#------------------------------------------------------------------------------ #$Date: 2018-01-16 04:34:49 +0200 (Tue, 16 Jan 2018) $ #$Revision: 205237 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229977.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_7229977 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 H17 Cu N3 O3 S' _chemical_formula_sum 'C14 H17 Cu N3 O3 S' _chemical_formula_weight 370.90 _chemical_name_common '[CuL30bSCN]' _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 92.590(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.8474(5) _cell_length_b 15.5449(6) _cell_length_c 10.2348(6) _cell_measurement_reflns_used 11360 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 28.46 _cell_measurement_theta_min 2.39 _cell_volume 1565.11(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 0.980 _diffrn_measured_fraction_theta_max 0.935 _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 0.1146 _diffrn_reflns_av_unetI/netI 0.0817 _diffrn_reflns_Laue_measured_fraction_full 0.980 _diffrn_reflns_Laue_measured_fraction_max 0.935 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 9229 _diffrn_reflns_point_group_measured_fraction_full 0.980 _diffrn_reflns_point_group_measured_fraction_max 0.935 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.419 _diffrn_reflns_theta_min 2.384 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 1.544 _exptl_absorpt_correction_type none _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 764 _exptl_crystal_size_max 0.155 _exptl_crystal_size_mid 0.102 _exptl_crystal_size_min 0.067 _refine_diff_density_max 1.351 _refine_diff_density_min -1.284 _refine_diff_density_rms 0.146 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 3689 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0659 _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^)+(0.1356P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1957 _refine_ls_wR_factor_ref 0.2042 _reflns_number_gt 3020 _reflns_number_total 3689 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce02007d2.cif _cod_data_source_block cl096 _cod_database_code 7229977 _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 9.8474 15.5449 10.2348 90.000 92.590 90.000 ZERR 4.00 0.0005 0.0006 0.0006 0.000 0.004 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O S CU UNIT 56 68 12 12 4 4 MERG 2 FMAP 2 PLAN 10 ACTA BOND $H CONF LIST 4 L.S. 20 TEMP -140.00 WGHT 0.135600 FVAR 0.44382 C1 1 -0.067848 0.239097 0.869363 11.00000 0.04088 0.02393 = 0.03416 0.00379 0.00924 0.00614 AFIX 43 H1 2 -0.155074 