# Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1476 loop_ _publ_author_name 'TOP, Siden' _publ_contact_author_name 'TOP, Siden' _publ_contact_author_email siden-top@chimie-paristech.fr _publ_section_title ; Facile synthesis and strong antiproliferative activity of disubstituted diphenylmethylidenyl-[3]ferrocenophanes on breast and prostate cancer cell lines ; # Attachment '- gormen.cif' data_compound_5 _database_code_depnum_ccdc_archive 'CCDC 768981' #TrackingRef '- gormen.cif' _audit_creation_date 10-02-09 _audit_creation_method CRYSTALS_ver_12.87 _chemical_name_systematic ; 1-[diphenyl-methylidenyl] -[3]ferrocenophane ; _chemical_melting_point 'not determined' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; ? ; _cell_length_a 5.8601(9) _cell_length_b 31.829(4) _cell_length_c 40.783(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 7606.9(17) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'F 2 d d ' _symmetry_space_group_name_Hall 'F -2 d 2' loop_ _symmetry_equiv_pos_as_xyz x,y,z x,y+1/2,z+1/2 x+1/2,y,z+1/2 x+1/2,y+1/2,z x,-y,-z x,-y+1/2,-z+1/2 x+1/2,-y,-z+1/2 x+1/2,-y+1/2,-z x+1/4,-y+1/4,z+1/4 x+1/4,-y+3/4,z+3/4 x+3/4,-y+1/4,z+3/4 x+3/4,-y+3/4,z+1/4 x+1/4,y+1/4,-z+1/4 x+1/4,y+3/4,-z+3/4 x+3/4,y+1/4,-z+3/4 x+3/4,y+3/4,-z+1/4 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Fe 0.3463 0.8444 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805 1.0369 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 16 # Given Formula = C26 H22 Fe1 # Dc = 1.36 Fooo = 3264.00 Mu = 8.00 M = 390.31 # Found Formula = C26 H22 Fe1 # Dc = 1.36 FOOO = 3264.00 Mu = 8.00 M = 390.31 _chemical_formula_sum 'C26 H22 Fe1' _chemical_formula_moiety 'C26 H22 Fe1' _chemical_compound_source synthesized _chemical_formula_weight 390.31 _cell_measurement_reflns_used 138 _cell_measurement_theta_min 4 _cell_measurement_theta_max 22 _cell_measurement_temperature 200 _exptl_crystal_description cube _exptl_crystal_colour yellow _exptl_crystal_size_min 0.140 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_max 0.150 _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 3264 _exptl_absorpt_coefficient_mu 0.800 # Sheldrick geometric approximatio 0.89 0.89 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.89 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material CRYSTALS _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 16586 _reflns_number_total 4545 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections without Friedels Law is 4545 # Number of reflections with Friedels Law is 3025 # Theoretical number of reflections is about 2774 _diffrn_reflns_theta_min 1.997 _diffrn_reflns_theta_max 30.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.000 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -54 _diffrn_reflns_limit_l_max 56 _reflns_limit_h_min -5 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 44 _reflns_limit_l_min 0 _reflns_limit_l_max 56 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.81 _refine_diff_density_max 0.69 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 4531 _refine_ls_number_restraints 1 _refine_ls_number_parameters 245 _oxford_refine_ls_R_factor_ref 0.0613 _refine_ls_wR_factor_ref 0.0736 _refine_ls_goodness_of_fit_ref 0.9642 _refine_ls_shift/su_max 0.0011485 _refine_ls_shift/su_mean 2.3101988 # The values computed from all data _oxford_reflns_number_all 4531 _refine_ls_R_factor_all 0.0613 _refine_ls_wR_factor_all 0.0736 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3488 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_gt 0.0655 _refine_ls_abs_structure_Flack 0.06(4) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.01P)^2^ +20.94P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Fe1 Fe 0.60711(13) 0.349845(10) 0.469008(8) 0.0210 1.0000 Uani . . . . . . . C1 C 0.6156(6) 0.29750(7) 0.44051(5) 0.0201 1.0000 Uani . . . . . . . C2 C 0.8431(5) 0.30902(7) 0.45056(6) 0.0230 1.0000 Uani . . . . . . . C3 C 0.8508(6) 0.30783(8) 0.48582(6) 0.0267 1.0000 Uani . . . . . . . C4 C 0.6324(6) 0.29567(7) 0.49753(6) 0.0260 1.0000 Uani . . . . . . . C5 C 0.4857(5) 0.28896(7) 0.46986(6) 0.0225 1.0000 Uani . . . . . . . C6 C 