# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Lobana, Tarlok' _publ_contact_author_email tarlokslobana@yahoo.co.in _publ_section_title ; Metal mediated C-S rupture of heterocyclic thioamides: in situ generation of 2,2\^a^2^-thio-di-2-imidazoline, 1,1'-dimethyl-2,2'-di-imidazolylsulfide, SO42- and their variable coordination to CuII ; loop_ _publ_author_name T.Lobana R.Sultana G.Hundal R.Butcher # Attachment '- CIF plain text.txt' data_[Cu{?2-N,N-(N2C3H5)2S}(m-O,OSO2)(?1-OH2)]n _database_code_depnum_ccdc_archive 'CCDC 729409' #CCDC no. 729409 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H12 Cu N4 O5 S2' _chemical_formula_sum 'C6 H12 Cu N4 O5 S2' _chemical_formula_weight 347.86 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.561(5) _cell_length_b 7.851(5) _cell_length_c 15.768(5) _cell_angle_alpha 90.0 _cell_angle_beta 98.490(5) _cell_angle_gamma 90.0 _cell_volume 1170.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 45 _cell_measurement_theta_min 12 _cell_measurement_theta_max 20 _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.974 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 2.242 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.663 _exptl_absorpt_correction_T_max 0.809 _exptl_absorpt_process_details 'psi-scans, North et al., 1968' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4 diffractometer' _diffrn_measurement_method theta-2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2316 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2180 _reflns_number_gt 1720 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'SHELXTL-PC (Sheldrick, 1993)' _computing_structure_solution 'SIR-92 (Altamore et. al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP,Mercury(Farrugia,1997;Bruno et.al.,2002)' _computing_publication_material 'WINGX,(Farrugia, 1999)' _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^)+(0.0526P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2180 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _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 0.3455(4) 0.8800(8) 0.4933(3) 0.0461(12) Uani 1 1 d . . . C2 C 0.3340(4) 0.8811(6) 0.3949(2) 0.0366(9) Uani 1 1 d . . . C3 C 0.1258(3) 0.8080(5) 0.4382(2) 0.0261(7) Uani 1 1 d . . . C4 C -0.1002(3) 0.7049(5) 0.5175(2) 0.0288(8) Uani 1 1 d . . . C5 C -0.2578(4) 0.6180(6) 0.6020(3) 0.0391(10) Uani 1 1 d . . . C6 C -0.1207(4) 0.6757(7) 0.6550(2) 0.0411(10) Uani 1 1 d . . . N1 N 0.1914(3) 0.8182(5) 0.36935(19) 0.0398(9) Uani 1 1 d . . . N2 N 0.2006(3) 0.8416(4) 0.51176(17) 0.0271(6) Uani 1 1 d . . . N3 N -0.0338(3) 0.7460(4) 0.59226(16) 0.0272(6) Uani 1 1 d . . . N4 N -0.2216(3) 0.6220(6) 0.5161(2) 0.0493(11) Uani 1 1 d . . . O1W O 0.3309(3) 0.9722(4) 0.67016(16) 0.0315(6) Uani 1 1 d . . . O2 O 0.0717(3) 0.9282(4) 0.73190(17) 0.0451(7) Uani 1 1 d . . . O3 O 0.2501(2) 1.1057(3) 0.81099(15) 0.0328(6) Uani 1 1 d . . . O4 O 0.0075(2) 1.1984(3) 0.78464(16) 0.0351(6) Uani 1 1 d . . . O5 O 0.0747(3) 0.9686(4) 0.88223(15) 0.0404(7) Uani 1 1 d . . . S1 S -0.05229(9) 0.74743(14) 0.41682(5) 0.0363(2) Uani 1 1 d . . . S2 S 0.10137(8) 1.04947(12) 0.80381(5) 0.0260(2) Uani 1 1 d . . . Cu Cu 0.14880(4) 0.85362(6) 0.62790(2) 0.02354(14) Uani 1 1 d . . . H2W H 0.389(4) 0.895(6) 0.684(3) 0.035(12) Uiso 1 1 d . . . H1W H 0.314(4) 1.013(6) 0.708(3) 0.034(13) Uiso 1 1 d . . . H2A H 0.343(4) 0.990(7) 0.376(3) 0.053(14) Uiso 1 1 d . . . H5B H -0.340(5) 0.711(6) 0.601(3) 0.053(13) Uiso 1 1 d . . . H1 