# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Norrild, Jens Chr' 'Sotofte, Inger' _publ_contact_author_name 'Dr Jens Chr Norrild' _publ_contact_author_address ; Dr Jens Chr Norrild Department of Chemistry University of Copenhagen Laboratory for Organic Chemistry Universitetsparken 5 Copenhagen DK 2100 DENMARK ; _publ_contact_author_email 'JCN@KIKU.DK' data_B102377M-2 _database_code_CSD 160671 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H20 B Fe N O2' _chemical_formula_weight 300.97 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.2501(15) _cell_length_b 16.807(3) _cell_length_c 23.309(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2840.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method ? _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 1.058 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20153 _diffrn_reflns_av_R_equivalents 0.1404 _diffrn_reflns_av_sigmaI/netI 0.2303 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 29.74 _reflns_number_total 7330 _reflns_number_observed 3819 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0300P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_number_reflns 7330 _refine_ls_number_parameters 349 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1659 _refine_ls_R_factor_obs 0.0664 _refine_ls_wR_factor_all 0.1143 _refine_ls_wR_factor_obs 0.0921 _refine_ls_goodness_of_fit_all 0.930 _refine_ls_goodness_of_fit_obs 1.059 _refine_ls_restrained_S_all 0.930 _refine_ls_restrained_S_obs 1.059 _refine_ls_shift/esd_max -0.268 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Fe1 Fe 0.35804(11) 0.12722(4) 0.80128(3) 0.0168(2) Uani 1 d . . C1 C 0.5307(8) 0.2149(3) 0.7724(2) 0.0133(12) Uani 1 d . . C2 C 0.6017(8) 0.1380(3) 0.7591(2) 0.0197(14) Uani 1 d . . H2 H 0.7224(8) 0.1164(3) 0.7728(2) 0.024 Uiso 1 calc R . C3 C 0.4745(8) 0.0961(3) 0.7247(2) 0.0186(13) Uani 1 d . . H3 H 0.4897(8) 0.0408(3) 0.7096(2) 0.022 Uiso 1 calc R . C4 C 0.3220(8) 0.1461(3) 0.7159(2) 0.0211(14) Uani 1 d . . H4 H 0.2090(8) 0.1323(3) 0.6934(2) 0.025 Uiso 1 calc R . C5 C 0.3544(8) 0.2196(3) 0.7449(2) 0.0135(12) Uani 1 d . . B1 B 0.6346(9) 0.2794(4) 0.8071(3) 0.0194(14) Uani 1 d . . O1 O 0.6050(5) 0.3588(2) 0.79756(15) 0.0228(9) Uani 1 d . . H1O H 0.5210(5) 0.3644(2) 0.77308(15) 0.027 Uiso 1 calc R . O2 O 0.7640(5) 0.2565(2) 0.84672(15) 0.0198(9) Uani 1 d . . H2O H 0.8005(5) 0.2966(2) 0.86505(15) 0.024 Uiso 1 calc R . C6 C 0.2282(8) 0.2910(3) 0.7463(2) 0.0167(13) Uani 1 d . . H6 H 0.2075(8) 0.3044(3) 0.7875(2) 0.020 Uiso 1 calc R . C7 C 0.0406(8) 0.2744(3) 0.7203(2) 0.0227(14) Uani 1 d . . H71 H -0.0168(8) 0.2294(3) 0.7402(2) 0.027 Uiso 1 calc R . H72 H 0.0548(8) 0.2615(3) 0.6795(2) 0.027 Uiso 1 calc R . H73 H -0.0377(8) 0.3216(3) 0.7243(2) 0.027 Uiso 1 calc R . N1 N 0.3300(6) 0.3597(2) 0.7201(2) 0.0186(11) Uani 1 d . . C8 C 0.3851(8) 0.3449(3) 0.6603(2) 0.0239(15) Uani 1 d . . H81 H 0.4648(8) 0.2978(3) 0.6587(2) 0.029 Uiso 1 calc R . H82 H 0.4523(8) 0.3911(3) 0.6455(2) 0.029 Uiso 1 calc R . H83 H 0.2749(8) 0.3358(3) 0.6368(2) 0.029 Uiso 1 calc R . C9 C 0.2244(8) 0.4346(3) 0.7243(2) 0.027(2) Uani 1 d . . H91 H 0.1936(8) 0.4451(3) 0.7645(2) 0.033 Uiso 1 calc R . H92 H 0.1106(8) 0.4300(3) 0.7019(2) 0.033 Uiso 1 calc R . H93 H 0.2989(8) 0.4786(3) 0.7092(2) 0.033 Uiso 1 calc R . C10 C 0.1634(10) 0.1495(4) 0.8622(3) 0.036(2) Uani 1 d . . H10 H 0.0864(10) 0.1987(4) 0.8655(3) 0.043 Uiso 1 calc R . C11 C 0.3388(9) 0.1367(3) 0.8882(2) 0.0283(15) Uani 1 d . . H11 H 0.4076(9) 0.1750(3) 0.9131(2) 0.034 Uiso 1 calc R . C12 C 0.3978(8) 0.0587(3) 0.8720(2) 0.0231(15) Uani 1 d . . H12 H 0.5163(8) 0.0328(3) 0.8834(2) 0.028 Uiso 1 calc R . C13 C 0.2616(9) 0.0252(4) 0.8368(3) 0.031(2) Uani 1 d . . H13 H 0.2666(9) -0.0288(4) 0.8189(3) 0.037 Uiso 1 calc R . C14 C 0.1188(9) 0.0802(4) 0.8304(3) 0.038(2) Uani 1 d . . H14 H 0.0043(9) 0.0721(4) 0.8073(3) 0.045 Uiso 1 calc R . Fe2 Fe 0.03240(11) 0.61186(5) 0.94587(3) 0.0165(2) Uani 1 d . . C15 C 0.1104(7) 0.5175(3) 0.8962(2) 0.0171(13) Uani 1 d . . C16 C 0.1451(8) 0.5905(3) 0.8675(2) 0.0203(14) Uani 1 d . . H16 H 0.0912(8) 0.6069(3) 0.8298(2) 0.024 Uiso 1 calc R . C17 C 0.2688(7) 0.6364(3) 0.9013(2) 0.0220(14) Uani 1 d . . H17 H 0.3160(7) 0.6906(3) 0.8916(2) 0.026 Uiso 1 calc R . C18 C 0.3090(7) 0.5933(3) 0.9519(2) 0.0213(14) Uani 1 d . . H18 H 0.3910(7) 0.6111(3) 0.9839(2) 0.026 Uiso 1 calc R . C19 C 0.2135(7) 0.5204(3) 0.9487(2) 0.0145(12) Uani 1 d . . B2 B -0.0280(9) 0.4534(4) 0.8738(2) 0.0152(14) Uani 1 d . . O3 O -0.0181(5) 0.3769(2) 0.89285(14) 0.0250(9) Uani 1 d D . H3O H 0.0687(54) 0.3647(34) 0.9123(19) 0.030 Uiso 1 d D . O4 O -0.1501(6) 0.4750(2) 0.8338(2) 0.0270(10) Uani 1 d D . H4O H -0.2132(68) 0.4407(26) 0.8184(21) 0.032 Uiso 1 d D . C20 C 0.2173(8) 0.4543(3) 0.9934(2) 0.0188(14) Uani 1 d . . H20 H 0.0879(8) 0.4477(3) 1.0075(2) 0.023 Uiso 1 calc R . C21 C 0.3344(8) 0.4764(3) 1.0454(2) 0.0244(14) Uani 1 d . . H211 H 0.2758(8) 0.5204(3) 1.0661(2) 0.029 Uiso 1 calc R . H212 H 0.4575(8) 0.4927(3) 1.0326(2) 0.029 Uiso 1 calc R . H213 H 0.3451(8) 0.4303(3) 1.0709(2) 0.029 Uiso 1 calc R . N2 N 0.2697(6) 0.3785(3) 0.9654(2) 0.0201(11) Uani 1 d . . C22 C 0.4536(8) 0.3794(4) 0.9395(2) 0.036(2) Uani 1 d . . H221 H 0.5450(8) 0.3943(4) 0.9685(2) 0.043 Uiso 1 calc R . H222 H 0.4563(8) 0.4181(4) 0.9080(2) 0.043 Uiso 1 calc R . H223 H 0.4826(8) 0.3263(4) 0.9245(2) 0.043 Uiso 1 calc R . C23 C 0.2569(9) 0.3108(3) 1.0049(2) 0.030(2) Uani 1 d . . H231 H 0.1331(9) 0.3090(3) 1.0218(2) 0.036 Uiso 1 calc R . H232 H 0.3487(9) 0.3168(3) 1.0355(2) 0.036 Uiso 1 calc R . H233 H 0.2803(9) 0.2613(3) 0.9839(2) 0.036 Uiso 1 calc R . C24 C -0.2129(8) 0.6672(4) 0.9330(2) 0.030(2) Uani 1 d . . H24 H -0.2704(8) 0.6797(4) 0.8951(2) 0.036 Uiso 1 calc R . C25 C -0.0930(9) 0.7168(3) 0.9645(2) 0.028(2) Uani 1 d . . H25 H -0.0491(9) 0.7707(3) 0.9524(2) 0.034 Uiso 1 calc R . C26 C -0.0436(9) 0.6780(3) 1.0148(2) 0.030(2) Uani 1 d . . H26 H 0.0407(9) 0.6991(3) 1.0451(2) 0.036 Uiso 1 calc R . C27 C -0.1340(8) 0.6042(3) 1.0157(2) 0.0276(15) Uani 1 d . . H27 H -0.1254(8) 0.5634(3) 1.0469(2) 0.033 Uiso 1 calc R . C28 C -0.2360(8) 0.5970(3) 0.9646(3) 0.028(2) Uani 1 d . . H28 H -0.3139(8) 0.5505(3) 0.9533(3) 0.034 Uiso 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 0.0174(4) 0.0143(4) 0.0186(4) 0.0022(4) -0.0009(4) -0.0008(4) C1 0.012(3) 0.009(3) 0.019(3) 0.003(2) 0.001(3) -0.003(3) C2 0.025(4) 0.016(3) 0.018(3) 0.008(3) 0.000(3) -0.007(3) C3 0.024(3) 0.005(3) 0.027(3) -0.003(2) -0.002(3) -0.001(3) C4 0.024(4) 0.022(3) 0.018(3) 0.001(2) -0.002(3) 0.003(3) C5 0.016(3) 0.013(3) 0.012(3) 0.003(2) -0.002(3) 0.005(3) B1 0.016(4) 0.016(3) 0.025(4) 0.003(3) 0.005(4) 0.002(3) O1 0.023(2) 0.020(2) 0.026(2) -0.001(2) -0.008(2) -0.004(2) O2 0.019(2) 0.014(2) 0.027(2) -0.005(2) -0.010(2) 0.003(2) C6 0.022(4) 0.016(3) 0.012(3) 0.000(2) 0.002(3) -0.002(3) C7 0.017(3) 0.017(3) 0.035(4) 0.005(3) 0.000(3) -0.002(3) N1 0.022(3) 0.013(3) 0.021(2) 0.004(2) -0.001(2) 0.002(2) C8 0.031(4) 0.018(3) 0.022(3) 0.001(2) 0.005(3) -0.008(3) C9 0.026(4) 0.014(3) 0.042(4) 0.000(3) 0.002(3) 0.001(3) C10 0.037(5) 0.037(4) 0.034(4) 0.023(3) 0.022(4) 0.029(4) C11 0.040(4) 0.030(4) 0.015(3) 0.002(3) 0.011(3) -0.001(4) C12 0.024(4) 0.022(3) 0.024(3) 0.006(3) -0.004(3) 0.004(3) C13 0.033(4) 0.018(4) 0.043(4) 0.008(3) -0.004(3) -0.004(3) C14 0.025(4) 0.046(5) 0.043(4) 0.025(3) -0.002(4) 0.001(3) Fe2 0.0143(4) 0.0159(4) 0.0192(4) -0.0030(4) 0.0004(4) 0.0000(4) C15 0.014(3) 0.023(3) 0.014(3) 0.000(2) 0.001(3) 0.006(3) C16 0.022(3) 0.020(3) 0.019(3) 0.000(2) 0.004(3) 0.002(3) C17 0.016(3) 0.024(4) 0.026(3) -0.003(3) 0.011(3) 0.001(3) C18 0.015(3) 0.018(3) 0.031(3) -0.006(3) 0.002(3) -0.001(2) C19 0.009(3) 0.022(3) 0.012(3) 0.001(3) -0.002(3) -0.002(2) B2 0.014(4) 0.019(4) 0.013(3) -0.003(3) 0.009(3) 0.001(3) O3 0.027(2) 0.018(2) 0.030(2) 0.000(2) -0.014(2) 0.002(2) O4 0.034(3) 0.019(2) 0.028(2) 0.000(2) -0.014(2) -0.002(2) C20 0.014(3) 0.026(3) 0.016(3) -0.001(3) 0.002(3) 0.000(3) C21 0.027(4) 0.030(3) 0.017(3) -0.001(3) -0.002(3) 0.008(3) N2 0.028(3) 0.013(3) 0.020(2) -0.001(2) 0.006(2) 0.006(2) C22 0.044(4) 0.031(3) 0.032(3) -0.001(3) 0.011(3) 0.015(4) C23 0.036(4) 0.026(4) 0.029(4) 0.002(3) 0.008(3) -0.002(3) C24 0.025(4) 0.045(4) 0.020(4) -0.005(3) -0.005(3) 0.015(3) C25 0.039(4) 0.018(3) 0.027(4) 0.003(3) 0.012(3) 0.003(3) C26 0.029(4) 0.034(4) 0.029(4) -0.014(3) -0.012(3) 