# Electronic Supplementary Material (ESI) for Chemical Communications # 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_wp91ltb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H24 F3 Fe I2 N4 O6 S' _chemical_formula_weight 983.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.2488(5) _cell_length_b 12.3956(4) _cell_length_c 12.8192(9) _cell_angle_alpha 70.108(5) _cell_angle_beta 87.581(6) _cell_angle_gamma 68.745(5) _cell_volume 1698.40(15) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 8269 _cell_measurement_theta_min 6.6 _cell_measurement_theta_max 70.5 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.923 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 958 _exptl_absorpt_coefficient_mu 19.012 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.57 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rigaku MM007 rotating anode' _diffrn_radiation_monochromator 'Rigaku VariMax-HF Confocal Optical System' _diffrn_measurement_device_type 'Rigaku Spider' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19123 _diffrn_reflns_av_R_equivalents 0.0875 _diffrn_reflns_av_sigmaI/netI 0.1051 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 6.61 _diffrn_reflns_theta_max 72.08 _reflns_number_total 6290 _reflns_number_gt 4155 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_data_reduction 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _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. One restraint commeand, 'SIMU C28 C29', was used during the refinement to restrain the atomic displacement parameters of these atoms to be similar. ; _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^)+(0.1600P)^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 ? _refine_ls_number_reflns 6290 _refine_ls_number_parameters 462 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1160 _refine_ls_R_factor_gt 0.0969 _refine_ls_wR_factor_ref 0.3105 _refine_ls_wR_factor_gt 0.2574 _refine_ls_goodness_of_fit_ref 1.221 _refine_ls_restrained_S_all 1.221 _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 1.12029(16) 0.21563(16) -0.03950(15) 0.0412(5) Uani 1 1 d . . . I1 I 0.96837(8) 0.35636(8) 0.49094(7) 0.0573(3) Uani 1 1 d . . . I2 I 0.63274(8) 0.26728(9) -0.41946(7) 0.0601(3) Uani 1 1 d . . . N1 N 1.1423(8) 0.3511(9) -0.0077(7) 0.041(2) Uani 1 1 d . . . N2 N 1.1972(8) 0.2703(9) -0.1715(8) 0.046(2) Uani 1 1 d . . . N20 N 1.2782(9) 0.0906(9) 0.0357(7) 0.043(2) Uani 1 1 d . . . N21 N 1.1094(9) 0.0779(10) -0.0735(8) 0.046(2) Uani 1 1 d . . . C1 C 1.0350(10) 0.2090(11) 0.1751(9) 0.043(3) Uani 1 1 d . . . C2 C 0.9844(11) 0.1562(11) 0.2682(11) 0.050(3) Uani 1 1 d . . . H2 H 0.9631 0.0891 0.2704 0.060 Uiso 1 1 calc R . . C3 C 0.9640(12) 0.1969(12) 0.3571(11) 0.055(3) Uani 1 1 d . . . H3 H 0.9329 0.1559 0.4208 0.066 Uiso 1 1 calc R . . C4 C 0.9900(11) 0.3010(13) 0.3523(10) 0.051(3) Uani 1 1 d . . . C5 C 1.0351(11) 0.3576(12) 0.2611(11) 0.049(3) Uani 1 1 d . . . H5 H 1.0513 0.4279 0.2584 0.059 Uiso 1 1 calc R . . C6 C 1.0589(10) 0.3158(12) 0.1696(10) 0.044(3) Uani 1 1 d . . . C7 C 1.1091(10) 0.3809(10) 0.0789(8) 0.038(2) Uani 1 1 d . . . H7 H 1.1188 0.4521 0.0827 0.046 Uiso 1 1 calc R . . C8 C 1.1998(10) 0.4154(11) -0.0901(9) 0.043(3) Uani 1 1 d . . . C9 C 1.2320(11) 0.5105(12) -0.0868(10) 0.051(3) Uani 1 1 d . . . H9 H 1.2161 0.5394 -0.0259 0.061 Uiso 1 1 calc R . . C10 C 1.2883(12) 0.5622(12) -0.1753(11) 0.057(3) Uani 1 1 d . . . H10 H 1.3089 0.6287 -0.1739 0.068 Uiso 1 1 calc R . . C11 C 1.3160(12) 0.5233(14) -0.2647(11) 0.060(4) Uani 1 1 d . . . H11 H 1.3564 0.5603 -0.3223 0.071 Uiso 1 1 calc R . . C12 C 1.2825(11) 0.4254(13) -0.2688(11) 0.053(3) Uani 1 1 d . . . C13 C 1.2243(10) 0.3704(10) -0.1772(10) 0.042(3) Uani 1 1 d . . . C14 C 1.3007(11) 0.3785(10) -0.3553(8) 0.045(3) Uani 1 1 d . . . H14 H 1.3359 0.4140 -0.4187 0.054 Uiso 1 1 calc R . . C15 C 1.2681(10) 0.2803(10) -0.3504(10) 0.046(3) Uani 1 1 d . . . H15 H 1.2792 0.2496 -0.4102 0.055 Uiso 1 1 calc R . . C16 C 1.2186(10) 0.2278(11) -0.2551(8) 0.042(3) Uani 1 1 d . . . H16 H 1.1995 0.1586 -0.2502 0.050 Uiso 1 1 calc R . . C20 C 0.9047(10) 0.3072(11) -0.1760(9) 0.040(3) Uani 1 1 d . . . C21 C 0.8052(11) 0.4094(11) -0.2358(9) 0.045(3) Uani 1 1 d . . . H21 H 0.7914 0.4879 -0.2308 0.055 Uiso 1 1 calc R . . C22 C 0.7272(11) 0.3974(11) -0.3017(9) 0.045(3) Uani 1 1 d . . . H22 H 0.6597 0.4674 -0.3401 0.055 Uiso 1 1 calc R . . C23 C 0.7458(11) 0.2852(12) -0.3128(9) 0.046(3) Uani 1 1 d . . . C24 C 0.8376(11) 0.1873(11) -0.2582(10) 0.043(3) Uani 1 1 d . . . H24 H 0.8484 0.1096 -0.2635 0.052 Uiso 1 1 calc R . . C25 C 0.9224(10) 0.1968(10) -0.1900(9) 0.038(2) Uani 1 1 d . . . C26 C 1.0206(11) 0.0845(11) -0.1322(9) 0.048(3) Uani 1 1 d . . . H26 H 1.0207 0.0097 -0.1372 0.057 Uiso 1 1 calc R . . C27 C 1.2065(10) -0.0347(10) -0.0261(10) 0.042(3) Uani 1 1 d . . . C28 C 1.2218(10) -0.1442(9) -0.0367(8) 0.037(3) Uani 1 1 d U . . H28 H 1.1650 -0.1507 -0.0800 0.045 Uiso 1 1 calc R . . C29 C 1.3229(12) -0.2483(13) 0.0173(10) 0.055(3) Uani 1 1 d U . . H29 H 1.3298 -0.3261 0.0145 0.066 Uiso 1 1 calc R . . C30 C 1.4144(12) -0.2419(12) 0.0751(10) 0.050(3) Uani 1 1 d . . . H30 H 1.4834 -0.3126 0.1081 0.060 Uiso 1 1 calc R . . C31 C 1.3993(11) -0.1262(11) 0.0821(11) 0.048(3) Uani 1 1 d . . . C32 C 1.2927(11) -0.0189(12) 0.0261(10) 0.045(3) Uani 1 1 d . . . C33 C 1.4833(13) -0.1098(14) 0.1412(13) 0.063(4) Uani 1 1 d . . . H33 H 1.5528 -0.1774 0.1791 0.075 Uiso 1 1 calc R . . C34 C 1.4618(11) 0.0065(11) 0.1423(9) 0.046(3) Uani 1 1 d . . . H34 H 1.5177 0.0203 0.1802 0.055 Uiso 1 1 calc R . . C35 C 1.3549(10) 0.1078(11) 0.0864(10) 0.044(3) Uani 1 1 d . . . H35 H 1.3413 0.1880 0.0871 0.053 Uiso 1 1 calc R . . C100 C 0.3952(14) 0.1985(13) 0.3626(11) 0.062(4) Uani 1 1 d . . . C200 C 0.7834(15) -0.0062(14) 0.4107(10) 