# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email larryque@umn.edu _publ_contact_author_name 'Aidan McDonald' loop_ _publ_author_name 'Aidan McDonald' 'Yisong Guo' 'Van Vu' 'Emile Bominaar' 'Eckard Munck' 'Lawrence Que Junior' data_10017a _database_code_depnum_ccdc_archive 'CCDC 857970' #TrackingRef '3(b)Cl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 10017a _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 Cl Fe N3 O4, C24 H20 P, 2(C H2 Cl2)' _chemical_formula_sum 'C45 H45 Cl5 Fe N3 O4 P' _chemical_formula_weight 955.91 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' P P 0.1023 0.0942 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.234(5) _cell_length_b 14.717(3) _cell_length_c 16.801(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.866(3) _cell_angle_gamma 90.00 _cell_volume 4526.4(18) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2936 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 24.81 _exptl_crystal_description Plate _exptl_crystal_colour Red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1976 _exptl_absorpt_coefficient_mu 0.709 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7408 _exptl_absorpt_correction_T_max 0.9790 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details 'Dr. A. McDonald / Prof. L. Que' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43784 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.11 _diffrn_reflns_theta_max 25.06 _reflns_number_total 7989 _reflns_number_gt 5338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0883P)^2^+12.5424P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7989 _refine_ls_number_parameters 533 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1109 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1973 _refine_ls_wR_factor_gt 0.1669 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.78165(4) 0.76298(5) 0.71950(4) 0.0257(2) Uani 1 1 d . . . Cl1 Cl 0.68950(8) 0.84956(10) 0.74365(9) 0.0426(4) Uani 1 1 d . . . N1 N 0.8609(2) 0.6812(3) 0.6740(2) 0.0255(9) Uani 1 1 d . . . C1 C 0.9277(3) 0.6740(4) 0.7452(3) 0.0285(11) Uani 1 1 d . . . H1A H 0.9635 0.7191 0.7378 0.034 Uiso 1 1 calc R . . H1B H 0.9490 0.6129 0.7446 0.034 Uiso 1 1 calc R . . C2 C 0.9165(3) 0.6896(3) 0.8321(3) 0.0241(10) Uani 1 1 d . . . O1 O 0.96158(19) 0.6569(2) 0.8925(2) 0.0309(8) Uani 1 1 d . . . O2 O 0.86129(19) 0.7356(2) 0.83257(19) 0.0291(8) Uani 1 1 d . . . C3 C 0.8262(3) 0.5927(4) 0.6480(3) 0.0301(12) Uani 1 1 d . . . H3A H 0.8643 0.5450 0.6623 0.036 Uiso 1 1 calc R . . H3B H 0.8040 0.5927 0.5865 0.036 Uiso 1 1 calc R . . C4 C 0.7665(3) 0.5680(4) 0.6887(3) 0.0271(11) Uani 1 1 d . . . O3 O 0.7437(2) 0.4899(2) 0.6785(2) 0.0384(9) Uani 1 1 d . . . O4 O 0.74467(19) 0.6297(2) 0.7269(2) 0.0307(8) Uani 1 1 d . . . C5 C 0.8670(3) 0.7398(4) 0.6022(3) 0.0273(11) Uani 1 1 d . . . C6 C 0.8900(3) 0.8342(4) 0.6378(3) 0.0292(11) Uani 1 1 d . . . C7 C 0.9364(3) 0.8908(4) 0.6126(3) 0.0369(13) Uani 1 1 d . . . H7A H 0.9602 0.8700 0.5741 0.044 Uiso 1 1 calc R . . C8 C 0.9477(3) 0.9775(4) 0.6437(3) 0.0441(15) Uani 1 1 d . . . H8A H 0.9802 1.0170 0.6277 0.053 Uiso 1 1 calc R . . C9 C 0.9115(4) 1.0073(4) 0.6986(4) 0.0478(16) Uani 1 1 d . . . H9A H 0.9176 1.0676 0.7198 0.057 Uiso 1 1 calc R . . C10 C 0.8664(3) 0.9471(4) 0.7215(3) 0.0400(14) Uani 1 1 d . . . H10A H 0.8420 0.9668 0.7597 0.048 Uiso 1 1 calc R . . N2 N 0.8554(2) 0.8624(3) 0.6925(2) 0.0308(10) Uani 1 1 d . . . C11 C 0.7881(3) 0.7545(3) 0.5445(3) 0.0278(11) Uani 1 1 d . . . C12 C 0.7704(3) 0.7669(4) 0.4578(3) 0.0345(13) Uani 1 1 d . . . H12A H 0.8066 0.7609 0.4304 0.041 Uiso 1 1 calc R . . C13 C 0.7000(3) 0.7879(4) 0.4136(3) 0.0431(15) Uani 1 1 d . . . H13A H 0.6873 0.7986 0.3551 0.052 Uiso 1 1 calc R . . C14 C 0.6482(3) 0.7936(4) 0.4529(3) 0.0440(15) Uani 1 1 d . . . H14A H 0.5989 0.8065 0.4224 0.053 Uiso 1 1 calc R . . C15 C 0.6688(3) 0.7800(4) 0.5385(3) 0.0391(14) Uani 1 1 d . . . H15A H 0.6325 0.7835 0.5660 0.047 Uiso 1 1 calc R . . N3 N 0.7369(2) 0.7625(3) 0.5836(2) 0.0303(10) Uani 1 1 d . . . C16 C 0.9140(3) 0.6982(4) 0.5509(3) 0.0393(14) Uani 1 1 d . . . H16A H 0.8862 0.6462 0.5193 0.047 Uiso 1 1 calc R . . H16B H 0.9171 0.7443 0.5092 0.047 Uiso 1 1 calc R . . C17 C 0.9888(3) 0.6661(5) 0.5927(4) 0.0485(16) Uani 1 1 d . . . H17A H 0.9873 0.6146 0.6301 0.058 Uiso 1 1 calc R . . H17B H 1.0176 0.7156 0.6275 0.058 Uiso 1 1 calc R . . C18 C 1.0267(4) 0.6351(5) 0.5276(4) 0.0570(19) Uani 1 1 d . . . H18A H 0.9968 0.5871 0.4918 0.068 Uiso 1 1 calc R . . H18B H 1.0292 0.6872 0.4913 0.068 Uiso 1 1 calc R . . C19 C 1.1006(5) 0.6002(5) 0.5671(5) 0.071(2) Uani 1 1 d . . . H19A H 1.1233 0.5856 0.5239 0.106 Uiso 1 1 calc R . . H19B H 1.0980 0.5452 0.5990 0.106 Uiso 1 1 calc R . . H19C H 1.1297 0.6464 0.6048 0.106 Uiso 1 1 calc R . . P1 P 0.33535(7) 0.82712(8) 0.60441(7) 0.0239(3) Uani 1 1 d . . . C20 C 0.3673(3) 0.8693(4) 0.5214(3) 0.0320(12) Uani 1 1 d . . . C21 C 0.4182(3) 0.8218(4) 0.4947(4) 0.0443(15) Uani 1 1 d . . . H21A H 0.4368 0.7655 0.5202 0.053 Uiso 1 1 calc R . . C22 C 0.4419(4) 0.8564(5) 0.4307(4) 0.0550(18) Uani 1 1 d . . . H22A H 0.4756 0.8227 0.4112 0.066 Uiso 1 1 calc R . . C23 C 0.4173(4) 0.9383(5) 0.3957(4) 0.0567(18) Uani 1 1 d . . . H23A H 0.4367 0.9640 0.3550 0.068 Uiso 1 1 calc R . . C24 C 0.3653(5) 0.9830(5) 0.4189(4) 0.070(2) Uani 1 1 d . . . H24A H 0.3457 1.0379 0.3912 0.084 Uiso 1 1 calc R . . C25 C 0.3400(4) 0.9504(4) 0.4823(4) 0.0553(18) Uani 1 1 d . . . H25A H 0.3042 0.9833 0.4989 0.066 Uiso 1 1 calc R . . C26 C 0.3259(3) 0.7065(3) 0.5957(3) 0.0273(11) Uani 1 1 d . . . C27 C 0.3329(3) 0.6557(4) 0.6674(3) 0.0388(14) Uani 1 1 d . . . H27A H 0.3455 0.6848 0.7204 0.047 Uiso 1 1 calc R . . C28 C 0.3218(4) 0.5636(4) 0.6620(4) 0.0510(17) Uani 1 1 d . . . H28A H 0.3265 0.5292 0.7113 0.061 Uiso 1 1 calc R . . C29 C 0.3036(3) 0.5205(4) 0.5854(4) 0.0461(15) Uani 1 1 d . . . H29A H 0.2963 0.4566 0.5822 0.055 Uiso 1 1 calc R . . C30 C 0.2962(3) 0.5699(4) 0.5140(4) 0.0440(15) Uani 1 1 d . . . H30A H 0.2837 0.5401 0.4613 0.053 Uiso 1 1 calc R . . C31 C 0.3068(3) 0.6626(4) 0.5186(3) 0.0385(13) Uani 1 1 d . . . H31A H 0.3010 0.6967 0.4690 0.046 Uiso 1 1 calc R . . C32 C 0.2485(3) 0.8784(3) 0.5940(3) 0.0249(11) Uani 1 1 d . . . C33 C 0.2443(3) 0.9659(3) 0.6226(3) 0.0281(11) Uani 1 1 d . . . H33A H 0.2876 0.9968 0.6533 0.034 Uiso 1 1 calc R . . C34 C 0.1771(3) 1.0086(4) 0.6065(3) 0.0295(12) Uani 1 1 d . . . H34A H 0.1740 1.0686 0.6258 0.035 Uiso 1 1 calc R . . C35 C 0.1153(3) 0.9627(4) 0.5623(3) 0.0340(13) Uani 1 1 d . . . H35A H 0.0692 0.9915 0.5512 0.041 Uiso 1 1 calc R . . C36 C 0.1188(3) 0.8756(4) 0.5335(3) 0.0403(14) Uani 1 1 d . . . H36A H 0.0753 0.8451 0.5027 0.048 Uiso 1 1 calc R . . C37 C 0.1849(3) 0.8330(4) 0.5493(3) 0.0329(12) Uani 1 1 d . . . H37A H 0.1875 0.7728 0.5298 0.039 Uiso 1 1 calc R . . C38 C 0.3994(3) 0.8528(3) 0.7043(3) 0.0238(10) Uani 1 1 d . . . C39 C 