# 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_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Natarajan, Karuppannan' _publ_contact_author_email 'k natraj6@yahoo.com' _publ_section_title ; Effect of terminal N-substitution in 2-oxo-1,2-dihydroquinoline-3-carbaldehyde thiosemicarbazones on the Mode of Coordination, Structure, Interaction with Protein, Radical Scavenging and Cytotoxic Activity of Copper(II) complexes ; loop_ _publ_author_name 'D.Senthil Raja' G.Paramaguru N.Bhuvanesh J.Reibenspies ; R.Renganathan ; K.Natarajan # Attachment '- 2.cif' data_twin5 _database_code_depnum_ccdc_archive 'CCDC 763001' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 Cl2 Cu N4 O2.50 S' _chemical_formula_weight 421.78 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 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 11.042(5) _cell_length_b 10.058(5) _cell_length_c 15.258(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.627(6) _cell_angle_gamma 90.00 _cell_volume 1615.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3626 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.827 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5673 _exptl_absorpt_correction_T_max 0.8384 _exptl_absorpt_process_details 'TWINABS; (Sheldrick, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'SMART CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8718 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8778 _reflns_number_gt 7162 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER-NONIUS, 2003)' _computing_cell_refinement ; SMART (BRUKER-NONIUS, 2003) ; _computing_data_reduction 'Bruker APEX-2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _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^)+(0.0719P)^2^+1.7300P] 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 8778 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.61176(3) 0.00118(3) 0.302273(19) 0.01738(10) Uani 1 1 d . . . Cl1 Cl 0.47891(6) -0.17422(6) 0.27014(4) 0.02309(14) Uani 1 1 d . . . Cl2 Cl 0.63676(6) 0.01619(5) 0.13259(4) 0.02228(14) Uani 1 1 d . . . S1 S 0.44955(6) 0.14092(6) 0.29819(4) 0.02183(14) Uani 1 1 d . . . C1 C 0.8469(2) 0.1637(2) 0.36085(16) 0.0183(5) Uani 1 1 d . . . H1 H 0.8863 0.2486 0.3677 0.022 Uiso 1 1 calc R . . C2 C 0.9276(2) 0.0475(2) 0.37513(15) 0.0164(5) Uani 1 1 d . . . C3 C 0.8765(2) -0.0865(2) 0.36963(15) 0.0171(5) Uani 1 1 d . . . C4 C 1.0932(2) -0.1714(2) 0.41440(15) 0.0193(5) Uani 1 1 d . . . C5 C 1.1429(2) -0.0413(2) 0.41960(16) 0.0192(5) Uani 1 1 d . . . C6 C 1.0559(2) 0.0661(2) 0.39953(16) 0.0199(5) Uani 1 1 d . . . H6 H 1.0880 0.1543 0.4032 0.024 Uiso 1 1 calc R . . C7 C 1.1740(2) -0.2818(3) 0.43195(16) 0.0241(5) Uani 1 1 d . . . H7 H 1.1404 -0.3692 0.4296 0.029 Uiso 1 1 calc R . . C8 C 1.3030(2) -0.2616(3) 0.45267(16) 0.0270(6) Uani 1 1 d . . . H8 H 1.3584 -0.3362 0.4637 0.032 Uiso 1 1 calc R . . C9 C 1.3540(2) -0.1333(3) 0.45779(17) 0.0275(6) Uani 1 1 d . . . H9 H 1.4432 -0.1218 0.4720 0.033 Uiso 1 1 calc R . . C10 C 1.2763(2) -0.0253(3) 0.44255(17) 0.0244(5) Uani 1 1 d . . . H10 H 1.3117 0.0615 0.4473 0.029 Uiso 1 1 calc R . . C11 C 0.5373(2) 0.2830(2) 0.32161(15) 0.0191(5) Uani 1 1 d . . . C12 C 0.3513(3) 0.4207(3) 0.3136(2) 0.0325(6) Uani 1 1 d . . . H12A H 0.3018 0.3696 0.2601 0.049 Uiso 1 1 calc R . . H12B H 0.3310 0.5154 0.3033 0.049 Uiso 1 1 calc R . . H12C H 0.3303 0.3908 0.3684 0.049 Uiso 1 1 calc R . . N1 N 0.72420(19) 0.15925(18) 0.33929(13) 0.0174(4) Uani 1 1 d . . . N2 N 0.66419(19) 0.28014(19) 0.33393(13) 0.0187(4) Uani 1 1 d . . . H2N H 0.7084 0.3613 0.3499 0.028 Uiso 1 1 d R . . N3 N 0.96251(19) -0.18623(19) 0.39072(13) 0.0183(4) Uani 1 1 d . . . H3N H 0.9380 -0.2604 0.3840 0.027 Uiso 1 1 d R . . N4 N 0.48684(19) 0.4004(2) 0.32718(14) 0.0230(5) Uani 1 1 d . . . H4N H 0.5292 0.4808 0.3440 0.035 Uiso 1 1 d R . . O1 O 0.76039(15) -0.11684(16) 0.34725(11) 0.0202(4) Uani 1 1 d . . . O20W O 0.8950(2) 0.12209(19) 0.07025(15) 0.0461(6) Uani 1 1 d . . . H20A H 0.9282 0.1916 0.1128 0.069 Uiso 1 1 d R . . H20B H 0.8222 0.1477 0.0134 0.069 Uiso 1 1 d R . . O21W O 0.3458(3) 0.8713(3) 0.0533(2) 0.0204(7) Uani 0.50 1 d P . . H21A H 0.3993 0.9311 0.0248 0.031 Uiso 0.50 1 d PR . . H21B H 0.3753 0.8818 0.1229 0.031 Uiso 0.50 1 d 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 Cu1 0.01850(17) 0.01387(16) 0.01951(16) -0.00047(11) 0.00535(12) -0.00116(10) Cl1 0.0229(3) 0.0192(3) 0.0272(3) -0.0025(2) 0.0076(2) -0.0049(2) Cl2 0.0302(3) 0.0144(3) 0.0228(3) 0.0005(2) 0.0089(3) 0.0023(2) S1 0.0232(3) 0.0194(3) 0.0229(3) -0.0004(2) 0.0069(2) -0.0003(2) C1 0.0253(13) 0.0118(11) 0.0186(11) 0.0002(9) 0.0078(10) -0.0016(9) C2 0.0211(12) 0.0138(11) 0.0145(10) 0.0011(9) 0.0055(9) -0.0008(9) C3 0.0221(12) 0.0152(11) 0.0148(10) -0.0014(9) 0.0067(9) 0.0012(9) C4 0.0227(12) 0.0202(12) 0.0144(11) -0.0015(9) 0.0050(9) 0.0010(9) C5 0.0204(12) 0.0231(12) 0.0151(11) 0.0012(9) 0.0068(9) 0.0009(10) C6 0.0252(13) 0.0168(12) 0.0178(11) 0.0007(9) 0.0067(10) -0.0022(10) C7 0.0291(14) 0.0248(13) 0.0165(11) -0.0013(10) 0.0042(10) 0.0066(11) C8 0.0263(13) 0.0372(15) 