Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Duan Chun-ying' _publ_contact_author_address ; Nanjing University, Coordination Chemistry Institute Nanjing 210093 CHINA ; _publ_contact_author_email DUANCY@NJU.EDU.CN _publ_section_title ; Chiral aggregation and spontaneous resolution of thiosemicarbazone metal complexes ; loop_ _publ_author_name 'Duan Chun-ying' 'Ming-xue Li' 'Qing-Jin Meng' 'Bing-guang Zhang' # Attachment 'compound1.cif' data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 271335' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Mn N10 O0 S2' _chemical_formula_weight 443.43 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+1/4' 'y+1/2, -x+1/2, z+3/4' '-x+1/2, y+1/2, -z+1/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 10.9088(18) _cell_length_b 10.9088(18) _cell_length_c 22.362(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2661.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7893 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 28.22 _exptl_crystal_description block _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.107 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 0.669 _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 293(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_reflns_number 12952 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2330 _reflns_number_gt 2246 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1450P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.13(3) _refine_ls_number_reflns 2330 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1626 _refine_ls_wR_factor_gt 0.1614 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 Mn1 Mn 0.67433(4) 0.67433(4) 0.0000 0.0424(3) Uani 1 2 d S . . S1 S 0.64920(10) 0.89879(8) 0.02108(4) 0.0581(3) Uani 1 1 d . . . N1 N 0.5879(4) 0.9869(3) 0.12647(17) 0.0678(10) Uani 1 1 d . . . H1A H 0.5654 0.9828 0.1633 0.081 Uiso 1 1 calc R . . H1B H 0.5980 1.0571 0.1097 0.081 Uiso 1 1 calc R . . N2 N 0.5888(3) 0.7814(3) 0.12605(13) 0.0527(7) Uani 1 1 d . . . N3 N 0.6113(3) 0.6768(3) 0.09496(12) 0.0442(6) Uani 1 1 d . . . N4 N 0.6542(3) 0.4751(3) 0.03199(14) 0.0537(8) Uani 1 1 d . . . N5 N 0.6193(4) 0.2448(3) 0.0803(2) 0.0752(11) Uani 1 1 d . . . C1 C 0.6074(4) 0.8836(3) 0.09519(16) 0.0502(8) Uani 1 1 d . . . C2 C 0.5935(3) 0.5742(3) 0.12299(14) 0.0483(8) Uani 1 1 d . . . C3 C 0.5554(5) 0.5662(5) 0.18740(16) 0.0763(13) Uani 1 1 d . . . H3A H 0.5655 0.6448 0.2061 0.114 Uiso 1 1 calc R . . H3B H 0.6053 0.5068 0.2076 0.114 Uiso 1 1 calc R . . H3C H 0.4709 0.5419 0.1897 0.114 Uiso 1 1 calc R . . C4 C 0.6155(3) 0.4625(3) 0.08906(16) 0.0489(8) Uani 1 1 d . . . C5 C 0.5995(4) 0.3446(3) 0.1118(2) 0.0604(10) Uani 1 1 d . . . H5A H 0.5735 0.3361 0.1512 0.073 Uiso 1 1 calc R . . C6 C 0.6575(5) 0.2590(4) 0.0246(2) 0.0748(13) Uani 1 1 d . . . H6A H 0.6720 0.1901 0.0012 0.090 Uiso 1 1 calc R . . C7 C 0.6762(4) 0.3730(4) 0.0009(2) 0.0719(12) Uani 1 1 d . . . H7A H 0.7051 0.3797 -0.0381 0.086 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 Mn1 0.0466(3) 0.0466(3) 0.0342(4) 0.0003(2) -0.0003(2) -0.0073(3) S1 0.0843(7) 0.0432(5) 0.0468(5) 0.0056(4) 0.0008(4) -0.0089(4) N1 0.106(3) 0.0409(17) 0.056(2) -0.0040(15) -0.002(2) 0.0030(17) N2 0.070(2) 0.0431(16) 0.0447(15) -0.0013(13) 0.0009(15) 0.0018(14) N3 0.0537(15) 0.0398(14) 0.0393(14) 0.0027(12) 0.0013(12) -0.0002(12) N4 0.0641(19) 0.0460(16) 0.0509(17) -0.0005(13) 0.0044(15) -0.0039(13) N5 0.089(3) 0.0431(18) 0.094(3) 0.0091(19) -0.016(2) -0.0090(17) C1 0.060(2) 0.0467(18) 0.0437(18) 0.0016(15) -0.0049(16) -0.0006(15) C2 0.0536(19) 0.049(2) 0.0419(16) 0.0046(15) 0.0086(15) -0.0002(14) C3 0.108(4) 0.069(3) 0.052(2) 0.014(2) 0.026(2) 0.010(2) C4 0.0500(18) 0.0438(18) 0.053(2) 0.0102(15) -0.0018(16) -0.0030(14) C5 0.073(2) 0.046(2) 0.063(2) 0.0110(17) 0.000(2) -0.0051(17) C6 0.100(4) 0.048(2) 0.076(3) -0.007(2) 0.001(3) 0.000(2) C7 0.101(3) 0.054(2) 0.060(2) -0.008(2) 0.002(3) 0.002(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 Mn1 N3 2.232(3) 7 ? Mn1 N3 2.232(3) . ? Mn1 N4 2.299(3) 7 ? Mn1 N4 2.299(3) . ? Mn1 S1 2.5086(11) 7 ? Mn1 S1 2.5086(11) . ? S1 C1 1.727(4) . ? N1 C1 1.343(5) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 C1 1.327(5) . ? N2 N3 1.358(4) . ? N3 C2 1.298(4) . ? N4 C7 1.335(6) . ? N4 C4 1.351(5) . ? N5 C5 1.314(6) . ? N5 C6 1.321(7) . ? C2 C4 1.455(5) . ? C2 C3 1.502(4) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.394(5) . ? C5 H5A 0.9300 . ? C6 C7 1.368(7) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? 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 N3 Mn1 N3 155.84(15) 7 . ? N3 Mn1 N4 71.69(10) 7 7 ? N3 Mn1 N4 90.34(11) . 7 ? N3 Mn1 N4 90.34(11) 7 . ? N3 Mn1 N4 71.69(10) . . ? N4 Mn1 N4 85.17(17) 7 . ? N3 Mn1 S1 77.05(7) 7 7 ? N3 Mn1 S1 118.73(8) . 7 ? N4 Mn1 S1 148.65(8) 7 7 ? N4 Mn1 S1 92.78(9) . 7 ? N3 Mn1 S1 118.73(8) 7 . ? N3 Mn1 S1 77.05(7) . . ? N4 Mn1 S1 92.78(9) 7 . ? N4 Mn1 S1 148.65(8) . . ? S1 Mn1 S1 104.40(6) 7 . ? C1 S1 Mn1 96.65(13) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 N3 114.4(3) . . ? C2 N3 N2 116.8(3) . . ? C2 N3 Mn1 119.7(2) . . ? N2 N3 Mn1 123.6(2) . . ? C7 N4 C4 117.7(3) . . ? C7 N4 Mn1 127.5(3) . . ? C4 N4 Mn1 114.8(2) . . ? C5 N5 C6 117.4(4) . . ? N2 C1 N1 114.2(3) . . ? N2 C1 S1 128.3(3) . . ? N1 C1 S1 117.5(3) . . ? N3 C2 C4 116.5(3) . . ? N3 C2 C3 123.7(4) . . ? C4 C2 C3 119.8(3) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N4 C4 C5 118.5(4) . . ? N4 C4 C2 117.3(3) . . ? C5 C4 C2 124.2(3) . . ? N5 C5 C4 123.2(4) . . ? N5 C5 H5A 118.4 . . ? C4 C5 H5A 118.4 . . ? N5 C6 C7 121.3(4) . . ? N5 C6 H6A 119.4 . . ? C7 C6 H6A 119.4 . . ? N4 C7 C6 121.9(4) . . ? N4 C7 H7A 119.0 . . ? C6 C7 H7A 119.0 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.445 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.099 # Attachment 'compound1.cif' data_compound_1' _database_code_depnum_ccdc_archive 'CCDC 271336' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Mn N10 O0 S2' _chemical_formula_weight 443.43 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'P4(3)2(1)2 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 10.8908(17) _cell_length_b 10.8908(17) _cell_length_c 22.327(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2648.