# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Richard Oakley' _publ_contact_author_email OAKLEY@UWATERLOO.CA _publ_section_title ; Self-association of the N-methyl benzotellurodiazolylium cation: implications for the generation of super-heavy atom radicals ; loop_ _publ_author_name 'Richard Oakley' 'Risto Laitinen' 'Raija Oilunkaniemi' 'Robert W Reed' 'Maarit Risto' ; C.M.Robertson ; # Attachment '1OTf_s.cif' data_mebn2sotf_0m _database_code_depnum_ccdc_archive 'CCDC 680269' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 F3 N2 O3 S2' _chemical_formula_weight 300.28 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.495(2) _cell_length_b 11.427(4) _cell_length_c 16.481(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.424(7) _cell_angle_gamma 90.00 _cell_volume 1206.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2252 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 25.19 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_max 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.48 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8958 _exptl_absorpt_correction_T_max 0.9546 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10772 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2629 _reflns_number_gt 2048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II' _computing_cell_refinement 'APEX II' _computing_data_reduction 'APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.3804P] 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 2629 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1' S 0.75018(9) 0.16647(5) 0.66104(4) 0.04660(19) Uani 1 1 d . . . S1 S 0.77132(10) 0.63344(6) 0.31149(4) 0.0531(2) Uani 1 1 d . . . O3' O 0.8201(3) 0.28022(16) 0.64073(12) 0.0622(5) Uani 1 1 d . . . O2' O 0.8506(3) 0.1216(2) 0.73866(12) 0.0758(6) Uani 1 1 d . . . N2 N 0.8277(3) 0.55523(19) 0.39134(12) 0.0521(5) Uani 1 1 d . . . C2 C 0.6683(4) 0.4814(2) 0.39775(14) 0.0454(5) Uani 1 1 d . . . C1 C 0.4956(4) 0.49383(19) 0.33308(14) 0.0433(5) Uani 1 1 d . . . O1' O 0.5291(3) 0.15226(17) 0.64538(14) 0.0707(6) Uani 1 1 d . . . N1 N 0.5371(3) 0.57696(17) 0.28002(11) 0.0463(5) Uani 1 1 d . . . C3 C 0.6616(4) 0.3993(2) 0.46109(16) 0.0562(6) Uani 1 1 d . . . H3A H 0.7745 0.3889 0.5031 0.067 Uiso 1 1 calc R . . C7 C 0.3998(4) 0.6131(2) 0.20355(16) 0.0595(7) Uani 1 1 d . . . H7A H 0.2725 0.5690 0.1973 0.089 Uiso 0.50 1 calc PR . . H7B H 0.4691 0.5988 0.1573 0.089 Uiso 0.50 1 calc PR . . H7C H 0.3688 0.6950 0.2064 0.089 Uiso 0.50 1 calc PR . . H7E H 0.4678 0.6729 0.1767 0.089 Uiso 0.50 1 calc PR . . H7D H 0.2711 0.6430 0.2167 0.089 Uiso 0.50 1 calc PR . . H7F H 0.3715 0.5469 0.1676 0.089 Uiso 0.50 1 calc PR . . C5 C 0.3105(5) 0.3508(2) 0.39358(19) 0.0636(7) Uani 1 1 d . . . H5A H 0.1912 0.3063 0.3946 0.076 Uiso 1 1 calc R . . C6 C 0.3128(4) 0.4273(2) 