# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_Cambridge 1500 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Maya Singh' _publ_contact_author_email mssinghbhu@yahoo.co.in _publ_section_title ; InCl3 catalyzed one-pot route to a combinatorial library of 2H-chromene-2-ones via [4 + 2] annulation of 2-hydroxyarylaldehydes with alpha-oxoketene dithioacetal under solvent-free conditions ; _publ_author_name 'Maya Singh' # Attachment '- 12f CCDC 805566 CIF.cif' data_dtsal49 _database_code_depnum_ccdc_archive 'CCDC 805566' #TrackingRef '- 12f CCDC 805566 CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C13.33 H7.33 Cl0.67 O2 S0' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 293(2) _chemical_formula_weight 223.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3853(5) _cell_length_b 9.6126(7) _cell_length_c 10.8880(7) _cell_angle_alpha 84.694(6) _cell_angle_beta 87.875(5) _cell_angle_gamma 84.710(6) _cell_volume 766.05(9) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.84562 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5538 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 28.96 _reflns_number_total 3433 _reflns_number_gt 2041 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.2614P] 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 RIDING _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3433 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1453 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _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 Cl1 Cl 0.46285(11) 0.48945(8) 0.20769(9) 0.0772(3) Uani 1 1 d . . . O1 O 0.7361(2) 0.08173(17) 0.26569(18) 0.0570(5) Uani 1 1 d . . . C13 C 0.7886(3) 0.1224(2) 0.0466(2) 0.0422(6) Uani 1 1 d . . . C12 C 0.7871(3) 0.0710(2) -0.0729(3) 0.0461(6) Uani 1 1 d . . . C14 C 0.8396(3) 0.2580(2) 0.0683(2) 0.0420(6) Uani 1 1 d . . . H14 H 0.8774 0.3172 0.0017 0.050 Uiso 1 1 calc R . . O2 O 0.7838(3) 0.2344(2) 0.39748(17) 0.0635(5) Uani 1 1 d . . . C4 C 0.7390(3) 0.0383(2) 0.1499(3) 0.0483(6) Uani 1 1 d . . . C2 C 0.8347(3) 0.3024(2) 0.1822(2) 0.0419(6) Uani 1 1 d . . . C7 C 0.7373(3) -0.0673(3) -0.0803(3) 0.0555(7) Uani 1 1 d . . . C11 C 0.8323(4) 0.1501(3) -0.1825(3) 0.0545(7) Uani 1 1 d . . . H11 H 0.8666 0.2403 -0.1791 0.065 Uiso 1 1 calc R . . C5 C 0.6920(4) -0.0990(3) 0.1412(3) 0.0648(8) Uani 1 1 d . . . H5 H 0.6612 -0.1550 0.2118 0.078 Uiso 1 1 calc R . . O3 O 1.0213(3) 0.4863(2) 0.14273(18) 0.0642(6) Uani 1 1 d . . . C3 C 0.7835(4) 0.2119(3) 0.2895(3) 0.0506(7) Uani 1 1 d . . . C8 C 0.7329(4) -0.1174(3) -0.1980(4) 0.0726(10) Uani 1 1 d . . . H8 H 0.6999 -0.2075 -0.2041 0.087 Uiso 1 1 calc R . . C1 C 0.8913(4) 0.4439(2) 0.2011(2) 0.0446(6) Uani 1 1 d . . . C15 C 0.7934(3) 0.5309(2) 0.2936(2) 0.0441(6) Uani 1 1 d . . . C20 C 0.8982(4) 0.5947(3) 0.3717(2) 0.0543(7) Uani 1 1 d . . . H20 H 1.0243 0.5826 0.3632 0.065 Uiso 1 1 calc R . . C16 C 0.6060(4) 0.5553(2) 0.3068(3) 0.0498(7) Uani 1 1 d . . . C6 C 0.6919(4) -0.1483(3) 0.0298(4) 0.0693(9) Uani 1 1 d . . . H6 H 0.6609 -0.2392 0.0248 0.083 Uiso 1 1 calc R . . C17 C 0.5265(4) 0.6373(3) 0.3948(3) 0.0597(7) Uani 1 1 d . . . H17 H 0.4005 0.6530 0.4017 0.072 Uiso 1 1 calc R . . C19 C 0.8205(5) 0.6754(3) 0.4612(3) 0.0678(8) Uani 1 1 d . . . H19 H 0.8931 0.7156 0.5137 0.081 Uiso 1 1 calc R . . C9 C 0.7756(5) -0.0377(4) -0.3020(4) 0.0763(10) Uani 1 1 d . . . H9 H 0.7707 -0.0726 -0.3786 0.092 Uiso 1 1 calc R . . C10 