# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_110323 _database_code_depnum_ccdc_archive 'CCDC 873372' #TrackingRef '110323.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 Mg N6 O8 S2' _chemical_formula_weight 492.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I-42d loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y, -z+3/4' 'x+1/2, -y, -z+3/4' '-y+1/2, -x, z+3/4' 'y+1/2, x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' '-x+1, y+1/2, -z+5/4' 'x+1, -y+1/2, -z+5/4' '-y+1, -x+1/2, z+5/4' 'y+1, x+1/2, z+5/4' _cell_length_a 16.9643(4) _cell_length_b 16.9643(4) _cell_length_c 7.6067(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2189.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1779 _cell_measurement_theta_min 2.9288 _cell_measurement_theta_max 28.7059 _exptl_crystal_description block _exptl_crystal_colour 'light orange' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93062 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlis RED(Oxford Diffraction 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur/Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2389 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_unetI/netI 0.0301 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.02 _reflns_number_total 937 _reflns_number_gt 868 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD(Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis RED(Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED(Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^)+(0.1167P)^2^+7.5299P] 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 0.00 _refine_ls_number_reflns 937 _refine_ls_number_parameters 67 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.2064 _refine_ls_wR_factor_gt 0.2037 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.186 _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 Mg1 Mg 0.5000 0.5000 0.0000 0.0189(8) Uani 1 4 d S . . S1 S 0.28243(12) 0.2500 0.1250 0.0480(9) Uani 1 2 d S . . C1 C 0.3784(4) 0.2500 0.1250 0.0245(17) Uani 1 2 d S . . O1 O 0.5348(2) 0.3807(2) 0.0169(6) 0.0278(10) Uani 1 1 d . . . N1 N 0.4230(2) 0.3135(2) 0.0777(6) 0.0209(10) Uani 1 1 d . . . H1 H 0.3980 0.3556 0.0486 0.022(16) Uiso 1 1 calc R . . C2 C 0.5038(3) 0.3168(3) 0.0720(7) 0.0217(11) Uani 1 1 d . . . C3 C 0.5458(4) 0.2500 0.1250 0.0262(17) Uani 1 2 d S . . H3 H 0.6006 0.2500 0.1250 0.016(19) Uiso 1 2 calc SR . . O2 O 0.5000 0.5000 -0.2687(8) 0.0465(17) Uani 1 2 d S . . H2 H 0.5113 0.5390 -0.3341 0.056 Uiso 1 1 d R . . N2 N 0.0276(11) 0.2500 0.1250 0.100(3) Uani 1 2 d S . . O3 O 0.0362(11) 0.1136(10) 0.005(2) 0.100(3) Uani 0.50 1 d P . . C4 C 0.071(3) 0.184(3) 0.054(4) 0.100(3) Uani 0.50 1 d P . . H4 H 0.1263 0.1857 0.0549 0.120 Uiso 0.50 1 d PR . . C5 C 0.066(2) 0.310(3) 0.145(4) 0.100(3) Uani 0.50 1 d P . . H5A H 0.0538 0.3223 0.2650 0.150 Uiso 0.50 1 d PR . . H5B H 0.0515 0.3543 0.0717 0.150 Uiso 0.50 1 d PR . . H5C H 0.1214 0.3005 0.1333 0.150 