# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Peter Kenny' _publ_contact_author_email peter.kenny@dcu.ie _publ_section_title ; Synthesis, characterisation and biological evaluation of N-(ferrocenyl)naphthoyl amino acid esters as anti-cancer agents ; _publ_author_name P.Kenny # Attachment '- am6FcOMe.CIF' data_am6FcOMe _database_code_depnum_ccdc_archive 'CCDC 718596' #TrackingRef '- am6FcOMe.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; # CHEMICAL DATA _chemical_name_common methyl-6-ferrocenylnaphthalene-2-carboxylate _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 Fe O2' _chemical_formula_weight 370.21 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' # CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.7851(17) _cell_length_b 6.1301(7) _cell_length_c 18.161(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.273(3) _cell_angle_gamma 90.00 _cell_volume 1644.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1556 _cell_measurement_theta_min 4.49 _cell_measurement_theta_max 44.554 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.929 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7876 _exptl_absorpt_correction_T_max 0.8888 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1997' _exptl_special_details ; ? ; # EXPERIMENTAL DATA _diffrn_ambient_temperature 298(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 area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9115 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2883 _reflns_number_gt 2269 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? # REFINEMENT DATA _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^)+(0.0675P)^2^+0.3355P] 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 2883 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9841(4) -0.0087(13) 0.1835(2) 0.106(2) Uani 1 1 d . . . H1A H 1.0393 -0.0692 0.1635 0.127 Uiso 1 1 calc R . . C3 C 0.8449(3) 0.0283(10) 0.2259(2) 0.0816(15) Uani 1 1 d . . . H3A H 0.7824 -0.0009 0.2393 0.098 Uiso 1 1 calc R . . C4 C 0.8894(4) 0.2121(9) 0.2391(2) 0.0822(14) Uani 1 1 d . . . H4A H 0.8649 0.3413 0.2630 0.099 Uiso 1 1 calc R . . C5 C 0.9721(3) 0.1945(10) 0.2148(3) 0.0900(17) Uani 1 1 d . . . H5A H 1.0181 0.3095 0.2181 0.108 Uiso 1 1 calc R . . C2 C 0.8997(5) -0.1149(7) 0.1921(2) 0.0931(19) Uani 1 1 d . . . H2A H 0.8847 -0.2654 0.1779 0.112 Uiso 1 1 calc R . . C7 C 0.8892(3) 0.4078(6) 0.0579(2) 0.0584(10) Uani 1 1 d . . . H7A H 0.9256 0.5398 0.0661 0.070 Uiso 1 1 calc R . . C11 C 0.6819(2) 0.0657(5) 0.06907(15) 0.0405(7) Uani 1 1 d . . . C21 C 0.2711(2) -0.2100(6) 0.14837(18) 0.0517(9) Uani 