# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Pilar Gonzalez-Duarte' _publ_contact_author_email PILAR.GONZALEZ.DUARTE@UAB.ES _publ_section_title ; Crystal structure of thioflavin-T and its binding to amyloid fibrils: insights and implications at the molecular level ; loop_ _publ_author_name 'Pilar Gonzalez-Duarte' 'A Alvarez-Larena' 'Hugo Gutierrez-de-Teran' ; A.Rimola ; 'Cristina Rodriguez-Rodriguez' 'Luis Rodriguez-Santiago' 'Mariona Sodupe' 'Piero Ugliengo' # Attachment 'cr06_0403091.cif' data_C1 _database_code_depnum_ccdc_archive 'CCDC 728298' _audit_creation_method SHELXL-97 _chemical_formula_moiety '(C17 H19 N2 S 1+)2, I4 2-, 2(C H Cl3)' _chemical_formula_sum 'C36 H40 Cl6 I4 N4 S2' _chemical_formula_weight 1313.14 _chemical_name_systematic ; bis[2-(4-(dimethylamino)phenyl)-3,6-dimethylbenzo[d]thiazol-3-ium] tetraiodide, chloroform solvate 1:2 ; 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _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_angle_alpha 90.00 _cell_angle_beta 112.525(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 36.297(3) _cell_length_b 7.1666(5) _cell_length_c 19.5063(13) _cell_measurement_reflns_used 1921 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 21.42 _cell_measurement_theta_min 2.90 _cell_volume 4687.0(6) _exptl_absorpt_coefficient_mu 3.121 _exptl_absorpt_correction_T_max 0.911 _exptl_absorpt_correction_T_min 0.515 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, 2.05' _exptl_crystal_F_000 2520 _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.861 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 8.13 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.917 _diffrn_measurement_device_type 'Bruker SMART-APEX diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 15766 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.10 _diffrn_reflns_theta_min 1.21 _diffrn_standards_decay_% 1.3 _diffrn_standards_number 203 _reflns_number_gt 3500 _reflns_number_total 5775 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT 5.0 (Bruker)' _computing_data_collection 'SMART 5.6 (Bruker)' _computing_data_reduction 'SAINT 5.0 (Bruker)' _computing_molecular_graphics ; Olex2, Durham University (compiled Feb 15 2009 13:03:59) ; _computing_publication_material ; Olex2, Durham University (compiled Feb 15 2009 13:03:59) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.898 _refine_diff_density_min -0.672 _refine_diff_density_rms 0.203 _refine_ls_R_factor_all 0.0968 _refine_ls_R_factor_gt 0.0524 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 223 _refine_ls_number_reflns 5775 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1233 _refine_ls_wR_factor_ref 0.1431 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0669P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C1 C 0.3284(2) 0.2392(7) 0.7094(4) 0.0560(15) Uani 1 1 d . . . C2 C 0.2935(2) 0.1991(8) 0.6456(4) 0.0638(16) Uani 1 1 d . . . H2 H 0.2960 0.1671 0.6014 0.077 Uiso 1 1 calc R . . C3 C 0.25682(19) 0.2067(8) 0.6478(3) 0.0560(14) Uani 1 1 d . . . H3 H 0.2348 0.1832 0.6045 0.067 Uiso 1 1 calc R . . C4 C 0.25050(18) 0.2486(7) 0.7132(3) 0.0484(13) Uani 1 1 d . . . C5 C 0.28519(17) 0.2743(7) 0.7777(3) 0.0483(13) Uani 1 1 d . . . H5 H 0.2827 0.2957 0.8227 0.058 Uiso 1 1 calc R . . C6 C 0.32216(19) 0.2688(7) 0.7759(3) 0.0562(15) Uani 1 1 d . . . H6 H 0.3442 0.2850 0.8199 0.067 Uiso 1 1 calc R . . N11 N 0.36452(19) 0.2423(7) 0.7064(4) 0.0776(16) Uani 1 1 d . . . C12 C 0.4004(2) 0.2779(10) 0.7725(5) 0.092(3) Uani 1 1 d . . . H12A H 0.3974 0.3933 0.7949 0.139 Uiso 1 1 calc R . . H12B H 0.4230 0.2861 0.7587 0.139 Uiso 1 1 calc R . . H12C H 0.4043 0.1779 0.8073 0.139 Uiso 1 1 calc R . . C13 C 0.3700(3) 0.2172(12) 0.6368(5) 0.103(3) Uani 1 1 d . . . H13A H 0.3647 0.0897 0.6210 0.155 Uiso 1 1 calc R . . H13B H 0.3970 0.2477 0.6439 0.155 Uiso 1 1 calc R . . H13C H 0.3521 0.2975 0.5996 0.155 Uiso 1 1 calc R . . N21 N 0.17698(14) 0.2968(6) 0.6624(2) 0.0496(11) Uani 1 1 d . . . C22 C 0.21201(17) 0.2574(6) 0.7172(3) 0.0460(13) Uani 1 1 d . . . S23 S 0.20638(4) 0.2152(2) 0.79997(7) 0.0496(3) Uani 1 1 d . . . C24 C 0.15547(17) 0.2501(7) 0.7586(3) 0.0480(13) Uani 1 1 d . . . C25 C 0.14440(17) 0.2889(7) 0.6838(3) 0.0503(13) Uani 1 1 d . . . C26 C 0.10480(19) 0.3162(8) 0.6382(4) 0.0636(16) Uani 1 1 d . . . H26 H 0.0972 0.3389 0.5877 0.076 Uiso 1 1 calc R . . C27 C 0.0772(2) 0.3082(9) 0.6705(4) 0.0707(18) Uani 1 1 d . . . H27 H 0.0504 0.3266 0.6408 0.085 Uiso 1 1 calc R . . C28 C 0.08771(19) 0.2736(8) 0.7463(4) 0.0627(16) Uani 1 1 d . . . C29 C 0.12724(19) 0.2431(7) 0.7913(3) 0.0565(15) Uani 1 1 d . . . H29 H 0.1348 0.2186 0.8417 0.068 Uiso 1 1 calc R . . C31 C 0.1720(2) 0.3685(9) 0.5886(3) 0.0682(17) Uani 1 1 d . . . H31A H 0.1970 0.4159 0.5901 0.102 Uiso 1 1 calc R . . H31B H 0.1525 0.4668 0.5748 0.102 Uiso 1 1 calc R . . H31C H 0.1631 0.2694 0.5529 0.102 Uiso 1 1 calc R . . C32 C 0.0558(2) 0.2721(11) 0.7789(4) 0.090(2) Uani 1 1 d . . . H32A H 0.0314 0.2239 0.7428 0.135 Uiso 1 1 calc R . . H32B H 0.0515 0.3970 0.7921 0.135 Uiso 1 1 calc R . . H32C H 0.0643 0.1946 0.8223 0.135 Uiso 1 1 calc R . . I1 I 0.120974(15) 0.86928(7) 0.50587(2) 0.07597(19) Uani 1 1 d . . . I2 I 0.211468(13) 0.78667(6) 0.499619(19) 0.06554(17) Uani 1 1 d . . . C10 