#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:30:42 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270477 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060966.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_7060966 loop_ _publ_author_name 'Wu, Jialu' 'Li, Bo' 'Wang, Hong' 'Lai, Yingzhen' 'Ye, Yue' 'Zou, Yongkang' 'Tian, Jumei' 'Xu, Yaohua' _publ_section_title ; How the magnetic field impacts the chiroptical activities of helical copper enantiomers ; _journal_issue 42 _journal_name_full 'New Journal of Chemistry' _journal_page_first 20021 _journal_page_last 20027 _journal_paper_doi 10.1039/D1NJ03803F _journal_volume 45 _journal_year 2021 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C14 H18 Cu N2 O5, 2(H2 O)' _chemical_formula_sum 'C14 H22 Cu N2 O7' _chemical_formula_weight 393.89 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014 _audit_update_record ; 2021-09-13 deposited with the CCDC. 2021-09-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.1946(11) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.39160(13) _cell_length_b 5.69116(6) _cell_length_c 12.43561(14) _cell_measurement_reflns_used 13654 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 73.2270 _cell_measurement_theta_min 3.6250 _cell_volume 788.027(15) _computing_cell_refinement 'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)' _computing_molecular_graphics 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 10 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_unetI/netI 0.0201 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 16668 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.948 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.311 _diffrn_reflns_theta_min 3.636 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 2.339 _exptl_absorpt_correction_T_max 0.791 _exptl_absorpt_correction_T_min 0.750 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 410 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.195 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.044 _refine_ls_abs_structure_details ; Flack x determined using 1289 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.010(12) _refine_ls_extinction_coef 0.0059(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 231 _refine_ls_number_reflns 3029 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0215 _refine_ls_R_factor_gt 0.0214 _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^)+(0.0287P)^2^+0.4521P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.0561 _reflns_Friedel_coverage 0.749 _reflns_Friedel_fraction_full 0.972 _reflns_Friedel_fraction_max 0.909 _reflns_number_gt 3020 _reflns_number_total 3195 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03803f2.cif _cod_data_source_block D-1 _cod_depositor_comments 'Adding full bibliography for 7060966--7060967.cif.' _cod_original_cell_volume 788.026(15) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7060966 _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_estimated_absorpt_t_min 0.455 _shelx_estimated_absorpt_t_max 0.800 _shelxl_version_number 2014-3 _shelx_res_file ; TITL exp_2119_a.res in P2(1) CELL 1.54184 11.391601 5.691157 12.435615 90 102.1946 90 ZERR 2 0.000129 0.000063 0.000139 0 0.0011 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H Cu N O UNIT 28 44 2 4 14 L.S. 5 ACTA BOND $H FMAP 2 PLAN 5 MORE -1 CONF OMIT -6 -5 9 OMIT -2 -3 14 SIZE 0.1 0.12 0.4 TEMP -123.15(10) WGHT 0.028700 0.452100 EXTI 0.005935 FVAR 9.17318 CU1 3 0.100933 0.665246 0.671557 11.00000 0.01590 0.01377 = 0.01286 -0.00014 0.00446 0.00118 C1 1 0.291767 0.391821 0.605738 11.00000 0.01502 0.02100 = 0.01956 0.00108 0.00147 0.00443 AFIX 23 H1A 2 0.287085 0.220007 0.616555 11.00000 -1.20000 H1B 2 0.327054 0.465984 0.677278 11.00000 -1.20000 AFIX 0 C2 1 0.366422 0.447314 0.521086 11.00000 0.01721 0.02961 = 0.02593 0.00297 0.00718 0.00859 AFIX 23 H2A 2 0.355612 0.325991 0.462770 11.00000 -1.20000 H2B 2 0.452780 0.459449 0.555909 11.00000 -1.20000 AFIX 0 C3 1 0.316381 0.683382 0.475077 11.00000 0.01500 0.02824 = 0.02754 0.00568 0.01039 0.00450 AFIX 23 H3A 2 0.334421 0.712863 0.401790 11.00000 -1.20000 H3B 2 0.349429 0.813577 0.525198 11.00000 -1.20000 AFIX 0 C4 1 0.180245 0.655159 0.467269 11.00000 0.01638 0.01756 = 0.01290 -0.00017 0.00375 0.00122 AFIX 13 H4 2 0.142644 0.581672 0.395170 11.00000 -1.20000 AFIX 0 C5 1 0.119660 0.889116 0.478945 11.00000 0.00950 0.01596 = 0.01699 0.00001 0.00170 -0.00131 C6 1 0.116222 0.730735 0.899781 11.00000 0.01751 0.01670 = 0.01235 0.00074 0.00453 0.00183 AFIX 13 H6 2 0.059939 0.759156 0.950190 11.00000 -1.20000 AFIX 0 C7 1 0.117644 0.468250 0.875277 11.00000 0.01280 0.01929 = 0.01589 -0.00160 0.00338 -0.00053 C8 1 0.242488 0.810612 0.957751 11.00000 0.01968 0.01742 = 0.01551 -0.00251 0.00368 -0.00052 AFIX 23 H8A 2 0.238904 0.979858 0.975172 11.00000 -1.20000 H8B 2 0.265021 0.725156 1.028452 11.00000 -1.20000 AFIX 0 C9 1 0.341235 0.774996 0.894590 11.00000 0.01542 0.01920 = 0.01587 -0.00106 0.00103 -0.00298 C10 1 0.366025 0.946937 0.822723 11.00000 0.02212 0.01949 = 0.02054 0.00315 0.00274 0.00060 AFIX 43 H10 2 0.317697 1.084353 0.810451 11.00000 -1.20000 AFIX 0 C11 1 0.460779 0.920460 0.768455 11.00000 0.02236 0.02337 = 0.02383 0.00443 0.00576 -0.00288 AFIX 43 H11 2 0.476572 1.039101 0.719666 11.00000 -1.20000 AFIX 0 C12 1 0.531652 0.720531 0.786041 11.00000 0.01449 0.02921 = 0.01918 -0.00214 0.00267 -0.00180 C13 1 0.508404 0.547715 0.856784 11.00000 0.01796 0.02351 = 0.02189 0.00155 0.00081 