# 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 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Mallayan Andavar' _publ_contact_author_email PALANIM51@YAHOO.COM _publ_section_title ; Synthesis, Structure, and Reactivity of Iron(III) Complexes of cis-Facially Coordinating and Sterically Hindering 3N Ligands as Models for Catechol Dioxygenases ; loop_ _publ_author_name 'Mallayan Andavar' 'Thirumanasekaran Dhanalakshmi' 'Karuppasamy Sundaravel' 'Eringathodi Suresh' #[Fe(L2)Cl3] data_5mpksm _database_code_depnum_ccdc_archive 'CCDC 689797' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H17 Cl3 Fe N3' _chemical_formula_weight 341.47 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 9.1366(13) _cell_length_b 7.0925(10) _cell_length_c 21.654(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.442(3) _cell_angle_gamma 90.00 _cell_volume 1388.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATES _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 1.645 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6650 _exptl_absorpt_correction_T_max 0.9678 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8110 _diffrn_reflns_av_R_equivalents 0.0853 _diffrn_reflns_av_sigmaI/netI 0.1243 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3241 _reflns_number_gt 2209 _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 ORTEP _computing_publication_material ? _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^)+(0.0744P)^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 3241 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1198 _refine_ls_R_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.1826 _refine_ls_wR_factor_gt 0.1541 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.23852(10) -0.00947(12) 0.39900(4) 0.0089(2) Uani 1 d . . . Cl1 Cl 0.18451(18) -0.1583(2) 0.48783(7) 0.0142(4) Uani 1 d . . . Cl3 Cl 0.48226(17) -0.1229(2) 0.40433(7) 0.0132(4) Uani 1 d . . . Cl2 Cl 0.12228(17) -0.2152(2) 0.32749(7) 0.0149(4) Uani 1 d . . . N1 N 0.2928(6) 0.1918(7) 0.3308(2) 0.0115(11) Uani 1 d . . . N2 N 0.3344(6) 0.2206(7) 0.4566(2) 0.0116(11) Uani 1 d . . . H2A H 0.4014 0.1735 0.4939 0.02(2) Uiso 1 d . . . N3 N 0.0419(6) 0.1757(7) 0.4002(2) 0.0131(12) Uani 1 d . . . H3A H 0.0696 0.0674 0.4156 0.016 Uiso 1 calc R . . C1 C 0.2491(7) 0.1760(9) 0.2682(3) 0.0118(13) Uani 1 d . . . H1 H 0.1836 0.0805 0.2532 0.014 Uiso 1 calc R . . C2 C 0.2997(7) 0.2989(9) 0.2263(3) 0.0155(14) Uani 1 d . . . H2 H 0.2691 0.2859 0.1836 0.019 Uiso 1 calc R . . C3 C 0.3975(8) 0.4425(9) 0.2491(3) 0.0165(15) Uani 1 d . . . H3 H 0.4359 0.5239 0.2218 0.020 Uiso 1 calc R . . C4 C 0.4362(7) 0.4614(9) 0.3131(3) 0.0139(14) Uani 1 d . . . H4 H 0.4982 0.5589 0.3294 0.017 Uiso 1 calc R . . C5 C 0.3819(7) 0.3341(9) 0.3523(3) 0.0121(13) Uani 1 d . . . C6 C 0.4262(7) 0.3461(9) 0.4222(3) 0.0150(14) Uani 1 d . . . H6A H 0.5295 0.3109 0.4326 0.018 Uiso 1 calc R . . H6B H 0.4160 0.4753 0.4355 0.018 Uiso 1 calc R . . C7 C 0.2155(7) 0.3260(9) 0.4822(3) 0.0147(14) Uani 1 d . . . H7A