0.4738(3) 0.8496(4) 0.7155(3) 0.0319(12) Uani 1 1 d . . . H39A H 0.4907 0.8377 0.6690 0.038 Uiso 1 1 calc R . . C40 C 0.5237(3) 0.8634(4) 0.7937(3) 0.0396(14) Uani 1 1 d . . . H40A H 0.5747 0.8605 0.8012 0.048 Uiso 1 1 calc R . . C41 C 0.4983(3) 0.8815(4) 0.8611(3) 0.0361(13) Uani 1 1 d . . . H41A H 0.5322 0.8911 0.9150 0.043 Uiso 1 1 calc R . . C42 C 0.4257(3) 0.8856(4) 0.8508(3) 0.0327(12) Uani 1 1 d . . . H42A H 0.4094 0.8984 0.8975 0.039 Uiso 1 1 calc R . . C43 C 0.3748(3) 0.8714(3) 0.7727(3) 0.0280(11) Uani 1 1 d . . . H43A H 0.3240 0.8744 0.7659 0.034 Uiso 1 1 calc R . . C44 C 0.5810(3) 0.6250(4) 0.6869(3) 0.0433(14) Uani 1 1 d . . . H44A H 0.6228 0.5837 0.6921 0.052 Uiso 1 1 calc R . . H44B H 0.6000 0.6879 0.6962 0.052 Uiso 1 1 calc R . . Cl2 Cl 0.51887(13) 0.61601(13) 0.58569(10) 0.0756(6) Uani 1 1 d . . . Cl3 Cl 0.53944(11) 0.59722(12) 0.76294(11) 0.0645(5) Uani 1 1 d . . . C45 C 0.8444(5) 0.3183(6) 0.7243(5) 0.081(3) Uani 1 1 d . . . H45A H 0.8726 0.3176 0.7845 0.097 Uiso 1 1 calc R . . H45B H 0.8139 0.3738 0.7133 0.097 Uiso 1 1 calc R . . Cl4 Cl 0.90558(13) 0.3219(2) 0.66440(15) 0.1020(9) Uani 1 1 d . . . Cl5 Cl 0.78773(16) 0.22269(17) 0.70106(17) 0.1017(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0340(4) 0.0322(4) 0.0156(4) 0.0024(3) 0.0145(3) 0.0026(3) Cl1 0.0607(9) 0.0375(8) 0.0417(8) 0.0104(6) 0.0334(7) 0.0154(7) N1 0.034(2) 0.034(2) 0.0126(19) 0.0043(17) 0.0134(17) -0.0014(19) C1 0.032(3) 0.041(3) 0.016(2) 0.005(2) 0.013(2) 0.007(2) C2 0.032(3) 0.028(3) 0.017(2) -0.003(2) 0.013(2) -0.004(2) O1 0.039(2) 0.042(2) 0.0120(17) -0.0009(15) 0.0092(15) -0.0034(17) O2 0.034(2) 0.042(2) 0.0134(16) -0.0013(15) 0.0107(14) 0.0035(17) C3 0.037(3) 0.035(3) 0.023(3) 0.000(2) 0.016(2) 0.001(2) C4 0.041(3) 0.033(3) 0.008(2) 0.003(2) 0.009(2) 0.000(2) O3 0.057(3) 0.035(2) 0.028(2) -0.0027(17) 0.0213(18) -0.0105(19) O4 0.039(2) 0.035(2) 0.0229(18) 0.0055(16) 0.0162(16) 0.0015(16) C5 0.036(3) 0.038(3) 0.012(2) 0.003(2) 0.013(2) 0.001(2) C6 0.029(3) 0.043(3) 0.017(2) 0.008(2) 0.009(2) 0.001(2) C7 0.043(3) 0.043(3) 0.029(3) 0.007(2) 0.017(2) -0.008(3) C8 0.048(4) 0.054(4) 0.031(3) 0.007(3) 0.012(3) -0.017(3) C9 0.060(4) 0.040(3) 0.037(3) -0.005(3) 0.006(3) -0.017(3) C10 0.057(4) 0.039(3) 0.027(3) -0.004(2) 0.017(3) -0.010(3) N2 0.040(3) 0.036(3) 0.018(2) 0.0015(18) 0.0111(19) 0.000(2) C11 0.041(3) 0.028(3) 0.015(2) 0.001(2) 0.010(2) -0.003(2) C12 0.055(4) 0.038(3) 0.014(2) 0.000(2) 0.016(2) 0.001(3) C13 0.053(4) 0.056(4) 0.014(3) 0.000(2) 0.002(3) -0.005(3) C14 0.039(3) 0.061(4) 0.022(3) 0.002(3) -0.005(2) -0.006(3) C15 0.032(3) 0.054(4) 0.033(3) 0.005(3) 0.011(2) -0.002(3) N3 0.036(2) 0.038(3) 0.020(2) 0.0020(18) 0.0134(19) -0.002(2) C16 0.051(4) 0.051(4) 0.025(3) 0.011(3) 0.025(3) 0.010(3) C17 0.052(4) 0.066(4) 0.036(3) 0.007(3) 0.025(3) 0.003(3) C18 0.091(5) 0.051(4) 0.051(4) 0.007(3) 0.056(4) 0.006(4) C19 0.099(6) 0.069(5) 0.065(5) 0.007(4) 0.056(5) 0.014(5) P1 0.0325(7) 0.0242(7) 0.0149(6) -0.0004(5) 0.0071(5) 0.0018(5) C20 0.047(3) 0.036(3) 0.017(2) 0.003(2) 0.015(2) 0.005(2) C21 0.053(4) 0.045(4) 0.042(3) 0.008(3) 0.026(3) 0.011(3) C22 0.068(5) 0.065(5) 0.045(4) 0.003(3) 0.037(3) 0.007(4) C23 0.086(5) 0.058(4) 0.042(4) 0.008(3) 0.043(4) 0.000(4) C24 0.125(7) 0.051(4) 0.052(4) 0.028(3) 0.055(5) 0.025(4) C25 0.090(5) 0.047(4) 0.042(4) 0.016(3) 0.040(4) 0.027(4) C26 0.036(3) 0.023(3) 0.024(3) 0.000(2) 0.009(2) 0.001(2) C27 0.055(4) 0.032(3) 0.023(3) 0.000(2) 0.003(3) 0.000(3) C28 0.076(5) 0.035(3) 0.033(3) 0.002(3) 0.003(3) -0.008(3) C29 0.062(4) 0.027(3) 0.043(4) -0.007(3) 0.007(3) -0.004(3) C30 0.062(4) 0.043(4) 0.026(3) -0.013(3) 0.012(3) -0.007(3) C31 0.053(4) 0.040(3) 0.024(3) -0.005(2) 0.014(3) -0.001(3) C32 0.028(3) 0.033(3) 0.013(2) 0.002(2) 0.006(2) 0.003(2) C33 0.035(3) 0.032(3) 0.017(2) -0.002(2) 0.006(2) 0.000(2) C34 0.037(3) 0.036(3) 0.017(2) 0.003(2) 0.010(2) 0.008(2) C35 0.035(3) 0.049(3) 0.018(3) 0.005(2) 0.009(2) 0.012(3) C36 0.032(3) 0.054(4) 0.032(3) -0.002(3) 0.006(2) -0.005(3) C37 0.039(3) 0.032(3) 0.026(3) -0.002(2) 0.007(2) -0.004(2) C38 0.033(3) 0.021(2) 0.016(2) 0.0005(19) 0.005(2) 0.000(2) C39 0.036(3) 0.037(3) 0.024(3) -0.006(2) 0.011(2) 0.002(2) C40 0.028(3) 0.047(4) 0.037(3) -0.003(3) 0.000(2) 0.001(3) C41 0.041(3) 0.040(3) 0.020(3) 0.000(2) -0.001(2) 0.000(3) C42 0.042(3) 0.037(3) 0.018(3) -0.004(2) 0.008(2) -0.002(2) C43 0.027(3) 0.035(3) 0.021(3) 0.002(2) 0.006(2) 0.000(2) C44 0.041(3) 0.054(4) 0.033(3) 0.011(3) 0.009(3) -0.005(3) Cl2 0.1119(16) 0.0641(12) 0.0315(9) 0.0112(8) -0.0064(9) 0.0131(11) Cl3 0.0985(14) 0.0581(11) 0.0511(10) -0.0173(8) 0.0438(10) -0.0239(10) C45 0.107(7) 0.101(7) 0.046(4) 0.010(4) 0.038(4) 0.044(6) Cl4 0.0760(15) 0.167(3) 0.0677(14) 0.0095(15) 0.0285(12) 0.0422(16) Cl5 0.141(2) 0.0767(16) 0.1030(19) 0.0348(14) 0.0603(17) 0.0360(15) _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 O2 2.081(3) . ? Fe1 O4 2.103(4) . ? Fe1 N3 2.179(4) . ? Fe1 N2 2.181(4) . ? Fe1 N1 2.251(4) . ? Fe1 Cl1 2.3176(15) . ? N1 C1 1.466(6) . ? N1 C3 1.469(6) . ? N1 C5 1.517(6) . ? C1 C2 1.558(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O1 1.214(6) . ? C2 O2 1.262(6) . ? C3 C4 1.547(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O3 1.223(6) . ? C4 O4 1.257(6) . ? C5 C6 1.523(7) . ? C5 C11 1.545(7) . ? C5 C16 1.552(7) . ? C6 N2 1.354(6) . ? C6 C7 1.379(7) . ? C7 C8 1.370(8) . ? C7 H7A 0.9500 . ? C8 C9 1.387(9) . ? C8 H8A 0.9500 . ? C9 C10 1.374(8) . ? C9 H9A 0.9500 . ? C10 N2 1.331(7) . ? C10 H10A 0.9500 . ? C11 N3 1.347(6) . ? C11 C12 1.402(7) . ? C12 C13 1.364(8) . ? C12 H12A 0.9500 . ? C13 C14 1.357(8) . ? C13 H13A 0.9500 . ? C14 C15 1.384(8) . ? C14 H14A 0.9500 . ? C15 N3 1.321(7) . ? C15 H15A 0.9500 . ? C16 C17 1.473(8) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.557(8) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.464(10) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? P1 C26 1.786(5) . ? P1 C38 1.792(5) . ? P1 C32 1.793(5) . ? P1 C20 1.799(5) . ? C20 C21 1.384(8) . ? C20 C25 1.385(8) . ? C21 C22 1.388(8) . ? C21 H21A 0.9500 . ? C22 C23 1.361(9) . ? C22 H22A 0.9500 . ? C23 C24 1.351(10) . ? C23 H23A 0.9500 . ? C24 C25 1.387(9) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 C27 1.389(7) . ? C26 C31 1.393(7) . ? C27 C28 1.371(8) . ? C27 H27A 0.9500 . ? C28 C29 1.380(8) . ? C28 H28A 0.9500 . ? C29 C30 1.373(8) . ? C29 H29A 0.9500 . ? C30 C31 1.379(8) . ? C30 H30A 0.9500 . ? C31 H31A 0.9500 . ? C32 C33 1.385(7) . ? C32 C37 1.393(7) . ? C33 C34 1.386(7) . ? C33 H33A 0.9500 . ? C34 C35 1.371(8) . ? C34 H34A 0.9500 . ? C35 C36 1.379(8) . ? C35 H35A 0.9500 . ? C36 C37 1.370(8) . ? C36 H36A 0.9500 . ? C37 H37A 0.9500 . ? C38 C39 1.386(7) . ? C38 C43 1.397(7) . ? C39 C40 1.384(7) . ? C39 H39A 0.9500 . ? C40 C41 1.390(8) . ? C40 H40A 0.9500 . ? C41 C42 1.354(8) . ? C41 H41A 0.9500 . ? C42 C43 1.392(7) . ? C42 H42A 0.9500 . ? C43 H43A 0.9500 . ? C44 Cl3 1.751(6) . ? C44 Cl2 1.757(6) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 Cl5 1.749(10) . ? C45 Cl4 1.768(8) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? 