# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Donnelly, Paul' _publ_contact_author_name 'Donnelly, Paul' _publ_contact_author_email pauld@unimelb.edu.au _publ_section_title ; Copper(II) complexes of hybrid hydroxyquinoline-thiosemicarbazone ligands: GSK3b inhibition due to intracellular delivery of copper ; data_jmwpd139a _database_code_depnum_ccdc_archive 'CCDC 801975' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 Cu N4 O2 S' _chemical_formula_weight 353.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P -1' _symmetry_cell_setting triclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9196(7) _cell_length_b 9.5097(10) _cell_length_c 10.0744(11) _cell_angle_alpha 91.711(9) _cell_angle_beta 90.001(8) _cell_angle_gamma 111.220(9) _cell_volume 706.93(12) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2977 _cell_measurement_theta_min 4.3873 _cell_measurement_theta_max 73.3400 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.2006 _exptl_crystal_size_mid 0.1135 _exptl_crystal_size_min 0.0200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 3.655 _exptl_absorpt_correction_T_min 0.000 _exptl_absorpt_correction_T_max 0.930 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4732 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.39 _diffrn_reflns_theta_max 73.50 _reflns_number_total 2735 _reflns_number_gt 2185 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _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^)+(0.0823P)^2^+1.1077P] 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 2735 _refine_ls_number_parameters 196 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1339 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.143 _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 1.2232(6) 0.5354(5) 0.2563(5) 0.0321(9) Uani 1 1 d . . . C2 C 1.3518(6) 0.4898(5) 0.3220(4) 0.0327(9) Uani 1 1 d . . . H2 H 1.4736 0.5302 0.2997 0.039 Uiso 1 1 calc R . . C3 C 1.2945(6) 0.3849(5) 0.4195(4) 0.0330(9) Uani 1 1 d . . . H3 H 1.3794 0.3554 0.4629 0.040 Uiso 1 1 calc R . . C4 C 1.1108(6) 0.3208(5) 0.4555(4) 0.0324(9) Uani 1 1 d . . . C5 C 0.9903(6) 0.3719(5) 0.3854(4) 0.0318(9) Uani 1 1 d . . . C6 C 0.8000(6) 0.3188(5) 0.4019(4) 0.0300(9) Uani 1 1 d . . . C7 C 0.7308(6) 0.2080(5) 0.4933(5) 0.0352(10) Uani 1 1 d . . . H7 H 0.6067 0.1680 0.5078 0.042 Uiso 1 1 calc R . . C8 C 0.8483(7) 0.1546(5) 0.5655(5) 0.0378(10) Uani 1 1 d . . . H8 H 0.7980 0.0796 0.6264 0.045 Uiso 1 1 calc R . . C9 C 1.0330(7) 0.2087(5) 0.5496(5) 0.0363(10) Uani 1 1 d . . . H9 H 1.1057 0.1720 0.5999 0.044 Uiso 1 1 calc R . . C10 C 1.2475(6) 0.6404(5) 0.1482(4) 0.0318(9) Uani 1 1 d . . . H10 H 1.3593 0.6920 0.1107 0.038 Uiso 1 1 calc R . . C11 C 0.9282(6) 0.7391(5) -0.0167(4) 0.0328(9) Uani 1 1 d . . . C12 C 1.0551(6) 