# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110503f-new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C84 H69 Cl6 Cu6 N21' _chemical_formula_weight 1966.54 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 29.024(3) _cell_length_b 29.024(3) _cell_length_c 11.2581(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8213.3(13) _cell_formula_units_Z 3 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2488 _cell_measurement_theta_min 2.427 _cell_measurement_theta_max 26.063 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2988 _exptl_absorpt_coefficient_mu 1.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6901 _exptl_absorpt_correction_T_max 0.8248 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 '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 10838 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3224 _reflns_number_gt 2121 _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^)+(0.1096P)^2^+22.0902P] 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 3224 _refine_ls_number_parameters 225 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0980 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.2003 _refine_ls_wR_factor_gt 0.1680 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.059 _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 0.73341(3) 0.86669(3) 0.33094(6) 0.0489(3) Uani 1 1 d . . . Cl1 Cl 0.75021(9) 0.87506(7) 0.53310(13) 0.0636(5) Uani 1 1 d . . . N1 N 0.73402(18) 0.93017(17) 0.2750(4) 0.0399(11) Uani 1 1 d . . . N2 N 0.73413(19) 0.80389(18) 0.2747(4) 0.0416(11) Uani 1 1 d . . . N3 N 0.73630(16) 1.06959(16) 0.1666(4) 0.0341(10) Uani 1 1 d . . . N4 N 0.8254(16) 0.8233(15) -0.010(3) 0.082(8) Uani 0.191(9) 1 d P A 1 N5 N 0.873(3) 0.898(3) 0.204(7) 0.082(8) Uani 0.088(8) 1 d P B 2 N6 N 0.9269(18) 0.8514(17) 0.181(4) 0.082(8) Uani 0.142(8) 1 d P C 3 N7 N 0.808(4) 0.906(4) 0.115(9) 0.082(8) Uani 0.079(10) 1 d P D 4 C1 C 0.7687(2) 0.9781(2) 0.3208(5) 0.0407(13) Uani 1 1 d . . . H1 H 0.7923 0.9798 0.3789 0.049 Uiso 1 1 calc R . . C2 C 0.7712(2) 1.0245(2) 0.2866(4) 0.0346(12) Uani 1 1 d . . . H2 H 0.7965 1.0568 0.3193 0.041 Uiso 1 1 calc R . . C3 C 0.73569(19) 1.02277(19) 0.2027(4) 0.0319(11) Uani 1 1 d . . . C4 C 0.7001(2) 0.9740(2) 0.1553(5) 0.0393(13) Uani 1 1 d . . . H4 H 0.6757 0.9714 0.0983 0.047 Uiso 1 1 calc R . . C5 C 0.7007(2) 0.9293(2) 0.1924(5) 0.0422(13) Uani 1 1 d . . . H5 H 0.6766 0.8969 0.1583 0.051 Uiso 1 1 calc R . . C6 C 0.7008(2) 0.7716(2) 0.1922(5) 0.0428(14) Uani 1 1 d . . . H6 H 0.6767 0.7800 0.1582 0.051 Uiso 1 1 calc R . . C7 C 0.6408(2) 1.0337(2) 0.1784(5) 0.0408(13) Uani 1 1 d . . . H7 H 0.6381 1.0094 0.2357 0.049 Uiso 1 1 calc R . . C8 C 0.68958(19) 1.06913(19) 0.1311(4) 0.0308(11) Uani 1 1 d . . . C9 C 0.6913(2) 1.1046(2) 0.0464(5) 0.0351(12) Uani 1 1 d . . . H9 H 0.7235 1.1297 0.0132 0.042 Uiso 1 1 calc R . . C10 C 0.7686(2) 0.7903(2) 0.3206(5) 0.0405(13) Uani 1 1 d . . . H10 H 0.7921 0.8122 0.3789 0.049 Uiso 1 1 calc R . . C11 C 0.78570(19) 1.11893(19) 0.1667(4) 0.0325(12) Uani 1 1 d . . . C12 C 0.8290(2) 1.1227(2) 0.1091(5) 0.0348(12) Uani 1 1 d . . . H12 H 0.8263 1.0934 0.0695 0.042 Uiso 1 1 calc R . . C13 C 0.8771(2) 1.1707(2) 0.1097(5) 0.0362(12) Uani 1 1 d . . . H13 H 0.9067 1.1732 0.0715 0.043 Uiso 1 1 calc R . . C14 C 0.8302(18) 0.8620(19) 0.028(4) 0.083(10) Uani 0.191(9) 1 d P A 1 C15 C 0.832(2) 0.9130(19) 0.062(5) 0.092(11) Uani 0.191(9) 1 d P A 1 H15A H 0.8566 0.9411 0.0112 0.138 Uiso 0.191(9) 1 calc PR A 1 H15B H 0.8437 0.9216 0.1432 0.138 Uiso 0.191(9) 1 calc PR A 1 H15C H 0.7974 0.9089 0.0541 0.138 Uiso 0.191(9) 1 calc PR A 1 C16 C 0.869(4) 0.937(5) 0.202(11) 0.083(10) Uani 0.088(8) 1 d P B 2 C17 C 0.871(4) 0.988(4) 0.164(9) 0.092(11) Uani 0.088(8) 1 d P B 2 H17A H 0.8572 0.9837 0.0850 0.110 Uiso 0.088(8) 1 calc PR B 2 H17B H 0.9072 1.0163 0.1661 0.110 Uiso 0.088(8) 1 calc PR B 2 H17C H 0.8499 0.9954 0.2175 0.110 Uiso 0.088(8) 1 calc PR B 2 C18 C 0.898(2) 0.844(2) 0.103(6) 0.083(10) Uani 0.142(8) 1 d P C 3 C19 C 0.859(3) 0.838(3) 0.008(6) 0.092(11) Uani 0.142(8) 1 d P C 3 H19A H 0.8704 0.8324 -0.0672 0.138 Uiso 0.142(8) 1 calc PR C 3 H19B H 0.8556 0.8693 0.0053 0.138 Uiso 0.142(8) 1 calc PR C 3 H19C H 0.8245 0.8077 0.0270 0.138 Uiso 0.142(8) 1 calc PR C 3 C20 C 0.850(5) 0.925(5) 0.164(12) 0.083(10) Uani 0.079(10) 1 d P D 4 C21 C 0.889(5) 0.944(4) 0.262(11) 0.092(11) Uani 0.079(10) 1 d P D 4 H21A H 0.9230 0.9494 0.2327 0.110 Uiso 0.079(10) 1 calc PR D 4 H21B H 0.8770 0.9173 0.3236 0.110 Uiso 0.079(10) 1 calc PR D 4 H21C H 0.8938 0.9764 0.2934 0.110 Uiso 0.079(10) 1 calc PR D 4 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 0.0677(6) 0.0343(5) 0.0559(5) 0.0014(3) 0.0038(4) 0.0338(4) Cl1 0.1128(15) 0.0542(10) 0.0433(9) -0.0052(7) -0.0107(9) 0.0564(10) N1 0.048(3) 0.034(3) 0.042(2) -0.001(2) -0.002(2) 0.023(2) N2 0.055(3) 0.035(3) 0.044(3) -0.002(2) -0.003(2) 0.029(2) N3 0.022(2) 0.025(2) 0.054(3) 0.0084(19) -0.0050(19) 0.0103(18) N4 0.067(17) 0.062(17) 0.086(18) 0.005(13) -0.011(14) 0.009(14) N5 0.067(17) 0.062(17) 0.086(18) 0.005(13) -0.011(14) 0.009(14) N6 0.067(17) 0.062(17) 0.086(18) 0.005(13) -0.011(14) 0.009(14) N7 0.067(17) 0.062(17) 0.086(18) 0.005(13) -0.011(14) 0.009(14) C1 0.045(3) 0.036(3) 0.044(3) -0.001(2) -0.009(3) 0.022(3) C2 0.035(3) 0.026(3) 0.043(3) -0.002(2) -0.007(2) 0.016(2) C3 0.031(3) 0.023(3) 0.038(3) 0.003(2) -0.002(2) 0.011(2) C4 0.042(3) 0.028(3) 0.041(3) 0.000(2) -0.011(2) 0.013(3) C5 0.047(3) 0.028(3) 0.042(3) -0.004(2) -0.006(3) 0.013(3) C6 0.051(4) 0.051(4) 0.041(3) -0.004(3) -0.006(3) 0.037(3) C7 0.033(3) 0.043(3) 0.039(3) 0.012(2) 0.001(2) 0.014(3) C8 0.024(3) 0.029(3) 0.036(3) 0.002(2) -0.004(2) 0.011(2) C9 0.026(3) 0.032(3) 0.045(3) 0.007(2) 0.004(2) 0.013(2) C10 0.046(3) 0.035(3) 0.043(3) -0.008(2) -0.009(3) 0.023(3) C11 0.023(3) 0.025(3) 0.044(3) 0.003(2) -0.007(2) 0.008(2) C12 0.030(3) 0.025(3) 0.047(3) -0.004(2) -0.005(2) 0.012(2) C13 0.027(3) 0.032(3) 0.049(3) 0.006(2) 0.003(2) 0.014(2) C14 0.07(2) 0.07(2) 0.08(2) 0.002(17) -0.003(17) 0.011(17) C15 0.07(2) 0.07(2) 0.09(3) 0.005(18) -0.003(19) 0.007(19) C16 0.07(2) 0.07(2) 0.08(2) 0.002(17) -0.003(17) 0.011(17) C17 0.07(2) 0.07(2) 0.09(3) 0.005(18) -0.003(19) 0.007(19) C18 0.07(2) 0.07(2) 0.08(2) 0.002(17) -0.003(17) 0.011(17) C19 0.07(2) 0.07(2) 0.09(3) 0.005(18) -0.003(19) 0.007(19) C20 0.07(2) 0.07(2) 0.08(2) 0.002(17) -0.003(17) 0.011(17) C21 0.07(2) 0.07(2) 0.09(3) 0.005(18) -0.003(19) 0.007(19) _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 N1 1.939(4) . ? Cu1 N2 1.939(4) . ? Cu1 Cl1 2.3147(17) . ? N1 C5 1.334(7) . ? N1 C1 1.348(7) . ? N2 C6 1.332(7) . ? N2 C10 1.348(7) . ? N3 C8 1.407(6) . ? N3 C3 1.410(6) . ? N3 C11 1.433(6) . ? N4 C14 1.15(6) . ? N5 C16 1.19(14) . ? N6 C18 1.15(7) . ? N7 C20 1.20(16) . ? C1 C2 1.366(7) . ? C1 H1 0.9300 . ? C2 C3 1.381(7) . ? C2 H2 0.9300 . ? C3 C4 1.375(7) . ? C4 C5 1.371(7) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.374(7) 14_455 ? C6 H6 0.9300 . ? C7 C6 1.374(7) 15 ? C7 C8 1.375(7) . ? C7 H7 0.9300 . ? C8 C9 1.385(7) . ? C9 C10 1.362(7) 15 ? C9 H9 0.9300 . ? C10 C9 1.361(7) 14_455 ? C10 H10 0.9300 . ? C11 C12 1.368(7) . ? C11 C13 1.375(7) 13_675 ? C12 C13 1.396(7) . ? C12 H12 0.9300 . ? C13 C11 1.375(7) 13_675 ? C13 H13 0.9300 . ? C14 C15 1.50(7) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.51(16) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.51(9) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.47(16) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 N1 Cu1 N2 142.00(19) . . ? N1 Cu1 Cl1 108.55(14) . . ? N2 Cu1 Cl1 108.58(14) . . ? C5 N1 C1 116.5(5) . . ? C5 N1 Cu1 123.2(4) . . ? C1 N1 Cu1 120.3(4) . . ? C6 N2 C10 116.5(4) . . ? C6 N2 Cu1 123.0(4) . . ? C10 N2 Cu1 120.5(4) . . ? C8 N3 C3 121.7(4) . . ? C8 N3 C11 119.2(4) . . ? C3 N3 C11 119.2(4) . . ? N1 C1 C2 123.6(5) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C1 C2 C3 119.1(5) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 117.8(5) . . ? C4 C3 N3 121.4(4) . . ? C2 C3 N3 120.9(4) . . ? C5 C4 C3 119.8(5) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 123.2(5) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? N2 C6 C7 122.9(5) . 14_455 ? N2 C6 H6 118.6 . . ? C7 C6 H6 118.6 14_455 . ? C6 C7 C8 120.1(5) 15 . ? C6 C7 H7 119.9 15 . ? C8 C7 H7 119.9 . . ? C7 C8 C9 117.5(5) . . ? C7 C8 N3 121.6(4) . . ? C9 C8 N3 120.8(4) . . ? C10 C9 C8 118.9(5) 15 . ? C10 C9 H9 120.5 15 . ? C8 C9 H9 120.5 . . ? N2 C10 C9 124.1(5) . 14_455 ? N2 C10 H10 118.0 . . ? C9 C10 H10 118.0 14_455 . ? C12 C11 C13 119.9(5) . 13_675 ? C12 C11 N3 120.0(5) . . ? C13 C11 N3 120.1(5) 13_675 . ? C11 C12 C13 120.0(5) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C11 C13 C12 120.0(5) 13_675 . ? C11 C13 H13 120.0 13_675 . ? C12 C13 H13 120.0 . . ? N4 C14 C15 172(5) . . ? N5 C16 C17 163(10) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N6 C18 C19 174(8) . . ? N7 C20 C21 159(10) . . ? 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 C5 50.6(6) . . . . ? Cl1 Cu1 N1 C5 -142.1(4) . . . . ? N2 Cu1 N1 C1 -130.4(4) . . . . ? Cl1 Cu1 N1 C1 36.9(4) . . . . ? N1 Cu1 N2 C6 -50.6(6) . . . . ? Cl1 Cu1 N2 C6 142.1(4) . . . . ? N1 Cu1 N2 C10 130.7(4) . . . . ? Cl1 Cu1 N2 C10 -36.6(5) . . . . ? C5 N1 C1 C2 -0.4(8) . . . . ? Cu1 N1 C1 C2 -179.5(4) . . . . ? N1 C1 C2 C3 1.7(9) . . . . ? C1 C2 C3 C4 -1.6(8) . . . . ? C1 C2 C3 N3 178.8(5) . . . . ? C8 N3 C3 C4 31.8(7) . . . . ? C11 N3 C3 C4 -148.6(5) . . . . ? C8 N3 C3 C2 -148.7(5) . . . . ? C11 N3 C3 C2 31.0(7) . . . . ? C2 C3 C4 C5 0.4(8) . . . . ? N3 C3 C4 C5 179.9(5) . . . . ? C1 N1 C5 C4 -1.0(8) . . . . ? Cu1 N1 C5 C4 178.1(4) . . . . ? C3 C4 C5 N1 1.0(9) . . . . ? C10 N2 C6 C7 0.6(8) . . . 14_455 ? Cu1 N2 C6 C7 -178.1(4) . . . 14_455 ? C6 C7 C8 C9 0.3(8) 15 . . . ? C6 C7 C8 N3 -179.6(5) 15 . . . ? C3 N3 C8 C7 31.3(7) . . . . ? C11 N3 C8 C7 -148.4(5) . . . . ? C3 N3 C8 C9 -148.6(5) . . . . ? C11 N3 C8 C9 31.7(7) . . . . ? C7 C8 C9 C10 -1.3(8) . . . 15 ? N3 C8 C9 C10 178.6(5) . . . 15 ? C6 N2 C10 C9 0.5(8) . . . 14_455 ? Cu1 N2 C10 C9 179.3(4) . . . 14_455 ? C8 N3 C11 C12 -127.8(5) . . . . ? C3 N3 C11 C12 52.5(7) . . . . ? C8 N3 C11 C13 51.6(7) . . . 13_675 ? C3 N3 C11 C13 -128.1(5) . . . 13_675 ? C13 C11 C12 C13 1.0(8) 13_675 . . . ? N3 C11 C12 C13 -179.7(4) . . . . ? C11 C12 C13 C11 -1.0(8) . . . 13_675 ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 0.000 53.4 -1.5 2 0.000 0.000 0.500 204.2 8.2 3 0.333 0.667 0.167 205.3 8.0 4 0.333 0.667 0.667 52.9 -1.4 5 0.667 0.333 0.833 205.4 8.1 6 0.667 0.333 0.333 52.9 -1.4 _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.652 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 939480' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110503e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H32 Cl2 Cu2 N6 O2 S2' _chemical_formula_weight 770.72 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 10.7383(12) _cell_length_b 15.1497(16) _cell_length_c 10.7339(11) _cell_angle_alpha 90.00 _cell_angle_beta 117.9710(10) _cell_angle_gamma 90.00 _cell_volume 1542.