0.33058(17) 0.0538(6) Uani 1 1 d . . . H6A H 0.1999 0.4351 0.2883 0.065 Uiso 1 1 calc R . . C4 C 0.4842(5) 0.3360(2) 0.45843(18) 0.0615(7) Uani 1 1 d . . . H4A H 0.4750 0.2817 0.4997 0.074 Uiso 1 1 calc R . . F3' F 0.7594(4) 0.0966(2) 0.51095(12) 0.1185(9) Uani 1 1 d . . . F2' F 0.8027(5) -0.03958(18) 0.60013(17) 0.1304(10) Uani 1 1 d . . . F1' F 1.0487(4) 0.0804(2) 0.59168(16) 0.1180(8) Uani 1 1 d . . . C1' C 0.8423(5) 0.0717(3) 0.5864(2) 0.0729(8) 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 S1' 0.0406(3) 0.0459(3) 0.0529(3) 0.0063(2) 0.0065(2) 0.0017(2) S1 0.0509(4) 0.0505(4) 0.0564(4) -0.0007(3) 0.0043(3) -0.0034(3) O3' 0.0701(12) 0.0508(10) 0.0659(11) 0.0055(9) 0.0114(9) -0.0098(9) O2' 0.0734(14) 0.0889(15) 0.0635(12) 0.0257(11) 0.0063(10) 0.0131(11) N2 0.0462(11) 0.0560(12) 0.0521(11) -0.0065(9) 0.0017(9) -0.0016(9) C2 0.0458(13) 0.0462(13) 0.0432(12) -0.0048(10) 0.0042(9) 0.0058(10) C1 0.0435(12) 0.0399(11) 0.0456(12) -0.0044(9) 0.0051(9) 0.0062(9) O1' 0.0404(10) 0.0673(13) 0.1037(16) -0.0025(11) 0.0099(10) -0.0009(9) N1 0.0463(11) 0.0435(11) 0.0466(10) -0.0013(8) 0.0004(8) 0.0056(8) C3 0.0629(17) 0.0559(15) 0.0481(13) 0.0016(11) 0.0043(11) 0.0083(13) C7 0.0643(17) 0.0576(15) 0.0518(14) 0.0027(12) -0.0052(12) 0.0130(13) C5 0.0577(17) 0.0525(16) 0.084(2) -0.0045(13) 0.0211(15) -0.0039(12) C6 0.0431(13) 0.0518(14) 0.0644(15) -0.0060(12) 0.0023(11) 0.0003(11) C4 0.0737(19) 0.0515(15) 0.0614(16) 0.0074(12) 0.0168(14) 0.0056(13) F3' 0.156(2) 0.128(2) 0.0669(12) -0.0269(12) 0.0036(13) 0.0497(17) F2' 0.178(3) 0.0532(12) 0.171(2) -0.0180(13) 0.060(2) 0.0166(14) F1' 0.0795(14) 0.146(2) 0.1380(19) -0.0164(16) 0.0452(13) 0.0330(14) C1' 0.076(2) 0.0617(19) 0.082(2) -0.0023(15) 0.0171(17) 0.0195(15) _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 S1' O1' 1.4262(19) . ? S1' O2' 1.432(2) . ? S1' O3' 1.4343(19) . ? S1' C1' 1.812(3) . ? S1 N2 1.583(2) . ? S1 N1 1.656(2) . ? N2 C2 1.353(3) . ? C2 C3 1.409(3) . ? C2 C1 1.422(3) . ? C1 N1 1.348(3) . ? C1 C6 1.404(3) . ? N1 C7 1.478(3) . ? C3 C4 1.355(4) . ? C5 C6 1.359(4) . ? C5 C4 1.431(4) . ? F3' C1' 1.304(4) . ? F2' C1' 1.324(4) . ? F1' C1' 1.333(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1' S1' O2' 114.75(13) . . ? O1' S1' O3' 114.13(12) . . ? O2' S1' O3' 114.69(13) . . ? O1' S1' C1' 104.10(15) . . ? O2' S1' C1' 103.85(14) . . ? O3' S1' C1' 103.36(14) . . ? N2 S1 N1 96.66(11) . . ? C2 N2 S1 109.94(16) . . ? N2 C2 C3 126.1(2) . . ? N2 C2 C1 113.5(2) . . ? C3 C2 C1 120.3(2) . . ? N1 C1 C6 128.3(2) . . ? N1 C1 C2 109.9(2) . . ? C6 C1 C2 121.8(2) . . ? C1 N1 C7 126.4(2) . . ? C1 N1 S1 110.03(15) . . ? C7 N1 S1 123.56(18) . . ? C4 C3 C2 117.4(2) . . ? C6 C5 C4 122.7(3) . . ? C5 C6 C1 116.1(2) . . ? C3 C4 C5 121.6(3) . . ? F3' C1' F2' 108.2(3) . . ? F3' C1' F1' 107.4(3) . . ? F2' C1' F1' 106.4(3) . . ? F3' C1' S1' 