0.9340(6) -0.1806(5) 0.0397(11) Uani 1 1 d . . . H12A H 1.0086 0.9862 -0.2426 0.060 Uiso 1 1 calc R . . H12B H 1.1209 0.8814 -0.2277 0.060 Uiso 1 1 calc R . . H12C H 1.1344 1.0055 -0.1179 0.060 Uiso 1 1 calc R . . C13 C 0.4698(7) 0.0533(6) 0.1687(6) 0.0490(13) Uani 1 1 d . . . H13A H 0.5696 0.1081 0.1138 0.073 Uiso 1 1 calc R . . H13B H 0.3756 -0.0173 0.1145 0.073 Uiso 1 1 calc R . . H13C H 0.5100 -0.0002 0.2334 0.073 Uiso 1 1 calc R . . O1 O 0.7051(4) 0.3772(4) 0.3247(3) 0.0335(7) Uani 1 1 d . . . O2 O 0.4025(4) 0.1553(4) 0.2342(4) 0.0414(8) Uani 1 1 d D . . S1 S 0.72910(14) 0.62798(13) 0.06489(11) 0.0332(3) Uani 1 1 d . . . Cu1 Cu 0.87265(8) 0.52763(7) 0.20088(6) 0.0298(2) Uani 1 1 d . . . N1 N 1.0505(5) 0.4745(4) 0.2919(4) 0.0285(7) Uani 1 1 d . . . N2 N 1.0982(5) 0.6545(4) 0.1096(4) 0.0315(8) Uani 1 1 d . . . N3 N 1.0962(5) 0.7447(4) 0.0073(4) 0.0323(8) Uani 1 1 d . . . N4 N 0.9061(5) 0.8268(4) -0.1109(4) 0.0354(8) Uani 1 1 d . . . H4 H 0.7977 0.8193 -0.1313 0.042 Uiso 1 1 calc R . . H H 0.501(7) 0.231(7) 0.250(10) 0.12(3) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0246(19) 0.035(2) 0.036(2) 0.0042(19) -0.0030(17) 0.0100(17) C2 0.026(2) 0.038(2) 0.034(2) 0.0033(19) -0.0007(17) 0.0119(18) C3 0.033(2) 0.038(2) 0.031(2) 0.0019(19) -0.0045(17) 0.0177(19) C4 0.033(2) 0.037(2) 0.030(2) 0.0052(18) -0.0022(17) 0.0157(18) C5 0.031(2) 0.036(2) 0.028(2) 0.0012(19) -0.0022(17) 0.0130(18) C6 0.033(2) 0.035(2) 0.025(2) 0.0018(17) 0.0004(16) 0.0161(18) C7 0.028(2) 0.042(3) 0.035(2) 0.006(2) 0.0036(18) 0.0115(19) C8 0.044(2) 0.039(3) 0.034(2) 0.013(2) 0.0043(19) 0.019(2) C9 0.041(2) 0.040(3) 0.034(2) 0.010(2) 0.0022(19) 0.021(2) C10 0.0236(19) 0.034(2) 0.035(2) 0.0059(19) -0.0006(16) 0.0069(17) C11 0.033(2) 0.039(2) 0.028(2) 0.0056(19) -0.0020(17) 0.0148(19) C12 0.036(2) 0.045(3) 0.038(2) 0.015(2) 0.0001(19) 0.014(2) C13 0.036(3) 0.050(3) 0.057(3) -0.003(3) 0.004(2) 0.011(2) O1 0.0276(15) 0.0410(17) 0.0345(16) 0.0111(14) 0.0023(12) 0.0149(13) O2 0.0322(17) 0.046(2) 0.049(2) 0.0058(16) -0.0020(15) 0.0171(15) S1 0.0257(5) 0.0403(6) 0.0354(6) 0.0115(5) -0.0006(4) 0.0135(4) Cu1 0.0248(3) 0.0363(4) 0.0300(4) 0.0086(3) -0.0002(2) 0.0125(3) N1 0.0240(16) 0.0288(18) 0.0332(18) 0.0028(15) -0.0034(14) 0.0101(14) N2 0.0262(17) 0.037(2) 0.0310(18) 0.0095(16) 0.0002(14) 0.0108(15) N3 0.0277(17) 0.037(2) 0.0318(19) 0.0106(16) 0.0001(14) 0.0101(15) N4 0.0317(18) 0.043(2) 0.0342(19) 0.0109(17) -0.0020(15) 0.0165(17) _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 1.332(5) . ? C1 C2 1.414(6) . ? C1 C10 1.465(6) . ? C2 C3 1.377(6) . ? C2 H2 0.9300 . ? C3 C4 1.411(6) . ? C3 H3 0.9300 . ? C4 C5 1.414(6) . ? C4 C9 1.414(6) . ? C5 N1 1.336(6) . ? C5 C6 1.418(6) . ? C6 O1 1.344(5) . ? C6 C7 1.378(6) . ? C7 C8 1.420(6) . ? C7 H7 0.9300 . ? C8 C9 