# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email biplab@iitg.ernet.in _publ_contact_author_name 'Biplab Mondal' loop_ _publ_author_name 'Biplab Mondal' 'Moushumi Sarma' # Attachment '- cif L1.cif' data_L1 _database_code_depnum_ccdc_archive 'CCDC 829126' #TrackingRef '- cif L1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H10 N4 O2' _chemical_formula_weight 146.16 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 5.7944(6) _cell_length_b 10.0079(6) _cell_length_c 13.3326(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.710(6) _cell_angle_gamma 90.00 _cell_volume 766.16(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1185 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3343 _diffrn_reflns_av_R_equivalents 0.0698 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.43 _reflns_number_total 879 _reflns_number_gt 482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1179P)^2^+0.0713P] 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 879 _refine_ls_number_parameters 47 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.2463 _refine_ls_wR_factor_gt 0.2180 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _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 N1 N -0.0177(3) 0.54460(17) 0.14019(15) 0.0786(8) Uani 1 1 d . . . N2 N 0.1353(5) 0.6434(3) 0.1478(2) 0.1115(10) Uani 1 1 d . . . C1 C 0.0518(4) 0.4284(2) 0.2008(2) 0.0869(9) Uani 1 1 d . . . H1A H 0.2203 0.4262 0.2156 0.104 Uiso 1 1 calc R . . H1B H 0.0021 0.3485 0.1627 0.104 Uiso 1 1 calc R . . O1 O 0.0595(6) 0.7442(3) 0.1036(2) 0.1624(14) Uani 1 1 d . . . C2 C -0.2494(5) 0.5593(3) 0.0865(2) 0.1008(10) Uani 1 1 d . . . H2A H -0.3430 0.6099 0.1270 0.151 Uiso 1 1 calc R . . H2B H -0.3176 0.4726 0.0730 0.151 Uiso 1 1 calc R . . H2C H -0.2420 0.6051 0.0238 0.151 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 N1 0.0807(14) 0.0688(12) 0.0868(14) -0.0095(9) 0.0135(10) -0.0128(9) N2 0.127(2) 0.0972(17) 0.112(2) 0.0130(14) 0.0219(17) -0.0291(15) C1 0.0833(17) 0.0620(13) 0.114(2) -0.0129(12) 0.0094(14) 0.0077(11) O1 0.186(3) 0.125(2) 0.164(2) 0.0421(19) -0.022(2) -0.066(2) C2 0.098(2) 0.0878(19) 0.110(2) -0.0011(14) -0.0092(16) -0.0106(13) _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 N1 N2 1.323(3) . ? N1 C2 1.442(4) . ? N1 C1 1.443(3) . ? N2 O1 1.220(3) . ? C1 C1 1.514(5) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C2 122.1(2) . . ? N2 N1 C1 115.2(2) . . ? C2 N1 C1 122.12(19) . . ? O1 N2 N1 112.8(3) . . ? N1 C1 C1 111.85(16) . 2 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.250 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.039 data_m1 _database_code_depnum_ccdc_archive 'CCDC 829127' #TrackingRef '- cif Complex 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H24 Cl2 Cu N4 O8' _chemical_formula_weight 438.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 8.6311(3) _cell_length_b 13.7336(3) _cell_length_c 15.1029(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.7460(10) _cell_angle_gamma 90.00 _cell_volume 1781.24(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 1.568 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8304 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2786 _reflns_number_gt 2734 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0804P)^2^+0.9710P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.017(13) _refine_ls_number_reflns 2786 _refine_ls_number_parameters 228 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0900 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _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 0.0875(10) 0.6382(4) 0.9503(5) 0.071(2) Uani 1 1 d . . . H1A H 0.1534 0.5945 0.9866 0.106 Uiso 1 1 calc R . . H1B H 0.0177 0.6014 0.9096 0.106 Uiso 1 1 calc R . . H1C H 0.0284 0.6772 0.9876 0.106 Uiso 1 1 calc R . . C2 C 0.2981(7) 0.7663(4) 0.9552(4) 0.0691(14) Uani 1 1 d . . . H2A H 0.3196 0.8246 0.9224 0.083 Uiso 1 1 calc R . . H2B H 0.2543 0.7855 1.0093 0.083 Uiso 1 1 calc R . . C3 C 0.4428(7) 0.7109(4) 0.9774(3) 0.0695(14) Uani 1 1 d . . . H3A H 0.5206 0.7521 1.0094 0.083 Uiso 1 1 calc R . . H3B H 0.4231 0.6560 1.0152 0.083 Uiso 1 1 calc R . . C4 C 0.6273(7) 0.6060(4) 0.9155(4) 0.0614(13) Uani 1 1 d . . . H4A H 0.7058 0.6350 0.9568 0.092 Uiso 1 1 calc R . . H4B H 0.6717 0.5889 0.8619 0.092 Uiso 1 1 calc R . . H4C H 0.5874 