# Supplementary Material (ESI) for Soft Matter # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Soft Matter' _journal_coden_cambridge 0777 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name P.Sahoo P.Dastidar _publ_contact_author_name 'Pathik Sahoo' _publ_contact_author_email 2c.pathik@gmail.com data_1(5) _database_code_depnum_ccdc_archive 'CCDC 795748' #TrackingRef '- DASTIDAR_PS_FINAL CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration syn _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Fe O4, 2(C6 H16 N)' _chemical_formula_sum 'C24 H40 Fe N2 O4' _chemical_formula_weight 476.43 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' Fe Fe 0.3463 0.8444 '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' H H 0.0000 0.0000 '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 6.3577(13) _cell_length_b 9.6425(19) _cell_length_c 10.788(2) _cell_angle_alpha 91.280(4) _cell_angle_beta 103.763(4) _cell_angle_gamma 90.641(4) _cell_volume 642.1(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description NIDDLE _exptl_crystal_colour BROWN _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.617 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8661 _exptl_absorpt_correction_T_max 0.9353 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6194 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0854 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2259 _reflns_number_gt 1982 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.1000P)^2^+3.0485P] 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 2259 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1044 _refine_ls_R_factor_gt 0.0940 _refine_ls_wR_factor_ref 0.2255 _refine_ls_wR_factor_gt 0.2173 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 1.0000 1.0000 0.0270(4) Uani 1 2 d S . . O2 O 0.3035(8) 0.6401(5) 0.9083(6) 0.0646(15) Uani 1 1 d . . . O3 O 0.0134(8) 0.7527(5) 0.9322(6) 0.0716(16) Uani 1 1 d . . . C4 C 0.1963(11) 0.7487(8) 0.9057(7) 0.0540(18) Uani 1 1 d . . . C5 C 0.2855(10) 0.8814(7) 0.8708(6) 0.0469(16) Uani 1 1 d . . . C6 C 0.1986(11) 1.0137(8) 0.8806(7) 0.060(2) Uani 1 1 d . . . H6 H 0.0644 1.0333 0.9069 0.072 Uiso 1 1 calc R . . C7 C 0.3421(13) 1.1141(8) 0.8503(8) 0.064(2) Uani 1 1 d . . . H7 H 0.3239 1.2149 0.8508 0.076 Uiso 1 1 calc R . . C8 C 0.5164(13) 1.0417(9) 0.8178(7) 0.064(2) Uani 1 1 d . . . H8 H 0.6402 1.0843 0.7927 0.076 Uiso 1 1 calc R . . C9 C 0.4828(11) 0.8991(8) 0.8302(7) 0.0540(18) Uani 1 1 d . . . H9 H 0.5778 0.8248 0.8145 0.065 Uiso 1 1 calc R . . N10 N 0.7074(9) 0.5506(6) 0.9049(6) 0.0605(17) Uani 1 1 d . . . H10A H 0.8214 0.6079 0.9157 0.091 Uiso 1 1 calc R . . H10B H 0.7354 0.4847 0.9627 0.091 Uiso 1 1 calc R . . H10C H 0.5925 0.5979 0.9142 0.091 Uiso 1 1 calc R . . C11 C 0.6619(15) 0.4855(11) 0.7739(11) 0.091(3) Uani 1 1 d . . . H11A H 0.5405 0.4210 0.7640 0.109 Uiso 1 1 calc R . . H11B H 0.6200 0.5572 0.7116 0.109 Uiso 1 1 calc R . . C12 C 0.8463(15) 0.4119(11) 0.7475(10) 0.087(3) Uani 1 1 d . . . H12A H 0.8822 0.3359 0.8058 0.104 Uiso 1 1 calc R . . H12B H 0.9706 0.4747 0.7624 0.104 Uiso 1 1 calc R . . C13 C 0.799(2) 0.3544(13) 0.6092(10) 0.107(4) Uani 1 1 d . . . H13A H 0.6811 0.2869 0.5961 0.128 Uiso 1 1 calc R . . H13B H 0.7532 0.4295 0.5510 0.128 Uiso 1 1 calc R . . C14 C 0.994(2) 0.2872(14) 0.5790(11) 0.113(4) Uani 1 1 d . . . H14A H 1.1127 0.3543 0.5962 0.136 Uiso 1 1 calc R . . H14B H 1.0361 0.2108 0.6362 0.136 Uiso 1 1 calc R . . C15 C 0.963(2) 0.2351(14) 0.4490(10) 0.118(4) Uani 1 1 d . . . H15A H 0.9265 0.3114 0.3911 0.141 Uiso 1 1 calc R . . H15B H 0.8425 0.1692 0.4302 0.141 Uiso 1 1 calc R . . C16 C 1.162(2) 0.1654(16) 0.4268(14) 0.141(5) Uani 1 1 d . . . H16A H 1.2057 0.0948 0.4886 0.211 Uiso 1 1 calc R . . H16B H 1.2770 0.2329 0.4351 0.211 Uiso 1 1 calc R . . H16C H 1.1303 0.1240 0.3425 0.211 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0131(5) 0.0289(6) 0.0359(7) 0.0052(5) -0.0007(4) -0.0026(4) O2 0.041(3) 0.055(3) 0.099(4) 0.001(3) 0.021(3) -0.002(2) O3 0.037(3) 0.064(3) 0.120(5) -0.004(3) 0.031(3) -0.012(2) C4 0.040(4) 0.060(5) 0.056(4) -0.002(4) 0.000(3) -0.009(3) C5 0.031(3) 0.054(4) 0.047(4) -0.001(3) -0.005(3) -0.012(3) C6 0.037(4) 0.067(5) 0.063(5) 0.010(4) -0.013(3) 0.003(3) C7 0.062(5) 0.050(4) 0.066(5) 0.019(4) -0.012(4) 0.000(4) C8 0.055(5) 0.082(6) 0.051(5) 0.015(4) 0.006(4) -0.019(4) C9 0.044(4) 0.058(4) 0.059(5) -0.005(4) 0.012(3) -0.009(3) N10 0.040(3) 0.061(4) 0.084(5) 0.004(3) 0.021(3) -0.007(3) C11 0.058(5) 0.099(7) 0.112(8) -0.018(6) 0.013(5) -0.003(5) C12 0.063(6) 0.104(7) 0.090(7) 0.005(6) 0.012(5) -0.007(5) C13 0.108(9) 0.126(10) 0.083(8) -0.012(7) 0.018(7) -0.015(7) C14 0.107(9) 0.131(10) 0.087(8) -0.003(7) -0.002(7) -0.001(8) C15 0.133(11) 0.143(11) 0.066(7) -0.007(7) 0.003(7) -0.010(9) C16 0.108(10) 0.178(14) 0.131(12) -0.011(10) 0.018(9) 0.026(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C5 2.024(6) . ? Fe1 C5 2.024(6) 2_677 ? Fe1 C9 2.034(7) . ? Fe1 C9 2.034(7) 2_677 ? Fe1 C8 2.041(7) . ? Fe1 C8 2.041(7) 2_677 ? Fe1 C6 2.046(7) . ? Fe1 C6 2.046(7) 2_677 ? Fe1 C7 2.039(7) . ? Fe1 C7 2.039(7) 2_677 ? O2 O2 0.000(10) 1 ? O2 C4 1.253(8) . ? O3 C4 1.263(9) . ? C4 O2 1.253(8) 1 ? C4 C5 1.486(10) . ? C5 C6 1.407(10) . ? C5 C9 1.433(9) . ? C6 C7 1.419(11) . ? C6 H6 0.9800 . ? C7 C8 1.425(12) . ? C7 H7 0.9800 . ? C8 C9 1.404(10) . ? C8 H8 0.9800 . ? C9 H9 0.9800 . ? N10 C11 1.495(11) . ? N10 H10A 0.8900 . ? N10 H10B 0.8900 . ? N10 H10C 0.8900 . ? C11 C12 1.458(13) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.539(14) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.504(16) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.446(14) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.506(17) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Fe1 C5 180.000(2) . 2_677 ? C5 Fe1 C9 41.4(3) . . ? C5 Fe1 C9 138.6(3) 2_677 . ? C5 Fe1 C9 138.6(3) . 2_677 ? C5 Fe1 C9 41.4(3) 2_677 2_677 ? C9 Fe1 C9 180.000(3) . 2_677 ? C5 Fe1 C8 68.7(3) . . ? C5 Fe1 C8 111.3(3) 2_677 . ? C9 Fe1 C8 40.3(3) . . ? C9 Fe1 C8 139.7(3) 2_677 . ? C5 Fe1 C8 111.3(3) . 2_677 ? C5 Fe1 C8 68.7(3) 2_677 2_677 ? C9 Fe1 C8 139.7(3) . 2_677 ? C9 Fe1 C8 40.3(3) 2_677 2_677 ? C8 Fe1 C8 180.000(4) . 2_677 ? C5 Fe1 C6 40.4(3) . . ? C5 Fe1 C6 139.6(3) 2_677 . ? C9 Fe1 C6 68.5(3) . . ? C9 Fe1 C6 111.5(3) 2_677 . ? C8 Fe1 C6 68.3(3) . . ? C8 Fe1 C6 111.7(3) 2_677 . ? C5 Fe1 C6 139.6(3) . 2_677 ? C5 Fe1 C6 40.4(3) 2_677 2_677 ? C9 Fe1 C6 111.5(3) . 2_677 ? C9 Fe1 C6 68.5(3) 2_677 2_677 ? C8 Fe1 C6 111.7(3) . 2_677 ? C8 Fe1 C6 68.3(3) 2_677 2_677 ? C6 Fe1 C6 180.000(2) . 2_677 ? C5 Fe1 C7 68.7(3) . . ? C5 Fe1 C7 111.3(3) 2_677 . ? C9 Fe1 C7 68.5(3) . . ? C9 Fe1 C7 111.5(3) 2_677 . ? C8 Fe1 C7 40.9(3) . . ? C8 Fe1 C7 139.1(3) 2_677 . ? C6 Fe1 C7 40.7(3) . . ? C6 Fe1 C7 139.3(3) 2_677 . ? C5 Fe1 C7 111.3(3) . 2_677 ? C5 Fe1 C7 68.7(3) 2_677 2_677 ? C9 Fe1 C7 111.5(3) . 2_677 ? C9 Fe1 C7 68.5(3) 2_677 2_677 ? C8 Fe1 C7 139.1(3) . 2_677 ? C8 Fe1 C7 40.9(3) 2_677 2_677 ? C6 Fe1 C7 139.3(3) . 2_677 ? C6 Fe1 C7 40.7(3) 2_677 2_677 ? C7 Fe1 C7 180.000(3) . 2_677 ? O2 C4 O3 123.4(7) 1 . ? O2 C4 O3 123.4(7) . . ? O2 C4 C5 119.6(6) 1 . ? O2 C4 C5 119.6(6) . . ? O3 C4 C5 117.0(7) . . ? C6 C5 C9 107.8(6) . . ? C6 C5 C4 125.8(7) . . ? C9 C5 C4 126.3(7) . . ? C6 C5 Fe1 70.6(4) . . ? C9 C5 Fe1 69.7(4) . . ? C4 C5 Fe1 121.9(5) . . ? C5 C6 C7 108.4(7) . . ? C5 C6 Fe1 68.9(4) . . ? C7 C6 Fe1 69.4(4) . . ? C5 C6 H6 125.8 . . ? C7 C6 H6 125.8 . . ? Fe1 C6 H6 125.8 . . ? C6 C7 C8 107.5(7) . . ? C6 C7 Fe1 69.9(4) . . ? C8 C7 Fe1 69.6(4) . . ? C6 C7 H7 126.2 . . ? C8 C7 H7 126.2 . . ? Fe1 C7 H7 126.2 . . ? C9 C8 C7 108.4(7) . . ? C9 C8 Fe1 69.6(4) . . ? C7 C8 Fe1 69.5(4) . . ? C9 C8 H8 125.8 . . ? C7 C8 H8 125.8 . . ? Fe1 C8 H8 125.8 . . ? C8 C9 C5 107.9(7) . . ? C8 C9 Fe1 70.1(4) . . ? C5 C9 Fe1 69.0(4) . . ? C8 C9 H9 126.1 . . ? C5 C9 H9 126.1 . . ? Fe1 C9 H9 126.1 . . ? C11 N10 H10A 109.5 . . ? C11 N10 H10B 109.5 . . ? H10A N10 H10B 109.5 . . ? C11 N10 H10C 109.5 . . ? H10A N10 H10C 109.5 . . ? H10B N10 H10C 109.5 . . ? C12 C11 N10 113.3(8) . . ? C12 C11 H11A 108.9 . . ? N10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? N10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 112.0(9) . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 112.1(10) . . ? C14 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? C14 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C15 C14 C13 115.0(11) . . ? C15 C14 H14A 108.5 . