# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- Rev_1_1.cif' _publ_contact_author ; Xuetai Chen, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, China ; _publ_contact_author_email xtchen@nju.edu.cn _publ_contact_author_name 'Xuetai Chen,' _publ_author_name 'Xuetai Chen' # Attachment '- Rev_1_3.cif' data_1_3 _database_code_depnum_ccdc_archive 'CCDC 869060' #TrackingRef '- Rev_1_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H39 Co2 I2 N25 O4' _chemical_formula_weight 1137.48 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.9487(18) _cell_length_b 12.1594(13) _cell_length_c 20.182(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.802(3) _cell_angle_gamma 90.00 _cell_volume 4661.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2248 _exptl_absorpt_coefficient_mu 2.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6223 _exptl_absorpt_correction_T_max 0.7723 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 12844 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4260 _reflns_number_gt 3577 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0500P)^2^+1.9900P] 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 4260 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8427(2) 0.5730(3) 0.6470(2) 0.0398(8) Uani 1 1 d . . . C2 C 0.8685(2) 0.7106(3) 0.7215(2) 0.0437(8) Uani 1 1 d . . . H2 H 0.8773 0.7820 0.7384 0.052 Uiso 1 1 d R . . C3 C 0.83431(18) 0.7362(3) 0.54091(19) 0.0359(7) Uani 1 1 d . . . H3 H 0.8297 0.7925 0.5086 0.043 Uiso 1 1 d R . . C4 C 0.7918(2) 0.5235(3) 0.4204(2) 0.0387(8) Uani 1 1 d . . . H4 H 0.7797 0.5094 0.3729 0.046 Uiso 1 1 d R . . C5 C 0.82217(19) 0.7114(3) 0.39832(19) 0.0371(7) Uani 1 1 d . . . H5A H 0.8187 0.6820 0.3532 0.056 Uiso 1 1 d R . . H5B H 0.8674 0.7455 0.4177 0.056 Uiso 1 1 d R . . H5C H 0.7858 0.7651 0.3940 0.056 Uiso 1 1 d R . . C6 C 0.8530(2) 0.4260(3) 0.7387(2) 0.0438(8) Uani 1 1 d . . . H6A H 0.8156 0.3863 0.7062 0.066 Uiso 1 1 calc R . . H6B H 0.8437 0.4311 0.7825 0.066 Uiso 1 1 calc R . . H6C H 0.8967 0.3880 0.7450 0.066 Uiso 1 1 calc R . . C7 C 0.9062(2) 0.4425(3) 0.5731(2) 0.0445(9) Uani 1 1 d . . . C8 C 0.9865(2) 0.3147(3) 0.5853(2) 0.0480(9) Uani 1 1 d . . . H8 H 1.0066 0.2452 0.5877 0.058 Uiso 1 1 calc R . . C9 C 0.8123(2) 0.2680(3) 0.5800(2) 0.0425(8) Uani 1 1 d . . . H9 H 0.7833 0.2088 0.5816 0.051 Uiso 1 1 calc R . . C10 C 0.6856(2) 0.4659(3) 0.5696(2) 0.0444(9) Uani 1 1 d . . . H10 H 0.6398 0.4770 0.5707 0.053 Uiso 1 1 calc R . . C11 C 0.6857(2) 0.2848(3) 0.6181(2) 0.0441(9) Uani 1 1 d . . . H11A H 0.6373 0.3018 0.6126 0.066 Uiso 1 1 calc R . . H11B H 0.7106 0.2753 0.6666 0.066 Uiso 1 1 calc R . . H11C H 0.6883 0.2183 0.5934 0.066 Uiso 1 1 calc R . . C12 C 0.9918(2) 0.6015(3) 0.5873(2) 0.0494(10) Uani 1 1 d . . . H12A H 1.0414 0.6059 0.5935 0.074 Uiso 1 1 calc R . . H12B H 0.9818 0.6358 0.6261 0.074 Uiso 1 1 calc R . . H12C H 0.9663 0.6387 0.5451 0.074 Uiso 1 1 calc R . . C13 C 0.4760(5) 0.4731(7) 0.5815(5) 0.0481(18) Uani 0.50 1 d P . . H13A H 0.4544 0.5236 0.5446 0.072 Uiso 0.50 1 calc PR . . H13B H 0.4482 0.4073 0.5757 0.072 Uiso 0.50 1 calc PR . . H13C H 0.5225 0.4551 0.5802 0.072 Uiso 0.50 1 calc PR . . C14 C 0.4805(5) 0.5229(8) 0.6473(5) 0.0513(19) Uani 0.50 1 d P . . Co1 Co 0.81587(3) 0.50226(3) 0.55895(2) 0.03450(16) Uani 1 1 d . . . I1 I 0.663130(15) 0.56422(2) 0.735906(16) 0.05119(11) Uani 1 1 d . . . N1 N 0.85768(18) 0.5366(3) 0.71187(18) 0.0449(7) Uani 1 1 d . . . N2 N 0.87051(18) 0.6250(3) 0.76004(17) 0.0444(7) Uani 1 1 d . . . N3 N 0.85231(16) 0.6829(3) 0.65322(16) 0.0395(7) Uani 1 1 d . . . N4 N 0.84465(16) 0.7676(2) 0.60444(16) 0.0386(7) Uani 1 1 d . . . N5 N 0.82942(16) 0.6352(2) 0.51575(16) 0.0367(6) Uani 1 1 d . . . N6 N 0.81386(16) 0.6224(2) 0.44372(16) 0.0369(6) Uani 1 1 d . . . N7 N 0.97006(19) 0.4854(3) 0.5830(2) 0.0469(8) Uani 1 1 d . . . N8 N 1.02082(18) 0.4063(3) 0.5902(2) 0.0478(8) Uani 1 1 d . . . N9 N 0.91832(17) 0.3339(3) 0.57641(18) 0.0450(7) Uani 1 1 d . . . N10 N 0.87157(18) 0.2448(3) 0.57143(19) 0.0464(8) Uani 1 1 d . . . N11 N 0.78758(17) 0.3671(2) 0.58672(18) 0.0411(7) Uani 1 1 d . . . N12 N 0.71672(17) 0.3729(2) 0.59080(18) 0.0408(7) Uani 1 1 d . . . N13 N 0.4836(4) 0.5648(6) 0.7027(4) 0.0499(16) Uani 0.50 1 d P . . O1 O 0.71751(14) 0.5434(2) 0.54675(15) 0.0422(6) Uani 1 1 d . . . O2 O 0.78688(13) 0.44809(19) 0.46109(14) 0.0370(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 C1 0.0467(19) 0.0409(19) 0.031(2) -0.0003(15) 0.0112(15) -0.0003(15) C2 0.046(2) 0.0466(19) 0.035(2) -0.0003(15) 0.0081(16) 0.0009(15) C3 0.0380(17) 0.0347(17) 0.0350(19) -0.0021(14) 0.0111(15) -0.0034(13) C4 0.046(2) 0.0388(16) 0.0301(19) 0.0004(16) 0.0088(15) 0.0001(16) C5 0.0423(18) 0.0369(17) 0.0347(19) 0.0053(14) 0.0158(15) 0.0034(14) C6 0.0447(19) 0.048(2) 0.036(2) 0.0031(16) 0.0077(16) -0.0045(16) C7 0.0431(19) 0.0399(18) 0.050(2) 0.0047(16) 0.0135(17) 0.0027(16) C8 0.046(2) 0.042(2) 0.057(2) 0.0030(18) 0.0160(18) 0.0069(16) C9 0.046(2) 0.0332(18) 0.049(2) 0.0065(16) 0.0142(17) 0.0045(15) C10 0.046(2) 0.0371(19) 0.052(2) 0.0053(17) 0.0183(18) 0.0044(16) C11 0.047(2) 0.0369(18) 0.052(2) 0.0075(16) 0.0202(18) 0.0028(15) C12 0.044(2) 0.042(2) 0.058(3) 0.0085(18) 0.0090(18) 0.0039(16) C13 0.050(5) 0.042(4) 0.050(5) 0.006(4) 0.012(4) 0.001(4) C14 0.043(4) 0.052(4) 0.059(6) 0.004(4) 0.016(4) 0.007(4) Co1 0.0389(3) 0.0325(3) 0.0302(3) 0.00326(16) 0.0078(3) 0.00183(16) I1 0.05022(16) 0.04200(15) 0.0586(2) 0.00440(11) 0.01262(12) 0.00509(11) N1 0.0521(19) 0.0427(18) 0.0371(18) 0.0002(14) 0.0093(14) -0.0036(14) N2 0.0500(17) 0.0459(18) 0.0335(17) -0.0003(13) 0.0073(13) -0.0007(14) N3 0.0431(16) 0.0416(16) 0.0325(16) -0.0005(13) 0.0097(12) -0.0007(12) N4 0.0435(16) 0.0403(16) 0.0327(16) -0.0004(12) 0.0128(13) 0.0004(12) N5 0.0458(15) 0.0346(14) 0.0316(15) 0.0031(12) 0.0145(12) 0.0005(12) N6 0.0480(16) 0.0348(15) 0.0293(15) 0.0007(11) 0.0138(12) -0.0007(12) N7 0.0411(19) 0.0410(16) 0.058(2) 0.0078(15) 0.0139(17) 0.0044(13) N8 0.0408(17) 0.0449(17) 0.058(2) 0.0042(15) 0.0160(16) 0.0050(14) N9 0.0430(16) 0.0408(16) 0.0504(19) 0.0062(14) 0.0131(14) 0.0053(13) N10 0.0477(18) 0.0378(15) 0.057(2) 0.0065(14) 0.0201(16) 0.0030(13) N11 0.0445(16) 0.0331(14) 0.0486(18) 0.0078(13) 0.0185(14) 0.0059(13) N12 0.0451(16) 0.0346(15) 0.0457(19) 0.0071(13) 0.0185(14) 0.0042(13) N13 0.042(3) 0.046(3) 0.063(5) 0.010(3) 0.018(3) 0.007(3) O1 0.0468(14) 0.0330(14) 0.0489(16) 0.0076(10) 0.0176(12) 0.0071(10) O2 0.0416(13) 0.0345(12) 0.0369(14) 0.0008(10) 0.0146(11) -0.0012(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 C1 N1 1.326(5) . ? C1 N3 1.350(5) . ? C1 Co1 1.899(4) . ? C2 N2 1.293(5) . ? C2 N3 1.358(5) . ? C2 H2 0.9300 . ? C3 N4 1.292(5) . ? C3 N5 1.321(5) . ? C3 H3 0.9300 . ? C4 O2 1.255(5) . ? C4 N6 1.317(5) . ? C4 H4 0.9300 . ? C5 N6 1.460(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N1 1.463(5) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N7 1.333(6) . ? C7 N9 1.340(5) . ? C7 Co1 1.883(4) . ? C8 N8 1.295(5) . ? C8 N9 1.338(5) . ? C8 H8 0.9300 . ? C9 N10 1.278(5) . ? C9 N11 1.325(5) . ? C9 H9 0.9300 . ? C10 N12 1.298(5) . ? C10 O1 1.299(5) . ? C10 H10 0.9300 . ? C11 N12 1.430(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N7 1.472(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.437(13) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N13 1.214(12) . ? Co1 N11 1.878(3) . ? Co1 N5 1.894(3) . ? Co1 O1 1.966(3) . ? Co1 O2 1.993(3) . ? N1 N2 1.420(5) . ? N3 N4 1.400(4) . ? N5 N6 1.399(4) . ? N7 N8 1.371(5) . ? N9 N10 1.413(5) . ? N11 N12 1.443(4) . ? N13 N13 1.820(17) 2_656 ? 