0.5486 0.9415 0.092 Uiso 1 1 calc R . . C5 C 0.5384(7) 0.6418(3) 0.6759(4) 0.0501(12) Uani 1 1 d . . . H5A H 0.6007 0.6065 0.6375 0.075 Uiso 1 1 calc R . . H5B H 0.6051 0.6760 0.7200 0.075 Uiso 1 1 calc R . . H5C H 0.4736 0.6876 0.6413 0.075 Uiso 1 1 calc R . . C6 C 0.3290(5) 0.5208(3) 0.6544(3) 0.0448(9) Uani 1 1 d . . . H6A H 0.3053 0.4571 0.6774 0.054 Uiso 1 1 calc R . . H6B H 0.3753 0.5119 0.5990 0.054 Uiso 1 1 calc R . . C7 C 0.1829(5) 0.5798(3) 0.6384(3) 0.0457(9) Uani 1 1 d . . . H7A H 0.2046 0.6406 0.6094 0.055 Uiso 1 1 calc R . . H7B H 0.1057 0.5443 0.6000 0.055 Uiso 1 1 calc R . . C8 C -0.0110(5) 0.6649(4) 0.7124(3) 0.0516(11) Uani 1 1 d . . . H8A H 0.0239 0.7299 0.7021 0.077 Uiso 1 1 calc R . . H8B H -0.0649 0.6638 0.7650 0.077 Uiso 1 1 calc R . . H8C H -0.0801 0.6438 0.6623 0.077 Uiso 1 1 calc R . . Cl2 Cl 0.32164(14) 0.37711(6) 0.88207(7) 0.0467(3) Uani 1 1 d . . . Cl3 Cl 0.30487(12) 0.89583(7) 0.70391(7) 0.0449(2) Uani 1 1 d . . . Cu1 Cu 0.31073(3) 0.63527(3) 0.81066(3) 0.03071(13) Uani 1 1 d . . . N4 N 0.1232(4) 0.5995(3) 0.7242(2) 0.0374(7) Uani 1 1 d . . . N3 N 0.4396(4) 0.5730(2) 0.7200(2) 0.0361(6) Uani 1 1 d . . . N2 N 0.4996(4) 0.6761(2) 0.8947(2) 0.0419(7) Uani 1 1 d . . . N1 N 0.1847(4) 0.7024(3) 0.8995(2) 0.0434(7) Uani 1 1 d . . . O1 O 0.1546(6) 0.9059(4) 0.6551(4) 0.1053(17) Uani 1 1 d . . . O2 O 0.3121(6) 0.8011(2) 0.7419(3) 0.0802(12) Uani 1 1 d . . . O3 O 0.4236(7) 0.9075(4) 0.6463(4) 0.1025(17) Uani 1 1 d . . . O4 O 0.3213(7) 0.9676(3) 0.7709(3) 0.0971(15) Uani 1 1 d . . . O5 O 0.3325(9) 0.3248(4) 0.9605(3) 0.119(2) Uani 1 1 d . . . O6 O 0.4700(8) 0.3757(3) 0.8422(5) 0.0993(18) Uani 1 1 d . . . O7 O 0.2899(6) 0.4758(3) 0.8908(4) 0.1000(16) Uani 1 1 d . . . O8 O 0.2235(10) 0.3324(7) 0.8158(5) 0.153(3) Uani 1 1 d . . . H1 H 0.116(6) 0.743(3) 0.875(3) 0.043(12) Uiso 1 1 d . . . H2 H 0.523(7) 0.727(4) 0.872(3) 0.056(14) Uiso 1 1 d . . . H3 H 0.492(6) 0.532(4) 0.749(3) 0.044(12) Uiso 1 1 d . . . H4 H 0.097(6) 0.563(4) 0.742(3) 0.034(13) 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 0.077(5) 0.073(4) 0.069(4) 0.022(2) 0.037(4) 0.023(3) C2 0.083(4) 0.066(3) 0.058(3) -0.024(2) 0.007(3) 0.013(3) C3 0.067(3) 0.090(4) 0.050(3) -0.023(2) -0.001(2) 0.000(3) C4 0.045(3) 0.072(3) 0.063(3) -0.002(2) -0.015(2) 0.000(3) C5 0.044(3) 0.050(3) 0.060(3) -0.0010(17) 0.023(3) -0.0029(18) C6 0.050(2) 0.043(2) 0.0417(19) -0.0111(14) 0.0045(17) -0.0003(18) C7 0.043(2) 0.053(2) 0.0396(18) -0.0020(16) 0.0004(16) -0.008(2) C8 0.032(2) 0.049(2) 0.071(3) 0.001(2) -0.002(2) -0.003(2) Cl2 0.0582(7) 0.0290(4) 0.0529(5) 0.0041(3) 0.0054(5) 0.0029(4) Cl3 0.0513(6) 0.0283(4) 0.0563(5) 0.0038(4) 0.0109(4) -0.0003(4) Cu1 0.0278(2) 0.0289(2) 0.0357(2) -0.00398(15) 0.00479(14) -0.00062(16) N4 0.035(2) 0.0337(17) 0.0430(17) 0.0039(14) 0.0023(14) -0.0052(15) N3 0.0319(17) 0.0365(16) 0.0410(15) -0.0041(13) 0.0084(13) 0.0031(14) N2 0.040(2) 0.0399(18) 0.0462(17) -0.0067(14) 0.0045(14) -0.0115(15) N1 0.0406(19) 0.0467(18) 0.0435(16) -0.0035(14) 0.0079(14) 0.0136(16) O1 0.079(3) 0.111(4) 0.119(4) 0.017(3) -0.024(3) 0.028(3) O2 0.100(3) 0.0341(17) 0.109(3) 0.0233(18) 0.023(3) 0.0041(17) O3 0.114(4) 0.093(3) 0.113(4) 0.005(3) 0.073(3) -0.024(3) O4 0.137(4) 0.061(2) 0.097(3) -0.032(2) 0.025(3) -0.019(2) O5 0.202(7) 0.086(3) 0.071(3) 0.024(2) 0.022(3) 0.024(4) O6 0.085(4) 0.076(3) 0.143(5) -0.001(3) 0.044(4) 0.020(2) O7 0.107(4) 0.0391(18) 0.159(4) 0.020(2) 0.042(3) 0.022(2) O8 0.171(7) 0.165(6) 0.114(5) -0.007(4) -0.024(5) -0.095(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 C1 N1 1.483(7) . ? C2 C3 1.472(8) . ? C2 N1 1.507(7) . ? C3 N2 1.468(6) . ? C4 N2 1.473(7) . ? C5 N3 1.475(6) . ? C6 N3 1.489(5) . ? C6 C7 1.498(6) . ? C7 N4 1.467(6) . ? C8 N4 1.462(6) . ? Cl2 O5 1.381(5) . ? Cl2 O8 1.388(6) . ? Cl2 O7 1.392(4) . ? Cl2 O6 1.469(6) . ? Cl3 O4 1.409(4) . ? Cl3 O3 1.419(4) . ? Cl3 O2 1.420(3) . ? Cl3 O1 1.433(5) . ? Cu1 N1 2.032(3) . ? Cu1 N4 2.035(4) . ? Cu1 N3 2.037(3) . ? Cu1 N2 2.041(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 C3 C2 N1 108.4(4) . . ? N2 C3 C2 108.8(4) . . ? N3 C6 C7 108.7(3) . . ? N4 C7 C6 108.8(3) . . ? O5 Cl2 O8 111.9(4) . . ? O5 Cl2 O7 115.0(4) . . ? O8 Cl2 O7 112.8(5) . . ? O5 Cl2 O6 111.0(4) . . ? O8 Cl2 O6 101.1(5) . . ? O7 Cl2 O6 103.8(3) . . ? O4 Cl3 O3 109.6(3) . . ? O4 Cl3 O2 110.7(3) . . ? O3 