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 O2 Fe1 O4 86.17(14) . . ? O2 Fe1 N3 154.09(15) . . ? O4 Fe1 N3 91.54(15) . . ? O2 Fe1 N2 88.63(15) . . ? O4 Fe1 N2 153.07(15) . . ? N3 Fe1 N2 81.79(16) . . ? O2 Fe1 N1 79.69(13) . . ? O4 Fe1 N1 78.35(14) . . ? N3 Fe1 N1 74.57(15) . . ? N2 Fe1 N1 74.73(15) . . ? O2 Fe1 Cl1 109.56(10) . . ? O4 Fe1 Cl1 102.22(10) . . ? N3 Fe1 Cl1 96.17(12) . . ? N2 Fe1 Cl1 104.41(12) . . ? N1 Fe1 Cl1 170.74(11) . . ? C1 N1 C3 112.6(4) . . ? C1 N1 C5 115.3(4) . . ? C3 N1 C5 114.0(4) . . ? C1 N1 Fe1 106.1(3) . . ? C3 N1 Fe1 106.4(3) . . ? C5 N1 Fe1 101.1(3) . . ? N1 C1 C2 114.5(4) . . ? N1 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? N1 C1 H1B 108.6 . . ? C2 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? O1 C2 O2 126.5(4) . . ? O1 C2 C1 117.2(4) . . ? O2 C2 C1 116.3(4) . . ? C2 O2 Fe1 118.9(3) . . ? N1 C3 C4 114.1(4) . . ? N1 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? N1 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? O3 C4 O4 126.0(5) . . ? O3 C4 C3 116.2(4) . . ? O4 C4 C3 117.7(4) . . ? C4 O4 Fe1 118.1(3) . . ? N1 C5 C6 106.8(4) . . ? N1 C5 C11 106.1(4) . . ? C6 C5 C11 103.2(4) . . ? N1 C5 C16 114.7(4) . . ? C6 C5 C16 115.4(4) . . ? C11 C5 C16 109.5(4) . . ? N2 C6 C7 121.4(5) . . ? N2 C6 C5 113.8(4) . . ? C7 C6 C5 124.6(5) . . ? C8 C7 C6 119.2(5) . . ? C8 C7 H7A 120.4 . . ? C6 C7 H7A 120.4 . . ? C7 C8 C9 119.6(5) . . ? C7 C8 H8A 120.2 . . ? C9 C8 H8A 120.2 . . ? C10 C9 C8 118.1(6) . . ? C10 C9 H9A 120.9 . . ? C8 C9 H9A 120.9 . . ? N2 C10 C9 122.9(5) . . ? N2 C10 H10A 118.5 . . ? C9 C10 H10A 118.5 . . ? C10 N2 C6 118.7(5) . . ? C10 N2 Fe1 126.3(4) . . ? C6 N2 Fe1 114.9(3) . . ? N3 C11 C12 120.9(5) . . ? N3 C11 C5 115.6(4) . . ? C12 C11 C5 123.3(5) . . ? C13 C12 C11 118.7(5) . . ? C13 C12 H12A 120.7 . . ? C11 C12 H12A 120.7 . . ? C14 C13 C12 120.2(5) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C13 C14 C15 118.6(5) . . ? C13 C14 H14A 120.7 . . ? C15 C14 H14A 120.7 . . ? N3 C15 C14 122.8(5) . . ? N3 C15 H15A 118.6 . . ? C14 C15 H15A 118.6 . . ? C15 N3 C11 118.8(4) . . ? C15 N3 Fe1 127.2(4) . . ? C11 N3 Fe1 113.4(3) . . ? C17 C16 C5 120.8(5) . . ? C17 C16 H16A 107.1 . . ? C5 C16 H16A 107.1 . . ? C17 C16 H16B 107.1 . . ? C5 C16 H16B 107.1 . . ? H16A C16 H16B 106.8 . . ? C16 C17 C18 111.0(5) . . ? C16 C17 H17A 109.4 . . ? C18 C17 H17A 109.4 . . ? C16 C17 H17B 109.4 . . ? C18 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? C19 C18 C17 112.5(6) . . ? C19 C18 H18A 109.1 . . ? C17 C18 H18A 109.1 . . ? C19 C18 H18B 109.1 . . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C26 P1 C38 108.1(2) . . ? C26 P1 C32 110.0(2) . . ? C38 P1 C32 110.8(2) . . ? C26 P1 C20 109.3(2) . . ? C38 P1 C20 110.7(2) . . ? C32 P1 C20 108.0(2) . . ? C21 C20 C25 119.0(5) . . ? C21 C20 P1 121.3(4) . . ? C25 C20 P1 119.6(4) . . ? C20 C21 C22 119.9(6) . . ? C20 C21 H21A 120.1 . . ? C22 C21 H21A 120.1 . . ? C23 C22 C21 120.5(6) . . ? C23 C22 H22A 119.8 . . ? C21 C22 H22A 119.8 . . ? C24 C23 C22 119.7(6) . . ? C24 C23 H23A 120.1 . . ? C22 C23 H23A 120.1 . . ? C23 C24 C25 121.3(6) . . ? C23 C24 H24A 119.4 . . ? C25 C24 H24A 119.4 . . ? C20 C25 C24 119.4(6) . . ? C20 C25 H25A 120.3 . . ? C24 C25 H25A 120.3 . . ? C27 C26 C31 119.1(5) . . ? C27 C26 P1 118.9(4) . . ? C31 C26 P1 121.8(4) . . ? C28 C27 C26 120.2(5) . . ? C28 C27 H27A 119.9 . . ? C26 C27 H27A 119.9 . . ? C27 C28 C29 120.4(6) . . ? C27 C28 H28A 119.8 . . ? C29 C28 H28A 119.8 . . ? C30 C29 C28 120.0(5) . . ? C30 C29 H29A 120.0 . . ? C28 C29 H29A 120.0 . . ? C29 C30 C31 120.1(5) . . ? C29 C30 H30A 120.0 . . ? C31 C30 H30A 120.0 . . ? C30 C31 C26 120.2(5) . . ? C30 C31 H31A 119.9 . . ? C26 C31 H31A 119.9 . . ? C33 C32 C37 119.9(5) . . ? C33 C32 P1 120.6(4) . . ? C37 C32 P1 119.2(4) . . ? C32 C33 C34 120.2(5) . . ? C32 C33 H33A 119.9 . . ? C34 C33 H33A 119.9 . . ? C35 C34 C33 118.9(5) . . ? C35 C34 H34A 120.5 . . ? C33 C34 H34A 120.5 . . ? C34 C35 C36 121.4(5) . . ? C34 C35 H35A 119.3 . . ? C36 C35 H35A 119.3 . . ? C37 C36 C35 120.0(5) . . ? C37 C36 H36A 120.0 . . ? C35 C36 H36A 120.0 . . ? C36 C37 C32 119.6(5) . . ? C36 C37 H37A 120.2 . . ? C32 C37 H37A 120.2 . . ? C39 C38 C43 119.5(4) . . ? C39 C38 P1 120.3(4) . . ? C43 C38 P1 120.1(4) . . ? C40 C39 C38 120.6(5) . . ? C40 C39 H39A 119.7 . . ? C38 C39 H39A 119.7 . . ? C39 C40 C41 119.2(5) . . ? C39 C40 H40A 120.4 . . ? C41 C40 H40A 120.4 . . ? C42 C41 C40 120.7(5) . . ? C42 C41 H41A 119.7 . . ? C40 C41 H41A 119.7 . . ? C41 C42 C43 121.0(5) . . ? C41 C42 H42A 119.5 . . ? C43 C42 H42A 119.5 . . ? C42 C43 C38 119.1(5) . . ? C42 C43 H43A 120.5 . . ? C38 C43 H43A 120.5 . . ? Cl3 C44 Cl2 111.2(3) . . ? Cl3 C44 H44A 109.4 . . ? Cl2 C44 H44A 109.4 . . ? Cl3 C44 H44B 109.4 . . ? Cl2 C44 H44B 109.4 . . ? H44A C44 H44B 108.0 . . ? Cl5 C45 Cl4 112.0(5) . . ? Cl5 C45 H45A 109.2 . . ? Cl4 C45 H45A 109.2 . . ? Cl5 C45 H45B 109.2 . . ? Cl4 C45 H45B 109.2 . . ? H45A C45 H45B 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Fe1 N1 C1 -12.1(3) . . . . ? O4 Fe1 N1 C1 -100.3(3) . . . . ? N3 Fe1 N1 C1 164.8(3) . . . . ? N2 Fe1 N1 C1 79.3(3) . . . . ? Cl1 Fe1 N1 C1 165.2(6) . . . . ? O2 Fe1 N1 C3 107.9(3) . . . . ? O4 Fe1 N1 C3 19.8(3) . . . . ? N3 Fe1 N1 C3 -75.1(3) . . . . ? N2 Fe1 N1 C3 -160.6(3) . . . . ? Cl1 Fe1 N1 C3 -74.7(8) . . . . ? O2 Fe1 N1 C5 -132.8(3) . . . . ? O4 Fe1 N1 C5 139.1(3) . . . . ? N3 Fe1 N1 C5 44.2(3) . . . . ? N2 Fe1 N1 C5 -41.3(3) . . . . ? Cl1 Fe1 N1 C5 44.6(9) . . . . ? C3 N1 C1 C2 -94.8(5) . . . . ? C5 N1 C1 C2 132.2(4) . . . . ? Fe1 N1 C1 C2 21.2(5) . . . . ? N1 C1 C2 O1 156.7(4) . . . . ? N1 C1 C2 O2 -23.6(6) . . . . ? O1 C2 O2 Fe1 -168.3(4) . . . . ? C1 C2 O2 Fe1 12.1(6) . . . . ? O4 Fe1 O2 C2 79.0(4) . . . . ? N3 Fe1 O2 C2 -6.7(6) . . . . ? N2 Fe1 O2 C2 -74.6(4) . . . . ? N1 Fe1 O2 C2 0.1(3) . . . . ? Cl1 Fe1 O2 C2 -179.4(3) . . . . ? C1 N1 C3 C4 93.4(5) . . . . ? C5 N1 C3 C4 -132.9(4) . . . . ? Fe1 N1 C3 C4 -22.4(5) . . . . ? N1 C3 C4 O3 -169.8(4) . . . . ? N1 C3 C4 O4 12.0(6) . . . . ? O3 C4 O4 Fe1 -170.8(4) . . . . ? C3 C4 O4 Fe1 7.2(6) . . . . ? O2 Fe1 O4 C4 -95.9(4) . . . . ? N3 Fe1 O4 C4 58.3(4) . . . . ? N2 Fe1 O4 C4 -16.5(5) . . . . ? N1 Fe1 O4 C4 -15.6(3) . . . . ? Cl1 Fe1 O4 C4 154.9(3) . . . . ? C1 N1 C5 C6 -58.3(5) . . . . ? C3 N1 C5 C6 169.3(4) . . . . ? Fe1 N1 C5 C6 55.6(4) . . . . ? C1 N1 C5 C11 -168.0(4) . . . . ? C3 N1 C5 C11 59.6(5) . . . . ? Fe1 N1 C5 C11 -54.1(4) . . . . ? C1 N1 C5 C16 70.9(6) . . . . ? C3 N1 C5 C16 -61.5(6) . . . . ? Fe1 N1 C5 C16 -175.2(4) . . . . ? N1 C5 C6 N2 -41.5(5) . . . . ? C11 C5 C6 N2 70.2(5) . . . . ? C16 C5 C6 N2 -170.3(4) . . . . ? N1 C5 C6 C7 144.2(5) . . . . ? C11 C5 C6 C7 -104.2(5) . . . . ? C16 C5 C6 C7 15.3(7) . . . . ? N2 C6 C7 C8 