# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- cif.cif' #==================================================================== # 1. SUBMISSION DETAILS loop_ _publ_contact_author # Name and address of author for correspondence ; Huang, Xiao-Chun Department of Chemistry Shantou University Guangdong 515063 P. R. China ; _publ_contact_author_phone '86 754 82902589' _publ_contact_author_fax '86 754 82902767' _publ_contact_author_email xchuang@stu.edu.cn _publ_requested_coeditor_name ? _publ_contact_letter ; Dear Sir or Madam: Please consider this CIF as a supplmentary data for a paper submitted to Chem. Commun.(CCDC number 856426-856431). Thanks. Xiao-Chun Huang ; #================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #======================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; High-spin versus spin-crossover versus low-spin: symmetry intervention in cooperativity in a 3D polymorphic iron(II)-tetrazole system ; loop_ _publ_author_name _publ_author_address 'Zheng Yan' ; Department of Chemistry Shantou University Guangdong 515063 P. R. China ; 'Mian Li' ; Department of Chemistry Shantou University Guangdong 515063 P. R. China ; 'Hui-Ling Gao' ; Department of Chemistry Shantou University Guangdong 515063 P. R. China ; 'Xiao-Chun Huang' ; Department of Chemistry Shantou University Guangdong 515063 P. R. China ; 'Dan Li' ; Department of Chemistry Shantou University Guangdong 515063 P. R. China ; _publ_contact_author_name 'Xiao-Chun Huang' #====================================== data_complex_1 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 856426' #TrackingRef '- complex_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H7 Fe N12' _chemical_formula_sum 'C12 H7 Fe N12' _chemical_formula_weight 375.15 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fddd _symmetry_space_group_name_Hall -F2uv2vw loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 7.8304(16) _cell_length_b 26.310(5) _cell_length_c 30.543(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6292(2) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2381 _cell_measurement_theta_min 2.668 _cell_measurement_theta_max 26.384 _exptl_crystal_description polyhedron _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3024 _exptl_absorpt_coefficient_mu 0.983 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7635 _exptl_absorpt_correction_T_max 0.8054 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart Apex 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 8307 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1401 _reflns_number_gt 1260 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.0522P)^2^+17.7185P] 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 1401 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0917 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.125 0.125 0.125 129 35 ' ' 2 0.375 -0.125 0.375 129 35 ' ' 3 0.625 0.125 0.625 129 35 ' ' 4 0.875 -0.125 0.875 129 35 ' ' 5 0.875 0.375 0.375 129 35 ' ' 6 0.375 0.375 0.875 129 35 ' ' 7 0.625 0.625 0.125 129 35 ' ' 8 0.125 0.625 0.625 129 35 ' ' _platon_squeeze_details ; ; 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 0.3750 0.3750 0.118112(14) 0.01491(19) Uani 1 2 d S . . C1 C 0.6250 0.51630(13) 0.1250 0.0238(8) Uani 1 2 d S . . C2 C 0.6250 0.57255(13) 0.1250 0.0286(8) Uani 1 2 d S . . C3 C 0.4916(8) 0.59887(19) 0.1068(3) 0.0417(15) Uani 0.50 1 d P . . H3A H 0.3976 0.5808 0.0939 0.050 Uiso 0.50 1 d PR . . C4 C 0.4930(8) 0.6516(2) 0.1067(3) 0.0444(16) Uani 0.50 1 d P . . H4A H 0.3999 0.6699 0.0937 0.053 Uiso 0.50 1 d PR . . C5 C 0.5360(3) 0.29842(9) 0.04028(8) 0.0229(5) Uani 1 1 d . . . C6 C 0.3861(3) 0.27426(10) 0.02046(8) 0.0254(6) Uani 1 1 d . . . C7 C 0.3917(3) 0.22217(11) 0.01237(10) 0.0314(6) Uani 1 1 d . . . H7A H 0.4868 0.2034 0.0209 0.038 Uiso 1 1 d R . . C8 C 0.2430(3) 0.30166(10) 0.00806(9) 0.0320(6) Uani 1 1 d . . . H8A H 0.2379 0.3364 0.0136 0.038 Uiso 1 1 d R . . N1 N 0.5420(2) 0.44004(7) 0.12151(6) 0.0190(4) Uani 1 1 d . . . N2 N 0.4855(3) 0.48757(7) 0.11937(7) 0.0258(5) Uani 1 1 d . . . N3 N 0.5455(2) 0.33339(7) 0.07170(6) 0.0182(4) Uani 1 1 d . . . N4 N 0.7165(2) 0.34061(7) 0.07816(6) 0.0188(4) Uani 1 1 d . . . N5 N 0.8044(3) 0.31237(8) 0.05190(7) 0.0303(5) Uani 1 1 d . . . N6 N 0.6940(3) 0.28553(9) 0.02784(7) 0.0313(5) Uani 1 1 d . . . H6A H 0.7212 0.2628 0.0070 0.038 Uiso 0.50 1 d 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 0.0136(3) 0.0119(3) 0.0192(3) 0.000 0.000 -0.00016(16) C1 0.0216(18) 0.0147(18) 0.0351(19) 0.000 0.0004(14) 0.000 C2 0.026(2) 0.0123(17) 0.048(2) 0.000 -0.0022(16) 0.000 C3 0.034(3) 0.014(3) 0.077(5) -0.006(3) -0.019(3) -0.002(2) C4 0.038(4) 0.017(3) 0.078(5) 0.000(3) -0.016(3) 0.003(2) C5 0.0171(12) 0.0261(13) 0.0255(13) -0.0069(10) -0.0004(10) -0.0007(10) C6 0.0176(13) 0.0305(14) 0.0280(13) -0.0114(11) 0.0002(10) -0.0035(10) C7 0.0207(13) 0.0308(15) 0.0426(16) -0.0120(12) -0.0064(11) 0.0026(10) C8 0.0226(14) 0.0263(14) 0.0470(17) -0.0151(12) -0.0045(12) 0.0002(11) N1 0.0147(9) 0.0122(10) 0.0301(11) 0.0007(8) -0.0002(8) 0.0004(8) N2 0.0210(11) 0.0142(10) 0.0423(13) 0.0021(9) -0.0023(9) 0.0002(8) N3 0.0146(10) 0.0171(10) 0.0229(10) -0.0035(8) 0.0003(8) -0.0019(7) N4 0.0128(10) 0.0212(10) 0.0226(10) -0.0065(8) 0.0001(8) -0.0022(8) N5 0.0195(11) 0.0398(13) 0.0316(12) -0.0194(10) 0.0010(9) -0.0036(10) N6 0.0178(11) 0.0408(13) 0.0353(12) -0.0239(10) 0.0003(9) -0.0011(10) _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 2.1563(19) 2 ? Fe1 N1 2.1563(19) . ? Fe1 N3 2.2340(19) 2 ? Fe1 N3 2.2340(19) . ? Fe1 N4 2.2477(18) 12_454 ? Fe1 N4 2.2477(19) 11_554 ? C1 N2 1.340(3) . ? C1 N2 1.340(3) 11_554 ? C1 C2 1.480(5) . ? C2 C4 1.358(6) 8_554 ? C2 C4 1.358(6) 14 ? C2 C3 1.372(6) 11_554 ? C2 C3 1.372(6) . ? C3 C4 1.387(7) . ? C3 H3A 0.9600 . ? C4 C2 1.358(6) 14 ? C4 H4A 0.9602 . ? C5 N3 1.332(3) . ? C5 N6 1.338(3) . ? C5 C6 1.465(3) . ? C6 C8 1.385(4) . ? C6 C7 1.393(4) . ? C7 C8 1.377(4) 29 ? C7 H7A 0.9301 . ? C8 C7 1.377(4) 29 ? C8 H8A 0.9299 . ? N1 N1 1.317(4) 11_554 ? N1 N2 1.328(3) . ? N3 N4 1.367(3) . ? N4 N5 1.292(3) . ? N4 Fe1 2.2477(18) 11_554 ? N5 N6 1.336(3) . ? N6 H6A 0.8999 . ? 