# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_3a _database_code_depnum_ccdc_archive 'CCDC 825996' #TrackingRef 'pyrylium ferric chlorate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H17 Cl4 Fe O' _chemical_formula_weight 507.02 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'Pbcn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.949(2) _cell_length_b 17.190(3) _cell_length_c 12.099(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2277.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2600 _cell_measurement_theta_min 3.37 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1028 _exptl_absorpt_coefficient_mu 1.143 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 'Bruker SMART CCD area-detector' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 20725 _diffrn_reflns_av_R_equivalents 0.1030 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2600 _reflns_number_gt 1366 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0977P)^2^+1.3017P] 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 2600 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1538 _refine_ls_R_factor_gt 0.0765 _refine_ls_wR_factor_ref 0.2092 _refine_ls_wR_factor_gt 0.1697 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.0000 0.29017(5) 0.2500 0.0597(4) Uani 1 2 d S . . Cl2 Cl 0.12871(18) 0.21824(9) 0.15708(16) 0.1057(7) Uani 1 1 d . . . Cl1 Cl 0.10000(17) 0.36379(13) 0.36292(15) 0.1170(7) Uani 1 1 d . . . O1 O 1.0000 0.9807(3) 0.2500 0.0712(13) Uani 1 2 d S . . C3 C 1.0000 0.8217(5) 0.2500 0.0696(19) Uani 1 2 d S . . C2 C 0.9370(4) 0.8658(3) 0.1723(4) 0.0621(13) Uani 1 1 d . . . H2 H 0.8921 0.8394 0.1189 0.074 Uiso 1 1 calc R . . C1 C 0.9369(4) 0.9432(3) 0.1693(4) 0.0626(13) Uani 1 1 d . . . C10 C 1.0000 0.7378(5) 0.2500 0.0684(19) Uani 1 2 d S . . C4 C 0.8746(4) 0.9937(3) 0.0921(4) 0.0588(12) Uani 1 1 d . . . C9 C 0.8217(4) 0.9620(3) -0.0028(4) 0.0711(14) Uani 1 1 d . . . H9 H 0.8241 0.9086 -0.0148 0.085 Uiso 1 1 calc R . . C8 C 0.7647(5) 1.0112(4) -0.0801(5) 0.0858(18) Uani 1 1 d . . . H8 H 0.7285 0.9912 -0.1436 0.103 Uiso 1 1 calc R . . C5 C 0.8699(5) 1.0721(4) 0.1063(6) 0.0859(17) Uani 1 1 d . . . H5 H 0.9056 1.0936 0.1690 0.103 Uiso 1 1 calc R . . C13 C 1.0000 0.5761(6) 0.2500 0.091(2) Uani 1 2 d S . . H13 H 1.0000 0.5220 0.2500 0.109 Uiso 1 2 calc SR . . C7 C 0.7642(6) 1.0900(5) -0.0590(7) 0.099(2) Uani 1 1 d . . . H7 H 0.7276 1.1235 -0.1095 0.118 Uiso 1 1 calc R . . C11 C 0.9868(6) 0.6954(4) 0.1519(5) 0.0867(18) Uani 1 1 d . . . H11 H 0.9770 0.7217 0.0853 0.104 Uiso 1 1 calc R . . C6 C 0.8155(7) 1.1197(4) 0.0329(7) 0.107(2) Uani 1 1 d . . . H6 H 0.8134 1.1730 0.0457 0.128 Uiso 1 1 calc R . . C12 C 0.9882(6) 0.6153(4) 0.1530(6) 0.0954(19) Uani 1 1 d . . . H12 H 0.9810 0.5878 0.0871 0.114 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0671(7) 0.0522(6) 0.0597(6) 0.000 0.0008(5) 0.000 Cl2 0.1241(14) 0.0703(10) 0.1228(13) -0.0022(9) 0.0467(11) 0.0152(9) Cl1 0.1068(13) 0.1475(18) 0.0966(12) -0.0360(11) -0.0114(10) -0.0326(12) O1 0.061(3) 0.080(3) 0.072(3) 0.000 0.002(3) 0.000 C3 0.054(4) 0.095(5) 0.060(4) 0.000 0.007(4) 0.000 C2 0.058(3) 0.067(4) 0.061(3) -0.001(3) -0.002(2) 0.003(3) C1 0.043(2) 0.090(4) 0.054(3) -0.008(3) 0.000(2) 0.000(3) C10 0.063(4) 0.070(5) 0.071(5) 0.000 -0.002(4) 0.000 C4 0.051(3) 0.060(3) 0.066(3) -0.008(2) 0.007(2) -0.001(2) C9 0.065(3) 0.075(4) 0.073(3) -0.002(3) 0.006(3) -0.005(3) C8 0.062(3) 0.125(6) 0.070(3) 0.011(4) -0.003(3) -0.015(4) C5 0.079(4) 0.070(4) 0.109(4) -0.003(4) 0.000(3) 0.006(3) C13 0.090(6) 0.078(6) 0.104(7) 0.000 0.000(5) 0.000 C7 0.071(4) 0.107(6) 0.118(6) 0.042(5) 0.010(4) 0.019(4) C11 0.095(4) 0.104(5) 0.062(3) 0.000(3) -0.009(3) 0.000(4) C6 0.103(5) 0.078(5) 0.140(7) 0.001(5) 0.008(5) 0.008(4) C12 0.114(5) 0.082(4) 0.091(4) -0.012(3) 0.001(4) -0.002(4) _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 Cl1 2.1603(17) . ? Fe1 Cl1 2.1603(17) 3 ? Fe1 Cl2 2.1861(17) 3 ? Fe1 Cl2 2.1861(17) . ? O1 C1 1.359(5) . ? O1 C1 1.359(5) 3_755 ? C3 C2 1.390(7) 3_755 ? C3 C2 1.390(7) . ? C3 C10 1.443(11) . ? C2 C1 1.331(7) . ? C2 H2 0.9300 . ? C1 C4 1.446(7) . ? C10 C11 1.399(7) . ? C10 C11 1.399(7) 3_755 ? C4 C5 1.360(7) . ? C4 C9 1.395(7) . ? C9 C8 1.407(8) . ? C9 H9 0.9300 . ? C8 C7 1.379(10) . ? C8 H8 0.9300 . ? C5 C6 1.347(9) . ? C5 H5 0.9300 . ? C13 C12 1.359(8) 3_755 ? C13 C12 1.359(8) . ? C13 H13 0.9300 . ? C7 C6 1.346(10) . ? C7 H7 0.9300 . ? C11 C12 1.378(8) . ? C11 H11 0.9300 . ? C6 H6 0.9300 . ? C12 H12 0.9300 . ? 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 Cl1 Fe1 Cl1 108.29(13) . 3 ? Cl1 Fe1 Cl2 109.44(8) . 3 ? Cl1 Fe1 Cl2 109.26(8) 3 3 ? Cl1 Fe1 Cl2 109.26(8) . . ? Cl1 Fe1 Cl2 109.44(8) 3 . ? Cl2 Fe1 Cl2 111.11(10) 3 . ? C1 O1 C1 123.4(6) . 3_755 ? C2 C3 C2 114.0(7) 3_755 . ? C2 C3 C10 123.0(4) 3_755 . ? C2 C3 C10 123.0(4) . . ? C1 C2 C3 124.3(5) . . ? C1 C2 H2 117.8 . . ? C3 C2 H2 117.8 . . ? C2 C1 O1 117.0(5) . . ? C2 C1 C4 128.2(5) . . ? O1 C1 C4 114.8(5) . . ? C11 C10 C11 117.3(8) . 3_755 ? C11 C10 C3 121.3(4) . . ? C11 C10 C3 121.3(4) 3_755 . ? C5 C4 C9 118.4(5) . . ? C5 C4 C1 122.0(5) . . ? C9 C4 C1 119.5(5) . . ? C4 C9 C8 119.8(6) . . ? C4 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C7 C8 C9 118.0(6) . . ? C7 C8 H8 121.0 . . ? C9 C8 H8 121.0 . . ? C6 C5 C4 122.3(7) . . ? C6 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? C12 C13 C12 120.6(9) 3_755 . ? C12 C13 H13 119.7 3_755 . ? C12 C13 H13 119.7 . . ? C6 C7 C8 121.5(7) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C12 C11 C10 120.7(6) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C7 C6 C5 120.0(7) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C13 C12 C11 120.3(7) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.329 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.052 data_3b _database_code_depnum_ccdc_archive 'CCDC 825997' #TrackingRef 'pyrylium ferric chlorate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 