1 1 d . . . C6 C 0.9183(2) 0.2150(6) 0.02307(18) 0.0568(9) Uani 1 1 d . . . H6A H 0.9778 0.1897 0.0026 0.068 Uiso 1 1 calc R . . C8 C 0.8001(2) 0.3781(5) 0.07951(19) 0.0496(8) Uani 1 1 d . . . H8A H 0.7637 0.4859 0.1049 0.060 Uiso 1 1 calc R . . C10 C 0.8456(2) 0.0665(6) 0.02326(17) 0.0486(8) Uani 1 1 d . . . H10A H 0.8466 -0.0820 0.0033 0.058 Uiso 1 1 calc R . . C18 C 0.4616(2) 0.1912(5) 0.15421(16) 0.0457(8) Uani 1 1 d . . . H18A H 0.4726 0.3304 0.1728 0.055 Uiso 1 1 calc R . . C16 C 0.3610(2) -0.1153(5) 0.13574(16) 0.0438(8) Uani 1 1 d . . . C15 C 0.4259(2) -0.2247(6) 0.09850(16) 0.0427(7) Uani 1 1 d . . . H15A H 0.4133 -0.3634 0.0801 0.051 Uiso 1 1 calc R . . C19 C 0.5303(2) 0.0803(5) 0.11617(15) 0.0388(7) Uani 1 1 d . . . C20 C 0.6155(2) 0.1727(5) 0.10636(16) 0.0432(8) Uani 1 1 d . . . H20A H 0.6279 0.3107 0.1256 0.052 Uiso 1 1 calc R . . C14 C 0.5112(2) -0.1313(5) 0.08769(16) 0.0380(7) Uani 1 1 d . . . C22 C 0.1791(2) -0.5243(7) 0.1357(2) 0.0646(10) Uani 1 1 d . . . H22A H 0.1810 -0.6693 0.1159 0.097 Uiso 1 1 calc R . . H22B H 0.1304 -0.4446 0.1117 0.097 Uiso 1 1 calc R . . H22C H 0.1696 -0.5314 0.1876 0.097 Uiso 1 1 calc R . . C9 C 0.7710(2) 0.1644(5) 0.05761(16) 0.0424(8) Uani 1 1 d . . . C17 C 0.3801(2) 0.0954(5) 0.16355(17) 0.0467(8) Uani 1 1 d . . . H17A H 0.3361 0.1699 0.1887 0.056 Uiso 1 1 calc R . . C13 C 0.5792(2) -0.2391(5) 0.04964(16) 0.0433(7) Uani 1 1 d . . . H13A H 0.5679 -0.3777 0.0306 0.052 Uiso 1 1 calc R . . C12 C 0.6610(2) -0.1449(5) 0.04018(17) 0.0441(8) Uani 1 1 d . . . H12A H 0.7043 -0.2196 0.0143 0.053 Uiso 1 1 calc R . . O1 O 0.21100(18) -0.1186(5) 0.17828(17) 0.0771(8) Uani 1 1 d . . . O2 O 0.26333(16) -0.4156(4) 0.12347(13) 0.0591(6) Uani 1 1 d . . . Fe1 Fe 0.88233(3) 0.15134(7) 0.12883(2) 0.03975(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.076(3) 0.179(6) 0.063(3) 0.032(4) 0.009(2) 0.086(4) C3 0.059(3) 0.132(5) 0.052(2) 0.034(3) -0.006(2) -0.024(3) C4 0.107(4) 0.091(4) 0.047(2) -0.008(2) -0.017(2) 0.019(3) C5 0.066(3) 0.122(5) 0.079(3) 0.029(3) -0.035(3) -0.039(3) C2 0.181(6) 0.039(2) 0.056(3) 0.0108(19) -0.043(3) 0.001(3) C7 0.066(2) 0.047(2) 0.062(2) 0.0178(18) 0.0038(19) -0.0075(18) C11 0.0460(18) 0.0401(17) 0.0347(16) 0.0014(14) -0.0084(13) 0.0083(14) C21 0.053(2) 0.058(2) 0.0434(19) 0.0049(17) -0.0023(16) 0.0051(18) C6 0.062(2) 0.061(2) 0.049(2) 0.0107(18) 0.0146(17) -0.0014(19) C8 0.058(2) 0.0349(18) 0.055(2) 0.0065(15) 0.0002(17) 0.0066(15) C10 0.057(2) 0.050(2) 0.0393(18) -0.0017(15) 0.0032(15) -0.0007(17) C18 0.058(2) 0.0417(19) 0.0377(17) -0.0071(14) -0.0012(14) 0.0114(15) C16 0.0480(19) 0.049(2) 