Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Joshua D. Lawrence' 'Hongxiang Li' 'Thomas B. Rauchfuss' _publ_contact_author_name 'Prof T Rauchfuss' _publ_contact_author_address ; Prof T Rauchfuss Department of Chemistry University of Illinois at Urbana Champaign 600 S Mathews Avenue Urbana IL 61801 USA ; _publ_contact_author_email 'RAUCHFUZ@UIUC.EDU' _publ_section_title ; Beyond Fe-only Hydrogenases: N-Functionalized 2-Aza- 1,3-dithiolates Fe2[(SCH2)2NR](CO)x ( x = 5, 6) ; data_4a _database_code_CSD 163360 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H9 Fe2 N O5 S2' _chemical_formula_weight 399.00 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.7450(13) _cell_length_b 9.4727(11) _cell_length_c 14.1176(16) _cell_angle_alpha 90.00 _cell_angle_beta 91.324(2) _cell_angle_gamma 90.00 _cell_volume 1436.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description platy _exptl_crystal_colour red _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.845 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 2.324 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7248 _exptl_absorpt_correction_T_max 0.9990 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 11960 _diffrn_reflns_av_R_equivalents 0.0763 _diffrn_reflns_av_sigmaI/netI 0.0888 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.99 _reflns_number_total 3222 _reflns_number_gt 1918 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0201P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3222 _refine_ls_number_parameters 209 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0973 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0639 _refine_ls_wR_factor_gt 0.0548 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.914 _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 Fe1 Fe 0.91275(4) 0.22726(5) 0.61091(3) 0.03227(14) Uani 1 1 d . A . Fe2 Fe 1.06853(4) 0.31567(5) 0.73250(3) 0.03405(14) Uani 1 1 d . . . S1 S 0.86014(7) 0.32281(9) 0.75014(6) 0.0352(2) Uani 1 1 d . A . S2 S 1.04079(7) 0.08527(9) 0.69690(6) 0.0386(2) Uani 1 1 d . A . O2 O 1.0708(2) 0.1673(3) 0.44909(18) 0.0635(8) Uani 1 1 d . A . N1 N 0.9186(2) 0.0951(3) 0.8693(2) 0.0436(8) Uani 1 1 d . . . C7 C 0.9593(3) 0.0020(3) 0.7972(3) 0.0475(10) Uani 1 1 d . A . H7A H 0.8859 -0.0494 0.7713 0.057 Uiso 1 1 calc R . . H7B H 1.0158 -0.0687 0.8267 0.057 Uiso 1 1 calc R . . O1 O 0.8357(2) 0.4891(3) 0.51579(17) 0.0546(7) Uani 1 1 d . A . O4 O 1.2945(2) 0.2936(3) 0.62268(18) 0.0661(8) Uani 1 1 d . . . C2 C 1.0078(3) 0.1881(3) 0.5118(3) 0.0419(9) Uani 1 1 d . . . C6 C 0.8196(3) 0.1873(3) 0.8387(2) 0.0450(9) Uani 1 1 d . A . H6A H 0.7872 0.2359 0.8951 0.054 Uiso 1 1 calc R . . H6B H 0.7512 0.1287 0.8117 0.054 Uiso 1 1 calc R . . C1 C 0.8633(3) 0.3880(4) 0.5538(2) 0.0375(9) Uani 1 1 d . . . C4 C 1.2075(3) 0.3034(4) 0.6674(2) 0.0441(9) Uani 1 1 d . A . C5 C 1.0606(3) 0.5001(4) 0.7165(3) 0.0574(11) Uani 1 1 d . A . O5 O 1.0526(3) 0.6201(3) 0.7032(2) 0.0920(11) Uani 1 1 d . . . O3 O 0.6935(3) 0.0491(3) 0.57374(18) 0.0767(9) Uani 1 1 d . A . C3 C 0.7794(3) 0.1175(4) 0.5866(2) 0.0461(10) Uani 1 1 d . . . C8 C 1.005(2) 0.1770(19) 0.930(2) 0.037(4) Uani 0.485(12) 1 d PD A 1 H8A H 1.0681 0.1112 0.9572 0.045 Uiso 0.485(12) 1 calc PR A 1 H8B H 0.9572 0.2144 0.9842 0.045 Uiso 0.485(12) 1 calc PR A 1 C9 C 1.0708(8) 0.2961(15) 0.8867(7) 0.049(4) Uani 0.485(12) 1 d PD A 1 H9 H 1.0484 0.3876 0.9173 0.059 Uiso 0.485(12) 1 calc PR A 1 C10 C 1.1927(8) 0.2997(16) 0.8535(6) 0.048(3) Uani 0.485(12) 1 d PD A 1 H10A H 1.2410 0.2110 0.8596 0.057 Uiso 0.485(12) 1 calc PR A 1 H10B H 1.2420 0.3850 0.8695 0.057 Uiso 0.485(12) 1 calc PR A 1 C8A C 1.0326(19) 0.1542(19) 0.9168(19) 0.039(4) Uani 0.515(12) 1 d PD A 2 H8A1 H 1.0033 0.2101 0.9712 0.047 Uiso 0.515(12) 1 calc PR A 2 H8A2 H 1.0785 0.0726 0.9440 0.047 Uiso 0.515(12) 1 calc PR A 2 C9A C 1.1264(12) 0.2428(10) 0.8695(7) 0.050(3) Uani 0.515(12) 1 d PD A 2 H9A H 1.2093 0.1949 0.8680 0.060 Uiso 0.515(12) 1 calc PR A 2 C10A C 1.1380(13) 0.3880(10) 0.8652(6) 0.057(3) Uani 0.515(12) 1 d PD A 2 H10C H 1.2239 0.4259 0.8666 0.069 Uiso 0.515(12) 1 calc PR A 2 H10D H 1.0798 0.4434 0.9038 0.069 Uiso 0.515(12) 1 calc PR A 2 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 0.0320(3) 0.0321(3) 0.0326(3) 0.0009(2) -0.0021(2) -0.0018(2) Fe2 0.0317(3) 0.0373(3) 0.0330(3) 0.0038(2) -0.0033(2) -0.0067(2) S1 0.0336(5) 0.0381(5) 0.0342(5) 0.0042(4) 0.0045(4) 0.0069(4) S2 0.0321(5) 0.0340(5) 0.0498(6) 0.0030(4) 0.0026(4) 0.0044(4) O2 0.0798(19) 0.0533(17) 0.0586(19) -0.0148(15) 0.0271(15) -0.0075(15) N1 0.0340(17) 0.051(2) 0.046(2) 0.0203(16) 0.0003(15) -0.0002(15) C7 0.036(2) 0.038(2) 0.068(3) 0.023(2) -0.0017(19) 0.0006(17) O1 0.0684(18) 0.0476(17) 0.0478(17) 0.0127(14) 0.0042(13) 0.0132(14) O4 0.0388(15) 0.097(2) 0.0627(19) 0.0087(16) 0.0125(14) -0.0124(14) C2 0.052(2) 0.032(2) 0.041(2) -0.0033(18) -0.0013(18) -0.0042(17) C6 0.0353(19) 0.054(3) 0.046(2) 0.0171(19) 0.0098(16) 0.0010(18) C1 0.0352(19) 0.048(2) 0.029(2) -0.0027(18) 0.0019(16) -0.0024(17) C4 0.041(2) 0.050(2) 0.041(2) 0.0079(19) -0.0086(18) -0.0129(18) C5 0.052(2) 0.050(3) 0.070(3) 