#------------------------------------------------------------------------------ #$Date: 2019-11-17 09:06:29 +0200 (Sun, 17 Nov 2019) $ #$Revision: 229011 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229981.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_7229981 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_issue 6 _journal_name_full CrystEngComm _journal_page_first 818 _journal_paper_doi 10.1039/C7CE02007D _journal_volume 20 _journal_year 2018 _chemical_formula_moiety 'C26 H30 Cu2 N6 O12' _chemical_formula_sum 'C26 H30 Cu2 N6 O12' _chemical_formula_weight 745.64 _chemical_name_common '[CuL30aNO3]' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _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 105.798(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.7796(5) _cell_length_b 13.8977(8) _cell_length_c 16.9969(6) _cell_measurement_reflns_used 10957 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 26.62 _cell_measurement_theta_min 2.22 _cell_volume 2904.7(2) _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 0.979 _diffrn_measured_fraction_theta_max 0.933 _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 0.0237 _diffrn_reflns_av_unetI/netI 0.0250 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.933 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 9232 _diffrn_reflns_point_group_measured_fraction_full 0.979 _diffrn_reflns_point_group_measured_fraction_max 0.933 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.459 _diffrn_reflns_theta_min 2.211 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 1.540 _exptl_absorpt_correction_type none _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1528 _exptl_crystal_size_max 0.118 _exptl_crystal_size_mid 0.093 _exptl_crystal_size_min 0.088 _refine_diff_density_max 0.830 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.091 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 3429 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0251 _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^)+(0.0481P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0670 _refine_ls_wR_factor_ref 0.0766 _reflns_number_gt 2893 _reflns_number_total 3429 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce02007d2.cif _cod_data_source_block cl117 _cod_depositor_comments 'Adding full bibliography for 7229962--7229987.cif.' _cod_database_code 7229981 _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 C 2/c CELL 0.71073 12.7796 13.8977 16.9969 90.000 105.798 90.000 ZERR 4.00 0.0005 0.0008 0.0006 0.000 0.003 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H N O CU UNIT 104 120 24 48 8 MERG 2 FMAP 2 PLAN 10 ACTA BOND $H CONF LIST 4 L.S. 20 TEMP -140.00 WGHT 0.048100 FVAR 0.11862 C1 1 -0.230946 0.115957 0.125953 11.00000 0.01538 0.02782 = 0.01537 0.00068 0.00481 0.00093 AFIX 43 H1 2 -0.209601 0.112880 0.183980 11.00000 -1.20000 AFIX 0 C2 1 -0.340354 0.119825 0.085516 11.00000 0.01563 