#------------------------------------------------------------------------------ #$Date: 2018-01-16 04:34:49 +0200 (Tue, 16 Jan 2018) $ #$Revision: 205237 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229971.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_7229971 loop_ _publ_author_name 'Dankhoff, Katja' 'Weber, Birgit' _publ_section_title ; Novel Cu(II) complexes with NNO-Schiff base-like ligands -- structures and magnetic properties ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C7CE02007D _journal_year 2018 _chemical_formula_moiety 'C12 H14 Cu N3 O3, N O3, H2 O' _chemical_formula_sum 'C12 H16 Cu N4 O7' _chemical_formula_weight 391.83 _chemical_name_common '[CuL30dNO3]' _chemical_name_systematic ; ? ; _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2017-07-27 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-01-11 deposited with the CCDC. 2018-01-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.232(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.0597(6) _cell_length_b 14.5372(7) _cell_length_c 11.8354(8) _cell_measurement_reflns_used 8319 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 28.52 _cell_measurement_theta_min 2.23 _cell_volume 1552.26(17) _computing_cell_refinement X-AREA-STOE _computing_data_collection X-AREA-STOE _computing_data_reduction X-AREA-STOE _computing_molecular_graphics ORTEP-III _computing_publication_material PLATON _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution SIR97 _diffrn_ambient_temperature 133(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.937 _diffrn_measurement_device_type STOE-STADIVARI _diffrn_measurement_method omega-scan _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_unetI/netI 0.0421 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.937 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 11415 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.937 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.533 _diffrn_reflns_theta_min 2.225 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 1.452 _exptl_absorpt_correction_type none _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 804 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.109 _exptl_crystal_size_min 0.083 _refine_diff_density_max 0.394 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 233 _refine_ls_number_reflns 3688 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.906 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0274 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0305P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.0605 _reflns_number_gt 2876 _reflns_number_total 3688 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce02007d2.cif _cod_data_source_block cl118 _cod_database_code 7229971 _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_res_file ; shelx.res created by SHELXL-2014/7 TITL SIR97 run in space group P 21/c CELL 0.71073 9.0597 