# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Chris Adams' _publ_contact_author_address ; Cantock's Close Bristol BS8 1TS ; _publ_contact_author_email chcja@bris.ac.uk loop_ _publ_author_name C.Adams J.Real R.Waddington data_1-2trichloroethene _database_code_depnum_ccdc_archive 'CCDC 771541' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H18 Cl6 Fe1 N6 S2' _chemical_formula_weight 747.14 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.508(4) _cell_length_b 11.5522(18) _cell_length_c 12.3631(19) _cell_angle_alpha 90.00 _cell_angle_beta 103.304(9) _cell_angle_gamma 90.00 _cell_volume 3128.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8868 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 30.52 _exptl_crystal_description Lath _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 1.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7607 _exptl_absorpt_correction_T_max 0.9772 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28805 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 30.60 _reflns_number_total 4569 _reflns_number_gt 3815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0442P)^2^+7.1352P] 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 4569 _refine_ls_number_parameters 234 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.044 _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 0.0000 0.28377(3) 0.2500 0.01008(9) Uani 1 2 d S . . N1 N 0.03210(7) 0.28145(12) 0.10209(12) 0.0152(3) Uani 1 1 d . . . C1 C 0.07170(9) 0.30361(14) 0.05891(14) 0.0155(3) Uani 1 1 d . . . S1 S 0.12672(3) 0.33588(5) -0.00080(5) 0.02992(13) Uani 1 1 d . . . N3 N -0.09573(7) 0.27541(12) 0.15361(12) 0.0140(3) Uani 1 1 d . . . C3 C -0.11628(9) 0.33400(16) 0.05897(15) 0.0195(4) Uani 1 1 d . . . H3A H -0.0887 0.3834 0.0333 0.023 Uiso 1 1 calc R . . C4 C -0.17571(9) 0.32625(18) -0.00351(16) 0.0222(4) Uani 1 1 d . . . H4A H -0.1878 0.3693 -0.0705 0.027 Uiso 1 1 calc R . . C5 C -0.21778(8) 0.25547(14) 0.03166(14) 0.0132(3) Uani 1 1 d . . . C6 C -0.19617(9) 0.19536(17) 0.13079(16) 0.0218(4) Uani 1 1 d . . . H6A H -0.2228 0.1461 0.1591 0.026 Uiso 1 1 calc R . . C7 C -0.13609(9) 0.20740(16) 0.18772(16) 0.0210(4) Uani 1 1 d . . . H7A H -0.1226 0.1651 0.2548 0.025 Uiso 1 1 calc R . . N5 N 0.0000 0.09102(16) 0.2500 0.0130(4) Uani 1 2 d S . . C13 C -0.01267(9) 0.03072(14) 0.15469(14) 0.0173(3) Uani 1 1 d . . . H13A H -0.0221 0.0723 0.0866 0.021 Uiso 1 1 calc R . . C14 C -0.01263(9) -0.08922(14) 0.15065(14) 0.0180(3) Uani 1 1 d . . . H14A H -0.0211 -0.1285 0.0813 0.022 Uiso 1 1 calc R . . C15 C 0.0000 -0.15122(19) 0.2500 0.0134(4) Uani 1 2 d S . . N6 N 0.0000 -0.52210(16) 0.2500 0.0133(4) Uani 1 2 d S . . C18 C -0.03060(9) -0.46107(14) 0.31210(15) 0.0174(3) Uani 1 1 d . . . H18A H -0.0530 -0.5023 0.3561 0.021 Uiso 1 1 calc R . . C21 C -0.03133(9) -0.34126(14) 0.31542(15) 0.0179(3) Uani 1 1 d . . . H21A H -0.0530 -0.3021 0.3619 0.021 Uiso 1 1 calc R . . C22 C 0.0000 -0.27901(19) 0.2500 0.0135(4) Uani 1 2 d S . . C100 C -0.29769(16) 0.5677(3) -0.2891(3) 0.0360(7) Uani 0.839(3) 1 d P A 1 C101 C -0.23963(15) 0.5575(2) -0.2475(2) 0.0322(6) Uani 0.839(3) 1 d P A 1 H10A H -0.2222 0.6017 -0.1832 0.039 Uiso 0.839(3) 1 calc PR A 1 Cl1 Cl -0.34098(8) 0.65317(19) -0.2240(2) 0.0653(6) Uani 0.839(3) 1 d P A 1 Cl2 Cl -0.33745(8) 0.49604(11) -0.40538(8) 0.0635(4) Uani 0.839(3) 1 d P A 1 Cl3 Cl -0.19245(4) 0.46981(7) -0.30086(8) 0.0479(3) Uani 0.839(3) 1 d P A 1 Cl3' Cl -0.2437(4) 0.4399(5) -0.3918(7) 0.082(3) Uani 0.161(3) 1 d P A 2 Cl2' Cl -0.3717(4) 0.5180(7) -0.4217(8) 0.089(3) Uani 0.161(3) 1 d P A 2 Cl1' Cl -0.3209(7) 0.6667(11) -0.1960(14) 0.101(5) Uani 0.161(3) 1 d P A 2 C200 C -0.2898(9) 0.5231(13) -0.3384(14) 0.037(3) Uani 0.161(3) 1 d PU A 2 C201 C -0.2712(7) 0.5910(11) -0.2365(13) 0.024(3) Uani 0.161(3) 1 d PU A 2 H201 H -0.2300 0.5899 -0.1951 0.028 Uiso 0.161(3) 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 0.00981(18) 0.00865(14) 0.01106(15) 0.000 0.00091(12) 0.000 N1 0.0178(8) 0.0134(6) 0.0138(6) -0.0012(5) 0.0025(6) 0.0000(5) C1 0.0181(9) 0.0134(7) 0.0138(7) -0.0020(5) 0.0014(7) 0.0002(6) S1 0.0233(3) 0.0423(3) 0.0277(3) 0.0006(2) 0.0130(2) -0.0072(2) N3 0.0126(7) 0.0126(6) 0.0160(6) 0.0010(5) 0.0017(5) 0.0005(5) C3 0.0133(9) 0.0245(9) 0.0194(8) 0.0069(7) 0.0014(7) -0.0039(7) C4 0.0153(10) 0.0298(9) 0.0194(8) 0.0112(7) -0.0004(7) -0.0040(7) C5 0.0110(9) 0.0140(7) 0.0137(7) -0.0004(5) 0.0007(7) -0.0003(6) C6 0.0147(9) 0.0237(9) 0.0238(9) 0.0103(7) -0.0021(7) -0.0054(7) C7 0.0160(9) 0.0219(8) 0.0217(8) 0.0100(7) -0.0024(7) -0.0046(7) N5 0.0140(10) 0.0108(8) 0.0135(8) 0.000 0.0019(8) 0.000 C13 0.0251(10) 0.0113(7) 0.0139(7) 0.0013(5) 0.0015(7) -0.0015(6) C14 0.0278(10) 0.0102(7) 0.0150(7) -0.0012(5) 0.0032(7) -0.0022(6) C15 0.0160(12) 0.0090(9) 0.0162(10) 0.000 0.0054(9) 0.000 N6 0.0133(10) 0.0104(8) 0.0157(9) 0.000 0.0025(8) 0.000 C18 0.0209(10) 0.0117(7) 0.0220(8) 0.0017(6) 0.0098(7) 0.0006(6) C21 0.0237(10) 0.0108(7) 0.0214(8) 0.0006(6) 0.0100(7) 0.0015(6) C22 0.0165(12) 0.0092(9) 0.0140(10) 0.000 0.0015(9) 0.000 C100 0.0337(18) 0.0296(14) 0.0448(18) 0.0148(14) 0.0092(16) -0.0015(13) C101 0.0355(17) 0.0267(12) 0.0373(14) 0.0083(10) 0.0141(13) 0.0005(12) Cl1 0.0416(7) 0.0531(9) 0.1106(14) 0.0187(9) 0.0369(7) 0.0181(6) Cl2 0.0739(9) 0.0695(7) 0.0372(4) 0.0147(4) -0.0075(5) -0.0437(7) Cl3 0.0537(6) 0.0455(4) 0.0556(5) 0.0157(4) 0.0353(5) 0.0189(4) Cl3' 0.102(6) 0.053(3) 0.117(6) 0.000(3) 0.078(5) 0.012(3) Cl2' 0.057(5) 0.075(4) 0.122(7) 0.048(4) -0.008(4) -0.026(4) Cl1' 0.138(13) 0.045(4) 0.149(11) -0.031(5) 0.095(10) 0.013(6) C200 0.062(8) 0.022(5) 0.037(6) -0.002(5) 0.034(6) -0.010(5) C201 0.007(6) 0.023(5) 0.036(6) -0.003(5) -0.003(5) 0.003(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 Fe1 N1 2.1153(15) . ? Fe1 N1 2.1154(15) 2 ? Fe1 N3 2.2114(16) 2 ? Fe1 N3 2.2115(16) . ? Fe1 N5 2.2267(19) . ? Fe1 N6 2.2427(19) 1_565 ? N1 C1 1.168(2) . ? C1 S1 1.6244(19) . ? N3 C3 1.339(2) . ? N3 C7 1.340(2) . ? C3 C4 1.385(3) . ? C4 C5 1.394(2) . ? C5 C6 1.395(2) . ? C5 C5 1.486(3) 7_455 ? C6 C7 1.380(3) . ? N5 C13 1.3418(19) . ? N5 C13 1.3418(19) 2 ? C13 C14 1.386(2) . ? C14 C15 1.393(2) . ? C15 C14 1.393(2) 2 ? C15 C22 1.476(3) . ? N6 C18 1.343(2) 2 ? N6 C18 1.343(2) . ? N6 Fe1 2.2426(19) 1_545 ? C18 C21 1.385(2) . ? C21 C22 1.390(2) . ? C22 C21 1.390(2) 2 ? C100 C101 1.295(5) . ? C100 Cl1 1.712(4) . ? C100 Cl2 1.721(4) . ? C101 Cl3 1.706(3) . ? Cl3' C200 1.658(18) . ? Cl2' C200 1.89(2) . ? Cl1' C201 1.589(18) . ? C200 C201 1.46(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 178.55(8) . 2 ? N1 Fe1 N3 88.91(6) . 2 ? N1 Fe1 N3 91.03(6) 2 2 ? N1 Fe1 N3 91.02(6) . . ? N1 Fe1 N3 88.91(6) 2 . ? N3 Fe1 N3 174.99(7) 2 . ? N1 Fe1 N5 89.28(4) . . ? N1 Fe1 N5 89.28(4) 2 . ? N3 Fe1 N5 87.50(4) 2 . ? N3 Fe1 N5 87.50(4) . . ? N1 Fe1 N6 90.73(4) . 1_565 ? N1 Fe1 N6 90.72(4) 2 1_565 ? N3 Fe1 N6 92.50(4) 2 1_565 ? N3 Fe1 N6 92.50(4) . 1_565 ? N5 Fe1 N6 180.0 . 1_565 ? C1 N1 Fe1 147.22(14) . . ? N1 C1 S1 179.39(16) . . ? C3 N3 C7 116.65(16) . . ? C3 N3 Fe1 123.14(12) . . ? C7 N3 Fe1 120.19(12) . . ? N3 C3 C4 123.35(17) . . ? C3 C4 C5 120.14(16) . . ? C4 C5 C6 116.18(16) . . ? C4 C5 C5 122.42(19) . 7_455 ? C6 C5 C5 121.40(19) . 7_455 ? C7 C6 C5 120.03(17) . . ? N3 C7 C6 123.64(17) . . ? C13 N5 C13 117.5(2) . 2 ? C13 N5 Fe1 121.28(10) . . ? C13 N5 Fe1 121.27(10) 2 . ? N5 C13 C14 123.28(16) . . ? C13 C14 C15 118.92(16) . . ? C14 C15 C14 118.1(2) 2 . ? C14 C15 C22 120.93(10) 2 . ? C14 C15 C22 120.93(10) . . ? C18 N6 C18 116.7(2) 2 . ? C18 N6 Fe1 121.66(10) 2 1_545 ? C18 N6 Fe1 121.66(10) . 1_545 ? N6 C18 C21 123.55(17) . . ? C18 C21 C22 119.26(17) . . ? C21 C22 C21 117.7(2) 2 . ? C21 C22 C15 121.16(10) 2 . ? C21 C22 C15 121.16(10) . . ? C101 C100 Cl1 119.9(3) . . ? C101 C100 Cl2 124.8(3) . . ? Cl1 C100 Cl2 115.3(2) . . ? C100 C101 Cl3 124.2(3) . . ? C201 C200 Cl3' 124.9(14) . . ? C201 C200 Cl2' 122.4(13) . . ? Cl3' C200 Cl2' 112.7(10) . . ? C200 C201 Cl1' 118.9(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Fe1 N1 C1 -115.2(2) 2 . . . ? N3 Fe1 N1 C1 -27.6(2) 2 . . . ? N3 Fe1 N1 C1 157.4(2) . . . . ? N5 Fe1 N1 C1 -115.1(2) . . . . ? N6 Fe1 N1 C1 64.9(2) 1_565 . . . ? Fe1 N1 C1 S1 -60(17) . . . . ? N1 Fe1 N3 C3 -40.04(15) . . . . ? N1 Fe1 N3 C3 141.41(15) 2 . . . ? N3 Fe1 N3 C3 -129.27(14) 2 . . . ? N5 Fe1 N3 C3 -129.27(14) . . . . ? N6 Fe1 N3 C3 50.74(14) 1_565 . . . ? N1 Fe1 N3 C7 138.43(14) . . . . ? N1 Fe1 N3 C7 -40.12(14) 2 . . . ? N3 Fe1 N3 C7 49.20(14) 2 . . . ? N5 Fe1 N3 C7 49.20(14) . . . . ? N6 Fe1 N3 C7 -130.80(14) 1_565 . . . ? C7 N3 C3 C4 -0.6(3) . . . . ? Fe1 N3 C3 C4 177.91(15) . . . . ? N3 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C3 C4 C5 C5 179.6(2) . . . 