Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Dr Petr Stepnicka' _publ_contact_author_address ; Department of Inorganic Chemistry Charles University, Faculty of Science Hlavova 2030 Prague 12840 CZECH REPUBLIC ; _publ_contact_author_email STEPNIC@NATUR.CUNI.CZ _publ_section_title ; Preparation and hydrogen bonding in ferrocenecarboxamides substituted with 2-hydroxyethyl groups at the amide nitrogen atoms ; loop_ _publ_author_name 'P. Stepnicka' 'Ivana Cisarova' data_ps1058aa _database_code_depnum_ccdc_archive 'CCDC 254368' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(2-hydroxyethyl)ferrocene carboxamide ; _chemical_name_common 'N-(2-hydroxyethyl)ferrocene carboxamide' _chemical_formula_moiety 'C13 H15 Fe N O2' _chemical_formula_sum 'C13 H15 Fe N O2' _chemical_formula_weight 273.11 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 monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.0685(2) _cell_length_b 12.7121(3) _cell_length_c 10.0790(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.5150(10) _cell_angle_gamma 90.00 _cell_volume 1164.22(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2776 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 1.283 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.781 _exptl_absorpt_correction_T_max 0.880 _exptl_absorpt_process_details ; SORTAV routine Blessing, R. H. (1997). J. Appl. Cryst. 30, 421--426 ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\w and \p scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_reflns_number 20163 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.43 _reflns_number_total 2642 _reflns_number_gt 2312 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _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^)+(0.0313P)^2^+0.6664P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2642 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe Fe 0.63491(2) -0.017365(18) 0.30408(2) 0.01752(9) Uani 1 1 d . . . N N 0.82679(16) 0.25900(11) 0.41031(16) 0.0228(3) Uani 1 1 d . . . H91 H 0.808(2) 0.2514(17) 0.477(2) 0.030(6) Uiso 1 1 d . . . O1 O 0.77541(14) 0.22107(10) 0.17560(12) 0.0257(3) Uani 1 1 d . . . O2 O 0.93954(16) 0.43488(11) 0.62363(15) 0.0336(3) Uani 1 1 d . . . H92 H 0.884(2) 0.3987(19) 0.642(2) 0.039(6) Uiso 1 1 d . . . C1 C 0.62631(17) 0.14158(12) 0.27566(17) 0.0183(3) Uani 1 1 d . . . C2 C 0.58237(18) 0.11326(13) 0.38888(17) 0.0203(3) Uani 1 1 d . . . H2 H 0.6276 0.1345 0.4866 0.024 Uiso 1 1 calc R . . C3 C 0.45692(18) 0.04669(14) 0.32418(18) 0.0232(3) Uani 1 1 d . . . H3 H 0.4052 0.0176 0.3725 0.028 Uiso 1 1 calc R . . C4 C 0.42395(18) 0.03216(14) 0.17312(18) 0.0237(4) Uani 1 1 d . . . H4 H 0.3478 -0.0085 0.1061 0.028 Uiso 1 1 calc R . . C5 C 0.52780(18) 0.09067(13) 0.14301(17) 0.0217(3) Uani 1 1 d . . . H5 H 0.5313 0.0952 0.0525 0.026 Uiso 1 1 calc R . . C6 C 0.84784(18) -0.06491(14) 0.36420(19) 0.0250(4) Uani 1 1 d . . . H6 H 0.9272 -0.0216 0.3780 0.030 Uiso 1 1 calc R . . C7 C 0.80072(19) -0.09374(14) 0.47402(19) 0.0278(4) Uani 1 1 d . . . H7 H 0.8437 -0.0725 0.5719 0.033 Uiso 1 1 calc R . . C8 C 0.6767(2) -0.16060(14) 0.4072(2) 0.0295(4) Uani 1 1 d . . . H8 H 0.6241 -0.1911 0.4538 0.035 Uiso 1 1 calc R . . C9 C 0.6466(2) -0.17298(14) 0.2570(2) 0.0288(4) Uani 1 1 d . . . H9 H 0.5709 -0.2129 0.1881 0.035 Uiso 1 1 calc R . . C10 C 0.75243(19) -0.11385(14) 0.23016(19) 0.0250(4) Uani 1 1 d . . . H10 H 0.7581 -0.1082 0.1408 0.030 Uiso 1 1 calc R . . C11 C 0.74812(18) 0.20960(12) 0.28450(16) 0.0189(3) Uani 1 1 d . . . C12 C 0.9509(2) 0.32661(14) 0.4293(2) 0.0271(4) Uani 1 1 d . . . H12A H 0.9158 0.3860 0.3626 0.033 Uiso 1 1 calc R . . H12B H 1.0199 0.2875 0.4046 0.033 Uiso 1 1 calc R . . C13 C 1.02834(19) 0.36621(15) 0.5847(2) 0.0284(4) Uani 1 1 d . . . H13A H 1.0573 0.3066 0.6513 0.034 Uiso 1 1 calc R . . H13B H 1.1171 0.4031 0.5964 0.034 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 Fe 0.01892(13) 0.01511(13) 0.01747(13) -0.00070(8) 0.00684(10) -0.00095(9) N 0.0321(8) 0.0226(8) 0.0212(7) -0.0030(6) 0.0186(6) -0.0062(6) O1 0.0398(7) 0.0238(6) 0.0214(6) 0.0017(5) 0.0206(5) 0.0007(5) O2 0.0472(8) 0.0254(7) 0.0391(8) -0.0090(6) 0.0288(7) -0.0100(6) C1 0.0254(8) 0.0134(8) 0.0178(7) 0.0007(6) 0.0108(7) 0.0025(6) C2 0.0270(8) 0.0180(8) 0.0184(7) -0.0008(6) 0.0124(7) -0.0002(7) C3 0.0219(8) 0.0253(9) 0.0250(8) 0.0005(7) 0.0125(7) 0.0014(7) C4 0.0176(8) 0.0270(9) 0.0220(8) -0.0022(7) 0.0044(7) 0.0011(7) C5 0.0254(8) 0.0224(9) 0.0160(7) 0.0013(6) 0.0077(7) 0.0053(7) C6 0.0190(8) 0.0250(9) 0.0275(9) 0.0036(7) 0.0069(7) 0.0014(7) C7 0.0282(9) 0.0289(10) 0.0229(8) 0.0084(7) 0.0076(7) 0.0060(7) C8 0.0335(10) 0.0185(9) 0.0404(10) 0.0104(7) 0.0196(8) 0.0036(7) C9 0.0302(9) 0.0147(8) 0.0406(10) -0.0059(7) 0.0144(8) -0.0015(7) C10 0.0258(9) 0.0216(9) 0.0280(9) -0.0010(7) 0.0121(7) 0.0050(7) C11 0.0277(8) 0.0146(8) 0.0180(7) 0.0023(6) 0.0133(7) 0.0050(6) C12 0.0331(10) 0.0241(9) 0.0338(10) -0.0041(7) 0.0235(8) -0.0072(7) C13 0.0261(9) 0.0281(10) 0.0314(9) -0.0011(8) 0.0126(8) -0.0043(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe C1 2.0373(16) . ? Fe C2 2.0390(16) . ? Fe C5 2.0435(16) . ? Fe C8 2.0486(17) . ? Fe C7 2.0494(17) . ? Fe C9 2.0494(17) . ? Fe C6 2.0516(17) . ? Fe C10 2.0540(17) . ? Fe C3 2.0564(17) . ? Fe C4 2.0579(17) . ? N C11 1.328(2) . ? N C12 1.460(2) . ? N H91 0.78(2) . ? O1 C11 1.2495(18) . ? O2 C13 1.421(2) . ? O2 H92 0.81(2) . ? C1 C5 1.431(2) . ? C1 C2 1.436(2) . ? C1 C11 1.472(2) . ? C2 C3 1.424(2) . ? C2 H2 0.9300 . ? C3 C4 1.424(2) . ? C3 H3 0.9300 . ? C4 C5 1.418(2) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C10 1.420(2) . ? C6 C7 1.427(2) . ? C6 H6 0.9300 . ? C7 C8 1.418(3) . ? C7 H7 0.9300 . ? C8 C9 1.419(3) . ? C8 H8 0.9300 . ? C9 