0.4568(5) 0.38978(8) 0.43663(6) 0.0255 1.0000 Uani . . . . . . . C7 C 0.3234(5) 0.38789(8) 0.46626(7) 0.0287 1.0000 Uani . . . . . . . C8 C 0.4663(6) 0.40106(8) 0.49292(7) 0.0316 1.0000 Uani . . . . . . . C9 C 0.6835(5) 0.41170(8) 0.48032(7) 0.0293 1.0000 Uani . . . . . . . C10 C 0.6801(5) 0.40508(8) 0.44540(7) 0.0274 1.0000 Uani . . . . . . . C11 C 0.5233(5) 0.29742(8) 0.40611(6) 0.0222 1.0000 Uani . . . . . . . C12 C 0.5358(5) 0.33980(8) 0.38822(6) 0.0269 1.0000 Uani . . . . . . . C13 C 0.3849(5) 0.37527(7) 0.40279(6) 0.0289 1.0000 Uani . . . . . . . C14 C 0.4350(5) 0.26248(8) 0.39207(6) 0.0220 1.0000 Uani . . . . . . . C15 C 0.4485(5) 0.21932(8) 0.40778(6) 0.0219 1.0000 Uani . . . . . . . C16 C 0.2664(5) 0.19102(8) 0.40467(6) 0.0270 1.0000 Uani . . . . . . . C17 C 0.2805(5) 0.15063(9) 0.41877(7) 0.0332 1.0000 Uani . . . . . . . C18 C 0.4737(6) 0.13809(8) 0.43554(7) 0.0329 1.0000 Uani . . . . . . . C19 C 0.6576(5) 0.16561(9) 0.43828(6) 0.0310 1.0000 Uani . . . . . . . C20 C 0.6457(5) 0.20588(8) 0.42440(6) 0.0259 1.0000 Uani . . . . . . . C21 C 0.3169(5) 0.26341(7) 0.35924(6) 0.0250 1.0000 Uani . . . . . . . C22 C 0.1059(6) 0.28282(8) 0.35544(6) 0.0330 1.0000 Uani . . . . . . . C23 C -0.0086(6) 0.28309(9) 0.32542(8) 0.0440 1.0000 Uani . . . . . . . C24 C 0.0937(8) 0.26396(9) 0.29840(7) 0.0501 1.0000 Uani . . . . . . . C25 C 0.3049(7) 0.24436(9) 0.30140(7) 0.0470 1.0000 Uani . . . . . . . C26 C 0.4151(5) 0.24353(8) 0.33194(7) 0.0323 1.0000 Uani . . . . . . . H21 H 0.9663 0.3160 0.4364 0.0349(17) 1.0000 Uiso . . . . . . . H31 H 0.9792 0.3147 0.4990 0.0349(17) 1.0000 Uiso . . . . . . . H41 H 0.5895 0.2933 0.5199 0.0349(17) 1.0000 Uiso . . . . . . . H51 H 0.3298 0.2808 0.4707 0.0349(17) 1.0000 Uiso . . . . . . . H71 H 0.1691 0.3789 0.4679 0.0349(17) 1.0000 Uiso . . . . . . . H81 H 0.4231 0.4019 0.5154 0.0349(17) 1.0000 Uiso . . . . . . . H91 H 0.8106 0.4210 0.4928 0.0349(17) 1.0000 Uiso . . . . . . . H101 H 0.8038 0.4097 0.4308 0.0349(17) 1.0000 Uiso . . . . . . . H121 H 0.6901 0.3490 0.3887 0.0349(17) 1.0000 Uiso . . . . . . . H122 H 0.4902 0.3354 0.3661 0.0349(17) 1.0000 Uiso . . . . . . . H131 H 0.3908 0.3987 0.3884 0.0349(17) 1.0000 Uiso . . . . . . . H132 H 0.2324 0.3652 0.4041 0.0349(17) 1.0000 Uiso . . . . . . . H161 H 0.1329 0.1991 0.3930 0.0349(17) 1.0000 Uiso . . . . . . . H171 H 0.1553 0.1318 0.4168 0.0349(17) 1.0000 Uiso . . . . . . . H181 H 0.4812 0.1109 0.4451 0.0349(17) 1.0000 Uiso . . . . . . . H191 H 0.7915 0.1571 0.4496 0.0349(17) 1.0000 Uiso . . . . . . . H201 H 0.7727 0.2243 0.4263 0.0349(17) 1.0000 Uiso . . . . . . . H221 H 0.0374 0.2962 0.3739 0.0349(17) 1.0000 Uiso . . . . . . . H231 H -0.1538 0.2962 0.3234 0.0349(17) 1.0000 Uiso . . . . . . . H241 H 0.0183 0.2644 0.2778 0.0349(17) 1.0000 Uiso . . . . . . . H251 H 0.3741 0.2315 0.2828 0.0349(17) 1.0000 Uiso . . . . . . . H261 H 0.5571 0.2294 0.3342 0.0349(17) 1.0000 Uiso . . . . . . . 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 0.02667(19) 0.01689(14) 0.01938(14) -0.00024(15) -0.00218(17) -0.00042(17) C1 0.0241(14) 0.0155(10) 0.0206(11) -0.0011(9) -0.0016(13) -0.0017(12) C2 0.0235(14) 0.0231(12) 0.0225(11) -0.0010(9) 0.0001(13) -0.0001(13) C3 0.0309(16) 0.0258(12) 0.0234(12) -0.0032(10) -0.0088(14) 0.0068(14) C4 0.0393(18) 0.0176(11) 0.0211(12) 0.0017(9) 0.0010(14) 0.0045(14) C5 0.0262(15) 0.0159(12) 0.0253(13) 0.0021(10) -0.0002(12) -0.0019(11) C6 0.0326(17) 0.0161(12) 0.0279(13) 0.0038(10) -0.0042(12) 0.0028(11) C7 0.0258(17) 0.0205(12) 0.0398(15) 0.0018(10) 0.0028(14) 0.0040(12) C8 0.047(2) 0.0198(13) 0.0284(14) -0.0049(11) 0.0014(14) 0.0041(14) C9 0.0369(19) 0.0181(12) 0.0330(15) -0.0044(11) -0.0050(13) -0.0046(12) C10 0.0360(19) 0.0161(12) 0.0302(14) 0.0035(11) -0.0002(13) -0.0042(11) C11 0.0236(14) 0.0228(12) 0.0202(12) 0.0008(10) -0.0019(11) -0.0014(11) C12 0.0346(18) 0.0270(13) 0.0190(12) 0.0017(10) -0.0049(11) -0.0040(12) C13 0.0352(18) 0.0210(12) 0.0305(13) 0.0041(10) -0.0091(14) 0.0002(13) C14 0.0235(15) 0.0219(12) 0.0206(12) -0.0032(10) 0.0010(11) 0.0014(11) C15 0.0271(15) 0.0216(12) 0.0169(11) -0.0046(10) 0.0019(11) 0.0017(11) C16 0.0263(16) 0.0274(13) 0.0274(14) -0.0038(11) -0.0002(12) -0.0011(12) C17 