C 0.8269(4) 0.0972(3) -0.2940(3) 0.0682(8) Uani 1 1 d . . . H10 H 0.8578 0.1516 -0.3655 0.082 Uiso 1 1 calc R . . C18 C 0.6347(5) 0.6956(3) 0.4720(3) 0.0680(9) Uani 1 1 d . . . H18 H 0.5813 0.7496 0.5325 0.082 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 Cl1 0.0555(5) 0.0663(5) 0.1153(7) -0.0253(4) -0.0272(4) -0.0069(4) O1 0.0586(12) 0.0453(10) 0.0656(13) 0.0100(9) 0.0010(9) -0.0137(9) C13 0.0308(13) 0.0320(11) 0.0639(17) -0.0033(11) -0.0053(11) -0.0027(10) C12 0.0320(13) 0.0323(12) 0.0743(19) -0.0077(12) -0.0078(12) 0.0003(10) C14 0.0390(13) 0.0323(11) 0.0544(16) 0.0007(11) -0.0007(11) -0.0073(10) O2 0.0785(14) 0.0731(13) 0.0396(11) -0.0037(9) 0.0027(9) -0.0136(11) C4 0.0358(14) 0.0339(12) 0.0738(19) 0.0048(13) -0.0037(12) -0.0053(11) C2 0.0393(14) 0.0376(12) 0.0490(15) 0.0013(11) -0.0034(11) -0.0086(10) C7 0.0396(15) 0.0345(13) 0.095(2) -0.0173(14) -0.0150(14) 0.0009(11) C11 0.0535(17) 0.0425(14) 0.0701(19) -0.0161(14) -0.0073(14) -0.0045(12) C5 0.0562(18) 0.0383(14) 0.099(3) 0.0081(15) -0.0056(17) -0.0118(13) O3 0.0708(14) 0.0661(12) 0.0610(12) -0.0119(10) 0.0129(10) -0.0344(10) C3 0.0465(16) 0.0419(14) 0.0615(18) 0.0089(13) -0.0004(13) -0.0078(12) C8 0.058(2) 0.0428(15) 0.122(3) -0.0342(19) -0.0206(19) 0.0002(14) C1 0.0475(15) 0.0441(13) 0.0436(15) 0.0004(11) -0.0062(11) -0.0137(12) C15 0.0511(16) 0.0359(12) 0.0457(15) 0.0026(11) -0.0055(11) -0.0100(11) C20 0.0516(16) 0.0565(15) 0.0576(17) -0.0096(13) -0.0089(13) -0.0124(13) C16 0.0496(16) 0.0339(12) 0.0668(18) 0.0006(12) -0.0085(13) -0.0107(11) C6 0.0530(18) 0.0319(13) 0.124(3) -0.0035(17) -0.0119(18) -0.0116(13) C17 0.0525(17) 0.0447(14) 0.082(2) -0.0058(15) 0.0066(15) -0.0079(13) C19 0.078(2) 0.0673(19) 0.063(2) -0.0199(16) -0.0047(16) -0.0190(17) C9 0.074(2) 0.069(2) 0.093(3) -0.042(2) -0.0128(19) -0.0009(18) C10 0.073(2) 0.0613(18) 0.072(2) -0.0225(16) -0.0073(16) 0.0002(16) C18 0.083(2) 0.0541(17) 0.068(2) -0.0157(15) 0.0133(17) -0.0111(16) _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 Cl1 C16 1.737(3) . ? O1 C4 1.363(3) . ? O1 C3 1.380(3) . ? C13 C4 1.382(3) . ? C13 C12 1.435(3) . ? C13 C14 1.432(3) . ? C12 C11 1.402(4) . ? C12 C7 1.422(3) . ? C14 C2 1.347(3) . ? C14 H14 0.9300 . ? O2 C3 1.215(3) . ? C4 C5 1.409(3) . ? C2 C3 1.451(3) . ? C2 C1 1.493(3) . ? C7 C8 1.413(4) . ? C7 C6 1.414(4) . ? C11 C10 1.362(4) . ? C11 H11 0.9300 . ? C5 C6 1.342(4) . ? C5 H5 0.9300 . ? O3 C1 1.212(3) . ? C8 C9 1.352(5) . ? C8 H8 0.9300 . ? C1 C15 1.493(3) . ? C15 C16 1.386(3) . ? C15 C20 1.390(3) . ? C20 C19 1.378(4) . ? C20 H20 0.9300 . ? C16 C17 1.377(4) . ? C6 H6 0.9300 . ? C17 C18 1.371(4) . ? C17 H17 0.9300 . ? C19 C18 1.370(4) . ? C19 H19 0.9300 . ? C9 C10 1.395(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C18 H18 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 C4 O1 C3 123.0(2) . . ? C4 C13 C12 119.6(2) . . ? C4 C13 C14 116.0(2) . . ? C12 C13 C14 124.4(2) . . ? C11 C12 C7 118.4(2) . . ? C11 C12 C13 123.3(2) . . ? C7 C12 C13 118.3(2) . . ? C2 C14 C13 122.0(2) . . ? C2 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? O1 C4 C13 122.4(2) . . ? O1 C4 C5 116.2(2) . . ? C13 C4 C5 121.4(3) . . ? C14 C2 C3 121.0(2) . . ? C14 C2 C1 120.3(2) . . ? C3 C2 C1 118.6(2) . . ? C8 C7 C6 122.7(3) . . ? C8 C7 C12 118.3(3) . . ? C6 C7 C12 118.9(3) . . ? C10 C11 C12 121.2(3) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? O2 C3 O1 116.2(2) . . ? O2 C3 C2 128.2(2) . . ? O1 