# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Mandon, Dominique' _publ_contact_author_email mandon@chimie.u-strasbg.fr _publ_section_title ; Tuning the Conversion of Cyclohexane into Cyclohexanol/one by Molecular Dioxygen, Protons and Reducing Agents at a Single Non-Porphyrinic Iron Centre, and Chemical Versatility of the tris(2-pyridylmethyl)amine TPAFeIICl2 Complex in Mild Oxidation Chemistry ; _publ_author_name D.Mandon # Attachment '- Formatted cifs for submission.txt' data_Cl1TPAFeCl2 _database_code_depnum_ccdc_archive 'CCDC 751029' #TrackingRef '- Formatted cifs for submission.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 Cl3 Fe N4, C H2 Cl2' _chemical_formula_sum 'C19 H19 Cl5 Fe N4' _chemical_formula_weight 536.48 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.2750(4) _cell_length_b 13.5295(5) _cell_length_c 16.2447(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.919(2) _cell_angle_gamma 90.00 _cell_volume 2249.95(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9811 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.278 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.60332 _exptl_absorpt_correction_T_max 0.68183 _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _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 19365 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 30.03 _reflns_number_total 6556 _reflns_number_gt 4551 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _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^)+(0.0754P)^2^+0.4115P] 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 6556 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1437 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 C1 C 0.5458(3) 0.3636(2) 0.80326(16) 0.0311(6) Uani 1 1 d . . . H1A H 0.5464 0.2905 0.8024 0.037 Uiso 1 1 calc R . . H1B H 0.4551 0.3862 0.7888 0.037 Uiso 1 1 calc R . . C2 C 0.5926(3) 0.3999(2) 0.88781(17) 0.0289(6) Uani 1 1 d . . . C3 C 0.5761(3) 0.3454(2) 0.95822(18) 0.0384(7) Uani 1 1 d . . . H3 H 0.5380 0.2814 0.9539 0.046 Uiso 1 1 calc R . . C4 C 0.6155(3) 0.3848(3) 1.03489(18) 0.0428(8) Uani 1 1 d . . . H4 H 0.6039 0.3488 1.0839 0.051 Uiso 1 1 calc R . . C5 C 0.6717(3) 0.4769(3) 1.03881(17) 0.0408(7) Uani 1 1 d . . . H5 H 0.7011 0.5049 1.0908 0.049 Uiso 1 1 calc R . . C6 C 0.6854(3) 0.5289(2) 0.96643(16) 0.0314(6) Uani 1 1 d . . . H6 H 0.7235 0.5929 0.9696 0.038 Uiso 1 1 calc R . . C7 C 0.7615(3) 0.3531(2) 0.75134(18) 0.0317(6) Uani 1 1 d . . . H7A H 0.7633 0.3009 0.7087 0.038 Uiso 1 1 calc R . . H7B H 0.7722 0.3205 0.8061 0.038 Uiso 1 1 calc R . . C8 C 0.8755(3) 0.4220(2) 0.74369(15) 0.0269(5) Uani 1 1 d . . . C9 C 0.9969(3) 0.3857(2) 0.72704(18) 0.0363(7) Uani 1 1 d . . . H9 H 1.0077 0.3176 0.7154 0.044 Uiso 1 1 calc R . . C10 C 1.1026(3) 0.4500(3) 0.7275(2) 0.0422(7) Uani 1 1 d . . . H10 H 1.1867 0.4265 0.7170 0.051 Uiso 1 1 calc R . . C11 C 1.0826(3) 0.5480(2) 0.7436(2) 0.0410(7) Uani 1 1 d . . . H11 H 1.1529 0.5936 0.7444 0.049 Uiso 1 1 calc R . . C12 C 0.9594(3) 0.5795(2) 0.75868(18) 0.0330(6) Uani 1 1 d . . . H12 H 0.9462 0.6478 0.7687 0.040 Uiso 1 1 calc R . . C13 C 0.5689(3) 0.3934(2) 0.65732(16) 0.0329(6) Uani 1 1 d . . . H13A H 0.4750 0.4098 0.6575 0.039 Uiso 1 1 calc R . . H13B H 0.5758 0.3242 0.6383 0.039 Uiso 1 1 calc R . . C14 C 0.6308(3) 0.4612(2) 0.59840(16) 0.0289(6) Uani 1 1 d . . . C15 C 0.6504(3) 0.4320(2) 0.51957(18) 0.0381(7) Uani 1 1 d . . . H15 H 0.6300 0.3665 0.5017 0.046 Uiso 1 1 calc R . . C16 C 0.7004(3) 0.4996(3) 0.46627(18) 0.0449(8) Uani 1 1 d . . . H16 H 0.7135 0.4813 0.4111 0.054 Uiso 1 1 calc R . . C17 C 0.7307(3) 0.5928(3) 0.49399(18) 0.0416(7) Uani 1 1 d . . . H17 H 0.7651 0.6406 0.4590 0.050 Uiso 1 1 calc R . . C18 C 0.7094(3) 0.6150(2) 0.57500(17) 0.0324(6) Uani 1 1 d . . . C19 C 0.9804(4) 0.3357(4) 1.0320(2) 0.0695(12) Uani 1 1 d . . . H19A H 1.0697 0.3318 1.0600 0.083 Uiso 1 1 calc R . . H19B H 0.9275 0.3780 1.0661 0.083 Uiso 1 1 calc R . . N1 N 0.6325(2) 0.40233(16) 0.74214(13) 0.0259(4) Uani 1 1 d . . . N2 N 0.6461(2) 0.49079(17) 0.89154(13) 0.0262(5) Uani 1 1 d . . . N3 N 0.8562(2) 0.51747(16) 0.75982(13) 0.0248(4) Uani 1 1 d . . . N4 N 0.6614(2) 0.55253(17) 0.62759(13) 0.0268(5) Uani 1 1 d . . . Cl1 Cl 0.42052(6) 0.59525(5) 0.74486(4) 0.03099(16) Uani 1 1 d . . . Cl2 Cl 0.71650(6) 0.72139(5) 0.83025(4) 0.03104(16) Uani 1 1 d . . . Cl3 Cl 0.74859(9) 0.73165(6) 0.61274(5) 0.0474(2) Uani 1 1 d . . . Cl4 Cl 0.91403(15) 0.21978(12) 1.02619(12) 0.1184(6) Uani 1 1 d . . . Cl5 Cl 0.98789(10) 0.39066(8) 0.93540(6) 0.0634(3) Uani 1 1 d . . . Fe1 Fe 0.65405(3) 0.56687(3) 0.77065(2) 