Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Harry Goodwin' 'Donald C. Craig' 'Wendy-Anne McHale' 'A. David Rae' 'Marcia L. Scudder' 'Kristian H. Sugiyarto' _publ_contact_author_name 'Prof Harry Goodwin' _publ_contact_author_address ; School of Chemical Sciences University of New South Wales UNSW Sydney NSW 2052 AUSTRALIA ; _publ_contact_author_email H.GOODWIN@UNSW.EDU.AU _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Spin transition centres linked by the nitroprusside ion. The cooperative transition in bis(2,6-bis(pyrazol-3-yl)pyridine)iron(II) nitroprusside ; _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. De Meulenaer, J. and Tompa, H. Acta Cryst., 1965, 19, 1014. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1989. ; data_C22H18FeN10,C5FeN6O_DHG72_RT _database_code_CSD 202880 _audit_creation_method 'RAELSPUB and manual entry' _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C22 H18 Fe N10 2+,C5 Fe N6 O 2-' _chemical_formula_sum 'C27 H18 Fe2 N16 O' _chemical_formula_iupac ? _chemical_formula_weight 694.2 # CRYSTAL DATA _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 4/ncc' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,y,1/2+z 3 x,1/2-y,1/2+z 4 1/2-x,1/2-y,z 5 y,x,1/2+z 6 1/2-y,x,z 7 y,1/2-x,z 8 1/2-y,1/2-x,1/2+z 9 -x,-y,-z 10 1/2+x,-y,1/2-z 11 -x,1/2+y,1/2-z 12 1/2+x,1/2+y,-z 13 -y,-x,1/2-z 14 1/2+y,-x,-z 15 -y,1/2+x,-z 16 1/2+y,1/2+x,1/2-z _cell_length_a 13.346(3) _cell_length_b 13.346(3) _cell_length_c 17.273(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3077(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 10 _cell_measurement_theta_min 9 _cell_measurement_theta_max 11 _cell_measurement_temperature 294 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.50 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408.0 _exptl_absorpt_coefficient_mu 0.991 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.89 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 2620 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 1361 _reflns_number_gt 875 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.034 _refine_ls_wR_factor_ref 0.041 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 875 _refine_ls_number_parameters 112 _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.003 _refine_diff_density_max 0.51 _refine_diff_density_min -0.50 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Fe1 0.7500 0.2500 0.2500 0.0367(2) Uani Fe 1.0 N1 0.8560(2) 0.2904(2) 0.1585(2) 0.0455(7) Uani N 1.0 N2 0.8604(2) 0.3567(2) 0.1002(2) 0.0583(8) Uani N 1.0 N3 0.8635(2) 0.1365(2) 0.2500 0.0461(9) Uani N 1.0 C1 0.9360(4) 0.3355(3) 0.0518(2) 0.074(1) Uani C 1.0 C2 0.9825(3) 0.2518(4) 0.0785(2) 0.075(1) Uani C 1.0 C3 0.9307(3) 0.2250(3) 0.1457(2) 0.0524(9) Uani C 1.0 C4 0.9383(3) 0.1412(3) 0.1986(2) 0.055(1) Uani C 1.0 C5 1.0136(3) 0.0693(4) 0.1978(3) 0.086(2) Uani C 1.0 C6 1.0075(3) -0.0075(3) 0.2500 0.106(3) Uani C 1.0 Fe2 0.25000 0.25000 0.36190(4) 