# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Dr Ali Morsali' _publ_contact_author_email 'morsali a@yahoo.com' _publ_author_name 'Ali Morsali' # Attachment '- 3-.txt' data_morsali56_0m _database_code_depnum_ccdc_archive 'CCDC 802199' #TrackingRef '- 3-.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 56 _chemical_melting_point ? _chemical_formula_moiety 'C4 H2 N4 Tl1' _chemical_formula_sum 'C4 H2 N4 Tl1' _chemical_formula_weight 310.48 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' 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 24.9570(6) _cell_length_b 3.8807(1) _cell_length_c 12.6821(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.814(1) _cell_angle_gamma 90.00 _cell_volume 1086.36(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2249 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 27.56 _exptl_crystal_description cuboid _exptl_crystal_colour colourless _exptl_crystal_size_min 0.089 _exptl_crystal_size_mid 0.161 _exptl_crystal_size_max 0.233 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.797 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080.0 _exptl_absorpt_coefficient_mu 29.622 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0699 _exptl_absorpt_correction_T_max 0.1512 _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 3609 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.56 _reflns_number_total 1249 _reflns_number_gt 1153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _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^)+(0.0319P)^2^+9.3568P] 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 1249 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0222 _refine_ls_R_factor_gt 0.0205 _refine_ls_wR_factor_ref 0.0641 _refine_ls_wR_factor_gt 0.0632 _refine_ls_goodness_of_fit_ref 1.194 _refine_ls_restrained_S_all 1.194 _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 0.556432(9) 1.01209(4) 0.428479(17) 0.01085(11) Uani 1 1 d . . . C1 C 0.6388(2) 0.5881(14) 0.7925(4) 0.0082(9) Uani 1 1 d . . . C2 C 0.6958(2) 0.6708(12) 0.8996(4) 0.0076(9) Uani 1 1 d . . . C3 C 0.7424(2) 0.8328(13) 0.8870(4) 0.0101(10) Uani 1 1 d . . . H3 H 0.7374 0.8877 0.8099 0.012 Uiso 1 1 calc R . . C4 C 0.7959(2) 0.9130(14) 0.9872(5) 0.0112(10) Uani 1 1 d . . . H4 H 0.8274 1.0266 0.9786 0.013 Uiso 1 1 calc R . . N1 N 0.6269(2) 0.6651(12) 0.6802(4) 0.0131(9) Uani 1 1 d . . . N2 N 0.5697(2) 0.5538(13) 0.6122(5) 0.0150(10) Uani 1 1 d . . . N3 N 0.5481(2) 0.4138(14) 0.6804(4) 0.0137(9) Uani 1 1 d . . . N4 N 0.5909(2) 0.4363(12) 0.7950(4) 0.0124(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Tl1 0.01208(15) 0.01049(15) 0.01214(15) -0.00032(6) 0.00746(11) -0.00028(7) C1 0.006(2) 0.011(2) 0.008(2) -0.001(2) 0.0032(18) 0.003(2) C2 0.006(2) 0.007(2) 0.011(2) -0.0023(17) 0.0042(18) 0.0012(17) C3 0.010(2) 0.014(2) 0.008(2) 0.0005(18) 0.0066(19) 0.0014(19) C4 0.008(2) 0.010(2) 0.018(3) -0.001(2) 0.008(2) -0.002(2) N1 0.011(2) 0.018(2) 