0.02140(11) 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 C1 0.0317(14) 0.0234(13) 0.0384(14) 0.0043(12) 0.0043(11) -0.0053(11) C2 0.0259(13) 0.0255(14) 0.0353(14) 0.0054(11) 0.0021(11) 0.0028(10) C3 0.0375(16) 0.0333(16) 0.0448(16) 0.0158(13) 0.0064(13) 0.0034(13) C4 0.0433(18) 0.052(2) 0.0330(15) 0.0160(14) 0.0055(13) 0.0115(15) C5 0.0357(16) 0.058(2) 0.0277(14) 0.0016(14) -0.0007(12) 0.0130(15) C6 0.0259(13) 0.0373(16) 0.0307(13) -0.0032(12) 0.0001(11) 0.0039(12) C7 0.0325(14) 0.0222(13) 0.0407(14) -0.0014(12) 0.0046(12) 0.0021(11) C8 0.0293(13) 0.0252(13) 0.0263(12) 0.0015(10) 0.0020(10) 0.0026(10) C9 0.0354(15) 0.0295(15) 0.0449(16) -0.0019(13) 0.0083(13) 0.0097(12) C10 0.0285(15) 0.049(2) 0.0507(18) 0.0025(15) 0.0108(13) 0.0106(13) C11 0.0263(14) 0.0426(18) 0.0547(18) 0.0004(15) 0.0064(13) -0.0054(13) C12 0.0241(13) 0.0301(15) 0.0447(15) -0.0018(12) 0.0023(11) -0.0020(11) C13 0.0360(15) 0.0291(15) 0.0328(14) -0.0075(12) -0.0016(11) -0.0080(12) C14 0.0263(13) 0.0307(14) 0.0286(13) -0.0033(11) -0.0036(10) -0.0011(11) C15 0.0394(16) 0.0393(18) 0.0347(15) -0.0080(13) -0.0030(12) -0.0046(13) C16 0.0485(18) 0.060(2) 0.0260(14) -0.0038(14) 0.0004(13) 0.0011(16) C17 0.0445(18) 0.051(2) 0.0290(14) 0.0120(14) 0.0007(13) -0.0029(15) C18 0.0294(14) 0.0349(16) 0.0320(14) 0.0049(12) -0.0018(11) 0.0013(11) C19 0.047(2) 0.103(4) 0.057(2) 0.020(2) -0.0090(17) 0.000(2) N1 0.0248(11) 0.0215(11) 0.0312(11) 0.0001(9) 0.0007(9) -0.0033(9) N2 0.0232(10) 0.0274(12) 0.0280(11) 0.0019(9) 0.0009(8) 0.0008(9) N3 0.0234(11) 0.0224(11) 0.0286(11) -0.0009(9) 0.0024(8) 0.0003(8) N4 0.0236(11) 0.0292(12) 0.0273(11) 0.0018(9) 0.0000(9) -0.0001(9) Cl1 0.0203(3) 0.0351(4) 0.0370(4) 0.0028(3) -0.0006(2) 0.0004(3) Cl2 0.0323(3) 0.0220(3) 0.0380(3) -0.0074(3) -0.0013(3) -0.0001(2) Cl3 0.0623(5) 0.0322(4) 0.0480(4) 0.0058(3) 0.0063(4) -0.0090(4) Cl4 0.0799(9) 0.1084(12) 0.1627(14) 0.0672(11) -0.0149(9) -0.0233(8) Cl5 0.0622(6) 0.0731(7) 0.0535(5) 0.0110(5) -0.0037(4) 0.0069(5) Fe1 0.02041(18) 0.01864(19) 0.02482(19) -0.00150(14) 0.00010(13) -0.00037(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 C1 N1 1.485(3) . ? C1 C2 1.498(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N2 1.346(4) . ? C2 C3 1.383(4) . ? C3 C4 1.383(5) . ? C3 H3 0.9500 . ? C4 C5 1.373(5) . ? C4 H4 0.9500 . ? C5 C6 1.387(4) . ? C5 H5 0.9500 . ? C6 N2 1.351(3) . ? C6 H6 0.9500 . ? C7 N1 1.480(3) . ? C7 C8 1.510(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N3 1.337(3) . ? C8 C9 1.388(4) . ? C9 C10 1.391(4) . ? C9 H9 0.9500 . ? C10 C11 1.370(5) . ? C10 H10 0.9500 . ? C11 C12 1.378(4) . ? C11 H11 0.9500 . ? C12 N3 1.353(3) . ? C12 H12 0.9500 . ? C13 N1 1.478(3) . ? C13 C14 1.505(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.352(4) . ? C14 C15 1.371(4) . ? C15 C16 1.388(5) . ? C15 H15 0.9500 . ? C16 C17 1.365(5) . ? C16 H16 0.9500 . ? C17 C18 1.386(4) . ? C17 H17 0.9500 . ? C18 N4 1.327(3) . ? C18 Cl3 1.728(3) . ? C19 Cl4 1.710(5) . ? C19 Cl5 1.744(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? N1 Fe1 2.281(2) . ? N2 Fe1 2.225(2) . ? N3 Fe1 2.203(2) . ? N4 Fe1 2.340(2) . ? Cl1 Fe1 2.4307(7) . ? Cl2 Fe1 2.3692(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 N1 C1 C2 109.5(2) . . ? N1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? N1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? N2 C2 C3 121.9(3) . . ? N2 C2 C1 116.0(2) . . ? C3 C2 C1 122.1(3) . . ? C4 C3 C2 119.5(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 118.8(3) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? N2 C6 C5 121.7(3) . . ? N2 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? N1 C7 C8 114.1(2) . . ? N1 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? N1 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? N3 C8 C9 122.0(3) . . ? N3 C8 C7 116.8(2) . . ? C9 C8 C7 121.0(3) . . ? C8 C9 C10 119.5(3) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 118.4(3) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C10 C11 C12 119.3(3) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N3 C12 C11 122.9(3) . . ? N3 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? N1 C13 C14 111.5(2) . . ? N1 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? N1 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? N4 C14 C15 122.8(3) . . ? N4 C14 C13 115.6(2) . . ? C15 C14 C13 121.5(3) . . ? C14 C15 C16 119.0(3) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C17 C16 C15 119.2(3) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 117.7(3) . . ? C16 C17 H17 121.2 . . ? C18 C17 H17 121.2 . . ? N4 C18 C17 124.8(3) . . ? N4 