H 0.142(4) 0.813(5) 0.319(3) 0.038(11) Uiso 1 1 d . . . H5A H -0.288(4) 0.511(6) 0.619(2) 0.039(11) Uiso 1 1 d . . . H2B H 0.396(4) 0.805(6) 0.377(3) 0.040(12) Uiso 1 1 d . . . H4 H -0.283(5) 0.594(6) 0.470(3) 0.044(12) Uiso 1 1 d . . . H1B H 0.410(5) 0.792(6) 0.513(3) 0.056(14) Uiso 1 1 d . . . H1A H 0.378(6) 0.993(8) 0.514(3) 0.078(17) Uiso 1 1 d . . . H6A H -0.135(5) 0.754(6) 0.698(3) 0.050(13) Uiso 1 1 d . . . H6B H -0.069(5) 0.579(8) 0.685(3) 0.073(17) 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 0.0229(18) 0.089(4) 0.0267(19) 0.004(2) 0.0056(15) -0.016(2) C2 0.0290(19) 0.054(3) 0.0286(19) 0.0037(18) 0.0088(15) -0.0034(19) C3 0.0242(16) 0.0328(19) 0.0207(16) 0.0010(14) 0.0009(13) 0.0020(14) C4 0.0215(16) 0.039(2) 0.0250(16) -0.0046(15) 0.0015(13) -0.0024(15) C5 0.0300(19) 0.050(3) 0.039(2) -0.0055(19) 0.0099(16) -0.0131(18) C6 0.036(2) 0.063(3) 0.0254(18) -0.004(2) 0.0065(16) -0.022(2) N1 0.0296(16) 0.074(3) 0.0153(14) 0.0017(15) 0.0007(12) -0.0016(16) N2 0.0200(13) 0.0407(17) 0.0194(13) 0.0021(13) -0.0010(10) -0.0052(13) N3 0.0232(14) 0.0410(17) 0.0163(13) 0.0015(12) 0.0001(11) -0.0085(13) N4 0.0306(17) 0.090(3) 0.0260(16) -0.0140(18) 0.0007(13) -0.0269(19) O1W 0.0262(13) 0.0430(17) 0.0246(13) -0.0073(13) 0.0015(11) -0.0027(13) O2 0.0306(13) 0.068(2) 0.0376(14) -0.0283(15) 0.0095(11) -0.0196(14) O3 0.0192(11) 0.0449(15) 0.0326(13) -0.0167(11) -0.0022(10) -0.0034(11) O4 0.0221(12) 0.0468(16) 0.0346(13) 0.0069(12) -0.0018(10) 0.0031(11) O5 0.0336(13) 0.0599(18) 0.0264(12) 0.0097(13) 0.0002(10) 0.0040(13) S1 0.0240(4) 0.0650(7) 0.0182(4) 0.0002(4) -0.0032(3) -0.0071(4) S2 0.0192(4) 0.0409(5) 0.0168(4) -0.0028(4) -0.0009(3) -0.0011(4) Cu 0.0179(2) 0.0353(2) 0.0164(2) -0.00071(17) -0.00113(14) -0.00504(18) _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 N2 1.488(4) . ? C1 C2 1.539(5) . ? C1 H1B 0.95(5) . ? C1 H1A 0.98(6) . ? C2 N1 1.449(5) . ? C2 H2A 0.92(5) . ? C2 H2B 0.92(4) . ? C3 N2 1.297(4) . ? C3 N1 1.333(4) . ? C3 S1 1.752(3) . ? C4 N3 1.295(4) . ? C4 N4 1.328(5) . ? C4 S1 1.747(4) . ? C5 N4 1.447(5) . ? C5 C6 1.516(5) . ? C5 H5B 1.07(5) . ? C5 H5A 0.94(4) . ? C6 N3 1.489(4) . ? C6 H6A 0.94(5) . ? C6 H6B 0.98(6) . ? N1 H1 0.86(4) . ? N2 Cu 1.969(3) . ? N3 Cu 1.946(3) . ? N4 H4 0.90(4) . ? O1W Cu 2.000(3) . ? O1W H2W 0.83(5) . ? O1W H1W 0.72(4) . ? O2 S2 1.476(3) . ? O2 Cu 1.983(3) . ? O3 S2 1.477(2) . ? O3 Cu 2.319(3) 2_556 ? O4 S2 1.478(3) . ? O5 S2 1.446(3) . ? Cu O3 2.319(3) 2_546 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C2 105.6(3) . . ? N2 C1 H1B 112(3) . . ? C2 C1 H1B 107(3) . . ? N2 C1 H1A 112(3) . . ? C2 C1 H1A 108(3) . . ? H1B C1 H1A 113(4) . . ? N1 C2 C1 101.7(3) . . ? N1 C2 H2A 111(3) . . ? C1 C2 H2A 110(3) . . ? N1 C2 H2B 109(3) . . ? C1 C2 H2B 111(3) . . ? H2A C2 H2B 114(4) . . ? N2 C3 N1 116.9(3) . . ? N2 C3 S1 128.2(3) . . ? N1 C3 S1 114.9(2) . . ? N3 C4 N4 116.5(3) . . ? N3 C4 S1 128.4(3) . . ? N4 C4 S1 115.1(3) . . ? N4 C5 C6 101.7(3) . . ? N4 C5 H5B 104(2) . . ? C6 C5 H5B 112(2) . . ? N4 C5 H5A 114(2) . . ? C6 C5 H5A 113(2) . . ? H5B C5 H5A 111(3) . . ? N3 C6 C5 105.5(3) . . ? N3 C6 H6A 113(3) . . ? C5 C6 H6A 113(3) . . ? N3 C6 H6B 108(3) . . ? C5 C6 H6B 111(3) . . ? H6A C6 H6B 106(4) . . ? C3 N1 C2 109.3(3) . . ? C3 N1 H1 119(3) . . ? C2 N1 H1 130(3) . . ? C3 N2 C1 105.8(3) . . ? C3 N2 Cu 131.4(2) . . ? C1 N2 Cu 122.8(2) . . ? C4 N3 C6 105.4(3) . . ? C4 N3 Cu 132.0(2) . . ? C6 N3 Cu 122.3(2) . . ? C4 N4 C5 109.0(3) . . ? C4 N4 H4 127(3) . . ? C5 N4 H4 123(3) . . ? Cu O1W H2W 105(3) . . ? Cu O1W H1W 101(3) . . ? H2W O1W H1W 109(4) . . ? S2 O2 Cu 140.63(17) . . ? S2 O3 Cu 128.32(14) . 