H 0.2536 0.4457 0.4993 0.018 Uiso 1 calc R . . H7B H 0.1819 0.2539 0.5155 0.018 Uiso 1 calc R . . C8 C 0.0881(7) 0.3594(9) 0.4305(3) 0.0118(13) Uani 1 d . . . H8A H 0.0057 0.4156 0.4474 0.014 Uiso 1 calc R . . H8B H 0.1183 0.4454 0.3998 0.014 Uiso 1 calc R . . C9 C -0.0586(7) 0.2033(10) 0.3400(3) 0.0171(15) Uani 1 d . . . H9A H -0.0776 0.0817 0.3199 0.020 Uiso 1 calc R . . H9B H -0.0087 0.2813 0.3127 0.020 Uiso 1 calc R . . C10 C -0.2045(7) 0.2938(11) 0.3473(3) 0.0243(17) Uani 1 d . . . H10A H -0.2589 0.2120 0.3710 0.036 Uiso 1 calc R . . H10B H -0.2607 0.3151 0.3068 0.036 Uiso 1 calc R . . H10C H -0.1868 0.4120 0.3687 0.036 Uiso 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 0.0114(5) 0.0055(5) 0.0096(4) -0.0001(4) 0.0006(3) 0.0004(4) Cl1 0.0202(9) 0.0111(8) 0.0119(7) 0.0020(6) 0.0043(6) 0.0006(6) Cl3 0.0134(8) 0.0132(8) 0.0127(7) 0.0004(6) 0.0011(6) 0.0041(6) Cl2 0.0196(9) 0.0102(8) 0.0132(8) -0.0017(6) -0.0035(6) -0.0013(6) N1 0.012(3) 0.012(3) 0.010(2) -0.003(2) 0.001(2) -0.001(2) N2 0.015(3) 0.012(3) 0.008(2) 0.002(2) 0.000(2) 0.002(2) N3 0.012(3) 0.009(3) 0.017(3) 0.001(2) -0.006(2) 0.000(2) C1 0.010(3) 0.010(3) 0.014(3) -0.003(3) -0.001(3) 0.003(3) C2 0.016(4) 0.018(4) 0.012(3) 0.003(3) 0.002(3) 0.007(3) C3 0.026(4) 0.005(3) 0.020(3) 0.007(3) 0.012(3) 0.004(3) C4 0.013(3) 0.008(3) 0.021(3) -0.001(3) 0.002(3) 0.001(3) C5 0.008(3) 0.015(4) 0.013(3) 0.002(3) 0.001(3) -0.001(3) C6 0.017(3) 0.012(3) 0.016(3) -0.003(3) 0.002(3) -0.002(3) C7 0.014(3) 0.018(4) 0.011(3) -0.004(3) 0.001(3) -0.001(3) C8 0.015(3) 0.009(3) 0.011(3) 0.004(3) 0.000(3) 0.004(3) C9 0.013(3) 0.020(4) 0.018(3) 0.000(3) -0.001(3) 0.000(3) C10 0.014(4) 0.034(5) 0.024(4) 0.006(3) -0.001(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 Fe1 N2 2.160(5) . ? Fe1 N1 2.163(5) . ? Fe1 N3 2.229(5) . ? Fe1 Cl2 2.2743(17) . ? Fe1 Cl1 2.3101(17) . ? Fe1 Cl3 2.3547(18) . ? N1 C5 1.336(8) . ? N1 C1 1.361(7) . ? N2 C7 1.492(8) . ? N2 C6 1.495(8) . ? N2 H2A 0.997(5) . ? N3 C8 1.491(8) . ? N3 C9 1.494(8) . ? N3 H3A 0.8600 . ? C1 C2 1.386(8) . ? C1 H1 0.9300 . ? C2 C3 1.396(9) . ? C2 H2 0.9300 . ? C3 C4 1.386(9) . ? C3 H3 0.9300 . ? C4 C5 1.381(8) . ? C4 H4 0.9300 . ? C5 C6 1.510(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.512(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.509(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 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 N2 Fe1 N1 77.36(19) . . ? N2 Fe1 N3 78.89(19) . . ? N1 Fe1 N3 83.41(19) . . ? N2 Fe1 Cl2 170.82(14) . . ? N1 Fe1 Cl2 95.14(14) . . ? N3 Fe1 Cl2 95.14(14) . . ? N2 Fe1 Cl1 89.01(14) . . ? N1 Fe1 Cl1 165.55(14) . . ? N3 Fe1 Cl1 89.33(14) . . ? Cl2 Fe1 Cl1 97.95(6) . . ? N2 Fe1 Cl3 85.94(14) . . ? N1 Fe1 Cl3 87.08(14) . . ? N3 Fe1 Cl3 163.53(14) . . ? Cl2 Fe1 Cl3 99.08(6) . . ? Cl1 Fe1 Cl3 96.84(6) . . ? C5 N1 C1 118.9(5) . . ? C5 N1 Fe1 116.7(4) . . ? C1 N1 Fe1 124.2(4) . . ? C7 N2 C6 112.3(5) . . ? C7 N2 Fe1 109.7(4) . . ? C6 N2 Fe1 111.8(3) . . ? C7 N2 H2A 105.1(4) . . ? C6 N2 H2A 106.3(5) . . ? Fe1 