#------------------------------------------------------------------------------ #$Date: 2020-10-06 12:01:12 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257559 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/51/7705174.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_7705174 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 'C25 H29 Cu N5 O2' _chemical_formula_sum 'C25 H29 Cu N5 O2' _chemical_formula_weight 495.07 _chemical_name_common '[Cu(Py(O=C-N)2(PhMe2)2(EDA)]' _space_group_crystal_system tetragonal _space_group_IT_number 114 _space_group_name_Hall 'P -4 2n' _space_group_name_H-M_alt 'P -4 21 c' _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 23.87663(17) _cell_length_b 23.87663(17) _cell_length_c 7.93792(8) _cell_measurement_reflns_used 11190 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 76.3020 _cell_measurement_theta_min 4.1240 _cell_volume 4525.36(6) _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 1.000 _diffrn_measured_fraction_theta_max 0.997 _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 0.0333 _diffrn_reflns_av_unetI/netI 0.0269 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 18764 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.968 _diffrn_reflns_theta_min 3.702 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.628 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84949 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; 'Wed Jul 09 14:57:10 2014' ; _exptl_crystal_colour dark-green _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_description column _exptl_crystal_F_000 2072 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.415 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.059 _refine_ls_abs_structure_details ; Flack x determined using 1891 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.028(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 298 _refine_ls_number_reflns 4607 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0301 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+1.3621P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.0812 _reflns_Friedel_coverage 0.769 _reflns_Friedel_fraction_full 0.989 _reflns_Friedel_fraction_max 0.983 _reflns_number_gt 4446 _reflns_number_total 4607 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02288h2.cif _cod_data_source_block Complex3a _cod_depositor_comments 'Adding full bibliography for 7705173--7705180.cif.' _cod_original_cell_volume 4525.36(8) _cod_database_code 7705174 _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 0.758 _shelx_estimated_absorpt_t_max 0.881 _shelx_res_file ; TITL DH78-2 in P-421c #114 full.res created by SHELXL-2018/3 at 11:56:04 on 20-Jul-2020 CELL 1.54184 23.87663 