7_455 ? C4 C5 C6 C7 -0.4(3) . . . . ? C5 C5 C6 C7 -179.9(2) 7_455 . . . ? C3 N3 C7 C6 0.2(3) . . . . ? Fe1 N3 C7 C6 -178.38(16) . . . . ? C5 C6 C7 N3 0.3(3) . . . . ? N1 Fe1 N5 C13 -33.42(11) . . . . ? N1 Fe1 N5 C13 146.58(11) 2 . . . ? N3 Fe1 N5 C13 -122.36(11) 2 . . . ? N3 Fe1 N5 C13 57.64(11) . . . . ? N6 Fe1 N5 C13 105.2(9) 1_565 . . . ? N1 Fe1 N5 C13 146.58(11) . . . 2 ? N1 Fe1 N5 C13 -33.42(11) 2 . . 2 ? N3 Fe1 N5 C13 57.64(11) 2 . . 2 ? N3 Fe1 N5 C13 -122.36(11) . . . 2 ? N6 Fe1 N5 C13 -74.8(9) 1_565 . . 2 ? C13 N5 C13 C14 -0.64(14) 2 . . . ? Fe1 N5 C13 C14 179.36(14) . . . . ? N5 C13 C14 C15 1.3(3) . . . . ? C13 C14 C15 C14 -0.59(13) . . . 2 ? C13 C14 C15 C22 179.41(13) . . . . ? C18 N6 C18 C21 -0.66(14) 2 . . . ? Fe1 N6 C18 C21 179.34(14) 1_545 . . . ? N6 C18 C21 C22 1.3(3) . . . . ? C18 C21 C22 C21 -0.61(13) . . . 2 ? C18 C21 C22 C15 179.40(13) . . . . ? C14 C15 C22 C21 -131.36(14) 2 . . 2 ? C14 C15 C22 C21 48.64(14) . . . 2 ? C14 C15 C22 C21 48.64(14) 2 . . . ? C14 C15 C22 C21 -131.37(14) . . . . ? Cl1 C100 C101 Cl3 176.76(17) . . . . ? Cl2 C100 C101 Cl3 -0.5(4) . . . . ? Cl3' C200 C201 Cl1' 180.0(11) . . . . ? Cl2' C200 C201 Cl1' -2.1(18) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 1.183 _refine_diff_density_min -0.639 _refine_diff_density_rms 0.077 #===END data_1-2toluene _database_code_depnum_ccdc_archive 'CCDC 771542' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H32 Fe N6 S2' _chemical_formula_weight 668.65 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.3329(11) _cell_length_b 11.5783(5) _cell_length_c 12.9964(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.347(3) _cell_angle_gamma 90.00 _cell_volume 3167.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3311 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.16 _exptl_crystal_description Prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.065 _exptl_crystal_size_min 0.049 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.645 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.74 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13856 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.63 _reflns_number_total 3662 _reflns_number_gt 2756 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0762P)^2^+36.8617P] 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 3662 _refine_ls_number_parameters 248 _refine_ls_number_restraints 99 _refine_ls_R_factor_all 0.1053 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.2056 _refine_ls_wR_factor_gt 0.1861 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.071 _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 0.0000 0.28016(7) 0.2500 0.0175(2) Uani 1 2 d S . . N1 N 0.03851(17) 0.2757(3) 0.1107(3) 0.0212(7) Uani 1 1 d . . . C1 C 0.0734(2) 0.2977(4) 0.0533(3) 0.0228(9) Uani 1 1 d . . . S1 S 0.12106(7) 0.32912(17) -0.02800(12) 0.0493(5) Uani 1 1 d . . . N3 N -0.09733(16) 0.2758(3) 0.1574(3) 0.0201(7) Uani 1 1 d . . . C3 C -0.1133(2) 0.3375(4) 0.0699(4) 0.0286(10) Uani 1 1 d . . . H3A H -0.0826 0.3888 0.0501 0.034 Uiso 1 1 calc R . . C4 C -0.1720(2) 0.3307(4) 0.0068(4) 0.0277(10) Uani 1 1 d . . . H4A H -0.1808 0.3768 -0.0544 0.033 Uiso 1 1 calc R . . C5 C -0.2184(2) 0.2560(4) 0.0330(3) 0.0203(9) Uani 1 1 d . . . C6 C -0.2014(2) 0.1924(4) 0.1239(4) 0.0290(10) Uani 1 1 d . . . H6A H -0.2308 0.1397 0.1455 0.035 Uiso 1 1 calc R . . C7 C -0.1417(2) 0.2054(4) 0.1832(4) 0.0265(10) Uani 1 1 d . . . H7A H -0.1318 0.1618 0.2457 0.032 Uiso 1 1 calc R . . N5 N 0.0000 0.0872(4) 0.2500 0.0263(12) Uani 1 2 d S . . C13 C -0.0112(3) 0.0274(4) 0.1615(4) 0.0332(11) Uani 1 1 d . . . H13A H -0.0192 0.0687 0.0976 0.040 Uiso 1 1 calc R . . C14 C -0.0116(3) -0.0923(4) 0.1580(4) 0.0313(11) Uani 1 1 d . . . H14A H -0.0199 -0.1314 0.0929 0.038 Uiso 1 1 calc R . . C15 C 0.0000 -0.1544(5) 0.2500 0.0249(13) Uani 1 2 d S . . N6 N 0.0000 -0.5256(4) 0.2500 0.0176(10) Uani 1 2 d S . . C18 C -0.0323(2) -0.4645(4) 0.3117(4) 0.0238(9) Uani 1 1 d . . . H18A H -0.0561 -0.5054 0.3557 0.029 Uiso 1 1 calc R . . C21 C -0.0330(2) -0.3450(4) 0.3150(4) 0.0252(9) Uani 1 1 d . . . H21A H -0.0559 -0.3059 0.3614 0.030 Uiso 1 1 calc R . . C22 C 0.0000 -0.2829(5) 0.2500 0.0224(12) Uani 1 2 d S . . C100 C -0.2791(4) -0.0085(9) 0.3062(9) 0.037(4) Uani 0.425(13) 1 d PGDU A 1 H10A H -0.3146 0.0309 0.3250 0.044 Uiso 0.425(13) 1 calc PR A 1 C101 C -0.2855(4) -0.0701(10) 0.2132(7) 0.022(3) Uani 0.425(13) 1 d PGDU A 1 H10B H -0.3255 -0.0727 0.1686 0.027 Uiso 0.425(13) 1 calc PR A 1 C102 C -0.2336(5) -0.1278(9) 0.1856(6) 0.030(3) Uani 0.425(13) 1 d PGDU A 1 H10C H -0.2380 -0.1698 0.1221 0.036 Uiso 0.425(13) 1 calc PR A 1 C103 C -0.1752(4) -0.1239(10) 0.2509(8) 0.052(4) Uani 0.425(13) 1 d PGDU A 1 H10D H -0.1397 -0.1634 0.2320 0.063 Uiso 0.425(13) 1 calc PR A 1 C104 C -0.1687(4) -0.0624(10) 0.3439(7) 0.029(3) Uani 0.425(13) 1 d PGDU A 1 H10E H -0.1288 -0.0598 0.3885 0.035 Uiso 0.425(13) 1 calc PR A 1 C105 C -0.2206(5) -0.0047(10) 0.3715(7) 0.057(5) Uani 0.425(13) 1 d PGDU A 1 C106 C -0.2006(10) 0.0553(17) 0.4629(14) 0.081(6) Uani 0.425(13) 1 d PDU A 1 H10F H -0.1548 0.0696 0.4703 0.121 Uiso 0.425(13) 1 calc PR A 1 H10G H -0.2096 0.0097 0.5223 0.121 Uiso 0.425(13) 1 calc PR A 1 H10H H -0.2232 0.1292 0.4609 0.121 Uiso 0.425(13) 1 calc PR A 1 C200 C -0.1788(5) -0.0933(9) 0.2920(10) 0.060(4) Uani 0.575(13) 1 d PGDU A 2 H20A H -0.1406 -0.1349 0.2898 0.072 Uiso 0.575(13) 1 calc PR A 2 C201 C -0.2313(6) -0.1102(10) 0.2149(9) 0.112(8) Uani 0.575(13) 1 d PGDU A 2 H20B H -0.2290 -0.1635 0.1600 0.134 Uiso 0.575(13) 1 calc PR A 2 C202 C -0.2871(5) -0.0493(11) 0.2182(8) 0.071(6) Uani 0.575(13) 1 d PGDU A 2 H20C H -0.3229 -0.0609 0.1655 0.085 Uiso 0.575(13) 1 calc PR A 2 C203 C -0.2903(3) 0.0285(10) 0.2985(8) 0.049(3) Uani 0.575(13) 1 d PGDU A 2 H20D H -0.3285 0.0702 0.3008 0.059 Uiso 0.575(13) 1 calc PR A 2 C204 C -0.2378(4) 0.0455(9) 0.3756(6) 0.064(4) Uani 0.575(13) 1 d PGDU A 2 H20E H -0.2401 0.0987 0.4305 0.077 Uiso 0.575(13) 1 calc PR A 2 C205 C -0.1820(3) -0.0154(9) 0.3723(7) 0.054(4) Uani 0.575(13) 1 d PGDU A 2 C206 C -0.1277(5) -0.0070(11) 0.4504(9) 0.051(3) Uani 0.575(13) 1 d PDU A 2 H20F H -0.1394 0.0288 0.5129 0.077 Uiso 0.575(13) 1 calc PR A 2 H20G H -0.0954 0.0403 0.4247 0.077 Uiso 0.575(13) 1 calc PR A 2 H20H H -0.1106 -0.0844 0.4677 0.077 Uiso 0.575(13) 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 0.0186(4) 0.0137(4) 0.0209(4) 0.000 0.0049(3) 0.000 N1 0.0231(18) 0.0194(17) 0.0213(18) -0.0004(14) 0.0045(14) 0.0002(15) C1 0.019(2) 0.024(2) 0.024(2) 0.0044(17) 0.0008(17) 0.0021(17) S1 0.0270(7) 0.0803(12) 0.0440(8) 0.0257(8) 0.0158(6) 0.0028(7) N3 0.0181(17) 0.0183(17) 0.0241(18) -0.0036(14) 0.0039(14) -0.0048(14) C3 0.023(2) 0.027(2) 0.034(3) 0.005(2) 0.0005(19) -0.0095(19) C4 0.024(2) 0.028(2) 0.030(2) 0.0057(19) 0.0009(18) -0.0075(19) C5 0.021(2) 0.019(2) 0.022(2) -0.0067(16) 0.0054(17) -0.0049(16) C6 0.024(2) 0.037(3) 0.025(2) 0.0002(19) 0.0038(18) -0.0157(19) C7 0.025(2) 0.030(2) 0.024(2) 0.0008(18) 0.0019(18) -0.0116(19) N5 0.044(3) 0.015(2) 0.022(3) 0.000 0.013(2) 0.000 C13 0.059(3) 0.018(2) 0.026(2) 0.0015(18) 0.015(2) 0.004(2) C14 0.054(3) 0.017(2) 0.024(2) -0.0019(17) 0.011(2) 0.001(2) C15 0.034(3) 0.016(3) 0.026(3) 0.000 0.012(3) 0.000 N6 0.015(2) 0.016(2) 0.021(2) 0.000 0.0001(19) 0.000 C18 0.025(2) 0.019(2) 0.029(2) -0.0022(17) 0.0083(18) -0.0019(17) C21 0.031(2) 0.018(2) 0.028(2) -0.0040(17) 0.0101(19) -0.0002(18) C22 0.026(3) 0.017(3) 0.025(3) 0.000 0.005(2) 0.000 C100 0.032(6) 0.026(6) 0.049(7) 0.012(6) -0.002(6) -0.011(5) C101 0.021(6) 0.013(5) 0.033(6) 0.010(4) 0.004(5) 0.004(4) C102 0.034(6) 0.035(6) 0.024(5) 0.018(4) 0.013(4) 0.010(5) C103 0.035(6) 0.071(9) 0.050(8) 0.027(7) 0.006(6) 0.001(6) C104 0.019(5) 0.032(6) 0.035(6) -0.005(5) 0.001(5) -0.019(5) C105 0.081(9) 0.041(7) 0.043(7) 0.001(6) -0.004(7) -0.055(7) C106 0.080(9) 0.063(9) 0.086(10) 0.010(7) -0.025(8) -0.015(7) C200 0.098(8) 0.039(6) 0.052(7) 0.001(5) 0.035(6) 0.022(6) C201 0.116(11) 0.101(11) 0.124(11) 0.003(9) 0.038(9) -0.007(9) C202 0.074(9) 0.055(8) 0.094(10) 0.016(7) 0.041(8) 0.007(6) C203 0.048(6) 0.066(7) 0.038(5) 0.040(5) 0.024(4) 0.034(5) C204 0.046(6) 0.094(8) 0.055(6) 0.048(6) 0.018(5) 0.026(6) C205 0.045(6) 0.070(8) 0.050(6) 0.038(6) 0.015(5) -0.009(6) C206 0.043(5) 0.057(6) 0.049(6) 0.015(5) -0.004(4) -0.016(5) _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 2.106(4) 2 ? Fe1 N1 2.106(4) . ? Fe1 N3 2.225(3) 2 ? Fe1 N3 2.225(3) . ? Fe1 N5 2.234(5) . ? Fe1 N6 2.249(5) 1_565 ? N1 C1 1.165(6) . ? C1 S1 1.622(5) . ? N3 C7 1.332(5) . ? N3 C3 1.339(6) . ? C3 C4 1.384(6) . ? C4 C5 1.397(6) . ? C5 C6 1.390(6) . ? C5 C5 1.483(8) 7_455 ? C6 C7 1.386(6) . ? N5 C13 1.330(6) 2 ? N5 C13 1.330(6) . ? C13 C14 1.387(6) . ? C14 C15 1.382(6) . ? C15 C14 1.382(6) 2 ? C15 C22 1.488(8) . ? N6 C18 1.342(5) . ? N6 C18 1.342(5) 2 ? N6 Fe1 2.249(5) 1_545 ? C18 C21 1.384(6) . ? C21 C22 1.385(5) . ? C22 C21 1.385(5) 2 ? C100 C101 1.3900 . ? C100 C105 1.3900 . ? C101 C102 1.3900 . ? C102 C103 1.3900 . ? C103 C104 1.3900 . ? C104 C105 1.3900 . ? C105 C106 1.383(15) . ? C200 C201 1.3900 . ? C200 C205 1.3900 . ? C201 C202 1.3900 . ? C202 C203 1.3900 . ? C203 C204 1.3900 . ? C204 C205 1.3900 . ? C205 C206 1.415(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 N1 Fe1 N1 177.2(2) 2 . ? N1 Fe1 N3 89.68(13) 2 2 ? N1 Fe1 N3 90.26(13) . 