Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Xiaojun Peng' _publ_contact_author_address ; Dalian University of Technology State Key Laboratory of Fine Chemicals, Dalian University of Technology Dalian 116012 CHINA ; _publ_contact_author_email PENGXJ@DLUT.EDU.CN _publ_section_title ; Selenium-bridged diiron hexa-carbonyl complexes as biomimetic models for the active site of Fe-Fe hydrogenases ; loop_ _publ_author_name 'Xiaojun Peng' 'Jiangli Fan' 'Shang Gao' 'Jun Hou' 'Shiguo Sun' ; Xing Zhao ; data_1 _database_code_depnum_ccdc_archive 'CCDC 665465' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 Fe2 N2 O8 Se2' _chemical_formula_sum 'C14 H8 Fe2 N2 O8 Se2' _chemical_formula_weight 601.84 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' Se Se -0.0929 2.2259 '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) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.7173(3) _cell_length_b 10.5330(4) _cell_length_c 11.9968(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.189(2) _cell_angle_gamma 90.00 _cell_volume 945.43(6) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2313 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 21.25 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.114 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 5.429 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4098 _exptl_absorpt_correction_T_max 0.8992 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 12039 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4072 _reflns_number_gt 3153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0047P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.018(9) _refine_ls_number_reflns 4072 _refine_ls_number_parameters 253 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0551 _refine_ls_wR_factor_gt 0.0493 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.47046(6) 0.05729(5) 0.86585(4) 0.03982(13) Uani 1 1 d . . . Se2 Se 0.57143(7) 0.24358(5) 0.67297(4) 0.04441(15) Uani 1 1 d . . . Fe1 Fe 0.40301(9) 0.27172(6) 0.81358(5) 0.03988(19) Uani 1 1 d . . . Fe2 Fe 0.72190(9) 0.18697(6) 0.86477(6) 0.03918(19) Uani 1 1 d . . . N1 N 0.5000(6) -0.0291(4) 0.6400(3) 0.0489(11) Uani 1 1 d . . . C1 C 0.1852(7) 0.2579(6) 0.7199(4) 0.0480(13) Uani 1 1 d . . . C4 C 0.7570(7) 0.1981(6) 1.0160(5) 0.0600(16) Uani 1 1 d . . . C7 C 0.3994(7) -0.0477(6) 0.7241(4) 0.0533(14) Uani 1 1 d . . . H7A H 0.4085 -0.1364 0.7465 0.064 Uiso 1 1 calc R . . H7B H 0.2746 -0.0307 0.6882 0.064 Uiso 1 1 calc R . . C8 C 0.4684(7) 0.0896(5) 0.5808(4) 0.0566(16) Uani 1 1 d . . . H8A H 0.3403 0.1014 0.5536 0.068 Uiso 1 1 calc R . . H8B H 0.5174 0.0850 0.5138 0.068 Uiso 1 1 calc R . . C2 C 0.3357(7) 0.2858(5) 0.9457(5) 0.0493(14) Uani 1 1 d . . . C10 C 0.7765(7) -0.0619(5) 0.5815(4) 0.0478(13) Uani 1 1 d . . . H10A H 0.7626 0.0172 0.5460 0.057 Uiso 1 1 calc R . . C14 C 0.6760(7) -0.2209(5) 0.6910(4) 0.0489(13) Uani 1 1 d . . . H14A H 0.5941 -0.2503 0.7304 0.059 Uiso 1 1 calc R . . C5 C 0.8464(8) 0.3281(6) 0.8651(4) 0.0510(14) Uani 1 1 d . . . C9 C 0.6513(7) -0.1025(5) 0.6389(4) 0.0424(12) Uani 1 1 d . . . C12 C 0.9396(6) -0.2525(5) 0.6277(4) 