Cl4 Fe O2' _chemical_formula_weight 537.04 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.319(6) _cell_length_b 18.375(7) _cell_length_c 19.555(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4786(3) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3818 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2184 _exptl_absorpt_coefficient_mu 1.096 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 'Bruker SMART CCD area-detector' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 19326 _diffrn_reflns_av_R_equivalents 0.0658 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3818 _reflns_number_gt 2394 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0449P)^2^+0.6517P] 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 0 _refine_ls_number_reflns 3818 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0819 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.06815(4) 0.79170(3) 0.35702(2) 0.04936(19) Uani 1 1 d . . . Cl2 Cl 0.12413(9) 0.69982(5) 0.41678(5) 0.0669(3) Uani 1 1 d . . . Cl3 Cl 0.10281(9) 0.89257(6) 0.41019(6) 0.0723(3) Uani 1 1 d . . . Cl4 Cl -0.09475(8) 0.77504(6) 0.34495(5) 0.0689(3) Uani 1 1 d . . . Cl1 Cl 0.13636(10) 0.79860(6) 0.25575(5) 0.0833(4) Uani 1 1 d . . . O1 O 0.12459(18) 0.37299(12) 0.45418(11) 0.0478(6) Uani 1 1 d . . . O2 O 0.1455(2) 0.60852(15) 0.08987(12) 0.0630(8) Uani 1 1 d . . . C5 C 0.1252(3) 0.33783(19) 0.39341(17) 0.0423(9) Uani 1 1 d . . . C1 C 0.1326(3) 0.44639(19) 0.45790(17) 0.0430(9) Uani 1 1 d . . . C3 C 0.1401(3) 0.4526(2) 0.33544(17) 0.0441(9) Uani 1 1 d . . . C12 C 0.1429(3) 0.49479(18) 0.27249(16) 0.0422(9) Uani 1 1 d . . . C4 C 0.1324(3) 0.3765(2) 0.33490(17) 0.0473(10) Uani 1 1 d . . . H4 H 0.1322 0.3520 0.2933 0.057 Uiso 1 1 calc R . . C18 C 0.1170(3) 0.25916(19) 0.40091(17) 0.0444(9) Uani 1 1 d . . . C2 C 0.1411(3) 0.48584(19) 0.40001(16) 0.0439(9) Uani 1 1 d . . . H2 H 0.1477 0.5361 0.4030 0.053 Uiso 1 1 calc R . . C6 C 0.1269(3) 0.47353(19) 0.52820(16) 0.0426(9) Uani 1 1 d . . . C15 C 0.1460(3) 0.5749(2) 0.15132(17) 0.0489(10) Uani 1 1 d . . . C8 C 0.0939(3) 0.4538(3) 0.64695(19) 0.0618(12) Uani 1 1 d . . . H8 H 0.0749 0.4228 0.6823 0.074 Uiso 1 1 calc R . . C14 C 0.1713(3) 0.6079(2) 0.21219(18) 0.0546(10) Uani 1 1 d . . . H14 H 0.1892 0.6568 0.2131 0.066 Uiso 1 1 calc R . . C9 C 0.1156(3) 0.5250(3) 0.6607(2) 0.0641(12) Uani 1 1 d . . . H9 H 0.1125 0.5421 0.7054 0.077 Uiso 1 1 calc R . . C23 C 0.1165(3) 0.2271(2) 0.4645(2) 0.0570(11) Uani 1 1 d . . . H23 H 0.1198 0.2561 0.5034 0.068 Uiso 1 1 calc R . . C13 C 0.1697(3) 0.5677(2) 0.27159(17) 0.0529(10) Uani 1 1 d . . . H13 H 0.1873 0.5902 0.3125 0.063 Uiso 1 1 calc R . . C16 C 0.1182(3) 0.5028(2) 0.15077(18) 0.0629(12) Uani 1 1 d . . . H16 H 0.0997 0.4806 0.1099 0.075 Uiso 1 1 calc R . . C19 C 0.1111(3) 0.2145(2) 0.3439(2) 0.0593(11) Uani 1 1 d . . . H19 H 0.1110 0.2350 0.3004 0.071 Uiso 1 1 calc R . . C20 C 0.1055(3) 0.1401(2) 0.3511(2) 0.0675(12) Uani 1 1 d . . . H20 H 0.1013 0.1108 0.3125 0.081 Uiso 1 1 calc R . . C17 C 0.1177(3) 0.4637(2) 0.21028(18) 0.0600(11) Uani 1 1 d . . . H17 H 0.0999 0.4148 0.2089 0.072 Uiso 1 1 calc R . . C24 C 0.1650(4) 0.6845(2) 0.0868(2) 0.0765(13) Uani 1 1 d . . . H24A H 0.1176 0.7099 0.1151 0.115 Uiso 1 1 calc R . . H24B H 0.1586 0.7010 0.0404 0.115 Uiso 1 1 calc R . . H24C H 0.2318 0.6940 0.1028 0.115 Uiso 1 1 calc R . . C10 C 0.1418(3) 0.5711(2) 0.6088(2) 0.0707(13) Uani 1 1 d . . . H10 H 0.1558 0.6197 0.6182 0.085 Uiso 1 1 calc R . . C7 C 0.0999(3) 0.4278(2) 0.58128(18) 0.0518(10) Uani 1 1 d . . . H7 H 0.0858 0.3792 0.5724 0.062 Uiso 1 1 calc R . . C21 C 0.1058(3) 0.1087(2) 0.4145(3) 0.0682(13) Uani 1 1 d . . . H21 H 0.1025 0.0584 0.4189 0.082 Uiso 1 1 calc R . . C22 C 0.1111(3) 0.1519(2) 0.4714(2) 0.0669(12) Uani 1 1 d . . . H22 H 0.1110 0.1310 0.5147 0.080 Uiso 1 1 calc R . . C11 C 0.1476(3) 0.5456(2) 0.54237(18) 0.0617(11) Uani 1 1 d . . . H11 H 0.1654 0.5771 0.5072 0.074 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0582(4) 0.0444(3) 0.0454(3) 0.0055(2) -0.0026(2) -0.0030(3) Cl2 0.0779(8) 0.0544(7) 0.0683(7) 0.0116(5) -0.0102(5) 0.0076(6) Cl3 0.0790(9) 0.0539(7) 0.0842(8) -0.0135(5) -0.0038(6) -0.0056(6) Cl4 0.0627(8) 0.0761(8) 0.0679(7) 0.0209(5) -0.0139(5) -0.0127(6) Cl1 0.1190(11) 0.0751(8) 0.0557(6) 0.0069(6) 0.0219(6) -0.0067(7) O1 0.0602(18) 0.0391(15) 0.0443(15) -0.0031(11) -0.0017(11) 0.0041(13) O2 0.074(2) 0.069(2) 0.0466(16) 0.0103(14) -0.0044(13) -0.0074(16) C5 0.039(2) 0.044(2) 0.044(2) -0.0028(18) 0.0005(16) 0.0024(18) C1 0.038(2) 0.042(2) 0.049(2) -0.0002(18) -0.0002(16) 0.0058(18) C3 0.040(2) 0.050(3) 0.043(2) -0.0022(17) -0.0032(16) 0.0052(19) C12 0.049(3) 0.039(2) 0.0386(19) -0.0027(16) -0.0003(16) 0.0019(18) C4 0.056(3) 0.047(2) 0.039(2) -0.0042(17) 0.0007(16) 0.004(2) C18 0.046(2) 0.038(2) 0.050(2) -0.0030(18) 0.0030(17) 0.0040(19) C2 0.048(3) 0.036(2) 0.047(2) -0.0050(17) -0.0040(17) 0.0003(18) C6 0.046(2) 0.042(2) 0.040(2) -0.0020(17) -0.0036(16) 0.0078(18) C15 0.047(3) 0.058(3) 0.041(2) 0.0046(19) 0.0005(17) 0.002(2) C8 0.062(3) 0.078(3) 0.045(2) 0.007(2) 0.0004(19) 0.006(2) C14 0.076(3) 0.043(2) 0.045(2) 0.0021(18) -0.0020(19) -0.002(2) C9 0.068(3) 0.077(3) 0.047(2) -0.015(2) -0.006(2) 0.012(3) C23 0.069(3) 0.050(3) 0.053(2) -0.0023(19) 0.004(2) 0.003(2) C13 0.066(3) 0.052(3) 0.040(2) -0.0078(18) -0.0015(18) -0.003(2) C16 0.084(3) 0.065(3) 0.040(2) -0.0036(19) -0.009(2) -0.015(3) C19 0.075(3) 0.050(3) 0.053(2) -0.003(2) 0.0016(19) 0.005(2) C20 0.080(4) 0.052(3) 0.071(3) -0.012(2) -0.003(2) 0.000(2) C17 0.085(3) 0.046(2) 0.049(2) -0.0045(19) -0.007(2) -0.008(2) C24 0.094(4) 0.073(3) 0.062(3) 0.019(2) -0.004(2) -0.012(3) C10 0.096(4) 0.054(3) 0.061(3) -0.014(2) -0.005(3) -0.002(2) C7 0.054(3) 0.055(2) 0.046(2) -0.0023(19) -0.0003(17) 0.007(2) C21 0.066(3) 0.042(3) 0.097(4) -0.003(3) 0.011(2) 0.001(2) C22 0.076(3) 0.053(3) 0.072(3) 0.009(2) 0.013(2) 0.003(2) C11 0.088(3) 0.053(3) 