0.0391(19) 0.0267(14) 0.0337(15) -0.0035(12) 0.0073(14) -0.0101(13) C18 0.054(2) 0.0208(13) 0.0241(14) 0.0006(11) 0.0062(14) -0.0018(14) C19 0.042(2) 0.0255(13) 0.0257(13) -0.0025(11) -0.0033(13) 0.0055(13) C20 0.0285(18) 0.0243(13) 0.0248(12) -0.0057(10) -0.0024(12) 0.0008(12) C21 0.0339(19) 0.0194(12) 0.0218(12) -0.0010(10) -0.0043(12) -0.0055(12) C22 0.0364(17) 0.0310(13) 0.0315(13) -0.0033(11) -0.0066(16) -0.0008(16) C23 0.051(2) 0.0306(16) 0.0505(19) 0.0055(14) -0.0247(17) -0.0056(15) C24 0.092(3) 0.0277(15) 0.0305(15) 0.0036(12) -0.025(2) -0.021(2) C25 0.085(3) 0.0325(16) 0.0236(14) -0.0030(12) -0.0030(18) -0.0136(19) C26 0.039(2) 0.0278(14) 0.0301(14) -0.0013(11) 0.0015(13) -0.0047(13) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Fe1 . C1 . 2.032(2) yes Fe1 . C2 . 2.041(3) yes Fe1 . C3 . 2.073(3) yes Fe1 . C4 . 2.085(2) yes Fe1 . C5 . 2.065(2) yes Fe1 . C6 . 2.033(3) yes Fe1 . C7 . 2.060(3) yes Fe1 . C8 . 2.071(3) yes Fe1 . C9 . 2.071(3) yes Fe1 . C10 . 2.049(3) yes C1 . C2 . 1.442(4) yes C1 . C5 . 1.444(4) yes C1 . C11 . 1.504(3) yes C2 . C3 . 1.439(3) yes C2 . H21 . 0.951 no C3 . C4 . 1.420(5) yes C3 . H31 . 0.951 no C4 . C5 . 1.435(4) yes C4 . H41 . 0.951 no C5 . H51 . 0.951 no C6 . C7 . 1.440(4) yes C6 . C10 . 1.442(4) yes C6 . C13 . 1.515(4) yes C7 . C8 . 1.435(4) yes C7 . H71 . 0.950 no C8 . C9 . 1.413(4) yes C8 . H81 . 0.951 no C9 . C10 . 1.440(4) yes C9 . H91 . 0.950 no C10 . H101 . 0.951 no C11 . C12 . 1.535(3) yes C11 . C14 . 1.354(3) yes C12 . C13 . 1.552(4) yes C12 . H121 . 0.951 no C12 . H122 . 0.951 no C13 . H131 . 0.950 no C13 . H132 . 0.951 no C14 . C15 . 1.518(3) yes C14 . C21 . 1.507(3) yes C15 . C16 . 1.402(4) yes C15 . C20 . 1.406(4) yes C16 . C17 . 1.411(4) yes C16 . H161 . 0.950 no C17 . C18 . 1.382(4) yes C17 . H171 . 0.951 no C18 . C19 . 1.393(4) yes C18 . H181 . 0.950 no C19 . C20 . 1.403(4) yes C19 . H191 . 0.950 no C20 . H201 . 0.950 no C21 . C22 . 1.391(4) yes C21 . C26 . 1.404(4) yes C22 . C23 . 1.396(4) yes C22 . H221 . 0.952 no C23 . C24 . 1.395(5) yes C23 . H231 . 0.951 no C24 . C25 . 1.391(6) yes C24 . H241 . 0.951 no C25 . C26 . 1.403(4) yes C25 . H251 . 0.952 no C26 . H261 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . Fe1 . C2 . 41.46(12) yes C1 . Fe1 . C3 . 69.11(10) yes C2 . Fe1 . C3 . 40.94(9) yes C1 . Fe1 . C4 . 68.85(8) yes C2 . Fe1 . C4 . 68.35(10) yes C3 . Fe1 . C4 . 39.92(13) yes C1 . Fe1 . C5 . 41.27(10) yes C2 . Fe1 . C5 . 69.02(11) yes C3 . Fe1 . C5 . 68.05(12) yes C4 . Fe1 . C5 . 40.44(11) yes C1 . Fe1 . C6 . 98.73(10) yes C2 . Fe1 . C6 . 116.88(11) yes C3 . Fe1 . C6 . 156.41(11) yes C4 . Fe1 . C6 . 155.48(12) yes C5 . Fe1 . C6 . 116.63(11) yes C1 . Fe1 . C7 . 118.08(12) yes C2 . Fe1 . C7 . 154.28(11) yes C3 . Fe1 . C7 . 162.40(11) yes C4 . Fe1 . C7 . 125.02(12) yes C5 . Fe1 . C7 . 105.94(11) yes C1 . Fe1 . C8 . 157.60(12) yes C2 . Fe1 . C8 . 160.82(12) yes C3 . Fe1 . C8 . 128.78(11) yes C4 . Fe1 . C8 . 114.62(11) yes C5 . Fe1 . C8 . 126.42(12) yes C1 . Fe1 . C9 . 154.36(11) yes C2 . Fe1 . C9 . 122.74(12) yes C3 . Fe1 . C9 . 113.00(11) yes C4 . Fe1 . C9 . 130.28(11) yes C5 . Fe1 . C9 . 164.36(11) yes C1 . Fe1 . C10 . 115.44(10) yes C2 . Fe1 . C10 . 103.38(11) yes C3 . Fe1 . C10 . 124.39(13) yes C4 . Fe1 . C10 . 163.03(13) yes C5 . Fe1 . C10 . 152.24(11) yes C6 . Fe1 . C7 . 41.19(11) yes C6 . Fe1 . C8 . 68.98(11) yes C7 . Fe1 . C8 . 40.66(11) yes C6 . Fe1 . C9 . 69.15(11) yes C7 . Fe1 . C9 . 68.14(12) yes C8 . Fe1 . C9 . 39.90(12) yes C6 . Fe1 . C10 . 41.35(11) yes C7 . Fe1 . C10 . 68.82(11) yes C8 . Fe1 . C10 . 68.23(11) yes C9 . Fe1 . C10 . 40.90(10) yes Fe1 . C1 . C2 . 69.61(13) yes Fe1 . C1 . C5 . 70.57(13) yes C2 . C1 . C5 . 107.4(2) yes Fe1 . C1 . C11 . 121.74(17) yes C2 . C1 . C11 . 126.8(2) yes C5 . C1 . C11 . 125.7(3) yes C1 . C2 . Fe1 . 68.93(15) yes C1 . C2 . C3 . 107.8(3) yes Fe1 . C2 . C3 . 70.72(16) yes C1 . C2 . H21 . 126.1 no Fe1 . C2 . H21 . 126.1 no C3 . C2 . H21 . 126.1 no C2 . C3 . Fe1 . 68.33(16) yes C2 . C3 . C4 . 108.4(3) yes Fe1 . C3 . C4 . 70.50(16) yes C2 . C3 . H31 . 125.8 no Fe1 . C3 . H31 . 125.7 no C4 . C3 . H31 . 125.9 no Fe1 . C4 . C3 . 69.58(14) yes Fe1 . C4 . C5 . 