#------------------------------------------------------------------------------ #$Date: 2020-10-06 12:01:12 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257559 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/51/7705176.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_7705176 loop_ _publ_author_name 'Li, Yinghua' 'Fan, Weibin' 'Zhang, Zilong' 'Xie, Xingkun' 'Xiang, Shiqun' 'Huang, Deguang' _publ_section_title ; Copper(II)-hydroxide facilitated C-C bond formation: the carboxamido pyridine system versus the methylimino pyridine system. ; _journal_issue 35 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 12189 _journal_page_last 12196 _journal_paper_doi 10.1039/d0dt02288h _journal_volume 49 _journal_year 2020 _chemical_formula_moiety 'C27 H31 Cu N4 O2, C F3 S O3' _chemical_formula_sum 'C28 H31 Cu F3 N4 O5 S' _chemical_formula_weight 656.17 _chemical_name_common '[Cu(N3-ligand)(DMF)](OTf)' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-07-20 deposited with the CCDC. 2020-08-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.1134(15) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.2458(2) _cell_length_b 8.57344(11) _cell_length_c 24.9685(4) _cell_measurement_reflns_used 6829 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 73.5660 _cell_measurement_theta_min 5.3870 _cell_volume 2957.49(8) _computing_cell_refinement 'CrysAlisPro, Agilent Technologies' _computing_data_collection 'CrysAlisPro, Agilent Technologies' _computing_data_reduction 'CrysAlisPro, Agilent Technologies' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.5594 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_unetI/netI 0.0214 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 11672 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.999 _diffrn_reflns_theta_min 3.199 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.256 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.76840 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies,Version 1.171.36.28 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_description column _exptl_crystal_F_000 1356 _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.666 _refine_diff_density_min -0.698 _refine_diff_density_rms 0.081 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 379 _refine_ls_number_reflns 5675 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0424 _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^)+(0.0581P)^2^+6.9168P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1163 _refine_ls_wR_factor_ref 0.1219 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4975 _reflns_number_total 5675 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02288h2.cif _cod_data_source_block Complex10 _cod_depositor_comments 'Adding full bibliography for 7705173--7705180.cif.' _cod_original_cell_volume 2957.48(7) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7705176 _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 0.571 _shelx_estimated_absorpt_t_max 0.806 _shelx_res_file ; TITL CF solution in P21/c full.res created by SHELXL-2018/3 at 21:21:34 