# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_ch14 _database_code_CSD 168911 # _audit_creation_method SHELXL-97 _journal_coden_Cambridge 440 loop_ _publ_author_name _publ_author_address 'Christian G. Hartinger' ; Institut fuer Anorganische Chemie der Universitaet Wien Waehringer Strasse 42 A-1090 Vienna Austria ; 'Alexey A. Nazarov' ; Institut fuer Anorganische Chemie der Universitaet Wien Waehringer Strasse 42 A-1090 Vienna Austria ; 'Vladimir B. Arion' ; Institut fuer Anorganische Chemie der Universitaet Wien Waehringer Strasse 42 A-1090 Vienna Austria ; 'Gerald Giester' ; Institut of Mineralogy and Crystallography of the Universiy of Vienna Althanstrasse 14 A-1090 Vienna Austria ; 'Michael Jakupec' ; Institut fuer Anorganische Chemie der Universitaet Wien Waehringer Strasse 42 A-1090 Vienna Austria ; 'Mathea S. Galanski' ; Institut fuer Anorganische Chemie der Universitaet Wien Waehringer Strasse 42 A-1090 Vienna Austria ; 'Bernhard K. Keppler' ; Institut fuer Anorganische Chemie der Universitaet Wien Waehringer Strasse 42 A-1090 Vienna Austria ; _publ_contact_author_name 'Prof Bernhard K. Keppler' _publ_contact_author_address ; Institute of Inorganic Chemistry University Vienna Waehringerstr. 42 Vienna A-1090 AUSTRIA ; _publ_contact_author_email 'BERNHARD.KEPPLER@UNIVIE.AC.AT' _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Novel glucose-ferrocenyl derivatives: synthesis and properties ; _chemical_name_systematic ; 2,3-{(R,S)-(ferrocene-1,1'-dicarbonyl)}-O-methyl-alpha-D-glucopyranoside ; _chemical_formula_moiety 'C19 H20 Fe O8 . H2O' _chemical_formula_sum 'C19 H22 Fe O9' _chemical_formula_weight 450.22 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' '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.8080(10) _cell_length_b 10.750(2) _cell_length_c 14.772(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.44(3) _cell_angle_gamma 90.00 _cell_volume 920.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.872 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4543 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4543 _reflns_number_gt 4268 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+0.3399P] 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 SHELXL _refine_ls_extinction_coef 0.0075(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.001(10) _refine_ls_number_reflns 4543 _refine_ls_number_parameters 274 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0272 _refine_ls_wR_factor_ref 0.0635 _refine_ls_wR_factor_gt 0.0622 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.077 _refine_ls_shift/su_mean 0.002 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.19795(4) 0.49771(3) 0.097318(16) 0.01304(7) Uani 1 d . . . O1 O 0.4895(2) 0.80714(14) 0.11618(10) 