0.228291 0.829275 11.00000 -1.20000 AFIX 0 C2 1 -0.033812 0.322040 0.905153 11.00000 0.06382 0.02170 = 0.03567 0.00270 0.01542 0.00985 AFIX 43 H2 2 -0.095788 0.368069 0.889049 11.00000 -1.20000 AFIX 0 C3 1 0.094243 0.336848 0.965795 11.00000 0.06122 0.02014 = 0.03101 -0.00255 0.01169 -0.00353 AFIX 43 H3 2 0.120589 0.393494 0.990865 11.00000 -1.20000 AFIX 0 C4 1 0.182157 0.268821 0.989055 11.00000 0.05130 0.02242 = 0.02978 -0.00608 0.00775 -0.00490 AFIX 43 H4 2 0.268843 0.277726 1.031432 11.00000 -1.20000 AFIX 0 C5 1 0.140917 0.186579 0.948934 11.00000 0.04104 0.02180 = 0.02237 -0.00264 0.00653 -0.00287 C6 1 0.231665 0.109181 0.966460 11.00000 0.04006 0.02195 = 0.03187 -0.00582 -0.00360 -0.00286 AFIX 23 H6A 2 0.318838 0.119822 0.924699 11.00000 -1.20000 H6B 2 0.251480 0.098770 1.060830 11.00000 -1.20000 AFIX 0 C7 1 0.235796 -0.037617 0.908338 11.00000 0.03025 0.02027 = 0.02073 -0.00083 -0.00068 -0.00179 AFIX 43 H7 2 0.324561 -0.035409 0.948602 11.00000 -1.20000 AFIX 0 C8 1 0.192085 -0.118713 0.854395 11.00000 0.03288 0.01857 = 0.01929 0.00187 -0.00025 -0.00070 C9 1 0.061156 -0.128600 0.792551 11.00000 0.03947 0.01586 = 0.02302 0.00144 0.00198 0.00006 C10 1 0.012578 -0.211735 0.731955 11.00000 0.04021 0.02398 = 0.03778 -0.00333 -0.00162 -0.00318 AFIX 133 H10A 2 -0.083096 -0.206071 0.702536 11.00000 -1.50000 H10B 2 0.021904 -0.257994 0.796793 11.00000 -1.50000 H10C 2 0.067237 -0.225372 0.657005 11.00000 -1.50000 AFIX 0 C11 1 0.287659 -0.190168 0.868256 11.00000 0.04203 0.01741 = 0.01831 0.00292 -0.00058 0.00066 C12 1 0.427212 -0.174609 0.930154 11.00000 0.03800 0.03095 = 0.03102 -0.00237 -0.00226 0.00826 AFIX 133 H12A 2 0.419472 -0.160746 1.022929 11.00000 -1.50000 H12B 2 0.470198 -0.126492 0.885976 11.00000 -1.50000 H12C 2 0.482744 -0.226469 0.921822 11.00000 -1.50000 AFIX 0 C13 1 -0.318711 0.054314 0.764173 11.00000 0.03973 0.01650 = 0.02521 0.00075 0.00014 0.00191 C22 1 0.162333 0.036347 0.553802 11.00000 0.04806 0.03089 = 0.02921 -0.00292 0.00463 -0.00518 AFIX 133 H22A 2 0.252008 0.031867 0.598845 11.00000 -1.50000 H22B 2 0.172548 0.057940 0.464824 11.00000 -1.50000 H22C 2 0.119359 -0.020514 0.549901 11.00000 -1.50000 AFIX 0 N1 3 0.018978 0.172688 0.889519 11.00000 0.03802 0.02110 = 0.02372 0.00052 0.00874 0.00159 N2 3 0.165014 0.033505 0.907309 11.00000 0.03785 0.02073 = 0.02389 -0.00218 0.00019 -0.00310 N13 3 -0.202185 0.068438 0.774598 11.00000 0.03904 0.02936 = 0.03503 0.00038 -0.00031 -0.00301 O1 4 -0.025743 -0.068385 0.780869 11.00000 0.03466 0.02110 = 0.03117 -0.00214 -0.00286 -0.00323 O2 4 0.258911 -0.264351 