C 0.02973(6) 0.2270(3) 0.42719(12) 0.059(4) Uiso 0.37 1 d PG A 1 H10 H 0.0473 0.1276 0.4563 0.089 Uiso 0.37 1 d PG A 1 Cl11 Cl 0.05657(9) 0.4394(4) 0.44238(15) 0.0717(13) Uiso 0.37 1 d PG A 1 Cl12 Cl -0.01112(9) 0.2520(4) 0.45483(16) 0.104(2) Uiso 0.37 1 d PG A 1 Cl13 Cl 0.01191(9) 0.1693(7) 0.33175(15) 0.0935(16) Uiso 0.37 1 d PG A 1 C20 C 0.02262(7) 0.1897(3) 0.44048(14) 0.051(3) Uiso 0.38 1 d PG A 2 H20 H 0.0426 0.1173 0.4800 0.076 Uiso 0.38 1 d PG A 2 Cl21 Cl 0.00990(9) 0.0708(6) 0.3550(2) 0.0953(16) Uiso 0.38 1 d PG A 2 Cl22 Cl 0.04239(9) 0.4119(3) 0.43418(13) 0.0878(18) Uiso 0.38 1 d PG A 2 Cl23 Cl -0.02055(9) 0.2173(4) 0.46098(19) 0.0933(18) Uiso 0.38 1 d PG A 2 C30 C -0.00156(8) 0.3558(4) 0.38138(12) 0.060 Uiso 0.13 1 d PG A 3 H30 H -0.0212 0.4535 0.3574 0.090 Uiso 0.13 1 d PG A 3 Cl31 Cl 0.01068(10) 0.2363(8) 0.31354(12) 0.057(3) Uiso 0.13 1 d PG . 3 Cl32 Cl -0.02191(7) 0.1965(4) 0.42674(18) 0.099(5) Uiso 0.13 1 d PG A 3 Cl33 Cl 0.04202(10) 0.4583(3) 0.44721(15) 0.111(8) Uiso 0.13 1 d PG A 3 C40 C 0.00228(6) 0.2366(4) 0.40038(13) 0.060 Uiso 0.12 1 d PG A 4 H40 H -0.0201 0.3006 0.3624 0.090 Uiso 0.12 1 d PG A 4 Cl41 Cl 0.00397(9) 0.0019(5) 0.3734(3) 0.087(5) Uiso 0.12 1 d PG A 4 Cl42 Cl -0.00402(10) 0.2424(4) 0.48595(16) 0.089(5) Uiso 0.12 1 d PG A 4 Cl43 Cl 0.04741(8) 0.3498(4) 0.41047(12) 0.158(10) Uiso 0.12 1 d PG A 4 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 C1 0.067(4) 0.036(3) 0.077(4) 0.007(3) 0.041(3) 0.004(3) C2 0.081(5) 0.056(4) 0.066(4) -0.005(3) 0.041(4) -0.001(3) C3 0.069(4) 0.051(3) 0.049(3) -0.004(3) 0.023(3) -0.003(3) C4 0.063(4) 0.035(3) 0.047(3) -0.001(2) 0.021(3) -0.003(2) C5 0.056(4) 0.044(3) 0.048(3) 0.003(2) 0.023(3) -0.001(3) C6 0.064(4) 0.041(3) 0.058(3) 0.009(3) 0.018(3) 0.001(3) N11 0.078(4) 0.060(4) 0.107(5) 0.007(3) 0.049(4) 0.001(3) C12 0.072(5) 0.073(5) 0.142(8) 0.015(5) 0.052(5) 0.007(4) C13 0.117(7) 0.102(6) 0.125(7) 0.023(5) 0.086(6) 0.019(5) N21 0.062(3) 0.041(2) 0.046(2) 0.0012(19) 0.020(2) 0.000(2) C22 0.062(4) 0.031(3) 0.044(3) -0.001(2) 0.020(3) -0.003(2) S23 0.0547(9) 0.0519(8) 0.0417(7) -0.0015(6) 0.0177(6) -0.0029(7) C24 0.053(3) 0.037(3) 0.051(3) -0.006(2) 0.017(3) -0.009(2) C25 0.055(4) 0.038(3) 0.055(3) -0.006(2) 0.017(3) -0.003(3) C26 0.058(4) 0.058(4) 0.067(4) -0.004(3) 0.016(3) -0.003(3) C27 0.053(4) 0.064(4) 0.080(5) -0.007(3) 0.009(3) -0.003(3) C28 0.059(4) 0.056(4) 0.073(4) -0.009(3) 0.026(3) -0.003(3) C29 0.070(4) 0.048(3) 0.052(3) -0.012(2) 0.023(3) -0.015(3) C31 0.079(5) 0.072(4) 0.052(3) 0.022(3) 0.024(3) 0.005(3) C32 0.075(5) 0.098(6) 0.109(6) -0.008(5) 0.048(5) -0.011(4) I1 0.0825(4) 0.0733(3) 0.0720(3) 