# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 # Attachment 'data_1.cif' data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Henryk Kozlowski' _publ_contact_author_address ; Faculty of Chemistry University of Wroclaw F Joliot-Curie 14 Wroclaw 50-383 POLAND ; _publ_contact_author_email HENRYKOZ@WCHUWR.CHEM.UNI.WROC.PL _publ_section_title ; Efficient Stabilization of Copper(III) in Tetraaza Pseudo-macrocyclic Oxime-and-Hydrazide Ligands with adjustable cavity size ; loop_ _publ_author_name I.O.Fritsky H.Kozlowski O.M.Kanderal M.Haukka, ; J.Swiatek-Kozlowska ; E.Gumienna-Kontecka F.Meyer data_1 _database_code_depnum_ccdc_archive 'CCDC 610646' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetraphenylphosphonium (N,N'-bis(2-Hydroxyiminopropionyl) propane-1,3-diamine)-cuprate(II) tetrahemyhydrate ; _chemical_name_common ; tetraphenylphosphonium (N,N'-bis(2-Hydroxyiminopropionyl) propane-1,3-diamine)-cuprate(ii) tetrahemyhydrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H42 Cu N4 O8.50 P' _chemical_formula_weight 725.22 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' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2410(6) _cell_length_b 12.6521(7) _cell_length_c 13.0200(7) _cell_angle_alpha 78.2820(10) _cell_angle_beta 85.7610(10) _cell_angle_gamma 68.6370(10) _cell_volume 1688.56(16) _cell_formula_units_Z 2 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour 'carrot red' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.752 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9960 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 30.51 _reflns_number_total 9960 _reflns_number_gt 7857 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+1.3015P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9960 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.44290(2) 0.136034(19) 0.918530(18) 0.02019(7) Uani 1 1 d . . . P1 P 0.32027(4) 0.37288(4) 0.42927(4) 0.02090(10) Uani 1 1 d . . . O1 O 0.19548(13) 0.27871(12) 0.99514(12) 0.0282(3) Uani 1 1 d . . . O2 O 0.22957(13) 0.10600(13) 0.70377(12) 0.0291(3) Uani 1 1 d . . . O3 O 0.80446(12) 0.04086(12) 1.00409(11) 0.0248(3) Uani 1 1 d . . . O4 O 0.38980(13) 0.27210(12) 1.08412(12) 0.0264(3) Uani 1 1 d . . . O1W O 0.02438(16) 0.89309(14) 0.90869(14) 0.0319(3) Uani 1 1 d . . . O2W O 0.02431(16) 0.02907(15) 0.70010(16) 0.0345(4) Uani 1 1 d . . . O3W O 0.3923(2) 0.4864(2) 0.9675(2) 0.0488(5) Uani 1 1 d . . . O4W O 0.1360(3) 0.6399(2) 0.9336(2) 0.0667(7) Uani 1 1 d . . . O5W O -0.0121(5) 0.4921(4) 0.9571(4) 0.0741(15) Uani 0.50 1 d P . . N1 N 0.25836(15) 0.21271(13) 0.92262(13) 0.0219(3) Uani 1 1 d . . . N2 N 0.40273(15) 0.08939(14) 0.79918(13) 0.0230(3) Uani 1 1 d . . . N3 N 0.62401(14) 0.05972(14) 0.91779(13) 0.0226(3) Uani 1 1 d . . . N4 N 0.48031(14) 0.19701(13) 1.03267(13) 0.0211(3) Uani 1 1 d . . . C1 C 0.05379(18) 0.2429(2) 0.84234(19) 0.0317(4) Uani 1 1 d . . . H1A H 0.0206 0.1804 0.8669 0.048 Uiso 1 1 calc R . . H1B H 0.0309 0.2757 0.7685 0.048 Uiso 1 1 calc R . . H1C H 0.0166 0.3033 0.8843 0.048 Uiso 1 1 calc R . . C2 C 0.19487(17) 0.19641(16) 0.85347(16) 0.0231(4) Uani 1 1 d . . . C3 C 0.27984(18) 0.12415(16) 0.77772(15) 0.0224(4) Uani 1 1 d . . . C4 C 0.49690(18) 0.02433(17) 0.72999(16) 0.0248(4) Uani 1 1 d . . . H4A H 0.4637 0.0499 0.6573 0.030 Uiso 1 1 calc R . . H4B H 0.5105 -0.0589 0.7518 0.030 Uiso 1 1 calc R . . C5 C 0.62377(18) 0.04127(17) 0.73276(15) 0.0236(4) Uani 1 1 d . . . H5A H 0.6805 0.0035 0.6786 0.028 Uiso 1 1 calc R . . H5B H 0.6082 0.1250 0.7135 0.028 Uiso 1 1 calc R . . C6 C 0.69352(17) -0.00556(16) 0.83738(16) 0.0235(4) Uani 1 1 d . . . H6A H 0.7035 -0.0879 0.8606 0.028 Uiso 1 1 calc R . . H6B H 0.7799 -0.0011 0.8286 0.028 Uiso 1 1 calc R . . C7 C 0.68554(16) 0.07946(14) 0.98972(15) 0.0192(3) Uani 1 1 d . . . C8 C 0.59918(17) 0.15988(15) 1.05824(15) 0.0200(3) Uani 1 1 d . . . C9 C 0.64950(19) 0.19302(18) 1.14422(17) 0.0280(4) Uani 1 1 d . . . H9A H 0.6909 0.2485 1.1143 0.042 Uiso 1 1 calc R . . H9B H 0.7119 0.1240 1.1854 0.042 Uiso 1 1 calc R . . H9C H 0.5789 0.2284 1.1897 0.042 Uiso 1 1 calc R . . C10 C 0.28943(18) 0.39339(15) 0.56244(15) 0.0232(4) Uani 1 1 d . . . C11 C 0.1642(2) 0.44268(19) 0.59602(18) 0.0339(5) Uani 1 1 d . . . H11 H 0.0949 0.4566 0.5513 0.041 Uiso 1 1 calc R . . C12 C 0.1410(2) 0.47122(19) 0.6943(2) 0.0400(5) Uani 1 1 d . . . H12 H 0.0556 0.5053 0.7170 0.048 Uiso 1 1 calc R . . C13 C 0.2415(3) 0.4505(2) 0.75993(19) 0.0405(6) Uani 1 1 d . . . H13 H 0.2252 0.4718 0.8269 0.049 Uiso 1 1 calc R . . C14 C 0.3652(3) 0.3989(2) 0.72806(19) 0.0377(5) Uani 1 1 d . . . H14 H 0.4339 0.3827 0.7742 0.045 Uiso 1 1 calc R . . C15 C 0.3905(2) 0.37037(17) 0.62964(17) 0.0274(4) Uani 1 1 d . . . H15 H 0.4761 0.3353 0.6080 0.033 Uiso 1 1 calc R . . C16 C 0.21756(17) 0.30537(16) 0.39367(16) 0.0228(4) Uani 1 1 d . . . C17 C 0.1675(2) 0.23970(18) 0.47139(18) 0.0303(4) Uani 1 1 d . . . H17 H 0.1857 0.2322 0.5432 0.036 Uiso 1 1 calc R . . C18 C 0.0908(2) 0.18531(19) 0.4432(2) 0.0347(5) Uani 1 1 d . . . H18 H 0.0560 0.1409 0.4958 0.042 Uiso 1 1 calc R . . C19 C 0.0649(2) 0.19571(18) 0.33861(19) 0.0327(5) Uani 1 1 d . . . H19 H 0.0124 0.1585 0.3197 0.039 Uiso 1 1 calc R . . C20 C 0.1152(2) 0.26024(19) 0.26149(18) 0.0308(4) Uani 1 1 d . . . H20 H 0.0972 0.2671 0.1898 0.037 Uiso 1 1 calc R . . C21 C 0.19184(19) 0.31499(18) 0.28836(17) 0.0278(4) Uani 1 1 d . . . H21 H 0.2267 0.3589 0.2352 0.033 Uiso 1 1 calc R . . C22 C 0.29339(18) 0.51164(16) 0.34640(16) 0.0237(4) Uani 1 1 d . . . C23 C 0.2325(2) 0.61235(17) 0.38646(18) 0.0298(4) Uani 1 1 d . . . H23 H 0.2065 0.6075 0.4578 0.036 Uiso 1 1 calc R . . C24 C 0.2100(2) 0.71989(18) 0.32194(19) 0.0340(5) Uani 1 1 d . . . H24 H 0.1686 0.7886 0.3491 0.041 Uiso 1 1 calc R . . C25 C 0.2479(2) 0.72624(19) 0.21852(19) 0.0334(5) Uani 1 1 d . . . H25 H 0.2318 0.7996 0.1743 0.040 Uiso 1 1 calc R . . C26 C 0.3091(2) 0.6268(2) 0.17849(19) 0.0354(5) Uani 1 1 d . . . H26 H 0.3347 0.6324 0.1070 0.042 Uiso 1 1 calc R . . C27 C 0.3333(2) 0.51903(18) 0.24201(18) 0.0314(4) Uani 1 1 d . . . H27 H 0.3767 0.4508 0.2147 0.038 Uiso 1 1 calc R . . C28 C 0.48423(17) 0.28472(16) 0.41795(16) 0.0222(4) Uani 1 1 d . . . C29 C 0.52054(18) 0.16467(16) 0.43862(16) 0.0250(4) Uani 1 1 d . . . H29 H 0.4578 0.1297 0.4527 0.030 Uiso 1 1 calc R . . C30 C 0.6494(2) 0.09668(17) 0.43848(18) 0.0297(4) Uani 1 1 d . . . H30 H 0.6749 0.0148 0.4525 0.036 Uiso 1 1 calc R . . C31 C 0.74070(19) 0.14743(19) 0.41813(18) 0.0312(4) Uani 1 1 d . . . H31 H 0.8287 0.1003 0.4191 0.037 Uiso 1 1 calc R . . C32 C 0.7049(2) 0.2664(2) 0.3964(2) 0.0353(5) Uani 1 1 d . . . H32 H 0.7681 0.3008 0.3812 0.042 Uiso 1 1 calc R . . C33 C 0.5764(2) 0.33575(18) 0.39680(19) 0.0317(5) Uani 1 1 d . . . H33 H 0.5516 0.4175 0.3827 0.038 Uiso 1 1 calc R . . H1O H 0.267(4) 0.286(3) 1.030(3) 0.080(11) Uiso 1 1 d . . . H5O1 H 0.077(3) 0.912(3) 0.938(3) 0.069(11) Uiso 1 1 d . . . H5O2 H -0.039(3) 0.929(3) 0.933(3) 0.057(10) Uiso 1 1 d . . . H6O1 H 0.019(3) -0.007(3) 0.758(3) 0.057(10) Uiso 1 1 d . . . H6O2 H 0.079(3) 0.056(3) 0.701(3) 0.068(11) Uiso 1 1 d . . . H7O1 H 0.387(3) 0.426(3) 0.997(3) 0.061(11) Uiso 1 1 d . . . H7O2 H 0.408(7) 0.500(7) 0.985(6) 0.17(4) Uiso 1 1 d . . . H8O1 H 0.1961 0.5987 0.9488 0.25(4) Uiso 1 1 d . . . H8O2 H 0.109(3) 0.695(3) 0.929(3) 0.049(10) Uiso 1 1 d . . . H9O1 H 0.0668 0.4276 0.9675 0.22(6) Uiso 0.50 1 d P . . H9O2 H 0.0046 0.5430 0.9713 0.050 Uiso 0.50 1 d P . . 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 0.01632(10) 0.02192(11) 0.02056(13) -0.00621(9) -0.00100(8) -0.00343(8) P1 0.0195(2) 0.0198(2) 0.0215(3) -0.00416(18) -0.00134(17) -0.00443(16) O1 0.0222(7) 0.0302(7) 0.0296(8) -0.0122(6) 0.0041(6) -0.0037(5) O2 0.0261(7) 0.0392(8) 0.0240(8) -0.0062(6) -0.0042(6) -0.0131(6) O3 0.0171(6) 0.0289(7) 0.0280(8) -0.0085(6) -0.0013(5) -0.0058(5) O4 0.0214(6) 0.0273(7) 0.0294(8) -0.0141(6) 0.0039(5) -0.0038(5) O1W 0.0225(7) 0.0358(8) 0.0404(10) -0.0153(7) 0.0011(7) -0.0098(6) O2W 0.0296(8) 0.0335(8) 0.0423(11) -0.0103(8) -0.0026(7) -0.0115(7) O3W 0.0564(12) 0.0369(10) 0.0573(14) -0.0041(9) -0.0099(10) -0.0224(9) O4W 0.0799(17) 0.0339(11) 0.0816(18) -0.0187(11) -0.0124(13) -0.0082(12) O5W 0.045(2) 0.059(3) 0.105(5) -0.012(3) 0.001(3) -0.005(2) N1 0.0198(7) 0.0211(7) 0.0211(8) -0.0031(6) 0.0013(6) -0.0034(6) N2 0.0207(7) 0.0281(8) 0.0204(8) -0.0076(6) 0.0000(6) -0.0076(6) N3 0.0173(7) 0.0255(7) 0.0233(9) -0.0098(6) -0.0006(6) -0.0030(6) N4 0.0202(7) 0.0210(7) 0.0208(8) -0.0067(6) 0.0025(6) -0.0050(6) C1 0.0186(9) 0.0391(11) 0.0345(12) -0.0067(9) -0.0019(8) -0.0066(8) C2 0.0197(8) 0.0227(8) 0.0236(10) 0.0007(7) -0.0014(7) -0.0062(7) C3 0.0237(9) 0.0231(8) 0.0193(10) 0.0005(7) -0.0016(7) -0.0093(7) C4 0.0244(9) 0.0315(9) 0.0198(10) -0.0094(8) 0.0012(7) -0.0094(7) C5 0.0229(9) 0.0272(9) 0.0201(10) -0.0060(7) 0.0018(7) -0.0078(7) C6 0.0187(8) 0.0261(8) 0.0232(10) -0.0105(7) 0.0012(7) -0.0022(7) C7 0.0188(8) 0.0178(7) 