#------------------------------------------------------------------------------ #$Date: 2018-01-17 07:26:35 +0200 (Wed, 17 Jan 2018) $ #$Revision: 205299 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229991.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_7229991 loop_ _publ_author_name 'Yepremyan, Akop' 'Mehmood, Arshad' 'Brewer, Samantha M.' 'Barnett, Madalyn M.' 'Janesko, Benjamin G.' 'Akkaraju, Giridhar' 'Simanek, Eric E.' 'Green, Kayla N.' _publ_section_title ; A new triazine bearing a pyrazolone group capable of copper, nickel, and zinc chelation ; _journal_issue 6 _journal_name_full 'RSC Advances' _journal_page_first 3024 _journal_paper_doi 10.1039/C7RA09459K _journal_volume 8 _journal_year 2018 _chemical_formula_moiety 'C11 H17 Cl Cu N8 O3, C11 H16 Cl2 Cu N8 O2, 3(H2 O), 0.5(O2)' _chemical_formula_sum 'C22 H39 Cl3 Cu2 N16 O9' _chemical_formula_weight 905.14 _chemical_melting_point ? _chemical_name_common none _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary mixed _audit_creation_date 2017-08-06 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-06-09 deposited with the CCDC. 2018-01-02 downloaded from the CCDC. ; _cell_angle_alpha 97.586(2) _cell_angle_beta 103.997(2) _cell_angle_gamma 106.156(2) _cell_formula_units_Z 2 _cell_length_a 11.3979(6) _cell_length_b 12.0551(7) _cell_length_c 13.6836(7) _cell_measurement_reflns_used 9886 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.82 _cell_measurement_theta_min 2.96 _cell_volume 1711.75(16) _computing_cell_refinement 'Apex3 (Bruker AXS Inc., 2016)' _computing_data_collection 'Apex3 (Bruker AXS Inc., 2016)' _computing_data_reduction 'SAINT V8.32B (Bruker AXS Inc., 2013)' _computing_molecular_graphics ; ORTEp-3 (Farrugia, 2012) and Olex2 (Dolomanov et al., 2009) ; _computing_publication_material 'WinGX2014.1 (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT (Sheldrick, 2013)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'Photon 100 CMOS detector' _diffrn_detector_area_resol_mean 10.24 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type ; Bruker D8 Quest with Photon 100 CMOS Detector ; _diffrn_measurement_method ; \f and \w scans with 0.5 deg/frame and 20 seconds of exposure time. Detector was at 45mm from crystal. ; _diffrn_radiation_monochromator 'Multi-layer X-ray mirror' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_unetI/netI 0.0325 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 86344 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 27.185 _diffrn_reflns_theta_min 2.959 _diffrn_source 'fine-focused sealed tube' _exptl_absorpt_coefficient_mu 1.551 _exptl_absorpt_correction_T_max 0.933 _exptl_absorpt_correction_T_min 0.876 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0675 before and 0.0632 after correction. The Ratio of minimum to maximum transmission is 0.9303. The \l/2 correction factor is 0.00150. ; _exptl_crystal_colour Blue _exptl_crystal_density_diffrn 1.756 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description Needle _exptl_crystal_F_000 928 _exptl_crystal_size_max 0.226 _exptl_crystal_size_mid 0.071 _exptl_crystal_size_min 0.045 _exptl_transmission_factor_max 0.972 _exptl_transmission_factor_min 0.956 _refine_diff_density_max 2.201 _refine_diff_density_min -1.005 _refine_diff_density_rms 0.097 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 535 _refine_ls_number_reflns 7595 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0386 _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^)+(0.0320P)^2^+4.0982P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0815 _refine_ls_wR_factor_ref 0.0886 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6122 _reflns_number_total 7595 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra09459k5.cif _cod_data_source_block Complex-6 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value 'not measured' was changed to '?' - the value is undefined or not given. '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 7229991 _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. ; _exptl_absorpt_special_details ; The crystal was mounted using Paratone-N oil (cryoprotectant) on the tip of MiTeGen MicroLoops LD?. It was placed on magnetic head of goniometer directly into the cold gas stream of a liquid-nitrogen based cryostat. ; _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL AMakop10_0m_a.res in P-1 REM Old TITL AMakop10_0m in P-1 REM SHELXT solution in P-1 REM R1 0.106, Rweak 0.007, Alpha 0.058, Orientation as input REM Formula found by SHELXT: C35 O1 Cu1 H6b Cl2 CELL 0.71073 11.3979 12.0551 13.6836 97.586 103.997 106.156 ZERR 4 0.0006 0.0007 0.0007 0.002 0.002 0.002 LATT 1 SFAC C H Cl Cu N O UNIT 44 78 6 4 32 18 EQIV $1 1-X,1-Y,1-Z EQIV $2 -X,1-Y,1-Z EQIV $3 -1+X,+Y,+Z EQIV $4 1+X,1+Y,+Z EQIV $5 -X,1-Y,2-Z EQIV $6 1-X,1-Y,2-Z EADP O8A O8B L.S. 50 PLAN 30 TEMP -173.15 HTAB O3 N8_$1 HTAB O3 Cl2_$2 HTAB N5 O7_$3 HTAB N6 Cl2 HTAB N6 Cl1_$2 HTAB N13 O8A HTAB N13 O8B HTAB N14 Cl3_$5 HTAB N14 Cl1 HTAB O6 O2_$4 HTAB O6 O1 HTAB O7 Cl1_$1 HTAB O7 O6 HTAB O8A Cl2_$5 HTAB O8B Cl2_$5 HTAB O8A Cl3_$5 HTAB O8B Cl3_$5 HTAB N16 Cl3_$6 BOND $H LIST 4 HTAB fmap 2 acta 50 REM REM REM WGHT 0.032000 4.098200 FVAR 0.21880 0.32045 PART 1 O8A 6 -0.104788 0.148594 0.963748 21.00000 0.02616 0.01665 = 0.02796 0.00615 0.01275 0.00929 PART 0 PART 2 O8B 6 -0.130108 0.181802 0.964297 -21.00000 0.02616 0.01665 = 0.02796 0.00615 0.01275 0.00929 PART 0 CU1 4 0.211697 0.482089 0.603003 11.00000 0.00638 0.01121 = 0.01214 0.00312 0.00267 0.00150 CL1 3 0.019839 0.370105 0.613410 11.00000 0.00845 0.01981 = 0.01494 0.00664 0.00365 0.00148 O1 6 0.936039 1.027613 0.695618 11.00000 0.01056 0.01289 = 0.03876 0.00274 0.00595 0.00170 O2 6 0.282423 0.359547 0.631537 11.00000 0.00901 0.01348 = 0.01962 0.00670 0.00618 0.00259 O3 6 0.174318 0.453076 0.426754 11.00000 0.00935 0.01967 = 0.01476 0.00356 0.00442 0.00283 H3A 2 0.227215 0.475617 0.410952 11.00000 0.01628 H3B 2 0.122724 0.450146 0.383671 11.00000 0.03582 N1 5 0.698016 0.846619 0.625721 11.00000 0.01020 0.00933 = 0.01955 0.00256 0.00617 0.00157 N2 5 0.483222 0.793281 0.613799 11.00000 0.01106 0.00971 = 0.01321 0.00177 0.00283 0.00233 N3 5 0.596519 0.651673 0.619235 11.00000 0.00930 0.01083 = 0.01034 0.00211 0.00287 0.00236 N4 5 0.379424 0.593168 0.617025 11.00000 0.00866 0.01176 = 0.01022 0.00209 0.00245 0.00258 N5 5 0.271734 0.726632 0.606877 11.00000 0.01006 0.01006 = 0.01959 0.00431 0.00512 0.00310 H5 2 0.259513 0.787136 0.602093 11.00000 0.01238 N6 5 0.164547 0.631680 0.606509 11.00000 0.00799 0.01497 = 0.01158 0.00291 0.00325 0.00178 H6A 2 0.146037 0.652468 0.660900 11.00000 0.01746 H6B 2 0.098563 0.621980 0.548345 11.00000 0.02219 N7 5 0.492448 0.460324 0.624776 11.00000 0.00757 0.01078 = 0.01276 0.00234 0.00349 0.00149 N8 5 0.605558 0.434554 0.628784 11.00000 0.00828 0.01436 = 0.01433 0.00236 0.00388 0.00499 C1 1 0.822322 1.052038 0.702985 11.00000 0.01353 0.01339 = 0.03385 -0.00224 0.00479 0.00285 AFIX 23 H1A 2 0.830762 1.134350 0.695894 11.00000 -1.20000 H1B 2 0.811961 1.045028 0.771915 11.00000 -1.20000 AFIX 0 C2 1 0.704182 0.968186 0.620628 11.00000 0.01316 0.01157 = 0.02472 0.00493 0.00594 0.00208 AFIX 23 H2A 2 0.626645 0.982531 0.632050 11.00000 -1.20000 H2B 2 0.708344 0.981976 0.551627 11.00000 -1.20000 AFIX 0 C3 1 0.927426 0.909248 0.705286 11.00000 0.01210 0.01609 = 0.02550 0.00550 0.00486 0.00398 AFIX 23 H3C 2 0.917112 0.898612 0.773585 11.00000 -1.20000 H3D 2 1.007350 0.894556 0.700640 11.00000 -1.20000 AFIX 0 C4 1 0.815437 0.821454 0.621440 11.00000 0.01108 