Uiso 0.50 1 d PR . . C6 C -0.0488(13) 0.2500 0.1250 0.100(3) Uani 1 2 d S . . H6A H -0.0676 0.2145 0.2137 0.150 Uiso 0.50 1 calc PR . . H6B H -0.0676 0.2333 0.0120 0.150 Uiso 0.50 1 calc PR . . H6C H -0.0676 0.3022 0.1493 0.150 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mg1 0.0157(10) 0.0157(10) 0.0253(17) 0.000 0.000 0.000 S1 0.0144(10) 0.0309(12) 0.099(2) 0.0181(14) 0.000 0.000 C1 0.024(4) 0.023(4) 0.027(4) 0.007(4) 0.000 0.000 O1 0.0182(18) 0.0164(18) 0.049(3) 0.0088(18) 0.008(2) 0.0000(16) N1 0.015(2) 0.014(2) 0.034(2) 0.0089(19) 0.0008(19) -0.0018(17) C2 0.018(2) 0.017(2) 0.030(3) 0.000(2) 0.004(2) -0.002(2) C3 0.012(4) 0.029(4) 0.038(4) 0.013(4) 0.000 0.000 O2 0.073(5) 0.035(3) 0.031(3) 0.000 0.000 -0.009(4) N2 0.123(7) 0.091(5) 0.086(6) 0.019(5) 0.000 0.000 O3 0.123(7) 0.091(5) 0.086(6) 0.019(5) 0.000 0.000 C4 0.123(7) 0.091(5) 0.086(6) 0.019(5) 0.000 0.000 C5 0.123(7) 0.091(5) 0.086(6) 0.019(5) 0.000 0.000 C6 0.123(7) 0.091(5) 0.086(6) 0.019(5) 0.000 0.000 _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 Mg1 O2 2.044(6) . ? Mg1 O2 2.044(6) 3_565 ? Mg1 O1 2.111(4) 4_655 ? Mg1 O1 2.111(4) . ? Mg1 O1 2.111(4) 2_665 ? Mg1 O1 2.111(4) 3_565 ? S1 C1 1.629(8) . ? C1 N1 1.364(6) . ? C1 N1 1.364(6) 14_454 ? O1 C2 1.275(7) . ? N1 C2 1.373(7) . ? N1 H1 0.8600 . ? C2 C3 1.398(7) . ? C3 C2 1.398(7) 14_454 ? C3 H3 0.9300 . ? O2 H2 0.8500 . ? N2 C5 1.22(4) 14_454 ? N2 C5 1.22(4) . ? N2 C6 1.30(3) . ? N2 C4 1.45(4) 14_454 ? N2 C4 1.45(4) . ? O3 C4 1.39(5) . ? O3 C5 1.58(5) 14_454 ? C4 C5 0.41(4) 14_454 ? C4 H4 0.9300 . ? C5 C4 0.41(4) 14_454 ? C5 O3 1.58(5) 14_454 ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? 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 O2 Mg1 O2 180.000(1) . 3_565 ? O2 Mg1 O1 86.51(12) . 4_655 ? O2 Mg1 O1 93.49(12) 3_565 4_655 ? O2 Mg1 O1 93.49(12) . . ? O2 Mg1 O1 86.51(12) 3_565 . ? O1 Mg1 O1 90.213(15) 4_655 . ? O2 Mg1 O1 93.49(12) . 2_665 ? O2 Mg1 O1 86.51(12) 3_565 2_665 ? O1 Mg1 O1 90.213(15) 4_655 2_665 ? O1 Mg1 O1 173.0(2) . 2_665 ? O2 Mg1 O1 86.51(12) . 3_565 ? O2 Mg1 O1 93.49(12) 3_565 3_565 ? O1 Mg1 O1 173.0(2) 4_655 3_565 ? O1 Mg1 O1 90.213(15) . 3_565 ? O1 Mg1 O1 90.213(16) 2_665 3_565 ? N1 C1 N1 112.7(6) . 14_454 ? N1 C1 S1 123.7(3) . . ? N1 C1 S1 123.7(3) 14_454 . ? C2 O1 Mg1 136.0(4) . . ? C1 N1 C2 126.5(5) . . ? C1 N1 H1 116.8 . . ? C2 N1 H1 116.8 . . ? O1 C2 N1 117.2(4) . . ? O1 C2 C3 125.1(5) . . ? N1 C2 C3 117.7(5) . . ? C2 C3 C2 118.8(7) . 14_454 ? C2 C3 H3 120.6 . . ? C2 C3 H3 120.6 14_454 . ? Mg1 O2 H2 125.8 . . ? C5 N2 C5 116(5) 14_454 . ? C5 N2 C6 122(2) 14_454 . ? C5 N2 C6 122(2) . . ? C5 N2 C4 115(2) 14_454 14_454 ? C5 N2 C4 15(2) . 14_454 ? C6 N2 C4 121(2) . 14_454 ? C5 N2 C4 15(2) 14_454 . ? C5 N2 C4 115(2) . . ? C6 N2 C4 121(2) . . ? C4 N2 C4 118(4) 14_454 . ? C4 O3 C5 14(2) . 14_454 ? C5 C4 O3 110(10) 14_454 . ? C5 C4 N2 50(10) 14_454 . ? O3 C4 N2 123(3) . . ? C5 C4 H4 101.0 14_454 . ? O3 C4 H4 117.2 . . ? N2 C4 H4 119.4 . . ? C4 C5 N2 115(10) 14_454 . ? C4 C5 O3 56(10) 14_454 14_454 ? N2 C5 O3 125(3) . 