# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jan Reedijk' _publ_contact_author_email REEDIJK@CHEM.LEIDENUNIV.NL _publ_section_title ; Synthesis and Characterization Studies of a Two-Step Spin-Crossover Mononuclear Iron(II) complex with a [HS-LS-LS] Intermediate Phase ; loop_ _publ_author_name 'Jan Reedijk' 'Sylvestre Bonnet' 'Azzedine Bousseksou' 'Jose Sanchez Costa' 'Patrick Gamez' 'Gabor Molnar' ; M.A.Siegler ; 'Anthony L Spek' # Attachment 'B811746B_ccdc_694533_694535_cif.txt' data_phaseI _database_code_depnum_ccdc_archive 'CCDC 694533' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 Fe N8 S2' _chemical_formula_sum 'C22 H16 Fe N8 S2' _chemical_formula_weight 512.40 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 15.9263(4) _cell_length_b 10.9683(4) _cell_length_c 14.2723(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.457(1) _cell_angle_gamma 90.00 _cell_volume 2212.31(11) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8085 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.49 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.899 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.713 _exptl_absorpt_correction_T_max 0.849 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14693 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.48 _reflns_number_total 2281 _reflns_number_gt 1916 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'PEAKREF (Schreurs, 2005)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'DIRDIF99 (Beurskens et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0368P)^2^+1.6662P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2281 _refine_ls_number_parameters 153 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.51002(3) 0.2500 0.03617(13) Uani 1 2 d S . . C1 C 0.49527(15) 0.73044(19) 0.37123(17) 0.0506(5) Uani 1 1 d . . . H1 H 0.5447 0.7502 0.3564 0.061 Uiso 1 1 calc R . . C2 C 0.46346(15) 0.8183(2) 0.41426(18) 0.0557(5) Uani 1 1 d . . . H2 H 0.4897 0.8960 0.4275 0.067 Uiso 1 1 calc R . . C3 C 0.39107(16) 0.7886(2) 0.43775(19) 0.0575(6) Uani 1 1 d . . . H3 H 0.3667 0.8467 0.4660 0.069 Uiso 1 1 calc R . . C4 C 0.35592(16) 0.6734(2) 0.41919(18) 0.0536(5) Uani 1 1 d . . . H4 H 0.3081 0.6515 0.4361 0.064 Uiso 1 1 calc R . . C5 C 0.39189(13) 0.58841(18) 0.37468(15) 0.0410(4) Uani 1 1 d . . . C6 C 0.38090(13) 0.36337(18) 0.33326(14) 0.0417(4) Uani 1 1 d . . . C7 C 0.33614(16) 0.2591(2) 0.34497(17) 0.0535(5) Uani 1 1 d . . . H7 H 0.2920 0.2650 0.3703 0.064 Uiso 1 1 calc R . . C8 C 0.35806(17) 0.1496(2) 0.31890(18) 0.0595(6) Uani 1 1 d . . . H8 H 0.3291 0.0792 0.3264 0.071 Uiso 1 1 calc R . . C9 C 0.42356(16) 0.14269(19) 0.28113(17) 0.0544(5) Uani 1 1 d . . . H9 H 0.4391 0.0678 0.2626 0.065 Uiso 1 1 calc R . . C10 C 0.46548(14) 0.24770(17) 0.27128(14) 0.0415(4) Uani 1 1 d . . . C11 C 0.28677(13) 0.54379(17) 0.05235(15) 0.0388(4) Uani 1 1 d . . . N1 N 0.45983(11) 0.61687(14) 0.34881(12) 0.0414(4) Uani 1 1 d . . . N2 N 0.35431(13) 0.47284(16) 0.35788(15) 0.0492(4) Uani 1 1 d D . . H2A H 0.3123(14) 0.465(2) 0.3775(18) 0.059 Uiso 1 1 d D . . N3 N 0.44543(10) 0.35805(14) 0.29819(11) 0.0380(3) Uani 1 1 d . . . N4 N 0.35780(12) 0.53105(17) 0.12619(14) 0.0519(4) Uani 1 1 d . . . S1 S 0.18769(4) 0.55854(6) -0.05538(4) 0.05713(18) 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 0.0374(2) 0.0374(2) 0.0382(2) 0.000 0.02126(16) 0.000 C1 0.0481(11) 0.0476(12) 0.0637(13) -0.0117(10) 0.0323(10) -0.0120(9) C2 0.0586(13) 0.0424(12) 0.0714(15) -0.0142(11) 0.0343(12) -0.0093(10) C3 0.0642(14) 0.0512(13) 0.0682(14) -0.0110(11) 0.0401(12) 0.0023(11) C4 0.0578(12) 0.0544(13) 0.0651(14) -0.0053(11) 0.0424(11) -0.0030(10) C5 0.0428(10) 0.0431(10) 0.0404(10) -0.0017(8) 0.0221(8) -0.0036(8) C6 0.0471(11) 0.0421(11) 0.0382(10) -0.0016(8) 0.0217(9) -0.0083(9) C7 0.0604(13) 0.0527(13) 0.0566(13) -0.0005(10) 0.0349(11) -0.0138(10) C8 0.0744(15) 0.0465(12) 0.0644(14) -0.0031(11) 0.0377(13) -0.0203(11) C9 0.0736(14) 0.0384(11) 0.0543(12) -0.0047(9) 0.0320(11) -0.0088(10) C10 0.0502(11) 0.0387(10) 0.0327(9) -0.0005(8) 0.0166(8) -0.0026(8) C11 0.0408(10) 0.0395(10) 0.0463(11) 0.0010(8) 0.0289(9) 0.0015(8) N1 0.0403(8) 0.0419(9) 0.0462(9) -0.0084(7) 0.0235(7) -0.0070(7) N2 0.0550(11) 0.0478(10) 0.0627(11) -0.0066(8) 0.0424(10) -0.0107(8) N3 0.0433(8) 0.0369(8) 0.0346(8) -0.0007(7) 0.0186(7) -0.0040(7) N4 0.0446(10) 0.0623(12) 0.0464(10) 0.0044(9) 0.0189(8) 0.0006(8) S1 0.0383(3) 0.0794(4) 0.0507(3) 0.0033(3) 0.0179(2) 0.0112(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 N3 2.1350(15) 2_655 ? Fe1 N3 2.1350(15) . ? Fe1 N1 2.1457(15) . ? Fe1 N1 2.1457(15) 2_655 ? Fe1 N4 2.1481(18) 2_655 ? Fe1 N4 2.1481(18) . ? C1 N1 1.344(2) . ? C1 C2 1.360(3) . ? C1 H1 0.9300 . ? C2 C3 1.380(3) . ? C2 H2 0.9300 . ? C3 C4 1.357(3) . ? C3 H3 0.9300 . ? C4 C5 1.392(3) . ? C4 H4 0.9300 . ? C5 N1 1.331(2) . ? C5 N2 1.375(3) . ? C6 N3 1.336(2) . ? C6 N2 1.372(3) . ? C6 C7 1.398(3) . ? C7 C8 1.350(3) . ? C7 H7 0.9300 . ? C8 C9 1.380(3) . ? C8 H8 0.9300 . ? C9 C10 1.371(3) . ? C9 H9 0.9300 . ? C10 N3 1.352(2) . ? C10 C10 1.481(4) 2_655 ? C11 N4 1.145(3) . ? C11 S1 1.626(2) . ? N2 H2A 0.841(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Fe1 N3 77.34(8) 2_655 . ? N3 Fe1 N1 158.01(6) 2_655 . ? N3 Fe1 N1 85.74(6) . . ? N3 Fe1 N1 85.74(6) 2_655 2_655 ? N3 Fe1 N1 158.01(6) . 2_655 ? N1 Fe1 N1 113.78(9) . 2_655 ? N3 Fe1 N4 85.26(6) 2_655 2_655 ? N3 Fe1 N4 104.49(6) . 2_655 ? N1 Fe1 N4 85.50(6) . 