0.01164 = 0.02562 0.00186 0.00914 0.00231 AFIX 23 H4A 2 0.828773 0.827260 0.553194 11.00000 -1.20000 H4B 2 0.808194 0.740115 0.631082 11.00000 -1.20000 AFIX 0 C5 1 0.589120 0.762384 0.618818 11.00000 0.01204 0.01404 = 0.00567 0.00059 0.00166 0.00336 C6 1 0.490385 0.573027 0.619769 11.00000 0.00952 0.01323 = 0.00497 0.00044 0.00075 0.00256 C7 1 0.382338 0.705436 0.612686 11.00000 0.01026 0.01372 = 0.00584 0.00014 0.00128 0.00323 C8 1 0.396498 0.361311 0.631647 11.00000 0.01053 0.01301 = 0.00902 0.00262 0.00139 0.00050 C9 1 0.451681 0.273876 0.640334 11.00000 0.01305 0.01256 = 0.01530 0.00495 0.00497 0.00436 AFIX 43 H9 2 0.412327 0.195562 0.646410 11.00000 -1.20000 AFIX 0 C10 1 0.578142 0.323526 0.638433 11.00000 0.01376 0.01310 = 0.01053 0.00397 0.00336 0.00513 C11 1 0.677994 0.264726 0.647346 11.00000 0.01564 0.01634 = 0.02275 0.00539 0.00716 0.00885 AFIX 137 H11A 2 0.752981 0.315767 0.633580 11.00000 -1.50000 H11B 2 0.644204 0.189202 0.597180 11.00000 -1.50000 H11C 2 0.702514 0.250508 0.717143 11.00000 -1.50000 AFIX 0 CU2 4 0.169896 0.540841 0.863073 11.00000 0.00749 0.01105 = 0.01516 0.00520 0.00545 0.00491 CL2 3 0.047456 0.653735 0.807893 11.00000 0.01196 0.01668 = 0.01829 0.00640 0.00597 0.00879 CL3 3 0.221677 0.594546 1.060323 11.00000 0.01030 0.01803 = 0.01404 0.00345 0.00498 0.00581 O4 6 0.450314 -0.062169 0.848753 11.00000 0.02352 0.01262 = 0.02712 0.00538 0.00971 0.01141 O5 6 0.321799 0.649794 0.846793 11.00000 0.00909 0.01247 = 0.01942 0.00708 0.00696 0.00657 N9 5 0.376379 0.139028 0.892426 11.00000 0.00924 0.00770 = 0.01869 0.00353 0.00386 0.00293 N10 5 0.210059 0.215105 0.884590 11.00000 0.00938 0.01006 = 0.01293 0.00114 0.00266 0.00266 N11 5 0.247927 0.414866 0.864332 11.00000 0.00726 0.01073 = 0.01194 0.00230 0.00238 0.00331 N12 5 0.418039 0.334608 0.883932 11.00000 0.01016 0.00853 = 0.01217 0.00257 0.00370 0.00370 N13 5 0.052115 0.301535 0.866509 11.00000 0.00825 0.00908 = 0.02059 0.00534 0.00595 0.00305 H13 2 0.006222 0.249434 0.887917 11.00000 0.01122 N14 5 0.015684 0.402750 0.851275 11.00000 0.00914 0.01521 = 0.01534 0.00425 0.00635 0.00665 H14A 2 -0.030176 0.413693 0.890755 11.00000 0.01689 H14B 2 -0.032494 0.387043 0.786642 11.00000 0.03216 N15 5 0.450582 0.526943 0.869147 11.00000 0.00720 0.01200 = 0.01409 0.00422 0.00522 0.00569 N16 5 0.576615 0.539933 0.875592 11.00000 0.00621 0.01396 = 0.01594 0.00400 0.00442 0.00600 C12 1 0.519543 0.048623 0.832881 11.00000 0.02523 0.01775 = 0.02805 0.01001 0.01521 0.01288 AFIX 23 H12A 2 0.484717 0.054226 0.760719 11.00000 -1.20000 H12B 2 0.610240 0.053882 0.844214 11.00000 -1.20000 AFIX 0 C13 1 0.318163 -0.073206 0.829514 11.00000 0.02135 0.01280 = 0.02505 0.00204 0.00132 0.00697 AFIX 23 H13A 2 0.271078 -0.151393 0.839220 11.00000 -1.20000 H13B 2 0.282682 -0.068856 0.757088 11.00000 -1.20000 AFIX 0 C14 1 0.511092 0.150285 0.905236 11.00000 0.00987 0.01406 = 0.02802 0.00649 0.00579 0.00721 AFIX 23 H14C 2 0.553346 0.149682 0.977368 11.00000 -1.20000 H14D 2 0.555411 0.226177 0.889973 11.00000 -1.20000 AFIX 0 C15 1 0.298794 0.023243 0.900964 11.00000 0.01415 0.01024 = 0.02658 0.00592 0.00705 0.00392 AFIX 23 H15A 2 0.207479 0.017530 0.881996 11.00000 -1.20000 H15B 2 0.324264 0.013498 0.972972 11.00000 -1.20000 AFIX 0 C16 1 0.333196 0.230290 0.887021 11.00000 0.00969 0.01083 = 0.00725 -0.00034 0.00023 0.00274 C17 1 0.173190 0.308797 0.872106 11.00000 0.00912 0.01145 = 0.00622 0.00009 0.00232 0.00256 C18 1 0.368278 0.418642 0.872371 11.00000 0.00956 0.01050 = 0.00681 0.00096 0.00347 0.00300 C19 1 0.429672 0.634129 0.857813 11.00000 0.01276 0.00977 = 0.00781 0.00328 0.00434 0.00506 C20 1 0.547655 0.711335 0.858410 11.00000 0.01049 0.01152 = 0.01093 0.00337 0.00370 0.00337 AFIX 43 H20 2 0.564888 0.791718 0.853093 11.00000 -1.20000 AFIX 0 C21 1 