# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_a006a _database_code_depnum_ccdc_archive 'CCDC 812217' #TrackingRef 'A006A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 Cl2 Fe N6' _chemical_formula_weight 451.18 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 Orthorhombic _symmetry_space_group_name_H-M Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 15.0352(12) _cell_length_b 9.0589(7) _cell_length_c 15.3470(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2090.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1491 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 22.48 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.992 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8574 _exptl_absorpt_correction_T_max 0.9248 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 7134 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2368 _reflns_number_gt 2200 _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^)+(0.0526P)^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 0.01(3) _refine_ls_number_reflns 2368 _refine_ls_number_parameters 141 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 1.0000 0.98434(7) 0.48326(5) 0.0269(2) Uani 1 2 d S . . Cl1 Cl 1.0000 1.12587(16) 0.61168(10) 0.0474(4) Uani 1 2 d S . . Cl2 Cl 1.0000 1.18580(15) 0.37980(9) 0.0310(3) Uani 1 2 d S . . N1 N 0.8580(2) 0.9340(4) 0.4575(2) 0.0337(8) Uani 1 1 d . . . N2 N 0.8465(2) 0.8524(4) 0.3836(2) 0.0348(7) Uani 1 1 d . . . N3 N 1.0000 0.8070(5) 0.3726(4) 0.0338(11) Uani 1 2 d S . . N4 N 1.0000 0.7691(5) 0.5509(3) 0.0331(11) Uani 1 2 d S . . C1 C 0.7781(3) 0.9345(4) 0.4958(3) 0.0410(10) Uani 1 1 d . . . C2 C 0.7168(3) 0.8530(5) 0.4469(3) 0.0462(11) Uani 1 1 d . . . H2 H 0.6567 0.8362 0.4604 0.055 Uiso 1 1 calc R . . C3 C 0.7619(3) 0.8026(5) 0.3752(3) 0.0392(10) Uani 1 1 d . . . C4 C 0.7653(4) 1.0113(6) 0.5815(4) 0.0587(14) Uani 1 1 d . . . H4A H 0.8228 1.0390 0.6051 0.088 Uiso 1 1 calc R . . H4B H 0.7354 0.9455 0.6218 0.088 Uiso 1 1 calc R . . H4C H 0.7295 1.0992 0.5729 0.088 Uiso 1 1 calc R . . C5 C 0.7322(3) 0.7108(6) 0.2992(4) 0.0525(14) Uani 1 1 d . . . H5A H 0.7460 0.7621 0.2454 0.079 Uiso 1 1 calc R . . H5B H 0.6686 0.6945 0.3028 0.079 Uiso 1 1 calc R . . H5C H 0.7629 0.6166 0.3002 0.079 Uiso 1 1 calc R . . C6 C 0.9191(2) 0.8436(5) 0.3217(2) 0.0336(9) Uani 1 1 d . . . H6A H 0.9266 0.9381 0.2916 0.040 Uiso 1 1 calc R . . H6B H 0.9072 0.7668 0.2783 0.040 Uiso 1 1 calc R . . C7 C 1.0000 0.6550(7) 0.4066(4) 0.0431(15) Uani 1 2 d S . . H7A H 1.0526 0.6037 0.3841 0.052 Uiso 0.50 1 calc PR . . H7B H 0.9474 0.6037 0.3841 0.052 Uiso 0.50 1 calc PR . . C8 C 1.0000 0.6432(6) 0.5050(4) 0.0280(12) Uani 1 2 d S . . C9 C 1.0000 0.5065(6) 0.5425(4) 0.0399(14) Uani 1 2 d S . . H9 H 1.0000 0.4210 0.5078 0.048 Uiso 1 2 calc SR . . C10 C 1.0000 0.4958(8) 0.6322(5) 0.0536(18) Uani 1 2 d S . . H10 H 1.0000 0.4031 0.6598 0.064 Uiso 1 2 calc SR . . C11 C 1.0000 0.6259(7) 0.6811(4) 0.0520(18) Uani 1 2 d S . . H11 H 1.0000 0.6227 0.7423 0.062 Uiso 1 2 calc SR . . C12 C 1.0000 0.7590(8) 0.6376(4) 0.0413(15) Uani 1 2 d S . . H12 H 1.0000 0.8466 0.6704 0.050 Uiso 1 2 calc SR . . 