Cl3 O2 110.2(3) . . ? O4 Cl3 O1 108.8(4) . . ? O3 Cl3 O1 110.2(4) . . ? O2 Cl3 O1 107.3(3) . . ? N1 Cu1 N4 95.13(15) . . ? N1 Cu1 N3 177.81(15) . . ? N4 Cu1 N3 85.41(14) . . ? N1 Cu1 N2 84.95(15) . . ? N4 Cu1 N2 177.73(16) . . ? N3 Cu1 N2 94.43(14) . . ? C8 N4 C7 110.5(3) . . ? C8 N4 Cu1 120.0(3) . . ? C7 N4 Cu1 106.5(3) . . ? C5 N3 C6 111.7(4) . . ? C5 N3 Cu1 114.5(3) . . ? C6 N3 Cu1 107.0(2) . . ? C3 N2 C4 109.7(4) . . ? C3 N2 Cu1 107.7(3) . . ? C4 N2 Cu1 119.2(3) . . ? C1 N1 C2 115.3(5) . . ? C1 N1 Cu1 116.1(3) . . ? C2 N1 Cu1 105.8(3) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.556 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.071 # Attachment '- cif Complex 2.cif' data_complex2 _database_code_depnum_ccdc_archive 'CCDC 829128' #TrackingRef '- cif Complex 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H36 Cl2 Cu N4 O10' _chemical_formula_weight 530.89 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' 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' 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' _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 7.3704(5) _cell_length_b 9.9384(7) _cell_length_c 16.4246(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.915(4) _cell_angle_gamma 90.00 _cell_volume 1144.77(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7219 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28.33 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 558 _exptl_absorpt_coefficient_mu 1.240 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14599 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.36 _reflns_number_total 2846 _reflns_number_gt 2491 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.5698P] 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 2846 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 1.0000 1.0000 1.0000 0.03010(13) Uani 1 2 d S . . O5 O 1.2000(3) 1.0793(3) 0.90166(14) 0.0592(5) Uani 1 1 d . . . N1 N 0.8110(3) 0.89689(19) 0.89999(11) 0.0360(4) Uani 1 1 d . . . N2 N 0.8337(2) 1.16276(18) 0.95532(11) 0.0338(4) Uani 1 1 d . . . C3 C 0.6406(4) 0.9848(3) 0.86954(18) 0.0480(6) Uani 1 1 d . . . H3A H 0.5627 0.9767 0.9074 0.058 Uiso 1 1 calc R . . H3B H 0.5644 0.9579 0.8125 0.058 Uiso 1 1 calc R . . C4 C 0.7062(3) 1.1276(3) 0.86844(14) 0.0465(5) Uani 1 1 d . . . H4A H 0.7744 1.1372 0.8268 0.056 Uiso 1 1 calc R . . H4B H 0.5972 1.1875 0.8525 0.056 Uiso 1 1 calc R . . C1 C 0.6163(5) 0.6904(3) 0.83798(18) 0.0642(8) Uani 1 1 d . . . H1A H 0.4958 0.7358 0.8251 0.096 Uiso 1 1 calc R . . H1B H 0.6004 0.5976 0.8505 0.096 Uiso 1 1 calc R . . H1C H 0.6633 0.6962 0.7897 0.096 Uiso 1 1 calc R . . C2 C 0.7583(4) 0.7564(3) 0.91522(15) 0.0484(5) Uani 1 1 d . . . H2A H 0.7044 0.7569 0.9622 0.058 Uiso 1 1 calc R . . H2B H 0.8733 0.7022 0.9326 0.058 Uiso 1 1 calc R . . C6 C 0.6482(4) 1.3560(3) 0.9879(2) 0.0623(7) Uani 1 1 d . . . H6A H 0.7495 1.4159 0.9867 0.093 Uiso 1 1 calc R . . H6B H 0.5899 1.3873 1.0292 0.093 Uiso 1 1 calc R . . H6C H 0.5546 1.3534 0.9323 0.093 Uiso 1 1 calc R . . C5 C 0.7279(3) 1.2163(2) 1.01216(15) 0.0438(5) Uani 1 1 d . . . H5A H 0.8128 1.2182 1.0705 0.053 Uiso 1 1 calc R . . H5B H 0.6237 1.1556 1.0105 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.96076(11) 0.93158(6) 0.68905(4) 0.05368(19) Uani 1 1 d . . . O1 O 0.8037(7) 0.8688(7) 0.6961(4) 0.201(3) Uani 1 1 d . . . O2 O 0.9267(6) 1.0698(3) 0.6901(2) 0.1222(13) Uani 1 1 d . . . O3 O 0.9816(7) 0.8895(5) 0.6133(2) 0.168(2) Uani 1 1 d . . . O4 O 1.1112(6) 0.8936(3) 0.7607(2) 0.1346(15) Uani 1 1 d . . . H6O H 1.193(7) 1.034(5) 0.862(3) 0.082(13) Uiso 1 1 d . . . H5O H 1.193(5) 1.157(4) 0.880(2) 0.068(11) Uiso 1 1 d . . . H1N H 0.864(3) 0.893(3) 0.8605(16) 0.037(6) Uiso 1 1 d . . . H2N H 0.905(4) 1.223(3) 0.9514(17) 0.044(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0256(2) 0.0346(2) 0.02649(19) -0.00063(11) 0.00261(13) 0.00385(12) O5 0.0623(12) 0.0673(13) 0.0474(10) -0.0007(10) 0.0161(9) 0.0064(10) N1 0.0336(9) 0.0431(9) 0.0280(8) -0.0014(7) 0.0044(7) -0.0007(7) N2 0.0315(8) 0.0356(8) 0.0322(8) 0.0044(7) 0.0069(6) 0.0030(7) C3 0.0338(11) 0.0550(13) 0.0442(13) -0.0021(10) -0.0041(10) 0.0030(9) C4 0.0440(12) 0.0517(12) 0.0336(10) 0.0068(9) -0.0029(9) 0.0091(10) C1 0.0711(18) 0.0592(16) 0.0500(14) -0.0103(12) 0.0005(13) -0.0219(14) C2 0.0537(13) 