0.00252 AFIX 43 H13 2 0.556630 0.410110 0.868470 11.00000 -1.20000 AFIX 0 C14 1 0.413761 0.576042 0.911048 11.00000 0.01946 0.01934 = 0.01742 0.00026 0.00186 -0.00134 AFIX 43 H14 2 0.398649 0.457291 0.960079 11.00000 -1.20000 AFIX 0 N1 4 0.169487 0.491564 0.559046 11.00000 0.01257 0.01311 = 0.01496 0.00074 0.00191 0.00120 AFIX 13 H1 2 0.113989 0.360228 0.528699 11.00000 -1.20000 AFIX 0 N2 4 0.070707 0.858233 0.795156 11.00000 0.01592 0.01677 = 0.01672 0.00106 0.00408 0.00190 AFIX 23 H2C 2 0.108734 0.999104 0.796255 11.00000 -1.20000 H2D 2 -0.009432 0.885521 0.786736 11.00000 -1.20000 AFIX 0 O1 5 0.087144 0.930070 0.569535 11.00000 0.01908 0.01601 = 0.01548 0.00014 0.00564 0.00177 O2 5 0.106117 1.034359 0.402297 11.00000 0.01924 0.02136 = 0.01904 0.00555 0.00706 0.00320 O3 5 0.117829 0.406066 0.776157 11.00000 0.02383 0.01529 = 0.01683 -0.00089 0.00630 -0.00029 O4 5 0.122745 0.326701 0.951757 11.00000 0.03306 0.01720 = 0.01877 0.00399 0.00729 0.00091 O5 5 0.623474 0.703240 0.730430 11.00000 0.02245 0.03676 = 0.02931 0.00342 0.01160 0.00334 AFIX 147 H5 2 0.661071 0.577172 0.747744 11.00000 -1.50000 AFIX 0 O6 5 0.831850 0.969046 0.833811 11.00000 0.02580 0.02901 = 0.02220 -0.00249 0.00695 -0.00184 H6A 2 0.847862 0.926908 0.905553 11.00000 -1.50000 H6B 2 0.780057 0.878128 0.799950 11.00000 -1.50000 O7 5 0.807430 0.433058 0.785475 11.00000 0.03682 0.03011 = 0.02869 0.00202 0.01863 0.00630 H7A 2 0.833900 0.452019 0.732547 11.00000 -1.50000 H7B 2 0.811103 0.301982 0.802236 11.00000 -1.50000 HKLF 4 REM exp_2119_a.res in P2(1) REM R1 = 0.0214 for 3020 Fo > 4sig(Fo) and 0.0215 for all 3029 data REM 231 parameters refined using 1 restraints END WGHT 0.0302 0.3729 REM Highest difference peak 0.195, deepest hole -0.220, 1-sigma level 0.044 Q1 1 0.1029 0.4988 0.6638 11.00000 0.05 0.19 Q2 1 0.1046 0.5842 0.8862 11.00000 0.05 0.19 Q3 1 0.1692 0.5610 0.5100 11.00000 0.05 0.19 Q4 1 0.3541 0.5779 0.4978 11.00000 0.05 0.19 Q5 1 0.0727 0.8239 0.7451 11.00000 0.05 0.19 ; _shelx_res_checksum 48226 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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 _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.10093(3) 0.66525(6) 0.67156(3) 0.01396(12) Uani 1 1 d . . . . . C1 C 0.2918(2) 0.3918(5) 0.6057(2) 0.0188(5) Uani 1 1 d . . . . . H1A H 0.2871 0.2200 0.6166 0.023 Uiso 1 1 calc R U . . . H1B H 0.3271 0.4660 0.6773 0.023 Uiso 1 1 calc R U . . . C2 C 0.3664(2) 0.4473(6) 0.5211(2) 0.0239(6) Uani 1 1 d . . . . . H2A H 0.3556 0.3260 0.4628 0.029 Uiso 1 1 calc R U . . . H2B H 0.4528 0.4594 0.5559 0.029 Uiso 1 1 calc R U . . . C3 C 0.3164(2) 0.6834(6) 0.4751(2) 0.0227(6) Uani 1 1 d . . . . . H3A H 0.3344 0.7129 0.4018 0.027 Uiso 1 1 calc R U . . . H3B H 0.3494 0.8136 0.5252 0.027 