# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'ProfD Nikolay Gerasimchuk' _publ_contact_author_email NNGERASIMCHUK@MISSOURISTATE.EDU _publ_section_title ; Benz(2-heteroaryl)cyanoximes and their Tl(I) complexes: new room temperature blue emitters. ; _publ_contact_author_address ; Department of Chemistry, Temple Hall 456, Missouri State University, Springfield, MO 65897, USA. ; _publ_contact_author_fax '1 417 836 5507' _publ_contact_author_phone '1 417 836 5165' _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. ; loop_ _publ_author_name 'Nikolay Gerasimchuk' 'Steve Archibald' 'Charles L. Barnes' 'Richard Biagioni' ; O.A.Gerasimchuk ; 'Olesya T. Ilkun' 'Svitlana Silchenko' # Attachment 'HBIMCO_H2O-final.cif' data_HBIMCO_H2O-final _database_code_depnum_ccdc_archive 'CCDC 680405' _audit_creation_method SHELXL-97 _chemical_name_systematic ; alpha-oximino(N-methyl-2-benzimidazolyl)-acetonitrile ; _chemical_formula_moiety 'C10 H8 N4 O, H2 O' _chemical_formula_sum 'C10 H10 N4 O2' _chemical_formula_weight 218.22 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1446(18) _cell_length_b 8.587(2) _cell_length_c 8.988(2) _cell_angle_alpha 96.67(2) _cell_angle_beta 109.370(18) _cell_angle_gamma 99.79(2) _cell_volume 503.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 158 _cell_measurement_theta_min 6.17 _cell_measurement_theta_max 65.53 _exptl_crystal_description lathe _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe IPDS-II image plate' _diffrn_measurement_method '\w scans, 160 frames at 2\% intervals, exposure time 8 minutes' _diffrn_reflns_number 13006 _diffrn_reflns_av_R_equivalents 0.0692 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 34.75 _reflns_number_total 4301 _reflns_number_gt 2326 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'SHELXL97(Sheldrick, 1997) and WinGX (Farrugia, 1999)' _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^)+(0.0854P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.084(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4301 _refine_ls_number_parameters 155 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1169 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1687 _refine_ls_wR_factor_gt 0.1389 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 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 0.2744(2) 0.57908(18) 0.52010(17) 0.0225(3) Uani 1 1 d . . . C2 C 0.3897(2) 0.71748(18) 0.64780(17) 0.0241(3) Uani 1 1 d . . . C3 C 0.5153(2) 0.68307(18) 0.79882(19) 0.0265(3) Uani 1 1 d . . . C4 C 0.1606(2) 0.33327(18) 0.39729(17) 0.0236(3) Uani 1 1 d . . . C5 C 0.0663(2) 0.42802(18) 0.29018(17) 0.0232(3) Uani 1 1 d . . . C6 C -0.0738(2) 0.3608(2) 0.13654(18) 0.0266(3) Uani 1 1 d . . . H6 H -0.1366 0.4241 0.0667 0.032 Uiso 1 1 calc R . . C7 C -0.1146(3) 0.1954(2) 0.09348(19) 0.0299(3) Uani 1 1 d . . . H7 H -0.2070 0.1464 -0.0083 0.036 Uiso 1 1 calc R . . C8 C -0.0213(3) 0.09888(19) 0.1984(2) 