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 174.48(10) 2 . ? N1 Fe1 N3 93.27(7) 2 2 ? N1 Fe1 N3 90.24(7) . 2 ? N1 Fe1 N3 90.24(7) 2 . ? N1 Fe1 N3 93.27(7) . . ? N3 Fe1 N3 101.24(10) 2 . ? N1 Fe1 N4 87.10(7) 2 12_454 ? N1 Fe1 N4 88.87(7) . 12_454 ? N3 Fe1 N4 86.33(7) 2 12_454 ? N3 Fe1 N4 172.12(7) . 12_454 ? N1 Fe1 N4 88.87(7) 2 11_554 ? N1 Fe1 N4 87.10(7) . 11_554 ? N3 Fe1 N4 172.12(7) 2 11_554 ? N3 Fe1 N4 86.33(7) . 11_554 ? N4 Fe1 N4 86.20(10) 12_454 11_554 ? N2 C1 N2 111.3(3) . 11_554 ? N2 C1 C2 124.35(15) . . ? N2 C1 C2 124.35(15) 11_554 . ? C4 C2 C4 119.8(6) 8_554 14 ? C3 C2 C3 119.4(5) 11_554 . ? C4 C2 C1 120.1(3) 8_554 . ? C4 C2 C1 120.1(3) 14 . ? C3 C2 C1 120.3(3) 11_554 . ? C3 C2 C1 120.3(3) . . ? C2 C3 C4 119.9(5) . . ? C4 C3 H3A 114.2 8_554 . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.1 . . ? C2 C4 C3 120.5(5) 14 . ? C3 C4 H4A 114.5 8_554 . ? C2 C4 H4A 119.9 14 . ? C3 C4 H4A 119.7 . . ? N3 C5 N6 109.1(2) . . ? N3 C5 C6 130.0(2) . . ? N6 C5 C6 120.9(2) . . ? C8 C6 C7 119.3(2) . . ? C8 C6 C5 122.4(2) . . ? C7 C6 C5 118.3(2) . . ? C8 C7 C6 120.3(2) 29 . ? C8 C7 H7A 119.9 29 . ? C6 C7 H7A 119.9 . . ? C7 C8 C6 120.5(2) 29 . ? C7 C8 H8A 119.8 29 . ? C6 C8 H8A 119.7 . . ? N1 N1 N2 109.69(12) 11_554 . ? N1 N1 Fe1 127.32(5) 11_554 . ? N2 N1 Fe1 122.86(15) . . ? N1 N2 C1 104.7(2) . . ? C5 N3 N4 104.78(18) . . ? C5 N3 Fe1 139.67(16) . . ? N4 N3 Fe1 115.21(13) . . ? N5 N4 N3 110.64(17) . . ? N5 N4 Fe1 112.99(14) . 11_554 ? N3 N4 Fe1 134.61(14) . 11_554 ? N4 N5 N6 107.49(19) . . ? N5 N6 C5 107.96(19) . . ? N5 N6 H6A 126.0 . . ? C5 N6 H6A 126.0 . . ? 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 N2 C1 C2 C4 37.3(4) . . . 8_554 ? N2 C1 C2 C4 -142.7(4) 11_554 . . 8_554 ? N2 C1 C2 C4 -142.7(4) . . . 14 ? N2 C1 C2 C4 37.3(4) 11_554 . . 14 ? N2 C1 C2 C3 160.9(4) . . . 11_554 ? N2 C1 C2 C3 -19.1(4) 11_554 . . 11_554 ? N2 C1 C2 C3 -19.1(4) . . . . ? N2 C1 C2 C3 160.9(4) 11_554 . . . ? C4 C2 C3 C4 -122.1(6) 14 . . 8_554 ? C3 C2 C3 C4 -75.2(4) 11_554 . . 8_554 ? C1 C2 C3 C4 104.8(4) . . . 8_554 ? C4 C2 C3 C4 75.4(8) 8_554 . . . ? C4 C2 C3 C4 -46.7(7) 14 . . . ? C3 C2 C3 C4 0.3(6) 11_554 . . . ? C1 C2 C3 C4 -179.7(6) . . . . ? C4 C2 C3 C3 41.0(5) 8_554 . . 8_554 ? C4 C2 C3 C3 -81.0(5) 14 . . 8_554 ? C3 C2 C3 C3 -34.1(2) 11_554 . . 8_554 ? C1 C2 C3 C3 145.9(2) . . . 8_554 ? C4 C3 C4 C3 -1.1(9) 8_554 . . 8_554 ? C2 C3 C4 C3 -62.6(9) . . . 8_554 ? C4 C3 C4 C2 61.0(10) 8_554 . . 14 ? C2 C3 C4 C2 -0.5(12) . . . 14 ? C3 C3 C4 C2 62.1(6) 8_554 . . 14 ? C2 C3 C4 C4 -61.5(6) . . . 8_554 ? C3 C3 C4 C4 1.1(9) 8_554 . . 8_554 ? N3 C5 C6 C8 44.6(4) . . . . ? N6 C5 C6 C8 -136.7(3) . . . . ? N3 C5 C6 C7 -137.9(3) . . . . ? N6 C5 C6 C7 40.7(4) . . . . ? C8 C6 C7 C8 0.6(5) . . . 29 ? C5 C6 C7 C8 -176.9(3) . . . 29 ? C7 C6 C8 C7 -0.6(5) . . . 29 ? C5 C6 C8 C7 176.8(3) . . . 29 ? N1 Fe1 N1 N1 80.4(2) 2 . . 11_554 ? N3 Fe1 N1 N1 -150.2(3) 2 . . 11_554 ? N3 Fe1 N1 N1 -48.9(3) . . . 11_554 ? N4 Fe1 N1 N1 123.5(3) 12_454 . . 11_554 ? N4 Fe1 N1 N1 37.2(3) 11_554 . . 11_554 ? N1 Fe1 N1 N2 -95.16(17) 2 . . . ? N3 Fe1 N1 N2 34.26(18) 2 . . . ? N3 Fe1 N1 N2 135.53(17) . . . . ? N4 Fe1 N1 N2 -52.06(18) 12_454 . . . ? N4 Fe1 N1 N2 -138.32(18) 11_554 . . . ? N1 N1 N2 C1 0.5(3) 11_554 . . . ? Fe1 N1 N2 C1 176.74(11) . . . . ? N2 C1 N2 N1 -0.18(10) 11_554 . . . ? C2 C1 N2 N1 179.82(10) . . . . ? N6 C5 N3 N4 -0.8(3) . . . . ? C6 C5 N3 N4 178.0(2) . . . . ? N6 C5 N3 Fe1 -173.25(18) . . . . ? C6 C5 N3 Fe1 5.5(4) . . . . ? N1 Fe1 N3 C5 31.7(3) 2 . . . ? N1 Fe1 N3 C5 -152.6(3) . . . . ? N3 Fe1 N3 C5 -61.7(2) 2 . . . ? N4 Fe1 N3 C5 101.8(5) 12_454 . . . ? N4 Fe1 N3 C5 120.5(3) 11_554 . . . ? N1 Fe1 N3 N4 -140.28(15) 2 . . . ? N1 Fe1 N3 N4 35.45(15) . . . . ? N3 Fe1 N3 N4 126.34(16) 2 . . . ? N4 Fe1 N3 N4 -70.1(5) 12_454 . . . ? N4 Fe1 N3 N4 -51.43(13) 11_554 . . . ? C5 N3 N4 N5 0.8(3) . . . . ? Fe1 N3 N4 N5 175.47(16) . . . . ? C5 N3 N4 Fe1 -162.42(17) . . . 11_554 ? Fe1 N3 N4 Fe1 12.2(2) . . . 11_554 ? N3 N4 N5 N6 -0.6(3) . . . . ? Fe1 N4 N5 N6 166.56(16) 11_554 . . . ? N4 N5 N6 C5 0.1(3) . . . . ? N3 C5 N6 N5 0.5(3) . . . . ? C6 C5 N6 N5 -178.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.464 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.068 #===============================END data_complex_1a #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 856427' #TrackingRef '- complex_1'.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H7 Fe N12' _chemical_formula_sum 'C12 H7 Fe N12' _chemical_formula_weight 375.15 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fddd _symmetry_space_group_name_Hall -F2uv2vw loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 7.7980(3) _cell_length_b 26.3062(14) _cell_length_c 30.3991(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6235.9(5) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1975 _cell_measurement_theta_min 2.800 _cell_measurement_theta_max 29.330 _exptl_crystal_description polyhedron _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3024 _exptl_absorpt_coefficient_mu 0.