14.5372 11.8354 90.000 95.232 90.000 ZERR 4.00 0.0006 0.0007 0.0008 0.000 0.005 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O CU UNIT 48 64 16 28 4 MERG 2 FMAP 2 PLAN 10 ACTA BOND $H CONF LIST 4 L.S. 20 TEMP -140.00 WGHT 0.030500 FVAR 0.24614 C1 1 0.222345 -0.118269 0.505652 11.00000 0.02574 0.01509 = 0.02293 -0.00148 0.00379 -0.00037 AFIX 43 H1 2 0.175879 -0.164821 0.546215 11.00000 -1.20000 AFIX 0 C2 1 0.306375 -0.143707 0.419281 11.00000 0.03080 0.01727 = 0.02827 -0.00499 0.00639 0.00247 AFIX 43 H2 2 0.316891 -0.206722 0.400318 11.00000 -1.20000 AFIX 0 C3 1 0.375087 -0.076080 0.360709 11.00000 0.03598 0.02678 = 0.02349 -0.00188 0.01153 0.00444 AFIX 43 H3 2 0.435340 -0.092056 0.302079 11.00000 -1.20000 AFIX 0 C4 1 0.354858 0.014956 0.388665 11.00000 0.03771 0.02167 = 0.02540 0.00336 0.01308 -0.00090 AFIX 43 H4 2 0.399629 0.062472 0.348525 11.00000 -1.20000 AFIX 0 C5 1 0.268312 0.036384 0.476147 11.00000 0.02342 0.01524 = 0.01730 0.00122 0.00203 0.00076 C6 1 0.245841 0.133765 0.513192 11.00000 0.02772 0.01402 = 0.02125 0.00140 0.00838 -0.00039 AFIX 23 H6A 2 0.342686 0.161580 0.539437 11.00000 -1.20000 H6B 2 0.201150 0.170358 0.448298 11.00000 -1.20000 AFIX 0 C7 1 0.106924 0.214950 0.639790 11.00000 0.01996 0.01117 = 0.01917 0.00189 -0.00128 -0.00116 AFIX 43 H7 2 0.133608 0.267703 0.598867 11.00000 -1.20000 AFIX 0 C8 1 0.024269 0.228890 0.734568 11.00000 0.02087 0.00864 = 0.02259 -0.00114 0.00198 0.00063 C9 1 -0.015711 0.156472 0.806840 11.00000 0.01920 0.01211 = 0.02085 -0.00154 0.00102 0.00025 C10 1 -0.126291 0.114273 0.975715 11.00000 0.04266 0.01579 = 0.01824 0.00160 0.00762 0.00206 AFIX 23 H10A 2 -0.150085 0.144769 1.046613 11.00000 -1.20000 H10B 2 -0.040724 0.072968 0.994665 11.00000 -1.20000 AFIX 0 C11 1 -0.256577 0.058092 0.929804 11.00000 0.05044 0.03805 = 0.03058 -0.00225 0.01781 -0.01584 AFIX 133 H11A 2 -0.340969 0.098769 0.909032 11.00000 -1.50000 H11B 2 -0.282810 0.014387 0.987761 11.00000 -1.50000 H11C 2 -0.231290 0.024321 0.862547 11.00000 -1.50000 AFIX 0 C12 1 0.010863 -0.179692 0.736785 11.00000 0.01964 0.01435 = 0.01829 -0.00156 0.00254 0.00091 N1 3 0.203995 -0.029616 0.534381 11.00000 0.02136 0.01118 = 0.01942 -0.00027 0.00277 -0.00044 N2 3 0.148489 0.135453 0.605204 11.00000 0.01967 0.01159 = 0.01946 0.00033 0.00312 0.00000 N3 3 0.037395 -0.105518 0.713282 11.00000 0.02701 0.01218 = 0.02341 -0.00114 0.00792 -0.00039 N21 3 0.507696 0.302914 0.722447 11.00000 0.02626 0.01743 = 0.02705 -0.00701 0.00155 -0.00079 O1 4 0.009610 0.073170 0.792962 11.00000 0.02706 0.00912 = 0.02343 0.00019 0.00683 0.00044 O2 4 -0.084843 0.184281 0.895533 11.00000 0.03090 0.01191 = 0.02289 0.00083 0.00883 0.00368 O21 4 0.604697 0.293943 0.798818 11.00000 0.05198 0.08990 = 0.04317 0.02016 -0.02369 -0.02286 O22 4 0.530635 0.349583 0.635632 11.00000 0.04794 0.02586 = 0.02758 -0.00021 0.00131 -0.00896 O23 4 0.388828 0.265072 0.729139 11.00000 0.03523 0.08196 = 0.06563 