# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Ashok Chauhan' 'Raymond J. Butcher' 'Andrew Duthie' 'Shafalika Misra' 'Puspendra Singh' 'Ramesh C. Srivastava' _publ_contact_author_name 'Ashok Chauhan' _publ_contact_author_email AKSCHAUHAN2003@YAHOO.CO.IN _publ_section_title ; Amidomethylation of elemental tellurium: Synthesis and solid state structures of N-substituted amidomethyltellurium(IV&II) derivatives ; # Attachment 'CIF - 1b.cif' data_AKSC082 _database_code_depnum_ccdc_archive 'CCDC 751763' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H24 Br2 N2 O2 Te' _chemical_formula_sum 'C12 H24 Br2 N2 O2 Te' _chemical_formula_weight 515.75 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' Br Br -0.2901 2.4595 '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' Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnaa _symmetry_space_group_name_Hall '-P 2ac 2bc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x, y-1/2, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 10.0602(3) _cell_length_b 11.9199(5) _cell_length_c 15.2972(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1834.39(11) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 3040 _cell_measurement_theta_min 4.5839 _cell_measurement_theta_max 32.4515 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.27 _exptl_crystal_density_diffrn 1.867 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 5.978 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1696 _exptl_absorpt_correction_T_max 0.2952 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Oxford Diffraction Gemini' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 7256 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1596 _reflns_number_gt 1069 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0352P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0034(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1596 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0248 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0564 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 C1 C 0.1920(3) 0.2095(4) 0.1502(3) 0.0232(10) Uani 1 1 d . . . H1A H 0.2487 0.2749 0.1360 0.028 Uiso 1 1 calc R . . H1B H 0.2493 0.1460 0.1681 0.028 Uiso 1 1 calc R . . C2 C 0.1046(4) 0.1778(4) 0.0737(3) 0.0215(9) Uani 1 1 d . . . C3 C 0.2978(4) 0.0853(4) 0.0041(3) 0.0322(12) Uani 1 1 d . . . H3A H 0.3522 0.1316 0.0442 0.039 Uiso 1 1 calc R . . H3B H 0.3343 0.0939 -0.0556 0.039 Uiso 1 1 calc R . . C4 C 0.3071(4) -0.0356(4) 0.0311(3) 0.0402(13) Uani 1 1 d . . . H4A H 0.3999 -0.0601 0.0284 0.060 Uiso 1 1 calc R . . H4B H 0.2532 -0.0817 -0.0084 0.060 Uiso 1 1 calc R . . H4C H 0.2740 -0.0439 0.0910 0.060 Uiso 1 1 calc R . . C5 C 0.0770(4) 0.1011(4) -0.0722(3) 0.0311(11) Uani 1 1 d . . . H5A H -0.0165 0.0904 -0.0537 0.037 Uiso 1 1 calc R . . H5B H 0.1079 0.0304 -0.0993 0.037 Uiso 1 1 calc R . . C6 C 0.0837(6) 0.1940(5) -0.1388(3) 0.0693(18) Uani 1 1 d . . . H6A H 0.0271 0.1752 -0.1888 0.104 Uiso 1 1 calc R . . H6B H 0.1757 0.2033 -0.1585 0.104 Uiso 1 1 calc R . . H6C H 0.0526 0.2641 -0.1123 0.104 Uiso 1 1 calc R . . Br Br 0.06151(5) 0.46547(4) 0.20669(3) 0.0507(2) Uani 1 1 d . . . N N 0.1596(3) 0.1258(3) 0.0055(2) 0.0263(9) Uani 1 1 d . . . O O -0.0150(3) 0.2022(3) 0.07710(18) 0.0289(7) Uani 1 1 d . . . Te Te 0.05154(3) 0.2500 0.2500 0.02197(15) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.021(2) 0.030(3) 0.019(2) -0.0035(19) 0.0004(16) 0.0009(18) C2 0.025(2) 0.019(2) 0.021(2) 0.004(2) 0.0012(18) -0.003(2) C3 0.025(2) 0.038(3) 0.033(3) -0.012(2) 0.0075(18) -0.003(2) C4 0.028(2) 0.036(3) 0.057(4) -0.013(3) 0.003(2) 0.006(2) C5 0.041(3) 0.030(3) 0.023(2) -0.008(2) -0.0062(19) -0.002(2) C6 0.125(5) 0.048(4) 0.034(3) 0.008(3) -0.024(3) -0.028(4) Br 0.0850(4) 0.0320(3) 0.0350(3) 0.0044(2) 0.0036(3) 0.0133(3) N 0.0249(17) 0.032(2) 0.0222(19) -0.0080(18) 0.0026(15) -0.0032(17) O 0.0261(15) 0.0336(19) 0.0268(16) -0.0055(14) -0.0047(12) 0.0076(14) Te 0.0201(2) 0.0297(3) 0.0160(2) -0.00172(19) 0.000 0.000 _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 C2 1.512(5) . ? C1 Te 2.135(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O 1.239(4) . ? C2 N 1.333(5) . ? C3 N 1.472(5) . ? C3 C4 1.502(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N 1.480(5) . ? C5 C6 1.506(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? O Te 2.787(3) . ? Br Te 2.6543(5) . ? Te C1 2.135(4) 3 ? Te Br 2.6543(5) 3 ? 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 C2 C1 Te 103.0(2) . . ? C2 C1 H1A 111.2 . . ? Te C1 H1A 111.2 . . ? C2 C1 H1B 111.2 . . ? Te C1 H1B 111.2 . . ? H1A C1 H1B 109.1 . . ? O C2 N 123.0(4) . . ? O C2 C1 118.3(3) . . ? N C2 C1 118.7(3) . . ? N C3 C4 111.7(3) . . ? N C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? N C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N C5 C6 111.9(4) . . ? N C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? N C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 N C3 123.8(3) . . ? C2 N C5 119.2(3) . . ? C3 N C5 116.9(3) . . ? C1 Te C1 97.12(19) 3 . ? C1 Te Br 86.25(12) 3 . ? C1 Te Br 90.88(12) . . ? C1 Te Br 90.88(12) 3 3 ? C1 Te Br 86.25(12) . 3 ? Br Te Br 175.67(3) . 3 ? C1 Te O 152.06(11) 3 . ? C1 Te O 55.56(11) . . ? Br Te O 88.28(6) . . ? Br Te O 92.76(6) 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 Te C1 C2 O 14.1(5) . . . . ? Te C1 C2 N -166.4(3) . . . . ? O C2 N C3 -173.2(4) . . . . ? C1 C2 N C3 7.4(6) . . . . ? O C2 N C5 3.5(6) . . . . ? C1 C2 N C5 -175.9(4) . . . . ? C4 C3 N C2 93.8(5) . . . . ? C4 C3 N C5 -82.9(5) . . . . ? C6 C5 N C2 91.7(5) . . . . ? C6 C5 N C3 -91.4(5) . . . . ? C2 C1 Te C1 179.7(4) . . . 3 ? C2 C1 Te Br -94.0(3) . . . . ? C2 C1 Te Br 89.3(3) . . . 3 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.160 _refine_diff_density_min -0.793 _refine_diff_density_rms 0.103 # Attachment 'CIF- 2b.cif' data_AKSC_AM6 _database_code_depnum_ccdc_archive 'CCDC 751764' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 Br2 N2 O2 Te' _chemical_formula_sum 'C18 H20 Br2 N2 O2 Te' _chemical_formula_weight 583.78 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' Br Br -0.2901 2.4595 '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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.3878(4) _cell_length_b 21.5374(9) _cell_length_c 10.6418(5) _cell_angle_alpha 90.00 _cell_angle_beta 112.687(5) _cell_angle_gamma 90.00 _cell_volume 2196.63(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4214 _cell_measurement_theta_min 4.6468 _cell_measurement_theta_max 32.5545 _exptl_crystal_description Needle _exptl_crystal_colour Orange _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.765 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 5.005 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1846 _exptl_absorpt_correction_T_max 0.4661 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'Oxford Diffraction Gemini' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 13184 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3842 _reflns_number_gt 2231 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0447P)^2^+3.9676P] 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 0.0104(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3842 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 C1 C 0.0683(7) 0.2284(4) 0.3387(8) 0.069(2) Uani 1 1 d . . . H1A H 0.0027 0.1941 0.3128 0.083 Uiso 1 1 calc R . . H1B H 0.0669 0.2473 0.4209 0.083 Uiso 1 1 calc R . . C2 C 0.0328(7) 0.2749(3) 0.2265(6) 0.0562(17) Uani 1 1 d . A . C3 C -0.1192(9) 0.3564(5) 0.0919(9) 0.103(3) Uani 1 1 d . A . H3A H -0.0511 0.3891 0.1131 0.154 Uiso 1 1 calc R . . H3B H -0.2086 0.3738 0.0789 0.154 Uiso 1 1 calc R . . H3C H -0.1247 0.3358 0.0101 0.154 Uiso 1 1 calc R . . C4 C -0.1521(13) 0.3145(7) 0.2961(10) 0.0538(19) Uani 0.610(15) 1 d PG A 1 C5 C -0.2819(14) 0.2859(7) 0.2547(12) 0.066(4) Uani 0.610(15) 1 d PG A 1 H5 H -0.3172 0.2644 0.1725 0.079 Uiso 0.610(15) 1 calc PR A 1 C6 C -0.3589(12) 0.2892(9) 0.3362(17) 0.090(5) Uani 0.610(15) 1 d PG A 1 H6 H -0.4457 0.2701 0.3085 0.108 Uiso 0.610(15) 1 calc PR A 1 C7 C -0.3061(14) 0.3213(8) 0.4590(14) 0.093(3) Uani 0.610(15) 1 d PG A 1 H7 H -0.3576 0.3235 0.5136 0.111 Uiso 0.610(15) 1 calc PR A 1 C8 C -0.1764(16) 0.3499(7) 0.5004(12) 0.078(4) Uani 0.610(15) 1 d PG A 1 H8 H -0.1411 0.3713 0.5826 0.094 Uiso 0.610(15) 1 calc PR A 1 C9 C -0.0994(13) 0.3465(7) 0.4189(13) 0.067(4) Uani 0.610(15) 1 d PG A 1 H9 H -0.0126 0.3656 0.4466 0.081 Uiso 0.610(15) 1 calc PR A 1 C4' C -0.154(2) 0.3093(11) 0.2862(17) 0.0538(19) Uani 0.390(15) 1 d PG A 2 C5' C -0.246(2) 0.2626(10) 0.288(2) 0.066(4) Uani 0.390(15) 1 d PG A 2 H5' H -0.2568 0.2276 0.2340 0.079 Uiso 0.390(15) 1 calc PR A 2 C6' C -0.320(2) 0.2683(11) 0.371(3) 0.090(5) Uani 0.390(15) 1 d PG A 2 H6' H -0.3816 0.2370 0.3728 0.108 Uiso 0.390(15) 1 calc PR A 2 C7' C -0.304(2) 0.3207(13) 0.453(2) 0.093(3) Uani 0.390(15) 1 d PG A 2 H7' H -0.3538 0.3244 0.5082 0.111 Uiso 0.390(15) 1 calc PR A 2 C8' C -0.212(3) 0.3674(11) 0.450(2) 0.078(4) Uani 0.390(15) 1 d PG A 2 H8' H -0.2011 0.4024 0.5047 0.094 Uiso 0.390(15) 1 calc PR A 2 C9' C -0.137(2) 0.3617(10) 0.367(2) 0.067(4) Uani 0.390(15) 1 d PG A 2 H9' H -0.0763 0.3930 0.3658 0.081 Uiso 0.390(15) 1 calc PR A 2 N1 N -0.0778(6) 0.3113(3) 0.2055(5) 0.0624(16) Uani 1 1 d . . . O1 O 0.1037(5) 0.2781(3) 0.1573(5) 0.0755(15) Uani 1 1 d . . . C11 C 0.2971(8) 0.1432(4) 0.5454(8) 0.073(2) Uani 1 1 d . . . H11A H 0.3073 0.1698 0.6222 0.087 Uiso 1 1 calc R A . H11B H 0.2172 0.1163 0.5276 0.087 Uiso 1 1 calc R . . C12 C 0.4269(8) 0.1059(3) 0.5726(7) 0.0587(18) Uani 1 1 d . A . C13 C 0.5765(10) 0.0204(4) 0.6932(9) 0.102(3) Uani 1 1 d . A . H13A H 0.6218 0.0300 0.6321 0.154 Uiso 1 1 calc R . . H13B H 0.5542 -0.0230 0.6872 0.154 Uiso 1 1 calc R . . H13C H 0.6377 0.0304 0.7847 0.154 Uiso 1 1 calc R . . C14 C 0.3410(15) 0.0405(8) 0.7068(15) 0.062(3) Uani 0.68(2) 1 d PG A 1 C15 C 0.231(2) 0.0006(8) 0.6384(12) 0.088(5) Uani 0.68(2) 1 d PG A 1 H15 H 0.2219 -0.0161 0.5548 0.106 Uiso 0.68(2) 1 calc PR A 1 C16 C 0.1348(17) -0.0144(8) 0.6951(14) 0.118(7) Uani 0.68(2) 1 d PG A 1 H16 H 0.0613 -0.0411 0.6493 0.142 Uiso 0.68(2) 1 calc PR A 1 C17 C 0.1486(15) 0.0105(8) 0.8201(16) 0.110(5) Uani 0.68(2) 1 d PG A 1 H17 H 0.0842 0.0005 0.8580 0.132 Uiso 0.68(2) 1 calc PR A 1 C18 C 0.2585(18) 0.0504(8) 0.8885(14) 0.111(4) Uani 0.32(2) 1 d PG A 1 H18 H 0.2677 0.0671 0.9721 0.134 Uiso 0.32(2) 1 calc PR A 1 C19 C 0.3548(15) 0.0654(9) 0.8318(16) 0.095(3) Uani 0.68(2) 1 d PG A 1 H19 H 0.4283 0.0921 0.8775 0.114 Uiso 0.68(2) 1 calc PR A 1 C14' C 0.370(3) 0.0360(18) 0.725(3) 0.062(3) Uani 0.32(2) 1 d PG A 2 C15' C 0.298(4) -0.0188(15) 0.675(3) 0.088(5) Uani 0.32(2) 1 d PG A 2 H15' H 0.3148 -0.0412 0.6084 0.106 Uiso 0.32(2) 1 calc PR A 2 C16' C 0.200(4) -0.0402(11) 0.724(4) 0.118(7) Uani 0.32(2) 1 d PG A 2 H16' H 0.1515 -0.0769 0.6906 0.142 Uiso 0.32(2) 1 calc PR A 2 C17' C 0.174(4) -0.0068(10) 0.824(3) 0.110(5) Uani 0.32(2) 1 d PG A 2 H17' H 0.1085 -0.0211 0.8569 0.132 Uiso 0.32(2) 1 calc PR A 2 C18' C 0.246(2) 0.0480(9) 0.8743(17) 0.111(4) Uani 0.68(2) 1 d PG A 2 H18' H 0.2289 0.0703 0.9410 0.134 Uiso 0.68(2) 1 calc PR A 2 C19' C 0.344(3) 0.0694(14) 0.825(3) 0.095(3) Uani 0.32(2) 1 d PG A 2 H19' H 0.3922 0.1061 0.8587 0.114 Uiso 0.32(2) 1 calc PR A 2 N2 N 0.4476(6) 0.0570(3) 0.6556(6) 0.0663(16) Uani 1 1 d . . . O2 O 0.5106(5) 0.1212(2) 0.5222(5) 0.0752(14) Uani 1 1 d . . . Br1 Br 0.36793(10) 0.29415(4) 0.53343(10) 0.0922(3) Uani 1 1 d . . . Br2 Br 0.16475(10) 0.09476(5) 0.22693(12) 0.1075(4) Uani 1 1 d . . . Te Te 0.27418(5) 0.19701(2) 0.36990(5) 0.0646(2) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.053(4) 0.082(5) 0.091(5) 0.030(4) 0.048(4) 0.025(4) C2 0.060(4) 0.068(5) 0.050(4) 0.011(3) 0.032(3) 0.010(4) C3 0.090(6) 0.136(9) 0.095(6) 0.063(6) 0.049(5) 0.048(6) C4 0.048(4) 0.069(5) 0.048(4) 0.006(4) 0.022(3) 0.018(4) C5 0.047(9) 0.092(13) 0.054(8) 0.013(7) 0.013(6) 0.009(8) C6 0.033(8) 0.160(17) 0.073(11) 0.021(9) 0.016(8) 0.002(9) C7 0.062(5) 0.152(10) 0.081(7) 0.026(6) 0.046(5) 0.028(5) C8 0.117(12) 0.081(11) 0.046(10) 0.016(8) 0.042(9) 0.030(8) C9 0.074(9) 0.084(10) 0.044(10) 0.015(7) 0.023(8) 0.007(7) C4' 0.048(4) 0.069(5) 0.048(4) 0.006(4) 0.022(3) 0.018(4) C5' 0.047(9) 0.092(13) 0.054(8) 0.013(7) 0.013(6) 0.009(8) C6' 0.033(8) 0.160(17) 0.073(11) 0.021(9) 0.016(8) 0.002(9) C7' 0.062(5) 0.152(10) 0.081(7) 0.026(6) 0.046(5) 0.028(5) C8' 0.117(12) 0.081(11) 0.046(10) 0.016(8) 0.042(9) 0.030(8) C9' 0.074(9) 0.084(10) 0.044(10) 0.015(7) 0.023(8) 0.007(7) N1 0.058(3) 0.081(4) 0.059(3) 0.022(3) 0.035(3) 0.021(3) O1 0.078(3) 0.102(4) 0.071(3) 0.022(3) 0.056(3) 0.019(3) C11 0.088(5) 0.069(5) 0.087(5) 0.032(4) 0.061(5) 0.025(4) C12 0.076(5) 0.047(4) 0.070(5) 0.001(4) 0.047(4) 0.011(4) C13 0.116(7) 0.099(7) 0.091(6) 0.022(5) 0.038(5) 0.060(6) C14 0.079(8) 0.045(5) 0.055(6) 0.004(5) 0.017(6) 0.006(6) C15 0.117(16) 0.069(11) 0.079(9) -0.006(7) 0.039(10) -0.020(10) C16 0.161(19) 0.078(13) 0.135(13) -0.010(11) 0.079(13) -0.042(13) C17 0.162(13) 0.058(10) 0.141(10) 0.022(9) 0.093(10) -0.013(9) C18 0.159(11) 0.083(7) 0.119(9) -0.022(6) 0.084(8) -0.020(7) C19 0.103(7) 0.092(7) 0.107(7) -0.022(6) 0.058(6) -0.024(6) C14' 0.079(8) 0.045(5) 0.055(6) 0.004(5) 0.017(6) 0.006(6) C15' 0.117(16) 0.069(11) 0.079(9) -0.006(7) 0.039(10) -0.020(10) C16' 0.161(19) 0.078(13) 0.135(13) -0.010(11) 0.079(13) -0.042(13) C17' 0.162(13) 0.058(10) 0.141(10) 0.022(9) 0.093(10) -0.013(9) C18' 0.159(11) 0.083(7) 0.119(9) -0.022(6) 0.084(8) -0.020(7) C19' 0.103(7) 0.092(7) 0.107(7) -0.022(6) 0.058(6) -0.024(6) N2 0.071(4) 0.057(4) 0.073(4) 0.006(3) 0.029(3) 0.016(3) O2 0.063(3) 0.088(4) 0.089(4) 0.010(3) 0.045(3) 0.018(3) Br1 0.0911(6) 0.0869(7) 0.1184(8) 0.0123(5) 0.0623(6) 0.0022(5) Br2 0.0894(7) 0.0990(8) 0.1429(9) -0.0044(6) 0.0546(6) 0.0133(6) Te 0.0575(3) 0.0730(4) 0.0845(4) 0.0261(3) 0.0507(3) 0.0207(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 C1 C2 1.493(9) . ? C1 Te 2.143(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 O1 1.228(7) . ? C2 N1 1.336(8) . ? C3 N1 1.479(9) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.3900 . ? C4 C9 1.3900 . ? C4 N1 1.451(12) . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 C7 1.3900 . ? C6 H6 0.9300 . ? C7 C8 1.3900 . ? C7 H7 0.9300 . ? C8 C9 1.3900 . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C4' N1 1.376(19) . ? C4' C5' 1.3900 . ? C4' C9' 1.3900 . ? C5' C6' 1.3900 . ? C5' H5' 0.9300 . ? C6' C7' 1.3900 . ? C6' H6' 0.9300 . ? C7' C8' 1.3900 . ? C7' H7' 0.9300 . ? C8' C9' 1.3900 . ? C8' H8' 0.9300 . ? C9' H9' 0.9300 . ? O1 Te 2.866(5) . ? C11 C12 1.499(9) . ? C11 Te 2.131(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O2 1.229(8) . ? C12 N2 1.338(8) . ? C13 N2 1.470(9) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.3900 . ? C14 C19 1.3900 . ? C14 N2 1.454(12) . ? C15 C16 1.3900 . ? C15 H15 0.9300 . ? C16 C17 1.3900 . ? C16 H16 0.9300 . ? C17 C18 1.3900 . ? C17 H17 0.9300 . ? C18 C19 1.3900 . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C14' N2 1.37(2) . ? C14' C15' 1.3900 . ? C14' C19' 1.3900 . ? C15' C16' 1.3900 . ? C15' H15' 0.9300 . ? C16' C17' 1.3900 . ? C16' H16' 0.9300 . ? C17' C18' 1.3900 . ? C17' H17' 0.9300 . ? C18' C19' 1.3900 . ? C18' H18' 0.9300 . ? C19' H19' 0.9300 . ? O2 Te 2.873(5) . ? Br1 Te 2.6546(12) . ? Br2 Te 2.6688(13) . ? 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 C2 C1 Te 105.0(4) . . ? C2 C1 H1A 110.7 . . ? Te C1 H1A 110.7 . . ? C2 C1 H1B 110.7 . . ? Te C1 H1B 110.7 . . ? H1A C1 H1B 108.8 . . ? O1 C2 N1 122.9(6) . . ? O1 C2 C1 119.8(6) . . ? N1 C2 C1 117.3(6) . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C9 120.0 . . ? C5 C4 N1 117.9(10) . . ? C9 C4 N1 122.0(10) . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.0 . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.0 . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 120.0 . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C4 120.0 . . ? C8 C9 H9 120.0 . . ? C4 C9 H9 120.0 . . ? N1 C4' C5' 126.5(18) . . ? N1 C4' C9' 113.5(18) . . ? C5' C4' C9' 120.0 . . ? C4' C5' C6' 120.0 . . ? C4' C5' H5' 120.0 . . ? C6' C5' H5' 120.0 . . ? C7' C6' C5' 120.0 . . ? C7' C6' H6' 120.0 . . ? C5' C6' H6' 120.0 . . ? C6' C7' C8' 120.0 . . ? C6' C7' H7' 120.0 . . ? C8' C7' H7' 120.0 . . ? C9' C8' C7' 120.0 . . ? C9' C8' H8' 120.0 . . ? C7' C8' H8' 120.0 . . ? C8' C9' C4' 120.0 . . ? C8' C9' H9' 120.0 . . ? C4' C9' H9' 120.0 . . ? C2 N1 C4' 122.9(8) . . ? C2 N1 C4 124.1(6) . . ? C2 N1 C3 118.8(6) . . ? C4' N1 C3 118.3(9) . . ? C4 N1 C3 116.8(7) . . ? C2 O1 Te 79.8(4) . . ? C12 C11 Te 104.4(4) . . ? C12 C11 H11A 110.9 . . ? Te C11 H11A 110.9 . . ? C12 C11 H11B 110.9 . . ? Te C11 H11B 110.9 . . ? H11A C11 H11B 108.9 . . ? O2 C12 N2 122.6(6) . . ? O2 C12 C11 120.5(6) . . ? N2 C12 C11 116.9(6) . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 120.0 . . ? C15 C14 N2 123.1(10) . . ? C19 C14 N2 116.9(10) . . ? C16 C15 C14 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.0 . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 120.0 . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.0 . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 C14 120.0 . . ? C18 C19 H19 120.0 . . ? C14 C19 H19 120.0 . . ? N2 C14' C15' 115(2) . . ? N2 C14' C19' 125(2) . . ? C15' C14' C19' 120.0 . . ? C16' C15' C14' 120.0 . . ? C16' C15' H15' 120.0 . . ? C14' C15' H15' 120.0 . . ? C15' C16' C17' 120.0 . . ? C15' C16' H16' 120.0 . . ? C17' C16' H16' 120.0 . . ? C18' C17' C16' 120.0 . . ? C18' C17' H17' 120.0 . . ? C16' C17' H17' 120.0 . . ? C19' C18' C17' 120.0 . . ? C19' C18' H18' 120.0 . . ? C17' C18' H18' 120.0 . . ? C18' C19' C14' 120.0 . . ? C18' C19' H19' 120.0 . . ? C14' C19' H19' 120.0 . . ? C12 N2 C14' 129.9(18) . . ? C12 N2 C14 119.3(9) . . ? C12 N2 C13 119.9(7) . . ? C14' N2 C13 110.0(18) . . ? C14 N2 C13 120.8(9) . . ? C12 O2 Te 78.7(4) . . ? C11 Te C1 94.3(3) . . ? C11 Te Br1 88.0(2) . . ? C1 Te Br1 86.8(2) . . ? C11 Te Br2 86.0(2) . . ? C1 Te Br2 89.5(2) . . ? Br1 Te Br2 172.73(3) . . ? C11 Te O1 148.1(2) . . ? C1 Te O1 53.8(2) . . ? Br1 Te O1 89.76(12) . . ? Br2 Te O1 93.18(12) . . ? C11 Te O2 54.2(2) . . ? C1 Te O2 148.4(2) . . ? Br1 Te O2 93.45(11) . . ? Br2 Te O2 86.35(11) . . ? O1 Te O2 157.69(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Te C1 C2 O1 14.3(9) . . . . ? Te C1 C2 N1 -166.4(5) . . . . ? C9 C4 C5 C6 0.0 . . . . ? N1 C4 C5 C6 -178.0(10) . . . . ? C4 C5 C6 C7 0.0 . . . . ? C5 C6 C7 C8 0.0 . . . . ? C6 C7 C8 C9 0.0 . . . . ? C7 C8 C9 C4 0.0 . . . . ? C5 C4 C9 C8 0.0 . . . . ? N1 C4 C9 C8 178.0(10) . . . . ? N1 C4' C5' C6' -177.2(15) . . . . ? C9' C4' C5' C6' 0.0 . . . . ? C4' C5' C6' C7' 0.0 . . . . ? C5' C6' C7' C8' 0.0 . . . . ? C6' C7' C8' C9' 0.0 . . . . ? C7' C8' C9' C4' 0.0 . . . . ? N1 C4' C9' C8' 177.6(13) . . . . ? C5' C4' C9' C8' 0.0 . . . . ? O1 C2 N1 C4' -177.5(14) . . . . ? C1 C2 N1 C4' 3.1(16) . . . . ? O1 C2 N1 C4 -171.4(10) . . . . ? C1 C2 N1 C4 9.2(13) . . . . ? O1 C2 N1 C3 1.6(12) . . . . ? C1 C2 N1 C3 -177.8(7) . . . . ? C5' C4' N1 C2 -72.7(15) . . . . ? C9' C4' N1 C2 109.9(12) . . . . ? C5' C4' N1 C4 -177(11) . . . . ? C9' C4' N1 C4 5(10) . . . . ? C5' C4' N1 C3 108.3(14) . . . . ? C9' C4' N1 C3 -69.1(13) . . . . ? C5 C4 N1 C2 -105.6(10) . . . . ? C9 C4 N1 C2 76.4(12) . . . . ? C5 C4 N1 C4' -27(10) . . . . ? C9 C4 N1 C4' 155(11) . . . . ? C5 C4 N1 C3 81.3(11) . . . . ? C9 C4 N1 C3 -96.7(9) . . . . ? N1 C2 O1 Te 170.3(7) . . . . ? C1 C2 O1 Te -10.4(6) . . . . ? Te C11 C12 O2 17.8(9) . . . . ? Te C11 C12 N2 -163.8(5) . . . . ? C19 C14 C15 C16 0.0 . . . . ? N2 C14 C15 C16 178.4(13) . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C14 0.0 . . . . ? C15 C14 C19 C18 0.0 . . . . ? N2 C14 C19 C18 -178.5(13) . . . . ? N2 C14' C15' C16' -171(3) . . . . ? C19' C14' C15' C16' 0.0 . . . . ? C14' C15' C16' C17' 0.0 . . . . ? C15' C16' C17' C18' 0.0 . . . . ? C16' C17' C18' C19' 0.0 . . . . ? C17' C18' C19' C14' 0.0 . . . . ? N2 C14' C19' C18' 170(4) . . . . ? C15' C14' C19' C18' 0.0 . . . . ? O2 C12 N2 C14' 176.0(19) . . . . ? C11 C12 N2 C14' -2(2) . . . . ? O2 C12 N2 C14 -177.6(9) . . . . ? C11 C12 N2 C14 4.0(11) . . . . ? O2 C12 N2 C13 1.9(11) . . . . ? C11 C12 N2 C13 -176.5(7) . . . . ? C15' C14' N2 C12 109(2) . . . . ? C19' C14' N2 C12 -62(3) . . . . ? C15' C14' N2 C14 80(9) . . . . ? C19' C14' N2 C14 -90(9) . . . . ? C15' C14' N2 C13 -77(2) . . . . ? C19' C14' N2 C13 112.7(17) . . . . ? C15 C14 N2 C12 88.7(13) . . . . ? C19 C14 N2 C12 -92.8(11) . . . . ? C15 C14 N2 C14' -116(10) . . . . ? C19 C14 N2 C14' 62(9) . . . . ? C15 C14 N2 C13 -90.8(13) . . . . ? C19 C14 N2 C13 87.7(11) . . . . ? N2 C12 O2 Te 168.7(7) . . . . ? C11 C12 O2 Te -12.9(6) . . . . ? C12 C11 Te C1 169.6(5) . . . . ? C12 C11 Te Br1 -103.7(5) . . . . ? C12 C11 Te Br2 80.4(5) . . . . ? C12 C11 Te O1 170.0(4) . . . . ? C12 C11 Te O2 -8.0(4) . . . . ? C2 C1 Te C11 173.2(5) . . . . ? C2 C1 Te Br1 85.5(5) . . . . ? C2 C1 Te Br2 -100.8(5) . . . . ? C2 C1 Te O1 -6.5(4) . . . . ? C2 C1 Te O2 177.0(4) . . . . ? C2 O1 Te C11 7.3(7) . . . . ? C2 O1 Te C1 7.8(5) . . . . ? C2 O1 Te Br1 -78.5(4) . . . . ? C2 O1 Te Br2 94.9(4) . . . . ? C2 O1 Te O2 -177.0(4) . . . . ? C12 O2 Te C11 9.6(5) . . . . ? C12 O2 Te C1 5.1(7) . . . . ? C12 O2 Te Br1 94.7(4) . . . . ? C12 O2 Te Br2 -78.1(4) . . . . ? C12 O2 Te O1 -167.