0.010(2) -0.0008(17) 0.0053(17) -0.0017(18) N2 0.012(2) 0.022(2) 0.010(2) -0.0017(18) 0.0038(19) -0.0009(19) N3 0.010(2) 0.019(2) 0.013(2) -0.0041(18) 0.0060(19) -0.005(2) N4 0.011(2) 0.015(2) 0.012(2) -0.0002(18) 0.0063(18) -0.0038(18) _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 N2 2.825(5) . ? Tl1 N4 2.827(5) 6_565 ? C1 N4 1.345(7) . ? C1 N1 1.347(6) . ? C1 C2 1.473(7) . ? C2 C4 1.391(7) 7_667 ? C2 C3 1.396(7) . ? C3 C4 1.382(7) . ? C3 H3 0.9500 . ? C4 C2 1.391(7) 7_667 ? C4 H4 0.9500 . ? N1 N2 1.350(7) . ? N2 N3 1.329(7) . ? N3 N4 1.346(6) . ? N4 Tl1 2.827(5) 6_566 ? 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 N2 Tl1 N4 98.93(14) . 6_565 ? N4 C1 N1 111.3(4) . . ? N4 C1 C2 124.1(5) . . ? N1 C1 C2 124.6(5) . . ? C4 C2 C3 119.6(4) 7_667 . ? C4 C2 C1 121.0(5) 7_667 . ? C3 C2 C1 119.4(5) . . ? C4 C3 C2 119.7(5) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.1 . . ? C3 C4 C2 120.7(5) . 7_667 ? C3 C4 H4 119.6 . . ? C2 C4 H4 119.6 7_667 . ? C1 N1 N2 104.4(4) . . ? N3 N2 N1 110.1(4) . . ? N3 N2 Tl1 150.1(4) . . ? N1 N2 Tl1 90.4(3) . . ? N2 N3 N4 108.6(5) . . ? C1 N4 N3 105.6(4) . . ? C1 N4 Tl1 143.6(4) . 6_566 ? N3 N4 Tl1 107.3(3) . 6_566 ? 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 N4 C1 C2 C4 1.4(8) . . . 7_667 ? N1 C1 C2 C4 179.0(5) . . . 7_667 ? N4 C1 C2 C3 -179.2(5) . . . . ? N1 C1 C2 C3 -1.6(8) . . . . ? C4 C2 C3 C4 -1.0(8) 7_667 . . . ? C1 C2 C3 C4 179.6(5) . . . . ? C2 C3 C4 C2 1.0(9) . . . 7_667 ? N4 C1 N1 N2 -0.2(6) . . . . ? C2 C1 N1 N2 -178.1(5) . . . . ? C1 N1 N2 N3 -0.4(6) . . . . ? C1 N1 N2 Tl1 157.4(3) . . . . ? N4 Tl1 N2 N3 -132.4(7) 6_565 . . . ? N4 Tl1 N2 N1 93.0(3) 6_565 . . . ? N1 N2 N3 N4 1.0(6) . . . . ? Tl1 N2 N3 N4 -129.8(6) . . . . ? N1 C1 N4 N3 0.8(6) . . . . ? C2 C1 N4 N3 178.6(5) . . . . ? N1 C1 N4 Tl1 154.8(5) . . . 6_566 ? C2 C1 N4 Tl1 -27.4(9) . . . 6_566 ? N2 N3 N4 C1 -1.1(6) . . . . ? N2 N3 N4 Tl1 -165.2(4) . . . 6_566 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.878 _refine_diff_density_min -1.717 _refine_diff_density_rms 0.289 # Attachment '- 2-new.txt' data_107_0m _database_code_depnum_ccdc_archive 'CCDC 825946' #TrackingRef '- 2-new.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 Br N4 Tl' _chemical_formula_sum 'C7 H4 Br N4 Tl' _chemical_formula_weight 428.42 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' Br Br -0.2901 2.4595 '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 C2/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 36.831(2) _cell_length_b 3.9678(3) _cell_length_c 12.5375(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.589(4) _cell_angle_gamma 90.00 _cell_volume 1755.93(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2010 _cell_measurement_theta_min 3.39 _cell_measurement_theta_max 27.37 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.023 _exptl_crystal_size_mid 0.051 _exptl_crystal_size_max 0.137 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 22.899 