Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Miguel Julve' _publ_contact_author_address ; Departament de Quimica Inorganica, Facultat de Quimica Universitat de Valencia Dr.Moliner, 50 Valencia Burjassot 46100 SPAIN ; _publ_contact_author_email MIGUEL.JULVE@UV.ES _publ_section_title ; Synthesis, crystal structures and magnetic properties of tricyanomethanide-containing polynuclear copper(II) complexes ; loop_ _publ_author_name 'Miguel Julve' 'Donatella Armentano' 'Laura Canadillas-Delgado' 'Fernando S. Delgado' 'F. Lloret' ; N.Marino ; 'D. Rillema' 'Catalina Ruiz-Perez' 'Consuelo Yuste' # Attachment 'CUPYIM_compound-1.cif' data_ull1350b _database_code_depnum_ccdc_archive 'CCDC 666745' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H7 Cu N9' _chemical_formula_weight 388.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' Cu Cu 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 '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 7.4889(4) _cell_length_b 11.0496(5) _cell_length_c 11.5924(5) _cell_angle_alpha 116.319(4) _cell_angle_beta 90.635(4) _cell_angle_gamma 108.260(4) _cell_volume 803.75(7) _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 needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 390 _exptl_absorpt_coefficient_mu 1.380 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mok\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7681 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.30 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3599 _reflns_number_gt 3324 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0311P)^2^+0.4532P] 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 3599 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0697 _refine_ls_wR_factor_gt 0.0675 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 Cu1 Cu 0.42695(3) 0.35207(2) 0.742574(19) 0.02553(8) Uani 1 1 d . . . N1 N 0.3356(2) 0.13783(16) 0.61227(14) 0.0272(3) Uani 1 1 d . . . N2 N 0.3112(2) 0.35686(17) 0.59090(15) 0.0322(3) Uani 1 1 d . . . C4 C 0.1713(3) -0.0387(2) 0.39571(19) 0.0349(4) Uani 1 1 d . . . N11 N 0.6143(2) 0.32983(18) 0.84801(15) 0.0336(3) Uani 1 1 d . . . N12 N 1.1908(2) 0.33344(18) 0.85129(16) 0.0343(3) Uani 1 1 d . . . N13 N 0.9104(5) 0.3396(5) 1.1874(3) 0.1251(16) Uani 1 1 d . . . N14 N 0.5454(3) 0.56340(18) 0.83649(17) 0.0433(4) Uani 1 1 d . . . N15 N 0.9217(3) 0.9940(2) 1.14833(18) 0.0468(5) Uani 1 1 d . . . N16 N 0.5622(4) 0.9471(3) 0.8137(3) 0.0690(7) Uani 1 1 d . . . C1 C 0.3486(3) 0.0327(2) 0.6362(2) 0.0334(4) Uani 1 1 d . . . C2 C 0.2733(3) -0.1110(2) 0.5431(2) 0.0387(4) Uani 1 1 d . . . C3 C 0.1831(3) -0.1468(2) 0.4221(2) 0.0389(4) Uani 1 1 d . . . C5 C 0.2482(2) 0.10225(19) 0.49333(17) 0.0278(4) Uani 1 1 d . . . C6 C 0.2396(3) 0.2280(2) 0.48590(17) 0.0292(4) Uani 1 1 d . . . N3 N 0.1592(3) 0.2385(2) 0.38864(17) 0.0374(4) Uani 1 1 d . . . C7 C 0.1783(4) 0.3788(3) 0.4330(2) 0.0469(5) Uani 1 1 d . . . C8 C 0.2738(4) 0.4523(2) 0.5585(2) 0.0442(5) Uani 1 1 d . . . C11 C 0.8993(3) 0.3243(2) 0.96259(18) 0.0292(4) Uani 1 1 d . . . C12 C 0.7402(2) 0.32690(18) 0.90176(17) 0.0265(3) Uani 1 1 d . . . C13 C 1.0609(3) 0.32915(18) 0.90279(17) 0.0268(4) Uani 1 1 d . . . C14 C 0.9039(4) 0.3315(4) 1.0861(2) 0.0590(7) Uani 1 1 d . . . C16 C 0.6053(3) 0.6870(2) 0.88469(18) 0.0322(4) Uani 1 1 d . . . C15 C 0.6745(3) 0.83628(19) 0.93894(18) 0.0323(4) Uani 1 1 d . . . C17 C 0.8104(3) 0.9228(2) 1.05446(19) 0.0329(4) Uani 1 1 d . . . C18 C 0.6121(3) 0.8993(2) 0.8713(2) 0.0401(5) Uani 1 1 d . . . H1 H 0.406(3) 0.060(2) 0.719(2) 0.042(6) Uiso 1 1 d . . . H8 H 0.319(3) 0.548(3) 0.617(2) 0.036(6) Uiso 1 1 d . . . H4 H 0.120(3) -0.057(2) 0.318(2) 0.040(6) Uiso 1 1 d . . . H7 H 0.137(3) 0.411(2) 0.382(2) 0.042(6) Uiso 1 1 d . . . H2 H 0.283(4) -0.185(3) 0.568(3) 0.055(7) Uiso 1 1 d . . . H5 H 0.095(4) 0.169(3) 0.316(3) 0.050(7) Uiso 1 1 d . . . H3 H 0.135(3) -0.242(3) 0.358(2) 0.047(7) 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 0.02481(12) 0.02624(12) 0.01943(11) 0.00707(8) -0.00424(8) 0.00721(8) N1 0.0242(7) 0.0296(7) 0.0222(7) 0.0081(6) 0.0009(6) 0.0090(6) N2 0.0361(9) 0.0326(8) 0.0231(7) 0.0105(6) -0.0041(6) 0.0107(6) C4 0.0320(10) 0.0373(10) 0.0228(9) 0.0058(8) 0.0009(7) 0.0092(8) N11 0.0285(8) 0.0433(9) 0.0262(8) 0.0123(7) -0.0005(6) 0.0154(7) N12 0.0291(8) 0.0401(9) 0.0300(8) 0.0121(7) 0.0030(7) 0.0142(7) N13 0.104(2) 0.279(5) 0.0662(18) 0.109(3) 0.0396(17) 0.120(3) N14 0.0503(11) 0.0292(9) 0.0357(9) 0.0109(7) -0.0175(8) 0.0029(7) N15 0.0504(11) 0.0411(10) 0.0334(10) 0.0133(8) -0.0090(8) 0.0036(8) N16 0.0755(16) 0.0817(17) 0.0752(16) 0.0534(14) 0.0032(13) 0.0352(13) C1 0.0310(10) 0.0376(10) 0.0319(10) 0.0163(8) 0.0033(8) 0.0129(8) C2 0.0375(11) 0.0349(10) 0.0458(12) 0.0193(9) 0.0087(9) 0.0150(8) C3 0.0363(11) 0.0316(10) 0.0349(11) 0.0062(8) 0.0050(8) 0.0090(8) C5 0.0221(8) 0.0340(9) 0.0216(8) 0.0090(7) 0.0028(6) 0.0090(7) C6 0.0248(9) 0.0368(9) 0.0199(8) 0.0102(7) -0.0009(7) 0.0082(7) N3 0.0386(9) 0.0438(9) 0.0227(8) 0.0126(7) -0.0053(7) 0.0108(7) C7 0.0567(14) 0.0517(13) 0.0370(12) 0.0243(10) -0.0042(10) 0.0204(11) C8 0.0582(14) 0.0361(11) 0.0361(11) 0.0160(9) -0.0063(10) 0.0160(10) C11 0.0256(9) 0.0372(9) 0.0264(9) 0.0149(8) 0.0017(7) 0.0135(7) C12 0.0254(9) 0.0278(8) 0.0210(8) 0.0076(7) 0.0019(7) 0.0089(7) C13 0.0281(9) 0.0238(8) 0.0225(8) 0.0060(7) -0.0047(7) 0.0094(7) C14 0.0437(13) 0.114(2) 0.0434(13) 0.0449(15) 0.0133(11) 0.0468(15) C16 0.0318(9) 0.0353(10) 0.0247(9) 0.0130(8) -0.0035(7) 0.0080(8) C15 0.0362(10) 0.0273(9) 0.0288(9) 0.0120(7) -0.0035(8) 0.0076(7) C17 0.0376(10) 0.0279(9) 0.0302(10) 0.0136(8) 0.0016(8) 0.0083(7) C18 0.0413(11) 0.0399(11) 0.0395(11) 0.0195(9) 0.0006(9) 0.0137(9) _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 N14 1.9624(17) . ? Cu1 N2 1.9808(15) . ? Cu1 N11 1.9917(16) . ? Cu1 N1 2.0359(15) . ? Cu1 N12 2.1931(17) 1_455 ? N1 C1 1.339(2) . ? N1 C5 1.350(2) . ? N2 C6 1.329(2) . ? N2 C8 1.365(3) . ? C4 C5 1.378(3) . ? C4 C3 1.385(3) . ? N11 C12 1.141(2) . ? N12 C13 1.146(2) . ? N12 Cu1 2.1931(17) 1_655 ? N13 C14 1.137(3) . ? N14 C16 1.146(2) . ? N15 C17 1.144(3) . ? N16 C18 1.138(3) . ? C1 C2 1.381(3) . ? C2 C3 1.378(3) . ? C5 C6 1.450(3) . ? C6 N3 1.339(2) . ? N3 C7 1.357(3) . ? C7 C8 1.361(3) . ? C11 C12 1.392(2) . ? C11 C14 1.398(3) . ? C11 C13 1.400(3) . ? C16 C15 1.386(3) . ? C15 C17 1.403(3) . ? C15 C18 1.413(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 N14 Cu1 N2 91.73(7) . . ? N14 Cu1 N11 91.95(7) . . ? N2 Cu1 N11 157.68(7) . . ? N14 Cu1 N1 166.88(7) . . ? N2 Cu1 N1 80.67(6) . . ? N11 Cu1 N1 91.21(6) . . ? N14 Cu1 N12 96.97(8) . 