0.0188(9) -0.0014(6) 0.0004(6) -0.0050(6) C8 0.0215(8) 0.0202(8) 0.0183(9) -0.0033(7) -0.0001(7) -0.0077(6) C9 0.0254(9) 0.0356(10) 0.0266(11) -0.0122(8) 0.0002(8) -0.0119(8) C10 0.0259(9) 0.0204(8) 0.0204(10) -0.0033(7) -0.0015(7) -0.0051(7) C11 0.0285(10) 0.0345(11) 0.0302(12) -0.0055(9) -0.0007(9) -0.0017(8) C12 0.0444(13) 0.0300(10) 0.0362(14) -0.0099(10) 0.0117(10) -0.0028(9) C13 0.0676(17) 0.0345(11) 0.0247(12) -0.0095(9) 0.0074(11) -0.0237(11) C14 0.0542(14) 0.0431(12) 0.0253(12) -0.0044(9) -0.0055(10) -0.0288(11) C15 0.0302(10) 0.0289(9) 0.0249(11) -0.0016(8) -0.0044(8) -0.0135(8) C16 0.0190(8) 0.0219(8) 0.0259(10) -0.0057(7) -0.0015(7) -0.0047(6) C17 0.0331(10) 0.0321(10) 0.0252(11) 0.0004(8) -0.0050(8) -0.0131(8) C18 0.0320(11) 0.0328(10) 0.0406(14) -0.0022(9) -0.0001(9) -0.0155(9) C19 0.0242(9) 0.0315(10) 0.0462(14) -0.0179(10) -0.0001(9) -0.0088(8) C20 0.0266(10) 0.0357(10) 0.0320(12) -0.0156(9) -0.0016(8) -0.0082(8) C21 0.0274(9) 0.0322(10) 0.0246(11) -0.0085(8) 0.0020(8) -0.0104(8) C22 0.0222(8) 0.0223(8) 0.0251(10) -0.0025(7) -0.0024(7) -0.0069(7) C23 0.0317(10) 0.0245(9) 0.0286(12) -0.0040(8) -0.0029(8) -0.0048(8) C24 0.0333(11) 0.0228(9) 0.0413(14) -0.0035(9) -0.0043(9) -0.0050(8) C25 0.0316(11) 0.0298(10) 0.0365(13) 0.0051(9) -0.0076(9) -0.0131(8) C26 0.0382(12) 0.0394(11) 0.0292(12) 0.0008(9) 0.0011(9) -0.0187(10) C27 0.0331(11) 0.0304(10) 0.0304(12) -0.0063(9) 0.0040(9) -0.0115(8) C28 0.0202(8) 0.0224(8) 0.0230(10) -0.0067(7) -0.0003(7) -0.0053(7) C29 0.0237(9) 0.0235(8) 0.0264(11) -0.0059(8) -0.0001(7) -0.0062(7) C30 0.0272(10) 0.0232(9) 0.0336(12) -0.0089(8) -0.0012(8) -0.0009(7) C31 0.0220(9) 0.0355(10) 0.0336(12) -0.0149(9) 0.0005(8) -0.0028(8) C32 0.0229(10) 0.0375(11) 0.0491(15) -0.0156(10) 0.0031(9) -0.0117(8) C33 0.0252(9) 0.0255(9) 0.0465(14) -0.0101(9) 0.0010(9) -0.0099(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N2 1.9072(16) . ? Cu1 N3 1.9094(15) . ? Cu1 N4 1.9429(16) . ? Cu1 N1 1.9457(15) . ? Cu1 N3 3.1965(17) 2_657 ? Cu1 Cu1 3.4949(5) 2_657 ? P1 C28 1.7865(19) . ? P1 C10 1.795(2) . ? P1 C22 1.7972(19) . ? P1 C16 1.7989(19) . ? O1 N1 1.371(2) . ? O1 H1O 0.99(4) . ? O2 C3 1.251(2) . ? O3 C7 1.259(2) . ? O4 N4 1.3565(19) . ? O1W H5O1 0.85(4) . ? O1W H5O2 0.77(3) . ? O2W H6O1 0.81(3) . ? O2W H6O2 0.81(4) . ? O3W H7O1 0.80(4) . ? O3W H7O2 0.40(7) . ? O4W H8O1 0.699(3) . ? O4W H8O2 0.64(3) . ? O5W O5W 1.240(10) 2_567 ? O5W H9O1 0.957(5) . ? O5W H9O2 0.792(5) . ? N1 C2 1.281(3) . ? N2 C3 1.321(2) . ? N2 C4 1.461(2) . ? N3 C7 1.317(2) . ? N3 C6 1.466(2) . ? N4 C8 1.289(2) . ? C1 C2 1.484(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.520(3) . ? C4 C5 1.521(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.521(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.515(2) . ? C8 C9 1.485(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.393(3) . ? C10 C15 1.394(3) . ? C11 C12 1.381(3) . ? C11 H11 0.9500 . ? C12 C13 1.382(4) . ? C12 H12 0.9500 . ? C13 C14 1.376(4) . ? C13 H13 0.9500 . ? C14 C15 1.383(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C21 1.394(3) . ? C16 C17 1.395(3) . ? C17 C18 1.391(3) . ? C17 H17 0.9500 . ? C18 C19 1.383(3) . ? C18 H18 0.9500 . ? C19 C20 1.384(3) . ? C19 H19 0.9500 . ? C20 C21 1.386(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.395(3) . ? C22 C27 1.395(3) . ? C23 C24 1.392(3) . ? C23 H23 0.9500 . ? C24 C25 1.377(3) . ? C24 H24 0.9500 . ? C25 C26 1.382(3) . ? C25 H25 0.9500 . ? C26 C27 1.387(3) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C33 1.392(3) . ? C28 C29 1.395(3) . ? C29 C30 1.390(3) . ? C29 H29 0.9500 . ? C30 C31 1.380(3) . ? C30 H30 0.9500 . ? C31 C32 1.382(3) . ? C31 H31 0.9500 . ? C32 C33 1.390(3) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? 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 Cu1 N3 98.54(7) . . ? N2 Cu1 N4 174.98(7) . . ? N3 Cu1 N4 83.01(7) . . ? N2 Cu1 N1 82.38(7) . . ? N3 Cu1 N1 178.74(7) . . ? N4 Cu1 N1 96.14(7) . . ? N2 Cu1 N3 93.76(6) . 2_657 ? N3 Cu1 N3 97.76(5) . 2_657 ? N4 Cu1 N3 90.74(6) . 2_657 ? N1 Cu1 N3 81.30(5) . 2_657 ? N2 Cu1 Cu1 98.11(5) . 2_657 ? N3 Cu1 Cu1 64.99(5) . 2_657 ? N4 Cu1 Cu1 86.87(5) . 2_657 ? N1 Cu1 Cu1 114.07(5) . 2_657 ? N3 Cu1 Cu1 32.77(3) 2_657 2_657 ? C28 P1 C10 108.72(9) . . ? C28 P1 C22 108.27(9) . . ? C10 P1 C22 108.26(9) . . ? C28 P1 C16 110.61(8) . . ? C10 P1 C16 109.68(9) . . ? C22 P1 C16 111.23(9) . . ? N1 O1 H1O 102(2) . . ? H5O1 O1W H5O2 100(3) . . ? H6O1 O2W H6O2 108(3) . . ? H7O1 O3W H7O2 114(10) . . ? H8O1 O4W H8O2 136(3) . . ? O5W O5W H9O1 84.7(5) 2_567 . ? O5W O5W H9O2 49.5(4) 2_567 . ? H9O1 O5W H9O2 103.8(5) . . ? C2 N1 O1 119.95(16) . . ? C2 N1 Cu1 115.99(13) . . ? O1 N1 Cu1 124.04(12) . . ? C3 N2 C4 119.58(16) . . ? C3 N2 Cu1 115.53(13) . . ? C4 N2 Cu1 124.83(12) . . ? C7 N3 C6 120.95(15) . . ? C7 N3 Cu1 114.83(12) . . ? C6 N3 Cu1 123.87(12) . . ? C8 N4 O4 121.16(16) . . ? C8 N4 Cu1 115.17(12) . . ? O4 N4 Cu1 123.67(12) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C1 126.08(19) . . ? N1 C2 C3 112.90(16) . . ? C1 C2 C3 121.01(18) . . ? O2 C3 N2 127.73(19) . . ? O2 C3 C2 119.15(17) . . ? N2 C3 C2 113.11(16) . . ? N2 C4 C5 111.60(15) . . ? N2 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N2 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C4 115.45(17) . . ? C6 C5 H5A 108.4 . . ? C4 C5 H5A 108.4 . . ? C6 C5 H5B 108.4 . . ? C4 C5 H5B 108.4 . . ? H5A C5 H5B 107.5 . . ? N3 C6 C5 111.39(15) . . ? N3 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N3 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? O3 C7 N3 126.88(17) . . ? O3 C7 C8 119.35(16) . . ? N3 C7 C8 113.75(15) . . ? N4 C8 C9 124.51(17) . . ? N4 C8 C7 113.18(16) . . ? C9 C8 C7 122.29(16) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 119.60(19) . . ? C11 C10 P1 119.91(16) . . ? C15 C10 P1 120.20(16) . . ? C12 C11 C10 120.0(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 119.9(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.7(2) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 119.5(2) . . ? C14 C15 H15 120.2 . . ? C10 C15 H15 120.2 . . ? C21 C16 C17 119.97(18) . . ? C21 C16 P1 120.09(15) . . ? C17 C16 P1 119.90(15) . . ? C18 C17 C16 119.6(2) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C19 C18 C17 120.2(2) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 120.18(19) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C21 120.3(2) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C16 119.7(2) . . ? C20 C21 H21 120.1 . . ? C16 C21 H21 120.1 . . ? C23 C22 C27 119.82(18) . . ? C23 C22 P1 119.98(16) . . ? C27 C22 P1 120.20(15) . . ? C24 C23 C22 120.0(2) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C25 C24 C23 119.7(2) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 120.6(2) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C27 120.4(2) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C26 C27 C22 119.4(2) . . ? C26 C27 H27 120.3 . . ? C22 C27 H27 120.3 . . ? C33 C28 C29 120.19(17) . . ? C33 C28 P1 119.81(14) . . ? C29 C28 P1 119.79(14) . . ? C30 C29 C28 119.35(18) . . ? C30 C29 H29 120.3 . . ? C28 C29 H29 120.3 . . ? C31 C30 C29 120.36(18) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C30 C31 C32 120.39(19) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? C31 C32 C33 120.0(2) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? C32 C33 C28 119.67(19) . . ? C32 C33 H33 120.2 . . ? C28 C33 H33 120.2 . . ? 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 N2 Cu1 N1 C2 2.79(14) . . . . ? N3 Cu1 N1 C2 -134(3) . . . . ? N4 Cu1 N1 C2 177.97(14) . . . . ? N3 Cu1 N1 C2 -92.22(14) 2_657 . . . ? Cu1 Cu1 N1 C2 -92.73(14) 2_657 . . . ? N2 Cu1 N1 O1 -178.76(15) . . . . ? N3 Cu1 N1 O1 44(3) . . . . ? N4 Cu1 N1 O1 -3.59(15) . . . . ? N3 Cu1 N1 O1 86.23(14) 2_657 . . . ? Cu1 Cu1 N1 O1 85.72(14) 2_657 . . . ? N3 Cu1 N2 C3 177.39(14) . . . . ? N4 Cu1 N2 C3 -74.9(8) . . . . ? N1 Cu1 N2 C3 -1.74(14) . . . . ? N3 Cu1 N2 C3 78.95(14) 2_657 . . . ? Cu1 Cu1 N2 C3 111.62(13) 2_657 . . . ? N3 Cu1 N2 C4 -5.45(17) . . . . ? N4 Cu1 N2 C4 102.3(7) . . . . ? N1 Cu1 N2 C4 175.42(16) . . . . ? N3 Cu1 N2 C4 -103.89(15) 2_657 . . . ? Cu1 Cu1 N2 C4 -71.22(15) 2_657 . . . ? N2 Cu1 N3 C7 176.46(14) . . . . ? N4 Cu1 N3 C7 1.27(14) . . . . ? N1 Cu1 N3 C7 -46(3) . . . . ? N3 Cu1 N3 C7 -88.53(14) 2_657 . . . ? Cu1 Cu1 N3 C7 -88.53(14) 2_657 . . . ? N2 Cu1 N3 C6 3.17(16) . . . . ? N4 Cu1 N3 C6 -172.02(16) . . . . ? N1 Cu1 N3 C6 140(3) . . . . ? N3 Cu1 N3 C6 98.19(15) 2_657 . . . ? Cu1 Cu1 N3 C6 98.19(15) 2_657 . . . ? N2 Cu1 N4 C8 -110.5(7) . . . . ? N3 Cu1 N4 C8 -2.11(14) . . . . ? N1 Cu1 N4 C8 176.96(14) . . . . ? N3 Cu1 N4 C8 95.62(14) 2_657 . . . ? Cu1 Cu1 N4 C8 63.07(13) 2_657 . . . ? N2 Cu1 N4 O4 70.3(8) . . . . ? N3 Cu1 N4 O4 178.72(15) . . . . ? N1 Cu1 N4 O4 -2.22(15) . . . . ? N3 Cu1 N4 O4 -83.55(14) 2_657 . . . ? Cu1 Cu1 N4 O4 -116.11(14) 2_657 . . . ? O1 N1 C2 C1 -0.2(3) . . . . ? Cu1 N1 C2 C1 178.36(16) . . . . ? O1 N1 C2 C3 