# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2000 # CCDC Number: 186/1865 data_kcm5 #Structure 6a _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H24 N5 O6 Tl' _chemical_formula_weight 550.74 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.922(2) _cell_length_b 8.500(1) _cell_length_c 19.517(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.41(1) _cell_angle_gamma 90.00 _cell_volume 1915.6 _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.910 _exptl_crystal_density_method ? _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 8.469 _exptl_absorpt_correction_type DIFABS _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 0.382 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1710 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 23.95 _reflns_number_total 1710 _reflns_number_observed 1705 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 5 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0808P)^2^+100.9920P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1705 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_obs 0.0761 _refine_ls_wR_factor_all 0.2024 _refine_ls_wR_factor_obs 0.1972 _refine_ls_goodness_of_fit_all 1.192 _refine_ls_goodness_of_fit_obs 1.192 _refine_ls_restrained_S_all 1.223 _refine_ls_restrained_S_obs 1.192 _refine_ls_shift/esd_max -0.005 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Tl1 Tl 0.58518(10) -0.18960(15) 0.85966(6) 0.0588(5) Uani 1 d . . C1 C 0.3638(28) -0.0725(41) 0.9600(17) 0.067(9) Uani 1 d . . C2 C 0.8500(37) -0.4296(49) 0.9576(17) 0.095(13) Uani 1 d . . H21 H 0.8864(37) -0.4813(49) 0.9244(17) 0.050 Uiso 1 calc R . H22 H 0.8759(37) -0.4802(49) 1.0034(17) 0.050 Uiso 1 calc R . C3 C 0.8789(31) -0.2599(40) 0.9629(19) 0.074(10) Uani 1 d . . H31 H 0.8415(31) -0.2122(40) 0.9966(19) 0.050 Uiso 1 calc R . H32 H 0.9618(31) -0.2491(40) 0.9817(19) 0.050 Uiso 1 calc R . C4 C 0.8919(25) -0.0223(40) 0.9059(17) 0.067(9) Uani 1 d . . H41 H 0.9759(25) -0.0228(40) 0.9195(17) 0.050 Uiso 1 calc R . H42 H 0.8647(25) 0.0382(40) 0.9407(17) 0.050 Uiso 1 calc R . C5 C 0.8504(28) 0.0499(41) 0.8354(18) 0.072(9) Uani 1 d . . H51 H 0.8823(28) 0.1551(41) 0.8366(18) 0.050 Uiso 1 calc R . H52 H 0.8792(28) -0.0110(41) 0.8014(18) 0.050 Uiso 1 calc R . C6 C 0.6875(29) 0.1298(37) 0.7456(17) 0.070(9) Uani 1 d . . H61 H 0.7195(29) 0.0771(37) 0.7106(17) 0.050 Uiso 1 calc R . H62 H 0.7106(29) 0.2395(37) 0.7475(17) 0.050 Uiso 1 calc R . C7 C 0.5608(40) 0.1178(47) 0.7256(20) 0.099(15) Uani 1 d . . H71 H 0.5295(40) 0.1549(47) 0.7640(20) 0.050 Uiso 1 calc R . H72 H 0.5294(40) 0.1824(47) 0.6843(20) 0.050 Uiso 1 calc R . C8 C 0.4060(29) -0.0522(56) 0.6825(20) 0.092(12) Uani 1 d . . H81 H 0.3661(29) -0.0044(56) 0.7149(20) 0.050 Uiso 1 calc R . H82 H 0.3829(29) 0.0027(56) 0.6377(20) 0.050 Uiso 1 calc R . C9 C 0.3728(30) -0.2215(55) 0.6722(23) 0.101(16) Uani 1 d . . H91 H 0.2904(30) -0.2307(55) 0.6509(23) 0.050 Uiso 1 calc R . H92 H 0.4142(30) -0.2708(55) 0.6410(23) 0.050 Uiso 1 calc R . C10 C 0.3695(30) -0.4654(52) 0.7328(25) 0.104(16) Uani 1 d . . H101 H 0.2864(30) -0.4776(52) 0.7155(25) 0.050 Uiso 1 calc R . H102 H 0.4060(30) -0.5177(52) 0.6998(25) 0.050 Uiso 1 calc R . C11 C 0.4097(46) -0.5421(45) 0.8056(29) 0.123(20) Uani 1 d . . H111 H 0.3712(46) -0.4921(45) 0.8381(29) 0.050 Uiso 1 calc R . H112 H 0.3883(46) -0.6525(45) 0.8022(29) 0.050 Uiso 1 calc R . C12 C 0.5652(44) -0.6024(51) 0.8987(26) 0.114(16) Uani 1 d . . H121 H 0.5392(44) -0.7109(51) 0.8960(26) 0.050 Uiso 1 calc R . H122 H 0.5326(44) -0.5483(51) 0.9331(26) 0.050 Uiso 1 calc R . C13 C 0.6921(39) -0.5976(49) 0.9218(19) 0.092(12) Uani 1 d . . H131 H 0.7187(39) -0.6572(49) 0.9652(19) 0.050 Uiso 1 calc R . H132 H 0.7254(39) -0.6437(49) 0.8859(19) 0.050 Uiso 1 calc R . O1 O 0.7274(27) -0.4370(32) 0.9334(14) 0.100(8) Uani 1 d . . O2 O 0.8488(19) -0.1814(35) 0.9035(11) 0.083(7) Uani 1 d . . O3 O 0.7303(18) 0.0588(26) 0.8128(11) 0.071(6) Uani 1 d . . O4 O 0.5305(19) -0.0377(28) 0.7108(11) 0.075(6) Uani 1 d . . O5 O 0.3999(21) -0.2939(38) 0.7364(15) 