0.006(3) C27 0.030(4) 0.030(4) 0.022(3) 0.012(3) 0.013(3) 0.012(3) C28 0.012(3) 0.029(4) 0.044(4) -0.018(3) 0.004(3) -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 C14 2.024(6) . ? Fe1 C13 2.028(6) . ? Fe1 C12 2.031(5) . ? Fe1 C2 2.030(5) . ? Fe1 C4 2.032(5) . ? Fe1 C5 2.035(5) . ? Fe1 C11 2.036(5) . ? Fe1 C10 2.037(6) . ? Fe1 C3 2.042(5) . ? Fe1 C1 2.047(5) . ? C1 C2 1.426(7) . ? C1 C5 1.432(7) . ? C1 B1 1.548(8) . ? C2 C3 1.409(7) . ? C3 C4 1.404(7) . ? C4 C5 1.428(7) . ? C5 C6 1.508(7) . ? B1 O1 1.370(6) . ? B1 O2 1.371(7) . ? C6 N1 1.499(6) . ? C6 C7 1.515(7) . ? N1 C8 1.473(6) . ? N1 C9 1.477(6) . ? C10 C14 1.418(8) . ? C10 C11 1.425(8) . ? C11 C12 1.429(7) . ? C12 C13 1.401(8) . ? C13 C14 1.395(8) . ? Fe2 C28 2.010(6) . ? Fe2 C19 2.022(5) . ? Fe2 C24 2.029(6) . ? Fe2 C26 2.030(6) . ? Fe2 C27 2.031(5) . ? Fe2 C25 2.032(6) . ? Fe2 C16 2.033(5) . ? Fe2 C18 2.034(5) . ? Fe2 C15 2.044(5) . ? Fe2 C17 2.046(5) . ? C15 C16 1.419(7) . ? C15 C19 1.435(7) . ? C15 B2 1.562(8) . ? C16 C17 1.421(7) . ? C17 C18 1.414(7) . ? C18 C19 1.409(6) . ? C19 C20 1.523(7) . ? B2 O4 1.335(7) . ? B2 O3 1.363(7) . ? C20 N2 1.482(6) . ? C20 C21 1.525(7) . ? N2 C22 1.464(6) . ? N2 C23 1.468(6) . ? C24 C28 1.401(8) . ? C24 C25 1.412(8) . ? C25 C26 1.388(7) . ? C26 C27 1.404(8) . ? C27 C28 1.407(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 Fe1 C13 40.3(2) . . ? C14 Fe1 C12 68.1(2) . . ? C13 Fe1 C12 40.4(2) . . ? C14 Fe1 C2 160.6(2) . . ? C13 Fe1 C2 125.0(2) . . ? C12 Fe1 C2 108.7(2) . . ? C14 Fe1 C4 106.2(2) . . ? C13 Fe1 C4 119.2(2) . . ? C12 Fe1 C4 154.4(2) . . ? C2 Fe1 C4 67.9(2) . . ? C14 Fe1 C5 120.3(2) . . ? C13 Fe1 C5 154.7(2) . . ? C12 Fe1 C5 163.5(2) . . ? C2 Fe1 C5 68.3(2) . . ? C4 Fe1 C5 41.1(2) . . ? C14 Fe1 C11 68.8(2) . . ? C13 Fe1 C11 68.7(2) . . ? C12 Fe1 C11 41.1(2) . . ? C2 Fe1 C11 122.3(2) . . ? C4 Fe1 C11 162.4(2) . . ? C5 Fe1 C11 125.6(2) . . ? C14 Fe1 C10 40.9(2) . . ? C13 Fe1 C10 68.4(2) . . ? C12 Fe1 C10 68.7(2) . . ? C2 Fe1 C10 157.6(3) . . ? C4 Fe1 C10 124.4(2) . . ? C5 Fe1 C10 107.5(2) . . ? C11 Fe1 C10 40.9(2) . . ? C14 Fe1 C3 123.2(3) . . ? C13 Fe1 C3 106.4(2) . . ? C12 Fe1 C3 120.3(2) . . ? C2 Fe1 C3 40.5(2) . . ? C4 Fe1 C3 40.3(2) . . ? C5 Fe1 C3 68.7(2) . . ? C11 Fe1 C3 156.5(2) . . ? C10 Fe1 C3 160.5(3) . . ? C14 Fe1 C1 156.3(2) . . ? C13 Fe1 C1 162.4(2) . . ? C12 Fe1 C1 126.0(2) . . ? C2 Fe1 C1 40.9(2) . . ? C4 Fe1 C1 69.2(2) . . ? C5 Fe1 C1 41.1(2) . . ? C11 Fe1 C1 108.2(2) . . ? C10 Fe1 C1 121.4(2) . . ? C3 Fe1 C1 69.2(2) . . ? C2 C1 C5 106.0(4) . . ? C2 C1 B1 125.0(5) . . ? C5 C1 B1 129.0(5) . . ? C2 C1 Fe1 68.9(3) . . ? C5 C1 Fe1 69.0(3) . . ? B1 C1 Fe1 129.0(4) . . ? C3 C2 C1 109.9(5) . . ? C3 C2 Fe1 70.2(3) . . ? C1 C2 Fe1 70.2(3) . . ? C4 C3 C2 107.4(5) . . ? C4 C3 Fe1 69.5(3) . . ? C2 C3 Fe1 69.3(3) . . ? C3 C4 C5 108.6(5) . . ? C3 C4 Fe1 70.2(3) . . ? C5 C4 Fe1 69.6(3) . . ? C4 C5 C1 108.1(5) . . ? C4 C5 C6 126.7(5) . . ? C1 C5 C6 125.2(5) . . ? C4 C5 Fe1 69.3(3) . . ? C1 C5 Fe1 69.9(3) . . ? C6 C5 Fe1 126.9(4) . . ? O1 B1 O2 119.3(5) . . ? O1 B1 C1 121.4(5) . . ? O2 B1 C1 119.3(5) . . ? N1 C6 C5 107.8(4) . . ? N1 C6 C7 114.9(4) . . ? C5 C6 C7 113.0(4) . . ? C8 N1 C9 110.3(4) . . ? C8 N1 C6 112.8(4) . . ? C9 N1 C6 112.1(4) . . ? C14 C10 C11 107.5(5) . . ? C14 C10 Fe1 69.0(4) . . ? C11 C10 Fe1 69.5(3) . . ? C10 C11 C12 107.1(5) . . ? C10 C11 Fe1 69.6(3) . . ? C12 C11 Fe1 69.2(3) . . ? C13 C12 C11 108.2(5) . . ? C13 C12 Fe1 69.7(3) . . ? C11 C12 Fe1 69.7(3) . . ? C14 C13 C12 108.6(6) . . ? C14 C13 Fe1 69.7(3) . . ? C12 C13 Fe1 69.9(3) . . ? C13 C14 C10 108.6(6) . . ? C13 C14 Fe1 70.0(4) . . ? C10 C14 Fe1 70.1(4) . . ? C28 Fe2 C19 121.8(2) . . ? C28 Fe2 C24 40.6(2) . . ? C19 Fe2 C24 157.2(2) . . ? C28 Fe2 C26 68.5(2) . . ? C19 Fe2 C26 124.5(2) . . ? C24 Fe2 C26 68.2(2) . . ? C28 Fe2 C27 40.8(2) . . ? C19 Fe2 C27 108.1(2) . . ? C24 Fe2 C27 68.1(2) . . ? C26 Fe2 C27 40.4(2) . . ? C28 Fe2 C25 68.2(2) . . ? C19 Fe2 C25 160.6(2) . . ? C24 Fe2 C25 40.7(2) . . ? C26 Fe2 C25 40.0(2) . . ? C27 Fe2 C25 67.5(2) . . ? C28 Fe2 C16 124.2(2) . . ? C19 Fe2 C16 68.5(2) . . ? C24 Fe2 C16 107.5(2) . . ? C26 Fe2 C16 156.5(2) . . ? C27 Fe2 C16 161.4(2) . . ? C25 Fe2 C16 121.7(2) . . ? C28 Fe2 C18 157.0(2) . . ? C19 Fe2 C18 40.6(2) . . ? C24 Fe2 C18 160.8(2) . . ? C26 Fe2 C18 107.3(2) . . ? C27 Fe2 C18 121.4(2) . . ? C25 Fe2 C18 124.0(2) . . ? C16 Fe2 C18 68.8(2) . . ? C28 Fe2 C15 107.1(2) . . ? C19 Fe2 C15 41.3(2) . . ? C24 Fe2 C15 121.0(2) . . ? C26 Fe2 C15 161.6(2) . . ? C27 Fe2 C15 124.7(2) . . ? C25 Fe2 C15 156.8(2) . . ? C16 Fe2 C15 40.7(2) . . ? C18 Fe2 C15 69.3(2) . . ? C28 Fe2 C17 161.2(2) . . ? C19 Fe2 C17 68.0(2) . . ? C24 Fe2 C17 124.5(2) . . ? C26 Fe2 C17 121.3(2) . . ? C27 Fe2 C17 156.6(2) . . ? C25 Fe2 C17 108.0(2) . . ? C16 Fe2 C17 40.8(2) . . ? C18 Fe2 C17 40.5(2) . . ? C15 Fe2 C17 68.7(2) . . ? C16 C15 C19 106.2(5) . . ? C16 C15 B2 123.5(5) . . ? C19 C15 B2 130.0(5) . . ? C16 C15 Fe2 69.2(3) . . ? C19 C15 Fe2 68.5(3) . . ? B2 C15 Fe2 123.2(4) . . ? C15 C16 C17 108.6(5) . . ? C15 C16 Fe2 70.0(3) . . ? C17 C16 Fe2 70.1(3) . . ? C18 C17 C16 108.3(5) . . ? C18 C17 Fe2 69.3(3) . . ? C16 C17 Fe2 69.1(3) . . ? C19 C18 C17 107.5(5) . . ? C19 C18 Fe2 69.2(3) . . ? C17 C18 Fe2 70.2(3) . . ? C18 C19 C15 109.3(5) . . ? C18 C19 C20 126.1(5) . . ? C15 C19 C20 124.6(4) . . ? C18 C19 Fe2 70.1(3) . . ? C15 C19 Fe2 70.1(3) . . ? C20 C19 Fe2 126.0(4) . . ? O4 B2 O3 121.2(5) . . ? O4 B2 C15 118.2(5) . . ? O3 B2 C15 120.5(5) . . ? N2 C20 C19 109.3(4) . . ? N2 C20 C21 114.6(4) . . ? C19 C20 C21 112.1(4) . . ? C22 N2 C23 108.9(5) . . ? C22 N2 C20 114.0(5) . . ? C23 N2 C20 112.0(4) . . ? C28 C24 C25 107.3(5) . . ? C28 C24 Fe2 69.0(3) . . ? C25 C24 Fe2 69.8(3) . . ? C26 C25 C24 108.7(5) . . ? C26 C25 Fe2 69.9(3) . . ? C24 C25 Fe2 69.6(3) . . ? C25 C26 C27 108.0(5) . . ? C25 C26 Fe2 70.1(3) . . ? C27 C26 Fe2 69.8(3) . . ? C26 C27 C28 107.9(5) . . ? C26 C27 Fe2 69.7(3) . . ? C28 C27 Fe2 68.8(3) . . ? C24 C28 C27 108.1(5) . . ? C24 C28 Fe2 70.4(4) . . ? C27 C28 Fe2 70.4(3) . . ? _refine_diff_density_max 0.449 _refine_diff_density_min -0.655 _refine_diff_density_rms 0.110 #===END data_B102377M-3 _database_code_CSD 160672 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C40 H38 B Fe N O2' _chemical_formula_weight 631.37 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.866(2) _cell_length_b 13.168(3) _cell_length_c 11.968(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.55(3) _cell_angle_gamma 90.00 _cell_volume 1553.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method ? _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.523 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10719 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 29.45 _reflns_number_total 6715 _reflns_number_observed 6224 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.2853P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.025(10) _refine_ls_number_reflns 6715 _refine_ls_number_parameters 406 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_obs 0.0310 _refine_ls_wR_factor_all 0.0728 _refine_ls_wR_factor_obs 0.0707 _refine_ls_goodness_of_fit_all 1.036 _refine_ls_goodness_of_fit_obs 1.048 _refine_ls_restrained_S_all 1.036 _refine_ls_restrained_S_obs 1.047 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Fe Fe 0.91739(3) 0.74627(2) 0.50053(2) 0.01976(7) Uani 1 d . . C1 C 0.9053(2) 0.81252(15) 0.3463(2) 0.0178(4) Uani 1 d . . C2 C 1.0161(2) 0.8540(2) 0.4131(2) 0.0215(4) Uani 1 d . . H2 H 1.0271(2) 0.9270(2) 0.4349(2) 0.026 Uiso 1 calc R . C3 C 1.1064(2) 0.77480(15) 0.4437(2) 0.0263(5) Uani 1 d . . H3 H 1.1917(2) 0.78202(15) 0.4913(2) 0.032 Uiso 1 calc R . C4 C 1.0544(2) 0.6826(2) 0.3972(2) 0.0237(4) Uani 1 d . . H4 H 1.0969(2) 0.6140(2) 0.4063(2) 0.028 Uiso 1 calc R . C5 C 0.9295(2) 0.7048(2) 0.3369(2) 0.0182(4) Uani 1 d . . B B 0.7825(2) 0.8756(2) 0.3057(2) 0.0165(4) Uani 1 d . . O1 O 0.66394(13) 0.84015(9) 0.25477(10) 0.0160(3) Uani 1 d . . O2 O 0.78328(14) 0.97981(9) 0.31625(10) 0.0176(3) Uani 1 d . . C6 C 0.5940(2) 0.92768(13) 0.20647(14) 0.0154(3) Uani 1 d . . C7 C 0.6456(2) 1.01488(13) 0.29041(15) 0.0167(4) Uani 1 d . . C8 C 0.6534(2) 1.11963(14) 0.2375(2) 0.0184(4) Uani 1 d . . C9 C 0.5468(2) 1.18852(15) 0.2435(2) 0.0239(4) Uani 1 d . . H9 H 0.4715(2) 1.17283(15) 0.2872(2) 0.029 Uiso 1 calc R . C10 C 0.5497(3) 1.2803(2) 0.1856(2) 0.0296(5) Uani 1 d . . H10 H 0.4755(3) 