C10 1.422(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C12 C13 1.504(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Fe C2 41.26(6) . . ? C1 Fe C5 41.05(6) . . ? C2 Fe C5 69.04(6) . . ? C1 Fe C8 160.03(7) . . ? C2 Fe C8 123.00(7) . . ? C5 Fe C8 157.40(7) . . ? C1 Fe C7 123.87(7) . . ? C2 Fe C7 107.49(7) . . ? C5 Fe C7 160.64(7) . . ? C8 Fe C7 40.49(7) . . ? C1 Fe C9 158.11(7) . . ? C2 Fe C9 159.11(7) . . ? C5 Fe C9 121.88(7) . . ? C8 Fe C9 40.52(8) . . ? C7 Fe C9 68.21(8) . . ? C1 Fe C6 108.02(7) . . ? C2 Fe C6 122.88(7) . . ? C5 Fe C6 124.01(7) . . ? C8 Fe C6 68.19(7) . . ? C7 Fe C6 40.73(7) . . ? C9 Fe C6 68.10(7) . . ? C1 Fe C10 122.51(7) . . ? C2 Fe C10 158.81(7) . . ? C5 Fe C10 107.61(7) . . ? C8 Fe C10 68.22(7) . . ? C7 Fe C10 68.36(7) . . ? C9 Fe C10 40.54(7) . . ? C6 Fe C10 40.48(7) . . ? C1 Fe C3 68.60(7) . . ? C2 Fe C3 40.69(7) . . ? C5 Fe C3 68.17(7) . . ? C8 Fe C3 107.39(7) . . ? C7 Fe C3 122.41(7) . . ? C9 Fe C3 122.99(7) . . ? C6 Fe C3 158.70(7) . . ? C10 Fe C3 159.20(7) . . ? C1 Fe C4 68.70(7) . . ? C2 Fe C4 68.73(7) . . ? C5 Fe C4 40.46(7) . . ? C8 Fe C4 121.80(7) . . ? C7 Fe C4 157.69(7) . . ? C9 Fe C4 107.05(7) . . ? C6 Fe C4 159.73(7) . . ? C10 Fe C4 123.14(7) . . ? C3 Fe C4 40.49(7) . . ? C11 N C12 121.89(14) . . ? C11 N H91 119.7(15) . . ? C12 N H91 118.4(15) . . ? C13 O2 H92 107.4(17) . . ? C5 C1 C2 107.59(14) . . ? C5 C1 C11 123.13(14) . . ? C2 C1 C11 129.28(14) . . ? C5 C1 Fe 69.71(9) . . ? C2 C1 Fe 69.43(9) . . ? C11 C1 Fe 126.18(11) . . ? C3 C2 C1 107.53(14) . . ? C3 C2 Fe 70.31(9) . . ? C1 C2 Fe 69.31(9) . . ? C3 C2 H2 126.2 . . ? C1 C2 H2 126.2 . . ? Fe C2 H2 125.7 . . ? C4 C3 C2 108.60(15) . . ? C4 C3 Fe 69.81(9) . . ? C2 C3 Fe 69.00(9) . . ? C4 C3 H3 125.7 . . ? C2 C3 H3 125.7 . . ? Fe C3 H3 127.1 . . ? C5 C4 C3 107.88(15) . . ? C5 C4 Fe 69.22(9) . . ? C3 C4 Fe 69.70(9) . . ? C5 C4 H4 126.1 . . ? C3 C4 H4 126.1 . . ? Fe C4 H4 126.6 . . ? C4 C5 C1 108.39(14) . . ? C4 C5 Fe 70.31(9) . . ? C1 C5 Fe 69.24(9) . . ? C4 C5 H5 125.8 . . ? C1 C5 H5 125.8 . . ? Fe C5 H5 126.2 . . ? C10 C6 C7 108.10(16) . . ? C10 C6 Fe 69.85(10) . . ? C7 C6 Fe 69.55(10) . . ? C10 C6 H6 125.9 . . ? C7 C6 H6 125.9 . . ? Fe C6 H6 126.2 . . ? C8 C7 C6 107.75(16) . . ? C8 C7 Fe 69.72(10) . . ? C6 C7 Fe 69.72(9) . . ? C8 C7 H7 126.1 . . ? C6 C7 H7 126.1 . . ? Fe C7 H7 126.0 . . ? C7 C8 C9 108.19(16) . . ? C7 C8 Fe 69.78(10) . . ? C9 C8 Fe 69.77(10) . . ? C7 C8 H8 125.9 . . ? C9 C8 H8 125.9 . . ? Fe C8 H8 126.1 . . ? C8 C9 C10 108.17(16) . . ? C8 C9 Fe 69.71(10) . . ? C10 C9 Fe 69.90(10) . . ? C8 C9 H9 125.9 . . ? C10 C9 H9 125.9 . . ? Fe C9 H9 126.1 . . ? C6 C10 C9 107.80(16) . . ? C6 C10 Fe 69.67(10) . . ? C9 C10 Fe 69.56(10) . . ? C6 C10 H10 126.1 . . ? C9 C10 H10 126.1 . . ? Fe C10 H10 126.2 . . ? O1 C11 N 121.14(15) . . ? O1 C11 C1 120.54(14) . . ? N C11 C1 118.31(13) . . ? N C12 C13 111.35(14) . . ? N C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? N C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? O2 C13 C12 112.82(15) . . ? O2 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? O2 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.398 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.057 data_ps1061b _database_code_depnum_ccdc_archive 'CCDC 254369' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-hydroxyethyl)ferrocene 1,1-dicarboxamide ; _chemical_name_common "N,N'-bis(2-hydroxyethyl)ferrocene 1,1-dicarboxamide" _chemical_formula_moiety 'C16 H20 Fe N2 O4' _chemical_formula_sum 'C16 H20 Fe N2 O4' _chemical_formula_weight 360.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.0886(2) _cell_length_b 10.0348(1) _cell_length_c 16.7610(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1528.64(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13987 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 1.009 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.694 _exptl_absorpt_correction_T_max 0.796 _exptl_absorpt_process_details ; Gaussian absorption correction from the indexed crystal shape incorporated in the diffractometer software used ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\w and \p scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_reflns_number 21614 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3489 _reflns_number_gt 3421 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _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^)+(0.0276P)^2^+0.3688P] 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 mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.013(9) _chemical_absolute_configuration ad _refine_ls_number_reflns 3489 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0196 _refine_ls_R_factor_gt 0.0191 _refine_ls_wR_factor_ref 0.0502 _refine_ls_wR_factor_gt 0.0499 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe Fe 0.151791(19) 0.590285(17) 0.084298(11) 0.01370(6) Uani 1 1 d . . . O1 O 0.56044(11) 0.57468(10) 0.13444(7) 0.0240(2) Uani 1 1 d . . . O2 O 0.36687(13) 0.28755(14) 0.27421(7) 0.0323(3) Uani 1 1 d . . . H92 H 0.379(3) 0.225(3) 0.2962(16) 0.063(8) Uiso 1 1 d . . . O3 O -0.07779(11) 0.28285(10) 0.08631(7) 0.0264(2) Uani 1 1 d . . . O4 O 0.34039(13) 0.12304(11) 0.06021(7) 0.0276(2) Uani 1 1 d . . . H94 H 0.366(3) 0.136(2) 0.0148(15) 0.053(7) Uiso 1 1 d . . . N1 N 0.47406(13) 0.36589(12) 0.11931(7) 0.0185(2) Uani 1 1 d . . . H91 H 0.410(2) 0.3149(18) 0.0991(12) 0.027(5) Uiso 1 1 d . . . N2 N 0.12163(14) 0.24180(12) 0.16296(7) 0.0203(2) Uani 1 1 d . . . H93 H 0.183(2) 0.2728(19) 0.1927(11) 0.022(5) Uiso 1 1 d . . . C1 C 0.35848(15) 0.54502(13) 0.04695(8) 0.0157(2) Uani 1 1 d . . . C2 C 0.32858(15) 0.68359(14) 0.03324(8) 0.0180(3) Uani 1 1 d . . . H2 H 0.3808 0.7550 0.0545 0.022 