0.0159(11) -0.0020(11) 0.0039(10) 0.0089(11) C9 0.0197(13) 0.0452(17) 0.0182(12) -0.0016(11) 0.0065(10) 0.0047(11) C10 0.0225(13) 0.0309(14) 0.0209(12) 0.0004(10) 0.0083(10) -0.0039(11) C11 0.0254(12) 0.0197(12) 0.0130(10) 0.0025(9) 0.0070(9) 0.0019(10) C12 0.0317(15) 0.0316(15) 0.0354(15) -0.0024(12) 0.0119(12) 0.0103(12) N1 0.0234(11) 0.0133(9) 0.0151(9) 0.0007(7) 0.0051(8) 0.0026(8) N2 0.0246(11) 0.0101(9) 0.0220(10) -0.0004(8) 0.0079(9) 0.0007(8) N3 0.0231(11) 0.0117(9) 0.0195(10) -0.0012(8) 0.0057(8) -0.0011(8) N4 0.0230(11) 0.0188(11) 0.0273(11) -0.0013(9) 0.0076(9) 0.0037(8) O1 0.0199(9) 0.0134(8) 0.0256(9) 0.0008(7) 0.0047(7) -0.0017(7) O20W 0.0659(15) 0.0245(11) 0.0376(12) -0.0031(9) 0.0004(11) 0.0002(10) O21W 0.0251(18) 0.0192(17) 0.0157(15) 0.0016(13) 0.0043(14) -0.0015(14) _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 O1 1.9726(18) . ? Cu1 N1 1.991(2) . ? Cu1 Cl1 2.2515(10) . ? Cu1 S1 2.2628(10) . ? Cu1 Cl2 2.6897(14) . ? S1 C11 1.703(3) . ? C1 N1 1.294(3) . ? C1 C2 1.446(3) . ? C1 H1 0.9500 . ? C2 C6 1.364(3) . ? C2 C3 1.453(3) . ? C3 O1 1.261(3) . ? C3 N3 1.351(3) . ? C4 N3 1.385(3) . ? C4 C7 1.399(3) . ? C4 C5 1.411(3) . ? C5 C6 1.416(3) . ? C5 C10 1.417(4) . ? C6 H6 0.9500 . ? C7 C8 1.378(4) . ? C7 H7 0.9500 . ? C8 C9 1.401(4) . ? C8 H8 0.9500 . ? C9 C10 1.360(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 N4 1.319(3) . ? C11 N2 1.357(3) . ? C12 N4 1.462(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N1 N2 1.375(3) . ? N2 H2N 0.9440 . ? N3 H3N 0.7902 . ? N4 H4N 0.9310 . ? O20W H20A 0.9491 . ? O20W H20B 1.0211 . ? O21W H21A 1.0269 . ? O21W H21B 1.0168 . ? 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 Cu1 N1 90.01(8) . . ? O1 Cu1 Cl1 91.31(6) . . ? N1 Cu1 Cl1 175.39(6) . . ? O1 Cu1 S1 162.10(5) . . ? N1 Cu1 S1 86.11(7) . . ? Cl1 Cu1 S1 91.29(4) . . ? O1 Cu1 Cl2 92.96(5) . . ? N1 Cu1 Cl2 89.50(6) . . ? Cl1 Cu1 Cl2 94.84(3) . . ? S1 Cu1 Cl2 104.46(2) . . ? C11 S1 Cu1 96.91(9) . . ? N1 C1 C2 124.1(2) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C6 C2 C1 118.2(2) . . ? C6 C2 C3 119.8(2) . . ? C1 C2 C3 122.0(2) . . ? O1 C3 N3 117.9(2) . . ? O1 C3 C2 125.8(2) . . ? N3 C3 C2 116.2(2) . . ? N3 C4 C7 121.2(2) . . ? N3 C4 C5 118.1(2) . . ? C7 C4 C5 120.7(2) . . ? C4 C5 C6 117.9(2) . . ? C4 C5 C10 118.5(2) . . ? C6 C5 C10 123.5(2) . . ? C2 C6 C5 122.3(2) . . ? C2 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C8 C7 C4 118.8(3) . . ? C8 C7 H7 120.6 . . ? C4 C7 H7 120.6 . . ? C7 C8 C9 121.3(2) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C5 120.4(2) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? N4 C11 N2 116.7(2) . . ? N4 C11 S1 122.71(19) . . ? N2 C11 S1 120.63(18) . . ? 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 . . ? C1 N1 N2 115.66(19) . . ? C1 N1 Cu1 127.91(16) . . ? N2 N1 Cu1 116.19(15) . . ? C11 N2 N1 119.07(19) . . ? C11 N2 H2N 116.7 . . ? N1 N2 H2N 123.2 . . ? C3 N3 C4 125.7(2) . . ? C3 N3 H3N 118.8 . . ? C4 N3 H3N 115.2 . . ? C11 N4 C12 123.4(2) . . ? C11 N4 H4N 127.5 . . ? C12 N4 H4N 108.9 . . ? C3 O1 Cu1 128.29(15) . . ? H20A O20W H20B 115.9 . . ? H21A O21W H21B 109.8 . . ? 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 Cu1 S1 C11 81.92(18) . . . . ? N1 Cu1 S1 C11 4.02(9) . . . . ? Cl1 Cu1 S1 C11 -179.80(8) . . . . ? Cl2 Cu1 S1 C11 -84.46(8) . . . . ? N1 C1 C2 C6 -178.6(2) . . . . ? N1 C1 C2 C3 -2.4(4) . . . . ? C6 C2 C3 O1 -179.4(2) . . . . ? C1 C2 C3 O1 4.4(3) . . . . ? C6 C2 C3 N3 0.7(3) . . . . ? C1 C2 C3 N3 -175.5(2) . . . . ? N3 C4 C5 C6 -0.5(3) . . . . ? C7 C4 C5 C6 179.0(2) . . . . ? N3 C4 C5 C10 -179.2(2) . . . . ? C7 C4 C5 C10 0.3(3) . . . . ? C1 C2 C6 C5 176.7(2) . . . . ? C3 C2 C6 C5 0.3(3) . . . . ? C4 C5 C6 C2 -0.4(3) . . . . ? C10 C5 C6 C2 178.1(2) . . . . ? N3 C4 C7 C8 178.2(2) . . . . ? C5 C4 C7 C8 -1.3(3) . . . . ? C4 C7 C8 C9 1.0(4) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? C8 C9 C10 C5 -1.2(4) . . . . ? C4 C5 C10 C9 1.0(4) . . . . ? C6 C5 C10 C9 -177.6(2) . . . . ? Cu1 S1 C11 N4 179.71(19) . . . . ? Cu1 S1 C11 N2 0.92(19) . . . . ? C2 C1 N1 N2 176.3(2) . . . . ? C2 C1 N1 Cu1 -9.7(3) . . . . ? O1 Cu1 N1 C1 14.4(2) . . . . ? Cl1 Cu1 N1 C1 121.0(7) . . . . ? S1 Cu1 N1 C1 176.9(2) . . . . ? Cl2 Cu1 N1 C1 -78.6(2) . . . . ? O1 Cu1 N1 N2 -171.61(15) . . . . ? Cl1 Cu1 N1 N2 -65.0(8) . . . . ? S1 Cu1 N1 N2 -9.10(14) . . . . ? Cl2 Cu1 N1 N2 95.43(15) . . . . ? N4 C11 N2 N1 172.67(19) . . . . ? S1 C11 N2 N1 -8.5(3) . . . . ? C1 N1 N2 C11 -172.9(2) . . . . ? Cu1 N1 N2 C11 12.4(3) . . . . ? O1 C3 N3 C4 178.3(2) . . . . ? C2 C3 N3 C4 -1.8(3) . . . . ? C7 C4 N3 C3 -177.7(2) . . . . ? C5 C4 N3 C3 1.7(3) . . . . ? N2 C11 N4 C12 178.6(2) . . . . ? S1 C11 N4 C12 -0.2(3) . . . . ? N3 C3 O1 Cu1 -174.06(15) . . . . ? C2 C3 O1 Cu1 6.0(3) . . . . ? N1 Cu1 O1 C3 -12.6(2) . . . . ? Cl1 Cu1 O1 C3 171.84(19) . . . . ? S1 Cu1 O1 C3 -89.9(2) . . . . ? Cl2 Cu1 O1 C3 76.92(19) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.546 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.102 # start Validation Reply Form _vrf_REFLT03_twin5 ; PROBLEM: Reflection count > 15% excess reflns - sys abs data present? RESPONSE: The data was collected from a twinned crystal. The reflections from both the twin components were used for least squares refinemnet using HKLF5 file. ; _vrf_PLAT021_twin5 ; PROBLEM: Ratio Unique / Expected Reflections too High ... 