14_454 ? C4 C5 H5A 24.0 14_454 . ? N2 C5 H5A 100.2 . . ? O3 C5 H5A 45.7 14_454 . ? C4 C5 H5B 114.0 14_454 . ? N2 C5 H5B 116.3 . . ? O3 C5 H5B 64.1 14_454 . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 86.0 14_454 . ? N2 C5 H5C 111.4 . . ? O3 C5 H5C 119.9 14_454 . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.754 _refine_diff_density_min -0.707 _refine_diff_density_rms 0.105 data_1230 _database_code_depnum_ccdc_archive 'CCDC 873373' #TrackingRef '110323.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 N6 Ni O8 S2' _chemical_formula_weight 527.22 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' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I-42d loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y, -z+3/4' 'x+1/2, -y, -z+3/4' '-y+1/2, -x, z+3/4' 'y+1/2, x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' '-x+1, y+1/2, -z+5/4' 'x+1, -y+1/2, -z+5/4' '-y+1, -x+1/2, z+5/4' 'y+1, x+1/2, z+5/4' _cell_length_a 16.8944(2) _cell_length_b 16.8944(2) _cell_length_c 7.5454(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2153.61(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1942 _cell_measurement_theta_min 2.4062 _cell_measurement_theta_max 28.7943 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 1.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.87628 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlis RED(Oxford Diffraction 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur/Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2331 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_unetI/netI 0.0285 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.02 _reflns_number_total 839 _reflns_number_gt 790 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD(Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis RED(Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED(Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^)+(0.1156P)^2^+7.1047P] 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 0.00(6) _refine_ls_number_reflns 839 _refine_ls_number_parameters 66 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1746 _refine_ls_wR_factor_gt 0.1729 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.165 _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 Ni1 Ni 0.5000 0.5000 0.0000 0.0204(5) Uani 1 4 d S . . S1 S 0.28287(14) 0.2500 0.1250 0.0479(10) Uani 1 2 d S . . C1 C 0.3801(5) 0.2500 0.1250 0.024(2) Uani 1 2 d S . . O1 O 0.5363(2) 0.3808(2) 0.0165(9) 0.0295(13) Uani 1 1 d . . . N1 N 0.4236(3) 0.3135(3) 0.0745(8) 0.0233(14) Uani 1 1 d . . . H1 H 0.3981 0.3550 0.0411 0.028 Uiso 1 1 calc R . . C2 C 0.5067(4) 0.3174(3) 0.0722(9) 0.0189(13) Uani 1 1 d . . . C3 C 0.5475(5) 0.2500 0.1250 0.023(2) Uani 1 2 d S . . H3 H 0.6026 0.2500 0.1250 0.028 Uiso 1 2 calc SR . . O2 O 0.5000(5) 0.5000 -0.2664 0.050(2) Uani 1 2 d SR . . H2 H 0.5118 0.5390 -0.3345 