69.00(13) yes C3 . C4 . C5 . 108.4(2) yes Fe1 . C4 . H41 . 125.7 no C3 . C4 . H41 . 125.7 no C5 . C4 . H41 . 125.9 no C1 . C5 . C4 . 108.0(3) yes C1 . C5 . Fe1 . 68.16(13) yes C4 . C5 . Fe1 . 70.55(14) yes C1 . C5 . H51 . 126.0 no C4 . C5 . H51 . 126.0 no Fe1 . C5 . H51 . 126.0 no Fe1 . C6 . C7 . 70.38(15) yes Fe1 . C6 . C10 . 69.92(16) yes C7 . C6 . C10 . 107.4(2) yes Fe1 . C6 . C13 . 121.43(17) yes C7 . C6 . C13 . 126.9(3) yes C10 . C6 . C13 . 125.5(3) yes C6 . C7 . Fe1 . 68.42(15) yes C6 . C7 . C8 . 107.9(3) yes Fe1 . C7 . C8 . 70.09(17) yes C6 . C7 . H71 . 126.1 no Fe1 . C7 . H71 . 126.0 no C8 . C7 . H71 . 126.1 no C7 . C8 . Fe1 . 69.25(15) yes C7 . C8 . C9 . 108.7(2) yes Fe1 . C8 . C9 . 70.05(17) yes C7 . C8 . H81 . 125.6 no Fe1 . C8 . H81 . 125.6 no C9 . C8 . H81 . 125.7 no C8 . C9 . Fe1 . 70.05(16) yes C8 . C9 . C10 . 108.2(2) yes Fe1 . C9 . C10 . 68.75(14) yes C8 . C9 . H91 . 125.8 no Fe1 . C9 . H91 . 125.8 no C10 . C9 . H91 . 125.9 no C6 . C10 . C9 . 107.9(2) yes C6 . C10 . Fe1 . 68.73(15) yes C9 . C10 . Fe1 . 70.35(14) yes C6 . C10 . H101 . 126.1 no C9 . C10 . H101 . 126.0 no Fe1 . C10 . H101 . 126.0 no C1 . C11 . C12 . 115.1(2) yes C1 . C11 . C14 . 122.2(2) yes C12 . C11 . C14 . 122.6(2) yes C11 . C12 . C13 . 115.5(2) yes C11 . C12 . H121 . 108.0 no C13 . C12 . H121 . 108.0 no C11 . C12 . H122 . 108.0 no C13 . C12 . H122 . 108.0 no H121 . C12 . H122 . 109.3 no C12 . C13 . C6 . 114.3(2) yes C12 . C13 . H131 . 108.3 no C6 . C13 . H131 . 108.3 no C12 . C13 . H132 . 108.2 no C6 . C13 . H132 . 108.2 no H131 . C13 . H132 . 109.4 no C11 . C14 . C15 . 123.0(2) yes C11 . C14 . C21 . 122.3(2) yes C15 . C14 . C21 . 114.6(2) yes C14 . C15 . C16 . 120.2(2) yes C14 . C15 . C20 . 121.4(2) yes C16 . C15 . C20 . 118.3(2) yes C15 . C16 . C17 . 120.2(3) yes C15 . C16 . H161 . 119.9 no C17 . C16 . H161 . 119.9 no C16 . C17 . C18 . 120.9(3) yes C16 . C17 . H171 . 119.6 no C18 . C17 . H171 . 119.6 no C17 . C18 . C19 . 119.5(2) yes C17 . C18 . H181 . 120.3 no C19 . C18 . H181 . 120.3 no C18 . C19 . C20 . 120.2(3) yes C18 . C19 . H191 . 119.8 no C20 . C19 . H191 . 119.9 no C15 . C20 . C19 . 120.9(3) yes C15 . C20 . H201 . 119.6 no C19 . C20 . H201 . 119.5 no C14 . C21 . C22 . 121.0(2) yes C14 . C21 . C26 . 120.5(3) yes C22 . C21 . C26 . 118.4(2) yes C21 . C22 . C23 . 121.9(3) yes C21 . C22 . H221 . 119.1 no C23 . C22 . H221 . 119.1 no C22 . C23 . C24 . 118.9(3) yes C22 . C23 . H231 . 120.6 no C24 . C23 . H231 . 120.5 no C23 . C24 . C25 . 120.6(3) yes C23 . C24 . H241 . 119.6 no C25 . C24 . H241 . 119.8 no C24 . C25 . C26 . 119.7(3) yes C24 . C25 . H251 . 120.1 no C26 . C25 . H251 . 120.2 no C21 . C26 . C25 . 120.5(3) yes C21 . C26 . H261 . 119.7 no C25 . C26 . H261 . 119.8 no data_compound_8 _database_code_depnum_ccdc_archive 'CCDC 768982' #TrackingRef '- gormen.cif' _audit_creation_date 10-02-22 _audit_creation_method CRYSTALS_ver_12.87 _oxford_structure_analysis_title '2031107 Compound X' _chemical_name_systematic ; 1-[(4-N-acetamidophenyl)-(4-hydroxyphenyl) -methylidenyl]-[3]ferrocenophane ; _chemical_melting_point ? _publ_section_exptl_refinement ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _cell_length_a 5.8841(7) _cell_length_b 19.872(2) _cell_length_c 11.1212(17) _cell_angle_alpha 90 _cell_angle_beta 95.141(10) _cell_angle_gamma 90 _cell_volume 1295.1(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Fe 0.3463 0.8444 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805 1.0369 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C28 H25 Fe1 N1 O2 # Dc = 1.19 Fooo = 528.00 Mu = 6.04 M = 463.36 # Found Formula = C30 H28 Fe1 N2 O2 # Dc = 1.29 FOOO = 528.00 Mu = 6.11 M = 504.41 _chemical_formula_sum 'C30 H28 Fe1 N2 O2' _chemical_formula_moiety 'C28 H25 Fe1 N O2, C2 H3 N' _chemical_compound_source ? _chemical_formula_weight 504.41 _cell_measurement_reflns_used 145 _cell_measurement_theta_min 2 _cell_measurement_theta_max 24 _cell_measurement_temperature 200 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_min 0.110 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_max 0.170 _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.611 # Sheldrick geometric