0.0219(3) Uani 1 d . . . O2 O 0.1416(2) 0.82080(12) 0.17778(9) 0.0151(3) Uani 1 d . . . O3 O 0.2586(2) 1.03903(12) 0.36575(9) 0.0153(3) Uani 1 d . . . O4 O -0.09197(19) 0.98645(15) 0.28724(8) 0.0174(3) Uani 1 d . . . O5 O 0.6087(2) 1.01819(13) 0.50684(9) 0.0203(3) Uani 1 d . . . H50 H 0.6749 1.0667 0.5424 0.030 Uiso 1 calc R . . O6 O 0.2316(2) 0.75305(12) 0.49962(9) 0.0186(3) Uani 1 d . . . H6 H 0.2805 0.6819 0.4953 0.028 Uiso 1 calc R . . O7 O 0.2857(2) 0.66202(12) 0.31116(9) 0.0144(3) Uani 1 d . . . O8 O -0.0662(2) 0.57073(13) 0.31266(10) 0.0220(3) Uani 1 d . . . C1 C 0.1805(3) 0.67956(18) 0.05938(12) 0.0142(4) Uani 1 d . . . C2 C -0.0475(3) 0.62858(18) 0.06449(13) 0.0155(4) Uani 1 d . . . H2 H -0.1599 0.6558 0.1022 0.019 Uiso 1 calc R . . C3 C -0.0692(3) 0.52888(16) 0.00132(12) 0.0167(4) Uani 1 d . . . H3 H -0.2000 0.4801 -0.0099 0.020 Uiso 1 calc R . . C4 C 0.1424(3) 0.51597(19) -0.04200(12) 0.0172(4) Uani 1 d . . . H4 H 0.1740 0.4571 -0.0857 0.021 Uiso 1 calc R . . C5 C 0.2968(3) 0.60910(17) -0.00641(13) 0.0163(4) Uani 1 d . . . H5 H 0.4469 0.6220 -0.0230 0.020 Uiso 1 calc R . . C6 C 0.2910(3) 0.77399(17) 0.11889(12) 0.0145(4) Uani 1 d . . . C7 C 0.2447(3) 0.87084(17) 0.26120(12) 0.0140(4) Uani 1 d . . . H7 H 0.4122 0.8770 0.2574 0.017 Uiso 1 calc R . . C8 C 0.1462(3) 0.9975(2) 0.28273(10) 0.0144(3) Uani 1 d . . . H8 H 0.1793 1.0558 0.2342 0.017 Uiso 1 calc R . . C9 C 0.2276(3) 0.95872(17) 0.44328(12) 0.0152(4) Uani 1 d . . . H9 H 0.0643 0.9590 0.4566 0.018 Uiso 1 calc R . . C10 C 0.3012(3) 0.82535(17) 0.42509(13) 0.0150(4) Uani 1 d . . . H10 H 0.4693 0.8217 0.4227 0.018 Uiso 1 calc R . . C11 C 0.1892(3) 0.78085(17) 0.33606(13) 0.0142(4) Uani 1 d . . . H11 H 0.0219 0.7739 0.3401 0.017 Uiso 1 calc R . . C12 C -0.2109(3) 1.10275(18) 0.28443(14) 0.0205(4) Uani 1 d . . . H12A H -0.1284 1.1613 0.3233 0.031 Uiso 1 calc R . . H12B H -0.3634 1.0914 0.3047 0.031 Uiso 1 calc R . . H12C H -0.2207 1.1338 0.2234 0.031 Uiso 1 calc R . . C13 C 0.3677(3) 1.0148(2) 0.52318(12) 0.0182(4) Uani 1 d . . . H13A H 0.3137 1.0986 0.5339 0.022 Uiso 1 calc R . . H13B H 0.3454 0.9659 0.5771 0.022 Uiso 1 calc R . . C14 C 0.1301(3) 0.57057(17) 0.29018(12) 0.0147(4) Uani 1 d . . . C15 C 0.2289(3) 0.47364(15) 0.23429(12) 0.0134(4) Uani 1 d . . . C16 C 0.0949(3) 0.37511(17) 0.19301(12) 0.0169(4) Uani 1 d . . . H16 H -0.0571 0.3558 0.2039 0.020 Uiso 1 calc R . . C17 C 0.2353(4) 0.31189(19) 0.13229(13) 0.0189(4) Uani 1 d . . . H17 H 0.1916 0.2433 0.0969 0.023 Uiso 1 calc R . . C18 C 0.4542(3) 0.37151(18) 0.13486(13) 0.0183(4) Uani 1 d . . . H18 H 0.5777 0.3487 0.1012 0.022 Uiso 1 calc R . . C19 C 0.4528(3) 0.47201(16) 0.19761(12) 0.0163(4) Uani 1 d . . . H19 H 0.5740 0.5264 0.2122 0.020 Uiso 1 calc R . . O9 O 0.8113(3) 0.80752(15) 0.57304(12) 