0.0398(2) Uani Fe 1.0 O1Np 0.2748(78) 0.2315(96) 0.2028(3) 0.118(9) Uani O 1.0 N1Np 0.2500 0.2500 0.2669(3) 0.074(2) Uani N 1.0 N2Np 0.2500 0.2500 0.5398(3) 0.072(2) Uani N 1.0 C2Np 0.2500 0.2500 0.4745(4) 0.046(1) Uani C 1.0 N3Np 0.0216(3) 0.2344(3) 0.3788(2) 0.081(1) Uani N 1.0 C3Np 0.1063(3) 0.2390(3) 0.3720(2) 0.0528(9) Uani C 1.0 HN2 0.8134 0.4144 0.0936 0.058 Uani H 1.0 HC1 0.9548 0.3743 0.0045 0.074 Uani H 1.0 HC2 1.0414 0.2168 0.0551 0.075 Uani H 1.0 HC5 1.0704 0.0735 0.1602 0.086 Uani H 1.0 HC6 1.0605 -0.0605 0.2500 0.106 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Fe1 0.0310(3) 0.0310(3) 0.0482(5) 0.0073(5) 0.0000 0.0000 Fe N1 0.039(2) 0.045(2) 0.053(2) -0.001(1) 0.002(1) -0.006(1) N N2 0.062(2) 0.056(2) 0.057(2) -0.009(2) 0.010(2) 0.004(2) N N3 0.041(1) 0.041(1) 0.056(2) 0.013(2) -0.012(1) -0.012(1) N C1 0.073(3) 0.087(3) 0.063(3) -0.020(2) 0.023(2) -0.006(2) C C2 0.052(2) 0.106(3) 0.066(2) -0.001(3) 0.015(2) -0.024(3) C C3 0.036(2) 0.066(3) 0.056(2) 0.002(2) 0.002(2) -0.021(2) C C4 0.040(2) 0.067(2) 0.059(2) 0.021(2) -0.009(2) -0.027(2) C C5 0.066(3) 0.108(4) 0.085(3) 0.051(3) -0.011(2) -0.034(3) C C6 0.112(4) 0.112(4) 0.092(5) 0.085(5) -0.024(4) -0.024(4) C Fe2 0.0433(3) 0.0433(3) 0.0327(4) 0.0000 0.0000 0.0000 Fe O1Np 0.162(9) 0.162(9) 0.031(3) 0.0000 0.0000 0.0000 O N1Np 0.093(3) 0.093(3) 0.038(3) 0.0000 0.0000 0.0000 N N2Np 0.091(3) 0.091(3) 0.034(3) 0.0000 0.0000 0.0000 N C2Np 0.044(2) 0.044(2) 0.048(3) 0.0000 0.0000 0.0000 C N3Np 0.048(2) 0.119(3) 0.076(2) -0.003(2) -0.006(2) -0.013(2) N C3Np 0.050(2) 0.064(3) 0.045(2) 0.000(2) -0.006(1) -0.006(2) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N1 2.189(3) 1_555 1_555 no Fe1 N1 2.189(3) 1_555 4_655 no Fe1 N1 2.189(3) 1_555 13_665 no Fe1 N1 2.189(3) 1_555 16_545 no Fe1 N3 2.143(3) 1_555 1_555 no Fe1 N3 2.143(3) 1_555 4_655 no N1 C3 1.343(4) 1_555 1_555 no N2 C1 1.340(5) 1_555 1_555 no N3 C4 1.337(4) 1_555 1_555 no N3 C4 1.337(4) 1_555 13_665 no C1 C2 1.358(6) 1_555 1_555 no C2 C3 1.397(5) 1_555 1_555 no C3 C4 1.449(4) 1_555 1_555 no C4 C5 1.390(5) 1_555 1_555 no C5 C6 1.367(6) 1_555 1_555 no C6 C5 1.367(6) 1_555 13_665 no Fe2 N1Np 1.640(5) 1_555 1_555 no Fe2 C2Np 1.945(6) 1_555 1_555 no Fe2 C3Np 1.931(4) 1_555 1_555 no Fe2 C3Np 1.931(4) 1_555 4_555 no Fe2 C3Np 1.931(4) 1_555 6_555 no Fe2 C3Np 1.931(4) 1_555 7_555 no O1Np N1Np 1.182(18) 1_555 1_555 no N2Np C2Np 1.129(8) 1_555 1_555 no N3Np C3Np 1.139(4) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 87.5(1) 1_555 1_555 4_655 no N1 Fe1 N1 147.2(1) 1_555 1_555 13_665 no N1 Fe1 N1 101.7(1) 1_555 1_555 16_545 no N1 Fe1 N3 73.58(7) 1_555 1_555 1_555 no N1 Fe1 N3 106.42(7) 1_555 1_555 4_655 no N1 Fe1 N1 101.7(1) 4_655 1_555 13_665 no N1 Fe1 N1 147.2(1) 4_655 1_555 16_545 no N1 Fe1 N3 106.42(7) 4_655 1_555 1_555 no N1 Fe1 N3 73.58(7) 4_655 1_555 4_655 no N1 Fe1 N1 87.5(1) 13_665 1_555 16_545 no N1 Fe1 N3 73.58(7) 13_665 1_555 1_555 no N1 Fe1 N3 106.42(7) 13_665 