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 C1 N3 104.9(3) . . ? N1 C1 Co1 133.3(3) . . ? N3 C1 Co1 121.8(3) . . ? N2 C2 N3 111.4(3) . . ? N2 C2 H2 124.3 . . ? N3 C2 H2 124.3 . . ? N4 C3 N5 128.8(3) . . ? N4 C3 H3 115.4 . . ? N5 C3 H3 115.8 . . ? O2 C4 N6 121.2(3) . . ? O2 C4 H4 119.4 . . ? N6 C4 H4 119.4 . . ? N6 C5 H5A 109.2 . . ? N6 C5 H5B 109.7 . . ? H5A C5 H5B 109.5 . . ? N6 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N7 C7 N9 103.2(3) . . ? N7 C7 Co1 134.2(3) . . ? N9 C7 Co1 122.5(3) . . ? N8 C8 N9 110.6(4) . . ? N8 C8 H8 124.7 . . ? N9 C8 H8 124.7 . . ? N10 C9 N11 127.1(4) . . ? N10 C9 H9 116.4 . . ? N11 C9 H9 116.4 . . ? N12 C10 O1 120.8(4) . . ? N12 C10 H10 119.6 . . ? O1 C10 H10 119.6 . . ? N12 C11 H11A 109.5 . . ? N12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N7 C12 H12A 109.5 . . ? N7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N13 C14 C13 179.4(9) . . ? N11 Co1 C7 88.73(15) . . ? N11 Co1 N5 169.12(14) . . ? C7 Co1 N5 97.73(15) . . ? N11 Co1 C1 98.14(16) . . ? C7 Co1 C1 92.86(18) . . ? N5 Co1 C1 90.30(15) . . ? N11 Co1 O1 83.15(12) . . ? C7 Co1 O1 171.83(14) . . ? N5 Co1 O1 90.14(12) . . ? C1 Co1 O1 89.26(14) . . ? N11 Co1 O2 89.08(13) . . ? C7 Co1 O2 89.82(15) . . ? N5 Co1 O2 82.23(11) . . ? C1 Co1 O2 172.34(13) . . ? O1 Co1 O2 89.08(11) . . ? C1 N1 N2 111.2(3) . . ? C1 N1 C6 130.7(3) . . ? N2 N1 C6 117.5(3) . . ? C2 N2 N1 103.4(3) . . ? C1 N3 C2 108.8(3) . . ? C1 N3 N4 132.9(3) . . ? C2 N3 N4 118.1(3) . . ? C3 N4 N3 115.5(3) . . ? C3 N5 N6 118.0(3) . . ? C3 N5 Co1 128.3(3) . . ? N6 N5 Co1 111.5(2) . . ? C4 N6 N5 114.6(3) . . ? C4 N6 C5 122.9(3) . . ? N5 N6 C5 122.6(3) . . ? C7 N7 N8 112.5(3) . . ? C7 N7 C12 129.4(3) . . ? N8 N7 C12 118.1(3) . . ? C8 N8 N7 103.8(3) . . ? C8 N9 C7 109.8(3) . . ? C8 N9 N10 119.9(3) . . ? C7 N9 N10 130.3(3) . . ? C9 N10 N9 116.0(3) . . ? C9 N11 N12 116.9(3) . . ? C9 N11 Co1 127.6(3) . . ? N12 N11 Co1 111.3(2) . . ? C10 N12 C11 124.0(3) . . ? C10 N12 N11 113.7(3) . . ? C11 N12 N11 122.2(3) . . ? C14 N13 N13 150.2(6) . 2_656 ? C10 O1 Co1 110.5(2) . . ? C4 O2 Co1 110.5(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 N7 C7 Co1 N11 -160.1(5) . . . . ? N9 C7 Co1 N11 18.6(4) . . . . ? N7 C7 Co1 N5 28.7(5) . . . . ? N9 C7 Co1 N5 -152.6(4) . . . . ? N7 C7 Co1 C1 -62.0(5) . . . . ? N9 C7 Co1 C1 116.7(4) . . . . ? N7 C7 Co1 O1 -166.9(8) . . . . ? N9 C7 Co1 O1 11.8(14) . . . . ? N7 C7 Co1 O2 110.9(5) . . . . ? N9 C7 Co1 O2 -70.5(4) . . . . ? N1 C1 Co1 N11 17.5(4) . . . . ? N3 C1 Co1 N11 -164.5(3) . . . . ? N1 C1 Co1 C7 -71.6(4) . . . . ? N3 C1 Co1 C7 106.4(3) . . . . ? N1 C1 Co1 N5 -169.4(4) . . . . ? N3 C1 Co1 N5 8.7(3) . . . . ? N1 C1 Co1 O1 100.5(4) . . . . ? N3 C1 Co1 O1 -81.5(3) . . . . ? N1 C1 Co1 O2 178.0(8) . . . . ? N3 C1 Co1 O2 -4.0(12) . . . . ? N3 C1 N1 N2 5.7(4) . . . . ? Co1 C1 N1 N2 -176.1(3) . . . . ? N3 C1 N1 C6 175.9(4) . . . . ? Co1 C1 N1 C6 -5.8(7) . . . . ? N3 C2 N2 N1 2.8(4) . . . . ? C1 N1 N2 C2 -5.4(4) . . . . ? C6 N1 N2 C2 -177.1(3) . . . . ? N1 C1 N3 C2 -3.8(4) . . . . ? Co1 C1 N3 C2 177.7(3) . . . . ? N1 C1 N3 N4 -179.4(3) . . . . ? Co1 C1 N3 N4 2.1(6) . . . . ? N2 C2 N3 C1 0.5(5) . . . . ? N2 C2 N3 N4 176.8(3) . . . . ? N5 C3 N4 N3 0.6(5) . . . . ? C1 N3 N4 C3 -9.5(6) . . . . ? C2 N3 N4 C3 175.2(3) . . . . ? N4 C3 N5 N6 176.3(3) . . . . ? N4 C3 N5 Co1 14.8(6) . . . . ? N11 Co1 N5 C3 124.2(7) . . . . ? C7 Co1 N5 C3 -109.7(3) . . . . ? C1 Co1 N5 C3 -16.8(3) . . . . ? O1 Co1 N5 C3 72.4(3) . . . . ? O2 Co1 N5 C3 161.5(3) . . . . ? N11 Co1 N5 N6 -38.3(8) . . . . ? C7 Co1 N5 N6 87.7(3) . . . . ? C1 Co1 N5 N6 -179.3(2) . . . . ? O1 Co1 N5 N6 -90.1(2) . . . . ? O2 Co1 N5 N6 -1.0(2) . . . . ? O2 C4 N6 N5 -1.1(5) . . . . ? O2 C4 N6 C5 178.3(3) . . . . ? C3 N5 N6 C4 -163.1(3) . . . . ? Co1 N5 N6 C4 1.4(4) . . . . ? C3 N5 N6 C5 17.5(5) . . . . ? Co1 N5 N6 C5 -177.9(2) . . . . ? N9 C7 N7 N8 1.9(5) . . . . ? Co1 C7 N7 N8 -179.3(3) . . . . ? N9 C7 N7 C12 -177.9(4) . . . . ? Co1 C7 N7 C12 1.0(8) . . . . ? N9 C8 N8 N7 -0.7(5) . . . . ? C7 N7 N8 C8 -0.8(5) . . . . ? C12 N7 N8 C8 179.0(4) . . . . ? N8 C8 N9 C7 1.9(5) . . . . ? N8 C8 N9 N10 -178.6(4) . . . . ? N7 C7 N9 C8 -2.3(5) . . . . ? Co1 C7 N9 C8 178.7(3) . . . . ? N7 C7 N9 N10 178.3(4) . . . . ? Co1 C7 N9 N10 -0.7(6) . . . . ? N11 C9 N10 N9 6.5(6) . . . . ? C8 N9 N10 C9 163.6(4) . . . . ? C7 N9 N10 C9 -17.0(6) . . . . ? N10 C9 N11 N12 175.6(4) . . . . ? N10 C9 N11 Co1 20.9(7) . . . . ? C7 Co1 N11 C9 -29.2(4) . . . . ? N5 Co1 N11 C9 97.5(7) . . . . ? C1 Co1 N11 C9 -121.9(4) . . . . ? O1 Co1 N11 C9 149.8(4) . . . . ? O2 Co1 N11 C9 60.6(4) . . . . ? C7 Co1 N11 N12 174.9(3) . . . . ? N5 Co1 N11 N12 -58.4(8) . . . . ? C1 Co1 N11 N12 82.1(3) . . . . ? O1 Co1 N11 N12 -6.1(3) . . . . ? O2 Co1 N11 N12 -95.3(3) . . . . ? O1 C10 N12 C11 178.5(4) . . . . ? O1 C10 N12 N11 0.5(6) . . . . ? C9 N11 N12 C10 -153.7(4) . . . . ? Co1 N11 N12 C10 5.1(4) . . . . ? C9 N11 N12 C11 28.3(5) . . . . ? Co1 N11 N12 C11 -173.0(3) . . . . ? C13 C14 N13 N13 121(91) . . . 2_656 ? N12 C10 O1 Co1 -5.5(5) . . . . ? N11 Co1 O1 C10 6.4(3) . . . . ? C7 Co1 O1 C10 13.3(12) . . . . ? N5 Co1 O1 C10 177.8(3) . . . . ? C1 Co1 O1 C10 -91.9(3) . . . . ? O2 Co1 O1 C10 95.6(3) . . . . ? N6 C4 O2 Co1 0.2(4) . . . . ? N11 Co1 O2 C4 173.9(3) . . . . ? C7 Co1 O2 C4 -97.3(3) . . . . ? N5 Co1 O2 C4 0.5(3) . . . . ? C1 Co1 O2 C4 13.3(11) . . . . ? O1 Co1 O2 C4 90.8(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.820 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.101 data_22 _database_code_depnum_ccdc_archive 'CCDC 869061' #TrackingRef '- Rev_1_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 Fe I N12 O3' _chemical_formula_weight 563.15 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.555(3) _cell_length_b 25.707(11) _cell_length_c 11.485(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.827(6) _cell_angle_gamma 90.00 _cell_volume 2225.7(16) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1116 _exptl_absorpt_coefficient_mu 2.