approximatio 0.91 0.93 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.93 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 21914 _reflns_number_total 7479 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections without Friedels Law is 7479 # Number of reflections with Friedels Law is 3870 # Theoretical number of reflections is about 3780 _diffrn_reflns_theta_min 1.839 _diffrn_reflns_theta_max 30.007 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.007 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -27 _reflns_limit_k_max 27 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.59 _refine_diff_density_max 0.59 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 7476 _refine_ls_number_restraints 1 _refine_ls_number_parameters 326 _oxford_refine_ls_R_factor_ref 0.0591 _refine_ls_wR_factor_ref 0.0756 _refine_ls_goodness_of_fit_ref 0.9341 _refine_ls_shift/su_max 0.0027659 _refine_ls_shift/su_mean 0.0401075 # The values computed from all data _oxford_reflns_number_all 7478 _refine_ls_R_factor_all 0.0606 _refine_ls_wR_factor_all 0.1068 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5864 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_gt 0.0696 _refine_ls_abs_structure_Flack 0.043(19) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 0.57P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Sheldrick, G. M. (2008). Acta Cryst A64, 112-122. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Fe1 Fe 0.95090(4) 0.16980(5) 1.01274(2) 0.0232 1.0000 Uani . . . . . . . C1 C 0.9500(4) 0.27100(10) 0.98386(17) 0.0227 1.0000 Uani . . . . . . . C2 C 1.1781(4) 0.24409(11) 0.98120(19) 0.0248 1.0000 Uani . . . . . . . C3 C 1.1750(4) 0.19492(11) 0.8864(2) 0.0293 1.0000 Uani . . . . . . . C4 C 0.9472(4) 0.19116(11) 0.82947(19) 0.0297 1.0000 Uani . . . . . . . C5 C 0.8098(4) 0.23809(11) 0.88858(19) 0.0259 1.0000 Uani . . . . . . . C6 C 0.8276(3) 0.16883(15) 1.17810(16) 0.0291 1.0000 Uani . . . . . . . C7 C 0.6808(4) 0.12994(12) 1.0944(2) 0.0340 1.0000 Uani . . . . . . . C8 C 0.8140(5) 0.07653(11) 1.0483(2) 0.0383 1.0000 Uani . . . . . . . C9 C 1.0405(4) 0.08138(11) 1.1050(2) 0.0352 1.0000 Uani . . . . . . . C10 C 1.0498(4) 0.13792(12) 1.1848(2) 0.0325 1.0000 Uani . . . . . . . C11 C 0.8670(3) 0.31876(10) 1.07516(18) 0.0216 1.0000 Uani . . . . . . . C12 C 0.9069(4) 0.29658(11) 1.20682(19) 0.0288 1.0000 Uani . . . . . . . C13 C 0.7652(4) 0.23399(12) 1.2406(2) 0.0329 1.0000 Uani . . . . . . . C14 C 0.7593(3) 0.37701(10) 1.04084(18) 0.0222 1.0000 Uani . . . . . . . C15 C 0.6461(4) 0.42043(11) 1.13001(17) 0.0232 1.0000 Uani . . . . . . . C16 C 0.4480(4) 0.39932(12) 1.1786(2) 0.0326 1.0000 Uani . . . . . . . C17 C 0.3332(4) 0.43900(12) 1.2587(2) 0.0344 1.0000 Uani . . . . . . . C18 C 0.4214(4) 0.50211(11) 1.29159(18) 0.0249 1.0000 Uani . . . . . . . C19 C 0.6177(4) 0.52481(11) 1.24264(19) 0.0294 1.0000 Uani . . . . . . . C20 C 0.7287(4) 0.48491(11) 1.16212(19) 0.0268 1.0000 Uani . . . . . . . C21 C 0.7387(3) 0.40336(10) 0.91386(17) 0.0213 1.0000 Uani . . . . . . . C22 C 0.5405(4) 0.43709(12) 0.8680(2) 0.0261 1.0000 Uani . . . . . . . C23 C 0.5155(4) 0.46258(13) 0.7506(2) 0.0318 1.0000 Uani . . . . . . . C24 C 0.6917(4) 0.45562(12) 0.67537(19) 0.0313 1.0000 Uani . . . . . . . C25 C 0.8935(4) 0.42301(12) 0.72025(19) 0.0306 1.0000 Uani . . . . . . . C26 C 0.9160(4) 0.39782(11) 0.83758(19) 0.0269 1.0000 Uani . . . . . . . C27 C 0.1560(4) 0.53127(13) 1.44804(19) 0.0353 1.0000 Uani . . . . . . . C28 C 0.1010(6) 0.58907(15) 1.5310(3) 0.0572 1.0000 Uani . . . . . . . C30 C 0.5972(7) 0.74030(18) 0.4200(4) 0.0785 1.0000 Uani . . . . . . . C31 C 0.637(3) 0.8151(5) 0.4593(14) 0.1389 0.5000 Uani . . . . . . . C32 C 0.684(3) 0.8037(5) 0.3848(11) 0.1254 0.5000 Uani . . . . . . . O1 O 0.6576(3) 0.47974(12) 0.55986(15) 0.0544 1.0000 Uani . . . . . . . O2 O 0.0561(3) 0.47653(10) 1.44973(15) 0.0433 1.0000 Uani . . . . . . . N1 N 0.3187(3) 0.54621(10) 1.37255(16) 0.0305 1.0000 Uani . . . . . . . N2 N 0.5475(6) 0.68709(13) 0.4183(3) 0.0799 1.0000 Uani . . . . . . . H2 H 0.7844 0.4829 0.5328 0.0439(14) 1.0000 Uiso . . . . . . . H11 H 0.3818 0.5862 1.3807 0.0439(14) 1.0000 Uiso . . . . . . . H21 