2_556 ? C4 S1 C3 104.76(15) . . ? O5 S2 O2 109.61(19) . . ? O5 S2 O3 110.80(15) . . ? O2 S2 O3 108.98(14) . . ? O5 S2 O4 110.10(16) . . ? O2 S2 O4 108.14(17) . . ? O3 S2 O4 109.15(16) . . ? N3 Cu N2 92.80(11) . . ? N3 Cu O2 86.54(11) . . ? N2 Cu O2 163.47(14) . . ? N3 Cu O1W 176.37(13) . . ? N2 Cu O1W 90.35(11) . . ? O2 Cu O1W 89.92(11) . . ? N3 Cu O3 93.26(11) . 2_546 ? N2 Cu O3 101.52(11) . 2_546 ? O2 Cu O3 95.00(12) . 2_546 ? O1W Cu O3 87.89(11) . 2_546 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C1 C2 N1 -8.4(5) . . . . ? N4 C5 C6 N3 13.4(5) . . . . ? N2 C3 N1 C2 -4.8(5) . . . . ? S1 C3 N1 C2 175.9(3) . . . . ? C1 C2 N1 C3 8.0(5) . . . . ? N1 C3 N2 C1 -1.1(5) . . . . ? S1 C3 N2 C1 178.1(3) . . . . ? N1 C3 N2 Cu 176.7(3) . . . . ? S1 C3 N2 Cu -4.1(5) . . . . ? C2 C1 N2 C3 6.1(5) . . . . ? C2 C1 N2 Cu -171.9(3) . . . . ? N4 C4 N3 C6 2.1(5) . . . . ? S1 C4 N3 C6 -179.2(3) . . . . ? N4 C4 N3 Cu 175.9(3) . . . . ? S1 C4 N3 Cu -5.4(6) . . . . ? C5 C6 N3 C4 -10.0(5) . . . . ? C5 C6 N3 Cu 175.4(3) . . . . ? N3 C4 N4 C5 7.3(5) . . . . ? S1 C4 N4 C5 -171.6(3) . . . . ? C6 C5 N4 C4 -12.6(5) . . . . ? N3 C4 S1 C3 15.0(4) . . . . ? N4 C4 S1 C3 -166.2(3) . . . . ? N2 C3 S1 C4 -10.3(4) . . . . ? N1 C3 S1 C4 168.9(3) . . . . ? Cu O2 S2 O5 -139.2(3) . . . . ? Cu O2 S2 O3 -17.8(4) . . . . ? Cu O2 S2 O4 100.8(3) . . . . ? Cu O3 S2 O5 -82.8(2) 2_556 . . . ? Cu O3 S2 O2 156.49(19) 2_556 . . . ? Cu O3 S2 O4 38.6(2) 2_556 . . . ? C4 N3 Cu N2 -7.9(4) . . . . ? C6 N3 Cu N2 165.1(3) . . . . ? C4 N3 Cu O2 155.6(4) . . . . ? C6 N3 Cu O2 -31.5(3) . . . . ? C4 N3 Cu O1W 142.1(18) . . . . ? C6 N3 Cu O1W -45(2) . . . . ? C4 N3 Cu O3 -109.6(4) . . . 2_546 ? C6 N3 Cu O3 63.3(3) . . . 2_546 ? C3 N2 Cu N3 12.7(4) . . . . ? C1 N2 Cu N3 -169.8(4) . . . . ? C3 N2 Cu O2 -74.6(5) . . . . ? C1 N2 Cu O2 102.9(5) . . . . ? C3 N2 Cu O1W -165.5(4) . . . . ? C1 N2 Cu O1W 12.0(4) . . . . ? C3 N2 Cu O3 106.6(3) . . . 2_546 ? C1 N2 Cu O3 -75.9(4) . . . 2_546 ? S2 O2 Cu N3 -164.8(3) . . . . ? S2 O2 Cu N2 -76.6(5) . . . . ? S2 O2 Cu O1W 14.4(3) . . . . ? S2 O2 Cu O3 102.2(3) . . . 2_546 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.471 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.103 #===End data_[CuII{?2-N,N-(N2C4H5)2S}(?2-O,OSO2)(?1-OH2)] _database_code_depnum_ccdc_archive 'CCDC 769468' #CCDC no. 769468 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 Cu N4 O5 S2' _chemical_formula_sum 'C8 H12 Cu N4 O5 S2' _chemical_formula_weight 371.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 'P 1 21/n 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.2777(2) _cell_length_b 16.8832(4) _cell_length_c 10.6197(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.377(2) _cell_angle_gamma 90.00 _cell_volume 1279.21(6) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5870 _cell_measurement_theta_min 5.2020 _cell_measurement_theta_max 32.5726 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.931 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 2.059 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.86374 _exptl_absorpt_correction_T_max 1.00000 _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) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8698 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.21 _diffrn_reflns_theta_max 32.65 _reflns_number_total 