# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_meimeco01_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Fe N4 O3' _chemical_formula_weight 344.16 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.300(2) _cell_length_b 10.581(2) _cell_length_c 15.189(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.230(2) _cell_angle_gamma 90.00 _cell_volume 1611.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.952 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8324 _exptl_absorpt_correction_T_max 0.9629 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '\f and \w scans' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19311 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3988 _reflns_number_gt 3653 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _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^)+(0.0389P)^2^+0.6149P] 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 3988 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0746 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _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 0.727370(17) 0.619356(16) 0.122222(11) 0.01878(7) Uani 1 1 d . . . N1 N 0.69015(12) 0.58482(11) 0.01246(8) 0.0260(2) Uani 1 1 d . . . N2 N 0.80293(12) 0.51369(11) 0.19717(8) 0.0259(2) Uani 1 1 d . . . N3 N 0.91339(10) 0.81052(10) 0.23113(7) 0.0175(2) Uani 1 1 d . . . N4 N 0.88956(10) 0.84753(10) 0.08982(7) 0.0173(2) Uani 1 1 d . . . O1 O 0.66242(14) 0.54684(13) -0.06222(8) 0.0469(3) Uani 1 1 d . . . O2 O 0.85998(12) 0.43658(11) 0.24786(9) 0.0434(3) Uani 1 1 d . . . O3 O 0.47383(12) 0.71778(12) 0.15714(10) 0.0461(3) Uani 1 1 d . . . C1 C 0.84538(12) 0.77017(11) 0.14867(8) 0.0159(2) Uani 1 1 d . . . C2 C 0.89928(14) 0.75882(13) 0.31762(8) 0.0226(3) Uani 1 1 d . . . H2A H 0.8095 0.7297 0.3121 0.034 Uiso 1 1 calc R . . H2B H 0.9191 0.8233 0.3632 0.034 Uiso 1 1 calc R . . H2C H 0.9600 0.6895 0.3345 0.034 Uiso 1 1 calc R . . C3 C 0.99780(13) 0.90986(12) 0.22411(9) 0.0222(2) Uani 1 1 d . . . H3 H 1.0540 0.9522 0.2716 0.027 Uiso 1 1 calc R . . C4 C 0.98294(13) 0.93335(12) 0.13537(8) 0.0227(3) Uani 1 1 d . . . H4 H 1.0267 0.9951 0.1096 0.027 Uiso 1 1 calc R . . C5 C 0.57405(14) 0.68400(13) 0.14641(10) 0.0270(3) Uani 1 1 d . . . C6 C 0.83545(12) 0.85399(12) -0.00611(8) 0.0171(2) Uani 1 1 d . . . C7 C 0.73725(12) 0.94504(12) -0.03781(9) 0.0207(2) Uani 1 1 d . . . C8 C 0.68722(13) 0.95391(13) -0.13075(9) 0.0237(3) Uani 1 1 d . . . H8 H 0.6226 1.0144 -0.1532 0.028 Uiso 1 1 calc R . . C9 C 0.73126(13) 0.87484(13) -0.19098(9) 0.0229(3) Uani 1 1 d . . . C10 C 0.82876(14) 0.78583(12) -0.15695(8) 0.0222(3) Uani 1 1 d . . . H10 H 0.8581 0.7322 -0.1969 0.027 Uiso 1 1 calc R . . C11 C 0.88410(13) 0.77454(11) -0.06431(8) 0.0195(2) Uani 1 1 d . . . C12 C 0.99342(16) 0.68060(14) -0.02947(10) 0.0296(3) Uani 1 1 d . . . H12A H 1.0701 0.7239 0.0053 0.044 Uiso 1 1 calc R . . H12B H 1.0169 0.6383 -0.0795 0.044 Uiso 1 1 calc R . . H12C H 0.9630 0.6196 0.0081 0.044 Uiso 1 1 calc R . . C13 C 0.68804(15) 1.03182(15) 0.02642(10) 0.0318(3) Uani 1 1 d . . . H13A H 0.7582 1.0888 0.0540 0.048 Uiso 1 1 calc R . . H13B H 0.6616 0.9826 0.0725 0.048 Uiso 1 1 calc R . . H13C H 0.6130 1.0794 -0.0063 0.048 Uiso 1 1 calc R . . C14 C 0.67454(15) 0.88651(16) -0.29157(9) 0.0316(3) Uani 1 1 d . . . H14A H 0.7158 0.9565 -0.3148 0.047 Uiso 1 1 calc R . . H14B H 0.5801 0.9004 -0.3028 0.047 Uiso 1 1 calc R . . H14C H 0.6917 0.8101 -0.3211 0.047 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 0.02194(11) 0.01695(10) 0.01706(10) 0.00130(6) 0.00366(7) -0.00515(6) N1 0.0295(6) 0.0258(6) 0.0219(5) -0.0028(4) 0.0043(4) -0.0052(5) N2 0.0283(6) 0.0217(5) 0.0264(6) 0.0045(4) 0.0033(5) -0.0077(4) N3 0.0207(5) 0.0181(5) 0.0137(5) 0.0003(4) 0.0041(4) -0.0016(4) N4 0.0203(5) 0.0180(5) 0.0133(5) 0.0003(4) 0.0036(4) -0.0049(4) O1 0.0582(8) 0.0563(8) 0.0233(5) -0.0147(5) 0.0032(5) -0.0104(6) O2 0.0428(7) 0.0323(6) 0.0471(7) 0.0194(5) -0.0064(5) -0.0048(5) O3 0.0330(6) 0.0438(7) 0.0671(9) -0.0148(6) 0.0226(6) -0.0052(5) C1 0.0177(5) 0.0161(5) 0.0141(5) 0.0012(4) 0.0043(4) -0.0001(4) C2 0.0294(6) 0.0251(6) 0.0134(5) 0.0034(5) 0.0051(5) 0.0009(5) C3 0.0250(6) 0.0215(6) 0.0186(6) -0.0023(5) 0.0019(5) -0.0073(5) C4 