# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Ashwini Nangia' _publ_contact_author_email 'ASHWINI NANGIA@REDIFFMAIL.COM' _publ_section_title ; Isostructural polymorphs of triiodophloroglucinol and triiodoresorcinol ; loop_ _publ_author_name 'Ashwini Nangia' 'Naba K. Nath' 'Binoy K Saha' # Attachment 'B804905J_tig-m.cif' data_an719_m-tig-m _database_code_depnum_ccdc_archive 'CCDC 687008' _audit_creation_method SHELXL-97 _chemical_name_systematic ; triiodophloroglucinol ; _chemical_name_common triiodophloroglucinol _chemical_melting_point ? _chemical_formula_moiety 'C6 H3 I3 O3' _chemical_formula_sum 'C6 H3 I3 O3' _chemical_formula_weight 503.78 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.582(4) _cell_length_b 4.5004(13) _cell_length_c 15.507(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.569(4) _cell_angle_gamma 90.00 _cell_volume 970.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3917 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 26.06 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 9.631 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2490 _exptl_absorpt_correction_T_max 0.680 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8806 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 26.10 _reflns_number_total 1859 _reflns_number_gt 1719 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SAINT' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+16.0172P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1859 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_restrained_S_all 1.187 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I2 I 0.59019(5) 1.28532(16) 0.10393(4) 0.0208(2) Uani 1 1 d . . . I1 I 0.35515(5) 0.50799(15) 0.27120(5) 0.0196(2) Uani 1 1 d . . . I3 I 0.71423(5) 1.0982(2) 0.50687(5) 0.0271(2) Uani 1 1 d . . . O1 O 0.5260(5) 0.6991(18) 0.4434(5) 0.0236(17) Uani 1 1 d . . . O3 O 0.7097(5) 1.3296(19) 0.3102(5) 0.0257(18) Uani 1 1 d . . . C4 C 0.5685(7) 1.091(2) 0.2178(6) 0.014(2) Uani 1 1 d . . . C6 C 0.6205(7) 1.012(2) 0.3792(6) 0.016(2) Uani 1 1 d . . . C5 C 0.6334(7) 1.145(2) 0.3028(7) 0.016(2) Uani 1 1 d . . . C2 C 0.4770(7) 0.778(2) 0.2869(7) 0.016(2) Uani 1 1 d . . . C1 C 0.5401(7) 0.828(2) 0.3695(7) 0.018(2) Uani 1 1 d . . . O2 O 0.4234(5) 0.8667(17) 0.1269(5) 0.0203(16) Uani 1 1 d . . . C3 C 0.4891(7) 0.909(2) 0.2087(7) 0.016(2) 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 I2 0.0183(4) 0.0263(4) 0.0209(4) 0.0078(3) 0.0108(3) 0.0039(3) I1 0.0107(3) 0.0214(4) 0.0311(4) 0.0002(3) 0.0129(3) -0.0005(3) I3 0.0109(3) 0.0522(5) 0.0164(4) -0.0047(3) 0.0014(3) 0.0036(3) O1 0.018(4) 0.034(4) 0.026(4) 0.012(3) 0.017(3) 0.001(3) O3 0.013(4) 0.038(5) 0.026(4) 0.003(3) 0.005(3) -0.005(3) C4 0.016(5) 0.012(5) 0.015(5) 0.002(4) 0.006(4) 0.006(4) C6 0.006(4) 0.030(6) 0.010(4) -0.001(4) 0.000(4) 0.005(4) C5 0.008(5) 0.022(5) 0.021(5) 0.003(4) 0.006(4) -0.002(4) C2 0.010(5) 0.012(5) 0.027(5) -0.004(4) 0.008(4) 0.000(4) C1 0.013(5) 0.027(6) 0.020(5) 0.008(4) 0.013(4) 0.010(4) O2 0.014(4) 0.030(4) 0.015(4) 0.000(3) 0.002(3) -0.003(3) C3 0.005(4) 0.025(5) 0.020(5) 0.004(4) 0.007(4) 0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I2 C4 2.078(10) . ? I1 C2 2.105(10) . ? I3 C6 2.075(10) . ? O1 C1 1.355(12) . ? O3 C5 1.365(12) . ? C4 C3 1.390(14) . ? C4 C5 1.393(14) . ? C6 C5 1.389(14) . ? C6 C1 1.405(15) . ? C2 C1 1.352(15) . ? C2 C3 1.406(14) . ? O2 C3 1.353(12) . ? 