0.0275(3) Uani 1 d . . . H91 H 0.930(5) 0.792(3) 0.5539(18) 0.034(8) Uiso 1 d . . . H92 H 0.758(6) 0.732(3) 0.593(2) 0.055(10) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01318(11) 0.01242(11) 0.01347(11) -0.00013(11) 0.00051(8) 0.00030(11) O1 0.0191(7) 0.0224(7) 0.0249(7) -0.0040(6) 0.0073(6) -0.0068(6) O2 0.0140(6) 0.0166(6) 0.0146(6) -0.0021(5) 0.0003(5) 0.0010(5) O3 0.0181(6) 0.0124(6) 0.0154(6) -0.0010(5) 0.0017(5) -0.0016(5) O4 0.0138(5) 0.0148(6) 0.0235(6) -0.0009(6) 0.0011(5) 0.0015(6) O5 0.0190(6) 0.0185(9) 0.0233(7) -0.0042(6) 0.0003(5) -0.0031(6) O6 0.0277(7) 0.0129(7) 0.0156(6) 0.0017(5) 0.0045(5) 0.0030(6) O7 0.0146(6) 0.0106(6) 0.0180(6) -0.0026(5) 0.0003(5) -0.0001(5) O8 0.0184(7) 0.0220(7) 0.0266(7) -0.0037(6) 0.0089(6) -0.0049(6) C1 0.0159(9) 0.0140(9) 0.0127(9) 0.0030(7) 0.0017(7) 0.0015(7) C2 0.0144(9) 0.0160(9) 0.0162(9) 0.0015(7) 0.0012(7) 0.0018(7) C3 0.0157(9) 0.0168(10) 0.0171(9) -0.0005(7) -0.0030(7) -0.0012(7) C4 0.0201(8) 0.0195(12) 0.0118(8) 0.0000(7) -0.0003(6) 0.0022(8) C5 0.0166(9) 0.0165(9) 0.0160(9) 0.0019(7) 0.0030(7) 0.0017(7) C6 0.0184(9) 0.0121(8) 0.0134(8) 0.0044(7) 0.0034(7) 0.0008(7) C7 0.0139(8) 0.0143(9) 0.0137(8) -0.0024(7) 0.0004(7) -0.0010(7) C8 0.0146(7) 0.0140(7) 0.0148(7) 0.0011(9) 0.0015(6) -0.0022(9) C9 0.0158(8) 0.0144(8) 0.0157(9) 0.0000(6) 0.0036(7) 0.0000(7) C10 0.0149(9) 0.0137(9) 0.0165(9) 0.0015(7) 0.0020(7) 0.0003(7) C11 0.0139(8) 0.0106(8) 0.0181(9) -0.0017(7) 0.0012(7) 0.0028(7) C12 0.0176(10) 0.0171(9) 0.0267(10) -0.0007(8) 0.0011(8) 0.0031(8) C13 0.0204(9) 0.0165(11) 0.0178(8) -0.0029(8) 0.0033(7) 0.0001(8) C14 0.0192(9) 0.0118(9) 0.0131(8) 0.0008(7) 0.0011(7) -0.0019(7) C15 0.0164(8) 0.0102(10) 0.0135(8) 0.0026(6) -0.0003(6) 0.0001(7) C16 0.0216(10) 0.0129(8) 0.0160(9) 0.0023(7) -0.0004(7) -0.0015(8) C17 0.0236(10) 0.0131(9) 0.0195(10) -0.0002(8) -0.0034(8) 0.0015(8) C18 0.0189(9) 0.0169(9) 0.0191(9) 0.0014(8) 0.0014(7) 0.0052(8) C19 0.0141(8) 0.0171(11) 0.0172(8) 0.0016(7) -0.0026(7) 0.0002(7) O9 0.0227(8) 0.0222(8) 0.0382(9) 0.0060(7) 0.0074(7) 0.0005(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C1 2.0344(19) . ? Fe1 C15 2.0371(18) . ? Fe1 C2 2.0406(19) . ? Fe1 C16 2.0482(19) . ? Fe1 C19 2.0493(19) . ? Fe1 C5 2.0535(19) . ? Fe1 C18 2.0650(19) . ? Fe1 C3 2.0658(19) . ? Fe1 C17 2.071(2) . ? Fe1 C4 2.0732(18) . ? O1 C6 1.209(2) . ? O2 C6 1.361(2) . ? O2 C7 1.441(2) . ? O3 C8 1.426(2) . ? O3 C9 1.454(2) . ? O4 C8 1.3938(19) . ? O4 C12 1.428(2) . ? O5 C13 1.435(2) . ? O5 H5 0.8200 . ? O6 C10 1.426(2) . ? O6 H6 0.8200 . ? O7 C14 1.358(2) . ? O7 C11 1.451(2) . ? O8 C14 1.206(2) . ? C1 C5 1.433(3) . ? C1 C2 1.439(3) . ? C1 C6 1.466(3) . ? C2 C3 1.422(3) . ? C2 H2 0.9300 . ? C3 C4 1.426(3) . ? C3 H3 0.9300 . ? C4 C5 