#------------------------------------------------------------------------------ #$Date: 2025-01-30 03:54:15 +0200 (Thu, 30 Jan 2025) $ #$Revision: 297533 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573814.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_1573814 _journal_paper_doi 10.1039/D4CP04569F _chemical_formula_moiety 'C28 H38 Cu2 N8, 4(Cl O4)' _chemical_formula_sum 'C28 H38 Cl4 Cu2 N8 O16' _chemical_formula_weight 1011.54 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_date 2025-01-24 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2025-01-27 deposited with the CCDC. 2025-01-29 downloaded from the CCDC. ; _cell_angle_alpha 82.830(4) _cell_angle_beta 75.916(4) _cell_angle_gamma 61.704(4) _cell_formula_units_Z 1 _cell_length_a 8.0801(13) _cell_length_b 8.3872(14) _cell_length_c 16.325(3) _cell_measurement_reflns_used 5435 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 23.17 _cell_measurement_theta_min 2.57 _cell_volume 944.8(3) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'olex2.solve 1.5 (Bourhis et al., 2015)' _diffrn_ambient_temperature 150.15 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1597 _diffrn_reflns_av_unetI/netI 0.1580 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 13716 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.025 _diffrn_reflns_theta_max 25.025 _diffrn_reflns_theta_min 2.573 _exptl_absorpt_coefficient_mu 1.492 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.4128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1127 before and 0.0810 after correction. The Ratio of minimum to maximum transmission is 0.7656. The \l/2 correction factor is Not present. ; _exptl_crystal_colour Blue _exptl_crystal_density_diffrn 1.778 _exptl_crystal_description Plate _exptl_crystal_F_000 516 _exptl_crystal_size_max 0.413 _exptl_crystal_size_mid 0.321 _exptl_crystal_size_min 0.158 _refine_diff_density_max 1.210 _refine_diff_density_min -0.834 _refine_diff_density_rms 0.163 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 248 _refine_ls_number_reflns 3320 _refine_ls_number_restraints 15 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.1672 _refine_ls_R_factor_gt 0.1010 _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^)+(0.0756P)^2^+10.6660P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2081 _refine_ls_wR_factor_ref 0.2360 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2067 _reflns_number_total 3320 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4cp04569f3.cif _cod_data_source_block Cu2L2B4 _cod_database_code 1573814 _shelx_shelxl_version_number 2014/7 _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. ; _olex2_refinement_description ; 1. Restrained distances Cu1-N2 \\sim Cu1-N2A with sigma of 0.02 N2-C7 \\sim N2A-C7 with sigma of 0.02 N2-C6 \\sim N2A-C6 with sigma of 0.02 2. Uiso/Uaniso restraints and constraints Uanis(N2A) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 3. Rigid body (RIGU) restrains Cu1, O8 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 4. Others Sof(H7BC)=Sof(H7BD)=Sof(H6BC)=Sof(H6BD)=Sof(N2A)=Sof(H2AA)=1-FVAR(1) Sof(N2)=Sof(H2A)=Sof(H7AA)=Sof(H7AB)=Sof(H6AA)=Sof(H6AB)=FVAR(1) 5.a Ternary CH refined with riding coordinates: N2(H2A), N2A(H2AA) 5.b Secondary CH2 refined with riding coordinates: N4(H4A,H4B), C7(H7AA,H7AB), C7(H7BC,H7BD), C6(H6AA,H6AB), C6(H6BC,H6BD), C13(H13A,H13B), C14(H14A,H14B) 5.c Aromatic/amide H refined with riding coordinates: C4(H4), C3(H3), C2(H2), C1(H1), C12(H12), C11(H11), C10(H10), C9(H9) 5.d Fitted hexagon refined as free rotating group: N1(C5,C4,C3,C2,C1), N3(C12,C11,C10,C9,C8) ; _shelx_res_file ; try_a.res created by SHELXL-2014/7 TITL TRY_a.res in P-1 REM Old TITL TRY in P1 REM SHELXT solution in P-1 REM R1 0.223, Rweak 0.079, Alpha 0.118, Orientation as input REM Formula found by SHELXT: C24 Cl2 Cu N2 REM ##### CELL 0.71073 8.0801 8.3872 16.3253 82.83 75.916 61.704 ZERR 1 0.0013 0.0014 0.0027 0.004 0.004 0.004 LATT 1 SFAC C H Cl Cu N O UNIT 28 38 4 2 8 16 SADI Cu1 N2 Cu1 N2A SADI N2 C7 N2A C7 SADI N2 C6 N2A C6 ISOR 0.005 0.01 N2A N2 RIGU Cu1 O8 L.S. 80 PLAN 5 TEMP -123 CONF BOND $H LIST 6 MORE -1 fmap 2 acta SHEL 0.84 15 REM REM REM WGHT 0.075600 10.666000 FVAR 0.46035 0.72060 CU1 4 0.781926 0.337242 0.750916 11.00000 0.02878 0.01700 = 0.01954 -0.00158 -0.00552 -0.00050 AFIX 66 N1 5 0.683055 0.583825 0.793190 11.00000 0.01718 0.01680 = 0.03312 -0.00181 0.00871 -0.00373 C5 1 0.575035 0.719436 0.741943 11.00000 0.01822 0.02582 = 0.02541 0.00648 0.00533 -0.00541 C4 1 0.495139 0.900116 0.763496 11.00000 0.01938 0.02424 = 0.04760 0.00369 0.00405 -0.00481 AFIX 43 H4 2 0.421312 0.992799 0.728471 11.00000 -1.20000 AFIX 65 C3 1 0.523265 0.945187 0.836297 11.00000 0.02355 0.01815 = 0.07089 -0.00345 0.00076 -0.00292 AFIX 43 H3 2 0.468660 1.068674 0.851027 11.00000 -1.20000 AFIX 65 C2 1 0.631285 0.809578 0.887544 11.00000 0.03695 0.03181 = 0.04057 -0.02309 0.00704 -0.01356 AFIX 43 H2 2 0.650507 