#------------------------------------------------------------------------------ #$Date: 2019-11-17 09:06:29 +0200 (Sun, 17 Nov 2019) $ #$Revision: 229011 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229974.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_7229974 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 'C13 H15 Cu N5 O3' _chemical_formula_sum 'C13 H15 Cu N5 O3' _chemical_formula_weight 352.84 _chemical_name_common '[CuL30aN3]' _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 2017-08-03 _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 94.083(4) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 20.5772(11) _cell_length_b 19.5249(15) _cell_length_c 7.1596(4) _cell_measurement_reflns_used 7370 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 28.36 _cell_measurement_theta_min 1.99 _cell_volume 2869.2(3) _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 0.943 _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 0.0335 _diffrn_reflns_av_unetI/netI 0.0432 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.943 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 9743 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.943 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.441 _diffrn_reflns_theta_min 1.439 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 1.543 _exptl_absorpt_correction_type none _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1448 _exptl_crystal_size_max 0.145 _exptl_crystal_size_mid 0.071 _exptl_crystal_size_min 0.068 _refine_diff_density_max 0.316 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 3420 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.937 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0271 _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^)+(0.0282P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.0609 _reflns_number_gt 2680 _reflns_number_total 3420 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce02007d2.cif _cod_data_source_block cl098 _cod_depositor_comments ; 2018-03-04 Z value and formula fixed to values more according to usual chemical conventions. miguel Adding full bibliography for 7229962--7229987.cif. ; _cod_original_formula_moiety 'C26 H30 Cu2 N10 O6' _cod_original_formula_sum 'C26 H30 Cu2 N10 O6' _cod_original_formula_units_Z 4 _cod_original_formula_weight 705.68 _cod_database_code 7229974 _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 20.5772 19.5249 7.1596 90.000 94.083 90.000 ZERR 4.00 0.0011 0.0015 0.0004 0.000 0.004 