# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Ali Morsali' _publ_contact_author_email 'morsali a@yahoo.com' _publ_section_title ; Halogen Dipole Moment Effect of Phenolic Ring on Formation of Stair Like Polymers or Polymers with Tetranuclear Cubic Cage Units; New Precursors for Preparation of TlCl and Tl2O3 Nanostructures ; loop_ _publ_author_name A.Morsali K.Akhbari # Attachment '- 1-9.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 643425' #TrackingRef '- 1-9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H3 Cl2 O Tl' _chemical_formula_weight 366.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I41/a _symmetry_space_group_name_Hall '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 17.3760(14) _cell_length_b 17.3760(14) _cell_length_c 10.3040(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3111.0(6) _cell_formula_units_Z 16 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25.01 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.129 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 21.374 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0414 _exptl_absorpt_correction_T_max 0.0686 _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX2 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 7897 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1370 _reflns_number_gt 1198 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _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^)+(0.0109P)^2^+32.1861P] 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 SHELXL _refine_ls_extinction_coef 0.00054(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1370 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0636 _refine_ls_wR_factor_gt 0.0615 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.002 _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 Tl1 Tl 1.028514(19) 0.373142(18) 1.01500(3) 0.04190(17) Uani 1 1 d . . . Cl1 Cl 0.82412(17) 0.41197(16) 1.0147(2) 0.0735(8) Uani 1 1 d . . . Cl2 Cl 0.75547(13) 0.35294(15) 0.5173(2) 0.0556(6) Uani 1 1 d . . . O1 O 0.9162(3) 0.2684(3) 0.9985(5) 0.0402(13) Uani 1 1 d . . . C1 C 0.8800(4) 0.2874(4) 0.8903(8) 0.0330(17) Uani 1 1 d . . . C2 C 0.8340(4) 0.3529(4) 0.8785(7) 0.0339(17) Uani 1 1 d . . . C3 C 0.7955(5) 0.3730(5) 0.7668(8) 0.042(2) Uani 1 1 d . . . H3 H 0.7645 0.4165 0.7648 0.050 Uiso 1 1 calc R . . C4 C 0.8037(4) 0.3279(5) 0.6585(7) 0.0341(18) Uani 1 1 d . . . C5 C 0.8479(5) 0.2631(5) 0.6623(7) 0.0398(19) Uani 1 1 d . . . H5 H 0.8523 0.2320 0.5891 0.048 Uiso 1 1 calc R . . C6 C 0.8862(5) 0.2438(5) 0.7753(7) 0.0382(19) Uani 1 1 d . . . H6 H 0.9173 0.2002 0.7755 0.046 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 Tl1 0.0524(2) 0.0380(2) 0.0353(2) 0.00467(13) 0.00205(14) -0.00137(14) Cl1 0.0954(19) 0.0755(17) 0.0497(15) -0.0286(13) -0.0253(13) 0.0463(15) Cl2 0.0544(13) 0.0777(16) 0.0347(12) 0.0114(11) -0.0153(10) -0.0097(12) O1 0.036(3) 0.049(3) 0.035(3) -0.002(3) -0.011(2) 0.008(2) C1 0.023(4) 0.039(4) 0.038(5) 0.001(3) -0.001(3) 0.001(3) C2 0.038(4) 0.036(4) 0.029(4) -0.009(3) -0.006(3) 0.006(3) C3 0.041(5) 0.045(5) 0.039(5) 0.000(4) -0.011(4) 0.006(4) C4 0.030(4) 0.052(5) 0.020(4) 0.007(3) -0.008(3) -0.013(4) C5 0.057(5) 0.041(5) 0.021(4) -0.002(3) 0.003(4) -0.006(4) C6 0.052(5) 0.035(4) 0.027(4) -0.002(3) 0.002(4) 0.008(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 Tl1 O1 2.537(5) 15_667 ? Tl1 O1 2.646(5) 6_654 ? Tl1 O1 2.674(5) . ? Cl1 C2 1.747(7) . ? Cl2 C4 1.735(7) . ? O1 C1 1.322(9) . ? O1 Tl1 2.537(5) 12_758 ? O1 Tl1 2.646(5) 6_654 ? C1 C2 1.397(10) . ? C1 C6 1.411(11) . ? C2 C3 1.376(10) . ? C3 C4 1.370(11) . ? C3 H3 0.9300 . ? C4 C5 1.364(11) . ? C5 C6 1.382(11) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Tl1 O1 80.60(18) 15_667 6_654 ? O1 Tl1 O1 80.06(18) 15_667 . ? O1 Tl1 O1 68.20(18) 6_654 . ? C1 O1 Tl1 131.7(4) . 12_758 ? C1 O1 Tl1 117.3(4) . 6_654 ? Tl1 O1 Tl1 95.76(17) 12_758 6_654 ? C1 O1 Tl1 103.4(4) . . ? Tl1 O1 Tl1 95.07(17) 12_758 . ? Tl1 O1 Tl1 111.29(18) 6_654 . ? O1 C1 C2 123.3(7) . . ? O1 C1 C6 122.6(7) . . ? C2 C1 C6 114.1(7) . . ? C3 C2 C1 123.8(7) . . ? C3 C2 Cl1 118.4(6) . . ? C1 C2 Cl1 117.7(6) . . ? C4 C3 C2 119.1(7) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C5 C4 C3 120.4(7) . . ? C5 C4 Cl2 120.2(6) . . ? C3 C4 Cl2 119.4(6) . . ? C4 C5 C6 119.7(7) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 122.7(7) . . ? C5 C6 H6 118.6 . . ? C1 C6 H6 118.6 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.902 _refine_diff_density_min -0.798 _refine_diff_density_rms 0.149 data_4 _database_code_depnum_ccdc_archive 'CCDC 758890' #TrackingRef '- 1-9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H2 Cl3 O Tl' _chemical_formula_sum 'C6 H2 Cl3 O Tl' _chemical_formula_weight 400.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.758(15) _cell_length_b 3.8153(18) _cell_length_c 16.345(7) _cell_angle_alpha 90.00 _cell_angle_beta 122.100(1) _cell_angle_gamma 90.00 _cell_volume 1624.9(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1524 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 20.795 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.084 _exptl_absorpt_correction_T_max 0.110 _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _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 'Bruker SMART APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 35656 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 28.98 _reflns_number_total 2153 _reflns_number_gt 2108 _reflns_threshold_expression I>2/s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _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^)+(0.0364P)^2^+2.7776P] 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 2153 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0177 _refine_ls_R_factor_gt 0.0172 _refine_ls_wR_factor_ref 0.0479 _refine_ls_wR_factor_gt 0.0474 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.006 _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 Tl1 Tl 0.512216(4) 0.28709(3) 0.615810(7) 0.02281(6) Uani 1 1 d . . . Cl1 Cl 0.57485(3) 0.3128(2) 0.35364(5) 0.02640(14) Uani 1 1 d . . . Cl2 Cl 0.76635(2) -0.1372(2) 0.62042(5) 0.02553(13) Uani 1 1 d . . . Cl3 Cl 0.61858(3) -0.1382(2) 0.70573(5) 0.02467(13) Uani 1 1 d . . . O1 O 0.55073(8) 0.1654(6) 0.50663(16) 0.0242(4) Uani 1 1 d . . . C1 C 0.59900(10) 0.1017(7) 0.53205(19) 0.0217(5) Uani 1 1 d . . . C2 C 0.61813(11) 0.1556(8) 0.4703(2) 0.0224(5) Uani 1 1 d . . . C3 C 0.66857(10) 0.0878(7) 0.49499(19) 0.0228(5) Uani 1 1 d . . . H3A H 0.6787 0.1316 0.4515 0.027 Uiso 1 1 calc R . . C4 C 0.70279(10) -0.0461(7) 0.5860(2) 0.0227(5) Uani 1 1 d . . . C5 C 0.68731(10) -0.1149(8) 0.65069(19) 0.0226(5) Uani 1 1 d . . . H5A H 0.7103 -0.2079 0.7114 0.027 Uiso 1 1 calc R . . C6 C 0.63662(10) -0.0419(7) 0.62304(18) 0.0216(5) 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 Tl1 0.02287(8) 0.02437(8) 0.02092(8) -0.00118(3) 0.01146(6) 0.00047(3) Cl1 0.0260(3) 0.0330(4) 0.0208(3) 0.0035(2) 0.0129(3) 0.0064(3) Cl2 0.0214(3) 0.0305(3) 0.0254(3) 0.0001(3) 0.0129(3) 0.0018(3) Cl3 0.0234(3) 0.0297(3) 0.0227(3) 0.0038(3) 0.0134(2) 0.0011(3) O1 0.0215(9) 0.0285(10) 0.0227(9) -0.0020(8) 0.0118(8) 0.0004(8) C1 0.0212(11) 0.0219(12) 0.0211(11) -0.0019(10) 0.0106(10) -0.0014(10) C2 0.0218(12) 0.0230(12) 0.0197(11) 0.0007(10) 0.0091(10) 0.0012(10) C3 0.0237(12) 0.0233(13) 0.0240(12) 0.0003(10) 0.0144(10) 0.0002(10) C4 0.0204(11) 0.0214(12) 0.0267(12) -0.0029(10) 0.0128(10) -0.0005(9) C5 0.0219(12) 0.0228(12) 0.0210(11) 0.0003(10) 0.0100(10) 0.0002(10) C6 0.0238(11) 0.0224(12) 0.0217(11) 0.0003(10) 0.0142(10) -0.0018(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Tl1 O1 2.572(2) 5_656 ? Tl1 O1 2.655(2) . ? Cl1 C2 1.753(3) . ? Cl2 C4 1.758(3) . ? Cl3 C6 1.751(3) . ? O1 C1 1.334(3) . ? O1 Tl1 2.572(2) 5_656 ? C1 C6 1.422(4) . ? C1 C2 1.427(4) . ? C2 C3 1.404(4) . ? C3 C4 1.385(4) . ? C3 H3A 0.9300 . ? C4 C5 1.396(4) . ? C5 C6 1.402(4) . ? C5 H5A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Tl1 O1 77.29(8) 5_656 . ? C1 O1 Tl1 111.90(17) . 