1.423(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.518(3) . ? C7 C11 1.518(3) . ? C7 H7 0.9800 . ? C8 H8 0.9800 . ? C9 C13 1.518(3) . ? C9 C10 1.525(3) . ? C9 H9 0.9800 . ? C10 C11 1.510(3) . ? C10 H10 0.9800 . ? C11 H11 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.468(2) . ? C15 C16 1.429(3) . ? C15 C19 1.439(3) . ? C16 C17 1.421(3) . ? C16 H16 0.9300 . ? C17 C18 1.422(3) . ? C17 H17 0.9300 . ? C18 C19 1.424(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? O9 H91 0.78(3) . ? O9 H92 0.93(4) . ? 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 Fe1 C15 113.30(7) . . ? C1 Fe1 C2 41.36(7) . . ? C15 Fe1 C2 110.03(8) . . ? C1 Fe1 C16 142.80(8) . . ? C15 Fe1 C16 40.96(7) . . ? C2 Fe1 C16 112.25(8) . . ? C1 Fe1 C19 110.53(7) . . ? C15 Fe1 C19 41.22(7) . . ? C2 Fe1 C19 136.79(8) . . ? C16 Fe1 C19 69.06(7) . . ? C1 Fe1 C5 41.04(7) . . ? C15 Fe1 C5 143.44(7) . . ? C2 Fe1 C5 69.10(8) . . ? C16 Fe1 C5 175.26(8) . . ? C19 Fe1 C5 113.32(8) . . ? C1 Fe1 C18 136.76(8) . . ? C15 Fe1 C18 68.32(8) . . ? C2 Fe1 C18 177.18(8) . . ? C16 Fe1 C18 68.15(8) . . ? C19 Fe1 C18 40.49(7) . . ? C5 Fe1 C18 110.75(8) . . ? C1 Fe1 C3 68.41(7) . . ? C15 Fe1 C3 136.09(8) . . ? C2 Fe1 C3 40.51(7) . . ? C16 Fe1 C3 109.85(8) . . ? C19 Fe1 C3 176.84(8) . . ? C5 Fe1 C3 67.99(8) . . ? C18 Fe1 C3 142.24(8) . . ? C1 Fe1 C17 176.44(8) . . ? C15 Fe1 C17 68.17(7) . . ? C2 Fe1 C17 141.75(8) . . ? C16 Fe1 C17 40.35(8) . . ? C19 Fe1 C17 68.25(7) . . ? C5 Fe1 C17 135.95(8) . . ? C18 Fe1 C17 40.22(8) . . ? C3 Fe1 C17 113.00(8) . . ? C1 Fe1 C4 68.49(8) . . ? C15 Fe1 C4 175.73(8) . . ? C2 Fe1 C4 68.53(8) . . ? C16 Fe1 C4 135.36(8) . . ? C19 Fe1 C4 142.46(7) . . ? C5 Fe1 C4 40.35(8) . . ? C18 Fe1 C4 113.29(8) . . ? C3 Fe1 C4 40.32(7) . . ? C17 Fe1 C4 110.28(8) . . ? C6 O2 C7 115.87(14) . . ? C8 O3 C9 114.78(14) . . ? C8 O4 C12 113.83(16) . . ? C13 O5 H5 109.5 . . ? C10 O6 H6 109.5 . . ? C14 O7 C11 115.68(14) . . ? C5 C1 C2 107.88(16) . . ? C5 C1 C6 124.43(16) . . ? C2 C1 C6 127.14(17) . . ? C5 C1 Fe1 70.20(11) . . ? C2 C1 Fe1 69.55(11) . . ? C6 C1 Fe1 119.18(13) . . ? C3 C2 C1 107.36(17) . . ? C3 C2 Fe1 70.70(11) . . ? C1 C2 Fe1 69.09(11) . . ? C3 C2 H2 126.3 . . ? C1 C2 H2 126.3 . . ? Fe1 C2 H2 125.5 . . ? C2 C3 C4 108.83(17) . . ? C2 C3 Fe1 68.79(10) . . ? C4 C3 Fe1 70.12(10) . . ? C2 C3 H3 125.6 . . ? C4 C3 H3 125.6 . . ? Fe1 C3 H3 127.1 . . ? C5 C4 C3 107.85(16) . . ? C5 C4 Fe1 69.08(10) . . ? C3 C4 Fe1 69.56(10) . . ? C5 C4 H4 126.1 . . ? C3 C4 H4 126.1 . . ? Fe1 C4 H4 126.8 . . ? C4 C5 C1 108.07(16) . . ? C4 C5 Fe1 70.57(11) . . ? C1 C5 Fe1 68.77(11) . . ? C4 C5 H5 126.0 . . ? C1 C5 H5 126.0 . . ? Fe1 C5 H5 126.3 . . ? O1 C6 O2 123.88(17) . . ? O1 C6 C1 124.64(17) . . ? O2 C6 C1 111.48(15) . . ? O2 C7 C8 111.81(14) . . ? O2 C7 C11 106.82(14) . . ? C8 C7 C11 