0.1(8) . . . . ? C5 C6 C7 C8 174.0(5) . . . . ? C6 C7 C8 C9 -1.2(9) . . . . ? C7 C8 C9 C10 1.6(9) . . . . ? C8 C9 C10 N2 -0.9(9) . . . . ? C9 C10 N2 C6 -0.2(8) . . . . ? C9 C10 N2 Fe1 -177.0(4) . . . . ? C7 C6 N2 C10 0.6(8) . . . . ? C5 C6 N2 C10 -173.9(5) . . . . ? C7 C6 N2 Fe1 177.8(4) . . . . ? C5 C6 N2 Fe1 3.2(5) . . . . ? O2 Fe1 N2 C10 -80.8(4) . . . . ? O4 Fe1 N2 C10 -159.6(4) . . . . ? N3 Fe1 N2 C10 123.4(5) . . . . ? N1 Fe1 N2 C10 -160.5(5) . . . . ? Cl1 Fe1 N2 C10 29.1(5) . . . . ? O2 Fe1 N2 C6 102.3(4) . . . . ? O4 Fe1 N2 C6 23.5(5) . . . . ? N3 Fe1 N2 C6 -53.6(4) . . . . ? N1 Fe1 N2 C6 22.6(3) . . . . ? Cl1 Fe1 N2 C6 -147.9(3) . . . . ? N1 C5 C11 N3 35.5(6) . . . . ? C6 C5 C11 N3 -76.7(5) . . . . ? C16 C5 C11 N3 159.8(4) . . . . ? N1 C5 C11 C12 -149.9(5) . . . . ? C6 C5 C11 C12 97.9(5) . . . . ? C16 C5 C11 C12 -25.5(7) . . . . ? N3 C11 C12 C13 0.4(8) . . . . ? C5 C11 C12 C13 -173.9(5) . . . . ? C11 C12 C13 C14 -2.1(9) . . . . ? C12 C13 C14 C15 1.7(9) . . . . ? C13 C14 C15 N3 0.5(10) . . . . ? C14 C15 N3 C11 -2.2(9) . . . . ? C14 C15 N3 Fe1 168.4(5) . . . . ? C12 C11 N3 C15 1.7(8) . . . . ? C5 C11 N3 C15 176.5(5) . . . . ? C12 C11 N3 Fe1 -170.2(4) . . . . ? C5 C11 N3 Fe1 4.6(5) . . . . ? O2 Fe1 N3 C15 167.6(4) . . . . ? O4 Fe1 N3 C15 83.2(5) . . . . ? N2 Fe1 N3 C15 -123.0(5) . . . . ? N1 Fe1 N3 C15 160.7(5) . . . . ? Cl1 Fe1 N3 C15 -19.2(5) . . . . ? O2 Fe1 N3 C11 -21.3(6) . . . . ? O4 Fe1 N3 C11 -105.7(4) . . . . ? N2 Fe1 N3 C11 48.1(4) . . . . ? N1 Fe1 N3 C11 -28.2(3) . . . . ? Cl1 Fe1 N3 C11 151.8(3) . . . . ? N1 C5 C16 C17 -52.7(7) . . . . ? C6 C5 C16 C17 72.1(7) . . . . ? C11 C5 C16 C17 -171.9(5) . . . . ? C5 C16 C17 C18 -175.2(5) . . . . ? C16 C17 C18 C19 -178.3(6) . . . . ? C26 P1 C20 C21 -38.0(6) . . . . ? C38 P1 C20 C21 81.0(5) . . . . ? C32 P1 C20 C21 -157.6(5) . . . . ? C26 P1 C20 C25 141.3(5) . . . . ? C38 P1 C20 C25 -99.8(5) . . . . ? C32 P1 C20 C25 21.7(6) . . . . ? C25 C20 C21 C22 1.1(9) . . . . ? P1 C20 C21 C22 -179.7(5) . . . . ? C20 C21 C22 C23 2.1(10) . . . . ? C21 C22 C23 C24 -5.0(12) . . . . ? C22 C23 C24 C25 4.7(13) . . . . ? C21 C20 C25 C24 -1.4(10) . . . . ? P1 C20 C25 C24 179.3(6) . . . . ? C23 C24 C25 C20 -1.5(13) . . . . ? C38 P1 C26 C27 32.1(5) . . . . ? C32 P1 C26 C27 -89.0(5) . . . . ? C20 P1 C26 C27 152.6(4) . . . . ? C38 P1 C26 C31 -152.4(5) . . . . ? C32 P1 C26 C31 86.6(5) . . . . ? C20 P1 C26 C31 -31.8(5) . . . . ? C31 C26 C27 C28 0.6(9) . . . . ? P1 C26 C27 C28 176.3(5) . . . . ? C26 C27 C28 C29 0.2(10) . . . . ? C27 C28 C29 C30 -0.5(11) . . . . ? C28 C29 C30 C31 0.0(10) . . . . ? C29 C30 C31 C26 0.7(9) . . . . ? C27 C26 C31 C30 -1.0(9) . . . . ? P1 C26 C31 C30 -176.5(5) . . . . ? C26 P1 C32 C33 160.6(4) . . . . ? C38 P1 C32 C33 41.2(5) . . . . ? C20 P1 C32 C33 -80.2(4) . . . . ? C26 P1 C32 C37 -25.9(5) . . . . ? C38 P1 C32 C37 -145.3(4) . . . . ? C20 P1 C32 C37 93.3(4) . . . . ? C37 C32 C33 C34 -0.2(7) . . . . ? P1 C32 C33 C34 173.2(4) . . . . ? C32 C33 C34 C35 0.2(7) . . . . ? C33 C34 C35 C36 -0.2(8) . . . . ? C34 C35 C36 C37 0.3(8) . . . . ? C35 C36 C37 C32 -0.4(8) . . . . ? C33 C32 C37 C36 0.3(7) . . . . ? P1 C32 C37 C36 -173.2(4) . . . . ? C26 P1 C38 C39 82.7(4) . . . . ? C32 P1 C38 C39 -156.8(4) . . . . ? C20 P1 C38 C39 -37.0(5) . . . . ? C26 P1 C38 C43 -93.8(4) . . . . ? C32 P1 C38 C43 26.8(5) . . . . ? C20 P1 C38 C43 146.6(4) . . . . ? C43 C38 C39 C40 0.8(8) . . . . ? P1 C38 C39 C40 -175.7(4) . . . . ? C38 C39 C40 C41 -0.6(8) . . . . ? C39 C40 C41 C42 0.0(9) . . . . ? C40 C41 C42 C43 0.3(9) . . . . ? C41 C42 C43 C38 -0.1(8) . . . . ? C39 C38 C43 C42 -0.5(7) . . . . ? P1 C38 C43 C42 176.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.189 _refine_diff_density_min -0.726 _refine_diff_density_rms 0.107 # Attachment '4(a).cif' data_08126s _database_code_depnum_ccdc_archive 'CCDC 857971' #TrackingRef '4(a).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 08126 _chemical_melting_point ? _chemical_formula_moiety 'C30 H26 Fe2 N6 O9' _chemical_formula_sum 'C30 H26 Fe2 N6 O9' _chemical_formula_weight 726.27 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.810(3) _cell_length_b 8.8413(12) _cell_length_c 23.661(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.478(2) _cell_angle_gamma 90.00 _cell_volume 3709.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2637 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 24.58 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.836 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8183 _exptl_absorpt_correction_T_max 0.9594 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10307 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.06 _reflns_number_total 3283 _reflns_number_gt 2489 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _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. The sample contains solvent channels that appear to hold deuterated acetonitrile, however attempts to model the solvent were unsuccessful. Thus the electron density was modeled as solvent accessible void space using the function SQUEEZE in the program PLATON. A void space of 1069.5 angstroms^3^ (28.8% of the volume), containing 241 electrons (roughly 11 acetonitrile solvent molecules) per cell was found. ; _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^)+(0.0438P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3283 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0799 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.212078(18) 0.69680(4) 0.423191(15) 0.01905(12) Uani 1 1 d . . . O1 O 0.23126(10) 0.87088(18) 0.37653(8) 0.0282(4) Uani 1 1 d . . . O2 O 0.22470(12) 0.9616(2) 0.28701(9) 0.0473(5) Uani 1 1 d . . . O3 O 0.10249(9) 0.74003(19) 0.39700(8) 0.0279(4) Uani 1 1 d . . . O4 O -0.00861(10) 0.7164(2) 0.32441(9) 0.0384(5) Uani 1 1 d . . . O5 O 0.2500 0.7500 0.5000 0.0270(6) Uani 1 2 d S . . N1 N 0.17715(11) 0.5961(2) 0.33168(8) 0.0221(5) Uani 1 1 d . . . N2 N 0.31373(11) 0.5962(2) 0.41745(9) 0.0217(5) Uani 1 1 d . . . N3 N 0.18748(11) 0.4563(2) 0.43355(9) 0.0223(5) Uani 1 1 d . . . C1 C 0.21963(15) 0.8572(3) 0.31955(12) 0.0296(6) Uani 1 1 d . . . C2 C 0.20125(15) 0.7000(3) 0.29260(11) 0.0300(6) Uani 1 1 d . . . H2A H 0.1606 0.7077 0.2533 0.036 Uiso 1 1 calc R . . H2B H 0.2463 0.6577 0.2856 0.036 Uiso 1 1 calc R . . C3 C 0.05893(14) 0.6881(3) 0.34605(11) 0.0262(6) Uani 1 1 d . . . C4 C 0.09370(14) 0.5804(3) 0.31247(11) 0.0272(6) Uani 1 1 d . . . H4A H 0.0808 0.4751 0.3195 0.033 Uiso 1 1 calc R . . H4B H 0.0720 0.6009 0.2689 0.033 Uiso 1 1 calc R . . C5 C 0.21998(14) 0.4501(3) 0.34395(11) 0.0239(6) Uani 1 1 d . . . H5A H 0.2117 0.3896 0.3066 0.029 Uiso 1 1 calc R . . C6 C 0.30261(14) 0.4907(3) 0.37419(11) 0.0245(6) Uani 1 1 d . . . C7 C 0.36182(15) 0.4237(3) 0.36170(12) 0.0341(7) Uani 1 1 d . . . H7A H 0.3530 0.3473 0.3319 0.041 Uiso 1 1 calc R . . C8 C 0.43488(16) 0.4704(3) 0.39368(13) 0.0410(7) Uani 1 1 d . . . H8A H 