2_655 ? N1 Fe1 N4 87.78(6) 2_655 2_655 ? N3 Fe1 N4 104.49(6) 2_655 . ? N3 Fe1 N4 85.26(6) . . ? N1 Fe1 N4 87.78(6) . . ? N1 Fe1 N4 85.50(6) 2_655 . ? N4 Fe1 N4 167.67(10) 2_655 . ? N1 C1 C2 124.14(19) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C1 C2 C3 118.0(2) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 119.2(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 119.54(19) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 N2 120.80(17) . . ? N1 C5 C4 121.84(18) . . ? N2 C5 C4 117.36(17) . . ? N3 C6 N2 121.07(16) . . ? N3 C6 C7 122.12(18) . . ? N2 C6 C7 116.80(17) . . ? C8 C7 C6 118.9(2) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C8 C9 119.7(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 119.1(2) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? N3 C10 C9 122.22(18) . . ? N3 C10 C10 115.71(10) . 2_655 ? C9 C10 C10 122.06(13) . 2_655 ? N4 C11 S1 177.53(18) . . ? C5 N1 C1 117.20(17) . . ? C5 N1 Fe1 125.51(13) . . ? C1 N1 Fe1 116.29(13) . . ? C6 N2 C5 133.68(16) . . ? C6 N2 H2A 112.2(16) . . ? C5 N2 H2A 113.0(16) . . ? C6 N3 C10 117.97(16) . . ? C6 N3 Fe1 125.76(13) . . ? C10 N3 Fe1 115.02(12) . . ? C11 N4 Fe1 171.85(16) . . ? 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 C1 C2 C3 0.9(4) . . . . ? C1 C2 C3 C4 1.3(4) . . . . ? C2 C3 C4 C5 -1.5(4) . . . . ? C3 C4 C5 N1 -0.5(3) . . . . ? C3 C4 C5 N2 179.7(2) . . . . ? N3 C6 C7 C8 -0.7(3) . . . . ? N2 C6 C7 C8 178.2(2) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C7 C8 C9 C10 0.3(3) . . . . ? C8 C9 C10 N3 0.6(3) . . . . ? C8 C9 C10 C10 -178.4(2) . . . 2_655 ? N2 C5 N1 C1 -177.64(19) . . . . ? C4 C5 N1 C1 2.5(3) . . . . ? N2 C5 N1 Fe1 14.2(3) . . . . ? C4 C5 N1 Fe1 -165.61(16) . . . . ? C2 C1 N1 C5 -2.8(3) . . . . ? C2 C1 N1 Fe1 166.44(18) . . . . ? N3 Fe1 N1 C5 -65.0(2) 2_655 . . . ? N3 Fe1 N1 C5 -25.48(16) . . . . ? N1 Fe1 N1 C5 144.02(17) 2_655 . . . ? N4 Fe1 N1 C5 -130.41(16) 2_655 . . . ? N4 Fe1 N1 C5 59.93(16) . . . . ? N3 Fe1 N1 C1 126.76(18) 2_655 . . . ? N3 Fe1 N1 C1 166.29(15) . . . . ? N1 Fe1 N1 C1 -24.21(13) 2_655 . . . ? N4 Fe1 N1 C1 61.36(15) 2_655 . . . ? N4 Fe1 N1 C1 -108.30(15) . . . . ? N3 C6 N2 C5 -14.8(3) . . . . ? C7 C6 N2 C5 166.3(2) . . . . ? N1 C5 N2 C6 12.8(3) . . . . ? C4 C5 N2 C6 -167.3(2) . . . . ? N2 C6 N3 C10 -177.32(17) . . . . ? C7 C6 N3 C10 1.5(3) . . . . ? N2 C6 N3 Fe1 -10.8(3) . . . . ? C7 C6 N3 Fe1 168.05(15) . . . . ? C9 C10 N3 C6 -1.5(3) . . . . ? C10 C10 N3 C6 177.54(19) 2_655 . . . ? C9 C10 N3 Fe1 -169.39(16) . . . . ? C10 C10 N3 Fe1 9.6(3) 2_655 . . . ? N3 Fe1 N3 C6 -170.41(18) 2_655 . . . ? N1 Fe1 N3 C6 23.73(15) . . . . ? N1 Fe1 N3 C6 -129.83(17) 2_655 . . . ? N4 Fe1 N3 C6 107.96(15) 2_655 . . . ? N4 Fe1 N3 C6 -64.39(15) . . . . ? N3 Fe1 N3 C10 -3.55(10) 2_655 . . . ? N1 Fe1 N3 C10 -169.41(13) . . . . ? N1 Fe1 N3 C10 37.0(2) 2_655 . . . ? N4 Fe1 N3 C10 -85.19(13) 2_655 . . . ? N4 Fe1 N3 C10 102.47(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A S1 0.841(16) 2.583(16) 3.4237(16) 178(2) 6_566 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.269 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.048 #===END data_phaseII _database_code_depnum_ccdc_archive 'CCDC 694534' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 Fe N8 S2' _chemical_formula_sum 'C22 H16 Fe N8 S2' _chemical_formula_weight 512.40 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 15.7348(2) _cell_length_b 10.7200(2) _cell_length_c 42.3919(5) _cell_angle_alpha 90.00 _cell_angle_beta 116.565(1) _cell_angle_gamma 90.00 _cell_volume 6395.64(16) _cell_formula_units_Z 12 _cell_measurement_temperature 190(1) _cell_measurement_reflns_used 15235 _cell_measurement_theta_min 1.61 _cell_measurement_theta_max 27.49 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3144 _exptl_absorpt_coefficient_mu 0.933 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.663 _exptl_absorpt_correction_T_max 0.846 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35156 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -51 _diffrn_reflns_limit_l_max 51 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5948 _reflns_number_gt 4763 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'PEAKREF (Schreurs, 2005)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0300P)^2^+13.7682P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5948 _refine_ls_number_parameters 456 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 0.50458(2) 0.52939(3) 0.084664(9) 0.01958(11) Uani 1 1 d . . . S1A S 0.20442(5) 0.55181(8) -0.014644(18) 0.03201(18) Uani 1 1 d . . . S2A S 0.80863(5) 0.48550(7) 0.181147(18) 0.03024(18) Uani 1 1 d . . . C1A C 0.49937(19) 0.3118(2) 0.12424(7) 0.0250(6) Uani 1 1 d . . . H1A H 0.5515 0.2883 0.1199 0.030 Uiso 1 1 calc R . . C2A C 0.4699(2) 0.2298(3) 0.14181(7) 0.0293(7) Uani 1 1 d . . . H2A H 0.5001 0.1511 0.1492 0.035 Uiso 1 1 calc R . . C3A C 0.3954(2) 0.2634(3) 0.14874(7) 0.0304(7) Uani 1 1 d . . . H3A H 0.3709 0.2066 0.1599 0.037 Uiso 1 1 calc R . . C4A C 0.3574(2) 0.3795(3) 0.13935(7) 0.0293(6) Uani 1 1 d . . . H4A H 0.3073 0.4056 0.1445 0.035 Uiso 1 1 calc R . . C5A C 0.39273(18) 0.4601(2) 0.12211(6) 0.0227(6) Uani 1 1 d . . . C6A C 0.39584(19) 0.6872(2) 0.10971(6) 0.0238(6) Uani 1 1 d . . . C7A C 0.3595(2) 0.8007(3) 0.11405(7) 0.0290(6) Uani 1 1 d . . . H7A H 0.3111 0.8031 0.1217 0.035 Uiso 1 1 calc R . . C8A C 0.3942(2) 0.9085(3) 0.10723(7) 0.0315(7) Uani 1 1 d . . . H8A H 0.3712 0.9869 0.1105 0.038 Uiso 1 1 calc R . . C9A C 0.4630(2) 0.9030(3) 0.09552(7) 0.0299(7) Uani 1 1 d . . . H9A H 0.4876 0.9773 0.0905 0.036 Uiso 1 1 calc R . . C10A C 0.49532(18) 0.7886(2) 0.09119(6) 0.0244(6) Uani 