0.100(9) Uani 1 d . . O6 O 0.5251(24) -0.5290(30) 0.8307(14) 0.088(8) Uani 1 d . . N1 N 0.2536(24) -0.0601(36) 0.9628(14) 0.071(7) Uani 1 d . . N2 N 0.1999(23) -0.1670(43) 0.9189(15) 0.079(9) Uani 1 d . . N3 N 0.2685(32) -0.2406(41) 0.8906(14) 0.089(10) Uani 1 d . . N4 N 0.3754(22) -0.1945(34) 0.9121(14) 0.073(8) Uani 1 d . . N5 N 0.4494(24) 0.0125(36) 1.0041(14) 0.079(8) Uani 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 0.0587(7) 0.0589(7) 0.0588(7) -0.0003(8) 0.0148(5) -0.0006(8) C1 0.059(20) 0.071(21) 0.073(21) -0.018(19) 0.017(17) -0.036(19) C2 0.124(35) 0.103(32) 0.045(18) 0.021(21) -0.003(20) 0.063(30) C3 0.073(23) 0.068(21) 0.070(23) -0.003(18) -0.004(18) 0.020(18) C4 0.035(16) 0.083(24) 0.076(22) -0.021(19) 0.003(15) 0.010(17) C5 0.067(22) 0.065(21) 0.088(25) -0.024(20) 0.029(19) 0.002(19) C6 0.081(25) 0.048(18) 0.076(23) 0.031(16) 0.010(19) 0.014(17) C7 0.145(41) 0.090(30) 0.069(23) 0.034(22) 0.039(25) 0.078(29) C8 0.060(23) 0.139(39) 0.070(23) 0.019(26) 0.002(18) 0.014(26) C9 0.047(20) 0.141(41) 0.098(30) -0.072(31) -0.016(19) 0.000(23) C10 0.052(21) 0.121(37) 0.143(39) -0.072(33) 0.032(24) -0.054(24) C11 0.172(51) 0.053(23) 0.201(53) -0.034(31) 0.156(46) -0.027(29) C12 0.150(46) 0.076(28) 0.137(41) -0.004(29) 0.076(36) -0.037(30) C13 0.128(37) 0.092(31) 0.062(22) 0.035(22) 0.034(23) 0.008(27) O1 0.132(25) 0.068(17) 0.098(19) -0.012(15) 0.025(18) 0.028(18) O2 0.072(14) 0.119(20) 0.044(12) -0.025(15) -0.012(10) -0.016(16) O3 0.071(15) 0.064(13) 0.084(15) -0.004(13) 0.033(12) 0.013(12) O4 0.068(15) 0.072(17) 0.079(15) 0.000(13) 0.011(12) 0.024(13) O5 0.072(16) 0.137(27) 0.090(19) -0.027(20) 0.015(14) -0.027(18) O6 0.091(19) 0.085(18) 0.108(19) 0.014(16) 0.061(16) -0.027(15) N1 0.066(19) 0.077(19) 0.069(17) -0.019(17) 0.017(14) 0.009(16) N2 0.063(17) 0.119(26) 0.063(17) 0.011(19) 0.030(15) 0.026(20) N3 0.106(25) 0.117(26) 0.042(15) -0.032(16) 0.011(16) -0.023(21) N4 0.058(16) 0.077(18) 0.072(16) -0.040(17) -0.005(13) 0.006(16) N5 0.083(21) 0.093(21) 0.067(16) -0.020(16) 0.029(17) 0.001(19) _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 1.33(4) . ? C1 N5 1.37(4) . ? C1 N4 1.43(4) . ? C2 O1 1.42(4) . ? C2 C3 1.48(5) . ? C3 O2 1.31(4) . ? C4 O2 1.44(4) . ? C4 C5 1.47(4) . ? C5 O3 1.39(4) . ? C6 O3 1.42(3) . ? C6 C7 1.47(5) . ? C7 O4 1.38(5) . ? C8 C9 1.49(6) . ? C8 O4 1.45(4) . ? C9 O5 1.36(5) . ? C10 C11 1.53(6) . ? C10 O5 1.50(5) . ? C11 O6 1.35(5) . ? C12 O6 1.44(5) . ? C12 C13 1.47(6) . ? C13 O1 1.43(5) . ? N1 N2 1.30(4) . ? N2 N3 1.26(4) . ? N3 N4 1.30(4) . ? N5 N5 1.27(5) 3_657 ? 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 N5 121.5(31) . . ? N1 C1 N4 109.9(25) . . ? N5 C1 N4 128.2(29) . . ? O1 C2 C3 105.6(29) . . ? O2 C3 C2 115.3(31) . . ? O2 C4 C5 109.0(26) . . ? O3 C5 C4 113.5(27) . . ? O3 C6 C7 109.0(27) . . ? O4 C7 C6 108.7(27) . . ? C9 C8 O4 110.1(32) . . ? O5 C9 C8 108.6(30) . . ? C11 C10 O5 110.8(30) . . ? O6 C11 C10 111.1(29) . . ? O6 C12 C13 110.7(33) . . ? O1 C13 C12 108.4(36) . . ? C2 O1 C13 109.4(30) . . ? C3 O2 C4 115.6(24) . . ? C5 O3 C6 114.9(25) . . ? C7 O4 C8 110.5(30) . . ? C9 O5 C10 113.4(31) . . ? C11 O6 C12 112.1(31) . . ? N2 N1 C1 104.3(26) . . ? N3 N2 N1 111.6(28) . . ? N2 N3 N4 113.5(28) . . ? N3 N4 C1 100.7(24) . . ? N5 N5 C1 114.5(34) 3_657 . ? _refine_diff_density_max 1.822 _refine_diff_density_min -2.319 _refine_diff_density_rms 0.243 data_96kcm2 #(Compound 7) _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H19 N4 O Tl' _chemical_formula_weight 535.76 _chemical_melting_point ? _chemical_compound_source ? 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' 'Tl' 'Tl' -2.8358 9.6688 '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(No.2) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.413(3) _cell_length_b 9.509(3) _cell_length_c 12.148(5) _cell_angle_alpha 81.02(3) _cell_angle_beta 78.17(3) _cell_angle_gamma 85.76(3) _cell_volume 938.