108.64(15) . . ? O2 C7 H7 109.8 . . ? C8 C7 H7 109.8 . . ? C11 C7 H7 109.8 . . ? O4 C8 O3 112.96(13) . . ? O4 C8 C7 108.76(17) . . ? O3 C8 C7 107.59(14) . . ? O4 C8 H8 109.2 . . ? O3 C8 H8 109.2 . . ? C7 C8 H8 109.2 . . ? O3 C9 C13 106.89(15) . . ? O3 C9 C10 111.73(14) . . ? C13 C9 C10 111.56(16) . . ? O3 C9 H9 108.9 . . ? C13 C9 H9 108.9 . . ? C10 C9 H9 108.9 . . ? O6 C10 C11 111.89(15) . . ? O6 C10 C9 106.33(14) . . ? C11 C10 C9 109.93(15) . . ? O6 C10 H10 109.5 . . ? C11 C10 H10 109.5 . . ? C9 C10 H10 109.5 . . ? O7 C11 C10 110.31(14) . . ? O7 C11 C7 105.92(14) . . ? C10 C11 C7 109.48(15) . . ? O7 C11 H11 110.3 . . ? C10 C11 H11 110.3 . . ? C7 C11 H11 110.3 . . ? O4 C12 H12A 109.5 . . ? O4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 C13 C9 111.24(15) . . ? O5 C13 H13A 109.4 . . ? C9 C13 H13A 109.4 . . ? O5 C13 H13B 109.4 . . ? C9 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? O8 C14 O7 124.25(17) . . ? O8 C14 C15 124.32(17) . . ? O7 C14 C15 111.40(15) . . ? C16 C15 C19 108.18(15) . . ? C16 C15 C14 123.00(16) . . ? C19 C15 C14 127.84(16) . . ? C16 C15 Fe1 69.94(10) . . ? C19 C15 Fe1 69.85(10) . . ? C14 C15 Fe1 117.02(12) . . ? C17 C16 C15 107.76(17) . . ? C17 C16 Fe1 70.70(11) . . ? C15 C16 Fe1 69.10(10) . . ? C17 C16 H16 126.1 . . ? C15 C16 H16 126.1 . . ? Fe1 C16 H16 125.7 . . ? C16 C17 C18 108.28(18) . . ? C16 C17 Fe1 68.95(11) . . ? C18 C17 Fe1 69.65(12) . . ? C16 C17 H17 125.9 . . ? C18 C17 H17 125.9 . . ? Fe1 C17 H17 127.1 . . ? C17 C18 C19 108.62(17) . . ? C17 C18 Fe1 70.13(11) . . ? C19 C18 Fe1 69.16(10) . . ? C17 C18 H18 125.7 . . ? C19 C18 H18 125.7 . . ? Fe1 C18 H18 126.6 . . ? C18 C19 C15 107.16(16) . . ? C18 C19 Fe1 70.35(10) . . ? C15 C19 Fe1 68.93(10) . . ? C18 C19 H19 126.4 . . ? C15 C19 H19 126.4 . . ? Fe1 C19 H19 125.9 . . ? H91 O9 H92 104(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 Fe1 C1 C5 146.84(11) . . . . ? C2 Fe1 C1 C5 -118.85(15) . . . . ? C16 Fe1 C1 C5 -175.58(13) . . . . ? C19 Fe1 C1 C5 102.34(12) . . . . ? C18 Fe1 C1 C5 64.27(15) . . . . ? C3 Fe1 C1 C5 -80.84(12) . . . . ? C17 Fe1 C1 C5 33.1(13) . . . . ? C4 Fe1 C1 C5 -37.35(11) . . . . ? C15 Fe1 C1 C2 -94.30(12) . . . . ? C16 Fe1 C1 C2 -56.73(17) . . . . ? C19 Fe1 C1 C2 -138.81(11) . . . . ? C5 Fe1 C1 C2 118.85(15) . . . . ? C18 Fe1 C1 C2 -176.88(12) . . . . ? C3 Fe1 C1 C2 38.01(11) . . . . ? C17 Fe1 C1 C2 152.0(13) . . . . ? C4 Fe1 C1 C2 81.50(12) . . . . ? C15 Fe1 C1 C6 27.69(16) . . . . ? C2 Fe1 C1 C6 121.99(19) . . . . ? C16 Fe1 C1 C6 65.27(19) . . . . ? C19 Fe1 C1 C6 -16.81(16) . . . . ? C5 Fe1 C1 C6 -119.16(19) . . . . ? C18 Fe1 C1 C6 -54.89(19) . . . . ? C3 Fe1 C1 C6 160.00(16) . . . . ? C17 Fe1 C1 C6 -86.0(13) . . . . ? C4 Fe1 C1 C6 -156.50(16) . . . . ? C5 C1 C2 C3 -0.7(2) . . . . ? C6 C1 C2 C3 -172.38(17) . . . . ? Fe1 C1 C2 C3 -60.65(13) . . . . ? C5 C1 C2 Fe1 59.98(13) . . . . ? C6 C1 C2 Fe1 -111.73(19) . . . . ? C1 Fe1 C2 C3 118.18(16) . . . . ? C15 Fe1 C2 C3 -138.92(11) . . . . ? C16 Fe1 C2 C3 -94.93(12) . . . . ? C19 Fe1 C2 C3 -177.55(12) . . . . ? C5 Fe1 C2 C3 80.18(12) . . . . ? C18 Fe1 C2 C3 167.5(16) . . . . ? C17 Fe1 C2 C3 -59.12(17) . . . . ? C4 Fe1 C2 C3 36.77(11) . . . . ? C15 Fe1 C2 C1 102.90(11) . . . . ? C16 Fe1 C2 C1 146.89(11) . . . . ? C19 Fe1 C2 C1 64.27(15) . . . . ? C5 Fe1 C2 C1 -38.00(11) . . . . ? C18 Fe1 C2 C1 49.3(17) . . . . ? C3 Fe1 C2 C1 -118.18(16) . . . . ? C17 Fe1 C2 C1 -177.30(13) . . . . ? C4 Fe1 C2 C1 -81.41(12) . . . . ? C1 C2 C3 C4 0.8(2) . . . . ? Fe1 C2 C3 C4 -58.82(13) . . . . ? C1 C2 C3 Fe1 59.63(12) . . . . ? C1 Fe1 C3 C2 -38.79(11) . . . . ? C15 Fe1 C3 C2 62.89(15) . . . . ? C16 Fe1 C3 C2 101.38(12) . . . . ? C19 Fe1 C3 C2 32.1(14) . . . . ? C5 Fe1 C3 C2 -83.14(12) . . . . ? C18 Fe1 C3 C2 -179.00(13) . . . . ? C17 Fe1 C3 C2 144.75(11) . . . . ? C4 Fe1 C3 C2 -120.57(16) . . . . ? C1 Fe1 C3 C4 81.78(12) . . . . ? C15 Fe1 C3 C4 -176.55(12) . . . . ? C2 Fe1 C3 C4 120.57(16) . . . . ? C16 Fe1 C3 C4 -138.06(12) . . . . ? C19 Fe1 C3 C4 152.6(13) . . . . ? C5 Fe1 C3 C4 37.42(12) . . . . ? C18 Fe1 C3 C4 -58.44(17) . . . . ? C17 Fe1 C3 C4 -94.69(12) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? Fe1 C3 C4 C5 -58.65(13) . . . . ? C2 C3 C4 Fe1 58.01(13) . . . . ? C1 Fe1 C4 C5 37.97(11) . . . . ? C15 Fe1 C4 C5 153.6(10) . . . . ? C2 Fe1 C4 C5 82.58(12) . . . . ? C16 Fe1 C4 C5 -177.01(12) . . . . ? C19 Fe1 C4 C5 -58.10(17) . . . . ? C18 Fe1 C4 C5 -95.10(12) . . . . ? C3 Fe1 C4 C5 119.52(16) . . . . ? C17 Fe1 C4 C5 -138.45(12) . . . . ? C1 Fe1 C4 C3 -81.55(12) . . . . ? C15 Fe1 C4 C3 34.1(11) . . . . ? C2 Fe1 C4 C3 -36.94(11) . . . . ? C16 Fe1 C4 C3 63.48(15) . . . . ? C19 Fe1 C4 C3 -177.62(12) . . . . ? C5 Fe1 C4 C3 -119.52(16) . . . . ? C18 Fe1 C4 C3 145.38(11) . . . . ? C17 Fe1 C4 C3 102.03(12) . . . . ? C3 C4 C5 C1 0.2(2) . . . . ? Fe1 C4 C5 C1 -58.73(13) . . . . ? C3 C4 C5 Fe1 58.95(13) . . . . ? C2 C1 C5 C4 0.3(2) . . . . ? C6 C1 C5 C4 172.28(17) . . . . ? Fe1 C1 C5 C4 59.86(13) . . . . ? C2 C1 C5 Fe1 -59.58(13) . . . . ? C6 C1 C5 Fe1 112.42(18) . . . . ? C1 Fe1 C5 C4 -119.33(15) . . . . ? C15 Fe1 C5 C4 -176.82(13) . . . . ? C2 Fe1 C5 C4 -81.05(12) . . . . ? C16 Fe1 C5 C4 26.4(10) . . . . ? C19 Fe1 C5 C4 145.72(11) . . . . ? C18 Fe1 C5 C4 101.96(12) . . . . ? C3 Fe1 C5 C4 -37.39(11) . . . . ? C17 Fe1 C5 C4 63.47(15) . . . . ? C15 Fe1 C5 C1 -57.48(16) . . . . ? C2 Fe1 C5 C1 38.28(11) . . . . ? C16 Fe1 C5 C1 145.7(10) . . . . ? C19 Fe1 C5 C1 -94.95(12) . . . . ? C18 Fe1 C5 C1 -138.71(11) . . . . ? C3 Fe1 C5 C1 81.94(11) . . . . ? C17 Fe1 C5 C1 -177.20(12) . . . . ? C4 