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1500 _cell_measurement_theta_min 2.534 _cell_measurement_theta_max 26.349 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 1.728 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7023 _exptl_absorpt_correction_T_max 0.8194 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 '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 3863 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1415 _reflns_number_gt 1046 _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^)+(0.1141P)^2^+12.2392P] 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 1415 _refine_ls_number_parameters 107 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.2086 _refine_ls_wR_factor_gt 0.1834 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.5000 0.60115(8) 0.5000 0.0426(5) Uani 1 2 d S . . Cl1 Cl 0.6972(2) 0.5000 0.6057(2) 0.0383(6) Uani 1 2 d S . . N1 N 0.5094(6) 0.6757(3) 0.6629(5) 0.0329(12) Uani 1 1 d . . . N2 N 0.5000 0.8133(5) 1.0000 0.0320(17) Uani 1 2 d S . . S1 S 0.6778(4) 0.5000 0.2496(4) 0.0763(11) Uani 1 2 d S . . O1 O 0.6581(13) 0.5000 0.1007(12) 0.100(4) Uani 1 2 d S . . C1 C 0.4376(7) 0.7508(4) 0.6426(6) 0.0358(15) Uani 1 1 d . . . H1 H 0.3888 0.7722 0.5509 0.043 Uiso 1 1 calc R . . C2 C 0.4307(7) 0.7989(4) 0.7483(6) 0.0353(15) Uani 1 1 d . . . H2 H 0.3794 0.8511 0.7283 0.042 Uiso 1 1 calc R . . C3 C 0.5029(7) 0.7669(4) 0.8865(6) 0.0279(13) Uani 1 1 d . . . C4 C 0.5771(7) 0.6894(4) 0.9087(6) 0.0328(14) Uani 1 1 d . . . H4 H 0.6257 0.6660 0.9991 0.039 Uiso 1 1 calc R . . C5 C 0.5792(7) 0.6466(4) 0.7969(6) 0.0357(15) Uani 1 1 d . . . H5 H 0.6316 0.5950 0.8146 0.043 Uiso 1 1 calc R . . C6 C 0.5000 0.9080(5) 1.0000 0.0263(18) Uani 1 2 d S . . C7 C 0.5861(6) 0.9541(4) 0.9585(6) 0.0303(13) Uani 1 1 d . . . H7 H 0.6440 0.9236 0.9306 0.036 Uiso 1 1 calc R . . C8 C 0.7975(12) 0.5851(7) 0.3396(12) 0.085(3) Uani 1 1 d . . . H8A H 0.8833 0.5757 0.3342 0.127 Uiso 1 1 calc R . . H8B H 0.8175 0.5854 0.4366 0.127 Uiso 1 1 calc R . . H8C H 0.7572 0.6408 0.2971 0.127 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 0.0722(9) 0.0322(7) 0.0284(6) 0.000 0.0277(6) 0.000 Cl1 0.0431(13) 0.0270(11) 0.0419(13) 0.000 0.0174(10) 0.000 N1 0.049(3) 0.028(3) 0.026(3) 0.003(2) 0.021(2) 0.003(2) N2 0.061(5) 0.018(3) 0.027(4) 0.000 0.029(4) 0.000 S1 0.092(3) 0.065(2) 0.084(3) 0.000 0.052(2) 0.000 O1 0.122(9) 0.111(9) 0.080(7) 0.000 0.059(7) 0.000 C1 0.057(4) 0.028(3) 0.022(3) 0.004(2) 0.019(3) 0.004(3) C2 0.051(4) 0.023(3) 0.030(3) 0.002(2) 0.018(3) 0.005(3) C3 0.046(4) 0.019(3) 0.024(3) -0.003(2) 0.022(3) -0.001(3) C4 0.049(4) 0.031(3) 0.021(3) 0.005(2) 0.018(3) 0.007(3) C5 0.050(4) 0.029(3) 0.030(3) 0.001(3) 0.019(3) 0.009(3) C6 0.043(5) 0.014(4) 0.024(4) 0.000 0.018(4) 0.000 C7 0.043(3) 0.026(3) 0.028(3) -0.001(2) 0.022(3) 0.000(3) C8 0.096(8) 0.084(7) 0.077(7) -0.013(6) 0.042(6) 0.002(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 N1 2.045(5) . ? Cu1 N1 2.045(5) 2_656 ? Cu1 Cl1 2.4219(19) 5_666 ? Cu1 Cl1 2.4219(19) . ? Cl1 Cu1 2.4219(19) 5_666 ? N1 C1 1.333(8) . ? N1 C5 1.346(8) . ? N2 C3 1.419(6) . ? N2 C3 1.419(6) 2_657 ? N2 C6 1.434(10) . ? S1 O1 1.511(11) . ? S1 C8 1.756(11) . ? S1 C8 1.756(11) 6_565 ? C1 C2 1.379(9) . ? C1 H1 0.9300 . ? C2 C3 1.398(8) . ? C2 H2 0.9300 . ? C3 C4 1.377(9) . ? C4 C5 1.373(8) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.389(7) . ? C6 C7 1.389(7) 2_657 ? C7 C7 1.389(12) 6_575 ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 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 N1 Cu1 N1 112.9(3) . 2_656 ? N1 Cu1 Cl1 115.59(16) . 5_666 ? N1 Cu1 Cl1 105.51(15) 2_656 5_666 ? N1 Cu1 Cl1 105.51(15) . . ? N1 Cu1 Cl1 115.59(16) 2_656 . ? Cl1 Cu1 Cl1 101.49(8) 5_666 . ? Cu1 Cl1 Cu1 78.51(8) 5_666 . ? C1 N1 C5 116.3(5) . . ? C1 N1 Cu1 122.6(4) . . ? C5 N1 Cu1 120.8(4) . . ? C3 N2 C3 120.7(7) . 2_657 ? C3 N2 C6 119.7(3) . . ? C3 N2 C6 119.7(3) 2_657 . ? O1 S1 C8 106.5(5) . . ? O1 S1 C8 106.5(5) . 6_565 ? C8 S1 C8 94.5(8) . 6_565 ? N1 C1 C2 124.5(6) . . ? N1 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C1 C2 C3 118.2(6) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C4 C3 C2 117.8(5) . . ? C4 C3 N2 121.2(5) . . ? C2 C3 N2 121.0(5) . . ? C5 C4 C3 119.8(6) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 123.4(6) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C7 C6 C7 119.5(8) . 2_657 ? C7 C6 N2 120.2(4) . . ? C7 C6 N2 120.2(4) 2_657 . ? C7 C7 C6 120.2(4) 6_575 . ? C7 C7 H7 119.9 6_575 . ? C6 C7 H7 119.9 . . ? S1 C8 H8A 109.5 . . ? S1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 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 N1 Cu1 Cl1 Cu1 120.92(16) . . . 5_666 ? N1 Cu1 Cl1 Cu1 -113.57(17) 2_656 . . 5_666 ? Cl1 Cu1 Cl1 Cu1 0.0 5_666 . . 5_666 ? N1 Cu1 N1 C1 37.7(5) 2_656 . . . ? Cl1 Cu1 N1 C1 -83.9(5) 5_666 . . . ? Cl1 Cu1 N1 C1 164.9(5) . . . . ? N1 Cu1 N1 C5 -148.5(6) 2_656 . . . ? Cl1 Cu1 N1 C5 89.9(5) 5_666 . . . ? Cl1 Cu1 N1 C5 -21.3(5) . . . . ? C5 N1 C1 C2 -0.2(10) . . . . ? Cu1 N1 C1 C2 173.8(5) . . . . ? N1 C1 C2 C3 -0.4(10) . . . . ? C1 C2 C3 C4 0.2(9) . . . . ? C1 C2 C3 N2 180.0(6) . . . . ? C3 N2 C3 C4 -36.5(5) 2_657 . . . ? C6 N2 C3 C4 143.5(5) . . . . ? C3 N2 C3 C2 143.7(7) 2_657 . . . ? C6 N2 C3 C2 -36.3(7) . . . . ? C2 C3 C4 C5 0.5(10) . . . . ? N2 C3 C4 C5 -179.2(6) . . . . ? C1 N1 C5 C4 1.0(10) . . . . ? Cu1 N1 C5 C4 -173.1(5) . . . . ? C3 C4 C5 N1 -1.2(11) . . . . ? C3 N2 C6 C7 -41.6(4) . . . . ? C3 N2 C6 C7 138.4(4) 2_657 . . . ? C3 N2 C6 C7 138.4(4) . . . 2_657 ? C3 N2 C6 C7 -41.6(4) 2_657 . . 2_657 ? C7 C6 C7 C7 0.000(3) 2_657 . . 6_575 ? N2 C6 C7 C7 180.000(3) . . . 6_575 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.677 _refine_diff_density_min -1.533 _refine_diff_density_rms 0.146 _database_code_depnum_ccdc_archive 'CCDC 939481' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110404a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 Cu1 I1 N6' _chemical_formula_weight 606.92 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' I I -0.4742 1.8119 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6592(10) _cell_length_b 14.6130(17) _cell_length_c 20.536(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.1880(10) _cell_angle_gamma 90.00 _cell_volume 2294.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3873 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 25.654 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 2.325 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6053 _exptl_absorpt_correction_T_max 0.8008 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 '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 11880 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0429 _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 -24 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4049 _reflns_number_gt 3030 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0309P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4049 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.20879(6) 0.59863(3) 0.24139(2) 0.03850(14) Uani 1 1 d . . . I1 I 0.00585(4) 0.48840(2) 0.176317(15) 0.06102(12) Uani 1 1 d . . . N1 N 0.8595(3) 0.41306(17) 0.38567(13) 0.0332(7) Uani 1 1 d . . . N2 N 0.3582(4) 0.69213(18) 0.18975(14) 0.0342(7) Uani 1 1 d . . . N3 N 0.3989(4) 0.52581(17) 0.29650(14) 0.0347(7) Uani 1 1 d . . . N4 N -0.1644(4) 0.84447(17) 0.44249(14) 0.0344(7) Uani 1 1 d . . . N5 N 0.0799(4) 0.69288(18) 0.29838(14) 0.0343(7) Uani 1 1 d . . . N6 N -0.6038(4) 0.7453(2) 0.53603(18) 0.0612(10) Uani 1 1 d . . . C1 C 0.9324(4) 0.4571(2) 0.44379(16) 0.0284(8) Uani 1 1 d . . . C2 C 0.9198(4) 0.4153(2) 0.50341(17) 0.0340(8) Uani 1 1 d . . . H2 H 0.8664 0.3583 0.5058 0.041 Uiso 1 1 calc R . . C3 C 0.9863(4) 0.4578(2) 0.55992(17) 0.0346(8) Uani 1 1 d . . . H3 H 0.9767 0.4296 0.6002 0.042 Uiso 1 1 calc R . . C4 C 0.2790(4) 0.7669(2) 0.16437(19) 0.0444(10) Uani 1 1 d . . . H4 H 0.1577 0.7696 0.1638 0.053 Uiso 1 1 calc R . . C5 C 0.3663(5) 0.8397(2) 0.13913(19) 0.0432(10) Uani 1 1 d . . . H5 H 0.3045 0.8899 0.1222 0.052 Uiso 1 1 calc R . . C6 C 0.5471(4) 0.8376(2) 0.13910(16) 0.0303(8) Uani 1 1 d . . . C7 C 0.6304(4) 0.7595(2) 0.16293(17) 0.0335(8) Uani 1 1 d . . . H7 H 0.7513 0.7540 0.1625 0.040 Uiso 1 1 calc R . . C8 C 0.5312(4) 0.6898(2) 0.18744(16) 0.0331(8) Uani 1 1 d . . . H8 H 0.5893 0.6379 0.2034 0.040 Uiso 1 1 calc R . . C9 C 0.4952(5) 0.4637(2) 0.26637(18) 0.0375(9) Uani 1 1 d . . . H9 H 0.4574 0.4462 0.2244 0.045 Uiso 1 1 calc R . . C10 C 0.6443(4) 0.4245(2) 0.29269(17) 0.0357(8) Uani 1 1 d . . . H10 H 0.7060 0.3830 0.2684 0.043 Uiso 1 1 calc R . . C11 C 0.7042(4) 0.4465(2) 0.35608(17) 0.0291(8) Uani 1 1 d . . . C12 C 0.6018(4) 0.5092(2) 0.38894(17) 0.0335(8) Uani 1 1 d . . . H12 H 0.6323 0.5256 0.4318 0.040 Uiso 1 1 calc R . . C13 C 0.4559(4) 0.5459(2) 0.35700(18) 0.0345(8) Uani 1 1 d . . . H13 H 0.3919 0.5884 0.3796 0.041 Uiso 1 1 calc R . . C14 C -0.0809(4) 0.9239(2) 0.47158(17) 0.0319(8) Uani 1 1 d . . . C15 C -0.0442(5) 0.9991(2) 0.43347(18) 0.0390(9) Uani 1 1 d . . . H15 H -0.0733 0.9987 0.3889 0.047 Uiso 1 1 calc R . . C16 C 0.0362(5) 1.0748(2) 0.46254(18) 0.0393(9) Uani 1 1 d . . . H16 H 0.0604 1.1256 0.4372 0.047 Uiso 1 1 calc R . . C17 C -0.0918(5) 0.6892(2) 0.30503(17) 0.0360(8) Uani 1 1 d . . . H17 H -0.1573 0.6498 0.2778 0.043 Uiso 1 1 calc R . . C18 C -0.1794(4) 0.7402(2) 0.34961(17) 0.0349(8) Uani 1 1 d . . . H18 H -0.3004 0.7363 0.3508 0.042 Uiso 1 1 calc R . . C19 C -0.0842(4) 0.7974(2) 0.39285(16) 0.0315(8) Uani 1 1 d . . . C20 C 0.0945(4) 0.8051(2) 0.38366(18) 0.0368(9) Uani 1 1 d . . . H20 H 0.1635 0.8450 0.4092 0.044 Uiso 1 1 calc R . . C21 C 0.1674(4) 0.7531(2) 0.33646(18) 0.0393(9) Uani 1 1 d . . . H21 H 0.2862 0.7605 0.3307 0.047 Uiso 1 1 calc R . . C22 C -0.4870(5) 0.6904(3) 0.5107(2) 0.0562(12) Uani 1 1 d . . . H22 H -0.5059 0.6277 0.5140 0.067 Uiso 1 1 calc R . . C23 C -0.3421(5) 0.7177(2) 0.48038(18) 0.0433(10) Uani 1 1 d . . . H23 H -0.2640 0.6748 0.4654 0.052 Uiso 1 1 calc R . . C24 C -0.3133(4) 0.8101(2) 0.47222(17) 0.0322(8) Uani 1 1 d . . . C25 C -0.4321(5) 0.8692(3) 0.4980(2) 0.0521(11) Uani 1 1 d . . . H25 H -0.4181 0.9321 0.4944 0.063 Uiso 1 1 calc R . . C26 C -0.5710(5) 0.8338(3) 0.5292(2) 0.0616(13) Uani 1 1 d . . . H26 H -0.6479 0.8750 0.5469 0.074 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 0.0356(3) 0.0385(3) 0.0414(3) 0.0012(2) 0.0020(2) 0.00126(19) I1 0.05433(19) 0.0688(2) 0.0585(2) -0.00844(16) -0.00970(14) -0.01755(14) N1 0.0346(17) 0.0320(15) 0.0319(17) -0.0088(14) -0.0073(13) 0.0052(12) N2 0.0341(17) 0.0364(16) 0.0324(17) 0.0035(14) 0.0032(14) -0.0024(13) N3 0.0358(17) 0.0319(15) 0.0364(18) -0.0011(14) 0.0024(14) 0.0010(13) N4 0.0334(16) 0.0304(15) 0.0404(18) -0.0064(14) 0.0096(14) -0.0057(12) N5 0.0374(18) 0.0349(15) 0.0311(17) 0.0013(14) 0.0062(14) -0.0005(13) N6 0.056(2) 0.063(2) 0.067(3) -0.022(2) 0.0273(19) -0.0219(18) C1 0.0242(18) 0.0309(17) 0.030(2) -0.0054(16) -0.0030(15) 0.0054(14) C2 0.0315(19) 0.0290(17) 0.041(2) -0.0005(17) -0.0037(16) -0.0057(15) C3 0.040(2) 0.0351(18) 0.029(2) 0.0020(17) -0.0001(17) -0.0022(16) C4 0.0259(19) 0.053(2) 0.055(3) 0.016(2) 0.0032(18) -0.0003(17) C5 