0.02997 = 0.02080 0.00142 0.00706 0.00118 AFIX 43 H2 2 -0.393509 0.119124 0.115191 11.00000 -1.20000 AFIX 0 C3 1 -0.371341 0.124764 0.000619 11.00000 0.01447 0.02898 = 0.02083 -0.00109 0.00065 0.00153 AFIX 43 H3 2 -0.446105 0.126941 -0.028651 11.00000 -1.20000 AFIX 0 C4 1 -0.292214 0.126456 -0.040454 11.00000 0.01539 0.02472 = 0.01559 -0.00021 0.00153 0.00227 AFIX 43 H4 2 -0.311675 0.130275 -0.098438 11.00000 -1.20000 AFIX 0 C5 1 -0.183693 0.122517 0.003861 11.00000 0.01506 0.01554 = 0.01395 -0.00034 0.00356 0.00064 C6 1 -0.093472 0.125008 -0.037203 11.00000 0.01234 0.02431 = 0.01160 0.00147 0.00225 0.00139 AFIX 23 H6A 2 -0.099269 0.068610 -0.073723 11.00000 -1.20000 H6B 2 -0.099636 0.183955 -0.070862 11.00000 -1.20000 AFIX 0 C7 1 0.098461 0.129163 -0.001142 11.00000 0.01462 0.01621 = 0.01306 -0.00012 0.00498 -0.00061 AFIX 43 H7 2 0.087677 0.136994 -0.058323 11.00000 -1.20000 AFIX 0 C8 1 0.208143 0.124529 0.047995 11.00000 0.01447 0.01859 = 0.01492 -0.00045 0.00602 -0.00052 C9 1 0.234341 0.112928 0.133217 11.00000 0.01328 0.02350 = 0.01675 0.00084 0.00396 0.00043 C10 1 0.350083 0.102276 0.184982 11.00000 0.01579 0.05227 = 0.01727 0.00457 0.00431 0.00414 AFIX 133 H10A 2 0.350357 0.087009 0.241328 11.00000 -1.50000 H10B 2 0.389430 0.162636 0.184195 11.00000 -1.50000 H10C 2 0.385658 0.050261 0.163055 11.00000 -1.50000 AFIX 0 C11 1 0.293885 0.130151 0.004776 11.00000 0.01450 0.01976 = 0.01771 -0.00069 0.00723 -0.00050 C12 1 0.324744 0.135627 -0.127139 11.00000 0.01776 0.03067 = 0.01798 -0.00266 0.01056 -0.00495 AFIX 23 H12A 2 0.378341 0.082544 -0.118426 11.00000 -1.20000 H12B 2 0.364383 0.197294 -0.113753 11.00000 -1.20000 AFIX 0 C13 1 0.254761 0.136122 -0.214402 11.00000 0.02285 0.05183 = 0.01935 -0.00258 0.00783 -0.00600 AFIX 133 H13A 2 0.220710 0.072877 -0.227955 11.00000 -1.50000 H13B 2 0.299950 0.150446 -0.251178 11.00000 -1.50000 H13C 2 0.198178 0.185363 -0.220741 11.00000 -1.50000 AFIX 0 N1 3 -0.153414 0.116409 0.085673 11.00000 0.01276 0.01870 = 0.01231 0.00025 0.00246 0.00019 N2 3 0.011735 0.123741 0.024497 11.00000 0.01464 0.01856 = 0.01249 0.00091 0.00338 0.00080 N11 3 0.000000 -0.027282 0.250000 10.50000 0.01221 0.02859 = 0.01411 0.00000 0.00280 0.00000 N21 3 0.000000 0.310557 0.250000 10.50000 0.01411 0.02817 = 0.02162 0.00000 0.00486 0.00000 O1 4 0.162646 0.108828 0.173156 11.00000 0.01309 0.03525 = 0.01239 0.00313 0.00375 0.00112 O2 4 0.390334 0.141305 0.034930 11.00000 0.01386 0.04137 = 0.02079 0.00162 0.00519 -0.00173 O3 4 0.250702 0.122139 -0.076724 11.00000 0.01427 0.03498 = 0.01573 -0.00401 0.00823 -0.00506 O11 4 0.000000 0.068501 0.250000 10.50000 0.01930 0.01991 = 0.01540 0.00000 0.00446 0.00000 O12 4 0.001127 -0.066382 0.186288 11.00000 0.02670 0.03344 = 0.01473 -0.00634 0.00603 -0.00018 O21 4 -0.023438 0.266857 0.183442 11.00000 0.03053 0.03181 = 0.01755 -0.00152 0.00166 0.00333 O22 4 0.000000 0.399638 0.250000 10.50000 0.04058 0.01842 = 0.03886 0.00000 