0.044(2) -0.0011(19) -0.005(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 Cl3 2.1748(13) . ? Fe1 Cl1 2.1826(14) . ? Fe1 Cl2 2.1844(12) . ? Fe1 Cl4 2.2039(15) . ? O1 C5 1.353(4) . ? O1 C1 1.355(4) . ? O2 C15 1.351(4) . ? O2 C24 1.422(4) . ? C5 C4 1.350(4) . ? C5 C18 1.457(5) . ? C1 C2 1.349(4) . ? C1 C6 1.464(4) . ? C3 C2 1.402(4) . ? C3 C4 1.404(4) . ? C3 C12 1.455(5) . ? C12 C17 1.385(5) . ? C12 C13 1.386(4) . ? C4 H4 0.9300 . ? C18 C23 1.376(5) . ? C18 C19 1.387(5) . ? C2 H2 0.9300 . ? C6 C11 1.382(5) . ? C6 C7 1.382(5) . ? C15 C16 1.376(5) . ? C15 C14 1.377(5) . ? C8 C9 1.366(5) . ? C8 C7 1.372(5) . ? C8 H8 0.9300 . ? C14 C13 1.377(5) . ? C14 H14 0.9300 . ? C9 C10 1.369(5) . ? C9 H9 0.9300 . ? C23 C22 1.390(5) . ? C23 H23 0.9300 . ? C13 H13 0.9300 . ? C16 C17 1.367(5) . ? C16 H16 0.9300 . ? C19 C20 1.377(5) . ? C19 H19 0.9300 . ? C20 C21 1.367(5) . ? C20 H20 0.9300 . ? C17 H17 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C10 C11 1.382(5) . ? C10 H10 0.9300 . ? C7 H7 0.9300 . ? C21 C22 1.368(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C11 H11 0.9300 . ? 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 Cl3 Fe1 Cl1 107.22(5) . . ? Cl3 Fe1 Cl2 109.30(5) . . ? Cl1 Fe1 Cl2 112.85(5) . . ? Cl3 Fe1 Cl4 112.25(5) . . ? Cl1 Fe1 Cl4 108.70(5) . . ? Cl2 Fe1 Cl4 106.62(5) . . ? C5 O1 C1 121.5(3) . . ? C15 O2 C24 119.1(3) . . ? C4 C5 O1 119.6(3) . . ? C4 C5 C18 127.7(3) . . ? O1 C5 C18 112.6(3) . . ? C2 C1 O1 119.8(3) . . ? C2 C1 C6 127.5(3) . . ? O1 C1 C6 112.7(3) . . ? C2 C3 C4 116.2(3) . . ? C2 C3 C12 122.0(3) . . ? C4 C3 C12 121.8(3) . . ? C17 C12 C13 116.7(3) . . ? C17 C12 C3 121.2(3) . . ? C13 C12 C3 122.1(3) . . ? C5 C4 C3 121.5(3) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C23 C18 C19 118.2(4) . . ? C23 C18 C5 121.1(3) . . ? C19 C18 C5 120.7(3) . . ? C1 C2 C3 121.4(3) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C11 C6 C7 118.9(3) . . ? C11 C6 C1 120.3(3) . . ? C7 C6 C1 120.8(3) . . ? O2 C15 C16 115.6(3) . . ? O2 C15 C14 124.7(4) . . ? C16 C15 C14 119.7(3) . . ? C9 C8 C7 120.3(4) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C13 C14 C15 119.3(3) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C8 C9 C10 120.0(4) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C18 C23 C22 120.9(4) . . ? C18 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C14 C13 C12 122.2(3) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C17 C16 C15 120.0(4) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C20 C19 C18 120.5(4) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 120.8(4) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C16 C17 C12 122.0(4) . . ? C16 C17 H17 119.0 . . ? C12 C17 H17 119.0 . . ? O2 C24 H24A 109.5 . . ? O2 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O2 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C9 C10 C11 120.1(4) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C8 C7 C6 120.4(4) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C20 C21 C22 119.5(4) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C21 C22 C23 120.0(4) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C6 C11 C10 120.1(4) . . ? C6 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.907 _refine_diff_density_max 0.267 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.052 data_3c _database_code_depnum_ccdc_archive 'CCDC 825998' #TrackingRef 'pyrylium ferric chlorate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H21 Cl4 Fe O3' _chemical_formula_weight 567.07 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/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 7.542(12) _cell_length_b 18.02(3) _cell_length_c 19.28(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.98(2) _cell_angle_gamma 90.00 _cell_volume 2601(7) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 5353 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 26.50 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1156 _exptl_absorpt_coefficient_mu 1.015 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 'Bruker SMART CCD area-detector' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 14003 _diffrn_reflns_av_R_equivalents 0.1139 _diffrn_reflns_av_sigmaI/netI 0.1826 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 26.50 _reflns_number_total 5353 _reflns_number_gt 1584 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0609P)^2^+0.0000P] 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 0 _refine_ls_number_reflns 5353 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2712 _refine_ls_R_factor_gt 0.0847 _refine_ls_wR_factor_ref 0.1981 _refine_ls_wR_factor_gt 0.1500 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.54080(17) 0.18369(5) 0.89099(5) 0.0914(5) Uani 1 1 d . . . Cl2 Cl 0.6171(3) 0.26627(10) 0.97314(10) 0.1157(8) Uani 1 1 d . . . Cl3 Cl 0.7660(4) 0.15469(11) 0.83685(14) 0.1512(12) Uani 1 1 d . . . Cl1 Cl 0.4422(5) 0.08371(11) 0.93408(15) 0.1994(17) Uani 1 1 d . . . Cl4 Cl 0.3339(5) 0.23772(18) 0.81962(16) 0.2041(15) Uani 1 1 d . . . O1 O 0.8520(7) 0.5729(3) 0.9030(3) 0.0900(15) Uani 1 1 d . . . C6 C 0.8635(10) 0.4574(4) 0.8482(4) 0.082(2) Uani 1 1 d . . . C3 C 0.7373(10) 0.5211(4) 1.0265(4) 0.075(2) Uani 1 1 d . . . O2 O 0.9992(8) 0.3326(3) 0.6823(3) 0.122(2) Uani 1 1 d . . . C1 C 0.8204(9) 0.5007(4) 0.9101(4) 0.075(2) Uani 1 1 d . . . C5 C 0.8253(10) 0.6217(4) 0.9552(4) 0.082(2) Uani 1 1 d . . . C11 C 0.8691(11) 0.3801(4) 0.8491(4) 0.099(3) Uani 1 1 d . . . H11 H 0.8437 0.3543 0.8885 0.119 Uiso 1 1 calc R . . C7 C 0.9027(10) 0.4944(4) 0.7899(4) 0.092(2) Uani 1 1 d . . . H7 H 0.8994 0.5460 0.7899 0.111 Uiso 1 1 calc R . . C9 C 0.9543(11) 0.3786(5) 0.7342(4) 0.092(2) Uani 1 1 d . . . C8 C 0.9484(11) 0.4571(4) 0.7293(4) 0.097(3) Uani 1 1 d . . . H8 H 0.9725 0.4824 0.6895 0.117 Uiso 1 1 calc R . . C17 C 0.6382(11) 0.5422(4) 1.1427(4) 0.097(3) Uani 1 1 d . . . H17 H 0.6416 0.5933 1.1362 0.117 Uiso 1 1 calc R . . C12 C 0.6826(11) 0.4912(5) 1.0910(4) 