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 0.0384(4) 0.0200(4) 0.0223(4) -0.0021(4) 0.000 0.000 Cl1 0.0932(13) 0.0242(7) 0.0248(7) -0.0041(6) 0.000 0.000 Cl2 0.0321(6) 0.0334(7) 0.0274(7) 0.0054(6) 0.000 0.000 N1 0.0374(16) 0.0371(18) 0.0266(17) -0.0047(13) 0.0079(13) -0.0048(14) N2 0.0335(16) 0.0396(19) 0.0312(16) -0.0054(15) 0.0079(16) -0.0109(14) N3 0.042(2) 0.031(3) 0.028(3) -0.002(2) 0.000 0.000 N4 0.046(3) 0.025(2) 0.028(3) -0.002(2) 0.000 0.000 C1 0.049(2) 0.039(2) 0.036(2) 0.002(2) 0.017(2) 0.0015(17) C2 0.036(2) 0.049(3) 0.053(3) 0.000(2) 0.0157(19) -0.0099(19) C3 0.0339(19) 0.040(2) 0.044(3) -0.0028(19) 0.012(2) -0.0077(18) C4 0.070(3) 0.066(3) 0.040(3) -0.010(2) 0.022(3) -0.004(3) C5 0.038(2) 0.067(4) 0.053(3) -0.015(2) 0.004(2) -0.021(2) C6 0.0248(18) 0.053(3) 0.0225(19) -0.0097(18) -0.0011(15) -0.0051(17) C7 0.061(4) 0.036(4) 0.033(4) -0.009(3) 0.000 0.000 C8 0.033(2) 0.026(3) 0.025(3) -0.004(2) 0.000 0.000 C9 0.056(4) 0.027(3) 0.037(3) -0.010(3) 0.000 0.000 C10 0.091(5) 0.024(3) 0.046(4) 0.006(3) 0.000 0.000 C11 0.103(5) 0.027(4) 0.026(3) 0.003(3) 0.000 0.000 C12 0.060(4) 0.033(3) 0.031(3) -0.008(3) 0.000 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N4 2.209(5) . ? Fe1 N1 2.219(3) . ? Fe1 N1 2.219(3) 4_755 ? Fe1 N3 2.338(5) . ? Fe1 Cl1 2.3512(16) . ? Fe1 Cl2 2.4190(15) . ? N1 C1 1.336(5) . ? N1 N2 1.364(5) . ? N2 C3 1.355(5) . ? N2 C6 1.449(5) . ? N3 C7 1.473(8) . ? N3 C6 1.483(5) . ? N3 C6 1.483(5) 4_755 ? N4 C12 1.334(7) . ? N4 C8 1.340(7) . ? C1 C2 1.399(6) . ? C1 C4 1.501(7) . ? C2 C3 1.370(6) . ? C3 C5 1.501(6) . ? C7 C8 1.514(8) . ? C8 C9 1.366(9) . ? C9 C10 1.380(10) . ? C10 C11 1.396(10) . ? C11 C12 1.379(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Fe1 N1 84.39(9) . . ? N4 Fe1 N1 84.39(9) . 4_755 ? N1 Fe1 N1 148.43(16) . 4_755 ? N4 Fe1 N3 74.6(2) . . ? N1 Fe1 N3 74.29(8) . . ? N1 Fe1 N3 74.29(8) 4_755 . ? N4 Fe1 Cl1 95.03(14) . . ? N1 Fe1 Cl1 105.16(8) . . ? N1 Fe1 Cl1 105.16(8) 4_755 . ? N3 Fe1 Cl1 169.65(14) . . ? N4 Fe1 Cl2 166.99(13) . . ? N1 Fe1 Cl2 92.18(9) . . ? N1 Fe1 Cl2 92.18(9) 4_755 . ? N3 Fe1 Cl2 92.38(14) . . ? Cl1 Fe1 Cl2 97.98(6) . . ? C1 N1 N2 104.7(3) . . ? C1 N1 Fe1 141.7(3) . . ? N2 N1 Fe1 112.4(2) . . ? C3 N2 N1 112.2(3) . . ? C3 N2 C6 128.7(4) . . ? N1 N2 C6 118.6(3) . . ? C7 N3 C6 113.3(3) . . ? C7 N3 C6 113.3(3) . 4_755 ? C6 N3 C6 110.3(5) . 