0.02787 -0.01035 -0.02986 O31 4 0.326502 0.010373 0.778076 11.00000 0.02865 0.01768 = 0.02327 -0.00191 -0.00158 0.00392 O32 4 0.342481 0.156122 0.926173 11.00000 0.04750 0.02098 = 0.02779 -0.00286 -0.00214 -0.00119 CU1 5 0.113904 0.016432 0.671399 11.00000 0.02077 0.00733 = 0.01855 -0.00014 0.00468 -0.00019 H31A 2 0.336115 0.043471 0.827823 11.00000 0.04089 H31B 2 0.357943 -0.031862 0.806760 11.00000 0.04880 H32A 2 0.391242 0.160345 0.984586 11.00000 0.05426 H32B 2 0.375879 0.189931 0.882763 11.00000 0.05386 HKLF 4 REM SIR97 run in space group P 21/c REM R1 = 0.0274 for 2876 Fo > 4sig(Fo) and 0.0410 for all 3688 data REM 233 parameters refined using 0 restraints END WGHT 0.0305 0.0000 REM Highest difference peak 0.394, deepest hole -0.286, 1-sigma level 0.062 Q1 1 0.5418 0.3198 0.8248 11.00000 0.05 0.39 Q2 1 0.5749 0.2531 0.7849 11.00000 0.05 0.37 Q3 1 0.0551 0.2153 0.6863 11.00000 0.05 0.29 Q4 1 0.2617 -0.1260 0.4560 11.00000 0.05 0.27 Q5 1 0.6336 0.3108 0.7653 11.00000 0.05 0.27 Q6 1 -0.0142 0.1899 0.7598 11.00000 0.05 0.26 Q7 1 0.1434 -0.0120 0.5704 11.00000 0.05 0.25 Q8 1 -0.0994 0.1484 0.9416 11.00000 0.05 0.25 Q9 1 0.0288 0.2683 0.7523 11.00000 0.05 0.24 Q10 1 0.2944 0.0201 0.4198 11.00000 0.05 0.24 ; _shelx_res_checksum 40984 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 C1 C 0.2223(2) -0.11827(13) 0.50565(16) 0.0212(4) Uani 1 1 d . . H1 H 0.1759 -0.1648 0.5462 0.025 Uiso 1 1 calc R U C2 C 0.3064(2) -0.14371(14) 0.41928(18) 0.0252(4) Uani 1 1 d . . H2 H 0.3169 -0.2067 0.4003 0.030 Uiso 1 1 calc R U C3 C 0.3751(2) -0.07608(15) 0.36071(18) 0.0282(4) Uani 1 1 d . . H3 H 0.4353 -0.0921 0.3021 0.034 Uiso 1 1 calc R U C4 C 0.3549(2) 0.01496(15) 0.38867(17) 0.0276(4) Uani 1 1 d . . H4 H 0.3996 0.0625 0.3485 0.033 Uiso 1 1 calc R U C5 C 0.26831(19) 0.03638(12) 0.47615(15) 0.0186(4) Uani 1 1 d . . C6 C 0.2458(2) 0.13376(12) 0.51319(17) 0.0206(4) Uani 1 1 d . . H6A H 0.3427 0.1616 0.5394 0.025 Uiso 1 1 calc R U H6B H 0.2011 0.1704 0.4483 0.025 Uiso 1 1 calc R U C7 C 0.10692(18) 0.21495(12) 0.63979(15) 0.0170(3) Uani 1 1 d . . H7 H 0.1336 0.2677 0.5989 0.020 Uiso 1 1 calc R U C8 C 0.02427(18) 0.22889(12) 0.73457(16) 0.0174(4) Uani 1 1 d . . C9 C -0.01571(18) 0.15647(12) 0.80684(16) 0.0174(4) Uani 1 1 d . . C10 C -0.1263(2) 0.11427(13) 0.97572(17) 0.0253(4) Uani 1 1 d . . H10A H -0.1501 0.1448 1.0466 0.030 Uiso 1 1 calc R U H10B H -0.0407 0.0730 0.9947 0.030 Uiso 1 1 calc R U C11 C -0.2566(3) 0.05809(17) 0.9298(2) 0.0388(6) Uani 1 1 d . . H11A H -0.3410 0.0988 0.9090 0.058 Uiso 1 1 calc R U H11B H -0.2828 0.0144 0.9878 0.058 Uiso 1 1 calc R U H11C H -0.2313 0.0243 0.8625 0.058 Uiso 1 1 calc R U C12 C 0.01086(19) -0.17969(12) 0.73679(15) 0.0174(4) Uani 1 1 d . . N1 N 0.20400(15) -0.02962(10) 0.53438(13) 0.0173(3) Uani 1 1 d . . N2 N 0.14849(15) 0.13545(10) 0.60520(13) 0.0168(3) Uani 1 1 d . . N3 N 0.03740(16) -0.10552(10) 0.71328(14) 0.0205(3) Uani 1 1 d . . N21 