# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Paul Donnelly' _publ_contact_author_email PAULD@UNIMELB.EDU.AU _publ_section_title ; New bifunctional chelators for copper radiopharmaceuticals: Cage amine ligands conjugated to the tumour targeting peptides [Tyr]3-octreotate and [Lys]3-bombesin ; loop_ _publ_author_name 'Paul Donnelly' 'John A. Karas' 'Michelle T. Ma' 'Denis Scanlon' 'Jonathan M White' # Attachment 'jmwpd53.cif' data_jmwpd53 _database_code_depnum_ccdc_archive 'CCDC 720001' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H41 Cu N11 O12' _chemical_formula_weight 679.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.345(5) _cell_length_b 12.231(5) _cell_length_c 26.941(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.658(5) _cell_angle_gamma 90.00 _cell_volume 2744(2) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1118 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 26.89 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_min 0.01 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1428 _exptl_absorpt_coefficient_mu 0.879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 17656 _diffrn_reflns_av_R_equivalents 0.1869 _diffrn_reflns_av_sigmaI/netI 0.2390 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4834 _reflns_number_gt 2010 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0596P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0114(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4834 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1648 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.1524 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 0.785 _refine_ls_restrained_S_all 0.785 _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 Cu Cu 0.56552(10) 0.24255(7) 0.36183(3) 0.0237(3) Uani 1 1 d . . . O5 O -0.0263(6) 0.5263(4) 0.30407(18) 0.0336(13) Uani 1 1 d . . . O9 O 0.1441(6) 0.2995(4) 0.24029(19) 0.0371(14) Uani 1 1 d . . . O11 O 0.4747(6) 0.4046(4) 0.09363(17) 0.0337(13) Uani 1 1 d . . . O10 O 0.6530(6) 0.3773(4) 0.15418(18) 0.0305(13) Uani 1 1 d . . . O12 O 0.5221(6) 0.2387(4) 0.12042(17) 0.0398(14) Uani 1 1 d . . . O6 O 0.2281(6) 0.5058(4) 0.32319(18) 0.0348(14) Uani 1 1 d . . . O4 O 0.0570(6) 0.3880(4) 0.35052(17) 0.0326(14) Uani 1 1 d . . . O2 O 0.0847(7) 0.4484(4) 0.5556(2) 0.0415(15) Uani 1 1 d . . . N7 N 0.3192(9) 0.2258(6) 0.5102(3) 0.0308(19) Uani 1 1 d . . . O1 O 0.0589(6) 0.2461(4) 0.48009(17) 0.0321(12) Uani 1 1 d . . . O7 O 0.3175(6) 0.4091(4) 0.20927(19) 0.0370(14) Uani 1 1 d . . . N5 N 0.4515(7) 0.2015(4) 0.2845(2) 0.0249(15) Uani 1 1 d . . . H5 H 0.3943 0.2605 0.2729 0.030 Uiso 1 1 calc R . . N10 N 0.1752(8) 0.3746(5) 0.2095(2) 0.0325(16) Uani 1 1 d . . . N1 N 0.6935(7) 0.2218(4) 0.4439(2) 0.0258(15) Uani 1 1 d . . . H1 H 0.7709 0.2735 0.4497 0.031 Uiso 1 1 calc R . . C16 C 0.1089(9) 0.1904(6) 0.5652(3) 0.032(2) Uani 