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5905 _exptl_absorpt_correction_T_max 0.6547 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11327 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4215 _reflns_number_gt 3020 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0850P)^2^+1.9900P] 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 4215 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1498 _refine_ls_wR_factor_gt 0.1384 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2516(10) 0.0949(2) 0.3169(6) 0.0262(14) Uani 1 1 d . . . C2 C 0.0017(9) 0.0482(3) 0.3172(6) 0.0289(15) Uani 1 1 d . . . H2 H -0.0803 0.0235 0.3378 0.035 Uiso 1 1 calc R . . C3 C 0.3541(8) 0.0435(3) 0.5265(7) 0.0291(16) Uani 1 1 d . . . H3 H 0.3809 0.0265 0.5970 0.035 Uiso 1 1 calc R . . C4 C 0.7482(9) 0.1138(3) 0.5368(7) 0.0299(16) Uani 1 1 d . . . H4 H 0.8548 0.1174 0.5814 0.036 Uiso 1 1 calc R . . C5 C 0.1390(9) 0.1534(3) 0.1494(6) 0.0274(15) Uani 1 1 d . . . H5A H 0.2295 0.1777 0.1755 0.041 Uiso 1 1 calc R . . H5B H 0.0267 0.1709 0.1403 0.041 Uiso 1 1 calc R . . H5C H 0.1671 0.1389 0.0758 0.041 Uiso 1 1 calc R . . C6 C 0.6127(9) 0.0745(3) 0.7062(6) 0.0281(15) Uani 1 1 d . . . H6A H 0.7181 0.0874 0.7480 0.042 Uiso 1 1 calc R . . H6B H 0.6130 0.0372 0.7080 0.042 Uiso 1 1 calc R . . H6C H 0.5101 0.0873 0.7421 0.042 Uiso 1 1 calc R . . C7 C 0.4340(11) 0.1841(3) 0.3991(6) 0.0305(16) Uani 1 1 d . . . C8 C 0.4451(11) 0.2701(3) 0.3920(6) 0.0320(16) Uani 1 1 d . . . H8 H 0.4742 0.3034 0.3681 0.038 Uiso 1 1 calc R . . C9 C 0.6203(9) 0.1866(3) 0.1885(7) 0.0308(16) Uani 1 1 d . . . H9 H 0.6828 0.1890 0.1217 0.037 Uiso 1 1 calc R . . C10 C 0.5786(10) 0.0537(3) 0.1779(7) 0.0341(17) Uani 1 1 d . . . H10 H 0.5873 0.0249 0.1298 0.041 Uiso 1 1 calc R . . C11 C 0.2186(12) 0.1802(3) 0.5543(7) 0.0398(19) Uani 1 1 d . . . H11A H 0.1168 0.1661 0.5107 0.060 Uiso 1 1 calc R . . H11B H 0.1809 0.2053 0.6092 0.060 Uiso 1 1 calc R . . H11C H 0.2819 0.1527 0.5953 0.060 Uiso 1 1 calc R . . C12 C 0.6133(11) 0.1089(3) 0.0128(6) 0.0353(17) Uani 1 1 d . . . H12B H 0.7376 0.1049 0.0023 0.053 Uiso 1 1 calc R . . H12C H 0.5770 0.1436 -0.0081 0.053 Uiso 1 1 calc R . . H12A H 0.5472 0.0845 -0.0361 0.053 Uiso 1 1 calc R . . Fe1 Fe 0.49095(13) 0.11468(4) 0.35895(9) 0.0258(2) Uani 1 1 d . . . I1 I 0.61738(6) 0.412791(17) 0.32764(4) 0.02617(17) Uani 1 1 d . . . N1 N 0.1289(7) 0.1108(2) 0.2371(5) 0.0262(12) Uani 1 1 d . . . N2 N -0.0188(8) 0.0812(2) 0.2322(6) 0.0327(14) Uani 1 1 d . . . N3 N 0.1654(8) 0.0564(2) 0.3708(5) 0.0234(11) Uani 1 1 d . . . N4 N 0.2214(7) 0.0264(2) 0.4701(5) 0.0215(11) Uani 1 1 d . . . N5 N 0.4674(8) 0.0824(2) 0.5037(5) 0.0259(12) Uani 1 1 d . . . N6 N 0.6083(7) 0.0923(2) 0.5851(5) 0.0264(12) Uani 1 1 d . . . N7 N 0.3354(10) 0.2054(3) 0.4741(6) 0.0401(16) Uani 1 1 d . . . N8 N 0.3411(9) 0.2605(2) 0.4777(6) 0.0343(14) Uani 1 1 d . . . N9 N 0.5046(8) 0.2261(2) 0.3428(5) 0.0309(14) Uani 1 1 d . . . N10 N 0.6060(9) 0.2291(2) 0.2493(6) 0.0393(16) Uani 1 1 d . . . N11 N 0.5546(8) 0.1406(2) 0.2126(5) 0.0269(13) Uani 1 1 d . . . N12 N 0.5810(8) 0.0995(2) 0.1320(5) 0.0281(13) Uani 1 1 d . . . O1 O 0.7380(6) 0.12904(18) 0.4317(4) 0.0252(10) Uani 1 1 d . . . O2 O 0.5649(6) 0.04654(17) 0.2864(4) 0.0254(10) Uani 1 1 d . . . O1W O 0.105(3) 0.2714(7) 0.237(2) 0.058(6) Uani 0.30 1 d P . . H1X H 0.1244 0.2892 0.2986 0.069 Uiso 0.30 1 d PR . . H1Y H 0.1667 0.2833 0.1836 0.069 Uiso 0.30 1 d PR . . O2W O 0.948(3) 0.2530(9) 0.371(2) 0.063(6) Uani 0.30 1 d P . . H2X H 0.9930 0.2331 0.4241 0.076 Uiso 0.30 1 d PR . . H2Y H 0.8434 0.2429 0.3505 0.076 Uiso 0.30 1 d PR . . O3W O 0.2137(17) 0.0059(5) 0.0819(11) 0.033(3) Uani 0.40 1 d P . . H3X H 0.1046 -0.0012 0.0671 0.039 Uiso 0.40 1 d PR . . H3Y H 0.2554 0.0193 0.0218 0.039 Uiso 0.40 1 d PR . . 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 C1 0.034(4) 0.016(3) 0.028(4) 0.006(3) 0.001(3) -0.004(3) C2 0.032(4) 0.035(4) 0.022(4) -0.002(3) 0.011(3) -0.005(3) C3 0.019(3) 0.026(3) 0.043(4) -0.002(3) 0.007(3) -0.009(3) C4 0.023(3) 0.038(4) 0.029(4) -0.012(3) 0.005(3) 0.000(3) C5 0.030(3) 0.038(4) 0.015(3) -0.005(3) -0.001(3) -0.013(3) C6 0.022(3) 0.029(4) 0.033(4) -0.010(3) -0.003(3) -0.008(3) C7 0.049(4) 0.023(3) 0.020(3) 0.002(3) 0.013(3) 0.006(3) C8 0.058(5) 0.026(3) 0.014(3) 0.001(3) 0.016(3) -0.002(3) C9 0.029(4) 0.028(3) 0.038(4) 0.007(3) 0.015(3) 0.004(3) C10 0.039(4) 0.031(4) 0.031(4) 0.002(3) -0.001(3) -0.002(3) C11 0.049(5) 0.039(4) 0.033(4) -0.004(3) 0.013(4) 0.009(4) C12 0.051(5) 0.041(4) 0.015(3) 0.009(3) 0.008(3) -0.002(4) Fe1 0.0277(5) 0.0278(5) 0.0224(5) 0.0011(4) 0.0043(4) 0.0004(4) I1 0.0214(2) 0.0252(2) 0.0322(3) 0.00052(18) 0.00327(17) 0.00001(17) N1 0.018(3) 0.032(3) 0.029(3) -0.003(3) 0.006(2) 0.002(2) N2 0.029(3) 0.037(3) 0.032(3) -0.002(3) 0.000(3) -0.003(3) N3 0.028(3) 0.025(3) 0.017(3) 0.001(2) 0.006(2) -0.002(2) N4 0.019(3) 0.024(3) 0.021(3) -0.004(2) 0.001(2) -0.001(2) N5 0.027(3) 0.025(3) 0.027(3) -0.006(2) 0.010(2) -0.007(2) N6 0.019(3) 0.034(3) 0.027(3) 0.004(2) 0.012(2) 0.012(2) N7 0.059(4) 0.032(3) 0.030(4) -0.006(3) 0.013(3) 0.002(3) N8 0.046(4) 0.029(3) 0.029(3) 0.000(2) 0.011(3) -0.001(3) N9 0.039(3) 0.028(3) 0.028(3) 0.007(2) 0.025(3) 0.011(3) N10 0.047(4) 0.031(3) 0.044(4) 0.000(3) 0.030(3) 0.005(3) N11 0.035(3) 0.026(3) 0.021(3) 0.005(2) 0.010(2) 0.004(2) N12 0.033(3) 0.018(3) 0.033(3) 0.006(2) 0.005(3) 0.001(2) O1 0.019(2) 0.027(2) 0.032(3) 0.007(2) 0.0159(19) 0.0075(18) O2 0.023(2) 0.026(2) 0.029(3) 0.006(2) 0.012(2) -0.0011(19) O1W 0.043(11) 0.043(11) 0.086(16) -0.037(11) -0.004(11) 0.024(9) O2W 0.074(15) 0.045(11) 0.069(16) 0.013(11) -0.016(13) -0.015(11) O3W 0.032(6) 0.032(7) 0.033(7) 0.011(5) -0.003(5) -0.002(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 C1 N1 1.324(9) . ? C1 N3 1.355(8) . ? C1 Fe1 1.910(7) . ? C2 N2 1.293(9) . ? C2 N3 1.360(9) . ? C2 H2 0.9300 . ? C3 N4 1.237(9) . ? C3 N5 1.354(8) . ? C3 H3 0.9300 . ? C4 O1 1.267(9) . ? C4 N6 1.345(9) . ? C4 H4 0.9300 . ? C5 N1 1.493(9) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N6 1.462(9) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N7 1.296(9) . ? C7 N9 1.384(9) . ? C7 Fe1 1.900(7) . ? C8 N8 1.323(9) . ? C8 N9 1.354(9) . ? C8 H8 0.9300 . ? C9 N10 1.305(9) . ? C9 N11 1.319(9) . ? C9 H9 0.9300 . ? C10 O2 1.271(9) . ? C10 N12 1.289(9) . ? C10 H10 0.9300 . ? C11 N7 1.467(11) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N12 1.428(9) . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C12 H12A 0.9600 . ? Fe1 N5 1.877(6) . ? Fe1 N11 1.899(6) . ? Fe1 O1 2.027(5) . ? Fe1 O2 2.034(5) . ? N1 N2 1.350(8) . ? N3 N4 1.418(8) . ? N5 N6 1.392(8) . ? N7 N8 1.418(9) . ? N9 N10 1.362(8) . ? N11 N12 1.428(8) . ? O1W H1X 0.8500 . ? O1W H1Y 0.8500 . ? O2W H2X 0.8501 . ? O2W H2Y 0.8500 . ? O3W H3X 0.8500 . ? O3W H3Y 0.8501 . ? 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 C1 N3 101.9(6) . . ? N1 C1 Fe1 134.4(5) . . ? N3 C1 Fe1 123.7(5) . . ? N2 C2 N3 107.4(6) . . ? N2 C2 H2 126.3 . . ? N3 C2 H2 126.3 . . ? N4 C3 N5 131.4(8) . . ? N4 C3 H3 114.3 . . ? N5 C3 H3 114.3 . . ? O1 C4 N6 121.4(6) . . ? O1 C4 H4 119.3 . . ? N6 C4 H4 119.3 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N6 C6 H6A 109.5 . . ? N6 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N6 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N7 C7 N9 103.8(6) . . ? N7 C7 Fe1 135.0(6) . . ? N9 C7 Fe1 121.2(5) . . ? N8 C8 N9 112.6(6) . . ? N8 C8 H8 123.7 . . ? N9 C8 H8 123.7 . . ? N10 C9 N11 126.4(7) . . ? N10 C9 H9 116.8 . . ? N11 C9 H9 116.8 . . ? O2 C10 N12 122.5(7) . . ? O2 C10 H10 118.7 . . ? N12 C10 H10 118.7 . . ? N7 C11 H11A 109.5 . . ? N7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N12 C12 H12B 109.5 . . ? N12 C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N12 C12 H12A 109.5 . . ? H12B C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? N5 Fe1 N11 169.5(3) . . ? N5 Fe1 C7 99.4(3) . . ? N11 Fe1 C7 87.7(3) . . ? N5 Fe1 C1 87.8(3) . . ? N11 Fe1 C1 99.3(3) . . ? C7 Fe1 C1 94.9(3) . . ? N5 Fe1 O1 81.6(2) . . ? N11 Fe1 O1 91.2(2) . . ? C7 Fe1 O1 86.9(3) . . ? C1 Fe1 O1 169.4(2) . . ? N5 Fe1 O2 91.6(2) . . ? N11 Fe1 O2 81.2(2) . . ? C7 Fe1 O2 168.9(3) . . ? C1 Fe1 O2 87.0(2) . . ? O1 Fe1 O2 93.16(19) . . ? C1 N1 N2 113.1(6) . . ? C1 N1 C5 129.0(6) . . ? N2 N1 C5 117.7(6) . . ? C2 N2 N1 106.3(6) . . ? C1 N3 C2 110.9(6) . . ? C1 N3 N4 129.6(6) . . ? C2 N3 N4 119.6(5) . . ? C3 N4 N3 114.6(6) . . ? C3 N5 N6 118.1(6) . . ? C3 N5 Fe1 126.6(5) . . ? N6 N5 Fe1 113.6(4) . . ? C4 N6 N5 112.6(6) . . ? C4 N6 C6 123.5(6) . . ? N5 N6 C6 123.3(5) . . ? C7 N7 N8 115.0(7) . . ? C7 N7 C11 128.8(7) . . ? N8 N7 C11 116.2(6) . . ? C8 N8 N7 100.6(6) . . ? C8 N9 N10 120.1(6) . . ? C8 N9 C7 107.9(5) . . ? N10 N9 C7 131.9(6) . . ? C9 N10 N9 116.5(6) . . ? C9 N11 N12 117.2(5) . . ? C9 N11 Fe1 128.4(5) . . ? N12 N11 Fe1 111.7(4) . . ? C10 N12 C12 123.7(7) . . ? C10 N12 N11 113.8(6) . . ? C12 N12 N11 122.4(5) . . ? C4 O1 Fe1 109.4(4) . . ? C10 O2 Fe1 108.6(4) . . ? H1X O1W H1Y 109.5 . . ? H2X O2W H2Y 109.5 . . ? H3X O3W H3Y 109.5 . . ? 