0.634107 0.650180 0.868053 11.00000 0.01091 0.01108 = 0.00873 0.00099 0.00330 0.00184 C22 1 0.769494 0.687371 0.866755 11.00000 0.00844 0.01741 = 0.01683 0.00619 0.00327 0.00190 AFIX 137 H22A 2 0.815245 0.642296 0.906420 11.00000 -1.50000 H22B 2 0.809829 0.771940 0.897569 11.00000 -1.50000 H22C 2 0.772600 0.672376 0.795421 11.00000 -1.50000 AFIX 0 O6 6 1.139940 1.122246 0.621338 11.00000 0.06626 0.01535 = 0.07171 0.00574 0.05787 0.00213 H6C 2 1.173755 1.189587 0.629411 11.00000 0.03007 H6D 2 1.089630 1.114244 0.640753 11.00000 0.04767 O7 6 1.153008 0.898397 0.556748 11.00000 0.02628 0.01902 = 0.02517 0.00385 0.00141 0.00956 H7A 2 1.090909 0.873132 0.512780 11.00000 0.03957 H7B 2 1.156899 0.959536 0.567827 11.00000 0.05474 H8AA 2 -0.099579 0.198510 1.017788 11.00000 0.04146 H8AB 2 -0.158022 0.213795 0.955374 11.00000 0.04922 O10 6 0.036062 0.040431 0.965208 11.00000 0.33138 0.25403 = 0.22171 0.08717 0.13439 0.02395 H16 2 0.609243 0.488280 0.884663 11.00000 0.02234 HKLF 4 REM AMakop10_0m_a.res in P-1 REM R1 = 0.0386 for 6122 Fo > 4sig(Fo) and 0.0565 for all 7595 data REM 535 parameters refined using 0 restraints END WGHT 0.0320 4.0984 REM Instructions for potential hydrogen bonds HTAB O3 N8_$1 HTAB O3 Cl2_$2 HTAB N5 O7_$3 HTAB N6 Cl2 HTAB N6 Cl1_$2 HTAB C1 O8A_$4 EQIV $7 -x+2, -y+2, -z+1 HTAB C4 O6_$7 HTAB C4 O3_$1 HTAB N13 O8A HTAB N13 O8B HTAB N14 Cl3_$5 HTAB N14 Cl1 EQIV $8 x, y-1, z HTAB C13 Cl2_$8 HTAB C13 O5_$8 HTAB C14 Cl3_$6 HTAB C15 O10 EQIV $9 x, y+1, z HTAB C20 O4_$9 HTAB C22 Cl3_$6 HTAB C22 O10_$6 HTAB C22 N3 HTAB O6 O2_$4 HTAB O6 O1 HTAB O7 Cl1_$1 HTAB O7 O6 HTAB O8A Cl2_$5 HTAB O8B Cl2_$5 HTAB O8A Cl3_$5 HTAB O8B Cl3_$5 HTAB N16 Cl3_$6 REM Highest difference peak 2.201, deepest hole -1.005, 1-sigma level 0.097 Q1 1 0.6454 0.4260 0.8982 11.00000 0.05 0.45 Q2 1 0.5800 0.7015 0.6108 11.00000 0.05 0.44 Q3 1 0.5183 0.2960 0.6505 11.00000 0.05 0.44 Q4 1 0.4013 0.4652 0.8561 11.00000 0.05 0.42 Q5 1 0.3282 0.0768 0.8853 11.00000 0.05 0.42 Q6 1 0.4183 0.5799 0.6046 11.00000 0.05 0.41 Q7 1 0.3882 0.6397 0.6144 11.00000 0.05 0.39 Q8 1 0.3074 0.4178 0.8749 11.00000 0.05 0.38 Q9 1 0.4402 0.4133 0.6294 11.00000 0.05 0.38 Q10 1 0.5969 0.6884 0.8754 11.00000 0.05 0.38 Q11 1 -0.0128 0.3606 0.5367 11.00000 0.05 0.37 Q12 1 0.5024 0.5095 0.6419 11.00000 0.05 0.36 Q13 1 0.4806 0.3622 0.9034 11.00000 0.05 0.36 Q14 1 0.2172 0.3590 0.8569 11.00000 0.05 0.35 Q15 1 -0.0625 0.1193 1.0059 11.00000 0.05 0.35 Q16 1 0.3985 0.2992 0.6175 11.00000 0.05 0.35 Q17 1 0.5263 0.5310 0.8820 11.00000 0.05 0.35 Q18 1 0.9922 0.9031 0.7602 11.00000 0.05 0.34 Q19 1 0.2863 0.4154 0.6317 11.00000 0.05 0.34 Q20 1 0.8239 0.7351 0.9177 11.00000 0.05 0.34 Q21 1 0.5594 0.7509 0.8758 11.00000 0.05 0.34 Q22 1 0.7548 1.0033 0.6612 11.00000 0.05 0.33 Q23 1 0.4982 0.6848 0.8681 11.00000 0.05 0.33 Q24 1 0.2442 0.2015 0.8606 11.00000 0.05 0.33 Q25 1 0.7525 0.8351 0.6351 11.00000 0.05 0.32 Q26 1 0.7927 0.7869 0.8496 11.00000 0.05 0.32 Q27 1 0.3457 0.3648 0.6373 11.00000 0.05 0.32 Q28 1 0.1111 0.1161 0.9541 11.00000 0.05 0.32 Q29 1 0.1634 0.2229 0.8497 11.00000 0.05 0.31 Q30 1 0.6197 0.2860 0.6467 11.00000 0.05 0.31 ; _shelx_res_checksum 84755 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 O8A O -0.1048(13) 0.1486(12) 0.9637(11) 0.0220(13) Uani 0.320(13) 1 d . . P A 1 O8B O -0.1301(6) 0.1818(6) 0.9643(4) 0.0220(13) Uani 0.680(13) 1 d . . P A 2 Cu1 Cu 0.21170(3) 0.48209(3) 0.60300(3) 0.01014(9) Uani 1 1 d . . . . . Cl1 Cl 0.01984(6) 0.37010(6) 0.61341(5) 0.01473(15) Uani 1 1 d . . . . . O1 O 0.93604(19) 1.02761(18) 0.69562(18) 0.0217(5) Uani 1 1 d . . . . . O2 O 0.28242(18) 0.35955(17) 0.63154(16) 0.0136(4) Uani 1 1 d . . . . . O3 O 0.1743(3) 0.4531(2) 0.42675(18) 0.0148(4) Uani 1 1 d . . . . . H3A H 0.227(4) 0.476(3) 0.411(3) 0.016(11) Uiso 