4243 _reflns_number_gt 3602 _reflns_threshold_expression I>2\s(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 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXLTL (Sheldrick, 2008)' _computing_publication_material SHELXLTL _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^)+(0.0429P)^2^+0.0617P] 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 4243 _refine_ls_number_parameters 189 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0721 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.45717(3) 0.549173(10) 0.753669(17) 0.00962(6) Uani 1 1 d . . . S1 S 0.23430(6) 0.45054(2) 0.44651(4) 0.01289(8) Uani 1 1 d . . . S2 S 0.75245(5) 0.61721(2) 0.88929(3) 0.01062(8) Uani 1 1 d . . . O1 O 0.58814(15) 0.65413(6) 0.79860(10) 0.0127(2) Uani 1 1 d . . . O2 O 0.68912(16) 0.53094(6) 0.88790(10) 0.0131(2) Uani 1 1 d . . . O3 O 0.92067(17) 0.62322(7) 0.83384(11) 0.0175(2) Uani 1 1 d . . . O4 O 0.77771(18) 0.65008(7) 1.01656(11) 0.0184(2) Uani 1 1 d . . . O1W O 0.27647(18) 0.56228(7) 0.89484(12) 0.0169(2) Uani 1 1 d D . . H1W1 H 0.165(2) 0.5740(13) 0.881(2) 0.025 Uiso 1 1 d D . . H1W2 H 0.292(3) 0.5337(12) 0.9548(19) 0.025 Uiso 1 1 d D . . N1 N 0.29215(18) 0.58794(8) 0.59834(12) 0.0109(2) Uani 1 1 d . . . N2 N 0.42460(19) 0.43748(8) 0.70249(13) 0.0115(2) Uani 1 1 d . . . N3 N 0.13476(19) 0.60096(8) 0.39875(12) 0.0119(2) Uani 1 1 d . . . N4 N 0.37510(19) 0.32669(8) 0.58934(12) 0.0131(2) Uani 1 1 d . . . C1 C 0.2447(2) 0.66690(9) 0.57580(15) 0.0137(3) Uani 1 1 d . . . H1A H 0.2750 0.7086 0.6364 0.016 Uiso 1 1 calc R . . C2 C 0.1478(2) 0.67518(9) 0.45309(15) 0.0137(3) Uani 1 1 d . . . H2A H 0.0986 0.7230 0.4128 0.016 Uiso 1 1 calc R . . C3 C 0.0413(2) 0.58096(11) 0.26763(15) 0.0168(3) Uani 1 1 d . . . H3A H -0.0553 0.5409 0.2703 0.025 Uiso 1 1 calc R . . H3B H 0.1335 0.5600 0.2204 0.025 Uiso 1 1 calc R . . H3C H -0.0170 0.6286 0.2244 0.025 Uiso 1 1 calc R . . C4 C 0.2238(2) 0.55042(8) 0.48921(14) 0.0105(3) Uani 1 1 d . . . C5 C 0.3518(2) 0.40613(9) 0.58865(14) 0.0110(3) Uani 1 1 d . . . C6 C 0.3146(2) 0.27153(10) 0.48282(15) 0.0162(3) Uani 1 1 d . . . H6A H 0.3156 0.2985 0.4013 0.024 Uiso 1 1 calc R . . H6B H 0.1875 0.2529 0.4842 0.024 Uiso 1 1 calc R . . H6C H 0.4004 0.2262 0.4917 0.024 Uiso 1 1 calc R . . C7 C 0.4669(2) 0.30600(9) 0.71154(15) 0.0146(3) Uani 1 1 d . . . H7A H 0.5029 0.2542 0.7416 0.017 Uiso 1 1 calc R . . C8 C 0.4954(2) 0.37415(9) 0.78006(15) 0.0133(3) Uani 1 1 d . . . H8A H 0.5549 0.3779 0.8679 0.016 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.01158(10) 0.00829(9) 0.00794(9) 0.00005(6) -0.00063(6) -0.00016(7) S1 0.01803(19) 0.01039(16) 0.00876(16) -0.00077(13) -0.00099(13) 0.00127(14) S2 0.01219(17) 0.00945(15) 0.00902(16) 0.00014(12) -0.00083(12) -0.00068(13) O1 0.0140(5) 0.0097(5) 0.0123(5) 0.0015(4) -0.0022(4) 0.0009(4) O2 0.0151(5) 0.0096(5) 0.0127(5) 0.0022(4) -0.0017(4) -0.0011(4) O3 0.0140(6) 0.0181(6) 0.0203(6) 0.0025(5) 0.0030(4) -0.0014(4) O4 0.0271(6) 0.0169(5) 0.0086(5) -0.0020(4) -0.0024(4) -0.0003(5) O1W 0.0158(6) 0.0222(6) 0.0134(5) 0.0054(5) 0.0048(4) 0.0038(5) N1 0.0128(6) 0.0096(5) 0.0093(6) -0.0007(5) -0.0005(4) 0.0007(5) N2 0.0144(6) 0.0100(6) 0.0096(6) 0.0014(4) 0.0008(4) -0.0002(5) N3 0.0128(6) 0.0123(6) 0.0095(5) 0.0015(5) -0.0002(4) 0.0010(5) N4 0.0160(6) 0.0105(6) 0.0122(6) -0.0013(5) 0.0015(5) 0.0001(5) C1 0.0159(7) 0.0101(6) 0.0140(7) -0.0002(6) 0.0000(5) 0.0009(6) C2 0.0151(7) 0.0102(6) 0.0149(7) 0.0014(6) 0.0005(5) 0.0012(6) C3 