N 0.50770(17) 0.30291(11) 0.72245(15) 0.0236(3) Uani 1 1 d . . O1 O 0.00961(13) 0.07317(8) 0.79296(11) 0.0196(3) Uani 1 1 d . . O2 O -0.08484(14) 0.18428(8) 0.89553(11) 0.0215(3) Uani 1 1 d . . O21 O 0.6047(2) 0.29394(17) 0.79882(17) 0.0634(6) Uani 1 1 d . . O22 O 0.53063(18) 0.34958(10) 0.63563(13) 0.0339(3) Uani 1 1 d . . O23 O 0.38883(19) 0.26507(16) 0.72914(18) 0.0619(6) Uani 1 1 d . . O31 O 0.32650(15) 0.01037(12) 0.77808(13) 0.0234(3) Uani 1 1 d . . O32 O 0.3425(2) 0.15612(11) 0.92617(17) 0.0324(3) Uani 1 1 d . . Cu1 Cu 0.11390(2) 0.01643(2) 0.67140(2) 0.01537(6) Uani 1 1 d . . H31A H 0.336(3) 0.043(2) 0.828(3) 0.041(8) Uiso 1 1 d . . H31B H 0.358(3) -0.032(2) 0.807(3) 0.049(9) Uiso 1 1 d . . H32A H 0.391(3) 0.160(2) 0.985(3) 0.054(9) Uiso 1 1 d . . H32B H 0.376(3) 0.190(2) 0.883(3) 0.054(9) Uiso 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 C1 0.0257(9) 0.0151(9) 0.0229(10) -0.0015(7) 0.0038(7) -0.0004(7) C2 0.0308(10) 0.0173(9) 0.0283(11) -0.0050(8) 0.0064(8) 0.0025(7) C3 0.0360(11) 0.0268(11) 0.0235(10) -0.0019(8) 0.0115(8) 0.0044(8) C4 0.0377(10) 0.0217(9) 0.0254(10) 0.0034(9) 0.0131(8) -0.0009(8) C5 0.0234(9) 0.0152(9) 0.0173(9) 0.0012(7) 0.0020(7) 0.0008(6) C6 0.0277(10) 0.0140(9) 0.0213(10) 0.0014(7) 0.0084(7) -0.0004(6) C7 0.0200(8) 0.0112(8) 0.0192(9) 0.0019(6) -0.0013(7) -0.0012(6) C8 0.0209(9) 0.0086(8) 0.0226(10) -0.0011(7) 0.0020(7) 0.0006(6) C9 0.0192(8) 0.0121(8) 0.0209(9) -0.0015(7) 0.0010(7) 0.0003(6) C10 0.0427(11) 0.0158(9) 0.0182(10) 0.0016(7) 0.0076(8) 0.0021(7) C11 0.0504(14) 0.0380(13) 0.0306(13) -0.0022(10) 0.0178(10) -0.0158(10) C12 0.0196(9) 0.0143(9) 0.0183(9) -0.0016(7) 0.0025(7) 0.0009(6) N1 0.0214(7) 0.0112(8) 0.0194(7) -0.0003(6) 0.0028(6) -0.0004(5) N2 0.0197(7) 0.0116(7) 0.0195(8) 0.0003(6) 0.0031(6) 0.0000(5) N3 0.0270(8) 0.0122(8) 0.0234(8) -0.0011(6) 0.0079(6) -0.0004(6) N21 0.0263(8) 0.0174(8) 0.0271(9) -0.0070(7) 0.0016(7) -0.0008(6) O1 0.0271(7) 0.0091(6) 0.0234(7) 0.0002(5) 0.0068(5) 0.0004(4) O2 0.0309(7) 0.0119(6) 0.0229(7) 0.0008(5) 0.0088(5) 0.0037(5) O21 0.0520(11) 0.0899(16) 0.0432(11) 0.0202(11) -0.0237(9) -0.0229(10) O22 0.0479(9) 0.0259(8) 0.0276(8) -0.0002(6) 0.0013(7) -0.0090(6) O23 0.0352(10) 0.0820(15) 0.0656(14) 0.0279(11) -0.0103(9) -0.0299(9) O31 0.0286(7) 0.0177(7) 0.0233(8) -0.0019(6) -0.0016(5) 0.0039(6) O32 0.0475(10) 0.0210(8) 0.0278(9) -0.0029(7) -0.0021(8) -0.0012(6) Cu1 0.02077(11) 0.00733(9) 0.01855(11) -0.00014(9) 0.00468(7) -0.00019(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' O O 0.0106 0.0060 '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_ _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 N1 C1 C2 122.18(18) . . N1 C1 H1 118.9 . . C2 C1 H1 118.9 . . C1 C2 C3 119.00(18) . . C1 C2 H2 120.5 . . C3 C2 H2 120.5 . . C4 C3 C2 119.05(18) . . C4 C3 H3 120.5 . . C2 C3 H3 120.5 . . C3 C4 C5 119.32(18) . . C3 C4 H4 120.3 . . C5 C4 H4 120.3 . . N1 C5 C4 121.48(17) . . N1 C5 