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 C3 C4 C5 120.4(9) . . ? C3 C4 I2 119.9(7) . . ? C5 C4 I2 119.7(7) . . ? C5 C6 C1 119.1(9) . . ? C5 C6 I3 120.9(8) . . ? C1 C6 I3 120.0(7) . . ? O3 C5 C6 120.5(9) . . ? O3 C5 C4 119.3(9) . . ? C6 C5 C4 120.2(9) . . ? C1 C2 C3 121.3(9) . . ? C1 C2 I1 121.0(8) . . ? C3 C2 I1 117.6(7) . . ? C2 C1 O1 119.7(10) . . ? C2 C1 C6 120.5(9) . . ? O1 C1 C6 119.8(9) . . ? O2 C3 C4 120.6(9) . . ? O2 C3 C2 120.8(9) . . ? C4 C3 C2 118.5(9) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 26.10 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.919 _refine_diff_density_min -1.633 _refine_diff_density_rms 0.305 # Attachment 'B804905J_tig-o.cif' data_an550_m_tig-o _database_code_depnum_ccdc_archive 'CCDC 687009' _audit_creation_method SHELXL-97 _chemical_name_systematic ; triiododphlorogluicinol ; _chemical_name_common triiododphlorogluicinol _chemical_melting_point ? _chemical_formula_moiety 'C6 H3 I3 O3' _chemical_formula_sum 'C6 H3 I3 O3' _chemical_formula_weight 503.78 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.6376(4) _cell_length_b 13.5291(11) _cell_length_c 15.3446(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 962.76(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5463 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 26.00 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 9.705 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2240 _exptl_absorpt_correction_T_max 0.418 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction-V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5921 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1805 _reflns_number_gt 1800 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+1.6706P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.94(6) _refine_ls_number_reflns 1805 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0242 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0603 _refine_ls_wR_factor_gt 0.0602 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I2 I 1.00004(8) -0.16223(3) 0.07919(2) 0.01483(12) Uani 1 1 d . . . I3 I 0.36762(8) 0.17379(3) 0.25608(2) 0.01461(12) Uani 1 1 d . . . I1 I 0.22600(8) 0.11107(3) -0.12764(2) 0.01425(12) Uani 1 1 d . . . O2 O 0.6729(10) -0.0697(3) -0.0771(3) 0.0175(9) Uani 1 1 d . . . O3 O 0.7802(10) -0.0090(3) 0.2267(3) 0.0166(9) Uani 1 1 d . . . C1 C 0.3495(13) 0.1200(5) 0.0644(4) 0.0150(12) Uani 1 1 d . . . C6 C 0.4742(13) 0.0947(5) 0.1441(4) 0.0143(12) Uani 1 1 d . . . C4 C 0.7306(15) -0.0378(4) 0.0724(4) 0.0137(12) Uani 1 1 d . . . C5 C 0.6650(13) 0.0147(5) 0.1474(4) 0.0130(12) Uani 1 1 d . . . C3 C 0.6088(13) -0.0131(5) -0.0076(4) 0.0134(12) Uani 1 1 d . . . O1 O 0.1550(11) 0.1938(4) 0.0564(3) 0.0185(10) Uani 1 1 d . . . C2 C 0.4190(12) 0.0675(5) -0.0104(4) 0.0121(12) 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 I2 0.01437(18) 0.0118(2) 0.0183(2) 0.00150(15) 0.00164(15) 0.00206(18) I3 0.0195(2) 0.0127(2) 0.01167(19) -0.00072(15) 0.00254(15) -0.00011(16) I1 0.01571(19) 0.0150(2) 0.0120(2) 0.00012(14) -0.00234(14) 0.00020(16) O2 0.021(2) 0.017(2) 0.0144(19) -0.0033(18) 0.0029(19) 0.005(2) O3 0.021(2) 0.019(2) 0.0098(19) -0.0014(16) -0.0028(18) 0.006(2) C1 0.015(3) 0.011(3) 0.018(3) 0.002(2) -0.002(3) 0.000(3) C6 0.013(3) 0.016(3) 0.013(3) -0.004(2) 0.000(2) -0.003(3) C4 0.013(3) 0.010(3) 0.018(3) 