0.032(2) 0.044(2) 0.053(3) 0.014(2) 0.0022(18) 0.0043(16) C6 0.034(2) 0.0297(17) 0.027(2) 0.0027(16) -0.0014(15) -0.0054(14) C7 0.0274(18) 0.0359(19) 0.037(2) 0.0035(17) -0.0040(15) -0.0005(15) C8 0.036(2) 0.0304(18) 0.032(2) 0.0022(16) -0.0014(16) 0.0012(15) C9 0.046(2) 0.0365(19) 0.029(2) -0.0048(17) -0.0053(17) 0.0001(17) C10 0.039(2) 0.0348(18) 0.033(2) -0.0055(17) -0.0005(17) 0.0071(16) C11 0.0283(19) 0.0239(16) 0.035(2) -0.0026(16) 0.0012(16) -0.0028(14) C12 0.035(2) 0.0350(18) 0.030(2) -0.0062(17) -0.0029(16) -0.0001(15) C13 0.034(2) 0.0343(18) 0.035(2) -0.0061(18) 0.0016(17) 0.0032(15) C14 0.032(2) 0.0269(17) 0.037(2) -0.0078(17) 0.0061(17) -0.0018(14) C15 0.048(2) 0.042(2) 0.026(2) 0.0002(18) 0.0007(17) -0.0050(17) C16 0.051(2) 0.0315(19) 0.036(2) 0.0052(18) 0.0044(18) -0.0097(17) C17 0.038(2) 0.0397(19) 0.030(2) -0.0009(17) -0.0017(17) -0.0018(16) C18 0.0271(18) 0.042(2) 0.035(2) -0.0031(18) 0.0003(16) -0.0035(15) C19 0.035(2) 0.0274(17) 0.032(2) 0.0025(16) 0.0045(16) 0.0006(15) C20 0.034(2) 0.0335(18) 0.043(2) -0.0072(18) 0.0001(17) -0.0062(15) C21 0.0297(19) 0.040(2) 0.049(2) 0.0007(19) 0.0086(18) -0.0018(16) C22 0.062(3) 0.047(2) 0.062(3) -0.010(2) 0.025(2) -0.020(2) C23 0.049(2) 0.035(2) 0.048(2) -0.0045(19) 0.020(2) -0.0014(17) C24 0.0306(19) 0.0327(18) 0.034(2) -0.0035(16) 0.0037(16) -0.0041(15) C25 0.042(2) 0.039(2) 0.077(3) -0.009(2) 0.022(2) 0.0004(18) C26 0.045(3) 0.059(3) 0.083(4) -0.024(3) 0.024(2) -0.003(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 N3 2.086(3) . ? Cu1 N5 2.090(3) . ? Cu1 N2 2.106(3) . ? Cu1 I1 2.5623(5) . ? N1 C11 1.394(4) . ? N1 C6 1.424(4) 2_645 ? N1 C1 1.441(4) . ? N2 C8 1.329(4) . ? N2 C4 1.341(4) . ? N3 C13 1.327(4) . ? N3 C9 1.342(4) . ? N4 C19 1.400(4) . ? N4 C24 1.416(4) . ? N4 C14 1.439(4) . ? N5 C17 1.330(4) . ? N5 C21 1.334(4) . ? N6 C26 1.326(5) . ? N6 C22 1.329(5) . ? C1 C2 1.377(5) . ? C1 C3 1.394(4) 3_766 ? C2 C3 1.388(5) . ? C2 H2 0.9300 . ? C3 C1 1.394(4) 3_766 ? C3 H3 0.9300 . ? C4 C5 1.373(5) . ? C4 H4 0.9300 . ? C5 C6 1.385(4) . ? C5 H5 0.9300 . ? C6 C7 1.383(4) . ? C6 N1 1.424(4) 2_655 ? C7 C8 1.382(4) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.363(5) . ? C9 H9 0.9300 . ? C10 C11 1.394(5) . ? C10 H10 0.9300 . ? C11 C12 1.403(4) . ? C12 C13 1.374(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C16 1.377(5) 3_576 ? C14 C15 1.387(4) . ? C15 C16 1.385(5) . ? C15 H15 0.9300 . ? C16 C14 1.377(5) 3_576 ? C16 H16 0.9300 . ? C17 C18 1.382(4) . ? C17 H17 0.9300 . ? C18 C19 1.396(5) . ? C18 H18 0.9300 . ? C19 C20 1.396(4) . ? C20 C21 1.374(4) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.362(5) . ? C22 H22 0.9300 . ? C23 C24 1.380(4) . ? C23 H23 0.9300 . ? C24 C25 1.381(4) . ? C25 C26 1.373(5) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? 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 N5 111.69(11) . . ? N3 Cu1 N2 102.81(11) . . ? N5 Cu1 N2 98.12(10) . . ? N3 Cu1 I1 110.32(8) . . ? N5 Cu1 I1 114.48(8) . . ? N2 Cu1 I1 118.43(8) . . ? C11 N1 C6 123.3(3) . 2_645 ? C11 N1 C1 119.1(2) . . ? C6 N1 C1 117.6(3) 2_645 . ? C8 N2 C4 115.9(3) . . ? C8 N2 Cu1 124.9(2) . . ? C4 N2 Cu1 118.5(2) . . ? C13 N3 C9 114.9(3) . . ? C13 N3 Cu1 125.3(2) . . ? C9 N3 Cu1 118.7(2) . . ? C19 N4 C24 122.4(3) . . ? C19 N4 C14 119.8(3) . . ? C24 N4 C14 117.2(3) . . ? C17 N5 C21 115.7(3) . . ? C17 N5 Cu1 122.1(2) . . ? C21 N5 Cu1 121.7(2) . . ? C26 N6 C22 114.3(3) . . ? C2 C1 C3 119.9(3) . 3_766 ? C2 C1 N1 119.7(3) . . ? C3 C1 N1 120.4(3) 3_766 . ? C1 C2 C3 120.2(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C1 119.9(3) . 3_766 ? C2 C3 H3 120.1 . . ? C1 C3 H3 120.1 3_766 . ? N2 C4 C5 124.0(3) . . ? N2 C4 H4 118.0 . . ? C5 C4 H4 118.0 . . ? C4 C5 C6 119.4(3) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C5 117.4(3) . . ? C7 C6 N1 122.3(3) . 2_655 ? C5 C6 N1 120.3(3) . 2_655 ? C8 C7 C6 119.0(3) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? N2 C8 C7 124.3(3) . . ? N2 C8 H8 117.8 . . ? C7 C8 H8 117.8 . . ? N3 C9 C10 124.9(3) . . ? N3 C9 H9 117.6 . . ? C10 C9 H9 117.6 . . ? C9 C10 C11 119.9(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 N1 123.7(3) . . ? C10 C11 C12 115.9(3) . . ? N1 C11 C12 120.4(3) . . ? C13 C12 C11 119.2(3) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? N3 C13 C12 125.2(3) . . ? N3 C13 H13 117.4 . . ? C12 C13 H13 117.4 . . ? C16 C14 C15 119.8(3) 3_576 . ? C16 C14 N4 119.9(3) 3_576 . ? C15 C14 N4 120.3(3) . . ? C16 C15 C14 119.3(3) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C14 C16 C15 120.9(3) 3_576 . ? C14 C16 H16 119.5 3_576 . ? C15 C16 H16 119.5 . . ? N5 C17 C18 124.4(3) . . ? N5 C17 H17 117.8 . . ? C18 C17 H17 117.8 . . ? C17 C18 C19 119.2(3) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C18 C19 C20 116.4(3) . . ? C18 C19 N4 121.5(3) . . ? C20 C19 N4 122.1(3) . . ? C21 C20 C19 119.4(3) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? N5 C21 C20 124.6(3) . . ? N5 C21 H21 117.7 . . ? C20 C21 H21 117.7 . . ? N6 C22 C23 125.8(4) . . ? N6 C22 H22 117.1 . . ? C23 C22 H22 117.1 . . ? C22 C23 C24 118.8(3) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C23 C24 C25 116.9(3) . . ? C23 C24 N4 122.6(3) . . ? C25 C24 N4 120.5(3) . . ? C26 C25 C24 119.2(3) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? N6 C26 C25 124.9(4) . . ? N6 C26 H26 117.5 . . ? C25 C26 H26 117.5 . . ? 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 N3 Cu1 N2 C8 9.9(3) . . . . ? N5 Cu1 N2 C8 124.4(3) . . . . ? I1 Cu1 N2 C8 -112.0(3) . . . . ? N3 Cu1 N2 C4 -160.5(3) . . . . ? N5 Cu1 N2 C4 -46.0(3) . . . . ? I1 Cu1 N2 C4 77.6(3) . . . . ? N5 Cu1 N3 C13 -11.4(3) . . . . ? N2 Cu1 N3 C13 92.9(3) . . . . ? I1 Cu1 N3 C13 -139.9(3) . . . . ? N5 Cu1 N3 C9 -178.8(2) . . . . ? N2 Cu1 N3 C9 -74.5(3) . . . . ? I1 Cu1 N3 C9 52.7(3) . . . . ? N3 Cu1 N5 C17 -119.8(3) . . . . ? N2 Cu1 N5 C17 132.8(3) . . . . ? I1 Cu1 N5 C17 6.5(3) . . . . ? N3 Cu1 N5 C21 51.8(3) . . . . ? N2 Cu1 N5 C21 -55.5(3) . . . . ? I1 Cu1 N5 C21 178.1(2) . . . . ? C11 N1 C1 C2 105.4(3) . . . . ? C6 N1 C1 C2 -75.4(4) 2_645 . . . ? C11 N1 C1 C3 -73.8(4) . . . 3_766 ? C6 N1 C1 C3 105.3(3) 2_645 . . 3_766 ? C3 C1 C2 C3 0.5(5) 3_766 . . . ? N1 C1 C2 C3 -178.7(3) . . . . ? C1 C2 C3 C1 -0.5(5) . . . 3_766 ? C8 N2 C4 C5 -2.2(5) . . . . ? Cu1 N2 C4 C5 169.0(3) . . . . ? N2 C4 C5 C6 0.1(6) . . . . ? C4 C5 C6 C7 2.2(5) . . . . ? C4 C5 C6 N1 -178.8(3) . . . 2_655 ? C5 C6 C7 C8 -2.3(5) . . . . ? N1 C6 C7 C8 178.7(3) 2_655 . . . ? C4 N2 C8 C7 2.1(5) . . . . ? Cu1 N2 C8 C7 -168.5(3) . . . . ? C6 C7 C8 N2 0.2(5) . . . . ? C13 N3 C9 C10 -2.1(5) . . . . ? Cu1 N3 C9 C10 166.6(3) . . . . ? N3 C9 C10 C11 1.7(5) . . . . ? C9 C10 C11 N1 -176.8(3) . . . . ? C9 C10 C11 C12 0.4(5) . . . . ? C6 N1 C11 C10 -14.9(5) 2_645 . . . ? C1 N1 C11 C10 164.1(3) . . . . ? C6 N1 C11 C12 168.0(3) 2_645 . . . ? C1 N1 C11 C12 -12.9(4) . . . . ? C10 C11 C12 C13 -1.8(5) . . . . ? N1 C11 C12 C13 175.5(3) . . . . ? C9 N3 C13 C12 0.5(5) . . . . ? Cu1 N3 C13 C12 -167.3(3) . . . . ? C11 C12 C13 N3 1.4(5) . . . . ? C19 N4 C14 C16 -120.3(3) . . . 3_576 ? C24 N4 C14 C16 51.0(4) . . . 3_576 ? C19 N4 C14 C15 59.3(4) . . . . ? C24 N4 C14 C15 -129.4(3) . . . . ? C16 C14 C15 C16 -0.4(6) 3_576 . . . ? N4 C14 C15 C16 -180.0(3) . . . . ? C14 C15 C16 C14 0.4(6) . . . 3_576 ? C21 N5 C17 C18 -2.7(5) . . . . ? Cu1 N5 C17 C18 169.4(3) . . . . ? N5 C17 C18 C19 -2.5(5) . . . . ? C17 C18 C19 C20 5.6(5) . . . . ? C17 C18 C19 N4 -174.5(3) . . . . ? C24 N4 C19 C18 29.9(5) . . . . ? C14 N4 C19 C18 -159.3(3) . . . . ? C24 N4 C19 C20 -150.3(3) . . . . ? C14 N4 C19 C20 20.5(5) . . . . ? C18 C19 C20 C21 -3.9(5) . . . . ? N4 C19 C20 C21 176.3(3) . . . . ? C17 N5 C21 C20 4.6(5) . . . . ? Cu1 N5 C21 C20 -167.5(3) . . . . ? C19 C20 C21 N5 -1.4(5) . . . . ? C26 N6 C22 C23 0.7(7) . . . . ? N6 C22 C23 C24 -2.6(7) . . . . ? C22 C23 C24 C25 2.4(6) . . . . ? C22 C23 C24 N4 178.6(4) . . . . ? C19 N4 C24 C23 32.3(5) . . . . ? C14 N4 C24 C23 -138.7(4) . . . . ? C19 N4 C24 C25 -151.6(4) . . . . ? C14 N4 C24 C25 37.4(5) . . . . ? C23 C24 C25 C26 -0.7(6) . . . . ? N4 C24 C25 C26 -177.0(4) . . . . ? C22 N6 C26 C25 1.2(7) . . . . ? C24 C25 C26 N6 -1.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.920 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 939482' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110507b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 N6 O8 Zn2' _chemical_formula_weight 727.29 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' Zn Zn 0.2839 1.4301 '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 10.7980(11) _cell_length_b 9.0501(9) _cell_length_c 15.7801(15) _cell_angle_alpha 90.00 _cell_angle_beta 102.5500(10) _cell_angle_gamma 90.00 _cell_volume 1505.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 682 _cell_measurement_theta_min 2.609 _cell_measurement_theta_max 26.211 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 1.655 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6365 _exptl_absorpt_correction_T_max 0.8136 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 '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 6857 _diffrn_reflns_av_R_equivalents 0.1676 _diffrn_reflns_av_sigmaI/netI 0.2090 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 24.15 _reflns_number_total 2376 _reflns_number_gt 944 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1192P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2376 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1579 _refine_ls_R_factor_gt 0.0812 _refine_ls_wR_factor_ref 0.2237 _refine_ls_wR_factor_gt 0.1825 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _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 Zn1 Zn 0.88533(11) 0.47409(16) 0.11142(9) 0.0644(7) Uani 1 1 d . . . N1 N 0.4497(7) 0.4869(10) 0.3172(5) 0.052(2) Uani 1 1 d . . . N2 N 0.7503(8) 0.4884(10) 0.1843(6) 0.055(2) Uani 1 1 d . . . N3 N 1.0676(8) 0.4835(11) 0.1901(6) 0.060(3) Uani 1 1 d . . . O1 O 0.8395(10) 0.3046(11) 0.0348(7) 0.097(3) Uani 1 1 d . . . O2 O 0.9532(13) 0.1681(12) 0.1291(9) 0.145(5) Uani 1 1 d . . . O3 O 0.8958(8) 0.6518(11) 0.0452(7) 0.095(3) Uani 1 1 d . . . O4 O 0.6955(10) 0.6483(13) -0.0209(7) 0.115(4) Uani 1 1 d . . . C1 C 0.4767(10) 0.4908(12) 0.4098(7) 0.049(3) Uani 1 1 d . . . C2 C 0.5552(12) 0.3911(15) 0.4608(8) 0.072(4) Uani 1 1 d . . . H2 H 0.5942 0.3169 0.4352 0.086 Uiso 1 1 calc R . . C3 C 0.5763(12) 0.4008(15) 0.5498(8) 0.068(4) Uani 1 1 d . . . H3 H 0.6283 0.3312 0.5834 0.082 Uiso 1 1 calc R . . C4 C 0.7691(10) 0.5194(13) 0.2690(8) 0.063(3) Uani 1 1 d . . . H4 H 0.8518 0.5379 0.2988 0.075 Uiso 1 1 calc R . . C5 C 0.6728(9) 0.5259(11) 0.3161(7) 0.049(3) Uani 1 1 d . . . H5 H 0.6896 0.5525 0.3744 0.058 Uiso 1 1 calc R . . C6 C 0.5505(9) 0.4902(12) 0.2708(6) 0.046(3) Uani 1 1 d . . . C7 C 0.5285(8) 0.4583(13) 0.1828(7) 0.058(3) Uani 1 1 d . . . H7 H 0.4470 0.4352 0.1525 0.070 Uiso 1 1 calc R . . C8 C 0.6262(9) 0.4608(12) 0.1409(7) 0.054(3) Uani 1 1 d . . . H8 H 0.6093 0.4436 0.0814 0.065 Uiso 1 1 calc R . . C9 C 1.1488(10) 0.5823(13) 0.1664(7) 0.060(3) Uani 1 1 d . . . H9 H 1.1167 0.6509 0.1234 0.072 Uiso 1 1 calc R . . C10 C 1.2758(10) 