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5464 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 24.39 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.112 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 0.672 _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 293(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_reflns_number 12942 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2314 _reflns_number_gt 2144 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1250P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(4) _refine_ls_number_reflns 2314 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1569 _refine_ls_wR_factor_gt 0.1546 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 Mn1 Mn 0.17616(5) 0.17616(5) 0.0000 0.0413(3) Uani 1 2 d S . . S1 S 0.40097(9) 0.15140(11) 0.02170(5) 0.0565(3) Uani 1 1 d . . . C1 C 0.3853(4) 0.1068(4) 0.09583(18) 0.0496(9) Uani 1 1 d . . . N1 N 0.4889(3) 0.0853(4) 0.12710(18) 0.0658(11) Uani 1 1 d . . . H1A H 0.4846 0.0616 0.1638 0.079 Uiso 1 1 calc R . . H1B H 0.5593 0.0953 0.1104 0.079 Uiso 1 1 calc R . . N2 N 0.2822(3) 0.0884(4) 0.12621(14) 0.0515(8) Uani 1 1 d . . . C2 C 0.0743(4) 0.0914(4) 0.12241(16) 0.0473(9) Uani 1 1 d . . . N3 N 0.1777(3) 0.1113(3) 0.09477(13) 0.0429(7) Uani 1 1 d . . . C3 C 0.0656(5) 0.0490(6) 0.18705(19) 0.0780(16) Uani 1 1 d . . . H3A H 0.1447 0.0556 0.2057 0.117 Uiso 1 1 calc R . . H3B H 0.0388 -0.0350 0.1881 0.117 Uiso 1 1 calc R . . H3C H 0.0077 0.0995 0.2082 0.117 Uiso 1 1 calc R . . N4 N -0.0238(3) 0.1558(3) 0.03117(15) 0.0521(8) Uani 1 1 d . . . C4 C -0.0366(4) 0.1154(4) 0.08804(18) 0.0490(9) Uani 1 1 d . . . N5 N -0.2558(3) 0.1198(4) 0.0783(2) 0.0727(12) Uani 1 1 d . . . C5 C -0.1554(4) 0.0990(4) 0.1110(2) 0.0589(11) Uani 1 1 d . . . H5A H -0.1644 0.0727 0.1504 0.071 Uiso 1 1 calc R . . C6 C -0.2402(4) 0.1601(5) 0.0233(3) 0.0725(13) Uani 1 1 d . . . H6A H -0.3087 0.1755 -0.0004 0.087 Uiso 1 1 calc R . . C7 C -0.1257(4) 0.1798(4) 0.0002(2) 0.0669(12) Uani 1 1 d . . . H7A H -0.1186 0.2110 -0.0384 0.080 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 Mn1 0.0438(3) 0.0438(3) 0.0362(4) 0.0002(3) -0.0002(3) -0.0066(3) S1 0.0406(5) 0.0812(7) 0.0478(6) 0.0017(5) 0.0044(4) -0.0086(5) C1 0.044(2) 0.059(2) 0.045(2) -0.0059(19) 0.0018(17) -0.0003(17) N1 0.0393(19) 0.101(3) 0.057(2) 0.003(2) -0.0030(16) 0.0014(18) N2 0.0390(17) 0.073(2) 0.0429(17) 0.0027(18) -0.0022(14) 0.0023(15) C2 0.044(2) 0.054(2) 0.0442(18) 0.0086(18) 0.0059(17) 0.0006(16) N3 0.0392(16) 0.0499(17) 0.0397(15) 0.0045(14) 0.0024(13) 0.0005(13) C3 0.060(3) 0.114(4) 0.060(3) 0.035(3) 0.014(2) 0.010(3) N4 0.0417(17) 0.063(2) 0.0518(19) 0.0051(16) -0.0027(15) -0.0033(15) C4 0.044(2) 0.051(2) 0.052(2) 0.0002(19) 0.0091(18) -0.0027(17) N5 0.041(2) 0.081(3) 0.096(3) -0.011(3) 0.010(2) -0.0044(18) C5 0.037(2) 0.076(3) 0.064(3) 0.003(2) 0.0092(18) -0.0062(19) C6 0.046(2) 0.094(4) 0.077(3) 0.001(3) -0.008(2) 0.000(2) C7 0.052(2) 0.089(3) 0.059(2) 0.003(3) -0.007(2) 0.000(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 Mn1 N3 2.231(3) 7 ? Mn1 N3 2.231(3) . ? Mn1 N4 2.297(3) 7 ? Mn1 N4 2.297(3) . ? Mn1 S1 2.5103(11) . ? Mn1 S1 2.5104(11) 7 ? S1 C1 1.733(4) . ? C1 N2 1.327(5) . ? C1 N1 1.348(5) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 N3 1.361(4) . ? C2 N3 1.302(5) . ? C2 C4 1.455(6) . ? C2 C3 1.518(5) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? N4 C7 1.333(6) . ? N4 C4 1.351(5) . ? C4 C5 1.403(5) . ? N5 C6 1.315(7) . ? N5 C5 1.334(6) . ? C5 H5A 0.9300 . ? C6 C7 1.367(7) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? 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 N3 Mn1 N3 154.71(17) 7 . ? N3 Mn1 N4 71.88(11) 7 7 ? N3 Mn1 N4 89.30(12) . 7 ? N3 Mn1 N4 89.30(12) 7 . ? N3 Mn1 N4 71.88(11) . . ? N4 Mn1 N4 84.76(18) 7 . ? N3 Mn1 S1 119.53(9) 7 . ? N3 Mn1 S1 77.05(8) . . ? N4 Mn1 S1 92.91(10) 7 . ? N4 Mn1 S1 148.85(9) . . ? N3 Mn1 S1 77.05(8) 7 7 ? N3 Mn1 S1 119.53(9) . 7 ? N4 Mn1 S1 148.85(9) 7 7 ? N4 Mn1 S1 92.91(10) . 7 ? S1 Mn1 S1 104.29(6) . 7 ? C1 S1 Mn1 96.79(14) . . ? N2 C1 N1 114.7(4) . . ? N2 C1 S1 127.9(3) . . ? N1 C1 S1 117.4(3) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 N3 114.6(3) . . ? N3 C2 C4 116.0(3) . . ? N3 C2 C3 123.7(4) . . ? C4 C2 C3 120.3(4) . . ? C2 N3 N2 116.6(3) . . ? C2 N3 Mn1 119.7(3) . . ? N2 N3 Mn1 123.6(2) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C7 N4 C4 117.7(4) . . ? C7 N4 Mn1 127.8(3) . . ? C4 N4 Mn1 114.5(3) . . ? N4 C4 C5 118.7(4) . . ? N4 C4 C2 117.9(3) . . ? C5 C4 C2 123.4(4) . . ? C6 N5 C5 117.5(4) . . ? N5 C5 C4 122.3(4) . . ? N5 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? N5 C6 C7 121.5(5) . . ? N5 C6 H6A 119.3 . . ? C7 C6 H6A 119.3 . . ? N4 C7 C6 122.2(5) . . ? N4 C7 H7A 118.9 . . ? C6 C7 H7A 118.9 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.446 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.103 # Attachment 'compound 2.cif' data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 271337' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H21 B F4 N10 O2 S2 Zn' _chemical_formula_weight 577.71 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' Zn Zn 0.2839 1.4301 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 10.8203(10) _cell_length_b 10.8203(10) _cell_length_c 22.637(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2650.