23.87663 7.93792 90 90 90 ZERR 8 0.00017 0.00017 0.00008 0 0 0 LATT -1 SYMM +Y,-X,-Z SYMM -X,-Y,+Z SYMM -Y,+X,-Z SYMM 0.5+X,0.5-Y,0.5-Z SYMM 0.5-X,0.5+Y,0.5-Z SYMM 0.5-Y,0.5-X,0.5+Z SYMM 0.5+Y,0.5+X,0.5+Z SFAC C H Cu N O UNIT 200 232 8 40 16 TEMP -173 SIZE 0.18 0.110 0.08 REM column dark-green OMIT 0 150 L.S. 4 PLAN 6 BOND $H CONF fmap 2 acta WGHT 0.054300 1.362100 FVAR 4.13696 CU1 3 0.437711 0.742251 0.601709 11.00000 0.00861 0.00990 = 0.01169 -0.00131 0.00115 -0.00057 O1 5 0.402210 0.839785 1.016669 11.00000 0.01570 0.01551 = 0.01437 -0.00466 0.00020 0.00008 O2 5 0.319763 0.622070 0.483372 11.00000 0.01580 0.01104 = 0.02031 -0.00253 0.00034 -0.00391 C1 1 0.406639 0.808104 0.893358 11.00000 0.01041 0.01033 = 0.01436 0.00133 -0.00097 -0.00052 C2 1 0.355690 0.775401 0.836656 11.00000 0.01264 0.01036 = 0.01036 -0.00022 -0.00021 0.00072 C3 1 0.302091 0.780055 0.902006 11.00000 0.01498 0.01315 = 0.01366 -0.00118 0.00143 0.00049 AFIX 43 H3A 2 0.293419 0.808046 0.982961 11.00000 -1.20000 AFIX 0 C4 1 0.260998 0.742604 0.846115 11.00000 0.01003 0.01722 = 0.01547 0.00196 0.00089 -0.00019 AFIX 43 H4A 2 0.223642 0.745801 0.886177 11.00000 -1.20000 AFIX 0 C5 1 0.274966 0.700608 0.731579 11.00000 0.01236 0.01305 = 0.01355 0.00315 -0.00049 -0.00154 AFIX 43 H5A 2 0.248179 0.673321 0.698495 11.00000 -1.20000 AFIX 0 C6 1 0.329112 0.699659 0.666945 11.00000 0.01172 0.00952 = 0.01188 0.00087 -0.00074 -0.00027 C7 1 0.350833 0.660602 0.533119 11.00000 0.01228 0.00999 = 0.01211 0.00076 0.00028 0.00135 C8 1 0.428335 0.645605 0.348394 11.00000 0.01244 0.00975 = 0.01460 -0.00131 0.00322 -0.00150 C9 1 0.405512 0.649623 0.184931 11.00000 0.01679 0.01101 = 0.01525 -0.00093 -0.00071 -0.00337 C10 1 0.434230 0.625948 0.050672 11.00000 0.02172 0.01536 = 0.01546 -0.00187 0.00039 -0.00253 AFIX 43 H10A 2 0.418763 0.628133 -0.059398 11.00000 -1.20000 AFIX 0 C11 1 0.485213 0.599112 0.074598 11.00000 0.02165 0.01519 = 0.02154 -0.00312 0.00653 0.00141 AFIX 43 H11A 2 0.504853 0.583622 -0.018474 11.00000 -1.20000 AFIX 0 C12 1 0.507093 0.595197 0.235820 11.00000 0.01613 0.01582 = 0.02192 0.00054 0.00426 0.00120 AFIX 43 H12A 2 0.542020 0.576919 0.252050 11.00000 -1.20000 AFIX 0 C13 1 0.479141 0.617411 0.374930 11.00000 0.01359 0.01108 = 0.01779 0.00009 0.00247 -0.00135 C14 1 0.502194 0.607580 0.549255 11.00000 0.01473 0.01641 = 0.02313 0.00142 -0.00022 0.00042 AFIX 33 H14A 2 0.477916 0.625768 0.632419 11.00000 -1.50000 H14B 2 0.503640 0.567251 0.571784 11.00000 -1.50000 H14C 2 0.540011 0.623331 0.556880 11.00000 -1.50000 AFIX 0 C15 1 0.351157 0.679566 0.153429 11.00000 0.02058 0.01648 = 0.01455 -0.00109 -0.00277 0.00137 AFIX 33 H15A 2 0.336293 0.693765 0.260288 11.00000 -1.50000 H15B 2 0.357548 0.710944 