0.001(2) 0.003(3) -0.001(3) C5 0.013(3) 0.014(3) 0.012(3) 0.001(2) -0.002(2) -0.002(2) C3 0.014(3) 0.016(3) 0.011(3) -0.001(2) 0.002(2) -0.009(3) O1 0.021(2) 0.019(3) 0.016(2) 0.0001(18) -0.0031(18) 0.0060(19) C2 0.016(3) 0.011(3) 0.009(3) 0.002(2) -0.001(2) 0.000(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 I2 C4 2.099(6) . ? I3 C6 2.084(6) . ? I1 C2 2.094(6) . ? O2 C3 1.345(8) . ? O3 C5 1.367(7) . ? C1 O1 1.352(8) . ? C1 C2 1.387(9) . ? C1 C6 1.396(8) . ? C6 C5 1.399(9) . ? C4 C5 1.385(8) . ? C4 C3 1.392(9) . ? C3 C2 1.402(9) . ? 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 C1 C2 117.3(5) . . ? O1 C1 C6 122.5(6) . . ? C2 C1 C6 120.2(6) . . ? C1 C6 C5 118.9(6) . . ? C1 C6 I3 119.9(5) . . ? C5 C6 I3 121.2(5) . . ? C5 C4 C3 121.4(6) . . ? C5 C4 I2 120.0(4) . . ? C3 C4 I2 118.5(5) . . ? O3 C5 C4 122.2(5) . . ? O3 C5 C6 117.4(5) . . ? C4 C5 C6 120.3(6) . . ? O2 C3 C4 118.2(6) . . ? O2 C3 C2 123.9(5) . . ? C4 C3 C2 117.9(5) . . ? C1 C2 C3 121.3(5) . . ? C1 C2 I1 117.8(4) . . ? C3 C2 I1 120.9(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.925 _refine_diff_density_min -1.349 _refine_diff_density_rms 0.236 # Attachment 'B804905J_tip.cif' data_an567_m_tip _database_code_depnum_ccdc_archive 'CCDC 687010' _audit_creation_method SHELXL-97 _chemical_name_systematic ; triiodophenol ; _chemical_name_common triiodophenol _chemical_melting_point ? _chemical_formula_moiety 'C6 H3 I3 O' _chemical_formula_sum 'C6 H3 I3 O' _chemical_formula_weight 471.78 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' 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' _cell_length_a 4.3695(5) _cell_length_b 14.6940(15) _cell_length_c 14.1839(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 910.68(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4674 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 26.01 _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 10.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2225 _exptl_absorpt_correction_T_max 0.541 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4958 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 26.01 _reflns_number_total 1797 _reflns_number_gt 1788 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0266P)^2^+7.3396P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.17(10) _refine_ls_number_reflns 1797 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0701 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _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 I2 I 0.99585(12) -0.15366(4) 0.06286(4) 0.02342(14) Uani 1 1 d . . . I3 I 0.37865(12) 0.15431(4) 0.27120(4) 0.02702(15) Uani 1 1 d . . . I1 I 0.28318(13) 0.12772(4) -0.15112(4) 0.02923(16) Uani 1 1 d . . . C4 C 0.7378(18) -0.0317(5) 0.0631(6) 0.0214(16) Uani 1 1 d . . . C6 C 0.4901(19) 0.0880(5) 0.1455(6) 0.0197(15) Uani 1 1 d . . . O1 O 0.193(2) 0.1940(5) 0.0564(6) 0.052(2) Uani 1 1 d . . . C1 C 0.3735(19) 0.1218(6) 0.0610(6) 0.0229(17) Uani 1 1 d . . . C2 C 0.4495(19) 0.0771(6) -0.0236(6) 0.0208(17) Uani 1 1 d . . . C5 C 0.6765(19) 0.0110(5) 0.1469(6) 0.0234(18) Uani 1 1 d . . . H5 H 0.7572 -0.0108 0.2032 0.028 Uiso 1 1 calc R . . C3 C 0.631(2) 0.0005(5) -0.0231(6) 0.0202(17) Uani 1 1 d . . . H3 H 0.6816 -0.0289 -0.0790 0.024 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 I2 0.0193(2) 0.0203(2) 0.0306(3) 0.0023(2) 0.0006(2) -0.0003(2) I3 0.0253(3) 0.0296(3) 