4_755 ? C7 N3 Fe1 112.6(4) . . ? C6 N3 Fe1 103.2(3) . . ? C6 N3 Fe1 103.2(3) 4_755 . ? C12 N4 C8 117.7(5) . . ? C12 N4 Fe1 121.9(4) . . ? C8 N4 Fe1 120.3(4) . . ? N1 C1 C2 110.8(4) . . ? N1 C1 C4 120.1(4) . . ? C2 C1 C4 129.1(4) . . ? C3 C2 C1 106.2(4) . . ? N2 C3 C2 106.1(4) . . ? N2 C3 C5 122.5(4) . . ? C2 C3 C5 131.4(4) . . ? N2 C6 N3 106.6(3) . . ? N3 C7 C8 114.8(5) . . ? N4 C8 C9 123.4(5) . . ? N4 C8 C7 117.6(5) . . ? C9 C8 C7 119.0(5) . . ? C8 C9 C10 119.0(6) . . ? C9 C10 C11 118.4(6) . . ? C12 C11 C10 118.6(6) . . ? N4 C12 C11 122.9(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.564 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.081 # Attachment 'A242.cif' data_a242 _database_code_depnum_ccdc_archive 'CCDC 812218' #TrackingRef 'A242.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H25 Cl2 Fe N5 S' _chemical_formula_weight 470.24 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' S S 0.1246 0.1234 '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 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 12.332(3) _cell_length_b 13.092(3) _cell_length_c 13.745(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.726(5) _cell_angle_gamma 90.00 _cell_volume 2125.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 942 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.49 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 1.073 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5379 _exptl_absorpt_correction_T_max 0.7829 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 '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 14768 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4873 _reflns_number_gt 4461 _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^)+(0.0522P)^2^+1.2840P] 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 4873 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.98521(2) 0.235888(19) 0.172244(18) 0.01440(9) Uani 1 1 d . . . S1 S 1.06910(5) 0.11266(4) -0.23145(4) 0.02702(13) Uani 1 1 d . . . Cl1 Cl 1.13321(4) 0.13656(4) 0.15489(3) 0.02309(12) Uani 1 1 d . . . Cl2 Cl 1.04814(4) 0.31246(4) 0.33547(3) 0.02113(11) Uani 1 1 d . . . N1 N 0.84767(14) 0.14310(12) 0.18121(12) 0.0189(3) Uani 1 1 d . . . N2 N 0.79395(13) 0.08897(11) 0.09519(11) 0.0159(3) Uani 1 1 d . . . N5 N 0.87423(13) 0.20167(11) 0.00042(11) 0.0140(3) Uani 1 1 d . . . N4 N 0.83534(13) 0.37590(11) 0.02247(11) 0.0164(3) Uani 1 1 d . . . N3 N 0.93364(13) 0.37846(12) 0.10059(11) 0.0164(3) Uani 1 1 d . . . C1 C 0.79517(18) 0.11508(15) 0.25008(15) 0.0225(4) Uani 1 1 d . . . C2 C 0.71030(17) 0.04312(15) 0.20835(15) 0.0212(4) Uani 1 1 d . . . H2 H 0.6614 0.0115 0.2416 0.025 Uiso 1 1 calc R . . C3 C 0.71189(16) 0.02733(14) 0.10960(14) 0.0177(4) Uani 1 1 d . . . C4 C 0.8279(2) 0.1597(2) 0.35487(17) 0.0392(6) Uani 1 1 d . . . H4A H 0.8935 0.2047 0.3633 0.059 Uiso 1 1 calc R . . H4B H 0.8474 0.1045 0.4051 0.059 Uiso 1 1 calc R . . H4C H 0.7644 0.1990 