# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Paul Chirik' 'Suzanne C. Bart' 'Marco W. Bouwkamp' 'Eric J. Hawrelak' 'Emil Lobkovsky' 'Ryan J. Trovitch' _publ_contact_author_name 'Prof Paul Chirik' _publ_contact_author_address ; Department of Chemistry and Chemical Biology Cornell University Baker Laboratory Ithaca Ithaca NY 14853-1301 UNITED STATES OF AMERICA ; _publ_contact_author_email PC92@CORNELL.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Square planar bis(imino)pyridine iron halide and alkyl complexes ; data_eh14 _database_code_depnum_ccdc_archive 'CCDC 267323' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H46 Fe N3' _chemical_formula_weight 552.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 16.0725(12) _cell_length_b 16.2819(11) _cell_length_c 17.0074(12) _cell_angle_alpha 86.074(2) _cell_angle_beta 64.426(2) _cell_angle_gamma 62.003(2) _cell_volume 3494.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.050 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 0.454 _exptl_absorpt_correction_type 'semiempirical by SADABS' _exptl_absorpt_correction_T_min 0.8392 _exptl_absorpt_correction_T_max 0.9560 _exptl_absorpt_process_details ? _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 'Bruker X8 APEX II diffractometer' _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 17737 _diffrn_reflns_av_R_equivalents 0.0689 _diffrn_reflns_av_sigmaI/netI 0.0994 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 20.82 _reflns_number_total 7309 _reflns_number_gt 4939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. Due to a completely disordered solvent area, the data were corrected by PLATON Squeeze routine. ; _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^)+(0.0966P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7309 _refine_ls_number_parameters 685 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1091 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.1816 _refine_ls_wR_factor_gt 0.1627 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.009 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 0.73230(7) 0.36733(6) 0.04819(5) 0.0286(3) Uani 1 1 d . . . N1 N 0.7925(4) 0.2788(3) -0.0591(3) 0.0272(13) Uani 1 1 d . . . N2 N 0.6663(4) 0.4490(3) -0.0164(3) 0.0222(12) Uani 1 1 d . . . N3 N 0.6484(4) 0.4860(3) 0.1306(3) 0.0274(13) Uani 1 1 d . . . C1 C 0.7993(5) 0.2620(5) -0.2065(4) 0.0461(19) Uani 1 1 d . . . H1A H 0.8482 0.1956 -0.2102 0.069 Uiso 1 1 calc R . . H1B H 0.8357 0.2877 -0.2549 0.069 Uiso 1 1 calc R . . H1C H 0.7385 0.2671 -0.2112 0.069 Uiso 1 1 calc R . . C2 C 0.7627(5) 0.3156(4) -0.1213(4) 0.0277(16) Uani 1 1 d . . . C3 C 0.6903(5) 0.4150(4) -0.0978(4) 0.0261(16) Uani 1 1 d . . . C4 C 0.6471(5) 0.4743(5) -0.1496(4) 0.0363(17) Uani 1 1 d . . . H4A H 0.6636 0.4506 -0.2069 0.044 Uiso 1 1 calc R . . C5 C 0.5780(5) 0.5709(5) -0.1124(4) 0.0395(18) Uani 1 1 d . . . H5A H 0.5470 0.6132 -0.1453 0.047 Uiso 1 1 calc R . . C6 C 0.5550(5) 0.6046(5) -0.0297(4) 0.0371(17) Uani 1 1 d . . . H6A H 0.5085 0.6698 -0.0058 0.045 Uiso 1 1 calc R . . C7 C 0.6001(5) 0.5427(5) 0.0193(4) 0.0285(16) Uani 1 1 d . . . C8 C 0.5907(4) 0.5620(4) 0.1051(4) 0.0271(16) Uani 1 1 d . . . C9 C 0.5204(5) 0.6587(5) 0.1590(4) 0.050(2) Uani 1 1 d . . . H9A H 0.5247 0.6575 0.2148 0.075 Uiso 1 1 calc R . . H9B H 0.4473 0.6797 0.1713 0.075 Uiso 1 1 calc R . . H9C H 0.5430 0.7023 0.1261 0.075 Uiso 1 1 calc R . . C10 C 0.8118(5) 0.2795(4) 0.1097(4) 0.0448(19) Uani 1 1 d . . . H10A H 0.7903 0.3137 0.1662 0.067 Uiso 1 1 calc R . . H10B H 0.8878 0.2545 0.0725 0.067 Uiso 1 1 calc R . . H10C H 0.7962 0.2272 0.1204 0.067 Uiso 1 1 calc R . . C11 C 0.8613(5) 0.1772(4) -0.0742(4) 0.0304(16) Uani 1 1 d . . . C12 C 0.9707(5) 0.1400(5) -0.1122(4) 0.0372(17) Uani 1 1 d . . . C13 C 1.0328(6) 0.0441(5) -0.1229(5) 0.050(2) Uani 1 1 d . . . H13A H 1.1075 0.0174 -0.1504 0.060 Uiso 1 1 calc R . . C14 C 0.9899(7) -0.0134(5) -0.0952(5) 0.054(2) Uani 1 1 d . . . H14A H 1.0342 -0.0795 -0.1029 0.065 Uiso 1 1 calc R . . C15 C 0.8818(7) 0.0243(5) -0.0559(5) 0.047(2) Uani 1 1 d . . . H15A H 0.8524 -0.0165 -0.0370 0.057 Uiso 1 1 calc R . . C16 C 0.8151(5) 0.1200(5) -0.0434(4) 0.0356(17) Uani 1 1 d . . . C17 C 1.0209(5) 0.2033(5) -0.1426(5) 0.053(2) Uani 1 1 d . . . H17A H 0.9628 0.2705 -0.1226 0.064 Uiso 1 1 calc R . . C18 C 1.0958(6) 0.1883(6) -0.1015(5) 0.074(3) Uani 1 1 d . . . H18A H 1.1265 0.2300 -0.1224 0.110 Uiso 1 1 calc R . . H18B H 1.1526 0.1225 -0.1193 0.110 Uiso 1 1 calc R . . H18C H 1.0556 0.2030 -0.0369 0.110 Uiso 1 1 calc R . . C19 C 1.0826(6) 0.1870(5) -0.2431(5) 0.069(2) Uani 1 1 d . . . H19A H 1.0360 0.1964 -0.2695 0.103 Uiso 1 1 calc R . . H19B H 1.1421 0.1225 -0.2640 0.103 Uiso 1 1 calc R . . H19C H 1.1094 0.2319 -0.2603 0.103 Uiso 1 1 calc R . . C20 C 0.6953(5) 0.1606(5) 0.0039(5) 0.056(2) Uani 1 1 d . . . H20A H 0.6619 0.2304 0.0055 0.067 Uiso 1 1 calc R . . C21 C 0.6592(7) 0.1431(7) 0.0981(6) 0.099(3) Uani 1 1 d . . . H21A H 0.6839 0.1687 0.1285 0.149 Uiso 1 1 calc R . . H21B H 0.6884 0.0750 0.0984 0.149 Uiso 1 1 calc R . . H21C H 0.5818 0.1741 0.1286 0.149 Uiso 1 1 calc R . . C22 C 0.6574(6) 0.1210(6) -0.0456(5) 0.069(2) Uani 1 1 d . . . H22A H 0.5804 0.1486 -0.0134 0.104 Uiso 1 1 calc R . . H22B H 0.6907 0.0523 -0.0497 0.104 Uiso 1 1 calc R . . H22C H 0.6772 0.1370 -0.1052 0.104 Uiso 1 1 calc R . . C23 C 0.6467(5) 0.4992(4) 0.2144(4) 0.0264(15) Uani 1 1 d . . . C24 C 0.7153(5) 0.5245(4) 0.2192(4) 0.0309(16) Uani 1 1 d . . . C25 C 0.7138(5) 0.5326(5) 0.3001(4) 0.0408(18) Uani 1 1 d . . . H25A H 0.7594 0.5515 0.3047 0.049 Uiso 1 1 calc R . . C26 C 0.6482(5) 0.5140(5) 0.3742(4) 0.048(2) Uani 1 1 d . . . H26A H 0.6492 0.5191 0.4291 0.057 Uiso 1 1 calc R . . C27 C 0.5816(6) 0.4881(5) 0.3677(4) 0.050(2) Uani 1 1 d . . . H27A H 0.5362 0.4751 0.4187 0.060 Uiso 1 1 calc R . . C28 C 0.5789(5) 0.4803(5) 0.2883(4) 0.0391(18) Uani 1 1 d . . . C30 C 0.7937(7) 0.6315(6) 0.1520(5) 0.076(3) Uani 1 1 d . . . H30A H 0.7219 0.6852 0.1738 0.114 Uiso 1 1 calc R . . H30B H 0.8404 0.6407 0.0961 0.114 Uiso 1 1 calc