5_656 ? C1 O1 Tl1 129.99(17) . . ? Tl1 O1 Tl1 102.71(8) 5_656 . ? O1 C1 C6 123.2(2) . . ? O1 C1 C2 124.2(2) . . ? C6 C1 C2 112.5(2) . . ? C3 C2 C1 125.3(3) . . ? C3 C2 Cl1 117.4(2) . . ? C1 C2 Cl1 117.3(2) . . ? C4 C3 C2 118.0(2) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C3 C4 C5 120.8(2) . . ? C3 C4 Cl2 119.9(2) . . ? C5 C4 Cl2 119.3(2) . . ? C4 C5 C6 119.2(2) . . ? C4 C5 H5A 120.4 . . ? C6 C5 H5A 120.4 . . ? C5 C6 C1 124.1(2) . . ? C5 C6 Cl3 117.6(2) . . ? C1 C6 Cl3 118.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Tl1 O1 C1 -133.5(3) 5_656 . . . ? O1 Tl1 O1 Tl1 0.0 5_656 . . 5_656 ? Tl1 O1 C1 C6 -105.6(3) 5_656 . . . ? Tl1 O1 C1 C6 24.7(4) . . . . ? Tl1 O1 C1 C2 71.8(3) 5_656 . . . ? Tl1 O1 C1 C2 -157.9(2) . . . . ? O1 C1 C2 C3 -179.4(3) . . . . ? C6 C1 C2 C3 -1.8(4) . . . . ? O1 C1 C2 Cl1 -0.5(4) . . . . ? C6 C1 C2 Cl1 177.1(2) . . . . ? C1 C2 C3 C4 0.8(5) . . . . ? Cl1 C2 C3 C4 -178.2(2) . . . . ? C2 C3 C4 C5 0.7(4) . . . . ? C2 C3 C4 Cl2 179.8(2) . . . . ? C3 C4 C5 C6 -0.9(4) . . . . ? Cl2 C4 C5 C6 180.0(2) . . . . ? C4 C5 C6 C1 -0.3(5) . . . . ? C4 C5 C6 Cl3 179.1(2) . . . . ? O1 C1 C6 C5 179.2(3) . . . . ? C2 C1 C6 C5 1.5(4) . . . . ? O1 C1 C6 Cl3 -0.2(4) . . . . ? C2 C1 C6 Cl3 -177.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.435 _refine_diff_density_min -0.786 _refine_diff_density_rms 0.159 _publ_section_references ; Bruker (2005). APEX2 softwarwe package, Bruker AXS Inc., 5465, East Cheryl Parkway, Madison, WI 5317. Sheldrick G.M. (1998). SHELXTL v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; The H(C) atom positions were calculated. All hydrogen atoms were refined in isotropic approximation in riding model with with the Uiso(H) parameters equal to 1.2 Ueq(Ci), for methyl groups equal to 1.5 Ueq(Cii), where U(Ci) and U(Cii) are respectively the equivalent thermal parameters of the carbon atoms to which corresponding H atoms are bonded. ; data_9 _database_code_depnum_ccdc_archive 'CCDC 824700' #TrackingRef '- 1-9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 F O Tl' _chemical_formula_weight 315.46 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 10.3447(12) _cell_length_b 19.514(2) _cell_length_c 6.3920(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1290.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2579 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 25.67 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 24.959 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.0462 _exptl_absorpt_correction_T_max 0.1086 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _diffrn_ambient_temperature 298(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 'Bruker APEX area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6427 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.77 _reflns_number_total 1230 _reflns_number_gt 1036 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL(Bruker, 2002)' _computing_publication_material SHELXL97 _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^)+(0.0305P)^2^+2.6669P] 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 SHELXL _refine_ls_extinction_coef 0.0034(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1230 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0740 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 Tl1 Tl 0.86993(3) 0.329803(14) 0.85096(5) 0.03393(19) Uani 1 1 d . . . F1 F 0.2807(6) 0.4694(3) 0.5763(10) 0.088(2) Uani 1 1 d . . . O1 O 0.6321(4) 0.2953(3) 0.9392(9) 0.0375(12) Uani 1 1 d . . . C1 C 0.3675(8) 0.4238(6) 0.6693(13) 0.057(3) Uani 1 1 d . . . C2 C 0.4789(9) 0.4516(4) 0.7531(16) 0.054(2) Uani 1 1 d . . . H2 H 0.4954 0.4984 0.7477 0.064 Uiso 1 1 calc R . . C3 C 0.5637(8) 0.4069(4) 0.8443(12) 0.0389(18) Uani 1 1 d . . . H3 H 0.6390 0.4246 0.9026 0.047 Uiso 1 1 calc R . . C4 C 0.5442(8) 0.3376(4) 0.8547(11) 0.0336(17) Uani 1 1 d . . . C5 C 0.4287(7) 0.3123(4) 0.7710(14) 0.0414(18) Uani 1 1 d . . . H5 H 0.4096 0.2658 0.7793 0.050 Uiso 1 1 calc R . . C6 C 0.3419(8) 0.3574(5) 0.6746(13) 0.048(2) Uani 1 1 d . . . H6 H 0.2664 0.3408 0.6144 0.058 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 Tl1 0.0398(3) 0.0287(2) 0.0333(2) -0.00056(11) -0.00001(11) -0.00276(10) F1 0.091(4) 0.081(5) 0.093(5) 0.001(3) -0.029(4) 0.049(3) O1 0.035(3) 0.031(3) 0.046(3) -0.002(3) -0.003(2) 0.004(2) C1 0.054(6) 0.079(8) 0.037(5) -0.001(4) -0.008(4) 0.031(5) C2 0.080(7) 0.033(5) 0.048(5) -0.002(4) 0.001(5) 0.018(4) C3 0.045(5) 0.032(4) 0.039(4) -0.005(3) -0.005(4) 0.001(3) C4 0.039(4) 0.034(5) 0.028(4) 0.002(3) 0.010(3) 0.007(3) C5 0.038(4) 0.046(5) 0.041(5) 0.003(4) 0.002(4) 0.008(3) C6 0.036(4) 0.057(6) 0.051(6) -0.006(4) -0.009(4) 0.011(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 Tl1 O1 2.506(5) 2_655 ? Tl1 O1 2.612(5) . ? Tl1 O1 2.717(6) 8_755 ? F1 C1 1.396(10) . ? O1 C4 1.342(9) . ? O1 Tl1 2.506(5) 2_655 ? O1 Tl1 2.717(6) 8_756 ? C1 C6 1.323(16) . ? C1 C2 1.381(13) . ? C2 C3 1.367(12) . ? C2 H2 0.9300 . ? C3 C4 1.369(11) . ? C3 H3 0.9300 . ? C4 C5 1.399(12) . ? C5 C6 1.400(12) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Tl1 O1 72.11(17) 2_655 . ? O1 Tl1 O1 88.66(13) 2_655 8_755 ? O1 Tl1 O1 97.94(15) . 8_755 ? C4 O1 Tl1 120.2(4) . 2_655 ? C4 O1 Tl1 113.2(4) . . ? Tl1 O1 Tl1 102.13(17) 2_655 . ? C4 O1 Tl1 103.4(4) . 8_756 ? Tl1 O1 Tl1 117.3(2) 2_655 8_756 ? Tl1 O1 Tl1 98.77(16) . 8_756 ? C6 C1 C2 122.8(8) . . ? C6 C1 F1 120.4(9) . . ? C2 C1 F1 116.9(10) . . ? C3 C2 C1 116.8(9) . . ? C3 C2 H2 121.6 . . ? C1 C2 H2 121.6 . . ? C2 C3 C4 123.8(8) . . ? C2 C3 H3 118.1 . . ? C4 C3 H3 118.1 . . ? O1 C4 C3 121.8(7) . . ? O1 C4 C5 121.1(7) . . ? C3 C4 C5 117.1(7) . . ? C4 C5 C6 119.6(8) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C1 C6 C5 119.9(8) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.77 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.999 _refine_diff_density_min -0.867 _refine_diff_density_rms 0.196 data_2 _database_code_depnum_ccdc_archive 'CCDC 824701' #TrackingRef '- 1-9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H3 Cl2 O Tl' _chemical_formula_sum 'C6 H3 Cl2 O Tl' _chemical_formula_weight 366.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 19.8127(14) _cell_length_b 7.6404(5) _cell_length_c 14.2901(17) _cell_angle_alpha 90.00 _cell_angle_beta 132.817(3) _cell_angle_gamma 90.00 _cell_volume 1586.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.94 _cell_measurement_theta_max 27.96 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 15.715 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1685 _exptl_absorpt_correction_T_max 0.6453 _exptl_absorpt_process_details 'SADABS V2008/1' _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 'Bruker APex II Kappa 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 7012 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.96 _reflns_number_total 3512 _reflns_number_gt 3204 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II kappa' _computing_cell_refinement 'Bruker APEX II kappa' _computing_data_reduction 'Bruker SAINT V7.68A' _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^)+(0.1559P)^2^+29.1181P] 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 0.00 _refine_ls_number_reflns 3512 _refine_ls_number_parameters 184 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0894 _refine_ls_R_factor_gt 0.0831 _refine_ls_wR_factor_ref 0.2133 _refine_ls_wR_factor_gt 0.2073 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.368 _refine_ls_shift/su_mean 0.055 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 O2 O -0.0299(10) 0.651(2) 0.5698(13) 0.022(3) Uani 1 1 d . . . Tl1 Tl -0.04621(6) 0.32660(11) 0.59033(9) 0.0299(3) Uani 1 1 d . . . Tl2 Tl 0.14079(6) 0.66481(10) 0.67537(8) 0.0288(3) Uani 1 1 d . . . O1 O 0.1033(10) 