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1886 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 19.17 _exptl_crystal_description prism _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 1.143 _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 293(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_reflns_number 12837 _diffrn_reflns_av_R_equivalents 0.0864 _diffrn_reflns_av_sigmaI/netI 0.1541 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2318 _reflns_number_gt 1317 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.09(3) _refine_ls_number_reflns 2318 _refine_ls_number_parameters 219 _refine_ls_number_restraints 233 _refine_ls_R_factor_all 0.1182 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.1598 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.973 _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 Zn1 Zn 0.14862(6) 0.14862(6) 0.0000 0.0456(2) Uani 1 2 d S . . S1 S 0.37190(13) 0.13821(15) 0.01836(7) 0.0589(5) Uani 1 1 d . . . N1 N 0.4677(3) 0.0834(4) 0.1216(2) 0.0584(17) Uani 1 1 d . . . H1A H 0.4611 0.0719 0.1591 0.070 Uiso 1 1 calc R . . H1B H 0.5395 0.0847 0.1054 0.070 Uiso 1 1 calc R . . N2 N 0.2597(4) 0.0949(4) 0.1207(2) 0.0517(16) Uani 1 1 d . . . H2A H 0.2623 0.0841 0.1583 0.062 Uiso 0.50 1 calc PR . . N3 N 0.1466(4) 0.1078(3) 0.09260(16) 0.0364(12) Uani 1 1 d . . . N4 N -0.0461(4) 0.1329(5) 0.02641(19) 0.0517(15) Uani 1 1 d . . . N5 N -0.2838(4) 0.1186(5) 0.0713(3) 0.074(2) Uani 1 1 d . . . C1 C 0.3671(5) 0.0992(5) 0.0889(2) 0.0510(18) Uani 1 1 d . . . C2 C 0.0480(5) 0.0966(5) 0.1200(3) 0.0475(19) Uani 1 1 d . . . C3 C 0.0370(5) 0.0680(7) 0.1858(2) 0.073(2) Uani 1 1 d . . . H3A H -0.0284 0.1166 0.2026 0.110 Uiso 1 1 calc R . . H3B H 0.1135 0.0877 0.2051 0.110 Uiso 1 1 calc R . . H3C H 0.0191 -0.0182 0.1910 0.110 Uiso 1 1 calc R . . C4 C -0.0646(5) 0.1143(5) 0.0857(3) 0.0441(18) Uani 1 1 d . . . C5 C -0.1850(6) 0.1080(5) 0.1054(3) 0.072(2) Uani 1 1 d . . . H5B H -0.1978 0.0954 0.1456 0.087 Uiso 1 1 calc R . . C6 C -0.2618(6) 0.1371(6) 0.0159(3) 0.079(2) Uani 1 1 d . . . H6A H -0.3279 0.1472 -0.0099 0.095 Uiso 1 1 calc R . . C7 C -0.1404(5) 0.1424(6) -0.0065(2) 0.0697(19) Uani 1 1 d . . . H7A H -0.1291 0.1532 -0.0469 0.084 Uiso 1 1 calc R . . B1 B 0.3708(5) -0.2793(5) 0.1164(2) 0.104(2) Uani 0.50 1 d PDU . . F1 F 0.4099(10) -0.3453(8) 0.1630(3) 0.096(3) Uani 0.25 1 d PDU A 1 F2 F 0.4697(7) -0.2095(9) 0.0955(5) 0.107(3) Uani 0.25 1 d PDU A 1 F3 F 0.2828(8) -0.1939(8) 0.1320(5) 0.092(3) Uani 0.25 1 d PDU A 1 F4 F 0.3290(10) -0.3534(8) 0.0723(4) 0.093(3) Uani 0.25 1 d PDU A 1 F1' F 0.3591(16) -0.1626(7) 0.0979(6) 0.100(2) Uani 0.25 1 d PDU A 2 F2' F 0.4089(14) -0.2916(15) 0.0600(4) 0.108(2) Uani 0.25 1 d PDU A 2 F3' F 0.3775(15) -0.3197(12) 0.1730(4) 0.097(3) Uani 0.25 1 d PDU A 2 F4' F 0.2608(9) -0.3412(12) 0.1057(7) 0.107(3) Uani 0.25 1 d PDU A 2 O1W O 0.3265(5) 0.0013(6) 0.2323(2) 0.123(2) Uani 0.88 1 d P . . H1WA H 0.3846 0.0430 0.2479 0.147 Uiso 0.88 1 d PR . . H1WB H 0.3502 -0.0603 0.2208 0.147 Uiso 0.88 1 d PR . . O2W O 0.2307(15) -0.2307(15) 0.2500 0.076(7) Uiso 0.25 2 d SP . . 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 Zn1 0.0454(3) 0.0454(3) 0.0459(5) -0.0063(4) 0.0063(4) -0.0034(6) S1 0.0393(8) 0.0725(10) 0.0650(10) -0.0018(9) 0.0125(7) -0.0017(10) N1 0.012(2) 0.082(4) 0.081(4) 0.000(3) 0.000(2) 0.004(3) N2 0.044(3) 0.057(3) 0.054(3) -0.001(3) -0.013(3) 0.013(3) N3 0.034(2) 0.041(3) 0.034(2) -0.0033(18) 0.015(2) -0.003(2) N4 0.030(2) 0.075(4) 0.050(3) -0.001(3) 0.005(2) -0.002(3) N5 0.030(3) 0.091(5) 0.102(4) 0.002(4) -0.007(3) 0.002(3) C1 0.042(3) 0.042(3) 0.069(4) -0.013(3) 0.009(3) -0.013(3) C2 0.036(3) 0.046(4) 0.060(4) 0.010(3) 0.006(3) -0.007(3) C3 0.051(4) 0.123(6) 0.046(4) 0.013(4) 0.006(3) -0.006(4) C4 0.027(3) 0.040(4) 0.066(4) -0.001(3) 0.011(3) -0.010(3) C5 0.091(5) 0.055(4) 0.071(4) 0.002(3) 0.038(4) 0.008(4) C6 0.103(5) 0.091(5) 0.043(4) 0.013(4) -0.008(4) 0.029(5) C7 0.031(3) 0.118(5) 0.060(4) 0.004(5) -0.008(3) 0.004(4) B1 0.125(4) 0.079(4) 0.109(4) 0.003(4) -0.031(4) 0.011(4) F1 0.121(5) 0.063(5) 0.104(5) 0.000(5) -0.040(5) 0.019(5) F2 0.131(5) 0.078(5) 0.110(5) 0.001(5) -0.018(5) 0.006(5) F3 0.116(4) 0.069(4) 0.090(4) -0.002(4) -0.028(4) 0.016(4) F4 0.118(5) 0.062(4) 0.098(5) 0.016(5) -0.025(5) 0.020(5) F1' 0.120(4) 0.074(4) 0.106(4) 0.008(3) -0.029(4) 0.011(4) F2' 0.128(4) 0.085(4) 0.109(4) 0.005(4) -0.034(4) 0.013(4) F3' 0.122(5) 0.065(5) 0.105(5) 0.012(5) -0.042(5) 0.015(5) F4' 0.143(5) 0.069(5) 0.108(5) 0.024(5) -0.038(5) 0.022(5) O1W 0.084(4) 0.191(6) 0.093(4) 0.006(4) -0.032(4) -0.022(4) _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 Zn1 N3 2.142(4) 7 ? Zn1 N3 2.142(4) . ? Zn1 N4 2.197(4) 7 ? Zn1 N4 2.197(4) . ? Zn1 S1 2.4541(15) . ? Zn1 S1 2.4541(15) 7 ? S1 C1 1.653(6) . ? N1 C1 1.327(7) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 C1 1.368(7) . ? N2 N3 1.386(6) . ? N2 H2A 0.8600 . ? N3 C2 1.240(6) . ? N4 C7 1.268(6) . ? N4 C4 1.372(7) . ? N5 C6 1.292(8) . ? N5 C5 1.324(8) . ? C2 C4 1.457(8) . ? C2 C3 1.527(8) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.379(8) . ? C5 H5B 0.9300 . ? C6 C7 1.409(8) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? B1 F1' 1.336(8) . ? B1 F1 1.343(7) . ? B1 F2' 1.348(8) . ? B1 F4 1.356(7) . ? B1 F3' 1.357(8) . ? B1 F3 1.373(7) . ? B1 F4' 1.386(8) . ? B1 F2 1.393(7) . ? F1' F2' 1.725(18) . ? O1W H1WA 0.8500 . ? O1W H1WB 0.7603 . ? 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 N3 Zn1 N3 162.4(2) 7 . ? N3 Zn1 N4 73.03(16) 7 7 ? N3 Zn1 N4 93.90(15) . 