0.0465(12) 0.0377(11) -0.0030(9) 0.0034(10) -0.0111(10) C6 0.0665(17) 0.0479(14) 0.0726(18) 0.0046(13) 0.0218(15) 0.0202(13) C5 0.0437(11) 0.0422(11) 0.0494(12) 0.0048(9) 0.0200(10) 0.0100(9) Cl1 0.0775(4) 0.0457(3) 0.0405(3) -0.0044(2) 0.0221(3) 0.0030(3) O1 0.137(3) 0.250(7) 0.225(6) 0.062(5) 0.070(4) -0.059(4) O2 0.187(4) 0.0619(16) 0.101(2) -0.0051(15) 0.019(2) 0.031(2) O3 0.248(5) 0.187(4) 0.0665(18) -0.024(2) 0.047(2) 0.122(4) O4 0.175(3) 0.095(2) 0.0822(19) -0.0144(16) -0.038(2) 0.047(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 2.0258(17) 3_777 ? Cu1 N2 2.0258(17) . ? Cu1 N1 2.0690(17) . ? Cu1 N1 2.0690(17) 3_777 ? O5 H6O 0.79(5) . ? O5 H5O 0.84(4) . ? N1 C3 1.485(3) . ? N1 C2 1.491(3) . ? N1 H1N 0.85(3) . ? N2 C5 1.487(3) . ? N2 C4 1.489(3) . ? N2 H2N 0.81(3) . ? C3 C4 1.501(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C1 C2 1.522(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C6 C5 1.512(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? Cl1 O1 1.351(4) . ? Cl1 O3 1.365(3) . ? Cl1 O2 1.398(3) . ? Cl1 O4 1.398(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 N2 Cu1 N2 180.000(1) 3_777 . ? N2 Cu1 N1 94.40(7) 3_777 . ? N2 Cu1 N1 85.60(7) . . ? N2 Cu1 N1 85.60(7) 3_777 3_777 ? N2 Cu1 N1 94.40(7) . 3_777 ? N1 Cu1 N1 180.000(1) . 3_777 ? H6O O5 H5O 101(4) . . ? C3 N1 C2 111.73(19) . . ? C3 N1 Cu1 105.62(14) . . ? C2 N1 Cu1 118.50(13) . . ? C3 N1 H1N 107.8(17) . . ? C2 N1 H1N 107.0(17) . . ? Cu1 N1 H1N 105.7(17) . . ? C5 N2 C4 112.80(18) . . ? C5 N2 Cu1 115.72(13) . . ? C4 N2 Cu1 107.02(14) . . ? C5 N2 H2N 105.5(19) . . ? C4 N2 H2N 109.4(19) . . ? Cu1 N2 H2N 106(2) . . ? N1 C3 C4 108.53(19) . . ? N1 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? N1 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? N2 C4 C3 108.75(19) . . ? N2 C4 H4A 109.9 . . ? C3 C4 H4A 109.9 . . ? N2 C4 H4B 109.9 . . ? C3 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C1 114.3(2) . . ? N1 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? N1 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C5 C6 113.5(2) . . ? N2 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? N2 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? O1 Cl1 O3 106.0(4) . . ? O1 Cl1 O2 106.9(4) . . ? O3 Cl1 O2 112.5(2) . . ? O1 Cl1 O4 106.4(3) . . ? O3 Cl1 O4 113.7(2) . . ? O2 Cl1 O4 110.7(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.712 _refine_diff_density_min -0.645 _refine_diff_density_rms 0.104 # Attachment '- cif Complex 3.cif' data_complex3 _database_code_depnum_ccdc_archive 'CCDC 829129' #TrackingRef '- cif Complex 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H48 Cl2 Cu N4 O8' _chemical_formula_weight 607.06 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' 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 14.8346(5) _cell_length_b 16.8936(6) _cell_length_c 24.3560(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6103.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5078 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 28.31 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2584 _exptl_absorpt_coefficient_mu 0.935 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50935 _diffrn_reflns_av_R_equivalents 0.0686 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.31 _reflns_number_total 7590 _reflns_number_gt 3567 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0564P)^2^+2.2776P] 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 7590 _refine_ls_number_parameters 324 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1379 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1508 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.002 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 0.2515(4) 0.9621(4) 0.5181(2) 0.145(2) Uani 1 1 d . . . H1A H 0.2370 1.0070 0.4956 0.217 Uiso 1 1 calc R . . H1B H 0.1969 0.9378 0.5309 0.217 Uiso 1 1 calc R . . H1C H 0.2853 0.9245 0.4969 0.217 Uiso 1 1 calc R . . C2 C 0.3948(4) 1.0175(5) 0.5504(3) 0.202(4) Uani 1 1 d . . . H2A H 0.4303 0.9740 0.5371 0.303 Uiso 1 1 calc R . . H2B H 0.4245 1.0414 0.5812 0.303 Uiso 1 1 calc R . . H2C H 0.3877 1.0560 0.5217 0.303 Uiso 1 1 calc R . . C3 C 0.3077(4) 0.9890(3) 0.56699(18) 0.0995(15) Uani 1 1 d . . . H3A H 0.2758 1.0336 0.5839 0.119 Uiso 1 1 calc R . . C4 C 0.3078(3) 0.9215(2) 0.60853(15) 