0.334(2) 0.6278(14) 0.023(3) Uani 1 1 d . . . C2 C 0.174(2) 0.143(3) 0.802(3) 0.036(6) Uani 1 1 d . . . H2 H 0.1248 0.1620 0.7986 0.044 Uiso 1 1 calc R . . C1 C 0.1710(17) 0.215(2) 0.717(2) 0.022(4) Uani 1 1 d . . . C4 C 0.324(2) -0.006(3) 0.908(3) 0.039(6) Uani 1 1 d . . . C3 C 0.2506(18) 0.035(3) 0.901(2) 0.029(5) Uani 1 1 d . . . Cl2 Cl 0.4142(6) -0.1383(10) 1.0249(6) 0.0477(19) Uani 1 1 d . . . Cl1 Cl 0.2491(7) -0.0606(11) 1.0068(8) 0.0484(18) Uani 1 1 d . . . C7 C -0.0466(18) 0.756(3) 0.630(2) 0.027(5) Uani 1 1 d . . . C9 C -0.001(2) 0.836(5) 0.829(3) 0.045(7) Uani 1 1 d . . . H9 H 0.0355 0.8248 0.9187 0.054 Uiso 1 1 calc R . . C12 C -0.122(2) 0.861(3) 0.563(3) 0.034(6) Uani 1 1 d . . . H12 H -0.1622 0.8680 0.4730 0.041 Uiso 1 1 calc R . . C8 C 0.019(2) 0.743(3) 0.771(3) 0.041(7) Uani 1 1 d . . . H8 H 0.0728 0.6721 0.8186 0.050 Uiso 1 1 calc R . . Cl4 Cl -0.2380(5) 1.0876(10) 0.5376(7) 0.0413(16) Uani 1 1 d . . . Cl3 Cl -0.1042(7) 1.0675(13) 0.8340(9) 0.057(2) Uani 1 1 d . . . C5 C 0.321(2) 0.080(3) 0.818(3) 0.041(7) Uani 1 1 d . . . H5 H 0.3701 0.0627 0.8208 0.049 Uiso 1 1 calc R . . C6 C 0.249(2) 0.191(4) 0.727(3) 0.042(6) Uani 1 1 d . . . H6 H 0.2497 0.2516 0.6698 0.050 Uiso 1 1 calc R . . C11 C -0.1396(18) 0.960(3) 0.627(3) 0.038(6) Uani 1 1 d . . . C10 C -0.080(2) 0.952(4) 0.755(3) 0.046(7) 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 O2 0.022(7) 0.025(7) 0.017(6) 0.003(6) 0.012(6) 0.006(6) Tl1 0.0385(5) 0.0185(4) 0.0355(5) 0.0020(3) 0.0263(4) -0.0023(3) Tl2 0.0338(5) 0.0195(4) 0.0349(5) -0.0046(3) 0.0240(4) -0.0036(3) O1 0.025(8) 0.015(6) 0.028(7) -0.001(6) 0.018(7) -0.001(6) C2 0.053(16) 0.020(12) 0.040(13) -0.017(10) 0.034(13) -0.010(10) C1 0.031(12) 0.003(7) 0.030(11) -0.006(7) 0.020(10) -0.007(7) C4 0.09(2) 0.018(10) 0.045(13) -0.003(10) 0.057(15) 0.005(12) C3 0.040(14) 0.011(9) 0.016(10) 0.005(6) 0.012(10) -0.006(8) Cl2 0.052(4) 0.040(4) 0.027(3) 0.002(2) 0.017(3) 0.023(3) Cl1 0.058(4) 0.044(4) 0.039(4) 0.013(3) 0.031(3) -0.001(3) C7 0.037(14) 0.031(12) 0.033(13) -0.009(9) 0.031(12) -0.010(10) C9 0.055(17) 0.047(16) 0.046(15) -0.014(13) 0.040(15) 0.006(15) C12 0.066(18) 0.005(10) 0.045(14) -0.004(8) 0.044(15) -0.008(9) C8 0.08(2) 0.016(11) 0.07(2) -0.015(12) 0.07(2) -0.005(12) Cl4 0.046(4) 0.031(3) 0.055(4) 0.010(3) 0.037(4) 0.012(3) Cl3 0.056(5) 0.063(5) 0.060(5) -0.020(4) 0.042(5) 0.005(4) C5 0.06(2) 0.021(12) 0.044(16) 0.015(11) 0.035(16) 0.012(12) C6 0.041(16) 0.051(18) 0.033(13) -0.001(11) 0.025(13) -0.005(12) C11 0.033(14) 0.011(10) 0.056(17) 0.005(9) 0.025(13) 0.005(9) C10 0.057(19) 0.027(13) 0.07(2) -0.017(12) 0.047(17) -0.003(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 O2 C7 1.37(3) . ? O2 Tl1 2.543(18) . ? O2 Tl2 2.578(14) 2_556 ? O2 Tl2 2.606(15) . ? Tl1 O1 2.491(15) 2_556 ? Tl1 O1 2.629(15) . ? Tl2 O2 2.578(14) 2_556 ? Tl2 O1 2.593(17) . ? O1 C1 1.39(3) . ? O1 Tl1 2.491(15) 2_556 ? C2 C1 1.30(4) . ? C2 C3 1.44(4) . ? C2 H2 0.9500 . ? C1 C6 1.46(4) . ? C4 C3 1.41(4) . ? C4 C5 1.42(4) . ? C4 Cl2 1.72(3) . ? C3 Cl1 1.70(2) . ? C7 C12 1.35(4) . ? C7 C8 1.49(4) . ? C9 C8 1.35(3) . ? C9 C10 1.45(5) . ? C9 H9 0.9500 . ? C12 C11 1.41(4) . ? C12 H12 0.9500 . ? C8 H8 0.9500 . ? Cl4 C11 1.73(3) . ? Cl3 C10 1.73(3) . ? C5 C6 1.39(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C11 C10 1.34(5) . ? 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 C7 O2 Tl1 113.4(14) . . ? C7 O2 Tl2 118.8(15) . 2_556 ? Tl1 O2 Tl2 98.0(6) . 2_556 ? C7 O2 Tl2 112.6(14) . . ? Tl1 O2 Tl2 100.9(6) . . ? Tl2 O2 Tl2 110.9(6) 2_556 . ? O1 Tl1 O2 79.6(5) 2_556 . ? O1 Tl1 O1 75.2(5) 2_556 . ? O2 Tl1 O1 77.8(5) . . ? O2 Tl2 O1 77.1(5) 2_556 . ? O2 Tl2 O2 68.9(5) 2_556 . ? O1 Tl2 O2 77.4(5) . . ? C1 O1 Tl1 117.9(13) . 2_556 ? C1 O1 Tl2 118.2(11) . . ? Tl1 O1 Tl2 98.9(5) 2_556 . ? C1 O1 Tl1 115.2(13) . . ? Tl1 O1 Tl1 104.7(5) 2_556 . ? Tl2 O1 Tl1 99.0(5) . . ? C1 C2 C3 120(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.7 . . ? C2 C1 O1 122(2) . . ? C2 C1 C6 119(3) . . ? O1 C1 C6 118(2) . . ? C3 C4 C5 116(3) . . ? C3 C4 Cl2 123.1(18) . . ? C5 C4 Cl2 121(2) . . ? C4 C3 C2 123(2) . . ? C4 C3 Cl1 118.4(18) . . ? C2 C3 Cl1 118(2) . . ? C12 C7 O2 122(2) . . ? C12 C7 C8 121(2) . . ? O2 C7 C8 117(2) . . ? C8 C9 C10 120(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.1 . . ? C7 C12 C11 120(2) . . ? C7 C12 H12 119.9 . . ? C11 C12 H12 119.8 . . ? C9 C8 C7 117(3) . . ? C9 C8 H8 121.5 . . ? C7 C8 H8 121.8 . . ? C6 C5 C4 120(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 121(3) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.3 . . ? C10 C11 C12 119(2) . . ? C10 C11 Cl4 123(2) . . ? C12 C11 Cl4 118(2) . . ? C11 C10 C9 122(3) . . ? C11 C10 Cl3 119(2) . . ? C9 C10 Cl3 118(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O2 Tl1 O1 145.5(16) . . . 2_556 ? Tl2 O2 Tl1 O1 19.3(5) 2_556 . . 2_556 ? Tl2 O2 Tl1 O1 -93.8(5) . . . 2_556 ? C7 O2 Tl1 O1 -137.5(16) . . . . ? Tl2 O2 Tl1 O1 96.3(5) 2_556 . . . ? Tl2 O2 Tl1 O1 -16.9(5) . . . . ? C7 O2 Tl2 O2 -140.8(14) . . . 2_556 ? Tl1 O2 Tl2 O2 98.0(4) . . . 2_556 ? Tl2 O2 Tl2 O2 -5.0(9) 2_556 . . 2_556 ? C7 O2 Tl2 O1 138.3(16) . . . . ? Tl1 O2 Tl2 O1 17.2(5) . . . . ? Tl2 O2 Tl2 O1 -85.8(7) 2_556 . . . ? O2 Tl2 O1 C1 147.6(15) 2_556 . . . ? O2 Tl2 O1 C1 -141.5(15) . . . . ? O2 Tl2 O1 Tl1 19.2(5) 2_556 . . 2_556 ? O2 Tl2 O1 Tl1 90.1(5) . . . 2_556 ? O2 Tl2 O1 Tl1 -87.4(5) 2_556 . . . ? O2 Tl2 O1 Tl1 -16.5(4) . . . . ? O1 Tl1 O1 C1 -133.7(11) 2_556 . . . ? O2 Tl1 O1 C1 144.0(13) . . . . ? O1 Tl1 O1 Tl1 -2.6(8) 2_556 . . 2_556 ? O2 Tl1 O1 Tl1 -84.9(6) . . . 2_556 ? O1 Tl1 O1 Tl2 99.2(4) 2_556 . . . ? O2 Tl1 O1 Tl2 16.9(5) . . . . ? C3 C2 C1 O1 -173.3(19) . . . . ? C3 C2 C1 C6 -3(3) . . . . ? Tl1 O1 C1 C2 -144.1(18) 2_556 . . . ? Tl2 O1 C1 C2 97(2) . . . . ? Tl1 O1 C1 C2 -20(2) . . . . ? Tl1 O1 C1 C6 45(2) 2_556 . . . ? Tl2 O1 C1 C6 -74(2) . . . . ? Tl1 O1 C1 C6 169.9(17) . . . . ? C5 C4 C3 C2 6(4) . . . . ? Cl2 C4 C3 C2 -178.8(19) . . . . ? C5 C4 C3 Cl1 -179(2) . . . . ? Cl2 C4 C3 Cl1 -3(3) . . . . ? C1 C2 C3 C4 -3(3) . . . . ? C1 C2 C3 Cl1 -178.2(18) . . . . ? Tl1 O2 C7 C12 -111(2) . . . . ? Tl2 O2 C7 C12 3(3) 2_556 . . . ? Tl2 O2 C7 C12 134.8(19) . . . . ? Tl1 O2 C7 C8 65(2) . . . . ? Tl2 O2 C7 C8 179.6(16) 2_556 . . . ? Tl2 O2 C7 C8 -48(2) . . . . ? O2 C7 C12 C11 176(2) . . . . ? C8 C7 C12 C11 0(4) . . . . ? C10 C9 C8 C7 -5(5) . . . . ? C12 C7 C8 C9 2(4) . . . . ? O2 C7 C8 C9 -175(3) . . . . ? C3 C4 C5 C6 -3(4) . . . . ? Cl2 C4 C5 C6 -178(2) . . . . ? C4 C5 C6 C1 -3(4) . . . . ? C2 C1 C6 C5 6(4) . . . . ? O1 C1 C6 C5 177(2) . . . . ? C7 C12 C11 C10 2(4) . . . . ? C7 C12 C11 Cl4 -178.3(19) . . . . ? C12 C11 C10 C9 -5(5) . . . . ? Cl4 C11 C10 C9 175(3) . . . . ? C12 C11 C10 Cl3 -178(2) . . . . ? Cl4 C11 C10 Cl3 2(4) . . . . ? C8 C9 C10 C11 6(5) . . . . ? C8 C9 C10 Cl3 179(3) . . . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 27.96 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 9.076 _refine_diff_density_min -5.043 _refine_diff_density_rms 0.702 data_3 _database_code_depnum_ccdc_archive 'CCDC 824702' #TrackingRef '- 1-9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H3 Cl2 O Tl' _chemical_formula_sum 'C6 H3 Cl2 O Tl' _chemical_formula_weight 366.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.8883(4) _cell_length_b 19.8849(19) _cell_length_c 9.7499(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.920(5) _cell_angle_gamma 90.00 _cell_volume 751.07(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4747 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.66 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.354 _exptl_crystal_size_mid 0.065 _exptl_crystal_size_min 0.063 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 22.