7 ? N3 Zn1 N4 93.90(15) 7 . ? N3 Zn1 N4 73.03(16) . . ? N4 Zn1 N4 85.7(3) 7 . ? N3 Zn1 S1 111.59(10) 7 . ? N3 Zn1 S1 80.49(11) . . ? N4 Zn1 S1 94.49(14) 7 . ? N4 Zn1 S1 153.46(12) . . ? N3 Zn1 S1 80.49(11) 7 7 ? N3 Zn1 S1 111.59(10) . 7 ? N4 Zn1 S1 153.46(12) 7 7 ? N4 Zn1 S1 94.49(14) . 7 ? S1 Zn1 S1 96.84(8) . 7 ? C1 S1 Zn1 98.3(2) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 N3 120.4(4) . . ? C1 N2 H2A 119.8 . . ? N3 N2 H2A 119.8 . . ? C2 N3 N2 121.4(4) . . ? C2 N3 Zn1 121.2(4) . . ? N2 N3 Zn1 117.4(3) . . ? C7 N4 C4 118.0(5) . . ? C7 N4 Zn1 127.3(4) . . ? C4 N4 Zn1 114.7(3) . . ? C6 N5 C5 115.6(6) . . ? N1 C1 N2 113.6(5) . . ? N1 C1 S1 123.1(4) . . ? N2 C1 S1 122.9(4) . . ? N3 C2 C4 116.2(5) . . ? N3 C2 C3 125.1(5) . . ? C4 C2 C3 118.8(5) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N4 C4 C5 117.5(5) . . ? N4 C4 C2 114.7(5) . . ? C5 C4 C2 127.7(6) . . ? N5 C5 C4 124.7(6) . . ? N5 C5 H5B 117.6 . . ? C4 C5 H5B 117.6 . . ? N5 C6 C7 121.8(6) . . ? N5 C6 H6A 119.1 . . ? C7 C6 H6A 119.1 . . ? N4 C7 C6 122.4(5) . . ? N4 C7 H7A 118.8 . . ? C6 C7 H7A 118.8 . . ? F1' B1 F1 141.1(8) . . ? F1' B1 F2' 80.0(9) . . ? F1 B1 F2' 126.6(9) . . ? F1' B1 F4 107.3(8) . . ? F1 B1 F4 111.7(6) . . ? F2' B1 F4 49.3(8) . . ? F1' B1 F3' 127.2(9) . . ? F1 B1 F3' 21.3(8) . . ? F2' B1 F3' 147.9(10) . . ? F4 B1 F3' 121.5(8) . . ? F1' B1 F3 51.6(8) . . ? F1 B1 F3 111.9(7) . . ? F2' B1 F3 121.5(9) . . ? F4 B1 F3 110.9(7) . . ? F3' B1 F3 90.6(9) . . ? F1' B1 F4' 108.7(10) . . ? F1 B1 F4' 98.7(8) . . ? F2' B1 F4' 92.9(10) . . ? F4 B1 F4' 45.7(8) . . ? F3' B1 F4' 93.2(10) . . ? F3 B1 F4' 77.0(8) . . ? F1' B1 F2 56.9(8) . . ? F1 B1 F2 108.3(7) . . ? F2' B1 F2 59.8(8) . . ? F4 B1 F2 109.0(6) . . ? F3' B1 F2 117.0(9) . . ? F3 B1 F2 104.8(6) . . ? F4' B1 F2 149.6(9) . . ? B1 F1' F2' 50.3(5) . . ? B1 F2' F1' 49.7(6) . . ? H1WA O1W H1WB 110.9 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.439 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.083 # Attachment 'compound 3.txt' data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 271338' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 N10 O0.50 S2 Zn' _chemical_formula_weight 476.89 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' 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 10.840(2) _cell_length_b 10.840(2) _cell_length_c 22.079(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2594.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2916 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 20.52 _exptl_crystal_description prism _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 1.129 _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 293(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_reflns_number 12827 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2282 _reflns_number_gt 2142 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0950P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.007(18) _refine_ls_number_reflns 2282 _refine_ls_number_parameters 140 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1183 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.054 _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 Zn1 Zn 0.66781(3) 0.66781(3) 0.0000 0.0393(2) Uani 1 2 d S . . S1 S 0.88692(9) 0.64498(9) 0.01639(4) 0.0491(3) Uani 1 1 d . . . N1 N 0.9773(3) 0.5928(4) 0.12377(14) 0.0606(9) Uani 1 1 d . . . H1A H 0.9743 0.5746 0.1617 0.073 Uiso 1 1 calc R . . H1B H 1.0475 0.6010 0.1061 0.073 Uiso 1 1 calc R . . N2 N 0.7698(3) 0.5937(3) 0.12397(13) 0.0439(7) Uani 1 1 d . . . N3 N 0.6644(3) 0.6141(3) 0.09212(12) 0.0387(6) Uani 1 1 d . . . N4 N 0.4650(3) 0.6497(3) 0.02559(13) 0.0472(7) Uani 1 1 d . . . N5 N 0.2310(3) 0.6211(4) 0.07346(18) 0.0625(9) Uani 1 1 d . . . C1 C 0.8725(3) 0.6084(3) 0.09228(16) 0.0425(8) Uani 1 1 d . . . C2 C 0.5606(3) 0.5946(3) 0.11980(15) 0.0429(8) Uani 1 1 d . . . C3 C 0.5513(5) 0.5558(5) 0.18374(17) 0.0691(12) Uani 1 1 d . . . H3A H 0.6276 0.5730 0.2041 0.104 Uiso 1 1 calc R . . H3B H 0.5346 0.4689 0.1856 0.104 Uiso 1 1 calc R . . H3C H 0.4856 0.6002 0.2031 0.104 Uiso 1 1 calc R . . C4 C 0.4496(3) 0.6154(3) 0.08436(16) 0.0431(8) Uani 1 1 d . . . C5 C 0.3317(4) 0.6022(4) 0.10722(19) 0.0562(9) Uani 1 1 d . . . H5A H 0.3221 0.5795 0.1475 0.067 Uiso 1 1 calc R . . C6 C 0.2471(4) 0.6552(5) 0.0167(2) 0.0684(12) Uani 1 1 d . . . H6A H 0.1787 0.6694 -0.0077 0.082 Uiso 1 1 calc R . . C7 C 0.3657(4) 0.6705(4) -0.0072(2) 0.0615(10) Uani 1 1 d . . . H7A H 0.3746 0.6960 -0.0472 0.074 Uiso 1 1 calc R . . O1 O 0.587(3) 0.143(3) 0.2371(11) 0.104(10) Uiso 0.13 1 d PDU A 1 H1C H 0.5291 0.1510 0.2606 0.157 Uiso 0.13 1 calc PR A 1 O1' O 0.458(3) 0.245(4) 0.1433(15) 0.119(12) Uiso 0.13 1 d PDU A 2 H1'A H 0.3964 0.2560 0.1642 0.179 Uiso 0.13 1 calc PR A 2 C9 C 0.669(3) 0.193(3) 0.1433(12) 0.141(12) Uiso 0.25 1 d PDU A . H9D H 0.7368 0.1700 0.1686 0.212 Uiso 0.13 1 d PR B 2 H9E H 0.6521 0.1286 0.1147 0.212 Uiso 0.13 1 d PR B 2 H9F H 0.6883 0.2678 0.1220 0.212 Uiso 0.13 1 d PR B 2 H9A H 0.6575 0.2332 0.1049 0.212 Uiso 0.13 1 d PR B 1 H9B H 0.7397 0.2268 0.1633 0.212 Uiso 0.13 1 d PR B 1 H9C H 0.6800 0.1063 0.1371 0.212 Uiso 0.13 1 d PR B 1 C8 C 0.560(3) 0.207(4) 0.1818(10) 0.143(11) Uiso 0.25 1 d PDU . . H8A H 0.5395 0.1335 0.2034 0.172 Uiso 0.13 1 d PR A 2 H8D H 0.5754 0.2719 0.2106 0.172 Uiso 0.13 1 d PR A 2 H8C H 0.5474 0.2939 0.1889 0.172 Uiso 0.13 1 d PR A 1 H8B H 0.4879 0.1739 0.1628 0.172 Uiso 0.13 1 d PR A 1 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 Zn1 0.0416(2) 0.0416(2) 0.0347(3) 0.00073(17) -0.00073(17) -0.0048(2) S1 0.0373(5) 0.0687(6) 0.0415(5) 0.0014(4) 0.0046(4) -0.0045(4) N1 0.0384(18) 0.094(3) 0.0495(17) -0.0037(18) -0.0028(15) 0.0032(17) N2 0.0337(15) 0.0570(18) 0.0410(14) 0.0027(14) 0.0004(13) 0.0023(14) N3 0.0362(14) 0.0437(15) 0.0361(13) -0.0014(12) 0.0019(12) 0.0004(12) N4 0.0371(16) 0.0550(19) 