178.39(15) . . . . ? Cu1 N1 C2 C3 -3.1(2) . . . . ? C4 N2 C3 O2 1.9(3) . . . . ? Cu1 N2 C3 O2 179.23(16) . . . . ? C4 N2 C3 C2 -176.71(16) . . . . ? Cu1 N2 C3 C2 0.6(2) . . . . ? N1 C2 C3 O2 -177.10(17) . . . . ? C1 C2 C3 O2 1.5(3) . . . . ? N1 C2 C3 N2 1.7(2) . . . . ? C1 C2 C3 N2 -179.72(17) . . . . ? C3 N2 C4 C5 152.58(17) . . . . ? Cu1 N2 C4 C5 -24.5(2) . . . . ? N2 C4 C5 C6 65.0(2) . . . . ? C7 N3 C6 C5 -144.16(17) . . . . ? Cu1 N3 C6 C5 28.7(2) . . . . ? C4 C5 C6 N3 -67.4(2) . . . . ? C6 N3 C7 O3 -5.3(3) . . . . ? Cu1 N3 C7 O3 -178.84(15) . . . . ? C6 N3 C7 C8 173.14(16) . . . . ? Cu1 N3 C7 C8 -0.4(2) . . . . ? O4 N4 C8 C9 0.4(3) . . . . ? Cu1 N4 C8 C9 -178.84(15) . . . . ? O4 N4 C8 C7 -178.41(15) . . . . ? Cu1 N4 C8 C7 2.4(2) . . . . ? O3 C7 C8 N4 177.25(16) . . . . ? N3 C7 C8 N4 -1.4(2) . . . . ? O3 C7 C8 C9 -1.6(3) . . . . ? N3 C7 C8 C9 179.85(17) . . . . ? C28 P1 C10 C11 -169.30(16) . . . . ? C22 P1 C10 C11 73.29(18) . . . . ? C16 P1 C10 C11 -48.24(19) . . . . ? C28 P1 C10 C15 16.76(18) . . . . ? C22 P1 C10 C15 -100.64(16) . . . . ? C16 P1 C10 C15 137.83(16) . . . . ? C15 C10 C11 C12 1.7(3) . . . . ? P1 C10 C11 C12 -172.26(17) . . . . ? C10 C11 C12 C13 -0.4(4) . . . . ? C11 C12 C13 C14 -1.4(4) . . . . ? C12 C13 C14 C15 1.8(3) . . . . ? C13 C14 C15 C10 -0.5(3) . . . . ? C11 C10 C15 C14 -1.3(3) . . . . ? P1 C10 C15 C14 172.67(16) . . . . ? C28 P1 C16 C21 -81.57(17) . . . . ? C10 P1 C16 C21 158.51(15) . . . . ? C22 P1 C16 C21 38.79(18) . . . . ? C28 P1 C16 C17 96.01(17) . . . . ? C10 P1 C16 C17 -23.90(18) . . . . ? C22 P1 C16 C17 -143.63(16) . . . . ? C21 C16 C17 C18 -0.8(3) . . . . ? P1 C16 C17 C18 -178.38(16) . . . . ? C16 C17 C18 C19 0.4(3) . . . . ? C17 C18 C19 C20 0.0(3) . . . . ? C18 C19 C20 C21 -0.1(3) . . . . ? C19 C20 C21 C16 -0.3(3) . . . . ? C17 C16 C21 C20 0.8(3) . . . . ? P1 C16 C21 C20 178.35(15) . . . . ? C28 P1 C22 C23 -129.83(17) . . . . ? C10 P1 C22 C23 -12.14(19) . . . . ? C16 P1 C22 C23 108.43(17) . . . . ? C28 P1 C22 C27 50.12(19) . . . . ? C10 P1 C22 C27 167.81(16) . . . . ? C16 P1 C22 C27 -71.61(18) . . . . ? C27 C22 C23 C24 1.0(3) . . . . ? P1 C22 C23 C24 -179.05(16) . . . . ? C22 C23 C24 C25 0.1(3) . . . . ? C23 C24 C25 C26 -0.6(3) . . . . ? C24 C25 C26 C27 0.0(3) . . . . ? C25 C26 C27 C22 1.1(3) . . . . ? C23 C22 C27 C26 -1.6(3) . . . . ? P1 C22 C27 C26 178.47(17) . . . . ? C10 P1 C28 C33 -87.25(19) . . . . ? C22 P1 C28 C33 30.2(2) . . . . ? C16 P1 C28 C33 152.26(17) . . . . ? C10 P1 C28 C29 87.62(17) . . . . ? C22 P1 C28 C29 -154.98(16) . . . . ? C16 P1 C28 C29 -32.87(19) . . . . ? C33 C28 C29 C30 0.4(3) . . . . ? P1 C28 C29 C30 -174.47(16) . . . . ? C28 C29 C30 C31 0.0(3) . . . . ? C29 C30 C31 C32 -0.8(3) . . . . ? C30 C31 C32 C33 1.1(4) . . . . ? C31 C32 C33 C28 -0.7(4) . . . . ? C29 C28 C33 C32 0.0(3) . . . . ? P1 C28 C33 C32 174.82(18) . . . . ? 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 O1 H1O O4 0.99(4) 1.54(4) 2.514(2) 169(3) . _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.520 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.070 # Attachment 'data_2A.cif' data_2a _database_code_depnum_ccdc_archive 'CCDC 610647' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis{lithium (N,N'-bis(2-Hydroxyiminopropionyl)propane-1,3-diamine)- cuprate(II)} monohydrate formaldehyde solvate ; _chemical_name_common ; bis(lithium (N,N'-bis(2-Hydroxyiminopropionyl)propane-1,3- diamine)-cuprate(ii)) monohydrate formaldehyde solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C19 H30 Cu2 Li2 N12 O12' _chemical_formula_sum 'C19 H30 Cu2 Li2 N12 O12' _chemical_formula_weight 759.51 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' Li Li -0.0003 0.0001 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.0247(6) _cell_length_b 11.6299(6) _cell_length_c 18.2082(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.669(3) _cell_angle_gamma 90.00 _cell_volume 3031.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8417 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.68 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 1.481 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8062 _exptl_absorpt_correction_T_max 0.8844 _exptl_absorpt_process_details 'Xprep in Shelxtl v.6.14-1 (Sheldrick, 2005)' _publ_section_exptl_refinement ; The OH hydrogens were located from the difference Fourier map but constrained to ride on their parent atom (U~iso~ = 1.5 (parent atom)). Other hydrogens were positioned geometrically and allowed to ride on their parent atoms, with C---H = 0.98-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~ (parent atom). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18356 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 25.67 _reflns_number_total 5717 _reflns_number_gt 4168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1 (Crystal Impact GbR, 2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0376P)^2^+5.3678P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5717 _refine_ls_number_parameters 428 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1A Cu 0.87904(3) 0.03261(4) 0.05031(3) 0.01804(13) Uani 1 1 d . . . Cu1B Cu 0.66559(3) 0.15829(4) 0.14279(3) 0.01879(13) Uani 1 1 d . . . O1A O 0.87531(19) 0.1307(2) -0.10140(15) 0.0233(6) Uani 1 1 d . . . H1A H 0.8618 0.0520 -0.1049 0.035 Uiso 1 1 d . . . O2A O 0.99473(19) 0.3357(2) 0.12862(15) 0.0248(6) Uani 1 1 d . . . O3A O 0.8944(2) -0.2743(2) 0.14628(16) 0.0246(6) Uani 1 1 d . . . O4A O 0.83826(19) -0.0933(2) -0.09367(14) 0.0217(6) Uani 1 1 d . . . O5A O 0.81312(17) 0.1049(2) 0.21013(15) 0.0191(6) Uani 1 1 d . . . O1B O 0.7227(2) 0.2838(2) 0.02176(16) 0.0293(7) Uani 1 1 d . . . H1B H 0.7243 0.1987 0.0110 0.044 Uiso 1 1 d . . . O2B O 0.5922(2) 0.4696(3) 0.19139(17) 0.0328(7) Uani 1 1 d . . . O3B O 0.52023(19) -0.1274(2) 0.14266(17) 0.0261(7) Uani 1 1 d . . . O4B O 0.70345(18) 0.0598(2) 0.01002(15) 0.0223(6) Uani 1 1 d . . . O5B O 0.70169(18) 0.1158(2) 0.33378(16) 0.0237(6) Uani 1 1 d . . . N1A N 0.8981(2) 0.1473(3) -0.02261(17) 0.0187(7) Uani 1 1 d . . . N2A N 0.9338(2) 0.1531(3) 0.12084(17) 0.0186(7) Uani 1 1 d . . . N3A N 0.8776(2) -0.0782(3) 0.12651(17) 0.0174(7) Uani 1 1 d . . . N4A N 0.8562(2) -0.1010(3) -0.01657(17) 0.0178(7) Uani 1 1 d . . . N5A N 0.9660(2) 0.1444(3) 0.20414(17) 0.0180(7) Uani 1 1 d . . . N6A N 0.9120(2) -0.0585(3) 0.20888(17) 0.0171(7) Uani 1 1 d . . . N1B N 0.6900(2) 0.2909(3) 0.08455(19) 0.0236(8) Uani 1 1 d . . . N2B N 0.6430(2) 0.2804(3) 0.20602(18) 0.0201(7) Uani 1 1 d . . . N3B N 0.5998(2) 0.0433(3) 0.17939(19) 0.0217(7) Uani 1 1 d . . . N4B N 0.6617(2) 0.0420(3) 0.06493(18) 0.0200(7) Uani 1 1 d . . . N5B N 0.5972(2) 0.2642(3) 0.26465(18) 0.0201(7) Uani 1 1 d . . . N6B N 0.5583(2) 0.0561(3) 0.24058(19) 0.0215(7) Uani 1 1 d . . . C1A C 0.9287(3) 0.3517(4) -0.0412(2) 0.0247(9) Uani 1 1 d . . . H1AA H 0.9714 0.3385 -0.0717 0.037 Uiso 1 1 calc R . . H1AB H 0.9512 0.4167 -0.0062 0.037 Uiso 1 1 calc R . . H1AC H 0.8661 0.3690 -0.0757 0.037 Uiso 1 1 calc R . . C2A C 0.9247(2) 0.2476(3) 0.0042(2) 0.0168(8) Uani 1 1 d . . . C3A C 0.9543(3) 0.2504(3) 0.0926(2) 0.0184(8) Uani 1 1 d . . . C4A C 0.8912(3) 0.1801(3) 0.2346(2) 0.0194(8) Uani 1 1 d . . . H4AB H 0.9147 0.1808 0.2917 0.023 Uiso 1 1 calc R . . H4AA H 0.8715 0.2592 0.2170 0.023 Uiso 1 1 calc R . . C5A C 0.8386(3) -0.0104(3) 0.2371(2) 0.0190(8) Uani 1 1 d . . . H5AA H 0.7827 -0.0602 0.2202 0.023 Uiso 1 1 calc R . . H5AB H 0.8603 -0.0103 0.2942 0.023 Uiso 1 1 calc R . . C6A C 0.9912(3) 0.0239(3) 0.2263(2) 0.0187(8) Uani 1 1 d . . . H6AB H 1.0238 0.0214 0.2824 0.022 Uiso 1 1 calc R . . H6AA H 1.0360 -0.0024 0.1996 0.022 Uiso 1 1 calc R . . C7A C 0.8772(3) -0.1871(3) 0.1043(2) 0.0176(8) Uani 1 1 d . . . C8A C 0.8529(3) -0.1983(3) 0.0171(2) 0.0189(8) Uani 1 1 d . . . C9A C 0.8279(3) -0.3107(3) -0.0229(2) 0.0238(9) Uani 1 1 d . . . H9AA H 0.7620 -0.3096 -0.0541 0.036 Uiso 1 1 calc R . . H9AB H 0.8380 -0.3724 0.0154 0.036 Uiso 1 1 calc R . . H9AC H 0.8671 -0.3240 -0.0564 0.036 Uiso 1 1 calc R . . C1B C 0.6804(5) 0.5012(4) 0.0693(3) 0.0577(17) Uani 1 1 d . . . H1BB H 0.7433 0.5324 0.0927 0.087 Uiso 1 1 calc R . . H1BC H 0.6340 0.5554 0.0768 0.087 Uiso 1 1 calc R . . H1BA H 0.6698 0.4893 0.0140 0.087 Uiso 1 1 calc R . . C2B C 0.6716(3) 0.3893(4) 0.1064(3) 0.0292(10) Uani 1 1 d . . . C3B C 0.6320(3) 0.3826(3) 0.1746(2) 0.0241(9) Uani 1 1 d . . . C4B C 0.6646(3) 0.2275(3) 0.3369(2) 0.0224(9) Uani 1 1 d . . . H4BB H 0.7167 0.2834 0.3512 0.027 Uiso 1 1 calc R . . H4BA H 0.6339 0.2288 0.3780 0.027 Uiso 1 1 calc R . . C5B C 0.6276(3) 0.0339(4) 0.3147(2) 0.0244(9) Uani 1 1 d . . . H5BB H 0.5964 0.0346 0.3554 0.029 Uiso 1 1 calc R . . H5BA H 0.6542 -0.0438 0.3139 0.029 Uiso 1 1 calc R . . C6B C 0.5242(3) 0.1748(3) 0.2408(2) 0.0199(8) Uani 1 1 d . . . H6BB H 0.4851 0.1783 0.2757 0.024 Uiso 1 1 calc R . . H6BA H 0.4836 0.1934 0.1882 0.024 Uiso 1 1 calc R . . C7B C 0.5732(3) -0.0495(3) 0.1350(2) 0.0193(8) Uani 1 1 d . . . C8B C 0.6161(3) -0.0502(3) 0.0691(2) 0.0208(9) Uani 1 1 d . . . C9B C 0.6011(3) -0.1513(4) 0.0161(2) 0.0291(10) Uani 1 1 d . . . H9BA H 0.5552 -0.1314 -0.0333 0.044 Uiso 1 1 calc R . . H9BB H 0.5779 -0.2163 0.0392 0.044 Uiso 1 1 calc R . . H9BC H 0.6603 -0.1724 0.0075 0.044 Uiso 1 1 calc R . . Li1A Li 1.0717(5) 0.2718(6) 0.2405(4) 0.0229(14) Uani 1 1 d . . . Li1B Li 0.5550(5) 0.4366(6) 0.2876(4) 0.0274(16) Uani 1 1 d . . . C1F C 1.2727(4) 0.2093(5) 0.2623(3) 0.0564(16) Uani 1 1 d . . . H1FB H 1.2847 0.2104 0.3166 0.068 Uiso 1 1 calc R . . H1FA H 1.3215 0.1916 0.2411 0.068 Uiso 1 1 calc R . . O1F O 1.18196(19) 0.2339(3) 0.21304(16) 0.0273(7) Uani 1 1 d . . . O1W O 0.64976(19) 0.5151(3) 0.36454(16) 0.0280(7) Uani 1 1 d . . . H1WB H 0.6598 0.4826 0.4094 0.042 Uiso 1 1 d . . . H1WA H 0.7137 0.5377 0.3632 0.042 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 Cu1A 0.0249(3) 0.0174(2) 0.0127(2) -0.00071(19) 0.00690(19) -0.0011(2) Cu1B 0.0209(3) 0.0194(3) 0.0195(3) -0.0007(2) 0.0114(2) -0.0001(2) O1A 0.0308(16) 0.0270(15) 0.0129(14) -0.0021(11) 0.0080(12) -0.0030(12) O2A 0.0298(15) 0.0236(15) 0.0191(14) -0.0024(12) 0.0047(12) -0.0090(13) O3A 0.0341(16) 0.0193(15) 0.0220(15) 0.0015(12) 0.0108(13) 0.0024(13) O4A 0.0281(15) 0.0244(15) 0.0131(14) -0.0010(11) 0.0069(12) 0.0033(12) O5A 0.0185(13) 0.0180(14) 0.0222(15) -0.0001(11) 0.0083(12) 0.0005(11) O1B 0.0408(18) 0.0308(17) 0.0262(16) 0.0014(13) 0.0251(14) 0.0001(14) O2B 0.0494(19) 0.0221(16) 0.0338(17) 0.0015(13) 0.0232(15) 0.0091(15) O3B 0.0275(15) 0.0221(15) 0.0319(17) -0.0031(13) 0.0139(14) -0.0055(13) O4B 0.0230(14) 0.0306(16) 0.0177(14) 0.0010(12) 0.0126(12) 0.0020(12) O5B 0.0217(14) 0.0240(15) 0.0245(15) -0.0002(12) 0.0055(13) 0.0014(12) N1A 0.0202(17) 0.0269(19) 0.0097(15) -0.0010(14) 0.0056(13) -0.0001(15) N2A 0.0235(17) 0.0221(17) 0.0118(16) 0.0020(14) 0.0077(14) -0.0032(14) N3A 0.0206(17) 0.0193(17) 0.0130(16) -0.0012(13) 0.0061(14) 0.0009(14) N4A 0.0187(16) 0.0231(18) 0.0112(16) -0.0005(14) 0.0039(14) 0.0037(14) N5A 0.0197(16) 0.0221(17) 0.0133(16) -0.0005(14) 0.0065(14) -0.0018(14) N6A 0.0190(16) 0.0206(17) 0.0123(16) 0.0006(13) 0.0057(14) 0.0002(13) N1B 0.0274(19) 0.0273(19) 0.0211(18) 0.0000(15) 0.0147(16) 0.0024(15) N2B 0.0225(17) 0.0214(18) 0.0202(17) 0.0011(14) 0.0124(15) -0.0007(14) N3B 0.0239(17) 0.0237(18) 0.0234(18) -0.0004(15) 0.0160(15) 0.0006(15) N4B 0.0188(16) 0.0245(18) 0.0177(17) -0.0006(14) 0.0070(14) 0.0008(15) N5B 0.0206(17) 0.0244(18) 0.0185(17) -0.0027(14) 0.0106(14) -0.0031(14) N6B 0.0255(18) 0.0243(19) 0.0203(18) -0.0005(14) 0.0151(15) -0.0004(15) C1A 0.027(2) 0.024(2) 0.023(2) 0.0016(18) 0.0080(18) -0.0055(18) C2A 0.0142(18) 0.021(2) 0.0163(19) 0.0005(16) 0.0063(16) -0.0014(16) C3A 0.0148(18) 0.024(2) 0.018(2) -0.0033(17) 0.0074(16) 0.0006(17) C4A 0.024(2) 0.018(2) 0.018(2) 0.0003(16) 0.0091(17) -0.0010(16) C5A 0.023(2) 0.017(2) 0.020(2) 0.0024(16) 0.0108(17) -0.0001(16) C6A 0.0159(19) 0.025(2) 0.0152(19) 0.0001(17) 0.0050(16) -0.0001(17) C7A 0.0133(18) 0.020(2) 0.020(2) 0.0012(17) 0.0063(16) 0.0010(16) C8A 0.0165(19) 0.021(2) 0.019(2) -0.0023(17) 0.0060(17) 0.0015(16) C9A 0.030(2) 0.020(2) 0.023(2) -0.0037(17) 0.0108(19) -0.0024(18) C1B 0.111(5) 0.026(3) 0.058(4) 0.004(2) 0.058(4) -0.001(3) C2B 0.040(3) 0.025(2) 0.028(2) 0.0003(19) 0.018(2) -0.001(2) C3B 0.029(2) 0.021(2) 0.025(2) -0.0018(18) 0.0121(19) -0.0018(18) C4B 0.023(2) 0.024(2) 0.021(2) -0.0004(17) 0.0080(18) -0.0006(17) C5B 0.026(2) 0.025(2) 0.023(2) 0.0014(18) 0.0079(18) 0.0010(18) C6B 0.0181(19) 0.023(2) 0.022(2) -0.0020(17) 0.0105(17) 0.0005(17) C7B 0.0159(19) 0.022(2) 0.022(2) 0.0012(17) 0.0074(17) 0.0026(17) C8B 0.020(2) 0.022(2) 0.021(2) -0.0005(17) 0.0067(17) 0.0026(17) C9B 0.037(2) 0.026(2) 0.026(2) -0.0033(19) 0.012(2) -0.002(2) Li1A 0.024(3) 0.025(4) 0.021(3) -0.004(3) 0.007(3) -0.007(3) Li1B 0.027(4) 0.034(4) 0.023(4) -0.002(3) 0.011(3) 0.005(3) C1F 0.045(3) 0.086(4) 0.038(3) -0.008(3) 0.012(3) 0.020(3) O1F 0.0223(15) 0.0341(17) 0.0259(16) -0.0070(13) 0.0078(13) 0.0025(13) O1W 0.0246(15) 0.0375(17) 0.0221(15) 0.0041(13) 0.0073(13) -0.0026(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cu1A N3A 1.899(3) . ? Cu1A N2A 1.910(3) . ? Cu1A N4A 1.939(3) . ? Cu1A N1A 1.964(3) . ? Cu1B N3B 1.900(3) . ? Cu1B N2B 1.922(3) . ? Cu1B N4B 1.947(3) . ? Cu1B N1B 1.969(3) . ? Cu1B O5A 2.270(3) . ? O1A N1A 1.384(4) . ? O1A H1A 0.9363 . ? O2A C3A 1.242(5) . ? O2A Li1A 2.146(7) . ? O3A C7A 1.249(5) . ? O3A Li1A 2.040(7) 2_745 ? O4A N4A 1.350(4) . ? O5A C4A 1.422(5) . ? O5A C5A 1.440(4) . ? O1B N1B 1.377(4) . ? O1B H1B 1.0105 . ? O2B C3B 1.258(5) . ? O2B Li1B 2.031(7) . ? O3B C7B 1.242(5) . ? O3B Li1B 2.078(7) 2_645 ? O4B N4B 1.348(4) . ? O5B C4B 1.422(5) . ? O5B C5B 1.426(5) . ? N1A C2A 1.280(5) . ? N2A C3A 1.317(5) . ? N2A N5A 1.449(4) . ? N3A C7A 1.329(5) . ? N3A N6A 1.449(4) . ? N4A C8A 1.296(5) . ? N5A C4A 1.457(5) . ? N5A C6A 1.476(5) . ? N5A Li1A 2.125(7) . ? N6A C5A 1.462(5) . ? N6A C6A 1.485(5) . ? N6A Li1A 2.160(7) 2_745 ? N1B C2B 1.270(5) . ? N2B C3B 1.308(5) . ? N2B N5B 1.447(4) . ? N3B C7B 1.334(5) . ? N3B N6B 1.440(4) . ? N4B C8B 1.287(5) . ? N5B C4B 1.459(5) . ? N5B C6B 1.478(5) . ? N5B Li1B 2.181(8) . ? N6B C5B 1.456(5) . ? N6B C6B 1.473(5) . ? N6B Li1B 2.137(8) 2_645 ? C1A C2A 1.478(5) . ? C1A H1AA 0.9800 . ? C1A H1AB 0.9800 . ? C1A H1AC 0.9800 . ? C2A C3A 1.534(5) . ? C4A H4AB 0.9900 . ? C4A H4AA 0.9900 . ? C5A H5AA 0.9900 . ? C5A H5AB 0.9900 . ? C6A H6AB 0.9900 . ? C6A H6AA 0.9900 . ? C7A C8A 1.522(5) . ? C7A Li1A 2.737(8) 2_745 ? C8A C9A 1.488(5) . ? C9A H9AA 0.9800 . ? C9A H9AB 0.9800 . ? C9A H9AC 0.9800 . ? C1B C2B 1.489(6) . ? C1B H1BB 0.9800 . ? C1B H1BC 0.9800 . ? C1B H1BA 0.9800 . ? C2B C3B 1.533(6) . ? C3B Li1B 2.722(8) . ? C4B H4BB 0.9900 . ? C4B H4BA 0.9900 . ? C5B H5BB 0.9900 . ? C5B H5BA 0.9900 . ? C6B H6BB 0.9900 . ? C6B H6BA 0.9900 . ? C7B C8B 1.524(5) . ? C7B Li1B 2.715(7) 2_645 ? C8B C9B 1.495(6) . ? C9B H9BA 0.9800 . ? C9B H9BB 0.9800 . ? C9B H9BC 0.9800 . ? Li1A O1F 1.922(7) . ? Li1A O3A 2.040(7) 2_755 ? Li1A N6A 2.160(7) 2_755 ? Li1A C7A 2.737(8) 2_755 ? Li1B O1W 1.900(8) . ? Li1B O3B 2.078(7) 2_655 ? Li1B N6B 2.137(8) 2_655 ? Li1B C7B 2.715(7) 2_655 ? C1F O1F 1.414(6) . ? C1F H1FB 0.9500 . ? C1F H1FA 0.9500 . ? O1W H1WB 0.8696 . ? O1W H1WA 1.0033 . ? 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 N3A Cu1A N2A 96.03(13) . . ? N3A Cu1A N4A 82.86(13) . . ? N2A Cu1A N4A 165.48(13) . . ? N3A Cu1A N1A 172.63(13) . . ? N2A Cu1A N1A 80.49(13) . . ? N4A Cu1A N1A 98.87(13) . . ? N3B Cu1B N2B 96.02(13) . . ? N3B Cu1B N4B 82.09(13) . . ? N2B Cu1B N4B 167.80(14) . . ? N3B Cu1B N1B 160.48(14) . . ? N2B Cu1B N1B 80.75(13) . . ? N4B Cu1B N1B 96.97(13) . . ? N3B Cu1B O5A 98.33(12) . . ? N2B Cu1B O5A 101.49(12) . . ? N4B Cu1B O5A 90.71(11) . . ? N1B Cu1B O5A 101.18(12) . . ? N1A O1A H1A 100.8 . . ? C3A O2A Li1A 105.1(3) . . ? C7A O3A Li1A 110.3(3) . 2_745 ? C4A O5A C5A 110.9(3) . . ? C4A O5A Cu1B 125.4(2) . . ? C5A O5A Cu1B 123.6(2) . . ? N1B O1B H1B 104.8 . . ? C3B O2B Li1B 109.5(3) . . ? C7B O3B Li1B 107.0(3) . 2_645 ? C4B O5B C5B 109.5(3) . . ? C2A N1A O1A 118.3(3) . . ? C2A N1A Cu1A 116.9(3) . . ? O1A N1A Cu1A 124.4(2) . . ? C3A N2A N5A 115.1(3) . . ? C3A N2A Cu1A 118.2(2) . . ? N5A N2A Cu1A 126.3(2) . . ? C7A N3A N6A 115.7(3) . . ? C7A N3A Cu1A 115.1(2) . . ? N6A N3A Cu1A 124.7(2) . . ? C8A N4A O4A 121.7(3) . . ? C8A N4A Cu1A 115.3(3) . . ? O4A N4A Cu1A 122.8(2) . . ? N2A N5A C4A 109.1(3) . . ? N2A N5A C6A 109.2(3) . . ? C4A N5A C6A 109.2(3) . . ? N2A N5A Li1A 105.0(3) . . ? C4A N5A Li1A 105.8(3) . . ? C6A N5A Li1A 118.2(3) . . ? N3A N6A C5A 110.8(3) . . ? N3A N6A C6A 109.5(3) . . ? C5A N6A C6A 108.6(3) . . ? N3A N6A Li1A 104.8(3) . 2_745 ? C5A N6A Li1A 101.5(3) . 2_745 ? C6A N6A Li1A 121.2(3) . 2_745 ? C2B N1B O1B 118.8(3) . . ? C2B N1B Cu1B 116.3(3) . . ? O1B N1B Cu1B 124.9(2) . . ? C3B N2B N5B 114.5(3) . . ? C3B N2B Cu1B 115.6(3) . . ? N5B N2B Cu1B 123.8(2) . . ? C7B N3B N6B 115.6(3) . . ? C7B N3B Cu1B 116.6(3) . . ? N6B N3B Cu1B 126.3(2) . . ? C8B N4B O4B 123.2(3) . . ? C8B N4B Cu1B 115.8(3) . . ? O4B N4B Cu1B 121.0(2) . . ? N2B N5B C4B 110.4(3) . . ? N2B N5B C6B 110.6(3) . . ? C4B N5B C6B 108.0(3) . . ? N2B N5B Li1B 104.7(3) . . ? C4B N5B Li1B 105.0(3) . . ? C6B N5B Li1B 118.1(3) . . ? N3B N6B C5B 110.1(3) . . ? N3B N6B C6B 109.4(3) . . ? C5B N6B C6B 108.4(3) . . ? N3B N6B Li1B 104.3(3) . 2_645 ? C5B N6B Li1B 113.6(3) . 2_645 ? C6B N6B Li1B 110.9(3) . 2_645 ? C2A C1A H1AA 109.5 . . ? C2A C1A H1AB 109.5 . . ? H1AA C1A H1AB 109.5 . . ? C2A C1A H1AC 109.5 . . ? H1AA C1A H1AC 109.5 . . ? H1AB C1A H1AC 109.5 . . ? N1A C2A C1A 126.4(3) . . ? N1A C2A C3A 112.2(3) . . ? C1A C2A C3A 121.4(3) . . ? O2A C3A N2A 128.0(4) . . ? O2A C3A C2A 120.7(3) . . ? N2A C3A C2A 111.3(3) . . ? O5A C4A N5A 111.3(3) . . ? O5A C4A H4AB 109.4 . . ? N5A C4A H4AB 109.4 . . ? O5A C4A H4AA 109.4 . . ? N5A C4A H4AA 109.4 . . ? H4AB C4A H4AA 108.0 . . ? O5A C5A N6A 112.8(3) . . ? O5A C5A H5AA 109.0 . . ? N6A C5A H5AA 109.0 . . ? O5A C5A H5AB 109.0 . . ? N6A C5A H5AB 109.0 . . ? H5AA C5A H5AB 107.8 . . ? N5A C6A N6A 115.6(3) . . ? N5A C6A H6AB 108.4 . . ? N6A C6A H6AB 108.4 . . ? N5A C6A H6AA 108.4 . . ? N6A C6A H6AA 108.4 . . ? H6AB C6A H6AA 107.4 . . ? O3A C7A N3A 127.3(4) . . ? O3A C7A C8A 120.6(3) . . ? N3A C7A C8A 112.1(3) . . ? O3A C7A Li1A 44.4(2) . 