0.082(5) Uani 1 1 d . . . H20A H 0.8639 -0.0528 0.4463 0.123 Uiso 1 1 calc R . . H20B H 0.7345 -0.0551 0.4412 0.123 Uiso 1 1 calc R . . H20C H 0.7512 0.0717 0.4251 0.123 Uiso 1 1 calc R . . O1 O 1.0543(7) 0.1625(7) 0.0938(7) 0.048(2) Uani 1 1 d . . . O20 O 0.9749(7) 0.3308(8) -0.1163(7) 0.048(2) Uani 1 1 d . . . O100 O 0.4893(8) 0.3578(9) 0.2920(9) 0.077(3) Uani 1 1 d . . . O101 O 0.5551(9) 0.1825(10) 0.2291(9) 0.074(3) Uani 1 1 d . . . O102 O 0.3611(8) 0.3435(8) 0.1609(6) 0.058(2) Uani 1 1 d . . . O200 O 0.7841(9) 0.0182(10) 0.2985(8) 0.070(3) Uani 1 1 d . . . H200 H 0.7165 0.0344 0.2712 0.105 Uiso 1 1 calc R . . F1 F 0.3635(9) 0.1119(9) 0.3423(8) 0.099(3) Uani 1 1 d . . . F2 F 0.2968(8) 0.2743(9) 0.3899(7) 0.086(3) Uani 1 1 d . . . F3 F 0.4680(9) 0.1375(9) 0.4581(8) 0.092(3) Uani 1 1 d . . . S1 S 0.4574(3) 0.2789(3) 0.2493(3) 0.0589(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0528(11) 0.0472(11) 0.0440(11) -0.0319(9) 0.0079(8) -0.0270(9) I1 0.0697(6) 0.0737(7) 0.0518(6) -0.0441(5) 0.0102(4) -0.0322(5) I2 0.0635(6) 0.0760(7) 0.0618(6) -0.0393(5) -0.0004(4) -0.0346(5) N1 0.043(5) 0.054(6) 0.036(5) -0.023(4) -0.004(4) -0.020(5) N2 0.054(6) 0.050(6) 0.049(6) -0.029(5) 0.006(5) -0.027(5) N20 0.066(6) 0.058(6) 0.028(5) -0.027(5) 0.012(4) -0.039(5) N21 0.057(6) 0.071(7) 0.035(5) -0.038(5) 0.013(5) -0.036(6) C1 0.054(7) 0.048(7) 0.042(7) -0.027(5) 0.003(5) -0.025(6) C2 0.059(8) 0.049(7) 0.064(8) -0.041(6) 0.017(6) -0.025(6) C3 0.074(9) 0.061(8) 0.055(8) -0.034(7) 0.022(7) -0.042(7) C4 0.063(8) 0.078(9) 0.040(7) -0.042(7) 0.012(6) -0.038(7) C5 0.058(7) 0.058(8) 0.058(8) -0.042(6) 0.007(6) -0.031(6) C6 0.048(7) 0.063(8) 0.043(7) -0.037(6) 0.007(5) -0.029(6) C7 0.056(7) 0.043(6) 0.024(5) -0.011(4) -0.008(5) -0.026(5) C8 0.060(7) 0.053(7) 0.039(6) -0.027(5) 0.017(5) -0.038(6) C9 0.062(8) 0.073(9) 0.039(7) -0.033(6) 0.007(6) -0.037(7) C10 0.075(9) 0.050(8) 0.068(9) -0.032(7) 0.006(7) -0.038(7) C11 0.072(9) 0.085(10) 0.050(8) -0.039(7) 0.018(7) -0.048(8) C12 0.047(7) 0.067(9) 0.061(8) -0.038(7) 0.010(6) -0.024(7) C13 0.041(6) 0.039(6) 0.055(7) -0.024(6) 0.009(5) -0.017(5) C14 0.077(8) 0.036(6) 0.021(5) -0.004(4) 0.012(5) -0.024(6) C15 0.044(7) 0.042(7) 0.045(7) -0.019(5) -0.005(5) -0.005(5) C16 0.047(7) 0.051(7) 0.023(5) -0.014(4) -0.013(4) -0.011(5) C20 0.044(6) 0.041(6) 0.040(6) -0.015(5) -0.001(5) -0.020(5) C21 0.063(8) 0.049(7) 0.027(6) -0.013(5) -0.006(5) -0.021(6) C22 0.057(7) 0.049(7) 0.031(6) -0.009(5) 0.002(5) -0.026(6) C23 0.059(7) 0.060(8) 0.029(6) -0.020(5) -0.006(5) -0.028(6) C24 0.056(7) 0.035(6) 0.048(7) -0.022(5) 0.005(6) -0.020(6) C25 0.045(6) 0.033(6) 0.035(6) -0.013(4) -0.006(5) -0.011(5) C26 0.074(9) 0.052(8) 0.042(7) -0.028(6) 0.018(6) -0.042(7) C27 0.047(7) 0.029(6) 0.049(7) -0.019(5) 0.000(5) -0.008(5) C28 0.055(7) 0.021(5) 0.018(5) 0.003(4) -0.020(4) 0.000(4) C29 0.081(9) 0.067(8) 0.047(7) -0.035(6) 0.015(6) -0.046(8) C30 0.052(7) 0.052(8) 0.043(7) -0.025(6) -0.004(6) -0.007(6) C31 0.054(7) 0.040(7) 0.063(8) -0.032(6) 0.001(6) -0.017(6) C32 0.059(7) 0.054(7) 0.040(7) -0.029(6) 0.011(6) -0.031(6) C33 0.065(9) 0.071(10) 0.080(10) -0.050(8) 0.023(8) -0.035(8) C34 0.069(8) 0.052(7) 0.027(6) -0.008(5) -0.010(5) -0.035(6) C35 0.052(7) 0.035(6) 0.050(7) -0.018(5) -0.006(5) -0.017(5) C100 0.085(11) 0.059(9) 0.041(7) -0.022(6) -0.012(7) -0.020(8) C200 0.108(12) 0.075(10) 0.022(6) 0.003(6) -0.033(7) -0.003(9) O1 0.060(5) 0.052(5) 0.058(5) -0.043(4) 0.011(4) -0.029(4) O20 0.052(5) 0.059(5) 0.054(5) -0.038(4) 0.004(4) -0.027(4) O100 0.080(7) 0.079(7) 0.107(9) -0.055(7) 0.007(6) -0.046(6) O101 0.070(6) 0.083(7) 0.086(7) -0.057(6) 0.019(6) -0.023(6) O102 0.066(6) 0.062(6) 0.037(5) -0.008(4) -0.022(4) -0.019(5) O200 0.074(7) 0.080(7) 0.071(7) -0.045(6) 0.006(5) -0.028(6) F1 0.139(9) 0.115(8) 0.097(7) -0.056(6) 0.036(6) -0.093(7) F2 0.081(6) 0.115(8) 0.080(6) -0.057(6) 0.026(5) -0.037(6) F3 0.101(7) 0.087(7) 0.070(6) -0.022(5) -0.011(5) -0.017(6) S1 0.061(2) 0.073(2) 0.070(2) -0.0476(19) 0.0162(17) -0.0361(19) _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 O1 1.874(8) . ? Fe1 O20 1.878(8) . ? Fe1 N2 1.939(10) . ? Fe1 N21 1.948(9) . ? Fe1 N1 1.965(9) . ? Fe1 N20 2.010(10) . ? I1 C4 2.088(10) . ? I2 C23 2.104(10) . ? N1 C7 1.291(13) . ? N1 C8 1.421(13) . ? N2 C16 1.324(13) . ? N2 C13 1.374(13) . ? N20 C35 1.281(13) . ? N20 C32 1.352(13) . ? N21 C26 1.312(14) . ? N21 C27 1.419(15) . ? C1 O1 1.328(12) . ? C1 C2 1.390(16) . ? C1 C6 1.435(14) . ? C2 C3 1.375(15) . ? C2 H2 0.9500 . ? C3 C4 1.418(15) . ? C3 H3 0.9500 . ? C4 C5 1.354(16) . ? C5 C6 1.416(14) . ? C5 H5 0.9500 . ? C6 C7 1.428(15) . ? C7 H7 0.9500 . ? C8 C9 1.385(15) . ? C8 C13 1.386(14) . ? C9 C10 1.392(17) . ? C9 H9 0.9500 . ? C10 C11 1.373(16) . ? C10 H10 0.9500 . ? C11 C12 1.431(17) . ? C11 H11 0.9500 . ? C12 C14 1.394(15) . ? C12 C13 1.446(16) . ? C14 C15 1.394(16) . ? C14 H14 0.9500 . ? C15 C16 1.403(16) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C20 O20 1.341(12) . ? C20 C25 1.378(14) . ? C20 C21 1.406(15) . ? C21 C22 1.381(14) . ? C21 H21 0.9500 . ? C22 C23 1.381(16) . ? C22 H22 0.9500 . ? C23 C24 1.314(16) . ? C24 C25 1.446(14) . ? C24 H24 0.9500 . ? C25 C26 1.447(16) . ? C26 H26 0.9500 . ? C27 C28 1.354(14) . ? C27 C32 1.378(15) . ? C28 C29 1.408(17) . ? C28 H28 0.9500 . ? C29 C30 1.409(16) . ? C29 H29 0.9500 . ? C30 C31 1.413(16) . ? C30 H30 0.9500 . ? C31 C33 1.413(17) . ? C31 C32 1.470(18) . ? C33 C34 1.373(17) . ? C33 H33 0.9500 . ? C34 C35 1.442(16) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C100 F2 1.351(16) . ? C100 F3 1.356(14) . ? C100 F1 1.368(15) . ? C100 S1 1.776(15) . ? C200 O200 1.366(14) . ? C200 H20A 0.9800 . ? C200 H20B 0.9800 . ? C200 H20C 0.9800 . ? O100 S1 1.439(8) . ? O101 S1 1.440(9) . ? O102 S1 1.459(8) . ? O200 H200 0.8400 . ? 