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14B 108.5 . . ? C13 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C14 C15 C16 112.1(11) . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10A O3 0.89 1.82 2.700(8) 168.3 1_655 N10 H10B O2 0.89 1.92 2.770(8) 160.0 2_667 N10 H10C O2 0.89 1.87 2.727(8) 160.0 1 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.255 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.124 # Attachment '1(9)_ps0721p.cif' data_ps0721p _database_code_depnum_ccdc_archive 'CCDC 795749' #TrackingRef '1(9)_ps0721p.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration syn _chemical_melting_point ? _chemical_formula_moiety '2(C10 H24 N), C12 H8 Fe O4' _chemical_formula_sum 'C32 H56 Fe N2 O4' _chemical_formula_weight 588.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 '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' _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 6.344(3) _cell_length_b 9.743(5) _cell_length_c 13.824(7) _cell_angle_alpha 101.950(7) _cell_angle_beta 92.720(8) _cell_angle_gamma 91.480(8) _cell_volume 834.4(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description NIDDLE _exptl_crystal_colour BROWN _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.487 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8921 _exptl_absorpt_correction_T_max 0.9484 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9015 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2933 _reflns_number_gt 2803 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0561P)^2^+0.2563P] 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 2933 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1147 _refine_ls_wR_factor_gt 0.1131 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.0000 0.0000 0.5000 0.03958(17) Uani 1 2 d S . . O2 O 0.4561(3) 0.22729(19) 0.44587(16) 0.0646(5) Uani 1 1 d . . . O3 O 0.1566(2) 0.33380(17) 0.43203(13) 0.0537(4) Uani 1 1 d . . . C4 C 0.2625(3) 0.2251(2) 0.42765(16) 0.0445(5) Uani 1 1 d . . . C5 C 0.1502(3) 0.0859(2) 0.39950(16) 0.0433(5) Uani 1 1 d . . . C6 C -0.0682(4) 0.0585(3) 0.36939(17) 0.0511(6) Uani 1 1 d . . . H6 H -0.1701 0.1283 0.3583 0.061 Uiso 1 1 calc R . . C7 C -0.1111(5) -0.0866(3) 0.35913(19) 0.0613(7) Uani 1 1 d . . . H7 H -0.2487 -0.1352 0.3402 0.074 Uiso 1 1 calc R . . C8 C 0.0775(5) -0.1495(3) 0.3830(2) 0.0630(7) Uani 1 1 d . . . H8 H 0.0932 -0.2493 0.3829 0.076 Uiso 1 1 calc R . . C9 C 0.2391(4) -0.0442(2) 0.40642(18) 0.0517(6) Uani 1 1 d . . . H9 H 0.3864 -0.0580 0.4257 0.062 Uiso 1 1 calc R . . N10 N 0.7529(3) 0.4218(2) 0.42772(15) 0.0522(5) Uani 1 1 d . . . H10A H 0.7558 0.5021 0.4724 0.078 Uiso 1 1 calc R . . H10B H 0.8708 0.3766 0.4352 0.078 Uiso 1 1 calc R . . H10C H 0.6418 0.3686 0.4361 0.078 Uiso 1 1 calc R . . C11 C 0.7366(4) 0.4520(3) 0.3267(2) 0.0644(7) Uani 1 1 d . . . H11A H 0.7408 0.3646 0.2783 0.077 Uiso 1 1 calc R . . H11B H 0.8572 0.5107 0.3182 0.077 Uiso 1 1 calc R . . C12 C 0.5388(4) 0.5240(3) 0.3080(2) 0.0609(7) Uani 1 1 d . . . H12A H 0.5364 0.6124 0.3555 0.073 Uiso 1 1 calc R . . H12B H 0.4184 0.4663 0.3183 0.073 Uiso 1 1 calc R . . C13 C 0.5183(5) 0.5520(3) 0.2039(2) 0.0677(7) Uani 1 1 d . . . H13A H 0.6358 0.6129 0.1947 0.081 Uiso 1 1 calc R . . H13B H 0.5268 0.4640 0.1565 0.081 Uiso 1 1 calc R . . C14 C 0.3163(5) 0.6188(4) 0.1836(2) 0.0734(8) Uani 1 1 d . . . H14A H 0.3108 0.7074 0.2306 0.088 Uiso 1 1 calc R . . H14B H 0.2002 0.5589 0.1958 0.088 Uiso 1 1 calc R . . C15 C 0.2813(5) 0.6461(3) 0.0808(2) 0.0718(8) Uani 1 1 d . . . H15A H 0.2872 0.5580 0.0332 0.086 Uiso 1 1 calc R . . H15B H 0.3951 0.7076 0.0685 0.086 Uiso 1 1 calc R . . C16 C 0.0732(5) 0.7119(4) 0.0641(2) 0.0753(8) Uani 1 1 d . . . H16A H -0.0400 0.6484 0.0743 0.090 Uiso 1 1 calc R . . H16B H 0.0654 0.7976 0.1139 0.090 Uiso 1 1 calc R . . C17 C 0.0354(5) 0.7463(4) -0.0365(2) 0.0758(8) Uani 1 1 d . . . H17A H 0.0414 0.6606 -0.0864 0.091 Uiso 1 1 calc R . . H17B H 0.1488 0.8094 -0.0471 0.091 Uiso 1 1 calc R . . C18 C -0.1723(5) 0.8129(4) -0.0511(2) 0.0770(8) Uani 1 1 d . . . H18A H -0.2855 0.7490 -0.0416 0.092 Uiso 1 1 calc R . . H18B H -0.1792 0.8976 -0.0003 0.092 Uiso 1 1 calc R . . C19 C -0.2105(6) 0.8503(4) -0.1505(2) 0.0842(9) Uani 1 1 d . . . H19A H -0.2051 0.7657 -0.2015 0.101 Uiso 1 1 calc R . . H19B H -0.0975 0.9141 -0.1603 0.101 Uiso 1 1 calc R . . C20 C -0.4188(6) 0.9175(5) -0.1629(3) 0.1002(12) Uani 1 1 d . . . H20A H -0.5321 0.8545 -0.1546 0.150 Uiso 1 1 calc R . . H20B H -0.4330 0.9378 -0.2279 0.150 Uiso 1 1 calc R . . H20C H -0.4239 1.0031 -0.1142 0.150 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0396(3) 0.0295(3) 0.0486(3) 0.00335(18) 0.01556(18) -0.00311(17) O2 0.0329(9) 0.0577(11) 0.1078(15) 0.0299(10) -0.0008(9) -0.0060(7) O3 0.0410(9) 0.0414(9) 0.0798(11) 0.0160(8) 0.0020(8) -0.0029(7) C4 0.0376(12) 0.0472(13) 0.0515(12) 0.0167(10) 0.0056(9) -0.0043(10) C5 0.0395(12) 0.0441(13) 0.0476(12) 0.0115(10) 0.0116(9) -0.0044(9) C6 0.0464(13) 0.0540(15) 0.0523(13) 0.0118(11) -0.0005(10) -0.0081(11) C7 0.0657(17) 0.0562(16) 0.0547(14) -0.0038(12) 0.0098(12) -0.0234(13) C8 0.084(2) 0.0375(13) 0.0648(16) -0.0027(11) 0.0342(14) -0.0029(13) C9 0.0485(13) 0.0465(14) 0.0626(14) 0.0109(11) 0.0261(11) 0.0099(11) N10 0.0365(10) 0.0483(12) 0.0717(13) 0.0135(10) 0.0006(9) -0.0040(8) C11 0.0525(15) 0.0671(18) 0.0748(18) 0.0167(14) 0.0117(13) -0.0019(13) C12 0.0586(16) 0.0628(17) 0.0623(15) 0.0136(13) 0.0102(12) 0.0010(13) C13 0.0732(19) 0.0730(19) 0.0592(16) 0.0166(14) 0.0128(13) 0.0043(15) C14 0.085(2) 0.082(2) 0.0557(15) 0.0170(14) 0.0157(14) 0.0120(17) C15 0.084(2) 0.075(2) 0.0581(16) 0.0168(14) 0.0163(14) 0.0072(16) C16 0.083(2) 0.081(2) 0.0641(17) 0.0169(15) 0.0151(15) 0.0064(17) C17 0.086(2) 0.079(2) 0.0667(17) 0.0223(15) 0.0159(15) 0.0036(17) C18 0.081(2) 0.083(2) 0.0694(18) 0.0197(16) 0.0117(15) -0.0006(17) C19 0.092(2) 0.092(2) 0.0717(19) 0.0248(17) 0.0112(17) 0.0042(19) C20 0.097(3) 0.119(3) 0.089(2) 0.032(2) 0.001(2) 0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C5 2.026(2) 2_556 ? Fe1 C5 2.026(2) . ? Fe1 C8 2.029(2) . ? Fe1 C8 2.029(2) 2_556 ? Fe1 C6 2.034(3) . ? Fe1 C6 2.034(3) 2_556 ? Fe1 C9 2.037(2) . ? Fe1 C9 2.037(2) 2_556 ? Fe1 C7 2.039(3) . ? Fe1 C7 2.039(3) 2_556 ? O2 O2 0.000(5) 1 ? O2 C4 1.241(3) . ? O3 C4 1.261(3) . ? C4 O2 1.241(3) 1 ? C4 C5 1.484(3) . ? C5 C9 1.420(3) . ? C5 C6 1.430(3) . ? C6 C7 1.409(4) . ? C6 H6 0.9800 . ? C7 C8 1.414(4) . ? C7 H7 0.9800 . ? C8 C9 1.409(4) . ? C8 H8 0.9800 . ? C9 H9 0.9800 . ? N10 C11 1.485(3) . ? N10 H10A 0.8900 . ? N10 H10B 0.8900 . ? N10 H10C 0.8900 . ? C11 C12 1.491(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.520(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.493(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.507(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.511(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.507(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.507(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.503(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.508(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Fe1 C5 180.000(1) 2_556 . ? C5 Fe1 C8 111.23(10) 2_556 . ? C5 Fe1 C8 68.77(10) . . ? C5 Fe1 C8 68.77(10) 2_556 2_556 ? C5 Fe1 C8 111.23(10) . 2_556 ? C8 Fe1 C8 180.00(11) . 2_556 ? C5 Fe1 C6 138.76(9) 2_556 . ? C5 Fe1 C6 41.24(9) . . ? C8 Fe1 C6 68.54(12) . . ? C8 Fe1 C6 111.46(12) 2_556 . ? C5 Fe1 C6 41.24(9) 2_556 2_556 ? C5 Fe1 C6 138.76(9) . 2_556 ? C8 Fe1 C6 111.46(12) . 2_556 ? C8 Fe1 C6 68.54(12) 2_556 2_556 ? C6 Fe1 C6 180.000(1) . 2_556 ? C5 Fe1 C9 139.09(9) 2_556 . ? C5 Fe1 C9 40.91(9) . . ? C8 Fe1 C9 40.56(10) . . ? C8 Fe1 C9 139.44(10) 2_556 . ? C6 Fe1 C9 68.74(11) . . ? C6 Fe1 C9 111.26(11) 2_556 . ? C5 Fe1 C9 40.91(9) 2_556 2_556 ? C5 Fe1 C9 139.09(9) . 2_556 ? C8 Fe1 C9 139.44(10) . 2_556 ? C8 Fe1 C9 40.56(10) 2_556 2_556 ? C6 Fe1 C9 111.26(11) . 2_556 ? C6 Fe1 C9 68.74(11) 2_556 2_556 ? C9 Fe1 C9 180.000(1) . 2_556 ? C5 Fe1 C7 111.29(10) 2_556 . ? C5 Fe1 C7 68.71(10) . . ? C8 Fe1 C7 40.67(12) . . ? C8 Fe1 C7 139.33(12) 2_556 . ? C6 Fe1 C7 40.48(11) . . ? C6 Fe1 C7 139.52(11) 2_556 . ? C9 Fe1 C7 68.30(11) . . ? C9 Fe1 C7 111.70(11) 2_556 . ? C5 Fe1 C7 68.71(10) 2_556 2_556 ? C5 Fe1 C7 111.29(10) . 2_556 ? C8 Fe1 C7 139.33(12) . 2_556 ? C8 Fe1 C7 40.67(12) 2_556 2_556 ? C6 Fe1 C7 139.52(11) . 2_556 ? C6 Fe1 C7 40.48(11) 2_556 2_556 ? C9 Fe1 C7 111.70(11) . 2_556 ? C9 Fe1 C7 68.30(11) 2_556 2_556 ? C7 Fe1 C7 180.0 . 