0.840383 0.937300 11.00000 -1.20000 AFIX 65 C1 1 0.711181 0.628898 0.865992 11.00000 0.03916 0.03020 = 0.01627 -0.00970 0.00700 -0.01047 AFIX 43 H1 2 0.785008 0.536215 0.901017 11.00000 -1.20000 AFIX 0 CL1 3 0.278796 0.481012 0.877598 11.00000 0.03097 0.02114 = 0.02032 -0.00697 -0.00269 -0.00903 O1 6 0.159909 0.389710 0.899412 11.00000 0.03540 0.04868 = 0.06032 -0.00448 0.00554 -0.03233 O2 6 0.471562 0.348151 0.845424 11.00000 0.02773 0.04831 = 0.11787 -0.03469 0.00761 -0.01169 CL2 3 1.208741 0.286551 0.610667 11.00000 0.02840 0.02328 = 0.03764 -0.00428 -0.01052 -0.00716 PART 1 N2 5 0.592856 0.462450 0.674899 21.00000 0.02492 0.02224 = 0.01688 0.00013 0.00221 -0.00737 AFIX 13 H2A 2 0.471120 0.460164 0.706218 21.00000 -1.20000 AFIX 0 PART 0 O3 6 0.216418 0.617013 0.815503 11.00000 0.05188 0.05439 = 0.05786 0.02418 -0.02453 -0.02300 AFIX 66 N3 5 0.834521 0.121495 0.690596 11.00000 0.01568 0.02648 = 0.02886 -0.00991 0.00474 -0.00611 C12 1 0.943546 -0.059422 0.710416 11.00000 0.01749 0.03235 = 0.02780 -0.00613 0.00380 -0.00913 AFIX 43 H12 2 0.998265 -0.090647 0.759010 11.00000 -1.20000 AFIX 65 C11 1 0.972510 -0.194652 0.659134 11.00000 0.02974 0.02656 = 0.03782 -0.01448 0.00425 -0.01165 AFIX 43 H11 2 1.047023 -0.318300 0.672681 11.00000 -1.20000 AFIX 65 C10 1 0.892449 -0.148966 0.588033 11.00000 0.04452 0.05335 = 0.02344 -0.02710 0.01509 -0.03620 AFIX 43 H10 2 0.912244 -0.241391 0.552984 11.00000 -1.20000 AFIX 65 C9 1 0.783424 0.031950 0.568212 11.00000 0.05642 0.04079 = 0.01982 -0.00802 -0.00091 -0.03070 AFIX 43 H9 2 0.728706 0.063173 0.519617 11.00000 -1.20000 AFIX 65 C8 1 0.754459 0.167182 0.619492 11.00000 0.02751 0.04220 = 0.02409 0.00787 -0.00840 -0.02479 AFIX 0 O4 6 0.280260 0.557295 0.948217 11.00000 0.15001 0.08539 = 0.03568 -0.00269 -0.02102 -0.07989 N4 5 0.967725 0.207258 0.824993 11.00000 0.02394 0.02121 = 0.02933 0.00040 -0.00560 -0.00410 AFIX 23 H4A 2 1.071860 0.113037 0.795797 11.00000 -1.20000 H4B 2 1.008579 0.283708 0.837512 11.00000 -1.20000 AFIX 0 O5 6 1.268618 0.316099 0.680438 11.00000 0.10485 0.05474 = 0.04069 -0.00510 -0.02015 -0.03846 O7 6 1.307436 0.327132 0.536334 11.00000 0.10994 0.14600 = 0.02578 0.00914 -0.00708 -0.08726 C7 1 0.652754 0.360770 0.601218 11.00000 0.04204 0.04339 = 0.03244 0.00302 -0.01539 -0.02557 PART 1 AFIX 23 H7AA 2 0.738524 0.396600 0.557685 21.00000 -1.20000 H7AB 2 0.539245 0.386664 0.578630 21.00000 -1.20000 AFIX 23 PART 2 H7BC 2 0.688893 0.381476 0.539894 -21.00000 -1.20000 H7BD 2 0.512729 