0.076204 11.00000 -1.50000 H15C 2 0.324180 0.653516 0.103251 11.00000 -1.50000 AFIX 0 C16 1 0.503693 0.820946 0.843427 11.00000 0.01307 0.01628 = 0.01186 -0.00233 -0.00009 -0.00114 C17 1 0.511716 0.879142 0.824615 11.00000 0.01579 0.01650 = 0.01805 -0.00178 0.00016 -0.00329 C18 1 0.564251 0.901812 0.861512 11.00000 0.02270 0.01842 = 0.03264 -0.00098 -0.00177 -0.01013 AFIX 43 H18A 2 0.570163 0.940911 0.848262 11.00000 -1.20000 AFIX 0 C19 1 0.607804 0.868369 0.916970 11.00000 0.01626 0.03049 = 0.03918 -0.00048 -0.00733 -0.01067 AFIX 43 H19A 2 0.642954 0.884671 0.944171 11.00000 -1.20000 AFIX 0 C20 1 0.600149 0.810985 0.932879 11.00000 0.01403 0.02807 = 0.02522 0.00184 -0.00452 -0.00114 AFIX 43 H20A 2 0.630481 0.788118 0.968493 11.00000 -1.20000 AFIX 0 C21 1 0.548273 0.786404 0.897077 11.00000 0.01380 0.02017 = 0.01459 0.00069 -0.00131 -0.00073 C22 1 0.540719 0.724223 0.918514 11.00000 0.01731 0.01887 = 0.01941 0.00076 -0.00300 0.00265 AFIX 33 H22A 2 0.502282 0.713875 0.888411 11.00000 -1.50000 H22B 2 0.567040 0.704354 0.845017 11.00000 -1.50000 H22C 2 0.547916 0.713957 1.036072 11.00000 -1.50000 AFIX 0 C23 1 0.465317 0.917432 0.766719 11.00000 0.02285 0.01214 = 0.02795 -0.00003 -0.00249 -0.00167 AFIX 33 H23A 2 0.431367 0.895411 0.746074 11.00000 -1.50000 H23B 2 0.457802 0.945477 0.853981 11.00000 -1.50000 H23C 2 0.476631 0.936290 0.662478 11.00000 -1.50000 AFIX 0 C24 1 0.480797 0.826749 0.353865 11.00000 0.01607 0.01536 = 0.01631 0.00327 -0.00053 -0.00349 AFIX 23 H24A 2 0.497661 0.851844 0.439209 11.00000 -1.20000 H24B 2 0.480051 0.846726 0.244600 11.00000 -1.20000 AFIX 0 C25 1 0.515177 0.773516 0.338384 11.00000 0.01409 0.01954 = 0.01234 -0.00046 0.00309 -0.00166 AFIX 23 H25A 2 0.498597 0.748687 0.251841 11.00000 -1.20000 H25B 2 0.553929 0.782752 0.303802 11.00000 -1.20000 AFIX 0 N1 4 0.451737 0.795460 0.801258 11.00000 0.01199 0.01287 = 0.01285 -0.00328 0.00027 -0.00147 N2 4 0.366625 0.737252 0.718955 11.00000 0.01087 0.00936 = 0.01254 0.00001 -0.00138 -0.00002 N3 4 0.402816 0.674154 0.485065 11.00000 0.01161 0.01034 = 0.01270 -0.00216 0.00037 -0.00010 N4 4 0.515679 0.744714 0.504390 11.00000 0.01114 0.01304 = 0.01504 -0.00143 0.00160 0.00089 AFIX 23 H4B 2 0.538865 0.763259 0.576270 11.00000 -1.20000 H4C 2 0.528907 0.709221 0.491716 11.00000 -1.20000 AFIX 0 N5 4 0.423261 0.811324 0.404640 11.00000 0.01282 0.01325 = 0.01543 0.00135 -0.00093 0.00022 AFIX 23 H5B 2 0.403270 0.798185 0.315396 11.00000 -1.20000 H5C 2 0.404931 0.841086 0.450341 11.00000 -1.20000 AFIX 0 HKLF 4 REM DH78-2 in P-421c #114 REM wR2 = 0.0812, GooF = S = 1.046, Restrained GooF = 1.046 for all data REM R1 = 0.0301 for 4446 Fo > 4sig(Fo) and 0.0319 for all 4607 data REM 298 parameters refined using 