#------------------------------------------------------------------------------ #$Date: 2021-09-25 03:35:26 +0300 (Sat, 25 Sep 2021) $ #$Revision: 269304 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060967.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_7060967 loop_ _publ_author_name 'wu, jialu' 'Li, Bo' 'Wang, Hong' 'Lai, Ying Zhen' 'Ye, Yue' 'Zou, Yongkang' 'Tian, JuMei' _publ_section_title ; How the Magnetic Field Impacts the Chiroptical Activities of Helical Copper Enantiomers ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ03803F _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_block_doi 10.5517/ccdc.csd.cc26f820 _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 102.327(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.3860(2) _cell_length_b 5.69090(10) _cell_length_c 12.4062(2) _cell_measurement_reflns_used 10977 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 71.3650 _cell_measurement_theta_min 3.6470 _cell_volume 785.35(2) _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 100(2) _diffrn_detector_area_resol_mean 10 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.976 _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 0.0519 _diffrn_reflns_av_unetI/netI 0.0288 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 17304 _diffrn_reflns_point_group_measured_fraction_full 0.986 _diffrn_reflns_point_group_measured_fraction_max 0.950 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 71.523 _diffrn_reflns_theta_min 3.647 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 2.347 _exptl_absorpt_correction_T_max 0.440 _exptl_absorpt_correction_T_min 0.373 _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 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 410 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.207 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.049 _refine_ls_abs_structure_details ; Flack x determined using 1227 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.025(15) _refine_ls_extinction_coef 0.0023(4) _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 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 231 _refine_ls_number_reflns 2896 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0229 _refine_ls_R_factor_gt 0.0227 _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^)+(0.0293P)^2^+0.3901P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.0591 _reflns_Friedel_coverage 0.759 _reflns_Friedel_fraction_full 0.972 _reflns_Friedel_fraction_max 0.919 _reflns_number_gt 2862 _reflns_number_total 3047 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03803f2.cif _cod_data_source_block L-1 _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7060967 _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. ; _shelxl_version_number 2014-3 _shelx_res_file ; TITL exp_1890_a.res in P2(1) CELL 1.54184 11.386 5.6909 12.4062 90 102.327 90 ZERR 2 0.0002 0.0001 0.0002 0 0.002 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 WGHT 0.029300 0.390100 EXTI 0.002259 FVAR 8.20476 CU1 3 0.100514 0.336092 0.671610 11.00000 0.01260 0.01013 = 0.00839 0.00015 