#------------------------------------------------------------------------------ #$Date: 2018-01-16 04:34:49 +0200 (Tue, 16 Jan 2018) $ #$Revision: 205237 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229975.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_7229975 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 'C36 H34 Cu2 N6 O12' _chemical_formula_sum 'C36 H34 Cu2 N6 O12' _chemical_formula_weight 869.76 _chemical_name_common '[CuL30fNO3]' _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 97.713(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.2653(4) _cell_length_b 8.8823(4) _cell_length_c 20.2634(9) _cell_measurement_reflns_used 9119 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 28.45 _cell_measurement_theta_min 2.03 _cell_volume 1830.89(14) _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 0.982 _diffrn_measured_fraction_theta_max 0.934 _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 0.0405 _diffrn_reflns_av_unetI/netI 0.0481 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.934 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 13069 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.934 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.489 _diffrn_reflns_theta_min 2.028 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 1.235 _exptl_absorpt_correction_type none _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 892 _exptl_crystal_size_max 0.163 _exptl_crystal_size_mid 0.136 _exptl_crystal_size_min 0.134 _refine_diff_density_max 0.286 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 4324 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.913 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0314 _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^)+(0.0356P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.0726 _reflns_number_gt 3240 _reflns_number_total 4324 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce02007d2.cif _cod_data_source_block cl108 _cod_database_code 7229975 _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/n CELL 0.71073 10.2653 8.8823 20.2634 90.000 97.713 90.000 ZERR 4.00 0.0004 0.0004 0.0009 0.000 0.003 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O CU UNIT 72 68 12 24 4 MERG 2 FMAP 2 PLAN 10 ACTA BOND $H CONF LIST 4 L.S. 20 HTAB TEMP -140.00 WGHT 0.035600 FVAR 0.49508 CU1 5 0.072383 0.329599 0.483407 11.00000 0.02927 0.02454 = 0.02825 0.00528 0.00797 0.01021 O3 4 0.485380 0.246148 0.350963 11.00000 0.02934 0.03948 = 0.03010 0.00183 0.00737 0.01383 O2 4 0.567816 0.146671 0.449196 11.00000 0.03001 0.04705 = 0.04255 0.01494 0.00684 