0.0255(6) 0.0223(6) 0.0194(6) 0.0000(5) 0.0034(5) -0.0101(5) C5 0.0283(7) 0.0241(6) 0.0305(7) -0.0048(5) 0.0103(5) -0.0084(5) C6 0.0197(5) 0.0184(5) 0.0131(5) 0.0020(4) 0.0034(4) -0.0060(4) C7 0.0200(6) 0.0225(6) 0.0200(6) 0.0011(5) 0.0053(5) -0.0029(5) C8 0.0186(6) 0.0285(7) 0.0225(6) 0.0057(5) 0.0015(5) -0.0020(5) C9 0.0217(6) 0.0302(7) 0.0155(6) 0.0030(5) 0.0013(5) -0.0108(5) C10 0.0297(6) 0.0223(6) 0.0155(5) -0.0018(4) 0.0071(5) -0.0069(5) C11 0.0248(6) 0.0178(5) 0.0162(5) 0.0019(4) 0.0054(5) -0.0037(5) C12 0.0391(8) 0.0271(7) 0.0236(6) 0.0028(5) 0.0096(6) 0.0092(6) C13 0.0328(7) 0.0350(8) 0.0285(7) -0.0026(6) 0.0086(6) 0.0082(6) C14 0.0285(7) 0.0471(9) 0.0164(6) 0.0049(6) -0.0005(5) -0.0092(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N2 1.6572(12) . ? Fe1 N1 1.6635(12) . ? Fe1 C5 1.8337(15) . ? Fe1 C1 1.9905(12) . ? N1 O1 1.1754(16) . ? N2 O2 1.1818(16) . ? N3 C1 1.3565(15) . ? N3 C3 1.3837(16) . ? N3 C2 1.4607(15) . ? N4 C1 1.3647(15) . ? N4 C4 1.3870(15) . ? N4 C6 1.4375(15) . ? O3 C5 1.1388(19) . ? C3 C4 1.3444(18) . ? C6 C11 1.3936(17) . ? C6 C7 1.4001(18) . ? C7 C8 1.3907(18) . ? C7 C13 1.5094(19) . ? C8 C9 1.390(2) . ? C9 C10 1.3876(19) . ? C9 C14 1.5107(18) . ? C10 C11 1.3972(17) . ? C11 C12 1.5043(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Fe1 N1 120.30(6) . . ? N2 Fe1 C5 113.87(6) . . ? N1 Fe1 C5 105.74(6) . . ? N2 Fe1 C1 103.48(5) . . ? N1 Fe1 C1 111.62(5) . . ? C5 Fe1 C1 100.06(6) . . ? O1 N1 Fe1 172.60(12) . . ? O2 N2 Fe1 177.01(13) . . ? C1 N3 C3 111.63(10) . . ? C1 N3 C2 125.16(10) . . ? C3 N3 C2 123.19(10) . . ? C1 N4 C4 111.29(10) . . ? C1 N4 C6 125.61(10) . . ? C4 N4 C6 122.56(10) . . ? N3 C1 N4 103.70(10) . . ? N3 C1 Fe1 126.95(8) . . ? N4 C1 Fe1 128.94(9) . . ? C4 C3 N3 106.76(11) . . ? C3 C4 N4 106.61(11) . . ? O3 C5 Fe1 174.99(13) . . ? C11 C6 C7 122.23(11) . . ? C11 C6 N4 120.13(11) . . ? C7 C6 N4 117.60(11) . . ? C8 C7 C6 117.79(12) . . ? C8 C7 C13 120.92(12) . . ? C6 C7 C13 121.29(12) . . ? C9 C8 C7 121.77(12) . . ? C10 C9 C8 118.73(12) . . ? C10 C9 C14 120.77(13) . . ? C8 C9 C14 120.50(13) . . ? C9 C10 C11 121.79(12) . . ? C6 C11 C10 117.66(12) . . ? C6 C11 C12 121.62(11) . . ? C10 C11 C12 120.71(12) . . ? 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 N2 Fe1 N1 O1 30.6(10) . . . . ? C5 Fe1 N1 O1 -100.1(10) . . . . ? C1 Fe1 N1 O1 152.0(9) . . . . ? N1 Fe1 N2 O2 36(2) . . . . ? C5 Fe1 N2 O2 163(2) . . . . ? C1 Fe1 N2 O2 -90(2) . . . . ? C3 N3 C1 N4 -0.15(14) . . . . ? C2 N3 C1 N4 178.75(11) . . . . ? C3 N3 C1 Fe1 172.98(9) . . . . ? C2 N3 C1 Fe1 -8.12(17) . . . . ? C4 N4 C1 N3 0.11(14) . . . . ? C6 N4 C1 N3 -171.65(11) . . . . ? C4 N4 C1 Fe1 -172.84(9) . . . . ? C6 N4 C1 Fe1 15.40(18) . . . . ? N2 Fe1 C1 N3 -36.56(12) . . . . ? N1 Fe1 C1 N3 -167.33(10) . . . . ? C5 Fe1 C1 N3 81.16(11) . . . . ? N2 Fe1 C1 N4 134.86(11) . . . . ? N1 Fe1 C1 N4 4.08(13) . . . . ? C5 Fe1 C1 N4 -107.43(12) . . . . ? C1 N3 C3 C4 0.14(15) . . . . ? C2 N3 C3 C4 -178.79(12) . . . . ? N3 C3 C4 N4 -0.07(15) . . . . ? C1 N4 C4 C3 -0.03(15) . . . . ? C6 N4 C4 C3 172.03(12) . . . . ? N2 Fe1 C5 O3 -96.4(16) . . . . ? N1 Fe1 C5 O3 37.8(16) . . . . ? C1 Fe1 C5 O3 153.8(16) . . . . ? C1 N4 C6 C11 -88.66(15) . . . . ? C4 N4 C6 C11 100.45(15) . . . . ? C1 N4 C6 C7 93.60(15) . . . . ? C4 N4 C6 C7 -77.28(15) . . . . ? C11 C6 C7 C8 0.61(18) . . . . ? N4 C6 C7 C8 178.29(11) . . . . ? C11 C6 C7 C13 -178.76(12) . . . . ? N4 C6 C7 C13 -1.08(18) . . . . ? C6 C7 C8 C9 0.64(18) . . . . ? C13 C7 C8 C9 -179.99(13) . . . . ? C7 C8 C9 C10 -0.68(19) . . . . ? C7 C8 C9 C14 179.76(12) . . . . ? C8 C9 C10 C11 -0.51(19) . . . . ? C14 C9 C10 C11 179.04(12) . . . . ? C7 C6 C11 C10 -1.73(18) . . . . ? N4 C6 C11 C10 -179.36(11) . . . . ? C7 C6 C11 C12 177.58(12) . . . . ? N4 C6 C11 C12 -0.05(18) . . . . ? C9 C10 C11 C6 1.68(18) . . . . ? C9 C10 C11 C12 -177.64(12) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.440 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 948616' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_datax _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H38 Fe N6 O2' _chemical_formula_weight 558.50 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 Orthorhombic _symmetry_space_group_name_H-M Pnn2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 12.373(2) _cell_length_b 23.135(4) _cell_length_c 9.6348(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2757.