C18 Cl3 116.2(2) . . ? C17 C18 Cl3 119.0(2) . . ? Cl4 C19 Cl5 112.9(2) . . ? Cl4 C19 H19A 109.0 . . ? Cl5 C19 H19A 109.0 . . ? Cl4 C19 H19B 109.0 . . ? Cl5 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C13 N1 C7 112.2(2) . . ? C13 N1 C1 110.6(2) . . ? C7 N1 C1 110.9(2) . . ? C13 N1 Fe1 107.26(16) . . ? C7 N1 Fe1 110.39(16) . . ? C1 N1 Fe1 105.19(16) . . ? C2 N2 C6 118.6(2) . . ? C2 N2 Fe1 115.39(17) . . ? C6 N2 Fe1 125.99(19) . . ? C8 N3 C12 117.9(2) . . ? C8 N3 Fe1 117.73(17) . . ? C12 N3 Fe1 123.90(18) . . ? C18 N4 C14 116.4(2) . . ? C18 N4 Fe1 129.22(19) . . ? C14 N4 Fe1 113.45(17) . . ? N3 Fe1 N2 92.09(8) . . ? N3 Fe1 N1 76.33(8) . . ? N2 Fe1 N1 73.58(8) . . ? N3 Fe1 N4 77.56(8) . . ? N2 Fe1 N4 147.68(8) . . ? N1 Fe1 N4 74.23(8) . . ? N3 Fe1 Cl2 94.37(6) . . ? N2 Fe1 Cl2 94.40(6) . . ? N1 Fe1 Cl2 164.26(6) . . ? N4 Fe1 Cl2 116.64(6) . . ? N3 Fe1 Cl1 163.26(6) . . ? N2 Fe1 Cl1 96.58(6) . . ? N1 Fe1 Cl1 92.39(6) . . ? N4 Fe1 Cl1 87.57(6) . . ? Cl2 Fe1 Cl1 99.19(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 33.8(3) . . . . ? N1 C1 C2 C3 -149.3(3) . . . . ? N2 C2 C3 C4 -0.1(4) . . . . ? C1 C2 C3 C4 -176.8(3) . . . . ? C2 C3 C4 C5 -0.8(5) . . . . ? C3 C4 C5 C6 1.2(5) . . . . ? C4 C5 C6 N2 -0.7(4) . . . . ? N1 C7 C8 N3 23.6(3) . . . . ? N1 C7 C8 C9 -161.3(3) . . . . ? N3 C8 C9 C10 0.4(4) . . . . ? C7 C8 C9 C10 -174.4(3) . . . . ? C8 C9 C10 C11 -0.8(5) . . . . ? C9 C10 C11 C12 0.0(5) . . . . ? C10 C11 C12 N3 1.2(5) . . . . ? N1 C13 C14 N4 -41.2(3) . . . . ? N1 C13 C14 C15 140.7(3) . . . . ? N4 C14 C15 C16 -1.9(5) . . . . ? C13 C14 C15 C16 176.0(3) . . . . ? C14 C15 C16 C17 1.0(5) . . . . ? C15 C16 C17 C18 0.0(5) . . . . ? C16 C17 C18 N4 -0.2(5) . . . . ? C16 C17 C18 Cl3 179.1(2) . . . . ? C14 C13 N1 C7 -75.0(3) . . . . ? C14 C13 N1 C1 160.6(2) . . . . ? C14 C13 N1 Fe1 46.4(3) . . . . ? C8 C7 N1 C13 97.0(3) . . . . ? C8 C7 N1 C1 -138.7(2) . . . . ? C8 C7 N1 Fe1 -22.5(3) . . . . ? C2 C1 N1 C13 -163.3(2) . . . . ? C2 C1 N1 C7 71.5(3) . . . . ? C2 C1 N1 Fe1 -47.8(2) . . . . ? C3 C2 N2 C6 0.6(4) . . . . ? C1 C2 N2 C6 177.5(2) . . . . ? C3 C2 N2 Fe1 -177.3(2) . . . . ? C1 C2 N2 Fe1 -0.4(3) . . . . ? C5 C6 N2 C2 -0.2(4) . . . . ? C5 C6 N2 Fe1 177.4(2) . . . . ? C9 C8 N3 C12 0.7(4) . . . . ? C7 C8 N3 C12 175.7(2) . . . . ? C9 C8 N3 Fe1 173.0(2) . . . . ? C7 C8 N3 Fe1 -12.0(3) . . . . ? C11 C12 N3 C8 -1.5(4) . . . . ? C11 C12 N3 Fe1 -173.3(2) . . . . ? C17 C18 N4 C14 -0.6(4) . . . . ? Cl3 C18 N4 C14 -179.9(2) . . . . ? C17 C18 N4 Fe1 167.8(2) . . . . ? Cl3 C18 N4 Fe1 -11.5(3) . . . . ? C15 C14 N4 C18 1.6(4) . . . . ? C13 C14 N4 C18 -176.4(2) . . . . ? C15 C14 N4 Fe1 -168.6(2) . . . . ? C13 C14 N4 Fe1 13.4(3) . . . . ? C8 N3 Fe1 N2 71.96(19) . . . . ? C12 N3 Fe1 N2 -116.2(2) . . . . ? C8 N3 Fe1 N1 -0.58(18) . . . . ? C12 N3 Fe1 N1 171.2(2) . . . . ? C8 N3 Fe1 N4 -77.13(19) . . . . ? C12 N3 Fe1 N4 94.7(2) . . . . ? C8 N3 Fe1 Cl2 166.54(18) . . . . ? C12 N3 Fe1 Cl2 -21.7(2) . . . . ? C8 N3 Fe1 Cl1 -49.3(3) . . . . ? C12 N3 Fe1 Cl1 122.5(2) . . . . ? C2 N2 Fe1 N3 -95.54(19) . . . . ? C6 N2 Fe1 N3 86.8(2) . . . . ? C2 N2 Fe1 N1 -20.45(18) . . . . ? C6 N2 Fe1 N1 161.9(2) . . . . ? C2 N2 Fe1 N4 -25.8(3) . . . . ? C6 N2 Fe1 N4 156.55(19) . . . . ? C2 N2 Fe1 Cl2 169.91(18) . . . . ? C6 N2 Fe1 Cl2 -7.8(2) . . . . ? C2 N2 Fe1 Cl1 70.12(18) . . . . ? C6 N2 Fe1 Cl1 -107.6(2) . . . . ? C13 N1 Fe1 N3 -109.85(17) . . . . ? C7 N1 Fe1 N3 12.65(16) . . . . ? C1 N1 Fe1 N3 132.35(17) . . . . ? C13 N1 Fe1 N2 153.78(18) . . . . ? C7 N1 Fe1 N2 -83.71(17) . . . . ? C1 N1 Fe1 N2 35.98(16) . . . . ? C13 N1 Fe1 N4 -29.16(16) . . . . ? C7 N1 Fe1 N4 93.34(17) . . . . ? C1 N1 Fe1 N4 -146.96(18) . . . . ? C13 N1 Fe1 Cl2 -164.84(17) . . . . ? C7 N1 Fe1 Cl2 -42.3(3) . . . . ? C1 N1 Fe1 Cl2 77.4(3) . . . . ? C13 N1 Fe1 Cl1 57.63(16) . . . . ? C7 N1 Fe1 Cl1 -179.87(16) . . . . ? C1 N1 Fe1 Cl1 -60.17(16) . . . . ? C18 N4 Fe1 N3 -80.4(2) . . . . ? C14 N4 Fe1 N3 88.28(19) . . . . ? C18 N4 Fe1 N2 -154.2(2) . . . . ? C14 N4 Fe1 N2 14.5(3) . . . . ? C18 N4 Fe1 N1 -159.5(2) . . . . ? C14 N4 Fe1 N1 9.18(18) . . . . ? C18 N4 Fe1 Cl2 8.3(2) . . . . ? C14 N4 Fe1 Cl2 176.94(16) . . . . ? C18 N4 Fe1 Cl1 107.3(2) . . . . ? C14 N4 Fe1 Cl1 -84.00(18) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.939 _refine_diff_density_min -0.916 _refine_diff_density_rms 0.100 data_Cl2TPAFeCl2 _database_code_depnum_ccdc_archive 'CCDC 751030' #TrackingRef '- Formatted cifs for submission.