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.812 _exptl_absorpt_correction_T_max 0.845 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 Smart Apex 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 4775 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1384 _reflns_number_gt 1160 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.0251P)^2^+27.6955P] 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 1384 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0719 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.625 0.125 0.125 117 38 ' ' 2 0.125 0.125 0.625 117 38 ' ' 3 0.375 0.375 0.375 117 38 ' ' 4 0.875 0.375 0.875 117 38 ' ' 5 0.125 0.625 0.125 117 38 ' ' 6 0.625 0.625 0.625 117 38 ' ' 7 0.875 0.875 0.375 117 38 ' ' 8 0.375 0.875 0.875 117 38 ' ' _platon_squeeze_details ; ; 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 0.3750 0.3750 0.117810(15) 0.00596(16) Uani 1 2 d S . . N1 N 0.5411(2) 0.43986(7) 0.12150(6) 0.0085(4) Uani 1 1 d . . . N2 N 0.4844(3) 0.48766(8) 0.11931(7) 0.0117(5) Uani 1 1 d . . . N3 N 0.5313(2) 0.34079(8) 0.17167(6) 0.0085(5) Uani 1 1 d . . . N4 N 0.4434(3) 0.31228(8) 0.19811(7) 0.0133(5) Uani 1 1 d . . . N5 N 0.5542(3) 0.28535(8) 0.22214(7) 0.0138(5) Uani 1 1 d . . . H5A H 0.5270 0.2625 0.2430 0.017 Uiso 0.50 1 d PR . . N6 N 0.7037(2) 0.33346(8) 0.17807(6) 0.0080(5) Uani 1 1 d . . . C1 C 0.6250 0.51647(13) 0.1250 0.0103(7) Uani 1 2 d S . . C2 C 0.6250 0.57225(14) 0.1250 0.0133(8) Uani 1 2 d S . . C3 C 0.4915(7) 0.5992(2) 0.10570(19) 0.0192(13) Uani 0.50 1 d P . . H3A H 0.3978 0.5811 0.0925 0.023 Uiso 0.50 1 d PR . . C4 C 0.4921(7) 0.6513(2) 0.10538(19) 0.0187(12) Uani 0.50 1 d P . . H4A H 0.4001 0.6695 0.0915 0.022 Uiso 0.50 1 d PR . . C5 C 0.7126(3) 0.29832(10) 0.20974(8) 0.0100(5) Uani 1 1 d . . . C6 C 0.8639(3) 0.27427(10) 0.22949(8) 0.0116(6) Uani 1 1 d . . . C7 C 1.0065(3) 0.30207(10) 0.24204(8) 0.0141(6) Uani 1 1 d . . . H7A H 1.0111 0.3380 0.2365 0.017 Uiso 1 1 d R . . C8 C 0.8577(3) 0.22201(10) 0.23748(8) 0.0150(6) Uani 1 1 d . . . H8A H 0.7588 0.2028 0.2287 0.018 Uiso 1 1 d 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 0.0064(3) 0.0043(3) 0.0072(3) 0.000 0.000 0.0003(2) N1 0.0093(9) 0.0039(11) 0.0122(10) -0.0001(8) -0.0003(8) 0.0019(9) N2 0.0125(11) 0.0035(11) 0.0190(11) 0.0009(9) -0.0007(9) -0.0003(9) N3 0.0061(10) 0.0098(12) 0.0096(10) 0.0012(8) 0.0019(8) 0.0011(9) N4 0.0109(11) 0.0165(13) 0.0126(11) 0.0078(9) 0.0006(9) 0.0014(10) N5 0.0081(11) 0.0172(13) 0.0161(11) 0.0107(9) -0.0011(9) 0.0014(10) N6 0.0066(10) 0.0070(11) 0.0104(10) 0.0023(8) 0.0000(8) 0.0026(9) C1 0.0121(18) 0.0058(19) 0.0130(17) 0.000 -0.0013(14) 0.000 C2 0.0142(18) 0.0058(19) 0.0198(19) 0.000 0.0001(15) 0.000 C3 0.018(3) 0.007(3) 0.032(4) -0.002(2) -0.011(2) -0.004(2) C4 0.021(3) 0.006(3) 0.030(4) 0.003(2) -0.006(2) 0.002(2) C5 0.0088(12) 0.0110(14) 0.0103(12) 0.0027(10) -0.0006(10) -0.0002(11) C6 0.0080(12) 0.0157(15) 0.0111(12) 0.0069(10) 0.0015(10) 0.0015(11) C7 0.0115(13) 0.0102(14) 0.0208(14) 0.0090(11) -0.0016(11) -0.0012(11) C8 0.0097(13) 0.0155(15) 0.0198(14) 0.0066(11) -0.0022(11) -0.0022(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 N1 2.145(2) . ? Fe1 N1 2.145(2) 2 ? Fe1 N6 2.2189(19) 12_454 ? Fe1 N6 2.219(2) 11_554 ? Fe1 N3 2.231(2) . ? Fe1 N3 2.231(2) 2 ? N1 N1 1.325(4) 11_554 ? N1 N2 1.335(3) . ? N2 C1 1.344(3) . ? N3 N4 1.296(3) . ? N3 N6 1.372(3) . ? N4 N5 1.335(3) . ? N5 C5 1.335(3) . ? N5 H5A 0.9000 . ? N6 C5 1.337(3) . ? N6 Fe1 2.2189(19) 11_554 ? C1 N2 1.344(3) 11_554 ? C1 C2 1.467(5) . ? C2 C4 1.383(6) 14 ? C2 C4 1.383(6) 8_554 ? C2 C3 1.389(6) 11_554 ? C2 C3 1.389(6) . ? C3 C4 1.372(7) . ? C3 H3A 0.9601 . ? C4 C2 1.383(6) 14 ? C4 H4A 0.9600 . ? C5 C6 1.467(3) . ? C6 C7 1.385(4) . ? C6 C8 1.397(4) . ? C7 C8 1.382(4) 21_755 ? C7 H7A 0.9601 . ? C8 C7 1.382(4) 21_755 ? C8 H8A 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 174.00(10) . 2 ? N1 Fe1 N6 90.27(7) . 12_454 ? N1 Fe1 N6 93.50(7) 2 12_454 ? N1 Fe1 N6 93.50(7) . 11_554 ? N1 Fe1 N6 90.27(7) 2 11_554 ? N6 Fe1 N6 102.11(10) 12_454 11_554 ? N1 Fe1 N3 87.28(7) . . ? N1 Fe1 N3 88.32(7) 2 . ? N6 Fe1 N3 171.46(8) 12_454 . ? N6 Fe1 N3 86.20(7) 11_554 . ? N1 Fe1 N3 88.32(7) . 2 ? N1 Fe1 N3 87.28(7) 2 2 ? N6 Fe1 N3 86.20(7) 12_454 2 ? N6 Fe1 N3 171.46(8) 11_554 2 ? N3 Fe1 N3 85.55(10) . 2 ? N1 N1 N2 109.60(12) 11_554 . ? N1 N1 Fe1 127.19(5) 11_554 . ? N2 N1 Fe1 123.11(15) . . ? N1 N2 C1 104.7(2) . . ? N4 N3 N6 110.44(18) . . ? N4 N3 Fe1 113.56(15) . . ? N6 N3 Fe1 134.11(15) . . ? N3 N4 N5 107.68(19) . . ? C5 N5 N4 108.00(19) . . ? C5 N5 H5A 126.0 . . ? N4 N5 H5A 126.0 . . ? C5 N6 N3 104.47(19) . . ? C5 N6 Fe1 139.67(16) . 11_554 ? N3 N6 Fe1 115.57(14) . 11_554 ? N2 C1 N2 111.4(3) . 11_554 ? N2 C1 C2 124.32(15) . . ? N2 C1 C2 124.32(15) 11_554 . ? C4 C2 C4 119.7(5) 14 8_554 ? C3 C2 C3 118.6(5) 11_554 . ? C4 C2 C1 120.2(3) 14 . ? C4 C2 C1 120.2(3) 8_554 . ? C3 C2 C1 120.7(3) 11_554 . ? C3 C2 C1 120.7(3) . . ? C4 C3 C2 120.7(5) . . ? C4 C3 H3A 114.6 8_554 . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C3 C4 C2 120.1(5) . 14 ? C3 C4 H4A 116.3 8_554 . ? C3 C4 H4A 119.9 . . ? C2 C4 H4A 119.9 14 . ? N5 C5 N6 109.4(2) . . ? N5 C5 C6 121.2(2) . . ? N6 C5 C6 129.4(2) . . ? C7 C6 C8 120.0(2) . . ? C7 C6 C5 122.1(2) . . ? C8 C6 C5 117.9(2) . . ? C8 C7 C6 119.8(2) 21_755 . ? C8 C7 H7A 120.1 21_755 . ? C6 C7 H7A 120.1 . . ? C7 C8 C6 120.2(2) 21_755 . ? C7 C8 H8A 119.9 21_755 . ? C6 C8 H8A 119.9 . . ? 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 N1 80.7(2) 2 . . 