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.584 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9547 _exptl_absorpt_correction_T_max 0.9714 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25394 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4874 _reflns_number_gt 4731 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _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^)+(0.0477P)^2^+0.7854P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.009(13) _refine_ls_number_reflns 4874 _refine_ls_number_parameters 351 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0783 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.63771(2) 0.270228(11) 0.30157(4) 0.01663(9) Uani 1 1 d . . . N1 N 0.59737(13) 0.20225(7) 0.3090(2) 0.0244(4) Uani 1 1 d . . . N2 N 0.54875(14) 0.32162(8) 0.33375(18) 0.0231(4) Uani 1 1 d . . . O1 O 0.55862(13) 0.15486(7) 0.3210(2) 0.0361(4) Uani 1 1 d . . . O2 O 0.47396(14) 0.35320(8) 0.35936(19) 0.0400(4) Uani 1 1 d . . . C1 C 0.71664(16) 0.28618(9) 0.1251(2) 0.0190(4) Uani 1 1 d . . . C2 C 0.76752(17) 0.27777(9) 0.4210(2) 0.0184(4) Uani 1 1 d . . . C3 C 0.8060(2) 0.33159(11) -0.0522(3) 0.0313(5) Uani 1 1 d . . . H3 H 0.8393 0.3604 -0.1043 0.038 Uiso 1 1 calc R . . C4 C 0.7934(2) 0.27637(11) -0.0879(3) 0.0321(6) Uani 1 1 d . . . H4 H 0.8169 0.2592 -0.1698 0.039 Uiso 1 1 calc R . . C5 C 0.92453(18) 0.25822(10) 0.5348(2) 0.0249(5) Uani 1 1 d . . . H5 H 0.9864 0.2389 0.5638 0.030 Uiso 1 1 calc R . . C6 C 0.89068(19) 0.31022(10) 0.5778(2) 0.0247(5) Uani 1 1 d . . . H6 H 0.9248 0.3340 0.6421 0.030 Uiso 1 1 calc R . . C7 C 0.75727(18) 0.39157(9) 0.1518(2) 0.0193(4) Uani 1 1 d . . . C8 C 0.66479(18) 0.42592(9) 0.1445(2) 0.0217(4) Uani 1 1 d . . . C9 C 0.66529(19) 0.47809(9) 0.2184(3) 0.0244(5) Uani 1 1 d . . . H9 H 0.6040 0.5013 0.2159 0.029 Uiso 1 1 calc R . . C10 C 0.75265(17) 0.49615(8) 0.2941(3) 0.0237(4) Uani 1 1 d . . . C11 C 0.84485(16) 0.46188(9) 0.2942(3) 0.0259(5) Uani 1 1 d . . . H11 H 0.9056 0.4744 0.3425 0.031 Uiso 1 1 calc R . . C12 C 0.84884(17) 0.40934(10) 0.2240(2) 0.0226(5) Uani 1 1 d . . . C13 C 0.95080(18) 0.37327(11) 0.2275(3) 0.0326(5) Uani 1 1 d . . . H13A H 0.9401 0.3406 0.2873 0.049 Uiso 1 1 calc R . . H13B H 1.0096 0.3963 0.2619 0.049 Uiso 1 1 calc R . . H13C H 0.9674 0.3601 0.1355 0.049 Uiso 1 1 calc R . . C14 C 0.5687(2) 0.40825(11) 0.0585(3) 0.0310(5) Uani 1 1 d . . . H14A H 0.5932 0.3910 -0.0265 0.046 Uiso 1 1 calc R . . H14B H 0.5256 0.4417 0.0380 0.046 Uiso 1 1 calc R . . H14C H 0.5261 0.3808 0.1093 0.046 Uiso 1 1 calc R . . C15 C 0.7504(2) 0.55127(10) 0.3772(3) 0.0319(5) Uani 1 1 d . . . H15A H 0.6871 0.5731 0.3532 0.048 Uiso 1 1 calc R . . H15B H 0.8138 0.5736 0.3570 0.048 Uiso 1 1 calc R . . H15C H 0.7487 0.5422 0.4744 0.048 Uiso 1 1 calc R . . C16 C 0.7109(2) 0.18816(10) 0.0140(3) 0.0276(5) Uani 1 1 d . . . H16A H 0.7080 0.1732 0.1068 0.041 Uiso 1 1 calc R . . H16B H 0.7644 0.1674 -0.0383 0.041 Uiso 1 1 calc R . . H16C H 0.6416 0.1837 -0.0294 0.041 Uiso 1 1 calc R . . C17 C 0.85191(16) 0.18075(9) 0.3832(2) 0.0215(5) Uani 1 1 d . . . C18 C 0.91317(17) 0.16862(9) 0.2666(2) 0.0223(5) Uani 1 1 d . . . C19 C 0.91463(19) 0.11184(10) 0.2173(3) 0.0280(5) Uani 1 1 d . . . H19 H 0.9552 0.1029 0.1389 0.034 Uiso 1 1 calc R . . C20 C 0.85641(18) 0.06839(10) 0.2835(3) 0.0309(6) Uani 1 1 d . . . C21 C 0.79796(19) 0.08234(10) 0.4031(3) 0.0303(5) Uani 1 1 d . . . H21 H 0.7601 0.0534 0.4491 0.036 Uiso 1 1 calc R . . C22 C 0.79482(18) 0.13815(10) 0.4551(2) 0.0263(5) Uani 1 1 d . . . C23 C 0.7334(2) 0.15215(12) 0.5841(3) 0.0358(6) Uani 1 1 d . . . H23A H 0.6908 0.1193 0.6111 0.054 Uiso 1 1 calc R . . H23B H 0.6867 0.1845 0.5671 0.054 Uiso 1 1 calc R . . H23C H 0.7831 0.1616 0.6571 0.054 Uiso 1 1 calc R . . C24 C 0.9787(2) 0.21461(10) 0.1946(3) 0.0283(5) Uani 1 1 d . . . H24A H 0.9335 0.2474 0.1754 0.043 Uiso 1 1 calc R . . H24B H 1.0069 0.1995 0.1092 0.043 Uiso 1 1 calc R . . H24C H 1.0375 0.2262 0.2534 0.043 Uiso 1 1 calc R . . C25 C 0.8572(2) 0.00679(12) 0.2297(4) 0.0448(7) Uani 1 1 