0.060 Uiso 1 1 d R . . N2 N 0.032(2) 0.2500 0.1250 0.141(6) Uani 1 2 d S . . O3 O 0.0234(19) 0.1181(13) 0.003(4) 0.141(6) Uani 0.50 1 d PD . . C4 C 0.063(4) 0.183(3) 0.048(9) 0.141(6) Uani 0.50 1 d PD . . H4 H 0.1180 0.1852 0.0702 0.169 Uiso 0.50 1 d PR . . C5 C 0.070(4) 0.304(3) 0.153(8) 0.141(6) Uani 0.50 1 d P . . H5A H 0.0634 0.3274 0.2955 0.212 Uiso 0.50 1 d PR . . H5B H 0.0611 0.3594 0.1023 0.212 Uiso 0.50 1 d PR . . H5C H 0.1311 0.3057 0.1638 0.212 Uiso 0.50 1 d PR . . C6 C -0.052(2) 0.2500 0.1250 0.141(6) Uani 1 2 d S . . H6A H -0.0714 0.2088 0.0485 0.212 Uiso 0.50 1 calc PR . . H6B H -0.0714 0.3002 0.0833 0.212 Uiso 0.50 1 calc PR . . H6C H -0.0714 0.2410 0.2433 0.212 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0162(6) 0.0162(6) 0.0288(10) 0.000 0.000 0.000 S1 0.0125(12) 0.0300(14) 0.101(3) 0.0203(16) 0.000 0.000 C1 0.023(5) 0.019(4) 0.029(7) 0.007(4) 0.000 0.000 O1 0.015(2) 0.018(2) 0.056(4) 0.009(2) 0.005(2) -0.0002(18) N1 0.017(3) 0.013(3) 0.040(4) 0.007(2) 0.001(2) 0.003(2) C2 0.012(3) 0.014(3) 0.031(4) 0.001(2) 0.005(3) -0.006(3) C3 0.009(4) 0.028(5) 0.032(6) 0.010(4) 0.000 0.000 O2 0.081(6) 0.040(4) 0.029(5) 0.000 0.000 -0.023(6) N2 0.244(17) 0.084(7) 0.095(12) 0.022(7) 0.000 0.000 O3 0.244(17) 0.084(7) 0.095(12) 0.022(7) 0.000 0.000 C4 0.244(17) 0.084(7) 0.095(12) 0.022(7) 0.000 0.000 C5 0.244(17) 0.084(7) 0.095(12) 0.022(7) 0.000 0.000 C6 0.244(17) 0.084(7) 0.095(12) 0.022(7) 0.000 0.000 _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 O2 2.0098 3_565 ? Ni1 O2 2.0098 . ? Ni1 O1 2.109(4) 2_665 ? Ni1 O1 2.109(4) 4_655 ? Ni1 O1 2.109(4) . ? Ni1 O1 2.109(4) 3_565 ? S1 C1 1.643(9) . ? C1 N1 1.355(7) . ? C1 N1 1.355(7) 14_454 ? O1 C2 1.255(8) . ? N1 C2 1.405(8) . ? N1 H1 0.8600 . ? C2 C3 1.390(7) . ? C3 C2 1.390(7) 14_454 ? C3 H3 0.9300 . ? O2 H2 0.8596 . ? N2 C5 1.14(7) . ? N2 C5 1.14(7) 14_454 ? N2 C4 1.38(6) 14_454 ? N2 C4 1.38(6) . ? N2 C6 1.43(4) . ? O3 C4 1.33(2) . ? O3 C5 1.68(6) 14_454 ? C4 C5 0.44(8) 14_454 ? C4 H4 0.9428 . ? C5 C4 0.44(8) 14_454 ? C5 O3 1.68(6) 14_454 ? C5 C5 1.89(10) 14_454 ? C5 H5A 1.1489 . ? C5 H5B 1.0137 . ? C5 H5C 1.0370 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? 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 O2 Ni1 O2 180.0(4) 3_565 . ? O2 Ni1 O1 86.6(3) 3_565 2_665 ? O2 Ni1 O1 93.38(19) . 2_665 ? O2 Ni1 O1 93.38(19) 3_565 4_655 ? O2 Ni1 O1 86.6(3) . 4_655 ? O1 Ni1 O1 90.20(2) 2_665 4_655 ? O2 Ni1 O1 86.6(3) 3_565 . ? O2 Ni1 O1 93.38(19) . . ? O1 Ni1 O1 173.2(4) 2_665 . ? O1 Ni1 O1 90.20(2) 4_655 . ? O2 Ni1 O1 93.38(19) 3_565 3_565 ? O2 Ni1 O1 86.6(3) . 3_565 ? O1 Ni1 O1 90.20(2) 2_665 3_565 ? O1 Ni1 O1 173.2(4) 4_655 3_565 ? O1 Ni1 O1 90.20(2) . 3_565 ? N1 C1 N1 114.4(8) . 14_454 ? N1 C1 S1 122.8(4) . . ? N1 C1 S1 122.8(4) 14_454 . ? C2 O1 Ni1 135.9(4) . . ? C1 N1 C2 125.6(5) . . ? C1 N1 H1 117.2 . . ? C2 N1 H1 117.2 . . ? O1 C2 C3 126.6(6) . . ? O1 C2 N1 116.3(5) . . ? C3 C2 N1 117.0(5) . . ? C2 C3 C2 120.4(8) . 