0.01174 0.00000 CU1 5 0.006496 0.115316 0.135699 11.00000 0.01031 0.02376 = 0.00985 0.00188 0.00281 0.00025 HKLF 4 REM SIR97 run in space group C 2/c REM R1 = 0.0251 for 2893 Fo > 4sig(Fo) and 0.0335 for all 3429 data REM 210 parameters refined using 0 restraints END WGHT 0.0481 0.0000 REM Highest difference peak 0.830, deepest hole -0.402, 1-sigma level 0.091 Q1 1 0.0000 0.1665 0.2500 10.50000 0.05 0.83 Q2 1 0.0000 0.2481 0.2500 10.50000 0.05 0.67 Q3 1 -0.1591 0.1178 -0.0087 11.00000 0.05 0.47 Q4 1 -0.2828 0.1175 0.1089 11.00000 0.05 0.46 Q5 1 0.2399 0.1332 0.0282 11.00000 0.05 0.45 Q6 1 0.1025 0.1175 0.1408 11.00000 0.05 0.44 Q7 1 0.2949 0.1113 0.1607 11.00000 0.05 0.42 Q8 1 -0.1013 0.1195 0.1112 11.00000 0.05 0.42 Q9 1 -0.0381 0.1255 -0.0098 11.00000 0.05 0.42 Q10 1 0.1593 0.1240 0.0217 11.00000 0.05 0.41 ; _shelx_res_checksum 15363 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy C1 C -0.23095(14) 0.11596(13) 0.12595(11) 0.0194(3) Uani 1 1 d . . . H1 H -0.2096 0.1129 0.1840 0.023 Uiso 1 1 calc R U . C2 C -0.34035(15) 0.11983(14) 0.08552(11) 0.0217(4) Uani 1 1 d . . . H2 H -0.3935 0.1191 0.1152 0.026 Uiso 1 1 calc R U . C3 C -0.37134(15) 0.12476(14) 0.00062(11) 0.0222(4) Uani 1 1 d . . . H3 H -0.4461 0.1269 -0.0287 0.027 Uiso 1 1 calc R U . C4 C -0.29221(14) 0.12646(13) -0.04045(11) 0.0191(3) Uani 1 1 d . . . H4 H -0.3117 0.1303 -0.0984 0.023 Uiso 1 1 calc R U . C5 C -0.18369(14) 0.12252(12) 0.00386(10) 0.0149(3) Uani 1 1 d . . . C6 C -0.09347(14) 0.12501(12) -0.03720(10) 0.0163(3) Uani 1 1 d . . . H6A H -0.0993 0.0686 -0.0737 0.020 Uiso 1 1 calc R U . H6B H -0.0996 0.1840 -0.0709 0.020 Uiso 1 1 calc R U . C7 C 0.09846(14) 0.12916(11) -0.00114(10) 0.0144(3) Uani 1 1 d . . . H7 H 0.0877 0.1370 -0.0583 0.017 Uiso 1 1 calc R U . C8 C 0.20814(14) 0.12453(12) 0.04799(10) 0.0156(3) Uani 1 1 d . . . C9 C 0.23434(14) 0.11293(12) 0.13322(11) 0.0179(3) Uani 1 1 d . . . C10 C 0.35008(16) 0.10228(17) 0.18498(12) 0.0285(4) Uani 1 1 d . . . H10A H 0.3504 0.0870 0.2413 0.043 Uiso 1 1 calc R U . H10B H 0.3894 0.1626 0.1842 0.043 Uiso 1 1 calc R U . H10C H 0.3857 0.0503 0.1631 0.043 Uiso 1 1 calc R U . C11 C 0.29389(14) 0.13015(12) 0.00478(10) 0.0168(3) Uani 1 1 d . . . C12 C 0.32474(15) 0.13563(14) -0.12714(11) 0.0210(4) Uani 1 1 d . . . H12A H 0.3783 0.0825 -0.1184 0.025 Uiso 1 1 calc R U . H12B H 0.3644 0.1973 -0.1138 0.025 Uiso 1 1 calc R U . C13 C 0.25476(18) 0.13612(18) -0.21440(12) 0.0309(5) Uani 1 1 d . . . H13A H 0.2207 0.0729 -0.2280 0.046 Uiso 1 1 calc R U . H13B H 0.3000 0.1504 -0.2512 0.046 Uiso 1 1 calc R U . H13C H 0.1982 0.1854 -0.2207 0.046 Uiso 1 1 calc R U . N1 N -0.15341(12) 0.11641(10) 0.08567(8) 0.0148(3) Uani 1 1 d . . . N2 N 0.01174(12) 0.12374(10) 0.02450(8) 0.0153(3) Uani 1 1 d . . . N11 N 0.0000 -0.02728(16) 0.2500 0.0185(4) Uani 1 2 d S T P N21 N 0.0000 0.31056(16) 0.2500 0.0213(4) Uani 1 2 d S T P O1 O 0.16265(10) 0.10883(9) 0.17316(7) 0.0202(3) Uani 1 1 