d . . . H25A H 0.8937 0.0055 0.1418 0.067 Uiso 1 1 calc R . . H25B H 0.7843 -0.0065 0.2184 0.067 Uiso 1 1 calc R . . H25C H 0.8942 -0.0177 0.2947 0.067 Uiso 1 1 calc R . . C26 C 0.72911(18) 0.37239(9) 0.5364(3) 0.0253(5) Uani 1 1 d . . . H26A H 0.6946 0.3848 0.4524 0.038 Uiso 1 1 calc R . . H26B H 0.7740 0.4029 0.5714 0.038 Uiso 1 1 calc R . . H26C H 0.6751 0.3628 0.6042 0.038 Uiso 1 1 calc R . . C27 C 0.4105(3) 0.04400(19) 0.2798(5) 0.0828(13) Uani 1 1 d . . . H27A H 0.3409 0.0257 0.2647 0.099 Uiso 1 1 calc R . . H27B H 0.4008 0.0856 0.2813 0.099 Uiso 1 1 calc R . . C28 C 0.4855(6) 0.0275(2) 0.1771(8) 0.133(3) Uani 1 1 d . . . H28A H 0.4551 0.0365 0.0869 0.160 Uiso 1 1 calc R . . H28B H 0.5501 0.0508 0.1883 0.160 Uiso 1 1 calc R . . C29 C 0.4621(7) 0.0229(2) 0.4125(7) 0.144(3) Uani 1 1 d . . . H29A H 0.4973 0.0559 0.4550 0.173 Uiso 1 1 calc R . . H29B H 0.4038 0.0116 0.4742 0.173 Uiso 1 1 calc R . . N3 N 0.73964(15) 0.24951(8) 0.0183(2) 0.0228(4) Uani 1 1 d . . . N4 N 0.75926(15) 0.33770(8) 0.0787(2) 0.0216(4) Uani 1 1 d . . . N5 N 0.84951(15) 0.23887(8) 0.4390(2) 0.0200(4) Uani 1 1 d . . . N6 N 0.79514(14) 0.32177(8) 0.50810(19) 0.0208(4) 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 0.01323(14) 0.01921(14) 0.01744(14) 0.00189(14) -0.00144(13) 0.00001(10) N1 0.0177(8) 0.0270(9) 0.0283(9) 0.0065(10) -0.0062(9) -0.0029(7) N2 0.0199(9) 0.0293(9) 0.0199(10) 0.0026(7) 0.0018(7) 0.0040(7) O1 0.0308(8) 0.0265(8) 0.0509(12) 0.0137(8) -0.0148(9) -0.0109(7) O2 0.0318(9) 0.0508(11) 0.0374(10) 0.0058(8) 0.0081(8) 0.0229(8) C1 0.0148(10) 0.0199(10) 0.0222(11) -0.0018(9) -0.0023(8) -0.0011(8) C2 0.0155(10) 0.0235(11) 0.0162(10) 0.0025(8) 0.0005(8) -0.0011(8) C3 0.0422(15) 0.0290(12) 0.0227(12) -0.0029(10) 0.0131(11) -0.0049(11) C4 0.0401(15) 0.0344(13) 0.0218(12) -0.0070(10) 0.0107(11) 0.0003(11) C5 0.0191(10) 0.0335(12) 0.0220(11) 0.0001(10) -0.0043(9) 0.0003(9) C6 0.0212(11) 0.0311(12) 0.0217(11) -0.0014(9) -0.0059(9) -0.0045(9) C7 0.0231(11) 0.0155(10) 0.0194(10) -0.0004(8) 0.0054(9) -0.0030(8) C8 0.0230(10) 0.0216(11) 0.0203(10) 0.0048(8) 0.0007(9) -0.0017(9) C9 0.0252(11) 0.0186(10) 0.0294(12) 0.0045(9) 0.0042(10) 0.0046(9) C10 0.0280(10) 0.0162(9) 0.0269(11) -0.0007(10) 0.0062(11) -0.0022(7) C11 0.0215(10) 0.0238(10) 0.0324(12) -0.0060(12) 0.0053(12) -0.0062(8) C12 0.0187(10) 0.0212(11) 0.0280(12) 0.0010(10) 0.0043(9) -0.0011(8) C13 0.0208(11) 0.0307(12) 0.0464(14) -0.0064(11) 0.0016(11) 0.0011(10) C14 0.0296(12) 0.0325(13) 0.0308(13) 0.0035(10) -0.0088(10) -0.0007(10) C15 0.0400(14) 0.0200(12) 0.0355(14) -0.0051(10) 0.0082(11) -0.0023(10) C16 0.0314(13) 0.0205(11) 0.0308(12) -0.0062(10) 0.0000(11) 0.0004(10) C17 0.0162(10) 0.0228(11) 0.0256(12) 0.0016(9) -0.0089(9) 0.0035(8) C18 0.0207(11) 0.0251(11) 0.0212(12) 0.0005(8) -0.0052(8) 0.0047(9) C19 0.0276(12) 0.0260(12) 0.0304(12) -0.0048(10) -0.0044(10) 0.0095(9) C20 0.0293(11) 0.0242(11) 0.0392(16) -0.0019(12) -0.0128(11) 0.0039(9) C21 0.0272(12) 0.0247(12) 0.0390(14) 0.0108(10) -0.0093(11) -0.0027(10) C22 0.0224(11) 0.0300(12) 0.0264(12) 0.0064(10) -0.0096(10) 0.0033(9) C23 0.0354(14) 0.0416(15) 0.0303(13) 0.0125(12) 0.0004(11) -0.0012(11) C24 0.0301(13) 0.0277(11) 0.0272(12) -0.0017(10) 0.0057(10) 0.0023(10) C25 0.0503(17) 0.0270(14) 0.0573(18) -0.0029(13) -0.0159(15) 0.0010(11) C26 0.0249(11) 0.0234(11) 0.0275(12) -0.0055(10) 0.0003(10) 0.0003(9) C27 0.063(2) 0.069(2) 0.116(4) -0.007(3) -0.025(3) 0.0099(19) C28 0.142(5) 0.100(4) 0.158(6) -0.049(4) -0.072(5) 0.067(4) C29 0.229(9) 0.069(3) 0.134(6) 0.002(3) 0.061(6) 0.027(4) N3 0.0261(10) 0.0198(9) 0.0226(9) -0.0054(8) 0.0023(8) -0.0013(8) N4 0.0242(10) 0.0204(9) 0.0202(9) -0.0017(8) 0.0040(8) -0.0024(8) N5 0.0175(9) 0.0236(9) 0.0190(9) 0.0011(7) -0.0024(7) 0.0013(7) N6 0.0180(9) 0.0238(9) 0.0205(9) -0.0015(8) -0.0008(8) 0.0005(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N2 1.6496(18) . ? Fe1 N1 1.6514(17) . ? Fe1 C2 1.984(2) . ? Fe1 C1 1.995(2) . ? N1 O1 1.202(2) . ? N2 O2 1.204(2) . ? C1 N3 1.364(3) . ? C1 N4 1.378(3) . ? C2 N6 1.363(3) . ? C2 N5 1.367(3) . ? C3 C4 1.332(3) . ? C3 N4 1.395(3) . ? C3 H3 0.9300 . ? C4 N3 1.369(3) . ? C4 H4 0.9300 . ? C5 C6 1.339(3) . ? C5 N5 1.384(3) . ? C5 H5 0.9300 . ? C6 