#------------------------------------------------------------------------------ #$Date: 2021-03-27 07:24:52 +0200 (Sat, 27 Mar 2021) $ #$Revision: 263388 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/25/7242551.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_7242551 loop_ _publ_author_name 'Klongdee, Fatima' 'Leelasubcharoen, Somying' 'Youngme, Sujittra' 'Boonmak, Jaursup' _publ_section_title ; Sonochemical synthesis of a trinuclear Cu(ii) complex with open coordination sites for the differentiable optical detection of volatile amines ; _journal_issue 20 _journal_name_full 'RSC Advances' _journal_page_first 12218 _journal_page_last 12226 _journal_paper_doi 10.1039/D1RA01151K _journal_volume 11 _journal_year 2021 _chemical_formula_moiety 'C30 H28 Cu3 N10 O12' _chemical_formula_sum 'C30 H28 Cu3 N10 O12' _chemical_formula_weight 911.24 _chemical_name_common {tetraaqua-bis(2,2'-dipyridylamine)-bis(mu-pyrazole-3,5-dicarbarboxylato)tricopper(II)} _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 mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-02-09 deposited with the CCDC. 2021-03-11 downloaded from the CCDC. ; _cell_angle_alpha 106.045(6) _cell_angle_beta 104.318(7) _cell_angle_gamma 99.588(6) _cell_formula_units_Z 1 _cell_length_a 7.5789(18) _cell_length_b 9.937(2) _cell_length_c 11.529(3) _cell_measurement_reflns_used 1789 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 23.228 _cell_measurement_theta_min 3.381 _cell_volume 782.4(3) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_collection BrukerAPEX2 _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics SHELXL _computing_publication_material SHELXL _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type ; Bruker D8 QUEST PHOTON 100 ; _diffrn_measurement_method '\fand\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1232 _diffrn_reflns_av_unetI/netI 0.1164 _diffrn_reflns_Laue_measured_fraction_full 0.901 _diffrn_reflns_Laue_measured_fraction_max 0.901 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 9594 _diffrn_reflns_point_group_measured_fraction_full 0.901 _diffrn_reflns_point_group_measured_fraction_max 0.901 _diffrn_reflns_theta_full 24.511 _diffrn_reflns_theta_max 24.511 _diffrn_reflns_theta_min 3.145 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 2.107 _exptl_absorpt_correction_T_max 0.7451 _exptl_absorpt_correction_T_min 0.6142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS-2012/1 _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.934 _exptl_crystal_description block _exptl_crystal_F_000 461 _exptl_crystal_size_max 