1 1 d . . . . . H3B H 0.123(4) 0.450(4) 0.384(3) 0.036(14) Uiso 1 1 d . . . . . N1 N 0.6980(2) 0.8466(2) 0.62572(19) 0.0131(5) Uani 1 1 d . . . . . N2 N 0.4832(2) 0.7933(2) 0.61380(18) 0.0117(5) Uani 1 1 d . . . . . N3 N 0.5965(2) 0.6517(2) 0.61923(17) 0.0104(5) Uani 1 1 d . . . . . N4 N 0.3794(2) 0.5932(2) 0.61703(17) 0.0104(5) Uani 1 1 d . . . . . N5 N 0.2717(2) 0.7266(2) 0.60688(19) 0.0130(5) Uani 1 1 d . . . . . H5 H 0.260(3) 0.787(3) 0.602(3) 0.012(9) Uiso 1 1 d . . . . . N6 N 0.1645(2) 0.6317(2) 0.6065(2) 0.0118(5) Uani 1 1 d . . . . . H6A H 0.146(3) 0.652(3) 0.661(3) 0.017(9) Uiso 1 1 d . . . . . H6B H 0.099(3) 0.622(3) 0.548(3) 0.022(9) Uiso 1 1 d . . . . . N7 N 0.4924(2) 0.4603(2) 0.62478(18) 0.0106(5) Uani 1 1 d . . . . . N8 N 0.6056(2) 0.4346(2) 0.62878(18) 0.0120(5) Uani 1 1 d . . . . . C1 C 0.8223(3) 1.0520(3) 0.7030(3) 0.0217(7) Uani 1 1 d . . . . . H1A H 0.8308 1.1343 0.6959 0.026 Uiso 1 1 calc R U . . . H1B H 0.8120 1.0450 0.7719 0.026 Uiso 1 1 calc R U . . . C2 C 0.7042(3) 0.9682(2) 0.6206(2) 0.0167(6) Uani 1 1 d . . . . . H2A H 0.6266 0.9825 0.6321 0.020 Uiso 1 1 calc R U . . . H2B H 0.7083 0.9820 0.5516 0.020 Uiso 1 1 calc R U . . . C3 C 0.9274(3) 0.9092(3) 0.7053(2) 0.0180(6) Uani 1 1 d . . . . . H3C H 0.9171 0.8986 0.7736 0.022 Uiso 1 1 calc R U . . . H3D H 1.0073 0.8946 0.7006 0.022 Uiso 1 1 calc R U . . . C4 C 0.8154(3) 0.8215(3) 0.6214(2) 0.0159(6) Uani 1 1 d . . . . . H4A H 0.8288 0.8273 0.5532 0.019 Uiso 1 1 calc R U . . . H4B H 0.8082 0.7401 0.6311 0.019 Uiso 1 1 calc R U . . . C5 C 0.5891(3) 0.7624(2) 0.6188(2) 0.0111(5) Uani 1 1 d . . . . . C6 C 0.4904(3) 0.5730(2) 0.6198(2) 0.0099(5) Uani 1 1 d . . . . . C7 C 0.3823(3) 0.7054(2) 0.6127(2) 0.0105(5) Uani 1 1 d . . . . . C8 C 0.3965(3) 0.3613(2) 0.6316(2) 0.0118(6) Uani 1 1 d . . . . . C9 C 0.4517(3) 0.2739(3) 0.6403(2) 0.0132(6) Uani 1 1 d . . . . . H9 H 0.4123 0.1956 0.6464 0.016 Uiso 1 1 calc R U . . . C10 C 0.5781(3) 0.3235(2) 0.6384(2) 0.0122(6) Uani 1 1 d . . . . . C11 C 0.6780(3) 0.2647(3) 0.6473(2) 0.0170(6) Uani 1 1 d . . . . . H11A H 0.7530 0.3158 0.6336 0.026 Uiso 1 1 calc R U . . . H11B H 0.6442 0.1892 0.5972 0.026 Uiso 1 1 calc R U . . . H11C H 0.7025 0.2505 0.7171 0.026 Uiso 1 1 calc R U . . . Cu2 Cu 0.16990(3) 0.54084(3) 0.86307(3) 0.01019(9) Uani 1 1 d . . . . . Cl2 Cl 0.04746(6) 0.65374(6) 0.80789(5) 0.01419(15) Uani 1 1 d . . . . . Cl3 Cl 0.22168(6) 0.59455(6) 1.06032(5) 0.01359(14) Uani 1 1 d . . . . . O4 O 0.4503(2) -0.06217(18) 0.84875(17) 0.0193(5) Uani 1 1 d . . . . . O5 O 0.32180(18) 0.64979(17) 0.84679(15) 0.0121(4) Uani 1 1 d . . . . . N9 N 0.3764(2) 0.1390(2) 0.89243(19) 0.0118(5) Uani 1 1 d . . . . . N10 N 0.2101(2) 0.2151(2) 0.88459(18) 0.0111(5) Uani 1 1 d . . . . . N11 N 0.2479(2) 0.4149(2) 0.86433(18) 0.0100(5) Uani 1 1 d . . . . . N12 N 0.4180(2) 0.3346(2) 0.88393(18) 0.0100(5) Uani 1 1 d . . . . . N13 N 0.0521(2) 0.3015(2) 0.86651(19) 0.0120(5) Uani 1 1 d . . . . . H13 H 0.006(3) 0.249(3) 0.888(2) 0.011(8) Uiso 1 1 d . . . . . N14 N 0.0157(2) 0.4027(2) 0.8513(2) 0.0120(5) Uani 1 1 d . . . . . H14A H -0.030(3) 0.414(3) 0.891(3) 0.017(9) Uiso 1 1 d . . . . . H14B H -0.032(4) 0.387(3) 0.787(3) 0.032(11) Uiso 1 1 d . . . . . N15 N 0.4506(2) 0.5269(2) 0.86915(18) 0.0100(5) Uani 1 1 d . . . . . N16 N 0.5766(2) 0.5399(2) 0.87559(18) 0.0111(5) Uani 1 1 d . . . . . C12 C 0.5195(3) 0.0486(3) 0.8329(3) 0.0205(7) Uani 1 1 d . . . . . H12A H 0.4847 0.0542 0.7607 0.025 Uiso 1 1 calc R U . . . H12B H 0.6102 0.0539 0.8442 0.025 Uiso 1 1 calc R U . . . C13 C 0.3182(3) -0.0732(3) 0.8295(3) 0.0206(7) Uani 1 1 d . . . . . H13A H 0.2711 -0.1514 0.8392 0.025 Uiso 1 1 calc R U . . . H13B H 0.2827 -0.0689 0.7571 0.025 Uiso 1 1 calc R U . . . C14 C 0.5111(3) 0.1503(3) 0.9052(2) 0.0164(6) Uani 1 1 d . . . . . H14C