N6 1.386(3) . ? C6 H6 0.9300 . ? C7 C12 1.391(3) . ? C7 C8 1.395(3) . ? C7 N4 1.432(3) . ? C8 C9 1.401(3) . ? C8 C14 1.506(3) . ? C9 C10 1.369(3) . ? C9 H9 0.9300 . ? C10 C11 1.389(3) . ? C10 C15 1.506(3) . ? C11 C12 1.392(3) . ? C11 H11 0.9300 . ? C12 C13 1.513(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N3 1.464(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.383(3) . ? C17 C22 1.396(3) . ? C17 N5 1.448(3) . ? C18 C19 1.397(3) . ? C18 C24 1.507(3) . ? C19 C20 1.392(4) . ? C19 H19 0.9300 . ? C20 C21 1.398(4) . ? C20 C25 1.517(3) . ? C21 C22 1.385(3) . ? C21 H21 0.9300 . ? C22 C23 1.493(4) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 N6 1.454(3) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.410(8) . ? C27 C29 1.511(8) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C28 1.321(10) 2_655 ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C29 1.415(13) 2_655 ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Fe1 N1 118.46(9) . . ? N2 Fe1 C2 111.57(9) . . ? N1 Fe1 C2 107.66(9) . . ? N2 Fe1 C1 110.70(9) . . ? N1 Fe1 C1 111.16(10) . . ? C2 Fe1 C1 94.70(9) . . ? O1 N1 Fe1 173.29(18) . . ? O2 N2 Fe1 171.19(18) . . ? N3 C1 N4 102.31(18) . . ? N3 C1 Fe1 129.06(16) . . ? N4 C1 Fe1 128.60(15) . . ? N6 C2 N5 103.18(18) . . ? N6 C2 Fe1 128.75(16) . . ? N5 C2 Fe1 128.04(16) . . ? C4 C3 N4 106.4(2) . . ? C4 C3 H3 126.8 . . ? N4 C3 H3 126.8 . . ? C3 C4 N3 107.4(2) . . ? C3 C4 H4 126.3 . . ? N3 C4 H4 126.3 . . ? C6 C5 N5 106.7(2) . . ? C6 C5 H5 126.7 . . ? N5 C5 H5 126.7 . . ? C5 C6 N6 106.9(2) . . ? C5 C6 H6 126.6 . . ? N6 C6 H6 126.6 . . ? C12 C7 C8 121.7(2) . . ? C12 C7 N4 119.3(2) . . ? C8 C7 N4 119.0(2) . . ? C7 C8 C9 117.5(2) . . ? C7 C8 C14 121.4(2) . . ? C9 C8 C14 121.1(2) . . ? C10 C9 C8 122.5(2) . . ? C10 C9 H9 118.8 . . ? C8 C9 H9 118.8 . . ? C9 C10 C11 118.3(2) . . ? C9 C10 C15 121.8(2) . . ? C11 C10 C15 119.9(2) . . ? C10 C11 C12 121.8(2) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C7 C12 C11 118.2(2) . . ? C7 C12 C13 121.8(2) . . ? C11 C12 C13 120.0(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 122.4(2) . . ? C18 C17 N5 120.1(2) . . ? C22 C17 N5 117.4(2) . . ? C17 C18 C19 118.3(2) . . ? C17 C18 C24 121.7(2) . . ? C19 C18 C24 120.0(2) . . ? C20 C19 C18 121.1(2) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 118.6(2) . . ? C19 C20 C25 121.2(3) . . ? C21 C20 C25 120.2(3) . . ? C22 C21 C20 121.8(2) . . ? C22 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? C21 C22 C17 117.7(2) . . ? C21 C22 C23 121.1(2) . . ? C17 C22 C23 121.2(2) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C18 C24 H24A 109.5 . . ? C18 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C18 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N6 C26 H26A 109.5 . . ? N6 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N6 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C29 103.2(4) . . ? C28 C27 H27A 111.1 . . ? C29 C27 H27A 111.1 . . ? C28 C27 H27B 111.1 . . ? C29 C27 H27B 111.1 . . ? H27A C27 H27B 109.1 . . ? C28 C28 C27 116.1(6) 2_655 . ? C28 C28 H28A 108.3 2_655 . ? C27 C28 H28A 108.3 . . ? C28 C28 H28B 108.3 2_655 . ? C27 C28 H28B 108.3 . . ? H28A C28 H28B 107.4 . . ? C29 C29 C27 121.5(3) 2_655 . ? C29 C29 H29A 107.0 2_655 . ? C27 C29 H29A 107.0 . . ? C29 C29 H29B 107.0 2_655 . ? C27 C29 H29B 107.0 . . ? H29A C29 H29B 106.7 . . ? C1 N3 C4 112.52(18) . . ? C1 N3 C16 125.02(19) . . ? C4 N3 C16 122.47(19) . . ? C1 N4 C3 111.38(19) . . ? C1 N4 C7 125.90(18) . . ? C3 N4 C7 122.71(19) . . ? C2 N5 C5 111.66(19) . . ? C2 N5 C17 125.41(18) . . ? C5 N5 C17 122.31(18) . . ? C2 N6 C6 111.61(18) . . ? C2 N6 C26 125.21(18) . . ? C6 N6 C26 122.94(18) . . ? 