N2 H2A 111.3(4) . . ? C8 N3 C9 111.5(5) . . ? C8 N3 Fe1 110.1(4) . . ? C9 N3 Fe1 117.4(4) . . ? C8 N3 H3A 124.2 . . ? C9 N3 H3A 124.2 . . ? Fe1 N3 H3A 44.4 . . ? N1 C1 C2 121.5(6) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C1 C2 C3 119.1(6) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 118.7(6) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C5 C4 C3 119.3(6) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N1 C5 C4 122.3(6) . . ? N1 C5 C6 116.8(5) . . ? C4 C5 C6 120.8(6) . . ? N2 C6 C5 112.2(5) . . ? N2 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? N2 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? N2 C7 C8 109.0(5) . . ? N2 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? N2 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? N3 C8 C7 109.0(5) . . ? N3 C8 H8A 109.9 . . ? C7 C8 H8A 109.9 . . ? N3 C8 H8B 109.9 . . ? C7 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? N3 C9 C10 113.8(5) . . ? N3 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? N3 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.870 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.870 _refine_diff_density_max 0.781 _refine_diff_density_min -0.699 _refine_diff_density_rms 0.178 # Attachment '3.cif' #[Fe(L3)Cl3] data_7mpksqm _database_code_depnum_ccdc_archive 'CCDC 689798' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 Cl3 Fe N3' _chemical_formula_weight 403.53 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' Cl Cl 0.1484 0.1585 '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 7.1352(11) _cell_length_b 11.3542(18) _cell_length_c 11.6257(19) _cell_angle_alpha 82.135(3) _cell_angle_beta 85.406(3) _cell_angle_gamma 76.856(3) _cell_volume 907.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATES _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 414 _exptl_absorpt_coefficient_mu 1.271 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8225 _exptl_absorpt_correction_T_max 0.9509 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6499 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0930 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3169 _reflns_number_gt 2505 _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 ORTEP _computing_publication_material ? _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^)+(0.0488P)^2^+2.4660P] 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 3169 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0992 _refine_ls_R_factor_gt 0.0766 _refine_ls_wR_factor_ref 0.1521 _refine_ls_wR_factor_gt 0.1438 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.58521(12) 0.29972(8) 0.18804(8) 0.0087(3) Uani 1 d . . . Cl2 Cl 0.8336(2) 0.16823(15) 0.27547(14) 0.0194(4) Uani 1 d . . . Cl1 Cl 0.6494(2) 0.48152(15) 0.22449(14) 0.0167(4) Uani 1 d . . . Cl3 Cl 0.7137(2) 0.31045(13) -0.00391(13) 0.0123(4) Uani 1 d . . . N1 N 0.4459(7) 0.1587(4) 0.1493(4) 0.0113(12) Uani 1 d . . . N2 N 0.3123(7) 0.4026(4) 0.1213(4) 0.0110(11) Uani 1 d . . . N3 N 0.3932(7) 0.3012(5) 