# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Palaniandavar, Mallayan' _publ_contact_author_name 'Palaniandavar, Mallayan' _publ_contact_author_email palanim51@yahoo.com _publ_section_title ; Novel Square Pyramidal Iron(III) Complexes of Linear Tetradentate Bis(phenolate) Ligands as Structural and Reactive Models for Intradiol-cleaving 3,4-PCD Enzymes: Quinone Formation Vs Intradiol Cleavage ; # Attachment '- 3.cif.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 770712' #TrackingRef '- 3.cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H29 Cl Fe N2 O2' _chemical_formula_weight 456.78 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 ORTHORHOMBIC _symmetry_space_group_name_H-M Cmc21 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 20.257(2) _cell_length_b 15.3291(17) _cell_length_c 7.3121(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2270.5(4) _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 'WINE red' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.802 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8370 _exptl_absorpt_correction_T_max 0.9534 _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 6558 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.24 _reflns_number_total 2487 _reflns_number_gt 2256 _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 'w=1/[\s^2^(Fo^2^)+(0.1019P)^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 0.17(4) _refine_ls_number_reflns 2487 _refine_ls_number_parameters 138 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1350 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.143 _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 0.0000 0.27115(4) 0.36764(11) 0.0308(2) Uani 1 d S . . Cl1 Cl 0.0000 0.40096(11) 0.5104(3) 0.0537(5) Uani 1 d S . . O1 O 0.06920(16) 0.2063(2) 0.4631(5) 0.0462(8) Uani 1 d . . . C6 C 0.1630(2) 0.2327(3) 0.2754(7) 0.0442(11) Uani 1 d . . . N1 N 0.06417(16) 0.2989(2) 0.1316(5) 0.0361(8) Uani 1 d . . . C2 C 0.1575(2) 0.1056(3) 0.4724(6) 0.0423(10) Uani 1 d . . . C1 C 0.12990(18) 0.1820(3) 0.4040(6) 0.0375(10) Uani 1 d . . . C8 C 0.0624(3) 0.2277(3) -0.0021(9) 0.0509(13) Uani 1 d . . . H8A H 0.0702 0.1730 0.0612 0.061 Uiso 1 calc R . . H8B H 0.0981 0.2359 -0.0889 0.061 Uiso 1 calc R . . C5 C 0.2244(2) 0.2042(4) 0.2124(7) 0.0483(11) Uani 1 d . . . H5 H 0.2467 0.2367 0.1244 0.058 Uiso 1 calc R . . C3 C 0.2185(2) 0.0805(3) 0.4065(7) 0.0498(13) Uani 1 d . . . H3 H 0.2372 0.0292 0.4507 0.060 Uiso 1 calc R . . C7 C 0.1326(2) 0.3141(3) 0.2037(7) 0.0437(10) Uani 1 d . . . H7A H 0.1601 0.3373 0.1065 0.052 Uiso 1 calc R . . H7B H 0.1309 0.3572 0.3008 0.052 Uiso 1 calc R . . C4 C 0.2529(2) 0.1279(4) 0.2789(7) 0.0487(12) Uani 1 d . . . C10 C 0.0382(2) 0.3818(3) 0.0543(7) 0.0457(11) Uani 1 d . . . H10A H 0.0542 0.3889 -0.0698 0.055 Uiso 1 calc R . . H10B H 0.0542 0.4305 0.1264 0.055 Uiso 1 calc R . . C12 C 0.3197(2) 0.0979(4) 0.2023(9) 0.0635(15) Uani 1 d . . . H12A H 0.3381 0.0540 0.2809 0.095 Uiso 1 calc R . . H12B H 0.3493 0.1467 0.1961 0.095 Uiso 1 calc R . . H12C H 0.3135 0.0741 0.0820 0.095 Uiso 1 calc R . . C11 C 0.1187(3) 0.0492(4) 0.6029(9) 0.0685(17) Uani 1 d . . . H11A H 0.1277 0.0669 0.7263 0.103 Uiso 1 calc R . . H11B H 0.1312 -0.0107 0.5871 0.103 Uiso 1 calc R . . H11C H 0.0724 0.0556 0.5783 0.103 Uiso 1 calc R . . C9 C 0.0000 0.2210(6) -0.1031(11) 0.066(2) Uani 1 d S . . H9 H 0.0000 0.2128 -0.2291 0.080 Uiso 1 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 