# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_publication_text _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_name 'Frank Wiesbrock' _publ_contact_author_address ;Graz University of Technology Institute for Chemistry and Technology of Materials Stremayrgasse 9 8010 Graz AUSTRIA ; _publ_contact_author_email f.wiesbrock@tugraz.at _publ_contact_author_phone '++43 316 873 32283' _publ_contact_author_fax '++43 316 873 1032283' loop_ _publ_author_name _publ_author_address F.Wiesbrock ;Graz University of Technology Institute for Chemistry and Technology of Materials Stremayrgasse 9 8010 Graz AUSTRIA ; T.Bodner ;Polymer Competence Center Leoben GmbH Rosseggerstrasse 12 8700 Leoben AUSTRIA ; B.Wirnsberger ;Graz University of Technology Institute for Chemistry and Technology of Materials Stremayrgasse 9 8010 Graz AUSTRIA ; J.Albering ;Graz University of Technology Institute for Chemistry and Technology of Materials Stremayrgasse 9 8010 Graz AUSTRIA ; data_ja2010_050_0m _database_code_depnum_ccdc_archive 'CCDC 814691' #TrackingRef '- Tl LGluH_encifered.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration ad _chemical_formula_moiety 'C10 H16 N2 O8 Tl2' _chemical_formula_sum 'C10 H16 N2 O8 Tl2' _chemical_formula_weight 701.01 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 monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_int_tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4286(5) _cell_length_b 5.3264(3) _cell_length_c 15.7265(9) _cell_angle_alpha 90.00 _cell_angle_beta 107.162(2) _cell_angle_gamma 90.00 _cell_volume 754.63(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9984 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 36.475 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.085 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 21.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0834 _exptl_absorpt_correction_T_max 0.3462 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 39491 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 36.00 _reflns_number_total 7161 _reflns_number_gt 6788 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0340P)^2^+1.3819P] 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 0.0057(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.007(7) _refine_ls_number_reflns 7161 _refine_ls_number_parameters 200 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0707 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 0.327400(13) 0.04286(3) -0.082102(7) 0.00966(5) Uani 1 1 d . . . Tl2 Tl 0.182842(12) 0.55402(2) 0.080708(7) 0.00830(4) Uani 1 1 d . . . O1 O 0.4363(3) -0.1659(6) 0.07692(18) 0.0120(6) Uani 1 1 d . . . O2 O 0.4230(3) 0.2515(6) 0.08159(17) 0.0115(6) Uani 1 1 d . . . O3 O 0.8211(3) 0.3222(6) 0.41881(18) 