1_555 4_655 no N1 Fe1 N3 106.42(7) 16_545 1_555 1_555 no N1 Fe1 N3 73.58(7) 16_545 1_555 4_655 no N3 Fe1 N3 180.00 1_555 1_555 4_655 no Fe1 N1 C3 116.0(2) 1_555 1_555 1_555 no Fe1 N3 C4 119.7(2) 1_555 1_555 1_555 no Fe1 N3 C4 119.7(2) 1_555 1_555 13_665 no C4 N3 C4 120.7(4) 1_555 1_555 13_665 no N2 C1 C2 107.8(4) 1_555 1_555 1_555 no C1 C2 C3 105.4(4) 1_555 1_555 1_555 no N1 C3 C2 109.7(4) 1_555 1_555 1_555 no N1 C3 C4 116.8(3) 1_555 1_555 1_555 no C2 C3 C4 133.4(4) 1_555 1_555 1_555 no N3 C4 C3 113.7(3) 1_555 1_555 1_555 no N3 C4 C5 120.9(4) 1_555 1_555 1_555 no C3 C4 C5 125.3(4) 1_555 1_555 1_555 no C4 C5 C6 117.8(5) 1_555 1_555 1_555 no C5 C6 C5 121.7(6) 1_555 1_555 13_665 no N1Np Fe2 C2Np 180.00 1_555 1_555 1_555 no N1Np Fe2 C3Np 95.17(9) 1_555 1_555 1_555 no N1Np Fe2 C3Np 95.17(9) 1_555 1_555 4_555 no N1Np Fe2 C3Np 95.17(9) 1_555 1_555 6_555 no N1Np Fe2 C3Np 95.17(9) 1_555 1_555 7_555 no C2Np Fe2 C3Np 84.83(9) 1_555 1_555 1_555 no C2Np Fe2 C3Np 84.83(9) 1_555 1_555 4_555 no C2Np Fe2 C3Np 84.83(9) 1_555 1_555 6_555 no C2Np Fe2 C3Np 84.83(9) 1_555 1_555 7_555 no C3Np Fe2 C3Np 169.7(2) 1_555 1_555 4_555 no C3Np Fe2 C3Np 89.53(2) 1_555 1_555 6_555 no C3Np Fe2 C3Np 89.53(2) 1_555 1_555 7_555 no C3Np Fe2 C3Np 89.53(2) 4_555 1_555 6_555 no C3Np Fe2 C3Np 89.53(2) 4_555 1_555 7_555 no C3Np Fe2 C3Np 169.7(2) 6_555 1_555 7_555 no Fe2 N1Np O1Np 159.6(21) 1_555 1_555 1_555 no Fe2 C2Np N2Np 180.00 1_555 1_555 1_555 no Fe2 C3Np N3Np 178.5(4) 1_555 1_555 1_555 no data_C22H18FeN10,C5FeN6O_DHG73_LT _database_code_CSD 202881 _audit_creation_method 'RAELSPUB and manual entry' _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1989. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'Denzo-Scalepak (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 2000)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C22 H18 Fe N10 2+,C5 Fe N6 O 2-' _chemical_formula_sum 'C27 H18 Fe2 N16 O' _chemical_formula_iupac ? _chemical_formula_weight 694.2 # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n c a' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,z 3 -x,1/2+y,1/2-z 4 1/2+x,1/2-y,1/2-z 5 -x,-y,-z 6 1/2+x,y,-z 7 x,1/2-y,1/2+z 8 1/2-x,1/2+y,1/2+z _cell_length_a 18.8716(2) _cell_length_b 18.8716(2) _cell_length_c 16.6791(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5940.05(14) _cell_formula_units_Z 8 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 100 _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.56 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2816.0 _exptl_absorpt_coefficient_mu 1.03 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.825 _exptl_absorpt_correction_T_max 0.903 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius KappaCCD area detector diffractometer' _diffrn_ambient_temperature 100(2) _diffrn_reflns_number 61201 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_theta_max 27.50 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_standards_number ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 7104 _reflns_number_gt 5694 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.044 _refine_ls_wR_factor_ref 0.058 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 5694 _refine_ls_number_parameters 119 _refine_ls_goodness_of_fit_ref 1.25 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.25 _refine_diff_density_max 0.61 _refine_diff_density_min -0.83 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom Fe1 0.25000 0.50000 0.22566(4) 1.0 0.0189(2) . Uani d ? N1 0.3228(1) 0.4874(1) 0.1417(1) 1.0 0.022(1) . Uani d ? N2 0.3565(1) 0.5283(1) 0.0876(1) 1.0 0.026(1) . Uani d ? N3 0.2605(0) 0.3981(1) 0.2257(1) 1.0 0.022(1) . Uani d ? N4 0.1832(1) 0.4730(1) 0.3108(1) 1.0 0.021(1) . Uani d ? N5 0.1468(1) 0.5068(1) 0.3687(1) 1.0 0.025(1) . Uani d ? C1 0.3969(1) 0.4878(1) 0.0381(2) 1.0 0.031(1) . Uani d ? C2 0.3894(1) 0.4182(1) 0.0603(2) 1.0 0.030(1) . Uani d ? C3 0.3424(1) 0.4200(1) 0.1256(2) 1.0 0.025(1) . Uani d ? C4 0.3074(1) 0.3673(1) 0.1755(1) 1.0 0.025(1) . Uani d ? C5 0.3163(1) 0.2938(1) 0.1741(2) 1.0 0.032(1) . Uani d ? C6 0.2755(1) 0.2532(1) 0.2258(1) 1.0 0.037(1) . Uani d ? C7 0.1183(1) 0.4596(1) 0.4211(1) 1.0 0.030(1) . Uani d ? C8 0.1367(2) 0.3926(1) 0.3968(2) 1.0 0.031(1) . Uani d ? C9 0.1774(1) 0.4030(1) 0.3273(2) 1.0 0.025(1) . Uani d ? C10 0.2210(1) 0.3584(1) 0.2759(1) 1.0 0.026(1) . Uani d ? C11 0.2273(1) 0.2847(1) 0.2775(2) 1.0 0.034(1) . Uani d ? Fe1' 0.75000 0.50000 0.25987(4) 1.0 0.0209(1) . Uani d ? N1' 0.7661(1) 0.5716(1) 0.1763(1) 1.0 0.024(1) . Uani d ? N2' 0.7253(1) 0.6076(1) 0.1241(1) 1.0 0.028(1) . Uani d ? N3' 0.8523(1) 0.5026(1) 0.2556(1) 1.0 0.026(1) . Uani d ? N4' 0.7738(1) 0.4316(1) 0.3455(1) 1.0 0.025(1) . Uani d ? N5' 0.7400(1) 0.3963(1) 0.4043(1) 1.0 0.030(1) . Uani d ? C1' 0.7662(1) 0.6451(1) 0.0721(2) 1.0 0.034(1) . Uani d ? C2' 0.8360(1) 0.6333(2) 0.0909(2) 1.0 0.035(1) . Uani d ? C3' 0.8339(1) 0.5869(1) 0.1567(1) 1.0 0.028(1) . Uani d ? C4' 0.8850(1) 0.5468(1) 0.2038(1) 1.0 0.031(1) . Uani d ? C5' 0.9589(1) 0.5500(2) 0.1993(2) 1.0 0.043(1) . Uani d ? C6' 0.9979(1) 0.5064(1) 0.2496(1) 1.0 0.050(1) . Uani d ? C7' 0.7874(1) 0.3648(1) 0.4542(2) 1.0 0.036(1) . Uani d ? C8' 0.8545(1) 0.3800(2) 0.4273(2) 1.0 0.038(1) . Uani d ? C9' 0.8439(1) 0.4221(1) 0.3589(1) 1.0 0.030(1) . Uani d ? C10' 0.8905(1) 0.4603(1) 0.3045(1) 1.0 0.032(1) . Uani d ? C11' 0.9645(1) 0.4609(2) 0.3029(2) 1.0 0.044(1) . Uani d ? Fe2 0.50976(2) 0.25871(2) 0.37135(3) 1.0 0.0212(2) . Uani d ? N1Np 0.5283(1) 0.2618(1) 0.2749(2) 1.0 0.027(1) . Uani d ? O1Np 0.5438(9) 0.2515(4) 0.2080(3) 0.371(14) 0.036(1) . Uani d ? C2Np 0.4937(2) 0.2519(1) 0.4864(2) 1.0 0.024(1) . Uani d ? N2Np 0.4828(2) 0.2465(1) 0.5538(2) 1.0 0.031(1) . Uani d ? C3Np 0.4226(1) 0.3123(1) 0.3692(2) 1.0 0.028(1) . Uani d ? N3Np 0.3723(2) 0.3465(2) 0.3692(2) 1.0 0.038(1) . Uani d ? C4Np 0.5592(2) 0.3460(2) 0.3951(2) 1.0 0.027(1) . Uani d ? N4Np 0.5907(2) 0.3969(1) 0.4074(2) 1.0 