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2586 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS V2008/1' _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 'Bruker APex II Kappa 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 6510 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.66 _reflns_number_total 1740 _reflns_number_gt 1606 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II kappa' _computing_cell_refinement 'Bruker APEX II kappa' _computing_data_reduction 'Bruker SAINT V7.68A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0135P)^2^+0.2801P] 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 1710 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0168 _refine_ls_R_factor_gt 0.0150 _refine_ls_wR_factor_ref 0.0353 _refine_ls_wR_factor_gt 0.0347 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.002 _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 Tl1 Tl 0.74455(3) -0.073980(5) 0.595186(11) 0.01346(5) Uani 1 1 d . . . Cl1 Cl 0.7042(2) 0.29279(4) 0.74748(9) 0.02281(18) Uani 1 1 d . . . Cl2 Cl 1.21830(19) -0.00198(4) 0.83976(8) 0.01816(16) Uani 1 1 d . . . O1 O 0.8237(6) 0.05170(11) 0.5860(2) 0.0150(4) Uani 1 1 d . . . C1 C 0.8856(8) 0.09653(15) 0.6867(3) 0.0133(6) Uani 1 1 d . . . C2 C 0.7809(7) 0.16401(15) 0.6694(3) 0.0150(6) Uani 1 1 d . . . H2 H 0.6606 0.1780 0.5854 0.018 Uiso 1 1 calc R . . C3 C 0.8526(8) 0.20993(15) 0.7744(3) 0.0161(6) Uani 1 1 d . . . C4 C 1.0313(8) 0.19322(17) 0.8985(3) 0.0191(7) Uani 1 1 d . . . H4 H 1.0763 0.2257 0.9691 0.023 Uiso 1 1 calc R . . C5 C 1.1429(8) 0.12708(17) 0.9162(3) 0.0170(6) Uani 1 1 d . . . H5 H 1.2707 0.1140 0.9993 0.020 Uiso 1 1 calc R . . C6 C 1.0682(8) 0.08051(15) 0.8130(3) 0.0143(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 Tl1 0.01431(8) 0.01109(8) 0.01477(8) 0.00192(4) 0.00002(5) -0.00088(4) Cl1 0.0239(4) 0.0134(4) 0.0312(5) -0.0070(3) 0.0031(3) 0.0004(3) Cl2 0.0187(4) 0.0190(4) 0.0162(4) 0.0010(3) -0.0017(3) 0.0034(3) O1 0.0216(11) 0.0124(11) 0.0107(10) -0.0031(8) -0.0005(8) -0.0007(9) C1 0.0125(14) 0.0124(14) 0.0154(15) -0.0015(12) 0.0030(11) -0.0032(11) C2 0.0120(14) 0.0153(15) 0.0179(16) -0.0002(12) 0.0034(12) 0.0000(12) C3 0.0150(15) 0.0106(15) 0.0235(16) -0.0027(12) 0.0062(12) -0.0002(11) C4 0.0166(16) 0.0205(17) 0.0210(17) -0.0091(13) 0.0051(12) -0.0051(13) C5 0.0174(15) 0.0215(17) 0.0116(15) -0.0027(12) -0.0024(11) -0.0038(13) C6 0.0129(15) 0.0154(16) 0.0151(16) 0.0014(12) 0.0043(12) 0.0004(11) _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 Tl1 O1 2.521(2) . ? Tl1 O1 2.577(2) 3_756 ? Tl1 O1 2.744(2) 3_656 ? Cl1 C3 1.758(3) . ? Cl2 C6 1.753(3) . ? O1 C1 1.333(4) . ? O1 Tl1 2.577(2) 3_756 ? O1 Tl1 2.744(2) 3_656 ? C1 C6 1.404(4) . ? C1 C2 1.408(4) . ? C2 C3 1.382(4) . ? C3 C4 1.383(5) . ? C4 C5 1.391(5) . ? C5 C6 1.380(4) . ? 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 Tl1 O1 73.53(8) . 3_756 ? O1 Tl1 O1 84.89(7) . 3_656 ? O1 Tl1 O1 93.84(7) 3_756 3_656 ? C1 O1 Tl1 130.67(19) . . ? C1 O1 Tl1 107.64(18) . 3_756 ? Tl1 O1 Tl1 106.47(8) . 3_756 ? C1 O1 Tl1 116.80(19) . 3_656 ? Tl1 O1 Tl1 95.11(7) . 3_656 ? Tl1 O1 Tl1 93.84(7) 3_756 3_656 ? O1 C1 C6 122.7(3) . . ? O1 C1 C2 121.1(3) . . ? C6 C1 C2 116.1(3) . . ? C3 C2 C1 120.2(3) . . ? C2 C3 C4 122.9(3) . . ? C2 C3 Cl1 117.7(2) . . ? C4 C3 Cl1 119.3(2) . . ? C3 C4 C5 117.6(3) . . ? C6 C5 C4 120.0(3) . . ? C5 C6 C1 123.1(3) . . ? C5 C6 Cl2 118.2(3) . . ? C1 C6 Cl2 118.7(2) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.66 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.520 _refine_diff_density_min -0.931 _refine_diff_density_rms 0.143 data_7 _database_code_depnum_ccdc_archive 'CCDC 824703' #TrackingRef '- 1-9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 Cl4 O4 Tl4' _chemical_formula_sum 'C24 H16 Cl4 O4 Tl4' _chemical_formula_weight 1327.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'I -4' _symmetry_space_group_name_Hall 'I -4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 14.1678(7) _cell_length_b 14.1678(7) _cell_length_c 7.0565(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1416.43(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3204 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 31.63 _exptl_crystal_description bolck _exptl_crystal_colour colourless _exptl_crystal_size_max 0.284 _exptl_crystal_size_mid 0.193 _exptl_crystal_size_min 0.073 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.113 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 23.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1864 _exptl_absorpt_correction_T_max 0.7463 _exptl_absorpt_process_details 'SADABS V2008/1' _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 'Bruker APex II Kappa 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 3740 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0539 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 31.64 _reflns_number_total 2151 _reflns_number_gt 2083 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II kappa' _computing_cell_refinement 'Bruker APEX II kappa' _computing_data_reduction 'Bruker SAINT V7.68A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0331P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(15) _refine_ls_number_reflns 2151 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 Tl1 Tl 0.546948(17) 0.633805(17) 0.30193(4) 0.01100(8) Uani 1 1 d . . . Cl1 Cl 0.06079(12) 0.63797(13) -0.1191(3) 0.0157(4) Uani 1 1 d . . . O1 O 0.3962(3) 0.5385(4) 0.3354(8) 0.0122(11) Uani 1 1 d . . . C3 C 0.1698(5) 0.5189(5) 0.0864(13) 0.0131(13) Uani 1 1 d . . . H3 H 0.1222 0.4731 0.0633 0.016 Uiso 1 1 calc R . . C2 C 0.2294(5) 0.6772(5) 0.0476(10) 0.0125(13) Uani 1 1 d . . . H2 H 0.2228 0.7390 -0.0029 0.015 Uiso 1 1 calc R . . C1 C 0.1602(5) 0.6088(5) 0.0147(12) 0.0129(14) Uani 1 1 d . . . C6 C 0.2479(5) 0.4953(5) 0.1908(13) 0.0131(13) Uani 1 1 d . . . H6 H 0.2536 0.4331 0.2394 0.016 Uiso 1 1 calc R . . C5 C 0.3076(5) 0.6536(5) 0.1547(10) 0.0138(15) Uani 1 1 d . . . H5 H 0.3540 0.7005 0.1793 0.017 Uiso 1 1 calc R . . C7 C 0.3207(5) 0.5624(5) 0.2283(10) 0.0097(13) 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 Tl1 0.01069(13) 0.01133(13) 0.01099(12) 0.00275(10) 0.00245(10) 0.00138(9) Cl1 0.0145(7) 0.0173(8) 0.0154(9) -0.0008(7) -0.0068(7) 0.0040(6) O1 0.008(2) 0.019(2) 0.009(3) -0.001(2) -0.0002(18) 0.0022(17) C3 0.010(3) 0.013(3) 0.016(4) 0.002(3) 0.001(3) -0.001(2) C2 0.017(3) 0.011(3) 0.010(4) -0.004(3) 0.000(3) 0.005(2) C1 0.009(3) 0.015(3) 0.015(4) -0.001(3) -0.005(3) 0.005(3) C6 0.020(3) 0.011(3) 0.008(3) 0.002(3) -0.003(3) 0.001(2) C5 0.013(3) 0.016(3) 0.012(4) -0.004(3) 0.002(3) -0.002(2) C7 0.008(3) 0.020(3) 0.002(3) -0.003(2) 0.000(2) 0.002(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 Tl1 O1 2.538(5) . ? Tl1 O1 2.582(5) 2_665 ? Tl1 O1 2.597(6) 3_566 ? Cl1 C1 1.745(7) . ? O1 C7 1.352(8) . ? O1 Tl1 2.582(5) 2_665 ? O1 Tl1 2.597(6) 4_656 ? C3 C6 1.371(10) . ? C3 C1 1.378(10) . ? C3 H3 0.9500 . ? C2 C5 1.382(10) . ? C2 C1 1.398(10) . ? C2 H2 0.9500 . ? C6 C7 1.428(10) . ? C6 H6 0.9500 . ? C5 C7 1.405(10) . ? C5 H5 0.9500 . ? 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 Tl1 O1 75.60(18) . 2_665 ? O1 Tl1 O1 77.44(19) . 3_566 ? O1 Tl1 O1 76.68(19) 2_665 3_566 ? C7 O1 Tl1 118.7(4) . . ? C7 O1 Tl1 115.6(4) . 2_665 ? Tl1 O1 Tl1 103.40(18) . 2_665 ? C7 O1 Tl1 114.2(4) . 4_656 ? Tl1 O1 Tl1 101.82(19) . 4_656 ? Tl1 O1 Tl1 100.64(19) 2_665 4_656 ? C6 C3 C1 120.1(7) . . ? C6 C3 H3 119.9 . . ? C1 C3 H3 119.9 . . ? C5 C2 C1 119.0(7) . . ? C5 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C3 C1 C2 120.7(7) . . ? C3 C1 Cl1 119.8(6) . . ? C2 C1 Cl1 119.5(6) . . ? C3 C6 C7 121.4(6) . . ? C3 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C2 C5 C7 122.0(7) . . ? C2 C5 H5 119.0 . . ? C7 C5 H5 119.0 . . ? O1 C7 C5 122.8(6) . . ? O1 C7 C6 120.5(6) . . ? C5 C7 C6 116.6(7) . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.821 _refine_diff_density_min -3.315 _refine_diff_density_rms 0.337 data_8 _database_code_depnum_ccdc_archive 'CCDC 824704' #TrackingRef '- 1-9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 I4 O4 Tl4' _chemical_formula_sum 'C24 H16 I4 O4 Tl4' _chemical_formula_weight 1693.49 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' Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_space_group_name_Hall 'P 2yb ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.0853(5) _cell_length_b 15.7875(8) _cell_length_c 10.3100(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.334(2) _cell_angle_gamma 90.00 _cell_volume 1590.47(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.035 _exptl_crystal_size_mid 0.243 _exptl_crystal_size_max 0.265 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.536 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 24.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3003 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS V2008/1' _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 'Bruker APex II Kappa 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 13900 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0667 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.58 _reflns_number_total 6659 _reflns_number_gt 6190 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II kappa' _computing_cell_refinement 'Bruker APEX II kappa' _computing_data_reduction 'Bruker SAINT V7.68A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 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 0.025(4) _refine_ls_number_reflns 6659 _refine_ls_number_parameters 326 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0582 _refine_ls_wR_factor_gt 0.0573 _refine_ls_goodness_of_fit_ref 0.853 _refine_ls_restrained_S_all 0.853 _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 Tl1 Tl 0.12595(3) 0.15259(2) 0.47759(3) 0.02194(8) Uani 1 1 d . . . Tl2 Tl 0.32610(4) 0.15899(2) 0.20087(4) 0.02480(8) Uani 1 1 d . . . Tl3 Tl 0.50139(4) 0.07366(2) 0.59559(4) 0.02487(8) Uani 1 1 d . . . Tl4 Tl 0.46247(3) 0.31344(2) 0.49631(3) 0.02049(8) Uani 1 1 d . . . I5 I -0.20384(6) 0.54426(4) 0.15509(6) 0.02653(14) Uani 1 1 d . . . I6 I 0.96616(6) 0.06524(4) 0.10797(7) 0.03299(15) Uani 1 1 d . . . I7 I 0.41359(6) 0.40794(4) 1.14855(7) 0.03345(15) Uani 1 1 d . . . I8 I 0.14626(7) -0.31903(4) 0.26555(9) 0.0433(2) Uani 1 1 d . . . O1 O 0.2296(5) 0.2571(4) 0.3434(6) 0.0212(13) Uani 1 1 d . . . O2 O 0.2967(6) 0.0604(3) 0.3924(6) 0.0250(14) Uani 1 1 d . . . O3 O 0.5358(6) 0.1754(4) 0.4191(7) 0.0267(15) Uani 1 1 d . . . O4 O 0.3580(6) 0.1961(4) 0.6287(6) 0.0222(13) Uani 1 1 d . . . C1 C 0.6327(9) 0.1532(6) 0.3549(9) 0.0255(19) Uani 1 1 d . . . C2 C 0.7018(8) 0.2116(6) 0.3011(9) 0.023(2) Uani 1 1 d . . . H2 H 0.6842 0.2699 0.3124 0.028 Uiso 1 1 calc R . . C3 C 0.7979(9) 0.1898(6) 0.2297(10) 0.029(2) Uani 1 1 d . . . H3 H 0.8434 0.2321 0.1914 0.035 Uiso 1 1 calc R . . C4 C 0.8250(9) 0.1031(6) 0.2164(10) 0.026(2) Uani 1 1 d . . . C5 C 0.3648(8) 0.2354(5) 0.7463(8) 0.0162(17) Uani 1 1 d . . . C6 C 0.4818(9) 0.2280(6) 0.8519(9) 0.029(2) Uani 1 1 d . . . H6 H 0.5532 0.1903 0.8448 0.035 Uiso 1 1 calc R . . C7 C 0.4932(10) 0.2753(7) 0.9663(10) 0.036(3) Uani 1 1 d . . . H7 H 0.5744 0.2721 1.0364 0.044 Uiso 1 1 calc R . . C8 C 0.3865(9) 0.3277(6) 0.9796(9) 0.026(2) Uani 1 1 d . . . C9 C 0.2663(10) 0.3310(6) 0.8817(10) 0.029(2) Uani 1 1 d . . . H9 H 0.1917 0.3648 0.8923 0.035 Uiso 1 1 calc R . . C10 C 0.2919(9) -0.0629(5) 0.2527(9) 0.027(2) Uani 1 1 d . . . H10 H 0.3318 -0.0322 0.1928 0.032 Uiso 1 1 calc R . . C11 C 0.2679(9) -0.0203(6) 0.3671(10) 0.024(2) Uani 1 1 d . . . C12 C 0.2090(8) -0.0703(6) 0.4533(9) 0.025(2) Uani 1 1 d . . . H12 H 0.1951 -0.0460 0.5332 0.030 Uiso 1 1 calc R . . C13 C -0.0509(8) 0.4508(5) 0.2154(9) 0.0176(17) Uani 1 1 d . . . C14 C -0.0330(8) 0.3891(5) 0.1255(8) 0.0189(18) Uani 1 1 d . . . H14 H -0.0862 0.3906 0.0355 0.023 Uiso 1 1 calc R . . C15 C 0.1981(8) -0.1922(6) 0.3107(10) 0.028(2) Uani 1 1 d . . . C17 C 0.1409(8) 0.3215(5) 0.2988(9) 0.0198(18) Uani 1 1 d . . . C18 C 0.0628(8) 0.3246(5) 0.1670(9) 0.0231(19) Uani 1 1 d . . . H18 H 0.0748 0.2826 0.1049 0.028 Uiso 1 1 calc R . . C19 C 0.2575(9) 0.2834(6) 0.7665(10) 0.027(2) Uani 1 1 d . . . H19 H 0.1742 0.2840 0.6989 0.032 Uiso 1 1 calc R . . C20 C 0.6602(13) 0.0672(6) 0.3383(12) 0.047(3) Uani 1 1 d . . . H20 H 0.6114 0.0250 0.3731 0.057 Uiso 1 1 calc R . . C21 C 0.7577(12) 0.0435(6) 0.2716(12) 0.048(3) Uani 1 1 d . . . H21 H 0.7781 -0.0148 0.2643 0.058 Uiso 1 1 calc R . . C22 C 0.1717(9) -0.1538(6) 0.4231(10) 0.029(2) Uani 1 1 d . . . H22 H 0.1279 -0.1850 0.4794 0.035 Uiso 1 1 calc R . . C23 C 0.1240(9) 0.3860(5) 0.3874(10) 0.0224(19) Uani 1 1 d . . . H23 H 0.1769 0.3857 0.4776 0.027 Uiso 1 1 calc R . . C24 C 0.0281(8) 0.4513(6) 0.3420(10) 0.026(2) Uani 1 1 d . . . H24 H 0.0190 0.4959 0.4010 0.032 Uiso 1 1 calc R . . C25 C 0.2598(9) -0.1456(6) 0.2267(9) 0.025(2) Uani 1 1 d . . . H25 H 0.2794 -0.1719 0.1507 0.030 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 Tl1 0.02482(16) 0.02125(16) 0.01972(17) 0.00023(15) 0.00543(13) -0.00168(14) Tl2 0.03630(19) 0.02063(16) 0.01912(18) 0.00028(15) 0.01002(14) -0.00060(16) Tl3 0.03054(19) 0.01966(16) 0.02472(19) 0.00438(15) 0.00741(15) 0.00251(14) Tl4 0.02404(16) 0.01743(15) 0.02031(17) -0.00128(14) 0.00607(13) -0.00018(14) I5 0.0228(3) 0.0264(3) 0.0298(4) 0.0060(3) 0.0053(3) 0.0027(2) I6 0.0293(3) 0.0412(4) 0.0314(4) -0.0051(3) 0.0130(3) 0.0069(3) I7 0.0410(3) 0.0400(4) 0.0223(3) -0.0105(3) 0.0134(3) -0.0149(3) I8 0.0337(4) 0.0276(3) 0.0663(6) -0.0194(3) 0.0082(4) -0.0086(3) O1 0.027(3) 0.023(3) 0.012(3) 0.009(2) 0.003(3) 0.001(2) O2 0.035(3) 0.017(3) 0.026(4) 0.003(3) 0.013(3) 0.001(3) O3 0.030(3) 0.022(3) 0.035(4) 0.002(3) 0.020(3) 0.005(3) O4 0.029(3) 0.026(3) 0.011(3) 0.001(3) 0.005(2) 0.000(3) C1 0.035(5) 0.021(4) 0.025(5) -0.001(4) 0.016(4) -0.002(4) C2 0.024(4) 0.019(4) 0.026(5) -0.009(4) 0.005(4) -0.004(4) C3 0.022(5) 0.028(5) 0.042(6) 0.001(5) 0.013(4) -0.005(4) C4 0.022(4) 0.034(5) 0.022(5) 0.002(4) 0.004(4) 0.003(4) C5 0.021(4) 0.015(4) 0.010(4) -0.002(3) -0.003(3) -0.002(3) C6 0.022(4) 0.050(6) 0.014(5) -0.004(4) 0.003(4) 0.006(4) C7 0.025(5) 0.066(7) 0.014(5) -0.011(5) -0.002(4) -0.012(5) C8 0.037(5) 0.031(5) 0.010(4) -0.005(4) 0.009(4) -0.009(4) C9 0.037(5) 0.027(5) 0.026(5) -0.008(4) 0.013(4) 0.001(4) C10 0.042(5) 0.020(4) 0.018(5) 0.004(4) 0.007(4) 0.011(4) C11 0.025(5) 0.024(5) 0.020(5) 0.011(4) 0.001(4) 0.002(4) C12 0.029(5) 0.024(4) 0.023(5) -0.003(4) 0.009(4) 0.004(4) C13 0.021(4) 0.015(4) 0.018(5) 0.004(3) 0.007(3) -0.005(3) C14 0.020(4) 0.023(4) 0.013(4) 0.005(3) 0.003(3) -0.009(3) C15 0.022(4) 0.022(4) 0.034(6) -0.005(4) -0.005(4) 0.000(4) C17 0.021(4) 0.017(4) 0.025(5) 0.009(4) 0.011(3) -0.004(4) C18 0.021(4) 0.025(5) 0.025(5) 0.000(4) 0.007(4) -0.004(4) C19 0.028(5) 0.030(5) 0.021(5) -0.003(4) 0.002(4) 0.001(4) C20 0.085(9) 0.019(5) 0.056(8) 0.004(5) 0.053(7) -0.005(5) C21 0.078(8) 0.022(5) 0.059(8) -0.005(5) 0.044(7) 0.011(5) C22 0.030(5) 0.027(5) 0.028(6) 0.004(4) 0.004(4) 0.003(4) C23 0.022(4) 0.020(4) 0.026(5) 0.007(4) 0.006(4) 0.000(3) C24 0.023(4) 0.030(5) 0.022(5) 0.000(4) -0.001(4) 0.003(4) C25 0.028(5) 0.028(5) 0.020(5) 0.002(4) 0.005(4) 0.013(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 Tl1 O1 2.538(6) . ? Tl1 O4 2.563(6) . ? Tl1 O2 2.570(6) . ? Tl2 O1 2.493(6) . ? Tl2 O2 2.589(6) . ? Tl2 O3 2.692(7) . ? Tl3 O4 2.488(6) . ? Tl3 O3 2.514(6) . ? Tl3 O2 2.559(6) . ? Tl4 O3 2.495(6) . ? Tl4 O1 2.638(5) . ? Tl4 O4 2.668(6) . ? I5 C13 2.114(8) . ? I6 C4 2.103(9) . ? I7 C8 2.116(9) . ? I8 C15 2.092(9) . ? O1 C17 1.357(10) . ? O2 C11 1.318(11) . ? O3 C1 1.355(10) . ? O4 C5 1.350(10) . ? C1 C2 1.355(12) . ? C1 C20 1.405(13) . ? C2 C3 1.397(12) . ? C2 H2 0.9500 . ? C3 C4 1.409(12) . ? C3 H3 0.9500 . ? C4 C21 1.365(14) . ? C5 C19 1.378(12) . ? C5 C6 1.398(11) . ? C6 C7 1.376(13) . ? C6 H6 0.9500 . ? C7 C8 1.392(13) . ? C7 H7 0.9500 . ? C8 C9 1.373(13) . ? C9 C19 1.390(13) . ? C9 H9 0.9500 . ? C10 C25 1.356(12) . ? C10 C11 1.429(13) . ? C10 H10 0.9500 . ? C11 C12 1.424(13) . ? C12 C22 1.385(12) . ? C12 H12 0.9500 . ? C13 C24 1.351(12) . ? C13 C14 1.387(12) . ? C14 C18 1.395(11) . ? C14 H14 0.9500 . ? C15 C22 1.391(13) . ? C15 C25 1.394(13) . ? C17 C18 1.393(12) . ? C17 C23 1.407(13) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.384(14) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.411(12) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? 