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H N O CU UNIT 104 120 40 24 8 MERG 2 FMAP 2 PLAN 10 ACTA BOND $H CONF LIST 4 OMIT 0 2 0 L.S. 20 TEMP -140.00 WGHT 0.028200 FVAR 0.12416 C1 1 0.373874 0.162535 0.139396 11.00000 0.01842 0.02134 = 0.02064 0.00100 0.00376 -0.00103 AFIX 43 H1 2 0.386119 0.206362 0.096202 11.00000 -1.20000 AFIX 0 C2 1 0.416477 0.108031 0.127394 11.00000 0.01675 0.02495 = 0.02279 -0.00046 0.00515 0.00211 AFIX 43 H2 2 0.457885 0.114377 0.079164 11.00000 -1.20000 AFIX 0 C3 1 0.397478 0.044156 0.187102 11.00000 0.01960 0.02139 = 0.02499 -0.00160 0.00215 0.00412 AFIX 43 H3 2 0.425583 0.005898 0.177715 11.00000 -1.20000 AFIX 0 C4 1 0.337369 0.035986 0.260692 11.00000 0.01920 0.01768 = 0.02420 -0.00001 0.00249 0.00180 AFIX 43 H4 2 0.323776 -0.007562 0.302450 11.00000 -1.20000 AFIX 0 C5 1 0.297567 0.093124 0.271747 11.00000 0.01649 0.01873 = 0.01819 0.00126 0.00236 0.00067 C6 1 0.232947 0.088915 0.356694 11.00000 0.01951 0.01899 = 0.03143 0.00582 0.00948 0.00236 AFIX 23 H6A 2 0.204964 0.054525 0.288603 11.00000 -1.20000 H6B 2 0.239558 0.074378 0.489156 11.00000 -1.20000 AFIX 0 C7 1 0.143749 0.161972 0.410344 11.00000 0.01923 0.02056 = 0.01721 0.00297 0.00151 0.00076 AFIX 43 H7 2 0.125271 0.121850 0.459749 11.00000 -1.20000 AFIX 0 C8 1 0.106253 0.223618 0.413286 11.00000 0.01668 0.02145 = 0.01658 0.00060 0.00298 0.00197 C9 1 0.130644 0.287344 0.359050 11.00000 0.01746 0.02225 = 0.01668 -0.00356 0.00082 0.00243 C10 1 0.092908 0.352990 0.362137 11.00000 0.02035 0.02213 = 0.02701 -0.00252 0.00369 0.00436 AFIX 133 H10A 2 0.120161 0.390859 0.323363 11.00000 -1.50000 H10B 2 0.080012 0.361501 0.489231 11.00000 -1.50000 H10C 2 0.053889 0.349512 0.275834 11.00000 -1.50000 AFIX 0 C11 1 0.038686 0.218319 0.468117 11.00000 0.01796 0.02847 = 0.01691 0.00022 0.00383 0.00319 C12 1 -0.048130 0.142873 0.525651 11.00000 0.01492 0.03733 = 0.03172 0.00711 0.00796 0.00195 AFIX 23 H12A 2 -0.077457 0.171772 0.443224 11.00000 -1.20000 H12B 2 -0.053547 0.155685 0.657427 11.00000 -1.20000 AFIX 0 C13 1 -0.063825 0.068279 0.494537 11.00000 0.02694 0.03618 = 0.11490 0.01428 0.02686 -0.00068 AFIX 133 H13A 2 -0.055227 0.055535 0.366218 11.00000 -1.50000 H13B 2 -0.109869 0.060246 0.513968 11.00000 -1.50000 H13C 2 -0.036599 0.040484 0.583163 11.00000 -1.50000 AFIX 0 N1 3 0.315359 0.154848 0.211027 11.00000 0.01568 0.01770 = 0.01874 0.00194 0.00267 0.00166 N2 3 0.201001 0.156210 0.345744 11.00000 0.01717 0.01712 = 0.02105 0.00178 0.00297 0.00275 N3 3 0.299393 0.298658 0.108031 11.00000 0.01951 0.01685 = 0.02806 