0.0111(2) 0.0295(3) 0.0111(2) I2 0.0783(3) 0.0693(3) 0.0444(2) -0.00176(18) 0.0183(2) -0.0130(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 C1 N11 1.335(8) . ? C1 C6 1.414(8) . ? C1 C2 1.424(9) . ? C2 C3 1.349(9) . ? C3 C4 1.413(8) . ? C4 C5 1.409(8) . ? C4 C22 1.430(8) . ? C5 C6 1.357(8) . ? N11 C13 1.459(10) . ? N11 C12 1.461(9) . ? N21 C22 1.341(7) . ? N21 C25 1.398(7) . ? N21 C31 1.472(7) . ? C22 S23 1.730(5) . ? S23 C24 1.728(6) . ? C24 C25 1.386(8) . ? C24 C29 1.399(8) . ? C25 C26 1.384(8) . ? C26 C27 1.375(9) . ? C27 C28 1.401(9) . ? C28 C29 1.382(9) . ? C28 C32 1.519(9) . ? I2 I2 2.8406(10) 7_566 ? C10 Cl11 1.7699 . ? C10 Cl12 1.7700 . ? C10 Cl13 1.7700 . ? C20 Cl22 1.7699 . ? C20 Cl21 1.7700 . ? C20 Cl23 1.7701 . ? C30 Cl31 1.7699 . ? C30 Cl32 1.7700 . ? C30 Cl33 1.7701 . ? Cl31 Cl31 2.296(4) 2 ? C40 Cl41 1.7699 . ? C40 Cl42 1.7700 . ? C40 Cl43 1.7700 . ? 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 N11 C1 C6 122.8(6) . . ? N11 C1 C2 121.7(6) . . ? C6 C1 C2 115.5(6) . . ? C3 C2 C1 121.4(6) . . ? C2 C3 C4 122.8(6) . . ? C5 C4 C3 115.8(6) . . ? C5 C4 C22 120.2(5) . . ? C3 C4 C22 123.9(5) . . ? C6 C5 C4 121.8(5) . . ? C5 C6 C1 122.3(6) . . ? C1 N11 C13 121.7(7) . . ? C1 N11 C12 121.5(6) . . ? C13 N11 C12 116.7(7) . . ? C22 N21 C25 113.9(5) . . ? C22 N21 C31 125.2(5) . . ? C25 N21 C31 120.3(5) . . ? N21 C22 C4 127.9(5) . . ? N21 C22 S23 111.5(4) . . ? C4 C22 S23 120.7(4) . . ? C24 S23 C22 91.5(3) . . ? C25 C24 C29 121.3(6) . . ? C25 C24 S23 110.3(4) . . ? C29 C24 S23 128.4(5) . . ? C26 C25 C24 121.1(6) . . ? C26 C25 N21 126.3(6) . . ? C24 C25 N21 112.7(5) . . ? C27 C26 C25 117.4(6) . . ? C26 C27 C28 122.6(6) . . ? C29 C28 C27 119.7(6) . . ? C29 C28 C32 120.4(6) . . ? C27 C28 C32 119.9(6) . . ? C28 C29 C24 118.0(6) . . ? Cl11 C10 Cl12 109.5 . . ? Cl11 C10 Cl13 109.4 . . ? Cl12 C10 Cl13 109.4 . . ? Cl22 C20 Cl21 109.5 . . ? Cl22 C20 Cl23 109.4 . . ? Cl21 C20 Cl23 109.4 . . ? Cl31 C30 Cl32 109.5 . . ? Cl31 C30 Cl33 109.4 . . ? Cl32 C30 Cl33 109.4 . . ? C30 Cl31 Cl31 136.8(2) . 2 ? Cl41 C40 Cl42 109.5 . . ? Cl41 C40 Cl43 109.4 . . ? Cl42 C40 Cl43 109.4 . . ? _chemical_name_common ; bis(2-(4-(dimethylamino)phenyl)-3,6-dimethylbenzo(d)thiazol-3- ium) tetraiodide, chloroform solvate 1:2 ; # Attachment 'cr07_0403091.cif' data_C2 _database_code_depnum_ccdc_archive 'CCDC 728299' _audit_creation_method SHELXL-97 _chemical_formula_moiety '(C17 H19 N2 S 1+), I 1-, (C H Cl3)' _chemical_formula_sum 'C18 H20 Cl3 I N2 S' _chemical_formula_weight 529.67 _chemical_name_systematic ; [2-(4-(dimethylamino)phenyl)-3,6-dimethylbenzo[d]thiazol-3-ium] iodide, chloroform solvate 