#------------------------------------------------------------------------------ #$Date: 2019-05-18 05:07:56 +0300 (Sat, 18 May 2019) $ #$Revision: 215296 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/00/7700023.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_7700023 loop_ _publ_author_name 'GUILLOU, Amaury' 'Lima, Lu\'is M. P.' 'Esteban, David' 'Delgado, Rita' 'Platas-Iglesias, Carlos' 'Patinec, Veronique' 'Tripier, Raphael' _publ_section_title ; Endo- versus Exocyclic Coordination in Copper Complexes with Methylthiazolylcarboxylate Tacn Derivatives ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/C9DT01366K _journal_year 2019 _chemical_formula_moiety ; C21 H22 Cu N6 O6 S3, 4(H2 O) ; _chemical_formula_sum 'C21 H30 Cu N6 O10 S3' _chemical_formula_weight 686.23 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2016-12-05T11:40:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2019-03-07 deposited with the CCDC. 2019-05-17 downloaded from the CCDC. ; _cell_angle_alpha 85.134(4) _cell_angle_beta 86.799(3) _cell_angle_gamma 81.534(4) _cell_formula_units_Z 2 _cell_length_a 8.9546(4) _cell_length_b 10.9939(5) _cell_length_c 14.0477(6) _cell_measurement_reflns_used 6428 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.468 _cell_measurement_theta_min 3.72 _cell_volume 1361.62(11) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23) ; _computing_molecular_graphics ; ORTEP3 for Windows (Farrugia, 1997) MERCURY (Bruno et al., 2002) ; _computing_publication_material ; WinGX (Farrugia, 1999) PLATON (Spek, 1990-2003) enCIFer (Allen et al., 2004) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR-92 (Altomare et al., 1992)' _diffrn_ambient_temperature 296(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.3622 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0788548 _diffrn_orient_matrix_UB_12 0.0207305 _diffrn_orient_matrix_UB_13 0.0027687 _diffrn_orient_matrix_UB_21 -0.0133498 _diffrn_orient_matrix_UB_22 -0.0532092 _diffrn_orient_matrix_UB_23 -0.0215798 _diffrn_orient_matrix_UB_31 -0.0054252 _diffrn_orient_matrix_UB_32 -0.0319296 _diffrn_orient_matrix_UB_33 0.0458213 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0951 _diffrn_reflns_av_unetI/netI 0.0712 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 16901 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.23 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.099 _exptl_absorpt_correction_T_max 0.9471 _exptl_absorpt_correction_T_min 0.5694 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'light green' _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'prism (fragment), axis [0 0 1]' _exptl_crystal_F_000 710 _exptl_crystal_recrystallization_method 'from aqueous solution at room temperature,by slow evaporation of water' _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.403 