0 restraints END WGHT 0.0545 1.3550 REM Highest difference peak 0.415, deepest hole -0.455, 1-sigma level 0.059 Q1 1 0.3194 0.6610 0.2076 11.00000 0.05 0.42 Q2 1 0.3531 0.7168 0.1918 11.00000 0.05 0.38 Q3 1 0.3424 0.6764 0.0274 11.00000 0.05 0.37 Q4 1 0.4366 0.9238 0.8715 11.00000 0.05 0.35 Q5 1 0.4416 0.8984 0.6741 11.00000 0.05 0.29 Q6 1 0.4800 0.9591 0.7315 11.00000 0.05 0.25 ; _shelx_res_checksum 10767 loop_ _space_group_symop_operation_xyz 'x, y, z' 'y, -x, -z' '-x, -y, z' '-y, x, -z' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+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 0.43771(2) 0.74225(2) 0.60171(5) 0.01007(11) Uani 1 1 d . . . . . O1 O 0.40221(9) 0.83978(8) 1.0167(3) 0.0152(4) Uani 1 1 d . . . . . O2 O 0.31976(9) 0.62207(8) 0.4834(3) 0.0157(4) Uani 1 1 d . . . . . C1 C 0.40664(11) 0.80810(10) 0.8934(4) 0.0117(5) Uani 1 1 d . . . . . C2 C 0.35569(12) 0.77540(11) 0.8367(3) 0.0111(5) Uani 1 1 d . . . . . C3 C 0.30209(11) 0.78006(11) 0.9020(4) 0.0139(5) Uani 1 1 d . . . . . H3A H 0.293419 0.808046 0.982961 0.017 Uiso 1 1 calc R U . . . C4 C 0.26100(11) 0.74260(12) 0.8461(3) 0.0142(5) Uani 1 1 d . . . . . H4A H 0.223642 0.745801 0.886177 0.017 Uiso 1 1 calc R U . . . C5 C 0.27497(12) 0.70061(12) 0.7316(4) 0.0130(5) Uani 1 1 d . . . . . H5A H 0.248179 0.673321 0.698495 0.016 Uiso 1 1 calc R U . . . C6 C 0.32911(11) 0.69966(11) 0.6669(3) 0.0110(5) Uani 1 1 d . . . . . C7 C 0.35083(12) 0.66060(11) 0.5331(3) 0.0115(5) Uani 1 1 d . . . . . C8 C 0.42834(11) 0.64560(11) 0.3484(3) 0.0123(5) Uani 1 1 d . . . . . C9 C 0.40551(12) 0.64962(11) 0.1849(4) 0.0143(5) Uani 1 1 d . . . . . C10 C 0.43423(13) 0.62595(12) 0.0507(4) 0.0175(6) Uani 1 1 d . . . . . H10A H 0.418763 0.628133 -0.059398 0.021 Uiso 1 1 calc R U . . . C11 C 0.48521(13) 0.59911(12) 0.0746(4) 0.0195(6) Uani 1 1 d . . . . . H11A H 0.504853 0.583622 -0.018474 0.023 Uiso 1 1 calc R U . . . C12 C 0.50709(13) 0.59520(12) 0.2358(4) 0.0180(6) Uani 1 1 d . . . . . H12A H 0.542020 0.576919 0.252050 0.022 Uiso 1 1 calc R U . . . C13 C 0.47914(12) 0.61741(11) 0.3749(4) 0.0142(5) Uani 1 1 d . . . . . C14 C 0.50219(12) 0.60758(13) 0.5493(4) 0.0181(6) Uani 1 1 d . . . . . H14A H 0.477916 0.625768 0.632419 0.027 Uiso 1 1 calc R U . . . H14B H 0.503640 0.567251 0.571784 0.027 Uiso 1 1 calc R U . . . H14C H 0.540011 0.623331 0.556880 0.027 Uiso 1 1 calc R U . . . C15 C 0.35116(13) 0.67957(13) 0.1534(4) 0.0172(6) Uani 1 1 d . . . . . H15A H 0.336293 0.693765 0.260288 0.026 Uiso 1 1 calc R U . . . H15B H 0.357548 0.710944 0.076204 0.026 Uiso 1 1 calc R U . . . H15C H 0.324180 0.653516 0.103251 0.026 Uiso 1 1 calc R U . . . C16 C 0.50369(12) 0.82095(12) 0.8434(3) 0.0137(5) Uani 1 1 d . . . . . C17 C 0.51172(12) 