11_554 ? N6 Fe1 N1 N1 -150.3(3) 12_454 . . 11_554 ? N6 Fe1 N1 N1 -48.2(3) 11_554 . . 11_554 ? N3 Fe1 N1 N1 37.8(3) . . . 11_554 ? N3 Fe1 N1 N1 123.5(3) 2 . . 11_554 ? N1 Fe1 N1 N2 -95.38(17) 2 . . . ? N6 Fe1 N1 N2 33.61(17) 12_454 . . . ? N6 Fe1 N1 N2 135.76(17) 11_554 . . . ? N3 Fe1 N1 N2 -138.21(18) . . . . ? N3 Fe1 N1 N2 -52.59(17) 2 . . . ? N1 N1 N2 C1 0.4(3) 11_554 . . . ? Fe1 N1 N2 C1 177.05(11) . . . . ? N1 Fe1 N3 N4 146.85(17) . . . . ? N1 Fe1 N3 N4 -29.07(17) 2 . . . ? N6 Fe1 N3 N4 73.4(5) 12_454 . . . ? N6 Fe1 N3 N4 -119.46(17) 11_554 . . . ? N3 Fe1 N3 N4 58.33(14) 2 . . . ? N1 Fe1 N3 N6 -50.7(2) . . . . ? N1 Fe1 N3 N6 133.4(2) 2 . . . ? N6 Fe1 N3 N6 -124.2(4) 12_454 . . . ? N6 Fe1 N3 N6 43.00(19) 11_554 . . . ? N3 Fe1 N3 N6 -139.2(3) 2 . . . ? N6 N3 N4 N5 -0.5(3) . . . . ? Fe1 N3 N4 N5 166.15(15) . . . . ? N3 N4 N5 C5 0.2(3) . . . . ? N4 N3 N6 C5 0.6(3) . . . . ? Fe1 N3 N6 C5 -162.23(18) . . . . ? N4 N3 N6 Fe1 175.66(15) . . . 11_554 ? Fe1 N3 N6 Fe1 12.8(3) . . . 11_554 ? N1 N2 C1 N2 -0.14(10) . . . 11_554 ? N1 N2 C1 C2 179.86(10) . . . . ? N2 C1 C2 C4 -141.1(3) . . . 14 ? N2 C1 C2 C4 38.9(3) 11_554 . . 14 ? N2 C1 C2 C4 38.9(3) . . . 8_554 ? N2 C1 C2 C4 -141.1(3) 11_554 . . 8_554 ? N2 C1 C2 C3 159.6(3) . . . 11_554 ? N2 C1 C2 C3 -20.4(3) 11_554 . . 11_554 ? N2 C1 C2 C3 -20.4(3) . . . . ? N2 C1 C2 C3 159.6(3) 11_554 . . . ? C4 C2 C3 C4 -123.0(5) 14 . . 8_554 ? C3 C2 C3 C4 -74.4(4) 11_554 . . 8_554 ? C1 C2 C3 C4 105.6(4) . . . 8_554 ? C4 C2 C3 C4 -48.0(5) 14 . . . ? C4 C2 C3 C4 75.0(6) 8_554 . . . ? C3 C2 C3 C4 0.5(4) 11_554 . . . ? C1 C2 C3 C4 -179.5(4) . . . . ? C4 C2 C3 C3 -83.5(4) 14 . . 8_554 ? C4 C2 C3 C3 39.5(4) 8_554 . . 8_554 ? C3 C2 C3 C3 -35.0(2) 11_554 . . 8_554 ? C1 C2 C3 C3 145.0(2) . . . 8_554 ? C4 C3 C4 C3 -0.4(7) 8_554 . . 8_554 ? C2 C3 C4 C3 -61.1(7) . . . 8_554 ? C4 C3 C4 C2 59.6(7) 8_554 . . 14 ? C2 C3 C4 C2 -1.1(8) . . . 14 ? C3 C3 C4 C2 60.0(4) 8_554 . . 14 ? C2 C3 C4 C4 -60.6(5) . . . 8_554 ? C3 C3 C4 C4 0.4(7) 8_554 . . 8_554 ? N4 N5 C5 N6 0.2(3) . . . . ? N4 N5 C5 C6 -178.5(2) . . . . ? N3 N6 C5 N5 -0.5(3) . . . . ? Fe1 N6 C5 N5 -173.57(18) 11_554 . . . ? N3 N6 C5 C6 178.1(2) . . . . ? Fe1 N6 C5 C6 5.1(4) 11_554 . . . ? N5 C5 C6 C7 -136.4(3) . . . . ? N6 C5 C6 C7 45.1(4) . . . . ? N5 C5 C6 C8 40.5(3) . . . . ? N6 C5 C6 C8 -138.0(3) . . . . ? C8 C6 C7 C8 -0.1(4) . . . 21_755 ? C5 C6 C7 C8 176.8(2) . . . 21_755 ? C7 C6 C8 C7 0.1(4) . . . 21_755 ? C5 C6 C8 C7 -176.9(2) . . . 21_755 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.434 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.069 #===============================END data_complex_2 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 856428' #TrackingRef '- complex_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H7 Fe N12' _chemical_formula_sum 'C12 H7 Fe N12' _chemical_formula_weight 375.15 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M R-3m _symmetry_space_group_name_Hall -R32 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z' 'x-y, -y, -z' '-x, -x+y, -z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+1/3' 'x-y+2/3, -y+1/3, -z+1/3' '-x+2/3, -x+y+1/3, -z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+2/3' 'x-y+1/3, -y+2/3, -z+2/3' '-x+1/3, -x+y+2/3, -z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z+1/3' '-x+y+2/3, y+1/3, z+1/3' 'x+2/3, x-y+1/3, z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+2/3' '-x+y+1/3, y+2/3, z+2/3' 'x+1/3, x-y+2/3, z+2/3' _cell_length_a 22.604(4) _cell_length_b 22.604(4) _cell_length_c 7.454(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3298(2) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1405 _cell_measurement_theta_min 2.925 _cell_measurement_theta_max 24.439 _exptl_crystal_description polyhedron _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1134 _exptl_absorpt_coefficient_mu 0.704 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.839 _exptl_absorpt_correction_T_max 0.887 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart Apex 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 4664 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 24.99 _reflns_number_total 709 _reflns_number_gt 641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.0739P)^2^+8.9736P] 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 709 _refine_ls_number_parameters 59 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1165 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.007 0.300 -0.090 1323 436 ' ' _platon_squeeze_details ; ; 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 0.3333 0.6667 0.1667 0.0099(3) Uani 1 12 d S . . Fe2 Fe 0.3333 0.6667 0.6667 0.0118(3) Uani 1 12 d S . . N1 N 0.25615(8) 0.51231(16) 0.5350(4) 0.0376(9) Uani 1 2 d S . . H1A H 0.2472 0.4944 0.6462 0.045 Uiso 0.33 2 d SPR . . N2 N 0.28931(7) 0.57862(14) 0.4897(4) 0.0228(7) Uani 1 2 d S . . N3 N 0.29163(7) 0.58326(14) 0.3129(3) 0.0153(6) Uani 1 2 d S . . N4 N 0.26066(7) 0.52131(14) 0.2396(4) 0.0228(7) Uani 1 2 d S . . C1 C 0.23950(10) 0.47899(19) 0.3799(5) 0.0332(10) Uani 1 2 d S . . C2 C 0.20186(10) 0.40371(19) 0.3580(5) 0.0397(11) Uani 1 2 d S . . C3 C 0.1552(4) 0.3751(3) 0.2201(9) 0.060(2) Uani 0.50 1 d P . . H3 H 0.1470 0.4038 0.1412 0.072 Uiso 0.50 1 d PR . . C4 C 0.2124(4) 0.3622(3) 0.4735(9) 0.062(2) Uani 0.50 1 d P . . H4 H 0.2432 0.3818 0.5728 0.075 Uiso 0.50 1 d 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 0.0095(4) 0.0095(4) 0.0107(6) 0.000 0.000 0.0047(2) Fe2 0.0121(4) 0.0121(4) 0.0111(6) 0.000 0.000 0.0060(2) N1 0.064(2) 0.0138(16) 0.0179(16) 0.0044(12) 0.0022(6) 0.0069(8) N2 0.0339(13) 