0.3507(4) 0.0130(12) Uani 1 d . . . C1 C 0.5069(9) 0.0374(6) 0.1804(5) 0.0138(14) Uani 1 d . . . H1 H 0.6145 0.0104 0.2250 0.017 Uiso 1 calc R . . C2 C 0.4175(9) -0.0470(6) 0.1492(5) 0.0157(15) Uani 1 d . . . H2 H 0.4628 -0.1296 0.1724 0.019 Uiso 1 calc R . . C3 C 0.2585(9) -0.0069(6) 0.0824(6) 0.0179(15) Uani 1 d . . . H3 H 0.1959 -0.0624 0.0589 0.021 Uiso 1 calc R . . C4 C 0.1934(9) 0.1172(6) 0.0510(5) 0.0139(14) Uani 1 d . . . H4 H 0.0850 0.1463 0.0074 0.017 Uiso 1 calc R . . C5 C 0.2917(9) 0.1969(6) 0.0851(5) 0.0131(14) Uiso 1 d . . . C6 C 0.2313(9) 0.3310(6) 0.0487(6) 0.0149(14) Uani 1 d . . . H6A H 0.2736 0.3490 -0.0319 0.018 Uiso 1 calc R . . H6B H 0.0917 0.3551 0.0542 0.018 Uiso 1 calc R . . C7 C 0.1839(9) 0.4473(6) 0.2191(5) 0.0151(15) Uani 1 d . . . H7A H 0.0528 0.4751 0.1945 0.018 Uiso 1 calc R . . H7B H 0.2236 0.5155 0.2444 0.018 Uiso 1 calc R . . C8 C 0.1928(9) 0.3466(6) 0.3173(6) 0.0181(15) Uani 1 d . . . H8A H 0.1128 0.3763 0.3833 0.022 Uiso 1 calc R . . H8B H 0.1442 0.2808 0.2937 0.022 Uiso 1 calc R . . C9 C 0.4174(10) 0.1859(6) 0.4322(6) 0.0213(16) Uani 1 d . . . H9A H 0.5470 0.1658 0.4598 0.026 Uiso 1 calc R . . H9B H 0.4037 0.1206 0.3900 0.026 Uiso 1 calc R . . C10 C 0.2745(9) 0.1923(6) 0.5361(5) 0.0159(15) Uani 1 d . . . C11 C 0.1238(11) 0.1341(6) 0.5422(6) 0.0260(17) Uani 1 d . . . H11 H 0.1113 0.0892 0.4833 0.031 Uiso 1 calc R . . C12 C -0.0094(11) 0.1424(7) 0.6361(7) 0.033(2) Uani 1 d . . . H12 H -0.1089 0.1011 0.6405 0.040 Uiso 1 calc R . . C13 C 0.0036(10) 0.2107(6) 0.7224(6) 0.0249(17) Uani 1 d . . . H13 H -0.0890 0.2185 0.7836 0.030 Uiso 1 calc R . . C14 C 0.1560(10) 0.2680(6) 0.7175(6) 0.0232(16) Uani 1 d . . . H14 H 0.1680 0.3124 0.7771 0.028 Uiso 1 calc R . . C15 C 0.2910(10) 0.2599(6) 0.6249(6) 0.0207(16) Uani 1 d . . . H15 H 0.3924 0.2995 0.6219 0.025 Uiso 1 calc R . . H2C H 0.3316 0.4857 0.0723 0.020(18) Uiso 1 d R . . H3C H 0.4317 0.3444 0.4191 0.04(2) Uiso 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 0.0029(4) 0.0118(5) 0.0113(5) -0.0001(4) 0.0004(3) -0.0028(4) Cl2 0.0089(8) 0.0267(10) 0.0206(9) 0.0057(7) -0.0026(7) -0.0041(7) Cl1 0.0149(8) 0.0198(9) 0.0187(9) -0.0072(7) 0.0003(7) -0.0081(7) Cl3 0.0113(8) 0.0123(8) 0.0128(8) -0.0022(6) 0.0022(6) -0.0018(6) N1 0.004(3) 0.007(3) 0.020(3) 0.000(2) 0.005(2) 0.001(2) N2 0.012(3) 0.008(3) 0.014(3) 0.002(2) 0.003(2) -0.007(2) N3 0.012(3) 0.023(3) 0.004(3) 0.003(2) -0.001(2) -0.007(2) C1 0.010(3) 0.019(4) 0.012(3) 0.002(3) 0.000(3) -0.006(3) C2 0.016(4) 0.012(3) 0.018(4) -0.002(3) 0.009(3) -0.006(3) C3 0.022(4) 0.016(4) 0.018(4) -0.004(3) 0.014(3) -0.013(3) C4 0.008(3) 0.023(4) 0.012(3) -0.005(3) 0.004(3) -0.006(3) C6 0.010(3) 0.015(4) 0.019(4) 0.009(3) -0.005(3) -0.008(3) C7 0.007(3) 0.019(4) 0.020(4) -0.008(3) 0.007(3) -0.005(3) C8 0.012(3) 0.028(4) 0.013(3) -0.003(3) 0.008(3) -0.005(3) C9 0.028(4) 0.021(4) 0.012(4) -0.002(3) 0.010(3) -0.003(3) C10 0.024(4) 0.013(4) 0.010(3) 0.001(3) 0.008(3) -0.007(3) C11 0.038(5) 0.026(4) 0.018(4) -0.007(3) 0.008(3) -0.017(4) C12 