on 20-Jul-2020 CELL 1.54184 14.24577 8.57344 24.96851 90 104.1134 90 ZERR 4 0.00021 0.00011 0.00036 0 0.0015 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cu N O S F UNIT 112 124 4 16 20 4 12 TEMP -173 SIZE 0.28 0.12 0.10 REM green column OMIT -2 142 ACTA L.S. 8 PLAN 3 BOND $H CONF fmap 2 WGHT 0.058100 6.916800 FVAR 4.32738 CU1 3 0.653773 0.566780 0.286457 11.00000 0.01147 0.01636 = 0.01214 0.00002 0.00178 0.00195 O1 5 0.408924 0.821611 0.226752 11.00000 0.01513 0.01590 = 0.02328 -0.00025 0.00075 0.00308 O2 5 0.721862 0.550742 0.362890 11.00000 0.01744 0.02366 = 0.01404 -0.00065 0.00074 0.00434 N1 4 0.536817 0.694927 0.286841 11.00000 0.01322 0.01716 = 0.01586 -0.00089 0.00196 0.00274 N2 4 0.614220 0.619403 0.209570 11.00000 0.01428 0.01534 = 0.01457 -0.00107 0.00329 -0.00143 N3 4 0.777351 0.509724 0.260420 11.00000 0.01138 0.01755 = 0.01961 -0.00229 0.00261 -0.00154 N4 4 0.747861 0.599812 0.454287 11.00000 0.01967 0.01758 = 0.01392 -0.00010 0.00007 -0.00076 C1 1 0.485068 0.742268 0.237678 11.00000 0.01368 0.01206 = 0.01795 -0.00055 0.00124 -0.00169 C2 1 0.530837 0.693953 0.191750 11.00000 0.01485 0.01304 = 0.01707 -0.00033 0.00138 -0.00239 C3 1 0.497419 0.729336 0.136123 11.00000 0.02112 0.01779 = 0.01824 -0.00015 -0.00155 -0.00117 AFIX 43 H3A 2 0.436983 0.780111 0.122678 11.00000 -1.20000 AFIX 0 C4 1 0.554608 0.688577 0.100780 11.00000 0.02884 0.02716 = 0.01438 0.00007 0.00161 -0.00314 AFIX 43 H4A 2 0.533014 0.711443 0.062516 11.00000 -1.20000 AFIX 0 C5 1 0.643431 0.614465 0.120491 11.00000 0.02510 0.02592 = 0.01696 -0.00304 0.00668 -0.00437 AFIX 43 H5A 2 0.683392 0.588297 0.096420 11.00000 -1.20000 AFIX 0 C6 1 0.671532 0.580190 0.176442 11.00000 0.01652 0.01728 = 0.01730 -0.00371 0.00466 -0.00299 C7 1 0.766503 0.517289 0.207974 11.00000 0.01380 0.01932 = 0.02104 -0.00467 0.00480 -0.00215 C8 1 0.841715 0.481136 0.177210 11.00000 0.02153 0.04510 = 0.02584 -0.00683 0.00951 0.00404 AFIX 33 H8A 2 0.814389 0.496371 0.137568 11.00000 -1.50000 H8B 2 0.897293 0.550747 0.189785 11.00000 -1.50000 H8C 2 0.862760 0.372591 0.184112 11.00000 -1.50000 AFIX 0 C9 1 0.871002 0.484982 0.297139 11.00000 0.01040 0.02741 = 0.01782 -0.00585 0.00247 -0.00016 C10 1 0.930485 0.616049 0.311136 11.00000 0.01760 0.03336 = 0.03098 -0.00802 0.00615 -0.00560 C11 1 1.018888 0.596992 0.349266 11.00000 0.01893 0.04787 = 0.03732 -0.00985 -0.00015 -0.01260 AFIX 43 H11A 2 1.060637 0.684076 0.359529 11.00000 -1.20000 AFIX 0 C12 1 1.046524 0.452921 0.372317 11.00000 0.01487 0.06589 = 0.02711 -0.00147 -0.00279 -0.00444 AFIX 43 H12A 2 1.107618 0.441285 0.397813 11.00000 -1.20000 AFIX 0 C13 1 0.986253 0.325502 0.358688 11.00000 0.01913 0.04529 = 0.02588 0.00459 0.00217 0.00735 AFIX 43 H13A 2 1.006135 0.227226 0.375162 11.00000 -1.20000 AFIX 0 C14 1 0.896361 0.339136 0.320975 11.00000 0.01683 0.03110 = 0.02085 -0.00402 0.00405 0.00264 C15 1 0.830055 0.202039 0.306666 11.00000 0.02407 0.02604 = 0.04025 0.00146 -0.00095 0.00320 AFIX 33 H15A 2 0.860195 0.110494 0.327421 11.00000 -1.50000 H15B 2 0.768714 0.224910 0.316211 11.00000 -1.50000 H15C 2 0.817808 0.180881 