0.0680(10) Uani 1 1 d . . . H4A H 0.2460 0.9114 0.6196 0.082 Uiso 1 1 calc R . . H4B H 0.3299 0.8742 0.5904 0.082 Uiso 1 1 calc R . . C5 C 0.3206(3) 0.9972(2) 0.69291(15) 0.0694(11) Uani 1 1 d . . . H5A H 0.2590 0.9828 0.7016 0.083 Uiso 1 1 calc R . . H5B H 0.3197 1.0470 0.6731 0.083 Uiso 1 1 calc R . . C6 C 0.3740(3) 1.00592(19) 0.74453(15) 0.0648(10) Uani 1 1 d . . . H6A H 0.4334 1.0266 0.7361 0.078 Uiso 1 1 calc R . . H6B H 0.3442 1.0429 0.7690 0.078 Uiso 1 1 calc R . . C7 C 0.4570(3) 0.9259(2) 0.81266(15) 0.0627(10) Uani 1 1 d . . . H7A H 0.5132 0.9354 0.7934 0.075 Uiso 1 1 calc R . . H7B H 0.4600 0.8728 0.8277 0.075 Uiso 1 1 calc R . . C8 C 0.4518(3) 0.9832(2) 0.85994(17) 0.0697(11) Uani 1 1 d . . . H8 H 0.4447 1.0366 0.8448 0.084 Uiso 1 1 calc R . . C9 C 0.3743(4) 0.9677(4) 0.8968(2) 0.138(2) Uani 1 1 d . . . H9A H 0.3191 0.9737 0.8767 0.208 Uiso 1 1 calc R . . H9B H 0.3753 1.0045 0.9268 0.208 Uiso 1 1 calc R . . H9C H 0.3782 0.9147 0.9108 0.208 Uiso 1 1 calc R . . C10 C 0.5399(3) 0.9809(3) 0.8918(2) 0.1144(18) Uani 1 1 d . . . H10A H 0.5374 1.0184 0.9213 0.172 Uiso 1 1 calc R . . H10B H 0.5888 0.9941 0.8677 0.172 Uiso 1 1 calc R . . H10C H 0.5490 0.9287 0.9064 0.172 Uiso 1 1 calc R . . C11 C 0.5489(3) 0.7486(3) 0.51435(19) 0.1196(18) Uani 1 1 d . . . H11A H 0.5533 0.7099 0.4856 0.179 Uiso 1 1 calc R . . H11B H 0.6075 0.7573 0.5300 0.179 Uiso 1 1 calc R . . H11C H 0.5264 0.7973 0.4995 0.179 Uiso 1 1 calc R . . C12 C 0.3929(4) 0.7016(4) 0.5352(2) 0.125(2) Uani 1 1 d . . . H12A H 0.3673 0.7496 0.5210 0.187 Uiso 1 1 calc R . . H12B H 0.3544 0.6807 0.5634 0.187 Uiso 1 1 calc R . . H12C H 0.3985 0.6636 0.5061 0.187 Uiso 1 1 calc R . . C13 C 0.4844(3) 0.7186(3) 0.55893(17) 0.0845(13) Uani 1 1 d . . . H13 H 0.5088 0.6692 0.5738 0.101 Uiso 1 1 calc R . . C14 C 0.4816(3) 0.7794(2) 0.60513(15) 0.0696(11) Uani 1 1 d . . . H14A H 0.5423 0.7864 0.6190 0.083 Uiso 1 1 calc R . . H14B H 0.4624 0.8296 0.5898 0.083 Uiso 1 1 calc R . . C15 C 0.4591(3) 0.6919(2) 0.68322(16) 0.0768(12) Uani 1 1 d . . . H15A H 0.4580 0.6449 0.6604 0.092 Uiso 1 1 calc R . . H15B H 0.5212 0.7024 0.6934 0.092 Uiso 1 1 calc R . . C16 C 0.4046(3) 0.6783(2) 0.73323(16) 0.0686(11) Uani 1 1 d . . . H16A H 0.3441 0.6623 0.7231 0.082 Uiso 1 1 calc R . . H16B H 0.4314 0.6364 0.7550 0.082 Uiso 1 1 calc R . . C17 C 0.3267(3) 0.7491(2) 0.80654(15) 0.0642(10) Uani 1 1 d . . . H17A H 0.2700 0.7499 0.7867 0.077 Uiso 1 1 calc R . . H17B H 0.3294 0.7972 0.8282 0.077 Uiso 1 1 calc R . . C18 C 0.3248(3) 0.6794(2) 0.84576(16) 0.0689(11) Uani 1 1 d . . . H18 H 0.3215 0.6307 0.8240 0.083 Uiso 1 1 calc R . . C19 C 0.4085(3) 0.6753(3) 0.88141(18) 0.0984(16) Uani 1 1 d . . . H19A H 0.4604 0.6660 0.8587 0.148 Uiso 1 1 calc R . . H19B H 0.4024 0.6329 0.9074 0.148 Uiso 1 1 calc R . . H19C H 0.4159 0.7244 0.9007 0.148 Uiso 1 1 calc R . . C20 C 0.2398(3) 0.6853(3) 0.8806(2) 0.125(2) Uani 1 1 d . . . H20A H 0.2348 0.6392 0.9034 0.187 Uiso 1 1 calc R . . H20B H 0.1880 0.6885 0.8570 0.187 Uiso 1 1 calc R . . H20C H 0.2428 0.7317 0.9032 0.187 Uiso 1 1 calc R . . H1 H 0.4086 0.9515 0.6433 0.187 Uiso 1 1 d R . . H2 H 0.3426 0.9188 0.7843 0.187 Uiso 1 1 d R . . H3 H 0.3738 0.7501 0.6404 0.187 Uiso 1 1 d R . . H4 H 0.4432 0.7538 0.7796 0.187 Uiso 1 1 d R . . Cl1 Cl 0.61638(7) 0.93215(6) 0.68054(5) 0.0780(3) Uani 1 1 d . . . Cl2 Cl 0.16518(7) 0.74880(6) 0.67163(4) 0.0683(3) Uani 1 1 d . . . Cu1 Cu 0.39313(3) 0.84417(2) 0.710763(16) 0.04811(16) Uani 1 1 d . . . N1 N 0.36241(19) 0.93507(15) 0.65852(11) 0.0540(7) Uani 1 1 d . . . N2 N 0.38244(18) 0.92793(15) 0.77161(11) 0.0506(7) Uani 1 1 d . . . N3 N 0.42217(19) 0.76046(15) 0.65198(11) 0.0566(8) Uani 1 1 d . . . N4 N 0.40103(18) 0.75182(15) 0.76555(11) 0.0519(7) Uani 1 1 d . . . O1 O 0.6506(4) 0.9830(2) 0.72036(19) 0.181(2) Uani 1 1 d . . . O2 O 0.6894(3) 0.8951(3) 0.6580(2) 0.190(2) Uani 1 1 d . . . O3 O 0.56130(19) 0.87231(16) 0.70619(11) 0.0787(8) Uani 1 1 d . . . O4 O 0.5658(2) 0.9743(2) 0.64391(19) 0.1570(18) Uani 1 1 d . . . O5 O 0.0997(2) 0.7868(2) 0.63967(18) 0.1407(15) Uani 1 1 d . . . O6 O 0.1213(3) 0.7025(2) 0.71195(14) 0.1288(14) Uani 1 1 d . . . O7 O 0.2202(2) 0.69937(18) 0.63978(13) 0.1090(11) Uani 1 1 d . . . O8 O 0.22151(18) 0.80762(15) 0.69787(11) 0.0800(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.146(5) 0.202(7) 0.087(3) 