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.08 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 397 _refine_ls_number_reflns 5560 _refine_ls_number_restraints 16 _refine_ls_restrained_S_all 1.03 _refine_ls_R_factor_all 0.063 _refine_ls_R_factor_gt 0.0468 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.1381P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1143 _refine_ls_wR_factor_ref 0.1273 _reflns_number_gt 4356 _reflns_number_total 5560 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c9dt01366k2.cif _cod_data_source_block cuno3tha-f _cod_original_cell_volume 1361.62(10) _cod_original_sg_symbol_Hall -P1 _cod_original_sg_symbol_H-M P-1 _cod_database_code 7700023 _iucr_refine_instruction_details ; TITL Cuno3tha-f at 296 K in P-1 CELL 0.71073 8.9546 10.9939 14.0477 85.134 86.799 81.534 ZERR 2.00 0.0004 0.0005 0.0006 0.004 0.003 0.004 LATT 1 SFAC C H N O S CU UNIT 42 60 12 20 6 2 MERG 2 OMIT -1 1 1 SHEL 13 0.8 DFIX 0.91 N1 H1N SADI 0.04 C1 H1N C6 H1N C7 H1N DFIX 0.85 O7 H7V O7 H7W O8 H8V O8 H8W O9 H9V O9 H9W O10 H10V O10 H10W DANG 1.34 H7V H7W H8V H8W H9V H9W H10V H10W EQIV $1 x-1, y, z+1 EQIV $2 -x+1, -y, -z+1 EQIV $3 -x+1, -y+1, -z+1 EQIV $4 x-1, y, z HTAB N1 N2 HTAB N1 N3 HTAB O7 O2_$1 HTAB O7 O2_$2 HTAB O8 O7 HTAB O8 O4_$3 HTAB O9 O8 HTAB O9 O6_$4 HTAB O10 O8 HTAB O10 O5_$2 FMAP 2 PLAN 25 SIZE 0.05 0.08 0.27 ACTA HTAB 2.00000 BOND $H L.S. 10 TEMP 23.00 WGHT 0.054700 0.138100 FVAR 1.01231 MOLE 1 C1 1 0.079429 0.084933 0.264556 11.00000 0.03509 0.03443 = 0.05386 -0.00801 -0.00264 -0.01382 AFIX 23 H1A 2 -0.025937 0.110690 0.282513 11.00000 -1.20000 H1B 2 0.098812 -0.004428 0.272319 11.00000 -1.20000 AFIX 0 C2 1 0.110438 0.128324 0.160585 11.00000 0.04271 0.03124 = 0.04749 -0.00633 -0.01101 -0.01497 AFIX 23 H2A 2 0.196101 0.075353 0.133952 11.00000 -1.20000 H2B 2 0.023205 0.123977 0.123728 11.00000 -1.20000 AFIX 0 C3 1 0.005723 0.346418 0.167864 11.00000 0.03459 0.04181 = 0.05440 -0.00366 -0.01444 -0.00116 AFIX 23 H3A 2 -0.077248 0.303151 0.191877 11.00000 -1.20000 H3B 2 -0.020830 0.388139 0.106194 11.00000 -1.20000 AFIX 0 C4 1 0.026016 0.443322 0.237380 11.00000 0.03364 0.03393 = 0.05136 -0.00363 -0.00309 0.00335 AFIX 23 H4A 2 0.087523 0.501781 0.205887 11.00000 -1.20000 H4B 2 -0.071949 0.488348 0.254455 11.00000 -1.20000 AFIX 0 C5 1 0.006036 0.311949 0.387054 11.00000 0.03757 0.03857 = 0.04586 -0.00859 0.01062 -0.00657 AFIX 23 H5A 2 -0.082967 0.300369 0.354506 11.00000 -1.20000 H5B 2 -0.027195 0.355145 0.443594 11.00000 -1.20000 AFIX 0 C6 1 0.095117 0.186227 0.416796 11.00000 0.04317 0.03889 = 0.03837 -0.00142 0.01293 -0.00593 AFIX 23 H6A 2 0.165834 0.194476 0.464897 11.00000 -1.20000 H6B 2 0.026986 0.129935 0.443346 11.00000 -1.20000 AFIX 0 C7 1 0.321582 0.055783 0.351885 11.00000 0.03831 0.02884 = 0.03464 0.00276 0.00209 -0.00824 AFIX 23 H7A 2 0.297437 -0.021445 0.383170 11.00000 -1.20000 H7B 2 0.375727 0.094206 0.396263 11.00000 -1.20000 AFIX 0 C8 1 0.421728 0.029568 0.264751 11.00000 0.03043 0.02280 = 0.03659 0.00234 -0.00325 -0.00457 C9 1 0.572795 -0.064859 0.137404 11.00000 0.04311 0.03479 = 0.04790 -0.01449 0.00650 -0.00931 AFIX 43 H9 2 0.624490 -0.114179 0.092108 11.00000 -1.20000 AFIX 0 C10 1 0.586475 0.055362 0.143788 11.00000 0.02940 0.02988 = 0.03558 -0.00518 0.00113 -0.00672 C11 1 0.694337 0.127290 0.084393 11.00000 0.03168 0.03609 = 0.03426 0.00121 -0.00340 -0.00554 C12 1 0.240295 0.288016 0.073616 11.00000 0.03814 0.03967 = 0.03448 -0.00369 -0.00949 -0.00573 AFIX 23 H12A 2 0.181470 0.305042 0.016852 11.00000 -1.20000 H12B 2 0.318338 0.218781 0.063016 11.00000 -1.20000 AFIX 0 C13 1 0.312047 0.398336 0.089678 11.00000 0.03409 0.03506 = 0.02890 0.00105 -0.00524 -0.00580 C14 1 0.383539 0.602593 0.087094 11.00000 0.04665 0.03367 = 0.04365 0.00719 -0.00785 -0.00860 AFIX 43 H14 2 0.397528 0.685045 0.078732 11.00000 -1.20000 AFIX 0 C15 1 0.458573 0.517100 0.149015 11.00000 0.03367 0.02663 = 0.03031 -0.00042 0.00167 -0.00677 C16 1 0.587920 0.531000 0.208823 11.00000 0.03311 0.03359 = 0.03337 -0.00424 0.00088 -0.00795 C17 1 0.171145 0.471031 0.373505 11.00000 0.04087 0.03366 = 0.04840 -0.01342 0.00272 -0.00289 AFIX 23 H17A 2 0.097640 0.515092 0.416317 11.00000 -1.20000 H17B 2 0.208203 0.531102 0.326956 11.00000 -1.20000 AFIX 0 C18 1 0.300207 0.404695 0.429735 11.00000 0.04553 0.03708 = 0.03393 -0.00811 -0.00062 -0.01528 C19 1 0.482039 0.329415 0.549397 11.00000 0.05551 0.06177 = 0.03035 -0.00256 -0.00497 -0.02317 AFIX 43 H19 2 0.540309 0.307456 0.602597 11.00000 -1.20000 AFIX 0 C20 1 0.520249 0.292162 0.460346 11.00000 0.04064 0.04257 = 0.02903 0.00396 -0.00611 -0.01966 C21 1 0.661920 0.212420 0.430994 11.00000 0.03878 0.03483 = 0.03999 0.00887 -0.00736 -0.01722 N1 3 0.178650 0.138037 0.328825 11.00000 0.03063 0.02673 = 0.03470 -0.00055 0.00440 -0.01008 N2 3 0.142727 0.255935 0.155149 11.00000 0.03367 0.02992 = 0.03571 -0.00380 -0.00728 -0.00504 N3 3 0.097904 0.385803 0.324127 11.00000 0.03172 0.02956 = 0.04246 -0.00589 -0.00155 -0.00675 N4 3 0.499209 0.109194 0.216853 11.00000 0.02875 0.02448 = 0.02838 0.00044 -0.00163 -0.00194 N5 3 0.415988 0.401064 0.151188 11.00000 0.02918 0.02522 = 0.02714 0.00032 -0.00127 -0.00710 N6 3 0.415108 0.334158 0.392494 11.00000 0.03571 0.03305 = 0.02953 -0.00404 -0.00090 -0.00797 O1 4 0.701110 0.232721 0.109259 11.00000 0.03862 0.03436 = 0.04466 -0.00042 0.00425 -0.00954 O2 4 0.765841 0.075459 0.016529 11.00000 0.05903 0.05331 = 0.05105 -0.01811 0.02503 -0.01655 O3 4 0.642660 0.432770 0.257055 11.00000 0.03563 0.03528 = 0.03766 -0.00117 -0.01042 -0.00658 O4 4 0.632813 0.632235 0.206711 11.00000 0.05318 0.03060 = 0.07658 -0.00530 -0.01455 -0.01549 O5 4 0.682923 0.192759 0.342816 11.00000 