0.266991 11.00000 -1.50000 AFIX 0 C16 1 0.898870 0.774469 0.287198 11.00000 0.02961 0.02712 = 0.06437 -0.00597 0.00517 -0.01078 AFIX 33 H16A 2 0.835228 0.765918 0.261261 11.00000 -1.50000 H16B 2 0.894847 0.846485 0.317037 11.00000 -1.50000 H16C 2 0.945987 0.813970 0.267737 11.00000 -1.50000 AFIX 0 C17 1 0.507198 0.731617 0.335946 11.00000 0.01537 0.01760 = 0.01589 0.00231 0.00308 0.00604 C18 1 0.564961 0.834171 0.373877 11.00000 0.01676 0.01896 = 0.01911 0.00044 0.00256 0.00648 C19 1 0.543178 0.855918 0.425011 11.00000 0.02395 0.02607 = 0.01790 -0.00334 0.00168 0.00697 AFIX 43 H19A 2 0.582141 0.923541 0.451495 11.00000 -1.20000 AFIX 0 C20 1 0.465109 0.779615 0.437486 11.00000 0.02775 0.03391 = 0.01800 0.00387 0.00773 0.01199 AFIX 43 H20A 2 0.451053 0.795249 0.472386 11.00000 -1.20000 AFIX 0 C21 1 0.407784 0.680947 0.399240 11.00000 0.02012 0.02966 = 0.02310 0.00795 0.00870 0.00593 AFIX 43 H21A 2 0.354174 0.630242 0.408047 11.00000 -1.20000 AFIX 0 C22 1 0.427586 0.654739 0.347801 11.00000 0.01514 0.01926 = 0.02225 0.00397 0.00352 0.00523 C23 1 0.363797 0.549497 0.306255 11.00000 0.01815 0.02341 = 0.02834 0.00237 0.00257 -0.00101 AFIX 33 H23A 2 0.388190 0.544614 0.272831 11.00000 -1.50000 H23B 2 0.363980 0.444638 0.321905 11.00000 -1.50000 H23C 2 0.297603 0.590577 0.296923 11.00000 -1.50000 AFIX 0 C24 1 0.648769 0.919708 0.360109 11.00000 0.01964 0.02038 = 0.02429 -0.00428 0.00346 -0.00005 AFIX 33 H24A 2 0.653450 0.890765 0.322878 11.00000 -1.50000 H24B 2 0.638293 1.032421 0.361657 11.00000 -1.50000 H24C 2 0.708940 0.891433 0.386859 11.00000 -1.50000 AFIX 0 C25 1 0.693475 0.552747 0.406678 11.00000 0.01755 0.01433 = 0.01879 0.00048 0.00039 0.00199 AFIX 43 H25A 2 0.629513 0.518555 0.405344 11.00000 -1.20000 AFIX 0 C26 1 0.846143 0.658143 0.459831 11.00000 0.02154 0.02869 = 0.02486 0.00023 -0.00135 -0.00519 AFIX 33 H26A 2 0.874315 0.687129 0.498369 11.00000 -1.50000 H26B 2 0.885724 0.576611 0.448691 11.00000 -1.50000 H26C 2 0.844307 0.749811 0.436150 11.00000 -1.50000 AFIX 0 C27 1 0.710829 0.597848 0.503955 11.00000 0.03151 0.02346 = 0.01622 0.00098 0.00553 0.00201 AFIX 33 H27A 2 0.760812 0.636583 0.535378 11.00000 -1.50000 H27B 2 0.653482 0.664763 0.498367 11.00000 -1.50000 H27C 2 0.693361 0.490883 0.511428 11.00000 -1.50000 AFIX 0 C28 1 0.125160 0.840233 0.510580 11.00000 0.02304 0.02496 = 0.03408 -0.00356 0.01097 -0.00053 F1 7 0.103944 0.695146 0.523384 11.00000 0.04903 0.03078 = 0.08520 -0.00121 0.04390 -0.01121 F2 7 0.049518 0.891391 0.472143 11.00000 0.02157 0.06348 = 0.05097 -0.01434 0.00065 0.01471 F3 7 0.132958 0.928542 0.555400 11.00000 0.03663 0.03921 = 0.03256 -0.00684 0.01794 0.00301 S1 6 0.234937 0.844052 0.485567 11.00000 0.01634 0.01753 = 0.01643 -0.00119 0.00389 -0.00140 O3 5 0.246768 1.007858 0.475460 11.00000 0.03859 0.01898 = 0.02949 0.00212 0.01305 -0.00445 O4 5 0.209344 0.748443 0.436559 11.00000 0.02205 0.02617 = 0.01983 -0.00652 0.00197 0.00144 O5 5 0.307506 0.778669 0.530435 11.00000 0.02133 0.03035 = 0.02076 -0.00111 -0.00106 0.00223 HKLF 4 REM CF solution in P21/c REM wR2 = 0.1219, GooF = S = 1.028, Restrained