H 1.3083 0.2556 1.0316 0.0439(14) 1.0000 Uiso . . . . . . . H31 H 1.3064 0.1685 0.8669 0.0439(14) 1.0000 Uiso . . . . . . . H41 H 0.8961 0.1626 0.7614 0.0439(14) 1.0000 Uiso . . . . . . . H51 H 0.6503 0.2442 0.8700 0.0439(14) 1.0000 Uiso . . . . . . . H71 H 0.5209 0.1379 1.0743 0.0439(14) 1.0000 Uiso . . . . . . . H81 H 0.7576 0.0403 0.9896 0.0439(14) 1.0000 Uiso . . . . . . . H91 H 1.1667 0.0502 1.0923 0.0439(14) 1.0000 Uiso . . . . . . . H101 H 1.1835 0.1521 1.2355 0.0439(14) 1.0000 Uiso . . . . . . . H121 H 0.8778 0.3335 1.2578 0.0439(14) 1.0000 Uiso . . . . . . . H122 H 1.0677 0.2859 1.2251 0.0439(14) 1.0000 Uiso . . . . . . . H131 H 0.6050 0.2424 1.2183 0.0439(14) 1.0000 Uiso . . . . . . . H132 H 0.7898 0.2271 1.3266 0.0439(14) 1.0000 Uiso . . . . . . . H161 H 0.3842 0.3565 1.1565 0.0439(14) 1.0000 Uiso . . . . . . . H171 H 0.1997 0.4239 1.2873 0.0439(14) 1.0000 Uiso . . . . . . . H191 H 0.6789 0.5681 1.2666 0.0439(14) 1.0000 Uiso . . . . . . . H201 H 0.8576 0.5022 1.1301 0.0439(14) 1.0000 Uiso . . . . . . . H221 H 0.4190 0.4425 0.9187 0.0439(14) 1.0000 Uiso . . . . . . . H231 H 0.3821 0.4821 0.7227 0.0439(14) 1.0000 Uiso . . . . . . . H251 H 1.0152 0.4194 0.6720 0.0439(14) 1.0000 Uiso . . . . . . . H261 H 1.0527 0.3743 0.8665 0.0439(14) 1.0000 Uiso . . . . . . . H281 H 0.1880 0.6276 1.5158 0.0439(14) 1.0000 Uiso . . . . . . . H282 H 0.1227 0.5763 1.6139 0.0439(14) 1.0000 Uiso . . . . . . . H283 H -0.0565 0.6018 1.5141 0.0439(14) 1.0000 Uiso . . . . . . . H312 H 0.7266 0.8345 0.5225 0.0439(14) 0.5000 Uiso . . . . . . . H314 H 0.5306 0.8508 0.4614 0.0439(14) 0.5000 Uiso . . . . . . . H321 H 0.6260 0.8505 0.3907 0.0439(14) 0.5000 Uiso . . . . . . . H323 H 0.6664 0.8271 0.3141 0.0439(14) 0.5000 Uiso . . . . . . . H324 H 0.8528 0.8133 0.3734 0.0439(14) 0.5000 Uiso . . . . . . . H3211 H 0.7847 0.8387 0.4435 0.0439(14) 0.5000 Uiso . . . . . . . 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 0.02532(14) 0.01704(11) 0.02815(14) 0.00225(14) 0.00727(10) 0.00062(16) C1 0.0262(11) 0.0180(9) 0.0248(10) 0.0034(7) 0.0061(9) 0.0017(8) C2 0.0241(11) 0.0215(9) 0.0295(11) -0.0001(8) 0.0065(9) -0.0032(8) C3 0.0345(13) 0.0238(9) 0.0315(11) -0.0006(8) 0.0135(10) 0.0026(9) C4 0.0386(13) 0.0252(10) 0.0255(10) -0.0034(8) 0.0047(10) -0.0023(9) C5 0.0287(11) 0.0236(10) 0.0253(11) 0.0038(8) 0.0017(9) -0.0006(8) C6 0.0341(10) 0.0256(8) 0.0294(9) 0.0121(12) 0.0136(8) 0.0037(14) C7 0.0290(12) 0.0276(11) 0.0468(14) 0.0109(10) 0.0116(11) -0.0035(9) C8 0.0462(16) 0.0194(10) 0.0502(15) 0.0059(10) 0.0098(12) -0.0069(10) C9 0.0410(14) 0.0222(10) 0.0443(14) 0.0111(10) 0.0135(11) 0.0096(10) C10 0.0365(13) 0.0293(11) 0.0321(11) 0.0121(9) 0.0055(10) 0.0039(10) C11 0.0211(10) 0.0213(9) 0.0235(10) -0.0011(8) 0.0073(8) -0.0017(8) C12 0.0344(13) 0.0285(11) 0.0236(10) 0.0007(8) 0.0040(9) 0.0037(9) C13 0.0391(13) 0.0346(12) 0.0271(11) 0.0087(9) 0.0139(10) 0.0050(10) C14 0.0209(10) 0.0202(9) 0.0263(10) -0.0011(8) 0.0070(8) -0.0018(8) C15 0.0286(12) 0.0204(9) 0.0214(10) 0.0008(8) 0.0064(9) 0.0021(8) C16 0.0340(14) 0.0240(11) 0.0420(14) -0.0101(10) 0.0156(11) -0.0054(10) C17 0.0350(13) 0.0301(11) 0.0405(13) -0.0077(10) 0.0170(11) -0.0042(10) C18 0.0318(12) 0.0233(10) 0.0198(10) -0.0001(8) 0.0040(9) 0.0074(9) C19 0.0415(13) 0.0196(10) 0.0275(11) -0.0022(8) 0.0050(10) -0.0025(9) C20 0.0319(12) 0.0232(10) 0.0266(10) 0.0012(8) 0.0100(9) -0.0029(9) C21 0.0243(11) 0.0159(9) 0.0247(10) -0.0010(7) 0.0074(8) -0.0016(8) C22 0.0250(12) 0.0280(11) 0.0265(11) -0.0033(9) 0.0086(9) 0.0020(10) C23 0.0219(12) 0.0411(13) 0.0321(11) 0.0018(10) 0.0001(10) 0.0047(9) C24 0.0288(12) 0.0408(12) 0.0243(10) 0.0022(9) 0.0021(9) -0.0013(10) C25 0.0296(13) 0.0335(11) 0.0305(11) 0.0019(9) 0.0130(10) 0.0020(9) C26 0.0251(11) 0.0232(10) 0.0336(11) 0.0055(9) 0.0091(9) 0.0038(9) C27 0.0447(14) 0.0423(13) 0.0193(10) -0.0028(9) 0.0058(10) 0.0155(11) C28 0.079(2) 0.0535(17) 0.0422(15) -0.0149(13) 0.0231(15) 0.0135(16) C30 0.085(3) 0.0479(18) 0.102(3) 0.0182(19) 0.003(2) -0.0091(18) C31 0.176(14) 0.041(5) 0.187(14) -0.004(7) -0.057(12) -0.017(6) C32 0.221(14) 0.040(5) 0.125(10) -0.008(5) 0.071(10) -0.046(6) O1 0.0386(11) 0.0928(16) 0.0329(9) 0.0208(10) 0.0087(8) 0.0118(10) O2 0.0536(12) 0.0460(10) 0.0337(8) -0.0054(8) 0.0222(8) -0.0022(9) N1 0.0421(11) 0.0254(9) 0.0249(9) -0.0036(7) 0.0075(8) 0.0058(8) N2 0.098(2) 0.050(2) 0.094(2) -0.0074(15) 0.0171(18) -0.0109(14) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.8934(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Fe1 . C1 . 