Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Jiabi Chen' 'Jie Sun' 'Nu Xiao' 'Qiang Xu' _publ_contact_author_name 'Jiabi Chen' _publ_contact_author_address ; State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 CHINA ; _publ_contact_author_email CHENJB@MAIL.SIOC.AC.CN _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Unusual reactions of [{u0(phthalazine-N2: N3)}Fe2(u-CO)(CO)6] with organolithium reagents. A novel coordination mode of 1,2-diazane diiron carbonyl compounds ; data_cd22105 _database_code_depnum_ccdc_archive 'CCDC 225626' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H14 Fe2 N2 O7' _chemical_formula_weight 530.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.786(3) _cell_length_b 9.7314(18) _cell_length_c 17.518(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.790(4) _cell_angle_gamma 90.00 _cell_volume 2211.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1714 _cell_measurement_theta_min 4.861 _cell_measurement_theta_max 38.724 _exptl_crystal_description ? _exptl_crystal_colour red _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 1.358 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.7690 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 '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 13295 _diffrn_reflns_av_R_equivalents 0.0754 _diffrn_reflns_av_sigmaI/netI 0.1134 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 28.30 _reflns_number_total 5192 _reflns_number_gt 2689 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0199P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5192 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1028 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.0790 _refine_ls_wR_factor_gt 0.0684 _refine_ls_goodness_of_fit_ref 0.766 _refine_ls_restrained_S_all 0.766 _refine_ls_shift/su_max 0.111 _refine_ls_shift/su_mean 0.002 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 0.26435(4) -0.07752(5) 0.21491(3) 0.04641(16) Uani 1 1 d . . . Fe2 Fe 0.24300(4) 0.12389(5) 0.11625(3) 0.04210(15) Uani 1 1 d . . . O1 O 0.2040(2) -0.2235(3) 0.33711(16) 0.0790(9) Uani 1 1 d . . . O2 O 0.4753(2) -0.0186(3) 0.32748(16) 0.0767(9) Uani 1 1 d . . . O3 O 0.3252(3) -0.3128(3) 0.1392(2) 0.1071(12) Uani 1 1 d . . . O4 O 0.06264(19) -0.1521(2) 0.08671(14) 0.0678(8) Uani 1 1 d . . . O5 O 0.4653(2) 0.1650(3) 0.17293(17) 0.0758(9) Uani 1 1 d . . . O6 O 0.2271(2) -0.0010(3) -0.03976(16) 0.0809(9) Uani 1 1 d . . . O7 O 0.2095(2) 0.4112(3) 0.06211(15) 0.0676(8) Uani 1 1 d . . . N1 N 0.19996(18) 0.1019(2) 0.20656(14) 0.0384(7) Uani 1 1 d . . . N2 N 0.1154(2) 0.0661(3) 0.13492(15) 0.0416(7) Uani 1 1 d . . . C1 C 0.2272(3) -0.1663(4) 0.2889(2) 0.0562(10) Uani 1 1 d . . . C2 C 0.3942(3) -0.0377(4) 0.2842(2) 0.0547(10) Uani 1 1 d . . . C3 C 0.3048(3) -0.2195(4) 0.1711(3) 0.0683(12) Uani 1 1 d . . . C4 C 0.1291(3) -0.0815(4) 0.1324(2) 0.0485(9) Uani 1 1 d . . . C5 C 0.0161(3) 0.1386(4) 0.1168(2) 0.0502(10) Uani 1 1 d . . . C6 C 0.0328(2) 0.2849(4) 0.1405(2) 0.0398(8) Uani 1 1 d . . . C7 C -0.0229(3) 0.3886(4) 0.0925(2) 0.0511(10) Uani 1 1 d . . . C8 C -0.0069(3) 0.5223(4) 0.1160(2) 0.0552(11) Uani 1 1 d . . . C9 C 0.0652(3) 0.5545(4) 0.1904(2) 0.0576(11) Uani 1 1 d . . . C10 C 0.1227(3) 0.4513(4) 0.2391(2) 0.0482(10) Uani 1 1 d . . . C11 C 0.1092(2) 0.3165(4) 0.21483(18) 0.0390(8) Uani 1 1 d . . . C12 C 0.1722(3) 0.1981(4) 0.26263(19) 0.0393(9) Uani 1 1 d . . . C13 C 0.2711(2) 0.2294(3) 0.32990(19) 0.0383(8) Uani 1 1 d . . . C14 C 0.3457(3) 0.3154(4) 0.3201(2) 0.0481(10) Uani 1 1 d . . . C15 C 0.4396(3) 0.3309(4) 0.3807(2) 0.0559(11) Uani 1 1 d . . . C16 C 0.4634(3) 0.2618(4) 0.4531(2) 0.0592(11) Uani 1 1 d . . . C17 C 0.3890(3) 0.1768(5) 0.4630(2) 0.0568(11) Uani 1 1 d . . . C18 C 0.2944(3) 0.1604(4) 0.4031(2) 0.0461(9) Uani 1 1 d . . . C19 C 0.5672(3) 0.2756(5) 0.5182(2) 0.0907(15) Uani 1 1 d . . . H14 H 0.5762 0.3682 0.5382 0.136 Uiso 1 1 calc R . . H12 H 0.6202 0.2536 