GooF = 1.028 for all data REM R1 = 0.0424 for 4975 Fo > 4sig(Fo) and 0.0489 for all 5675 data REM 379 parameters refined using 0 restraints END WGHT 0.0581 6.9165 REM Highest difference peak 0.666, deepest hole -0.698, 1-sigma level 0.081 Q1 1 0.8899 0.5936 0.4879 11.00000 0.05 0.67 Q2 1 0.6427 0.5635 0.4943 11.00000 0.05 0.65 Q3 1 0.6222 0.9710 0.3217 11.00000 0.05 0.65 ; _shelx_res_checksum 24972 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 Cu1 Cu 0.65377(3) 0.56678(4) 0.28646(2) 0.01351(12) Uani 1 1 d . . . . . O1 O 0.40892(13) 0.8216(2) 0.22675(8) 0.0188(4) Uani 1 1 d . . . . . O2 O 0.72186(13) 0.5507(2) 0.36289(7) 0.0189(4) Uani 1 1 d . . . . . N1 N 0.53682(15) 0.6949(3) 0.28684(9) 0.0157(4) Uani 1 1 d . . . . . N2 N 0.61422(15) 0.6194(3) 0.20957(9) 0.0148(4) Uani 1 1 d . . . . . N3 N 0.77735(15) 0.5097(3) 0.26042(9) 0.0164(4) Uani 1 1 d . . . . . N4 N 0.74786(16) 0.5998(3) 0.45429(9) 0.0178(5) Uani 1 1 d . . . . . C1 C 0.48507(18) 0.7423(3) 0.23768(10) 0.0150(5) Uani 1 1 d . . . . . C2 C 0.53084(18) 0.6940(3) 0.19175(11) 0.0154(5) Uani 1 1 d . . . . . C3 C 0.4974(2) 0.7293(3) 0.13612(11) 0.0201(6) Uani 1 1 d . . . . . H3A H 0.436983 0.780111 0.122678 0.024 Uiso 1 1 calc R U . . . C4 C 0.5546(2) 0.6886(3) 0.10078(11) 0.0241(6) Uani 1 1 d . . . . . H4A H 0.533014 0.711443 0.062516 0.029 Uiso 1 1 calc R U . . . C5 C 0.6434(2) 0.6145(3) 0.12049(11) 0.0224(6) Uani 1 1 d . . . . . H5A H 0.683392 0.588297 0.096420 0.027 Uiso 1 1 calc R U . . . C6 C 0.67153(19) 0.5802(3) 0.17644(11) 0.0169(5) Uani 1 1 d . . . . . C7 C 0.76650(19) 0.5173(3) 0.20797(11) 0.0180(5) Uani 1 1 d . . . . . C8 C 0.8417(2) 0.4811(4) 0.17721(13) 0.0302(7) Uani 1 1 d . . . . . H8A H 0.814389 0.496371 0.137568 0.045 Uiso 1 1 calc R U . . . H8B H 0.897293 0.550747 0.189785 0.045 Uiso 1 1 calc R U . . . H8C H 0.862760 0.372591 0.184112 0.045 Uiso 1 1 calc R U . . . C9 C 0.87100(19) 0.4850(3) 0.29714(11) 0.0187(5) Uani 1 1 d . . . . . C10 C 0.9305(2) 0.6160(4) 0.31114(13) 0.0273(6) Uani 1 1 d . . . . . C11 C 1.0189(2) 0.5970(4) 0.34927(14) 0.0359(8) Uani 1 1 d . . . . . H11A H 1.060637 0.684076 0.359529 0.043 Uiso 1 1 calc R U . . . C12 C 1.0465(2) 0.4529(5) 0.37232(14) 0.0373(8) Uani 1 1 d . . . . . H12A H 1.107618 0.441285 0.397813 0.045 Uiso 1 1 calc R U . . . C13 C 0.9863(2) 0.3255(4) 0.35869(13) 0.0307(7) Uani 1 1 d . . . . . H13A H 1.006135 0.227226 0.375162 0.037 Uiso 1 1 calc R U . . . C14 C 0.8964(2) 0.3391(4) 0.32097(12) 0.0230(6) Uani 1 1 d . . . . . C15 C 0.8301(2) 0.2020(4) 0.30667(14) 0.0316(7) Uani 1 1 d . . . . . H15A H 0.860195 0.110494 0.327421 0.047 Uiso 1 1 calc R U . . . H15B H 0.768714 0.224910 0.316211 0.047 Uiso 1 1 calc R U . . . H15C H 0.817808 0.180881 0.266991 0.047 Uiso 1 1 calc R U . . . C16 C 0.8989(3) 0.7745(4) 0.28720(17) 0.0415(9) Uani 1 1 d . . . . . H16A H 0.835228 0.765918 0.261261 0.062 Uiso 1 1 calc R U . . . H16B H 0.894847 0.846485 0.317037 0.062 Uiso 1 1 calc R U . . . H16C H 0.945987 0.813970 0.267737 0.062 Uiso 1 1 calc R U . . . C17 C 0.50720(18) 0.7316(3) 0.33595(11) 0.0164(5) Uani 1 1 d . . . . . C18 C 