0.400150 0.615513 -21.00000 -1.20000 AFIX 0 PART 0 O6 6 1.245541 0.102886 0.610556 11.00000 0.07729 0.03459 = 0.07324 -0.01382 -0.02769 -0.02124 C6 1 0.549585 0.654203 0.668830 11.00000 0.02749 0.03476 = 0.04024 0.01004 -0.00744 -0.01208 PART 1 AFIX 23 H6AA 2 0.633944 0.672244 0.617394 21.00000 -1.20000 H6AB 2 0.414969 0.728554 0.662303 21.00000 -1.20000 AFIX 23 PART 2 H6BC 2 0.420395 0.660570 0.681520 -21.00000 -1.20000 H6BD 2 0.556092 0.734862 0.619759 -21.00000 -1.20000 AFIX 0 PART 0 C13 1 0.891829 0.134962 0.906366 11.00000 0.03247 0.02171 = 0.02091 -0.00394 -0.00488 -0.01195 AFIX 23 H13A 2 0.846287 0.052254 0.893234 11.00000 -1.20000 H13B 2 0.780075 0.237131 0.939025 11.00000 -1.20000 AFIX 0 C14 1 1.039243 0.034906 0.960134 11.00000 0.01901 0.02192 = 0.03739 0.00245 -0.01348 -0.00608 AFIX 23 H14A 2 1.151069 -0.067694 0.927770 11.00000 -1.20000 H14B 2 1.084743 0.117339 0.973627 11.00000 -1.20000 AFIX 0 PART 2 N2A 5 0.692924 0.470571 0.646815 -21.00000 0.01949 0.02188 = 0.02311 0.00181 -0.00127 -0.00906 AFIX 13 H2AA 2 0.806308 0.480231 0.609781 -21.00000 -1.20000 AFIX 0 PART 0 O8 6 1.006122 0.398929 0.622722 11.00000 0.05117 0.05201 = 0.14581 -0.00638 -0.02788 -0.00873 HKLF 4 REM TRY_a.res in P-1 REM R1 = 0.1010 for 2067 Fo > 4sig(Fo) and 0.1672 for all 3320 data REM 248 parameters refined using 15 restraints END WGHT 0.0762 10.6154 REM Highest difference peak 1.210, deepest hole -0.834, 1-sigma level 0.163 Q1 1 1.0719 0.4155 0.5479 11.00000 0.05 1.21 Q2 1 0.8512 0.3834 0.7692 11.00000 0.05 0.81 Q3 1 0.6736 0.4557 0.7406 11.00000 0.05 0.78 Q4 1 0.8363 0.1992 0.7581 11.00000 0.05 0.75 Q5 1 1.0974 0.3174 0.6916 11.00000 0.05 0.72 ; _shelx_res_checksum 83339 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 0.78193(18) 0.33724(15) 0.75092(8) 0.0257(4) Uani 1 1 d D . . . . N1 N 0.6831(8) 0.5838(6) 0.7932(4) 0.027(2) Uani 1 1 d G . . . . C5 C 0.5750(9) 0.7194(8) 0.7419(3) 0.028(3) Uani 1 1 d G . . . . C4 C 0.4951(9) 0.9001(7) 0.7635(4) 0.035(3) Uani 1 1 d G . . . . H4 H 0.4213 0.9928 0.7285 0.042 Uiso 1 1 calc R U . . . C3 C 0.5233(10) 0.9452(6) 0.8363(5) 0.042(3) Uani 1 1 d G . . . . H3 H 0.4687 1.0687 0.8510 0.051 Uiso 1 1 calc R U . . . C2 C 0.6313(10) 0.8096(8) 0.8875(4) 0.038(3) Uani 1 1 d G . . . . H2 H 0.6505 0.8404 0.9373 0.046 Uiso 1 1 calc R U . . . C1 C 0.7112(9) 0.6289(7) 0.8660(3) 0.032(3) Uani 1 1 d G . . . . H1 H 0.7850 0.5362 0.9010 0.039 Uiso 1 1 calc R U . . . Cl1 Cl 0.2788(4) 0.4810(3) 0.87760(15) 