0.00100 0.00679 0.00175 N4 3 0.288891 0.358167 0.137188 11.00000 0.01749 0.02226 = 0.02304 0.00193 0.00488 -0.00175 N5 3 0.279907 0.415778 0.159033 11.00000 0.03690 0.01867 = 0.04388 -0.00128 0.01236 0.00052 O1 4 0.187248 0.295141 0.298978 11.00000 0.01911 0.01880 = 0.03173 -0.00016 0.00802 0.00131 O2 4 0.002365 0.265512 0.495116 11.00000 0.02229 0.02971 = 0.04027 -0.00082 0.01118 0.00405 O3 4 0.019125 0.152324 0.481676 11.00000 0.01560 0.02754 = 0.03361 0.00433 0.00822 0.00168 CU1 5 0.248570 0.227872 0.230113 11.00000 0.01537 0.01572 = 0.02211 0.00191 0.00521 0.00163 HKLF 4 REM SIR97 run in space group C 2/c REM R1 = 0.0271 for 2680 Fo > 4sig(Fo) and 0.0407 for all 3420 data REM 199 parameters refined using 0 restraints END WGHT 0.0282 0.0000 REM Highest difference peak 0.316, deepest hole -0.285, 1-sigma level 0.063 Q1 1 0.3201 0.0665 0.2817 11.00000 0.05 0.32 Q2 1 0.2506 0.2297 0.3639 11.00000 0.05 0.31 Q3 1 0.1305 0.1965 0.4361 11.00000 0.05 0.29 Q4 1 0.2813 0.2851 0.0185 11.00000 0.05 0.29 Q5 1 0.3925 0.1283 0.1220 11.00000 0.05 0.27 Q6 1 0.2700 0.0877 0.3061 11.00000 0.05 0.27 Q7 1 0.2227 0.1844 0.3095 11.00000 0.05 0.27 Q8 1 0.2680 0.2730 0.1472 11.00000 0.05 0.26 Q9 1 0.1186 0.2531 0.3870 11.00000 0.05 0.26 Q10 1 0.2485 0.2308 0.0867 11.00000 0.05 0.25 ; _shelx_res_checksum 97497 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 C1 C 0.37387(8) 0.16253(10) 0.1394(2) 0.0200(4) Uani 1 1 d . . H1 H 0.3861 0.2064 0.0962 0.024 Uiso 1 1 calc R U C2 C 0.41648(9) 0.10803(10) 0.1274(2) 0.0213(4) Uani 1 1 d . . H2 H 0.4579 0.1144 0.0792 0.026 Uiso 1 1 calc R U C3 C 0.39748(9) 0.04416(10) 0.1871(2) 0.0220(4) Uani 1 1 d . . H3 H 0.4256 0.0059 0.1777 0.026 Uiso 1 1 calc R U C4 C 0.33737(9) 0.03599(10) 0.2607(2) 0.0203(4) Uani 1 1 d . . H4 H 0.3238 -0.0076 0.3025 0.024 Uiso 1 1 calc R U C5 C 0.29757(8) 0.09312(10) 0.2717(2) 0.0177(3) Uani 1 1 d . . C6 C 0.23295(9) 0.08891(10) 0.3567(3) 0.0229(4) Uani 1 1 d . . H6A H 0.2050 0.0545 0.2886 0.028 Uiso 1 1 calc R U H6B H 0.2396 0.0744 0.4892 0.028 Uiso 1 1 calc R U C7 C 0.14375(8) 0.16197(10) 0.4103(2) 0.0190(4) Uani 1 1 d . . H7 H 0.1253 0.1219 0.4597 0.023 Uiso 1 1 calc R U C8 C 0.10625(8) 0.22362(10) 0.4133(2) 0.0181(3) Uani 1 1 d . . C9 C 0.13064(8) 0.28734(10) 0.3591(2) 0.0188(4) Uani 1 1 d . . C10 C 0.09291(9) 0.35299(10) 0.3621(3) 0.0231(4) Uani 1 1 d . . H10A H 0.1202 0.3909 0.3234 0.035 Uiso 1 1 calc R U H10B H 0.0800 0.3615 0.4892 0.035 Uiso 1 1 calc R U H10C H 0.0539 0.3495 0.2758 0.035 Uiso 1 1 calc R U C11 C 0.03869(8) 