1.375(7) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 N2 1.298(5) . ? C10 H10 0.9300 . ? C11 N3 1.334(6) . ? C11 N4 1.334(6) . ? C11 S1 1.767(5) . ? C12 N4 1.448(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O2 1.413(6) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? O1 Cu1 2.024(3) . ? O2 H 0.86(7) . ? S1 Cu1 2.2234(11) . ? Cu1 N1 1.903(3) . ? Cu1 N2 1.999(4) . ? N2 N3 1.364(5) . ? N4 H4 0.8600 . ? 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 118.2(4) . . ? N1 C1 C10 111.9(4) . . ? C2 C1 C10 129.9(4) . . ? C3 C2 C1 119.2(4) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 121.9(4) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C3 C4 C5 115.7(4) . . ? C3 C4 C9 127.7(4) . . ? C5 C4 C9 116.6(4) . . ? N1 C5 C4 121.0(4) . . ? N1 C5 C6 113.9(4) . . ? C4 C5 C6 125.1(4) . . ? O1 C6 C7 126.7(4) . . ? O1 C6 C5 117.3(4) . . ? C7 C6 C5 115.9(4) . . ? C6 C7 C8 120.3(4) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 123.1(4) . . ? C9 C8 H8 118.5 . . ? C7 C8 H8 118.5 . . ? C8 C9 C4 119.0(4) . . ? C8 C9 H9 120.5 . . ? C4 C9 H9 120.5 . . ? N2 C10 C1 113.7(4) . . ? N2 C10 H10 123.2 . . ? C1 C10 H10 123.2 . . ? N3 C11 N4 117.4(4) . . ? N3 C11 S1 126.7(3) . . ? N4 C11 S1 115.8(3) . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C6 O1 Cu1 110.3(2) . . ? C13 O2 H 101(7) . . ? C11 S1 Cu1 94.36(14) . . ? N1 Cu1 N2 78.98(15) . . ? N1 Cu1 O1 81.89(14) . . ? N2 Cu1 O1 160.86(13) . . ? N1 Cu1 S1 164.66(12) . . ? N2 Cu1 S1 85.68(11) . . ? O1 Cu1 S1 113.45(9) . . ? C1 N1 C5 124.1(4) . . ? C1 N1 Cu1 119.2(3) . . ? C5 N1 Cu1 116.6(3) . . ? C10 N2 N3 121.2(4) . . ? C10 N2 Cu1 116.2(3) . . ? N3 N2 Cu1 122.5(3) . . ? C11 N3 N2 110.7(4) . . ? C11 N4 C12 123.5(4) . . ? C11 N4 H4 118.3 . . ? C12 N4 H4 118.3 . . ? 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 C1 C2 C3 0.1(7) . . . . ? C10 C1 C2 C3 -178.1(5) . . . . ? C1 C2 C3 C4 0.3(7) . . . . ? C2 C3 C4 C5 -0.3(7) . . . . ? C2 C3 C4 C9 177.4(5) . . . . ? C3 C4 C5 N1 -0.1(7) . . . . ? C9 C4 C5 N1 -178.1(4) . . . . ? C3 C4 C5 C6 177.6(4) . . . . ? C9 C4 C5 C6 -0.4(7) . . . . ? N1 C5 C6 O1 -0.5(6) . . . . ? C4 C5 C6 O1 -178.4(4) . . . . ? N1 C5 C6 C7 177.3(4) . . . . ? C4 C5 C6 C7 -0.5(7) . . . . ? O1 C6 C7 C8 178.2(4) . . . . ? C5 C6 C7 C8 0.7(7) . . . . ? C6 C7 C8 C9 0.2(8) . . . . ? C7 C8 C9 C4 -1.2(8) . . . . ? C3 C4 C9 C8 -176.5(5) . . . . ? C5 C4 C9 C8 1.2(7) . . . . ? N1 C1 C10 N2 0.6(6) . . . . ? C2 C1 C10 N2 178.9(5) . . . . ? C7 C6 O1 Cu1 -176.6(4) . . . . ? C5 C6 O1 Cu1 0.9(5) . . . . ? N3 C11 S1 Cu1 0.8(4) . . . . ? N4 C11 S1 Cu1 -178.5(4) . . . . ? C6 O1 Cu1 N1 -0.8(3) . . . . ? C6 O1 Cu1 N2 1.4(6) . . . . ? C6 O1 Cu1 S1 178.8(3) . . . . ? C11 S1 Cu1 N1 -0.4(5) . . . . ? C11 S1 Cu1 N2 0.42(18) . . . . ? C11 S1 Cu1 O1 -178.72(18) . . . . ? C2 