#------------------------------------------------------------------------------ #$Date: 2025-01-30 03:54:15 +0200 (Thu, 30 Jan 2025) $ #$Revision: 297533 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573815.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_1573815 _journal_paper_doi 10.1039/D4CP04569F _chemical_formula_moiety 'C32 H46 Cl4 Cu2 N8 O16, 2(C2 H3 N)' _chemical_formula_sum 'C36 H52 Cl4 Cu2 N10 O16' _chemical_formula_weight 1149.75 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2024-09-05 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2024-09-05 deposited with the CCDC. 2025-01-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.215(6) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 17.628(4) _cell_length_b 8.5678(18) _cell_length_c 15.791(3) _cell_measurement_reflns_used 4437 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 28.05 _cell_measurement_theta_min 2.31 _cell_volume 2381.2(9) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.1656 _diffrn_reflns_av_unetI/netI 0.0973 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 29525 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.027 _diffrn_reflns_theta_max 25.027 _diffrn_reflns_theta_min 2.314 _exptl_absorpt_coefficient_mu 1.196 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.5080 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour Block _exptl_crystal_density_diffrn 1.604 _exptl_crystal_description Blue _exptl_crystal_F_000 1184 _exptl_crystal_size_max 0.097 _exptl_crystal_size_mid 0.071 _exptl_crystal_size_min 0.054 _refine_diff_density_max 0.673 _refine_diff_density_min -0.730 _refine_diff_density_rms 0.111 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 331 _refine_ls_number_reflns 4205 _refine_ls_number_restraints 67 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.1207 _refine_ls_R_factor_gt 0.0689 _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^)+(0.0942P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1601 _refine_ls_wR_factor_ref 0.1895 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2664 _reflns_number_total 4205 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4cp04569f3.cif _cod_data_source_block Cu2L2B8 _cod_original_cell_volume 2381.2(8) _cod_database_code 1573815 _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. ; _shelx_estimated_absorpt_t_max 0.938 _shelx_estimated_absorpt_t_min 0.893 _olex2_refinement_description ; 1. Restrained distances Cl2-O5 \\sim Cl2-O5A with sigma of 0.02 Cu1-N2 \\sim Cu1-N2A with sigma of 0.02 Cl2-O6 \\sim Cl2-O6A with sigma of 0.02 N2-C6 \\sim N2A-C6 with sigma of 0.02 N2-C7 \\sim N2A-C7 with sigma of 0.02 Cl2-O7 \\sim Cl2-O7A with sigma of 0.02 Cl2-O8 \\sim Cl2-O8A with sigma of 0.02 2. Uiso/Uaniso restraints and constraints Uanis(N2) \\sim Ueq, Uanis(N2A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 Uanis(O7A) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(O6A) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O5A) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(O8A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 