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.896 _exptl_crystal_density_method ? _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 8.619 _exptl_absorpt_correction_type DIFABS _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 0.379 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2298 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 22.00 _reflns_number_total 2298 _reflns_number_observed 2078 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 21 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0836P)^2^+15.5963P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0007(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2277 _refine_ls_number_parameters 241 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_obs 0.0342 _refine_ls_wR_factor_all 0.1311 _refine_ls_wR_factor_obs 0.0978 _refine_ls_goodness_of_fit_all 0.919 _refine_ls_goodness_of_fit_obs 0.909 _refine_ls_restrained_S_all 1.153 _refine_ls_restrained_S_obs 0.909 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Tl1 Tl 0.23946(4) 0.04293(4) 0.11924(3) 0.0184(2) Uani 1 d . . N1 N 0.5132(11) 0.0839(9) 0.1579(7) 0.021(2) Uani 1 d . . N2 N 0.6367(12) 0.0642(9) 0.0733(8) 0.030(2) Uani 1 d . . N3 N 0.7775(11) 0.0849(10) 0.0995(7) 0.026(2) Uani 1 d . . N4 N 0.7396(10) 0.1221(9) 0.2057(7) 0.023(2) Uani 1 d . . C1 C 0.5810(14) 0.1205(11) 0.2381(9) 0.022(3) Uani 1 d . . C2 C 0.4927(12) 0.1511(11) 0.3507(8) 0.017(2) Uani 1 d . . C3 C 0.3589(12) 0.0756(12) 0.4071(8) 0.020(2) Uani 1 d . . H3 H 0.3193(12) 0.0083(12) 0.3728(8) 0.024 Uiso 1 calc R . C4 C 0.2851(14) 0.1006(13) 0.5141(10) 0.030(3) Uani 1 d . . H4 H 0.1978(14) 0.0465(13) 0.5529(10) 0.036 Uiso 1 calc R . C5 C 0.3364(14) 0.2045(13) 0.5666(10) 0.029(3) Uani 1 d . . H5 H 0.2833(14) 0.2214(13) 0.6387(10) 0.035 Uiso 1 calc R . C6 C 0.4690(15) 0.2821(13) 0.5084(10) 0.033(3) Uani 1 d . . H6 H 0.5058(15) 0.3517(13) 0.5419(10) 0.040 Uiso 1 calc R . C7 C 0.5484(15) 0.2565(12) 0.3991(10) 0.030(3) Uani 1 d . . H7 H 0.6367(15) 0.3092(12) 0.3599(10) 0.036 Uiso 1 calc R . C8 C 0.2170(13) 0.2486(12) 0.0240(9) 0.023(3) Uani 1 d . . C9 C 0.2900(13) 0.3616(12) 0.0509(10) 0.026(3) Uani 1 d . . H9 H 0.3478(13) 0.3484(12) 0.1095(10) 0.032 Uiso 1 calc R . C10 C 0.2739(14) 0.4967(12) -0.0131(10) 0.027(3) Uani 1 d . . H10 H 0.3192(14) 0.5743(12) 0.0049(10) 0.033 Uiso 1 calc R . C11 C 0.1938(14) 0.5157(12) -0.1005(11) 0.031(3) Uani 1 d . . H11 H 0.1865(14) 0.6052(12) -0.1432(11) 0.037 Uiso 1 calc R . C12 C 0.1217(14) 0.4001(13) -0.1264(10) 0.034(3) Uani 1 d . . H12 H 0.0645(14) 0.4129(13) -0.1854(10) 0.040 Uiso 1 calc R . C13 C 0.1359(14) 0.2681(12) -0.0647(9) 0.026(3) Uani 1 d . . H13 H 0.0900(14) 0.1909(12) -0.0830(9) 0.032 Uiso 1 calc R . C14 C 0.2364(13) -0.1659(11) 0.2121(9) 0.020(2) Uani 1 d . . C15 C 0.3683(14) -0.2579(12) 0.1913(9) 0.027(3) Uani 1 d . . H15 H 0.4575(14) -0.2296(12) 0.1351(9) 0.032 Uiso 1 calc R . C16 C 0.3697(14) -0.3930(12) 0.2538(11) 0.030(3) Uani 1 d . . H16 H 0.4586(14) -0.4558(12) 0.2377(11) 0.036 Uiso 1 calc R . C17 C 0.2394(14) -0.4350(13) 0.3401(10) 0.030(3) Uani 1 d . . H17 H 0.2408(14) -0.5245(13) 0.3836(10) 0.037 Uiso 1 calc R . C18 C 0.1094(13) -0.3419(12) 0.3593(10) 0.027(3) Uani 1 d . . H18 H 0.0207(13) -0.3690(12) 0.4164(10) 0.032 Uiso 1 calc R . C19 C 0.1061(13) -0.2092(12) 0.2966(10) 0.026(3) Uani 1 d . . H19 H 0.0152(13) -0.1480(12) 0.3111(10) 0.031 Uiso 1 calc R . O1 O 0.0161(8) 0.1300(8) 0.2904(6) 0.025(2) Uani 1 d D . H1A H -0.0759(179) 0.0818(220) 0.2781(191) 0.131(85) Uiso 1 d D . C20 C 0.0238(15) 0.2637(14) 0.3276(12) 0.042(3) Uani 1 d . . H20A H -0.0632(67) 0.2736(43) 0.3911(49) 0.062 Uiso 1 calc R . H20B H 0.0139(111) 0.3393(14) 0.2668(26) 0.062 Uiso 1 calc R . H20C H 0.1261(47) 0.2682(41) 0.3501(74) 0.062 Uiso 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 0.0205(3) 0.0168(3) 0.0178(3) -0.0026(2) -0.0038(2) -0.0009(2) N1 0.037(6) 0.017(5) 0.004(4) 0.001(4) 0.010(4) -0.006(4) N2 0.040(6) 0.013(5) 0.028(6) 0.001(4) 0.012(5) 0.000(4) N3 0.026(5) 0.031(5) 0.022(5) -0.006(4) -0.003(4) -0.017(4) N4 0.014(5) 0.027(5) 0.026(5) -0.010(4) 0.004(4) -0.005(4) C1 0.033(7) 0.014(6) 0.023(6) -0.002(5) -0.012(5) 0.005(5) C2 