1_455 ? N2 Cu1 N12 102.40(7) . 1_455 ? N11 Cu1 N12 99.00(6) . 1_455 ? N1 Cu1 N12 95.11(6) . 1_455 ? C1 N1 C5 118.91(16) . . ? C1 N1 Cu1 126.08(13) . . ? C5 N1 Cu1 114.95(12) . . ? C6 N2 C8 106.53(16) . . ? C6 N2 Cu1 113.45(12) . . ? C8 N2 Cu1 139.98(14) . . ? C5 C4 C3 118.34(19) . . ? C12 N11 Cu1 170.56(16) . . ? C13 N12 Cu1 173.92(15) . 1_655 ? C16 N14 Cu1 174.79(16) . . ? N1 C1 C2 121.85(19) . . ? C3 C2 C1 119.00(19) . . ? C2 C3 C4 119.64(19) . . ? N1 C5 C4 122.25(18) . . ? N1 C5 C6 111.72(15) . . ? C4 C5 C6 125.98(17) . . ? N2 C6 N3 110.28(17) . . ? N2 C6 C5 119.20(16) . . ? N3 C6 C5 130.43(17) . . ? C6 N3 C7 107.78(17) . . ? N3 C7 C8 106.80(19) . . ? C7 C8 N2 108.61(19) . . ? C12 C11 C14 120.71(18) . . ? C12 C11 C13 118.05(16) . . ? C14 C11 C13 120.93(17) . . ? N11 C12 C11 177.1(2) . . ? N12 C13 C11 178.17(19) . . ? N13 C14 C11 178.8(4) . . ? N14 C16 C15 177.9(2) . . ? C16 C15 C17 121.10(17) . . ? C16 C15 C18 118.28(17) . . ? C17 C15 C18 120.54(17) . . ? N15 C17 C15 179.5(2) . . ? N16 C18 C15 178.1(3) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.441 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.050 data_compound2 _database_code_depnum_ccdc_archive 'CCDC 666746' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H8 Cu N8' _chemical_formula_weight 399.86 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' 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 7.7136(8) _cell_length_b 10.0610(10) _cell_length_c 12.6374(18) _cell_angle_alpha 107.932(6) _cell_angle_beta 104.904(6) _cell_angle_gamma 101.699(4) _cell_volume 858.26(17) _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 prism _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 402 _exptl_absorpt_coefficient_mu 1.293 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8488 _exptl_absorpt_correction_T_max 0.9121 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'X8APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12798 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 34.58 _reflns_number_total 5940 _reflns_number_gt 5256 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0397P)^2^+0.1693P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5940 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0798 _refine_ls_wR_factor_gt 0.0773 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Cu1 Cu 0.28985(2) 0.784534(15) 0.138383(11) 0.03378(5) Uani 1 1 d . . . N1 N 0.31071(15) 0.94111(11) 0.28739(8) 0.03310(19) Uani 1 1 d . . . N2 N 0.21655(15) 0.65803(11) 0.22341(8) 0.03262(19) Uani 1 1 d . . . C1 C 0.3641(2) 1.08567(14) 0.31255(12) 0.0416(3) Uani 1 1 d . . . H1A H 0.4078 1.1196 0.2607 0.050 Uiso 1 1 calc R . . C2 C 0.3566(2) 1.18602(16) 0.41288(13) 0.0495(3) Uani 1 1 d . . . H2A H 0.3945 1.2860 0.4287 0.059 Uiso 1 1 calc R . . C3 C 0.2919(3) 1.13470(18) 0.48881(13) 0.0556(4) Uani 1 1 d . . . H3A H 0.2817 1.1999 0.5557 0.067 Uiso 1 1 calc R . . C4 C 0.2422(2) 0.98665(17) 0.46605(11) 0.0474(3) Uani 1 1 d . . . H4A H 0.2020 0.9513 0.5183 0.057 Uiso 1 1 calc R . . C5 C 0.25307(18) 0.89129(14) 0.36386(9) 0.0334(2) Uani 1 1 d . . . C6 C 0.20814(17) 0.73081(14) 0.33025(10) 0.0334(2) Uani 1 1 d . . . C7 C 0.1662(2) 0.65808(17) 0.40192(12) 0.0462(3) Uani 1 1 d . . . H7A H 0.1608 0.7094 0.4755 0.055 Uiso 1 1 calc R . . C8 C 0.1324(2) 0.50753(18) 0.36185(14) 0.0517(4) Uani 1 1 d . . . H8A H 0.1043 0.4565 0.4085 0.062 Uiso 1 1 calc R . . C10 C 0.1826(2) 0.51254(15) 0.18550(12) 0.0410(3) Uani 1 1 d . . . H10A H 0.1874 0.4626 0.1115 0.049 Uiso 1 1 calc R . . N3 N 0.6138(2) 0.77545(14) 0.21350(12) 0.0479(3) Uani 1 1 d . . . N4 N 0.7419(2) 0.37888(14) 0.00835(10) 0.0454(3) Uani 1 1 d . . . N5 N 0.6383(3) 0.4314(2) 0.34543(18) 0.0849(6) Uani 1 1 d . . . C11 C 0.6724(2) 0.52897(15) 0.18563(11) 0.0382(3) Uani 1 1 d . . . C12 C 0.64378(18) 0.66536(14) 0.19855(10) 0.0362(2) Uani 1 1 d . . . C13 C 0.70970(19) 0.44789(14) 0.08766(10) 0.0369(2) Uani 1 1 d . . . C14 C 0.6545(3) 0.47219(18) 0.27257(14) 0.0507(3) Uani 1 1 d . . . N6 N 0.33206(19) 0.92014(14) 0.05586(10) 0.0431(3) Uani 1 1 d . . . N7 N 0.1430(3) 0.84922(16) -0.32290(12) 0.0619(4) Uani 1 1 d . . . N8 N 0.0696(2) 1.22410(15) -0.06358(12) 0.0510(3) Uani 1 1 d . . . C15 C 0.18093(19) 0.99740(14) -0.10944(10) 0.0357(2) Uani 1 1 d . . . C16 C 0.26266(19) 0.95497(14) -0.01910(11) 0.0360(2) Uani 1 1 d . . . C17 C 0.1629(2) 0.91664(15) -0.22697(12) 0.0409(3) Uani 1 1 d . . . C18 C 0.12125(19) 1.12329(14) -0.08302(11) 0.0367(2) Uani 1 1 d . . . C9 C 0.1407(2) 0.43427(16) 0.25305(14) 0.0490(3) Uani 1 1 d . . . H9A H 0.1184 0.3332 0.2251 0.059 Uiso 1 1 calc R . . 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 0.05275(10) 0.03270(8) 0.02554(7) 0.01441(6) 0.02066(6) 0.01838(7) N1 0.0437(5) 0.0329(5) 0.0265(4) 0.0123(4) 0.0155(4) 0.0136(4) N2 0.0410(5) 0.0331(5) 0.0276(4) 0.0140(4) 0.0142(4) 0.0123(4) C1 0.0561(8) 0.0347(6) 0.0366(6) 0.0150(5) 0.0182(5) 0.0137(5) C2 0.0686(10) 0.0346(6) 0.0389(6) 0.0080(5) 0.0150(6) 0.0164(6) C3 0.0837(12) 0.0482(8) 0.0326(6) 0.0063(6) 0.0228(7) 0.0259(8) C4 0.0679(9) 0.0502(8) 0.0295(5) 0.0136(5) 0.0250(6) 0.0211(7) C5 0.0406(6) 0.0377(6) 0.0237(4) 0.0117(4) 0.0129(4) 0.0133(5) C6 0.0387(6) 0.0380(6) 0.0258(4) 0.0148(4) 0.0125(4) 0.0108(5) C7 0.0593(8) 0.0507(8) 0.0328(6) 0.0214(5) 0.0203(6) 0.0111(6) C8 0.0632(9) 0.0516(8) 0.0471(7) 0.0317(7) 0.0204(7) 0.0098(7) C10 0.0517(7) 0.0348(6) 0.0387(6) 0.0150(5) 0.0175(5) 0.0133(5) N3 0.0616(8) 0.0444(6) 0.0531(7) 0.0234(5) 0.0333(6) 0.0230(6) N4 0.0694(8) 0.0444(6) 0.0315(5) 0.0158(4) 0.0223(5) 0.0275(6) N5 0.1249(16) 0.1039(15) 0.0785(11) 0.0650(11) 0.0636(12) 0.0583(13) C11 0.0518(7) 0.0409(6) 0.0307(5) 0.0154(5) 0.0202(5) 0.0213(5) C12 0.0420(6) 0.0416(6) 0.0306(5) 0.0143(5) 0.0190(5) 0.0152(5) C13 0.0469(7) 0.0386(6) 0.0285(5) 0.0131(4) 0.0131(5) 0.0187(5) C14 0.0716(10) 0.0538(8) 0.0472(7) 0.0271(7) 0.0331(7) 0.0324(8) N6 0.0640(7) 0.0457(6) 0.0378(5) 0.0249(5) 0.0285(5) 0.0258(5) N7 0.1011(12) 0.0515(8) 0.0418(6) 0.0187(6) 0.0335(7) 0.0285(8) N8 0.0627(8) 0.0494(7) 0.0508(7) 0.0195(6) 0.0259(6) 0.0288(6) C15 0.0482(7) 0.0366(6) 0.0327(5) 0.0182(4) 0.0203(5) 0.0182(5) C16 0.0474(6) 0.0360(6) 0.0362(5) 0.0189(5) 0.0242(5) 0.0160(5) C17 0.0589(8) 0.0362(6) 0.0377(6) 0.0196(5) 0.0229(6) 0.0183(6) C18 0.0425(6) 0.0401(6) 0.0342(5) 0.0173(5) 0.0180(5) 0.0152(5) C9 0.0597(9) 0.0366(7) 0.0531(8) 0.0233(6) 0.0182(7) 0.0114(6) _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 N6 1.9813(11) . ? Cu1 N4 1.9818(12) 2_665 ? Cu1 N2 1.9892(10) . ? Cu1 N1 1.9920(10) . ? Cu1 N3 2.4657(14) . ? N1 C1 1.3383(16) . ? N1 C5 1.3460(15) . ? N2 C10 1.3375(16) . ? N2 C6 1.3487(15) . ? C1 C2 1.3797(19) . ? C2 C3 1.372(2) . ? C3 C4 1.377(2) . ? C4 C5 1.3859(17) . ? C5 C6 1.4773(17) . ? C6 C7 1.3868(16) . ? C7 C8 1.385(2) . ? C8 C9 1.370(2) . ? C10 C9 1.3807(19) . ? N3 C12 1.1460(18) . ? N4 C13 1.1479(16) . ? N4 Cu1 1.9818(12) 2_665 ? N5 C14 1.141(2) . ? C11 C13 1.3918(17) . ? C11 C12 1.4007(18) . ? C11 C14 1.4091(19) . ? N6 C16 1.1517(16) . ? N7 C17 1.1440(18) . ? N8 C18 1.1440(18) . ? C15 C16 1.3864(17) . ? C15 C18 1.4081(18) . ? C15 C17 1.4108(17) . ? 