0.3648 0.059 Uiso 1 1 calc R . . C5 C 0.64646(17) -0.04397(15) 0.02954(15) 0.0234(4) Uani 1 1 d . . . H5A H 0.6073 -0.0050 -0.0313 0.035 Uiso 1 1 calc R . . H5B H 0.5907 -0.0807 0.0546 0.035 Uiso 1 1 calc R . . H5C H 0.6983 -0.0930 0.0127 0.035 Uiso 1 1 calc R . . C6 C 0.83182(16) 0.09773(13) 0.00480(13) 0.0158(3) Uani 1 1 d . . . H6A H 0.7682 0.0837 -0.0565 0.019 Uiso 1 1 calc R . . H6B H 0.8927 0.0475 0.0075 0.019 Uiso 1 1 calc R . . C13 C 0.93976(15) 0.20923(14) -0.07403(13) 0.0151(3) Uani 1 1 d . . . H13A H 1.0069 0.1644 -0.0512 0.018 Uiso 1 1 calc R . . H13B H 0.9674 0.2803 -0.0736 0.018 Uiso 1 1 calc R . . C14 C 0.87521(16) 0.18046(14) -0.18396(13) 0.0182(4) Uani 1 1 d . . . H14A H 0.8463 0.1098 -0.1856 0.022 Uiso 1 1 calc R . . H14B H 0.8095 0.2266 -0.2089 0.022 Uiso 1 1 calc R . . C15 C 0.95009(16) 0.18817(14) -0.25246(13) 0.0167(4) Uani 1 1 d . . . C16 C 0.93554(18) 0.24729(14) -0.33902(15) 0.0208(4) Uani 1 1 d . . . H16 H 0.8748 0.2939 -0.3639 0.025 Uiso 1 1 calc R . . C17 C 1.02310(19) 0.22957(15) -0.38633(15) 0.0240(4) Uani 1 1 d . . . H17 H 1.0267 0.2634 -0.4465 0.029 Uiso 1 1 calc R . . C18 C 1.10014(19) 0.15990(17) -0.33699(16) 0.0270(4) Uani 1 1 d . . . H18 H 1.1638 0.1395 -0.3581 0.032 Uiso 1 1 calc R . . C12 C 0.78359(16) 0.27798(13) -0.01609(14) 0.0162(4) Uani 1 1 d . . . H12A H 0.7433 0.2835 -0.0894 0.019 Uiso 1 1 calc R . . H12B H 0.7283 0.2577 0.0202 0.019 Uiso 1 1 calc R . . C9 C 0.79745(17) 0.47030(14) -0.00856(14) 0.0186(4) Uani 1 1 d . . . C8 C 0.87604(17) 0.53731(14) 0.04955(14) 0.0201(4) Uani 1 1 d . . . H8 H 0.8740 0.6097 0.0452 0.024 Uiso 1 1 calc R . . C7 C 0.95935(17) 0.47788(14) 0.11613(14) 0.0179(4) Uani 1 1 d . . . C11 C 0.68791(19) 0.48802(16) -0.08895(16) 0.0265(4) Uani 1 1 d . . . H11A H 0.6918 0.4577 -0.1530 0.040 Uiso 1 1 calc R . . H11B H 0.6742 0.5616 -0.0981 0.040 Uiso 1 1 calc R . . H11C H 0.6260 0.4563 -0.0683 0.040 Uiso 1 1 calc R . . C10 C 1.06494(18) 0.51290(15) 0.19413(15) 0.0236(4) Uani 1 1 d . . . H10A H 1.0471 0.5303 0.2571 0.035 Uiso 1 1 calc R . . H10B H 1.0953 0.5732 0.1687 0.035 Uiso 1 1 calc R . . H10C H 1.1214 0.4580 0.2075 0.035 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 0.01470(15) 0.01426(14) 0.01344(14) 0.00033(9) 0.00278(10) 0.00044(9) S1 0.0276(3) 0.0332(3) 0.0236(2) 0.0103(2) 0.0128(2) 0.0091(2) Cl1 0.0208(2) 0.0270(2) 0.0205(2) -0.00090(17) 0.00433(18) 0.00736(17) Cl2 0.0222(2) 0.0247(2) 0.0143(2) -0.00205(16) 0.00174(17) 0.00121(17) N1 0.0241(8) 0.0187(8) 0.0147(7) -0.0027(6) 0.0070(6) -0.0042(6) N2 0.0181(8) 0.0162(7) 0.0140(7) -0.0015(6) 0.0057(6) -0.0022(6) N5 0.0162(7) 0.0118(7) 0.0146(7) 0.0001(5) 0.0052(6) 0.0003(5) N4 0.0185(8) 0.0148(7) 0.0152(7) -0.0010(6) 0.0035(6) 0.0018(6) N3 0.0187(8) 0.0169(7) 0.0126(7) -0.0011(6) 0.0028(6) -0.0009(6) C1 0.0271(10) 0.0236(10) 