0.031(4) -0.036(4) -0.008(5) C2 0.134(6) 0.313(10) 0.158(6) 0.148(7) -0.031(5) -0.087(6) C3 0.105(4) 0.117(4) 0.077(3) 0.029(3) -0.020(3) 0.009(3) C4 0.058(2) 0.078(3) 0.069(3) 0.002(2) -0.008(2) 0.014(2) C5 0.080(3) 0.051(2) 0.077(3) 0.0008(19) -0.010(2) 0.020(2) C6 0.081(3) 0.0428(19) 0.070(3) 0.0042(18) -0.006(2) 0.0033(18) C7 0.066(3) 0.057(2) 0.065(2) -0.0048(19) -0.012(2) 0.0049(19) C8 0.069(3) 0.059(2) 0.081(3) -0.012(2) -0.014(2) 0.005(2) C9 0.119(5) 0.203(7) 0.093(4) -0.056(4) 0.020(4) -0.054(4) C10 0.106(4) 0.103(4) 0.134(4) -0.040(3) -0.056(4) 0.020(3) C11 0.112(4) 0.168(5) 0.079(3) -0.004(3) 0.022(3) 0.024(4) C12 0.130(5) 0.163(5) 0.081(3) -0.041(3) 0.009(3) -0.032(4) C13 0.104(4) 0.088(3) 0.061(3) -0.007(2) 0.008(3) 0.018(3) C14 0.061(3) 0.077(3) 0.071(3) -0.005(2) 0.002(2) 0.014(2) C15 0.099(3) 0.058(2) 0.074(3) -0.002(2) 0.009(3) 0.026(2) C16 0.093(3) 0.0456(19) 0.068(2) -0.0013(18) -0.004(2) 0.011(2) C17 0.062(3) 0.063(2) 0.068(2) 0.0074(19) 0.007(2) 0.003(2) C18 0.072(3) 0.062(2) 0.073(3) 0.010(2) 0.003(2) -0.007(2) C19 0.105(4) 0.115(4) 0.074(3) 0.028(3) -0.011(3) -0.014(3) C20 0.092(4) 0.149(5) 0.132(4) 0.057(4) 0.040(3) 0.001(3) Cl1 0.0465(6) 0.0701(7) 0.1173(9) 0.0092(6) -0.0100(6) -0.0016(6) Cl2 0.0513(6) 0.0600(6) 0.0938(7) 0.0000(5) 0.0013(6) 0.0009(5) Cu1 0.0476(3) 0.0423(2) 0.0545(3) 0.00027(18) -0.0001(2) 0.00549(19) N1 0.0543(18) 0.0507(16) 0.0572(18) 0.0034(14) -0.0047(15) 0.0074(14) N2 0.0501(18) 0.0435(15) 0.0581(17) -0.0014(13) -0.0021(14) 0.0053(13) N3 0.0600(19) 0.0519(17) 0.0580(18) 0.0010(14) 0.0065(15) 0.0118(15) N4 0.0590(19) 0.0416(14) 0.0551(17) -0.0012(13) 0.0027(15) 0.0066(14) O1 0.242(5) 0.116(3) 0.185(4) 0.024(3) -0.100(4) -0.090(3) O2 0.103(3) 0.160(4) 0.308(6) 0.045(4) 0.107(4) 0.028(3) O3 0.0636(18) 0.0777(17) 0.095(2) 0.0067(15) 0.0013(15) -0.0141(15) O4 0.089(2) 0.148(3) 0.234(4) 0.103(3) -0.061(3) -0.025(2) O5 0.109(3) 0.105(3) 0.208(4) -0.004(3) -0.084(3) 0.019(2) O6 0.146(3) 0.100(3) 0.141(3) 0.000(2) 0.054(2) -0.056(2) O7 0.088(2) 0.104(2) 0.135(3) -0.032(2) 0.022(2) 0.0049(19) O8 0.0669(19) 0.0681(16) 0.105(2) 0.0003(16) -0.0071(16) -0.0139(15) _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 C3 1.523(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.437(6) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.524(5) . ? C3 H3A 0.9800 . ? C4 N1 1.480(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.479(4) . ? C5 C6 1.493(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N2 1.479(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N2 1.491(4) . ? C7 C8 1.506(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.482(6) . ? C8 C10 1.520(5) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C13 1.533(6) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.504(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.523(5) . ? C13 H13 0.9800 . ? C14 N3 1.476(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.479(5) . ? C15 N3 1.490(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N4 1.471(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N4 1.488(4) . ? C17 C18 1.516(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.517(5) . ? C18 C20 1.524(6) . ? C18 H18 0.9800 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? Cl1 O4 1.366(3) . ? Cl1 O2 1.366(4) . ? Cl1 O1 1.391(4) . ? Cl1 O3 1.442(3) . ? Cl2 O7 1.402(3) . ? Cl2 O5 1.400(3) . ? Cl2 O6 1.414(3) . ? Cl2 O8 1.447(3) . ? Cu1 N1 2.046(3) . ? Cu1 N2 2.055(3) . ? Cu1 N3 2.058(3) . ? Cu1 N4 2.056(3) . ? N1 H1 0.8266 . ? N2 H2 0.6848 . ? N3 H3 0.7907 . ? N4 H4 0.7134 . ? 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 C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C2 C3 C1 111.8(5) . . ? C2 C3 C4 115.9(4) . . ? C1 C3 C4 107.3(4) . . ? C2 C3 H3A 107.2 . . ? C1 C3 H3A 107.2 . . ? C4 C3 H3A 107.2 . . ? N1 C4 C3 115.5(3) . . ? N1 C4 H4A 108.4 . . ? C3 C4 H4A 108.4 . . ? N1 C4 H4B 108.4 . . ? C3 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? N1 C5 C6 108.9(3) . . ? N1 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? N1 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? N2 C6 C5 109.4(3) . . ? N2 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? N2 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? N2 C7 C8 117.4(3) . . ? N2 C7 H7A 108.0 . . ? C8 C7 H7A 108.0 . . ? N2 C7 H7B 108.0 . . ? C8 C7 H7B 108.0 . . ? H7A C7 H7B 107.2 . . ? C9 C8 C7 112.9(3) . . ? C9 C8 C10 110.7(4) . . ? C7 C8 C10 109.2(3) . . ? C9 C8 H8 107.9 . . ? C7 C8 H8 107.9 . . ? C10 C8 H8 107.9 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13 C11 H11A 109.5 . . ? C13 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C13 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C12 C13 C11 110.8(4) . . ? C12 C13 C14 112.8(4) . . ? C11 C13 C14 108.6(4) . . ? C12 C13 H13 108.2 . . ? C11 C13 H13 108.2 . . ? C14 C13 H13 108.2 . . ? N3 C14 C13 116.2(3) . . ? N3 C14 H14A 108.2 . . ? C13 C14 H14A 108.2 . . ? N3 C14 H14B 108.2 . . ? C13 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? C16 C15 N3 109.8(3) . . ? C16 C15 H15A 109.7 . . ? N3 C15 H15A 109.7 . . ? C16 C15 H15B 109.7 . . ? N3 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? N4 C16 C15 109.3(3) . . ? N4 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? N4 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? N4 C17 C18 117.4(3) . . ? N4 C17 H17A 108.0 . . ? C18 C17 H17A 108.0 . . ? N4 C17 H17B 108.0 . . ? C18 C17 H17B 108.0 . . ? H17A C17 H17B 107.2 . . ? C19 C18 C17 112.4(3) . . ? C19 C18 C20 111.3(4) . . ? C17 C18 C20 108.4(3) . . ? C19 C18 H18 108.2 . . ? C17 C18 H18 108.2 . . ? C20 C18 H18 108.2 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O4 Cl1 O2 114.4(3) . . ? O4 Cl1 O1 109.5(3) . . ? O2 Cl1 O1 105.9(3) . . ? O4 Cl1 O3 109.7(2) . . ? O2 Cl1 O3 107.5(2) . . ? O1 Cl1 O3 109.7(2) . . ? O7 Cl2 O5 111.7(2) . . ? O7 Cl2 O6 108.9(2) . . ? O5 Cl2 O6 108.7(3) . . ? O7 Cl2 O8 108.48(19) . . ? O5 Cl2 O8 109.36(19) . . ? O6 Cl2 O8 109.79(19) . . ? N1 Cu1 N2 85.09(11) . . ? N1 Cu1 N3 97.45(11) . . ? N2 Cu1 N3 172.29(11) . . ? N1 Cu1 N4 170.35(11) . . ? N2 Cu1 N4 93.37(11) . . ? N3 Cu1 N4 85.31(11) . . ? C4 N1 C5 110.2(3) . . ? C4 N1 Cu1 121.2(2) . . ? C5 N1 Cu1 105.9(2) . . ? C4 N1 H1 97.9 . . ? C5 N1 H1 111.3 . . ? Cu1 N1 H1 110.2 . . ? C6 N2 C7 112.5(3) . . ? C6 N2 Cu1 107.4(2) . . ? C7 N2 Cu1 114.2(2) . . ? C6 N2 H2 109.3 . . ? C7 N2 H2 109.5 . . ? Cu1 N2 H2 103.6 . . ? C14 N3 C15 110.1(3) . . ? C14 N3 Cu1 120.9(2) . . ? C15 N3 Cu1 104.8(2) . . ? C14 N3 H3 108.3 . . ? C15 N3 H3 110.1 . . ? Cu1 N3 H3 102.2 . . ? C16 N4 C17 111.1(3) . . ? C16 N4 Cu1 107.2(2) . . ? C17 N4 Cu1 114.6(2) . . ? C16 N4 H4 105.3 . . ? C17 N4 H4 109.2 . . ? Cu1 N4 H4 109.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.522 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.060 # Attachment '- cif T-3.cif' data_m3 _database_code_depnum_ccdc_archive 'CCDC 854586' #TrackingRef '- cif T-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H36 N2 O4 S2' _chemical_formula_weight 480.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3633(2) _cell_length_b 9.9606(5) _cell_length_c 12.5886(5) _cell_angle_alpha 91.902(3) _cell_angle_beta 98.241(3) _cell_angle_gamma 97.192(3) _cell_volume 659.43(5) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2376 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 23.74 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 258 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6527 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2151 _reflns_number_gt 1545 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2151 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 S1 S -0.18105(10) 0.56669(6) 0.20710(4) 0.0560(3) Uani 1 1 d . . . O1 O -0.3572(3) 0.49575(17) 0.26746(12) 0.0768(5) Uani 1 1 d . . . O2 O -0.2623(3) 0.66470(15) 0.13386(12) 0.0699(5) Uani 1 1 d . . . N1 N -0.0733(3) 0.45228(16) 0.13708(12) 0.0477(5) Uani 1 1 d . . . C1 C 0.7293(6) 0.8350(3) 0.5170(3) 0.1210(12) Uani 1 1 d . . . H1A H 0.7628 0.9294 0.5036 0.181 Uiso 1 1 calc R . . H1B H 0.8732 0.7908 0.5056 0.181 Uiso 1 1 calc R . . H1C H 0.6992 0.8256 0.5899 0.181 Uiso 1 1 calc R . . C2 C 0.4967(5) 0.7704(3) 0.4410(2) 0.0723(7) Uani 1 1 d . . . C3 C 0.4261(5) 0.8231(3) 0.3434(2) 0.0800(8) Uani 1 1 d . . . H3 H 0.5214 0.9007 0.3244 0.096 Uiso 1 1 calc R . . C4 C 0.2176(5) 0.7639(2) 0.27262(19) 0.0674(7) Uani 1 1 d . . . H4 H 0.1726 0.8025 0.2076 0.081 Uiso 1 1 calc R . . C5 C 0.0767(4) 0.6480(2) 0.29831(15) 0.0479(5) Uani 1 1 d . . . C7 C 0.3544(5) 0.6549(3) 0.46552(19) 0.0734(7) Uani 1 1 d . . . H7 H 0.3983 0.6173 0.5312 0.088 Uiso 1 1 calc R . . C6 C 