Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 ---------- X-Sun-Content-Length: 30708 X-Sun-Charset: iso-8859-1 X-Sun-Content-Lines: 881 data_B100913N _journal_coden_Cambridge 186 _audit_creation_method 'SHELXL97 and manual editing' # 1. SUBMISSION DETAILS _publ_contact_author_name 'Ademir Neves' _publ_contact_author_address ; Depto. Qu\'imica - UFSC 88040 - 900 Florian\'opolis, SC Brazil ; _publ_contact_author_email ademir@qmc.ufsc.br _publ_contact_author_fax '55(48)3316888' _publ_contact_author_phone '55(48)3316826' _publ_contact_letter ; Please consider this CIF file as supplementary material of the crystallographic study included in the paper above identified. ; _publ_requested_coeditor_name ? _publ_requested_journal ; Journal of the Chemical Society - Dalton Transactions ; _publ_requested_category ? # 3. TITLE AND AUTHOR LIST _publ_section_title ; A new Fe+++(m-OCH3)(m-OAc)Fe+++ complex containing phenolate and imidazole ligands as a structural model for the oxidized form of purple acid phosphatases ; loop_ _publ_author_name _publ_author_address 'Scarpellini, Marciela' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; 'Neves, Ademir' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; 'Bortoluzzi, Adailton J.' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; 'Vencato, Ivo' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; 'Drago, Valderes' ; Depto. F\'isica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; 'Ortiz, Wilson A.' ; Grupo de Supercondutividade e Magnetismo - Universidade Federal de São Carlos 13565-900 - São Carlos - SP Brazil ; 'Zucco, C\'esar' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; data_C28H37ClFe2N6O10 _database_code_CSD 157480 _chemical_name_systematic ; Di-\m-methoxo-\m-acetate-bis[(2-hydroxybenzyl)(2-(imidazol-2-yl)ethyl) amine]diiron(III) perchlorate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H37 Cl Fe2 N6 O10' _chemical_formula_weight 764.79 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 I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 12.540(2) _cell_length_b 12.624(2) _cell_length_c 41.336(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.69(3) _cell_angle_gamma 90.00 _cell_volume 6543.2(19) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.81 _cell_measurement_theta_max 15.28 _exptl_crystal_description prismatic _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3168 _exptl_absorpt_coefficient_mu 1.033 _exptl_absorpt_correction_type psi-scans _exptl_absorpt_correction_T_min 0.91565 _exptl_absorpt_correction_T_max 0.97881 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '120 min' _diffrn_standards_decay_% 1.3 _diffrn_reflns_number 6464 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0922 