0.87914(13) 0.8246(4) 0.0168(6) Uani 1 1 d . . . . . C18 C 0.56425(14) 0.90181(14) 0.8615(4) 0.0246(7) Uani 1 1 d . . . . . H18A H 0.570163 0.940911 0.848262 0.030 Uiso 1 1 calc R U . . . C19 C 0.60780(13) 0.86837(14) 0.9170(5) 0.0286(7) Uani 1 1 d . . . . . H19A H 0.642954 0.884671 0.944171 0.034 Uiso 1 1 calc R U . . . C20 C 0.60015(13) 0.81098(14) 0.9329(4) 0.0224(6) Uani 1 1 d . . . . . H20A H 0.630481 0.788118 0.968493 0.027 Uiso 1 1 calc R U . . . C21 C 0.54827(12) 0.78640(12) 0.8971(4) 0.0162(5) Uani 1 1 d . . . . . C22 C 0.54072(12) 0.72422(12) 0.9185(4) 0.0185(6) Uani 1 1 d . . . . . H22A H 0.502282 0.713875 0.888411 0.028 Uiso 1 1 calc R U . . . H22B H 0.567040 0.704354 0.845017 0.028 Uiso 1 1 calc R U . . . H22C H 0.547916 0.713957 1.036072 0.028 Uiso 1 1 calc R U . . . C23 C 0.46532(13) 0.91743(12) 0.7667(4) 0.0210(6) Uani 1 1 d . . . . . H23A H 0.431367 0.895411 0.746074 0.031 Uiso 1 1 calc R U . . . H23B H 0.457802 0.945477 0.853981 0.031 Uiso 1 1 calc R U . . . H23C H 0.476631 0.936290 0.662478 0.031 Uiso 1 1 calc R U . . . C24 C 0.48080(12) 0.82675(12) 0.3539(4) 0.0159(6) Uani 1 1 d . . . . . H24A H 0.497661 0.851844 0.439209 0.019 Uiso 1 1 calc R U . . . H24B H 0.480051 0.846726 0.244600 0.019 Uiso 1 1 calc R U . . . C25 C 0.51518(12) 0.77352(12) 0.3384(4) 0.0153(5) Uani 1 1 d . . . . . H25A H 0.498597 0.748687 0.251841 0.018 Uiso 1 1 calc R U . . . H25B H 0.553929 0.782752 0.303802 0.018 Uiso 1 1 calc R U . . . N1 N 0.45174(10) 0.79546(10) 0.8013(3) 0.0126(4) Uani 1 1 d . . . . . N2 N 0.36663(9) 0.73725(10) 0.7190(3) 0.0109(4) Uani 1 1 d . . . . . N3 N 0.40282(10) 0.67415(10) 0.4851(3) 0.0116(4) Uani 1 1 d . . . . . N4 N 0.51568(9) 0.74471(10) 0.5044(3) 0.0131(4) Uani 1 1 d . . . . . H4B H 0.538865 0.763259 0.576270 0.016 Uiso 1 1 calc R U . . . H4C H 0.528907 0.709221 0.491716 0.016 Uiso 1 1 calc R U . . . N5 N 0.42326(9) 0.81132(9) 0.4046(3) 0.0138(4) Uani 1 1 d . . . . . H5B H 0.403270 0.798185 0.315396 0.017 Uiso 1 1 calc R U . . . H5C H 0.404931 0.841086 0.450341 0.017 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 Cu1 0.00861(18) 0.00990(18) 0.01169(18) -0.00131(15) 0.00115(15) -0.00057(13) O1 0.0157(9) 0.0155(9) 0.0144(9) -0.0047(7) 0.0002(8) 0.0001(7) O2 0.0158(9) 0.0110(9) 0.0203(10) -0.0025(8) 0.0003(8) -0.0039(8) C1 0.0104(11) 0.0103(11) 0.0144(11) 0.0013(10) -0.0010(11) -0.0005(9) C2 0.0126(12) 0.0104(11) 0.0104(11) -0.0002(9) -0.0002(10) 0.0007(9) C3 0.0150(12) 0.0131(11) 0.0137(12) -0.0012(11) 0.0014(11) 0.0005(10) C4 0.0100(11) 0.0172(12) 0.0155(12) 0.0020(10) 0.0009(10) -0.0002(10) C5 0.0124(12) 0.0130(12) 0.0135(12) 0.0031(10) -0.0005(9) -0.0015(10) C6 0.0117(12) 0.0095(11) 0.0119(11) 0.0009(10) -0.0007(10) -0.0003(10) C7 