0.0253(6) Uani 1 1 d . . . . . O1 O 0.1599(11) 0.3897(10) 0.8994(5) 0.045(2) Uani 1 1 d . . . . . O2 O 0.4716(11) 0.3482(12) 0.8454(7) 0.068(3) Uani 1 1 d . . . . . Cl2 Cl 1.2087(4) 0.2866(3) 0.61067(17) 0.0307(7) Uani 1 1 d . . . . . N2 N 0.5929(17) 0.4625(13) 0.6749(7) 0.024(4) Uani 0.72(3) 1 d D U P A 1 H2A H 0.4711 0.4602 0.7062 0.029 Uiso 0.72(3) 1 calc R U P A 1 O3 O 0.2164(12) 0.6170(11) 0.8155(5) 0.055(2) Uani 1 1 d . . . . . N3 N 0.8345(8) 0.1215(7) 0.6906(3) 0.026(2) Uani 1 1 d G . . . . C12 C 0.9435(9) -0.0594(7) 0.7104(3) 0.028(2) Uani 1 1 d G . . . . H12 H 0.9983 -0.0906 0.7590 0.034 Uiso 1 1 calc R U . . . C11 C 0.9725(9) -0.1947(6) 0.6591(4) 0.033(3) Uani 1 1 d G . . . . H11 H 1.0470 -0.3183 0.6727 0.039 Uiso 1 1 calc R U . . . C10 C 0.8924(10) -0.1490(8) 0.5880(4) 0.036(3) Uani 1 1 d G . . . . H10 H 0.9122 -0.2414 0.5530 0.044 Uiso 1 1 calc R U . . . C9 C 0.7834(10) 0.0319(9) 0.5682(3) 0.036(3) Uani 1 1 d G . . . . H9 H 0.7287 0.0632 0.5196 0.043 Uiso 1 1 calc R U . . . C8 C 0.7545(9) 0.1672(7) 0.6195(4) 0.028(2) Uani 1 1 d G . . . . O4 O 0.2803(18) 0.5573(14) 0.9482(6) 0.079(3) Uani 1 1 d . . . . . N4 N 0.9677(11) 0.2073(11) 0.8250(5) 0.028(2) Uani 1 1 d . . . . . H4A H 1.0719 0.1130 0.7958 0.033 Uiso 1 1 calc R U . . . H4B H 1.0086 0.2837 0.8375 0.033 Uiso 1 1 calc R U . . . O5 O 1.2686(15) 0.3161(12) 0.6804(5) 0.065(3) Uani 1 1 d . . . . . O7 O 1.3074(17) 0.3271(17) 0.5363(6) 0.085(3) Uani 1 1 d . . . . . C7 C 0.6528(16) 0.3608(15) 0.6012(7) 0.036(3) Uani 1 1 d D . . . . H7AA H 0.7385 0.3966 0.5577 0.043 Uiso 0.72(3) 1 calc R U P A 1 H7AB H 0.5392 0.3867 0.5786 0.043 Uiso 0.72(3) 1 calc R U P A 1 H7BC H 0.6889 0.3815 0.5399 0.043 Uiso 0.28(3) 1 calc R U P A 2 H7BD H 0.5127 0.4001 0.6155 0.043 Uiso 0.28(3) 1 calc R U P A 2 O6 O 1.2455(13) 0.1029(11) 0.6106(6) 0.060(3) Uani 1 1 d . . . . . C6 C 0.5496(16) 0.6542(14) 0.6688(7) 0.036(3) Uani 1 1 d D . . . . H6AA H 0.6339 0.6722 0.6174 0.043 Uiso 0.72(3) 1 calc R U P A 1 H6AB H 0.4150 0.7286 0.6623 0.043 Uiso 0.72(3) 1 calc R U P A 1 H6BC H 0.4204 0.6606 0.6815 0.043 Uiso 0.28(3) 1 calc R U P A 2 H6BD H 0.5561 0.7349 0.6198 0.043 Uiso 0.28(3) 1 calc R U P A 2 C13 C 0.8918(14) 0.1350(13) 0.9064(6) 0.025(2) Uani 1 1 d . . . . . H13A H 0.8463 0.0523 0.8932 0.030 Uiso 1 1 calc R U . . . H13B H 0.7801 0.2371 0.9390 0.030 Uiso 1 1 calc R U . . . C14 C 1.0392(14) 0.0349(13) 0.9601(6) 0.026(2) Uani 1 1 d . . . . . H14A H 1.1511 -0.0677 0.9278 0.032 Uiso 1 1 calc R U . . . H14B H 