0.0189(9) -0.0004(7) 0.0100(8) -0.0036(8) C2 0.0232(10) 0.0211(9) 0.0224(9) 0.0022(7) 0.0116(8) -0.0017(7) C3 0.0172(9) 0.0148(8) 0.0213(9) 0.0023(7) 0.0057(7) 0.0007(7) C4 0.0541(16) 0.0481(14) 0.0225(11) -0.0110(10) 0.0221(11) -0.0255(12) C5 0.0239(10) 0.0224(10) 0.0235(9) -0.0010(8) 0.0063(8) -0.0067(8) C6 0.0200(9) 0.0141(8) 0.0152(8) -0.0005(6) 0.0079(7) -0.0012(7) C13 0.0166(8) 0.0156(8) 0.0136(8) 0.0003(6) 0.0050(7) -0.0013(6) C14 0.0183(9) 0.0218(9) 0.0142(8) -0.0006(7) 0.0042(7) -0.0010(7) C15 0.0197(9) 0.0165(8) 0.0135(8) -0.0008(6) 0.0040(7) -0.0004(7) C16 0.0288(11) 0.0153(9) 0.0204(9) -0.0015(7) 0.0105(8) -0.0015(7) C17 0.0334(11) 0.0227(10) 0.0175(9) 0.0031(7) 0.0101(8) -0.0024(8) C18 0.0318(11) 0.0327(11) 0.0220(10) 0.0041(8) 0.0166(9) 0.0019(9) C12 0.0163(9) 0.0141(8) 0.0177(8) -0.0023(6) 0.0042(7) 0.0013(6) C9 0.0241(9) 0.0165(8) 0.0164(8) 0.0008(7) 0.0077(7) 0.0042(7) C8 0.0275(10) 0.0139(8) 0.0204(9) -0.0006(7) 0.0090(8) 0.0006(7) C7 0.0238(10) 0.0166(8) 0.0155(8) -0.0014(7) 0.0093(7) -0.0008(7) C11 0.0300(11) 0.0222(10) 0.0230(10) 0.0019(8) 0.0004(8) 0.0084(8) C10 0.0276(10) 0.0198(9) 0.0223(9) -0.0027(7) 0.0053(8) -0.0057(8) _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 2.1185(17) . ? Fe1 N3 2.1209(16) . ? Fe1 Cl1 2.3086(6) . ? Fe1 Cl2 2.3747(6) . ? Fe1 N5 2.4064(15) . ? S1 C18 1.718(2) . ? S1 C15 1.7235(19) . ? N1 C1 1.343(3) . ? N1 N2 1.374(2) . ? N2 C3 1.353(2) . ? N2 C6 1.452(2) . ? N5 C6 1.465(2) . ? N5 C12 1.467(2) . ? N5 C13 1.479(2) . ? N4 C9 1.346(2) . ? N4 N3 1.369(2) . ? N4 C12 1.462(2) . ? N3 C7 1.342(2) . ? C1 C2 1.402(3) . ? C1 C4 1.498(3) . ? C2 C3 1.379(3) . ? C3 C5 1.491(3) . ? C13 C14 1.538(2) . ? C14 C15 1.500(3) . ? C15 C16 1.387(3) . ? C16 C17 1.431(3) . ? C17 C18 1.350(3) . ? C9 C8 1.379(3) . ? C9 C11 1.497(3) . ? C8 C7 1.399(3) . ? C7 C10 1.500(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N3 113.18(6) . . ? N1 Fe1 Cl1 110.67(5) . . ? N3 Fe1 Cl1 126.02(5) . . ? N1 Fe1 Cl2 103.68(4) . . ? N3 Fe1 Cl2 92.29(4) . . ? Cl1 Fe1 Cl2 106.40(2) . . ? N1 Fe1 N5 73.24(6) . . ? N3 Fe1 N5 72.43(6) . . ? Cl1 Fe1 N5 92.12(4) . . ? Cl2 Fe1 N5 160.87(4) . . ? C18 S1 C15 92.18(10) . . ? C1 N1 N2 104.77(15) . . ? C1 N1 Fe1 138.97(13) . . ? N2 N1 Fe1 116.19(11) . . ? C3 N2 N1 112.17(15) . . ? C3 N2 C6 127.65(15) . . ? N1 N2 C6 120.09(14) . . ? C6 N5 C12 111.94(14) . . ? C6 N5 C13 111.30(13) . . ? C12 N5 C13 113.02(14) . . ? C6 N5 Fe1 103.97(10) . . ? C12 N5 Fe1 102.58(10) . . ? C13 N5 Fe1 113.40(11) . . ? C9 N4 N3 111.97(15) . . ? C9 N4 C12 127.92(15) . . ? N3 N4 C12 120.10(14) . . ? C7 N3 N4 105.31(15) . . ? C7 N3 Fe1 138.94(13) . . ? N4 N3 Fe1 114.97(11) . . ? N1 C1 C2 110.47(17) . . ? N1 C1 C4 121.34(18) . . ? C2 C1 C4 128.19(19) . . ? C3 C2 C1 106.44(17) . . ? N2 C3 C2 106.14(16) . . ? N2 C3 C5 122.29(17) . . ? C2 