0.017(5) 0.019(6) 0.010(5) 0.003(4) 0.008(4) -0.002(4) C3 0.021(6) 0.032(6) 0.008(5) -0.002(5) -0.011(5) 0.005(5) C4 0.017(6) 0.043(8) 0.029(7) 0.001(6) -0.010(5) 0.010(5) C5 0.025(7) 0.043(7) 0.021(6) -0.008(6) -0.009(5) 0.016(6) C6 0.039(7) 0.034(7) 0.031(7) -0.016(6) -0.014(6) 0.009(6) C7 0.031(7) 0.028(7) 0.031(7) -0.007(5) -0.007(5) 0.001(5) C8 0.024(6) 0.020(6) 0.028(6) -0.003(5) -0.012(5) -0.002(5) C9 0.026(6) 0.022(6) 0.036(7) -0.010(5) -0.015(5) 0.008(5) C10 0.031(7) 0.022(6) 0.032(7) -0.002(5) -0.015(6) -0.001(5) C11 0.025(6) 0.016(6) 0.044(8) 0.005(5) 0.001(6) 0.001(5) C12 0.034(7) 0.037(8) 0.036(7) -0.007(6) -0.023(6) 0.005(6) C13 0.034(7) 0.023(6) 0.022(6) -0.003(5) -0.005(5) 0.000(5) C14 0.020(6) 0.018(6) 0.025(6) -0.006(5) -0.004(5) -0.006(5) C15 0.029(6) 0.022(6) 0.024(6) -0.006(5) 0.008(5) 0.002(5) C16 0.025(6) 0.022(7) 0.052(8) -0.012(6) -0.027(6) 0.019(5) C17 0.033(7) 0.027(7) 0.033(7) 0.002(5) -0.014(6) -0.004(6) C18 0.022(6) 0.035(7) 0.028(6) 0.001(5) -0.019(5) 0.002(5) C19 0.020(6) 0.025(6) 0.032(7) -0.004(5) 0.000(5) 0.001(5) O1 0.011(4) 0.031(4) 0.033(4) -0.005(3) -0.011(3) 0.008(3) C20 0.035(7) 0.042(8) 0.062(9) -0.026(7) -0.039(7) 0.024(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 Tl1 C14 2.124(11) . ? Tl1 C8 2.128(11) . ? Tl1 N1 2.512(9) . ? Tl1 N2 2.680(9) 2_655 ? Tl1 O1 2.691(7) . ? N1 C1 1.326(14) . ? N1 N2 1.328(12) . ? N2 N3 1.323(13) . ? N2 Tl1 2.680(9) 2_655 ? N3 N4 1.360(13) . ? N4 C1 1.312(14) . ? C1 C2 1.477(15) . ? C2 C3 1.379(15) . ? C2 C7 1.39(2) . ? C3 C4 1.37(2) . ? C4 C5 1.39(2) . ? C5 C6 1.39(2) . ? C6 C7 1.41(2) . ? C8 C13 1.37(2) . ? C8 C9 1.39(2) . ? C9 C10 1.41(2) . ? C10 C11 1.35(2) . ? C11 C12 1.40(2) . ? C12 C13 1.37(2) . ? C14 C15 1.37(2) . ? C14 C19 1.38(2) . ? C15 C16 1.39(2) . ? C16 C17 1.39(2) . ? C17 C18 1.36(2) . ? C18 C19 1.37(2) . ? O1 C20 1.424(14) . ? 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 C14 Tl1 C8 173.9(4) . . ? C14 Tl1 N1 92.0(3) . . ? C8 Tl1 N1 94.1(3) . . ? C14 Tl1 N2 89.9(3) . 2_655 ? C8 Tl1 N2 90.1(4) . 2_655 ? N1 Tl1 N2 93.9(3) . 2_655 ? C14 Tl1 O1 89.2(3) . . ? C8 Tl1 O1 88.6(3) . . ? N1 Tl1 O1 106.8(2) . . ? N2 Tl1 O1 159.3(3) 2_655 . ? C1 N1 N2 104.9(9) . . ? C1 N1 Tl1 140.8(7) . . ? N2 N1 Tl1 114.3(7) . . ? N3 N2 N1 111.4(9) . . ? N3 N2 Tl1 96.6(6) . 2_655 ? N1 N2 Tl1 150.5(8) . 2_655 ? N2 N3 N4 105.4(8) . . ? C1 N4 N3 107.4(8) . . ? N4 C1 N1 110.9(10) . . ? N4 C1 C2 123.8(10) . . ? N1 C1 C2 125.3(10) . . ? C3 C2 C7 120.7(10) . . ? C3 C2 C1 120.6(10) . . ? C7 C2 C1 118.7(9) . . ? C4 C3 C2 119.3(11) . . ? C3 C4 C5 122.2(11) . . ? C6 C5 C4 118.1(11) . . ? C5 C6 C7 120.6(11) . . ? C2 C7 C6 118.9(11) . . ? C13 C8 C9 120.6(10) . . ? C13 C8 Tl1 120.4(8) . . ? C9 C8 Tl1 118.9(8) . . ? C8 C9 C10 118.1(10) . . ? C11 C10 C9 121.2(11) . . ? C10 C11 C12 119.7(11) . . ? C13 C12 C11 119.7(11) . . ? C12 C13 C8 120.6(11) . . ? C15 C14 C19 118.9(10) . . ? C15 C14 Tl1 119.8(8) . . ? C19 C14 Tl1 121.2(8) . . ? C14 C15 C16 120.4(10) . . ? C15 C16 C17 120.4(10) . . ? C18 C17 C16 118.3(11) . . ? C17 C18 C19 121.6(11) . . ? C18 C19 C14 120.4(10) . . ? C20 O1 Tl1 121.9(7) . . ? _refine_diff_density_max 1.739 _refine_diff_density_min -2.355 _refine_diff_density_rms 0.203 data_97kcm8 #(compound 11) _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H18 N4 O Tl' _chemical_formula_weight 486.71 _chemical_melting_point ? _chemical_compound_source ? 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' 'Tl' 'Tl' -2.8358 9.6688 '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(no.2) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.596(2) _cell_length_b 9.862(2) _cell_length_c 11.3880(10) _cell_angle_alpha 108.88(2) _cell_angle_beta 97.69(3) _cell_angle_gamma 92.103(12) _cell_volume 797.