0.56496(19) 0.8342(3) 0.37388(11) 0.0186(5) Uani 1 1 d . . . . . C19 C 0.5432(2) 0.8559(3) 0.42501(11) 0.0232(6) Uani 1 1 d . . . . . H19A H 0.582141 0.923541 0.451495 0.028 Uiso 1 1 calc R U . . . C20 C 0.4651(2) 0.7796(4) 0.43749(12) 0.0262(6) Uani 1 1 d . . . . . H20A H 0.451053 0.795249 0.472386 0.031 Uiso 1 1 calc R U . . . C21 C 0.4078(2) 0.6809(4) 0.39924(12) 0.0237(6) Uani 1 1 d . . . . . H21A H 0.354174 0.630242 0.408047 0.028 Uiso 1 1 calc R U . . . C22 C 0.42759(19) 0.6547(3) 0.34780(11) 0.0191(5) Uani 1 1 d . . . . . C23 C 0.3638(2) 0.5495(3) 0.30625(12) 0.0238(6) Uani 1 1 d . . . . . H23A H 0.388190 0.544614 0.272831 0.036 Uiso 1 1 calc R U . . . H23B H 0.363980 0.444638 0.321905 0.036 Uiso 1 1 calc R U . . . H23C H 0.297603 0.590577 0.296923 0.036 Uiso 1 1 calc R U . . . C24 C 0.6488(2) 0.9197(3) 0.36011(12) 0.0218(6) Uani 1 1 d . . . . . H24A H 0.653450 0.890765 0.322878 0.033 Uiso 1 1 calc R U . . . H24B H 0.638293 1.032421 0.361657 0.033 Uiso 1 1 calc R U . . . H24C H 0.708940 0.891433 0.386859 0.033 Uiso 1 1 calc R U . . . C25 C 0.69347(19) 0.5527(3) 0.40668(11) 0.0176(5) Uani 1 1 d . . . . . H25A H 0.629513 0.518555 0.405344 0.021 Uiso 1 1 calc R U . . . C26 C 0.8461(2) 0.6581(4) 0.45983(12) 0.0262(6) Uani 1 1 d . . . . . H26A H 0.874315 0.687129 0.498369 0.039 Uiso 1 1 calc R U . . . H26B H 0.885724 0.576611 0.448691 0.039 Uiso 1 1 calc R U . . . H26C H 0.844307 0.749811 0.436150 0.039 Uiso 1 1 calc R U . . . C27 C 0.7108(2) 0.5978(3) 0.50396(11) 0.0238(6) Uani 1 1 d . . . . . H27A H 0.760812 0.636583 0.535378 0.036 Uiso 1 1 calc R U . . . H27B H 0.653482 0.664763 0.498367 0.036 Uiso 1 1 calc R U . . . H27C H 0.693361 0.490883 0.511428 0.036 Uiso 1 1 calc R U . . . C28 C 0.1252(2) 0.8402(4) 0.51058(13) 0.0267(6) Uani 1 1 d . . . . . F1 F 0.10394(16) 0.6951(2) 0.52338(11) 0.0502(6) Uani 1 1 d . . . . . F2 F 0.04952(14) 0.8914(3) 0.47214(9) 0.0468(5) Uani 1 1 d . . . . . F3 F 0.13296(14) 0.9285(2) 0.55540(8) 0.0345(4) Uani 1 1 d . . . . . S1 S 0.23494(5) 0.84405(7) 0.48557(3) 0.01679(15) Uani 1 1 d . . . . . O3 O 0.24677(16) 1.0079(2) 0.47546(9) 0.0282(5) Uani 1 1 d . . . . . O4 O 0.20934(14) 0.7484(2) 0.43656(8) 0.0232(4) Uani 1 1 d . . . . . O5 O 0.30751(14) 0.7787(2) 0.53043(8) 0.0252(4) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0115(2) 0.0164(2) 0.0121(2) 0.00002(14) 0.00178(14) 0.00195(14) O1 0.0151(9) 0.0159(9) 0.0233(10) -0.0003(7) 0.0008(7) 0.0031(7) O2 0.0174(9) 0.0237(10) 0.0140(9) -0.0007(7) 0.0007(7) 0.0043(8) N1 0.0132(10) 0.0172(11) 0.0159(11) -0.0009(9) 0.0020(8) 0.0027(8) N2 0.0143(10) 0.0153(10) 0.0146(10) -0.0011(8) 0.0033(8) -0.0014(8) N3 0.0114(10) 0.0176(11) 0.0196(11) -0.0023(9) 0.0026(9) -0.0015(8) N4 0.0197(11) 0.0176(11) 0.0139(10) -0.0001(9) 0.0001(9) -0.0008(9) C1 0.0137(12) 0.0121(11) 0.0180(12) -0.0006(10) 0.0012(10) -0.0017(9) C2 0.0149(12) 0.0130(12) 0.0171(12) -0.0003(10) 0.0014(10) -0.0024(9) C3 0.0211(13) 0.0178(13) 0.0182(13) -0.0001(10) -0.0016(11) -0.0012(11) C4 0.0288(15) 0.0272(15) 0.0144(13) 0.0001(11) 0.0016(11) -0.0031(12) C5 0.0251(14) 0.0259(14) 0.0170(13) -0.0030(11) 