0.0102(5) Uani 1 1 d . . . O4 O 0.7404(3) -0.0746(5) 0.4081(2) 0.0124(5) Uani 1 1 d . . . O5 O 0.1601(3) 0.5197(6) -0.09086(17) 0.0157(5) Uani 1 1 d . . . O6 O -0.0591(3) 0.5837(6) -0.06765(16) 0.0139(5) Uani 1 1 d . . . O7 O -0.2148(3) 0.0220(5) -0.35320(17) 0.0123(4) Uani 1 1 d . . . O8 O -0.3282(3) 0.3727(6) -0.41590(17) 0.0097(5) Uani 1 1 d . . . N1 N 0.5519(3) 0.5052(6) 0.40833(19) 0.0087(5) Uani 1 1 d . . . H1A H 0.5870 0.4927 0.4686 0.010 Uiso 1 1 d R . . H1B H 0.4560 0.5583 0.3925 0.010 Uiso 1 1 d R . . H1C H 0.6079 0.6175 0.3887 0.010 Uiso 1 1 d R . . N2 N -0.0827(3) 0.6083(6) -0.41890(18) 0.0078(5) Uani 1 1 d . . . H2A H -0.1354 0.5826 -0.4768 0.009 Uiso 1 1 d R . . H2B H 0.0078 0.6736 -0.4161 0.009 Uiso 1 1 d R . . H2C H -0.1326 0.7173 -0.3936 0.009 Uiso 1 1 d R . . C1 C 0.7206(4) 0.1566(7) 0.4022(2) 0.0068(6) Uani 1 1 d . . . C2 C 0.5613(3) 0.2550(7) 0.3680(2) 0.0072(5) Uani 1 1 d . . . H2 H 0.4951 0.1381 0.3859 0.009 Uiso 1 1 calc R . . C3 C 0.5105(4) 0.2793(7) 0.2667(2) 0.0103(6) Uani 1 1 d . . . H3A H 0.4130 0.3564 0.2481 0.012 Uiso 1 1 calc R . . H3B H 0.5785 0.3889 0.2485 0.012 Uiso 1 1 calc R . . C4 C 0.5037(4) 0.0277(9) 0.2202(2) 0.0102(6) Uani 1 1 d . . . H4A H 0.6019 -0.0469 0.2385 0.012 Uiso 1 1 calc R . . H4B H 0.4380 -0.0823 0.2403 0.012 Uiso 1 1 calc R . . C5 C 0.4507(3) 0.0377(12) 0.1196(2) 0.0086(5) Uani 1 1 d . . . C6 C -0.2131(4) 0.2430(7) -0.3809(2) 0.0077(5) Uani 1 1 d . . . C7 C -0.0628(3) 0.3636(7) -0.3704(2) 0.0068(5) Uani 1 1 d . . . H7 H -0.0059 0.2519 -0.3976 0.008 Uiso 1 1 calc R . . C8 C 0.0254(4) 0.3978(7) -0.2720(2) 0.0097(6) Uani 1 1 d . . . H8A H 0.0514 0.2335 -0.2454 0.012 Uiso 1 1 calc R . . H8B H 0.1170 0.4855 -0.2686 0.012 Uiso 1 1 calc R . . C9 C -0.0572(3) 0.5424(10) -0.2176(2) 0.0114(6) Uani 1 1 d . . . H9A H -0.0714 0.7140 -0.2391 0.014 Uiso 1 1 calc R . . H9B H -0.1546 0.4680 -0.2274 0.014 Uiso 1 1 calc R . . C10 C 0.0216(4) 0.5463(12) -0.1181(2) 0.0108(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Tl1 0.01147(6) 0.00914(10) 0.00669(6) -0.00002(8) 0.00008(4) 0.00012(9) Tl2 0.01068(6) 0.00800(9) 0.00530(6) -0.00107(7) 0.00091(4) 0.00058(8) O1 0.0160(15) 0.0080(12) 0.0119(13) -0.0024(9) 0.0041(11) 0.0008(9) O2 0.0167(15) 0.0095(12) 0.0071(12) 0.0015(8) 0.0017(11) 0.0014(9) O3 0.0069(10) 0.0093(12) 0.0138(13) -0.0033(9) 0.0023(9) -0.0002(8) O4 0.0128(13) 0.0084(11) 0.0152(13) 0.0021(9) 0.0027(10) 0.0024(9) O5 0.0141(10) 0.0195(14) 0.0102(11) -0.0015(11) -0.0018(8) 0.0028(11) O6 0.0186(11) 0.0167(13) 0.0064(10) 0.0003(10) 0.0037(8) 0.0023(11) O7 0.0153(10) 0.0082(11) 0.0142(11) 0.0022(9) 0.0056(8) -0.0011(9) O8 0.0075(10) 0.0112(12) 0.0109(12) -0.0005(9) 0.0034(9) -0.0005(8) N1 0.0092(10) 0.0104(13) 0.0071(11) -0.0003(10) 0.0036(8) 0.0028(9) N2 0.0081(11) 0.0083(13) 