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0238 _exptl_absorpt_correction_T_max 0.0644 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7817 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 46 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2008 _reflns_number_gt 1286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Apex2' _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^)+(0.0500P)^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 2008 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 0.033676(8) -0.00483(9) 0.40510(2) 0.02527(12) Uani 1 1 d . . . Br1 Br 0.22625(2) 0.9817(2) 0.62575(7) 0.0327(2) Uani 1 1 d . . . C1 C 0.0867(2) 0.597(2) 0.2436(7) 0.0237(18) Uani 1 1 d . . . C2 C 0.1208(2) 0.683(2) 0.3343(7) 0.0225(17) Uani 1 1 d . . . C3 C 0.1506(2) 0.847(2) 0.3119(7) 0.0244(17) Uani 1 1 d . . . H3 H 0.1496 0.8985 0.2371 0.029 Uiso 1 1 calc R . . C4 C 0.1823(2) 0.9378(19) 0.3986(7) 0.0271(19) Uani 1 1 d . . . H4 H 0.2026 1.0601 0.3839 0.033 Uiso 1 1 calc R . . C5 C 0.1838(2) 0.846(2) 0.5073(7) 0.0290(19) Uani 1 1 d . . . C6 C 0.1543(2) 0.680(2) 0.5306(7) 0.0257(18) Uani 1 1 d . . . H6 H 0.1553 0.6246 0.6052 0.031 Uiso 1 1 calc R . . C7 C 0.1233(2) 0.595(2) 0.4446(7) 0.0285(19) Uani 1 1 d . . . H7 H 0.1031 0.4735 0.4599 0.034 Uiso 1 1 calc R . . N1 N 0.0561(2) 0.4314(17) 0.2609(6) 0.0270(16) Uani 1 1 d . . . N2 N 0.03131(19) 0.411(2) 0.1583(5) 0.0289(18) Uani 1 1 d . . . N3 N 0.0461(2) 0.5632(17) 0.0857(6) 0.0285(17) Uani 1 1 d . . . N4 N 0.0809(2) 0.6732(19) 0.1371(5) 0.0272(16) 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 0.02883(19) 0.02218(19) 0.02540(17) 0.00011(14) 0.00871(12) -0.00011(17) Br1 0.0262(4) 0.0295(5) 0.0359(4) -0.0016(4) -0.0016(3) -0.0015(5) C1 0.024(4) 0.020(4) 0.027(4) -0.004(3) 0.005(3) 0.001(3) C2 0.026(4) 0.015(4) 0.027(4) -0.001(3) 0.009(3) 0.002(3) C3 0.027(4) 0.015(4) 0.031(4) 0.004(3) 0.008(4) 0.005(4) C4 0.026(4) 0.019(5) 0.039(5) 0.003(3) 0.013(4) 0.001(3) C5 0.018(4) 0.034(5) 0.033(5) 0.001(4) 0.005(4) 0.000(4) C6 0.029(5) 0.022(5) 0.029(4) -0.002(3) 0.013(4) -0.006(4) C7 0.024(4) 0.030(5) 0.035(5) -0.001(4) 0.015(4) -0.002(4) N1 0.027(4) 0.028(4) 0.026(3) 0.003(3) 0.007(3) -0.001(3) N2 0.024(4) 0.039(5) 0.023(4) -0.002(3) 0.006(3) -0.002(3) N3 0.028(4) 0.030(5) 0.027(3) -0.002(3) 0.006(3) 0.002(3) N4 0.029(4) 0.029(4) 0.022(3) -0.002(3) 0.004(3) 0.001(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 N1 2.793(7) . ? Tl1 N3 2.796(7) 6_566 ? Tl1 N2 2.827(7) 2 ? Br1 C5 1.902(9) . ? C1 N4 1.325(10) . ? C1 N1 1.375(11) . ? C1 C2 1.473(11) . ? C2 C3 1.371(11) . ? C2 C7 1.405(11) . ? C3 C4 1.398(12) . ? C3 H3 0.9500 . ? C4 C5 1.398(12) . ? C4 H4 0.9500 . ? C5 C6 1.371(11) . ? C6 C7 1.370(12) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? N1 N2 1.351(9) . ? N2 N3 1.332(10) . ? N2 Tl1 2.827(7) 2 ? N3 N4 1.334(10) . ? N3 Tl1 2.796(7) 6_565 ? 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 Tl1 N3 97.2(2) . 