0.0430(12) Uani 1 1 d . . . C13 C 0.8182(7) -0.2946(5) 0.6854(4) 0.0514(14) Uani 1 1 d . . . H13A H 0.8330 -0.3738 0.7209 0.062 Uiso 1 1 calc R . . C11 C 0.9208(7) -0.1358(5) 0.5757(4) 0.0466(13) Uani 1 1 d . . . H11A H 1.0042 -0.1071 0.5371 0.056 Uiso 1 1 calc R . . O7 O 1.2126(5) -0.2868(4) 0.5855(3) 0.0679(12) Uani 1 1 d . . . O8 O 1.0821(6) -0.4470(5) 0.6440(3) 0.0801(13) Uani 1 1 d . . . O2 O 0.2866(6) 0.2913(4) 1.0276(3) 0.0772(13) Uani 1 1 d . . . N2 N 1.0907(8) -0.3336(5) 0.6186(4) 0.0567(13) Uani 1 1 d . . . C6 C 0.8916(7) 0.0724(6) 0.8569(4) 0.0486(14) Uani 1 1 d . . . O4 O 0.7821(6) 0.2103(5) 1.1139(3) 0.0942(16) Uani 1 1 d . . . O5 O 0.9238(6) 0.4209(4) 0.8667(4) 0.0782(13) Uani 1 1 d . . . O1 O 0.0473(5) 0.2419(5) 0.6599(3) 0.0719(12) Uani 1 1 d . . . O6 O 1.0025(6) 0.0022(4) 0.8552(4) 0.0754(14) Uani 1 1 d . . . C3 C 0.4476(8) 0.4383(7) 0.8077(5) 0.0573(15) Uani 1 1 d . . . O3 O 0.4840(6) 0.5436(4) 0.8072(4) 0.0847(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.0403(3) 0.0383(3) 0.0420(2) 0.0046(2) 0.0121(2) -0.0021(3) Se2 0.0450(3) 0.0495(4) 0.0403(3) 0.0118(2) 0.0136(2) 0.0056(3) Fe1 0.0382(4) 0.0397(5) 0.0427(4) 0.0041(3) 0.0116(3) 0.0035(3) Fe2 0.0347(5) 0.0419(4) 0.0399(4) 0.0060(3) 0.0073(3) -0.0007(3) N1 0.055(3) 0.048(3) 0.044(2) -0.004(2) 0.013(2) 0.001(2) C1 0.050(3) 0.056(3) 0.043(3) 0.007(3) 0.021(3) 0.008(3) C4 0.041(3) 0.074(4) 0.059(3) 0.011(3) 0.000(3) -0.012(3) C7 0.044(3) 0.057(4) 0.063(3) -0.013(3) 0.021(3) -0.003(3) C8 0.061(4) 0.068(4) 0.035(3) -0.006(3) 0.000(2) 0.020(3) C2 0.047(3) 0.046(3) 0.054(3) -0.005(3) 0.011(3) -0.006(3) C10 0.061(4) 0.039(3) 0.046(3) 0.006(2) 0.017(3) 0.005(3) C14 0.059(4) 0.047(3) 0.045(3) 0.004(2) 0.020(2) -0.006(3) C5 0.044(3) 0.060(4) 0.049(3) 0.006(3) 0.010(3) -0.002(3) C9 0.046(3) 0.044(3) 0.038(3) -0.009(2) 0.011(2) 0.002(3) C12 0.046(3) 0.036(3) 0.044(3) -0.006(2) 0.006(2) 0.001(3) C13 0.065(4) 0.034(3) 0.052(3) 0.003(2) 0.010(3) 0.003(3) C11 0.052(4) 0.049(3) 0.040(3) 0.000(2) 0.013(2) -0.006(3) O7 0.056(3) 0.068(3) 0.079(3) -0.017(2) 0.015(2) 0.006(2) O8 0.097(4) 0.045(3) 0.098(3) -0.006(3) 0.024(2) 0.018(3) O2 0.101(3) 0.084(3) 0.056(2) -0.009(2) 0.035(2) 0.001(3) N2 0.070(4) 0.052(3) 0.044(3) -0.017(2) 0.008(3) 0.005(3) C6 0.036(3) 0.056(4) 0.049(3) 0.004(3) 0.002(2) -0.004(3) O4 0.092(3) 0.140(5) 0.044(2) -0.003(3) 0.005(2) -0.035(3) O5 0.077(3) 0.061(3) 0.097(3) 0.003(2) 0.024(3) -0.026(3) O1 0.045(2) 0.111(4) 0.055(2) 0.016(3) 0.0027(19) -0.007(3) O6 0.054(3) 0.068(3) 0.099(3) -0.006(2) 0.009(2) 0.020(2) C3 0.052(4) 0.065(4) 0.062(3) 0.008(3) 0.027(3) 0.010(3) O3 0.098(3) 0.042(3) 0.122(3) 0.006(3) 0.041(3) -0.005(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 Se1 C7 1.990(5) . ? Se1 Fe1 2.3676(8) . ? Se1 Fe2 2.3756(9) . ? Se2 C8 2.013(5) . ? Se2 Fe2 2.3850(8) . ? Se2 Fe1 2.3870(8) . ? Fe1 C1 1.785(5) . ? Fe1 C2 1.791(6) . ? Fe1 C3 1.793(7) . ? Fe1 Fe2 2.5475(10) . ? Fe2 C5 1.769(6) . ? Fe2 C4 1.771(6) . ? Fe2 C6 1.801(6) . ? N1 C9 1.403(6) . ? N1 C8 1.429(6) . ? N1 C7 1.430(6) . ? C1 O1 1.141(5) . ? C4 O4 1.150(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C2 O2 1.138(6) . ? C10 C11 1.375(7) . ? C10 C9 1.384(7) . ? C10 H10A 0.9300 . ? C14 C13 1.359(7) . ? C14 C9 1.388(7) . ? C14 H14A 0.9300 . ? C5 O5 1.144(6) . ? C12 C13 1.368(6) . ? C12 C11 1.370(7) . ? C12 N2 1.471(7) . ? C13 H13A 0.9300 . ? C11 H11A 0.9300 . ? O7 N2 1.212(6) . ? O8 N2 1.239(6) . ? C6 O6 1.135(6) . ? C3 O3 1.145(7) . ? 