#------------------------------------------------------------------------------ #$Date: 2026-06-22 23:52:58 +0100 (Mon, 22 Jun 2026) $ #$Revision: 306611 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/11/7721148.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_7721148 loop_ _publ_author_name 'Molla, Mofijul' 'Ghosh, Ayyan' 'Ghora, Santanu Ghora' 'Mandal, Sukanta' _publ_section_title ; Copper(II) complexes for electrocatalytic dioxygen reduction: controlling selectivity via proton relay mode ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D6DT00632A _journal_year 2026 _chemical_formula_moiety 'C21 H24 Cu N5 O, F6 P ' _chemical_formula_sum 'C21 H24 Cu F6 N5 O P' _chemical_formula_weight 570.96 _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2025-05-25 deposited with the CCDC. 2026-06-22 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.512(12) _cell_length_b 11.810(5) _cell_length_c 12.716(6) _cell_measurement_reflns_used 6158 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 29.7 _cell_measurement_theta_min 3.1 _cell_volume 2330(2) _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker Saint Plus' _computing_molecular_graphics Mercury _computing_publication_material 'SHELXL-2018 (Sheldrick, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 297(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker SMART 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 0.0765 _diffrn_reflns_av_unetI/netI 0.0657 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 25874 _diffrn_reflns_point_group_measured_fraction_full 0.950 _diffrn_reflns_point_group_measured_fraction_max 0.929 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.722 _diffrn_reflns_theta_min 3.076 _exptl_absorpt_coefficient_mu 1.079 _exptl_absorpt_correction_T_max 0.806 _exptl_absorpt_correction_T_min 0.806 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.628 _exptl_crystal_description block _exptl_crystal_F_000 1164 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.436 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.071 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.32(3) _refine_ls_extinction_coef 0.0066(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 318 _refine_ls_number_reflns 6158 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.1308 _refine_ls_R_factor_gt 0.0589 _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^)+(0.0936P)^2^+0.2996P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1476 _refine_ls_wR_factor_ref 0.1995 _reflns_Friedel_coverage 0.793 _reflns_Friedel_fraction_full 0.897 _reflns_Friedel_fraction_max 0.857 _reflns_number_gt 3182 _reflns_number_total 6158 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt00632a10.cif _cod_data_source_block shelx _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'multi scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_database_code 7721148 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.813 _shelx_estimated_absorpt_t_max 0.813 _shelx_res_file ; TITL SIR2019 run in space group P n a 21 shelx.res created by SHELXL-2018/3 at 10:55:56 on 09-Feb-2025 CELL 0.71073 15.5123 11.8099 12.7159 90.000 90.000 90.000 ZERR 4.00 0.0121 0.0053 0.0063 0.000 0.000 0.000 LATT -1 SYMM - X, - Y, 1/2 + Z SYMM 1/2 - X, 1/2 + Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, Z SFAC C H N O F P CU UNIT 84 96 20 4 24 4 4 MERG 2 FMAP 2 PLAN 1 SIZE 0.200 0.200 0.200 TWIN -1 0 0 0 -1 0 0 0 -1 2 ACTA BOND $H CONF L.S. 20 TEMP 23.90 WGHT 0.093600 0.299600 EXTI 0.006627 BASF 0.32194 FVAR 0.54739 CU 7 0.296913 0.235988 0.100060 11.00000 0.06252 0.05411 = 0.05713 0.00631 0.00093 -0.00200 P1 6 0.535873 -0.107015 0.236167 11.00000 0.07976 0.05571 = 0.07067 -0.00109 0.00228 -0.00195 N1 3 0.364325 0.236696 0.235061 11.00000 0.06415 0.05127 = 0.05960 0.00067 0.00038 0.00291 N5 3 0.283985 0.065570 0.088383 11.00000 0.07491 0.05409 = 0.05303 -0.00280 -0.00101 0.00076 N2 3 0.337575 0.390223 0.095333 11.00000 0.07676 0.05664 = 0.06873 0.01708 0.00008 -0.00035 N4 3 0.163670 0.209974 0.169088 11.00000 0.06799 0.06401 = 0.06124 0.00127 0.00339 0.00468 C14 1 0.108530 0.231609 0.082699 11.00000 0.05009 0.07860 = 0.09703 0.02673 -0.00242 -0.00089 AFIX 23 H14A 2 0.053561 0.259038 0.108648 11.00000 -1.20000 H14B 2 0.098136 0.161391 0.045212 11.00000 -1.20000 AFIX 0 N3 3 0.230349 0.282454 -0.032682 11.00000 0.07146 0.07442 = 0.06798 0.01200 -0.00384 -0.00125 F4 5 0.516576 -0.016813 0.149538 11.00000 0.12245 0.12319 = 0.11920 0.05758 -0.01877 -0.01547 C8 1 0.394968 0.343704 0.258282 11.00000 0.05690 0.05006 = 0.07619 -0.00328 0.00780 0.00013 O1 4 0.332603 0.555565 -0.005783 11.00000 0.11564 0.06312 = 0.11908 0.02999 0.01231 -0.00789 F2 5 0.558523 -0.195001 0.326643 11.00000 0.14680 0.09049 = 0.15845 0.05165 -0.03854 -0.01586 C17 1 0.215547 0.017490 0.136155 11.00000 0.07883 0.05135 = 0.05940 0.00353 -0.00039 -0.00774 C7 1 0.380933 0.428617 0.180720 11.00000 0.06571 0.05226 = 0.08114 0.00173 0.01084 -0.00428 C18 1 0.200750 -0.098886 0.127483 11.00000 0.09499 0.05505 = 0.08521 0.00026 -0.01646 -0.01171 AFIX 43 H18 2 0.152058 -0.130995 0.158001 11.00000 -1.20000 AFIX 0 F1 5 0.522284 -0.205253 0.159445 11.00000 0.27535 0.11035 = 0.13673 -0.05358 0.02012 -0.01238 C9 1 0.437040 0.367279 0.354912 11.00000 0.06071 0.06836 = 0.08026 -0.01431 0.00155 0.00517 F5 5 0.439239 -0.114991 0.263072 11.00000 0.09553 0.15070 = 0.13687 0.04756 0.02040 -0.00395 C4 1 0.468878 0.479086 0.369639 11.00000 0.07260 0.08163 = 0.10051 -0.03513 -0.00030 -0.00453 AFIX 43 H4 2 0.497006 0.498138 0.431755 11.00000 -1.20000 AFIX 0 C3 1 0.445663 0.277368 0.427107 11.00000 0.08139 0.10232 = 0.06457 -0.01073 -0.00508 0.01451 AFIX 43 H3 2 0.473232 0.289626 0.491047 11.00000 -1.20000 AFIX 0 F3 5 0.548049 -0.012737 0.320697 11.00000 0.22866 0.10044 = 0.11048 -0.01916 -0.03771 -0.02397 C2 1 0.414057 0.173000 0.404087 11.00000 0.08406 0.08473 = 0.07430 0.00853 -0.00963 0.00681 AFIX 43 H2 2 0.417664 0.114461 0.452808 11.00000 -1.20000 AFIX 0 C1 1 0.375728 0.155085 0.305081 11.00000 0.08017 0.06148 = 0.06842 0.01199 -0.00821 0.00107 AFIX 43 H1 2 0.357526 0.082333 0.288040 11.00000 -1.20000 AFIX 0 C16 1 0.159722 0.092395 0.201561 11.00000 0.08178 0.07127 = 0.07981 0.01884 0.00985 0.00276 AFIX 23 H16A 2 0.100555 0.066301 0.196873 11.00000 -1.20000 H16B 2 0.177525 0.086695 0.274495 11.00000 -1.20000 AFIX 0 C11 1 0.276537 0.384679 -0.074196 11.00000 0.09921 0.09492 = 0.07302 0.04057 0.00458 -0.00955 AFIX 23 H11A 2 0.320400 0.360292 -0.123621 11.00000 -1.20000 H11B 2 0.235768 0.431658 -0.112167 11.00000 -1.20000 AFIX 0 C12 1 0.222661 0.198269 -0.118245 11.00000 0.08713 0.10642 = 0.07484 0.01208 -0.00875 -0.00020 AFIX 33 H12A 2 0.279124 0.177694 -0.142535 11.00000 -1.50000 H12B 2 0.193546 0.132142 -0.092432 11.00000 -1.50000 H12C 2 0.190321 0.230314 -0.175319 11.00000 -1.50000 AFIX 0 C5 1 0.458245 0.558148 0.293025 11.00000 0.07314 0.06258 = 0.12940 -0.01894 0.01175 -0.00780 AFIX 43 H5 2 0.481211 0.630033 0.303357 11.00000 -1.20000 AFIX 0 C21 1 0.337547 -0.000796 0.034305 11.00000 0.08328 0.08218 = 0.06068 -0.01473 -0.00390 0.01913 AFIX 43 H21 2 0.384281 0.032367 0.000393 11.00000 -1.20000 AFIX 0 C6 1 0.414769 0.536152 0.200518 11.00000 0.07110 0.05472 = 0.11876 -0.00669 0.02000 -0.00289 AFIX 43 H6 2 0.407950 0.593387 0.150979 11.00000 -1.20000 AFIX 0 C20 1 0.326857 -0.115623 0.026432 11.00000 0.10703 0.08777 = 0.08607 -0.03042 -0.01762 0.03373 AFIX 43 H20 2 0.366147 -0.159351 -0.011015 11.00000 -1.20000 AFIX 0 C10 1 0.317890 0.453711 0.009517 11.00000 0.08993 0.06640 = 0.08528 0.02525 0.01449 -0.00121 F6 5 0.632756 -0.096331 0.208235 11.00000 0.10125 0.20489 = 0.25909 0.06291 0.04757 0.01197 C13 1 0.145672 0.317275 0.007795 11.00000 0.07308 0.09938 = 0.08888 0.03091 -0.00933 0.01067 AFIX 23 H13A 2 0.106324 0.327538 -0.050721 11.00000 -1.20000 H13B 2 0.151364 0.389430 0.043572 11.00000 -1.20000 AFIX 0 C15 1 0.145792 0.288484 0.256218 11.00000 