0.5847(14) 0.2035(7) 0.060(3) Uani 1 1 d . . . H10 H 1.3300 0.6479 0.1825 0.073 Uiso 1 1 calc R . . C11 C 1.3225(10) 0.4909(12) 0.2731(7) 0.056(3) Uani 1 1 d . . . C12 C 1.2339(10) 0.3945(14) 0.2989(7) 0.062(3) Uani 1 1 d . . . H12 H 1.2604 0.3303 0.3454 0.075 Uiso 1 1 calc R . . C13 C 1.1118(10) 0.3957(14) 0.2564(8) 0.066(3) Uani 1 1 d . . . H13 H 1.0556 0.3315 0.2747 0.079 Uiso 1 1 calc R . . C14 C 0.8877(13) 0.186(2) 0.0551(10) 0.089(5) Uani 1 1 d . . . H14 H 0.8757 0.1088 0.0154 0.106 Uiso 1 1 calc R . . C15 C 0.7993(15) 0.6908(17) -0.0075(9) 0.087(4) Uani 1 1 d . . . H15 H 0.8122 0.7687 -0.0431 0.104 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 Zn1 0.0351(8) 0.1041(13) 0.0545(10) 0.0078(9) 0.0108(6) -0.0006(7) N1 0.031(4) 0.098(7) 0.028(5) 0.002(5) 0.009(3) 0.001(4) N2 0.039(5) 0.086(7) 0.041(6) -0.005(5) 0.012(4) -0.004(4) N3 0.036(5) 0.090(7) 0.053(6) 0.012(6) 0.010(4) -0.007(5) O1 0.088(7) 0.104(8) 0.101(8) 0.021(7) 0.025(6) 0.006(6) O2 0.139(11) 0.136(10) 0.142(11) 0.026(9) -0.010(9) -0.031(8) O3 0.048(5) 0.123(8) 0.107(8) 0.027(6) 0.000(5) -0.006(5) O4 0.060(7) 0.182(11) 0.095(8) 0.011(8) -0.002(5) -0.002(7) C1 0.052(6) 0.063(8) 0.033(6) -0.010(6) 0.011(5) -0.001(5) C2 0.075(9) 0.084(9) 0.062(9) 0.006(8) 0.027(7) 0.019(7) C3 0.078(9) 0.088(10) 0.040(8) 0.003(8) 0.012(6) 0.013(7) C4 0.038(6) 0.096(9) 0.054(8) -0.010(7) 0.010(5) -0.003(6) C5 0.043(6) 0.060(7) 0.040(6) -0.008(6) 0.005(5) -0.007(5) C6 0.038(5) 0.084(8) 0.018(5) -0.001(5) 0.015(4) 0.003(5) C7 0.014(5) 0.102(9) 0.055(8) -0.003(7) 0.002(4) -0.005(5) C8 0.041(6) 0.092(9) 0.031(6) 0.001(6) 0.012(4) 0.005(6) C9 0.039(6) 0.078(8) 0.065(8) 0.026(7) 0.017(5) 0.009(6) C10 0.049(7) 0.095(9) 0.037(7) 0.014(7) 0.009(5) -0.008(6) C11 0.043(6) 0.084(9) 0.044(7) -0.008(7) 0.018(5) -0.004(6) C12 0.037(6) 0.085(8) 0.065(8) 0.019(7) 0.013(5) -0.005(6) C13 0.046(7) 0.092(9) 0.058(8) 0.014(8) 0.006(6) -0.017(6) C14 0.065(10) 0.119(14) 0.069(11) 0.016(10) -0.015(8) -0.013(9) C15 0.066(10) 0.116(12) 0.078(11) 0.017(9) 0.015(8) 0.003(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 Zn1 O3 1.934(10) . ? Zn1 O1 1.949(10) . ? Zn1 N2 2.047(9) . ? Zn1 N3 2.089(9) . ? N1 C11 1.399(12) 1_455 ? N1 C1 1.427(13) . ? N1 C6 1.438(11) . ? N2 C4 1.337(14) . ? N2 C8 1.389(13) . ? N3 C13 1.317(13) . ? N3 C9 1.360(13) . ? O1 C14 1.204(16) . ? O2 C14 1.237(16) . ? O3 C15 1.236(15) . ? O4 C15 1.160(15) . ? C1 C3 1.361(15) 3_666 ? C1 C2 1.374(15) . ? C2 C3 1.374(16) . ? C2 H2 0.9300 . ? C3 C1 1.361(15) 3_666 ? C3 H3 0.9300 . ? C4 C5 1.405(15) . ? C4 H4 0.9300 . ? C5 C6 1.395(13) . ? C5 H5 0.9300 . ? C6 C7 1.387(14) . ? C7 C8 1.361(14) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.369(14) . ? C9 H9 0.9300 . ? C10 C11 1.393(15) . ? C10 H10 0.9300 . ? C11 N1 1.399(12) 1_655 ? C11 C12 1.418(15) . ? C12 C13 1.343(14) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O1 110.8(5) . . ? O3 Zn1 N2 112.5(4) . . ? O1 Zn1 N2 106.4(4) . . ? O3 Zn1 N3 97.4(4) . . ? O1 Zn1 N3 118.7(4) . . ? N2 Zn1 N3 110.9(4) . . ? C11 N1 C1 117.9(8) 1_455 . ? C11 N1 C6 121.1(8) 1_455 . ? C1 N1 C6 120.8(8) . . ? C4 N2 C8 116.8(9) . . ? C4 N2 Zn1 127.1(7) . . ? C8 N2 Zn1 116.1(7) . . ? C13 N3 C9 118.1(9) . . ? C13 N3 Zn1 125.4(8) . . ? C9 N3 Zn1 116.3(7) . . ? C14 O1 Zn1 119.9(11) . . ? C15 O3 Zn1 117.5(9) . . ? C3 C1 C2 117.9(10) 3_666 . ? C3 C1 N1 119.0(10) 3_666 . ? C2 C1 N1 123.1(11) . . ? C1 C2 C3 120.0(12) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C1 C3 C2 122.1(12) 3_666 . ? C1 C3 H3 118.9 3_666 . ? C2 C3 H3 118.9 . . ? N2 C4 C5 124.7(10) . . ? N2 C4 H4 117.7 . . ? C5 C4 H4 117.7 . . ? C6 C5 C4 116.5(10) . . ? C6 C5 H5 121.8 . . ? C4 C5 H5 121.8 . . ? C7 C6 C5 119.9(8) . . ? C7 C6 N1 121.4(8) . . ? C5 C6 N1 118.7(8) . . ? C8 C7 C6 120.0(9) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 N2 122.0(10) . . ? C7 C8 H8 119.0 . . ? N2 C8 H8 119.0 . . ? N3 C9 C10 122.5(10) . . ? N3 C9 H9 118.7 . . ? C10 C9 H9 118.7 . . ? C9 C10 C11 119.0(11) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C10 C11 N1 123.8(10) . 1_655 ? C10 C11 C12 116.7(10) . . ? N1 C11 C12 119.5(10) 1_655 . ? C13 C12 C11 120.1(11) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? N3 C13 C12 123.2(11) . . ? N3 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? O1 C14 O2 119.7(17) . . ? O1 C14 H14 120.2 . . ? O2 C14 H14 120.2 . . ? O4 C15 O3 131.9(15) . . ? O4 C15 H15 114.1 . . ? O3 C15 H15 114.1 . . ? 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 O3 Zn1 N2 C4 -99.4(10) . . . . ? O1 Zn1 N2 C4 139.0(10) . . . . ? N3 Zn1 N2 C4 8.6(11) . . . . ? O3 Zn1 N2 C8 81.5(8) . . . . ? O1 Zn1 N2 C8 -40.1(8) . . . . ? N3 Zn1 N2 C8 -170.5(7) . . . . ? O3 Zn1 N3 C13 172.6(10) . . . . ? O1 Zn1 N3 C13 -68.6(11) . . . . ? N2 Zn1 N3 C13 55.0(11) . . . . ? O3 Zn1 N3 C9 -12.0(9) . . . . ? O1 Zn1 N3 C9 106.7(9) . . . . ? N2 Zn1 N3 C9 -129.6(8) . . . . ? O3 Zn1 O1 C14 141.5(12) . . . . ? N2 Zn1 O1 C14 -95.9(12) . . . . ? N3 Zn1 O1 C14 30.0(14) . . . . ? O1 Zn1 O3 C15 59.5(11) . . . . ? N2 Zn1 O3 C15 -59.5(11) . . . . ? N3 Zn1 O3 C15 -175.9(10) . . . . ? C11 N1 C1 C3 -51.6(14) 1_455 . . 3_666 ? C6 N1 C1 C3 123.7(12) . . . 3_666 ? C11 N1 C1 C2 129.2(12) 1_455 . . . ? C6 N1 C1 C2 -55.5(15) . . . . ? C3 C1 C2 C3 1(2) 3_666 . . . ? N1 C1 C2 C3 -179.5(11) . . . . ? C1 C2 C3 C1 -1(2) . . . 3_666 ? C8 N2 C4 C5 -0.1(17) . . . . ? Zn1 N2 C4 C5 -179.1(9) . . . . ? N2 C4 C5 C6 3.1(18) . . . . ? C4 C5 C6 C7 -3.2(16) . . . . ? C4 C5 C6 N1 176.5(10) . . . . ? C11 N1 C6 C7 -17.4(16) 1_455 . . . ? C1 N1 C6 C7 167.5(10) . . . . ? C11 N1 C6 C5 162.9(10) 1_455 . . . ? C1 N1 C6 C5 -12.2(15) . . . . ? C5 C6 C7 C8 0.4(17) . . . . ? N1 C6 C7 C8 -179.3(10) . . . . ? C6 C7 C8 N2 2.9(18) . . . . ? C4 N2 C8 C7 -3.0(16) . . . . ? Zn1 N2 C8 C7 176.1(9) . . . . ? C13 N3 C9 C10 6.0(18) . . . . ? Zn1 N3 C9 C10 -169.6(9) . . . . ? N3 C9 C10 C11 -5.5(18) . . . . ? C9 C10 C11 N1 -178.3(10) . . . 1_655 ? C9 C10 C11 C12 2.2(16) . . . . ? C10 C11 C12 C13 0.5(17) . . . . ? N1 C11 C12 C13 -179.1(11) 1_655 . . . ? C9 N3 C13 C12 -3.2(18) . . . . ? Zn1 N3 C13 C12 172.0(9) . . . . ? C11 C12 C13 N3 0.1(19) . . . . ? Zn1 O1 C14 O2 9(2) . . . . ? Zn1 O3 C15 O4 8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.15 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.107 _refine_diff_density_min -0.961 _refine_diff_density_rms 0.137 _database_code_depnum_ccdc_archive 'CCDC 939483' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110504e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H44 Ag4 N24 O2' _chemical_formula_weight 1468.59 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' Ag Ag -0.8971 1.1015 '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)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 11.1740(12) _cell_length_b 15.3189(17) _cell_length_c 15.2751(15) _cell_angle_alpha 90.00 _cell_angle_beta 93.7650(10) _cell_angle_gamma 90.00 _cell_volume 2609.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1812 _cell_measurement_theta_min 2.563 _cell_measurement_theta_max 23.546 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 1.549 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5907 _exptl_absorpt_correction_T_max 0.9128 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 '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 12040 _diffrn_reflns_av_R_equivalents 0.1509 _diffrn_reflns_av_sigmaI/netI 0.1318 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 24.15 _reflns_number_total 4190 _reflns_number_gt 2201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.2000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4190 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1478 _refine_ls_R_factor_gt 0.0899 _refine_ls_wR_factor_ref 0.2375 _refine_ls_wR_factor_gt 0.1994 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 Ag1 Ag 0.12214(14) 0.63553(10) 0.38057(12) 0.0531(7) Uani 1 1 d . . . Ag2 Ag 0.64472(13) 0.63572(10) 0.13034(11) 0.0518(7) Uani 1 1 d . . . N1 N 0.6215(12) 0.4318(9) 0.3707(9) 0.034(4) Uani 1 1 d . . . N2 N 0.2864(14) 0.5576(9) 0.3523(10) 0.040(4) Uani 1 1 d . . . N3 N 0.9544(14) 0.5553(10) 0.3954(10) 0.044(4) Uani 1 1 d . . . N4 N 0.149(2) 0.7500 0.271(2) 0.051(7) Uani 1 2 d S . . N5 N 0.149(2) 0.7500 0.200(3) 0.052(7) Uani 1 2 d S . . N6 N 0.137(3) 0.7500 0.122(2) 0.071(9) Uani 1 2 d S . . N7 N 0.081(2) 0.7500 0.4729(16) 0.047(6) Uani 1 2 d S . . N8 N 0.027(2) 0.7500 0.5334(18) 0.051(6) Uani 1 2 d S . . N9 N -0.027(3) 0.7500 0.5926(19) 0.071(8) Uani 1 2 d S . . N10 N 0.1450(12) 0.4320(9) 0.1308(9) 0.036(4) Uani 1 1 d . . . N11 N 0.4751(13) 0.5536(9) 0.1072(10) 0.039(4) Uani 1 1 d . . . N12 N -0.1843(12) 0.5594(8) 0.1481(10) 0.032(3) Uani 1 1 d . . . N13 N 0.662(3) 0.7500 0.239(2) 0.060(8) Uani 1 2 d S . . N14 N 0.644(2) 0.7500 0.305(3) 0.057(8) Uani 1 2 d S . . N15 N 0.617(2) 0.7500 0.3845(19) 0.060(8) Uani 1 2 d S . . N16 N 0.600(2) 0.7500 0.0335(16) 0.043(6) Uani 1 2 d S . . N17 N 0.526(2) 0.7500 -0.0272(18) 0.049(6) Uani 1 2 d S . . N18 N 0.453(3) 0.7500 -0.082(2) 0.071(8) Uani 1 2 d S . . O1 O 0.715(2) 0.7500 0.5640(15) 0.074(7) Uani 1 2 d S . . H1C H 0.7917 0.7500 0.5685 0.089 Uiso 1 2 d SR . . H1D H 0.6924 0.7500 0.5098 0.089 Uiso 1 2 d SR . . O2 O 0.197(2) 0.7500 0.9419(18) 0.091(8) Uani 1 2 d S . . H2C H 0.1822 0.7500 0.9959 0.110 Uiso 1 2 d SR . . H2D H 0.2721 0.7500 0.9382 0.110 Uiso 1 2 d SR . . C1 C 0.6207(15) 0.3395(12) 0.3702(11) 0.035(4) Uani 1 1 d . . . C2 C 0.6390(16) 0.2946(11) 0.4459(12) 0.040(5) Uani 1 1 d . . . H2 H 0.6517 0.3246 0.4986 0.048 Uiso 1 1 calc R . . C3 C 0.5953(16) 0.2941(11) 0.2933(12) 0.039(4) Uani 1 1 d . . . H3 H 0.5781 0.3243 0.2412 0.046 Uiso 1 1 calc R . . C4 C 0.3058(17) 0.4775(12) 0.3859(12) 0.041(5) Uani 1 1 d . . . H4 H 0.2414 0.4509 0.4108 0.049 Uiso 1 1 calc R . . C5 C 0.4071(16) 0.4324(12) 0.3872(12) 0.038(4) Uani 1 1 d . . . H5 H 0.4078 0.3734 0.4016 0.045 Uiso 1 1 calc R . . C6 C 0.5129(16) 0.4742(11) 0.3669(12) 0.037(5) Uani 1 1 d . . . C7 C 0.4935(15) 0.5575(10) 0.3299(11) 0.034(4) Uani 1 1 d . . . H7 H 0.5574 0.5872 0.3077 0.041 Uiso 1 1 calc R . . C8 C 0.3870(16) 0.5941(11) 0.3260(12) 0.039(4) Uani 1 1 d . . . H8 H 0.3808 0.6502 0.3029 0.047 Uiso 1 1 calc R . . C9 C 0.9341(18) 0.4701(13) 0.3685(13) 0.046(5) Uani 1 1 d . . . H9 H 1.0013 0.4391 0.3535 0.055 Uiso 1 1 calc R . . C10 C 0.8333(16) 0.4282(12) 0.3616(12) 0.039(5) Uani 1 1 d . . . H10 H 0.8323 0.3694 0.3466 0.046 Uiso 1 1 calc R . . C11 C 0.7265(16) 0.4708(12) 0.3766(11) 0.035(4) Uani 1 1 d . . . C12 C 0.7476(17) 0.5593(12) 0.4078(13) 0.042(5) Uani 1 1 d . . . H12 H 0.6835 0.5916 0.4265 0.051 Uiso 1 1 calc R . . C13 C 0.8556(17) 0.5957(13) 0.4105(13) 0.045(5) Uani 1 1 d . . . H13 H 0.8610 0.6547 0.4243 0.054 Uiso 1 1 calc R . . C14 C 0.1399(15) 0.3395(11) 0.1311(12) 0.036(5) Uani 1 1 d . . . C15 C 0.1314(16) 0.2942(11) 0.2084(13) 0.044(5) Uani 1 1 d . . . H15 H 0.1256 0.3245 0.2607 0.052 Uiso 1 1 calc R . . C16 C 0.1554(16) 0.2951(11) 0.0532(13) 0.041(5) Uani 1 1 d . . . H16 H 0.1656 0.3258 0.0017 0.050 Uiso 1 1 calc R . . C17 C 0.4647(16) 0.4704(11) 0.1285(12) 0.038(5) Uani 1 1 d . . . H17 H 0.5352 0.4387 0.1388 0.046 