# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Lijuan Li' _publ_contact_author_email LLI@CSULB.EDU _publ_section_title ; Neutral and Reduced Roussin's Red salt Ester [Fe2(\m-RS)2(NO)4] (R = n-Pr, t-Bu, 6-methyl-2-pyridyl and 4,6-dimethyl-2-pyrimidyl): Synthesis, X-ray Crystal Structures, Spectroscopic, Electrochemical and Density Functional Theoretical Investigations ; loop_ _publ_author_name 'Lijuan Li.' 'Miguel A Camacho-Fernandez' 'Rongming Wang.' 'Wei Xu.' ; Jian Zhang ; # Attachment 'compound_1,3,4.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 691873' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H14 Fe2 N4 O4 S2' _chemical_formula_weight 382.05 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.0016(5) _cell_length_b 7.9562(9) _cell_length_c 9.4709(9) _cell_angle_alpha 77.803(7) _cell_angle_beta 80.488(7) _cell_angle_gamma 79.337(7) _cell_volume 358.88(7) _cell_formula_units_Z 1 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 78 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 25.19 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max .18 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 194 _exptl_absorpt_coefficient_mu 2.321 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min .652 _exptl_absorpt_correction_T_max .831 _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 2615 _diffrn_reflns_av_R_equivalents 0.0844 _diffrn_reflns_av_sigmaI/netI 0.0972 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.19 _reflns_number_total 1263 _reflns_number_gt 942 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART & SAINT' _computing_data_reduction 'Siemens XPREP' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens 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^)+(0.0641P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1263 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_ref 0.0677 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _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 Fe1 Fe 0.00008(15) 0.62385(10) 0.37827(9) 0.0249(3) Uani 1 1 d . . . S1 S -0.1879(3) 0.37828(19) 0.42027(16) 0.0279(4) Uani 1 1 d . . . O1 O -0.4068(9) 0.9229(6) 0.3387(5) 0.0474(13) Uani 1 1 d . . . O2 O 0.4082(9) 0.6099(7) 0.1334(5) 0.0474(13) Uani 1 1 d . . . N1 N -0.2525(10) 0.7930(7) 0.3652(5) 0.0317(12) Uani 1 1 d . . . N2 N 0.2543(10) 0.6066(6) 0.2404(5) 0.0314(12) Uani 1 1 d . . . C1 C 0.0490(12) 0.2265(8) 0.3192(6) 0.0281(13) Uani 1 1 d . . . H1A H 0.2364 0.2417 0.3209 0.034 Uiso 1 1 calc R . . H1B H 0.0288 0.1079 0.3660 0.034 Uiso 1 1 calc R . . C2 C -0.0070(12) 0.2568(8) 0.1628(6) 0.0338(15) Uani 1 1 d . . . H2A H 0.0163 0.3748 0.1156 0.041 Uiso 1 1 calc R . . H2B H -0.1954 0.2437 0.1613 0.041 Uiso 1 1 calc R . . C3 C 0.1859(13) 0.1289(9) 0.0789(7) 0.0378(16) Uani 1 1 d . . . H3A H 0.1442 0.1499 -0.0192 0.057 Uiso 1 1 calc R . . H3B H 0.1628 0.0120 0.1254 0.057 