2_745 ? N3A C7A Li1A 83.0(3) . 2_745 ? C8A C7A Li1A 164.8(3) . 2_745 ? N4A C8A C9A 125.1(4) . . ? N4A C8A C7A 112.8(3) . . ? C9A C8A C7A 122.1(3) . . ? C8A C9A H9AA 109.5 . . ? C8A C9A H9AB 109.5 . . ? H9AA C9A H9AB 109.5 . . ? C8A C9A H9AC 109.5 . . ? H9AA C9A H9AC 109.5 . . ? H9AB C9A H9AC 109.5 . . ? C2B C1B H1BB 109.5 . . ? C2B C1B H1BC 109.5 . . ? H1BB C1B H1BC 109.5 . . ? C2B C1B H1BA 109.5 . . ? H1BB C1B H1BA 109.5 . . ? H1BC C1B H1BA 109.5 . . ? N1B C2B C1B 125.9(4) . . ? N1B C2B C3B 112.5(4) . . ? C1B C2B C3B 121.4(4) . . ? O2B C3B N2B 129.1(4) . . ? O2B C3B C2B 119.0(4) . . ? N2B C3B C2B 111.8(3) . . ? O2B C3B Li1B 44.7(2) . . ? N2B C3B Li1B 84.6(3) . . ? C2B C3B Li1B 163.5(3) . . ? O5B C4B N5B 113.8(3) . . ? O5B C4B H4BB 108.8 . . ? N5B C4B H4BB 108.8 . . ? O5B C4B H4BA 108.8 . . ? N5B C4B H4BA 108.8 . . ? H4BB C4B H4BA 107.7 . . ? O5B C5B N6B 113.1(3) . . ? O5B C5B H5BB 109.0 . . ? N6B C5B H5BB 109.0 . . ? O5B C5B H5BA 109.0 . . ? N6B C5B H5BA 109.0 . . ? H5BB C5B H5BA 107.8 . . ? N6B C6B N5B 115.6(3) . . ? N6B C6B H6BB 108.4 . . ? N5B C6B H6BB 108.4 . . ? N6B C6B H6BA 108.4 . . ? N5B C6B H6BA 108.4 . . ? H6BB C6B H6BA 107.4 . . ? O3B C7B N3B 127.3(3) . . ? O3B C7B C8B 121.5(3) . . ? N3B C7B C8B 111.1(3) . . ? O3B C7B Li1B 47.0(2) . 2_645 ? N3B C7B Li1B 82.1(3) . 2_645 ? C8B C7B Li1B 160.8(3) . 2_645 ? N4B C8B C9B 126.6(4) . . ? N4B C8B C7B 113.7(3) . . ? C9B C8B C7B 119.7(3) . . ? C8B C9B H9BA 109.5 . . ? C8B C9B H9BB 109.5 . . ? H9BA C9B H9BB 109.5 . . ? C8B C9B H9BC 109.5 . . ? H9BA C9B H9BC 109.5 . . ? H9BB C9B H9BC 109.5 . . ? O1F Li1A O3A 103.4(3) . 2_755 ? O1F Li1A N5A 112.4(3) . . ? O3A Li1A N5A 93.7(3) 2_755 . ? O1F Li1A O2A 95.2(3) . . ? O3A Li1A O2A 161.4(4) 2_755 . ? N5A Li1A O2A 79.0(3) . . ? O1F Li1A N6A 109.0(3) . 2_755 ? O3A Li1A N6A 81.2(3) 2_755 2_755 ? N5A Li1A N6A 138.4(3) . 2_755 ? O2A Li1A N6A 92.7(3) . 2_755 ? O1F Li1A C7A 108.3(3) . 2_755 ? O3A Li1A C7A 25.34(14) 2_755 2_755 ? N5A Li1A C7A 113.1(3) . 2_755 ? O2A Li1A C7A 145.2(3) . 2_755 ? N6A Li1A C7A 55.93(18) 2_755 2_755 ? O1W Li1B O2B 101.8(3) . . ? O1W Li1B O3B 98.4(3) . 2_655 ? O2B Li1B O3B 159.7(4) . 2_655 ? O1W Li1B N6B 103.3(3) . 2_655 ? O2B Li1B N6B 94.5(3) . 2_655 ? O3B Li1B N6B 80.7(3) 2_655 2_655 ? O1W Li1B N5B 112.7(4) . . ? O2B Li1B N5B 80.5(3) . . ? O3B Li1B N5B 91.8(3) 2_655 . ? N6B Li1B N5B 143.9(4) 2_655 . ? O1W Li1B C7B 94.6(3) . 2_655 ? O2B Li1B C7B 149.4(4) . 2_655 ? O3B Li1B C7B 25.93(14) 2_655 2_655 ? N6B Li1B C7B 56.39(19) 2_655 2_655 ? N5B Li1B C7B 116.6(3) . 2_655 ? O1W Li1B C3B 105.9(3) . . ? O2B Li1B C3B 25.84(14) . . ? O3B Li1B C3B 144.5(4) 2_655 . ? N6B Li1B C3B 117.3(3) 2_655 . ? N5B Li1B C3B 55.11(19) . . ? C7B Li1B C3B 159.6(3) 2_655 . ? O1F C1F H1FB 120.0 . . ? O1F C1F H1FA 120.0 . . ? H1FB C1F H1FA 120.0 . . ? C1F O1F Li1A 128.5(3) . . ? Li1B O1W H1WB 111.2 . . ? Li1B O1W H1WA 128.1 . . ? H1WB O1W H1WA 104.0 . . ? 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 O1A H1A O4A 0.94 1.75 2.677(4) 169.6 . O1B H1B O4B 1.01 1.64 2.623(4) 161.6 . O1W H1WB O4B 0.87 1.82 2.670(4) 166.1 4_566 O1W H1WA O4A 1.00 1.91 2.850(4) 154.8 4_566 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.67 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.688 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.092 # Attachment 'data_3b.cif' data_3b _database_code_depnum_ccdc_archive 'CCDC 610648' _audit_creation_method SHELXL-97 _chemical_name_systematic ; {N,N'-bis(2-Hydroxyiminopropionyl) propane-1,3-diamine)(methylsulfoxide)-cuprate(III)} ; _chemical_name_common ; (N,N'-bis(2-Hydroxyiminopropionyl) propane-1,3- diamine)(methylsulfoxide)-cuprate(iii)) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H19 Cu N6 O6 S' _chemical_formula_weight 426.92 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.144(2) _cell_length_b 9.362(2) _cell_length_c 11.394(2) _cell_angle_alpha 91.83(3) _cell_angle_beta 91.08(3) _cell_angle_gamma 111.53(3) _cell_volume 807.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.756 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 1.527 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6554 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 28.43 _reflns_number_total 3596 _reflns_number_gt 3088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3596 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0843 _refine_ls_wR_factor_gt 0.0822 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.67808(3) 0.66935(3) 0.67714(2) 0.01097(9) Uani 1 1 d . . . S1 S 0.67798(7) 0.77673(6) 0.95984(4) 0.01464(13) Uani 1 1 d . . . O1 O 0.4857(2) 0.34820(16) 0.68995(14) 0.0164(3) Uani 1 1 d . . . O2 O 0.2333(2) 0.69122(18) 0.55693(14) 0.0199(3) Uani 1 1 d . . . O3 O 1.1424(2) 0.96115(18) 0.78537(15) 0.0231(4) Uani 1 1 d . . . O4 O 0.7958(2) 0.44014(17) 0.76821(14) 0.0187(3) Uani 1 1 d . . . O5 O 0.64073(19) 0.99577(17) 0.77674(13) 0.0158(3) Uani 1 1 d . . . O6 O 0.5712(2) 0.66189(17) 0.86484(12) 0.0172(3) Uani 1 1 d . . . N1 N 0.4808(2) 0.48157(19) 0.65310(14) 0.0121(4) Uani 1 1 d . . . N2 N 0.5330(2) 0.74908(19) 0.58939(15) 0.0127(4) Uani 1 1 d . . . N3 N 0.8794(2) 0.85259(19) 0.67754(16) 0.0138(4) Uani 1 1 d . . . N4 N 0.8431(2) 0.5885(2) 0.74398(15) 0.0139(4) Uani 1 1 d . . . N5 N 0.5732(2) 0.90357(19) 0.57614(15) 0.0130(4) Uani 1 1 d . . . N6 N 0.8726(2) 0.99439(19) 0.65108(16) 0.0152(4) Uani 1 1 d . . . C1 C 0.1588(3) 0.3713(2) 0.6051(2) 0.0189(5) Uani 1 1 d . . . H1A H 0.1629 0.2798 0.6385 0.028 Uiso 1 1 calc R . . H1B H 0.1219 0.3504 0.5238 0.028 Uiso 1 1 calc R . . H1C H 0.0763 0.4041 0.6465 0.028 Uiso 1 1 calc R . . C2 C 0.3355(3) 0.4936(2) 0.61512(18) 0.0129(4) Uani 1 1 d . . . C3 C 0.3593(3) 0.6554(2) 0.58454(18) 0.0131(4) Uani 1 1 d . . . C4 C 0.5281(3) 0.9850(2) 0.67472(18) 0.0153(4) Uani 1 1 d . . . H4A H 0.5409 1.0875 0.6522 0.018 Uiso 1 1 calc R . . H4B H 0.4059 0.9310 0.6940 0.018 Uiso 1 1 calc R . . C5 C 0.8215(3) 1.0723(2) 0.7486(2) 0.0180(5) Uani 1 1 d . . . H5A H 0.8961 1.0771 0.8171 0.022 Uiso 1 1 calc R . . H5B H 0.8404 1.1768 0.7281 0.022 Uiso 1 1 calc R . . C6 C 0.7579(3) 0.9816(2) 0.54611(18) 0.0154(4) Uani 1 1 d . . . H6A H 0.7756 1.0833 0.5190 0.018 Uiso 1 1 calc R . . H6B H 0.7878 0.9239 0.4834 0.018 Uiso 1 1 calc R . . C7 C 1.0146(3) 0.8499(2) 0.74897(19) 0.0156(4) Uani 1 1 d . . . C8 C 0.9924(3) 0.6892(2) 0.78021(19) 0.0146(4) Uani 1 1 d . . . C9 C 1.1288(3) 0.6572(3) 0.8520(2) 0.0237(5) Uani 1 1 d . . . H9A H 1.0890 0.5493 0.8657 0.035 Uiso 1 1 calc R . . H9B H 1.1480 0.7141 0.9259 0.035 Uiso 1 1 calc R . . H9C H 1.2372 0.6875 0.8108 0.035 Uiso 1 1 calc R . . C10 C 0.5196(3) 0.8139(3) 1.0483(2) 0.0211(5) Uani 1 1 d . . . H10A H 0.4592 0.8658 1.0035 0.032 Uiso 1 1 calc R . . H10B H 0.5783 0.8775 1.1158 0.032 Uiso 1 1 calc R . . H10C H 0.4359 0.7186 1.0736 0.032 Uiso 1 1 calc R . . C11 C 0.7505(3) 0.6702(3) 1.0637(2) 0.0225(5) Uani 1 1 d . . . H11A H 0.6509 0.5839 1.0870 0.034 Uiso 1 1 calc R . . H11B H 0.8043 0.7354 1.1314 0.034 Uiso 1 1 calc R . . H11C H 0.8349 0.6343 1.0281 0.034 Uiso 1 1 calc R . . H1O1 H 0.612(6) 0.376(5) 0.724(4) 0.085(13) 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 Cu1 0.01148(14) 0.00872(14) 0.01340(14) 0.00127(9) 0.00050(9) 0.00444(10) S1 0.0150(3) 0.0145(3) 0.0131(3) 0.00093(19) 0.0005(2) 0.0038(2) O1 0.0215(8) 0.0089(7) 0.0194(8) 0.0019(6) -0.0008(6) 0.0065(6) O2 0.0158(8) 0.0192(8) 0.0257(9) 0.0040(6) -0.0023(7) 0.0077(6) O3 0.0136(8) 0.0197(8) 0.0331(10) -0.0012(7) -0.0020(7) 0.0032(6) O4 0.0224(8) 0.0121(7) 0.0254(9) 0.0056(6) 0.0016(7) 0.0102(7) O5 0.0136(7) 0.0156(7) 0.0178(8) -0.0004(6) 0.0002(6) 0.0048(6) O6 0.0192(8) 0.0170(8) 0.0116(7) -0.0012(6) 0.0013(6) 0.0022(6) N1 0.0166(9) 0.0091(8) 0.0116(8) 0.0002(6) 0.0023(7) 0.0059(7) N2 0.0143(9) 0.0102(8) 0.0141(9) 0.0020(7) -0.0020(7) 0.0051(7) N3 0.0125(8) 0.0093(8) 0.0203(9) 0.0030(7) 0.0015(7) 0.0045(7) N4 0.0156(9) 0.0134(9) 0.0157(9) 0.0025(7) 0.0039(7) 0.0085(7) N5 0.0141(9) 0.0107(8) 0.0165(9) 0.0032(7) 0.0009(7) 0.0069(7) N6 0.0141(9) 0.0094(9) 0.0221(10) 0.0013(7) 0.0030(7) 0.0043(7) C1 0.0176(11) 0.0152(11) 0.0211(11) -0.0017(9) 0.0003(9) 0.0030(9) C2 0.0132(10) 0.0158(10) 0.0094(9) 0.0014(8) 0.0022(8) 0.0047(8) C3 0.0145(10) 0.0132(10) 0.0113(9) 0.0002(8) 0.0001(8) 0.0046(8) C4 0.0155(10) 0.0133(10) 0.0188(11) -0.0007(8) -0.0004(8) 0.0075(8) C5 0.0147(10) 0.0138(10) 0.0250(12) -0.0014(9) 0.0023(9) 0.0048(8) C6 0.0159(10) 0.0135(10) 0.0169(10) 0.0063(8) 0.0053(8) 0.0051(8) C7 0.0134(10) 0.0170(11) 0.0181(11) -0.0002(8) 0.0042(8) 0.0073(9) C8 0.0132(10) 0.0173(10) 0.0159(10) 0.0013(8) 