Uiso 1 1 calc R . . C18 C 0.3593(15) 0.4271(11) 0.1365(11) 0.035(4) Uani 1 1 d . . . H18 H 0.3584 0.3681 0.1505 0.042 Uiso 1 1 calc R . . C19 C 0.2547(16) 0.4735(11) 0.1233(12) 0.036(5) Uani 1 1 d . . . C20 C 0.2633(17) 0.5587(11) 0.0969(12) 0.040(5) Uani 1 1 d . . . H20 H 0.1947 0.5915 0.0829 0.048 Uiso 1 1 calc R . . C21 C 0.3750(16) 0.5944(12) 0.0915(13) 0.041(5) Uani 1 1 d . . . H21 H 0.3789 0.6527 0.0751 0.050 Uiso 1 1 calc R . . C22 C -0.0828(15) 0.5975(12) 0.1752(12) 0.039(5) Uani 1 1 d . . . H22 H -0.0848 0.6538 0.1979 0.047 Uiso 1 1 calc R . . C23 C 0.0240(16) 0.5572(10) 0.1710(12) 0.036(4) Uani 1 1 d . . . H23 H 0.0928 0.5847 0.1949 0.043 Uiso 1 1 calc R . . C24 C 0.0344(16) 0.4766(11) 0.1325(12) 0.036(5) Uani 1 1 d . . . C25 C -0.0677(15) 0.4348(11) 0.1097(12) 0.037(4) Uani 1 1 d . . . H25 H -0.0673 0.3774 0.0898 0.044 Uiso 1 1 calc R . . C26 C -0.1737(17) 0.4795(11) 0.1164(12) 0.040(5) Uani 1 1 d . . . H26 H -0.2440 0.4511 0.0970 0.048 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 Ag1 0.0380(11) 0.0343(10) 0.0885(14) -0.0047(7) 0.0151(9) 0.0002(7) Ag2 0.0300(10) 0.0344(10) 0.0906(14) 0.0040(7) 0.0011(8) 0.0025(6) N1 0.029(9) 0.022(8) 0.052(10) -0.001(6) 0.006(7) -0.003(6) N2 0.040(10) 0.022(8) 0.058(11) -0.006(7) 0.003(8) -0.002(7) N3 0.037(10) 0.032(10) 0.064(11) -0.002(8) 0.006(8) 0.008(8) N4 0.062(18) 0.025(13) 0.067(19) 0.000 0.008(15) 0.000 N5 0.063(18) 0.023(13) 0.07(2) 0.000 0.007(17) 0.000 N6 0.07(2) 0.042(17) 0.10(3) 0.000 0.003(19) 0.000 N7 0.058(16) 0.030(13) 0.057(17) 0.000 0.021(13) 0.000 N8 0.065(18) 0.030(14) 0.057(19) 0.000 0.008(14) 0.000 N9 0.09(2) 0.052(18) 0.07(2) 0.000 0.033(17) 0.000 N10 0.028(9) 0.014(8) 0.066(11) -0.004(6) 0.006(7) -0.007(6) N11 0.031(9) 0.021(8) 0.066(11) 0.003(7) 0.003(7) -0.004(7) N12 0.023(8) 0.015(7) 0.059(10) -0.001(6) 0.004(7) -0.004(6) N13 0.08(2) 0.025(13) 0.07(2) 0.000 -0.008(17) 0.000 N14 0.068(19) 0.025(14) 0.08(2) 0.000 -0.002(18) 0.000 N15 0.09(2) 0.012(12) 0.08(2) 0.000 0.012(16) 0.000 N16 0.036(14) 0.025(12) 0.068(17) 0.000 0.001(12) 0.000 N17 0.048(16) 0.029(13) 0.069(19) 0.000 0.006(14) 0.000 N18 0.06(2) 0.07(2) 0.08(2) 0.000 -0.022(16) 0.000 O1 0.082(18) 0.050(14) 0.091(18) 0.000 0.010(13) 0.000 O2 0.09(2) 0.057(16) 0.12(2) 0.000 0.003(16) 0.000 C1 0.031(11) 0.022(10) 0.051(13) -0.004(8) 0.008(9) 0.011(7) C2 0.041(11) 0.026(9) 0.053(13) 0.000(8) 0.004(9) 0.001(8) C3 0.042(11) 0.023(9) 0.051(12) 0.000(8) 0.001(9) 0.002(8) C4 0.035(11) 0.029(11) 0.058(13) 0.003(8) 0.004(9) -0.006(9) C5 0.037(11) 0.021(9) 0.056(13) -0.001(8) 0.003(9) 0.001(8) C6 0.037(12) 0.021(10) 0.054(13) -0.002(8) -0.001(9) -0.002(8) C7 0.034(11) 0.013(9) 0.055(12) -0.004(7) 0.004(8) 0.003(8) C8 0.042(12) 0.016(9) 0.060(13) 0.002(8) 0.005(9) 0.004(9) C9 0.039(12) 0.033(12) 0.065(14) -0.007(9) 0.010(10) 0.003(9) C10 0.035(11) 0.025(10) 0.056(13) -0.005(8) 0.011(9) 0.003(9) C11 0.036(11) 0.019(10) 0.050(12) 0.000(7) 0.004(9) 0.001(8) C12 0.039(12) 0.027(10) 0.062(13) -0.006(9) 0.004(9) 0.001(9) C13 0.043(13) 0.030(11) 0.063(14) -0.003(9) 0.014(9) -0.004(10) C14 0.029(10) 0.018(9) 0.063(13) -0.003(8) 0.010(9) -0.010(7) C15 0.046(12) 0.025(9) 0.060(13) -0.004(9) 0.006(9) -0.003(8) C16 0.043(11) 0.021(9) 0.060(13) 0.002(8) 0.005(9) -0.004(8) C17 0.030(11) 0.018(10) 0.066(14) 0.001(8) 0.003(9) -0.001(8) C18 0.031(10) 0.015(9) 0.059(13) 0.004(7) 0.010(9) -0.004(8) C19 0.033(11) 0.015(9) 0.060(13) -0.002(8) 0.011(9) -0.004(8) C20 0.038(11) 0.019(9) 0.063(13) 0.005(8) 0.006(9) -0.001(8) C21 0.036(12) 0.019(9) 0.068(14) 0.007(9) -0.002(9) -0.007(9) C22 0.037(12) 0.020(9) 0.059(13) -0.004(8) 0.005(9) 0.005(9) C23 0.032(11) 0.016(9) 0.061(13) -0.002(8) 0.009(9) -0.004(8) C24 0.034(11) 0.015(10) 0.059(13) 0.005(8) 0.007(9) -0.001(8) C25 0.031(11) 0.017(9) 0.063(13) -0.003(8) 0.007(9) -0.003(8) C26 0.031(11) 0.022(10) 0.067(14) -0.008(8) 0.001(9) 0.000(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 Ag1 N2 2.255(15) . ? Ag1 N3 2.265(16) 1_455 ? Ag1 N7 2.316(16) . ? Ag1 N4 2.46(2) . ? Ag2 N12 2.241(14) 1_655 ? Ag2 N11 2.283(14) . ? Ag2 N16 2.324(16) . ? Ag2 N13 2.42(2) . ? N1 C11 1.31(2) . ? N1 C6 1.37(2) . ? N1 C1 1.41(2) . ? N2 C8 1.34(2) . ? N2 C4 1.34(2) . ? N3 C13 1.30(2) . ? N3 C9 1.38(2) . ? N3 Ag1 2.265(16) 1_655 ? N4 N5 1.08(3) . ? N4 Ag1 2.46(2) 4_575 ? N5 N6 1.19(4) . ? N7 N8 1.13(3) . ? N7 Ag1 2.316(16) 4_575 ? N8 N9 1.12(3) . ? N10 C19 1.39(2) . ? N10 C24 1.41(2) . ? N10 C14 1.42(2) . ? N11 C21 1.29(2) . ? N11 C17 1.32(2) . ? N12 C22 1.32(2) . ? N12 C26 1.32(2) . ? N12 Ag2 2.241(13) 1_455 ? N13 N14 1.03(4) . ? N13 Ag2 2.42(2) 4_575 ? N14 N15 1.27(4) . ? N16 N17 1.20(3) . ? N16 Ag2 2.324(16) 4_575 ? N17 N18 1.14(3) . ? O1 H1C 0.8501 . ? O1 H1D 0.8500 . ? O2 H2C 0.8501 . ? O2 H2D 0.8500 . ? C1 C2 1.35(2) . ? C1 C3 1.38(2) . ? C2 C2 1.37(3) 4_565 ? C2 H2 0.9300 . ? C3 C3 1.35(3) 4_565 ? C3 H3 0.9300 . ? C4 C5 1.33(3) . ? C4 H4 0.9300 . ? C5 C6 1.40(2) . ? C5 H5 0.9300 . ? C6 C7 1.41(2) . ? C7 C8 1.31(2) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.30(3) . ? C9 H9 0.9300 . ? C10 C11 1.39(2) . ? C10 H10 0.9300 . ? C11 C12 1.45(2) . ? C12 C13 1.33(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.38(2) . ? C14 C16 1.39(2) . ? C15 C15 1.35(3) 4_565 ? C15 H15 0.9300 . ? C16 C16 1.38(3) 4_565 ? C16 H16 0.9300 . ? C17 C18 1.36(2) . ? C17 H17 0.9300 . ? C18 C19 1.37(2) . ? C18 H18 0.9300 . ? C19 C20 1.37(2) . ? C20 C21 1.37(2) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.35(2) . ? C22 H22 0.9300 . ? C23 C24 1.37(2) . ? C23 H23 0.9300 . ? C24 C25 1.33(2) . ? C25 C26 1.38(2) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? 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 Ag1 N3 114.9(6) . 1_455 ? N2 Ag1 N7 135.6(7) . . ? N3 Ag1 N7 98.7(7) 1_455 . ? N2 Ag1 N4 96.4(7) . . ? N3 Ag1 N4 126.4(7) 1_455 . ? N7 Ag1 N4 85.0(7) . . ? N12 Ag2 N11 115.0(5) 1_655 . ? N12 Ag2 N16 127.9(7) 1_655 . ? N11 Ag2 N16 100.2(6) . . ? N12 Ag2 N13 105.4(7) 1_655 . ? N11 Ag2 N13 122.3(8) . . ? N16 Ag2 N13 84.1(7) . . ? C11 N1 C6 124.8(16) . . ? C11 N1 C1 117.3(15) . . ? C6 N1 C1 117.9(14) . . ? C8 N2 C4 112.2(16) . . ? C8 N2 Ag1 123.1(11) . . ? C4 N2 Ag1 121.6(13) . . ? C13 N3 C9 112.2(17) . . ? C13 N3 Ag1 118.5(13) . 1_655 ? C9 N3 Ag1 127.1(13) . 1_655 ? N5 N4 Ag1 133.6(6) . 4_575 ? N5 N4 Ag1 133.6(6) . . ? Ag1 N4 Ag1 91.1(10) 4_575 . ? N4 N5 N6 173(3) . . ? N8 N7 Ag1 129.3(7) . . ? N8 N7 Ag1 129.3(7) . 4_575 ? Ag1 N7 Ag1 98.5(9) . 4_575 ? N9 N8 N7 179(4) . . ? C19 N10 C24 123.8(15) . . ? C19 N10 C14 119.5(14) . . ? C24 N10 C14 116.6(13) . . ? C21 N11 C17 115.1(16) . . ? C21 N11 Ag2 117.6(12) . . ? C17 N11 Ag2 125.3(12) . . ? C22 N12 C26 115.3(15) . . ? C22 N12 Ag2 121.1(11) . 1_455 ? C26 N12 Ag2 122.3(12) . 1_455 ? N14 N13 Ag2 131.1(10) . . ? N14 N13 Ag2 131.1(10) . 4_575 ? Ag2 N13 Ag2 92.9(11) . 4_575 ? N13 N14 N15 177(4) . . ? N17 N16 Ag2 126.7(8) . 4_575 ? N17 N16 Ag2 126.7(8) . . ? Ag2 N16 Ag2 97.7(9) 4_575 . ? N18 N17 N16 177(3) . . ? H1C O1 H1D 108.5 . . ? H2C O2 H2D 108.5 . . ? C2 C1 C3 118.9(18) . . ? C2 C1 N1 120.3(16) . . ? C3 C1 N1 120.7(16) . . ? C1 C2 C2 120.7(11) . 4_565 ? C1 C2 H2 119.6 . . ? C2 C2 H2 119.6 4_565 . ? C3 C3 C1 120.3(11) 4_565 . ? C3 C3 H3 119.8 4_565 . ? C1 C3 H3 119.8 . . ? C5 C4 N2 126.8(19) . . ? C5 C4 H4 116.6 . . ? N2 C4 H4 116.6 . . ? C4 C5 C6 119.4(18) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? N1 C6 C5 122.1(16) . . ? N1 C6 C7 123.9(17) . . ? C5 C6 C7 113.3(17) . . ? C8 C7 C6 121.4(18) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 N2 125.7(17) . . ? C7 C8 H8 117.2 . . ? N2 C8 H8 117.2 . . ? C10 C9 N3 128.1(19) . . ? C10 C9 H9 115.9 . . ? N3 C9 H9 115.9 . . ? C9 C10 C11 120.3(19) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? N1 C11 C10 123.2(17) . . ? N1 C11 C12 124.8(17) . . ? C10 C11 C12 111.7(17) . . ? C13 C12 C11 122.0(19) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? N3 C13 C12 125(2) . . ? N3 C13 H13 117.4 . . ? C12 C13 H13 117.4 . . ? C15 C14 C16 120.5(17) . . ? C15 C14 N10 120.6(16) . . ? C16 C14 N10 118.6(16) . . ? C15 C15 C14 120.2(11) 4_565 . ? C15 C15 H15 119.9 4_565 . ? C14 C15 H15 119.9 . . ? C16 C16 C14 119.2(10) 4_565 . ? C16 C16 H16 120.4 4_565 . ? C14 C16 H16 120.4 . . ? N11 C17 C18 125.5(17) . . ? N11 C17 H17 117.3 . . ? C18 C17 H17 117.3 . . ? C17 C18 C19 117.9(17) . . ? C17 C18 H18 121.0 . . ? C19 C18 H18 121.0 . . ? C20 C19 C18 117.4(17) . . ? C20 C19 N10 122.5(17) . . ? C18 C19 N10 119.9(16) . . ? C21 C20 C19 118.6(18) . . ? C21 C20 H20 120.7 . . ? C19 C20 H20 120.7 . . ? N11 C21 C20 125.3(18) . . ? N11 C21 H21 117.4 . . ? C20 C21 H21 117.4 . . ? N12 C22 C23 121.9(17) . . ? N12 C22 H22 119.1 . . ? C23 C22 H22 119.1 . . ? C22 C23 C24 122.1(17) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C25 C24 C23 116.6(17) . . ? C25 C24 N10 119.7(16) . . ? C23 C24 N10 122.7(16) . . ? C24 C25 C26 117.7(17) . . ? C24 C25 H25 121.1 . . ? C26 C25 H25 121.1 . . ? N12 C26 C25 125.8(17) . . ? N12 C26 H26 117.1 . . ? C25 C26 H26 117.1 . . ? 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 N3 Ag1 N2 C8 167.5(14) 1_455 . . . ? N7 Ag1 N2 C8 -57.1(17) . . . . ? N4 Ag1 N2 C8 32.2(15) . . . . ? N3 Ag1 N2 C4 -33.9(15) 1_455 . . . ? N7 Ag1 N2 C4 101.5(15) . . . . ? N4 Ag1 N2 C4 -169.2(15) . . . . ? N2 Ag1 N4 N5 63(3) . . . . ? N3 Ag1 N4 N5 -64(3) 1_455 . . . ? N7 Ag1 N4 N5 -161(3) . . . . ? N2 Ag1 N4 Ag1 -130.3(7) . . . 4_575 ? N3 Ag1 N4 Ag1 102.2(8) 1_455 . . 4_575 ? N7 Ag1 N4 Ag1 5.1(8) . . . 4_575 ? Ag1 N4 N5 N6 -81(3) 4_575 . . . ? Ag1 N4 N5 N6 81(3) . . . . ? N2 Ag1 N7 N8 -110(3) . . . . ? N3 Ag1 N7 N8 30(3) 1_455 . . . ? N4 Ag1 N7 N8 156(3) . . . . ? N2 Ag1 N7 Ag1 88.5(11) . . . 4_575 ? N3 Ag1 N7 Ag1 -131.6(8) 1_455 . . 4_575 ? N4 Ag1 N7 Ag1 -5.4(9) . . . 4_575 ? Ag1 N7 N8 N9 -78(3) . . . . ? Ag1 N7 N8 N9 78(2) 4_575 . . . ? N12 Ag2 N11 C21 -176.0(14) 1_655 . . . ? N16 Ag2 N11 C21 -35.4(16) . . . . ? N13 Ag2 N11 C21 54.0(17) . . . . ? N12 Ag2 N11 C17 21.0(17) 1_655 . . . ? N16 Ag2 N11 C17 161.6(15) . . . . ? N13 Ag2 N11 C17 -109.0(16) . . . . ? N12 Ag2 N13 N14 -84(4) 1_655 . . . ? N11 Ag2 N13 N14 50(4) . . . . ? N16 Ag2 N13 N14 148(4) . . . . ? N12 Ag2 N13 Ag2 119.7(8) 1_655 . . 4_575 ? N11 Ag2 N13 Ag2 -106.4(9) . . . 4_575 ? N16 Ag2 N13 Ag2 -8.0(9) . . . 4_575 ? Ag2 N13 N14 N15 -74(3) . . . . ? Ag2 N13 N14 N15 74(3) 4_575 . . . ? N12 Ag2 N16 N17 115(2) 1_655 . . . ? N11 Ag2 N16 N17 -18(2) . . . . ? N13 Ag2 N16 N17 -140(2) . . . . ? N12 Ag2 N16 Ag2 -96.6(8) 1_655 . . 4_575 ? N11 Ag2 N16 Ag2 130.2(7) . . . 4_575 ? N13 Ag2 N16 Ag2 8.4(9) . . . 4_575 ? Ag2 N16 N17 N18 -70.0(17) 4_575 . . . ? Ag2 N16 N17 N18 70.0(17) . . . . ? C11 N1 C1 C2 79(2) . . . . ? C6 N1 C1 C2 -99.4(19) . . . . ? C11 N1 C1 C3 -104.1(19) . . . . ? C6 N1 C1 C3 77(2) . . . . ? C3 C1 C2 C2 3.6(19) . . . 4_565 ? N1 C1 C2 C2 -179.7(10) . . . 4_565 ? C2 C1 C3 C3 -3.6(19) . . . 4_565 ? N1 C1 C3 C3 179.7(10) . . . 