1 1 d . . . H16A H 0.1752 0.2300 0.5900 0.038 Uiso 1 1 calc R . . H16B H 0.1318 0.1132 0.5698 0.038 Uiso 1 1 calc R . . N4 N 0.7487(6) 0.1351(4) 0.3449(2) 0.0243(15) Uani 1 1 d . . . H4 H 0.7027 0.0692 0.3375 0.029 Uiso 1 1 calc R . . N9 N 0.0849(8) 0.4729(5) 0.3257(2) 0.0272(15) Uani 1 1 d . . . O8 O 0.0657(6) 0.4106(4) 0.18149(19) 0.0376(14) Uani 1 1 d . . . N6 N 0.6916(7) 0.3636(4) 0.3316(2) 0.0268(15) Uani 1 1 d . . . H6 H 0.7922 0.3636 0.3467 0.032 Uiso 1 1 calc R . . N11 N 0.5486(8) 0.3392(5) 0.1228(2) 0.0288(16) Uani 1 1 d . . . C12 C 0.8369(8) 0.1696(5) 0.3016(2) 0.0212(17) Uani 1 1 d . . . H12A H 0.8819 0.1054 0.2866 0.025 Uiso 1 1 calc R . . H12B H 0.9253 0.2165 0.3130 0.025 Uiso 1 1 calc R . . N2 N 0.4042(7) 0.1287(5) 0.3818(2) 0.0265(16) Uani 1 1 d . . . H2 H 0.4531 0.0624 0.3801 0.032 Uiso 1 1 calc R . . N8 N 0.8239(7) 0.2306(4) 0.21636(18) 0.0255(15) Uani 1 1 d . . . H8A H 0.7678 0.2659 0.1921 0.038 Uiso 1 1 calc R . . H8B H 0.8408 0.1621 0.2069 0.038 Uiso 1 1 calc R . . H8C H 0.9177 0.2640 0.2227 0.038 Uiso 1 1 calc R . . C15 C 0.1588(10) 0.2232(5) 0.5147(3) 0.0277(19) Uani 1 1 d . . . C1 C 0.4015(9) 0.2315(6) 0.4642(3) 0.0280(18) Uani 1 1 d . . . C13 C 0.7067(8) 0.3506(5) 0.2767(2) 0.0229(18) Uani 1 1 d . . . H13A H 0.7966 0.3939 0.2668 0.028 Uiso 1 1 calc R . . H13B H 0.6102 0.3781 0.2590 0.028 Uiso 1 1 calc R . . C7 C 0.5482(8) 0.4594(5) 0.3941(3) 0.0268(19) Uani 1 1 d . . . H7A H 0.6352 0.4485 0.4192 0.032 Uiso 1 1 calc R . . H7B H 0.4906 0.5254 0.4020 0.032 Uiso 1 1 calc R . . C9 C 0.3384(8) 0.1117(5) 0.2932(2) 0.0251(18) Uani 1 1 d . . . H9A H 0.3940 0.0420 0.2929 0.030 Uiso 1 1 calc R . . H9B H 0.2528 0.1108 0.2672 0.030 Uiso 1 1 calc R . . C6 C 0.2696(9) 0.1293(5) 0.3431(2) 0.0266(19) Uani 1 1 d . . . H6A H 0.2134 0.1986 0.3434 0.032 Uiso 1 1 calc R . . H6B H 0.1941 0.0715 0.3496 0.032 Uiso 1 1 calc R . . C2 C 0.3421(9) 0.1370(6) 0.4319(3) 0.031(2) Uani 1 1 d . . . H2A H 0.3686 0.0697 0.4497 0.038 Uiso 1 1 calc R . . H2B H 0.2259 0.1415 0.4280 0.038 Uiso 1 1 calc R . . C5 C 0.7656(8) 0.1142(5) 0.4366(2) 0.0247(18) Uani 1 1 d . . . H5A H 0.6824 0.0589 0.4326 0.030 Uiso 1 1 calc R . . H5B H 0.8362 0.0951 0.4653 0.030 Uiso 1 1 calc R . . N3 N 0.4377(7) 0.3635(5) 0.3923(2) 0.0312(16) Uani 1 1 d . . . H3 H 0.3559 0.3801 0.3696 0.037 Uiso 1 1 calc R . . C14 C 0.7321(9) 0.2304(5) 0.2621(3) 0.0269(18) Uani 1 1 d . . . C10 C 0.6132(9) 0.4693(5) 0.3435(3) 0.0272(19) Uani 1 1 d . . . H10A H 0.5267 0.4851 0.3188 0.033 Uiso 1 1 calc R . . H10B H 0.6907 0.5283 0.3434 0.033 Uiso 1 1 calc R . . C18 C -0.0985(9) 0.3287(6) 0.5917(3) 0.037(2) Uani 1 1 d . . . H18A H -0.2102 0.3356 0.5992 0.044 Uiso 1 1 calc R . . H18B H -0.0327 0.3452 0.6218 0.044 Uiso 1 1 calc R . . C11 C 0.5729(8) 0.1743(5) 0.2486(2) 0.0216(17) Uani 1 1 d . . . H11A H 0.5337 0.1968 0.2155 0.026 Uiso 1 1 calc R . . H11B H 0.5890 0.0957 0.2481 