0.0296(3) Uani 1 1 d . . . H8 H -0.0527 -0.0120 0.1643 0.036 Uiso 1 1 calc R . . C9 C 0.1168(2) 0.16552(19) 0.35150(19) 0.0271(3) Uani 1 1 d . . . H9 H 0.1779 0.1015 0.4212 0.033 Uiso 1 1 calc R . . C10 C 0.0853(3) 0.72564(19) 0.30663(19) 0.0272(3) Uani 1 1 d . . . H10A H -0.0110 0.6915 0.1988 0.041 Uiso 1 1 calc R . . H10B H 0.2043 0.7969 0.3065 0.041 Uiso 1 1 calc R . . H10C H 0.0252 0.7807 0.3717 0.041 Uiso 1 1 calc R . . N1 N 0.28965(19) 0.43116(15) 0.54050(15) 0.0240(2) Uani 1 1 d . . . N2 N 0.1423(2) 0.58535(15) 0.37199(15) 0.0232(2) Uani 1 1 d . . . N3 N 0.3777(2) 0.86264(16) 0.63125(16) 0.0281(3) Uani 1 1 d . . . N4 N 0.6109(2) 0.65835(19) 0.91983(17) 0.0337(3) Uani 1 1 d . . . O1 O 0.49954(19) 0.97053(14) 0.76659(15) 0.0334(3) Uani 1 1 d D . . O2 O 0.4655(2) 1.26288(16) 0.77472(16) 0.0376(3) Uani 1 1 d D . . H1 H 0.467(4) 1.074(2) 0.747(3) 0.045 Uiso 1 1 d D . . H1W H 0.414(4) 1.326(3) 0.702(3) 0.056 Uiso 1 1 d D . . H2W H 0.437(4) 1.300(3) 0.863(3) 0.056 Uiso 1 1 d 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 0.0231(6) 0.0242(6) 0.0214(6) 0.0054(5) 0.0086(5) 0.0064(5) C2 0.0234(6) 0.0261(7) 0.0222(6) 0.0050(5) 0.0071(5) 0.0057(5) C3 0.0266(7) 0.0251(7) 0.0262(7) 0.0028(5) 0.0084(6) 0.0050(5) C4 0.0244(6) 0.0259(7) 0.0211(6) 0.0050(5) 0.0077(5) 0.0070(5) C5 0.0245(6) 0.0242(6) 0.0220(6) 0.0042(5) 0.0092(5) 0.0069(5) C6 0.0268(7) 0.0303(7) 0.0215(6) 0.0052(5) 0.0067(5) 0.0071(6) C7 0.0296(8) 0.0320(8) 0.0238(7) 0.0008(6) 0.0065(6) 0.0050(6) C8 0.0328(8) 0.0244(7) 0.0289(7) 0.0001(6) 0.0095(6) 0.0055(6) C9 0.0306(7) 0.0253(7) 0.0260(7) 0.0055(5) 0.0097(6) 0.0081(6) C10 0.0321(8) 0.0246(7) 0.0248(7) 0.0083(5) 0.0074(6) 0.0089(6) N1 0.0256(6) 0.0236(6) 0.0228(6) 0.0055(4) 0.0073(5) 0.0071(5) N2 0.0252(6) 0.0227(5) 0.0210(5) 0.0055(4) 0.0066(4) 0.0060(4) N3 0.0284(6) 0.0257(6) 0.0266(6) 0.0029(5) 0.0061(5) 0.0054(5) N4 0.0346(7) 0.0374(8) 0.0269(6) 0.0072(6) 0.0071(5) 0.0091(6) O1 0.0357(6) 0.0231(5) 0.0316(6) 0.0017(4) 0.0014(5) 0.0051(5) O2 0.0555(8) 0.0322(6) 0.0268(6) 0.0091(5) 0.0105(6) 0.0203(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.322(2) . ? C1 N2 1.366(2) . ? C1 C2 1.460(2) . ? C2 N3 1.286(2) . ? C2 C3 1.453(2) . ? C3 N4 1.142(2) . ? C4 N1 1.383(2) . ? C4 C9 1.402(2) . ? C4 C5 1.407(2) . ? C5 N2 1.384(2) . ? C5 C6 1.394(2) . ? C6 C7 1.382(2) . ? C7 C8 1.405(2) . ? C8 C9 1.385(2) . ? C10 N2 1.461(2) . ? N3 O1 1.3629(19) . ? 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 N1 C1 N2 113.23(13) . . ? N1 C1 C2 121.25(13) . . ? N2 C1 C2 125.52(13) . . ? N3 C2 C3 120.93(14) . . ? N3 C2 C1 122.55(14) . . ? C3 C2 C1 116.48(13) . . ? N4 C3 C2 177.96(17) . . ? N1 C4 C9 129.91(14) . . ? N1 C4 C5 109.62(13) . . ? C9 C4 C5 120.47(14) . . ? N2 C5 C6 132.21(14) . . ? N2 C5 C4 105.61(13) . . ? C6 C5 C4 122.18(14) . . ? C7 C6 C5 116.50(15) . . ? C6 C7 C8 122.17(15) . . ? C9 C8 C7 121.33(15) . . ? C8 C9 C4 117.35(15) . . ? C1 N1 C4 105.17(12) . . ? C1 N2 C5 106.36(12) . . ? C1 N2 C10 128.94(13) . . ? C5 N2 C10 124.69(13) . . ? C2 N3 O1 111.61(13) . . ? 