0.0067(11) -0.0044(12) C6 0.0165(13) 0.0173(12) 0.0173(13) -0.0037(10) 0.0047(10) -0.0030(10) C7 0.0138(12) 0.0193(13) 0.0210(13) -0.0047(11) 0.0048(10) -0.0021(10) C8 0.0215(15) 0.0451(19) 0.0258(15) -0.0068(14) 0.0095(12) 0.0040(13) C9 0.0104(12) 0.0274(14) 0.0178(13) -0.0059(11) 0.0025(10) -0.0002(10) C10 0.0176(14) 0.0334(16) 0.0310(16) -0.0080(13) 0.0061(12) -0.0056(12) C11 0.0189(15) 0.048(2) 0.0373(18) -0.0098(16) -0.0001(13) -0.0126(14) C12 0.0149(14) 0.066(2) 0.0271(16) -0.0015(16) -0.0028(12) -0.0044(15) C13 0.0191(14) 0.0453(19) 0.0259(15) 0.0046(14) 0.0022(12) 0.0073(13) C14 0.0168(13) 0.0311(16) 0.0209(14) -0.0040(12) 0.0040(11) 0.0026(12) C15 0.0241(15) 0.0260(15) 0.0402(18) 0.0015(14) -0.0010(13) 0.0032(13) C16 0.0296(17) 0.0271(17) 0.064(2) -0.0060(16) 0.0052(16) -0.0108(14) C17 0.0154(12) 0.0176(12) 0.0159(12) 0.0023(10) 0.0031(10) 0.0060(10) C18 0.0168(13) 0.0190(13) 0.0191(13) 0.0004(10) 0.0026(10) 0.0065(10) C19 0.0240(14) 0.0261(15) 0.0179(13) -0.0033(11) 0.0017(11) 0.0070(12) C20 0.0277(15) 0.0339(16) 0.0180(14) 0.0039(12) 0.0077(11) 0.0120(13) C21 0.0201(14) 0.0297(15) 0.0231(14) 0.0079(12) 0.0087(11) 0.0059(12) C22 0.0151(12) 0.0193(13) 0.0222(14) 0.0040(11) 0.0035(10) 0.0052(10) C23 0.0182(13) 0.0234(14) 0.0283(15) 0.0024(12) 0.0026(11) -0.0010(11) C24 0.0196(13) 0.0204(14) 0.0243(14) -0.0043(11) 0.0035(11) -0.0001(11) C25 0.0176(13) 0.0143(12) 0.0188(13) 0.0005(10) 0.0004(10) 0.0020(10) C26 0.0215(14) 0.0287(15) 0.0249(15) 0.0002(12) -0.0014(11) -0.0052(12) C27 0.0315(16) 0.0235(14) 0.0162(13) 0.0010(11) 0.0055(11) 0.0020(12) C28 0.0230(14) 0.0250(15) 0.0341(16) -0.0036(13) 0.0110(12) -0.0005(12) F1 0.0490(13) 0.0308(11) 0.0852(17) -0.0012(11) 0.0439(12) -0.0112(9) F2 0.0216(9) 0.0635(14) 0.0510(13) -0.0143(11) 0.0006(9) 0.0147(9) F3 0.0366(10) 0.0392(11) 0.0326(10) -0.0068(8) 0.0179(8) 0.0030(8) S1 0.0163(3) 0.0175(3) 0.0164(3) -0.0012(2) 0.0039(2) -0.0014(2) O3 0.0386(12) 0.0190(10) 0.0295(11) 0.0021(9) 0.0130(9) -0.0044(9) O4 0.0220(10) 0.0262(10) 0.0198(10) -0.0065(8) 0.0020(8) 0.0014(8) O5 0.0213(10) 0.0303(11) 0.0208(10) -0.0011(8) -0.0011(8) 0.0022(8) 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' Cu Cu -1.9646 0.5888 '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' F F 0.0727 0.0534 '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 N2 Cu1 O2 164.57(9) . . ? N2 Cu1 N1 80.42(9) . . ? O2 Cu1 N1 104.71(8) . . ? N2 Cu1 N3 78.86(9) . . ? O2 Cu1 N3 91.88(8) . . ? N1 Cu1 N3 154.42(9) . . ? N2 Cu1 O1 93.62(8) . 2_645 ? O2 Cu1 O1 99.38(8) . 2_645 ? N1 Cu1 O1 102.14(8) . 2_645 ? N3 Cu1 O1 94.00(8) . 2_645 ? C1 O1 Cu1 145.21(17) . 