0.00341 -0.00100 C1 1 0.291686 0.608746 0.605931 11.00000 0.01109 0.01851 = 0.01362 -0.00186 0.00047 -0.00211 AFIX 23 H1A 2 0.326238 0.536114 0.676289 11.00000 -1.20000 H1B 2 0.286861 0.777042 0.616591 11.00000 -1.20000 AFIX 0 C2 1 0.367070 0.553858 0.521268 11.00000 0.01170 0.02127 = 0.01706 -0.00030 0.00413 -0.00466 AFIX 23 H2A 2 0.451747 0.542312 0.555776 11.00000 -1.20000 H2B 2 0.356377 0.672468 0.463846 11.00000 -1.20000 AFIX 0 C3 1 0.316875 0.317100 0.475446 11.00000 0.01096 0.02226 = 0.01753 -0.00433 0.00690 -0.00394 AFIX 23 H3A 2 0.349396 0.190025 0.525005 11.00000 -1.20000 H3B 2 0.334679 0.287557 0.403604 11.00000 -1.20000 AFIX 0 C4 1 0.180336 0.344342 0.467041 11.00000 0.01247 0.01332 = 0.00843 -0.00110 0.00289 -0.00105 AFIX 13 H4 2 0.143471 0.415843 0.396009 11.00000 -1.20000 AFIX 0 C5 1 0.119796 0.110944 0.478905 11.00000 0.00710 0.01262 = 0.01397 0.00183 0.00145 0.00329 C6 1 0.115895 0.271757 0.900416 11.00000 0.01279 0.01336 = 0.00716 -0.00043 0.00238 -0.00107 AFIX 13 H6 2 0.060921 0.243566 0.950003 11.00000 -1.20000 AFIX 0 C7 1 0.117068 0.533883 0.875966 11.00000 0.00689 0.01680 = 0.01199 -0.00021 0.00245 0.00115 C8 1 0.242645 0.191796 0.958403 11.00000 0.01419 0.01181 = 0.01028 0.00058 0.00326 0.00112 AFIX 23 H8A 2 0.265019 0.275420 1.027897 11.00000 -1.20000 H8B 2 0.239234 0.025930 0.975478 11.00000 -1.20000 AFIX 0 C9 1 0.340988 0.227522 0.895037 11.00000 0.01117 0.01458 = 0.00963 0.00170 -0.00050 0.00108 C10 1 0.365902 0.055759 0.822593 11.00000 0.01675 0.01396 = 0.01242 -0.00139 0.00050 -0.00004 AFIX 43 H10 2 0.318303 -0.078435 0.810306 11.00000 -1.20000 AFIX 0 C11 1 0.460348 0.080945 0.768399 11.00000 0.01640 0.01577 = 0.01399 -0.00279 0.00266 0.00188 AFIX 43 H11 2 0.475701 -0.035686 0.720735 11.00000 -1.20000 AFIX 0 C12 1 0.531456 0.281170 0.785933 11.00000 0.01088 0.02131 = 0.01042 0.00220 0.00185 0.00203 C13 1 0.508491 0.454602 0.857158 11.00000 0.01219 0.01505 = 0.01445 0.00113 -0.00102 -0.00252 AFIX 43 H13 2 0.555902 0.589113 0.868725 11.00000 -1.20000 AFIX 0 C14 1 0.414073 0.426534 0.911344 11.00000 0.01621 0.01231 = 0.00989 -0.00168 0.00108 0.00197 AFIX 43 H14 2 0.399493 0.543024 0.959410 11.00000 -1.20000 AFIX 0 N1 4 0.169187 0.508394 0.558658 11.00000 0.01031 0.01104 = 0.00895 -0.00055 0.00139 -0.00063 AFIX 13 H1 2 0.114740 0.636876 0.528416 11.00000 -1.20000 AFIX 0 N2 4 0.070338 0.143871 0.795573 11.00000 0.01198 0.01167 = 0.01095 -0.00092 0.00211 -0.00119 AFIX 23 H2C 2 -0.008114 0.117188 0.787189 11.00000 -1.20000 H2D 2 0.107572 0.006069 0.796858 11.00000 -1.20000 AFIX 0 O1 5 0.087184 0.070673 0.569845 11.00000 0.01362 0.01361 = 0.00961 0.00032 0.00472 -0.00065 O2 5 0.106238 -0.034913 0.401949 11.00000 0.01495 0.01573 = 0.01212 -0.00428 0.00505 -0.00156 O3 5 0.117412 0.595938 0.776160 11.00000 0.01748 0.01075 = 0.01074 0.00118 0.00371 0.00031 O4 5 0.123142 0.676037 0.952660 11.00000 0.02286 0.01223 = 0.01298 -0.00293 0.00444 -0.00146 O5 5 0.623391 0.298027 0.730155 11.00000 0.01558 0.02566 = 0.01911 -0.00244 0.00789 -0.00298 AFIX 147 H5 2 0.663233 0.416173 0.750432 11.00000 -1.50000 AFIX 0 O6 5 0.830900 0.032176 