0.0494(16) 0.0022(14) 0.0021(13) -0.0017(13) N5 0.0346(17) 0.075(2) 0.078(2) -0.004(2) 0.0049(17) -0.0050(16) C1 0.0367(18) 0.0455(19) 0.0453(18) -0.0021(16) -0.0013(14) 0.0018(14) C2 0.0369(18) 0.051(2) 0.0405(16) 0.0053(16) 0.0054(15) -0.0017(15) C3 0.058(3) 0.094(4) 0.055(2) 0.029(2) 0.012(2) 0.005(2) C4 0.0363(18) 0.0439(19) 0.0491(18) -0.0016(16) 0.0048(15) -0.0014(14) C5 0.040(2) 0.065(2) 0.064(2) 0.000(2) 0.0157(19) -0.0075(18) C6 0.037(2) 0.087(3) 0.082(3) 0.000(3) -0.0092(19) 0.0013(19) C7 0.046(2) 0.083(3) 0.056(2) 0.008(2) -0.0039(17) -0.0004(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 Zn1 N3 2.116(3) 7 ? Zn1 N3 2.116(3) . ? Zn1 N4 2.278(3) 7 ? Zn1 N4 2.278(3) . ? Zn1 S1 2.4153(11) . ? Zn1 S1 2.4153(11) 7 ? S1 C1 1.729(4) . ? N1 C1 1.343(5) . ? N2 C1 1.324(5) . ? N2 N3 1.360(4) . ? N3 C2 1.298(4) . ? N4 C7 1.317(5) . ? N4 C4 1.360(4) . ? N5 C6 1.317(6) . ? N5 C5 1.338(5) . ? C2 C4 1.453(5) . ? C2 C3 1.477(5) . ? C4 C5 1.381(5) . ? C6 C7 1.400(6) . ? O1 C8 1.436(10) . ? O1' C8 1.453(10) . ? C9 C8 1.457(10) . ? 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 N3 Zn1 N3 156.14(16) 7 . ? N3 Zn1 N4 73.81(11) 7 7 ? N3 Zn1 N4 88.37(11) . 7 ? N3 Zn1 N4 88.37(11) 7 . ? N3 Zn1 N4 73.81(11) . . ? N4 Zn1 N4 83.99(16) 7 . ? N3 Zn1 S1 114.38(8) 7 . ? N3 Zn1 S1 81.07(8) . . ? N4 Zn1 S1 91.32(9) 7 . ? N4 Zn1 S1 154.54(8) . . ? N3 Zn1 S1 81.07(8) 7 7 ? N3 Zn1 S1 114.38(8) . 7 ? N4 Zn1 S1 154.54(8) 7 7 ? N4 Zn1 S1 91.32(9) . 7 ? S1 Zn1 S1 102.94(5) . 7 ? C1 S1 Zn1 94.56(12) . . ? C1 N2 N3 114.4(3) . . ? C2 N3 N2 117.3(3) . . ? C2 N3 Zn1 120.8(2) . . ? N2 N3 Zn1 121.8(2) . . ? C7 N4 C4 118.1(3) . . ? C7 N4 Zn1 129.6(3) . . ? C4 N4 Zn1 112.3(2) . . ? C6 N5 C5 117.6(4) . . ? N2 C1 N1 115.0(3) . . ? N2 C1 S1 128.0(3) . . ? N1 C1 S1 117.0(3) . . ? N3 C2 C4 116.1(3) . . ? N3 C2 C3 123.8(3) . . ? C4 C2 C3 120.1(3) . . ? N4 C4 C5 119.4(3) . . ? N4 C4 C2 117.0(3) . . ? C5 C4 C2 123.6(3) . . ? N5 C5 C4 122.4(4) . . ? N5 C6 C7 120.9(4) . . ? N4 C7 C6 121.6(4) . . ? O1 C8 O1' 142(3) . . ? O1 C8 C9 106.3(14) . . ? O1' C8 C9 107.7(14) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.746 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.135 # Attachment 'compound 4.cif' data_compound_4 _database_code_depnum_ccdc_archive 'CCDC 271339' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H22 Cl2 N10 Ni O10 S2' _chemical_formula_weight 684.15 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' Ni Ni 0.3393 1.1124 '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 Tetragonal _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 10.8780(11) _cell_length_b 10.8780(11) _cell_length_c 22.466(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2658.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1542 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 24.34 _exptl_crystal_description block _exptl_crystal_colour dark-brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 1.156 _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 293(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_reflns_number 13314 _diffrn_reflns_av_R_equivalents 0.0725 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2335 _reflns_number_gt 1894 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0880P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(5) _refine_ls_number_reflns 2335 _refine_ls_number_parameters 208 _refine_ls_number_restraints 92 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0616 _refine_ls_wR_factor_ref 0.1581 _refine_ls_wR_factor_gt 0.1499 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.099 _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 Ni1 Ni 0.12838(5) 0.12838(5) 0.0000 0.02766(18) Uani 1 2 d S . . S1 S 0.34946(10) 0.12237(12) 0.01063(5) 0.0389(3) Uani 1 1 d . . . N1 N 0.4507(4) 0.0861(4) 0.1162(2) 0.0492(14) Uani 1 1 d . . . H1A H 0.4461 0.0780 0.1542 0.059 Uiso 1 1 calc R . . H1B H 0.5213 0.0859 0.0989 0.059 Uiso 1 1 calc R . . N2 N 0.2454(3) 0.0973(4) 0.11758(18) 0.0359(11) Uani 1 1 d . . . H2A H 0.2486 0.0900 0.1557 0.043 Uiso 1 1 calc RD . . N3 N 0.1355(3) 0.1077(3) 0.08920(15) 0.0273(9) Uani 1 1 d . . . N4 N -0.0573(3) 0.1207(4) 0.02383(17) 0.0348(11) Uani 1 1 d . . . N5 N -0.2927(4) 0.1091(4) 0.0694(2) 0.0463(13) Uani 1 1 d . . . C1 C 0.3499(4) 0.0987(4) 0.0845(2) 0.0336(12) Uani 1 1 d . . . C2 C 0.0345(4) 0.1065(4) 0.1194(2) 0.0275(12) Uani 1 1 d . . . C3 C 0.0281(5) 0.0940(5) 0.1855(2) 0.0484(16) Uani 1 1 d . . . H3A H 0.0568 0.1685 0.2037 0.073 Uiso 1 1 calc R . . H3B H 0.0789 0.0266 0.1980 0.073 Uiso 1 1 calc RD . . H3C H -0.0554 0.0790 0.1972 0.073 Uiso 1 1 calc R . . C4 C -0.0755(4) 0.1131(4) 0.0830(2) 0.0286(12) Uani 1 1 d . . . C5 C -0.1951(4) 0.1093(5) 0.1045(2) 0.0397(14) Uani 1 1 d . . . H5A H -0.2071 0.1066 0.1455 0.048 Uiso 1 1 calc R . . C6 C -0.2720(5) 0.1134(5) 0.0119(3) 0.0529(17) Uani 1 1 d . . . H6A H -0.3384 0.1121 -0.0142 0.064 Uiso 1 1 calc R . . C7 C -0.1550(4) 0.1199(4) -0.0109(2) 0.0396(13) Uani 1 1 d . . . H7A H -0.1444 0.1239 -0.0519 0.048 Uiso 1 1 calc R . . Cl1 Cl -0.1396(2) -0.21720(18) 0.13124(9) 0.1072(8) Uani 1 1 d DU . . O11 O -0.1395(7) -0.1735(6) 0.0725(2) 0.161(3) Uani 1 1 d DU A . O12 O -0.2335(7) -0.1418(8) 0.1591(4) 0.142(4) Uani 0.543(6) 1 d PDU A 1 O13 O -0.1519(9) -0.3364(5) 0.1506(5) 0.117(3) Uani 0.543(6) 1 d PDU A 1 O14 O -0.0172(6) -0.1729(10) 0.1468(5) 0.145(4) Uani 0.543(6) 1 d PDU A 1 O12' O -0.2170(8) -0.3240(7) 0.1304(6) 0.124(4) Uani 0.457(6) 1 d PDU A 2 O13' O -0.1653(11) -0.1366(8) 0.1784(4) 0.112(3) Uani 0.457(6) 1 d PDU A 2 O14' O -0.0177(7) -0.2737(11) 0.1397(6) 0.148(4) Uani 0.457(6) 1 d PDU A 2 O1W O 0.3224(5) 0.0109(6) 0.2272(2) 0.071(2) Uani 0.75 1 d P . . H1WA H 0.2948 0.0712 0.2459 0.085 Uiso 0.75 1 d PR . . H1WB H 0.3113 -0.0629 0.2364 0.085 Uiso 0.75 1 d PR . . O2W O 0.1954(10) -0.1954(10) 0.2500 0.099(5) Uiso 0.50 2 d SP . . 