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 N2 Fe1 N1 O1 -13.2(17) . . . . ? C2 Fe1 N1 O1 114.5(17) . . . . ? C1 Fe1 N1 O1 -143.1(17) . . . . ? N1 Fe1 N2 O2 -1.6(11) . . . . ? C2 Fe1 N2 O2 -127.4(11) . . . . ? C1 Fe1 N2 O2 128.5(11) . . . . ? N2 Fe1 C1 N3 -134.23(19) . . . . ? N1 Fe1 C1 N3 -0.4(2) . . . . ? C2 Fe1 C1 N3 110.6(2) . . . . ? N2 Fe1 C1 N4 43.8(2) . . . . ? N1 Fe1 C1 N4 177.63(18) . . . . ? C2 Fe1 C1 N4 -71.4(2) . . . . ? N2 Fe1 C2 N6 -8.6(2) . . . . ? N1 Fe1 C2 N6 -140.16(19) . . . . ? C1 Fe1 C2 N6 105.9(2) . . . . ? N2 Fe1 C2 N5 169.12(18) . . . . ? N1 Fe1 C2 N5 37.5(2) . . . . ? C1 Fe1 C2 N5 -76.4(2) . . . . ? N4 C3 C4 N3 0.4(3) . . . . ? N5 C5 C6 N6 0.3(3) . . . . ? C12 C7 C8 C9 -3.0(3) . . . . ? N4 C7 C8 C9 179.43(19) . . . . ? C12 C7 C8 C14 175.9(2) . . . . ? N4 C7 C8 C14 -1.6(3) . . . . ? C7 C8 C9 C10 1.0(3) . . . . ? C14 C8 C9 C10 -178.0(2) . . . . ? C8 C9 C10 C11 1.6(4) . . . . ? C8 C9 C10 C15 -177.7(2) . . . . ? C9 C10 C11 C12 -2.3(4) . . . . ? C15 C10 C11 C12 177.0(2) . . . . ? C8 C7 C12 C11 2.4(3) . . . . ? N4 C7 C12 C11 180.0(2) . . . . ? C8 C7 C12 C13 -177.6(2) . . . . ? N4 C7 C12 C13 0.0(3) . . . . ? C10 C11 C12 C7 0.3(4) . . . . ? C10 C11 C12 C13 -179.7(2) . . . . ? C22 C17 C18 C19 2.1(3) . . . . ? N5 C17 C18 C19 179.04(19) . . . . ? C22 C17 C18 C24 -176.9(2) . . . . ? N5 C17 C18 C24 0.0(3) . . . . ? C17 C18 C19 C20 -0.2(3) . . . . ? C24 C18 C19 C20 178.8(2) . . . . ? C18 C19 C20 C21 -1.5(3) . . . . ? C18 C19 C20 C25 179.6(2) . . . . ? C19 C20 C21 C22 1.4(3) . . . . ? C25 C20 C21 C22 -179.7(2) . . . . ? C20 C21 C22 C17 0.4(3) . . . . ? C20 C21 C22 C23 -179.1(2) . . . . ? C18 C17 C22 C21 -2.2(3) . . . . ? N5 C17 C22 C21 -179.20(19) . . . . ? C18 C17 C22 C23 177.2(2) . . . . ? N5 C17 C22 C23 0.3(3) . . . . ? C29 C27 C28 C28 53.0(8) . . . 2_655 ? C28 C27 C29 C29 -23.9(11) . . . 2_655 ? N4 C1 N3 C4 0.2(2) . . . . ? Fe1 C1 N3 C4 178.58(18) . . . . ? N4 C1 N3 C16 -179.6(2) . . . . ? Fe1 C1 N3 C16 -1.2(3) . . . . ? C3 C4 N3 C1 -0.4(3) . . . . ? C3 C4 N3 C16 179.4(2) . . . . ? N3 C1 N4 C3 0.1(2) . . . . ? Fe1 C1 N4 C3 -178.32(17) . . . . ? N3 C1 N4 C7 179.9(2) . . . . ? Fe1 C1 N4 C7 1.5(3) . . . . ? C4 C3 N4 C1 -0.3(3) . . . . ? C4 C3 N4 C7 179.8(2) . . . . ? C12 C7 N4 C1 99.6(3) . . . . ? C8 C7 N4 C1 -82.8(3) . . . . ? C12 C7 N4 C3 -80.6(3) . . . . ? C8 C7 N4 C3 97.0(3) . . . . ? N6 C2 N5 C5 0.5(2) . . . . ? Fe1 C2 N5 C5 -177.70(16) . . . . ? N6 C2 N5 C17 171.5(2) . . . . ? Fe1 C2 N5 C17 -6.7(3) . . . . ? C6 C5 N5 C2 -0.5(3) . . . . ? C6 C5 N5 C17 -171.9(2) . . . . ? C18 C17 N5 C2 102.1(3) . . . . ? C22 C17 N5 C2 -80.9(3) . . . . ? C18 C17 N5 C5 -87.8(3) . . . . ? C22 C17 N5 C5 89.3(3) . . . . ? N5 C2 N6 C6 -0.3(2) . . . . ? Fe1 C2 N6 C6 177.86(16) . . . . ? N5 C2 N6 C26 -174.7(2) . . . . ? Fe1 C2 N6 C26 3.4(3) . . . . ? C5 C6 N6 C2 0.0(3) . . . . ? C5 C6 N6 C26 174.6(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.458 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.046 _vrf_PLAT413_datax ; Problem: A Short Inter XH3 .. XHn H25B .. H27A .. 1.67 Ang. RESPONSE: Distances between H atom on a (disordered?) cyclohexane to the a H atom on the complex. Distance is not accurately determined. ; # end Validation Reply Form _vrf_PLAT411_datax ; Problem: Short Inter H...H Contact H3 .. H27B .. 1.83 Ang. RESPONSE: Distances between H atom on a (disordered?) cyclohexane to the a H atom on the complex. Distance is not accurately determined. ; # end Validation Reply Form _vrf_PLAT360_datax ; Problem: Short C(sp3)-C(sp3) Bond C28 - C28_a ... 1.32 Ang. RESPONSE: Possibly disordered cyclohexane disorder was not modeled. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 948617' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_memestnic_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 B F4 Fe N5 O3' _chemical_formula_weight 432.97 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' F F 0.0171 0.0103 '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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.9146(13) _cell_length_b 15.4743(18) _cell_length_c 11.7202(14) _cell_angle_alpha 90.00 _cell_angle_beta 114.9070(10) _cell_angle_gamma 90.00 _cell_volume 1795.