#------------------------------------------------------------------------------ #$Date: 2018-01-16 04:34:49 +0200 (Tue, 16 Jan 2018) $ #$Revision: 205237 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229978.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_7229978 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 'C14 H15 Cu N3 O4, 7(H2O)' _chemical_formula_sum 'C14 H29 Cu N3 O11' _chemical_formula_weight 478.94 _chemical_name_common '[CuL30dOAc]' _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 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 95.047(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.8193(4) _cell_length_b 11.6812(6) _cell_length_c 28.7206(16) _cell_measurement_reflns_used 16445 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 26.02 _cell_measurement_theta_min 1.49 _cell_volume 2278.9(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 0.991 _diffrn_measured_fraction_theta_max 0.954 _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 0.0791 _diffrn_reflns_av_unetI/netI 0.0607 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.954 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 25851 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.954 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.515 _diffrn_reflns_theta_min 1.424 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 1.012 _exptl_absorpt_correction_type none _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 948 _exptl_crystal_size_max 0.177 _exptl_crystal_size_mid 0.158 _exptl_crystal_size_min 0.132 _refine_diff_density_max 1.609 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.138 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 5514 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.999 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0567 _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^)+(0.1072P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1517 _refine_ls_wR_factor_ref 0.1665 _reflns_number_gt 3886 _reflns_number_total 5514 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce02007d2.cif _cod_data_source_block cl125 _cod_database_code 7229978 _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 -1 New: P21/c CELL 0.71073 6.8193 11.6812 28.7206 90.000 95.047 90.000 ZERR 4.00 0.0004 0.0006 0.0016 0.000 0.004 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H CU N O UNIT 56 60 4 12 44 MERG 2 FMAP 2 PLAN 10 ACTA BOND $H CONF LIST 4 L.S. 20 TEMP -140.00 WGHT 0.107200 FVAR 0.26112 C1 1 0.782631 0.459450 0.231756 11.00000 0.01697 0.02427 = 0.03166 -0.00150 0.00265 -0.00085 AFIX 43 H1 2 0.747161 0.490002 0.260499 11.00000 -1.20000 AFIX 0 C2 1 0.818635 0.534060 0.196049 11.00000 0.01550 0.02907 = 0.03590 0.00237 0.00117 -0.00066 AFIX 43 H2 2 0.808628 0.614490 0.200131 11.00000 -1.20000 AFIX 