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -49 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6044 _reflns_number_gt 3205 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0786P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5751 _refine_ls_number_parameters 452 _refine_ls_number_restraints 102 _refine_ls_R_factor_all 0.1386 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1392 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.940 _refine_ls_shift/su_max 0.004 _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 Fe2 Fe 0.01175(5) 0.33420(5) 0.088378(15) 0.02890(19) Uani 1 d . . . Fe1 Fe 0.06183(5) 0.33281(5) 0.162118(15) 0.02716(19) Uani 1 d . . . O10 O -0.0211(3) 0.3683(2) 0.19937(7) 0.0336(8) Uani 1 d . . . O30 O 0.0941(3) 0.3647(2) 0.05051(7) 0.0368(8) Uani 1 d . . . O41 O 0.0609(2) 0.4925(2) 0.15170(7) 0.0348(8) Uani 1 d . . . O42 O 0.0138(3) 0.4931(2) 0.09941(7) 0.0360(8) Uani 1 d . . . O51 O -0.0589(2) 0.3037(2) 0.13151(7) 0.0277(7) Uani 1 d . . . O61 O 0.1307(2) 0.3016(2) 0.11897(7) 0.0300(7) Uani 1 d . . . N1 N 0.0677(3) 0.1717(3) 0.17927(9) 0.0332(9) Uani 1 d . . . H1 H 0.0786 0.1314 0.1614 0.040 Uiso 1 calc R . . N5 N 0.2134(3) 0.3554(3) 0.18340(9) 0.0336(10) Uani 1 d . . . N7 N 0.3624(4) 0.4350(4) 0.19678(10) 0.0472(12) Uani 1 d . . . H7 H 0.3991 0.4824 0.2002 0.056(19) Uiso 1 d R . . N21 N 0.0014(3) 0.1691(3) 0.07584(9) 0.0366(10) Uani 1 d . . . H21 H 0.0223 0.1359 0.0944 0.044 Uiso 1 calc R . . N25 N -0.1374(3) 0.3576(3) 0.06498(9) 0.0321(9) Uani 1 d . . . N27 N -0.2864(4) 0.4376(4) 0.05195(10) 0.0506(12) Uani 1 d . . . H27 H -0.3337 0.4865 0.0497 0.061 Uiso 1 calc R . . C2 C 0.1515(4) 0.1381(4) 0.20301(13) 0.0435(13) Uani 1 d . . . H2A H 0.1457 0.0624 0.2066 0.052 Uiso 1 calc R . . H2B H 0.1394 0.1734 0.2235 0.052 Uiso 1 calc R . . C3 C 0.2626(4) 0.1635(4) 0.19166(14) 0.0473(14) Uani 1 d . . . H3A H 0.3139 0.1263 0.2053 0.057 Uiso 1 calc R . . H3B H 0.2705 0.1377 0.1697 0.057 Uiso 1 calc R . . C4 C 0.2875(4) 0.2795(4) 0.19243(12) 0.0379(12) Uani 1 d . . . C6 C 0.2632(4) 0.4478(4) 0.18622(12) 0.0417(13) Uani 1 d . . . H6 H 0.2323 0.5130 0.1814 0.050 Uiso 1 calc R . . C8 C 0.3786(4) 0.3293(5) 0.20080(13) 0.0506(14) Uani 1 d . . . H8 H 0.4413 0.2972 0.2080 0.061 Uiso 1 calc R . . C10 C -0.0393(4) 0.1402(4) 0.19125(12) 0.0392(13) Uani 1 d . . . H10A H -0.0394 0.0648 0.1957 0.047 Uiso 1 calc R . . H10B H -0.0923 0.1538 0.1745 0.047 Uiso 1 calc R . . C11 C -0.0698(4) 0.1990(4) 0.22140(12) 0.0352(12) Uani 1 d . . . C12 C -0.0569(4) 0.3091(4) 0.22374(11) 0.0336(12) Uani 1 d . . . C13 C -0.0835(4) 0.3608(4) 0.25258(11) 0.0409(13) Uani 1 d . . . H13 H -0.0712 0.4331 0.2548 0.049 Uiso 1 calc R . . C14 C -0.1282(4) 0.3043(5) 