2.0363(19) yes Fe1 . C2 . 2.043(2) yes Fe1 . C3 . 2.072(2) yes Fe1 . C4 . 2.080(2) yes Fe1 . C5 . 2.057(2) yes Fe1 . C6 . 2.0368(17) yes Fe1 . C7 . 2.059(2) yes Fe1 . C8 . 2.073(2) yes Fe1 . C9 . 2.079(2) yes Fe1 . C10 . 2.050(2) yes C1 . C2 . 1.447(3) yes C1 . C5 . 1.440(3) yes C1 . C11 . 1.503(3) yes C2 . C3 . 1.436(3) yes C2 . H21 . 0.936 no C3 . C4 . 1.432(3) yes C3 . H31 . 0.975 no C4 . C5 . 1.432(3) yes C4 . H41 . 0.972 no C5 . H51 . 0.951 no C6 . C7 . 1.437(3) yes C6 . C10 . 1.441(3) yes C6 . C13 . 1.530(3) yes C7 . C8 . 1.441(3) yes C7 . H71 . 0.960 no C8 . C9 . 1.426(4) yes C8 . H81 . 1.008 no C9 . C10 . 1.430(3) yes C9 . H91 . 0.986 no C10 . H101 . 0.967 no C11 . C12 . 1.527(3) yes C11 . C14 . 1.358(3) yes C12 . C13 . 1.562(3) yes C12 . H121 . 0.952 no C12 . H122 . 0.973 no C13 . H131 . 0.968 no C13 . H132 . 0.964 no C14 . C15 . 1.513(3) yes C14 . C21 . 1.501(3) yes C15 . C16 . 1.392(3) yes C15 . C20 . 1.405(3) yes C16 . C17 . 1.407(3) yes C16 . H161 . 0.954 no C17 . C18 . 1.394(3) yes C17 . H171 . 0.924 no C18 . C19 . 1.395(3) yes C18 . N1 . 1.429(3) yes C19 . C20 . 1.401(3) yes C19 . H191 . 0.961 no C20 . H201 . 0.932 no C21 . C22 . 1.401(3) yes C21 . C26 . 1.407(3) yes C22 . C23 . 1.396(3) yes C22 . H221 . 0.955 no C23 . C24 . 1.396(3) yes C23 . H231 . 0.905 no C24 . C25 . 1.404(3) yes C24 . O1 . 1.369(3) yes C25 . C26 . 1.393(3) yes C25 . H251 . 0.936 no C26 . H261 . 0.961 no C27 . C28 . 1.526(3) yes C27 . O2 . 1.237(3) yes C27 . N1 . 1.361(3) yes C28 . H281 . 0.945 no C28 . H282 . 0.954 no C28 . H283 . 0.962 no C30 . C31 . 1.561(11) yes C30 . C32 . 1.426(10) yes C30 . N2 . 1.097(4) yes C31 . C32 . 0.924(17) yes C31 . H312 . 0.924 no C31 . H314 . 0.948 no C31 . H321 . 1.035 no C31 . H3211 . 1.015 no C32 . H321 . 0.996 no C32 . H323 . 0.912 no C32 . H324 . 1.032 no C32 . H3211 . 1.093 no O1 . H2 . 0.832 no N1 . H11 . 0.879 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . Fe1 . C2 . 41.56(8) yes C1 . Fe1 . C3 . 69.39(8) yes C2 . Fe1 . C3 . 40.85(8) yes C1 . Fe1 . C4 . 69.17(8) yes C2 . Fe1 . C4 . 68.53(8) yes C3 . Fe1 . C4 . 40.36(9) yes C1 . Fe1 . C5 . 41.20(8) yes C2 . Fe1 . C5 . 68.84(9) yes C3 . Fe1 . C5 . 68.23(9) yes C4 . Fe1 . C5 . 40.50(8) yes C1 . Fe1 . C6 . 98.96(10) yes C2 . Fe1 . C6 . 116.97(10) yes C3 . Fe1 . C6 . 156.12(9) yes C4 . Fe1 . C6 . 155.97(9) yes C5 . Fe1 . C6 . 117.21(9) yes C1 . Fe1 . C7 . 117.28(9) yes C2 . Fe1 . C7 . 153.74(9) yes C3 . Fe1 . C7 . 162.81(9) yes C4 . Fe1 . C7 . 124.76(10) yes C5 . Fe1 . C7 . 105.60(9) yes C1 . Fe1 . C8 . 156.56(9) yes C2 . Fe1 . C8 . 161.85(9) yes C3 . Fe1 . C8 . 128.79(9) yes C4 . Fe1 . C8 . 113.53(9) yes C5 . Fe1 . C8 . 125.27(10) yes C1 . Fe1 . C9 . 155.44(9) yes C2 . Fe1 . C9 . 123.69(9) yes C3 . Fe1 . C9 . 112.92(9) yes C4 . Fe1 . C9 . 129.49(9) yes C5 . Fe1 . C9 . 163.36(9) yes C1 . Fe1 . C10 . 116.67(9) yes C2 . Fe1 . C10 . 104.37(9) yes C3 . Fe1 . C10 . 124.24(9) yes C4 . Fe1 . C10 . 162.73(9) yes C5 . Fe1 . C10 . 153.40(9) yes C6 . Fe1 . C7 . 41.08(10) yes C6 . Fe1 . C8 . 69.10(11) yes C7 . Fe1 . C8 . 40.8(1) yes C6 . Fe1 . C9 . 69.00(10) yes C7 . Fe1 . C9 . 68.20(9) yes C8 . Fe1 . C9 . 40.16(10) yes C6 . Fe1 . C10 . 41.28(9) yes C7 . Fe1 . C10 . 68.59(10) yes C8 . Fe1 . C10 . 68.18(10) yes C9 . Fe1 . C10 . 40.53(9) yes Fe1 . C1 . C2 . 69.46(11) yes Fe1 . C1 . C5 . 70.18(11) yes C2 . C1 . C5 . 106.76(17) yes Fe1 . C1 . C11 . 120.89(13) yes C2 . C1 . C11 . 127.25(19) yes C5 . C1 . C11 . 125.73(19) yes C1 . C2 . Fe1 . 68.97(11) yes C1 . C2 . C3 . 108.39(19) yes Fe1 . C2 . C3 . 70.66(12) yes C1 . C2 . H21 . 127.5 no Fe1 . C2 . H21 . 125.9 no C3 . C2 . H21 . 124.1 no C2 . C3 . Fe1 . 68.49(11) yes C2 . C3 . C4 . 108.05(18) yes Fe1 . C3 . C4 . 70.12(13) yes C2 . C3 . H31 . 124.9 no Fe1 . C3 . H31 . 125.9 no C4 . C3 . H31 . 127.1 no C3 . C4 . Fe1 . 