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 N6 Cu1 N4 88.13(5) . 2_665 ? N6 Cu1 N2 171.94(5) . . ? N4 Cu1 N2 95.79(5) 2_665 . ? N6 Cu1 N1 94.51(5) . . ? N4 Cu1 N1 176.76(5) 2_665 . ? N2 Cu1 N1 81.35(4) . . ? N6 Cu1 N3 99.71(5) . . ? N4 Cu1 N3 86.64(5) 2_665 . ? N2 Cu1 N3 87.58(4) . . ? N1 Cu1 N3 94.75(4) . . ? C1 N1 C5 119.30(10) . . ? C1 N1 Cu1 126.00(8) . . ? C5 N1 Cu1 114.56(8) . . ? C10 N2 C6 119.29(10) . . ? C10 N2 Cu1 125.90(8) . . ? C6 N2 Cu1 114.77(8) . . ? N1 C1 C2 122.21(12) . . ? C3 C2 C1 118.40(14) . . ? C2 C3 C4 120.03(13) . . ? C3 C4 C5 118.85(13) . . ? N1 C5 C4 121.14(12) . . ? N1 C5 C6 114.50(10) . . ? C4 C5 C6 124.35(11) . . ? N2 C6 C7 121.38(12) . . ? N2 C6 C5 114.39(10) . . ? C7 C6 C5 124.20(11) . . ? C8 C7 C6 118.72(13) . . ? C9 C8 C7 119.57(12) . . ? N2 C10 C9 121.94(13) . . ? C12 N3 Cu1 120.83(11) . . ? C13 N4 Cu1 160.11(13) . 2_665 ? C13 C11 C12 121.54(11) . . ? C13 C11 C14 120.36(12) . . ? C12 C11 C14 118.04(11) . . ? N3 C12 C11 175.68(13) . . ? N4 C13 C11 178.28(14) . . ? N5 C14 C11 177.12(19) . . ? C16 N6 Cu1 144.72(12) . . ? C16 C15 C18 119.85(11) . . ? C16 C15 C17 119.82(12) . . ? C18 C15 C17 120.30(11) . . ? N6 C16 C15 179.41(15) . . ? N7 C17 C15 178.03(18) . . ? N8 C18 C15 178.60(16) . . ? C8 C9 C10 119.09(14) . . ? _diffrn_measured_fraction_theta_max 0.810 _diffrn_reflns_theta_full 34.58 _diffrn_measured_fraction_theta_full 0.810 _refine_diff_density_max 0.364 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.046 # Attachment 'CUBPZ_compound-3.CIF' data_compound3 _database_code_depnum_ccdc_archive 'CCDC 666747' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H12 Cu2 N20' _chemical_formula_weight 803.70 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' 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 9.998(3) _cell_length_b 12.583(2) _cell_length_c 14.391(3) _cell_angle_alpha 97.370(10) _cell_angle_beta 106.10(2) _cell_angle_gamma 93.20(2) _cell_volume 1717.1(7) _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 cube _exptl_crystal_colour dark-green _exptl_crystal_size_max 0.044 _exptl_crystal_size_mid 0.040 _exptl_crystal_size_min 0.035 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.296 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.940 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_process_details psi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'R3m/V automatic four-circle diffractometer' _diffrn_measurement_method omega/2-theta-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.2 _diffrn_reflns_number 6447 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.05 _reflns_number_total 6067 _reflns_number_gt 4866 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker P3' _computing_cell_refinement 'Bruker P3' _computing_data_reduction 'Bruker XDISK' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL NT Bruker XP' _computing_publication_material 'SHELXTL NT Package Bruker' _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^)+(0.1033P)^2^+0.1253P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6067 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1470 _refine_ls_wR_factor_gt 0.1366 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Cu1 Cu 0.22699(4) 0.82807(3) 0.69518(3) 0.03384(16) Uani 1 1 d . . . Cu2 Cu 0.12603(4) 0.52658(3) 0.21100(3) 0.03372(16) Uani 1 1 d . . . N1 N 0.1017(3) 0.9493(2) 0.6675(2) 0.0351(6) Uani 1 1 d . . . N2 N -0.0313(4) 1.1330(3) 0.6282(3) 0.0575(10) Uani 1 1 d . . . N3 N 0.3569(3) 0.9519(2) 0.7777(2) 0.0389(7) Uani 1 1 d . . . N4 N 0.5258(4) 1.1385(3) 0.8715(4) 0.0808(14) Uani 1 1 d . . . N5 N 0.2323(3) 0.4097(2) 0.2708(2) 0.0341(6) Uani 1 1 d . . . N6 N 0.3632(4) 0.2332(3) 0.3331(3) 0.0610(10) Uani 1 1 d . . . N7 N -0.0074(3) 0.3976(2) 0.1379(2) 0.0322(6) Uani 1 1 d . . . N8 N -0.1784(4) 0.2077(3) 0.0598(3) 0.0545(9) Uani 1 1 d . . . N9 N 0.3338(3) 0.7176(2) 0.7633(2) 0.0453(8) Uani 1 1 d . . . N10 N 0.7002(4) 0.5407(3) 0.9112(3) 0.0680(11) Uani 1 1 d . . . N11 N 0.2796(5) 0.3825(3) 0.8049(4) 0.0876(15) Uani 1 1 d . . . N12 N 0.0760(3) 0.7165(2) 0.6199(2) 0.0439(7) Uani 1 1 d . . . N13 N -0.3451(5) 0.5577(6) 0.4444(4) 0.131(3) Uani 1 1 d . . . N14 N 0.0176(4) 0.5483(3) 0.3286(3) 0.0507(8) Uani 1 1 d . . . N15 N 0.3100(3) 0.8305(2) 0.5708(2) 0.0427(7) Uani 1 1 d . . . N16 N 0.6516(5) 0.8703(5) 0.4337(4) 0.111(2) Uani 1 1 d . . . N17 N 0.2699(3) 0.6440(3) 0.2879(2) 0.0440(7) Uani 1 1 d . . . N18 N 0.0315(3) 0.6276(2) 0.1292(2) 0.0464(8) Uani 1 1 d . . . N19 N -0.3068(7) 0.8031(5) -0.0434(4) 0.123(2) Uani 1 1 d . . . N20 N 0.0788(6) 0.9742(3) 0.1545(4) 0.0977(17) Uani 1 1 d . . . C1 C -0.0293(4) 0.9424(3) 0.6111(3) 0.0427(9) Uani 1 1 d . . . H1 H -0.0774 0.8751 0.5843 0.051 Uiso 1 1 calc R . . C2 C -0.0953(4) 1.0345(3) 0.5918(3) 0.0575(11) Uani 1 1 d . . . H2 H -0.1872 1.0274 0.5521 0.069 Uiso 1 1 calc R . . C3 C 0.0988(4) 1.1385(3) 0.6840(3) 0.0470(9) Uani 1 1 d . . . H3 H 0.1470 1.2059 0.7099 0.056 Uiso 1 1 calc R . . C4 C 0.1666(3) 1.0477(3) 0.7055(2) 0.0347(7) Uani 1 1 d . . . C5 C 0.3097(4) 1.0491(3) 0.7680(3) 0.0391(8) Uani 1 1 d . . . C6 C 0.4865(4) 0.9482(3) 0.8342(3) 0.0591(12) Uani 1 1 d . . . H6 H 0.5215 0.8821 0.8427 0.071 Uiso 1 1 calc R . . C7 C 0.5693(5) 1.0422(4) 0.8802(4) 0.0769(16) Uani 1 1 d . . . H7 H 0.6595 1.0374 0.9191 0.092 Uiso 1 1 calc R . . C8 C 0.3965(5) 1.1413(3) 0.8158(4) 0.0642(13) Uani 1 1 d . . . H8 H 0.3623 1.2079 0.8085 0.077 Uiso 1 1 calc R . . C9 C 0.3579(4) 0.4208(3) 0.3346(3) 0.0415(8) Uani 1 1 d . . . H9 H 0.4037 0.4893 0.3590 0.050 Uiso 1 1 calc R . . C10 C 0.4218(4) 0.3318(3) 0.3653(3) 0.0537(10) Uani 1 1 d . . . H10 H 0.5098 0.3423 0.4106 0.064 Uiso 1 1 calc R . . C11 C 0.2374(4) 0.2229(3) 0.2688(3) 0.0507(10) Uani 1 1 d . . . H11 H 0.1924 0.1541 