1.0847 0.1173 0.9736 0.032 Uiso 1 1 calc R U . . . N2A N 0.693(4) 0.471(2) 0.6468(13) 0.023(10) Uani 0.28(3) 1 d D U P A 2 H2AA H 0.8063 0.4802 0.6098 0.027 Uiso 0.28(3) 1 calc R U P A 2 O8 O 1.0061(14) 0.3989(13) 0.6227(8) 0.087(4) 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 Cu1 0.0288(8) 0.0170(7) 0.0195(7) -0.0016(5) -0.0055(5) -0.0005(5) N1 0.017(4) 0.017(4) 0.033(5) -0.002(4) 0.009(4) -0.004(4) C5 0.018(5) 0.026(6) 0.025(6) 0.006(5) 0.005(5) -0.005(5) C4 0.019(6) 0.024(6) 0.048(7) 0.004(5) 0.004(5) -0.005(5) C3 0.024(6) 0.018(6) 0.071(9) -0.003(6) 0.001(6) -0.003(5) C2 0.037(7) 0.032(6) 0.041(7) -0.023(6) 0.007(6) -0.014(6) C1 0.039(7) 0.030(6) 0.016(6) -0.010(5) 0.007(5) -0.010(5) Cl1 0.0310(14) 0.0211(12) 0.0203(13) -0.0070(10) -0.0027(11) -0.0090(11) O1 0.035(5) 0.049(5) 0.060(6) -0.004(4) 0.006(4) -0.032(4) O2 0.028(5) 0.048(5) 0.118(9) -0.035(6) 0.008(5) -0.012(4) Cl2 0.0284(15) 0.0233(13) 0.0376(16) -0.0043(11) -0.0105(12) -0.0072(12) N2 0.025(6) 0.022(5) 0.017(5) 0.000(4) 0.002(4) -0.007(4) O3 0.052(5) 0.054(5) 0.058(6) 0.024(5) -0.025(5) -0.023(5) N3 0.016(4) 0.026(5) 0.029(5) -0.010(4) 0.005(4) -0.006(4) C12 0.017(5) 0.032(6) 0.028(6) -0.006(5) 0.004(5) -0.009(5) C11 0.030(6) 0.027(6) 0.038(7) -0.014(5) 0.004(5) -0.012(5) C10 0.045(7) 0.053(8) 0.023(6) -0.027(5) 0.015(5) -0.036(6) C9 0.056(8) 0.041(7) 0.020(6) -0.008(5) -0.001(5) -0.031(6) C8 0.028(6) 0.042(7) 0.024(6) 0.008(5) -0.008(5) -0.025(5) O4 0.150(10) 0.085(7) 0.036(5) -0.003(5) -0.021(6) -0.080(8) N4 0.024(5) 0.021(4) 0.029(5) 0.000(4) -0.006(4) -0.004(4) O5 0.105(8) 0.055(6) 0.041(5) -0.005(4) -0.020(5) -0.038(6) O7 0.110(9) 0.146(10) 0.026(5) 0.009(6) -0.007(5) -0.087(8) C7 0.042(7) 0.043(7) 0.032(7) 0.003(5) -0.015(6) -0.026(6) O6 0.077(7) 0.035(5) 0.073(7) -0.014(4) -0.028(5) -0.021(5) C6 0.027(6) 0.035(6) 0.040(7) 0.010(5) -0.007(5) -0.012(5) C13 0.032(6) 0.022(5) 0.021(5) -0.004(4) -0.005(5) -0.012(5) C14 0.019(5) 0.022(5) 0.037(6) 0.002(5) -0.013(5) -0.006(4) N2A 0.019(11) 0.022(11) 0.023(11) 0.002(5) -0.001(5) -0.009(6) O8 0.051(6) 0.052(6) 0.146(11) -0.006(7) -0.028(7) -0.009(5) 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' Cl Cl 0.1484 0.1585 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 84.3(3) . . ? N1 Cu1 N3 165.9(2) . . ? N1 Cu1 N2A 83.4(5) . . ? N3 Cu1 N2 81.6(3) . . ? N3 Cu1 N2A 83.8(5) . . ? N4 Cu1 N1 97.3(3) . . ? N4 Cu1 N2 178.3(4) . . ? N4 Cu1 N3 96.8(3) . . ? N4 Cu1 N2A 156.0(9) . . ? C5 N1 Cu1 113.2(3) . . ? C5 