0.831330 11.00000 0.05111 0.01969 = 0.03781 -0.00213 -0.00009 0.00403 O21 4 0.079528 0.094172 0.623395 11.00000 0.04227 0.02249 = 0.03018 -0.00151 0.00269 -0.00540 AFIX 147 H21 2 0.123304 0.139464 0.640575 11.00000 -1.20000 AFIX 0 S13 5 -0.481652 0.036814 0.749463 11.00000 0.03645 0.03021 = 0.03593 -0.00230 0.00130 -0.00431 CU1 6 -0.010683 0.052699 0.823398 11.00000 0.03288 0.01880 = 0.02690 -0.00056 -0.00042 0.00075 HKLF 4 REM SIR97 run in space group P 21/n REM R1 = 0.0659 for 3020 Fo > 4sig(Fo) and 0.0746 for all 3689 data REM 200 parameters refined using 0 restraints END WGHT 0.1356 0.0000 REM Highest difference peak 1.351, deepest hole -1.284, 1-sigma level 0.146 Q1 1 0.0786 0.0533 0.8010 11.00000 0.05 1.35 Q2 1 -0.1004 0.0506 0.8451 11.00000 0.05 1.34 Q3 1 -0.0269 0.0524 0.9574 11.00000 0.05 0.83 Q4 1 0.0120 0.0462 0.6906 11.00000 0.05 0.77 Q5 1 -0.3947 0.0345 0.7282 11.00000 0.05 0.77 Q6 1 0.0421 0.1132 0.7618 11.00000 0.05 0.64 Q7 1 0.1021 0.0977 0.8116 11.00000 0.05 0.60 Q8 1 0.0870 0.0176 0.9208 11.00000 0.05 0.55 Q9 1 0.1807 0.0442 0.7790 11.00000 0.05 0.55 Q10 1 0.3186 0.0814 1.0395 11.00000 0.05 0.55 ; _shelx_res_checksum 46020 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 C1 C -0.0678(4) 0.2391(2) 0.8694(4) 0.0328(8) Uani 1 1 d . . H1 H -0.1551 0.2283 0.8293 0.039 Uiso 1 1 calc R U C2 C -0.0338(5) 0.3220(3) 0.9052(4) 0.0400(10) Uani 1 1 d . . H2 H -0.0958 0.3681 0.8890 0.048 Uiso 1 1 calc R U C3 C 0.0942(5) 0.3368(2) 0.9658(4) 0.0372(9) Uani 1 1 d . . H3 H 0.1206 0.3935 0.9909 0.045 Uiso 1 1 calc R U C4 C 0.1822(5) 0.2688(2) 0.9891(4) 0.0343(8) Uani 1 1 d . . H4 H 0.2688 0.2777 1.0314 0.041 Uiso 1 1 calc R U C5 C 0.1409(4) 0.1866(2) 0.9489(3) 0.0282(7) Uani 1 1 d . . C6 C 0.2317(4) 0.1092(2) 0.9665(4) 0.0314(8) Uani 1 1 d . . H6A H 0.3188 0.1198 0.9247 0.038 Uiso 1 1 calc R U H6B H 0.2515 0.0988 1.0608 0.038 Uiso 1 1 calc R U C7 C 0.2358(4) -0.0376(2) 0.9083(3) 0.0238(7) Uani 1 1 d . . H7 H 0.3246 -0.0354 0.9486 0.029 Uiso 1 1 calc R U C8 C 0.1921(4) -0.1187(2) 0.8544(3) 0.0236(7) Uani 1 1 d . . C9 C 0.0612(4) -0.1286(2) 0.7926(3) 0.0261(7) Uani 1 1 d . . C10 C 0.0126(4) -0.2117(2) 0.7320(4) 0.0341(8) Uani 1 1 d . . H10A H -0.0831 -0.2061 0.7025 0.051 Uiso 1 1 calc R U H10B H 0.0219 -0.2580 0.7968 0.051 Uiso 1 1 calc R U H10C H 0.0672 -0.2254 0.6570 0.051 Uiso 1 1 calc R U C11 C 0.2877(4) -0.1902(2) 0.8683(3) 0.0260(7) Uani 1 1 d . . C12 C 0.4272(4) -0.1746(3) 0.9302(4) 0.0334(8) Uani 1 1 d . . H12A H 0.4195 -0.1607 1.0229 0.050 Uiso 1 1 calc R U H12B H 0.4702 -0.1265 0.8860 0.050 Uiso 1 1 calc