0.2445 0.061 Uiso 1 1 calc R . . C12 C 0.1705(4) 0.3099(3) 0.2366(2) 0.0351(7) Uani 1 1 d . . . C13 C 0.0328(4) 0.3035(3) 0.1653(3) 0.0360(8) Uani 1 1 d . . . C14 C -0.1315(4) 0.3968(3) 0.0725(3) 0.0411(8) Uani 1 1 d . . . H14 H -0.1619 0.4610 0.0527 0.049 Uiso 1 1 calc R . . C15 C -0.2151(4) 0.3020(3) 0.0337(3) 0.0507(10) Uani 1 1 d . . . H15 H -0.3006 0.3040 -0.0124 0.061 Uiso 1 1 calc R . . C16 C -0.0548(4) 0.2096(3) 0.1241(3) 0.0487(10) Uani 1 1 d . . . H16 H -0.0249 0.1448 0.1429 0.058 Uiso 1 1 calc R . . C17 C 0.4410(4) 0.5554(3) 0.8306(3) 0.0429(9) Uani 1 1 d . . . C18 C 0.3858(4) 0.6455(3) 0.7947(3) 0.0387(8) Uani 1 1 d . . . C19 C 0.5837(4) 0.5507(3) 0.8764(3) 0.0479(9) Uani 1 1 d . . . C20 C 0.3506(4) 0.4607(3) 0.8157(3) 0.0539(11) Uani 1 1 d . . . C21 C -0.0899(4) 0.6119(3) 0.4637(3) 0.0411(8) Uani 1 1 d . . . C22 C -0.0018(4) 0.6694(3) 0.5495(3) 0.0374(8) Uani 1 1 d . . . C23 C -0.2301(5) 0.5827(5) 0.4534(3) 0.0725(15) Uani 1 1 d . . . C24 C -0.0316(4) 0.5772(3) 0.3886(3) 0.0395(8) Uani 1 1 d . . . C25 C 0.4090(4) 0.7891(3) 0.4263(3) 0.0417(8) Uani 1 1 d . . . C26 C 0.3547(4) 0.8130(3) 0.5060(3) 0.0362(8) Uani 1 1 d . . . C27 C 0.5422(5) 0.8354(4) 0.4298(3) 0.0722(15) Uani 1 1 d . . . C28 C 0.3343(4) 0.7103(3) 0.3492(3) 0.0387(8) Uani 1 1 d . . . C29 C -0.0731(5) 0.7980(3) 0.0791(3) 0.0481(9) Uani 1 1 d . . . C30 C -0.0206(4) 0.7028(3) 0.1057(3) 0.0394(8) Uani 1 1 d . . . C31 C -0.2037(6) 0.7986(4) 0.0109(4) 0.0705(14) Uani 1 1 d . . . C32 C 0.0117(6) 0.8950(3) 0.1195(3) 0.0620(12) 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 0.0355(3) 0.0180(2) 0.0407(3) 0.00185(17) 0.00016(19) 0.00307(17) Cu2 0.0355(3) 0.0184(2) 0.0399(3) 0.00468(17) -0.00116(19) 0.00088(17) N1 0.0348(16) 0.0245(14) 0.0403(15) 0.0034(12) 0.0025(13) 0.0028(12) N2 0.050(2) 0.0283(18) 0.081(3) 0.0112(17) -0.0046(18) 0.0115(15) N3 0.0400(17) 0.0244(15) 0.0427(16) 0.0020(12) -0.0029(13) 0.0047(12) N4 0.056(2) 0.035(2) 0.115(4) -0.002(2) -0.028(2) -0.0035(18) N5 0.0311(15) 0.0292(15) 0.0394(15) 0.0047(12) 0.0051(12) 0.0059(12) N6 0.056(2) 0.041(2) 0.080(3) 0.0176(18) 0.0027(19) 0.0161(17) N7 0.0327(15) 0.0244(14) 0.0363(15) 0.0040(11) 0.0048(12) 0.0037(11) N8 0.050(2) 0.0299(18) 0.072(2) -0.0087(16) 0.0085(18) -0.0075(15) N9 0.0465(18) 0.0285(16) 0.0530(19) 0.0098(14) -0.0001(15) 0.0026(14) N10 0.053(2) 0.067(3) 0.080(3) 0.033(2) 0.000(2) 0.0095(19) N11 0.065(3) 0.030(2) 0.153(5) 0.024(2) 0.003(3) 0.0007(19) N12 0.0401(17) 0.0308(17) 0.0522(19) -0.0026(14) 0.0039(15) -0.0010(14) N13 0.055(3) 0.208(7) 0.103(4) -0.064(4) 0.031(3) -0.049(4) N14 0.049(2) 0.049(2) 0.0525(19) -0.0003(16) 0.0159(17) 0.0012(16) N15 0.0404(18) 0.0385(18) 0.0457(17) 0.0047(14) 0.0071(15) 0.0049(14) N16 0.089(4) 0.130(5) 0.101(4) -0.036(3) 0.043(3) -0.065(3) N17 0.0431(18) 0.0314(17) 0.0503(18) -0.0002(15) 0.0059(15) -0.0028(14) N18 0.0469(19) 0.0270(17) 0.0574(19) 0.0095(14) 0.0008(15) 0.0023(14) N19 0.125(5) 0.086(4) 0.122(5) 0.031(3) -0.036(4) 0.037(4) N20 0.116(4) 0.024(2) 0.144(5) 0.006(2) 0.026(3) 0.001(2) C1 0.0356(19) 0.0248(18) 0.057(2) 0.0012(16) -0.0012(17) 0.0006(15) C2 0.044(2) 0.038(2) 0.073(3) 0.009(2) -0.012(2) 0.0080(18) C3 0.050(2) 0.0205(17) 0.062(2) 0.0079(16) 0.0007(19) 0.0038(16) C4 0.0329(18) 0.0232(17) 0.0426(19) 0.0018(14) 0.0041(15) 0.0003(13) C5 0.042(2) 0.0240(17) 0.0437(19) 0.0022(14) 0.0014(16) 0.0046(15) C6 0.046(2) 0.031(2) 0.079(3) 0.000(2) -0.016(2) 0.0088(17) C7 0.052(3) 0.040(3) 0.101(4) -0.002(2) -0.032(3) -0.001(2) C8 0.054(3) 0.0206(19) 0.093(3) 0.000(2) -0.016(2) 0.0034(17) C9 0.039(2) 0.0320(19) 0.046(2) 0.0045(16) 0.0020(16) 0.0023(15) C10 0.044(2) 0.049(3) 0.059(2) 0.014(2) -0.0037(19) 0.0133(19) C11 0.052(2) 0.0251(19) 0.067(3) 0.0105(18) 0.003(2) 0.0071(17) C12 0.0393(19) 0.0227(17) 0.0423(19) 0.0055(14) 0.0094(15) 0.0045(14) C13 0.0387(19) 0.0240(17) 0.0435(19) 0.0014(14) 0.0103(15) 0.0032(14) C14 0.041(2) 0.0318(19) 0.0424(19) 0.0016(15) 0.0009(16) 0.0039(16) C15 0.039(2) 0.046(2) 0.052(2) -0.0070(19) -0.0045(17) -0.0037(18) C16 0.049(2) 0.0234(18) 0.066(3) 0.0007(17) 0.008(2) -0.0033(16) C17 0.043(2) 0.0259(18) 0.056(2) 0.0098(16) 0.0066(18) 0.0037(15) C18 0.0384(19) 0.0270(18) 0.0440(19) 0.0039(15) 0.0020(16) -0.0003(15) C19 0.050(2) 0.036(2) 0.054(2) 0.0176(18) 0.0045(19) 0.0046(17) C20 0.047(2) 0.029(2) 0.079(3) 0.0121(19) 0.003(2) 0.0143(18) C21 0.0348(19) 0.037(2) 0.045(2) -0.0033(16) 0.0059(16) -0.0024(15) C22 0.040(2) 0.0202(17) 0.052(2) 0.0029(16) 0.0144(18) 0.0027(15) C23 0.053(3) 0.095(4) 0.057(3) -0.028(3) 0.018(2) -0.018(3) C24 0.0356(19) 0.0299(18) 0.048(2) 0.0058(16) 0.0043(17) -0.0006(15) C25 0.038(2) 0.037(2) 0.045(2) 0.0016(16) 0.0083(16) -0.0082(16) C26 0.0342(18) 0.0199(16) 0.045(2) 0.0054(14) -0.0036(16) 0.0012(13) C27 0.069(3) 0.080(4) 0.060(3) -0.017(2) 0.026(2) -0.033(3) C28 0.039(2) 0.0283(18) 0.047(2) 0.0085(16) 0.0094(17) 0.0014(15) C29 0.062(3) 0.0262(19) 0.055(2) 0.0105(17) 0.010(2) 0.0119(18) C30 0.046(2) 0.0269(19) 0.0410(19) 0.0061(15) 0.0048(16) 0.0032(16) C31 0.086(4) 0.040(2) 0.075(3) 0.015(2) -0.001(3) 0.025(2) C32 0.089(4) 0.029(2) 0.072(3) 0.013(2) 0.024(3) 0.021(2) _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 N12 1.973(3) . ? Cu1 N3 1.992(3) . ? Cu1 N9 1.992(3) . ? Cu1 N1 2.036(3) . ? Cu1 N15 2.174(3) . ? Cu2 N18 1.948(3) . ? Cu2 N17 1.984(3) . ? Cu2 N5 2.006(3) . ? Cu2 N7 2.016(3) . ? Cu2 N14 2.246(3) . ? N1 C1 1.327(4) . ? N1 C4 1.340(4) . ? N2 C3 1.318(5) . ? N2 C2 1.334(5) . ? N3 C6 1.333(5) . ? N3 C5 1.345(4) . ? N4 C7 1.318(6) . ? N4 C8 1.324(5) . ? N5 C9 1.322(4) . ? N5 C12 1.336(4) . ? N6 C10 1.311(5) . ? N6 C11 1.327(5) . ? N7 C14 1.332(4) . ? N7 C13 1.342(4) . ? N8 C16 1.320(5) . ? N8 C15 1.330(5) . ? N9 C18 1.151(5) . ? N10 C19 1.154(5) . ? N11 C20 1.148(6) . ? N12 C22 1.158(5) . ? N13 C23 1.143(6) . ? N14 C24 1.138(5) . ? N15 C26 1.144(5) . ? N16 C27 1.139(6) . ? N17 C28 1.151(5) . ? N18 C30 1.150(5) . ? N19 C31 1.117(7) . ? N20 C32 1.143(6) . ? C1 C2 1.386(5) . ? C3 C4 1.386(5) . ? C4 C5 1.462(5) . ? C5 C8 1.386(5) . ? C6 C7 1.381(6) . ? C9 C10 1.381(5) . ? C11 C12 1.379(5) . ? C12 C13 1.462(5) . ? C13 C16 1.390(5) . ? C14 C15 1.375(5) . ? C17 C18 1.385(5) . ? C17 C19 1.405(6) . ? C17 C20 1.411(6) . ? C21 C22 1.386(5) . ? C21 C23 1.391(6) . ? C21 C24 1.398(5) . ? C25 C28 1.395(5) . ? C25 C26 1.406(5) . ? C25 C27 1.409(6) . ? C29 C30 1.390(5) . ? C29 C31 1.400(7) . ? C29 C32 1.406(6) . ? 