0.03730 0.03471 = 0.03855 0.00146 -0.00962 -0.00294 O6 4 0.752656 0.168584 0.493044 11.00000 0.04542 0.07535 = 0.04614 0.02276 -0.01845 -0.01604 S1 5 0.448798 -0.113388 0.223055 11.00000 0.04775 0.02623 = 0.05906 -0.00715 0.01005 -0.01100 S2 5 0.260586 0.537893 0.027063 11.00000 0.04749 0.04104 = 0.04203 0.01124 -0.01643 -0.00678 S3 5 0.312221 0.422007 0.549437 11.00000 0.06636 0.06286 = 0.03469 -0.01538 0.00608 -0.01871 CU 6 0.550708 0.281984 0.243391 11.00000 0.03176 0.02545 = 0.03059 0.00074 -0.00686 -0.00615 H1N 2 0.202964 0.204109 0.294462 11.00000 -1.20000 MOLE 2 O7 4 0.030730 0.142868 0.921347 11.00000 0.06483 0.07137 = 0.07616 0.01172 0.00832 -0.01837 H7V 2 -0.062111 0.136380 0.928385 11.00000 -1.50000 H7W 2 0.080469 0.074278 0.939163 11.00000 -1.50000 MOLE 3 O8 4 0.125161 0.243075 0.743320 11.00000 0.07333 0.06557 = 0.06878 0.00254 -0.01157 -0.02676 H8V 2 0.089755 0.223993 0.800285 11.00000 -1.50000 H8W 2 0.184109 0.292414 0.753794 11.00000 -1.50000 MOLE 4 O9 4 -0.166298 0.228146 0.670620 11.00000 0.09325 0.08042 = 0.08503 -0.00013 -0.01524 -0.02954 H9V 2 -0.072687 0.243697 0.675956 11.00000 -1.50000 H9W 2 -0.167872 0.225930 0.607605 11.00000 -1.50000 MOLE 5 O10 4 0.279359 0.082944 0.607841 11.00000 0.16596 0.06421 = 0.08404 0.00268 -0.02724 -0.00214 H10V 2 0.208830 0.120129 0.645784 11.00000 -1.50000 H10W 2 0.263225 0.007823 0.620862 11.00000 -1.50000 HKLF 4 REM Cuno3tha-f at 296 K in P-1 REM R1 = 0.0468 for 4356 Fo > 4sig(Fo) and 0.0630 for all 5560 data REM 397 parameters refined using 16 restraints END WGHT 0.0549 0.1263 REM Highest difference peak 0.403, deepest hole -0.508, 1-sigma level 0.080 Q1 1 0.4526 0.2491 0.2507 11.00000 0.05 0.40 Q2 1 0.3864 0.3623 0.5593 11.00000 0.05 0.37 Q3 1 0.2471 0.4446 0.4007 11.00000 0.05 0.37 Q4 1 0.5021 0.3926 0.2604 11.00000 0.05 0.35 Q5 1 0.6097 0.4355 0.2759 11.00000 0.05 0.35 Q6 1 0.2925 0.5959 0.0773 11.00000 0.05 0.35 Q7 1 0.5147 0.2146 0.1801 11.00000 0.05 0.34 Q8 1 0.0767 0.5638 0.4014 11.00000 0.05 0.34 Q9 1 0.4559 0.3451 0.2103 11.00000 0.05 0.34 Q10 1 0.5768 0.3548 0.3067 11.00000 0.05 0.33 Q11 1 0.1730 0.0626 0.5963 11.00000 0.05 0.33 Q12 1 0.4532 -0.0561 0.2636 11.00000 0.05 0.30 Q13 1 0.3838 0.3845 0.1444 11.00000 0.05 0.30 Q14 1 0.1124 0.4164 0.3429 11.00000 0.05 0.30 Q15 1 0.4706 0.4533 0.1497 11.00000 0.05 0.30 Q16 1 0.3680 -0.0545 0.2023 11.00000 0.05 0.29 Q17 1 0.6825 0.2990 0.2375 11.00000 0.05 0.29 Q18 1 0.6581 0.2196 0.2755 11.00000 0.05 0.29 Q19 1 -0.0357 0.3122 0.4011 11.00000 0.05 0.29 Q20 1 0.5234 0.5202 0.1823 11.00000 0.05 0.29 Q21 1 0.4749 0.3195 0.0950 11.00000 0.05 0.28 Q22 1 0.3372 -0.1417 0.2372 11.00000 0.05 0.28 Q23 1 0.3448 0.4048 0.1786 11.00000 0.05 0.27 Q24 1 0.0389 0.3889 0.1939 11.00000 0.05 0.27 Q25 1 0.7278 0.1951 0.1351 11.00000 0.05 0.27 ; loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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 C1 C 0.0794(4) 0.0849(3) 0.2646(2) 0.0399(8) Uani 1 1 d D H1A H -0.0259 0.1107 0.2825 0.048 Uiso 1 1 calc R H1B H 0.0988 -0.0044 0.2723 0.048 Uiso 1 1 calc R C2 C 0.1104(4) 0.1283(3) 0.1606(2) 0.0390(8) Uani 1 1 d . H2A H 0.1961 0.0754 0.134 0.047 Uiso 1 1 calc R H2B H 0.0232 0.124 0.1237 0.047 Uiso 1 1 calc R C3 C 0.0057(4) 0.3464(3) 0.1679(3) 0.0436(8) Uani 1 1 d . H3A H -0.0772 0.3032 0.1919 0.052 Uiso 1 1 calc R H3B H -0.0208 0.3881 0.1062 0.052 Uiso 1 1 calc R C4 C 0.0260(4) 0.4433(3) 0.2374(3) 0.0404(8) Uani 1 1 d . H4A H 0.0875 0.5018 0.2059 0.048 Uiso 1 1 calc R H4B H -0.0719 0.4883 0.2545 0.048 Uiso 1 1 calc R C5 C 0.0060(4) 0.3119(3) 0.3871(3) 0.0407(8) Uani 1 1 d . H5A H -0.083 0.3004 0.3545 0.049 Uiso 1 1 calc R H5B H -0.0272 0.3551 0.4436 0.049 Uiso 1 1 calc R C6 C 0.0951(4) 0.1862(3) 0.4168(2) 0.0408(8) Uani 1 1 d D H6A H 0.1658 0.1945 0.4649 0.049 Uiso 1 1 calc R H6B H 0.027 0.1299 0.4433 0.049 Uiso 1 1 calc R C7 C 0.3216(3) 0.0558(3) 0.3519(2) 0.0340(7) Uani 1 1 d D H7A H 0.2974 -0.0214 0.3832 0.041 Uiso 1 1 calc R H7B H 0.3757 0.0942 0.3963 0.041 Uiso 1 1 calc R C8 C 0.4217(3) 0.0296(3) 0.2648(2) 0.0301(7) Uani 1 1 d . C9 C 0.5728(4) -0.0649(3) 0.1374(3) 0.0412(8) Uani 1 1 d . H9 H 0.6245 -0.1142 0.0921 0.049 Uiso 1 1 calc R C10 C 0.5865(3) 0.0554(3) 0.1438(2) 0.0313(7) Uani 1 1 d . C11 C 0.6943(3) 0.1273(3) 0.0844(2) 0.0341(7) Uani 1 1 d . C12 C 0.2403(4) 0.2880(3) 0.0736(2) 0.0371(7) Uani 1 1 d . H12A H 0.1815 0.305 0.0169 0.044 Uiso 1 1 calc R H12B H 0.3183 0.2188 0.063 0.044 Uiso 1 1 calc R C13 C 0.3120(3) 0.3983(3) 0.0897(2) 0.0327(7) Uani 1 1 d . C14 C 0.3835(4) 0.6026(3) 0.0871(2) 0.0414(8) Uani 1 1 d . H14 H 0.3975 0.685 0.0787 0.05 Uiso 1 1 calc R C15 C 0.4586(3) 0.5171(3) 0.1490(2) 0.0302(7) Uani 1 1 d . C16 C 0.5879(3) 0.5310(3) 0.2088(2) 0.0330(7) Uani 1 1 d . C17 C 0.1711(4) 0.4710(3) 0.3735(3) 0.0408(8) Uani 1 1 d . H17A H 0.0976 0.5151 0.4163 0.049 Uiso 1 1 calc R H17B H 0.2082 0.5311 0.327 0.049 Uiso 1 1 calc R C18 C 0.3002(4) 0.4047(3) 0.4297(2) 0.0376(7) Uani 1 1 d . C19 C 0.4820(4) 0.3294(4) 0.5494(2) 0.0477(9) Uani 1 1 d . H19 H 0.5403 0.3075 0.6026 0.057 Uiso 1 1 calc R C20 C 0.5202(4) 0.2922(3) 0.4603(2) 0.0362(7) Uani 1 1 d . C21 C 0.6619(4) 0.2124(3) 0.4310(2) 0.0371(7) Uani 1 1 d . N1 N 0.1786(3) 0.1380(2) 0.32882(18) 0.0304(6) Uani 1 1 d D N2 N 0.1427(3) 0.2559(2) 0.15515(18) 0.0328(6) Uani 1 1 d . N3 N 0.0979(3) 0.3858(2) 0.32413(19) 0.0342(6) Uani 1 1 d . N4 N 0.4992(3) 0.1092(2) 0.21685(16) 0.0275(5) Uani 1 1 d . N5 N 0.4160(3) 0.4011(2) 0.15119(16) 0.0270(5) Uani 1 1 d . N6 N 0.4151(3) 0.3342(2) 0.39249(17) 0.0324(6) Uani 1 1 d . O1 O 0.7011(2) 0.2327(2) 0.10926(16) 0.0392(5) Uani 1 1 d . O2 O 0.7658(3) 0.0755(2) 0.01653(18) 0.0538(7) Uani 1 1 d . O3 O 0.6427(2) 0.4328(2) 0.25705(15) 