6_566 ? N1 Tl1 N2 80.79(19) . 2 ? N3 Tl1 N2 78.0(2) 6_566 2 ? N4 C1 N1 111.4(7) . . ? N4 C1 C2 125.5(8) . . ? N1 C1 C2 123.1(7) . . ? C3 C2 C7 119.3(8) . . ? C3 C2 C1 120.5(7) . . ? C7 C2 C1 120.2(8) . . ? C2 C3 C4 120.2(8) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 118.8(8) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C6 C5 C4 121.5(8) . . ? C6 C5 Br1 119.6(7) . . ? C4 C5 Br1 118.8(6) . . ? C7 C6 C5 118.9(8) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C2 121.3(8) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? N2 N1 C1 103.9(6) . . ? N2 N1 Tl1 109.5(5) . . ? C1 N1 Tl1 143.7(5) . . ? N3 N2 N1 109.0(7) . . ? N3 N2 Tl1 123.5(5) . 2 ? N1 N2 Tl1 126.2(5) . 2 ? N2 N3 N4 110.1(7) . . ? N2 N3 Tl1 146.5(5) . 6_565 ? N4 N3 Tl1 95.7(5) . 6_565 ? C1 N4 N3 105.6(7) . . ? 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 N4 C1 C2 C3 -2.3(13) . . . . ? N1 C1 C2 C3 179.6(8) . . . . ? N4 C1 C2 C7 178.6(8) . . . . ? N1 C1 C2 C7 0.5(12) . . . . ? C7 C2 C3 C4 -2.9(12) . . . . ? C1 C2 C3 C4 178.0(8) . . . . ? C2 C3 C4 C5 2.9(12) . . . . ? C3 C4 C5 C6 -2.4(13) . . . . ? C3 C4 C5 Br1 -178.0(6) . . . . ? C4 C5 C6 C7 1.9(13) . . . . ? Br1 C5 C6 C7 177.6(7) . . . . ? C5 C6 C7 C2 -2.0(13) . . . . ? C3 C2 C7 C6 2.5(12) . . . . ? C1 C2 C7 C6 -178.4(8) . . . . ? N4 C1 N1 N2 0.2(10) . . . . ? C2 C1 N1 N2 178.5(7) . . . . ? N4 C1 N1 Tl1 157.0(6) . . . . ? C2 C1 N1 Tl1 -24.7(14) . . . . ? N3 Tl1 N1 N2 -136.4(5) 6_566 . . . ? N2 Tl1 N1 N2 -59.9(5) 2 . . . ? N3 Tl1 N1 C1 67.5(9) 6_566 . . . ? N2 Tl1 N1 C1 144.0(9) 2 . . . ? C1 N1 N2 N3 -1.6(9) . . . . ? Tl1 N1 N2 N3 -167.3(5) . . . . ? C1 N1 N2 Tl1 165.7(5) . . . 2 ? Tl1 N1 N2 Tl1 0.1(7) . . . 2 ? N1 N2 N3 N4 2.5(10) . . . . ? Tl1 N2 N3 N4 -165.3(5) 2 . . . ? N1 N2 N3 Tl1 -135.4(8) . . . 6_565 ? Tl1 N2 N3 Tl1 56.9(12) 2 . . 6_565 ? N1 C1 N4 N3 1.3(10) . . . . ? C2 C1 N4 N3 -177.0(8) . . . . ? N2 N3 N4 C1 -2.3(9) . . . . ? Tl1 N3 N4 C1 155.8(6) 6_565 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.637 _refine_diff_density_min -1.925 _refine_diff_density_rms 0.227 data_sad _database_code_depnum_ccdc_archive 'CCDC 826764' #TrackingRef '- 1-new.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 N4 Tl ' _chemical_formula_sum 'C7 H5 N4 Tl' _chemical_formula_weight 349.52 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' 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 'C2/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 32.979(2) _cell_length_b 3.8845(2) _cell_length_c 12.5892(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.331(4) _cell_angle_gamma 90.00 _cell_volume 1586.64(17) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4289 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 29.96 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.114 _exptl_crystal_size_max 0.198 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.926 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 