1 1 d . . . C11A C 0.30704(18) 0.5430(2) 0.02069(6) 0.0207(6) Uani 1 1 d . . . C12A C 0.56024(19) 0.7692(2) 0.07542(6) 0.0244(6) Uani 1 1 d . . . C13A C 0.6121(2) 0.8621(3) 0.07002(7) 0.0325(7) Uani 1 1 d . . . H13A H 0.6054 0.9462 0.0757 0.039 Uiso 1 1 calc R . . C14A C 0.6740(2) 0.8319(3) 0.05629(7) 0.0363(7) Uani 1 1 d . . . H14A H 0.7087 0.8954 0.0515 0.044 Uiso 1 1 calc R . . C15A C 0.6848(2) 0.7102(3) 0.04962(7) 0.0330(7) Uani 1 1 d . . . H15A H 0.7283 0.6878 0.0407 0.040 Uiso 1 1 calc R . . C16A C 0.63148(18) 0.6187(3) 0.05599(6) 0.0250(6) Uani 1 1 d . . . C17A C 0.59628(18) 0.3899(3) 0.04834(7) 0.0253(6) Uani 1 1 d . . . C18A C 0.6158(2) 0.2858(3) 0.03291(7) 0.0315(7) Uani 1 1 d . . . H18A H 0.6673 0.2874 0.0270 0.038 Uiso 1 1 calc R . . C19A C 0.5609(2) 0.1822(3) 0.02647(8) 0.0349(7) Uani 1 1 d . . . H19A H 0.5741 0.1101 0.0164 0.042 Uiso 1 1 calc R . . C20A C 0.4855(2) 0.1836(3) 0.03478(7) 0.0322(7) Uani 1 1 d . . . H20A H 0.4438 0.1142 0.0295 0.039 Uiso 1 1 calc R . . C21A C 0.47224(19) 0.2868(2) 0.05076(7) 0.0268(6) Uani 1 1 d . . . H21A H 0.4199 0.2872 0.0562 0.032 Uiso 1 1 calc R . . C22A C 0.70402(18) 0.5009(2) 0.14712(7) 0.0209(6) Uani 1 1 d . . . N1A N 0.45895(14) 0.42476(19) 0.11247(5) 0.0213(5) Uani 1 1 d . . . N2A N 0.35690(16) 0.5795(2) 0.11532(6) 0.0269(5) Uani 1 1 d D . . H2A1 H 0.3141(16) 0.593(3) 0.1223(7) 0.032 Uiso 1 1 d D . . N3A N 0.46492(15) 0.68067(19) 0.09956(5) 0.0213(5) Uani 1 1 d . . . N4A N 0.38010(15) 0.5370(2) 0.04486(5) 0.0231(5) Uani 1 1 d . . . N5A N 0.56718(15) 0.6478(2) 0.06729(5) 0.0228(5) Uani 1 1 d . . . N6A N 0.64843(16) 0.4962(2) 0.05132(6) 0.0273(5) Uani 1 1 d D . . H6A H 0.6899(17) 0.488(3) 0.0433(7) 0.033 Uiso 1 1 d D . . N7A N 0.52895(15) 0.3890(2) 0.05936(5) 0.0229(5) Uani 1 1 d . . . N8A N 0.62933(15) 0.5134(2) 0.12418(5) 0.0228(5) Uani 1 1 d . . . Fe2 Fe 0.5000 0.55832(5) 0.2500 0.01995(13) Uani 1 2 d S . . S1B S 0.19329(5) 0.61491(7) 0.145539(19) 0.03228(18) Uani 1 1 d . . . C1B C 0.50712(19) 0.7838(3) 0.21008(7) 0.0277(6) Uani 1 1 d . . . H1B H 0.4556 0.8041 0.2151 0.033 Uiso 1 1 calc R . . C2B C 0.5402(2) 0.8738(3) 0.19574(7) 0.0305(7) Uani 1 1 d . . . H2B H 0.5134 0.9552 0.1914 0.037 Uiso 1 1 calc R . . C3B C 0.6135(2) 0.8440(3) 0.18767(7) 0.0313(7) Uani 1 1 d . . . H3B H 0.6387 0.9052 0.1780 0.038 Uiso 1 1 calc R . . C4B C 0.6493(2) 0.7260(3) 0.19371(7) 0.0306(7) Uani 1 1 d . . . H4B H 0.6986 0.7032 0.1877 0.037 Uiso 1 1 calc R . . C5B C 0.61239(18) 0.6386(2) 0.20888(7) 0.0240(6) Uani 1 1 d . . . C6B C 0.62252(18) 0.4082(2) 0.22257(6) 0.0240(6) Uani 1 1 d . . . C7B C 0.6690(2) 0.3014(3) 0.21911(7) 0.0291(6) Uani 1 1 d . . . H7B H 0.7154 0.3076 0.2106 0.035 Uiso 1 1 calc R . . C8B C 0.6465(2) 0.1892(3) 0.22809(7) 0.0323(7) Uani 1 1 d . . . H8B H 0.6770 0.1156 0.2259 0.039 Uiso 1 1 calc R . . C9B C 0.5794(2) 0.1824(3) 0.24043(7) 0.0302(7) Uani 1 1 d . . . H9B H 0.5635 0.1044 0.2470 0.036 Uiso 1 1 calc R . . C10B C 0.53553(18) 0.2899(2) 0.24315(6) 0.0241(6) Uani 1 1 d . . . C11B C 0.28996(19) 0.5956(2) 0.18255(7) 0.0235(6) Uani 1 1 d . . . N1B N 0.54332(15) 0.6676(2) 0.21762(6) 0.0243(5) Uani 1 1 d . . . N2B N 0.64993(16) 0.5202(2) 0.21431(6) 0.0274(5) Uani 1 1 d D . . H2B1 H 0.6927(17) 0.511(3) 0.2070(7) 0.033 Uiso 1 1 d D . . N3B N 0.55618(15) 0.4033(2) 0.23400(5) 0.0217(5) Uani 1 1 d . . . N4B N 0.35864(16) 0.5798(2) 0.20814(6) 0.0299(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 0.0191(2) 0.0217(2) 0.01838(19) 0.00071(15) 0.00877(15) -0.00050(15) S1A 0.0191(3) 0.0522(5) 0.0235(3) -0.0007(3) 0.0084(3) -0.0045(3) S2A 0.0205(4) 0.0386(4) 0.0288(4) 0.0032(3) 0.0084(3) 0.0038(3) C1A 0.0226(14) 0.0260(15) 0.0268(14) 0.0035(12) 0.0113(12) 0.0043(12) C2A 0.0312(16) 0.0248(15) 0.0284(15) 0.0035(12) 0.0104(13) 0.0020(12) C3A 0.0369(17) 0.0276(16) 0.0320(15) 0.0040(12) 0.0201(14) -0.0049(13) C4A 0.0302(15) 0.0310(16) 0.0339(15) -0.0023(13) 0.0209(13) -0.0024(13) C5A 0.0229(14) 0.0233(15) 0.0218(13) -0.0001(11) 0.0098(11) 0.0014(12) C6A 0.0261(15) 0.0236(15) 0.0188(13) 0.0010(11) 0.0076(11) 0.0022(12) C7A 0.0311(16) 0.0277(16) 0.0278(15) -0.0022(12) 0.0128(13) 0.0042(13) C8A 0.0346(16) 0.0243(16) 0.0279(15) -0.0028(12) 0.0069(13) 0.0073(13) C9A 0.0335(16) 0.0251(15) 0.0251(14) 0.0003(12) 0.0077(13) -0.0032(13) C10A 0.0269(15) 0.0206(14) 0.0195(13) -0.0006(11) 0.0048(11) -0.0012(12) C11A 0.0257(15) 0.0211(14) 0.0211(13) 0.0000(11) 0.0156(12) -0.0028(11) C12A 0.0283(15) 0.0227(15) 0.0180(13) 0.0019(11) 0.0064(11) -0.0009(12) C13A 0.0399(17) 0.0235(16) 0.0306(15) 0.0003(12) 0.0126(14) -0.0071(13) C14A 0.0432(18) 0.0330(18) 0.0329(16) 0.0020(13) 0.0172(14) -0.0156(14) C15A 0.0342(16) 0.0372(18) 0.0328(16) -0.0007(13) 0.0197(14) -0.0084(14) C16A 0.0233(14) 0.0320(16) 0.0197(13) 0.0016(11) 0.0097(11) -0.0031(12) C17A 0.0237(14) 0.0292(15) 0.0245(14) 0.0005(12) 0.0120(12) -0.0018(12) C18A 0.0339(16) 0.0330(17) 0.0384(16) -0.0034(13) 0.0258(14) -0.0030(13) C19A 0.0463(19) 0.0273(16) 0.0414(17) -0.0054(13) 0.0287(15) -0.0001(14) C20A 0.0385(17) 0.0258(16) 0.0365(16) -0.0050(13) 0.0204(14) -0.0085(13) C21A 0.0249(14) 0.0275(15) 0.0305(15) -0.0012(12) 0.0146(12) -0.0058(12) C22A 0.0255(15) 0.0187(14) 0.0234(14) 0.0001(10) 0.0153(13) -0.0006(11) N1A 0.0197(11) 0.0224(12) 0.0217(11) 0.0009(9) 0.0091(9) 0.0014(9) N2A 0.0272(13) 0.0279(13) 0.0342(13) 0.0021(10) 0.0213(11) 0.0051(11) N3A 0.0224(11) 0.0206(12) 0.0182(11) 0.0004(9) 0.0067(9) -0.0002(9) N4A 0.0244(12) 0.0247(12) 0.0209(11) 0.0000(9) 0.0109(10) -0.0011(10) N5A 0.0242(12) 0.0236(13) 0.0186(11) 0.0013(9) 