Uiso 1 1 calc R . . C3 C 0.20559(16) 0.69241(15) -0.01828(8) 0.0197(3) Uani 1 1 d . . . H3 H 0.1624 0.7707 -0.0365 0.024 Uiso 1 1 calc R . . C4 C 0.15939(17) 0.56059(14) -0.03743(8) 0.0191(3) Uani 1 1 d . . . H4 H 0.0813 0.5382 -0.0707 0.023 Uiso 1 1 calc R . . C5 C 0.25231(16) 0.46964(14) 0.00270(8) 0.0174(3) Uani 1 1 d . . . H5 H 0.2457 0.3772 0.0007 0.021 Uiso 1 1 calc R . . C6 C 0.03047(15) 0.46642(14) 0.15357(8) 0.0172(3) Uani 1 1 d . . . C7 C 0.13964(17) 0.53300(14) 0.20098(8) 0.0188(3) Uani 1 1 d . . . H7 H 0.2141 0.4924 0.2303 0.023 Uiso 1 1 calc R . . C8 C 0.11332(16) 0.67213(15) 0.19502(9) 0.0213(3) Uani 1 1 d . . . H8 H 0.1680 0.7386 0.2198 0.026 Uiso 1 1 calc R . . C9 C -0.01089(15) 0.69272(15) 0.14476(9) 0.0200(3) Uani 1 1 d . . . H9 H -0.0510 0.7748 0.1310 0.024 Uiso 1 1 calc R . . C10 C -0.06269(14) 0.56703(14) 0.11939(9) 0.0185(3) Uani 1 1 d . . . H10 H -0.1431 0.5520 0.0863 0.022 Uiso 1 1 calc R . . C11 C 0.47176(15) 0.49646(13) 0.10343(8) 0.0164(3) Uani 1 1 d . . . C12 C 0.56983(17) 0.31200(17) 0.18105(9) 0.0251(3) Uani 1 1 d . . . H12A H 0.6674 0.3501 0.1756 0.030 Uiso 1 1 calc R . . H12B H 0.5780 0.2162 0.1745 0.030 Uiso 1 1 calc R . . C13 C 0.50995(18) 0.34301(18) 0.26349(9) 0.0292(3) Uani 1 1 d . . . H13A H 0.5760 0.3071 0.3035 0.035 Uiso 1 1 calc R . . H13B H 0.5053 0.4388 0.2707 0.035 Uiso 1 1 calc R . . C14 C 0.02048(15) 0.32355(14) 0.13202(8) 0.0185(3) Uani 1 1 d . . . C15 C 0.12641(17) 0.10092(14) 0.14309(9) 0.0258(3) Uani 1 1 d . . . H15A H 0.0273 0.0651 0.1444 0.031 Uiso 1 1 calc R . . H15B H 0.1840 0.0543 0.1830 0.031 Uiso 1 1 calc R . . C16 C 0.19266(16) 0.07591(15) 0.06148(9) 0.0257(3) Uani 1 1 d . . . H16A H 0.1908 -0.0187 0.0497 0.031 Uiso 1 1 calc R . . H16B H 0.1354 0.1217 0.0211 0.031 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 Fe 0.01241(8) 0.01476(8) 0.01392(9) -0.00092(7) 0.00055(7) 0.00053(7) O1 0.0198(5) 0.0231(5) 0.0293(5) -0.0004(4) -0.0055(4) -0.0024(4) O2 0.0257(6) 0.0451(7) 0.0261(5) 0.0143(5) -0.0007(5) 0.0049(5) O3 0.0227(5) 0.0238(5) 0.0326(6) 0.0005(5) -0.0064(5) -0.0049(4) O4 0.0238(5) 0.0322(6) 0.0268(6) -0.0064(4) 0.0037(5) -0.0004(5) N1 0.0184(5) 0.0191(5) 0.0180(6) 0.0013(5) -0.0030(5) 0.0017(5) N2 0.0216(6) 0.0206(6) 0.0186(6) 0.0014(5) 0.0016(5) 0.0012(5) C1 0.0145(6) 0.0175(6) 0.0152(6) 0.0006(4) 0.0029(5) 0.0018(5) C2 0.0165(6) 0.0178(6) 0.0197(6) 0.0028(5) 0.0026(5) -0.0010(5) C3 0.0200(6) 0.0206(6) 0.0184(6) 0.0061(5) 0.0009(5) 0.0025(5) C4 0.0194(6) 0.0261(7) 0.0119(6) -0.0002(5) -0.0008(5) 0.0004(6) C5 0.0201(6) 0.0174(6) 0.0148(6) -0.0027(5) 0.0023(5) 0.0021(5) C6 0.0144(6) 0.0216(6) 0.0156(6) 0.0018(5) 0.0029(5) 0.0007(5) C7 0.0165(6) 0.0270(7) 0.0131(6) -0.0018(5) 0.0006(6) 0.0017(6) C8 0.0203(7) 0.0261(7) 0.0176(6) -0.0073(6) 0.0016(5) 0.0001(5) C9 0.0166(6) 0.0214(7) 0.0220(7) -0.0045(5) 0.0031(5) 0.0046(5) C10 0.0119(6) 0.0231(7) 0.0205(7) -0.0013(5) 0.0015(5) 0.0014(5) C11 0.0144(6) 0.0191(6) 0.0157(7) -0.0001(5) 0.0030(5) 0.0008(5) C12 0.0210(7) 0.0293(8) 0.0250(8) 0.0072(6) -0.0033(6) 0.0061(6) C13 0.0250(7) 0.0417(9) 0.0209(8) 0.0070(7) -0.0069(6) 0.0011(6) C14 0.0173(6) 0.0210(6) 0.0171(6) 0.0036(5) 0.0040(5) -0.0019(5) C15 0.0292(7) 0.0194(6) 0.0287(8) 0.0044(6) 0.0048(6) 0.0020(6) C16 0.0264(7) 0.0208(7) 0.0299(8) -0.0047(6) 0.0000(6) -0.0023(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe C6 2.0270(14) . ? Fe C1 2.0315(14) . ? Fe C7 2.0415(14) . ? Fe C5 2.0423(13) . ? Fe C2 2.0472(14) . ? Fe C10 2.0495(13) . ? Fe C8 2.0593(14) . ? Fe C3 2.0603(14) . ? Fe C4 2.0631(13) . ? Fe C9 2.0663(14) . ? O1 C11 1.2392(17) . ? O2 C13 1.426(2) . ? O2 H92 0.74(3) . ? O3 C14 1.2456(18) . ? O4 C16 1.4237(18) . ? O4 H94 0.81(2) . ? N1 C11 1.3372(18) . ? N1 C12 1.4564(18) . ? N1 H91 0.84(2) . ? N2 C14 1.3368(19) . ? N2 C15 1.4531(19) . ? N2 H93 0.811(19) . ? C1 C5 1.433(2) . ? C1 C2 1.4354(18) . ? C1 C11 1.4811(19) . ? C2 C3 1.415(2) . ? C2 H2 0.9300 . ? C3 C4 1.424(2) . ? C3 H3 0.9300 . ? C4 C5 1.414(2) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.436(2) . ? C6 C10 1.4368(19) . ? C6 C14 1.4812(19) . ? C7 C8 1.420(2) . ? C7 H7 0.9300 . ? C8 C9 1.424(2) . ? C8 H8 0.9300 . ? C9 C10 1.412(2) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C12 C13 1.517(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C15 C16 1.515(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 Fe C1 122.85(5) . . ? C6 Fe C7 41.34(6) . . ? C1 Fe C7 106.40(6) . . ? C6 Fe C5 105.27(6) . . ? C1 Fe C5 41.19(6) . . ? C7 Fe C5 119.92(6) . . ? C6 Fe C2 161.24(6) . . ? C1 Fe C2 41.21(5) . . ? C7 Fe C2 124.87(6) . . ? C5 Fe C2 68.90(6) . . ? C6 Fe C10 41.27(5) . . ? C1 Fe C10 160.47(5) . . ? C7 Fe C10 68.99(6) . . ? C5 Fe C10 123.38(6) . . ? C2 Fe C10 156.72(6) . . ? C6 Fe C8 68.65(6) . . ? C1 Fe C8 121.59(5) . . ? C7 Fe C8 40.52(6) . . ? C5 Fe C8 156.33(6) . . ? C2 Fe C8 109.13(6) . . ? C10 Fe C8 67.99(6) . . ? C6 Fe C3 155.79(6) . . ? C1 Fe C3 68.57(5) . . ? C7 Fe C3 162.23(6) . . ? C5 Fe C3 68.28(6) . . ? C2 Fe C3 40.31(6) . . ? C10 Fe C3 121.46(6) . . ? C8 Fe C3 126.44(6) . . ? C6 Fe C4 119.74(6) . . ? C1 Fe C4 68.41(6) . . ? C7 Fe C4 155.31(5) . . ? C5 Fe C4 40.28(6) . . ? C2 Fe C4 68.06(6) . . ? C10 Fe C4 107.41(6) . . ? C8 Fe C4 162.65(6) . . ? C3 Fe C4 40.42(5) . . ? C6 Fe C9 68.59(6) . . ? C1 Fe C9 157.52(6) . . ? C7 Fe C9 68.38(6) . . ? C5 Fe C9 160.63(6) . . ? C2 Fe C9 122.63(6) . . ? C10 Fe C9 40.12(6) . . ? C8 Fe C9 40.37(6) . . ? C3 Fe C9 109.37(6) . . ? C4 Fe C9 125.51(6) . . ? C13 O2 H92 105(2) . . ? C16 O4 H94 109.7(19) . . ? C11 N1 C12 120.97(13) . . ? C11 N1 H91 120.3(13) . . ? C12 N1 H91 118.0(13) . . ? C14 N2 C15 121.92(13) . . ? C14 N2 H93 118.5(13) . . ? C15 N2 H93 119.6(13) . . ? C5 C1 C2 107.52(12) . . ? C5 C1 