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 O1 Fe1 O20 93.6(4) . . ? O1 Fe1 N2 176.2(3) . . ? O20 Fe1 N2 89.3(4) . . ? O1 Fe1 N21 88.0(3) . . ? O20 Fe1 N21 95.3(4) . . ? N2 Fe1 N21 94.3(4) . . ? O1 Fe1 N1 94.6(3) . . ? O20 Fe1 N1 87.5(3) . . ? N2 Fe1 N1 83.0(4) . . ? N21 Fe1 N1 176.2(4) . . ? O1 Fe1 N20 88.7(3) . . ? O20 Fe1 N20 177.1(3) . . ? N2 Fe1 N20 88.5(4) . . ? N21 Fe1 N20 83.1(4) . . ? N1 Fe1 N20 94.1(4) . . ? C7 N1 C8 121.9(9) . . ? C7 N1 Fe1 124.7(8) . . ? C8 N1 Fe1 113.5(7) . . ? C16 N2 C13 119.3(10) . . ? C16 N2 Fe1 128.0(8) . . ? C13 N2 Fe1 112.6(7) . . ? C35 N20 C32 123.7(11) . . ? C35 N20 Fe1 127.1(8) . . ? C32 N20 Fe1 109.2(8) . . ? C26 N21 C27 121.4(9) . . ? C26 N21 Fe1 124.7(9) . . ? C27 N21 Fe1 113.9(7) . . ? O1 C1 C2 119.2(10) . . ? O1 C1 C6 123.0(10) . . ? C2 C1 C6 117.8(10) . . ? C3 C2 C1 122.9(11) . . ? C3 C2 H2 118.6 . . ? C1 C2 H2 118.6 . . ? C2 C3 C4 119.1(11) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 119.6(10) . . ? C5 C4 I1 121.2(8) . . ? C3 C4 I1 119.1(9) . . ? C4 C5 C6 122.3(10) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C7 117.5(10) . . ? C5 C6 C1 118.3(10) . . ? C7 C6 C1 124.2(9) . . ? N1 C7 C6 125.6(10) . . ? N1 C7 H7 117.2 . . ? C6 C7 H7 117.2 . . ? C9 C8 C13 121.8(10) . . ? C9 C8 N1 126.1(10) . . ? C13 C8 N1 112.1(9) . . ? C8 C9 C10 117.9(10) . . ? C8 C9 H9 121.0 . . ? C10 C9 H9 121.0 . . ? C11 C10 C9 124.1(11) . . ? C11 C10 H10 118.0 . . ? C9 C10 H10 118.0 . . ? C10 C11 C12 118.2(12) . . ? C10 C11 H11 120.9 . . ? C12 C11 H11 120.9 . . ? C14 C12 C11 125.1(12) . . ? C14 C12 C13 116.5(11) . . ? C11 C12 C13 118.4(11) . . ? N2 C13 C8 118.8(10) . . ? N2 C13 C12 121.5(10) . . ? C8 C13 C12 119.6(10) . . ? C15 C14 C12 121.0(11) . . ? C15 C14 H14 119.5 . . ? C12 C14 H14 119.5 . . ? C14 C15 C16 118.4(10) . . ? C14 C15 H15 120.8 . . ? C16 C15 H15 120.8 . . ? N2 C16 C15 123.0(11) . . ? N2 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? O20 C20 C25 127.5(11) . . ? O20 C20 C21 115.5(10) . . ? C25 C20 C21 116.8(10) . . ? C22 C21 C20 121.0(11) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C23 121.0(11) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 119.9(10) . . ? C24 C23 I2 118.6(9) . . ? C22 C23 I2 121.6(9) . . ? C23 C24 C25 120.6(10) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C20 C25 C24 120.5(10) . . ? C20 C25 C26 122.3(10) . . ? C24 C25 C26 117.0(9) . . ? N21 C26 C25 125.0(10) . . ? N21 C26 H26 117.5 . . ? C25 C26 H26 117.5 . . ? C28 C27 C32 121.8(11) . . ? C28 C27 N21 126.3(10) . . ? C32 C27 N21 111.7(9) . . ? C27 C28 C29 119.2(10) . . ? C27 C28 H28 120.4 . . ? C29 C28 H28 120.4 . . ? C28 C29 C30 122.8(11) . . ? C28 C29 H29 118.6 . . ? C30 C29 H29 118.6 . . ? C29 C30 C31 117.3(12) . . ? C29 C30 H30 121.3 . . ? C31 C30 H30 121.3 . . ? C30 C31 C33 122.2(12) . . ? C30 C31 C32 119.0(11) . . ? C33 C31 C32 118.8(11) . . ? N20 C32 C27 122.0(12) . . ? N20 C32 C31 118.3(11) . . ? C27 C32 C31 119.5(10) . . ? C34 C33 C31 118.1(13) . . ? C34 C33 H33 120.9 . . ? C31 C33 H33 120.9 . . ? C33 C34 C35 120.4(11) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? N20 C35 C34 120.6(10) . . ? N20 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? F2 C100 F3 104.9(11) . . ? F2 C100 F1 105.6(12) . . ? F3 C100 F1 105.8(12) . . ? F2 C100 S1 112.7(10) . . ? F3 C100 S1 113.6(11) . . ? F1 C100 S1 113.4(9) . . ? O200 C200 H20A 109.5 . . ? O200 C200 H20B 109.5 . . ? H20A C200 H20B 109.5 . . ? O200 C200 H20C 109.5 . . ? H20A C200 H20C 109.5 . . ? H20B C200 H20C 109.5 . . ? C1 O1 Fe1 127.9(7) . . ? C20 O20 Fe1 124.6(7) . . ? C200 O200 H200 109.5 . . ? O100 S1 O101 114.9(6) . . ? O100 S1 O102 114.7(6) . . ? O101 S1 O102 114.5(6) . . ? O100 S1 C100 103.2(6) . . ? O101 S1 C100 104.0(7) . . ? O102 S1 C100 103.3(6) . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 72.08 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 1.649 _refine_diff_density_min -3.601 _refine_diff_density_rms 0.212 _database_code_depnum_ccdc_archive 'CCDC 929013' ####################################################################### # # 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_wp91-rt2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H24 F3 Fe I2 N4 O6 S' _chemical_formula_weight 983.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.7726(4) _cell_length_b 12.6918(4) _cell_length_c 13.3179(9) _cell_angle_alpha 69.437(5) _cell_angle_beta 85.020(6) _cell_angle_gamma 67.526(5) _cell_volume 1719.03(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3337 _cell_measurement_theta_min 6.7 _cell_measurement_theta_max 66.2 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.900 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 958 _exptl_absorpt_coefficient_mu 18.784 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.34 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rigaku MM007 rotating anode' _diffrn_radiation_monochromator 'Rigaku VariMax-HF Confocal Optical System' _diffrn_measurement_device_type 'Rigaku Spider' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24050 _diffrn_reflns_av_R_equivalents 0.0690 _diffrn_reflns_av_sigmaI/netI 0.0679 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 6.72 _diffrn_reflns_theta_max 66.54 _reflns_number_total 5900 _reflns_number_gt 3340 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_data_reduction 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _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. The atomic displacement parametsers of the methanol carbon atom are higher than average since it is somewhat free to move within a small cavity in the lattice. The following restrains were applied during the refinement to ensure that the atomic displacement parameters of its constituent atoms were reasonable: ISOR O200 SIMU O200 C200 ; _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^)+(0.1083P)^2^+0.8290P] 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 5900 _refine_ls_number_parameters 462 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.2375 _refine_ls_wR_factor_gt 0.1825 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.160 _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 0.09341(14) 0.22501(13) 0.96909(11) 0.0680(5) Uani 1 1 d . . . I1 I -0.01609(8) 0.34680(8) 1.50092(6) 0.1017(4) Uani 1 1 d . . . I2 I -0.36117(7) 0.26086(8) 0.56647(6) 0.1015(4) Uani 1 1 d . . . N1 N 0.1362(7) 0.3539(7) 1.0054(6) 0.067(2) Uani 1 1 d . . . N2 N 0.1859(7) 0.2950(7) 0.8310(5) 0.069(2) Uani 1 1 d . . . N20 N 0.2691(7) 0.0855(7) 1.0387(5) 0.0650(19) Uani 1 1 d . . . N21 N 0.0977(7) 0.0817(7) 0.9228(6) 0.0613(18) Uani 1 1 d . . . C1 C 0.0208(9) 0.2187(9) 1.1902(7) 0.071(3) Uani 1 1 d . . . C2 C -0.0262(10) 0.1628(10) 1.2847(8) 0.084(3) Uani 1 1 d . . . H2 H -0.0524 0.1014 1.2876 0.101 Uiso 1 1 calc R . . C3 C -0.0347(10) 0.1958(10) 1.3729(8) 0.085(3) Uani 1 1 d . . . H3 H -0.0643 0.1558 1.4357 0.102 Uiso 1 1 calc R . . C4 C 0.0014(9) 0.2902(9) 1.3682(8) 0.073(3) Uani 1 1 d . . . C5 C 0.0480(10) 0.3478(9) 1.2772(8) 0.078(3) Uani 1 1 d . . . H5 H 0.0714 0.4107 1.2753 0.094 Uiso 1 1 calc R . . C6 C 0.0607(9) 0.3123(8) 1.1859(7) 0.066(2) Uani 1 1 d . . . C7 C 0.1110(8) 0.3756(8) 1.0956(7) 0.066(2) Uani 1 1 d . . . H7 H 0.1280 0.4394 1.1009 0.079 Uiso 1 1 calc R . . C8 C 0.1968(9) 0.4173(9) 0.9267(7) 0.070(2) Uani 1 1 d . . . C9 C 0.2332(11) 0.5073(10) 0.9320(8) 0.093(4) Uani 1 1 d . . . H9 H 0.2198 0.5301 0.9925 0.112 Uiso 1 1 calc R . . C10 C 0.2912(11) 0.5637(10) 0.8434(9) 0.095(4) Uani 1 1 d . . . H10 H 0.3140 0.6248 0.8471 0.114 Uiso 1 1 calc R . . C11 C 0.3148(11) 0.5337(10) 0.7545(10) 0.098(4) Uani 1 1 d . . . H11 H 0.3545 0.5724 0.6991 0.118 Uiso 1 1 calc R . . C12 C 0.2794(10) 0.4439(9) 0.7460(8) 0.077(3) Uani 1 1 d . . . C13 C 0.2195(9) 0.3857(9) 0.8330(7) 0.070(2) Uani 1 1 d . . . C14 C 0.3016(11) 0.4032(10) 0.6579(8) 0.087(3) Uani 1 1 d . . . H14 H 0.3404 0.4383 0.5993 0.105 Uiso 1 1 calc R . . C15 C 0.2670(11) 0.3143(11) 0.6585(8) 0.090(3) Uani 1 1 d . . . H15 H 0.2809 0.2891 0.5993 0.108 Uiso 1 1 calc R . . C16 C 0.2102(11) 0.2583(11) 0.7466(7) 0.086(3) Uani 1 1 d . . . H16 H 0.1893 0.1948 0.7460 0.103 Uiso 1 1 calc R . . C20 C -0.1212(9) 0.3057(9) 0.8207(8) 0.069(2) Uani 1 1 d . . . C21 C -0.2238(9) 0.4019(9) 0.7625(8) 0.078(3) Uani 1 1 d . . . H21 H -0.2465 0.4771 0.7706 0.094 Uiso 1 1 calc R . . C22 C -0.2926(10) 0.3884(11) 0.6930(9) 0.089(3) Uani 1 1 d . . . H22 H -0.3617 0.4536 0.6549 0.107 Uiso 1 1 calc R . . C23 C -0.2570(12) 0.2729(12) 0.6797(8) 0.085(3) Uani 1 1 d . . . C24 C -0.1607(11) 0.1820(10) 0.7364(7) 0.076(3) Uani 1 1 d . . . H24 H -0.1396 0.1065 0.7294 0.092 Uiso 1 1 calc R . . C25 C -0.0890(10) 0.1934(10) 0.8059(8) 0.070(3) Uani 1 1 d . . . C26 C 0.0170(10) 0.0883(9) 0.8591(8) 0.072(3) Uani 1 1 d . . . H26 H 0.0287 0.0175 0.8463 0.086 Uiso 1 1 calc R . . C27 C 0.2036(10) -0.0294(9) 0.9650(7) 0.068(3) Uani 1 1 d . . . C28 C 0.2273(12) -0.1396(10) 0.9530(8) 0.079(3) Uani 1 1 d . . . H28 H 0.1722 -0.1460 0.9117 0.095 Uiso 1 1 calc R . . C29 C 0.3315(11) -0.2410(9) 1.0014(9) 0.086(3) Uani 1 1 d . . . H29 H 0.3427 -0.3143 0.9937 0.103 Uiso 1 1 calc R . . C30 C 0.4177(11) -0.2367(10) 1.0597(9) 0.085(3) Uani 1 1 d . . . H30 H 0.4889 -0.3047 1.0885 0.101 Uiso 1 1 calc R . . C31 C 0.3966(10) -0.1263(9) 1.0758(7) 0.070(3) Uani 1 1 d . . . C32 C 0.2887(9) -0.0216(8) 1.0269(7) 0.061(2) Uani 1 1 d . . . C33 C 0.4788(10) -0.1136(11) 1.1369(9) 0.088(3) Uani 1 1 d . . . H33 H 0.5491 -0.1803 1.1703 0.106 Uiso 1 1 calc R . . C34 C 0.4572(11) -0.0060(11) 1.1478(9) 0.088(3) Uani 1 1 d . . . H34 H 0.5123 0.0025 1.1874 0.106 Uiso 1 1 calc R . . C35 C 0.3497(11) 0.0926(11) 1.0980(8) 0.085(3) Uani 1 1 d . . . H35 H 0.3338 0.1665 1.1066 0.102 Uiso 1 1 calc R . . C100 C 0.3965(19) 0.182(2) 0.3863(14) 0.135(5) Uani 1 1 d . . . C200 C 0.801(5) 0.994(5) 0.408(3) 0.49(3) Uani 1 1 d U . . H20A H 0.7207 1.0402 0.4251 0.740 Uiso 1 1 calc R . . H20B H 0.8553 1.0356 0.4040 0.740 Uiso 1 1 calc R . . H20C H 0.8324 0.9152 0.4623 0.740 Uiso 1 1 calc R . . O1 O 0.0253(6) 0.1850(6) 1.1060(5) 0.0764(18) Uani 1 1 d . . . O20 O -0.0604(6) 0.3225(6) 0.8892(5) 0.0763(18) Uani 1 1 d . . . O100 O 0.4978(10) 0.3314(9) 0.3020(11) 0.175(5) Uani 1 1 d . . . O101 O 0.5593(10) 0.1520(12) 0.2526(10) 0.179(5) Uani 1 1 d . . . O102 O 0.3630(9) 0.3153(9) 0.1873(8) 0.130(3) Uani 1 1 d . . . O200 O 0.7933(11) 0.9827(13) 0.3152(10) 0.152(4) Uani 1 1 d U . . H200 H 0.7214 0.9975 0.3001 0.227 Uiso 1 1 calc R . . F1 F 0.3520(12) 0.1111(10) 0.3735(8) 0.195(5) Uani 1 1 d . . . F2 F 0.2988(12) 0.2763(14) 0.4054(8) 0.199(5) Uani 1 1 d . . . F3 F 0.4732(11) 0.1274(10) 0.4709(8) 0.186(4) Uani 1 1 d . . . S1 S 0.4611(4) 0.2553(3) 0.2690(3) 0.1044(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0890(12) 0.0735(10) 0.0617(8) -0.0341(7) 0.0034(8) -0.0419(9) I1 0.1249(8) 0.1347(8) 0.0752(5) -0.0587(5) 0.0157(5) -0.0617(6) I2 0.1047(7) 0.1321(8) 0.0863(5) -0.0420(5) -0.0099(4) -0.0572(6) N1 0.083(6) 0.073(5) 0.061(4) -0.033(4) 0.010(4) -0.038(4) N2 0.085(6) 0.087(5) 0.054(4) -0.035(4) 0.004(4) -0.041(5) N20 0.081(5) 0.069(5) 0.059(4) -0.030(4) -0.002(4) -0.035(4) N21 0.065(5) 0.071(5) 0.060(4) -0.030(4) 0.000(4) -0.031(4) C1 0.086(7) 0.082(7) 0.062(5) -0.040(5) 0.000(5) -0.036(6) C2 0.097(8) 0.108(8) 0.077(6) -0.046(6) 0.019(6) -0.061(7) C3 0.112(9) 0.097(8) 0.070(6) -0.039(6) 0.022(6) -0.058(7) C4 0.072(7) 0.095(7) 0.067(6) -0.049(5) 0.003(5) -0.027(6) C5 0.094(8) 0.089(7) 0.071(6) -0.038(6) 0.010(6) -0.047(6) C6 0.082(7) 0.074(6) 0.059(5) -0.032(5) 0.005(5) -0.039(5) C7 0.070(6) 0.064(6) 0.077(6) -0.033(5) 0.004(5) -0.032(5) C8 