0.026 Uiso 1 1 calc R . . C17 C -0.0653(9) 0.2096(5) 0.5752(3) 0.034(2) Uani 1 1 d . . . H17A H -0.0953 0.1597 0.6010 0.040 Uiso 1 1 calc R . . H17B H -0.1319 0.1934 0.5453 0.040 Uiso 1 1 calc R . . C3 C 0.5786(8) 0.2238(6) 0.4826(2) 0.0275(19) Uani 1 1 d . . . H3A H 0.6038 0.2857 0.5042 0.033 Uiso 1 1 calc R . . H3B H 0.5933 0.1581 0.5025 0.033 Uiso 1 1 calc R . . C8 C 0.8612(9) 0.1196(6) 0.3899(2) 0.0290(19) Uani 1 1 d . . . H8D H 0.9366 0.1800 0.3927 0.035 Uiso 1 1 calc R . . H8E H 0.9217 0.0526 0.3867 0.035 Uiso 1 1 calc R . . C4 C 0.3625(9) 0.3420(6) 0.4403(3) 0.031(2) Uani 1 1 d . . . H4A H 0.2469 0.3477 0.4344 0.037 Uiso 1 1 calc R . . H4B H 0.3964 0.3989 0.4637 0.037 Uiso 1 1 calc R . . O3 O -0.1629(7) 0.4332(4) 0.5180(2) 0.0436(15) Uani 1 1 d . . . C19 C -0.0622(12) 0.4094(6) 0.5518(3) 0.038(2) Uani 1 1 d . . . H H 0.123(10) 0.512(7) 0.525(3) 0.08(3) Uiso 1 1 d . . . H7 H 0.357(9) 0.207(6) 0.532(3) 0.03(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0262(5) 0.0165(5) 0.0287(5) 0.0002(5) 0.0027(4) 0.0004(5) O5 0.027(3) 0.029(3) 0.043(3) 0.009(3) -0.012(3) 0.002(3) O9 0.037(3) 0.030(3) 0.044(4) 0.017(3) 0.001(3) -0.003(3) O11 0.035(3) 0.035(3) 0.030(3) 0.006(3) -0.004(3) 0.006(3) O10 0.028(3) 0.034(3) 0.028(3) -0.002(2) -0.011(3) 0.003(3) O12 0.061(4) 0.014(3) 0.044(3) -0.002(3) -0.001(3) -0.002(3) O6 0.022(3) 0.035(3) 0.047(4) 0.005(3) 0.000(3) -0.002(3) O4 0.035(3) 0.025(3) 0.037(3) 0.011(3) -0.002(3) -0.003(3) O2 0.033(4) 0.040(4) 0.050(4) -0.006(3) -0.005(3) -0.012(3) N7 0.028(4) 0.044(5) 0.021(4) 0.003(4) 0.005(4) 0.005(4) O1 0.031(3) 0.038(3) 0.027(3) 0.002(3) 0.000(2) 0.006(3) O7 0.032(3) 0.032(3) 0.047(4) 0.000(3) 0.002(3) -0.007(3) N5 0.029(4) 0.014(3) 0.033(4) 0.000(3) 0.010(3) -0.005(3) N10 0.035(5) 0.024(4) 0.038(4) -0.005(3) 0.001(4) 0.004(3) N1 0.031(4) 0.016(4) 0.031(4) -0.002(3) 0.010(3) 0.002(3) C16 0.031(5) 0.030(4) 0.035(5) 0.006(4) 0.004(4) -0.001(4) N4 0.019(4) 0.029(4) 0.025(4) -0.004(3) -0.001(3) -0.011(3) N9 0.031(4) 0.022(4) 0.028(4) -0.005(3) -0.005(3) -0.001(3) O8 0.040(4) 0.027(3) 0.043(4) 0.011(3) -0.011(3) -0.001(3) N6 0.022(4) 0.024(4) 0.033(4) -0.006(3) -0.004(3) 0.010(3) N11 0.035(4) 0.017(4) 0.034(4) 0.001(3) 0.002(4) 0.003(3) C12 0.026(4) 0.020(4) 0.017(4) 0.005(3) -0.002(3) 0.002(3) N2 0.027(4) 0.029(4) 0.022(4) 0.002(3) -0.009(3) 0.007(3) N8 0.034(4) 0.015(3) 0.027(4) 0.000(3) -0.002(3) 0.000(3) C15 0.039(5) 0.011(4) 0.035(5) -0.004(3) 0.010(4) 0.000(3) C1 0.033(5) 0.021(4) 0.030(4) 0.001(4) 0.007(4) 0.002(4) C13 0.024(4) 0.019(4) 0.026(5) -0.001(3) 0.003(4) -0.003(3) C7 0.028(5) 0.022(4) 0.030(5) -0.005(4) 0.005(4) 0.001(4) C9 0.015(4) 0.029(4) 0.031(5) 0.006(4) 0.003(4) -0.002(3) C6 0.035(5) 0.024(4) 0.022(4) 0.004(3) 0.006(4) 0.004(4) C2 0.029(5) 0.039(5) 0.027(5) -0.013(4) 0.004(4) -0.001(4) C5 0.027(5) 0.024(4) 0.024(4) 0.000(3) 0.006(4) 0.001(3) N3 0.031(4) 