0.0358(5) Uani 1 1 d . O4 O 0.6328(3) 0.6322(2) 0.2067(2) 0.0520(7) Uani 1 1 d . O5 O 0.6829(2) 0.1928(2) 0.34282(16) 0.0370(5) Uani 1 1 d . O6 O 0.7527(3) 0.1686(3) 0.49304(17) 0.0559(7) Uani 1 1 d . S1 S 0.44880(10) -0.11339(8) 0.22306(7) 0.0440(2) Uani 1 1 d . S2 S 0.26059(10) 0.53789(8) 0.02706(6) 0.0438(2) Uani 1 1 d . S3 S 0.31222(12) 0.42201(10) 0.54944(6) 0.0533(3) Uani 1 1 d . Cu Cu 0.55071(4) 0.28198(3) 0.24339(2) 0.02902(13) Uani 1 1 d . H1N H 0.203(3) 0.2041(18) 0.2945(15) 0.035 Uiso 1 1 d D O7 O 0.0307(4) 0.1429(3) 0.9213(3) 0.0714(9) Uani 1 1 d D H7V H -0.062(2) 0.136(5) 0.928(4) 0.107 Uiso 1 1 d D H7W H 0.080(5) 0.074(3) 0.939(4) 0.107 Uiso 1 1 d D O8 O 0.1252(4) 0.2431(3) 0.7433(2) 0.0677(8) Uani 1 1 d D H8V H 0.090(5) 0.224(5) 0.8003(19) 0.101 Uiso 1 1 d D H8W H 0.184(5) 0.292(4) 0.754(4) 0.101 Uiso 1 1 d D O9 O -0.1663(4) 0.2281(4) 0.6706(3) 0.0844(10) Uani 1 1 d D H9V H -0.073(3) 0.244(6) 0.676(4) 0.127 Uiso 1 1 d D H9W H -0.168(6) 0.226(6) 0.6076(16) 0.127 Uiso 1 1 d D O10 O 0.2794(6) 0.0829(4) 0.6078(3) 0.1058(14) Uani 1 1 d D H10V H 0.209(6) 0.120(5) 0.646(4) 0.159 Uiso 1 1 d D H10W H 0.263(8) 0.008(2) 0.621(5) 0.159 Uiso 1 1 d 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 C1 0.0351(17) 0.0344(18) 0.054(2) -0.0080(15) -0.0026(16) -0.0138(14) C2 0.0427(18) 0.0312(17) 0.0475(19) -0.0063(14) -0.0110(16) -0.0150(15) C3 0.0346(17) 0.042(2) 0.054(2) -0.0037(16) -0.0144(16) -0.0012(15) C4 0.0336(17) 0.0339(18) 0.051(2) -0.0036(15) -0.0031(15) 0.0034(14) C5 0.0376(17) 0.0386(19) 0.0459(19) -0.0086(15) 0.0106(16) -0.0066(15) C6 0.0432(18) 0.0389(19) 0.0384(18) -0.0014(15) 0.0129(16) -0.0059(15) C7 0.0383(17) 0.0288(16) 0.0346(16) 0.0028(13) 0.0021(14) -0.0082(14) C8 0.0304(15) 0.0228(15) 0.0366(16) 0.0023(12) -0.0032(13) -0.0046(12) C9 0.0431(18) 0.0348(18) 0.048(2) -0.0145(15) 0.0065(16) -0.0093(15) C10 0.0294(15) 0.0299(16) 0.0356(16) -0.0052(13) 0.0011(13) -0.0067(13) C11 0.0317(16) 0.0361(18) 0.0343(17) 0.0012(14) -0.0034(14) -0.0055(14) C12 0.0381(17) 0.0397(18) 0.0345(17) -0.0037(14) -0.0095(14) -0.0057(15) C13 0.0341(16) 0.0351(17) 0.0289(15) 0.0011(13) -0.0052(13) -0.0058(14) C14 0.0466(19) 0.0337(18) 0.0437(19) 0.0072(15) -0.0078(16) -0.0086(15) C15 0.0337(15) 0.0266(15) 0.0303(15) -0.0004(12) 0.0017(13) -0.0068(13) C16 0.0331(16) 0.0336(17) 0.0334(16) -0.0042(13) 0.0009(14) -0.0079(14) C17 0.0409(18) 0.0337(18) 0.048(2) -0.0134(15) 0.0027(16) -0.0029(15) C18 0.0455(19) 0.0371(18) 0.0339(17) -0.0081(14) -0.0006(15) -0.0153(16) C19 0.056(2) 0.062(2) 0.0304(17) -0.0026(16) -0.0050(16) -0.0232(19) C20 0.0406(17) 0.0426(19) 0.0290(16) 0.0040(14) -0.0061(14) -0.0197(15) C21 0.0388(17) 0.0348(17) 0.0400(18) 0.0089(14) -0.0074(15) -0.0172(14) N1 0.0306(13) 0.0267(13) 0.0347(14) -0.0006(11) 0.0044(11) -0.0101(11) N2 0.0337(13) 0.0299(14) 