0.4768 0.4272 0.3857 0.049 Uiso 1 1 calc R . . C9 C 0.44560(15) 0.5801(3) 0.43709(13) 0.0363(7) Uani 1 1 d . . . H9A H 0.4950 0.6140 0.4591 0.044 Uiso 1 1 calc R . . C10 C 0.38412(14) 0.6405(3) 0.44849(12) 0.0295(6) Uani 1 1 d . . . H10A H 0.3918 0.7150 0.4789 0.035 Uiso 1 1 calc R . . C11 C 0.19381(13) 0.3662(3) 0.38955(11) 0.0224(5) Uani 1 1 d . . . C12 C 0.17928(14) 0.2124(3) 0.38774(12) 0.0326(6) Uani 1 1 d . . . H12A H 0.1847 0.1511 0.3565 0.039 Uiso 1 1 calc R . . C13 C 0.15672(14) 0.1508(3) 0.43257(13) 0.0353(7) Uani 1 1 d . . . H13A H 0.1466 0.0456 0.4327 0.042 Uiso 1 1 calc R . . C14 C 0.14894(14) 0.2425(3) 0.47708(13) 0.0332(7) Uani 1 1 d . . . H14A H 0.1324 0.2016 0.5077 0.040 Uiso 1 1 calc R . . C15 C 0.16547(13) 0.3942(3) 0.47677(12) 0.0272(6) Uani 1 1 d . . . H15A H 0.1612 0.4568 0.5081 0.033 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 0.02524(19) 0.01636(18) 0.01372(19) -0.00213(15) 0.00406(14) 0.00142(15) O1 0.0424(11) 0.0188(9) 0.0239(10) 0.0001(8) 0.0119(9) -0.0001(8) O2 0.0735(15) 0.0334(11) 0.0337(12) 0.0105(10) 0.0163(11) -0.0064(10) O3 0.0286(10) 0.0283(10) 0.0228(10) -0.0067(8) 0.0035(8) 0.0035(7) O4 0.0261(10) 0.0482(12) 0.0342(11) -0.0058(9) 0.0012(9) 0.0053(9) O5 0.0313(14) 0.0292(13) 0.0172(13) -0.0055(11) 0.0037(11) -0.0003(11) N1 0.0311(11) 0.0184(11) 0.0143(11) 0.0005(8) 0.0044(9) 0.0055(8) N2 0.0287(11) 0.0206(11) 0.0162(11) 0.0011(9) 0.0080(9) 0.0019(9) N3 0.0248(11) 0.0227(11) 0.0163(11) -0.0012(9) 0.0026(9) 0.0010(8) C1 0.0370(15) 0.0276(14) 0.0252(15) 0.0052(12) 0.0118(12) 0.0041(12) C2 0.0450(16) 0.0287(14) 0.0157(13) 0.0045(12) 0.0094(12) 0.0080(12) C3 0.0290(14) 0.0241(13) 0.0218(14) 0.0025(12) 0.0034(11) 0.0004(11) C4 0.0310(14) 0.0243(13) 0.0182(13) -0.0035(11) -0.0023(11) 0.0036(11) C5 0.0345(14) 0.0179(13) 0.0158(13) -0.0043(10) 0.0035(11) 0.0055(10) C6 0.0369(15) 0.0210(13) 0.0163(13) 0.0025(11) 0.0098(11) 0.0067(11) C7 0.0407(17) 0.0385(16) 0.0262(15) -0.0021(13) 0.0151(13) 0.0096(13) C8 0.0369(17) 0.0545(19) 0.0369(17) 0.0065(15) 0.0193(14) 0.0155(14) C9 0.0293(15) 0.0434(17) 0.0358(17) 0.0024(14) 0.0103(13) 0.0003(12) C10 0.0271(14) 0.0305(14) 0.0299(15) 0.0000(12) 0.0080(12) 0.0013(11) C11 0.0230(13) 0.0198(12) 0.0188(14) -0.0018(11) -0.0005(11) 0.0029(10) C12 0.0348(15) 0.0198(14) 0.0362(17) -0.0062(12) 0.0026(13) 0.0013(11) C13 0.0317(15) 0.0191(13) 0.0483(19) 0.0042(13) 0.0044(14) -0.0043(11) C14 0.0291(15) 0.0297(14) 0.0389(17) 0.0102(13) 0.0090(13) -0.0014(11) C15 0.0251(13) 0.0297(15) 0.0248(14) 0.0024(12) 0.0056(11) 0.0005(11) _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 O5 1.7800(4) . ? Fe1 O3 1.9819(17) . ? Fe1 O1 1.9959(17) . ? Fe1 N2 2.1539(19) . ? Fe1 N3 2.207(2) . ? Fe1 N1 2.2282(19) . ? O1 C1 1.298(3) . ? O2 C1 1.226(3) . ? O3 C3 1.295(3) . ? O4 C3 1.227(3) . ? O5 Fe1 1.7798(4) 7_566 ? N1 C2 1.478(3) . ? N1 C4 1.488(3) . ? N1 C5 1.497(3) . ? N2 C10 1.341(3) . ? N2 C6 1.349(3) . ? N3 C15 1.342(3) . ? N3 C11 1.347(3) . ? C1 C2 1.520(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.520(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C11 1.520(3) . ? C5 C6 1.521(4) . ? C5 H5A 1.0000 . ? C6 C7 1.377(3) . ? C7 C8 1.392(4) . ? C7 H7A 0.9500 . ? C8 C9 1.378(4) . ? C8 H8A 0.9500 . ? C9 C10 1.380(4) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 C12 1.384(3) . ? C12 C13 1.379(4) . ? C12 H12A 0.9500 . ? C13 C14 1.375(4) . ? C13 H13A 0.9500 . ? C14 C15 1.378(4) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? 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 O5 Fe1 O3 106.81(5) . . ? O5 Fe1 O1 106.03(5) . . ? O3 Fe1 O1 92.26(7) . . ? O5 Fe1 N2 96.40(5) . . ? O3 Fe1 N2 155.88(7) . . ? O1 Fe1 N2 87.46(7) . . ? O5 Fe1 N3 99.71(5) . . ? O3 Fe1 N3 89.18(7) . . ? O1 Fe1 N3 152.58(7) . . ? N2 Fe1 N3 80.36(7) . . ? O5 Fe1 N1 170.31(5) . . ? O3 Fe1 N1 80.46(7) . . ? O1 Fe1 N1 79.62(7) . . ? N2 Fe1 N1 75.76(7) . . ? N3 Fe1 N1 73.62(7) . . ? C1 O1 Fe1 120.28(16) . . ? C3 O3 Fe1 119.46(15) . . ? Fe1 O5 Fe1 179.996(1) 7_566 . ? C2 N1 C4 112.28(19) . . ? C2 N1 C5 113.56(19) . . ? C4 N1 C5 115.08(18) . . ? C2 N1 Fe1 107.86(14) . . ? C4 N1 Fe1 105.86(14) . . ? C5 N1 Fe1 100.99(13) . . ? C10 N2 C6 119.5(2) . . ? C10 N2 Fe1 125.45(17) . . ? C6 N2 Fe1 114.66(16) . . ? C15 N3 C11 118.4(2) . . ? C15 N3 Fe1 127.46(16) . . ? C11 N3 Fe1 114.09(16) . . ? O2 C1 O1 124.1(2) . . ? O2 C1 C2 118.7(2) . . ? O1 C1 C2 117.2(2) . . ? N1 C2 C1 112.4(2) . . ? N1 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? O4 C3 O3 124.2(2) . . ? O4 C3 C4 118.4(2) . . ? O3 C3 C4 117.4(2) . . ? N1 C4 C3 112.09(19) . . ? N1 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? N1 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N1 C5 C11 106.12(19) . . ? N1 C5 C6 106.72(18) . . ? C11 C5 C6 107.64(19) . . ? N1 C5 H5A 112.0 . . ? C11 C5 H5A 112.0 . . ? C6 C5 H5A 112.0 . . ? N2 C6 C7 121.9(2) . . ? N2 C6 C5 113.3(2) . . ? C7 C6 C5 124.8(2) . . ? C6 C7 C8 118.6(3) . . ? C6 C7 H7A 120.7 . . ? C8 C7 H7A 120.7 . . ? C9 C8 C7 119.1(3) . . ? C9 C8 H8A 120.4 . . ? C7 C8 H8A 120.4 . . ? C8 C9 C10 119.6(3) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? N2 C10 C9 121.2(3) . . ? N2 C10 H10A 119.4 . . ? C9 C10 H10A 119.4 . . ? N3 C11 C12 122.5(2) . . ? N3 C11 C5 113.1(2) . . ? C12 C11 C5 124.4(2) . . ? C13 C12 C11 118.2(3) . . ? C13 C12 H12A 120.9 . . ? C11 C12 H12A 120.9 . . ? C14 C13 C12 119.7(2) . . ? C14 C13 H13A 120.2 . . ? C12 C13 H13A 120.2 . . ? C13 C14 C15 119.2(3) . . ? C13 C14 H14A 120.4 . . ? C15 C14 H14A 120.4 . . ? N3 C15 C14 122.0(2) . . ? N3 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Fe1 O1 C1 170.06(17) . . . . ? O3 Fe1 O1 C1 -81.73(18) . . . . ? N2 Fe1 O1 C1 74.13(18) . . . . ? N3 Fe1 O1 C1 10.9(3) . . . . ? N1 Fe1 O1 C1 -1.85(18) . . . . ? O5 Fe1 O3 C3 -168.16(16) . . . . ? O1 Fe1 O3 C3 84.34(18) . . . . ? N2 Fe1 O3 C3 -4.5(3) . . . . ? N3 Fe1 O3 C3 -68.26(18) . . . . ? N1 Fe1 O3 C3 5.26(17) . . . . ? O3 Fe1 O5 Fe1 -156(4) . . . 7_566 ? O1 Fe1 O5 Fe1 -58(4) . . . 7_566 ? N2 Fe1 O5 Fe1 31(4) . . . 7_566 ? N3 Fe1 O5 Fe1 112(4) . . . 7_566 ? N1 Fe1 O5 Fe1 66(4) . . . 