R . . H30C H 0.8196 0.6268 0.1957 0.114 Uiso 1 1 calc R . . C31 C 0.9029(6) 0.4552(6) 0.1030(6) 0.086(3) Uani 1 1 d . . . H31A H 0.8999 0.3980 0.0939 0.130 Uiso 1 1 calc R . . H31B H 0.9294 0.4493 0.1464 0.130 Uiso 1 1 calc R . . H31C H 0.9503 0.4633 0.0468 0.130 Uiso 1 1 calc R . . C32 C 0.5043(6) 0.4488(6) 0.2848(4) 0.057(2) Uani 1 1 d . . . H32A H 0.5062 0.4561 0.2252 0.069 Uiso 1 1 calc R . . C33 C 0.5432(6) 0.3439(6) 0.2920(6) 0.077(3) Uani 1 1 d . . . H33A H 0.4941 0.3257 0.2895 0.115 Uiso 1 1 calc R . . H33B H 0.5466 0.3332 0.3482 0.115 Uiso 1 1 calc R . . H33C H 0.6137 0.3058 0.2429 0.115 Uiso 1 1 calc R . . C34 C 0.3902(6) 0.5094(7) 0.3529(5) 0.075(3) Uani 1 1 d . . . H34A H 0.3674 0.5759 0.3469 0.113 Uiso 1 1 calc R . . H34B H 0.3842 0.5012 0.4124 0.113 Uiso 1 1 calc R . . H34C H 0.3452 0.4904 0.3435 0.113 Uiso 1 1 calc R . . C39 C 0.7923(5) 0.5405(5) 0.1370(4) 0.0443(19) Uani 1 1 d . . . H39A H 0.7689 0.5463 0.0902 0.053 Uiso 1 1 calc R . . Fe1' Fe 1.22389(7) 0.23592(6) 0.34492(5) 0.0291(3) Uani 1 1 d . . . N1' N 1.3021(4) 0.1387(3) 0.3963(3) 0.0322(13) Uani 1 1 d . . . N2' N 1.1179(4) 0.2117(3) 0.4257(3) 0.0296(13) Uani 1 1 d . . . N3' N 1.1076(4) 0.3231(3) 0.3201(3) 0.0264(13) Uani 1 1 d . . . C1' C 1.2960(6) 0.0311(5) 0.5086(5) 0.054(2) Uani 1 1 d . . . H1'A H 1.3711 0.0117 0.4854 0.081 Uiso 1 1 calc R . . H1'B H 1.2886 -0.0237 0.5006 0.081 Uiso 1 1 calc R . . H1'C H 1.2592 0.0571 0.5718 0.081 Uiso 1 1 calc R . . C2' C 1.2492(5) 0.1044(4) 0.4603(4) 0.0355(17) Uani 1 1 d . . . C3' C 1.1398(5) 0.1474(5) 0.4790(4) 0.0342(17) Uani 1 1 d . . . C4' C 1.0595(6) 0.1300(5) 0.5410(4) 0.047(2) Uani 1 1 d . . . H4'A H 1.0739 0.0844 0.5780 0.056 Uiso 1 1 calc R . . C5' C 0.9579(6) 0.1814(6) 0.5468(5) 0.058(2) Uani 1 1 d . . . H5'A H 0.9028 0.1707 0.5884 0.069 Uiso 1 1 calc R . . C6' C 0.9375(5) 0.2469(5) 0.4932(5) 0.048(2) Uani 1 1 d . . . H6'A H 0.8680 0.2823 0.4986 0.058 Uiso 1 1 calc R . . C7' C 1.0186(5) 0.2620(5) 0.4304(4) 0.0349(17) Uani 1 1 d . . . C8' C 1.0160(5) 0.3257(5) 0.3686(4) 0.0331(17) Uani 1 1 d . . . C9' C 0.9167(5) 0.3883(5) 0.3597(5) 0.051(2) Uani 1 1 d . . . H9'A H 0.9308 0.4267 0.3141 0.077 Uiso 1 1 calc R . . H9'B H 0.8610 0.4298 0.4163 0.077 Uiso 1 1 calc R . . H9'C H 0.8936 0.3493 0.3430 0.077 Uiso 1 1 calc R . . C10' C 1.3337(5) 0.2685(5) 0.2656(4) 0.048(2) Uani 1 1 d . . . H10D H 1.3991 0.2293 0.2708 0.073 Uiso 1 1 calc R . . H10E H 1.3090 0.3352 0.2826 0.073 Uiso 1 1 calc R . . H10F H 1.3473 0.2570 0.2044 0.073 Uiso 1 1 calc R . . C11' C 1.4122(5) 0.1043(4) 0.3727(4) 0.0335(17) Uani 1 1 d . . . C12' C 1.4879(6) 0.0367(5) 0.2972(5) 0.0438(19) Uani 1 1 d . . . C13' C 1.5941(6) 0.0099(5) 0.2694(5) 0.058(2) Uani 1 1 d . . . H13B H 1.6478 -0.0367 0.2184 0.070 Uiso 1 1 calc R . . C14' C 1.6216(6) 0.0520(6) 0.3169(6) 0.062(3) Uani 1 1 d . . . H14B H 1.6936 0.0349 0.2965 0.074 Uiso 1 1 calc R . . C15' C 1.5447(6) 0.1179(5) 0.3929(5) 0.047(2) Uani 1 1 d . . . H15B H 1.5647 0.1446 0.4250 0.056 Uiso 1 1 calc R . . C16' C 1.4387(5) 0.1455(5) 0.4229(4) 0.0392(18) Uani 1 1 d . . . C17' C 1.4614(6) -0.0079(5) 0.2448(5) 0.064(2) Uani 1 1 d . . . H17B H 1.3828 0.0200 0.2739 0.077 Uiso 1 1 calc R . . C18' C 1.4954(10) 0.0072(8) 0.1505(6) 0.125(4) Uani 1 1 d . . . H18D H 1.4660 0.0750 0.1487 0.187 Uiso 1 1 calc R . . H18E H 1.4697 -0.0196 0.1223 0.187 Uiso 1 1 calc R . . H18F H 1.5728 -0.0240 0.1189 0.187 Uiso 1 1 calc R . . C19' C 1.5087(13) -0.1127(8) 0.2435(9) 0.188(7) Uani 1 1 d . . . H19D H 1.4881 -0.1254 0.3043 0.282 Uiso 1 1 calc R . . H19E H 1.5859 -0.1427 0.2111 0.282 Uiso 1 1 calc R . . H19F H 1.4829 -0.1384 0.2144 0.282 Uiso 1 1 calc R . . C20' C 1.3543(5) 0.2170(5) 0.5062(4) 0.0421(18) Uani 1 1 d . . . H20B H 1.2854 0.2200 0.5212 0.050 Uiso 1 1 calc R . . C21' C 1.3431(6) 0.3151(5) 0.4905(5) 0.061(2) Uani 1 1 d . . . H21D H 1.3270 0.3324 0.4404 0.091 Uiso 1 1 calc R . . H21E H 1.4094 0.3138 0.4774 0.091 Uiso 1 1 calc R . . H21F H 1.2857 0.3618 0.5436 0.091 Uiso 1 1 calc R . . C22' C 1.3796(6) 0.1900(6) 0.5850(5) 0.070(2) Uani 1 1 d . . . H22D H 1.3867 0.1275 0.5951 0.105 Uiso 1 1 calc R . . H22E H 1.3222 0.2367 0.6381 0.105 Uiso 1 1 calc R . . H22F H 1.4459 0.1886 0.5719 0.105 Uiso 1 1 calc R . . C23' C 1.1150(4) 0.3826(5) 0.2536(4) 0.0269(16) Uani 1 1 d . . . C24' C 1.1598(5) 0.3427(5) 0.1660(4) 0.0339(17) Uani 1 1 d . . . C25' C 1.1671(5) 0.4023(6) 0.1036(4) 0.0438(19) Uani 1 1 d . . . H25B H 1.1976 0.3768 0.0431 0.053 Uiso 1 1 calc R . . C26' C 1.1323(5) 0.4950(6) 0.1255(5) 0.0441(19) Uani 1 1 d . . . H26B H 1.1365 0.5339 0.0812 0.053 Uiso 1 1 calc R . . C27' C 1.0910(5) 0.5321(5) 0.2123(5) 0.0381(18) Uani 1 1 d . . . H27B H 1.0682 0.5967 0.2276 0.046 Uiso 1 1 calc R . . C28' C 1.0817(4) 0.4765(5) 0.2785(4) 0.0300(17) Uani 1 1 d . . . C29' C 1.2011(6) 0.2396(5) 0.1379(4) 0.053(2) Uani 1 1 d . . . H29A H 1.2089 0.2065 0.1881 0.063 Uiso 1 1 calc R . . C30' C 1.1226(8) 0.2259(6) 0.1216(7) 0.100(3) Uani 1 1 d . . . H30D H 1.0535 0.2562 0.1738 0.150 Uiso 1 1 calc R . . H30E H 1.1472 0.1583 0.1100 0.150 Uiso 1 1 calc R . . H30F H 1.1162 0.2543 0.0704 0.150 Uiso 1 1 calc R . . C31' C 1.3093(7) 0.1927(6) 0.0570(5) 0.090(3) Uani 1 1 d . . . H31D H 1.3595 0.2020 0.0683 0.135 Uiso 1 1 calc R . . H31E H 1.3034 0.2211 0.0057 0.135 Uiso 1 1 calc R . . H31F H 1.3344 0.1250 0.0453 0.135 Uiso 1 1 calc R . . C32' C 1.0412(5) 0.5177(5) 0.3736(4) 0.0394(18) Uani 1 1 d . . . H32B H 1.0227 0.4738 0.4125 0.047 Uiso 1 1 calc R . . C33' C 1.1267(6) 0.5255(6) 0.3863(5) 0.071(3) Uani 1 1 d . . . H33D H 1.1907 0.4636 0.3665 0.107 Uiso 1 1 calc R . . H33E H 1.1006 0.5467 0.4490 0.107 Uiso 1 1 calc R . . H33F H 1.1432 0.5710 0.3515 0.107 Uiso 1 1 calc R . . C34' C 0.9422(6) 0.6148(5) 0.4049(5) 0.074(3) Uani 1 1 d . . . H34D H 0.8870 0.6109 0.3972 0.111 Uiso 1 1 calc R . . H34E H 0.9593 0.6601 0.3700 0.111 Uiso 1 1 calc R . . H34F H 0.9167 0.6357 0.4675 0.111 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 0.0338(6) 0.0281(6) 0.0216(5) 0.0065(4) -0.0130(5) -0.0133(5) N1 0.030(3) 0.024(3) 0.024(3) 