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 N12 Cu1 N3 171.31(12) . . ? N12 Cu1 N9 90.61(13) . . ? N3 Cu1 N9 94.28(12) . . ? N12 Cu1 N1 92.73(12) . . ? N3 Cu1 N1 80.37(11) . . ? N9 Cu1 N1 161.21(13) . . ? N12 Cu1 N15 91.43(13) . . ? N3 Cu1 N15 94.62(12) . . ? N9 Cu1 N15 101.55(13) . . ? N1 Cu1 N15 96.85(11) . . ? N18 Cu2 N17 90.08(13) . . ? N18 Cu2 N5 168.46(13) . . ? N17 Cu2 N5 94.14(13) . . ? N18 Cu2 N7 94.96(12) . . ? N17 Cu2 N7 174.68(12) . . ? N5 Cu2 N7 80.59(11) . . ? N18 Cu2 N14 98.85(14) . . ? N17 Cu2 N14 88.92(13) . . ? N5 Cu2 N14 91.98(12) . . ? N7 Cu2 N14 91.98(12) . . ? C1 N1 C4 117.7(3) . . ? C1 N1 Cu1 128.1(2) . . ? C4 N1 Cu1 113.9(2) . . ? C3 N2 C2 116.4(3) . . ? C6 N3 C5 118.0(3) . . ? C6 N3 Cu1 126.9(3) . . ? C5 N3 Cu1 114.9(2) . . ? C7 N4 C8 116.4(4) . . ? C9 N5 C12 117.9(3) . . ? C9 N5 Cu2 127.1(2) . . ? C12 N5 Cu2 114.9(2) . . ? C10 N6 C11 116.2(3) . . ? C14 N7 C13 118.1(3) . . ? C14 N7 Cu2 127.7(2) . . ? C13 N7 Cu2 114.1(2) . . ? C16 N8 C15 116.1(3) . . ? C18 N9 Cu1 172.4(3) . . ? C22 N12 Cu1 155.1(3) . . ? C24 N14 Cu2 168.5(3) . . ? C26 N15 Cu1 168.0(3) . . ? C28 N17 Cu2 162.6(3) . . ? C30 N18 Cu2 161.2(3) . . ? N1 C1 C2 120.7(3) . . ? N2 C2 C1 122.1(4) . . ? N2 C3 C4 122.6(3) . . ? N1 C4 C3 120.4(3) . . ? N1 C4 C5 114.8(3) . . ? C3 C4 C5 124.9(3) . . ? N3 C5 C8 119.6(3) . . ? N3 C5 C4 115.4(3) . . ? C8 C5 C4 125.0(3) . . ? N3 C6 C7 120.3(4) . . ? N4 C7 C6 122.8(4) . . ? N4 C8 C5 122.8(4) . . ? N5 C9 C10 120.7(3) . . ? N6 C10 C9 122.6(4) . . ? N6 C11 C12 122.7(4) . . ? N5 C12 C11 119.9(3) . . ? N5 C12 C13 114.9(3) . . ? C11 C12 C13 125.2(3) . . ? N7 C13 C16 119.3(3) . . ? N7 C13 C12 115.3(3) . . ? C16 C13 C12 125.4(3) . . ? N7 C14 C15 120.7(3) . . ? N8 C15 C14 122.6(4) . . ? N8 C16 C13 123.2(4) . . ? C18 C17 C19 123.7(3) . . ? C18 C17 C20 118.5(3) . . ? C19 C17 C20 117.7(3) . . ? N9 C18 C17 176.7(4) . . ? N10 C19 C17 176.0(5) . . ? N11 C20 C17 178.3(5) . . ? C22 C21 C23 121.9(4) . . ? C22 C21 C24 117.9(3) . . ? C23 C21 C24 120.1(3) . . ? N12 C22 C21 177.4(4) . . ? N13 C23 C21 179.3(6) . . ? N14 C24 C21 178.8(4) . . ? C28 C25 C26 118.1(3) . . ? C28 C25 C27 121.3(4) . . ? C26 C25 C27 120.3(3) . . ? N15 C26 C25 178.8(4) . . ? N16 C27 C25 178.0(7) . . ? N17 C28 C25 177.4(4) . . ? C30 C29 C31 121.9(4) . . ? C30 C29 C32 118.0(4) . . ? C31 C29 C32 120.1(4) . . ? N18 C30 C29 175.6(4) . . ? N19 C31 C29 177.4(6) . . ? N20 C32 C29 177.9(6) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.944 _refine_diff_density_min -1.206 _refine_diff_density_rms 0.114 # Attachment 'CUTERPY_compound-4.CIF' data_compound4 _database_code_depnum_ccdc_archive 'CCDC 666748' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H11 Cu N9' _chemical_formula_weight 476.95 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' 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' 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 7.4688(4) _cell_length_b 13.2245(10) _cell_length_c 21.0460(15) _cell_angle_alpha 90.00 _cell_angle_beta 93.657(2) _cell_angle_gamma 90.00 _cell_volume 2074.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour dark-green _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 1.085 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8455 _exptl_absorpt_correction_T_max 0.8992 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'X8APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44419 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.26 _reflns_number_total 4601 _reflns_number_gt 3916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^+0.6505P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4601 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0743 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _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 0.37048(2) 0.373191(15) 0.117986(9) 0.03350(8) Uani 1 1 d . . . N1 N 0.32580(18) 0.23429(11) 0.07961(7) 0.0377(3) Uani 1 1 d . . . N2 N 0.27577(16) 0.41084(11) 0.03319(6) 0.0326(3) Uani 1 1 d . . . N3 N 0.40623(18) 0.52558(11) 0.12192(7) 0.0378(3) Uani 1 1 d . . . C1 C 0.3558(3) 0.14573(15) 0.10900(10) 0.0501(5) Uani 1 1 d . . . H1 H 0.4095 0.1454 0.1501 0.060 Uiso 1 1 calc R . . C2 C 0.3096(3) 0.05476(17) 0.08027(12) 0.0623(6) Uani 1 1 d . . . H2 H 0.3295 -0.0059 0.1019 0.075 Uiso 1 1 calc R . . C3 C 0.2340(3) 0.05543(16) 0.01926(12) 0.0631(6) Uani 1 1 d . . . H3 H 0.2043 -0.0051 -0.0013 0.076 Uiso 1 1 calc R . . C4 C 0.2025(3) 0.14608(16) -0.01134(11) 0.0528(5) Uani 1 1 d . . . H4 H 0.1509 0.1475 -0.0527 0.063 Uiso 1 1 calc R . . C5 C 0.2477(2) 0.23455(13) 0.01977(8) 0.0369(4) Uani 1 1 d . . . C6 C 0.2186(2) 0.33710(14) -0.00690(8) 0.0354(3) Uani 1 1 d . . . C7 C 0.1456(2) 0.36219(15) -0.06719(9) 0.0439(4) Uani 1 1 d . . . H7 H 0.1040 0.3123 -0.0955 0.053 Uiso 1 1 calc R . . C8 C 0.1365(2) 0.46276(16) -0.08400(9) 0.0476(5) Uani 1 1 d . . . H8 H 0.0875 0.4805 -0.1242 0.057 Uiso 1 1 calc R . . C9 C 0.1982(2) 0.53797(15) -0.04266(9) 0.0433(4) Uani 1 1 d . . . H9 H 0.1926 0.6057 -0.0545 0.052 Uiso 1 1 calc R . . C10 C 0.26895(19) 0.50873(13) 0.01737(8) 0.0340(3) Uani 1 1 d . . . C11 C 0.3462(2) 0.57584(13) 0.06829(8) 0.0363(4) Uani 1 1 d . . . C12 C 0.3611(2) 0.67912(14) 0.06312(10) 0.0454(4) Uani 1 1 d . . . H12 H 0.3174 0.7124 0.0264 0.054 Uiso 1 1 calc R . . C13 C 0.4424(3) 0.73271(15) 0.11359(11) 0.0523(5) Uani 1 1 d . . . H13 H 0.4553 0.8025 0.1109 0.063 Uiso 1 1 calc R . . C14 C 0.5036(3) 0.68227(16) 0.16753(10) 0.0530(5) Uani 1 1 d . . . H14 H 0.5589 0.7174 0.2017 0.064 Uiso 1 1 calc R . . C15 C 0.4824(3) 0.57880(16) 0.17064(9) 0.0481(4) Uani 1 1 d . . . H15 H 0.5222 0.5450 0.2076 0.058 Uiso 1 1 calc R . . N4 N 0.57155(18) 0.33773(13) 0.17876(7) 0.0421(3) Uani 1 1 d . . . N5 N 1.1497(2) 0.36397(13) 0.17647(8) 0.0462(4) Uani 1 1 d . . . N6 N 0.9109(2) 0.34409(17) 0.36153(8) 0.0632(5) Uani 1 1 d . . . C16 C 0.8747(2) 0.34376(13) 0.24032(8) 0.0339(3) Uani 1 1 d . . . C17 C 0.7067(2) 0.34045(13) 0.20750(8) 0.0328(3) Uani 1 1 d . . . C18 C 1.0265(2) 0.35370(13) 0.20528(8) 0.0344(4) Uani 1 1 d . . . C19 C 0.8931(2) 0.34390(15) 0.30727(9) 0.0408(4) Uani 1 1 d . . . C20 C 0.8525(3) 0.08492(15) 0.16995(10) 0.0492(5) Uani 1 1 d . . . C21 C 0.8403(3) 0.14895(16) 0.11742(10) 0.0496(5) Uani 1 1 d . . . C22 C 0.7262(3) 0.00690(17) 0.17547(10) 0.0541(5) Uani 1 1 d . . . C23 C 0.9939(3) 0.09590(16) 0.21694(12) 0.0621(6) Uani 1 1 d . . . N7 N 0.8280(3) 0.20238(17) 0.07373(9) 0.0694(5) Uani 1 1 d . . . N8 N 0.6223(3) -0.05608(18) 0.18018(11) 0.0820(7) Uani 1 1 d . . . N9 N 1.1077(4) 0.10540(18) 0.25518(14) 0.0973(9) 