Uiso 1 1 calc R . . H3C H 0.3722 0.1442 0.0778 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0174(5) 0.0265(5) 0.0282(5) -0.0018(4) -0.0015(3) -0.0020(3) S1 0.0198(8) 0.0306(9) 0.0318(8) -0.0032(7) -0.0033(6) -0.0028(6) O1 0.032(3) 0.033(3) 0.070(3) 0.000(3) -0.010(2) 0.005(2) O2 0.034(3) 0.069(4) 0.033(3) -0.005(2) 0.011(2) -0.008(2) N1 0.025(3) 0.030(3) 0.037(3) -0.002(2) -0.006(2) -0.001(2) N2 0.027(3) 0.031(3) 0.035(3) -0.002(2) -0.004(3) -0.005(2) C1 0.030(3) 0.024(3) 0.029(3) -0.004(3) -0.005(3) -0.003(2) C2 0.032(4) 0.035(4) 0.033(3) -0.002(3) -0.006(3) -0.005(3) C3 0.037(4) 0.045(4) 0.034(4) -0.010(3) -0.004(3) -0.010(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 Fe1 N1 1.666(5) . ? Fe1 N2 1.674(5) . ? Fe1 S1 2.2556(17) . ? Fe1 S1 2.2575(17) 2_566 ? Fe1 Fe1 2.6983(17) 2_566 ? S1 C1 1.834(5) . ? S1 Fe1 2.2575(17) 2_566 ? O1 N1 1.177(6) . ? O2 N2 1.166(6) . ? C1 C2 1.514(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.524(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 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 N1 Fe1 N2 120.2(3) . . ? N1 Fe1 S1 108.13(18) . . ? N2 Fe1 S1 106.45(17) . . ? N1 Fe1 S1 106.71(18) . 2_566 ? N2 Fe1 S1 108.10(18) . 2_566 ? S1 Fe1 S1 106.56(6) . 2_566 ? N1 Fe1 Fe1 120.04(18) . 2_566 ? N2 Fe1 Fe1 119.78(17) . 2_566 ? S1 Fe1 Fe1 53.31(5) . 2_566 ? S1 Fe1 Fe1 53.25(5) 2_566 2_566 ? C1 S1 Fe1 106.4(2) . . ? C1 S1 Fe1 106.35(19) . 2_566 ? Fe1 S1 Fe1 73.44(6) . 2_566 ? O1 N1 Fe1 170.3(5) . . ? O2 N2 Fe1 171.1(5) . . ? C2 C1 S1 111.0(4) . . ? C2 C1 H1A 109.4 . . ? S1 C1 H1A 109.4 . . ? C2 C1 H1B 109.4 . . ? S1 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? C1 C2 C3 111.2(5) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.111 _refine_diff_density_min -0.591 _refine_diff_density_rms 0.151 #end data_3 _database_code_depnum_ccdc_archive 'CCDC 691874' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Fe2 N6 O4 S2' _chemical_formula_weight 480.11 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' Fe Fe 0.3463 0.8444 '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 6.3865(7) _cell_length_b 7.0898(8) _cell_length_c 10.6042(13) _cell_angle_alpha 73.929(7) _cell_angle_beta 87.184(7) _cell_angle_gamma 70.935(7) _cell_volume 435.62(9) _cell_formula_units_Z 1 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2142 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max .16 _exptl_crystal_size_mid .13 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.830 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 242 _exptl_absorpt_coefficient_mu 1.937 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.85 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3566 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.13 _reflns_number_total 1440 _reflns_number_gt 1280 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1440 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 