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.028 _exptl_crystal_density_method ? _exptl_crystal_F_000 462 _exptl_absorpt_coefficient_mu 10.139 _exptl_absorpt_correction_type DIFABS _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 0.651 _exptl_special_details ; ? ; _diffrn_ambient_temperature 396(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2234 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0749 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 24.83 _reflns_number_total 2234 _reflns_number_observed 2067 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0576P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0002(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2234 _refine_ls_number_parameters 148 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_obs 0.0394 _refine_ls_wR_factor_all 0.1065 _refine_ls_wR_factor_obs 0.1061 _refine_ls_goodness_of_fit_all 1.143 _refine_ls_goodness_of_fit_obs 1.187 _refine_ls_restrained_S_all 1.145 _refine_ls_restrained_S_obs 1.188 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Tl1 Tl 0.24453(5) 0.07958(4) 0.40732(3) 0.0119(2) Uani 1 d . . O1 O 0.1256(11) 0.3008(9) 0.2959(7) 0.027(2) Uani 1 d D . H1 H 0.0335(55) 0.2524(9) 0.2919(116) 0.040 Uiso 1 calc RD . N1 N 0.5677(12) 0.0923(9) 0.3748(8) 0.0152(9) Uani 1 d . . N2 N 0.8191(12) 0.1558(9) 0.3276(8) 0.0152(9) Uani 1 d . . N3 N 0.7039(12) 0.0920(9) 0.4654(8) 0.0152(9) Uani 1 d . . N4 N 0.8537(12) 0.1311(9) 0.4377(8) 0.0152(9) Uani 1 d . . C1 C 0.1670(15) -0.0893(12) 0.2341(10) 0.0183(10) Uani 1 d . . C2 C 0.2479(15) -0.2170(11) 0.2190(10) 0.0183(10) Uani 1 d . . H2 H 0.3271(15) -0.2267(11) 0.2849(10) 0.022 Uiso 1 calc R . C3 C 0.2108(14) -0.3303(12) 0.1056(10) 0.0183(10) Uani 1 d . . H3 H 0.2670(14) -0.4146(12) 0.0955(10) 0.022 Uiso 1 calc R . C4 C 0.0902(15) -0.3174(12) 0.0078(10) 0.0183(10) Uani 1 d . . H4 H 0.0637(15) -0.3928(12) -0.0680(10) 0.022 Uiso 1 calc R . C5 C 0.0090(15) -0.1885(12) 0.0254(10) 0.0183(10) Uani 1 d . . H5 H -0.0725(15) -0.1786(12) -0.0393(10) 0.022 Uiso 1 calc R . C6 C 0.0481(15) -0.0768(12) 0.1365(10) 0.0183(10) Uani 1 d . . H6 H -0.0063(15) 0.0083(12) 0.1461(10) 0.022 Uiso 1 calc R . C7 C 0.3031(14) 0.2538(11) 0.5773(10) 0.014(2) Uani 1 d . . C8 C 0.2331(15) 0.2472(12) 0.6843(10) 0.020(3) Uani 1 d . . H8 H 0.1588(15) 0.1681(12) 0.6800(10) 0.024 Uiso 1 calc R . C9 C 0.2775(17) 0.3615(13) 0.7965(11) 0.027(3) Uani 1 d . . H9 H 0.2305(17) 0.3583(13) 0.8669(11) 0.033 Uiso 1 calc R . C10 C 0.3859(16) 0.4757(12) 0.8058(11) 0.022(3) Uani 1 d . . H10 H 0.4160(16) 0.5493(12) 0.8824(11) 0.027 Uiso 1 calc R . C11 C 0.4542(16) 0.4843(13) 0.6990(11) 0.023(3) Uani 1 d . . H11 H 0.5276(16) 0.5644(13) 0.7046(11) 0.028 Uiso 1 calc R . C12 C 0.4120(16) 0.3741(11) 0.5870(10) 0.020(3) Uani 1 d . . H12 H 0.4570(16) 0.3801(11) 0.5166(10) 0.023 Uiso 1 calc R . C13 C 0.6475(14) 0.1328(11) 0.2919(9) 0.0152(9) Uani 1 d . . C14 C 0.5533(16) 0.1377(12) 0.1694(9) 0.020(2) Uani 1 d . . H14A H 0.6150(16) 0.2114(12) 0.1470(9) 0.024 Uiso 1 calc R . H14B H 0.4334(16) 0.1649(12) 0.1797(9) 0.024 Uiso 1 calc R . C15 C 0.5426(15) -0.0031(11) 0.0638(9) 0.015(2) Uani 1 d . . H15A H 0.4742(15) -0.0753(11) 0.0840(9) 0.017 Uiso 1 calc R . H15B H 0.6621(15) -0.0333(11) 0.0574(9) 0.017 Uiso 1 calc R . C16 C 0.0991(18) 0.4513(15) 0.3471(13) 0.039(3) Uani 1 d . . H16A H -0.0263(19) 0.4629(17) 0.3430(77) 0.059 Uiso 1 calc R . H16B H 0.1499(104) 0.5027(21) 0.2994(54) 0.059 Uiso 1 calc R . H16C H 0.1559(104) 0.4885(28) 0.4330(29) 0.059 Uiso 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 0.0112(3) 0.0127(3) 0.0115(3) 0.0039(2) 0.00139(15) 0.0004(2) O1 0.022(5) 0.034(5) 0.023(5) 0.008(4) 0.004(3) 0.002(4) N1 0.017(2) 0.016(2) 0.012(2) 0.004(2) 0.0014(15) 0.000(2) N2 0.017(2) 0.016(2) 0.012(2) 0.004(2) 0.0014(15) 0.000(2) N3 0.017(2) 0.016(2) 0.012(2) 0.004(2) 0.0014(15) 0.000(2) N4 0.017(2) 0.016(2) 0.012(2) 0.004(2) 0.0014(15) 0.000(2) C1 0.019(3) 0.018(2) 0.018(2) 0.005(2) 0.005(2) 0.003(2) C2 0.019(3) 0.018(2) 0.018(2) 0.005(2) 0.005(2) 0.003(2) C3 0.019(3) 0.018(2) 0.018(2) 0.005(2) 0.005(2) 0.003(2) C4 0.019(3) 0.018(2) 0.018(2) 0.005(2) 0.005(2) 0.003(2) C5 0.019(3) 0.018(2) 0.018(2) 0.005(2) 0.005(2) 0.003(2) C6 0.019(3) 0.018(2) 0.018(2) 0.005(2) 0.005(2) 0.003(2) C7 0.012(6) 0.016(6) 0.017(6) 0.007(5) 0.009(4) 