0.0123(12) 0.0100(12) 0.0121(11) 0.0008(9) 0.0003(10) 0.0014(10) C8 0.0124(12) 0.0097(11) 0.0146(12) -0.0013(9) 0.0032(9) -0.0015(10) C9 0.0168(13) 0.0110(12) 0.0153(13) -0.0009(10) -0.0007(11) -0.0034(11) C10 0.0217(14) 0.0154(12) 0.0155(13) -0.0019(10) 0.0004(11) -0.0025(10) C11 0.0216(14) 0.0152(12) 0.0215(15) -0.0031(11) 0.0065(12) 0.0014(11) C12 0.0161(13) 0.0158(13) 0.0219(14) 0.0005(11) 0.0043(11) 0.0012(11) C13 0.0136(12) 0.0111(11) 0.0178(14) 0.0001(10) 0.0025(11) -0.0014(10) C14 0.0147(13) 0.0164(13) 0.0231(15) 0.0014(11) -0.0002(11) 0.0004(10) C15 0.0206(14) 0.0165(13) 0.0146(12) -0.0011(10) -0.0028(11) 0.0014(11) C16 0.0131(12) 0.0163(13) 0.0119(11) -0.0023(10) -0.0001(9) -0.0011(11) C17 0.0158(13) 0.0165(13) 0.0180(13) -0.0018(11) 0.0002(11) -0.0033(11) C18 0.0227(15) 0.0184(14) 0.0326(17) -0.0010(12) -0.0018(13) -0.0101(12) C19 0.0163(14) 0.0305(17) 0.039(2) -0.0005(15) -0.0073(14) -0.0107(12) C20 0.0140(13) 0.0281(16) 0.0252(16) 0.0018(12) -0.0045(12) -0.0011(11) C21 0.0138(12) 0.0202(13) 0.0146(11) 0.0007(11) -0.0013(11) -0.0007(10) C22 0.0173(12) 0.0189(13) 0.0194(14) 0.0008(11) -0.0030(11) 0.0027(10) C23 0.0228(15) 0.0121(12) 0.0280(15) 0.0000(11) -0.0025(12) -0.0017(11) C24 0.0161(13) 0.0154(13) 0.0163(13) 0.0033(10) -0.0005(10) -0.0035(11) C25 0.0141(13) 0.0195(14) 0.0123(11) -0.0005(10) 0.0031(10) -0.0017(10) N1 0.0120(11) 0.0129(10) 0.0128(10) -0.0033(8) 0.0003(9) -0.0015(8) N2 0.0109(10) 0.0094(10) 0.0125(10) 0.0000(9) -0.0014(8) 0.0000(8) N3 0.0116(10) 0.0103(10) 0.0127(10) -0.0022(8) 0.0004(8) -0.0001(8) N4 0.0111(10) 0.0130(10) 0.0150(10) -0.0014(9) 0.0016(8) 0.0009(8) N5 0.0128(10) 0.0133(10) 0.0154(10) 0.0014(9) -0.0009(9) 0.0002(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' 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 N4 173.53(10) . . ? N2 Cu1 N3 79.17(10) . . ? N4 Cu1 N3 103.03(10) . . ? N2 Cu1 N1 79.11(10) . . ? N4 Cu1 N1 97.28(9) . . ? N3 Cu1 N1 154.72(10) . . ? N2 Cu1 N5 103.85(9) . . ? N4 Cu1 N5 81.78(9) . . ? N3 Cu1 N5 101.58(9) . . ? N1 Cu1 N5 96.04(9) . . ? O1 C1 N1 129.6(2) . . ? O1 C1 C2 118.7(2) . . ? N1 C1 C2 111.6(2) . . ? N2 C2 C3 119.9(3) . . ? N2 C2 C1 113.8(2) . . ? C3 C2 C1 126.1(2) . . ? C2 C3 C4 118.5(3) . . ? C2 C3 H3A 120.7 . . ? C4 C3 H3A 120.7 . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C6 C5 C4 118.3(3) . . ? C6 C5 H5A 120.8 . . ? C4 C5 H5A 120.8 . . ? N2 C6 C5 119.9(3) . . ? N2 C6 C7 113.8(2) . . ? C5 C6 C7 126.2(3) . . ? O2 C7 N3 129.8(3) . . ? O2 C7 C6 118.4(2) . . ? N3 C7 C6 111.8(2) . . ? C13 C8 C9 120.3(3) . . ? C13 C8 N3 119.1(3) . . ? C9 C8 N3 120.3(2) . . ? C10 C9 C8 119.2(3) . . ? C10 C9 C15 119.5(3) . . ? C8 C9 C15 121.3(3) . . ? C9 C10 C11 121.1(3) . . ? C9 C10 H10A 