0.1478(5) 0.5928(2) 0.39561(18) 0.0632(6) Uani 1 1 d . . . H6 H 0.0559 0.5136 0.4139 0.076 Uiso 1 1 calc R . . C12 C -0.3882(5) 0.1891(3) 0.0752(3) 0.1199(12) Uani 1 1 d . . . H15A H -0.4364 0.1138 0.0236 0.180 Uiso 1 1 calc R . . H12B H -0.4273 0.2709 0.0420 0.180 Uiso 1 1 calc R . . H12C H -0.4799 0.1750 0.1348 0.180 Uiso 1 1 calc R . . C10 C -0.1101(5) 0.2011(2) 0.1140(2) 0.0738(7) Uani 1 1 d . . . H10A H -0.0225 0.2088 0.0508 0.089 Uiso 1 1 calc R . . C11 C -0.0370(6) 0.0771(3) 0.1705(3) 0.1078(10) Uani 1 1 d . . . H11A H 0.1438 0.0872 0.1916 0.162 Uiso 1 1 calc R . . H11B H -0.0889 -0.0017 0.1227 0.162 Uiso 1 1 calc R . . H11C H -0.1197 0.0669 0.2331 0.162 Uiso 1 1 calc R . . C9 C -0.0142(4) 0.3272(2) 0.18743(16) 0.0574(6) Uani 1 1 d . . . H9A H -0.0904 0.3193 0.2527 0.069 Uiso 1 1 calc R . . H9B H 0.1684 0.3324 0.2073 0.069 Uiso 1 1 calc R . . C8 C 0.0816(3) 0.5022(2) 0.05476(13) 0.0472(5) Uani 1 1 d . . . H8B H 0.2165 0.4465 0.0512 0.057 Uiso 1 1 calc R . . H8A H 0.1593 0.5945 0.0748 0.057 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 S1 0.0538(4) 0.0680(5) 0.0473(4) -0.0052(3) 0.0068(3) 0.0146(3) O1 0.0601(9) 0.1050(14) 0.0667(10) -0.0073(10) 0.0258(8) 0.0003(9) O2 0.0762(11) 0.0778(12) 0.0588(9) 0.0024(9) -0.0045(8) 0.0389(9) N1 0.0563(10) 0.0474(11) 0.0403(10) 0.0008(9) 0.0075(8) 0.0112(8) C1 0.094(2) 0.128(3) 0.124(2) -0.051(2) -0.023(2) 0.0096(19) C2 0.0732(17) 0.0683(19) 0.0701(19) -0.0205(16) -0.0041(14) 0.0122(15) C3 0.099(2) 0.0541(17) 0.081(2) -0.0088(16) 0.0134(17) -0.0061(14) C4 0.0944(19) 0.0504(16) 0.0548(15) -0.0003(13) 0.0026(14) 0.0102(14) C5 0.0595(13) 0.0459(14) 0.0406(13) 0.0002(11) 0.0104(10) 0.0132(11) C7 0.0899(19) 0.082(2) 0.0472(15) -0.0014(15) -0.0047(14) 0.0256(17) C6 0.0779(16) 0.0655(17) 0.0439(14) 0.0022(13) 0.0056(12) 0.0042(13) C12 0.089(2) 0.075(2) 0.176(3) -0.002(2) -0.032(2) -0.0063(17) C10 0.0782(18) 0.0520(16) 0.0874(18) 0.0067(15) -0.0026(15) 0.0102(13) C11 0.116(2) 0.0596(19) 0.142(3) 0.0190(19) -0.003(2) 0.0102(16) C9 0.0607(13) 0.0597(16) 0.0498(13) 0.0062(12) 0.0026(11) 0.0059(12) C8 0.0492(11) 0.0507(13) 0.0408(11) -0.0013(10) 0.0047(9) 0.0071(10) _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 S1 O1 1.4296(15) . ? S1 O2 1.4298(15) . ? S1 N1 1.6291(16) . ? S1 C5 1.757(2) . ? N1 C9 1.466(2) . ? N1 C8 1.479(2) . ? C1 C2 1.517(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C7 1.369(3) . ? C2 C3 1.374(3) . ? C3 C4 1.381(3) . ? C3 H3 0.9300 . ? C4 C5 1.373(3) . ? C4 H4 0.9300 . ? C5 C6 1.383(3) . ? C7 C6 1.378(3) . ? C7 H7 0.9300 . ? C6 H6 0.9300 . ? C12 C10 1.490(3) . ? C12 H15A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C10 C11 1.512(3) . ? C10 C9 1.524(3) . ? C10 H10A 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C8 C8 1.520(3) 2_565 ? C8 H8B 0.9700 . ? C8 H8A 0.9700 . ? 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 S1 O2 120.10(10) . . ? O1 S1 N1 106.68(9) . . ? O2 S1 N1 106.71(9) . . ? O1 S1 C5 108.00(9) . . ? O2 S1 C5 107.45(10) . . ? N1 S1 C5 107.29(9) . . ? C9 N1 C8 117.00(15) . . ? C9 N1 S1 118.92(13) . . ? C8 N1 S1 116.52(13) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 C3 117.5(2) . . ? C7 C2 C1 121.2(3) . . ? C3 C2 C1 121.2(3) . . ? C2 C3 C4 121.8(3) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 120.0(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 118.8(2) . . ? C4 C5 S1 120.82(17) . . ? C6 C5 S1 120.33(18) . . ? C2 C7 C6 121.8(2) . . ? C2 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C6 C5 120.1(2) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C10 C12 H15A 109.5 . . ? C10 C12 H12B 109.5 . . ? H15A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H15A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C12 C10 C11 112.1(2) . . ? C12 C10 C9 112.5(2) . . ? C11 C10 C9 109.6(2) . . ? C12 C10 H10A 107.5 . . ? C11 C10 H10A 107.5 . . ? C9 C10 H10A 107.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C9 C10 112.73(17) . . ? N1 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N1 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? N1 C8 C8 110.69(19) . 2_565 ? N1 C8 H8B 109.5 . . ? C8 C8 H8B 109.5 2_565 . ? N1 C8 H8A 109.5 . . ? C8 C8 H8A 109.5 2_565 . ? H8B C8 H8A 108.1 . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.224 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.038