Uanis(O6) = Uanis(O6A) Uanis(O8A) = Uanis(O8) Uanis(O5A) = Uanis(O5) Uanis(O7A) = Uanis(O7) 3. Others Sof(O7A)=Sof(O5A)=Sof(O8A)=Sof(O6A)=1-FVAR(1) Sof(O5)=Sof(O6)=Sof(O7)=Sof(O8)=FVAR(1) Sof(H6BC)=Sof(H6BD)=Sof(H7BC)=Sof(H7BD)=Sof(N2A)=Sof(H2AA)=1-FVAR(2) Sof(N2)=Sof(H2)=Sof(H6AA)=Sof(H6AB)=Sof(H7AA)=Sof(H7AB)=FVAR(2) 4.a Ternary CH refined with riding coordinates: N2(H2), N2A(H2AA) 4.b Secondary CH2 refined with riding coordinates: C6(H6AA,H6AB), C6(H6BC,H6BD), C7(H7AA,H7AB), C7(H7BC,H7BD), N4(H4A,H4B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B) 4.c Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2A), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12) 4.d Idealised Me refined as rotating group: C18(H18A,H18B,H18C) ; _shelx_res_file ; TRY_a.res created by SHELXL-2014/7 TITL TRY_a.res in P2(1)/c REM Old TITL TRY in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.223, Rweak 0.032, Alpha 0.059, Orientation as input REM Formula found by SHELXT: C27 Cl2 Cu N5 CELL 0.71073 17.6282 8.5678 15.7908 90 93.215 90 ZERR 2 0.0037 0.0018 0.0031 0 0.006 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl Cu N O UNIT 72 104 8 4 20 32 SADI Cl2 O5 Cl2 O5A SADI Cu1 N2 Cu1 N2A SADI Cl2 O6 Cl2 O6A SADI N2 C6 N2A C6 SADI N2 C7 N2A C7 SADI Cl2 O7 Cl2 O7A SADI Cl2 O8 Cl2 O8A ISOR 0.005 0.01 N2 N2A EADP O6 O6A EADP O8A O8 EADP O5A O5 EADP O7A O7 ISOR 0.005 0.01 O7A O7 O6A O6 O5 O5A O8 O8A L.S. 10 PLAN 20 SIZE 0.054 0.071 0.097 TEMP -123.15 CONF ACTA BOND $H LIST 6 FMAP 2 MORE -1 SHEL 0.84 15 REM REM REM WGHT 0.094237 FVAR 0.31757 0.75483 0.64378 CL1 3 0.337059 0.269524 0.287410 11.00000 0.05791 0.04571 = 0.02996 0.00154 0.00636 -0.00692 O1 6 0.367974 0.130143 0.252478 11.00000 0.10202 0.05002 = 0.06499 -0.01572 0.02954 -0.00279 N1 5 0.175081 0.155571 0.484952 11.00000 0.04718 0.02893 = 0.02830 0.00321 0.00537 0.00647 C1 1 0.202020 0.058168 0.546788 11.00000 0.05222 0.03924 = 0.04107 -0.00319 0.00118 -0.00267 AFIX 43 H1 2 0.244005 0.090601 0.582880 11.00000 -1.20000 AFIX 0 CU1 4 0.213070 0.372173 0.456629 11.00000 0.04611 0.02858 = 0.03824 0.00562 -0.00206 -0.00468 O2 6 0.294028 0.353884 0.224565 11.00000 0.07916 0.16002 = 0.04969 0.01879 0.00139 0.04686 PART 1 N2 5 0.116729 0.373534 0.381736 31.00000 0.03880 0.03175 = 0.04176 0.00587 0.00484 -0.00158 AFIX 13 H2 2 0.077795 0.425913 0.415623 31.00000 -1.20000 AFIX 0 PART 0 C2 1 0.170370 -0.087837 0.559352 11.00000 0.06554 0.03542 = 0.04916 0.01458 0.01487 0.00754 AFIX 43 H2A 2 0.191280 -0.154752 0.602590 11.00000 -1.20000 AFIX 0 CL2 3 0.086889 0.427232 0.621679 11.00000 0.06274 0.03334 = 0.06413 -0.00977 0.01301 -0.00637 C3 1 0.108924 -0.134592 0.509075 11.00000 0.05606 0.02954 = 0.07396 0.00446 0.02557 -0.00288 AFIX 43 H3 2 0.085758 -0.233088 0.517456 11.00000 -1.20000 AFIX 0 N3 5 0.227512 0.581656 0.398149 11.00000 0.04580 0.03004 = 0.03361 -0.00039 0.00287 0.00073 O3 6 0.287662 0.229208 0.353979 11.00000 0.13315 0.04882 = 0.05284 -0.00885 0.05634 -0.03155 C4 1 0.081360 -0.035201 0.445833 11.00000 0.04177 0.03435 = 0.05232 -0.00570 0.01195 -0.00567 