C3 C2 115.6(2) . . ? C9 C8 C7 121.7(3) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? O3 C1 C15 120.0(2) . . ? O3 C1 C2 119.4(2) . . ? C15 C1 C2 120.7(2) . . ? C16 C15 C20 117.2(2) . . ? C16 C15 C1 125.3(2) . . ? C20 C15 C1 117.5(2) . . ? C19 C20 C15 121.8(3) . . ? C19 C20 H20 119.1 . . ? C15 C20 H20 119.1 . . ? C17 C16 C15 121.6(2) . . ? C17 C16 Cl1 117.5(2) . . ? C15 C16 Cl1 120.9(2) . . ? C5 C6 C7 122.5(3) . . ? C5 C6 H6 118.8 . . ? C7 C6 H6 118.8 . . ? C18 C17 C16 119.4(3) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C18 C19 C20 119.1(3) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? C8 C9 C10 119.7(3) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 120.7(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C19 C18 C17 120.8(3) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 C13 C12 C11 178.9(2) . . . . ? C14 C13 C12 C11 -1.5(4) . . . . ? C4 C13 C12 C7 -1.1(3) . . . . ? C14 C13 C12 C7 178.5(2) . . . . ? C4 C13 C14 C2 -1.8(3) . . . . ? C12 C13 C14 C2 178.5(2) . . . . ? C3 O1 C4 C13 -0.6(4) . . . . ? C3 O1 C4 C5 178.2(2) . . . . ? C12 C13 C4 O1 -179.4(2) . . . . ? C14 C13 C4 O1 0.9(3) . . . . ? C12 C13 C4 C5 1.9(4) . . . . ? C14 C13 C4 C5 -177.8(2) . . . . ? C13 C14 C2 C3 2.4(4) . . . . ? C13 C14 C2 C1 179.2(2) . . . . ? C11 C12 C7 C8 -1.0(4) . . . . ? C13 C12 C7 C8 179.0(2) . . . . ? C11 C12 C7 C6 179.8(2) . . . . ? C13 C12 C7 C6 -0.2(3) . . . . ? C7 C12 C11 C10 0.8(4) . . . . ? C13 C12 C11 C10 -179.2(2) . . . . ? O1 C4 C5 C6 179.9(2) . . . . ? C13 C4 C5 C6 -1.3(4) . . . . ? C4 O1 C3 O2 -176.3(2) . . . . ? C4 O1 C3 C2 1.0(3) . . . . ? C14 C2 C3 O2 175.1(3) . . . . ? C1 C2 C3 O2 -1.8(4) . . . . ? C14 C2 C3 O1 -1.9(3) . . . . ? C1 C2 C3 O1 -178.8(2) . . . . ? C6 C7 C8 C9 179.5(3) . . . . ? C12 C7 C8 C9 0.4(4) . . . . ? C14 C2 C1 O3 -39.4(4) . . . . ? C3 C2 C1 O3 137.5(3) . . . . ? C14 C2 C1 C15 142.6(2) . . . . ? C3 C2 C1 C15 -40.5(3) . . . . ? O3 C1 C15 C16 135.0(3) . . . . ? C2 C1 C15 C16 -46.9(3) . . . . ? O3 C1 C15 C20 -43.9(3) . . . . ? C2 C1 C15 C20 134.1(2) . . . . ? C16 C15 C20 C19 1.9(4) . . . . ? C1 C15 C20 C19 -179.0(2) . . . . ? C20 C15 C16 C17 -1.0(4) . . . . ? C1 C15 C16 C17 -180.0(2) . . . . ? C20 C15 C16 Cl1 176.04(18) . . . . ? C1 C15 C16 Cl1 -2.9(3) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? C8 C7 C6 C5 -178.3(3) . . . . ? C12 C7 C6 C5 0.8(4) . . . . ? C15 C16 C17 C18 -0.5(4) . . . . ? Cl1 C16 C17 C18 -177.7(2) . . . . ? C15 C20 C19 C18 -1.3(4) . . . . ? C7 C8 C9 C10 0.6(5) . . . . ? C12 C11 C10 C9 0.1(4) . . . . ? C8 C9 C10 C11 -0.8(5) . . . . ? C20 C19 C18 C17 -0.3(5) . . . . ? C16 C17 C18 C19 1.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.236 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.044 # Attachment '- 10ja CCDC 805567 CIF.cif' data_dtsal-16r _database_code_depnum_ccdc_archive 'CCDC 805567' #TrackingRef '- 10ja CCDC 805567 CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 Fe O3' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 293(2) _chemical_formula_weight 358.