C6 116.52(15) . . C4 C5 C6 121.98(16) . . N2 C6 C5 109.89(14) . . N2 C6 H6A 109.7 . . C5 C6 H6A 109.7 . . N2 C6 H6B 109.7 . . C5 C6 H6B 109.7 . . H6A C6 H6B 108.2 . . N2 C7 C8 124.59(16) . . N2 C7 H7 117.7 . . C8 C7 H7 117.7 . . C12 C8 C7 118.04(15) 2_556 . C12 C8 C9 118.38(15) 2_556 . C7 C8 C9 123.42(15) . . O1 C9 O2 120.25(16) . . O1 C9 C8 125.40(16) . . O2 C9 C8 114.35(15) . . O2 C10 C11 112.62(17) . . O2 C10 H10A 109.1 . . C11 C10 H10A 109.1 . . O2 C10 H10B 109.1 . . C11 C10 H10B 109.1 . . H10A C10 H10B 107.8 . . C10 C11 H11A 109.5 . . C10 C11 H11B 109.5 . . H11A C11 H11B 109.5 . . C10 C11 H11C 109.5 . . H11A C11 H11C 109.5 . . H11B C11 H11C 109.5 . . N3 C12 C8 179.13(19) . 2_546 C5 N1 C1 118.95(16) . . C5 N1 Cu1 113.92(12) . . C1 N1 Cu1 126.50(12) . . C7 N2 C6 117.60(15) . . C7 N2 Cu1 127.42(13) . . C6 N2 Cu1 114.64(11) . . C12 N3 Cu1 171.49(14) . . O21 N21 O23 119.3(2) . . O21 N21 O22 120.23(18) . . O23 N21 O22 120.46(18) . . C9 O1 Cu1 127.49(12) . . C9 O2 C10 117.80(14) . . Cu1 O31 H31A 117(2) . . Cu1 O31 H31B 125(2) . . H31A O31 H31B 99(3) . . H32A O32 H32B 108(3) . . N2 Cu1 O1 91.57(6) . . N2 Cu1 N3 166.67(7) . . O1 Cu1 N3 89.42(6) . . N2 Cu1 N1 82.98(6) . . O1 Cu1 N1 172.39(6) . . N3 Cu1 N1 94.67(6) . . N2 Cu1 O31 95.86(6) . . O1 Cu1 O31 92.90(6) . . N3 Cu1 O31 97.36(6) . . N1 Cu1 O31 92.94(6) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 N1 1.347(2) . C1 C2 1.380(3) . C1 H1 0.9500 . C2 C3 1.383(3) . C2 H2 0.9500 . C3 C4 1.380(3) . C3 H3 0.9500 . C4 C5 1.390(2) . C4 H4 0.9500 . C5 N1 1.345(2) . C5 C6 1.501(2) . C6 N2 1.463(2) . C6 H6A 0.9900 . C6 H6B 0.9900 . C7 N2 1.293(2) . C7 C8 1.419(2) . C7 H7 0.9500 . C8 C12 1.415(2) 2_556 C8 C9 1.424(2) . C9 O1 1.246(2) . C9 O2 1.333(2) . C10 O2 1.464(2) . C10 C11 1.496(3) . C10 H10A 0.9900 . C10 H10B 0.9900 . C11 H11A 0.9800 . C11 H11B 0.9800 . C11 H11C 0.9800 . C12 N3 1.145(2) . C12 C8 1.415(2) 2_546 N1 Cu1 1.9964(15) . N2 Cu1 1.9366(14) . N3 Cu1 1.9828(15) . N21 O21 1.209(2) . N21 O23 1.218(2) . N21 O22 1.264(2) . O1 Cu1 1.9726(13) . O31 Cu1 2.2064(14) . O31 H31A 0.76(3) . O31 H31B 0.75(3) . O32 H32A 0.79(3) . O32 H32B 0.79(3) . 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_4 N1 C1 C2 C3 0.5(3) . . C1 C2 C3 C4 -1.4(3) . . C2 C3 C4 C5 1.1(3) . . C3 C4 C5 N1 0.1(3) . . C3 C4 C5 C6 178.04(19) . . N1 C5 C6 N2 -2.8(2) . . C4 C5 C6 N2 179.16(17) . . N2 C7 C8 C12 178.93(17) . 2_556 N2 C7 C8 C9 3.6(3) . . C12 C8 C9 O1 -179.13(17) 2_556 . C7 C8 C9 O1 -3.8(3) . . C12 C8 C9 O2 0.5(2) 2_556 . C7 C8 C9 O2 175.79(16) . . C4 C5 N1 C1 -1.1(3) . . C6 C5 N1 C1 -179.10(16) . . C4 C5 N1 Cu1 170.42(15) . . C6 C5 N1 Cu1 -7.6(2) . . C2 C1 N1 C5 0.8(3) . . C2 C1 N1 Cu1 -169.56(14) . . C8 C7 N2 C6 -173.93(16) . . C8 C7 N2 Cu1 -0.9(3) . . C5 C6 N2 C7 -173.77(16) . . C5 C6 N2 Cu1 12.34(19) . . O2 C9 O1 Cu1 -178.30(11) . . C8 C9 O1 Cu1 1.3(3) . . O1 C9 O2 C10 1.2(2) . . C8 C9 O2 C10 -178.43(15) . . C11 C10 O2 C9 -74.4(2) . .