20.301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2018 _exptl_absorpt_correction_T_max 0.4357 _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_reflns_number 12978 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1808 _reflns_number_gt 1299 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _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^)+(0.0336P)^2^+7.9586P] 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 1808 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 C1 C 0.4035(2) 0.3951(14) 0.3528(5) 0.0209(13) Uani 1 1 d . . . C2 C 0.3639(2) 0.2723(14) 0.3745(5) 0.0226(13) Uani 1 1 d . . . C3 C 0.3358(2) 0.1304(16) 0.2904(6) 0.0293(15) Uani 1 1 d . . . H3 H 0.3427 0.1121 0.2205 0.035 Uiso 1 1 calc R . . C4 C 0.2978(2) 0.0157(14) 0.3074(7) 0.0345(16) Uani 1 1 d . . . H4 H 0.2789 -0.0838 0.2496 0.041 Uiso 1 1 calc R . . C5 C 0.2871(2) 0.0462(16) 0.4092(7) 0.0377(17) Uani 1 1 d . . . H5 H 0.2610 -0.0308 0.4215 0.045 Uiso 1 1 calc R . . C6 C 0.3152(2) 0.1901(17) 0.4921(6) 0.0363(17) Uani 1 1 d . . . H6 H 0.3080 0.2122 0.5616 0.044 Uiso 1 1 calc R . . C7 C 0.3537(2) 0.3037(15) 0.4760(5) 0.0280(15) Uani 1 1 d . . . H7 H 0.3727 0.4011 0.5339 0.034 Uiso 1 1 calc R . . N1 N 0.41198(17) 0.4504(13) 0.2540(4) 0.0277(12) Uani 1 1 d . . . N2 N 0.45143(18) 0.5619(13) 0.2716(5) 0.0287(12) Uani 1 1 d . . . N3 N 0.46601(19) 0.5721(15) 0.3757(5) 0.0317(13) Uani 1 1 d . . . N4 N 0.43665(18) 0.4664(13) 0.4302(4) 0.0293(12) Uani 1 1 d . . . Tl1 Tl 0.461318(7) 1.00720(5) 0.102581(18) 0.02396(11) 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 0.022(3) 0.013(2) 0.028(3) -0.001(2) 0.005(3) 0.004(2) C2 0.022(3) 0.015(3) 0.030(3) 0.004(2) 0.002(3) 0.004(2) C3 0.029(4) 0.024(3) 0.035(4) -0.002(3) 0.005(3) 0.000(3) C4 0.025(4) 0.020(3) 0.057(4) -0.002(3) 0.000(3) 0.000(3) C5 0.023(4) 0.030(3) 0.061(5) 0.017(3) 0.012(3) 0.006(3) C6 0.037(5) 0.033(4) 0.043(4) 0.013(3) 0.017(4) 0.008(3) C7 0.030(4) 0.023(3) 0.030(3) 0.007(3) 0.004(3) 0.009(3) N1 0.021(3) 0.034(3) 0.030(3) 0.004(2) 0.009(2) 0.000(2) N2 0.024(3) 0.033(3) 0.030(3) 0.004(2) 0.007(2) 0.000(2) N3 0.029(3) 0.033(3) 0.033(3) -0.001(3) 0.005(2) -0.007(2) N4 0.026(3) 0.035(3) 0.027(3) -0.001(2) 0.006(2) -0.005(3) Tl1 0.03000(17) 0.01691(15) 0.02576(14) 0.00084(10) 0.00718(10) 0.00131(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 C1 N1 1.340(8) . ? C1 N4 1.355(8) . ? C1 C2 1.462(8) . ? C2 C7 1.384(9) . ? C2 C3 1.391(9) . ? C3 C4 1.382(10) . ? C3 H3 0.9500 . ? C4 C5 1.394(12) . ? C4 H4 0.9500 . ? C5 C6 1.382(11) . ? C5 H5 0.9500 . ? C6 C7 1.394(9) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? N1 N2 1.351(8) . ? N2 N3 1.314(8) . ? N2 Tl1 2.806(5) . ? N3 N4 1.347(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N4 111.1(6) . . ? N1 C1 C2 124.5(6) . . ? N4 C1 C2 124.4(6) . . ? C7 C2 C3 119.9(6) . . ? C7 C2 C1 121.1(6) . . ? C3 C2 C1 118.9(6) . . ? C4 C3 C2 120.6(7) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.0(7) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 