Uiso 1 1 calc R U . . . C4 C 0.18024(19) 0.6552(6) 0.46727(18) 0.0155(5) Uani 1 1 d . . . . . H4 H 0.1426 0.5817 0.3952 0.019 Uiso 1 1 calc R U . . . C5 C 0.1197(2) 0.8891(5) 0.4789(2) 0.0143(5) Uani 1 1 d . . . . . C6 C 0.1162(2) 0.7307(5) 0.8998(2) 0.0153(6) Uani 1 1 d . . . . . H6 H 0.0599 0.7592 0.9502 0.018 Uiso 1 1 calc R U . . . C7 C 0.1176(2) 0.4682(5) 0.8753(2) 0.0159(5) Uani 1 1 d . . . . . C8 C 0.2425(2) 0.8106(5) 0.9578(2) 0.0175(5) Uani 1 1 d . . . . . H8A H 0.2389 0.9799 0.9752 0.021 Uiso 1 1 calc R U . . . H8B H 0.2650 0.7252 1.0285 0.021 Uiso 1 1 calc R U . . . C9 C 0.3412(2) 0.7750(5) 0.8946(2) 0.0172(5) Uani 1 1 d . . . . . C10 C 0.3660(3) 0.9469(5) 0.8227(2) 0.0210(6) Uani 1 1 d . . . . . H10 H 0.3177 1.0844 0.8105 0.025 Uiso 1 1 calc R U . . . C11 C 0.4608(2) 0.9205(6) 0.7685(2) 0.0231(6) Uani 1 1 d . . . . . H11 H 0.4766 1.0391 0.7197 0.028 Uiso 1 1 calc R U . . . C12 C 0.5317(2) 0.7205(5) 0.7860(2) 0.0211(6) Uani 1 1 d . . . . . C13 C 0.5084(2) 0.5477(5) 0.8568(2) 0.0216(6) Uani 1 1 d . . . . . H13 H 0.5566 0.4101 0.8685 0.026 Uiso 1 1 calc R U . . . C14 C 0.4138(2) 0.5760(5) 0.9110(2) 0.0190(5) Uani 1 1 d . . . . . H14 H 0.3986 0.4573 0.9601 0.023 Uiso 1 1 calc R U . . . N1 N 0.16949(19) 0.4916(4) 0.55905(17) 0.0137(4) Uani 1 1 d . . . . . H1 H 0.1140 0.3602 0.5287 0.016 Uiso 1 1 calc R U . . . N2 N 0.0707(2) 0.8582(4) 0.79516(18) 0.0164(5) Uani 1 1 d . . . . . H2C H 0.1087 0.9991 0.7963 0.020 Uiso 1 1 calc R U . . . H2D H -0.0094 0.8855 0.7867 0.020 Uiso 1 1 calc R U . . . O1 O 0.08714(16) 0.9301(3) 0.56954(14) 0.0166(4) Uani 1 1 d . . . . . O2 O 0.10612(17) 1.0344(4) 0.40230(15) 0.0194(4) Uani 1 1 d . . . . . O3 O 0.11783(17) 0.4061(4) 0.77616(15) 0.0184(4) Uani 1 1 d . . . . . O4 O 0.12275(19) 0.3267(4) 0.95176(16) 0.0227(4) Uani 1 1 d . . . . . O5 O 0.62347(17) 0.7032(4) 0.73043(17) 0.0286(5) Uani 1 1 d . . . . . H5 H 0.6611 0.5772 0.7477 0.043 Uiso 1 1 calc R U . . . O6 O 0.8318(2) 0.9690(4) 0.83381(18) 0.0254(5) Uani 1 1 d . . . . . H6A H 0.848(3) 0.927(8) 0.906(4) 0.038 Uiso 1 1 d . U . . . H6B H 0.780(4) 0.878(9) 0.800(4) 0.038 Uiso 1 1 d . U . . . O7 O 0.8074(2) 0.4331(5) 0.7855(2) 0.0302(5) Uani 1 1 d . . . . . H7A H 0.834(4) 0.452(9) 0.733(4) 0.045 Uiso 1 1 d . U . . . H7B H 0.811(4) 0.302(9) 0.802(4) 0.045 Uiso 1 1 d . 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 0.01590(18) 0.01377(19) 0.01286(17) -0.00014(15) 0.00446(12) 0.00118(15) C1 0.0150(12) 0.0210(14) 0.0196(13) 0.0011(11) 0.0015(10) 0.0044(10) C2 0.0172(13) 0.0296(17) 0.0259(14) 0.0030(12) 0.0072(11) 0.0086(12) C3 0.0150(11) 0.0282(16) 0.0275(13) 0.0057(14) 0.0104(9) 0.0045(13) C4 0.0164(10) 0.0176(12) 0.0129(10) -0.0002(12) 0.0038(8) 0.0012(13) C5 0.0095(10) 0.0160(14) 0.0170(12) 0.0000(10) 