0.0072(12) 0.0005(9) 0.0027(9) -0.0023(8) C1 0.0054(13) 0.0099(13) 0.0046(13) 0.0000(10) 0.0009(11) 0.0022(10) C2 0.0069(12) 0.0080(13) 0.0076(13) 0.0009(11) 0.0035(10) 0.0004(10) C3 0.0141(15) 0.0099(15) 0.0054(13) 0.0014(11) 0.0007(11) 0.0009(12) C4 0.0179(13) 0.0060(14) 0.0040(12) -0.0023(12) -0.0010(10) -0.0065(14) C5 0.0082(10) 0.0097(15) 0.0076(12) 0.0007(15) 0.0018(9) 0.0012(15) C6 0.0097(13) 0.0094(14) 0.0045(13) -0.0031(10) 0.0030(10) -0.0033(10) C7 0.0067(12) 0.0091(14) 0.0051(12) 0.0002(10) 0.0025(10) 0.0000(10) C8 0.0088(13) 0.0141(16) 0.0051(13) 0.0014(11) 0.0005(10) 0.0006(11) C9 0.0135(12) 0.0163(16) 0.0031(11) 0.0031(14) 0.0003(9) -0.0018(18) C10 0.0161(12) 0.0053(13) 0.0086(12) -0.0007(16) 0.0000(10) -0.0038(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 Tl1 O1 2.651(3) . ? Tl1 O1 2.697(3) 2_655 ? Tl1 O2 2.703(3) . ? Tl2 O5 2.649(3) . ? Tl2 O6 2.744(3) . ? Tl2 O6 2.746(3) 2_545 ? Tl2 O2 2.776(3) . ? O1 C5 1.261(6) . ? O1 Tl1 2.697(3) 2_645 ? O2 C5 1.276(7) . ? O3 C1 1.264(4) . ? O4 C1 1.245(4) . ? O5 C10 1.257(4) . ? O6 C10 1.266(4) . ? O6 Tl2 2.746(3) 2 ? O7 C6 1.257(4) . ? O8 C6 1.267(4) . ? N1 C2 1.490(5) . ? N1 H1A 0.9101 . ? N1 H1B 0.9097 . ? N1 H1C 0.9096 . ? N2 C7 1.493(4) . ? N2 H2A 0.9101 . ? N2 H2B 0.9097 . ? N2 H2C 0.9096 . ? C1 C2 1.531(5) . ? C2 C3 1.528(5) . ? C2 H2 0.9800 . ? C3 C4 1.519(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.513(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 C7 1.521(4) . ? C7 C8 1.537(5) . ? C7 H7 0.9800 . ? C8 C9 1.524(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.522(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? 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 97.25(7) . 2_655 ? O1 Tl1 O2 49.19(8) . . ? O1 Tl1 O2 72.20(9) 2_655 . ? O5 Tl2 O6 48.76(8) . . ? O5 Tl2 O6 87.48(9) . 2_545 ? O6 Tl2 O6 76.15(7) . 2_545 ? O5 Tl2 O2 77.62(8) . . ? O6 Tl2 O2 120.65(8) . . ? O6 Tl2 O2 78.39(9) 2_545 . ? C5 O1 Tl1 95.3(3) . . ? C5 O1 Tl1 121.3(2) . 2_645 ? Tl1 O1 Tl1 110.87(11) . 2_645 ? C5 O2 Tl1 92.5(2) . . ? C5 O2 Tl2 125.1(2) . . ? Tl1 O2 Tl2 101.05(8) . . ? C10 O5 Tl2 95.9(2) . . ? C10 O6 Tl2 91.2(2) . . ? C10 O6 Tl2 114.7(3) . 2 ? Tl2 O6 Tl2 110.14(10) . 2 ? C2 N1 H1A 109.2 . . ? C2 N1 H1B 109.9 . . ? H1A N1 H1B 109.5 . . ? C2 N1 H1C 109.3 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.4 . . ? C7 N2 H2A 109.2 . . ? C7 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C7 N2 H2C 109.7 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.4 . . ? O4 C1 O3 126.0(4) . . ? O4 C1 C2 118.4(3) . . ? O3 C1 C2 115.6(3) . . ? N1 C2 C3 109.2(3) . . ? N1 C2 C1 109.4(3) . . ? C3 C2 C1 111.6(3) . . ? N1 C2 H2 108.9 . . ? C3 C2 H2 108.9 . . ? C1 C2 H2 108.9 . . ? C4 C3 C2 112.5(3) . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 115.2(4) . . ? C5 C4 H4A 108.5 . . ? C3 C4 H4A 108.5 . . ? C5 C4 H4B 108.5 . . ? C3 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? O1 C5 O2 122.9(3) . . ? O1 C5 C4 118.4(5) . . ? O2 C5 C4 118.7(5) . . ? O7 C6 O8 124.4(3) . . ? O7 C6 C7 117.7(3) . . ? O8 C6 C7 117.9(3) . . ? N2 C7 C6 109.9(3) . . ? N2 C7 C8 111.1(3) . . ? C6 C7 C8 111.7(3) . . ? N2 C7 H7 108.0 . . ? C6 C7 H7 108.0 . . ? C8 C7 H7 108.0 . . ? C9 C8 C7 114.3(3) . . ? C9 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? C9 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C10 C9 C8 114.1(3) . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? O5 C10 O6 124.1(3) . . ? O5 C10 C9 119.4(3) . . ? O6 C10 C9 116.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Tl1 O1 C5 60.84(18) 2_655 . . . ? O2 Tl1 O1 C5 1.98(18) . . . . ? O1 Tl1 O1 Tl1 -65.59(16) 2_655 . . 2_645 ? O2 Tl1 O1 Tl1 -124.46(16) . . . 2_645 ? O1 Tl1 O2 C5 -1.95(17) . . . . ? O1 Tl1 O2 C5 -118.8(2) 2_655 . . . ? O1 Tl1 O2 Tl2 -128.42(15) . . . . ? O1 Tl1 O2 Tl2 114.69(10) 2_655 . . . ? O5 Tl2 O2 C5 -127.1(3) . . . . ? O6 Tl2 O2 C5 -103.2(3) . . . . ? O6 Tl2 O2 C5 -37.1(3) 2_545 . . . ? O5 Tl2 O2 Tl1 -26.03(10) . . . . ? O6 Tl2 O2 Tl1 -2.15(14) . . . . ? O6 Tl2 O2 Tl1 63.92(9) 2_545 . . . ? O6 Tl2 O5 C10 -1.0(3) . . . . ? O6 Tl2 O5 C10 72.8(3) 2_545 . . . ? O2 Tl2 O5 C10 151.4(3) . . . . ? O5 Tl2 O6 C10 0.9(3) . . . . ? O6 Tl2 O6 C10 -98.0(3) 2_545 . . . ? O2 Tl2 O6 C10 -30.8(3) . . . . ? O5 Tl2 O6 Tl2 -115.96(14) . . . 2 ? O6 Tl2 O6 Tl2 145.08(14) 2_545 . . 2 ? O2 Tl2 O6 Tl2 -147.68(9) . . . 2 ? O4 C1 C2 N1 150.4(3) . . . . ? O3 C1 C2 N1 -32.1(4) . . . . ? O4 C1 C2 C3 -88.7(4) . . . . ? O3 C1 C2 C3 88.8(4) . . . . ? N1 C2 C3 C4 -174.9(3) . . . . ? C1 C2 C3 C4 64.0(4) . . . . ? C2 C3 C4 C5 178.7(3) . . . . ? Tl1 O1 C5 O2 -3.8(3) . . . . ? Tl1 O1 C5 O2 114.6(3) 2_645 . . . ? Tl1 O1 C5 C4 176.3(2) . . . . ? Tl1 O1 C5 C4 -65.3(4) 2_645 . . . ? Tl1 O2 C5 O1 3.7(3) . . . . ? Tl2 O2 C5 O1 109.1(3) . . . . ? Tl1 O2 C5 C4 -176.4(2) . . . . ? Tl2 O2 C5 C4 -71.1(4) . . . . ? C3 C4 C5 O1 -176.9(3) . . . . ? C3 C4 C5 O2 3.2(4) . . . . ? O7 C6 C7 N2 171.5(3) . . . . ? O8 C6 C7 N2 -9.3(4) . . . . ? O7 C6 C7 C8 -64.7(4) . . . . ? O8 C6 C7 C8 114.5(3) . . . . ? N2 C7 C8 C9 68.6(4) . . . . ? C6 C7 C8 C9 -54.5(4) . . . . ? C7 C8 C9 C10 172.3(4) . . . . ? Tl2 O5 C10 O6 1.9(6) . . . . ? Tl2 O5 C10 C9 179.9(5) . . . . ? Tl2 O6 C10 O5 -1.8(6) . . . . ? Tl2 O6 C10 O5 111.1(5) 2 . . . ? Tl2 O6 C10 C9 -179.9(4) . . . . ? Tl2 O6 C10 C9 -67.0(5) 2 . . . ? C8 C9 C10 O5 25.3(7) . . . . ? C8 C9 C10 O6 -156.5(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 36.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 3.455 _refine_diff_density_min -1.395 _refine_diff_density_rms 0.236