C3 C5 131.50(17) . . ? N2 C6 N5 108.36(14) . . ? N5 C13 C14 115.60(15) . . ? C15 C14 C13 111.23(15) . . ? C16 C15 C14 128.67(18) . . ? C16 C15 S1 110.95(15) . . ? C14 C15 S1 120.31(13) . . ? C15 C16 C17 111.79(18) . . ? C18 C17 C16 113.27(18) . . ? C17 C18 S1 111.81(16) . . ? N4 C12 N5 107.90(14) . . ? N4 C9 C8 106.17(16) . . ? N4 C9 C11 122.23(17) . . ? C8 C9 C11 131.57(18) . . ? C9 C8 C7 106.65(16) . . ? N3 C7 C8 109.86(17) . . ? N3 C7 C10 121.79(17) . . ? C8 C7 C10 128.34(17) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.567 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.084 # Attachment 'A515.cif' data_a515 _database_code_depnum_ccdc_archive 'CCDC 812219' #TrackingRef 'A515.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H23 Cl2 Fe N5 O' _chemical_formula_weight 440.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 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 12.1824(7) _cell_length_b 11.6171(6) _cell_length_c 14.4312(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.3070(10) _cell_angle_gamma 90.00 _cell_volume 2030.00(19) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3325 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 26.10 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 1.022 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7915 _exptl_absorpt_correction_T_max 0.8701 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 14005 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4642 _reflns_number_gt 3877 _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^)+(0.0526P)^2^+0.5813P] 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 4642 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.80979(2) 0.63231(3) 0.17845(2) 0.02479(11) Uani 1 1 d . . . O1 O 0.25347(14) 0.62384(15) 0.24046(13) 0.0428(5) Uani 1 1 d . . . Cl1 Cl 0.88423(5) 0.48365(5) 0.10752(5) 0.04258(18) Uani 1 1 d . . . Cl2 Cl 0.91091(6) 0.79517(6) 0.20441(5) 0.04738(19) Uani 1 1 d . . . N1 N 0.66804(15) 0.66124(15) 0.08657(12) 0.0246(4) Uani 1 1 d . . . N2 N 0.56240(15) 0.62557(15) 0.09539(12) 0.0244(4) Uani 1 1 d . . . N3 N 0.76280(15) 0.60034(16) 0.31206(13) 0.0274(4) Uani 1 1 d . . . N4 N 0.67733(15) 0.65173(16) 0.35084(13) 0.0270(4) Uani 1 1 d . . . N5 N 0.50233(15) 0.63985(16) 0.24714(13) 0.0257(4) Uani 1 1 d . . . C1 C 0.6629(2) 0.7127(2) 0.00323(16) 0.0303(5) Uani 1 1 d . . . C2 C 0.5547(2) 0.7108(2) -0.04028(17) 0.0345(6) Uani 1 1 d . . . H2 H 0.5296 0.7413 -0.0991 0.041 Uiso 1 1 calc R . . C3 C 0.49214(19) 0.65559(19) 0.01980(16) 0.0289(5) Uani 1 1 d . . . C4 C 0.7642(2) 0.7610(2) -0.03180(18) 0.0442(7) Uani 1 1 d . . . H4A H 0.7932 0.8228 0.0089 0.066 Uiso 1 1 calc R . . H4B H 0.7457 0.7906 -0.0944 0.066 Uiso 1 1 calc R . . H4C H 0.8194 0.7009 -0.0326 0.066 Uiso 1 1 calc R . . C5 C 0.3716(2) 0.6294(2) 