0.0342(16) 0.0042(14) -0.0012(14) 0.0086(15) C15 0.0493(19) 0.0415(18) 0.0369(16) 0.0004(14) -0.0039(14) 0.0042(15) C19 0.0491(19) 0.0370(17) 0.0296(15) -0.0004(13) -0.0066(13) 0.0081(14) C20 0.056(2) 0.0365(18) 0.0366(16) -0.0035(14) -0.0074(14) 0.0041(15) C14 0.0472(18) 0.0349(17) 0.0313(15) 0.0008(13) -0.0066(13) 0.0082(14) C22 0.057(2) 0.072(3) 0.065(2) 0.005(2) 0.0007(18) -0.007(2) C9 0.0477(19) 0.0433(19) 0.0356(16) 0.0027(14) -0.0061(14) 0.0064(15) C17 0.052(2) 0.048(2) 0.0404(17) -0.0008(15) 0.0042(14) 0.0152(16) C13 0.0500(19) 0.0366(18) 0.0427(17) -0.0069(14) -0.0054(14) 0.0070(16) C12 0.048(2) 0.0424(19) 0.0417(17) -0.0051(14) -0.0017(14) 0.0140(15) O1 0.0593(17) 0.076(2) 0.097(2) -0.0134(16) 0.0263(15) 0.0063(14) O2 0.0567(15) 0.0567(16) 0.0640(16) -0.0030(13) 0.0058(12) -0.0027(12) Fe1 0.0406(3) 0.0383(3) 0.0401(3) 0.0039(2) -0.00144(19) -0.00174(19) # MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C5 1.384(8) . no C1 C2 1.421(7) . no C1 Fe1 2.023(4) . no C3 C4 1.322(7) . no C3 C2 1.359(7) . no C3 Fe1 2.016(4) . no C4 C5 1.319(7) . no C4 Fe1 2.035(4) . no C5 Fe1 2.027(4) . no C2 Fe1 2.006(4) . no C7 C8 1.401(5) . no C7 C6 1.416(5) . no C7 Fe1 2.037(3) . no C11 C20 1.380(4) . no C11 C12 1.423(4) . no C11 C9 1.472(4) . no C21 O1 1.198(4) . yes C21 O2 1.343(4) . yes C21 C16 1.477(5) . no C6 C10 1.409(5) . no C6 Fe1 2.051(3) . no C8 C9 1.430(4) . no C8 Fe1 2.031(3) . no C10 C9 1.422(5) . no C10 Fe1 2.039(3) . no C18 C17 1.357(5) . no C18 C19 1.424(4) . no C16 C15 1.372(4) . no C16 C27 1.411(4) . no C15 C14 1.406(4) . no C19 C20 1.400(4) . no C19 C14 1.421(4) . no C14 C13 1.407(4) . no C22 O2 1.438(4) . yes C9 Fe1 2.054(3) . no C13 C12 1.357(4) . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C1 C2 103.9(4) . . no C5 C1 Fe1 70.1(2) . . no C2 C1 Fe1 68.7(2) . . no C4 C3 C2 109.3(4) . . no C4 C3 Fe1 71.8(3) . . no C2 C3 Fe1 69.9(2) . . no C5 C4 C3 109.4(5) . . no C5 C4 Fe1 70.7(3) . . no C3 C4 Fe1 70.2(2) . . no C4 C5 C1 110.2(5) . . no C4 C5 Fe1 71.4(2) . . no C1 C5 Fe1 69.9(2) . . no C3 C2 C1 107.2(4) . . no C3 C2 Fe1 70.6(2) . . no C1 C2 Fe1 70.0(2) . . no C8 C7 C6 108.8(3) . . no C8 C7 Fe1 69.62(19) . . no C6 C7 Fe1 70.2(2) . . no C20 C11 C12 117.7(3) . . no C20 C11 C9 122.1(3) . . no C12 C11 C9 120.2(3) . . no O1 C21 O2 122.5(4) . . yes O1 C21 C16 125.1(4) . . yes O2 C21 C16 112.4(3) . . yes C10 C6 C7 107.0(3) . . no C10 C6 Fe1 69.41(18) . . no C7 C6 Fe1 69.2(2) . . no C7 C8 C9 108.5(3) . . no C7 C8 Fe1 70.1(2) . . no C9 C8 Fe1 70.39(17) . . no C6 C10 C9 109.5(3) . . no C6 C10 Fe1 70.29(19) . . no C9 C10 Fe1 70.24(18) . . no C17 C18 C19 