0.01642 O11 4 -0.081595 0.452306 0.446220 11.00000 0.03179 0.03265 = 0.02629 0.00464 0.00732 0.01130 O12 4 -0.075195 0.350209 0.348788 11.00000 0.04898 0.04313 = 0.04176 -0.01240 0.00792 0.01210 O1 4 0.177353 0.435239 0.427732 11.00000 0.03063 0.02871 = 0.03577 0.00776 0.01087 0.01195 C15 1 0.253114 0.574412 0.316199 11.00000 0.02829 0.02769 = 0.02885 -0.00188 0.00577 0.00515 AFIX 43 H15 2 0.164469 0.540786 0.309572 11.00000 -1.20000 AFIX 0 N1 3 -0.028568 0.203572 0.538937 11.00000 0.03377 0.02061 = 0.02614 0.00028 0.00707 0.00609 O13 4 -0.176610 0.560419 0.357193 11.00000 0.07292 0.05031 = 0.04241 0.00614 -0.00719 0.03188 N2 3 0.215555 0.202489 0.518157 11.00000 0.03016 0.02473 = 0.02536 0.00166 0.00535 0.00877 C10 1 0.341425 0.512703 0.367699 11.00000 0.02863 0.02274 = 0.02943 -0.00162 0.00608 0.00693 C8 1 0.363784 0.275967 0.440441 11.00000 0.02498 0.02577 = 0.02608 -0.00103 0.00260 0.00658 C9 1 0.291361 0.400700 0.413051 11.00000 0.02598 0.02649 = 0.02548 -0.00332 0.00262 0.00452 C16 1 0.482871 0.218487 0.415410 11.00000 0.02745 0.02637 = 0.03232 0.00064 0.00368 0.00529 C2 1 -0.218851 0.121372 0.584225 11.00000 0.03760 0.02999 = 0.03413 -0.00367 0.00769 -0.00217 AFIX 43 H2 2 -0.310572 0.129761 0.586009 11.00000 -1.20000 AFIX 0 N11 3 -0.111842 0.454061 0.381229 11.00000 0.03397 0.02948 = 0.03163 0.00196 0.00391 0.00629 C11 1 0.469493 0.566155 0.377726 11.00000 0.02955 0.03038 = 0.04656 0.00130 0.00218 0.00350 AFIX 43 H11 2 0.530027 0.527518 0.413269 11.00000 -1.20000 AFIX 0 C5 1 0.044517 0.101959 0.577098 11.00000 0.03777 0.02198 = 0.02131 -0.00382 0.00416 0.00497 C1 1 -0.158507 0.212563 0.542832 11.00000 0.03327 0.02555 = 0.03146 -0.00230 0.00690 0.00467 AFIX 43 H1 2 -0.209891 0.284352 0.516050 11.00000 -1.20000 AFIX 0 C4 1 -0.010741 0.005951 0.619172 11.00000 0.04555 0.02468 = 0.02613 0.00241 0.00102 0.00003 AFIX 43 H4 2 0.041939 -0.066552 0.644857 11.00000 -1.20000 AFIX 0 C7 1 0.325286 0.189665 0.493408 11.00000 0.02857 0.02428 = 0.02592 -0.00197 -0.00036 0.00776 AFIX 43 H7 2 0.385452 0.115467 0.512595 11.00000 -1.20000 AFIX 0 C17 1 0.605146 0.204003 0.324448 11.00000 0.03811 0.04979 = 0.04062 0.00594 0.01587 0.01586 AFIX 23 H17A 2 0.607091 0.093976 0.316840 11.00000 -1.20000 H17B 2 0.683316 0.232096 0.356133 11.00000 -1.20000 AFIX 0 C13 1 0.422594 0.733730 0.284503 11.00000 0.04929 0.03046 = 0.05071 0.00688 0.02230 0.00378 AFIX 43 H13 2 0.451284 0.807594 0.255757 11.00000 -1.20000 AFIX 0 C6 1 0.189078 0.102465 0.571876 11.00000 0.03742 0.02545 = 0.02559 0.00367 0.00383 0.00902 AFIX 23 H6A 2 0.238696 0.136881 0.614479 11.00000 -1.20000 H6B 2 