1:1 ; 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 94.431(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.4500(5) _cell_length_b 14.7704(9) _cell_length_c 19.5483(12) _cell_measurement_reflns_used 3608 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 23.93 _cell_measurement_theta_min 2.25 _cell_volume 2144.7(2) _exptl_absorpt_coefficient_mu 1.969 _exptl_absorpt_correction_T_max 0.911 _exptl_absorpt_correction_T_min 0.515 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, 2.05' _exptl_crystal_F_000 1048 _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.05 _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 8.13 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.920 _diffrn_measurement_device_type 'Bruker SMART-APEX diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 14563 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.01 _diffrn_reflns_theta_min 1.73 _diffrn_standards_decay_% 0.4 _diffrn_standards_number 262 _reflns_number_gt 3608 _reflns_number_total 5255 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT 5.0 (Bruker)' _computing_data_collection 'SMART 5.6 (Bruker)' _computing_data_reduction 'SAINT 5.0 (Bruker)' _computing_molecular_graphics ; Olex2, Durham University (compiled Feb 15 2009 13:03:59) ; _computing_publication_material ; Olex2, Durham University (compiled Feb 15 2009 13:03:59) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.791 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.075 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0420 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 230 _refine_ls_number_reflns 5255 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.0956 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0412P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C1 C 0.9252(4) 0.8309(2) 0.10604(18) 0.0555(8) Uani 1 1 d . . . C2 C 0.9125(5) 0.8221(2) 0.03416(17) 0.0550(8) Uani 1 1 d . . . H2 H 0.9358 0.8722 0.0074 0.066 Uiso 1 1 calc R . . C3 C 0.8671(5) 0.7424(2) 0.00280(17) 0.0536(8) Uani 1 1 d . . . H3 H 0.8631 0.7390 -0.0448 0.064 Uiso 1 1 calc R . . C4 C 0.8262(4) 0.6650(2) 0.04009(16) 0.0473(7) Uani 1 1 d . . . C5 C 0.8446(5) 0.6737(3) 0.11144(17) 0.0571(9) Uani 1 1 d . . . H5 H 0.8232 0.6233 0.1381 0.069 Uiso 1 1 calc R . . C6 C 0.8923(5) 0.7525(3) 0.14375(18) 0.0615(9) Uani 1 1 d . . . H6 H 0.9034 0.7546 0.1914 0.074 Uiso 1 1 calc R . . N11 N 0.9682(4) 0.9104(2) 0.13731(15) 0.0709(9) Uani 1 1 d . . . C12 C 1.0148(7) 0.9148(3) 0.2104(2) 0.0993(16) Uani 1 1 d . . . H12B H 1.0527 0.9752 0.2227 0.149 Uiso 1 1 calc R . . H12C H 1.1109 0.8732 0.2226 0.149 Uiso 1 1 calc R . . H12A H 0.9117 0.8991 0.2345 0.149 Uiso 1 1 calc R . . C13 C 0.9893(6) 0.9929(3) 0.0984(2) 0.0832(12) Uani 1 1 d . . . H13B H 0.9889 1.0441 0.1286 0.125 Uiso 1 1 calc R . . H13C H 0.8917 0.9982 0.0636 0.125 Uiso 1 1 calc R . . H13A H 1.1014 0.9909 0.0772 0.125 Uiso 1 1 calc R . . N21 N 0.7051(3) 0.56267(18) -0.05351(13) 0.0488(6) Uani 1 1 d . . . C22 C 0.7764(4) 0.5794(2) 0.00969(15) 0.0446(7) Uani 1 1 d . . . S23 S 0.80959(11) 0.48041(6) 0.05685(4) 0.0499(2) Uani 1 1 d . . . C24 C 0.7232(4) 0.4153(2) -0.01249(15) 0.0464(7) Uani 1 1 d . . . C25 C 0.6799(4) 0.4709(2) -0.06865(16) 0.0473(7) Uani 1 1 d . . . C26 C 0.6170(5) 0.4333(3) -0.13098(17) 0.0611(9) Uani 1 1 d . . . H26 H 0.5895 0.4694 -0.1693 0.073 Uiso 1 1 calc R . . C27 C 0.5965(5) 0.3414(3) -0.13424(19) 0.0655(10) Uani 1 1 d . . . H27 H 0.5553 0.3156 -0.1759 0.079 Uiso 1 1 calc R . . C28 C 0.6342(4) 0.2846(2) -0.07843(19) 0.0572(8) Uani 1 1 d . . . C29 C 0.6988(4) 0.3222(2) -0.01694(17) 0.0523(8) Uani 1 1 d . . . H29 H 0.7258 0.2856 0.0212 0.063 Uiso 1 1 calc R . . C31 C 0.6389(5) 0.6329(2) -0.10327(17) 0.0604(9) Uani 1 1 d . . . H31C H 0.5324 0.6114 -0.1290 0.091 Uiso 1 1 calc R . . H31B H 0.7301 0.6456 -0.1340 0.091 Uiso 1 1 calc R . . H31A H 0.6113 0.6870 -0.0791 0.091 Uiso 1 1 calc R . . C32 C 0.5998(5) 0.1847(3) -0.0848(2) 0.0737(11) Uani 1 1 d . . . H32A H 0.6230 0.1649 -0.1301 0.111 Uiso 1 1 calc R . . H32C H 0.4766 0.1723 -0.0769 0.111 Uiso 1 1 calc R . . H32B H 0.6777 0.1529 -0.0516 0.111 Uiso 1 1 calc R . . I1 I 0.88007(3) 0.282040(16) 0.177940(11) 0.06028(10) Uani 1 1 d . . . C10 C 0.9820(6) 0.6008(3) 0.3263(2) 0.0769(11) Uani 1 1 d . . . H10 H 0.8788 0.6413 0.3171 0.092 Uiso 1 1 calc R . . Cl11 Cl 1.17977(16) 0.65805(7) 0.30851(6) 0.0873(3) Uani 1 1 d . . . Cl12 Cl 0.9519(2) 0.50429(8) 0.27473(7) 0.1027(4) Uani 1 1 d . . . Cl13 Cl 0.99677(19) 0.56955(10) 0.41325(7) 0.1098(4) 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 C1 0.0459(19) 0.069(2) 0.052(2) -0.0029(17) 0.0067(15) -0.0030(17) C2 0.058(2) 0.059(2) 0.048(2) 0.0065(16) 0.0092(16) -0.0057(17) C3 0.052(2) 0.068(2) 0.0407(18) 0.0020(16) 0.0068(14) 0.0001(17) C4 0.0394(17) 0.060(2) 0.0434(18) 0.0047(15) 0.0073(13) -0.0003(15) C5 0.058(2) 0.069(2) 0.0447(19) 0.0096(17) 0.0024(16) -0.0076(18) C6 0.069(2) 0.080(2) 0.0359(18) 0.0020(17) 0.0037(16) -0.011(2) N11 0.082(2) 0.077(2) 0.0541(19) -0.0130(16) 0.0122(16) -0.0176(18) C12 0.130(4) 0.113(4) 0.056(3) -0.023(2) 0.013(3) -0.045(3) C13 0.092(3) 0.067(3) 0.092(3) -0.013(2) 0.010(2) -0.014(2) N21 0.0406(14) 0.0665(18) 0.0393(15) 0.0081(12) 0.0023(11) -0.0005(13) C22 0.0358(16) 0.0611(19) 0.0379(17) 