1.3260(2) 0.1884(2) 0.035 Uiso 1 calc R . C11 C 0.6602(3) 1.3048(2) 0.1245(2) 0.0326(5) Uani 1 d . . H11 H 0.6613(3) 1.3668(2) 0.0838(2) 0.039 Uiso 1 calc R . C12 C 0.7698(2) 1.2389(2) 0.1222(2) 0.0281(4) Uani 1 d . . H12 H 0.8474(2) 1.2568(2) 0.0824(2) 0.034 Uiso 1 calc R . C13 C 0.7658(2) 1.14686(15) 0.1782(2) 0.0213(4) Uani 1 d . . H13 H 0.8408(2) 1.10181(15) 0.1759(2) 0.026 Uiso 1 calc R . C14 C 0.5786(2) 1.01532(14) 0.4035(2) 0.0175(4) Uani 1 d . . C15 C 0.4985(2) 0.9378(2) 0.4424(2) 0.0217(4) Uani 1 d . . H15 H 0.4736(2) 0.8829(2) 0.3942(2) 0.026 Uiso 1 calc R . C16 C 0.4539(2) 0.9391(2) 0.5512(2) 0.0247(4) Uani 1 d . . H16 H 0.3992(2) 0.8851(2) 0.5765(2) 0.030 Uiso 1 calc R . C17 C 0.4884(2) 1.0179(2) 0.6223(2) 0.0282(5) Uani 1 d . . H17 H 0.4566(2) 1.0190(2) 0.6961(2) 0.034 Uiso 1 calc R . C18 C 0.5696(3) 1.0954(2) 0.5855(2) 0.0313(5) Uani 1 d . . H18 H 0.5946(3) 1.1498(2) 0.6343(2) 0.038 Uiso 1 calc R . C19 C 0.6146(2) 1.0940(2) 0.4774(2) 0.0261(4) Uani 1 d . . H19 H 0.6710(2) 1.1474(2) 0.4532(2) 0.031 Uiso 1 calc R . C20 C 0.4431(2) 0.90500(14) 0.19533(14) 0.0166(4) Uani 1 d . . C21 C 0.4028(2) 0.80457(15) 0.1812(2) 0.0216(4) Uani 1 d . . H21 H 0.4690(2) 0.75218(15) 0.1830(2) 0.026 Uiso 1 calc R . C22 C 0.2667(2) 0.7801(2) 0.1647(2) 0.0267(4) Uani 1 d . . H22 H 0.2405(2) 0.7111(2) 0.1558(2) 0.032 Uiso 1 calc R . C23 C 0.1687(2) 0.8553(2) 0.1610(2) 0.0246(4) Uani 1 d . . H23 H 0.0756(2) 0.8382(2) 0.1495(2) 0.029 Uiso 1 calc R . C24 C 0.2079(2) 0.9553(2) 0.1743(2) 0.0247(4) Uani 1 d . . H24 H 0.1415(2) 1.0075(2) 0.1715(2) 0.030 Uiso 1 calc R . C25 C 0.3438(2) 0.9797(2) 0.1917(2) 0.0234(4) Uani 1 d . . H25 H 0.3695(2) 1.0488(2) 0.2013(2) 0.028 Uiso 1 calc R . C26 C 0.6455(2) 0.94295(14) 0.08824(14) 0.0166(4) Uani 1 d . . C27 C 0.7513(2) 0.88538(15) 0.0499(2) 0.0203(4) Uani 1 d . . H27 H 0.7939(2) 0.83610(15) 0.0976(2) 0.024 Uiso 1 calc R . C28 C 0.7959(2) 0.8990(2) -0.0579(2) 0.0262(4) Uani 1 d . . H28 H 0.8692(2) 0.8596(2) -0.0829(2) 0.031 Uiso 1 calc R . C29 C 0.7338(2) 0.9696(2) -0.1285(2) 0.0247(4) Uani 1 d . . H29 H 0.7637(2) 0.9787(2) -0.2022(2) 0.030 Uiso 1 calc R . C30 C 0.6274(2) 1.02704(15) -0.0907(2) 0.0223(4) Uani 1 d . . H30 H 0.5845(2) 1.07597(15) -0.1387(2) 0.027 Uiso 1 calc R . C31 C 0.5832(2) 1.01376(14) 0.01602(15) 0.0195(4) Uani 1 d . . H31 H 0.5096(2) 1.05319(14) 0.04061(15) 0.023 Uiso 1 calc R . C32 C 0.8386(2) 0.63221(14) 0.2710(2) 0.0192(4) Uani 1 d . . H32 H 0.7434(2) 0.64769(14) 0.2910(2) 0.023 Uiso 1 calc R . C33 C 0.8650(2) 0.52052(15) 0.3021(2) 0.0291(5) Uani 1 d . . H331 H 0.8471(2) 0.50997(15) 0.3812(2) 0.035 Uiso 1 calc R . H332 H 0.9598(2) 0.50354(15) 0.2893(2) 0.035 Uiso 1 calc R . H333 H 0.8050(2) 0.47680(15) 0.2557(2) 0.035 Uiso 1 calc R . N N 0.8473(2) 0.65471(12) 0.15058(13) 0.0214(3) Uani 1 d . . C34 C 0.7267(2) 0.6230(2) 0.0859(2) 0.0285(5) Uani 1 d . . H341 H 0.6468(2) 0.6562(2) 0.1152(2) 0.034 Uiso 1 calc R . H342 H 0.7166(2) 0.5491(2) 0.0914(2) 0.034 Uiso 1 calc R . H343 H 0.7352(2) 0.6421(2) 0.0074(2) 0.034 Uiso 1 calc R . C35 C 0.9677(2) 0.6142(2) 0.1016(2) 0.0343(5) Uani 1 d . . H351 H 1.0480(2) 0.6328(2) 0.1483(2) 0.041 Uiso 1 calc R . H352 H 0.9757(2) 0.6424(2) 0.0263(2) 0.041 Uiso 1 calc R . H353 H 0.9609(2) 0.5401(2) 0.0970(2) 0.041 Uiso 1 calc R . C36 C 0.7932(2) 0.6477(2) 0.5806(2) 0.0320(5) Uani 1 d . . H36 H 0.7590(2) 0.5812(2) 0.5505(2) 0.038 Uiso 1 calc R . C37 C 0.7292(2) 0.7423(2) 0.5646(2) 0.0351(5) Uani 1 d . . H37 H 0.6413(2) 0.7546(2) 0.5218(2) 0.042 Uiso 1 calc R . C38 C 0.8109(3) 0.8172(2) 0.6191(2) 0.0388(6) Uani 1 d . . H38 H 0.7905(3) 0.8915(2) 0.6223(2) 0.047 Uiso 1 calc R . C39 C 0.9258(3) 0.7682(2) 0.6691(2) 0.0387(6) Uani 1 d . . H39 H 1.0013(3) 0.8018(2) 0.7136(2) 0.046 Uiso 1 calc R . C40 C 0.9155(3) 0.6630(2) 0.6443(2) 0.0334(5) Uani 1 d . . H40 H 0.9824(3) 0.6094(2) 0.6682(2) 0.040 Uiso 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 Fe 0.02151(13) 0.01765(12) 0.01959(12) 0.00164(12) -0.00510(9) 0.00051(13) C1 0.0182(10) 0.0154(9) 0.0195(9) -0.0002(7) -0.0014(7) -0.0011(8) C2 0.0215(10) 0.0194(9) 0.0230(9) -0.0005(7) -0.0034(8) -0.0011(8) C3 0.0188(10) 0.0267(11) 0.0326(11) 0.0006(8) -0.0079(8) 0.0005(8) C4 0.0189(10) 0.0225(10) 0.0293(10) -0.0001(8) -0.0054(8) 0.0053(8) C5 0.0164(9) 0.0168(9) 0.0213(9) 0.0008(7) -0.0013(7) 0.0007(7) B 0.0177(10) 0.0169(10) 0.0148(9) 0.0006(7) -0.0016(7) -0.0017(8) O1 0.0162(7) 0.0128(6) 0.0186(6) 0.0012(5) -0.0031(5) 0.0021(5) O2 0.0155(7) 0.0142(6) 0.0225(7) -0.0002(5) -0.0048(5) 0.0008(5) C6 0.0177(9) 0.0107(8) 0.0176(8) -0.0003(6) -0.0032(6) 0.0007(7) C7 0.0166(9) 0.0146(8) 0.0187(9) -0.0030(6) -0.0032(7) 0.0013(7) C8 0.0235(10) 0.0137(8) 0.0174(8) -0.0023(6) -0.0055(7) -0.0001(7) C9 0.0271(11) 0.0186(10) 0.0254(10) -0.0048(8) -0.0062(8) 0.0022(8) C10 0.0376(13) 0.0156(9) 0.0343(12) -0.0019(8) -0.0114(10) 0.0070(8) C11 0.0482(15) 0.0173(10) 0.0312(11) 0.0033(8) -0.0120(10) -0.0034(10) C12 0.0348(11) 0.0241(10) 0.0250(9) 0.0015(9) -0.0041(7) -0.0085(11) C13 0.0224(10) 0.0179(9) 0.0230(9) -0.0019(7) -0.0053(7) -0.0018(8) C14 0.0173(9) 0.0180(9) 0.0167(9) -0.0023(6) -0.0045(7) 0.0050(7) C15 0.0227(10) 0.0240(10) 0.0181(9) -0.0019(7) -0.0036(7) 0.0022(8) C16 0.0228(10) 0.0316(11) 0.0195(10) 0.0019(8) -0.0016(8) 0.0005(9) C17 0.0249(11) 0.0414(13) 0.0179(10) -0.0025(8) -0.0023(8) 0.0069(10) C18 0.0378(13) 0.0330(12) 0.0225(10) -0.0110(9) -0.0058(9) 0.0026(10) C19 0.0308(12) 0.0259(11) 0.0214(10) -0.0055(8) -0.0025(8) -0.0030(9) C20 0.0178(9) 0.0188(9) 0.0131(8) 0.0004(6) -0.0007(6) 0.0005(7) C21 0.0175(10) 0.0194(9) 0.0277(10) -0.0013(7) 0.0002(7) 0.0012(8) C22 0.0198(10) 0.0235(10) 0.0367(11) -0.0033(8) -0.0002(8) -0.0044(8) C23 0.0142(9) 0.0353(11) 0.0240(10) -0.0015(8) -0.0007(7) -0.0013(8) C24 0.0182(10) 0.0282(11) 0.0273(10) -0.0019(8) -0.0022(7) 0.0056(8) C25 0.0202(10) 0.0196(9) 0.0299(10) -0.0034(8) -0.0038(8) 0.0023(8) C26 0.0169(9) 0.0164(8) 0.0163(8) -0.0016(6) -0.0025(6) -0.0043(7) C27 0.0198(10) 0.0204(9) 0.0208(9) -0.0007(7) -0.0002(7) 0.0000(8) C28 0.0254(11) 0.0255(10) 0.0280(10) -0.0044(8) 0.0058(8) -0.0007(9) C29 0.0293(11) 0.0267(10) 0.0184(9) -0.0010(7) 0.0034(7) -0.0087(9) C30 0.0276(11) 0.0196(9) 0.0191(9) 0.0019(7) -0.0049(8) -0.0058(8) C31 0.0222(10) 0.0171(9) 0.0189(9) -0.0025(7) -0.0029(7) -0.0010(8) C32 0.0173(9) 0.0157(9) 0.0244(9) -0.0009(7) -0.0022(7) 0.0010(7) C33 0.0316(12) 0.0173(10) 0.0376(12) 0.0019(8) -0.0069(9) 0.0005(9) N 0.0207(9) 0.0207(8) 0.0226(8) -0.0043(6) -0.0019(6) -0.0010(7) C34 0.0283(12) 0.0262(11) 0.0300(11) -0.0054(9) -0.0083(9) -0.0003(9) C35 0.0265(12) 0.0387(13) 0.0382(12) -0.0131(10) 0.0088(9) -0.0056(10) C36 0.0352(13) 0.0335(12) 0.0274(11) 0.0038(9) 0.0025(9) -0.0091(10) C37 0.0307(11) 0.0488(13) 0.0263(9) 0.0087(12) 0.0067(8) 0.0046(13) C38 0.059(2) 0.0298(12) 0.0283(12) -0.0019(10) 0.0148(11) 0.0042(12) C39 0.056(2) 0.041(2) 0.0185(9) 0.0000(9) -0.0050(9) -0.0134(12) C40 0.0416(14) 0.0321(12) 0.0259(11) 0.0109(9) -0.0049(9) -0.0006(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 Fe C38 2.030(2) . ? Fe C39 2.036(2) . ? Fe C2 2.037(2) . ? Fe C1 2.040(2) . ? Fe C40 2.041(2) . ? Fe C37 2.041(2) . ? Fe C5 2.041(2) . ? Fe C3 2.048(2) . ? Fe C36 2.051(2) . ? Fe C4 2.052(2) . ? C1 C2 1.433(3) . ? C1 C5 1.443(3) . ? C1 B 1.531(3) . ? C2 C3 1.410(3) . ? C3 C4 1.421(3) . ? C4 C5 1.431(3) . ? C5 C32 1.509(3) . ? B O1 1.376(2) . ? B O2 1.378(2) . ? O1 C6 1.450(2) . ? O2 C7 1.455(2) . ? C6 C20 1.519(3) . ? C6 C26 1.538(3) . ? C6 C7 1.594(2) . ? C7 C8 1.521(3) . ? C7 C14 1.533(3) . ? C8 C13 1.390(3) . ? C8 C9 1.393(3) . ? C9 C10 1.394(3) . ? C10 C11 1.378(4) . ? C11 C12 1.388(3) . ? C12 C13 1.386(3) . ? C14 C15 1.384(3) . ? C14 C19 1.397(3) . ? C15 C16 1.393(3) . ? C16 C17 1.375(3) . ? C17 C18 1.382(3) . ? C18 C19 1.386(3) . ? C20 C25 1.387(3) . ? C20 C21 1.389(3) . ? C21 C22 1.386(3) . ? C22 C23 1.382(3) . ? C23 C24 1.380(3) . ? C24 C25 1.386(3) . ? C26 C27 1.385(3) . ? C26 C31 1.396(3) . ? C27 C28 1.393(3) . ? C28 C29 1.381(3) . ? C29 C30 1.386(3) . ? C30 C31 1.379(3) . ? C32 N 1.478(2) . ? C32 C33 1.536(3) . ? N C35 1.450(3) . ? N C34 1.452(3) . ? C36 C37 1.406(4) . ? C36 C40 1.413(3) . ? C37 C38 1.415(4) . ? C38 C39 1.414(4) . ? C39 C40 1.419(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 C38 Fe C39 40.70(11) . . ? C38 Fe C2 108.23(10) . . ? C39 Fe C2 114.27(9) . . ? C38 Fe C1 115.09(9) . . ? C39 Fe C1 146.49(9) . . ? C2 