120.6(3) . . no C15 C16 C17 119.3(3) . . no C15 C16 C21 122.5(3) . . yes C17 C16 C21 118.2(3) . . yes C16 C15 C14 121.3(3) . . no C20 C19 C14 119.3(3) . . no C20 C19 C18 122.2(3) . . no C14 C19 C18 118.5(3) . . no C11 C20 C19 122.1(3) . . no C15 C14 C13 122.6(3) . . no C15 C14 C19 119.2(3) . . no C13 C14 C19 118.2(3) . . no C10 C9 C8 106.2(3) . . no C10 C9 C11 127.1(3) . . no C8 C9 C11 126.8(3) . . no C10 C9 Fe1 69.11(18) . . no C8 C9 Fe1 68.63(18) . . no C11 C9 Fe1 126.5(2) . . no C18 C17 C16 121.2(3) . . no C12 C13 C14 121.3(3) . . no C13 C12 C11 121.4(3) . . no C21 O2 C22 116.5(3) . . yes C2 Fe1 C3 39.5(2) . . no C2 Fe1 C1 41.3(2) . . no C3 Fe1 C1 67.27(19) . . no C2 Fe1 C5 66.43(19) . . no C3 Fe1 C5 64.46(18) . . no C1 Fe1 C5 40.0(2) . . no C2 Fe1 C8 150.5(2) . . no C3 Fe1 C8 117.49(18) . . no C1 Fe1 C8 165.6(3) . . no C5 Fe1 C8 127.8(2) . . no C2 Fe1 C4 65.50(19) . . no C3 Fe1 C4 38.1(2) . . no C1 Fe1 C4 66.2(2) . . no C5 Fe1 C4 37.91(19) . . no C8 Fe1 C4 108.39(17) . . no C2 Fe1 C7 168.8(2) . . no C3 Fe1 C7 149.8(2) . . no C1 Fe1 C7 129.0(2) . . no C5 Fe1 C7 109.81(17) . . no C8 Fe1 C7 40.28(14) . . no C4 Fe1 C7 118.60(19) . . no C2 Fe1 C10 110.71(16) . . no C3 Fe1 C10 130.91(19) . . no C1 Fe1 C10 120.2(2) . . no C5 Fe1 C10 154.1(2) . . no C8 Fe1 C10 68.14(14) . . no C4 Fe1 C10 166.68(19) . . no C7 Fe1 C10 67.71(15) . . no C2 Fe1 C6 131.2(2) . . no C3 Fe1 C6 168.8(2) . . no C1 Fe1 C6 109.68(16) . . no C5 Fe1 C6 120.71(18) . . no C8 Fe1 C6 68.27(15) . . no C4 Fe1 C6 151.8(2) . . no C7 Fe1 C6 40.53(15) . . no C10 Fe1 C6 40.30(14) . . no C2 Fe1 C9 118.24(18) . . no C3 Fe1 C9 108.92(14) . . no C1 Fe1 C9 152.8(3) . . no C5 Fe1 C9 164.6(2) . . no C8 Fe1 C9 40.98(13) . . no C4 Fe1 C9 128.41(18) . . no C7 Fe1 C9 68.33(14) . . no C10 Fe1 C9 40.65(13) . . no C6 Fe1 C9 68.54(14) . . no _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.439 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.066 # Attachment '- am3FcOMe.CIF' data_am3FcOM _database_code_depnum_ccdc_archive 'CCDC 775339' #TrackingRef '- am3FcOMe.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; # CHEMICAL DATA _chemical_name_common methyl-3-ferrocenylnaphthalene-2-carboxylate _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 Fe O2' _chemical_formula_sum 'C22 H18 Fe O2' _chemical_formula_weight 370.21 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' # CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 13.9797(15) _cell_length_b 8.7249(9) _cell_length_c 13.9843(15) _cell_angle_alpha 90.00 _cell_angle_beta 103.111(2) _cell_angle_gamma 90.00 _cell_volume 1661.