C11 128.70(12) . . ? C2 C1 C11 123.55(12) . . ? C5 C1 Fe 69.81(8) . . ? C2 C1 Fe 69.98(8) . . ? C11 C1 Fe 121.29(9) . . ? C3 C2 C1 107.92(12) . . ? C3 C2 Fe 70.35(8) . . ? C1 C2 Fe 68.81(8) . . ? C3 C2 H2 126.0 . . ? C1 C2 H2 126.0 . . ? Fe C2 H2 126.4 . . ? C2 C3 C4 108.20(12) . . ? C2 C3 Fe 69.35(8) . . ? C4 C3 Fe 69.90(8) . . ? C2 C3 H3 125.9 . . ? C4 C3 H3 125.9 . . ? Fe C3 H3 126.4 . . ? C5 C4 C3 108.43(12) . . ? C5 C4 Fe 69.07(7) . . ? C3 C4 Fe 69.69(8) . . ? C5 C4 H4 125.8 . . ? C3 C4 H4 125.8 . . ? Fe C4 H4 127.0 . . ? C4 C5 C1 107.92(12) . . ? C4 C5 Fe 70.65(8) . . ? C1 C5 Fe 69.00(8) . . ? C4 C5 H5 126.0 . . ? C1 C5 H5 126.0 . . ? Fe C5 H5 125.9 . . ? C7 C6 C10 107.51(12) . . ? C7 C6 C14 128.87(13) . . ? C10 C6 C14 123.14(13) . . ? C7 C6 Fe 69.87(8) . . ? C10 C6 Fe 70.20(8) . . ? C14 C6 Fe 119.16(10) . . ? C8 C7 C6 107.58(13) . . ? C8 C7 Fe 70.42(9) . . ? C6 C7 Fe 68.79(8) . . ? C8 C7 H7 126.2 . . ? C6 C7 H7 126.2 . . ? Fe C7 H7 126.1 . . ? C7 C8 C9 108.54(13) . . ? C7 C8 Fe 69.07(8) . . ? C9 C8 Fe 70.08(8) . . ? C7 C8 H8 125.7 . . ? C9 C8 H8 125.7 . . ? Fe C8 H8 126.7 . . ? C10 C9 C8 108.24(13) . . ? C10 C9 Fe 69.30(8) . . ? C8 C9 Fe 69.55(8) . . ? C10 C9 H9 125.9 . . ? C8 C9 H9 125.9 . . ? Fe C9 H9 126.8 . . ? C9 C10 C6 108.13(12) . . ? C9 C10 Fe 70.58(8) . . ? C6 C10 Fe 68.53(7) . . ? C9 C10 H10 125.9 . . ? C6 C10 H10 125.9 . . ? Fe C10 H10 126.5 . . ? O1 C11 N1 121.80(13) . . ? O1 C11 C1 120.79(12) . . ? N1 C11 C1 117.41(12) . . ? N1 C12 C13 110.89(12) . . ? N1 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? O2 C13 C12 111.22(13) . . ? O2 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? O2 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? O3 C14 N2 122.04(13) . . ? O3 C14 C6 120.75(13) . . ? N2 C14 C6 117.20(13) . . ? N2 C15 C16 112.33(12) . . ? N2 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? N2 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.9 . . ? O4 C16 C15 109.47(13) . . ? O4 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? O4 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.269 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.041 data_ps1063 _database_code_depnum_ccdc_archive 'CCDC 254370' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-bis(2-hydroxyethyl)ferrocene carboxamide ; _chemical_name_common 'N,N-bis(2-hydroxyethyl)ferrocene carboxamide' _chemical_formula_moiety 'C15 H19 Fe N O3' _chemical_formula_sum 'C15 H19 Fe N O3' _chemical_formula_weight 317.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.6970(2) _cell_length_b 10.0170(2) _cell_length_c 22.0150(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.601(1) _cell_angle_gamma 90.00 _cell_volume 2797.11(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 28879 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 1.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_process_details ; SORTAV routine Blessing, R. H. (1997). J. Appl. Cryst. 30, 421--426 ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\w and \p scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_reflns_number 43350 _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.51 _reflns_number_total 6401 _reflns_number_gt 5154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _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^)+(0.0414P)^2^+8.7975P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6401 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.62530(4) 0.01354(5) 0.15040(2) 0.02535(13) Uani 1 1 d . A . N1 N 0.3736(3) 0.2408(3) 0.0816(2) 0.0626(13) Uani 1 1 d . . . O1 O 0.3564(2) 0.0225(3) 0.10102(18) 0.0543(9) Uani 1 1 d . . . O2 O 0.4960(3) 0.5742(3) 0.08881(19) 0.0684(11) Uani 1 1 d . A . H91 H 0.4610 0.6528 0.0961 0.103 Uiso 1 1 d R . . C1 C 0.5289(3) 0.0963(3) 0.08372(16) 0.0278(7) Uani 1 1 d . . . C2 C 0.6176(3) 0.1811(4) 0.09822(17) 0.0327(8) Uani 1 1 d . A . H2 H 0.6146 0.2682 0.1128 0.039 Uiso 1 1 calc R . . C3 C 0.7107(3) 0.1091(5) 0.08649(19) 0.0433(10) Uani 1 1 d . . . H3 H 0.7793 0.1409 0.0916 0.052 Uiso 1 1 calc R A . C4 C 0.6811(3) -0.0194(5) 0.06575(17) 0.0452(11) Uani 1 1 d . A . H4 H 0.7271 -0.0863 0.0546 0.054 Uiso 1 1 calc R . . C5 C 0.5702(3) -0.0298(4) 0.06469(16) 0.0381(9) Uani 1 1 d . A . H5 H 0.5309 -0.1049 0.0536 0.046 Uiso 1 1 calc R . . C6 C 0.5364(3) -0.0277(5) 0.22275(18) 0.0465(10) Uani 1 1 d . . . H6 H 0.4636 -0.0188 0.2236 0.056 Uiso 1 1 calc R A . C7 C 0.6110(3) 0.0717(4) 0.23839(17) 0.0417(9) Uani 1 1 d . A . H7 H 0.5961 0.1576 0.2515 0.050 Uiso 1 1 calc R . . C8 C 0.7127(3) 0.0185(4) 0.23072(17) 0.0391(9) Uani 1 1 d . . . H8 H 0.7763 0.0631 0.2376 0.047 Uiso 1 1 calc R A . C9 C 0.7000(3) -0.1154(4) 0.21051(17) 0.0393(9) Uani 1 1 d . A . H9 H 0.7542 -0.1742 0.2021 0.047 Uiso 1 1 calc R . . C10 C 0.5915(3) -0.1438(4) 0.20544(18) 0.0431(9) Uani 1 1 d . A . H10 H 0.5612 -0.2243 0.1930 0.052 Uiso 1 1 calc R . . C11 C 0.4143(3) 0.1177(3) 0.0898(2) 0.0381(9) Uani 1 1 d . A . C12 C 0.4266(3) 0.3604(4) 0.0610(2) 0.0411(10) Uani 1 1 d . A . H12A H 0.3826 0.4034 0.0295 0.049 Uiso 1 1 calc R . . H12B H 0.4923 0.3353 0.0434 0.049 Uiso 1 1 calc R . . C13 C 0.4491(4) 0.4581(4) 0.1122(3) 0.0579(13) Uani 1 1 d . . . H13A H 0.3841 0.4813 0.1311 0.070 Uiso 1 1 calc R A . H13B H 0.4964 0.4177 0.1428 0.070 Uiso 1 1 calc R . . C14A C 0.2651(7) 0.2636(8) 0.1142(5) 0.0326(16) Uani 0.50 1 d P A 1 H14A H 0.2569 0.2019 0.1476 0.039 Uiso 0.50 1 calc PR A 1 H14B H 0.2582 0.3545 0.1287 0.039 Uiso 0.50 1 calc PR A 1 C15A C 0.1894(7) 0.2343(7) 0.0619(4) 0.0344(16) Uani 0.50 1 d P A 1 H15A H 0.2058 0.2898 0.0275 0.041 Uiso 0.50 1 calc PR A 1 H15B H 0.1959 0.1416 0.0499 0.041 Uiso 0.50 1 calc PR A 1 O3A O 0.0839(4) 0.2603(5) 0.0791(3) 0.0478(16) Uani 0.50 