2.41 RESPONSE: The data was collected from a twinned crystal. The reflections from both the twin components were used for least squares refinemnet using HKLF5 file. ; # Attachment '- 1.cif' data_cuq1 _database_code_depnum_ccdc_archive 'CCDC 763002' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13.80 Cl2 Cu N4 O2.90 S' _chemical_formula_weight 414.96 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' Cl Cl 0.3639 0.7018 '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_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 12.4870(5) _cell_length_b 10.0729(4) _cell_length_c 12.6494(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.1650(10) _cell_angle_gamma 90.00 _cell_volume 1560.93(11) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 6476 _cell_measurement_theta_min 4.55 _cell_measurement_theta_max 60.65 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.766 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 6.532 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5078 _exptl_absorpt_correction_T_max 0.6577 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER GADDS D8 Discover' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11666 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.55 _diffrn_reflns_theta_max 60.78 _reflns_number_total 2340 _reflns_number_gt 2169 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'FRAMBO (BRUKER-NONIUS, 2003)' _computing_cell_refinement ; CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003) ; _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _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^)+(0.0386P)^2^+1.5843P] 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 SHELXL _refine_ls_extinction_coef 0.00041(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2340 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0694 _refine_ls_wR_factor_gt 0.0683 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.15435(3) 0.48501(3) 0.34597(3) 0.01401(14) Uani 1 1 d . . . S1 S 0.12085(5) 0.61948(6) 0.47905(5) 0.01642(17) Uani 1 1 d . . . Cl1 Cl 0.37119(5) 0.50607(6) 0.36267(5) 0.01790(17) Uani 1 1 d . . . Cl2 Cl 0.16389(5) 0.30279(6) 0.45147(4) 0.01682(17) Uani 1 1 d . . . O1 O 0.13437(14) 0.37144(16) 0.21684(13) 0.0178(4) Uani 1 1 d . . . N1 N 0.13235(15) 0.64592(19) 0.25269(15) 0.0130(4) Uani 1 1 d . . . N2 N 0.12370(16) 0.76502(19) 0.30449(16) 0.0141(4) Uani 1 1 d . . . H2N H 0.1132 0.8383 0.2653 0.017 Uiso 1 1 d R . . N3 N 0.12995(16) 0.3073(2) 0.04663(16) 0.0150(4) Uani 1 1 d . . . H3N H 0.1370 0.2227 0.0726 0.018 Uiso 1 1 d R . . N4 N 0.09438(17) 0.8796(2) 0.45145(17) 0.0200(5) Uani 1 1 d . . . H4M H 0.0730 0.8782 0.5191 0.024 Uiso 1 1 d R . . H4N H 0.0598 0.9498 0.4076 0.024 Uiso 1 1 d R . . C1 C 0.13293(19) 0.6534(2) 0.15124(19) 0.0141(5) Uani 1 1 d . . . H1 H 0.1311 0.7391 0.1197 0.017 Uiso 1 1 calc R . . C2 C 0.13617(19) 0.5404(2) 0.08236(19) 0.0145(5) Uani 1 1 d . . . C3 C 0.13374(18) 0.4048(2) 0.12069(19) 0.0141(5) Uani 1 1 d . . . C4 C 0.13174(19) 0.3266(3) -0.06146(19) 0.0161(5) Uani 1 1 d . . . C5 C 0.13517(19) 0.4577(3) -0.0990(2) 0.0167(5) Uani 1 1 d . . . C6 C 0.13641(19) 0.5622(3) -0.02434(19) 0.0158(5) Uani 1 1 d . . . H6 H 0.1374 0.6512 -0.0492 0.019 Uiso 1 1 calc R . . C7 C 0.1312(2) 0.2191(3) -0.1312(2) 0.0201(6) Uani 1 1 d . . . H7 H 0.1282 0.1307 -0.1058 0.024 Uiso 1 1 calc R . . C8 C 0.1350(2) 0.2434(3) -0.2375(2) 0.0229(6) Uani 1 1 d . . . H8 H 0.1359 0.1706 -0.2850 0.028 Uiso 1 1 calc R . . C9 C 0.1375(2) 0.3727(3) -0.2772(2) 0.0236(6) Uani 1 1 d . . . H9 H 0.1393 0.3870 -0.3510 0.028 Uiso 1 1 calc R . . C10 C 0.1372(2) 0.4790(3) -0.2094(2) 0.0199(6) Uani 1 1 d . . . H10 H 0.1383 0.5669 -0.2364 0.024 Uiso 1 1 calc R . . C11 C 0.11159(19) 0.7637(2) 0.40735(19) 0.0155(5) Uani 1 1 d . . . O20W O 0.61022(17) 0.6272(2) 0.37575(17) 0.0301(5) Uani 0.90 1 d P . . H20 H 0.6754 0.6096 0.4275 0.045 Uiso 0.90 1 d PR . . H21 H 0.5466 0.5875 0.3940 0.045 Uiso 0.90 1 d PR . . O30W O 0.52368(15) 0.60822(17) 0.15438(14) 0.0246(4) Uani 1 1 d . . . H30 H 0.5654 0.6303 0.2239 0.037 Uiso 1 1 d R . . H31 H 0.4727 0.6801 0.1431 0.037 Uiso 1 1 d 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 0.0194(2) 0.0118(2) 0.0108(2) 0.00023(14) 0.00286(15) 0.00091(14) S1 0.0216(3) 0.0158(3) 0.0121(3) -0.0005(2) 0.0040(2) 0.0019(2) Cl1 0.0185(3) 0.0139(3) 0.0219(3) -0.0024(2) 0.0054(2) -0.0008(2) Cl2 0.0219(3) 0.0152(3) 0.0137(3) 0.0027(2) 0.0043(2) 0.0011(2) O1 0.0275(10) 0.0128(8) 0.0124(9) 0.0000(7) 0.0019(7) -0.0010(7) N1 0.0135(10) 0.0113(10) 0.0135(10) -0.0030(8) 0.0012(8) -0.0001(8) N2 0.0190(11) 0.0095(10) 0.0133(10) 0.0003(8) 0.0016(8) 0.0012(8) N3 0.0192(11) 0.0121(10) 0.0127(10) -0.0010(9) 0.0008(8) 0.0021(8) N4 0.0265(12) 0.0157(11) 0.0181(11) -0.0030(9) 0.0050(9) 0.0042(9) C1 0.0146(12) 0.0125(12) 0.0150(12) 0.0005(10) 