2 ? N1 Fe1 N3 90.26(13) 2 . ? N1 Fe1 N3 89.68(13) . . ? N3 Fe1 N3 177.40(19) 2 . ? N1 Fe1 N5 88.61(10) 2 . ? N1 Fe1 N5 88.61(10) . . ? N3 Fe1 N5 88.70(9) 2 . ? N3 Fe1 N5 88.70(9) . . ? N1 Fe1 N6 91.39(10) 2 1_565 ? N1 Fe1 N6 91.39(10) . 1_565 ? N3 Fe1 N6 91.30(9) 2 1_565 ? N3 Fe1 N6 91.30(9) . 1_565 ? N5 Fe1 N6 180.0 . 1_565 ? C1 N1 Fe1 157.6(4) . . ? N1 C1 S1 179.0(4) . . ? C7 N3 C3 116.6(4) . . ? C7 N3 Fe1 121.0(3) . . ? C3 N3 Fe1 122.3(3) . . ? N3 C3 C4 123.7(4) . . ? C3 C4 C5 119.9(4) . . ? C6 C5 C4 116.0(4) . . ? C6 C5 C5 121.9(5) . 7_455 ? C4 C5 C5 122.1(5) . 7_455 ? C7 C6 C5 120.3(4) . . ? N3 C7 C6 123.5(4) . . ? C13 N5 C13 117.3(6) 2 . ? C13 N5 Fe1 121.4(3) 2 . ? C13 N5 Fe1 121.4(3) . . ? N5 C13 C14 123.2(5) . . ? C15 C14 C13 119.5(5) . . ? C14 C15 C14 117.4(6) 2 . ? C14 C15 C22 121.3(3) 2 . ? C14 C15 C22 121.3(3) . . ? C18 N6 C18 116.3(5) . 2 ? C18 N6 Fe1 121.9(3) . 1_545 ? C18 N6 Fe1 121.9(3) 2 1_545 ? N6 C18 C21 123.6(4) . . ? C18 C21 C22 119.5(4) . . ? C21 C22 C21 117.5(6) . 2 ? C21 C22 C15 121.3(3) . . ? C21 C22 C15 121.3(3) 2 . ? C101 C100 C105 120.0 . . ? C100 C101 C102 120.0 . . ? C103 C102 C101 120.0 . . ? C102 C103 C104 120.0 . . ? C103 C104 C105 120.0 . . ? C106 C105 C104 108.4(11) . . ? C106 C105 C100 131.5(11) . . ? C104 C105 C100 120.0 . . ? C201 C200 C205 120.0 . . ? C200 C201 C202 120.0 . . ? C201 C202 C203 120.0 . . ? C204 C203 C202 120.0 . . ? C205 C204 C203 120.0 . . ? C204 C205 C200 120.0 . . ? C204 C205 C206 123.4(8) . . ? C200 C205 C206 116.6(9) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.075 _refine_diff_density_min -2.032 _refine_diff_density_rms 0.122 #===END data_1-2nitrobenzene _database_code_depnum_ccdc_archive 'CCDC 771543' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H26 Fe1 N8 O4 S2' _chemical_formula_weight 730.6 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.471(6) _cell_length_b 11.605(3) _cell_length_c 13.205(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.083(15) _cell_angle_gamma 90.00 _cell_volume 3354.1(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4787 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.60 _exptl_crystal_description Lath _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.626 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8345 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11770 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.86 _reflns_number_total 3856 _reflns_number_gt 3218 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0243P)^2^+4.9893P] 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 3856 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0776 _refine_ls_wR_factor_gt 0.0720 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.0000 0.27741(3) 0.2500 0.01175(9) Uani 1 2 d S . . N1 N 0.03573(7) 0.27474(12) 0.11514(11) 0.0169(3) Uani 1 1 d . . . C1 C 0.07318(8) 0.29540(14) 0.06861(13) 0.0163(3) Uani 1 1 d . . . S1 S 0.12495(2) 0.32831(4) 0.00354(4) 0.02519(12) Uani 1 1 d . . . N3 N -0.09677(6) 0.27235(12) 0.15495(10) 0.0144(3) Uani 1 1 d . . . C3 C -0.11748(8) 0.34202(15) 0.07359(13) 0.0186(4) Uani 1 1 d . . . H3A H -0.0904 0.3984 0.0573 0.022 Uiso 1 1 calc R . . C4 C -0.17648(8) 0.33636(15) 0.01155(13) 0.0191(4) Uani 1 1 d . . . H4A H -0.1885 0.3881 -0.0451 0.023 Uiso 1 1 calc R . . C5 C -0.21804(7) 0.25485(14) 0.03235(12) 0.0141(3) Uani 1 1 d . . . C6 C -0.19649(8) 0.18325(15) 0.11804(14) 0.0193(4) Uani 1 1 d . . . H6A H -0.2225 0.1263 0.1364 0.023 Uiso 1 1 calc R . . C7 C -0.13706(8) 0.19527(15) 0.17623(13) 0.0185(4) Uani 1 1 d . . . H7A H -0.1240 0.1461 0.2346 0.022 Uiso 1 1 calc R . . N5 N 0.0000 0.08615(16) 0.2500 0.0145(4) Uani 1 2 d S . . C13 C -0.01344(8) 0.02575(14) 0.16062(13) 0.0171(3) Uani 1 1 d . . . H13A H -0.0231 0.0670 0.0969 0.021 Uiso 1 1 calc R . . C14 C -0.01390(8) -0.09347(14) 0.15699(13) 0.0182(4) Uani 1 1 d . . . H14A H -0.0235 -0.1324 0.0921 0.022 Uiso 1 1 calc R . . C15 C 0.0000 -0.1560(2) 0.2500 0.0157(5) Uani 1 2 d S . . N6 N 0.0000 -0.52708(16) 0.2500 0.0148(4) Uani 1 2 d S . . C18 C -0.01958(8) -0.46595(14) 0.32312(13) 0.0173(3) Uani 1 1 d . . . H18A H -0.0337 -0.5070 0.3753 0.021 Uiso 1 1 calc R . . C21 C -0.02016(8) -0.34631(14) 0.32637(13) 0.0176(3) Uani 1 1 d . . . H21A H -0.0341 -0.3074 0.3799 0.021 Uiso 1 1 calc R . . C22 C 0.0000 -0.2839(2) 0.2500 0.0153(5) Uani 1 2 d S . . C101 C 0.19451(9) 0.51575(17) -0.25256(14) 0.0255(4) Uani 1 1 d . . . H10D H 0.1598 0.5407 -0.3031 0.031 Uiso 1 1 calc R . . C102 C 0.19078(10) 0.41790(18) -0.19434(16) 0.0296(4) Uani 1 1 d . . . H10E H 0.1535 0.3761 -0.2047 0.035 Uiso 1 1 calc R . . C103 C 0.24171(10) 0.38078(19) -0.12054(17) 0.0331(5) Uani 1 1 d . . . H10C H 0.2393 0.3124 -0.0822 0.040 Uiso 1 1 calc R . . C104 C 0.29607(9) 0.44273(18) -0.10234(15) 0.0295(4) Uani 1 1 d . . . H10B H 0.3306 0.4188 -0.0509 0.035 Uiso 1 1 calc R . . C105 C 0.29827(9) 0.54021(16) -0.16138(15) 0.0239(4) Uani 1 1 d . . . C106 C 0.24875(9) 0.57764(16) -0.23752(15) 0.0255(4) Uani 1 1 d . . . H10A H 0.2519 0.6439 -0.2783 0.031 Uiso 1 1 calc R . . N100 N 0.35558(8) 0.60810(17) -0.14213(15) 0.0357(4) Uani 1 1 d . . . O100 O 0.36010(9) 0.68410(16) -0.20343(19) 0.0662(6) Uani 1 1 d . . . O101 O 0.39546(7) 0.58629(19) -0.06525(13) 0.0545(5) 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 Fe1 0.01096(17) 0.00798(16) 0.01512(16) 0.000 0.00044(12) 0.000 N1 0.0184(8) 0.0127(7) 0.0189(7) -0.0006(6) 0.0030(6) 0.0000(6) C1 0.0186(9) 0.0108(8) 0.0168(8) -0.0016(6) -0.0018(7) 0.0014(6) S1 0.0214(3) 0.0306(3) 0.0253(2) 0.00057(19) 0.00894(18) -0.0026(2) N3 0.0126(7) 0.0117(7) 0.0179(7) -0.0006(5) 0.0009(5) 0.0007(5) C3 0.0149(9) 0.0176(9) 0.0218(8) 0.0034(7) 0.0008(7) -0.0043(7) C4 0.0173(9) 0.0191(9) 0.0188(8) 0.0069(7) 0.0002(7) -0.0023(7) C5 0.0124(8) 0.0130(8) 0.0158(8) -0.0020(6) 0.0012(6) 0.0010(6) C6 0.0140(9) 0.0179(8) 0.0243(9) 0.0065(7) 0.0011(7) -0.0036(7) C7 0.0151(9) 0.0169(8) 0.0213(8) 0.0066(7) -0.0005(7) -0.0009(7) N5 0.0124(10) 0.0112(9) 0.0184(10) 0.000 0.0003(8) 0.000 C13 0.0192(9) 0.0131(8) 0.0175(8) 0.0018(6) 0.0006(6) -0.0005(7) C14 0.0216(9) 0.0124(8) 0.0190(8) -0.0023(6) 0.0011(7) -0.0015(7) C15 0.0140(12) 0.0103(11) 0.0213(12) 0.000 0.0012(9) 0.000 N6 0.0107(10) 0.0095(9) 0.0218(10) 0.000 -0.0014(7) 0.000 C18 0.0159(9) 0.0125(8) 0.0223(8) 0.0014(7) 0.0018(6) -0.0011(7) C21 0.0173(9) 0.0131(8) 0.0212(8) -0.0008(6) 0.0019(7) 0.0015(7) C22 0.0122(11) 0.0099(11) 0.0213(11) 0.000 -0.0015(9) 0.000 C101 0.0221(10) 0.0316(11) 0.0215(9) -0.0054(8) 0.0019(7) 0.0037(8) C102 0.0260(11) 0.0313(11) 0.0332(11) -0.0039(9) 0.0104(8) -0.0028(9) C103 0.0350(12) 0.0315(11) 0.0366(11) 0.0101(9) 0.0162(9) 0.0046(9) C104 0.0262(11) 0.0374(12) 0.0243(9) 0.0041(8) 0.0045(8) 0.0097(9) C105 0.0227(10) 0.0230(9) 0.0269(9) -0.0085(8) 0.0074(7) 0.0001(8) C106 0.0325(11) 0.0199(9) 0.0253(9) 0.0006(7) 0.0091(8) 0.0043(8) N100 0.0249(10) 0.0355(11) 0.0475(11) -0.0149(9) 0.0097(8) -0.0007(8) O100 0.0404(11) 0.0409(11) 0.1139(18) 0.0242(11) 0.0104(11) -0.0116(8) O101 0.0252(9) 0.0934(15) 0.0417(10) -0.0178(10) 0.0007(7) -0.0082(9) _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 2.1128(15) . ? Fe1 N1 2.1129(15) 2 ? Fe1 N5 2.220(2) . ? Fe1 N3 2.2520(15) 2 ? Fe1 N3 2.2520(15) . ? Fe1 N6 2.269(2) 1_565 ? N1 C1 1.174(2) . ? C1 S1 1.6399(19) . ? N3 C3 1.341(2) . ? N3 C7 1.347(2) . ? C3 C4 1.393(2) . ? C4 C5 1.399(2) . ? C5 C6 1.399(2) . ? C5 C5 1.500(3) 7_455 ? C6 C7 1.389(2) . ? N5 C13 1.3469(19) . ? N5 C13 1.3469(19) 2 ? C13 C14 1.384(2) . ? C14 C15 1.399(2) . ? C15 C14 1.399(2) 2 ? C15 C22 1.485(3) . ? N6 C18 1.350(2) . ? N6 C18 1.350(2) 2 ? N6 Fe1 2.269(2) 1_545 ? C18 C21 1.389(2) . ? C21 C22 1.398(2) . ? C22 C21 1.398(2) 2 ? C101 C102 1.384(3) . ? C101 C106 1.390(3) . ? C102 C103 1.393(3) . ? C103 C104 1.391(3) . ? C104 C105 1.381(3) . ? C105 C106 1.390(3) . ? C105 N100 1.482(3) . ? N100 O100 1.217(3) . ? N100 O101 1.219(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 178.32(8) . 2 ? N1 Fe1 N5 89.16(4) . . ? N1 Fe1 N5 89.16(4) 2 . ? N1 Fe1 N3 88.06(6) . 2 ? N1 Fe1 N3 91.90(6) 2 2 ? N5 Fe1 N3 88.50(4) . 2 ? N1 Fe1 N3 91.90(6) . . ? N1 Fe1 N3 88.05(6) 2 . ? N5 Fe1 N3 88.50(4) . . ? N3 Fe1 N3 177.01(7) 2 . ? N1 Fe1 N6 90.84(4) . 1_565 ? N1 Fe1 N6 90.84(4) 2 1_565 ? N5 Fe1 N6 180.0 . 1_565 ? N3 Fe1 N6 91.50(4) 2 1_565 ? N3 Fe1 N6 91.49(4) . 1_565 ? C1 N1 Fe1 153.21(13) . . ? N1 C1 S1 178.30(15) . . ? C3 N3 C7 116.10(14) . . ? C3 N3 Fe1 123.15(11) . . ? C7 N3 Fe1 120.72(11) . . ? N3 C3 C4 123.64(16) . . ? C3 C4 C5 120.33(16) . . ? C6 C5 C4 115.84(15) . . ? C6 C5 C5 121.84(19) . 7_455 ? C4 C5 C5 122.31(18) . 