0.4962 0.136 Uiso 1 1 calc R . . H13 H 0.5713 0.2136 0.5619 0.136 Uiso 1 1 calc R . . C20 C 0.3776(3) 0.1467(3) 0.1507(2) 0.0516(10) Uani 1 1 d . . . C21 C 0.2357(3) 0.0482(4) 0.0211(2) 0.0531(10) Uani 1 1 d . . . C22 C 0.2173(3) 0.2993(4) 0.0829(2) 0.0474(9) Uani 1 1 d . . . H1 H -0.018(2) 0.125(3) 0.0634(18) 0.050(10) Uiso 1 1 d . . . H2 H -0.021(2) 0.093(3) 0.1433(18) 0.044(10) Uiso 1 1 d . . . H3 H -0.073(2) 0.371(3) 0.0464(17) 0.039(9) Uiso 1 1 d . . . H4 H -0.044(2) 0.595(3) 0.0813(18) 0.053(10) Uiso 1 1 d . . . H5 H 0.078(2) 0.653(3) 0.206(2) 0.075(13) Uiso 1 1 d . . . H6 H 0.171(2) 0.475(3) 0.2868(17) 0.043(10) Uiso 1 1 d . . . H7 H 0.1321(19) 0.143(2) 0.2874(15) 0.025(8) Uiso 1 1 d . . . H8 H 0.334(2) 0.358(3) 0.2724(17) 0.038(9) Uiso 1 1 d . . . H9 H 0.487(2) 0.383(3) 0.3700(17) 0.041(10) Uiso 1 1 d . . . H10 H 0.401(2) 0.128(3) 0.5060(17) 0.044(10) Uiso 1 1 d . . . H11 H 0.2466(18) 0.098(2) 0.4103(15) 0.023(8) Uiso 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 0.0522(3) 0.0439(3) 0.0386(3) 0.0014(2) 0.0094(3) -0.0027(3) Fe2 0.0471(3) 0.0460(3) 0.0329(3) -0.0013(2) 0.0132(2) -0.0031(2) O1 0.077(2) 0.097(2) 0.0588(19) 0.0218(17) 0.0165(17) -0.0116(16) O2 0.0577(19) 0.077(2) 0.078(2) 0.0050(16) -0.0002(16) -0.0043(16) O3 0.118(3) 0.079(2) 0.134(3) -0.038(2) 0.054(2) -0.001(2) O4 0.080(2) 0.0542(17) 0.0502(16) -0.0030(13) -0.0035(14) -0.0205(14) O5 0.0518(18) 0.092(2) 0.083(2) 0.0055(17) 0.0226(17) -0.0109(17) O6 0.088(2) 0.101(2) 0.0566(19) -0.0304(17) 0.0288(17) -0.0079(17) O7 0.085(2) 0.0556(18) 0.0710(19) 0.0139(15) 0.0387(16) 0.0063(16) N1 0.0377(16) 0.0463(18) 0.0249(14) -0.0009(12) 0.0027(13) -0.0050(13) N2 0.0440(18) 0.0468(18) 0.0282(15) -0.0027(13) 0.0047(13) -0.0075(14) C1 0.053(3) 0.059(3) 0.044(2) 0.000(2) 0.000(2) -0.004(2) C2 0.059(3) 0.048(2) 0.052(3) 0.0093(19) 0.013(2) 0.004(2) C3 0.066(3) 0.061(3) 0.072(3) -0.002(2) 0.016(2) -0.007(2) C4 0.063(3) 0.045(2) 0.035(2) 0.0018(17) 0.0121(19) -0.0107(19) C5 0.042(3) 0.069(3) 0.034(2) 0.004(2) 0.007(2) -0.007(2) C6 0.034(2) 0.050(2) 0.035(2) 0.0008(17) 0.0120(17) -0.0019(17) C7 0.038(2) 0.072(3) 0.039(2) 0.001(2) 0.0068(19) 0.001(2) C8 0.054(3) 0.061(3) 0.048(3) 0.011(2) 0.014(2) 0.015(2) C9 0.062(3) 0.053(3) 0.055(3) -0.005(2) 0.016(2) 0.006(2) C10 0.048(3) 0.058(3) 0.037(2) -0.005(2) 0.012(2) 0.005(2) C11 0.037(2) 0.055(2) 0.0276(19) 0.0014(17) 0.0138(16) -0.0009(17) C12 0.038(2) 0.053(2) 0.0278(19) 0.0022(17) 0.0116(17) -0.0073(18) C13 0.037(2) 0.047(2) 0.0311(19) -0.0061(16) 0.0112(17) -0.0023(17) C14 0.052(3) 0.055(3) 0.037(2) 0.003(2) 0.015(2) -0.008(2) C15 0.043(3) 0.071(3) 0.053(3) -0.007(2) 0.016(2) -0.020(2) C16 0.046(3) 0.086(3) 0.041(2) -0.007(2) 0.008(2) -0.011(2) C17 0.054(3) 0.084(3) 0.028(2) 0.006(2) 0.008(2) -0.001(2) C18 0.047(2) 0.059(3) 0.031(2) -0.0002(18) 0.0122(19) -0.009(2) C19 0.054(3) 0.147(4) 0.054(3) -0.006(3) -0.005(2) -0.020(3) C20 0.065(3) 0.048(2) 0.045(2) 0.0028(18) 0.024(2) -0.003(2) C21 0.051(2) 0.055(2) 0.052(3) -0.004(2) 0.016(2) -0.0020(19) C22 0.049(2) 0.060(3) 0.038(2) -0.0026(19) 0.0197(19) -0.004(2) _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 C3 1.760(5) . ? Fe1 C1 1.772(4) . ? Fe1 C2 1.832(4) . ? Fe1 C4 1.935(4) . ? Fe1 N1 1.941(2) . ? Fe1 Fe2 2.5633(7) . ? Fe2 C20 1.760(4) . ? Fe2 C21 1.793(4) . ? Fe2 C22 1.800(4) . ? Fe2 N1 1.881(2) . ? Fe2 N2 1.976(3) . ? O1 C1 1.143(4) . ? O2 C2 1.134(4) . ? O3 C3 1.150(4) . ? O4 C4 1.206(3) . ? O5 C20 1.152(4) . ? O6 C21 1.138(4) . ? O7 C22 1.142(4) . ? N1 N2 1.437(3) . ? N1 C12 1.498(4) . ? N2 C4 1.452(4) . ? N2 C5 1.476(4) . ? C5 C6 1.478(5) . ? C5 H1 0.90(3) . ? C5 H2 0.91(3) . ? C6 C7 1.370(4) . ? C6 C11 1.404(4) . ? C7 C8 1.360(5) . ? C7 H3 0.88(3) . ? C8 C9 1.382(5) . ? C8 H4 0.96(3) . ? C9 C10 1.381(5) . ? C9 H5 0.99(3) . ? C10 C11 1.372(4) . ? C10 H6 0.91(3) . ? C11 C12 1.513(4) . ? C12 C13 1.501(4) . ? C12 H7 0.97(2) . ? C13 C14 1.381(4) . ? C13 C18 1.386(4) . ? C14 C15 