7_566 ? O5 Fe1 N1 C2 -115.9(3) . . . . ? O3 Fe1 N1 C2 104.78(15) . . . . ? O1 Fe1 N1 C2 10.68(15) . . . . ? N2 Fe1 N1 C2 -79.31(15) . . . . ? N3 Fe1 N1 C2 -163.26(16) . . . . ? O5 Fe1 N1 C4 123.7(3) . . . . ? O3 Fe1 N1 C4 -15.59(14) . . . . ? O1 Fe1 N1 C4 -109.69(15) . . . . ? N2 Fe1 N1 C4 160.32(15) . . . . ? N3 Fe1 N1 C4 76.37(14) . . . . ? O5 Fe1 N1 C5 3.5(4) . . . . ? O3 Fe1 N1 C5 -135.86(15) . . . . ? O1 Fe1 N1 C5 130.05(15) . . . . ? N2 Fe1 N1 C5 40.05(14) . . . . ? N3 Fe1 N1 C5 -43.89(14) . . . . ? O5 Fe1 N2 C10 -31.9(2) . . . . ? O3 Fe1 N2 C10 163.84(19) . . . . ? O1 Fe1 N2 C10 74.0(2) . . . . ? N3 Fe1 N2 C10 -130.7(2) . . . . ? N1 Fe1 N2 C10 153.9(2) . . . . ? O5 Fe1 N2 C6 155.08(15) . . . . ? O3 Fe1 N2 C6 -9.2(3) . . . . ? O1 Fe1 N2 C6 -99.06(17) . . . . ? N3 Fe1 N2 C6 56.27(16) . . . . ? N1 Fe1 N2 C6 -19.13(16) . . . . ? O5 Fe1 N3 C15 33.6(2) . . . . ? O3 Fe1 N3 C15 -73.4(2) . . . . ? O1 Fe1 N3 C15 -166.69(18) . . . . ? N2 Fe1 N3 C15 128.5(2) . . . . ? N1 Fe1 N3 C15 -153.7(2) . . . . ? O5 Fe1 N3 C11 -148.56(15) . . . . ? O3 Fe1 N3 C11 104.52(16) . . . . ? O1 Fe1 N3 C11 11.2(3) . . . . ? N2 Fe1 N3 C11 -53.64(16) . . . . ? N1 Fe1 N3 C11 24.22(15) . . . . ? Fe1 O1 C1 O2 174.4(2) . . . . ? Fe1 O1 C1 C2 -7.8(3) . . . . ? C4 N1 C2 C1 99.3(2) . . . . ? C5 N1 C2 C1 -128.0(2) . . . . ? Fe1 N1 C2 C1 -17.0(2) . . . . ? O2 C1 C2 N1 -164.7(2) . . . . ? O1 C1 C2 N1 17.3(3) . . . . ? Fe1 O3 C3 O4 -175.38(19) . . . . ? Fe1 O3 C3 C4 7.1(3) . . . . ? C2 N1 C4 C3 -94.7(2) . . . . ? C5 N1 C4 C3 133.3(2) . . . . ? Fe1 N1 C4 C3 22.7(2) . . . . ? O4 C3 C4 N1 160.8(2) . . . . ? O3 C3 C4 N1 -21.5(3) . . . . ? C2 N1 C5 C11 174.09(19) . . . . ? C4 N1 C5 C11 -54.6(2) . . . . ? Fe1 N1 C5 C11 58.90(18) . . . . ? C2 N1 C5 C6 59.5(2) . . . . ? C4 N1 C5 C6 -169.16(19) . . . . ? Fe1 N1 C5 C6 -55.69(19) . . . . ? C10 N2 C6 C7 1.6(4) . . . . ? Fe1 N2 C6 C7 175.10(19) . . . . ? C10 N2 C6 C5 178.9(2) . . . . ? Fe1 N2 C6 C5 -7.6(2) . . . . ? N1 C5 C6 N2 44.7(3) . . . . ? C11 C5 C6 N2 -68.9(2) . . . . ? N1 C5 C6 C7 -138.1(2) . . . . ? C11 C5 C6 C7 108.3(3) . . . . ? N2 C6 C7 C8 -2.0(4) . . . . ? C5 C6 C7 C8 -178.9(2) . . . . ? C6 C7 C8 C9 0.8(4) . . . . ? C7 C8 C9 C10 0.6(4) . . . . ? C6 N2 C10 C9 -0.1(4) . . . . ? Fe1 N2 C10 C9 -172.82(19) . . . . ? C8 C9 C10 N2 -1.0(4) . . . . ? C15 N3 C11 C12 -0.7(3) . . . . ? Fe1 N3 C11 C12 -178.81(18) . . . . ? C15 N3 C11 C5 -179.4(2) . . . . ? Fe1 N3 C11 C5 2.6(2) . . . . ? N1 C5 C11 N3 -42.7(2) . . . . ? C6 C5 C11 N3 71.2(2) . . . . ? N1 C5 C11 C12 138.7(2) . . . . ? C6 C5 C11 C12 -107.4(3) . . . . ? N3 C11 C12 C13 0.7(4) . . . . ? C5 C11 C12 C13 179.2(2) . . . . ? C11 C12 C13 C14 0.4(4) . . . . ? C12 C13 C14 C15 -1.4(4) . . . . ? C11 N3 C15 C14 -0.4(3) . . . . ? Fe1 N3 C15 C14 177.43(18) . . . . ? C13 C14 C15 N3 1.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.399 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.059 # Attachment '4(b).cif' data_11031_2m _database_code_depnum_ccdc_archive 'CCDC 857972' #TrackingRef '4(b).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H42 Fe2 N6 O9, 4(C H4 O)' _chemical_formula_sum 'C42 H58 Fe2 N6 O13' _chemical_formula_weight 966.64 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.8834(18) _cell_length_b 8.8381(5) _cell_length_c 24.4677(12) _cell_angle_alpha 90.00 _cell_angle_beta 120.136(3) _cell_angle_gamma 90.00 _cell_volume 4653.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2574 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 20.41 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 0.691 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8462 _exptl_absorpt_correction_T_max 0.9341 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19624 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4400 _reflns_number_gt 3164 _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^)+(0.0668P)^2^+8.8012P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4400 _refine_ls_number_parameters 316 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1529 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.46896(2) 0.55837(6) 0.92048(2) 0.02544(18) Uani 1 1 d . . . O1 O 0.5000 0.5000 1.0000 0.0354(9) Uani 1 2 d S . . O2 O 0.53712(12) 0.5073(3) 0.90383(11) 0.0318(6) Uani 1 1 d . . . O3 O 0.57583(14) 0.5454(4) 0.84056(14) 0.0553(9) Uani 1 1 d . . . O4 O 0.41647(13) 0.3851(3) 0.86985(13) 0.0379(7) Uani 1 1 d . . . O5 O 0.34709(15) 0.2975(4) 0.77463(15) 0.0560(9) Uani 1 1 d . . . N1 N 0.49860(13) 0.7958(3) 0.93123(13) 0.0254(7) Uani 1 1 d . . . N2 N 0.38661(14) 0.6702(4) 0.90726(14) 0.0289(7) Uani 1 1 d . . . N3 N 0.42778(13) 0.6552(3) 0.82357(13) 0.0269(7) Uani 1 1 d . A . C1 C 0.54937(17) 0.8533(5) 0.98068(17) 0.0313(9) Uani 1 1 d . . . H1A H 0.5763 0.7878 1.0141 0.038 Uiso 1 1 calc R . . C2 C 0.56401(19) 1.0056(5) 0.98471(19) 0.0372(9) Uani 1 1 d . . . H2A H 0.6009 1.0440 1.0197 0.045 Uiso 1 1 calc R . . C3 C 0.5240(2) 1.0996(5) 0.93702(19) 0.0381(10) Uani 1 1 d . . . H3A H 0.5326 1.2049 0.9392 0.046 Uiso 1 1 calc R . . C4 C 0.47086(19) 1.0413(4) 0.88547(18) 0.0334(9) Uani 1 1 d . . . H4A H 0.4427 1.1058 0.8524 0.040 Uiso 1 1 calc R . . C5 C 0.45987(17) 0.8874(4) 0.88336(16) 0.0275(8) Uani 1 1 d . A . C6 C 0.40331(17) 0.8063(4) 0.83072(16) 0.0272(8) Uani 1 1 d D . . C7 C 0.36199(17) 0.7723(4) 0.86008(16) 0.0274(8) Uani 1 1 d . A . C8 C 0.30658(17) 0.8435(5) 0.84300(18) 0.0356(9) Uani 1 1 d . . . H8A H 0.2888 0.9122 0.8085 0.043 Uiso 1 1 calc R A . C9 C 0.27743(18) 0.8128(5) 0.87726(19) 0.0401(10) Uani 1 1 d . A . H9A H 0.2391 0.8607 0.8663 0.048 Uiso 1 1 calc R . . C10 C 0.30379(19) 0.7127(5) 0.9273(2) 0.0413(10) Uani 1 1 d . . . H10A H 0.2848 0.6931 0.9520 0.050 Uiso 1 1 calc R A . C11 C 0.35880(18) 0.6414(5) 0.94077(19) 0.0342(9) Uani 1 1 d . A . H11A H 0.3771 0.5706 0.9745 0.041 Uiso 1 1 calc R . . C12 C 0.48009(17) 0.6623(5) 0.81111(17) 0.0315(9) Uani 1 1 d . . . H12A H 0.4944 0.7685 0.8157 0.038 Uiso 1 1 calc R A . H12B H 0.4648 0.6318 0.7668 0.038 Uiso 1 1 calc R . . C13 C 0.53557(18) 0.5626(5) 0.85447(17) 0.0326(9) Uani 1 1 d . A . C14 C 0.37818(18) 0.5504(4) 0.77940(18) 0.0359(9) Uani 1 1 d . . . H14A H 0.3825 0.5342 0.7418 0.043 Uiso 1 1 calc R A . H14B H 0.3371 0.5975 0.7651 0.043 Uiso 1 1 calc R . . C15 C 0.38077(18) 0.3993(5) 0.8095(2) 0.0375(10) Uani 1 1 d . A . O7 O 0.68850(17) 0.4367(5) 0.93800(19) 0.0763(12) Uani 1 1 d . . . H7O H 0.6536 0.4531 0.9060 0.092 Uiso 1 1 calc R . . C21 C 0.7128(4) 0.5710(9) 0.9701(4) 0.111(3) Uani 1 1 d . . . H21A H 0.7009 0.6541 0.9397 0.166 Uiso 1 1 calc R . . H21B H 0.7582 0.5636 0.9947 0.166 Uiso 1 1 calc R . . H21C H 0.6966 0.5902 0.9985 0.166 Uiso 1 1 calc R . . C16 C 0.3683(2) 0.9005(6) 0.7700(2) 0.0270(11) Uani 0.895(3) 1 d PD A 1 H16A H 0.3280 0.8497 0.7424 0.032 Uiso 0.895(3) 1 calc PR A 1 H16B H 0.3587 0.9999 0.7818 0.032 Uiso 0.895(3) 1 calc PR A 1 C17 C 0.3987(2) 0.9306(5) 0.73016(19) 0.0330(10) Uani 0.895(3) 1 d PD A 1 H17A H 0.4401 0.9768 0.7570 0.040 Uiso 0.895(3) 1 calc PR A 1 H17B H 0.4046 0.8335 0.7137 0.040 Uiso 0.895(3) 1 calc PR A 1 C18 C 0.3589(2) 1.0358(6) 0.6751(2) 0.0459(13) Uani 0.895(3) 1 d PD A 1 H18A H 0.3167 0.9929 0.6495 0.055 Uiso 0.895(3) 1 calc PR A 1 H18B H 0.3553 1.1355 0.6914 0.055 Uiso 0.895(3) 1 calc PR A 1 C19 C 0.3880(3) 1.0548(8) 0.6348(3) 0.0648(17) Uani 0.895(3) 1 d PD A 1 H19A H 0.3601 1.1137 0.5971 0.097 Uiso 0.895(3) 1 calc PR A 1 H19B H 0.3951 0.9551 0.6221 0.097 Uiso 0.895(3) 1 calc PR A 1 H19C H 0.4277 1.1080 0.6589 0.097 Uiso 0.895(3) 1 calc PR A 1 O6 O 0.76516(16) 0.6830(4) 0.80449(18) 0.0578(10) Uani 0.895(3) 1 d PD A 1 H6OA H 0.7895 0.7187 0.7934 0.069 Uiso 0.895(3) 1 calc PR A 1 C20 C 0.7841(3) 0.7277(9) 0.8656(3) 0.080(2) Uani 0.895(3) 1 d PD