7_455 ? C7 C6 C5 120.09(16) . . ? N3 C7 C6 123.97(16) . . ? C13 N5 C13 117.3(2) . 2 ? C13 N5 Fe1 121.36(10) . . ? C13 N5 Fe1 121.36(10) 2 . ? N5 C13 C14 123.29(16) . . ? C13 C14 C15 119.29(16) . . ? C14 C15 C14 117.6(2) . 2 ? C14 C15 C22 121.22(11) . . ? C14 C15 C22 121.22(11) 2 . ? C18 N6 C18 116.6(2) . 2 ? C18 N6 Fe1 121.71(10) . 1_545 ? C18 N6 Fe1 121.71(10) 2 1_545 ? N6 C18 C21 123.67(16) . . ? C18 C21 C22 119.25(16) . . ? C21 C22 C21 117.6(2) . 2 ? C21 C22 C15 121.21(11) . . ? C21 C22 C15 121.21(11) 2 . ? C102 C101 C106 120.39(18) . . ? C101 C102 C103 119.92(19) . . ? C104 C103 C102 120.76(19) . . ? C105 C104 C103 117.91(19) . . ? C104 C105 C106 122.64(18) . . ? C104 C105 N100 118.65(18) . . ? C106 C105 N100 118.71(18) . . ? C101 C106 C105 118.33(18) . . ? O100 N100 O101 123.2(2) . . ? O100 N100 C105 118.13(19) . . ? O101 N100 C105 118.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Fe1 N1 C1 -118.9(3) 2 . . . ? N5 Fe1 N1 C1 -118.8(3) . . . . ? N3 Fe1 N1 C1 -30.3(3) 2 . . . ? N3 Fe1 N1 C1 152.7(3) . . . . ? N6 Fe1 N1 C1 61.2(3) 1_565 . . . ? Fe1 N1 C1 S1 -72(5) . . . . ? N1 Fe1 N3 C3 -48.41(14) . . . . ? N1 Fe1 N3 C3 133.27(14) 2 . . . ? N5 Fe1 N3 C3 -137.52(13) . . . . ? N3 Fe1 N3 C3 -137.54(13) 2 . . . ? N6 Fe1 N3 C3 42.48(13) 1_565 . . . ? N1 Fe1 N3 C7 129.87(13) . . . . ? N1 Fe1 N3 C7 -48.45(13) 2 . . . ? N5 Fe1 N3 C7 40.76(13) . . . . ? N3 Fe1 N3 C7 40.74(13) 2 . . . ? N6 Fe1 N3 C7 -139.24(13) 1_565 . . . ? C7 N3 C3 C4 -1.2(3) . . . . ? Fe1 N3 C3 C4 177.17(13) . . . . ? N3 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C3 C4 C5 C5 -179.81(19) . . . 7_455 ? C4 C5 C6 C7 -0.3(3) . . . . ? C5 C5 C6 C7 -179.75(19) 7_455 . . . ? C3 N3 C7 C6 1.7(3) . . . . ? Fe1 N3 C7 C6 -176.72(14) . . . . ? C5 C6 C7 N3 -1.0(3) . . . . ? N1 Fe1 N5 C13 -36.55(10) . . . . ? N1 Fe1 N5 C13 143.45(10) 2 . . . ? N3 Fe1 N5 C13 -124.63(9) 2 . . . ? N3 Fe1 N5 C13 55.37(9) . . . . ? N6 Fe1 N5 C13 88(4) 1_565 . . . ? N1 Fe1 N5 C13 143.45(10) . . . 2 ? N1 Fe1 N5 C13 -36.55(10) 2 . . 2 ? N3 Fe1 N5 C13 55.37(9) 2 . . 2 ? N3 Fe1 N5 C13 -124.63(9) . . . 2 ? N6 Fe1 N5 C13 -92(4) 1_565 . . 2 ? C13 N5 C13 C14 -0.10(13) 2 . . . ? Fe1 N5 C13 C14 179.90(13) . . . . ? N5 C13 C14 C15 0.2(3) . . . . ? C13 C14 C15 C14 -0.10(12) . . . 2 ? C13 C14 C15 C22 179.91(12) . . . . ? C18 N6 C18 C21 -0.26(12) 2 . . . ? Fe1 N6 C18 C21 179.74(12) 1_545 . . . ? N6 C18 C21 C22 0.5(2) . . . . ? C18 C21 C22 C21 -0.24(11) . . . 2 ? C18 C21 C22 C15 179.76(11) . . . . ? C14 C15 C22 C21 -143.61(12) . . . . ? C14 C15 C22 C21 36.39(12) 2 . . . ? C14 C15 C22 C21 36.39(12) . . . 2 ? C14 C15 C22 C21 -143.61(12) 2 . . 2 ? C106 C101 C102 C103 -0.3(3) . . . . ? C101 C102 C103 C104 1.8(3) . . . . ? C102 C103 C104 C105 -1.5(3) . . . . ? C103 C104 C105 C106 -0.3(3) . . . . ? C103 C104 C105 N100 179.24(18) . . . . ? C102 C101 C106 C105 -1.4(3) . . . . ? C104 C105 C106 C101 1.7(3) . . . . ? N100 C105 C106 C101 -177.77(16) . . . . ? C104 C105 N100 O100 170.0(2) . . . . ? C106 C105 N100 O100 -10.5(3) . . . . ? C104 C105 N100 O101 -10.9(3) . . . . ? C106 C105 N100 O101 168.58(19) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.398 _refine_diff_density_min -0.517 _refine_diff_density_rms 0.064 #===END data_1-2Ether _database_code_depnum_ccdc_archive 'CCDC 771544' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H36 Fe N6 O2 S2' _chemical_formula_weight 632.62 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 Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.5165(11) _cell_length_b 11.4813(11) _cell_length_c 13.1038(11) _cell_angle_alpha 90.00 _cell_angle_beta 106.602(5) _cell_angle_gamma 90.00 _cell_volume 1660.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2540 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 26.79 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.615 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.665 _exptl_absorpt_correction_T_max 0.745 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_% 0 _diffrn_reflns_number 14004 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3826 _reflns_number_gt 2944 _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^)+(0.0394P)^2^+1.1048P] 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 3826 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.5000 0.28812(4) 0.7500 0.01239(12) Uani 1 2 d S . . N1 N 0.44797(16) 0.28443(16) 0.58174(13) 0.0171(4) Uani 1 1 d . . . C1 C 0.37466(19) 0.30923(18) 0.50260(16) 0.0168(4) Uani 1 1 d . . . S1 S 0.27032(6) 0.34393(6) 0.39459(5) 0.03297(18) Uani 1 1 d . . . N3 N 0.30720(15) 0.29081(15) 0.74877(13) 0.0152(4) Uani 1 1 d . . . C3 C 0.2182(2) 0.2457(2) 0.66884(17) 0.0206(5) Uani 1 1 d . . . H3A H 0.2396 0.2096 0.6115 0.025 Uiso 1 1 calc R . . C4 C 0.0972(2) 0.2490(2) 0.66550(17) 0.0214(5) Uani 1 1 d . . . H4A H 0.0373 0.2174 0.6064 0.026 Uiso 1 1 calc R . . C5 C 0.06426(18) 0.29908(19) 0.74938(16) 0.0178(4) Uani 1 1 d . . . C6 C 0.1554(2) 0.3459(2) 0.83224(18) 0.0229(5) Uani 1 1 d . . . H6A H 0.1363 0.3807 0.8912 0.028 Uiso 1 1 calc R . . C7 C 0.27441(19) 0.3416(2) 0.82866(17) 0.0201(5) Uani 1 1 d . . . H7A H 0.3355 0.3762 0.8852 0.024 Uiso 1 1 calc R . . N5 N 0.5000 0.0957(2) 0.7500 0.0160(5) Uani 1 2 d S . . C13 C 0.4790(2) 0.03506(19) 0.83038(17) 0.0208(5) Uani 1 1 d . . . H13A H 0.4632 0.0768 0.8876 0.025 Uiso 1 1 calc R . . C14 C 0.4791(2) -0.08529(19) 0.83386(17) 0.0214(5) Uani 1 1 d . . . H14A H 0.4651 -0.1248 0.8929 0.026 Uiso 1 1 calc R . . C15 C 0.5000 -0.1478(3) 0.7500 0.0169(6) Uani 1 2 d S . . N6 N 0.5000 -0.5199(2) 0.7500 0.0162(5) Uani 1 2 d S . . C18 C 0.42575(19) -0.45885(19) 0.67039(17) 0.0184(4) Uani 1 1 d . . . H18A H 0.3719 -0.5005 0.6136 0.022 Uiso 1 1 calc R . . C19 C 0.42364(19) -0.33845(19) 0.66672(17) 0.0187(5) Uani 1 1 d . . . H19A H 0.3707 -0.2989 0.6080 0.022 Uiso 1 1 calc R . . C20 C 0.5000 -0.2764(3) 0.7500 0.0170(6) Uani 1 2 d S . . O100 O 0.14127(18) 0.1860(2) 0.04695(15) 0.0452(5) Uani 1 1 d . . . C101 C 0.0769(3) 0.3582(4) 0.1200(3) 0.0615(10) Uani 1 1 d . . . H10A H 0.0520 0.3878 0.1807 0.092 Uiso 1 1 calc R . . H10B H 0.0121 0.3720 0.0541 0.092 Uiso 1 1 calc R . . H10C H 0.1506 0.3986 0.1164 0.092 Uiso 1 1 calc R . . C102 C 0.1020(3) 0.2276(4) 0.1338(2) 0.0630(11) Uani 1 1 d . . . H10D H 0.1653 0.2129 0.2017 0.076 Uiso 1 1 calc R . . H10E H 0.0274 0.1861 0.1361 0.076 Uiso 1 1 calc R . . C103 C 0.1709(3) 0.0663(3) 0.0544(3) 0.0518(8) Uani 1 1 d . . . H10F H 0.0998 0.0199 0.0581 0.062 Uiso 1 1 calc R . . H10G H 0.2377 0.0514 0.1198 0.062 Uiso 1 1 calc R . . C104 C 0.2088(3) 0.0313(3) -0.0418(3) 0.0608(9) Uani 1 1 d . . . H10H H 0.2369 -0.0497 -0.0341 0.091 Uiso 1 1 calc R . . H10I H 0.2747 0.0821 -0.0485 0.091 Uiso 1 1 calc R . . H10J H 0.1397 0.0386 -0.1057 0.091 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 0.0100(2) 0.0098(2) 0.0175(2) 0.000 0.00406(15) 0.000 N1 0.0161(9) 0.0148(9) 0.0208(9) -0.0007(7) 0.0058(7) 0.0000(8) C1 0.0167(10) 0.0139(11) 0.0227(10) -0.0022(8) 0.0101(8) -0.0012(8) S1 0.0262(3) 0.0444(4) 0.0234(3) 0.0049(3) -0.0008(2) 0.0080(3) N3 0.0123(8) 0.0120(9) 0.0215(8) -0.0005(7) 0.0049(7) -0.0009(7) C3 0.0157(11) 0.0256(13) 0.0216(10) -0.0059(9) 0.0071(8) -0.0035(9) C4 0.0139(11) 0.0289(13) 0.0205(10) -0.0041(9) 0.0032(8) -0.0055(9) C5 0.0137(11) 0.0176(11) 0.0222(10) 0.0022(9) 0.0050(8) 0.0014(9) C6 0.0167(11) 0.0272(13) 0.0270(11) -0.0080(10) 0.0096(9) 0.0001(10) C7 0.0122(10) 0.0231(12) 0.0242(11) -0.0083(9) 0.0040(8) -0.0025(9) N5 0.0135(12) 0.0134(13) 0.0226(12) 0.000 0.0077(10) 0.000 C13 0.0288(12) 0.0142(11) 0.0227(10) -0.0017(9) 0.0129(9) -0.0023(10) C14 0.0302(13) 0.0154(12) 0.0215(10) 0.0018(9) 0.0117(9) -0.0028(10) C15 0.0160(15) 0.0106(15) 0.0233(15) 0.000 0.0044(12) 0.000 N6 0.0126(12) 0.0117(13) 0.0236(12) 0.000 0.0042(10) 0.000 C18 0.0152(10) 0.0142(11) 0.0238(10) -0.0020(8) 0.0022(8) 0.0001(9) C19 0.0174(11) 0.0143(11) 0.0232(11) 0.0011(9) 0.0037(8) 0.0022(9) C20 0.0175(15) 0.0115(15) 0.0236(15) 0.000 0.0085(12) 0.000 O100 0.0334(11) 0.0653(15) 0.0349(10) 0.0032(10) 0.0064(8) 0.0051(10) C101 0.0391(18) 0.099(3) 0.0462(18) -0.0207(19) 0.0111(14) 0.0030(19) C102 0.058(2) 0.098(3) 0.0333(16) -0.0118(18) 0.0133(15) -0.023(2) C103 0.0362(17) 0.057(2) 0.0566(19) 0.0170(16) 0.0039(14) -0.0053(16) C104 0.064(2) 0.051(2) 0.068(2) 0.0109(18) 0.0215(18) 0.0176(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 Fe1 N1 2.1136(17) 2_656 ? Fe1 N1 2.1136(17) . ? Fe1 N6 2.204(3) 1_565 ? Fe1 N5 2.209(3) . ? Fe1 N3 2.2160(17) 2_656 ? Fe1 N3 2.2161(17) . ? N1 C1 1.170(3) . ? C1 S1 1.623(2) . ? N3 C3 1.342(3) . ? N3 C7 1.344(3) . ? C3 C4 1.383(3) . ? C3 H3A 0.9500 . ? C4 C5 1.386(3) . ? C4 H4A 0.9500 . ? C5 C6 1.385(3) . ? C5 C5 1.485(4) 2_556 ? C6 C7 1.386(3) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? N5 C13 1.341(2) . ? N5 C13 1.341(2) 2_656 ? C13 C14 1.383(3) . ? C13 H13A 0.9500 . ? C14 C15 1.390(3) . ? C14 H14A 0.9500 . ? C15 C14 1.390(3) 2_656 ? C15 C20 1.476(4) . ? N6 C18 1.342(2) . ? N6 C18 1.342(2) 2_656 ? N6 Fe1 2.204(2) 1_545 ? C18 C19 1.383(3) . ? C18 H18A 0.9500 . ? C19 C20 1.387(3) . ? C19 H19A 0.9500 . ? C20 C19 1.387(3) 2_656 ? O100 C103 1.413(4) . ? O100 C102 1.423(4) . ? C101 C102 1.528(5) . ? C101 H10A 0.9800 . ? C101 H10B 0.9800 . ? C101 H10C 0.9800 . ? C102 H10D 0.9900 . ? C102 H10E 0.9900 . ? C103 C104 1.502(5) . ? C103 H10F 0.9900 . ? C103 H10G 0.9900 . ? C104 H10H 0.9800 . ? C104 H10I 0.9800 . ? C104 H10J 0.9800 . ? 