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 C7 Se1 Fe1 107.89(17) . . ? C7 Se1 Fe2 111.68(16) . . ? Fe1 Se1 Fe2 64.97(3) . . ? C8 Se2 Fe2 111.21(14) . . ? C8 Se2 Fe1 106.15(16) . . ? Fe2 Se2 Fe1 64.53(3) . . ? C1 Fe1 C2 97.5(2) . . ? C1 Fe1 C3 102.4(3) . . ? C2 Fe1 C3 93.1(2) . . ? C1 Fe1 Se1 101.61(19) . . ? C2 Fe1 Se1 86.41(17) . . ? C3 Fe1 Se1 155.82(18) . . ? C1 Fe1 Se2 97.86(15) . . ? C2 Fe1 Se2 164.16(16) . . ? C3 Fe1 Se2 87.16(17) . . ? Se1 Fe1 Se2 86.92(3) . . ? C1 Fe1 Fe2 145.95(17) . . ? C2 Fe1 Fe2 106.77(16) . . ? C3 Fe1 Fe2 99.73(18) . . ? Se1 Fe1 Fe2 57.67(2) . . ? Se2 Fe1 Fe2 57.70(2) . . ? C5 Fe2 C4 89.7(3) . . ? C5 Fe2 C6 99.3(3) . . ? C4 Fe2 C6 99.6(3) . . ? C5 Fe2 Se1 157.95(18) . . ? C4 Fe2 Se1 87.29(18) . . ? C6 Fe2 Se1 102.74(19) . . ? C5 Fe2 Se2 85.87(16) . . ? C4 Fe2 Se2 152.6(2) . . ? C6 Fe2 Se2 107.79(16) . . ? Se1 Fe2 Se2 86.78(3) . . ? C5 Fe2 Fe1 101.43(18) . . ? C4 Fe2 Fe1 96.89(18) . . ? C6 Fe2 Fe1 153.44(17) . . ? Se1 Fe2 Fe1 57.36(3) . . ? Se2 Fe2 Fe1 57.77(2) . . ? C9 N1 C8 121.2(4) . . ? C9 N1 C7 121.9(4) . . ? C8 N1 C7 114.5(5) . . ? O1 C1 Fe1 176.2(6) . . ? O4 C4 Fe2 177.3(6) . . ? N1 C7 Se1 116.3(4) . . ? N1 C7 H7A 108.2 . . ? Se1 C7 H7A 108.2 . . ? N1 C7 H7B 108.2 . . ? Se1 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? N1 C8 Se2 115.8(3) . . ? N1 C8 H8A 108.3 . . ? Se2 C8 H8A 108.3 . . ? N1 C8 H8B 108.3 . . ? Se2 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? O2 C2 Fe1 176.9(5) . . ? C11 C10 C9 121.6(5) . . ? C11 C10 H10A 119.2 . . ? C9 C10 H10A 119.2 . . ? C13 C14 C9 121.0(5) . . ? C13 C14 H14A 119.5 . . ? C9 C14 H14A 119.5 . . ? O5 C5 Fe2 178.2(6) . . ? C10 C9 C14 117.8(5) . . ? C10 C9 N1 121.2(5) . . ? C14 C9 N1 120.9(5) . . ? C13 C12 C11 120.9(5) . . ? C13 C12 N2 120.2(5) . . ? C11 C12 N2 119.0(5) . . ? C14 C13 C12 120.0(5) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C12 C11 C10 118.7(5) . . ? C12 C11 H11A 120.6 . . ? C10 C11 H11A 120.6 . . ? O7 N2 O8 124.4(5) . . ? O7 N2 C12 118.8(5) . . ? O8 N2 C12 116.8(5) . . ? O6 C6 Fe2 177.6(5) . . ? O3 C3 Fe1 176.7(6) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.385 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.083 # Attachment 'Complex_8.cif' data_good _database_code_depnum_ccdc_archive 'CCDC 665466' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Fe2 N O6 Se2' _chemical_formula_sum 'C14 H9 Fe2 N O6 Se2' _chemical_formula_weight 556.84 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.0764(6) _cell_length_b 12.3471(8) _cell_length_c 17.7225(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.866(4) _cell_angle_gamma 90.00 _cell_volume 1766.