1 -0.076091 0.340111 0.505279 11.00000 0.01484 0.01406 = 0.01927 -0.00379 0.00000 -0.00324 AFIX 137 H23A 2 -0.100219 0.416454 0.493987 11.00000 -1.50000 H23B 2 -0.124315 0.304468 0.539561 11.00000 -1.50000 H23C 2 -0.073622 0.296094 0.459641 11.00000 -1.50000 AFIX 0 C24 1 0.196398 0.581604 0.801914 11.00000 0.02652 0.01538 = 0.01651 0.00284 -0.00316 -0.00203 AFIX 137 H24A 2 0.148999 0.525717 0.822692 11.00000 -1.50000 H24B 2 0.223480 0.630178 0.841468 11.00000 -1.50000 H24C 2 0.254572 0.543203 0.778161 11.00000 -1.50000 AFIX 0 C25 1 0.064468 0.891501 0.689760 11.00000 0.01532 0.01425 = 0.01470 0.00049 0.00200 0.00290 AFIX 137 H25A 2 0.069391 0.969855 0.673501 11.00000 -1.50000 H25B 2 0.061995 0.888922 0.743743 11.00000 -1.50000 H25C 2 0.000937 0.857505 0.668839 11.00000 -1.50000 AFIX 0 C26 1 0.420713 0.952932 0.402099 11.00000 0.02854 0.01520 = 0.02843 -0.00424 0.01514 -0.00580 AFIX 137 H26A 2 0.385365 1.024750 0.410447 11.00000 -1.50000 H26B 2 0.456010 0.955158 0.354564 11.00000 -1.50000 H26C 2 0.472227 0.939818 0.441710 11.00000 -1.50000 AFIX 0 C27 1 0.277014 0.640644 0.297888 11.00000 0.02664 0.01964 = 0.01638 0.00204 0.00254 -0.00561 AFIX 137 H27A 2 0.227071 0.578363 0.294992 11.00000 -1.50000 H27B 2 0.333682 0.627285 0.263308 11.00000 -1.50000 H27C 2 0.241485 0.711092 0.285065 11.00000 -1.50000 AFIX 0 PART 1 C28 1 0.450184 0.779522 0.631231 21.00000 0.01259 0.01376 = 0.02484 -0.00227 0.00241 -0.00226 AFIX 43 H28A 2 0.406309 0.838178 0.648124 21.00000 -1.20000 AFIX 0 C29 1 0.578373 0.636723 0.663946 21.00000 0.01708 0.02640 = 0.03272 -0.00185 0.00159 0.00578 AFIX 137 H29A 2 0.571341 0.619018 0.611298 21.00000 -1.50000 H29B 2 0.560897 0.570165 0.693107 21.00000 -1.50000 H29C 2 0.650385 0.659442 0.675195 21.00000 -1.50000 AFIX 0 C30 1 0.495897 0.753911 0.760341 21.00000 0.02518 0.05372 = 0.02138 -0.01408 -0.00245 0.00342 AFIX 137 H30A 2 0.447114 0.816986 0.764226 21.00000 -1.50000 H30B 2 0.563328 0.775065 0.782504 21.00000 -1.50000 H30C 2 0.467906 0.688622 0.786386 21.00000 -1.50000 AFIX 0 PART 2 C28A 1 0.496001 0.695960 0.606920 -21.00000 0.02836 AFIX 43 H28B 2 0.523713 0.627114 0.589317 -21.00000 -1.20000 AFIX 0 C29A 1 0.500258 0.825814 0.712013 -21.00000 0.03471 AFIX 137 H29D 2 0.481591 0.817312 0.763932 -21.00000 -1.50000 H29E 2 0.445433 0.868055 0.685850 -21.00000 -1.50000 H29F 2 0.566522 0.866484 0.708799 -21.00000 -1.50000 AFIX 0 C30A 1 0.589220 0.639271 0.714936 -21.00000 0.03033 AFIX 137 H30D 2 0.567272 