Fe1 Fe 0.38216(6) 0.52543(6) 0.10723(4) 0.01634(17) Uani 1 1 d . . . S1 S 0.54672(11) 0.22164(10) 0.05587(7) 0.0177(2) Uani 1 1 d . . . O1 O -0.0689(3) 0.5809(4) 0.1553(2) 0.0346(6) Uani 1 1 d . . . O2 O 0.5894(4) 0.4906(4) 0.3465(2) 0.0330(6) Uani 1 1 d . . . N1 N 0.1126(4) 0.5568(3) 0.1222(2) 0.0206(6) Uani 1 1 d . . . N2 N 0.5219(4) 0.5058(3) 0.2424(2) 0.0193(6) Uani 1 1 d . . . N3 N 0.7016(4) -0.0194(3) 0.2904(2) 0.0196(6) Uani 1 1 d . . . C1 C 0.7705(4) 0.0800(4) 0.1794(3) 0.0167(6) Uani 1 1 d . . . C2 C 0.9875(5) 0.0755(4) 0.1583(3) 0.0210(7) Uani 1 1 d . . . H2A H 1.0274 0.1468 0.0784 0.025 Uiso 1 1 calc R . . C3 C 1.1433(5) -0.0398(4) 0.2612(3) 0.0229(7) Uani 1 1 d . . . H3A H 1.2909 -0.0467 0.2515 0.027 Uiso 1 1 calc R . . C4 C 1.0765(5) -0.1439(4) 0.3781(3) 0.0232(7) Uani 1 1 d . . . H4A H 1.1790 -0.2212 0.4478 0.028 Uiso 1 1 calc R . . C5 C 0.8552(5) -0.1327(4) 0.3909(3) 0.0209(7) Uani 1 1 d . . . C6 C 0.7734(5) -0.2432(5) 0.5151(3) 0.0294(8) Uani 1 1 d . . . H6A H 0.6171 -0.2164 0.5045 0.044 Uiso 1 1 calc R . . H6B H 0.8011 -0.1940 0.5863 0.044 Uiso 1 1 calc R . . H6C H 0.8498 -0.3898 0.5340 0.044 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 Fe1 0.0128(2) 0.0182(2) 0.0157(3) -0.00313(18) -0.00047(18) -0.00315(17) S1 0.0156(4) 0.0165(4) 0.0192(4) -0.0026(3) -0.0022(3) -0.0043(3) O1 0.0176(12) 0.0408(13) 0.0417(14) -0.0060(11) 0.0055(10) -0.0097(10) O2 0.0335(13) 0.0467(14) 0.0206(12) -0.0071(11) -0.0046(10) -0.0164(11) N1 0.0188(13) 0.0207(12) 0.0200(13) -0.0029(11) -0.0016(11) -0.0054(10) N2 0.0163(12) 0.0201(12) 0.0195(14) -0.0040(11) 0.0005(11) -0.0046(10) N3 0.0194(12) 0.0157(12) 0.0220(14) -0.0043(11) -0.0020(11) -0.0038(9) C1 0.0168(14) 0.0128(13) 0.0183(15) -0.0054(12) -0.0014(12) -0.0005(10) C2 0.0176(14) 0.0193(14) 0.0210(16) -0.0004(13) 0.0002(12) -0.0034(11) C3 0.0169(14) 0.0207(14) 0.0290(17) -0.0061(13) -0.0008(13) -0.0038(11) C4 0.0228(15) 0.0185(14) 0.0229(16) -0.0042(13) -0.0065(13) 0.0001(11) C5 0.0250(15) 0.0149(13) 0.0211(16) -0.0052(12) -0.0021(13) -0.0038(11) C6 0.0337(18) 0.0246(16) 0.0278(18) -0.0019(14) -0.0024(15) -0.0108(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N1 1.668(2) . ? Fe1 N2 1.675(2) . ? Fe1 S1 2.2696(7) 2_665 ? Fe1 S1 2.2703(9) . ? Fe1 Fe1 2.7076(9) 2_665 ? S1 C1 1.812(3) . ? S1 Fe1 2.2696(7) 2_665 ? O1 N1 1.166(3) . ? O2 N2 1.169(3) . ? N3 C1 1.330(4) . ? N3 C5 1.362(3) . ? C1 C2 1.384(4) . ? C2 C3 1.389(4) . ? C2 H2A 0.9300 . ? C3 C4 1.382(4) . ? C3 H3A 0.9300 . ? C4 C5 1.391(4) . ? C4 H4A 0.9300 . ? C5 C6 1.500(4) . ? 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 N1 Fe1 N2 116.11(12) . . ? N1 Fe1 S1 113.52(8) . 2_665 ? N2 Fe1 S1 106.62(7) . 2_665 ? N1 Fe1 S1 107.86(9) . . ? N2 Fe1 S1 105.28(8) . . ? S1 Fe1 S1 106.78(3) 2_665 . ? N1 Fe1 Fe1 126.28(9) . 2_665 ? N2 Fe1 Fe1 117.43(9) . 2_665 ? S1 Fe1 Fe1 53.40(2) 2_665 2_665 ? S1 Fe1 Fe1 53.38(2) . 