C1 N1 C5 -0.5(7) . . . . ? C10 C1 N1 C5 178.0(4) . . . . ? C2 C1 N1 Cu1 -177.7(3) . . . . ? C10 C1 N1 Cu1 0.8(5) . . . . ? C4 C5 N1 C1 0.5(7) . . . . ? C6 C5 N1 C1 -177.4(4) . . . . ? C4 C5 N1 Cu1 177.7(3) . . . . ? C6 C5 N1 Cu1 -0.2(5) . . . . ? N2 Cu1 N1 C1 -1.4(3) . . . . ? O1 Cu1 N1 C1 177.9(4) . . . . ? S1 Cu1 N1 C1 -0.5(7) . . . . ? N2 Cu1 N1 C5 -178.7(4) . . . . ? O1 Cu1 N1 C5 0.5(3) . . . . ? S1 Cu1 N1 C5 -177.9(3) . . . . ? C1 C10 N2 N3 -178.2(4) . . . . ? C1 C10 N2 Cu1 -1.8(5) . . . . ? N1 Cu1 N2 C10 1.7(3) . . . . ? O1 Cu1 N2 C10 -0.4(7) . . . . ? S1 Cu1 N2 C10 -178.0(3) . . . . ? N1 Cu1 N2 N3 178.1(4) . . . . ? O1 Cu1 N2 N3 175.9(4) . . . . ? S1 Cu1 N2 N3 -1.7(3) . . . . ? N4 C11 N3 N2 177.3(4) . . . . ? S1 C11 N3 N2 -2.0(6) . . . . ? C10 N2 N3 C11 178.6(4) . . . . ? Cu1 N2 N3 C11 2.4(5) . . . . ? N3 C11 N4 C12 -4.5(7) . . . . ? S1 C11 N4 C12 174.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 73.50 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.595 _refine_diff_density_min -0.849 _refine_diff_density_rms 0.119 data_jmwpd34 _database_code_depnum_ccdc_archive 'CCDC 801976' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 N4 O S' _chemical_formula_weight 260.32 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' _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 10.3943(12) _cell_length_b 7.0021(8) _cell_length_c 16.770(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.544(2) _cell_angle_gamma 90.00 _cell_volume 1207.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1720 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.27 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.86 _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 6094 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2118 _reflns_number_gt 1807 _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. ; _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^)+(0.0511P)^2^+0.4102P] 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 2118 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 1.034 _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 C1 C 0.38722(18) 0.1850(3) 0.20613(12) 0.0228(5) Uani 1 1 d . . . C2 C 0.2751(2) 0.1126(3) 0.22760(13) 0.0275(5) Uani 1 1 d . . . H2 H 0.2671 0.0973 0.2817 0.033 Uiso 1 1 calc R . . C3 C 0.1720(2) 0.0614(3) 0.16742(14) 0.0292(5) Uani 1 1 d . . . H3 H 0.0956 0.0140 0.1825 0.035 Uiso 1 1 calc R . . C4 C 0.18097(19) 0.0795(3) 0.08709(13) 0.0269(5) Uani 1 1 d . . . H4 H 0.1107 0.0467 0.0485 0.032 Uiso 1 1 calc R . . C5 C 0.29760(18) 0.1482(3) 0.06287(12) 0.0216(4) Uani 1 1 d . . . C6 C 0.32002(18) 0.1672(3) -0.01837(12) 0.0226(4) Uani 1 1 d . . . H6 H 0.2542 0.1377 -0.0604 0.027 Uiso 1 1 calc R . . C7 C 0.43772(18) 0.2286(3) -0.03468(12) 0.0214(4) Uani 1 1 d . . . H7 