0.000(3) -0.010(3) -0.012(3) N2 0.024(3) 0.028(4) 0.014(3) 0.005(3) -0.010(2) -0.012(3) N3 0.026(3) 0.035(3) 0.023(3) 0.008(3) -0.011(3) -0.016(3) C1 0.060(5) 0.040(5) 0.035(4) 0.004(4) -0.023(4) -0.020(4) C2 0.034(4) 0.031(5) 0.018(4) 0.003(3) -0.010(3) -0.017(4) C3 0.034(4) 0.036(5) 0.019(4) 0.012(3) -0.015(3) -0.023(4) C4 0.040(4) 0.043(5) 0.029(4) 0.013(4) -0.018(4) -0.021(4) C5 0.058(5) 0.049(6) 0.036(5) 0.020(4) -0.035(4) -0.033(4) C6 0.045(4) 0.035(4) 0.037(4) 0.014(4) -0.028(4) -0.016(4) C7 0.028(4) 0.031(5) 0.027(4) 0.006(4) -0.012(3) -0.015(4) C8 0.023(4) 0.029(4) 0.020(4) 0.002(3) -0.005(3) -0.011(3) C9 0.052(5) 0.045(5) 0.043(4) -0.003(4) -0.024(4) -0.013(4) C10 0.047(5) 0.036(4) 0.033(4) 0.002(3) -0.018(4) -0.006(4) C11 0.041(5) 0.024(4) 0.021(4) 0.002(3) -0.012(3) -0.013(4) C12 0.038(5) 0.038(5) 0.032(4) 0.003(4) -0.013(4) -0.018(4) C13 0.042(5) 0.033(5) 0.055(5) -0.002(4) -0.017(4) -0.007(4) C14 0.062(6) 0.027(5) 0.053(5) -0.001(4) -0.023(5) -0.009(5) C15 0.070(6) 0.039(5) 0.044(5) 0.012(4) -0.025(4) -0.036(5) C16 0.046(5) 0.016(4) 0.044(4) 0.007(3) -0.022(4) -0.014(4) C17 0.038(5) 0.042(5) 0.058(5) 0.002(4) -0.008(4) -0.014(4) C18 0.065(6) 0.088(7) 0.080(6) 0.004(5) -0.028(5) -0.050(5) C19 0.060(5) 0.060(6) 0.065(6) 0.023(5) -0.018(5) -0.024(4) C20 0.039(5) 0.036(5) 0.082(6) 0.016(4) -0.019(5) -0.020(4) C21 0.069(6) 0.141(9) 0.066(7) -0.020(6) 0.007(5) -0.063(7) C22 0.060(6) 0.083(7) 0.078(6) 0.027(5) -0.035(5) -0.043(5) C23 0.032(4) 0.034(4) 0.017(4) 0.003(3) -0.014(3) -0.016(3) C24 0.034(4) 0.038(4) 0.027(4) 0.012(3) -0.018(3) -0.019(3) C25 0.045(5) 0.060(5) 0.039(5) 0.010(4) -0.026(4) -0.035(4) C26 0.054(5) 0.078(6) 0.027(4) 0.014(4) -0.026(4) -0.037(5) C27 0.057(5) 0.088(6) 0.026(4) 0.021(4) -0.019(4) -0.051(5) C28 0.044(4) 0.067(5) 0.024(4) 0.013(4) -0.019(4) -0.037(4) C30 0.112(7) 0.075(7) 0.064(6) 0.029(5) -0.035(5) -0.069(6) C31 0.048(6) 0.088(7) 0.084(7) 0.016(6) 0.007(5) -0.038(5) C32 0.075(6) 0.104(7) 0.024(4) 0.014(4) -0.025(4) -0.064(5) C33 0.073(6) 0.090(7) 0.072(6) -0.002(5) -0.014(5) -0.058(6) C34 0.044(5) 0.149(9) 0.049(5) 0.040(6) -0.025(5) -0.058(6) C39 0.051(5) 0.064(6) 0.040(4) 0.017(4) -0.026(4) -0.040(4) Fe1' 0.0298(6) 0.0329(6) 0.0238(5) 0.0081(4) -0.0105(5) -0.0167(5) N1' 0.028(3) 0.033(3) 0.036(3) 0.008(3) -0.015(3) -0.015(3) N2' 0.036(4) 0.036(3) 0.021(3) 0.010(3) -0.013(3) -0.021(3) N3' 0.025(3) 0.032(3) 0.024(3) 0.004(3) -0.009(3) -0.017(3) C1' 0.064(5) 0.058(5) 0.045(5) 0.029(4) -0.025(4) -0.036(4) C2' 0.042(5) 0.038(4) 0.029(4) 0.015(4) -0.015(4) -0.023(4) C3' 0.049(5) 0.037(4) 0.024(4) 0.009(4) -0.017(4) -0.027(4) C4' 0.066(6) 0.065(5) 0.032(4) 0.022(4) -0.024(4) -0.049(5) C5' 0.058(6) 0.090(6) 0.050(5) 0.041(5) -0.027(4) -0.056(5) C6' 0.037(5) 0.064(5) 0.049(5) 0.011(4) -0.020(4) -0.028(4) C7' 0.035(4) 0.055(5) 0.030(4) 0.010(4) -0.019(4) -0.030(4) C8' 0.029(4) 0.050(5) 0.023(4) 0.004(4) -0.013(3) -0.021(4) C9' 0.041(5) 0.069(6) 0.052(5) 0.021(4) -0.025(4) -0.031(4) C10' 0.034(4) 0.053(5) 0.048(5) 0.025(4) -0.015(4) -0.019(4) C11' 0.032(4) 0.029(4) 0.028(4) 0.012(4) -0.013(4) -0.008(4) C12' 0.047(5) 0.029(5) 0.037(5) 0.005(4) -0.012(4) -0.011(4) C13' 0.046(6) 0.046(5) 0.047(5) 0.010(4) -0.012(5) -0.004(4) C14' 0.024(5) 0.064(6) 0.055(6) 0.029(5) -0.008(5) -0.002(4) C15' 0.034(5) 0.065(6) 0.048(5) 0.027(5) -0.027(4) -0.024(4) C16' 0.037(5) 0.044(5) 0.037(4) 0.023(4) -0.021(4) -0.018(4) C17' 0.061(6) 0.045(6) 0.049(5) -0.010(4) -0.001(4) -0.019(4) C18' 0.212(13) 0.146(11) 0.077(8) 0.037(7) -0.078(8) -0.124(10) C19' 0.37(2) 0.073(9) 0.206(15) 0.059(9) -0.201(16) -0.116(12) C20' 0.042(4) 0.052(5) 0.032(4) 0.008(4) -0.019(4) -0.021(4) C21' 0.063(5) 0.062(6) 0.054(5) 0.001(4) -0.019(4) -0.035(5) C22' 0.078(6) 0.088(7) 0.039(5) 0.007(5) -0.022(5) -0.040(5) C23' 0.027(4) 0.036(5) 0.020(4) 0.013(4) -0.015(3) -0.015(3) C24' 0.041(4) 0.041(5) 0.033(5) 0.019(4) -0.024(4) -0.025(4) C25' 0.046(5) 0.059(6) 0.025(4) 0.006(4) -0.014(4) -0.026(4) C26' 0.048(5) 0.062(6) 0.033(5) 0.020(4) -0.019(4) -0.034(4) C27' 0.033(4) 0.036(4) 0.047(5) 0.006(4) -0.017(4) -0.019(3) C28' 0.027(4) 0.038(5) 0.029(4) 0.015(4) -0.013(3) -0.020(3) C29' 0.079(6) 0.045(6) 0.033(4) 0.011(4) -0.029(4) -0.025(5) C30' 0.121(9) 0.068(7) 0.138(9) 0.002(6) -0.074(8) -0.051(6) C31' 0.086(7) 0.073(7) 0.057(6) -0.009(5) -0.011(6) -0.016(5) C32' 0.049(5) 0.039(5) 0.028(4) 0.006(3) -0.015(4) -0.021(4) C33' 0.061(5) 0.106(7) 0.050(5) -0.005(5) -0.026(5) -0.041(5) C34' 0.056(5) 0.073(6) 0.062(6) -0.002(5) -0.024(5) -0.009(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N2 1.893(4) . ? Fe1 N3 1.952(5) . ? Fe1 N1 1.968(5) . ? Fe1 C10 2.001(6) . ? N1 C2 1.337(7) . ? N1 C11 1.455(7) . ? N2 C3 1.349(7) . ? N2 C7 1.368(7) . ? N3 C8 1.332(7) . ? N3 C23 1.442(7) . ? C1 C2 1.471(8) . ? C2 C3 1.432(8) . ? C3 C4 1.403(8) . ? C4 C5 1.413(9) . ? C5 C6 1.372(9) . ? C6 C7 1.398(8) . ? C7 C8 1.442(8) . ? C8 C9 1.493(8) . ? C11 C16 1.393(8) . ? C11 C12 1.397(8) . ? C12 C13 1.373(9) . ? C12 C17 1.526(9) . ? C13 C14 1.357(10) . ? C14 C15 1.375(9) . ? C15 C16 1.378(9) . ? C16 C20 1.528(9) . ? C17 C19 1.525(10) . ? C17 C18 1.558(10) . ? C20 C21 1.508(11) . ? C20 C22 1.542(10) . ? C23 C24 1.379(8) . ? C23 C28 1.393(8) . ? C24 C25 1.380(9) . ? C24 C39 1.521(8) . ? C25 C26 1.376(8) . ? C26 C27 1.367(9) . ? C27 C28 1.386(9) . ? C28 C32 1.532(9) . ? C30 C39 1.532(9) . ? C31 C39 1.525(10) . ? C32 C34 1.517(10) . ? C32 C33 1.536(10) . ? Fe1' N2' 1.866(5) . ? Fe1' N1' 1.935(5) . ? Fe1' N3' 1.947(5) . ? Fe1' C10' 1.985(6) . ? N1' C2' 1.335(7) . ? N1' C11' 1.446(8) . ? N2' C3' 1.357(7) . ? N2' C7' 1.377(7) . ? N3' C8' 1.322(7) . ? N3' C23' 1.440(7) . ? C1' C2' 1.492(8) . ? C2' C3' 1.440(9) . ? C3' C4' 1.408(9) . ? C4' C5' 1.402(9) . ? C5' C6' 1.369(9) . ? C6' C7' 1.401(9) . ? C7' C8' 1.423(8) . ? C8' C9' 1.507(8) . ? C11' C12' 1.388(9) . ? C11' C16' 1.421(9) . ? C12' C13' 1.401(10) . ? C12' C17' 1.486(10) . ? C13' C14' 1.407(11) . ? C14' C15' 1.385(10) . ? C15' C16' 1.388(9) . ? C16' C20' 1.512(9) . ? C17' C18' 1.498(11) . ? C17' C19' 1.505(12) . ? C20' C21' 