0.0327(4) 0.0280(4) 0.0318(4) 0.0044(4) 0.000 0.000 Cl1 0.0687(11) 0.0369(8) 0.0553(10) -0.0090(7) 0.000 0.000 O1 0.0394(16) 0.0523(18) 0.047(2) 0.0177(16) 0.0031(14) 0.0172(14) C6 0.037(2) 0.057(3) 0.039(3) -0.002(2) -0.005(2) -0.0001(19) N1 0.0352(17) 0.0392(18) 0.0338(19) 0.0067(15) -0.0039(14) -0.0041(14) C2 0.045(2) 0.047(3) 0.035(3) -0.0005(19) -0.0073(18) 0.012(2) C1 0.0352(18) 0.043(2) 0.035(3) -0.0010(18) 0.0034(16) 0.0038(16) C8 0.044(2) 0.050(3) 0.058(4) -0.004(2) 0.007(2) 0.007(2) C5 0.035(2) 0.069(3) 0.041(3) -0.001(2) -0.002(2) 0.000(2) C3 0.049(2) 0.052(2) 0.049(4) -0.006(2) -0.019(2) 0.017(2) C7 0.034(2) 0.049(3) 0.048(3) 0.012(2) 0.0013(18) -0.0044(18) C4 0.033(2) 0.064(3) 0.050(3) -0.018(3) -0.008(2) 0.007(2) C10 0.040(2) 0.046(2) 0.051(3) 0.019(2) 0.0101(19) -0.0022(19) C12 0.041(3) 0.096(4) 0.054(3) -0.025(3) -0.006(2) 0.016(3) C11 0.077(4) 0.069(4) 0.059(4) 0.028(3) 0.007(3) 0.021(3) C9 0.064(4) 0.108(7) 0.028(5) -0.011(4) 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 O1 1.855(3) 4 ? Fe1 O1 1.855(3) . ? Fe1 N1 2.202(4) 4 ? Fe1 N1 2.202(4) . ? Fe1 Cl1 2.2470(18) . ? O1 C1 1.355(5) . ? C6 C1 1.393(7) . ? C6 C5 1.397(7) . ? C6 C7 1.486(7) . ? N1 C8 1.466(7) . ? N1 C10 1.487(6) . ? N1 C7 1.502(5) . ? C2 C3 1.380(7) . ? C2 C1 1.391(6) . ? C2 C11 1.509(8) . ? C8 C9 1.468(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C5 C4 1.392(8) . ? C5 H5 0.9300 . ? C3 C4 1.372(8) . ? C3 H3 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C4 C12 1.535(7) . ? C10 C10 1.549(8) 4 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C9 C8 1.468(7) 4 ? C9 H9 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 O1 Fe1 O1 98.2(2) 4 . ? O1 Fe1 N1 87.26(14) 4 4 ? O1 Fe1 N1 147.62(16) . 4 ? O1 Fe1 N1 147.62(16) 4 . ? O1 Fe1 N1 87.26(14) . . ? N1 Fe1 N1 72.36(18) 4 . ? O1 Fe1 Cl1 107.45(12) 4 . ? O1 Fe1 Cl1 107.45(12) . . ? N1 Fe1 Cl1 101.13(11) 4 . ? N1 Fe1 Cl1 101.13(11) . . ? C1 O1 Fe1 135.5(3) . . ? C1 C6 C5 118.4(4) . . ? C1 C6 C7 120.5(4) . . ? C5 C6 C7 121.0(5) . . ? C8 N1 C10 112.0(4) . . ? C8 N1 C7 111.9(4) . . ? C10 N1 C7 109.1(3) . . ? C8 N1 Fe1 111.4(3) . . ? C10 N1 Fe1 104.7(3) . . ? C7 N1 Fe1 107.4(3) . . ? C3 C2 C1 118.0(4) . . ? C3 C2 C11 121.9(4) . . ? C1 C2 C11 119.9(4) . . ? O1 C1 C2 118.8(4) . . ? O1 C1 C6 119.9(4) . . ? C2 C1 C6 121.3(4) . . ? N1 C8 C9 114.1(5) . . ? N1 C8 H8A 108.7 . . ? C9 C8 H8A 108.7 . . ? N1 C8 H8B 108.7 . . ? C9 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C4 C5 C6 121.2(5) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C4 C3 C2 123.0(4) . . ? C4 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? C6 C7 N1 112.1(4) . . ? C6 C7 H7A 109.2 . . ? N1 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? N1 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C3 C4 C5 118.1(4) . . ? C3 C4 C12 122.5(5) . . ? C5 C4 C12 119.3(5) . . ? N1 C10 C10 110.7(2) . 4 ? N1 C10 H10A 109.5 . . ? C10 C10 H10A 109.5 4 . ? N1 C10 H10B 109.5 . . ? C10 C10 H10B 109.5 4 . ? H10A C10 H10B 108.1 . . ? C4 C12 H12A 109.5 . . ? C4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C2 C11 H11A 109.5 . . ? C2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C9 C8 118.9(7) . 4 ? C8 C9 H9 120.5 . . ? C8 C9 H9 120.5 4 . ? _diffrn_measured_fraction_theta_max 0.480 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.480 _refine_diff_density_max 0.674 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.168