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 N1 C1 C2 N3 -179.94(15) . . . . ? N2 C1 C2 N3 -0.4(2) . . . . ? N1 C1 C2 C3 -2.1(2) . . . . ? N2 C1 C2 C3 177.42(14) . . . . ? N1 C4 C5 N2 0.27(16) . . . . ? C9 C4 C5 N2 -179.96(13) . . . . ? N1 C4 C5 C6 -179.30(14) . . . . ? C9 C4 C5 C6 0.5(2) . . . . ? N2 C5 C6 C7 179.95(15) . . . . ? C4 C5 C6 C7 -0.6(2) . . . . ? C5 C6 C7 C8 0.3(2) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C7 C8 C9 C4 -0.4(2) . . . . ? N1 C4 C9 C8 179.77(14) . . . . ? C5 C4 C9 C8 0.1(2) . . . . ? N2 C1 N1 C4 0.22(16) . . . . ? C2 C1 N1 C4 179.77(13) . . . . ? C9 C4 N1 C1 179.96(16) . . . . ? C5 C4 N1 C1 -0.30(16) . . . . ? N1 C1 N2 C5 -0.05(17) . . . . ? C2 C1 N2 C5 -179.58(13) . . . . ? N1 C1 N2 C10 179.51(14) . . . . ? C2 C1 N2 C10 0.0(2) . . . . ? C6 C5 N2 C1 179.37(16) . . . . ? C4 C5 N2 C1 -0.14(15) . . . . ? C6 C5 N2 C10 -0.2(2) . . . . ? C4 C5 N2 C10 -179.72(13) . . . . ? C3 C2 N3 O1 2.3(2) . . . . ? C1 C2 N3 O1 -179.90(13) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 34.75 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.367 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.075 _chemical_name_common alpha-oximino(N-methyl-2-benzimidazolyl)-acetonitrile # Attachment 'HBOCO_ion_pair-final.cif' data_HBOCO_ion_pair-final _database_code_depnum_ccdc_archive 'CCDC 680406' _audit_creation_method SHELXL-97 _chemical_name_systematic ; alfa-Oximino(2-benzoxazolyl)-acetonitrile ; _chemical_name_common alfa-Oximino(2-benzoxazolyl)-acetonitrile _chemical_melting_point '> 195 decomposes' _chemical_formula_moiety 'C9 H6 N3 O2, C9 H4 N3 O2' _chemical_formula_sum 'C18 H10 N6 O4' _chemical_formula_weight 374.32 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 14.1723(19) _cell_length_b 7.1591(10) _cell_length_c 17.461(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.404(2) _cell_angle_gamma 90.00 _cell_volume 1736.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 149 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.3 _exptl_crystal_description plate _exptl_crystal_colour brown-orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9048 _exptl_absorpt_correction_T_max 0.9947 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _diffrn_ambient_temperature 173(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 APEX2 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 11651 _diffrn_reflns_av_R_equivalents 0.0846 _diffrn_reflns_av_sigmaI/netI 0.1261 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 27.13 _reflns_number_total 3815 _reflns_number_gt 1506 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0917P)^2^+1.7467P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens noref _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0018(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3815 