0.617715 0.764506 -21.00000 -1.50000 H30E 2 0.658679 0.673581 0.717865 -21.00000 -1.50000 H30F 2 0.591568 0.572380 0.683454 -21.00000 -1.50000 PART 0 AFIX 0 HKLF 4 REM L4132.res in P2(1)/n REM wR2 = 0.0980, GooF = S = 1.041, Restrained GooF = 1.053 for all data REM R1 = 0.0490 for 5621 Fo > 4sig(Fo) and 0.0866 for all 8049 data REM 357 parameters refined using 7 restraints END WGHT 0.0302 2.0093 REM Instructions for potential hydrogen bonds HTAB N2 O1 HTAB N4 N1 HTAB N11 S1 HTAB N11 N8 HTAB N16 S3_$1 HTAB N18 O1 HTAB C12 S2 HTAB C20 O1 HTAB C23 N8_$2 HTAB C23 N15_$2 HTAB C23 N16_$2 HTAB C25 S1_$3 HTAB C25 S2 EQIV $4 x+1/2, -y+3/2, z+1/2 HTAB C30A S3_$4 REM Highest difference peak 0.531, deepest hole -0.428, 1-sigma level 0.072 Q1 1 0.5001 0.7954 0.7128 11.00000 0.05 0.53 Q2 1 0.3647 0.8045 0.4020 11.00000 0.05 0.38 Q3 1 0.5446 0.6822 0.6683 11.00000 0.05 0.38 Q4 1 0.5002 0.6827 0.5869 11.00000 0.05 0.37 Q5 1 0.4988 0.7622 0.6646 11.00000 0.05 0.35 Q6 1 0.0627 0.9936 0.4388 11.00000 0.05 0.34 Q7 1 0.0770 0.3094 0.5236 11.00000 0.05 0.34 Q8 1 0.6002 0.6049 0.7128 11.00000 0.05 0.34 Q9 1 0.0805 0.4350 0.5587 11.00000 0.05 0.34 Q10 1 0.1960 0.8018 0.6895 11.00000 0.05 0.34 Q11 1 0.1791 0.6898 0.7318 11.00000 0.05 0.33 Q12 1 0.3127 0.5218 0.5131 11.00000 0.05 0.32 Q13 1 -0.0461 0.5844 0.6914 11.00000 0.05 0.31 Q14 1 0.5167 0.7396 0.7060 11.00000 0.05 0.31 Q15 1 0.2012 0.8548 0.6428 11.00000 0.05 0.30 Q16 1 0.1930 0.9549 0.4413 11.00000 0.05 0.30 Q17 1 0.2947 0.6507 0.3362 11.00000 0.05 0.30 Q18 1 0.1621 0.2758 0.5189 11.00000 0.05 0.30 Q19 1 -0.0196 0.3443 0.5199 11.00000 0.05 0.29 Q20 1 0.3198 0.8622 0.4373 11.00000 0.05 0.29 ; _shelx_res_checksum 57971 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 S2 S -0.10251(4) 0.64042(4) 0.69764(3) 0.01615(11) Uani 1 1 d . . . . . S1 S 0.34335(4) 0.47685(4) 0.62340(3) 0.01695(11) Uani 1 1 d . . . . . S3 S 0.11851(4) 0.97044(4) 0.41204(3) 0.01704(11) Uani 1 1 d . . . . . O1 O 0.44862(10) 0.75798(12) 0.56448(8) 0.0207(3) Uani 1 1 d D . . . . N1 N 0.29241(12) 0.57072(13) 0.41911(8) 0.0148(3) Uani 1 1 d . . . . . N2 N 0.32981(13) 0.56943(14) 0.49105(9) 0.0146(3) Uani 1 1 d . . . . . H2 H 0.3652(17) 0.6231(19) 0.5116(12) 0.017 Uiso 1 1 d . U . . . N3 N 0.51003(13) 0.72527(15) 0.68155(10) 0.0235(4) Uani 1 1 d D . . . . N4 N 0.25275(12) 0.39743(13) 0.49968(9) 0.0126(3) Uani 1 1 d . . . . . H4 H 0.2424(16) 0.4055(18) 0.4543(12) 0.015 Uiso 1 1 d . U . . . N8 N 0.05685(12) 0.41257(13) 