0.0175(8) 0.0207(8) 0.0104(7) 0.0004(6) -0.0016(5) 0.0024(6) C4 0.0111(7) 0.0105(6) 0.0094(6) 0.0012(5) 0.0007(5) 0.0002(5) C5 0.0116(7) 0.0108(6) 0.0106(6) 0.0003(5) 0.0023(5) 0.0001(5) C6 0.0204(8) 0.0126(7) 0.0142(7) -0.0046(6) 0.0005(6) 0.0001(6) C7 0.0180(7) 0.0129(7) 0.0118(7) 0.0021(6) 0.0002(5) 0.0013(6) C8 0.0161(7) 0.0118(7) 0.0114(6) 0.0022(5) 0.0008(5) 0.0006(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 1.9520(13) . ? Cu N2 1.9638(13) . ? Cu O2 2.0067(11) . ? Cu O1 2.0241(11) . ? Cu O1W 2.1918(12) . ? Cu S2 2.6059(4) . ? S1 C5 1.7500(15) . ? S1 C4 1.7518(15) . ? S2 O4 1.4389(12) . ? S2 O3 1.4629(12) . ? S2 O1 1.5138(11) . ? S2 O2 1.5269(11) . ? O1W H1W1 0.819(15) . ? O1W H1W2 0.789(15) . ? N1 C4 1.3283(19) . ? N1 C1 1.3860(19) . ? N2 C5 1.3303(19) . ? N2 C8 1.386(2) . ? N3 C4 1.3510(19) . ? N3 C2 1.375(2) . ? N3 C3 1.464(2) . ? N4 C5 1.3518(19) . ? N4 C7 1.3821(19) . ? N4 C6 1.464(2) . ? C1 C2 1.361(2) . ? C1 H1A 0.9500 . ? C2 H2A 0.9500 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.355(2) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? 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 Cu N2 93.87(5) . . ? N1 Cu O2 160.54(5) . . ? N2 Cu O2 95.05(5) . . ? N1 Cu O1 95.07(5) . . ? N2 Cu O1 158.66(5) . . ? O2 Cu O1 71.08(4) . . ? N1 Cu O1W 101.07(5) . . ? N2 Cu O1W 103.31(5) . . ? O2 Cu O1W 93.66(5) . . ? O1 Cu O1W 93.93(5) . . ? N1 Cu S2 128.47(4) . . ? N2 Cu S2 128.14(4) . . ? O2 Cu S2 35.77(3) . . ? O1 Cu S2 35.43(3) . . ? O1W Cu S2 96.78(4) . . ? C5 S1 C4 103.18(7) . . ? O4 S2 O3 112.91(7) . . ? O4 S2 O1 112.17(7) . . ? O3 S2 O1 109.52(7) . . ? O4 S2 O2 111.06(7) . . ? O3 S2 O2 109.71(7) . . ? O1 S2 O2 100.81(6) . . ? O4 S2 Cu 128.88(6) . . ? O3 S2 Cu 118.19(5) . . ? O1 S2 Cu 50.81(4) . . ? O2 S2 Cu 50.19(4) . . ? S2 O1 Cu 93.76(5) . . ? S2 O2 Cu 94.05(6) . . ? Cu O1W H1W1 127.3(15) . . ? Cu O1W H1W2 118.9(17) . . ? H1W1 O1W H1W2 106(2) . . ? C4 N1 C1 105.68(12) . . ? C4 N1 Cu 129.76(11) . . ? C1 N1 Cu 124.00(10) . . ? C5 N2 C8 105.54(13) . . ? C5 N2 Cu 129.66(11) . . ? C8 N2 Cu 124.47(11) . . ? C4 N3 C2 107.07(13) . . ? C4 N3 C3 126.77(13) . . ? C2 N3 C3 126.16(13) . . ? C5 N4 C7 107.03(13) . . ? C5 N4 C6 127.48(13) . . ? C7 N4 C6 125.49(13) . . ? C2 C1 N1 109.18(13) . . ? C2 C1 H1A 125.4 . . ? N1 C1 H1A 125.4 . . ? C1 C2 N3 106.73(13) . . ? C1 C2 H2A 126.6 . . ? N3 C2 H2A 126.6 . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 N3 111.33(13) . . ? N1 C4 S1 131.07(12) . . ? N3 C4 S1 117.60(11) . . ? N2 C5 N4 111.27(13) . . ? N2 C5 S1 130.74(12) . . ? N4 C5 S1 117.99(11) . . ? N4 C6 H6A 109.5 . . ? N4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 N4 106.50(14) . . ? C8 C7 H7A 126.8 . . ? N4 C7 H7A 126.8 . . ? C7 C8 N2 109.65(14) . . ? C7 C8 H8A 125.2 . . ? N2 C8 H8A 125.2 . . ? 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 Cu S2 O4 110.89(8) . . . . ? N2 Cu S2 O4 -111.93(8) . . . . ? O2 Cu S2 O4 -85.91(9) . . . . ? O1 Cu S2 O4 88.16(9) . . . . ? O1W Cu S2 O4 0.92(7) . . . . ? N1 Cu S2 O3 -70.26(8) . . . . ? N2 Cu S2 O3 66.92(8) . . . . ? O2 Cu S2 O3 92.94(8) . . . . ? O1 Cu S2 O3 -92.99(8) . . . . ? O1W Cu S2 O3 179.77(6) . . . . ? N1 Cu S2 O1 22.73(7) . . . . ? N2 Cu S2 O1 159.91(7) . . . . ? O2 Cu S2 O1 -174.07(8) . . . . ? O1W Cu S2 O1 -87.24(6) . . . . ? N1 Cu S2 O2 -163.20(7) . . . . ? N2 Cu S2 O2 -26.02(8) . . . . ? O1 Cu S2 O2 174.07(8) . . . . ? O1W Cu S2 O2 86.83(7) . . . . ? O4 S2 O1 Cu -122.85(6) . . . . ? O3 S2 O1 Cu 