R U H12C H 0.4827 -0.2265 0.9218 0.050 Uiso 1 1 calc R U C13 C -0.3187(4) 0.0543(2) 0.7642(4) 0.0272(7) Uani 1 1 d . . C22 C 0.1623(5) 0.0363(3) 0.5538(4) 0.0360(9) Uani 1 1 d . . H22A H 0.2520 0.0319 0.5988 0.054 Uiso 1 1 calc R U H22B H 0.1725 0.0579 0.4648 0.054 Uiso 1 1 calc R U H22C H 0.1194 -0.0205 0.5499 0.054 Uiso 1 1 calc R U N1 N 0.0190(3) 0.17269(19) 0.8895(3) 0.0274(6) Uani 1 1 d . . N2 N 0.1650(3) 0.0335(2) 0.9073(3) 0.0275(6) Uani 1 1 d . . N13 N -0.2022(4) 0.0684(2) 0.7746(4) 0.0345(7) Uani 1 1 d . . O1 O -0.0257(3) -0.06839(17) 0.7809(3) 0.0291(5) Uani 1 1 d . . O2 O 0.2589(3) -0.26435(17) 0.8313(3) 0.0363(6) Uani 1 1 d . . O21 O 0.0795(3) 0.09417(17) 0.6234(3) 0.0316(6) Uani 1 1 d . . H21 H 0.1233 0.1395 0.6406 0.038 Uiso 1 1 calc R U S13 S -0.48165(11) 0.03681(7) 0.74946(10) 0.0342(3) Uani 1 1 d . . Cu1 Cu -0.01068(5) 0.05270(3) 0.82340(4) 0.0262(2) 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 0.041(2) 0.0239(18) 0.0342(19) 0.0038(14) 0.0092(15) 0.0061(15) C2 0.064(3) 0.0217(18) 0.036(2) 0.0027(15) 0.0154(19) 0.0098(18) C3 0.061(3) 0.0201(17) 0.0310(19) -0.0026(14) 0.0117(17) -0.0035(17) C4 0.051(2) 0.0224(18) 0.0298(18) -0.0061(14) 0.0077(16) -0.0049(16) C5 0.041(2) 0.0218(16) 0.0224(16) -0.0026(13) 0.0065(13) -0.0029(14) C6 0.040(2) 0.0219(17) 0.0319(18) -0.0058(14) -0.0036(15) -0.0029(15) C7 0.0303(17) 0.0203(15) 0.0207(15) -0.0008(12) -0.0007(12) -0.0018(13) C8 0.0329(18) 0.0186(15) 0.0193(14) 0.0019(12) -0.0002(12) -0.0007(13) C9 0.0395(19) 0.0159(15) 0.0230(15) 0.0014(12) 0.0020(13) 0.0001(13) C10 0.040(2) 0.0240(18) 0.038(2) -0.0033(15) -0.0016(15) -0.0032(15) C11 0.042(2) 0.0174(15) 0.0183(14) 0.0029(12) -0.0006(13) 0.0007(14) C12 0.038(2) 0.0309(19) 0.0310(18) -0.0024(15) -0.0023(15) 0.0083(16) C13 0.040(2) 0.0165(16) 0.0252(17) 0.0007(11) 0.0001(14) 0.0019(13) C22 0.048(2) 0.0309(19) 0.0292(19) -0.0029(15) 0.0046(17) -0.0052(17) N1 0.0380(17) 0.0211(14) 0.0237(14) 0.0005(11) 0.0087(12) 0.0016(12) N2 0.0379(17) 0.0207(14) 0.0239(14) -0.0022(11) 0.0002(12) -0.0031(12) N13 0.0390(19) 0.0294(16) 0.0350(17) 0.0004(14) -0.0003(14) -0.0030(15) O1 0.0347(14) 0.0211(12) 0.0312(13) -0.0021(11) -0.0029(10) -0.0032(10) O2 0.0511(18) 0.0197(13) 0.0378(15) -0.0021(11) -0.0001(12) 0.0040(12) O21 0.0423(15) 0.0225(13) 0.0302(13) -0.0015(10) 0.0027(11) -0.0054(11) S13 0.0364(6) 0.0302(5) 0.0359(5) -0.0023(4) 0.0013(4) -0.0043(4) Cu1 0.0329(3) 0.0188(3) 0.0269(3) -0.00056(14) -0.00042(19) 0.00075(15) 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' S S 0.1246 0.1234 '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 N1 C1 C2 122.0(4) N1 C1 H1 119.0 C2 C1 H1 119.0 C1 C2 C3 118.4(4) C1 C2 H2 120.8 C3 C2 H2 120.8 C4 C3 C2 119.7(4) C4 C3 H3 120.1 C2 C3 H3 120.1 C3 C4 C5 118.6(4) C3 C4 H4 120.7 C5 C4 H4 120.7 N1 C5 C4 121.6(4) N1 C5 C6 116.2(3) C4 C5 C6 122.2(4) N2 C6 C5 109.9(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 126.1(3) N2 C7 H7 116.9 C8 C7 H7 116.9 C9 C8 C7 121.2(3) C9 C8 C11 122.0(3) C7 C8 C11 116.8(3) O1 C9 C8 123.8(3) O1 C9 C10 113.2(3) C8 C9 C10 122.9(3) 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 C8 122.7(3) O2 C11 C12 117.9(3) C8 C11 C12 119.4(3) C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 N13 C13 S13 178.8(3) O21 C22 H22A 109.5 O21 C22 H22B 109.5 H22A C22 H22B 109.5 O21 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 C5 N1 C1 119.7(3) C5 N1 Cu1 114.7(2) C1 N1 Cu1 125.4(3) C7 N2 C6 116.6(3) C7 N2 Cu1 127.2(3) C6 N2 Cu1 116.0(3) C13 N13 Cu1 159.5(3) C9 O1 Cu1 130.6(2) C22 O21 Cu1 120.5(2) C22 O21 H21 109.5 Cu1 O21 H21 104.9 N2 Cu1 O1 90.45(13) N2 Cu1 N13 168.09(14) O1 Cu1 N13 90.06(13) N2 Cu1 N1 83.04(14) O1 Cu1 N1 172.19(12) N13 Cu1 N1 95.43(14) N2 Cu1 O21 93.65(12) O1 Cu1 O21 95.66(10) N13 Cu1 O21 98.14(13) N1 Cu1 O21 89.07(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.350(5) C1 C2 1.378(6) C1 H1 0.9500 C2 C3 1.399(7) C2 H2 0.9500 C3 C4 1.381(6) C3 H3 0.9500 C4 C5 1.397(5) C4 H4 0.9500 C5 N1 1.339(5) C5 C6 1.505(5) C6 N2 1.465(5) C6 H6A 0.9900 C6 H6B 0.9900 C7 N2 1.307(5) C7 C8 1.434(5) C7 H7 0.9500 C8 C9 1.419(5) C8 C11 1.459(5) C9 O1 1.270(4) C9 C10 1.502(5) C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 C11 O2 1.242(4) C11 C12 1.507(5) C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 N13 1.168(6) C13 S13 1.628(4) C22 O21 1.426(5) C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 N1 Cu1 2.001(3) N2 Cu1 1.920(3) N13 Cu1 1.944(4) O1 Cu1 1.936(3) O21 Cu1 2.358(3) O21 H21 0.8400 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 -0.9(6) C1 C2 C3 C4 -0.5(6) C2 C3 C4 C5 1.0(6) C3 C4 C5 N1 -0.3(5) C3 C4 C5 C6 178.1(3) N1 C5 C6 N2 2.3(5) C4 C5 C6 N2 -176.1(3) N2 C7 C8 C9 -0.2(5) N2 C7 C8 C11 -179.2(3) C7 C8 C9 O1 -0.4(5) C11 C8 C9 O1 178.6(3) C7 C8 C9 C10 178.5(3) C11 C8 C9 C10 -2.5(5) C9 C8 C11 O2 -2.7(5) C7 C8 C11 O2 176.4(3) C9 C8 C11 C12 177.6(3) C7 C8 C11 C12 -3.4(5) C4 C5 N1 C1 -1.1(5) C6 C5 N1 C1 -179.5(3) C4 C5 N1 Cu1 173.7(3) C6 C5 N1 Cu1 -4.7(4) C2 C1 N1 C5 1.7(5) C2 C1 N1 Cu1 -172.5(3) C8 C7 N2 C6 -178.9(3) C8 C7 N2 Cu1 -4.9(5) C5 C6 N2 C7 176.0(3) C5 C6 N2 Cu1 1.3(4) C8 C9 O1 Cu1 6.2(5) C10 C9 O1 Cu1 -172.8(2)