0.036(5) 0.037(5) 0.035(5) -0.011(4) 0.018(4) -0.026(4) C13 0.027(4) 0.025(4) 0.022(4) -0.003(3) 0.016(3) -0.009(3) C14 0.032(4) 0.023(4) 0.016(4) -0.009(3) 0.001(3) -0.006(3) C15 0.024(4) 0.023(4) 0.017(4) 0.002(3) 0.004(3) -0.014(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 2.172(5) . ? Fe1 N1 2.179(5) . ? Fe1 N3 2.244(5) . ? Fe1 Cl2 2.2525(18) . ? Fe1 Cl1 2.3131(18) . ? Fe1 Cl3 2.3419(17) . ? N1 C5 1.334(8) . ? N1 C1 1.354(8) . ? N2 C7 1.472(7) . ? N2 C6 1.479(8) . ? N2 H2C 1.0654 . ? N3 C8 1.470(8) . ? N3 C9 1.492(8) . ? N3 H3C 1.0733 . ? C1 C2 1.367(9) . ? C1 H1 0.9300 . ? C2 C3 1.381(9) . ? C2 H2 0.9300 . ? C3 C4 1.387(9) . ? C3 H3 0.9300 . ? C4 C5 1.379(9) . ? C4 H4 0.9300 . ? C5 C6 1.496(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.496(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.516(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.377(9) . ? C10 C15 1.395(9) . ? C11 C12 1.387(10) . ? C11 H11 0.9300 . ? C12 C13 1.371(10) . ? C12 H12 0.9300 . ? C13 C14 1.382(9) . ? C13 H13 0.9300 . ? C14 C15 1.385(9) . ? C14 H14 0.9300 . ? C15 H15 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 N2 Fe1 N1 76.67(18) . . ? N2 Fe1 N3 78.87(18) . . ? N1 Fe1 N3 84.58(19) . . ? N2 Fe1 Cl2 168.82(14) . . ? N1 Fe1 Cl2 94.83(14) . . ? N3 Fe1 Cl2 93.26(14) . . ? N2 Fe1 Cl1 88.27(14) . . ? N1 Fe1 Cl1 164.42(13) . . ? N3 Fe1 Cl1 88.62(14) . . ? Cl2 Fe1 Cl1 99.55(7) . . ? N2 Fe1 Cl3 87.77(14) . . ? N1 Fe1 Cl3 88.16(14) . . ? N3 Fe1 Cl3 165.95(13) . . ? Cl2 Fe1 Cl3 99.34(6) . . ? Cl1 Fe1 Cl3 95.35(6) . . ? C5 N1 C1 118.2(5) . . ? C5 N1 Fe1 116.0(4) . . ? C1 N1 Fe1 125.7(4) . . ? C7 N2 C6 114.9(5) . . ? C7 N2 Fe1 108.9(4) . . ? C6 N2 Fe1 111.1(4) . . ? C7 N2 H2C 101.5 . . ? C6 N2 H2C 110.2 . . ? Fe1 N2 H2C 109.8 . . ? C8 N3 C9 112.0(5) . . ? C8 N3 Fe1 108.1(4) . . ? C9 N3 Fe1 117.1(4) . . ? C8 N3 H3C 114.2 . . ? C9 N3 H3C 88.2 . . ? Fe1 N3 H3C 116.3 . . ? N1 C1 C2 122.9(6) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 118.6(6) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 119.0(6) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 119.1(6) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 122.1(6) . . ? N1 C5 C6 117.1(5) . . ? C4 C5 C6 120.7(6) . . ? N2 C6 C5 112.0(5) . . ? N2 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? N2 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? N2 C7 C8 109.3(5) . . ? N2 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N2 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? N3 C8 C7 109.5(5) . . ? N3 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? N3 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? N3 C9 C10 113.8(5) . . ? N3 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? N3 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C15 119.3(6) . . ? C11 C10 C9 120.2(6) . . ? C15 C10 C9 120.4(6) . . ? C10 C11 C12 120.2(7) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.8(7) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.2(6) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C15 