0.082(7) 0.078(6) 0.063(5) -0.025(5) 0.008(5) -0.044(6) C9 0.126(10) 0.123(9) 0.076(7) -0.055(7) 0.035(7) -0.081(8) C10 0.133(10) 0.093(8) 0.089(8) -0.037(7) 0.019(7) -0.071(8) C11 0.123(10) 0.103(9) 0.098(8) -0.037(7) 0.009(7) -0.071(8) C12 0.082(7) 0.090(7) 0.064(6) -0.028(5) 0.002(5) -0.038(6) C13 0.079(7) 0.076(6) 0.061(5) -0.022(5) -0.007(5) -0.035(6) C14 0.109(9) 0.105(8) 0.060(6) -0.020(6) 0.007(6) -0.062(8) C15 0.108(9) 0.121(9) 0.062(6) -0.040(6) 0.010(6) -0.059(8) C16 0.112(9) 0.119(9) 0.058(5) -0.042(6) 0.014(6) -0.066(8) C20 0.070(7) 0.067(6) 0.069(6) -0.020(5) -0.009(5) -0.026(5) C21 0.077(7) 0.076(7) 0.090(7) -0.037(6) 0.000(6) -0.030(6) C22 0.079(8) 0.101(9) 0.079(7) -0.019(6) -0.007(6) -0.035(7) C23 0.112(10) 0.123(10) 0.056(5) -0.042(6) 0.015(6) -0.076(8) C24 0.092(8) 0.088(7) 0.055(5) -0.017(5) -0.012(5) -0.045(7) C25 0.080(7) 0.079(7) 0.061(5) -0.020(5) -0.002(5) -0.042(6) C26 0.086(8) 0.073(7) 0.070(6) -0.029(5) 0.010(6) -0.042(6) C27 0.090(8) 0.086(7) 0.053(5) -0.034(5) 0.009(5) -0.053(6) C28 0.108(9) 0.087(7) 0.065(6) -0.034(5) 0.009(6) -0.053(7) C29 0.110(9) 0.051(6) 0.090(7) -0.023(6) -0.017(7) -0.020(6) C30 0.089(8) 0.073(7) 0.090(7) -0.034(6) 0.002(6) -0.024(6) C31 0.089(8) 0.071(6) 0.063(5) -0.034(5) 0.016(5) -0.035(6) C32 0.071(6) 0.062(6) 0.056(5) -0.019(4) 0.005(4) -0.030(5) C33 0.078(8) 0.092(8) 0.092(8) -0.037(6) -0.018(6) -0.020(6) C34 0.090(9) 0.086(8) 0.088(7) -0.028(6) -0.033(6) -0.026(7) C35 0.102(9) 0.096(8) 0.080(7) -0.049(6) -0.004(6) -0.043(7) C100 0.137(16) 0.176(17) 0.120(13) -0.067(13) 0.000(12) -0.072(14) C200 0.46(5) 0.50(5) 0.37(5) -0.09(4) 0.08(4) -0.09(4) O1 0.098(5) 0.083(4) 0.071(4) -0.035(3) 0.014(4) -0.051(4) O20 0.086(5) 0.082(4) 0.077(4) -0.041(4) -0.003(4) -0.035(4) O100 0.174(10) 0.145(8) 0.259(13) -0.079(9) -0.023(9) -0.100(8) O101 0.121(9) 0.226(13) 0.206(12) -0.143(11) 0.034(8) -0.026(9) O102 0.152(9) 0.130(7) 0.115(7) -0.037(6) -0.025(6) -0.057(7) O200 0.157(9) 0.163(9) 0.161(10) -0.085(8) 0.034(8) -0.067(9) F1 0.260(12) 0.188(9) 0.181(9) -0.021(7) -0.027(8) -0.162(10) F2 0.181(11) 0.298(15) 0.129(8) -0.099(9) 0.033(7) -0.083(10) F3 0.231(11) 0.191(9) 0.121(7) -0.008(6) -0.061(7) -0.091(8) S1 0.107(3) 0.115(3) 0.118(3) -0.055(2) 0.010(2) -0.057(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 O1 1.906(6) . ? Fe1 O20 1.907(7) . ? Fe1 N1 2.096(7) . ? Fe1 N21 2.098(7) . ? Fe1 N2 2.145(7) . ? Fe1 N20 2.157(8) . ? I1 C4 2.097(8) . ? I2 C23 2.104(10) . ? N1 C7 1.310(10) . ? N1 C8 1.403(10) . ? N2 C16 1.331(11) . ? N2 C13 1.362(11) . ? N20 C35 1.333(11) . ? N20 C32 1.353(10) . ? N21 C26 1.288(11) . ? N21 C27 1.442(12) . ? C1 O1 1.324(9) . ? C1 C2 1.394(13) . ? C1 C6 1.417(11) . ? C2 C3 1.364(12) . ? C2 H2 0.9300 . ? C3 C4 1.397(13) . ? C3 H3 0.9300 . ? C4 C5 1.369(13) . ? C5 C6 1.417(11) . ? C5 H5 0.9300 . ? C6 C7 1.416(12) . ? C7 H7 0.9300 . ? C8 C9 1.389(12) . ? C8 C13 1.415(12) . ? C9 C10 1.418(13) . ? C9 H9 0.9300 . ? C10 C11 1.343(14) . ? C10 H10 0.9300 . ? C11 C12 1.396(13) . ? C11 H11 0.9300 . ? C12 C14 1.407(13) . ? C12 C13 1.429(13) . ? C14 C15 1.336(14) . ? C14 H14 0.9300 . ? C15 C16 1.405(13) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C20 O20 1.325(10) . ? C20 C21 1.386(13) . ? C20 C25 1.409(13) . ? C21 C22 1.377(13) . ? C21 H21 0.9300 . ? C22 C23 1.433(15) . ? C22 H22 0.9300 . ? C23 C24 1.312(14) . ? C24 C25 1.383(12) . ? C24 H24 0.9300 . ? C25 C26 1.433(14) . ? C26 H26 0.9300 . ? C27 C28 1.382(13) . ? C27 C32 1.403(12) . ? C28 C29 1.386(14) . ? C28 H28 0.9300 . ? C29 C30 1.358(14) . ? C29 H29 0.9300 . ? C30 C31 1.417(13) . ? C30 H30 0.9300 . ? C31 C33 1.404(13) . ? C31 C32 1.431(13) . ? C33 C34 1.348(14) . ? C33 H33 0.9300 . ? C34 C35 1.400(14) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C100 F1 1.268(17) . ? C100 F3 1.309(17) . ? C100 F2 1.387(19) . ? C100 S1 1.787(18) . ? C200 O200 1.31(5) . ? C200 H20A 0.9600 . ? C200 H20B 0.9600 . ? C200 H20C 0.9600 . ? O100 S1 1.400(9) . ? O101 S1 1.450(10) . ? O102 S1 1.436(9) . ? O200 H200 0.8200 . ? 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 O1 Fe1 O20 95.9(3) . . ? O1 Fe1 N1 89.2(3) . . ? O20 Fe1 N1 101.9(3) . . ? O1 Fe1 N21 100.0(3) . . ? O20 Fe1 N21 88.6(3) . . ? N1 Fe1 N21 165.3(3) . . ? O1 Fe1 N2 165.8(3) . . ? O20 Fe1 N2 89.4(3) . . ? N1 Fe1 N2 76.8(3) . . ? N21 Fe1 N2 93.2(3) . . ? O1 Fe1 N20 89.5(3) . . ? O20 Fe1 N20 165.9(3) . . ? N1 Fe1 N20 91.2(3) . . ? N21 Fe1 N20 77.7(3) . . ? N2 Fe1 N20 88.4(3) . . ? C7 N1 C8 120.2(7) . . ? C7 N1 Fe1 123.8(6) . . ? C8 N1 Fe1 116.0(5) . . ? C16 N2 C13 119.6(8) . . ? C16 N2 Fe1 125.7(6) . . ? C13 N2 Fe1 114.7(6) . . ? C35 N20 C32 119.7(9) . . ? C35 N20 Fe1 126.7(7) . . ? C32 N20 Fe1 113.3(6) . . ? C26 N21 C27 120.0(8) . . ? C26 N21 Fe1 125.1(7) . . ? C27 N21 Fe1 114.8(5) . . ? O1 C1 C2 119.6(8) . . ? O1 C1 C6 121.3(8) . . ? C2 C1 C6 119.1(8) . . ? C3 C2 C1 121.8(9) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 C3 C4 119.5(9) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.9(8) . . ? C5 C4 I1 118.8(7) . . ? C3 C4 I1 120.3(7) . . ? C4 C5 C6 120.3(8) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 116.7(8) . . ? C7 C6 C1 124.8(8) . . ? C5 C6 C1 118.5(8) . . ? N1 C7 C6 126.8(8) . . ? N1 C7 H7 116.6 . . ? C6 C7 H7 116.6 . . ? C9 C8 N1 126.4(8) . . ? C9 C8 C13 118.4(8) . . ? N1 C8 C13 115.1(8) . . ? C8 C9 C10 118.7(9) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 123.5(10) . . ? C11 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? C10 C11 C12 119.5(11) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C11 C12 C14 124.5(10) . . ? C11 C12 C13 118.8(9) . . ? C14 C12 C13 116.7(9) . . ? N2 C13 C8 117.3(8) . . ? N2 C13 C12 121.7(8) . . ? C8 C13 C12 121.0(8) . . ? C15 C14 C12 120.0(10) . . ? C15 C14 H14 120.0 . . ? C12 C14 H14 120.0 . . ? C14 