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_int_tables_number 61 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 12.377(5) _cell_length_b 10.686(5) _cell_length_c 23.309(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 3083(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.993 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.84446 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8817 _diffrn_reflns_av_R_equivalents 0.1407 _diffrn_reflns_av_sigmaI/netI 0.2584 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 29.12 _reflns_number_total 3548 _reflns_number_gt 1250 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3548 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2486 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.0820 _refine_ls_goodness_of_fit_ref 0.915 _refine_ls_restrained_S_all 0.915 _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 0.89653(7) 0.28237(9) 0.94986(3) 0.0388(3) Uani 1 1 d . . . O1 O 0.7315(4) 0.4736(4) 0.84835(17) 0.0539(15) Uani 1 1 d . . . O3 O 0.5772(3) 0.1473(4) 0.78574(18) 0.0447(13) Uani 1 1 d . . . O2 O 0.5734(3) 0.2635(5) 0.86330(17) 0.0544(15) Uani 1 1 d . . . C2 C 0.7348(5) 0.2717(6) 0.8074(2) 0.0330(16) Uani 1 1 d . . . C4 C 0.6308(6) 0.0926(6) 0.7400(3) 0.0354(18) Uani 1 1 d . . . C10 C 0.7866(5) 0.2190(6) 0.7631(2) 0.0342(17) Uani 1 1 d . . . H10 H 0.8572 0.2435 0.7552 0.041 Uiso 1 1 calc R . . C1 C 0.7822(6) 0.3768(6) 0.8428(2) 0.0348(18) Uani 1 1 d . . . C9 C 0.7375(5) 0.1275(6) 0.7278(2) 0.0350(18) Uani 1 1 d . . . C20 C 0.7916(7) 0.3222(7) 1.0148(3) 0.058(2) Uani 1 1 d . . . H20 H 0.7652 0.4013 1.0237 0.070 Uiso 1 1 calc R . . C5 C 0.5769(6) 0.0051(7) 0.7086(3) 0.049(2) Uani 1 1 d . . . H5 H 0.5058 -0.0152 0.7176 0.058 Uiso 1 1 calc R . . C3 C 0.6248(6) 0.2324(7) 0.8223(3) 0.0408(19) Uani 1 1 d . . . C6 C 0.6275(6) -0.0524(7) 0.6642(3) 0.057(2) Uani 1 1 d . . . H6 H 0.5910 -0.1129 0.6430 0.068 Uiso 1 1 calc R . . C8 C 0.7862(6) 0.0674(7) 0.6814(3) 0.049(2) Uani 1 1 d . . . H8 H 0.8566 0.0885 0.6714 0.059 Uiso 1 1 calc R . . C7 C 0.7329(7) -0.0221(7) 0.6499(3) 0.059(2) Uani 1 1 d . . . H7 H 0.7672 -0.0618 0.6195 0.071 Uiso 1 1 calc R . . C15 C 0.9377(6) 0.4420(7) 0.9082(3) 0.046(2) Uani 1 1 d . . . H15 H 0.9131 0.5221 0.9166 0.056 Uiso 1 1 calc R . . C19 C 0.8846(6) 0.2674(8) 1.0373(2) 0.055(2) Uani 1 1 d . . . H19 H 0.9303 0.3025 1.0646 0.066 Uiso 1 1 calc R . . C14 C 1.0300(6) 0.3861(8) 0.9311(3) 0.056(2) Uani 1 1 d . . . H14 H 1.0769 0.4221 0.9575 0.067 Uiso 1 1 calc R . . C16 C 0.7446(6) 0.2373(10) 0.9761(3) 0.073(3) Uani 1 1 d . . . H16 H 0.6814 0.2498 0.9553 0.088 Uiso 1 1 calc R . . C11 C 0.8874(5) 0.3559(6) 0.8696(2) 0.0351(17) Uani 1 1 d . . . C13 C 1.0397(6) 0.2650(9) 0.9072(3) 0.062(2) Uani 1 1 d . . . H13 H 1.0950 0.2083 0.9145 0.074 Uiso 1 1 calc R . . C12 C 0.9512(5) 0.2454(7) 0.8704(3) 0.050(2) Uani 1 1 d . . . H12 H 0.9369 0.1724 0.8500 0.061 Uiso 1 1 calc R . . C17 C 0.8102(9) 0.1300(9) 0.9744(3) 0.081(3) Uani 1 1 d . . . H17 H 0.7981 0.0586 0.9525 0.098 Uiso 1 1 calc R . . C18 C 0.8968(7) 0.1502(8) 1.0117(3) 0.070(3) Uani 1 1 d . . . H18 H 0.9534 0.0948 1.0182 0.084 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 0.0403(6) 0.0373(6) 0.0386(5) 0.0010(5) -0.0024(5) -0.0048(6) O1 0.066(4) 0.038(3) 0.058(3) -0.002(3) -0.004(3) 0.019(3) O3 0.034(3) 0.053(4) 0.047(3) 0.001(3) 0.006(2) 0.005(3) O2 0.044(3) 0.072(4) 0.048(3) -0.005(3) 0.017(2) 0.014(3) C2 0.031(4) 0.037(5) 0.031(3) 0.008(4) 0.000(3) -0.004(4) C4 0.038(5) 0.032(5) 0.036(4) -0.003(4) -0.008(4) 0.003(4) C10 0.031(4) 0.042(5) 0.029(3) 0.001(4) 0.008(3) -0.003(4) C1 0.037(5) 0.035(5) 0.033(4) 0.008(4) 0.010(3) 0.003(4) C9 0.034(5) 0.044(5) 0.027(3) -0.002(3) 0.003(3) -0.009(4) C20 0.067(6) 0.066(7) 0.041(4) 0.012(5) 0.011(4) -0.002(5) C5 0.050(5) 0.049(6) 0.047(4) 