1.376(5) . ? C14 H8 0.89(3) . ? C15 C16 1.373(5) . ? C15 H9 0.90(3) . ? C16 C17 1.374(5) . ? C16 C19 1.504(4) . ? C17 C18 1.379(5) . ? C17 H10 0.86(3) . ? C18 H11 0.93(2) . ? C19 H14 0.9600 . ? C19 H12 0.9600 . ? C19 H13 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 C3 Fe1 C1 98.57(18) . . ? C3 Fe1 C2 94.12(17) . . ? C1 Fe1 C2 94.48(16) . . ? C3 Fe1 C4 91.49(16) . . ? C1 Fe1 C4 95.31(15) . . ? C2 Fe1 C4 167.87(15) . . ? C3 Fe1 N1 151.33(15) . . ? C1 Fe1 N1 104.78(14) . . ? C2 Fe1 N1 100.32(13) . . ? C4 Fe1 N1 70.21(12) . . ? C3 Fe1 Fe2 106.71(14) . . ? C1 Fe1 Fe2 150.51(12) . . ? C2 Fe1 Fe2 98.54(11) . . ? C4 Fe1 Fe2 69.51(10) . . ? N1 Fe1 Fe2 46.88(7) . . ? C20 Fe2 C21 95.26(16) . . ? C20 Fe2 C22 93.46(15) . . ? C21 Fe2 C22 98.34(16) . . ? C20 Fe2 N1 108.77(13) . . ? C21 Fe2 N1 143.18(14) . . ? C22 Fe2 N1 107.32(13) . . ? C20 Fe2 N2 150.80(13) . . ? C21 Fe2 N2 105.31(13) . . ? C22 Fe2 N2 103.59(13) . . ? N1 Fe2 N2 43.65(9) . . ? C20 Fe2 Fe1 89.89(11) . . ? C21 Fe2 Fe1 105.66(12) . . ? C22 Fe2 Fe1 155.36(11) . . ? N1 Fe2 Fe1 48.89(8) . . ? N2 Fe2 Fe1 64.94(8) . . ? N2 N1 C12 114.3(2) . . ? N2 N1 Fe2 71.72(14) . . ? C12 N1 Fe2 134.7(2) . . ? N2 N1 Fe1 93.62(17) . . ? C12 N1 Fe1 136.47(19) . . ? Fe2 N1 Fe1 84.22(10) . . ? N1 N2 C4 101.0(2) . . ? N1 N2 C5 119.4(3) . . ? C4 N2 C5 125.9(3) . . ? N1 N2 Fe2 64.63(14) . . ? C4 N2 Fe2 98.3(2) . . ? C5 N2 Fe2 129.9(2) . . ? O1 C1 Fe1 179.4(3) . . ? O2 C2 Fe1 177.2(3) . . ? O3 C3 Fe1 175.8(4) . . ? O4 C4 N2 120.4(3) . . ? O4 C4 Fe1 146.2(3) . . ? N2 C4 Fe1 93.4(2) . . ? N2 C5 C6 110.8(3) . . ? N2 C5 H1 105.8(19) . . ? C6 C5 H1 113.9(19) . . ? N2 C5 H2 107.3(19) . . ? C6 C5 H2 112.6(19) . . ? H1 C5 H2 106(3) . . ? C7 C6 C11 119.7(3) . . ? C7 C6 C5 122.4(3) . . ? C11 C6 C5 117.9(3) . . ? C8 C7 C6 121.4(4) . . ? C8 C7 H3 117.3(19) . . ? C6 C7 H3 121.3(19) . . ? C7 C8 C9 119.5(4) . . ? C7 C8 H4 121.1(18) . . ? C9 C8 H4 119.3(18) . . ? C10 C9 C8 119.8(4) . . ? C10 C9 H5 121(2) . . ? C8 C9 H5 119(2) . . ? C11 C10 C9 121.0(4) . . ? C11 C10 H6 120.4(19) . . ? C9 C10 H6 118.6(19) . . ? C10 C11 C6 118.5(3) . . ? C10 C11 C12 124.3(3) . . ? C6 C11 C12 117.2(3) . . ? N1 C12 C13 106.0(3) . . ? N1 C12 C11 109.9(2) . . ? C13 C12 C11 118.6(3) . . ? N1 C12 H7 105.0(15) . . ? C13 C12 H7 105.3(15) . . ? C11 C12 H7 111.1(15) . . ? C14 C13 C18 117.4(3) . . ? C14 C13 C12 122.8(3) . . ? C18 C13 C12 119.5(3) . . ? C15 C14 C13 121.0(4) . . ? C15 C14 H8 120.1(19) . . ? C13 C14 H8 118.8(19) . . ? C16 C15 C14 121.9(4) . . ? C16 C15 H9 120.4(19) . . ? C14 C15 H9 118(2) . . ? C15 C16 C17 117.1(4) . . ? C15 C16 C19 121.7(4) . . ? C17 C16 C19 121.1(4) . . ? C16 C17 C18 121.8(4) . . ? C16 C17 H10 121(2) . . ? C18 C17 H10 117(2) . . ? C17 C18 C13 120.8(4) . . ? C17 C18 H11 120.1(16) . . ? C13 C18 H11 119.1(16) . . ? C16 C19 H14 109.5 . . ? C16 C19 H12 109.5 . . ? H14 C19 H12 109.5 . . ? C16 C19 H13 109.5 . . ? H14 C19 H13 109.5 . . ? H12 C19 H13 109.5 . . ? O5 C20 Fe2 178.4(3) . . ? O6 C21 Fe2 177.3(3) . . ? O7 C22 Fe2 174.2(3) . . ? 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 C3 Fe1 Fe2 C20 -77.74(17) . . . . ? C1 Fe1 Fe2 C20 134.4(3) . . . . ? C2 Fe1 Fe2 C20 19.20(16) . . . . ? C4 Fe1 Fe2 C20 -162.97(16) . . . . ? N1 Fe1 Fe2 C20 115.38(15) . . . . ? C3 Fe1 Fe2 C21 17.69(18) . . . . ? C1 Fe1 Fe2 C21 -130.2(3) . . . . ? C2 Fe1 Fe2 C21 114.63(16) . . . . ? C4 Fe1 Fe2 C21 -67.54(16) . . . . ? N1 Fe1 Fe2 C21 -149.19(15) . . . . ? C3 Fe1 Fe2 C22 -175.8(3) . . . . ? C1 Fe1 Fe2 C22 36.3(4) . . . . ? C2 Fe1 Fe2 C22 -78.9(3) . . . . ? C4 Fe1 Fe2 C22 98.9(3) . . . . ? N1 Fe1 Fe2 C22 17.3(3) . . . . ? C3 Fe1 Fe2 N1 166.87(16) . . . . ? C1 Fe1 Fe2 N1 19.0(2) . . . . ? C2 Fe1 Fe2 N1 -96.18(15) . . . . ? C4 Fe1 Fe2 N1 81.65(15) . . . . ? C3 Fe1 Fe2 N2 117.57(15) . . . . ? C1 Fe1 Fe2 N2 -30.3(2) . . . . ? C2 Fe1 Fe2 N2 -145.48(14) . . . . ? C4 Fe1 Fe2 N2 32.35(13) . . . . ? N1 Fe1 Fe2 N2 -49.30(12) . . . . ? C20 Fe2 N1 N2 -168.35(18) . . . . ? C21 