C15 C16 121.3(10) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? N2 C16 C15 120.7(9) . . ? N2 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? O20 C20 C21 118.8(9) . . ? O20 C20 C25 123.3(9) . . ? C21 C20 C25 117.9(9) . . ? C22 C21 C20 121.2(10) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 119.4(11) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C24 C23 C22 118.8(9) . . ? C24 C23 I2 123.8(8) . . ? C22 C23 I2 117.4(9) . . ? C23 C24 C25 123.0(10) . . ? C23 C24 H24 118.5 . . ? C25 C24 H24 118.5 . . ? C24 C25 C20 119.7(10) . . ? C24 C25 C26 117.3(10) . . ? C20 C25 C26 123.0(9) . . ? N21 C26 C25 126.9(9) . . ? N21 C26 H26 116.6 . . ? C25 C26 H26 116.6 . . ? C28 C27 C32 118.3(10) . . ? C28 C27 N21 127.5(8) . . ? C32 C27 N21 114.2(8) . . ? C27 C28 C29 121.4(10) . . ? C27 C28 H28 119.3 . . ? C29 C28 H28 119.3 . . ? C30 C29 C28 122.2(10) . . ? C30 C29 H29 118.9 . . ? C28 C29 H29 118.9 . . ? C29 C30 C31 118.5(11) . . ? C29 C30 H30 120.8 . . ? C31 C30 H30 120.8 . . ? C33 C31 C30 122.7(11) . . ? C33 C31 C32 117.7(9) . . ? C30 C31 C32 119.6(9) . . ? N20 C32 C27 119.7(9) . . ? N20 C32 C31 120.3(8) . . ? C27 C32 C31 120.0(8) . . ? C34 C33 C31 121.0(10) . . ? C34 C33 H33 119.5 . . ? C31 C33 H33 119.5 . . ? C33 C34 C35 118.4(10) . . ? C33 C34 H34 120.8 . . ? C35 C34 H34 120.8 . . ? N20 C35 C34 123.0(9) . . ? N20 C35 H35 118.5 . . ? C34 C35 H35 118.5 . . ? F1 C100 F3 110.8(17) . . ? F1 C100 F2 106.7(16) . . ? F3 C100 F2 107.6(15) . . ? F1 C100 S1 113.9(13) . . ? F3 C100 S1 112.7(13) . . ? F2 C100 S1 104.7(13) . . ? O200 C200 H20A 109.5 . . ? O200 C200 H20B 109.5 . . ? H20A C200 H20B 109.5 . . ? O200 C200 H20C 109.5 . . ? H20A C200 H20C 109.5 . . ? H20B C200 H20C 109.5 . . ? C1 O1 Fe1 133.5(6) . . ? C20 O20 Fe1 132.4(6) . . ? C200 O200 H200 109.5 . . ? O100 S1 O102 115.9(7) . . ? O100 S1 O101 116.1(7) . . ? O102 S1 O101 113.4(7) . . ? O100 S1 C100 102.8(8) . . ? O102 S1 C100 104.8(7) . . ? O101 S1 C100 101.3(9) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 66.54 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.719 _refine_diff_density_min -1.539 _refine_diff_density_rms 0.125 _database_code_depnum_ccdc_archive 'CCDC 929014' ####################################################################### # # 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_wp91-mt2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H24 F3 Fe I2 N4 O6 S' _chemical_formula_weight 983.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.2189(5) _cell_length_b 12.4526(7) _cell_length_c 12.8877(9) _cell_angle_alpha 70.115(5) _cell_angle_beta 87.282(6) _cell_angle_gamma 68.604(5) _cell_volume 1710.35(17) _cell_formula_units_Z 2 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used 3828 _cell_measurement_theta_min 6.6 _cell_measurement_theta_max 71.1 _exptl_crystal_description rod _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.909 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 958 _exptl_absorpt_coefficient_mu 18.879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.36 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 230(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rigaku MM007 rotating anode' _diffrn_radiation_monochromator 'Rigaku VariMax-HF Confocal Optical System' _diffrn_measurement_device_type 'Rigaku Spider' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22723 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 6.61 _diffrn_reflns_theta_max 71.83 _reflns_number_total 6316 _reflns_number_gt 4798 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_data_reduction 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _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^)+(0.0836P)^2^+5.4201P] 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 6316 _refine_ls_number_parameters 462 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.2060 _refine_ls_wR_factor_gt 0.1705 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.168 _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 0.11822(10) 0.21637(12) 0.96139(9) 0.0377(3) Uani 1 1 d . . . I1 I -0.03044(5) 0.35691(7) 1.48993(5) 0.0629(2) Uani 1 1 d . . . I2 I -0.36498(5) 0.26638(7) 0.57939(5) 0.0671(3) Uani 1 1 d . . . N1 N 0.1424(5) 0.3480(7) 0.9945(5) 0.0426(16) Uani 1 1 d . . . N2 N 0.1961(5) 0.2742(7) 0.8251(5) 0.0405(15) Uani 1 1 d . . . N20 N 0.2763(5) 0.0912(6) 1.0343(5) 0.0386(15) Uani 1 1 d . . . N21 N 0.1077(5) 0.0791(7) 0.9251(5) 0.0415(16) Uani 1 1 d . . . C1 C 0.0339(6) 0.2108(8) 1.1742(6) 0.0405(18) Uani 1 1 d . . . C2 C -0.0166(7) 0.1570(9) 1.2702(7) 0.051(2) Uani 1 1 d . . . H2 H -0.0376 0.0905 1.2733 0.061 Uiso 1 1 calc R . . C3 C -0.0358(8) 0.1973(8) 1.3576(7) 0.0461(19) Uani 1 1 d . . . H3 H -0.0683 0.1581 1.4198 0.055 Uiso 1 1 calc R . . C4 C -0.0069(7) 0.2976(9) 1.3547(7) 0.050(2) Uani 1 1 d . . . C5 C 0.0373(7) 0.3551(9) 1.2619(7) 0.048(2) Uani 1 1 d . . . H5 H 0.0534 0.4242 1.2590 0.058 Uiso 1 1 calc R . . C6 C 0.0594(6) 0.3145(7) 1.1707(6) 0.0365(17) Uani 1 1 d . . . C7 C 0.1111(6) 0.3789(7) 1.0808(7) 0.0390(17) Uani 1 1 d . . . H7 H 0.1230 0.4479 1.0848 0.047 Uiso 1 1 calc R . . C8 C 0.2002(6) 0.4158(8) 0.9120(6) 0.0389(18) Uani 1 1 d . . . C9 C 0.2330(7) 0.5079(8) 0.9144(7) 0.048(2) Uani 1 1 d . . . H9 H 0.2168 0.5365 0.9743 0.057 Uiso 1 1 calc R . . C10 C 0.2913(8) 0.5601(9) 0.8268(8) 0.055(2) Uani 1 1 d . . . H10 H 0.3146 0.6233 0.8294 0.066 Uiso 1 1 calc R . . C11 C 0.3149(8) 0.5224(7) 0.7391(7) 0.0450(19) Uani 1 1 d . . . H11 H 0.3532 0.5603 0.6814 0.054 Uiso 1 1 calc R . . C12 C 0.2831(7) 0.4273(9) 0.7328(6) 0.048(2) Uani 1 1 d . . . C13 C 0.2262(6) 0.3714(8) 0.8219(6) 0.0430(19) Uani 1 1 d . . . C14 C 0.3027(7) 0.3804(9) 0.6455(7) 0.051(2) Uani 1 1 d . . . H14 H 0.3386 0.4152 0.5838 0.062 Uiso 1 1 calc R . . C15 C 0.2703(8) 