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 Ni1 0.0276(2) 0.0276(2) 0.0277(4) -0.0024(3) 0.0024(3) -0.0010(4) S1 0.0296(6) 0.0489(7) 0.0383(6) -0.0025(6) 0.0078(5) -0.0016(6) N1 0.029(2) 0.069(3) 0.050(3) 0.001(3) 0.000(2) -0.003(2) N2 0.031(2) 0.047(3) 0.029(2) -0.0023(19) -0.0038(19) -0.001(2) N3 0.0274(18) 0.030(2) 0.0247(17) 0.0006(15) 0.0009(17) -0.0064(17) N4 0.0261(19) 0.043(2) 0.035(2) -0.007(2) -0.0006(16) -0.0004(19) N5 0.030(2) 0.060(3) 0.049(3) 0.011(2) 0.007(2) 0.002(2) C1 0.026(2) 0.030(3) 0.045(3) -0.002(2) 0.002(2) -0.002(2) C2 0.032(2) 0.020(2) 0.031(2) -0.001(2) 0.003(2) -0.0004(19) C3 0.042(3) 0.073(4) 0.031(3) 0.002(3) 0.002(2) 0.005(3) C4 0.034(2) 0.022(2) 0.030(2) -0.005(2) 0.0078(19) -0.006(2) C5 0.030(2) 0.046(3) 0.043(3) -0.005(3) 0.008(2) -0.003(2) C6 0.038(3) 0.055(3) 0.065(4) 0.002(3) -0.008(3) 0.002(3) C7 0.029(2) 0.047(3) 0.043(3) 0.001(3) -0.004(2) -0.002(2) Cl1 0.1476(18) 0.0849(14) 0.0892(13) 0.0096(11) 0.0324(15) -0.0283(14) O11 0.221(7) 0.147(5) 0.116(5) 0.022(4) 0.056(5) -0.002(5) O12 0.175(8) 0.107(7) 0.144(7) 0.009(6) 0.092(6) -0.014(7) O13 0.135(7) 0.052(5) 0.164(7) 0.021(5) 0.040(6) -0.005(5) O14 0.167(7) 0.118(7) 0.151(7) -0.022(6) 0.023(7) -0.068(6) O12' 0.134(8) 0.083(7) 0.156(9) 0.004(7) 0.047(8) -0.025(7) O13' 0.143(7) 0.108(6) 0.087(6) -0.035(6) 0.044(6) -0.035(6) O14' 0.166(8) 0.118(8) 0.160(8) -0.004(7) 0.012(8) -0.005(7) O1W 0.050(3) 0.133(5) 0.030(3) 0.024(3) -0.011(2) -0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N3 2.018(3) 7 ? Ni1 N3 2.018(3) . ? Ni1 N4 2.091(4) 7 ? Ni1 N4 2.091(4) . ? Ni1 S1 2.4176(12) 7 ? Ni1 S1 2.4176(12) . ? S1 C1 1.680(5) . ? N1 C1 1.315(6) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 C1 1.358(6) . ? N2 N3 1.359(5) . ? N2 H2A 0.8600 . ? N3 C2 1.291(5) . ? N4 C7 1.318(6) . ? N4 C4 1.346(6) . ? N5 C6 1.314(7) . ? N5 C5 1.322(6) . ? C2 C4 1.450(6) . ? C2 C3 1.493(7) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.389(6) . ? C5 H5A 0.9300 . ? C6 C7 1.373(7) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? Cl1 O13 1.374(6) . ? Cl1 O13' 1.403(7) . ? Cl1 O11 1.404(5) . ? Cl1 O12' 1.435(7) . ? Cl1 O12 1.451(7) . ? Cl1 O14 1.459(7) . ? Cl1 O14' 1.475(7) . ? O1W H1WA 0.8353 . ? O1W H1WB 0.8377 . ? 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 N3 Ni1 N3 174.10(19) 7 . ? N3 Ni1 N4 77.21(14) 7 7 ? N3 Ni1 N4 98.52(14) . 7 ? N3 Ni1 N4 98.52(14) 7 . ? N3 Ni1 N4 77.21(14) . . ? N4 Ni1 N4 89.3(2) 7 . ? N3 Ni1 S1 81.98(10) 7 7 ? N3 Ni1 S1 102.12(10) . 7 ? N4 Ni1 S1 159.13(11) 7 7 ? N4 Ni1 S1 92.24(12) . 7 ? N3 Ni1 S1 102.12(10) 7 . ? N3 Ni1 S1 81.98(10) . . ? N4 Ni1 S1 92.24(12) 7 . ? N4 Ni1 S1 159.13(11) . . ? S1 Ni1 S1 93.64(7) 7 . ? C1 S1 Ni1 96.00(16) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 N3 118.6(4) . . ? C1 N2 H2A 120.7 . . ? N3 N2 H2A 120.7 . . ? C2 N3 N2 120.1(4) . . ? C2 N3 Ni1 119.3(3) . . ? N2 N3 Ni1 120.6(3) . . ? C7 N4 C4 117.7(4) . . ? C7 N4 Ni1 128.9(3) . . ? C4 N4 Ni1 113.4(3) . . ? C6 N5 C5 116.7(4) . . ? N1 C1 N2 113.6(4) . . ? N1 C1 S1 123.6(4) . . ? N2 C1 S1 122.7(4) . . ? N3 C2 C4 114.0(4) . . ? N3 C2 C3 124.2(4) . . ? C4 C2 C3 121.8(4) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N4 C4 C5 118.9(4) . . ? N4 C4 C2 116.0(4) . . ? C5 C4 C2 125.1(4) . . ? N5 C5 C4 123.0(5) . . ? N5 C5 H5A 118.5 . . ? C4 C5 H5A 118.5 . . ? N5 C6 C7 121.8(5) . . ? N5 C6 H6A 119.1 . . ? C7 C6 H6A 119.1 . . ? N4 C7 C6 121.8(5) . . ? N4 C7 H7A 119.1 . . ? C6 C7 H7A 119.1 . . ? O13 Cl1 O13' 109.4(6) . . ? O13 Cl1 O11 128.1(5) . . ? O13' Cl1 O11 120.0(5) . . ? O13 Cl1 O12' 35.2(6) . . ? O13' Cl1 O12' 113.5(6) . . ? O11 Cl1 O12' 105.2(6) . . ? O13 Cl1 O12 109.2(6) . . ? O13' Cl1 O12 35.1(6) . . ? O11 Cl1 O12 102.4(5) . . ? O12' Cl1 O12 92.9(6) . . ? O13 Cl1 O14 109.0(6) . . ? O13' Cl1 O14 78.1(6) . . ? O11 Cl1 O14 96.4(5) . . ? O12' Cl1 O14 143.8(6) . . ? O12 Cl1 O14 110.6(6) . . ? O13 Cl1 O14' 69.7(6) . . ? O13' Cl1 O14' 110.0(7) . . ? O11 Cl1 O14' 105.1(6) . . ? O12' Cl1 O14' 101.1(6) . . ? O12 Cl1 O14' 144.4(7) . . ? O14 Cl1 O14' 44.4(6) . . ? H1WA O1W H1WB 125.2 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.549 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.102 # Attachment 'compound 5.txt' data_compound_5 _database_code_depnum_ccdc_archive 'CCDC 271340' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H22 Cd Cl2 N10 O10 S2' _chemical_formula_weight 737.84 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.803(2) _cell_length_b 10.815(2) _cell_length_c 23.309(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2723.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 916 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 20.87 _exptl_crystal_description block _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.800 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 1.219 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6293 _exptl_absorpt_correction_T_max 0.7678 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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_reflns_number 13375 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4778 _reflns_number_gt 4300 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.08(5) _refine_ls_number_reflns 4778 _refine_ls_number_parameters 395 _refine_ls_number_restraints 223 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1247 _refine_ls_wR_factor_gt 0.1212 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.001 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 Cd1 Cd 0.60364(3) 0.30590(3) 0.142021(14) 0.03454(8) Uani 1 1 d . . . S1 S 0.37804(11) 0.30715(14) 0.10667(5) 0.0452(3) Uani 1 1 