0.21832(10) 0.4681(2) 0.0210(4) Uani 1 1 d . . C12 C -0.04813(9) 0.14287(12) 0.5257(3) 0.0277(4) Uani 1 1 d . . H12A H -0.0775 0.1718 0.4432 0.033 Uiso 1 1 calc R U H12B H -0.0535 0.1557 0.6574 0.033 Uiso 1 1 calc R U C13 C -0.06382(12) 0.06828(14) 0.4945(5) 0.0583(8) Uani 1 1 d . . H13A H -0.0552 0.0555 0.3662 0.087 Uiso 1 1 calc R U H13B H -0.1099 0.0602 0.5140 0.087 Uiso 1 1 calc R U H13C H -0.0366 0.0405 0.5832 0.087 Uiso 1 1 calc R U N1 N 0.31536(7) 0.15485(8) 0.21103(19) 0.0173(3) Uani 1 1 d . . N2 N 0.20100(7) 0.15621(8) 0.3457(2) 0.0184(3) Uani 1 1 d . . N3 N 0.29939(7) 0.29866(8) 0.1080(2) 0.0212(3) Uani 1 1 d . . N4 N 0.28889(7) 0.35817(9) 0.1372(2) 0.0208(3) Uani 1 1 d . . N5 N 0.27991(9) 0.41578(9) 0.1590(3) 0.0327(4) Uani 1 1 d . . O1 O 0.18725(6) 0.29514(7) 0.29898(18) 0.0229(3) Uani 1 1 d . . O2 O 0.00236(6) 0.26551(8) 0.49512(19) 0.0303(3) Uani 1 1 d . . O3 O 0.01912(6) 0.15232(8) 0.48168(19) 0.0253(3) Uani 1 1 d . . Cu1 Cu 0.24857(2) 0.22787(2) 0.23011(3) 0.01755(7) 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 0.0184(8) 0.0213(10) 0.0206(8) 0.0010(7) 0.0038(7) -0.0010(7) C2 0.0168(8) 0.0249(10) 0.0228(8) -0.0005(8) 0.0052(7) 0.0021(7) C3 0.0196(9) 0.0214(10) 0.0250(8) -0.0016(8) 0.0022(7) 0.0041(7) C4 0.0192(8) 0.0177(10) 0.0242(8) 0.0000(7) 0.0025(7) 0.0018(7) C5 0.0165(8) 0.0187(9) 0.0182(7) 0.0013(7) 0.0024(7) 0.0007(6) C6 0.0195(9) 0.0190(10) 0.0314(9) 0.0058(8) 0.0095(8) 0.0024(7) C7 0.0192(8) 0.0206(10) 0.0172(7) 0.0030(7) 0.0015(7) 0.0008(7) C8 0.0167(7) 0.0215(9) 0.0166(7) 0.0006(7) 0.0030(6) 0.0020(7) C9 0.0175(8) 0.0222(10) 0.0167(7) -0.0036(7) 0.0008(6) 0.0024(7) C10 0.0203(8) 0.0221(10) 0.0270(9) -0.0025(8) 0.0037(7) 0.0044(7) C11 0.0180(8) 0.0285(11) 0.0169(7) 0.0002(8) 0.0038(6) 0.0032(7) C12 0.0149(9) 0.0373(13) 0.0317(10) 0.0071(9) 0.0080(8) 0.0020(8) C13 0.0269(11) 0.0362(15) 0.115(2) 0.0143(16) 0.0269(14) -0.0007(11) N1 0.0157(7) 0.0177(8) 0.0187(6) 0.0019(6) 0.0027(6) 0.0017(6) N2 0.0172(7) 0.0171(8) 0.0210(7) 0.0018(6) 0.0030(6) 0.0027(6) N3 0.0195(7) 0.0169(8) 0.0281(7) 0.0010(6) 0.0068(6) 0.0018(6) N4 0.0175(7) 0.0223(9) 0.0230(7) 0.0019(6) 0.0049(6) -0.0017(6) N5 0.0369(10) 0.0187(10) 0.0439(10) -0.0013(8) 0.0124(8) 0.0005(7) O1 0.0191(6) 0.0188(7) 0.0317(7) -0.0002(5) 0.0080(5) 0.0013(5) O2 0.0223(6) 0.0297(9) 0.0403(8) -0.0008(7) 0.0112(6) 0.0040(6) O3 0.0156(6) 0.0275(8) 0.0336(7) 0.0043(6) 0.0082(5) 0.0017(5) Cu1 0.01537(10) 0.01572(11) 0.02211(10) 0.00191(9) 0.00521(8) 0.00163(9) 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 N1 