112.7(2) . . ? F2' C1' S1' 111.3(2) . . ? F1' C1' S1' 110.6(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.269 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.050 # Attachment '1OTf_se.cif' data_mebsen2otf_0m _database_code_depnum_ccdc_archive 'CCDC 680270' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'N-methylbenzylselanadiazolium OTf' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 F3 N2 O3 S Se' _chemical_formula_weight 347.18 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.403(2) _cell_length_b 8.5474(19) _cell_length_c 16.738(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.910(4) _cell_angle_gamma 90.00 _cell_volume 1195.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1594 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 26.13 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_max 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.928 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.355 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.58 _exptl_absorpt_correction_T_max 0.85 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4636 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 26.29 _reflns_number_total 2400 _reflns_number_gt 1871 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II' _computing_cell_refinement 'APEX II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0659P)^2^+3.6863P] 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 2400 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1536 _refine_ls_wR_factor_gt 0.1437 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 Se1 Se 0.39975(7) 1.00933(7) 0.39854(3) 0.0441(2) Uani 1 1 d . . . N1 N 0.2090(5) 1.0860(6) 0.3531(3) 0.0404(11) Uani 1 1 d . . . N2 N 0.3470(6) 1.0631(6) 0.4941(3) 0.0420(11) Uani 1 1 d . . . C6 C -0.0268(7) 1.2198(8) 0.3951(4) 0.0505(15) Uani 1 1 d . . . H6A H -0.0792 1.2312 0.3437 0.061 Uiso 1 1 calc R . . C2 C 0.2036(7) 1.1301(7) 0.4878(3) 0.0395(13) Uani 1 1 d . . . C1 C 0.1229(7) 1.1464(7) 0.4083(3) 0.0383(13) Uani 1 1 d . . . C4 C -0.0157(9) 1.2547(10) 0.5403(5) 0.067(2) Uani 1 1 d . . . H4A H -0.0668 1.2912 0.5833 0.080 Uiso 1 1 calc R . . C3 C 0.1285(8) 1.1855(9) 0.5549(4) 0.0549(17) Uani 1 1 d . . . H3A H 0.1772 1.1743 0.6071 0.066 Uiso 1 1 calc R . . C7 C 0.1599(9) 1.0805(9) 0.2659(4) 0.0575(18) Uani 1 1 d . . . H7A H 0.0560 1.1270 0.2549 0.086 Uiso 0.50 1 calc PR . . H7B H 0.1561 0.9736 0.2482 0.086 Uiso 0.50 1 calc PR . . H7C H 0.2358 1.1373 0.2380 0.086 Uiso 0.50 1 calc PR . . H7D H 0.2426 1.0316 0.2392 0.086 Uiso 0.50 1 calc PR . . H7E H 0.1425 1.1850 0.2459 0.086 Uiso 0.50 1 calc PR . . H7F H 0.0628 1.0213 0.2561 0.086 Uiso 0.50 1 calc PR . . C5 C -0.0922(8) 1.2738(10) 0.4612(5) 0.066(2) Uani 1 1 d . . . H5A H -0.1903 1.3249 0.4542 0.079 Uiso 1 1 calc R . . C1' C 0.4220(10) 