0.218353 -0.000879 0.562963 11.00000 -1.20000 AFIX 0 C3 1 -0.143709 0.016632 0.623463 11.00000 0.04790 0.03010 = 0.03039 0.00239 0.00587 -0.00868 AFIX 43 H3 2 -0.183163 -0.046881 0.652883 11.00000 -1.20000 AFIX 0 C12 1 0.509325 0.675270 0.336260 11.00000 0.03216 0.03534 = 0.06715 0.00306 0.01338 -0.00325 AFIX 43 H12 2 0.597429 0.710649 0.343369 11.00000 -1.20000 AFIX 0 C14 1 0.293501 0.683835 0.274841 11.00000 0.04379 0.03216 = 0.03147 0.00326 0.00989 0.00770 AFIX 43 H14 2 0.232898 0.724724 0.239879 11.00000 -1.20000 AFIX 0 C18 1 0.604976 0.286801 0.260114 11.00000 0.05676 0.06617 = 0.03835 0.00749 0.01834 0.01179 AFIX 133 H18A 2 0.528063 0.256575 0.228949 11.00000 -1.50000 H18B 2 0.685270 0.262646 0.241035 11.00000 -1.50000 H18C 2 0.601484 0.395402 0.268229 11.00000 -1.50000 AFIX 0 HKLF 4 REM SIR97 run in space group P 21/n REM R1 = 0.0314 for 3240 Fo > 4sig(Fo) and 0.0487 for all 4324 data REM 253 parameters refined using 0 restraints END WGHT 0.0356 0.0000 REM Instructions for potential hydrogen bonds HTAB C1 O11 EQIV $1 -x, -y, -z+1 HTAB C4 O12_$1 EQIV $2 -x+1, -y, -z+1 HTAB C7 O2_$2 HTAB C6 O2_$2 REM Highest difference peak 0.286, deepest hole -0.429, 1-sigma level 0.057 Q1 1 0.4068 0.2435 0.4240 11.00000 0.05 0.29 Q2 1 0.3293 0.3109 0.4239 11.00000 0.05 0.27 Q3 1 0.2571 0.1811 0.4925 11.00000 0.05 0.27 Q4 1 0.0636 0.2416 0.4559 11.00000 0.05 0.27 Q5 1 0.0821 0.4363 0.5126 11.00000 0.05 0.26 Q6 1 0.0863 0.2439 0.5096 11.00000 0.05 0.25 Q7 1 0.3398 0.2522 0.4709 11.00000 0.05 0.25 Q8 1 0.3164 0.4440 0.3835 11.00000 0.05 0.25 Q9 1 -0.0013 0.1530 0.5639 11.00000 0.05 0.24 Q10 1 0.0040 0.0370 0.5864 11.00000 0.05 0.24 ; _shelx_res_checksum 25248 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 Cu1 Cu 0.07238(2) 0.32960(3) 0.48341(2) 0.02698(8) Uani 1 1 d . . O3 O 0.48538(13) 0.24615(18) 0.35096(7) 0.0327(3) Uani 1 1 d . . O2 O 0.56782(14) 0.14667(19) 0.44920(8) 0.0397(4) Uani 1 1 d . . O11 O -0.08160(13) 0.45231(17) 0.44622(7) 0.0299(3) Uani 1 1 d . . O12 O -0.07520(16) 0.3502(2) 0.34879(8) 0.0445(4) Uani 1 1 d . . O1 O 0.17735(13) 0.43524(16) 0.42773(7) 0.0311(3) Uani 1 1 d . . C15 C 0.25311(19) 0.5744(2) 0.31620(10) 0.0281(4) Uani 1 1 d . . H15 H 0.1645 0.5408 0.3096 0.034 Uiso 1 1 calc R U N1 N -0.02857(16) 0.20357(18) 0.53894(8) 0.0266(4) Uani 1 1 d . . O13 O -0.17661(19) 0.5604(2) 0.35719(9) 0.0566(5) Uani 1 1 d . . N2 N 0.21555(15) 0.20249(19) 0.51816(8) 0.0266(4) Uani 1 1 d . . C10 C 0.34142(18) 0.5127(2) 0.36770(10) 0.0267(4) Uani 1 1 d . . C8 C 0.36378(18) 0.2760(2) 0.44044(9) 0.0257(4) Uani 1 1 d . . C9 C 0.29136(18) 0.4007(2) 0.41305(9) 