0.0357(14) -0.0038(11) -0.0073(12) -0.0050(11) N3 0.0317(13) 0.0296(14) 0.0425(15) -0.0059(12) -0.0016(12) -0.0068(11) N4 0.0287(12) 0.0245(12) 0.0284(13) 0.0004(10) -0.0016(11) -0.0019(10) N5 0.0292(12) 0.0252(13) 0.0271(12) 0.0003(10) -0.0013(11) -0.0071(10) N6 0.0357(14) 0.0331(14) 0.0295(13) -0.0040(11) -0.0009(12) -0.0080(12) O1 0.0386(12) 0.0344(13) 0.0447(13) -0.0004(10) 0.0043(11) -0.0095(10) O2 0.0590(15) 0.0533(16) 0.0510(15) -0.0181(13) 0.0250(13) -0.0165(13) O3 0.0356(11) 0.0353(12) 0.0377(12) -0.0012(10) -0.0104(10) -0.0066(10) O4 0.0532(15) 0.0306(13) 0.0766(18) -0.0053(12) -0.0145(14) -0.0155(12) O5 0.0373(12) 0.0347(12) 0.0386(13) 0.0015(10) -0.0096(10) -0.0029(10) O6 0.0454(14) 0.0753(19) 0.0461(14) 0.0228(13) -0.0185(12) -0.0160(13) S1 0.0478(5) 0.0262(4) 0.0591(5) -0.0071(4) 0.0101(4) -0.0110(4) S2 0.0475(5) 0.0410(5) 0.0420(5) 0.0112(4) -0.0164(4) -0.0068(4) S3 0.0664(6) 0.0629(6) 0.0347(5) -0.0154(4) 0.0061(5) -0.0187(5) Cu 0.0318(2) 0.0254(2) 0.0306(2) 0.00074(15) -0.00686(16) -0.00615(16) O7 0.0648(19) 0.071(2) 0.076(2) 0.0117(17) 0.0083(18) -0.0184(17) O8 0.073(2) 0.066(2) 0.0688(19) 0.0025(16) -0.0116(17) -0.0268(16) O9 0.093(2) 0.080(2) 0.085(2) 0.000(2) -0.015(2) -0.030(2) O10 0.166(4) 0.064(2) 0.084(3) 0.003(2) -0.027(3) -0.002(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 0 0.05 0 1 0 0.02 1 0 0 0.025 -1 0 0 0.025 0 0 -1 0.17 0 1 1 0.02 1 1 1 0.025 -1 -1 -1 0.11 3 5 2 0.01 1 3 1 0.005 -3 -2 5 0.085 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 C2 110.4(2) N1 C1 H1A 109.6 C2 C1 H1A 109.6 N1 C1 H1B 109.6 C2 C1 H1B 109.6 H1A C1 H1B 108.1 N2 C2 C1 109.3(3) N2 C2 H2A 109.8 C1 C2 H2A 109.8 N2 C2 H2B 109.8 C1 C2 H2B 109.8 H2A C2 H2B 108.3 N2 C3 C4 112.8(3) N2 C3 H3A 109 C4 C3 H3A 109 N2 C3 H3B 109 C4 C3 H3B 109 H3A C3 H3B 107.8 N3 C4 C3 111.4(3) N3 C4 H4A 109.3 C3 C4 H4A 109.3 N3 C4 H4B 109.3 C3 C4 H4B 109.3 H4A C4 H4B 108 N3 C5 C6 111.0(3) N3 C5 H5A 109.4 C6 C5 H5A 109.4 N3 C5 H5B 109.4 C6 C5 H5B 109.4 H5A C5 H5B 108 N1 C6 C5 107.4(3) N1 C6 H6A 110.2 C5 C6 H6A 110.2 N1 C6 H6B 110.2 C5 C6 H6B 110.2 H6A C6 H6B 108.5 N1 C7 C8 112.5(2) N1 C7 H7A 109.1 C8 C7 H7A 109.1 N1 C7 H7B 109.1 C8 C7 H7B 109.1 H7A C7 H7B 107.8 N4 C8 C7 124.8(3) N4 C8 S1 114.5(2) C7 C8 S1 120.6(2) C10 C9 S1 111.0(3) C10 C9 H9 124.5 S1 C9 H9 124.5 C9 C10 N4 114.0(3) C9 C10 C11 126.0(3) N4 C10 C11 119.8(3) O2 C11 O1 127.6(3) O2 C11 C10 116.9(3) O1 C11 C10 115.5(3) N2 C12 C13 111.1(3) N2 C12 H12A 109.4 C13 C12 H12A 109.4 N2 C12 H12B 109.4 C13 C12 H12B 109.4 H12A C12 H12B 108 N5 C13 C12 125.3(3) N5 C13 S2 113.4(2) C12 C13 S2 121.3(2) C15 C14 S2 110.3(3) C15 C14 H14 124.9 S2 C14 H14 124.9 C14 C15 N5 114.7(3) C14 C15 C16 128.0(3) N5 C15 C16 117.1(2) O4 C16 O3 126.1(3) O4 C16 C15 119.2(3) O3 C16 C15 114.6(3) N3 C17 C18 111.6(3) N3 C17 H17A 109.3 C18 C17 H17A 109.3 N3 C17 H17B 109.3 C18 C17 H17B 