0.0077(10) -0.0027(9) N6A 0.0274(13) 0.0304(14) 0.0340(13) -0.0037(10) 0.0226(11) -0.0062(10) N7A 0.0230(12) 0.0241(12) 0.0240(11) -0.0021(10) 0.0127(10) -0.0022(10) N8A 0.0237(12) 0.0234(12) 0.0234(11) 0.0011(9) 0.0125(10) -0.0001(9) Fe2 0.0222(3) 0.0193(3) 0.0214(3) 0.000 0.0125(2) 0.000 S1B 0.0230(4) 0.0418(4) 0.0308(4) -0.0009(3) 0.0108(3) 0.0062(3) C1B 0.0269(15) 0.0274(16) 0.0305(15) 0.0046(12) 0.0142(13) 0.0060(12) C2B 0.0347(16) 0.0234(15) 0.0322(15) 0.0050(12) 0.0138(13) 0.0037(13) C3B 0.0337(16) 0.0285(16) 0.0340(16) 0.0033(13) 0.0171(14) -0.0040(13) C4B 0.0322(16) 0.0327(17) 0.0323(15) -0.0001(13) 0.0193(13) 0.0004(13) C5B 0.0247(15) 0.0264(15) 0.0217(13) -0.0004(11) 0.0112(12) -0.0017(12) C6B 0.0254(14) 0.0259(15) 0.0202(13) 0.0004(11) 0.0098(12) 0.0014(12) C7B 0.0294(15) 0.0307(16) 0.0314(15) -0.0005(12) 0.0174(13) 0.0061(13) C8B 0.0364(17) 0.0276(16) 0.0327(16) 0.0006(13) 0.0152(14) 0.0103(13) C9B 0.0424(17) 0.0202(15) 0.0280(15) 0.0010(12) 0.0158(14) 0.0031(13) C10B 0.0275(14) 0.0236(14) 0.0167(12) 0.0000(11) 0.0059(11) -0.0004(12) C11B 0.0285(15) 0.0203(14) 0.0304(15) -0.0038(11) 0.0210(13) -0.0018(12) N1B 0.0242(12) 0.0227(12) 0.0264(12) 0.0052(9) 0.0118(10) 0.0038(10) N2B 0.0304(13) 0.0269(13) 0.0349(13) 0.0018(10) 0.0234(11) 0.0059(11) N3B 0.0241(12) 0.0240(12) 0.0175(11) -0.0017(9) 0.0097(9) 0.0010(10) N4B 0.0304(14) 0.0335(14) 0.0261(13) 0.0000(10) 0.0129(12) -0.0007(11) _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 N4A 1.932(2) . ? Fe1 N8A 1.936(2) . ? Fe1 N3A 1.942(2) . ? Fe1 N5A 1.942(2) . ? Fe1 N1A 1.980(2) . ? Fe1 N7A 1.983(2) . ? S1A C11A 1.642(3) . ? S2A C22A 1.641(3) . ? C1A N1A 1.355(3) . ? C1A C2A 1.360(4) . ? C1A H1A 0.9500 . ? C2A C3A 1.379(4) . ? C2A H2A 0.9500 . ? C3A C4A 1.361(4) . ? C3A H3A 0.9500 . ? C4A C5A 1.397(4) . ? C4A H4A 0.9500 . ? C5A N1A 1.333(3) . ? C5A N2A 1.377(3) . ? C6A N3A 1.338(3) . ? C6A N2A 1.376(3) . ? C6A C7A 1.392(4) . ? C7A C8A 1.363(4) . ? C7A H7A 0.9500 . ? C8A C9A 1.379(4) . ? C8A H8A 0.9500 . ? C9A C10A 1.371(4) . ? C9A H9A 0.9500 . ? C10A N3A 1.358(3) . ? C10A C12A 1.465(4) . ? C11A N4A 1.150(3) . ? C12A N5A 1.363(3) . ? C12A C13A 1.370(4) . ? C13A C14A 1.378(4) . ? C13A H13A 0.9500 . ? C14A C15A 1.362(4) . ? C14A H14A 0.9500 . ? C15A C16A 1.392(4) . ? C15A H15A 0.9500 . ? C16A N5A 1.336(3) . ? C16A N6A 1.372(4) . ? C17A N7A 1.335(3) . ? C17A N6A 1.376(3) . ? C17A C18A 1.396(4) . ? C18A C19A 1.358(4) . ? C18A H18A 0.9500 . ? C19A C20A 1.381(4) . ? C19A H19A 0.9500 . ? C20A C21A 1.361(4) . ? C20A H20A 0.9500 . ? C21A N7A 1.356(3) . ? C21A H21A 0.9500 . ? C22A N8A 1.150(3) . ? N2A H2A1 0.859(17) . ? N6A H6A 0.864(17) . ? Fe2 N3B 2.130(2) 2_655 ? Fe2 N3B 2.131(2) . ? Fe2 N1B 2.135(2) 2_655 ? Fe2 N1B 2.135(2) . ? Fe2 N4B 2.149(2) . ? Fe2 N4B 2.149(2) 2_655 ? S1B C11B 1.638(3) . ? C1B N1B 1.348(3) . ? C1B C2B 1.361(4) . ? C1B H1B 0.9500 . ? C2B C3B 1.380(4) . ? C2B H2B 0.9500 . ? C3B C4B 1.362(4) . ? C3B H3B 0.9500 . ? C4B C5B 1.401(4) . ? C4B H4B 0.9500 . ? C5B N1B 1.333(3) . ? C5B N2B 1.375(3) . ? C6B N3B 1.334(3) . ? C6B N2B 1.373(3) . ? C6B C7B 1.400(4) . ? C7B C8B 1.356(4) . ? C7B H7B 0.9500 . ? C8B C9B 1.375(4) . ? C8B H8B 0.9500 . ? C9B C10B 1.373(4) . ? C9B H9B 0.9500 . ? C10B N3B 1.359(3) . ? C10B C10B 1.473(5) 2_655 ? C11B N4B 1.151(3) . ? N2B H2B1 0.865(17) . ? 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 N4A Fe1 N8A 177.30(9) . . ? N4A Fe1 N3A 84.32(9) . . ? N8A Fe1 N3A 98.14(9) . . ? N4A Fe1 N5A 97.43(9) . . ? N8A Fe1 N5A 84.04(9) . . ? N3A Fe1 N5A 82.46(9) . . ? N4A Fe1 N1A 92.74(9) . . ? N8A Fe1 N1A 86.10(9) . . ? N3A Fe1 N1A 91.41(9) . . ? N5A Fe1 N1A 167.52(9) . . ? N4A Fe1 N7A 85.72(9) . . ? N8A Fe1 N7A 91.96(9) . . ? N3A Fe1 N7A 167.95(9) . . ? N5A Fe1 N7A 92.13(9) . . ? N1A Fe1 N7A 95.83(9) . . ? N1A C1A C2A 124.1(3) . . ? N1A C1A H1A 118.0 . . ? C2A C1A H1A 118.0 . . ? C1A C2A C3A 118.6(3) . . ? C1A C2A H2A 120.7 . . ? C3A C2A H2A 120.7 . . ? C4A C3A C2A 118.7(3) . . ? C4A C3A H3A 120.7 . . ? C2A C3A H3A 120.7 . . ? C3A C4A C5A 119.6(3) . . ? C3A C4A H4A 120.2 . . ? C5A C4A H4A 120.2 . . ? N1A C5A N2A 120.2(2) . . ? N1A C5A C4A 122.2(2) . . ? N2A C5A C4A 117.6(2) . . ? N3A C6A N2A 120.0(2) . . ? N3A C6A C7A 121.9(3) . . ? N2A C6A C7A 118.0(2) . . ? C8A C7A C6A 119.0(3) . . ? C8A C7A H7A 120.5 . . ? C6A C7A H7A 120.5 . . ? C7A C8A C9A 119.6(3) . . ? C7A C8A H8A 120.2 . . ? C9A C8A H8A 120.2 . . ? C10A C9A C8A 118.9(3) . . ? C10A C9A H9A 120.5 . . ? C8A C9A H9A 120.5 . . ? N3A C10A C9A 122.1(3) . . ? N3A C10A C12A 113.4(2) . . ? C9A C10A C12A 124.3(3) . . ? N4A C11A S1A 178.2(2) . . ? N5A C12A C13A 122.1(3) . . ? N5A C12A C10A 113.7(2) . . ? C13A C12A C10A 124.2(3) . . ? C12A C13A C14A 119.1(3) . . ? C12A C13A H13A 120.5 . . ? C14A C13A H13A 120.5 . . ? C15A C14A C13A 119.3(3) . . ? C15A C14A H14A 120.3 . . ? C13A C14A H14A 120.3 . . ? C14A C15A C16A 119.5(3) . . ? C14A C15A H15A 120.3 . . ? C16A C15A H15A 120.3 . . ? N5A C16A N6A 120.1(2) . . ? N5A C16A C15A 121.6(3) . . ? N6A C16A C15A 118.2(2) . . ? N7A C17A N6A 120.5(2) . . ? N7A C17A C18A 122.2(3) . . ? N6A C17A C18A 117.2(2) . . ? C19A C18A C17A 119.6(3) . . ? C19A C18A H18A 120.2 . . ? C17A C18A H18A 120.2 . . ? C18A C19A C20A 118.8(3) . . ? C18A C19A H19A 120.6 . . ? C20A C19A H19A 120.6 . . ? C21A C20A C19A 118.4(3) . . ? C21A C20A H20A 120.8 . . ? C19A C20A H20A 120.8 . . ? N7A C21A C20A 124.2(3) . . ? N7A C21A H21A 117.9 . . ? C20A C21A H21A 117.9 . . ? N8A C22A S2A 177.3(2) . . ? C5A N1A C1A 116.3(2) . . ? C5A N1A Fe1 124.26(17) . . ? C1A N1A Fe1 119.34(18) . . ? C6A N2A C5A 130.1(2) . . ? C6A N2A H2A1 113(2) . . ? C5A N2A H2A1 113(2) . . ? C6A N3A C10A 118.1(2) . . ? C6A N3A Fe1 125.00(18) . . ? C10A N3A Fe1 115.11(17) . . ? C11A N4A Fe1 178.2(2) . . ? C16A N5A C12A 118.2(2) . . ? C16A N5A Fe1 125.30(18) . . ? C12A N5A Fe1 114.62(18) . . ? C16A N6A C17A 131.2(2) . . ? C16A N6A H6A 112(2) . . ? C17A N6A H6A 114(2) . . ? C17A N7A C21A 116.2(2) . . ? C17A N7A Fe1 124.01(18) . . ? C21A N7A Fe1 119.71(18) . . ? C22A N8A Fe1 177.9(2) . . ? N3B Fe2 N3B 77.47(12) 2_655 . ? N3B Fe2 N1B 85.77(8) 2_655 2_655 ? N3B Fe2 N1B 158.42(8) . 