0.0261(4) Uani 1 1 d . . C16 C 0.48287(18) 0.2185(2) 0.41541(10) 0.0287(4) Uani 1 1 d . . C2 C -0.2189(2) 0.1214(3) 0.58422(11) 0.0336(5) Uani 1 1 d . . H2 H -0.3106 0.1298 0.5860 0.040 Uiso 1 1 calc R U N11 N -0.11184(16) 0.4541(2) 0.38123(9) 0.0317(4) Uani 1 1 d . . C11 C 0.4695(2) 0.5662(3) 0.37773(12) 0.0358(5) Uani 1 1 d . . H11 H 0.5300 0.5275 0.4133 0.043 Uiso 1 1 calc R U C5 C 0.04452(19) 0.1020(2) 0.57710(9) 0.0270(4) Uani 1 1 d . . C1 C -0.1585(2) 0.2126(2) 0.54283(10) 0.0299(4) Uani 1 1 d . . H1 H -0.2099 0.2844 0.5161 0.036 Uiso 1 1 calc R U C4 C -0.0107(2) 0.0060(2) 0.61917(10) 0.0325(5) Uani 1 1 d . . H4 H 0.0419 -0.0666 0.6449 0.039 Uiso 1 1 calc R U C7 C 0.32529(18) 0.1897(2) 0.49341(9) 0.0266(4) Uani 1 1 d . . H7 H 0.3855 0.1155 0.5126 0.032 Uiso 1 1 calc R U C17 C 0.6051(2) 0.2040(3) 0.32445(12) 0.0419(6) Uani 1 1 d . . H17A H 0.6071 0.0940 0.3168 0.050 Uiso 1 1 calc R U H17B H 0.6833 0.2321 0.3561 0.050 Uiso 1 1 calc R U C13 C 0.4226(2) 0.7337(3) 0.28450(13) 0.0421(5) Uani 1 1 d . . H13 H 0.4513 0.8076 0.2558 0.050 Uiso 1 1 calc R U C6 C 0.18908(19) 0.1025(2) 0.57188(10) 0.0295(4) Uani 1 1 d . . H6A H 0.2387 0.1369 0.6145 0.035 Uiso 1 1 calc R U H6B H 0.2184 -0.0009 0.5630 0.035 Uiso 1 1 calc R U C3 C -0.1437(2) 0.0166(3) 0.62346(11) 0.0361(5) Uani 1 1 d . . H3 H -0.1832 -0.0469 0.6529 0.043 Uiso 1 1 calc R U C12 C 0.5093(2) 0.6753(3) 0.33626(14) 0.0443(6) Uani 1 1 d . . H12 H 0.5974 0.7106 0.3434 0.053 Uiso 1 1 calc R U C14 C 0.2935(2) 0.6838(3) 0.27484(11) 0.0354(5) Uani 1 1 d . . H14 H 0.2329 0.7247 0.2399 0.042 Uiso 1 1 calc R U C18 C 0.6050(3) 0.2868(4) 0.26011(13) 0.0527(7) Uani 1 1 d . . H18A H 0.5281 0.2566 0.2289 0.079 Uiso 1 1 calc R U H18B H 0.6853 0.2626 0.2410 0.079 Uiso 1 1 calc R U H18C H 0.6015 0.3954 0.2682 0.079 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 0.02927(13) 0.02454(13) 0.02825(12) 0.00528(11) 0.00797(8) 0.01021(10) O3 0.0293(7) 0.0395(9) 0.0301(8) 0.0018(6) 0.0074(5) 0.0138(6) O2 0.0300(7) 0.0470(10) 0.0426(9) 0.0149(7) 0.0068(6) 0.0164(7) O11 0.0318(7) 0.0326(8) 0.0263(7) 0.0046(6) 0.0073(5) 0.0113(6) O12 0.0490(9) 0.0431(10) 0.0418(9) -0.0124(8) 0.0079(7) 0.0121(7) O1 0.0306(7) 0.0287(8) 0.0358(8) 0.0078(6) 0.0109(6) 0.0120(6) C15 0.0283(10) 0.0277(11) 0.0288(10) -0.0019(8) 0.0058(7) 0.0051(8) N1 0.0338(9) 0.0206(9) 0.0261(8) 0.0003(6) 0.0071(6) 0.0061(6) O13 0.0729(12) 0.0503(11) 0.0424(10) 0.0061(8) -0.0072(8) 0.0319(9) N2 0.0302(8) 0.0247(9) 0.0254(8) 0.0017(6) 0.0054(6) 0.0088(6) C10 0.0286(10) 0.0227(10) 0.0294(10) -0.0016(8) 0.0061(7) 0.0069(8) C8 0.0250(9) 0.0258(10) 0.0261(10) -0.0010(8) 