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.904 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9150 _exptl_absorpt_correction_T_max 0.9821 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21411 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4451 _reflns_number_gt 3944 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _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^)+(0.0462P)^2^+2.1586P] 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 4451 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _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 0.01648(3) 0.186084(18) 0.56245(2) 0.02027(9) Uani 1 1 d . . . N1 N -0.11643(18) 0.18432(12) 0.42100(17) 0.0283(4) Uani 1 1 d . . . N2 N -0.01005(18) 0.24434(12) 0.67313(17) 0.0275(4) Uani 1 1 d . . . N3 N 0.07709(17) 0.08507(12) 0.61177(17) 0.0263(4) Uani 1 1 d . . . O1 O -0.21132(19) 0.17777(13) 0.32755(17) 0.0455(5) Uani 1 1 d . . . O2 O -0.0399(2) 0.27870(13) 0.74412(17) 0.0445(4) Uani 1 1 d . . . O3 O 0.10228(18) 0.01390(10) 0.63907(17) 0.0385(4) Uani 1 1 d . . . C1 C 0.15792(18) 0.24918(12) 0.52808(17) 0.0191(3) Uani 1 1 d . . . N4 N 0.17537(16) 0.33536(10) 0.52355(15) 0.0209(3) Uani 1 1 d . . . N5 N 0.25254(16) 0.21325(10) 0.49622(15) 0.0195(3) Uani 1 1 d . . . C2 C 0.0963(2) 0.40222(13) 0.5508(2) 0.0272(4) Uani 1 1 d . . . H2A H 0.1268 0.4076 0.6402 0.041 Uiso 1 1 calc R . . H2B H 0.0025 0.3864 0.5135 0.041 Uiso 1 1 calc R . . H2C H 0.1077 0.4564 0.5166 0.041 Uiso 1 1 calc R . . C3 C 0.2795(2) 0.35346(13) 0.48935(19) 0.0247(4) Uani 1 1 d . . . H3 H 0.3101 0.4080 0.4802 0.030 Uiso 1 1 calc R . . C4 C 0.3280(2) 0.27698(13) 0.47194(19) 0.0237(4) Uani 1 1 d . . . H4 H 0.3984 0.2685 0.4482 0.028 Uiso 1 1 calc R . . C5 C 0.26953(18) 0.12200(12) 0.48176(17) 0.0189(3) Uani 1 1 d . . . C6 C 0.19820(19) 0.08475(13) 0.36360(18) 0.0223(4) Uani 1 1 d . . . C7 C 0.2191(2) -0.00291(13) 0.3503(2) 0.0254(4) Uani 1 1 d . . . H7 H 0.1720 -0.0293 0.2726 0.031 Uiso 1 1 calc R . . C8 C 0.3085(2) -0.05174(13) 0.4498(2) 0.0250(4) Uani 1 1 d . . . C9 C 0.3771(2) -0.01226(13) 0.5659(2) 0.0257(4) Uani 1 1 d . . . H9 H 0.4367 -0.0449 0.6329 0.031 Uiso 1 1 calc R . . C10 C 0.35927(18) 0.07477(13) 0.58495(18) 0.0216(4) Uani 1 1 d . . . C11 C 0.4324(2) 0.11564(15) 0.71275(19) 0.0304(4) Uani 1 1 d . . . H11A H 0.3719 0.1206 0.7528 0.046 Uiso 1 1 calc R . . H11B H 0.4636 0.1721 0.7035 0.046 Uiso 1 1 calc R . . H11C H 0.5082 0.0803 0.7634 0.046 Uiso 1 1 calc R . . C12 C 0.1023(2) 0.13634(15) 0.25325(19) 0.0313(5) Uani 1 1 d . . . H12A H 0.1526 0.1766 0.2273 0.047 Uiso 1 1 calc R . . H12B H 0.0406 0.1673 0.2772 0.047 Uiso 1 1 calc R . . H12C H 0.0527 0.0980 0.1849 0.047 Uiso 1 1 calc R . . C13 C 0.3339(2) -0.14546(14) 0.4312(3) 0.0355(5) Uani 1 1 d . . . H13A H 0.2804 -0.1616 0.3453 0.053 Uiso 1 1 calc R . . H13B H 0.3097 -0.1809 0.4857 0.053 Uiso 1 1 calc R . . H13C H 0.4279 -0.1535 0.4506 0.053 Uiso 1 1 calc R . . B1 B 0.1873(2) 0.10510(15) 0.9530(2) 0.0267(4) Uani 1 1 d . . . F1 F 0.0917(3) 0.15746(18) 0.9588(3) 0.0961(9) Uani 1 1 d . . . F2 F 0.1248(3) 0.03493(12) 0.8826(2) 0.0933(9) Uani 1 1 d . . . F3 F 0.25350(19) 0.14635(18) 0.8917(2) 0.0813(7) Uani 1 1 d . . . F4 F 0.27776(18) 0.07641(14) 1.06969(15) 0.0600(5) 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 0.01624(14) 0.02477(15) 0.01957(15) -0.00214(10) 0.00730(11) -0.00225(10) N1 0.0234(8) 0.0335(9) 0.0255(9) -0.0011(7) 0.0079(7) -0.0060(7) N2 0.0249(8) 0.0334(9) 0.0255(8) -0.0022(7) 0.0119(7) -0.0003(7) N3 0.0249(8) 0.0276(9) 0.0272(8) -0.0019(7) 0.0118(7) -0.0045(7) O1 0.0349(9) 0.0536(11) 0.0301(9) -0.0017(8) -0.0039(7) -0.0056(8) O2 0.0520(11) 0.0521(11) 0.0387(9) -0.0089(8) 0.0282(9) 0.0032(9) O3 0.0446(10) 0.0252(8) 0.0473(10) 0.0027(7) 0.0210(8) -0.0010(7) C1 0.0162(8) 0.0208(9) 0.0184(8) -0.0009(6) 0.0054(7) 0.0008(6) N4 0.0185(7) 0.0186(7) 0.0227(8) -0.0021(6) 0.0060(6) 0.0011(6) N5 0.0179(7) 0.0188(7) 0.0227(8) -0.0008(6) 0.0094(6) -0.0006(6) C2 0.0266(10) 0.0214(9) 0.0306(10) -0.0028(8) 0.0091(8) 0.0060(8) C3 0.0214(9) 0.0215(9) 0.0294(10) 0.0017(7) 0.0090(8) -0.0026(7) C4 0.0204(9) 0.0235(9) 0.0290(10) 0.0014(7) 0.0120(8) -0.0028(7) C5 0.0175(8) 0.0184(8) 0.0229(9) -0.0001(7) 0.0107(7) 0.0010(6) C6 0.0200(9) 0.0247(9) 0.0228(9) -0.0003(7) 0.0095(7) 0.0014(7) C7 0.0234(9) 0.0260(10) 0.0283(10) -0.0062(8) 0.0122(8) -0.0018(7) C8 0.0209(9) 0.0201(9) 0.0398(11) -0.0007(8) 0.0185(8) 0.0012(7) C9 0.0198(9) 0.0255(9) 0.0337(11) 0.0072(8) 0.0131(8) 0.0050(7) C10 0.0168(8) 0.0251(9) 0.0241(9) 0.0012(7) 0.0099(7) -0.0005(7) C11 0.0262(10) 0.0390(12) 0.0214(9) 0.0002(8) 0.0054(8) 0.0015(9) C12 0.0330(11) 0.0334(11) 0.0221(10) 0.0010(8) 0.0064(8) 0.0066(9) C13 0.0318(11) 0.0218(10) 0.0607(16) -0.0026(10) 0.0272(11) 0.0022(8) B1 0.0265(11) 0.0250(11) 0.0298(11) 