0.000(5) C8 0.021(6) 0.020(6) 0.023(7) 0.008(5) 0.012(5) 0.002(5) C9 0.040(8) 0.029(7) 0.016(7) 0.007(5) 0.015(5) 0.014(6) C10 0.025(7) 0.015(6) 0.023(7) 0.002(5) 0.001(5) 0.010(5) C11 0.023(7) 0.020(6) 0.025(7) 0.006(5) 0.005(5) 0.006(5) C12 0.033(7) 0.014(6) 0.015(6) 0.007(5) 0.008(5) 0.012(5) C13 0.017(2) 0.016(2) 0.012(2) 0.004(2) 0.0014(15) 0.000(2) C14 0.026(7) 0.020(6) 0.018(6) 0.008(5) 0.007(5) 0.006(5) C15 0.020(6) 0.015(6) 0.010(6) 0.006(5) 0.001(4) 0.004(5) C16 0.024(8) 0.042(9) 0.052(9) 0.016(7) 0.006(6) -0.002(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 Tl1 C7 2.112(11) . ? Tl1 C1 2.122(11) . ? Tl1 N1 2.535(9) . ? Tl1 N3 2.569(9) 2_656 ? Tl1 N4 3.076(9) 1_455 ? O1 C16 1.44(2) . ? N1 C13 1.341(14) . ? N1 N3 1.361(12) . ? N2 C13 1.301(14) . ? N2 N4 1.346(12) . ? N3 N4 1.299(12) . ? N3 Tl1 2.569(9) 2_656 ? C1 C6 1.38(2) . ? C1 C2 1.39(2) . ? C2 C3 1.393(15) . ? C3 C4 1.387(15) . ? C4 C5 1.40(2) . ? C5 C6 1.370(15) . ? C7 C12 1.39(2) . ? C7 C8 1.412(15) . ? C8 C9 1.39(2) . ? C9 C10 1.34(2) . ? C10 C11 1.41(2) . ? C11 C12 1.37(2) . ? C13 C14 1.496(14) . ? C14 C15 1.506(14) . ? C15 C15 1.53(2) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 Tl1 C1 175.7(4) . . ? C7 Tl1 N1 90.6(3) . . ? C1 Tl1 N1 92.9(4) . . ? C7 Tl1 N3 88.5(3) . 2_656 ? C1 Tl1 N3 93.8(4) . 2_656 ? N1 Tl1 N3 93.1(3) . 2_656 ? C7 Tl1 N4 84.3(3) . 1_455 ? C1 Tl1 N4 91.7(3) . 1_455 ? N1 Tl1 N4 166.9(3) . 1_455 ? N3 Tl1 N4 98.8(2) 2_656 1_455 ? C13 N1 N3 104.3(8) . . ? C13 N1 Tl1 132.0(7) . . ? N3 N1 Tl1 121.9(6) . . ? C13 N2 N4 107.1(9) . . ? N4 N3 N1 109.6(8) . . ? N4 N3 Tl1 110.3(6) . 2_656 ? N1 N3 Tl1 130.7(6) . 2_656 ? N3 N4 N2 108.2(8) . . ? C6 C1 C2 119.3(10) . . ? C6 C1 Tl1 123.7(8) . . ? C2 C1 Tl1 116.9(8) . . ? C1 C2 C3 120.4(10) . . ? C4 C3 C2 120.1(11) . . ? C3 C4 C5 118.6(10) . . ? C6 C5 C4 121.0(10) . . ? C5 C6 C1 120.6(11) . . ? C12 C7 C8 119.1(10) . . ? C12 C7 Tl1 121.3(7) . . ? C8 C7 Tl1 119.6(8) . . ? C9 C8 C7 118.7(10) . . ? C10 C9 C8 121.9(11) . . ? C9 C10 C11 119.8(11) . . ? C12 C11 C10 119.8(11) . . ? C11 C12 C7 120.8(10) . . ? N2 C13 N1 110.9(9) . . ? N2 C13 C14 124.7(10) . . ? N1 C13 C14 124.3(10) . . ? C13 C14 C15 113.4(9) . . ? C14 C15 C15 113.9(11) . 2_655 ? _refine_diff_density_max 1.352 _refine_diff_density_min -1.494 _refine_diff_density_rms 0.304 data_97kcm3 #(Compound 12) _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C46 H46 Cl N8 O4 Tl3' _chemical_formula_weight 1423.47 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 11.041(2) _cell_length_b 17.520(5) _cell_length_c 12.406(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.21(2) _cell_angle_gamma 90.00 _cell_volume 2315.7(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.041 _exptl_crystal_density_method ? _exptl_crystal_F_000 1340 _exptl_absorpt_coefficient_mu 10.521 _exptl_absorpt_correction_type DIFABS _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 0.182 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3751 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0688 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 23.93 _reflns_number_total 3751 _reflns_number_observed 2626 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 5 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1000P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0004(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3746 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1001 _refine_ls_R_factor_obs 0.0563 _refine_ls_wR_factor_all 0.1590 _refine_ls_wR_factor_obs 0.1319 _refine_ls_goodness_of_fit_all 1.111 _refine_ls_goodness_of_fit_obs 1.126 _refine_ls_restrained_S_all 1.119 _refine_ls_restrained_S_obs 1.126 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Tl1 Tl 0.17510(5) 0.09168(3) 0.03973(5) 0.0316(3) Uani 1 d . . Tl2 Tl -0.42331(7) 0.2500 0.04490(7) 0.0334(3) Uani 1 d S . Cl1 Cl 0.1868(6) 0.2500 0.0437(6) 0.054(2) Uani 1 d S . O1 O -0.4828(9) 0.0428(7) -0.1470(9) 0.032(3) Uiso 1 d . . O2 O -0.5609(11) 0.1048(7) 0.0333(11) 0.046(3) Uani 1 d . . N1 N -0.0553(11) 