2_655 ? N3B Fe2 N1B 158.41(8) 2_655 . ? N3B Fe2 N1B 85.76(8) . . ? N1B Fe2 N1B 113.44(12) 2_655 . ? N3B Fe2 N4B 85.58(8) 2_655 . ? N3B Fe2 N4B 104.13(8) . . ? N1B Fe2 N4B 87.82(8) 2_655 . ? N1B Fe2 N4B 85.44(8) . . ? N3B Fe2 N4B 104.13(8) 2_655 2_655 ? N3B Fe2 N4B 85.58(8) . 2_655 ? N1B Fe2 N4B 85.44(8) 2_655 2_655 ? N1B Fe2 N4B 87.83(8) . 2_655 ? N4B Fe2 N4B 167.70(13) . 2_655 ? N1B C1B C2B 123.8(3) . . ? N1B C1B H1B 118.1 . . ? C2B C1B H1B 118.1 . . ? C1B C2B C3B 118.4(3) . . ? C1B C2B H2B 120.8 . . ? C3B C2B H2B 120.8 . . ? C4B C3B C2B 119.4(3) . . ? C4B C3B H3B 120.3 . . ? C2B C3B H3B 120.3 . . ? C3B C4B C5B 119.1(3) . . ? C3B C4B H4B 120.5 . . ? C5B C4B H4B 120.5 . . ? N1B C5B N2B 120.8(2) . . ? N1B C5B C4B 121.9(2) . . ? N2B C5B C4B 117.3(2) . . ? N3B C6B N2B 120.8(2) . . ? N3B C6B C7B 122.4(3) . . ? N2B C6B C7B 116.7(2) . . ? C8B C7B C6B 118.8(3) . . ? C8B C7B H7B 120.6 . . ? C6B C7B H7B 120.6 . . ? C7B C8B C9B 119.7(3) . . ? C7B C8B H8B 120.2 . . ? C9B C8B H8B 120.2 . . ? C10B C9B C8B 119.2(3) . . ? C10B C9B H9B 120.4 . . ? C8B C9B H9B 120.4 . . ? N3B C10B C9B 122.2(3) . . ? N3B C10B C10B 115.66(15) . 2_655 ? C9B C10B C10B 122.11(17) . 2_655 ? N4B C11B S1B 178.2(3) . . ? C5B N1B C1B 117.4(2) . . ? C5B N1B Fe2 125.83(17) . . ? C1B N1B Fe2 115.93(18) . . ? C6B N2B C5B 133.6(2) . . ? C6B N2B H2B1 112(2) . . ? C5B N2B H2B1 113(2) . . ? C6B N3B C10B 117.7(2) . . ? C6B N3B Fe2 126.06(18) . . ? C10B N3B Fe2 114.90(17) . . ? C11B N4B Fe2 169.3(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 N1A C1A C2A C3A -1.1(4) . . . . ? C1A C2A C3A C4A -3.3(4) . . . . ? C2A C3A C4A C5A 1.9(4) . . . . ? C3A C4A C5A N1A 4.2(4) . . . . ? C3A C4A C5A N2A -175.5(2) . . . . ? N3A C6A C7A C8A 1.0(4) . . . . ? N2A C6A C7A C8A -177.3(2) . . . . ? C6A C7A C8A C9A 1.3(4) . . . . ? C7A C8A C9A C10A -0.4(4) . . . . ? C8A C9A C10A N3A -3.0(4) . . . . ? C8A C9A C10A C12A 173.1(2) . . . . ? N3A C10A C12A N5A 9.1(3) . . . . ? C9A C10A C12A N5A -167.3(2) . . . . ? N3A C10A C12A C13A -169.0(2) . . . . ? C9A C10A C12A C13A 14.5(4) . . . . ? N5A C12A C13A C14A -0.7(4) . . . . ? C10A C12A C13A C14A 177.3(2) . . . . ? C12A C13A C14A C15A -2.4(4) . . . . ? C13A C14A C15A C16A 1.5(4) . . . . ? C14A C15A C16A N5A 2.5(4) . . . . ? C14A C15A C16A N6A -175.7(3) . . . . ? N7A C17A C18A C19A 4.7(4) . . . . ? N6A C17A C18A C19A -174.2(3) . . . . ? C17A C18A C19A C20A 1.3(4) . . . . ? C18A C19A C20A C21A -3.3(4) . . . . ? C19A C20A C21A N7A -0.4(4) . . . . ? N2A C5A N1A C1A 171.5(2) . . . . ? C4A C5A N1A C1A -8.3(4) . . . . ? N2A C5A N1A Fe1 -5.4(3) . . . . ? C4A C5A N1A Fe1 174.88(19) . . . . ? C2A C1A N1A C5A 6.8(4) . . . . ? C2A C1A N1A Fe1 -176.2(2) . . . . ? N4A Fe1 N1A C5A -61.2(2) . . . . ? N8A Fe1 N1A C5A 121.2(2) . . . . ? N3A Fe1 N1A C5A 23.1(2) . . . . ? N5A Fe1 N1A C5A 83.4(5) . . . . ? N7A Fe1 N1A C5A -147.2(2) . . . . ? N4A Fe1 N1A C1A 121.99(19) . . . . ? N8A Fe1 N1A C1A -55.57(19) . . . . ? N3A Fe1 N1A C1A -153.63(19) . . . . ? N5A Fe1 N1A C1A -93.4(4) . . . . ? N7A Fe1 N1A C1A 36.01(19) . . . . ? N3A C6A N2A C5A 20.9(4) . . . . ? C7A C6A N2A C5A -160.7(3) . . . . ? N1A C5A N2A C6A -23.1(4) . . . . ? C4A C5A N2A C6A 156.6(3) . . . . ? N2A C6A N3A C10A 174.1(2) . . . . ? C7A C6A N3A C10A -4.3(4) . . . . ? N2A C6A N3A Fe1 10.0(3) . . . . ? C7A C6A N3A Fe1 -168.37(19) . . . . ? C9A C10A N3A C6A 5.3(4) . . . . ? C12A C10A N3A C6A -171.2(2) . . . . ? C9A C10A N3A Fe1 170.9(2) . . . . ? C12A C10A N3A Fe1 -5.6(3) . . . . ? N4A Fe1 N3A C6A 67.1(2) . . . . ? N8A Fe1 N3A C6A -111.7(2) . . . . ? N5A Fe1 N3A C6A 165.4(2) . . . . ? N1A Fe1 N3A C6A -25.5(2) . . . . ? N7A Fe1 N3A C6A 101.5(4) . . . . ? N4A Fe1 N3A C10A -97.39(18) . . . . ? N8A Fe1 N3A C10A 83.74(18) . . . . ? N5A Fe1 N3A C10A 0.91(17) . . . . ? N1A Fe1 N3A C10A 170.00(18) . . . . ? N7A Fe1 N3A C10A -63.0(5) . . . . ? N6A C16A N5A C12A 172.6(2) . . . . ? C15A C16A N5A C12A -5.5(4) . . . . ? N6A C16A N5A Fe1 9.2(3) . . . . ? C15A C16A N5A Fe1 -168.90(19) . . . . ? C13A C12A N5A C16A 4.6(4) . . . . ? C10A C12A N5A C16A -173.6(2) . . . . ? C13A C12A N5A Fe1 169.8(2) . . . . ? C10A C12A N5A Fe1 -8.4(3) . . . . ? N4A Fe1 N5A C16A -108.5(2) . . . . ? N8A Fe1 N5A C16A 69.2(2) . . . . ? N3A Fe1 N5A C16A 168.3(2) . . . . ? N1A Fe1 N5A C16A 107.2(4) . . . . ? N7A Fe1 N5A C16A -22.5(2) . . . . ? N4A Fe1 N5A C12A 87.58(18) . . . . ? N8A Fe1 N5A C12A -94.70(18) . . . . ? N3A Fe1 N5A C12A 4.35(17) . . . . ? N1A Fe1 N5A C12A -56.8(5) . . . . ? N7A Fe1 N5A C12A 173.54(18) . . . . ? N5A C16A N6A C17A 17.2(4) . . . . ? C15A C16A N6A C17A -164.7(3) . . . . ? N7A C17A N6A C16A -18.7(4) . . . . ? C18A C17A N6A C16A 160.2(3) . . . . ? N6A C17A N7A C21A 170.8(2) . . . . ? C18A C17A N7A C21A -8.1(4) . . . . ? N6A C17A N7A Fe1 -6.0(3) . . . . ? C18A C17A N7A Fe1 175.2(2) . . . . ? C20A C21A N7A C17A 6.0(4) . . . . ? C20A C21A N7A Fe1 -177.1(2) . . . . ? N4A Fe1 N7A C17A 118.1(2) . . . . ? N8A Fe1 N7A C17A -63.3(2) . . . . ? N3A Fe1 N7A C17A 83.7(5) . . . . ? N5A Fe1 N7A C17A 20.8(2) . . . . ? N1A Fe1 N7A C17A -149.6(2) . . . . ? N4A Fe1 N7A C21A -58.6(2) . . . . ? N8A Fe1 N7A C21A 120.0(2) . . . . ? N3A Fe1 N7A C21A -92.9(5) . . . . ? N5A Fe1 N7A C21A -155.8(2) . . . . ? N1A Fe1 N7A C21A 33.8(2) . . . . ? N1B C1B C2B C3B 1.5(4) . . . . ? C1B C2B C3B C4B 1.0(4) . . . . ? C2B C3B C4B C5B -1.7(4) . . . . ? C3B C4B C5B N1B -0.1(4) . . . . ? C3B C4B C5B N2B 179.5(3) . . . . ? N3B C6B C7B C8B -0.8(4) . . . . ? N2B C6B C7B C8B 177.8(3) . . . . ? C6B C7B C8B C9B -0.2(4) . . . . ? C7B C8B C9B C10B 0.6(4) . . . . ? C8B C9B C10B N3B 0.1(4) . . . . ? C8B C9B C10B C10B -178.7(3) . . . 