Fe C1 41.16(8) . . ? C38 Fe C40 68.52(10) . . ? C39 Fe C40 40.75(10) . . ? C2 Fe C40 146.09(9) . . ? C1 Fe C40 171.90(9) . . ? C38 Fe C37 40.67(11) . . ? C39 Fe C37 68.24(10) . . ? C2 Fe C37 132.43(10) . . ? C1 Fe C37 109.46(9) . . ? C40 Fe C37 68.12(10) . . ? C38 Fe C5 147.92(10) . . ? C39 Fe C5 170.72(9) . . ? C2 Fe C5 69.11(8) . . ? C1 Fe C5 41.41(8) . . ? C40 Fe C5 131.94(9) . . ? C37 Fe C5 116.50(9) . . ? C38 Fe C3 130.91(10) . . ? C39 Fe C3 107.79(10) . . ? C2 Fe C3 40.37(8) . . ? C1 Fe C3 68.80(8) . . ? C40 Fe C3 114.90(9) . . ? C37 Fe C3 170.61(11) . . ? C5 Fe C3 68.74(9) . . ? C38 Fe C36 68.05(11) . . ? C39 Fe C36 68.04(10) . . ? C2 Fe C36 171.89(9) . . ? C1 Fe C36 132.92(9) . . ? C40 Fe C36 40.41(9) . . ? C37 Fe C36 40.18(11) . . ? C5 Fe C36 109.91(9) . . ? C3 Fe C36 147.45(9) . . ? C38 Fe C4 169.96(10) . . ? C39 Fe C4 131.04(10) . . ? C2 Fe C4 68.39(9) . . ? C1 Fe C4 69.07(8) . . ? C40 Fe C4 108.65(10) . . ? C37 Fe C4 148.32(10) . . ? C5 Fe C4 40.92(8) . . ? C3 Fe C4 40.58(8) . . ? C36 Fe C4 116.52(10) . . ? C2 C1 C5 107.1(2) . . ? C2 C1 B 122.9(2) . . ? C5 C1 B 129.7(2) . . ? C2 C1 Fe 69.31(11) . . ? C5 C1 Fe 69.35(12) . . ? B C1 Fe 122.20(14) . . ? C3 C2 C1 108.7(2) . . ? C3 C2 Fe 70.23(12) . . ? C1 C2 Fe 69.53(11) . . ? C2 C3 C4 108.5(2) . . ? C2 C3 Fe 69.40(12) . . ? C4 C3 Fe 69.85(12) . . ? C3 C4 C5 108.1(2) . . ? C3 C4 Fe 69.57(13) . . ? C5 C4 Fe 69.16(12) . . ? C4 C5 C1 107.6(2) . . ? C4 C5 C32 127.8(2) . . ? C1 C5 C32 124.5(2) . . ? C4 C5 Fe 69.93(12) . . ? C1 C5 Fe 69.24(12) . . ? C32 C5 Fe 127.71(15) . . ? O1 B O2 112.3(2) . . ? O1 B C1 127.0(2) . . ? O2 B C1 120.7(2) . . ? B O1 C6 106.70(14) . . ? B O2 C7 107.16(14) . . ? O1 C6 C20 109.03(14) . . ? O1 C6 C26 107.44(14) . . ? C20 C6 C26 107.92(14) . . ? O1 C6 C7 100.85(12) . . ? C20 C6 C7 118.8(2) . . ? C26 C6 C7 112.10(15) . . ? O2 C7 C8 108.19(15) . . ? O2 C7 C14 104.41(14) . . ? C8 C7 C14 113.31(15) . . ? O2 C7 C6 100.04(13) . . ? C8 C7 C6 114.32(14) . . ? C14 C7 C6 114.9(2) . . ? C13 C8 C9 118.6(2) . . ? C13 C8 C7 120.2(2) . . ? C9 C8 C7 121.1(2) . . ? C8 C9 C10 120.4(2) . . ? C11 C10 C9 120.1(2) . . ? C10 C11 C12 119.9(2) . . ? C13 C12 C11 119.9(2) . . ? C12 C13 C8 120.9(2) . . ? C15 C14 C19 117.9(2) . . ? C15 C14 C7 124.7(2) . . ? C19 C14 C7 117.0(2) . . ? C14 C15 C16 120.9(2) . . ? C17 C16 C15 120.5(2) . . ? C16 C17 C18 119.4(2) . . ? C17 C18 C19 120.1(2) . . ? C18 C19 C14 121.1(2) . . ? C25 C20 C21 118.3(2) . . ? C25 C20 C6 123.5(2) . . ? C21 C20 C6 118.2(2) . . ? C22 C21 C20 120.6(2) . . ? C23 C22 C21 120.7(2) . . ? C24 C23 C22 119.2(2) . . ? C23 C24 C25 120.2(2) . . ? C24 C25 C20 121.1(2) . . ? C27 C26 C31 118.6(2) . . ? C27 C26 C6 121.2(2) . . ? C31 C26 C6 120.2(2) . . ? C26 C27 C28 120.7(2) . . ? C29 C28 C27 120.3(2) . . ? C28 C29 C30 119.3(2) . . ? C31 C30 C29 120.6(2) . . ? C30 C31 C26 120.6(2) . . ? N C32 C5 108.9(2) . . ? N C32 C33 114.3(2) . . ? C5 C32 C33 112.9(2) . . ? C35 N C34 110.2(2) . . ? C35 N C32 113.9(2) . . ? C34 N C32 112.3(2) . . ? C37 C36 C40 108.4(2) . . ? C37 C36 Fe 69.52(13) . . ? C40 C36 Fe 69.39(13) . . ? C36 C37 C38 108.1(2) . . ? C36 C37 Fe 70.30(13) . . ? C38 C37 Fe 69.27(14) . . ? C39 C38 C37 107.9(2) . . ? C39 C38 Fe 69.84(14) . . ? C37 C38 Fe 70.06(13) . . ? C38 C39 C40 108.0(2) . . ? C38 C39 Fe 69.46(13) . . ? C40 C39 Fe 69.81(13) . . ? C36 C40 C39 107.7(2) . . ? C36 C40 Fe 70.20(13) . . ? C39 C40 Fe 69.44(13) . . ? _refine_diff_density_max 0.217 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.044 #===END data_B102377M-4a _database_code_CSD 160673 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H18 B Fe N O2' _chemical_formula_weight 286.94 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 '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 ? _symmetry_space_group_name_H-M ? 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 12.452(3) _cell_length_b 12.858(3) _cell_length_c 17.078(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.77(3) _cell_angle_gamma 90.00 _cell_volume 2643.9(9) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method ? _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.132 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17656 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 29.68 _reflns_number_total 6747 _reflns_number_observed 5865 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.8038P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6747 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_obs 0.0231 _refine_ls_wR_factor_all 0.0653 _refine_ls_wR_factor_obs 0.0631 _refine_ls_goodness_of_fit_all 1.051 _refine_ls_goodness_of_fit_obs 1.093 _refine_ls_restrained_S_all 1.051 _refine_ls_restrained_S_obs 1.093 _refine_ls_shift/esd_max 0.003 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Fe1 Fe 0.646853(13) 0.822532(13) 0.149113(10) 0.01684(5) Uani 1 d . . O1 O 0.92994(7) 0.69303(7) 0.29395(5) 0.0200(2) Uani 1 d . . H1O H 0.90662(7) 0.72555(7) 0.32898(5) 0.024 Uiso 1 calc R . O2 O 0.85739(7) 0.60887(7) 0.16779(5) 0.0224(2) Uani 1 d . . H2O H 0.92431(7) 0.59085(7) 0.17723(5) 0.027 Uiso 1 calc R . B1 B 0.84239(11) 0.66887(10) 0.22980(8) 0.0170(2) Uani 1 d . . C1 C 0.72291(10) 0.70869(9) 0.22698(7) 0.0175(2) Uani 1 d . . C2 C 0.62184(10) 0.67024(10) 0.17396(8) 0.0215(2) Uani 1 d . . H2 H 0.61617(10) 0.61095(10) 0.13521(8) 0.026 Uiso 1 calc R . C3 C 0.53116(11) 0.73186(11) 0.18446(9) 0.0260(3) Uani 1 d . . H3 H 0.45147(11) 0.72337(11) 0.15444(9) 0.031 Uiso 1 calc R . C4 C 0.57449(11) 0.80876(11) 0.24410(8) 0.0244(3) Uani 1 d . . H4 H 0.53033(11) 0.86374(11) 0.26320(8) 0.029 Uiso 1 calc R . C5 C 0.69250(10) 0.79577(10) 0.27048(7) 0.0189(2) Uani 1 d . . C6 C 0.77136(11) 0.86456(10) 0.32976(7) 0.0208(2) Uani 1 d . . H61 H 0.81665(11) 0.90512(10) 0.30064(7) 0.025 Uiso 1 calc R . H62 H 0.72822(11) 0.91431(10) 0.35386(7) 0.025 Uiso 1 calc R . N1 N 0.84576(9) 0.80395(8) 0.39506(6) 0.0207(2) Uani 1 d . . C7 C 0.92882(12) 0.87259(11) 0.44647(8) 0.0278(3) Uani 1 d . . H71 H 0.97239(12) 0.90666(11) 0.41344(8) 0.033 Uiso 1 calc R . H72 H 0.97830(12) 0.83146(11) 0.48909(8) 0.033 Uiso 1 calc R . H73 H 0.89122(12) 0.92545(11) 0.47119(8) 0.033 Uiso 1 calc R . C8 C 0.78282(13) 0.74722(12) 0.44324(8) 0.0295(3) Uani 1 d . . H81 H 0.73038(13) 0.69973(12) 0.40803(8) 0.035 Uiso 1 calc R . H82 H 0.74186(13) 0.79677(12) 0.46828(8) 0.035 Uiso 1 calc R . H83 H 0.83419(13) 0.70724(12) 0.48559(8) 0.035 Uiso 1 calc R . C9 C 0.60320(12) 0.96504(10) 0.09731(9) 0.0286(3) Uani 1 d . . H9 H 0.54899(12) 1.01466(10) 0.11115(9) 0.034 Uiso 1 calc R . C10 C 0.71925(12) 0.96121(10) 0.13396(8) 0.0243(3) Uani 1 d . . H10 H 0.76097(12) 1.00768(10) 0.17831(8) 0.029 Uiso 1 calc R . C11 C 0.76577(12) 0.87902(11) 0.09705(8) 0.0261(3) Uani 1 d . . H11 H 0.84569(12) 0.85790(11) 0.11068(8) 0.031 Uiso 1 calc R . C12 C 0.67786(14) 0.83253(11) 0.03725(8) 0.0307(3) Uani 1 d . . H12 H 0.68520(14) 0.77257(11) 0.00169(8) 0.037 Uiso 1 calc R . C13 C 0.57800(13) 0.88547(12) 0.03729(9) 0.0322(3) Uani 1 d . . H13 H 0.50270(13) 0.86918(12) 0.00184(9) 0.039 Uiso 1 calc R . Fe2 Fe 0.142255(13) 0.929233(13) 0.160781(10) 0.01483(5) Uani 1 d . . O3 O 0.42877(7) 1.04182(7) 0.30997(5) 0.0203(2) Uani 1 d . . H3O H 0.40489(7) 1.01283(7) 0.34626(5) 0.024 Uiso 1 calc R . O4 O 0.35612(7) 1.13616(7) 0.18850(6) 0.0241(2) Uani 1 d . . H4O H 0.42381(7) 1.15111(7) 0.19718(6) 0.029 Uiso 1 calc R . B2 B 0.34070(11) 1.07253(10) 0.24794(8) 0.0176(2) Uani 1 d . . C14 C 0.21992(10) 1.03613(9) 0.24454(7) 0.0167(2) Uani 1 d . . C15 C 0.12086(10) 1.07926(10) 0.19218(8) 0.0205(2) Uani 1 d . . H15 H 0.11786(10) 1.14126(10) 0.15634(8) 0.025 Uiso 1 calc R . C16 C 0.02798(10) 1.01834(11) 0.19846(8) 0.0243(3) Uani 1 d . . H16 H -0.05100(10) 1.03001(11) 0.16792(8) 0.029 Uiso 1 calc R . C17 C 0.06756(10) 0.93682(10) 0.25494(8) 0.0225(2) Uani 1 d . . H17 H 0.02112(10) 0.88113(10) 0.27078(8) 0.027 Uiso 1 calc R . C18 C 0.18561(10) 0.94677(9) 0.28351(7) 0.0177(2) Uani 1 d . . C19 C 0.26142(11) 0.87388(10) 0.34152(7) 0.0221(2) Uani 1 d . . H191 H 0.21595(11) 0.82491(10) 0.36426(7) 0.026 Uiso 1 calc R . H192 H 0.30517(11) 0.83268(10) 0.31162(7) 0.026 Uiso 1 calc R . N2 N 0.33811(9) 0.92998(8) 0.40847(6) 0.0201(2) Uani 1 d . . C20 C 0.27771(13) 0.98632(12) 0.45816(8) 0.0307(3) Uani 1 d . . H201 H 0.22572(13) 1.03521(12) 0.42411(8) 0.037 Uiso 1 calc R . H202 H 0.33049(13) 1.02473(12) 0.50071(8) 0.037 