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 Cl4 Fe N4' _chemical_formula_sum 'C18 H16 Cl4 Fe N4' _chemical_formula_weight 486.00 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 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 9.1920(5) _cell_length_b 15.5454(10) _cell_length_c 15.1189(8) _cell_angle_alpha 90.00 _cell_angle_beta 106.520(3) _cell_angle_gamma 90.00 _cell_volume 2071.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4952 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 1.255 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.60923 _exptl_absorpt_correction_T_max 0.71636 _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _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 6529 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 30.01 _reflns_number_total 4056 _reflns_number_gt 3368 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _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^)+(0.0514P)^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 -0.042(16) _refine_ls_number_reflns 4056 _refine_ls_number_parameters 244 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 C1 C 0.2954(5) 0.9640(2) 0.0263(2) 0.0408(9) Uani 1 1 d . . . H1A H 0.2310 1.0160 0.0109 0.049 Uiso 1 1 calc R . . H1B H 0.3751 0.9686 -0.0059 0.049 Uiso 1 1 calc R . . C2 C 0.3710(4) 0.9628(2) 0.1295(2) 0.0313(7) Uani 1 1 d . . . C3 C 0.4674(4) 1.0287(2) 0.1708(3) 0.0389(9) Uani 1 1 d . . . H3 H 0.4870 1.0750 0.1349 0.047 Uiso 1 1 calc R . . C4 C 0.5347(5) 1.0266(3) 0.2648(3) 0.0448(9) Uani 1 1 d . . . H4 H 0.6016 1.0712 0.2944 0.054 Uiso 1 1 calc R . . C5 C 0.5031(5) 0.9584(2) 0.3152(3) 0.0412(9) Uani 1 1 d . . . H5 H 0.5474 0.9556 0.3801 0.049 Uiso 1 1 calc R . . C6 C 0.4062(4) 0.8946(2) 0.2698(2) 0.0367(8) Uani 1 1 d . . . H6 H 0.3848 0.8478 0.3045 0.044 Uiso 1 1 calc R . . C7 C 0.0396(4) 0.9118(3) -0.0528(2) 0.0406(9) Uani 1 1 d . . . H7A H -0.0180 0.8619 -0.0859 0.049 Uiso 1 1 calc R . . H7B H 0.0353 0.9583 -0.0982 0.049 Uiso 1 1 calc R . . C8 C -0.0309(4) 0.9423(2) 0.0203(3) 0.0412(9) Uani 1 1 d . . . C9 C -0.1254(6) 1.0127(3) 0.0067(3) 0.0594(12) Uani 1 1 d . . . H9 H -0.1481 1.0439 -0.0496 0.071 Uiso 1 1 calc R . . C10 C -0.1870(7) 1.0370(3) 0.0766(4) 0.0754(16) Uani 1 1 d . . . H10 H -0.2532 1.0851 0.0687 0.090 Uiso 1 1 calc R . . C11 C -0.1514(6) 0.9912(3) 0.1568(4) 0.0669(14) Uani 1 1 d . . . H11 H -0.1913 1.0068 0.2061 0.080 Uiso 1 1 calc R . . C12 C -0.0565(5) 0.9221(3) 0.1641(3) 0.0468(10) Uani 1 1 d . . . C13 C 0.2545(4) 0.8403(3) -0.0788(2) 0.0388(8) Uani 1 1 d . . . H13A H 0.2622 0.8808 -0.1279 0.047 Uiso 1 1 calc R . . H13B H 0.1809 0.7948 -0.1076 0.047 Uiso 1 1 calc R . . C14 C 0.4067(4) 0.8005(2) -0.0354(3) 0.0347(8) Uani 1 1 d . . . C15 C 0.5152(5) 0.7944(3) -0.0822(3) 0.0480(11) Uani 1 1 d . . . H15 H 0.4939 0.8151 -0.1437 0.058 Uiso 1 1 calc R . . C16 C 0.6531(5) 0.7587(3) -0.0399(3) 0.0539(11) Uani 1 1 d . . . H16 H 0.7285 0.7540 -0.0716 0.065 Uiso 1 1 calc R . . C17 C 0.6810(5) 0.7296(3) 0.0487(3) 0.0484(10) Uani 1 1 d . . . H17 H 0.7767 0.7059 0.0808 0.058 Uiso 1 1 calc R . . C18 C 0.5648(5) 0.7359(3) 0.0903(3) 0.0456(10) Uani 1 1 d . . . N1 N 0.1996(3) 0.88664(18) -0.00978(19) 0.0327(6) Uani 1 1 d . . . N2 N 0.3411(3) 0.89620(17) 0.1783(2) 0.0324(6) Uani 1 1 d . . . N3 N 0.0051(4) 0.89562(19) 0.0989(2) 0.0368(7) Uani 1 1 d . . . N4 N 0.4289(4) 0.7690(2) 0.0507(2) 0.0387(7) Uani 1 1 d . . . Cl1 Cl 0.03650(10) 0.69863(5) -0.00394(6) 0.0344(2) Uani 1 1 d . . . Cl2 Cl 0.23581(10) 0.70213(5) 0.23202(6) 0.0345(2) Uani 1 1 d . . . Cl3 Cl -0.00733(16) 0.86480(9) 0.26669(9) 0.0701(4) Uani 1 1 d . . . Cl4 Cl 0.59797(15) 0.69891(11) 0.20156(8) 0.0813(5) Uani 1 1 d . . . Fe1 Fe 0.20048(4) 0.79387(3) 0.10569(3) 0.02863(12) 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 C1 0.050(2) 0.035(2) 0.0346(19) 0.0104(16) 0.0078(16) -0.0038(17) C2 0.0366(18) 0.0237(16) 0.0361(18) 0.0062(14) 0.0143(15) 0.0031(14) C3 0.051(2) 0.0273(17) 0.0423(19) 0.0043(17) 0.0202(18) -0.0070(17) C4 0.058(3) 0.0344(19) 0.042(2) -0.0068(18) 0.0140(19) -0.0167(19) C5 0.055(2) 0.035(2) 0.0332(18) -0.0050(16) 0.0117(17) -0.0149(18) C6 0.046(2) 0.0318(19) 0.0309(17) 0.0010(16) 0.0093(16) -0.0096(17) C7 0.047(2) 0.039(2) 0.0311(19) 0.0081(16) 0.0029(16) 0.0105(17) C8 0.042(2) 0.0316(19) 0.045(2) 0.0011(17) 0.0038(17) 0.0083(17) C9 0.066(3) 0.048(3) 0.058(3) 0.003(2) 0.008(2) 0.029(2) C10 0.077(4) 0.063(3) 0.076(3) -0.007(3) 0.007(3) 0.044(3) C11 0.066(3) 0.065(3) 0.073(3) -0.016(3) 0.026(3) 0.029(3) C12 0.048(2) 0.044(2) 0.049(2) -0.0039(19) 0.0158(19) 0.0122(19) C13 0.044(2) 0.046(2) 0.0263(16) 0.0071(16) 0.0113(15) 0.0053(18) C14 0.0380(19) 0.039(2) 0.0297(18) 0.0029(15) 0.0134(15) -0.0007(16) C15 0.053(2) 0.060(3) 0.038(2) 0.011(2) 0.025(2) 0.005(2) C16 