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2129 _refine_ls_R_factor_gt 0.0708 _refine_ls_wR_factor_ref 0.2407 _refine_ls_wR_factor_gt 0.1707 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 C1A C 0.6807(3) 0.5219(6) 0.8850(2) 0.0382(11) Uani 1 1 d . . . C2A C 0.6825(4) 0.4567(6) 1.0062(3) 0.0427(12) Uani 1 1 d . . . C3A C 0.6588(4) 0.4309(7) 1.0786(3) 0.0547(14) Uani 1 1 d . . . H3A H 0.5969 0.4580 1.0890 0.066 Uiso 1 1 calc R . . C4A C 0.7334(5) 0.3621(8) 1.1341(3) 0.0609(15) Uani 1 1 d . . . H4A H 0.7223 0.3396 1.1851 0.073 Uiso 1 1 calc R . . C5A C 0.8237(4) 0.3240(7) 1.1193(3) 0.0604(16) Uani 1 1 d . . . H5A H 0.8721 0.2771 1.1603 0.072 Uiso 1 1 calc R . . C6A C 0.8458(4) 0.3524(7) 1.0460(3) 0.0527(14) Uani 1 1 d . . . H6A H 0.9079 0.3274 1.0358 0.063 Uiso 1 1 calc R . . C7A C 0.7713(4) 0.4195(6) 0.9890(3) 0.0411(12) Uani 1 1 d . . . C8A C 0.6399(4) 0.5922(6) 0.8092(3) 0.0413(12) Uani 1 1 d . . . C9A C 0.5448(4) 0.6653(7) 0.7926(3) 0.0453(13) Uani 1 1 d . . . C1B C 0.8754(3) 0.6796(6) 0.5853(2) 0.0364(11) Uani 1 1 d . . . C2B C 0.8018(3) 0.5821(6) 0.4709(3) 0.0376(11) Uani 1 1 d . . . C3B C 0.7774(4) 0.5294(6) 0.3942(3) 0.0432(12) Uani 1 1 d . . . H3B H 0.8218 0.5338 0.3599 0.052 Uiso 1 1 calc R . . C4B C 0.6840(4) 0.4697(7) 0.3701(3) 0.0478(13) Uani 1 1 d . . . H4B H 0.6630 0.4310 0.3175 0.057 Uiso 1 1 calc R . . C5B C 0.6198(4) 0.4643(7) 0.4203(3) 0.0541(14) Uani 1 1 d . . . H5B H 0.5561 0.4213 0.4011 0.065 Uiso 1 1 calc R . . C6B C 0.6451(4) 0.5194(7) 0.4974(3) 0.0498(13) Uani 1 1 d . . . H6B H 0.6005 0.5167 0.5315 0.060 Uiso 1 1 calc R . . C7B C 0.7399(3) 0.5791(6) 0.5225(2) 0.0365(11) Uani 1 1 d . . . C8B C 0.9539(3) 0.7557(6) 0.6416(3) 0.0382(11) Uani 1 1 d . . . C9B C 0.9417(3) 0.7918(7) 0.7196(3) 0.0436(12) Uani 1 1 d . . . N1A N 0.7679(3) 0.4637(5) 0.9102(2) 0.0398(10) Uani 1 1 d . . . N2A N 0.7083(4) 0.5873(6) 0.7579(2) 0.0804(19) Uani 1 1 d . . . N3A N 0.4681(4) 0.7252(7) 0.7804(2) 0.0639(13) Uani 1 1 d . . . N1B N 0.7898(3) 0.6423(5) 0.5953(2) 0.0411(10) Uani 1 1 d . . . H1B H 0.7674 0.6539 0.6385 0.049 Uiso 1 1 calc R . . N2B N 1.0329(3) 0.7982(5) 0.6190(2) 0.0415(10) Uani 1 1 d . . . N3B N 0.9344(3) 0.8268(7) 0.7817(3) 0.0649(13) Uani 1 1 d . . . O1A O 0.6228(2) 0.5234(4) 0.93826(17) 0.0434(8) Uani 1 1 d . . . O2A O 0.6622(3) 0.6617(6) 0.6949(3) 0.0807(13) Uani 1 1 d . . . O1B O 0.8904(2) 0.6478(4) 0.51164(16) 0.0394(8) Uani 1 1 d . . . O2B O 1.0995(2) 0.8712(5) 0.67757(18) 0.0493(9) Uani 1 1 d . . . H2B H 1.1495 0.8972 0.6608 0.074 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 C1A 0.051(3) 0.028(3) 0.039(3) -0.003(2) 0.017(2) -0.004(2) C2A 0.056(3) 0.031(3) 0.040(3) -0.001(2) 0.007(2) -0.002(2) C3A 0.070(4) 0.053(4) 0.046(3) -0.007(3) 0.021(3) 0.001(3) C4A 0.077(4) 0.054(4) 0.050(3) -0.006(3) 0.010(3) -0.001(3) C5A 0.081(4) 0.038(3) 0.052(3) -0.003(3) -0.012(3) -0.003(3) C6A 0.060(3) 0.034(3) 0.059(3) -0.006(2) -0.002(3) -0.003(3) C7A 0.052(3) 