0.001(2) -0.009(2) -0.014(2) O5 0.098(2) 0.0379(18) 0.140(3) 0.0105(19) -0.014(2) -0.0160(17) O3 0.0724(19) 0.089(2) 0.067(2) 0.0344(16) -0.0315(16) -0.0473(17) C3 0.052(2) 0.051(3) 0.035(2) 0.0146(18) -0.0112(19) -0.0095(19) C8 0.025(8) 0.066(9) 0.022(8) 0.015(7) 0.014(5) 0.018(6) C9 0.042(6) 0.069(10) 0.034(6) -0.005(5) -0.021(5) -0.001(6) C10 0.041(6) 0.072(10) 0.029(5) 0.007(5) -0.017(4) -0.011(5) C8A 0.028(9) 0.061(7) 0.030(9) -0.001(6) 0.008(6) 0.008(6) C9A 0.030(6) 0.075(9) 0.043(6) 0.030(6) -0.008(5) -0.011(6) C10A 0.066(8) 0.070(7) 0.035(5) -0.006(5) -0.015(5) -0.022(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C2 1.790(4) . ? Fe1 C3 1.796(4) . ? Fe1 C1 1.797(4) . ? Fe1 S1 2.2480(9) . ? Fe1 S2 2.2579(10) . ? Fe1 Fe2 2.5132(6) . ? Fe2 C5 1.764(4) . ? Fe2 C4 1.775(4) . ? Fe2 C10A 2.115(7) . ? Fe2 C9A 2.133(9) . ? Fe2 C10 2.149(8) . ? Fe2 C9 2.185(10) . ? Fe2 S2 2.2578(10) . ? Fe2 S1 2.2596(9) . ? S1 C6 1.851(3) . ? S2 C7 1.858(3) . ? O2 C2 1.144(4) . ? N1 C7 1.423(4) . ? N1 C6 1.436(4) . ? N1 C8 1.47(3) . ? N1 C8A 1.49(3) . ? O1 C1 1.135(3) . ? O4 C4 1.145(4) . ? C5 O5 1.154(4) . ? O3 C3 1.140(3) . ? C8 C9 1.476(12) . ? C9 C10 1.401(11) . ? C8A C9A 1.482(11) . ? C9A C10A 1.383(11) . ? 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 C2 Fe1 C3 101.40(15) . . ? C2 Fe1 C1 89.60(14) . . ? C3 Fe1 C1 100.28(14) . . ? C2 Fe1 S1 157.89(11) . . ? C3 Fe1 S1 100.62(11) . . ? C1 Fe1 S1 88.48(10) . . ? C2 Fe1 S2 86.86(11) . . ? C3 Fe1 S2 103.36(11) . . ? C1 Fe1 S2 156.33(10) . . ? S1 Fe1 S2 86.11(3) . . ? C2 Fe1 Fe2 102.71(11) . . ? C3 Fe1 Fe2 147.00(10) . . ? C1 Fe1 Fe2 102.09(10) . . ? S1 Fe1 Fe2 56.33(3) . . ? S2 Fe1 Fe2 56.18(3) . . ? C5 Fe2 C4 92.17(16) . . ? C5 Fe2 C10A 78.9(3) . . ? C4 Fe2 C10A 101.3(4) . . ? C5 Fe2 C9A 116.7(3) . . ? C4 Fe2 C9A 102.5(4) . . ? C10A Fe2 C9A 38.0(3) . . ? C5 Fe2 C10 101.5(4) . . ? C4 Fe2 C10 83.9(3) . . ? C10A Fe2 C10 28.1(3) . . ? C9A Fe2 C10 25.0(3) . . ? C5 Fe2 C9 102.2(4) . . ? C4 Fe2 C9 121.3(3) . . ? C10A Fe2 C9 31.7(3) . . ? C9A Fe2 C9 21.9(3) . . ? C10 Fe2 C9 37.7(3) . . ? C5 Fe2 S2 157.44(13) . . ? C4 Fe2 S2 85.96(11) . . ? C10A Fe2 S2 123.5(2) . . ? C9A Fe2 S2 85.6(3) . . ? C10 Fe2 S2 100.7(4) . . ? C9 Fe2 S2 97.9(4) . . ? C5 Fe2 S1 86.51(12) . . ? C4 Fe2 S1 155.03(11) . . ? C10A Fe2 S1 102.9(4) . . ? C9A Fe2 S1 100.3(4) . . ? C10 Fe2 S1 120.9(2) . . ? C9 Fe2 S1 83.2(2) . . ? S2 Fe2 S1 85.84(3) . . ? C5 Fe2 Fe1 102.31(12) . . ? C4 Fe2 Fe1 100.33(11) . . ? C10A Fe2 Fe1 158.3(4) . . ? C9A Fe2 Fe1 133.4(3) . . ? C10 Fe2 Fe1 155.7(4) . . ? C9 Fe2 Fe1 