H 0.4533 0.2394 -0.0877 0.026 Uiso 1 1 calc R . . C8 C 0.53603(17) 0.2757(2) 0.03020(11) 0.0178(4) Uani 1 1 d . . . C9 C 0.40123(18) 0.2012(3) 0.12294(12) 0.0194(4) Uani 1 1 d . . . C10 C 0.66704(18) 0.3348(3) 0.01845(11) 0.0197(4) Uani 1 1 d . . . H10 H 0.7287 0.3604 0.0633 0.024 Uiso 1 1 calc R . . C11 C 0.86866(19) 0.4201(3) -0.12695(12) 0.0203(4) Uani 1 1 d . . . C12 C 0.8093(2) 0.4235(3) -0.27406(12) 0.0271(5) Uani 1 1 d . . . H12A H 0.7306 0.4091 -0.3115 0.041 Uiso 1 1 calc R . . H12B H 0.8699 0.3256 -0.2835 0.041 Uiso 1 1 calc R . . H12C H 0.8466 0.5466 -0.2812 0.041 Uiso 1 1 calc R . . N1 N 0.51841(14) 0.2659(2) 0.10711(9) 0.0190(4) Uani 1 1 d . . . N3 N 0.69874(15) 0.3522(2) -0.05228(10) 0.0201(4) Uani 1 1 d . . . N4 N 0.82569(16) 0.3988(2) -0.05451(10) 0.0211(4) Uani 1 1 d . . . N5 N 0.78011(16) 0.4070(2) -0.19204(10) 0.0214(4) Uani 1 1 d . . . O1 O 0.48743(14) 0.2444(2) 0.26279(9) 0.0300(4) Uani 1 1 d . . . S1 S 1.02878(5) 0.45630(8) -0.12907(3) 0.02712(18) Uani 1 1 d . . . H H 0.540(3) 0.295(4) 0.2374(16) 0.055(9) Uiso 1 1 d . . . H4A H 0.877(2) 0.421(3) -0.0102(14) 0.028(6) Uiso 1 1 d . . . H5 H 0.697(2) 0.395(3) -0.1862(14) 0.039(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0248(11) 0.0203(10) 0.0253(11) -0.0001(9) 0.0100(9) 0.0021(8) C2 0.0329(12) 0.0231(11) 0.0301(12) 0.0036(9) 0.0168(10) 0.0030(9) C3 0.0255(11) 0.0223(11) 0.0441(14) 0.0009(10) 0.0189(10) -0.0007(8) C4 0.0188(10) 0.0243(11) 0.0381(13) -0.0018(10) 0.0057(9) -0.0002(8) C5 0.0203(10) 0.0161(10) 0.0296(11) -0.0012(9) 0.0071(8) 0.0028(8) C6 0.0212(10) 0.0208(10) 0.0246(11) -0.0033(9) -0.0004(8) 0.0018(8) C7 0.0263(11) 0.0202(10) 0.0184(10) 0.0003(8) 0.0049(8) 0.0019(8) C8 0.0199(10) 0.0136(9) 0.0207(10) 0.0023(8) 0.0057(8) 0.0025(7) C9 0.0204(10) 0.0140(9) 0.0256(11) 0.0012(8) 0.0093(8) 0.0034(8) C10 0.0211(10) 0.0184(10) 0.0198(10) 0.0006(8) 0.0038(8) -0.0004(8) C11 0.0237(11) 0.0180(10) 0.0209(10) -0.0007(8) 0.0089(8) 0.0007(8) C12 0.0282(11) 0.0362(12) 0.0177(10) -0.0003(9) 0.0063(8) -0.0041(9) N1 0.0189(8) 0.0185(8) 0.0202(9) 0.0013(7) 0.0054(7) 0.0012(7) N3 0.0196(8) 0.0195(9) 0.0227(9) 0.0004(7) 0.0084(7) 0.0005(7) N4 0.0178(9) 0.0275(9) 0.0190(9) -0.0005(7) 0.0056(7) -0.0019(7) N5 0.0190(9) 0.0270(9) 0.0190(9) 0.0002(7) 0.0058(7) -0.0011(7) O1 0.0307(8) 0.0400(9) 0.0205(8) 0.0005(7) 0.0078(7) -0.0059(7) S1 0.0187(3) 0.0414(3) 0.0227(3) -0.0031(2) 0.0079(2) -0.0041(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 C1 O1 1.366(2) . ? C1 C2 1.368(3) . ? C1 C9 1.429(3) . ? C2 C3 1.405(3) . ? C3 C4 1.370(3) . ? C4 C5 1.419(3) . ? C5 C9 1.411(3) . ? C5 C6 1.422(3) . ? C6 C7 1.362(3) . ? C7 C8 1.416(3) . ? C8 N1 1.331(2) . ? C8 C10 1.464(2) . ? C9 N1 1.362(2) . ? C10 N3 1.283(2) . ? C11 N5 1.322(3) . ? C11 N4 1.363(2) . ? C11 S1 1.6891(19) . ? C12 N5 1.456(2) . ? N3 N4 1.365(2) . ? 