0.070 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.030 _refine_diff_density_max 1.072 _refine_diff_density_min -1.168 _refine_diff_density_rms 0.198 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 266 _refine_ls_number_reflns 2359 _refine_ls_number_restraints 214 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.1535 _refine_ls_R_factor_gt 0.0894 _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^)+(0.1442P)^2^+4.1594P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2246 _refine_ls_wR_factor_ref 0.2598 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1465 _reflns_number_total 2359 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ra01151k2.cif _cod_data_source_block Cupzdcdpyam1_a _cod_database_code 7242551 _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_min 0.866 _shelx_estimated_absorpt_t_max 0.939 _shelx_res_file ; Cupzdcdpyam1_a.res created by SHELXL-2014/7 TITL Cupzdcdpyam1_a.res in P-1 CELL 0.71073 7.5789 9.9368 11.5294 106.045 104.318 99.588 ZERR 1.000 0.0018 0.0024 0.0028 0.006 0.007 0.006 LATT 1 SFAC C H N O Cu UNIT 30 28 10 12 3 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! L.S. 100 ACTA BOND $H FMAP 2 PLAN 5 SIZE 0.03 0.05 0.07 DFIX 0.9 0.001 O6 H11 O6 H13 DFIX 1.5 0.001 H11 H13 DANG 1.34 H1 H6 DFIX 0.85 O5 H1 O5 H6 SADI Cu2 H1 Cu2 H6 DELU 0.01 O1 > C15 SIMU 0.01 O1 > C15 TEMP 298 WGHT 0.144200 4.159400 FVAR 0.54614 CU1 5 0.500000 0.500000 0.500000 10.50000 0.03733 0.03361 = 0.04385 0.02556 0.02503 0.02708 CU2 5 0.517582 0.237487 0.752205 11.00000 0.04173 0.03650 = 0.04085 0.01885 0.02090 0.01685 O1 4 0.640300 0.060321 0.720739 11.00000 0.03836 0.02280 = 0.03832 0.01718 0.01492 0.00791 O2 4 0.808942 -0.043218 0.604598 11.00000 0.04754 0.02099 = 0.04233 0.01357 0.01454 0.01968 O3 4 0.656846 0.492541 0.384348 11.00000 0.03559 0.02323 = 0.03238 0.01934 0.01542 0.01911 O4 4 0.862975 0.378492 0.319584 11.00000 0.03301 0.03485 = 0.02924 0.01773 0.01820 0.01963 O5 4 0.252270 0.231112 0.639367 11.00000 0.03089 0.03372 = 0.03568 0.01607 0.01641 0.01274 O6 4 0.225514 0.301130 0.340464 11.00000 0.04063 0.02950 = 0.04620 0.02042 0.01487 0.01284 H6 2 0.282406 0.300657 0.613878 11.00000 0.05113 N1 3 0.409505 0.172088 0.876672 11.00000 0.02454 0.01934 = 0.03247 0.01223 0.00548 0.01171 N2 3 0.659992 0.427017 0.896323 11.00000 0.02664 0.02012 = 0.03241 0.00906 0.00551 0.00990 N3 3 0.651160 0.324359 1.058068 11.00000 0.02427 0.02951 = 0.03034 0.01412 0.00108 0.00794 AFIX 43 H3 2 0.718103 0.324903 1.130361 11.00000 -1.20000 AFIX 0 N4 3 0.619621 0.260509 0.612868 11.00000 0.02072 0.01503 = 