# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jing-Min Shi' _publ_contact_author_email shijingmin1955@yahoo.com.cn _publ_author_name 'Jing-Min Shi' data_71129em _database_code_depnum_ccdc_archive 'CCDC 782938' #TrackingRef '- 71129em.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 Cu N3 O3 S' _chemical_formula_weight 380.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall ? 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 6.9794(15) _cell_length_b 22.703(5) _cell_length_c 10.259(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.843(3) _cell_angle_gamma 90.00 _cell_volume 1563.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2087 _cell_measurement_theta_min 2.250 _cell_measurement_theta_max 24.4095 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 1.548 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6373 _exptl_absorpt_correction_T_max 0.7898 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Bruker SMART APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9027 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3389 _reflns_number_gt 2547 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 2001)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0745P)^2^+0.7480P] 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 3389 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1399 _refine_ls_wR_factor_gt 0.1317 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 C1 C 0.5118(5) 0.15927(17) 0.8212(4) 0.0367(8) Uani 1 1 d . . . C2 C 0.6129(6) 0.21488(19) 0.8456(4) 0.0463(10) Uani 1 1 d . . . H2 H 0.7486 0.2155 0.8888 0.056 Uiso 1 1 calc R . . C3 C 0.5178(6) 0.26611(18) 0.8081(4) 0.0480(10) Uani 1 1 d . . . H3 H 0.5862 0.3017 0.8259 0.058 Uiso 1 1 calc R . . C4 C 0.3117(6) 0.26510(16) 0.7410(4) 0.0382(8) Uani 1 1 d . . . C5 C 0.2195(5) 0.21043(15) 0.7187(3) 0.0308(7) Uani 1 1 d . . . C6 C 0.0117(5) 0.20733(14) 0.6507(3) 0.0295(7) Uani 1 1 d . . . C7 C -0.2616(5) 0.14746(17) 0.5641(4) 0.0388(9) Uani 1 1 d . . . H7 H -0.3187 0.1102 0.5499 0.047 Uiso 1 1 calc R . . C8 C -0.3791(6) 0.19659(19) 0.5156(4) 0.0464(10) Uani 1 1 d . . . H8 H -0.5123 0.1916 0.4686 0.056 Uiso 1 1 calc R . . C9 C -0.3014(6) 0.25174(19) 0.5363(4) 0.0467(10) Uani 1 1 d . . . H9 H -0.3807 0.2844 0.5041 0.056 Uiso 1 1 calc R . . C10 C -0.0990(5) 0.25887(16) 0.6071(4) 0.0367(8) Uani 1 1 d . . . C11 C 0.1965(7) 0.31660(17) 0.6964(4) 0.0502(10) Uani 1 1 d . . . H11 H 0.2587 0.3532 0.7109 0.060 Uiso 1 1 calc R . . C12 C -0.0002(7) 0.31400(17) 0.6336(4) 0.0494(10) Uani 