0.27791(13) 0.0561(17) Uani 1 d . . . H14 H -0.1485 0.3397 0.2966 0.067 Uiso 1 calc R . . C15 C -0.1426(5) 0.1977(6) 0.27555(14) 0.0605(18) Uani 1 d . . . H15 H -0.1719 0.1602 0.2926 0.073 Uiso 1 calc R . . C16 C -0.1132(4) 0.1450(4) 0.24749(13) 0.0464(14) Uani 1 d . . . H16 H -0.1227 0.0721 0.2461 0.056 Uiso 1 calc R . . C22 C -0.1046(5) 0.1227(4) 0.06906(15) 0.0541(15) Uani 1 d . . . H22A H -0.1455 0.1246 0.0888 0.065 Uiso 1 calc R . . H22B H -0.0950 0.0488 0.0633 0.065 Uiso 1 calc R . . C23 C -0.1686(5) 0.1744(5) 0.04300(15) 0.0609(17) Uani 1 d . . . H23A H -0.1272 0.1742 0.0233 0.073 Uiso 1 calc R . . H23B H -0.2320 0.1322 0.0390 0.073 Uiso 1 calc R . . C24 C -0.2018(4) 0.2848(4) 0.04982(13) 0.0464(14) Uani 1 d . . . C26 C -0.1923(4) 0.4473(4) 0.06578(12) 0.0423(13) Uani 1 d . . . H26 H -0.1671 0.5098 0.0750 0.051 Uiso 1 calc R . . C28 C -0.2951(5) 0.3356(5) 0.04177(15) 0.0619(17) Uani 1 d . . . H28 H -0.3538 0.3057 0.0313 0.074 Uiso 1 calc R . . C30 C 0.0859(5) 0.1381(4) 0.05238(12) 0.0460(14) Uani 1 d . . . H30A H 0.0778 0.0635 0.0473 0.055 Uiso 1 calc R . . H30B H 0.1552 0.1475 0.0626 0.055 Uiso 1 calc R . . C31 C 0.0825(4) 0.2009(4) 0.02136(11) 0.0402(13) Uani 1 d . . . C32 C 0.0877(4) 0.3116(4) 0.02210(11) 0.0351(12) Uani 1 d . . . C33 C 0.0845(4) 0.3680(4) -0.00706(12) 0.0428(13) Uani 1 d . . . H33 H 0.0868 0.4416 -0.0069 0.051 Uiso 1 calc R . . C34 C 0.0779(5) 0.3140(5) -0.03629(13) 0.0567(16) Uani 1 d . . . H34 H 0.0755 0.3520 -0.0556 0.068 Uiso 1 calc R . . C35 C 0.0749(5) 0.2054(5) -0.03721(13) 0.0688(19) Uani 1 d . . . H35 H 0.0713 0.1698 -0.0569 0.083 Uiso 1 calc R . . C36 C 0.0771(5) 0.1499(5) -0.00849(13) 0.0573(16) Uani 1 d . . . H36 H 0.0750 0.0763 -0.0091 0.069 Uiso 1 calc R . . C43 C 0.0393(4) 0.5385(3) 0.12547(12) 0.0307(10) Uani 1 d . . . C44 C 0.0414(4) 0.6575(3) 0.12566(12) 0.0430(12) Uani 1 d . . . H44A H 0.0627 0.6822 0.1467 0.065 Uiso 1 calc R . . H44B H -0.0285 0.6841 0.1205 0.065 Uiso 1 calc R . . H44C H 0.0912 0.6823 0.1099 0.065 Uiso 1 calc R . . C52 C -0.1666(4) 0.3278(5) 0.13839(12) 0.0465(13) Uani 1 d . . . H52A H -0.2112 0.3069 0.1205 0.070 Uiso 1 calc R . . H52B H -0.1738 0.4026 0.1419 0.070 Uiso 1 calc R . . H52C H -0.1878 0.2902 0.1575 0.070 Uiso 1 calc R . . C62 C 0.2404(4) 0.3029(5) 0.11108(13) 0.0512(15) Uani 1 d . . . H62A H 0.2822 0.2844 0.1299 0.077 Uiso 1 calc R . . H62B H 0.2599 0.3724 0.1039 0.077 Uiso 1 calc R . . H62C H 0.2533 0.2526 0.0942 0.077 Uiso 1 calc R . . Cl Cl 0.12159(18) 0.94166(13) 0.12463(4) 0.0771(6) Uani 1 d D . . O1C O 0.1946(6) 0.8914(4) 0.14468(14) 0.153(3) Uani 1 d D . . O2C O 0.1344(10) 0.8965(10) 0.0934(2) 0.100(4) Uani 0.60 d PDU . . O2C' O 0.0947(15) 0.8851(18) 0.0974(3) 0.129(9) Uani 0.40 d PDU . . O3C O 0.1353(11) 1.0506(7) 0.1243(3) 0.092(4) Uani 0.60 d PDU . . O3C' O 0.1697(16) 1.0409(10) 0.1163(5) 0.125(9) Uani 0.40 d PDU . . O4C O 0.0213(8) 0.9210(11) 0.1374(4) 0.206(7) Uani 0.60 d PDU . . O4C' O 0.0304(11) 0.9635(16) 0.1426(5) 0.204(10) Uani 0.40 d PDU . . 