0.03121 0.01435 0.00921 0.00989 N5 3 0.628236 0.352773 0.545895 11.00000 0.02251 0.01914 = 0.03306 0.01140 0.01517 0.01193 C1 1 0.496115 0.214141 1.001469 11.00000 0.01982 0.02190 = 0.03503 0.01278 0.00615 0.01186 C2 1 0.429613 0.140876 1.075549 11.00000 0.03045 0.02294 = 0.03480 0.01105 0.01211 0.01149 AFIX 43 H2 2 0.493961 0.167511 1.161609 11.00000 -1.20000 AFIX 0 C3 1 0.272386 0.031663 1.022566 11.00000 0.03165 0.02025 = 0.03869 0.01225 0.01588 0.00872 AFIX 43 H3A 2 0.227265 -0.017195 1.071633 11.00000 -1.20000 AFIX 0 C4 1 0.177884 -0.007377 0.893113 11.00000 0.02674 0.02460 = 0.04043 0.00981 0.01300 0.00462 AFIX 43 H4 2 0.068141 -0.081621 0.854811 11.00000 -1.20000 AFIX 0 C5 1 0.248963 0.064756 0.824731 11.00000 0.03025 0.02023 = 0.03438 0.00913 0.01104 0.00703 AFIX 43 H5 2 0.185298 0.039807 0.738739 11.00000 -1.20000 AFIX 0 C6 1 0.723874 0.439680 1.019887 11.00000 0.02109 0.01973 = 0.03130 0.01088 0.01086 0.01056 C7 1 0.857571 0.557491 1.108104 11.00000 0.02357 0.02523 = 0.03124 0.00495 0.00930 0.00778 AFIX 43 H7 2 0.897274 0.563015 1.192715 11.00000 -1.20000 AFIX 0 C8 1 0.931130 0.665375 1.071260 11.00000 0.02131 0.02703 = 0.03408 0.00329 0.00947 0.00382 AFIX 43 H8 2 1.026479 0.743948 1.129496 11.00000 -1.20000 AFIX 0 C9 1 0.864578 0.658801 0.947105 11.00000 0.02727 0.02257 = 0.03971 0.01428 0.01260 0.00621 AFIX 43 H9 2 0.910534 0.734883 0.921620 11.00000 -1.20000 AFIX 0 C10 1 0.731455 0.540641 0.862003 11.00000 0.03304 0.02459 = 0.03163 0.01138 0.00795 0.01287 AFIX 43 H10 2 0.687494 0.536674 0.778029 11.00000 -1.20000 AFIX 0 C11 1 0.726834 0.168224 0.579640 11.00000 0.02378 0.01227 = 0.02878 0.01001 0.00508 0.00510 C12 1 0.801695 0.199355 0.492496 11.00000 0.02519 0.01362 = 0.02911 0.00285 0.01182 0.00673 AFIX 43 H12 2 0.879413 0.152644 0.454091 11.00000 -1.20000 AFIX 0 C13 1 0.736981 0.316601 0.472860 11.00000 0.02422 0.01918 = 0.02688 0.00971 0.01167 0.00994 C14 1 0.727664 0.052347 0.639264 11.00000 0.02932 0.01251 = 0.03139 0.00864 0.00467 0.00691 C15 1 0.759973 0.400426 0.386238 11.00000 0.02983 0.02611 = 0.02754 0.01063 0.01354 0.01694 H1 2 0.239347 0.157528 0.576214 11.00000 0.05318 H11 2 0.134057 0.348571 0.335744 11.00000 0.03934 H13 2 0.182749 0.207108 0.330007 11.00000 0.25421 HKLF 4 REM Cupzdcdpyam1_a.res in P-1 REM R1 = 0.0894 for 1465 Fo > 4sig(Fo) and 0.1535 for all 2359 data REM 266 parameters refined using 214 restraints END WGHT 0.1442 4.1594 REM Highest difference peak 1.072, deepest hole -1.168, 1-sigma level 0.198 Q1 1 0.3456 0.4461 0.4376 11.00000 0.05 1.07 Q2 1 0.4072 0.1960 0.8054 11.00000 0.05 1.03 Q3 1 