H 0.5533 0.1497 0.9774 0.020 Uiso 1 1 calc R U . . . H14D H 0.5554 0.2262 0.8900 0.020 Uiso 1 1 calc R U . . . C15 C 0.2988(3) 0.0232(2) 0.9010(2) 0.0166(6) Uani 1 1 d . . . . . H15A H 0.2075 0.0175 0.8820 0.020 Uiso 1 1 calc R U . . . H15B H 0.3243 0.0135 0.9730 0.020 Uiso 1 1 calc R U . . . C16 C 0.3332(3) 0.2303(2) 0.8870(2) 0.0100(5) Uani 1 1 d . . . . . C17 C 0.1732(2) 0.3088(2) 0.8721(2) 0.0093(5) Uani 1 1 d . . . . . C18 C 0.3683(3) 0.4186(2) 0.8724(2) 0.0089(5) Uani 1 1 d . . . . . C19 C 0.4297(3) 0.6341(2) 0.8578(2) 0.0094(5) Uani 1 1 d . . . . . C20 C 0.5477(3) 0.7113(2) 0.8584(2) 0.0108(5) Uani 1 1 d . . . . . H20 H 0.5649 0.7917 0.8531 0.013 Uiso 1 1 calc R U . . . C21 C 0.6341(3) 0.6502(2) 0.8681(2) 0.0106(5) Uani 1 1 d . . . . . C22 C 0.7695(3) 0.6874(3) 0.8668(2) 0.0145(6) Uani 1 1 d . . . . . H22A H 0.8152 0.6423 0.9064 0.022 Uiso 1 1 calc R U . . . H22B H 0.8098 0.7719 0.8976 0.022 Uiso 1 1 calc R U . . . H22C H 0.7726 0.6724 0.7954 0.022 Uiso 1 1 calc R U . . . O6 O 1.1399(4) 1.1222(3) 0.6213(3) 0.0469(9) Uani 1 1 d . . . . . H6C H 1.174(4) 1.190(4) 0.629(3) 0.030(11) Uiso 1 1 d . . . . . H6D H 1.090(5) 1.114(4) 0.641(4) 0.048(16) Uiso 1 1 d . . . . . O7 O 1.1530(3) 0.8984(3) 0.5567(2) 0.0242(5) Uani 1 1 d . . . . . H7A H 1.091(5) 0.873(4) 0.513(4) 0.040(14) Uiso 1 1 d . . . . . H7B H 1.157(5) 0.960(5) 0.568(4) 0.055(17) Uiso 1 1 d . . . . . H8AA H -0.100(5) 0.199(4) 1.018(4) 0.041(16) Uiso 1 1 d . . . . . H8AB H -0.158(6) 0.214(5) 0.955(5) 0.05(2) Uiso 1 1 d . . . . . O10 O 0.0361(12) 0.0404(10) 0.9652(8) 0.271(5) Uani 1 1 d . . . . . H16 H 0.609(3) 0.488(3) 0.885(3) 0.022(10) Uiso 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 O8A 0.026(3) 0.017(3) 0.0280(19) 0.006(2) 0.013(2) 0.009(2) O8B 0.026(3) 0.017(3) 0.0280(19) 0.006(2) 0.013(2) 0.009(2) Cu1 0.00638(16) 0.01121(17) 0.01214(17) 0.00312(13) 0.00267(13) 0.00150(13) Cl1 0.0085(3) 0.0198(4) 0.0149(3) 0.0066(3) 0.0036(3) 0.0015(3) O1 0.0106(10) 0.0129(11) 0.0388(14) 0.0027(10) 0.0059(10) 0.0017(8) O2 0.0090(9) 0.0135(10) 0.0196(11) 0.0067(8) 0.0062(8) 0.0026(8) O3 0.0093(11) 0.0197(12) 0.0148(12) 0.0036(9) 0.0044(10) 0.0028(9) N1 0.0102(11) 0.0093(12) 0.0196(13) 0.0026(10) 0.0062(10) 0.0016(9) N2 0.0111(11) 0.0097(11) 0.0132(12) 0.0018(9) 0.0028(9) 0.0023(9) N3 0.0093(11) 0.0108(11) 0.0103(11) 0.0021(9) 0.0029(9) 0.0024(9) N4 0.0087(11) 0.0118(12) 0.0102(11) 0.0021(9) 0.0025(9) 0.0026(9) N5 0.0101(12) 0.0101(12) 0.0196(13) 0.0043(10) 0.0051(10) 0.0031(10) N6 0.0080(11) 0.0150(13) 0.0116(12) 0.0029(10) 0.0033(10) 0.0018(10) N7 0.0076(11) 0.0108(12) 0.0128(12) 0.0023(9) 0.0035(9) 0.0015(9) N8 0.0083(11) 0.0144(12) 0.0143(12) 0.0024(10) 0.0039(9) 0.0050(10) C1 0.0135(15) 0.0134(15) 0.0338(19) -0.0022(13) 0.0048(13) 0.0028(12) C2 0.0132(14) 0.0116(14) 0.0247(16) 0.0049(12) 0.0059(12) 0.0021(12) C3 0.0121(14) 0.0161(15) 0.0255(17) 0.0055(13) 0.0049(12) 0.0040(12) C4 0.0111(14) 0.0116(14) 0.0256(16) 0.0019(12) 0.0091(12) 0.0023(11) C5 0.0120(13) 0.0140(14) 0.0057(13) 0.0006(11) 0.0017(11) 0.0034(11) C6 0.0095(13) 0.0132(14) 0.0050(12) 0.0004(10) 0.0007(10) 0.0026(11) C7 0.0103(13) 0.0137(14) 0.0058(13) 0.0001(11) 0.0013(10) 0.0032(11) C8 0.0105(13) 0.0130(14) 0.0090(13) 0.0026(11) 0.0014(11) 0.0005(11) C9 0.0131(14) 0.0126(14) 0.0153(14) 0.0050(11) 0.0050(11) 0.0044(11) C10 0.0138(14) 0.0131(14) 0.0105(13) 0.0040(11) 0.0034(11) 0.0051(11) C11 0.0156(15) 0.0163(15) 0.0227(16) 0.0054(12) 0.0072(12) 0.0088(12) Cu2 0.00749(16) 0.01105(17) 0.01516(18) 0.00520(13) 0.00545(13) 0.00491(13) Cl2 0.0120(3) 0.0167(3) 0.0183(3) 0.0064(3) 0.0060(3) 0.0088(3) Cl3 0.0103(3) 0.0180(3) 0.0140(3) 0.0034(3) 0.0050(3) 0.0058(3) O4 0.0235(12) 0.0126(10) 0.0271(12) 0.0054(9) 0.0097(10) 0.0114(9) O5 0.0091(9) 0.0125(10) 0.0194(11) 0.0071(8) 0.0070(8) 