0.0006(9) 0.0131(9) 0.0014(9) F1 0.1084(19) 0.1018(18) 0.1062(19) 0.0327(15) 0.0726(17) 0.0713(16) F2 0.124(2) 0.0389(10) 0.0651(13) -0.0005(9) -0.0108(13) -0.0201(11) F3 0.0457(10) 0.135(2) 0.0666(13) 0.0286(13) 0.0268(10) -0.0209(12) F4 0.0550(10) 0.0836(13) 0.0317(8) 0.0046(8) 0.0086(7) 0.0108(9) _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 N1 1.6816(18) . ? Fe1 N3 1.7008(18) . ? Fe1 N2 1.7017(18) . ? Fe1 C1 2.0057(19) . ? N1 O1 1.152(2) . ? N2 O2 1.145(2) . ? N3 O3 1.148(2) . ? C1 N4 1.351(2) . ? C1 N5 1.356(2) . ? N4 C3 1.384(3) . ? N4 C2 1.466(2) . ? N5 C4 1.389(2) . ? N5 C5 1.443(2) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.346(3) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 C6 1.396(3) . ? C5 C10 1.399(3) . ? C6 C7 1.395(3) . ? C6 C12 1.505(3) . ? C7 C8 1.388(3) . ? C7 H7 0.9300 . ? C8 C9 1.388(3) . ? C8 C13 1.510(3) . ? C9 C10 1.392(3) . ? C9 H9 0.9300 . ? C10 C11 1.508(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? B1 F1 1.345(3) . ? B1 F2 1.361(3) . ? B1 F3 1.372(3) . ? B1 F4 1.380(3) . ? 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 N1 Fe1 N3 111.76(9) . . ? N1 Fe1 N2 114.02(9) . . ? N3 Fe1 N2 113.23(9) . . ? N1 Fe1 C1 103.14(8) . . ? N3 Fe1 C1 107.07(8) . . ? N2 Fe1 C1 106.72(8) . . ? O1 N1 Fe1 174.63(18) . . ? O2 N2 Fe1 172.91(18) . . ? O3 N3 Fe1 171.89(17) . . ? N4 C1 N5 104.92(16) . . ? N4 C1 Fe1 128.42(13) . . ? N5 C1 Fe1 126.54(14) . . ? C1 N4 C3 110.95(16) . . ? C1 N4 C2 125.59(17) . . ? C3 N4 C2 123.45(17) . . ? C1 N5 C4 110.56(16) . . ? C1 N5 C5 125.71(16) . . ? C4 N5 C5 123.65(15) . . ? N4 C2 H2A 109.5 . . ? N4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 N4 106.81(17) . . ? C4 C3 H3 126.6 . . ? N4 C3 H3 126.6 . . ? C3 C4 N5 106.76(17) . . ? C3 C4 H4 126.6 . . ? N5 C4 H4 126.6 . . ? C6 C5 C10 122.46(18) . . ? C6 C5 N5 118.36(16) . . ? C10 C5 N5 119.16(17) . . ? C7 C6 C5 117.62(18) . . ? C7 C6 C12 120.45(18) . . ? C5 C6 C12 121.93(18) . . ? C8 C7 C6 121.70(19) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C9 C8 C7 118.84(18) . . ? C9 C8 C13 120.6(2) . . ? C7 C8 C13 120.5(2) . . ? C8 C9 C10 121.94(19) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C9 C10 C5 117.43(18) . . ? C9 C10 C11 120.93(18) . . ? C5 C10 C11 121.63(18) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? F1 B1 F2 108.0(3) . . ? F1 B1 F3 109.7(2) . . ? F2 B1 F3 107.1(2) . . ? F1 B1 F4 113.0(2) . . ? F2 B1 F4 108.1(2) . . ? F3 B1 F4 110.7(2) . . ? 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 N3 Fe1 N1 O1 45(2) . . . . ? N2 Fe1 N1 O1 -85(2) . . . . ? C1 Fe1 N1 O1 160(2) . . . . ? N1 Fe1 N2 O2 50.8(16) . . . . ? N3 Fe1 N2 O2 -78.5(15) . . . . ? C1 Fe1 N2 O2 163.9(15) . . . . ? N1 Fe1 N3 O3 -39.0(12) . . . . ? N2 Fe1 N3 O3 91.4(12) . . . . ? C1 Fe1 N3 O3 -151.3(12) . . . . ? N1 Fe1 C1 N4 83.48(18) . . . . ? N3 Fe1 C1 N4 -158.49(16) . . . . ? N2 Fe1 C1 N4 -36.95(19) . . . . ? N1 Fe1 C1 N5 -92.00(17) . . . . ? N3 Fe1 C1 N5 26.03(18) . . . . ? N2 Fe1 C1 N5 147.57(16) . . . . ? N5 C1 N4 C3 0.0(2) . . . . ? Fe1 C1 N4 C3 -176.26(14) . . . . ? N5 C1 N4 C2 -179.96(17) . . . . ? Fe1 C1 N4 C2 3.8(3) . . . . ? N4 C1 N5 C4 -0.1(2) . . . . ? Fe1 C1 N5 C4 176.26(14) . . . . ? N4 C1 N5 C5 -176.73(16) . . . . ? Fe1 C1 N5 C5 -0.4(3) . . . . ? C1 N4 C3 C4 0.1(2) . . . . ? C2 N4 C3 C4 -179.94(18) . . . . ? N4 C3 C4 N5 -0.1(2) . . . . ? C1 N5 C4 C3 0.1(2) . . . . ? C5 N5 C4 C3 176.88(17) . . . . ? C1 N5 C5 C6 89.5(2) . . . . ? C4 N5 C5 C6 -86.7(2) . . . . ? C1 N5 C5 C10 -92.3(2) . . . . ? C4 N5 C5 C10 91.4(2) . . . . ? C10 C5 C6 C7 -0.1(3) . . . . ? N5 C5 C6 C7 177.96(16) . . . . ? C10 C5 C6 C12 -179.77(18) . . . . ? N5 C5 C6 C12 -1.7(3) . . . . ? C5 C6 C7 C8 -0.7(3) . . . . ? C12 C6 C7 C8 178.95(19) . . . . ? C6 C7 C8 C9 0.9(3) . . . . ? C6 C7 C8 C13 -177.19(18) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? C13 C8 C9 C10 177.79(18) . . . . ? C8 C9 C10 C5 -0.5(3) . . . . ? C8 C9 C10 C11 178.48(18) . . . . ? C6 C5 C10 C9 0.7(3) . . . . ? N5 C5 C10 C9 -177.39(16) . . . . ? C6 C5 C10 C11 -178.24(18) . . . . ? N5 C5 C10 C11 3.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.906 _refine_diff_density_min -0.623 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 948618'