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 N7 C7 Fe1 N5 -29.0(9) . . . . ? N9 C7 Fe1 N5 150.8(6) . . . . ? N7 C7 Fe1 N11 158.7(9) . . . . ? N9 C7 Fe1 N11 -21.5(6) . . . . ? N7 C7 Fe1 C1 59.6(9) . . . . ? N9 C7 Fe1 C1 -120.6(7) . . . . ? N7 C7 Fe1 O1 -110.0(9) . . . . ? N9 C7 Fe1 O1 69.8(6) . . . . ? N7 C7 Fe1 O2 159.3(10) . . . . ? N9 C7 Fe1 O2 -20.9(19) . . . . ? N1 C1 Fe1 N5 160.5(7) . . . . ? N3 C1 Fe1 N5 -19.8(6) . . . . ? N1 C1 Fe1 N11 -27.3(8) . . . . ? N3 C1 Fe1 N11 152.4(6) . . . . ? N1 C1 Fe1 C7 61.2(8) . . . . ? N3 C1 Fe1 C7 -119.1(6) . . . . ? N1 C1 Fe1 O1 160.9(10) . . . . ? N3 C1 Fe1 O1 -19.4(17) . . . . ? N1 C1 Fe1 O2 -107.8(7) . . . . ? N3 C1 Fe1 O2 71.9(6) . . . . ? N3 C1 N1 N2 -6.1(7) . . . . ? Fe1 C1 N1 N2 173.7(6) . . . . ? N3 C1 N1 C5 178.9(6) . . . . ? Fe1 C1 N1 C5 -1.3(12) . . . . ? N3 C2 N2 N1 -2.5(8) . . . . ? C1 N1 N2 C2 5.7(8) . . . . ? C5 N1 N2 C2 -178.7(6) . . . . ? N1 C1 N3 C2 4.3(7) . . . . ? Fe1 C1 N3 C2 -175.5(5) . . . . ? N1 C1 N3 N4 -174.9(6) . . . . ? Fe1 C1 N3 N4 5.3(10) . . . . ? N2 C2 N3 C1 -1.2(8) . . . . ? N2 C2 N3 N4 178.1(5) . . . . ? N5 C3 N4 N3 -8.3(11) . . . . ? C1 N3 N4 C3 13.3(9) . . . . ? C2 N3 N4 C3 -165.9(6) . . . . ? N4 C3 N5 N6 -179.4(7) . . . . ? N4 C3 N5 Fe1 -15.5(11) . . . . ? N11 Fe1 N5 C3 -107.7(14) . . . . ? C7 Fe1 N5 C3 119.8(6) . . . . ? C1 Fe1 N5 C3 25.2(6) . . . . ? O1 Fe1 N5 C3 -154.7(6) . . . . ? O2 Fe1 N5 C3 -61.7(6) . . . . ? N11 Fe1 N5 N6 56.9(15) . . . . ? C7 Fe1 N5 N6 -75.6(5) . . . . ? C1 Fe1 N5 N6 -170.2(4) . . . . ? O1 Fe1 N5 N6 9.8(4) . . . . ? O2 Fe1 N5 N6 102.8(4) . . . . ? O1 C4 N6 N5 8.9(9) . . . . ? O1 C4 N6 C6 -179.4(6) . . . . ? C3 N5 N6 C4 153.1(6) . . . . ? Fe1 N5 N6 C4 -12.9(7) . . . . ? C3 N5 N6 C6 -18.7(9) . . . . ? Fe1 N5 N6 C6 175.4(5) . . . . ? N9 C7 N7 N8 -3.4(9) . . . . ? Fe1 C7 N7 N8 176.5(6) . . . . ? N9 C7 N7 C11 176.1(8) . . . . ? Fe1 C7 N7 C11 -4.1(15) . . . . ? N9 C8 N8 N7 -2.3(9) . . . . ? C7 N7 N8 C8 3.6(9) . . . . ? C11 N7 N8 C8 -175.9(7) . . . . ? N8 C8 N9 N10 176.6(7) . . . . ? N8 C8 N9 C7 0.5(9) . . . . ? N7 C7 N9 C8 1.7(9) . . . . ? Fe1 C7 N9 C8 -178.2(6) . . . . ? N7 C7 N9 N10 -173.7(8) . . . . ? Fe1 C7 N9 N10 6.4(12) . . . . ? N11 C9 N10 N9 -4.1(12) . . . . ? C8 N9 N10 C9 -162.9(8) . . . . ? C7 N9 N10 C9 12.0(12) . . . . ? N10 C9 N11 N12 178.0(7) . . . . ? N10 C9 N11 Fe1 -22.6(12) . . . . ? N5 Fe1 N11 C9 -102.4(14) . . . . ? C7 Fe1 N11 C9 30.9(7) . . . . ? C1 Fe1 N11 C9 125.5(6) . . . . ? O1 Fe1 N11 C9 -56.0(6) . . . . ? O2 Fe1 N11 C9 -149.0(6) . . . . ? N5 Fe1 N11 N12 57.9(15) . . . . ? C7 Fe1 N11 N12 -168.8(5) . . . . ? C1 Fe1 N11 N12 -74.2(5) . . . . ? O1 Fe1 N11 N12 104.3(4) . . . . ? O2 Fe1 N11 N12 11.3(4) . . . . ? O2 C10 N12 C12 173.7(7) . . . . ? O2 C10 N12 N11 -4.1(10) . . . . ? C9 N11 N12 C10 154.5(7) . . . . ? Fe1 N11 N12 C10 -8.2(7) . . . . ? C9 N11 N12 C12 -23.3(10) . . . . ? Fe1 N11 N12 C12 174.0(6) . . . . ? N6 C4 O1 Fe1 -0.7(8) . . . . ? N5 Fe1 O1 C4 -5.2(5) . . . . ? N11 Fe1 O1 C4 -177.6(5) . . . . ? C7 Fe1 O1 C4 94.8(5) . . . . ? C1 Fe1 O1 C4 -5.6(15) . . . . ? O2 Fe1 O1 C4 -96.3(5) . . . . ? N12 C10 O2 Fe1 13.2(9) . . . . ? N5 Fe1 O2 C10 174.4(5) . . . . ? N11 Fe1 O2 C10 -13.2(5) . . . . ? C7 Fe1 O2 C10 -13.8(16) . . . . ? C1 Fe1 O2 C10 86.7(5) . . . . ? O1 Fe1 O2 C10 -103.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.022 _refine_diff_density_min -0.824 _refine_diff_density_rms 0.150 # Attachment '- Rev_1_2.cif' data_1_2 _database_code_depnum_ccdc_archive 'CCDC 869062' #TrackingRef '- Rev_1_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H45 F6 Fe N13 O2 P' _chemical_formula_weight 772.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.6055(17) _cell_length_b 12.6303(13) _cell_length_c 12.6377(19) _cell_angle_alpha 98.8230(10) _cell_angle_beta 95.409(2) _cell_angle_gamma 97.5500(10) _cell_volume 1802.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 806 _exptl_absorpt_coefficient_mu 0.539 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8638 _exptl_absorpt_correction_T_max 0.8906 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 9679 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0771 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6924 _reflns_number_gt 4454 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0400P)^2^+0.4400P] 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 6924 _refine_ls_number_parameters 447 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8404(3) 1.1429(3) 0.8853(3) 0.0526(9) Uani 1 1 d . . . H1A H 0.7717 1.1351 0.8344 0.079 Uiso 1 1 calc R . . H1B H 0.8777 1.2170 0.8985 0.079 Uiso 1 1 calc R . . H1C H 0.8186 1.1227 0.9516 0.079 Uiso 1 1 calc R . . C2 C 0.9241(3) 1.0706(3) 0.8402(3) 0.0496(9) Uani 1 1 d . . . H2A H 0.9976 1.0884 0.8868 0.059 Uiso 1 1 calc R . . H2B H 0.9393 1.0879 0.7701 0.059 Uiso 1 1 calc R . . C3 C 0.8852(3) 0.9480(3) 0.8269(3) 0.0505(9) Uani 1 1 d . . . H3A H 0.9403 0.9159 0.8701 0.061 Uiso 1 1 calc R . . H3B H 0.8089 0.9337 0.8516 0.061 Uiso 1 1 calc R . . C4 C 0.8795(3) 0.8991(3) 0.7110(2) 0.0413(8) Uani 1 1 d . . . H4A H 0.8268 0.9339 0.6682 0.050 Uiso 1 1 calc R . . H4B H 0.9565 0.9122 0.6876 0.050 Uiso 1 1 calc R . . C5 C 0.7274(3) 0.7262(3) 0.6537(2) 0.0422(8) Uani 1 1 d . . . C6 C 0.8554(3) 0.6178(3) 0.6989(3) 0.0440(8) Uani 1 1 d . . . H6 H 0.8844 0.5543 0.7088 0.053 Uiso 1 1 calc R . . C7 C 0.5506(3) 0.5398(3) 0.6259(3) 0.0405(7) Uani 1 1 d . . . H7 H 0.4964 0.4774 0.6192 0.049 Uiso 1 1 calc R . . C8 C 0.3469(3) 0.7073(3) 0.5635(3) 0.0419(8) Uani 1 1 d . . . H8 H 0.2672 0.7074 0.5465 0.050 Uiso 1 1 calc R . . C9 C 0.2959(3) 0.5342(3) 0.6255(2) 0.0408(7) Uani 1 1 d . . . H9A H 0.3131 0.4657 0.5891 0.049 Uiso 1 1 calc R . . H9B H 0.2176 0.5428 0.5974 0.049 Uiso 1 1 calc R . . C10 C 0.3005(3) 0.5324(3) 0.7472(3) 0.0481(8) Uani 1 1 d . . . H10A H 0.2508 0.4680 0.7584 0.058 Uiso 1 1 calc R . . H10B H 0.3800 0.5278 0.7755 0.058 Uiso 1 1 calc R . . C11 C 0.2615(3) 0.6315(3) 0.8100(3) 0.0523(9) Uani 1 1 d . . . H11A H 0.3214 0.6594 0.8702 0.063 Uiso 1 1 calc R . . H11B H 0.2628 0.6859 0.7634 0.063 Uiso 1 1 calc R . . C12 C 0.1448(3) 0.6257(3) 0.8551(3) 0.0524(9) Uani 1 1 d . . . H12A H 0.0895 0.5696 0.8105 0.079 Uiso 1 1 calc R . . H12B H 0.1164 0.6939 0.8563 0.079 Uiso 1 1 calc R . . H12C H 0.1544 0.6100 0.9270 0.079 Uiso 1 1 calc R . . C13 C 0.8500(3) 0.6214(3) 1.0184(2) 0.0423(8) Uani 1 1 d . . . H13A H 0.9039 0.6348 0.9671 0.063 Uiso 1 1 calc R . . H13B H 0.8579 0.5531 1.0406 0.063 Uiso 1 1 calc R . . H13C H 0.8669 0.6781 1.0800 0.063 Uiso 1 1 calc R . . C14 C 0.7242(3) 0.6184(2) 0.9661(2) 0.0390(7) Uani 1 1 d . . . H14A H 0.6701 0.5960 1.0152 0.047 Uiso 1 1 calc R . . H14B H 0.7099 