1 d P A 1 H92A H 0.0857 0.3336 0.1107 0.072 Uiso 0.50 1 d PR A 1 C14B C 0.2571(5) 0.2477(6) 0.0713(3) 0.0189(12) Uani 0.50 1 d P A 2 H14C H 0.2303 0.1698 0.0495 0.023 Uiso 0.50 1 calc PR A 2 H14D H 0.2363 0.3274 0.0489 0.023 Uiso 0.50 1 calc PR A 2 C15B C 0.2184(6) 0.2516(7) 0.1361(4) 0.0262(14) Uani 0.50 1 d P A 2 H15C H 0.2370 0.1686 0.1567 0.031 Uiso 0.50 1 calc PR A 2 H15D H 0.2533 0.3239 0.1584 0.031 Uiso 0.50 1 calc PR A 2 O3B O 0.1074(4) 0.2701(4) 0.1363(2) 0.0279(10) Uani 0.50 1 d P A 2 H92B H 0.0854 0.3334 0.1102 0.042 Uiso 0.50 1 d PR A 2 Fe2 Fe 0.14477(4) 0.01712(5) 0.34941(2) 0.02448(13) Uani 1 1 d . . . N2 N -0.0938(2) 0.2398(3) 0.42711(16) 0.0361(7) Uani 1 1 d . . . O21 O -0.1100(2) 0.0204(2) 0.40828(15) 0.0406(7) Uani 1 1 d . . . O22 O 0.0337(2) 0.5651(3) 0.40036(18) 0.0602(10) Uani 1 1 d . . . H93 H -0.0063 0.6411 0.4017 0.090 Uiso 1 1 d R . . O23 O -0.3693(2) 0.2683(3) 0.36408(16) 0.0498(8) Uani 1 1 d . . . H94 H -0.3803 0.3667 0.3729 0.075 Uiso 1 1 d R . . C21 C 0.0648(3) 0.1011(3) 0.41804(15) 0.0259(7) Uani 1 1 d . . . C22 C 0.1472(3) 0.1876(3) 0.39971(16) 0.0290(7) Uani 1 1 d . . . H22 H 0.1387 0.2738 0.3845 0.035 Uiso 1 1 calc R . . C23 C 0.2444(3) 0.1189(4) 0.40875(17) 0.0349(8) Uani 1 1 d . . . H23 H 0.3106 0.1525 0.4006 0.042 Uiso 1 1 calc R . . C24 C 0.2238(3) -0.0083(4) 0.43196(16) 0.0366(9) Uani 1 1 d . . . H24 H 0.2741 -0.0731 0.4420 0.044 Uiso 1 1 calc R . . C25 C 0.1139(3) -0.0214(4) 0.43757(16) 0.0324(8) Uani 1 1 d . . . H25 H 0.0793 -0.0965 0.4515 0.039 Uiso 1 1 calc R . . C26 C 0.0388(4) -0.0305(5) 0.28057(19) 0.0490(11) Uani 1 1 d . . . H26 H -0.0341 -0.0229 0.2818 0.059 Uiso 1 1 calc R . . C27 C 0.1085(4) 0.0692(5) 0.26117(17) 0.0441(10) Uani 1 1 d . . . H27 H 0.0896 0.1538 0.2472 0.053 Uiso 1 1 calc R . . C28 C 0.2118(3) 0.0178(4) 0.26663(16) 0.0398(9) Uani 1 1 d . . . H28 H 0.2730 0.0627 0.2571 0.048 Uiso 1 1 calc R . . C29 C 0.2058(4) -0.1142(4) 0.28916(17) 0.0409(9) Uani 1 1 d . . . H29 H 0.2625 -0.1713 0.2969 0.049 Uiso 1 1 calc R . . C30 C 0.0997(4) -0.1443(4) 0.29775(19) 0.0467(10) Uani 1 1 d . . . H30 H 0.0739 -0.2246 0.3122 0.056 Uiso 1 1 calc R . . C31 C -0.0515(3) 0.1189(3) 0.41671(17) 0.0313(8) Uani 1 1 d . . . C32 C -0.0368(3) 0.3629(3) 0.44041(18) 0.0332(8) Uani 1 1 d . . . H32A H 0.0340 0.3413 0.4556 0.040 Uiso 1 1 calc R . . H32B H -0.0716 0.4106 0.4722 0.040 Uiso 1 1 calc R . . C33 C -0.0303(3) 0.4530(4) 0.3856(2) 0.0438(10) Uani 1 1 d . . . H33A H -0.0006 0.4041 0.3524 0.053 Uiso 1 1 calc R . . H33B H -0.1004 0.4826 0.3724 0.053 Uiso 1 1 calc R . . C34 C -0.2114(3) 0.2473(4) 0.42769(19) 0.0399(9) Uani 1 1 d . . . H34A H -0.2383 0.1712 0.4494 0.048 Uiso 1 1 calc R . . H34B H -0.2322 0.3279 0.4484 0.048 Uiso 1 1 calc R . . C35 C -0.2560(3) 0.2481(4) 0.3643(2) 0.0428(9) Uani 1 1 d . . . H35A H -0.2237 0.3190 0.3416 0.051 Uiso 1 1 calc R . . H35B H -0.2408 0.1638 0.3449 0.051 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 0.0233(2) 0.0269(3) 0.0259(2) 0.00033(19) 0.00170(18) 0.00401(19) N1 0.0200(16) 0.0203(16) 0.148(4) 0.019(2) 0.012(2) 0.0031(13) O1 0.0274(14) 0.0187(12) 0.116(3) 0.0138(15) -0.0117(16) -0.0018(11) O2 0.058(2) 0.0327(16) 0.118(3) -0.0167(18) 0.043(2) -0.0179(15) C1 0.0260(17) 0.0239(16) 0.0329(17) 0.0002(13) -0.0044(13) 0.0060(13) C2 0.0249(17) 0.0303(18) 0.043(2) 0.0096(15) 0.0002(15) 0.0025(14) C3 0.0276(19) 0.059(3) 0.044(2) 0.024(2) 0.0111(16) 0.0102(18) C4 0.053(2) 0.057(3) 0.0275(18) 0.0109(18) 0.0121(17) 0.034(2) C5 0.054(2) 0.0310(19) 0.0283(17) -0.0040(15) -0.0091(16) 0.0159(17) C6 0.039(2) 0.066(3) 0.035(2) 0.004(2) 0.0140(17) 0.000(2) C7 0.052(2) 0.045(2) 0.0284(19) -0.0069(16) 0.0045(17) 0.0079(19) C8 0.042(2) 0.047(2) 0.0283(18) -0.0001(16) -0.0077(15) -0.0015(18) C9 0.049(2) 0.039(2) 0.0297(18) 0.0089(16) -0.0013(16) 0.0099(18) C10 0.054(3) 0.040(2) 0.035(2) 0.0062(17) 0.0042(18) -0.0105(19) C11 0.0265(18) 0.0185(16) 0.069(3) 0.0020(17) -0.0052(17) 0.0025(14) C12 0.0263(18) 0.0205(17) 0.076(3) 0.0115(18) -0.0044(18) 0.0001(14) C13 0.070(3) 0.024(2) 0.083(3) -0.002(2) 0.037(3) 0.004(2) C14A 0.033(5) 0.023(4) 0.041(5) 0.004(3) 0.003(4) 0.001(3) C15A 0.044(5) 0.020(3) 0.040(4) 0.002(3) 0.006(4) 0.005(3) O3A 0.028(3) 0.022(3) 0.094(5) -0.004(3) 0.001(3) 0.001(2) C14B 0.012(3) 0.018(3) 0.026(4) 0.002(2) -0.008(3) 0.000(2) C15B 0.025(4) 0.020(3) 0.034(4) 0.005(3) 0.009(3) 0.001(3) O3B 0.023(2) 0.015(2) 0.047(3) 0.007(2) 0.009(2) 0.0020(17) Fe2 0.0246(2) 0.0247(2) 0.0238(2) -0.00078(18) -0.00215(18) 0.00155(18) N2 0.0264(15) 0.0201(14) 0.062(2) -0.0044(14) -0.0010(14) 0.0020(12) O21 0.0287(13) 0.0183(12) 0.076(2) -0.0033(12) 0.0112(13) -0.0018(10) O22 0.0424(17) 0.0351(16) 0.101(3) 0.0144(17) -0.0179(17) -0.0150(13) O23 0.0342(15) 0.0307(14) 0.084(2) -0.0075(15) -0.0075(14) 0.0002(12) C21 0.0273(17) 0.0216(15) 0.0290(16) 0.0003(13) 0.0031(13) 0.0043(13) C22 0.0263(17) 0.0258(17) 0.0348(18) -0.0039(14) -0.0011(14) -0.0022(13) C23 0.0244(17) 0.043(2) 0.0362(19) -0.0122(16) -0.0047(14) -0.0008(15) C24 0.038(2) 0.046(2) 0.0250(16) -0.0057(15) -0.0071(14) 0.0189(17) C25 0.043(2) 0.0269(17) 0.0276(17) 0.0048(14) 0.0050(14) 0.0086(15) C26 0.040(2) 0.070(3) 0.036(2) -0.010(2) -0.0141(17) -0.002(2) C27 0.058(3) 0.046(2) 0.0270(18) 0.0012(16) -0.0079(18) 0.010(2) C28 0.047(2) 0.047(2) 0.0256(17) -0.0030(16) 0.0070(16) 0.0005(19) C29 0.055(3) 0.040(2) 0.0271(18) -0.0086(16) -0.0008(17) 0.0142(19) C30 0.062(3) 0.038(2) 0.040(2) -0.0101(18) -0.0068(19) -0.012(2) C31 0.0321(18) 0.0196(16) 0.042(2) 0.0009(14) 0.0054(15) 0.0024(14) C32 0.0290(18) 0.0202(16) 0.050(2) -0.0072(15) -0.0024(16) 0.0013(13) C33 0.046(2) 0.0240(18) 0.059(3) 0.0025(17) -0.015(2) -0.0018(16) C34 0.044(2) 0.0277(19) 0.047(2) -0.0048(16) -0.0013(18) 