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 O1 C1 C2 121.42(19) . . ? O1 C1 C9 118.51(16) . . ? C2 C1 C9 120.07(19) . . ? C1 C2 C3 119.6(2) . . ? C4 C3 C2 121.82(18) . . ? C3 C4 C5 119.9(2) . . ? C9 C5 C4 118.62(19) . . ? C9 C5 C6 116.31(16) . . ? C4 C5 C6 125.07(19) . . ? C7 C6 C5 120.11(18) . . ? C6 C7 C8 119.09(18) . . ? N1 C8 C7 123.01(16) . . ? N1 C8 C10 114.17(17) . . ? C7 C8 C10 122.80(17) . . ? N1 C9 C5 123.93(18) . . ? N1 C9 C1 116.14(17) . . ? C5 C9 C1 119.92(17) . . ? N3 C10 C8 121.52(18) . . ? N5 C11 N4 116.61(17) . . ? N5 C11 S1 124.07(15) . . ? N4 C11 S1 119.31(15) . . ? C8 N1 C9 117.50(16) . . ? C10 N3 N4 115.47(16) . . ? C11 N4 N3 119.77(17) . . ? C11 N5 C12 123.85(16) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.250 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.049 data_jmwpd44 _database_code_depnum_ccdc_archive 'CCDC 801977' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 Cu N4 O2 S' _chemical_formula_weight 401.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M P212121 _symmetry_cell_setting orthorhombic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.0657(2) _cell_length_b 14.7702(8) _cell_length_c 26.2659(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1577.30(13) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2655 _cell_measurement_theta_min 2.9885 _cell_measurement_theta_max 72.8338 _exptl_crystal_description rod _exptl_crystal_colour black _exptl_crystal_size_max 0.4602 _exptl_crystal_size_mid 0.0611 _exptl_crystal_size_min 0.0600 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 3.367 _exptl_absorpt_correction_T_min 0.35833 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _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 4906 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 73.41 _reflns_number_total 2707 _reflns_number_gt 2411 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _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^)+(0.0665P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(4) _refine_ls_number_reflns 2707 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.002 _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 C2 C -0.1513(13) 0.7179(3) 0.31894(14) 0.0257(8) Uani 1 1 d . . . C3 C -0.3334(14) 0.6612(3) 0.35206(16) 0.0303(9) Uani 1 1 d . . . H3 H -0.3781 0.6017 0.3428 0.036 Uiso 1 1 calc R . . C4 C -0.4438(13) 0.6940(3) 0.39781(16) 0.0342(11) Uani 1 1 d . . . H4 H -0.5614 0.6564 0.4196 0.041 Uiso 1 1 calc R . . C5 C -0.3800(14) 0.7848(3) 0.41205(14) 0.0301(10) Uani 1 1 d . . . C6 C -0.4741(15) 0.8273(4) 0.45823(16) 0.0400(12) Uani 1 1 d . . . H6 H -0.5897 0.7951 0.4828 0.048 Uiso 1 1 calc R . . C7 C -0.3931(16) 0.9159(3) 0.46619(15) 0.0397(12) Uani 1 1 