Uiso 1 calc R . H203 H 0.23642(13) 0.93680(12) 0.48296(8) 0.037 Uiso 1 calc R . C21 C 0.41666(12) 0.85678(12) 0.45851(8) 0.0290(3) Uani 1 d . . H211 H 0.45957(12) 0.82234(12) 0.42520(8) 0.035 Uiso 1 calc R . H212 H 0.37572(12) 0.80449(12) 0.48107(8) 0.035 Uiso 1 calc R . H213 H 0.46722(12) 0.89456(12) 0.50275(8) 0.035 Uiso 1 calc R . C22 C 0.09875(12) 0.79128(10) 0.10090(8) 0.0238(3) Uani 1 d . . H22 H 0.04453(12) 0.73949(10) 0.11195(8) 0.029 Uiso 1 calc R . C23 C 0.21492(11) 0.79370(10) 0.13827(8) 0.0224(2) Uani 1 d . . H23 H 0.25652(11) 0.74374(10) 0.17997(8) 0.027 Uiso 1 calc R . C24 C 0.26138(11) 0.88059(10) 0.10637(8) 0.0242(3) Uani 1 d . . H24 H 0.34124(11) 0.90196(10) 0.12144(8) 0.029 Uiso 1 calc R . C25 C 0.17346(13) 0.93124(11) 0.04891(8) 0.0269(3) Uani 1 d . . H25 H 0.18091(13) 0.99480(11) 0.01695(8) 0.032 Uiso 1 calc R . C26 C 0.07314(12) 0.87620(11) 0.04552(8) 0.0265(3) Uani 1 d . . H26 H -0.00216(12) 0.89444(11) 0.01098(8) 0.032 Uiso 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 0.01552(8) 0.01434(9) 0.02005(9) 0.00401(6) 0.00342(6) 0.00231(6) O1 0.0164(4) 0.0231(4) 0.0205(4) -0.0030(3) 0.0050(3) 0.0045(3) O2 0.0177(4) 0.0230(4) 0.0249(4) -0.0055(4) 0.0026(3) 0.0043(3) B1 0.0173(6) 0.0136(6) 0.0208(6) 0.0031(5) 0.0059(5) 0.0021(5) C1 0.0167(5) 0.0151(5) 0.0210(5) 0.0049(4) 0.0054(4) 0.0026(4) C2 0.0186(5) 0.0161(6) 0.0293(6) 0.0055(5) 0.0053(5) -0.0003(4) C3 0.0159(5) 0.0259(6) 0.0369(7) 0.0078(5) 0.0080(5) 0.0002(5) C4 0.0198(6) 0.0257(6) 0.0310(7) 0.0071(5) 0.0125(5) 0.0055(5) C5 0.0201(5) 0.0182(5) 0.0202(5) 0.0061(4) 0.0083(4) 0.0053(4) C6 0.0253(6) 0.0180(6) 0.0195(5) 0.0027(4) 0.0066(5) 0.0060(5) N1 0.0254(5) 0.0218(5) 0.0159(5) 0.0031(4) 0.0073(4) 0.0055(4) C7 0.0305(7) 0.0310(7) 0.0209(6) -0.0020(5) 0.0050(5) 0.0042(6) C8 0.0379(8) 0.0317(7) 0.0233(6) 0.0078(5) 0.0158(6) 0.0053(6) C9 0.0328(7) 0.0177(6) 0.0326(7) 0.0093(5) 0.0034(6) 0.0057(5) C10 0.0321(7) 0.0169(6) 0.0236(6) 0.0052(5) 0.0065(5) -0.0031(5) C11 0.0296(7) 0.0254(7) 0.0264(6) 0.0069(5) 0.0129(5) -0.0011(5) C12 0.0482(9) 0.0240(7) 0.0204(6) 0.0025(5) 0.0100(6) -0.0019(6) C13 0.0378(8) 0.0262(7) 0.0253(7) 0.0091(5) -0.0055(6) -0.0015(6) Fe2 0.01525(8) 0.01317(8) 0.01637(8) -0.00101(6) 0.00460(6) -0.00145(6) O3 0.0159(4) 0.0221(4) 0.0225(4) 0.0047(3) 0.0040(3) -0.0030(3) O4 0.0173(4) 0.0228(5) 0.0300(5) 0.0085(4) 0.0021(3) -0.0046(3) B2 0.0164(6) 0.0135(6) 0.0225(6) -0.0014(5) 0.0043(5) -0.0012(5) C14 0.0165(5) 0.0133(5) 0.0202(5) -0.0029(4) 0.0045(4) -0.0010(4) C15 0.0176(5) 0.0156(5) 0.0276(6) -0.0037(4) 0.0045(5) 0.0015(4) C16 0.0153(5) 0.0255(6) 0.0324(7) -0.0070(5) 0.0066(5) 0.0005(5) C17 0.0198(6) 0.0261(6) 0.0247(6) -0.0061(5) 0.0114(5) -0.0059(5) C18 0.0197(5) 0.0176(5) 0.0170(5) -0.0039(4) 0.0072(4) -0.0041(4) C19 0.0293(6) 0.0171(6) 0.0186(5) -0.0006(4) 0.0038(5) -0.0043(5) N2 0.0238(5) 0.0194(5) 0.0166(5) -0.0010(4) 0.0043(4) -0.0018(4) C20 0.0370(8) 0.0358(8) 0.0208(6) -0.0061(5) 0.0100(5) 0.0016(6) C21 0.0315(7) 0.0276(7) 0.0246(6) 0.0054(5) 0.0014(5) -0.0008(6) C22 0.0319(7) 0.0168(6) 0.0217(6) -0.0048(5) 0.0048(5) -0.0045(5) C23 0.0304(6) 0.0172(6) 0.0198(6) -0.0021(4) 0.0069(5) 0.0046(5) C24 0.0271(6) 0.0238(6) 0.0255(6) -0.0040(5) 0.0139(5) 0.0022(5) C25 0.0416(8) 0.0223(6) 0.0203(6) 0.0019(5) 0.0144(5) 0.0021(6) C26 0.0341(7) 0.0244(7) 0.0179(6) -0.0022(5) 0.0007(5) 0.0025(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 C5 2.0340(13) . ? Fe1 C1 2.0410(12) . ? Fe1 C10 2.0440(13) . ? Fe1 C2 2.0443(13) . ? Fe1 C11 2.0450(14) . ? Fe1 C9 2.0471(13) . ? Fe1 C12 2.0472(14) . ? Fe1 C13 2.0499(14) . ? Fe1 C4 2.0543(14) . ? Fe1 C3 2.0597(13) . ? O1 B1 1.370(2) . ? O2 B1 1.361(2) . ? B1 C1 1.562(2) . ? C1 C2 1.438(2) . ? C1 C5 1.447(2) . ? C2 C3 1.428(2) . ? C3 C4 1.423(2) . ? C4 C5 1.433(2) . ? C5 C6 1.505(2) . ? C6 N1 1.477(2) . ? N1 C8 1.467(2) . ? N1 C7 1.468(2) . ? C9 C10 1.422(2) . ? C9 C13 1.426(2) . ? C10 C11 1.427(2) . ? C11 C12 1.424(2) . ? C12 C13 1.418(2) . ? Fe2 C15 2.0378(13) . ? Fe2 C24 2.0391(13) . ? Fe2 C18 2.0391(13) . ? Fe2 C14 2.0409(12) . ? Fe2 C23 2.0446(13) . ? Fe2 C25 2.0447(13) . ? Fe2 C22 2.0501(13) . ? Fe2 C26 2.0535(14) . ? Fe2 C16 2.0539(13) . ? Fe2 C17 2.0550(13) . ? O3 B2 1.374(2) . ? O4 B2 1.355(2) . ? B2 C14 1.562(2) . ? C14 C15 1.437(2) . ? C14 C18 1.446(2) . ? C15 C16 1.423(2) . ? C16 C17 1.425(2) . ? C17 C18 1.432(2) . ? C18 C19 1.508(2) . ? C19 N2 1.477(2) . ? N2 C20 1.461(2) . ? N2 C21 1.465(2) . ? C22 C23 1.425(2) . ? C22 C26 1.426(2) . ? C23 C24 1.428(2) . ? C24 C25 1.427(2) . ? C25 C26 1.424(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Fe1 C1 41.59(5) . . ? C5 Fe1 C10 105.01(5) . . ? C1 Fe1 C10 124.18(5) . . ? C5 Fe1 C2 69.16(5) . . ? C1 Fe1 C2 41.21(5) . . ? C10 Fe1 C2 163.21(5) . . ? C5 Fe1 C11 117.26(6) . . ? C1 Fe1 C11 105.71(5) . . ? C10 Fe1 C11 40.85(5) . . ? C2 Fe1 C11 126.58(5) . . ? C5 Fe1 C9 124.49(6) . . ? C1 Fe1 C9 162.08(6) . . ? C10 Fe1 C9 40.67(6) . . ? C2 Fe1 C9 155.43(6) . . ? C11 Fe1 C9 68.66(6) . . ? C5 Fe1 C12 153.05(6) . . ? C1 Fe1 C12 119.11(6) . . ? C10 Fe1 C12 68.46(6) . . ? C2 Fe1 C12 109.20(6) . . ? C11 Fe1 C12 40.73(6) . . ? C9 Fe1 C12 68.47(6) . . ? C5 Fe1 C13 163.34(6) . . ? C1 Fe1 C13 154.75(6) . . ? C10 Fe1 C13 68.34(6) . . ? C2 Fe1 C13 121.46(6) . . ? C11 Fe1 C13 68.41(6) . . ? C9 Fe1 C13 40.72(6) . . ? C12 Fe1 C13 40.49(6) . . ? C5 Fe1 C4 41.02(5) . . ? C1 Fe1 C4 69.38(5) . . ? C10 Fe1 C4 118.14(6) . . ? C2 Fe1 C4 68.46(5) . . ? C11 Fe1 C4 152.37(6) . . ? C9 Fe1 C4 107.27(6) . . ? C12 Fe1 C4 165.31(6) . . ? C13 Fe1 C4 127.32(6) . . ? C5 Fe1 C3 68.91(6) . . ? C1 Fe1 C3 69.27(5) . . ? C10 Fe1 C3 153.49(6) . . ? C2 Fe1 C3 40.71(5) . . ? C11 Fe1 C3 165.13(6) . . ? C9 Fe1 C3 120.32(6) . . ? C12 Fe1 C3 128.42(6) . . ? C13 Fe1 C3 109.81(6) . . ? C4 Fe1 C3 40.48(6) . . ? O2 B1 O1 120.79(11) . . ? O2 B1 C1 118.70(11) . . ? O1 B1 C1 120.51(11) . . ? C2 C1 C5 106.73(10) . . ? C2 C1 B1 125.48(11) . . ? C5 C1 B1 127.57(11) . . ? C2 C1 Fe1 69.52(7) . . ? C5 C1 Fe1 68.95(7) . . ? B1 C1 Fe1 122.35(8) . . ? C3 C2 C1 108.86(12) . . ? C3 C2 Fe1 70.23(7) . . ? C1 C2 Fe1 69.27(7) . . ? C4 C3 C2 107.93(11) . . ? C4 C3 Fe1 69.55(7) . . ? C2 C3 Fe1 69.06(7) . . ? C3 C4 C5 108.38(11) . . ? C3 C4 Fe1 69.97(7) . . ? C5 C4 Fe1 68.73(7) . . ? C4 C5 C1 108.09(11) . . ? C4 C5 C6 125.74(11) . . ? C1 C5 C6 126.09(11) . . ? C4 C5 Fe1 70.25(8) . . ? C1 C5 Fe1 69.47(7) . . ? C6 C5 Fe1 123.43(8) . . ? N1 C6 C5 111.95(10) . . ? C8 N1 C7 111.04(11) . . ? C8 N1 C6 111.34(10) . . ? C7 N1 C6 110.17(10) . . ? C10 C9 C13 107.72(13) . . ? C10 C9 Fe1 69.55(7) . . ? C13 C9 Fe1 69.74(8) . . ? C9 C10 C11 108.23(12) . . ? C9 C10 Fe1 69.78(7) . . ? C11 C10 Fe1 69.61(7) . . ? C12 C11 C10 107.65(13) . . ? C12 C11 Fe1 69.72(8) . . ? C10 C11 Fe1 69.54(7) . . ? C13 C12 C11 108.19(13) . . ? C13 C12 Fe1 69.86(8) . . ? C11 C12 Fe1 69.55(8) . . ? C12 C13 C9 108.21(13) . . ? C12 C13 Fe1 69.65(8) . . ? C9 C13 Fe1 69.53(8) . . ? C15 Fe2 C24 124.71(5) . . ? C15 Fe2 C18 69.08(5) . . ? C24 Fe2 C18 118.01(6) . . ? C15 Fe2 C14 41.27(5) . . ? C24 Fe2 C14 104.85(5) . . ? C18 Fe2 C14 41.51(5) . . ? C15 Fe2 C23 161.82(5) . . ? C24 Fe2 C23 40.95(5) . . ? C18 Fe2 C23 105.88(5) . . ? C14 Fe2 C23 123.54(5) . . ? C15 Fe2 C25 107.62(5) . . ? C24 Fe2 C25 40.92(6) . . ? C18 Fe2 C25 153.57(6) . . ? C14 Fe2 C25 118.52(5) . . ? C23 Fe2 C25 68.68(5) . . ? C15 Fe2 C22 156.16(5) . . ? C24 Fe2 C22 68.76(6) . . ? C18 Fe2 C22 125.13(5) . . ? C14 Fe2 C22 161.81(5) . . ? C23 Fe2 C22 40.72(5) . . ? C25 Fe2 C22 68.52(6) . . ? C15 Fe2 C26 121.04(5) . . ? C24 Fe2 C26 68.72(6) . . ? C18 Fe2 C26 163.42(5) . . ? C14 Fe2 C26 154.61(5) . . ? C23 Fe2 C26 68.54(6) . . ? C25 Fe2 C26 40.67(6) . . ? C22 Fe2 C26 40.68(5) . . ? C15 Fe2 C16 40.71(5) . . ? C24 Fe2 C16 163.03(6) . . ? C18 Fe2 C16 68.86(6) . . ? C14 Fe2 C16 69.33(5) . . ? C23 Fe2 C16 155.43(5) . . ? C25 Fe2 C16 126.70(6) . . ? C22 Fe2 C16 121.53(6) . . ? C26 Fe2 C16 109.34(6) . . ? C15 Fe2 C17 68.50(5) . . ? C24 Fe2 C17 153.92(6) . . ? C18 Fe2 C17 40.93(5) . . ? C14 Fe2 C17 69.37(5) . . ? C23 Fe2 C17 119.86(5) . . ? C25 Fe2 C17 164.23(6) . . ? C22 Fe2 C17 108.46(5) . . ? C26 Fe2 C17 127.10(6) . . ? C16 Fe2 C17 40.57(6) . . ? O4 B2 O3 120.89(11) . . ? O4 B2 C14 118.17(11) . . ? O3 B2 C14 120.94(11) . . ? C15 C14 C18 106.59(10) . . ? C15 C14 B2 124.95(11) . . ? C18 C14 B2 128.00(11) . . ? C15 C14 Fe2 69.25(7) . . ? C18 C14 Fe2 69.18(7) . . ? B2 C14 