2_655 ? N2B C5B N1B C1B -177.1(2) . . . . ? C4B C5B N1B C1B 2.5(4) . . . . ? N2B C5B N1B Fe2 13.7(3) . . . . ? C4B C5B N1B Fe2 -166.69(19) . . . . ? C2B C1B N1B C5B -3.3(4) . . . . ? C2B C1B N1B Fe2 167.0(2) . . . . ? N3B Fe2 N1B C5B -63.8(3) 2_655 . . . ? N3B Fe2 N1B C5B -24.9(2) . . . . ? N1B Fe2 N1B C5B 144.9(2) 2_655 . . . ? N4B Fe2 N1B C5B -129.4(2) . . . . ? N4B Fe2 N1B C5B 60.8(2) 2_655 . . . ? N3B Fe2 N1B C1B 126.9(2) 2_655 . . . ? N3B Fe2 N1B C1B 165.78(19) . . . . ? N1B Fe2 N1B C1B -24.42(16) 2_655 . . . ? N4B Fe2 N1B C1B 61.21(19) . . . . ? N4B Fe2 N1B C1B -108.49(19) 2_655 . . . ? N3B C6B N2B C5B -13.8(4) . . . . ? C7B C6B N2B C5B 167.6(3) . . . . ? N1B C5B N2B C6B 12.5(4) . . . . ? C4B C5B N2B C6B -167.1(3) . . . . ? N2B C6B N3B C10B -177.2(2) . . . . ? C7B C6B N3B C10B 1.3(4) . . . . ? N2B C6B N3B Fe2 -11.3(3) . . . . ? C7B C6B N3B Fe2 167.18(19) . . . . ? C9B C10B N3B C6B -1.0(4) . . . . ? C10B C10B N3B C6B 177.8(3) 2_655 . . . ? C9B C10B N3B Fe2 -168.4(2) . . . . ? C10B C10B N3B Fe2 10.4(3) 2_655 . . . ? N3B Fe2 N3B C6B -170.0(2) 2_655 . . . ? N1B Fe2 N3B C6B -130.1(2) 2_655 . . . ? N1B Fe2 N3B C6B 23.7(2) . . . . ? N4B Fe2 N3B C6B 107.9(2) . . . . ? N4B Fe2 N3B C6B -64.4(2) 2_655 . . . ? N3B Fe2 N3B C10B -3.82(13) 2_655 . . . ? N1B Fe2 N3B C10B 36.1(3) 2_655 . . . ? N1B Fe2 N3B C10B -170.13(18) . . . . ? N4B Fe2 N3B C10B -85.93(18) . . . . ? N4B Fe2 N3B C10B 101.73(18) 2_655 . . . ? N3B Fe2 N4B C11B -140.6(12) 2_655 . . . ? N3B Fe2 N4B C11B -64.7(12) . . . . ? N1B Fe2 N4B C11B 133.5(12) 2_655 . . . ? N1B Fe2 N4B C11B 19.7(12) . . . . ? N4B Fe2 N4B C11B 76.7(12) 2_655 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2A H2A1 S1B 0.859(17) 2.514(18) 3.371(2) 175(3) . N6A H6A S1A 0.864(17) 2.497(18) 3.356(2) 173(3) 5_665 N2B H2B1 S2A 0.865(17) 2.527(18) 3.390(2) 176(3) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.687 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.064 #===END data_phaseIII _database_code_depnum_ccdc_archive 'CCDC 694535' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 Fe N8 S2' _chemical_formula_sum 'C22 H16 Fe N8 S2' _chemical_formula_weight 512.40 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 triclinic _symmetry_space_group_name_H-M 'C -1' _symmetry_space_group_name_Hall '-C 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, y+1/2, z' '-x, -y, -z' '-x+1/2, -y+1/2, -z' _cell_length_a 15.7337(7) _cell_length_b 10.5731(6) _cell_length_c 14.1664(6) _cell_angle_alpha 93.971(4) _cell_angle_beta 116.104(3) _cell_angle_gamma 90.375(5) _cell_volume 2109.37(18) _cell_formula_units_Z 4 _cell_measurement_temperature 110(1) _cell_measurement_reflns_used 10251 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.50 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.943 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.762 _exptl_absorpt_correction_T_max 0.840 _exptl_absorpt_process_details '(TWINABS; Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4842 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0129 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4842 _reflns_number_gt 4361 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'PEAKREF (Schreurs, 2005)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0177P)^2^+5.4558P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4842 _refine_ls_number_parameters 305 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.205 _refine_ls_restrained_S_all 1.205 _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 0.50295(3) 0.49472(4) 0.25570(3) 0.01151(9) Uani 1 1 d . . . S1 S 0.20569(4) 0.44646(7) -0.04471(5) 0.01987(15) Uani 1 1 d . . . S2 S 0.80259(4) 0.57179(7) 0.55121(5) 0.01746(14) Uani 1 1 d . . . C1 C 0.49708(18) 0.7295(2) 0.3709(2) 0.0153(5) Uani 1 1 d . . . H1 H 0.5494 0.7514 0.3578 0.018 Uiso 1 1 calc R . . C2 C 0.46729(19) 0.8188(3) 0.4222(2) 0.0178(5) Uani 1 1 d . . . H2 H 0.4978 0.9007 0.4436 0.021 Uiso 1 1 calc R . . C3 C 0.39132(19) 0.7880(3) 0.4428(2) 0.0185(5) Uani 1 1 d . . . H3 H 0.3665 0.8499 0.4748 0.022 Uiso 1 1 calc R . . C4 C 0.35301(19) 0.6667(3) 0.4161(2) 0.0182(5) Uani 1 1 d . . . H4 H 0.3024 0.6423 0.4313 0.022 Uiso 1 1 calc R . . C5 C 0.38941(17) 0.5786(2) 0.36586(19) 0.0142(5) Uani 1 1 d . . . C6 C 0.39066(18) 0.3447(2) 0.32958(19) 0.0145(5) Uani 1 1 d . . . C7 C 0.35187(19) 0.2302(3) 0.3409(2) 0.0178(5) Uani 1 1 d . . . H7 H 0.3026 0.2307 0.3624 0.021 Uiso 1 1 calc R . . C8 C 0.3857(2) 0.1179(3) 0.3208(2) 0.0196(6) Uani 1 1 d . . . H8 H 0.3610 0.0398 0.3298 0.024 Uiso 1 1 calc R . . C9 C 0.45604(19) 0.1186(3) 0.2869(2) 0.0175(5) Uani 1 1 d . . . H9 H 0.4800 0.0414 0.2720 0.021 Uiso 1 1 calc R . . C10 C 0.49051(18) 0.2344(2) 0.27551(19) 0.0145(5) Uani 1 1 d . . . C11 C 0.30718(17) 0.4638(2) 0.06275(19) 0.0136(5) Uani 1 1 d . . . C12 C 0.55697(19) 0.2482(2) 0.22951(19) 0.0158(5) Uani 1 1 d . . . C13 C 0.60791(19) 0.1504(3) 0.2132(2) 0.0195(5) Uani 1 