A 1 H20A H 0.7892 0.8379 0.8689 0.119 Uiso 0.895(3) 1 calc PR A 1 H20B H 0.8238 0.6792 0.8947 0.119 Uiso 0.895(3) 1 calc PR A 1 H20C H 0.7528 0.6978 0.8766 0.119 Uiso 0.895(3) 1 calc PR A 1 C16' C 0.355(2) 0.864(4) 0.7650(13) 0.0270(11) Uani 0.105(3) 1 d PD A 2 H16E H 0.3363 0.9546 0.7734 0.032 Uiso 0.105(3) 1 calc PR A 2 H16F H 0.3790 0.9028 0.7461 0.032 Uiso 0.105(3) 1 calc PR A 2 C17' C 0.2994(13) 0.782(3) 0.7110(12) 0.0330(10) Uani 0.105(3) 1 d PD A 2 H17E H 0.3151 0.7035 0.6938 0.040 Uiso 0.105(3) 1 calc PR A 2 H17F H 0.2753 0.7312 0.7277 0.040 Uiso 0.105(3) 1 calc PR A 2 C18' C 0.2568(15) 0.889(4) 0.6579(13) 0.0459(13) Uani 0.105(3) 1 d PD A 2 H18E H 0.2377 0.9626 0.6737 0.055 Uiso 0.105(3) 1 calc PR A 2 H18F H 0.2811 0.9462 0.6428 0.055 Uiso 0.105(3) 1 calc PR A 2 C19' C 0.2071(18) 0.799(6) 0.6048(15) 0.0648(17) Uani 0.105(3) 1 d PD A 2 H19D H 0.2115 0.8094 0.5673 0.097 Uiso 0.105(3) 1 calc PR A 2 H19E H 0.1662 0.8370 0.5952 0.097 Uiso 0.105(3) 1 calc PR A 2 H19F H 0.2110 0.6925 0.6170 0.097 Uiso 0.105(3) 1 calc PR A 2 C20' C 0.4215(17) 1.219(7) 0.683(2) 0.080(2) Uani 0.105(3) 1 d PD A 2 H20D H 0.4209 1.1174 0.6669 0.119 Uiso 0.105(3) 1 calc PR A 2 H20E H 0.4125 1.2938 0.6498 0.119 Uiso 0.105(3) 1 calc PR A 2 H20F H 0.3899 1.2265 0.6956 0.119 Uiso 0.105(3) 1 calc PR A 2 O6' O 0.4814(11) 1.249(3) 0.7363(15) 0.0578(10) Uani 0.105(3) 1 d PD . 2 H6OB H 0.4776 1.2946 0.7644 0.069 Uiso 0.105(3) 1 d PR A 2 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 0.0283(3) 0.0251(3) 0.0221(3) 0.0025(2) 0.0120(2) 0.0028(2) O1 0.039(2) 0.041(2) 0.031(2) 0.0077(18) 0.0209(18) 0.0069(18) O2 0.0349(14) 0.0364(15) 0.0264(13) 0.0078(12) 0.0170(12) 0.0112(12) O3 0.0503(18) 0.085(3) 0.0439(17) 0.0248(17) 0.0335(16) 0.0294(18) O4 0.0407(15) 0.0272(15) 0.0438(17) -0.0041(13) 0.0197(14) -0.0023(13) O5 0.056(2) 0.0411(19) 0.056(2) -0.0170(16) 0.0170(17) -0.0133(16) N1 0.0282(15) 0.0264(17) 0.0206(15) 0.0000(13) 0.0115(13) 0.0002(13) N2 0.0300(16) 0.0301(18) 0.0269(16) -0.0003(14) 0.0144(14) -0.0021(14) N3 0.0272(15) 0.0265(17) 0.0236(15) -0.0017(13) 0.0102(13) 0.0038(13) C1 0.0315(19) 0.036(2) 0.0259(19) -0.0021(17) 0.0140(16) -0.0006(17) C2 0.038(2) 0.039(2) 0.036(2) -0.013(2) 0.0194(19) -0.0093(19) C3 0.051(2) 0.032(2) 0.041(2) -0.0049(19) 0.030(2) -0.0036(19) C4 0.042(2) 0.029(2) 0.034(2) 0.0024(17) 0.0226(19) 0.0035(18) C5 0.0326(19) 0.030(2) 0.0232(18) -0.0017(16) 0.0166(16) 0.0021(17) C6 0.0316(19) 0.027(2) 0.0223(17) 0.0017(16) 0.0132(16) 0.0070(16) C7 0.0288(18) 0.025(2) 0.0234(18) -0.0033(16) 0.0095(15) 0.0021(16) C8 0.032(2) 0.037(2) 0.033(2) -0.0004(18) 0.0120(17) 0.0060(18) C9 0.030(2) 0.045(3) 0.044(2) -0.002(2) 0.0176(19) 0.0040(19) C10 0.037(2) 0.049(3) 0.045(2) -0.005(2) 0.027(2) -0.006(2) C11 0.036(2) 0.034(2) 0.037(2) -0.0007(18) 0.0212(18) -0.0038(18) C12 0.040(2) 0.033(2) 0.0231(18) 0.0045(17) 0.0176(17) 0.0074(18) C13 0.035(2) 0.038(2) 0.0253(19) 0.0036(17) 0.0153(17) 0.0069(18) C14 0.036(2) 0.034(2) 0.030(2) -0.0030(18) 0.0110(17) 0.0053(18) C15 0.031(2) 0.036(2) 0.042(2) -0.009(2) 0.0153(19) 0.0015(18) O7 0.048(2) 0.097(3) 0.073(3) 0.010(2) 0.022(2) 0.014(2) C21 0.112(6) 0.119(7) 0.092(5) 0.004(5) 0.044(5) -0.051(5) C16 0.028(3) 0.024(3) 0.0241(19) 0.0015(19) 0.0098(17) 0.0027(18) C17 0.037(2) 0.035(2) 0.027(2) 0.0089(19) 0.0166(19) 0.008(2) C18 0.055(3) 0.052(3) 0.040(3) 0.018(2) 0.031(2) 0.019(3) C19 0.073(4) 0.092(5) 0.051(3) 0.006(3) 0.047(3) 0.002(4) O6 0.041(2) 0.050(2) 0.063(2) 0.011(2) 0.0120(18) -0.0033(17) C20 0.070(4) 0.080(5) 0.076(5) 0.006(4) 0.027(4) -0.002(4) C16' 0.028(3) 0.024(3) 0.0241(19) 0.0015(19) 0.0098(17) 0.0027(18) C17' 0.037(2) 0.035(2) 0.027(2) 0.0089(19) 0.0166(19) 0.008(2) C18' 0.055(3) 0.052(3) 0.040(3) 0.018(2) 0.031(2) 0.019(3) C19' 0.073(4) 0.092(5) 0.051(3) 0.006(3) 0.047(3) 0.002(4) C20' 0.070(4) 0.080(5) 0.076(5) 0.006(4) 0.027(4) -0.002(4) O6' 0.041(2) 0.050(2) 0.063(2) 0.011(2) 0.0120(18) -0.0033(17) _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 1.7718(5) . ? Fe1 O2 1.985(2) . ? Fe1 O4 1.990(3) . ? Fe1 N2 2.148(3) . ? Fe1 N1 2.196(3) . ? Fe1 N3 2.228(3) . ? O1 Fe1 1.7718(5) 5_667 ? O2 C13 1.285(4) . ? O3 C13 1.219(4) . ? O4 C15 1.291(5) . ? O5 C15 1.234(5) . ? N1 C1 1.335(5) . ? N1 C5 1.350(5) . ? N2 C11 1.336(5) . ? N2 C7 1.346(5) . ? N3 C12 1.480(4) . ? N3 C14 1.486(5) . ? N3 C6 1.514(4) . ? C1 C2 1.385(6) . ? C1 H1A 0.9500 . ? C2 C3 1.370(6) . ? C2 H2A 0.9500 . ? C3 C4 1.389(6) . ? C3 H3A 0.9500 . ? C4 C5 1.383(5) . ? C4 H4A 0.9500 . ? C5 C6 1.528(5) . ? C6 C16' 1.537(6) . ? C6 C16 1.537(5) . ? C6 C7 1.551(5) . ? C7 C8 1.376(5) . ? C8 C9 1.383(5) . ? C8 H8A 0.9500 . ? C9 C10 1.381(6) . ? C9 H9A 0.9500 . ? C10 C11 1.388(6) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C12 C13 1.529(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C14 C15 1.511(6) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? O7 C21 1.383(8) . ? O7 H7O 0.8400 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C16 C17 1.527(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.523(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.495(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? O6 C20 1.381(8) . ? O6 H6OA 0.8400 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C16' C17' 1.526(8) . ? C16' H16E 0.9900 . ? C16' H16F 0.9900 . ? C17' C18' 1.524(7) . ? C17' H17E 0.9900 . ? C17' H17F 0.9900 . ? C18' C19' 1.495(8) . ? C18' H18E 0.9900 . ? C18' H18F 0.9900 . ? C19' H19D 0.9800 . ? C19' H19E 0.9800 . ? C19' H19F 0.9800 . ? C20' O6' 1.43(2) . ? C20' H20D 0.9800 . ? C20' H20E 0.9800 . ? C20' H20F 0.9800 . ? O6' O6' 0.83(5) 2_656 ? O6' H6OB 0.8399 . ? 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 O2 102.29(7) . . ? O1 Fe1 O4 104.34(9) . . ? O2 Fe1 O4 93.37(12) . . ? O1 Fe1 N2 98.99(8) . . ? O2 Fe1 N2 157.28(11) . . ? O4 Fe1 N2 88.97(12) . . ? O1 Fe1 N1 102.22(7) . . ? O2 Fe1 N1 88.36(11) . . ? O4 Fe1 N1 152.35(11) . . ? N2 Fe1 N1 79.40(11) . . ? O1 Fe1 N3 173.95(8) . . ? O2 Fe1 N3 81.53(10) . . ? O4 Fe1 N3 79.95(11) . . ? N2 Fe1 N3 76.64(11) . . ? N1 Fe1 N3 73.02(11) . . ? Fe1 O1 Fe1 179.995(1) 5_667 . ? C13 O2 Fe1 118.7(2) . . ? C15 O4 Fe1 119.8(3) . . ? C1 N1 C5 119.7(3) . . ? C1 N1 Fe1 125.5(2) . . ? C5 N1 Fe1 114.8(2) . . ? C11 N2 C7 120.1(3) . . ? C11 N2 Fe1 124.7(3) . . ? C7 N2 Fe1 115.2(2) . . ? C12 N3 C14 111.8(3) . . ? C12 N3 C6 115.6(3) . . ? C14 N3 C6 113.5(3) . . ? C12 N3 Fe1 104.7(2) . . ? C14 N3 Fe1 107.8(2) . . ? C6 N3 Fe1 102.26(19) . . ? N1 C1 C2 122.0(4) . . ? N1 C1 H1A 119.0 . . ? C2 C1 H1A 119.0 . . ? C3 C2 C1 118.4(4) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 120.1(4) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C5 C4 C3 118.6(4) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? N1 C5 C4 121.0(3) . . ? N1 C5 C6 113.8(3) . . ? C4 C5 C6 125.1(3) . . ? N3 C6 C5 105.0(3) . . ? N3 C6 C16' 109(2) . . ? C5 C6 C16' 129.4(14) . . ? N3 C6 C16 