0.1064(8) 0.0514(10) 0.035(3) Uani 1 d . . N2 N -0.1452(10) 0.0710(8) -0.0317(12) 0.041(3) Uani 1 d . . N3 N -0.2522(12) 0.1043(7) -0.0380(13) 0.043(3) Uani 1 d . . N4 N -0.2366(11) 0.1612(7) 0.0373(12) 0.036(3) Uani 1 d . . C1 C -0.1166(11) 0.1637(8) 0.0911(13) 0.027(3) Uani 1 d . . C2 C 0.2515(14) 0.0792(9) 0.2147(14) 0.038(4) Uani 1 d . . C3 C 0.3378(14) 0.1312(12) 0.2763(16) 0.054(5) Uani 1 d . . H3 H 0.3641(14) 0.1719(12) 0.2398(16) 0.064 Uiso 1 calc R . C4 C 0.3838(18) 0.1239(15) 0.3870(18) 0.066(6) Uani 1 d . . H4 H 0.4430(18) 0.1585(15) 0.4263(18) 0.079 Uiso 1 calc R . C5 C 0.3432(23) 0.0649(16) 0.4429(16) 0.075(7) Uani 1 d . . H5 H 0.3742(23) 0.0603(16) 0.5200(16) 0.090 Uiso 1 calc R . C6 C 0.2569(19) 0.0129(13) 0.3849(19) 0.065(5) Uani 1 d . . H6 H 0.2298(19) -0.0271(13) 0.4222(19) 0.078 Uiso 1 calc R . C7 C 0.2114(14) 0.0207(11) 0.2713(13) 0.043(4) Uani 1 d . . H7 H 0.1526(14) -0.0141(11) 0.2318(13) 0.052 Uiso 1 calc R . C8 C 0.1260(12) 0.0860(9) -0.1364(15) 0.038(4) Uani 1 d . . C9 C 0.1706(16) 0.0290(12) -0.1914(15) 0.052(5) Uani 1 d . . H9 H 0.2256(16) -0.0067(12) -0.1496(15) 0.062 Uiso 1 calc R . C10 C 0.1371(21) 0.0226(13) -0.3062(20) 0.066(6) Uani 1 d . . H10 H 0.1665(21) -0.0178(13) -0.3411(20) 0.079 Uiso 1 calc R . C11 C 0.0586(23) 0.0777(14) -0.3686(19) 0.071(7) Uani 1 d . . H11 H 0.0377(23) 0.0754(14) -0.4461(19) 0.086 Uiso 1 calc R . C12 C 0.0110(24) 0.1361(14) -0.3162(18) 0.079(7) Uani 1 d . . H12 H -0.0411(24) 0.1729(14) -0.3586(18) 0.094 Uiso 1 calc R . C13 C 0.0412(18) 0.1396(13) -0.2010(17) 0.062(5) Uani 1 d . . H13 H 0.0059(18) 0.1771(13) -0.1659(17) 0.074 Uiso 1 calc R . C14 C -0.5042(21) 0.2500 -0.1270(17) 0.030(5) Uani 1 d S . C15 C -0.4285(22) 0.2500 -0.2072(18) 0.044(6) Uani 1 d S . H15 H -0.3414(22) 0.2500 -0.1812(18) 0.053 Uiso 1 calc SR . C16 C -0.4822(21) 0.2500 -0.3189(24) 0.061(8) Uani 1 d S . H16 H -0.4310(21) 0.2500 -0.3676(24) 0.073 Uiso 1 calc SR . C17 C -0.6081(28) 0.2500 -0.3612(22) 0.064(8) Uani 1 d S . H17 H -0.6424(28) 0.2500 -0.4381(22) 0.077 Uiso 1 calc SR . C18 C -0.6860(25) 0.2500 -0.2903(22) 0.054(7) Uani 1 d S . H18 H -0.7727(25) 0.2500 -0.3191(22) 0.065 Uiso 1 calc SR . C19 C -0.6327(19) 0.2500 -0.1740(22) 0.039(5) Uani 1 d S . H19 H -0.6858(19) 0.2500 -0.1270(22) 0.046 Uiso 1 calc SR . C20 C -0.3697(18) 0.2500 0.2202(19) 0.036(5) Uani 1 d S . C21 C -0.3435(21) 0.1819(10) 0.2800(18) 0.062(5) Uani 1 d . . H21 H -0.3565(21) 0.1353(10) 0.2428(18) 0.075 Uiso 1 calc R . C22 C -0.2982(22) 0.1841(18) 0.3946(21) 0.088(8) Uani 1 d . . H22 H -0.2840(22) 0.1379(18) 0.4329(21) 0.105 Uiso 1 calc R . C23 C -0.2728(26) 0.2500 0.4552(31) 0.091(14) Uani 1 d S . H23 H -0.2405(26) 0.2500 0.5324(31) 0.110 Uiso 1 calc SR . C24 C -0.0564(12) 0.2106(8) 0.1884(12) 0.027(3) Uani 1 d . . C25 C 0.0065(13) 0.1717(10) 0.2831(15) 0.042(4) Uani 1 d . . H25 H 0.0071(13) 0.1187(10) 0.2820(15) 0.050 Uiso 1 calc R . C26 C 0.0694(14) 0.2097(10) 0.3808(15) 0.042(4) Uani 1 d . . H26 H 0.1103(14) 0.1825(10) 0.4444(15) 0.050 Uiso 1 calc R . C27 C -0.5111(21) 0.0542(12) -0.2265(38) 0.137(17) Uani 1 d . . H27A H -0.5902(134) 0.0296(135) -0.2578(61) 0.206 Uiso 1 calc R . H27B H -0.4503(132) 0.0359(147) -0.2632(55) 0.206 Uiso 1 calc R . H27C H -0.5207(259) 0.1084(16) -0.2368(39) 0.206 Uiso 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 0.0318(3) 0.0310(4) 0.0318(4) -0.0007(3) 0.0082(2) 0.0011(2) Tl2 0.0329(4) 0.0352(5) 0.0329(5) 0.000 0.0102(3) 0.000 Cl1 0.077(4) 0.027(3) 0.061(5) 0.000 0.026(3) 0.000 O2 0.054(6) 0.043(7) 0.048(8) 0.002(6) 0.023(6) -0.002(5) N1 0.037(6) 0.046(8) 0.019(7) -0.011(6) 0.000(5) 0.005(5) N2 0.022(5) 0.047(8) 0.053(9) 0.001(7) 0.006(6) 0.008(5) N3 0.043(7) 0.032(7) 0.056(10) -0.012(7) 0.016(7) -0.001(5) N4 0.034(6) 0.035(7) 0.035(8) -0.007(6) 0.003(5) 0.004(5) C1 0.022(6) 0.023(7) 0.034(9) 0.004(6) 0.004(6) -0.001(5) C2 0.041(8) 0.035(9) 0.040(10) -0.013(8) 0.012(7) 0.004(6) C3 0.029(8) 0.080(13) 0.048(12) -0.022(11) 0.005(8) -0.020(8) C4 0.061(12) 0.089(16) 0.044(13) -0.026(13) 0.004(10) -0.009(11) C5 