4_565 ? C8 N2 C4 C5 -6(3) . . . . ? Ag1 N2 C4 C5 -167.0(15) . . . . ? N2 C4 C5 C6 12(3) . . . . ? C11 N1 C6 C5 -160.2(17) . . . . ? C1 N1 C6 C5 18(2) . . . . ? C11 N1 C6 C7 30(3) . . . . ? C1 N1 C6 C7 -151.2(17) . . . . ? C4 C5 C6 N1 177.2(16) . . . . ? C4 C5 C6 C7 -12(3) . . . . ? N1 C6 C7 C8 178.3(17) . . . . ? C5 C6 C7 C8 8(3) . . . . ? C6 C7 C8 N2 -3(3) . . . . ? C4 N2 C8 C7 1(3) . . . . ? Ag1 N2 C8 C7 161.5(15) . . . . ? C13 N3 C9 C10 -4(3) . . . . ? Ag1 N3 C9 C10 -166.3(16) 1_655 . . . ? N3 C9 C10 C11 5(3) . . . . ? C6 N1 C11 C10 -165.8(17) . . . . ? C1 N1 C11 C10 16(3) . . . . ? C6 N1 C11 C12 21(3) . . . . ? C1 N1 C11 C12 -157.7(17) . . . . ? C9 C10 C11 N1 -179.9(18) . . . . ? C9 C10 C11 C12 -6(3) . . . . ? N1 C11 C12 C13 -178.6(18) . . . . ? C10 C11 C12 C13 7(3) . . . . ? C9 N3 C13 C12 5(3) . . . . ? Ag1 N3 C13 C12 169.4(16) 1_655 . . . ? C11 C12 C13 N3 -8(3) . . . . ? C19 N10 C14 C15 102(2) . . . . ? C24 N10 C14 C15 -82(2) . . . . ? C19 N10 C14 C16 -71(2) . . . . ? C24 N10 C14 C16 104.4(19) . . . . ? C16 C14 C15 C15 -4(2) . . . 4_565 ? N10 C14 C15 C15 -177.4(10) . . . 4_565 ? C15 C14 C16 C16 4(2) . . . 4_565 ? N10 C14 C16 C16 177.5(10) . . . 4_565 ? C21 N11 C17 C18 -2(3) . . . . ? Ag2 N11 C17 C18 161.8(14) . . . . ? N11 C17 C18 C19 -1(3) . . . . ? C17 C18 C19 C20 5(3) . . . . ? C17 C18 C19 N10 180.0(15) . . . . ? C24 N10 C19 C20 -15(3) . . . . ? C14 N10 C19 C20 160.2(18) . . . . ? C24 N10 C19 C18 169.4(16) . . . . ? C14 N10 C19 C18 -15(2) . . . . ? C18 C19 C20 C21 -5(3) . . . . ? N10 C19 C20 C21 179.9(17) . . . . ? C17 N11 C21 C20 1(3) . . . . ? Ag2 N11 C21 C20 -163.4(15) . . . . ? C19 C20 C21 N11 2(3) . . . . ? C26 N12 C22 C23 0(3) . . . . ? Ag2 N12 C22 C23 -167.6(13) 1_455 . . . ? N12 C22 C23 C24 5(3) . . . . ? C22 C23 C24 C25 -9(3) . . . . ? C22 C23 C24 N10 -177.3(17) . . . . ? C19 N10 C24 C25 156.9(17) . . . . ? C14 N10 C24 C25 -19(2) . . . . ? C19 N10 C24 C23 -35(3) . . . . ? C14 N10 C24 C23 149.6(17) . . . . ? C23 C24 C25 C26 8(3) . . . . ? N10 C24 C25 C26 176.9(15) . . . . ? C22 N12 C26 C25 0(3) . . . . ? Ag2 N12 C26 C25 166.9(14) 1_455 . . . ? C24 C25 C26 N12 -4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 24.15 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 3.780 _refine_diff_density_min -1.530 _refine_diff_density_rms 0.323 _database_code_depnum_ccdc_archive 'CCDC 939484' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110403b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C60 H73 Co4 N10 O30 S4' _chemical_formula_weight 1778.24 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' Co Co 0.3494 0.9721 '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 12.2383(11) _cell_length_b 12.2768(12) _cell_length_c 14.7929(16) _cell_angle_alpha 109.411(2) _cell_angle_beta 108.631(2) _cell_angle_gamma 98.7100(10) _cell_volume 1902.1(3) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2168 _cell_measurement_theta_min 2.865 _cell_measurement_theta_max 27.223 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 915 _exptl_absorpt_coefficient_mu 1.055 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6899 _exptl_absorpt_correction_T_max 0.8838 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 '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 9889 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6603 _reflns_number_gt 3706 _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^)+(0.1076P)^2^+2.4634P] 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 6603 _refine_ls_number_parameters 550 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1136 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.2136 _refine_ls_wR_factor_gt 0.1737 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.034 _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 Co1 Co 1.0000 1.0000 0.5000 0.0199(3) Uani 1 2 d S . . Co2 Co 0.0000 0.5000 0.0000 0.0201(3) Uani 1 2 d S . . Co3 Co 0.0000 0.0000 0.0000 0.0207(3) Uani 1 2 d S . . Co4 Co 1.0000 0.5000 0.5000 0.0211(3) Uani 1 2 d S . . N1 N 0.8330(5) 0.9418(5) 0.3661(4) 0.0276(13) Uani 1 1 d . . . N2 N 0.1705(5) 0.6187(5) 0.0402(4) 0.0252(12) Uani 1 1 d . . . N3 N 0.1681(4) 0.0539(5) 0.1255(4) 0.0234(12) Uani 1 1 d . . . N4 N 0.8239(5) 0.3917(5) 0.4659(4) 0.0258(13) Uani 1 1 d . . . N5 N 0.508(3) 0.590(3) 0.324(2) 0.159(13) Uani 0.50 1 d P . . N6 N 0.5843(19) 0.5550(17) 0.9957(18) 0.095(7) Uani 0.50 1 d P . . O1 O 1.1018(4) 1.0096(4) 0.4107(3) 0.0299(11) Uani 1 1 d . . . H1B H 1.0789 1.0513 0.3765 0.036 Uiso 1 1 d R . . H1C H 1.0933 0.9393 0.3679 0.036 Uiso 1 1 d R . . O2 O 0.9981(4) 0.8198(4) 0.4681(3) 0.0329(12) Uani 1 1 d . . . H2C H 0.9728 0.7740 0.4037 0.039 Uiso 1 1 d R . . H2D H 0.9896 0.7762 0.5010 0.039 Uiso 1 1 d R . . O3 O 0.0910(4) 0.3813(4) 0.0542(4) 0.0365(12) Uani 1 1 d . . . H3B H 0.0979 0.3296 0.0030 0.044 Uiso 1 1 d R . . H3C H 0.0476 0.3436 0.0753 0.044 Uiso 1 1 d R . . O4 O 0.0094(4) 0.5893(4) 0.1486(3) 0.0303(11) Uani 1 1 d . . . O5 O 0.0935(5) 0.7960(5) 0.2713(4) 0.0542(16) Uani 1 1 d . . . O6 O -0.0969(5) 0.7355(5) 0.1284(4) 0.0446(14) Uani 1 1 d . . . O7 O -0.0826(5) 0.6692(4) 0.2661(4) 0.0376(12) Uani 1 1 d . . . O8 O -0.0228(4) 0.1720(4) 0.0613(4) 0.0319(11) Uani 1 1 d . . . H8A H -0.0102 0.1938 0.1333 0.038 Uiso 1 1 d R . . H8B H -0.1029 0.1707 0.0225 0.038 Uiso 1 1 d R . . O9 O -0.0821(4) -0.0452(4) 0.0999(4) 0.0357(12) Uani 1 1 d . . . H9B H -0.0430 0.0042 0.1633 0.043 Uiso 1 1 d R . . H9C H -0.0823 -0.1160 0.0955 0.043 Uiso 1 1 d R . . O10 O 0.9319(4) 0.4974(4) 0.3461(3) 0.0343(12) Uani 1 1 d . . . H10B H 0.9596 0.4533 0.3064 0.041 Uiso 1 1 d R . . H10C H 0.9469 0.5679 0.3474 0.041 Uiso 1 1 d R . . O11 O 1.0323(4) 0.3307(4) 0.4303(3) 0.0308(11) Uani 1 1 d . A . O12 O 0.9791(14) 0.3003(9) 0.2506(6) 0.060(5) Uani 0.82(3) 1 d P A 1 O13 O 1.1851(9) 0.3473(8) 0.3607(9) 0.079(5) Uani 0.82(3) 1 d P A 1 O14 O 1.0498(15) 0.1520(14) 0.3057(13) 0.046(4) Uani 0.82(3) 1 d P A 1 O12' O 1.219(4) 0.296(4) 0.412(3) 0.072(17) Uani 0.18(3) 1 d P A 2 O13' O 1.023(7) 0.158(7) 0.300(7) 0.053(18) Uani 0.18(3) 1 d PU A 2 O14' O 1.080(4) 0.348(3) 0.290(3) 0.048(14) Uani 0.18(3) 1 d P A 2 O15 O 0.2646(8) 0.4627(7) 0.2446(6) 0.114(3) Uani 1 1 d . . . H15B H 0.2087 0.4369 0.1842 0.136 Uiso 1 1 d R . . H15C H 0.2412 0.4284 0.2793 0.136 Uiso 0.50 1 d PR . . S1 S -0.01845(17) 0.69926(16) 0.20409(14) 0.0304(4) Uani 1 1 d . . . S2 S 1.0649(2) 0.28190(17) 0.33836(16) 0.0415(5) Uani 1 1 d . . . C1 C 0.5044(5) 0.8523(5) 0.1113(5) 0.0178(13) Uani 1 1 d . . . C2 C 0.4999(6) 0.9254(6) 0.0521(5) 0.0235(14) Uani 1 1 d . . . C3 C 0.4221(6) 0.9960(6) 0.0495(5) 0.0267(15) Uani 1 1 d . . . H3 H 0.3691 0.9925 0.0823 0.032 Uiso 1 1 calc R . . C4 C 0.4228(6) 1.0718(6) -0.0019(5) 0.0294(16) Uani 1 1 d . . . H4 H 0.3716 1.1205 -0.0026 0.035 Uiso 1 1 calc R . . C5 C 0.8054(6) 1.0173(6) 0.3192(5) 0.0324(17) Uani 1 1 d . . . H5 H 0.8620 1.0912 0.3439 0.039 Uiso 1 1 calc R . . C6 C 0.6995(6) 0.9912(6) 0.2377(5) 0.0317(16) Uani 1 1 d . . . H6 H 0.6849 1.0473 0.2093 0.038 Uiso 1 1 calc R . . C7 C 0.6135(6) 0.8814(6) 0.1971(5) 0.0238(15) Uani 1 1 d . . . C8 C 0.6418(6) 0.8022(6) 0.2443(5) 0.0269(15) Uani 1 1 d . . . H8 H 0.5879 0.7267 0.2202 0.032 Uiso 1 1 calc R . . C9 C 0.7498(6) 0.8372(6) 0.3265(5) 0.0294(16) Uani 1 1 d . . . H9 H 0.7663 0.7833 0.3570 0.035 Uiso 1 1 calc R . . C10 C 0.2558(6) 0.6699(6) 0.1375(5) 0.0280(15) Uani 1 1 d . . . H10 H 0.2386 0.6540 0.1895 0.034 Uiso 1 1 calc R . . C11 C 0.3673(6) 0.7445(6) 0.1646(5) 0.0269(15) Uani 1 1 d . . . H11 H 0.4238 0.7768 0.2332 0.032 Uiso 1 1 calc R . . C12 C 0.3951(6) 0.7714(6) 0.0890(5) 0.0252(15) Uani 1 1 d . . . C13 C 0.3070(6) 0.7191(6) -0.0117(5) 0.0310(16) Uani 1 1 d . . . H13 H 0.3214 0.7352 -0.0646 0.037 Uiso 1 1 calc R . . C14 C 0.1986(6) 0.6437(6) -0.0334(5) 0.0289(16) Uani 1 1 d . . . H14 H 0.1417 0.6081 -0.1018 0.035 Uiso 1 1 calc R . . C15 C 0.4916(5) 0.1472(5) 0.3877(4) 0.0165(13) Uani 1 1 d . . . C16 C 0.4971(6) 0.0749(6) 0.4471(5) 0.0257(15) Uani 1 1 d . . . C17 C 0.5806(6) 0.0093(6) 0.4538(5) 0.0291(16) Uani 1 1 d . . . H17 H 0.6349 0.0161 0.4227 0.035 Uiso 1 1 calc R . . C18 C 0.5840(6) -0.0655(6) 0.5059(5) 0.0294(16) Uani 1 1 d . . . H18 H 0.6398 -0.1092 0.5097 0.035 Uiso 1 1 calc R . . C19 C 0.2502(6) 0.1620(6) 0.1698(5) 0.0278(16) Uani 1 1 d . . . H19 H 0.2337 0.2168 0.1402 0.033 Uiso 1 1 calc R . . C20 C 0.3570(6) 0.1988(6) 0.2556(5) 0.0271(15) Uani 1 1 d . . . H20 H 0.4094 0.2757 0.2828 0.033 Uiso 1 1 calc R . . C21 C 0.3844(6) 0.1179(6) 0.3006(5) 0.0241(15) Uani 1 1 d . . . C22 C 0.2993(6) 0.0057(6) 0.2587(5) 0.0253(15) Uani 1 1 d . . . H22 H 0.3128 -0.0496 0.2882 0.030 Uiso 1 1 calc R . . C23 C 0.1955(6) -0.0219(6) 0.1733(5) 0.0253(15) Uani 1 1 d . . . H23 H 0.1402 -0.0973 0.1464 0.030 Uiso 1 1 calc R . . C24 C 0.7407(6) 0.3366(6) 0.3680(6) 0.0340(17) Uani 1 1 d . . . H24 H 0.7590 0.3520 0.3162 0.041 Uiso 1 1 calc R . . C25 C 0.6302(6) 0.2588(6) 0.3386(5) 0.0348(17) Uani 1 1 d . . . H25 H 0.5757 0.2241 0.2692 0.042 Uiso 1 1 calc R . . C26 C 0.6008(6) 0.2328(6) 0.4135(5) 0.0253(15) Uani 1 1 d . . . C27 C 0.6846(6) 0.2878(6) 0.5133(5) 0.0337(17) Uani 1 1 d . . . H27 H 0.6686 0.2729 0.5661 0.040 Uiso 1 1 calc R . . C28 C 0.7926(6) 0.3652(6) 0.5364(5) 0.0331(17) Uani 1 1 d . . . H28 H 0.8475 0.4015 0.6056 0.040 Uiso 1 1 calc R . . C29 C 0.543(4) 0.567(3) 0.395(4) 0.160(15) Uani 0.50 1 d P . . C30 C 0.563(4) 0.565(4) 0.499(3) 0.172(15) Uani 0.50 1 d P . . H30A H 0.5600 0.6399 0.5453 0.257 Uiso 0.50 1 calc PR . . H30B H 0.6404 0.5534 0.5282 0.257 Uiso 0.50 1 calc PR . . H30C H 0.5014 0.4998 0.4918 0.257 Uiso 0.50 1 calc PR . . C31 C 0.485(3) 0.525(2) 0.9364(17) 0.083(8) Uani 0.50 1 d P . . C32 C 0.398(3) 0.527(3) 0.838(2) 0.157(15) Uani 0.50 1 d P . . H32A H 0.3616 0.5905 0.8559 0.236 Uiso 0.50 1 calc PR . . H32B H 0.3369 0.4511 0.7981 0.236 Uiso 0.50 1 calc PR . . H32C H 0.4413 0.5411 0.7967 0.236 Uiso 0.50 1 calc PR . . 