AFIX 43 H4 2 0.038825 -0.064912 0.409826 11.00000 -1.20000 AFIX 0 N5 5 0.336994 0.740690 0.626942 11.00000 0.08550 0.06665 = 0.06044 -0.01892 -0.00033 0.01708 O4 6 0.396986 0.364538 0.321781 11.00000 0.06726 0.07027 = 0.08515 -0.01900 0.00381 -0.02210 C5 1 0.115907 0.107913 0.435058 11.00000 0.03779 0.02761 = 0.03369 -0.00089 0.00845 0.00285 PART 1 O5 6 0.117231 0.489677 0.546557 21.00000 0.07330 0.06191 = 0.10020 0.02661 0.02870 0.01662 O6 6 0.031475 0.315900 0.599049 21.00000 0.09616 0.07153 = 0.10807 -0.02486 0.01953 -0.04089 PART 0 C6 1 0.088850 0.217840 0.366125 11.00000 0.05672 0.03883 = 0.04974 0.00486 -0.00696 -0.00860 PART 1 AFIX 23 H6AA 2 0.106330 0.180369 0.311205 31.00000 -1.20000 H6AB 2 0.032608 0.219265 0.362164 31.00000 -1.20000 AFIX 23 PART 2 H6BC 2 0.075412 0.158276 0.313691 -31.00000 -1.20000 H6BD 2 0.042737 0.272898 0.383148 -31.00000 -1.20000 AFIX 0 PART 0 C7 1 0.125905 0.474311 0.308141 11.00000 0.04471 0.04222 = 0.04492 0.01526 -0.00241 -0.00610 PART 1 AFIX 23 H7AA 2 0.075845 0.516528 0.287899 31.00000 -1.20000 H7AB 2 0.146404 0.412610 0.261593 31.00000 -1.20000 AFIX 23 PART 2 H7BC 2 0.073981 0.503133 0.323238 -31.00000 -1.20000 H7BD 2 0.124735 0.458231 0.245996 -31.00000 -1.20000 AFIX 0 PART 1 O7 6 0.056891 0.548022 0.671183 21.00000 0.06473 0.06420 = 0.10091 -0.03946 -0.00058 0.01100 PART 0 C8 1 0.179005 0.606461 0.331377 11.00000 0.04174 0.03104 = 0.03404 -0.00109 0.00746 0.00568 PART 1 O8 6 0.151489 0.351034 0.667597 21.00000 0.07939 0.07628 = 0.07338 -0.00739 0.00846 0.02031 PART 0 C9 1 0.177214 0.743214 0.285362 11.00000 0.05263 0.03371 = 0.03525 0.00439 0.01212 0.00733 AFIX 43 H9 2 0.141385 0.756999 0.238749 11.00000 -1.20000 AFIX 0 C10 1 0.228306 0.859611 0.308153 11.00000 0.06888 0.02202 = 0.04671 0.00672 0.01962 0.00941 AFIX 43 H10 2 0.228637 0.954735 0.277265 11.00000 -1.20000 AFIX 0 C11 1 0.278874 0.835418 0.376553 11.00000 0.06084 0.03229 = 0.05347 0.00273 0.01584 -0.00691 AFIX 43 H11 2 0.314482 0.914404 0.393189 11.00000 -1.20000 AFIX 0 C12 1 0.278003 0.697098 0.420932 11.00000 0.05528 0.03718 = 0.04327 -0.00001 0.00246 -0.00583 AFIX 43 H12 2 0.313065 0.681787 0.468107 11.00000 -1.20000 AFIX 0 N4 5 0.289999 0.407208 0.552943 11.00000 0.04606 0.03360 = 0.03419 0.00031 0.00598 0.00100 AFIX 23 H4A 2 0.281139 0.503709 0.574342 11.00000 -1.20000 H4B 2 0.280045 0.337155 0.594191 11.00000 -1.20000 AFIX 0 C13 1 0.372249 0.397365 0.539474 11.00000 0.04061 0.03437 = 0.04331 -0.00160 0.00292 0.00267 AFIX 23 H13A 2 0.400690 0.454634 0.585528 11.00000 -1.20000 H13B 2 0.382452 0.448952 0.485178 11.00000 -1.20000 AFIX 0 C14 1 0.400682 0.232042 0.537548 11.00000 0.05390 0.04418 = 0.04217 0.00000 0.00944 0.00248 AFIX 23 H14A 2 0.369186 0.172049 0.495096 11.00000 -1.20000 H14B 2 0.394996 0.183395 0.593705 11.00000 -1.20000 AFIX 0 C15 1 0.483086 0.222748 0.515786 11.00000 0.04148 0.03593 = 0.05940 -0.00767 0.00437 0.00684 AFIX 23 H15A 2 0.487093 0.257181 0.456358 11.00000 -1.20000 H15B 2 0.513020 0.296418 0.552584 11.00000 -1.20000 AFIX 0 C16 1 0.517783 0.062371 0.525727 11.00000 0.05263 0.06269 = 