d . . . S2 S 0.62789(14) 0.07890(12) 0.17148(5) 0.0467(4) Uani 1 1 d . . . N1 N 0.2931(4) 0.4179(4) 0.01451(19) 0.0511(13) Uani 1 1 d . . . H1A H 0.3004 0.4562 -0.0176 0.061 Uiso 1 1 calc R . . H1B H 0.2208 0.4007 0.0277 0.061 Uiso 1 1 calc R . . N2 N 0.5015(4) 0.4162(4) 0.01966(17) 0.0433(12) Uani 1 1 d . . . H2A H 0.5032 0.4552 -0.0125 0.052 Uiso 1 1 calc RD . . N3 N 0.6096(4) 0.3859(4) 0.04598(16) 0.0381(10) Uani 1 1 d . . . N4 N 0.8053(4) 0.3227(4) 0.10561(17) 0.0401(11) Uani 1 1 d . . . N5 N 1.0405(4) 0.3464(4) 0.0605(2) 0.0524(14) Uani 1 1 d . . . N6 N 0.6699(4) -0.0019(4) 0.27433(17) 0.0456(12) Uani 1 1 d . . . H6B H 0.6825 0.0061 0.3106 0.055 Uiso 1 1 calc R . . H6C H 0.6669 -0.0744 0.2592 0.055 Uiso 1 1 calc R . . N7 N 0.6616(4) 0.2047(4) 0.27041(16) 0.0411(11) Uani 1 1 d . . . H7B H 0.6733 0.2064 0.3069 0.049 Uiso 1 1 calc RD . . N8 N 0.6496(4) 0.3122(4) 0.24119(16) 0.0371(10) Uani 1 1 d . . . N9 N 0.6234(4) 0.5123(4) 0.17708(16) 0.0401(11) Uani 1 1 d . . . N10 N 0.6531(5) 0.7464(4) 0.2253(2) 0.0496(13) Uani 1 1 d . . . C1 C 0.3918(5) 0.3858(4) 0.04330(19) 0.0391(12) Uani 1 1 d . . . C2 C 0.7130(4) 0.4128(4) 0.02096(19) 0.0340(12) Uani 1 1 d . . . C3 C 0.7258(5) 0.4733(6) -0.0352(2) 0.0542(17) Uani 1 1 d . . . H3A H 0.6578 0.4500 -0.0594 0.081 Uiso 1 1 calc RD . . H3B H 0.8022 0.4481 -0.0527 0.081 Uiso 1 1 calc R . . H3C H 0.7259 0.5614 -0.0302 0.081 Uiso 1 1 calc R . . C4 C 0.8230(5) 0.3699(5) 0.0546(2) 0.0412(14) Uani 1 1 d . . . C5 C 0.9418(5) 0.3817(5) 0.0324(2) 0.0429(14) Uani 1 1 d . . . H5A H 0.9516 0.4161 -0.0038 0.052 Uiso 1 1 calc R . . C6 C 1.0239(5) 0.3035(7) 0.1127(3) 0.0621(17) Uani 1 1 d . . . H6A H 1.0918 0.2829 0.1353 0.074 Uiso 1 1 calc R . . C7 C 0.9045(5) 0.2891(5) 0.1340(2) 0.0554(15) Uani 1 1 d . . . H7A H 0.8946 0.2540 0.1702 0.066 Uiso 1 1 calc R . . C8 C 0.6554(5) 0.0943(5) 0.2428(2) 0.0377(13) Uani 1 1 d . . . C9 C 0.6614(5) 0.4150(5) 0.2686(2) 0.0398(13) Uani 1 1 d . . . C10 C 0.6912(7) 0.4255(5) 0.3302(2) 0.0639(19) Uani 1 1 d . . . H10A H 0.6479 0.3625 0.3511 0.096 Uiso 1 1 calc RD . . H10B H 0.6664 0.5054 0.3439 0.096 Uiso 1 1 calc R . . H10C H 0.7788 0.4154 0.3356 0.096 Uiso 1 1 calc R . . C11 C 0.6468(4) 0.5259(4) 0.2328(2) 0.0337(12) Uani 1 1 d . . . C12 C 0.6627(5) 0.6459(4) 0.2564(2) 0.0425(14) Uani 1 1 d . . . H12A H 0.6804 0.6534 0.2953 0.051 Uiso 1 1 calc R . . C13 C 0.6309(6) 0.7299(5) 0.1698(3) 0.0558(18) Uani 1 1 d . . . H13A H 0.6250 0.7985 0.1459 0.067 Uiso 1 1 calc R . . C14 C 0.6163(6) 0.6121(5) 0.1466(2) 0.0573(16) Uani 1 1 d . . . H14A H 0.6008 0.6049 0.1075 0.069 Uiso 1 1 calc R . . Cl1 Cl 0.06015(18) 0.68880(17) -0.01324(7) 0.0856(6) Uani 1 1 d DU . . O11 O -0.0094(7) 0.7968(6) -0.0246(3) 0.111(3) Uiso 0.65 1 d PDU A 1 O12 O 0.0313(8) 0.5962(6) -0.0534(3) 0.100(2) Uiso 0.65 1 d PDU A 1 O13 O 0.0638(8) 0.6466(7) 0.0434(2) 0.103(3) Uiso 0.65 1 d PDU A 1 O14 O 0.1880(6) 0.7256(9) -0.0261(4) 0.136(3) Uiso 0.65 1 d PDU A 1 O11' O -0.0361(8) 0.7403(11) -0.0491(4) 0.105(4) Uiso 0.35 1 d PDU A 2 O12' O 0.1562(8) 0.7724(10) -0.0053(7) 0.145(5) Uiso 0.35 1 d PDU A 2 O13' O -0.0073(10) 0.6631(12) 0.0389(3) 0.094(4) Uiso 0.35 1 d PDU A 2 O14' O 0.0944(10) 0.5794(7) -0.0438(4) 0.072(3) Uiso 0.35 1 d PDU A 2 Cl2' Cl 0.9878(4) 0.6314(5) 0.1959(2) 0.1614(19) Uani 0.50 1 d PDU B 2 O21' O 0.8860(7) 0.6248(14) 0.1588(4) 0.178(4) Uani 0.50 1 d PDU B 2 O23' O 0.9484(10) 0.6573(14) 0.2527(3) 0.188(4) Uani 0.50 1 d PDU B 2 O22' O 1.0689(9) 0.5297(8) 0.1894(7) 0.197(4) Uani 0.50 1 d PDU B 2 O24' O 1.0563(10) 0.7390(9) 0.1770(6) 0.212(5) Uani 0.50 1 d PDU B 2 Cl2 Cl 0.9980(5) 0.5548(6) 0.2470(2) 0.1742(19) Uani 0.50 1 d PDU C 1 O21 O 1.0838(8) 0.6510(8) 0.2338(6) 0.176(3) Uani 0.50 1 d PDU C 1 O22 O 0.9186(9) 0.5306(14) 0.2006(4) 0.181(3) Uani 0.50 1 d PDU C 1 O23 O 0.9299(10) 0.5891(14) 0.2971(4) 0.211(5) Uani 0.50 1 d PDU C 1 O24 O 1.0693(10) 0.4489(9) 0.2645(7) 0.230(5) Uani 0.50 1 d PDU C 1 O1W O 0.7137(6) 0.1432(5) 0.3869(2) 0.099(2) Uani 1 1 d . . . H1WB H 0.7881 0.1607 0.3956 0.119 Uiso 1 1 d R . . H1WA H 0.6641 0.1787 0.4100 0.119 Uiso 1 1 d R . . O2W O 0.4182(6) 0.5480(6) -0.0771(2) 0.127(2) Uani 1 1 d . . . H2WA H 0.4140 0.6169 -0.0596 0.153 Uiso 1 1 d R . . H2WB H 0.4023 0.5770 -0.1102 0.153 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.03777(16) 0.03339(15) 0.03246(14) 0.00050(16) 0.00051(16) -0.00268(18) S1 0.0386(7) 0.0529(7) 0.0441(6) 0.0018(6) 0.0002(6) -0.0082(8) S2 0.0661(10) 0.0332(6) 0.0406(6) -0.0035(5) -0.0016(7) 0.0011(7) N1 0.027(2) 0.074(3) 0.052(2) 0.012(3) -0.0077(19) 0.005(2) N2 0.044(2) 0.047(2) 0.039(2) 0.008(2) -0.004(2) -0.002(2) N3 0.033(2) 0.042(2) 0.040(2) 0.0011(17) -0.001(2) -0.006(2) N4 0.034(2) 0.046(2) 0.040(2) 0.005(2) -0.0033(18) -0.007(2) N5 0.035(2) 0.054(3) 0.068(3) -0.003(2) 0.001(2) -0.003(2) N6 0.076(3) 0.023(2) 0.037(2) 0.0042(17) -0.009(2) -0.005(2) N7 0.061(2) 0.028(2) 0.035(2) -0.0040(19) 0.0003(19) -0.001(2) N8 0.042(2) 0.0256(19) 0.044(2) 0.0052(19) -0.0016(18) 0.002(2) N9 0.043(2) 0.037(2) 0.041(2) -0.0003(18) -0.001(2) -0.002(2) N10 0.060(3) 0.026(2) 0.062(3) -0.001(2) 0.007(2) -0.001(2) C1 0.047(3) 0.030(2) 0.040(2) -0.0047(19) 0.010(3) -0.008(3) C2 0.029(2) 0.036(3) 0.037(2) -0.001(2) 0.000(2) -0.002(2) C3 0.042(3) 0.072(4) 0.048(3) 0.019(3) 0.008(3) -0.001(3) C4 0.044(3) 0.031(2) 0.048(3) -0.007(2) 0.005(2) -0.013(2) C5 0.033(3) 0.043(3) 0.053(3) -0.003(2) 0.002(2) 0.003(2) C6 0.044(3) 0.071(4) 0.071(4) 0.004(4) -0.006(3) -0.004(4) C7 0.051(3) 0.061(3) 0.055(3) 0.015(3) 0.004(3) 0.004(3) C8 0.039(3) 0.031(3) 0.043(3) 0.001(2) 0.003(2) -0.005(2) C9 0.032(3) 0.035(3) 0.052(3) -0.009(2) 0.000(2) 0.001(2) C10 0.110(5) 0.040(3) 0.042(3) -0.004(3) -0.018(3) 0.000(4) C11 0.031(2) 0.029(2) 0.041(3) 0.005(2) 0.004(2) 0.002(2) C12 