0.098(2) Uani 1 1 d . . . C2 C 0.7651(10) 0.4736(4) 0.9700(4) 0.088(2) Uani 1 1 d . . . H2 H 0.7451 0.4229 0.9738 0.106 Uiso 1 1 calc R . . C15 C 0.5821(13) 0.4367(6) 1.2173(5) 0.113(3) Uani 1 1 d . . . H15 H 0.5483 0.4186 1.2590 0.135 Uiso 1 1 calc R . . C4 C 0.7711(11) 0.5958(4) 1.0143(4) 0.095(2) Uani 1 1 d . . . H4 H 0.7549 0.6297 1.0494 0.113 Uiso 1 1 calc R . . C18 C 0.8711(10) 0.6971(4) 0.9345(5) 0.090(2) Uani 1 1 d . . . C10 C 0.9119(11) 0.3427(4) 0.7923(4) 0.102(3) Uani 1 1 d . . . H10 H 0.9123 0.2911 0.7930 0.122 Uiso 1 1 calc R . . O3 O 0.9936(9) 0.9104(4) 0.8723(3) 0.150(2) Uani 1 1 d . . . C22 C 0.9568(13) 0.7840(5) 0.8497(5) 0.137(4) Uani 1 1 d . . . H22 H 0.9853 0.7937 0.8050 0.164 Uiso 1 1 calc R . . C20 C 0.9148(14) 0.8261(5) 0.9652(6) 0.132(4) Uani 1 1 d . . . H20 H 0.9163 0.8647 0.9973 0.158 Uiso 1 1 calc R . . C14 C 0.6260(14) 0.3910(5) 1.1678(6) 0.144(4) Uani 1 1 d . . . H14 H 0.6239 0.3401 1.1756 0.173 Uiso 1 1 calc R . . C16 C 0.5884(13) 0.5102(8) 1.2048(5) 0.147(4) Uani 1 1 d . . . H16 H 0.5579 0.5423 1.2393 0.176 Uiso 1 1 calc R . . C23 C 0.9166(13) 0.7137(5) 0.8700(5) 0.122(3) Uani 1 1 d . . . H23 H 0.9206 0.6753 0.8380 0.147 Uiso 1 1 calc R . . C13 C 0.6753(11) 0.4171(4) 1.1044(4) 0.099(3) Uani 1 1 d . . . H13 H 0.7034 0.3834 1.0710 0.118 Uiso 1 1 calc R . . C21 C 0.9532(14) 0.8398(5) 0.8988(8) 0.140(4) Uani 1 1 d . . . C24 C 1.0467(14) 0.3630(6) 0.6227(5) 0.167(4) Uani 1 1 d . . . H24A H 1.1522 0.3926 0.6338 0.250 Uiso 1 1 calc R . . H24B H 0.9512 0.3936 0.6014 0.250 Uiso 1 1 calc R . . H24C H 1.0703 0.3242 0.5910 0.250 Uiso 1 1 calc R . . C19 C 0.8740(11) 0.7551(5) 0.9843(5) 0.119(3) Uani 1 1 d . . . H19 H 0.8486 0.7453 1.0295 0.143 Uiso 1 1 calc R . . C25 C 0.9988(17) 0.9673(6) 0.9189(6) 0.204(6) Uani 1 1 d . . . H25A H 1.0683 0.9528 0.9618 0.305 Uiso 1 1 calc R . . H25B H 0.8795 0.9792 0.9278 0.305 Uiso 1 1 calc R . . H25C H 1.0522 1.0100 0.9001 0.305 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.1229(11) 0.0690(6) 0.0860(8) -0.0110(6) 0.0273(7) -0.0030(7) Cl2 0.161(2) 0.0933(13) 0.0962(16) -0.0199(11) 0.0275(15) -0.0258(14) Cl3 0.181(3) 0.1000(14) 0.192(3) -0.0208(15) 0.099(2) 0.0095(16) Cl1 0.328(5) 0.0969(15) 0.203(3) -0.0349(17) 0.155(3) -0.069(2) Cl4 0.204(4) 0.235(3) 0.159(3) -0.021(2) -0.038(2) 0.050(3) O1 0.092(4) 0.079(3) 0.098(4) -0.008(3) 0.004(3) 0.012(3) C6 0.086(6) 0.093(5) 0.066(6) -0.002(5) 0.002(5) 0.006(5) C3 0.064(6) 0.099(5) 0.059(5) -0.006(5) -0.002(4) -0.001(4) O2 0.139(6) 0.144(5) 0.090(4) -0.023(4) 0.037(4) -0.011(4) C1 0.068(6) 0.086(5) 0.070(6) 0.015(4) 0.001(4) -0.009(4) C5 0.081(7) 0.082(5) 0.080(6) 0.001(5) 0.002(5) 0.007(5) C11 0.115(8) 0.094(5) 0.090(6) -0.002(5) 0.016(5) -0.003(5) C7 0.108(8) 0.078(5) 0.090(6) 0.002(5) 0.005(6) 0.006(5) C9 0.104(7) 0.112(6) 0.058(6) -0.018(5) 0.006(5) -0.005(5) C8 0.115(8) 0.098(6) 0.080(6) 0.003(5) 0.013(5) -0.002(5) C17 0.090(7) 0.121(6) 0.080(6) -0.027(5) 0.008(5) 0.015(5) C12 0.070(7) 0.131(7) 0.091(7) -0.002(6) 0.003(5) 0.011(6) C2 0.093(7) 0.087(5) 0.080(6) -0.012(5) -0.004(5) 0.002(4) C15 0.136(9) 0.132(7) 0.077(7) 0.003(6) 0.038(6) -0.002(7) C4 0.102(8) 0.093(6) 0.085(6) -0.004(5) 0.000(5) 0.013(5) C18 0.084(7) 0.085(5) 0.100(7) -0.017(5) 0.003(5) 0.010(5) C10 0.152(9) 0.085(5) 0.073(6) -0.019(5) 0.037(6) -0.001(5) O3 0.170(7) 0.112(5) 0.166(6) -0.018(4) 0.018(5) 0.005(4) C22 0.179(11) 0.077(6) 0.154(9) 0.007(7) 0.023(8) 0.009(6) C20 0.161(10) 0.070(6) 0.173(10) -0.010(6) 0.056(8) 0.000(6) C14 0.177(12) 0.144(8) 0.117(9) -0.001(7) 0.040(8) -0.013(7) C16 0.100(9) 0.246(13) 0.100(9) -0.032(9) 0.031(7) -0.006(9) C23 0.176(10) 0.092(6) 0.098(7) 0.002(5) 0.015(7) -0.001(6) C13 0.127(8) 0.094(6) 0.080(6) 0.002(5) 0.030(5) 0.002(5) C21 0.108(9) 0.079(7) 0.235(14) 0.037(8) 0.028(9) -0.003(6) C24 0.166(12) 0.218(11) 0.125(9) -0.025(8) 0.051(8) -0.014(8) C19 0.113(8) 0.106(6) 0.138(8) -0.018(6) 0.012(6) 0.008(6) C25 0.227(15) 0.174(10) 0.214(13) -0.070(10) 0.047(11) -0.025(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 Cl1 2.154(3) . ? Fe1 Cl3 2.163(3) . ? Fe1 Cl4 2.181(4) . ? Fe1 Cl2 2.198(3) . ? O1 C1 1.333(7) . ? O1 C5 1.370(8) . ? C6 C7 1.369(8) . ? C6 C11 1.393(9) . ? C6 C1 1.495(9) . ? C3 C4 1.395(9) . ? C3 C2 1.422(8) . ? C3 C12 1.460(9) . ? O2 C24 1.358(8) . ? O2 C9 1.373(7) . ? C1 C2 1.363(8) . ? C5 C4 1.342(9) . ? C5 C18 1.469(10) . ? C11 C10 1.358(8) . ? C11 H11 0.9300 . ? C7 C8 1.426(8) . ? C7 H7 0.9300 . ? C9 C10 1.364(9) . ? C9 C8 1.420(9) . ? C8 H8 0.9300 . ? C17 C16 1.419(11) . ? C17 C12 1.424(9) . ? C17 H17 0.9300 . ? C12 C13 1.363(9) . ? C2 H2 0.9300 . ? C15 C14 1.333(10) . ? C15 C16 1.349(12) . ? C15 H15 0.9300 . ? C4 H4 0.9300 . ? C18 C23 1.362(9) . ? C18 C19 1.419(9) . ? C10 H10 0.9300 . ? O3 C25 1.361(9) . ? O3 C21 1.419(10) . ? C22 C23 1.370(10) . ? C22 C21 1.385(13) . ? C22 H22 0.9300 . ? C20 C21 1.368(12) . ? C20 C19 1.377(11) . ? C20 H20 0.9300 . ? C14 C13 1.401(10) . ? C14 H14 0.9300 . ? C16 H16 0.9300 . ? C23 H23 0.9300 . ? C13 H13 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C19 H19 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Fe1 Cl3 108.18(12) . . ? Cl1 Fe1 Cl4 111.27(18) . . ? Cl3 Fe1 Cl4 110.32(17) . . ? Cl1 Fe1 Cl2 111.15(14) . . ? Cl3 Fe1 Cl2 111.04(13) . . ? Cl4 Fe1 Cl2 104.88(14) . . ? C1 O1 C5 120.5(6) . . ? C7 C6 C11 119.2(7) . . ? C7 C6 C1 119.3(7) . . ? C11 C6 C1 121.4(7) . . ? C4 C3 C2 113.9(7) . . ? C4 C3 C12 125.1(7) . . ? C2 C3 C12 121.0(7) . . ? C24 O2 C9 119.1(7) . . ? O1 C1 C2 120.9(7) . . ? O1 C1 C6 111.6(6) . . ? C2 C1 C6 127.4(7) . . ? C4 C5 O1 119.2(7) . . ? C4 C5 C18 131.2(8) . . ? O1 C5 C18 109.5(7) . . ? C10 C11 C6 119.7(7) . . ? C10 C11 H11 120.1 . . ? C6 C11 H11 120.1 . . ? C6 C7 C8 122.7(7) . . ? C6 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? C10 C9 O2 114.6(7) . . ? C10 C9 C8 121.2(7) . . ? O2 C9 C8 124.2(7) . . ? C9 C8 C7 115.1(7) . . ? C9 C8 H8 122.4 . . ? C7 C8 H8 122.4 . . ? C16 C17 C12 115.9(8) . . ? C16 