1.540(9) . ? C20' C22' 1.542(9) . ? C23' C24' 1.388(8) . ? C23' C28' 1.390(8) . ? C24' C25' 1.392(8) . ? C24' C29' 1.509(9) . ? C25' C26' 1.355(9) . ? C26' C27' 1.373(9) . ? C27' C28' 1.397(8) . ? C28' C32' 1.523(8) . ? C29' C30' 1.515(10) . ? C29' C31' 1.527(10) . ? C32' C34' 1.529(9) . ? C32' C33' 1.542(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 N2 Fe1 N3 80.1(2) . . ? N2 Fe1 N1 79.1(2) . . ? N3 Fe1 N1 159.2(2) . . ? N2 Fe1 C10 176.0(2) . . ? N3 Fe1 C10 101.7(2) . . ? N1 Fe1 C10 99.0(2) . . ? C2 N1 C11 117.9(5) . . ? C2 N1 Fe1 116.2(4) . . ? C11 N1 Fe1 125.8(4) . . ? C3 N2 C7 121.8(5) . . ? C3 N2 Fe1 119.5(4) . . ? C7 N2 Fe1 118.5(4) . . ? C8 N3 C23 117.5(5) . . ? C8 N3 Fe1 116.5(4) . . ? C23 N3 Fe1 125.9(4) . . ? N1 C2 C3 113.5(5) . . ? N1 C2 C1 124.9(6) . . ? C3 C2 C1 121.7(5) . . ? N2 C3 C4 121.2(6) . . ? N2 C3 C2 111.5(5) . . ? C4 C3 C2 127.2(6) . . ? C3 C4 C5 116.9(6) . . ? C6 C5 C4 121.2(6) . . ? C5 C6 C7 119.8(6) . . ? N2 C7 C6 119.0(5) . . ? N2 C7 C8 111.2(5) . . ? C6 C7 C8 129.7(6) . . ? N3 C8 C7 113.7(5) . . ? N3 C8 C9 124.7(5) . . ? C7 C8 C9 121.6(6) . . ? C16 C11 C12 121.3(6) . . ? C16 C11 N1 118.5(6) . . ? C12 C11 N1 119.9(6) . . ? C13 C12 C11 118.2(6) . . ? C13 C12 C17 120.5(6) . . ? C11 C12 C17 121.3(6) . . ? C14 C13 C12 121.5(7) . . ? C13 C14 C15 119.7(7) . . ? C14 C15 C16 121.6(6) . . ? C15 C16 C11 117.5(6) . . ? C15 C16 C20 120.6(6) . . ? C11 C16 C20 121.9(6) . . ? C19 C17 C12 111.8(6) . . ? C19 C17 C18 109.0(6) . . ? C12 C17 C18 111.7(6) . . ? C21 C20 C16 110.8(6) . . ? C21 C20 C22 110.6(6) . . ? C16 C20 C22 111.8(6) . . ? C24 C23 C28 121.5(5) . . ? C24 C23 N3 120.1(5) . . ? C28 C23 N3 118.3(5) . . ? C23 C24 C25 118.1(5) . . ? C23 C24 C39 120.8(6) . . ? C25 C24 C39 121.1(6) . . ? C26 C25 C24 121.9(6) . . ? C27 C26 C25 118.9(6) . . ? C26 C27 C28 121.5(6) . . ? C27 C28 C23 118.1(6) . . ? C27 C28 C32 119.0(6) . . ? C23 C28 C32 122.9(6) . . ? C34 C32 C28 113.1(7) . . ? C34 C32 C33 111.2(6) . . ? C28 C32 C33 111.2(6) . . ? C24 C39 C31 110.1(6) . . ? C24 C39 C30 112.9(6) . . ? C31 C39 C30 111.1(6) . . ? N2' Fe1' N1' 79.7(2) . . ? N2' Fe1' N3' 80.4(2) . . ? N1' Fe1' N3' 160.1(2) . . ? N2' Fe1' C10' 176.0(3) . . ? N1' Fe1' C10' 100.3(2) . . ? N3' Fe1' C10' 99.6(2) . . ? C2' N1' C11' 118.4(5) . . ? C2' N1' Fe1' 117.3(4) . . ? C11' N1' Fe1' 124.2(4) . . ? C3' N2' C7' 122.1(5) . . ? C3' N2' Fe1' 119.6(4) . . ? C7' N2' Fe1' 118.2(4) . . ? C8' N3' C23' 118.9(5) . . ? C8' N3' Fe1' 116.0(4) . . ? C23' N3' Fe1' 125.1(4) . . ? N1' C2' C3' 112.4(5) . . ? N1' C2' C1' 124.6(6) . . ? C3' C2' C1' 123.1(6) . . ? N2' C3' C4' 119.7(6) . . ? N2' C3' C2' 111.0(5) . . ? C4' C3' C2' 129.2(6) . . ? C5' C4' C3' 118.6(6) . . ? C6' C5' C4' 120.5(6) . . ? C5' C6' C7' 120.3(6) . . ? N2' C7' C6' 118.6(6) . . ? N2' C7' C8' 111.1(5) . . ? C6' C7' C8' 130.2(6) . . ? N3' C8' C7' 114.2(5) . . ? N3' C8' C9' 124.1(5) . . ? C7' C8' C9' 121.7(6) . . ? C12' C11' C16' 122.7(6) . . ? C12' C11' N1' 117.9(6) . . ? C16' C11' N1' 119.3(6) . . ? C11' C12' C13' 117.9(7) . . ? C11' C12' C17' 123.2(7) . . ? C13' C12' C17' 118.8(7) . . ? C12' C13' C14' 120.2(7) . . ? C15' C14' C13' 120.7(7) . . ? C14' C15' C16' 120.7(7) . . ? C15' C16' C11' 117.8(6) . . ? C15' C16' C20' 121.0(7) . . ? C11' C16' C20' 121.2(6) . . ? C12' C17' C18' 114.8(7) . . ? C12' C17' C19' 111.8(8) . . ? C18' C17' C19' 107.1(9) . . ? C16' C20' C21' 109.8(5) . . ? C16' C20' C22' 111.8(6) . . ? C21' C20' C22' 109.4(6) . . ? C24' C23' C28' 122.2(5) . . ? C24' C23' N3' 118.6(6) . . ? C28' C23' N3' 119.1(5) . . ? C23' C24' C25' 116.8(6) . . ? C23' C24' C29' 122.5(5) . . ? C25' C24' C29' 120.6(6) . . ? C26' C25' C24' 122.8(6) . . ? C25' C26' C27' 119.2(6) . . ? C26' C27' C28' 121.1(6) . . ? C23' C28' C27' 117.7(6) . . ? C23' C28' C32' 121.9(5) . . ? C27' C28' C32' 120.3(6) . . ? C24' C29' C30' 110.9(6) . . ? C24' C29' C31' 113.4(7) . . ? C30' C29' C31' 110.1(7) . . ? C28' C32' C34' 113.0(5) . . ? C28' C32' C33' 111.3(5) . . ? C34' C32' C33' 108.6(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 20.82 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.355 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.076 data_mwb9 _database_code_depnum_ccdc_archive 'CCDC 267324' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H65 Fe N3 Si2' _chemical_formula_weight 711.99 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' Si Si 0.0817 0.0704 '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 Pbca 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' '-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 15.8771(7) _cell_length_b 20.0007(7) _cell_length_c 26.177(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8312.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7688 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 23.12 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.138 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3088 _exptl_absorpt_coefficient_mu 0.450 _exptl_absorpt_correction_type 'semiempirical by SADABS' _exptl_absorpt_correction_T_min 0.8230 _exptl_absorpt_correction_T_max 0.9563 _exptl_absorpt_process_details ? _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 'Bruker X8 APEX II diffractometer' _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 67211 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 23.29 _reflns_number_total 5980 _reflns_number_gt 4588 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT+' _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^)+(0.0539P)^2^+6.1084P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5980 _refine_ls_number_parameters 508 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.003 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 0.98351(2) 0.259306(17) 0.112142(13) 0.02237(12) Uani 1 1 d . . . Si1 Si 1.18556(5) 0.32077(4) 0.08558(3) 0.0363(2) Uani 1 1 d . . . Si2 Si 0.95634(5) 0.21849(4) 0.24147(3) 0.0348(2) Uani 1 1 d . . . N1 N 0.92033(11) 0.35704(9) 0.10602(7) 0.0236(5) Uani 1 1 d . . . N2 N 0.96526(12) 0.27501(9) 0.03698(7) 0.0221(5) Uani 1 1 d . . . N3 