0.051(3) 0.035(3) 0.041(3) -0.010(2) 0.000(3) 0.004(2) C13 0.073(4) 0.030(3) 0.065(3) 0.000(2) 0.002(3) 0.004(3) C14 0.079(4) 0.042(3) 0.051(3) -0.003(3) 0.003(4) -0.001(3) Cl1 0.1229(14) 0.0640(9) 0.0699(9) 0.0142(9) -0.0160(10) -0.0205(11) Cl2' 0.067(3) 0.213(4) 0.205(4) -0.076(3) 0.005(3) -0.022(3) O21' 0.060(6) 0.257(9) 0.217(9) -0.085(8) 0.016(7) 0.001(7) O23' 0.092(6) 0.236(7) 0.235(6) -0.074(6) -0.006(6) -0.028(6) O22' 0.109(6) 0.233(7) 0.249(7) -0.076(6) -0.016(6) -0.008(6) O24' 0.128(8) 0.258(10) 0.251(9) -0.079(9) 0.005(9) -0.051(8) Cl2 0.071(2) 0.211(4) 0.241(4) -0.081(4) 0.002(3) -0.011(3) O21 0.086(5) 0.213(7) 0.229(7) -0.082(6) -0.009(6) -0.044(6) O22 0.081(6) 0.231(7) 0.232(7) -0.091(6) -0.013(6) -0.016(6) O23 0.111(8) 0.267(10) 0.256(10) -0.083(9) 0.030(8) -0.042(9) O24 0.114(8) 0.247(10) 0.329(10) -0.047(10) 0.002(9) -0.017(9) O1W 0.155(5) 0.082(3) 0.062(3) 0.016(2) -0.026(3) -0.015(3) O2W 0.115(4) 0.139(5) 0.127(4) 0.059(4) -0.040(4) 0.016(4) _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 Cd1 N4 2.345(4) . ? Cd1 N8 2.365(4) . ? Cd1 N9 2.386(4) . ? Cd1 N3 2.401(4) . ? Cd1 S2 2.5627(14) . ? Cd1 S1 2.5727(13) . ? S1 C1 1.711(5) . ? S2 C8 1.696(5) . ? N1 C1 1.307(7) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 C1 1.348(6) . ? N2 N3 1.359(6) . ? N2 H2A 0.8600 . ? N3 C2 1.293(6) . ? N4 C4 1.308(6) . ? N4 C7 1.311(6) . ? N5 C5 1.307(7) . ? N5 C6 1.314(8) . ? N6 C8 1.284(6) . ? N6 H6B 0.8600 . ? N6 H6C 0.8600 . ? N7 N8 1.353(6) . ? N7 C8 1.359(6) . ? N7 H7B 0.8600 . ? N8 C9 1.289(6) . ? N9 C14 1.295(7) . ? N9 C11 1.331(6) . ? N10 C12 1.311(6) . ? N10 C13 1.326(8) . ? C2 C3 1.471(7) . ? C2 C4 1.497(7) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.390(7) . ? C5 H5A 0.9300 . ? C6 C7 1.391(8) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C9 C11 1.469(7) . ? C9 C10 1.475(7) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.420(7) . ? C12 H12A 0.9300 . ? C13 C14 1.393(8) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? Cl1 O12' 1.389(7) . ? Cl1 O13 1.397(6) . ? Cl1 O12 1.406(6) . ? Cl1 O11 1.414(6) . ? Cl1 O14' 1.430(7) . ? Cl1 O13' 1.444(7) . ? Cl1 O11' 1.445(7) . ? Cl1 O14 1.469(6) . ? Cl2' O21' 1.401(7) . ? Cl2' O22' 1.413(8) . ? Cl2' O23' 1.419(7) . ? Cl2' O24' 1.448(8) . ? Cl2 O22 1.406(8) . ? Cl2 O21 1.426(8) . ? Cl2 O23 1.428(8) . ? Cl2 O24 1.439(8) . ? O1W H1WB 0.8500 . ? O1W H1WA 0.8499 . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cd1 N8 99.01(13) . . ? N4 Cd1 N9 88.17(15) . . ? N8 Cd1 N9 67.63(14) . . ? N4 Cd1 N3 67.03(14) . . ? N8 Cd1 N3 153.54(14) . . ? N9 Cd1 N3 88.85(13) . . ? N4 Cd1 S2 94.38(11) . . ? N8 Cd1 S2 75.19(11) . . ? N9 Cd1 S2 142.66(10) . . ? N3 Cd1 S2 126.32(10) . . ? N4 Cd1 S1 139.79(10) . . ? N8 Cd1 S1 120.77(10) . . ? N9 Cd1 S1 100.94(11) . . ? N3 Cd1 S1 74.03(10) . . ? S2 Cd1 S1 100.82(5) . . ? C1 S1 Cd1 101.34(19) . . ? C8 S2 Cd1 100.74(18) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 N3 120.8(4) . . ? C1 N2 H2A 119.6 . . ? N3 N2 H2A 119.6 . . ? C2 N3 N2 119.0(4) . . ? C2 N3 Cd1 121.7(3) . . ? N2 N3 Cd1 119.0(3) . . ? C4 N4 C7 116.6(4) . . ? C4 N4 Cd1 119.7(3) . . ? C7 N4 Cd1 123.7(3) . . ? C5 N5 C6 117.0(5) . . ? C8 N6 H6B 120.0 . . ? C8 N6 H6C 120.0 . . ? H6B N6 H6C 120.0 . . ? N8 N7 C8 120.8(4) . . ? N8 N7 H7B 119.6 . . ? C8 N7 H7B 119.6 . . ? C9 N8 N7 118.8(4) . . ? C9 N8 Cd1 122.0(3) . . ? N7 N8 Cd1 119.2(3) . . ? C14 N9 C11 117.0(4) . . ? C14 N9 Cd1 126.0(3) . . ? C11 N9 Cd1 117.0(3) . . ? C12 N10 C13 116.2(4) . . ? N1 C1 N2 116.3(4) . . ? N1 C1 S1 120.3(4) . . ? N2 C1 S1 123.4(4) . . ? N3 C2 C3 125.7(4) . . ? N3 C2 C4 112.3(4) . . ? C3 C2 C4 121.9(4) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N4 C4 C5 120.6(5) . . ? N4 C4 C2 118.8(4) . . ? C5 C4 C2 120.7(4) . . ? N5 C5 C4 122.7(5) . . ? N5 C5 H5A 118.6 . . ? C4 C5 H5A 118.6 . . ? N5 C6 C7 119.8(5) . . ? N5 C6 H6A 120.1 . . ? C7 C6 H6A 120.1 . . ? N4 C7 C6 123.1(5) . . ? N4 C7 H7A 118.5 . . ? C6 C7 H7A 118.5 . . ? N6 C8 N7 115.8(4) . . ? N6 C8 S2 120.2(4) . . ? N7 C8 S2 124.0(4) . . ? N8 C9 C11 114.3(4) . . ? N8 C9 C10 124.8(5) . . ? C11 C9 C10 120.9(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N9 C11 C12 120.1(4) . . ? N9 C11 C9 119.0(4) . . ? C12 C11 C9 120.9(4) . . ? N10 C12 C11 122.3(5) . . ? N10 C12 H12A 118.9 . . ? C11 C12 H12A 118.9 . . ? N10 C13 C14 121.4(5) . . ? N10 C13 H13A 119.3 . . ? C14 C13 H13A 119.3 . . ? N9 C14 C13 122.9(5) . . ? N9 C14 H14A 118.5 . . ? C13 C14 H14A 118.5 . . ? O12' Cl1 O13 93.7(7) . . ? O12' Cl1 O12 135.9(7) . . ? O13 Cl1 O12 113.7(4) . . ? O12' Cl1 O11 83.4(6) . . ? O13 Cl1 O11 117.5(5) . . ? O12 Cl1 O11 110.3(5) . . ? O12' Cl1 O14' 114.3(7) . . ? O13 Cl1 O14' 101.1(5) . . ? O12 Cl1 O14' 30.2(5) . . ? O11 Cl1 O14' 136.7(5) . . ? O12' Cl1 O13' 112.9(8) . . ? O13 Cl1 O13' 32.5(5) . . ? O12 Cl1 O13' 108.1(6) . . ? O11 Cl1 O13' 92.8(6) . . ? O14' Cl1 O13' 113.0(6) . . ? O12' Cl1 O11' 111.4(7) . . ? O13 Cl1 O11' 133.8(6) . . ? O12 Cl1 O11' 74.4(6) . . ? O11 Cl1 O11' 36.0(5) . . ? O14' Cl1 O11' 102.5(6) . . ? O13' Cl1 O11' 101.4(6) . . ? O12' Cl1 O14 31.5(6) . . ? O13 Cl1 O14 104.7(5) . . ? O12 Cl1 O14 105.5(5) . . ? O11 Cl1 O14 103.7(5) . . ? O14' Cl1 O14 83.1(6) . . ? O13' Cl1 O14 134.3(6) . . ? O11' Cl1 O14 117.0(6) . . ? O21' Cl2' O22' 112.4(8) . . ? O21' Cl2' O23' 110.5(7) . . ? O22' Cl2' O23' 116.1(8) . . ? O21' Cl2' O24' 104.7(8) . . ? O22' Cl2' O24' 106.0(7) . . ? O23' Cl2' O24' 106.2(8) . . ? O22 Cl2 O21 111.5(8) . . ? O22 Cl2 O23 111.3(7) . . ? O21 Cl2 O23 108.8(8) . . ? O22 Cl2 O24 113.3(9) . . ? O21 Cl2 O24 107.1(7) . . ? O23 Cl2 O24 104.5(8) . . ? H1WB O1W H1WA 110.3 . . ? H2WA O2W H2WB 95.7 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.809 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.112