0.025(3) 0.047(3) -0.006(2) 0.012(2) -0.007(2) C8A 0.055(3) 0.037(3) 0.037(3) -0.002(2) 0.019(2) -0.009(2) C9A 0.057(4) 0.039(3) 0.038(3) 0.002(2) 0.004(2) -0.009(3) C1B 0.044(3) 0.032(3) 0.036(3) 0.001(2) 0.015(2) 0.001(2) C2B 0.040(3) 0.024(2) 0.047(3) 0.004(2) 0.005(2) 0.001(2) C3B 0.054(3) 0.034(3) 0.040(3) 0.003(2) 0.007(2) 0.004(2) C4B 0.056(3) 0.035(3) 0.048(3) 0.004(2) -0.001(3) 0.006(3) C5B 0.052(3) 0.040(3) 0.065(4) 0.001(3) 0.000(3) 0.003(3) C6B 0.045(3) 0.039(3) 0.068(3) 0.000(3) 0.015(3) -0.001(3) C7B 0.041(3) 0.028(3) 0.040(3) 0.004(2) 0.007(2) 0.004(2) C8B 0.040(3) 0.034(3) 0.043(3) 0.005(2) 0.013(2) 0.002(2) C9B 0.048(3) 0.044(3) 0.041(3) 0.000(2) 0.014(2) 0.000(2) N1A 0.042(2) 0.030(2) 0.049(2) -0.0029(18) 0.0130(18) -0.0054(19) N2A 0.158(5) 0.026(2) 0.037(2) 0.011(2) -0.028(3) -0.029(3) N3A 0.065(3) 0.056(3) 0.062(3) 0.003(2) -0.008(2) 0.000(3) N1B 0.050(3) 0.037(2) 0.040(2) -0.0004(18) 0.0187(19) 0.000(2) N2B 0.046(3) 0.033(2) 0.044(2) -0.0003(18) 0.0039(19) -0.0021(19) N3B 0.074(3) 0.071(4) 0.055(3) -0.007(2) 0.025(2) -0.002(3) O1A 0.048(2) 0.040(2) 0.0449(18) -0.0023(15) 0.0165(16) -0.0017(16) O2A 0.066(3) 0.067(3) 0.101(3) -0.014(3) -0.003(2) 0.003(2) O1B 0.044(2) 0.0368(19) 0.0392(18) 0.0026(14) 0.0118(14) 0.0015(15) O2B 0.042(2) 0.053(2) 0.053(2) -0.0040(17) 0.0092(16) -0.0070(17) _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 C1A N1A 1.296(6) . ? C1A O1A 1.356(5) . ? C1A C8A 1.428(6) . ? C2A C7A 1.377(6) . ? C2A C3A 1.383(6) . ? C2A O1A 1.399(5) . ? C3A C4A 1.377(7) . ? C3A H3A 0.9500 . ? C4A C5A 1.382(8) . ? C4A H4A 0.9500 . ? C5A C6A 1.390(7) . ? C5A H5A 0.9500 . ? C6A C7A 1.386(7) . ? C6A H6A 0.9500 . ? C7A N1A 1.404(6) . ? C8A C9A 1.422(7) . ? C8A N2A 1.444(7) . ? C9A N3A 1.149(6) . ? C1B N1B 1.287(5) . ? C1B O1B 1.363(5) . ? C1B C8B 1.439(6) . ? C2B C3B 1.368(6) . ? C2B C7B 1.376(6) . ? C2B O1B 1.397(5) . ? C3B C4B 1.375(7) . ? C3B H3B 0.9500 . ? C4B C5B 1.384(7) . ? C4B H4B 0.9500 . ? C5B C6B 1.381(7) . ? C5B H5B 0.9500 . ? C6B C7B 1.395(6) . ? C6B H6B 0.9500 . ? C7B N1B 1.402(5) . ? C8B N2B 1.294(6) . ? C8B C9B 1.430(6) . ? C9B N3B 1.137(5) . ? N2A O2A 1.280(5) . ? N1B H1B 0.8800 . ? N2B O2B 1.352(4) . ? O2B H2B 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1A C1A O1A 115.9(4) . . ? N1A C1A C8A 127.7(4) . . ? O1A C1A C8A 116.3(4) . . ? C7A C2A C3A 124.9(5) . . ? C7A C2A O1A 107.9(4) . . ? C3A C2A O1A 127.2(5) . . ? C4A C3A C2A 113.5(5) . . ? C4A C3A H3A 123.2 . . ? C2A C3A H3A 123.2 . . ? C3A C4A C5A 123.4(5) . . ? C3A C4A H4A 118.3 . . ? C5A C4A H4A 118.3 . . ? C4A C5A C6A 121.9(5) . . ? C4A C5A H5A 119.0 . . ? C6A C5A H5A 119.0 . . ? C7A C6A C5A 115.7(5) . . ? C7A C6A H6A 122.1 . . ? C5A C6A H6A 122.1 . . ? C2A C7A C6A 120.6(5) . . ? C2A C7A N1A 108.3(4) . . ? C6A C7A N1A 131.0(5) . . ? C9A C8A C1A 120.8(4) . . ? C9A C8A N2A 127.6(4) . . ? C1A C8A N2A 111.5(4) . . ? N3A C9A C8A 179.0(5) . . ? N1B C1B O1B 114.8(4) . . ? N1B C1B