0.0016(8) 0.0085(8) C9 0.0191(11) 0.0267(13) 0.0282(13) 0.0055(10) -0.0018(10) 0.0117(10) C10 0.0228(12) 0.0231(12) 0.0194(11) -0.0064(9) -0.0015(9) 0.0116(10) C11 0.0188(11) 0.0268(13) 0.0246(12) 0.0072(10) 0.0018(9) 0.0108(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N3 1.8882(19) . ? Cu1 N2 1.8985(18) . ? Cu1 N1 1.9042(19) . ? Cu1 N4 1.9241(18) . ? Cu1 O6 2.3178(16) . ? S1 O6 1.5126(16) . ? S1 C10 1.777(2) . ? S1 C11 1.796(2) . ? O1 N1 1.344(2) . ? O1 H1O1 1.03(4) . ? O2 C3 1.229(3) . ? O3 C7 1.225(3) . ? O4 N4 1.338(2) . ? O4 H1O1 1.46(5) . ? O5 C5 1.429(3) . ? O5 C4 1.445(2) . ? N1 C2 1.297(3) . ? N2 C3 1.362(3) . ? N2 N5 1.375(2) . ? N3 C7 1.365(3) . ? N3 N6 1.391(2) . ? N4 C8 1.286(3) . ? N5 C6 1.463(3) . ? N5 C4 1.464(3) . ? N6 C5 1.459(3) . ? N6 C6 1.478(3) . ? C1 C2 1.473(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.508(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.503(3) . ? C8 C9 1.490(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 N3 Cu1 N2 94.49(8) . . ? N3 Cu1 N1 171.68(7) . . ? N2 Cu1 N1 82.82(8) . . ? N3 Cu1 N4 82.85(8) . . ? N2 Cu1 N4 171.26(7) . . ? N1 Cu1 N4 98.63(8) . . ? N3 Cu1 O6 104.96(7) . . ? N2 Cu1 O6 102.80(7) . . ? N1 Cu1 O6 83.33(7) . . ? N4 Cu1 O6 85.94(7) . . ? O6 S1 C10 105.20(10) . . ? O6 S1 C11 106.46(11) . . ? C10 S1 C11 97.69(11) . . ? N1 O1 H1O1 105(2) . . ? N4 O4 H1O1 102.2(16) . . ? C5 O5 C4 109.86(16) . . ? S1 O6 Cu1 120.13(9) . . ? C2 N1 O1 121.95(18) . . ? C2 N1 Cu1 115.99(14) . . ? O1 N1 Cu1 121.34(13) . . ? C3 N2 N5 117.80(17) . . ? C3 N2 Cu1 113.34(13) . . ? N5 N2 Cu1 123.30(14) . . ? C7 N3 N6 118.46(17) . . ? C7 N3 Cu1 113.24(14) . . ? N6 N3 Cu1 123.44(13) . . ? C8 N4 O4 121.70(18) . . ? C8 N4 Cu1 115.55(15) . . ? O4 N4 Cu1 121.92(14) . . ? N2 N5 C6 111.64(16) . . ? N2 N5 C4 115.28(17) . . ? C6 N5 C4 110.60(17) . . ? N3 N6 C5 114.23(17) . . ? N3 N6 C6 111.38(16) . . ? C5 N6 C6 110.44(17) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C1 127.2(2) . . ? N1 C2 C3 112.78(18) . . ? C1 C2 C3 119.93(18) . . ? O2 C3 N2 126.69(19) . . ? O2 C3 C2 121.84(19) . . ? N2 C3 C2 111.46(17) . . ? O5 C4 N5 111.03(16) . . ? O5 C4 H4A 109.4 . . ? N5 C4 H4A 109.4 . . ? O5 C4 H4B 109.4 . . ? N5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? O5 C5 N6 112.04(17) . . ? O5 C5 H5A 109.2 . . ? N6 C5 H5A 109.2 . . ? O5 C5 H5B 109.2 . . ? N6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N5 C6 N6 109.21(17) . . ? N5 C6 H6A 109.8 . . ? N6 C6 H6A 109.8 . . ? N5 C6 H6B 109.8 . . ? N6 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? O3 C7 N3 126.5(2) . . ? O3 C7 C8 121.5(2) . . ? N3 C7 C8 112.05(18) . . ? N4 C8 C9 125.3(2) . . ? N4 C8 C7 112.99(19) . . ? C9 C8 C7 121.60(19) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? S1 C10 H10A 109.5 . . ? S1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? S1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? S1 C11 H11A 109.5 . . ? S1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? S1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 C10 S1 O6 Cu1 145.66(11) . . . . ? C11 S1 O6 Cu1 -111.35(11) . . . . ? N3 Cu1 O6 S1 -8.82(12) . . . . ? N2 Cu1 O6 S1 -107.09(11) . . . . ? N1 Cu1 O6 S1 171.86(11) . . . . ? N4 Cu1 O6 S1 72.67(11) . . . . ? N3 Cu1 N1 C2 -85.1(5) . . . . ? N2 Cu1 N1 C2 -13.47(15) . . . . ? N4 Cu1 N1 C2 175.23(15) . . . . ? O6 Cu1 N1 C2 90.39(15) . . . . ? N3 Cu1 N1 O1 104.5(5) . . . . ? N2 Cu1 N1 O1 176.07(15) . . . . ? N4 Cu1 N1 O1 4.77(16) . . . . ? O6 Cu1 N1 O1 -80.07(14) . . . . ? N3 Cu1 N2 C3 -170.21(14) . . . . ? N1 Cu1 N2 C3 17.71(14) . . . . ? N4 Cu1 N2 C3 117.9(5) . . . . ? O6 Cu1 N2 C3 -63.74(15) . . . . ? N3 Cu1 N2 N5 -17.21(17) . . . . ? N1 Cu1 N2 N5 170.71(17) . . . . ? N4 Cu1 N2 N5 -89.1(5) . . . . ? O6 Cu1 N2 N5 89.26(16) . . . . ? N2 Cu1 N3 C7 171.52(14) . . . . ? N1 Cu1 N3 C7 -117.7(5) . . . . ? N4 Cu1 N3 C7 -16.85(14) . . . . ? O6 Cu1 N3 C7 66.98(15) . . . . ? N2 Cu1 N3 N6 16.70(17) . . . . ? N1 Cu1 N3 N6 87.5(5) . . . . ? N4 Cu1 N3 N6 -171.67(17) . . . . ? O6 Cu1 N3 N6 -87.84(16) . . . . ? N3 Cu1 N4 C8 13.38(16) . . . . ? N2 Cu1 N4 C8 86.2(5) . . . . ? N1 Cu1 N4 C8 -174.88(15) . . . . ? O6 Cu1 N4 C8 -92.27(16) . . . . ? N3 Cu1 N4 O4 -176.85(16) . . . . ? N2 Cu1 N4 O4 -104.1(5) . . . . ? N1 Cu1 N4 O4 -5.11(16) . . . . ? O6 Cu1 N4 O4 77.50(15) . . . . ? C3 N2 N5 C6 -161.94(17) . . . . ? Cu1 N2 N5 C6 46.2(2) . . . . ? C3 N2 N5 C4 70.8(2) . . . . ? Cu1 N2 N5 C4 -81.1(2) . . . . ? C7 N3 N6 C5 -72.4(2) . . . . ? Cu1 N3 N6 C5 81.2(2) . . . . ? C7 N3 N6 C6 161.64(17) . . . . ? Cu1 N3 N6 C6 -44.8(2) . . . . ? O1 N1 C2 C1 -0.2(3) . . . . ? Cu1 N1 C2 C1 -170.61(16) . . . . ? O1 N1 C2 C3 176.96(16) . . . . ? Cu1 N1 C2 C3 6.6(2) . . . . ? N5 N2 C3 O2 8.4(3) . . . . ? Cu1 N2 C3 O2 163.01(18) . . . . ? N5 N2 C3 C2 -173.05(16) . . . . ? Cu1 N2 C3 C2 -18.5(2) . . . . ? N1 C2 C3 O2 -173.54(19) . . . . ? C1 C2 C3 O2 3.9(3) . . . . ? N1 C2 C3 N2 7.8(2) . . . . ? C1 C2 C3 N2 -174.75(17) . . . . ? C5 O5 C4 N5 57.9(2) . . . . ? N2 N5 C4 O5 69.4(2) . . . . ? C6 N5 C4 O5 -58.4(2) . . . . ? C4 O5 C5 N6 -57.7(2) . . . . ? N3 N6 C5 O5 -69.1(2) . . . . ? C6 N6 C5 O5 57.3(2) . . . . ? N2 N5 C6 N6 -73.1(2) . . . . ? C4 N5 C6 N6 56.7(2) . . . . ? N3 N6 C6 N5 72.2(2) . . . . ? C5 N6 C6 N5 -55.8(2) . . . . ? N6 N3 C7 O3 -6.9(3) . . . . ? Cu1 N3 C7 O3 -163.06(18) . . . . ? N6 N3 C7 C8 173.53(17) . . . . ? Cu1 N3 C7 C8 17.4(2) . . . . ? O4 N4 C8 C9 -0.3(3) . . . . ? Cu1 N4 C8 C9 169.48(17) . . . . ? O4 N4 C8 C7 -176.81(16) . . . . ? Cu1 N4 C8 C7 -7.0(2) . . . . ? O3 C7 C8 N4 173.67(19) . . . . ? N3 C7 C8 N4 -6.7(3) . . . . ? O3 C7 C8 C9 -3.0(3) . . . . ? N3 C7 C8 C9 176.63(18) . . . . ? 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 O1 H1O1 O4 1.03(4) 1.46(4) 2.487(2) 171(4) . _diffrn_measured_fraction_theta_max 0.885 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.885 _refine_diff_density_max 0.567 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.091 # Attachment 'data_5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 610649' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(dicopper(II)(N,N'-bis(2-oxyiminopropionyl) propane-1,3-diamine)(2,2'-dipyridine) pentahydrate ; _chemical_name_common ; bis(dicopper(ii)(N,N'-bis(2-oxyiminopropionyl) propane-1,3- diamine)(2,2'-dipyridine) pentahydrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H30 Cu2 N8 O10' _chemical_formula_weight 657.59 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.8590(13) _cell_length_b 7.0434(8) _cell_length_c 27.665(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.603(2) _cell_angle_gamma 90.00 _cell_volume 2500.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 1.772 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11475 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 7.30 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5490 _reflns_number_gt 4053 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0912P)^2^+0.0757P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5490 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1488 _refine_ls_wR_factor_gt 0.1397 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.18051(3) 0.13857(7) 0.405022(15) 0.03638(16) Uani 1 1 d . . . Cu2 Cu 0.02621(3) 0.23386(7) 0.510584(14) 0.03424(16) Uani 1 1 d . . . O1 O 0.1737(2) 0.2255(4) 0.51084(9) 0.0424(6) Uani 1 1 d . . . O2 O 0.4812(2) 0.2444(7) 0.43419(12) 0.0746(12) Uani 1 1 d . . . O3 O -0.0031(2) 0.0470(5) 0.28583(9) 0.0480(7) Uani 1 1 d . . . O4 O -0.02252(18) 0.1073(4) 0.45209(8) 0.0370(6) Uani 1 1 d . . . O5 O 0.2685(2) 0.3912(5) 0.31355(12) 0.0588(8) Uani 1 1 d . . . N1 N 0.2294(2) 0.2058(5) 0.47144(11) 0.0373(7) Uani 1 1 d . . . N2 N 0.3258(2) 0.1511(6) 0.39524(12) 0.0467(9) Uani 1 1 d . . . N3 N 0.1420(2) 0.0731(5) 0.33889(11) 0.0433(8) Uani 1 1 d . . . N4 N 0.0299(2) 0.1074(4) 0.41094(10) 0.0325(6) Uani 1 1 d . . . N5 N 0.3723(3) 0.1449(6) 0.34929(13) 0.0505(9) Uani 1 1 d . . . N6 N 0.2097(2) 0.0739(6) 0.29956(11) 0.0449(8) Uani 1 1 d . . . N7 N -0.1252(2) 0.2727(4) 0.52460(11) 0.0358(7) Uani 1 1 d . . . N8 N 0.0439(2) 0.3684(4) 0.57573(10) 0.0350(7) Uani 1 1 d . . . C1 C 0.3860(4) 0.2423(8) 0.52604(17) 0.0577(12) Uani 1 1 d . . . H2A H 0.3370 0.2471 0.5508 0.080 Uiso 1 1 d R . . H2B H 0.4333 0.1385 0.5324 0.080 Uiso 1 1 d R . . H2C H 0.4245 0.3592 0.5260 0.080 Uiso 1 1 d R . . C2 C 0.3294(3) 0.2154(6) 0.47824(14) 0.0426(9) Uani 1 1 d . . . C3 C 0.3881(3) 0.2033(7) 0.43291(15) 0.0467(10) Uani 1 1 d . . . C7 C 0.0406(3) 0.0620(6) 0.32702(12) 0.0356(8) Uani 1 1 d . . . C8 C -0.0236(3) 0.0691(5) 0.37119(12) 0.0325(7) Uani 1 1 d . . . C9 C -0.1374(3) 0.0374(6) 0.36680(13) 0.0392(8) Uani 1 1 d . . . H9A H -0.1644 0.0464 0.3983 0.080 Uiso 1 1 d R . . H9B H -0.1695 0.1324 0.3459 0.080 Uiso 1 1 d R . . H9C H -0.1523 -0.0862 0.3535 0.080 Uiso 1 1 d R . . C6 C 0.3160(3) 0.0081(7) 0.31801(15) 0.0532(11) Uani 1 1 d . . . H6A H 0.3090 -0.1081 0.3356 0.080 Uiso 1 1 d R . . H6B H 0.3565 -0.0182 0.2908 0.080 Uiso 1 1 d R . . C4 C 0.3715(3) 0.3260(8) 0.32677(17) 0.0569(12) Uani 1 1 d . . . H4A H 0.4055 0.4163 0.3484 0.080 Uiso 1 1 d R . . H4B H 0.4103 0.3187 0.2983 0.080 Uiso 1 1 d R . . C5 C 0.2184(4) 0.2605(7) 0.27966(15) 0.0517(11) Uani 1 1 d . . . H5A H 0.2584 0.2527 0.2516 0.080 Uiso 1 1 d R . . H5B H 0.1503 0.3072 0.2696 0.080 Uiso 1 1 d R . . C10 C -0.2085(3) 0.2390(6) 0.49416(15) 0.0437(9) Uani 1 1 d . . . H10A H -0.1972 0.1955 0.4620 0.080 Uiso 1 1 d R . . C11 C -0.3093(3) 0.2627(6) 0.50774(17) 0.0486(10) Uani 1 1 d . . . H11A H -0.3677 0.2400 0.4851 0.080 Uiso 1 1 d R . . C12 C -0.3247(3) 0.3199(7) 0.55412(17) 0.0506(10) Uani 1 1 d . . . H12A H -0.3939 0.3331 0.5648 0.080 Uiso 1 1 d R . . C13 C -0.2394(3) 0.3571(6) 0.58551(16) 0.0476(10) Uani 1 1 d . . . H13A H -0.2484 0.3993 0.6180 0.080 Uiso 1 1 d R . . C14 C -0.1409(3) 0.3337(5) 0.57001(13) 0.0344(8) Uani 1 1 d . . . C15 C -0.0448(3) 0.3749(5) 0.59994(13) 0.0341(8) Uani 1 1 d . . . C16 C -0.0428(3) 0.4181(6) 0.64899(13) 0.0410(9) Uani 1 1 d . . . H16A H -0.1061 0.4167 0.6656 0.080 Uiso 1 1 d R . . C17 C 0.0511(3) 0.4614(6) 0.67340(14) 0.0452(9) Uani 1 1 d . . . H17A H 0.0542 0.4897 0.7074 0.080 Uiso 1 1 d R . . C18 C 0.1407(3) 0.4642(6) 0.64804(14) 0.0458(9) Uani 1 1 d . . . H18A H 0.2064 0.4980 0.6641 0.080 Uiso 1 1 d R . . C19 C 0.1335(3) 0.4157(6) 0.59967(14) 0.0409(9) Uani 1 1 d . . . H19A H 0.1956 0.4183 0.5822 0.080 Uiso 1 1 d R . . O1W O -0.1846(3) 0.2219(6) 0.25197(15) 0.0737(10) Uani 1 1 d . . . O2W O -0.3835(4) 0.1358(11) 0.2770(2) 0.135(2) Uani 1 1 d . . . O3W O 0.6204(10) 0.331(10) 0.3647(6) 0.106(11) Uani 0.67(11) 1 d P . . O3WA O 0.612(2) 0.438(13) 0.3650(13) 0.093(12) Uani 0.33(11) 1 d P . . O4W O 0.558(4) 0.622(10) 0.293(2) 0.33(5) Uani 0.32(5) 1 d P . . O4WA O 0.5438(11) 0.683(3) 0.2952(5) 0.151(7) Uani 0.68(5) 1 d P . . O5W O -0.4096(7) -0.0408(18) 0.3565(4) 0.223(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0314(2) 0.0467(3) 0.0312(2) -0.00204(19) 0.00315(16) -0.00293(19) Cu2 0.0315(2) 0.0437(3) 0.0274(2) -0.00246(19) 0.00111(15) -0.00334(18) O1 0.0322(13) 0.0654(19) 0.0297(12) -0.0075(12) 0.0029(10) -0.0050(12) O2 0.0299(15) 0.143(4) 0.0516(18) -0.005(2) 0.0038(13) -0.0112(18) O3 0.0455(15) 0.071(2) 0.0274(12) -0.0005(13) -0.0003(10) 0.0064(14) O4 0.0317(12) 0.0526(16) 0.0272(11) -0.0034(11) 0.0067(9) -0.0060(11) O5 0.0539(18) 0.069(2) 0.0545(18) 0.0019(17) 0.0106(14) -0.0023(15) N1 0.0316(15) 0.0444(18) 0.0362(16) -0.0004(14) 0.0052(12) -0.0021(13) N2 0.0331(16) 0.071(3) 0.0372(17) -0.0096(16) 0.0069(13) 0.0005(16) N3 0.0373(16) 0.060(2) 0.0330(15) -0.0052(15) 0.0061(12) -0.0072(15) N4 0.0340(14) 0.0402(18) 0.0235(13) 0.0012(12) 0.0024(11) -0.0008(12) N5 0.0350(16) 0.072(3) 0.0456(19) -0.0076(19) 0.0103(14) -0.0007(17) N6 0.0402(17) 0.062(2) 0.0332(15) -0.0059(16) 0.0071(13) -0.0005(16) N7 0.0367(16) 0.0384(18) 0.0318(15) 0.0005(13) -0.0015(12) 0.0016(13) N8 0.0381(16) 0.0377(17) 0.0290(14) -0.0006(13) 0.0013(11) -0.0060(13) C1 0.036(2) 0.087(4) 0.049(2) -0.005(2) -0.0047(17) -0.001(2) C2 0.0340(19) 0.054(2) 0.040(2) -0.0022(18) 0.0017(15) -0.0013(17) C3 0.031(2) 0.065(3) 0.044(2) -0.001(2) 0.0041(15) 0.0033(18) C7 0.0419(19) 0.039(2) 0.0263(16) 0.0007(15) 0.0035(13) -0.0003(16) C8 0.0377(18) 0.0325(19) 0.0271(16) 0.0027(14) 0.0005(13) 0.0038(15) C9 0.0341(18) 0.049(2) 0.0337(17) -0.0014(17) -0.0041(14) -0.0034(16) C6 0.045(2) 0.071(3) 0.044(2) -0.011(2) 0.0070(17) 0.008(2) C4 0.039(2) 0.081(4) 0.052(2) -0.004(2) 0.0144(18) -0.005(2) C5 0.053(2) 0.065(3) 0.038(2) -0.001(2) 0.0100(17) 0.001(2) C10 0.041(2) 0.049(2) 0.040(2) -0.0024(18) -0.0055(16) 0.0032(17) C11 0.037(2) 0.054(3) 0.054(2) -0.007(2) -0.0079(17) 0.0020(18) C12 0.038(2) 0.055(3) 0.060(3) -0.009(2) 0.0050(18) 0.0040(18) C13 0.043(2) 0.050(3) 0.050(2) -0.009(2) 0.0052(17) 0.0000(18) C14 0.0382(19) 0.031(2) 0.0341(17) 0.0011(15) 0.0048(14) 0.0016(15) C15 0.0385(18) 0.0308(19) 0.0333(17) -0.0004(15) 0.0042(14) 0.0007(14) C16 0.048(2) 0.041(2) 0.0349(18) -0.0006(17) 0.0064(15) -0.0002(17) C17 0.055(2) 0.048(2) 0.0322(18) -0.0036(18) 0.0007(16) -0.0035(19) C18 0.047(2) 0.048(2) 0.042(2) -0.0074(19) -0.0037(16) -0.0097(18) C19 0.0373(19) 0.046(2) 0.0397(19) -0.0046(18) 0.0018(15) -0.0080(17) O1W 0.059(2) 0.078(3) 0.081(3) 0.018(2) -0.0151(18) -0.0034(18) O2W 0.094(4) 0.208(7) 0.109(4) 0.009(4) 0.046(3) 0.033(4) O3W 0.058(5) 0.14(3) 0.122(7) -0.003(9) 0.034(4) -0.001(8) O3WA 0.066(9) 0.09(3) 0.131(14) 0.009(14) 0.022(8) 0.003(12) O4W 0.30(6) 0.39(7) 0.34(7) 0.25(7) 0.25(6) 0.26(7) O4WA 0.091(8) 0.236(16) 0.129(10) -0.049(10) 0.026(6) -0.068(9) O5W 0.156(7) 0.226(10) 0.292(12) 0.024(9) 0.040(7) 0.059(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N2 1.907(3) . ? Cu1 N3 1.921(3) . ? Cu1 N1 1.962(3) . ? Cu1 N4 1.966(3) . ? Cu1 Cu2 3.6937(6) . ? Cu1 Cu1 7.4862(9) 3_556 ? Cu2 O1 1.897(3) . ? Cu2 O4 1.918(2) . ? Cu2 N7 2.028(3) . ? Cu2 N8 2.036(3) . ? Cu2 O4 2.617(3) 3_556 ? Cu2 Cu2 3.4059(10) 3_556 ? Cu2 O1 4.151(3) 3_556 ? Cu2 Cu1 4.4920(7) 3_556 ? O1 N1 1.349(4) . ? O1 O4 3.030(3) . ? O2 C3 1.231(5) . ? O3 C7 1.243(4) . ? O4 N4 1.359(3) . ? O5 C4 1.428(6) . ? O5 C5 1.437(6) . ? N1 C2 1.291(5) . ? N2 C3 1.325(5) . ? N2 N5 1.439(4) . ? N3 C7 1.327(5) . ? N3 N6 1.436(4) . ? N4 C8 1.288(4) . ? N5 C4 1.419(7) . ? N5 C6 1.457(6) . ? N6 C5 1.432(6) . ? N6 C6 1.501(5) . ? N7 C10 1.341(5) . ? N7 C14 1.355(5) . ? N8 C19 1.334(5) . ? N8 C15 1.360(5) . ? C1 C2 1.481(6) . ? C1 H2A 0.9599 . ? C1 H2B 0.9600 . ? C1 H2C 0.9600 . ? C2 C3 1.506(6) . ? C7 C8 1.518(5) . ? C8 C9 1.478(5) . ? C9 H9A 0.9599 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9599 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C5 H5A 0.9601 . ? C5 H5B 0.9600 . ? C10 C11 1.383(6) . ? C10 H10A 0.9600 . ? C11 C12 1.371(6) . ? C11 H11A 0.9601 . ? C12 C13 1.381(6) . ? C12 H12A 0.9600 . ? C13 C14 1.372(6) . ? C13 H13A 0.9600 . ? C14 C15 1.473(5) . ? C15 C16 1.389(5) . ? C16 C17 1.379(6) . ? C16 H16A 0.9600 . ? C17 C18 1.386(6) . ? C17 H17A 0.9601 . ? C18 C19 1.378(5) . ? C18 H18A 0.9600 . ? C19 H19A 0.9601 . ? O3W O3WA 0.76(3) . ? 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 Cu1 N3 94.16(13) . . ? N2 Cu1 N1 82.11(13) . . ? N3 Cu1 N1 176.27(13) . . ? N2 Cu1 N4 174.97(14) . . ? N3 Cu1 N4 81.72(12) . . ? N1 Cu1 N4 102.01(12) . . ? N2 Cu1 Cu2 133.12(10) . . ? N3 Cu1 Cu2 132.63(9) . . ? N1 Cu1 Cu2 51.10(9) . . ? N4 Cu1 Cu2 51.22(8) . . ? N2 Cu1 Cu1 140.18(11) . 3_556 ? N3 Cu1 Cu1 118.14(9) . 3_556 ? N1 Cu1 Cu1 65.27(9) . 3_556 ? N4 Cu1 Cu1 41.83(8) . 3_556 ? Cu2 Cu1 Cu1 26.465(8) . 3_556 ? O1 Cu2 O4 105.21(10) . . ? O1 Cu2 N7 167.24(12) . . ? O4 Cu2 N7 87.55(11) . . ? O1 Cu2 N8 87.42(11) . . ? O4 Cu2 N8 167.29(11) . . ? N7 Cu2 N8 79.82(12) . . ? O1 Cu2 O4 90.74(11) . 3_556 ? O4 Cu2 O4 83.86(10) . 3_556 ? N7 Cu2 O4 90.40(10) . 3_556 ? N8 Cu2 O4 94.71(10) . 3_556 ? O1 Cu2 Cu2 99.07(9) . 3_556 ? O4 Cu2 Cu2 49.82(8) . 3_556 ? N7 Cu2 Cu2 88.93(9) . 3_556 ? N8 Cu2 Cu2 127.76(9) . 3_556 ? O4 Cu2 Cu2 34.04(5) 3_556 3_556 ? O1 Cu2 Cu1 53.90(8) . . ? O4 Cu2 Cu1 53.97(7) . . ? N7 Cu2 Cu1 138.22(9) . . ? N8 Cu2 Cu1 138.47(8) . . ? O4 Cu2 Cu1 99.73(5) 3_556 . ? Cu2 Cu2 Cu1 78.385(16) 3_556 . ? O1 Cu2 O1 125.89(7) . 3_556 ? O4 Cu2 O1 49.52(8) . 3_556 ? N7 Cu2 O1 62.55(10) . 3_556 ? N8 Cu2 O1 121.53(9) . 3_556 ? O4 Cu2 O1 46.71(6) 3_556 3_556 ? Cu2 Cu2 O1 26.82(4) 3_556 3_556 ? Cu1 Cu2 O1 95.97(4) . 3_556 ? O1 Cu2 Cu1 127.16(9) . 3_556 ? O4 Cu2 Cu1 89.69(7) . 3_556 ? N7 Cu2 Cu1 51.15(9) . 3_556 ? N8 Cu2 Cu1 81.30(8) . 3_556 ? O4 Cu2 Cu1 39.89(5) 3_556 3_556 ? Cu2 Cu2 Cu1 53.653(14) 3_556 3_556 ? Cu1 Cu2 Cu1 132.039(14) . 3_556 ? O1 Cu2 Cu1 40.34(4) 3_556 3_556 ? N1 O1 Cu2 125.6(2) . . ? N1 O1 O4 90.26(18) . . ? Cu2 O1 O4 37.64(7) . . ? N4 O4 Cu2 123.63(19) . . ? N4 O4 O1 90.54(17) . . ? Cu2 O4 O1 37.15(7) . . ? C4 O5 C5 109.4(4) . . ? C2 N1 O1 116.9(3) . . ? C2 N1 Cu1 114.0(3) . . ? O1 N1 Cu1 128.8(2) . . ? C3 N2 N5 116.0(3) . . ? C3 N2 Cu1 116.8(3) . . ? N5 N2 Cu1 126.1(2) . . ? C7 N3 N6 116.5(3) . . ? C7 N3 Cu1 116.1(2) . . ? N6 N3 Cu1 126.0(2) . . ? C8 N4 O4 116.7(3) . . ? C8 N4 Cu1 115.3(2) . . ? O4 N4 Cu1 127.8(2) . . ? C4 N5 N2 111.6(3) . . ? C4 N5 C6 110.1(4) . . ? N2 N5 C6 109.1(3) . . ? C5 N6 N3 111.1(3) . . ? C5 N6 C6 108.8(4) . . ? N3 N6 C6 108.9(3) . . ? C10 N7 C14 118.6(3) . . ? C10 N7 Cu2 126.5(3) . . ? C14 N7 Cu2 114.9(2) . . ? C19 N8 C15 118.1(3) . . ? C19 N8 Cu2 126.9(3) . . ? C15 N8 Cu2 113.6(2) . . ? C2 C1 H2A 109.5 . . ? C2 C1 H2B 109.6 . . ? H2A C1 H2B 109.5 . . ? C2 C1 H2C 109.4 . . ? H2A C1 H2C 109.5 . . ? H2B C1 H2C 109.5 . . ? N1 C2 C1 124.5(4) . . ? N1 C2 C3 115.0(3) . . ? C1 C2 C3 120.5(4) . . ? O2 C3 N2 128.8(4) . . ? O2 C3 C2 120.0(4) . . ? N2 C3 C2 111.2(3) . . ? O3 C7 N3 127.8(3) . . ? O3 C7 C8 120.2(3) . . ? N3 C7 C8 112.0(3) . . ? N4 C8 C9 125.1(3) . . ? N4 C8 C7 114.0(3) . . ? C9 C8 C7 121.0(3) . . ? C8 C9 H9A 109.2 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.9 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N5 C6 N6 113.9(4) . . ? N5 C6 H6A 108.7 . . ? N6 C6 H6A 108.9 . . ? N5 C6 H6B 108.7 . . ? N6 C6 H6B 108.7 . . ? H6A C6 H6B 107.8 . . ? N5 C4 O5 112.5(4) . . ? N5 C4 H4A 109.3 . . ? O5 C4 H4A 109.0 . . ? N5 C4 H4B 108.8 . . ? O5 C4 H4B 109.1 . . ? H4A C4 H4B 108.0 . . ? N6 C5 O5 112.3(3) . . ? N6 C5 H5A 108.5 . . ? O5 C5 H5A 108.9 . . ? N6 C5 H5B 109.5 . . ? O5 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N7 C10 C11 122.2(4) . . ? N7 C10 H10A 118.5 . . ? C11 C10 H10A 119.3 . . ? C12 C11 C10 118.8(4) . . ? C12 C11 H11A 120.5 . . ? C10 C11 H11A 120.7 . . ? C11 C12 C13 119.3(4) . . ? C11 C12 H12A 120.5 . . ? C13 C12 H12A 120.2 . . ? C14 C13 C12 119.5(4) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 120.6 . . ? N7 C14 C13 121.5(3) . . ? N7 C14 C15 114.5(3) . . ? C13 C14 C15 124.0(3) . . ? N8 C15 C16 121.6(3) . . ? N8 C15 C14 114.6(3) . . ? C16 C15 C14 123.8(3) . . ? C17 C16 C15 119.3(4) . . ? C17 C16 H16A 120.6 . . ? C15 C16 H16A 120.1 . . ? C16 C17 C18 119.0(3) . . ? C16 C17 H17A 120.5 . . ? C18 C17 H17A 120.5 . . ? C19 C18 C17 118.7(4) . . ? C19 C18 H18A 121.0 . . ? C17 C18 H18A 120.3 . . ? N8 C19 C18 123.2(3) . . ? N8 C19 H19A 118.3 . . ? C18 C19 H19A 118.6 . . ? 