130.1(2) . . ? S2 Fe2 Fe1 56.18(3) . . ? S1 Fe2 Fe1 55.89(3) . . ? C6 S1 Fe1 112.29(12) . . ? C6 S1 Fe2 107.65(10) . . ? Fe1 S1 Fe2 67.77(3) . . ? C7 S2 Fe2 107.64(12) . . ? C7 S2 Fe1 111.76(11) . . ? Fe2 S2 Fe1 67.63(3) . . ? C7 N1 C6 113.6(3) . . ? C7 N1 C8 123.1(7) . . ? C6 N1 C8 107.9(8) . . ? C7 N1 C8A 107.0(7) . . ? C6 N1 C8A 120.1(8) . . ? C8 N1 C8A 16.2(11) . . ? N1 C7 S2 116.1(2) . . ? O2 C2 Fe1 177.6(3) . . ? N1 C6 S1 116.1(2) . . ? O1 C1 Fe1 177.6(3) . . ? O4 C4 Fe2 177.5(3) . . ? O5 C5 Fe2 177.5(4) . . ? O3 C3 Fe1 178.0(4) . . ? N1 C8 C9 117.3(19) . . ? C10 C9 C8 128.3(15) . . ? C10 C9 Fe2 69.7(5) . . ? C8 C9 Fe2 119.2(13) . . ? C9 C10 Fe2 72.5(5) . . ? C9A C8A N1 124.7(19) . . ? C10A C9A C8A 130.2(16) . . ? C10A C9A Fe2 70.3(4) . . ? C8A C9A Fe2 113.9(13) . . ? C9A C10A Fe2 71.7(5) . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.379 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.081 #===END data_4f _database_code_CSD 163361 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Fe4 N2 O10 S6' _chemical_formula_weight 866.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.341(11) _cell_length_b 10.489(7) _cell_length_c 18.338(12) _cell_angle_alpha 90.00 _cell_angle_beta 110.020(12) _cell_angle_gamma 90.00 _cell_volume 3134(3) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description tabular _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.836 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 2.267 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7477 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 28546 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 28.44 _reflns_number_total 7566 _reflns_number_gt 5732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0391P)^2^+0.7693P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7566 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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 Fe1 Fe 0.20729(3) 0.81224(4) 0.18388(3) 0.02502(11) Uani 1 1 d . . . C2 C 0.2940(2) 0.7077(3) 0.2046(2) 0.0332(8) Uani 1 1 d . . . Fe2 Fe 0.11268(3) 0.74265(4) 0.05251(3) 0.02243(11) Uani 1 1 d . . . C4 C 0.13596(19) 0.8443(3) -0.0132(2) 0.0309(7) Uani 1 1 d . . . Fe3 Fe 0.67301(3) 0.70526(4) 0.20915(3) 0.02615(11) Uani 1 1 d . . . C14 C 0.48994(19) 0.8400(3) 0.1718(2) 0.0305(7) Uani 1 1 d . . . N1 N -0.02027(16) 0.7680(2) 0.15596(17) 0.0321(6) Uani 1 1 d . . . Fe4 Fe 0.53202(3) 0.74626(4) 0.11502(3) 0.02255(11) Uani 1 1 d . . . S6 S 0.45835(5) 0.82461(7) -0.00288(5) 0.02849(18) Uani 1 1 d . . . C17 C 0.67848(19) 