N 0.98945(12) 0.15838(10) 0.07327(7) 0.0242(5) Uani 1 1 d . . . C1 C 0.89116(18) 0.45235(13) 0.04772(10) 0.0384(7) Uani 1 1 d . . . H1A H 0.8629 0.4720 0.0774 0.058 Uiso 1 1 calc R . . H1B H 0.8521 0.4512 0.0188 0.058 Uiso 1 1 calc R . . H1C H 0.9405 0.4794 0.0388 0.058 Uiso 1 1 calc R . . C2 C 0.91873(15) 0.38260(12) 0.06027(9) 0.0257(6) Uani 1 1 d . . . C3 C 0.94493(15) 0.33762(12) 0.01997(9) 0.0262(6) Uani 1 1 d . . . C4 C 0.94656(18) 0.35330(14) -0.03154(10) 0.0353(7) Uani 1 1 d . . . H4 H 0.9326(17) 0.3961(15) -0.0419(10) 0.045(8) Uiso 1 1 d . . . C5 C 0.96658(19) 0.30477(15) -0.06697(11) 0.0413(7) Uani 1 1 d . . . H5 H 0.9684(16) 0.3125(14) -0.1017(11) 0.040(8) Uiso 1 1 d . . . C6 C 0.98079(18) 0.24010(15) -0.05013(11) 0.0343(7) Uani 1 1 d . . . H6 H 0.9896(16) 0.2083(14) -0.0712(10) 0.035(8) Uiso 1 1 d . . . C7 C 0.97922(15) 0.22603(12) 0.00146(9) 0.0250(6) Uani 1 1 d . . . C8 C 0.99014(14) 0.15991(12) 0.02359(9) 0.0250(6) Uani 1 1 d . . . C9 C 0.99800(18) 0.10014(13) -0.01073(10) 0.0375(7) Uani 1 1 d . . . H9A H 0.9990 0.0593 0.0100 0.056 Uiso 1 1 calc R . . H9B H 1.0503 0.1034 -0.0305 0.056 Uiso 1 1 calc R . . H9C H 0.9498 0.0986 -0.0341 0.056 Uiso 1 1 calc R . . C10 C 1.10642(16) 0.28431(15) 0.12903(10) 0.0301(6) Uani 1 1 d . . . H10B H 1.1000(17) 0.3154(14) 0.1578(11) 0.046(8) Uiso 1 1 d . . . H10A H 1.1256(17) 0.2419(14) 0.1411(10) 0.041(8) Uiso 1 1 d . . . C11 C 1.2101(2) 0.26423(17) 0.03084(13) 0.0605(9) Uani 1 1 d . . . H11A H 1.2329 0.2220 0.0438 0.091 Uiso 1 1 calc R . . H11B H 1.2519 0.2856 0.0086 0.091 Uiso 1 1 calc R . . H11C H 1.1586 0.2555 0.0114 0.091 Uiso 1 1 calc R . . C12 C 1.28709(18) 0.33752(18) 0.12011(14) 0.0626(10) Uani 1 1 d . . . H12A H 1.2768 0.3685 0.1484 0.094 Uiso 1 1 calc R . . H12B H 1.3278 0.3574 0.0964 0.094 Uiso 1 1 calc R . . H12C H 1.3097 0.2954 0.1335 0.094 Uiso 1 1 calc R . . C13 C 1.1512(2) 0.40273(15) 0.05818(13) 0.0556(9) Uani 1 1 d . . . H13A H 1.0980 0.3967 0.0397 0.083 Uiso 1 1 calc R . . H13B H 1.1943 0.4193 0.0346 0.083 Uiso 1 1 calc R . . H13C H 1.1432 0.4351 0.0859 0.083 Uiso 1 1 calc R . . C14 C 0.92028(19) 0.22379(16) 0.17499(11) 0.0318(6) Uani 1 1 d . . . H14B H 0.880(2) 0.2432(17) 0.1748(13) 0.063(13) Uiso 1 1 d . . . H14A H 0.9069(18) 0.1810(17) 0.1672(11) 0.056(10) Uiso 1 1 d . . . C15 C 0.9705(2) 0.30191(16) 0.27157(12) 0.0523(8) Uani 1 1 d . . . H15A H 1.0199 0.3240 0.2567 0.078 Uiso 1 1 calc R . . H15B H 0.9787 0.2964 0.3084 0.078 Uiso 1 1 calc R . . H15C H 0.9203 0.3293 0.2654 0.078 Uiso 1 1 calc R . . C16 C 0.8745(2) 0.17384(17) 0.28019(11) 0.0561(9) Uani 1 1 d . . . H16A H 0.8213 0.1985 0.2785 0.084 Uiso 1 1 calc R . . H16B H 0.8931 0.1710 0.3158 0.084 Uiso 1 1 calc R . . H16C H 0.8664 0.1287 0.2665 0.084 Uiso 1 1 calc R . . C17 C 1.05730(19) 0.17093(15) 0.24701(12) 0.0524(8) Uani 1 1 d . . . H17A H 1.0520 0.1282 0.2290 0.079 Uiso 1 1 calc R . . H17B H 1.0697 0.1626 0.2831 0.079 Uiso 1 1 calc R . . H17C H 1.1031 0.1971 0.2318 0.079 Uiso 1 1 calc R . . C18 C 0.88291(15) 0.39183(12) 0.14841(9) 0.0260(6) Uani 1 1 d . . . C19 C 0.92753(16) 0.44024(12) 0.17636(9) 0.0294(6) Uani 1 1 d . . . C20 C 0.8873(2) 0.46872(14) 0.21839(10) 0.0376(7) Uani 1 1 d . . . H20 H 0.9161(16) 0.4974(13) 0.2365(10) 0.031(7) Uiso 1 1 d . . . C21 C 0.80777(19) 0.45050(15) 0.23243(11) 0.0411(7) Uani 1 1 d . . . H21 H 0.7854(18) 0.4690(15) 0.2614(11) 0.052(9) Uiso 1 1 d . . . C22 C 0.7649(2) 0.40359(15) 0.20476(11) 0.0406(7) Uani 1 1 d . . . H22 H 0.7159(18) 0.3908(14) 0.2139(10) 0.038(8) Uiso 1 1 d . . . C23 C 0.80017(15) 0.37316(13) 0.16209(10) 0.0316(6) Uani 1 1 d . . . C24 C 0.75053(17) 0.32333(14) 0.13002(11) 0.0389(7) Uani 1 1 d . . . H24 H 0.7891(16) 0.2946(13) 0.1128(9) 0.034(7) Uiso 1 1 d . . . C25 C 0.7028(2) 0.35759(16) 0.08703(13) 0.0568(9) Uani 1 1 d . . . H25A H 0.6607 0.3880 0.1015 0.085 Uiso 1 1 calc R . . H25B H 0.6745 0.3238 0.0660 0.085 Uiso 1 1 calc R . . H25C H 0.7423 0.3830 0.0658 0.085 Uiso 1 1 calc R . . C26 C 0.6896(2) 0.28034(18) 0.16115(15) 0.0674(10) Uani 1 1 d . . . H26A H 0.7203 0.2583 0.1889 0.101 Uiso 1 1 calc R . . H26B H 0.6642 0.2464 0.1389 0.101 Uiso 1 1 calc R . . H26C H 0.6452 0.3088 0.1755 0.101 Uiso 1 1 calc R . . C27 C 1.01492(18) 0.46283(14) 0.16128(11) 0.0373(7) Uani 1 1 d . . . H27 H 1.0356(15) 0.4347(13) 0.1346(10) 0.028(7) Uiso 1 1 d . . . C28 C 1.07971(18) 0.45488(16) 0.20426(11) 0.0491(8) Uani 1 1 d . . . H28A H 1.0640 0.4835 0.2331 0.074 Uiso 1 1 calc R . . H28B H 1.1355 0.4679 0.1917 0.074 Uiso 1 1 calc R . . H28C H 1.0811 0.4081 0.2155 0.074 Uiso 1 1 calc R . . C29 C 1.0149(2) 0.53558(15) 0.14349(12) 0.0568(9) Uani 1 1 d . . . H29A H 0.9728 0.5414 0.1165 0.085 Uiso 1 1 calc R . . H29B H 1.0707 0.5472 0.1303 0.085 Uiso 1 1 calc R . . H29C H 1.0010 0.5648 0.1723 0.085 Uiso 1 1 calc R . . C30 C 0.99351(16) 0.09535(12) 0.09957(9) 0.0272(6) Uani 1 1 d . . . C31 C 0.91709(17) 0.06577(13) 0.11491(10) 0.0339(6) Uani 1 1 d . . . C32 C 0.9221(2) 0.00624(14) 0.14233(11) 0.0449(8) Uani 1 1 d . . . H32 H 0.8723(18) -0.0122(14) 0.1531(11) 0.045(8) Uiso 1 1 d . . . C33 C 0.9974(2) -0.02333(16) 0.15347(12) 0.0484(9) Uani 1 1 d . . . H33 H 0.9986(16) -0.0620(15) 0.1708(11) 0.042(8) Uiso 1 1 d . . . C34 C 1.0706(2) 0.00614(14) 0.13850(11) 0.0424(7) Uani 1 1 d . . . H34 H 1.1215(18) -0.0116(14) 0.1462(10) 0.041(8) Uiso 1 1 d . . . C35 C 1.07138(17) 0.06650(13) 0.11171(9) 0.0326(6) Uani 1 1 d . . . C36 C 0.83230(17) 0.09571(15) 0.10137(12) 0.0428(7) Uani 1 1 d . . . H36 H 0.8380(15) 0.1438(13) 0.0971(9) 0.031(7) Uiso 1 1 d . . . C37 C 0.7989(2) 0.06762(19) 0.05328(13) 0.0706(10) Uani 1 1 d . . . H37A H 0.8368 0.0791 0.0250 0.106 Uiso 1 1 calc R . . H37B H 0.7429 0.0862 0.0466 0.106 Uiso 1 1 calc R . . H37C H 0.7949 0.0189 0.0563 0.106 Uiso 1 1 calc R . . C38 C 0.7651(2) 0.08669(17) 0.14275(14) 0.0642(10) Uani 1 1 d . . . H38A H 0.7537 0.0389 0.1475 0.096 Uiso 1 1 calc R . . H38B H 0.7132 0.1094 0.1323 0.096 Uiso 1 1 calc R . . H38C H 0.7853 0.1059 0.1749 0.096 Uiso 1 1 calc R . . C39 C 1.15402(18) 0.09836(16) 0.09590(11) 0.0408(7) Uani 1 1 d . . . H39A H 1.1423(15) 0.1398(13) 0.0839(9) 0.028(7) Uiso 1 1 d . . . C40 C 1.21588(19) 0.10535(18) 0.14014(13) 0.0612(9) Uani 1 1 d . . . H40A H 1.1888 0.1296 0.1682 0.092 Uiso 1 1 calc R . . H40B H 1.2657 0.1301 0.1287 0.092 Uiso 1 1 calc R . . H40C H 1.2329 0.0608 0.1519 0.092 Uiso 1 1 calc R . . C41 C 1.1964(2) 0.05997(19) 0.05251(13) 0.0687(10) Uani 1 1 d . . . H41A H 1.2113 0.0150 0.0643 0.103 Uiso 1 1 calc R . . H41B H 1.2474 0.0837 0.0418 0.103 Uiso 1 1 calc R . . H41C H 1.1575 0.0566 0.0235 0.103 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 0.0228(2) 0.0235(2) 0.0208(2) 0.00244(14) 0.00036(15) -0.00159(14) Si1 0.0291(4) 0.0378(5) 0.0419(5) -0.0040(4) 0.0070(3) -0.0082(3) Si2 0.0382(4) 0.0349(4) 0.0314(4) 0.0059(3) 0.0019(3) 0.0007(3) N1 0.0208(10) 0.0244(11) 0.0255(12) -0.0009(9) -0.0006(9) 0.0002(9) N2 0.0234(11) 0.0214(11) 0.0214(11) 0.0020(9) 0.0005(8) -0.0024(8) N3 0.0262(11) 0.0208(11) 0.0255(12) 0.0016(8) -0.0014(9) -0.0022(9) C1 0.0525(18) 0.0281(15) 0.0347(15) 0.0032(12) -0.0078(14) 0.0078(13) C2 0.0245(13) 0.0247(14) 0.0280(14) 0.0029(11) -0.0042(11) -0.0025(11) C3 0.0275(14) 0.0240(14) 0.0272(14) 0.0042(11) -0.0022(11) -0.0021(11) C4 0.0485(17) 0.0284(16) 0.0289(16) 0.0077(13) -0.0031(13) 0.0017(13) C5 0.063(2) 0.0405(19) 0.0203(16) 0.0056(13) 0.0007(14) -0.0029(14) C6 0.0448(17) 0.0334(17) 0.0247(15) -0.0043(13) 0.0021(13) -0.0014(13) C7 0.0259(13) 0.0252(14) 0.0238(13) -0.0006(11) 0.0020(11) -0.0030(11) C8 0.0226(13) 0.0264(14) 0.0262(15) -0.0026(11) 0.0009(11) -0.0032(10) C9 0.0540(18) 0.0260(15) 0.0325(16) -0.0041(12) 0.0050(13) 0.0012(13) C10 0.0282(15) 0.0295(16) 0.0326(15) 0.0000(13) -0.0001(12) -0.0029(12) C11 0.063(2) 0.058(2) 0.061(2) -0.0150(17) 0.0233(18) -0.0177(17) C12 0.0343(18) 0.073(2) 0.081(2) -0.0047(19) 0.0038(17) -0.0171(17) C13 0.0496(19) 0.052(2) 0.065(2) 0.0128(16) 0.0219(17) -0.0087(16) C14 0.0308(17) 0.0295(18) 0.0350(16) 0.0016(13) 0.0029(13) -0.0015(14) C15 0.063(2) 0.051(2) 0.0424(18) -0.0026(15) -0.0048(16) -0.0003(16) C16 0.055(2) 0.073(2) 0.0402(18) 0.0179(16) 0.0043(15) -0.0074(17) C17 0.0519(19) 0.053(2) 0.0524(19) 0.0161(16) -0.0002(16) 0.0082(16) C18 0.0316(14) 0.0222(14) 0.0243(14) 0.0017(10) 0.0007(11) 0.0063(11) C19 0.0382(15) 0.0233(14) 0.0265(14) 0.0023(11) -0.0015(12) 0.0026(11) C20 0.053(2) 0.0303(16) 0.0296(16) -0.0050(13) -0.0089(15) 0.0065(14) C21 0.0441(19) 0.0480(19) 0.0313(17) -0.0051(14) 0.0062(14) 0.0166(15) C22 0.0310(17) 0.0471(19) 0.0436(18) -0.0004(14) 0.0081(14) 0.0094(15) C23 0.0286(14) 0.0308(15) 0.0353(15) 0.0010(12) -0.0004(12) 0.0054(11) C24 0.0248(14) 0.0401(17) 0.0517(18) -0.0066(14) 0.0031(14) 0.0033(13) C25 0.0474(19) 0.059(2) 0.064(2) -0.0198(17) -0.0189(16) 0.0089(16) C26 0.0388(19) 0.076(2) 0.088(3) -0.005(2) 0.0132(18) -0.0178(17) C27 0.0458(17) 0.0336(16) 0.0326(16) -0.0079(13) 0.0025(14) -0.0078(13) C28 0.0436(18) 0.052(2) 0.0516(19) 0.0030(15) -0.0051(15) -0.0126(15) C29 0.076(2) 0.0457(19) 0.048(2) 0.0108(15) -0.0092(17) -0.0222(17) C30 0.0396(16) 0.0203(13) 0.0217(13) -0.0021(10) -0.0030(11) -0.0008(11) C31 0.0438(17) 0.0263(15) 0.0316(15) 0.0012(12) -0.0056(13) -0.0081(12) C32 0.058(2) 0.0318(17) 0.0453(18) 0.0088(14) -0.0043(16) -0.0139(16) C33 0.080(3) 0.0267(17) 0.0382(18) 0.0101(14) -0.0080(16) -0.0007(17) C34 0.060(2) 0.0321(17) 0.0355(17) 0.0012(13) -0.0103(16) 0.0163(16) C35 0.0422(16) 0.0281(15) 0.0275(14) -0.0070(11) -0.0041(12) 0.0058(12) C36 0.0366(17) 0.0350(18) 0.057(2) 0.0084(14) -0.0086(14) -0.0149(13) C37 0.069(2) 0.085(3) 0.059(2) 0.008(2) -0.0123(19) -0.020(2) C38 0.048(2) 0.059(2) 0.086(3) 0.0054(19) 0.0125(19) -0.0166(17) C39 0.0388(17) 0.0372(18) 0.0464(18) -0.0007(14) -0.0019(14) 0.0124(14) C40 0.0420(19) 0.074(2) 0.067(2) -0.0139(19) -0.0099(17) 0.0048(17) C41 0.058(2) 0.090(3) 0.058(2) -0.017(2) 0.0086(18) 0.017(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 Fe1 N2 2.0133(19) . ? Fe1 C14 2.054(3) . ? Fe1 C10 2.062(3) . ? Fe1 N1 2.2030(19) . ? Fe1 N3 2.263(2) . ? Si1 C10 1.845(3) . ? Si1 C11 1.867(3) . ? Si1 C13 1.871(3) . ? Si1 C12 1.878(3) . ? Si2 C14 1.835(3) . ? Si2 C15 1.859(3) . ? Si2 C17 1.869(3) . ? Si2 C16 1.874(3) . ? N1 C2 1.302(3) . ? N1 C18 1.438(3) . ? N2 C3 1.368(3) . ? N2 C7 1.369(3) . ? N3 C8 1.301(3) . ? N3 C30 1.438(3) . ? C1 C2 1.499(3) . ? C2 C3 1.448(3) . ? C3 C4 1.384(3) . ? C4 C5 1.380(4) . ? C5 C6 1.385(4) . ? C6 C7 1.380(4) . ? C7 C8 1.454(3) . ? C8 C9 1.501(3) . ? C18 C19 1.405(3) . ? C18 C23 1.412(3) . ? C19 C20 1.394(4) . ? C19 C27 1.512(4) . ? C20 C21 1.365(4) . ? C21 C22 1.366(4) . ? C22 C23 1.390(4) . ? C23 C24 1.523(4) . ? C24 C25 1.520(4) . ? C24 C26 1.530(4) . ? C27 C29 1.528(4) . ? C27 C28 1.533(4) . ? C30 C35 1.401(4) . ? C30 C31 1.408(4) . ? C31 C32 1.392(4) . ? C31 C36 1.516(4) . ? C32 C33 1.364(4) . ? C33 C34 1.361(4) . ? C34 C35 1.396(4) . ? C35 C39 1.516(4) . ? C36 C37 1.477(4) . ? C36 C38 1.531(4) . ? C39 C40 1.525(4) . ? C39 C41 1.527(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 N2 Fe1 C14 140.02(10) . . ? N2 Fe1 C10 107.93(9) . . ? C14 Fe1 C10 112.00(11) . . ? N2 Fe1 N1 74.03(7) . . ? C14 Fe1 N1 98.20(11) . . ? C10 Fe1 N1 103.37(10) . . ? N2 Fe1 N3 72.88(7) . . ? C14 Fe1 N3 94.13(10) . . ? C10 Fe1 N3 105.86(10) . . ? N1 Fe1 N3 141.07(7) . . ? C10 Si1 C11 112.09(14) . . ? C10 Si1 C13 112.58(13) . . ? C11 Si1 C13 107.31(16) . . ? C10 Si1 C12 111.00(14) . . ? C11 Si1 C12 107.34(16) . . ? C13 Si1 C12 106.18(16) . . ? C14 Si2 C15 112.82(15) . . ? C14 Si2 C17 111.75(15) . . ? C15 Si2 C17 108.67(15) . . ? C14 Si2 C16 108.92(14) . . ? C15 Si2 C16 106.39(15) . . ? C17 Si2 C16 108.05(14) . . ? C2 N1 C18 120.8(2) . . ? C2 N1 Fe1 115.09(15) . . ? C18 N1 Fe1 124.14(14) . . ? C3 N2 C7 118.2(2) . . ? C3 N2 Fe1 119.68(15) . . ? C7 N2 Fe1 121.93(15) . . ? C8 N3 C30 119.9(2) . . ? C8 N3 Fe1 115.40(16) . . ? C30 N3 Fe1 124.66(15) . . ? N1 C2 C3 114.9(2) . . ? N1 C2 C1 124.9(2) . . ? C3 C2 C1 120.2(2) . . ? N2 C3 C4 121.3(2) . . ? N2 C3 C2 113.5(2) . . ? C4 C3 C2 125.1(2) . . ? C5 C4 C3 120.0(3) . . ? C4 C5 C6 118.7(3) . . ? C7 C6 C5 119.9(3) . . ? N2 