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 Fe2 0.0327(4) 0.0261(4) 0.0279(4) -0.0002(3) 0.0006(3) -0.0005(3) Fe1 0.0295(4) 0.0239(4) 0.0282(4) 0.0025(3) 0.0013(3) -0.0010(3) O10 0.045(2) 0.0272(18) 0.0288(17) 0.0016(14) 0.0082(15) 0.0020(15) O30 0.045(2) 0.036(2) 0.0294(18) -0.0012(15) 0.0045(15) -0.0069(16) O41 0.043(2) 0.0255(17) 0.0358(19) 0.0036(15) -0.0037(15) -0.0004(16) O42 0.046(2) 0.0280(18) 0.0338(19) 0.0010(15) -0.0001(15) -0.0012(16) O51 0.0229(17) 0.0310(18) 0.0293(16) -0.0012(13) 0.0031(13) -0.0011(14) O61 0.0247(18) 0.0336(18) 0.0319(17) 0.0018(14) 0.0034(14) 0.0035(14) N1 0.040(2) 0.0182(19) 0.041(2) 0.0023(18) 0.0067(19) 0.0003(19) N5 0.035(2) 0.029(2) 0.037(2) 0.0010(17) -0.0035(19) -0.0001(19) N7 0.039(3) 0.046(3) 0.057(3) -0.007(2) -0.006(2) -0.016(2) N21 0.052(3) 0.024(2) 0.035(2) 0.0018(18) 0.0028(19) -0.001(2) N25 0.033(2) 0.032(2) 0.031(2) 0.0005(18) -0.0034(18) 0.0022(19) N27 0.039(3) 0.063(3) 0.050(3) 0.000(2) -0.007(2) 0.017(2) C2 0.049(3) 0.030(3) 0.051(3) 0.012(2) -0.001(3) 0.002(2) C3 0.043(3) 0.037(3) 0.062(4) 0.012(3) 0.006(3) 0.011(3) C4 0.034(3) 0.038(3) 0.042(3) 0.004(2) -0.002(2) 0.003(2) C6 0.045(4) 0.033(3) 0.047(3) -0.005(2) -0.003(3) -0.009(3) C8 0.035(3) 0.056(4) 0.061(4) 0.014(3) -0.007(3) 0.002(3) C10 0.042(3) 0.026(3) 0.050(3) 0.006(2) -0.002(2) -0.008(2) C11 0.029(3) 0.035(3) 0.042(3) 0.005(2) -0.002(2) -0.002(2) C12 0.025(3) 0.045(3) 0.031(3) 0.003(2) -0.002(2) 0.005(2) C13 0.042(3) 0.047(3) 0.034(3) -0.004(2) 0.003(2) 0.009(3) C14 0.046(4) 0.087(5) 0.036(3) 0.008(3) 0.008(3) 0.019(3) C15 0.048(4) 0.083(5) 0.051(4) 0.028(3) 0.015(3) 0.005(3) C16 0.035(3) 0.053(4) 0.051(3) 0.018(3) 0.001(3) -0.010(3) C22 0.060(4) 0.028(3) 0.074(4) -0.008(3) 0.001(3) -0.008(3) C23 0.053(4) 0.056(4) 0.073(4) -0.014(3) -0.005(3) -0.006(3) C24 0.043(3) 0.046(3) 0.050(3) -0.011(3) -0.007(3) 0.002(3) C26 0.047(4) 0.034(3) 0.045(3) 0.003(2) -0.002(3) -0.001(3) C28 0.041(4) 0.071(4) 0.074(4) -0.016(4) -0.008(3) -0.005(4) C30 0.066(4) 0.032(3) 0.040(3) -0.002(2) 0.007(3) 0.008(3) C31 0.044(3) 0.042(3) 0.035(3) -0.002(2) 0.006(2) 0.004(3) C32 0.032(3) 0.039(3) 0.035(3) -0.002(2) 0.006(2) -0.002(2) C33 0.048(3) 0.045(3) 0.036(3) 0.008(2) 0.005(2) -0.003(3) C34 0.063(4) 0.072(5) 0.035(3) 0.005(3) 0.004(3) -0.012(3) C35 0.100(6) 0.078(5) 0.029(3) -0.010(3) 0.010(3) -0.023(4) C36 0.080(5) 0.046(4) 0.046(3) -0.017(3) 0.013(3) -0.010(3) C43 0.031(3) 0.024(2) 0.037(3) 0.002(2) 0.003(2) 0.004(2) C44 