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 N2 Cu1 Cu2 O1 -8.3(2) . . . . ? N3 Cu1 Cu2 O1 176.2(2) . . . . ? N1 Cu1 Cu2 O1 -4.08(17) . . . . ? N4 Cu1 Cu2 O1 168.37(17) . . . . ? Cu1 Cu1 Cu2 O1 110.43(12) 3_556 . . . ? N2 Cu1 Cu2 O4 -167.01(19) . . . . ? N3 Cu1 Cu2 O4 17.45(19) . . . . ? N1 Cu1 Cu2 O4 -162.83(17) . . . . ? N4 Cu1 Cu2 O4 9.62(15) . . . . ? Cu1 Cu1 Cu2 O4 -48.32(10) 3_556 . . . ? N2 Cu1 Cu2 N7 166.3(2) . . . . ? N3 Cu1 Cu2 N7 -9.2(2) . . . . ? N1 Cu1 Cu2 N7 170.49(18) . . . . ? N4 Cu1 Cu2 N7 -17.06(18) . . . . ? Cu1 Cu1 Cu2 N7 -75.01(14) 3_556 . . . ? N2 Cu1 Cu2 N8 16.6(2) . . . . ? N3 Cu1 Cu2 N8 -158.9(2) . . . . ? N1 Cu1 Cu2 N8 20.79(19) . . . . ? N4 Cu1 Cu2 N8 -166.76(18) . . . . ? Cu1 Cu1 Cu2 N8 135.30(14) 3_556 . . . ? N2 Cu1 Cu2 O4 -92.01(17) . . . 3_556 ? N3 Cu1 Cu2 O4 92.44(17) . . . 3_556 ? N1 Cu1 Cu2 O4 -87.83(14) . . . 3_556 ? N4 Cu1 Cu2 O4 84.62(13) . . . 3_556 ? Cu1 Cu1 Cu2 O4 26.68(5) 3_556 . . 3_556 ? N2 Cu1 Cu2 Cu2 -118.69(17) . . . 3_556 ? N3 Cu1 Cu2 Cu2 65.77(16) . . . 3_556 ? N1 Cu1 Cu2 Cu2 -114.51(13) . . . 3_556 ? N4 Cu1 Cu2 Cu2 57.94(11) . . . 3_556 ? Cu1 Cu1 Cu2 Cu2 0.0 3_556 . . 3_556 ? N2 Cu1 Cu2 O1 -139.04(17) . . . 3_556 ? N3 Cu1 Cu2 O1 45.41(16) . . . 3_556 ? N1 Cu1 Cu2 O1 -134.86(14) . . . 3_556 ? N4 Cu1 Cu2 O1 37.59(12) . . . 3_556 ? Cu1 Cu1 Cu2 O1 -20.35(4) 3_556 . . 3_556 ? N2 Cu1 Cu2 Cu1 -118.69(17) . . . 3_556 ? N3 Cu1 Cu2 Cu1 65.77(16) . . . 3_556 ? N1 Cu1 Cu2 Cu1 -114.51(13) . . . 3_556 ? N4 Cu1 Cu2 Cu1 57.94(11) . . . 3_556 ? O4 Cu2 O1 N1 23.4(3) . . . . ? N7 Cu2 O1 N1 -157.7(5) . . . . ? N8 Cu2 O1 N1 -158.1(3) . . . . ? O4 Cu2 O1 N1 107.2(3) 3_556 . . . ? Cu2 Cu2 O1 N1 74.0(3) 3_556 . . . ? Cu1 Cu2 O1 N1 5.7(2) . . . . ? O1 Cu2 O1 N1 74.0(3) 3_556 . . . ? Cu1 Cu2 O1 N1 124.8(3) 3_556 . . . ? N7 Cu2 O1 O4 178.9(6) . . . . ? N8 Cu2 O1 O4 178.52(12) . . . . ? O4 Cu2 O1 O4 83.84(10) 3_556 . . . ? Cu2 Cu2 O1 O4 50.68(9) 3_556 . . . ? Cu1 Cu2 O1 O4 -17.68(13) . . . . ? O1 Cu2 O1 O4 50.68(9) 3_556 . . . ? Cu1 Cu2 O1 O4 101.48(11) 3_556 . . . ? O1 Cu2 O4 N4 -30.8(3) . . . . ? N7 Cu2 O4 N4 149.5(3) . . . . ? N8 Cu2 O4 N4 156.0(5) . . . . ? O4 Cu2 O4 N4 -119.8(3) 3_556 . . . ? Cu2 Cu2 O4 N4 -119.8(3) 3_556 . . . ? Cu1 Cu2 O4 N4 -13.1(2) . . . . ? O1 Cu2 O4 N4 -155.3(3) 3_556 . . . ? Cu1 Cu2 O4 N4 -159.4(2) 3_556 . . . ? N7 Cu2 O4 O1 -179.76(13) . . . . ? N8 Cu2 O4 O1 -173.3(6) . . . . ? O4 Cu2 O4 O1 -89.09(11) 3_556 . . . ? Cu2 Cu2 O4 O1 -89.09(11) 3_556 . . . ? Cu1 Cu2 O4 O1 17.67(13) . . . . ? O1 Cu2 O4 O1 -124.51(9) 3_556 . . . ? Cu1 Cu2 O4 O1 -128.64(10) 3_556 . . . ? N1 O1 O4 N4 -6.4(3) . . . . ? Cu2 O1 O4 N4 154.8(2) . . . . ? N1 O1 O4 Cu2 -161.2(3) . . . . ? Cu2 O1 N1 C2 175.6(3) . . . . ? O4 O1 N1 C2 -170.4(3) . . . . ? Cu2 O1 N1 Cu1 -11.1(5) . . . . ? O4 O1 N1 Cu1 2.9(3) . . . . ? N2 Cu1 N1 C2 -3.7(3) . . . . ? N3 Cu1 N1 C2 -4(2) . . . . ? N4 Cu1 N1 C2 173.3(3) . . . . ? Cu2 Cu1 N1 C2 179.4(4) . . . . ? Cu1 Cu1 N1 C2 152.8(3) 3_556 . . . ? N2 Cu1 N1 O1 -177.1(3) . . . . ? N3 Cu1 N1 O1 -177(2) . . . . ? N4 Cu1 N1 O1 -0.1(3) . . . . ? Cu2 Cu1 N1 O1 6.0(3) . . . . ? Cu1 Cu1 N1 O1 -20.6(3) 3_556 . . . ? N3 Cu1 N2 C3 177.0(4) . . . . ? N1 Cu1 N2 C3 -3.0(4) . . . . ? N4 Cu1 N2 C3 -148.2(15) . . . . ? Cu2 Cu1 N2 C3 0.3(4) . . . . ? Cu1 Cu1 N2 C3 -37.3(5) 3_556 . . . ? N3 Cu1 N2 N5 9.6(4) . . . . ? N1 Cu1 N2 N5 -170.4(4) . . . . ? N4 Cu1 N2 N5 44.4(18) . . . . ? Cu2 Cu1 N2 N5 -167.1(3) . . . . ? Cu1 Cu1 N2 N5 155.3(3) 3_556 . . . ? N2 Cu1 N3 C7 -175.2(3) . . . . ? N1 Cu1 N3 C7 -175(2) . . . . ? N4 Cu1 N3 C7 7.7(3) . . . . ? Cu2 Cu1 N3 C7 1.5(4) . . . . ? Cu1 Cu1 N3 C7 29.0(4) 3_556 . . . ? N2 Cu1 N3 N6 -8.9(4) . . . . ? N1 Cu1 N3 N6 -9(3) . . . . ? N4 Cu1 N3 N6 174.0(4) . . . . ? Cu2 Cu1 N3 N6 167.8(3) . . . . ? Cu1 Cu1 N3 N6 -164.7(3) 3_556 . . . ? Cu2 O4 N4 C8 -159.6(3) . . . . ? O1 O4 N4 C8 -177.6(3) . . . . ? Cu2 O4 N4 Cu1 25.8(4) . . . . ? O1 O4 N4 Cu1 7.8(3) . . . . ? N2 Cu1 N4 C8 -37.9(17) . . . . ? N3 Cu1 N4 C8 -2.8(3) . . . . ? N1 Cu1 N4 C8 177.4(3) . . . . ? Cu2 Cu1 N4 C8 171.4(3) . . . . ? Cu1 Cu1 N4 C8 -154.1(3) 3_556 . . . ? N2 Cu1 N4 O4 136.8(15) . . . . ? N3 Cu1 N4 O4 171.8(3) . . . . ? N1 Cu1 N4 O4 -8.0(3) . . . . ? Cu2 Cu1 N4 O4 -14.0(2) . . . . ? Cu1 Cu1 N4 O4 20.5(2) 3_556 . . . ? C3 N2 N5 C4 -84.6(5) . . . . ? Cu1 N2 N5 C4 82.9(4) . . . . ? C3 N2 N5 C6 153.5(4) . . . . ? Cu1 N2 N5 C6 -39.0(5) . . . . ? C7 N3 N6 C5 82.9(4) . . . . ? Cu1 N3 N6 C5 -83.3(4) . . . . ? C7 N3 N6 C6 -157.2(4) . . . . ? Cu1 N3 N6 C6 36.5(5) . . . . ? O1 Cu2 N7 C10 171.5(5) . . . . ? O4 Cu2 N7 C10 -9.6(3) . . . . ? N8 Cu2 N7 C10 171.9(3) . . . . ? O4 Cu2 N7 C10 -93.4(3) 3_556 . . . ? Cu2 Cu2 N7 C10 -59.4(3) 3_556 . . . ? Cu1 Cu2 N7 C10 11.8(4) . . . . ? O1 Cu2 N7 C10 -54.3(3) 3_556 . . . ? Cu1 Cu2 N7 C10 -101.1(3) 3_556 . . . ? O1 Cu2 N7 C14 -10.5(7) . . . . ? O4 Cu2 N7 C14 168.5(3) . . . . ? N8 Cu2 N7 C14 -10.1(3) . . . . ? O4 Cu2 N7 C14 84.6(3) 3_556 . . . ? Cu2 Cu2 N7 C14 118.6(3) 3_556 . . . ? Cu1 Cu2 N7 C14 -170.23(19) . . . . ? O1 Cu2 N7 C14 123.7(3) 3_556 . . . ? Cu1 Cu2 N7 C14 76.9(2) 3_556 . . . ? O1 Cu2 N8 C19 0.9(3) . . . . ? O4 Cu2 N8 C19 174.4(5) . . . . ? N7 Cu2 N8 C19 -179.0(3) . . . . ? O4 Cu2 N8 C19 91.5(3) 3_556 . . . ? Cu2 Cu2 N8 C19 100.4(3) 3_556 . . . ? Cu1 Cu2 N8 C19 -19.0(4) . . . . ? O1 Cu2 N8 C19 132.3(3) 3_556 . . . ? Cu1 Cu2 N8 C19 129.1(3) 3_556 . . . ? O1 Cu2 N8 C15 -165.7(3) . . . . ? O4 Cu2 N8 C15 7.8(7) . . . . ? N7 Cu2 N8 C15 14.4(3) . . . . ? O4 Cu2 N8 C15 -75.2(3) 3_556 . . . ? Cu2 Cu2 N8 C15 -66.2(3) 3_556 . . . ? Cu1 Cu2 N8 C15 174.39(19) . . . . ? O1 Cu2 N8 C15 -34.4(3) 3_556 . . . ? Cu1 Cu2 N8 C15 -37.5(2) 3_556 . . . ? O1 N1 C2 C1 1.3(6) . . . . ? Cu1 N1 C2 C1 -172.9(4) . . . . ? O1 N1 C2 C3 -176.8(3) . . . . ? Cu1 N1 C2 C3 8.9(5) . . . . ? N5 N2 C3 O2 -1.3(8) . . . . ? Cu1 N2 C3 O2 -170.0(5) . . . . ? N5 N2 C3 C2 176.7(4) . . . . ? Cu1 N2 C3 C2 8.0(5) . . . . ? N1 C2 C3 O2 167.1(5) . . . . ? C1 C2 C3 O2 -11.1(7) . . . . ? N1 C2 C3 N2 -11.1(6) . . . . ? C1 C2 C3 N2 170.6(4) . . . . ? N6 N3 C7 O3 2.1(6) . . . . ? Cu1 N3 C7 O3 169.7(4) . . . . ? N6 N3 C7 C8 -178.1(3) . . . . ? Cu1 N3 C7 C8 -10.4(4) . . . . ? O4 N4 C8 C9 4.0(5) . . . . ? Cu1 N4 C8 C9 179.2(3) . . . . ? O4 N4 C8 C7 -177.2(3) . . . . ? Cu1 N4 C8 C7 -1.9(4) . . . . ? O3 C7 C8 N4 -172.2(4) . . . . ? N3 C7 C8 N4 8.0(5) . . . . ? O3 C7 C8 C9 6.7(6) . . . . ? N3 C7 C8 C9 -173.1(4) . . . . ? C4 N5 C6 N6 -50.4(5) . . . . ? N2 N5 C6 N6 72.4(4) . . . . ? C5 N6 C6 N5 49.9(4) . . . . ? N3 N6 C6 N5 -71.4(5) . . . . ? N2 N5 C4 O5 -65.6(5) . . . . ? C6 N5 C4 O5 55.6(5) . . . . ? C5 O5 C4 N5 -60.8(5) . . . . ? N3 N6 C5 O5 65.3(4) . . . . ? C6 N6 C5 O5 -54.6(4) . . . . ? C4 O5 C5 N6 60.7(4) . . . . ? C14 N7 C10 C11 -0.6(6) . . . . ? Cu2 N7 C10 C11 177.3(3) . . . . ? N7 C10 C11 C12 -1.0(7) . . . . ? C10 C11 C12 C13 1.7(7) . . . . ? C11 C12 C13 C14 -0.9(7) . . . . ? C10 N7 C14 C13 1.5(6) . . . . ? Cu2 N7 C14 C13 -176.7(3) . . . . ? C10 N7 C14 C15 -177.4(3) . . . . ? Cu2 N7 C14 C15 4.4(4) . . . . ? C12 C13 C14 N7 -0.7(6) . . . . ? C12 C13 C14 C15 178.0(4) . . . . ? C19 N8 C15 C16 -3.8(5) . . . . ? Cu2 N8 C15 C16 164.1(3) . . . . ? C19 N8 C15 C14 175.9(3) . . . . ? Cu2 N8 C15 C14 -16.2(4) . . . . ? N7 C14 C15 N8 7.8(5) . . . . ? C13 C14 C15 N8 -171.0(4) . . . . ? N7 C14 C15 C16 -172.4(4) . . . . ? C13 C14 C15 C16 8.7(6) . . . . ? N8 C15 C16 C17 2.1(6) . . . . ? C14 C15 C16 C17 -177.6(4) . . . . ? C15 C16 C17 C18 1.2(6) . . . . ? C16 C17 C18 C19 -2.7(6) . . . . ? C15 N8 C19 C18 2.3(6) . . . . ? Cu2 N8 C19 C18 -163.8(3) . . . . ? C17 C18 C19 N8 0.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.692 _refine_diff_density_min -0.716 _refine_diff_density_rms 0.090