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 N1 177.71(10) 2_656 . ? N1 Fe1 N6 91.15(5) 2_656 1_565 ? N1 Fe1 N6 91.15(5) . 1_565 ? N1 Fe1 N5 88.85(5) 2_656 . ? N1 Fe1 N5 88.85(5) . . ? N6 Fe1 N5 180.0 1_565 . ? N1 Fe1 N3 90.45(6) 2_656 2_656 ? N1 Fe1 N3 89.58(6) . 2_656 ? N6 Fe1 N3 89.20(5) 1_565 2_656 ? N5 Fe1 N3 90.80(5) . 2_656 ? N1 Fe1 N3 89.58(6) 2_656 . ? N1 Fe1 N3 90.45(6) . . ? N6 Fe1 N3 89.20(5) 1_565 . ? N5 Fe1 N3 90.80(5) . . ? N3 Fe1 N3 178.40(9) 2_656 . ? C1 N1 Fe1 146.87(16) . . ? N1 C1 S1 178.5(2) . . ? C3 N3 C7 116.99(18) . . ? C3 N3 Fe1 122.69(14) . . ? C7 N3 Fe1 120.30(13) . . ? N3 C3 C4 123.5(2) . . ? N3 C3 H3A 118.3 . . ? C4 C3 H3A 118.3 . . ? C3 C4 C5 119.2(2) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C6 C5 C4 117.72(19) . . ? C6 C5 C5 121.7(2) . 2_556 ? C4 C5 C5 120.5(2) . 2_556 ? C5 C6 C7 119.7(2) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? N3 C7 C6 122.86(19) . . ? N3 C7 H7A 118.6 . . ? C6 C7 H7A 118.6 . . ? C13 N5 C13 117.4(3) . 2_656 ? C13 N5 Fe1 121.29(13) . . ? C13 N5 Fe1 121.29(13) 2_656 . ? N5 C13 C14 123.1(2) . . ? N5 C13 H13A 118.4 . . ? C14 C13 H13A 118.4 . . ? C13 C14 C15 119.3(2) . . ? C13 C14 H14A 120.4 . . ? C15 C14 H14A 120.4 . . ? C14 C15 C14 117.8(3) 2_656 . ? C14 C15 C20 121.09(14) 2_656 . ? C14 C15 C20 121.10(14) . . ? C18 N6 C18 117.0(3) . 2_656 ? C18 N6 Fe1 121.48(13) . 1_545 ? C18 N6 Fe1 121.49(13) 2_656 1_545 ? N6 C18 C19 123.4(2) . . ? N6 C18 H18A 118.3 . . ? C19 C18 H18A 118.3 . . ? C18 C19 C20 119.0(2) . . ? C18 C19 H19A 120.5 . . ? C20 C19 H19A 120.5 . . ? C19 C20 C19 118.2(3) . 2_656 ? C19 C20 C15 120.92(14) . . ? C19 C20 C15 120.92(14) 2_656 . ? C103 O100 C102 113.4(3) . . ? C102 C101 H10A 109.5 . . ? C102 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? C102 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? O100 C102 C101 109.1(3) . . ? O100 C102 H10D 109.9 . . ? C101 C102 H10D 109.9 . . ? O100 C102 H10E 109.9 . . ? C101 C102 H10E 109.9 . . ? H10D C102 H10E 108.3 . . ? O100 C103 C104 109.0(3) . . ? O100 C103 H10F 109.9 . . ? C104 C103 H10F 109.9 . . ? O100 C103 H10G 109.9 . . ? C104 C103 H10G 109.9 . . ? H10F C103 H10G 108.3 . . ? C103 C104 H10H 109.5 . . ? C103 C104 H10I 109.5 . . ? H10H C104 H10I 109.5 . . ? C103 C104 H10J 109.5 . . ? H10H C104 H10J 109.5 . . ? H10I C104 H10J 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Fe1 N1 C1 118.4(3) 2_656 . . . ? N6 Fe1 N1 C1 -61.6(3) 1_565 . . . ? N5 Fe1 N1 C1 118.4(3) . . . . ? N3 Fe1 N1 C1 -150.8(3) 2_656 . . . ? N3 Fe1 N1 C1 27.6(3) . . . . ? Fe1 N1 C1 S1 -20(8) . . . . ? N1 Fe1 N3 C3 -150.98(17) 2_656 . . . ? N1 Fe1 N3 C3 26.73(17) . . . . ? N6 Fe1 N3 C3 117.87(17) 1_565 . . . ? N5 Fe1 N3 C3 -62.13(17) . . . . ? N3 Fe1 N3 C3 117.90(17) 2_656 . . . ? N1 Fe1 N3 C7 30.82(17) 2_656 . . . ? N1 Fe1 N3 C7 -151.47(17) . . . . ? N6 Fe1 N3 C7 -60.33(16) 1_565 . . . ? N5 Fe1 N3 C7 119.67(16) . . . . ? N3 Fe1 N3 C7 -60.30(16) 2_656 . . . ? C7 N3 C3 C4 -0.2(3) . . . . ? Fe1 N3 C3 C4 -178.41(17) . . . . ? N3 C3 C4 C5 -1.4(4) . . . . ? C3 C4 C5 C6 1.3(3) . . . . ? C3 C4 C5 C5 -177.11(18) . . . 2_556 ? C4 C5 C6 C7 0.2(3) . . . . ? C5 C5 C6 C7 178.60(18) 2_556 . . . ? C3 N3 C7 C6 1.8(3) . . . . ? Fe1 N3 C7 C6 -179.93(18) . . . . ? C5 C6 C7 N3 -1.8(4) . . . . ? N1 Fe1 N5 C13 27.45(13) 2_656 . . . ? N1 Fe1 N5 C13 -152.55(13) . . . . ? N6 Fe1 N5 C13 -120(14) 1_565 . . . ? N3 Fe1 N5 C13 117.88(12) 2_656 . . . ? N3 Fe1 N5 C13 -62.11(12) . . . . ? N1 Fe1 N5 C13 -152.55(13) 2_656 . . 2_656 ? N1 Fe1 N5 C13 27.45(13) . . . 2_656 ? N6 Fe1 N5 C13 60(14) 1_565 . . 2_656 ? N3 Fe1 N5 C13 -62.12(12) 2_656 . . 2_656 ? N3 Fe1 N5 C13 117.88(12) . . . 2_656 ? C13 N5 C13 C14 0.52(17) 2_656 . . . ? Fe1 N5 C13 C14 -179.48(17) . . . . ? N5 C13 C14 C15 -1.0(3) . . . . ? C13 C14 C15 C14 0.48(16) . . . 2_656 ? C13 C14 C15 C20 -179.52(16) . . . . ? C18 N6 C18 C19 0.66(16) 2_656 . . . ? Fe1 N6 C18 C19 -179.34(16) 1_545 . . . ? N6 C18 C19 C20 -1.3(3) . . . . ? C18 C19 C20 C19 0.60(14) . . . 2_656 ? C18 C19 C20 C15 -179.40(14) . . . . ? C14 C15 C20 C19 -56.26(16) 2_656 . . . ? C14 C15 C20 C19 123.73(15) . . . . ? C14 C15 C20 C19 123.73(16) 2_656 . . 2_656 ? C14 C15 C20 C19 -56.27(15) . . . 2_656 ? C103 O100 C102 C101 177.9(3) . . . . ? C102 O100 C103 C104 179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.415 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.067 #===END data_1-4acetone _database_code_depnum_ccdc_archive 'CCDC 771545' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H40 Fe N6 O4 S2' _chemical_formula_weight 716.71 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' 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 Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.5535(19) _cell_length_b 11.5357(18) _cell_length_c 15.450(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.365(12) _cell_angle_gamma 90.00 _cell_volume 1875.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1970 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 23.12 _exptl_crystal_description Prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.556 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.574 _exptl_absorpt_correction_T_max 0.745 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 4195 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1181 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.44 _reflns_number_total 4195 _reflns_number_gt 2515 _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^)+(0.2000P)^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 4195 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2478 _refine_ls_R_factor_gt 0.1937 _refine_ls_wR_factor_ref 0.5303 _refine_ls_wR_factor_gt 0.5167 _refine_ls_goodness_of_fit_ref 1.880 _refine_ls_restrained_S_all 1.880 _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 0.0000 -0.33358(19) -0.2500 0.0292(8) Uani 1 2 d S . . S1 S 0.2493(5) -0.3235(6) 0.0925(4) 0.0913(19) Uani 1 1 d . . . N1 N 0.0847(9) -0.3327(9) -0.0985(9) 0.037(3) Uani 1 1 d . . . N3 N -0.1920(8) -0.3312(8) -0.2468(7) 0.032(2) Uani 1 1 d . . . N5 N 0.0000 -0.5256(13) -0.2500 0.037(3) Uani 1 2 d S . . N6 N 0.0000 -0.1418(10) -0.2500 0.033(3) Uani 1 2 d S . . C1 C 0.1508(13) -0.3312(13) -0.0200(11) 0.047(3) Uani 1 1 d . . . C3 C -0.2111(11) -0.3647(12) -0.1731(9) 0.038(3) Uani 1 1 d . . . H3A H -0.1387 -0.3903 -0.1194 0.046 Uiso 1 1 calc R . . C4 C -0.3284(11) -0.3668(13) -0.1654(10) 0.045(3) Uani 1 1 d . . . H4A H -0.3358 -0.3889 -0.1087 0.054 Uiso 1 1 calc R . . C5 C -0.4371(10) -0.3325(10) -0.2508(8) 0.033(3) Uani 1 1 d . . . C6 C -0.4136(12) -0.2941(12) -0.3282(10) 0.043(3) Uani 1 1 d . . . H6A H -0.4819 -0.2659 -0.3836 0.052 Uiso 1 1 calc R . . C7 C -0.2954(12) -0.2966(12) -0.3250(9) 0.043(3) Uani 1 1 d . . . H7A H -0.2836 -0.2733 -0.3798 0.051 Uiso 1 1 calc R . . C13 C 0.0246(13) -0.5863(11) -0.1692(10) 0.045(3) Uani 1 1 d . . . H13A H 0.0403 -0.5435 -0.1129 0.054 Uiso 1 1 calc R . . C14 C 0.0285(14) -0.7068(11) -0.1625(12) 0.050(4) Uani 1 1 d . . . H14A H 0.0488 -0.7449 -0.1035 0.060 Uiso 1 1 calc R . . C15 C 0.0000 -0.7724(14) -0.2500 0.034(4) Uani 1 2 d S . . C18 C 0.0349(12) -0.0825(10) -0.3096(9) 0.038(3) Uani 1 1 d . . . H18A H 0.0593 -0.1236 -0.3527 0.045 Uiso 1 1 calc R . . C19 C 0.0363(13) 0.0380(10) -0.3101(9) 0.040(3) Uani 1 1 d . . . H19A H 0.0626 0.0785 -0.3524 0.048 Uiso 1 1 calc R . . C20 C 0.0000 -0.9033(14) -0.2500 0.041(5) Uani 1 2 d S . . O100 O 0.844(2) -0.0947(16) -0.0273(12) 0.132(7) Uani 1 1 d . . . C100 C 0.662(2) -0.040(2) -0.1491(19) 0.114(9) Uani 1 1 d . . . H10A H 0.6797 -0.1058 -0.1815 0.170 Uiso 1 1 calc R . . H10B H 0.6704 0.0325 -0.1797 0.170 Uiso 1 1 calc R . . H10C H 0.5756 -0.0457 -0.1529 0.170 Uiso 1 1 calc R . . C101 C 0.753(2) -0.0387(17) -0.0488(15) 0.072(5) Uani 1 1 d . . . C102 C 0.706(2) 0.031(2) 0.0230(13) 0.103(8) Uani 1 1 d . . . H10D H 0.7561 0.0061 0.0886 0.155 Uiso 1 1 calc R . . H10E H 0.6159 0.0145 0.0057 0.155 Uiso 1 1 calc R . . H10F H 0.7172 0.1147 0.0177 0.155 Uiso 1 1 calc R . . O200 O 0.3544(13) -0.7508(13) -0.0347(8) 0.101(5) Uani 1 1 d . . . C200 C 0.384(3) -0.799(3) -0.169(3) 0.178(17) Uani 1 1 d . . . H20A H 0.3756 -0.8770 -0.1473 0.267 Uiso 1 1 calc R . . H20B H 0.4687 -0.7898 -0.1683 0.267 Uiso 1 1 calc R . . H20C H 0.3193 -0.7871 -0.2335 0.267 Uiso 1 1 calc R . . C201 C 0.3665(17) -0.711(2) -0.1039(14) 0.075(6) Uani 1 1 d . . . C202 C 