0.0142(14) 0.0139(14) 0.0010(11) 0.0005(6) 0.0071(7) N3 0.0179(10) 0.0137(13) 0.0129(13) -0.0003(10) -0.0002(5) 0.0068(7) N4 0.0323(13) 0.0094(13) 0.0191(15) -0.0017(11) -0.0009(5) 0.0047(7) C1 0.050(2) 0.0136(18) 0.0233(19) 0.0010(15) 0.0005(7) 0.0068(9) C2 0.068(3) 0.0135(18) 0.0201(19) -0.0001(15) -0.0001(7) 0.0068(9) C3 0.101(6) 0.014(3) 0.044(4) 0.005(3) -0.020(4) 0.013(3) C4 0.102(6) 0.017(3) 0.041(4) -0.002(3) -0.029(3) 0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N3 1.963(3) 27 ? Fe1 N3 1.963(3) 3_565 ? Fe1 N3 1.963(3) 2_665 ? Fe1 N3 1.963(3) . ? Fe1 N3 1.963(3) 26_455 ? Fe1 N3 1.963(3) 25_565 ? Fe2 N2 2.170(3) 27_556 ? Fe2 N2 2.170(3) 3_565 ? Fe2 N2 2.170(3) . ? Fe2 N2 2.170(3) 2_665 ? Fe2 N2 2.170(3) 25_566 ? Fe2 N2 2.170(3) 26_456 ? N1 C1 1.327(5) . ? N1 N2 1.341(4) . ? N1 H1A 0.9000 . ? N2 N3 1.321(4) . ? N3 N4 1.330(4) . ? N4 C1 1.334(5) . ? C1 C2 1.483(5) . ? C2 C3 1.379(8) . ? C2 C3 1.379(8) 23 ? C2 C4 1.379(7) 23 ? C2 C4 1.379(7) . ? C3 C4 1.398(8) 31 ? C3 H3 0.9598 . ? C4 C3 1.398(8) 31 ? C4 H4 0.9601 . ? 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 180.00(6) 27 3_565 ? N3 Fe1 N3 87.85(11) 27 2_665 ? N3 Fe1 N3 92.15(11) 3_565 2_665 ? N3 Fe1 N3 87.85(11) 27 . ? N3 Fe1 N3 92.15(11) 3_565 . ? N3 Fe1 N3 92.15(11) 2_665 . ? N3 Fe1 N3 92.15(11) 27 26_455 ? N3 Fe1 N3 87.85(11) 3_565 26_455 ? N3 Fe1 N3 179.997(1) 2_665 26_455 ? N3 Fe1 N3 87.86(11) . 26_455 ? N3 Fe1 N3 92.15(11) 27 25_565 ? N3 Fe1 N3 87.85(11) 3_565 25_565 ? N3 Fe1 N3 87.86(11) 2_665 25_565 ? N3 Fe1 N3 180.0 . 25_565 ? N3 Fe1 N3 92.14(11) 26_455 25_565 ? N2 Fe2 N2 180.0 27_556 3_565 ? N2 Fe2 N2 93.10(11) 27_556 . ? N2 Fe2 N2 86.90(11) 3_565 . ? N2 Fe2 N2 93.10(11) 27_556 2_665 ? N2 Fe2 N2 86.90(11) 3_565 2_665 ? N2 Fe2 N2 86.90(11) . 2_665 ? N2 Fe2 N2 86.90(11) 27_556 25_566 ? N2 Fe2 N2 93.10(11) 3_565 25_566 ? N2 Fe2 N2 179.998(1) . 25_566 ? N2 Fe2 N2 93.10(11) 2_665 25_566 ? N2 Fe2 N2 86.90(11) 27_556 26_456 ? N2 Fe2 N2 93.10(11) 3_565 26_456 ? N2 Fe2 N2 93.10(11) . 26_456 ? N2 Fe2 N2 180.00(11) 2_665 26_456 ? N2 Fe2 N2 86.90(11) 25_566 26_456 ? C1 N1 N2 104.9(3) . . ? C1 N1 H1A 127.6 . . ? N2 N1 H1A 127.5 . . ? N3 N2 N1 108.5(3) . . ? N3 N2 Fe2 123.5(2) . . ? N1 N2 Fe2 128.0(2) . . ? N2 N3 N4 110.3(3) . . ? N2 N3 Fe1 127.7(2) . . ? N4 N3 Fe1 122.0(2) . . ? N3 N4 C1 104.1(3) . . ? N1 C1 N4 112.2(3) . . ? N1 C1 C2 125.8(3) . . ? N4 C1 C2 122.1(3) . . ? C3 C2 C4 119.8(5) 23 23 ? C3 C2 C4 119.8(5) . . ? C3 C2 C1 119.0(4) . . ? C3 C2 C1 119.0(4) 23 . ? C4 C2 C1 121.1(4) 23 . ? C4 C2 C1 121.1(4) . . ? C2 C3 C4 120.0(6) . 31 ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.0 31 . ? C2 C4 C3 120.1(6) . 31 ? C2 C4 H4 119.9 . . ? C3 C4 H4 120.0 31 . ? C4 C4 H4 119.7 23 . ? 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 C1 N1 N2 N3 0.000(2) . . . . ? C1 N1 N2 Fe2 180.0 . . . . ? N2 Fe2 N2 N3 -136.47(5) 27_556 . . . ? N2 Fe2 N2 N3 43.53(5) 3_565 . . . ? N2 Fe2 N2 N3 -43.53(5) 2_665 . . . ? N2 Fe2 N2 N3 80(13) 25_566 . . . ? N2 Fe2 N2 N3 136.47(5) 26_456 . . . ? N2 Fe2 N2 N1 43.53(5) 27_556 . . . ? N2 Fe2 N2 N1 -136.47(5) 3_565 . . . ? N2 Fe2 N2 N1 136.47(5) 2_665 . . . ? N2 Fe2 N2 N1 -100(13) 25_566 . . . ? N2 Fe2 N2 N1 -43.53(5) 26_456 . . . ? N1 N2 N3 N4 0.000(2) . . . . ? Fe2 N2 N3 N4 180.000(1) . . . . ? N1 N2 N3 Fe1 180.000(1) . . . . ? Fe2 N2 N3 Fe1 0.000(1) . . . . ? N3 Fe1 N3 N2 133.89(6) 27 . . . ? N3 Fe1 N3 N2 -46.11(6) 3_565 . . . ? N3 Fe1 N3 N2 46.11(6) 2_665 . . . ? N3 Fe1 N3 N2 -133.88(6) 26_455 . . . ? N3 Fe1 N3 N2 -64(5) 25_565 . . . ? N3 Fe1 N3 N4 -46.11(6) 27 . . . ? N3 Fe1 N3 N4 133.89(6) 3_565 . . . ? N3 Fe1 N3 N4 -133.89(6) 2_665 . . . ? N3 Fe1 N3 N4 46.12(6) 26_455 . . . ? N3 Fe1 N3 N4 116(5) 25_565 . . . ? N2 N3 N4 C1 0.000(2) . . . . ? Fe1 N3 N4 C1 180.000(1) . . . . ? N2 N1 C1 N4 0.000(2) . . . . ? N2 N1 C1 C2 180.000(2) . . . . ? N3 N4 C1 N1 0.000(2) . . . . ? N3 N4 C1 C2 180.000(1) . . . . ? N1 C1 C2 C3 142.7(5) . . . . ? N4 C1 C2 C3 -37.3(5) . . . . ? N1 C1 C2 C3 -142.7(5) . . . 23 ? N4 C1 C2 C3 37.3(5) . . . 23 ? N1 C1 C2 C4 36.8(5) . . . 23 ? N4 C1 C2 C4 -143.2(5) . . . 23 ? N1 C1 C2 C4 -36.8(5) . . . . ? N4 C1 C2 C4 143.2(5) . . . . ? C3 C2 C3 C4 67.5(8) 23 . . 31 ? C4 C2 C3 C4 -57.7(7) 23 . . 31 ? C4 C2 C3 C4 -2.7(12) . . . 31 ? C1 C2 C3 C4 177.8(6) . . . 31 ? C4 C2 C3 C3 -125.2(4) 23 . . 23 ? C4 C2 C3 C3 -70.2(5) . . . 23 ? C1 C2 C3 C3 110.3(4) . . . 23 ? C3 C2 C3 C4 125.2(4) 23 . . 23 ? C4 C2 C3 C4 55.0(7) . . . 23 ? C1 C2 C3 C4 -124.5(4) . . . 23 ? C3 C2 C3 C4 33.9(4) 23 . . 17 ? C4 C2 C3 C4 -91.3(5) 23 . . 17 ? C4 C2 C3 C4 -36.3(6) . . . 17 ? C1 C2 C3 C4 144.2(3) . . . 17 ? C3 C2 C4 C3 2.8(12) . . . 31 ? C3 C2 C4 C3 -55.1(7) 23 . . 31 ? C4 C2 C4 C3 71.1(8) 23 . . 31 ? C1 C2 C4 C3 -177.8(6) . . . 31 ? C3 C2 C4 C4 -68.4(5) . . . 23 ? C3 C2 C4 C4 -126.2(4) 23 . . 23 ? C1 C2 C4 C4 111.1(4) . . . 23 ? C3 C2 C4 C3 57.8(8) . . . 23 ? C4 C2 C4 C3 126.2(4) 23 . . 23 ? C1 C2 C4 C3 -122.7(4) . . . 23 ? C3 C2 C4 C3 -33.6(6) . . . 17 ? C3 C2 C4 C3 -91.4(5) 23 . . 17 ? C4 C2 C4 C3 34.8(4) 23 . . 17 ? C1 C2 C4 C3 145.9(3) . . . 17 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.466 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.070 #===============================END data_complex_2a #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 856429' #TrackingRef '- complex_2'.