0.09776 -0.02057 0.00859 0.00769 AFIX 23 H16A 2 0.571800 0.069421 0.512046 11.00000 -1.20000 H16B 2 0.516672 0.031844 0.586112 11.00000 -1.20000 AFIX 0 C17 1 0.381255 0.761494 0.681169 11.00000 0.05876 0.04056 = 0.05336 -0.00357 0.00581 0.00878 C18 1 0.437332 0.781131 0.748542 11.00000 0.06704 0.06845 = 0.06008 -0.00664 0.00544 -0.00134 AFIX 137 H18A 2 0.487484 0.790851 0.725244 11.00000 -1.50000 H18B 2 0.436932 0.690416 0.786317 11.00000 -1.50000 H18C 2 0.426252 0.875668 0.780529 11.00000 -1.50000 AFIX 0 PART 2 O7A 6 0.056682 0.512033 0.691163 -21.00000 0.06473 0.06420 = 0.10091 -0.03946 -0.00058 0.01100 O5A 6 0.145091 0.507846 0.585248 -21.00000 0.07330 0.06191 = 0.10020 0.02661 0.02870 0.01662 O8A 6 0.099057 0.278612 0.660456 -21.00000 0.07939 0.07628 = 0.07338 -0.00739 0.00846 0.02031 O6A 6 0.021790 0.402865 0.562863 -21.00000 0.09616 0.07153 = 0.10807 -0.02486 0.01953 -0.04089 N2A 5 0.147281 0.330211 0.349925 -31.00000 0.03420 0.03167 = 0.03128 -0.00063 0.00465 -0.00337 AFIX 13 H2AA 2 0.181368 0.276401 0.310653 -31.00000 -1.20000 AFIX 0 HKLF 4 REM TRY_a.res in P2(1)/c REM R1 = 0.0689 for 2664 Fo > 4sig(Fo) and 0.1207 for all 4205 data REM 331 parameters refined using 67 restraints END WGHT 0.0896 1.6218 REM Highest difference peak 0.673, deepest hole -0.730, 1-sigma level 0.111 Q1 1 0.5006 0.0683 0.4590 11.00000 0.05 0.67 Q2 1 0.2833 0.3450 0.4829 11.00000 0.05 0.54 Q3 1 0.1568 0.3087 0.4190 11.00000 0.05 0.50 Q4 1 0.0545 0.6208 0.6342 11.00000 0.05 0.48 Q5 1 0.3798 0.3893 0.2638 11.00000 0.05 0.46 Q6 1 0.1530 0.4389 0.6577 11.00000 0.05 0.45 Q7 1 0.1367 0.2992 0.6721 11.00000 0.05 0.43 Q8 1 0.2845 0.4412 0.4818 11.00000 0.05 0.43 Q9 1 0.2171 0.2483 0.4863 11.00000 0.05 0.41 Q10 1 0.0411 0.5945 0.6250 11.00000 0.05 0.41 Q11 1 0.2446 0.2668 0.4968 11.00000 0.05 0.41 Q12 1 0.2544 0.2638 0.4251 11.00000 0.05 0.39 Q13 1 0.2795 0.1840 0.2330 11.00000 0.05 0.38 Q14 1 0.0216 0.3437 0.5734 11.00000 0.05 0.37 Q15 1 0.1843 0.4884 0.3990 11.00000 0.05 0.36 Q16 1 0.0641 0.2852 0.6414 11.00000 0.05 0.36 Q17 1 0.2212 0.5014 0.4150 11.00000 0.05 0.36 Q18 1 0.0216 0.4680 0.5529 11.00000 0.05 0.36 Q19 1 0.3625 0.6692 0.4401 11.00000 0.05 0.35 Q20 1 0.2566 0.2484 0.2248 11.00000 0.05 0.34 ; _shelx_res_checksum 95782 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.33706(9) 0.26952(18) 0.28741(10) 0.0444(4) Uani 1 1 d . . . . . O1 O 0.3680(3) 0.1301(5) 0.2525(3) 0.0714(16) Uani 1 1 d . . . . . N1 N 0.1751(3) 0.1556(5) 0.4850(3) 0.0347(12) Uani 1 1 d . . . . . C1 C 0.2020(4) 0.0582(7) 0.5468(4) 0.0442(16) Uani 1 1 d . . . . . H1 H 0.2440 0.0906 0.5829 0.053 Uiso 1 1 calc R U . . . Cu1 Cu 0.21307(4) 0.37217(8) 0.45663(5) 0.0378(3) Uani 1 1 d D . . . . O2 O 0.2940(3) 0.3539(8) 0.2246(4) 0.096(2) Uani 1 1 d . . . . . N2 N 0.1167(5) 0.3735(9) 0.3817(6) 0.037(3) Uani 0.644(18) 1 d D U P A 1 H2 H 0.0778 0.4259 0.4156 0.045 Uiso 0.644(18) 1 calc R U P A 1 C2 C 0.1704(4) -0.0878(7) 0.5594(5) 0.0496(18) Uani 1 1 d . . . . . H2A H 0.1913 -0.1548 0.6026 0.060 Uiso 1 1 calc R U . . . Cl2 Cl 0.08689(10) 0.42723(18) 0.62168(12) 0.0530(5) Uani 