0.037(1) . Uani d ? C5Np 0.5962(2) 0.2075(2) 0.3940(2) 1.0 0.026(1) . Uani d ? N5Np 0.6479(1) 0.1771(2) 0.4061(2) 1.0 0.035(1) . Uani d ? C6Np 0.4555(2) 0.1718(2) 0.3673(2) 1.0 0.027(1) . Uani d ? N6Np 0.4214(2) 0.1214(1) 0.3673(2) 1.0 0.036(1) . Uani d ? O1Np1 0.5532(4) 0.2666(10) 0.2109(2) 0.361(14) 0.036(1) . Uani d ? O1Np2 0.5385(10) 0.2763(4) 0.2077(3) 0.236(14) 0.036(1) . Uani d ? O1Np3 0.5291(4) 0.2612(10) 0.2047(2) 0.032(14) 0.036(1) . Uani d ? HN2 0.3525 0.5810 0.0844 1.0 0.028 . Uani c ? HC1 0.4270 0.5058 -0.0069 1.0 0.038 . Uani c ? HC2 0.4122 0.3757 0.0355 1.0 0.036 . Uani c ? HC5 0.3511 0.2711 0.1369 1.0 0.037 . Uani c ? HC6 0.2810 0.2005 0.2258 1.0 0.045 . Uani c ? HN5 0.1415 0.5594 0.3726 1.0 0.026 . Uani c ? HC7 0.0891 0.4717 0.4692 1.0 0.036 . Uani c ? HC8 0.1239 0.3466 0.4228 1.0 0.038 . Uani c ? HC11 0.1979 0.2554 0.3148 1.0 0.040 . Uani c ? HN2' 0.6723 0.6069 0.1236 1.0 0.030 . Uani c ? HC1' 0.7484 0.6760 0.0278 1.0 0.040 . Uani c ? HC2' 0.8788 0.6533 0.0638 1.0 0.043 . Uani c ? HC5' 0.9829 0.5828 0.1609 1.0 0.050 . Uani c ? HC6' 1.0508 0.5078 0.2474 1.0 0.064 . Uani c ? HN5' 0.6874 0.3936 0.4103 1.0 0.032 . Uani c ? HC7' 0.7755 0.3356 0.5023 1.0 0.043 . Uani c ? HC8' 0.9006 0.3645 0.4511 1.0 0.046 . Uani c ? HC11' 0.9926 0.4295 0.3392 1.0 .0.053 . Uani c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Fe1 0.0179(3) 0.0192(3) 0.0196(3) 0.0000(2) 0.0000 0.0000 N1 0.020(1) 0.025(1) 0.021(1) 0.002(1) 0.002(1) 0.001(1) N2 0.023(1) 0.031(1) 0.024(1) 0.001(1) 0.005(1) 0.000(1) N3 0.023(1) 0.019(1) 0.023(1) 0.001(1) 0.000(1) 0.000(1) N4 0.020(1) 0.023(1) 0.022(1) 0.000(1) 0.002(1) 0.001(1) N5 0.022(1) 0.030(1) 0.023(1) 0.002(1) 0.003(1) 0.001(1) C1 0.027(1) 0.042(1) 0.025(1) 0.005(1) 0.007(1) 0.003(1) C2 0.028(1) 0.038(1) 0.024(1) 0.009(1) 0.004(1) -0.002(1) C3 0.024(1) 0.027(1) 0.022(1) 0.005(1) 0.002(1) -0.002(1) C4 0.028(1) 0.022(1) 0.025(1) 0.004(1) 0.000(1) -0.002(1) C5 0.041(1) 0.023(1) 0.033(1) 0.008(1) -0.001(1) -0.004(1) C6 0.050(1) 0.019(1) 0.040(1) 0.003(1) 0.000(1) -0.001(1) C7 0.026(1) 0.038(1) 0.027(1) 0.001(1) 0.007(1) 0.006(1) C8 0.030(1) 0.033(1) 0.031(1) -0.004(1) 0.007(1) 0.008(1) C9 0.025(1) 0.024(1) 0.027(1) -0.003(12) 0.003(1) 0.004(1) C10 0.029(1) 0.020(1) 0.028(1) -0.002(12) 0.001(1) 0.002(1) C11 0.043(1) 0.020(1) 0.038(1) -0.002(10) 0.001(1) 0.003(1) Fe1' 0.0174(3) 0.0212(3) 0.0242(3) 0.0012(2) 0.0000 0.0000 N1' 0.024(1) 0.022(1) 0.025(1) 0.000(1) 0.000(1) 0.001(1) N2' 0.033(1) 0.023(1) 0.027(1) 0.003(1) -0.002(1) 0.002(1) N3' 0.017(1) 0.031(1) 0.030(1) 0.001(1) -0.001(1) 0.000(1) N4' 0.026(1) 0.023(1) 0.025(1) 0.003(1) -0.001(1) 0.001(1) N5' 0.038(1) 0.025(1) 0.026(1) -0.000(1) 0.001(1) 0.002(1) C1' 0.048(1) 0.025(1) 0.028(1) -0.001(0) 0.001(1) 0.003(1) C2' 0.043(1) 0.031(1) 0.030(1) -0.010(1) 0.005(1) 0.003(1) C3' 0.027(1) 0.029(1) 0.029(1) -0.006(1) 0.003(1) 0.001(1) C4' 0.020(1) 0.038(1) 0.034(1) -0.005(1) 0.002(1) 0.000(1) C5' 0.020(1) 0.062(1) 