0.59197(8) 0.0126(3) Uani 1 1 d . . . . . N9 N -0.02207(12) 0.48189(13) 0.61694(9) 0.0129(3) Uani 1 1 d . . . . . H9 H -0.0856(17) 0.4704(18) 0.6065(11) 0.016 Uiso 1 1 d . U . . . N11 N 0.09912(12) 0.57907(13) 0.68589(8) 0.0125(3) Uani 1 1 d . . . . . H11 H 0.1410(16) 0.5362(18) 0.6648(11) 0.015 Uiso 1 1 d . U . . . N15 N 0.20007(11) 0.83710(12) 0.60063(8) 0.0119(3) Uani 1 1 d . . . . . N16 N 0.15330(12) 0.90944(13) 0.54990(8) 0.0129(3) Uani 1 1 d . . . . . H16 H 0.0920(17) 0.9350(18) 0.5560(11) 0.015 Uiso 1 1 d . U . . . N18 N 0.28182(12) 0.85822(13) 0.47029(9) 0.0133(3) Uani 1 1 d . . . . . H18 H 0.3131(16) 0.8354(18) 0.5086(12) 0.016 Uiso 1 1 d . U . . . C3 C 0.30591(13) 0.47906(16) 0.53329(10) 0.0129(4) Uani 1 1 d . . . . . C5 C 0.22329(14) 0.29008(15) 0.53265(10) 0.0130(4) Uani 1 1 d . . . . . H5A H 0.229963 0.295691 0.587569 0.016 Uiso 1 1 calc R U . . . C6 C 0.11033(14) 0.26432(15) 0.51146(10) 0.0134(4) Uani 1 1 d . . . . . H6A H 0.104318 0.262379 0.456954 0.016 Uiso 1 1 calc R U . . . H6B H 0.093178 0.188250 0.529789 0.016 Uiso 1 1 calc R U . . . C7 C 0.03058(14) 0.34518(15) 0.53985(10) 0.0119(3) Uani 1 1 d . . . . . C10 C -0.00079(14) 0.56423(15) 0.66686(10) 0.0112(3) Uani 1 1 d . . . . . C12 C 0.13751(14) 0.65271(15) 0.74501(9) 0.0118(3) Uani 1 1 d . . . . . H12A H 0.076521 0.688837 0.769258 0.014 Uiso 1 1 calc R U . . . C13 C 0.20941(14) 0.74485(15) 0.71582(10) 0.0119(3) Uani 1 1 d . . . . . H13A H 0.239240 0.786694 0.758401 0.014 Uiso 1 1 calc R U . . . H13B H 0.268015 0.708662 0.689995 0.014 Uiso 1 1 calc R U . . . C14 C 0.15799(13) 0.82754(15) 0.66403(10) 0.0111(3) Uani 1 1 d . . . . . C17 C 0.19060(14) 0.90892(15) 0.47933(10) 0.0130(4) Uani 1 1 d . . . . . C19 C 0.34074(14) 0.85825(16) 0.40144(10) 0.0139(4) Uani 1 1 d . . . . . H19A H 0.290896 0.870492 0.359193 0.017 Uiso 1 1 calc R U . . . C20 C 0.39480(14) 0.74366(15) 0.39125(11) 0.0141(4) Uani 1 1 d . . . . . H20A H 0.444718 0.749845 0.350337 0.017 Uiso 1 1 calc R U . . . H20B H 0.435296 0.725745 0.436713 0.017 Uiso 1 1 calc R U . . . C21 C 0.32116(14) 0.64860(15) 0.37498(10) 0.0138(4) Uani 1 1 d . . . . . C22 C 0.29582(15) 0.19798(16) 0.50519(11) 0.0184(4) Uani 1 1 d . . . . . H22A H 0.368070 0.216616 0.518840 0.028 Uiso 1 1 calc R U . . . H22B H 0.289242 0.192044 0.451388 0.028 Uiso 1 1 calc R U . . . H22C H 0.276748 0.126115 0.527694 0.028 Uiso 1 1 calc R U . . . C23 C -0.07609(14) 0.34011(16) 0.50528(11) 0.0161(4) Uani 1 1 d . . . . . H23A