1 d . . . H13 H 0.6000 0.0670 0.2298 0.023 Uiso 1 1 calc R . . C14 C 0.6709(2) 0.1763(3) 0.1719(2) 0.0217(6) Uani 1 1 d . . . H14 H 0.7053 0.1100 0.1581 0.026 Uiso 1 1 calc R . . C15 C 0.68308(19) 0.2982(3) 0.1511(2) 0.0203(6) Uani 1 1 d . . . H15 H 0.7267 0.3174 0.1240 0.024 Uiso 1 1 calc R . . C16 C 0.63012(18) 0.3940(3) 0.17058(19) 0.0154(5) Uani 1 1 d . . . C17 C 0.59603(18) 0.6233(3) 0.1455(2) 0.0157(5) Uani 1 1 d . . . C18 C 0.6165(2) 0.7232(3) 0.0976(2) 0.0206(6) Uani 1 1 d . . . H18 H 0.6683 0.7195 0.0802 0.025 Uiso 1 1 calc R . . C19 C 0.5608(2) 0.8262(3) 0.0764(2) 0.0216(6) Uani 1 1 d . . . H19 H 0.5739 0.8956 0.0451 0.026 Uiso 1 1 calc R . . C20 C 0.4848(2) 0.8279(3) 0.1013(2) 0.0193(5) Uani 1 1 d . . . H20 H 0.4430 0.8962 0.0843 0.023 Uiso 1 1 calc R . . C21 C 0.47164(18) 0.7286(3) 0.1511(2) 0.0161(5) Uani 1 1 d . . . H21 H 0.4191 0.7298 0.1672 0.019 Uiso 1 1 calc R . . C22 C 0.69994(18) 0.5446(2) 0.4466(2) 0.0138(5) Uani 1 1 d . . . N1 N 0.45653(15) 0.6106(2) 0.33708(16) 0.0133(4) Uani 1 1 d . . . N2 N 0.35258(16) 0.4558(2) 0.34611(18) 0.0170(4) Uani 1 1 d D . . H2A H 0.3058(17) 0.442(3) 0.361(2) 0.020 Uiso 1 1 d D . . N3 N 0.46122(15) 0.3469(2) 0.30065(16) 0.0133(4) Uani 1 1 d . . . N4 N 0.37965(15) 0.4748(2) 0.13590(16) 0.0137(4) Uani 1 1 d . . . N5 N 0.56554(15) 0.3685(2) 0.20487(16) 0.0139(4) Uani 1 1 d . . . N6 N 0.64837(16) 0.5169(2) 0.15607(18) 0.0176(5) Uani 1 1 d D . . H6A H 0.6919(18) 0.521(3) 0.134(2) 0.021 Uiso 1 1 d D . . N7 N 0.52838(15) 0.6288(2) 0.17875(16) 0.0146(4) Uani 1 1 d . . . N8 N 0.62673(15) 0.5231(2) 0.37521(17) 0.0151(4) 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 0.01122(16) 0.01266(17) 0.01096(17) 0.00031(13) 0.00526(13) 0.00052(13) S1 0.0110(3) 0.0342(4) 0.0137(3) 0.0015(3) 0.0048(2) 0.0030(3) S2 0.0115(3) 0.0226(3) 0.0164(3) 0.0002(3) 0.0046(2) -0.0023(3) C1 0.0143(12) 0.0149(12) 0.0157(12) 0.0011(10) 0.0056(10) -0.0003(10) C2 0.0198(13) 0.0161(12) 0.0156(12) 0.0015(10) 0.0060(10) -0.0003(10) C3 0.0199(13) 0.0194(13) 0.0166(12) 0.0000(10) 0.0086(11) 0.0040(10) C4 0.0182(13) 0.0217(13) 0.0177(12) 0.0025(11) 0.0104(11) 0.0008(11) C5 0.0127(11) 0.0154(12) 0.0129(11) 0.0010(10) 0.0044(9) 0.0012(10) C6 0.0144(12) 0.0169(13) 0.0110(11) 0.0027(9) 0.0043(10) -0.0010(10) C7 0.0170(12) 0.0200(13) 0.0156(12) 0.0031(10) 0.0065(10) -0.0029(10) C8 0.0217(13) 0.0174(13) 0.0156(12) 0.0039(10) 0.0042(11) -0.0031(10) C9 0.0197(13) 0.0158(13) 0.0132(12) 0.0009(10) 0.0039(10) 0.0006(10) C10 0.0156(12) 0.0138(12) 0.0106(11) 0.0007(9) 0.0027(9) 0.0019(10) C11 0.0159(12) 0.0135(12) 0.0148(11) 0.0017(9) 0.0097(10) 0.0020(10) C12 0.0175(12) 0.0169(13) 0.0095(11) -0.0003(9) 0.0031(10) 0.0010(10) C13 0.0235(14) 0.0158(13) 0.0161(12) 0.0005(10) 0.0060(11) 0.0048(11) C14 0.0237(14) 0.0228(14) 0.0179(13) -0.0003(11) 0.0087(11) 0.0089(11) C15 0.0188(13) 0.0260(14) 0.0187(13) 0.0025(11) 0.0105(11) 0.0073(11) C16 0.0146(12) 0.0179(12) 0.0120(11) 0.0022(10) 0.0041(10) 0.0042(10) C17 0.0147(12) 0.0176(12) 0.0143(12) 0.0006(10) 0.0058(10) 0.0005(10) C18 0.0219(14) 0.0209(13) 0.0240(14) 0.0021(11) 0.0147(12) 0.0011(11) C19 0.0285(15) 0.0184(14) 0.0221(14) 0.0041(11) 0.0148(12) 0.0004(11) C20 0.0223(13) 0.0169(13) 0.0203(13) 0.0035(10) 0.0104(11) 0.0052(10) C21 0.0155(12) 0.0170(12) 0.0172(12) 0.0017(10) 0.0084(10) 0.0030(10) C22 0.0180(12) 0.0108(12) 0.0173(12) 0.0017(9) 0.0120(11) 0.0013(9) N1 0.0131(10) 0.0139(10) 0.0124(10) 0.0000(8) 0.0053(8) -0.0001(8) N2 0.0166(10) 0.0172(11) 0.0219(11) 0.0003(9) 0.0132(9) -0.0029(9) N3 0.0135(10) 0.0157(11) 0.0099(9) 0.0012(8) 0.0044(8) 0.0000(8) N4 0.0165(10) 0.0122(10) 0.0137(10) 0.0010(8) 0.0079(9) 0.0008(8) N5 0.0136(10) 0.0149(10) 0.0118(10) 0.0003(8) 0.0044(8) 0.0016(8) N6 0.0171(10) 0.0208(12) 0.0210(11) 0.0037(9) 0.0136(9) 0.0042(9) N7 0.0142(10) 0.0173(11) 0.0129(10) 0.0006(8) 0.0067(8) -0.0017(9) N8 0.0174(11) 0.0142(10) 0.0156(10) -0.0001(8) 0.0093(9) 0.0006(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 N4 1.933(2) . ? Fe1 N8 1.942(2) . ? Fe1 N3 1.942(2) . ? Fe1 N5 1.943(2) . ? Fe1 N1 1.980(2) . ? Fe1 N7 1.987(2) . ? S1 C11 1.649(3) . ? S2 C22 1.648(3) . ? C1 C2 1.361(4) . ? C1 N1 1.361(3) . ? C1 H1 0.9500 . ? C2 C3 1.391(4) . ? C2 H2 0.9500 . ? C3 C4 1.369(4) . ? C3 H3 0.9500 . ? C4 C5 1.406(4) . ? C4 H4 0.9500 . ? C5 N1 1.337(3) . ? C5 N2 1.378(3) . ? C6 N3 1.343(3) . ? C6 N2 1.374(3) . ? C6 C7 1.402(4) . ? C7 C8 1.368(4) . ? C7 H7 0.9500 . ? C8 C9 1.387(4) . ? C8 H8 0.9500 . ? C9 C10 1.385(4) . ? C9 H9 0.9500 . ? C10 N3 1.359(3) . ? C10 C12 1.466(4) . ? C11 N4 1.153(3) . ? C12 N5 1.364(3) . ? C12 C13 1.380(4) . ? C13 C14 1.388(4) . ? C13 H13 0.9500 . ? C14 C15 1.372(4) . ? C14 H14 0.9500 . ? C15 C16 1.404(4) . ? C15 H15 0.9500 . ? C16 N5 1.338(3) . ? C16 N6 1.378(4) . ? C17 N7 1.341(3) . ? C17 N6 1.375(3) . ? C17 C18 1.403(4) . ? C18 C19 1.368(4) . ? C18 H18 0.9500 . ? C19 C20 1.387(4) . ? C19 H19 0.9500 . ? C20 C21 1.368(4) . ? C20 H20 0.9500 . ? C21 N7 1.351(3) . ? C21 H21 0.9500 . ? C22 N8 1.158(3) . ? N2 H2A 0.861(18) . ? N6 H6A 0.872(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Fe1 N8 177.34(10) . . ? N4 Fe1 N3 84.18(9) . . ? N8 Fe1 N3 98.16(9) . . ? N4 Fe1 N5 97.18(9) . . ? N8 Fe1 N5 84.41(9) . . ? N3 Fe1 N5 82.67(9) . . ? N4 Fe1 N1 92.75(9) . . ? N8 Fe1 N1 85.94(9) . . ? N3 Fe1 N1 91.41(9) . . ? N5 Fe1 N1 167.84(9) . . ? N4 Fe1 N7 85.34(9) . . ? N8 Fe1 N7 92.48(9) . . ? N3 Fe1 N7 167.66(9) . . ? N5 Fe1 N7 92.22(9) . . ? N1 Fe1 N7 95.58(9) . . ? C2 C1 N1 124.0(2) . . ? C2 C1 H1 118.0 . . ? N1 C1 H1 118.0 . . ? C1 C2 C3 