0.056(3) 0.020(2) 0.053(3) 0.002(2) -0.007(3) -0.003(3) C52 0.037(3) 0.063(4) 0.039(3) -0.004(3) 0.005(2) 0.002(3) C62 0.031(3) 0.079(4) 0.044(3) 0.005(3) 0.010(2) -0.001(3) Cl 0.1275(18) 0.0377(9) 0.0659(11) -0.0077(8) -0.0013(11) 0.0223(10) O1C 0.236(8) 0.104(5) 0.119(5) 0.053(4) -0.038(5) 0.060(5) O2C 0.148(9) 0.064(7) 0.089(8) -0.042(6) 0.045(6) -0.036(7) O2C' 0.24(2) 0.098(12) 0.055(9) -0.011(8) 0.009(11) -0.100(13) O3C 0.195(11) 0.035(5) 0.046(6) -0.008(4) -0.015(6) 0.039(6) O3C' 0.25(2) 0.042(10) 0.080(13) -0.013(8) -0.033(13) -0.035(12) O4C 0.156(12) 0.109(11) 0.357(17) -0.095(11) 0.153(12) -0.019(8) O4C' 0.118(14) 0.166(19) 0.33(2) -0.183(16) 0.049(15) -0.019(12) 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 Fe2 O30 1.925(3) . y Fe2 O61 1.986(3) . y Fe2 O51 2.037(3) . y Fe2 O42 2.058(3) . y Fe2 N25 2.115(4) . y Fe2 N21 2.151(4) . y Fe2 Fe1 3.1047(11) . y Fe1 O10 1.922(3) . y Fe1 O51 1.996(3) . y Fe1 O61 2.029(3) . y Fe1 O41 2.061(3) . y Fe1 N5 2.104(4) . y Fe1 N1 2.155(4) . y O10 C12 1.337(5) . ? O30 C32 1.354(5) . ? O41 C43 1.257(5) . ? O42 C43 1.258(5) . ? O51 C52 1.416(5) . ? O61 C62 1.418(5) . ? N1 C10 1.490(6) . ? N1 C2 1.491(6) . ? N5 C6 1.328(6) . ? N5 C4 1.383(6) . ? N7 C6 1.324(6) . ? N7 C8 1.360(7) . ? N21 C22 1.477(6) . ? N21 C30 1.496(6) . ? N25 C26 1.327(6) . ? N25 C24 1.370(6) . ? N27 C26 1.311(6) . ? N27 C28 1.358(7) . ? C2 C3 1.510(7) . ? C3 C4 1.497(7) . ? C4 C8 1.345(7) . ? C10 C11 1.504(7) . ? C11 C16 1.392(7) . ? C11 C12 1.402(7) . ? C12 C13 1.403(7) . ? C13 C14 1.390(7) . ? C14 C15 1.362(9) . ? C15 C16 1.390(8) . ? C22 C23 1.486(8) . ? C23 C24 1.483(8) . ? C24 C28 1.372(8) . ? C30 C31 1.508(7) . ? C31 C36 1.393(7) . ? C31 C32 1.399(7) . ? C32 C33 1.400(6) . ? C33 C34 1.389(7) . ? C34 C35 1.372(8) . ? C35 C36 1.379(8) . ? C43 C44 1.503(6) . ? Cl O2C 1.420(8) . ? Cl O4C 1.393(10) . ? Cl O1C 1.382(5) . ? Cl O3C 1.386(9) . ? Cl O3C' 1.434(12) . ? Cl O4C' 1.399(13) . ? Cl O2C' 1.372(12) . ? O2C O2C' 0.55(2) . ? O3C O3C' 0.56(2) . ? O4C O4C' 0.59(2) . ? 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 O10 Fe1 O51 97.89(13) . . y O10 Fe1 O61 171.74(13) . . y O51 Fe1 O61 74.61(12) . . y O10 Fe1 O41 86.42(13) . . y O51 Fe1 O41 92.61(12) . . y O61 Fe1 O41 90.42(12) . . y O10 Fe1 N5 97.37(14) . . y O51 Fe1 N5 164.72(13) . . y O61 Fe1 N5 90.12(14) . . y O41 Fe1 N5 87.57(13) . . y O10 Fe1 N1 88.46(14) . . y O51 Fe1 N1 93.29(13) . . y O61 Fe1 N1 95.34(13) . . y O41 Fe1 N1 172.67(13) . . y N5 Fe1 N1 87.88(15) . . y O30 Fe2 O61 98.80(13) . . y O30 Fe2 O51 173.18(13) . . y O61 Fe2 O51 74.63(11) . . y O30 Fe2 O42 88.83(13) . . y O61 Fe2 O42 93.07(12) . . y O51 Fe2 O42 89.70(12) . . y O30 Fe2 N25 94.61(14) . . y O61 Fe2 N25 166.53(14) . . y O51 Fe2 N25 