d . . . H7 H -0.4564 0.9428 0.4967 0.048 Uiso 1 1 calc R . . C8 C -0.2208(13) 0.9680(3) 0.43098(15) 0.0349(11) Uani 1 1 d . . . H8 H -0.1715 1.0280 0.4384 0.042 Uiso 1 1 calc R . . C9 C -0.1215(13) 0.9306(3) 0.38467(14) 0.0275(9) Uani 1 1 d . . . C10 C -0.1988(12) 0.8374(3) 0.37647(15) 0.0270(9) Uani 1 1 d . . . C11 C -0.0270(12) 0.6793(3) 0.27061(14) 0.0278(9) Uani 1 1 d . . . H11 H -0.0971 0.6208 0.2633 0.033 Uiso 1 1 calc R . . C12 C 0.4757(11) 0.8421(3) 0.21259(14) 0.0223(8) Uani 1 1 d . . . C13 C 0.8041(11) 0.8316(3) 0.13220(14) 0.0237(8) Uani 1 1 d . . . C14 C 0.8990(14) 0.7665(3) 0.09696(14) 0.0307(10) Uani 1 1 d . . . H14 H 0.8339 0.7066 0.1011 0.037 Uiso 1 1 calc R . . C15 C 1.0916(14) 0.7913(3) 0.05545(15) 0.0344(11) Uani 1 1 d . . . H15 H 1.1598 0.7476 0.0323 0.041 Uiso 1 1 calc R . . C16 C 1.1817(13) 0.8803(3) 0.04854(14) 0.0348(11) Uani 1 1 d . . . H16 H 1.3022 0.8973 0.0200 0.042 Uiso 1 1 calc R . . C17 C 1.0914(14) 0.9441(3) 0.08436(14) 0.0330(10) Uani 1 1 d . . . H17 H 1.1598 1.0037 0.0803 0.040 Uiso 1 1 calc R . . C18 C 0.9000(12) 0.9211(3) 0.12650(14) 0.0277(9) Uani 1 1 d . . . H18 H 0.8382 0.9647 0.1502 0.033 Uiso 1 1 calc R . . N1 N -0.0945(10) 0.8032(2) 0.33159(11) 0.0237(7) Uani 1 1 d . . . N2 N 0.1665(10) 0.7158(2) 0.23702(12) 0.0264(7) Uani 1 1 d . . . N3 N 0.2664(10) 0.8028(2) 0.24518(12) 0.0242(8) Uani 1 1 d . . . N4 N 0.5968(11) 0.8007(2) 0.17224(13) 0.0238(8) Uani 1 1 d . . . O1 O 0.0390(9) 0.9752(2) 0.34822(10) 0.0289(7) Uani 1 1 d . . . O2 O 0.5012(12) 0.6115(3) 0.15301(17) 0.0447(9) Uani 1 1 d . . . S1 S 0.5498(3) 0.95208(7) 0.23513(3) 0.0249(2) Uani 1 1 d . . . Cu1 Cu 0.14426(17) 0.89414(4) 0.29256(2) 0.02512(18) Uani 1 1 d . . . H H 0.565(15) 0.759(3) 0.1701(17) 0.018(14) Uiso 1 1 d . . . H2A H 0.65(3) 0.585(6) 0.148(3) 0.08(3) Uiso 1 1 d . . . H2B H 0.33(4) 0.593(9) 0.160(4) 0.18(6) 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 C2 0.024(2) 0.0279(18) 0.0256(18) 0.0016(16) -0.0064(18) 0.001(2) C3 0.031(2) 0.0251(18) 0.035(2) 0.0039(16) -0.003(2) 0.000(2) C4 0.028(3) 0.041(2) 0.034(2) 0.0193(19) 0.003(2) -0.001(2) C5 0.028(3) 0.038(2) 0.0238(18) 0.0077(17) 0.0010(19) 0.005(2) C6 0.043(3) 0.054(3) 0.0234(19) 0.012(2) 0.008(2) 0.014(3) C7 0.046(3) 0.053(3) 0.0203(17) -0.0008(19) 0.007(2) 0.017(3) C8 0.040(3) 0.040(2) 0.025(2) -0.0041(18) -0.0011(19) 0.006(2) C9 0.028(2) 0.035(2) 0.0202(17) -0.0014(15) -0.0019(18) 0.005(2) C10 0.026(2) 0.035(2) 0.0197(18) 0.0045(16) -0.0022(17) 0.0064(19) C11 0.033(3) 0.0237(17) 0.0262(18) -0.0024(16) -0.0043(19) -0.0007(18) C12 0.024(2) 0.0246(16) 0.0184(16) -0.0037(15) -0.0071(17) 0.0031(16) C13 0.021(2) 0.0323(19) 0.0176(16) 0.0024(16) -0.0052(16) 0.0026(18) C14 0.032(3) 0.036(2) 0.0241(18) -0.0033(17) -0.0033(19) 0.001(2) C15 0.032(3) 0.047(2) 