0.5176(9) 0.3801(5) 0.063(2) Uani 1 1 d . . . F1' F 0.3093(11) 0.4836(10) 0.4280(5) 0.161(4) Uani 1 1 d . . . F2' F 0.5047(7) 0.3931(7) 0.3812(4) 0.108(2) Uani 1 1 d . . . F3' F 0.4972(11) 0.6226(7) 0.4182(4) 0.172(4) Uani 1 1 d . . . S1' S 0.3276(2) 0.5746(2) 0.28361(9) 0.0536(5) Uani 1 1 d . . . O1' O 0.2321(12) 0.4477(9) 0.2583(7) 0.165(5) Uani 1 1 d . . . O2' O 0.2429(7) 0.7147(6) 0.2969(3) 0.0711(15) Uani 1 1 d . . . O3' O 0.4605(11) 0.5957(16) 0.2413(5) 0.188(6) 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 Se1 0.0448(4) 0.0498(4) 0.0377(3) -0.0050(3) 0.0036(2) 0.0102(3) N1 0.040(3) 0.044(3) 0.036(2) -0.003(2) 0.000(2) 0.001(2) N2 0.043(3) 0.048(3) 0.034(2) 0.000(2) -0.001(2) 0.004(2) C6 0.043(3) 0.052(4) 0.055(4) 0.002(3) 0.000(3) 0.005(3) C2 0.041(3) 0.045(3) 0.034(3) 0.003(2) 0.008(2) 0.003(3) C1 0.041(3) 0.037(3) 0.037(3) 0.001(2) 0.006(2) -0.001(2) C4 0.058(4) 0.088(6) 0.058(4) 0.001(4) 0.026(3) 0.022(4) C3 0.058(4) 0.069(5) 0.039(3) -0.005(3) 0.013(3) 0.006(3) C7 0.061(4) 0.074(5) 0.035(3) -0.005(3) -0.003(3) 0.006(4) C5 0.041(4) 0.082(6) 0.075(5) -0.003(4) 0.011(3) 0.018(4) C1' 0.081(5) 0.057(5) 0.050(4) -0.002(3) 0.000(4) 0.019(4) F1' 0.183(8) 0.204(9) 0.105(5) 0.072(5) 0.061(5) 0.060(6) F2' 0.126(5) 0.087(4) 0.104(4) 0.000(3) -0.029(3) 0.047(4) F3' 0.267(9) 0.062(3) 0.152(6) -0.001(4) -0.148(7) -0.011(5) S1' 0.0620(10) 0.0609(11) 0.0367(8) -0.0061(7) -0.0006(7) 0.0137(9) O1' 0.176(9) 0.073(5) 0.216(10) -0.030(6) -0.123(8) 0.008(5) O2' 0.087(4) 0.057(3) 0.064(3) -0.005(3) -0.015(3) 0.021(3) O3' 0.160(8) 0.309(14) 0.112(6) 0.093(8) 0.095(6) 0.107(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 N2 1.765(5) . ? Se1 N1 1.824(5) . ? N1 C1 1.334(7) . ? N1 C7 1.475(7) . ? N2 C2 1.328(7) . ? C6 C5 1.365(10) . ? C6 C1 1.402(8) . ? C2 C3 1.426(8) . ? C2 C1 1.438(8) . ? C4 C3 1.348(10) . ? C4 C5 1.419(11) . ? C1' F3' 1.236(9) . ? C1' F2' 1.270(8) . ? C1' F1' 1.333(11) . ? C1' S1' 1.793(8) . ? S1' O1' 1.389(8) . ? S1' O3' 1.394(8) . ? S1' O2' 1.421(5) . ? 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 Se1 N1 89.6(2) . . ? C1 N1 C7 125.5(5) . . ? C1 N1 Se1 111.5(4) . . ? C7 N1 Se1 123.0(4) . . ? C2 N2 Se1 110.5(4) . . ? C5 C6 C1 117.0(6) . . ? N2 C2 C3 123.5(5) . . ? N2 C2 C1 117.0(5) . . ? C3 C2 C1 119.5(5) . . ? N1 C1 C6 127.3(5) . . ? N1 C1 C2 111.4(5) . . ? C6 C1 C2 121.3(5) . . ? C3 C4 C5 122.1(6) . . ? C4 C3 C2 117.7(6) . . ? C6 C5 C4 122.4(6) . . ? F3' C1' F2' 110.5(8) . . ? F3' C1' F1' 101.9(9) . . ? F2' C1' F1' 103.3(7) . . ? F3' C1' S1' 115.0(6) . . ? F2' C1' S1' 115.6(6) . . ? F1' C1' S1' 108.9(7) . . ? O1' S1' O3' 114.4(8) . . ? O1' S1' O2' 115.0(5) . . ? O3' S1' O2' 114.3(6) . . ? O1' S1' C1' 104.5(5) . . ? O3' S1' C1' 100.9(5) . . ? O2' S1' C1' 105.7(3) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.29 