Fe2 120.50(8) . . ? C16 C15 C14 109.01(11) . . ? C16 C15 Fe2 70.25(7) . . ? C14 C15 Fe2 69.48(7) . . ? C15 C16 C17 107.96(11) . . ? C15 C16 Fe2 69.03(7) . . ? C17 C16 Fe2 69.76(7) . . ? C16 C17 C18 108.23(11) . . ? C16 C17 Fe2 69.67(7) . . ? C18 C17 Fe2 68.94(7) . . ? C17 C18 C14 108.20(11) . . ? C17 C18 C19 125.78(11) . . ? C14 C18 C19 125.98(11) . . ? C17 C18 Fe2 70.13(7) . . ? C14 C18 Fe2 69.31(7) . . ? C19 C18 Fe2 124.33(8) . . ? N2 C19 C18 112.20(10) . . ? C20 N2 C21 110.21(11) . . ? C20 N2 C19 111.38(11) . . ? C21 N2 C19 109.96(10) . . ? C23 C22 C26 108.07(12) . . ? C23 C22 Fe2 69.43(7) . . ? C26 C22 Fe2 69.79(8) . . ? C22 C23 C24 108.05(11) . . ? C22 C23 Fe2 69.85(7) . . ? C24 C23 Fe2 69.32(7) . . ? C25 C24 C23 107.75(12) . . ? C25 C24 Fe2 69.75(7) . . ? C23 C24 Fe2 69.73(7) . . ? C26 C25 C24 108.19(12) . . ? C26 C25 Fe2 70.00(8) . . ? C24 C25 Fe2 69.33(7) . . ? C25 C26 C22 107.94(12) . . ? C25 C26 Fe2 69.34(8) . . ? C22 C26 Fe2 69.53(7) . . ? _refine_diff_density_max 0.388 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.047 #===END data_B102377M-4b _database_code_CSD 160674 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H18 B Fe N O2' _chemical_formula_weight 286.94 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 21.431(4) _cell_length_b 6.1956(12) _cell_length_c 20.414(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2710.6(9) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method ? _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.104 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17557 _diffrn_reflns_av_R_equivalents 0.1247 _diffrn_reflns_av_sigmaI/netI 0.1783 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 29.71 _reflns_number_total 6844 _reflns_number_observed 3866 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0444P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.47(3) _refine_ls_number_reflns 6844 _refine_ls_number_parameters 325 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1632 _refine_ls_R_factor_obs 0.0788 _refine_ls_wR_factor_all 0.1533 _refine_ls_wR_factor_obs 0.1223 _refine_ls_goodness_of_fit_all 1.052 _refine_ls_goodness_of_fit_obs 1.133 _refine_ls_restrained_S_all 1.052 _refine_ls_restrained_S_obs 1.133 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Fe1 Fe 0.00730(4) 0.89065(15) 0.06182(4) 0.0179(2) Uani 1 d . . C1 C 0.0019(4) 1.0475(11) -0.0263(4) 0.017(2) Uani 1 d . . C2 C 0.0375(3) 1.1681(11) 0.0199(3) 0.017(2) Uani 1 d . . H2 H 0.0276(3) 1.3171(11) 0.0355(3) 0.020 Uiso 1 calc R . C3 C 0.0900(4) 1.0403(13) 0.0407(4) 0.021(2) Uani 1 d . . H3 H 0.1229(4) 1.0839(13) 0.0728(4) 0.025 Uiso 1 calc R . C4 C 0.0861(3) 0.8399(12) 0.0067(3) 0.020(2) Uani 1 d . . H4 H 0.1156(3) 0.7160(12) 0.0118(3) 0.024 Uiso 1 calc R . C5 C 0.0338(3) 0.8435(11) -0.0344(3) 0.018(2) Uani 1 d . . B1 B -0.0584(4) 1.1260(13) -0.0611(4) 0.020(2) Uani 1 d . . O1 O -0.0771(2) 1.0361(7) -0.1194(3) 0.0206(13) Uani 1 d . . H1O H -0.0478(2) 0.9624(7) -0.1351(3) 0.025 Uiso 1 calc R . O2 O -0.0947(2) 1.2832(7) -0.0333(2) 0.0229(12) Uani 1 d . . H2O H -0.1145(2) 1.3485(7) -0.0627(2) 0.028 Uiso 1 calc R . C6 C 0.0131(3) 0.6656(11) -0.0798(3) 0.018(2) Uani 1 d . . H61 H 0.0437(3) 0.5462(11) -0.0782(3) 0.022 Uiso 1 calc R . H62 H -0.0276(3) 0.6085(11) -0.0648(3) 0.022 Uiso 1 calc R . N1 N 0.0071(3) 0.7427(9) -0.1479(3) 0.0189(14) Uani 1 d . . C7 C -0.0156(5) 0.5692(13) -0.1907(3) 0.032(2) Uani 1 d . . H71 H -0.0527(5) 0.5032(13) -0.1713(3) 0.038 Uiso 1 calc R . H72 H 0.0171(5) 0.4595(13) -0.1957(3) 0.038 Uiso 1 calc R . H73 H -0.0261(5) 0.6290(13) -0.2337(3) 0.038 Uiso 1 calc R . C8 C 0.0662(4) 0.8279(13) -0.1729(4) 0.026(2) Uani 1 d . . H81 H 0.0819(4) 0.9394(13) -0.1431(4) 0.031 Uiso 1 calc R . H82 H 0.0596(4) 0.8908(13) -0.2164(4) 0.031 Uiso 1 calc R . H83 H 0.0968(4) 0.7107(13) -0.1760(4) 0.031 Uiso 1 calc R . C9 C -0.0550(4) 0.6553(14) 0.0884(4) 0.032(2) Uani 1 d . . H9 H -0.0712(4) 0.5381(14) 0.0593(4) 0.039 Uiso 1 calc R . C10 C -0.0012(4) 0.6426(12) 0.1284(4) 0.031(2) Uani 1 d . . H10 H 0.0272(4) 0.5154(12) 0.1326(4) 0.037 Uiso 1 calc R . C11 C 0.0061(4) 0.8483(13) 0.1606(4) 0.030(2) Uani 1 d . . H11 H 0.0403(4) 0.8882(13) 0.1917(4) 0.036 Uiso 1 calc R . C12 C -0.0444(4) 0.9858(13) 0.1404(5) 0.027(2) Uani 1 d . . H12 H -0.0519(4) 1.1377(13) 0.1550(5) 0.033 Uiso 1 calc R . C13 C -0.0815(4) 0.8659(14) 0.0953(4) 0.034(2) Uani 1 d . . H13 H -0.1196(4) 0.9200(14) 0.0723(4) 0.041 Uiso 1 calc R . Fe2 Fe 0.25465(5) 0.42847(15) 0.19422(5) 0.0180(2) Uani 1 d . . C14 C 0.2593(4) 0.5805(11) 0.2824(3) 0.015(2) Uani 1 d . . C15 C 0.2903(3) 0.7021(12) 0.2332(3) 0.021(2) Uani 1 d . . H15 H 0.2795(3) 0.8524(12) 0.2195(3) 0.025 Uiso 1 calc R . C16 C 0.3388(3) 0.5763(12) 0.2070(4) 0.022(2) Uani 1 d . . H16 H 0.3677(3) 0.6218(12) 0.1711(4) 0.026 Uiso 1 calc R . C17 C 0.3391(3) 0.3750(13) 0.2383(3) 0.019(2) Uani 1 d . . H17 H 0.3683(3) 0.2527(13) 0.2291(3) 0.023 Uiso 1 calc R . C18 C 0.2893(4) 0.3760(11) 0.2859(3) 0.017(2) Uani 1 d . . B2 B 0.1981(4) 0.6513(14) 0.3210(4) 0.021(2) Uani 1 d . . O3 O 0.1817(2) 0.5590(8) 0.3789(3) 0.0193(11) Uani 1 d . . H3O H 0.1992(2) 0.4382(8) 0.3824(3) 0.023 Uiso 1 calc R . O4 O 0.1629(2) 0.8132(7) 0.2946(2) 0.0217(11) Uani 1 d . . H4O H 0.1338(2) 0.8449(7) 0.3204(2) 0.026 Uiso 1 calc R . C19 C 0.2722(4) 0.1907(12) 0.3310(3) 0.021(2) Uani 1 d . . H191 H 0.2317(4) 0.1297(12) 0.3169(3) 0.026 Uiso 1 calc R . H192 H 0.3040(4) 0.0757(12) 0.3269(3) 0.026 Uiso 1 calc R . N2 N 0.2677(3) 0.2554(9) 0.3998(3) 0.0181(14) Uani 1 d . . C20 C 0.2472(4) 0.0708(10) 0.4386(4) 0.027(2) Uani 1 d . . H201 H 0.2338(4) 0.1204(10) 0.4820(4) 0.032 Uiso 1 calc R . H202 H 0.2818(4) -0.0314(10) 0.4434(4) 0.032 Uiso 1 calc R . H203 H 0.2122(4) -0.0006(10) 0.4165(4) 0.032 Uiso 1 calc R . C21 C 0.3272(3) 0.3408(12) 0.4236(3) 0.022(2) Uani 1 d . . H211 H 0.3384(3) 0.4694(12) 0.3983(3) 0.027 Uiso 1 calc R . H212 H 0.3597(3) 0.2310(12) 0.4185(3) 0.027 Uiso 1 calc R . H213 H 0.3232(3) 0.3792(12) 0.4700(3) 0.027 Uiso 1 calc R . C22 C 0.1924(5) 0.5204(15) 0.1252(5) 0.039(3) Uani 1 d . . H22 H 0.1817(5) 0.6733(15) 0.1142(5) 0.046 Uiso 1 calc R . C23 C 0.2404(4) 0.4005(14) 0.0961(4) 0.033(2) Uani 1 d . . H23 H 0.2692(4) 0.4507(14) 0.0606(4) 0.039 Uiso 1 calc R . C24 C 0.2399(4) 0.1904(12) 0.1261(3) 0.025(2) Uani 1 d . . H24 H 0.2686(4) 0.0678(12) 0.1158(3) 0.030 Uiso 1 calc R . C25 C 0.1919(3) 0.1902(12) 0.1728(3) 0.024(2) Uani 1 d . . H25 H 0.1803(3) 0.0669(12) 0.2019(3) 0.029 Uiso 1 calc R . C26 C 0.1628(4) 0.3982(14) 0.1719(4) 0.033(2) Uani 1 d . . H26 H 0.1270(4) 0.4453(14) 0.1999(4) 0.040 Uiso 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 0.0204(6) 0.0185(5) 0.0149(4) 0.0010(6) 0.0020(5) 0.0022(4) C1 0.010(4) 0.019(4) 0.021(4) 0.006(3) 0.003(3) -0.004(3) C2 0.012(4) 0.015(4) 0.023(4) -0.003(3) -0.008(3) 0.006(3) C3 0.015(4) 0.040(5) 0.009(4) -0.006(3) -0.002(3) -0.006(3) C4 0.020(4) 0.019(4) 0.021(4) 0.001(3) 0.003(3) 0.005(3) C5 0.018(4) 0.014(4) 0.021(4) 0.003(3) 0.010(3) 0.007(3) B1 0.024(4) 0.014(4) 0.021(4) 0.003(4) 0.003(4) -0.002(3) O1 0.021(3) 0.019(3) 0.022(3) -0.004(2) -0.005(2) 0.005(2) O2 0.026(3) 0.020(3) 0.023(3) 0.000(2) -0.002(2) 0.006(2) C6 0.021(4) 0.016(4) 0.018(3) 0.006(3) -0.006(3) 0.003(3) N1 0.022(4) 0.017(3) 0.017(3) 0.000(2) -0.003(3) -0.002(3) C7 0.046(6) 0.028(5) 0.021(4) -0.004(4) -0.008(4) -0.006(4) C8 0.023(4) 0.034(5) 0.020(4) 0.002(3) 0.002(4) 0.003(4) C9 0.036(5) 0.035(5) 0.025(4) 0.004(4) 0.007(4) -0.012(4) C10 0.045(5) 0.024(4) 0.023(4) 0.000(3) 0.009(4) -0.002(4) C11 0.045(6) 0.033(5) 0.011(4) 0.001(3) 0.003(4) -0.008(4) C12 0.033(6) 0.029(5) 0.020(5) 0.000(3) 0.020(4) -0.003(4) C13 0.027(4) 0.042(6) 0.034(5) 0.013(4) 0.023(4) 0.000(4) Fe2 0.0173(5) 0.0225(5) 0.0140(4) -0.0027(5) -0.0031(5) 0.0013(5) C14 0.022(5) 0.020(4) 0.003(3) -0.004(3) 0.000(3) 0.001(4) C15 0.029(5) 0.016(4) 0.017(4) -0.001(3) -0.001(3) 0.001(3) C16 0.015(4) 0.023(4) 0.028(5) 0.001(4) 0.006(3) -0.001(3) C17 0.008(4) 0.030(5) 0.019(4) -0.013(3) 0.002(3) 0.005(3) C18 0.024(4) 0.011(4) 0.015(4) -0.005(3) 0.001(3) -0.002(3) B2 0.024(5) 0.017(5) 0.021(4) -0.006(4) 0.002(4) -0.007(4) O3 0.017(3) 0.021(3) 0.019(3) 0.002(2) 0.009(2) 0.005(2) O4 0.020(3) 0.022(3) 0.023(2) 0.004(2) 0.008(2) 0.005(2) C19 0.024(4) 0.022(4) 0.019(4) 0.000(3) -0.004(3) 0.005(3) N2 0.020(3) 0.018(3) 0.016(3) 0.003(3) -0.008(3) -0.002(2) C20 0.043(4) 0.017(3) 0.020(4) 