0.0026(7) 0.0066(7) C9 0.0260(10) 0.0265(10) 0.0255(9) -0.0033(8) 0.0026(7) 0.0045(8) C16 0.0274(10) 0.0264(10) 0.0323(11) 0.0006(8) 0.0037(7) 0.0053(8) C2 0.0376(11) 0.0300(12) 0.0341(11) -0.0037(9) 0.0077(8) -0.0022(9) N11 0.0340(9) 0.0295(10) 0.0316(9) 0.0020(7) 0.0039(7) 0.0063(7) C11 0.0296(11) 0.0304(12) 0.0466(13) 0.0013(10) 0.0022(8) 0.0035(8) C5 0.0378(11) 0.0220(10) 0.0213(9) -0.0038(8) 0.0042(7) 0.0050(8) C1 0.0333(10) 0.0256(11) 0.0315(10) -0.0023(8) 0.0069(8) 0.0047(8) C4 0.0456(12) 0.0247(11) 0.0261(10) 0.0024(8) 0.0010(8) 0.0000(9) C7 0.0286(10) 0.0243(11) 0.0259(9) -0.0020(8) -0.0004(7) 0.0078(7) C17 0.0381(12) 0.0498(15) 0.0406(12) 0.0059(11) 0.0159(9) 0.0159(10) C13 0.0493(14) 0.0305(12) 0.0507(14) 0.0069(11) 0.0223(10) 0.0038(10) C6 0.0374(11) 0.0254(10) 0.0256(10) 0.0037(8) 0.0038(8) 0.0090(8) C3 0.0479(13) 0.0301(12) 0.0304(11) 0.0024(9) 0.0059(9) -0.0087(9) C12 0.0322(11) 0.0353(13) 0.0672(16) 0.0031(12) 0.0134(10) -0.0033(10) C14 0.0438(12) 0.0322(12) 0.0315(11) 0.0033(9) 0.0099(8) 0.0077(9) C18 0.0568(16) 0.0662(19) 0.0384(14) 0.0075(12) 0.0183(11) 0.0118(13) 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_3 O1 Cu1 N2 92.35(6) . O1 Cu1 N1 174.90(6) . N2 Cu1 N1 83.78(7) . O1 Cu1 O11 89.41(6) . N2 Cu1 O11 177.12(7) . N1 Cu1 O11 94.33(6) . O1 Cu1 O11 88.51(6) 3_566 N2 Cu1 O11 106.91(6) 3_566 N1 Cu1 O11 95.78(6) 3_566 O11 Cu1 O11 75.41(6) 3_566 C16 O3 C17 116.29(15) . N11 O11 Cu1 117.20(11) . N11 O11 Cu1 124.89(12) 3_566 Cu1 O11 Cu1 104.59(6) 3_566 C9 O1 Cu1 128.66(13) . C14 C15 C10 120.70(19) . C14 C15 H15 119.7 . C10 C15 H15 119.7 . C5 N1 C1 118.96(18) . C5 N1 Cu1 114.30(13) . C1 N1 Cu1 126.72(13) . C7 N2 C6 119.55(16) . C7 N2 Cu1 125.01(14) . C6 N2 Cu1 115.07(12) . C11 C10 C15 118.8(2) . C11 C10 C9 122.43(17) . C15 C10 C9 118.59(17) . C9 C8 C7 122.58(17) . C9 C8 C16 123.73(18) . C7 C8 C16 113.64(16) . O1 C9 C8 123.18(19) . O1 C9 C10 112.57(16) . C8 C9 C10 124.12(17) . O2 C16 O3 122.84(19) . O2 C16 C8 123.57(19) . O3 C16 C8 113.51(15) . C1 C2 C3 118.9(2) . C1 C2 H2 120.5 . C3 C2 H2 120.5 . O13 N11 O12 124.16(18) . O13 N11 O11 116.96(17) . O12 N11 O11 118.88(16) . C12 C11 C10 120.2(2) . C12 C11 H11 119.9 . C10 C11 H11 119.9 . N1 C5 C4 121.62(18) . N1 C5 C6 115.87(18) . C4 C5 C6 122.49(18) . N1 C1 C2 122.13(19) . N1 C1 H1 118.9 . C2 C1 H1 118.9 . C5 C4 C3 119.17(19) . C5 C4 H4 120.4 . C3 C4 H4 120.4 . N2 C7 C8 126.13(17) . N2 C7 H7 116.9 . C8 C7 H7 116.9 . O3 C17 C18 107.03(18) . O3 C17 H17A 110.3 . C18 C17 H17A 110.3 . O3 C17 H17B 110.3 . C18 C17 H17B 110.3 . H17A C17 H17B 108.6 . C12 C13 C14 119.5(2) . C12 C13 H13 120.2 . C14 C13 H13 120.2 . N2 C6 C5 109.83(15) . 