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H7 Fe N12' _chemical_formula_sum 'C12 H7 Fe N12' _chemical_formula_weight 375.15 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' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall -R3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 22.4652(8) _cell_length_b 22.4652(8) _cell_length_c 7.3495(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3212.3(3) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1471 _cell_measurement_theta_min 2.957 _cell_measurement_theta_max 29.466 _exptl_crystal_description polyhedron _exptl_crystal_colour black _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1134 _exptl_absorpt_coefficient_mu 0.722 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.835 _exptl_absorpt_correction_T_max 0.884 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 Smart Apex 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 2974 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 26.99 _reflns_number_total 1561 _reflns_number_gt 1261 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.0503P)^2^+9.1608P] 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 1561 _refine_ls_number_parameters 78 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.333 -0.037 85 25 ' ' 2 0.000 0.667 -0.038 85 26 ' ' 3 0.333 0.000 -0.037 85 25 ' ' 4 0.333 0.333 -0.039 85 26 ' ' 5 0.667 0.667 -0.037 85 25 ' ' 6 0.667 1.000 -0.038 85 26 ' ' 7 0.454 0.223 0.147 24 9 ' ' 8 0.777 0.231 0.147 23 9 ' ' 9 0.769 0.546 0.147 23 9 ' ' 10 0.213 0.110 0.186 22 9 ' ' 11 0.889 0.102 0.186 23 9 ' ' 12 0.897 0.787 0.186 23 9 ' ' 13 0.120 0.556 0.480 23 9 ' ' 14 0.444 0.564 0.480 22 9 ' ' 15 0.436 0.880 0.480 22 9 ' ' 16 0.556 0.436 0.520 22 9 ' ' 17 0.564 0.120 0.519 23 9 ' ' 18 0.880 0.444 0.519 22 9 ' ' 19 0.102 0.213 0.813 22 9 ' ' 20 0.110 0.897 0.814 23 9 ' ' 21 0.787 0.889 0.813 24 9 ' ' 22 0.223 0.769 0.853 23 9 ' ' 23 0.231 0.454 0.853 23 9 ' ' 24 0.546 0.777 0.853 23 9 ' ' _platon_squeeze_details ; ; 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 Fe2 Fe 0.0000 0.0000 0.0000 0.0075(2) Uani 1 6 d S . . Fe1 Fe 0.0000 0.0000 0.5000 0.0069(2) Uani 1 6 d S . . N4 N 0.07260(11) 0.14533(10) 0.4234(3) 0.0178(5) Uani 1 1 d . . . N3 N 0.04137(10) 0.08258(10) 0.3496(3) 0.0115(4) Uani 1 1 d . . . N2 N 0.04327(11) 0.08655(11) 0.1706(3) 0.0165(5) Uani 1 1 d . . . N1 N 0.07638(13) 0.15293(11) 0.1231(3) 0.0257(6) Uani 1 1 d . . . H1A H 0.0850 0.1704 0.0097 0.031 Uiso 0.33 1 d PR . . C1 C 0.09381(15) 0.18757(14) 0.2789(4) 0.0252(6) Uani 1 1 d . . . C2 C 0.13154(18) 0.26284(14) 0.3040(4) 0.0314(7) Uani 1 1 d . . . C3 C 0.1120(4) 0.2908(3) 0.4412(10) 0.0473(10) Uani 0.522(4) 1 d P . 1 H3 H 0.0731 0.2611 0.5155 0.057 Uiso 0.522(4) 1 d PR . 1 C4 C 0.1859(4) 0.3048(3) 0.1922(10) 0.0473(10) Uani 0.522(4) 1 d P . 1 H4 H 0.1987 0.2856 0.0932 0.057 Uiso 0.522(4) 1 d PR . 1 C3' C 0.1204(4) 0.3053(3) 0.1956(11) 0.0473(10) Uani 0.478(4) 1 d P . . H3' H 0.0882 0.2866 0.0970 0.057 Uiso 0.478(4) 1 d PR . . C4' C 0.1776(4) 0.2904(3) 0.4380(11) 0.0473(10) Uani 0.478(4) 1 d P . . H4' H 0.1867 0.2609 0.5131 0.057 Uiso 0.478(4) 1 d 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 Fe2 0.0051(3) 0.0051(3) 0.0121(4) 0.000 0.000 0.00256(13) Fe1 0.0042(3) 0.0042(3) 0.0122(4) 0.000 0.000 0.00210(13) N4 0.0186(11) 0.0057(10) 0.0250(12) 0.0024(8) 0.0013(9) 0.0031(8) N3 0.0105(10) 0.0063(9) 0.0167(10) 0.0018(8) 0.0013(8) 0.0035(8) N2 0.0183(11) 0.0096(10) 0.0195(11) 0.0056(8) 0.0030(9) 0.0055(9) N1 0.0355(14) 0.0123(11) 0.0219(12) 0.0073(9) 0.0047(10) 0.0065(10) C1 0.0279(15) 0.0106(13) 0.0313(15) 0.0067(11) 0.0036(12) 0.0052(11) C2 0.0443(19) 0.0113(13) 0.0278(15) 0.0048(11) 0.0037(13) 0.0057(13) C3 0.061(2) 0.0120(15) 0.051(2) 0.0072(14) -0.0017(19) 0.0052(16) C4 0.061(2) 0.0120(15) 0.051(2) 0.0072(14) -0.0017(19) 0.0052(16) C3' 0.061(2) 0.0120(15) 0.051(2) 0.0072(14) -0.0017(19) 0.0052(16) C4' 0.061(2) 0.0120(15) 0.051(2) 0.0072(14) -0.0017(19) 0.0052(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe2 N2 2.099(2) 10 ? Fe2 N2 2.099(2) . ? Fe2 N2 2.099(2) 12 ? Fe2 N2 2.099(2) 3 ? Fe2 N2 2.099(2) 2 ? Fe2 N2 2.099(2) 11 ? Fe1 N3 1.9502(19) 2 ? Fe1 N3 1.9502(19) 11_556 ? Fe1 N3 1.9502(19) 3 ? Fe1 N3 1.9502(19) . ? Fe1 N3 1.9502(19) 10_556 ? Fe1 N3 1.9502(19) 12_556 ? N4 N3 1.336(3) . ? N4 C1 1.343(3) . ? N3 N2 1.318(3) . ? N2 N1 1.338(3) . ? N1 C1 1.329(4) . ? N1 H1A 0.9000 . ? C1 C2 1.476(4) . ? C2 C4' 1.335(9) . ? C2 C3' 1.359(8) . ? C2 C3 1.371(8) . ? C2 C4 1.380(8) . ? C3 C4 1.405(8) 16 ? C3 H3 0.9600 . ? C4 C3 1.405(8) 16 ? C4 H4 0.9600 . ? C3' C4' 1.401(9) 16 ? C3' H3' 0.9600 . ? C4' C3' 1.401(9) 16 ? C4' H4' 0.9602 . ? 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 N2 Fe2 N2 180.00(14) 10 . ? N2 Fe2 N2 88.00(8) 10 12 ? N2 Fe2 N2 92.00(8) . 12 ? N2 Fe2 N2 92.00(8) 10 3 ? N2 Fe2 N2 88.00(8) . 3 ? N2 Fe2 N2 180.00(14) 12 3 ? N2 Fe2 N2 92.00(8) 10 2 ? N2 Fe2 N2 88.00(8) . 2 ? N2 Fe2 N2 92.00(8) 12 2 ? N2 Fe2 N2 88.00(8) 3 2 ? N2 Fe2 N2 88.00(8) 10 11 ? N2 Fe2 N2 92.00(8) . 11 ? N2 Fe2 N2 88.00(8) 12 11 ? N2 Fe2 N2 92.00(8) 3 11 ? N2 Fe2 N2 180.00(14) 2 11 ? N3 Fe1 N3 180.00(9) 2 11_556 ? N3 Fe1 N3 91.03(8) 2 3 ? N3 Fe1 N3 88.97(8) 11_556 3 ? N3 Fe1 N3 91.03(8) 2 . ? N3 Fe1 N3 88.97(8) 11_556 . ? N3 Fe1 N3 91.03(8) 3 . ? N3 Fe1 N3 88.97(8) 2 10_556 ? N3 Fe1 N3 91.03(8) 11_556 10_556 ? N3 Fe1 N3 88.97(8) 3 10_556 ? N3 Fe1 N3 180.00(9) . 10_556 ? N3 Fe1 N3 88.97(8) 2 12_556 ? N3 Fe1 N3 91.03(8) 11_556 12_556 ? N3 Fe1 N3 180.00(9) 3 12_556 ? N3 Fe1 N3 88.97(8) . 12_556 ? N3 Fe1 N3 91.03(8) 10_556 12_556 ? N3 N4 C1 103.8(2) . . ? N2 N3 N4 110.61(19) . . ? N2 N3 Fe1 127.89(16) . . ? N4 N3 Fe1 121.50(16) . . ? N3 N2 N1 108.5(2) . . ? N3 N2 Fe2 123.31(15) . . ? N1 N2 Fe2 128.21(17) . . ? C1 N1 N2 105.3(2) . . ? C1 N1 H1A 127.3 . . ? N2 N1 H1A 127.3 . . ? N1 C1 N4 111.8(2) . . ? N1 C1 C2 127.6(3) . . ? N4 C1 C2 120.6(3) . . ? C4' C2 C3' 118.6(5) . . ? C3 C2 C4 120.2(5) . . ? C4' C2 C1 119.4(4) . . ? C3' C2 C1 122.0(4) . . ? C3 C2 C1 118.9(4) . . ? C4 C2 C1 120.9(4) . . ? C2 C3 C4 121.3(7) . 