0.5644 0.9010 0.047 Uiso 1 1 calc R . . C15 C 0.6988(3) 0.7278(3) 0.9372(3) 0.0428(8) Uani 1 1 d . . . H15A H 0.7095 0.7808 1.0029 0.051 Uiso 1 1 calc R . . H15B H 0.7558 0.7519 0.8912 0.051 Uiso 1 1 calc R . . C16 C 0.5771(3) 0.7252(3) 0.8805(2) 0.0392(7) Uani 1 1 d . . . H16A H 0.5623 0.6659 0.8200 0.047 Uiso 1 1 calc R . . H16B H 0.5203 0.7110 0.9301 0.047 Uiso 1 1 calc R . . C17 C 0.5665(3) 0.8493(3) 0.7393(2) 0.0419(8) Uani 1 1 d . . . C18 C 0.5435(3) 0.9936(3) 0.8623(2) 0.0382(7) Uani 1 1 d . . . H18 H 0.5348 1.0638 0.8917 0.046 Uiso 1 1 calc R . . C19 C 0.6097(3) 1.0007(3) 0.5878(2) 0.0383(7) Uani 1 1 d . . . H19 H 0.6206 1.0499 0.5407 0.046 Uiso 1 1 calc R . . C20 C 0.6699(3) 0.7868(3) 0.4123(3) 0.0430(8) Uani 1 1 d . . . H20 H 0.6997 0.7687 0.3472 0.052 Uiso 1 1 calc R . . C21 C 0.7716(3) 0.9782(3) 0.4301(3) 0.0477(8) Uani 1 1 d . . . H21A H 0.8475 0.9539 0.4295 0.057 Uiso 1 1 calc R . . H21B H 0.7801 1.0399 0.4878 0.057 Uiso 1 1 calc R . . C22 C 0.7478(3) 1.0203(3) 0.3262(3) 0.0525(9) Uani 1 1 d . . . H22A H 0.8085 1.0806 0.3249 0.063 Uiso 1 1 calc R . . H22B H 0.6741 1.0486 0.3270 0.063 Uiso 1 1 calc R . . C23 C 0.7419(3) 0.9409(3) 0.2221(3) 0.0559(10) Uani 1 1 d . . . H23A H 0.6664 0.8951 0.2054 0.067 Uiso 1 1 calc R . . H23B H 0.8032 0.8958 0.2252 0.067 Uiso 1 1 calc R . . C24 C 0.7604(3) 1.0189(3) 0.1397(3) 0.0531(9) Uani 1 1 d . . . H24A H 0.7292 1.0842 0.1630 0.080 Uiso 1 1 calc R . . H24B H 0.7210 0.9846 0.0703 0.080 Uiso 1 1 calc R . . H24C H 0.8426 1.0363 0.1347 0.080 Uiso 1 1 calc R . . C25 C 0.3301(3) 0.6965(3) 0.2474(3) 0.0539(10) Uani 1 1 d . . . H25A H 0.3357 0.6428 0.2930 0.081 Uiso 1 1 calc R . . H25B H 0.2612 0.6753 0.1963 0.081 Uiso 1 1 calc R . . H25C H 0.3254 0.7649 0.2907 0.081 Uiso 1 1 calc R . . C26 C 0.4341(3) 0.7067(3) 0.1897(3) 0.0496(9) Uani 1 1 d . . . F1 F 0.02747(17) 0.61302(15) 0.34330(16) 0.0540(5) Uani 1 1 d . . . F2 F 0.06670(16) 0.67901(16) 0.51269(15) 0.0520(5) Uani 1 1 d . . . F3 F 0.13592(16) 0.77146(16) 0.39264(15) 0.0492(5) Uani 1 1 d . . . F4 F -0.05042(16) 0.75307(15) 0.31229(15) 0.0466(5) Uani 1 1 d . . . F5 F -0.11849(15) 0.66832(14) 0.43749(14) 0.0445(5) Uani 1 1 d . . . F6 F -0.00896(16) 0.82375(15) 0.48346(15) 0.0515(5) Uani 1 1 d . . . Fe1 Fe 0.58300(4) 0.77019(4) 0.60357(4) 0.03963(13) Uani 1 1 d . . . N1 N 0.8383(2) 0.7810(2) 0.6924(2) 0.0388(6) Uani 1 1 d . . . N2 N 0.9172(2) 0.7129(2) 0.7198(2) 0.0398(6) Uani 1 1 d . . . N3 N 0.7417(2) 0.6217(2) 0.6603(2) 0.0395(6) Uani 1 1 d . . . N4 N 0.6587(2) 0.5256(2) 0.6401(2) 0.0397(6) Uani 1 1 d . . . N5 N 0.5037(2) 0.6320(2) 0.6191(2) 0.0400(6) Uani 1 1 d . . . N6 N 0.3813(2) 0.6241(2) 0.6026(2) 0.0415(6) Uani 1 1 d . . . N7 N 0.5606(2) 0.8255(2) 0.8415(2) 0.0413(6) Uani 1 1 d . . . N8 N 0.5454(2) 0.9143(2) 0.9169(2) 0.0370(6) Uani 1 1 d . . . N9 N 0.5563(2) 0.9600(2) 0.7542(2) 0.0366(6) Uani 1 1 d . . . N10 N 0.5639(2) 1.0335(2) 0.68217(19) 0.0357(6) Uani 1 1 d . . . N11 N 0.6390(2) 0.9035(2) 0.5604(2) 0.0413(6) Uani 1 1 d . . . N12 N 0.6903(2) 0.8899(2) 0.4621(2) 0.0410(6) Uani 1 1 d . . . N13 N 0.5166(3) 0.7136(2) 0.1436(2) 0.0496(7) Uani 1 1 d . . . O1 O 0.4200(2) 0.78923(18) 0.54785(17) 0.0446(5) Uani 1 1 d . . . O2 O 0.61257(19) 0.71442(17) 0.44993(16) 0.0397(5) Uani 1 1 d . . . P1 P 0.00741(7) 0.71898(7) 0.41269(6) 0.03632(19) 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 C1 0.059(2) 0.049(2) 0.054(2) 0.0209(17) 0.0063(17) 0.0107(18) C2 0.047(2) 0.0451(19) 0.053(2) 0.0098(16) 0.0132(16) -0.0114(16) C3 0.047(2) 0.0412(19) 0.056(2) -0.0107(16) 0.0157(16) -0.0064(16) C4 0.0369(18) 0.0462(19) 0.0423(18) 0.0153(15) -0.0093(14) 0.0127(14) C5 0.048(2) 0.0454(19) 0.0309(16) 0.0077(14) -0.0051(14) 0.0030(16) C6 0.045(2) 0.0408(18) 0.0380(17) -0.0090(14) -0.0126(14) 0.0081(15) C7 0.0338(17) 0.0421(18) 0.0503(19) 0.0124(15) 0.0172(14) 0.0087(14) C8 0.0344(17) 0.0427(19) 0.0428(18) 0.0006(15) -0.0054(14) 0.0000(15) C9 0.0367(17) 0.0397(18) 0.0403(17) -0.0103(14) 0.0014(14) 0.0073(14) C10 0.045(2) 0.0456(19) 0.0451(19) -0.0074(15) 0.0016(15) -0.0060(16) C11 0.049(2) 0.047(2) 0.050(2) -0.0152(16) 0.0114(16) -0.0081(16) C12 0.051(2) 0.051(2) 0.058(2) 0.0162(17) 0.0197(17) -0.0001(17) C13 0.0434(19) 0.052(2) 0.0395(17) 0.0162(15) 0.0200(14) 0.0182(15) C14 0.051(2) 0.0359(17) 0.0343(16) 0.0063(13) 0.0137(14) 0.0157(15) C15 0.049(2) 0.0391(17) 0.0430(18) 0.0030(14) 0.0139(15) 0.0139(15) C16 0.0455(19) 0.0396(17) 0.0342(16) 0.0088(14) 0.0128(14) 0.0041(14) C17 0.0442(19) 0.0433(18) 0.0375(17) 0.0044(14) 0.0130(14) 0.0008(15) C18 0.0373(18) 0.0369(17) 0.0372(17) 0.0079(14) -0.0078(13) 0.0006(14) C19 0.0444(18) 0.0435(18) 0.0267(15) -0.0002(13) 0.0018(13) 0.0141(14) C20 0.050(2) 0.0369(18) 0.0378(17) -0.0027(14) -0.0026(15) 0.0068(15) C21 0.060(2) 0.0389(18) 0.0418(18) -0.0059(14) 0.0194(16) 0.0036(16) C22 0.040(2) 0.061(2) 0.060(2) 0.0158(18) 0.0136(16) 0.0083(17) C23 0.045(2) 0.074(3) 0.048(2) 0.0141(19) 0.0065(17) 0.0027(18) C24 0.048(2) 0.059(2) 0.046(2) 0.0170(17) -0.0088(16) -0.0138(17) C25 0.049(2) 0.045(2) 0.060(2) -0.0088(17) 0.0182(17) -0.0097(16) C26 0.051(2) 0.047(2) 0.047(2) -0.0063(16) 0.0171(17) 0.0019(16) F1 0.0502(12) 0.0464(11) 0.0611(13) -0.0137(9) 0.0039(10) 0.0190(9) F2 0.0429(11) 0.0608(12) 0.0465(11) 0.0230(9) -0.0085(8) -0.0201(9) F3 0.0390(11) 0.0560(12) 0.0588(12) 0.0219(10) 0.0180(9) 0.0069(9) F4 0.0444(11) 0.0529(11) 0.0511(11) 0.0210(9) 0.0137(8) 0.0182(9) F5 0.0370(10) 0.0476(11) 0.0475(11) 0.0156(9) 0.0045(8) -0.0071(8) F6 0.0464(11) 0.0435(10) 0.0536(11) -0.0212(9) 0.0233(9) -0.0120(9) Fe1 0.0353(3) 0.0378(3) 0.0428(3) 0.0004(2) 0.00550(19) 0.00137(19) N1 0.0356(14) 0.0437(15) 0.0397(15) 0.0066(12) 0.0146(11) 0.0090(12) N2 0.0409(15) 0.0374(15) 0.0429(15) 0.0128(12) 0.0093(12) 0.0026(12) N3 0.0383(15) 0.0408(15) 0.0432(15) 0.0113(12) 0.0159(12) 0.0069(12) N4 0.0318(15) 0.0478(16) 0.0409(15) 0.0117(12) 0.0086(11) 0.0031(12) N5 0.0332(15) 0.0458(16) 0.0444(15) 0.0095(12) 0.0132(12) 0.0095(12) N6 0.0345(15) 0.0427(15) 0.0516(16) 0.0098(13) 0.0137(12) 0.0137(12) N7 0.0425(15) 0.0418(15) 0.0421(15) 0.0127(12) 0.0131(12) 0.0025(12) N8 0.0359(14) 0.0417(15) 0.0349(14) 0.0108(12) -0.0027(11) 0.0110(11) N9 0.0308(13) 0.0362(14) 0.0366(14) 0.0025(11) -0.0099(11) -0.0036(11) N10 0.0297(13) 0.0387(14) 0.0382(14) 0.0012(11) 0.0098(11) 0.0055(11) N11 0.0433(16) 0.0411(15) 0.0347(14) -0.0018(11) 0.0000(11) 0.0013(12) N12 0.0412(16) 0.0381(15) 0.0492(16) 0.0111(12) 0.0142(12) 0.0156(12) N13 0.0540(18) 0.0432(16) 0.0435(16) -0.0103(12) 0.0138(14) -0.0084(13) O1 0.0426(13) 0.0500(14) 0.0411(12) 0.0110(10) 0.0057(10) 0.0015(11) O2 0.0455(13) 0.0421(12) 0.0342(11) 0.0122(10) -0.0042(9) 0.0156(10) P1 0.0396(4) 0.0372(4) 0.0306(4) 0.0010(3) 0.0083(3) 0.0024(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 C1 C2 1.511(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.534(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.491(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N1 1.482(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N3 1.366(4) . ? C5 N1 1.384(4) . ? C5 Fe1 1.916(3) . ? C6 N2 1.292(4) . ? C6 N3 1.373(4) . ? C6 H6 0.9300 . ? C7 N4 1.291(4) . ? C7 N5 1.360(4) . ? C7 H7 0.9300 . ? C8 O1 1.302(4) . ? C8 N6 1.318(4) . ? C8 H8 0.9300 . ? C9 N6 1.488(4) . ? C9 C10 