2_556 ? O2 C4 O3 123.9(2) 1 . ? O2 C4 O3 123.9(2) . . ? O2 C4 C5 117.6(2) 1 . ? O2 C4 C5 117.6(2) . . ? O3 C4 C5 118.5(2) . . ? C9 C5 C6 107.5(2) . . ? C9 C5 C4 125.2(2) . . ? C6 C5 C4 127.1(2) . . ? C9 C5 Fe1 69.95(12) . . ? C6 C5 Fe1 69.67(13) . . ? C4 C5 Fe1 121.62(15) . . ? C7 C6 C5 107.8(2) . . ? C7 C6 Fe1 69.97(15) . . ? C5 C6 Fe1 69.09(13) . . ? C7 C6 H6 126.1 . . ? C5 C6 H6 126.1 . . ? Fe1 C6 H6 126.1 . . ? C6 C7 C8 108.3(2) . . ? C6 C7 Fe1 69.55(14) . . ? C8 C7 Fe1 69.28(15) . . ? C6 C7 H7 125.9 . . ? C8 C7 H7 125.9 . . ? Fe1 C7 H7 125.9 . . ? C9 C8 C7 108.3(2) . . ? C9 C8 Fe1 70.01(13) . . ? C7 C8 Fe1 70.05(14) . . ? C9 C8 H8 125.9 . . ? C7 C8 H8 125.9 . . ? Fe1 C8 H8 125.9 . . ? C8 C9 C5 108.1(2) . . ? C8 C9 Fe1 69.43(13) . . ? C5 C9 Fe1 69.14(12) . . ? C8 C9 H9 125.9 . . ? C5 C9 H9 125.9 . . ? Fe1 C9 H9 125.9 . . ? C11 N10 H10A 109.5 . . ? C11 N10 H10B 109.5 . . ? H10A N10 H10B 109.5 . . ? C11 N10 H10C 109.5 . . ? H10A N10 H10C 109.5 . . ? H10B N10 H10C 109.5 . . ? N10 C11 C12 112.4(2) . . ? N10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? N10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 112.7(2) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 112.8(2) . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 116.0(2) . . ? C13 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? C13 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C14 C15 C16 113.7(2) . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15B 108.8 . . ? C16 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 115.4(2) . . ? C17 C16 H16A 108.4 . . ? C15 C16 H16A 108.4 . . ? C17 C16 H16B 108.4 . . ? C15 C16 H16B 108.4 . . ? H16A C16 H16B 107.5 . . ? C16 C17 C18 114.5(2) . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17B 108.6 . . ? C18 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C19 C18 C17 115.1(3) . . ? C19 C18 H18A 108.5 . . ? C17 C18 H18A 108.5 . . ? C19 C18 H18B 108.5 . . ? C17 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C18 C19 C20 114.0(3) . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10A O3 0.89 1.90 2.770(3) 164.2 2_666 N10 H10B O3 0.89 1.87 2.724(3) 159.6 1_655 N10 H10C O2 0.89 1.82 2.694(3) 166.9 1 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.466 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.060 # Attachment '1(11)_pso727l.cif' data_pso727l _database_code_depnum_ccdc_archive 'CCDC 795750' #TrackingRef '1(11)_pso727l.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C12 H28 N), C12 H8 Fe O4' _chemical_formula_sum 'C36 H64 Fe N2 O4' _chemical_formula_weight 644.74 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' Fe Fe 0.3463 0.8444 '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' H H 0.0000 0.0000 '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 6.3523(10) _cell_length_b 9.7708(15) _cell_length_c 15.689(3) _cell_angle_alpha 74.333(3) _cell_angle_beta 86.777(3) _cell_angle_gamma 88.341(3) _cell_volume 936.0(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description NIDDLE _exptl_crystal_colour BROWN _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.439 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8758 _exptl_absorpt_correction_T_max 0.9330 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9154 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3298 _reflns_number_gt 2859 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.1000P)^2^+0.3275P] 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 3298 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 0.859 _refine_ls_restrained_S_all 0.859 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 0.5000 0.0000 0.0454(2) Uani 1 2 d S . . O2 O 0.0320(3) 0.7220(2) 0.04878(16) 0.0718(6) Uani 1 1 d . . . O3 O 0.3285(3) 0.82727(19) 0.06090(13) 0.0603(5) Uani 1 1 d . . . C4 C 0.2211(4) 0.7183(3) 0.06510(17) 0.0500(6) Uani 1 1 d . . . C5 C 0.3279(4) 0.5764(3) 0.09023(16) 0.0482(6) Uani 1 1 d . . . C9 C 0.2408(4) 0.4474(3) 0.08384(18) 0.0586(7) Uani 1 1 d . . . H9 H 0.0978 0.4354 0.0667 0.070 Uiso 1 1 calc R . . C6 C 0.5384(4) 0.5458(3) 0.11677(18) 0.0578(6) Uani 1 1 d . . . H6 H 0.6377 0.6142 0.1266 0.069 Uiso 1 1 calc R . . C8 C 0.3972(5) 0.3403(3) 0.1052(2) 0.0704(9) Uani 1 1 d . . . H8 H 0.3819 0.2407 0.1054 0.084 Uiso 1 1 calc R . . C7 C 0.5796(5) 0.4007(3) 0.12596(19) 0.0687(8) Uani 1 1 d . . . H7 H 0.7129 0.3504 0.1430 0.082 Uiso 1 1 calc R . . N10 N -0.2696(3) -0.0850(2) 0.06437(16) 0.0591(6) Uani 1 1 d . . . H10A H -0.2630 -0.0008 0.0244 0.089 Uiso 1 1 calc R . . H10B H -0.3853 -0.1295 0.0576 0.089 Uiso 1 1 calc R . . H10C H -0.1564 -0.1372 0.0569 0.089 Uiso 1 1 calc R . . C19 C 0.5656(5) 0.2883(4) 0.5814(2) 0.0815(9) Uani 1 1 d . . . H19A H 0.4507 0.3515 0.5900 0.098 Uiso 1 1 calc R . . H19B H 0.5472 0.1991 0.6267 0.098 Uiso 1 1 calc R . . C21 C 0.7861(6) 0.3810(4) 0.6835(2) 0.0895(10) Uani 1 1 d . . . H21A H 0.7690 0.2922 0.7293 0.107 Uiso 1 1 calc R . . H21B H 0.6711 0.4442 0.6921 0.107 Uiso 1 1 calc R . . C11 C -0.2763(5) -0.0643(4) 0.1545(2) 0.0709(8) Uani 1 1 d . . . H11A H -0.2917 -0.1558 0.1978 0.085 Uiso 1 1 calc R . . H11B H -0.3985 -0.0060 0.1620 0.085 Uiso 1 1 calc R . . C12 C -0.0818(5) 0.0053(3) 0.1712(2) 0.0675(8) Uani 1 1 d . . . H12A H -0.0683 0.0976 0.1286 0.081 Uiso 1 1 calc R . . H12B H 0.0405 -0.0519 0.1623 0.081 Uiso 1 1 calc R . . C13 C -0.0844(5) 0.0243(4) 0.2643(2) 0.0740(8) Uani 1 1 d . . . H13A H -0.2035 0.0847 0.2725 0.089 Uiso 1 1 calc R . . H13B H -0.1035 -0.0675 0.3070 0.089 Uiso 1 1 calc R . . C17 C 0.3440(5) 0.1977(4) 0.4776(2) 0.0787(9) Uani 1 1 d . . . H17A H 0.3242 0.1081 0.5224 0.094 Uiso 1 1 calc R . . H17B H 0.2294 0.2611 0.4862 0.094 Uiso 1 1 calc R . . C15 C 0.1247(5) 0.1082(4) 0.3736(2) 0.0750(8) Uani 1 1 d . . . H15A H 0.1074 0.0166 0.4167 0.090 Uiso 1 1 calc R . . H15B H 0.0086 0.1693 0.3839 0.090 Uiso 1 1 calc R . . C18 C 0.5496(5) 0.2608(4) 0.4918(2) 0.0799(9) Uani 1 1 d . . . H18A H 0.6639 0.1969 0.4835 0.096 Uiso 1 1 calc R . . H18B H 0.5697 0.3499 0.4465 0.096 Uiso 1 1 calc R . . C16 C 0.3295(5) 0.1719(4) 0.3881(2) 0.0783(9) Uani 1 1 d . . . H16A H 0.4446 0.1089 0.3794 0.094 Uiso 1 1 calc R . . H16B H 0.3487 0.2616 0.3433 0.094 Uiso 1 1 calc R . . C14 C 0.1136(5) 0.0887(4) 0.2821(2) 0.0777(9) Uani 1 1 d . . . H14A H 0.1303 0.1808 0.2395 0.093 Uiso 1 1 calc R . . H14B H 0.2319 0.0291 0.2719 0.093 Uiso 1 1 calc R . . C20 C 0.7701(5) 0.3524(4) 0.5942(2) 0.0812(9) Uani 1 1 d . . . H20A H 0.7889 0.4412 0.5486 0.097 Uiso 1 1 calc R . . H20B H 0.8848 0.2888 0.5860 0.097 Uiso 1 1 calc R . . C22 C 0.9919(6) 0.4465(5) 0.6948(3) 0.1062(13) Uani 1 1 d . . . H22A H 1.1070 0.3851 0.6861 0.159 Uiso 1 1 calc R . . H22B H 0.9928 0.4589 0.7534 0.159 Uiso 1 1 calc R . . H22C H 1.0065 0.5373 0.6519 0.159 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0427(3) 0.0355(3) 0.0542(3) -0.0087(2) 0.0127(2) 0.00261(19) O2 0.0399(10) 0.0699(12) 0.1156(17) -0.0419(12) -0.0122(10) 0.0117(9) O3 0.0462(10) 0.0503(10) 0.0885(13) -0.0257(9) -0.0064(9) 0.0040(8) C4 0.0405(13) 0.0561(15) 0.0572(15) -0.0228(12) 0.0005(11) 0.0053(11) C5 0.0419(12) 0.0506(14) 0.0520(14) -0.0163(11) 0.0081(10) 0.0049(10) C9 0.0511(14) 0.0535(15) 0.0694(17) -0.0171(13) 0.0207(12) -0.0088(12) C6 0.0535(15) 0.0584(16) 0.0605(16) -0.0154(12) -0.0030(12) 0.0097(12) C8 0.088(2) 0.0406(14) 0.0706(18) -0.0025(12) 0.0330(16) -0.0005(14) C7 0.0695(18) 0.0610(17) 0.0624(17) 0.0014(13) 0.0084(14) 0.0237(15) N10 0.0431(11) 0.0566(13) 0.0800(16) -0.0222(11) -0.0068(10) 0.0066(10) C19 0.080(2) 0.092(2) 0.074(2) -0.0290(18) 0.0058(16) -0.0010(18) C21 0.093(3) 0.103(3) 0.076(2) -0.032(2) 0.0020(18) -0.001(2) C11 0.0599(17) 0.076(2) 0.079(2) -0.0254(16) 0.0059(14) 0.0026(15) C12 0.0629(17) 0.0725(19) 0.0676(18) -0.0216(15) 0.0055(14) -0.0011(14) C13 0.078(2) 0.079(2) 0.0651(18) -0.0223(16) 0.0095(15) -0.0029(16) C17 0.081(2) 0.091(2) 0.067(2) -0.0285(17) 0.0093(16) -0.0044(18) C15 0.083(2) 0.082(2) 0.0596(17) -0.0216(15) 0.0114(15) -0.0073(17) C18 0.079(2) 0.089(2) 0.074(2) -0.0284(18) 0.0051(16) 0.0004(18) C16 0.082(2) 0.084(2) 0.0686(19) -0.0235(16) 0.0110(16) -0.0055(17) C14 0.080(2) 0.092(2) 0.0621(18) -0.0248(16) 0.0126(15) -0.0127(18) C20 0.082(2) 0.091(2) 0.071(2) -0.0260(18) 0.0035(16) 0.0049(18) C22 0.100(3) 0.134(4) 0.093(3) -0.043(3) -0.009(2) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C5 2.026(2) 2_665 ? Fe1 C5 2.026(2) . ? Fe1 C6 2.029(3) 2_665 ? Fe1 C6 2.029(3) . ? Fe1 C8 2.033(3) . ? Fe1 C8 2.033(3) 2_665 ? Fe1 C9 2.036(2) . ? Fe1 C9 2.036(2) 2_665 ? Fe1 C7 2.037(3) . ? Fe1 C7 2.037(3) 2_665 ? O2 C4 1.240(3) . ? O3 C4 1.266(3) . ? C4 C5 1.490(3) . ? C5 C9 1.421(4) . ? C5 C6 1.422(4) . ? C9 C8 1.408(4) . ? C9 H9 0.9800 . ? C6 C7 1.405(4) . ? C6 H6 0.9800 . ? C8 C7 1.408(5) . ? C8 H8 0.9800 . ? C7 H7 0.9800 . ? N10 C11 1.480(4) . ? N10 H10A 0.8900 . ? N10 H10B 0.8900 . ? N10 H10C 0.8900 . ? C19 C20 1.505(5) . ? C19 C18 1.510(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C21 C20 1.510(5) . ? C21 C22 1.511(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C11 C12 1.497(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.520(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.495(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C17 C16 1.499(4) . ? C17 C18 1.513(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C15 C14 1.504(4) . ? C15 C16 1.513(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Fe1 C5 180.000(1) 2_665 . ? C5 Fe1 C6 41.07(10) 2_665 2_665 ? C5 Fe1 C6 138.93(10) . 