115.6(3) . . ? C5 C6 C16 113.3(3) . . ? C16' C6 C16 16.4(14) . . ? N3 C6 C7 106.3(3) . . ? C5 C6 C7 104.2(3) . . ? C16' C6 C7 101(2) . . ? C16 C6 C7 111.5(3) . . ? N2 C7 C8 121.5(3) . . ? N2 C7 C6 113.9(3) . . ? C8 C7 C6 124.5(3) . . ? C7 C8 C9 118.5(4) . . ? C7 C8 H8A 120.8 . . ? C9 C8 H8A 120.8 . . ? C10 C9 C8 120.2(4) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? C9 C10 C11 118.2(4) . . ? C9 C10 H10A 120.9 . . ? C11 C10 H10A 120.9 . . ? N2 C11 C10 121.4(4) . . ? N2 C11 H11A 119.3 . . ? C10 C11 H11A 119.3 . . ? N3 C12 C13 114.4(3) . . ? N3 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? N3 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? O3 C13 O2 125.0(4) . . ? O3 C13 C12 117.4(3) . . ? O2 C13 C12 117.5(3) . . ? N3 C14 C15 112.3(3) . . ? N3 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? N3 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? O5 C15 O4 123.9(4) . . ? O5 C15 C14 117.4(4) . . ? O4 C15 C14 118.7(4) . . ? C21 O7 H7O 109.5 . . ? O7 C21 H21A 109.5 . . ? O7 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O7 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C16 C6 119.3(4) . . ? C17 C16 H16A 107.5 . . ? C6 C16 H16A 107.5 . . ? C17 C16 H16B 107.5 . . ? C6 C16 H16B 107.5 . . ? H16A C16 H16B 107.0 . . ? C18 C17 C16 111.1(4) . . ? C18 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? C18 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? C19 C18 C17 109.7(4) . . ? C19 C18 H18A 109.7 . . ? C17 C18 H18A 109.7 . . ? C19 C18 H18B 109.7 . . ? C17 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C20 O6 H6OA 109.5 . . ? C17' C16' C6 130(2) . . ? C17' C16' H16E 104.8 . . ? C6 C16' H16E 104.8 . . ? C17' C16' H16F 104.8 . . ? C6 C16' H16F 104.8 . . ? H16E C16' H16F 105.8 . . ? C18' C17' C16' 112.5(17) . . ? C18' C17' H17E 109.1 . . ? C16' C17' H17E 109.1 . . ? C18' C17' H17F 109.1 . . ? C16' C17' H17F 109.1 . . ? H17E C17' H17F 107.8 . . ? C19' C18' C17' 109(2) . . ? C19' C18' H18E 109.8 . . ? C17' C18' H18E 109.8 . . ? C19' C18' H18F 109.8 . . ? C17' C18' H18F 109.8 . . ? H18E C18' H18F 108.3 . . ? C18' C19' H19D 109.5 . . ? C18' C19' H19E 109.5 . . ? H19D C19' H19E 109.5 . . ? C18' C19' H19F 109.5 . . ? H19D C19' H19F 109.5 . . ? H19E C19' H19F 109.5 . . ? O6' C20' H20D 109.5 . . ? O6' C20' H20E 109.5 . . ? H20D C20' H20E 109.5 . . ? O6' C20' H20F 109.5 . . ? H20D C20' H20F 109.5 . . ? H20E C20' H20F 109.5 . . ? O6' O6' C20' 166(5) 2_656 . ? O6' O6' H6OB 83.1 2_656 . ? C20' O6' H6OB 110.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Fe1 O1 Fe1 22(3) . . . 5_667 ? O4 Fe1 O1 Fe1 119(3) . . . 5_667 ? N2 Fe1 O1 Fe1 -150(3) . . . 5_667 ? N1 Fe1 O1 Fe1 -69(3) . . . 5_667 ? N3 Fe1 O1 Fe1 -107(3) . . . 5_667 ? O1 Fe1 O2 C13 -166.0(3) . . . . ? O4 Fe1 O2 C13 88.6(3) . . . . ? N2 Fe1 O2 C13 -6.8(5) . . . . ? N1 Fe1 O2 C13 -63.8(3) . . . . ? N3 Fe1 O2 C13 9.3(3) . . . . ? O1 Fe1 O4 C15 171.3(3) . . . . ? O2 Fe1 O4 C15 -85.1(3) . . . . ? N2 Fe1 O4 C15 72.3(3) . . . . ? N1 Fe1 O4 C15 7.8(4) . . . . ? N3 Fe1 O4 C15 -4.4(3) . . . . ? O1 Fe1 N1 C1 28.5(3) . . . . ? O2 Fe1 N1 C1 -73.7(3) . . . . ? O4 Fe1 N1 C1 -167.9(3) . . . . ? N2 Fe1 N1 C1 125.5(3) . . . . ? N3 Fe1 N1 C1 -155.4(3) . . . . ? O1 Fe1 N1 C5 -149.7(2) . . . . ? O2 Fe1 N1 C5 108.1(2) . . . . ? O4 Fe1 N1 C5 13.9(4) . . . . ? N2 Fe1 N1 C5 -52.7(2) . . . . ? N3 Fe1 N1 C5 26.4(2) . . . . ? O1 Fe1 N2 C11 -23.8(3) . . . . ? O2 Fe1 N2 C11 176.9(3) . . . . ? O4 Fe1 N2 C11 80.6(3) . . . . ? N1 Fe1 N2 C11 -124.6(3) . . . . ? N3 Fe1 N2 C11 160.5(3) . . . . ? O1 Fe1 N2 C7 158.3(2) . . . . ? O2 Fe1 N2 C7 -1.0(5) . . . . ? O4 Fe1 N2 C7 -97.3(3) . . . . ? N1 Fe1 N2 C7 57.5(3) . . . . ? N3 Fe1 N2 C7 -17.4(2) . . . . ? O1 Fe1 N3 C12 114.9(7) . . . . ? O2 Fe1 N3 C12 -14.6(2) . . . . ? O4 Fe1 N3 C12 -109.6(2) . . . . ? N2 Fe1 N3 C12 159.1(2) . . . . ? N1 Fe1 N3 C12 76.3(2) . . . . ? O1 Fe1 N3 C14 -125.9(7) . . . . ? O2 Fe1 N3 C14 104.6(2) . . . . ? O4 Fe1 N3 C14 9.6(2) . . . . ? N2 Fe1 N3 C14 -81.7(2) . . . . ? N1 Fe1 N3 C14 -164.5(2) . . . . ? O1 Fe1 N3 C6 -6.1(9) . . . . ? O2 Fe1 N3 C6 -135.6(2) . . . . ? O4 Fe1 N3 C6 129.4(2) . . . . ? N2 Fe1 N3 C6 38.1(2) . . . . ? N1 Fe1 N3 C6 -44.7(2) . . . . ? C5 N1 C1 C2 -0.1(5) . . . . ? Fe1 N1 C1 C2 -178.2(3) . . . . ? N1 C1 C2 C3 1.7(5) . . . . ? C1 C2 C3 C4 -1.4(5) . . . . ? C2 C3 C4 C5 -0.5(5) . . . . ? C1 N1 C5 C4 -2.0(5) . . . . ? Fe1 N1 C5 C4 176.3(3) . . . . ? C1 N1 C5 C6 -179.0(3) . . . . ? Fe1 N1 C5 C6 -0.7(3) . . . . ? C3 C4 C5 N1 2.2(5) . . . . ? C3 C4 C5 C6 178.9(3) . . . . ? C12 N3 C6 C5 -55.7(3) . . . . ? C14 N3 C6 C5 173.2(3) . . . . ? Fe1 N3 C6 C5 57.4(3) . . . . ? C12 N3 C6 C16' 86(2) . . . . ? C14 N3 C6 C16' -45(2) . . . . ? Fe1 N3 C6 C16' -161(2) . . . . ? C12 N3 C6 C16 69.9(4) . . . . ? C14 N3 C6 C16 -61.2(4) . . . . ? Fe1 N3 C6 C16 -177.0(3) . . . . ? C12 N3 C6 C7 -165.7(3) . . . . ? C14 N3 C6 C7 63.2(3) . . . . ? Fe1 N3 C6 C7 -52.6(3) . . . . ? N1 C5 C6 N3 -39.1(4) . . . . ? C4 C5 C6 N3 144.0(3) . . . . ? N1 C5 C6 C16' -170(4) . . . . ? C4 C5 C6 C16' 13(4) . . . . ? N1 C5 C6 C16 -166.1(4) . . . . ? C4 C5 C6 C16 17.0(5) . . . . ? N1 C5 C6 C7 72.5(3) . . . . ? C4 C5 C6 C7 -104.4(4) . . . . ? C11 N2 C7 C8 -3.3(5) . . . . ? Fe1 N2 C7 C8 174.7(3) . . . . ? C11 N2 C7 C6 173.5(3) . . . . ? Fe1 N2 C7 C6 -8.5(4) . . . . ? N3 C6 C7 N2 43.0(4) . . . . ? C5 C6 C7 N2 -67.6(4) . . . . ? C16' C6 C7 N2 156.7(18) . . . . ? C16 C6 C7 N2 169.8(3) . . . . ? N3 C6 C7 C8 -140.4(4) . . . . ? C5 C6 C7 C8 109.0(4) . . . . ? C16' C6 C7 C8 -26.7(18) . . . . ? C16 C6 C7 C8 -13.5(5) . . . . ? N2 C7 C8 C9 2.6(6) . . . . ? C6 C7 C8 C9 -173.8(4) . . . . ? C7 C8 C9 C10 0.0(6) . . . . ? C8 C9 C10 C11 -1.9(6) . . . . ? C7 N2 C11 C10 1.2(6) . . . . ? Fe1 N2 C11 C10 -176.6(3) . . . . ? C9 C10 C11 N2 1.3(6) . . . . ? C14 N3 C12 C13 -98.3(4) . . . . ? C6 N3 C12 C13 129.8(3) . . . . ? Fe1 N3 C12 C13 18.1(4) . . . . ? Fe1 O2 C13 O3 176.5(3) . . . . ? Fe1 O2 C13 C12 -1.1(5) . . . . ? N3 C12 C13 O3 169.0(4) . . . . ? N3 C12 C13 O2 -13.2(5) . . . . ? C12 N3 C14 C15 101.5(4) . . . . ? C6 N3 C14 C15 -125.5(3) . . . . ? Fe1 N3 C14 C15 -13.1(4) . . . . ? Fe1 O4 C15 O5 179.5(3) . . . . ? Fe1 O4 C15 C14 -2.3(5) . . . . ? N3 C14 C15 O5 -170.5(3) . . . . ? N3 C14 C15 O4 11.2(5) . . . . ? N3 C6 C16 C17 -51.6(5) . . . . ? C5 C6 C16 C17 69.6(5) . . . . ? C16' C6 C16 C17 -121(10) . . . . ? C7 C6 C16 C17 -173.2(4) . . . . ? C6 C16 C17 C18 -175.5(4) . . . . ? C16 C17 C18 C19 -176.4(5) . . . . ? N3 C6 C16' C17' 48(7) . . . . ? C5 C6 C16' C17' 177(4) . . . . ? C16 C6 C16' C17' 164(16) . . . . ? C7 C6 C16' C17' -64(6) . . . . ? C6 C16' C17' C18' 171(5) . . . . ? C16' C17' C18' C19' 175(4) . . . . ? 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 O7 H7O O3 0.84 1.97 2.785(5) 164.9 . O6 H6OA O5 0.84 1.85 2.685(5) 176.1 3 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.752 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.082