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.102 _refine_diff_density_min -0.708 _refine_diff_density_rms 0.101 # Attachment 'CIF-1c.cif' data_AKSC083 _database_code_depnum_ccdc_archive 'CCDC 751765' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H24 I2 N2 O2 Te' _chemical_formula_sum 'C12 H24 I2 N2 O2 Te' _chemical_formula_weight 609.73 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' I I -0.4742 1.8119 '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' Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnaa _symmetry_space_group_name_Hall '-P 2ac 2bc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x, y-1/2, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 10.1737(4) _cell_length_b 12.0732(4) _cell_length_c 15.7948(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1940.06(11) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 5101 _cell_measurement_theta_min 4.6673 _cell_measurement_theta_max 32.3747 _exptl_crystal_description Prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.32 _exptl_crystal_density_diffrn 2.088 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 4.717 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1971 _exptl_absorpt_correction_T_max 0.3137 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Oxford Diffraction Gemini' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 7661 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.67 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1697 _reflns_number_gt 1347 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0365P)^2^+3.9638P] 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 0.0068(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1697 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0742 _refine_ls_wR_factor_gt 0.0689 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 C1 C 0.1923(4) 0.2129(4) 0.1519(3) 0.0272(10) Uani 1 1 d . . . H1A H 0.2477 0.2780 0.1386 0.033 Uiso 1 1 calc R . . H1B H 0.2495 0.1500 0.1679 0.033 Uiso 1 1 calc R . . C2 C 0.1041(5) 0.1830(4) 0.0780(3) 0.0245(10) Uani 1 1 d . . . C3 C 0.0727(5) 0.1129(4) -0.0642(3) 0.0338(12) Uani 1 1 d . . . H3A H -0.0190 0.1009 -0.0455 0.041 Uiso 1 1 calc R . . H3B H 0.1029 0.0447 -0.0930 0.041 Uiso 1 1 calc R . . C4 C 0.0766(7) 0.2076(5) -0.1256(4) 0.068(2) Uani 1 1 d . . . H4A H 0.0197 0.1910 -0.1740 0.102 Uiso 1 1 calc R . . H4B H 0.1670 0.2185 -0.1454 0.102 Uiso 1 1 calc R . . H4C H 0.0457 0.2751 -0.0975 0.102 Uiso 1 1 calc R . . C5 C 0.2929(5) 0.0940(4) 0.0059(3) 0.0339(11) Uani 1 1 d . . . H5A H 0.3474 0.1362 0.0465 0.041 Uiso 1 1 calc R . . H5B H 0.3278 0.1075 -0.0517 0.041 Uiso 1 1 calc R . . C6 C 0.3023(5) -0.0283(4) 0.0260(4) 0.0433(13) Uani 1 1 d . . . H6A H 0.3941 -0.0521 0.0219 0.065 Uiso 1 1 calc R . . H6B H 0.2488 -0.0703 -0.0143 0.065 Uiso 1 1 calc R . . H6C H 0.2700 -0.0415 0.0836 0.065 Uiso 1 1 calc R . . Te Te 0.05330(4) 0.2500 0.2500 0.02288(16) Uani 1 2 d S . . N N 0.1561(4) 0.1334(3) 0.0105(2) 0.0276(9) Uani 1 1 d . . . O O -0.0140(3) 0.2072(3) 0.0830(2) 0.0343(8) Uani 1 1 d . . . I I 0.06067(4) 0.48344(3) 0.21110(2) 0.05205(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(3) 0.032(2) 0.025(2) -0.003(2) 0.0033(18) 0.0026(19) C2 0.025(2) 0.025(2) 0.023(2) 0.0030(19) -0.0041(18) 0.0017(19) C3 0.046(3) 0.033(3) 0.023(2) -0.008(2) -0.004(2) -0.005(2) C4 0.121(6) 0.042(3) 0.041(3) 0.005(3) -0.026(4) -0.015(4) C5 0.028(3) 0.041(3) 0.033(2) -0.010(2) 0.008(2) -0.005(2) C6 0.037(3) 0.043(3) 0.050(3) -0.006(3) 0.001(2) 0.005(3) Te 0.0215(2) 0.0303(2) 0.0169(2) -0.00145(17) 0.000 0.000 N 0.030(2) 0.032(2) 0.0217(18) -0.0090(17) 0.0032(17) -0.0016(17) O 0.029(2) 0.045(2) 0.0287(16) -0.0049(15) -0.0053(14) 0.0090(16) I 0.0891(4) 0.0322(2) 0.0349(2) 0.00428(15) 0.00566(18) 0.01322(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 C2 1.515(6) . ? C1 Te 2.145(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O 1.239(6) . ? C2 N 1.333(6) . ? C3 N 1.474(6) . ? C3 C4 1.500(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N 1.472(6) . ? C5 C6 1.512(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? Te C1 2.145(4) 3 ? Te O 2.774(3) . ? Te I 2.8855(4) 3 ? Te I 2.8855(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 C2 C1 Te 102.4(3) . . ? C2 C1 H1A 111.3 . . ? Te C1 H1A 111.3 . . ? C2 C1 H1B 111.3 . . ? Te C1 H1B 111.3 . . ? H1A C1 H1B 109.2 . . ? O C2 N 122.9(4) . . ? O C2 C1 118.0(4) . . ? N C2 C1 119.2(4) . . ? N C3 C4 112.0(4) . . ? N C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N C5 C6 111.4(4) . . ? N C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? N C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1 Te C1 97.5(2) 3 . ? C1 Te O 152.71(14) 3 . ? C1 Te O 55.72(13) . . ? C1 Te I 91.89(13) 3 3 ? C1 Te I 86.14(13) . 3 ? C1 Te I 86.14(13) 3 . ? C1 Te I 91.89(13) . . ? I Te I 177.02(2) 3 . ? C2 N C5 124.1(4) . . ? C2 N C3 119.1(4) . . ? C5 N C3 116.7(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Te C1 C2 O 14.3(5) . . . . ? Te C1 C2 N -166.4(3) . . . . ? C2 C1 Te C1 179.1(4) . . . 3 ? C2 C1 Te I 87.7(3) . . . 3 ? C2 C1 Te I -94.5(3) . . . . ? O C2 N C5 -173.8(4) . . . . ? C1 C2 N C5 6.9(6) . . . . ? O C2 N C3 4.4(7) . . . . ? C1 C2 N C3 -174.9(4) . . . . ? C6 C5 N C2 96.8(5) . . . . ? C6 C5 N C3 -81.5(5) . . . . ? C4 C3 N C2 90.2(6) . . . . ? C4 C3 N C5 -91.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.395 _refine_diff_density_min -1.410 _refine_diff_density_rms 0.121 # Attachment 'CIF-2.cif' data_AKSC_AM3 _database_code_depnum_ccdc_archive 'CCDC 751766' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N2 O2 Te' _chemical_formula_sum 'C18 H20 N2 O2 Te' _chemical_formula_weight 423.96 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' Te Te -0.5308 1.6751 '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/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.8024(2) _cell_length_b 6.8231(2) _cell_length_c 25.2961(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.219(2) _cell_angle_gamma 90.00 _cell_volume 1822.23(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 17292 _cell_measurement_theta_min 4.8051 _cell_measurement_theta_max 32.4710 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 1.643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5385 _exptl_absorpt_correction_T_max 0.6562 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'Oxford Diffraction Gemini' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 25570 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0119 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 4.81 _diffrn_reflns_theta_max 27.99 _reflns_number_total 4355 _reflns_number_gt 3788 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0215P)^2^+1.3249P] 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_number_reflns 4355 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0668 _refine_ls_wR_factor_gt 0.0624 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6833(2) 0.0303(4) 0.17426(10) 0.0422(5) Uani 1 1 d . . . H1A H 0.7119 0.0979 0.2084 0.051 Uiso 1 1 calc R . . H1B H 0.6043 0.0891 0.1557 0.051 Uiso 1 1 calc R . . C2 C 0.6640(2) -0.1856(4) 0.18413(9) 0.0409(5) Uani 1 1 d . . . C3 C 0.5234(3) -0.4461(4) 0.20088(14) 0.0624(7) Uani 1 1 d . . . H3A H 0.4362 -0.4707 0.1846 0.094 Uiso 1 1 calc R . . H3B H 0.5390 -0.4794 0.2386 0.094 Uiso 1 1 calc R . . H3C H 0.5766 -0.5243 0.1833 0.094 Uiso 1 1 calc R . . C4 C 0.4608(2) -0.0974(3) 0.20508(9) 0.0373(5) Uani 1 1 d . . . C5 C 0.3462(3) -0.0797(4) 0.16885(10) 0.0501(6) Uani 1 1 d . . . H5 H 0.3286 -0.1575 0.1380 0.060 Uiso 1 1 calc R . . C6 C 0.2575(3) 0.0544(5) 0.17866(12) 0.0578(7) Uani 1 1 d . . . H6 H 0.1803 0.0674 0.1543 0.069 Uiso 1 1 calc R . . C7 C 0.2839(3) 0.1687(4) 0.22461(13) 0.0579(7) Uani 1 1 d . . . H7 H 0.2245 0.2593 0.2311 0.070 Uiso 1 1 calc R . . C8 C 0.3971(3) 0.1493(4) 0.26070(12) 0.0580(7) Uani 1 1 d . . . H8 H 0.4143 0.2267 0.2917 0.070 Uiso 1 1 calc R . . C9 C 0.4861(2) 0.0153(4) 0.25137(11) 0.0468(6) Uani 1 1 d . . . H9 H 0.5626 0.0012 0.2761 0.056 Uiso 1 1 calc R . . C11 C 0.7491(3) 0.3272(4) 0.08854(10) 0.0492(6) Uani 1 1 d . . . H11A H 0.7386 0.4200 0.1163 0.059 Uiso 1 1 calc R . . H11B H 0.8079 0.3826 0.0685 0.059 Uiso 1 1 calc R . . C12 C 0.6240(2) 0.2903(3) 0.05117(10) 0.0410(5) Uani 1 1 d . . . C13 C 0.5015(2) 0.2329(4) -0.04018(11) 0.0539(6) Uani 1 1 d . . . H13A H 0.4839 0.3327 -0.0675 0.081 Uiso 1 1 calc R . . H13B H 0.4341 0.2286 -0.0208 0.081 Uiso 1 1 calc R . . H13C H 0.5082 0.1082 -0.0569 0.081 Uiso 1 1 calc R . . C14 C 0.7300(2) 0.3028(4) -0.02594(9) 0.0424(5) Uani 1 1 d . . . C15 C 0.8120(3) 0.1477(5) -0.02680(10) 0.0548(7) Uani 1 1 d . . . H15 H 0.7975 0.0281 -0.0116 0.066 Uiso 1 1 calc R . . C16 C 0.9156(3) 0.1710(6) -0.05037(12) 0.0677(9) Uani 1 1 d . . . H16 H 0.9715 0.0673 -0.0503 0.081 Uiso 1 1 calc R . . C17 C 0.9364(3) 0.3459(6) -0.07378(14) 0.0735(9) Uani 1 1 d . . . H17 H 1.0063 0.3616 -0.0894 0.088 Uiso 1 1 calc R . . C18 C 0.8530(4) 0.4976(6) -0.07383(17) 0.0824(11) Uani 1 1 d . . . H18 H 0.8665 0.6158 -0.0900 0.099 Uiso 1 1 calc R . . C19 C 0.7483(3) 0.4781(5) -0.05008(13) 0.0619(7) Uani 1 1 d . . . H19 H 0.6920 0.5815 -0.0505 0.074 Uiso 1 1 calc R . . N1 N 0.55175(19) -0.2382(3) 0.19501(9) 0.0438(4) Uani 1 1 d . . . N2 N 0.62076(19) 0.2777(3) -0.00260(8) 0.0433(4) Uani 1 1 d . . . O1 O 0.74634(18) -0.3066(3) 0.18077(9) 0.0620(5) Uani 1 1 d . . . O2 O 0.52785(17) 0.2706(3) 0.06936(8) 0.0530(4) Uani 1 1 d . . . Te Te 0.823162(15) 0.05336(3) 0.125542(7) 0.05376(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0397(11) 0.0473(13) 0.0437(12) -0.0027(10) 0.0182(10) 0.0061(10) C2 0.0408(11) 0.0450(13) 0.0356(11) 0.0009(10) 0.0050(9) 0.0097(10) C3 0.0720(19) 0.0367(14) 0.081(2) 0.0031(14) 0.0216(16) 0.0011(13) C4 0.0420(11) 0.0331(11) 0.0405(11) 0.0005(9) 0.0167(9) -0.0012(9) C5 0.0518(14) 0.0560(16) 0.0425(13) -0.0038(12) 0.0101(11) 0.0033(12) C6 0.0478(14) 0.0634(18) 0.0634(17) 0.0106(15) 0.0147(12) 0.0116(13) C7 0.0611(16) 0.0458(15) 0.0768(19) 0.0022(14) 0.0371(15) 0.0058(13) C8 0.0681(18) 0.0492(15) 0.0651(17) -0.0175(14) 0.0331(15) -0.0093(13) C9 0.0451(13) 0.0489(14) 0.0484(13) -0.0073(11) 0.0147(10) -0.0081(11) C11 0.0566(14) 0.0507(15) 0.0435(13) -0.0059(11) 0.0175(11) -0.0108(12) C12 0.0478(12) 0.0311(11) 0.0468(12) 0.0009(10) 0.0161(10) 0.0056(9) C13 0.0483(14) 0.0562(16) 0.0541(15) -0.0007(13) 0.0039(11) 0.0036(12) C14 0.0436(12) 0.0486(14) 0.0352(11) -0.0010(10) 0.0091(9) 0.0051(10) C15 0.0596(15) 0.0641(17) 0.0425(13) 0.0089(12) 0.0151(12) 0.0199(14) C16 0.0547(16) 0.101(3) 0.0487(15) 0.0042(17) 0.0147(13) 0.0272(17) C17 0.0539(17) 0.107(3) 0.0642(19) 0.001(2) 0.0239(14) -0.0015(18) C18 0.090(3) 0.076(2) 0.091(3) 0.013(2) 0.040(2) -0.012(2) C19 0.0664(18) 0.0535(17) 0.0704(19) 0.0078(14) 0.0249(15) 0.0060(14) N1 0.0479(11) 0.0357(10) 0.0497(11) -0.0012(9) 0.0145(9) 0.0040(8) N2 0.0432(10) 0.0452(11) 0.0429(10) -0.0005(9) 0.0121(8) 0.0048(9) O1 0.0511(10) 0.0567(12) 0.0787(14) 0.0040(10) 0.0147(10) 0.0227(9) O2 0.0491(9) 0.0565(11) 0.0591(11) 0.0055(9) 0.0239(8) 0.0089(8) Te 0.03674(9) 0.07949(15) 0.04874(10) 0.00416(9) 0.01739(7) 0.01306(8) _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 C2 1.515(4) . ? C1 Te 2.148(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 O1 1.230(3) . ? C2 N1 1.348(3) . ? C3 N1 1.465(3) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C9 1.379(3) . ? C4 C5 1.381(3) . ? C4 N1 1.435(3) . ? C5 C6 1.384(4) . ? C5 H5 0.9300 . ? C6 C7 1.378(4) . ? C6 H6 0.9300 . ? C7 C8 1.369(4) . ? C7 H7 0.9300 . ? C8 C9 1.383(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C11 C12 1.497(4) . ? C11 Te 2.166(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O2 1.229(3) . ? C12 N2 1.356(3) . ? C13 N2 1.462(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C19 1.376(4) . ? C14 C15 1.383(4) . ? C14 N2 1.437(3) . ? C15 C16 1.385(4) . ? C15 H15 0.9300 . ? C16 C17 1.372(5) . ? C16 H16 0.9300 . ? C17 C18 1.372(5) . ? C17 H17 0.9300 . ? C18 C19 1.394(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? O1 Te 3.027(2) . ? 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 C2 C1 Te 107.67(15) . . ? C2 C1 H1A 110.2 . . ? Te C1 H1A 110.2 . . ? C2 C1 H1B 110.2 . . ? Te C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? O1 C2 N1 122.0(2) . . ? O1 C2 C1 121.0(2) . . ? N1 C2 C1 117.0(2) . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C9 C4 C5 120.3(2) . . ? C9 C4 N1 120.2(2) . . ? C5 C4 N1 119.5(2) . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 119.8(3) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C8 C7 C6 120.3(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C4 C9 C8 119.6(3) . . ? C4 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C12 C11 Te 109.25(17) . . ? C12 C11 H11A 109.8 . . ? Te C11 H11A 109.8 . . ? C12 C11 H11B 109.8 . . ? Te C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? O2 C12 N2 121.6(2) . . ? O2 C12 C11 120.2(2) . . ? N2 C12 C11 118.2(2) . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 120.4(2) . . ? C19 C14 N2 119.6(2) . . ? C15 C14 N2 120.0(2) . . ? C14 C15 C16 119.9(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 120.4(3) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 119.3(3) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C19 121.3(3) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C14 C19 C18 118.7(3) . . ? C14 C19 H19 120.7 . . ? C18 C19 H19 120.7 . . ? C2 N1 C4 122.5(2) . . ? C2 N1 C3 119.7(2) . . ? C4 N1 C3 117.7(2) . . ? C12 N2 C14 123.7(2) . . ? C12 N2 C13 119.8(2) . . ? C14 N2 C13 116.4(2) . . ? C1 Te C11 94.05(9) . . ? C1 Te O1 51.75(8) . . ? C11 Te O1 141.91(8) . . ? 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 Te C1 C2 O1 22.7(3) . . . . ? Te C1 C2 N1 -155.30(17) . . . . ? C9 C4 C5 C6 1.2(4) . . . . ? N1 C4 C5 C6 179.3(2) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? C5 C6 C7 C8 -0.3(4) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C5 C4 C9 C8 -1.4(4) . . . . ? N1 C4 C9 C8 -179.5(2) . . . . ? C7 C8 C9 C4 0.8(4) . . . . ? Te C11 C12 O2 78.8(2) . . . . ? Te C11 C12 N2 -100.5(2) . . . . ? C19 C14 C15 C16 2.3(4) . . . . ? N2 C14 C15 C16 178.6(3) . . . . ? C14 C15 C16 C17 -1.2(5) . . . . ? C15 C16 C17 C18 -0.3(5) . . . . ? C16 C17 C18 C19 0.7(6) . . . . ? C15 C14 C19 C18 -1.9(5) . . . . ? N2 C14 C19 C18 -178.2(3) . . . . ? C17 C18 C19 C14 0.4(6) . . . . ? O1 C2 N1 C4 172.8(2) . . . . ? C1 C2 N1 C4 -9.2(3) . . . . ? O1 C2 N1 C3 -2.6(4) . . . . ? C1 C2 N1 C3 175.4(2) . . . . ? C9 C4 N1 C2 -68.1(3) . . . . ? C5 C4 N1 C2 113.7(3) . . . . ? C9 C4 N1 C3 107.3(3) . . . . ? C5 C4 N1 C3 -70.8(3) . . . . ? O2 C12 N2 C14 179.0(2) . . . . ? C11 C12 N2 C14 -1.7(3) . . . . ? O2 C12 N2 C13 -2.1(4) . . . . ? C11 C12 N2 C13 177.2(2) . . . . ? C19 C14 N2 C12 -101.1(3) . . . . ? C15 C14 N2 C12 82.5(3) . . . . ? C19 C14 N2 C13 79.9(3) . . . . ? C15 C14 N2 C13 -96.4(3) . . . . ? C2 C1 Te C11 151.72(16) . . . . ? C12 C11 Te C1 -69.90(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C9 H9 O1 0.93 2.49 3.268(3) 140.8 2_655 C19 H19 O2 0.93 2.53 3.386(4) 152.9 3_665 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.438 _refine_diff_density_min -0.535 _refine_diff_density_rms 0.057 # Attachment 'CIF-2c.cif' data_AKSC_AM2 _database_code_depnum_ccdc_archive 'CCDC 751767' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 I2 N2 O2 Te' _chemical_formula_sum 'C18 H20 I2 N2 O2 Te' _chemical_formula_weight 677.76 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' Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.7610(3) _cell_length_b 20.0422(4) _cell_length_c 11.3681(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.035(3) _cell_angle_gamma 90.00 _cell_volume 