92.01(13) . . y O42 Fe2 N25 88.49(14) . . y O30 Fe2 N21 91.68(14) . . y O61 Fe2 N21 89.74(14) . . y O51 Fe2 N21 90.13(13) . . y O42 Fe2 N21 177.03(14) . . y N25 Fe2 N21 88.55(15) . . y C12 O10 Fe1 131.6(3) . . ? C32 O30 Fe2 125.4(3) . . ? C43 O41 Fe1 129.2(3) . . ? C43 O42 Fe2 129.5(3) . . ? C52 O51 Fe1 123.4(3) . . ? C52 O51 Fe2 124.1(3) . . ? Fe1 O51 Fe2 100.68(13) . . y C62 O61 Fe2 125.1(3) . . ? C62 O61 Fe1 128.6(3) . . ? Fe2 O61 Fe1 101.27(13) . . y C10 N1 C2 109.6(4) . . ? C10 N1 Fe1 109.5(3) . . ? C2 N1 Fe1 120.4(3) . . ? C6 N5 C4 105.8(4) . . ? C6 N5 Fe1 125.2(3) . . ? C4 N5 Fe1 128.3(3) . . ? C6 N7 C8 107.3(5) . . ? C22 N21 C30 114.6(4) . . ? C22 N21 Fe2 118.8(3) . . ? C30 N21 Fe2 111.6(3) . . ? C26 N25 C24 106.3(4) . . ? C26 N25 Fe2 124.4(3) . . ? C24 N25 Fe2 129.0(3) . . ? C26 N27 C28 107.1(5) . . ? N1 C2 C3 112.4(4) . . ? C4 C3 C2 113.2(4) . . ? C8 C4 N5 108.1(5) . . ? C8 C4 C3 129.7(5) . . ? N5 C4 C3 122.2(4) . . ? N7 C6 N5 111.2(5) . . ? C4 C8 N7 107.6(5) . . ? N1 C10 C11 112.5(4) . . ? C16 C11 C12 118.5(5) . . ? C16 C11 C10 120.4(4) . . ? C12 C11 C10 121.0(4) . . ? O10 C12 C11 122.8(4) . . ? O10 C12 C13 117.8(4) . . ? C11 C12 C13 119.4(5) . . ? C14 C13 C12 120.3(5) . . ? C15 C14 C13 120.4(5) . . ? C14 C15 C16 119.8(5) . . ? C15 C16 C11 121.5(5) . . ? N21 C22 C23 116.1(5) . . ? C24 C23 C22 115.2(5) . . ? N25 C24 C28 107.1(5) . . ? N25 C24 C23 123.5(5) . . ? C28 C24 C23 129.4(5) . . ? N27 C26 N25 112.0(5) . . ? N27 C28 C24 107.6(5) . . ? N21 C30 C31 113.6(4) . . ? C36 C31 C32 118.9(5) . . ? C36 C31 C30 120.7(5) . . ? C32 C31 C30 120.4(4) . . ? O30 C32 C31 121.1(4) . . ? O30 C32 C33 119.7(4) . . ? C31 C32 C33 119.2(5) . . ? C34 C33 C32 120.0(5) . . ? C35 C34 C33 121.1(5) . . ? C34 C35 C36 118.9(5) . . ? C35 C36 C31 121.9(5) . . ? O41 C43 O42 125.4(4) . . ? O41 C43 C44 117.0(4) . . ? O42 C43 C44 117.6(4) . . ? O2C Cl O4C 112.3(7) . . ? O2C Cl O1C 106.2(6) . . ? O4C Cl O1C 106.4(8) . . ? O2C Cl O3C 112.0(6) . . ? O4C Cl O3C 107.6(6) . . ? O1C Cl O3C 112.3(7) . . ? O2C Cl O3C' 94.5(11) . . ? O4C Cl O3C' 129.7(10) . . ? O1C Cl O3C' 105.6(8) . . ? O3C Cl O3C' 22.9(10) . . ? O2C Cl O4C' 131.6(10) . . ? O4C Cl O4C' 24.4(9) . . ? O1C Cl O4C' 108.2(10) . . ? O3C Cl O4C' 84.9(11) . . ? O3C' Cl O4C' 107.7(8) . . ? O2C Cl O2C' 22.4(10) . . ? O4C Cl O2C' 89.9(11) . . ? O1C Cl O2C' 114.1(10) . . ? O3C Cl O2C' 122.6(12) . . ? O3C' Cl O2C' 110.9(9) . . ? O4C' Cl O2C' 110.1(8) . . ? O2C' O2C Cl 73.8(18) . . ? O2C O2C' Cl 83.7(19) . . ? O3C' O3C Cl 83.4(18) . . ? O3C O3C' Cl 73.7(18) . . ? O4C' O4C Cl 78.3(17) . . ? O4C O4C' Cl 77.3(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O3C 0.91 1.98 2.874(13) 167.5 1_545 N1 H1 O3C' 0.91 2.48 3.35(2) 160.9 1_545 N21 H21 O3C 0.91 2.16 2.999(12) 