0.002(4) -0.008(4) -0.008(4) C3 0.050(5) 0.041(5) 0.031(3) 0.004(4) 0.000(4) 0.009(4) C6 0.071(7) 0.055(6) 0.043(4) -0.008(4) -0.012(4) -0.018(5) C8 0.039(5) 0.066(6) 0.042(4) -0.002(4) 0.009(4) 0.003(4) C7 0.073(7) 0.060(6) 0.043(4) -0.008(4) 0.005(5) -0.006(5) C15 0.060(6) 0.035(5) 0.044(4) 0.003(4) 0.006(4) -0.009(4) C19 0.065(6) 0.066(6) 0.034(4) 0.010(4) -0.012(4) -0.009(5) C14 0.054(6) 0.069(7) 0.045(4) -0.014(5) -0.002(4) -0.024(5) C16 0.056(6) 0.117(10) 0.048(5) 0.025(6) -0.009(4) -0.037(6) C11 0.031(4) 0.037(5) 0.037(4) -0.003(4) 0.006(3) -0.009(4) C13 0.037(5) 0.083(8) 0.066(5) -0.014(5) -0.001(4) 0.003(5) C12 0.043(5) 0.059(6) 0.049(4) -0.014(4) -0.008(4) 0.012(4) C17 0.125(10) 0.070(8) 0.049(5) -0.003(6) 0.005(6) -0.057(7) C18 0.106(8) 0.046(6) 0.059(5) 0.016(5) 0.009(5) 0.023(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C18 2.017(7) . ? Fe1 C12 2.012(6) . ? Fe1 C17 2.030(8) . ? Fe1 C15 2.028(7) . ? Fe1 C16 2.035(8) . ? Fe1 C20 2.039(6) . ? Fe1 C14 2.037(7) . ? Fe1 C11 2.033(6) . ? Fe1 C13 2.041(7) . ? Fe1 C19 2.051(6) . ? O1 C1 1.217(7) . ? O3 C3 1.379(7) . ? O3 C4 1.386(7) . ? O2 C3 1.195(6) . ? C2 C10 1.340(7) . ? C2 C3 1.467(8) . ? C2 C1 1.513(8) . ? C4 C5 1.361(8) . ? C4 C9 1.402(8) . ? C10 C9 1.415(8) . ? C10 H10 0.9300 . ? C1 C11 1.460(8) . ? C9 C8 1.394(8) . ? C20 C19 1.395(9) . ? C20 C16 1.405(9) . ? C20 H20 0.9300 . ? C5 C6 1.359(8) . ? C5 H5 0.9300 . ? C6 C7 1.384(8) . ? C6 H6 0.9300 . ? C8 C7 1.373(8) . ? C8 H8 0.9300 . ? C7 H7 0.9300 . ? C15 C14 1.395(8) . ? C15 C11 1.429(8) . ? C15 H15 0.9300 . ? C19 C18 1.396(9) . ? C19 H19 0.9300 . ? C14 C13 1.414(9) . ? C14 H14 0.9300 . ? C16 C17 1.405(10) . ? C16 H16 0.9300 . ? C11 C12 1.421(8) . ? C13 C12 1.407(8) . ? C13 H13 0.9300 . ? C12 H12 0.9300 . ? C17 C18 1.397(10) . ? C17 H17 0.9300 . ? C18 H18 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 C18 Fe1 C12 121.3(3) . . ? C18 Fe1 C17 40.4(3) . . ? C12 Fe1 C17 106.2(3) . . ? C18 Fe1 C15 158.5(4) . . ? C12 Fe1 C15 68.8(3) . . ? C17 Fe1 C15 160.4(4) . . ? C18 Fe1 C16 67.8(3) . . ? C12 Fe1 C16 122.8(3) . . ? C17 Fe1 C16 40.4(3) . . ? C15 Fe1 C16 125.1(3) . . ? C18 Fe1 C20 67.5(3) . . ? C12 Fe1 C20 159.8(3) . . ? C17 Fe1 C20 67.8(3) . . ? C15 Fe1 C20 109.9(3) . . ? C16 Fe1 C20 40.3(3) . . ? C18 Fe1 C14 122.2(4) . . ? C12 Fe1 C14 68.7(3) . . ? C17 Fe1 C14 157.5(4) . . ? C15 Fe1 C14 40.2(2) . . ? C16 Fe1 C14 160.5(4) . . ? C20 Fe1 C14 124.2(3) . . ? C18 Fe1 C11 158.2(3) . . ? C12 Fe1 C11 41.1(2) . . ? C17 Fe1 C11 122.7(3) . . ? C15 Fe1 C11 41.2(2) . . ? C16 Fe1 C11 108.5(3) . . ? C20 Fe1 C11 124.5(3) . . ? C14 Fe1 C11 68.7(3) . . ? C18 Fe1 C13 106.4(3) . . ? C12 Fe1 C13 40.6(2) . . ? C17 Fe1 C13 121.5(4) . . ? C15 Fe1 C13 67.9(3) . . ? C16 Fe1 C13 158.0(4) . . ? C20 Fe1 C13 159.1(3) . . ? C14 Fe1 C13 40.6(3) . . ? C11 Fe1 C13 68.6(3) . . ? C18 Fe1 C19 40.1(3) . . ? C12 Fe1 C19 157.6(3) . . ? C17 Fe1 C19 67.6(3) . . ? C15 Fe1 C19 124.1(3) . . ? C16 Fe1 C19 67.4(3) . . ? C20 Fe1 C19 39.9(2) . . ? C14 Fe1 C19 108.3(3) . . ? C11 Fe1 C19 160.3(3) . . ? C13 Fe1 C19 122.7(3) . . ? C3 O3 C4 123.4(5) . . ? C10 C2 C3 120.4(6) . . ? C10 C2 C1 123.2(6) . . ? C3 C2 C1 116.3(5) . . ? C5 C4 O3 117.9(7) . . ? C5 C4 C9 122.4(6) . . ? O3 C4 C9 119.7(6) . . ? C2 C10 C9 122.3(6) . . ? C2 C10 H10 118.9 . . ? C9 C10 H10 118.9 . . ? O1 C1 C11 123.0(7) . . ? O1 C1 C2 119.2(6) . . ? C11 C1 C2 117.7(6) . . ? C4 C9 C8 116.2(6) . . ? C4 C9 C10 118.0(6) . . ? C8 