0.2853(10) 0.6488(7) 0.054(2) Uani 1 1 d . . . H15 H 0.2837 0.2552 0.5897 0.065 Uiso 1 1 calc R . . C16 C 0.2168(7) 0.2325(8) 0.7413(6) 0.0433(19) Uani 1 1 d . . . H16 H 0.1955 0.1665 0.7437 0.052 Uiso 1 1 calc R . . C20 C -0.0965(7) 0.3081(8) 0.8230(7) 0.044(2) Uani 1 1 d . . . C21 C -0.1979(7) 0.4113(8) 0.7628(7) 0.049(2) Uani 1 1 d . . . H21 H -0.2122 0.4888 0.7675 0.058 Uiso 1 1 calc R . . C22 C -0.2752(8) 0.3981(9) 0.6979(7) 0.050(2) Uani 1 1 d . . . H22 H -0.3425 0.4663 0.6599 0.060 Uiso 1 1 calc R . . C23 C -0.2540(7) 0.2842(9) 0.6883(7) 0.048(2) Uani 1 1 d . . . C24 C -0.1572(7) 0.1831(8) 0.7458(7) 0.0429(19) Uani 1 1 d . . . H24 H -0.1445 0.1063 0.7401 0.051 Uiso 1 1 calc R . . C25 C -0.0777(7) 0.1938(8) 0.8124(7) 0.0403(18) Uani 1 1 d . . . C26 C 0.0219(6) 0.0833(8) 0.8672(6) 0.0400(18) Uani 1 1 d . . . H26 H 0.0246 0.0096 0.8605 0.048 Uiso 1 1 calc R . . C27 C 0.2066(7) -0.0322(8) 0.9715(6) 0.0425(19) Uani 1 1 d . . . C28 C 0.2219(7) -0.1485(8) 0.9640(7) 0.046(2) Uani 1 1 d . . . H28 H 0.1642 -0.1572 0.9252 0.056 Uiso 1 1 calc R . . C29 C 0.3244(8) -0.2490(9) 1.0156(7) 0.055(2) Uani 1 1 d . . . H29 H 0.3347 -0.3258 1.0111 0.066 Uiso 1 1 calc R . . C30 C 0.4110(8) -0.2399(9) 1.0728(7) 0.050(2) Uani 1 1 d . . . H30 H 0.4787 -0.3099 1.1067 0.060 Uiso 1 1 calc R . . C31 C 0.3983(7) -0.1262(8) 1.0805(6) 0.0431(19) Uani 1 1 d . . . C32 C 0.2947(7) -0.0228(8) 1.0288(6) 0.0387(17) Uani 1 1 d . . . C33 C 0.4815(7) -0.1086(9) 1.1383(7) 0.048(2) Uani 1 1 d . . . H33 H 0.5508 -0.1751 1.1745 0.057 Uiso 1 1 calc R . . C34 C 0.4614(7) 0.0043(9) 1.1416(7) 0.052(2) Uani 1 1 d . . . H34 H 0.5172 0.0162 1.1798 0.062 Uiso 1 1 calc R . . C35 C 0.3560(7) 0.1056(9) 1.0875(7) 0.050(2) Uani 1 1 d . . . H35 H 0.3435 0.1837 1.0900 0.060 Uiso 1 1 calc R . . C100 C 0.3942(10) 0.1983(11) 0.3660(9) 0.066(3) Uani 1 1 d . . . C200 C 0.7859(15) -0.0072(15) 0.4101(12) 0.116(5) Uani 1 1 d . . . H20A H 0.8057 -0.0944 0.4500 0.173 Uiso 1 1 calc R . . H20B H 0.7085 0.0387 0.4272 0.173 Uiso 1 1 calc R . . H20C H 0.8440 0.0188 0.4323 0.173 Uiso 1 1 calc R . . O1 O 0.0514(5) 0.1638(6) 1.0955(4) 0.0464(14) Uani 1 1 d . . . O20 O -0.0275(5) 0.3294(5) 0.8844(4) 0.0462(14) Uani 1 1 d . . . O100 O 0.4895(7) 0.3550(8) 0.2945(8) 0.092(3) Uani 1 1 d . . . O101 O 0.5550(6) 0.1801(8) 0.2326(7) 0.087(2) Uani 1 1 d . . . O102 O 0.3626(6) 0.3383(7) 0.1660(5) 0.0674(18) Uani 1 1 d . . . O200 O 0.7852(7) 0.0136(9) 0.3024(7) 0.086(2) Uani 1 1 d . . . H200 H 0.7160 0.0452 0.2745 0.129 Uiso 1 1 calc R . . F1 F 0.3619(8) 0.1157(8) 0.3446(6) 0.114(3) Uani 1 1 d . . . F2 F 0.2965(6) 0.2750(8) 0.3912(5) 0.098(2) Uani 1 1 d . . . F3 F 0.4663(7) 0.1365(8) 0.4588(6) 0.111(3) Uani 1 1 d . . . S1 S 0.4578(2) 0.2766(3) 0.2519(2) 0.0607(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0383(6) 0.0490(8) 0.0309(6) -0.0177(5) 0.0029(5) -0.0186(6) I1 0.0636(4) 0.0871(5) 0.0478(4) -0.0383(3) 0.0089(3) -0.0258(4) I2 0.0536(4) 0.0883(5) 0.0620(4) -0.0239(4) -0.0102(3) -0.0296(4) N1 0.033(3) 0.064(5) 0.029(3) -0.014(3) -0.001(2) -0.018(3) N2 0.037(3) 0.059(4) 0.031(3) -0.020(3) 0.003(2) -0.021(3) N20 0.036(3) 0.049(4) 0.028(3) -0.010(3) 0.004(2) -0.017(3) N21 0.033(3) 0.061(4) 0.032(3) -0.021(3) 0.006(2) -0.015(3) C1 0.033(4) 0.051(5) 0.039(4) -0.015(4) 0.005(3) -0.018(4) C2 0.049(5) 0.057(6) 0.045(5) -0.019(4) 0.008(4) -0.017(4) C3 0.059(5) 0.045(5) 0.043(4) -0.022(4) 0.012(4) -0.024(4) C4 0.039(4) 0.075(6) 0.042(4) -0.031(4) 0.011(3) -0.019(4) C5 0.041(4) 0.065(6) 0.044(4) -0.022(4) 0.009(3) -0.024(4) C6 0.033(3) 0.040(4) 0.047(4) -0.026(4) 0.005(3) -0.015(3) C7 0.040(4) 0.030(4) 0.049(4) -0.013(4) -0.003(3) -0.015(3) C8 0.040(4) 0.045(5) 0.034(4) -0.007(3) 0.000(3) -0.023(4) C9 0.050(5) 0.051(5) 0.044(4) -0.016(4) 0.007(4) -0.023(4) C10 0.062(5) 0.056(6) 0.056(5) -0.016(5) -0.002(4) -0.034(5) C11 0.061(5) 0.035(4) 0.045(4) -0.013(4) 0.005(4) -0.025(4) C12 0.040(4) 0.060(6) 0.034(4) -0.006(4) -0.002(3) -0.015(4) C13 0.033(4) 0.053(5) 0.040(4) -0.010(4) -0.005(3) -0.017(4) C14 0.048(5) 0.067(6) 0.033(4) -0.011(4) 0.004(3) -0.022(5) C15 0.054(5) 0.083(7) 0.035(4) -0.029(5) 0.005(4) -0.028(5) C16 0.050(4) 0.056(5) 0.038(4) -0.029(4) 0.006(3) -0.024(4) C20 0.036(4) 0.054(5) 0.041(4) -0.013(4) 0.012(3) -0.019(4) C21 0.049(5) 0.045(5) 0.051(5) -0.019(4) 0.004(4) -0.016(4) C22 0.046(4) 0.055(6) 0.050(5) -0.016(4) 0.001(4) -0.020(4) C23 0.042(4) 0.071(6) 0.040(4) -0.017(4) 0.002(3) -0.032(4) C24 0.042(4) 0.049(5) 0.045(4) -0.022(4) 0.005(3) -0.019(4) C25 0.040(4) 0.041(5) 0.044(4) -0.019(4) 0.004(3) -0.017(4) C26 0.041(4) 0.057(5) 0.040(4) -0.032(4) 0.009(3) -0.024(4) C27 0.040(4) 0.051(5) 0.035(4) -0.013(4) 0.010(3) -0.019(4) C28 0.046(4) 0.045(5) 0.046(5) -0.015(4) 0.002(4) -0.016(4) C29 0.064(5) 0.053(6) 0.049(5) -0.017(4) 0.004(4) -0.024(5) C30 0.053(5) 0.048(5) 0.051(5) -0.020(4) 0.003(4) -0.017(4) C31 0.041(4) 0.050(5) 0.035(4) -0.017(4) 0.001(3) -0.012(4) C32 0.041(4) 0.045(5) 0.031(4) -0.013(4) 0.006(3) -0.019(4) C33 0.046(4) 0.050(5) 0.042(4) -0.013(4) -0.003(3) -0.014(4) C34 0.047(4) 0.061(6) 0.043(4) -0.017(4) -0.012(4) -0.015(4) C35 0.041(4) 0.073(6) 0.038(4) -0.022(4) 0.001(3) -0.020(4) C100 0.079(7) 0.069(7) 0.057(6) -0.038(5) 0.001(5) -0.022(6) C200 0.125(12) 0.126(14) 0.083(10) -0.019(9) 0.016(9) -0.049(11) O1 0.050(3) 0.065(4) 0.037(3) -0.024(3) 0.009(2) -0.029(3) O20 0.041(3) 0.054(4) 0.043(3) -0.021(3) -0.001(2) -0.013(3) O100 0.084(5) 0.092(6) 0.133(7) -0.060(6) 0.008(5) -0.049(5) O101 0.055(4) 0.111(7) 0.101(6) -0.059(5) 0.017(4) -0.015(4) O102 0.073(4) 0.069(5) 0.055(4) -0.020(3) -0.002(3) -0.022(4) O200 0.068(5) 0.099(7) 0.096(6) -0.047(5) 0.019(4) -0.026(5) F1 0.157(7) 0.128(7) 0.096(5) -0.043(5) 0.045(5) -0.096(6) F2 0.078(4) 0.141(7) 0.066(4) -0.044(4) 0.025(3) -0.025(4) F3 0.117(6) 0.124(7) 