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7501 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 28.80 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.094 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 5.793 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2508 _exptl_absorpt_correction_T_max 0.4770 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 22004 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4270 _reflns_number_gt 3523 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0259P)^2^+0.6223P] 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 SHELXL _refine_ls_extinction_coef 0.0235(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4270 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0596 _refine_ls_wR_factor_gt 0.0569 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se2 Se 0.76190(3) 0.575920(18) 0.249049(13) 0.04189(8) Uani 1 1 d . . . Se1 Se 0.95335(3) 0.348741(17) 0.287363(15) 0.04523(9) Uani 1 1 d . . . Fe1 Fe 0.71901(4) 0.43664(3) 0.33910(2) 0.04133(10) Uani 1 1 d . . . Fe2 Fe 0.99905(4) 0.53030(2) 0.326169(18) 0.03611(9) Uani 1 1 d . . . N1 N 0.9118(3) 0.44082(17) 0.13450(12) 0.0524(5) Uani 1 1 d . . . O3 O 0.5313(3) 0.5945(2) 0.42462(14) 0.0780(6) Uani 1 1 d . . . O5 O 0.9478(3) 0.73428(16) 0.40465(13) 0.0771(7) Uani 1 1 d . . . O4 O 1.1690(3) 0.43638(18) 0.45805(13) 0.0800(7) Uani 1 1 d . . . C4 C 1.1029(3) 0.47356(19) 0.40650(15) 0.0496(6) Uani 1 1 d . . . O6 O 1.3019(3) 0.6002(2) 0.25271(13) 0.0738(6) Uani 1 1 d . . . C5 C 0.9667(4) 0.65466(19) 0.37421(15) 0.0485(6) Uani 1 1 d . . . C6 C 1.1820(3) 0.5719(2) 0.27735(15) 0.0487(6) Uani 1 1 d . . . O1 O 0.4362(3) 0.32780(19) 0.26372(15) 0.0778(7) Uani 1 1 d . . . C9 C 1.0515(3) 0.4966(2) 0.10906(13) 0.0469(6) Uani 1 1 d . . . C3 C 0.6049(4) 0.5332(2) 0.39152(16) 0.0527(6) Uani 1 1 d . . . C8 C 0.7654(4) 0.4980(3) 0.14886(15) 0.0578(7) Uani 1 1 d . . . H8A H 0.6735 0.4474 0.1463 0.069 Uiso 1 1 calc R . . H8B H 0.7470 0.5508 0.1089 0.069 Uiso 1 1 calc R . . C1 C 0.5468(4) 0.3686(2) 0.29335(16) 0.0517(6) Uani 1 1 d . . . C7 C 0.9265(5) 0.3407(2) 0.17435(16) 0.0621(8) Uani 1 1 d . . . H7A H 1.0209 0.3019 0.1553 0.074 Uiso 1 1 calc R . . H7B H 0.8286 0.2978 0.1622 0.074 Uiso 1 1 calc R . . O2 O 0.7742(3) 0.2992(2) 0.47183(14) 0.0835(7) Uani 1 1 d . . . C14 C 1.1979(4) 0.4415(2) 0.09481(17) 0.0639(8) Uani 1 1 d . . . H14A H 1.2047 0.3673 0.1032 0.077 Uiso 1 1 calc R . . C2 C 0.7528(4) 0.3524(2) 0.42001(17) 0.0548(6) Uani 1 1 d . . . C10 C 1.0470(4) 0.6064(3) 0.09473(18) 0.0647(8) Uani 1 1 d . . . H10A H 0.9513 0.6455 0.1037 0.078 Uiso 1 1 calc R . . C11 C 1.1832(6) 0.6584(3) 0.0673(2) 0.0799(10) Uani 1 1 d . . . H11A H 1.1768 0.7322 0.0571 0.096 Uiso 1 1 calc R . . C13 C 1.3324(4) 0.4965(3) 0.0684(2) 0.0767(9) Uani 1 1 d . . . H13A H 1.4295 0.4587 0.0598 0.092 Uiso 1 1 calc R . . C12 C 1.3266(5) 0.6049(3) 0.05462(19) 0.0798(10) Uani 1 1 d . . . H12A H 1.4184 0.6413 0.0370 0.096 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 Se2 0.03688(13) 0.03866(13) 0.04974(14) 0.00419(9) -0.00449(10) 0.00431(9) Se1 0.04553(15) 0.02903(12) 0.06095(16) -0.00413(9) -0.00092(11) 0.00163(9) Fe1 0.03786(19) 0.03573(17) 0.0503(2) 0.00153(13) 0.00001(15) -0.00182(13) Fe2 0.03493(17) 0.02922(15) 0.04378(18) -0.00144(12) -0.00509(13) 