C9 C10 125.7(6) . . ? C19 C20 C16 108.2(7) . . ? C19 C20 Fe1 70.5(4) . . ? C16 C20 Fe1 69.7(4) . . ? C19 C20 H20 125.9 . . ? C16 C20 H20 125.9 . . ? Fe1 C20 H20 125.5 . . ? C4 C5 C6 119.6(7) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? O2 C3 O3 116.8(6) . . ? O2 C3 C2 127.1(7) . . ? O3 C3 C2 116.1(5) . . ? C5 C6 C7 120.8(7) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C7 C8 C9 121.8(7) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C8 C7 C6 119.2(7) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C14 C15 C11 108.8(6) . . ? C14 C15 Fe1 70.3(4) . . ? C11 C15 Fe1 69.6(4) . . ? C14 C15 H15 125.6 . . ? C11 C15 H15 125.6 . . ? Fe1 C15 H15 126.2 . . ? C18 C19 C20 107.7(7) . . ? C18 C19 Fe1 68.6(4) . . ? C20 C19 Fe1 69.6(3) . . ? C18 C19 H19 126.2 . . ? C20 C19 H19 126.2 . . ? Fe1 C19 H19 127.2 . . ? C15 C14 C13 108.1(6) . . ? C15 C14 Fe1 69.6(4) . . ? C13 C14 Fe1 69.9(4) . . ? C15 C14 H14 126.0 . . ? C13 C14 H14 126.0 . . ? Fe1 C14 H14 126.1 . . ? C20 C16 C17 107.8(8) . . ? C20 C16 Fe1 70.0(4) . . ? C17 C16 Fe1 69.6(5) . . ? C20 C16 H16 126.1 . . ? C17 C16 H16 126.1 . . ? Fe1 C16 H16 125.9 . . ? C12 C11 C15 106.5(6) . . ? C12 C11 C1 128.9(7) . . ? C15 C11 C1 124.0(7) . . ? C12 C11 Fe1 68.6(4) . . ? C15 C11 Fe1 69.2(4) . . ? C1 C11 Fe1 120.1(4) . . ? C14 C13 C12 108.1(7) . . ? C14 C13 Fe1 69.6(4) . . ? C12 C13 Fe1 68.6(4) . . ? C14 C13 H13 125.9 . . ? C12 C13 H13 125.9 . . ? Fe1 C13 H13 127.5 . . ? C13 C12 C11 108.5(7) . . ? C13 C12 Fe1 70.8(4) . . ? C11 C12 Fe1 70.2(4) . . ? C13 C12 H12 125.8 . . ? C11 C12 H12 125.8 . . ? Fe1 C12 H12 124.8 . . ? C18 C17 C16 107.5(8) . . ? C18 C17 Fe1 69.3(5) . . ? C16 C17 Fe1 70.0(5) . . ? C18 C17 H17 126.3 . . ? C16 C17 H17 126.3 . . ? Fe1 C17 H17 126.0 . . ? C19 C18 C17 108.8(8) . . ? C19 C18 Fe1 71.2(4) . . ? C17 C18 Fe1 70.3(5) . . ? C19 C18 H18 125.6 . . ? C17 C18 H18 125.6 . . ? Fe1 C18 H18 124.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 O3 C4 C5 176.7(6) . . . . ? C3 O3 C4 C9 -2.8(9) . . . . ? C3 C2 C10 C9 2.1(9) . . . . ? C1 C2 C10 C9 -175.0(6) . . . . ? C10 C2 C1 O1 124.9(7) . . . . ? C3 C2 C1 O1 -52.4(8) . . . . ? C10 C2 C1 C11 -55.8(8) . . . . ? C3 C2 C1 C11 126.9(6) . . . . ? C5 C4 C9 C8 0.1(10) . . . . ? O3 C4 C9 C8 179.5(6) . . . . ? C5 C4 C9 C10 -179.8(6) . . . . ? O3 C4 C9 C10 -0.3(9) . . . . ? C2 C10 C9 C4 0.5(9) . . . . ? C2 C10 C9 C8 -179.3(6) . . . . ? C18 Fe1 C20 C19 37.3(5) . . . . ? C12 Fe1 C20 C19 157.6(8) . . . . ? C17 Fe1 C20 C19 81.2(5) . . . . ? C15 Fe1 C20 C19 -119.7(5) . . . . ? C16 Fe1 C20 C19 119.0(7) . . . . ? C14 Fe1 C20 C19 -77.2(6) . . . . ? C11 Fe1 C20 C19 -163.5(5) . . . . ? C13 Fe1 C20 C19 -39.6(11) . . . . ? C18 Fe1 C20 C16 -81.7(5) . . . . ? C12 Fe1 C20 C16 38.6(11) . . . . ? C17 Fe1 C20 C16 -37.8(5) . . . . ? C15 Fe1 C20 C16 121.3(5) . . . . ? C14 Fe1 C20 C16 163.8(5) . . . . ? C11 Fe1 C20 C16 77.5(5) . . . . ? C13 Fe1 C20 C16 -158.6(9) . . . . ? C19 Fe1 C20 C16 -119.0(7) . . . . ? O3 C4 C5 C6 -178.7(6) . . . . ? C9 C4 C5 C6 0.7(10) . . . . ? C4 O3 C3 O2 -173.0(6) . . . . ? C4 O3 C3 C2 5.2(8) . . . . ? C10 C2 C3 O2 173.1(7) . . . . ? C1 C2 C3 O2 -9.5(10) . . . . ? C10 C2 C3 O3 -4.9(9) . . . . ? C1 C2 C3 O3 172.5(5) . . . . ? C4 C5 C6 C7 -0.7(11) . . . . ? C4 C9 C8 C7 -0.9(10) . . . . ? C10 C9 C8 C7 178.9(6) . . . . ? C9 C8 C7 C6 0.9(11) . . . . ? C5 C6 C7 C8 -0.1(11) . . . . ? C18 Fe1 C15 C14 40.9(10) . . . . ? C12 Fe1 C15 C14 -81.6(4) . . . . ? C17 Fe1 C15 C14 -160.4(9) . . . . ? C16 Fe1 C15 C14 162.5(5) . . . . ? C20 Fe1 C15 C14 119.9(5) . . . . ? C11 Fe1 C15 C14 -120.0(6) . . . . ? C13 Fe1 C15 C14 -37.8(4) . . . . ? C19 Fe1 C15 C14 77.7(5) . . . . ? C18 Fe1 C15 C11 160.9(7) . . . . ? C12 Fe1 C15 C11 38.4(4) . . . . ? C17 Fe1 C15 C11 -40.4(11) . . . . ? C16 Fe1 C15 C11 -77.5(5) . . . . ? C20 Fe1 C15 C11 -120.1(5) . . . . ? C14 Fe1 C15 C11 120.0(6) . . . . ? C13 Fe1 C15 C11 82.2(4) . . . . ? C19 Fe1 C15 C11 -162.4(4) . . . . ? C16 C20 C19 C18 1.5(8) . . . . ? Fe1 C20 C19 C18 -58.2(5) . . . . ? C16 C20 C19 Fe1 59.7(5) . . . . ? C12 Fe1 C19 C18 -40.2(10) . . . . ? C17 Fe1 C19 C18 37.8(5) . . . . ? C15 Fe1 C19 C18 -160.1(5) . . . . ? C16 Fe1 C19 C18 81.8(6) . . . . ? C20 Fe1 C19 C18 119.6(7) . . . . ? C14 Fe1 C19 C18 -118.5(6) . . . . ? C11 Fe1 C19 C18 163.5(7) . . . . ? C13 Fe1 C19 C18 -76.1(6) . . . . ? C18 Fe1 C19 C20 -119.6(7) . . . . ? C12 Fe1 C19 C20 -159.8(7) . . . . ? C17 Fe1 C19 C20 -81.7(5) . . . . ? C15 Fe1 C19 C20 80.3(5) . . . . ? C16 Fe1 C19 C20 -37.8(5) . . . . ? C14 Fe1 C19 C20 121.9(5) . . . . ? C11 Fe1 C19 C20 43.9(10) . . . . ? C13 Fe1 C19 C20 164.3(5) . . . . ? C11 C15 C14 C13 0.5(8) . . . . ? Fe1 C15 C14 C13 59.5(5) . . . . ? C11 C15 C14 Fe1 -59.0(5) . . . . ? C18 Fe1 C14 C15 -163.5(4) . . . . ? C12 Fe1 C14 C15 82.1(4) . . . . ? C17 Fe1 C14 C15 162.9(7) . . . . ? C16 Fe1 C14 C15 -47.6(10) . . . . ? C20 Fe1 C14 C15 -80.3(5) . . . . ? C11 Fe1 C14 C15 37.8(4) . . . . ? C13 Fe1 C14 C15 119.2(6) . . . . ? C19 Fe1 C14 C15 -121.5(4) . . . . ? C18 Fe1 C14 C13 77.2(5) . . . . ? C12 Fe1 C14 C13 -37.2(4) . . . . ? C17 Fe1 C14 C13 43.7(9) . . . . ? C15 Fe1 C14 C13 -119.2(6) . . . . ? C16 Fe1 C14 C13 -166.8(7) . . . . ? C20 Fe1 C14 C13 160.4(4) . . . . ? C11 Fe1 C14 C13 -81.5(4) . . . . ? C19 Fe1 C14 C13 119.2(5) . . . . ? C19 C20 C16 C17 -0.7(9) . . . . ? Fe1 C20 C16 C17 59.5(6) . . . . ? C19 C20 C16 Fe1 -60.2(5) . . . . ? C18 Fe1 C16 C20 81.0(4) . . . . ? C12 Fe1 C16 C20 -165.2(4) . . . . ? C17 Fe1 C16 C20 118.9(7) . . . . ? C15 Fe1 C16 C20 -79.3(5) . . . . ? C14 Fe1 C16 C20 -43.7(10) . . . . ? C11 Fe1 C16 C20 -122.0(5) . . . . ? C13 Fe1 C16 C20 159.6(7) . . . . ? C19 Fe1 C16 C20 37.4(4) . . . . ? C18 Fe1 C16 C17 -37.9(5) . . . . ? C12 Fe1 C16 C17 75.9(6) . . . . ? C15 Fe1 C16 C17 161.8(5) . . . . ? C20 Fe1 C16 C17 -118.9(7) . . . . ? C14 Fe1 C16 C17 -162.6(7) . . . . ? C11 Fe1 C16 C17 119.1(5) . . . . ? C13 Fe1 C16 C17 40.8(10) . . . . ? C19 Fe1 C16 C17 -81.5(5) . . . . ? C14 C15 C11 C12 0.7(7) . . . . ? Fe1 C15 C11 C12 -58.8(4) . . . . ? C14 C15 C11 C1 172.5(6) . . . . ? Fe1 C15 C11 C1 113.0(6) . . . . ? C14 C15 C11 Fe1 59.5(5) . . . . ? O1 C1 C11 C12 174.8(6) . . . . ? C2 C1 C11 C12 -4.4(9) . . . . ? O1 C1 C11 C15 4.9(10) . . . . ? C2 C1 C11 C15 -174.3(5) . . . . ? O1 C1 C11 Fe1 89.0(8) . . . . ? C2 C1 C11 Fe1 -90.3(6) . . . . ? C18 Fe1 C11 C12 -42.9(10) . . . . ? C17 Fe1 C11 C12 -76.7(6) . . . . ? C15 Fe1 C11 C12 118.3(6) . . . . ? C16 Fe1 C11 C12 -119.0(5) . . . . ? C20 Fe1 C11 C12 -160.8(4) . . . . ? C14 Fe1 C11 C12 81.5(4) . . . . ? C13 Fe1 C11 C12 37.8(4) . . . . ? C19 Fe1 C11 C12 166.5(8) . . . . ? C18 Fe1 C11 C15 -161.2(8) . . . . ? C12 Fe1 C11 C15 -118.3(6) . . . . ? C17 Fe1 C11 C15 165.0(5) . . . . ? C16 Fe1 C11 C15 122.7(5) . . . . ? C20 Fe1 C11 C15 80.9(5) . . . . ? C14 Fe1 C11 C15 -36.8(4) . . . . ? C13 Fe1 C11 C15 -80.5(4) . . . . ? C19 Fe1 C11 C15 