118.8(3) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 118.6(3) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 119.2(2) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 N2 120.3(2) . . ? N1 C5 C4 122.5(2) . . ? N2 C5 C4 117.2(2) . . ? N3 C6 N2 120.3(2) . . ? N3 C6 C7 121.6(2) . . ? N2 C6 C7 118.1(2) . . ? C8 C7 C6 119.4(2) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 119.6(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 118.4(2) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? N3 C10 C9 122.6(2) . . ? N3 C10 C12 113.5(2) . . ? C9 C10 C12 123.8(2) . . ? N4 C11 S1 177.7(2) . . ? N5 C12 C13 122.1(2) . . ? N5 C12 C10 113.7(2) . . ? C13 C12 C10 124.2(2) . . ? C12 C13 C14 118.8(3) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 119.6(3) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 119.0(3) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? N5 C16 N6 120.4(2) . . ? N5 C16 C15 121.6(3) . . ? N6 C16 C15 117.9(2) . . ? N7 C17 N6 120.8(2) . . ? N7 C17 C18 122.5(2) . . ? N6 C17 C18 116.7(2) . . ? C19 C18 C17 119.0(3) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C18 C19 C20 119.1(3) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? C21 C20 C19 118.2(3) . . ? C21 C20 H20 120.9 . . ? C19 C20 H20 120.9 . . ? N7 C21 C20 124.4(2) . . ? N7 C21 H21 117.8 . . ? C20 C21 H21 117.8 . . ? N8 C22 S2 177.5(2) . . ? C5 N1 C1 116.4(2) . . ? C5 N1 Fe1 124.32(17) . . ? C1 N1 Fe1 119.21(18) . . ? C6 N2 C5 129.9(2) . . ? C6 N2 H2A 112(2) . . ? C5 N2 H2A 117(2) . . ? C6 N3 C10 118.2(2) . . ? C6 N3 Fe1 124.85(18) . . ? C10 N3 Fe1 114.89(17) . . ? C11 N4 Fe1 178.2(2) . . ? C16 N5 C12 118.7(2) . . ? C16 N5 Fe1 125.21(18) . . ? C12 N5 Fe1 114.42(17) . . ? C17 N6 C16 130.7(2) . . ? C17 N6 H6A 116(2) . . ? C16 N6 H6A 112(2) . . ? C17 N7 C21 116.3(2) . . ? C17 N7 Fe1 123.81(19) . . ? C21 N7 Fe1 119.71(17) . . ? C22 N8 Fe1 177.6(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 C1 C2 C3 0.6(4) . . . . ? C1 C2 C3 C4 3.7(4) . . . . ? C2 C3 C4 C5 -2.0(4) . . . . ? C3 C4 C5 N1 -4.2(4) . . . . ? C3 C4 C5 N2 176.2(2) . . . . ? N3 C6 C7 C8 -0.9(4) . . . . ? N2 C6 C7 C8 177.3(2) . . . . ? C6 C7 C8 C9 -1.6(4) . . . . ? C7 C8 C9 C10 0.5(4) . . . . ? C8 C9 C10 N3 3.1(4) . . . . ? C8 C9 C10 C12 -173.0(2) . . . . ? N3 C10 C12 N5 -9.9(3) . . . . ? C9 C10 C12 N5 166.5(2) . . . . ? N3 C10 C12 C13 169.3(2) . . . . ? C9 C10 C12 C13 -14.3(4) . . . . ? N5 C12 C13 C14 1.0(4) . . . . ? C10 C12 C13 C14 -178.1(2) . . . . ? C12 C13 C14 C15 1.8(4) . . . . ? C13 C14 C15 C16 -1.0(4) . . . . ? C14 C15 C16 N5 -2.7(4) . . . . ? C14 C15 C16 N6 175.6(2) . . . . ? N7 C17 C18 C19 -5.3(4) . . . . ? N6 C17 C18 C19 174.1(3) . . . . ? C17 C18 C19 C20 -1.0(4) . . . . ? C18 C19 C20 C21 3.2(4) . . . . ? C19 C20 C21 N7 0.7(4) . . . . ? N2 C5 N1 C1 -172.2(2) . . . . ? C4 C5 N1 C1 8.2(4) . . . . ? N2 C5 N1 Fe1 4.9(3) . . . . ? C4 C5 N1 Fe1 -174.67(19) . . . . ? C2 C1 N1 C5 -6.5(4) . . . . ? C2 C1 N1 Fe1 176.3(2) . . . . ? N4 Fe1 N1 C5 61.5(2) . . . . ? N8 Fe1 N1 C5 -120.8(2) . . . . ? N3 Fe1 N1 C5 -22.7(2) . . . . ? N5 Fe1 N1 C5 -83.3(5) . . . . ? N7 Fe1 N1 C5 147.1(2) . . . . ? N4 Fe1 N1 C1 -121.46(19) . . . . ? N8 Fe1 N1 C1 56.22(19) . . . . ? N3 Fe1 N1 C1 154.31(19) . . . . ? N5 Fe1 N1 C1 93.8(5) . . . . ? N7 Fe1 N1 C1 -35.88(19) . . . . ? N3 C6 N2 C5 -19.6(4) . . . . ? C7 C6 N2 C5 162.1(3) . . . . ? N1 C5 N2 C6 22.7(4) . . . . ? C4 C5 N2 C6 -157.7(3) . . . . ? N2 C6 N3 C10 -173.9(2) . . . . ? C7 C6 N3 C10 4.3(4) . . . . ? N2 C6 N3 Fe1 -11.0(3) . . . . ? C7 C6 N3 Fe1 167.15(19) . . . . ? C9 C10 N3 C6 -5.5(4) . . . . ? C12 C10 N3 C6 171.0(2) . . . . ? C9 C10 N3 Fe1 -170.0(2) . . . . ? C12 C10 N3 Fe1 6.5(3) . . . . ? N4 Fe1 N3 C6 -66.8(2) . . . . ? N8 Fe1 N3 C6 111.9(2) . . . . ? N5 Fe1 N3 C6 -164.8(2) . . . . ? N1 Fe1 N3 C6 25.8(2) . . . . ? N7 Fe1 N3 C6 -98.7(5) . . . . ? N4 Fe1 N3 C10 96.55(18) . . . . ? N8 Fe1 N3 C10 -84.72(18) . . . . ? N5 Fe1 N3 C10 -1.49(17) . . . . ? N1 Fe1 N3 C10 -170.83(18) . . . . ? N7 Fe1 N3 C10 64.6(5) . . . . ? N6 C16 N5 C12 -172.8(2) . . . . ? C15 C16 N5 C12 5.4(4) . . . . ? N6 C16 N5 Fe1 -8.6(3) . . . . ? C15 C16 N5 Fe1 169.62(19) . . . . ? C13 C12 N5 C16 -4.7(4) . . . . ? C10 C12 N5 C16 174.5(2) . . . . ? C13 C12 N5 Fe1 -170.5(2) . . . . ? C10 C12 N5 Fe1 8.7(3) . . . . ? N4 Fe1 N5 C16 107.9(2) . . . . ? N8 Fe1 N5 C16 -70.0(2) . . . . ? N3 Fe1 N5 C16 -169.0(2) . . . . ? N1 Fe1 N5 C16 -107.6(5) . . . . ? N7 Fe1 N5 C16 22.3(2) . . . . ? N4 Fe1 N5 C12 -87.35(18) . . . . ? N8 Fe1 N5 C12 94.81(18) . . . . ? N3 Fe1 N5 C12 -4.20(18) . . . . ? N1 Fe1 N5 C12 57.2(5) . . . . ? N7 Fe1 N5 C12 -172.92(18) . . . . ? N7 C17 N6 C16 20.0(4) . . . . ? C18 C17 N6 C16 -159.4(3) . . . . ? N5 C16 N6 C17 -18.3(4) . . . . ? C15 C16 N6 C17 163.4(3) . . . . ? N6 C17 N7 C21 -170.5(2) . . . . ? C18 C17 N7 C21 8.8(4) . . . . ? N6 C17 N7 Fe1 5.1(3) . . . . ? C18 C17 N7 Fe1 -175.61(19) . . . . ? C20 C21 N7 C17 -6.6(4) . . . . ? C20 C21 N7 Fe1 177.7(2) . . . . ? N4 Fe1 N7 C17 -117.5(2) . . . . ? N8 Fe1 N7 C17 64.0(2) . . . . ? N3 Fe1 N7 C17 -85.6(5) . . . . ? N5 Fe1 N7 C17 -20.5(2) . . . . ? N1 Fe1 N7 C17 150.2(2) . . . . ? N4 Fe1 N7 C21 57.98(19) . . . . ? N8 Fe1 N7 C21 -120.5(2) . . . . ? N3 Fe1 N7 C21 89.9(5) . . . . ? N5 Fe1 N7 C21 155.00(19) . . . . ? N1 Fe1 N7 C21 -34.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A S2 0.861(18) 2.526(19) 3.367(2) 165(3) 3_666 N6 H6A S1 0.872(18) 2.481(19) 3.342(2) 170(3) 3_665 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.508 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.082