153.4 1_545 N21 H21 O3C' 0.91 2.37 3.127(19) 140.3 1_545 N27 H27 O30 0.86 2.09 2.911(6) 160.7 6_565 N7 H7 O10 0.77 2.13 2.882(6) 165.2 6_665 _diffrn_measured_fraction_theta_max 0.476 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.476 _refine_diff_density_max 0.922 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.093 data_HBHA _database_code_CSD 157481 _chemical_name_systematic ; [(2-hydroxybenzyl)(2-(imidazol-2-yl)ethyl)amine] ; _chemical_name_common HBHA _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 N3 O' _chemical_formula_weight 217.27 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.956(2) _cell_length_b 10.419(2) _cell_length_c 11.095(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1151.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.153 _cell_measurement_theta_max 22.181 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '120 min' _diffrn_standards_decay_% 1.7 _diffrn_reflns_number 1677 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 28.48 _reflns_number_total 1676 _reflns_number_gt 1118 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+0.0958P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.020(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 1676 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 O1 O 0.22047(19) 0.93804(17) 0.73400(19) 0.0672(6) Uani 1 d . . . N8 N 0.31176(19) 0.64613(17) 0.69053(17) 0.0431(5) Uani 1 d . . . C7 C 0.1691(2) 0.6833(2) 0.6803(2) 0.0510(6) Uani 1 d . . . H7A H 0.1154 0.6080 0.6625 0.061 Uiso 1 calc R . . H7B H 0.1584 0.7438 0.6145 0.061 Uiso 1 calc R . . N14 N 0.6750(2) 0.89116(17) 0.71602(19) 0.0478(5) Uani 1 d . . . C1 C 0.1211(2) 0.7431(2) 0.7950(2) 0.0446(6) Uani 1 d . . . C11 C 0.6025(2) 0.7077(2) 0.6476(2) 0.0445(6) Uani 1 d . . . C10 C 0.5267(3) 0.6005(2) 0.5888(2) 0.0532(7) Uani 1 d . . . H10A H 0.5371 0.5235 0.6369 0.064 Uiso 1 calc R . . H10B H 0.5657 0.5839 0.5102 0.064 Uiso 1 calc R . . N12 N 0.7208(2) 0.68540(17) 0.7058(2) 0.0545(6) Uani 1 d . . . C15 C 0.5728(2) 0.8350(2) 0.6543(2) 0.0476(6) Uani 1 d . . . H15 H 0.4974 0.8756 0.6229 0.057 Uiso 1 calc R . . C9 C 0.3778(3) 0.6281(2) 0.5733(2) 0.0539(6) Uani 1 d . . . H9A H 0.3665 0.7049 0.5249 0.065 Uiso 1 calc R . . H9B H 0.3357 0.5572 0.5310 0.065 Uiso 1 calc R . . C2 C 0.1505(2) 0.8722(2) 0.8194(2) 0.0477(6) Uani 1 d . . . C6 C 0.0490(3) 0.6747(2) 0.8800(3) 0.0629(7) Uani 1 d . . . H6 H 0.0280 0.5893 0.8648 0.075 Uiso 1 calc R . . C13 C 0.7612(3) 0.7989(2) 0.7459(3) 0.0568(7) Uani 1 d . . . H13 H 0.8398 0.8123 0.7894 0.068 Uiso 1 calc R . . C3 C 0.1095(3) 0.9273(2) 0.9268(3) 0.0634(7) Uani 1 d . . . H3 H 0.1300 1.0126 0.9433 0.076 Uiso 1 calc R . . C5 C 0.0077(3) 0.7296(3) 0.9864(3) 0.0795(10) Uani 1 d . . . H5 