110.96(6) . . . . ? O2 S2 O1 Cu -4.63(6) . . . . ? N1 Cu O1 S2 -162.32(6) . . . . ? N2 Cu O1 S2 -47.92(15) . . . . ? O2 Cu O1 S2 3.66(5) . . . . ? O1W Cu O1 S2 96.18(6) . . . . ? O4 S2 O2 Cu 123.70(7) . . . . ? O3 S2 O2 Cu -110.78(6) . . . . ? O1 S2 O2 Cu 4.68(6) . . . . ? N1 Cu O2 S2 42.78(17) . . . . ? N2 Cu O2 S2 159.74(6) . . . . ? O1 Cu O2 S2 -3.63(5) . . . . ? O1W Cu O2 S2 -96.53(6) . . . . ? N2 Cu N1 C4 -13.28(14) . . . . ? O2 Cu N1 C4 103.87(19) . . . . ? O1 Cu N1 C4 147.32(14) . . . . ? O1W Cu N1 C4 -117.66(14) . . . . ? S2 Cu N1 C4 134.33(12) . . . . ? N2 Cu N1 C1 176.56(12) . . . . ? O2 Cu N1 C1 -66.3(2) . . . . ? O1 Cu N1 C1 -22.84(13) . . . . ? O1W Cu N1 C1 72.18(13) . . . . ? S2 Cu N1 C1 -35.83(14) . . . . ? N1 Cu N2 C5 13.76(14) . . . . ? O2 Cu N2 C5 -148.93(14) . . . . ? O1 Cu N2 C5 -100.85(18) . . . . ? O1W Cu N2 C5 116.10(14) . . . . ? S2 Cu N2 C5 -134.01(12) . . . . ? N1 Cu N2 C8 -173.73(13) . . . . ? O2 Cu N2 C8 23.59(13) . . . . ? O1 Cu N2 C8 71.67(19) . . . . ? O1W Cu N2 C8 -71.38(13) . . . . ? S2 Cu N2 C8 38.50(14) . . . . ? C4 N1 C1 C2 0.21(18) . . . . ? Cu N1 C1 C2 172.37(11) . . . . ? N1 C1 C2 N3 -0.03(18) . . . . ? C4 N3 C2 C1 -0.16(17) . . . . ? C3 N3 C2 C1 179.67(15) . . . . ? C1 N1 C4 N3 -0.32(17) . . . . ? Cu N1 C4 N3 -171.86(11) . . . . ? C1 N1 C4 S1 178.67(13) . . . . ? Cu N1 C4 S1 7.1(2) . . . . ? C2 N3 C4 N1 0.30(18) . . . . ? C3 N3 C4 N1 -179.52(14) . . . . ? C2 N3 C4 S1 -178.84(11) . . . . ? C3 N3 C4 S1 1.3(2) . . . . ? C5 S1 C4 N1 2.80(17) . . . . ? C5 S1 C4 N3 -178.26(12) . . . . ? C8 N2 C5 N4 -0.93(17) . . . . ? Cu N2 C5 N4 172.67(11) . . . . ? C8 N2 C5 S1 178.31(13) . . . . ? Cu N2 C5 S1 -8.1(2) . . . . ? C7 N4 C5 N2 0.60(18) . . . . ? C6 N4 C5 N2 -179.92(14) . . . . ? C7 N4 C5 S1 -178.74(11) . . . . ? C6 N4 C5 S1 0.7(2) . . . . ? C4 S1 C5 N2 -2.27(17) . . . . ? C4 S1 C5 N4 176.93(12) . . . . ? C5 N4 C7 C8 0.00(18) . . . . ? C6 N4 C7 C8 -179.49(15) . . . . ? N4 C7 C8 N2 -0.57(18) . . . . ? C5 N2 C8 C7 0.92(18) . . . . ? Cu N2 C8 C7 -173.10(11) . . . . ? 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 O1W H1W1 O3 0.819(15) 1.937(15) 2.7425(18) 167(2) 1_455 O1W H1W2 O2 0.789(15) 1.977(16) 2.7632(17) 174(2) 3_667 C2 H2A O1 0.95 2.40 3.3020(19) 159.2 4_575 C3 H3B O2 0.98 2.44 3.380(2) 161.7 3_666 C3 H3C O4 0.98 2.44 3.183(2) 132.7 1_454 C6 H6A O1 0.98 2.49 3.441(2) 162.4 3_666 C7 H7A O3 0.95 2.45 3.253(2) 141.8 2_646 _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.776 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.088 #===End data_[Cu2{?2-N,N-(N2C4H5)2S}2(\m-Cl)2Cl2] _database_code_depnum_ccdc_archive 'CCDC 769469' #CCDC no. 769469 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 Cl4 Cu2 N8 S2' _chemical_formula_sum 'C16 H20 Cl4 Cu2 N8 S2' _chemical_formula_weight 657.44 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '- P 2yn' 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 9.0530(10) _cell_length_b 8.4020(10) _cell_length_c 15.754(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.280(10) _cell_angle_gamma 90.00 _cell_volume 1195.