N1 C1 120.0 . . ? C1 N1 Cu1 126.8(3) . . ? N1 C5 C4 120.0 . . ? N1 C5 C6 114.7(5) . . ? C4 C5 C6 125.2(5) . . ? C5 C4 H4 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C3 H3 120.0 . . ? C4 C3 C2 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C2 H2 120.0 . . ? C1 C2 C3 120.0 . . ? C1 C2 H2 120.0 . . ? N1 C1 H1 120.0 . . ? C2 C1 N1 120.0 . . ? C2 C1 H1 120.0 . . ? O2 Cl1 O1 107.7(5) . . ? O3 Cl1 O1 111.4(5) . . ? O3 Cl1 O2 109.3(6) . . ? O4 Cl1 O1 111.4(6) . . ? O4 Cl1 O2 107.6(7) . . ? O4 Cl1 O3 109.4(6) . . ? O7 Cl2 O5 109.3(6) . . ? O7 Cl2 O6 110.0(7) . . ? O7 Cl2 O8 112.2(7) . . ? O6 Cl2 O5 110.0(5) . . ? O6 Cl2 O8 108.2(6) . . ? O8 Cl2 O5 107.1(7) . . ? Cu1 N2 H2A 105.8 . . ? C7 N2 Cu1 110.4(7) . . ? C7 N2 H2A 105.8 . . ? C7 N2 C6 120.5(10) . . ? C6 N2 Cu1 107.4(7) . . ? C6 N2 H2A 105.8 . . ? C12 N3 Cu1 127.4(3) . . ? C12 N3 C8 120.0 . . ? C8 N3 Cu1 112.5(3) . . ? N3 C12 H12 120.0 . . ? N3 C12 C11 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C11 H11 120.0 . . ? C10 C11 C12 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C10 H10 120.0 . . ? C11 C10 C9 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C9 H9 120.0 . . ? C10 C9 C8 120.0 . . ? C8 C9 H9 120.0 . . ? N3 C8 C7 115.8(6) . . ? C9 C8 N3 120.0 . . ? C9 C8 C7 124.1(6) . . ? Cu1 N4 H4A 108.5 . . ? Cu1 N4 H4B 108.5 . . ? H4A N4 H4B 107.5 . . ? C13 N4 Cu1 115.2(6) . . ? C13 N4 H4A 108.5 . . ? C13 N4 H4B 108.5 . . ? N2 C7 C8 110.6(8) . . ? N2 C7 H7AA 109.5 . . ? N2 C7 H7AB 109.5 . . ? C8 C7 H7AA 109.5 . . ? C8 C7 H7AB 109.5 . . ? C8 C7 H7BC 108.9 . . ? C8 C7 H7BD 108.9 . . ? H7AA C7 H7AB 108.1 . . ? H7BC C7 H7BD 107.7 . . ? N2A C7 C8 113.5(10) . . ? N2A C7 H7BC 108.9 . . ? N2A C7 H7BD 108.9 . . ? C5 C6 N2 114.1(8) . . ? C5 C6 H6AA 108.7 . . ? C5 C6 H6AB 108.7 . . ? C5 C6 H6BC 109.1 . . ? C5 C6 H6BD 109.1 . . ? N2 C6 H6AA 108.7 . . ? N2 C6 H6AB 108.7 . . ? H6AA C6 H6AB 107.6 . . ? H6BC C6 H6BD 107.8 . . ? N2A C6 C5 112.7(10) . . ? N2A C6 H6BC 109.1 . . ? N2A C6 H6BD 109.1 . . ? N4 C13 H13A 108.9 . . ? N4 C13 H13B 108.9 . . ? N4 C13 C14 113.2(8) . . ? H13A C13 H13B 107.7 . . ? C14 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C13 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C14 C14 C13 112.1(10) 2_757 . ? C14 C14 H14A 109.2 2_757 . ? C14 C14 H14B 109.2 2_757 . ? H14A C14 H14B 107.9 . . ? Cu1 N2A H2AA 105.7 . . ? C7 N2A Cu1 109.5(11) . . ? C7 N2A C6 120.1(15) . . ? C7 N2A H2AA 105.7 . . ? C6 N2A Cu1 109.1(11) . . ? C6 N2A H2AA 105.7 . . ? 