Fe1 C5 C1 119.33(15) . . . . ? C7 O2 C6 O1 -25.8(2) . . . . ? C7 O2 C6 C1 154.55(15) . . . . ? C5 C1 C6 O1 3.7(3) . . . . ? C2 C1 C6 O1 174.12(18) . . . . ? Fe1 C1 C6 O1 88.7(2) . . . . ? C5 C1 C6 O2 -176.65(16) . . . . ? C2 C1 C6 O2 -6.2(3) . . . . ? Fe1 C1 C6 O2 -91.68(16) . . . . ? C6 O2 C7 C8 132.66(16) . . . . ? C6 O2 C7 C11 -108.61(16) . . . . ? C12 O4 C8 O3 75.5(2) . . . . ? C12 O4 C8 C7 -165.14(15) . . . . ? C9 O3 C8 O4 59.7(2) . . . . ? C9 O3 C8 C7 -60.36(18) . . . . ? O2 C7 C8 O4 57.47(18) . . . . ? C11 C7 C8 O4 -60.17(17) . . . . ? O2 C7 C8 O3 -179.85(13) . . . . ? C11 C7 C8 O3 62.50(18) . . . . ? C8 O3 C9 C13 177.41(14) . . . . ? C8 O3 C9 C10 55.1(2) . . . . ? O3 C9 C10 O6 -171.67(14) . . . . ? C13 C9 C10 O6 68.74(18) . . . . ? O3 C9 C10 C11 -50.4(2) . . . . ? C13 C9 C10 C11 -169.97(16) . . . . ? C14 O7 C11 C10 128.27(16) . . . . ? C14 O7 C11 C7 -113.34(16) . . . . ? O6 C10 C11 O7 -71.09(19) . . . . ? C9 C10 C11 O7 171.01(14) . . . . ? O6 C10 C11 C7 172.73(14) . . . . ? C9 C10 C11 C7 54.83(19) . . . . ? O2 C7 C11 O7 58.73(17) . . . . ? C8 C7 C11 O7 179.50(13) . . . . ? O2 C7 C11 C10 177.66(14) . . . . ? C8 C7 C11 C10 -61.57(18) . . . . ? O3 C9 C13 O5 -61.81(19) . . . . ? C10 C9 C13 O5 60.6(2) . . . . ? C11 O7 C14 O8 -19.9(3) . . . . ? C11 O7 C14 C15 158.28(14) . . . . ? O8 C14 C15 C16 6.4(3) . . . . ? O7 C14 C15 C16 -171.74(16) . . . . ? O8 C14 C15 C19 173.73(19) . . . . ? O7 C14 C15 C19 -4.5(3) . . . . ? O8 C14 C15 Fe1 89.1(2) . . . . ? O7 C14 C15 Fe1 -89.09(16) . . . . ? C1 Fe1 C15 C16 145.77(11) . . . . ? C2 Fe1 C15 C16 101.24(12) . . . . ? C19 Fe1 C15 C16 -119.19(14) . . . . ? C5 Fe1 C15 C16 -177.15(13) . . . . ? C18 Fe1 C15 C16 -81.20(12) . . . . ? C3 Fe1 C15 C16 63.26(14) . . . . ? C17 Fe1 C15 C16 -37.74(11) . . . . ? C4 Fe1 C15 C16 31.7(11) . . . . ? C1 Fe1 C15 C19 -95.03(11) . . . . ? C2 Fe1 C15 C19 -139.57(10) . . . . ? C16 Fe1 C15 C19 119.19(14) . . . . ? C5 Fe1 C15 C19 -57.96(16) . . . . ? C18 Fe1 C15 C19 37.99(10) . . . . ? C3 Fe1 C15 C19 -177.55(11) . . . . ? C17 Fe1 C15 C19 81.46(11) . . . . ? C4 Fe1 C15 C19 150.9(11) . . . . ? C1 Fe1 C15 C14 28.09(16) . . . . ? C2 Fe1 C15 C14 -16.45(15) . . . . ? C16 Fe1 C15 C14 -117.69(18) . . . . ? C19 Fe1 C15 C14 123.12(18) . . . . ? C5 Fe1 C15 C14 65.16(19) . . . . ? C18 Fe1 C15 C14 161.11(16) . . . . ? C3 Fe1 C15 C14 -54.43(18) . . . . ? C17 Fe1 C15 C14 -155.42(15) . . . . ? C4 Fe1 C15 C14 -86.0(11) . . . . ? C19 C15 C16 C17 0.8(2) . . . . ? C14 C15 C16 C17 170.26(16) . . . . ? Fe1 C15 C16 C17 60.41(13) . . . . ? C19 C15 C16 Fe1 -59.60(12) . . . . ? C14 C15 C16 Fe1 109.85(16) . . . . ? C1 Fe1 C16 C17 -177.36(13) . . . . ? C15 Fe1 C16 C17 -118.66(16) . . . . ? C2 Fe1 C16 C17 145.99(11) . . . . ? C19 Fe1 C16 C17 -80.64(12) . . . . ? C5 Fe1 C16 C17 