0.062(4) -0.009(4) -0.019(4) -0.031(5) S1 0.0494(12) 0.0799(18) 0.0649(14) -0.0356(13) 0.0099(10) -0.0283(12) _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 O20 1.878(5) . ? Fe1 O1 1.890(5) . ? Fe1 N1 1.948(8) . ? Fe1 N21 1.966(7) . ? Fe1 N2 1.997(6) . ? Fe1 N20 2.005(6) . ? I1 C4 2.084(8) . ? I2 C23 2.114(8) . ? N1 C7 1.295(10) . ? N1 C8 1.448(9) . ? N2 C16 1.327(10) . ? N2 C13 1.375(11) . ? N20 C35 1.314(10) . ? N20 C32 1.380(10) . ? N21 C26 1.291(9) . ? N21 C27 1.422(10) . ? C1 O1 1.306(10) . ? C1 C6 1.422(11) . ? C1 C2 1.423(11) . ? C2 C3 1.360(12) . ? C2 H2 0.9400 . ? C3 C4 1.405(12) . ? C3 H3 0.9400 . ? C4 C5 1.368(11) . ? C5 C6 1.408(11) . ? C5 H5 0.9400 . ? C6 C7 1.432(11) . ? C7 H7 0.9400 . ? C8 C9 1.355(11) . ? C8 C13 1.425(11) . ? C9 C10 1.403(12) . ? C9 H9 0.9400 . ? C10 C11 1.346(12) . ? C10 H10 0.9400 . ? C11 C12 1.401(12) . ? C11 H11 0.9400 . ? C12 C14 1.409(12) . ? C12 C13 1.421(11) . ? C14 C15 1.366(13) . ? C14 H14 0.9400 . ? C15 C16 1.410(12) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? C20 O20 1.333(10) . ? C20 C25 1.411(12) . ? C20 C21 1.429(11) . ? C21 C22 1.378(12) . ? C21 H21 0.9400 . ? C22 C23 1.394(13) . ? C22 H22 0.9400 . ? C23 C24 1.376(12) . ? C24 C25 1.396(11) . ? C24 H24 0.9400 . ? C25 C26 1.439(11) . ? C26 H26 0.9400 . ? C27 C32 1.395(11) . ? C27 C28 1.427(12) . ? C28 C29 1.395(12) . ? C28 H28 0.9400 . ? C29 C30 1.376(13) . ? C29 H29 0.9400 . ? C30 C31 1.405(12) . ? C30 H30 0.9400 . ? C31 C33 1.408(11) . ? C31 C32 1.419(11) . ? C33 C34 1.351(12) . ? C33 H33 0.9400 . ? C34 C35 1.427(12) . ? C34 H34 0.9400 . ? C35 H35 0.9400 . ? C100 F3 1.333(12) . ? C100 F2 1.337(12) . ? C100 F1 1.338(12) . ? C100 S1 1.785(12) . ? C200 O200 1.323(15) . ? C200 H20A 0.9700 . ? C200 H20B 0.9700 . ? C200 H20C 0.9700 . ? O100 S1 1.437(8) . ? O101 S1 1.432(8) . ? O102 S1 1.435(7) . ? O200 H200 0.8300 . ? 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 O20 Fe1 O1 93.8(2) . . ? O20 Fe1 N1 89.3(3) . . ? O1 Fe1 N1 94.0(3) . . ? O20 Fe1 N21 94.2(3) . . ? O1 Fe1 N21 89.1(3) . . ? N1 Fe1 N21 175.2(3) . . ? O20 Fe1 N2 88.4(2) . . ? O1 Fe1 N2 176.2(3) . . ? N1 Fe1 N2 82.9(3) . . ? N21 Fe1 N2 93.9(3) . . ? O20 Fe1 N20 175.8(3) . . ? O1 Fe1 N20 89.0(2) . . ? N1 Fe1 N20 93.6(3) . . ? N21 Fe1 N20 82.7(3) . . ? N2 Fe1 N20 89.0(2) . . ? C7 N1 C8 119.0(7) . . ? C7 N1 Fe1 126.2(5) . . ? C8 N1 Fe1 114.8(5) . . ? C16 N2 C13 119.7(7) . . ? C16 N2 Fe1 127.8(6) . . ? C13 N2 Fe1 112.4(5) . . ? C35 N20 C32 119.9(7) . . ? C35 N20 Fe1 127.9(6) . . ? C32 N20 Fe1 112.1(5) . . ? C26 N21 C27 120.9(7) . . ? C26 N21 Fe1 126.2(6) . . ? C27 N21 Fe1 113.0(5) . . ? O1 C1 C6 124.8(7) . . ? O1 C1 C2 118.5(8) . . ? C6 C1 C2 116.6(8) . . ? C3 C2 C1 123.0(9) . . ? C3 C2 H2 118.5 . . ? C1 C2 H2 118.5 . . ? C2 C3 C4 119.8(8) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 118.9(8) . . ? C5 C4 I1 120.7(7) . . ? C3 C4 I1 120.4(6) . . ? C4 C5 C6 122.5(9) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C5 C6 C1 119.0(7) . . ? C5 C6 C7 117.1(7) . . ? C1 C6 C7 123.8(7) . . ? N1 C7 C6 124.1(7) . . ? N1 C7 H7 118.0 . . ? C6 C7 H7 118.0 . . ? C9 C8 C13 120.2(7) . . ? C9 C8 N1 128.2(8) . . ? C13 C8 N1 111.6(7) . . ? C8 C9 C10 119.5(8) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 121.9(8) . . ? C11 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C10 C11 C12 120.8(8) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C14 126.0(8) . . ? C11 C12 C13 118.1(8) . . ? C14 C12 C13 115.9(9) . . ? N2 C13 C12 122.3(8) . . ? N2 C13 C8 118.3(7) . . ? C12 C13 C8 119.4(8) . . ? C15 C14 C12 121.2(8) . . ? C15 C14 H14 119.4 . . ? C12 C14 H14 119.4 . . ? C14 C15 C16 119.6(8) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? N2 C16 C15 121.2(8) . . ? N2 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? O20 C20 C25 125.9(7) . . ? O20 C20 C21 116.3(8) . . ? C25 C20 C21 117.8(8) . . ? C22 C21 C20 120.6(8) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 120.4(8) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 120.3(8) . . ? C24 C23 I2 119.2(7) . . ? C22 C23 I2 120.5(6) . . ? C23 C24 C25 120.6(8) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C24 C25 C20 120.4(7) . . ? C24 C25 C26 116.3(7) . . ? C20 C25 C26 123.3(7) . . ? N21 C26 C25 124.2(8) . . ? N21 C26 H26 117.9 . . ? C25 C26 H26 117.9 . . ? C32 C27 N21 114.9(8) . . ? C32 C27 C28 119.1(7) . . ? N21 C27 C28 126.1(7) . . ? C29 C28 C27 118.4(8) . . ? C29 C28 H28 120.8 . . ? C27 C28 H28 120.8 . . ? C30 C29 C28 122.5(9) . . ? C30 C29 H29 118.7 . . ? C28 C29 H29 118.7 . . ? C29 C30 C31 120.0(8) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? C30 C31 C33 124.0(8) . . ? C30 C31 C32 118.4(8) . . ? C33 C31 C32 117.6(8) . . ? N20 C32 C27 117.2(7) . . ? N20 C32 C31 121.3(7) . . ? C27 C32 C31 121.5(8) . . ? C34 C33 C31 119.8(8) . . ? C34 C33 H33 120.1 . . ? C31 C33 H33 120.1 . . ? C33 C34 C35 120.4(8) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? N20 C35 C34 121.0(9) . . ? N20 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? F3 C100 F2 106.5(9) . . ? F3 C100 F1 105.8(10) . . ? F2 C100 F1 105.7(10) . . ? F3 C100 S1 113.9(8) . . ? F2 C100 S1 112.3(8) . . ? F1 C100 S1 112.0(7) . . ? O200 C200 H20A 109.5 . . ? O200 C200 H20B 109.5 . . ? H20A C200 H20B 109.5 . . ? O200 C200 H20C 109.5 . . ? H20A C200 H20C 109.5 . . ? H20B C200 H20C 109.5 . . ? C1 O1 Fe1 126.9(5) . . ? C20 O20 Fe1 125.9(5) . . ? C200 O200 H200 109.5 . . ? O101 S1 O102 114.4(5) . . ? O101 S1 O100 115.2(5) . . ? O102 S1 O100 115.5(5) . . ? O101 S1 C100 104.1(5) . . ? O102 S1 C100 102.8(5) . . ? O100 S1 C100 102.3(5) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 71.83 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 1.397 _refine_diff_density_min -1.868 _refine_diff_density_rms 0.159 _database_code_depnum_ccdc_archive 'CCDC 940198'