0.00070(12) N1 0.0537(14) 0.0557(13) 0.0477(12) -0.0095(10) -0.0002(10) -0.0080(10) O3 0.0816(17) 0.0763(14) 0.0773(14) -0.0082(12) 0.0179(13) 0.0213(13) O5 0.1022(19) 0.0497(11) 0.0779(14) -0.0249(10) -0.0199(13) 0.0199(11) O4 0.0982(19) 0.0734(14) 0.0663(13) 0.0093(11) -0.0304(13) 0.0151(12) C4 0.0522(15) 0.0402(12) 0.0556(15) -0.0012(11) -0.0078(12) 0.0022(11) O6 0.0473(12) 0.0980(17) 0.0764(14) 0.0064(12) 0.0054(11) -0.0161(12) C5 0.0517(15) 0.0403(12) 0.0528(14) -0.0023(10) -0.0109(12) 0.0047(10) C6 0.0424(14) 0.0484(13) 0.0548(14) -0.0004(11) -0.0079(12) -0.0018(11) O1 0.0606(14) 0.0722(14) 0.0993(17) -0.0079(12) -0.0150(13) -0.0189(11) C9 0.0514(15) 0.0535(14) 0.0358(11) -0.0063(10) 0.0003(11) -0.0049(11) C3 0.0516(16) 0.0517(14) 0.0551(15) 0.0026(12) 0.0045(13) 0.0008(12) C8 0.0490(16) 0.0753(18) 0.0484(14) -0.0035(13) -0.0096(12) -0.0114(14) C1 0.0501(16) 0.0441(13) 0.0610(16) -0.0007(11) 0.0009(13) -0.0024(11) C7 0.082(2) 0.0466(14) 0.0584(16) -0.0166(12) 0.0084(15) -0.0166(14) O2 0.0909(18) 0.0806(15) 0.0784(15) 0.0335(13) -0.0078(14) -0.0052(13) C14 0.066(2) 0.0618(17) 0.0641(17) -0.0009(14) 0.0037(15) 0.0064(14) C2 0.0517(16) 0.0497(14) 0.0629(16) 0.0050(12) 0.0005(13) -0.0046(12) C10 0.0633(19) 0.0587(17) 0.0723(19) 0.0035(14) 0.0056(16) 0.0045(14) C11 0.099(3) 0.0622(19) 0.079(2) 0.0140(16) 0.014(2) -0.0105(19) C13 0.056(2) 0.102(3) 0.072(2) 0.0008(19) 0.0126(17) 0.0066(19) C12 0.074(2) 0.102(3) 0.0643(19) 0.0060(18) 0.0168(18) -0.022(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 Se2 C8 2.021(3) . ? Se2 Fe1 2.3791(4) . ? Se2 Fe2 2.3840(4) . ? Se1 C7 2.010(3) . ? Se1 Fe2 2.3703(4) . ? Se1 Fe1 2.3903(5) . ? Fe1 C2 1.785(3) . ? Fe1 C3 1.786(3) . ? Fe1 C1 1.796(3) . ? Fe1 Fe2 2.5572(5) . ? Fe2 C4 1.773(3) . ? Fe2 C5 1.779(2) . ? Fe2 C6 1.811(3) . ? N1 C8 1.407(4) . ? N1 C9 1.408(4) . ? N1 C7 1.426(4) . ? O3 C3 1.137(3) . ? O5 C5 1.134(3) . ? O4 C4 1.139(3) . ? O6 C6 1.131(4) . ? O1 C1 1.139(3) . ? C9 C10 1.379(4) . ? C9 C14 1.394(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? O2 C2 1.138(3) . ? C14 C13 1.375(5) . ? C14 H14A 0.9300 . ? C10 C11 1.376(5) . ? C10 H10A 0.9300 . ? C11 C12 1.359(6) . ? C11 H11A 0.9300 . ? C13 C12 1.360(6) . ? C13 H13A 0.9300 . ? C12 H12A 0.9300 . ? 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 C8 Se2 Fe1 104.58(9) . . ? C8 Se2 Fe2 110.94(9) . . ? Fe1 Se2 Fe2 64.943(13) . . ? C7 Se1 Fe2 110.27(7) . . ? C7 Se1 Fe1 110.08(11) . . ? Fe2 Se1 Fe1 64.979(13) . . ? C2 Fe1 C3 92.24(13) . . ? C2 Fe1 C1 100.72(12) . . ? C3 Fe1 C1 98.18(13) . . ? C2 Fe1 Se2 159.73(9) . . ? C3 Fe1 Se2 87.43(9) . . ? C1 Fe1 Se2 99.38(9) . . ? C2 Fe1 Se1 86.63(10) . . ? C3 Fe1 Se1 158.60(10) . . ? C1 Fe1 Se1 103.03(9) . . ? Se2 Fe1 Se1 86.359(15) . . ? C2 Fe1 Fe2 102.87(10) . . ? C3 Fe1 Fe2 102.56(9) . . ? C1 Fe1 Fe2 147.72(10) . . ? Se2 Fe1 Fe2 57.620(12) . . ? Se1 Fe1 Fe2 57.132(13) . . ? C4 Fe2 C5 91.71(11) . . ? C4 Fe2 C6 97.09(12) . . ? C5 Fe2 C6 96.82(13) . . ? C4 Fe2 Se1 85.66(8) . . ? C5 Fe2 Se1 158.62(10) . . ? C6 Fe2 Se1 104.56(8) . . ? C4 Fe2 Se2 154.69(10) . . ? C5 Fe2 Se2 86.71(8) . . ? C6 Fe2 Se2 