120.7(6) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 119.8(6) . . ? C14 C15 H15 120.1 . . ? C10 C15 H15 120.1 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.840 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.127 # Attachment '7.cif' data_22mptdm _database_code_depnum_ccdc_archive 'CCDC 689799' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H23 Cl3 Fe N3' _chemical_formula_weight 431.58 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 12.1993(10) _cell_length_b 7.1387(6) _cell_length_c 21.8256(18) _cell_angle_alpha 90.00 _cell_angle_beta 92.1860(10) _cell_angle_gamma 90.00 _cell_volume 1899.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 892 _exptl_absorpt_coefficient_mu 1.220 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6890 _exptl_absorpt_correction_T_max 0.9087 _exptl_absorpt_process_details BRUKER-SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10980 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 28.24 _reflns_number_total 4409 _reflns_number_gt 3915 _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 ORTEP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0398P)^2^+1.8257P] 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 4409 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.27174(3) 0.51986(5) 0.099791(16) 0.01007(11) Uani 1 d . . . Cl3 Cl 0.14226(5) 0.28850(9) 0.07621(3) 0.01482(14) Uani 1 d . . . Cl2 Cl 0.30168(5) 0.45331(10) 0.20013(3) 0.01815(15) Uani 1 d . . . Cl1 Cl 0.41189(5) 0.35289(9) 0.05885(3) 0.01420(14) Uani 1 d . . . C15 C 0.1975(2) 0.7984(4) -0.22556(12) 0.0195(6) Uani 1 d . . . H15 H 0.1826 0.8480 -0.2644 0.023 Uiso 1 calc R . . N2 N 0.23320(17) 0.6726(3) 0.00875(9) 0.0108(4) Uani 1 d . . . N3 N 0.38452(17) 0.7724(3) 0.11088(10) 0.0130(4) Uani 1 d . . . N1 N 0.12998(17) 0.6981(3) 0.11571(9) 0.0114(4) Uani 1 d . . . C5 C 0.0694(2) 0.7488(4) 0.06580(11) 0.0120(5) Uani 1 d . . . C17 C 0.1401(2) 0.6239(4) -0.13799(12) 0.0148(5) Uani 1 d . . . H17 H 0.0862 0.5562 -0.1187 0.018 Uiso 1 calc R . . C16 C 0.1177(2) 0.6986(4) -0.19612(12) 0.0167(6) Uani 1 d . . . H16 H 0.0490 0.6814 -0.2152 0.020 Uiso 1 calc R . . C10 C 0.3413(2) 0.9223(4) 0.15058(12) 0.0160(5) Uani 1 d . . . H10A H 0.3933 1.0231 0.1537 0.024 Uiso 1 calc R . . H10B H 0.3296 0.8725 0.1907 0.024 Uiso 1 calc R . . H10C H 0.2731 0.9680 0.1330 0.024 Uiso 1 calc R . . C13 C 0.3215(2) 0.7505(4) -0.13892(12) 0.0147(5) Uani 1 d . . . H13 H 0.3904 0.7691 -0.1201 0.018 Uiso 1 calc R . . C4 C -0.0309(2) 0.8385(4) 0.07036(12) 0.0136(5) Uani 1 d . . . H4 H -0.0720 0.8702 0.0351 0.016 Uiso 1 calc R . . C6 C 0.11271(19) 0.6949(4) 0.00456(11) 0.0120(5) Uani 1 d . . . H6A H 0.0792 0.5781 -0.0091 0.014 Uiso 1 calc R . . H6B H 0.0933 0.7907 -0.0254 0.014 Uiso 1 calc R . . C2 C -0.0056(2) 0.8311(4) 0.17889(12) 0.0162(5) Uani 1 d . . . H2 H -0.0289 0.8596 0.2179 0.019 Uiso 1 calc R . . C1 C 0.0922(2) 0.7397(4) 0.17154(12) 0.0146(5) Uani 1 d . . . H1 H 0.1340 0.7053 0.2063 0.017 Uiso 1 calc