C1 C2 121.57(18) N1 C1 H1 119.2 C2 C1 H1 119.2 C3 C2 C1 118.64(17) C3 C2 H2 120.7 C1 C2 H2 120.7 C2 C3 C4 120.00(18) C2 C3 H3 120.0 C4 C3 H3 120.0 C3 C4 C5 118.31(18) C3 C4 H4 120.8 C5 C4 H4 120.8 N1 C5 C4 121.83(16) N1 C5 C6 116.75(16) C4 C5 C6 121.40(17) N2 C6 C5 109.57(15) N2 C6 H6A 109.8 C5 C6 H6A 109.8 N2 C6 H6B 109.8 C5 C6 H6B 109.8 H6A C6 H6B 108.2 N2 C7 C8 125.52(18) N2 C7 H7 117.2 C8 C7 H7 117.2 C9 C8 C7 122.46(16) C9 C8 C11 119.81(16) C7 C8 C11 117.68(17) O1 C9 C8 123.33(16) O1 C9 C10 112.84(16) C8 C9 C10 123.83(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 121.48(16) O2 C11 C8 126.40(19) O3 C11 C8 112.09(16) O3 C12 C13 106.77(17) O3 C12 H12A 110.4 C13 C12 H12A 110.4 O3 C12 H12B 110.4 C13 C12 H12B 110.4 H12A C12 H12B 108.6 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 119.63(16) C5 N1 Cu1 114.55(12) C1 N1 Cu1 125.79(13) C7 N2 C6 118.14(16) C7 N2 Cu1 126.18(14) C6 N2 Cu1 115.67(11) N4 N3 Cu1 119.47(12) N5 N4 N3 177.4(2) C9 O1 Cu1 129.72(12) C11 O3 C12 115.38(15) O1 Cu1 N2 91.33(6) O1 Cu1 N3 90.77(6) N2 Cu1 N3 177.88(7) O1 Cu1 N1 168.99(6) N2 Cu1 N1 83.33(6) N3 Cu1 N1 94.64(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.350(2) C1 C2 1.385(3) C1 H1 0.9500 C2 C3 1.384(3) C2 H2 0.9500 C3 C4 1.388(2) C3 H3 0.9500 C4 C5 1.390(3) C4 H4 0.9500 C5 N1 1.341(2) C5 C6 1.503(2) C6 N2 1.469(2) C6 H6A 0.9900 C6 H6B 0.9900 C7 N2 1.301(2) C7 C8 1.431(3) C7 H7 0.9500 C8 C9 1.407(3) C8 C11 1.475(2) C9 O1 1.279(2) C9 C10 1.500(3) C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 C11 O2 1.211(2) C11 O3 1.355(2) C12 O3 1.453(2) C12 C13 1.505(3) C12 H12A 0.9900 C12 H12B 0.9900 C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 N1 Cu1 1.9917(15) N2 Cu1 1.9278(16) N3 N4 1.203(2) N3 Cu1 1.9743(16) N4 N5 1.152(2) O1 Cu1 1.9102(13) 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 1.4(3) C1 C2 C3 C4 -1.3(3) C2 C3 C4 C5 0.1(3) C3 C4 C5 N1 1.0(3) C3 C4 C5 C6 -177.56(16) N1 C5 C6 N2 2.6(2) C4 C5 C6 N2 -178.71(16) N2 C7 C8 C9 -5.6(3) N2 C7 C8 C11 171.81(16) C7 C8 C9 O1 1.7(3) C11 C8 C9 O1 -175.62(15) C7 C8 C9 C10 -179.41(15) C11 C8 C9 C10 3.3(2) C9 C8 C11 O2 -10.0(3) C7 C8 C11 O2 172.56(17) C9 C8 C11 O3 168.31(14) C7 C8 C11 O3 -9.1(2) C4 C5 N1 C1 -1.0(2) C6 C5 N1 C1 177.66(15) C4 C5 N1 Cu1 177.20(13) C6 C5 N1 Cu1 -4.2(2) C2 C1 N1 C5 -0.2(3) C2 C1 N1 Cu1 -178.20(13) C8 C7 N2 C6 179.05(16) C8 C7 N2 Cu1 -2.3(3) C5 C6 N2 C7 178.94(15) C5 C6 N2 Cu1 0.16(19) C8 C9 O1 Cu1 10.1(2) C10 C9 O1 Cu1 -168.95(11) O2 C11 O3 C12 1.5(2) C8 C11 O3 C12 -176.92(14) C13 C12 O3 C11 168.39(19)