Fe2 N1 N2 -40.4(3) . . . . ? C22 Fe2 N1 N2 91.70(18) . . . . ? Fe1 Fe2 N1 N2 -95.75(16) . . . . ? C20 Fe2 N1 C12 85.2(3) . . . . ? C21 Fe2 N1 C12 -146.8(3) . . . . ? C22 Fe2 N1 C12 -14.8(3) . . . . ? N2 Fe2 N1 C12 -106.5(3) . . . . ? Fe1 Fe2 N1 C12 157.8(3) . . . . ? C20 Fe2 N1 Fe1 -72.59(14) . . . . ? C21 Fe2 N1 Fe1 55.4(2) . . . . ? C22 Fe2 N1 Fe1 -172.54(12) . . . . ? N2 Fe2 N1 Fe1 95.75(16) . . . . ? C3 Fe1 N1 N2 44.2(4) . . . . ? C1 Fe1 N1 N2 -99.25(18) . . . . ? C2 Fe1 N1 N2 163.27(17) . . . . ? C4 Fe1 N1 N2 -8.86(17) . . . . ? Fe2 Fe1 N1 N2 71.20(14) . . . . ? C3 Fe1 N1 C12 176.0(3) . . . . ? C1 Fe1 N1 C12 32.5(3) . . . . ? C2 Fe1 N1 C12 -65.0(3) . . . . ? C4 Fe1 N1 C12 122.9(3) . . . . ? Fe2 Fe1 N1 C12 -157.0(3) . . . . ? C3 Fe1 N1 Fe2 -27.0(3) . . . . ? C1 Fe1 N1 Fe2 -170.45(12) . . . . ? C2 Fe1 N1 Fe2 92.07(13) . . . . ? C4 Fe1 N1 Fe2 -80.06(12) . . . . ? C12 N1 N2 C4 -134.3(3) . . . . ? Fe2 N1 N2 C4 94.0(2) . . . . ? Fe1 N1 N2 C4 11.3(2) . . . . ? C12 N1 N2 C5 8.4(4) . . . . ? Fe2 N1 N2 C5 -123.2(3) . . . . ? Fe1 N1 N2 C5 154.1(3) . . . . ? C12 N1 N2 Fe2 131.6(2) . . . . ? Fe1 N1 N2 Fe2 -82.70(10) . . . . ? C20 Fe2 N2 N1 23.1(3) . . . . ? C21 Fe2 N2 N1 156.27(17) . . . . ? C22 Fe2 N2 N1 -100.97(17) . . . . ? Fe1 Fe2 N2 N1 55.85(13) . . . . ? C20 Fe2 N2 C4 -75.2(3) . . . . ? C21 Fe2 N2 C4 58.0(2) . . . . ? C22 Fe2 N2 C4 160.7(2) . . . . ? N1 Fe2 N2 C4 -98.3(2) . . . . ? Fe1 Fe2 N2 C4 -42.45(16) . . . . ? C20 Fe2 N2 C5 131.3(3) . . . . ? C21 Fe2 N2 C5 -95.5(3) . . . . ? C22 Fe2 N2 C5 7.2(3) . . . . ? N1 Fe2 N2 C5 108.2(3) . . . . ? Fe1 Fe2 N2 C5 164.0(3) . . . . ? C3 Fe1 C1 O1 84(38) . . . . ? C2 Fe1 C1 O1 -10(38) . . . . ? C4 Fe1 C1 O1 177(100) . . . . ? N1 Fe1 C1 O1 -112(38) . . . . ? Fe2 Fe1 C1 O1 -127(38) . . . . ? C3 Fe1 C2 O2 -38(7) . . . . ? C1 Fe1 C2 O2 61(7) . . . . ? C4 Fe1 C2 O2 -155(7) . . . . ? N1 Fe1 C2 O2 167(7) . . . . ? Fe2 Fe1 C2 O2 -145(7) . . . . ? C1 Fe1 C3 O3 91(6) . . . . ? C2 Fe1 C3 O3 -174(6) . . . . ? C4 Fe1 C3 O3 -4(6) . . . . ? N1 Fe1 C3 O3 -53(6) . . . . ? Fe2 Fe1 C3 O3 -73(6) . . . . ? N1 N2 C4 O4 168.7(3) . . . . ? C5 N2 C4 O4 29.3(5) . . . . ? Fe2 N2 C4 O4 -125.7(3) . . . . ? N1 N2 C4 Fe1 -11.4(2) . . . . ? C5 N2 C4 Fe1 -150.8(3) . . . . ? Fe2 N2 C4 Fe1 54.24(15) . . . . ? C3 Fe1 C4 O4 31.2(5) . . . . ? C1 Fe1 C4 O4 -67.5(5) . . . . ? C2 Fe1 C4 O4 148.8(7) . . . . ? N1 Fe1 C4 O4 -171.3(5) . . . . ? Fe2 Fe1 C4 O4 138.5(5) . . . . ? C3 Fe1 C4 N2 -148.7(2) . . . . ? C1 Fe1 C4 N2 112.6(2) . . . . ? C2 Fe1 C4 N2 -31.1(8) . . . . ? N1 Fe1 C4 N2 8.76(16) . . . . ? Fe2 Fe1 C4 N2 -41.37(15) . . . . ? N1 N2 C5 C6 36.4(4) . . . . ? C4 N2 C5 C6 169.2(3) . . . . ? Fe2 N2 C5 C6 -43.8(4) . . . . ? N2 C5 C6 C7 137.3(3) . . . . ? N2 C5 C6 C11 -42.4(4) . . . . ? C11 C6 C7 C8 -1.0(5) . . . . ? C5 C6 C7 C8 179.3(4) . . . . ? C6 C7 C8 C9 -1.5(6) . . . . ? C7 C8 C9 C10 2.2(6) . . . . ? C8 C9 C10 C11 -0.3(6) . . . . ? C9 C10 C11 C6 -2.2(5) . . . . ? C9 C10 C11 C12 177.1(3) . . . . ? C7 C6 C11 C10 2.8(5) . . . . ? C5 C6 C11 C10 -177.5(3) . . . . ? C7 C6 C11 C12 -176.5(3) . . . . ? C5 C6 C11 C12 3.2(4) . . . . ? N2 N1 C12 C13 -176.4(2) . . . . ? Fe2 N1 C12 C13 -88.5(3) . . . . ? Fe1 N1 C12 C13 58.4(4) . . . . ? N2 N1 C12 C11 -47.1(3) . . . . ? Fe2 N1 C12 C11 40.8(4) . . . . ? Fe1 N1 C12 C11 -172.3(2) . . . . ? C10 C11 C12 N1 -137.3(3) . . . . ? C6 C11 C12 N1 42.0(4) . . . . ? C10 C11 C12 C13 -15.3(5) . . . . ? C6 C11 C12 C13 164.0(3) . . . . ? N1 C12 C13 C14 74.3(4) . . . . ? C11 C12 C13 C14 -49.6(5) . . . . ? N1 C12 C13 C18 -99.5(3) . . . . ? C11 C12 C13 C18 136.6(3) . . . . ? C18 C13 C14 C15 0.4(5) . . . . ? C12 C13 C14 C15 -173.6(3) . . . . ? C13 C14 C15 C16 0.2(6) . . . . ? C14 C15 C16 C17 -0.6(6) . . . . ? C14 C15 C16 C19 178.1(4) . . . . ? C15 C16 C17 C18 0.3(6) . . . . ? C19 C16 C17 C18 -178.4(4) . . . . ? C16 C17 C18 C13 0.3(6) . . . . ? C14 C13 C18 C17 -0.7(5) . . . . ? C12 C13 C18 C17 173.5(3) . . . . ? C21 Fe2 C20 O5 105(12) . . . . ? C22 Fe2 C20 O5 6(12) . . . . ? N1 Fe2 C20 O5 -104(12) . . . . ? N2 Fe2 C20 O5 -120(12) . . . . ? Fe1 Fe2 C20 O5 -150(12) . . . . ? C20 Fe2 C21 O6 172(7) . . . . ? C22 Fe2 C21 O6 -93(7) . . . . ? N1 Fe2 C21 O6 41(8) . . . . ? N2 Fe2 C21 O6 13(7) . . . . ? Fe1 Fe2 C21 O6 81(7) . . . . ? C20 Fe2 C22 O7 16(3) . . . . ? C21 Fe2 C22 O7 -80(3) . . . . ? N1 Fe2 C22 O7 127(3) . . . . ? N2 Fe2 C22 O7 172(3) . . . . ? Fe1 Fe2 C22 O7 114(3) . . . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.417 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.075 data_cd22406 _database_code_depnum_ccdc_archive 'CCDC 278404' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H14 Cl2 Fe2 N2 O8' _chemical_formula_weight 628.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1738(10) _cell_length_b 10.2354(10) _cell_length_c 12.7042(13) _cell_angle_alpha 85.943(2) _cell_angle_beta 86.833(2) _cell_angle_gamma 79.760(2) _cell_volume 1297.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1709 _cell_measurement_theta_min 5.015 _cell_measurement_theta_max 45.202 _exptl_crystal_description ? _exptl_crystal_colour red _exptl_crystal_size_max 0.364 _exptl_crystal_size_mid 0.336 _exptl_crystal_size_min 0.051 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 1.373 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.76847 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _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 '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 7894 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0925 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 28.29 _reflns_number_total 5727 _reflns_number_gt 3297 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1068P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5727 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.1979 _refine_ls_wR_factor_gt 0.1763 _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_restrained_S_all 0.910 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.003 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 0.26922(7) 0.68139(7) 0.35725(6) 0.0410(2) Uani 1 1 d . . . Fe2 Fe 0.16153(7) 0.74931(7) 0.53571(6) 0.0418(2) Uani 1 1 d . . . Cl1 Cl 0.5526(4) 0.7730(5) 0.9144(4) 0.219(2) Uani 1 1 d . . . Cl2 Cl 0.8211(6) 0.7902(5) 0.8578(4) 0.251(3) Uani 1 1 d . . . N1 N 0.0739(4) 0.7461(4) 0.3350(3) 0.0383(10) Uani 1 1 d . . . N2 N 0.0177(4) 0.7752(4) 0.4338(3) 0.0377(9) Uani 1 1 d . . . O1 O 0.2364(5) 0.3972(4) 0.3796(5) 0.0872(16) Uani 1 1 d . . . O2 O 0.3910(4) 0.7375(6) 0.1491(4) 0.0920(18) Uani 1 1 d . . . O3 O 0.5433(4) 0.6116(5) 0.4230(4) 0.0728(13) Uani 1 1 d . . . O4 O 0.2886(4) 0.9540(4) 0.4118(3) 0.0578(11) Uani 1 1 d . . . O5 O 0.4077(5) 0.7307(5) 0.6461(4) 0.0887(16) Uani 1 1 d . . . O6 O 0.0210(5) 0.9297(4) 0.6897(4) 0.0743(13) Uani 1 1 d . . . O7 O 0.0998(5) 0.4880(4) 0.6202(4) 0.0841(15) Uani 1 1 d . . . O8 O 0.2446(5) 0.6381(5) -0.1439(4) 0.0879(15) Uani 1 1 d . . . C1 C 0.2469(5) 0.5061(6) 0.3690(5) 0.0559(15) Uani 1 1 d . . . C2 C 0.3345(6) 0.7203(7) 0.2272(5) 0.0591(16) Uani 1 1 d . . . C3 C 0.4349(6) 0.6378(5) 0.3979(5) 0.0514(14) Uani 1 1 d . . . C4 C 0.2546(5) 0.8511(5) 0.4256(4) 0.0428(12) Uani 1 1 d . . . C5 C -0.1107(5) 0.8172(5) 0.4459(4) 0.0418(12) Uani 1 1 d . . . H1 H -0.1462 0.8329 0.5138 0.050 Uiso 1 1 calc R . . C6 C -0.1979(5) 0.8401(5) 0.3626(4) 0.0428(12) Uani 1 1 d . . . C7 C -0.3356(5) 0.8904(6) 0.3751(5) 0.0565(15) Uani 1 1 d . . . H2 H -0.3739 0.9071 0.4420 0.068 Uiso 1 1 calc R . . C8 C -0.4125(6) 0.9144(7) 0.2894(6) 0.0681(18) Uani 1 1 d . . . H3 H -0.5030 0.9497 0.2979 0.082 Uiso 1 1 calc R . . C9 C -0.3572(6) 0.8866(6) 0.1891(6) 0.0648(17) Uani 1 1 d . . . H4 H -0.4121 0.9006 0.1317 0.078 Uiso 1 1 calc R . . C10 C -0.2217(6) 0.8383(6) 0.1729(5) 0.0603(16) Uani 1 1 d . . . H5 H -0.1851 0.8230 0.1053 0.072 Uiso 1 1 calc R . . C11 C -0.1410(5) 0.8131(5) 0.2608(4) 0.0418(12) Uani 1 1 d . . . C12 C -0.0015(5) 0.7634(5) 0.2513(4) 0.0384(11) Uani 1 1 d . . . C13 C 0.0641(5) 0.7290(5) 0.1483(4) 0.0420(12) Uani 1 1 d . . . C14 C 0.0874(6) 0.8271(6) 0.0712(5) 0.0564(15) Uani 1 1 d . . . H6 H 0.0619 0.9161 0.0858 0.068 Uiso 1 1 calc R . . C15 C 0.1471(6) 0.7957(6) -0.0259(5) 0.0655(17) Uani 1 1 d . . . H7 H 0.1628 0.8624 -0.0762 0.079 Uiso 1 1 calc R . . C16 C 0.1839(6) 0.6617(6) -0.0475(5) 0.0570(15) Uani 1 1 d . . . C17 C 0.1574(6) 0.5640(6) 0.0270(5) 0.0624(17) Uani 1 1 d . . . H8 H 0.1799 0.4749 0.0120 0.075 Uiso 1 1 calc R . . C18 C 0.0979(6) 0.5977(6) 0.1231(5) 0.0549(15) Uani 1 1 d . . . H9 H 0.0798 0.5309 0.1723 0.066 Uiso 1 1 calc R . . C19 C 0.3048(10) 0.5053(8) -0.1616(6) 0.122(4) Uani 1 1 d . . . H10 H 0.3701 0.4741 -0.1098 0.184 Uiso 1 1 calc R . . H11 H 0.3474 0.5019 -0.2309 0.184 Uiso 1 1 calc R . . H12 H 0.2375 0.4499 -0.1562 0.184 Uiso 1 1 calc R . . C20 C 0.3103(7) 0.7349(6) 0.6055(5) 0.0583(15) Uani 1 1 d . . . C21 C 0.0742(6) 0.8632(5) 0.6272(4) 0.0482(14) Uani 1 1 d . . . C22 C 0.1230(6) 0.5883(6) 0.5862(5) 0.0542(14) Uani 1 1 d . . . C23 C 0.6742(15) 0.837(3) 0.8430(13) 0.54(3) Uani 1 1 d . . . H14 H 0.6596 0.8268 0.7695 0.645 Uiso 1 1 calc R . . H13 H 0.6571 0.9317 0.8525 0.645 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0367(4) 0.0386(4) 0.0457(5) -0.0104(3) 0.0025(3) 0.0006(3) Fe2 0.0449(4) 0.0400(4) 0.0405(5) -0.0059(3) 0.0025(3) -0.0076(3) Cl1 0.160(3) 0.277(5) 0.204(5) -0.017(4) -0.042(3) 0.016(3) Cl2 0.340(7) 0.201(4) 0.224(5) 0.000(4) 0.103(5) -0.121(5) N1 0.036(2) 0.034(2) 0.044(3) -0.0085(19) 0.0073(19) -0.0027(17) N2 0.039(2) 0.039(2) 0.036(2) -0.0067(18) 0.0062(18) -0.0077(18) O1 0.095(4) 0.042(3) 0.125(5) -0.015(3) -0.005(3) -0.010(2) O2 0.059(3) 0.170(6) 0.050(3) -0.002(3) 0.009(2) -0.036(3) O3 0.047(2) 0.078(3) 0.091(4) 0.002(3) -0.011(2) -0.003(2) O4 0.060(2) 0.042(2) 0.072(3) -0.011(2) 0.022(2) -0.0159(19) O5 0.069(3) 0.122(5) 0.078(4) -0.012(3) -0.022(3) -0.017(3) O6 0.096(3) 0.062(3) 0.068(3) -0.024(2) 0.024(3) -0.021(2) O7 0.100(4) 0.053(3) 0.101(4) 0.017(3) -0.010(3) -0.025(3) O8 0.114(4) 0.086(3) 0.050(3) -0.005(2) 0.027(3) 0.012(3) C1 0.045(3) 0.053(4) 0.070(4) -0.016(3) -0.004(3) -0.004(3) C2 0.039(3) 0.081(5) 0.059(4) -0.015(3) -0.003(3) -0.010(3) C3 0.048(3) 0.048(3) 0.056(4) -0.010(3) -0.002(3) 0.001(3) C4 0.039(3) 0.043(3) 0.044(3) -0.007(2) 0.002(2) -0.004(2) C5 0.043(3) 0.037(3) 0.047(3) -0.012(2) 0.013(2) -0.012(2) C6 0.035(3) 0.038(3) 0.056(3) -0.013(2) 0.006(2) -0.009(2) C7 0.038(3) 0.062(4) 0.070(4) -0.014(3) 0.010(3) -0.010(3) C8 0.035(3) 0.078(5) 0.090(5) -0.007(4) -0.003(3) -0.005(3) C9 0.039(3) 0.075(4) 0.078(5) 0.001(4) -0.010(3) -0.003(3) C10 0.045(3) 0.068(4) 0.068(4) -0.004(3) 0.001(3) -0.012(3) C11 0.037(3) 0.039(3) 0.051(3) -0.005(2) -0.002(2) -0.010(2) C12 0.039(3) 0.032(3) 0.044(3) -0.005(2) 0.002(2) -0.005(2) C13 0.038(3) 0.046(3) 0.043(3) -0.012(2) 0.001(2) -0.005(2) C14 0.060(4) 0.042(3) 0.061(4) -0.002(3) 0.010(3) 0.004(3) C15 0.066(4) 0.064(4) 0.059(4) 0.007(3) 0.014(3) 0.001(3) C16 0.067(4) 0.059(4) 0.040(3) -0.006(3) 0.002(3) 0.004(3) C17 0.076(4) 0.052(4) 0.055(4) -0.018(3) 0.005(3) 0.004(3) C18 0.067(4) 0.048(3) 0.049(4) -0.004(3) 0.003(3) -0.010(3) C19 0.198(10) 0.082(6) 0.065(5) -0.020(4) 0.043(6) 0.028(6) C20 0.064(4) 0.064(4) 0.049(4) -0.008(3) -0.004(3) -0.014(3) C21 0.062(4) 0.044(3) 0.041(3) -0.004(3) 0.007(3) -0.018(3) C22 0.060(4) 0.050(4) 0.053(4) -0.006(3) -0.005(3) -0.008(3) C23 0.162(13) 0.99(6) 0.227(18) 0.37(3) 0.116(13) 0.34(2) _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 C3 1.762(6) . ? Fe1 C2 1.791(7) . ? Fe1 C1 1.843(6) . ? Fe1 C4 1.975(5) . ? Fe1 N1 2.008(4) . ? Fe1 Fe2 2.5498(10) . ? Fe2 C20 1.775(7) . ? Fe2 C21 1.792(6) . ? Fe2 C22 1.826(6) . ? Fe2 N2 1.978(4) . ? Fe2 C4 1.984(6) . ? Cl1 C23 1.69(2) . ? Cl2 C23 1.503(14) . ? N1 C12 1.329(6) . ? N1 N2 1.380(5) . ? N2 C5 1.304(6) . ? O1 C1 1.136(7) . ? O2 C2 1.138(7) . ? O3 