1 1 d D . . . . C3 C 0.1089(4) -0.1346(7) 0.5091(5) 0.0524(19) Uani 1 1 d . . . . . H3 H 0.0858 -0.2331 0.5175 0.063 Uiso 1 1 calc R U . . . N3 N 0.2275(3) 0.5817(5) 0.3981(3) 0.0365(12) Uani 1 1 d . . . . . O3 O 0.2877(3) 0.2292(5) 0.3540(3) 0.0764(18) Uani 1 1 d . . . . . C4 C 0.0814(4) -0.0352(7) 0.4458(4) 0.0425(16) Uani 1 1 d . . . . . H4 H 0.0388 -0.0649 0.4098 0.051 Uiso 1 1 calc R U . . . N5 N 0.3370(4) 0.7407(7) 0.6269(5) 0.0710(19) Uani 1 1 d . . . . . O4 O 0.3970(3) 0.3645(6) 0.3218(4) 0.0742(16) Uani 1 1 d . . . . . C5 C 0.1159(3) 0.1079(6) 0.4351(4) 0.0328(13) Uani 1 1 d . . . . . O5 O 0.1172(5) 0.4897(10) 0.5466(5) 0.078(3) Uani 0.755(8) 1 d D U P B 1 O6 O 0.0315(5) 0.3159(10) 0.5990(6) 0.091(3) Uani 0.755(8) 1 d D U P B 1 C6 C 0.0889(4) 0.2178(7) 0.3661(4) 0.0488(17) Uani 1 1 d D . . . . H6AA H 0.1063 0.1804 0.3112 0.059 Uiso 0.644(18) 1 calc R U P A 1 H6AB H 0.0326 0.2193 0.3622 0.059 Uiso 0.644(18) 1 calc R U P A 1 H6BC H 0.0754 0.1583 0.3137 0.059 Uiso 0.356(18) 1 calc R U P A 2 H6BD H 0.0427 0.2729 0.3831 0.059 Uiso 0.356(18) 1 calc R U P A 2 C7 C 0.1259(3) 0.4743(7) 0.3081(4) 0.0441(16) Uani 1 1 d D . . . . H7AA H 0.0758 0.5165 0.2879 0.053 Uiso 0.644(18) 1 calc R U P A 1 H7AB H 0.1464 0.4126 0.2616 0.053 Uiso 0.644(18) 1 calc R U P A 1 H7BC H 0.0740 0.5031 0.3232 0.053 Uiso 0.356(18) 1 calc R U P A 2 H7BD H 0.1247 0.4582 0.2460 0.053 Uiso 0.356(18) 1 calc R U P A 2 O7 O 0.0569(10) 0.5480(13) 0.6712(7) 0.077(3) Uani 0.755(8) 1 d D U P B 1 C8 C 0.1790(3) 0.6065(6) 0.3314(4) 0.0354(14) Uani 1 1 d . . . . . O8 O 0.1515(4) 0.3510(9) 0.6676(5) 0.076(2) Uani 0.755(8) 1 d D U P B 1 C9 C 0.1772(4) 0.7432(6) 0.2854(4) 0.0402(15) Uani 1 1 d . . . . . H9 H 0.1414 0.7570 0.2387 0.048 Uiso 1 1 calc R U . . . C10 C 0.2283(4) 0.8596(7) 0.3082(4) 0.0453(17) Uani 1 1 d . . . . . H10 H 0.2286 0.9547 0.2773 0.054 Uiso 1 1 calc R U . . . C11 C 0.2789(4) 0.8354(7) 0.3766(4) 0.0484(17) Uani 1 1 d . . . . . H11 H 0.3145 0.9144 0.3932 0.058 Uiso 1 1 calc R U . . . C12 C 0.2780(4) 0.6971(7) 0.4209(4) 0.0453(16) Uani 1 1 d . . . . . H12 H 0.3131 0.6818 0.4681 0.054 Uiso 1 1 calc R U . . . N4 N 0.2900(3) 0.4072(5) 0.5529(3) 0.0378(12) Uani 1 1 d . . . . . H4A H 0.2811 0.5037 0.5743 0.045 Uiso 1 1 calc R U . . . H4B H 0.2800 0.3372 0.5942 0.045 Uiso 1 1 calc R U . . . C13 C 0.3722(3) 0.3974(6) 0.5395(4) 0.0394(15) Uani 1 1 d . . . . . H13A H 0.4007 0.4546 0.5855 0.047 Uiso 1 1 calc R U . . . H13B H 0.3825 0.4490 0.4852 0.047 Uiso 1 1 calc R U . . . C14 C 0.4007(4) 0.2320(7) 0.5375(4) 0.0465(17) Uani 1 1 d . . . . . H14A H 0.3692 0.1720 0.4951 0.056 Uiso 1 1 calc R U . . . H14B H 0.3950 0.1834 0.5937 0.056 Uiso 1 1 calc R U . . . C15 C 0.4831(3) 0.2227(7) 0.5158(5) 0.0455(17) Uani 1 1 d . . . . . H15A H 0.4871 0.2572 0.4564 0.055 Uiso 1 1 calc R U . . . H15B H 0.5130 0.2964 0.5526 0.055 Uiso 1 1 calc R U . . . C16 C 0.5178(4) 0.0624(9) 0.5257(6) 0.071(2) Uani 1 1 d . . . . . H16A H 0.5718 0.0694 0.5120 0.085 Uiso 1 1 calc R U . . . H16B H 0.5167 0.0318 0.5861 0.085 Uiso 1 1 calc R U . . . C17 C 0.3813(4) 0.7615(7) 0.6812(5) 