119.5 . . ? C11 C10 H10A 119.5 . . ? C12 C11 C10 119.2(3) . . ? C12 C11 H11A 120.4 . . ? C10 C11 H11A 120.4 . . ? C11 C12 C13 121.7(3) . . ? C11 C12 H12A 119.2 . . ? C13 C12 H12A 119.2 . . ? C12 C13 C8 118.5(3) . . ? C12 C13 C14 119.5(3) . . ? C8 C13 C14 121.9(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C9 C15 H15A 109.5 . . ? C9 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C9 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 120.3(3) . . ? C17 C16 N1 121.0(3) . . ? C21 C16 N1 118.6(3) . . ? C18 C17 C16 118.8(3) . . ? C18 C17 C23 119.2(3) . . ? C16 C17 C23 122.0(3) . . ? C19 C18 C17 121.2(3) . . ? C19 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? C18 C19 C20 120.0(3) . . ? C18 C19 H19A 120.0 . . ? C20 C19 H19A 120.0 . . ? C19 C20 C21 120.8(3) . . ? C19 C20 H20A 119.6 . . ? C21 C20 H20A 119.6 . . ? C20 C21 C16 118.9(3) . . ? C20 C21 C22 119.8(3) . . ? C16 C21 C22 121.3(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17 C23 H23A 109.5 . . ? C17 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C17 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N5 C24 C25 108.4(2) . . ? N5 C24 H24A 110.0 . . ? C25 C24 H24A 110.0 . . ? N5 C24 H24B 110.0 . . ? C25 C24 H24B 110.0 . . ? H24A C24 H24B 108.4 . . ? N4 C25 C24 108.7(2) . . ? N4 C25 H25A 110.0 . . ? C24 C25 H25A 110.0 . . ? N4 C25 H25B 110.0 . . ? C24 C25 H25B 110.0 . . ? H25A C25 H25B 108.3 . . ? C1 N1 C16 118.5(2) . . ? C1 N1 Cu1 115.44(18) . . ? C16 N1 Cu1 125.98(18) . . ? C2 N2 C6 123.1(2) . . ? C2 N2 Cu1 117.81(19) . . ? C6 N2 Cu1 118.73(19) . . ? C7 N3 C8 120.0(2) . . ? C7 N3 Cu1 116.13(18) . . ? C8 N3 Cu1 123.53(18) . . ? C25 N4 Cu1 110.22(17) . . ? C25 N4 H4B 109.6 . . ? Cu1 N4 H4B 109.6 . . ? C25 N4 H4C 109.6 . . ? Cu1 N4 H4C 109.6 . . ? H4B N4 H4C 108.1 . . ? C24 N5 Cu1 102.99(16) . . ? C24 N5 H5B 111.2 . . ? Cu1 N5 H5B 111.2 . . ? C24 N5 H5C 111.2 . . ? Cu1 N5 H5C 111.2 . . ? H5B N5 H5C 109.1 . . ? 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 1.939(2) . ? Cu1 N4 2.016(2) . ? Cu1 N3 2.048(2) . ? Cu1 N1 2.058(2) . ? Cu1 N5 2.299(2) . ? O1 C1 1.242(4) . ? O2 C7 1.246(4) . ? C1 N1 1.336(4) . ? C1 C2 1.514(4) . ? C2 N2 1.331(4) . ? C2 C3 1.385(4) . ? C3 C4 1.400(4) . ? C3 H3A 0.9500 . ? C4 C5 1.394(4) . ? C4 H4A 0.9500 . ? C5 C6 1.391(4) . ? C5 H5A 0.9500 . ? C6 N2 1.334(4) . ? C6 C7 1.506(4) . ? C7 N3 1.338(4) . ? C8 C13 1.403(4) . ? C8 C9 1.411(4) . ? C8 N3 1.419(3) . ? C9 C10 1.388(4) . ? C9 C15 1.503(4) . ? C10 C11 1.389(4) . ? C10 H10A 0.9500 . ? C11 C12 1.385(4) . ? C11 H11A 0.9500 . ? C12 C13 1.395(4) . ? C12 H12A 0.9500 . ? C13 C14 1.508(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.411(4) . ? C16 C21 1.412(4) . ? C16 N1 1.422(4) . ? C17 C18 1.397(4) . ? C17 C23 1.508(4) . ? C18 C19 1.383(5) . ? C18 H18A 0.9500 . ? C19 C20 1.388(5) . ? C19 H19A 0.9500 . ? C20 C21 1.400(4) . ? C20 H20A 0.9500 . ? C21 C22 1.505(4) . ? 