2157.57(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8052 _cell_measurement_theta_min 4.5913 _cell_measurement_theta_max 32.5547 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.21 _exptl_crystal_density_diffrn 2.087 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 4.254 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2397 _exptl_absorpt_correction_T_max 0.4687 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'Oxford Diffraction Gemini' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 16624 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.60 _diffrn_reflns_theta_max 26.99 _reflns_number_total 4697 _reflns_number_gt 3361 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0210P)^2^+5.1931P] 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 0.00107(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4697 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0783 _refine_ls_wR_factor_gt 0.0649 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2635(6) 0.9091(2) 0.5332(4) 0.0410(11) Uani 1 1 d . . . H1A H 0.3568 0.9275 0.5664 0.049 Uiso 1 1 calc R . . H1B H 0.1961 0.9325 0.5685 0.049 Uiso 1 1 calc R . . C2 C 0.2612(6) 0.8348(2) 0.5578(5) 0.0465(13) Uani 1 1 d . . . C3 C 0.2919(10) 0.7421(3) 0.6984(7) 0.089(3) Uani 1 1 d . . . H3A H 0.2809 0.7343 0.7789 0.134 Uiso 1 1 calc R . . H3B H 0.3817 0.7252 0.6917 0.134 Uiso 1 1 calc R . . H3C H 0.2178 0.7197 0.6409 0.134 Uiso 1 1 calc R . . C4 C 0.3127(6) 0.8584(3) 0.7759(5) 0.0483(13) Uani 1 1 d . . . C5 C 0.2069(6) 0.9009(3) 0.7933(5) 0.0489(13) Uani 1 1 d . . . H5 H 0.1200 0.9020 0.7372 0.059 Uiso 1 1 calc R . . C6 C 0.2320(7) 0.9416(3) 0.8949(5) 0.0560(15) Uani 1 1 d . . . H6 H 0.1619 0.9707 0.9059 0.067 Uiso 1 1 calc R . . C7 C 0.3577(8) 0.9395(3) 0.9785(6) 0.0636(17) Uani 1 1 d . . . H7 H 0.3734 0.9664 1.0471 0.076 Uiso 1 1 calc R . . C8 C 0.4610(7) 0.8973(4) 0.9606(6) 0.0684(18) Uani 1 1 d . . . H8 H 0.5471 0.8962 1.0178 0.082 Uiso 1 1 calc R . . C9 C 0.4416(7) 0.8564(3) 0.8607(6) 0.0626(17) Uani 1 1 d . . . H9 H 0.5131 0.8280 0.8503 0.075 Uiso 1 1 calc R . . C11 C 0.2037(6) 1.0243(2) 0.3448(4) 0.0371(11) Uani 1 1 d . . . H11A H 0.1309 1.0405 0.3825 0.045 Uiso 1 1 calc R . . H11B H 0.2943 1.0420 0.3886 0.045 Uiso 1 1 calc R . . C12 C 0.1718(5) 1.0435(2) 0.2117(4) 0.0372(11) Uani 1 1 d . . . C13 C 0.1307(7) 1.1255(3) 0.0523(5) 0.0624(17) Uani 1 1 d . . . H13A H 0.1559 1.1710 0.0415 0.094 Uiso 1 1 calc R . . H13B H 0.0306 1.1200 0.0219 0.094 Uiso 1 1 calc R . . H13C H 0.1794 1.0966 0.0087 0.094 Uiso 1 1 calc R . . C14 C 0.2019(6) 1.1617(2) 0.2680(5) 0.0413(12) Uani 1 1 d . . . C15 C 0.3327(6) 1.1675(3) 0.3470(6) 0.0519(14) Uani 1 1 d . . . H15 H 0.4022 1.1360 0.3454 0.062 Uiso 1 1 calc R . . C16 C 0.3614(7) 1.2194(3) 0.4284(6) 0.0676(18) Uani 1 1 d . . . H16 H 0.4490 1.2218 0.4833 0.081 Uiso 1 1 calc R . . C17 C 0.2622(8) 1.2678(3) 0.4293(7) 0.074(2) Uani 1 1 d . . . H17 H 0.2824 1.3033 0.4834 0.089 Uiso 1 1 calc R . . C18 C 0.1318(8) 1.2628(3) 0.3486(7) 0.0720(19) Uani 1 1 d . . . H18 H 0.0635 1.2952 0.3485 0.086 Uiso 1 1 calc R . . C19 C 0.1018(7) 1.2101(3) 0.2680(6) 0.0613(16) Uani 1 1 d . . . H19 H 0.0138 1.2074 0.2137 0.074 Uiso 1 1 calc R . . N1 N 0.2846(5) 0.8144(2) 0.6732(4) 0.0528(12) Uani 1 1 d . . . N2 N 0.1707(5) 1.1085(2) 0.1821(4) 0.0439(10) Uani 1 1 d . . . O1 O 0.2413(5) 0.79594(18) 0.4717(4) 0.0653(12) Uani 1 1 d . . . O2 O 0.1432(4) 0.99897(18) 0.1352(3) 0.0517(9) Uani 1 1 d . . . Te Te 0.20693(3) 0.917686(14) 0.34035(3) 0.03522(10) Uani 1 1 d . . . I1 I 0.50594(4) 0.92946(2) 0.33937(4) 0.05725(13) Uani 1 1 d . . . I2 I -0.08717(4) 0.91745(2) 0.35379(4) 0.06046(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.059(3) 0.031(2) 0.032(2) 0.001(2) 0.010(2) 0.002(2) C2 0.072(4) 0.030(3) 0.041(3) 0.002(2) 0.020(3) 0.009(2) C3 0.165(8) 0.032(3) 0.078(5) 0.017(3) 0.042(5) 0.025(4) C4 0.069(4) 0.042(3) 0.037(3) 0.010(2) 0.018(3) 0.010(3) C5 0.065(4) 0.044(3) 0.040(3) 0.007(2) 0.017(3) 0.013(3) C6 0.076(4) 0.048(3) 0.049(3) 0.003(3) 0.024(3) 0.009(3) C7 0.083(5) 0.065(4) 0.045(3) -0.009(3) 0.020(3) -0.007(3) C8 0.064(4) 0.093(5) 0.046(4) 0.012(3) 0.009(3) -0.011(4) C9 0.063(4) 0.075(4) 0.053(4) 0.012(3) 0.021(3) 0.019(3) C11 0.055(3) 0.027(2) 0.027(2) -0.0028(19) 0.007(2) -0.003(2) C12 0.043(3) 0.035(3) 0.034(3) 0.001(2) 0.011(2) 0.004(2) C13 0.090(5) 0.060(4) 0.036(3) 0.014(3) 0.012(3) 0.010(3) C14 0.052(3) 0.030(2) 0.041(3) 0.007(2) 0.011(2) 0.000(2) C15 0.047(3) 0.040(3) 0.067(4) 0.002(3) 0.011(3) 0.002(2) C16 0.071(4) 0.053(4) 0.074(5) -0.009(3) 0.009(3) -0.008(3) C17 0.097(6) 0.047(4) 0.080(5) -0.020(3) 0.023(4) -0.004(3) C18 0.079(5) 0.044(3) 0.090(5) -0.008(3) 0.016(4) 0.012(3) C19 0.070(4) 0.041(3) 0.069(4) -0.006(3) 0.009(3) 0.012(3) N1 0.090(4) 0.029(2) 0.043(3) 0.0070(19) 0.022(2) 0.015(2) N2 0.064(3) 0.035(2) 0.031(2) 0.0057(18) 0.008(2) 0.0055(19) O1 0.113(4) 0.035(2) 0.049(2) -0.0065(18) 0.022(2) 0.006(2) O2 0.076(3) 0.043(2) 0.0318(19) -0.0062(16) 0.0057(18) 0.0042(18) Te 0.0464(2) 0.02789(16) 0.03057(16) -0.00258(13) 0.00778(13) 0.00216(13) I1 0.0475(2) 0.0732(3) 0.0495(2) -0.01004(19) 0.00864(17) -0.00145(18) I2 0.0533(2) 0.0519(2) 0.0802(3) -0.0214(2) 0.0239(2) -0.00767(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 C1 C2 1.517(6) . ? C1 Te 2.133(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 O1 1.229(6) . ? C2 N1 1.340(6) . ? C3 N1 1.476(7) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C9 1.388(8) . ? C4 C5 1.388(7) . ? C4 N1 1.436(7) . ? C5 C6 1.387(8) . ? C5 H5 0.9300 . ? C6 C7 1.359(9) . ? C6 H6 0.9300 . ? C7 C8 1.368(9) . ? C7 H7 0.9300 . ? C8 C9 1.376(9) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C11 C12 1.518(6) . ? C11 Te 2.138(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O2 1.230(6) . ? C12 N2 1.346(6) . ? C13 N2 1.472(6) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.376(7) . ? C14 C19 1.378(7) . ? C14 N2 1.428(6) . ? C15 C16 1.376(8) . ? C15 H15 0.9300 . ? C16 C17 1.371(9) . ? C16 H16 0.9300 . ? C17 C18 1.380(10) . ? C17 H17 0.9300 . ? C18 C19 1.381(8) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? O1 Te 2.838(4) . ? O2 Te 2.789(4) . ? Te I2 2.9116(5) . ? Te I1 2.9308(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 C2 C1 Te 104.9(3) . . ? C2 C1 H1A 110.8 . . ? Te C1 H1A 110.8 . . ? C2 C1 H1B 110.8 . . ? Te C1 H1B 110.8 . . ? H1A C1 H1B 108.8 . . ? O1 C2 N1 122.8(5) . . ? O1 C2 C1 118.9(5) . . ? N1 C2 C1 118.3(4) . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C9 C4 C5 119.9(5) . . ? C9 C4 N1 120.6(5) . . ? C5 C4 N1 119.4(5) . . ? C6 C5 C4 119.5(6) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C7 C6 C5 120.7(6) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.2(6) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C7 C8 C9 122.1(6) . . ? C7 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? C8 C9 C4 118.4(6) . . ? C8 C9 H9 120.8 . . ? C4 C9 H9 120.8 . . ? C12 C11 Te 103.3(3) . . ? C12 C11 H11A 111.1 . . ? Te C11 H11A 111.1 . . ? C12 C11 H11B 111.1 . . ? Te C11 H11B 111.1 . . ? H11A C11 H11B 109.1 . . ? O2 C12 N2 122.6(4) . . ? O2 C12 C11 118.5(4) . . ? N2 C12 C11 118.8(4) . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 119.1(5) . . ? C15 C14 N2 121.3(5) . . ? C19 C14 N2 119.5(5) . . ? C16 C15 C14 120.5(6) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 120.7(6) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 118.9(6) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? C17 C18 C19 120.6(6) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C14 C19 C18 120.1(6) . . ? C14 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C2 N1 C4 124.2(4) . . ? C2 N1 C3 118.6(5) . . ? C4 N1 C3 117.1(5) . . ? C12 N2 C14 124.3(4) . . ? C12 N2 C13 117.3(4) . . ? C14 N2 C13 118.3(4) . . ? C1 Te C11 93.29(17) . . ? C1 Te O2 148.84(14) . . ? C11 Te O2 55.55(14) . . ? C1 Te O1 54.71(15) . . ? C11 Te O1 147.93(14) . . ? C1 Te I2 87.63(15) . . ? C11 Te I2 88.86(14) . . ? C1 Te I1 90.04(15) . . ? C11 Te I1 86.56(14) . . ? I2 Te I1 174.733(15) . . ? Te I1 I2 171.500(17) . 1_655 ? 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 Te C1 C2 O1 5.6(6) . . . . ? Te C1 C2 N1 -176.0(4) . . . . ? C9 C4 C5 C6 0.9(8) . . . . ? N1 C4 C5 C6 177.5(5) . . . . ? C4 C5 C6 C7 -1.2(9) . . . . ? C5 C6 C7 C8 1.0(10) . . . . ? C6 C7 C8 C9 -0.5(10) . . . . ? C7 C8 C9 C4 0.1(10) . . . . ? C5 C4 C9 C8 -0.3(9) . . . . ? N1 C4 C9 C8 -176.9(5) . . . . ? Te C11 C12 O2 6.4(5) . . . . ? Te C11 C12 N2 -176.0(4) . . . . ? C19 C14 C15 C16 2.6(9) . . . . ? N2 C14 C15 C16 179.3(5) . . . . ? C14 C15 C16 C17 -2.4(10) . . . . ? C15 C16 C17 C18 1.2(11) . . . . ? C16 C17 C18 C19 -0.2(11) . . . . ? C15 C14 C19 C18 -1.6(9) . . . . ? N2 C14 C19 C18 -178.3(6) . . . . ? C17 C18 C19 C14 0.4(11) . . . . ? O1 C2 N1 C4 177.9(6) . . . . ? C1 C2 N1 C4 -0.3(8) . . . . ? O1 C2 N1 C3 2.2(9) . . . . ? C1 C2 N1 C3 -176.0(6) . . . . ? C9 C4 N1 C2 -116.2(6) . . . . ? C5 C4 N1 C2 67.2(8) . . . . ? C9 C4 N1 C3 59.5(8) . . . . ? C5 C4 N1 C3 -117.1(6) . . . . ? O2 C12 N2 C14 179.4(5) . . . . ? C11 C12 N2 C14 1.9(7) . . . . ? O2 C12 N2 C13 1.2(8) . . . . ? C11 C12 N2 C13 -176.3(5) . . . . ? C15 C14 N2 C12 62.6(7) . . . . ? C19 C14 N2 C12 -120.8(6) . . . . ? C15 C14 N2 C13 -119.2(6) . . . . ? C19 C14 N2 C13 57.4(7) . . . . ? C2 C1 Te C11 175.2(4) . . . . ? C2 C1 Te I2 86.5(3) . . . . ? C2 C1 Te I1 -98.3(3) . . . . ? C12 C11 Te C1 177.1(3) . . . . ? C12 C11 Te I2 -95.3(3) . . . . ? C12 C11 Te I1 87.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.259 _refine_diff_density_min -1.178 _refine_diff_density_rms 0.109 # Attachment 'CIF-4b.cif' data_RSC-6 _database_code_depnum_ccdc_archive 'CCDC 751768' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H20 Br2 N2 O4 Te' _chemical_formula_sum 'C12 H20 Br2 N2 O4 Te' _chemical_formula_weight 543.72 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' Br Br -0.2901 2.4595 '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 Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.7035(12) _cell_length_b 12.6321(13) _cell_length_c 9.7267(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.872(8) _cell_angle_gamma 90.00 _cell_volume 1805.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 2888 _cell_measurement_theta_min 5.1006 _cell_measurement_theta_max 32.4467 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.86 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 2.000 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 6.088 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.0775 _exptl_absorpt_correction_T_max 0.4620 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Xcalibur, Ruby, Gemini' _diffrn_measurement_method '\w \ scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 4472 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1556 _reflns_number_gt 1250 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0779P)^2^+194.0444P] 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_number_reflns 1556 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1019 _refine_ls_R_factor_gt 0.0915 _refine_ls_wR_factor_ref 0.2722 _refine_ls_wR_factor_gt 0.2680 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _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 C1 C 0.1026(11) 0.5618(13) 0.737(2) 0.040(4) Uani 1 1 d . . . H1A H 0.1070 0.5201 0.8235 0.048 Uiso 1 1 calc R . . H1B H 0.0888 0.5132 0.6596 0.048 Uiso 1 1 calc R . . C2 C 0.1894(11) 0.6210(14) 0.715(2) 0.040(4) Uani 1 1 d . . . C3 C 0.3545(15) 0.6130(19) 0.678(3) 0.072(7) Uani 1 1 d . . . H3A H 0.3493 0.6911 0.6744 0.086 Uiso 1 1 calc R . . H3B H 0.3946 0.5936 0.7574 0.086 Uiso 1 1 calc R . . C4 C 0.3925(18) 0.574(2) 0.552(4) 0.085(9) Uani 1 1 d . . . H4A H 0.3564 0.6039 0.4735 0.102 Uiso 1 1 calc R . . H4B H 0.4551 0.6024 0.5465 0.102 Uiso 1 1 calc R . . C5 C 0.3085(17) 0.4166(18) 0.555(3) 0.065(7) Uani 1 1 d . . . H5A H 0.3166 0.3388 0.5543 0.078 Uiso 1 1 calc R . . H5B H 0.2672 0.4355 0.4761 0.078 Uiso 1 1 calc R . . C6 C 0.2668(15) 0.4486(17) 0.684(3) 0.067(7) Uani 1 1 d . . . H6A H 0.3029 0.4201 0.7630 0.080 Uiso 1 1 calc R . . H6B H 0.2045 0.4194 0.6869 0.080 Uiso 1 1 calc R . . N N 0.2634(12) 0.5651(13) 0.692(2) 0.061(5) Uani 1 1 d . . . O1 O 0.1891(9) 0.7197(10) 0.7240(16) 0.052(4) Uani 1 1 d . . . O2 O 0.3957(11) 0.4669(14) 0.538(2) 0.078(5) Uani 1 1 d . . . Br Br 0.01879(18) 0.67013(17) 1.0245(2) 0.0594(8) Uani 1 1 d . . . Te Te 0.0000 0.68074(12) 0.7500 0.0364(6) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.031(8) 0.020(9) 0.070(13) -0.005(8) 0.011(8) -0.001(7) C2 0.029(9) 0.027(10) 0.064(12) 0.003(8) 0.008(8) 0.006(7) C3 0.040(12) 0.046(14) 0.13(2) -0.017(14) 0.020(13) -0.009(10) C4 0.060(15) 0.050(15) 0.15(3) 0.005(16) 0.051(17) -0.003(12) C5 0.063(14) 0.039(12) 0.095(18) -0.010(11) 0.031(13) -0.008(10) C6 0.045(12) 0.033(11) 0.12(2) -0.009(12) 0.028(12) -0.006(9) N 0.041(9) 0.028(9) 0.117(16) -0.018(9) 0.031(10) -0.007(7) O1 0.036(7) 0.021(7) 0.098(11) -0.008(7) 0.010(7) -0.001(5) O2 0.049(9) 0.070(12) 0.119(15) -0.015(10) 0.043(9) -0.010(8) Br 0.0829(18) 0.0379(13) 0.0575(14) 0.0000(9) 0.0049(12) 0.0089(10) Te 0.0281(8) 0.0197(8) 0.0620(12) 0.000 0.0080(7) 0.000 _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 C2 1.50(2) . ? C1 Te 2.135(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O1 1.25(2) . ? C2 N 1.32(2) . ? C3 C4 1.44(4) . ? C3 N 1.48(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O2 1.37(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O2 1.44(3) . ? C5 C6 1.47(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N 1.47(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? O1 Te 2.843(13) . ? Br Te 2.678(2) . ? Te C1 2.135(17) 2_556 ? Te Br 2.678(2) 2_556 ? 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 C2 C1 Te 105.3(11) . . ? C2 C1 H1A 110.7 . . ? Te C1 H1A 110.7 . . ? C2 C1 H1B 110.7 . . ? Te C1 H1B 110.7 . . ? H1A C1 H1B 108.8 . . ? O1 C2 N 123.2(17) . . ? O1 C2 C1 118.9(15) . . ? N C2 C1 117.9(16) . . ? C4 C3 N 109(2) . . ? C4 C3 H3A 110.0 . . ? N C3 H3A 110.0 . . ? C4 C3 H3B 110.0 . . ? N C3 H3B 110.0 . . ? H3A C3 H3B 108.3 . . ? O2 C4 C3 116(2) . . ? O2 C4 H4A 108.3 . . ? C3 C4 H4A 108.3 . . ? O2 C4 H4B 108.3 . . ? C3 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? O2 C5 C6 112(2) . . ? O2 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? O2 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C5 C6 N 110(2) . . ? C5 C6 H6A 109.7 . . ? N C6 H6A 109.7 . . ? C5 C6 H6B 109.7 . . ? N C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C2 N C6 124.9(17) . . ? C2 N C3 123.4(17) . . ? C6 N C3 111.7(17) . . ? C4 O2 C5 113.1(18) . . ? C1 Te C1 90.6(9) 2_556 . ? C1 Te Br 88.4(6) 2_556 2_556 ? C1 Te Br 87.6(6) . 