2_665 ? C5 Fe1 C6 138.93(10) 2_665 . ? C5 Fe1 C6 41.07(10) . . ? C6 Fe1 C6 180.00(14) 2_665 . ? C5 Fe1 C8 111.41(10) 2_665 . ? C5 Fe1 C8 68.59(10) . . ? C6 Fe1 C8 111.77(13) 2_665 . ? C6 Fe1 C8 68.23(13) . . ? C5 Fe1 C8 68.59(10) 2_665 2_665 ? C5 Fe1 C8 111.41(10) . 2_665 ? C6 Fe1 C8 68.23(13) 2_665 2_665 ? C6 Fe1 C8 111.77(13) . 2_665 ? C8 Fe1 C8 180.0(2) . 2_665 ? C5 Fe1 C9 139.05(10) 2_665 . ? C5 Fe1 C9 40.95(10) . . ? C6 Fe1 C9 111.39(12) 2_665 . ? C6 Fe1 C9 68.61(11) . . ? C8 Fe1 C9 40.49(11) . . ? C8 Fe1 C9 139.51(11) 2_665 . ? C5 Fe1 C9 40.95(10) 2_665 2_665 ? C5 Fe1 C9 139.05(10) . 2_665 ? C6 Fe1 C9 68.61(11) 2_665 2_665 ? C6 Fe1 C9 111.39(12) . 2_665 ? C8 Fe1 C9 139.51(11) . 2_665 ? C8 Fe1 C9 40.49(11) 2_665 2_665 ? C9 Fe1 C9 180.0(2) . 2_665 ? C5 Fe1 C7 111.42(10) 2_665 . ? C5 Fe1 C7 68.58(10) . . ? C6 Fe1 C7 139.59(11) 2_665 . ? C6 Fe1 C7 40.41(11) . . ? C8 Fe1 C7 40.47(13) . . ? C8 Fe1 C7 139.53(13) 2_665 . ? C9 Fe1 C7 68.21(12) . . ? C9 Fe1 C7 111.79(12) 2_665 . ? C5 Fe1 C7 68.58(10) 2_665 2_665 ? C5 Fe1 C7 111.42(10) . 2_665 ? C6 Fe1 C7 40.41(11) 2_665 2_665 ? C6 Fe1 C7 139.59(11) . 2_665 ? C8 Fe1 C7 139.53(13) . 2_665 ? C8 Fe1 C7 40.47(13) 2_665 2_665 ? C9 Fe1 C7 111.79(12) . 2_665 ? C9 Fe1 C7 68.21(12) 2_665 2_665 ? C7 Fe1 C7 180.00(9) . 2_665 ? O2 C4 O3 124.2(2) . . ? O2 C4 C5 117.5(2) . . ? O3 C4 C5 118.3(2) . . ? C9 C5 C6 107.3(2) . . ? C9 C5 C4 125.1(2) . . ? C6 C5 C4 127.3(2) . . ? C9 C5 Fe1 69.90(14) . . ? C6 C5 Fe1 69.55(14) . . ? C4 C5 Fe1 121.60(17) . . ? C8 C9 C5 107.9(2) . . ? C8 C9 Fe1 69.61(14) . . ? C5 C9 Fe1 69.15(13) . . ? C8 C9 H9 126.1 . . ? C5 C9 H9 126.1 . . ? Fe1 C9 H9 126.1 . . ? C7 C6 C5 108.2(3) . . ? C7 C6 Fe1 70.13(17) . . ? C5 C6 Fe1 69.38(14) . . ? C7 C6 H6 125.9 . . ? C5 C6 H6 125.9 . . ? Fe1 C6 H6 125.9 . . ? C7 C8 C9 108.4(2) . . ? C7 C8 Fe1 69.95(15) . . ? C9 C8 Fe1 69.89(14) . . ? C7 C8 H8 125.8 . . ? C9 C8 H8 125.8 . . ? Fe1 C8 H8 125.8 . . ? C6 C7 C8 108.2(2) . . ? C6 C7 Fe1 69.46(15) . . ? C8 C7 Fe1 69.58(17) . . ? C6 C7 H7 125.9 . . ? C8 C7 H7 125.9 . . ? Fe1 C7 H7 125.9 . . ? C11 N10 H10A 109.5 . . ? C11 N10 H10B 109.5 . . ? H10A N10 H10B 109.5 . . ? C11 N10 H10C 109.5 . . ? H10A N10 H10C 109.5 . . ? H10B N10 H10C 109.5 . . ? C20 C19 C18 114.8(3) . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19B 108.6 . . ? C18 C19 H19B 108.6 . . ? H19A C19 H19B 107.5 . . ? C20 C21 C22 114.1(3) . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21B 108.7 . . ? C22 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? N10 C11 C12 112.1(2) . . ? N10 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? N10 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 112.7(2) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 112.6(2) . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C16 C17 C18 114.8(3) . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17B 108.6 . . ? C18 C17 H17B 108.6 . . ? H17A C17 H17B 107.5 . . ? C14 C15 C16 113.4(3) . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C19 C18 C17 115.4(3) . . ? C19 C18 H18A 108.4 . . ? C17 C18 H18A 108.4 . . ? C19 C18 H18B 108.4 . . ? C17 C18 H18B 108.4 . . ? H18A C18 H18B 107.5 . . ? C17 C16 C15 115.1(3) . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? C15 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C13 C14 C15 115.8(3) . . ? C13 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? C13 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C19 C20 C21 114.9(3) . . ? C19 C20 H20A 108.5 . . ? C21 C20 H20A 108.5 . . ? C19 C20 H20B 108.5 . . ? C21 C20 H20B 108.5 . . ? H20A C20 H20B 107.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10A O3 0.89 1.91 2.775(3) 164.6 2_565 N10 H10B O3 0.89 1.87 2.724(3) 159.5 1_445 N10 H10C O2 0.89 1.82 2.697(3) 166.6 1_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.348 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.105 # Attachment '1(12)_ps0730r.cif' data_ps0730r _database_code_depnum_ccdc_archive 'CCDC 795751' #TrackingRef '1(12)_ps0730r.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration syn _chemical_melting_point ? _chemical_formula_moiety '2(C13 H21 N), C12 H8 Fe O4' _chemical_formula_sum 'C38 H68 Fe N2 O4' _chemical_formula_weight 672.79 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' Fe Fe 0.3463 0.8444 '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' H H 0.0000 0.0000 '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 6.383(3) _cell_length_b 9.819(4) _cell_length_c 16.098(7) _cell_angle_alpha 76.759(7) _cell_angle_beta 85.454(6) _cell_angle_gamma 88.787(6) _cell_volume 979.0(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description NIDDLE _exptl_crystal_colour BROWN _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.423 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8766 _exptl_absorpt_correction_T_max 0.9316 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9480 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3442 _reflns_number_gt 3180 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.1094P)^2^+0.2169P] 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 3442 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1658 _refine_ls_wR_factor_gt 0.1575 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 1.0000 0.5000 0.0000 0.0440(2) Uani 1 2 d S . . O2 O 0.5363(3) 0.7318(2) 0.04129(15) 0.0647(6) Uani 1 1 d . . . O3 O 0.8311(3) 0.83364(19) 0.05688(14) 0.0589(5) Uani 1 1 d . . . C4 C 0.7222(4) 0.7265(3) 0.05930(16) 0.0471(6) Uani 1 1 d . . . C5 C 0.8221(4) 0.5858(3) 0.08499(16) 0.0474(6) Uani 1 1 d . . . C6 C 0.7319(4) 0.4568(3) 0.07865(19) 0.0579(7) Uani 1 1 d . . . H6 H 0.5914 0.4448 0.0608 0.069 Uiso 1 1 calc R . . C7 C 0.8827(5) 0.3496(3) 0.1017(2) 0.0673(8) Uani 1 1 d . . . H7 H 0.8649 0.2505 0.1022 0.081 Uiso 1 1 calc R . . C8 C 1.0642(5) 0.4103(3) 0.12277(19) 0.0676(8) Uani 1 1 d . . . H8 H 1.1938 0.3607 0.1405 0.081 Uiso 1 1 calc R . . C9 C 1.0272(4) 0.5555(3) 0.11269(18) 0.0554(7) Uani 1 1 d . . . H9 H 1.1267 0.6238 0.1225 0.066 Uiso 1 1 calc R . . N10 N 0.2313(3) -0.0794(2) 0.06431(15) 0.0547(6) Uani 1 1 d . . . H10A H 0.2395 0.0017 0.0258 0.082 Uiso 1 1 calc R . . H10B H 0.1159 -0.1246 0.0584 0.082 Uiso 1 1 calc R . . H10C H 0.3439 -0.1313 0.0563 0.082 Uiso 1 1 calc R . . C11 C 0.2227(5) -0.0531(4) 0.1513(2) 0.0679(8) Uani 1 1 d . . . H11A H 0.1950 -0.1405 0.1929 0.082 Uiso 1 1 calc R . . H11B H 0.1071 0.0103 0.1579 0.082 Uiso 1 1 calc R . . C12 C 0.4217(5) 0.0084(4) 0.1695(2) 0.0656(8) Uani 1 1 d . . . H12A H 0.4455 0.0981 0.1297 0.079 Uiso 1 1 calc R . . H12B H 0.5383 -0.0527 0.1600 0.079 Uiso 1 1 calc R . . C13 C 0.4176(5) 0.0286(4) 0.2605(2) 0.0726(9) Uani 1 1 d . . . H13A H 0.3061 0.0940 0.2688 0.087 Uiso 1 1 calc R . . H13B H 0.3849 -0.0601 0.3001 0.087 Uiso 1 1 calc R . . C14 C 0.6221(6) 0.0825(4) 0.2814(2) 0.0736(9) Uani 1 1 d . . . H14A H 0.7333 0.0177 0.2718 0.088 Uiso 1 1 calc R . . H14B H 0.6531 0.1716 0.2419 0.088 Uiso 1 1 calc R . . C15 C 0.6262(5) 0.1021(4) 0.3712(2) 0.0723(8) Uani 1 1 d . . . H15A H 0.6007 0.0126 0.4110 0.087 Uiso 1 1 calc R . . H15B H 0.5130 0.1649 0.3818 0.087 Uiso 1 1 calc R . . C16 C 0.8319(5) 0.1605(4) 0.3885(2) 0.0756(9) Uani 1 1 d . . . H16A H 0.9434 0.0951 0.3803 0.091 Uiso 1 1 calc R . . H16B H 0.8606 0.2471 0.3462 0.091 Uiso 1 1 calc R . . C17 C 0.8403(6) 0.1890(4) 0.4759(2) 0.0773(9) Uani 1 1 d . . . H17A H 0.7267 0.2525 0.4849 0.093 Uiso 1 1 calc R . . H17B H 0.8162 0.1019 0.5183 0.093 Uiso 1 1 calc R . . C18 C 1.0434(6) 