0.0041(16) C35 0.046(2) 0.032(2) 0.051(2) -0.0003(18) 0.0115(19) 0.0031(17) _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(4) . ? Fe1 C2 2.034(4) . ? Fe1 C6 2.036(4) . ? Fe1 C7 2.039(4) . ? Fe1 C1 2.043(3) . ? Fe1 C8 2.045(4) . ? Fe1 C10 2.045(4) . ? Fe1 C4 2.050(4) . ? Fe1 C3 2.051(4) . ? Fe1 C9 2.051(4) . ? N1 C11 1.346(5) . ? N1 C12 1.457(5) . ? N1 C14B 1.488(7) . ? N1 C14A 1.599(10) . ? O1 C11 1.236(5) . ? O2 C13 1.414(5) . ? O2 H91 0.9218 . ? C1 C2 1.435(5) . ? C1 C5 1.437(5) . ? C1 C11 1.483(5) . ? C2 C3 1.418(5) . ? C2 H2 0.9300 . ? C3 C4 1.410(7) . ? C3 H3 0.9300 . ? C4 C5 1.410(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.406(6) . ? C6 C10 1.418(6) . ? C6 H6 0.9300 . ? C7 C8 1.414(6) . ? C7 H7 0.9300 . ? C8 C9 1.420(6) . ? C8 H8 0.9300 . ? C9 C10 1.407(6) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C12 C13 1.510(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14A C15A 1.495(11) . ? C14A H14A 0.9700 . ? C14A H14B 0.9700 . ? C15A O3A 1.433(10) . ? C15A H15A 0.9700 . ? C15A H15B 0.9700 . ? O3A H92A 1.0111 . ? O3A H92B 1.0024 . ? C14B C15B 1.531(10) . ? C14B H14C 0.9700 . ? C14B H14D 0.9700 . ? C15B O3B 1.422(9) . ? C15B H15C 0.9700 . ? C15B H15D 0.9700 . ? O3B H92A 0.8845 . ? O3B H92B 0.8907 . ? Fe2 C25 2.034(3) . ? Fe2 C22 2.035(3) . ? Fe2 C26 2.037(4) . ? Fe2 C21 2.040(3) . ? Fe2 C30 2.043(4) . ? Fe2 C27 2.043(4) . ? Fe2 C29 2.045(4) . ? Fe2 C28 2.046(4) . ? Fe2 C23 2.049(3) . ? Fe2 C24 2.052(3) . ? N2 C31 1.349(4) . ? N2 C32 1.453(4) . ? N2 C34 1.496(5) . ? O21 C31 1.244(4) . ? O22 C33 1.415(5) . ? O22 H93 0.9161 . ? O23 C35 1.453(5) . ? O23 H94 1.0156 . ? C21 C22 1.431(5) . ? C21 C25 1.434(5) . ? C21 C31 1.486(5) . ? C22 C23 1.419(5) . ? C22 H22 0.9300 . ? C23 C24 1.401(6) . ? C23 H23 0.9300 . ? C24 C25 1.413(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.414(7) . ? C26 C30 1.420(6) . ? C26 H26 0.9300 . ? C27 C28 1.408(6) . ? C27 H27 0.9300 . ? C28 C29 1.416(6) . ? C28 H28 0.9300 . ? C29 C30 1.400(6) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C32 C33 1.513(6) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.481(6) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Fe1 C2 69.25(16) . . ? C5 Fe1 C6 120.30(18) . . ? C2 Fe1 C6 126.53(17) . . ? C5 Fe1 C7 154.55(17) . . ? C2 Fe1 C7 107.26(17) . . ? C6 Fe1 C7 40.38(18) . . ? C5 Fe1 C1 41.32(14) . . ? C2 Fe1 C1 41.22(14) . . ? C6 Fe1 C1 108.02(16) . . ? C7 Fe1 C1 119.38(15) . . ? C5 Fe1 C8 163.67(16) . . ? C2 Fe1 C8 118.60(16) . . ? C6 Fe1 C8 68.07(18) . . ? C7 Fe1 C8 40.51(16) . . ? C1 Fe1 C8 153.52(15) . . ? C5 Fe1 C10 108.27(17) . . ? C2 Fe1 C10 164.70(16) . . ? C6 Fe1 C10 40.67(18) . . ? C7 Fe1 C10 68.11(18) . . ? C1 Fe1 C10 127.10(16) . . ? C8 Fe1 C10 68.07(17) . . ? C5 Fe1 C4 40.44(17) . . ? C2 Fe1 C4 68.22(16) . . ? C6 Fe1 C4 154.9(2) . . ? C7 Fe1 C4 163.52(19) . . ? C1 Fe1 C4 68.43(14) . . ? C8 Fe1 C4 126.42(17) . . ? C10 Fe1 C4 120.34(18) . . ? C5 Fe1 C3 68.43(18) . . ? C2 Fe1 C3 40.62(15) . . ? C6 Fe1 C3 163.76(19) . . ? C7 Fe1 C3 126.22(19) . . ? C1 Fe1 C3 68.65(15) . . ? C8 Fe1 C3 107.40(17) . . ? C10 Fe1 C3 153.81(17) . . ? C4 Fe1 C3 40.22(19) . . ? C5 Fe1 C9 126.52(16) . . ? C2 Fe1 C9 153.28(16) . . ? C6 Fe1 C9 67.91(18) . . ? C7 Fe1 C9 68.00(17) . . ? C1 Fe1 C9 164.44(16) . . ? C8 Fe1 C9 40.57(16) . . ? C10 Fe1 C9 40.16(17) . . ? C4 Fe1 C9 108.46(16) . . ? C3 Fe1 C9 119.54(16) . . ? C11 N1 C12 128.0(3) . . ? C11 N1 C14B 115.9(4) . . ? C12 N1 C14B 112.6(4) . . ? C11 N1 C14A 113.9(4) . . ? C12 N1 C14A 116.2(4) . . ? C14B N1 C14A 36.0(4) . . ? C13 O2 H91 115.1 . . ? C2 C1 C5 107.0(3) . . ? C2 C1 C11 131.1(3) . . ? C5 C1 C11 121.7(3) . . ? C2 C1 Fe1 69.05(19) . . ? C5 C1 Fe1 68.82(19) . . ? C11 C1 Fe1 123.5(3) . . ? C3 C2 C1 108.0(3) . . ? C3 C2 Fe1 70.3(2) . . ? C1 C2 Fe1 69.74(19) . . ? C3 C2 H2 126.0 . . ? C1 C2 H2 126.0 . . ? Fe1 C2 H2 125.5 . . ? C4 C3 C2 108.1(4) . . ? C4 C3 Fe1 69.8(2) . . ? C2 C3 Fe1 69.0(2) . . ? C4 C3 H3 125.9 . . ? C2 C3 H3 125.9 . . ? Fe1 C3 H3 126.8 . . ? C5 C4 C3 108.9(3) . . ? C5 C4 Fe1 69.0(2) . . ? C3 C4 Fe1 69.9(2) . . ? C5 C4 H4 125.5 . . ? C3 C4 H4 125.5 . . ? Fe1 C4 H4 127.1 . . ? C4 C5 C1 107.9(4) . . ? C4 C5 Fe1 70.6(2) . . ? C1 C5 Fe1 69.9(2) . . ? C4 C5 H5 126.1 . . ? C1 C5 H5 126.1 . . ? Fe1 C5 H5 125.1 . . ? C7 C6 C10 108.2(4) . . ? C7 C6 Fe1 69.9(2) . . ? C10 C6 Fe1 70.0(2) . . ? C7 C6 H6 125.9 . . ? C10 C6 H6 125.9 . . ? Fe1 C6 H6 125.7 . . ? C6 C7 C8 108.2(4) . . ? C6 C7 Fe1 69.7(2) . . ? C8 C7 Fe1 70.0(2) . . ? C6 C7 H7 125.9 . . ? C8 C7 H7 125.9 . . ? Fe1 C7 H7 126.0 . . ? C7 C8 C9 107.6(4) . . ? C7 C8 Fe1 69.5(2) . . ? C9 C8 Fe1 69.9(2) . . ? C7 C8 H8 126.2 . . ? C9 C8 H8 126.2 . . ? Fe1 C8 H8 125.9 . . ? C10 C9 C8 108.2(4) . . ? C10 C9 Fe1 69.7(2) . . ? C8 C9 Fe1 69.5(2) . . ? C10 C9 H9 125.9 . . ? C8 C9 H9 125.9 . . ? Fe1 C9 H9 126.5 . . ? C9 C10 C6 107.8(4) . . ? C9 C10 Fe1 70.1(2) . . ? C6 C10 Fe1 69.3(2) . . ? C9 C10 H10 126.1 . . ? C6 C10 H10 126.1 . . ? Fe1 C10 H10 126.0 . . ? O1 C11 N1 120.4(3) . . ? O1 C11 C1 120.1(3) . . ? N1 C11 C1 119.5(3) . . ? N1 C12 C13 112.0(4) . . ? N1 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? N1 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? O2 C13 C12 109.2(4) . . ? O2 C13 H13A 109.8 . . ? C12 C13 H13A 109.8 . . ? O2 C13 H13B 109.8 . . ? C12 C13 H13B 109.8 . . ? H13A C13 H13B 108.3 . . ? C15A C14A N1 99.4(7) . . ? C15A C14A H14A 111.9 . . ? N1 C14A H14A 111.9 . . ? C15A C14A H14B 111.9 . . ? N1 C14A H14B 111.9 . . ? H14A C14A H14B 109.6 . . ? O3A C15A C14A 109.7(7) . . ? O3A C15A H15A 109.7 . . ? C14A C15A H15A 109.7 . . ? O3A C15A H15B 109.7 . . ? C14A C15A H15B 109.7 . . ? H15A C15A H15B 108.2 . . ? C15A O3A H92A 108.7 . . ? C15A O3A H92B 108.9 . . ? H92A O3A H92B 