14_454 ? C2 C3 H3 119.8 . . ? C2 C3 H3 119.8 14_454 . ? Ni1 O2 H2 126.7 . . ? C5 N2 C5 112(7) . 14_454 ? C5 N2 C4 17(6) . 14_454 ? C5 N2 C4 122(4) 14_454 14_454 ? C5 N2 C4 122(4) . . ? C5 N2 C4 17(6) 14_454 . ? C4 N2 C4 136(6) 14_454 . ? C5 N2 C6 124(4) . . ? C5 N2 C6 124(4) 14_454 . ? C4 N2 C6 112(3) 14_454 . ? C4 N2 C6 112(3) . . ? C4 O3 C5 10(5) . 14_454 ? C5 C4 O3 139(10) 14_454 . ? C5 C4 N2 49(10) 14_454 . ? O3 C4 N2 127(6) . . ? C5 C4 H4 65.0 14_454 . ? O3 C4 H4 125.5 . . ? N2 C4 H4 105.1 . . ? C4 C5 N2 114(10) 14_454 . ? C4 C5 O3 31(10) 14_454 14_454 ? N2 C5 O3 117(6) . 14_454 ? C4 C5 C5 131(10) 14_454 14_454 ? N2 C5 C5 34(4) . 14_454 ? O3 C5 C5 148(4) 14_454 14_454 ? C4 C5 H5A 14.1 14_454 . ? N2 C5 H5A 113.1 . . ? O3 C5 H5A 45.3 14_454 . ? C5 C5 H5A 122.5 14_454 . ? C4 C5 H5B 80.2 14_454 . ? N2 C5 H5B 126.1 . . ? O3 C5 H5B 51.8 14_454 . ? C5 C5 H5B 143.9 14_454 . ? H5A C5 H5B 91.8 . . ? C4 C5 H5C 100.4 14_454 . ? N2 C5 H5C 127.0 . . ? O3 C5 H5C 114.6 14_454 . ? C5 C5 H5C 92.1 14_454 . ? H5A C5 H5C 90.8 . . ? H5B C5 H5C 99.1 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 0.771 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.117 data_20101123 _database_code_depnum_ccdc_archive 'CCDC 873374' #TrackingRef '110323.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H6 Co N4 O6 S2' _chemical_formula_weight 377.22 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' Co Co 0.3494 0.9721 '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 6.8866(6) _cell_length_b 7.0305(6) _cell_length_c 7.2471(6) _cell_angle_alpha 91.537(7) _cell_angle_beta 102.694(7) _cell_angle_gamma 113.507(8) _cell_volume 311.31(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1296 _cell_measurement_theta_min 2.8992 _cell_measurement_theta_max 26.3251 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.012 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 189 _exptl_absorpt_coefficient_mu 1.748 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91524 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlis RED(Oxford Diffraction 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur/Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2160 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_unetI/netI 0.0495 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.04 _reflns_number_total 1008 _reflns_number_gt 801 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD(Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlis RED(Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED(Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^)+(0.0401P)^2^+0.1979P] 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 1008 _refine_ls_number_parameters 97 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 Co1 Co 0.5000 0.5000 0.5000 0.0180(3) Uani 1 2 d S . . S1 S 0.80507(16) 0.37870(15) -0.32519(13) 0.0211(3) Uani 1 1 d . . . O1 O 0.8990(4) -0.0278(4) 0.2017(4) 0.0225(7) Uani 1 1 d . . . O2 O 0.5046(4) 