0.0261(3) -0.0008(3) 0.0054(2) -0.0002(2) I1 0.0267(3) 0.0325(3) 0.0285(3) 0.0089(2) -0.0068(2) -0.0040(2) C4 0.013(4) 0.016(3) 0.036(4) 0.001(3) -0.001(4) -0.005(3) C6 0.014(3) 0.019(3) 0.026(4) -0.006(3) 0.003(3) 0.004(3) O1 0.056(5) 0.047(4) 0.054(5) 0.000(4) -0.009(4) 0.014(4) C1 0.016(3) 0.020(4) 0.032(5) 0.001(4) 0.004(4) 0.002(3) C2 0.023(5) 0.020(4) 0.019(4) 0.006(3) -0.003(3) -0.005(3) C5 0.021(4) 0.025(4) 0.024(4) 0.008(3) -0.005(4) -0.012(3) C3 0.019(4) 0.020(4) 0.022(4) -0.003(3) 0.002(4) -0.002(3) _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 I2 C4 2.117(8) . ? I3 C6 2.090(8) . ? I1 C2 2.086(8) . ? C4 C5 1.371(12) . ? C4 C3 1.391(11) . ? C6 C1 1.393(12) . ? C6 C5 1.394(11) . ? O1 C1 1.324(11) . ? C1 C2 1.408(12) . ? C2 C3 1.377(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C4 C3 122.7(7) . . ? C5 C4 I2 119.5(6) . . ? C3 C4 I2 117.7(6) . . ? C1 C6 C5 121.0(8) . . ? C1 C6 I3 118.9(6) . . ? C5 C6 I3 120.2(6) . . ? O1 C1 C6 123.0(8) . . ? O1 C1 C2 118.2(8) . . ? C6 C1 C2 118.8(7) . . ? C3 C2 C1 120.8(7) . . ? C3 C2 I1 119.8(6) . . ? C1 C2 I1 119.4(6) . . ? C4 C5 C6 118.3(8) . . ? C2 C3 C4 118.4(7) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.301 _refine_diff_density_min -1.328 _refine_diff_density_rms 0.191 # Attachment 'tip_tir.cif' data_an570_m_tip+tir-o _database_code_depnum_ccdc_archive 'CCDC 687011' _audit_creation_method SHELXL-97 _chemical_name_systematic ; triiodophenol, triiodoresorcinol ; _chemical_name_common 'triiodophenol, triiodoresorcinol' _chemical_melting_point ? _chemical_formula_moiety 'C6 H3 I3 O, C6 H3 I3 O2' _chemical_formula_sum 'C6 H3 I3 O1.50' _chemical_formula_weight 479.78 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.4419(3) _cell_length_b 14.3683(9) _cell_length_c 14.5730(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 930.09(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8415 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 28.23 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 834 _exptl_absorpt_coefficient_mu 10.024 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1571 _exptl_absorpt_correction_T_max 0.3792 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9609 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.01 _reflns_number_total 1846 _reflns_number_gt 1834 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0220P)^2^+2.6846P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(7) _refine_ls_number_reflns 1846 _refine_ls_number_parameters 112 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0217 _refine_ls_R_factor_gt 0.0215 _refine_ls_wR_factor_ref 0.0536 _refine_ls_wR_factor_gt 0.0535 _refine_ls_goodness_of_fit_ref 1.197 _refine_ls_restrained_S_all 1.198 _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 I2 I 0.99943(9) -0.15388(3) 0.06868(3) 0.03151(10) Uani 1 1 d . . . I3 I 0.37773(9) 0.16146(3) 0.26841(3) 0.03704(11) Uani 1 1 d . . . I1 I 0.26763(10) 0.12760(3) -0.14024(3) 0.04248(13) Uani 1 1 d . . . C6 C 0.4907(15) 0.0915(4) 0.1465(4) 0.0290(12) Uani 1 1 d . . . C3 C 0.6272(15) -0.0012(4) -0.0164(4) 0.0286(13) Uani 1 1 d . . . C4 C 0.7381(13) -0.0316(4) 0.0678(4) 0.0297(12) Uani 1 1 d . . . C5 C 0.6772(12) 0.0141(4) 0.1491(4) 0.0282(13) Uani 1 1 d . . . C2 C 0.4400(13) 0.0775(4) -0.0163(4) 0.0300(13) Uani 1 1 d . . . C1 C 0.3697(14) 0.1238(4) 0.0639(4) 0.0315(13) Uani 1 1 d . . . O1 O 0.1807(17) 0.1938(5) 0.0578(5) 0.040(2) Uani 0.645(12) 1 d P . . O3 O 0.775(2) -0.0152(7) 0.2235(7) 0.031(3) Uani 0.405(12) 1 d P . . O2 O 0.675(2) -0.0466(7) -0.0858(7) 0.038(3) Uani 0.473(12) 1 d P . . 