2_665 ? C1 S1 Fe1 114.26(9) . 2_665 ? C1 S1 Fe1 104.08(10) . . ? Fe1 S1 Fe1 73.22(3) 2_665 . ? O1 N1 Fe1 167.6(2) . . ? O2 N2 Fe1 169.4(2) . . ? C1 N3 C5 117.7(2) . . ? N3 C1 C2 124.6(2) . . ? N3 C1 S1 112.13(19) . . ? C2 C1 S1 123.2(2) . . ? C1 C2 C3 117.4(3) . . ? C1 C2 H2A 121.3 . . ? C3 C2 H2A 121.3 . . ? C4 C3 C2 119.3(3) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 119.7(2) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? N3 C5 C4 121.3(2) . . ? N3 C5 C6 116.7(2) . . ? C4 C5 C6 122.0(2) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.557 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.080 #end data_4 _database_code_depnum_ccdc_archive 'CCDC 691875' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Fe2 N8 O4 S2' _chemical_formula_weight 510.13 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 19.9018(1) _cell_length_b 19.9018(1) _cell_length_c 10.0627(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3985.65(5) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4285 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 28.02 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max .17 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.700 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 1.702 _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 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17082 _diffrn_reflns_av_R_equivalents 0.0880 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 29.34 _reflns_number_total 2736 _reflns_number_gt 1925 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2736 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 0.917 _refine_ls_restrained_S_all 0.917 _refine_ls_shift/su_max 0.002 _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 Fe1 Fe 0.939571(13) 0.467756(14) 0.01426(3) 0.03752(11) Uani 1 1 d . . . S1 S 1.01385(2) 0.45618(2) -0.15630(5) 0.03859(14) Uani 1 1 d . . . N4 N 0.93091(8) 0.46196(8) -0.36028(18) 0.0408(4) Uani 1 1 d . . . N3 N 0.98898(8) 0.56374(8) -0.31000(19) 0.0417(4) Uani 1 1 d . . . C6 C 0.97281(9) 0.50004(10) -0.2906(2) 0.0343(4) Uani 1 1 d . . . N2 N 0.87084(9) 0.50107(9) -0.05412(19) 0.0465(4) Uani 1 1 d . . . N1 N 0.93143(9) 0.39359(9) 0.08882(19) 0.0512(5) Uani 1 1 d . . . C5 C 0.95695(11) 0.59442(10) -0.4113(2) 0.0454(5) Uani 1 1 d . . . C4 C 0.89906(10) 0.49332(11) -0.4614(2) 0.0443(5) Uani 1 1 d . . . O1 O 0.91594(11) 0.34257(9) 0.1371(2) 0.0841(6) Uani 1 1 d . . . O2 O 0.81892(8) 0.51355(10) -0.1017(2) 0.0749(5) Uani 1 1 d . . . C2 C 0.85338(12) 0.45186(14) -0.5458(3) 0.0644(7) Uani 1 1 d . . . H2A H 0.8525 0.4066 -0.5130 0.097 Uiso 1 1 calc R . . H2B H 0.8694 0.4520 -0.6358 0.097 Uiso 1 1 calc R . . H2C H 0.8088 0.4703 -0.5430 0.097 Uiso 1 1 calc R . . C1 C 0.91006(11) 0.56061(12) -0.4861(2) 0.0484(5) Uani 1 1 d . . . H1A H 0.8862 0.5827 -0.5524 0.058 Uiso 1 1 calc R . . C3 C 0.97587(14) 