0.0066(8) N9 0.0092(11) 0.0077(11) 0.0187(13) 0.0035(9) 0.0039(10) 0.0029(9) N10 0.0094(11) 0.0101(12) 0.0129(12) 0.0011(9) 0.0027(9) 0.0027(9) N11 0.0073(11) 0.0107(11) 0.0119(12) 0.0023(9) 0.0024(9) 0.0033(9) N12 0.0102(11) 0.0085(11) 0.0122(12) 0.0026(9) 0.0037(9) 0.0037(9) N13 0.0083(11) 0.0091(12) 0.0206(13) 0.0053(10) 0.0060(10) 0.0030(10) N14 0.0091(11) 0.0152(13) 0.0153(13) 0.0042(10) 0.0064(11) 0.0066(10) N15 0.0072(11) 0.0120(12) 0.0141(12) 0.0042(9) 0.0052(9) 0.0057(9) N16 0.0062(11) 0.0140(12) 0.0159(12) 0.0040(10) 0.0044(9) 0.0060(10) C12 0.0252(17) 0.0177(16) 0.0281(17) 0.0100(13) 0.0152(14) 0.0129(13) C13 0.0214(16) 0.0128(15) 0.0251(17) 0.0020(13) 0.0013(13) 0.0070(13) C14 0.0099(13) 0.0141(15) 0.0280(17) 0.0065(13) 0.0058(12) 0.0072(11) C15 0.0141(14) 0.0102(14) 0.0266(16) 0.0059(12) 0.0070(12) 0.0039(12) C16 0.0097(13) 0.0108(13) 0.0073(13) -0.0003(10) 0.0002(10) 0.0027(11) C17 0.0091(13) 0.0114(13) 0.0062(12) 0.0001(10) 0.0023(10) 0.0026(11) C18 0.0096(13) 0.0105(13) 0.0068(12) 0.0010(10) 0.0035(10) 0.0030(11) C19 0.0128(13) 0.0098(13) 0.0078(13) 0.0033(10) 0.0043(11) 0.0051(11) C20 0.0105(13) 0.0115(13) 0.0109(13) 0.0034(11) 0.0037(11) 0.0034(11) C21 0.0109(13) 0.0111(14) 0.0087(13) 0.0010(11) 0.0033(11) 0.0018(11) C22 0.0084(13) 0.0174(15) 0.0168(15) 0.0062(12) 0.0033(11) 0.0019(11) O6 0.066(2) 0.0153(15) 0.072(2) 0.0057(14) 0.058(2) 0.0021(14) O7 0.0263(14) 0.0190(14) 0.0252(14) 0.0038(11) 0.0014(11) 0.0096(11) O10 0.331(14) 0.254(12) 0.222(11) 0.087(9) 0.134(10) 0.024(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 H8AA O8A H8AB 60(4) H8AA O8B H8AB 106(7) O2 Cu1 N4 91.94(9) O2 Cu1 N6 166.42(10) N4 Cu1 N6 81.45(10) O2 Cu1 Cl1 90.43(6) N4 Cu1 Cl1 170.32(7) N6 Cu1 Cl1 94.23(7) O2 Cu1 O3 100.56(9) N4 Cu1 O3 87.85(9) N6 Cu1 O3 91.09(9) Cl1 Cu1 O3 100.94(7) C3 O1 C1 110.9(2) C8 O2 Cu1 125.16(18) Cu1 O3 H3A 115(3) Cu1 O3 H3B 136(4) H3A O3 H3B 103(5) C5 N1 C2 122.6(2) C5 N1 C4 123.1(2) C2 N1 C4 113.6(2) C7 N2 C5 114.0(2) C6 N3 C5 114.4(2) C6 N4 C7 114.4(2) C6 N4 Cu1 129.78(19) C7 N4 Cu1 115.40(18) C7 N5 N6 118.1(2) C7 N5 H5 126(2) N6 N5 H5 116(2) N5 N6 Cu1 109.22(17) N5 N6 H6A 105(2) Cu1 N6 H6A 113(2) N5 N6 H6B 109(2) Cu1 N6 H6B 109(2) H6A N6 H6B 111(3) C6 N7 N8 119.1(2) C6 N7 C8 129.9(2) N8 N7 C8 110.9(2) C10 N8 N7 104.2(2) O1 C1 C2 112.1(2) O1 C1 H1A 109.2 C2 C1 H1A 109.2 O1 C1 H1B 109.2 C2 C1 H1B 109.2 H1A C1 H1B 107.9 N1 C2 C1 109.0(2) N1 C2 H2A 109.9 C1 C2 H2A 109.9 N1 C2 H2B 109.9 C1 C2 H2B 109.9 H2A C2 H2B 108.3 O1 C3 C4 110.7(2) O1 C3 H3C 109.5 C4 C3 H3C 109.5 O1 C3 H3D 109.5 C4 C3 H3D 109.5 H3C C3 H3D 108.1 N1 C4 C3 109.4(2) N1 C4 H4A 109.8 C3 C4 H4A 109.8 N1 C4 H4B 109.8 C3 C4 H4B 109.8 H4A C4 H4B 108.2 N1 C5 N2 118.5(2) N1 C5 N3 116.0(2) N2 C5 N3 125.5(3) N3 C6 N4 125.7(3) N3 C6 N7 117.6(2) N4 C6 N7 116.6(2) N2 C7 N5 118.7(3) N2 C7 N4 125.8(2) N5 C7 N4 115.4(2) O2 C8 C9 129.7(3) O2 C8 N7 124.7(2) C9 C8 N7 105.6(2) C8 C9 C10 106.2(2) C8 C9 H9 126.9 C10 C9 H9 126.9 N8 C10 C9 113.1(2) N8 C10 C11 119.9(3) C9 C10 C11 127.0(3) C10 C11 H11A 109.5 C10 C11 H11B 109.5 H11A C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 O5 Cu2 N11 90.89(9) O5 Cu2 N14 166.34(9) N11 Cu2 N14 80.60(10) O5 Cu2 Cl2 92.52(6) N11 Cu2 Cl2 161.34(7) N14 Cu2 Cl2 92.30(7) O5 Cu2 Cl3 99.27(6) N11 Cu2 Cl3 94.16(7) N14 Cu2 Cl3 92.03(8) Cl2 Cu2 Cl3 103.37(3) C12 O4 C13 110.3(2) C19 O5 Cu2 126.25(18) C16 N9 C15 123.1(2) C16 N9 C14 122.5(2) C15 N9 C14 113.9(2) C17 N10 C16 114.6(2) C18 N11 C17 113.0(2) C18 N11 Cu2 130.81(19) C17 N11 Cu2 115.50(17) C18 N12 C16 113.9(2) C17 N13 N14 117.3(2) C17 N13 H13 122(2) N14 N13 H13 119(2) N13 N14 Cu2 110.25(17) N13 N14 H14A 109(2) Cu2 N14 H14A 116(2) N13 N14 H14B 107(3) Cu2 N14 H14B 106(3) H14A N14 H14B 108(3) N16 N15 C18 120.2(2) N16 N15 C19 108.5(2) C18 N15 C19 