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 Tl1 O4 73.73(18) . . ? O1 Tl1 O2 77.32(18) . . ? O4 Tl1 O2 76.76(19) . . ? O1 Tl2 O2 77.79(18) . . ? O1 Tl2 O3 77.77(17) . . ? O2 Tl2 O3 68.57(18) . . ? O4 Tl3 O3 78.00(19) . . ? O4 Tl3 O2 78.30(19) . . ? O3 Tl3 O2 71.82(19) . . ? O3 Tl4 O1 78.8(2) . . ? O3 Tl4 O4 75.06(19) . . ? O1 Tl4 O4 70.45(17) . . ? C17 O1 Tl2 125.9(5) . . ? C17 O1 Tl1 110.3(4) . . ? Tl2 O1 Tl1 101.0(2) . . ? C17 O1 Tl4 111.3(5) . . ? Tl2 O1 Tl4 98.17(19) . . ? Tl1 O1 Tl4 108.6(2) . . ? C11 O2 Tl3 109.6(5) . . ? C11 O2 Tl1 118.8(5) . . ? Tl3 O2 Tl1 98.5(2) . . ? C11 O2 Tl2 119.4(5) . . ? Tl3 O2 Tl2 110.7(2) . . ? Tl1 O2 Tl2 97.65(19) . . ? C1 O3 Tl4 133.5(5) . . ? C1 O3 Tl3 115.7(5) . . ? Tl4 O3 Tl3 102.8(2) . . ? C1 O3 Tl2 94.5(5) . . ? Tl4 O3 Tl2 96.72(19) . . ? Tl3 O3 Tl2 108.8(2) . . ? C5 O4 Tl3 125.4(5) . . ? C5 O4 Tl1 120.4(5) . . ? Tl3 O4 Tl1 100.5(2) . . ? C5 O4 Tl4 101.6(5) . . ? Tl3 O4 Tl4 98.8(2) . . ? Tl1 O4 Tl4 107.0(2) . . ? C2 C1 O3 122.1(8) . . ? C2 C1 C20 118.1(8) . . ? O3 C1 C20 119.8(8) . . ? C1 C2 C3 122.9(8) . . ? C1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C2 C3 C4 117.9(8) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C21 C4 C3 120.0(9) . . ? C21 C4 I6 119.8(7) . . ? C3 C4 I6 120.1(7) . . ? O4 C5 C19 121.4(7) . . ? O4 C5 C6 120.4(7) . . ? C19 C5 C6 118.1(8) . . ? C7 C6 C5 119.8(8) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 120.3(9) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.9(8) . . ? C9 C8 I7 119.5(7) . . ? C7 C8 I7 119.5(7) . . ? C8 C9 C19 117.7(8) . . ? C8 C9 H9 121.1 . . ? C19 C9 H9 121.1 . . ? C25 C10 C11 122.4(9) . . ? C25 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? O2 C11 C12 121.2(9) . . ? O2 C11 C10 123.0(8) . . ? C12 C11 C10 115.8(8) . . ? C22 C12 C11 121.3(9) . . ? C22 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C24 C13 C14 120.4(8) . . ? C24 C13 I5 119.6(7) . . ? C14 C13 I5 120.0(6) . . ? C13 C14 C18 120.2(8) . . ? C13 C14 H14 119.9 . . ? C18 C14 H14 119.9 . . ? C22 C15 C25 119.6(9) . . ? C22 C15 I8 120.9(7) . . ? C25 C15 I8 119.5(7) . . ? O1 C17 C18 121.6(8) . . ? O1 C17 C23 119.9(8) . . ? C18 C17 C23 118.5(8) . . ? C17 C18 C14 120.4(8) . . ? C17 C18 H18 119.8 . . ? C14 C18 H18 119.8 . . ? C5 C19 C9 122.7(8) . . ? C5 C19 H19 118.7 . . ? C9 C19 H19 118.7 . . ? C21 C20 C1 120.5(9) . . ? C21 C20 H20 119.7 . . ? C1 C20 H20 119.7 . . ? C4 C21 C20 120.6(9) . . ? C4 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C12 C22 C15 120.3(9) . . ? C12 C22 H22 119.8 . . ? C15 C22 H22 119.8 . . ? C24 C23 C17 119.8(8) . . ? C24 C23 H23 120.1 . . ? C17 C23 H23 120.1 . . ? C13 C24 C23 120.6(9) . . ? C13 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C10 C25 C15 120.4(9) . . ? C10 C25 H25 119.8 . . ? C15 C25 H25 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Tl2 O1 C17 -144.3(6) . . . . ? O3 Tl2 O1 C17 145.3(6) . . . . ? O2 Tl2 O1 Tl1 -19.12(19) . . . . ? O3 Tl2 O1 Tl1 -89.51(19) . . . . ? O2 Tl2 O1 Tl4 91.8(2) . . . . ? O3 Tl2 O1 Tl4 21.39(17) . . . . ? O4 Tl1 O1 C17 -125.9(5) . . . . ? O2 Tl1 O1 C17 154.4(5) . . . . ? O4 Tl1 O1 Tl2 99.0(2) . . . . ? O2 Tl1 O1 Tl2 19.30(19) . . . . ? O4 Tl1 O1 Tl4 -3.6(2) . . . . ? O2 Tl1 O1 Tl4 -83.3(2) . . . . ? O3 Tl4 O1 C17 -156.9(5) . . . . ? O4 Tl4 O1 C17 125.2(5) . . . . ? O3 Tl4 O1 Tl2 -23.09(19) . . . . ? O4 Tl4 O1 Tl2 -101.1(2) . . . . ? O3 Tl4 O1 Tl1 81.5(2) . . . . ? O4 Tl4 O1 Tl1 3.6(2) . . . . ? O4 Tl3 O2 C11 -143.2(6) . . . . ? O3 Tl3 O2 C11 135.8(6) . . . . ? O4 Tl3 O2 Tl1 -18.47(18) . . . . ? O3 Tl3 O2 Tl1 -99.5(2) . . . . ? O4 Tl3 O2 Tl2 83.1(2) . . . . ? O3 Tl3 O2 Tl2 2.0(2) . . . . ? O1 Tl1 O2 C11 -148.1(6) . . . . ? O4 Tl1 O2 C11 135.9(6) . . . . ? O1 Tl1 O2 Tl3 94.02(19) . . . . ? O4 Tl1 O2 Tl3 18.02(18) . . . . ? O1 Tl1 O2 Tl2 -18.37(18) . . . . ? O4 Tl1 O2 Tl2 -94.4(2) . . . . ? O1 Tl2 O2 C11 148.0(6) . . . . ? O3 Tl2 O2 C11 -130.5(6) . . . . ? O1 Tl2 O2 Tl3 -83.4(2) . . . . ? O3 Tl2 O2 Tl3 -1.91(19) . . . . ? O1 Tl2 O2 Tl1 18.68(18) . . . . ? O3 Tl2 O2 Tl1 100.2(2) . . . . ? O1 Tl4 O3 C1 124.0(8) . . . . ? O4 Tl4 O3 C1 -163.4(8) . . . . ? O1 Tl4 O3 Tl3 -89.9(2) . . . . ? O4 Tl4 O3 Tl3 -17.36(19) . . . . ? O1 Tl4 O3 Tl2 21.22(17) . . . . ? O4 Tl4 O3 Tl2 93.8(2) . . . . ? O4 Tl3 O3 C1 171.7(6) . . . . ? O2 Tl3 O3 C1 -106.8(6) . . . . ? O4 Tl3 O3 Tl4 18.4(2) . . . . ? O2 Tl3 O3 Tl4 99.9(2) . . . . ? O4 Tl3 O3 Tl2 -83.4(2) . . . . ? O2 Tl3 O3 Tl2 -1.91(19) . . . . ? O1 Tl2 O3 C1 -157.4(5) . . . . ? O2 Tl2 O3 C1 121.1(5) . . . . ? O1 Tl2 O3 Tl4 -22.61(19) . . . . ? O2 Tl2 O3 Tl4 -104.1(2) . . . . ? O1 Tl2 O3 Tl3 83.4(2) . . . . ? O2 Tl2 O3 Tl3 1.93(19) . . . . ? O3 Tl3 O4 C5 -128.0(6) . . . . ? O2 Tl3 O4 C5 158.3(6) . . . . ? O3 Tl3 O4 Tl1 92.3(2) . . . . ? O2 Tl3 O4 Tl1 18.64(19) . . . . ? O3 Tl3 O4 Tl4 -16.95(19) . . . . ? O2 Tl3 O4 Tl4 -90.6(2) . . . . ? O1 Tl1 O4 C5 118.6(6) . . . . ? O2 Tl1 O4 C5 -161.0(6) . . . . ? O1 Tl1 O4 Tl3 -99.1(2) . . . . ? O2 Tl1 O4 Tl3 -18.68(19) . . . . ? O1 Tl1 O4 Tl4 3.6(2) . . . . ? O2 Tl1 O4 Tl4 84.0(2) . . . . ? O3 Tl4 O4 C5 146.3(5) . . . . ? O1 Tl4 O4 C5 -130.5(5) . . . . ? O3 Tl4 O4 Tl3 17.31(19) . . . . ? O1 Tl4 O4 Tl3 100.4(2) . . . . ? O3 Tl4 O4 Tl1 -86.6(2) . . . . ? O1 Tl4 O4 Tl1 -3.5(2) . . . . ? Tl4 O3 C1 C2 -9.7(14) . . . . ? Tl3 O3 C1 C2 -152.6(7) . . . . ? Tl2 O3 C1 C2 94.0(9) . . . . ? Tl4 O3 C1 C20 172.7(7) . . . . ? Tl3 O3 C1 C20 29.8(11) . . . . ? Tl2 O3 C1 C20 -83.6(9) . . . . ? O3 C1 C2 C3 -177.2(9) . . . . ? C20 C1 C2 C3 0.4(15) . . . . ? C1 C2 C3 C4 -1.4(15) . . . . ? C2 C3 C4 C21 0.4(15) . . . . ? C2 C3 C4 I6 179.1(7) . . . . ? Tl3 O4 C5 C19 -159.3(6) . . . . ? Tl1 O4 C5 C19 -26.8(10) . . . . ? Tl4 O4 C5 C19 91.0(8) . . . . ? Tl3 O4 C5 C6 20.3(11) . . . . ? Tl1 O4 C5 C6 152.9(7) . . . . ? Tl4 O4 C5 C6 -89.4(8) . . . . ? O4 C5 C6 C7 173.3(9) . . . . ? C19 C5 C6 C7 -7.1(14) . . . . ? C5 C6 C7 C8 2.8(15) . . . . ? C6 C7 C8 C9 2.4(15) . . . . ? C6 C7 C8 I7 -174.6(8) . . . . ? C7 C8 C9 C19 -3.0(14) . . . . ? I7 C8 C9 C19 173.9(7) . . . . ? Tl3 O2 C11 C12 71.0(9) . . . . ? Tl1 O2 C11 C12 -41.0(10) . . . . ? Tl2 O2 C11 C12 -159.9(6) . . . . ? Tl3 O2 C11 C10 -109.5(8) . . . . ? Tl1 O2 C11 C10 138.6(7) . . . . ? Tl2 O2 C11 C10 19.6(11) . . . . ? C25 C10 C11 O2 -178.9(8) . . . . ? C25 C10 C11 C12 0.6(13) . . . . ? O2 C11 C12 C22 176.4(8) . . . . ? C10 C11 C12 C22 -3.1(13) . . . . ? C24 C13 C14 C18 2.8(12) . . . . ? I5 C13 C14 C18 -176.5(6) . . . . ? Tl2 O1 C17 C18 19.4(10) . . . . ? Tl1 O1 C17 C18 -101.8(7) . . . . ? Tl4 O1 C17 C18 137.5(6) . . . . ? Tl2 O1 C17 C23 -162.2(6) . . . . ? Tl1 O1 C17 C23 76.6(8) . . . . ? Tl4 O1 C17 C23 -44.1(8) . . . . ? O1 C17 C18 C14 176.5(7) . . . . ? C23 C17 C18 C14 -1.9(11) . . . . ? C13 C14 C18 C17 0.2(12) . . . . ? O4 C5 C19 C9 -173.8(8) . . . . ? C6 C5 C19 C9 6.6(14) . . . . ? C8 C9 C19 C5 -1.6(14) . . . . ? C2 C1 C20 C21 1.6(17) . . . . ? O3 C1 C20 C21 179.3(10) . . . . ? C3 C4 C21 C20 1.6(18) . . . . ? I6 C4 C21 C20 -177.2(9) . . . . ? C1 C20 C21 C4 -2.6(19) . . . . ? C11 C12 C22 C15 3.6(14) . . . . ? C25 C15 C22 C12 -1.4(13) . . . . ? I8 C15 C22 C12 178.7(6) . . . . ? O1 C17 C23 C24 -177.7(7) . . . . ? C18 C17 C23 C24 0.8(12) . . . . ? C14 C13 C24 C23 -4.0(13) . . . . ? I5 C13 C24 C23 175.3(6) . . . . ? C17 C23 C24 C13 2.2(13) . . . . ? C11 C10 C25 C15 1.5(14) . . . . ? C22 C15 C25 C10 -1.1(13) . . . . ? I8 C15 C25 C10 178.