0.11536 0.08954 = 0.09580 -0.01693 0.04396 0.01077 AFIX 33 H15A 2 0.183845 0.272305 0.313827 11.00000 -1.50000 H15B 2 0.154742 0.364919 0.232957 11.00000 -1.50000 H15C 2 0.087121 0.279462 0.278728 11.00000 -1.50000 AFIX 0 C19 1 0.257617 -0.164873 0.074421 11.00000 0.14265 0.06125 = 0.10689 -0.02217 -0.04735 0.00943 AFIX 43 H19 2 0.249526 -0.242801 0.070774 11.00000 -1.20000 AFIX 0 HKLF 4 REM SIR2019 run in space group P n a 21 REM wR2 = 0.1995, GooF = S = 1.034, Restrained GooF = 1.034 for all data REM R1 = 0.0589 for 3182 Fo > 4sig(Fo) and 0.1308 for all 6158 data REM 318 parameters refined using 1 restraints END WGHT 0.0922 0.3636 REM Highest difference peak 0.436, deepest hole -0.650, 1-sigma level 0.071 Q1 1 0.5462 0.5952 0.2361 11.00000 0.05 0.44 ; _shelx_res_checksum 43050 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -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 Cu Cu 0.29691(6) 0.23599(7) 0.10006(11) 0.0579(3) Uani 1 1 d . . . . . P1 P 0.53587(16) -0.10701(19) 0.2362(2) 0.0687(6) Uani 1 1 d . . . . . N1 N 0.3643(5) 0.2367(5) 0.2351(6) 0.0583(17) Uani 1 1 d . . . . . N5 N 0.2840(4) 0.0656(5) 0.0884(7) 0.0607(16) Uani 1 1 d . . . . . N2 N 0.3376(5) 0.3902(5) 0.0953(7) 0.0674(17) Uani 1 1 d . . . . . N4 N 0.1637(5) 0.2100(6) 0.1691(6) 0.0644(19) Uani 1 1 d . . . . . C14 C 0.1085(6) 0.2316(7) 0.0827(10) 0.075(3) Uani 1 1 d . . . . . H14A H 0.053561 0.259038 0.108648 0.090 Uiso 1 1 calc R U . . . H14B H 0.098136 0.161391 0.045212 0.090 Uiso 1 1 calc R U . . . N3 N 0.2303(5) 0.2825(6) -0.0327(7) 0.071(2) Uani 1 1 d . . . . . F4 F 0.5166(5) -0.0168(7) 0.1495(6) 0.122(3) Uani 1 1 d . . . . . C8 C 0.3950(5) 0.3437(6) 0.2583(8) 0.061(2) Uani 1 1 d . . . . . O1 O 0.3326(5) 0.5556(6) -0.0058(7) 0.099(2) Uani 1 1 d . . . . . F2 F 0.5585(6) -0.1950(7) 0.3266(8) 0.132(3) Uani 1 1 d . . . . . C17 C 0.2155(6) 0.0175(7) 0.1362(7) 0.063(2) Uani 1 1 d . . . . . C7 C 0.3809(6) 0.4286(7) 0.1807(8) 0.066(2) Uani 1 1 d . . . . . C18 C 0.2007(7) -0.0989(7) 0.1275(8) 0.078(3) Uani 1 1 d . . . . . H18 H 0.152058 -0.130995 0.158001 0.094 Uiso 1 1 calc R U . . . F1 F 0.5223(9) -0.2053(8) 0.1594(9) 0.174(4) Uani 1 1 d . . . . . C9 C 0.4370(6) 0.3673(8) 0.3549(9) 0.070(2) Uani 1 1 d . . . . . F5 F 0.4392(4) -0.1150(7) 0.2631(7) 0.128(3) Uani 1 1 d . . . . . C4 C 0.4689(7) 0.4791(10) 0.3696(10) 0.085(3) Uani 1 1 d . . . . . H4 H 0.497006 0.498138 0.431755 0.102 Uiso 1 1 calc R U . . . C3 C 0.4457(7) 0.2774(10) 0.4271(10) 0.083(3) Uani 1 1 d . . . . . H3 H 0.473232 0.289626 0.491047 0.099 Uiso 1 1 calc R U . . . F3 F 0.5480(7) -0.0127(7) 0.3207(7) 0.147(4) Uani 1 1 d . . . . . C2 C 0.4141(7) 0.1730(10) 