H -0.100219 0.416454 0.493987 0.024 Uiso 1 1 calc R U . . . H23B H -0.124315 0.304468 0.539561 0.024 Uiso 1 1 calc R U . . . H23C H -0.073622 0.296094 0.459641 0.024 Uiso 1 1 calc R U . . . C24 C 0.19640(16) 0.58160(17) 0.80191(11) 0.0195(4) Uani 1 1 d . . . . . H24A H 0.148999 0.525717 0.822692 0.029 Uiso 1 1 calc R U . . . H24B H 0.223480 0.630178 0.841468 0.029 Uiso 1 1 calc R U . . . H24C H 0.254572 0.543203 0.778161 0.029 Uiso 1 1 calc R U . . . C25 C 0.06447(14) 0.89150(16) 0.68976(10) 0.0147(4) Uani 1 1 d . . . . . H25A H 0.069391 0.969855 0.673501 0.022 Uiso 1 1 calc R U . . . H25B H 0.061995 0.888922 0.743743 0.022 Uiso 1 1 calc R U . . . H25C H 0.000937 0.857505 0.668839 0.022 Uiso 1 1 calc R U . . . C26 C 0.42071(17) 0.95293(17) 0.40210(12) 0.0239(5) Uani 1 1 d . . . . . H26A H 0.385365 1.024750 0.410447 0.036 Uiso 1 1 calc R U . . . H26B H 0.456010 0.955158 0.354564 0.036 Uiso 1 1 calc R U . . . H26C H 0.472227 0.939818 0.441710 0.036 Uiso 1 1 calc R U . . . C27 C 0.27701(16) 0.64064(18) 0.29789(11) 0.0209(4) Uani 1 1 d . . . . . H27A H 0.227071 0.578363 0.294992 0.031 Uiso 1 1 calc R U . . . H27B H 0.333682 0.627285 0.263308 0.031 Uiso 1 1 calc R U . . . H27C H 0.241485 0.711092 0.285065 0.031 Uiso 1 1 calc R U . . . C28 C 0.45018(16) 0.77952(18) 0.63123(13) 0.0170(5) Uani 0.870(4) 1 d D . P A 1 H28A H 0.406309 0.838178 0.648124 0.020 Uiso 0.870(4) 1 calc R U P A 1 C29 C 0.57837(18) 0.6367(2) 0.66395(15) 0.0254(6) Uani 0.870(4) 1 d D . P A 1 H29A H 0.571341 0.619018 0.611298 0.038 Uiso 0.870(4) 1 calc R U P A 1 H29B H 0.560897 0.570165 0.693107 0.038 Uiso 0.870(4) 1 calc R U P A 1 H29C H 0.650385 0.659442 0.675195 0.038 Uiso 0.870(4) 1 calc R U P A 1 C30 C 0.4959(2) 0.7539(3) 0.76034(14) 0.0335(7) Uani 0.870(4) 1 d D . P A 1 H30A H 0.447114 0.816986 0.764226 0.050 Uiso 0.870(4) 1 calc R U P A 1 H30B H 0.563328 0.775065 0.782504 0.050 Uiso 0.870(4) 1 calc R U P A 1 H30C H 0.467906 0.688622 0.786386 0.050 Uiso 0.870(4) 1 calc R U P A 1 C28A C 0.4960(12) 0.6960(10) 0.6069(5) 0.028(4) Uiso 0.130(4) 1 d D . P A 2 H28B H 0.523713 0.627114 0.589317 0.034 Uiso 0.130(4) 1 calc R U P A 2 C29A C 0.5003(14) 0.8258(9) 0.7120(8) 0.035(5) Uiso 0.130(4) 1 d D . P A 2 H29D H 0.481591 0.817312 0.763932 0.052 Uiso 0.130(4) 1 calc R U P A 2 H29E H 0.445433 0.868055 0.685850 0.052 Uiso 0.130(4) 1 calc R U P A 2 H29F H 0.566522 0.866484 0.708799 0.052 Uiso 0.130(4) 1 calc R U P A 2 C30A C 0.5892(12) 0.6393(11) 0.7149(8) 