131.3(2) C21 N16 N15 108.6(2) C21 N16 H16 127(3) N15 N16 H16 124(3) O4 C12 C14 111.2(2) O4 C12 H12A 109.4 C14 C12 H12A 109.4 O4 C12 H12B 109.4 C14 C12 H12B 109.4 H12A C12 H12B 108.0 O4 C13 C15 111.6(2) O4 C13 H13A 109.3 C15 C13 H13A 109.3 O4 C13 H13B 109.3 C15 C13 H13B 109.3 H13A C13 H13B 108.0 N9 C14 C12 109.4(2) N9 C14 H14C 109.8 C12 C14 H14C 109.8 N9 C14 H14D 109.8 C12 C14 H14D 109.8 H14C C14 H14D 108.2 N9 C15 C13 109.3(2) N9 C15 H15A 109.8 C13 C15 H15A 109.8 N9 C15 H15B 109.8 C13 C15 H15B 109.8 H15A C15 H15B 108.3 N9 C16 N10 118.9(2) N9 C16 N12 116.7(2) N10 C16 N12 124.4(2) N10 C17 N13 119.0(2) N10 C17 N11 125.8(2) N13 C17 N11 115.2(2) N12 C18 N11 128.2(3) N12 C18 N15 116.3(2) N11 C18 N15 115.5(2) O5 C19 N15 123.8(2) O5 C19 C20 130.6(3) N15 C19 C20 105.6(2) C21 C20 C19 108.1(2) C21 C20 H20 126.0 C19 C20 H20 126.0 N16 C21 C20 109.2(2) N16 C21 C22 120.4(2) C20 C21 C22 130.3(3) C21 C22 H22A 109.5 C21 C22 H22B 109.5 H22A C22 H22B 109.5 C21 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 H6C O6 H6D 109(5) H7A O7 H7B 101(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O8A H8AA 0.87(5) . O8A H8AB 1.12(5) . O8B H8AA 0.70(5) . O8B H8AB 0.57(5) . Cu1 O2 1.910(2) . Cu1 N4 1.953(2) . Cu1 N6 2.018(2) . Cu1 Cl1 2.2767(7) . Cu1 O3 2.306(2) . O1 C3 1.429(4) . O1 C1 1.430(4) . O2 C8 1.294(3) . O3 H3A 0.69(4) . O3 H3B 0.71(5) . N1 C5 1.341(4) . N1 C2 1.459(4) . N1 C4 1.465(3) . N2 C7 1.324(4) . N2 C5 1.348(4) . N3 C6 1.315(4) . N3 C5 1.361(4) . N4 C6 1.345(3) . N4 C7 1.354(4) . N5 C7 1.341(4) . N5 N6 1.421(3) . N5 H5 0.79(3) . N6 H6A 0.85(4) . N6 H6B 0.92(4) . N7 C6 1.376(4) . N7 N8 1.398(3) . N7 C8 1.408(4) . N8 C10 1.319(4) . C1 C2 1.521(4) . C1 H1A 0.9900 . C1 H1B 0.9900 . C2 H2A 0.9900 . C2 H2B 0.9900 . C3 C4 1.512(4) . C3 H3C 0.9900 . C3 H3D 0.9900 . C4 H4A 0.9900 . C4 H4B 0.9900 . C8 C9 1.374(4) . C9 C10 1.407(4) . C9 H9 0.9500 . C10 C11 1.489(4) . C11 H11A 0.9800 . C11 H11B 0.9800 . C11 H11C 0.9800 . Cu2 O5 1.9418(19) . Cu2 N11 1.962(2) . Cu2 N14 2.013(2) . Cu2 Cl2 2.2778(7) . Cu2 Cl3 2.5706(8) . O4 C12 1.424(4) . O4 C13 1.429(4) . O5 C19 1.272(3) . N9 C16 1.328(4) . N9 C15 1.466(4) . N9 C14 1.468(3) . N10 C17 1.327(4) . N10 C16 1.355(3) . N11 C18 1.337(3) . N11 C17 1.359(4) . N12 C18 1.301(4) . N12 C16 1.369(4) . N13 C17 1.341(3) . N13 N14 1.418(3) . N13 H13 0.83(3) . N14 H14A 0.86(4) . N14 H14B 0.88(4) . N15 N16 1.380(3) . N15 C18 1.393(4) . N15 C19 1.399(3) . N16 C21 1.338(4) . N16 H16 0.82(4) . C12 C14 1.511(4) . C12 H12A 0.9900 . C12 H12B 0.9900 . C13 C15 1.518(4) . C13 H13A 0.9900 . C13 H13B 0.9900 . C14 H14C 0.9900 . C14 H14D 0.9900 . C15 H15A 0.9900 . C15 H15B 0.9900 . C19 C20 1.404(4) . C20 C21 1.378(4) . C20 H20 0.9500 . C21 C22 1.488(4) . C22 H22A 0.9800 . C22 H22B 0.9800 . C22 H22C 0.9800 . O6 H6C 0.78(4) . O6 H6D 0.68(5) . O7 H7A 0.76(5) . O7 H7B 0.72(5) . O10 O10 1.646(16) 2_557 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A N8 0.69(4) 2.15(4) 2.830(3) 173(4) 2_666 O3 H3B Cl2 0.71(5) 2.74(5) 3.395(3) 153(4) 2_566 N5 H5 O7 0.79(3) 2.10(4) 2.842(4) 156(3) 1_455 N6 H6A Cl2 0.85(4) 2.53(4) 3.351(3) 163(3) . N6 H6B Cl1 0.92(4) 2.33(4) 3.220(3) 163(3) 2_566 N13 H13 O8A 0.83(3) 2.07(4) 2.887(14) 168(3) . N13 H13 O8B 0.83(3) 2.12(3) 2.894(6) 155(3) . N14 H14A Cl3 0.86(4) 2.41(4) 3.226(2) 158(3) 2_567 N14 H14B Cl1 0.88(4) 2.58(4) 3.240(3) 132(3) . O6 H6C O2 0.78(4) 2.07(5) 2.835(4) 169(4) 1_665 O6 H6D O1 0.68(5) 2.13(5) 2.777(4) 160(5) . O7 H7A Cl1 0.76(5) 2.95(5) 3.467(3) 127(4) 2_666 O7 H7B O6 0.72(5) 2.08(5) 2.783(4) 166(6) . O8A H8AA Cl2 0.87(5) 2.61(5) 3.471(14) 171(4) 2_567 O8B H8AA Cl2 0.70(5) 2.61(5) 3.232(6) 148(5) 2_567 O8A H8AB Cl3 1.12(5) 2.63(6) 3.718(14) 165(5) 2_567 O8B H8AB Cl3 0.57(5) 2.63(6) 3.179(8) 164(7) 2_567 N16 H16 Cl3 0.82(4) 2.42(4) 3.187(2) 157(3) 2_667