0.832539 11.00000 0.01826 0.02101 = 0.01368 0.00126 0.00402 0.00205 H6A 2 0.766357 0.107309 0.798112 11.00000 -1.50000 H6B 2 0.844604 0.072165 0.895000 11.00000 -1.50000 O7 5 0.808161 0.566903 0.786457 11.00000 0.02452 0.02038 = 0.01892 -0.00203 0.01259 -0.00417 H7A 2 0.818689 0.705708 0.803144 11.00000 -1.50000 H7B 2 0.834068 0.553598 0.733161 11.00000 -1.50000 HKLF 4 REM exp_1890_a.res in P2(1) REM R1 = 0.0227 for 2862 Fo > 4sig(Fo) and 0.0229 for all 2896 data REM 231 parameters refined using 1 restraints END WGHT 0.0296 0.3866 REM Highest difference peak 0.207, deepest hole -0.286, 1-sigma level 0.049 Q1 1 0.2510 0.3341 0.4698 11.00000 0.05 0.21 Q2 1 0.1622 0.6714 0.7649 11.00000 0.05 0.20 Q3 1 0.1412 0.5123 0.7600 11.00000 0.05 0.19 Q4 1 0.3420 0.4234 0.4943 11.00000 0.05 0.19 Q5 1 0.0595 0.1604 0.5841 11.00000 0.05 0.18 ; _shelx_res_checksum 38756 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 0.10051(3) 0.33609(6) 0.67161(3) 0.01020(13) Uani 1 1 d . . . . . C1 C 0.2917(2) 0.6087(6) 0.6059(2) 0.0147(6) Uani 1 1 d . . . . . H1A H 0.3262 0.5361 0.6763 0.018 Uiso 1 1 calc R U . . . H1B H 0.2869 0.7770 0.6166 0.018 Uiso 1 1 calc R U . . . C2 C 0.3671(3) 0.5539(6) 0.5213(2) 0.0165(6) Uani 1 1 d . . . . . H2A H 0.4517 0.5423 0.5558 0.020 Uiso 1 1 calc R U . . . H2B H 0.3564 0.6725 0.4638 0.020 Uiso 1 1 calc R U . . . C3 C 0.3169(2) 0.3171(6) 0.4754(2) 0.0163(6) Uani 1 1 d . . . . . H3A H 0.3494 0.1900 0.5250 0.020 Uiso 1 1 calc R U . . . H3B H 0.3347 0.2876 0.4036 0.020 Uiso 1 1 calc R U . . . C4 C 0.1803(2) 0.3443(6) 0.46704(19) 0.0113(5) Uani 1 1 d . . . . . H4 H 0.1435 0.4158 0.3960 0.014 Uiso 1 1 calc R U . . . C5 C 0.1198(2) 0.1109(5) 0.4789(2) 0.0113(6) Uani 1 1 d . . . . . C6 C 0.1159(3) 0.2718(5) 0.9004(2) 0.0111(6) Uani 1 1 d . . . . . H6 H 0.0609 0.2436 0.9500 0.013 Uiso 1 1 calc R U . . . C7 C 0.1171(2) 0.5339(5) 0.8760(2) 0.0118(6) Uani 1 1 d . . . . . C8 C 0.2426(2) 0.1918(5) 0.9584(2) 0.0120(6) Uani 1 1 d . . . . . H8A H 0.2650 0.2754 1.0279 0.014 Uiso 1 1 calc R U . . . H8B H 0.2392 0.0259 0.9755 0.014 Uiso 1 1 calc R U . . . C9 C 0.3410(3) 0.2275(5) 0.8950(2) 0.0122(6) Uani 1 1 d . . . . . C10 C 0.3659(3) 0.0558(5) 0.8226(2) 0.0148(6) Uani 1 1 d . . . . . H10 H 0.3183 -0.0784 0.8103 0.018 Uiso 1 1 calc R U . . . C11 C 0.4603(3) 0.0809(6) 0.7684(2) 0.0155(6) Uani 1 1 d . . . . . H11 H 0.4757 -0.0357 0.7207 0.019 Uiso 1 1 calc R U . . . C12 C 0.5315(2) 0.2812(5) 0.7859(2) 0.0143(6) Uani 1 1 d . . . . . C13 C 0.5085(3) 0.4546(5) 0.8572(2) 0.0145(6) Uani 1 1 d . . . . . H13 H 0.5559 0.5891 0.8687 0.017 Uiso 1 1 calc R U . . . C14 C 0.4141(3) 0.4265(5) 0.9113(2) 0.0131(6) Uani 1 1 d . . . . . H14 H 0.3995 0.5430 0.9594 0.016 Uiso 1 1 calc R U . . . N1 N 0.1692(2) 0.5084(4) 0.55866(18) 0.0102(5) Uani 1 1 d . . . . . H1 H 0.1147 0.6369 0.5284 0.012 Uiso 1 1 calc R U . . . N2 N 0.0703(2) 0.1439(4) 0.79557(19) 0.0116(5) Uani 1 1 d . . . . . H2C H -0.0081 0.1172 0.7872 0.014 Uiso 1 1 calc R U . . . H2D H 0.1076 0.0061 0.7969 0.014 Uiso 1 1 calc R U . . . O1 O 0.08718(17) 0.0707(4) 0.56985(15) 0.0119(4) Uani 1 1 d . . . . . O2 O 