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 N5 1.478(3) . ? C24 C25 1.518(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N4 1.486(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N4 H4B 0.9100 . ? N4 H4C 0.9100 . ? N5 H5B 0.9100 . ? N5 H5C 0.9100 . ? 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 O1 C1 C2 N2 -171.4(2) . . . . ? N1 C1 C2 N2 5.9(3) . . . . ? O1 C1 C2 C3 5.0(4) . . . . ? N1 C1 C2 C3 -177.7(3) . . . . ? N2 C2 C3 C4 2.4(4) . . . . ? C1 C2 C3 C4 -173.7(3) . . . . ? C2 C3 C4 C5 2.2(4) . . . . ? C3 C4 C5 C6 -4.4(4) . . . . ? C4 C5 C6 N2 2.1(4) . . . . ? C4 C5 C6 C7 -175.1(3) . . . . ? N2 C6 C7 O2 176.1(2) . . . . ? C5 C6 C7 O2 -6.5(4) . . . . ? N2 C6 C7 N3 -4.2(3) . . . . ? C5 C6 C7 N3 173.2(3) . . . . ? C13 C8 C9 C10 -0.8(4) . . . . ? N3 C8 C9 C10 173.7(2) . . . . ? C13 C8 C9 C15 180.0(2) . . . . ? N3 C8 C9 C15 -5.6(4) . . . . ? C8 C9 C10 C11 -0.8(4) . . . . ? C15 C9 C10 C11 178.5(3) . . . . ? C9 C10 C11 C12 1.1(4) . . . . ? C10 C11 C12 C13 0.2(5) . . . . ? C11 C12 C13 C8 -1.7(4) . . . . ? C11 C12 C13 C14 174.6(3) . . . . ? C9 C8 C13 C12 2.0(4) . . . . ? N3 C8 C13 C12 -172.5(2) . . . . ? C9 C8 C13 C14 -174.2(3) . . . . ? N3 C8 C13 C14 11.3(4) . . . . ? C21 C16 C17 C18 -0.6(4) . . . . ? N1 C16 C17 C18 -177.5(3) . . . . ? C21 C16 C17 C23 179.7(3) . . . . ? N1 C16 C17 C23 2.7(4) . . . . ? C16 C17 C18 C19 -0.6(5) . . . . ? C23 C17 C18 C19 179.2(3) . . . . ? C17 C18 C19 C20 1.6(6) . . . . ? C18 C19 C20 C21 -1.5(6) . . . . ? C19 C20 C21 C16 0.3(5) . . . . ? C19 C20 C21 C22 -178.8(3) . . . . ? C17 C16 C21 C20 0.7(4) . . . . ? N1 C16 C21 C20 177.7(3) . . . . ? C17 C16 C21 C22 179.8(3) . . . . ? N1 C16 C21 C22 -3.2(4) . . . . ? N5 C24 C25 N4 -59.9(3) . . . . ? O1 C1 N1 C16 -0.5(4) . . . . ? C2 C1 N1 C16 -177.4(2) . . . . ? O1 C1 N1 Cu1 -177.9(2) . . . . ? C2 C1 N1 Cu1 5.1(3) . . . . ? C17 C16 N1 C1 -66.4(4) . . . . ? C21 C16 N1 C1 116.6(3) . . . . ? C17 C16 N1 Cu1 110.8(3) . . . . ? C21 C16 N1 Cu1 -66.2(3) . . . . ? C3 C2 N2 C6 -4.9(4) . . . . ? C1 C2 N2 C6 171.7(2) . . . . ? C3 C2 N2 Cu1 168.2(2) . . . . ? C1 C2 N2 Cu1 -15.2(3) . . . . ? C5 C6 N2 C2 2.6(4) . . . . ? C7 C6 N2 C2 -179.9(2) . . . . ? C5 C6 N2 Cu1 -170.5(2) . . . . ? C7 C6 N2 Cu1 7.1(3) . . . . ? O2 C7 N3 C8 5.8(4) . . . . ? C6 C7 N3 C8 -173.8(2) . . . . ? O2 C7 N3 Cu1 179.4(2) . . . . ? C6 C7 N3 Cu1 -0.2(3) . . . . ? C13 C8 N3 C7 -121.9(3) . . . . ? C9 C8 N3 C7 63.6(3) . . . . ? C13 C8 N3 Cu1 65.0(3) . . . . ? C9 C8 N3 Cu1 -109.5(3) . . . . ? C24 C25 N4 Cu1 46.1(3) . . . . ? C25 C24 N5 Cu1 41.0(2) . . . . ?