0.036(4) 0.026(4) 0.004(3) 0.003(3) -0.008(3) C14 0.039(5) 0.018(4) 0.025(4) 0.005(3) 0.008(4) 0.003(4) C10 0.032(5) 0.018(4) 0.032(5) 0.004(3) 0.003(4) 0.003(3) C18 0.038(5) 0.041(5) 0.034(5) -0.011(4) 0.014(4) 0.006(4) C11 0.019(4) 0.022(4) 0.023(4) 0.004(3) -0.002(4) 0.000(3) C17 0.035(5) 0.033(5) 0.034(5) 0.004(4) 0.012(4) 0.000(4) C3 0.029(4) 0.031(5) 0.023(4) -0.008(3) 0.005(4) 0.000(3) C8 0.037(5) 0.020(4) 0.030(5) -0.003(4) -0.001(4) 0.003(4) C4 0.039(5) 0.031(5) 0.025(5) 0.004(4) 0.007(4) 0.008(4) O3 0.038(4) 0.031(3) 0.062(4) 0.001(3) -0.007(3) 0.004(3) C19 0.047(6) 0.024(5) 0.044(6) -0.012(4) 0.003(5) 0.013(4) _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 Cu N6 2.018(6) . ? Cu N3 2.028(6) . ? Cu N2 2.033(6) . ? Cu N4 2.088(6) . ? Cu N5 2.289(6) . ? Cu N1 2.406(6) . ? O5 N9 1.248(7) . ? O9 N10 1.276(7) . ? O11 N11 1.255(7) . ? O10 N11 1.264(7) . ? O12 N11 1.249(7) . ? O6 N9 1.267(7) . ? O4 N9 1.264(7) . ? O2 C19 1.314(9) . ? N7 C15 1.352(10) . ? N7 C1 1.458(9) . ? O1 C15 1.243(8) . ? O7 N10 1.261(7) . ? N5 C9 1.477(8) . ? N5 C11 1.484(8) . ? N10 O8 1.228(7) . ? N1 C3 1.462(8) . ? N1 C5 1.465(8) . ? C16 C15 1.501(9) . ? C16 C17 1.513(9) . ? N4 C12 1.481(8) . ? N4 C8 1.497(8) . ? N6 C10 1.492(8) . ? N6 C13 1.499(8) . ? C12 C14 1.527(9) . ? N2 C2 1.481(8) . ? N2 C6 1.482(8) . ? N8 C14 1.492(8) . ? C1 C2 1.510(9) . ? C1 C4 1.524(9) . ? C1 C3 1.532(9) . ? C13 C14 1.540(9) . ? C7 N3 1.491(8) . ? C7 C10 1.502(8) . ? C9 C6 1.511(9) . ? C5 C8 1.535(9) . ? N3 C4 1.494(8) . ? C14 C11 1.518(9) . ? C18 C19 1.505(10) . ? C18 C17 1.554(9) . ? O3 C19 1.234(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 Cu N3 86.0(2) . . ? N6 Cu N2 168.6(2) . . ? N3 Cu N2 91.0(2) . . ? N6 Cu N4 88.1(2) . . ? N3 Cu N4 163.5(2) . . ? N2 Cu N4 97.6(2) . . ? N6 Cu N5 89.5(2) . . ? N3 Cu N5 109.3(2) . . ? N2 Cu N5 81.2(2) . . ? N4 Cu N5 86.1(2) . . ? N6 Cu N1 103.7(2) . . ? N3 Cu N1 85.3(2) . . ? N2 Cu N1 87.0(2) . . ? N4 Cu N1 81.1(2) . . ? N5 Cu N1 161.23(18) . . ? C15 N7 C1 126.9(7) . . ? C9 N5 C11 114.0(5) . . ? C9 N5 Cu 104.6(4) . . ? C11 N5 Cu 112.4(4) . . ? O8 N10 O7 122.8(7) . . ? O8 N10 O9 118.9(7) . . ? O7 N10 O9 118.3(7) . . ? C3 N1 C5 113.8(5) . . ? C3 N1 Cu 112.4(4) . . ? C5 N1 Cu 97.8(4) . . ? C15 C16 C17 116.5(7) . . ? C12 N4 C8 110.9(5) . . ? C12 N4 Cu 113.6(4) . . ? C8 N4 Cu 109.5(4) . . ? O5 N9 O4 121.3(6) . . ? O5 N9 O6 118.9(6) . . ? O4 N9 O6 119.7(6) . . ? C10 N6 C13 111.7(5) . . ? C10 N6 Cu 107.5(4) . . ? C13 N6 Cu 113.5(4) . . ? O12 N11 O11 121.1(6) . . ? O12 N11 O10 120.6(6) . . ? O11 N11 O10 118.3(6) . . ? N4 C12 C14 113.4(5) . . ? C2 N2 C6 110.3(5) . . ? C2 N2 Cu 118.1(4) . . ? C6 N2 Cu 107.2(4) . . ? O1 C15 N7 123.2(7) . . ? O1 C15 C16 121.9(7) . . ? N7 C15 C16 114.9(7) . . ? N7 C1 C2 107.3(6) . . ? N7 C1 C4 107.6(6) . . ? C2 C1 C4 112.5(6) . . ? N7 C1 C3 102.6(6) . . ? C2 C1 C3 114.5(6) . . ? C4 C1 C3 