C17 H17 122.1 . . ? C12 C17 H17 122.1 . . ? C13 C12 C17 118.8(8) . . ? C13 C12 C3 123.0(8) . . ? C17 C12 C3 118.2(8) . . ? C1 C2 C3 121.5(7) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C14 C15 C16 117.5(9) . . ? C14 C15 H15 121.3 . . ? C16 C15 H15 121.3 . . ? C5 C4 C3 124.1(7) . . ? C5 C4 H4 118.0 . . ? C3 C4 H4 118.0 . . ? C23 C18 C19 118.1(8) . . ? C23 C18 C5 123.0(8) . . ? C19 C18 C5 118.9(8) . . ? C11 C10 C9 122.0(7) . . ? C11 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C25 O3 C21 115.3(9) . . ? C23 C22 C21 117.0(9) . . ? C23 C22 H22 121.5 . . ? C21 C22 H22 121.5 . . ? C21 C20 C19 119.9(9) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C15 C14 C13 122.2(9) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C15 C16 C17 124.7(10) . . ? C15 C16 H16 117.7 . . ? C17 C16 H16 117.7 . . ? C18 C23 C22 123.5(8) . . ? C18 C23 H23 118.2 . . ? C22 C23 H23 118.2 . . ? C12 C13 C14 121.0(8) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C20 C21 C22 122.2(8) . . ? C20 C21 O3 125.4(12) . . ? C22 C21 O3 112.5(12) . . ? O2 C24 H24A 109.5 . . ? O2 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O2 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 C19 C18 119.3(8) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? O3 C25 H25A 109.5 . . ? O3 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O3 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.286 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.055 data_3d _database_code_depnum_ccdc_archive 'CCDC 825999' #TrackingRef 'pyrylium ferric chlorate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H23 Cl4 Fe O4' _chemical_formula_weight 597.09 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M '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 7.772(6) _cell_length_b 19.769(16) _cell_length_c 17.515(14) _cell_angle_alpha 90.00 _cell_angle_beta 92.980(10) _cell_angle_gamma 90.00 _cell_volume 2688(4) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 6088 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 27.55 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1220 _exptl_absorpt_coefficient_mu 0.989 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 'Bruker SMART CCD area-detector' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 15171 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0594 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.55 _reflns_number_total 6088 _reflns_number_gt 3636 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0596P)^2^+0.0000P] 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 0 _refine_ls_number_reflns 6088 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0981 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.51316(6) 0.26064(2) 0.39718(3) 0.04432(15) Uani 1 1 d . . . Cl2 Cl 0.74121(13) 0.24465(5) 0.33041(6) 0.0728(3) Uani 1 1 d . . . Cl4 Cl 0.45414(13) 0.17263(5) 0.46616(6) 0.0739(3) Uani 1 1 d . . . Cl1 Cl 0.28586(14) 0.27791(5) 0.31905(6) 0.0761(3) Uani 1 1 d . . . Cl3 Cl 0.56744(13) 0.34824(5) 0.47095(6) 0.0761(3) Uani 1 1 d . . . O1 O 0.2494(3) 0.06927(9) 0.04717(10) 0.0409(5) Uani 1 1 d . . . O2 O 0.6631(3) -0.02921(11) 0.34784(12) 0.0601(6) Uani 1 1 d . . . O4 O 0.0456(3) -0.09804(10) -0.24539(12) 0.0589(6) Uani 1 1 d . . . C5 C 0.1505(4) 0.09399(14) -0.01324(15) 0.0388(7) Uani 1 1 d . . . C3 C 0.1042(4) 0.19493(14) 0.06021(15) 0.0397(7) Uani 1 1 d . . . C4 C 0.0810(4) 0.15715(13) -0.00667(16) 0.0394(7) Uani 1 1 d . . . H4 H 0.0166 0.1754 -0.0479 0.047 Uiso 1 1 calc R . . C13 C 0.0154(4) 0.25893(13) 0.07069(17) 0.0389(7) Uani 1 1 d . . . C7 C 0.4156(4) -0.00083(14) 0.16583(17) 0.0433(7) Uani 1 1 d . . . H7 H 0.3728 -0.0243 0.1230 0.052 Uiso 1 1 calc R . . C6 C 0.3880(4) 0.06831(13) 0.17044(15) 0.0369(7) Uani 1 1 d . . . C20 C 0.1280(4) 0.04697(13) -0.07619(16) 0.0375(7) Uani 1 1 d . . . C2 C 0.2102(4) 0.16656(14) 0.11943(16) 0.0406(7) Uani 1 1 d . . . H2 H 0.2316 0.1910 0.1643 0.049 Uiso 1 1 calc R . . C24 C 0.1646(4) -0.06550(14) -0.12638(17) 0.0464(8) Uani 1 1 d . . . H24 H 0.2078 -0.1092 -0.1205 0.056 Uiso 1 1 calc R . . O3 O -0.2438(3) 0.43929(10) 0.10481(13) 0.0626(6) Uani 1 1 d . . . C8 C 0.5058(4) -0.03562(14) 0.22384(17) 0.0443(7) Uani 1 1 d . . . H8 H 0.5208 -0.0822 0.2204 0.053 Uiso 1 1 calc R . . C1 C 0.2819(4) 0.10439(14) 0.11267(16) 0.0397(7) Uani 1 1 d . . . C22 C 0.0101(4) 0.01816(15) -0.20372(17) 0.0465(8) Uani 1 1 d . . . H22 H -0.0491 0.0306 -0.2490 0.056 Uiso 1 1 calc R . . C21 C 0.0387(4) 0.06469(14) -0.14467(16) 0.0445(7) Uani 1 1 d . . . H21 H -0.0026 0.1086 -0.1509 0.053 Uiso 1 1 calc R . . C23 C 0.0727(4) -0.04775(15) -0.19321(17) 0.0441(7) Uani 1 1 d . . . C17 C -0.0985(4) 0.36422(15) 0.01910(17) 0.0454(7) Uani 1 1 d . . . H17 H -0.1148 0.3937 -0.0220 0.054 Uiso 1 1 calc R . . C25 C 0.1922(4) -0.01932(14) -0.06917(17) 0.0443(7) Uani 1 1 d . . . H25 H 0.2546 -0.0319 -0.0247 0.053 Uiso 1 1 calc R . . C11 C 0.4607(4) 0.10323(14) 0.23399(17) 0.0461(8) Uani 1 1 d . . . H11 H 0.4471 0.1498 0.2376 0.055 Uiso 1 1 calc R . . C14 C -0.0457(4) 0.27726(15) 0.14182(17) 0.0466(8) Uani 1 1 d . . . H14 H -0.0268 0.2485 0.1834 0.056 Uiso 1 1 calc R . . C10 C 0.5521(4) 0.06866(15) 0.29089(17) 0.0503(8) Uani 1 1 d . . . H10 H 0.6002 0.0923 0.3326 0.060 Uiso 1 1 calc R . . C18 C -0.0144(4) 0.30353(15) 0.00973(16) 0.0444(7) Uani 1 1 d . . . H18 H 0.0231 0.2921 -0.0382 0.053 Uiso 1 1 calc R . . C16 C -0.1590(4) 0.38129(14) 0.08989(17) 0.0445(7) Uani 1 1 d . . . C9 C 0.5736(4) -0.00051(15) 0.28708(17) 0.0447(7) Uani 1 1 d . . . C15 C -0.1330(4) 0.33681(15) 0.15117(17) 0.0522(8) Uani 1 1 d . . . H15 H -0.1749 0.3475 0.1985 0.063 Uiso 1 1 calc R . . C26 C -0.0402(5) -0.08262(19) -0.31728(19) 0.0708(11) Uani 1 1 d . . . H26A H -0.1492 -0.0618 -0.3089 0.106 Uiso 1 1 calc R . . H26B H -0.0586 -0.1235 -0.3461 0.106 Uiso 1 1 calc R . . H26C H 0.0294 -0.0522 -0.3452 0.106 Uiso 1 1 calc R . . C19 C -0.2805(5) 0.48506(17) 0.0438(2) 0.0712(11) Uani 