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 0.03109(11) 0.03954(14) 0.02904(12) 0.00076(8) -0.00462(8) 0.00035(7) N1 0.0361(7) 0.0403(8) 0.0359(8) 0.0007(6) -0.0044(6) 0.0016(6) N2 0.0295(6) 0.0383(8) 0.0297(7) 0.0002(6) -0.0011(5) 0.0015(5) N3 0.0365(7) 0.0404(8) 0.0360(8) -0.0042(6) -0.0007(6) -0.0002(6) C1 0.0567(11) 0.0433(11) 0.0484(11) 0.0071(8) -0.0117(9) 0.0007(8) C2 0.0688(13) 0.0419(12) 0.0738(16) 0.0080(10) -0.0143(11) 0.0028(10) C3 0.0671(13) 0.0410(11) 0.0782(16) -0.0114(11) -0.0186(12) -0.0010(10) C4 0.0547(11) 0.0502(12) 0.0510(12) -0.0083(9) -0.0155(9) 0.0008(9) C5 0.0318(7) 0.0426(10) 0.0354(9) -0.0027(7) -0.0044(6) 0.0019(7) C6 0.0298(7) 0.0432(9) 0.0326(8) -0.0018(7) -0.0026(6) 0.0019(7) C7 0.0420(9) 0.0550(12) 0.0335(9) -0.0038(8) -0.0068(7) 0.0031(8) C8 0.0486(10) 0.0591(13) 0.0338(10) 0.0081(9) -0.0070(7) 0.0068(9) C9 0.0433(9) 0.0470(11) 0.0395(10) 0.0091(8) 0.0015(7) 0.0062(8) C10 0.0292(7) 0.0403(9) 0.0326(8) 0.0030(7) 0.0031(6) 0.0020(6) C11 0.0297(7) 0.0417(10) 0.0378(9) -0.0003(7) 0.0051(6) 0.0018(6) C12 0.0422(9) 0.0408(10) 0.0533(11) 0.0022(9) 0.0046(8) 0.0032(8) C13 0.0463(10) 0.0372(10) 0.0740(14) -0.0097(10) 0.0083(9) 0.0003(8) C14 0.0491(10) 0.0512(12) 0.0582(12) -0.0204(10) -0.0001(9) -0.0004(9) C15 0.0492(10) 0.0531(12) 0.0413(10) -0.0094(9) -0.0038(8) -0.0003(9) N4 0.0317(7) 0.0589(10) 0.0350(8) 0.0006(7) -0.0044(6) 0.0041(6) N5 0.0340(7) 0.0630(11) 0.0414(9) -0.0022(7) 0.0021(6) -0.0046(7) N6 0.0536(10) 0.0962(15) 0.0383(10) 0.0077(9) -0.0081(8) -0.0105(9) C16 0.0277(7) 0.0401(9) 0.0333(8) 0.0029(7) -0.0025(6) -0.0010(6) C17 0.0320(8) 0.0358(8) 0.0306(8) 0.0019(7) 0.0016(6) 0.0014(6) C18 0.0316(8) 0.0360(9) 0.0347(9) -0.0001(7) -0.0056(6) -0.0009(6) C19 0.0302(8) 0.0510(11) 0.0405(10) 0.0058(8) -0.0045(7) -0.0056(7) C20 0.0569(11) 0.0375(10) 0.0512(11) 0.0012(9) -0.0128(9) 0.0023(8) C21 0.0528(10) 0.0429(11) 0.0524(12) -0.0063(9) -0.0017(9) 0.0061(8) C22 0.0621(12) 0.0467(12) 0.0511(12) 0.0032(9) -0.0151(9) 0.0031(10) C23 0.0725(14) 0.0389(11) 0.0715(15) 0.0102(10) -0.0220(12) -0.0016(10) N7 0.0819(13) 0.0676(13) 0.0582(12) 0.0134(10) 0.0003(10) 0.0064(10) N8 0.0862(14) 0.0712(14) 0.0845(16) 0.0175(12) -0.0269(12) -0.0222(12) N9 0.1020(18) 0.0721(15) 0.109(2) 0.0210(13) -0.0600(16) -0.0128(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 Cu1 N2 1.9422(13) . ? Cu1 N4 1.9662(14) . ? Cu1 N1 2.0258(15) . ? Cu1 N3 2.0339(15) . ? Cu1 N5 2.1235(15) 1_455 ? N1 C1 1.337(2) . ? N1 C5 1.354(2) . ? N2 C10 1.337(2) . ? N2 C6 1.341(2) . ? N3 C15 1.340(2) . ? N3 C11 1.361(2) . ? C1 C2 1.380(3) . ? C2 C3 1.369(3) . ? C3 C4 1.374(3) . ? C4 C5 1.372(3) . ? C5 C6 1.478(2) . ? C6 C7 1.389(2) . ? C7 C8 1.377(3) . ? C8 C9 1.381(3) . ? C9 C10 1.393(2) . ? C10 C11 1.480(2) . ? C11 C12 1.375(3) . ? C12 C13 1.384(3) . ? C13 C14 1.370(3) . ? C14 C15 1.380(3) . ? N4 C17 1.144(2) . ? N5 C18 1.142(2) . ? N5 Cu1 2.1235(15) 1_655 ? N6 C19 1.141(2) . ? C16 C17 1.394(2) . ? C16 C18 1.397(2) . ? C16 C19 1.407(2) . ? C20 C21 1.391(3) . ? C20 C23 1.407(3) . ? C20 C22 1.408(3) . ? C21 N7 1.159(3) . ? C22 N8 1.147(3) . ? C23 N9 1.140(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 N4 151.30(6) . . ? N2 Cu1 N1 79.92(6) . . ? N4 Cu1 N1 98.20(6) . . ? N2 Cu1 N3 79.78(6) . . ? N4 Cu1 N3 96.72(6) . . ? N1 Cu1 N3 158.84(6) . . ? N2 Cu1 N5 107.25(6) . 1_455 ? N4 Cu1 N5 101.45(6) . 1_455 ? N1 Cu1 N5 93.71(6) . 1_455 ? N3 Cu1 N5 97.94(6) . 1_455 ? C1 N1 C5 118.84(16) . . ? C1 N1 Cu1 126.26(13) . . ? C5 N1 Cu1 114.76(11) . . ? C10 N2 C6 122.81(14) . . ? C10 N2 Cu1 118.88(11) . . ? C6 N2 Cu1 118.31(12) . . ? C15 N3 C11 118.65(17) . . ? C15 N3 Cu1 126.85(13) . . ? C11 N3 Cu1 114.49(11) . . ? N1 C1 C2 122.08(19) . . ? C3 C2 C1 118.8(2) . . ? C2 C3 C4 119.6(2) . . ? C5 C4 C3 119.37(19) . . ? N1 C5 C4 121.33(17) . . ? N1 C5 C6 113.56(15) . . ? C4 C5 C6 125.11(16) . . ? N2 C6 C7 119.45(17) . . ? N2 C6 C5 113.26(14) . . ? C7 C6 C5 127.27(16) . . ? C8 C7 C6 118.40(17) . . ? C7 C8 C9 121.65(17) . . ? C8 C9 C10 117.62(17) . . ? N2 C10 C9 120.06(16) . . ? N2 C10 C11 113.18(14) . . ? C9 C10 C11 126.74(16) . . ? N3 C11 C12 121.76(16) . . ? N3 C11 C10 113.60(15) . . ? C12 C11 C10 124.63(16) . . ? C11 C12 C13 118.79(18) . . ? C14 C13 C12 119.57(19) . . ? C13 C14 C15 119.27(18) . . ? N3 C15 C14 121.95(19) . . ? C17 N4 Cu1 161.47(15) . . ? C18 N5 Cu1 175.27(15) . 1_655 ? C17 C16 C18 118.44(15) . . ? C17 C16 C19 121.57(14) . . ? C18 C16 C19 119.86(14) . . ? N4 C17 C16 177.79(17) . . ? N5 C18 C16 178.54(19) . . ? N6 C19 C16 178.92(18) . . ? C21 C20 C23 120.26(19) . . ? C21 C20 C22 120.10(18) . . ? C23 C20 C22 119.62(19) . . ? N7 C21 C20 179.2(2) . . ? N8 C22 C20 179.4(3) . . ? N9 C23 C20 179.5(3) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.26 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.261 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.046 # Attachment 'CUTPPZ_compound-5.cif' data_ull1339=ull1337 _database_code_depnum_ccdc_archive 'CCDC 666749' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H19 Cu2 N18 O1.50' _chemical_formula_weight 902.81 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8741(6) _cell_length_b 12.8989(7) _cell_length_c 16.0258(8) _cell_angle_alpha 80.965(6) _cell_angle_beta 88.684(6) _cell_angle_gamma 89.289(4) _cell_volume 2015.19(19) _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 sheet _exptl_crystal_colour braun _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 910 _exptl_absorpt_coefficient_mu 1.115 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mok\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18852 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0897 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 6.41 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8862 _reflns_number_gt 5267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0271P)^2^+1.8728P] 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 8862 _refine_ls_number_parameters 623 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1248 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 Cu1 Cu 0.83396(5) 0.48173(3) 0.73105(3) 0.03422(14) Uani 1 1 d . . . Cu2 Cu 0.53598(5) 0.93051(3) 0.76216(3) 0.03677(14) Uani 1 1 d . . . N1 N 0.8138(3) 0.5400(2) 0.60874(17) 0.0320(7) Uani 1 1 d . . . N2 N 0.8123(3) 0.4664(2) 0.85713(17) 0.0325(7) Uani 1 1 d . . . N4 N 0.5145(3) 0.8593(2) 0.88210(18) 0.0372(7) Uani 1 1 d . . . N3 N 0.6012(3) 0.9602(2) 0.64215(19) 0.0432(8) Uani 1 1 d . . . N5 N 0.7480(3) 