0.4041(9) 0.081(3) Uani 1 1 d . . . . . H2 H 0.417664 0.114461 0.452808 0.097 Uiso 1 1 calc R U . . . C1 C 0.3757(6) 0.1551(8) 0.3051(8) 0.070(2) Uani 1 1 d . . . . . H1 H 0.357526 0.082333 0.288040 0.084 Uiso 1 1 calc R U . . . C16 C 0.1597(6) 0.0924(8) 0.2016(9) 0.078(3) Uani 1 1 d . . . . . H16A H 0.100555 0.066301 0.196873 0.093 Uiso 1 1 calc R U . . . H16B H 0.177525 0.086695 0.274495 0.093 Uiso 1 1 calc R U . . . C11 C 0.2765(8) 0.3847(10) -0.0742(9) 0.089(3) Uani 1 1 d . . . . . H11A H 0.320400 0.360292 -0.123621 0.107 Uiso 1 1 calc R U . . . H11B H 0.235768 0.431658 -0.112167 0.107 Uiso 1 1 calc R U . . . C12 C 0.2227(8) 0.1983(11) -0.1182(10) 0.089(3) Uani 1 1 d . . . . . H12A H 0.279124 0.177694 -0.142535 0.134 Uiso 1 1 calc R U . . . H12B H 0.193546 0.132142 -0.092432 0.134 Uiso 1 1 calc R U . . . H12C H 0.190321 0.230314 -0.175319 0.134 Uiso 1 1 calc R U . . . C5 C 0.4582(6) 0.5581(9) 0.2930(12) 0.088(4) Uani 1 1 d . . . . . H5 H 0.481211 0.630033 0.303357 0.106 Uiso 1 1 calc R U . . . C21 C 0.3375(7) -0.0008(8) 0.0343(8) 0.075(3) Uani 1 1 d . . . . . H21 H 0.384281 0.032367 0.000393 0.090 Uiso 1 1 calc R U . . . C6 C 0.4148(7) 0.5362(8) 0.2005(10) 0.082(3) Uani 1 1 d . . . . . H6 H 0.407950 0.593387 0.150979 0.098 Uiso 1 1 calc R U . . . C20 C 0.3269(9) -0.1156(10) 0.0264(10) 0.094(4) Uani 1 1 d . . . . . H20 H 0.366147 -0.159351 -0.011015 0.112 Uiso 1 1 calc R U . . . C10 C 0.3179(7) 0.4537(8) 0.0095(9) 0.081(3) Uani 1 1 d . . . . . F6 F 0.6328(6) -0.0963(10) 0.2082(11) 0.188(5) Uani 1 1 d . . . . . C13 C 0.1457(6) 0.3173(10) 0.0078(10) 0.087(3) Uani 1 1 d . . . . . H13A H 0.106324 0.327538 -0.050721 0.105 Uiso 1 1 calc R U . . . H13B H 0.151364 0.389430 0.043572 0.105 Uiso 1 1 calc R U . . . C15 C 0.1458(9) 0.2885(10) 0.2562(11) 0.100(4) Uani 1 1 d . . . . . H15A H 0.183845 0.272305 0.313827 0.150 Uiso 1 1 calc R U . . . H15B H 0.154742 0.364919 0.232957 0.150 Uiso 1 1 calc R U . . . H15C H 0.087121 0.279462 0.278728 0.150 Uiso 1 1 calc R U . . . C19 C 0.2576(10) -0.1649(9) 0.0744(11) 0.104(4) Uani 1 1 d . . . . . H19 H 0.249526 -0.242801 0.070774 0.124 Uiso 1 1 calc R 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 Cu 0.0625(5) 0.0541(5) 0.0571(6) 0.0063(7) 0.0009(6) -0.0020(4) P1 0.0798(16) 0.0557(12) 0.0707(15) -0.0011(11) 0.0023(12) -0.0020(11) N1 0.064(4) 0.051(3) 0.060(4) 0.001(3) 0.000(3) 0.003(3) N5 0.075(4) 0.054(3) 0.053(4) -0.003(4) -0.001(4) 0.001(3) N2 0.077(4) 0.057(3) 0.069(4) 0.017(5) 0.000(5) 0.000(3) N4 0.068(5) 0.064(4) 0.061(5) 0.001(4) 0.003(4) 0.005(4) C14 0.050(4) 0.079(5) 0.097(10) 0.027(6) -0.002(5) -0.001(4) N3 0.071(5) 0.074(5) 0.068(5) 