1 1 d . . . H19A H -0.1745 0.5013 0.0247 0.107 Uiso 1 1 calc R . . H19B H -0.3457 0.5225 0.0618 0.107 Uiso 1 1 calc R . . H19C H -0.3460 0.4623 0.0035 0.107 Uiso 1 1 calc R . . C12 C 0.6790(5) -0.10136(18) 0.3487(2) 0.0736(11) Uani 1 1 d . . . H12A H 0.5664 -0.1214 0.3451 0.110 Uiso 1 1 calc R . . H12B H 0.7386 -0.1154 0.3954 0.110 Uiso 1 1 calc R . . H12C H 0.7427 -0.1156 0.3060 0.110 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0490(3) 0.0371(2) 0.0468(3) -0.00339(19) 0.0024(2) -0.00026(19) Cl2 0.0716(7) 0.0848(7) 0.0641(6) -0.0006(5) 0.0250(5) 0.0022(5) Cl4 0.0789(7) 0.0622(5) 0.0818(7) 0.0226(5) 0.0169(5) -0.0026(5) Cl1 0.0778(7) 0.0732(6) 0.0744(7) -0.0063(5) -0.0237(5) 0.0143(5) Cl3 0.0760(7) 0.0611(6) 0.0909(7) -0.0334(5) 0.0023(5) -0.0076(5) O1 0.0460(13) 0.0386(10) 0.0378(12) 0.0012(9) -0.0012(9) 0.0009(9) O2 0.0625(16) 0.0689(15) 0.0474(14) 0.0077(11) -0.0109(11) 0.0147(12) O4 0.0740(17) 0.0503(13) 0.0524(14) -0.0127(11) 0.0038(12) -0.0023(11) C5 0.0361(18) 0.0456(16) 0.0347(17) 0.0084(13) 0.0012(13) -0.0025(13) C3 0.0400(18) 0.0431(16) 0.0361(17) 0.0022(13) 0.0019(13) -0.0064(13) C4 0.0407(18) 0.0410(16) 0.0363(17) 0.0062(13) -0.0002(13) 0.0049(13) C13 0.0357(18) 0.0394(15) 0.0412(17) 0.0003(13) -0.0004(13) 0.0005(13) C7 0.046(2) 0.0443(17) 0.0387(17) -0.0051(14) -0.0039(14) -0.0006(14) C6 0.0363(18) 0.0379(15) 0.0365(16) -0.0013(12) 0.0016(12) 0.0029(12) C20 0.0369(18) 0.0376(15) 0.0383(17) 0.0056(12) 0.0051(13) 0.0011(12) C2 0.0396(18) 0.0461(17) 0.0355(17) 0.0016(13) -0.0035(13) -0.0009(14) C24 0.051(2) 0.0392(16) 0.049(2) 0.0053(14) 0.0053(15) 0.0036(14) O3 0.0767(18) 0.0514(13) 0.0601(15) -0.0044(11) 0.0062(12) 0.0215(12) C8 0.0421(19) 0.0391(16) 0.051(2) 0.0029(14) -0.0014(15) 0.0028(14) C1 0.0385(18) 0.0453(16) 0.0354(17) 0.0007(13) 0.0024(13) -0.0075(13) C22 0.047(2) 0.0525(18) 0.0397(18) 0.0030(14) 0.0019(14) 0.0016(15) C21 0.047(2) 0.0380(16) 0.0482(19) -0.0001(14) 0.0032(14) 0.0006(14) C23 0.0407(19) 0.0448(17) 0.0483(19) -0.0095(14) 0.0147(14) -0.0069(14) C17 0.050(2) 0.0460(17) 0.0398(18) 0.0070(14) -0.0007(14) 0.0030(15) C25 0.048(2) 0.0439(16) 0.0415(18) 0.0036(14) 0.0031(14) 0.0067(14) C11 0.052(2) 0.0364(15) 0.0496(19) -0.0071(14) -0.0038(15) 0.0061(14) C14 0.053(2) 0.0508(18) 0.0358(18) 0.0055(14) 0.0010(14) -0.0007(15) C10 0.054(2) 0.0521(19) 0.0435(19) -0.0110(15) -0.0055(15) 0.0046(16) C18 0.049(2) 0.0518(18) 0.0326(17) 0.0001(14) 0.0009(13) 0.0013(15) C16 0.0427(19) 0.0447(17) 0.0459(19) -0.0009(14) 0.0009(14) 0.0002(14) C9 0.0389(19) 0.0556(19) 0.0393(19) 0.0064(14) -0.0006(14) 0.0066(14) C15 0.061(2) 0.0533(19) 0.0436(19) -0.0056(15) 0.0110(16) 0.0077(16) C26 0.083(3) 0.083(3) 0.047(2) -0.0188(19) 0.0032(19) -0.011(2) C19 0.080(3) 0.057(2) 0.075(3) 0.0007(19) -0.007(2) 0.0222(19) C12 0.075(3) 0.073(2) 0.072(3) 0.027(2) -0.009(2) 0.023(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 Cl4 2.1807(15) . ? Fe1 Cl3 2.1886(15) . ? Fe1 Cl2 2.1965(17) . ? Fe1 Cl1 2.2043(16) . ? O1 C1 1.353(3) . ? O1 C5 1.366(3) . ? O2 C9 1.364(3) . ? O2 C12 1.432(4) . ? O4 C23 1.359(3) . ? O4 C26 1.427(4) . ? C5 C4 1.368(4) . ? C5 C20 1.446(4) . ? C3 C4 1.393(4) . ? C3 C2 1.407(4) . ? C3 C13 1.457(4) . ? C4 H4 0.9300 . ? C13 C18 1.395(4) . ? C13 C14 1.404(4) . ? C7 C6 1.386(4) . ? C7 C8 1.387(4) . ? C7 H7 0.9300 . ? C6 C11 1.403(4) . ? C6 C1 1.458(4) . ? C20 C21 1.399(4) . ? C20 C25 1.405(4) . ? C2 C1 1.357(4) . ? C2 H2 0.9300 . ? C24 C25 1.364(4) . ? C24 C23 1.385(4) . ? C24 H24 0.9300 . ? O3 C16 1.354(4) . ? O3 C19 1.418(4) . ? C8 C9 1.388(4) . ? C8 H8 0.9300 . ? C22 C21 1.393(4) . ? C22 C23 1.399(4) . ? C22 H22 0.9300 . ? C21 H21 0.9300 . ? C17 C18 1.380(4) . ? C17 C16 1.390(4) . ? C17 H17 0.9300 . ? C25 H25 0.9300 . ? C11 C10 1.375(4) . ? C11 H11 0.9300 . ? C14 C15 1.373(4) . ? C14 H14 0.9300 . ? C10 C9 1.380(4) . ? C10 H10 0.9300 . ? C18 H18 0.9300 . ? C16 C15 1.394(4) . ? C15 H15 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl4 Fe1 Cl3 110.11(7) . . ? Cl4 Fe1 Cl2 112.27(5) . . ? Cl3 Fe1 Cl2 106.98(5) . . ? Cl4 Fe1 Cl1 106.42(6) . . ? Cl3 Fe1 Cl1 111.57(5) . . ? Cl2 Fe1 Cl1 109.55(7) . . ? C1 O1 C5 123.1(2) . . ? C9 O2 C12 117.5(3) . . ? C23 O4 C26 119.1(3) . . ? O1 C5 C4 118.1(2) . . ? O1 C5 C20 113.7(2) . . ? C4 C5 C20 128.2(3) . . ? C4 C3 C2 116.8(3) . . ? C4 C3 C13 122.0(3) . . ? C2 C3 C13 121.1(3) . . ? C5 C4 C3 121.7(3) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C18 C13 C14 117.7(3) . . ? C18 C13 C3 120.9(3) . . ? C14 C13 C3 121.4(3) . . ? C6 C7 C8 121.3(3) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C7 C6 C11 118.3(3) . . ? C7 C6 C1 121.7(3) . . ? C11 C6 C1 120.0(3) . . ? C21 C20 C25 117.8(3) . . ? C21 C20 C5 121.9(2) . . ? C25 C20 C5 120.3(3) . . ? C1 C2 C3 121.6(3) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C25 C24 C23 120.4(3) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C16 O3 C19 118.4(3) . . ? C7 C8 C9 119.6(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? O1 C1 C2 118.6(3) . . ? O1 C1 C6 114.3(2) . . ? C2 C1 C6 127.0(3) . . ? C21 C22 C23 118.4(3) . . ? C21 C22 H22 120.8 . . ? C23 C22 H22 120.8 . . ? C22 C21 C20 121.6(3) . . ? C22 C21 H21 119.2 . . ? C20 C21 H21 119.2 . . ? O4 C23 C24 116.0(3) . . ? O4 C23 C22 123.5(3) . . ? C24 C23 C22 120.5(3) . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C24 C25 C20 121.2(3) . . ? C24 C25 H25 119.4 . . ? C20 C25 H25 119.4 . . ? C10 C11 C6 120.1(3) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? C15 C14 C13 121.3(3) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C11 C10 C9 121.1(3) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C17 C18 C13 121.3(3) . . ? C17 C18 H18 119.4 . . ? C13 C18 H18 119.4 . . ? O3 C16 C17 124.6(3) . . ? O3 C16 C15 116.0(3) . . ? C17 C16 C15 119.4(3) . . ? O2 C9 C10 115.6(3) . . ? O2 C9 C8 124.9(3) . . ? C10 C9 C8 119.5(3) . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? O4 C26 H26A 109.5 . . ? O4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.434 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.057 # = = = END data_1 _database_code_depnum_ccdc_archive 'CCDC 873588' #TrackingRef 'revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H25 Cl4 Fe O3' _chemical_formula_weight 619.14 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' Cl Cl 0.1484 0.1585 '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' _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 10.4870(6) _cell_length_b 32.446(2) _cell_length_c 9.5526(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.715(4) _cell_angle_gamma 90.00 _cell_volume 3096.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 275(2) _cell_measurement_reflns_used 7103 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 27.52 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1268 _exptl_absorpt_coefficient_mu 0.859 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8204 _exptl_absorpt_correction_T_max 0.8607 _exptl_absorpt_process_details 'Higashi (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 275(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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 'Bruker SMART CCD area' _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 20499 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.52 _reflns_number_total 7103 _reflns_number_gt 3984 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXP97 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' _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^)+(0.0887P)^2^+1.3126P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef constr _refine_ls_number_reflns 7103 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1069 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1943 _refine_ls_wR_factor_gt 0.1643 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.003 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 O1 O 0.2676(3) 0.20389(7) 0.2697(3) 0.0661(6) Uani 1 1 d . . . C1 C 0.3616(4) 0.17555(10) 0.3279(3) 0.0560(8) Uani 1 1 d . . . C2 C 0.3249(3) 0.13452(10) 0.3247(3) 0.0547(8) Uani 1 1 d . . . C3 C 0.1901(3) 0.12354(10) 0.2623(3) 0.0524(8) Uani 1 1 d . . . C4 C 0.0952(3) 0.15462(11) 0.2031(4) 0.0567(8) Uani 1 1 d . . . C5 C 0.1389(4) 0.19380(11) 0.2098(4) 0.0593(9) Uani 1 1 d . . . H5 H 0.0773 0.2146 0.1712 0.071 Uiso 1 1 calc R . . C6 C 0.4950(4) 0.19371(11) 0.3848(4) 0.0636(9) Uani 1 1 d . . . C7 C 0.5294(5) 0.22707(14) 0.3122(5) 0.0866(12) Uani 1 1 d . . . H7 H 0.4671 0.2382 0.2298 0.104 Uiso 1 1 calc R . . C8 C 0.6567(6) 0.24350(17) 0.3633(7) 0.1105(17) Uani 1 1 d . . . H8 H 0.6792 0.2660 0.3151 0.133 Uiso 1 1 calc R . . C9 C 0.7497(5) 0.22740(18) 0.4829(6) 0.1028(16) Uani 1 1 d . . . H9 H 0.8360 0.2381 0.5139 0.123 Uiso 1 1 calc R . . C10 C 0.7151(5) 0.19547(16) 0.5568(6) 0.0968(15) Uani 1 1 d . . . H10 H 0.7773 0.1852 0.6410 0.116 Uiso 1 1 calc R . . C11 C 0.5899(4) 0.17835(14) 0.5086(5) 0.0792(11) Uani 1 1 d . . . H11 H 0.5685 0.1563 0.5593 0.095 Uiso 1 1 calc R . . C12 C 0.4282(4) 0.10271(11) 0.3865(4) 0.0662(9) Uani 1 1 d . . . C13 C 0.4310(5) 0.08089(13) 0.5108(5) 0.0838(12) Uani 1 1 d . . . H13 H 0.3637 0.0848 0.5543 0.101 Uiso 1 1 calc R . . C14 C 0.5327(7) 0.05319(17) 0.5716(7) 0.116(2) Uani 1 1 d . . . H14 H 0.5351 0.0389 0.6567 0.140 Uiso 1 1 calc R . . C15 C 0.6283(7) 0.04707(19) 0.5067(9) 0.136(3) Uani 1 1 d . . . H15 H 0.6966 0.0283 0.5479 0.164 Uiso 1 1 calc R . . C16 C 0.6278(6) 0.0677(2) 0.3815(8) 0.125(2) Uani 1 1 d . . . H16 H 0.6945 0.0628 0.3379 0.150 Uiso 1 1 calc R . . C17 C 0.5268(4) 0.09601(15) 0.3199(5) 0.0908(13) Uani 1 1 d . . . H17 H 0.5254 0.1103 0.2351 0.109 Uiso 1 1 calc R . . C18 C 0.1456(3) 0.08014(11) 0.2572(4) 0.0590(8) Uani 1 1 d . . . C19 C 0.1908(4) 0.05085(11) 0.1772(5) 0.0732(10) Uani 1 1 d . . . H19 H 0.2519 0.0584 0.1287 0.088 Uiso 1 1 calc R . . C20 C 0.1458(5) 0.01083(14) 0.1691(6) 0.0941(14) Uani 1 1 d . . . H20 H 0.1757 -0.0085 0.1143 0.113 Uiso 1 1 calc R . . C21 C 0.0584(6) -0.00055(16) 0.2407(7) 0.1098(19) Uani 1 1 d . . . H21 H 0.0284 -0.0277 0.2346 0.132 Uiso 1 1 calc R . . C22 C 0.0134(5) 0.02762(19) 0.3225(6) 0.1084(19) Uani 1 1 d . . . H22 H -0.0451 0.0194 0.3734 0.130 Uiso 1 1 calc R . . C23 C 0.0556(4) 0.06850(14) 0.3289(4) 0.0801(11) Uani 1 1 d . . . H23 H 0.0231 0.0878 0.3814 0.096 Uiso 1 1 calc R . . C24 C -0.0491(4) 0.14756(11) 0.1253(4) 0.0640(9) Uani 1 1 d . . . C25 C -0.0873(4) 0.12260(13) 0.0021(4) 0.0738(10) Uani 1 1 d . . . H25 H -0.0227 0.1085 -0.0277 0.089 Uiso 1 1 calc R . . C26 C -0.2211(5) 0.11854(16) -0.0769(6) 0.0945(14) Uani 1 1 d . . . H26 H -0.2466 0.1018 -0.1598 0.113 Uiso 1 1 calc R . . C27 C -0.3149(5) 0.13897(18) -0.0333(8) 0.1121(19) Uani 1 1 d . . . H27 H -0.4047 0.1364 -0.0873 0.135 Uiso 1 1 calc R . . C28 C -0.2793(5) 0.16328(18) 0.0888(8) 0.115(2) Uani 1 1 d . . . H28 H -0.3451 0.1768 0.1183 0.138 Uiso 1 1 calc R . . C29 C -0.1463(4) 0.16804(14) 0.1691(6) 0.0887(13) Uani 1 1 d . . . H29 H -0.1222 0.1849 0.2518 0.106 Uiso 1 1 calc R . . Fe1 Fe 0.15868(6) 0.169073(17) 0.76978(6) 0.0688(2) Uani 1 1 d . . . Cl1 Cl 0.23033(19) 0.19578(5) 0.60002(15) 0.1288(6) Uani 1 1 d . . . Cl2 Cl 0.03470(11) 0.21434(3) 0.83733(12) 0.0783(3) Uani 1 1 d . . . Cl3 Cl 0.0398(2) 0.11431(5) 0.6818(2) 0.1527(8) Uani 1 1 d . . . Cl4 Cl 0.32338(17) 0.15282(7) 0.96150(16) 0.1562(8) Uani 1 1 d . . . O2 O 0.3597(10) 0.0209(2) 0.8890(9) 0.314(5) Uani 1 1 d . . . H2A H 0.3032 0.0261 0.8200 0.377 Uiso 1 1 d R . . H2B H 0.3900 0.0068 0.9653 0.377 Uiso 1 1 d R . . O3 O 0.5545(13) 0.0324(2) 0.9985(10) 0.374(8) Uani 1 1 d . . . H3A H 0.6350 0.0253 1.0511 0.449 Uiso 1 1 d R . . H3B H 0.5309 0.0523 0.9486 0.449 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 O1 0.0800(17) 0.0552(14) 0.0592(14) -0.0008(11) 0.0153(13) -0.0004(13) C1 0.066(2) 0.056(2) 0.0463(17) -0.0013(14) 0.0172(15) 0.0006(17) C2 0.062(2) 0.056(2) 0.0445(16) -0.0013(14) 0.0130(15) 0.0032(16) C3 0.062(2) 