111.5(6) . . ? N6 C13 C14 112.1(5) . . ? N3 C7 C10 107.0(6) . . ? N5 C9 C6 108.6(6) . . ? N2 C6 C9 108.1(6) . . ? N2 C2 C1 117.1(6) . . ? N1 C5 C8 108.0(5) . . ? C7 N3 C4 113.9(6) . . ? C7 N3 Cu 104.3(4) . . ? C4 N3 Cu 118.9(4) . . ? N8 C14 C11 106.8(5) . . ? N8 C14 C12 106.0(5) . . ? C11 C14 C12 113.6(5) . . ? N8 C14 C13 107.2(5) . . ? C11 C14 C13 111.1(6) . . ? C12 C14 C13 111.6(6) . . ? N6 C10 C7 108.3(6) . . ? C19 C18 C17 111.2(6) . . ? N5 C11 C14 111.4(5) . . ? C16 C17 C18 112.8(6) . . ? N1 C3 C1 115.6(6) . . ? N4 C8 C5 109.7(6) . . ? N3 C4 C1 115.5(6) . . ? O3 C19 O2 124.0(8) . . ? O3 C19 C18 121.6(9) . . ? O2 C19 C18 114.3(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.835 _refine_diff_density_min -0.639 _refine_diff_density_rms 0.116 # Attachment 'jmwpd58.cif' data_jmwpd58 _database_code_depnum_ccdc_archive 'CCDC 724226' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_absolute_configuration 'racemic twinning' _chemical_formula_sum 'C25 H46 Cl Cu F3 N8 O9 S' _chemical_formula_weight 790.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'C222(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.4608(13) _cell_length_b 20.445(2) _cell_length_c 13.2263(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3369.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2579 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 26.81 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1652 _exptl_absorpt_coefficient_mu 0.868 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 8848 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2973 _reflns_number_gt 2603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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. The triflate anion was disordered over a two-fold axis, with the sulphur atom lying on the axis and the carbon slightly off-axis. ; _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^)+(0.0674P)^2^+2.7135P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.37(2) _refine_ls_number_reflns 2973 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 C5 C 0.1500(4) 0.8892(2) 0.8854(4) 0.0457(12) Uani 1 1 d . . . H5A H 0.2170 0.8703 0.8621 0.055 Uiso 1 1 calc R . . H5B H 0.0921 0.8711 0.8452 0.055 Uiso 1 1 calc R . . C6 C 0.1330(4) 0.87252(18) 0.9953(4) 0.0413(9) Uani 1 1 d . . . H6A H 0.0614 0.8857 1.0158 0.050 Uiso 1 1 calc R . . H6B H 0.1391 0.8256 1.0047 0.050 Uiso 1 1 calc R . . C13 C 0.4678(10) 0.2306(6) 0.2583(16) 0.076(6) Uani 0.50 1 d P . . O4 O 0.5162(13) 0.1354(5) 0.3632(7) 0.115(4) Uani 0.50 1 d P . . O5 O 0.4257(11) 0.1110(5) 0.3003(10) 0.097(3) Uani 0.50 1 d P . . O6 O 0.3936(8) 0.1369(6) 0.2278(16) 0.126(5) Uani 0.50 1 d P . . F1 F 0.5000 0.2679(7) 0.2500 0.40(2) Uani 1 2 d S . . F2 F 0.4729(11) 0.2472(6) 0.3477(10) 0.115(4) Uani 0.50 1 d P . . F3 F 0.3731(9) 0.2428(4) 0.2312(8) 0.107(3) Uani 0.50 1 d P . . Cl Cl -0.07463(11) 