0.2507(4) 0.4907(2) 0.0815(10) Uani 1 1 d . . . H18A H 1.0665 0.3379 0.4484 0.098 Uiso 1 1 calc R . . H18B H 1.1568 0.1875 0.4810 0.098 Uiso 1 1 calc R . . C19 C 1.0569(6) 0.2792(5) 0.5784(3) 0.0856(10) Uani 1 1 d . . . H19A H 0.9437 0.3422 0.5886 0.103 Uiso 1 1 calc R . . H19B H 1.0360 0.1920 0.6209 0.103 Uiso 1 1 calc R . . C20 C 1.2626(7) 0.3423(5) 0.5904(3) 0.1044(14) Uani 1 1 d . . . C21A C 1.2744(15) 0.3359(11) 0.6967(6) 0.091(2) Uiso 0.49 1 d P . . C21B C 1.2815(15) 0.3960(11) 0.6630(6) 0.095(2) Uiso 0.51 1 d P . . C22A C 1.5067(15) 0.3767(10) 0.7204(6) 0.101(2) Uiso 0.52 1 d P . . C22B C 1.524(2) 0.4618(14) 0.6524(8) 0.120(3) Uiso 0.48 1 d P . . C23A C 1.504(4) 0.526(2) 0.6829(16) 0.167(8) Uiso 0.40 1 d P . . C23B C 1.5768(19) 0.5038(12) 0.7268(8) 0.141(4) Uiso 0.60 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0409(3) 0.0359(3) 0.0515(3) -0.0060(2) 0.0065(2) 0.00306(19) O2 0.0383(10) 0.0648(12) 0.0987(16) -0.0323(11) -0.0147(10) 0.0114(8) O3 0.0420(10) 0.0483(10) 0.0901(14) -0.0218(10) -0.0121(9) 0.0064(8) C4 0.0370(12) 0.0529(14) 0.0544(14) -0.0198(11) -0.0013(10) 0.0073(10) C5 0.0422(13) 0.0482(14) 0.0509(14) -0.0129(11) 0.0046(10) 0.0055(10) C6 0.0489(15) 0.0534(15) 0.0669(17) -0.0112(13) 0.0173(12) -0.0075(12) C7 0.077(2) 0.0442(15) 0.0691(18) -0.0003(13) 0.0229(16) 0.0030(14) C8 0.073(2) 0.0621(18) 0.0589(17) -0.0005(14) 0.0005(14) 0.0260(15) C9 0.0519(15) 0.0590(16) 0.0562(15) -0.0144(12) -0.0084(12) 0.0125(12) N10 0.0378(11) 0.0560(13) 0.0732(15) -0.0195(11) -0.0105(10) 0.0076(9) C11 0.0507(16) 0.081(2) 0.075(2) -0.0253(16) 0.0001(14) 0.0040(14) C12 0.0563(17) 0.076(2) 0.0667(18) -0.0213(15) 0.0001(14) 0.0009(14) C13 0.069(2) 0.087(2) 0.0656(19) -0.0268(17) 0.0038(15) -0.0030(17) C14 0.073(2) 0.087(2) 0.0627(18) -0.0242(16) 0.0055(15) -0.0079(17) C15 0.073(2) 0.082(2) 0.0624(18) -0.0213(16) 0.0027(15) -0.0053(17) C16 0.072(2) 0.088(2) 0.069(2) -0.0243(17) 0.0040(16) -0.0085(17) C17 0.072(2) 0.090(2) 0.073(2) -0.0272(18) 0.0027(16) -0.0027(18) C18 0.073(2) 0.092(3) 0.084(2) -0.030(2) 0.0021(18) -0.0067(18) C19 0.076(2) 0.100(3) 0.089(2) -0.041(2) -0.0005(19) -0.005(2) C20 0.079(3) 0.127(4) 0.124(4) -0.062(3) -0.005(2) -0.014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C5 2.028(2) 2_765 ? Fe1 C5 2.028(2) . ? Fe1 C9 2.031(3) 2_765 ? Fe1 C9 2.031(3) . ? Fe1 C6 2.038(3) . ? Fe1 C6 2.038(3) 2_765 ? Fe1 C8 2.041(3) . ? Fe1 C8 2.041(3) 2_765 ? Fe1 C7 2.041(3) . ? Fe1 C7 2.041(3) 2_765 ? O2 C4 1.241(3) . ? O3 C4 1.265(3) . ? C4 C5 1.493(3) . ? C5 C9 1.420(4) . ? C5 C6 1.431(4) . ? C6 C7 1.417(4) . ? C6 H6 0.9800 . ? C7 C8 1.413(5) . ? C7 H7 0.9800 . ? C8 C9 1.415(4) . ? C8 H8 0.9800 . ? C9 H9 0.9800 . ? N10 C11 1.478(4) . ? N10 H10A 0.8900 . ? N10 H10B 0.8900 . ? N10 H10C 0.8900 . ? C11 C12 1.495(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.521(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.509(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.503(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.514(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.502(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.502(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.509(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.508(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21B 1.402(10) . ? C20 C21A 1.705(10) . ? C21A C21B 0.704(11) . ? C21A C22A 1.641(13) . ? C21A C22B 2.019(16) . ? C21B C22B 1.672(15) . ? C21B C22A 1.754(13) . ? C22A C22B 1.214(15) . ? C22A C23B 1.362(14) . ? C22A C23A 1.45(2) . ? C22B C23A 0.89(2) . ? C22B C23B 1.418(18) . ? C23A C23B 0.86(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Fe1 C5 180.000(1) 2_765 . ? C5 Fe1 C9 40.96(11) 2_765 2_765 ? C5 Fe1 C9 139.04(11) . 2_765 ? C5 Fe1 C9 139.04(11) 2_765 . ? C5 Fe1 C9 40.96(11) . . ? C9 Fe1 C9 180.00(14) 2_765 . ? C5 Fe1 C6 138.80(11) 2_765 . ? C5 Fe1 C6 41.20(11) . . ? C9 Fe1 C6 111.24(12) 2_765 . ? C9 Fe1 C6 68.76(12) . . ? C5 Fe1 C6 41.20(11) 2_765 2_765 ? C5 Fe1 C6 138.80(11) . 2_765 ? C9 Fe1 C6 68.76(12) 2_765 2_765 ? C9 Fe1 C6 111.24(12) . 2_765 ? C6 Fe1 C6 180.0 . 2_765 ? C5 Fe1 C8 111.20(11) 2_765 . ? C5 Fe1 C8 68.80(11) . . ? C9 Fe1 C8 139.34(12) 2_765 . ? C9 Fe1 C8 40.66(12) . . ? C6 Fe1 C8 68.44(13) . . ? C6 Fe1 C8 111.56(13) 2_765 . ? C5 Fe1 C8 68.80(11) 2_765 2_765 ? C5 Fe1 C8 111.20(11) . 2_765 ? C9 Fe1 C8 40.66(12) 2_765 2_765 ? C9 Fe1 C8 139.34(12) . 2_765 ? C6 Fe1 C8 111.56(13) . 2_765 ? C6 Fe1 C8 68.44(13) 2_765 2_765 ? C8 Fe1 C8 180.00(8) . 2_765 ? C5 Fe1 C7 111.13(11) 2_765 . ? C5 Fe1 C7 68.87(11) . . ? C9 Fe1 C7 111.59(13) 2_765 . ? C9 Fe1 C7 68.41(13) . . ? C6 Fe1 C7 40.64(12) . . ? C6 Fe1 C7 139.36(12) 2_765 . ? C8 Fe1 C7 40.51(14) . . ? C8 Fe1 C7 139.49(14) 2_765 . ? C5 Fe1 C7 68.87(11) 2_765 2_765 ? C5 Fe1 C7 111.13(11) . 2_765 ? C9 Fe1 C7 68.41(13) 2_765 2_765 ? C9 Fe1 C7 111.59(13) . 2_765 ? C6 Fe1 C7 139.36(12) . 2_765 ? C6 Fe1 C7 40.64(12) 2_765 2_765 ? C8 Fe1 C7 139.49(14) . 2_765 ? C8 Fe1 C7 40.51(14) 2_765 2_765 ? C7 Fe1 C7 180.0(2) . 2_765 ? O2 C4 O3 123.5(2) . . ? O2 C4 C5 118.0(2) . . ? O3 C4 C5 118.5(2) . . ? C9 C5 C6 107.4(2) . . ? C9 C5 C4 127.3(2) . . ? C6 C5 C4 125.1(2) . . ? C9 C5 Fe1 69.64(15) . . ? C6 C5 Fe1 69.78(14) . . ? C4 C5 Fe1 121.87(18) . . ? C7 C6 C5 107.8(3) . . ? C7 C6 Fe1 69.78(15) . . ? C5 C6 Fe1 69.02(14) . . ? C7 C6 H6 126.1 . . ? C5 C6 H6 126.1 . . ? Fe1 C6 H6 126.1 . . ? C8 C7 C6 108.3(3) . . ? C8 C7 Fe1 69.75(17) . . ? C6 C7 Fe1 69.58(16) . . ? C8 C7 H7 125.8 . . ? C6 C7 H7 125.8 . . ? Fe1 C7 H7 125.8 . . ? C7 C8 C9 108.1(3) . . ? C7 C8 Fe1 69.74(18) . . ? C9 C8 Fe1 69.30(16) . . ? C7 C8 H8 126.0 . . ? C9 C8 H8 126.0 . . ? Fe1 C8 H8 126.0 . . ? C8 C9 C5 108.4(3) . . ? C8 C9 Fe1 70.04(17) . . ? C5 C9 Fe1 69.40(15) . . ? C8 C9 H9 125.8 . . ? C5 C9 H9 125.8 . . ? Fe1 C9 H9 125.8 . . ? C11 N10 H10A 109.5 . . ? C11 N10 H10B 109.5 . . ? H10A N10 H10B 109.5 . . ? C11 N10 H10C 109.5 . . ? H10A N10 H10C 109.5 . . ? H10B N10 H10C 109.5 . . ? N10 C11 C12 112.7(2) . . ? N10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? N10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 112.8(3) . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 113.4(3) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C13 115.3(3) . . ? C15 C14 H14A 108.5 . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14B 108.5 . . ? C13 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C14 C15 C16 113.4(3) . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 115.6(3) . . ? C17 C16 H16A 108.4 . . ? C15 C16 H16A 108.4 . . ? C17 C16 H16B 108.4 . . ? C15 C16 H16B 108.4 . . ? H16A C16 H16B 107.5 . . ? C18 C17 C16 114.6(3) . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C16 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 115.7(3) . . ? C17 C18 H18A 108.3 . . ? C19 C18 H18A 108.3 . . ? C17 C18 H18B 108.3 . . ? C19 C18 H18B 108.3 . . ? H18A C18 H18B 107.4 . . ? C20 C19 C18 114.1(3) . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19B 108.7 . . ? C18 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C21B C20 C19 119.5(5) . . ? C21B C20 C21A 23.7(5) . . ? C19 C20 C21A 108.4(5) . . ? C21B C21A C22A 87.3(13) . . ? C21B C21A C20 53.2(11) . . ? C22A C21A C20 113.0(7) . . ? C21B C21A C22B 51.3(12) . . ? C22A C21A C22B 36.9(5) . . ? C20 C21A C22B 82.2(6) . . ? C21A C21B C20 103.1(14) . . ? C21A C21B C22B 109.5(14) . . ? C20 C21B C22B 105.9(8) . . ? C21A C21B C22A 69.1(12) . . ? C20 C21B C22A 123.9(7) . . ? C22B C21B C22A 41.4(5) . . ? C22B C22A C23B 66.5(10) . . ? C22B C22A C23A 37.5(10) . . ? C23B C22A C23A 35.4(9) . . ? C22B C22A C21A 88.7(9) . . ? C23B C22A C21A 128.5(10) . . ? C23A C22A C21A 99.1(12) . . ? C22B C22A C21B 65.7(8) . . ? C23B C22A C21B 110.7(9) . . ? C23A C22A C21B 77.5(11) . . ? C21A C22A C21B 23.6(4) . . ? C23A C22B C22A 86(2) . . ? C23A C22B C23B 35.2(18) . . ? C22A C22B C23B 61.8(9) . . ? C23A C22B C21B 100(2) . . ? C22A C22B C21B 72.9(9) . . ? C23B C22B C21B 112.5(10) . . ? C23A C22B C21A 101(2) . . ? C22A C22B C21A 54.3(7) . . ? C23B C22B C21A 102.5(9) . . ? C21B C22B C21A 19.2(4) . . ? C23B C23A C22B 108(3) . . ? C23B C23A C22A 66.4(19) . . ? C22B C23A C22A 56.4(17) . . ? C23A C23B C22A 78(2) . . ? C23A C23B C22B 36.4(18) . . ? C22A C23B C22B 51.7(7) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10A O3 0.89 1.91 2.778(3) 162.8 2_665 N10 H10B O3 0.89 1.88 2.731(3) 160.5 1_445 N10 H10C O2 0.89 1.85 2.722(3) 167.9 1_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.780 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.116 # Attachment '1(13)_ps0733m.cif' data_ps0733m _database_code_depnum_ccdc_archive 'CCDC 795752' #TrackingRef '1(13)_ps0733m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration syn _chemical_melting_point ? _chemical_formula_moiety '2(C14 H32 N), C12 H8 Fe O4' _chemical_formula_sum 'C40 H72 Fe N2 O4' _chemical_formula_weight 700.