0 C3 1 0.869563 0.488691 0.154258 11.00000 0.01907 0.03669 = 0.02910 0.00782 0.00293 -0.00088 AFIX 43 H3 2 0.894824 0.537873 0.129129 11.00000 -1.20000 AFIX 0 C4 1 0.883483 0.370823 0.149309 11.00000 0.02163 0.03775 = 0.02459 0.00093 0.00539 -0.00036 AFIX 43 H4 2 0.919276 0.338244 0.120956 11.00000 -1.20000 AFIX 0 C5 1 0.844266 0.301918 0.186418 11.00000 0.02093 0.02680 = 0.02440 -0.00270 0.00382 -0.00183 C6 1 0.856452 0.173314 0.183911 11.00000 0.04278 0.02843 = 0.02784 -0.00334 0.01329 -0.00133 AFIX 23 H6A 2 0.773731 0.145326 0.156186 11.00000 -1.20000 H6B 2 0.994127 0.149797 0.180755 11.00000 -1.20000 AFIX 0 C7 1 0.758466 0.013315 0.227411 11.00000 0.01730 0.02781 = 0.02545 -0.00551 0.00279 0.00057 AFIX 43 H7 2 0.776963 -0.029214 0.199944 11.00000 -1.20000 AFIX 0 C8 1 0.700667 -0.047392 0.266169 11.00000 0.01870 0.02410 = 0.03008 -0.00413 0.00224 -0.00072 C9 1 0.675575 0.004477 0.309996 11.00000 0.01556 0.02835 = 0.02543 0.00067 0.00162 -0.00057 C10 1 0.625054 -0.019606 0.390061 11.00000 0.02855 0.04269 = 0.02077 0.00143 0.00292 -0.00292 AFIX 23 H10A 2 0.511340 0.033089 0.390035 11.00000 -1.20000 H10B 2 0.746590 0.023663 0.399824 11.00000 -1.20000 AFIX 0 C11 1 0.601065 -0.118186 0.422782 11.00000 0.04512 0.05491 = 0.03449 0.01325 0.00515 -0.00347 AFIX 133 H11A 2 0.469704 -0.151606 0.416260 11.00000 -1.50000 H11B 2 0.616774 -0.090756 0.455141 11.00000 -1.50000 H11C 2 0.701089 -0.176418 0.418260 11.00000 -1.50000 AFIX 0 C12 1 0.669870 -0.166958 0.261568 11.00000 0.01943 0.03024 = 0.03358 -0.00398 0.00725 0.00008 C13 1 0.872589 0.343912 0.349880 11.00000 0.02331 0.03326 = 0.02974 -0.00657 0.00690 -0.01006 C14 1 0.878504 0.404569 0.396170 11.00000 0.03387 0.08950 = 0.04444 -0.03562 0.00828 -0.01370 AFIX 133 H14A 2 0.871482 0.348175 0.421231 11.00000 -1.50000 H14B 2 0.766409 0.457082 0.396119 11.00000 -1.50000 H14C 2 1.001476 0.447978 0.401323 11.00000 -1.50000 AFIX 0 CU1 3 0.738524 0.229884 0.274651 11.00000 0.02091 0.02147 = 0.02092 -0.00262 0.00438 0.00096 N1 4 0.796033 0.345904 0.227203 11.00000 0.01586 0.02546 = 0.02557 -0.00425 0.00319 -0.00066 N2 4 0.788679 0.123387 0.226196 11.00000 0.02741 0.02427 = 0.02164 -0.00205 0.00500 0.00095 N3 4 0.640485 -0.263715 0.257524 11.00000 0.03285 0.02938 = 0.05193 -0.00734 0.01592 -0.00526 O1 5 0.689777 0.108724 0.318895 11.00000 0.02659 0.02295 = 0.02334 -0.00180 0.00352 -0.00151 O2 5 0.636511 -0.068529 0.343731 11.00000 0.02588 0.02660 = 0.02778 0.00284 0.00369 -0.00132 O3 5 0.705013 0.337427 0.325830 11.00000 0.02217 0.02791 = 0.02740 -0.00612 0.00474 0.00088 O4 5 1.025462 0.302937 0.335899 11.00000 0.02159 0.04118 = 0.03172 -0.00711 0.00455 -0.00189 O21 5 0.039823 0.681994 0.443694 11.00000 0.04669 0.04565 = 0.06382 0.00116 0.00883 0.00575 O22 5 0.864521 0.561884 0.044127 11.00000 0.04449 0.04432 = 0.03301 0.00071 