1.0000 1.0000 0.0503(4) Uani 1 2 d S . . H H -0.059(5) 0.712(3) 1.631(4) 0.069(18) Uiso 1 1 d . . . C1 C 0.2447(3) 0.95341(19) 1.2303(3) 0.0308(8) Uani 1 1 d . . . C2 C 0.3630(3) 1.0377(2) 0.8011(3) 0.0357(10) Uani 1 1 d . . . H2A H 0.4014 1.0164 0.7463 0.043 Uiso 1 1 calc R . . H2B H 0.3950 1.0804 0.8112 0.043 Uiso 1 1 calc R . . C3 C 0.1845(4) 0.9809(2) 0.7709(3) 0.0423(11) Uani 1 1 d . . . H3A H 0.1205 0.9847 0.7295 0.051 Uiso 1 1 calc R . . H3B H 0.2299 0.9476 0.7408 0.051 Uiso 1 1 calc R . . C4 C 0.4738(3) 1.0160(2) 0.9487(3) 0.0370(10) Uani 1 1 d . . . H4A H 0.4777 1.0631 0.9564 0.044 Uiso 1 1 calc R . . H4B H 0.5361 1.0018 0.9107 0.044 Uiso 1 1 calc R . . C7 C 0.1866(4) 0.9019(2) 1.1657(3) 0.0373(10) Uani 1 1 d . . . H7A H 0.2056 0.8587 1.1903 0.045 Uiso 1 1 calc R . . H7B H 0.1098 0.9072 1.1744 0.045 Uiso 1 1 calc R . . C8 C 0.2939(3) 0.8803(2) 1.3751(3) 0.0350(10) Uani 1 1 d . . . C9 C 0.2741(4) 0.8653(2) 1.4855(4) 0.0457(12) Uani 1 1 d . . . H9A H 0.2469 0.9039 1.5193 0.055 Uiso 1 1 calc R . . H9B H 0.3410 0.8528 1.5177 0.055 Uiso 1 1 calc R . . C10 C 0.1912(5) 0.8085(3) 1.4948(5) 0.0719(15) Uani 1 1 d . . . H10A H 0.1295 0.8194 1.4534 0.086 Uiso 1 1 calc R . . H10B H 0.2233 0.7694 1.4664 0.086 Uiso 1 1 calc R . . C11 C 0.1537(5) 0.7933(3) 1.5950(5) 0.0671(15) Uani 1 1 d . . . H11A H 0.1178 0.8313 1.6230 0.081 Uiso 1 1 calc R . . H11B H 0.2148 0.7834 1.6378 0.081 Uiso 1 1 calc R . . C12 C 0.0786(4) 0.7370(3) 1.5964(4) 0.0506(12) Uani 1 1 d . . . N1 N 0.3769(2) 0.9987(2) 0.8942(2) 0.0412(8) Uani 1 1 d . . . H1 H 0.3849 0.9564 0.8742 0.049 Uiso 1 1 calc R . . N2 N 0.1532(3) 0.95968(19) 0.8733(3) 0.0471(10) Uani 1 1 d . . . H2 H 0.0845 0.9737 0.8822 0.056 Uiso 1 1 calc R . . N3 N 0.2120(3) 0.9057(2) 1.0575(3) 0.0437(9) Uani 1 1 d . . . H3 H 0.2739 0.8826 1.0496 0.052 Uiso 1 1 calc R . . N4 N 0.2412(3) 0.93192(16) 1.3364(2) 0.0332(7) Uani 1 1 d . . . H4 H 0.2021 0.9543 1.3772 0.040 Uiso 1 1 calc R . . O1 O 0.3532(3) 0.84596(17) 1.3236(3) 0.0528(9) Uani 1 1 d . . . O2 O 0.1049(3) 0.68358(19) 1.5713(4) 0.0695(11) Uani 1 1 d . . . O3 O -0.0173(3) 0.75110(17) 1.6309(4) 0.0650(14) Uani 1 1 d . . . S1 S 0.5000 0.14344(9) 0.2500 0.0629(6) Uani 1 2 d S . . Cu1 Cu 0.24491(6) 1.0000 1.0000 0.0382(2) Uani 1 2 d S . . 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 C5 0.066(3) 0.033(2) 0.038(3) 0.002(2) -0.007(2) -0.021(2) C6 0.060(2) 0.027(2) 0.037(2) 0.003(2) -0.007(3) -0.0155(17) C13 0.080(12) 0.051(7) 0.097(11) 0.045(10) -0.042(12) -0.035(6) O4 0.196(13) 0.092(7) 0.059(6) 0.035(5) 0.015(8) -0.006(9) O5 0.119(10) 0.068(7) 0.104(9) 0.006(6) 0.037(8) -0.028(6) O6 0.067(6) 0.082(8) 0.231(18) -0.016(10) -0.038(9) -0.020(6) F1 0.43(4) 0.070(8) 0.70(7) 0.000 -0.16(4) 0.000 F2 0.119(7) 0.090(7) 0.137(11) -0.090(8) 0.002(7) -0.001(6) F3 0.114(7) 0.085(6) 0.120(7) 0.014(5) -0.003(6) 0.057(5) Cl 0.0401(7) 0.0641(10) 