0.10624(18) -0.0349(4) 0.40195(16) 0.0139(4) Uani 1 1 d . . . . . O3 O 0.11741(18) 0.5959(4) 0.77616(15) 0.0129(4) Uani 1 1 d . . . . . O4 O 0.12314(19) 0.6760(4) 0.95266(16) 0.0159(4) Uani 1 1 d . . . . . O5 O 0.62339(18) 0.2980(4) 0.73015(17) 0.0195(5) Uani 1 1 d . . . . . H5 H 0.6632 0.4162 0.7504 0.029 Uiso 1 1 calc R U . . . O6 O 0.8309(2) 0.0322(4) 0.83254(19) 0.0176(5) Uani 1 1 d . . . . . H6A H 0.766(4) 0.107(8) 0.798(3) 0.026 Uiso 1 1 d . U . . . H6B H 0.845(3) 0.072(8) 0.895(4) 0.026 Uiso 1 1 d . U . . . O7 O 0.8082(2) 0.5669(4) 0.7865(2) 0.0201(5) Uani 1 1 d . . . . . H7A H 0.819(4) 0.706(9) 0.803(4) 0.030 Uiso 1 1 d . U . . . H7B H 0.834(4) 0.554(8) 0.733(4) 0.030 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 0.0126(2) 0.0101(2) 0.00839(19) 0.00015(16) 0.00341(13) -0.00100(16) C1 0.0111(13) 0.0185(15) 0.0136(13) -0.0019(12) 0.0005(11) -0.0021(11) C2 0.0117(13) 0.0213(17) 0.0171(14) -0.0003(12) 0.0041(11) -0.0047(12) C3 0.0110(12) 0.0223(16) 0.0175(13) -0.0043(14) 0.0069(10) -0.0039(14) C4 0.0125(12) 0.0133(13) 0.0084(11) -0.0011(13) 0.0029(9) -0.0010(14) C5 0.0071(12) 0.0126(14) 0.0140(14) 0.0018(12) 0.0015(10) 0.0033(11) C6 0.0128(13) 0.0134(16) 0.0072(12) -0.0004(10) 0.0024(10) -0.0011(10) C7 0.0069(12) 0.0168(16) 0.0120(13) -0.0002(12) 0.0024(10) 0.0012(11) C8 0.0142(14) 0.0118(14) 0.0103(13) 0.0006(11) 0.0033(11) 0.0011(11) C9 0.0112(13) 0.0146(14) 0.0096(13) 0.0017(11) -0.0005(10) 0.0011(11) C10 0.0167(14) 0.0140(16) 0.0124(13) -0.0014(11) 0.0005(10) 0.0000(12) C11 0.0164(14) 0.0158(15) 0.0140(14) -0.0028(12) 0.0027(11) 0.0019(12) C12 0.0109(13) 0.0213(17) 0.0104(12) 0.0022(11) 0.0018(10) 0.0020(11) C13 0.0122(13) 0.0150(15) 0.0145(14) 0.0011(12) -0.0010(11) -0.0025(11) C14 0.0162(14) 0.0123(13) 0.0099(13) -0.0017(11) 0.0011(11) 0.0020(11) N1 0.0103(11) 0.0110(11) 0.0089(11) -0.0006(9) 0.0014(9) -0.0006(9) N2 0.0120(11) 0.0117(13) 0.0109(12) -0.0009(10) 0.0021(9) -0.0012(9) O1 0.0136(10) 0.0136(10) 0.0096(9) 0.0003(8) 0.0047(7) -0.0006(8) O2 0.0150(10) 0.0157(11) 0.0121(10) -0.0043(8) 0.0050(8) -0.0016(8) O3 0.0175(10) 0.0107(10) 0.0107(9) 0.0012(8) 0.0037(8) 0.0003(8) O4 0.0229(11) 0.0122(10) 0.0130(10) -0.0029(8) 0.0044(8) -0.0015(8) O5 0.0156(10) 0.0257(15) 0.0191(10) -0.0024(9) 0.0079(8) -0.0030(9) O6 0.0183(11) 0.0210(12) 0.0137(10) 0.0013(9) 0.0040(9) 0.0020(9) O7 0.0245(12) 0.0204(13) 0.0189(11) -0.0020(10) 0.0126(10) -0.0042(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 178.33(9) . . ? O3 Cu1 N2 84.89(9) . . ? O1 Cu1 N2 94.16(9) . . ? O3 Cu1 N1 95.53(9) . . ? O1 Cu1 N1 85.09(9) . . ? N2 Cu1 N1 167.17(10) . . ? N1 C1 C2 105.4(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 102.5(2) . . ? C1 C2 H2A 111.3 . . ? C3 C2 H2A 111.3 . . ? C1 C2 H2B 111.3 . . ? C3 C2 H2B 111.3 . . ? H2A C2 H2B 109.2 . . ? C2 C3 C4 103.2(3) . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3B 111.1 . . ? C4 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? N1 C4 C5 111.0(2) . . ? N1 C4 C3 105.0(2) . . ? C5 C4 C3 112.2(3) . . ? N1 C4 H4 109.5 . . ? C5 C4 H4 109.5 . . ? C3 C4 H4 109.5 . . ? O2 C5 O1 122.8(3) . . ? O2 C5 C4 119.5(2) . . ? O1 C5 C4 117.7(2) . . ? N2 C6 C7 108.8(2) . . ? N2 C6 C8 112.5(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 123.2(3) . . ? O4 C7 C6 119.2(3) . . ? O3 C7 C6 117.5(3) . . ? 