0.004(4) 0.000(4) 0.005(4) C21 0.027(4) 0.023(4) 0.017(4) -0.002(3) 0.001(3) 0.000(3) C22 0.044(6) 0.042(6) 0.030(6) -0.001(4) -0.024(5) 0.003(4) C23 0.034(5) 0.055(6) 0.010(4) -0.004(4) -0.009(4) -0.009(5) C24 0.031(5) 0.024(4) 0.021(4) -0.009(3) -0.010(4) 0.000(4) C25 0.022(4) 0.033(5) 0.017(4) -0.005(3) -0.012(3) -0.005(3) C26 0.024(4) 0.044(6) 0.032(5) -0.015(4) -0.008(4) 0.005(4) _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 C2 2.026(7) . ? Fe1 C13 2.028(8) . ? Fe1 C11 2.035(8) . ? Fe1 C12 2.037(9) . ? Fe1 C3 2.045(8) . ? Fe1 C1 2.048(8) . ? Fe1 C9 2.051(8) . ? Fe1 C4 2.053(7) . ? Fe1 C10 2.059(7) . ? Fe1 C5 2.065(7) . ? C1 C2 1.425(10) . ? C1 C5 1.446(10) . ? C1 B1 1.552(11) . ? C2 C3 1.439(10) . ? C3 C4 1.425(10) . ? C4 C5 1.401(10) . ? C5 C6 1.507(9) . ? B1 O2 1.370(9) . ? B1 O1 1.374(10) . ? C6 N1 1.475(8) . ? N1 C8 1.464(9) . ? N1 C7 1.469(9) . ? C9 C10 1.415(11) . ? C9 C13 1.430(11) . ? C10 C11 1.443(10) . ? C11 C12 1.437(12) . ? C12 C13 1.426(12) . ? Fe2 C22 2.023(9) . ? Fe2 C15 2.023(7) . ? Fe2 C26 2.029(8) . ? Fe2 C23 2.034(7) . ? Fe2 C14 2.035(7) . ? Fe2 C18 2.039(7) . ? Fe2 C16 2.039(7) . ? Fe2 C25 2.045(7) . ? Fe2 C17 2.048(7) . ? Fe2 C24 2.052(7) . ? C14 C15 1.421(9) . ? C14 C18 1.423(10) . ? C14 B2 1.592(11) . ? C15 C16 1.405(10) . ? C16 C17 1.401(10) . ? C17 C18 1.443(10) . ? C18 C19 1.517(10) . ? B2 O3 1.359(10) . ? B2 O4 1.365(10) . ? C19 N2 1.463(8) . ? N2 C20 1.459(9) . ? N2 C21 1.464(9) . ? C22 C26 1.373(13) . ? C22 C23 1.402(13) . ? C23 C24 1.439(11) . ? C24 C25 1.403(10) . ? C25 C26 1.431(11) . ? 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 C2 Fe1 C13 120.4(3) . . ? C2 Fe1 C11 122.2(3) . . ? C13 Fe1 C11 69.2(3) . . ? C2 Fe1 C12 105.1(3) . . ? C13 Fe1 C12 41.1(3) . . ? C11 Fe1 C12 41.3(3) . . ? C2 Fe1 C3 41.4(3) . . ? C13 Fe1 C3 156.6(3) . . ? C11 Fe1 C3 106.1(3) . . ? C12 Fe1 C3 120.4(3) . . ? C2 Fe1 C1 40.9(3) . . ? C13 Fe1 C1 106.2(3) . . ? C11 Fe1 C1 158.7(3) . . ? C12 Fe1 C1 121.6(3) . . ? C3 Fe1 C1 69.5(3) . . ? C2 Fe1 C9 157.4(3) . . ? C13 Fe1 C9 41.0(3) . . ? C11 Fe1 C9 68.8(3) . . ? C12 Fe1 C9 69.1(3) . . ? C3 Fe1 C9 160.4(3) . . ? C1 Fe1 C9 122.2(3) . . ? C2 Fe1 C4 68.6(3) . . ? C13 Fe1 C4 160.9(3) . . ? C11 Fe1 C4 122.3(3) . . ? C12 Fe1 C4 157.4(3) . . ? C3 Fe1 C4 40.7(3) . . ? C1 Fe1 C4 68.8(3) . . ? C9 Fe1 C4 124.9(3) . . ? C2 Fe1 C10 160.1(3) . . ? C13 Fe1 C10 68.8(3) . . ? C11 Fe1 C10 41.3(3) . . ? C12 Fe1 C10 69.4(3) . . ? C3 Fe1 C10 123.6(3) . . ? C1 Fe1 C10 158.2(3) . . ? C9 Fe1 C10 40.3(3) . . ? C4 Fe1 C10 108.6(3) . . ? C2 Fe1 C5 68.3(3) . . ? C13 Fe1 C5 124.6(3) . . ? C11 Fe1 C5 158.2(3) . . ? C12 Fe1 C5 160.0(3) . . ? C3 Fe1 C5 68.1(3) . . ? C1 Fe1 C5 41.2(3) . . ? C9 Fe1 C5 109.3(3) . . ? C4 Fe1 C5 39.8(3) . . ? C10 Fe1 C5 123.1(3) . . ? C2 C1 C5 106.3(6) . . ? C2 C1 B1 125.8(6) . . ? C5 C1 B1 128.0(7) . . ? C2 C1 Fe1 68.7(4) . . ? C5 C1 Fe1 70.0(4) . . ? B1 C1 Fe1 126.7(5) . . ? C1 C2 C3 109.0(6) . . ? C1 C2 Fe1 70.4(4) . . ? C3 C2 Fe1 70.0(4) . . ? C4 C3 C2 106.9(6) . . ? C4 C3 Fe1 70.0(4) . . ? C2 C3 Fe1 68.6(4) . . ? C5 C4 C3 108.9(7) . . ? C5 C4 Fe1 70.6(4) . . ? C3 C4 Fe1 69.4(4) . . ? C4 C5 C1 108.9(6) . . ? C4 C5 C6 126.3(6) . . ? C1 C5 C6 124.8(7) . . ? C4 C5 Fe1 69.6(4) . . ? C1 C5 Fe1 68.8(4) . . ? C6 C5 Fe1 127.4(5) . . ? O2 B1 O1 118.8(7) . . ? O2 B1 C1 120.4(7) . . ? O1 B1 C1 120.8(7) . . ? N1 C6 C5 111.6(5) . . ? C8 N1 C7 110.0(6) . . ? C8 N1 C6 111.8(6) . . ? C7 N1 C6 110.6(5) . . ? C10 C9 C13 108.5(7) . . ? C10 C9 Fe1 70.2(4) . . ? C13 C9 Fe1 68.6(4) . . ? C9 C10 C11 107.6(7) . . ? C9 C10 Fe1 69.5(4) . . ? C11 C10 Fe1 68.4(4) . . ? C12 C11 C10 108.1(8) . . ? C12 C11 Fe1 69.4(5) . . ? C10 C11 Fe1 70.3(4) . . ? C13 C12 C11 107.3(7) . . ? C13 C12 Fe1 69.1(5) . . ? C11 C12 Fe1 69.2(5) . . ? C12 C13 C9 108.5(8) . . ? C12 C13 Fe1 69.8(5) . . ? C9 C13 Fe1 70.4(4) . . ? C22 Fe2 C15 106.7(3) . . ? C22 Fe2 C26 39.6(4) . . ? C15 Fe2 C26 122.2(3) . . ? C22 Fe2 C23 40.4(4) . . ? C15 Fe2 C23 121.0(3) . . ? C26 Fe2 C23 68.0(3) . . ? C22 Fe2 C14 121.2(3) . . ? C15 Fe2 C14 41.0(3) . . ? C26 Fe2 C14 106.8(3) . . ? C23 Fe2 C14 156.7(3) . . ? C22 Fe2 C18 157.6(4) . . ? C15 Fe2 C18 68.6(3) . . ? C26 Fe2 C18 123.0(3) . . ? C23 Fe2 C18 160.9(3) . . ? C14 Fe2 C18 40.9(3) . . ? C22 Fe2 C16 123.1(4) . . ? C15 Fe2 C16 40.5(3) . . ? C26 Fe2 C16 158.1(3) . . ? C23 Fe2 C16 107.2(3) . . ? C14 Fe2 C16 68.6(3) . . ? C18 Fe2 C16 68.4(3) . . ? C22 Fe2 C25 67.7(3) . . ? C15 Fe2 C25 159.7(3) . . ? C26 Fe2 C25 41.1(3) . . ? C23 Fe2 C25 68.2(3) . . ? C14 Fe2 C25 123.8(3) . . ? C18 Fe2 C25 108.7(3) . . ? C16 Fe2 C25 159.0(3) . . ? C22 Fe2 C17 159.2(4) . . ? C15 Fe2 C17 68.2(3) . . ? C26 Fe2 C17 160.2(3) . . ? C23 Fe2 C17 123.5(3) . . ? C14 Fe2 C17 69.1(3) . . ? C18 Fe2 C17 41.3(3) . . ? C16 Fe2 C17 40.1(3) . . ? C25 Fe2 C17 124.0(3) . . ? C22 Fe2 C24 68.2(3) . . ? C15 Fe2 C24 158.0(3) . . ? C26 Fe2 C24 68.4(3) . . ? C23 Fe2 C24 41.2(3) . . ? C14 Fe2 C24 160.1(3) . . ? C18 Fe2 C24 124.3(3) . . ? C16 Fe2 C24 123.1(3) . . ? C25 Fe2 C24 40.0(3) . . ? C17 Fe2 C24 108.5(3) . . ? C15 C14 C18 107.2(6) . . ? C15 C14 B2 126.1(7) . . ? C18 C14 B2 126.4(6) . . ? C15 C14 Fe2 69.0(4) . . ? C18 C14 Fe2 69.7(4) . . ? B2 C14 Fe2 121.6(5) . . ? C16 C15 C14 108.8(7) . . ? C16 C15 Fe2 70.4(4) . . ? C14 C15 Fe2 70.0(4) . . ? C17 C16 C15 108.9(7) . . ? C17 C16 Fe2 70.3(4) . . ? C15 C16 Fe2 69.2(4) . . ? C16 C17 C18 107.5(6) . . ? C16 C17 Fe2 69.6(4) . . ? C18 C17 Fe2 69.0(4) . . ? C14 C18 C17 107.8(6) . . ? C14 C18 C19 126.4(6) . . ? C17 C18 C19 125.8(7) . . ? C14 C18 Fe2 69.4(4) . . ? C17 C18 Fe2 69.7(4) . . ? C19 C18 Fe2 126.1(5) . . ? O3 B2 O4 120.7(7) . . ? O3 B2 C14 121.8(7) . . ? O4 B2 C14 117.5(7) . . ? N2 C19 C18 113.1(6) . . ? C20 N2 C19 109.1(6) . . ? C20 N2 C21 111.4(6) . . ? C19 N2 C21 111.1(6) . . ? C26 C22 C23 109.9(8) . . ? C26 C22 Fe2 70.4(5) . . ? C23 C22 Fe2 70.2(5) . . ? C22 C23 C24 107.0(8) . . ? C22 C23 Fe2 69.4(5) . . ? C24 C23 Fe2 70.1(4) . . ? C25 C24 C23 107.2(7) . . ? C25 C24 Fe2 69.7(4) . . ? C23 C24 Fe2 68.7(4) . . ? C24 C25 C26 108.1(7) . . ? C24 C25 Fe2 70.2(4) . . ? C26 C25 Fe2 68.8(4) . . ? C22 C26 C25 107.7(8) . . ? C22 C26 Fe2 70.0(5) . . ? C25 C26 Fe2 70.1(4) . . ? _refine_diff_density_max 1.310 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.123 #===END data_B102377M-5 _database_code_CSD 160675 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C23 H32 B Fe N O2' _chemical_formula_weight 421.16 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.3162(15) _cell_length_b 11.887(2) _cell_length_c 12.622(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.73(3) _cell_angle_gamma 90.00 _cell_volume 1061.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method ? _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.728 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7453 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 29.52 _reflns_number_total 4780 _reflns_number_observed 4359 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+0.6663P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(2) _refine_ls_number_reflns 4779 _refine_ls_number_parameters 253 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_obs 0.0447 _refine_ls_wR_factor_all 0.1111 _refine_ls_wR_factor_obs 0.1077 _refine_ls_goodness_of_fit_all 1.037 _refine_ls_goodness_of_fit_obs 1.055 _refine_ls_restrained_S_all 1.038 _refine_ls_restrained_S_obs 1.055 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Fe Fe 0.46441(5) 0.48441(3) 0.30168(3) 0.01987(11) Uani 1 d . . C1 C 0.4768(4) 0.6518(3) 0.2684(3) 0.0190(6) Uani 1 d . . C2 C 0.6162(4) 0.6239(3) 0.3670(2) 0.0202(6) Uani 1 d . . H2 H 0.6237(4) 0.6561(3) 0.4412(2) 0.024 Uiso 1 calc R . C3 C 0.7377(4) 0.5399(3) 0.3428(3) 0.0217(6) Uani 1 d . . H3 H 0.8459(4) 0.5036(3) 0.3966(3) 0.026 Uiso 1 calc R . C4 C 0.6776(4) 0.5158(2) 0.2290(3) 0.0201(6) Uani 1 d . . H4 H 0.7366(4) 0.4594(2) 0.1891(3) 0.024 Uiso 1 calc R . C5 C 0.5149(4) 0.5834(3) 0.1815(3) 0.0199(6) Uani 1 d . . C6 C 0.4059(4) 0.5797(3) 0.0637(2) 0.0213(6) Uani 1 d . . H61 H 0.4069(4) 0.5012(3) 0.0376(2) 0.026 Uiso 1 calc R . H62 H 0.2729(4) 0.5995(3) 0.0599(2) 0.021 Uiso 1 calc R . N N 0.4719(4) 0.6527(2) -0.0120(2) 0.0255(6) Uani 1 d . . C7 C 0.6648(5) 0.6301(3) -0.0138(3) 0.0315(8) Uani 1 d . . H71 H 0.6768(5) 0.5512(3) -0.0335(3) 0.038 Uiso 1 calc R . H72 H 0.7485(5) 0.6449(3) 0.0587(3) 0.031 Uiso 1 calc R . H73 H 0.7000(5) 