0.8886(3) 0.05721(19) 0.0295(7) Uani 1 1 d . . . H17A H 0.6655 0.9723 0.0310 0.035 Uiso 1 1 calc R . . H17B H 0.7390 0.8828 0.0804 0.035 Uiso 1 1 calc R . . O3 O 0.22345(17) 0.8655(3) 0.34623(15) 0.0502(7) Uani 1 1 d . . . S4 S 0.62044(5) 0.60299(7) 0.09325(5) 0.02603(17) Uani 1 1 d . . . S1 S 0.12572(5) 0.63676(7) 0.16350(5) 0.02640(17) Uani 1 1 d . . . N2 N 0.65193(16) 0.7929(2) -0.00056(16) 0.0291(6) Uani 1 1 d . . . S5 S 0.63649(5) 0.88824(7) 0.13810(5) 0.02526(17) Uani 1 1 d . . . C13 C 0.7817(2) 0.6860(3) 0.22734(19) 0.0310(7) Uani 1 1 d . . . S3 S -0.01572(5) 0.67021(7) -0.01347(5) 0.03067(19) Uani 1 1 d . . . C5 C 0.1672(2) 0.6171(3) 0.0270(2) 0.0336(8) Uani 1 1 d . . . S2 S 0.09163(5) 0.91953(7) 0.11541(5) 0.02624(17) Uani 1 1 d . . . O5 O 0.20467(17) 0.5390(2) 0.01113(16) 0.0505(7) Uani 1 1 d . . . O15 O 0.44000(16) 0.5212(2) 0.13114(17) 0.0492(7) Uani 1 1 d . . . O12 O 0.64141(17) 0.4690(2) 0.27982(16) 0.0499(7) Uani 1 1 d . . . O13 O 0.84985(15) 0.6697(2) 0.23838(16) 0.0474(7) Uani 1 1 d . . . O4 O 0.15440(17) 0.9105(2) -0.05522(16) 0.0485(7) Uani 1 1 d . . . O14 O 0.46499(16) 0.8983(2) 0.21251(15) 0.0454(6) Uani 1 1 d . . . C10 C -0.0408(2) 0.7074(4) -0.1149(2) 0.0443(9) Uani 1 1 d . . . H10A H -0.0957 0.6748 -0.1440 0.066 Uiso 1 1 calc R . . H10B H -0.0005 0.6676 -0.1343 0.066 Uiso 1 1 calc R . . H10C H -0.0398 0.8001 -0.1215 0.066 Uiso 1 1 calc R . . C3 C 0.2176(2) 0.8481(3) 0.2830(2) 0.0331(8) Uani 1 1 d . . . C15 C 0.4742(2) 0.6113(3) 0.1236(2) 0.0316(7) Uani 1 1 d . . . C11 C 0.6728(2) 0.8002(3) 0.2900(2) 0.0388(8) Uani 1 1 d . . . O2 O 0.34961(15) 0.6421(2) 0.21950(16) 0.0462(6) Uani 1 1 d . . . C16 C 0.67137(19) 0.6654(3) 0.02572(19) 0.0276(7) Uani 1 1 d . . . H16A H 0.7315 0.6594 0.0521 0.033 Uiso 1 1 calc R . . H16B H 0.6567 0.6089 -0.0203 0.033 Uiso 1 1 calc R . . C12 C 0.6546(2) 0.5609(3) 0.2530(2) 0.0356(8) Uani 1 1 d . . . C19 C 0.4980(2) 0.7565(3) -0.0743(2) 0.0391(8) Uani 1 1 d . . . H19A H 0.5046 0.6633 -0.0659 0.047 Uiso 1 1 calc R . . H19B H 0.4576 0.7708 -0.1269 0.047 Uiso 1 1 calc R . . C1 C 0.2607(2) 0.9430(3) 0.1590(2) 0.0384(8) Uani 1 1 d . . . O1 O 0.29209(17) 1.0261(3) 0.14030(18) 0.0589(8) Uani 1 1 d . . . C7 C 0.0144(2) 0.8926(3) 0.1639(2) 0.0328(8) Uani 1 1 d . . . H7A H 0.0407 0.9110 0.2199 0.039 Uiso 1 1 calc R . . H7B H -0.0307 0.9547 0.1428 0.039 Uiso 1 1 calc R . . C8 C -0.0925(2) 0.7420(3) 0.0896(2) 0.0370(8) Uani 1 1 d . . . H8A H -0.1385 0.7912 0.0960 0.044 Uiso 1 1 calc R . . H8B H -0.1060 0.6505 0.0911 0.044 Uiso 1 1 calc R . . C6 C 0.0351(2) 0.6688(3) 