0.0023(9) -0.0018(10) C2 0.0120(12) 0.0153(13) 0.0159(12) 0.0000(10) 0.0021(9) -0.0009(10) C3 0.0112(12) 0.0165(13) 0.0138(13) -0.0011(10) 0.0005(9) -0.0001(10) C4 0.0114(12) 0.0210(13) 0.0148(12) -0.0021(11) -0.0001(9) 0.0014(10) C5 0.0130(12) 0.0210(14) 0.0160(13) 0.0007(11) 0.0026(10) 0.0003(11) C6 0.0158(12) 0.0144(12) 0.0169(12) -0.0002(10) 0.0023(10) -0.0019(10) C7 0.0195(13) 0.0200(13) 0.0188(13) -0.0042(11) -0.0011(11) 0.0039(11) C8 0.0199(14) 0.0289(15) 0.0190(14) -0.0086(12) 0.0014(11) 0.0031(12) C9 0.0210(14) 0.0362(16) 0.0138(13) -0.0029(12) 0.0036(10) 0.0001(12) C10 0.0212(14) 0.0245(14) 0.0141(13) 0.0015(11) 0.0041(10) -0.0017(11) C11 0.0110(12) 0.0182(13) 0.0167(13) -0.0030(11) 0.0012(10) -0.0010(10) O20W 0.0282(12) 0.0310(12) 0.0296(12) -0.0014(10) 0.0019(9) -0.0051(9) O30W 0.0327(11) 0.0203(9) 0.0203(10) -0.0002(8) 0.0041(8) 0.0018(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 Cu1 O1 1.9701(16) . ? Cu1 N1 1.992(2) . ? Cu1 Cl2 2.2589(7) . ? Cu1 S1 2.2618(7) . ? Cu1 Cl1 2.6832(7) . ? S1 C11 1.704(3) . ? O1 C3 1.260(3) . ? N1 C1 1.287(3) . ? N1 N2 1.381(3) . ? N2 C11 1.339(3) . ? N2 H2N 0.8847 . ? N3 C3 1.352(3) . ? N3 C4 1.386(3) . ? N3 H3N 0.9109 . ? N4 C11 1.330(3) . ? N4 H4M 0.9450 . ? N4 H4N 0.9489 . ? C1 C2 1.439(4) . ? C1 H1 0.9500 . ? C2 C6 1.368(3) . ? C2 C3 1.451(3) . ? C4 C7 1.397(4) . ? C4 C5 1.407(4) . ? C5 C6 1.412(4) . ? C5 C10 1.418(4) . ? C6 H6 0.9500 . ? C7 C8 1.376(4) . ? C7 H7 0.9500 . ? C8 C9 1.398(4) . ? C8 H8 0.9500 . ? C9 C10 1.372(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? O20W H20 0.9570 . ? O20W H21 0.9569 . ? O30W H30 0.9570 . ? O30W H31 0.9571 . ? 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 Cu1 N1 90.03(7) . . ? O1 Cu1 Cl2 90.10(5) . . ? N1 Cu1 Cl2 175.13(6) . . ? O1 Cu1 S1 162.33(6) . . ? N1 Cu1 S1 85.96(6) . . ? Cl2 Cu1 S1 92.47(2) . . ? O1 Cu1 Cl1 94.30(5) . . ? N1 Cu1 Cl1 90.21(6) . . ? Cl2 Cu1 Cl1 94.63(2) . . ? S1 Cu1 Cl1 102.90(2) . . ? C11 S1 Cu1 96.75(8) . . ? C3 O1 Cu1 128.41(16) . . ? C1 N1 N2 116.0(2) . . ? C1 N1 Cu1 127.67(17) . . ? N2 N1 Cu1 116.11(14) . . ? C11 N2 N1 119.1(2) . . ? C11 N2 H2N 121.4 . . ? N1 N2 H2N 118.4 . . ? C3 N3 C4 125.2(2) . . ? C3 N3 H3N 116.2 . . ? C4 N3 H3N 117.9 . . ? C11 N4 H4M 117.6 . . ? C11 N4 H4N 120.1 . . ? H4M N4 H4N 111.4 . . ? N1 C1 C2 124.3(2) . . ? N1 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C6 C2 C1 118.4(2) . . ? C6 C2 C3 119.0(2) . . ? C1 C2 C3 122.5(2) . . ? O1 C3 N3 117.9(2) . . ? O1 C3 C2 125.2(2) . . ? N3 C3 C2 116.9(2) . . ? N3 C4 C7 121.0(2) . . ? N3 C4 C5 118.2(2) . . ? C7 C4 C5 120.8(2) . . ? C4 C5 C6 118.1(2) . . ? C4 C5 C10 118.8(2) . . ? C6 C5 C10 123.1(2) . . ? C2 C6 C5 122.5(2) . . ? C2 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? C8 C7 C4 118.8(2) . . ? C8 C7 H7 120.6 . . ? C4 C7 H7 120.6 . . ? C7 C8 C9 121.6(2) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C10 C9 C8 120.0(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C5 120.0(2) . . ? C9 C10 H10 120.0 . . ? C5 C10 H10 120.0 . . ? N4 C11 N2 117.2(2) . . ? N4 C11 S1 121.68(18) . . ? N2 C11 S1 121.14(19) . . ? H20 O20W H21 113.1 . . ? H30 O30W H31 101.0 . . ? 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 Cu1 S1 C11 -81.80(19) . . . . ? N1 Cu1 S1 C11 -4.52(10) . . . . ? Cl2 Cu1 S1 C11 -179.90(8) . . . . ? Cl1 Cu1 S1 C11 84.77(8) . . . . ? N1 Cu1 O1 C3 13.1(2) . . . . ? Cl2 Cu1 O1 C3 -171.79(19) . . . . ? S1 Cu1 O1 C3 89.7(3) . . . . ? Cl1 Cu1 O1 C3 -77.13(19) . . . . ? O1 Cu1 N1 C1 -13.7(2) . . . . ? Cl2 Cu1 N1 C1 -105.2(7) . . . . ? S1 Cu1 N1 C1 -176.4(2) . . . . ? Cl1 Cu1 N1 C1 80.64(19) . . . . ? O1 Cu1 N1 N2 171.69(15) . . . . ? Cl2 Cu1 N1 N2 80.2(7) . . . . ? S1 Cu1 N1 N2 8.91(14) . . . . ? Cl1 Cu1 N1 N2 -94.01(14) . . . . ? C1 N1 N2 C11 173.4(2) . . . . ? Cu1 N1 N2 C11 -11.4(3) . . . . ? N2 N1 C1 C2 -177.0(2) . . . . ? Cu1 N1 C1 C2 8.4(3) . . . . ? N1 C1 C2 C6 180.0(2) . . . . ? N1 C1 C2 C3 3.1(4) . . . . ? Cu1 O1 C3 N3 173.20(15) . . . . ? Cu1 O1 C3 C2 -7.1(3) . . . . ? C4 N3 C3 O1 -178.1(2) . . . . ? C4 N3 C3 C2 2.2(3) . . . . ? C6 C2 C3 O1 179.2(2) . . . . ? C1 C2 C3 O1 -3.9(4) . . . . ? C6 C2 C3 N3 -1.1(3) . . . . ? C1 C2 C3 N3 175.8(2) . . . . ? C3 N3 C4 C7 177.8(2) . . . . ? C3 N3 C4 C5 -1.6(3) . . . . ? N3 C4 C5 C6 -0.1(3) . . . . ? C7 C4 C5 C6 -179.5(2) . . . . ? N3 C4 C5 C10 179.9(2) . . . . ? C7 C4 C5 C10 0.5(4) . . . . ? C1 C2 C6 C5 -177.5(2) . . . . ? C3 C2 C6 C5 -0.5(3) . . . . ? C4 C5 C6 C2 1.1(4) . . . . ? C10 C5 C6 C2 -179.0(2) . . . . ? N3 C4 C7 C8 -178.9(2) . . . . ? C5 C4 C7 C8 0.5(4) . . . . ? C4 C7 C8 C9 -1.1(4) . . . . ? C7 C8 C9 C10 0.6(4) . . . . ? C8 C9 C10 C5 0.5(4) . . . . ? C4 C5 C10 C9 -1.0(4) . . . . ? C6 C5 C10 C9 179.0(2) . . . . ? N1 N2 C11 N4 -174.5(2) . . . . ? N1 N2 C11 S1 6.9(3) . . . . ? Cu1 S1 C11 N4 -178.28(19) . . . . ? Cu1 S1 C11 N2 0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 60.78 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.745 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.064 # end Validation Reply Form # Attachment '- 3.cif' data_knb _database_code_depnum_ccdc_archive 'CCDC 