0.012(4) -0.004(4) -0.001(4) F4 0.122(5) 0.123(5) 0.119(5) 0.058(5) -0.019(5) -0.015(5) C8 0.057(5) 0.050(4) 0.076(6) -0.003(4) 0.008(4) 0.000(4) O1 0.116(6) 0.063(4) 0.119(6) 0.030(4) 0.012(5) -0.008(4) F2 0.147(7) 0.090(5) 0.158(9) 0.052(6) -0.039(6) -0.016(5) C17 0.079(6) 0.051(4) 0.059(5) 0.004(3) 0.000(4) -0.008(4) C7 0.066(5) 0.052(4) 0.081(6) 0.002(4) 0.011(5) -0.004(4) C18 0.095(7) 0.055(5) 0.085(8) 0.000(4) -0.016(5) -0.012(5) F1 0.275(13) 0.110(6) 0.137(9) -0.054(6) 0.020(8) -0.012(8) C9 0.061(5) 0.068(5) 0.080(7) -0.014(5) 0.002(5) 0.005(4) F5 0.096(5) 0.151(7) 0.137(7) 0.048(6) 0.020(4) -0.004(4) C4 0.073(7) 0.082(7) 0.101(9) -0.035(6) 0.000(5) -0.005(5) C3 0.081(7) 0.102(8) 0.065(7) -0.011(6) -0.005(5) 0.015(6) F3 0.229(11) 0.100(5) 0.110(7) -0.019(5) -0.038(6) -0.024(6) C2 0.084(7) 0.085(7) 0.074(7) 0.009(6) -0.010(6) 0.007(6) C1 0.080(6) 0.061(5) 0.068(6) 0.012(5) -0.008(5) 0.001(5) C16 0.082(7) 0.071(6) 0.080(7) 0.019(5) 0.010(5) 0.003(5) C11 0.099(8) 0.095(7) 0.073(7) 0.041(6) 0.005(6) -0.010(6) C12 0.087(7) 0.106(8) 0.075(7) 0.012(6) -0.009(6) 0.000(7) C5 0.073(7) 0.063(6) 0.129(11) -0.019(7) 0.012(6) -0.008(5) C21 0.083(7) 0.082(7) 0.061(6) -0.015(5) -0.004(5) 0.019(5) C6 0.071(6) 0.055(5) 0.119(9) -0.007(5) 0.020(6) -0.003(5) C20 0.107(9) 0.088(8) 0.086(8) -0.030(6) -0.018(7) 0.034(7) C10 0.090(7) 0.066(6) 0.085(7) 0.025(5) 0.014(6) -0.001(5) F6 0.101(6) 0.205(10) 0.259(14) 0.063(10) 0.048(8) 0.012(7) C13 0.073(7) 0.099(8) 0.089(8) 0.031(6) -0.009(6) 0.011(6) C15 0.115(10) 0.090(7) 0.096(9) -0.017(7) 0.044(8) 0.011(7) C19 0.143(11) 0.061(6) 0.107(11) -0.022(6) -0.047(9) 0.009(7) 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' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' 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 N2 Cu N1 81.5(3) . . ? N2 Cu N5 165.3(3) . . ? N1 Cu N5 96.8(3) . . ? N2 Cu N3 83.5(3) . . ? N1 Cu N3 164.3(3) . . ? N5 Cu N3 98.9(3) . . ? N2 Cu N4 116.0(3) . . ? N1 Cu N4 98.3(3) . . ? N5 Cu N4 78.7(3) . . ? N3 Cu N4 84.0(3) . . ? F1 P1 F5 87.8(6) . . ? F1 P1 F6 92.8(7) . . ? F5 P1 F6 178.8(6) . . ? F1 P1 F3 176.0(6) . . ? F5 P1 F3 90.5(6) . . ? F6 P1 F3 89.0(7) . . ? F1 P1 F4 92.4(6) . . ? F5 P1 F4 90.7(4) . . ? F6 P1 F4 88.2(5) . . ? F3 P1 F4 91.3(4) . . ? F1 P1 F2 89.8(6) . . ? F5 P1 F2 90.8(5) . . ? F6 P1 F2 90.3(6) . . ? F3 P1 F2 86.6(5) . . ? F4 P1 F2 177.4(5) . . ? C1 N1 C8 118.4(8) . . ? C1 N1 Cu 129.9(6) . . ? C8 N1 Cu 111.4(6) . . ? C21 N5 C17 118.4(8) . . ? C21 N5 Cu 124.0(7) . . ? C17 N5 Cu 117.6(6) . . ? C7 N2 C10 124.8(8) . . ? C7 N2 Cu 117.0(6) . . ? C10 N2 Cu 118.2(7) . . ? C14 N4 C16 111.6(8) . . ? C14 N4 C15 