0.66586(12) -0.4385(3) 0.0692(7) Uani 1 1 d . . . H3A H 1.0093 0.6800 -0.3757 0.104 Uiso 1 1 calc R . . H3B H 0.9368 0.6939 -0.4304 0.104 Uiso 1 1 calc R . . H3C H 0.9936 0.6695 -0.5269 0.104 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 Fe1 0.03358(16) 0.04650(18) 0.03248(19) 0.00192(13) -0.00318(12) -0.00317(11) S1 0.0398(3) 0.0425(3) 0.0335(3) -0.0011(2) -0.0030(2) 0.0050(2) N4 0.0392(9) 0.0506(10) 0.0325(10) 0.0024(8) -0.0008(8) -0.0059(7) N3 0.0493(10) 0.0416(9) 0.0343(11) -0.0014(8) -0.0034(8) 0.0001(7) C6 0.0355(9) 0.0420(10) 0.0253(10) -0.0015(9) 0.0026(8) 0.0034(8) N2 0.0400(9) 0.0613(11) 0.0380(11) 0.0011(9) -0.0009(8) 0.0014(8) N1 0.0598(11) 0.0535(11) 0.0402(12) 0.0038(10) -0.0106(9) -0.0152(9) C5 0.0540(12) 0.0446(11) 0.0375(13) 0.0035(10) 0.0020(11) 0.0049(9) C4 0.0362(10) 0.0669(14) 0.0298(12) 0.0014(10) 0.0011(9) -0.0053(9) O1 0.1175(16) 0.0670(11) 0.0679(13) 0.0178(11) -0.0189(12) -0.0397(11) O2 0.0482(10) 0.1027(14) 0.0739(14) 0.0072(11) -0.0188(10) 0.0151(9) C2 0.0572(15) 0.0914(19) 0.0446(15) 0.0093(14) -0.0152(12) -0.0234(13) C1 0.0487(12) 0.0611(13) 0.0355(13) 0.0094(11) -0.0057(10) 0.0046(10) C3 0.0920(19) 0.0493(14) 0.0663(19) 0.0139(13) -0.0107(16) -0.0039(12) _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 Fe1 N1 1.6637(19) . ? Fe1 N2 1.6686(18) . ? Fe1 S1 2.2768(6) . ? Fe1 S1 2.2790(6) 9_765 ? Fe1 Fe1 2.7413(5) 9_765 ? S1 C6 1.804(2) . ? S1 Fe1 2.2790(6) 9_765 ? N4 C6 1.327(2) . ? N4 C4 1.351(3) . ? N3 C6 1.322(2) . ? N3 C5 1.348(3) . ? N2 O2 1.165(2) . ? N1 O1 1.167(2) . ? C5 C1 1.375(3) . ? C5 C3 1.496(3) . ? C4 C1 1.380(3) . ? C4 C2 1.493(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C1 H1A 0.9300 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 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 N1 Fe1 N2 117.30(9) . . ? N1 Fe1 S1 108.26(7) . . ? N2 Fe1 S1 105.16(7) . . ? N1 Fe1 S1 110.25(7) . 9_765 ? N2 Fe1 S1 109.15(7) . 9_765 ? S1 Fe1 S1 106.013(19) . 9_765 ? N1 Fe1 Fe1 123.23(6) . 9_765 ? N2 Fe1 Fe1 119.34(6) . 9_765 ? S1 Fe1 Fe1 53.042(16) . 9_765 ? S1 Fe1 Fe1 52.970(16) 9_765 9_765 ? C6 S1 Fe1 102.81(6) . . ? C6 S1 Fe1 109.42(7) . 9_765 ? Fe1 S1 Fe1 73.987(19) . 9_765 ? C6 N4 C4 115.38(17) . . ? C6 N3 C5 115.51(18) . . ? N3 C6 N4 128.49(18) . . ? N3 C6 S1 117.66(14) . . ? N4 C6 S1 113.82(15) . . ? O2 N2 Fe1 168.75(17) . . ? O1 N1 Fe1 170.17(19) . . ? N3 C5 C1 120.88(19) . . ? N3 C5 C3 116.7(2) . . ? C1 C5 C3 122.4(2) . . ? N4 C4 C1 120.66(19) . . ? N4 C4 C2 117.3(2) . . ? C1 C4 C2 122.0(2) . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C5 C1 C4 118.9(2) . . ? C5 C1 H1A 120.5 . . ? C4 C1 H1A 120.5 . . ? C5 C3 H3A 109.5 . . ? C5 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C5 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.34 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.337 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.088 #end