0.0508(18) Uani 1 1 d . . . . . C18 C 0.4373(4) 0.7811(9) 0.7485(5) 0.065(2) Uani 1 1 d . . . . . H18A H 0.4875 0.7909 0.7252 0.098 Uiso 1 1 calc R U . . . H18B H 0.4369 0.6904 0.7863 0.098 Uiso 1 1 calc R U . . . H18C H 0.4263 0.8757 0.7805 0.098 Uiso 1 1 calc R U . . . O7A O 0.057(3) 0.512(5) 0.691(2) 0.077(3) Uani 0.245(8) 1 d D U P B 2 O5A O 0.1451(13) 0.508(3) 0.585(2) 0.078(3) Uani 0.245(8) 1 d D U P B 2 O8A O 0.0991(15) 0.279(2) 0.6605(15) 0.076(2) Uani 0.245(8) 1 d D U P B 2 O6A O 0.0218(12) 0.403(3) 0.5629(16) 0.091(3) Uani 0.245(8) 1 d D U P B 2 N2A N 0.1473(8) 0.3302(15) 0.3499(9) 0.032(5) Uani 0.356(18) 1 d D U P A 2 H2AA H 0.1814 0.2764 0.3107 0.039 Uiso 0.356(18) 1 calc R U P A 2 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 Cl1 0.0579(10) 0.0457(9) 0.0300(9) 0.0015(7) 0.0064(8) -0.0069(8) O1 0.102(4) 0.050(3) 0.065(4) -0.016(3) 0.030(3) -0.003(3) N1 0.047(3) 0.029(3) 0.028(3) 0.003(2) 0.005(2) 0.006(2) C1 0.052(4) 0.039(4) 0.041(4) -0.003(3) 0.001(3) -0.003(3) Cu1 0.0461(5) 0.0286(4) 0.0382(5) 0.0056(3) -0.0021(3) -0.0047(3) O2 0.079(4) 0.160(6) 0.050(4) 0.019(4) 0.001(3) 0.047(4) N2 0.039(4) 0.032(4) 0.042(4) 0.006(3) 0.005(3) -0.002(3) C2 0.066(5) 0.035(4) 0.049(4) 0.015(3) 0.015(4) 0.008(3) Cl2 0.0627(11) 0.0333(8) 0.0641(12) -0.0098(8) 0.0130(10) -0.0064(8) C3 0.056(4) 0.030(3) 0.074(5) 0.004(4) 0.026(4) -0.003(3) N3 0.046(3) 0.030(3) 0.034(3) 0.000(2) 0.003(2) 0.001(2) O3 0.133(5) 0.049(3) 0.053(3) -0.009(2) 0.056(3) -0.032(3) C4 0.042(4) 0.034(3) 0.052(4) -0.006(3) 0.012(3) -0.006(3) N5 0.085(5) 0.067(4) 0.060(5) -0.019(4) 0.000(4) 0.017(4) O4 0.067(3) 0.070(4) 0.085(4) -0.019(3) 0.004(3) -0.022(3) C5 0.038(3) 0.028(3) 0.034(3) -0.001(3) 0.008(3) 0.003(3) O5 0.073(5) 0.062(4) 0.100(6) 0.027(4) 0.029(4) 0.017(4) O6 0.096(4) 0.072(5) 0.108(6) -0.025(4) 0.020(4) -0.041(4) C6 0.057(4) 0.039(4) 0.050(4) 0.005(3) -0.007(3) -0.009(3) C7 0.045(4) 0.042(4) 0.045(4) 0.015(3) -0.002(3) -0.006(3) O7 0.065(3) 0.064(6) 0.101(6) -0.039(5) -0.001(5) 0.011(4) C8 0.042(3) 0.031(3) 0.034(4) -0.001(3) 0.007(3) 0.006(3) O8 0.079(5) 0.076(4) 0.073(4) -0.007(4) 0.008(4) 0.020(4) C9 0.053(4) 0.034(3) 0.035(4) 0.004(3) 0.012(3) 0.007(3) C10 0.069(5) 0.022(3) 0.047(4) 0.007(3) 0.020(4) 0.009(3) C11 0.061(4) 0.032(3) 0.053(5) 0.003(3) 0.016(4) -0.007(3) C12 0.055(4) 0.037(3) 0.043(4) 0.000(3) 0.002(3) -0.006(3) N4 0.046(3) 0.034(3) 0.034(3) 0.000(2) 0.006(2) 0.001(2) C13 0.041(4) 0.034(3) 0.043(4) -0.002(3) 0.003(3) 0.003(3) C14 0.054(4) 0.044(4) 0.042(4) 0.000(3) 0.009(3) 0.002(3) C15 0.041(4) 0.036(3) 0.059(5) -0.008(3) 0.004(3) 0.007(3) C16 0.053(5) 0.063(5) 0.098(7) -0.021(5) 0.009(4) 0.008(4) C17 0.059(5) 0.041(4) 0.053(5) -0.004(3) 0.006(4) 0.009(3) C18 0.067(5) 0.068(5) 0.060(5) -0.007(4) 0.005(4) -0.001(4) O7A 0.065(3) 0.064(6) 0.101(6) -0.039(5) -0.001(5) 0.011(4) O5A 0.073(5) 0.062(4) 0.100(6) 0.027(4) 0.029(4) 0.017(4) O8A 0.079(5) 0.076(4) 0.073(4) -0.007(4) 0.008(4) 0.020(4) O6A 0.096(4) 0.072(5) 0.108(6) -0.025(4) 0.020(4) -0.041(4) N2A 0.034(6) 0.032(6) 0.031(6) -0.001(4) 0.005(4) -0.003(4) 