110.9(9) . . ? C16 N4 C15 112.4(9) . . ? C14 N4 Cu 103.1(6) . . ? C16 N4 Cu 106.2(5) . . ? C15 N4 Cu 112.2(7) . . ? N4 C14 C13 112.4(7) . . ? N4 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? N4 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C13 N3 C12 111.9(9) . . ? C13 N3 C11 109.0(8) . . ? C12 N3 C11 108.7(9) . . ? C13 N3 Cu 103.7(6) . . ? C12 N3 Cu 117.8(7) . . ? C11 N3 Cu 105.3(6) . . ? N1 C8 C9 121.5(8) . . ? N1 C8 C7 116.3(8) . . ? C9 C8 C7 122.2(8) . . ? N5 C17 C18 120.5(9) . . ? N5 C17 C16 117.3(7) . . ? C18 C17 C16 122.1(8) . . ? N2 C7 C6 129.4(9) . . ? N2 C7 C8 113.3(7) . . ? C6 C7 C8 117.3(10) . . ? C19 C18 C17 119.8(10) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C3 C9 C8 117.4(9) . . ? C3 C9 C4 125.5(11) . . ? C8 C9 C4 117.1(10) . . ? C5 C4 C9 120.1(11) . . ? C5 C4 H4 120.0 . . ? C9 C4 H4 120.0 . . ? C2 C3 C9 120.6(11) . . ? C2 C3 H3 119.7 . . ? C9 C3 H3 119.7 . . ? C3 C2 C1 118.8(10) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? N1 C1 C2 123.2(9) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? N4 C16 C17 112.6(8) . . ? N4 C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? N4 C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C10 C11 N3 113.3(8) . . ? C10 C11 H11A 108.9 . . ? N3 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? N3 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C4 C5 C6 122.7(10) . . ? C4 C5 H5 118.6 . . ? C6 C5 H5 118.6 . . ? N5 C21 C20 123.0(11) . . ? N5 C21 H21 118.5 . . ? C20 C21 H21 118.5 . . ? C5 C6 C7 120.5(11) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C19 C20 C21 119.0(11) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? O1 C10 N2 128.3(12) . . ? O1 C10 C11 120.0(10) . . ? N2 C10 C11 111.7(8) . . ? N3 C13 C14 112.1(8) . . ? N3 C13 H13A 109.2 . . ? C14 C13 H13A 109.2 . . ? N3 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? N4 C15 H15A 109.5 . . ? N4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C18 C19 C20 119.3(10) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? 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 Cu N2 1.929(6) . ? Cu N1 2.010(8) . ? Cu N5 2.028(6) . ? Cu N3 2.053(8) . ? Cu N4 2.266(8) . ? P1 F1 1.530(9) . ? P1 F5 1.540(7) . ? P1 F6 1.549(8) . ? P1 F3 1.559(8) . ? P1 F4 1.561(7) . ? P1 F2 1.590(8) . ? N1 C1 1.324(11) . ? N1 C8 1.382(10) . ? N5 C21 1.333(11) . ? N5 C17 1.349(11) . ? N2 C7 1.355(13) . ? N2 C10 1.359(13) . ? N4 C14 1.415(14) . ? N4 C16 1.450(11) . ? N4 C15 1.471(14) . ? C14 C13 1.504(14) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? N3 C13 1.469(13) . ? N3 C12 1.479(15) . ? N3 C11 1.500(11) . ? C8 C9 1.419(14) . ? C8 C7 