0.01333(19) 0.0399(6) Uani 1 1 d . . . H5A H 0.3613 0.5478 0.0239 0.060 Uiso 1 1 calc R . . H5B H 0.3370 0.6499 -0.0482 0.060 Uiso 1 1 calc R . . H5C H 0.3383 0.6733 0.0601 0.060 Uiso 1 1 calc R . . C6 C 0.53811(17) 0.56219(18) 0.17688(15) 0.0237(4) Uani 1 1 d . . . H6A H 0.6042 0.5204 0.2031 0.028 Uiso 1 1 calc R . . H6B H 0.4799 0.5057 0.1590 0.028 Uiso 1 1 calc R . . C7 C 0.58957(18) 0.71150(19) 0.29193(16) 0.0278(5) Uani 1 1 d . . . H7A H 0.5563 0.7686 0.3303 0.033 Uiso 1 1 calc R . . H7B H 0.6233 0.7535 0.2434 0.033 Uiso 1 1 calc R . . C8 C 0.8255(2) 0.5506(2) 0.38344(17) 0.0337(5) Uani 1 1 d . . . C9 C 0.7801(2) 0.5700(2) 0.46611(17) 0.0389(6) Uani 1 1 d . . . H9 H 0.8082 0.5440 0.5257 0.047 Uiso 1 1 calc R . . C10 C 0.6867(2) 0.6343(2) 0.44444(16) 0.0342(5) Uani 1 1 d . . . C11 C 0.9288(2) 0.4868(2) 0.3684(2) 0.0463(7) Uani 1 1 d . . . H11A H 0.9298 0.4716 0.3024 0.069 Uiso 1 1 calc R . . H11B H 0.9310 0.4145 0.4022 0.069 Uiso 1 1 calc R . . H11C H 0.9926 0.5329 0.3909 0.069 Uiso 1 1 calc R . . C12 C 0.6093(2) 0.6851(3) 0.50674(18) 0.0475(7) Uani 1 1 d . . . H12A H 0.5929 0.7641 0.4884 0.071 Uiso 1 1 calc R . . H12B H 0.6432 0.6834 0.5708 0.071 Uiso 1 1 calc R . . H12C H 0.5414 0.6407 0.5016 0.071 Uiso 1 1 calc R . . C13 C 0.43847(18) 0.5796(2) 0.31270(16) 0.0310(5) Uani 1 1 d . . . H13A H 0.4271 0.6313 0.3644 0.037 Uiso 1 1 calc R . . H13B H 0.4808 0.5130 0.3386 0.037 Uiso 1 1 calc R . . C14 C 0.32915(18) 0.5395(2) 0.26792(16) 0.0306(5) Uani 1 1 d . . . C15 C 0.2849(2) 0.4356(2) 0.2491(2) 0.0430(6) Uani 1 1 d . . . H15 H 0.3197 0.3640 0.2605 0.052 Uiso 1 1 calc R . . C16 C 0.1742(2) 0.4550(3) 0.2081(2) 0.0542(8) Uani 1 1 d . . . H16 H 0.1217 0.3985 0.1879 0.065 Uiso 1 1 calc R . . C17 C 0.1599(2) 0.5680(3) 0.2042(2) 0.0511(8) Uani 1 1 d . . . H17 H 0.0942 0.6047 0.1797 0.061 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 0.02051(17) 0.02777(19) 0.02541(18) -0.00077(13) -0.00059(12) -0.00292(12) O1 0.0254(9) 0.0483(11) 0.0541(12) -0.0049(9) 0.0012(8) 0.0029(8) Cl1 0.0384(3) 0.0386(3) 0.0488(4) -0.0104(3) -0.0042(3) 0.0096(3) Cl2 0.0541(4) 0.0410(4) 0.0465(4) -0.0078(3) 0.0031(3) -0.0219(3) N1 0.0220(9) 0.0296(10) 0.0220(9) 0.0012(7) 0.0013(7) -0.0024(7) N2 0.0217(9) 0.0280(9) 0.0228(9) 0.0001(7) -0.0004(7) 0.0004(7) N3 0.0247(10) 0.0311(10) 0.0251(10) 0.0006(8) -0.0025(8) -0.0034(8) N4 0.0260(10) 0.0326(10) 0.0221(9) 0.0008(8) 0.0012(7) -0.0033(8) N5 0.0227(9) 0.0306(10) 0.0240(9) -0.0039(8) 0.0035(7) 0.0003(7) C1 0.0367(13) 0.0319(12) 0.0227(11) 0.0023(9) 0.0049(9) -0.0007(10) C2 0.0433(14) 0.0342(13) 0.0239(12) 0.0051(10) -0.0066(10) 0.0051(11) C3 0.0280(12) 0.0289(12) 0.0279(12) -0.0057(9) -0.0059(9) 0.0078(9) C4 0.0507(17) 0.0514(16) 0.0317(14) 0.0090(12) 0.0097(12) -0.0093(13) C5 0.0271(13) 0.0463(15) 0.0433(15) -0.0053(12) -0.0098(11) 