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 I2 0.02194(17) 0.02587(18) 0.0467(2) 0.00084(17) 0.00194(17) -0.00047(18) I3 0.0316(2) 0.0372(2) 0.0423(2) -0.00202(19) 0.01264(18) -0.00192(18) I1 0.0343(2) 0.0443(2) 0.0488(3) 0.01210(19) -0.0123(2) -0.00625(19) C6 0.021(3) 0.029(3) 0.037(3) -0.003(2) 0.009(3) 0.001(3) C3 0.024(3) 0.024(3) 0.037(3) -0.002(2) 0.001(3) -0.005(2) C4 0.015(2) 0.024(3) 0.050(4) 0.000(3) 0.007(3) -0.004(2) C5 0.018(3) 0.024(3) 0.043(4) 0.004(2) 0.003(2) -0.006(2) C2 0.022(3) 0.030(3) 0.038(3) 0.008(3) 0.002(2) -0.005(2) C1 0.021(3) 0.028(3) 0.045(4) 0.007(3) 0.009(3) -0.003(3) O1 0.042(5) 0.028(4) 0.051(5) -0.003(3) 0.002(4) 0.013(3) O3 0.026(5) 0.035(6) 0.031(6) 0.004(4) 0.001(5) 0.009(5) O2 0.030(6) 0.049(6) 0.035(5) -0.012(4) -0.002(4) -0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I2 C4 2.105(6) . ? I3 C6 2.102(6) . ? I1 C2 2.090(6) . ? C6 C5 1.387(8) . ? C6 C1 1.397(9) . ? C3 O2 1.223(11) . ? C3 C4 1.392(9) . ? C3 C2 1.404(9) . ? C4 C5 1.381(9) . ? C5 O3 1.241(11) . ? C2 C1 1.380(9) . ? C1 O1 1.313(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C6 C1 121.3(6) . . ? C5 C6 I3 120.2(5) . . ? C1 C6 I3 118.5(4) . . ? O2 C3 C4 120.0(7) . . ? O2 C3 C2 122.3(7) . . ? C4 C3 C2 117.5(5) . . ? C5 C4 C3 122.5(5) . . ? C5 C4 I2 120.0(4) . . ? C3 C4 I2 117.5(4) . . ? O3 C5 C4 121.3(7) . . ? O3 C5 C6 120.3(7) . . ? C4 C5 C6 118.4(6) . . ? C1 C2 C3 121.5(6) . . ? C1 C2 I1 118.9(4) . . ? C3 C2 I1 119.6(5) . . ? O1 C1 C2 117.1(6) . . ? O1 C1 C6 124.0(6) . . ? C2 C1 C6 118.8(6) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.699 _refine_diff_density_min -0.844 _refine_diff_density_rms 0.147 # Attachment 'B804905J_tir-m.cif' data_an568_m_tir-m _database_code_depnum_ccdc_archive 'CCDC 687012' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Triiodoresorcinol ; _chemical_name_common Triiodoresorcinol _chemical_melting_point ? _chemical_formula_moiety 'C6 H3 I3 O2' _chemical_formula_sum 'C6 H3 I3 O2' _chemical_formula_weight 486.78 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.8819(10) _cell_length_b 4.3317(3) _cell_length_c 15.5848(11) _cell_angle_alpha 90.00 _cell_angle_beta 108.4950(10) _cell_angle_gamma 90.00 _cell_volume 952.77(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7411 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 26.04 _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 9.793 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1702 _exptl_absorpt_correction_T_max 0.376 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction -V2.10 ' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8909 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 26.07 _reflns_number_total 1878 _reflns_number_gt 1853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0304P)^2^+5.7628P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1878 _refine_ls_number_parameters 112 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0700 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_restrained_S_all 1.187 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I3 I 0.71910(2) 1.08550(9) 0.51225(2) 0.02359(12) Uani 1 1 d . . . I1 I 0.35700(2) 0.52268(9) 