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.827 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 2.425 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.6062 _exptl_absorpt_correction_T_max 0.7684 _exptl_absorpt_process_details 'PSISCANS, North e al., 1968' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Siemens P4 diffractometer' _diffrn_measurement_method \t-2\t _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 2365 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2219 _reflns_number_gt 1859 _reflns_threshold_expression >2sigma(I) _computing_data_collection XSCANS _computing_cell_refinement XSCANS _computing_data_reduction 'SHELXTL-PC (Sheldrick, 1993)' _computing_structure_solution 'SIR-92 (Altamore et. al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP,Mercury(Farrugia,1997;Bruno et.al.,2002)' _computing_publication_material 'WINGX,(Farrugia, 1999)' _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^)+(0.0588P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2219 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 Cl1 Cl 0.07924(9) -0.17039(9) 0.46336(5) 0.0327(2) Uani 1 1 d . . . Cl2 Cl 0.20163(10) 0.14201(11) 0.36097(5) 0.0372(2) Uani 1 1 d . . . C1 C 0.4014(4) 0.0172(4) 0.6528(2) 0.0265(7) Uani 1 1 d . . . C2 C 0.2031(4) -0.1189(4) 0.6672(2) 0.0348(8) Uani 1 1 d . . . H2 H 0.1095 -0.1634 0.6568 0.042 Uiso 1 1 calc R . . C3 C 0.2943(4) -0.1421(4) 0.7380(2) 0.0370(8) Uani 1 1 d . . . H3 H 0.2756 -0.2059 0.7842 0.044 Uiso 1 1 calc R . . C4 C 0.5452(4) -0.0395(5) 0.7924(2) 0.0437(9) Uani 1 1 d . . . H4A H 0.5281 -0.1047 0.8407 0.066 Uiso 1 1 calc R . . H4B H 0.5560 0.0695 0.8101 0.066 Uiso 1 1 calc R . . H4C H 0.6339 -0.0740 0.7681 0.066 Uiso 1 1 calc R . . C5 C 0.4075(4) 0.2983(4) 0.58182(19) 0.0263(7) Uani 1 1 d . . . C6 C 0.2220(4) 0.4265(4) 0.5222(2) 0.0331(8) Uani 1 1 d . . . H6 H 0.1328 0.4487 0.4913 0.040 Uiso 1 1 calc R . . C7 C 0.3122(4) 0.5345(4) 0.5603(2) 0.0353(8) Uani 1 1 d . . . H7 H 0.2975 0.6440 0.5608 0.042 Uiso 1 1 calc R . . C8 C 0.5513(5) 0.5234(5) 0.6538(3) 0.0482(10) Uani 1 1 d . . . H8A H 0.5406 0.6370 0.6541 0.072 Uiso 1 1 calc R . . H8B H 0.6447 0.4959 0.6327 0.072 Uiso 1 1 calc R . . H8C H 0.5475 0.4833 0.7106 0.072 Uiso 1 1 calc R . . N1 N 0.2712(3) -0.0191(3) 0.61306(17) 0.0284(6) Uani 1 1 d . . . N2 N 0.4196(3) -0.0536(3) 0.72888(17) 0.0297(6) Uani 1 1 d . . . N3 N 0.2815(3) 0.2767(3) 0.53562(17) 0.0275(6) Uani 1 1 d . . . N4 N 0.4312(3) 0.4531(3) 0.59890(18) 0.0308(6) Uani 1 1 d . . . S1 S 0.53341(9) 0.14670(10) 0.61386(6) 0.0329(2) Uani 1 1 d . . . Cu Cu 0.19231(4) 0.06733(5) 0.49844(2) 0.02597(15) 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 Cl1 0.0326(4) 0.0241(4) 0.0407(4) -0.0074(3) -0.0013(3) -0.0028(3) Cl2 0.0435(5) 0.0400(5) 0.0277(4) 0.0022(3) 0.0006(4) -0.0054(4) C1 0.0267(16) 0.0261(16) 0.0260(16) 0.0005(13) -0.0028(13) 0.0004(13) C2 0.0339(18) 0.0342(19) 0.0365(18) 0.0005(15) 0.0042(15) -0.0097(15) C3 0.043(2) 0.0375(19) 0.0316(18) 0.0057(15) 0.0096(16) -0.0068(17) C4 0.040(2) 0.056(2) 0.0334(19) 0.0070(18) -0.0097(16) -0.0049(19) C5 0.0263(16) 0.0258(16) 0.0266(16) 0.0003(13) 0.0010(13) -0.0033(14) C6 0.0327(18) 0.0292(18) 0.0364(18) 0.0047(14) -0.0033(15) 0.0068(15) C7 0.047(2) 0.0218(17) 0.0374(19) 0.0021(14) 0.0030(17) 0.0025(16) C8 0.049(2) 0.043(2) 0.051(2) -0.0042(18) -0.0053(19) -0.021(2) N1 0.0301(14) 0.0268(14) 0.0276(14) 0.0027(11) -0.0027(12) -0.0036(12) N2 0.0295(14) 0.0367(16) 0.0227(13) 0.0043(12) -0.0001(11) 0.0002(13) N3 0.0292(14) 0.0242(13) 0.0281(13) 0.0024(11) -0.0055(11) 0.0027(12) N4 0.0342(15) 0.0268(15) 0.0313(14) -0.0005(12) 0.0010(12) -0.0070(13) S1 0.0235(4) 0.0321(5) 0.0428(5) 0.0092(4) 0.0000(4) -0.0003(4) Cu 0.0283(2) 0.0223(2) 0.0265(2) -0.00051(15) -0.00364(16) -0.00244(16) _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 Cl1 Cu 2.2931(9) . ? Cl1 Cu 