1.538(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.521(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.515(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.538(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.540(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.516(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N7 1.457(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N7 1.376(4) . ? C17 N9 1.404(4) . ? C17 Fe1 1.888(3) . ? C18 N8 1.302(4) . ? C18 N9 1.395(4) . ? C18 H18 0.9300 . ? C19 N11 1.320(4) . ? C19 N10 1.379(4) . ? C19 H19 0.9300 . ? C20 O2 1.240(4) . ? C20 N12 1.337(4) . ? C20 H20 0.9300 . ? C21 N12 1.494(4) . ? C21 C22 1.506(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.516(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.551(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.470(5) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 N13 1.168(4) . ? F1 P1 1.5409(19) . ? F2 P1 1.565(2) . ? F3 P1 1.6096(19) . ? F4 P1 1.526(2) . ? F5 P1 1.5953(19) . ? F6 P1 1.5238(19) . ? Fe1 N11 1.901(3) . ? Fe1 N5 1.910(3) . ? Fe1 O1 2.013(2) . ? Fe1 O2 2.038(2) . ? N1 N2 1.391(4) . ? N3 N4 1.420(4) . ? N5 N6 1.404(4) . ? N7 N8 1.397(4) . ? N9 N10 1.397(3) . ? N11 N12 1.425(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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 C3 116.9(3) . . ? C1 C2 H2A 108.1 . . ? C3 C2 H2A 108.1 . . ? C1 C2 H2B 108.1 . . ? C3 C2 H2B 108.1 . . ? H2A C2 H2B 107.3 . . ? C4 C3 C2 109.2(3) . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3B 109.8 . . ? C2 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? N1 C4 C3 111.8(3) . . ? N1 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? N1 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? N3 C5 N1 101.6(3) . . ? N3 C5 Fe1 124.4(2) . . ? N1 C5 Fe1 134.0(2) . . ? N2 C6 N3 111.8(3) . . ? N2 C6 H6 124.1 . . ? N3 C6 H6 124.1 . . ? N4 C7 N5 130.0(3) . . ? N4 C7 H7 115.0 . . ? N5 C7 H7 115.0 . . ? O1 C8 N6 122.7(3) . . ? O1 C8 H8 118.7 . . ? N6 C8 H8 118.7 . . ? N6 C9 C10 111.4(2) . . ? N6 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? N6 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 113.3(3) . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C12 C11 C10 121.9(3) . . ? C12 C11 H11A 106.9 . . ? C10 C11 H11A 106.9 . . ? C12 C11 H11B 106.9 . . ? C10 C11 H11B 106.9 . . ? H11A C11 H11B 106.7 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C13 C14 C15 113.7(3) . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14B 108.8 . . ? C15 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 114.5(3) . . ? C16 C15 H15A 108.6 . . ? C14 C15 H15A 108.6 . . ? C16 C15 H15B 108.6 . . ? C14 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? N7 C16 C15 113.4(3) . . ? N7 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? N7 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? N7 C17 N9 102.4(3) . . ? N7 C17 Fe1 135.2(3) . . ? N9 C17 Fe1 122.4(2) . . ? N8 C18 N9 111.5(3) . . ? N8 C18 H18 124.3 . . ? N9 C18 H18 124.3 . . ? N11 C19 N10 123.9(3) . . ? N11 C19 H19 118.0 . . ? N10 C19 H19 118.0 . . ? O2 C20 N12 122.2(3) . . ? O2 C20 H20 118.9 . . ? N12 C20 H20 118.9 . . ? N12 C21 C22 122.3(3) . . ? N12 C21 H21A 106.8 . . ? C22 C21 H21A 106.8 . . ? N12 C21 H21B 106.8 . . ? C22 C21 H21B 106.8 . . ? H21A C21 H21B 106.6 . . ? C21 C22 C23 117.2(3) . . ? C21 C22 H22A 108.0 . . ? C23 C22 H22A 108.0 . . ? C21 C22 H22B 108.0 . . ? C23 C22 H22B 108.0 . . ? H22A C22 H22B 107.2 . . ? C22 C23 C24 101.4(3) . . ? C22 C23 H23A 111.5 . . ? C24 C23 H23A 111.5 . . ? C22 C23 H23B 111.5 . . ? C24 C23 H23B 111.5 . . ? H23A C23 H23B 109.3 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N13 C26 C25 179.3(4) . . ? C17 Fe1 N11 88.32(13) . . ? C17 Fe1 N5 99.14(13) . . ? N11 Fe1 N5 167.56(11) . . ? C17 Fe1 C5 93.70(14) . . ? N11 Fe1 C5 100.74(13) . . ? N5 Fe1 C5 88.76(13) . . ? C17 Fe1 O1 90.19(12) . . ? N11 Fe1 O1 88.42(10) . . ? N5 Fe1 O1 81.66(10) . . ? C5 Fe1 O1 170.13(12) . . ? C17 Fe1 O2 168.53(12) . . ? N11 Fe1 O2 80.21(10) . . ? N5 Fe1 O2 92.16(10) . . ? C5 Fe1 O2 88.46(11) . . ? O1 Fe1 O2 89.52(9) . . ? C5 N1 N2 113.2(3) . . ? C5 N1 C4 128.6(3) . . ? N2 N1 C4 118.2(2) . . ? C6 N2 N1 103.6(3) . . ? C5 N3 C6 109.8(3) . . ? C5 N3 N4 130.4(3) . . ? C6 N3 N4 119.7(3) . . ? C7 N4 N3 115.4(3) . . ? C7 N5 N6 118.1(3) . . ? C7 N5 Fe1 127.7(2) . . ? N6 N5 Fe1 113.3(2) . . ? C8 N6 N5 112.5(3) . . ? C8 N6 C9 121.7(3) . . ? N5 N6 C9 125.9(3) . . ? C17 N7 N8 113.2(3) . . ? C17 N7 C16 128.8(3) . . ? N8 N7 C16 117.8(2) . . ? C18 N8 N7 104.6(2) . . ? C18 N9 N10 121.2(2) . . ? C18 N9 C17 108.3(2) . . ? N10 N9 C17 130.4(2) . . ? C19 N10 N9 116.3(2) . . ? C19 N11 N12 113.9(3) . . ? C19 N11 Fe1 129.7(2) . . ? N12 N11 Fe1 113.30(19) . . ? C20 N12 N11 111.7(3) . . ? C20 N12 C21 125.2(3) . . ? N11 N12 C21 122.4(2) . . ? C8 O1 Fe1 108.8(2) . . ? C20 O2 Fe1 110.6(2) . . ? F6 P1 F4 91.91(12) . . ? F6 P1 F1 178.26(13) . . ? F4 P1 F1 89.54(11) . . ? F6 P1 F2 90.56(12) . . ? F4 P1 F2 177.50(12) . . ? F1 P1 F2 87.99(12) . . ? F6 P1 F5 87.59(10) . . ? F4 P1 F5 89.21(11) . . ? F1 P1 F5 93.39(11) . . ? F2 P1 F5 90.54(10) . . ? F6 P1 F3 91.06(11) . . ? F4 P1 F3 92.61(11) . . ? F1 P1 F3 87.91(11) . . ? F2 P1 F3 87.71(11) . . ? F5 P1 F3 177.77(11) . . ? 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 C1 C2 C3 C4 119.8(3) . . . . ? C2 C3 C4 N1 -178.0(3) . . . . ? N6 C9 C10 C11 65.4(4) . . . . ? C9 C10 C11 C12 106.9(4) . . . . ? C13 C14 C15 C16 177.1(2) . . . . ? C14 C15 C16 N7 -172.3(2) . . . . ? N12 C21 C22 C23 -62.2(4) . . . . ? C21 C22 C23 C24 -161.1(3) . . . . ? N7 C17 Fe1 N11 -158.3(4) . . . . ? N9 C17 Fe1 N11 22.0(3) . . . . ? N7 C17 Fe1 N5 31.7(4) . . . . ? N9 C17 Fe1 N5 -148.0(3) . . . . ? N7 C17 Fe1 C5 -57.6(4) . . . . ? N9 C17 Fe1 C5 122.6(3) . . . . ? N7 C17 Fe1 O1 113.3(4) . . . . ? N9 C17 Fe1 O1 -66.5(3) . . . . ? N7 C17 Fe1 O2 -158.2(4) . . . . ? N9 C17 Fe1 O2 22.1(8) . . . . ? N3 C5 Fe1 C17 113.9(3) . . . . ? N1 C5 Fe1 C17 -65.0(3) . . . . ? N3 C5 Fe1 N11 -157.1(3) . . . . ? N1 C5 Fe1 N11 24.0(3) . . . . ? N3 C5 Fe1 N5 14.8(3) . . . . ? N1 C5 Fe1 N5 -164.1(3) . . . . ? N3 C5 Fe1 O1 0.8(9) . . . . ? N1 C5 Fe1 O1 -178.1(5) . . . . ? N3 C5 Fe1 O2 -77.4(3) . . . . ? N1 C5 Fe1 O2 103.7(3) . . . . ? N3 C5 N1 N2 0.9(3) . . . . ? Fe1 C5 N1 N2 180.0(2) . . . . ? N3 C5 N1 C4 -176.6(3) . . . . ? Fe1 C5 N1 C4 2.5(5) . . . . ? C3 C4 N1 C5 99.8(4) . . . . ? C3 C4 N1 N2 -77.5(3) . . . . ? N3 C6 N2 N1 -0.3(3) . . . . ? C5 N1 N2 C6 -0.4(3) . . . . ? C4 N1 N2 C6 177.4(3) . . . . ? N1 C5 N3 C6 -1.0(3) . . . . ? Fe1 C5 N3 C6 179.8(2) . . . . ? N1 C5 N3 N4 175.0(3) . . . . ? Fe1 C5 N3 N4 -4.2(4) . . . . ? N2 C6 N3 C5 0.9(4) . . . . ? N2 C6 N3 N4 -175.6(3) . . . . ? N5 C7 N4 N3 5.6(5) . . . . ? C5 N3 N4 C7 -9.5(4) . . . . ? C6 N3 N4 C7 166.2(3) . . . . ? N4 C7 N5 N6 179.7(3) . . . . ? N4 C7 N5 Fe1 11.8(5) . . . . ? C17 Fe1 N5 C7 -112.4(3) . . . . ? N11 Fe1 N5 C7 121.3(5) . . . . ? C5 Fe1 N5 C7 -18.9(3) . . . . ? O1 Fe1 N5 C7 158.7(3) . . . . ? O2 Fe1 N5 C7 69.5(3) . . . . ? C17 Fe1 N5 N6 79.2(2) . . . . ? N11 Fe1 N5 N6 -47.0(6) . . . . ? C5 Fe1 N5 N6 172.8(2) . . . . ? O1 Fe1 N5 N6 -9.60(19) . . . . ? O2 Fe1 N5 N6 -98.8(2) . . . . ? O1 C8 N6 N5 -3.2(4) . . . . ? O1 C8 N6 C9 176.6(3) . . . . ? C7 N5 N6 C8 -159.7(3) . . . . ? Fe1 N5 N6 C8 9.9(3) . . . . ? C7 N5 N6 C9 20.6(4) . . . . ? Fe1 N5 