109.3 H17A C17 H17B 108 N6 C18 C17 123.8(3) N6 C18 S3 114.3(2) C17 C18 S3 121.8(2) C20 C19 S3 110.2(3) C20 C19 H19 124.9 S3 C19 H19 124.9 C19 C20 N6 115.0(3) C19 C20 C21 126.3(3) N6 C20 C21 118.7(3) O6 C21 O5 123.5(3) O6 C21 C20 118.8(3) O5 C21 C20 117.6(3) C7 N1 C6 112.1(2) C7 N1 C1 114.2(2) C6 N1 C1 113.1(2) C7 N1 H1N 107.7(15) C6 N1 H1N 105.2(15) C1 N1 H1N 103.6(15) C12 N2 C2 114.1(3) C12 N2 C3 113.8(3) C2 N2 C3 112.8(3) C5 N3 C17 113.8(3) C5 N3 C4 115.2(3) C17 N3 C4 112.9(3) C8 N4 C10 110.9(2) C8 N4 Cu 133.9(2) C10 N4 Cu 113.88(19) C13 N5 C15 111.2(2) C13 N5 Cu 139.6(2) C15 N5 Cu 108.96(18) C18 N6 C20 110.6(3) C18 N6 Cu 144.1(2) C20 N6 Cu 103.10(18) C11 O1 Cu 113.7(2) C16 O3 Cu 117.16(19) C21 O5 Cu 122.3(2) C9 S1 C8 89.58(15) C14 S2 C13 90.46(15) C19 S3 C18 89.86(17) O5 Cu O3 89.36(9) O5 Cu N5 170.40(9) O3 Cu N5 82.16(9) O5 Cu N4 86.15(9) O3 Cu N4 167.83(9) N5 Cu N4 103.04(9) O5 Cu O1 99.08(9) O3 Cu O1 92.92(8) N5 Cu O1 85.88(9) N4 Cu O1 76.67(9) O5 Cu N6 76.33(9) O3 Cu N6 83.89(9) N5 Cu N6 98.21(9) N4 Cu N6 105.95(9) O1 Cu N6 174.39(8) H7V O7 H7W 108(4) H8V O8 H8W 102(4) H9V O9 H9W 100(4) H10V O10 H10W 99(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.509(4) C1 C2 1.521(5) C1 H1A 0.97 C1 H1B 0.97 C2 N2 1.468(4) C2 H2A 0.97 C2 H2B 0.97 C3 N2 1.474(4) C3 C4 1.541(5) C3 H3A 0.97 C3 H3B 0.97 C4 N3 1.462(4) C4 H4A 0.97 C4 H4B 0.97 C5 N3 1.453(4) C5 C6 1.528(5) C5 H5A 0.97 C5 H5B 0.97 C6 N1 1.503(4) C6 H6A 0.97 C6 H6B 0.97 C7 N1 1.489(4) C7 C8 1.499(4) C7 H7A 0.97 C7 H7B 0.97 C8 N4 1.314(4) C8 S1 1.703(3) C9 C10 1.356(4) C9 S1 1.698(4) C9 H9 0.93 C10 N4 1.375(4) C10 C11 1.509(4) C11 O2 1.249(4) C11 O1 1.249(4) C12 N2 1.453(4) C12 C13 1.492(4) C12 H12A 0.97 C12 H12B 0.97 C13 N5 1.310(3) C13 S2 1.717(3) C14 C15 1.354(4) C14 S2 1.693(3) C14 H14 0.93 C15 N5 1.382(4) C15 C16 1.501(4) C16 O4 1.235(4) C16 O3 1.274(4) C17 N3 1.460(4) C17 C18 1.499(5) C17 H17A 0.97 C17 H17B 0.97 C18 N6 1.307(4) C18 S3 1.719(3) C19 C20 1.359(5) C19 S3 1.701(4) C19 H19 0.93 C20 N6 1.380(4) C20 C21 1.491(5) C21 O6 1.243(4) C21 O5 1.274(4) N1 H1N 0.885(18) N4 Cu 2.087(2) N5 Cu 2.066(2) N6 Cu 2.430(2) O1 Cu 2.309(2) O3 Cu 1.984(2) O5 Cu 1.981(2) O7 H7V 0.844(19) O7 H7W 0.843(19) O8 H8V 0.865(19) O8 H8W 0.837(19) O9 H9V 0.888(19) O9 H9W 0.889(19) O10 H10V 0.88(2) O10 H10W 0.86(2) 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 N1 H1N N2 0.885(18) 2.07(2) 2.677(4) 124.9(19) . N1 H1N N3 0.885(18) 2.14(2) 2.710(4) 121.2(19) . O7 H7V O2 0.844(19) 2.07(4) 2.821(4) 147(5) 1_456 O7 H7W O2 0.843(19) 2.06(2) 2.894(4) 170(5) 2_656 O8 H8V O7 0.865(19) 1.94(2) 2.785(5) 167(5) . O8 H8W O4 0.837(19) 2.06(2) 2.877(4) 164(5) 2_666 O9 H9V O8 0.888(19) 2.05(3) 2.887(5) 156(5) . O9 H9W O6 0.889(19) 1.98(3) 2.792(4) 151(5) 1_455 O10 H10V O8 0.88(2) 2.04(3) 2.861(5) 155(7) . O10 H10W O5 0.86(2) 2.21(3) 3.025(4) 158(6) 2_656