0.1940(2) 0.0335(8) Uani 1 1 d . . . H6A H 0.0031 0.5888 0.1873 0.040 Uiso 1 1 calc R . . H6B H 0.0560 0.6884 0.2502 0.040 Uiso 1 1 calc R . . O11 O 0.6715(2) 0.8616(3) 0.34128(16) 0.0632(9) Uani 1 1 d . . . C18 C 0.5801(2) 0.8138(3) -0.0703(2) 0.0386(8) Uani 1 1 d . . . H18A H 0.5935 0.7807 -0.1151 0.046 Uiso 1 1 calc R . . H18B H 0.5724 0.9070 -0.0776 0.046 Uiso 1 1 calc R . . C9 C -0.0900(2) 0.7706(3) 0.0094(2) 0.0367(8) Uani 1 1 d . . . H9A H -0.0753 0.8613 0.0067 0.044 Uiso 1 1 calc R . . H9B H -0.1451 0.7565 -0.0297 0.044 Uiso 1 1 calc R . . C20 C 0.3572(2) 0.7526(3) -0.0366(2) 0.0430(9) Uani 1 1 d . . . H20A H 0.3256 0.7868 -0.0879 0.065 Uiso 1 1 calc R . . H20B H 0.3288 0.7721 -0.0001 0.065 Uiso 1 1 calc R . . H20C H 0.3625 0.6600 -0.0402 0.065 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 0.0236(2) 0.0256(2) 0.0253(3) -0.00094(18) 0.00773(19) 0.00001(17) C2 0.0311(18) 0.0324(16) 0.038(2) -0.0046(14) 0.0136(16) -0.0031(14) Fe2 0.0240(2) 0.0212(2) 0.0227(2) 0.00091(16) 0.00873(19) 0.00321(16) C4 0.0295(17) 0.0290(16) 0.036(2) 0.0001(14) 0.0131(15) 0.0083(13) Fe3 0.0257(2) 0.0278(2) 0.0227(3) 0.00186(18) 0.00539(19) 0.00194(18) C14 0.0285(17) 0.0292(16) 0.034(2) -0.0031(14) 0.0115(15) -0.0017(13) N1 0.0287(15) 0.0347(14) 0.0363(18) 0.0021(12) 0.0152(13) 0.0003(11) Fe4 0.0217(2) 0.0221(2) 0.0247(3) -0.00387(17) 0.00911(19) 0.00012(16) S6 0.0235(4) 0.0288(4) 0.0294(5) -0.0031(3) 0.0042(3) 0.0031(3) C17 0.0282(17) 0.0274(15) 0.036(2) 0.0024(13) 0.0156(15) 0.0011(12) O3 0.0616(18) 0.0591(16) 0.0309(16) -0.0087(12) 0.0171(14) 0.0032(14) S4 0.0255(4) 0.0212(3) 0.0326(5) -0.0026(3) 0.0114(3) 0.0015(3) S1 0.0274(4) 0.0232(3) 0.0286(4) 0.0044(3) 0.0094(3) 0.0022(3) N2 0.0312(15) 0.0330(13) 0.0257(15) 0.0022(11) 0.0130(12) 0.0058(11) S5 0.0259(4) 0.0218(3) 0.0278(4) -0.0032(3) 0.0089(3) -0.0010(3) C13 0.0319(18) 0.0351(17) 0.0206(18) 0.0058(13) 0.0019(14) 0.0014(14) S3 0.0291(4) 0.0240(4) 0.0342(5) -0.0012(3) 0.0049(4) 0.0009(3) C5 0.040(2) 0.0299(16) 0.033(2) 0.0044(14) 0.0144(16) 0.0073(14) S2 0.0284(4) 0.0206(3) 0.0323(5) 0.0005(3) 0.0137(4) 0.0022(3) O5 0.0639(18) 0.0484(15) 0.0451(17) 0.0025(12) 0.0262(15) 0.0267(14) O15 0.0567(17) 0.0379(13) 0.067(2) -0.0144(13) 0.0400(15) -0.0174(12) O12 0.0574(17) 0.0466(15) 0.0501(18) 0.0178(13) 0.0240(14) 0.0007(13) O13 0.0300(14) 0.0608(17) 0.0504(18) 0.0152(13) 0.0124(13) 0.0020(12) O4 0.0578(17) 0.0494(15) 0.0464(17) 0.0160(13) 0.0285(14) 0.0038(13) O14 0.0517(16) 0.0466(14) 0.0457(17) -0.0116(12) 0.0266(14) 0.0059(12) C10 0.041(2) 0.053(2) 