0.27034(2) 0.02084(12) Uani 1 1 d . . . I2 I 0.60820(3) 1.26325(9) 0.10965(2) 0.02767(13) Uani 1 1 d . . . O1 O 0.5215(3) 0.7041(11) 0.4426(3) 0.0224(9) Uani 0.88 1 d P . . O2 O 0.4328(3) 0.8600(12) 0.1283(3) 0.0247(10) Uani 0.86 1 d P . . C6 C 0.6235(4) 1.0064(13) 0.3830(4) 0.0175(10) Uani 1 1 d . . . C4 C 0.5789(4) 1.0789(13) 0.2220(4) 0.0198(11) Uani 1 1 d . . . C5 C 0.6412(4) 1.1300(13) 0.3077(4) 0.0191(11) Uani 1 1 d D . . C2 C 0.4805(4) 0.7789(13) 0.2867(4) 0.0180(11) Uani 1 1 d . . . C3 C 0.4973(4) 0.9043(13) 0.2103(4) 0.0198(11) Uani 1 1 d . . . C1 C 0.5429(4) 0.8276(13) 0.3729(4) 0.0170(10) Uani 1 1 d . . . O3 O 0.7105(9) 1.330(3) 0.3095(11) 0.036(4) Uani 0.27 1 d PD . . 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 I3 0.0197(2) 0.0343(2) 0.01456(19) -0.00362(14) 0.00242(14) -0.00091(14) I1 0.01376(18) 0.0257(2) 0.0234(2) -0.00270(14) 0.00643(15) -0.00033(13) I2 0.0386(2) 0.0297(2) 0.0180(2) 0.00219(14) 0.01358(17) -0.00328(16) O1 0.021(2) 0.033(3) 0.015(2) 0.0047(18) 0.0068(17) -0.0009(19) O2 0.020(2) 0.039(3) 0.011(2) -0.002(2) -0.0012(18) 0.000(2) C6 0.016(2) 0.020(3) 0.016(3) -0.001(2) 0.004(2) 0.002(2) C4 0.019(3) 0.022(3) 0.018(3) 0.000(2) 0.004(2) 0.001(2) C5 0.017(2) 0.023(3) 0.018(3) -0.001(2) 0.007(2) 0.001(2) C2 0.013(2) 0.021(3) 0.019(3) -0.001(2) 0.005(2) 0.004(2) C3 0.018(2) 0.026(3) 0.016(3) -0.004(2) 0.005(2) 0.003(2) C1 0.020(2) 0.018(3) 0.016(2) 0.004(2) 0.010(2) 0.005(2) O3 0.030(9) 0.052(11) 0.022(8) 0.002(8) 0.004(7) -0.002(8) _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 I3 C6 2.094(5) . ? I1 C2 2.092(5) . ? I2 C4 2.092(6) . ? O1 C1 1.337(7) . ? O2 C3 1.347(7) . ? C6 C5 1.388(8) . ? C6 C1 1.394(8) . ? C4 C5 1.381(8) . ? C4 C3 1.393(8) . ? C5 O3 1.3397(10) . ? C2 C1 1.387(8) . ? C2 C3 1.401(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C6 C1 120.4(5) . . ? C5 C6 I3 119.8(4) . . ? C1 C6 I3 119.8(4) . . ? C5 C4 C3 120.2(5) . . ? C5 C4 I2 119.6(4) . . ? C3 C4 I2 120.2(4) . . ? O3 C5 C4 113.6(8) . . ? O3 C5 C6 125.6(8) . . ? C4 C5 C6 120.4(5) . . ? C1 C2 C3 121.3(5) . . ? C1 C2 I1 119.4(4) . . ? C3 C2 I1 119.3(4) . . ? O2 C3 C4 122.1(5) . . ? O2 C3 C2 119.0(5) . . ? C4 C3 C2 118.9(5) . . ? O1 C1 C2 117.9(5) . . ? O1 C1 C6 123.3(5) . . ? C2 C1 C6 118.7(5) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.465 _refine_diff_density_min -1.604 _refine_diff_density_rms 0.197 # Attachment 'B804905J_tir-o.cif' data_an526m_tir-o _database_code_depnum_ccdc_archive 'CCDC 687013' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Triiodoresorcinol ; _chemical_name_common Triiodoresorcinol _chemical_melting_point ? _chemical_formula_moiety 'C6 H3 I3 O2' _chemical_formula_sum 'C6 H3 I3 O2' _chemical_formula_weight 486.78 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.4949(7) _cell_length_b 13.958(2) _cell_length_c 15.036(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 943.