0.61716(19) 0.74155(16) 0.0243(6) Uani 1 1 d . . . N6 N 0.6327(3) 0.79844(19) 0.75490(16) 0.0253(6) Uani 1 1 d . . . C1 C 0.8365(5) 0.4860(3) 0.5453(3) 0.0471(10) Uani 1 1 d . . . C2 C 0.7978(6) 0.5231(4) 0.4645(3) 0.0627(14) Uani 1 1 d . . . C3 C 0.7299(6) 0.6161(4) 0.4485(3) 0.0641(14) Uani 1 1 d . . . C4 C 0.7049(4) 0.6733(3) 0.5139(2) 0.0448(10) Uani 1 1 d . . . C5 C 0.7502(3) 0.6348(2) 0.5929(2) 0.0280(8) Uani 1 1 d . . . C6 C 0.7707(3) 0.5545(3) 0.8860(2) 0.0284(8) Uani 1 1 d . . . C7 C 0.7877(4) 0.5669(3) 0.9691(2) 0.0386(9) Uani 1 1 d . . . C8 C 0.8391(4) 0.4829(4) 1.0247(3) 0.0489(11) Uani 1 1 d . . . C9 C 0.8740(4) 0.3925(4) 0.9971(3) 0.0541(13) Uani 1 1 d . . . C10 C 0.8642(4) 0.3868(3) 0.9121(3) 0.0462(11) Uani 1 1 d . . . C11 C 0.6818(4) 0.8845(2) 0.6175(2) 0.0348(9) Uani 1 1 d . . . C12 C 0.7632(5) 0.9044(3) 0.5458(3) 0.0489(11) Uani 1 1 d . . . C13 C 0.7561(7) 1.0029(4) 0.4964(3) 0.0768(17) Uani 1 1 d . . . C14 C 0.6680(7) 1.0768(4) 0.5186(3) 0.0804(19) Uani 1 1 d . . . C15 C 0.5933(6) 1.0535(3) 0.5919(3) 0.0655(15) Uani 1 1 d . . . C16 C 0.4386(5) 0.8958(3) 0.9408(3) 0.0517(11) Uani 1 1 d . . . C17 C 0.4007(5) 0.8344(4) 1.0154(3) 0.0529(12) Uani 1 1 d . . . C18 C 0.4395(4) 0.7315(3) 1.0290(2) 0.0405(10) Uani 1 1 d . . . C19 C 0.5173(4) 0.6921(3) 0.9688(2) 0.0335(8) Uani 1 1 d . . . C20 C 0.5574(4) 0.7576(3) 0.8962(2) 0.0292(8) Uani 1 1 d . . . C21 C 0.7270(3) 0.6840(2) 0.6695(2) 0.0263(8) Uani 1 1 d . . . C22 C 0.6829(4) 0.7857(2) 0.6790(2) 0.0283(8) Uani 1 1 d . . . C23 C 0.6379(3) 0.7268(2) 0.82504(19) 0.0241(7) Uani 1 1 d . . . C24 C 0.7153(3) 0.6360(2) 0.8192(2) 0.0240(7) Uani 1 1 d . . . N32 N 0.8909(4) 0.3393(2) 0.7210(2) 0.0529(9) Uani 1 1 d . . . N33 N 1.2110(6) 0.1327(4) 0.6554(3) 0.0922(16) Uani 1 1 d . . . N34 N 0.8102(6) 0.0052(4) 0.7700(5) 0.146(3) Uani 1 1 d . . . C31 C 0.9722(6) 0.1536(3) 0.7154(3) 0.0628(13) Uani 1 1 d . . . C32 C 0.9272(4) 0.2558(3) 0.7186(3) 0.0492(11) Uani 1 1 d . . . C33 C 1.1034(7) 0.1399(4) 0.6819(4) 0.0697(16) Uani 1 1 d . . . C34 C 0.8841(6) 0.0705(4) 0.7450(4) 0.091(2) Uani 1 1 d . . . N36 N 1.0539(4) 0.5360(2) 0.74155(19) 0.0439(8) Uani 1 1 d . . . N37 N 1.4187(4) 0.6879(3) 0.6154(2) 0.0632(11) Uani 1 1 d . . . N38 N 1.4506(4) 0.5052(3) 0.8697(2) 0.0493(9) Uani 1 1 d . . . C35 C 1.3059(4) 0.5746(3) 0.7422(2) 0.0343(8) Uani 1 1 d . . . C36 C 1.1671(4) 0.5534(3) 0.7425(2) 0.0324(8) Uani 1 1 d . . . C37 C 1.3674(4) 0.6369(3) 0.6717(3) 0.0432(10) Uani 1 1 d . . . C38 C 1.3842(4) 0.5363(3) 0.8131(2) 0.0361(9) Uani 1 1 d . . . N40 N 0.4953(4) 1.0737(2) 0.7800(2) 0.0501(9) Uani 1 1 d . . . N42 N 0.5887(4) 1.4038(3) 0.7089(3) 0.0698(12) Uani 1 1 d . . . N41 N 0.2029(5) 1.3023(3) 0.8508(3) 0.0784(13) Uani 1 1 d . . . C39 C 0.4242(4) 1.2632(3) 0.7765(2) 0.0365(9) Uani 1 1 d . . . C40 C 0.4614(4) 1.1593(3) 0.7775(2) 0.0389(9) Uani 1 1 d . . . C41 C 0.3012(5) 1.2862(3) 0.8161(3) 0.0455(10) Uani 1 1 d . . . C42 C 0.5144(4) 1.3414(3) 0.7392(2) 0.0429(10) Uani 1 1 d . . . N44 N 0.3322(4) 0.8851(3) 0.7352(2) 0.0590(10) Uani 1 1 d . . . N46 N 0.0438(5) 0.7506(4) 0.5757(3) 0.0882(16) Uani 1 1 d . . . N45 N -0.0561(5) 0.7727(3) 0.8446(3) 0.0791(14) Uani 1 1 d . . . C43 C 0.1011(4) 0.8104(3) 0.7145(3) 0.0555(12) Uani 1 1 d . . . C44 C 0.2277(5) 0.8523(3) 0.7258(3) 0.0489(11) Uani 1 1 d . . . C45 C 0.0137(5) 0.7900(3) 0.7852(4) 0.0614(14) Uani 1 1 d . . . C46 C 0.0695(5) 0.7776(4) 0.6372(4) 0.0637(14) Uani 1 1 d . . . O1W O 0.9781(16) 0.1424(9) 0.9448(10) 0.202(6) Uani 0.50 1 d P . . O2W O 0.2056(11) 1.0695(10) 1.0266(8) 0.316(6) Uani 1 1 d . . . H1 H 0.884(4) 0.420(3) 0.557(2) 0.037(10) Uiso 1 1 d . . . H2 H 0.821(5) 0.481(4) 0.426(3) 0.075(15) Uiso 1 1 d . . . H3 H 0.698(5) 0.645(4) 0.396(3) 0.094(18) Uiso 1 1 d . . . H4 H 0.651(4) 0.733(3) 0.506(2) 0.052(12) Uiso 1 1 d . . . H7 H 0.762(3) 0.628(2) 0.9848(19) 0.020(9) Uiso 1 1 d . . . H8 H 0.856(4) 0.499(3) 1.077(2) 0.041(11) Uiso 1 1 d . . . H9 H 0.912(4) 0.337(3) 1.031(3) 0.070(14) Uiso 1 1 d . . . H10 H 0.891(4) 0.324(3) 0.887(2) 0.040(10) Uiso 1 1 d . . . H12 H 0.824(4) 0.857(3) 0.535(2) 0.039(11) Uiso 1 1 d . . . H13 H 0.810(4) 1.016(3) 0.451(3) 0.059(13) Uiso 1 1 d . . . H14 H 0.659(5) 1.136(4) 0.488(3) 0.073(14) Uiso 1 1 d . . . H15 H 0.537(4) 1.099(3) 0.615(2) 0.054(13) Uiso 1 1 d . . . H16 H 0.408(4) 0.961(3) 0.926(2) 0.045(11) Uiso 1 1 d . . . H17 H 0.349(4) 0.861(3) 1.050(2) 0.049(12) Uiso 1 1 d . . . H19 H 0.412(3) 0.687(3) 1.072(2) 0.031(10) Uiso 1 1 d . . . H18 H 0.545(3) 0.623(2) 0.9757(18) 0.020(8) 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 0.0391(3) 0.0226(2) 0.0397(3) -0.00249(18) 0.0053(2) 0.00601(19) Cu2 0.0439(3) 0.0222(2) 0.0437(3) -0.00452(19) 0.0024(2) 0.0072(2) N1 0.0332(19) 0.0314(15) 0.0331(16) -0.0111(13) 0.0065(13) -0.0019(13) N2 0.0275(18) 0.0258(14) 0.0403(17) 0.0059(13) 0.0034(13) 0.0014(12) N4 0.046(2) 0.0278(15) 0.0400(18) -0.0112(13) 0.0044(15) 0.0009(14) N3 0.055(2) 0.0253(15) 0.0458(19) 0.0044(14) 0.0010(16) 0.0081(15) N5 0.0223(16) 0.0220(13) 0.0282(15) -0.0027(11) 0.0006(12) -0.0002(11) N6 0.0265(17) 0.0226(13) 0.0272(15) -0.0048(11) -0.0012(12) -0.0019(12) C1 0.052(3) 0.044(2) 0.049(3) -0.020(2) 0.008(2) 0.001(2) C2 0.082(4) 0.070(3) 0.042(3) -0.030(3) 0.003(2) 0.005(3) C3 0.078(4) 0.081(4) 0.036(3) -0.017(2) -0.007(2) 0.002(3) C4 0.048(3) 0.052(3) 0.035(2) -0.0075(19) -0.0014(19) 0.005(2) C5 0.028(2) 0.0298(17) 0.0265(18) -0.0054(14) 0.0020(15) -0.0036(15) C6 0.0174(19) 0.0312(17) 0.0337(19) 0.0036(15) 0.0028(14) -0.0006(14) C7 0.029(2) 0.051(2) 0.033(2) 0.0009(19) 0.0024(17) 0.0047(19) C8 0.029(2) 0.077(3) 0.034(2) 0.011(2) 0.0013(18) 0.002(2) C9 0.039(3) 0.061(3) 0.051(3) 0.026(2) 0.002(2) 0.008(2) C10 0.037(3) 0.033(2) 0.060(3) 0.014(2) 0.005(2) 0.0046(18) C11 0.045(2) 0.0241(17) 0.033(2) 0.0024(15) -0.0006(17) 0.0010(16) C12 0.064(3) 0.037(2) 0.042(2) 0.0040(18) 0.011(2) 0.006(2) C13 0.123(5) 0.046(3) 0.050(3) 0.021(2) 0.026(3) 0.003(3) C14 0.139(6) 0.036(2) 0.055(3) 0.021(2) 0.017(3) 0.018(3) C15 0.109(5) 0.033(2) 0.051(3) 0.005(2) 0.006(3) 0.021(3) C16 0.066(3) 0.038(2) 0.052(3) -0.015(2) 0.007(2) 0.015(2) C17 0.056(3) 0.061(3) 0.045(3) -0.022(2) 0.014(2) 0.011(2) C18 0.039(3) 0.049(2) 0.033(2) -0.0073(19) 0.0071(18) -0.0053(19) C19 0.033(2) 0.0337(19) 0.035(2) -0.0056(16) -0.0036(16) -0.0006(17) C20 0.029(2) 0.0287(17) 0.0311(19) -0.0077(15) -0.0004(15) -0.0036(15) C21 0.023(2) 0.0267(16) 0.0284(18) -0.0023(14) -0.0021(14) -0.0016(14) C22 0.030(2) 0.0245(16) 0.0293(19) -0.0012(14) -0.0023(15) 