0.045(2) 0.071(3) 0.054(2) 0.002(2) 0.027(2) 0.005(2) C17 0.035(2) 0.063(3) 0.049(2) 0.004(2) 0.0137(19) 0.0043(19) C18 0.039(2) 0.064(3) 0.0325(18) 0.010(2) 0.0082(16) 0.009(2) N1 0.0344(16) 0.0328(16) 0.0291(14) 0.0062(13) 0.0061(12) 0.0001(13) N2 0.0384(16) 0.0273(14) 0.0303(14) 0.0022(13) 0.0076(12) -0.0057(13) N3 0.0396(17) 0.0320(15) 0.0399(16) -0.0021(14) 0.0129(13) 0.0077(13) N4 0.0349(16) 0.0530(19) 0.0292(14) 0.0091(15) 0.0110(13) 0.0065(15) Cl1 0.0359(5) 0.0317(4) 0.0318(4) -0.0038(4) 0.0036(4) 0.0024(4) Cl2 0.0520(5) 0.0245(4) 0.0288(4) 0.0022(3) 0.0144(4) -0.0057(4) Cl3 0.0946(10) 0.0745(8) 0.0560(6) 0.0099(6) 0.0454(7) 0.0338(7) Cl4 0.0560(8) 0.1468(15) 0.0419(6) 0.0387(7) 0.0155(6) 0.0376(8) Fe1 0.0350(3) 0.0245(2) 0.0258(2) 0.0031(2) 0.00751(19) -0.0016(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 C1 N1 1.498(5) . ? C1 C2 1.517(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N2 1.345(4) . ? C2 C3 1.382(5) . ? C3 C4 1.379(5) . ? C3 H3 0.9500 . ? C4 C5 1.384(5) . ? C4 H4 0.9500 . ? C5 C6 1.379(5) . ? C5 H5 0.9500 . ? C6 N2 1.342(4) . ? C6 H6 0.9500 . ? C7 N1 1.481(4) . ? C7 C8 1.509(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N3 1.351(5) . ? C8 C9 1.375(6) . ? C9 C10 1.386(7) . ? C9 H9 0.9500 . ? C10 C11 1.364(7) . ? C10 H10 0.9500 . ? C11 C12 1.369(6) . ? C11 H11 0.9500 . ? C12 N3 1.334(5) . ? C12 Cl3 1.733(4) . ? C13 N1 1.470(5) . ? C13 C14 1.500(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.352(5) . ? C14 C15 1.380(5) . ? C15 C16 1.365(6) . ? C15 H15 0.9500 . ? C16 C17 1.368(6) . ? C16 H16 0.9500 . ? C17 C18 1.389(5) . ? C17 H17 0.9500 . ? C18 N4 1.326(5) . ? C18 Cl4 1.721(4) . ? N1 Fe1 2.263(3) . ? N2 Fe1 2.144(3) . ? N3 Fe1 2.373(3) . ? Cl1 Fe1 2.4063(9) . ? Cl2 Fe1 2.3312(8) . ? 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 C1 C2 114.5(3) . . ? N1 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? N1 C1 H1B 108.6 . . ? C2 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? N2 C2 C3 121.8(3) . . ? N2 C2 C1 117.9(3) . . ? C3 C2 C1 120.3(3) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 118.8(4) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C6 C5 C4 118.9(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? N2 C6 C5 122.4(3) . . ? N2 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? N1 C7 C8 109.9(3) . . ? N1 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? N1 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? N3 C8 C9 123.1(4) . . ? N3 C8 C7 115.2(3) . . ? C9 C8 C7 121.7(4) . . ? C8 C9 C10 118.7(5) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 119.3(4) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 117.9(4) . . ? C10 C11 H11 121.1 . . ? C12 C11 H11 121.1 . . ? N3 C12 C11 125.2(4) . . ? N3 C12 Cl3 116.5(3) . . ? C11 C12 Cl3 118.3(3) . . ? N1 C13 C14 110.9(3) . . ? N1 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.0 . . ? N4 C14 C15 122.4(4) . . ? N4 C14 C13 115.9(3) . . ? C15 C14 C13 121.6(3) . . ? C16 C15 C14 119.9(4) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 118.9(4) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C16 C17 C18 117.8(4) . . ? C16 C17 H17 121.1 . . ? C18 C17 H17 121.1 . . ? N4 C18 C17 124.8(4) . . ? N4 C18 Cl4 117.0(3) . . ? C17 C18 Cl4 118.2(3) . . ? C13 N1 C7 108.4(3) . . ? C13 N1 C1 111.5(3) . . ? C7 N1 C1 110.8(3) . . ? C13 N1 Fe1 108.0(2) . . ? C7 N1 Fe1 107.0(2) . . ? C1 N1 Fe1 110.97(19) . . ? C6 N2 C2 118.6(3) . . ? C6 N2 Fe1 122.8(2) . . ? C2 N2 Fe1 118.5(2) . . ? C12 N3 C8 115.8(3) . . ? C12 N3 Fe1 130.4(3) . . ? C8 N3 Fe1 112.9(2) . . ? C18 N4 C14 116.1(3) . . ? N2 Fe1 N1 77.97(11) . . ? N2 Fe1 Cl2 96.38(8) . . ? N1 Fe1 Cl2 172.38(8) . . ? N2 Fe1 N3 82.31(11) . . ? N1 Fe1 N3 72.85(11) . . ? Cl2 Fe1 N3 111.75(8) . . ? N2 Fe1 Cl1 167.76(8) . . ? N1 Fe1 Cl1 89.80(8) . . ? Cl2 Fe1 Cl1 95.85(3) . . ? N3 Fe1 Cl1 93.56(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -2.6(5) . . . . ? N1 C1 C2 C3 177.4(3) . . . . ? N2 C2 C3 C4 -0.2(6) . . . . ? C1 C2 C3 C4 179.8(4) . . . . ? C2 C3 C4 C5 -0.3(6) . . . . ? C3 C4 C5 C6 0.4(6) . . . . ? C4 C5 C6 N2 -0.1(6) . . . . ? N1 C7 C8 N3 -41.4(5) . . . . ? N1 C7 C8 C9 138.9(4) . . . . ? N3 C8 C9 C10 0.0(8) . . . . ? C7 C8 C9 C10 179.7(5) . . . . ? C8 C9 C10 C11 0.5(9) . . . . ? C9 C10 C11 C12 -0.6(9) . . . . ? C10 C11 C12 N3 0.2(8) . . . . ? C10 C11 C12 Cl3 178.6(4) . . . . ? N1 C13 C14 N4 36.6(5) . . . . ? N1 C13 C14 C15 -145.3(4) . . . . ? N4 C14 C15 C16 -2.8(7) . . . . ? C13 C14 C15 C16 179.2(4) . . . . ? C14 C15 C16 C17 -0.2(8) . . . . ? C15 C16 C17 C18 1.8(8) . . . . ? C16 C17 C18 N4 -0.8(8) . . . . ? C16 