0.4 . . ? N1 C14B C15B 102.6(5) . . ? N1 C14B H14C 111.3 . . ? C15B C14B H14C 111.3 . . ? N1 C14B H14D 111.3 . . ? C15B C14B H14D 111.3 . . ? H14C C14B H14D 109.2 . . ? O3B C15B C14B 111.4(6) . . ? O3B C15B H15C 109.3 . . ? C14B C15B H15C 109.3 . . ? O3B C15B H15D 109.3 . . ? C14B C15B H15D 109.3 . . ? H15C C15B H15D 108.0 . . ? C15B O3B H92A 111.9 . . ? C15B O3B H92B 111.9 . . ? H92A O3B H92B 0.6 . . ? C25 Fe2 C22 68.83(14) . . ? C25 Fe2 C26 121.05(18) . . ? C22 Fe2 C26 126.49(17) . . ? C25 Fe2 C21 41.20(13) . . ? C22 Fe2 C21 41.12(13) . . ? C26 Fe2 C21 108.26(17) . . ? C25 Fe2 C30 108.65(17) . . ? C22 Fe2 C30 164.58(17) . . ? C26 Fe2 C30 40.71(19) . . ? C21 Fe2 C30 127.06(17) . . ? C25 Fe2 C27 155.57(17) . . ? C22 Fe2 C27 107.49(16) . . ? C26 Fe2 C27 40.53(18) . . ? C21 Fe2 C27 120.05(15) . . ? C30 Fe2 C27 68.13(18) . . ? C25 Fe2 C29 126.29(15) . . ? C22 Fe2 C29 153.61(16) . . ? C26 Fe2 C29 67.90(18) . . ? C21 Fe2 C29 164.06(16) . . ? C30 Fe2 C29 40.06(18) . . ? C27 Fe2 C29 67.86(16) . . ? C25 Fe2 C28 163.02(16) . . ? C22 Fe2 C28 119.01(16) . . ? C26 Fe2 C28 68.03(18) . . ? C21 Fe2 C28 154.08(15) . . ? C30 Fe2 C28 67.93(18) . . ? C27 Fe2 C28 40.29(17) . . ? C29 Fe2 C28 40.49(16) . . ? C25 Fe2 C23 68.04(16) . . ? C22 Fe2 C23 40.67(14) . . ? C26 Fe2 C23 163.53(19) . . ? C21 Fe2 C23 68.66(14) . . ? C30 Fe2 C23 153.86(17) . . ? C27 Fe2 C23 125.82(18) . . ? C29 Fe2 C23 119.51(16) . . ? C28 Fe2 C23 107.25(16) . . ? C25 Fe2 C24 40.46(15) . . ? C22 Fe2 C24 68.11(15) . . ? C26 Fe2 C24 155.51(19) . . ? C21 Fe2 C24 68.60(14) . . ? C30 Fe2 C24 120.54(17) . . ? C27 Fe2 C24 162.49(18) . . ? C29 Fe2 C24 108.07(15) . . ? C28 Fe2 C24 125.64(16) . . ? C23 Fe2 C24 39.97(16) . . ? C31 N2 C32 126.7(3) . . ? C31 N2 C34 116.9(3) . . ? C32 N2 C34 116.3(3) . . ? C33 O22 H93 110.7 . . ? C35 O23 H94 106.2 . . ? C22 C21 C25 106.8(3) . . ? C22 C21 C31 131.4(3) . . ? C25 C21 C31 121.8(3) . . ? C22 C21 Fe2 69.26(19) . . ? C25 C21 Fe2 69.20(19) . . ? C31 C21 Fe2 124.2(2) . . ? C23 C22 C21 108.0(3) . . ? C23 C22 Fe2 70.2(2) . . ? C21 C22 Fe2 69.62(19) . . ? C23 C22 H22 126.0 . . ? C21 C22 H22 126.0 . . ? Fe2 C22 H22 125.8 . . ? C24 C23 C22 108.5(3) . . ? C24 C23 Fe2 70.1(2) . . ? C22 C23 Fe2 69.15(19) . . ? C24 C23 H23 125.8 . . ? C22 C23 H23 125.8 . . ? Fe2 C23 H23 126.5 . . ? C23 C24 C25 108.5(3) . . ? C23 C24 Fe2 69.9(2) . . ? C25 C24 Fe2 69.1(2) . . ? C23 C24 H24 125.7 . . ? C25 C24 H24 125.7 . . ? Fe2 C24 H24 126.8 . . ? C24 C25 C21 108.2(3) . . ? C24 C25 Fe2 70.4(2) . . ? C21 C25 Fe2 69.60(19) . . ? C24 C25 H25 125.9 . . ? C21 C25 H25 125.9 . . ? Fe2 C25 H25 125.6 . . ? C27 C26 C30 107.8(4) . . ? C27 C26 Fe2 70.0(2) . . ? C30 C26 Fe2 69.9(2) . . ? C27 C26 H26 126.1 . . ? C30 C26 H26 126.1 . . ? Fe2 C26 H26 125.7 . . ? C28 C27 C26 108.1(4) . . ? C28 C27 Fe2 69.9(2) . . ? C26 C27 Fe2 69.5(2) . . ? C28 C27 H27 126.0 . . ? C26 C27 H27 126.0 . . ? Fe2 C27 H27 126.2 . . ? C27 C28 C29 107.8(4) . . ? C27 C28 Fe2 69.8(2) . . ? C29 C28 Fe2 69.7(2) . . ? C27 C28 H28 126.1 . . ? C29 C28 H28 126.1 . . ? Fe2 C28 H28 126.0 . . ? C30 C29 C28 108.4(4) . . ? C30 C29 Fe2 69.9(2) . . ? C28 C29 Fe2 69.8(2) . . ? C30 C29 H29 125.8 . . ? C28 C29 H29 125.8 . . ? Fe2 C29 H29 126.1 . . ? C29 C30 C26 107.9(4) . . ? C29 C30 Fe2 70.0(2) . . ? C26 C30 Fe2 69.4(2) . . ? C29 C30 H30 126.1 . . ? C26 C30 H30 126.1 . . ? Fe2 C30 H30 126.1 . . ? O21 C31 N2 119.8(3) . . ? O21 C31 C21 119.6(3) . . ? N2 C31 C21 120.5(3) . . ? N2 C32 C33 113.0(3) . . ? N2 C32 H32A 109.0 . . ? C33 C32 H32A 109.0 . . ? N2 C32 H32B 109.0 . . ? C33 C32 H32B 109.0 . . ? H32A C32 H32B 107.8 . . ? O22 C33 C32 110.0(3) . . ? O22 C33 H33A 109.7 . . ? C32 C33 H33A 109.7 . . ? O22 C33 H33B 109.7 . . ? C32 C33 H33B 109.7 . . ? H33A C33 H33B 108.2 . . ? C35 C34 N2 109.3(3) . . ? C35 C34 H34A 109.8 . . ? N2 C34 H34A 109.8 . . ? C35 C34 H34B 109.8 . . ? N2 C34 H34B 109.8 . . ? H34A C34 H34B 108.3 . . ? O23 C35 C34 109.9(3) . . ? O23 C35 H35A 109.7 . . ? C34 C35 H35A 109.7 . . ? O23 C35 H35B 109.7 . . ? C34 C35 H35B 109.7 . . ? H35A C35 H35B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.647 _refine_diff_density_min -0.613 _refine_diff_density_rms 0.086 data_ps1064 _database_code_depnum_ccdc_archive 'CCDC 254371' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N',N'-tetrakis(2-hydroxyethyl)-1,1'-ferrocenedicarboxamide ; _chemical_name_common N,N,N',N'-tetrakis(2-hydroxyethyl)-1,1'-ferrocenedicarboxamide _chemical_formula_moiety 'C20 H28 Fe N2 O6' _chemical_formula_sum 'C20 H28 Fe N2 O6' _chemical_formula_weight 448.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.3500(3) _cell_length_b 7.7500(4) _cell_length_c 15.5960(5) _cell_angle_alpha 90.00 _cell_angle_beta 130.317(2) _cell_angle_gamma 90.00 _cell_volume 1967.6(1) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4289 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.807 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\w and \p scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_reflns_number 18339 _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2261 _reflns_number_gt 1791 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material ? _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^)+(0.0295P)^2^+2.2617P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2261 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0785 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Fe Fe 0.0000 0.35140(5) 0.2500 0.01639(12) Uani 1 2 d S . . O1 O -0.02786(8) -0.07467(17) 0.35381(12) 0.0243(3) Uani 1 1 d . . . O2 O 0.18183(9) 0.1360(2) 0.73177(12) 0.0256(3) Uani 1 1 d . . . H91 H 0.1403(17) 0.105(4) 0.715(2) 0.049(9) Uiso 1 1 d . . . O3 O 0.18869(9) -0.39777(19) 0.54148(14) 0.0290(4) Uani 1 1 d . . . H92 