R . . C11 C 0.2702(2) 0.5652(4) -0.04602(11) 0.0116(5) Uani 1 d . . . H11A H 0.2380 0.4410 -0.0448 0.014 Uiso 1 calc R . . H11B H 0.3491 0.5501 -0.0420 0.014 Uiso 1 calc R . . C12 C 0.2427(2) 0.6494(4) -0.10828(11) 0.0125(5) Uani 1 d . . . C14 C 0.2991(2) 0.8239(4) -0.19708(12) 0.0180(6) Uani 1 d . . . H14 H 0.3529 0.8906 -0.2168 0.022 Uiso 1 calc R . . C9 C 0.4947(2) 0.7218(4) 0.13703(13) 0.0188(6) Uani 1 d . . . H9A H 0.5405 0.8312 0.1386 0.028 Uiso 1 calc R . . H9B H 0.5270 0.6285 0.1117 0.028 Uiso 1 calc R . . H9C H 0.4878 0.6731 0.1777 0.028 Uiso 1 calc R . . C8 C 0.3975(2) 0.8437(4) 0.04768(12) 0.0139(5) Uani 1 d . . . H8A H 0.4440 0.7591 0.0256 0.017 Uiso 1 calc R . . H8B H 0.4328 0.9654 0.0494 0.017 Uiso 1 calc R . . C3 C -0.0691(2) 0.8803(4) 0.12726(12) 0.0166(6) Uani 1 d . . . H3 H -0.1362 0.9403 0.1311 0.020 Uiso 1 calc R . . C7 C 0.2870(2) 0.8606(4) 0.01387(11) 0.0125(5) Uani 1 d . . . H7A H 0.2405 0.9458 0.0358 0.015 Uiso 1 calc R . . H7B H 0.2969 0.9113 -0.0268 0.015 Uiso 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 0.00946(18) 0.01134(19) 0.00939(18) 0.00070(13) 0.00001(13) 0.00158(14) Cl3 0.0129(3) 0.0132(3) 0.0183(3) -0.0004(2) -0.0007(2) -0.0008(2) Cl2 0.0206(3) 0.0220(4) 0.0118(3) 0.0040(2) -0.0011(2) 0.0029(3) Cl1 0.0118(3) 0.0140(3) 0.0169(3) 0.0011(2) 0.0025(2) 0.0038(2) C15 0.0278(15) 0.0191(14) 0.0116(13) 0.0019(11) 0.0011(11) 0.0074(12) N2 0.0106(10) 0.0103(10) 0.0117(10) -0.0012(8) 0.0018(8) 0.0015(8) N3 0.0123(10) 0.0145(11) 0.0120(10) -0.0003(9) -0.0003(8) 0.0022(9) N1 0.0120(10) 0.0103(11) 0.0118(10) -0.0012(8) 0.0008(8) -0.0001(8) C5 0.0136(12) 0.0102(12) 0.0122(12) -0.0005(9) 0.0020(10) -0.0010(10) C17 0.0164(13) 0.0139(13) 0.0144(13) -0.0030(10) 0.0030(10) -0.0002(10) C16 0.0185(13) 0.0178(14) 0.0134(13) -0.0049(10) -0.0046(10) 0.0018(11) C10 0.0195(13) 0.0150(13) 0.0135(13) -0.0022(10) 0.0013(10) -0.0016(11) C13 0.0129(12) 0.0183(14) 0.0129(12) -0.0007(10) 0.0005(10) 0.0030(10) C4 0.0140(12) 0.0112(13) 0.0153(13) -0.0004(10) -0.0024(10) 0.0006(10) C6 0.0100(12) 0.0160(13) 0.0099(12) -0.0002(10) -0.0007(9) 0.0037(10) C2 0.0184(13) 0.0184(14) 0.0122(12) -0.0061(10) 0.0058(10) -0.0020(11) C1 0.0188(13) 0.0143(13) 0.0106(12) -0.0020(10) 0.0007(10) -0.0014(10) C11 0.0114(12) 0.0113(12) 0.0123(12) -0.0014(10) 0.0023(9) 0.0012(10) C12 0.0151(12) 0.0120(13) 0.0104(12) -0.0023(10) 0.0013(10) 0.0049(10) C14 0.0232(14) 0.0167(14) 0.0148(13) 0.0015(11) 0.0081(11) 0.0011(11) C9 0.0130(13) 0.0181(14) 0.0249(15) -0.0028(11) -0.0040(11) -0.0001(11) C8 0.0148(12) 0.0125(13) 0.0146(13) -0.0003(10) 0.0018(10) -0.0018(10) C3 0.0131(12) 0.0139(13) 0.0228(14) -0.0029(11) 0.0025(11) 0.0027(10) C7 0.0166(13) 0.0103(12) 0.0107(12) 0.0020(9) 0.0011(10) 0.0018(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 2.185(2) . ? Fe1 Cl2 2.2570(7) . ? Fe1 N3 2.275(2) . ? Fe1 Cl1 2.2933(7) . ? Fe1 N2 2.299(2) . ? Fe1 Cl3 2.3293(7) . ? C15 C14 1.377(4) . ? C15 C16 1.384(4) . ? C15 H15 0.9300 . ? N2 C6 1.478(3) . ? N2 C7 1.496(3) . ? N2 C11 