108.18(8) . . ? Se1 Fe2 Se2 86.703(13) . . ? C4 Fe2 Fe1 98.40(9) . . ? C5 Fe2 Fe1 101.73(10) . . ? C6 Fe2 Fe1 155.36(8) . . ? Se1 Fe2 Fe1 57.888(12) . . ? Se2 Fe2 Fe1 57.438(12) . . ? C8 N1 C9 119.9(2) . . ? C8 N1 C7 113.7(3) . . ? C9 N1 C7 121.8(3) . . ? O4 C4 Fe2 179.5(3) . . ? O5 C5 Fe2 179.2(3) . . ? O6 C6 Fe2 174.1(2) . . ? C10 C9 C14 117.6(3) . . ? C10 C9 N1 121.5(3) . . ? C14 C9 N1 120.9(3) . . ? O3 C3 Fe1 179.5(3) . . ? N1 C8 Se2 115.69(18) . . ? N1 C8 H8A 108.4 . . ? Se2 C8 H8A 108.4 . . ? N1 C8 H8B 108.4 . . ? Se2 C8 H8B 108.4 . . ? H8A C8 H8B 107.4 . . ? O1 C1 Fe1 178.3(3) . . ? N1 C7 Se1 117.07(17) . . ? N1 C7 H7A 108.0 . . ? Se1 C7 H7A 108.0 . . ? N1 C7 H7B 108.0 . . ? Se1 C7 H7B 108.0 . . ? H7A C7 H7B 107.3 . . ? C13 C14 C9 120.3(3) . . ? C13 C14 H14A 119.8 . . ? C9 C14 H14A 119.8 . . ? O2 C2 Fe1 179.7(3) . . ? C11 C10 C9 120.5(3) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C12 C11 C10 121.8(3) . . ? C12 C11 H11A 119.1 . . ? C10 C11 H11A 119.1 . . ? C12 C13 C14 121.6(4) . . ? C12 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 . . ? C11 C12 C13 118.2(3) . . ? C11 C12 H12A 120.9 . . ? C13 C12 H12A 120.9 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.919 _refine_diff_density_min -0.837 _refine_diff_density_rms 0.090 # Attachment 'Complex_9.cif' data_9 _database_code_depnum_ccdc_archive 'CCDC 665467' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H11 Fe2 N O6 Se2' _chemical_formula_sum 'C15 H11 Fe2 N O6 Se2' _chemical_formula_weight 570.87 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' Se Se -0.0929 2.2259 '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 7.835(2) _cell_length_b 9.930(3) _cell_length_c 12.436(3) _cell_angle_alpha 100.133(3) _cell_angle_beta 101.395(3) _cell_angle_gamma 90.643(3) _cell_volume 932.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1715 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 24.33 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.033 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 5.489 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2033 _exptl_absorpt_correction_T_max 0.7786 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 5855 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 29.17 _reflns_number_total 4317 _reflns_number_gt 3093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0404P)^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 4317 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se2 Se 0.45420(5) 0.35626(4) 0.81659(3) 0.04076(12) Uani 1 1 d . . . Se1 Se 0.68173(6) 0.11352(4) 0.70829(3) 0.04072(12) Uani 1 1 d . . . Fe2 Fe 0.73799(7) 0.35257(6) 0.77546(5) 0.03660(15) Uani 1 1 d . . . Fe1 Fe 0.46753(7) 0.25605(6) 0.63003(4) 0.03606(15) Uani 1 1 d . . . N1 N 0.5535(5) 0.1159(3) 0.9155(3) 0.0431(8) Uani 1 1 d . . . O3 O 0.3156(5) 0.4998(3) 0.5555(3) 0.0688(10) Uani 1 1 d . . . O4 O 0.9671(5) 0.3604(4) 0.6178(3) 0.0774(11) Uani 1 1 d . . . O2 O 0.5889(5) 0.1855(4) 0.4200(3) 0.0738(11) Uani 1 1 d . . . C14 C 0.8021(6) 0.0568(4) 1.0480(3) 0.0417(10) Uani 1 1 d . . . H14A H 0.8108 -0.0242 0.9993 0.050 Uiso 1 1 calc R . . C8 C 0.4107(5) 