0.3863(4) 0.2263(4) 0.0226(7) Uani 1 1 d . . . O3 O 0.2568(4) 0.2205(4) 0.5120(4) 0.0262(7) Uani 1 1 d . . . N1 N 0.8459(5) 0.1691(5) -0.0299(4) 0.0164(7) Uani 1 1 d . . . H1 H 0.9251 0.1306 -0.0853 0.020 Uiso 1 1 calc R . . N2 N 0.6511(5) 0.3635(5) -0.0183(4) 0.0171(7) Uani 1 1 d . . . H2 H 0.5999 0.4490 -0.0679 0.020 Uiso 1 1 calc R . . C2 C 0.6823(6) 0.1570(6) 0.2283(5) 0.0169(9) Uani 1 1 d . . . H2A H 0.6456 0.1008 0.3370 0.020 Uiso 1 1 calc R . . C1 C 0.8109(6) 0.0937(6) 0.1391(5) 0.0179(9) Uani 1 1 d . . . C3 C 0.6100(6) 0.3028(6) 0.1552(5) 0.0166(9) Uani 1 1 d . . . C4 C 0.7638(6) 0.2994(6) -0.1141(5) 0.0155(9) 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 Co1 0.0224(5) 0.0189(5) 0.0153(4) 0.0049(3) 0.0097(3) 0.0084(3) S1 0.0274(6) 0.0299(6) 0.0147(6) 0.0096(4) 0.0114(5) 0.0172(5) O1 0.0323(16) 0.0279(16) 0.0231(16) 0.0139(13) 0.0133(13) 0.0245(14) O2 0.0383(17) 0.0310(17) 0.0161(15) 0.0082(12) 0.0153(13) 0.0274(14) O3 0.0266(16) 0.0232(16) 0.0229(16) 0.0100(12) 0.0071(13) 0.0035(13) N1 0.0217(18) 0.0213(18) 0.0147(17) 0.0062(14) 0.0086(14) 0.0151(15) N2 0.0249(19) 0.0227(19) 0.0156(18) 0.0122(14) 0.0108(15) 0.0184(15) C2 0.024(2) 0.018(2) 0.012(2) 0.0059(16) 0.0083(17) 0.0097(17) C1 0.021(2) 0.017(2) 0.016(2) 0.0011(17) 0.0041(17) 0.0083(17) C3 0.019(2) 0.018(2) 0.013(2) 0.0002(16) 0.0036(17) 0.0092(17) C4 0.017(2) 0.014(2) 0.015(2) 0.0004(16) 0.0057(17) 0.0048(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O3 2.030(2) . ? Co1 O3 2.030(2) 2_666 ? Co1 O2 2.130(2) . ? Co1 O2 2.130(2) 2_666 ? Co1 S1 2.6577(10) 1_556 ? Co1 S1 2.6577(10) 2_665 ? S1 C4 1.686(4) . ? S1 Co1 2.6577(10) 1_554 ? O1 C1 1.272(4) . ? O2 C3 1.274(4) . ? N1 C4 1.351(5) . ? N1 C1 1.379(5) . ? N1 H1 0.8600 . ? N2 C4 1.337(4) . ? N2 C3 1.390(5) . ? N2 H2 0.8600 . ? C2 C3 1.378(5) . ? C2 C1 1.396(5) . ? C2 H2A 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 O3 Co1 O3 180.00(12) . 2_666 ? O3 Co1 O2 89.96(11) . . ? O3 Co1 O2 90.04(11) 2_666 . ? O3 Co1 O2 90.04(11) . 2_666 ? O3 Co1 O2 89.96(11) 2_666 2_666 ? O2 Co1 O2 180.000(1) . 2_666 ? O3 Co1 S1 91.71(8) . 1_556 ? O3 Co1 S1 88.29(8) 2_666 1_556 ? O2 Co1 S1 91.97(7) . 1_556 ? O2 Co1 S1 88.03(7) 2_666 1_556 ? O3 Co1 S1 88.29(8) . 2_665 ? O3 Co1 S1 91.71(8) 2_666 2_665 ? O2 Co1 S1 88.03(7) . 2_665 ? O2 Co1 S1 91.97(7) 2_666 2_665 ? S1 Co1 S1 180.0 1_556 2_665 ? C4 S1 Co1 111.10(13) . 1_554 ? C3 O2 Co1 138.4(2) . . ? C4 N1 C1 124.2(3) . . ? C4 N1 H1 117.9 . . ? C1 N1 H1 117.9 . . ? C4 N2 C3 125.2(3) . . ? C4 N2 H2 117.4 . . ? C3 N2 H2 117.4 . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? O1 C1 N1 117.3(3) . . ? O1 C1 C2 125.1(4) . . ? N1 C1 C2 117.6(4) . . ? O2 C3 C2 127.5(3) . . ? O2 C3 N2 115.5(3) . . ? C2 C3 N2 116.9(3) . . ? N2 C4 N1 115.8(3) . . ? N2 C4 S1 122.4(3) . . ? N1 C4 S1 121.8(3) . . ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.915 _refine_diff_density_max 0.566 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.078 #===END