118.9(7) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 121.5(7) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C2 C7 C6 119.0(7) . . ? C2 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C1 N1 N2 104.7(5) . . ? N3 N2 N1 110.0(5) . . ? N3 N2 Tl1 131.8(4) . . ? N1 N2 Tl1 108.2(4) . . ? N2 N3 N4 109.3(6) . . ? N3 N4 C1 104.9(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 N1 C1 C2 C7 -163.3(6) . . . . ? N4 C1 C2 C7 17.0(9) . . . . ? N1 C1 C2 C3 15.0(9) . . . . ? N4 C1 C2 C3 -164.7(6) . . . . ? C7 C2 C3 C4 -0.8(9) . . . . ? C1 C2 C3 C4 -179.1(5) . . . . ? C2 C3 C4 C5 0.9(9) . . . . ? C3 C4 C5 C6 -0.3(9) . . . . ? C4 C5 C6 C7 -0.2(10) . . . . ? C3 C2 C7 C6 0.2(9) . . . . ? C1 C2 C7 C6 178.5(5) . . . . ? C5 C6 C7 C2 0.3(9) . . . . ? N4 C1 N1 N2 -0.5(7) . . . . ? C2 C1 N1 N2 179.8(5) . . . . ? C1 N1 N2 N3 0.2(7) . . . . ? C1 N1 N2 Tl1 -149.9(4) . . . . ? N1 N2 N3 N4 0.2(7) . . . . ? Tl1 N2 N3 N4 140.8(4) . . . . ? N2 N3 N4 C1 -0.5(7) . . . . ? N1 C1 N4 N3 0.6(7) . . . . ? C2 C1 N4 N3 -179.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.726 _refine_diff_density_min -1.465 _refine_diff_density_rms 0.201 # Attachment '- 5.txt' data_k _database_code_depnum_ccdc_archive 'CCDC 843776' #TrackingRef '- 5.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H7 N4 Tl' _chemical_formula_sum 'C8 H7 N4 Tl' _chemical_formula_weight 363.55 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.7767(10) _cell_length_b 8.9439(9) _cell_length_c 20.868(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1824.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3350 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 25.49 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.647 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 17.657 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.0705 _exptl_absorpt_correction_T_max 0.1433 _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 9071 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 25.49 _reflns_number_total 1693 _reflns_number_gt 1434 _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^)+(0.0497P)^2^+0.3594P] 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 1693 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0790 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.44301(2) 0.88158(2) -0.115662(10) 0.03692(14) Uani 1 1 d . . . N1 N 0.2171(5) 0.8136(5) -0.0550(2) 0.0384(11) Uani 1 1 d . . . N2 N 0.1552(6) 0.6975(6) -0.0826(2) 0.0428(12) Uani 1 1 d . . . N3 N 0.0594(5) 0.6484(6) -0.0451(3) 0.0425(14) Uani 1 1 d . . . N4 N 0.0565(4) 0.7314(6) 0.0088(3) 0.0376(12) Uani 1 1 d . . . C1 C 0.1544(6) 0.8316(6) 0.0008(3) 0.0329(13) Uani 1 1 d . . . C2 C 0.1879(7) 0.9534(6) 0.0472(3) 0.0414(15) Uani 1 1 d . . . H2A H 0.1363 1.0419 0.0354 0.050 Uiso 1 1 calc R . . H2B H 0.2842 0.9775 0.0430 0.050 Uiso 1 1 calc R . . C3 C 0.1586(6) 0.9175(6) 0.1161(3) 0.0330(14) Uani 1 