2_655 ? C25 O2 Cu1 132.21(18) . . ? C1 N1 C17 120.8(2) . . ? C1 N1 Cu1 115.98(17) . . ? C17 N1 Cu1 123.20(16) . . ? C2 N2 C6 123.0(2) . . ? C2 N2 Cu1 118.00(18) . . ? C6 N2 Cu1 118.99(18) . . ? C7 N3 C9 121.4(2) . . ? C7 N3 Cu1 114.03(18) . . ? C9 N3 Cu1 124.06(17) . . ? C25 N4 C26 122.1(2) . . ? C25 N4 C27 120.6(2) . . ? C26 N4 C27 117.3(2) . . ? O1 C1 N1 128.4(2) . . ? O1 C1 C2 119.7(2) . . ? N1 C1 C2 111.9(2) . . ? N2 C2 C3 120.1(2) . . ? N2 C2 C1 113.3(2) . . ? C3 C2 C1 126.5(2) . . ? C4 C3 C2 118.1(3) . . ? C4 C3 H3A 120.9 . . ? C2 C3 H3A 120.9 . . ? C3 C4 C5 121.0(3) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C6 C5 C4 117.8(3) . . ? C6 C5 H5A 121.1 . . ? C4 C5 H5A 121.1 . . ? N2 C6 C5 119.9(2) . . ? N2 C6 C7 112.1(2) . . ? C5 C6 C7 127.6(2) . . ? N3 C7 C6 115.2(2) . . ? N3 C7 C8 126.2(3) . . ? C6 C7 C8 118.4(2) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 122.4(3) . . ? C14 C9 N3 120.5(2) . . ? C10 C9 N3 116.9(3) . . ? C11 C10 C9 117.9(3) . . ? C11 C10 C16 120.7(3) . . ? C9 C10 C16 121.3(3) . . ? C12 C11 C10 120.6(3) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C11 C12 C13 120.6(3) . . ? C11 C12 H12A 119.7 . . ? C13 C12 H12A 119.7 . . ? C12 C13 C14 120.9(3) . . ? C12 C13 H13A 119.6 . . ? C14 C13 H13A 119.6 . . ? C9 C14 C13 117.5(3) . . ? C9 C14 C15 121.3(3) . . ? C13 C14 C15 121.1(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 121.5(2) . . ? C18 C17 N1 118.1(2) . . ? C22 C17 N1 120.1(2) . . ? C19 C18 C17 118.4(3) . . ? C19 C18 C24 120.5(3) . . ? C17 C18 C24 121.1(2) . . ? C20 C19 C18 120.7(3) . . ? C20 C19 H19A 119.7 . . ? C18 C19 H19A 119.7 . . ? C21 C20 C19 120.2(3) . . ? C21 C20 H20A 119.9 . . ? C19 C20 H20A 119.9 . . ? C20 C21 C22 121.0(3) . . ? C20 C21 H21A 119.5 . . ? C22 C21 H21A 119.5 . . ? C21 C22 C17 118.2(3) . . ? C21 C22 C23 120.5(3) . . ? C17 C22 C23 121.3(2) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C18 C24 H24A 109.5 . . ? C18 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C18 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O2 C25 N4 123.2(3) . . ? O2 C25 H25A 118.4 . . ? N4 C25 H25A 118.4 . . ? N4 C26 H26A 109.5 . . ? N4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N4 C27 H27A 109.5 . . ? N4 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N4 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? F2 C28 F3 107.8(2) . . ? F2 C28 F1 106.8(3) . . ? F3 C28 F1 107.8(3) . . ? F2 C28 S1 111.0(2) . . ? F3 C28 S1 112.0(2) . . ? F1 C28 S1 111.2(2) . . ? O5 S1 O4 115.05(12) . . ? O5 S1 O3 114.98(13) . . ? O4 S1 O3 114.84(13) . . ? O5 S1 C28 103.89(14) . . ? O4 S1 C28 102.71(13) . . ? O3 S1 C28 102.95(14) . . ? 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 Cu1 N2 1.918(2) . ? Cu1 O2 1.9233(18) . ? Cu1 N1 1.998(2) . ? Cu1 N3 2.078(2) . ? Cu1 O1 2.2762(18) 2_645 ? O1 C1 1.253(3) . ? O2 C25 1.255(3) . ? N1 C1 1.332(3) . ? N1 C17 1.426(3) . ? N2 C2 1.327(3) . ? N2 C6 1.339(3) . ? N3 C7 1.282(4) . ? N3 C9 1.438(3) . ? N4 C25 1.314(3) . ? N4 C26 1.461(4) . ? N4 C27 1.461(4) . ? C1 C2 1.509(4) . ? C2 C3 1.388(4) . ? C3 C4 1.384(4) . ? C3 H3A 0.9500 . ? C4 C5 1.394(4) . ? C4 H4A 0.9500 . ? C5 C6 1.388(4) . ? C5 H5A 0.9500 . ? C6 C7 1.491(4) . ? C7 C8 1.495(4) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.394(4) . ? C9 C10 1.399(4) . ? C10 C11 1.391(4) . ? C10 C16 1.508(5) . ? C11 C12 1.379(5) . ? C11 H11A 0.9500 . ? C12 C13 1.380(5) . ? C12 H12A 0.9500 . ? C13 C14 1.397(4) . ? C13 H13A 0.9500 . ? C14 C15 1.496(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.403(4) . ? C17 C22 1.404(4) . ? C18 C19 1.398(4) . ? C18 C24 1.510(4) . ? C19 C20 1.390(4) . ? C19 H19A 0.9500 . ? C20 C21 1.384(4) . ? C20 H20A 0.9500 . ? C21 C22 1.399(4) . ? C21 H21A 0.9500 . ? C22 C23 1.502(4) . ? 