0.0468(8) 0.0089(10) 0.000 0.000 C1 0.0328(18) 0.0313(19) 0.028(2) 0.0046(15) -0.0024(19) 0.0047(18) C2 0.034(2) 0.041(2) 0.032(2) 0.0105(18) 0.0005(17) 0.0039(18) C3 0.051(2) 0.043(3) 0.033(2) 0.0062(19) -0.001(2) -0.011(2) C4 0.028(2) 0.050(3) 0.033(2) 0.0078(18) 0.0017(16) -0.0016(17) C7 0.039(2) 0.040(2) 0.033(2) 0.0125(19) -0.0012(19) -0.0040(19) C8 0.033(2) 0.036(2) 0.035(2) 0.0051(19) -0.0042(18) -0.0023(18) C9 0.056(3) 0.042(2) 0.039(3) 0.018(2) -0.001(2) -0.0050(19) C10 0.107(4) 0.046(3) 0.063(3) -0.002(3) 0.026(4) -0.012(3) C11 0.068(4) 0.070(4) 0.064(4) 0.004(3) 0.010(3) -0.014(3) C12 0.048(3) 0.040(3) 0.064(3) 0.006(2) 0.001(3) 0.005(2) N1 0.0419(17) 0.0467(19) 0.0351(17) 0.009(2) 0.0041(14) 0.010(2) N2 0.055(2) 0.041(2) 0.045(2) 0.0141(18) 0.0035(19) -0.0089(18) N3 0.051(2) 0.041(2) 0.039(2) -0.0007(17) -0.0069(17) -0.0050(17) N4 0.0337(17) 0.0353(18) 0.0307(17) 0.0070(14) 0.0025(16) 0.0063(16) O1 0.055(2) 0.057(2) 0.046(2) 0.0172(17) 0.0063(16) 0.0243(17) O2 0.065(2) 0.044(2) 0.100(3) 0.006(2) 0.012(2) 0.0148(18) O3 0.055(2) 0.0300(19) 0.110(4) 0.0092(19) 0.022(2) 0.0021(17) S1 0.0616(11) 0.0385(10) 0.0887(16) 0.000 0.0009(11) 0.000 Cu1 0.0454(4) 0.0429(4) 0.0262(3) 0.0065(3) 0.000 0.000 _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 C5 N2 1.450(6) . ? C5 C6 1.508(7) . ? C6 N3 1.452(6) . ? C13 C13 0.83(3) 3_655 ? C13 F1 0.868(14) . ? C13 F2 1.23(2) . ? C13 F3 1.258(15) . ? C13 F2 1.62(2) 3_655 ? C13 S1 1.831(14) . ? O4 O5 1.487(18) . ? O4 S1 1.519(10) . ? O4 O6 1.65(2) 3_655 ? O5 O6 1.166(17) . ? O5 S1 1.319(10) . ? O6 S1 1.365(10) . ? O6 O4 1.65(2) 3_655 ? F1 C13 0.868(14) 3_655 ? F1 F2 1.401(15) 3_655 ? F1 F2 1.401(15) . ? F1 F3 1.681(13) . ? F1 F3 1.681(13) 3_655 ? F2 C13 1.62(2) 3_655 ? C1 N4 1.471(5) . ? C1 C7 1.537(6) . ? C1 C3 1.539(6) 4_577 ? C1 C2 1.542(6) 4_577 ? C2 N1 1.477(5) . ? C2 C1 1.542(6) 4_577 ? C3 N2 1.475(6) . ? C3 C1 1.539(6) 4_577 ? C4 N1 1.450(5) . ? C4 C4 1.507(8) 4_577 ? C7 N3 1.467(6) . ? C8 O1 1.225(5) . ? C8 N4 1.345(5) . ? C8 C9 1.512(6) . ? C9 C10 1.559(7) . ? C10 C11 1.440(8) . ? C11 C12 1.483(8) . ? C12 O2 1.188(6) . ? C12 O3 1.311(6) . ? N1 Cu1 2.159(3) . ? N2 Cu1 2.189(4) . ? N3 Cu1 2.114(4) . ? S1 O5 1.319(10) 3_655 ? S1 O6 1.365(10) 3_655 ? S1 O4 1.519(10) 3_655 ? S1 C13 1.831(14) 3_655 ? Cu1 N3 2.114(4) 4_577 ? Cu1 N1 2.159(3) 4_577 ? Cu1 N2 2.189(4) 4_577 ? 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 C5 C6 109.6(4) . . ? N3 C6 C5 110.2(3) . . ? C13 C13 F1 61.4(12) 3_655 . ? C13 C13 F2 102(3) 3_655 . ? F1 C13 F2 81.7(16) . . ? C13 C13 F3 146(3) 3_655 . ? F1 C13 F3 103.0(11) . . ? F2 C13 F3 105.5(16) . . ? C13 C13 F2 48(2) 3_655 3_655 ? F1 C13 F2 59.8(13) . 3_655 ? F2 C13 F2 138.6(13) . 3_655 ? F3 C13 F2 98.1(13) . 3_655 ? C13 C13 S1 76.9(4) 3_655 . ? F1 C13 S1 138.3(15) . . ? F2 C13 S1 108.2(11) . . ? F3 C13 S1 112.4(10) . . ? F2 C13 S1 93.0(11) 3_655 . ? O5 O4 S1 52.0(5) . . ? O5 O4 O6 96.6(9) . 