0.371(3) -0.593(2) -0.1236(18) 0.158(15) Uani 1 1 d . . . H20D H 0.3533 -0.5466 -0.0769 0.237 Uiso 1 1 calc R . . H20E H 0.3062 -0.5756 -0.1875 0.237 Uiso 1 1 calc R . . H20F H 0.4549 -0.5730 -0.1201 0.237 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 0.0215(12) 0.0171(12) 0.0617(17) 0.000 0.0300(11) 0.000 S1 0.081(4) 0.121(5) 0.070(3) 0.043(3) 0.028(3) 0.002(3) N1 0.023(5) 0.025(5) 0.080(8) 0.011(5) 0.037(5) -0.001(4) N3 0.026(5) 0.023(5) 0.062(6) 0.006(4) 0.033(5) 0.002(4) N5 0.023(7) 0.036(9) 0.064(10) 0.000 0.031(7) 0.000 N6 0.041(8) 0.005(7) 0.065(10) 0.000 0.033(7) 0.000 C1 0.031(7) 0.060(9) 0.054(9) 0.010(7) 0.023(7) 0.011(7) C3 0.016(5) 0.060(9) 0.048(7) 0.006(6) 0.023(5) 0.001(5) C4 0.019(6) 0.067(9) 0.061(9) -0.012(7) 0.028(6) -0.007(6) C5 0.025(6) 0.033(6) 0.053(7) -0.002(6) 0.028(5) 0.009(5) C6 0.029(6) 0.054(8) 0.053(8) 0.011(6) 0.023(6) 0.017(6) C7 0.043(7) 0.057(9) 0.042(7) 0.021(6) 0.031(6) 0.021(6) C13 0.054(8) 0.014(6) 0.071(9) 0.005(6) 0.031(7) 0.001(6) C14 0.061(9) 0.010(6) 0.093(11) 0.001(6) 0.045(8) 0.008(6) C15 0.033(9) 0.017(8) 0.068(12) 0.000 0.034(9) 0.000 C18 0.037(7) 0.022(6) 0.062(8) -0.004(5) 0.029(6) -0.003(5) C19 0.049(8) 0.017(6) 0.063(9) -0.005(5) 0.031(7) -0.009(5) C20 0.017(8) 0.014(8) 0.088(14) 0.000 0.019(9) 0.000 O100 0.20(2) 0.118(14) 0.142(15) 0.051(11) 0.138(15) 0.060(14) C100 0.106(18) 0.095(17) 0.18(3) -0.062(17) 0.100(19) -0.050(14) C101 0.081(13) 0.069(12) 0.086(14) 0.022(10) 0.053(11) 0.025(10) C102 0.15(2) 0.085(16) 0.068(13) 0.002(11) 0.043(13) -0.038(15) O200 0.094(10) 0.120(12) 0.048(7) 0.020(7) -0.010(6) -0.058(9) C200 0.17(3) 0.15(3) 0.28(4) 0.15(3) 0.17(3) 0.07(2) C201 0.049(10) 0.099(15) 0.082(13) 0.033(12) 0.031(9) 0.006(10) C202 0.14(2) 0.100(19) 0.121(19) 0.069(16) -0.055(16) -0.062(17) _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 2.133(12) . ? Fe1 N1 2.133(12) 2_554 ? Fe1 N6 2.212(12) . ? Fe1 N5 2.215(15) . ? Fe1 N3 2.240(8) . ? Fe1 N3 2.240(8) 2_554 ? S1 C1 1.640(16) . ? N1 C1 1.136(17) . ? N3 C3 1.304(14) . ? N3 C7 1.362(15) . ? N5 C13 1.356(15) 2_554 ? N5 C13 1.356(15) . ? N6 C18 1.336(13) 2_554 ? N6 C18 1.336(13) . ? C3 C4 1.409(15) . ? C3 H3A 0.9500 . ? C4 C5 1.452(17) . ? C4 H4A 0.9500 . ? C5 C6 1.403(17) . ? C5 C5 1.46(2) 2_454 ? C6 C7 1.345(17) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C13 C14 1.393(19) . ? C13 H13A 0.9500 . ? C14 C15 1.463(17) . ? C14 H14A 0.9500 . ? C15 C14 1.463(17) 2_554 ? C15 C20 1.51(2) . ? C18 C19 1.389(17) . ? C18 H18A 0.9500 . ? C19 C20 1.350(15) 1_565 ? C19 H19A 0.9500 . ? C20 C19 1.350(15) 1_545 ? C20 C19 1.350(15) 2_544 ? O100 C101 1.15(2) . ? C100 C101 1.47(3) . ? C100 H10A 0.9800 . ? C100 H10B 0.9800 . ? C100 H10C 0.9800 . ? C101 C102 1.64(3) . ? C102 H10D 0.9800 . ? C102 H10E 0.9800 . ? C102 H10F 0.9800 . ? O200 C201 1.22(2) . ? C200 C201 1.49(4) . ? C200 H20A 0.9800 . ? C200 H20B 0.9800 . ? C200 H20C 0.9800 . ? C201 C202 1.41(3) . ? C202 H20D 0.9800 . ? C202 H20E 0.9800 . ? C202 H20F 0.9800 . ? 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 N1 179.5(5) . 2_554 ? N1 Fe1 N6 89.7(3) . . ? N1 Fe1 N6 89.7(3) 2_554 . ? N1 Fe1 N5 90.3(3) . . ? N1 Fe1 N5 90.3(3) 2_554 . ? N6 Fe1 N5 180.000(2) . . ? N1 Fe1 N3 89.2(3) . . ? N1 Fe1 N3 90.8(3) 2_554 . ? N6 Fe1 N3 89.3(2) . . ? N5 Fe1 N3 90.7(2) . . ? N1 Fe1 N3 90.8(3) . 2_554 ? N1 Fe1 N3 89.2(3) 2_554 2_554 ? N6 Fe1 N3 89.3(2) . 2_554 ? N5 Fe1 N3 90.7(2) . 2_554 ? N3 Fe1 N3 178.6(5) . 2_554 ? C1 N1 Fe1 166.9(9) . . ? C3 N3 C7 117.3(9) . . ? C3 N3 Fe1 122.8(8) . . ? C7 N3 Fe1 119.9(7) . . ? C13 N5 C13 117.8(16) 2_554 . ? C13 N5 Fe1 121.1(8) 2_554 . ? C13 N5 Fe1 121.1(8) . . ? C18 N6 C18 118.4(14) 2_554 . ? C18 N6 Fe1 120.8(7) 2_554 . ? C18 N6 Fe1 120.8(7) . . ? N1 C1 S1 177.3(14) . . ? N3 C3 C4 126.4(12) . . ? N3 C3 H3A 116.8 . . ? C4 C3 H3A 116.8 . . ? C3 C4 C5 114.8(11) . . ? C3 C4 H4A 122.6 . . ? C5 C4 H4A 122.6 . . ? C6 C5 C4 117.5(10) . . ? C6 C5 C5 123.9(13) . 2_454 ? C4 C5 C5 118.5(12) . 2_454 ? C7 C6 C5 120.8(12) . . ? C7 C6 H6A 119.6 . . ? C5 C6 H6A 119.6 . . ? C6 C7 N3 123.0(11) . . ? C6 C7 H7A 118.5 . . ? N3 C7 H7A 118.5 . . ? N5 C13 C14 124.9(14) . . ? N5 C13 H13A 117.6 . . ? C14 C13 H13A 117.6 . . ? C13 C14 C15 117.3(14) . . ? C13 C14 H14A 121.3 . . ? C15 C14 H14A 121.3 . . ? C14 C15 C14 117.8(16) . 2_554 ? C14 C15 C20 121.1(8) . . ? C14 C15 C20 121.1(8) 2_554 . ? N6 C18 C19 121.6(12) . . ? N6 C18 H18A 119.2 . . ? C19 C18 H18A 119.2 . . ? C20 C19 C18 119.4(12) 1_565 . ? C20 C19 H19A 120.3 1_565 . ? C18 C19 H19A 120.3 . . ? C19 C20 C19 119.7(16) 1_545 2_544 ? C19 C20 C15 120.2(8) 1_545 . ? C19 C20 C15 120.2(8) 2_544 . ? C101 C100 H10A 109.5 . . ? C101 C100 H10B 109.5 . . ? H10A C100 H10B 109.5 . . ? C101 C100 H10C 109.5 . . ? H10A C100 H10C 109.5 . . ? H10B C100 H10C 109.5 . . ? O100 C101 C100 118(2) . . ? O100 C101 C102 127(2) . . ? C100 C101 C102 114.9(17) . . ? C101 C102 H10D 109.5 . . ? C101 C102 H10E 109.5 . . ? H10D C102 H10E 109.5 . . ? C101 C102 H10F 109.5 . . ? H10D C102 H10F 109.5 . . ? H10E C102 H10F 109.5 . . ? C201 C200 H20A 109.5 . . ? C201 C200 H20B 109.5 . . ? H20A C200 H20B 109.5 . . ? C201 C200 H20C 109.5 . . ? H20A C200 H20C 109.5 . . ? H20B C200 H20C 109.5 . . ? O200 C201 C202 125(3) . . ? O200 C201 C200 116(2) . . ? C202 C201 C200 119(2) . . ? C201 C202 H20D 109.5 . . ? C201 C202 H20E 109.5 . . ? H20D C202 H20E 109.5 . . ? C201 C202 H20F 109.5 . . ? H20D C202 H20F 109.5 . . ? H20E C202 H20F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 2.168 _refine_diff_density_min -2.838 _refine_diff_density_rms 0.217 #===END data_1-3methanol _database_code_depnum_ccdc_archive 'CCDC 771546' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H28 Fe1 N6 O3 S2' _chemical_formula_weight 592.41 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.049(2) _cell_length_b 16.613(3) _cell_length_c 12.5984(18) _cell_angle_alpha 90.00 _cell_angle_beta 120.581(4) _cell_angle_gamma 90.00 _cell_volume 2891.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2452 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.69 _exptl_crystal_description Prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.702 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12028 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.70 _reflns_number_total 3324 _reflns_number_gt 2875 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0870P)^2^+9.0150P] 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 3324 _refine_ls_number_parameters 192 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1517 _refine_ls_wR_factor_gt 0.1446 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.062 _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 0.5000 0.25669(3) 0.2500 0.01198(17) Uani 1 2 d S . . N1 N 0.41927(15) 0.26179(12) 0.0543(2) 0.0165(4) Uani 1 1 d . . . C1 C 0.40588(18) 0.27246(15) -0.0446(2) 0.0178(5) Uani 1 1 d . . . S1 S 0.38727(7) 0.28765(5) -0.18296(7) 0.0360(2) Uani 1 1 d . . . N3 N 0.40577(14) 0.15907(12) 0.25403(19) 0.0151(4) Uani 1 1 d . . . C3 C 0.42115(19) 0.12340(16) 0.3582(2) 0.0208(5) Uani 1 1 d . . . H3A H 0.4745 0.1410 0.4344 0.025 Uiso 1 1 calc R . . C4 C 0.36323(19) 0.06234(16) 0.3603(2) 0.0217(5) Uani 1 1 d . . . H4A H 0.3777 0.0384 0.4362 0.026 Uiso 1 1 calc R . . C5 C 0.28377(17) 0.03641(14) 0.2502(2) 0.0171(5) Uani 1 1 d . . . C6 C 0.26796(18) 0.07250(16) 0.1419(3) 0.0213(5) Uani 1 1 d . . . H6A H 0.2150 0.0563 0.0645 0.026 Uiso 1 1 calc R . . C7 C 0.33053(18) 0.13236(15) 0.1483(2) 0.0190(5) Uani 1 1 d . . . H7A H 0.3194 0.1558 0.0733 0.023 Uiso 1 1 calc R . . N4 N 0.09508(14) -0.14805(12) 0.24493(19) 0.0155(4) Uani 1 1 d . . . C8 C 0.19171(17) -0.15447(15) 0.3154(2) 0.0173(5) Uani 1 1 d . . . H8A H 0.2178 -0.2013 0.3647 0.021 Uiso 1 1 calc R . . C9 C 0.25523(18) -0.09635(15) 0.3201(2) 0.0189(5) Uani 1 1 d . . . H9A H 0.3231 -0.1035 0.3716 0.023 Uiso 1 1 calc R . . C10 C 0.21861(18) -0.02721(15) 0.2484(2) 0.0175(5) Uani 1 1 d . . . C11 C 0.11819(18) -0.02024(16) 0.1742(3) 0.0219(6) Uani 1 1 d . . . H11A H 0.0902 0.0258 0.1236 0.026 Uiso 1 1 calc R . . C12 C 0.06011(18) -0.08132(15) 0.1754(3) 0.0206(5) Uani 1 1 d . . . H12A H -0.0081 -0.0759 0.1245 0.025 Uiso 1 1 calc R . . C200 C -0.0093(4) 0.3882(3) 0.3466(5) 0.0701(14) Uani 1 1 d . . . O200 O 0.0000 0.4260(4) 0.2500 0.111(2) Uani 1 2 d S . . O60 O 0.3490(4) 0.2872(3) 0.4878(5) 0.0588(16) Uani 0.595(6) 1 d PD A 1 C60 C 0.3359(7) 0.3653(5) 0.5266(7) 0.074(3) Uani 0.595(6) 1 d PD A 1 C50 C 0.2847(11) 0.4059(6) 0.5237(11) 0.067(4) Uani 0.405(6) 1 d PD A 2 O50 O 0.3735(7) 0.4400(4) 0.5815(6) 0.059(2) Uani 0.405(6) 1 d PD 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 0.0116(3) 0.0105(2) 0.0160(3) 0.000 0.0085(2) 0.000 N1 0.0142(10) 0.0159(9) 0.0207(11) 0.0010(8) 0.0098(9) 0.0001(7) C1 0.0176(11) 0.0134(10) 0.0229(13) -0.0009(9) 0.0107(10) -0.0004(9) S1 0.0520(5) 0.0381(5) 0.0235(4) 0.0032(3) 0.0234(4) 0.0002(4) N3 0.0147(9) 0.0130(9) 