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.0000 0.0000 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' _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 6.3805(8) _cell_length_b 9.7435(13) _cell_length_c 17.269(2) _cell_angle_alpha 103.524(2) _cell_angle_beta 97.318(2) _cell_angle_gamma 91.618(2) _cell_volume 1033.4(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description NIDDLE _exptl_crystal_colour BROWN _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.126 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.403 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8819 _exptl_absorpt_correction_T_max 0.9383 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10078 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3642 _reflns_number_gt 3372 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0750P)^2^+0.1971P] 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 SHELXL _refine_ls_extinction_coef 0.002(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3642 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.0000 0.0000 0.0000 0.0407(2) Uani 1 2 d S . . O2 O 0.1854(3) 0.37715(17) 0.05567(11) 0.0535(4) Uani 1 1 d . . . O3 O 0.4787(3) 0.26163(19) 0.04482(13) 0.0641(5) Uani 1 1 d . . . C4 C 0.2933(4) 0.2712(2) 0.05956(14) 0.0445(5) Uani 1 1 d . . . C5 C 0.1917(4) 0.1494(2) 0.08212(14) 0.0434(5) Uani 1 1 d . . . C6 C 0.2766(4) 0.0146(3) 0.07610(16) 0.0546(7) Uani 1 1 d . . . H6 H 0.4151 -0.0115 0.0604 0.065 Uiso 1 1 calc R . . C7 C 0.1244(5) -0.0761(3) 0.09490(17) 0.0654(8) Uani 1 1 d . . . H7 H 0.1392 -0.1761 0.0946 0.078 Uiso 1 1 calc R . . C8 C -0.0535(5) 0.0022(3) 0.11429(16) 0.0646(8) Uani 1 1 d . . . H8 H -0.1829 -0.0343 0.1295 0.078 Uiso 1 1 calc R . . C9 C -0.0136(4) 0.1412(3) 0.10662(15) 0.0520(6) Uani 1 1 d . . . H9 H -0.1098 0.2182 0.1158 0.062 Uiso 1 1 calc R . . N10 N 0.7841(3) -0.5338(2) 0.05822(13) 0.0510(5) Uani 1 1 d . . . H10A H 0.6722 -0.5939 0.0520 0.076 Uiso 1 1 calc R . . H10B H 0.8997 -0.5819 0.0519 0.076 Uiso 1 1 calc R . . H10C H 0.7653 -0.4825 0.0217 0.076 Uiso 1 1 calc R . . C11 C 0.8092(4) -0.4387(3) 0.14005(18) 0.0620(7) Uani 1 1 d . . . H11A H 0.9321 -0.3740 0.1468 0.074 Uiso 1 1 calc R . . H11B H 0.8339 -0.4948 0.1796 0.074 Uiso 1 1 calc R . . C12 C 0.6186(4) -0.3556(3) 0.15491(16) 0.0595(7) Uani 1 1 d . . . H12A H 0.4952 -0.4205 0.1467 0.071 Uiso 1 1 calc R . . H12B H 0.5962 -0.2979 0.1161 0.071 Uiso 1 1 calc R . . C13 C 0.6397(5) -0.2604(3) 0.23942(17) 0.0637(7) Uani 1 1 d . . . H13A H 0.6670 -0.3174 0.2783 0.076 Uiso 1 1 calc R . . H13B H 0.7597 -0.1929 0.2470 0.076 Uiso 1 1 calc R . . C14 C 0.4446(5) -0.1818(3) 0.25445(17) 0.0694(8) Uani 1 1 d . . . H14A H 0.3253 -0.2503 0.2451 0.083 Uiso 1 1 calc R . . H14B H 0.4192 -0.1251 0.2152 0.083 Uiso 1 1 calc R . . C15 C 0.4499(5) -0.0859(3) 0.33746(16) 0.0655(8) Uani 1 1 d . . . H15A H 0.4758 -0.1417 0.3771 0.079 Uiso 1 1 calc R . . H15B H 0.5670 -0.0157 0.3468 0.079 Uiso 1 1 calc R . . C16 C 0.2481(5) -0.0107(3) 0.34960(17) 0.0691(8) Uani 1 1 d . . . H16A H 0.2196 0.0417 0.3085 0.083 Uiso 1 1 calc R . . H16B H 0.1321 -0.0813 0.3419 0.083 Uiso 1 1 calc R . . C17 C 0.2515(5) 0.0899(3) 0.43091(18) 0.0691(8) Uani 1 1 d . . . H17A H 0.3665 0.1610 0.4385 0.083 Uiso 1 1 calc R . . H17B H 0.2808 0.0377 0.4721 0.083 Uiso 1 1 calc R . . C18 C 0.0480(5) 0.1637(3) 0.44258(18) 0.0702(8) Uani 1 1 d . . . H18A H 0.0184 0.2155 0.4012 0.084 Uiso 1 1 calc R . . H18B H -0.0670 0.0926 0.4352 0.084 Uiso 1 1 calc R . . C19 C 0.0515(5) 0.2649(3) 0.52383(18) 0.0710(8) Uani 1 1 d . . . H19A H 0.1666 0.3359 0.5312 0.085 Uiso 1 1 calc R . . H19B H 0.0811 0.2130 0.5652 0.085 Uiso 1 1 calc R . . C20 C -0.1515(5) 0.3391(3) 0.53580(18) 0.0710(8) Uani 1 1 d . . . H20A H -0.2668 0.2681 0.5282 0.085 Uiso 1 1 calc R . . H20B H -0.1807 0.3914 0.4947 0.085 Uiso 1 1 calc R . . C21 C -0.1481(5) 0.4401(3) 0.61752(19) 0.0729(8) Uani 1 1 d . . . H21A H -0.1196 0.3875 0.6586 0.087 Uiso 1 1 calc R . . H21B H -0.0321 0.5106 0.6252 0.087 Uiso 1 1 calc R . . C22 C -0.3495(5) 0.5151(3) 0.62970(19) 0.0724(8) Uani 1 1 d . . . H22A H -0.4653 0.4445 0.6223 0.087 Uiso 1 1 calc R . . H22B H -0.3785 0.5670 0.5883 0.087 Uiso 1 1 calc R . . C23 C -0.3465(6) 0.6166(4) 0.7108(2) 0.0802(9) Uani 1 1 d . . . H23A H -0.3190 0.5649 0.7523 0.096 Uiso 1 1 calc R . . H23B H -0.2306 0.6872 0.7185 0.096 Uiso 1 1 calc R . . C24 C -0.5493(6) 0.6911(4) 0.7213(2) 0.0965(12) Uani 1 1 d . . . H24A H -0.5734 0.7475 0.6827 0.145 Uiso 1 1 calc R . . H24B H -0.5378 0.7508 0.7746 0.145 Uiso 1 1 calc R . . H24C H -0.6654 0.6221 0.7133 0.145 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0358(3) 0.0371(3) 0.0494(3) 0.0192(2) -0.00807(19) -0.00790(19) O2 0.0407(9) 0.0421(9) 0.0813(12) 0.0179(9) 0.0158(8) 0.0014(7) O3 0.0364(10) 0.0501(10) 0.1084(16) 0.0176(10) 0.0231(10) -0.0024(8) C4 0.0379(13) 0.0426(13) 0.0487(13) 0.0043(10) 0.0038(10) -0.0050(10) C5 0.0365(12) 0.0434(13) 0.0478(13) 0.0112(10) -0.0017(10) -0.0072(10) C6 0.0432(14) 0.0511(15) 0.0647(16) 0.0180(12) -0.0167(12) -0.0021(11) C7 0.073(2) 0.0533(16) 0.0687(18) 0.0333(14) -0.0248(15) -0.0162(14) C8 0.0633(18) 0.0772(19) 0.0569(16) 0.0314(14) -0.0007(13) -0.0263(15) C9 0.0491(15) 0.0525(14) 0.0546(15) 0.0129(12) 0.0099(11) -0.0074(11) N10 0.0392(11) 0.0485(12) 0.0678(14) 0.0151(10) 0.0158(10) -0.0011(9) C11 0.0505(16) 0.0626(17) 0.0699(18) 0.0118(14) 0.0062(13) -0.0045(13) C12 0.0518(16) 0.0647(17) 0.0583(16) 0.0098(13) 0.0034(12) -0.0004(13) C13 0.0625(18) 0.0652(18) 0.0572(16) 0.0062(13) 0.0012(13) 0.0029(14) C14 0.072(2) 0.076(2) 0.0521(16) 0.0043(14) -0.0040(14) 0.0083(16) C15 0.0702(19) 0.0660(18) 0.0525(16) 0.0051(13) -0.0038(13) 0.0043(15) C16 0.0698(19) 0.0707(19) 0.0581(17) 0.0052(14) -0.0044(14) 0.0058(15) C17 0.0671(19) 0.0688(19) 0.0632(18) 0.0055(14) -0.0028(14) 0.0033(15) C18 0.0661(19) 0.0715(19) 0.0659(18) 0.0069(15) 0.0001(15) 0.0033(15) C19 0.0674(19) 0.0700(19) 0.0683(19) 0.0065(15) 0.0008(15) 0.0021(15) C20 0.068(2) 0.0712(19) 0.0674(19) 0.0069(15) 0.0047(15) 0.0019(15) C21 0.071(2) 0.073(2) 0.0677(19) 0.0068(15) 0.0028(15) 0.0025(16) C22 0.070(2) 0.076(2) 0.0651(18) 0.0077(15) 0.0071(15) -0.0017(16) C23 0.083(2) 0.083(2) 0.0679(19) 0.0047(17) 0.0075(17) 0.0054(18) C24 0.093(3) 0.103(3) 0.086(2) 0.005(2) 0.019(2) 0.013(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C5 2.029(2) 2 ? Fe1 C5 2.029(2) . ? Fe1 C7 2.034(2) . ? Fe1 C7 2.034(2) 2 ? Fe1 C9 2.038(3) 2 ? Fe1 C9 2.038(3) . ? Fe1 C8 2.041(3) . ? Fe1 C8 2.041(3) 2 ? Fe1 C6 2.042(2) 2 ? Fe1 C6 2.042(2) . ? O2 C4 1.267(3) . ? O3 C4 1.243(3) . ? C4 C5 1.489(3) . ? C5 C6 1.422(3) . ? C5 C9 1.432(3) . ? C6 C7 1.413(4) . ? C6 H6 0.9800 . ? C7 C8 1.417(4) . ? C7 H7 0.9800 . ? C8 C9 1.410(4) . ? C8 H8 0.9800 . ? C9 H9 0.9800 . ? N10 C11 1.484(3) . ? N10 H10A 0.8900 . ? N10 H10B 0.8900 . ? N10 H10C 0.8900 . ? C11 C12 1.497(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.523(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.499(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.513(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.512(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.510(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.515(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.512(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.515(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.517(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.510(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.512(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.511(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Fe1 C5 180.00(18) 2 . ? C5 Fe1 C7 111.27(10) 2 . ? C5 Fe1 C7 68.73(10) . . ? C5 Fe1 C7 68.73(10) 2 2 ? C5 Fe1 C7 111.27(10) . 2 ? C7 Fe1 C7 180.00(13) . 2 ? C5 Fe1 C9 41.24(10) 2 2 ? C5 Fe1 C9 138.76(10) . 2 ? C7 Fe1 C9 111.50(12) . 2 ? C7 Fe1 C9 68.50(12) 2 2 ? C5 Fe1 C9 138.76(10) 2 . ? C5 Fe1 C9 41.24(10) . . ? C7 Fe1 C9 68.50(12) . . ? C7 Fe1 C9 111.50(12) 2 . ? C9 Fe1 C9 180.0(2) 2 . ? C5 Fe1 C8 111.26(10) 2 . ? C5 Fe1 C8 68.74(10) . . ? C7 Fe1 C8 40.72(13) . . ? C7 Fe1 C8 139.28(13) 2 . ? C9 Fe1 C8 139.54(11) 2 . ? C9 Fe1 C8 40.46(11) . . ? C5 Fe1 C8 68.74(10) 2 2 ? C5 Fe1 C8 111.26(10) . 