40.4(10) . . . . ? C18 Fe1 C16 C17 -37.02(12) . . . . ? C3 Fe1 C16 C17 102.52(12) . . . . ? C4 Fe1 C16 C17 64.53(16) . . . . ? C1 Fe1 C16 C15 -58.70(16) . . . . ? C2 Fe1 C16 C15 -95.34(12) . . . . ? C19 Fe1 C16 C15 38.02(10) . . . . ? C5 Fe1 C16 C15 159.0(9) . . . . ? C18 Fe1 C16 C15 81.65(12) . . . . ? C3 Fe1 C16 C15 -138.82(11) . . . . ? C17 Fe1 C16 C15 118.66(16) . . . . ? C4 Fe1 C16 C15 -176.81(11) . . . . ? C15 C16 C17 C18 -0.7(2) . . . . ? Fe1 C16 C17 C18 58.69(14) . . . . ? C15 C16 C17 Fe1 -59.40(12) . . . . ? C1 Fe1 C17 C16 153.3(13) . . . . ? C15 Fe1 C17 C16 38.29(11) . . . . ? C2 Fe1 C17 C16 -56.74(17) . . . . ? C19 Fe1 C17 C16 82.85(12) . . . . ? C5 Fe1 C17 C16 -175.58(12) . . . . ? C18 Fe1 C17 C16 120.09(16) . . . . ? C3 Fe1 C17 C16 -94.02(12) . . . . ? C4 Fe1 C17 C16 -137.45(11) . . . . ? C1 Fe1 C17 C18 33.3(13) . . . . ? C15 Fe1 C17 C18 -81.80(12) . . . . ? C2 Fe1 C17 C18 -176.83(13) . . . . ? C16 Fe1 C17 C18 -120.09(16) . . . . ? C19 Fe1 C17 C18 -37.24(11) . . . . ? C5 Fe1 C17 C18 64.33(16) . . . . ? C3 Fe1 C17 C18 145.90(12) . . . . ? C4 Fe1 C17 C18 102.47(12) . . . . ? C16 C17 C18 C19 0.3(2) . . . . ? Fe1 C17 C18 C19 58.61(13) . . . . ? C16 C17 C18 Fe1 -58.26(13) . . . . ? C1 Fe1 C18 C17 -177.15(12) . . . . ? C15 Fe1 C18 C17 81.39(12) . . . . ? C2 Fe1 C18 C17 135.8(16) . . . . ? C16 Fe1 C18 C17 37.13(11) . . . . ? C19 Fe1 C18 C17 120.05(16) . . . . ? C5 Fe1 C18 C17 -137.92(12) . . . . ? C3 Fe1 C18 C17 -57.44(17) . . . . ? C4 Fe1 C18 C17 -94.32(12) . . . . ? C1 Fe1 C18 C19 62.79(15) . . . . ? C15 Fe1 C18 C19 -38.66(10) . . . . ? C2 Fe1 C18 C19 15.8(17) . . . . ? C16 Fe1 C18 C19 -82.92(11) . . . . ? C5 Fe1 C18 C19 102.03(12) . . . . ? C3 Fe1 C18 C19 -177.49(12) . . . . ? C17 Fe1 C18 C19 -120.05(16) . . . . ? C4 Fe1 C18 C19 145.62(11) . . . . ? C17 C18 C19 C15 0.2(2) . . . . ? Fe1 C18 C19 C15 59.35(12) . . . . ? C17 C18 C19 Fe1 -59.20(13) . . . . ? C16 C15 C19 C18 -0.59(19) . . . . ? C14 C15 C19 C18 -169.38(17) . . . . ? Fe1 C15 C19 C18 -60.25(12) . . . . ? C16 C15 C19 Fe1 59.66(12) . . . . ? C14 C15 C19 Fe1 -109.13(18) . . . . ? C1 Fe1 C19 C18 -139.42(11) . . . . ? C15 Fe1 C19 C18 118.25(15) . . . . ? C2 Fe1 C19 C18 -178.88(12) . . . . ? C16 Fe1 C19 C18 80.46(12) . . . . ? C5 Fe1 C19 C18 -95.11(12) . . . . ? C3 Fe1 C19 C18 150.9(14) . . . . ? C17 Fe1 C19 C18 37.00(11) . . . . ? C4 Fe1 C19 C18 -58.35(17) . . . . ? C1 Fe1 C19 C15 102.34(11) . . . . ? C2 Fe1 C19 C15 62.87(14) . . . . ? C16 Fe1 C19 C15 -37.78(10) . . . . ? C5 Fe1 C19 C15 146.64(10) . . . . ? C18 Fe1 C19 C15 -118.25(15) . . . . ? C3 Fe1 C19 C15 32.6(14) . . . . ? C17 Fe1 C19 C15 -81.25(11) . . . . ? C4 Fe1 C19 C15 -176.59(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.297 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.051