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 7801 _cell_measurement_theta_min 5.545 _cell_measurement_theta_max 49.847 _exptl_crystal_description blocks _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.920 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8027 _exptl_absorpt_correction_T_max 0.8898 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1997' _exptl_special_details ; ? ; # EXPERIMENTAL DATA _diffrn_ambient_temperature 273(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, CCD Area Detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17252 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2927 _reflns_number_gt 2673 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? # REFINEMENT DATA _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^)+(0.0559P)^2^+0.3704P] 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 2927 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Fe2 Fe 0.368212(17) 0.17459(3) 0.353977(16) 0.03314(11) Uani 1 1 d . . . O24 O 0.10268(11) 0.09366(15) 0.12108(10) 0.0523(3) Uani 1 1 d . . . O25 O 0.06344(11) 0.19947(16) 0.25251(11) 0.0523(4) Uani 1 1 d . . . C1 C 0.48500(17) 0.0348(3) 0.35314(17) 0.0616(6) Uani 1 1 d . . . H1A H 0.5498 0.0413 0.3981 0.074 Uiso 1 1 d R . . C2 C 0.04691(18) -0.0417(2) 0.13413(18) 0.0651(6) Uani 1 1 d . . . H2A H 0.0576 -0.1203 0.0897 0.098 Uiso 1 1 calc R . . H2B H -0.0217 -0.0167 0.1209 0.098 Uiso 1 1 calc R . . H2C H 0.0679 -0.0777 0.2005 0.098 Uiso 1 1 calc R . . C3 C 0.45553(16) 0.1130(3) 0.26236(16) 0.0553(5) Uani 1 1 d . . . H3A H 0.4962 0.1817 0.2328 0.066 Uiso 1 1 d R . . C4 C 0.26969(15) 0.7552(2) 0.06921(14) 0.0472(5) Uani 1 1 d . . . H4A H 0.3193 0.8081 0.1120 0.057 Uiso 1 1 calc R . . C5 C 0.32854(14) 0.2491(2) 0.47825(12) 0.0416(4) Uani 1 1 d . . . H5A H 0.3266 0.1864 0.5359 0.050 Uiso 1 1 d R . . C6 C 0.32614(17) -0.0296(2) 0.28687(14) 0.0495(5) Uani 1 1 d . . . H6A H 0.2609 -0.0763 0.2777 0.059 Uiso 1 1 d R . . C7 C 0.15978(16) 0.7301(2) -0.08972(14) 0.0497(5) Uani 1 1 d . . . H7A H 0.1353 0.7688 -0.1525 0.060 Uiso 1 1 calc R . . C8 C 0.12401(14) 0.5962(2) -0.06224(13) 0.0439(4) Uani 1 1 d . . . H8A H 0.0764 0.5427 -0.1071 0.053 Uiso 1 1 calc R . . C10 C 0.23402(18) 0.8104(2) -0.02312(16) 0.0529(5) Uani 1 1 d . . . H10A H 0.2587 0.9014 -0.0424 0.064 Uiso 1 1 calc R . . C11 C 0.35673(16) 0.0715(2) 0.22156(14) 0.0477(5) Uani 1 1 d . . . H11A H 0.3166 0.1074 0.1588 0.057 Uiso 1 1 d R . . C12 C 0.26631(13) 0.55819(19) 0.19611(13) 0.0370(4) Uani 1 1 d . . . H12A H 0.3144 0.6126 0.2399 0.044 Uiso 1 1 calc R . . C13 C 0.4054(2) -0.0520(2) 0.36812(16) 0.0581(6) Uani 