C17 C18 Cl4 179.6(4) . . . . ? C14 C13 N1 C7 -170.6(3) . . . . ? C14 C13 N1 C1 67.1(4) . . . . ? C14 C13 N1 Fe1 -55.0(3) . . . . ? C8 C7 N1 C13 168.0(3) . . . . ? C8 C7 N1 C1 -69.3(4) . . . . ? C8 C7 N1 Fe1 51.8(3) . . . . ? C2 C1 N1 C13 -120.0(3) . . . . ? C2 C1 N1 C7 119.2(3) . . . . ? C2 C1 N1 Fe1 0.5(4) . . . . ? C5 C6 N2 C2 -0.3(6) . . . . ? C5 C6 N2 Fe1 176.4(3) . . . . ? C3 C2 N2 C6 0.5(5) . . . . ? C1 C2 N2 C6 -179.5(3) . . . . ? C3 C2 N2 Fe1 -176.4(3) . . . . ? C1 C2 N2 Fe1 3.6(4) . . . . ? C11 C12 N3 C8 0.2(7) . . . . ? Cl3 C12 N3 C8 -178.2(3) . . . . ? C11 C12 N3 Fe1 168.7(4) . . . . ? Cl3 C12 N3 Fe1 -9.8(5) . . . . ? C9 C8 N3 C12 -0.3(6) . . . . ? C7 C8 N3 C12 179.9(4) . . . . ? C9 C8 N3 Fe1 -170.8(4) . . . . ? C7 C8 N3 Fe1 9.5(4) . . . . ? C17 C18 N4 C14 -1.9(7) . . . . ? Cl4 C18 N4 C14 177.7(3) . . . . ? C15 C14 N4 C18 3.7(6) . . . . ? C13 C14 N4 C18 -178.2(4) . . . . ? C6 N2 Fe1 N1 -179.3(3) . . . . ? C2 N2 Fe1 N1 -2.5(2) . . . . ? C6 N2 Fe1 Cl2 -4.4(3) . . . . ? C2 N2 Fe1 Cl2 172.3(2) . . . . ? C6 N2 Fe1 N3 106.7(3) . . . . ? C2 N2 Fe1 N3 -76.6(3) . . . . ? C6 N2 Fe1 Cl1 177.7(3) . . . . ? C2 N2 Fe1 Cl1 -5.6(6) . . . . ? C13 N1 Fe1 N2 123.4(2) . . . . ? C7 N1 Fe1 N2 -120.1(2) . . . . ? C1 N1 Fe1 N2 1.0(2) . . . . ? C13 N1 Fe1 N3 -151.0(2) . . . . ? C7 N1 Fe1 N3 -34.5(2) . . . . ? C1 N1 Fe1 N3 86.5(2) . . . . ? C13 N1 Fe1 Cl1 -57.2(2) . . . . ? C7 N1 Fe1 Cl1 59.3(2) . . . . ? C1 N1 Fe1 Cl1 -179.7(2) . . . . ? C12 N3 Fe1 N2 -74.7(4) . . . . ? C8 N3 Fe1 N2 94.1(3) . . . . ? C12 N3 Fe1 N1 -154.4(4) . . . . ? C8 N3 Fe1 N1 14.4(3) . . . . ? C12 N3 Fe1 Cl2 19.2(4) . . . . ? C8 N3 Fe1 Cl2 -172.1(2) . . . . ? C12 N3 Fe1 Cl1 116.9(4) . . . . ? C8 N3 Fe1 Cl1 -74.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.361 _refine_diff_density_min -0.506 _refine_diff_density_rms 0.068 data_Cl3TPAFeCl2 _database_code_depnum_ccdc_archive 'CCDC 751031' #TrackingRef '- Formatted cifs for submission.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H15 Cl5 Fe N4' _chemical_formula_sum 'C18 H15 Cl5 Fe N4' _chemical_formula_weight 520.44 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6446(5) _cell_length_b 11.4985(9) _cell_length_c 13.3214(9) _cell_angle_alpha 86.774(3) _cell_angle_beta 75.367(4) _cell_angle_gamma 78.051(4) _cell_volume 1253.42(15) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 18532 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 1.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72497 _exptl_absorpt_correction_T_max 0.98762 _exptl_absorpt_process_details 'MULscan in PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _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 12735 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.0792 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5716 _reflns_number_gt 4062 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _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^)+(0.1228P)^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 5716 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.1967 _refine_ls_wR_factor_gt 0.1844 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 C1 C 0.1236(5) 0.6620(4) 0.3457(3) 0.0301(9) Uani 1 1 d . . . H1A H 0.1633 0.6225 0.4050 0.036 Uiso 1 1 calc R . . H1B H 0.0168 0.6415 0.3488 0.036 Uiso 1 1 calc R . . C2 C 0.1001(5) 0.7970(4) 0.3566(3) 0.0325(9) Uani 1 1 d . . . C3 C -0.0292(6) 0.8748(4) 0.3304(4) 0.0452(11) Uani 1 1 d . . . H3 H -0.1106 0.8458 0.3085 0.054 Uiso 1 1 calc R . . C4 C -0.0368(6) 0.9956(5) 0.3369(4) 0.0533(13) Uani 1 1 d . . . H4 H -0.1233 1.0510 0.3185 0.064 Uiso 1 1 calc R . . C5 C 0.0824(7) 1.0356(4) 0.3704(4) 0.0534(13) Uani 1 1 d . . . H5 H 0.0806 1.1178 0.3761 0.064 Uiso 1 1 calc R . . C6 C 0.2026(6) 0.9497(4) 0.3949(4) 0.0444(11) Uani 1 1 d . . . C7 C 0.1784(5) 0.6578(4) 0.1550(3) 0.0315(9) Uani 1 1 d . . . H7A H 0.2685 0.6428 0.0915 0.038 Uiso 1 1 calc R . . H7B H 0.1359 0.7446 0.1607 0.038 Uiso 1 1 calc R . . C8 C 0.0449(5) 0.5965(4) 0.1463(3) 0.0327(9) Uani 1 1 d . . . C9 C -0.0847(5) 0.6531(5) 0.1070(3) 0.0405(11) Uani 1 1 d . . . H9 H -0.1001 0.7361 0.0931 0.049 Uiso 1 1 calc R . . C10 C -0.1909(5) 0.5881(5) 0.0881(4) 0.0466(13) Uani 1 1 d . . . H10 H -0.2778 0.6252 0.0583 0.056 Uiso 1 1 calc R . . C11 C -0.1706(5) 0.4682(6) 0.1128(3) 0.0478(14) Uani 1 1 d . . . H11 H -0.2441 0.4218 0.1022 0.057 Uiso 1 1 calc R . . C12 C -0.0373(5) 0.4177(4) 0.1541(3) 0.0386(10) Uani 1 1 d . . . C13 C 0.4064(5) 0.6421(4) 0.2336(3) 0.0336(9) Uani 1 1 d . . . H13A H 0.3955 0.7273 0.2484 0.040 Uiso 1 1 calc R . . H13B H 0.4698 0.6270 0.1609 0.040 Uiso 1 