0.0011(15) C23 0.0213(19) 0.0228(16) 0.0286(18) -0.0045(14) -0.0004(14) -0.0022(14) C24 0.0208(19) 0.0225(16) 0.0277(18) -0.0010(13) 0.0004(14) -0.0016(14) N32 0.052(2) 0.0284(17) 0.078(3) -0.0086(17) 0.0094(19) 0.0063(16) N33 0.106(5) 0.082(3) 0.090(4) -0.025(3) 0.000(3) 0.037(3) N34 0.096(5) 0.045(3) 0.293(8) -0.005(4) -0.060(5) -0.009(3) C31 0.072(4) 0.031(2) 0.088(3) -0.018(2) -0.020(3) 0.018(2) C32 0.050(3) 0.038(2) 0.062(3) -0.013(2) -0.007(2) 0.009(2) C33 0.089(5) 0.043(3) 0.080(4) -0.021(2) -0.015(3) 0.030(3) C34 0.068(4) 0.037(3) 0.171(6) -0.022(3) -0.048(4) 0.014(3) N36 0.037(2) 0.0469(19) 0.0443(19) 0.0039(15) 0.0014(16) -0.0048(16) N37 0.043(2) 0.069(3) 0.071(3) 0.010(2) 0.0108(19) -0.0066(19) N38 0.046(2) 0.055(2) 0.048(2) -0.0094(17) -0.0051(17) -0.0069(17) C35 0.024(2) 0.0373(19) 0.041(2) -0.0025(16) 0.0032(16) -0.0032(16) C36 0.042(3) 0.0307(18) 0.0244(18) -0.0038(14) 0.0035(17) -0.0008(17) C37 0.029(2) 0.045(2) 0.054(3) -0.003(2) 0.0004(19) -0.0033(18) C38 0.032(2) 0.0336(19) 0.044(2) -0.0124(17) 0.0078(18) -0.0078(17) N40 0.051(2) 0.0288(17) 0.071(2) -0.0102(16) 0.0060(18) 0.0030(16) N42 0.060(3) 0.045(2) 0.103(3) -0.013(2) 0.028(2) -0.008(2) N41 0.063(3) 0.054(2) 0.119(4) -0.020(2) 0.030(3) -0.001(2) C39 0.039(2) 0.0243(17) 0.047(2) -0.0093(16) -0.0012(18) 0.0033(16) C40 0.042(3) 0.0303(19) 0.045(2) -0.0079(17) 0.0008(18) -0.0003(18) C41 0.048(3) 0.0266(19) 0.061(3) -0.0065(18) 0.001(2) -0.0014(19) C42 0.047(3) 0.031(2) 0.053(2) -0.0126(18) 0.000(2) 0.0072(19) N44 0.043(3) 0.057(2) 0.079(3) -0.0152(19) -0.007(2) -0.0076(19) N46 0.073(3) 0.098(4) 0.086(3) 0.013(3) -0.030(3) -0.023(3) N45 0.057(3) 0.078(3) 0.096(3) 0.009(3) -0.007(3) -0.012(2) C43 0.037(3) 0.039(2) 0.085(4) 0.013(2) -0.010(2) -0.0092(19) C44 0.042(3) 0.031(2) 0.070(3) 0.0033(19) -0.006(2) 0.0013(19) C45 0.049(3) 0.041(2) 0.090(4) 0.008(3) -0.021(3) -0.005(2) C46 0.046(3) 0.055(3) 0.082(4) 0.018(3) -0.019(3) -0.013(2) O1W 0.221(15) 0.127(9) 0.253(15) -0.015(9) -0.009(11) 0.059(9) O2W 0.262(10) 0.359(13) 0.382(13) -0.221(11) -0.119(10) 0.114(9) _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 N32 1.944(3) . ? Cu1 N5 1.962(3) . ? Cu1 N1 2.000(3) . ? Cu1 N2 2.006(3) . ? Cu1 N36 2.308(4) . ? Cu2 N40 1.949(3) . ? Cu2 N6 1.961(3) . ? Cu2 N3 1.994(3) . ? Cu2 N4 2.004(3) . ? Cu2 N44 2.175(4) . ? N1 C1 1.334(5) . ? N1 C5 1.358(4) . ? N2 C10 1.348(4) . ? N2 C6 1.349(4) . ? N4 C16 1.329(5) . ? N4 C20 1.359(4) . ? N3 C15 1.342(5) . ? N3 C11 1.353(5) . ? N5 C24 1.337(4) . ? N5 C21 1.346(4) . ? N6 C22 1.337(4) . ? N6 C23 1.340(4) . ? C1 C2 1.369(6) . ? C2 C3 1.359(7) . ? C3 C4 1.390(6) . ? C4 C5 1.368(5) . ? C5 C21 1.481(5) . ? C6 C7 1.381(5) . ? C6 C24 1.486(4) . ? C7 C8 1.389(5) . ? C8 C9 1.349(7) . ? C9 C10 1.380(6) . ? C11 C12 1.379(5) . ? C11 C22 1.483(4) . ? C12 C13 1.390(6) . ? C13 C14 1.365(7) . ? C14 C15 1.367(7) . ? C16 C17 1.373(6) . ? C17 C18 1.363(6) . ? C18 C19 1.374(5) . ? C19 C20 1.380(5) . ? C20 C23 1.478(5) . ? C21 C22 1.407(4) . ? C23 C24 1.404(4) . ? N32 C32 1.136(5) . ? N33 C33 1.143(7) . ? N34 C34 1.139(7) . ? C31 C32 1.394(5) . ? C31 C34 1.406(8) . ? C31 C33 1.411(8) . ? N36 C36 1.144(4) . ? N37 C37 1.142(4) . ? N38 C38 1.148(4) . ? C35 C36 1.400(5) . ? C35 C37 1.409(5) . ? C35 C38 1.410(5) . ? N40 C40 1.145(4) . ? N42 C42 1.139(5) . ? N41 C41 1.141(5) . ? C39 C40 1.382(5) . ? C39 C42 1.405(5) . ? C39 C41 1.408(6) . ? N44 C44 1.142(5) . ? N46 C46 1.131(6) . ? N45 C45 1.157(6) . ? C43 C44 1.395(6) . ? C43 C45 1.401(8) . ? C43 C46 1.412(8) . ? 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 N32 Cu1 N5 171.17(13) . . ? N32 Cu1 N1 99.54(13) . . ? N5 Cu1 N1 80.32(11) . . ? N32 Cu1 N2 99.30(13) . . ? N5 Cu1 N2 80.02(11) . . ? N1 Cu1 N2 159.99(12) . . ? N32 Cu1 N36 92.69(14) . . ? N5 Cu1 N36 96.10(11) . . ? N1 Cu1 N36 96.37(11) . . ? N2 Cu1 N36 89.42(11) . . ? N40 Cu2 N6 162.12(13) . . ? N40 Cu2 N3 98.99(13) . . ? N6 Cu2 N3 80.57(12) . . ? N40 Cu2 N4 98.31(13) . . ? N6 Cu2 N4 80.07(12) . . ? N3 Cu2 N4 160.31(13) . . ? N40 Cu2 N44 98.15(14) . . ? N6 Cu2 N44 99.68(13) . . ? N3 Cu2 N44 96.19(14) . . ? N4 Cu2 N44 90.57(13) . . ? C1 N1 C5 119.0(3) . . ? C1 N1 Cu1 124.7(3) . . ? C5 N1 Cu1 115.2(2) . . ? C10 N2 C6 118.9(3) . . ? C10 N2 Cu1 124.8(3) . . ? C6 N2 Cu1 114.5(2) . . ? C16 N4 C20 119.1(3) . . ? C16 N4 Cu2 124.6(3) . . ? C20 N4 Cu2 114.7(2) . . ? C15 N3 C11 118.7(4) . . ? C15 N3 Cu2 125.4(3) . . ? C11 N3 Cu2 114.6(2) . . ? C24 N5 C21 125.2(3) . . ? C24 N5 Cu1 117.8(2) . . ? C21 N5 Cu1 117.1(2) . . ? C22 N6 C23 125.4(3) . . ? C22 N6 Cu2 116.9(2) . . ? C23 N6 Cu2 117.7(2) . . ? N1 C1 C2 122.1(4) . . ? C3 C2 C1 119.4(5) . . ? C2 C3 C4 119.3(5) . . ? C5 C4 C3 119.0(4) . . ? N1 C5 C4 121.0(3) . . ? N1 C5 C21 113.2(3) . . ? C4 C5 C21 125.5(3) . . ? N2 C6 C7 121.4(3) . . ? N2 C6 C24 113.6(3) . . ? C7 C6 C24 125.0(3) . . ? C6 C7 C8 118.4(4) . . ? C9 C8 C7 120.3(4) . . ? C8 C9 C10 119.0(4) . . ? N2 C10 C9 121.8(4) . . ? N3 C11 C12 121.2(3) . . ? N3 C11 C22 113.4(3) . . ? C12 C11 C22 125.1(4) . . ? C11 C12 C13 118.6(5) . . ? C14 C13 C12 119.9(5) . . ? C13 C14 C15 118.7(4) . . ? N3 C15 C14 122.7(5) . . ? N4 C16 C17 122.5(4) . . ? C18 C17 C16 118.9(4) . . ? C17 C18 C19 119.5(4) . . ? C18 C19 C20 119.7(4) . . ? N4 C20 C19 120.2(3) . . ? N4 C20 C23 113.5(3) . . ? C19 C20 C23 126.1(3) . . ? N5 C21 C22 116.1(3) . . ? N5 C21 C5 112.9(3) . . ? C22 C21 C5 131.0(3) . . ? N6 C22 C21 116.8(3) . . ? N6 C22 C11 112.6(3) . . ? C21 C22 C11 130.6(3) . . ? N6 C23 C24 116.3(3) . . ? N6 C23 C20 112.8(3) . . ? C24 C23 C20 130.9(3) . . ? N5 C24 C23 116.9(3) . . ? N5 C24 C6 112.1(3) . . ? C23 C24 C6 130.9(3) . . ? C32 N32 Cu1 176.8(4) . . ? C32 C31 C34 118.3(5) . . ? C32 C31 C33 117.9(4) . . ? C34 C31 C33 123.8(4) . . ? N32 C32 C31 179.8(6) . . ? N33 C33 C31 177.2(6) . . ? N34 C34 C31 177.9(7) . . ? C36 N36 Cu1 172.2(3) . . ? C36 C35 C37 120.1(3) . . ? C36 C35 C38 120.3(3) . . ? C37 C35 C38 119.6(3) . . ? N36 C36 C35 179.0(4) . . ? N37 C37 C35 178.9(5) . . ? N38 C38 C35 178.4(4) . . ? C40 N40 Cu2 168.5(3) . . ? C40 C39 C42 118.3(4) . . ? C40 C39 C41 118.9(3) . . ? C42 C39 C41 122.8(3) . . ? N40 C40 C39 177.9(4) . . ? N41 C41 C39 177.4(5) . . ? N42 C42 C39 179.1(4) . . ? C44 N44 Cu2 173.4(3) . . ? C44 C43 C45 117.6(4) . . ? C44 C43 C46 120.7(4) . . ? C45 C43 C46 121.2(4) . . ? N44 C44 C43 179.0(4) . . ? N45 C45 C43 178.6(5) . . ? N46 C46 C43 179.4(5) . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.336 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.070