C3 1.145(6) . ? O4 C4 1.165(6) . ? O5 C20 1.135(7) . ? O6 C21 1.133(6) . ? O7 C22 1.144(7) . ? O8 C16 1.358(7) . ? O8 C19 1.416(8) . ? C5 C6 1.400(7) . ? C5 H1 0.9300 . ? C6 C7 1.408(7) . ? C6 C11 1.412(7) . ? C7 C8 1.358(9) . ? C7 H2 0.9300 . ? C8 C9 1.392(9) . ? C8 H3 0.9300 . ? C9 C10 1.388(8) . ? C9 H4 0.9300 . ? C10 C11 1.404(8) . ? C10 H5 0.9300 . ? C11 C12 1.422(7) . ? C12 C13 1.472(7) . ? C13 C18 1.382(7) . ? C13 C14 1.394(8) . ? C14 C15 1.378(8) . ? C14 H6 0.9300 . ? C15 C16 1.399(8) . ? C15 H7 0.9300 . ? C16 C17 1.379(9) . ? C17 C18 1.371(8) . ? C17 H8 0.9300 . ? C18 H9 0.9300 . ? C19 H10 0.9600 . ? C19 H11 0.9600 . ? C19 H12 0.9600 . ? C23 H14 0.9700 . ? C23 H13 0.9700 . ? 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 C3 Fe1 C2 88.4(3) . . ? C3 Fe1 C1 91.6(3) . . ? C2 Fe1 C1 109.4(3) . . ? C3 Fe1 C4 88.9(2) . . ? C2 Fe1 C4 102.7(3) . . ? C1 Fe1 C4 147.8(3) . . ? C3 Fe1 N1 170.0(2) . . ? C2 Fe1 N1 99.0(2) . . ? C1 Fe1 N1 92.2(2) . . ? C4 Fe1 N1 83.02(18) . . ? C3 Fe1 Fe2 97.13(19) . . ? C2 Fe1 Fe2 151.8(2) . . ? C1 Fe1 Fe2 98.05(19) . . ? C4 Fe1 Fe2 50.06(16) . . ? N1 Fe1 Fe2 73.18(12) . . ? C20 Fe2 C21 90.6(3) . . ? C20 Fe2 C22 95.1(3) . . ? C21 Fe2 C22 104.0(2) . . ? C20 Fe2 N2 168.8(2) . . ? C21 Fe2 N2 95.8(2) . . ? C22 Fe2 N2 92.3(2) . . ? C20 Fe2 C4 85.1(2) . . ? C21 Fe2 C4 108.4(2) . . ? C22 Fe2 C4 147.7(2) . . ? N2 Fe2 C4 84.17(19) . . ? C20 Fe2 Fe1 97.9(2) . . ? C21 Fe2 Fe1 155.15(18) . . ? C22 Fe2 Fe1 98.50(18) . . ? N2 Fe2 Fe1 72.61(11) . . ? C4 Fe2 Fe1 49.75(15) . . ? C12 N1 N2 120.4(4) . . ? C12 N1 Fe1 134.3(3) . . ? N2 N1 Fe1 105.3(3) . . ? C5 N2 N1 120.1(4) . . ? C5 N2 Fe2 131.1(4) . . ? N1 N2 Fe2 108.7(3) . . ? C16 O8 C19 117.2(5) . . ? O1 C1 Fe1 177.2(6) . . ? O2 C2 Fe1 171.4(6) . . ? O3 C3 Fe1 178.6(6) . . ? O4 C4 Fe1 140.1(4) . . ? O4 C4 Fe2 139.5(4) . . ? Fe1 C4 Fe2 80.2(2) . . ? N2 C5 C6 123.7(5) . . ? N2 C5 H1 118.1 . . ? C6 C5 H1 118.1 . . ? C5 C6 C7 123.7(5) . . ? C5 C6 C11 116.7(4) . . ? C7 C6 C11 119.6(5) . . ? C8 C7 C6 120.1(6) . . ? C8 C7 H2 120.0 . . ? C6 C7 H2 120.0 . . ? C7 C8 C9 120.6(6) . . ? C7 C8 H3 119.7 . . ? C9 C8 H3 119.7 . . ? C10 C9 C8 121.3(6) . . ? C10 C9 H4 119.4 . . ? C8 C9 H4 119.4 . . ? C9 C10 C11 118.7(6) . . ? C9 C10 H5 120.7 . . ? C11 C10 H5 120.7 . . ? C10 C11 C6 119.8(5) . . ? C10 C11 C12 122.3(5) . . ? C6 C11 C12 117.9(5) . . ? N1 C12 C11 121.2(5) . . ? N1 C12 C13 117.8(4) . . ? C11 C12 C13 121.0(5) . . ? C18 C13 C14 117.9(5) . . ? C18 C13 C12 120.6(5) . . ? C14 C13 C12 121.4(5) . . ? C15 C14 C13 121.7(5) . . ? C15 C14 H6 119.2 . . ? C13 C14 H6 119.2 . . ? C14 C15 C16 118.8(6) . . ? C14 C15 H7 120.6 . . ? C16 C15 H7 120.6 . . ? O8 C16 C17 124.5(5) . . ? O8 C16 C15 115.6(6) . . ? C17 C16 C15 119.9(5) . . ? C18 C17 C16 120.2(5) . . ? C18 C17 H8 119.9 . . ? C16 C17 H8 119.9 . . ? C17 C18 C13 121.4(6) . . ? C17 C18 H9 119.3 . . ? C13 C18 H9 119.3 . . ? O8 C19 H10 109.5 . . ? O8 C19 H11 109.5 . . ? H10 C19 H11 109.5 . . ? O8 C19 H12 109.5 . . ? H10 C19 H12 109.5 . . ? H11 C19 H12 109.5 . . ? O5 C20 Fe2 176.2(6) . . ? O6 C21 Fe2 175.9(5) . . ? O7 C22 Fe2 178.3(6) . . ? Cl2 C23 Cl1 123.8(10) . . ? Cl2 C23 H14 106.4 . . ? Cl1 C23 H14 106.4 . . ? Cl2 C23 H13 106.4 . . ? Cl1 C23 H13 106.4 . . ? H14 C23 H13 106.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 Fe1 Fe2 C20 5.9(3) . . . . ? C2 Fe1 Fe2 C20 -94.2(4) . . . . ? C1 Fe1 Fe2 C20 98.5(3) . . . . ? C4 Fe1 Fe2 C20 -76.6(3) . . . . ? N1 Fe1 Fe2 C20 -171.6(2) . . . . ? C3 Fe1 Fe2 C21 114.9(5) . . . . ? C2 Fe1 Fe2 C21 14.8(6) . . . . ? C1 Fe1 Fe2 C21 -152.5(5) . . . . ? C4 Fe1 Fe2 C21 32.4(5) . . . . ? N1 Fe1 Fe2 C21 -62.7(4) . . . . ? C3 Fe1 Fe2 C22 -90.5(3) . . . . ? C2 Fe1 Fe2 C22 169.4(4) . . . . ? C1 Fe1 Fe2 C22 2.1(3) . . . . ? C4 Fe1 Fe2 C22 -173.1(3) . . . . ? N1 Fe1 Fe2 C22 91.9(2) . . . . ? C3 Fe1 Fe2 N2 179.7(2) . . . . ? C2 Fe1 Fe2 N2 79.7(4) . . . . ? C1 Fe1 Fe2 N2 -87.7(2) . . . . ? C4 Fe1 Fe2 N2 97.2(2) . . . . ? N1 Fe1 