0.0064(11) C6 0.0196(10) 0.0263(11) 0.0249(11) -0.0002(9) 0.0013(8) -0.0001(8) C7 0.0296(12) 0.0272(11) 0.0263(11) -0.0018(9) 0.0017(9) -0.0009(9) C8 0.0334(13) 0.0357(13) 0.0294(12) 0.0045(10) -0.0078(10) -0.0045(10) C9 0.0453(15) 0.0459(15) 0.0232(12) 0.0083(11) -0.0076(11) -0.0075(12) C10 0.0385(14) 0.0412(14) 0.0218(11) 0.0016(10) -0.0008(10) -0.0118(11) C11 0.0421(16) 0.0511(16) 0.0425(16) 0.0045(13) -0.0100(13) 0.0082(13) C12 0.0468(16) 0.0693(19) 0.0268(13) -0.0003(13) 0.0057(12) -0.0051(14) C13 0.0243(11) 0.0435(13) 0.0257(11) -0.0014(10) 0.0043(9) -0.0003(10) C14 0.0234(11) 0.0436(14) 0.0259(12) -0.0026(10) 0.0081(9) 0.0028(10) C15 0.0354(14) 0.0425(15) 0.0517(17) -0.0046(13) 0.0076(12) -0.0043(12) C16 0.0304(14) 0.068(2) 0.065(2) -0.0191(16) 0.0056(14) -0.0173(14) C17 0.0208(13) 0.077(2) 0.0549(18) -0.0082(16) 0.0002(12) 0.0002(13) _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 2.0856(18) . ? Fe1 N3 2.1038(19) . ? Fe1 Cl1 2.2486(7) . ? Fe1 Cl2 2.2663(7) . ? O1 C17 1.365(3) . ? O1 C14 1.373(3) . ? N1 C1 1.338(3) . ? N1 N2 1.371(2) . ? N2 C3 1.356(3) . ? N2 C6 1.445(3) . ? N3 C8 1.344(3) . ? N3 N4 1.372(3) . ? N4 C10 1.358(3) . ? N4 C7 1.466(3) . ? N5 C7 1.446(3) . ? N5 C6 1.459(3) . ? N5 C13 1.467(3) . ? C1 C2 1.397(3) . ? C1 C4 1.493(3) . ? C2 C3 1.374(4) . ? C3 C5 1.492(3) . ? C8 C9 1.387(4) . ? C8 C11 1.497(4) . ? C9 C10 1.368(4) . ? C10 C12 1.494(4) . ? C13 C14 1.489(3) . ? C14 C15 1.338(4) . ? C15 C16 1.429(4) . ? C16 C17 1.325(5) . ? 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 N3 108.75(7) . . ? N1 Fe1 Cl1 100.46(5) . . ? N3 Fe1 Cl1 116.46(6) . . ? N1 Fe1 Cl2 111.57(5) . . ? N3 Fe1 Cl2 101.16(5) . . ? Cl1 Fe1 Cl2 118.51(3) . . ? C17 O1 C14 106.1(2) . . ? C1 N1 N2 105.46(17) . . ? C1 N1 Fe1 126.66(15) . . ? N2 N1 Fe1 127.76(13) . . ? C3 N2 N1 111.32(18) . . ? C3 N2 C6 128.16(19) . . ? N1 N2 C6 120.50(16) . . ? C8 N3 N4 105.51(19) . . ? C8 N3 Fe1 126.12(17) . . ? N4 N3 Fe1 126.32(14) . . ? C10 N4 N3 110.86(19) . . ? C10 N4 C7 128.6(2) . . ? N3 N4 C7 120.50(18) . . ? C7 N5 C6 113.93(17) . . ? C7 N5 C13 113.73(18) . . ? C6 N5 C13 111.90(18) . . ? N1 C1 C2 110.2(2) . . ? N1 C1 C4 120.9(2) . . ? C2 C1 C4 128.9(2) . . ? C3 C2 C1 106.6(2) . . ? N2 C3 C2 106.4(2) . . ? N2 C3 C5 121.8(2) . . ? C2 C3 C5 131.7(2) . . ? N2 C6 N5 110.73(17) . . ? N5 C7 N4 116.12(18) . . ? N3 C8 C9 110.0(2) . . ? N3 C8 C11 121.2(2) . . ? C9 C8 C11 128.8(2) . . ? C10 C9 C8 107.0(2) . . ? N4 C10 C9 106.6(2) . . ? N4 C10 C12 123.4(2) . . ? C9 C10 C12 130.0(2) . . ? N5 C13 C14 112.42(19) . . ? C15 C14 O1 110.0(2) . . ? C15 C14 C13 133.7(2) . . ? O1 C14 C13 116.3(2) . . ? C14 C15 C16 106.4(3) . . ? C17 C16 C15 106.7(2) . . ? C16 C17 O1 110.7(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.489 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.068