0.030(4) Uiso 0.130(4) 1 d D . P A 2 H30D H 0.567272 0.617715 0.764506 0.045 Uiso 0.130(4) 1 calc R U P A 2 H30E H 0.658679 0.673581 0.717865 0.045 Uiso 0.130(4) 1 calc R U P A 2 H30F H 0.591568 0.572380 0.683454 0.045 Uiso 0.130(4) 1 calc R U P A 2 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 S2 0.0127(2) 0.0163(2) 0.0196(2) -0.00712(19) 0.00343(18) 0.00135(18) S1 0.0186(2) 0.0173(2) 0.0149(2) 0.00163(19) -0.00134(18) -0.00291(19) S3 0.0182(2) 0.0186(2) 0.0143(2) 0.00339(19) 0.00093(18) 0.00365(19) O1 0.0188(7) 0.0238(8) 0.0193(7) 0.0018(6) 0.0000(6) -0.0014(6) N1 0.0184(8) 0.0127(8) 0.0135(8) -0.0003(6) 0.0033(6) 0.0003(6) N2 0.0191(8) 0.0110(8) 0.0136(8) 0.0001(6) 0.0016(6) -0.0043(6) N3 0.0217(9) 0.0271(10) 0.0215(9) -0.0002(8) -0.0059(7) -0.0038(7) N4 0.0171(8) 0.0094(7) 0.0112(7) 0.0007(6) 0.0024(6) -0.0004(6) N8 0.0133(7) 0.0109(7) 0.0139(8) -0.0030(6) 0.0037(6) 0.0011(6) N9 0.0090(7) 0.0133(8) 0.0165(8) -0.0057(6) 0.0009(6) 0.0000(6) N11 0.0126(7) 0.0121(8) 0.0128(8) -0.0049(6) 0.0023(6) 0.0009(6) N15 0.0139(7) 0.0094(7) 0.0124(7) 0.0002(6) -0.0007(6) 0.0005(6) N16 0.0128(7) 0.0123(8) 0.0136(8) 0.0024(6) 0.0023(6) 0.0037(6) N18 0.0149(8) 0.0149(8) 0.0101(7) 0.0027(6) 0.0037(6) 0.0023(6) C3 0.0111(8) 0.0133(9) 0.0146(9) -0.0009(7) 0.0049(7) 0.0011(7) C5 0.0151(9) 0.0085(8) 0.0155(9) 0.0005(7) 0.0042(7) 0.0008(7) C6 0.0171(9) 0.0090(8) 0.0141(9) -0.0034(7) 0.0032(7) -0.0007(7) C7 0.0139(8) 0.0093(8) 0.0125(9) 0.0002(7) 0.0028(7) -0.0025(7) C10 0.0147(8) 0.0087(8) 0.0102(8) 0.0006(7) 0.0014(7) -0.0007(7) C12 0.0141(8) 0.0117(8) 0.0095(8) -0.0027(7) 0.0004(7) -0.0015(7) C13 0.0119(8) 0.0129(9) 0.0109(9) 0.0000(7) -0.0002(7) 0.0001(7) C14 0.0114(8) 0.0092(8) 0.0127(8) -0.0012(7) -0.0002(7) -0.0017(6) C17 0.0161(9) 0.0074(8) 0.0154(9) -0.0007(7) 0.0019(7) -0.0018(7) C19 0.0169(9) 0.0132(9) 0.0117(9) 0.0010(7) 0.0062(7) -0.0001(7) C20 0.0151(9) 0.0128(9) 0.0145(9) 0.0007(7) 0.0060(7) -0.0008(7) C21 0.0152(9) 0.0107(9) 0.0157(9) 0.0001(7) 0.0062(7) 0.0012(7) C22 0.0190(10) 0.0137(9) 0.0225(10) -0.0008(8) 0.0047(8) 0.0029(8) C23 0.0148(9) 0.0141(9) 0.0193(10) -0.0038(8) 0.0000(7) -0.0032(7) C24 0.0265(11) 0.0154(10) 0.0165(10) 0.0028(8) -0.0032(8) -0.0020(8) C25 0.0153(9) 0.0142(9) 0.0147(9) 0.0005(7) 0.0020(7) 0.0029(7) C26 0.0285(11) 0.0152(10) 0.0284(12) -0.0042(8) 0.0151(9) -0.0058(8) C27 0.0266(10) 0.0196(10) 0.0164(10) 0.0020(8) 0.0025(8) -0.0056(9) C28 0.0126(10) 0.0138(11) 0.0248(13) -0.0023(9) 