d . . . O2 O 0.39033(11) 0.14130(11) 0.03493(8) 0.0253(3) Uani 1 1 d . . . O3 O 0.25070(10) 0.12214(10) -0.07672(8) 0.0208(3) Uani 1 1 d . . . O11 O 0.0000 0.06850(12) 0.2500 0.0183(3) Uani 1 2 d S T P O12 O 0.00113(11) -0.06638(10) 0.18629(7) 0.0249(3) Uani 1 1 d . . . O21 O -0.02344(12) 0.26686(10) 0.18344(8) 0.0276(3) Uani 1 1 d . . . O22 O 0.0000 0.39964(14) 0.2500 0.0324(5) Uani 1 2 d S T P Cu1 Cu 0.00650(2) 0.11532(2) 0.13570(2) 0.01463(8) 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 C1 0.0154(8) 0.0278(9) 0.0154(8) 0.0007(6) 0.0048(6) 0.0009(7) C2 0.0156(9) 0.0300(9) 0.0208(9) 0.0014(6) 0.0071(7) 0.0012(7) C3 0.0145(8) 0.0290(10) 0.0208(9) -0.0011(7) 0.0006(6) 0.0015(7) C4 0.0154(8) 0.0247(9) 0.0156(8) -0.0002(6) 0.0015(6) 0.0023(6) C5 0.0151(8) 0.0155(7) 0.0139(7) -0.0003(5) 0.0036(6) 0.0006(6) C6 0.0123(8) 0.0243(8) 0.0116(7) 0.0015(6) 0.0022(6) 0.0014(6) C7 0.0146(8) 0.0162(8) 0.0131(7) -0.0001(5) 0.0050(6) -0.0006(6) C8 0.0145(8) 0.0186(8) 0.0149(8) -0.0005(5) 0.0060(6) -0.0005(6) C9 0.0133(8) 0.0235(8) 0.0167(8) 0.0008(6) 0.0040(6) 0.0004(6) C10 0.0158(9) 0.0523(13) 0.0173(9) 0.0046(8) 0.0043(7) 0.0041(8) C11 0.0145(8) 0.0198(8) 0.0177(8) -0.0007(6) 0.0072(6) -0.0005(6) C12 0.0178(8) 0.0307(10) 0.0180(8) -0.0027(6) 0.0106(7) -0.0049(7) C13 0.0228(10) 0.0518(13) 0.0194(9) -0.0026(8) 0.0078(8) -0.0060(9) N1 0.0128(7) 0.0187(7) 0.0123(6) 0.0003(5) 0.0025(5) 0.0002(5) N2 0.0146(7) 0.0186(7) 0.0125(6) 0.0009(5) 0.0034(5) 0.0008(5) N11 0.0122(9) 0.0286(11) 0.0141(9) 0.000 0.0028(7) 0.000 N21 0.0141(10) 0.0282(12) 0.0216(10) 0.000 0.0049(8) 0.000 O1 0.0131(6) 0.0353(7) 0.0124(6) 0.0031(5) 0.0037(5) 0.0011(5) O2 0.0139(6) 0.0414(8) 0.0208(6) 0.0016(5) 0.0052(5) -0.0017(5) O3 0.0143(6) 0.0350(7) 0.0157(6) -0.0040(5) 0.0082(5) -0.0051(5) O11 0.0193(9) 0.0199(9) 0.0154(8) 0.000 0.0045(6) 0.000 O12 0.0267(7) 0.0334(8) 0.0147(6) -0.0063(5) 0.0060(5) -0.0002(6) O21 0.0305(8) 0.0318(7) 0.0176(6) -0.0015(5) 0.0017(5) 0.0033(6) O22 0.0406(13) 0.0184(10) 0.0389(12) 0.000 0.0117(10) 0.000 Cu1 0.01031(12) 0.02376(12) 0.00985(11) 0.00188(7) 0.00281(7) 0.00025(7) 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 122.09(16) . . N1 C1 H1 119.0 . . C2 C1 H1 119.0 . . C1 C2 C3 118.83(17) . . C1 C2 H2 120.6 . . C3 C2 H2 120.6 . . C4 C3 C2 119.10(17) . . C4 C3 H3 120.5 . . C2 C3 H3 120.5 . . C3 C4 C5 119.19(16) . . C3 C4 H4 120.4 . . C5 C4 H4 120.4 . . N1 C5 C4 121.95(15) . . N1 C5 C6 116.24(15) . . C4 C5 C6 121.81(15) . . N2 C6 C5 109.79(13) . . 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 126.44(15) . . N2 C7 H7 116.8 . . C8 C7 H7 116.8 . . C9 C8 C7 122.02(15) . . C9 C8 C11 121.19(15) . . C7 C8 C11 116.78(14) . . O1 C9 C8 123.19(16) . . O1 C9 C10 114.56(15) . . C8 C9 C10 122.24(16) . . C9 C10 H10A 109.5 . . C9 C10 H10B 109.5 . . H10A C10 H10B 109.5 . . C9 C10 H10C 109.5 . . H10A C10 H10C 109.5 . . H10B C10 H10C 109.5 . . O2 C11 O3 122.05(15) . . O2 C11 C8 127.17(16) . . O3 