0.0212(11) 0.0001(8) 0.0117(8) -0.0005(7) C3 0.0207(12) 0.0207(12) 0.0204(12) -0.0010(10) 0.0100(10) -0.0069(10) C4 0.0227(12) 0.0223(13) 0.0204(13) 0.0028(10) 0.0112(11) -0.0053(10) C5 0.0153(11) 0.0135(11) 0.0249(13) 0.0005(9) 0.0119(10) -0.0014(9) C6 0.0183(12) 0.0208(12) 0.0220(13) 0.0002(10) 0.0083(10) -0.0051(10) C7 0.0192(12) 0.0185(12) 0.0202(12) 0.0011(9) 0.0107(10) -0.0029(9) N4 0.0144(9) 0.0147(9) 0.0201(10) -0.0001(8) 0.0106(8) -0.0016(7) C8 0.0150(11) 0.0161(11) 0.0203(12) 0.0026(9) 0.0086(9) -0.0007(9) C9 0.0139(11) 0.0203(12) 0.0215(12) 0.0013(10) 0.0082(10) -0.0013(9) C10 0.0171(11) 0.0165(11) 0.0209(12) -0.0007(9) 0.0111(10) -0.0036(9) C11 0.0187(12) 0.0174(12) 0.0293(14) 0.0073(10) 0.0118(11) -0.0001(9) C12 0.0142(11) 0.0196(12) 0.0267(13) 0.0052(10) 0.0093(10) 0.0002(9) C200 0.087(4) 0.063(3) 0.057(3) -0.001(2) 0.034(3) -0.014(3) O200 0.166(7) 0.085(4) 0.137(6) 0.000 0.117(6) 0.000 O60 0.049(3) 0.075(4) 0.048(3) 0.009(3) 0.022(2) -0.001(3) C60 0.145(8) 0.072(5) 0.058(4) 0.058(4) 0.090(5) 0.083(6) C50 0.138(12) 0.039(6) 0.060(7) 0.009(5) 0.078(8) -0.006(7) O50 0.105(7) 0.043(4) 0.041(4) 0.014(3) 0.046(4) 0.017(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 Fe1 N1 2.125(2) . ? Fe1 N1 2.125(2) 2_655 ? Fe1 N4 2.222(2) 3 ? Fe1 N4 2.222(2) 4 ? Fe1 N3 2.236(2) 2_655 ? Fe1 N3 2.236(2) . ? N1 C1 1.165(4) . ? C1 S1 1.631(3) . ? N3 C7 1.339(3) . ? N3 C3 1.344(3) . ? C3 C4 1.385(3) . ? C4 C5 1.391(4) . ? C5 C6 1.391(4) . ? C5 C10 1.479(3) . ? C6 C7 1.386(3) . ? N4 C8 1.343(3) . ? N4 C12 1.346(3) . ? N4 Fe1 2.222(2) 3_445 ? C8 C9 1.384(3) . ? C9 C10 1.393(4) . ? C10 C11 1.397(4) . ? C11 C12 1.383(3) . ? C200 O200 1.444(6) . ? O200 C200 1.444(6) 2 ? O60 C60 1.439(9) . ? C50 O50 1.352(13) . ? 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 N1 175.43(11) . 2_655 ? N1 Fe1 N4 87.74(8) . 3 ? N1 Fe1 N4 89.01(8) 2_655 3 ? N1 Fe1 N4 89.01(8) . 4 ? N1 Fe1 N4 87.74(8) 2_655 4 ? N4 Fe1 N4 89.15(10) 3 4 ? N1 Fe1 N3 91.30(8) . 2_655 ? N1 Fe1 N3 92.01(8) 2_655 2_655 ? N4 Fe1 N3 91.93(8) 3 2_655 ? N4 Fe1 N3 178.88(7) 4 2_655 ? N1 Fe1 N3 92.01(8) . . ? N1 Fe1 N3 91.30(8) 2_655 . ? N4 Fe1 N3 178.88(7) 3 . ? N4 Fe1 N3 91.93(8) 4 . ? N3 Fe1 N3 86.99(10) 2_655 . ? C1 N1 Fe1 156.8(2) . . ? N1 C1 S1 179.8(3) . . ? C7 N3 C3 116.8(2) . . ? C7 N3 Fe1 119.72(16) . . ? C3 N3 Fe1 123.50(16) . . ? N3 C3 C4 123.4(2) . . ? C3 C4 C5 119.5(2) . . ? C6 C5 C4 117.5(2) . . ? C6 C5 C10 121.2(2) . . ? C4 C5 C10 121.3(2) . . ? C7 C6 C5 119.2(2) . . ? N3 C7 C6 123.7(2) . . ? C8 N4 C12 117.0(2) . . ? C8 N4 Fe1 120.22(16) . 3_445 ? C12 N4 Fe1 122.71(16) . 3_445 ? N4 C8 C9 123.4(2) . . ? C8 C9 C10 119.3(2) . . ? C9 C10 C11 117.7(2) . . ? C9 C10 C5 121.2(2) . . ? C11 C10 C5 121.2(2) . . ? C12 C11 C10 119.1(2) . . ? N4 C12 C11 123.5(2) . . ? C200 O200 C200 128.3(7) . 2 ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.70 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.026 _refine_diff_density_min -0.854 _refine_diff_density_rms 0.101 #===END data_1-2nitromethane-1methanol _database_code_depnum_ccdc_archive 'CCDC 771547' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 Fe N8 O5 S2' _chemical_formula_weight 640.49 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.4191(6) _cell_length_b 16.3755(6) _cell_length_c 12.5505(4) _cell_angle_alpha 90.00 _cell_angle_beta 120.210(2) _cell_angle_gamma 90.00 _cell_volume 2916.17(18) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 5503 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.48 _exptl_crystal_description Prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.710 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 12669 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3346 _reflns_number_gt 2965 _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^)+(0.0605P)^2^+6.0500P] 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 3346 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.5000 0.26792(2) 0.2500 0.01592(13) Uani 1 2 d S . . N1 N 0.42307(13) 0.27294(10) 0.05424(17) 0.0233(4) Uani 1 1 d . . . C1 C 0.39999(14) 0.27384(12) -0.0497(2) 0.0217(4) Uani 1 1 d . . . S1 S 0.36772(5) 0.27417(5) -0.19556(6) 0.04289(19) Uani 1 1 d . . . N3 N 0.40734(11) 0.16796(10) 0.25398(16) 0.0206(3) Uani 1 1 d . . . C3 C 0.41946(15) 0.13361(14) 0.3583(2) 0.0283(5) Uani 1 1 d . . . H3A H 0.4704 0.1521 0.4346 0.034 Uiso 1 1 calc R . . C4 C 0.36192(16) 0.07284(14) 0.3607(2) 0.0291(5) Uani 1 1 d . . . H4A H 0.3745 0.0497 0.4369 0.035 Uiso 1 1 calc R . . C5 C 0.28547(14) 0.04583(12) 0.2507(2) 0.0233(4) Uani 1 1 d . . . C6 C 0.27308(15) 0.08000(14) 0.1420(2) 0.0272(4) Uani 1 1 d . . . H6A H 0.2226 0.0627 0.0645 0.033 Uiso 1 1 calc R . . C7 C 0.33511(15) 0.13953(13) 0.1481(2) 0.0257(4) Uani 1 1 d . . . H7A H 0.3260 0.1616 0.0729 0.031 Uiso 1 1 calc R . . N4 N 0.09519(11) -0.13522(10) 0.24738(15) 0.0204(3) Uani 1 1 d . . . C8 C 0.18887(14) -0.14352(13) 0.3181(2) 0.0243(4) Uani 1 1 d . . . H8A H 0.2128 -0.1909 0.3681 0.029 Uiso 1 1 calc R . . C9 C 0.25261(14) -0.08633(13) 0.3218(2) 0.0258(4) Uani 1 1 d . . . H9A H 0.3184 -0.0948 0.3736 0.031 Uiso 1 1 calc R . . C10 C 0.21949(14) -0.01676(12) 0.24922(19) 0.0228(4) Uani 1 1 d . . . C11 C 0.12191(15) -0.00779(13) 0.1750(2) 0.0262(4) Uani 1 1 d . . . H11A H 0.0961 0.0387 0.1235 0.031 Uiso 1 1 calc R . . C12 C 0.06336(14) -0.06786(13) 0.1777(2) 0.0246(4) Uani 1 1 d . . . H12A H -0.0028 -0.0608 0.1275 0.029 Uiso 1 1 calc R . . C100 C 0.3654(2) 0.3019(2) 0.5104(3) 0.0536(7) Uani 1 1 d . . . H10A H 0.3379 0.2570 0.5334 0.080 Uiso 1 1 calc R . . H10B H 0.4342 0.3011 0.5635 0.080 Uiso 1 1 calc R . . H10C H 0.3489 0.2956 0.4242 0.080 Uiso 1 1 calc R . . N100 N 0.32853(18) 0.38016(16) 0.5257(2) 0.0465(6) Uani 1 1 d . . . O100 O 0.3827(2) 0.43695(16) 0.5747(2) 0.0751(8) Uani 1 1 d . . . O101 O 0.24484(18) 0.38455(18) 0.4866(3) 0.0786(8) Uani 1 1 d . . . O200 O 0.0000 0.4351(5) 0.2500 0.136(2) Uani 1 2 d S . . C200 C 0.0176(5) 0.3975(4) 0.1566(5) 0.0522(15) Uani 0.50 1 d P . . H20A H 0.0641 0.3537 0.1947 0.078 Uiso 0.50 1 calc PR . . H20B H 0.0418 0.4390 0.1233 0.078 Uiso 0.50 1 calc PR . . H20C H -0.0413 0.3750 0.0897 0.078 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 Fe1 0.0148(2) 0.0144(2) 0.0200(2) 0.000 0.00981(16) 0.000 N1 0.0223(8) 0.0223(9) 0.0255(9) 0.0021(7) 0.0123(7) 0.0014(7) C1 0.0198(9) 0.0188(9) 0.0273(10) 0.0010(8) 0.0124(8) -0.0008(7) S1 0.0527(4) 0.0521(4) 0.0254(3) -0.0022(3) 0.0208(3) -0.0069(3) N3 0.0187(8) 0.0182(8) 0.0268(9) 0.0002(7) 0.0129(7) -0.0019(6) C3 0.0252(10) 0.0309(11) 0.0255(10) -0.0012(9) 0.0103(9) -0.0099(9) C4 0.0302(11) 0.0313(11) 0.0252(10) 0.0031(9) 0.0136(9) -0.0087(9) C5 0.0218(9) 0.0197(9) 0.0307(11) -0.0003(8) 0.0149(9) -0.0036(8) C6 0.0258(10) 0.0272(11) 0.0256(10) -0.0011(8) 0.0106(9) -0.0085(8) C7 0.0277(10) 0.0255(10) 0.0247(10) 0.0004(8) 0.0137(9) -0.0067(8) N4 0.0193(8) 0.0188(8) 0.0246(8) -0.0005(6) 0.0121(7) -0.0032(6) C8 0.0206(9) 0.0209(9) 0.0293(10) 0.0048(8) 0.0110(8) -0.0015(8) C9 0.0179(9) 0.0264(10) 0.0304(11) 0.0041(8) 0.0102(8) -0.0028(8) C10 0.0232(10) 0.0210(9) 0.0270(10) -0.0013(8) 0.0148(8) -0.0054(8) C11 0.0236(10) 0.0218(10) 0.0314(11) 0.0057(8) 0.0125(9) -0.0007(8) C12 0.0196(9) 0.0229(10) 0.0306(10) 0.0028(8) 0.0122(8) -0.0008(8) C100 0.0531(18) 0.0559(18) 0.064(2) 0.0022(16) 0.0383(16) 0.0049(15) N100 0.0558(15) 0.0497(14) 0.0440(13) 0.0071(11) 0.0326(12) 0.0012(12) O100 0.100(2) 0.0588(15) 0.0615(15) -0.0081(12) 0.0373(15) -0.0234(15) O101 0.0631(16) 0.0774(17) 0.112(2) 0.0159(17) 0.0566(17) 0.0180(14) O200 0.108(4) 0.162(6) 0.144(5) 0.000 0.069(4) 0.000 C200 0.059(4) 0.057(4) 0.033(3) 0.003(3) 0.018(3) 0.022(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 2.1250(18) . ? Fe1 N1 2.1250(18) 2_655 ? Fe1 N4 2.2387(16) 4 ? Fe1 N4 2.2387(16) 3 ? Fe1 N3 2.2523(16) . ? Fe1 N3 2.2523(16) 2_655 ? N1 C1 1.161(3) . ? C1 S1 1.630(2) . ? N3 C7 1.343(3) . ? N3 C3 1.345(3) . ? C3 C4 1.383(3) . ? C4 C5 1.391(3) . ? C5 C6 1.391(3) . ? C5 C10 1.485(3) . ? C6 C7 1.384(3) . ? N4 C12 1.340(3) . ? N4 C8 1.341(3) . ? N4 Fe1 2.2387(16) 3_445 ? C8 C9 1.388(3) . ? C9 C10 1.387(3) . ? C10 C11 1.398(3) . ? C11 C12 1.388(3) . ? C100 N100 1.471(4) . ? N100 O101 1.206(3) . ? N100 O100 1.218(3) . ? O200 C200 1.476(6) 2 ? O200 C200 1.476(6) . ? 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 N1 175.57(9) . 2_655 ? N1 Fe1 N4 88.64(6) . 4 ? N1 Fe1 N4 88.22(6) 2_655 4 ? N1 Fe1 N4 88.21(6) . 3 ? N1 Fe1 N4 88.64(6) 2_655 3 ? N4 Fe1 N4 89.77(9) 4 3 ? N1 Fe1 N3 92.21(6) . . ? N1 Fe1 N3 91.01(6) 2_655 . ? N4 Fe1 N3 91.73(6) 4 . ? N4 Fe1 N3 178.45(6) 3 . ? N1 Fe1 N3 91.01(6) . 2_655 ? N1 Fe1 N3 92.21(6) 2_655 2_655 ? N4 Fe1 N3 178.45(6) 4 2_655 ? N4 Fe1 N3 91.73(6) 3 2_655 ? N3 Fe1 N3 86.77(8) . 