0.0024(9) -0.0023(8) C29 0.0171(11) 0.0264(13) 0.0327(15) -0.0018(11) 0.0016(10) 0.0058(10) C30 0.0252(13) 0.0537(19) 0.0214(14) -0.0141(13) -0.0024(11) 0.0034(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C21 N1 N2 119.85(16) . . ? C3 N2 N1 117.57(16) . . ? C3 N2 H2 117.6(14) . . ? N1 N2 H2 124.7(14) . . ? C29A N3 C28A 127.9(7) . . ? C28 N3 C29 123.63(19) . . ? C28 N3 C30 117.72(19) . . ? C29 N3 C30 118.4(2) . . ? C29A N3 C30A 119.8(7) . . ? C28A N3 C30A 106.5(6) . . ? C3 N4 C5 125.80(16) . . ? C3 N4 H4 116.0(15) . . ? C5 N4 H4 117.6(15) . . ? C7 N8 N9 115.39(15) . . ? C10 N9 N8 120.45(15) . . ? C10 N9 H9 116.7(14) . . ? N8 N9 H9 122.4(15) . . ? C10 N11 C12 125.40(15) . . ? C10 N11 H11 115.0(14) . . ? C12 N11 H11 119.2(14) . . ? C14 N15 N16 117.72(15) . . ? C17 N16 N15 117.46(15) . . ? C17 N16 H16 117.3(14) . . ? N15 N16 H16 121.7(14) . . ? C17 N18 C19 124.78(16) . . ? C17 N18 H18 117.0(14) . . ? C19 N18 H18 117.2(14) . . ? N4 C3 N2 116.04(16) . . ? N4 C3 S1 124.44(14) . . ? N2 C3 S1 119.51(14) . . ? N4 C5 C6 108.87(15) . . ? N4 C5 C22 109.34(15) . . ? C6 C5 C22 110.79(15) . . ? N4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C22 C5 H5A 109.3 . . ? C7 C6 C5 115.76(15) . . ? C7 C6 H6A 108.3 . . ? C5 C6 H6A 108.3 . . ? C7 C6 H6B 108.3 . . ? C5 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? N8 C7 C23 124.20(16) . . ? N8 C7 C6 118.82(16) . . ? C23 C7 C6 116.97(15) . . ? N11 C10 N9 116.73(16) . . ? N11 C10 S2 125.92(14) . . ? N9 C10 S2 117.33(13) . . ? N11 C12 C24 108.67(15) . . ? N11 C12 C13 111.87(14) . . ? C24 C12 C13 109.68(15) . . ? N11 C12 H12A 108.9 . . ? C24 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C14 C13 C12 115.06(15) . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13A 108.5 . . ? C14 C13 H13B 108.5 . . ? C12 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? N15 C14 C25 125.67(16) . . ? N15 C14 C13 115.52(16) . . ? C25 C14 C13 118.81(15) . . ? N18 C17 N16 115.95(16) . . ? N18 C17 S3 125.54(14) . . ? N16 C17 S3 118.51(14) . . ? N18 C19 C26 110.41(15) . . ? N18 C19 C20 109.86(15) . . ? C26 C19 C20 110.57(15) . . ? N18 C19 H19A 108.6 . . ? C26 C19 H19A 108.7 . . ? C20 C19 H19A 108.6 . . ? C21 C20 C19 114.08(15) . . ? C21 C20 H20A 108.7 . . ? C19 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C19 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? N1 C21 C20 127.51(18) . . ? N1 C21 C27 115.28(17) . . ? C20 C21 C27 117.19(16) . . ? C5 C22 H22A 109.5 . . ? C5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C7 C23 H23A 109.5 . . ? C7 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C7 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C12 C24 H24A 109.5 . . ? C12 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C12 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C14 C25 H25A 109.5 . . ? C14 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C14 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C19 C26 H26A 109.5 . . ? C19 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C19 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C21 C27 H27A 109.5 . . ? C21 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C21 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O1 C28 N3 124.3(2) . . ? O1 C28 H28A 117.9 . . ? N3 C28 H28A 117.9 . . ? N3 C29 H29A 109.5 . . ? N3 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N3 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N3 C30 H30A 109.5 . . ? N3 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N3 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O1 C28A N3 120.7(8) . . ? O1 C28A H28B 119.6 . . ? N3 C28A H28B 119.6 . . ? N3 C29A H29D 109.5 . . ? N3 C29A H29E 109.5 . . ? H29D C29A H29E 109.5 . . ? N3 C29A H29F 109.5 . . ? H29D C29A H29F 109.5 . . ? H29E C29A H29F 109.5 . . ? N3 C30A H30D 109.5 . . ? N3 C30A H30E 109.5 . . ? H30D C30A H30E 109.5 . . ? N3 C30A H30F 109.5 . . ? H30D C30A H30F 109.5 . . ? H30E C30A H30F 109.5 . . ? 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 S2 C10 1.6901(18) . ? S1 C3 1.6952(19) . ? S3 C17 1.6854(19) . ? O1 C28A 1.221(8) . ? O1 C28 1.237(3) . ? N1 C21 1.282(2) . ? N1 N2 1.382(2) . ? N2 C3 1.358(2) . ? N2 H2 0.86(2) . ? N3 C29A 1.324(8) . ? N3 C28 1.347(3) . ? N3 C28A 1.406(8) . ? N3 C29 1.410(3) . ? N3 C30 1.482(3) . ? N3 C30A 1.557(8) . ? N4 C3 1.328(2) . ? N4 C5 1.462(2) . ? N4 H4 0.84(2) . ? N8 C7 1.280(2) . ? N8 N9 1.387(2) . ? N9 C10 1.358(2) . ? N9 H9 0.84(2) . ? N11 C10 1.332(2) . ? N11 C12 1.463(2) . ? N11 H11 0.84(2) . ? N15 C14 1.283(2) . ? N15 N16 1.388(2) . ? N16 C17 1.373(2) . ? N16 H16 0.85(2) . ? N18 C17 1.328(2) . ? N18 C19 1.469(2) . ? N18 H18 0.84(2) . ? C5 C6 1.523(3) . ? C5 C22 1.526(3) . ? C5 H5A 1.0000 . ? C6 C7 1.501(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C23 1.496(2) . ? C12 C24 1.524(3) . ? C12 C13 1.532(2) . ? C12 H12A 1.0000 . ? C13 C14 1.504(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C25 1.500(2) . ? C19 