1 calc R . . C14 C 0.4966(5) 0.5670(4) 0.3054(3) 0.0313(9) Uani 1 1 d . . . C15 C 0.5974(5) 0.6095(4) 0.3525(3) 0.0388(11) Uani 1 1 d . . . H15 H 0.6011 0.6916 0.3500 0.047 Uiso 1 1 calc R . . C16 C 0.6962(5) 0.5266(5) 0.4050(3) 0.0417(12) Uani 1 1 d . . . H16 H 0.7688 0.5523 0.4378 0.050 Uiso 1 1 calc R . . C17 C 0.6856(5) 0.4109(5) 0.4078(3) 0.0411(11) Uani 1 1 d . . . H17 H 0.7523 0.3535 0.4410 0.049 Uiso 1 1 calc R . . C18 C 0.5759(5) 0.3782(4) 0.3615(3) 0.0336(9) Uani 1 1 d . . . N1 N 0.2419(4) 0.6150(3) 0.2465(3) 0.0284(7) Uani 1 1 d . . . N2 N 0.2141(5) 0.8345(3) 0.3905(3) 0.0371(8) Uani 1 1 d . . . N3 N 0.0683(4) 0.4790(3) 0.1717(3) 0.0331(8) Uani 1 1 d . . . N4 N 0.4820(4) 0.4517(3) 0.3121(3) 0.0297(7) Uani 1 1 d . . . Cl1 Cl 0.3568(2) 0.99539(13) 0.43589(12) 0.0651(4) Uani 1 1 d . . . Cl2 Cl -0.00102(16) 0.26780(12) 0.18070(10) 0.0509(3) Uani 1 1 d . . . Cl3 Cl 0.55633(14) 0.23052(11) 0.36792(11) 0.0498(3) Uani 1 1 d . . . Cl4 Cl 0.12615(11) 0.35324(9) 0.39935(7) 0.0289(2) Uani 1 1 d . . . Cl5 Cl 0.46052(10) 0.35164(10) 0.08988(7) 0.0294(3) Uani 1 1 d . . . Fe1 Fe 0.27590(6) 0.42191(5) 0.24842(4) 0.0279(2) 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 C1 0.031(2) 0.031(2) 0.027(2) 0.0041(17) -0.0070(16) -0.0039(16) C2 0.033(2) 0.034(2) 0.029(2) 0.0007(18) -0.0067(17) -0.0038(17) C3 0.042(3) 0.039(3) 0.052(3) -0.004(2) -0.016(2) 0.002(2) C4 0.056(3) 0.042(3) 0.051(3) -0.001(2) -0.013(3) 0.012(2) C5 0.076(4) 0.031(3) 0.049(3) -0.001(2) -0.011(3) -0.004(2) C6 0.061(3) 0.039(3) 0.040(3) 0.006(2) -0.018(2) -0.021(2) C7 0.032(2) 0.032(2) 0.026(2) 0.0062(17) -0.0039(17) -0.0040(17) C8 0.032(2) 0.038(2) 0.025(2) -0.0013(18) -0.0049(17) -0.0023(18) C9 0.036(2) 0.055(3) 0.024(2) 0.003(2) -0.0068(18) 0.004(2) C10 0.021(2) 0.082(4) 0.034(2) -0.005(2) -0.0096(18) 0.001(2) C11 0.025(2) 0.097(4) 0.026(2) -0.013(3) -0.0053(18) -0.020(2) C12 0.036(2) 0.055(3) 0.026(2) -0.004(2) -0.0045(18) -0.015(2) C13 0.032(2) 0.027(2) 0.041(2) 0.0018(18) -0.0044(18) -0.0088(17) C14 0.026(2) 0.040(3) 0.025(2) 0.0008(18) -0.0017(16) -0.0075(17) C15 0.031(2) 0.052(3) 0.035(2) -0.010(2) -0.0017(18) -0.018(2) C16 0.028(2) 0.073(4) 0.029(2) -0.001(2) -0.0095(18) -0.019(2) C17 0.023(2) 0.068(3) 0.032(2) 0.001(2) -0.0085(18) -0.006(2) C18 0.0229(19) 0.048(3) 0.028(2) 0.0036(19) -0.0061(16) -0.0029(18) N1 0.0179(15) 0.038(2) 0.0286(17) -0.0007(14) -0.0063(13) -0.0038(13) N2 0.043(2) 0.030(2) 0.037(2) -0.0044(16) -0.0103(16) -0.0051(16) N3 0.0268(17) 0.046(2) 0.0273(18) -0.0039(16) -0.0065(14) -0.0071(15) N4 0.0265(17) 0.0339(19) 0.0288(17) 0.0031(15) -0.0086(14) -0.0053(14) Cl1 0.0930(11) 0.0511(8) 0.0697(9) 0.0059(7) -0.0370(8) -0.0364(8) Cl2 0.0577(7) 0.0546(8) 0.0498(7) -0.0025(6) -0.0163(6) -0.0279(6) Cl3 0.0487(7) 0.0385(7) 0.0653(8) 0.0129(6) -0.0266(6) -0.0038(5) Cl4 0.0297(5) 0.0330(5) 0.0263(5) 0.0040(4) -0.0075(4) -0.0118(4) Cl5 0.0172(4) 0.0552(7) 0.0162(4) -0.0016(4) -0.0040(3) -0.0076(4) Fe1 0.0267(3) 0.0304(4) 0.0280(3) 0.0026(2) -0.0092(2) -0.0068(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 C1 N1 1.501(5) . ? C1 C2 1.534(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N2 1.335(5) . ? C2 C3 1.385(6) . ? C3 C4 1.384(7) . ? C3 H3 0.9500 . ? C4 C5 1.386(7) . ? C4 H4 0.9500 . ? C5 C6 1.368(7) . ? C5 H5 0.9500 . ? C6 N2 1.311(6) . ? C6 Cl1 1.743(5) . ? C7 N1 1.479(5) . ? C7 C8 1.502(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N3 1.361(6) . ? C8 C9 1.381(6) . ? C9 C10 1.374(7) . ? C9 H9 0.9500 . ? C10 C11 1.385(8) . ? C10 H10 0.9500 . ? C11 C12 1.405(6) . ? C11 H11 0.9500 . ? C12 N3 1.333(5) . ? C12 Cl2 1.720(5) . ? C13 N1 1.484(5) . ? C13 C14 1.508(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.353(5) . ? C14 C15 1.370(6) . ? C15 C16 1.420(7) . ? C15 H15 0.9500 . ? C16 C17 1.350(7) . ? C16 H16 0.9500 . ? C17 C18 1.375(6) . ? C17 H17 0.9500 . ? C18 N4 1.316(5) . ? C18 Cl3 1.736(5) . ? N1 Fe1 2.178(4) . ? N3 Fe1 2.250(3) . ? N4 Fe1 2.249(3) . ? Cl4 Fe1 2.2959(11) . ? Cl5 Fe1 2.3697(10) . ? 