0.046(1) -0.008(1) 0.004(1) 0.000(1) C6' 0.017(1) 0.078(1) 0.056(1) 0.000(1) -0.001(1) 0.000(1) C7' 0.052(1) 0.028(1) 0.028(1) 0.005(1) -0.004(1) 0.004(1) C8' 0.044(1) 0.036(1) 0.033(1) 0.012(1) -0.009(1) 0.004(1) C9' 0.028(1) 0.031(1) 0.030(1) 0.008(1) -0.005(1) 0.002(1) C10' 0.020(1) 0.040(1) 0.035(1) 0.006(1) -0.004(1) 0.001(1) C11' 0.020(1) 0.064(1) 0.048(1) 0.009(1) -0.006(1) 0.001(1) Fe2 0.0223(3) 0.0224(4) 0.0190(3) -0.0010(2) -0.0015(2) 0.0001(2) N1Np 0.028(1) 0.034(1) 0.019(1) -0.003(1) -0.001(1) 0.001(1) O1Np 0.037(1) 0.051(2) 0.019(1) -0.004(1) 0.001(1) -0.001(1) C2Np 0.025(1) 0.029(1) 0.019(1) -0.002(1) -0.001(1) 0.000(1) N2Np 0.032(1) 0.042(1) 0.020(1) -0.004(1) 0.001(1) 0.000(1) C3Np 0.026(1) 0.031(1) 0.028(1) 0.005(1) -0.004(1) 0.000(1) N3Np 0.032(1) 0.042(1) 0.041(1) 0.013(1) -0.006(1) -0.001(1) C4Np 0.031(1) 0.024(1) 0.028(1) -0.005(1) -0.002(1) 0.001(1) N4Np 0.043(1) 0.028(1) 0.040(1) -0.012(1) -0.003(1) 0.000(1) C5Np 0.024(1) 0.029(1) 0.025(1) 0.003(1) -0.002(1) -0.001(1) N5Np 0.028(1) 0.040(1) 0.036(1) 0.009(1) -0.004(1) -0.002(1) C6Np 0.029(1) 0.026(1) 0.026(1) -0.006(1) -0.002(1) -0.002(1) N6Np 0.039(1) 0.031(1) 0.038(1) -0.013(1) -0.003(1) -0.003(1) O1Np1 0.037(1) 0.051(2) 0.020(1) -0.005(1) 0.002(1) 0.001(1) O1Np2 0.038(1) 0.051(2) 0.020(1) -0.005(1) 0.000(1) 0.003(1) O1Np3 0.038(2) 0.051(2) 0.019(1) -0.005(1) 0.000(1) 0.001(1) HN2 0.027 0.031 0.027 -0.002 0.006 0.006 HC1 0.031 0.053 0.029 0.006 0.011 0.006 HC2 0.035 0.045 0.027 0.015 0.005 -0.004 HC5 0.048 0.027 0.035 0.013 0.000 -0.006 HC6 0.065 0.020 0.050 0.005 0.000 -0.001 HN5 0.024 0.031 0.022 0.005 0.003 -0.001 HC7 0.031 0.048 0.029 0.004 0.010 0.007 HC8 0.038 0.037 0.038 -0.006 0.010 0.012 HC11 0.051 0.022 0.046 -0.006 0.003 0.007 HN2' 0.033 0.028 0.029 0.009 -0.004 0.002 HC1' 0.064 0.027 0.029 0.001 -0.001 0.005 HC2' 0.051 0.040 0.036 -0.018 0.010 0.004 HC5' 0.026 0.072 0.052 -0.017 0.008 0.001 HC6' 0.017 0.105 0.070 -0.001 -0.001 0.000 HN5' 0.039 0.028 0.028 -0.005 0.004 0.002 HC7' 0.069 0.030 0.029 0.004 -0.004 0.006 HC8' 0.052 0.048 0.040 0.019 -0.015 0.005 HC11' 0.026 0.077 0.056 0.017 -0.011 0.001 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N1 1.976(2) . . yes Fe1 N3 1.933(2) . . yes Fe1 N4 1.967(2) . . yes N1 N2 1.346(2) . . yes N1 C3 1.353(2) . . yes N2 C1 1.359(2) . . yes N3 C4 1.350(2) . . yes N3 C10 1.350(2) . . yes N4 N5 1.346(2) . . yes N4 C9 1.353(2) . . yes N5 C7 1.359(2) . . yes C1 C2 1.373(3) . . yes C2 C3 1.405(3) . . yes C3 C4 1.455(3) . . yes C4 C5 1.396(2) . . yes C5 C6 1.387(2) . . yes C6 C11 1.387(2) . . yes C7 C8 1.373(3) . . yes C8 C9 1.405(3) . . yes C9 C10 1.456(3) . . yes C10 C11 1.396(2) . . yes Fe1' N1' 1.965(2) . . yes Fe1' N3' 1.933(2) . . yes Fe1' N4' 1.976(2) . . yes N1' N2' 1.346(2) . . yes N1' C3' 1.353(2) . . yes N2' C1' 1.359(2) . . yes N3' C4' 1.350(2) . . yes N3' C10' 1.350(2) . . yes N4' N5' 1.346(2) . . yes N4' C9' 1.353(2) . . yes N5' C7' 1.359(2) . . yes C1' C2' 