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.627 _refine_diff_density_min -1.417 _refine_diff_density_rms 0.209 data_5 _database_code_depnum_ccdc_archive 'CCDC 824705' #TrackingRef '- 1-9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H12 Br4 Cl4 O4 Tl4' _chemical_formula_sum 'C24 H12 Br4 Cl4 O4 Tl4' _chemical_formula_weight 1643.26 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I41/a _symmetry_space_group_name_Hall '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+3/4, x+1/4, z+1/4' '-x+1/2, -y, z+1/2' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-y+5/4, x+3/4, z+3/4' '-x+1, -y+1/2, z+1' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'y-3/4, -x-1/4, -z-1/4' 'x-1/2, y, -z-1/2' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' 'x, y+1/2, -z' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 17.4773(7) _cell_length_b 17.4773(7) _cell_length_c 10.2912(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3143.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2146 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 29.30 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.039 _exptl_crystal_size_mid 0.115 _exptl_crystal_size_max 0.119 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2880.0 _exptl_absorpt_coefficient_mu 25.898 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4890 _exptl_absorpt_correction_T_max 0.6955 _exptl_absorpt_process_details 'SADABS V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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_reflns_number 10274 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 32.84 _reflns_number_total 2925 _reflns_number_gt 2069 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0590P)^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 2659 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.0778 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 Tl1 Tl 0.124010(17) 0.263927(18) 0.73876(3) 0.01547(11) Uani 1 1 d . . . Br1 Br 0.19407(5) 0.39847(5) 0.53652(7) 0.0211(2) Uani 1 1 d . . . Cl1 Cl 0.24002(13) 0.34790(13) 0.01361(18) 0.0221(4) Uani 1 1 d . . . O1 O 0.0867(3) 0.2590(3) 0.5012(5) 0.0133(10) Uani 1 1 d . . . C1 C 0.1228(4) 0.2782(5) 0.3924(7) 0.0151(15) Uani 1 1 d . . . C2 C 0.1729(5) 0.3407(4) 0.3841(7) 0.0144(15) Uani 1 1 d . . . C3 C 0.2097(5) 0.3616(5) 0.2697(7) 0.0159(15) Uani 1 1 d . . . H3 H 0.2435 0.4027 0.2685 0.019 Uiso 1 1 calc R . . C4 C 0.1956(4) 0.3206(4) 0.1584(7) 0.0143(15) Uani 1 1 d . . . C5 C 0.1469(5) 0.2584(4) 0.1598(7) 0.0165(16) Uani 1 1 d . . . H5 H 0.1382 0.2308 0.0839 0.020 Uiso 1 1 calc R . . C6 C 0.1107(5) 0.2370(5) 0.2745(7) 0.0160(15) Uani 1 1 d . . . H6 H 0.0780 0.1951 0.2744 0.019 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 Tl1 0.01505(17) 0.01866(18) 0.01271(14) 0.00004(10) -0.00140(9) -0.00048(11) Br1 0.0234(5) 0.0239(5) 0.0161(3) -0.0047(3) 0.0027(3) -0.0098(3) Cl1 0.0228(11) 0.0281(12) 0.0153(7) 0.0057(7) 0.0066(7) 0.0026(9) O1 0.013(3) 0.016(3) 0.010(2) 0.0014(18) 0.0011(19) 0.000(2) C1 0.011(4) 0.019(4) 0.015(3) 0.002(3) 0.002(3) 0.006(3) C2 0.019(4) 0.011(4) 0.013(3) 0.001(3) -0.001(3) -0.003(3) C3 0.012(4) 0.018(4) 0.017(3) 0.000(3) 0.002(3) 0.000(3) C4 0.014(4) 0.017(4) 0.012(3) 0.004(3) 0.005(3) 0.006(3) C5 0.018(4) 0.018(4) 0.013(3) 0.003(3) -0.001(3) 0.002(3) C6 0.018(4) 0.015(4) 0.015(3) 0.000(3) -0.002(3) -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 Tl1 O1 2.532(5) . ? Tl1 O1 2.651(6) 12_667 ? Tl1 O1 2.673(6) 14_556 ? Br1 C2 1.902(7) . ? Cl1 C4 1.747(7) . ? O1 C1 1.328(9) . ? O1 Tl1 2.651(6) 14_556 ? O1 Tl1 2.673(6) 12_667 ? C1 C2 1.402(11) . ? C1 C6 1.427(11) . ? C2 C3 1.391(10) . ? C3 C4 1.373(10) . ? C3 H3 0.9300 . ? C4 C5 1.381(11) . ? C5 C6 1.390(10) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Tl1 O1 80.10(19) . 12_667 ? O1 Tl1 O1 79.69(19) . 14_556 ? O1 Tl1 O1 69.8(2) 12_667 14_556 ? C1 O1 Tl1 133.1(5) . . ? C1 O1 Tl1 118.9(5) . 14_556 ? Tl1 O1 Tl1 96.65(16) . 14_556 ? C1 O1 Tl1 98.9(4) . 12_667 ? Tl1 O1 Tl1 96.12(17) . 12_667 ? Tl1 O1 Tl1 110.0(2) 14_556 12_667 ? O1 C1 C2 123.1(7) . . ? O1 C1 C6 121.3(8) . . ? C2 C1 C6 115.7(7) . . ? C3 C2 C1 123.1(7) . . ? C3 C2 Br1 118.0(6) . . ? C1 C2 Br1 119.0(5) . . ? C4 C3 C2 119.0(8) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 120.9(7) . . ? C3 C4 Cl1 119.2(6) . . ? C5 C4 Cl1 119.9(6) . . ? C4 C5 C6 120.0(7) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 121.3(8) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Tl1 O1 C1 128.2(7) 12_667 . . . ? O1 Tl1 O1 C1 -160.7(7) 14_556 . . . ? O1 Tl1 O1 Tl1 -91.08(5) 12_667 . . 14_556 ? O1 Tl1 O1 Tl1 -20.0(2) 14_556 . . 14_556 ? O1 Tl1 O1 Tl1 20.0(2) 12_667 . . 12_667 ? O1 Tl1 O1 Tl1 91.03(5) 14_556 . . 12_667 ? Tl1 O1 C1 C2 -35.1(11) . . . . ? Tl1 O1 C1 C2 -169.2(6) 14_556 . . . ? Tl1 O1 C1 C2 72.0(7) 12_667 . . . ? Tl1 O1 C1 C6 146.7(6) . . . . ? Tl1 O1 C1 C6 12.6(9) 14_556 . . . ? Tl1 O1 C1 C6 -106.2(7) 12_667 . . . ? O1 C1 C2 C3 -178.9(7) . . . . ? C6 C1 C2 C3 -0.7(11) . . . . ? O1 C1 C2 Br1 2.7(10) . . . . ? C6 C1 C2 Br1 -179.0(6) . . . . ? C1 C2 C3 C4 1.4(12) . . . . ? Br1 C2 C3 C4 179.8(6) . . . . ? C2 C3 C4 C5 -1.4(12) . . . . ? C2 C3 C4 Cl1 178.5(6) . . . . ? C3 C4 C5 C6 0.7(12) . . . . ? Cl1 C4 C5 C6 -179.2(6) . . . . ? C4 C5 C6 C1 0.0(12) . . . . ? O1 C1 C6 C5 178.3(7) . . . . ? C2 C1 C6 C5 0.0(11) . . . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.651 _refine_diff_density_min -2.352 _refine_diff_density_rms 0.664 data_6 _database_code_depnum_ccdc_archive 'CCDC 824706' #TrackingRef '- 1-9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H12 Cl4 F4 O4 Tl4' _chemical_formula_sum 'C24 H12 Cl4 F4 O4 Tl4' _chemical_formula_weight 1399.62 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 15.1961(4) _cell_length_b 15.0703(4) _cell_length_c 26.0915(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5975.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9704 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.40 _exptl_crystal_description IRREGULAR _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.112 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4928 _exptl_absorpt_coefficient_mu 21.921 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2693 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 211401 _diffrn_reflns_av_R_equivalents 0.0766 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6847 _reflns_number_gt 5192 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0327P)^2^+24.8831P] 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 6847 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0722 _refine_ls_wR_factor_gt 0.0616 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.002 _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 Tl1 Tl 0.735614(19) 1.001086(16) 0.871496(10) 0.04701(8) Uani 1 1 d . . . Tl2 Tl 0.54939(2) 0.860163(19) 0.948170(11) 0.05326(9) Uani 1 1 d . . . Tl3 Tl 0.77743(2) 0.750652(18) 0.891129(12) 0.05626(9) Uani 1 1 d . . . Tl4 Tl 0.56795(2) 0.829316(19) 0.802567(11) 0.05507(9) Uani 1 1 d . . . Cl1 Cl 0.71952(16) 0.67859(12) 0.76958(9) 0.0720(6) Uani 1 1 d . . . Cl2 Cl 0.63873(17) 0.67695(14) 0.99385(8) 0.0727(6) Uani 1 1 d . . . Cl3 Cl 0.65031(14) 1.05427(13) 0.98677(8) 0.0656(5) Uani 1 1 d . . . Cl4 Cl 0.59748(17) 1.03479(16) 0.76229(8) 0.0750(6) Uani 1 1 d . . . F1 F 0.8775(4) 0.8333(4) 0.62550(18) 0.0947(18) Uani 1 1 d . . . F2 F 0.5337(4) 0.3878(3) 0.9200(3) 0.109(2) Uani 1 1 d . . . F3 F 0.8275(4) 0.9582(5) 1.13883(19) 0.114(2) Uani 1 1 d . . . F4 F 0.4251(7) 1.2869(5) 0.8368(3) 0.165(4) Uani 1 1 d . . . O3 O 0.7199(3) 0.8862(3) 0.94336(17) 0.0504(12) Uani 1 1 d . . . C5 C 0.8048(5) 0.7643(5) 0.6950(3) 0.060(2) Uani 1 1 d . . . H5 H 0.8021 0.7113 0.6768 0.072 Uiso 1 1 calc R . . C9 C 0.5784(5) 0.5258(5) 0.9523(3) 0.062(2) Uani 1 1 d . . . H9 H 0.5863 0.5008 0.9845 0.075 Uiso 1 1 calc R . . C23 C 0.4433(8) 1.1614(7) 0.8892(4) 0.096(4) Uani 1 1 d . . . H23 H 0.4095 1.1880 0.9146 0.115 Uiso 1 1 calc R . . O4 O 0.5667(3) 0.9571(3) 