0.101(16) 0.100(19) 0.013(10) -0.006(11) -0.005(10) 0.028(14) C6 0.074(13) 0.067(14) 0.048(13) 0.001(11) 0.009(10) -0.006(10) C7 0.041(8) 0.062(11) 0.019(8) 0.003(8) -0.007(6) -0.006(7) C8 0.021(6) 0.044(9) 0.046(10) -0.003(8) 0.005(6) -0.010(6) C9 0.048(9) 0.072(13) 0.034(10) -0.016(10) 0.009(8) 0.007(8) C10 0.091(15) 0.053(12) 0.059(15) -0.011(12) 0.031(12) -0.020(11) C11 0.102(16) 0.075(16) 0.044(13) -0.031(13) 0.032(12) -0.047(13) C12 0.111(18) 0.070(16) 0.036(12) 0.027(12) -0.013(11) -0.026(13) C13 0.064(11) 0.071(14) 0.039(11) 0.010(11) -0.007(9) -0.002(10) C14 0.073(14) 0.006(9) 0.013(10) 0.000 0.016(10) 0.000 C15 0.045(13) 0.072(18) 0.012(11) 0.000 0.003(9) 0.000 C16 0.032(12) 0.107(24) 0.044(17) 0.000 0.011(11) 0.000 C17 0.083(20) 0.079(21) 0.016(13) 0.000 -0.014(12) 0.000 C18 0.053(14) 0.082(20) 0.026(14) 0.000 0.007(11) 0.000 C19 0.032(11) 0.036(12) 0.053(16) 0.000 0.020(10) 0.000 C20 0.030(10) 0.054(14) 0.026(12) 0.000 0.013(9) 0.000 C21 0.107(16) 0.027(10) 0.049(13) 0.013(9) 0.014(11) -0.003(9) C22 0.077(15) 0.120(24) 0.050(16) 0.031(16) -0.011(12) 0.011(14) C23 0.033(13) 0.192(46) 0.043(19) 0.000 0.000(12) 0.000 C24 0.027(7) 0.028(7) 0.023(8) 0.008(7) 0.002(6) -0.006(5) C25 0.034(8) 0.045(9) 0.049(11) 0.007(9) 0.016(7) 0.008(7) C26 0.038(8) 0.050(9) 0.032(9) 0.005(8) 0.001(7) 0.005(7) C27 0.071(14) 0.049(13) 0.338(52) 0.116(22) 0.136(24) 0.046(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Tl1 C8 2.11(2) . ? Tl1 C2 2.12(2) . ? Tl1 N1 2.598(12) . ? Tl1 Cl1 2.7767(10) . ? Tl2 C14 2.08(2) . ? Tl2 C20 2.10(2) . ? Tl2 N4 2.605(12) . ? Tl2 N4 2.605(12) 4_565 ? Cl1 Tl1 2.7767(10) 4_565 ? O1 C27 0.97(4) . ? N1 C1 1.37(2) . ? N1 N2 1.38(2) . ? N2 N3 1.30(2) . ? N3 N4 1.35(2) . ? N4 C1 1.32(2) . ? C1 C24 1.47(2) . ? C2 C7 1.38(2) . ? C2 C3 1.39(2) . ? C3 C4 1.34(3) . ? C4 C5 1.38(3) . ? C5 C6 1.38(3) . ? C6 C7 1.37(3) . ? C8 C9 1.37(2) . ? C8 C13 1.42(3) . ? C9 C10 1.38(3) . ? C10 C11 1.39(3) . ? C11 C12 1.39(4) . ? C12 C13 1.38(3) . ? C14 C19 1.39(3) . ? C14 C15 1.46(3) . ? C15 C16 1.36(4) . ? C16 C17 1.35(4) . ? C17 C18 1.38(4) . ? C18 C19 1.41(4) . ? C20 C21 1.40(2) 4_565 ? C20 C21 1.40(2) . ? C21 C22 1.38(3) . ? C22 C23 1.37(3) . ? C23 C22 1.37(3) 4_565 ? C24 C25 1.38(2) . ? C24 C24 1.38(3) 4_565 ? C25 C26 1.40(2) . ? C26 C26 1.41(3) 4_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 C8 Tl1 C2 168.0(6) . . ? C8 Tl1 N1 94.2(5) . . ? C2 Tl1 N1 94.9(5) . . ? C8 Tl1 Cl1 93.7(5) . . ? C2 Tl1 Cl1 94.6(5) . . ? N1 Tl1 Cl1 86.7(3) . . ? C14 Tl2 C20 171.4(8) . . ? C14 Tl2 N4 95.4(6) . . ? C20 Tl2 N4 91.5(5) . . ? C14 Tl2 N4 95.4(6) . 4_565 ? C20 Tl2 N4 91.5(5) . 4_565 ? N4 Tl2 N4 73.4(6) . 4_565 ? Tl1 Cl1 Tl1 174.8(3) . 4_565 ? C1 N1 N2 105.8(11) . . ? C1 N1 Tl1 132.4(9) . . ? N2 N1 Tl1 116.0(9) . . ? N3 N2 N1 107.9(13) . . ? N2 N3 N4 109.9(13) . . ? C1 N4 N3 107.8(12) . . ? C1 N4 Tl2 131.4(10) . . ? N3 N4 Tl2 120.6(9) . . ? N4 C1 N1 108.6(13) . . ? N4 C1 C24 127.8(13) . . ? N1 C1 C24 123.1(11) . . ? C7 C2 C3 118.1(17) . . ? C7 C2 Tl1 120.1(11) . . ? C3 C2 Tl1 121.7(14) . . ? C4 C3 C2 121.4(20) . . ? C3 C4 C5 120.0(19) . . ? C6 C5 C4 120.2(18) . . ? C7 C6 C5 119.2(21) . . ? C6 C7 C2 121.1(17) . . ? C9 C8 C13 118.0(18) . . ? C9 C8 Tl1 121.4(13) . . ? C13 C8 Tl1 120.5(14) . . ? C8 C9 C10 122.7(20) . . ? C9 C10 C11 118.5(21) . . ? C12 C11 C10 120.6(21) . . ? C13 C12 C11 119.9(23) . . ? C12 C13 C8 120.1(23) . . ? C19 C14 C15 114.8(20) . . ? C19 C14 Tl2 123.2(16) . . ? C15 C14 Tl2 122.0(16) . . ? C16 C15 C14 121.5(21) . . ? C17 C16 C15 121.7(25) . . ? C16 C17 C18 120.1(25) . . ? C17 C18 C19 119.3(23) . . ? C14 C19 C18 122.6(21) . . ? C21 C20 C21 117.7(24) 4_565 . ? C21 C20 Tl2 120.9(12) 4_565 . ? C21 C20 Tl2 120.9(12) . . ? C22 C21 C20 119.5(21) . . ? C23 C22 C21 123.9(27) . . ? C22 C23 C22 115.4(33) . 4_565 ? C25 C24 C24 119.6(10) . 4_565 ? C25 C24 C1 116.3(13) . . ? C24 C24 C1 124.0(8) 4_565 . ? C24 C25 C26 122.0(15) . . ? C25 C26 C26 118.4(10) . 4_565 ? _refine_diff_density_max 2.455 _refine_diff_density_min -2.383 _refine_diff_density_rms 0.295