772056' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 Cl2 Cu N4 O2 S' _chemical_formula_weight 440.82 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 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 7.392(6) _cell_length_b 24.362(19) _cell_length_c 9.914(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.872(10) _cell_angle_gamma 90.00 _cell_volume 1740(2) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4552 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 28.12 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 1.697 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5725 _exptl_absorpt_correction_T_max 0.8762 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'SMART CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13196 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3980 _reflns_number_gt 3197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER-NONIUS, 2003)' _computing_cell_refinement ; SMART (BRUKER-NONIUS, 2003) ; _computing_data_reduction SAINTplus _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _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^)+(0.0363P)^2^+0.2371P] 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 3980 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0799 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.19911(4) 0.360124(10) 0.33652(3) 0.01416(9) Uani 1 1 d . . . S1 S 0.33592(8) 0.42488(2) 0.49022(6) 0.01618(13) Uani 1 1 d . . . Cl1 Cl 0.09314(9) 0.42182(2) 0.17247(6) 0.02162(15) Uani 1 1 d . . . Cl2 Cl 0.65363(7) 0.22486(2) 0.38054(6) 0.01750(14) Uani 1 1 d . . . C1 C 0.2618(3) 0.25326(9) 0.4849(2) 0.0147(5) Uani 1 1 d . . . H1A H 0.3205 0.2324 0.5635 0.018 Uiso 1 1 calc R . . C2 C 0.1475(3) 0.22425(9) 0.3697(2) 0.0145(5) Uani 1 1 d . . . C3 C 0.0418(3) 0.25262(9) 0.2489(2) 0.0147(5) Uani 1 1 d . . . C4 C -0.0594(3) 0.16434(9) 0.1461(2) 0.0141(4) Uani 1 1 d . . . C5 C 0.0372(3) 0.13640(9) 0.2650(2) 0.0155(5) Uani 1 1 d . . . C6 C 0.1382(3) 0.16811(9) 0.3772(2) 0.0164(5) Uani 1 1 d . . . H6A H 0.2008 0.1500 0.4593 0.020 Uiso 1 1 calc R . . C7 C -0.1544(3) 0.13517(9) 0.0295(3) 0.0186(5) Uani 1 1 d . . . H7A H -0.2202 0.1542 -0.0501 0.022 Uiso 1 1 calc R . . C8 C -0.1510(3) 0.07852(9) 0.0321(3) 0.0192(5) Uani 1 1 d . . . H8A H -0.2141 0.0586 -0.0468 0.023 Uiso 1 1 calc R . . C9 C -0.0550(3) 0.04986(9) 0.1500(3) 0.0195(5) Uani 1 1 d . . . H9A H -0.0532 0.0109 0.1500 0.023 Uiso 1 1 calc R . . C10 C 0.0358(3) 0.07830(9) 0.2646(2) 0.0174(5) Uani 1 1 d . . . H10A H 0.0983 0.0588 0.3445 0.021 Uiso 1 1 calc R . . C11 C 0.4264(3) 0.38123(9) 0.6226(2) 0.0145(5) Uani 1 1 d . . . C12 C 0.5527(3) 0.45664(9) 0.7809(2) 0.0171(5) Uani 1 1 d . . . H12A H 0.4320 0.4754 0.7724 0.021 Uiso 1 1 calc R . . H12B H 0.6196 0.4745 0.7167 0.021 Uiso 1 1 calc R . . C13 C 0.6654(3) 0.46162(10) 0.9278(2) 0.0229(5) Uani 1 1 d . . . H13A H 0.6856 0.5005 0.9519 0.034 Uiso 1 1 d R . . H13B H 0.7854 0.4434 0.9355 0.034 Uiso 1 1 d R . . H13C H 0.5981 0.4442 0.9912 0.034 Uiso 1 1 d R . . C15 C 0.5580(3) 0.36460(10) 0.1786(3) 0.0237(6) Uani 1 1 d . . . H15A H 0.6870 0.3548 0.2058 0.036 Uiso 1 1 d R . . H15B H 0.5518 0.4013 0.2127 0.036 Uiso 1 1 d R . . H15C H 0.5095 0.3641 0.0803 0.036 Uiso 1 1 d R . . N1 N 0.2895(2) 0.30559(7) 0.48811(18) 0.0127(4) Uani 1 1 d . . . N2 N 0.4034(3) 0.32626(7) 0.60705(19) 0.0163(4) Uani 1 1 d . . . H2N H 0.4635 0.3048 0.6766 0.020 Uiso 1 1 d R . . N3 N -0.0558(3) 0.22099(7) 0.14572(19) 0.0140(4) Uani 1 1 d . . . H3N H -0.1223 0.2378 0.0764 0.017 Uiso 1 1 d R . . N4 N 0.5216(3) 0.39832(7) 0.74420(19) 0.0166(4) Uani 1 1 d . . . H4N H 0.5767 0.3728 0.8054 0.020 Uiso 1 1 d R . . O1 O 0.0328(2) 0.30380(6) 0.23242(16) 0.0182(4) Uani 1 1 d . . . O2 O 0.4507(2) 0.32860(6) 0.24432(16) 0.0187(4) Uani 1 1 d . . . H2O H 0.5137 0.3018 0.2848 0.022 Uiso 1 1 d 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 0.01602(16) 0.01198(15) 0.01311(16) 0.00144(10) 0.00034(11) 0.00034(10) S1 0.0184(3) 0.0133(3) 0.0151(3) 0.0012(2) 0.0000(2) 0.0013(2) Cl1 0.0305(3) 0.0135(3) 0.0170(3) 0.0031(2) -0.0030(2) 0.0010(2) Cl2 0.0163(3) 0.0164(3) 0.0184(3) -0.0020(2) 0.0007(2) -0.0001(2) C1 0.0130(11) 0.0165(11) 0.0146(11) 0.0028(8) 0.0032(9) 0.0016(9) C2 0.0131(11) 0.0175(11) 0.0129(11) 0.0020(8) 0.0029(9) -0.0016(9) C3 0.0118(11) 0.0170(11) 0.0154(11) 0.0005(8) 0.0031(9) -0.0003(9) C4 0.0098(10) 0.0144(11) 0.0186(12) 0.0016(8) 0.0044(9) -0.0006(9) C5 0.0128(11) 0.0170(11) 0.0179(12) 0.0016(8) 0.0063(9) 0.0006(9) C6 0.0144(11) 0.0172(11) 0.0180(12) 0.0036(9) 0.0041(9) 0.0013(9) C7 0.0167(12) 0.0212(12) 0.0172(12) 0.0006(9) 0.0026(10) -0.0001(9) C8 0.0154(12) 0.0200(12) 0.0227(13) -0.0034(9) 0.0051(10) -0.0033(9) C9 0.0200(12) 0.0145(11) 0.0237(13) 0.0001(9) 0.0046(10) -0.0024(9) C10 0.0155(12) 0.0146(11) 0.0226(13) 0.0041(9) 0.0050(10) -0.0007(9) C11 0.0106(11) 0.0173(11) 0.0164(12) 0.0003(9) 0.0045(9) 0.0023(9) C12 0.0160(12) 0.0162(11) 0.0177(12) -0.0012(9) 0.0007(9) -0.0002(9) C13 0.0284(14) 0.0214(12) 0.0180(12) -0.0007(9) 0.0029(11) -0.0056(10) C15 0.0237(13) 0.0253(13) 0.0217(13) 0.0008(10) 