0.6789(3) -0.0680(3) 0.038 Uiso 1 calc R . C8 C 0.4430(6) 0.7708(3) 0.0070(3) 0.0319(8) Uani 1 d . . H81 H 0.3088(6) 0.7843(3) 0.0015(3) 0.038 Uiso 1 calc R . H82 H 0.4830(6) 0.8161(3) -0.0479(3) 0.032 Uiso 1 calc R . H83 H 0.5177(6) 0.7918(3) 0.0803(3) 0.038 Uiso 1 calc R . B B 0.3030(5) 0.7259(3) 0.2656(3) 0.0203(7) Uani 1 d . . O1 O 0.1423(3) 0.7285(2) 0.1814(2) 0.0241(5) Uani 1 d . . O2 O 0.2959(3) 0.7962(2) 0.3505(2) 0.0206(4) Uani 1 d . . C9 C 0.0116(4) 0.8072(3) 0.2093(2) 0.0209(6) Uani 1 d . . H9 H -0.1080(4) 0.7666(3) 0.2094(2) 0.025 Uiso 1 calc R . C10 C -0.0336(5) 0.9013(3) 0.1225(3) 0.0252(7) Uani 1 d . . H101 H 0.0348(5) 0.8859(3) 0.0657(3) 0.030 Uiso 1 calc R . H102 H -0.1706(5) 0.9000(3) 0.0865(3) 0.025 Uiso 1 calc R . C11 C 0.0199(4) 1.0174(3) 0.1694(3) 0.0230(7) Uani 1 d . . H11 H -0.0046(4) 1.0803(3) 0.1150(3) 0.028 Uiso 1 calc R . C12 C 0.2210(4) 1.0130(3) 0.2454(3) 0.0237(7) Uani 1 d . . H121 H 0.2839(4) 1.0872(3) 0.2598(3) 0.028 Uiso 1 calc R . H122 H 0.3043(4) 0.9565(3) 0.2239(3) 0.024 Uiso 1 calc R . C13 C 0.1287(4) 0.9729(3) 0.3362(2) 0.0187(6) Uani 1 d . . H13 H 0.1885(4) 1.0025(3) 0.4112(2) 0.022 Uiso 1 calc R . C14 C -0.0545(4) 1.0364(3) 0.2730(3) 0.0216(6) Uani 1 d . . C15 C -0.0473(5) 1.1604(3) 0.3062(3) 0.0323(8) Uani 1 d . . H151 H 0.0787(5) 1.1907(3) 0.3097(3) 0.039 Uiso 1 calc R . H152 H -0.0739(5) 1.1673(3) 0.3782(3) 0.032 Uiso 1 calc R . H153 H -0.1421(5) 1.2026(3) 0.2520(3) 0.039 Uiso 1 calc R . C16 C -0.2528(4) 0.9933(4) 0.2690(3) 0.0285(7) Uani 1 d . . H161 H -0.2672(4) 0.9167(4) 0.2394(3) 0.034 Uiso 1 calc R . H162 H -0.3467(4) 1.0426(4) 0.2219(3) 0.029 Uiso 1 calc R . H163 H -0.2718(4) 0.9930(4) 0.3431(3) 0.034 Uiso 1 calc R . C17 C 0.1078(4) 0.8459(3) 0.3284(2) 0.0188(6) Uani 1 d . . C18 C 0.0165(5) 0.7972(3) 0.4134(3) 0.0268(7) Uani 1 d . . H181 H -0.1084(5) 0.8312(3) 0.4050(3) 0.032 Uiso 1 calc R . H182 H 0.0959(5) 0.8133(3) 0.4868(3) 0.027 Uiso 1 calc R . H183 H 0.0029(5) 0.7156(3) 0.4032(3) 0.032 Uiso 1 calc R . C19 C 0.2566(5) 0.3770(3) 0.2253(3) 0.0328(8) Uani 1 d . . H19 H 0.2034(5) 0.3718(3) 0.1442(3) 0.039 Uiso 1 calc R . C20 C 0.4101(6) 0.3157(3) 0.2851(4) 0.0394(10) Uani 1 d . . H20 H 0.4845(6) 0.2588(3) 0.2553(4) 0.047 Uiso 1 calc R . C21 C 0.4413(7) 0.3483(5) 0.3954(4) 0.059(2) Uani 1 d . . H21 H 0.5421(7) 0.3185(5) 0.4582(4) 0.071 Uiso 1 calc R . C22 C 0.3056(8) 0.4308(5) 0.4018(4) 0.065(2) Uani 1 d . . H22 H 0.2922(8) 0.4693(5) 0.4699(4) 0.078 Uiso 1 calc R . C23 C 0.1910(5) 0.4486(3) 0.2944(4) 0.0391(9) Uani 1 d . . H23 H 0.0816(5) 0.5014(3) 0.2728(4) 0.047 Uiso 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 Fe 0.0159(2) 0.0220(2) 0.0212(2) 0.0035(2) 0.00391(13) -0.0027(2) C1 0.0169(15) 0.0185(15) 0.0197(14) 0.0000(12) 0.0009(12) -0.0014(12) C2 0.0133(13) 0.024(2) 0.0217(14) 0.0003(12) 0.0019(11) -0.0011(11) C3 0.0136(13) 0.024(2) 0.027(2) 0.0029(12) 0.0043(12) -0.0029(11) C4 0.0165(13) 0.020(2) 0.0246(14) 0.0012(11) 0.0061(11) -0.0004(10) C5 0.0179(14) 0.019(2) 0.0229(15) 0.0031(11) 0.0056(12) -0.0022(11) C6 0.0222(14) 0.0197(15) 0.0211(14) -0.0023(11) 0.0034(12) -0.0031(11) N 0.0339(15) 0.0233(14) 0.0192(12) -0.0016(11) 0.0066(11) -0.0006(11) C7 0.041(2) 0.032(2) 0.025(2) 0.0000(14) 0.0148(14) 0.000(2) C8 0.044(2) 0.022(2) 0.032(2) 0.0016(14) 0.013(2) -0.0002(15) B 0.022(2) 0.020(2) 0.0185(15) -0.0003(13) 0.0034(13) -0.0022(13) O1 0.0220(11) 0.0247(11) 0.0229(10) -0.0068(9) 0.0008(9) 0.0053(9) O2 0.0186(10) 0.0217(11) 0.0196(10) -0.0028(8) 0.0011(8) 0.0008(8) C9 0.0161(13) 0.023(2) 0.0221(14) -0.0050(12) 0.0024(11) 0.0006(11) C10 0.024(2) 0.030(2) 0.0192(14) -0.0005(13) 0.0021(12) 0.0075(13) C11 0.0233(15) 0.025(2) 0.0228(14) 0.0055(11) 0.0095(12) 0.0016(11) C12 0.0197(14) 0.025(2) 0.0269(15) 0.0055(12) 0.0075(12) -0.0026(11) C13 0.0193(12) 0.019(2) 0.0188(11) -0.0031(13) 0.0071(9) -0.0024(13) C14 0.0213(14) 0.023(2) 0.0218(14) -0.0002(12) 0.0076(12) -0.0019(12) C15 0.038(2) 0.024(2) 0.036(2) -0.0011(15) 0.011(2) 0.0033(15) C16 0.0200(12) 0.035(2) 0.0324(14) 0.000(2) 0.0105(11) 0.001(2) C17 0.0173(14) 0.0214(15) 0.0171(13) -0.0021(11) 0.0034(11) -0.0016(11) C18 0.031(2) 0.025(2) 0.026(2) 0.0035(13) 0.0105(13) -0.0032(13) C19 0.026(2) 0.035(2) 0.035(2) 0.004(2) 0.0032(15) -0.0150(15) C20 0.027(2) 0.025(2) 0.067(3) 0.009(2) 0.012(2) -0.005(2) C21 0.045(3) 0.068(3) 0.050(3) 0.038(3) -0.014(2) -0.033(2) C22 0.089(4) 0.079(4) 0.045(2) -0.026(2) 0.048(3) -0.062(3) C23 0.023(2) 0.038(2) 0.062(3) 0.002(2) 0.020(2) -0.0073(14) _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 Fe C22 2.024(4) . ? Fe C23 2.024(3) . ? Fe C5 2.027(3) . ? Fe C19 2.031(4) . ? Fe C4 2.035(3) . ? Fe C21 2.037(4) . ? Fe C1 2.040(3) . ? Fe C3 2.043(3) . ? Fe C20 2.045(4) . ? Fe C2 2.048(3) . ? C1 C2 1.433(4) . ? C1 C5 1.448(4) . ? C1 B 1.540(5) . ? C2 C3 1.421(4) . ? C3 C4 1.420(4) . ? C4 C5 1.435(4) . ? C5 C6 1.498(4) . ? C6 N 1.462(4) . ? N C7 1.443(5) . ? N C8 1.448(5) . ? B O2 1.370(4) . ? B O1 1.370(4) . ? O1 C9 1.444(4) . ? O2 C17 1.458(4) . ? C9 C10 1.542(5) . ? C9 C17 1.559(4) . ? C10 C11 1.514(5) . ? C11 C12 1.539(4) . ? C11 C14 1.556(4) . ? C12 C13 1.546(4) . ? C13 C17 1.518(5) . ? C13 C14 1.568(4) . ? C14 C16 1.527(4) . ? C14 C15 1.530(5) . ? C17 C18 1.515(4) . ? C19 C23 1.389(6) . ? C19 C20 1.390(6) . ? C20 C21 1.407(7) . ? C21 C22 1.412(8) . ? C22 C23 1.416(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C22 Fe C23 41.0(2) . . ? C22 Fe C5 153.2(2) . . ? C23 Fe C5 117.0(2) . . ? C22 Fe C19 67.7(2) . . ? C23 Fe C19 40.1(2) . . ? C5 Fe C19 105.43(14) . . ? C22 Fe C4 165.1(2) . . ? C23 Fe C4 151.7(2) . . ? C5 Fe C4 41.39(12) . . ? C19 Fe C4 117.91(14) . . ? C22 Fe C21 40.7(2) . . ? C23 Fe C21 68.4(2) . . ? C5 Fe C21 162.5(2) . . ? C19 Fe C21 67.3(2) . . ? C4 Fe C21 126.4(2) . . ? C22 Fe C1 119.9(2) . . ? C23 Fe C1 106.92(15) . . ? C5 Fe C1 41.72(12) . . ? C19 Fe C1 125.60(14) . . ? C4 Fe C1 69.46(12) . . ? C21 Fe C1 155.4(2) . . ? C22 Fe C3 128.5(2) . . ? C23 Fe C3 166.24(15) . . ? C5 Fe C3 69.51(12) . . ? C19 Fe C3 152.81(14) . . ? C4 Fe C3 40.76(12) . . ? C21 Fe C3 109.2(2) . . ? C1 Fe C3 69.25(12) . . ? C22 Fe C20 68.2(2) . . ? C23 Fe C20 68.0(2) . . ? C5 Fe C20 124.1(2) . . ? C19 Fe C20 39.9(2) . . ? C4 Fe C20 106.56(15) . . ? C21 Fe C20 40.3(2) . . ? C1 Fe C20 162.36(15) . . ? C3 Fe C20 119.65(15) . . ? C22 Fe C2 110.0(2) . . ? C23 Fe C2 128.08(15) . . ? C5 Fe C2 69.42(12) . . ? C19 Fe C2 164.48(14) . . ? C4 Fe C2 68.53(12) . . ? C21 Fe C2 121.7(2) . . ? C1 Fe C2 41.05(12) . . ? C3 Fe C2 40.64(12) . . ? C20 Fe C2 155.00(15) . . ? C2 C1 C5 107.3(3) . . ? C2 C1 B 123.6(3) . . ? C5 C1 B 128.4(3) . . ? C2 C1 Fe 69.8(2) . . ? C5 C1 Fe 68.7(2) . . ? B C1 Fe 118.9(2) . . ? C3 C2 C1 108.8(3) . . ? C3 C2 Fe 69.5(2) . . ? C1 C2 Fe 69.2(2) . . ? C4 C3 C2 108.0(3) . . ? C4 C3 Fe 69.3(2) . . ? C2 C3 Fe 69.9(2) . . ? C3 C4 C5 108.7(3) . . ? C3 C4 Fe 69.9(2) . . ? C5 C4 Fe 69.0(2) . . ? C4 C5 C1 107.2(3) . . ? C4 C5 C6 125.0(3) . . ? C1 C5 C6 127.7(3) . . ? C4 C5 Fe 69.6(2) . . ? C1 C5 Fe 69.6(2) . . ? C6 C5 Fe 125.0(2) . . ? N C6 C5 116.8(3) . . ? C7 N C8 111.6(3) . . ? C7 N C6 112.8(3) . . ? C8 N C6 112.4(3) . . ? O2 B O1 113.4(3) . . ? O2 B C1 121.8(3) . . ? O1 B C1 124.8(3) . . ? B O1 C9 108.5(2) . . ? B O2 C17 108.6(2) . . ? O1 C9 C10 109.4(2) . . ? O1 C9 C17 105.2(2) . . ? C10 C9 C17 115.7(3) . . ? C11 C10 C9 113.3(3) . . ? C10 C11 C12 108.9(3) . . ? C10 C11 C14 110.5(3) . . ? C12 C11 C14 87.9(2) . . ? C11 C12 C13 86.8(2) . . ? C17 C13 C12 108.3(2) . . ? C17 C13 C14 112.7(2) . . ? C12 C13 C14 87.3(2) . . ? C16 C14 C15 107.4(3) . . ? C16 C14 C11 117.1(3) . . ? C15 C14 C11 112.0(3) . . ? C16 C14 C13 122.5(3) . . ? C15 C14 C13 111.0(3) . . ? C11 C14 C13 85.5(2) . . ? O2 C17 C18 105.9(2) . . ? O2 C17 C13 108.4(2) . . ? C18 C17 C13 112.9(2) . . ? O2 C17 C9 103.7(2) . . ? C18 C17 C9 113.4(3) . . ? C13 C17 C9 111.7(2) . . ? C23 C19 C20 109.9(4) . . ? C23 C19 Fe 69.7(2) . . ? C20 C19 Fe 70.6(2) . . ? C19 C20 C21 107.4(4) . . ? C19 C20 Fe 69.5(2) . . ? C21 C20 Fe 69.5(3) . . ? C20 C21 C22 107.9(4) . . ? C20 C21 Fe 70.1(2) . . ? C22 C21 Fe 69.2(3) . . ? C21 C22 C23 107.6(4) . . ? C21 C22 Fe 70.1(2) . . ? C23 C22 Fe 69.5(2) . . ? C19 C23 C22 107.2(4) . . ? C19 C23 Fe 70.2(2) . . ? C22 C23 Fe 69.5(2) . . ? _refine_diff_density_max 0.481 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.061 #===END #------------------------------------------------------------