1 1 d . . . H13A H 0.4049 -0.1166 0.4253 0.070 Uiso 1 1 d R . . C14 C 0.10401(13) 0.2066(2) 0.18577(13) 0.0384(4) Uani 1 1 d . . . C15 C 0.23267(12) 0.42398(18) 0.22797(12) 0.0323(4) Uani 1 1 d . . . C16 C 0.23205(13) 0.61817(19) 0.10075(13) 0.0364(4) Uani 1 1 d . . . C17 C 0.12303(12) 0.4000(2) 0.06648(13) 0.0370(4) Uani 1 1 d . . . H17A H 0.0753 0.3446 0.0230 0.044 Uiso 1 1 calc R . . C19 C 0.15618(13) 0.34503(19) 0.15978(13) 0.0347(4) Uani 1 1 d . . . C20 C 0.38367(13) 0.4051(2) 0.37064(13) 0.0392(4) Uani 1 1 d . . . H20A H 0.4265 0.4703 0.3413 0.047 Uiso 1 1 d R . . C21 C 0.28336(12) 0.36672(19) 0.32647(12) 0.0333(4) Uani 1 1 d . . . C22 C 0.41031(15) 0.3321(2) 0.46342(14) 0.0432(4) Uani 1 1 d . . . H22A H 0.4748 0.3376 0.5090 0.052 Uiso 1 1 d R . . C23 C 0.15832(12) 0.53720(19) 0.03358(12) 0.0361(4) Uani 1 1 d . . . C28 C 0.25012(13) 0.2702(2) 0.39513(12) 0.0371(4) Uani 1 1 d . . . H28D H 0.1846 0.2244 0.3857 0.044 Uiso 1 1 d 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 Fe2 0.03728(17) 0.03257(17) 0.02990(16) -0.00125(9) 0.00833(11) 0.00213(9) O24 0.0637(8) 0.0374(7) 0.0561(8) -0.0056(6) 0.0144(7) -0.0141(6) O25 0.0506(8) 0.0571(8) 0.0523(8) 0.0018(6) 0.0180(7) -0.0132(6) C1 0.0539(12) 0.0677(14) 0.0604(13) -0.0085(11) 0.0073(10) 0.0257(11) C2 0.0757(15) 0.0421(11) 0.0722(15) -0.0013(10) 0.0057(12) -0.0233(11) C3 0.0594(13) 0.0559(12) 0.0597(13) -0.0068(10) 0.0329(11) 0.0085(10) C4 0.0605(12) 0.0339(10) 0.0479(11) -0.0007(8) 0.0138(9) -0.0050(9) C5 0.0555(11) 0.0414(10) 0.0294(8) -0.0025(7) 0.0131(8) 0.0031(8) C6 0.0672(13) 0.0347(9) 0.0484(11) -0.0102(8) 0.0165(10) -0.0011(9) C7 0.0581(12) 0.0514(12) 0.0410(10) 0.0123(9) 0.0142(9) 0.0109(9) C8 0.0441(10) 0.0479(11) 0.0399(10) 0.0026(8) 0.0096(8) 0.0078(8) C10 0.0730(14) 0.0368(10) 0.0541(12) 0.0099(9) 0.0250(11) 0.0020(9) C11 0.0657(12) 0.0438(10) 0.0349(9) -0.0051(8) 0.0140(9) 0.0112(9) C12 0.0419(9) 0.0311(9) 0.0369(9) -0.0040(7) 0.0070(7) -0.0028(7) C13 0.0890(16) 0.0397(11) 0.0465(12) 0.0044(9) 0.0174(11) 0.0203(11) C14 0.0331(9) 0.0383(9) 0.0405(10) 0.0021(7) 0.0020(8) -0.0025(7) C15 0.0361(8) 0.0284(8) 0.0337(8) -0.0028(6) 0.0104(7) 0.0021(6) C16 0.0440(9) 0.0291(8) 0.0381(9) -0.0004(7) 0.0134(7) 0.0039(7) C17 0.0332(8) 0.0382(9) 0.0388(9) -0.0029(7) 0.0066(7) -0.0015(7) C19 0.0324(8) 0.0324(9) 0.0401(9) 0.0000(7) 0.0100(7) 0.0019(7) C20 0.0430(9) 0.0344(9) 0.0393(10) -0.0043(7) 0.0074(8) -0.0071(7) C21 0.0386(9) 0.0281(8) 0.0341(9) -0.0046(7) 0.0101(7) 0.0002(7) C22 0.0495(11) 0.0412(10) 0.0347(10) -0.0073(7) 0.0010(8) -0.0020(8) C23 0.0358(9) 0.0372(9) 0.0370(9) 0.0002(7) 0.0120(7) 