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.004 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.108 # Attachment '1OTf_te.cif' data_mr67b_0m _database_code_depnum_ccdc_archive 'CCDC 680271' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 N4 Te2, 2(C F3 O3 S)' _chemical_formula_sum 'C16 H14 F6 N4 O6 S2 Te2' _chemical_formula_weight 791.65 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8089(5) _cell_length_b 8.1785(7) _cell_length_c 11.3633(9) _cell_angle_alpha 100.884(2) _cell_angle_beta 95.645(2) _cell_angle_gamma 106.4140(10) _cell_volume 588.29(8) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2107 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 25.96 _exptl_crystal_description Plate _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.012 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 2.747 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.725 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details 'APEX II' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5172 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 26.34 _reflns_number_total 2379 _reflns_number_gt 2133 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II' _computing_cell_refinement 'APEX II' _computing_data_reduction 'APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0288P)^2^+0.6372P] 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 2379 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0702 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Te Te 0.65608(4) 0.52408(4) 0.38149(3) 0.03714(11) Uani 1 1 d . . . N2 N 0.4498(5) 0.6206(4) 0.4579(3) 0.0346(8) Uani 1 1 d . . . N1 N 0.6291(5) 0.7021(5) 0.2753(3) 0.0371(8) Uani 1 1 d . . . C2 C 0.3982(6) 0.7400(5) 0.4095(4) 0.0319(9) Uani 1 1 d . . . C3 C 0.2563(7) 0.8266(5) 0.4530(4) 0.0390(10) Uani 1 1 d . . . H3A H 0.1933 0.8005 0.5191 0.047 Uiso 1 1 calc R . . C4 C 0.2148(7) 0.9471(6) 0.3970(4) 0.0448(11) Uani 1 1 d . . . H4A H 0.1230 1.0044 0.4256 0.054 Uiso 1 1 calc R . . C5 C 0.3075(7) 0.9890(6) 0.2951(4) 0.0465(11) Uani 1 1 d . . . H5A H 0.2721 1.0711 0.2580 0.056 Uiso 1 1 calc R . . C6 C 0.4440(7) 0.9139(6) 0.2512(4) 0.0405(10) Uani 1 1 d . . . H6A H 0.5040 0.9445 0.1852 0.049 Uiso 1 1 calc R . . C1 C 0.4964(6) 0.7856(5) 0.3073(4) 0.0349(9) Uani 1 1 d . . . C7 C 0.7347(9) 0.7273(8) 0.1700(5) 0.0597(14) Uani 1 1 d . . . H7A H 0.6983 0.8161 0.1364 0.090 Uiso 1 1 calc R . . H7B H 0.6926 0.6195 0.1095 0.090 Uiso 1 1 calc R . . H7C H 0.8821 0.7629 0.1954 0.090 Uiso 1 1 calc R . . S1' S 1.01316(18) 0.32338(15) 0.21138(11) 0.0426(3) Uani 1 1 d . . . O1' O 0.9871(5) 0.4929(4) 0.2497(3) 0.0587(9) Uani 1 1 d . . . O2' O 0.9386(6) 0.2045(5) 0.2865(3) 0.0685(11) Uani 1 1 d . . . O3' O 1.2089(6) 0.3276(5) 0.1761(4) 0.0706(11) Uani 1 1 d . . . C1' C 0.8317(8) 0.2317(6) 0.0705(5) 0.0485(12) Uani 1 1 d . . . F1' F 