16 ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.4 16 . ? C4' C3 H3 124.6 . . ? C2 C4 C3 118.6(7) . 16 ? C2 C4 H4 120.4 . . ? C3 C4 H4 121.1 16 . ? C3' C4 H4 122.6 . . ? C2 C3' C4' 119.9(7) . 16 ? C2 C3' H3' 119.8 . . ? C4' C3' H3' 120.3 16 . ? C4 C3' H3' 121.2 . . ? C2 C4' C3' 121.5(7) . 16 ? C2 C4' H4' 119.1 . . ? C3' C4' H4' 119.4 16 . ? C3 C4' H4' 123.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.418 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.087 #===============================END data_complex_3 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 856430' #TrackingRef '- complex_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H7 Fe N12' _chemical_formula_sum 'C12 H7 Fe N12' _chemical_formula_weight 375.15 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Cmmm _symmetry_space_group_name_Hall -C22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x, y, -z' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z' 'x, -y, z' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' _cell_length_a 7.2772(7) _cell_length_b 25.796(3) _cell_length_c 12.2464(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2298.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2210 _cell_measurement_theta_min 3.159 _cell_measurement_theta_max 27.082 _exptl_crystal_description polyhedron _exptl_crystal_colour black _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.084 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.673 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.858 _exptl_absorpt_correction_T_max 0.898 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart Apex 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 5388 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1164 _reflns_number_gt 1043 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.0756P)^2^+10.3524P] 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 1164 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1499 _refine_ls_wR_factor_gt 0.1470 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.073 0.000 -0.004 547 155 ' ' 2 -0.072 0.500 -0.004 547 155 ' ' _platon_squeeze_details ; ; 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 0.2500 0.2500 0.5000 0.0075(3) Uani 1 4 d S . . N4 N 0.0920(4) 0.21899(9) 0.3871(2) 0.0096(6) Uani 1 1 d . . . N3 N 0.1512(4) 0.20121(11) 0.2909(2) 0.0138(6) Uani 1 1 d . . . N2 N 0.0920(5) 0.31119(14) 0.5000 0.0099(8) Uani 1 2 d S . . N1 N 0.1509(5) 0.35988(14) 0.5000 0.0148(9) Uani 1 2 d S . . H1A H 0.2681 0.3711 0.5000 0.018 Uiso 0.50 2 d SPR . . C4 C 0.0000 0.19187(18) 0.2338(4) 0.0144(10) Uani 1 2 d S . . C5 C 0.0000 0.1817(2) 0.1136(4) 0.0182(11) Uani 1 2 d S . . C6 C 0.1603(6) 0.1801(2) 0.0567(3) 0.0483(14) Uani 1 1 d . . . H6A H 0.2737 0.1858 0.0950 0.058 Uiso 1 1 d R . . C1 C 0.0000 0.3884(3) 0.5000 0.0159(15) Uani 1 4 d S . . C2 C 0.0000 0.4464(3) 0.5000 0.0197(16) Uani 1 4 d S . . C3 C 0.1155(12) 0.4729(3) 0.4309(8) 0.034(2) Uani 0.50 1 d P . . H3A H 0.1942 0.4533 0.3834 0.040 Uiso 0.50 1 d 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 0.0072(5) 0.0089(5) 0.0064(5) 0.000 0.000 -0.0002(4) N4 0.0107(13) 0.0105(13) 0.0075(12) 0.0012(11) 0.0027(11) 0.0011(11) N3 0.0121(14) 0.0181(14) 0.0111(13) -0.0045(11) 0.0020(11) 0.0026(11) N2 0.0113(18) 0.0090(19) 0.0093(18) 0.000 0.000 -0.0021(16) N1 0.0081(19) 0.0078(19) 0.028(2) 0.000 0.000 -0.0022(16) C4 0.017(2) 0.017(2) 0.009(2) -0.0006(19) 0.000 0.000 C5 0.026(3) 0.022(3) 0.006(2) 0.000(2) 0.000 0.000 C6 0.020(2) 0.110(5) 0.016(2) -0.003(2) -0.0054(18) 0.017(3) C1 0.017(4) 0.013(3) 0.018(3) 0.000 0.000 0.000 C2 0.016(4) 0.009(3) 0.034(4) 0.000 0.000 0.000 C3 0.035(5) 0.013(4) 0.052(5) -0.003(3) 0.016(4) 0.001(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 N2 1.953(4) . ? Fe1 N2 1.953(4) 13_556 ? Fe1 N4 1.968(3) 13_556 ? Fe1 N4 1.968(3) . ? Fe1 N4 1.968(3) 6 ? Fe1 N4 1.968(3) 10_556 ? N4 N3 1.336(4) . ? N4 N4 1.339(5) 12 ? N3 C4 1.326(4) . ? N2 N1 1.327(5) . ? N2 N2 1.339(8) 3_556 ? N1 C1 1.322(6) . ? N1 H1A 0.9000 . ? C4 N3 1.326(4) 12 ? C4 C5 1.495(7) . ? C5 C6 1.359(5) 12 ? C5 C6 1.359(5) . ? C6 C6 1.389(8) 10 ? C6 H6A 0.9600 . ? C1 N1 1.322(6) 3_556 ? C1 C2 1.494(9) . ? C2 C3 1.375(9) 10_556 ? C2 C3 1.375(9) 3_556 ? C2 C3 1.375(9) 12 ? C2 C3 1.375(9) . ? C3 C3 1.400(15) 11_565 ? C3 H3A 0.9598 . ? 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 N2 Fe1 N2 180.000(1) . 13_556 ? N2 Fe1 N4 90.88(11) . 13_556 ? N2 Fe1 N4 89.12(11) 13_556 13_556 ? N2 Fe1 N4 89.12(11) . . ? N2 Fe1 N4 90.88(11) 13_556 . ? N4 Fe1 N4 180.00(13) 13_556 . ? N2 Fe1 N4 90.88(11) . 6 ? N2 Fe1 N4 89.12(11) 13_556 6 ? N4 Fe1 N4 89.26(15) 13_556 6 ? N4 Fe1 N4 90.74(15) . 6 ? N2 Fe1 N4 89.12(11) . 10_556 ? N2 Fe1 N4 90.88(11) 13_556 10_556 ? N4 Fe1 N4 90.74(15) 13_556 10_556 ? N4 Fe1 N4 89.26(15) . 10_556 ? N4 Fe1 N4 180.00(13) 6 10_556 ? N3 N4 N4 108.81(16) . 12 ? N3 N4 Fe1 124.8(2) . . ? N4 N4 Fe1 125.75(7) 12 . ? C4 N3 N4 105.1(3) . . ? N1 N2 N2 108.8(2) . 3_556 ? N1 N2 Fe1 125.1(3) . . ? N2 N2 Fe1 126.06(11) 3_556 . ? C1 N1 N2 105.0(4) . . ? C1 N1 H1A 127.4 . . ? N2 N1 H1A 127.6 . . ? N3 C4 N3 112.2(4) . 12 ? N3 C4 C5 123.5(2) . . ? N3 C4 C5 123.5(2) 12 . ? C6 C5 C6 118.2(5) 12 . ? C6 C5 C4 120.7(3) 12 . ? C6 C5 C4 120.7(3) . . ? C5 C6 C6 120.8(2) . 10 ? C5 C6 H6A 118.9 . . ? C6 C6 H6A 119.2 10 . ? N1 C1 N1 112.3(6) . 