0.01100 0.01032 O23 5 0.696470 0.610943 0.483720 11.00000 0.04363 0.04331 = 0.04515 -0.00198 0.00077 -0.01006 O24 5 0.439951 0.214722 0.460717 11.00000 0.04025 0.04299 = 0.03181 0.00412 0.00517 -0.00179 O25 5 0.352896 0.531884 0.435155 11.00000 0.04330 0.05580 = 0.08129 -0.02331 -0.00867 0.01002 O26 5 0.812722 0.147496 0.498144 11.00000 0.03853 0.04134 = 0.04890 0.00058 0.00853 -0.00142 O27 5 0.386631 0.340709 0.379068 11.00000 0.02453 0.03634 = 0.02566 -0.00179 0.00485 -0.00198 HKLF 4 REM SIR97 run in space group P -1 New: P21/c REM R1 = 0.0567 for 3886 Fo > 4sig(Fo) and 0.0824 for all 5514 data REM 262 parameters refined using 0 restraints END WGHT 0.1072 0.0000 REM Highest difference peak 1.609, deepest hole -0.551, 1-sigma level 0.138 Q1 1 0.4030 0.5708 0.4096 11.00000 0.05 1.61 Q2 1 0.6988 0.6407 0.3580 11.00000 0.05 1.21 Q3 1 0.1060 0.6139 0.4724 11.00000 0.05 0.90 Q4 1 0.7040 0.1663 0.4806 11.00000 0.05 0.69 Q5 1 0.4307 0.2565 0.4332 11.00000 0.05 0.65 Q6 1 0.8492 0.5026 0.0351 11.00000 0.05 0.61 Q7 1 0.4781 0.5580 0.4552 11.00000 0.05 0.61 Q8 1 0.9684 0.5883 0.0370 11.00000 0.05 0.60 Q9 1 0.4717 0.3351 0.3626 11.00000 0.05 0.58 Q10 1 0.1559 0.6412 0.4416 11.00000 0.05 0.57 ; _shelx_res_checksum 49779 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 0.7826(5) 0.4594(3) 0.23176(12) 0.0243(7) Uani 1 1 d . . H1 H 0.7472 0.4900 0.2605 0.029 Uiso 1 1 calc R U C2 C 0.8186(5) 0.5341(3) 0.19605(13) 0.0269(7) Uani 1 1 d . . H2 H 0.8086 0.6145 0.2001 0.032 Uiso 1 1 calc R U C3 C 0.8696(5) 0.4887(3) 0.15426(13) 0.0282(7) Uani 1 1 d . . H3 H 0.8948 0.5379 0.1291 0.034 Uiso 1 1 calc R U C4 C 0.8835(5) 0.3708(3) 0.14931(12) 0.0278(7) Uani 1 1 d . . H4 H 0.9193 0.3382 0.1210 0.033 Uiso 1 1 calc R U C5 C 0.8443(5) 0.3019(3) 0.18642(12) 0.0239(6) Uani 1 1 d . . C6 C 0.8565(6) 0.1733(3) 0.18391(13) 0.0324(8) Uani 1 1 d . . H6A H 0.7737 0.1453 0.1562 0.039 Uiso 1 1 calc R U H6B H 0.9941 0.1498 0.1808 0.039 Uiso 1 1 calc R U C7 C 0.7585(5) 0.0133(3) 0.22741(12) 0.0235(6) Uani 1 1 d . . H7 H 0.7770 -0.0292 0.1999 0.028 Uiso 1 1 calc R U C8 C 0.7007(5) -0.0474(3) 0.26617(12) 0.0243(7) Uani 1 1 d . . C9 C 0.6756(5) 0.0045(3) 0.31000(12) 0.0231(6) Uani 1 1 d . . C10 C 0.6251(6) -0.0196(3) 0.39006(12) 0.0306(7) Uani 1 1 d . . H10A H 0.5113 0.0331 0.3900 0.037 Uiso 1 1 calc R U H10B H 0.7466 0.0237 0.3998 0.037 Uiso 1 1 calc R U C11 C 0.6011(7) -0.1182(4) 0.42278(15) 0.0447(10) Uani 1 1 d . . H11A H 0.4697 -0.1516 0.4163 0.067 Uiso 1 1 calc R U H11B H 0.6168 -0.0908 0.4551 0.067 Uiso 1 1 calc R U H11C H 0.7011 -0.1764 0.4183 0.067 Uiso 1 1 calc R U C12 C 0.6699(5) -0.1670(3) 0.26157(13) 0.0275(7) Uani 1 1 d . . C13 C 0.8726(5) 0.3439(3) 0.34988(12) 0.0285(7) Uani 1 1 d . . C14 C 0.8785(7) 0.4046(5) 0.39617(17) 0.0556(14) Uani 1 1 d . . H14A H 0.8715 0.3482 0.4212 0.083 