C8B 127.4(4) . . ? O1B C1B C8B 117.7(4) . . ? C3B C2B C7B 124.5(4) . . ? C3B C2B O1B 128.3(4) . . ? C7B C2B O1B 107.2(4) . . ? C2B C3B C4B 115.2(4) . . ? C2B C3B H3B 122.4 . . ? C4B C3B H3B 122.4 . . ? C3B C4B C5B 122.0(5) . . ? C3B C4B H4B 119.0 . . ? C5B C4B H4B 119.0 . . ? C6B C5B C4B 122.2(5) . . ? C6B C5B H5B 118.9 . . ? C4B C5B H5B 118.9 . . ? C5B C6B C7B 116.2(5) . . ? C5B C6B H6B 121.9 . . ? C7B C6B H6B 121.9 . . ? C2B C7B C6B 119.9(4) . . ? C2B C7B N1B 108.4(4) . . ? C6B C7B N1B 131.7(4) . . ? N2B C8B C9B 121.5(4) . . ? N2B C8B C1B 118.6(4) . . ? C9B C8B C1B 119.8(4) . . ? N3B C9B C8B 177.1(5) . . ? C1A N1A C7A 104.5(4) . . ? O2A N2A C8A 103.3(5) . . ? C1B N1B C7B 105.3(4) . . ? C1B N1B H1B 127.3 . . ? C7B N1B H1B 127.3 . . ? C8B N2B O2B 112.2(4) . . ? C1A O1A C2A 103.4(3) . . ? C1B O1B C2B 104.2(3) . . ? N2B O2B H2B 109.5 . . ? 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 C7A C2A C3A C4A -0.2(7) . . . . ? O1A C2A C3A C4A 179.7(5) . . . . ? C2A C3A C4A C5A 0.6(8) . . . . ? C3A C4A C5A C6A -0.2(8) . . . . ? C4A C5A C6A C7A -0.5(7) . . . . ? C3A C2A C7A C6A -0.6(7) . . . . ? O1A C2A C7A C6A 179.5(4) . . . . ? C3A C2A C7A N1A -179.8(4) . . . . ? O1A C2A C7A N1A 0.4(5) . . . . ? C5A C6A C7A C2A 0.9(7) . . . . ? C5A C6A C7A N1A 179.9(4) . . . . ? N1A C1A C8A C9A -174.7(5) . . . . ? O1A C1A C8A C9A 2.2(6) . . . . ? N1A C1A C8A N2A 2.0(7) . . . . ? O1A C1A C8A N2A 178.9(4) . . . . ? C7B C2B C3B C4B -0.4(7) . . . . ? O1B C2B C3B C4B 179.9(4) . . . . ? C2B C3B C4B C5B 0.2(7) . . . . ? C3B C4B C5B C6B 0.4(8) . . . . ? C4B C5B C6B C7B -0.7(7) . . . . ? C3B C2B C7B C6B 0.0(7) . . . . ? O1B C2B C7B C6B 179.8(4) . . . . ? C3B C2B C7B N1B -180.0(4) . . . . ? O1B C2B C7B N1B -0.2(5) . . . . ? C5B C6B C7B C2B 0.5(7) . . . . ? C5B C6B C7B N1B -179.5(4) . . . . ? N1B C1B C8B N2B -174.4(4) . . . . ? O1B C1B C8B N2B 3.1(6) . . . . ? N1B C1B C8B C9B 2.3(7) . . . . ? O1B C1B C8B C9B 179.9(4) . . . . ? O1A C1A N1A C7A 0.2(5) . . . . ? C8A C1A N1A C7A 177.1(4) . . . . ? C2A C7A N1A C1A -0.3(5) . . . . ? C6A C7A N1A C1A -179.4(5) . . . . ? C9A C8A N2A O2A -0.8(6) . . . . ? C1A C8A N2A O2A -177.2(4) . . . . ? O1B C1B N1B C7B -0.1(5) . . . . ? C8B C1B N1B C7B 177.5(4) . . . . ? C2B C7B N1B C1B 0.2(5) . . . . ? C6B C7B N1B C1B -179.8(5) . . . . ? C9B C8B N2B O2B 2.2(6) . . . . ? C1B C8B N2B O2B 178.9(4) . . . . ? N1A C1A O1A C2A 0.0(5) . . . . ? C8A C1A O1A C2A -177.3(4) . . . . ? C7A C2A O1A C1A -0.2(5) . . . . ? C3A C2A O1A C1A 179.9(5) . . . . ? N1B C1B O1B C2B 0.0(5) . . . . ? C8B C1B O1B C2B -177.8(4) . . . . ? C3B C2B O1B C1B 179.9(4) . . . . ? C7B C2B O1B C1B 0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.13 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.798 _refine_diff_density_min -0.543 _refine_diff_density_rms 0.078 # Attachment 'TlBTCO-final.cif' data_Tl(BTCO)-final _database_code_depnum_ccdc_archive 'CCDC 680407' _audit_creation_method SHELXL-97 _chemical_name_common Tl-BTCO _chemical_formula_moiety 'C9 H4 N3 O S Tl' _chemical_formula_sum 'C9 H4 N3 O S Tl' _chemical_formula_weight 406.