C26 1.523(3) . ? C19 C20 1.542(3) . ? C19 H19A 1.0000 . ? C20 C21 1.499(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C27 1.502(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9500 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C28A H28B 0.9500 . ? C29A H29D 0.9800 . ? C29A H29E 0.9800 . ? C29A H29F 0.9800 . ? C30A H30D 0.9800 . ? C30A H30E 0.9800 . ? C30A H30F 0.9800 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N2 H2 O1 0.86(2) 2.15(2) 3.009(2) 178(2) . yes N4 H4 N1 0.84(2) 2.17(2) 2.582(2) 110.5(18) . yes N11 H11 S1 0.84(2) 2.80(2) 3.5602(16) 151.5(18) . yes N11 H11 N8 0.84(2) 2.24(2) 2.662(2) 111.2(17) . yes N18 H18 O1 0.84(2) 2.20(2) 2.965(2) 151.4(19) . yes C12 H12A S2 1.00 2.68 3.1838(18) 111.3 . yes C20 H20B O1 0.99 2.35 3.208(2) 144.5 . yes C23 H23A N8 0.98 2.63 3.441(2) 140.6 3_566 yes C23 H23C N15 0.98 2.50 3.249(2) 132.6 3_566 yes C25 H25B S1 0.98 2.88 3.710(2) 143.6 2_556 yes 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 C21 N1 N2 C3 -173.23(16) . . . . ? C7 N8 N9 C10 -173.46(16) . . . . ? C14 N15 N16 C17 -172.05(16) . . . . ? C5 N4 C3 N2 176.52(16) . . . . ? C5 N4 C3 S1 -4.0(3) . . . . ? N1 N2 C3 N4 3.3(2) . . . . ? N1 N2 C3 S1 -176.21(12) . . . . ? C3 N4 C5 C6 135.98(18) . . . . ? C3 N4 C5 C22 -102.9(2) . . . . ? N4 C5 C6 C7 -63.6(2) . . . . ? C22 C5 C6 C7 176.09(16) . . . . ? N9 N8 C7 C23 1.3(3) . . . . ? N9 N8 C7 C6 -177.82(15) . . . . ? C5 C6 C7 N8 -15.8(2) . . . . ? C5 C6 C7 C23 164.99(16) . . . . ? C12 N11 C10 N9 -171.89(16) . . . . ? C12 N11 C10 S2 9.7(3) . . . . ? N8 N9 C10 N11 4.5(2) . . . . ? N8 N9 C10 S2 -176.90(13) . . . . ? C10 N11 C12 C24 119.42(19) . . . . ? C10 N11 C12 C13 -119.33(19) . . . . ? N11 C12 C13 C14 64.5(2) . . . . ? C24 C12 C13 C14 -174.84(15) . . . . ? N16 N15 C14 C25 -2.7(3) . . . . ? N16 N15 C14 C13 177.78(15) . . . . ? C12 C13 C14 N15 -123.79(17) . . . . ? C12 C13 C14 C25 56.6(2) . . . . ? C19 N18 C17 N16 -173.28(16) . . . . ? C19 N18 C17 S3 7.2(3) . . . . ? N15 N16 C17 N18 -14.3(2) . . . . ? N15 N16 C17 S3 165.28(12) . . . . ? C17 N18 C19 C26 94.3(2) . . . . ? C17 N18 C19 C20 -143.48(18) . . . . ? N18 C19 C20 C21 69.4(2) . . . . ? C26 C19 C20 C21 -168.51(16) . . . . ? N2 N1 C21 C20 0.6(3) . . . . ? N2 N1 C21 C27 179.07(16) . . . . ? C19 C20 C21 N1 -104.5(2) . . . . ? C19 C20 C21 C27 77.0(2) . . . . ? C29 N3 C28 O1 -0.1(3) . . . . ? C30 N3 C28 O1 -174.5(2) . . . . ? C29A N3 C28A O1 -18(2) . . . . ? C30A N3 C28A O1 -170.1(13) . . . . ?