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 117.7(3) . . ? C14 C9 C8 121.2(3) . . ? C10 C9 C8 121.0(3) . . ? C11 C10 C9 121.5(3) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C12 C11 C10 119.6(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? O5 C12 C13 122.6(3) . . ? O5 C12 C11 117.4(3) . . ? C13 C12 C11 120.1(3) . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C9 121.4(3) . . ? C13 C14 H14 119.3 . . ? C9 C14 H14 119.3 . . ? C4 N1 C1 108.1(2) . . ? C4 N1 Cu1 109.59(18) . . ? C1 N1 Cu1 112.40(16) . . ? C4 N1 H1 108.9 . . ? C1 N1 H1 108.9 . . ? Cu1 N1 H1 108.9 . . ? C6 N2 Cu1 108.92(17) . . ? 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 115.69(18) . . ? C7 O3 Cu1 114.30(19) . . ? C12 O5 H5 109.5 . . ? H6A O6 H6B 108(4) . . ? H7A O7 H7B 104(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 1.954(2) . ? Cu1 N2 1.976(2) . ? Cu1 N1 2.001(2) . ? C1 N1 1.505(4) . ? C1 C2 1.524(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.525(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.544(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N1 1.497(4) . ? C4 C5 1.518(4) . ? C4 H4 0.9800 . ? C5 O2 1.250(4) . ? C5 O1 1.281(3) . ? C6 N2 1.484(4) . ? C6 C7 1.523(4) . ? C6 C8 1.538(4) . ? C6 H6 0.9800 . ? C7 O4 1.240(4) . ? C7 O3 1.288(3) . ? C8 C9 1.513(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.394(4) . ? C9 C10 1.397(4) . ? C10 C11 1.392(4) . ? C10 H10 0.9300 . ? C11 C12 1.388(4) . ? C11 H11 0.9300 . ? C12 O5 1.376(3) . ? C12 C13 1.386(4) . ? C13 C14 1.393(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? N1 H1 0.9800 . ? N2 H2C 0.8900 . ? N2 H2D 0.8900 . ? O5 H5 0.8200 . ? O6 H6A 0.88(5) . ? O6 H6B 0.79(4) . ? O7 H7A 0.82(5) . ? O7 H7B 0.78(4) . ? 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 -30.9(3) . . . . ? C2 C3 C4 C5 -151.5(2) . . . . ? N1 C4 C5 O2 170.4(2) . . . . ? C3 C4 C5 O2 -72.5(3) . . . . ? N1 C4 C5 O1 -11.2(3) . . . . ? C3 C4 C5 O1 105.9(3) . . . . ? N2 C6 C7 O4 162.3(2) . . . . ? C8 C6 C7 O4 -74.3(3) . . . . ? N2 C6 C7 O3 -20.9(3) . . . . ? C8 C6 C7 O3 102.5(3) . . . . ? N2 C6 C8 C9 61.2(3) . . . . ? C7 C6 C8 C9 -60.0(3) . . . . ? C6 C8 C9 C14 95.2(3) . . . . ? C6 C8 C9 C10 -88.3(3) . . . . ? C14 C9 C10 C11 0.1(4) . . . . ? C8 C9 C10 C11 -176.5(3) . . . . ? C9 C10 C11 C12 -0.3(4) . . . . ? C10 C11 C12 O5 -179.8(2) . . . . ? C10 C11 C12 C13 0.1(4) . . . . ? O5 C12 C13 C14 -179.9(3) . . . . ? C11 C12 C13 C14 0.3(4) . . . . ? C12 C13 C14 C9 -0.4(4) . . . . ? C10 C9 C14 C13 0.3(4) . . . . ? C8 C9 C14 C13 176.8(3) . . . . ? C5 C4 N1 C1 131.2(2) . . . . ? C3 C4 N1 C1 9.8(3) . . . . ? C5 C4 N1 Cu1 8.4(2) . . . . ? C3 C4 N1 Cu1 -113.0(2) . . . . ? C2 C1 N1 C4 15.1(3) . . . . ? C2 C1 N1 Cu1 136.2(2) . . . . ? C7 C6 N2 Cu1 24.9(3) . . . . ? C8 C6 N2 Cu1 -96.7(2) . . . . ? O2 C5 O1 Cu1 -173.4(2) . . . . ? C4 C5 O1 Cu1 8.3(3) . . . . ? O4 C7 O3 Cu1 -177.7(2) . . . . ? C6 C7 O3 Cu1 5.7(3) . . . . ?