0.5100 0.2247 0.6337 11.00000 0.05 0.98 Q4 1 0.4553 0.2173 0.8442 11.00000 0.05 0.97 Q5 1 0.3901 0.4598 0.5350 11.00000 0.05 0.90 ; _shelx_res_checksum 47180 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 0.5000 0.5000 0.5000 0.0308(7) Uani 1 2 d S . P . . Cu2 Cu 0.5176(3) 0.23749(18) 0.75221(16) 0.0359(6) Uani 1 1 d D . . . . O1 O 0.6403(13) 0.0603(9) 0.7207(8) 0.031(2) Uani 1 1 d . U . . . O2 O 0.8089(13) -0.0432(9) 0.6046(8) 0.035(2) Uani 1 1 d . U . . . O3 O 0.6568(12) 0.4925(8) 0.3843(8) 0.0258(19) Uani 1 1 d . U . . . O4 O 0.8630(12) 0.3785(9) 0.3196(8) 0.028(2) Uani 1 1 d . U . . . O5 O 0.2523(13) 0.2311(10) 0.6394(9) 0.031(2) Uani 1 1 d D . . . . O6 O 0.2255(13) 0.3011(9) 0.3405(9) 0.036(2) Uani 1 1 d D . . . . H6 H 0.282(14) 0.301(7) 0.614(9) 0.05(5) Uiso 1 1 d D . . . . N1 N 0.4095(15) 0.1721(10) 0.8767(10) 0.025(2) Uani 1 1 d . U . . . N2 N 0.6600(15) 0.4270(10) 0.8963(10) 0.027(2) Uani 1 1 d . U . . . N3 N 0.6512(15) 0.3244(11) 1.0581(10) 0.028(2) Uani 1 1 d . U . . . H3 H 0.7181 0.3249 1.1304 0.034 Uiso 1 1 calc R U . . . N4 N 0.6196(14) 0.2605(9) 0.6129(9) 0.0200(19) Uani 1 1 d . U . . . N5 N 0.6282(14) 0.3528(10) 0.5459(9) 0.022(2) Uani 1 1 d . U . . . C1 C 0.4961(18) 0.2141(13) 1.0015(12) 0.024(2) Uani 1 1 d . U . . . C2 C 0.4296(19) 0.1409(13) 1.0755(13) 0.028(2) Uani 1 1 d . U . . . H2 H 0.4940 0.1675 1.1616 0.034 Uiso 1 1 calc R U . . . C3 C 0.2724(19) 0.0317(13) 1.0226(12) 0.028(2) Uani 1 1 d . U . . . H3A H 0.2273 -0.0172 1.0716 0.034 Uiso 1 1 calc R U . . . C4 C 0.1779(19) -0.0074(14) 0.8931(13) 0.031(2) Uani 1 1 d . U . . . H4 H 0.0681 -0.0816 0.8548 0.037 Uiso 1 1 calc R U . . . C5 C 0.2490(19) 0.0648(12) 0.8247(13) 0.028(2) Uani 1 1 d . U . . . H5 H 0.1853 0.0398 0.7387 0.034 Uiso 1 1 calc R U . . . C6 C 0.7239(17) 0.4397(12) 1.0199(12) 0.022(2) Uani 1 1 d . U . . . C7 C 0.8576(18) 0.5575(13) 1.1081(12) 0.027(2) Uani 1 1 d . U . . . H7 H 0.8973 0.5630 1.1927 0.033 Uiso 1 1 calc R U . . . C8 C 0.9311(19) 0.6654(14) 1.0713(12) 0.029(2) Uani 1 1 d . U . . . H8 H 1.0265 0.7439 1.1295 0.035 Uiso 1 1 calc R U . . . C9 C 0.8646(18) 0.6588(13) 0.9471(12) 0.029(2) Uani 1 1 d . U . . . H9 H 0.9105 0.7349 0.9216 0.034 Uiso 1 1 calc R U . . . C10 C 0.7315(18) 0.5406(13) 0.8620(13) 0.029(2) Uani 1 1 d . U . . . H10 H 0.6875 0.5367 0.7780 0.035 Uiso 1 1 calc R U . . . C11 C 0.7268(17) 0.1682(12) 0.5796(11) 0.021(2) Uani 1 1 d . U . . . C12 C 0.8017(17) 0.1994(12) 0.4925(11) 0.023(2) Uani 1 1 d . U . . . H12 H 0.8794 0.1526 0.4541 0.027 Uiso 1 1 calc R U . . . C13 C 0.7370(17) 0.3166(12) 0.4729(11) 0.022(2) Uani 1 1 d . U . . . C14 C 0.7277(18) 0.0523(12) 0.6393(12) 0.025(2) Uani 1 1 d . U . . . C15 C 0.7600(18) 0.4004(13) 0.3862(11) 0.025(2) Uani 1 1 d . U . . . H1 H 0.239(16) 0.158(7) 0.576(6) 0.05(5) Uiso 1 1 d D . . . . H11 H 0.134(3) 0.349(3) 0.336(9) 0.04(4) Uiso 1 1 d D . . . . H13 H 0.183(6) 0.207(2) 0.330(8) 0.25(17) Uiso 1 1 d 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 0.0373(16) 0.0336(13) 0.0439(15) 0.0256(12) 0.0250(13) 0.0271(12) Cu2 0.0417(13) 0.0365(10) 0.0408(11) 0.0188(9) 0.0209(10) 0.0168(9) O1 0.038(5) 0.023(4) 0.038(5) 0.017(4) 0.015(4) 0.008(4) O2 0.048(6) 0.021(4) 0.042(5) 0.014(4) 0.015(5) 0.020(4) O3 0.036(5) 0.023(4) 0.032(5) 0.019(4) 0.015(4) 0.019(4) O4 0.033(5) 0.035(5) 0.029(5) 0.018(4) 0.018(4) 0.020(4) O5 0.031(6) 0.034(5) 0.036(6) 0.016(5) 0.016(5) 0.013(5) O6 0.041(6) 0.029(5) 0.046(6) 0.020(5) 0.015(5) 0.013(5) N1 0.025(5) 0.019(4) 0.032(4) 0.012(4) 0.005(4) 0.012(4) N2 0.027(5) 0.020(4) 0.032(4) 0.009(4) 0.006(4) 0.010(4) N3 0.024(5) 0.030(4) 0.030(5) 0.014(4) 0.001(4) 0.008(4) N4 0.021(5) 0.015(4) 0.031(5) 0.014(4) 0.009(4) 0.010(4) N5 0.023(5) 0.019(4) 0.033(5) 0.011(4) 0.015(4) 0.012(4) C1 0.020(5) 0.022(4) 0.035(5) 0.013(4) 0.006(4) 0.012(4) C2 0.030(6) 0.023(5) 0.035(5) 0.011(4) 0.012(5) 0.011(4) C3 0.032(6) 0.020(5) 0.039(5) 0.012(5) 0.016(5) 0.009(4) C4 0.027(6) 0.025(5) 0.040(5) 0.010(5) 0.013(5) 0.005(4) C5 0.030(6) 0.020(5) 0.034(5) 0.009(4) 0.011(5) 0.007(4) C6 0.021(5) 0.020(4) 0.031(4) 0.011(4) 0.011(4) 0.011(4) C7 0.024(6) 0.025(5) 0.031(5) 0.005(4) 0.009(4) 0.008(4) C8 0.021(5) 0.027(5) 0.034(5) 0.003(4) 0.009(5) 0.004(4) C9 0.027(6) 0.023(5) 0.040(5) 0.014(4) 0.013(5) 0.006(4) C10 0.033(6) 0.025(5) 0.032(5) 0.011(4) 0.008(5) 0.013(4) C11 0.024(5) 0.012(4) 0.029(5) 0.010(4) 0.005(4) 0.005(4) C12 0.025(5) 0.014(4) 0.029(5) 0.003(4) 0.012(4) 0.007(4) C13 0.024(5) 0.019(4) 0.027(5) 0.010(4) 0.012(4) 0.010(4) C14 0.029(6) 0.013(4) 0.031(5) 0.009(4) 0.005(4) 0.007(4) C15 0.030(5) 0.026(5) 0.028(5) 0.011(4) 0.014(4) 0.017(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' 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' 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 O3 Cu1 O3 180.0 . 2_666 ? O3 Cu1 N5 97.2(3) . 