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 N1 1.978(4) . ? Cu1 N2 2.013(10) . ? Cu1 N3 1.984(4) . ? Cu1 N4 1.977(8) . ? Cu1 N2A 2.003(17) . ? N1 C5 1.3900 . ? N1 C1 1.3900 . ? C5 C4 1.3900 . ? C5 C6 1.468(12) . ? C4 H4 0.9500 . ? C4 C3 1.3900 . ? C3 H3 0.9500 . ? C3 C2 1.3900 . ? C2 H2 0.9500 . ? C2 C1 1.3900 . ? C1 H1 0.9500 . ? Cl1 O1 1.449(8) . ? Cl1 O2 1.430(8) . ? Cl1 O3 1.413(8) . ? Cl1 O4 1.392(9) . ? Cl2 O5 1.430(9) . ? Cl2 O7 1.381(10) . ? Cl2 O6 1.424(8) . ? Cl2 O8 1.426(10) . ? N2 H2A 1.0000 . ? N2 C7 1.411(14) . ? N2 C6 1.471(14) . ? N3 C12 1.3900 . ? N3 C8 1.3900 . ? C12 H12 0.9500 . ? C12 C11 1.3900 . ? C11 H11 0.9500 . ? C11 C10 1.3900 . ? C10 H10 0.9500 . ? C10 C9 1.3900 . ? C9 H9 0.9500 . ? C9 C8 1.3900 . ? C8 C7 1.461(12) . ? N4 H4A 0.9100 . ? N4 H4B 0.9100 . ? N4 C13 1.504(13) . ? C7 H7AA 0.9900 . ? C7 H7AB 0.9900 . ? C7 H7BC 0.9900 . ? C7 H7BD 0.9900 . ? C7 N2A 1.44(2) . ? C6 H6AA 0.9900 . ? C6 H6AB 0.9900 . ? C6 H6BC 0.9900 . ? C6 H6BD 0.9900 . ? C6 N2A 1.445(19) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C14 1.507(13) . ? C14 C14 1.48(2) 2_757 ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? N2A H2AA 1.0000 . ? 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 Cu1 N1 C5 C4 179.8(4) . . . . ? Cu1 N1 C5 C6 2.1(6) . . . . ? Cu1 N1 C1 C2 -179.8(5) . . . . ? Cu1 N2 C7 C8 32.5(11) . . . . ? Cu1 N2 C6 C5 -26.1(11) . . . . ? Cu1 N3 C12 C11 -177.4(5) . . . . ? Cu1 N3 C8 C9 177.7(4) . . . . ? Cu1 N3 C8 C7 1.5(7) . . . . ? Cu1 N4 C13 C14 179.2(6) . . . . ? N1 C5 C4 C3 0.0 . . . . ? N1 C5 C6 N2 16.7(11) . . . . ? N1 C5 C6 N2A -20.6(15) . . . . ? C5 N1 C1 C2 0.0 . . . . ? C5 C4 C3 C2 0.0 . . . . ? C5 C6 N2A Cu1 28.4(18) . . . . ? C5 C6 N2A C7 155.9(15) . . . . ? C4 C5 C6 N2 -160.9(7) . . . . ? C4 C5 C6 N2A 161.8(13) . . . . ? C4 C3 C2 C1 0.0 . . . . ? C3 C2 C1 N1 0.0 . . . . ? C1 N1 C5 C4 0.0 . . . . ? C1 N1 C5 C6 -177.7(7) . . . . ? N3 C12 C11 C10 0.0 . . . . ? N3 C8 C7 N2 -22.7(11) . . . . ? N3 C8 C7 N2A 14.9(15) . . . . ? C12 N3 C8 C9 0.0 . . . . ? C12 N3 C8 C7 -176.3(7) . . . . ? C12 C11 C10 C9 0.0 . . . . ? C11 C10 C9 C8 0.0 . . . . ? C10 C9 C8 N3 0.0 . . . . ? C10 C9 C8 C7 176.0(8) . . . . ? C9 C8 C7 N2 161.2(7) . . . . ? C9 C8 C7 N2A -161.2(13) . . . . ? C8 N3 C12 C11 0.0 . . . . ? C8 C7 N2A Cu1 -23.3(18) . . . . ? C8 C7 N2A C6 -150.6(15) . . . . ? N4 C13 C14 C14 -180.0(10) . . . 2_757 ? C7 N2 C6 C5 -153.7(10) . . . . ? C6 C5 C4 C3 177.5(8) . . . . ? C6 N2 C7 C8 158.7(10) . . . . ?