H -0.0406 0.6818 1.0423 0.095 Uiso 1 calc R . . C4 C 0.0385(4) 0.8553(3) 1.0090(3) 0.0798(10) Uani 1 d . . . H4 H 0.0110 0.8927 1.0810 0.096 Uiso 1 calc R . . H14N H 0.681(2) 0.974(2) 0.740(2) 0.053(7) Uiso 1 d . . . H8N H 0.355(2) 0.706(2) 0.726(2) 0.050(7) Uiso 1 d . . . H1O H 0.235(3) 1.025(3) 0.764(3) 0.099(11) Uiso 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 O1 0.0818(13) 0.0362(9) 0.0837(13) -0.0055(10) 0.0222(12) -0.0144(9) N8 0.0536(11) 0.0304(9) 0.0453(11) -0.0020(8) -0.0050(10) -0.0005(9) C7 0.0568(14) 0.0334(12) 0.0628(16) -0.0011(11) -0.0165(13) 0.0004(11) N14 0.0578(12) 0.0273(9) 0.0582(12) -0.0067(9) 0.0034(10) -0.0003(9) C1 0.0439(12) 0.0302(10) 0.0598(15) 0.0035(11) -0.0090(12) 0.0055(9) C11 0.0595(14) 0.0282(10) 0.0457(12) -0.0033(9) 0.0149(12) -0.0034(10) C10 0.0733(17) 0.0314(12) 0.0548(15) -0.0073(10) 0.0160(14) -0.0062(12) N12 0.0570(12) 0.0344(10) 0.0721(14) -0.0057(11) 0.0038(12) 0.0086(9) C15 0.0591(14) 0.0302(11) 0.0535(13) -0.0008(10) -0.0029(13) -0.0004(10) C9 0.0783(17) 0.0379(12) 0.0455(13) -0.0042(11) -0.0004(13) -0.0110(13) C2 0.0479(13) 0.0330(11) 0.0623(14) 0.0012(11) 0.0018(12) 0.0019(10) C6 0.0776(17) 0.0296(12) 0.0814(19) 0.0130(13) 0.0013(17) 0.0022(13) C13 0.0535(14) 0.0421(13) 0.0749(17) -0.0085(13) 0.0006(14) 0.0061(11) C3 0.0793(17) 0.0336(12) 0.0773(18) -0.0038(13) 0.0120(17) 0.0052(13) C5 0.116(3) 0.0412(15) 0.081(2) 0.0206(15) 0.029(2) 0.0056(16) C4 0.119(3) 0.0484(15) 0.0715(18) 0.0059(14) 0.027(2) 0.0163(18) 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 O1 C2 1.361(3) . ? N8 C9 1.470(3) . y N8 C7 1.476(3) . y C7 C1 1.495(3) . ? N14 C13 1.331(3) . y N14 C15 1.359(3) . y C1 C6 1.383(3) . ? C1 C2 1.403(3) . ? C11 C15 1.362(3) . ? C11 N12 1.363(3) . y C11 C10 1.497(3) . ? C10 C9 1.519(4) . ? N12 C13 1.326(3) . y C2 C3 1.384(4) . ? C6 C5 1.374(4) . ? C3 C4 1.377(4) . ? C5 C4 1.369(4) . ? 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 C9 N8 C7 113.34(19) . . y N8 C7 C1 110.60(19) . . ? C13 N14 C15 107.31(18) . . y C6 C1 C2 118.1(2) . . ? C6 C1 C7 122.1(2) . . ? C2 C1 C7 119.8(2) . . ? C15 C11 N12 109.1(2) . . ? C15 C11 C10 129.8(2) . . ? N12 C11 C10 121.0(2) . . ? C11 C10 C9 113.6(2) . . ? C13 N12 C11 105.61(19) . . y N14 C15 C11 106.5(2) . . ? N8 C9 C10 111.1(2) . . ? O1 C2 C3 122.8(2) . . ? O1 C2 C1 117.1(2) . . ? C3 C2 C1 120.1(2) . . ? C5 C6 C1 121.8(2) . . ? N12 C13 N14 111.4(2) . . ? C4 C3 C2 119.8(2) . . ? C4 C5 C6 119.3(3) . . ? C5 C4 C3 121.0(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N14 H14N N8 0.90(2) 1.96(2) 2.855(3) 173(3) 3_656 O1 H1O N12 0.98(3) 1.76(3) 2.726(3) 170(3) 3_656 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.124 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.032