1 d . . . C4 C 0.2443(6) 0.8210(7) 0.1494(3) 0.0421(15) Uani 1 1 d . . . H4 H 0.3212 0.7818 0.1292 0.051 Uiso 1 1 calc R . . C5 C 0.2163(8) 0.7831(8) 0.2118(3) 0.0543(18) Uani 1 1 d . . . H5 H 0.2735 0.7171 0.2334 0.065 Uiso 1 1 calc R . . C6 C 0.1041(10) 0.8425(8) 0.2425(4) 0.062(2) Uani 1 1 d . . . H6 H 0.0865 0.8185 0.2850 0.075 Uiso 1 1 calc R . . C7 C 0.0184(9) 0.9370(8) 0.2100(4) 0.059(2) Uani 1 1 d . . . H7 H -0.0580 0.9764 0.2305 0.070 Uiso 1 1 calc R . . C8 C 0.0449(6) 0.9742(7) 0.1466(3) 0.0460(17) Uani 1 1 d . . . H8 H -0.0142 1.0376 0.1247 0.055 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 0.0433(2) 0.0383(2) 0.02909(19) 0.00025(8) 0.00582(9) 0.00727(9) N1 0.041(3) 0.039(3) 0.035(3) 0.000(2) 0.001(2) -0.005(2) N2 0.050(3) 0.043(3) 0.035(3) 0.002(2) -0.007(3) -0.005(2) N3 0.052(4) 0.039(3) 0.037(3) 0.002(2) -0.011(3) -0.011(2) N4 0.038(3) 0.036(3) 0.039(3) -0.001(2) 0.001(2) -0.010(2) C1 0.036(3) 0.028(3) 0.035(3) 0.007(2) -0.001(3) 0.000(2) C2 0.059(4) 0.028(3) 0.037(3) 0.001(3) 0.001(3) -0.011(3) C3 0.038(3) 0.024(3) 0.037(4) -0.005(2) -0.003(3) -0.011(3) C4 0.027(3) 0.047(3) 0.053(4) 0.002(3) -0.008(3) -0.003(3) C5 0.061(5) 0.060(4) 0.041(4) 0.004(3) -0.021(4) -0.001(4) C6 0.100(7) 0.052(4) 0.036(4) -0.013(3) 0.007(4) -0.030(5) C7 0.067(5) 0.045(4) 0.063(5) -0.011(4) 0.025(4) -0.007(4) C8 0.046(4) 0.032(3) 0.060(5) -0.005(3) 0.006(3) 0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Tl1 N1 2.617(5) . ? Tl1 N4 2.689(5) 4_565 ? Tl1 N3 2.805(5) 8_665 ? N1 C1 1.326(7) . ? N1 N2 1.333(6) . ? N2 N3 1.298(7) . ? N3 N4 1.347(8) . ? N3 Tl1 2.805(5) 8_655 ? N4 C1 1.321(7) . ? N4 Tl1 2.689(5) 4_465 ? C1 C2 1.493(8) . ? C2 C3 1.501(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C8 1.378(8) . ? C3 C4 1.389(9) . ? C4 C5 1.374(9) . ? C4 H4 0.9300 . ? C5 C6 1.377(11) . ? C5 H5 0.9300 . ? C6 C7 1.369(12) . ? C6 H6 0.9300 . ? C7 C8 1.388(10) . ? C7 H7 0.9300 . ? C8 H8 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 N1 Tl1 N4 81.92(14) . 4_565 ? N1 Tl1 N3 86.37(14) . 8_665 ? N4 Tl1 N3 83.53(16) 4_565 8_665 ? C1 N1 N2 105.3(5) . . ? C1 N1 Tl1 141.9(4) . . ? N2 N1 Tl1 110.8(3) . . ? N3 N2 N1 109.3(5) . . ? N2 N3 N4 109.4(5) . . ? N2 N3 Tl1 88.7(4) . 8_655 ? N4 N3 Tl1 155.1(4) . 8_655 ? C1 N4 N3 104.7(5) . . ? C1 N4 Tl1 131.1(4) . 4_465 ? N3 N4 Tl1 119.6(4) . 4_465 ? N4 C1 N1 111.3(5) . . ? N4 C1 C2 124.9(5) . . ? N1 C1 C2 123.8(5) . . ? C1 C2 C3 115.0(5) . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C8 C3 C4 118.9(6) . . ? C8 C3 C2 121.2(6) . . ? C4 C3 C2 119.8(6) . . ? C5 C4 C3 120.5(6) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.3(7) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 119.7(7) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 120.3(7) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C3 C8 C7 120.2(6) . . ? C3 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.022 _refine_diff_density_min -2.013 _refine_diff_density_rms 0.177