0.8788(6) 0.3237(5) -0.0115(3) 0.0861(11) Uani 1 1 d . . . F2' F 0.6409(5) 0.2291(5) 0.0884(3) 0.0815(10) Uani 1 1 d . . . F3' F 0.8196(7) 0.0706(4) 0.0235(3) 0.0928(12) 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 Te 0.03740(17) 0.03726(16) 0.04104(18) 0.01358(12) 0.00597(12) 0.01524(12) N2 0.0329(18) 0.0341(18) 0.038(2) 0.0131(15) 0.0048(16) 0.0094(15) N1 0.0367(19) 0.0410(19) 0.036(2) 0.0158(16) 0.0056(16) 0.0119(16) C2 0.030(2) 0.031(2) 0.031(2) 0.0057(16) -0.0017(17) 0.0075(16) C3 0.037(2) 0.038(2) 0.039(2) 0.0042(19) 0.0041(19) 0.0103(19) C4 0.042(3) 0.043(2) 0.051(3) 0.008(2) 0.003(2) 0.019(2) C5 0.053(3) 0.039(2) 0.051(3) 0.013(2) 0.002(2) 0.019(2) C6 0.043(2) 0.043(2) 0.039(3) 0.015(2) 0.003(2) 0.016(2) C1 0.035(2) 0.031(2) 0.036(2) 0.0083(17) 0.0005(18) 0.0060(17) C7 0.071(4) 0.069(3) 0.066(4) 0.035(3) 0.035(3) 0.042(3) S1' 0.0401(6) 0.0472(6) 0.0431(7) 0.0088(5) 0.0048(5) 0.0189(5) O1' 0.056(2) 0.0480(19) 0.068(2) -0.0008(17) 0.0072(19) 0.0197(17) O2' 0.080(3) 0.082(3) 0.053(2) 0.033(2) 0.009(2) 0.029(2) O3' 0.045(2) 0.087(3) 0.088(3) 0.017(2) 0.014(2) 0.033(2) C1' 0.055(3) 0.042(3) 0.046(3) 0.010(2) 0.005(2) 0.013(2) F1' 0.107(3) 0.088(2) 0.0505(19) 0.0350(18) 0.0040(19) 0.000(2) F2' 0.0479(18) 0.104(3) 0.083(2) 0.020(2) -0.0075(17) 0.0153(18) F3' 0.138(3) 0.0487(19) 0.074(2) -0.0075(17) -0.004(2) 0.022(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Te N2 1.990(4) . ? Te N1 2.093(3) . ? Te N2 2.417(3) 2_666 ? N2 C2 1.319(5) . ? N2 Te 2.417(3) 2_666 ? N1 C1 1.317(6) . ? N1 C7 1.473(6) . ? C2 C3 1.424(6) . ? C2 C1 1.452(6) . ? C3 C4 1.347(6) . ? C4 C5 1.424(7) . ? C5 C6 1.337(7) . ? C6 C1 1.434(6) . ? S1' O3' 1.422(4) . ? S1' O2' 1.432(4) . ? S1' O1' 1.439(3) . ? S1' C1' 1.813(5) . ? C1' F3' 1.301(6) . ? C1' F1' 1.313(6) . ? C1' F2' 1.329(6) . ? 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 Te N1 79.38(14) . . ? N2 Te N2 70.68(14) . 2_666 ? N1 Te N2 150.00(14) . 2_666 ? C2 N2 Te 115.5(3) . . ? C2 N2 Te 135.2(3) . 2_666 ? Te N2 Te 109.32(14) . 2_666 ? C1 N1 C7 121.8(4) . . ? C1 N1 Te 113.1(3) . . ? C7 N1 Te 125.0(3) . . ? N2 C2 C3 123.7(4) . . ? N2 C2 C1 117.0(4) . . ? C3 C2 C1 119.2(4) . . ? C4 C3 C2 118.9(4) . . ? C3 C4 C5 121.9(4) . . ? C6 C5 C4 122.0(4) . . ? C5 C6 C1 119.0(4) . . ? N1 C1 C6 126.0(4) . . ? N1 C1 C2 115.0(4) . . ? C6 C1 C2 119.0(4) . . ? O3' S1' O2' 116.0(3) . . ? O3' S1' O1' 114.4(2) . . ? O2' S1' O1' 114.1(2) . . ? O3' S1' C1' 104.0(2) . . ? O2' S1' C1' 103.5(2) . . ? O1' S1' C1' 102.5(2) . . ? F3' C1' F1' 108.1(5) . . ? F3' C1' F2' 106.0(4) . . ? F1' C1' F2' 106.7(4) . . ? F3' C1' S1' 112.8(4) . . ? F1' C1' S1' 112.1(3) . . ? F2' C1' S1' 110.8(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.34 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.608 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.094