2 ? C7 Fe1 C8 139.28(13) . 2 ? C7 Fe1 C8 40.72(13) 2 2 ? C9 Fe1 C8 40.46(11) 2 2 ? C9 Fe1 C8 139.54(11) . 2 ? C8 Fe1 C8 180.0 . 2 ? C5 Fe1 C6 40.88(10) 2 2 ? C5 Fe1 C6 139.12(10) . 2 ? C7 Fe1 C6 139.44(11) . 2 ? C7 Fe1 C6 40.56(11) 2 2 ? C9 Fe1 C6 68.73(11) 2 2 ? C9 Fe1 C6 111.27(11) . 2 ? C8 Fe1 C6 111.63(12) . 2 ? C8 Fe1 C6 68.37(12) 2 2 ? C5 Fe1 C6 139.12(10) 2 . ? C5 Fe1 C6 40.88(10) . . ? C7 Fe1 C6 40.56(11) . . ? C7 Fe1 C6 139.44(11) 2 . ? C9 Fe1 C6 111.27(11) 2 . ? C9 Fe1 C6 68.73(11) . . ? C8 Fe1 C6 68.37(12) . . ? C8 Fe1 C6 111.63(12) 2 . ? C6 Fe1 C6 180.00(16) 2 . ? O3 C4 O2 124.1(2) . . ? O3 C4 C5 117.7(2) . . ? O2 C4 C5 118.2(2) . . ? C6 C5 C9 107.6(2) . . ? C6 C5 C4 125.1(2) . . ? C9 C5 C4 127.1(2) . . ? C6 C5 Fe1 70.04(13) . . ? C9 C5 Fe1 69.71(13) . . ? C4 C5 Fe1 121.59(16) . . ? C7 C6 C5 108.0(2) . . ? C7 C6 Fe1 69.40(14) . . ? C5 C6 Fe1 69.07(13) . . ? C7 C6 H6 126.0 . . ? C5 C6 H6 126.0 . . ? Fe1 C6 H6 126.0 . . ? C6 C7 C8 108.3(2) . . ? C6 C7 Fe1 70.04(14) . . ? C8 C7 Fe1 69.91(15) . . ? C6 C7 H7 125.9 . . ? C8 C7 H7 125.9 . . ? Fe1 C7 H7 125.9 . . ? C9 C8 C7 108.3(2) . . ? C9 C8 Fe1 69.67(14) . . ? C7 C8 Fe1 69.38(16) . . ? C9 C8 H8 125.9 . . ? C7 C8 H8 125.9 . . ? Fe1 C8 H8 125.9 . . ? C8 C9 C5 107.8(2) . . ? C8 C9 Fe1 69.87(16) . . ? C5 C9 Fe1 69.05(13) . . ? C8 C9 H9 126.1 . . ? C5 C9 H9 126.1 . . ? Fe1 C9 H9 126.1 . . ? C11 N10 H10A 109.5 . . ? C11 N10 H10B 109.5 . . ? H10A N10 H10B 109.5 . . ? C11 N10 H10C 109.5 . . ? H10A N10 H10C 109.5 . . ? H10B N10 H10C 109.5 . . ? N10 C11 C12 112.1(2) . . ? N10 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? N10 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 112.7(2) . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 112.2(2) . . ? C14 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? C14 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C13 C14 C15 115.9(2) . . ? C13 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? C13 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C16 C15 C14 113.6(2) . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? C14 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 114.9(2) . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? C15 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C16 C17 C18 114.4(2) . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C19 C18 C17 114.5(2) . . ? C19 C18 H18A 108.6 . . ? C17 C18 H18A 108.6 . . ? C19 C18 H18B 108.6 . . ? C17 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C18 C19 C20 114.7(2) . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19B 108.6 . . ? C20 C19 H19B 108.6 . . ? H19A C19 H19B 107.6 . . ? C19 C20 C21 114.6(3) . . ? C19 C20 H20A 108.6 . . ? C21 C20 H20A 108.6 . . ? C19 C20 H20B 108.6 . . ? C21 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? C22 C21 C20 114.9(3) . . ? C22 C21 H21A 108.5 . . ? C20 C21 H21A 108.5 . . ? C22 C21 H21B 108.5 . . ? C20 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C21 C22 C23 115.1(3) . . ? C21 C22 H22A 108.5 . . ? C23 C22 H22A 108.5 . . ? C21 C22 H22B 108.5 . . ? C23 C22 H22B 108.5 . . ? H22A C22 H22B 107.5 . . ? C24 C23 C22 114.1(3) . . ? C24 C23 H23A 108.7 . . ? C22 C23 H23A 108.7 . . ? C24 C23 H23B 108.7 . . ? C22 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? 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 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10C O2 0.89 1.92 2.779(3) 162.8 2_655 N10 H10B O2 0.89 1.87 2.729(3) 160.7 1_645 N10 H10A O3 0.89 1.82 2.697(3) 169.5 1_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.392 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.095 # Attachment '1(14)_pso736m.cif' data_pso736m _database_code_depnum_ccdc_archive 'CCDC 795753' #TrackingRef '1(14)_pso736m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C15 H27 N), C12 H8 Fe O4' _chemical_formula_sum 'C42 H76 Fe N2 O4' _chemical_formula_weight 728.90 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' Fe Fe 0.3463 0.8444 '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' _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 6.418(2) _cell_length_b 9.720(3) _cell_length_c 18.006(6) _cell_angle_alpha 104.624(5) _cell_angle_beta 98.504(6) _cell_angle_gamma 91.086(5) _cell_volume 1073.1(6) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description NIDDLE _exptl_crystal_colour BROWN _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.128 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.390 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8852 _exptl_absorpt_correction_T_max 0.9402 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II' _diffrn_measurement_method 'Phi-Omega scan' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10282 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3779 _reflns_number_gt 3693 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 2.3' _computing_publication_material Shelxl-97 _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^)+(0.0991P)^2^+0.4369P] 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 SHELXL _refine_ls_extinction_coef 0.024(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3779 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1627 _refine_ls_wR_factor_gt 0.1576 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 0.5000 0.5000 0.0415(2) Uani 1 2 d S . . O2 O 0.0283(3) 0.2348(2) 0.46193(13) 0.0626(5) Uani 1 1 d . . . O3 O 0.3187(3) 0.11921(19) 0.44725(12) 0.0571(5) Uani 1 1 d . . . C4 C 0.2095(4) 0.2256(2) 0.44542(14) 0.0450(5) Uani 1 1 d . . . C5 C 0.3034(4) 0.3469(3) 0.42260(14) 0.0452(5) Uani 1 1 d . . . C6 C 0.5013(4) 0.3547(3) 0.39685(15) 0.0535(6) Uani 1 1 d . . . H6 H 0.5975 0.2773 0.3870 0.064 Uiso 1 1 calc R . . C7 C 0.5365(5) 0.4942(3) 0.38864(16) 0.0645(8) Uani 1 1 d . . . H7 H 0.6614 0.5301 0.3724 0.077 Uiso 1 1 calc R . . C8 C 0.3618(5) 0.5728(3) 0.40906(17) 0.0631(8) Uani 1 1 d . . . H8 H 0.3449 0.6730 0.4095 0.076 Uiso 1 1 calc R . . C9 C 0.2159(4) 0.4831(3) 0.42959(16) 0.0550(6) Uani 1 1 d . . . H9 H 0.0805 0.5099 0.4463 0.066 Uiso 1 1 calc R . . N10 N 1.2823(3) -0.0272(2) 0.55911(13) 0.0514(5) Uani 1 1 d . . . H10A H 1.2641 0.0236 0.5241 0.077 Uiso 1 1 calc R . . H10B H 1.1704 -0.0873 0.5520 0.077 Uiso 1 1 calc R . . H10C H 1.3973 -0.0762 0.5537 0.077 Uiso 1 1 calc R . . C11 C 1.3075(5) 0.0699(3) 0.63844(18) 0.0632(7) Uani 1 1 d . . . H11A H 1.4232 0.1396 0.6446 0.076 Uiso 1 1 calc R . . H11B H 1.3435 0.0153 0.6763 0.076 Uiso 1 1 calc R . . C12 C 1.1119(5) 0.1459(3) 0.65429(17) 0.0615(7) Uani 1 1 d . . . H12A H 0.9948 0.0762 0.6457 0.074 Uiso 1 1 calc R . . H12B H 1.0797 0.2040 0.6179 0.074 Uiso 1 1 calc R . . C13 C 1.1335(5) 0.2406(4) 0.73712(18) 0.0672(8) Uani 1 1 d . . . H13A H 1.1737 0.1835 0.7734 0.081 Uiso 1 1 calc R . . H13B H 1.2455 0.3136 0.7447 0.081 Uiso 1 1 calc R . . C14 C 0.9333(5) 0.3112(4) 0.75500(18) 0.0689(8) Uani 1 1 d . . . H14A H 0.8216 0.2377 0.7465 0.083 Uiso 1 1 calc R . . H14B H 0.8941 0.3681 0.7185 0.083 Uiso 1 1 calc R . . C15 C 0.9460(5) 0.4058(3) 0.83687(17) 0.0663(8) Uani 1 1 d . . . H15A H 0.9788 0.3485 0.8736 0.080 Uiso 1 1 calc R . . H15B H 1.0608 0.4775 0.8463 0.080 Uiso 1 1 calc R . . C16 C 0.7443(5) 0.4796(4) 0.85167(18) 0.0699(8) Uani 1 1 d . . . H16A H 0.7081 0.5325 0.8130 0.084 Uiso 1 1 calc R . . H16B H 0.6314 0.4074 0.8444 0.084 Uiso 1 1 calc R . . C17 C 0.7542(5) 0.5802(4) 0.93131(18) 0.0692(8) Uani 1 1 d . . . H17A H 0.7855 0.5270 0.9701 0.083 Uiso 1 1 calc R . . H17B H 0.8694 0.6511 0.9393 0.083 Uiso 1 1 calc R . . C18 C 0.5539(5) 0.6556(4) 0.94380(19) 0.0713(8) Uani 1 1 d . . . H18A H 0.4392 0.5844 0.9357 0.086 Uiso 1 1 calc R . . H18B H 0.5225 0.7080 0.9046 0.086 Uiso 1 1 calc R . . C19 C 0.5596(5) 0.7579(4) 1.0232(2) 0.0720(8) Uani 1 1 d . . . H19A H 0.5905 0.7057 1.0624 0.086 Uiso 1 1 calc R . . H19B H 0.6741 0.8294 1.0313 0.086 Uiso 1 1 calc R . . C20 C 0.3587(5) 0.8320(4) 1.0344(2) 0.0745(9) Uani 1 1 d . . . H20A H 0.2442 0.7601 1.0251 0.089 Uiso 1 1 calc R . . H20B H 0.3294 0.8850 0.9955 0.089 Uiso 1 1 calc R . . C21 C 0.3584(6) 0.9333(4) 1.1139(2) 0.0770(9) Uani 1 1 d . . . H21A H 0.3870 0.8806 1.1531 0.092 Uiso 1 1 calc R . . H21B H 0.4722 1.0057 1.1234 0.092 Uiso 1 1 calc R . . C22 C 0.1554(6) 1.0055(4) 1.1232(3) 0.0932(12) Uani 1 1 d . . . H22A H 0.1262 1.0565 1.0833 0.112 Uiso 1 1 calc R . . H22B H 0.0423 0.9327 1.1141 