Uiso 1 1 calc R U H14B H 0.7664 0.4571 0.3961 0.083 Uiso 1 1 calc R U H14C H 1.0015 0.4480 0.4013 0.083 Uiso 1 1 calc R U Cu1 Cu 0.73852(6) 0.22988(3) 0.27465(2) 0.02095(14) Uani 1 1 d . . N1 N 0.7960(4) 0.3459(2) 0.22720(9) 0.0222(5) Uani 1 1 d . . N2 N 0.7887(4) 0.1234(2) 0.22620(9) 0.0243(6) Uani 1 1 d . . N3 N 0.6405(5) -0.2637(3) 0.25752(13) 0.0373(8) Uani 1 1 d . . O1 O 0.6898(3) 0.10872(19) 0.31890(8) 0.0242(5) Uani 1 1 d . . O2 O 0.6365(3) -0.0685(2) 0.34373(8) 0.0267(5) Uani 1 1 d . . O3 O 0.7050(3) 0.3374(2) 0.32583(8) 0.0257(5) Uani 1 1 d . . O4 O 1.0255(4) 0.3029(2) 0.33590(9) 0.0314(5) Uani 1 1 d . . O21 O 0.0398(5) 0.6820(3) 0.44369(13) 0.0518(8) Uani 1 1 d . . O22 O 0.8645(4) 0.5619(3) 0.04413(10) 0.0402(7) Uani 1 1 d . . O23 O 0.6965(5) 0.6109(3) 0.48372(11) 0.0442(7) Uani 1 1 d . . O24 O 0.4400(4) 0.2147(2) 0.46072(10) 0.0382(6) Uani 1 1 d . . O25 O 0.3529(5) 0.5319(3) 0.43516(14) 0.0610(10) Uani 1 1 d . . O26 O 0.8127(4) 0.1475(3) 0.49814(11) 0.0426(7) Uani 1 1 d . . O27 O 0.3866(4) 0.3407(2) 0.37907(8) 0.0287(5) 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 0.0170(15) 0.0243(17) 0.0317(18) -0.0015(12) 0.0026(13) -0.0008(11) C2 0.0155(15) 0.0291(17) 0.0359(19) 0.0024(13) 0.0012(13) -0.0007(12) C3 0.0191(16) 0.0367(19) 0.0291(18) 0.0078(14) 0.0029(13) -0.0009(13) C4 0.0216(16) 0.0378(19) 0.0246(16) 0.0009(14) 0.0054(13) -0.0004(13) C5 0.0209(15) 0.0268(16) 0.0244(16) -0.0027(12) 0.0038(12) -0.0018(12) C6 0.043(2) 0.0284(18) 0.0278(18) -0.0033(14) 0.0133(15) -0.0013(15) C7 0.0173(15) 0.0278(17) 0.0255(16) -0.0055(12) 0.0028(12) 0.0006(12) C8 0.0187(15) 0.0241(16) 0.0301(17) -0.0041(12) 0.0022(12) -0.0007(11) C9 0.0156(15) 0.0284(17) 0.0254(16) 0.0007(12) 0.0016(12) -0.0006(11) C10 0.0286(18) 0.043(2) 0.0208(17) 0.0014(14) 0.0029(13) -0.0029(14) C11 0.045(2) 0.055(3) 0.034(2) 0.0133(18) 0.0052(18) -0.0035(19) C12 0.0194(16) 0.0302(19) 0.0336(18) -0.0040(13) 0.0072(13) 0.0001(12) C13 0.0233(17) 0.0333(18) 0.0297(17) -0.0066(13) 0.0069(13) -0.0101(13) C14 0.034(2) 0.089(4) 0.044(3) -0.036(2) 0.0083(19) -0.014(2) Cu1 0.0209(2) 0.0215(2) 0.0209(2) -0.00262(14) 0.00438(14) 0.00096(14) N1 0.0159(13) 0.0255(14) 0.0256(14) -0.0042(10) 0.0032(10) -0.0007(10) N2 0.0274(15) 0.0243(14) 0.0216(13) -0.0020(10) 0.0050(11) 0.0010(11) N3 0.0328(17) 0.0294(16) 0.052(2) -0.0073(14) 0.0159(15) -0.0053(13) O1 0.0266(12) 0.0230(11) 0.0233(11) -0.0018(9) 0.0035(9) -0.0015(9) O2 0.0259(12) 0.0266(12) 0.0278(12) 0.0028(9) 0.0037(9) -0.0013(9) O3 0.0222(12) 0.0279(12) 0.0274(12) -0.0061(9) 0.0047(9) 0.0009(9) O4 0.0216(12) 0.0412(14) 0.0317(13) -0.0071(11) 0.0046(10) -0.0019(10) O21 0.0467(19) 0.0457(18) 0.064(2) 0.0012(15) 0.0088(15) 0.0057(14) O22 0.0445(16) 0.0443(16) 0.0330(15) 0.0007(12) 0.0110(12) 0.0103(13) O23 0.0436(17) 0.0433(17) 0.0451(17) -0.0020(13) 