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 O1 Cl1 O3 109.8(3) . . ? O2 Cl1 O1 110.8(4) . . ? O2 Cl1 O3 108.2(4) . . ? O2 Cl1 O4 109.5(4) . . ? O4 Cl1 O1 109.5(3) . . ? O4 Cl1 O3 109.0(3) . . ? C1 N1 Cu1 128.1(4) . . ? C5 N1 C1 118.0(5) . . ? C5 N1 Cu1 113.9(4) . . ? N1 C1 H1 118.9 . . ? N1 C1 C2 122.2(6) . . ? C2 C1 H1 118.9 . . ? N1 Cu1 N3 162.57(19) . . ? N2 Cu1 N1 81.8(2) . . ? N2 Cu1 N3 81.5(2) . . ? N4 Cu1 N1 100.79(19) . . ? N4 Cu1 N2 163.3(4) . . ? N4 Cu1 N3 96.6(2) . . ? N4 Cu1 N2A 172.3(5) . . ? N2A Cu1 N1 80.8(3) . . ? N2A Cu1 N3 81.9(3) . . ? Cu1 N2 H2 105.7 . . ? C6 N2 Cu1 111.3(5) . . ? C6 N2 H2 105.7 . . ? C6 N2 C7 117.6(7) . . ? C7 N2 Cu1 110.0(5) . . ? C7 N2 H2 105.7 . . ? C1 C2 H2A 120.2 . . ? C3 C2 C1 119.5(6) . . ? C3 C2 H2A 120.2 . . ? O5 Cl2 O8 105.1(5) . . ? O6 Cl2 O5 109.4(5) . . ? O6 Cl2 O7 111.3(8) . . ? O6 Cl2 O8 109.5(5) . . ? O7 Cl2 O5 110.6(6) . . ? O7 Cl2 O8 110.8(7) . . ? O7A Cl2 O6A 104(3) . . ? O5A Cl2 O7A 112(3) . . ? O5A Cl2 O8A 121.7(16) . . ? O5A Cl2 O6A 112.5(17) . . ? O8A Cl2 O7A 100(2) . . ? O8A Cl2 O6A 104.0(15) . . ? C2 C3 H3 120.8 . . ? C2 C3 C4 118.4(6) . . ? C4 C3 H3 120.8 . . ? C8 N3 Cu1 114.0(4) . . ? C8 N3 C12 118.1(5) . . ? C12 N3 Cu1 127.9(4) . . ? C3 C4 H4 120.1 . . ? C3 C4 C5 119.8(6) . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 122.2(6) . . ? N1 C5 C6 116.3(5) . . ? C4 C5 C6 121.5(6) . . ? N2 C6 C5 111.5(6) . . ? N2 C6 H6AA 109.3 . . ? N2 C6 H6AB 109.3 . . ? C5 C6 H6AA 109.3 . . ? C5 C6 H6AB 109.3 . . ? C5 C6 H6BC 109.6 . . ? C5 C6 H6BD 109.6 . . ? H6AA C6 H6AB 108.0 . . ? H6BC C6 H6BD 108.1 . . ? N2A C6 C5 110.3(6) . . ? N2A C6 H6BC 109.6 . . ? N2A C6 H6BD 109.6 . . ? N2 C7 H7AA 109.6 . . ? N2 C7 H7AB 109.6 . . ? N2 C7 C8 110.2(6) . . ? H7AA C7 H7AB 108.1 . . ? H7BC C7 H7BD 107.8 . . ? C8 C7 H7AA 109.6 . . ? C8 C7 H7AB 109.6 . . ? C8 C7 H7BC 109.0 . . ? C8 C7 H7BD 109.0 . . ? N2A C7 H7BC 109.0 . . ? N2A C7 H7BD 109.0 . . ? N2A C7 C8 113.0(6) . . ? N3 C8 C7 115.8(5) . . ? N3 C8 C9 123.1(6) . . ? C9 C8 C7 121.1(6) . . ? C8 C9 H9 120.6 . . ? C10 C9 C8 118.8(6) . . ? C10 C9 H9 120.6 . . ? C9 C10 H10 120.6 . . ? C11 C10 C9 118.7(6) . . ? C11 C10 H10 120.6 . . ? C10 C11 H11 119.9 . . ? C10 C11 C12 120.2(6) . . ? C12 C11 H11 119.9 . . ? N3 C12 C11 121.0(6) . . ? N3 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? Cu1 N4 H4A 107.2 . . ? Cu1 N4 H4B 107.2 . . ? H4A N4 H4B 106.8 . . ? C13 N4 Cu1 120.6(4) . . ? C13 N4 H4A 107.2 . . ? C13 N4 H4B 107.2 . . ? N4 C13 H13A 109.0 . . ? N4 C13 H13B 109.0 . . ? N4 C13 C14 112.8(5) . . ? H13A C13 H13B 107.8 . . ? C14 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C13 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C13 C14 C15 112.3(5) . . ? H14A C14 H14B 107.9 . . ? C15 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? C14 C15 H15A 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C16 C15 C14 114.4(6) . . ? C16 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C15 C16 H16A 108.1 . . ? C15 C16 H16B 108.1 . . ? C16 C16 C15 116.7(9) 3_656 . ? C16 C16 H16A 108.1 3_656 . ? C16 C16 H16B 108.1 3_656 . ? H16A C16 H16B 107.3 . . ? N5 C17 C18 177.7(7) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? Cu1 N2A H2AA 105.2 . . ? C6 N2A Cu1 110.6(8) . . ? C6 N2A H2AA 105.2 . . ? C7 N2A Cu1 110.6(7) . . ? C7 N2A C6 118.8(10) . . ? C7 N2A H2AA 105.2 . . ? 