0.0017(9) -0.0013(9) C6 0.0175(12) 0.0167(15) 0.0124(11) 0.0007(9) 0.0045(9) 0.0018(9) C7 0.0128(11) 0.0193(15) 0.0159(12) -0.0016(11) 0.0034(9) -0.0005(10) C8 0.0197(13) 0.0174(14) 0.0155(12) -0.0025(10) 0.0037(10) -0.0005(10) C9 0.0154(12) 0.0192(13) 0.0159(12) -0.0011(10) 0.0010(10) -0.0030(10) C10 0.0221(13) 0.0195(16) 0.0205(13) 0.0032(11) 0.0027(10) 0.0006(12) C11 0.0224(13) 0.0234(15) 0.0238(14) 0.0044(12) 0.0058(11) -0.0029(12) C12 0.0145(11) 0.0292(18) 0.0192(12) -0.0021(10) 0.0027(9) -0.0018(10) C13 0.0180(12) 0.0235(16) 0.0219(13) 0.0015(12) 0.0008(10) 0.0025(11) C14 0.0195(13) 0.0193(13) 0.0174(12) 0.0003(10) 0.0019(10) -0.0013(11) N1 0.0126(10) 0.0131(11) 0.0150(10) 0.0007(8) 0.0019(8) 0.0012(8) N2 0.0159(10) 0.0168(12) 0.0167(11) 0.0011(9) 0.0041(8) 0.0019(9) O1 0.0191(9) 0.0160(10) 0.0155(8) 0.0001(7) 0.0056(7) 0.0018(8) O2 0.0192(9) 0.0214(11) 0.0190(9) 0.0056(8) 0.0071(7) 0.0032(8) O3 0.0238(10) 0.0153(10) 0.0168(9) -0.0009(8) 0.0063(7) -0.0003(8) O4 0.0331(11) 0.0172(10) 0.0188(9) 0.0040(8) 0.0073(8) 0.0009(8) O5 0.0224(9) 0.0368(16) 0.0293(10) 0.0034(10) 0.0116(8) 0.0033(9) O6 0.0258(11) 0.0290(13) 0.0222(11) -0.0025(9) 0.0070(9) -0.0018(9) O7 0.0368(13) 0.0301(13) 0.0287(12) 0.0020(10) 0.0186(10) 0.0063(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 _geom_angle_publ_flag O3 Cu1 O1 178.45(9) . . ? O3 Cu1 N2 84.86(9) . . ? O1 Cu1 N2 94.18(9) . . ? O3 Cu1 N1 95.43(9) . . ? O1 Cu1 N1 85.23(8) . . ? N2 Cu1 N1 167.23(9) . . ? N1 C1 C2 105.2(2) . . ? N1 C1 H1A 110.7 . . ? C2 C1 H1A 110.7 . . ? N1 C1 H1B 110.7 . . ? C2 C1 H1B 110.7 . . ? H1A C1 H1B 108.8 . . ? C1 C2 C3 102.9(2) . . ? C1 C2 H2A 111.2 . . ? C3 C2 H2A 111.2 . . ? C1 C2 H2B 111.2 . . ? C3 C2 H2B 111.2 . . ? H2A C2 H2B 109.1 . . ? C2 C3 C4 102.9(3) . . ? C2 C3 H3A 111.2 . . ? C4 C3 H3A 111.2 . . ? C2 C3 H3B 111.2 . . ? C4 C3 H3B 111.2 . . ? H3A C3 H3B 109.1 . . ? N1 C4 C5 111.08(19) . . ? N1 C4 C3 105.1(2) . . ? C5 C4 C3 111.9(3) . . ? N1 C4 H4 109.6 . . ? C5 C4 H4 109.6 . . ? C3 C4 H4 109.6 . . ? O2 C5 O1 122.7(2) . . ? O2 C5 C4 119.5(2) . . ? O1 C5 C4 117.7(2) . . ? N2 C6 C7 108.7(2) . . ? N2 C6 C8 112.7(2) . . ? C7 C6 C8 109.6(2) . . ? N2 C6 H6 108.6 . . ? C7 C6 H6 108.6 . . ? C8 C6 H6 108.6 . . ? O4 C7 O3 123.3(3) . . ? O4 C7 C6 119.0(2) . . ? O3 C7 C6 117.7(2) . . ? C9 C8 C6 116.2(2) . . ? C9 C8 H8A 108.2 . . ? C6 C8 H8A 108.2 . . ? C9 C8 H8B 108.2 . . ? C6 C8 H8B 108.2 . . ? H8A C8 H8B 107.4 . . ? C14 C9 C10 118.1(3) . . ? C14 C9 C8 121.0(2) . . ? C10 C9 C8 120.8(3) . . ? C9 C10 C11 121.1(3) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C12 C11 C10 119.8(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? O5 C12 C13 122.6(3) . . ? O5 C12 C11 117.4(3) . . ? C13 C12 C11 120.1(2) . . ? C12 C13 C14 