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 C1 C2 113.1(3) . . ? N1 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 . . ? N1 C1 H1B 109.0 . . ? C2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? N2 C2 C3 122.4(4) . . ? N2 C2 C1 115.7(4) . . ? C3 C2 C1 121.9(4) . . ? C2 C3 C4 118.4(5) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 119.7(5) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 116.2(5) . . ? C6 C5 H5 121.9 . . ? C4 C5 H5 121.9 . . ? N2 C6 C5 126.1(5) . . ? N2 C6 Cl1 115.9(4) . . ? C5 C6 Cl1 118.0(4) . . ? N1 C7 C8 111.3(3) . . ? N1 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? N1 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? N3 C8 C9 122.6(4) . . ? N3 C8 C7 115.0(3) . . ? C9 C8 C7 122.2(4) . . ? C10 C9 C8 119.3(5) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 119.6(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 117.6(4) . . ? C10 C11 H11 121.2 . . ? C12 C11 H11 121.2 . . ? N3 C12 C11 123.7(5) . . ? N3 C12 Cl2 116.8(3) . . ? C11 C12 Cl2 119.5(4) . . ? N1 C13 C14 111.1(3) . . ? N1 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? N1 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? N4 C14 C15 122.6(4) . . ? N4 C14 C13 114.7(3) . . ? C15 C14 C13 122.5(4) . . ? C14 C15 C16 117.8(4) . . ? C14 C15 H15 121.1 . . ? C16 C15 H15 121.1 . . ? C17 C16 C15 119.2(4) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 118.4(4) . . ? C16 C17 H17 120.8 . . ? C18 C17 H17 120.8 . . ? N4 C18 C17 124.4(4) . . ? N4 C18 Cl3 116.6(3) . . ? C17 C18 Cl3 119.0(3) . . ? C7 N1 C13 109.9(3) . . ? C7 N1 C1 111.6(3) . . ? C13 N1 C1 113.3(3) . . ? C7 N1 Fe1 107.0(2) . . ? C13 N1 Fe1 106.1(2) . . ? C1 N1 Fe1 108.5(2) . . ? C6 N2 C2 117.2(4) . . ? C12 N3 C8 117.2(4) . . ? C12 N3 Fe1 130.0(3) . . ? C8 N3 Fe1 112.7(3) . . ? C18 N4 C14 117.4(4) . . ? C18 N4 Fe1 130.0(3) . . ? C14 N4 Fe1 112.2(3) . . ? N1 Fe1 N4 77.68(12) . . ? N1 Fe1 N3 76.97(12) . . ? N4 Fe1 N3 154.25(13) . . ? N1 Fe1 Cl4 111.83(9) . . ? N4 Fe1 Cl4 96.97(9) . . ? N3 Fe1 Cl4 96.56(9) . . ? N1 Fe1 Cl5 107.39(9) . . ? N4 Fe1 Cl5 91.05(9) . . ? N3 Fe1 Cl5 92.20(9) . . ? Cl4 Fe1 Cl5 140.78(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -81.6(4) . . . . ? N1 C1 C2 C3 96.8(5) . . . . ? N2 C2 C3 C4 1.9(7) . . . . ? C1 C2 C3 C4 -176.4(4) . . . . ? C2 C3 C4 C5 -0.9(7) . . . . ? C3 C4 C5 C6 0.3(7) . . . . ? C4 C5 C6 N2 -0.7(8) . . . . ? C4 C5 C6 Cl1 179.2(4) . . . . ? N1 C7 C8 N3 -38.5(5) . . . . ? N1 C7 C8 C9 146.8(4) . . . . ? N3 C8 C9 C10 -2.9(6) . . . . ? C7 C8 C9 C10 171.4(4) . . . . ? C8 C9 C10 C11 2.7(6) . . . . ? C9 C10 C11 C12 -1.7(6) . . . . ? C10 C11 C12 N3 0.8(6) . . . . ? C10 C11 C12 Cl2 -177.1(3) . . . . ? N1 C13 C14 N4 42.5(5) . . . . ? N1 C13 C14 C15 -143.4(4) . . . . ? N4 C14 C15 C16 3.6(6) . . . . ? C13 C14 C15 C16 -170.1(4) . . . . ? C14 C15 C16 C17 -0.9(6) . . . . ? C15 C16 C17 C18 -1.5(6) . . . . ? C16 C17 C18 N4 1.6(6) . . . . ? C16 C17 C18 Cl3 -178.1(3) . . . . ? C8 C7 N1 C13 159.9(3) . . . . ? C8 C7 N1 C1 -73.4(4) . . . . ? C8 C7 N1 Fe1 45.2(4) . . . . ? C14 C13 N1 C7 -161.5(3) . . . . ? C14 C13 N1 C1 72.9(4) . . . . ? C14 C13 N1 Fe1 -46.1(4) . . . . ? C2 C1 N1 C7 -66.7(4) . . . . ? C2 C1 N1 C13 58.1(4) . . . . ? C2 C1 N1 Fe1 175.6(3) . . . . ? C5 C6 N2 C2 1.7(7) . . . . ? Cl1 C6 N2 C2 -178.2(3) . . . . ? C3 C2 N2 C6 -2.3(6) . . . . ? C1 C2 N2 C6 176.1(4) . . . . ? C11 C12 N3 C8 -1.0(6) . . . . ? Cl2 C12 N3 C8 177.0(3) . . . . ? C11 C12 N3 Fe1 174.3(3) . . . . ? Cl2 C12 N3 Fe1 -7.6(5) . . . . ? C9 C8 N3 C12 2.0(6) . . . . ? C7 C8 N3 C12 -172.6(3) . . . . ? C9 C8 N3 Fe1 -174.1(3) . . . . ? C7 C8 N3 Fe1 11.2(4) . . . . ? C17 C18 N4 C14 1.0(6) . . . . ? Cl3 C18 N4 C14 -179.4(3) . . . . ? C17 C18 N4 Fe1 -171.7(3) . . . . ? Cl3 C18 N4 Fe1 7.9(5) . . . . ? C15 C14 N4 C18 -3.6(6) . . . . ? C13 C14 N4 C18 170.6(4) . . . . ? C15 C14 N4 Fe1 170.4(3) . . . . ? C13 C14 N4 Fe1 -15.5(4) . . . . ? C7 N1 Fe1 N4 145.9(2) . . . . ? C13 N1 Fe1 N4 28.6(2) . . . . ? C1 N1 Fe1 N4 -93.5(2) . . . . ? C7 N1 Fe1 N3 -29.5(2) . . . . ? C13 N1 Fe1 N3 -146.8(3) . . . . ? C1 N1 Fe1 N3 91.1(2) . . . . ? C7 N1 Fe1 Cl4 -121.4(2) . . . . ? C13 N1 Fe1 Cl4 121.2(2) . . . . ? C1 N1 Fe1 Cl4 -0.8(3) . . . . ? C7 N1 Fe1 Cl5 58.7(2) . . . . ? C13 N1 Fe1 Cl5 -58.6(3) . . . . ? C1 N1 Fe1 Cl5 179.3(2) . . . . ? C18 N4 Fe1 N1 165.1(4) . . . . ? C14 N4 Fe1 N1 -7.9(3) . . . . ? C18 N4 Fe1 N3 175.4(3) . . . . ? C14 N4 Fe1 N3 2.4(4) . . . . ? C18 N4 Fe1 Cl4 54.2(4) . . . . ? C14 N4 Fe1 Cl4 -118.8(3) . . . . ? C18 N4 Fe1 Cl5 -87.3(3) . . . . ? C14 N4 Fe1 Cl5 99.7(3) . . . . ? C12 N3 Fe1 N1 -164.9(4) . . . . ? C8 N3 Fe1 N1 10.7(3) . . . . ? C12 N3 Fe1 N4 -175.2(3) . . . . ? C8 N3 Fe1 N4 0.3(5) . . . . ? C12 N3 Fe1 Cl4 -53.9(4) . . . . ? C8 N3 Fe1 Cl4 121.6(3) . . . . ? C12 N3 Fe1 Cl5 87.8(3) . . . . ? C8 N3 Fe1 Cl5 -96.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.284 _refine_diff_density_min -0.811 _refine_diff_density_rms 0.132 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.032 0.000 0.000 286 141 ' ' _platon_squeeze_details ; The residual electron density was assigned to two molecules of the nitromethane solvent [141/2 = 70.5 e per asymetric unit; two molecules of CH3NO2 would give 64e]. ;