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 Cl1 O1 1.436(5) . ? Cl1 O2 1.414(6) . ? Cl1 O3 1.444(4) . ? Cl1 O4 1.417(5) . ? N1 C1 1.350(8) . ? N1 Cu1 2.031(5) . ? N1 C5 1.335(7) . ? C1 H1 0.9500 . ? C1 C2 1.388(8) . ? Cu1 N2 2.014(7) . ? Cu1 N3 2.041(5) . ? Cu1 N4 2.003(5) . ? Cu1 N2A 2.023(11) . ? N2 H2 1.0000 . ? N2 C6 1.438(9) . ? N2 C7 1.464(9) . ? C2 H2A 0.9500 . ? C2 C3 1.367(10) . ? Cl2 O5 1.432(7) . ? Cl2 O6 1.397(7) . ? Cl2 O7 1.417(7) . ? Cl2 O8 1.468(7) . ? Cl2 O7A 1.443(17) . ? Cl2 O5A 1.388(16) . ? Cl2 O8A 1.424(16) . ? Cl2 O6A 1.450(17) . ? C3 H3 0.9500 . ? C3 C4 1.380(9) . ? N3 C8 1.337(7) . ? N3 C12 1.365(7) . ? C4 H4 0.9500 . ? C4 C5 1.384(8) . ? N5 C17 1.140(9) . ? C5 C6 1.497(8) . ? C6 H6AA 0.9900 . ? C6 H6AB 0.9900 . ? C6 H6BC 0.9900 . ? C6 H6BD 0.9900 . ? C6 N2A 1.443(12) . ? C7 H7AA 0.9900 . ? C7 H7AB 0.9900 . ? C7 H7BC 0.9900 . ? C7 H7BD 0.9900 . ? C7 C8 1.501(8) . ? C7 N2A 1.440(12) . ? C8 C9 1.378(8) . ? C9 H9 0.9500 . ? C9 C10 1.378(8) . ? C10 H10 0.9500 . ? C10 C11 1.377(9) . ? C11 H11 0.9500 . ? C11 C12 1.377(8) . ? C12 H12 0.9500 . ? N4 H4A 0.9100 . ? N4 H4B 0.9100 . ? N4 C13 1.480(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C14 1.503(8) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C15 1.513(8) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15 C16 1.509(9) . ? C16 C16 1.462(14) 3_656 ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.421(10) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 N1 C1 C2 C3 -1.4(10) . . . . ? N1 C5 C6 N2 -17.5(9) . . . . ? N1 C5 C6 N2A 19.0(11) . . . . ? C1 N1 C5 C4 1.0(8) . . . . ? C1 N1 C5 C6 -178.7(5) . . . . ? C1 C2 C3 C4 1.4(10) . . . . ? Cu1 N1 C1 C2 179.9(5) . . . . ? Cu1 N1 C5 C4 -178.7(4) . . . . ? Cu1 N1 C5 C6 1.5(6) . . . . ? Cu1 N2 C6 C5 24.6(9) . . . . ? Cu1 N2 C7 C8 -31.6(8) . . . . ? Cu1 N3 C8 C7 -3.3(6) . . . . ? Cu1 N3 C8 C9 177.2(5) . . . . ? Cu1 N3 C12 C11 -177.5(4) . . . . ? Cu1 N4 C13 C14 -79.7(6) . . . . ? N2 C7 C8 N3 23.2(8) . . . . ? N2 C7 C8 C9 -157.3(7) . . . . ? C2 C3 C4 C5 -0.2(9) . . . . ? C3 C4 C5 N1 -1.0(9) . . . . ? C3 C4 C5 C6 178.7(6) . . . . ? N3 C8 C9 C10 0.9(9) . . . . ? C4 C5 C6 N2 162.8(7) . . . . ? C4 C5 C6 N2A -160.7(9) . . . . ? C5 N1 C1 C2 0.2(9) . . . . ? C5 C6 N2A Cu1 -30.0(12) . . . . ? C5 C6 N2A C7 -159.5(10) . . . . ? C6 N2 C7 C8 -160.4(7) . . . . ? C7 N2 C6 C5 152.8(7) . . . . ? C7 C8 C9 C10 -178.6(6) . . . . ? C8 N3 C12 C11 0.2(9) . . . . ? C8 C7 N2A Cu1 22.5(12) . . . . ? C8 C7 N2A C6 152.1(10) . . . . ? C8 C9 C10 C11 -0.5(9) . . . . ? C9 C10 C11 C12 0.0(9) . . . . ? C10 C11 C12 N3 0.2(10) . . . . ? C12 N3 C8 C7 178.8(5) . . . . ? C12 N3 C8 C9 -0.7(8) . . . . ? N4 C13 C14 C15 174.8(5) . . . . ? C13 C14 C15 C16 171.3(6) . . . . ? C14 C15 C16 C16 59.9(12) . . . 3_656 ? N2A C7 C8 N3 -13.0(11) . . . . ? N2A C7 C8 C9 166.5(9) . . . . ?