N6 C9 -169.9(2) . . . . ? C10 C9 N6 C8 -112.4(3) . . . . ? C10 C9 N6 N5 67.3(4) . . . . ? N9 C17 N7 N8 1.1(3) . . . . ? Fe1 C17 N7 N8 -178.8(3) . . . . ? N9 C17 N7 C16 -173.6(3) . . . . ? Fe1 C17 N7 C16 6.6(6) . . . . ? C15 C16 N7 C17 98.3(4) . . . . ? C15 C16 N7 N8 -76.1(3) . . . . ? N9 C18 N8 N7 0.3(3) . . . . ? C17 N7 N8 C18 -0.9(4) . . . . ? C16 N7 N8 C18 174.4(3) . . . . ? N8 C18 N9 N10 -176.1(2) . . . . ? N8 C18 N9 C17 0.3(3) . . . . ? N7 C17 N9 C18 -0.8(3) . . . . ? Fe1 C17 N9 C18 179.0(2) . . . . ? N7 C17 N9 N10 175.1(3) . . . . ? Fe1 C17 N9 N10 -5.0(5) . . . . ? N11 C19 N10 N9 4.2(4) . . . . ? C18 N9 N10 C19 161.7(3) . . . . ? C17 N9 N10 C19 -13.8(4) . . . . ? N10 C19 N11 N12 -176.8(3) . . . . ? N10 C19 N11 Fe1 24.7(5) . . . . ? C17 Fe1 N11 C19 -33.5(3) . . . . ? N5 Fe1 N11 C19 93.7(6) . . . . ? C5 Fe1 N11 C19 -126.9(3) . . . . ? O1 Fe1 N11 C19 56.7(3) . . . . ? O2 Fe1 N11 C19 146.5(3) . . . . ? C17 Fe1 N11 N12 167.9(2) . . . . ? N5 Fe1 N11 N12 -64.9(6) . . . . ? C5 Fe1 N11 N12 74.5(2) . . . . ? O1 Fe1 N11 N12 -101.8(2) . . . . ? O2 Fe1 N11 N12 -12.07(19) . . . . ? O2 C20 N12 N11 0.1(4) . . . . ? O2 C20 N12 C21 171.1(3) . . . . ? C19 N11 N12 C20 -151.4(3) . . . . ? Fe1 N11 N12 C20 10.7(3) . . . . ? C19 N11 N12 C21 37.4(4) . . . . ? Fe1 N11 N12 C21 -160.5(2) . . . . ? C22 C21 N12 C20 67.5(4) . . . . ? C22 C21 N12 N11 -122.5(3) . . . . ? N6 C8 O1 Fe1 -4.6(4) . . . . ? C17 Fe1 O1 C8 -91.5(2) . . . . ? N11 Fe1 O1 C8 -179.8(2) . . . . ? N5 Fe1 O1 C8 7.7(2) . . . . ? C5 Fe1 O1 C8 21.8(8) . . . . ? O2 Fe1 O1 C8 100.0(2) . . . . ? N12 C20 O2 Fe1 -10.0(4) . . . . ? C17 Fe1 O2 C20 12.0(7) . . . . ? N11 Fe1 O2 C20 12.1(2) . . . . ? N5 Fe1 O2 C20 -177.8(2) . . . . ? C5 Fe1 O2 C20 -89.1(2) . . . . ? O1 Fe1 O2 C20 100.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.611 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.054 # Attachment '- Rev_1_4.cif' data_1_4 _database_code_depnum_ccdc_archive 'CCDC 889218' #TrackingRef '- Rev_1_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H18 Fe N12 O2, C H2 Cl2' _chemical_formula_sum 'C13 H20 Cl2 Fe N12 O2' _chemical_formula_weight 503.16 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6334(12) _cell_length_b 8.7729(13) _cell_length_c 14.2422(14) _cell_angle_alpha 78.270(2) _cell_angle_beta 74.950(3) _cell_angle_gamma 75.447(2) _cell_volume 997.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1777 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 26.31 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 1.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7548 _exptl_absorpt_correction_T_max 0.7995 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6756 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3580 _reflns_number_gt 2771 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.05P)^2^+1.22P] 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 3580 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6831(5) 0.6733(4) 0.7031(3) 0.0321(9) Uani 1 1 d . . . C2 C 0.4197(5) 0.6637(5) 0.7043(3) 0.0345(9) Uani 1 1 d . . . H2 H 0.3170 0.6324 0.7244 0.041 Uiso 1 1 calc R . . C3 C 0.6479(5) 0.4441(5) 0.8813(3) 0.0368(9) Uani 1 1 d . . . H3 H 0.6359 0.3616 0.9356 0.044 Uiso 1 1 calc R . . C4 C 1.0546(5) 0.4508(5) 0.8766(3) 0.0336(9) Uani 1 1 d . . . H4 H 1.1386 0.4070 0.9122 0.040 Uiso 1 1 calc R . . C5 C 0.8719(5) 0.2915(5) 0.9985(3) 0.0376(9) Uani 1 1 d . . . H5A H 0.9706 0.2420 1.0242 0.056 Uiso 1 1 calc R . . H5B H 0.8305 0.2093 0.9809 0.056 Uiso 1 1 calc R . . H5C H 0.7877 0.3455 1.0488 0.056 Uiso 1 1 calc R . . C6 C 0.7002(5) 0.8879(5) 0.5547(3) 0.0359(9) Uani 1 1 d . . . H6A H 0.7996 0.8958 0.5729 0.054 Uiso 1 1 calc R . . H6B H 0.6236 0.9914 0.5543 0.054 Uiso 1 1 calc R . . H6C H 0.7292 0.8564 0.4892 0.054 Uiso 1 1 calc R . . C7 C 0.8310(6) 0.8249(5) 0.7928(3) 0.0456(11) Uani 1 1 d . . . C8 C 0.8262(5) 1.0815(5) 0.7962(3) 0.0379(10) Uani 1 1 d . . . H8 H 0.8476 1.1855 0.7744 0.046 Uiso 1 1 calc R . . C9 C 1.0704(5) 0.8605(5) 0.6037(3) 0.0408(10) Uani 1 1 d . . . H9 H 1.1572 0.8738 0.5479 0.049 Uiso 1 1 calc R . . C10 C 1.0770(6) 0.4620(5) 0.5962(3) 0.0386(10) Uani 1 1 d . . . H10 H 1.1296 0.3795 0.5574 0.046 Uiso 1 1 calc R . . C11 C 1.2430(5) 0.6386(5) 0.4766(3) 0.0387(10) Uani 1 1 d . . . H11D H 1.2930 0.5416 0.4466 0.058 Uiso 1 1 calc R . . H11E H 1.3273 0.6756 0.4952 0.058 Uiso 1 1 calc R . . H11F H 1.1931 0.7214 0.4294 0.058 Uiso 1 1 calc R . . C12 C 0.6235(5) 0.8001(5) 0.9530(3) 0.0343(9) Uani 1 1 d . . . H12A H 0.5531 0.7602 0.9239 0.051 Uiso 1 1 calc R . . H12B H 0.5552 0.8751 0.9974 0.051 Uiso 1 1 calc R . . H12C H 0.6872 0.7108 0.9900 0.051 Uiso 1 1 calc R . . C13 C 0.7252(5) 0.8851(5) 0.2641(3) 0.0399(10) Uani 1 1 d . . . H13A H 0.6998 0.9658 0.3085 0.048 Uiso 1 1 calc R . . H13B H 0.8288 0.8111 0.2742 0.048 Uiso 1 1 calc R . . Cl1 Cl 0.56803(14) 0.77722(14) 0.29924(8) 0.0457(3) Uani 1 1 d . . . Cl2 Cl 0.75598(14) 0.97728(14) 0.14882(8) 0.0491(3) Uani 1 1 d . . . Fe1 Fe 0.88488(7) 0.62711(8) 0.74209(4) 0.03498(19) Uani 1 1 d . . . N1 N 0.6232(4) 0.7690(4) 0.6259(2) 0.0329(7) Uani 1 1 d . . . N2 N 0.4613(4) 0.7703(4) 0.6263(2) 0.0354(8) Uani 1 1 d . . . N3 N 0.5494(4) 0.6053(4) 0.7519(2) 0.0342(8) Uani 1 1 d . . . N4 N 0.5206(4) 0.4984(4) 0.8387(2) 0.0374(8) Uani 1 1 d . . . N5 N 0.7917(4) 0.4916(5) 0.8568(2) 0.0380(8) Uani 1 1 d . . . N6 N 0.9120(4) 0.4072(4) 0.9115(3) 0.0368(8) Uani 1 1 d . . . N7 N 0.7346(4) 0.8808(4) 0.8755(3) 0.0395(8) Uani 1 1 d . . . N8 N 0.7307(4) 1.0402(4) 0.8801(3) 0.0404(9) Uani 1 1 d . . . N9 N 0.8928(4) 0.9564(4) 0.7428(3) 0.0389(8) Uani 1 1 d . . . N10 N 1.0045(5) 0.9837(5) 0.6529(2) 0.0413(9) Uani 1 1 d . . . N11 N 1.0248(4) 0.7168(4) 0.6259(2) 0.0353(8) Uani 1 1 d . . . N12 N 1.1190(4) 0.6051(4) 0.5626(2) 0.0372(8) Uani 1 1 d . . . O1 O 1.0846(3) 0.5444(3) 0.80097(19) 0.0317(6) Uani 1 1 d . . . O2 O 0.9767(3) 0.4286(3) 0.67251(19) 0.0355(6) 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 C1 0.0253(19) 0.0245(19) 0.037(2) -0.0043(16) -0.0030(16) 0.0083(15) C2 0.035(2) 0.031(2) 0.045(2) -0.0005(18) -0.0111(18) -0.0222(17) C3 0.036(2) 0.032(2) 0.046(2) -0.0024(18) -0.0176(18) -0.0081(17) C4 0.036(2) 0.034(2) 0.032(2) -0.0038(17) -0.0091(17) -0.0082(17) C5 0.046(2) 0.033(2) 0.039(2) -0.0008(18) -0.0164(19) -0.0133(19) C6 0.031(2) 0.030(2) 0.035(2) -0.0025(17) 0.0033(16) 0.0030(16) C7 0.052(3) 0.026(2) 0.053(3) 0.0003(19) -0.012(2) -0.0023(19) C8 0.038(2) 0.042(2) 0.0284(19) -0.0070(18) 0.0070(17) -0.0118(19) C9 0.041(2) 0.032(2) 0.047(2) -0.0219(19) 0.0057(19) -0.0058(18) C10 0.050(3) 0.036(2) 0.0256(19) -0.0108(17) -0.0004(18) -0.0043(19) C11 0.049(3) 0.038(2) 0.033(2) -0.0059(18) -0.0048(18) -0.020(2) C12 0.0242(19) 0.034(2) 0.048(2) -0.0021(18) -0.0118(17) -0.0119(16) C13 0.035(2) 0.043(2) 0.050(2) -0.015(2) -0.0116(19) -0.0143(19) Cl1 0.0421(6) 0.0439(6) 0.0466(6) -0.0112(5) -0.0007(5) -0.0068(5) Cl2 0.0455(6) 0.0477(6) 0.0424(6) -0.0088(5) 0.0079(5) -0.0052(5) Fe1 0.0287(3) 0.0413(4) 0.0322(3) -0.0107(3) -0.0101(2) 0.0053(2) N1 0.0274(17) 0.0349(18) 0.0327(17) -0.0019(14) -0.0016(13) -0.0076(14) N2 0.0256(17) 0.0319(18) 0.0389(18) -0.0068(15) -0.0001(14) 0.0058(14) N3 0.0243(16) 0.0350(18) 0.0336(17) -0.0037(14) -0.0011(13) 0.0048(14) N4 0.043(2) 0.0356(19) 0.0398(18) -0.0073(16) -0.0114(16) -0.0162(16) N5 0.0377(19) 