1 1 d . . . H12 H -0.0716 0.3486 0.6074 0.059 Uiso 1 1 calc R . . C13 C -0.1381(5) -0.01867(16) 0.6118(4) 0.0366(8) Uani 1 1 d . . . C14 C 0.0621(7) 0.0782(2) 1.0436(5) 0.0716(15) Uani 1 1 d . . . H14A H 0.1643 0.0502 1.0419 0.107 Uiso 1 1 calc R . . H14B H -0.0518 0.0580 1.0570 0.107 Uiso 1 1 calc R . . H14C H 0.1114 0.1055 1.1165 0.107 Uiso 1 1 calc R . . C15 C 0.3827(7) -0.0195(2) 0.7672(6) 0.0795(17) Uani 1 1 d . . . H15A H 0.2624 -0.0386 0.7169 0.119 Uiso 1 1 calc R . . H15B H 0.4477 -0.0434 0.8436 0.119 Uiso 1 1 calc R . . H15C H 0.4696 -0.0143 0.7099 0.119 Uiso 1 1 calc R . . Cu1 Cu 0.12587(6) 0.089527(18) 0.71265(5) 0.03659(18) Uani 1 1 d . . . N1 N 0.3131(4) 0.15828(12) 0.7591(3) 0.0316(6) Uani 1 1 d . . . N2 N -0.0699(4) 0.15262(12) 0.6301(3) 0.0320(6) Uani 1 1 d . . . N3 N -0.0599(5) 0.02487(14) 0.6536(3) 0.0444(8) Uani 1 1 d . . . O1 O 0.6072(4) 0.11097(13) 0.8594(3) 0.0536(8) Uani 1 1 d . . . H1 H 0.5345 0.0876 0.8838 0.080 Uiso 1 1 calc R . . O2 O 0.3364(4) 0.03586(12) 0.8128(3) 0.0502(7) Uani 1 1 d . . . O3 O 0.0084(4) 0.10824(14) 0.9228(3) 0.0523(7) Uani 1 1 d . . . H4 H -0.1134 0.1101 0.8958 0.078 Uiso 1 1 calc R . . S1 S -0.24674(18) -0.08014(5) 0.55155(13) 0.0560(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0293(18) 0.041(2) 0.0374(19) -0.0072(16) 0.0047(15) -0.0031(16) C2 0.0317(19) 0.056(3) 0.049(2) -0.014(2) 0.0083(17) -0.0140(19) C3 0.051(2) 0.041(2) 0.055(2) -0.0134(19) 0.020(2) -0.020(2) C4 0.047(2) 0.0322(19) 0.0381(19) -0.0059(16) 0.0158(17) -0.0124(17) C5 0.0342(18) 0.0273(17) 0.0328(18) -0.0024(14) 0.0124(14) -0.0008(15) C6 0.0323(18) 0.0267(16) 0.0317(17) -0.0015(14) 0.0126(14) -0.0014(14) C7 0.0309(18) 0.041(2) 0.041(2) -0.0034(17) 0.0045(16) -0.0036(16) C8 0.032(2) 0.061(3) 0.042(2) 0.0087(19) 0.0027(17) 0.0065(19) C9 0.045(2) 0.049(2) 0.045(2) 0.0109(19) 0.0101(18) 0.0151(19) C10 0.044(2) 0.0306(18) 0.040(2) 0.0015(15) 0.0182(17) 0.0040(16) C11 0.068(3) 0.0260(19) 0.062(3) -0.0023(18) 0.028(2) -0.0074(19) C12 0.064(3) 0.0262(18) 0.060(3) 0.0029(18) 0.019(2) 0.0051(19) C13 0.0316(18) 0.035(2) 0.043(2) 0.0007(16) 0.0094(16) 0.0003(16) C14 0.059(3) 0.077(4) 0.074(3) 0.009(3) 0.009(3) -0.007(3) C15 0.057(3) 0.034(2) 0.138(5) -0.006(3) 0.011(3) 0.014(2) Cu1 0.0281(3) 0.0224(2) 0.0535(3) -0.00276(19) 0.0014(2) -0.00150(17) N1 0.0267(13) 0.0293(15) 0.0364(15) -0.0049(13) 0.0048(12) -0.0017(12) N2 0.0278(14) 0.0302(15) 0.0366(15) -0.0024(12) 0.0063(12) 0.0003(12) N3 0.0410(18) 0.0322(17) 0.057(2) -0.0070(15) 0.0090(16) -0.0081(14) O1 0.0230(13) 