0.0561(19) 0.0393(15) -0.0027(13) 0.0159(14) 0.0024(15) C4 0.064(2) 0.059(2) 0.0504(18) -0.0019(15) 0.0220(16) 0.0045(17) C5 0.063(2) 0.055(2) 0.0551(19) -0.0037(15) 0.0106(16) 0.0115(17) C6 0.072(2) 0.060(2) 0.058(2) -0.0091(16) 0.0183(18) -0.0066(18) C7 0.098(3) 0.078(3) 0.079(3) 0.002(2) 0.020(2) -0.018(2) C8 0.120(4) 0.101(4) 0.111(4) 0.000(3) 0.036(3) -0.049(3) C9 0.086(3) 0.112(4) 0.102(4) -0.021(3) 0.017(3) -0.035(3) C10 0.086(3) 0.095(4) 0.090(3) -0.012(3) -0.002(3) -0.014(3) C11 0.077(3) 0.080(3) 0.069(2) -0.004(2) 0.006(2) -0.014(2) C12 0.066(2) 0.058(2) 0.063(2) -0.0054(17) 0.0021(18) 0.0006(17) C13 0.091(3) 0.071(3) 0.072(3) 0.014(2) 0.000(2) -0.004(2) C14 0.125(5) 0.083(4) 0.110(4) 0.022(3) -0.012(4) 0.003(3) C15 0.130(5) 0.098(4) 0.133(6) -0.004(4) -0.032(5) 0.043(4) C16 0.096(4) 0.132(5) 0.130(5) -0.016(4) 0.008(4) 0.045(4) C17 0.083(3) 0.093(3) 0.086(3) -0.008(2) 0.011(2) 0.024(2) C18 0.063(2) 0.058(2) 0.0507(18) 0.0087(15) 0.0091(16) 0.0012(16) C19 0.077(3) 0.057(2) 0.082(3) -0.0056(19) 0.017(2) -0.0020(19) C20 0.091(3) 0.060(3) 0.113(4) -0.006(2) 0.005(3) 0.000(2) C21 0.097(4) 0.062(3) 0.140(5) 0.028(3) -0.009(4) -0.006(3) C22 0.087(3) 0.110(4) 0.115(4) 0.054(4) 0.012(3) -0.024(3) C23 0.083(3) 0.086(3) 0.071(3) 0.018(2) 0.023(2) 0.000(2) C24 0.062(2) 0.061(2) 0.069(2) 0.0106(17) 0.0206(18) 0.0038(17) C25 0.069(2) 0.076(3) 0.072(2) -0.001(2) 0.015(2) -0.004(2) C26 0.075(3) 0.095(3) 0.098(3) 0.004(3) 0.004(3) -0.012(3) C27 0.063(3) 0.089(4) 0.166(6) 0.024(4) 0.008(3) -0.009(3) C28 0.069(3) 0.101(4) 0.188(7) 0.000(4) 0.056(4) 0.011(3) C29 0.076(3) 0.082(3) 0.115(4) -0.009(2) 0.040(3) 0.005(2) Fe1 0.0858(4) 0.0696(4) 0.0530(3) 0.0033(2) 0.0241(3) 0.0049(3) Cl1 0.2061(16) 0.1233(11) 0.0857(8) -0.0056(7) 0.0872(10) -0.0270(11) Cl2 0.0859(7) 0.0681(6) 0.0796(7) -0.0037(5) 0.0235(5) 0.0042(5) Cl3 0.233(2) 0.0887(10) 0.1647(16) -0.0502(10) 0.1028(15) -0.0515(11) Cl4 0.1257(12) 0.261(2) 0.0775(8) 0.0285(11) 0.0248(8) 0.0988(14) O2 0.534(14) 0.217(7) 0.324(10) -0.142(7) 0.330(10) -0.150(8) O3 0.76(2) 0.190(7) 0.353(10) -0.174(7) 0.444(13) -0.276(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.336(4) . ? O1 C1 1.339(4) . ? C1 C2 1.383(5) . ? C1 C6 1.462(5) . ? C2 C3 1.403(4) . ? C2 C12 1.483(5) . ? C3 C4 1.409(5) . ? C3 C18 1.480(5) . ? C4 C5 1.346(5) . ? C4 C24 1.487(5) . ? C5 H5 0.9300 . ? C6 C11 1.386(5) . ? C6 C7 1.391(5) . ? C7 C8 1.381(6) . ? C7 H7 0.9300 . ? C8 C9 1.360(7) . ? C8 H8 0.9300 . ? C9 C10 1.364(7) . ? C9 H9 0.9300 . ? C10 C11 1.370(6) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.376(6) . ? C12 C17 1.385(6) . ? C13 C14 1.381(7) . ? C13 H13 0.9300 . ? C14 C15 1.344(9) . ? C14 H14 0.9300 . ? C15 C16 1.369(10) . ? C15 H15 0.9300 . ? C16 C17 1.390(7) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C23 1.377(5) . ? C18 C19 1.390(5) . ? C19 C20 1.376(6) . ? C19 H19 0.9300 . ? C20 C21 1.351(8) . ? C20 H20 0.9300 . ? C21 C22 1.376(8) . ? C21 H21 0.9300 . ? C22 C23 1.394(7) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.384(5) . ? C24 C29 1.384(5) . ? C25 C26 1.383(6) . ? C25 H25 0.9300 . ? C26 C27 1.353(8) . ? C26 H26 0.9300 . ? C27 C28 1.363(9) . ? C27 H27 0.9300 . ? C28 C29 1.381(7) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? Fe1 Cl4 2.1658(14) . ? Fe1 Cl1 2.1649(13) . ? Fe1 Cl2 2.1852(12) . ? Fe1 Cl3 2.1860(16) . ? O2 H2A 0.7600 . ? O2 H2B 0.8363 . ? O3 H3A 0.8714 . ? O3 H3B 0.7971 . ? 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 O1 C1 122.0(3) . . ? O1 C1 C2 119.2(3) . . ? O1 C1 C6 112.2(3) . . ? C2 C1 C6 128.6(3) . . ? C1 C2 C3 119.4(3) . . ? C1 C2 C12 119.8(3) . . ? C3 C2 C12 120.8(3) . . ? C2 C3 C4 119.1(3) . . ? C2 C3 C18 121.5(3) . . ? C4 C3 C18 119.4(3) . . ? C5 C4 C3 117.9(3) . . ? C5 C4 C24 116.7(3) . . ? C3 C4 C24 125.3(3) . . ? O1 C5 C4 122.5(3) . . ? O1 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? C11 C6 C7 118.5(4) . . ? C11 C6 C1 122.0(3) . . ? C7 C6 C1 119.5(3) . . ? C8 C7 C6 119.6(4) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C9 C8 C7 121.1(5) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C10 C9 C8 119.4(5) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 120.8(5) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C6 120.5(4) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C13 C12 C17 119.6(4) . . ? C13 C12 C2 121.5(4) . . ? C17 C12 C2 118.9(4) . . ? C12 C13 C14 120.5(5) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 119.5(6) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 121.7(6) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C15 C16 C17 119.5(6) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C12 C17 C16 119.2(5) . . ? C12 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C23 C18 C19 119.1(4) . . ? C23 C18 C3 120.1(3) . . ? C19 C18 C3 120.8(3) . . ? C20 C19 C18 120.5(4) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C21 C20 C19 120.2(5) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 120.6(5) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C21 C22 C23 119.9(5) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C18 C23 C22 119.7(5) . . ? C18 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C25 C24 C29 119.3(4) . . ? C25 C24 C4 120.1(3) . . ? C29 C24 C4 120.4(4) . . ? C24 C25 C26 120.2(4) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C27 C26 C25 119.9(5) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C26 C27 C28 120.8(5) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C27 C28 C29 120.5(5) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C28 C29 C24 119.4(5) . . ? C28 C29 H29 120.3 . . ? C24 C29 H29 120.3 . . ? Cl4 Fe1 Cl1 111.20(8) . . ? Cl4 Fe1 Cl2 107.88(6) . . ? Cl1 Fe1 Cl2 108.99(6) . . ? Cl4 Fe1 Cl3 109.99(9) . . ? Cl1 Fe1 Cl3 108.94(7) . . ? Cl2 Fe1 Cl3 109.82(6) . . ? H2A O2 H2B 150.2 . . ? H3A O3 H3B 129.0 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.459 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.052