C7 C6 121.5(2) . . ? N2 C7 C8 113.5(2) . . ? C6 C7 C8 125.0(2) . . ? N3 C8 C7 114.8(2) . . ? N3 C8 C9 125.5(2) . . ? C7 C8 C9 119.7(2) . . ? Si1 C10 Fe1 127.45(14) . . ? Si2 C14 Fe1 128.83(16) . . ? C19 C18 C23 121.3(2) . . ? C19 C18 N1 121.8(2) . . ? C23 C18 N1 116.9(2) . . ? C20 C19 C18 117.5(2) . . ? C20 C19 C27 120.3(2) . . ? C18 C19 C27 122.2(2) . . ? C21 C20 C19 121.8(3) . . ? C20 C21 C22 120.1(3) . . ? C21 C22 C23 121.8(3) . . ? C22 C23 C18 117.6(2) . . ? C22 C23 C24 121.4(2) . . ? C18 C23 C24 121.0(2) . . ? C25 C24 C23 111.8(2) . . ? C25 C24 C26 109.4(3) . . ? C23 C24 C26 113.7(2) . . ? C19 C27 C29 111.3(2) . . ? C19 C27 C28 113.2(2) . . ? C29 C27 C28 108.8(2) . . ? C35 C30 C31 121.5(2) . . ? C35 C30 N3 120.6(2) . . ? C31 C30 N3 117.8(2) . . ? C32 C31 C30 117.2(3) . . ? C32 C31 C36 120.6(3) . . ? C30 C31 C36 122.2(2) . . ? C33 C32 C31 122.1(3) . . ? C34 C33 C32 119.9(3) . . ? C33 C34 C35 121.8(3) . . ? C34 C35 C30 117.5(3) . . ? C34 C35 C39 120.5(3) . . ? C30 C35 C39 121.9(2) . . ? C37 C36 C31 111.6(3) . . ? C37 C36 C38 107.9(3) . . ? C31 C36 C38 114.0(3) . . ? C35 C39 C40 112.9(3) . . ? C35 C39 C41 111.9(3) . . ? C40 C39 C41 109.1(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.762 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.046 data_rt1 _database_code_depnum_ccdc_archive 'CCDC 267325' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H45 Cl Fe N3 O' _chemical_formula_weight 591.02 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 13.1161(5) _cell_length_b 19.2048(8) _cell_length_c 13.5204(6) _cell_angle_alpha 90.00 _cell_angle_beta 115.1460(10) _cell_angle_gamma 90.00 _cell_volume 3082.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1260 _exptl_absorpt_coefficient_mu 0.606 _exptl_absorpt_correction_type 'semiempirical by SADABS' _exptl_absorpt_correction_T_min 0.8392 _exptl_absorpt_correction_T_max 0.9419 _exptl_absorpt_process_details ? _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 'Bruker 1K 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 25123 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7615 _reflns_number_gt 5271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0567P)^2^+2.5255P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7615 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.269 _refine_ls_shift/su_mean 0.012 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 0.20529(3) 0.333974(18) 0.33012(3) 0.02226(11) Uani 1 1 d . . . Cl1 Cl 0.14755(7) 0.44487(4) 0.27942(7) 0.0455(2) Uani 1 1 d . . . O1 O 0.36798(17) 0.35405(12) 0.47184(17) 0.0438(5) Uani 1 1 d . . . N1 N 0.10297(17) 0.30356(11) 0.41479(17) 0.0249(4) Uani 1 1 d . . . N2 N 0.18434(17) 0.23069(11) 0.30672(16) 0.0247(5) Uani 1 1 d . . . N3 N 0.28668(18) 0.30671(11) 0.22195(17) 0.0263(5) Uani 1 1 d . . . C1 C 0.0173(3) 0.20587(18) 0.4718(3) 0.0439(8) Uani 1 1 d . . . H1C H 0.009(3) 0.158(2) 0.466(3) 0.065(12) Uiso 1 1 d . . . H1B H 0.034(3) 0.227(2) 0.540(3) 0.069(12) Uiso 1 1 d . . . H1A H -0.067(4) 0.221(3) 0.432(4) 0.101(16) Uiso 1 1 d . . . C2 C 0.0855(2) 0.23634(14) 0.4168(2) 0.0271(5) Uani 1 1 d . . . C3 C 0.1342(2) 0.19311(14) 0.3608(2) 0.0269(5) Uani 1 1 d . . . C4 C 0.1321(2) 0.12092(14) 0.3574(2) 0.0328(6) Uani 1 1 d . . . H4 H 0.098(2) 0.0966(16) 0.396(2) 0.036(8) Uiso 1 1 d . . . C5 C 0.1819(3) 0.08544(15) 0.2990(3) 0.0382(7) Uani 1 1 d . . . H5 H 0.183(2) 0.0359(16) 0.296(2) 0.032(8) Uiso 1 1 d . . . C6 C 0.2310(2) 0.12322(15) 0.2435(2) 0.0322(6) Uani 1 1 d . . . H6 H 0.265(3) 0.1043(18) 0.202(3) 0.048(9) Uiso 1 1 d . . . C7 C 0.2318(2) 0.19543(13) 0.2486(2) 0.0251(5) Uani 1 1 d . . . C8 C 0.2820(2) 0.24119(14) 0.1959(2) 0.0259(5) Uani 1 1 d . . . C9 C 0.3216(3) 0.21167(18) 0.1157(3) 0.0389(7) Uani 1 1 d . . . H9C H 0.262(3) 0.1873(18) 0.060(3) 0.048(9) Uiso 1 1 d . . . H9B H 0.346(3) 0.2475(18) 0.081(3) 0.042(9) Uiso 1 1 d . . . H9A H 0.384(4) 0.182(2) 0.149(4) 0.076(13) Uiso 1 1 d . . . C10 C 0.0430(2) 0.34969(13) 0.4556(2) 0.0272(6) Uani 1 1 d . . . C11 C -0.0644(2) 0.37222(14) 0.3841(2) 0.0321(6) Uani 1 1 d . . . C12 C -0.1213(3) 0.41609(16) 0.4264(3) 0.0413(7) Uani 1 1 d . . . H12 H -0.194(3) 0.4285(17) 0.381(3) 0.041(9) Uiso 1 1 d . . . C13 C -0.0724(3) 0.43740(16) 0.5344(3) 0.0439(8) Uani 1 1 d . . . H13 H -0.114(3) 0.4650(19) 0.555(3) 0.055(10) Uiso 1 1 d . . . C14 C 0.0342(3) 0.41551(16) 0.6023(3) 0.0411(7) Uani 1 1 d . . . H14 H 0.069(3) 0.4288(18) 0.673(3) 0.049(10) Uiso 1 1 d . . . C15 C 0.0942(2) 0.37103(14) 0.5654(2) 0.0329(6) Uani 1 1 d . . . C16 C -0.1177(3) 0.34999(19) 0.2660(3) 0.0464(8) Uani 1 1 d . . . H16B H -0.073(3) 0.328(2) 0.248(3) 0.065(12) Uiso 1 1 d . . . H16A H -0.172(4) 0.314(3) 0.258(4) 0.093(15) Uiso 1 1 d . . . C17 C -0.1769(4) 0.4056(2) 0.1850(3) 0.0721(12) Uani 1 1 d . . . H17A H -0.2084 0.3858 0.1112 0.108 Uiso 1 1 calc R . . H17B H -0.1234 0.4426 0.1902 0.108 Uiso 1 1 calc R . . H17C H -0.2378 0.4250 0.2003 0.108 Uiso 1 1 calc R . . C19 C 0.2718(5) 0.3845(3) 0.7457(3) 0.0764(14) Uani 1 1 d . . . H19C H 0.230(3) 0.377(2) 0.788(4) 0.069(13) Uiso 1 1 d . . . H19B H 0.354(5) 0.372(3) 0.789(5) 0.12(2) Uiso 1 1 d . . . H19A H 0.268(4) 0.434(3) 0.730(4) 0.089(16) Uiso 1 1 d . . . C18 C 0.2113(3) 0.34622(19) 0.6377(3) 0.0444(8) Uani 1 1 d . . . H18B H 0.209(3) 0.2968(18) 0.651(3) 0.041(9) Uiso 1 1 d . . . H18A H 0.256(3) 0.3518(18) 0.595(3) 0.052(10) Uiso 1 1 d . . . C20 C 0.3345(3) 0.35575(15) 0.1732(2) 0.0359(7) Uani 1 1 d . . . C21 C 0.4504(3) 0.36843(18) 0.2240(3) 0.0489(9) Uani 1 1 d . . . C22 C 0.4913(5) 0.4184(2) 0.1742(5) 0.0769(16) Uani 1 1 d . . . H22 H 0.564(3) 0.4230(19) 0.207(3) 0.048(11) Uiso 1 1 d . . . C23 C 0.4237(7) 0.4517(2) 0.0809(6) 0.099(2) Uani 1 1 d . . . H23 H 0.449(4) 0.483(3) 0.050(4) 0.106(17) Uiso 1 1 d . . . C24 C 0.3102(6) 0.4375(2) 0.0333(4) 0.0787(17) Uani 1 1 d . . . H24 H 0.267(3) 0.4567(19) -0.023(3) 0.043(10) Uiso 1 1 d . . . C25 C 0.2615(4) 0.38983(16) 0.0771(3) 0.0495(9) Uani 1 1 d . . . C26 C 0.5299(3) 0.3300(3) 0.3243(3) 0.0598(11) Uani 1 1 d . . . H26B H 0.488(3) 0.305(2) 0.357(3) 0.072(12) Uiso 