0.0042(11) -0.0057(10) N1 0.0116(9) 0.0143(9) 0.0119(9) -0.0007(7) 0.0019(7) 0.0004(7) N2 0.0182(10) 0.0154(9) 0.0131(10) 0.0010(7) -0.0013(8) 0.0009(8) N3 0.0118(9) 0.0148(9) 0.0147(9) 0.0029(7) 0.0013(8) 0.0007(7) N4 0.0191(10) 0.0141(9) 0.0151(10) 0.0012(7) 0.0005(8) 0.0016(8) O1 0.0181(9) 0.0128(8) 0.0204(9) 0.0025(6) -0.0029(7) -0.0010(6) O2 0.0202(9) 0.0168(8) 0.0202(9) 0.0036(6) 0.0066(7) 0.0016(7) _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 O1 1.9732(18) . ? Cu1 N1 2.006(2) . ? Cu1 Cl1 2.2249(13) . ? Cu1 S1 2.2687(13) . ? Cu1 O2 2.375(2) . ? S1 C11 1.706(2) . ? C1 N1 1.290(3) . ? C1 C2 1.445(3) . ? C2 C6 1.372(3) . ? C2 C3 1.451(3) . ? C3 O1 1.257(3) . ? C3 N3 1.354(3) . ? C4 N3 1.380(3) . ? C4 C7 1.404(3) . ? C4 C5 1.410(3) . ? C5 C10 1.415(3) . ? C5 C6 1.422(3) . ? C7 C8 1.380(3) . ? C8 C9 1.410(3) . ? C9 C10 1.372(3) . ? C11 N4 1.320(3) . ? C11 N2 1.354(3) . ? C12 N4 1.472(3) . ? C12 C13 1.513(3) . ? C15 O2 1.433(3) . ? N1 N2 1.382(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N1 89.77(8) . . ? O1 Cu1 Cl1 90.61(7) . . ? N1 Cu1 Cl1 178.17(6) . . ? O1 Cu1 S1 165.33(5) . . ? N1 Cu1 S1 86.17(8) . . ? Cl1 Cu1 S1 93.03(6) . . ? O1 Cu1 O2 91.36(8) . . ? N1 Cu1 O2 85.15(8) . . ? Cl1 Cu1 O2 96.63(6) . . ? S1 Cu1 O2 102.31(6) . . ? C11 S1 Cu1 97.07(10) . . ? N1 C1 C2 124.4(2) . . ? C6 C2 C1 118.2(2) . . ? C6 C2 C3 119.7(2) . . ? C1 C2 C3 122.1(2) . . ? O1 C3 N3 117.5(2) . . ? O1 C3 C2 125.7(2) . . ? N3 C3 C2 116.8(2) . . ? N3 C4 C7 120.7(2) . . ? N3 C4 C5 118.6(2) . . ? C7 C4 C5 120.7(2) . . ? C4 C5 C10 118.6(2) . . ? C4 C5 C6 118.1(2) . . ? C10 C5 C6 123.2(2) . . ? C2 C6 C5 121.5(2) . . ? C8 C7 C4 119.1(2) . . ? C7 C8 C9 120.9(2) . . ? C10 C9 C8 120.0(2) . . ? C9 C10 C5 120.6(2) . . ? N4 C11 N2 116.35(19) . . ? N4 C11 S1 122.94(18) . . ? N2 C11 S1 120.72(17) . . ? N4 C12 C13 109.74(18) . . ? C1 N1 N2 116.37(18) . . ? C1 N1 Cu1 127.68(16) . . ? N2 N1 Cu1 115.84(14) . . ? C11 N2 N1 119.66(18) . . ? C3 N3 C4 125.05(19) . . ? C11 N4 C12 123.53(19) . . ? C3 O1 Cu1 127.79(15) . . ? C15 O2 Cu1 122.50(15) . . ? 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 Cu1 S1 C11 76.6(2) . . . . ? N1 Cu1 S1 C11 2.38(9) . . . . ? Cl1 Cu1 S1 C11 -179.27(8) . . . . ? O2 Cu1 S1 C11 -81.80(9) . . . . ? N1 C1 C2 C6 176.5(2) . . . . ? N1 C1 C2 C3 -4.3(4) . . . . ? C6 C2 C3 O1 176.9(2) . . . . ? C1 C2 C3 O1 -2.2(4) . . . . ? C6 C2 C3 N3 -2.8(3) . . . . ? C1 C2 C3 N3 178.1(2) . . . . ? N3 C4 C5 C10 -179.1(2) . . . . ? C7 C4 C5 C10 -0.3(3) . . . . ? N3 C4 C5 C6 -1.8(3) . . . . ? C7 C4 C5 C6 177.0(2) . . . . ? C1 C2 C6 C5 -176.4(2) . . . . ? C3 C2 C6 C5 4.4(3) . . . . ? C4 C5 C6 C2 -2.1(3) . . . . ? C10 C5 C6 C2 175.1(2) . . . . ? N3 C4 C7 C8 178.2(2) . . . . ? C5 C4 C7 C8 -0.5(4) . . . . ? C4 C7 C8 C9 0.5(4) . . . . ? C7 C8 C9 C10 0.4(4) . . . . ? C8 C9 C10 C5 -1.2(4) . . . . ? C4 C5 C10 C9 1.1(3) . . . . ? C6 C5 C10 C9 -176.0(2) . . . . ? Cu1 S1 C11 N4 -178.68(18) . . . . ? Cu1 S1 C11 N2 1.40(19) . . . . ? C2 C1 N1 N2 -179.92(19) . . . . ? C2 C1 N1 Cu1 -3.9(3) . . . . ? O1 Cu1 N1 C1 11.9(2) . . . . ? Cl1 Cu1 N1 C1 113.8(17) . . . . ? S1 Cu1 N1 C1 177.79(19) . . . . ? O2 Cu1 N1 C1 -79.5(2) . . . . ? O1 Cu1 N1 N2 -172.04(15) . . . . ? Cl1 Cu1 N1 N2 -70.2(18) . . . . ? S1 Cu1 N1 N2 -6.15(14) . . . . ? O2 Cu1 N1 N2 96.57(15) . . . . ? N4 C11 N2 N1 173.34(18) . . . . ? S1 C11 N2 N1 -6.7(3) . . . . ? C1 N1 N2 C11 -174.5(2) . . . . ? Cu1 N1 N2 C11 8.9(3) . . . . ? O1 C3 N3 C4 179.1(2) . . . . ? C2 C3 N3 C4 -1.2(3) . . . . ? C7 C4 N3 C3 -175.3(2) . . . . ? C5 C4 N3 C3 3.5(3) . . . . ? N2 C11 N4 C12 -177.2(2) . . . . ? S1 C11 N4 C12 2.9(3) . . . . ? C13 C12 N4 C11 179.6(2) . . . . ? N3 C3 O1 Cu1 -163.82(14) . . . . ? C2 C3 O1 Cu1 16.4(3) . . . . ? N1 Cu1 O1 C3 -18.11(19) . . . . ? Cl1 Cu1 O1 C3 163.69(19) . . . . ? S1 Cu1 O1 C3 -91.9(3) . . . . ? O2 Cu1 O1 C3 67.0(2) . . . . ? O1 Cu1 O2 C15 127.95(16) . . . . ? N1 Cu1 O2 C15 -142.40(17) . . . . ? Cl1 Cu1 O2 C15 37.18(16) . . . . ? S1 Cu1 O2 C15 -57.40(16) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.434 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.086 # Attachment '- 4.cif' data_knb0401 _database_code_depnum_ccdc_archive 'CCDC 772085' #TrackingRef '- 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 Cl Cu N4 O2 S' _chemical_formula_weight 452.41 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 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 8.447(3) _cell_length_b 16.895(6) _cell_length_c 13.235(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.997(4) _cell_angle_gamma 90.00 _cell_volume 1854.