C11 C8 110.77(14) . . O3 C12 C13 105.88(15) . . O3 C12 H12A 110.6 . . C13 C12 H12A 110.6 . . O3 C12 H12B 110.6 . . C13 C12 H12B 110.6 . . H12A C12 H12B 108.7 . . C12 C13 H13A 109.5 . . C12 C13 H13B 109.5 . . H13A C13 H13B 109.5 . . C12 C13 H13C 109.5 . . H13A C13 H13C 109.5 . . H13B C13 H13C 109.5 . . C5 N1 C1 118.83(15) . . C5 N1 Cu1 114.64(11) . . C1 N1 Cu1 126.46(12) . . C7 N2 C6 117.42(14) . . C7 N2 Cu1 126.70(12) . . C6 N2 Cu1 115.88(11) . . O12 N11 O12 126.9(2) . 2 O12 N11 O11 116.56(12) . . O12 N11 O11 116.56(12) 2 . O22 N21 O21 119.15(11) . 2 O22 N21 O21 119.16(11) . . O21 N21 O21 121.7(2) 2 . C9 O1 Cu1 130.48(12) . . C11 O3 C12 116.45(14) . . N11 O11 Cu1 108.30(5) . . N11 O11 Cu1 108.30(5) . 2 Cu1 O11 Cu1 143.39(9) . 2 N21 O21 Cu1 137.40(13) . . N2 Cu1 O1 91.01(6) . . N2 Cu1 N1 83.42(6) . . O1 Cu1 N1 173.86(5) . . N2 Cu1 O11 165.20(6) . . O1 Cu1 O11 88.72(4) . . N1 Cu1 O11 96.00(4) . . N2 Cu1 O21 110.04(5) . . O1 Cu1 O21 100.44(5) . . N1 Cu1 O21 83.96(5) . . O11 Cu1 O21 84.54(6) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 N1 1.349(2) . C1 C2 1.381(3) . C1 H1 0.9500 . C2 C3 1.390(3) . C2 H2 0.9500 . C3 C4 1.377(3) . C3 H3 0.9500 . C4 C5 1.387(2) . C4 H4 0.9500 . C5 N1 1.341(2) . C5 C6 1.502(2) . C6 N2 1.463(2) . C6 H6A 0.9900 . C6 H6B 0.9900 . C7 N2 1.299(2) . C7 C8 1.424(2) . C7 H7 0.9500 . C8 C9 1.404(2) . C8 C11 1.478(2) . C9 O1 1.281(2) . C9 C10 1.508(3) . C10 H10A 0.9800 . C10 H10B 0.9800 . C10 H10C 0.9800 . C11 O2 1.209(2) . C11 O3 1.349(2) . C12 O3 1.451(2) . C12 C13 1.509(3) . C12 H12A 0.9900 . C12 H12B 0.9900 . C13 H13A 0.9800 . C13 H13B 0.9800 . C13 H13C 0.9800 . N1 Cu1 1.9883(14) . N2 Cu1 1.9130(14) . N11 O12 1.2152(16) . N11 O12 1.2152(16) 2 N11 O11 1.331(3) . N21 O22 1.238(3) . N21 O21 1.2465(17) 2 N21 O21 1.2465(17) . O1 Cu1 1.9245(13) . O11 Cu1 2.0718(6) . O11 Cu1 2.0718(6) 2 O21 Cu1 2.3258(14) . 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 -0.3(3) . . C1 C2 C3 C4 -0.5(3) . . C2 C3 C4 C5 0.4(3) . . C3 C4 C5 N1 0.5(3) . . C3 C4 C5 C6 -179.43(16) . . N1 C5 C6 N2 -2.2(2) . . C4 C5 C6 N2 177.73(15) . . N2 C7 C8 C9 0.1(3) . . N2 C7 C8 C11 178.65(15) . . C7 C8 C9 O1 -2.3(3) . . C11 C8 C9 O1 179.18(16) . . C7 C8 C9 C10 176.42(17) . . C11 C8 C9 C10 -2.1(3) . . C9 C8 C11 O2 -12.8(3) . . C7 C8 C11 O2 168.61(17) . . C9 C8 C11 O3 167.90(15) . . C7 C8 C11 O3 -10.7(2) . . C4 C5 N1 C1 -1.3(2) . . C6 C5 N1 C1 178.62(15) . . C4 C5 N1 Cu1 -178.41(13) . . C6 C5 N1 Cu1 1.50(18) . . C2 C1 N1 C5 1.2(3) . . C2 C1 N1 Cu1 177.94(13) . . C8 C7 N2 C6 -176.81(15) . . C8 C7 N2 Cu1 3.8(2) . . C5 C6 N2 C7 -177.55(14) . . C5 C6 N2 Cu1 1.91(17) . . C8 C9 O1 Cu1 0.5(3) . . C10 C9 O1 Cu1 -178.34(13) . . O2 C11 O3 C12 -5.0(2) . . C8 C11 O3 C12 174.34(14) . . C13 C12 O3 C11 -172.77(16) . . O12 N11 O11 Cu1 -1.60(7) . . O12 N11 O11 Cu1 178.41(7) 2 . O12 N11 O11 Cu1 178.40(7) . 2 O12 N11 O11 Cu1 -1.59(7) 2 2 O22 N21 O21 Cu1 157.70(10) . . O21 N21 O21 Cu1 -22.30(10) 2 .