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 Co1 0.0215(7) 0.0204(7) 0.0165(6) 0.0078(5) 0.0053(5) 0.0063(5) Co2 0.0223(7) 0.0161(6) 0.0197(7) 0.0054(5) 0.0087(5) 0.0029(5) Co3 0.0200(7) 0.0205(7) 0.0194(7) 0.0085(5) 0.0048(5) 0.0054(5) Co4 0.0211(7) 0.0204(7) 0.0194(7) 0.0079(5) 0.0071(5) 0.0024(5) N1 0.026(3) 0.028(3) 0.024(3) 0.012(3) 0.004(3) 0.003(3) N2 0.025(3) 0.023(3) 0.025(3) 0.011(3) 0.009(3) 0.002(2) N3 0.019(3) 0.026(3) 0.024(3) 0.011(3) 0.006(2) 0.006(2) N4 0.025(3) 0.025(3) 0.026(3) 0.013(3) 0.008(3) 0.003(2) N5 0.17(3) 0.19(3) 0.11(2) 0.08(2) 0.05(2) -0.01(2) N6 0.090(16) 0.076(13) 0.097(16) 0.005(12) 0.027(13) 0.054(12) O1 0.041(3) 0.026(3) 0.031(3) 0.014(2) 0.021(2) 0.013(2) O2 0.056(3) 0.020(2) 0.020(2) 0.008(2) 0.012(2) 0.010(2) O3 0.055(3) 0.025(3) 0.032(3) 0.014(2) 0.020(3) 0.011(2) O4 0.040(3) 0.024(3) 0.025(3) 0.007(2) 0.015(2) 0.009(2) O5 0.058(4) 0.029(3) 0.054(4) -0.002(3) 0.022(3) 0.000(3) O6 0.072(4) 0.045(3) 0.033(3) 0.021(3) 0.028(3) 0.032(3) O7 0.053(3) 0.037(3) 0.035(3) 0.017(2) 0.028(3) 0.017(2) O8 0.042(3) 0.026(3) 0.026(3) 0.008(2) 0.013(2) 0.012(2) O9 0.047(3) 0.034(3) 0.031(3) 0.017(2) 0.018(2) 0.012(2) O10 0.044(3) 0.029(3) 0.029(3) 0.012(2) 0.015(2) 0.007(2) O11 0.047(3) 0.026(3) 0.029(3) 0.014(2) 0.022(2) 0.016(2) O12 0.114(12) 0.059(6) 0.030(5) 0.026(4) 0.035(6) 0.055(7) O13 0.081(8) 0.060(6) 0.094(10) 0.014(6) 0.060(8) 0.001(5) O14 0.075(9) 0.033(5) 0.046(6) 0.021(4) 0.029(6) 0.032(6) O12' 0.09(3) 0.08(3) 0.06(3) 0.02(2) 0.05(2) 0.02(2) O13' 0.07(2) 0.04(2) 0.05(2) 0.006(11) 0.056(14) 0.004(10) O14' 0.06(4) 0.05(2) 0.06(2) 0.031(19) 0.03(3) 0.01(2) O15 0.137(8) 0.082(6) 0.073(5) 0.027(5) -0.005(5) 0.012(5) S1 0.0469(11) 0.0237(9) 0.0253(9) 0.0093(8) 0.0205(9) 0.0106(8) S2 0.0692(15) 0.0284(11) 0.0424(12) 0.0145(9) 0.0405(12) 0.0155(10) C1 0.012(3) 0.022(3) 0.021(3) 0.017(3) 0.003(3) -0.001(3) C2 0.021(4) 0.027(4) 0.020(3) 0.014(3) 0.004(3) -0.001(3) C3 0.026(4) 0.034(4) 0.023(4) 0.015(3) 0.012(3) 0.003(3) C4 0.027(4) 0.035(4) 0.032(4) 0.019(3) 0.011(3) 0.013(3) C5 0.027(4) 0.031(4) 0.032(4) 0.017(3) 0.004(3) -0.003(3) C6 0.032(4) 0.033(4) 0.030(4) 0.021(3) 0.006(3) 0.002(3) C7 0.021(4) 0.027(4) 0.024(4) 0.014(3) 0.006(3) 0.005(3) C8 0.024(4) 0.025(4) 0.031(4) 0.016(3) 0.006(3) 0.006(3) C9 0.032(4) 0.028(4) 0.030(4) 0.016(3) 0.008(3) 0.012(3) C10 0.030(4) 0.028(4) 0.029(4) 0.015(3) 0.012(3) 0.008(3) C11 0.024(4) 0.032(4) 0.023(4) 0.013(3) 0.006(3) 0.006(3) C12 0.024(4) 0.025(4) 0.027(4) 0.014(3) 0.008(3) 0.002(3) C13 0.028(4) 0.035(4) 0.026(4) 0.014(3) 0.009(3) -0.002(3) C14 0.026(4) 0.030(4) 0.025(4) 0.013(3) 0.005(3) 0.001(3) C15 0.008(3) 0.028(4) 0.014(3) 0.016(3) -0.002(2) 0.002(3) C16 0.025(4) 0.029(4) 0.020(3) 0.013(3) 0.003(3) 0.004(3) C17 0.027(4) 0.036(4) 0.029(4) 0.018(3) 0.012(3) 0.006(3) C18 0.024(4) 0.034(4) 0.031(4) 0.015(3) 0.010(3) 0.007(3) C19 0.030(4) 0.026(4) 0.029(4) 0.016(3) 0.008(3) 0.010(3) C20 0.025(4) 0.025(4) 0.029(4) 0.015(3) 0.006(3) 0.004(3) C21 0.020(4) 0.028(4) 0.024(4) 0.013(3) 0.007(3) 0.006(3) C22 0.020(4) 0.027(4) 0.028(4) 0.015(3) 0.005(3) 0.008(3) C23 0.026(4) 0.025(4) 0.022(4) 0.012(3) 0.004(3) 0.004(3) C24 0.029(4) 0.040(4) 0.031(4) 0.020(4) 0.008(3) 0.001(3) C25 0.027(4) 0.043(5) 0.027(4) 0.017(4) 0.002(3) -0.001(3) C26 0.021(4) 0.030(4) 0.026(4) 0.014(3) 0.008(3) 0.005(3) C27 0.032(4) 0.040(4) 0.024(4) 0.016(3) 0.008(3) -0.001(3) C28 0.028(4) 0.038(4) 0.025(4) 0.012(3) 0.006(3) -0.002(3) C29 0.18(4) 0.15(3) 0.14(4) 0.07(3) 0.03(3) 0.06(3) C30 0.18(4) 0.17(4) 0.16(4) 0.07(3) 0.05(3) 0.07(3) C31 0.11(2) 0.074(15) 0.055(14) 0.013(12) 0.020(15) 0.068(16) C32 0.13(3) 0.10(2) 0.16(3) -0.03(2) 0.03(2) 0.08(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 Co1 O2 2.098(4) . ? Co1 O2 2.098(4) 2_776 ? Co1 O1 2.103(4) 2_776 ? Co1 O1 2.103(4) . ? Co1 N1 2.155(5) . ? Co1 N1 2.155(5) 2_776 ? Co2 O4 2.060(4) . ? Co2 O4 2.060(4) 2_565 ? Co2 N2 2.132(5) 2_565 ? Co2 N2 2.132(5) . ? Co2 O3 2.169(4) . ? Co2 O3 2.169(4) 2_565 ? Co3 O8 2.103(4) 2 ? Co3 O8 2.103(4) . ? Co3 N3 2.109(5) 2 ? Co3 N3 2.109(5) . ? Co3 O9 2.198(4) . ? Co3 O9 2.198(4) 2 ? Co4 O10 2.147(4) 2_766 ? Co4 O10 2.147(4) . ? Co4 O11 2.150(4) 2_766 ? Co4 O11 2.150(4) . ? Co4 N4 2.158(5) . ? Co4 N4 2.158(5) 2_766 ? N1 C9 1.324(8) . ? N1 C5 1.351(8) . ? N2 C10 1.341(8) . ? N2 C14 1.350(8) . ? N3 C19 1.340(8) . ? N3 C23 1.365(8) . ? N4 C28 1.336(8) . ? N4 C24 1.338(8) . ? N5 C29 1.14(4) . ? N6 C31 1.16(3) . ? N6 C31 1.91(3) 2_667 ? O1 H1B 0.8498 . ? O1 H1C 0.8500 . ? O2 H2C 0.8500 . ? O2 H2D 0.8500 . ? O3 H3B 0.8500 . ? O3 H3C 0.8499 . ? O4 S1 1.481(4) . ? O5 S1 1.459(6) . ? O6 S1 1.465(5) . ? O7 S1 1.480(5) . ? O8 H8A 0.9600 . ? O8 H8B 0.9600 . ? O9 H9B 0.8500 . ? O9 H9C 0.8499 . ? O10 H10B 0.8501 . ? O10 H10C 0.8500 . ? O11 S2 1.499(4) . ? O12 S2 1.495(9) . ? O13 S2 1.440(9) . ? O14 S2 1.467(15) . ? O12' S2 1.80(5) . ? O13' S2 1.38(8) . ? O14' S2 1.27(3) . ? O15 H15B 0.8500 . ? O15 H15C 0.8500 . ? C1 C12 1.407(8) . ? C1 C7 1.412(8) . ? C1 C2 1.442(8) . ? C2 C4 1.379(9) 2_675 ? C2 C3 1.381(9) . ? C3 C4 1.385(9) . ? C3 H3 0.9300 . ? C4 C2 1.379(9) 2_675 ? C4 H4 0.9300 . ? C5 C6 1.362(9) . ? C5 H5 0.9300 . ? C6 C7 1.384(9) . ? C6 H6 0.9300 . ? C7 C8 1.398(8) . ? C8 C9 1.364(9) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.374(9) . ? C10 H10 0.9300 . ? C11 C12 1.391(9) . ? C11 H11 0.9300 . ? C12 C13 1.386(9) . ? C13 C14 1.371(9) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C21 1.408(8) . ? C15 C26 1.420(8) . ? C15 C16 1.436(8) . ? C16 C17 1.392(9) . ? C16 C18 1.393(9) 2_656 ? C17 C18 1.379(9) . ? C17 H17 0.9300 . ? C18 C16 1.393(9) 2_656 ? C18 H18 0.9300 . ? C19 C20 1.380(9) . ? C19 H19 0.9300 . ? C20 C21 1.393(9) . ? C20 H20 0.9300 . ? C21 C22 1.397(9) . ? C22 C23 1.372(9) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.374(9) . ? C24 H24 0.9300 . ? C25 C26 1.384(9) . ? C25 H25 0.9300 . ? C26 C27 1.359(9) . ? C27 C28 1.372(9) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C30 1.49(5) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 C32 1.52(4) . ? C31 N6 1.91(3) 2_667 ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 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 O2 Co1 O2 180.000(1) . 2_776 ? O2 Co1 O1 89.71(17) . 2_776 ? O2 Co1 O1 90.29(17) 2_776 2_776 ? O2 Co1 O1 90.29(17) . . ? O2 Co1 O1 89.71(17) 2_776 . ? O1 Co1 O1 180.000(1) 2_776 . ? O2 Co1 N1 90.22(19) . . ? O2 Co1 N1 89.78(19) 2_776 . ? O1 Co1 N1 88.08(19) 2_776 . ? O1 Co1 N1 91.92(19) . . ? O2 Co1 N1 89.78(19) . 2_776 ? O2 Co1 N1 90.22(19) 2_776 2_776 ? O1 Co1 N1 91.92(19) 2_776 2_776 ? O1 Co1 N1 88.08(19) . 2_776 ? N1 Co1 N1 180.000(1) . 2_776 ? O4 Co2 O4 180.00(14) . 2_565 ? O4 Co2 N2 90.07(19) . 2_565 ? O4 Co2 N2 89.93(19) 2_565 2_565 ? O4 Co2 N2 89.93(19) . . ? O4 Co2 N2 90.07(19) 2_565 . ? N2 Co2 N2 180.0 2_565 . ? O4 Co2 O3 88.78(17) . . ? O4 Co2 O3 91.22(17) 2_565 . ? N2 Co2 O3 90.55(19) 2_565 . ? N2 Co2 O3 89.45(19) . . ? O4 Co2 O3 91.22(17) . 2_565 ? O4 Co2 O3 88.78(17) 2_565 2_565 ? N2 Co2 O3 89.45(19) 2_565 2_565 ? N2 Co2 O3 90.55(19) . 2_565 ? O3 Co2 O3 180.0 . 2_565 ? O8 Co3 O8 180.0(3) 2 . ? O8 Co3 N3 90.70(19) 2 2 ? O8 Co3 N3 89.30(19) . 2 ? O8 Co3 N3 89.30(19) 2 . ? O8 Co3 N3 90.70(19) . . ? N3 Co3 N3 180.0(4) 2 . ? O8 Co3 O9 93.73(17) 2 . ? O8 Co3 O9 86.27(17) . . ? N3 Co3 O9 92.75(18) 2 . ? N3 Co3 O9 87.25(18) . . ? O8 Co3 O9 86.27(17) 2 2 ? O8 Co3 O9 93.73(17) . 2 ? N3 Co3 O9 87.25(18) 2 2 ? N3 Co3 O9 92.75(18) . 2 ? O9 Co3 O9 180.0(4) . 2 ? O10 Co4 O10 180.000(1) 2_766 . ? O10 Co4 O11 86.85(17) 2_766 2_766 ? O10 Co4 O11 93.15(17) . 2_766 ? O10 Co4 O11 93.15(17) 2_766 . ? O10 Co4 O11 86.85(17) . . ? O11 Co4 O11 180.000(1) 2_766 . ? O10 Co4 N4 91.18(18) 2_766 . ? O10 Co4 N4 88.82(18) . . ? O11 Co4 N4 94.76(19) 2_766 . ? O11 Co4 N4 85.24(19) . . ? O10 Co4 N4 88.82(18) 2_766 2_766 ? O10 Co4 N4 91.18(18) . 2_766 ? O11 Co4 N4 85.24(19) 2_766 2_766 ? O11 Co4 N4 94.76(19) . 2_766 ? N4 Co4 N4 180.0 . 2_766 ? C9 N1 C5 115.4(6) . . ? C9 N1 Co1 125.1(4) . . ? C5 N1 Co1 119.5(4) . . ? C10 N2 C14 116.6(6) . . ? C10 N2 Co2 122.6(4) . . ? C14 N2 Co2 120.7(4) . . ? C19 N3 C23 114.8(5) . . ? C19 N3 Co3 125.9(4) . . ? C23 N3 Co3 119.1(4) . . ? C28 N4 C24 114.8(6) . . ? C28 N4 Co4 124.0(5) . . ? C24 N4 Co4 120.9(4) . . ? C31 N6 C31 83(2) . 2_667 ? Co1 O1 H1B 110.2 . . ? Co1 O1 H1C 110.4 . . ? H1B O1 H1C 108.7 . . ? Co1 O2 H2C 114.9 . . ? Co1 O2 H2D 131.5 . . ? H2C O2 H2D 108.3 . . ? Co2 O3 H3B 108.6 . . ? Co2 O3 H3C 108.8 . . ? H3B O3 H3C 107.8 . . ? S1 O4 Co2 136.2(3) . . ? Co3 O8 H8A 109.5 . . ? Co3 O8 H8B 109.5 . . ? H8A O8 H8B 109.5 . . ? Co3 O9 H9B 110.4 . . ? Co3 O9 H9C 110.3 . . ? H9B O9 H9C 108.7 . . ? Co4 O10 H10B 111.8 . . ? Co4 O10 H10C 111.8 . . ? H10B O10 H10C 109.6 . . ? S2 O11 Co4 131.2(3) . . ? H15B O15 H15C 108.4 . . ? O5 S1 O6 110.0(3) . . ? O5 S1 O7 111.1(3) . . ? O6 S1 O7 109.1(3) . . ? O5 S1 O4 109.2(3) . . ? O6 S1 O4 109.9(3) . . ? O7 S1 O4 107.5(3) . . ? O14' S2 O13' 129(4) . . ? O14' S2 O13 61(2) . . ? O13' S2 O13 124(3) . . ? O14' S2 O14 129.0(17) . . ? O13' S2 O14 13(4) . . ? O13 S2 O14 111.8(8) . . ? O14' S2 O12 48(2) . . ? O13' S2 O12 99(3) . . ? O13 S2 O12 108.3(6) . . ? O14 S2 O12 108.0(7) . . ? O14' S2 O11 118.9(14) . . ? O13' S2 O11 106(3) . . ? O13 S2 O11 110.8(4) . . ? O14 S2 O11 110.8(7) . . ? O12 S2 O11 107.0(4) . . ? O14' S2 O12' 101(2) . . ? O13' S2 O12' 97(3) . . ? O13 S2 O12' 40.1(15) . . ? O14 S2 O12' 84.1(17) . . ? O12 S2 O12' 147.0(15) . . ? O11 S2 O12' 96.4(11) . . ? C12 C1 C7 125.2(5) . . ? C12 C1 C2 117.1(5) . . ? C7 C1 C2 116.9(5) . . ? C4 C2 C3 120.3(6) 2_675 . ? C4 C2 C1 119.6(6) 2_675 . ? C3 C2 C1 120.0(6) . . ? C2 C3 C4 120.2(6) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C2 C4 C3 119.5(6) 2_675 . ? C2 C4 H4 120.2 2_675 . ? C3 C4 H4 120.2 . . ? N1 C5 C6 123.8(6) . . ? N1 C5 H5 118.1 . . ? C6 C5 H5 118.1 . . ? C5 C6 C7 120.1(6) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C8 116.5(6) . . ? C6 C7 C1 120.6(6) . . ? C8 C7 C1 122.8(6) . . ? C9 C8 C7 119.0(6) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? N1 C9 C8 125.3(6) . . ? N1 C9 H9 117.4 . . ? C8 C9 H9 117.4 . . ? N2 C10 C11 123.6(6) . . ? N2 C10 H10 118.2 . . ? C11 C10 H10 118.2 . . ? C10 C11 C12 119.6(6) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C13 C12 C11 117.0(6) . . ? C13 C12 C1 119.8(6) . . ? C11 C12 C1 123.2(6) . . ? C14 C13 C12 120.2(6) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? N2 C14 C13 123.0(6) . . ? N2 C14 H14 118.5 . . ? C13 C14 H14 118.5 . . ? C21 C15 C26 124.7(5) . . ? C21 C15 C16 118.1(5) . . ? C26 C15 C16 116.7(5) . . ? C17 C16 C18 119.6(6) . 2_656 ? C17 C16 C15 119.7(6) . . ? C18 C16 C15 120.6(6) 2_656 . ? C18 C17 C16 121.1(6) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C16 119.3(6) . 2_656 ? C17 C18 H18 120.3 . . ? C16 C18 H18 120.3 2_656 . ? N3 C19 C20 125.5(6) . . ? N3 C19 H19 117.2 . . ? C20 C19 H19 117.2 . . ? C19 C20 C21 118.4(6) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? C20 C21 C22 117.8(6) . . ? C20 C21 C15 122.3(6) . . ? C22 C21 C15 119.9(6) . . ? C23 C22 C21 119.2(6) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? N3 C23 C22 124.2(6) . . ? N3 C23 H23 117.9 . . ? C22 C23 H23 117.9 . . ? N4 C24 C25 124.5(6) . . ? N4 C24 H24 117.7 . . ? C25 C24 H24 117.7 . . ? C24 C25 C26 119.2(7) . . ? C24 C25 H25 120.4 . . ? C26 C25 H25 120.4 . . ? C27 C26 C25 117.0(6) . . ? C27 C26 C15 120.7(6) . . ? C25 C26 C15 122.2(6) . . ? C26 C27 C28 120.3(6) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? N4 C28 C27 124.2(7) . . ? N4 C28 H28 117.9 . . ? C27 C28 H28 117.9 . . ? N5 C29 C30 160(5) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N6 C31 C32 147(3) . . ? N6 C31 N6 97(2) . 2_667 ? C32 C31 N6 116(3) . 