1.373(3) . . yes C2' C3' 1.405(3) . . yes C3' C4' 1.456(3) . . yes C4' C5' 1.396(2) . . yes C5' C6' 1.387(2) . . yes C6' C11' 1.387(2) . . yes C7' C8' 1.373(3) . . yes C8' C9' 1.405(3) . . yes C9' C10' 1.455(3) . . yes C10' C11' 1.396(2) . . yes Fe2 N1Np 1.647(3) . . yes Fe2 C2Np 1.948(3) . . yes Fe2 C3Np 1.931(3) . . yes Fe2 C4Np 1.934(3) . . yes Fe2 C5Np 1.933(3) . . yes Fe2 C6Np 1.935(3) . . yes N1Np O1Np 1.170(4) . . yes N1Np O1Np1 1.170(4) . . yes N1Np O1Np2 1.170(4) . . yes N1Np O1Np3 1.170(4) . . yes C2Np N2Np 1.147(5) . . yes C3Np N3Np 1.148(3) . . yes C4Np N4Np 1.148(3) . . yes C5Np N5Np 1.149(3) . . yes C6Np N6Np 1.149(3) . . yes N2 N5Np 2.811(3) . 3_655 yes N5 N3Np 2.791(3) . 2_565 yes N2' N6Np 2.784(3) . 3_655 yes N5' N4Np 2.819(4) . . yes N2Np O1Np 2.818(12) . 7_555 yes N2Np O1Np1 2.948(6) . 7_555 yes N2Np O1Np2 2.806(12) . 7_555 yes N2Np O1Np3 2.668(6) . 7_555 yes N2 HN2 1.000 . . no C1 HC1 1.000 . . no C2 HC2 1.000 . . no C5 HC5 1.000 . . no C6 HC6 1.000 . . no N5 HN5 1.000 . . no C7 HC7 1.000 . . no C8 HC8 1.000 . . no C11 HC11 1.000 . . no N2' HN2' 1.000 . . no C1' HC1' 1.000 . . no C2' HC2' 1.000 . . no C5' HC5' 1.000 . . no C6' HC6' 1.000 . . no N5' HN5' 1.000 . . no C7' HC7' 1.000 . . no C8' HC8' 1.000 . . no C11' HC11' 1.000 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 89.7(1) . . 2_565 yes N1 Fe1 N3 79.0(1) . . . yes N1 Fe1 N3 101.0(1) . . 2_565 yes N1 Fe1 N4 157.9(1) . . . yes N1 Fe1 N4 95.6(1) . . 2_565 yes N3 Fe1 N3 179.9(1) . . 2_565 yes N3 Fe1 N4 78.9(1) . . . yes N3 Fe1 N4 101.1(1) . . 2_565 yes N4 Fe1 N4 87.5(1) . . 2_565 yes Fe1 N1 N2 137.3(1) . . . yes Fe1 N1 C3 116.3(1) . . . yes N2 N1 C3 106.1(1) . . . yes N1 N2 C1 110.6(1) . . . yes Fe1 N3 C4 119.8(1) . . . yes Fe1 N3 C10 119.8(1) . . . yes C4 N3 C10 120.5(2) . . . yes Fe1 N4 N5 136.2(1) . . . yes Fe1 N4 C9 116.8(1) . . . yes N5 N4 C9 106.1(1) . . . yes N4 N5 C7 110.6(1) . . . yes N2 C1 C2 108.4(2) . . . yes C1 C2 C3 104.6(2) . . . yes N1 C3 C2 110.4(2) . . . yes N1 C3 C4 113.9(2) . . . yes C2 C3 C4 135.5(2) . . . yes N3 C4 C3 110.9(2) . . . yes N3 C4 C5 121.2(2) . . . yes C3 C4 C5 127.9(2) . . . yes C4 C5 C6 118.1(2) . . . yes C5 C6 C11 120.9(2) . . . yes N5 C7 C8 108.4(2) . . . yes C7 C8 C9 104.6(2) . . . yes N4 C9 C8 110.4(2) . . . yes N4 C9 C10 113.6(2) . . . yes C8 C9 C10 135.5(2) . . . yes N3 C10 C9 110.8(2) . . . yes N3 C10 C11 121.2(2) . . . yes C9 C10 C11 127.9(2) . . . yes C6 C11 C10 118.1(2) . . . yes N1' Fe1' N1' 89.7(1) . . 2_665 yes N1' Fe1' N3' 78.6(1) . . . yes N1' Fe1' N3' 98.4(1) . . 2_665 yes N1' Fe1' N4' 157.9(1) . . . yes N1' Fe1' N4' 95.7(1) . . 2_665 yes N3' Fe1' N3' 175.8(0) . . 2_665 yes N3' Fe1' N4' 79.4(1) . . . yes N3' Fe1' N4' 103.7(1) . . 2_665 yes N4' Fe1' N4' 87.4(1) . . 