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 9880 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 28.84 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 1.456 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4753 _exptl_absorpt_correction_T_max 0.6373 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'SMART CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20435 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4190 _reflns_number_gt 3920 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER-NONIUS, 2003)' _computing_cell_refinement ; SMART (BRUKER-NONIUS, 2003) ; _computing_data_reduction SAINTplus _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _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^)+(0.0334P)^2^+0.7547P] 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 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0267 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0632 _refine_ls_wR_factor_gt 0.0619 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.23082(2) 0.573962(9) 0.242997(12) 0.01648(6) Uani 1 1 d . . . S1 S 0.10720(4) 0.537934(19) 0.37155(3) 0.01976(8) Uani 1 1 d . . . Cl1 Cl 0.21562(6) 0.45175(2) 0.17507(3) 0.03354(11) Uani 1 1 d . . . C1 C 0.29127(16) 0.74416(8) 0.26667(10) 0.0161(3) Uani 1 1 d . . . H1A H 0.2788 0.7927 0.3006 0.019 Uiso 1 1 calc R . . C2 C 0.37158(16) 0.74738(8) 0.17933(10) 0.0155(3) Uani 1 1 d . . . C3 C 0.39784(15) 0.67716(8) 0.12115(10) 0.0158(3) Uani 1 1 d . . . C4 C 0.52779(15) 0.75887(8) 0.01009(10) 0.0154(3) Uani 1 1 d . . . C5 C 0.50475(16) 0.82762(8) 0.06597(10) 0.0156(3) Uani 1 1 d . . . C6 C 0.42571(16) 0.81933(8) 0.15094(10) 0.0166(3) Uani 1 1 d . . . H6A H 0.4096 0.8651 0.1895 0.020 Uiso 1 1 calc R . . C7 C 0.60657(16) 0.76254(8) -0.07434(10) 0.0174(3) Uani 1 1 d . . . H7A H 0.6244 0.7159 -0.1106 0.021 Uiso 1 1 calc R . . C8 C 0.65754(16) 0.83526(9) -0.10352(10) 0.0189(3) Uani 1 1 d . . . H8A H 0.7086 0.8386 -0.1614 0.023 Uiso 1 1 calc R . . C9 C 0.63516(17) 0.90424(9) -0.04906(11) 0.0194(3) Uani 1 1 d . . . H9A H 0.6710 0.9537 -0.0703 0.023 Uiso 1 1 calc R . . C10 C 0.56140(16) 0.90065(8) 0.03522(11) 0.0183(3) Uani 1 1 d . . . H10A H 0.5487 0.9474 0.0727 0.022 Uiso 1 1 calc R . . C11 C 0.10913(16) 0.63265(8) 0.42498(10) 0.0153(2) Uani 1 1 d . . . C12 C -0.00584(16) 0.70506(8) 0.56169(10) 0.0154(3) Uani 1 1 d . . . C13 C 0.00089(16) 0.78293(8) 0.52671(10) 0.0177(3) Uani 1 1 d . . . H13A H 0.0451 0.7941 0.4674 0.021 Uiso 1 1 calc R . . C14 C -0.05828(17) 0.84391(8) 0.58026(11) 0.0189(3) Uani 1 1 d . . . H14A H -0.0542 0.8969 0.5570 0.023 Uiso 1 1 calc R . . C15 C -0.12339(16) 0.82806(8) 0.66757(11) 0.0190(3) Uani 1 1 d . . . H15A H -0.1641 0.8700 0.7031 0.023 Uiso 1 1 calc R . . C16 C -0.12821(16) 0.75053(8) 0.70214(10) 0.0182(3) Uani 1 1 d . . . H16A H -0.1722 0.7394 0.7615 0.022 Uiso 1 1 calc R . . C17 C -0.06898(16) 0.68945(8) 0.65019(10) 0.0171(3) Uani 1 1 d . . . H17A H -0.0712 0.6367 0.6747 0.021 Uiso 1 1 calc R . . N1 N 0.23491(13) 0.68100(7) 0.30257(8) 0.0149(2) Uani 1 1 d . . . N2 N 0.16965(14) 0.69581(7) 0.38961(8) 0.0157(2) Uani 1 1 d . . . N3 N 0.47175(13) 0.68745(7) 0.03993(9) 0.0161(2) Uani 1 1 d . . . H3N H 0.4743 0.6460 -0.0025 0.019 Uiso 1 1 d R . . N4 N 0.04252(14) 0.63793(7) 0.51152(9) 0.0169(2) Uani 1 1 d . . . H4N H 0.0164 0.5922 0.5393 0.020 Uiso 1 1 d R . . O1 O 0.35702(12) 0.60775(6) 0.14047(8) 0.0200(2) Uani 1 1 d . . . C20 C 0.6788(2) 0.48091(11) 0.12503(16) 0.0433(5) Uani 1 1 d . . . H20A H 0.6421 0.5283 0.0847 0.065 Uiso 1 1 d R . . H20B H 0.7706 0.4577 0.1002 0.065 Uiso 1 1 d R . . H20C H 0.7119 0.4953 0.1977 0.065 Uiso 1 1 d R . . O20 O 0.55100(15) 0.42480(6) 0.11409(9) 0.0293(3) Uani 1 1 d . . . H20 H 0.4744 0.4487 0.1347 0.044 Uiso 1 1 d 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 0.02209(10) 0.01289(10) 0.01624(10) -0.00068(6) 0.00813(7) -0.00042(6) S1 0.02938(19) 0.01314(16) 0.01966(17) 0.00012(12) 0.01203(14) 0.00002(13) Cl1 0.0574(3) 0.01661(17) 0.0348(2) -0.00743(14) 0.02966(19) -0.00912(16) C1 0.0161(6) 0.0163(6) 0.0160(6) -0.0018(5) 0.0035(5) -0.0001(5) C2 0.0152(6) 0.0167(6) 0.0146(6) -0.0005(5) 0.0026(5) 0.0008(5) C3 0.0143(6) 0.0170(6) 0.0162(6) -0.0005(5) 0.0029(5) -0.0002(5) C4 0.0129(6) 0.0174(6) 0.0151(6) 0.0012(5) 0.0009(5) 0.0001(5) C5 0.0147(6) 0.0176(6) 0.0144(6) 0.0005(5) 0.0022(5) 0.0002(5) C6 0.0168(6) 0.0165(6) 0.0165(6) -0.0010(5) 0.0034(5) 0.0010(5) C7 0.0170(6) 0.0192(6) 0.0164(6) -0.0016(5) 0.0039(5) 0.0008(5) C8 0.0172(6) 0.0233(7) 0.0169(6) 0.0017(5) 0.0051(5) 0.0008(5) C9 0.0192(7) 0.0179(6) 0.0218(7) 0.0036(5) 0.0056(5) -0.0015(5) C10 0.0189(6) 0.0159(6) 0.0204(7) 0.0001(5) 0.0049(5) 0.0005(5) C11 0.0155(6) 0.0156(6) 0.0146(6) 0.0000(5) 0.0025(5) 0.0023(5) C12 0.0143(6) 0.0165(6) 0.0154(6) -0.0025(5) 0.0028(5) -0.0003(5) C13 0.0190(6) 0.0186(6) 0.0159(6) 0.0008(5) 0.0044(5) -0.0008(5) C14 0.0205(7) 0.0156(6) 0.0203(6) 0.0006(5) 0.0032(5) -0.0002(5) C15 0.0170(6) 0.0196(7) 0.0204(7) -0.0037(5) 0.0040(5) 0.0021(5) C16 0.0186(6) 0.0212(7) 0.0158(6) -0.0018(5) 0.0059(5) -0.0015(5) C17 0.0173(6) 0.0169(6) 0.0175(6) 0.0004(5) 0.0042(5) -0.0012(5) N1 0.0152(5) 0.0165(5) 0.0134(5) -0.0010(4) 0.0035(4) 0.0009(4) N2 0.0170(5) 0.0173(5) 0.0136(5) -0.0016(4) 0.0049(4) -0.0002(4) N3 0.0179(5) 0.0150(5) 0.0158(5) -0.0013(4) 0.0046(4) 0.0000(4) N4 0.0219(6) 0.0133(5) 0.0171(5) 0.0001(4) 0.0080(4) -0.0003(4) O1 0.0264(5) 0.0146(5) 0.0216(5) -0.0013(4) 0.0115(4) -0.0016(4) C20 0.0474(11) 0.0280(9) 0.0508(11) -0.0006(8) 0.0000(9) -0.0112(8) O20 0.0387(7) 0.0209(6) 0.0302(6) -0.0070(4) 0.0117(5) -0.0047(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 