1.504(3) . ? N3 C8 1.485(3) . ? N3 C9 1.485(3) . ? N3 C10 1.486(3) . ? N1 C5 1.342(3) . ? N1 C1 1.352(3) . ? C5 C4 1.388(4) . ? C5 C6 1.506(3) . ? C17 C16 1.394(4) . ? C17 C12 1.399(4) . ? C17 H17 0.9300 . ? C16 H16 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C13 C14 1.391(4) . ? C13 C12 1.394(4) . ? C13 H13 0.9300 . ? C4 C3 1.376(4) . ? C4 H4 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C2 C1 1.375(4) . ? C2 C3 1.388(4) . ? C2 H2 0.9300 . ? C1 H1 0.9300 . ? C11 C12 1.512(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C14 H14 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C8 C7 1.516(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C3 H3 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 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 N1 Fe1 Cl2 93.90(6) . . ? N1 Fe1 N3 90.05(8) . . ? Cl2 Fe1 N3 89.35(6) . . ? N1 Fe1 Cl1 166.12(6) . . ? Cl2 Fe1 Cl1 99.97(3) . . ? N3 Fe1 Cl1 89.79(6) . . ? N1 Fe1 N2 74.00(8) . . ? Cl2 Fe1 N2 163.44(6) . . ? N3 Fe1 N2 79.58(8) . . ? Cl1 Fe1 N2 92.33(5) . . ? N1 Fe1 Cl3 85.06(6) . . ? Cl2 Fe1 Cl3 98.54(3) . . ? N3 Fe1 Cl3 170.97(6) . . ? Cl1 Fe1 Cl3 93.14(3) . . ? N2 Fe1 Cl3 91.76(6) . . ? C14 C15 C16 119.7(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C6 N2 C7 109.94(19) . . ? C6 N2 C11 109.48(19) . . ? C7 N2 C11 111.88(19) . . ? C6 N2 Fe1 105.93(14) . . ? C7 N2 Fe1 106.62(14) . . ? C11 N2 Fe1 112.79(15) . . ? C8 N3 C9 108.3(2) . . ? C8 N3 C10 110.3(2) . . ? C9 N3 C10 106.7(2) . . ? C8 N3 Fe1 104.98(15) . . ? C9 N3 Fe1 112.54(16) . . ? C10 N3 Fe1 113.94(16) . . ? C5 N1 C1 118.5(2) . . ? C5 N1 Fe1 116.25(16) . . ? C1 N1 Fe1 124.75(17) . . ? N1 C5 C4 121.7(2) . . ? N1 C5 C6 116.8(2) . . ? C4 C5 C6 121.4(2) . . ? C16 C17 C12 120.9(2) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? C15 C16 C17 120.2(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C14 C13 C12 121.2(2) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C3 C4 C5 119.7(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N2 C6 C5 110.7(2) . . ? N2 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C1 C2 C3 119.1(2) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? N1 C1 C2 122.4(2) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? N2 C11 C12 116.6(2) . . ? N2 C11 H11A 108.1 . . ? C12 C11 H11A 108.1 . . ? N2 C11 H11B 108.1 . . ? C12 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? C13 C12 C17 117.8(2) . . ? C13 C12 C11 120.2(2) . . ? C17 C12 C11 121.9(2) . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? N3 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C8 C7 110.8(2) . . ? N3 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C4 C3 C2 118.7(2) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? N2 C7 C8 110.2(2) . . ? N2 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N2 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.869 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.869 _refine_diff_density_max 0.517 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.089