0.112 Uiso 1 1 calc R . . C23 C 0.1505(9) 1.1077(6) 1.2006(4) 0.131(2) Uani 1 1 d . . . C24A C -0.0885(13) 1.1740(9) 1.1855(5) 0.094(2) Uiso 0.60 1 d P . . C24B C -0.066(2) 1.1438(14) 1.2436(8) 0.108(3) Uiso 0.40 1 d P . . C25A C -0.1224(13) 1.2817(8) 1.2536(5) 0.125(2) Uiso 0.79 1 d P . . C25B C -0.051(5) 1.259(4) 1.2019(19) 0.124(8) Uiso 0.21 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0394(3) 0.0389(3) 0.0465(3) 0.0162(2) -0.00062(19) -0.00432(19) O2 0.0421(10) 0.0526(10) 0.0940(15) 0.0142(10) 0.0223(9) -0.0027(8) O3 0.0443(10) 0.0463(10) 0.0845(13) 0.0196(9) 0.0180(9) 0.0000(8) C4 0.0377(12) 0.0421(12) 0.0516(13) 0.0062(10) 0.0066(10) -0.0047(9) C5 0.0404(12) 0.0455(12) 0.0467(12) 0.0108(10) 0.0003(10) -0.0067(10) C6 0.0550(15) 0.0542(14) 0.0507(14) 0.0109(11) 0.0130(11) -0.0071(12) C7 0.0747(19) 0.0698(18) 0.0515(15) 0.0247(13) 0.0053(13) -0.0224(15) C8 0.0718(19) 0.0556(15) 0.0617(16) 0.0305(13) -0.0155(14) -0.0088(14) C9 0.0472(14) 0.0525(14) 0.0609(15) 0.0174(12) -0.0102(12) 0.0008(11) N10 0.0401(11) 0.0509(12) 0.0643(13) 0.0128(10) 0.0158(9) -0.0012(9) C11 0.0488(15) 0.0677(17) 0.0658(17) 0.0050(14) 0.0076(13) -0.0030(13) C12 0.0542(16) 0.0662(17) 0.0572(16) 0.0057(13) 0.0052(12) 0.0018(13) C13 0.0640(18) 0.0713(19) 0.0570(16) 0.0023(14) 0.0052(13) 0.0030(14) C14 0.0678(19) 0.0743(19) 0.0550(16) 0.0033(14) 0.0022(14) 0.0062(15) C15 0.0694(19) 0.0705(18) 0.0512(15) 0.0045(13) 0.0034(13) 0.0078(15) C16 0.0637(18) 0.077(2) 0.0608(17) 0.0068(15) 0.0029(14) 0.0060(15) C17 0.0662(19) 0.0728(19) 0.0604(17) 0.0047(14) 0.0059(14) 0.0048(15) C18 0.0675(19) 0.073(2) 0.0654(18) 0.0064(15) 0.0052(15) 0.0053(15) C19 0.0656(19) 0.073(2) 0.0684(19) 0.0046(15) 0.0065(15) 0.0042(15) C20 0.068(2) 0.075(2) 0.074(2) 0.0080(16) 0.0077(16) 0.0053(16) C21 0.068(2) 0.073(2) 0.080(2) 0.0029(17) 0.0102(17) 0.0063(16) C22 0.072(2) 0.085(2) 0.116(3) 0.010(2) 0.019(2) 0.0120(19) C23 0.108(4) 0.110(4) 0.154(5) -0.026(3) 0.054(3) 0.023(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C5 2.027(2) . ? Fe1 C5 2.027(2) 2_666 ? Fe1 C6 2.031(3) 2_666 ? Fe1 C6 2.031(3) . ? Fe1 C8 2.037(3) 2_666 ? Fe1 C8 2.037(3) . ? Fe1 C9 2.040(3) . ? Fe1 C9 2.040(3) 2_666 ? Fe1 C7 2.040(3) . ? Fe1 C7 2.040(3) 2_666 ? O2 C4 1.241(3) . ? O3 C4 1.264(3) . ? C4 C5 1.488(3) . ? C5 C6 1.422(4) . ? C5 C9 1.432(4) . ? C6 C7 1.418(4) . ? C6 H6 0.9800 . ? C7 C8 1.410(5) . ? C7 H7 0.9800 . ? C8 C9 1.417(4) . ? C8 H8 0.9800 . ? C9 H9 0.9800 . ? N10 C11 1.484(4) . ? N10 H10A 0.8900 . ? N10 H10B 0.8900 . ? N10 H10C 0.8900 . ? C11 C12 1.496(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.527(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.506(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.518(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.517(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.510(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.509(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.516(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.504(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.519(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.503(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.498(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24A 1.687(10) . ? C23 C24B 1.690(14) . ? C23 C25B 1.97(3) . ? C24A C25B 0.82(3) . ? C24A C24B 1.146(14) . ? C24A C25A 1.444(11) . ? C24B C25A 1.370(14) . ? C24B C25B 1.51(3) . ? C25A C25B 1.07(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 C5 Fe1 C5 179.998(2) . 2_666 ? C5 Fe1 C6 138.98(10) . 2_666 ? C5 Fe1 C6 41.02(10) 2_666 2_666 ? C5 Fe1 C6 41.02(10) . . ? C5 Fe1 C6 138.98(10) 2_666 . ? C6 Fe1 C6 179.999(1) 2_666 . ? C5 Fe1 C8 111.08(11) . 2_666 ? C5 Fe1 C8 68.91(11) 2_666 2_666 ? C6 Fe1 C8 68.48(13) 2_666 2_666 ? C6 Fe1 C8 111.52(13) . 2_666 ? C5 Fe1 C8 68.92(11) . . ? C5 Fe1 C8 111.09(11) 2_666 . ? C6 Fe1 C8 111.52(13) 2_666 . ? C6 Fe1 C8 68.48(13) . . ? C8 Fe1 C8 180.000(1) 2_666 . ? C5 Fe1 C9 41.22(10) . . ? C5 Fe1 C9 138.78(10) 2_666 . ? C6 Fe1 C9 111.14(12) 2_666 . ? C6 Fe1 C9 68.86(12) . . ? C8 Fe1 C9 139.31(12) 2_666 . ? C8 Fe1 C9 40.69(12) . . ? C5 Fe1 C9 138.78(10) . 2_666 ? C5 Fe1 C9 41.22(10) 2_666 2_666 ? C6 Fe1 C9 68.85(12) 2_666 2_666 ? C6 Fe1 C9 111.15(12) . 2_666 ? C8 Fe1 C9 40.69(12) 2_666 2_666 ? C8 Fe1 C9 139.31(12) . 2_666 ? C9 Fe1 C9 180.0 . 2_666 ? C5 Fe1 C7 68.89(11) . . ? C5 Fe1 C7 111.11(11) 2_666 . ? C6 Fe1 C7 139.23(11) 2_666 . ? C6 Fe1 C7 40.77(11) . . ? C8 Fe1 C7 139.53(14) 2_666 . ? C8 Fe1 C7 40.47(14) . . ? C9 Fe1 C7 68.49(13) . . ? C9 Fe1 C7 111.51(13) 2_666 . ? C5 Fe1 C7 111.11(11) . 2_666 ? C5 Fe1 C7 68.89(11) 2_666 2_666 ? C6 Fe1 C7 40.77(11) 2_666 2_666 ? C6 Fe1 C7 139.23(11) . 2_666 ? C8 Fe1 C7 40.47(14) 2_666 2_666 ? C8 Fe1 C7 139.53(14) . 2_666 ? C9 Fe1 C7 111.51(13) . 2_666 ? C9 Fe1 C7 68.49(13) 2_666 2_666 ? C7 Fe1 C7 180.00(18) . 2_666 ? O2 C4 O3 123.7(2) . . ? O2 C4 C5 118.0(2) . . ? O3 C4 C5 118.3(2) . . ? C6 C5 C9 107.5(2) . . ? C6 C5 C4 127.3(2) . . ? C9 C5 C4 125.0(2) . . ? C6 C5 Fe1 69.64(14) . . ? C9 C5 Fe1 69.85(14) . . ? C4 C5 Fe1 121.80(17) . . ? C7 C6 C5 108.2(3) . . ? C7 C6 Fe1 69.95(16) . . ? C5 C6 Fe1 69.34(14) . . ? C7 C6 H6 125.9 . . ? C5 C6 H6 125.9 . . ? Fe1 C6 H6 125.9 . . ? C8 C7 C6 108.1(3) . . ? C8 C7 Fe1 69.64(16) . . ? C6 C7 Fe1 69.28(15) . . ? C8 C7 H7 126.0 . . ? C6 C7 H7 126.0 . . ? Fe1 C7 H7 126.0 . . ? C7 C8 C9 108.6(2) . . ? C7 C8 Fe1 69.89(15) . . ? C9 C8 Fe1 69.76(15) . . ? C7 C8 H8 125.7 . . ? C9 C8 H8 125.7 . . ? Fe1 C8 H8 125.7 . . ? C8 C9 C5 107.6(3) . . ? C8 C9 Fe1 69.55(15) . . ? C5 C9 Fe1 68.92(13) . . ? C8 C9 H9 126.2 . . ? C5 C9 H9 126.2 . . ? Fe1 C9 H9 126.2 . . ? C11 N10 H10A 109.5 . . ? C11 N10 H10B 109.5 . . ? H10A N10 H10B 109.5 . . ? C11 N10 H10C 109.5 . . ? H10A N10 H10C 109.5 . . ? H10B N10 H10C 109.5 . . ? N10 C11 C12 112.4(2) . . ? N10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? N10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 112.6(2) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 113.0(2) . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 115.1(3) . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14A 108.5 . . ? C13 C14 H14B 108.5 . . ? C15 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C16 C15 C14 113.5(3) . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15B 108.9 . . ? C14 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 115.1(3) . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? C15 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C18 C17 C16 114.1(3) . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17B 108.7 . . ? C16 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 115.3(3) . . ? C17 C18 H18A 108.5 . . ? C19 C18 H18A 108.5 . . ? C17 C18 H18B 108.5 . . ? C19 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C20 C19 C18 114.5(3) . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19B 108.6 . . ? C18 C19 H19B 108.6 . . ? H19A C19 H19B 107.6 . . ? C19 C20 C21 115.6(3) . . ? C19 C20 H20A 108.4 . . ? C21 C20 H20A 108.4 . . ? C19 C20 H20B 108.4 . . ? C21 C20 H20B 108.4 . . ? H20A C20 H20B 107.4 . . ? C22 C21 C20 114.3(3) . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21B 108.7 . . ? C20 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C23 C22 C21 115.7(4) . . ? C23 C22 H22A 108.3 . . ? C21 C22 H22A 108.3 . . ? C23 C22 H22B 108.3 . . ? C21 C22 H22B 108.3 . . ? H22A C22 H22B 107.4 . . ? C22 C23 C24A 101.3(5) . . ? C22 C23 C24B 125.5(6) . . ? C24A C23 C24B 39.7(5) . . ? C22 C23 C25B 116.1(11) . . ? C24A C23 C25B 24.4(9) . . ? C24B C23 C25B 47.8(10) . . ? C25B C24A C24B 99(3) . . ? C25B C24A C25A 47(2) . . ? C24B C24A C25A 62.6(8) . . ? C25B C24A C23 98(2) . . ? C24B C24A C23 70.3(8) . . ? C25A C24A C23 110.4(6) . . ? C24A C24B C25A 69.4(9) . . ? C24A C24B C25B 32.7(13) . . ? C25A C24B C25B 43.5(12) . . ? C24A C24B C23 70.0(8) . . ? C25A C24B C23 114.2(10) . . ? C25B C24B C23 76.0(14) . . ? C25B C25A C24B 75.1(18) . . ? C25B C25A C24A 34.3(18) . . ? C24B C25A C24A 48.0(6) . . ? C24A C25B C25A 98(3) . . ? C24A C25B C24B 48.8(19) . . ? C25A C25B C24B 61.4(17) . . ? C24A C25B C23 58(2) . . ? C25A C25B C23 112(2) . . ? C24B C25B C23 56.2(11) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10A O3 0.89 1.92 2.777(3) 161.3 1_655 N10 H10B O2 0.89 1.84 2.725(3) 170.2 2_656 N10 H10C O3 0.89 1.88 2.737(3) 161.3 2_756 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.777 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.107