0.86592(17) 0.0488(11) Uani 1 1 d . . . O2 O 0.6034(4) 0.7398(3) 0.88720(19) 0.0545(12) Uani 1 1 d . . . O1 O 0.7369(4) 0.8553(3) 0.81841(18) 0.0556(13) Uani 1 1 d . . . C1 C 0.7741(5) 0.8495(4) 0.7721(3) 0.0456(15) Uani 1 1 d . . . C6 C 0.7715(5) 0.7713(4) 0.7436(3) 0.0496(17) Uani 1 1 d . . . C4 C 0.8425(5) 0.8392(6) 0.6744(3) 0.063(2) Uani 1 1 d . . . C3 C 0.8480(5) 0.9178(6) 0.6994(3) 0.066(2) Uani 1 1 d . . . H3 H 0.8737 0.9671 0.6841 0.079 Uiso 1 1 calc R . . C2 C 0.8143(5) 0.9223(5) 0.7483(3) 0.0556(18) Uani 1 1 d . . . H2 H 0.8184 0.9756 0.7662 0.067 Uiso 1 1 calc R . . C7 C 0.5836(5) 0.6557(4) 0.8956(3) 0.0471(16) Uani 1 1 d . . . C12 C 0.5501(5) 0.6006(5) 0.8567(3) 0.0575(18) Uani 1 1 d . . . H12 H 0.5387 0.6247 0.8246 0.069 Uiso 1 1 calc R . . C11 C 0.5335(6) 0.5107(6) 0.8650(4) 0.071(2) Uani 1 1 d . . . H11 H 0.5124 0.4748 0.8387 0.085 Uiso 1 1 calc R . . C10 C 0.5489(6) 0.4769(5) 0.9125(4) 0.072(2) Uani 1 1 d . . . C8 C 0.5963(5) 0.6148(5) 0.9433(3) 0.0566(18) Uani 1 1 d . . . C13 C 0.7474(5) 0.9035(5) 0.9905(3) 0.0487(16) Uani 1 1 d . . . C14 C 0.8052(6) 0.8475(6) 1.0177(3) 0.063(2) Uani 1 1 d . . . H14 H 0.8258 0.7962 1.0021 0.076 Uiso 1 1 calc R . . C15 C 0.8318(6) 0.8667(7) 1.0668(3) 0.078(3) Uani 1 1 d . . . H15 H 0.8702 0.8287 1.0837 0.093 Uiso 1 1 calc R . . C16 C 0.8027(6) 0.9397(7) 1.0902(3) 0.071(2) Uani 1 1 d . . . C17 C 0.7477(6) 0.9990(6) 1.0664(3) 0.068(2) Uani 1 1 d . . . H17 H 0.7292 1.0506 1.0829 0.082 Uiso 1 1 calc R . . C18 C 0.7203(4) 0.9791(5) 1.0167(3) 0.0495(16) Uani 1 1 d . . . C19 C 0.5304(5) 1.0366(5) 0.8587(3) 0.0470(16) Uani 1 1 d . . . C20 C 0.5411(5) 1.0839(5) 0.8129(3) 0.0591(19) Uani 1 1 d . . . C21 C 0.5071(7) 1.1676(6) 0.8057(4) 0.085(3) Uani 1 1 d . . . H21 H 0.5166 1.1979 0.7752 0.102 Uiso 1 1 calc R . . C22 C 0.4598(8) 1.2050(7) 0.8437(5) 0.099(4) Uani 1 1 d . . . C24 C 0.4783(6) 1.0772(6) 0.8964(3) 0.065(2) Uani 1 1 d . . . H24 H 0.4669 1.0471 0.9268 0.078 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 Tl1 0.05485(17) 0.03988(14) 0.04629(15) -0.00170(10) -0.00302(12) -0.00186(11) Tl2 0.05618(18) 0.05733(17) 0.04625(15) -0.00179(12) 0.00605(12) 0.00549(13) Tl3 0.0671(2) 0.04515(15) 0.05648(18) 0.00130(12) 0.00357(14) 0.00790(13) Tl4 0.06425(19) 0.05277(16) 0.04819(16) -0.01037(12) -0.00445(13) -0.00072(13) Cl1 0.1033(17) 0.0389(9) 0.0737(13) -0.0007(9) 0.0260(12) -0.0016(10) Cl2 0.1009(17) 0.0678(13) 0.0494(11) 0.0021(9) -0.0013(11) 0.0155(11) Cl3 0.0703(13) 0.0649(12) 0.0616(12) -0.0078(9) -0.0043(10) 0.0167(10) Cl4 0.0928(16) 0.0814(14) 0.0510(11) 0.0093(10) 0.0024(11) -0.0001(12) F1 0.109(5) 0.115(4) 0.060(3) -0.002(3) 0.038(3) -0.018(4) F2 0.118(5) 0.061(3) 0.148(5) 0.027(3) -0.010(4) -0.034(3) F3 0.099(4) 0.201(7) 0.043(3) -0.010(3) -0.016(3) 0.003(5) F4 0.254(10) 0.089(5) 0.151(6) -0.017(4) -0.075(6) 0.102(6) O3 0.062(3) 0.046(3) 0.044(3) 0.001(2) -0.007(2) 0.005(2) C5 0.066(5) 0.060(5) 0.054(5) -0.014(4) 0.006(4) 0.004(4) C9 0.054(5) 0.058(5) 0.075(6) 0.020(4) 0.015(4) 0.006(4) C23 0.115(9) 0.084(7) 0.089(7) -0.026(6) -0.020(6) 0.056(6) O4 0.056(3) 0.046(3) 0.044(3) -0.001(2) 0.000(2) 0.003(2) O2 0.068(3) 0.046(3) 0.049(3) 0.001(2) 0.005(2) 0.001(2) O1 0.075(4) 0.045(3) 0.047(3) -0.003(2) 0.014(3) 0.004(2) C1 0.050(4) 0.044(4) 0.043(4) 0.003(3) 0.005(3) 0.004(3) C6 0.055(4) 0.042(4) 0.051(4) 0.005(3) 0.011(3) 0.004(3) C4 0.060(5) 0.083(6) 0.047(4) -0.002(4) 0.012(4) -0.004(4) C3 0.054(5) 0.076(6) 0.066(5) 0.014(4) 0.013(4) -0.011(4) C2 0.056(5) 0.048(4) 0.063(5) -0.005(3) 0.008(4) -0.006(3) C7 0.046(4) 0.041(4) 0.054(4) 0.001(3) 0.006(3) 0.003(3) C12 0.048(4) 0.059(4) 0.065(5) -0.002(4) 0.000(4) -0.004(3) C11 0.055(5) 0.064(5) 0.095(7) -0.010(5) -0.004(5) -0.016(4) C10 0.060(5) 0.046(4) 0.110(8) 0.015(5) 0.003(5) -0.011(4) C8 0.054(5) 0.062(5) 0.054(4) -0.001(4) 0.008(4) 0.008(4) C13 0.045(4) 0.060(4) 0.041(4) 0.004(3) -0.002(3) -0.002(3) C14 0.066(5) 0.075(5) 0.048(4) 0.014(4) -0.004(4) 0.005(4) C15 0.067(6) 0.115(8) 0.050(5) 0.018(5) -0.003(4) 0.011(5) C16 0.058(5) 0.120(8) 0.035(4) 0.005(5) -0.008(4) -0.011(5) C17 0.067(5) 0.093(7) 0.044(4) -0.007(4) 0.005(4) -0.009(5) C18 0.045(4) 0.062(4) 0.041(4) 0.004(3) 0.003(3) -0.002(3) C19 0.046(4) 0.046(4) 0.049(4) -0.005(3) -0.014(3) 0.001(3) C20 0.066(5) 0.052(4) 0.059(5) 0.003(3) -0.019(4) 0.000(4) C21 0.115(9) 0.067(6) 0.074(6) 0.015(5) -0.036(6) 0.014(6) C22 0.128(10) 0.071(6) 0.096(8) -0.007(6) -0.050(7) 0.043(6) C24 0.070(5) 0.070(5) 0.054(5) -0.009(4) -0.009(4) 0.018(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Tl1 O3 2.563(5) . ? Tl1 O1 2.597(5) . ? Tl1 O4 2.655(5) . ? Tl2 O2 2.548(5) . ? Tl2 O4 2.609(5) . ? Tl2 O3 2.623(5) . ? Tl3 O1 2.543(5) . ? Tl3 O3 2.607(5) . ? Tl3 O2 2.651(6) . ? Tl4 O4 2.538(4) . ? Tl4 O1 2.630(6) . ? Tl4 O2 2.643(5) . ? Cl1 C6 1.743(7) . ? Cl2 C8 1.740(8) . ? Cl3 C18 1.739(7) . ? Cl4 C20 1.740(9) . ? F1 C4 1.384(8) . ? F2 C10 1.376(9) . ? F3 C16 1.353(9) . ? F4 C22 1.354(11) . ? O3 C13 1.326(8) . ? C5 C6 1.369(10) . ? C5 C4 1.376(11) . ? C9 C10 1.350(13) . ? C9 C8 1.388(11) . ? C23 C22 1.380(16) . ? C23 C24 1.388(12) . ? O4 C19 1.332(8) . ? O2 C7 1.321(8) . ? O1 C1 1.338(8) . ? C1 C6 1.393(10) . ? C1 C2 1.401(10) . ? C4 C3 1.355(12) . ? C3 C2 1.376(11) . ? C7 C8 1.404(10) . ? C7 C12 1.406(10) . ? C12 C11 1.395(11) . ? C11 C10 1.361(13) . ? C13 C18 1.391(10) . ? C13 C14 1.410(10) . ? C14 C15 1.372(12) . ? C15 C16 1.334(13) . ? C16 C17 1.372(12) . ? C17 C18 1.395(11) . ? C19 C20 1.399(10) . ? C19 C24 1.405(10) . ? C20 C21 1.377(12) . ? C21 C22 1.347(15) . ? 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 O3 Tl1 O1 79.60(14) . . ? O3 Tl1 O4 77.36(15) . . ? O1 Tl1 O4 76.52(16) . . ? O2 Tl2 O4 81.53(14) . . ? O2 Tl2 O3 76.03(16) . . ? O4 Tl2 O3 77.13(14) . . ? O1 Tl3 O3 79.79(14) . . ? O1 Tl3 O2 76.57(16) . . ? O3 Tl3 O2 74.56(15) . . ? O4 Tl4 O1 78.00(15) . . ? O4 Tl4 O2 81.06(14) . . ? O1 Tl4 O2 75.26(16) . . ? C13 O3 Tl1 121.1(4) . . ? C13 O3 Tl3 122.2(4) . . ? Tl1 O3 Tl3 96.64(15) . . ? C13 O3 Tl2 107.2(4) . . ? Tl1 O3 Tl2 103.21(16) . . ? Tl3 O3 Tl2 103.83(16) . . ? C6 C5 C4 116.9(7) . . ? C10 C9 C8 117.7(8) . . ? C22 C23 C24 118.8(9) . . ? C19 O4 Tl4 126.4(4) . . ? C19 O4 Tl2 125.4(4) . . ? Tl4 O4 Tl2 96.40(15) . . ? C19 O4 Tl1 100.6(4) . . ? Tl4 O4 Tl1 102.58(16) . . ? Tl2 O4 Tl1 101.07(15) . . ? C7 O2 Tl2 120.4(4) . . ? C7 O2 Tl4 125.5(4) . . ? Tl2 O2 Tl4 95.32(15) . . ? C7 O2 Tl3 106.2(4) . . ? Tl2 O2 Tl3 104.68(18) . . ? Tl4 O2 Tl3 101.79(17) . . ? C1 O1 Tl3 122.1(4) . . ? C1 O1 Tl1 122.7(4) . . ? Tl3 O1 Tl1 97.38(16) . . ? C1 O1 Tl4 105.1(4) . . ? Tl3 O1 Tl4 105.16(18) . . ? Tl1 O1 Tl4 101.68(17) . . ? O1 C1 C6 121.7(6) . . ? O1 C1 C2 122.2(6) . . ? C6 C1 C2 116.0(6) . . ? C5 C6 C1 123.3(7) . . ? C5 C6 Cl1 117.8(6) . . ? C1 C6 Cl1 118.9(5) . . ? C3 C4 C5 123.6(7) . . ? C3 C4 F1 118.5(7) . . ? C5 C4 F1 117.8(7) . . ? C4 C3 C2 117.9(7) . . ? C3 C2 C1 122.2(7) . . ? O2 C7 C8 122.4(7) . . ? O2 C7 C12 122.0(7) . . ? C8 C7 C12 115.5(7) . . ? C11 C12 C7 121.9(8) . . ? C10 C11 C12 118.2(8) . . ? C9 C10 C11 123.6(8) . . ? C9 C10 F2 118.6(9) . . ? C11 C10 F2 117.8(9) . . ? C9 C8 C7 123.0(8) . . ? C9 C8 Cl2 117.8(6) . . ? C7 C8 Cl2 119.2(6) . . ? O3 C13 C18 121.6(6) . . ? O3 C13 C14 123.1(7) . . ? C18 C13 C14 115.3(7) . . ? C15 C14 C13 121.8(8) . . ? C16 C15 C14 120.2(9) . . ? C15 C16 F3 120.5(9) . . ? C15 C16 C17 122.2(8) . . ? F3 C16 C17 117.3(9) . . ? C16 C17 C18 117.5(8) . . ? C13 C18 C17 123.0(7) . . ? C13 C18 Cl3 119.6(5) . . ? C17 C18 Cl3 117.4(6) . . ? O4 C19 C20 122.1(7) . . ? O4 C19 C24 121.7(7) . . ? C20 C19 C24 116.2(7) . . ? C21 C20 C19 122.7(8) . . ? C21 C20 Cl4 118.1(7) . . ? C19 C20 Cl4 119.2(6) . . ? C22 C21 C20 118.9(9) . . ? C21 C22 F4 119.4(11) . . ? C21 C22 C23 122.0(9) . . ? F4 C22 C23 118.5(11) . . ? C23 C24 C19 121.3(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.401 _refine_diff_density_min -1.415 _refine_diff_density_rms 0.139