2_666 ? O3 Cu1 N5 82.8(3) 2_666 2_666 ? O3 Cu1 N5 82.8(3) . . ? O3 Cu1 N5 97.2(3) 2_666 . ? N5 Cu1 N5 180.0 2_666 . ? N4 Cu2 N1 168.6(4) . . ? N4 Cu2 N2 101.9(4) . . ? N1 Cu2 N2 87.8(4) . . ? N4 Cu2 O5 88.5(4) . . ? N1 Cu2 O5 92.2(4) . . ? N2 Cu2 O5 116.9(4) . . ? N4 Cu2 O1 79.5(3) . . ? N1 Cu2 O1 90.7(3) . . ? N2 Cu2 O1 120.3(4) . . ? O5 Cu2 O1 122.8(4) . . ? C14 O1 Cu2 114.5(6) . . ? C15 O3 Cu1 114.5(6) . . ? Cu2 O5 H6 99(7) . . ? Cu2 O5 H1 99(7) . . ? H6 O5 H1 103(5) . . ? H11 O6 H13 112.89(19) . . ? C1 N1 C5 119.2(10) . . ? C1 N1 Cu2 124.7(9) . . ? C5 N1 Cu2 115.6(8) . . ? C6 N2 C10 116.9(12) . . ? C6 N2 Cu2 124.8(8) . . ? C10 N2 Cu2 116.6(8) . . ? C1 N3 C6 131.4(11) . . ? C1 N3 H3 114.3 . . ? C6 N3 H3 114.3 . . ? N5 N4 C11 107.1(8) . . ? N5 N4 Cu2 137.9(7) . . ? C11 N4 Cu2 114.6(7) . . ? C13 N5 N4 108.0(8) . . ? C13 N5 Cu1 110.7(7) . . ? N4 N5 Cu1 140.3(7) . . ? N1 C1 N3 121.3(10) . . ? N1 C1 C2 120.3(12) . . ? N3 C1 C2 118.4(12) . . ? C3 C2 C1 120.1(12) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.2(11) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C5 C4 C3 118.7(13) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 N1 122.4(13) . . ? C4 C5 H5 118.8 . . ? N1 C5 H5 118.8 . . ? N2 C6 C7 122.7(11) . . ? N2 C6 N3 118.1(12) . . ? C7 C6 N3 119.2(11) . . ? C8 C7 C6 119.3(12) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 119.6(14) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 119.5(12) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 N2 121.8(12) . . ? C9 C10 H10 119.1 . . ? N2 C10 H10 119.1 . . ? C12 C11 N4 110.4(9) . . ? C12 C11 C14 134.2(10) . . ? N4 C11 C14 115.3(9) . . ? C11 C12 C13 104.8(9) . . ? C11 C12 H12 127.6 . . ? C13 C12 H12 127.6 . . ? N5 C13 C12 109.8(9) . . ? N5 C13 C15 117.3(9) . . ? C12 C13 C15 132.9(10) . . ? O2 C14 O1 125.8(10) . . ? O2 C14 C11 118.6(10) . . ? O1 C14 C11 115.5(9) . . ? O4 C15 O3 123.9(10) . . ? O4 C15 C13 121.7(10) . . ? O3 C15 C13 114.3(9) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.989(7) . ? Cu1 O3 1.989(7) 2_666 ? Cu1 N5 2.003(9) 2_666 ? Cu1 N5 2.003(9) . ? Cu2 N4 1.997(9) . ? Cu2 N1 2.018(9) . ? Cu2 N2 2.044(11) . ? Cu2 O5 2.088(10) . ? Cu2 O1 2.111(8) . ? O1 C14 1.269(14) . ? O2 C14 1.244(13) . ? O3 C15 1.300(13) . ? O4 C15 1.228(13) . ? O5 H6 0.84(2) . ? O5 H1 0.85(2) . ? O6 H11 0.9000(11) . ? O6 H13 0.9000(11) . ? N1 C1 1.336(16) . ? N1 C5 1.353(16) . ? N2 C6 1.349(15) . ? N2 C10 1.369(15) . ? N3 C1 1.343(16) . ? N3 C6 1.414(14) . ? N3 H3 0.8600 . ? N4 N5 1.355(12) . ? N4 C11 1.362(14) . ? N5 C13 1.339(14) . ? C1 C2 1.396(16) . ? C2 C3 1.347(18) . ? C2 H2 0.9300 . ? C3 C4 1.396(18) . ? C3 H3A 0.9300 . ? C4 C5 1.349(16) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.367(18) . ? C7 C8 1.345(17) . ? C7 H7 0.9300 . ? C8 C9 1.374(18) . ? C8 H8 0.9300 . ? C9 C10 1.356(18) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.350(15) . ? C11 C14 1.495(15) . ? C12 C13 1.389(15) . ? C12 H12 0.9300 . ? C13 C15 1.490(15) . ?