2_665 yes Fe1' N1' N2' 135.9(1) . . . yes Fe1' N1' C3' 117.6(1) . . . yes N2' N1' C3' 106.1(1) . . . yes N1' N2' C1' 110.6(1) . . . yes Fe1' N3' C4' 119.8(1) . . . yes Fe1' N3' C10' 119.8(1) . . . yes C4' N3' C10' 120.5(2) . . . yes Fe1' N4' N5' 137.9(1) . . . yes Fe1' N4' C9' 115.3(1) . . . yes N5' N4' C9' 106.1(1) . . . yes N4' N5' C7' 110.6(1) . . . yes N2' C1' C2' 108.4(2) . . . yes C1' C2' C3' 104.6(2) . . . yes N1' C3' C2' 110.4(2) . . . yes N1' C3' C4' 112.7(2) . . . yes C2' C3' C4' 136.6(2) . . . yes N3' C4' C3' 111.3(2) . . . yes N3' C4' C5' 121.2(2) . . . yes C3' C4' C5' 127.6(2) . . . yes C4' C5' C6' 118.1(2) . . . yes C5' C6' C11' 120.9(2) . . . yes N5' C7' C8' 108.4(2) . . . yes C7' C8' C9' 104.6(2) . . . yes N4' C9' C8' 110.4(2) . . . yes N4' C9' C10' 115.0(2) . . . yes C8' C9' C10' 134.4(2) . . . yes N3' C10' C9' 110.2(2) . . . yes N3' C10' C11' 121.2(2) . . . yes C9' C10' C11' 128.4(2) . . . yes C6' C11' C10' 118.1(2) . . . yes N1Np Fe2 C2Np 176.3(1) . . . yes N1Np Fe2 C3Np 98.3(1) . . . yes N1Np Fe2 C4Np 93.9(1) . . . yes N1Np Fe2 C5Np 91.7(1) . . . yes N1Np Fe2 C6Np 96.2(1) . . . yes C2Np Fe2 C3Np 85.4(1) . . . yes C2Np Fe2 C4Np 85.9(1) . . . yes C2Np Fe2 C5Np 84.6(1) . . . yes C2Np Fe2 C6Np 84.0(1) . . . yes C3Np Fe2 C4Np 88.2(1) . . . yes C3Np Fe2 C5Np 169.8(2) . . . yes C3Np Fe2 C6Np 89.6(1) . . . yes C4Np Fe2 C5Np 88.8(1) . . . yes C4Np Fe2 C6Np 169.9(2) . . . yes C5Np Fe2 C6Np 91.7(1) . . . yes Fe2 N1Np O1Np 168.2(3) . . . yes Fe2 N1Np O1Np1 168.2(3) . . . yes Fe2 N1Np O1Np2 168.2(3) . . . yes Fe2 N1Np O1Np3 168.2(3) . . . yes Fe2 N1Np O1Np3 168.2(3) . . . yes Fe2 C2Np N2Np 178.1(3) . . . yes Fe2 C3Np N3Np 177.1(2) . . . yes Fe2 C4Np N4Np 177.4(3) . . . yes Fe2 C5Np N5Np 178.8(4) . . . yes Fe2 C6Np N6Np 177.1(3) . . . yes N1 N2 N5Np 122.2(1) . . 3_655 yes C1 N2 N5Np 126.9(1) . . 3_655 yes N4 N5 N3Np 122.6(1) . . 2_565 yes C7 N5 N3Np 126.7(1) . . 2_565 yes N1' N2' N6Np 125.6(1) . . 3_655 yes C1' N2' N6Np 123.3(1) . . 3_655 yes N4' N5' N4Np 119.0(1) . . . yes C7' N5' N4Np 130.4(1) . . . yes N2 N5Np C5Np 118.7(2) 3_645 . . yes N5 N3Np C3Np 131.7(2) 2_565 . . yes N2' N6Np C6Np 129.4(3) 3_645 . . yes N5' N4Np C4Np 120.7 . . . yes N1 N2 HN2 124.7 . . . no C1 N2 HN2 124.7 . . . no N4 N5 HN5 124.7 . . . no C7 N5 HN5 124.7 . . . no N2 C1 HC1 125.8 . . . no C2 C1 HC1 125.8 . . . no C1 C2 HC2 127.7 . . . no C3 C2 HC2 127.7 . . . no C4 C5 HC5 120.9 . . . no C6 C5 HC5 120.9 . . . no C5 C6 HC6 119.6 . . . no C11 C6 HC6 119.6 . . . no N5 C7 HC7 125.8 . . . no C8 C7 HC7 125.8 . . . no C7 C8 HC8 127.7 . . . no C9 C8 HC8 127.7 . . . no C6 C11 HC11 120.9 . . . no C10 C11 HC11 120.9 . . . no N1' N2' HN2' 124.7 . . . no C1' N2' HN2' 124.7 . . . no N4' N5' HN5' 124.7 . . . no C7' N5' HN5' 124.7 . . . no N2' C1' HC1' 125.8 . . . no C2' C1' HC1' 125.8 . . . no C1' C2' HC2' 127.7 . . . no C3' C2' HC2' 127.7 . . . no C4' C5' HC5' 120.9 . . . no C6' C5' HC5' 120.9 . . . no C5' C6' HC6' 119.6 . . . no C11' C6' HC6' 119.6 . . . no N5' C7' HC7' 125.8 . . . no C8' C7' HC7' 125.8 . . . no C7' C8' HC8' 127.7 . . . no C9' C8' HC8' 127.7 . . . no C6' C11' HC11' 120.9 . . . no C10' C11' HC11' 120.9 . . . no