0.030(2) -0.0094(16) -0.0001(17) -0.0017(17) C3 0.0294(17) 0.0326(17) 0.036(2) -0.0020(14) 0.0091(16) 0.0001(13) C15 0.0300(17) 0.0333(17) 0.036(2) -0.0103(14) 0.0172(16) -0.0007(14) C11 0.043(2) 0.047(2) 0.0202(19) 0.0035(15) 0.0031(16) 0.0041(16) O2 0.0341(14) 0.0481(15) 0.0539(18) -0.0045(13) 0.0119(13) 0.0111(12) C16 0.0262(16) 0.0318(16) 0.0281(18) -0.0058(13) 0.0134(14) 0.0017(13) C12 0.0293(18) 0.0394(18) 0.040(2) 0.0050(16) 0.0146(16) 0.0057(14) C19 0.035(2) 0.051(2) 0.027(2) -0.0073(16) 0.0060(16) 0.0090(16) C1 0.0308(19) 0.0419(19) 0.041(2) 0.0016(16) 0.0106(17) -0.0045(15) O1 0.0497(17) 0.0552(17) 0.069(2) 0.0150(15) 0.0171(15) -0.0155(14) C7 0.0314(18) 0.0319(16) 0.041(2) -0.0029(14) 0.0196(16) 0.0038(13) C8 0.0262(17) 0.0430(19) 0.043(2) 0.0023(16) 0.0136(16) -0.0011(14) C6 0.0345(18) 0.0403(18) 0.0297(19) 0.0083(14) 0.0163(16) 0.0004(14) O11 0.087(2) 0.0704(19) 0.0269(16) -0.0093(14) 0.0126(15) 0.0157(17) C18 0.040(2) 0.055(2) 0.0237(19) 0.0066(16) 0.0142(16) 0.0092(17) C9 0.0240(17) 0.0345(17) 0.050(2) 0.0022(15) 0.0098(16) 0.0039(13) C20 0.0246(18) 0.0398(19) 0.056(3) -0.0081(17) 0.0029(17) -0.0003(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 C2 1.793(4) . ? Fe1 C1 1.799(4) . ? Fe1 C3 1.804(4) . ? Fe1 S2 2.2675(13) . ? Fe1 S1 2.2729(14) . ? Fe1 Fe2 2.5144(14) . ? C2 O2 1.139(4) . ? Fe2 C4 1.757(3) . ? Fe2 C5 1.774(3) . ? Fe2 S1 2.2609(15) . ? Fe2 S3 2.2703(15) . ? Fe2 S2 2.2789(14) . ? C4 O4 1.160(4) . ? Fe3 C11 1.787(4) . ? Fe3 C12 1.793(4) . ? Fe3 C13 1.810(4) . ? Fe3 S4 2.2743(15) . ? Fe3 S5 2.2841(14) . ? Fe3 Fe4 2.5005(14) . ? C14 O14 1.157(4) . ? C14 Fe4 1.762(3) . ? N1 C6 1.425(4) . ? N1 C7 1.425(4) . ? N1 C8 1.443(4) . ? Fe4 C15 1.772(3) . ? Fe4 S6 2.2563(14) . ? Fe4 S5 2.2702(14) . ? Fe4 S4 2.2776(13) . ? S6 C20 1.813(4) . ? S6 C19 1.821(4) . ? C17 N2 1.417(4) . ? C17 S5 1.863(3) . ? O3 C3 1.144(4) . ? S4 C16 1.868(3) . ? S1 C6 1.870(3) . ? N2 C16 1.422(4) . ? N2 C18 1.464(4) . ? C13 O13 1.141(4) . ? S3 C10 1.802(4) . ? S3 C9 1.820(3) . ? C5 O5 1.144(4) . ? S2 C7 1.865(3) . ? O15 C15 1.150(4) . ? O12 C12 1.141(4) . ? C11 O11 1.146(4) . ? C19 C18 1.523(5) . ? C1 O1 1.141(4) . ? C8 C9 1.517(5) . ? 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 C2 Fe1 C1 93.05(16) . . ? C2 Fe1 C3 97.30(16) . . ? C1 Fe1 C3 102.38(16) . . ? C2 Fe1 S2 159.93(12) . . ? C1 Fe1 S2 85.15(12) . . ? C3 Fe1 S2 102.62(11) . . ? C2 Fe1 S1 88.23(12) . . ? C1 Fe1 S1 157.08(12) . . ? C3 Fe1 S1 100.15(11) . . ? S2 Fe1 S1 85.87(5) . . ? C2 Fe1 Fe2 104.49(12) . . ? C1 Fe1 Fe2 101.64(12) . . ? C3 Fe1 Fe2 