0.0089(14) 0.0086(12) 0.0027(14) S23 0.0495(5) 0.0588(5) 0.0410(4) 0.0060(4) 0.0020(3) 0.0028(4) C24 0.0331(16) 0.062(2) 0.0445(18) 0.0000(15) 0.0054(12) 0.0042(14) C25 0.0375(16) 0.061(2) 0.0440(18) 0.0021(15) 0.0072(13) -0.0001(15) C26 0.066(2) 0.075(3) 0.0410(19) 0.0062(17) -0.0014(16) -0.0083(19) C27 0.059(2) 0.088(3) 0.050(2) -0.012(2) 0.0047(17) -0.009(2) C28 0.0452(19) 0.069(2) 0.058(2) -0.0061(18) 0.0123(16) -0.0036(17) C29 0.0418(18) 0.060(2) 0.056(2) 0.0024(16) 0.0089(15) 0.0049(16) C31 0.057(2) 0.074(2) 0.048(2) 0.0162(17) -0.0073(16) -0.0051(19) C32 0.065(3) 0.074(2) 0.082(3) -0.014(2) 0.008(2) -0.006(2) I1 0.05806(16) 0.07322(18) 0.05039(15) 0.00390(11) 0.00948(10) 0.00026(12) C10 0.070(3) 0.072(3) 0.088(3) -0.006(2) 0.002(2) 0.004(2) Cl11 0.0855(7) 0.0710(7) 0.1066(9) -0.0032(6) 0.0161(6) -0.0041(6) Cl12 0.1179(10) 0.0806(7) 0.1067(10) -0.0166(6) -0.0108(8) -0.0111(7) Cl13 0.1060(10) 0.1407(12) 0.0840(9) 0.0035(8) 0.0161(7) -0.0024(9) _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 C1 N11 1.351(4) . ? C1 C6 1.404(5) . ? C1 C2 1.407(5) . ? C2 C3 1.358(5) . ? C3 C4 1.402(4) . ? C4 C5 1.397(4) . ? C4 C22 1.434(5) . ? C5 C6 1.358(5) . ? N11 C12 1.445(5) . ? N11 C13 1.451(5) . ? N21 C22 1.330(4) . ? N21 C25 1.397(4) . ? N21 C31 1.480(4) . ? C22 S23 1.736(3) . ? S23 C24 1.744(3) . ? C24 C25 1.389(4) . ? C24 C29 1.390(5) . ? C25 C26 1.388(4) . ? C26 C27 1.367(5) . ? C27 C28 1.388(5) . ? C28 C29 1.377(5) . ? C28 C32 1.501(5) . ? C10 Cl12 1.750(4) . ? C10 Cl11 1.757(4) . ? C10 Cl13 1.757(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 N11 C1 C6 121.6(3) . . ? N11 C1 C2 121.8(3) . . ? C6 C1 C2 116.6(3) . . ? C3 C2 C1 121.7(3) . . ? C2 C3 C4 121.9(3) . . ? C5 C4 C3 115.8(3) . . ? C5 C4 C22 119.9(3) . . ? C3 C4 C22 124.3(3) . . ? C6 C5 C4 123.1(3) . . ? C5 C6 C1 120.8(3) . . ? C1 N11 C12 121.1(3) . . ? C1 N11 C13 121.6(3) . . ? C12 N11 C13 116.9(3) . . ? C22 N21 C25 114.5(3) . . ? C22 N21 C31 124.7(3) . . ? C25 N21 C31 120.5(3) . . ? N21 C22 C4 128.4(3) . . ? N21 C22 S23 111.6(2) . . ? C4 C22 S23 120.1(2) . . ? C22 S23 C24 91.28(15) . . ? C25 C24 C29 121.0(3) . . ? C25 C24 S23 109.7(2) . . ? C29 C24 S23 129.3(3) . . ? C26 C25 C24 120.0(3) . . ? C26 C25 N21 127.3(3) . . ? C24 C25 N21 112.8(3) . . ? C27 C26 C25 117.9(3) . . ? C26 C27 C28 123.3(3) . . ? C29 C28 C27 118.6(3) . . ? C29 C28 C32 121.0(4) . . ? C27 C28 C32 120.4(3) . . ? C28 C29 C24 119.3(3) . . ? Cl12 C10 Cl11 110.5(2) . . ? Cl12 C10 Cl13 109.8(2) . . ? Cl11 C10 Cl13 109.1(2) . . ? _chemical_name_common ; (2-(4-(dimethylamino)phenyl)-3,6-dimethylbenzo(d)thiazol-3- ium) iodide, chloroform solvate 1:1 ;