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3137 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 26.00 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 9.890 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2196 _exptl_absorpt_correction_T_max 0.500 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction -V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5135 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.01 _reflns_number_total 1861 _reflns_number_gt 1800 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+19.3513P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.98(18) _refine_ls_number_reflns 1861 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1357 _refine_ls_wR_factor_gt 0.1346 _refine_ls_goodness_of_fit_ref 1.256 _refine_ls_restrained_S_all 1.256 _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 I2 I 1.0028(3) -0.15858(8) 0.07696(8) 0.0281(3) Uani 1 1 d . . . I3 I 0.3733(3) 0.16927(8) 0.26149(7) 0.0276(3) Uani 1 1 d . . . I1 I 0.2528(3) 0.11997(10) -0.13199(9) 0.0368(3) Uani 1 1 d . . . C4 C 0.736(4) -0.0359(11) 0.0718(11) 0.021(3) Uani 1 1 d . . . C6 C 0.484(4) 0.0951(11) 0.1466(10) 0.021(3) Uani 1 1 d . . . O2 O 0.676(4) -0.0603(12) -0.0768(11) 0.028(4) Uani 0.70 1 d P . . C3 C 0.622(4) -0.0088(12) -0.0097(12) 0.028(4) Uani 1 1 d . . . C1 C 0.364(4) 0.1228(13) 0.0659(11) 0.028(3) Uani 1 1 d . . . C2 C 0.438(3) 0.0731(14) -0.0143(13) 0.031(4) Uani 1 1 d . . . O3 O 0.787(4) -0.0131(15) 0.2260(11) 0.036(4) Uani 0.68 1 d P . . C5 C 0.673(3) 0.0124(13) 0.1491(12) 0.029(4) Uani 1 1 d . . . O1 O 0.177(4) 0.1935(12) 0.0573(12) 0.023(4) Uani 0.62 1 d P . . 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 I2 0.0146(4) 0.0272(6) 0.0426(6) -0.0002(5) 0.0018(5) 0.0011(5) I3 0.0233(5) 0.0308(6) 0.0287(5) -0.0008(5) 0.0090(5) -0.0009(5) I1 0.0282(6) 0.0437(7) 0.0385(7) 0.0076(6) -0.0112(5) -0.0066(6) C4 0.010(6) 0.025(8) 0.028(8) -0.002(7) 0.001(7) 0.001(6) C6 0.018(7) 0.028(8) 0.017(7) -0.002(7) 0.012(7) -0.001(7) O2 0.027(10) 0.037(9) 0.021(8) -0.002(8) 0.002(7) 0.003(8) C3 0.014(7) 0.025(9) 0.046(11) -0.007(8) 0.005(9) -0.011(8) C1 0.021(7) 0.028(8) 0.034(9) 0.001(8) -0.004(8) 0.006(8) C2 0.014(9) 0.037(10) 0.041(11) -0.009(9) 0.004(7) -0.003(7) O3 0.029(10) 0.059(12) 0.019(8) 0.008(9) 0.004(8) 0.008(9) C5 0.008(8) 0.038(10) 0.041(10) -0.005(9) -0.008(7) -0.010(6) O1 0.025(11) 0.016(8) 0.026(9) 0.005(7) 0.009(8) 0.005(7) _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 I2 C4 2.091(16) . ? I3 C6 2.075(15) . ? I1 C2 2.06(2) . ? C4 C5 1.37(2) . ? C4 C3 1.38(2) . ? C6 C1 1.38(2) . ? C6 C5 1.43(2) . ? O2 C3 1.26(2) . ? C3 C2 1.41(3) . ? C1 O1 1.30(2) . ? C1 C2 1.43(2) . ? O3 C5 1.31(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C4 C3 122.6(15) . . ? C5 C4 I2 119.3(12) . . ? C3 C4 I2 118.1(12) . . ? C1 C6 C5 118.7(15) . . ? C1 C6 I3 119.7(12) . . ? C5 C6 I3 121.5(12) . . ? O2 C3 C4 118.8(17) . . ? O2 C3 C2 122.3(19) . . ? C4 C3 C2 118.9(16) . . ? O1 C1 C6 123.4(16) . . ? O1 C1 C2 115.8(16) . . ? C6 C1 C2 120.7(16) . . ? C3 C2 C1 119.3(18) . . ? C3 C2 I1 122.3(14) . . ? C1 C2 I1 118.3(13) . . ? O3 C5 C4 122.1(17) . . ? O3 C5 C6 118.2(18) . . ? C4 C5 C6 119.7(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.997 _refine_diff_density_min -1.822 _refine_diff_density_rms 0.325 # Attachment 'B804905J_tir_tig.cif' data_an622_m-tir+tig-o _database_code_depnum_ccdc_archive 'CCDC 687014' _audit_creation_method SHELXL-97 _chemical_name_systematic ; triiodoresorcinol, triiodophloroglucinol ; _chemical_name_common 'triiodoresorcinol, triiodophloroglucinol' _chemical_melting_point ? _chemical_formula_moiety 'C6 H3 I3 O2, C6 H3 I3 O3' _chemical_formula_sum 'C6 H3 I3 O2.50' _chemical_formula_weight 495.78 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.5607(3) _cell_length_b 13.6484(8) _cell_length_c 15.3485(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 