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 14.8621(17) _cell_length_b 4.4277(3) _cell_length_c 15.0453(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.150(9) _cell_angle_gamma 90.00 _cell_volume 990.05(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 336 _cell_measurement_theta_min 6.32 _cell_measurement_theta_max 63.29 _exptl_crystal_description lathe _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 2.728 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 16.496 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.0536 _exptl_absorpt_correction_T_max 0.2167 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe IPDS-II image plate' _diffrn_measurement_method '\w scans, 220 frames at 1\% intervals, exposure time 2 minutes' _diffrn_reflns_number 19093 _diffrn_reflns_av_R_equivalents 0.0950 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 34.78 _reflns_number_total 4236 _reflns_number_gt 2987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'SHELXL97(Sheldrick, 1997) and WinGX (Farrugia, 1999)' _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^)+(0.1212P)^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 SHELXL _refine_ls_extinction_coef 0.0144(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4236 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1888 _refine_ls_wR_factor_gt 0.1698 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.023 _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 -0.40635(2) -0.30078(8) 0.593529(19) 0.03719(14) Uani 1 1 d . . . C1 C -0.2793(7) -0.7094(19) 0.2958(6) 0.0371(16) Uani 1 1 d . . . C2 C -0.3461(6) -0.8175(18) 0.3572(5) 0.0342(15) Uani 1 1 d . . . C3 C -0.4081(6) -1.0487(18) 0.3317(5) 0.0363(15) Uani 1 1 d . . . C4 C -0.2067(6) -0.614(2) 0.1710(6) 0.0365(14) Uani 1 1 d . . . C5 C -0.1546(6) -0.435(2) 0.2277(5) 0.0374(15) Uani 1 1 d . . . C6 C -0.0829(7) -0.264(2) 0.1972(9) 0.047(2) Uani 1 1 d . . . H6 H -0.0478 -0.1435 0.2364 0.056 Uiso 1 1 calc R . . C7 C -0.0647(8) -0.276(3) 0.1071(9) 0.052(3) Uani 1 1 d . . . H7 H -0.0162 -0.1606 0.0841 0.062 Uiso 1 1 calc R . . C8 C -0.1153(8) -0.453(3) 0.0493(7) 0.051(2) Uani 1 1 d . . . H8 H -0.1007 -0.4600 -0.0121 0.062 Uiso 1 1 calc R . . C9 C -0.1874(7) -0.621(3) 0.0815(6) 0.047(2) Uani 1 1 d . . . H9 H -0.2231 -0.7386 0.0421 0.056 Uiso 1 1 calc R . . N1 N -0.2778(6) -0.7662(17) 0.2112(5) 0.0379(14) Uani 1 1 d . . . N2 N -0.3527(6) -0.6834(16) 0.4352(4) 0.0360(14) Uani 1 1 d . . . N3 N -0.4605(7) -1.2332(18) 0.3173(6) 0.0414(16) Uani 1 1 d . . . O1 O -0.4198(6) -0.7694(15) 0.4864(4) 0.0404(13) Uani 1 1 d . . . S1 S -0.19562(16) -0.4622(5) 0.33599(14) 0.0413(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 Tl1 0.0444(2) 0.0331(2) 0.03410(17) -0.00075(10) -0.00133(11) 0.00022(12) C1 0.049(4) 0.028(3) 0.035(3) 