1 1 d . . . H26A H 0.575(4) 0.364(2) 0.369(4) 0.086(15) Uiso 1 1 d . . . C27 C 0.6033(4) 0.2774(3) 0.3019(4) 0.0651(11) Uani 1 1 d . . . H27C H 0.661(4) 0.258(2) 0.365(4) 0.072(13) Uiso 1 1 d . . . H27B H 0.641(5) 0.301(3) 0.266(5) 0.12(2) Uiso 1 1 d . . . H27A H 0.563(4) 0.239(3) 0.251(4) 0.109(18) Uiso 1 1 d . . . C28 C 0.1378(4) 0.3739(2) 0.0264(3) 0.0593(11) Uani 1 1 d . . . H28A H 0.113(3) 0.3798(17) 0.081(3) 0.045(9) Uiso 1 1 d . . . H28A' H 0.127(3) 0.323(2) 0.007(3) 0.073(13) Uiso 1 1 d . . . C29 C 0.0624(5) 0.4191(3) -0.0680(4) 0.116(2) Uani 1 1 d . . . H29A H -0.0158 0.4034 -0.0937 0.174 Uiso 1 1 calc R . . H29B H 0.0858 0.4155 -0.1276 0.174 Uiso 1 1 calc R . . H29C H 0.0683 0.4676 -0.0438 0.174 Uiso 1 1 calc R . . C30 C 0.4132(3) 0.4230(2) 0.4868(4) 0.0734(13) Uani 1 1 d . . . H30A H 0.3847 0.4469 0.4152 0.088 Uiso 1 1 calc R . . H30B H 0.4963 0.4204 0.5160 0.088 Uiso 1 1 calc R . . C31 C 0.3817(6) 0.4647(3) 0.5640(6) 0.088(2) Uani 1 1 d . . . H31C H 0.420(4) 0.443(3) 0.644(4) 0.097(18) Uiso 1 1 d . . . H31B H 0.314(3) 0.4639(19) 0.542(3) 0.047(11) Uiso 1 1 d . . . H31A H 0.416(5) 0.506(3) 0.575(5) 0.13(2) Uiso 1 1 d . . . C32 C 0.4426(4) 0.3101(3) 0.5552(3) 0.0787(15) Uani 1 1 d . . . H32A H 0.5196 0.3164 0.5605 0.094 Uiso 1 1 calc R . . H32B H 0.4434 0.3245 0.6259 0.094 Uiso 1 1 calc R . . C33 C 0.4142(4) 0.2401(2) 0.5381(3) 0.0821(14) Uani 1 1 d . . . H33A H 0.4689 0.2126 0.5985 0.123 Uiso 1 1 calc R . . H33B H 0.4150 0.2250 0.4692 0.123 Uiso 1 1 calc R . . H33C H 0.3388 0.2331 0.5347 0.123 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 0.02688(18) 0.01849(18) 0.02347(18) 0.00034(15) 0.01267(14) -0.00043(15) Cl1 0.0692(5) 0.0279(4) 0.0557(5) 0.0158(3) 0.0422(4) 0.0186(4) O1 0.0336(11) 0.0485(13) 0.0373(11) -0.0126(10) 0.0036(9) 0.0061(9) N1 0.0281(11) 0.0236(11) 0.0248(10) 0.0005(9) 0.0129(9) -0.0022(9) N2 0.0263(11) 0.0223(11) 0.0241(11) 0.0012(8) 0.0094(9) 0.0009(8) N3 0.0336(12) 0.0241(11) 0.0244(11) 0.0004(9) 0.0155(9) -0.0002(9) C1 0.064(2) 0.0308(18) 0.054(2) -0.0033(15) 0.0414(19) -0.0150(16) C2 0.0291(13) 0.0263(14) 0.0268(13) 0.0030(10) 0.0128(11) -0.0025(11) C3 0.0305(13) 0.0223(13) 0.0258(13) 0.0029(10) 0.0100(11) -0.0011(10) C4 0.0388(15) 0.0238(14) 0.0355(15) 0.0053(12) 0.0155(13) -0.0006(12) C5 0.0473(17) 0.0187(14) 0.0474(18) 0.0014(12) 0.0188(14) 0.0029(12) C6 0.0347(15) 0.0261(15) 0.0333(14) -0.0020(12) 0.0121(12) 0.0062(12) C7 0.0233(12) 0.0246(13) 0.0241(12) -0.0003(10) 0.0069(10) 0.0035(10) C8 0.0255(12) 0.0264(14) 0.0251(12) -0.0014(10) 0.0102(10) 0.0022(10) C9 0.0463(18) 0.0352(17) 0.0446(18) -0.0112(14) 0.0283(16) -0.0026(15) C10 0.0379(14) 0.0211(13) 0.0315(13) -0.0001(10) 0.0232(12) -0.0060(11) C11 0.0356(14) 0.0247(14) 0.0417(16) -0.0013(12) 0.0220(13) -0.0038(12) C12 0.0433(18) 0.0311(16) 0.062(2) 0.0027(15) 0.0345(17) 0.0005(14) C13 0.069(2) 0.0243(15) 0.064(2) -0.0021(14) 0.053(2) -0.0011(15) C14 0.070(2) 0.0290(16) 0.0395(17) -0.0035(13) 0.0378(17) -0.0085(15) C15 0.0478(16) 0.0257(14) 0.0329(14) 0.0008(11) 0.0245(13) -0.0078(12) C16 0.0423(18) 0.046(2) 0.0442(18) -0.0061(15) 0.0119(15) 0.0043(16) C17 0.076(3) 0.075(3) 0.049(2) 0.005(2) 0.012(2) 0.026(2) C19 0.090(4) 0.092(4) 0.032(2) -0.013(2) 0.012(2) 0.001(3) C18 0.057(2) 0.044(2) 0.0311(15) -0.0009(14) 0.0181(15) -0.0047(16) C20 0.0598(18) 0.0257(14) 0.0396(16) -0.0079(12) 0.0379(15) -0.0064(13) C21 0.067(2) 0.0432(19) 0.063(2) -0.0275(17) 0.054(2) -0.0219(17) C22 0.109(4) 0.048(2) 0.133(4) -0.042(3) 0.109(4) -0.036(3) C23 0.209(7) 0.024(2) 0.161(6) -0.007(3) 0.173(6) -0.009(3) C24 0.174(6) 0.031(2) 0.087(3) 0.016(2) 0.109(4) 0.024(3) C25 0.102(3) 0.0256(16) 0.0424(18) 0.0011(13) 0.051(2) 0.0100(17) C26 0.0392(18) 0.097(3) 0.056(2) -0.032(2) 0.0326(17) -0.023(2) C27 0.069(3) 0.074(3) 0.059(3) -0.014(2) 0.034(2) -0.004(2) C28 0.091(3) 0.051(2) 0.0301(17) 0.0049(16) 0.0201(19) 0.023(2) C29 0.139(5) 0.147(5) 0.077(3) 0.068(4) 0.059(3) 0.082(4) C30 0.050(2) 0.088(3) 0.092(3) -0.053(3) 0.040(2) -0.039(2) C31 0.096(4) 0.075(4) 0.122(5) -0.061(4) 0.074(4) -0.050(3) C32 0.078(3) 0.104(4) 0.0339(19) -0.007(2) 0.0039(19) 0.045(3) C33 0.118(4) 0.061(3) 0.038(2) 0.0099(19) 0.005(2) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N2 2.009(2) . ? Fe1 N1 2.181(2) . ? Fe1 N3 2.209(2) . ? Fe1 O1 2.213(2) . ? Fe1 Cl1 2.2668(8) . ? O1 C32 1.415(4) . ? O1 C30 1.429(5) . ? N1 C2 1.313(3) . ? N1 C10 1.441(3) . ? N2 C7 1.371(3) . ? N2 C3 1.377(3) . ? N3 C8 1.301(3) . ? N3 C20 1.438(3) . ? C1 C2 1.503(4) . ? C2 C3 1.443(4) . ? C3 C4 1.387(4) . ? C4 C5 1.398(4) . ? C5 C6 1.384(4) . ? C6 C7 1.388(4) . ? C7 C8 1.453(4) . ? C8 C9 1.499(4) . ? C10 C11 1.396(4) . ? C10 C15 1.405(4) . ? C11 C12 1.398(4) . ? C11 C16 1.507(4) . ? C12 C13 1.384(5) . ? C13 C14 1.372(5) . ? C14 C15 1.390(4) . ? C15 C18 1.505(4) . ? C16 C17 1.490(5) . ? C19 C18 1.521(5) . ? C20 C21 1.397(5) . ? C20 C25 1.406(5) . ? C21 C22 1.403(5) . ? C21 C26 1.506(6) . ? C22 C23 1.354(8) . ? C23 C24 1.374(9) . ? C24 C25 1.385(5) . ? C25 C28 1.501(6) . ? C26 C27 1.513(6) . ? C28 C29 1.513(5) . ? C30 C31 1.507(6) . ? C32 C33 1.389(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Fe1 N1 75.22(8) . . ? N2 Fe1 N3 74.57(8) . . ? N1 Fe1 N3 149.56(8) . . ? N2 Fe1 O1 108.99(8) . . ? N1 Fe1 O1 100.03(8) . . ? N3 Fe1 O1 93.16(8) . . ? N2 Fe1 Cl1 150.96(6) . . ? N1 Fe1 Cl1 102.08(6) . . ? N3 Fe1 Cl1 102.46(6) . . ? O1 Fe1 Cl1 99.99(6) . . ? C32 O1 C30 109.5(3) . . ? C32 O1 Fe1 132.2(3) . . ? C30 O1 Fe1 118.3(2) . . ? C2 N1 C10 117.9(2) . . ? C2 N1 Fe1 115.20(17) . . ? C10 N1 Fe1 126.43(16) . . ? C7 N2 C3 118.8(2) . . ? C7 N2 Fe1 120.85(17) . . ? C3 N2 Fe1 119.88(17) . . ? C8 N3 C20 119.3(2) . . ? C8 N3 Fe1 115.35(17) . . ? C20 N3 Fe1 125.19(17) . . ? N1 C2 C3 115.8(2) . . ? N1 C2 C1 122.6(3) . . ? C3 C2 C1 121.6(2) . . ? N2 C3 C4 120.9(2) . . ? N2 C3 C2 113.3(2) . . ? C4 C3 C2 125.8(2) . . ? C3 C4 C5 119.9(3) . . ? C6 C5 C4 119.2(3) . . ? C5 C6 C7 119.5(3) . . ? N2 C7 C6 121.7(2) . . ? N2 C7 C8 113.1(2) . . ? C6 C7 C8 125.1(2) . . ? N3 C8 C7 115.6(2) . . ? N3 C8 C9 124.8(3) . . ?