48.2(10) . . . . ? C18 Fe1 C11 C1 80.7(10) . . . . ? C12 Fe1 C11 C1 123.6(8) . . . . ? C17 Fe1 C11 C1 46.9(7) . . . . ? C15 Fe1 C11 C1 -118.1(7) . . . . ? C16 Fe1 C11 C1 4.6(7) . . . . ? C20 Fe1 C11 C1 -37.2(7) . . . . ? C14 Fe1 C11 C1 -154.9(7) . . . . ? C13 Fe1 C11 C1 161.4(7) . . . . ? C19 Fe1 C11 C1 -69.9(10) . . . . ? C15 C14 C13 C12 -1.5(8) . . . . ? Fe1 C14 C13 C12 57.9(5) . . . . ? C15 C14 C13 Fe1 -59.3(5) . . . . ? C18 Fe1 C13 C14 -120.6(5) . . . . ? C12 Fe1 C13 C14 120.2(7) . . . . ? C17 Fe1 C13 C14 -162.0(5) . . . . ? C15 Fe1 C13 C14 37.4(4) . . . . ? C16 Fe1 C13 C14 168.3(7) . . . . ? C20 Fe1 C13 C14 -50.8(11) . . . . ? C11 Fe1 C13 C14 81.9(5) . . . . ? C19 Fe1 C13 C14 -79.9(6) . . . . ? C18 Fe1 C13 C12 119.2(5) . . . . ? C17 Fe1 C13 C12 77.9(6) . . . . ? C15 Fe1 C13 C12 -82.8(5) . . . . ? C16 Fe1 C13 C12 48.1(10) . . . . ? C20 Fe1 C13 C12 -171.0(8) . . . . ? C14 Fe1 C13 C12 -120.2(7) . . . . ? C11 Fe1 C13 C12 -38.3(4) . . . . ? C19 Fe1 C13 C12 159.9(5) . . . . ? C14 C13 C12 C11 1.9(8) . . . . ? Fe1 C13 C12 C11 60.4(5) . . . . ? C14 C13 C12 Fe1 -58.5(5) . . . . ? C15 C11 C12 C13 -1.6(7) . . . . ? C1 C11 C12 C13 -172.9(6) . . . . ? Fe1 C11 C12 C13 -60.8(5) . . . . ? C15 C11 C12 Fe1 59.1(4) . . . . ? C1 C11 C12 Fe1 -112.1(6) . . . . ? C18 Fe1 C12 C13 -78.4(6) . . . . ? C17 Fe1 C12 C13 -119.7(6) . . . . ? C15 Fe1 C12 C13 80.3(5) . . . . ? C16 Fe1 C12 C13 -160.7(6) . . . . ? C20 Fe1 C12 C13 170.6(8) . . . . ? C14 Fe1 C12 C13 37.1(5) . . . . ? C11 Fe1 C12 C13 118.8(7) . . . . ? C19 Fe1 C12 C13 -49.3(10) . . . . ? C18 Fe1 C12 C11 162.8(5) . . . . ? C17 Fe1 C12 C11 121.5(5) . . . . ? C15 Fe1 C12 C11 -38.5(4) . . . . ? C16 Fe1 C12 C11 80.5(5) . . . . ? C20 Fe1 C12 C11 51.9(10) . . . . ? C14 Fe1 C12 C11 -81.7(4) . . . . ? C13 Fe1 C12 C11 -118.8(7) . . . . ? C19 Fe1 C12 C11 -168.1(7) . . . . ? C20 C16 C17 C18 -0.3(9) . . . . ? Fe1 C16 C17 C18 59.4(6) . . . . ? C20 C16 C17 Fe1 -59.8(5) . . . . ? C12 Fe1 C17 C18 119.5(5) . . . . ? C15 Fe1 C17 C18 -168.1(7) . . . . ? C16 Fe1 C17 C18 -118.6(8) . . . . ? C20 Fe1 C17 C18 -80.9(5) . . . . ? C14 Fe1 C17 C18 46.3(10) . . . . ? C11 Fe1 C17 C18 161.4(5) . . . . ? C13 Fe1 C17 C18 78.0(6) . . . . ? C19 Fe1 C17 C18 -37.6(5) . . . . ? C18 Fe1 C17 C16 118.6(8) . . . . ? C12 Fe1 C17 C16 -121.8(5) . . . . ? C15 Fe1 C17 C16 -49.5(11) . . . . ? C20 Fe1 C17 C16 37.7(5) . . . . ? C14 Fe1 C17 C16 164.9(6) . . . . ? C11 Fe1 C17 C16 -80.0(6) . . . . ? C13 Fe1 C17 C16 -163.4(5) . . . . ? C19 Fe1 C17 C16 81.0(5) . . . . ? C20 C19 C18 C17 -1.7(9) . . . . ? Fe1 C19 C18 C17 -60.6(5) . . . . ? C20 C19 C18 Fe1 58.8(5) . . . . ? C16 C17 C18 C19 1.3(9) . . . . ? Fe1 C17 C18 C19 61.1(5) . . . . ? C16 C17 C18 Fe1 -59.9(6) . . . . ? C12 Fe1 C18 C19 163.3(5) . . . . ? C17 Fe1 C18 C19 -118.9(8) . . . . ? C15 Fe1 C18 C19 50.2(11) . . . . ? C16 Fe1 C18 C19 -80.9(5) . . . . ? C20 Fe1 C18 C19 -37.1(4) . . . . ? C14 Fe1 C18 C19 80.2(6) . . . . ? C11 Fe1 C18 C19 -165.1(7) . . . . ? C13 Fe1 C18 C19 121.6(5) . . . . ? C12 Fe1 C18 C17 -77.9(6) . . . . ? C15 Fe1 C18 C17 169.1(7) . . . . ? C16 Fe1 C18 C17 38.0(5) . . . . ? C20 Fe1 C18 C17 81.7(5) . . . . ? C14 Fe1 C18 C17 -160.9(5) . . . . ? C11 Fe1 C18 C17 -46.3(11) . . . . ? C13 Fe1 C18 C17 -119.5(6) . . . . ? C19 Fe1 C18 C17 118.9(8) . . . . ? _diffrn_measured_fraction_theta_max 0.856 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.326 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.080