69.52(12) yes C3 . C4 . C5 . 107.91(18) yes Fe1 . C4 . C5 . 68.90(12) yes C3 . C4 . H41 . 125.9 no Fe1 . C4 . H41 . 128.3 no C5 . C4 . H41 . 126.1 no C1 . C5 . C4 . 108.87(19) yes C1 . C5 . Fe1 . 68.62(11) yes C4 . C5 . Fe1 . 70.61(12) yes C1 . C5 . H51 . 126.3 no C4 . C5 . H51 . 124.8 no Fe1 . C5 . H51 . 124.2 no Fe1 . C6 . C7 . 70.29(12) yes Fe1 . C6 . C10 . 69.86(11) yes C7 . C6 . C10 . 107.1(2) yes Fe1 . C6 . C13 . 121.46(16) yes C7 . C6 . C13 . 126.49(19) yes C10 . C6 . C13 . 126.2(2) yes C6 . C7 . Fe1 . 68.64(11) yes C6 . C7 . C8 . 108.2(2) yes Fe1 . C7 . C8 . 70.12(13) yes C6 . C7 . H71 . 125.6 no Fe1 . C7 . H71 . 127.8 no C8 . C7 . H71 . 126.2 no C7 . C8 . Fe1 . 69.06(12) yes C7 . C8 . C9 . 108.0(2) yes Fe1 . C8 . C9 . 70.13(12) yes C7 . C8 . H81 . 126.8 no Fe1 . C8 . H81 . 128.8 no C9 . C8 . H81 . 125.1 no C8 . C9 . Fe1 . 69.71(12) yes C8 . C9 . C10 . 108.1(2) yes Fe1 . C9 . C10 . 68.67(12) yes C8 . C9 . H91 . 125.5 no Fe1 . C9 . H91 . 128.4 no C10 . C9 . H91 . 126.4 no C6 . C10 . C9 . 108.6(2) yes C6 . C10 . Fe1 . 68.86(11) yes C9 . C10 . Fe1 . 70.81(13) yes C6 . C10 . H101 . 126.4 no C9 . C10 . H101 . 125.0 no Fe1 . C10 . H101 . 127.0 no C1 . C11 . C12 . 115.73(17) yes C1 . C11 . C14 . 121.34(18) yes C12 . C11 . C14 . 122.91(17) yes C11 . C12 . C13 . 114.91(18) yes C11 . C12 . H121 . 109.1 no C13 . C12 . H121 . 110.0 no C11 . C12 . H122 . 109.0 no C13 . C12 . H122 . 107.8 no H121 . C12 . H122 . 105.5 no C6 . C13 . C12 . 114.17(17) yes C6 . C13 . H131 . 107.3 no C12 . C13 . H131 . 109.2 no C6 . C13 . H132 . 108.0 no C12 . C13 . H132 . 108.5 no H131 . C13 . H132 . 109.6 no C11 . C14 . C15 . 121.58(18) yes C11 . C14 . C21 . 123.93(18) yes C15 . C14 . C21 . 114.49(16) yes C14 . C15 . C16 . 121.00(18) yes C14 . C15 . C20 . 121.60(19) yes C16 . C15 . C20 . 117.31(19) yes C15 . C16 . C17 . 122.9(2) yes C15 . C16 . H161 . 119.5 no C17 . C16 . H161 . 117.6 no C16 . C17 . C18 . 118.8(2) yes C16 . C17 . H171 . 120.5 no C18 . C17 . H171 . 120.7 no C17 . C18 . C19 . 119.36(19) yes C17 . C18 . N1 . 123.3(2) yes C19 . C18 . N1 . 117.36(18) yes C18 . C19 . C20 . 121.08(19) yes C18 . C19 . H191 . 118.9 no C20 . C19 . H191 . 120.0 no C15 . C20 . C19 . 120.53(19) yes C15 . C20 . H201 . 120.9 no C19 . C20 . H201 . 118.6 no C14 . C21 . C22 . 120.24(18) yes C14 . C21 . C26 . 122.59(18) yes C22 . C21 . C26 . 117.14(18) yes C21 . C22 . C23 . 121.9(2) yes C21 . C22 . H221 . 118.8 no C23 . C22 . H221 . 119.3 no C22 . C23 . C24 . 120.2(2) yes C22 . C23 . H231 . 119.4 no C24 . C23 . H231 . 120.3 no C23 . C24 . C25 . 118.8(2) yes C23 . C24 . O1 . 118.2(2) yes C25 . C24 . O1 . 122.9(2) yes C24 . C25 . C26 . 120.3(2) yes C24 . C25 . H251 . 119.8 no C26 . C25 . H251 . 119.8 no C21 . C26 . C25 . 121.6(2) yes C21 . C26 . H261 . 118.7 no C25 . C26 . H261 . 119.7 no C28 . C27 . O2 . 121.7(2) yes C28 . C27 . N1 . 114.1(2) yes O2 . C27 . N1 . 124.21(19) yes C27 . C28 . H281 . 110.7 no C27 . C28 . H282 . 111.5 no H281 . C28 . H282 . 111.1 no C27 . C28 . H283 . 109.4 no H281 . C28 . H283 . 106.3 no H282 . C28 . H283 . 107.5 no C31 . C30 . C32 . 35.7(6) yes C31 . C30 . N2 . 163.0(8) yes C32 . C30 . N2 . 161.4(6) yes C30 . C31 . C32 . 64.2(10) yes C30 . C31 . H312 . 132.2 no C32 . C31 . H312 . 126.2 no C30 . C31 . H314 . 129.4 no C32 . C31 . H314 . 117.2 no H312 . C31 . H314 . 90.1 no C30 . C31 . H321 . 116.3 no C32 . C31 . H321 . 60.8 no H312 . C31 . H321 . 105.7 no H314 . C31 . H321 . 60.8 no C30 . C31 . H3211 . 120.1 no C32 . C31 . H3211 . 68.4 no H312 . C31 . H3211 . 60.1 no H314 . C31 . H3211 . 103.8 no H321 . C31 . H3211 . 63.8 no C30 . C32 . C31 . 80.2(12) yes C30 . C32 . H321 . 132.4 no C31 . C32 . H321 . 65.1 no C30 . C32 . H323 . 132.2 no C31 . C32 . H323 . 128.9 no H321 . C32 . H323 . 64.3 no C30 . C32 . H324 . 124.8 no C31 . C32 . H324 . 115.5 no H321 . C32 . H324 . 99.9 no H323 . C32 . H324 . 80.4 no C30 . C32 . H3211 . 125.9 no C31 . C32 . H3211 . 59.8 no H321 . C32 . H3211 . 62.3 no H323 . C32 . H3211 . 101.7 no H324 . C32 . H3211 . 58.4 no C24 . O1 . H2 . 107.8 no C18 . N1 . C27 . 127.98(18) yes C18 . N1 . H11 . 114.9 no C27 . N1 . H11 . 116.6 no C31 . H321 . C32 . 54.1 no C32 . H3211 . C31 . 51.8 no