0.002(3) -0.006(3) 0.002(3) C2 0.043(4) 0.030(4) 0.029(3) -0.002(2) -0.005(3) 0.007(3) C3 0.043(4) 0.032(4) 0.034(3) -0.003(3) -0.001(3) 0.004(3) C4 0.038(3) 0.032(3) 0.040(3) 0.001(3) -0.003(3) 0.006(3) C5 0.039(4) 0.033(4) 0.040(3) 0.008(3) -0.002(3) 0.005(3) C6 0.038(4) 0.040(5) 0.061(6) 0.004(4) 0.001(4) 0.001(3) C7 0.041(4) 0.048(5) 0.067(7) 0.017(5) 0.006(4) 0.006(4) C8 0.054(5) 0.056(6) 0.044(4) 0.012(4) 0.004(4) 0.004(5) C9 0.048(5) 0.055(5) 0.037(4) 0.002(4) 0.001(3) 0.011(4) N1 0.043(4) 0.036(3) 0.035(3) -0.005(3) 0.002(3) 0.002(3) N2 0.049(4) 0.032(3) 0.027(2) -0.003(2) 0.000(2) 0.005(3) N3 0.052(4) 0.031(3) 0.041(4) 0.001(3) -0.002(3) -0.003(3) O1 0.054(4) 0.039(3) 0.028(2) 0.000(2) 0.003(2) 0.003(3) S1 0.0481(11) 0.0375(10) 0.0383(9) -0.0034(8) -0.0047(8) -0.0039(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 Tl1 O1 2.635(7) . ? Tl1 O1 2.859(7) 1_565 ? Tl1 O1 2.864(8) 3_446 ? C1 N1 1.297(11) . ? C1 C2 1.441(14) . ? C1 S1 1.763(10) . ? C2 N2 1.319(10) . ? C2 C3 1.429(12) . ? C3 N3 1.149(12) . ? C4 C9 1.378(12) . ? C4 N1 1.392(12) . ? C4 C5 1.398(13) . ? C5 C6 1.386(14) . ? C5 S1 1.745(9) . ? C6 C7 1.38(2) . ? C7 C8 1.390(19) . ? C8 C9 1.391(16) . ? N2 O1 1.317(11) . ? 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 107.3(2) . 1_565 ? O1 Tl1 O1 76.2(2) . 3_446 ? O1 Tl1 O1 67.2(3) 1_565 3_446 ? N1 C1 C2 125.4(9) . . ? N1 C1 S1 116.3(8) . . ? C2 C1 S1 118.2(6) . . ? N2 C2 C3 120.8(8) . . ? N2 C2 C1 118.3(8) . . ? C3 C2 C1 120.7(7) . . ? N3 C3 C2 175.0(9) . . ? C9 C4 N1 125.0(9) . . ? C9 C4 C5 119.5(9) . . ? N1 C4 C5 115.4(8) . . ? C6 C5 C4 122.2(9) . . ? C6 C5 S1 128.2(8) . . ? C4 C5 S1 109.6(7) . . ? C7 C6 C5 117.1(11) . . ? C6 C7 C8 121.8(11) . . ? C7 C8 C9 119.9(10) . . ? C4 C9 C8 119.4(10) . . ? C1 N1 C4 110.3(8) . . ? O1 N2 C2 116.6(8) . . ? N2 O1 Tl1 94.2(5) . . ? C5 S1 C1 88.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -163.1(9) . . . . ? S1 C1 C2 N2 13.1(11) . . . . ? N1 C1 C2 C3 12.2(13) . . . . ? S1 C1 C2 C3 -171.6(6) . . . . ? C9 C4 C5 C6 -0.6(14) . . . . ? N1 C4 C5 C6 -178.4(8) . . . . ? C9 C4 C5 S1 178.5(7) . . . . ? N1 C4 C5 S1 0.7(10) . . . . ? C4 C5 C6 C7 0.2(14) . . . . ? S1 C5 C6 C7 -178.7(8) . . . . ? C5 C6 C7 C8 -0.4(16) . . . . ? C6 C7 C8 C9 1.0(17) . . . . ? N1 C4 C9 C8 178.8(9) . . . . ? C5 C4 C9 C8 1.1(14) . . . . ? C7 C8 C9 C4 -1.3(16) . . . . ? C2 C1 N1 C4 176.9(8) . . . . ? S1 C1 N1 C4 0.6(10) . . . . ? C9 C4 N1 C1 -178.6(9) . . . . ? C5 C4 N1 C1 -0.9(11) . . . . ? C3 C2 N2 O1 -1.4(11) . . . . ? C1 C2 N2 O1 173.9(7) . . . . ? C2 N2 O1 Tl1 -164.7(6) . . . . ? O1 Tl1 O1 N2 55.6(6) 1_565 . . . ? O1 Tl1 O1 N2 116.0(5) 3_446 . . . ? C6 C5 S1 C1 178.8(9) . . . . ? C4 C5 S1 C1 -0.3(7) . . . . ? N1 C1 S1 C5 -0.2(7) . . . . ? C2 C1 S1 C5 -176.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 34.78 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 3.949 _refine_diff_density_min -2.528 _refine_diff_density_rms 0.423