0.0602(19) 0.072(2) -0.0163(16) 0.0040(13) -0.0053(13) O2 0.0429(15) 0.0314(14) 0.0711(19) 0.0034(13) 0.0068(14) 0.0100(12) O3 0.0328(14) 0.072(2) 0.0497(17) 0.0007(15) 0.0068(12) 0.0005(14) S1 0.0615(7) 0.0361(6) 0.0717(8) -0.0127(5) 0.0203(6) -0.0188(5) _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 1.287(4) . ? C1 N1 1.359(4) . ? C1 C2 1.434(5) . ? C2 C3 1.342(6) . ? C2 H2 0.9300 . ? C3 C4 1.415(6) . ? C3 H3 0.9300 . ? C4 C5 1.388(5) . ? C4 C11 1.422(5) . ? C5 N1 1.361(4) . ? C5 C6 1.429(5) . ? C6 N2 1.359(4) . ? C6 C10 1.406(5) . ? C7 N2 1.330(4) . ? C7 C8 1.393(5) . ? C7 H7 0.9300 . ? C8 C9 1.358(6) . ? C8 H8 0.9300 . ? C9 C10 1.410(5) . ? C9 H9 0.9300 . ? C10 C12 1.419(5) . ? C11 C12 1.350(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 N3 1.154(5) . ? C13 S1 1.627(4) . ? C14 O3 1.374(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O2 1.410(5) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? Cu1 N3 1.942(3) . ? Cu1 O2 1.968(3) . ? Cu1 N2 2.001(3) . ? Cu1 N1 2.008(3) . ? Cu1 O3 2.543(3) . ? O1 H1 0.8200 . ? O3 H4 0.8200 . ? 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 N1 120.4(3) . . ? O1 C1 C2 120.5(3) . . ? N1 C1 C2 119.1(3) . . ? C3 C2 C1 122.1(4) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C2 C3 C4 118.9(4) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 117.3(4) . . ? C5 C4 C11 119.1(4) . . ? C3 C4 C11 123.6(3) . . ? N1 C5 C4 124.4(3) . . ? N1 C5 C6 116.4(3) . . ? C4 C5 C6 119.2(3) . . ? N2 C6 C10 122.7(3) . . ? N2 C6 C5 116.6(3) . . ? C10 C6 C5 120.7(3) . . ? N2 C7 C8 121.6(4) . . ? N2 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C9 C8 C7 120.8(4) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 119.2(4) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C6 C10 C9 117.0(3) . . ? C6 C10 C12 118.5(3) . . ? C9 C10 C12 124.5(4) . . ? C12 C11 C4 122.0(4) . . ? C12 C11 H11 119.0 . . ? C4 C11 H11 119.0 . . ? C11 C12 C10 120.5(4) . . ? C11 C12 H12 119.7 . . ? C10 C12 H12 119.7 . . ? N3 C13 S1 179.3(4) . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 Cu1 O2 91.98(13) . . ? N3 Cu1 N2 95.07(13) . . ? O2 Cu1 N2 171.94(11) . . ? N3 Cu1 N1 175.68(13) . . ? O2 Cu1 N1 90.72(12) . . ? N2 Cu1 N1 82.47(12) . . ? N3 Cu1 O3 92.79(12) . . ? O2 Cu1 O3 91.62(11) . . ? N2 Cu1 O3 84.16(10) . . ? N1 Cu1 O3 90.50(10) . . ? C1 N1 C5 118.2(3) . . ? C1 N1 Cu1 129.7(2) . . ? C5 N1 Cu1 112.1(2) . . ? C7 N2 C6 118.7(3) . . ? C7 N2 Cu1 128.9(3) . . ? C6 N2 Cu1 112.3(2) . . ? C13 N3 Cu1 166.2(3) . . ? C1 O1 H1 109.5 . . ? C15 O2 Cu1 125.8(3) . . ? C14 O3 Cu1 127.6(3) . . ? C14 O3 H4 109.5 . . ? Cu1 O3 H4 105.4 . . ? 