0.053(2) 0.0285(16) -0.0079(15) -0.0153(14) -0.0096(17) N6 0.043(2) 0.0301(18) 0.0448(19) -0.0021(15) -0.0182(16) -0.0141(15) N7 0.0397(19) 0.0207(16) 0.050(2) -0.0004(15) 0.0031(16) -0.0095(14) N8 0.043(2) 0.0342(19) 0.0384(18) -0.0113(15) 0.0106(16) -0.0127(16) N9 0.0288(18) 0.041(2) 0.0412(19) -0.0097(16) 0.0079(15) -0.0096(15) N10 0.045(2) 0.048(2) 0.0265(16) -0.0141(15) 0.0040(15) -0.0071(17) N11 0.0337(18) 0.0341(19) 0.0378(18) -0.0101(15) -0.0086(15) -0.0023(15) N12 0.044(2) 0.0267(17) 0.0333(17) -0.0028(14) -0.0006(15) -0.0028(15) O1 0.0270(13) 0.0352(15) 0.0344(14) -0.0094(12) -0.0055(11) -0.0073(11) O2 0.0360(15) 0.0374(15) 0.0347(14) -0.0051(12) -0.0015(12) -0.0174(12) _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 C1 N1 1.372(5) . ? C1 N3 1.390(5) . ? C1 Fe1 1.888(4) . ? C2 N2 1.333(5) . ? C2 N3 1.394(5) . ? C2 H2 0.9500 . ? C3 N4 1.329(5) . ? C3 N5 1.346(5) . ? C3 H3 0.9500 . ? C4 O1 1.227(5) . ? C4 N6 1.323(5) . ? C4 H4 0.9500 . ? C5 N6 1.458(5) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 N1 1.458(5) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 N7 1.356(6) . ? C7 N9 1.379(6) . ? C7 Fe1 1.918(5) . ? C8 N8 1.304(5) . ? C8 N9 1.382(5) . ? C8 H8 0.9500 . ? C9 N10 1.332(5) . ? C9 N11 1.366(6) . ? C9 H9 0.9500 . ? C10 O2 1.236(5) . ? C10 N12 1.353(6) . ? C10 H10 0.9500 . ? C11 N12 1.436(5) . ? C11 H11D 0.9800 . ? C11 H11E 0.9800 . ? C11 H11F 0.9800 . ? C12 N7 1.454(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 Cl2 1.661(5) . ? C13 Cl1 1.757(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? Fe1 N11 1.931(3) . ? Fe1 N5 1.934(4) . ? Fe1 O1 2.020(3) . ? Fe1 O2 2.060(3) . ? N1 N2 1.394(5) . ? N3 N4 1.398(5) . ? N5 N6 1.426(5) . ? N7 N8 1.405(5) . ? N9 N10 1.406(5) . ? N11 N12 1.419(5) . ? 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 C1 N3 100.5(3) . . ? N1 C1 Fe1 134.6(3) . . ? N3 C1 Fe1 125.0(3) . . ? N2 C2 N3 109.8(3) . . ? N2 C2 H2 125.1 . . ? N3 C2 H2 125.1 . . ? N4 C3 N5 128.0(4) . . ? N4 C3 H3 116.0 . . ? N5 C3 H3 116.0 . . ? O1 C4 N6 123.8(4) . . ? O1 C4 H4 118.1 . . ? N6 C4 H4 118.1 . . ? N6 C5 H5A 109.5 . . ? N6 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N6 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N7 C7 N9 101.4(4) . . ? N7 C7 Fe1 135.6(3) . . ? N9 C7 Fe1 123.0(3) . . ? N8 C8 N9 112.2(4) . . ? N8 C8 H8 123.9 . . ? N9 C8 H8 123.9 . . ? N10 C9 N11 126.0(4) . . ? N10 C9 H9 117.0 . . ? N11 C9 H9 117.0 . . ? O2 C10 N12 126.1(4) . . ? O2 C10 H10 116.9 . . ? N12 C10 H10 116.9 . . ? N12 C11 H11D 109.5 . . ? N12 C11 H11E 109.5 . . ? H11D C11 H11E 109.5 . . ? N12 C11 H11F 109.5 . . ? H11D C11 H11F 109.5 . . ? H11E C11 H11F 109.5 . . ? N7 C12 H12A 109.5 . . ? N7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? Cl2 C13 Cl1 115.9(2) . . ? Cl2 C13 H13A 108.3 . . ? Cl1 C13 H13A 108.3 . . ? Cl2 C13 H13B 108.3 . . ? Cl1 C13 H13B 108.3 . . ? H13A C13 H13B 107.4 . . ? C1 Fe1 C7 91.41(19) . . ? C1 Fe1 N11 101.72(15) . . ? C7 Fe1 N11 89.97(17) . . ? C1 Fe1 N5 88.47(15) . . ? C7 Fe1 N5 100.36(18) . . ? N11 Fe1 N5 165.36(15) . . ? C1 Fe1 O1 169.44(14) . . ? C7 Fe1 O1 93.07(16) . . ? N11 Fe1 O1 87.85(13) . . ? N5 Fe1 O1 81.31(13) . . ? C1 Fe1 O2 93.62(14) . . ? C7 Fe1 O2 170.29(17) . . ? N11 Fe1 O2 80.89(13) . . ? N5 Fe1 O2 88.07(13) . . ? O1 Fe1 O2 83.40(11) . . ? C1 N1 N2 115.6(3) . . ? C1 N1 C6 126.5(3) . . ? N2 N1 C6 116.9(3) . . ? C2 N2 N1 103.1(3) . . ? C1 N3 C2 110.9(3) . . ? C1 N3 N4 132.7(3) . . ? C2 N3 N4 116.4(3) . . ? C3 N4 N3 114.5(3) . . ? C3 N5 N6 116.7(3) . . ? C3 N5 Fe1 130.6(3) . . ? N6 N5 Fe1 111.3(3) . . ? C4 N6 N5 112.8(3) . . ? C4 N6 C5 126.1(4) . . ? N5 N6 C5 121.1(3) . . ? C7 N7 N8 115.2(3) . . ? C7 N7 C12 127.1(4) . . ? N8 N7 C12 117.3(3) . . ? C8 N8 N7 101.9(3) . . ? C7 N9 C8 109.2(3) . . ? C7 N9 N10 133.1(4) . . ? C8 N9 N10 117.6(3) . . ? C9 N10 N9 116.7(4) . . ? C9 N11 N12 114.3(3) . . ? C9 N11 Fe1 130.4(3) . . ? N12 N11 Fe1 114.1(2) . . ? C10 N12 N11 110.1(3) . . ? C10 N12 C11 125.1(4) . . ? N11 N12 C11 124.8(3) . . ? C4 O1 Fe1 110.6(3) . . ? C10 O2 Fe1 108.6(3) . . ? 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 N1 C1 Fe1 C7 77.8(4) . . . . ? N3 C1 Fe1 C7 -104.2(3) . . . . ? N1 C1 Fe1 N11 -12.4(4) . . . . ? N3 C1 Fe1 N11 165.5(3) . . . . ? N1 C1 Fe1 N5 178.2(4) . . . . ? N3 C1 Fe1 N5 -3.9(3) . . . . ? N1 C1 Fe1 O1 -167.1(6) . . . . ? N3 C1 Fe1 O1 10.9(10) . . . . ? N1 C1 Fe1 O2 -93.9(4) . . . . ? N3 C1 Fe1 O2 84.1(3) . . . . ? N7 C7 Fe1 C1 78.1(5) . . . . ? N9 C7 Fe1 C1 -101.2(4) . . . . ? N7 C7 Fe1 N11 179.8(5) . . . . ? N9 C7 Fe1 N11 0.5(4) . . . . ? N7 C7 Fe1 N5 -10.6(5) . . . . ? N9 C7 Fe1 N5 170.0(4) . . . . ? N7 C7 Fe1 O1 -92.4(5) . . . . ? N9 C7 Fe1 O1 88.3(4) . . . . ? N3 C1 N1 N2 2.9(4) . . . . ? Fe1 C1 N1 N2 -178.8(3) . . . . ? N3 C1 N1 C6 171.4(3) . . . . ? Fe1 C1 N1 C6 -10.3(6) . . . . ? N3 C2 N2 N1 2.5(4) . . . . ? C1 N1 N2 C2 -3.5(4) . . . . ? C6 N1 N2 C2 -173.2(3) . . . . ? N1 C1 N3 C2 -1.1(4) . . . . ? Fe1 C1 N3 C2 -179.6(3) . . . . ? N1 C1 N3 N4 -178.1(4) . . . . ? Fe1 C1 N3 N4 3.4(6) . . . . ? N2 C2 N3 C1 -1.0(5) . . . . ? N2 C2 N3 N4 176.5(3) . . . . ? N5 C3 N4 N3 7.5(6) . . . . ? C1 N3 N4 C3 -3.9(6) . . . . ? C2 N3 N4 C3 179.3(4) . . . . ? N4 C3 N5 N6 -176.7(4) . . . . ? N4 C3 N5 Fe1 -11.2(7) . . . . ? C1 Fe1 N5 C3 7.7(4) . . . . ? C7 Fe1 N5 C3 98.8(4) . . . . ? N11 Fe1 N5 C3 -126.9(6) . . . . ? O1 Fe1 N5 C3 -169.6(4) . . . . ? O2 Fe1 N5 C3 -86.0(4) . . . . ? C1 Fe1 N5 N6 173.8(3) . . . . ? C7 Fe1 N5 N6 -95.1(3) . . . . ? N11 Fe1 N5 N6 39.2(7) . . . . ? O1 Fe1 N5 N6 -3.5(2) . . . . ? O2 Fe1 N5 N6 80.1(3) . . . . ? O1 C4 N6 N5 -5.4(6) . . . . ? O1 C4 N6 C5 177.2(4) . . . . ? C3 N5 N6 C4 173.8(4) . . . . ? Fe1 N5 N6 C4 5.6(4) . . . . ? C3 N5 N6 C5 -8.7(5) . . . . ? Fe1 N5 N6 C5 -176.9(3) . . . . ? N9 C7 N7 N8 0.6(5) . . . . ? Fe1 C7 N7 N8 -178.8(4) . . . . ? N9 C7 N7 C12 173.4(4) . . . . ? Fe1 C7 N7 C12 -6.0(7) . . . . ? N9 C8 N8 N7 -2.4(5) . . . . ? C7 N7 N8 C8 1.1(5) . . . . ? C12 N7 N8 C8 -172.5(4) . . . . ? N7 C7 N9 C8 -2.0(5) . . . . ? Fe1 C7 N9 C8 177.5(3) . . . . ? N7 C7 N9 N10 177.9(4) . . . . ? Fe1 C7 N9 N10 -2.6(7) . . . . ? N8 C8 N9 C7 2.9(5) . . . . ? N8 C8 N9 N10 -177.0(4) . . . . ? N11 C9 N10 N9 8.7(7) . . . . ? C7 N9 N10 C9 -1.5(7) . . . . ? C8 N9 N10 C9 178.4(4) . . . . ? N10 C9 N11 N12 -178.3(4) . . . . ? N10 C9 N11 Fe1 -12.0(7) . . . . ? C1 Fe1 N11 C9 97.6(4) . . . . ? C7 Fe1 N11 C9 6.1(4) . . . . ? N5 Fe1 N11 C9 -129.1(6) . . . . ? O1 Fe1 N11 C9 -87.0(4) . . . . ? O2 Fe1 N11 C9 -170.6(4) . . . . ? C1 Fe1 N11 N12 -96.1(3) . . . . ? C7 Fe1 N11 N12 172.5(3) . . . . ? N5 Fe1 N11 N12 37.3(7) . . . . ? O1 Fe1 N11 N12 79.4(3) . . . . ? O2 Fe1 N11 N12 -4.2(2) . . . . ? O2 C10 N12 N11 -2.7(6) . . . . ? O2 C10 N12 C11 176.1(4) . . . . ? C9 N11 N12 C10 173.6(4) . . . . ? Fe1 N11 N12 C10 4.9(4) . . . . ? C9 N11 N12 C11 -5.3(5) . . . . ? Fe1 N11 N12 C11 -173.9(3) . . . . ? N6 C4 O1 Fe1 2.3(5) . . . . ? C1 Fe1 O1 C4 -14.0(9) . . . . ? C7 Fe1 O1 C4 101.0(3) . . . . ? N11 Fe1 O1 C4 -169.2(3) . . . . ? N5 Fe1 O1 C4 0.9(3) . . . . ? O2 Fe1 O1 C4 -88.1(3) . . . . ? N12 C10 O2 Fe1 -0.7(5) . . . . ? C1 Fe1 O2 C10 104.1(3) . . . . ? N11 Fe1 O2 C10 2.8(3) . . . . ? N5 Fe1 O2 C10 -167.6(3) . . . . ? O1 Fe1 O2 C10 -86.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.301 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.067