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 0.9500 . ? 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 F2 1.331(4) . ? C28 F3 1.333(4) . ? C28 F1 1.337(4) . ? C28 S1 1.820(3) . ? S1 O5 1.440(2) . ? S1 O4 1.444(2) . ? S1 O3 1.444(2) . ? 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 Cu1 O1 C1 N1 91.8(4) 2_655 . . . ? Cu1 O1 C1 C2 -85.8(3) 2_655 . . . ? C17 N1 C1 O1 0.9(4) . . . . ? Cu1 N1 C1 O1 179.2(2) . . . . ? C17 N1 C1 C2 178.6(2) . . . . ? Cu1 N1 C1 C2 -3.1(3) . . . . ? C6 N2 C2 C3 2.6(4) . . . . ? Cu1 N2 C2 C3 -177.59(19) . . . . ? C6 N2 C2 C1 -173.1(2) . . . . ? Cu1 N2 C2 C1 6.7(3) . . . . ? O1 C1 C2 N2 175.8(2) . . . . ? N1 C1 C2 N2 -2.1(3) . . . . ? O1 C1 C2 C3 0.4(4) . . . . ? N1 C1 C2 C3 -177.5(2) . . . . ? N2 C2 C3 C4 -1.8(4) . . . . ? C1 C2 C3 C4 173.4(3) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? C2 N2 C6 C5 -1.5(4) . . . . ? Cu1 N2 C6 C5 178.8(2) . . . . ? C2 N2 C6 C7 172.2(2) . . . . ? Cu1 N2 C6 C7 -7.6(3) . . . . ? C4 C5 C6 N2 -0.5(4) . . . . ? C4 C5 C6 C7 -173.1(3) . . . . ? C9 N3 C7 C6 -166.0(2) . . . . ? Cu1 N3 C7 C6 5.8(3) . . . . ? C9 N3 C7 C8 9.0(4) . . . . ? Cu1 N3 C7 C8 -179.2(2) . . . . ? N2 C6 C7 N3 0.6(3) . . . . ? C5 C6 C7 N3 173.7(3) . . . . ? N2 C6 C7 C8 -174.8(3) . . . . ? C5 C6 C7 C8 -1.8(4) . . . . ? C7 N3 C9 C14 -103.5(3) . . . . ? Cu1 N3 C9 C14 85.5(3) . . . . ? C7 N3 C9 C10 82.0(3) . . . . ? Cu1 N3 C9 C10 -89.0(3) . . . . ? C14 C9 C10 C11 1.6(4) . . . . ? N3 C9 C10 C11 176.0(3) . . . . ? C14 C9 C10 C16 -176.4(3) . . . . ? N3 C9 C10 C16 -2.0(4) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? C16 C10 C11 C12 178.1(3) . . . . ? C10 C11 C12 C13 -1.1(5) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? C10 C9 C14 C13 -2.2(4) . . . . ? N3 C9 C14 C13 -176.4(3) . . . . ? C10 C9 C14 C15 178.0(3) . . . . ? N3 C9 C14 C15 3.8(4) . . . . ? C12 C13 C14 C9 1.1(4) . . . . ? C12 C13 C14 C15 -179.1(3) . . . . ? C1 N1 C17 C18 -112.7(3) . . . . ? Cu1 N1 C17 C18 69.2(3) . . . . ? C1 N1 C17 C22 73.3(3) . . . . ? Cu1 N1 C17 C22 -104.9(2) . . . . ? C22 C17 C18 C19 1.6(4) . . . . ? N1 C17 C18 C19 -172.3(2) . . . . ? C22 C17 C18 C24 -178.3(2) . . . . ? N1 C17 C18 C24 7.8(4) . . . . ? C17 C18 C19 C20 -1.1(4) . . . . ? C24 C18 C19 C20 178.9(3) . . . . ? C18 C19 C20 C21 -0.1(4) . . . . ? C19 C20 C21 C22 0.7(4) . . . . ? C20 C21 C22 C17 -0.1(4) . . . . ? C20 C21 C22 C23 -178.9(3) . . . . ? C18 C17 C22 C21 -1.0(4) . . . . ? N1 C17 C22 C21 172.8(2) . . . . ? C18 C17 C22 C23 177.8(2) . . . . ? N1 C17 C22 C23 -8.4(4) . . . . ? Cu1 O2 C25 N4 -152.8(2) . . . . ? C26 N4 C25 O2 1.6(4) . . . . ? C27 N4 C25 O2 -179.4(2) . . . . ? F2 C28 S1 O5 -177.2(2) . . . . ? F3 C28 S1 O5 62.2(2) . . . . ? F1 C28 S1 O5 -58.4(3) . . . . ? F2 C28 S1 O4 -57.0(2) . . . . ? F3 C28 S1 O4 -177.6(2) . . . . ? F1 C28 S1 O4 61.8(3) . . . . ? F2 C28 S1 O3 62.6(2) . . . . ? F3 C28 S1 O3 -58.0(2) . . . . ? F1 C28 S1 O3 -178.6(2) . . . . ?