3_556 ? N1 C1 C2 123.8(3) . . ? N1 C1 C2 123.8(3) 3_556 . ? C3 C2 C3 120.4(8) 10_556 12 ? C3 C2 C3 120.4(8) 3_556 . ? C3 C2 C1 119.8(4) 10_556 . ? C3 C2 C1 119.8(4) 3_556 . ? C3 C2 C1 119.8(4) 12 . ? C3 C2 C1 119.8(4) . . ? C2 C3 C3 119.8(4) . 11_565 ? C2 C3 H3A 118.4 . . ? C3 C3 H3A 121.8 11_565 . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.868 _refine_diff_density_min -0.585 _refine_diff_density_rms 0.107 #===============================END data_complex_3a #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 856431' #TrackingRef '- complex_3'.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H7 Fe N12' _chemical_formula_sum 'C12 H7 Fe N12' _chemical_formula_weight 375.15 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Cmmm _symmetry_space_group_name_Hall -C22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x, y, -z' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z' 'x, -y, z' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' _cell_length_a 7.2589(5) _cell_length_b 25.7620(16) _cell_length_c 12.2049(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2282.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1092 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 29.493 _exptl_crystal_description polyhedron _exptl_crystal_colour black _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.092 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.678 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.885 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 Smart Apex 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 4080 _diffrn_reflns_av_R_equivalents 0.0658 _diffrn_reflns_av_sigmaI/netI 0.0827 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1445 _reflns_number_gt 1025 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.0755P)^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 1445 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1345 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.046 0.000 -0.011 532 182 ' ' 2 -0.086 0.500 0.442 532 182 ' ' _platon_squeeze_details ; ; 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 0.2500 0.2500 0.0000 0.0078(3) Uani 1 4 d S . . C1 C 0.0000 0.3892(2) 0.0000 0.0111(12) Uani 1 4 d S . . C2 C 0.0000 0.4461(2) 0.0000 0.0158(13) Uani 1 4 d S . . C3 C 0.1169(8) 0.4726(2) 0.0706(6) 0.0174(13) Uani 0.50 1 d P . . H3A H 0.2064 0.4574 0.1248 0.021 Uiso 0.50 1 d PR . . C4 C 0.0000 0.19191(14) 0.2675(3) 0.0096(8) Uani 1 2 d S . . C5 C 0.0000 0.18095(15) 0.3844(3) 0.0129(9) Uani 1 2 d S . . C6 C 0.1618(5) 0.17922(17) 0.4438(3) 0.0395(10) Uani 1 1 d . . . H6A H 0.3004 0.1841 0.4184 0.047 Uiso 1 1 d R . . N1 N 0.1533(5) 0.36027(12) 0.0000 0.0122(8) Uani 1 2 d S . . H1A H 0.2709 0.3713 0.0000 0.015 Uiso 0.50 2 d SPR . . N4 N 0.0922(3) 0.21883(8) 0.11257(19) 0.0090(5) Uani 1 1 d . . . N3 N 0.1522(3) 0.20110(9) 0.2085(2) 0.0112(5) Uani 1 1 d . . . N2 N 0.0916(4) 0.31105(11) 0.0000 0.0098(7) Uani 1 2 d S . . 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 0.0101(4) 0.0082(4) 0.0052(4) 0.000 0.000 -0.0001(4) C1 0.006(3) 0.010(3) 0.017(3) 0.000 0.000 0.000 C2 0.016(3) 0.010(3) 0.021(4) 0.000 0.000 0.000 C3 0.014(3) 0.013(3) 0.025(3) 0.002(3) -0.006(3) 0.000(2) C4 0.011(2) 0.0090(19) 0.009(2) 0.0002(15) 0.000 0.000 C5 0.018(2) 0.0133(19) 0.008(2) -0.0035(16) 0.000 0.000 C6 0.0121(18) 0.095(3) 0.0115(19) 0.002(2) -0.0036(14) 0.011(2) N1 0.0119(18) 0.0064(16) 0.018(2) 0.000 0.000 -0.0026(14) N4 0.0096(11) 0.0094(10) 0.0081(12) -0.0002(9) 0.0005(10) 0.0013(9) N3 0.0152(13) 0.0141(12) 0.0044(12) 0.0028(9) -0.0006(11) 0.0000(10) N2 0.0089(16) 0.0109(16) 0.0096(18) 0.000 0.000 -0.0028(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N2 1.948(3) 13 ? Fe1 N2 1.948(3) . ? Fe1 N4 1.961(2) 10 ? Fe1 N4 1.961(2) 6 ? Fe1 N4 1.961(2) . ? Fe1 N4 1.961(2) 13 ? C1 N1 1.339(4) 3 ? C1 N1 1.339(4) . ? C1 C2 1.465(8) . ? C2 C3 1.389(7) . ? C2 C3 1.389(7) 3 ? C2 C3 1.389(7) 12 ? C2 C3 1.389(7) 10 ? C3 C3 1.413(11) 11_565 ? C3 H3A 1.0073 . ? C4 N3 1.340(3) . ? C4 N3 1.340(3) 12 ? C4 C5 1.455(6) . ? C5 C6 1.381(4) . ? C5 C6 1.381(4) 12 ? C6 C6 1.371(7) 10_556 ? C6 H6A 1.0601 . ? N1 N2 1.345(4) . ? N1 H1A 0.9001 . ? N4 N3 1.330(3) . ? N4 N4 1.338(4) 12 ? N2 N2 1.329(6) 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 N2 Fe1 N2 180.0 13 . ? N2 Fe1 N4 90.82(9) 13 10 ? N2 Fe1 N4 89.18(9) . 10 ? N2 Fe1 N4 89.18(9) 13 6 ? N2 Fe1 N4 90.82(9) . 6 ? N4 Fe1 N4 180.00(11) 10 6 ? N2 Fe1 N4 90.82(9) 13 . ? N2 Fe1 N4 89.18(9) . . ? N4 Fe1 N4 88.96(13) 10 . ? N4 Fe1 N4 91.04(13) 6 . ? N2 Fe1 N4 89.18(9) 13 13 ? N2 Fe1 N4 90.82(9) . 13 ? N4 Fe1 N4 91.04(13) 10 13 ? N4 Fe1 N4 88.96(13) 6 13 ? N4 Fe1 N4 180.00(11) . 13 ? N1 C1 N1 112.4(4) 3 . ? N1 C1 C2 123.8(2) 3 . ? N1 C1 C2 123.8(2) . . ? C3 C2 C3 121.0(6) . 3 ? C3 C2 C3 121.0(6) 12 10 ? C3 C2 C1 119.5(3) . . ? C3 C2 C1 119.5(3) 3 . ? C3 C2 C1 119.5(3) 12 . ? C3 C2 C1 119.5(3) 10 . ? C2 C3 C3 119.5(3) . 11_565 ? C2 C3 H3A 127.6 . . ? C3 C3 H3A 112.9 11_565 . ? N3 C4 N3 111.1(3) . 12 ? N3 C4 C5 124.14(17) . . ? N3 C4 C5 124.14(17) 12 . ? C6 C5 C6 116.5(4) . 12 ? C6 C5 C4 121.4(2) . . ? C6 C5 C4 121.4(2) 12 . ? C6 C6 C5 121.7(2) 10_556 . ? C6 C6 H6A 107.0 10_556 . ? C5 C6 H6A 130.5 . . ? C1 N1 N2 104.3(3) . . ? C1 N1 H1A 127.7 . . ? N2 N1 H1A 127.9 . . ? N3 N4 N4 109.13(14) . 12 ? N3 N4 Fe1 124.46(18) . . ? N4 N4 Fe1 125.75(7) 12 . ? N4 N3 C4 105.3(2) . . ? N2 N2 N1 109.5(2) 3 . ? N2 N2 Fe1 126.18(9) 3 . ? N1 N2 Fe1 124.4(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.654 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.102 #End of Crystallographic Information File