Fe2 N2 2.21(17) . . . . ? C3 Fe1 Fe2 C4 82.5(3) . . . . ? C2 Fe1 Fe2 C4 -17.5(4) . . . . ? C1 Fe1 Fe2 C4 175.1(3) . . . . ? N1 Fe1 Fe2 C4 -95.0(2) . . . . ? C3 Fe1 N1 C12 162.7(12) . . . . ? C2 Fe1 N1 C12 24.9(5) . . . . ? C1 Fe1 N1 C12 -85.2(5) . . . . ? C4 Fe1 N1 C12 126.7(5) . . . . ? Fe2 Fe1 N1 C12 177.0(5) . . . . ? C3 Fe1 N1 N2 -17.4(14) . . . . ? C2 Fe1 N1 N2 -155.3(3) . . . . ? C1 Fe1 N1 N2 94.6(3) . . . . ? C4 Fe1 N1 N2 -53.4(3) . . . . ? Fe2 Fe1 N1 N2 -3.1(2) . . . . ? C12 N1 N2 C5 1.4(6) . . . . ? Fe1 N1 N2 C5 -178.4(4) . . . . ? C12 N1 N2 Fe2 -176.1(3) . . . . ? Fe1 N1 N2 Fe2 4.1(3) . . . . ? C20 Fe2 N2 C5 -147.3(11) . . . . ? C21 Fe2 N2 C5 -22.9(5) . . . . ? C22 Fe2 N2 C5 81.4(5) . . . . ? C4 Fe2 N2 C5 -130.8(5) . . . . ? Fe1 Fe2 N2 C5 179.6(5) . . . . ? C20 Fe2 N2 N1 29.8(13) . . . . ? C21 Fe2 N2 N1 154.3(3) . . . . ? C22 Fe2 N2 N1 -101.4(3) . . . . ? C4 Fe2 N2 N1 46.3(3) . . . . ? Fe1 Fe2 N2 N1 -3.2(2) . . . . ? C3 Fe1 C1 O1 35(12) . . . . ? C2 Fe1 C1 O1 124(12) . . . . ? C4 Fe1 C1 O1 -56(12) . . . . ? N1 Fe1 C1 O1 -136(12) . . . . ? Fe2 Fe1 C1 O1 -63(12) . . . . ? C3 Fe1 C2 O2 11(4) . . . . ? C1 Fe1 C2 O2 -80(4) . . . . ? C4 Fe1 C2 O2 99(4) . . . . ? N1 Fe1 C2 O2 -176(4) . . . . ? Fe2 Fe1 C2 O2 113(4) . . . . ? C2 Fe1 C3 O3 39(23) . . . . ? C1 Fe1 C3 O3 148(23) . . . . ? C4 Fe1 C3 O3 -64(23) . . . . ? N1 Fe1 C3 O3 -100(23) . . . . ? Fe2 Fe1 C3 O3 -114(23) . . . . ? C3 Fe1 C4 O4 76.0(7) . . . . ? C2 Fe1 C4 O4 -12.1(7) . . . . ? C1 Fe1 C4 O4 167.1(6) . . . . ? N1 Fe1 C4 O4 -109.9(7) . . . . ? Fe2 Fe1 C4 O4 176.2(8) . . . . ? C3 Fe1 C4 Fe2 -100.3(2) . . . . ? C2 Fe1 C4 Fe2 171.6(2) . . . . ? C1 Fe1 C4 Fe2 -9.1(5) . . . . ? N1 Fe1 C4 Fe2 73.88(17) . . . . ? C20 Fe2 C4 O4 -71.6(7) . . . . ? C21 Fe2 C4 O4 17.4(7) . . . . ? C22 Fe2 C4 O4 -163.4(6) . . . . ? N2 Fe2 C4 O4 111.6(7) . . . . ? Fe1 Fe2 C4 O4 -176.3(8) . . . . ? C20 Fe2 C4 Fe1 104.7(2) . . . . ? C21 Fe2 C4 Fe1 -166.3(2) . . . . ? C22 Fe2 C4 Fe1 12.9(5) . . . . ? N2 Fe2 C4 Fe1 -72.11(17) . . . . ? N1 N2 C5 C6 -2.3(7) . . . . ? Fe2 N2 C5 C6 174.5(3) . . . . ? N2 C5 C6 C7 -177.5(5) . . . . ? N2 C5 C6 C11 1.1(7) . . . . ? C5 C6 C7 C8 177.6(5) . . . . ? C11 C6 C7 C8 -0.9(8) . . . . ? C6 C7 C8 C9 1.6(10) . . . . ? C7 C8 C9 C10 -2.3(10) . . . . ? C8 C9 C10 C11 2.3(9) . . . . ? C9 C10 C11 C6 -1.6(8) . . . . ? C9 C10 C11 C12 179.9(5) . . . . ? C5 C6 C11 C10 -177.7(5) . . . . ? C7 C6 C11 C10 0.9(8) . . . . ? C5 C6 C11 C12 0.9(7) . . . . ? C7 C6 C11 C12 179.5(5) . . . . ? N2 N1 C12 C11 0.6(7) . . . . ? Fe1 N1 C12 C11 -179.6(3) . . . . ? N2 N1 C12 C13 -179.2(4) . . . . ? Fe1 N1 C12 C13 0.6(7) . . . . ? C10 C11 C12 N1 176.8(5) . . . . ? C6 C11 C12 N1 -1.7(7) . . . . ? C10 C11 C12 C13 -3.3(8) . . . . ? C6 C11 C12 C13 178.1(5) . . . . ? N1 C12 C13 C18 77.1(6) . . . . ? C11 C12 C13 C18 -102.7(6) . . . . ? N1 C12 C13 C14 -106.5(6) . . . . ? C11 C12 C13 C14 73.7(7) . . . . ? C18 C13 C14 C15 -2.6(9) . . . . ? C12 C13 C14 C15 -179.1(5) . . . . ? C13 C14 C15 C16 0.7(10) . . . . ? C19 O8 C16 C17 -11.3(11) . . . . ? C19 O8 C16 C15 168.9(7) . . . . ? C14 C15 C16 O8 -178.7(6) . . . . ? C14 C15 C16 C17 1.4(10) . . . . ? O8 C16 C17 C18 178.7(6) . . . . ? C15 C16 C17 C18 -1.5(10) . . . . ? C16 C17 C18 C13 -0.6(10) . . . . ? C14 C13 C18 C17 2.6(9) . . . . ? C12 C13 C18 C17 179.1(5) . . . . ? C21 Fe2 C20 O5 -98(9) . . . . ? C22 Fe2 C20 O5 158(9) . . . . ? N2 Fe2 C20 O5 27(10) . . . . ? C4 Fe2 C20 O5 10(9) . . . . ? Fe1 Fe2 C20 O5 58(9) . . . . ? C20 Fe2 C21 O6 -57(7) . . . . ? C22 Fe2 C21 O6 38(7) . . . . ? N2 Fe2 C21 O6 132(7) . . . . ? C4 Fe2 C21 O6 -142(7) . . . . ? Fe1 Fe2 C21 O6 -168(7) . . . . ? C20 Fe2 C22 O7 42(20) . . . . ? C21 Fe2 C22 O7 -50(20) . . . . ? N2 Fe2 C22 O7 -146(20) . . . . ? C4 Fe2 C22 O7 131(20) . . . . ? Fe1 Fe2 C22 O7 141(20) . . . . ? _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.888 _refine_diff_density_max 0.914 _refine_diff_density_min -0.846 _refine_diff_density_rms 0.104