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 O1 C1 C2 C3 -179.5(4) . . . . ? N1 C1 C2 C3 -0.5(6) . . . . ? C1 C2 C3 C4 -0.7(6) . . . . ? C2 C3 C4 C5 0.4(6) . . . . ? C2 C3 C4 C11 -179.7(4) . . . . ? C3 C4 C5 N1 1.2(6) . . . . ? C11 C4 C5 N1 -178.7(3) . . . . ? C3 C4 C5 C6 -179.7(3) . . . . ? C11 C4 C5 C6 0.4(5) . . . . ? N1 C5 C6 N2 -1.6(5) . . . . ? C4 C5 C6 N2 179.2(3) . . . . ? N1 C5 C6 C10 179.0(3) . . . . ? C4 C5 C6 C10 -0.2(5) . . . . ? N2 C7 C8 C9 -1.0(6) . . . . ? C7 C8 C9 C10 0.3(6) . . . . ? N2 C6 C10 C9 -1.7(5) . . . . ? C5 C6 C10 C9 177.7(3) . . . . ? N2 C6 C10 C12 179.9(3) . . . . ? C5 C6 C10 C12 -0.8(5) . . . . ? C8 C9 C10 C6 0.9(6) . . . . ? C8 C9 C10 C12 179.2(4) . . . . ? C5 C4 C11 C12 0.4(6) . . . . ? C3 C4 C11 C12 -179.5(4) . . . . ? C4 C11 C12 C10 -1.4(7) . . . . ? C6 C10 C12 C11 1.6(6) . . . . ? C9 C10 C12 C11 -176.8(4) . . . . ? O1 C1 N1 C5 -179.0(3) . . . . ? C2 C1 N1 C5 2.0(5) . . . . ? O1 C1 N1 Cu1 0.2(5) . . . . ? C2 C1 N1 Cu1 -178.8(3) . . . . ? C4 C5 N1 C1 -2.4(5) . . . . ? C6 C5 N1 C1 178.4(3) . . . . ? C4 C5 N1 Cu1 178.2(3) . . . . ? C6 C5 N1 Cu1 -0.9(4) . . . . ? N3 Cu1 N1 C1 -121.6(16) . . . . ? O2 Cu1 N1 C1 7.2(3) . . . . ? N2 Cu1 N1 C1 -177.2(3) . . . . ? O3 Cu1 N1 C1 98.8(3) . . . . ? N3 Cu1 N1 C5 57.7(17) . . . . ? O2 Cu1 N1 C5 -173.5(2) . . . . ? N2 Cu1 N1 C5 2.1(2) . . . . ? O3 Cu1 N1 C5 -81.9(2) . . . . ? C8 C7 N2 C6 0.3(5) . . . . ? C8 C7 N2 Cu1 178.3(3) . . . . ? C10 C6 N2 C7 1.1(5) . . . . ? C5 C6 N2 C7 -178.3(3) . . . . ? C10 C6 N2 Cu1 -177.3(3) . . . . ? C5 C6 N2 Cu1 3.4(4) . . . . ? N3 Cu1 N2 C7 2.4(3) . . . . ? O2 Cu1 N2 C7 -148.6(8) . . . . ? N1 Cu1 N2 C7 178.9(3) . . . . ? O3 Cu1 N2 C7 -89.9(3) . . . . ? N3 Cu1 N2 C6 -179.4(2) . . . . ? O2 Cu1 N2 C6 29.6(10) . . . . ? N1 Cu1 N2 C6 -3.0(2) . . . . ? O3 Cu1 N2 C6 88.3(2) . . . . ? S1 C13 N3 Cu1 -31(36) . . . . ? O2 Cu1 N3 C13 -48.0(14) . . . . ? N2 Cu1 N3 C13 135.9(14) . . . . ? N1 Cu1 N3 C13 81(2) . . . . ? O3 Cu1 N3 C13 -139.7(14) . . . . ? N3 Cu1 O2 C15 41.8(4) . . . . ? N2 Cu1 O2 C15 -167.1(8) . . . . ? N1 Cu1 O2 C15 -134.8(4) . . . . ? O3 Cu1 O2 C15 134.7(4) . . . . ? N3 Cu1 O3 C14 80.6(3) . . . . ? O2 Cu1 O3 C14 -11.4(3) . . . . ? N2 Cu1 O3 C14 175.5(3) . . . . ? N1 Cu1 O3 C14 -102.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H4 O1 0.82 1.88 2.697(4) 171.6 1_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.988 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.098