0.0249(18) -0.0082(18) -0.002(2) 0.007(2) C16 0.034(3) 0.052(3) 0.0186(17) 0.0009(17) 0.0028(18) 0.001(2) C17 0.039(3) 0.036(2) 0.0244(18) 0.0050(17) -0.006(2) -0.004(2) C18 0.030(2) 0.0324(19) 0.0209(17) -0.0029(15) -0.0041(18) 0.002(2) N1 0.0214(19) 0.0299(16) 0.0198(14) 0.0018(12) -0.0032(14) 0.0056(16) N2 0.0272(19) 0.0267(15) 0.0253(15) -0.0048(14) -0.0030(16) 0.0022(16) N3 0.029(2) 0.0239(14) 0.0196(15) -0.0005(12) -0.0060(14) 0.0008(14) N4 0.027(2) 0.0220(16) 0.0228(16) -0.0031(14) -0.0042(15) 0.0003(17) O1 0.036(2) 0.0289(14) 0.0215(12) -0.0021(11) 0.0035(13) -0.0007(14) O2 0.039(2) 0.0285(16) 0.067(2) -0.0100(17) 0.011(2) -0.0004(19) S1 0.0284(6) 0.0243(4) 0.0220(4) -0.0029(4) 0.0006(4) -0.0014(4) Cu1 0.0311(3) 0.0239(3) 0.0204(3) -0.0022(2) 0.0030(3) -0.0012(3) _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 C2 N1 1.323(5) . ? C2 C3 1.416(6) . ? C2 C11 1.481(6) . ? C3 C4 1.371(6) . ? C4 C5 1.417(6) . ? C5 C6 1.418(6) . ? C5 C10 1.421(6) . ? C6 C7 1.366(7) . ? C7 C8 1.392(7) . ? C8 C9 1.396(6) . ? C9 O1 1.333(5) . ? C9 C10 1.427(6) . ? C10 N1 1.351(5) . ? C11 N2 1.299(6) . ? C12 N4 1.319(5) . ? C12 N3 1.339(6) . ? C12 S1 1.755(4) . ? C13 C18 1.387(6) . ? C13 C14 1.388(6) . ? C13 N4 1.423(6) . ? C14 C15 1.391(7) . ? C15 C16 1.376(6) . ? C16 C17 1.381(6) . ? C17 C18 1.395(6) . ? N1 Cu1 1.949(4) . ? N2 N3 1.365(4) . ? N3 Cu1 1.901(3) . ? O1 Cu1 1.937(3) . ? S1 Cu1 2.3930(12) . ? 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 C2 C3 120.0(4) . . ? N1 C2 C11 121.5(4) . . ? C3 C2 C11 118.5(4) . . ? C4 C3 C2 120.0(4) . . ? C3 C4 C5 120.4(4) . . ? C4 C5 C6 126.5(4) . . ? C4 C5 C10 116.0(4) . . ? C6 C5 C10 117.4(4) . . ? C7 C6 C5 119.3(4) . . ? C6 C7 C8 123.3(4) . . ? C7 C8 C9 120.4(4) . . ? O1 C9 C8 124.9(4) . . ? O1 C9 C10 118.4(4) . . ? C8 C9 C10 116.7(4) . . ? N1 C10 C5 122.1(4) . . ? N1 C10 C9 115.0(4) . . ? C5 C10 C9 122.8(4) . . ? N2 C11 C2 129.0(4) . . ? N4 C12 N3 123.4(4) . . ? N4 C12 S1 129.5(3) . . ? N3 C12 S1 107.1(3) . . ? C18 C13 C14 120.6(4) . . ? C18 C13 N4 123.5(4) . . ? C14 C13 N4 115.8(4) . . ? C13 C14 C15 119.8(4) . . ? C16 C15 C14 120.3(4) . . ? C15 C16 C17 119.4(4) . . ? C16 C17 C18 121.6(4) . . ? C13 C18 C17 118.3(4) . . ? C2 N1 C10 121.4(4) . . ? C2 N1 Cu1 127.7(3) . . ? C10 N1 Cu1 110.9(3) . . ? C11 N2 N3 117.7(3) . . ? C12 N3 N2 119.8(3) . . ? C12 N3 Cu1 106.1(3) . . ? N2 N3 Cu1 133.9(3) . . ? C12 N4 C13 131.8(4) . . ? C9 O1 Cu1 110.1(2) . . ? C12 S1 Cu1 76.31(14) . . ? N3 Cu1 O1 171.90(13) . . ? N3 Cu1 N1 89.17(15) . . ? O1 Cu1 N1 85.36(13) . . ? N3 Cu1 S1 70.19(11) . . ? O1 Cu1 S1 114.00(10) . . ? N1 Cu1 S1 157.13(11) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 73.41 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.756 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.112