H 0.2265(18) -0.381(4) 0.608(3) 0.061(10) Uiso 1 1 d . . . N N 0.09563(9) 0.0346(2) 0.49660(13) 0.0192(4) Uani 1 1 d . . . C1 C -0.01833(11) 0.2249(2) 0.34623(16) 0.0177(4) Uani 1 1 d . . . C2 C -0.09328(11) 0.2321(3) 0.23158(16) 0.0193(4) Uani 1 1 d . . . H2 H -0.1234 0.1374 0.1862 0.023 Uiso 1 1 calc R . . C3 C -0.11377(12) 0.4077(3) 0.19899(18) 0.0217(4) Uani 1 1 d . . . H3 H -0.1592 0.4479 0.1287 0.026 Uiso 1 1 calc R . . C4 C -0.05280(12) 0.5105(3) 0.29238(17) 0.0218(4) Uani 1 1 d . . . H4 H -0.0515 0.6305 0.2939 0.026 Uiso 1 1 calc R . . C5 C 0.00596(12) 0.4009(2) 0.38311(17) 0.0196(4) Uani 1 1 d . . . H5 H 0.0523 0.4364 0.4543 0.023 Uiso 1 1 calc R . . C6 C 0.01735(11) 0.0544(2) 0.40055(16) 0.0184(4) Uani 1 1 d . . . C7 C 0.12351(12) -0.1418(3) 0.54121(17) 0.0220(4) Uani 1 1 d . . . H7A H 0.0780 -0.2073 0.5244 0.026 Uiso 1 1 calc R . . H7B H 0.1664 -0.1367 0.6223 0.026 Uiso 1 1 calc R . . C8 C 0.15613(12) -0.2329(3) 0.49114(18) 0.0249(5) Uani 1 1 d . . . H8A H 0.1121 -0.2467 0.4108 0.030 Uiso 1 1 calc R . . H8B H 0.1988 -0.1632 0.5027 0.030 Uiso 1 1 calc R . . C9 C 0.15826(11) 0.1703(3) 0.55661(17) 0.0213(4) Uani 1 1 d . . . H9A H 0.1458 0.2577 0.5030 0.026 Uiso 1 1 calc R . . H9B H 0.2112 0.1207 0.5890 0.026 Uiso 1 1 calc R . . C10 C 0.16458(12) 0.2559(3) 0.64938(17) 0.0246(5) Uani 1 1 d . . . H10A H 0.2077 0.3422 0.6859 0.029 Uiso 1 1 calc R . . H10B H 0.1133 0.3145 0.6164 0.029 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 Fe 0.0166(2) 0.0154(2) 0.0175(2) 0.000 0.01113(17) 0.000 O1 0.0222(7) 0.0163(7) 0.0279(8) 0.0000(6) 0.0134(6) -0.0031(6) O2 0.0203(8) 0.0307(9) 0.0176(7) 0.0037(6) 0.0085(6) -0.0021(7) O3 0.0274(8) 0.0214(8) 0.0227(8) -0.0013(6) 0.0091(7) 0.0045(6) N 0.0192(8) 0.0167(8) 0.0185(8) 0.0013(7) 0.0108(7) 0.0008(6) C1 0.0179(9) 0.0185(10) 0.0200(10) 0.0013(8) 0.0137(8) 0.0006(8) C2 0.0159(9) 0.0217(10) 0.0204(10) -0.0004(8) 0.0118(8) -0.0034(8) C3 0.0162(9) 0.0260(11) 0.0250(11) 0.0053(9) 0.0143(9) 0.0048(8) C4 0.0262(10) 0.0181(10) 0.0273(11) 0.0019(8) 0.0201(9) 0.0042(8) C5 0.0252(10) 0.0176(10) 0.0194(10) -0.0022(8) 0.0160(9) -0.0006(8) C6 0.0211(10) 0.0169(10) 0.0227(10) -0.0012(8) 0.0166(9) -0.0014(8) C7 0.0216(10) 0.0193(10) 0.0189(10) 0.0035(9) 0.0104(8) 0.0042(8) C8 0.0248(11) 0.0215(11) 0.0244(11) 0.0026(9) 0.0141(9) 0.0047(9) C9 0.0157(9) 0.0232(11) 0.0207(10) -0.0003(8) 0.0099(8) -0.0015(8) C10 0.0238(10) 0.0220(11) 0.0189(10) 0.0003(8) 0.0097(9) -0.0031(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe C1 2.0315(19) . ? Fe C1 2.0315(19) 2 ? Fe C5 2.033(2) . ? Fe C5 2.033(2) 2 ? Fe C2 2.0405(19) . ? Fe C2 2.0405(19) 2 ? Fe C4 2.048(2) 2 ? Fe C4 2.048(2) . ? Fe C3 2.0549(19) 2 ? Fe C3 2.0549(19) . ? O1 C6 1.246(2) . ? O2 C10 1.428(2) . ? O2 H91 0.78(3) . ? O3 C8 1.423(2) . ? O3 H92 0.81(3) . ? N C6 1.349(2) . ? N C9 1.467(2) . ? N C7 1.473(2) . ? C1 C2 1.435(3) . ? C1 C5 1.441(3) . ? C1 C6 1.486(3) . ? C2 C3 1.419(3) . ? C2 H2 0.9300 . ? C3 C4 1.413(3) . ? C3 H3 0.9300 . ? C4 C5 1.414(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.516(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.516(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Fe C1 122.27(11) . 2 ? C1 Fe C5 41.53(8) . . ? C1 Fe C5 158.59(8) 2 . ? C1 Fe C5 158.59(8) . 2 ? C1 Fe C5 41.53(8) 2 2 ? C5 Fe C5 158.22(11) . 2 ? C1 Fe C2 41.26(7) . . ? C1 Fe C2 108.32(8) 2 . ? C5 Fe C2 68.89(8) . . ? C5 Fe C2 122.10(8) 2 . ? C1 Fe C2 108.32(8) . 2 ? C1 Fe C2 41.26(7) 2 2 ? C5 Fe C2 122.10(8) . 2 ? C5 Fe C2 68.89(8) 2 2 ? C2 Fe C2 126.11(11) . 2 ? C1 Fe C4 159.82(8) . 2 ? C1 Fe C4 69.07(8) 2 2 ? C5 Fe C4 122.16(8) . 2 ? C5 Fe C4 40.56(8) 2 2 ? C2 Fe C4 156.71(8) . 2 ? C2 Fe C4 68.11(8) 2 2 ? C1 Fe C4 69.07(8) . . ? C1 Fe C4 159.82(8) 2 . ? C5 Fe C4 40.56(8) . . ? C5 Fe C4 122.16(8) 2 . ? C2 Fe C4 68.11(8) . . ? C2 Fe C4 156.71(8) 2 . ? C4 Fe C4 105.94(12) 2 . ? C1 Fe C3 124.12(8) . 2 ? C1 Fe C3 69.14(8) 2 2 ? C5 Fe C3 106.70(8) . 2 ? C5 Fe C3 68.44(8) 2 2 ? C2 Fe C3 162.22(8) . 2 ? C2 Fe C3 40.54(8) 2 2 ? C4 Fe C3 40.30(8) 2 2 ? C4 Fe C3 120.47(8) . 2 ? C1 Fe C3 69.14(8) . . ? C1 Fe C3 124.12(8) 2 . ? C5 Fe C3 68.44(8) . . ? C5 Fe C3 106.70(8) 2 . ? C2 Fe C3 40.54(8) . . ? C2 Fe C3 162.22(8) 2 . ? C4 Fe C3 120.47(8) 2 . ? C4 Fe C3 40.30(8) . . ? C3 Fe C3 155.50(12) 2 . ? C10 O2 H91 109(2) . . ? C8 O3 H92 107(2) . . ? C6 N C9 126.14(16) . . ? C6 N C7 117.50(16) . . ? C9 N C7 116.16(15) . . ? C2 C1 C5 106.48(17) . . ? C2 C1 C6 119.49(17) . . ? C5 C1 C6 134.03(17) . . ? C2 C1 Fe 69.71(11) . . ? C5 C1 Fe 69.27(11) . . ? C6 C1 Fe 125.28(13) . . ? C3 C2 C1 108.70(17) . . ? C3 C2 Fe 70.27(11) . . ? C1 C2 Fe 69.04(10) . . ? C3 C2 H2 125.7 . . ? C1 C2 H2 125.7 . . ? Fe C2 H2 126.6 . . ? C4 C3 C2 107.86(17) . . ? C4 C3 Fe 69.57(11) . . ? C2 C3 Fe 69.18(10) . . ? C4 C3 H3 126.1 . . ? C2 C3 H3 126.1 . . ? Fe C3 H3 126.7 . . ? C3 C4 C5 108.77(17) . . ? C3 C4 Fe 70.12(11) . . ? C5 C4 Fe 69.15(11) . . ? C3 C4 H4 125.6 . . ? C5 C4 H4 125.6 . . ? Fe C4 H4 126.7 . . ? C4 C5 C1 108.18(17) . . ? C4 C5 Fe 70.29(12) . . ? C1 C5 Fe 69.20(11) . . ? C4 C5 H5 125.9 . . ? C1 C5 H5 125.9 . . ? Fe C5 H5 126.2 . . ? O1 C6 N 119.48(18) . . ? O1 C6 C1 117.56(16) . . ? N C6 C1 122.96(17) . . ? N C7 C8 111.66(17) . . ? N C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? O3 C8 C7 110.94(17) . . ? O3 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.0 . . ? N C9 C10 113.85(16) . . ? N C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? N C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? O2 C10 C9 112.69(17) . . ? O2 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? O2 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.328 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.069