146.42(11) . . ? S2 Fe1 Fe2 56.64(4) . . ? S1 Fe1 Fe2 56.09(3) . . ? O2 C2 Fe1 178.4(3) . . ? C4 Fe2 C5 90.07(15) . . ? C4 Fe2 S1 160.09(11) . . ? C5 Fe2 S1 88.52(12) . . ? C4 Fe2 S3 104.55(12) . . ? C5 Fe2 S3 97.18(12) . . ? S1 Fe2 S3 95.34(4) . . ? C4 Fe2 S2 88.15(11) . . ? C5 Fe2 S2 158.35(12) . . ? S1 Fe2 S2 85.89(6) . . ? S3 Fe2 S2 104.15(4) . . ? C4 Fe2 Fe1 104.69(12) . . ? C5 Fe2 Fe1 103.65(12) . . ? S1 Fe2 Fe1 56.55(4) . . ? S3 Fe2 Fe1 143.80(3) . . ? S2 Fe2 Fe1 56.21(3) . . ? O4 C4 Fe2 177.5(3) . . ? C11 Fe3 C12 92.73(17) . . ? C11 Fe3 C13 101.97(16) . . ? C12 Fe3 C13 99.02(14) . . ? C11 Fe3 S4 157.53(12) . . ? C12 Fe3 S4 86.83(13) . . ? C13 Fe3 S4 100.28(11) . . ? C11 Fe3 S5 85.75(12) . . ? C12 Fe3 S5 155.23(11) . . ? C13 Fe3 S5 105.48(10) . . ? S4 Fe3 S5 85.36(5) . . ? C11 Fe3 Fe4 101.39(12) . . ? C12 Fe3 Fe4 99.95(11) . . ? C13 Fe3 Fe4 148.99(11) . . ? S4 Fe3 Fe4 56.74(3) . . ? S5 Fe3 Fe4 56.43(3) . . ? O14 C14 Fe4 176.5(3) . . ? C6 N1 C7 115.4(3) . . ? C6 N1 C8 121.3(3) . . ? C7 N1 C8 118.3(3) . . ? C14 Fe4 C15 91.80(15) . . ? C14 Fe4 S6 98.64(12) . . ? C15 Fe4 S6 102.96(12) . . ? C14 Fe4 S5 89.39(11) . . ? C15 Fe4 S5 161.23(12) . . ? S6 Fe4 S5 95.37(4) . . ? C14 Fe4 S4 155.73(11) . . ? C15 Fe4 S4 85.64(11) . . ? S6 Fe4 S4 105.46(5) . . ? S5 Fe4 S4 85.60(6) . . ? C14 Fe4 Fe3 101.11(12) . . ? C15 Fe4 Fe3 104.50(12) . . ? S6 Fe4 Fe3 145.41(3) . . ? S5 Fe4 Fe3 56.97(4) . . ? S4 Fe4 Fe3 56.61(4) . . ? C20 S6 C19 98.66(17) . . ? C20 S6 Fe4 109.86(14) . . ? C19 S6 Fe4 108.50(13) . . ? N2 C17 S5 118.6(2) . . ? C16 S4 Fe3 108.97(11) . . ? C16 S4 Fe4 112.60(10) . . ? Fe3 S4 Fe4 66.64(4) . . ? C6 S1 Fe2 110.20(11) . . ? C6 S1 Fe1 110.16(12) . . ? Fe2 S1 Fe1 67.36(4) . . ? C17 N2 C16 115.7(3) . . ? C17 N2 C18 120.6(3) . . ? C16 N2 C18 117.9(3) . . ? C17 S5 Fe4 110.93(11) . . ? C17 S5 Fe3 110.38(10) . . ? Fe4 S5 Fe3 66.60(4) . . ? O13 C13 Fe3 177.8(3) . . ? C10 S3 C9 99.92(17) . . ? C10 S3 Fe2 108.89(13) . . ? C9 S3 Fe2 109.02(12) . . ? O5 C5 Fe2 177.6(3) . . ? C7 S2 Fe1 107.69(12) . . ? C7 S2 Fe2 112.54(10) . . ? Fe1 S2 Fe2 67.15(4) . . ? O3 C3 Fe1 177.0(3) . . ? O15 C15 Fe4 176.9(3) . . ? O11 C11 Fe3 179.1(4) . . ? N2 C16 S4 116.3(2) . . ? O12 C12 Fe3 178.7(4) . . ? C18 C19 S6 112.8(2) . . ? O1 C1 Fe1 177.2(4) . . ? N1 C7 S2 115.9(2) . . ? N1 C8 C9 118.4(3) . . ? N1 C6 S1 118.7(2) . . ? N2 C18 C19 119.0(3) . . ? C8 C9 S3 111.5(2) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 28.44 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.456 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.110