2_655 ? C1 N1 Fe1 165.38(16) . . ? N1 C1 S1 179.4(2) . . ? C7 N3 C3 116.27(17) . . ? C7 N3 Fe1 120.02(13) . . ? C3 N3 Fe1 123.71(14) . . ? N3 C3 C4 123.6(2) . . ? C3 C4 C5 119.5(2) . . ? C4 C5 C6 117.34(19) . . ? C4 C5 C10 121.34(19) . . ? C6 C5 C10 121.32(19) . . ? C7 C6 C5 119.2(2) . . ? N3 C7 C6 123.9(2) . . ? C12 N4 C8 117.15(17) . . ? C12 N4 Fe1 123.17(13) . 3_445 ? C8 N4 Fe1 119.68(13) . 3_445 ? N4 C8 C9 123.25(19) . . ? C10 C9 C8 119.50(19) . . ? C9 C10 C11 117.56(18) . . ? C9 C10 C5 121.08(19) . . ? C11 C10 C5 121.35(19) . . ? C12 C11 C10 119.03(19) . . ? N4 C12 C11 123.51(19) . . ? O101 N100 O100 123.6(3) . . ? O101 N100 C100 117.3(3) . . ? O100 N100 C100 119.1(3) . . ? C200 O200 C200 130.7(8) 2 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Fe1 N1 C1 95.6(6) 2_655 . . . ? N4 Fe1 N1 C1 140.5(6) 4 . . . ? N4 Fe1 N1 C1 50.7(6) 3 . . . ? N3 Fe1 N1 C1 -127.8(6) . . . . ? N3 Fe1 N1 C1 -41.0(6) 2_655 . . . ? Fe1 N1 C1 S1 77(20) . . . . ? N1 Fe1 N3 C7 -0.73(16) . . . . ? N1 Fe1 N3 C7 176.22(16) 2_655 . . . ? N4 Fe1 N3 C7 87.98(16) 4 . . . ? N4 Fe1 N3 C7 -107(2) 3 . . . ? N3 Fe1 N3 C7 -91.62(16) 2_655 . . . ? N1 Fe1 N3 C3 179.38(17) . . . . ? N1 Fe1 N3 C3 -3.66(17) 2_655 . . . ? N4 Fe1 N3 C3 -91.91(17) 4 . . . ? N4 Fe1 N3 C3 73(2) 3 . . . ? N3 Fe1 N3 C3 88.50(17) 2_655 . . . ? C7 N3 C3 C4 -0.6(3) . . . . ? Fe1 N3 C3 C4 179.30(18) . . . . ? N3 C3 C4 C5 -1.5(4) . . . . ? C3 C4 C5 C6 2.4(3) . . . . ? C3 C4 C5 C10 -177.4(2) . . . . ? C4 C5 C6 C7 -1.3(3) . . . . ? C10 C5 C6 C7 178.5(2) . . . . ? C3 N3 C7 C6 1.8(3) . . . . ? Fe1 N3 C7 C6 -178.10(17) . . . . ? C5 C6 C7 N3 -0.9(4) . . . . ? C12 N4 C8 C9 0.0(3) . . . . ? Fe1 N4 C8 C9 -179.98(17) 3_445 . . . ? N4 C8 C9 C10 -0.2(3) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? C8 C9 C10 C5 180.0(2) . . . . ? C4 C5 C10 C9 -44.8(3) . . . . ? C6 C5 C10 C9 135.4(2) . . . . ? C4 C5 C10 C11 135.1(2) . . . . ? C6 C5 C10 C11 -44.7(3) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C5 C10 C11 C12 -179.6(2) . . . . ? C8 N4 C12 C11 0.4(3) . . . . ? Fe1 N4 C12 C11 -179.61(16) 3_445 . . . ? C10 C11 C12 N4 -0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.895 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.069 #===END #===END data_1.3CS2 _database_code_depnum_ccdc_archive 'CCDC 775642' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H16 Fe N6 S8' _chemical_formula_weight 712.77 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' S S 0.1246 0.1234 '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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.5305(5) _cell_length_b 11.5424(5) _cell_length_c 12.7461(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.832(2) _cell_angle_gamma 90.00 _cell_volume 1585.48(12) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 2248 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.02 _exptl_crystal_description Prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 1.029 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8609 _exptl_absorpt_correction_T_max 0.9503 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16404 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 30.05 _reflns_number_total 4617 _reflns_number_gt 3842 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0718P)^2^+1.2180P] 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 4617 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1430 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _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 0.0000 0.28290(3) 0.2500 0.01584(12) Uani 1 2 d S . . N1 N -0.06780(18) 0.28025(16) 0.07254(17) 0.0230(4) Uani 1 1 d . . . C1 C -0.1444(2) 0.3004(2) -0.0136(2) 0.0246(4) Uani 1 1 d . . . S1 S -0.25347(9) 0.32872(10) -0.13189(7) 0.0583(3) Uani 1 1 d . . . N3 N -0.19356(16) 0.28330(16) 0.24793(16) 0.0203(4) Uani 1 1 d . . . C3 C -0.2204(2) 0.3337(2) 0.3310(2) 0.0287(5) Uani 1 1 d . . . H3A H -0.1556 0.3709 0.3894 0.034 Uiso 1 1 calc R . . C4 C -0.3394(2) 0.3340(3) 0.3356(2) 0.0329(6) Uani 1 1 d . . . H4A H -0.3541 0.3690 0.3972 0.039 Uiso 1 1 calc R . . C5 C -0.4357(2) 0.2831(2) 0.2499(2) 0.0238(4) Uani 1 1 d . . . C6 C -0.4081(2) 0.2335(2) 0.1623(2) 0.0323(6) Uani 1 1 d . . . H6A H -0.4719 0.1993 0.1007 0.039 Uiso 1 1 calc R . . C7 C -0.2870(2) 0.2343(2) 0.1657(2) 0.0300(5) Uani 1 1 d . . . H7A H -0.2693 0.1979 0.1061 0.036 Uiso 1 1 calc R . . N5 N 0.0000 0.0896(2) 0.2500 0.0199(5) Uani 1 2 d S . . C13 C 0.0151(2) 0.02948(19) 0.1663(2) 0.0263(5) Uani 1 1 d . . . H13A H 0.0268 0.0711 0.1065 0.032 Uiso 1 1 calc R . . C14 C 0.0146(3) -0.0905(2) 0.1622(2) 0.0279(5) Uani 1 1 d . . . H14A H 0.0241 -0.1296 0.1001 0.034 Uiso 1 1 calc R . . C15 C 0.0000 -0.1532(3) 0.2500 0.0217(6) Uani 1 2 d S . . N6 N 0.0000 -0.5235(2) 0.2500 0.0212(5) Uani 1 2 d S . . C18 C -0.0721(3) -0.4632(2) 0.1612(2) 0.0298(5) Uani 1 1 d . . . H18A H -0.1246 -0.5047 0.0977 0.036 Uiso 1 1 calc R . . C19 C -0.0741(3) -0.3428(2) 0.1573(2) 0.0312(5) Uani 1 1 d . . . H19A H -0.1255 -0.3033 0.0920 0.037 Uiso 1 1 calc R . . C20 C 0.0000 -0.2817(3) 0.2500 0.0228(6) Uani 1 2 d S . . C100 C -0.3209(3) -0.0516(3) 0.0165(4) 0.0571(10) Uani 1 1 d . . . S2 S -0.30366(15) 0.00558(14) -0.08446(13) 0.0893(4) Uani 1 1 d . . . S3 S -0.33735(12) -0.10873(12) 0.11948(11) 0.0755(3) Uani 1 1 d . . . C200 C -0.5000 0.5000 0.0000 0.0427(10) Uani 1 2 d S . . S4 S -0.41655(11) 0.56073(10) 0.10722(8) 0.0666(3) 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 Fe1 0.0140(2) 0.01345(19) 0.0216(2) 0.000 0.00823(16) 0.000 N1 0.0238(9) 0.0207(9) 0.0263(10) -0.0015(7) 0.0111(8) -0.0002(7) C1 0.0281(11) 0.0214(10) 0.0271(11) -0.0002(8) 0.0132(9) 0.0029(8) S1 0.0496(5) 0.0775(7) 0.0339(4) 0.0112(4) -0.0021(4) 0.0187(4) N3 0.0157(8) 0.0208(8) 0.0271(9) -0.0019(7) 0.0108(7) -0.0001(6) C3 0.0170(10) 0.0390(13) 0.0309(12) -0.0118(10) 0.0094(9) -0.0028(9) C4 0.0202(11) 0.0490(15) 0.0330(13) -0.0131(11) 0.0136(10) -0.0017(10) C5 0.0156(10) 0.0275(11) 0.0302(12) 0.0017(9) 0.0107(9) -0.0006(8) C6 0.0198(11) 0.0422(15) 0.0366(14) -0.0137(11) 0.0121(10) -0.0096(10) C7 0.0236(11) 0.0366(13) 0.0349(13) -0.0150(10) 0.0166(10) -0.0089(9) N5 0.0232(12) 0.0135(11) 0.0258(13) 0.000 0.0120(11) 0.000 C13 0.0421(14) 0.0164(10) 0.0268(11) 0.0035(8) 0.0203(10) 0.0043(9) C14 0.0456(14) 0.0167(10) 0.0268(11) 0.0001(8) 0.0195(11) 0.0051(9) C15 0.0262(15) 0.0145(13) 0.0242(15) 0.000 0.0089(12) 0.000 N6 0.0204(12) 0.0150(11) 0.0295(14) 0.000 0.0104(11) 0.000 C18 0.0356(13) 0.0163(10) 0.0311(12) -0.0034(9) 0.0042(10) 0.0023(9) C19 0.0400(14) 0.0179(11) 0.0290(12) 0.0001(9) 0.0040(10) 0.0053(9) C20 0.0280(15) 0.0154(13) 0.0265(15) 0.000 0.0116(13) 0.000 C100 0.0409(18) 0.054(2) 0.066(2) -0.0224(18) 0.0056(16) -0.0046(15) S2 0.0945(10) 0.0919(10) 0.0852(9) -0.0077(7) 0.0363(8) -0.0274(8) S3 0.0709(7) 0.0827(8) 0.0638(7) -0.0040(6) 0.0128(6) -0.0077(6) C200 0.040(2) 0.047(2) 0.040(2) 0.0096(18) 0.0122(18) -0.0088(18) S4 0.0777(7) 0.0678(7) 0.0430(5) -0.0024(4) 0.0076(5) -0.0291(5) _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 2.114(2) . ? Fe1 N1 2.114(2) 2 ? Fe1 N3 2.2225(17) 2 ? Fe1 N3 2.2226(17) . ? Fe1 N5 2.231(3) . ? Fe1 N6 2.235(3) 1_565 ? N1 C1 1.162(3) . ? C1 S1 1.617(3) . ? N3 C7 1.333(3) . ? N3 C3 1.337(3) . ? C3 C4 1.394(3) . ? C4 C5 1.381(3) . ? C5 C6 1.389(3) . ? C5 C5 1.484(4) 2_455 ? C6 C7 1.383(3) . ? N5 C13 1.335(3) . ? N5 C13 1.335(3) 2 ? C13 C14 1.386(3) . ? C14 C15 1.392(3) . ? C15 C14 1.392(3) 2 ? C15 C20 1.483(4) . ? N6 C18 1.337(3) 2 ? N6 C18 1.337(3) . ? N6 Fe1 2.235(3) 1_545 ? C18 C19 1.391(3) . ? C19 C20 1.380(3) . ? C20 C19 1.380(3) 2 ? C100 S2 1.521(5) . ? C100 S3 1.540(5) . ? C200 S4 1.5328(10) . ? C200 S4 1.5329(10) 3_465 ? 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 N1 178.34(10) . 2 ? N1 Fe1 N3 90.03(7) . 2 ? N1 Fe1 N3 89.98(7) 2 2 ? N1 Fe1 N3 89.98(7) . . ? N1 Fe1 N3 90.02(7) 2 . ? N3 Fe1 N3 179.76(10) 2 . ? N1 Fe1 N5 89.17(5) . . ? N1 Fe1 N5 89.17(5) 2 . ? N3 Fe1 N5 90.12(5) 2 . ? N3 Fe1 N5 90.12(5) . . ? N1 Fe1 N6 90.83(5) . 1_565 ? N1 Fe1 N6 90.83(5) 2 1_565 ? N3 Fe1 N6 89.88(5) 2 1_565 ? N3 Fe1 N6 89.88(5) . 1_565 ? N5 Fe1 N6 180.0 . 1_565 ? C1 N1 Fe1 151.14(18) . . ? N1 C1 S1 178.5(2) . . ? C7 N3 C3 117.22(19) . . ? C7 N3 Fe1 122.38(15) . . ? C3 N3 Fe1 120.40(15) . . ? N3 C3 C4 122.9(2) . . ? C5 C4 C3 119.5(2) . . ? C4 C5 C6 117.5(2) . . ? C4 C5 C5 121.5(2) . 2_455 ? C6 C5 C5 121.0(2) . 2_455 ? C7 C6 C5 119.3(2) . . ? N3 C7 C6 123.5(2) . . ? C13 N5 C13 117.4(3) . 2 ? C13 N5 Fe1 121.30(13) . . ? C13 N5 Fe1 121.30(13) 2 . ? N5 C13 C14 123.3(2) . . ? C13 C14 C15 119.3(2) . . ? C14 C15 C14 117.4(3) . 2 ? C14 C15 C20 121.29(14) . . ? C14 C15 C20 121.29(14) 2 . ? C18 N6 C18 117.2(3) 2 . ? C18 N6 Fe1 121.38(14) 2 1_545 ? C18 N6 Fe1 121.38(14) . 1_545 ? N6 C18 C19 123.2(2) . . ? C20 C19 C18 118.9(2) . . ? C19 C20 C19 118.5(3) . 2 ? C19 C20 C15 120.74(15) . . ? C19 C20 C15 120.74(15) 2 . ? S2 C100 S3 179.4(3) . . ? S4 C200 S4 180.0 . 3_465 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.619 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.088