Cu1 O1 1.9636(11) . ? Cu1 N1 1.9704(13) . ? Cu1 S1 2.2436(7) . ? Cu1 Cl1 2.2458(8) . ? S1 C11 1.7483(15) . ? C1 N1 1.2952(18) . ? C1 C2 1.4486(18) . ? C1 H1A 0.9500 . ? C2 C6 1.3760(19) . ? C2 C3 1.4542(18) . ? C3 O1 1.2622(17) . ? C3 N3 1.3533(17) . ? C4 N3 1.3812(18) . ? C4 C7 1.4067(19) . ? C4 C5 1.4104(19) . ? C5 C10 1.4110(19) . ? C5 C6 1.4200(19) . ? C6 H6A 0.9500 . ? C7 C8 1.381(2) . ? C7 H7A 0.9500 . ? C8 C9 1.402(2) . ? C8 H8A 0.9500 . ? C9 C10 1.379(2) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 N2 1.3078(18) . ? C11 N4 1.3719(18) . ? C12 C13 1.3994(19) . ? C12 C17 1.4015(19) . ? C12 N4 1.4134(17) . ? C13 C14 1.3961(19) . ? C13 H13A 0.9500 . ? C14 C15 1.397(2) . ? C14 H14A 0.9500 . ? C15 C16 1.391(2) . ? C15 H15A 0.9500 . ? C16 C17 1.3854(19) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? N1 N2 1.3913(16) . ? N3 H3N 0.9000 . ? N4 H4N 0.9001 . ? C20 O20 1.423(2) . ? C20 H20A 0.9799 . ? C20 H20B 0.9800 . ? C20 H20C 0.9801 . ? O20 H20 0.8500 . ? 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 Cu1 N1 92.25(5) . . ? O1 Cu1 S1 174.59(3) . . ? N1 Cu1 S1 85.45(4) . . ? O1 Cu1 Cl1 89.30(3) . . ? N1 Cu1 Cl1 177.73(3) . . ? S1 Cu1 Cl1 93.14(2) . . ? C11 S1 Cu1 95.08(5) . . ? N1 C1 C2 125.77(12) . . ? N1 C1 H1A 117.1 . . ? C2 C1 H1A 117.1 . . ? C6 C2 C1 118.79(12) . . ? C6 C2 C3 118.94(12) . . ? C1 C2 C3 122.27(12) . . ? O1 C3 N3 117.74(12) . . ? O1 C3 C2 125.14(12) . . ? N3 C3 C2 117.12(12) . . ? N3 C4 C7 120.36(12) . . ? N3 C4 C5 118.72(12) . . ? C7 C4 C5 120.92(12) . . ? C4 C5 C10 118.72(12) . . ? C4 C5 C6 117.83(12) . . ? C10 C5 C6 123.46(12) . . ? C2 C6 C5 122.30(12) . . ? C2 C6 H6A 118.8 . . ? C5 C6 H6A 118.8 . . ? C8 C7 C4 118.76(13) . . ? C8 C7 H7A 120.6 . . ? C4 C7 H7A 120.6 . . ? C7 C8 C9 121.07(13) . . ? C7 C8 H8A 119.5 . . ? C9 C8 H8A 119.5 . . ? C10 C9 C8 120.35(13) . . ? C10 C9 H9A 119.8 . . ? C8 C9 H9A 119.8 . . ? C9 C10 C5 120.15(13) . . ? C9 C10 H10A 119.9 . . ? C5 C10 H10A 119.9 . . ? N2 C11 N4 119.76(12) . . ? N2 C11 S1 125.18(10) . . ? N4 C11 S1 115.05(10) . . ? C13 C12 C17 119.96(12) . . ? C13 C12 N4 124.42(12) . . ? C17 C12 N4 115.58(12) . . ? C14 C13 C12 118.99(12) . . ? C14 C13 H13A 120.5 . . ? C12 C13 H13A 120.5 . . ? C13 C14 C15 120.93(13) . . ? C13 C14 H14A 119.5 . . ? C15 C14 H14A 119.5 . . ? C16 C15 C14 119.57(13) . . ? C16 C15 H15A 120.2 . . ? C14 C15 H15A 120.2 . . ? C17 C16 C15 120.15(13) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? C16 C17 C12 120.38(13) . . ? C16 C17 H17A 119.8 . . ? C12 C17 H17A 119.8 . . ? C1 N1 N2 112.76(11) . . ? C1 N1 Cu1 126.09(9) . . ? N2 N1 Cu1 121.13(8) . . ? C11 N2 N1 113.16(11) . . ? C3 N3 C4 125.07(12) . . ? C3 N3 H3N 117.8 . . ? C4 N3 H3N 116.7 . . ? C11 N4 C12 130.22(12) . . ? C11 N4 H4N 117.1 . . ? C12 N4 H4N 112.4 . . ? C3 O1 Cu1 127.98(9) . . ? O20 C20 H20A 109.5 . . ? O20 C20 H20B 109.4 . . ? H20A C20 H20B 109.5 . . ? O20 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C20 O20 H20 105.1 . . ? 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 O1 Cu1 S1 C11 65.3(3) . . . . ? N1 Cu1 S1 C11 0.24(5) . . . . ? Cl1 Cu1 S1 C11 -177.97(5) . . . . ? N1 C1 C2 C6 -179.61(13) . . . . ? N1 C1 C2 C3 0.0(2) . . . . ? C6 C2 C3 O1 178.56(13) . . . . ? C1 C2 C3 O1 -1.0(2) . . . . ? C6 C2 C3 N3 -1.52(18) . . . . ? C1 C2 C3 N3 178.90(12) . . . . ? N3 C4 C5 C10 -179.73(12) . . . . ? C7 C4 C5 C10 0.41(19) . . . . ? N3 C4 C5 C6 0.49(18) . . . . ? C7 C4 C5 C6 -179.37(12) . . . . ? C1 C2 C6 C5 -179.65(12) . . . . ? C3 C2 C6 C5 0.8(2) . . . . ? C4 C5 C6 C2 -0.2(2) . . . . ? C10 C5 C6 C2 179.99(13) . . . . ? N3 C4 C7 C8 178.46(12) . . . . ? C5 C4 C7 C8 -1.7(2) . . . . ? C4 C7 C8 C9 1.5(2) . . . . ? C7 C8 C9 C10 0.0(2) . . . . ? C8 C9 C10 C5 -1.3(2) . . . . ? C4 C5 C10 C9 1.1(2) . . . . ? C6 C5 C10 C9 -179.12(13) . . . . ? Cu1 S1 C11 N2 -0.23(12) . . . . ? Cu1 S1 C11 N4 -179.31(9) . . . . ? C17 C12 C13 C14 -1.0(2) . . . . ? N4 C12 C13 C14 176.71(13) . . . . ? C12 C13 C14 C15 0.0(2) . . . . ? C13 C14 C15 C16 0.5(2) . . . . ? C14 C15 C16 C17 -0.1(2) . . . . ? C15 C16 C17 C12 -0.9(2) . . . . ? C13 C12 C17 C16 1.4(2) . . . . ? N4 C12 C17 C16 -176.47(12) . . . . ? C2 C1 N1 N2 177.66(12) . . . . ? C2 C1 N1 Cu1 -4.2(2) . . . . ? O1 Cu1 N1 C1 6.56(12) . . . . ? S1 Cu1 N1 C1 -178.35(11) . . . . ? Cl1 Cu1 N1 C1 -126.5(8) . . . . ? O1 Cu1 N1 N2 -175.41(9) . . . . ? S1 Cu1 N1 N2 -0.32(9) . . . . ? Cl1 Cu1 N1 N2 51.5(9) . . . . ? N4 C11 N2 N1 179.07(11) . . . . ? S1 C11 N2 N1 0.03(17) . . . . ? C1 N1 N2 C11 178.53(11) . . . . ? Cu1 N1 N2 C11 0.26(15) . . . . ? O1 C3 N3 C4 -178.17(12) . . . . ? C2 C3 N3 C4 1.90(19) . . . . ? C7 C4 N3 C3 178.44(12) . . . . ? C5 C4 N3 C3 -1.41(19) . . . . ? N2 C11 N4 C12 15.3(2) . . . . ? S1 C11 N4 C12 -165.54(11) . . . . ? C13 C12 N4 C11 2.8(2) . . . . ? C17 C12 N4 C11 -179.43(13) . . . . ? N3 C3 O1 Cu1 -173.64(9) . . . . ? C2 C3 O1 Cu1 6.3(2) . . . . ? N1 Cu1 O1 C3 -7.73(12) . . . . ? S1 Cu1 O1 C3 -72.5(4) . . . . ? Cl1 Cu1 O1 C3 170.61(11) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.358 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.072