3_655 ? S1 O4 O6 50.9(6) . 3_655 ? O6 O5 S1 66.3(8) . . ? O6 O5 O4 124.6(10) . . ? S1 O5 O4 65.2(7) . . ? O5 O6 S1 62.3(8) . . ? O5 O6 O4 111.0(11) . 3_655 ? S1 O6 O4 59.7(7) . 3_655 ? C13 F1 C13 57(2) . 3_655 ? C13 F1 F2 87.8(18) . 3_655 ? C13 F1 F2 60.4(14) 3_655 3_655 ? C13 F1 F2 60.4(14) . . ? C13 F1 F2 87.8(18) 3_655 . ? F2 F1 F2 144.7(16) 3_655 . ? C13 F1 F3 46.8(8) . . ? C13 F1 F3 98.5(13) 3_655 . ? F2 F1 F3 89.9(8) 3_655 . ? F2 F1 F3 79.5(7) . . ? C13 F1 F3 98.5(13) . 3_655 ? C13 F1 F3 46.8(8) 3_655 3_655 ? F2 F1 F3 79.5(7) 3_655 3_655 ? F2 F1 F3 89.9(8) . 3_655 ? F3 F1 F3 144.4(12) . 3_655 ? C13 F2 F1 37.8(7) . . ? C13 F2 C13 30.2(10) . 3_655 ? F1 F2 C13 32.4(8) . 3_655 ? C13 F3 F1 30.2(7) . . ? N4 C1 C7 108.1(3) . . ? N4 C1 C3 104.8(3) . 4_577 ? C7 C1 C3 111.3(3) . 4_577 ? N4 C1 C2 108.7(3) . 4_577 ? C7 C1 C2 112.4(3) . 4_577 ? C3 C1 C2 111.1(3) 4_577 4_577 ? N1 C2 C1 113.6(3) . 4_577 ? N2 C3 C1 113.3(4) . 4_577 ? N1 C4 C4 110.0(3) . 4_577 ? N3 C7 C1 113.9(3) . . ? O1 C8 N4 122.1(4) . . ? O1 C8 C9 121.3(4) . . ? N4 C8 C9 116.6(4) . . ? C8 C9 C10 109.6(4) . . ? C11 C10 C9 116.7(5) . . ? C10 C11 C12 112.6(5) . . ? O2 C12 O3 123.4(5) . . ? O2 C12 C11 122.4(5) . . ? O3 C12 C11 114.1(5) . . ? C4 N1 C2 112.4(4) . . ? C4 N1 Cu1 108.0(3) . . ? C2 N1 Cu1 116.4(2) . . ? C5 N2 C3 113.6(4) . . ? C5 N2 Cu1 107.7(3) . . ? C3 N2 Cu1 117.0(3) . . ? C6 N3 C7 112.5(4) . . ? C6 N3 Cu1 110.7(3) . . ? C7 N3 Cu1 116.1(3) . . ? C8 N4 C1 125.7(4) . . ? O5 S1 O5 119.6(10) 3_655 . ? O5 S1 O6 121.6(8) 3_655 . ? O5 S1 O6 51.5(8) . . ? O5 S1 O6 51.5(8) 3_655 3_655 ? O5 S1 O6 121.6(8) . 3_655 ? O6 S1 O6 168.7(10) . 3_655 ? O5 S1 O4 110.5(8) 3_655 . ? O5 S1 O4 62.7(7) . . ? O6 S1 O4 109.3(10) . . ? O6 S1 O4 69.4(10) 3_655 . ? O5 S1 O4 62.7(7) 3_655 3_655 ? O5 S1 O4 110.5(8) . 3_655 ? O6 S1 O4 69.4(10) . 3_655 ? O6 S1 O4 109.3(10) 3_655 3_655 ? O4 S1 O4 167.6(8) . 3_655 ? O5 S1 C13 107.8(7) 3_655 3_655 ? O5 S1 C13 132.4(7) . 3_655 ? O6 S1 C13 107.2(7) . 3_655 ? O6 S1 C13 84.0(6) 3_655 3_655 ? O4 S1 C13 97.7(8) . 3_655 ? O4 S1 C13 94.3(8) 3_655 3_655 ? O5 S1 C13 132.4(7) 3_655 . ? O5 S1 C13 107.8(7) . . ? O6 S1 C13 84.0(6) . . ? O6 S1 C13 107.2(7) 3_655 . ? O4 S1 C13 94.3(8) . . ? O4 S1 C13 97.7(8) 3_655 . ? C13 S1 C13 26.3(8) 3_655 . ? N3 Cu1 N3 157.7(2) . 4_577 ? N3 Cu1 N1 85.71(15) . 4_577 ? N3 Cu1 N1 111.71(17) 4_577 4_577 ? N3 Cu1 N1 111.71(17) . . ? N3 Cu1 N1 85.71(15) 4_577 . ? N1 Cu1 N1 80.82(18) 4_577 . ? N3 Cu1 N2 80.25(14) . . ? N3 Cu1 N2 88.11(15) 4_577 . ? N1 Cu1 N2 153.91(15) 4_577 . ? N1 Cu1 N2 84.09(15) . . ? N3 Cu1 N2 88.11(15) . 4_577 ? N3 Cu1 N2 80.25(14) 4_577 4_577 ? N1 Cu1 N2 84.09(15) 4_577 4_577 ? N1 Cu1 N2 153.91(15) . 4_577 ? N2 Cu1 N2 117.1(2) . 4_577 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.541 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.069