1.423(13) . ? O1 C10 1.240(11) . ? C17 C18 1.398(11) . ? C17 C16 1.491(13) . ? C7 C6 1.397(13) . ? C18 C19 1.357(16) . ? C18 H18 0.9300 . ? C9 C3 1.410(15) . ? C9 C4 1.422(14) . ? C4 C5 1.359(18) . ? C4 H4 0.9300 . ? C3 C2 1.358(16) . ? C3 H3 0.9300 . ? C2 C1 1.408(14) . ? C2 H2 0.9300 . ? C1 H1 0.9300 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C11 C10 1.486(16) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C5 C6 1.381(17) . ? C5 H5 0.9300 . ? C21 C20 1.370(14) . ? C21 H21 0.9300 . ? C6 H6 0.9300 . ? C20 C19 1.365(18) . ? C20 H20 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C19 H19 0.9300 . ? 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 C16 N4 C14 C13 -144.6(9) . . . . ? C15 N4 C14 C13 89.3(12) . . . . ? Cu N4 C14 C13 -31.0(10) . . . . ? C1 N1 C8 C9 -0.6(13) . . . . ? Cu N1 C8 C9 173.7(7) . . . . ? C1 N1 C8 C7 -179.8(8) . . . . ? Cu N1 C8 C7 -5.6(9) . . . . ? C21 N5 C17 C18 -1.0(13) . . . . ? Cu N5 C17 C18 177.3(7) . . . . ? C21 N5 C17 C16 176.3(9) . . . . ? Cu N5 C17 C16 -5.4(11) . . . . ? C10 N2 C7 C6 -0.5(16) . . . . ? Cu N2 C7 C6 -177.6(8) . . . . ? C10 N2 C7 C8 -178.4(8) . . . . ? Cu N2 C7 C8 4.5(10) . . . . ? N1 C8 C7 N2 1.0(11) . . . . ? C9 C8 C7 N2 -178.2(8) . . . . ? N1 C8 C7 C6 -177.2(8) . . . . ? C9 C8 C7 C6 3.6(13) . . . . ? N5 C17 C18 C19 2.9(14) . . . . ? C16 C17 C18 C19 -174.3(10) . . . . ? N1 C8 C9 C3 -0.6(13) . . . . ? C7 C8 C9 C3 178.5(9) . . . . ? N1 C8 C9 C4 177.8(8) . . . . ? C7 C8 C9 C4 -3.0(13) . . . . ? C3 C9 C4 C5 178.5(11) . . . . ? C8 C9 C4 C5 0.2(14) . . . . ? C8 C9 C3 C2 -0.4(15) . . . . ? C4 C9 C3 C2 -178.8(10) . . . . ? C9 C3 C2 C1 2.6(16) . . . . ? C8 N1 C1 C2 3.0(14) . . . . ? Cu N1 C1 C2 -170.1(8) . . . . ? C3 C2 C1 N1 -4.0(16) . . . . ? C14 N4 C16 C17 82.2(10) . . . . ? C15 N4 C16 C17 -152.5(9) . . . . ? Cu N4 C16 C17 -29.4(9) . . . . ? N5 C17 C16 N4 25.4(12) . . . . ? C18 C17 C16 N4 -157.4(9) . . . . ? C13 N3 C11 C10 80.2(12) . . . . ? C12 N3 C11 C10 -157.5(10) . . . . ? Cu N3 C11 C10 -30.4(11) . . . . ? C9 C4 C5 C6 2.1(17) . . . . ? C17 N5 C21 C20 -1.0(15) . . . . ? Cu N5 C21 C20 -179.1(8) . . . . ? C4 C5 C6 C7 -1.4(16) . . . . ? N2 C7 C6 C5 -179.2(10) . . . . ? C8 C7 C6 C5 -1.4(14) . . . . ? N5 C21 C20 C19 1.1(18) . . . . ? C7 N2 C10 O1 -2.3(18) . . . . ? Cu N2 C10 O1 174.7(9) . . . . ? C7 N2 C10 C11 175.3(9) . . . . ? Cu N2 C10 C11 -7.7(12) . . . . ? N3 C11 C10 O1 -156.0(10) . . . . ? N3 C11 C10 N2 26.2(13) . . . . ? C12 N3 C13 C14 79.4(12) . . . . ? C11 N3 C13 C14 -160.3(10) . . . . ? Cu N3 C13 C14 -48.5(11) . . . . ? N4 C14 C13 N3 57.3(14) . . . . ? C17 C18 C19 C20 -2.7(16) . . . . ? C21 C20 C19 C18 0.8(18) . . . . ?