0.2001(4) 0.8914(3) 0.0441(10) Uani 1 1 d . . . H8A H 0.3753 0.2371 0.9608 0.053 Uiso 1 1 calc R . . H8B H 0.3138 0.1430 0.8442 0.053 Uiso 1 1 calc R . . C2 C 0.5428(6) 0.2121(4) 0.5019(4) 0.0476(11) Uani 1 1 d . . . O5 O 0.7089(5) 0.6493(3) 0.8044(3) 0.0781(11) Uani 1 1 d . . . C3 C 0.3739(6) 0.4060(5) 0.5859(3) 0.0465(11) Uani 1 1 d . . . C9 C 0.6775(5) 0.1495(4) 1.0159(3) 0.0402(9) Uani 1 1 d . . . C4 C 0.8769(6) 0.3542(5) 0.6790(4) 0.0494(11) Uani 1 1 d . . . C7 C 0.5864(6) 0.0255(4) 0.8199(3) 0.0472(11) Uani 1 1 d . . . H7A H 0.4784 -0.0250 0.7818 0.057 Uiso 1 1 calc R . . H7B H 0.6683 -0.0404 0.8453 0.057 Uiso 1 1 calc R . . C10 C 0.6755(6) 0.2712(4) 1.0888(3) 0.0500(12) Uani 1 1 d . . . H10A H 0.5978 0.3368 1.0685 0.060 Uiso 1 1 calc R . . C5 C 0.7232(6) 0.5348(5) 0.7930(4) 0.0508(11) Uani 1 1 d . . . O6 O 1.0190(5) 0.3351(4) 0.9671(3) 0.0792(11) Uani 1 1 d . . . O1 O 0.1576(5) 0.0716(4) 0.5849(3) 0.0822(12) Uani 1 1 d . . . C12 C 0.9050(6) 0.2032(5) 1.2262(3) 0.0471(11) Uani 1 1 d . . . C13 C 0.9116(6) 0.0844(4) 1.1505(4) 0.0461(10) Uani 1 1 d . . . H13A H 0.9932 0.0210 1.1699 0.055 Uiso 1 1 calc R . . C6 C 0.9052(6) 0.3436(5) 0.8968(4) 0.0514(11) Uani 1 1 d . . . C1 C 0.2764(6) 0.1425(4) 0.5996(4) 0.0491(11) Uani 1 1 d . . . C11 C 0.7876(6) 0.2969(5) 1.1917(4) 0.0554(12) Uani 1 1 d . . . H11A H 0.7838 0.3800 1.2391 0.067 Uiso 1 1 calc R . . C15 C 1.0205(7) 0.2314(5) 1.3414(4) 0.0655(14) Uani 1 1 d . . . H15A H 0.9953 0.3186 1.3808 0.098 Uiso 1 1 calc R . . H15B H 1.1405 0.2326 1.3350 0.098 Uiso 1 1 calc R . . H15C H 0.9988 0.1610 1.3816 0.098 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 Se2 0.0392(2) 0.0414(2) 0.0424(2) 0.00913(18) 0.00854(18) 0.00616(18) Se1 0.0458(3) 0.0364(2) 0.0379(2) 0.00512(17) 0.00467(18) 0.00742(18) Fe2 0.0331(3) 0.0375(3) 0.0368(3) 0.0039(2) 0.0039(2) -0.0005(2) Fe1 0.0381(3) 0.0344(3) 0.0331(3) 0.0076(2) -0.0003(2) 0.0000(2) N1 0.047(2) 0.045(2) 0.0353(18) 0.0118(15) -0.0001(15) 0.0038(17) O3 0.085(3) 0.054(2) 0.075(2) 0.0329(18) 0.017(2) 0.022(2) O4 0.066(2) 0.096(3) 0.081(3) 0.021(2) 0.037(2) 0.003(2) O2 0.109(3) 0.067(2) 0.046(2) 0.0016(17) 0.024(2) -0.002(2) C14 0.047(3) 0.039(2) 0.041(2) 0.0116(18) 0.0103(19) 0.0062(19) C8 0.040(2) 0.051(3) 0.044(2) 0.0157(19) 0.0084(19) 0.000(2) C2 0.060(3) 0.038(2) 0.041(2) 0.0058(19) 0.003(2) 0.002(2) O5 0.081(3) 0.038(2) 0.121(3) 0.016(2) 0.032(2) 0.0035(18) C3 0.049(3) 0.048(3) 0.041(2) 0.009(2) 0.005(2) 0.004(2) C9 0.048(3) 0.043(2) 0.034(2) 0.0151(18) 0.0117(18) 0.0012(19) C4 0.040(3) 0.050(3) 0.055(3) 0.003(2) 0.009(2) 0.001(2) C7 0.067(3) 0.035(2) 0.038(2) 0.0087(18) 0.003(2) -0.002(2) C10 0.057(3) 0.048(3) 0.045(3) 0.010(2) 0.007(2) 0.020(2) C5 0.041(3) 0.050(3) 0.063(3) 0.013(2) 0.011(2) -0.004(2) O6 0.059(2) 0.098(3) 0.069(2) 0.018(2) -0.018(2) -0.004(2) O1 0.059(2) 0.074(3) 0.103(3) 0.029(2) -0.015(2) -0.027(2) C12 0.043(3) 0.063(3) 0.038(2) 0.016(2) 0.0079(19) -0.001(2) C13 0.043(3) 0.049(3) 0.051(3) 0.020(2) 0.010(2) 0.010(2) C6 0.050(3) 0.046(3) 0.052(3) 0.003(2) 0.000(2) -0.008(2) C1 0.048(3) 0.044(3) 0.051(3) 0.018(2) -0.009(2) -0.003(2) C11 0.063(3) 0.057(3) 