0.0056(7) C28 0.0411(9) 0.0370(9) 0.0358(9) -0.0021(7) 0.0143(7) 0.0009(7) # MOLECULAR GEOMETRY _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 Fe2 C20 2.0308(18) . ? Fe2 C11 2.0320(18) . ? Fe2 C3 2.0322(19) . ? Fe2 C6 2.0372(19) . ? Fe2 C21 2.0391(17) . ? Fe2 C1 2.040(2) . ? Fe2 C22 2.0417(18) . ? Fe2 C13 2.042(2) . ? Fe2 C28 2.0454(17) . ? Fe2 C5 2.0465(17) . ? O24 C14 1.335(2) . ? O24 C2 1.449(2) . ? O25 C14 1.199(2) . ? C1 C13 1.400(4) . ? C1 C3 1.417(3) . ? C1 H1A 0.9799 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C11 1.416(3) . ? C3 H3A 0.9800 . ? C4 C10 1.362(3) . ? C4 C16 1.416(3) . ? C4 H4A 0.9300 . ? C5 C22 1.407(3) . ? C5 C28 1.417(3) . ? C5 H5A 0.9799 . ? C6 C11 1.404(3) . ? C6 C13 1.410(3) . ? C6 H6A 0.9800 . ? C7 C8 1.360(3) . ? C7 C10 1.413(3) . ? C7 H7A 0.9300 . ? C8 C23 1.414(2) . ? C8 H8A 0.9300 . ? C10 H10A 0.9300 . ? C11 H11A 0.9800 . ? C12 C15 1.373(2) . ? C12 C16 1.411(2) . ? C12 H12A 0.9300 . ? C13 H13A 0.9800 . ? C14 C19 1.497(2) . ? C15 C19 1.437(2) . ? C15 C21 1.485(2) . ? C16 C23 1.416(2) . ? C17 C19 1.368(2) . ? C17 C23 1.411(2) . ? C17 H17A 0.9300 . ? C20 C22 1.417(3) . ? C20 C21 1.438(2) . ? C20 H20A 0.9800 . ? C21 C28 1.431(2) . ? C22 H22A 0.9800 . ? C28 H28D 0.9799 . ? 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 C20 Fe2 C11 121.83(8) . . ? C20 Fe2 C3 105.72(9) . . ? C11 Fe2 C3 40.79(9) . . ? C20 Fe2 C6 158.61(8) . . ? C11 Fe2 C6 40.38(8) . . ? C3 Fe2 C6 68.30(9) . . ? C20 Fe2 C21 41.37(7) . . ? C11 Fe2 C21 105.64(7) . . ? C3 Fe2 C21 120.36(8) . . ? C6 Fe2 C21 122.49(8) . . ? C20 Fe2 C1 121.89(9) . . ? C11 Fe2 C1 68.16(9) . . ? C3 Fe2 C1 40.74(9) . . ? C6 Fe2 C1 67.82(10) . . ? C21 Fe2 C1 157.28(9) . . ? C20 Fe2 C22 40.74(7) . . ? C11 Fe2 C22 158.56(8) . . ? C3 Fe2 C22 122.57(9) . . ? C6 Fe2 C22 159.71(8) . . ? C21 Fe2 C22 69.18(7) . . ? C1 Fe2 C22 108.16(9) . . ? C20 Fe2 C13 158.35(10) . . ? C11 Fe2 C13 68.01(8) . . ? C3 Fe2 C13 68.21(9) . . ? C6 Fe2 C13 40.43(9) . . ? C21 Fe2 C13 159.81(9) . . ? C1 Fe2 C13 40.12(10) . . ? C22 Fe2 C13 123.71(8) . . ? C20 Fe2 C28 68.61(7) . . ? C11 Fe2 C28 122.35(8) . . ? C3 Fe2 C28 157.49(8) . . ? C6 Fe2 C28 108.62(8) . . ? C21 Fe2 C28 41.03(7) . . ? C1 Fe2 C28 160.66(9) . . ? C22 Fe2 C28 68.18(8) . . ? C13 Fe2 C28 124.88(9) . . ? C20 Fe2 C5 68.28(7) . . ? C11 Fe2 C5 159.06(8) . . ? C3 Fe2 C5 159.50(9) . . ? C6 Fe2 C5 124.30(8) . . ? C21 Fe2 C5 68.95(7) . . ? C1 Fe2 C5 124.49(9) . . ? C22 Fe2 C5 40.28(8) . . ? C13 Fe2 C5 109.73(8) . . ? C28 Fe2 C5 40.53(7) . . ? C14 O24 C2 116.20(16) . . ? C13 C1 C3 108.35(19) . . ? C13 C1 Fe2 70.04(12) . . ? C3 C1 Fe2 69.33(11) . . ? C13 