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 . C4 C3 C2 119.2(2) . C4 C3 H3 120.4 . C2 C3 H3 120.4 . C11 C12 C13 120.8(2) . C11 C12 H12 119.6 . C13 C12 H12 119.6 . C15 C14 C13 119.9(2) . C15 C14 H14 120.1 . C13 C14 H14 120.1 . C17 C18 H18A 109.5 . C17 C18 H18B 109.5 . H18A C18 H18B 109.5 . C17 C18 H18C 109.5 . H18A C18 H18C 109.5 . H18B C18 H18C 109.5 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cu1 O1 1.9080(15) . Cu1 N2 1.9112(15) . Cu1 N1 1.9764(17) . Cu1 O11 1.9835(13) . Cu1 O11 2.3997(15) 3_566 O3 C16 1.332(2) . O3 C17 1.455(2) . O2 C16 1.215(2) . O11 N11 1.312(2) . O11 Cu1 2.3998(15) 3_566 O12 N11 1.221(2) . O1 C9 1.283(2) . C15 C14 1.383(3) . C15 C10 1.399(3) . C15 H15 0.9500 . N1 C5 1.349(2) . N1 C1 1.349(3) . O13 N11 1.219(2) . N2 C7 1.298(3) . N2 C6 1.459(3) . C10 C11 1.387(3) . C10 C9 1.492(3) . C8 C9 1.406(3) . C8 C7 1.418(3) . C8 C16 1.476(3) . C2 C1 1.372(3) . C2 C3 1.389(3) . C2 H2 0.9500 . C11 C12 1.380(3) . C11 H11 0.9500 . C5 C4 1.380(3) . C5 C6 1.502(3) . C1 H1 0.9500 . C4 C3 1.383(3) . C4 H4 0.9500 . C7 H7 0.9500 . C17 C18 1.497(3) . C17 H17A 0.9900 . C17 H17B 0.9900 . C13 C12 1.383(3) . C13 C14 1.386(3) . C13 H13 0.9500 . C6 H6A 0.9900 . C6 H6B 0.9900 . C3 H3 0.9500 . C12 H12 0.9500 . C14 H14 0.9500 . C18 H18A 0.9800 . C18 H18B 0.9800 . C18 H18C 0.9800 . 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 C14 C15 C10 C11 1.7(3) . C14 C15 C10 C9 176.94(18) . Cu1 O1 C9 C8 -3.8(3) . Cu1 O1 C9 C10 -179.94(12) . C7 C8 C9 O1 -8.9(3) . C16 C8 C9 O1 168.42(18) . C7 C8 C9 C10 166.79(18) . C16 C8 C9 C10 -15.9(3) . C11 C10 C9 O1 135.4(2) . C15 C10 C9 O1 -39.6(3) . C11 C10 C9 C8 -40.7(3) . C15 C10 C9 C8 144.3(2) . C17 O3 C16 O2 -8.4(3) . C17 O3 C16 C8 174.88(18) . C9 C8 C16 O2 155.5(2) . C7 C8 C16 O2 -27.0(3) . C9 C8 C16 O3 -27.8(3) . C7 C8 C16 O3 149.77(18) . Cu1 O11 N11 O13 -157.96(16) . Cu1 O11 N11 O13 -23.2(2) 3_566 Cu1 O11 N11 O12 22.7(2) . Cu1 O11 N11 O12 157.40(14) 3_566 C15 C10 C11 C12 -1.8(3) . C9 C10 C11 C12 -176.8(2) . C1 N1 C5 C4 0.9(3) . Cu1 N1 C5 C4 179.50(15) . C1 N1 C5 C6 -177.86(17) . Cu1 N1 C5 C6 0.7(2) . C5 N1 C1 C2 -0.2(3) . Cu1 N1 C1 C2 -178.58(15) . C3 C2 C1 N1 0.1(3) . N1 C5 C4 C3 -1.5(3) . C6 C5 C4 C3 177.14(19) . C6 N2 C7 C8 178.59(19) . Cu1 N2 C7 C8 5.9(3) . C9 C8 C7 N2 7.7(3) . C16 C8 C7 N2 -169.85(19) . C16 O3 C17 C18 -162.3(2) . C7 N2 C6 C5 -161.61(17) . Cu1 N2 C6 C5 11.7(2) . N1 C5 C6 N2 -7.9(2) . C4 C5 C6 N2 173.35(18) . C5 C4 C3 C2 1.4(3) . C1 C2 C3 C4 -0.7(3) . C10 C11 C12 C13 0.4(4) . C14 C13 C12 C11 1.1(4) . C10 C15 C14 C13 -0.3(3) . C12 C13 C14 C15 -1.1(3) .