0.0008(13) -0.0101(13) O24 0.0402(16) 0.0430(17) 0.0318(14) 0.0041(11) 0.0052(12) -0.0018(12) O25 0.0433(19) 0.056(2) 0.081(3) -0.0233(18) -0.0087(17) 0.0100(15) O26 0.0385(16) 0.0413(16) 0.0489(17) 0.0006(13) 0.0085(13) -0.0014(12) O27 0.0245(12) 0.0363(14) 0.0257(12) -0.0018(10) 0.0048(9) -0.0020(10) 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' Cu Cu 0.3201 1.2651 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 C2 122.3(3) N1 C1 H1 118.9 C2 C1 H1 118.9 C3 C2 C1 118.4(3) C3 C2 H2 120.8 C1 C2 H2 120.8 C2 C3 C4 119.6(3) C2 C3 H3 120.2 C4 C3 H3 120.2 C5 C4 C3 118.7(3) C5 C4 H4 120.7 C3 C4 H4 120.7 N1 C5 C4 121.9(3) N1 C5 C6 116.2(3) C4 C5 C6 122.0(3) N2 C6 C5 109.6(3) 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 125.1(3) N2 C7 H7 117.4 C8 C7 H7 117.4 C7 C8 C12 118.2(3) C7 C8 C9 123.4(3) C12 C8 C9 118.3(3) O1 C9 O2 119.5(3) O1 C9 C8 125.8(3) O2 C9 C8 114.7(3) O2 C10 C11 106.7(3) O2 C10 H10A 110.4 C11 C10 H10A 110.4 O2 C10 H10B 110.4 C11 C10 H10B 110.4 H10A C10 H10B 108.6 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 178.5(4) O4 C13 O3 122.3(3) O4 C13 C14 120.5(3) O3 C13 C14 117.2(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 N2 Cu1 O1 93.07(11) N2 Cu1 O3 176.29(11) O1 Cu1 O3 86.49(10) N2 Cu1 N1 83.47(12) O1 Cu1 N1 176.39(10) O3 Cu1 N1 96.90(11) C1 N1 C5 119.2(3) C1 N1 Cu1 126.2(2) C5 N1 Cu1 114.5(2) C7 N2 C6 118.6(3) C7 N2 Cu1 125.5(2) C6 N2 Cu1 115.7(2) C9 O1 Cu1 126.2(2) C9 O2 C10 116.3(3) C13 O3 Cu1 106.5(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.337(4) C1 C2 1.384(5) C1 H1 0.9500 C2 C3 1.384(5) C2 H2 0.9500 C3 C4 1.388(5) C3 H3 0.9500 C4 C5 1.380(5) C4 H4 0.9500 C5 N1 1.346(4) C5 C6 1.507(5) C6 N2 1.459(4) C6 H6A 0.9900 C6 H6B 0.9900 C7 N2 1.303(5) C7 C8 1.405(5) C7 H7 0.9500 C8 C12 1.417(5) C8 C9 1.421(5) C9 O1 1.246(4) C9 O2 1.335(4) C10 O2 1.457(4) C10 C11 1.504(5) C10 H10A 0.9900 C10 H10B 0.9900 C11 H11A 0.9800 C11 H11B 0.9800 C11 H11C 0.9800 C12 N3 1.152(5) C13 O4 1.245(4) C13 O3 1.284(4) C13 C14 1.504(5) C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 Cu1 N2 1.920(3) Cu1 O1 1.950(2) Cu1 O3 1.962(2) Cu1 N1 1.985(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 N1 C1 C2 C3 0.2(5) C1 C2 C3 C4 -0.1(5) C2 C3 C4 C5 0.5(5) C3 C4 C5 N1 -1.0(5) C3 C4 C5 C6 -179.9(3) N1 C5 C6 N2 6.7(4) C4 C5 C6 N2 -174.4(3) N2 C7 C8 C12 178.7(3) N2 C7 C8 C9 -2.7(5) C7 C8 C9 O1 4.4(5) C12 C8 C9 O1 -177.0(3) C7 C8 C9 O2 -174.6(3) C12 C8 C9 O2 4.1(4) C2 C1 N1 C5 -0.7(5) C2 C1 N1 Cu1 -177.5(2) C4 C5 N1 C1 1.1(5) C6 C5 N1 C1 -180.0(3) C4 C5 N1 Cu1 178.3(3) C6 C5 N1 Cu1 -2.8(4) C8 C7 N2 C6 177.4(3) C8 C7 N2 Cu1 -6.0(5) C5 C6 N2 C7 169.2(3) C5 C6 N2 Cu1 -7.7(4) O2 C9 O1 Cu1 -178.2(2) C8 C9 O1 Cu1 2.9(5) O1 C9 O2 C10 -3.6(4) C8 C9 O2 C10 175.4(3) C11 C10 O2 C9 -174.3(3) O4 C13 O3 Cu1 11.1(4) C14 C13 O3 Cu1 -169.4(3)