0.041(3) 0.002(2) 0.007(2) 0.014(2) C15 0.064(3) 0.087(4) 0.043(3) 0.016(3) 0.000(2) -0.004(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 Se2 C8 2.002(4) . ? Se2 Fe2 2.3772(9) . ? Se2 Fe1 2.3811(9) . ? Se1 C7 2.018(4) . ? Se1 Fe1 2.3790(8) . ? Se1 Fe2 2.3792(9) . ? Fe2 C4 1.774(5) . ? Fe2 C5 1.792(5) . ? Fe2 C6 1.808(5) . ? Fe2 Fe1 2.5514(9) . ? Fe1 C2 1.791(5) . ? Fe1 C3 1.792(4) . ? Fe1 C1 1.801(5) . ? N1 C9 1.407(5) . ? N1 C8 1.420(5) . ? N1 C7 1.427(5) . ? O3 C3 1.133(5) . ? O4 C4 1.145(5) . ? O2 C2 1.136(5) . ? C14 C13 1.370(6) . ? C14 C9 1.398(5) . ? C14 H14A 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O5 C5 1.130(5) . ? C9 C10 1.380(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C10 C11 1.382(6) . ? C10 H10A 0.9300 . ? O6 C6 1.134(5) . ? O1 C1 1.127(5) . ? C12 C11 1.379(6) . ? C12 C13 1.382(6) . ? C12 C15 1.514(6) . ? C13 H13A 0.9300 . ? C11 H11A 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 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 C8 Se2 Fe2 111.12(12) . . ? C8 Se2 Fe1 105.82(13) . . ? Fe2 Se2 Fe1 64.85(2) . . ? C7 Se1 Fe1 108.45(13) . . ? C7 Se1 Fe2 110.35(11) . . ? Fe1 Se1 Fe2 64.85(3) . . ? C4 Fe2 C5 91.3(2) . . ? C4 Fe2 C6 97.6(2) . . ? C5 Fe2 C6 99.1(2) . . ? C4 Fe2 Se2 150.32(15) . . ? C5 Fe2 Se2 84.28(15) . . ? C6 Fe2 Se2 112.13(16) . . ? C4 Fe2 Se1 88.78(15) . . ? C5 Fe2 Se1 162.38(15) . . ? C6 Fe2 Se1 98.37(14) . . ? Se2 Fe2 Se1 86.92(2) . . ? C4 Fe2 Fe1 95.70(15) . . ? C5 Fe2 Fe1 104.93(15) . . ? C6 Fe2 Fe1 152.21(15) . . ? Se2 Fe2 Fe1 57.65(3) . . ? Se1 Fe2 Fe1 57.57(2) . . ? C2 Fe1 C3 90.22(19) . . ? C2 Fe1 C1 100.0(2) . . ? C3 Fe1 C1 100.4(2) . . ? C2 Fe1 Se1 87.76(14) . . ? C3 Fe1 Se1 159.08(15) . . ? C1 Fe1 Se1 100.43(13) . . ? C2 Fe1 Se2 161.52(15) . . ? C3 Fe1 Se2 88.56(14) . . ? C1 Fe1 Se2 98.36(15) . . ? Se1 Fe1 Se2 86.84(3) . . ? C2 Fe1 Fe2 104.99(15) . . ? C3 Fe1 Fe2 103.11(14) . . ? C1 Fe1 Fe2 145.32(14) . . ? Se1 Fe1 Fe2 57.58(3) . . ? Se2 Fe1 Fe2 57.50(2) . . ? C9 N1 C8 120.7(3) . . ? C9 N1 C7 123.0(3) . . ? C8 N1 C7 113.8(3) . . ? C13 C14 C9 120.6(4) . . ? C13 C14 H14A 119.7 . . ? C9 C14 H14A 119.7 . . ? N1 C8 Se2 116.0(3) . . ? N1 C8 H8A 108.3 . . ? Se2 C8 H8A 108.3 . . ? N1 C8 H8B 108.3 . . ? Se2 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? O2 C2 Fe1 179.0(4) . . ? O3 C3 Fe1 178.3(4) . . ? C10 C9 C14 117.5(4) . . ? C10 C9 N1 121.7(4) . . ? C14 C9 N1 120.8(4) . . ? O4 C4 Fe2 177.5(4) . . ? N1 C7 Se1 116.3(3) . . ? N1 C7 H7A 108.2 . . ? Se1 C7 H7A 108.2 . . ? N1 C7 H7B 108.2 . . ? Se1 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? C9 C10 C11 120.8(4) . . ? C9 C10 H10A 119.6 . . ? C11 C10 H10A 119.6 . . ? O5 C5 Fe2 178.0(4) . . ? C11 C12 C13 116.7(4) . . ? C11 C12 C15 120.8(4) . . ? C13 C12 C15 122.5(4) . . ? C14 C13 C12 122.3(4) . . ? C14 C13 H13A 118.9 . . ? C12 C13 H13A 118.9 . . ? O6 C6 Fe2 174.4(5) . . ? O1 C1 Fe1 177.3(4) . . ? C12 C11 C10 122.0(4) . . ? C12 C11 H11A 119.0 . . ? C10 C11 H11A 119.0 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.855 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.551 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.095