955.39(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8137 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 26.05 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 9.773 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1359 _exptl_absorpt_correction_T_max 0.376 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9686 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 26.06 _reflns_number_total 1889 _reflns_number_gt 1884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+5.8567P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.97(6) _refine_ls_number_reflns 1889 _refine_ls_number_parameters 112 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0226 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0544 _refine_ls_wR_factor_gt 0.0544 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.180 _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 I2 I 1.00011(10) -0.16250(3) 0.07963(3) 0.02094(11) Uani 1 1 d . . . I3 I 0.36858(10) 0.17264(3) 0.25679(3) 0.02039(11) Uani 1 1 d . . . O3 O 0.7758(14) -0.0110(4) 0.2272(3) 0.0234(16) Uani 0.842(14) 1 d P . . I1 I 0.23601(11) 0.11452(3) -0.12764(3) 0.02491(12) Uani 1 1 d . . . O2 O 0.6762(12) -0.0681(4) -0.0767(3) 0.0224(15) Uani 0.924(15) 1 d P . . O1 O 0.1624(15) 0.1939(4) 0.0564(4) 0.0225(19) Uani 0.755(14) 1 d P . . C4 C 0.7330(16) -0.0381(4) 0.0732(4) 0.0178(12) Uani 1 1 d . . . C1 C 0.3551(15) 0.1219(5) 0.0651(4) 0.0199(13) Uani 1 1 d . . . C6 C 0.4795(16) 0.0935(5) 0.1446(4) 0.0178(13) Uani 1 1 d . . . C5 C 0.6669(14) 0.0139(5) 0.1484(4) 0.0175(13) Uani 1 1 d . . . C3 C 0.6098(15) -0.0127(5) -0.0075(4) 0.0175(13) Uani 1 1 d . . . C2 C 0.4260(14) 0.0690(5) -0.0104(4) 0.0196(14) 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 I2 0.01932(19) 0.0170(2) 0.0265(2) 0.00091(17) 0.00249(18) 0.0016(2) I3 0.0250(2) 0.0186(2) 0.01760(19) -0.00066(17) 0.00401(17) 0.00004(17) O3 0.028(3) 0.030(3) 0.012(3) 0.004(2) -0.003(2) 0.000(3) I1 0.0278(2) 0.0283(2) 0.0187(2) 0.00292(17) -0.00430(18) -0.0002(2) O2 0.028(3) 0.022(3) 0.018(2) -0.001(2) 0.004(2) 0.004(2) O1 0.024(4) 0.021(3) 0.022(3) 0.003(2) -0.001(3) 0.007(3) C4 0.015(3) 0.016(3) 0.021(3) 0.001(2) 0.002(3) 0.000(3) C1 0.021(3) 0.022(3) 0.017(3) 0.003(3) 0.004(3) 0.001(3) C6 0.019(3) 0.019(3) 0.015(3) -0.002(2) 0.003(3) -0.008(3) C5 0.016(3) 0.020(3) 0.017(3) 0.006(2) 0.003(2) -0.002(3) C3 0.016(3) 0.021(3) 0.016(3) 0.001(2) 0.001(3) -0.004(3) C2 0.017(4) 0.022(3) 0.020(3) 0.005(3) -0.001(3) -0.005(3) _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 I2 C4 2.092(6) . ? I3 C6 2.095(6) . ? O3 C5 1.350(8) . ? I1 C2 2.092(7) . ? O2 C3 1.339(8) . ? O1 C1 1.325(9) . ? C4 C5 1.388(9) . ? C4 C3 1.403(9) . ? C1 C6 1.400(9) . ? C1 C2 1.403(9) . ? C6 C5 1.384(9) . ? C3 C2 1.396(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C4 C3 121.4(6) . . ? C5 C4 I2 120.1(5) . . ? C3 C4 I2 118.4(5) . . ? O1 C1 C6 124.2(6) . . ? O1 C1 C2 116.8(6) . . ? C6 C1 C2 119.0(6) . . ? C5 C6 C1 120.3(6) . . ? C5 C6 I3 121.3(5) . . ? C1 C6 I3 118.4(5) . . ? O3 C5 C6 117.5(6) . . ? O3 C5 C4 122.4(6) . . ? C6 C5 C4 120.0(6) . . ? O2 C3 C2 124.2(6) . . ? O2 C3 C4 118.1(6) . . ? C2 C3 C4 117.8(6) . . ? C3 C2 C1 121.5(6) . . ? C3 C2 I1 120.9(5) . . ? C1 C2 I1 117.6(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.085 _refine_diff_density_min -0.591 _refine_diff_density_rms 0.143