2_667 ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 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 O2 Co1 N1 C9 27.7(5) . . . . ? O2 Co1 N1 C9 -152.3(5) 2_776 . . . ? O1 Co1 N1 C9 -62.0(5) 2_776 . . . ? O1 Co1 N1 C9 118.0(5) . . . . ? N1 Co1 N1 C9 100(100) 2_776 . . . ? O2 Co1 N1 C5 -155.2(5) . . . . ? O2 Co1 N1 C5 24.8(5) 2_776 . . . ? O1 Co1 N1 C5 115.1(5) 2_776 . . . ? O1 Co1 N1 C5 -64.9(5) . . . . ? N1 Co1 N1 C5 -83(100) 2_776 . . . ? O4 Co2 N2 C10 29.8(5) . . . . ? O4 Co2 N2 C10 -150.2(5) 2_565 . . . ? N2 Co2 N2 C10 -132(100) 2_565 . . . ? O3 Co2 N2 C10 -59.0(5) . . . . ? O3 Co2 N2 C10 121.0(5) 2_565 . . . ? O4 Co2 N2 C14 -151.8(5) . . . . ? O4 Co2 N2 C14 28.2(5) 2_565 . . . ? N2 Co2 N2 C14 46(100) 2_565 . . . ? O3 Co2 N2 C14 119.4(5) . . . . ? O3 Co2 N2 C14 -60.6(5) 2_565 . . . ? O8 Co3 N3 C19 141.2(5) 2 . . . ? O8 Co3 N3 C19 -38.8(5) . . . . ? N3 Co3 N3 C19 58(63) 2 . . . ? O9 Co3 N3 C19 -125.0(5) . . . . ? O9 Co3 N3 C19 55.0(5) 2 . . . ? O8 Co3 N3 C23 -44.3(5) 2 . . . ? O8 Co3 N3 C23 135.7(5) . . . . ? N3 Co3 N3 C23 -127(63) 2 . . . ? O9 Co3 N3 C23 49.5(5) . . . . ? O9 Co3 N3 C23 -130.5(5) 2 . . . ? O10 Co4 N4 C28 7.5(5) 2_766 . . . ? O10 Co4 N4 C28 -172.5(5) . . . . ? O11 Co4 N4 C28 -79.5(5) 2_766 . . . ? O11 Co4 N4 C28 100.5(5) . . . . ? N4 Co4 N4 C28 -136(100) 2_766 . . . ? O10 Co4 N4 C24 -166.3(5) 2_766 . . . ? O10 Co4 N4 C24 13.7(5) . . . . ? O11 Co4 N4 C24 106.7(5) 2_766 . . . ? O11 Co4 N4 C24 -73.3(5) . . . . ? N4 Co4 N4 C24 50(100) 2_766 . . . ? O4 Co2 O4 S1 103(100) 2_565 . . . ? N2 Co2 O4 S1 -96.4(4) 2_565 . . . ? N2 Co2 O4 S1 83.6(4) . . . . ? O3 Co2 O4 S1 173.1(4) . . . . ? O3 Co2 O4 S1 -6.9(4) 2_565 . . . ? O10 Co4 O11 S2 -148.2(4) 2_766 . . . ? O10 Co4 O11 S2 31.8(4) . . . . ? O11 Co4 O11 S2 19(100) 2_766 . . . ? N4 Co4 O11 S2 120.9(4) . . . . ? N4 Co4 O11 S2 -59.1(4) 2_766 . . . ? Co2 O4 S1 O5 -103.4(5) . . . . ? Co2 O4 S1 O6 17.4(5) . . . . ? Co2 O4 S1 O7 136.0(4) . . . . ? Co4 O11 S2 O14' 1(3) . . . . ? Co4 O11 S2 O13' -154(4) . . . . ? Co4 O11 S2 O13 68.6(7) . . . . ? Co4 O11 S2 O14 -166.7(7) . . . . ? Co4 O11 S2 O12 -49.2(7) . . . . ? Co4 O11 S2 O12' 107.2(19) . . . . ? C12 C1 C2 C4 -128.0(7) . . . 2_675 ? C7 C1 C2 C4 61.6(8) . . . 2_675 ? C12 C1 C2 C3 54.7(9) . . . . ? C7 C1 C2 C3 -115.7(7) . . . . ? C4 C2 C3 C4 -1.3(11) 2_675 . . . ? C1 C2 C3 C4 176.0(6) . . . . ? C2 C3 C4 C2 1.3(11) . . . 2_675 ? C9 N1 C5 C6 1.0(10) . . . . ? Co1 N1 C5 C6 -176.4(5) . . . . ? N1 C5 C6 C7 -1.1(11) . . . . ? C5 C6 C7 C8 0.3(10) . . . . ? C5 C6 C7 C1 -178.7(6) . . . . ? C12 C1 C7 C6 -153.7(7) . . . . ? C2 C1 C7 C6 15.8(9) . . . . ? C12 C1 C7 C8 27.3(10) . . . . ? C2 C1 C7 C8 -163.2(6) . . . . ? C6 C7 C8 C9 0.5(9) . . . . ? C1 C7 C8 C9 179.5(6) . . . . ? C5 N1 C9 C8 -0.1(10) . . . . ? Co1 N1 C9 C8 177.1(5) . . . . ? C7 C8 C9 N1 -0.6(10) . . . . ? C14 N2 C10 C11 0.0(10) . . . . ? Co2 N2 C10 C11 178.5(5) . . . . ? N2 C10 C11 C12 0.9(10) . . . . ? C10 C11 C12 C13 -0.6(10) . . . . ? C10 C11 C12 C1 176.2(6) . . . . ? C7 C1 C12 C13 -158.4(6) . . . . ? C2 C1 C12 C13 32.1(9) . . . . ? C7 C1 C12 C11 24.8(10) . . . . ? C2 C1 C12 C11 -144.7(6) . . . . ? C11 C12 C13 C14 -0.6(10) . . . . ? C1 C12 C13 C14 -177.5(6) . . . . ? C10 N2 C14 C13 -1.3(10) . . . . ? Co2 N2 C14 C13 -179.8(5) . . . . ? C12 C13 C14 N2 1.6(11) . . . . ? C21 C15 C16 C17 117.7(7) . . . . ? C26 C15 C16 C17 -54.2(9) . . . . ? C21 C15 C16 C18 -59.4(9) . . . 2_656 ? C26 C15 C16 C18 128.7(7) . . . 2_656 ? C18 C16 C17 C18 0.3(11) 2_656 . . . ? C15 C16 C17 C18 -176.8(6) . . . . ? C16 C17 C18 C16 -0.3(11) . . . 2_656 ? C23 N3 C19 C20 1.4(9) . . . . ? Co3 N3 C19 C20 176.1(5) . . . . ? N3 C19 C20 C21 0.7(10) . . . . ? C19 C20 C21 C22 -2.7(9) . . . . ? C19 C20 C21 C15 179.4(6) . . . . ? C26 C15 C21 C20 -26.9(10) . . . . ? C16 C15 C21 C20 162.0(6) . . . . ? C26 C15 C21 C22 155.3(6) . . . . ? C16 C15 C21 C22 -15.8(9) . . . . ? C20 C21 C22 C23 2.5(9) . . . . ? C15 C21 C22 C23 -179.6(6) . . . . ? C19 N3 C23 C22 -1.6(9) . . . . ? Co3 N3 C23 C22 -176.7(5) . . . . ? C21 C22 C23 N3 -0.4(10) . . . . ? C28 N4 C24 C25 0.4(10) . . . . ? Co4 N4 C24 C25 174.8(5) . . . . ? N4 C24 C25 C26 -0.8(11) . . . . ? C24 C25 C26 C27 0.6(10) . . . . ? C24 C25 C26 C15 -175.7(6) . . . . ? C21 C15 C26 C27 156.2(7) . . . . ? C16 C15 C26 C27 -32.5(9) . . . . ? C21 C15 C26 C25 -27.6(10) . . . . ? C16 C15 C26 C25 143.7(7) . . . . ? C25 C26 C27 C28 -0.1(11) . . . . ? C15 C26 C27 C28 176.3(6) . . . . ? C24 N4 C28 C27 0.2(10) . . . . ? Co4 N4 C28 C27 -174.0(5) . . . . ? C26 C27 C28 N4 -0.3(11) . . . . ? C31 N6 C31 C32 178(4) 2_667 . . . ? C31 N6 C31 N6 0.000(1) 2_667 . . 2_667 ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.155 _refine_diff_density_min -0.635 _refine_diff_density_rms 0.125 _database_code_depnum_ccdc_archive 'CCDC 939485' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cu _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H38 Cu N6 O8' _chemical_formula_weight 698.22 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' 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 7.01610(10) _cell_length_b 7.86470(10) _cell_length_c 15.6706(2) _cell_angle_alpha 79.5240(10) _cell_angle_beta 78.1340(10) _cell_angle_gamma 67.6390(10) _cell_volume 777.444(18) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 365 _exptl_absorpt_coefficient_mu 0.765 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8620 _exptl_absorpt_correction_T_max 0.9700 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7525 _diffrn_reflns_av_R_equivalents 0.0137 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3559 _reflns_number_gt 3252 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0425P)^2^+0.5855P] 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 3559 _refine_ls_number_parameters 228 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 C1 C -0.3362(2) 0.4282(2) 0.31782(10) 0.0156(3) Uani 1 1 d . . . H1 H -0.4704 0.4239 0.3194 0.019 Uiso 1 1 calc R . . C2 C -0.1953(2) 0.3948(2) 0.24139(9) 0.0138(3) Uani 1 1 d . . . H2 H -0.2330 0.3695 0.1915 0.017 Uiso 1 1 calc R . . C3 C 0.0033(2) 0.39880(19) 0.23858(9) 0.0120(3) Uani 1 1 d . . . C4 C 0.0474(2) 0.4425(2) 0.31280(10) 0.0156(3) Uani 1 1 d . . . H4 H 0.1794 0.4501 0.3128 0.019 Uiso 1 1 calc R . . C5 C -0.1032(2) 0.4746(2) 0.38647(10) 0.0169(3) Uani 1 1 d . . . H5 H -0.0713 0.5037 0.4368 0.020 Uiso 1 1 calc R . . C6 C 0.3592(2) 0.24428(19) 0.16524(9) 0.0127(3) Uani 1 1 d . . . C7 C 0.4213(2) 0.1240(2) 0.24033(10) 0.0154(3) Uani 1 1 d . . . H7 H 0.3227 0.1210 0.2917 0.018 Uiso 1 1 calc R . . C8 C 0.6278(2) 0.0098(2) 0.23878(11) 0.0179(3) Uani 1 1 d . . . H8 H 0.6667 -0.0700 0.2905 0.022 Uiso 1 1 calc R . . C9 C 0.7154(2) 0.1190(2) 0.09751(10) 0.0177(3) Uani 1 1 d . . . H9 H 0.8173 0.1164 0.0469 0.021 Uiso 1 1 calc R . . C10 C 0.5136(2) 0.2411(2) 0.09226(10) 0.0154(3) Uani 1 1 d . . . H10 H 0.4805 0.3215 0.0400 0.018 Uiso 1 1 calc R . . C11 C 0.0771(2) 0.4295(2) 0.07904(9) 0.0119(3) Uani 1 1 d . . . C12 C 0.1149(2) 0.3114(2) 0.01637(9) 0.0129(3) Uani 1 1 d . . . H12A H 0.1929 0.1831 0.0275 0.016 Uiso 1 1 calc R . . C13 C -0.0378(2) 0.6178(2) 0.06267(9) 0.0132(3) Uani 1 1 d . . . H13 H -0.0634 0.6979 0.1057 0.016 Uiso 1 1 calc R . . C14 C -0.2171(2) 0.1731(2) 0.58197(10) 0.0172(3) Uani 1 1 d . . . C15 C -0.0233(3) 0.0772(2) 0.62472(11) 0.0229(3) Uani 1 1 d . . . H15A H 0.0480 -0.0477 0.6070 0.034 Uiso 1 1 calc R . . H15B H -0.0619 0.0691 0.6887 0.034 Uiso 1 1 calc R . . H15C H 0.0700 0.1478 0.6063 0.034 Uiso 1 1 calc R . . C16 C 0.3576(3) 0.7455(2) 0.16083(12) 0.0242(3) Uani 1 1 d . . . H16A H 0.4989 0.7396 0.1344 0.036 Uiso 1 1 calc R . . H16B H 0.3355 0.6361 0.1499 0.036 Uiso 1 1 calc R . . H16C H 0.3401 0.7490 0.2242 0.036 Uiso 1 1 calc R . . Cu1 Cu -0.5000 0.5000 0.5000 0.02199(10) Uani 1 2 d S . . H3 H 0.0946(18) 0.910(3) 0.1517(11) 0.013(4) Uiso 1 1 d D . . H11 H -0.530(3) 0.172(3) 0.4965(16) 0.052(8) Uiso 1 1 d D . . H12 H -0.667(4) 0.163(3) 0.4540(15) 0.034(6) Uiso 1 1 d D . . N1 N -0.2922(2) 0.46644(17) 0.39001(8) 0.0151(2) Uani 1 1 d . . . N2 N 0.15156(19) 0.36072(17) 0.16184(8) 0.0126(2) Uani 1 1 d . . . N3 N 0.7770(2) 0.00392(18) 0.16930(9) 0.0188(3) Uani 1 1 d . . . O1 O -0.27442(18) 0.34841(16) 0.56747(7) 0.0213(2) Uani 1 1 d . . . O2 O -0.3079(2) 0.0793(2) 0.56401(9) 0.0369(3) Uani 1 1 d . . . O3 O 0.21207(19) 0.90555(18) 0.12362(9) 0.0290(3) Uani 1 1 d D . . O1W O -0.6252(3) 0.23910(19) 0.46753(10) 0.0371(3) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0115(7) 0.0181(7) 0.0156(7) -0.0010(5) -0.0014(5) -0.0041(5) C2 0.0135(7) 0.0161(7) 0.0118(6) -0.0023(5) -0.0025(5) -0.0047(5) C3 0.0117(6) 0.0115(6) 0.0099(6) -0.0001(5) -0.0009(5) -0.0018(5) C4 0.0122(7) 0.0205(7) 0.0144(7) -0.0031(5) -0.0024(5) -0.0056(6) C5 0.0168(7) 0.0212(7) 0.0119(7) -0.0038(5) -0.0025(5) -0.0048(6) C6 0.0106(6) 0.0135(6) 0.0140(7) -0.0033(5) -0.0026(5) -0.0033(5) C7 0.0143(7) 0.0169(7) 0.0139(7) -0.0012(5) -0.0022(5) -0.0046(6) C8 0.0172(7) 0.0160(7) 0.0198(7) -0.0017(6) -0.0078(6) -0.0027(6) C9 0.0131(7) 0.0215(7) 0.0190(7) -0.0084(6) 0.0002(6) -0.0053(6) C10 0.0135(7) 0.0188(7) 0.0137(7) -0.0033(5) -0.0015(5) -0.0052(6) C11 0.0089(6) 0.0171(7) 0.0088(6) 0.0001(5) -0.0008(5) -0.0046(5) C12 0.0115(6) 0.0123(6) 0.0129(7) -0.0015(5) -0.0009(5) -0.0023(5) C13 0.0126(6) 0.0147(7) 0.0116(6) -0.0034(5) -0.0002(5) -0.0041(5) C14 0.0154(7) 0.0238(8) 0.0108(7) -0.0011(5) -0.0002(5) -0.0065(6) C15 0.0189(8) 0.0217(8) 0.0237(8) 0.0037(6) -0.0068(6) -0.0034(6) C16 0.0199(8) 0.0221(8) 0.0261(9) -0.0010(6) -0.0032(6) -0.0035(6) Cu1 0.01413(14) 0.02556(16) 0.01057(14) 0.00385(10) 0.00298(10) 0.00513(11) N1 0.0142(6) 0.0168(6) 0.0104(6) -0.0013(4) -0.0001(5) -0.0023(5) N2 0.0100(6) 0.0169(6) 0.0082(5) -0.0013(4) -0.0013(4) -0.0019(5) N3 0.0125(6) 0.0183(6) 0.0244(7) -0.0081(5) -0.0045(5) -0.0009(5) O1 0.0176(5) 0.0216(6) 0.0153(5) 0.0017(4) -0.0011(4) 0.0008(4) O2 0.0423(8) 0.0517(9) 0.0310(7) -0.0039(6) -0.0120(6) -0.0296(7) O3 0.0171(6) 0.0307(7) 0.0326(7) 0.0096(5) -0.0050(5) -0.0066(5) O1W 0.0449(9) 0.0219(7) 0.0398(8) -0.0012(6) -0.0028(7) -0.0098(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 C1 N1 1.343(2) . ? C1 C2 1.382(2) . ? C2 C3 1.397(2) . ? C3 C4 1.393(2) . ? C3 N2 1.4132(18) . ? C4 C5 1.384(2) . ? C5 N1 1.341(2) . ? C6 C7 1.400(2) . ? C6 C10 1.401(2) . ? C6 N2 1.4011(18) . ? C7 C8 1.382(2) . ? C8 N3 1.340(2) . ? C9 N3 1.343(2) . ? C9 C10 1.385(2) . ? C11 C12 1.391(2) . ? C11 C13 1.395(2) . ? C11 N2 1.4343(17) . ? C12 C13 1.390(2) 2_565 ? C13 C12 1.390(2) 2_565 ? C14 O2 1.239(2) . ? C14 O1 1.271(2) . ? C14 C15 1.509(2) . ? C16 O3 1.402(2) . ? Cu1 O1 1.9592(11) . ? Cu1 O1 1.9592(11) 2_466 ? Cu1 N1 2.0014(12) 2_466 ? Cu1 N1 2.0014(12) . ? Cu1 O1W 2.6789(15) . ? 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 N1 C1 C2 123.05(14) . . ? C1 C2 C3 119.04(13) . . ? C4 C3 C2 117.90(13) . . ? C4 C3 N2 122.07(13) . . ? C2 C3 N2 120.03(13) . . ? C5 C4 C3 119.18(14) . . ? N1 C5 C4 122.98(14) . . ? C7 C6 C10 117.09(13) . . ? C7 C6 N2 121.98(13) . . ? C10 C6 N2 120.92(13) . . ? C8 C7 C6 119.13(14) . . ? N3 C8 C7 124.53(14) . . ? N3 C9 C10 124.47(15) . . ? C9 C10 C6 118.95(14) . . ? C12 C11 C13 120.16(13) . . ? C12 C11 N2 121.07(13) . . ? C13 C11 N2 118.76(13) . . ? C13 C12 C11 119.57(13) 2_565 . ? C12 C13 C11 120.27(13) 2_565 . ? O2 C14 O1 125.05(15) . . ? O2 C14 C15 119.29(15) . . ? O1 C14 C15 115.66(14) . . ? O1 Cu1 O1 180.000(1) . 2_466 ? O1 Cu1 N1 90.85(5) . 2_466 ? O1 Cu1 N1 89.15(5) 2_466 2_466 ? O1 Cu1 N1 89.15(5) . . ? O1 Cu1 N1 90.85(5) 2_466 . ? N1 Cu1 N1 180.000(1) 2_466 . ? O1 Cu1 O1W 100.54(5) . . ? O1 Cu1 O1W 79.46(5) 2_466 . ? N1 Cu1 O1W 89.08(5) 2_466 . ? N1 Cu1 O1W 90.92(5) . . ? C5 N1 C1 117.81(13) . . ? C5 N1 Cu1 121.70(10) . . ? C1 N1 Cu1 120.45(10) . . ? C6 N2 C3 121.88(12) . . ? C6 N2 C11 120.39(12) . . ? C3 N2 C11 117.40(11) . . ? C8 N3 C9 115.82(13) . . ? C14 O1 Cu1 122.96(11) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.415 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 939486'