2.7159(10) 3_556 ? Cl2 Cu 2.2624(10) . ? C1 N1 1.328(4) . ? C1 N2 1.338(4) . ? C1 S1 1.760(3) . ? C2 C3 1.350(5) . ? C2 N1 1.375(4) . ? C2 H2 0.9300 . ? C3 N2 1.373(5) . ? C3 H3 0.9300 . ? C4 N2 1.462(4) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 N3 1.319(4) . ? C5 N4 1.343(4) . ? C5 S1 1.758(3) . ? C6 C7 1.333(5) . ? C6 N3 1.379(4) . ? C6 H6 0.9300 . ? C7 N4 1.378(5) . ? C7 H7 0.9300 . ? C8 N4 1.462(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N1 Cu 2.026(3) . ? N3 Cu 2.005(3) . ? Cu Cl1 2.7159(10) 3_556 ? 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 Cu Cl1 Cu 93.67(3) . 3_556 ? N1 C1 N2 111.4(3) . . ? N1 C1 S1 125.4(2) . . ? N2 C1 S1 123.1(2) . . ? C3 C2 N1 109.0(3) . . ? C3 C2 H2 125.5 . . ? N1 C2 H2 125.5 . . ? C2 C3 N2 107.2(3) . . ? C2 C3 H3 126.4 . . ? N2 C3 H3 126.4 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 N4 111.3(3) . . ? N3 C5 S1 125.1(3) . . ? N4 C5 S1 123.6(2) . . ? C7 C6 N3 109.4(3) . . ? C7 C6 H6 125.3 . . ? N3 C6 H6 125.3 . . ? C6 C7 N4 107.1(3) . . ? C6 C7 H7 126.5 . . ? N4 C7 H7 126.5 . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 N1 C2 105.7(3) . . ? C1 N1 Cu 125.4(2) . . ? C2 N1 Cu 128.9(2) . . ? C1 N2 C3 106.7(3) . . ? C1 N2 C4 127.9(3) . . ? C3 N2 C4 125.4(3) . . ? C5 N3 C6 105.7(3) . . ? C5 N3 Cu 126.5(2) . . ? C6 N3 Cu 127.7(2) . . ? C5 N4 C7 106.5(3) . . ? C5 N4 C8 127.6(3) . . ? C7 N4 C8 125.7(3) . . ? C5 S1 C1 96.03(15) . . ? N3 Cu N1 86.94(11) . . ? N3 Cu Cl2 89.62(8) . . ? N1 Cu Cl2 156.45(9) . . ? N3 Cu Cl1 175.99(8) . . ? N1 Cu Cl1 91.38(8) . . ? Cl2 Cu Cl1 93.37(3) . . ? N3 Cu Cl1 90.40(8) . 3_556 ? N1 Cu Cl1 100.45(8) . 3_556 ? Cl2 Cu Cl1 102.87(3) . 3_556 ? Cl1 Cu Cl1 86.33(3) . 3_556 ? 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 C2 C3 N2 1.1(4) . . . . ? N3 C6 C7 N4 0.0(4) . . . . ? N2 C1 N1 C2 -0.1(4) . . . . ? S1 C1 N1 C2 -178.1(3) . . . . ? N2 C1 N1 Cu 177.5(2) . . . . ? S1 C1 N1 Cu -0.5(4) . . . . ? C3 C2 N1 C1 -0.6(4) . . . . ? C3 C2 N1 Cu -178.1(2) . . . . ? N1 C1 N2 C3 0.7(4) . . . . ? S1 C1 N2 C3 178.8(3) . . . . ? N1 C1 N2 C4 -177.9(3) . . . . ? S1 C1 N2 C4 0.2(5) . . . . ? C2 C3 N2 C1 -1.1(4) . . . . ? C2 C3 N2 C4 177.6(4) . . . . ? N4 C5 N3 C6 0.3(4) . . . . ? S1 C5 N3 C6 -177.2(2) . . . . ? N4 C5 N3 Cu -176.9(2) . . . . ? S1 C5 N3 Cu 5.6(4) . . . . ? C7 C6 N3 C5 -0.2(4) . . . . ? C7 C6 N3 Cu 177.0(2) . . . . ? N3 C5 N4 C7 -0.3(4) . . . . ? S1 C5 N4 C7 177.2(2) . . . . ? N3 C5 N4 C8 174.5(3) . . . . ? S1 C5 N4 C8 -8.0(5) . . . . ? C6 C7 N4 C5 0.2(4) . . . . ? C6 C7 N4 C8 -174.7(3) . . . . ? N3 C5 S1 C1 -48.9(3) . . . . ? N4 C5 S1 C1 133.9(3) . . . . ? N1 C1 S1 C5 45.9(3) . . . . ? N2 C1 S1 C5 -131.9(3) . . . . ? C5 N3 Cu N1 36.7(3) . . . . ? C6 N3 Cu N1 -139.9(3) . . . . ? C5 N3 Cu Cl2 -120.0(3) . . . . ? C6 N3 Cu Cl2 63.4(3) . . . . ? C5 N3 Cu Cl1 101.9(11) . . . . ? C6 N3 Cu Cl1 -74.7(12) . . . . ? C5 N3 Cu Cl1 137.2(3) . . . 3_556 ? C6 N3 Cu Cl1 -39.5(3) . . . 3_556 ? C1 N1 Cu N3 -39.1(3) . . . . ? C2 N1 Cu N3 137.9(3) . . . . ? C1 N1 Cu Cl2 42.9(4) . . . . ? C2 N1 Cu Cl2 -140.1(3) . . . . ? C1 N1 Cu Cl1 144.6(3) . . . . ? C2 N1 Cu Cl1 -38.4(3) . . . . ? C1 N1 Cu Cl1 -128.9(3) . . . 3_556 ? C2 N1 Cu Cl1 48.1(3) . . . 3_556 ? Cu Cl1 Cu N3 35.3(11) 3_556 . . . ? Cu Cl1 Cu N1 100.38(8) 3_556 . . . ? Cu Cl1 Cu Cl2 -102.70(4) 3_556 . . . ? Cu Cl1 Cu Cl1 0.0 3_556 . . 3_556 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.467 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.089 #===End