C1 H1A 125.8 . . ? C3 C1 H1A 125.8 . . ? Fe2 C1 H1A 125.9 . . ? O24 C2 H2A 109.5 . . ? O24 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? O24 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C11 C3 C1 107.3(2) . . ? C11 C3 Fe2 69.59(11) . . ? C1 C3 Fe2 69.93(12) . . ? C11 C3 H3A 126.3 . . ? C1 C3 H3A 126.4 . . ? Fe2 C3 H3A 126.4 . . ? C10 C4 C16 120.77(18) . . ? C10 C4 H4A 119.6 . . ? C16 C4 H4A 119.6 . . ? C22 C5 C28 108.38(16) . . ? C22 C5 Fe2 69.68(10) . . ? C28 C5 Fe2 69.70(10) . . ? C22 C5 H5A 125.7 . . ? C28 C5 H5A 125.9 . . ? Fe2 C5 H5A 125.8 . . ? C11 C6 C13 108.1(2) . . ? C11 C6 Fe2 69.61(11) . . ? C13 C6 Fe2 69.99(11) . . ? C11 C6 H6A 126.0 . . ? C13 C6 H6A 125.9 . . ? Fe2 C6 H6A 125.9 . . ? C8 C7 C10 120.13(18) . . ? C8 C7 H7A 119.9 . . ? C10 C7 H7A 119.9 . . ? C7 C8 C23 120.86(18) . . ? C7 C8 H8A 119.6 . . ? C23 C8 H8A 119.6 . . ? C4 C10 C7 120.37(18) . . ? C4 C10 H10A 119.8 . . ? C7 C10 H10A 119.8 . . ? C6 C11 C3 108.15(19) . . ? C6 C11 Fe2 70.01(11) . . ? C3 C11 Fe2 69.61(11) . . ? C6 C11 H11A 125.9 . . ? C3 C11 H11A 125.9 . . ? Fe2 C11 H11A 125.9 . . ? C15 C12 C16 123.70(16) . . ? C15 C12 H12A 118.1 . . ? C16 C12 H12A 118.1 . . ? C1 C13 C6 108.10(19) . . ? C1 C13 Fe2 69.85(12) . . ? C6 C13 Fe2 69.59(11) . . ? C1 C13 H13A 126.0 . . ? C6 C13 H13A 125.9 . . ? Fe2 C13 H13A 125.9 . . ? O25 C14 O24 123.55(16) . . ? O25 C14 C19 125.00(17) . . ? O24 C14 C19 111.32(15) . . ? C12 C15 C19 116.84(15) . . ? C12 C15 C21 117.46(15) . . ? C19 C15 C21 125.51(15) . . ? C12 C16 C23 118.80(16) . . ? C12 C16 C4 122.47(16) . . ? C23 C16 C4 118.72(16) . . ? C19 C17 C23 122.69(16) . . ? C19 C17 H17A 118.7 . . ? C23 C17 H17A 118.7 . . ? C17 C19 C15 120.33(16) . . ? C17 C19 C14 115.82(16) . . ? C15 C19 C14 123.75(15) . . ? C22 C20 C21 108.46(16) . . ? C22 C20 Fe2 70.05(10) . . ? C21 C20 Fe2 69.62(10) . . ? C22 C20 H20A 125.8 . . ? C21 C20 H20A 125.7 . . ? Fe2 C20 H20A 125.8 . . ? C28 C21 C20 106.40(15) . . ? C28 C21 C15 131.35(15) . . ? C20 C21 C15 122.25(15) . . ? C28 C21 Fe2 69.72(10) . . ? C20 C21 Fe2 69.00(10) . . ? C15 C21 Fe2 125.88(11) . . ? C5 C22 C20 108.21(16) . . ? C5 C22 Fe2 70.04(10) . . ? C20 C22 Fe2 69.22(10) . . ? C5 C22 H22A 126.0 . . ? C20 C22 H22A 125.8 . . ? Fe2 C22 H22A 125.9 . . ? C17 C23 C8 123.31(16) . . ? C17 C23 C16 117.57(15) . . ? C8 C23 C16 119.12(16) . . ? C5 C28 C21 108.55(16) . . ? C5 C28 Fe2 69.77(10) . . ? C21 C28 Fe2 69.25(9) . . ? C5 C28 H28D 125.7 . . ? C21 C28 H28D 125.8 . . ? Fe2 C28 H28D 125.8 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.246 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.049