119.8(3) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C9 C14 C13 121.2(3) . . ? C9 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C4 N1 C1 108.11(19) . . ? C4 N1 Cu1 109.42(17) . . ? C1 N1 Cu1 112.53(15) . . ? C4 N1 H1 108.9 . . ? C1 N1 H1 108.9 . . ? Cu1 N1 H1 108.9 . . ? C6 N2 Cu1 108.90(16) . . ? C6 N2 H2C 109.9 . . ? Cu1 N2 H2C 109.9 . . ? C6 N2 H2D 109.9 . . ? Cu1 N2 H2D 109.9 . . ? H2C N2 H2D 108.3 . . ? C5 O1 Cu1 115.62(17) . . ? C7 O3 Cu1 114.36(18) . . ? C12 O5 H5 109.5 . . ? H6A O6 H6B 108(4) . . ? H7A O7 H7B 110(5) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.949(2) . ? Cu1 O1 1.9549(19) . ? Cu1 N2 1.978(2) . ? Cu1 N1 2.002(2) . ? C1 N1 1.503(3) . ? C1 C2 1.520(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.523(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.542(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.498(3) . ? C4 C5 1.521(4) . ? C4 H4 1.0000 . ? C5 O2 1.246(3) . ? C5 O1 1.279(3) . ? C6 N2 1.484(3) . ? C6 C7 1.525(4) . ? C6 C8 1.535(4) . ? C6 H6 1.0000 . ? C7 O4 1.238(3) . ? C7 O3 1.283(3) . ? C8 C9 1.515(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.391(4) . ? C9 C10 1.394(4) . ? C10 C11 1.397(4) . ? C10 H10 0.9500 . ? C11 C12 1.386(4) . ? C11 H11 0.9500 . ? C12 O5 1.374(3) . ? C12 C13 1.382(4) . ? C13 C14 1.397(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? N1 H1 1.0000 . ? N2 H2C 0.9100 . ? N2 H2D 0.9100 . ? O5 H5 0.8400 . ? O6 H6A 0.90(4) . ? O6 H6B 0.83(5) . ? O7 H7A 0.79(5) . ? O7 H7B 0.77(5) . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 34.0(3) . . . . ? C1 C2 C3 C4 -39.7(3) . . . . ? C2 C3 C4 N1 30.8(3) . . . . ? C2 C3 C4 C5 151.5(2) . . . . ? N1 C4 C5 O2 -170.6(2) . . . . ? C3 C4 C5 O2 72.3(3) . . . . ? N1 C4 C5 O1 11.1(3) . . . . ? C3 C4 C5 O1 -106.0(3) . . . . ? N2 C6 C7 O4 -161.8(2) . . . . ? C8 C6 C7 O4 74.7(3) . . . . ? N2 C6 C7 O3 20.7(3) . . . . ? C8 C6 C7 O3 -102.9(3) . . . . ? N2 C6 C8 C9 -61.2(3) . . . . ? C7 C6 C8 C9 60.0(3) . . . . ? C6 C8 C9 C14 -95.1(3) . . . . ? C6 C8 C9 C10 88.3(3) . . . . ? C14 C9 C10 C11 0.1(4) . . . . ? C8 C9 C10 C11 176.8(3) . . . . ? C9 C10 C11 C12 0.0(4) . . . . ? C10 C11 C12 O5 179.9(2) . . . . ? C10 C11 C12 C13 0.2(4) . . . . ? O5 C12 C13 C14 179.9(3) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? C10 C9 C14 C13 -0.4(4) . . . . ? C8 C9 C14 C13 -177.0(3) . . . . ? C12 C13 C14 C9 0.6(4) . . . . ? C5 C4 N1 C1 -131.2(2) . . . . ? C3 C4 N1 C1 -10.0(3) . . . . ? C5 C4 N1 Cu1 -8.3(2) . . . . ? C3 C4 N1 Cu1 112.9(2) . . . . ? C2 C1 N1 C4 -14.9(3) . . . . ? C2 C1 N1 Cu1 -135.81(19) . . . . ? C7 C6 N2 Cu1 -24.8(2) . . . . ? C8 C6 N2 Cu1 96.9(2) . . . . ? O2 C5 O1 Cu1 173.59(19) . . . . ? C4 C5 O1 Cu1 -8.1(3) . . . . ? O4 C7 O3 Cu1 177.1(2) . . . . ? C6 C7 O3 Cu1 -5.5(3) . . . . ?