2_556 ? C1 Te Br 87.6(6) 2_556 . ? C1 Te Br 88.4(6) . . ? Br Te Br 174.26(11) 2_556 . ? C1 Te O1 145.2(5) 2_556 . ? C1 Te O1 54.7(5) . . ? Br Te O1 89.4(3) 2_556 . ? Br Te O1 91.6(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 Te C1 C2 O1 8(2) . . . . ? Te C1 C2 N -174.5(17) . . . . ? N C3 C4 O2 -54(4) . . . . ? O2 C5 C6 N 53(3) . . . . ? O1 C2 N C6 179(2) . . . . ? C1 C2 N C6 2(3) . . . . ? O1 C2 N C3 1(4) . . . . ? C1 C2 N C3 -176(2) . . . . ? C5 C6 N C2 127(2) . . . . ? C5 C6 N C3 -55(3) . . . . ? C4 C3 N C2 -128(3) . . . . ? C4 C3 N C6 54(3) . . . . ? C3 C4 O2 C5 54(4) . . . . ? C6 C5 O2 C4 -52(3) . . . . ? C2 C1 Te C1 175.6(17) . . . 2_556 ? C2 C1 Te Br 87.3(13) . . . 2_556 ? C2 C1 Te Br -96.8(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1B Br 0.99 2.84 3.772(18) 157.2 6_565 C4 H4B O2 0.99 2.52 3.30(3) 135.6 5_666 C6 H6A O1 0.99 2.54 3.09(3) 115.2 4_546 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 4.314 _refine_diff_density_min -1.743 _refine_diff_density_rms 0.290 # Attachment 'CIF-5b.cif' data_POR8 _database_code_depnum_ccdc_archive 'CCDC 751769' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H23 Br2 N O Te' _chemical_formula_sum 'C15 H23 Br2 N O Te' _chemical_formula_weight 520.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Te Te -0.1759 6.3531 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8137(3) _cell_length_b 16.9123(3) _cell_length_c 18.3227(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3660.82(15) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 16907 _cell_measurement_theta_min 4.4359 _cell_measurement_theta_max 77.3525 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.77 _exptl_crystal_size_mid 0.67 _exptl_crystal_size_min 0.38 _exptl_crystal_density_diffrn 1.890 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 17.907 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.0255 _exptl_absorpt_correction_T_max 0.0560 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 30294 _diffrn_reflns_av_R_equivalents 0.1251 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.83 _diffrn_reflns_theta_max 77.92 _reflns_number_total 3882 _reflns_number_gt 3470 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0925P)^2^+2.8690P] 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 0.00088(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3882 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1356 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4824(4) 0.6555(3) 0.4141(3) 0.0398(10) Uani 1 1 d . . . H1A H 0.4482 0.6166 0.4462 0.048 Uiso 1 1 calc R . . H1B H 0.4520 0.7073 0.4255 0.048 Uiso 1 1 calc R . . C2 C 0.4644(4) 0.6345(3) 0.3345(2) 0.0415(9) Uani 1 1 d . . . C3 C 0.3567(6) 0.5743(4) 0.2376(3) 0.0599(14) Uani 1 1 d . . . H3A H 0.3855 0.6176 0.2083 0.072 Uiso 1 1 calc R . . H3B H 0.2762 0.5695 0.2281 0.072 Uiso 1 1 calc R . . C4 C 0.4149(8) 0.4989(5) 0.2152(4) 0.085(2) Uani 1 1 d . . . H4A H 0.4954 0.5055 0.2191 0.127 Uiso 1 1 calc R . . H4B H 0.3954 0.4865 0.1656 0.127 Uiso 1 1 calc R . . H4C H 0.3909 0.4566 0.2466 0.127 Uiso 1 1 calc R . . C5 C 0.2961(5) 0.5521(3) 0.3670(3) 0.0545(12) Uani 1 1 d . . . H5A H 0.2770 0.5002 0.3481 0.065 Uiso 1 1 calc R . . H5B H 0.3339 0.5449 0.4135 0.065 Uiso 1 1 calc R . . C6 C 0.1913(7) 0.5978(5) 0.3782(5) 0.086(2) Uani 1 1 d . . . H6A H 0.2083 0.6452 0.4049 0.129 Uiso 1 1 calc R . . H6B H 0.1380 0.5666 0.4052 0.129 Uiso 1 1 calc R . . H6C H 0.1593 0.6115 0.3317 0.129 Uiso 1 1 calc R . . C11 C 0.7081(4) 0.65234(19) 0.5343(2) 0.0307(8) Uani 1 1 d . . . C12 C 0.8200(4) 0.6273(2) 0.5461(2) 0.0346(8) Uani 1 1 d . . . C13 C 0.8629(4) 0.6339(3) 0.6164(3) 0.0433(9) Uani 1 1 d . . . H13 H 0.9368 0.6174 0.6249 0.052 Uiso 1 1 calc R . . C14 C 0.8011(5) 0.6636(3) 0.6744(3) 0.0438(10) Uani 1 1 d . . . C15 C 0.6902(5) 0.6865(3) 0.6604(2) 0.0426(10) Uani 1 1 d . . . H15 H 0.6466 0.7053 0.6990 0.051 Uiso 1 1 calc R . . C16 C 0.6413(4) 0.6825(2) 0.5914(2) 0.0345(8) Uani 1 1 d . . . C17 C 0.8950(4) 0.5929(3) 0.4877(3) 0.0471(11) Uani 1 1 d . . . H17A H 0.9704 0.5867 0.5064 0.071 Uiso 1 1 calc R . . H17B H 0.8964 0.6277 0.4463 0.071 Uiso 1 1 calc R . . H17C H 0.8661 0.5423 0.4730 0.071 Uiso 1 1 calc R . . C18 C 0.8527(7) 0.6709(5) 0.7491(3) 0.0725(19) Uani 1 1 d . . . H18A H 0.8413 0.6226 0.7756 0.109 Uiso 1 1 calc R . . H18B H 0.8175 0.7138 0.7749 0.109 Uiso 1 1 calc R . . H18C H 0.9324 0.6810 0.7446 0.109 Uiso 1 1 calc R . . C19 C 0.5223(5) 0.7114(3) 0.5821(2) 0.0454(11) Uani 1 1 d . . . H19A H 0.4724 0.6670 0.5762 0.068 Uiso 1 1 calc R . . H19B H 0.5179 0.7446 0.5398 0.068 Uiso 1 1 calc R . . H19C H 0.5002 0.7410 0.6245 0.068 Uiso 1 1 calc R . . N N 0.3743(4) 0.5922(3) 0.3153(2) 0.0493(10) Uani 1 1 d . . . O O 0.5356(4) 0.6592(2) 0.2909(2) 0.0601(10) Uani 1 1 d . . . Br1 Br 0.63530(7) 0.49611(3) 0.42097(3) 0.0539(2) Uani 1 1 d . . . Br2 Br 0.67370(5) 0.81012(3) 0.42613(3) 0.0510(2) Uani 1 1 d . . . Te Te 0.66252(2) 0.653991(14) 0.422152(13) 0.03075(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.034(2) 0.044(3) 0.041(2) -0.0014(16) -0.0011(17) -0.0058(17) C2 0.045(2) 0.043(2) 0.036(2) 0.0041(18) -0.0025(17) -0.0015(19) C3 0.069(3) 0.071(4) 0.039(3) -0.001(2) -0.013(2) -0.008(3) C4 0.113(7) 0.072(4) 0.069(4) -0.014(3) -0.002(4) -0.002(4) C5 0.066(3) 0.046(2) 0.052(3) 0.007(2) -0.007(2) -0.014(2) C6 0.090(5) 0.068(4) 0.099(6) 0.000(4) 0.026(4) 0.012(4) C11 0.039(2) 0.0221(16) 0.0312(19) -0.0021(12) 0.0044(15) -0.0017(13) C12 0.0397(19) 0.0291(19) 0.035(2) -0.0027(15) 0.0032(16) -0.0026(15) C13 0.046(2) 0.040(2) 0.043(2) 0.0033(19) -0.007(2) -0.0075(19) C14 0.060(3) 0.041(2) 0.031(2) 0.0050(16) -0.004(2) -0.013(2) C15 0.065(3) 0.036(2) 0.0267(19) 0.0004(15) 0.0075(19) -0.008(2) C16 0.045(2) 0.0255(18) 0.0336(19) -0.0021(15) 0.0088(17) -0.0029(16) C17 0.040(2) 0.052(3) 0.049(3) -0.010(2) 0.0058(18) 0.0076(19) C18 0.087(5) 0.095(5) 0.035(3) 0.002(3) -0.015(3) -0.018(4) C19 0.049(3) 0.046(3) 0.041(2) -0.0040(17) 0.0142(18) 0.006(2) N 0.055(2) 0.056(2) 0.038(2) 0.0047(17) -0.0100(17) -0.012(2) O 0.067(3) 0.074(3) 0.040(2) 0.0059(16) 0.0042(17) -0.0198(19) Br1 0.0773(4) 0.0283(3) 0.0561(4) -0.00786(18) -0.0007(2) -0.0014(2) Br2 0.0615(4) 0.0305(3) 0.0610(4) 0.00816(19) 0.0104(2) -0.0070(2) Te 0.0379(2) 0.0288(2) 0.0256(2) -0.00110(7) 0.00505(7) -0.00143(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 C1 C2 1.518(6) . ? C1 Te 2.133(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 O 1.233(6) . ? C2 N 1.329(6) . ? C3 N 1.471(6) . ? C3 C4 1.505(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.474(9) . ? C5 N 1.487(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C11 C12 1.404(6) . ? C11 C16 1.406(6) . ? C11 Te 2.125(4) . ? C12 C13 1.388(7) . ? C12 C17 1.507(6) . ? C13 C14 1.384(7) . ? C13 H13 0.9300 . ? C14 C15 1.390(8) . ? C14 C18 1.504(7) . ? C15 C16 1.392(6) . ? C15 H15 0.9300 . ? C16 C19 1.498(7) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? O Te 2.836(4) . ? Br1 Te 2.6895(6) . ? Br2 Te 2.6448(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 C2 C1 Te 101.7(3) . . ? C2 C1 H1A 111.4 . . ? Te C1 H1A 111.4 . . ? C2 C1 H1B 111.4 . . ? Te C1 H1B 111.4 . . ? H1A C1 H1B 109.3 . . ? O C2 N 123.9(5) . . ? O C2 C1 116.7(4) . . ? N C2 C1 119.5(4) . . ? N C3 C4 112.0(5) . . ? N C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 N 111.8(5) . . ? C6 C5 H5A 109.3 . . ? N C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? N C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C11 C16 121.6(4) . . ? C12 C11 Te 113.0(3) . . ? C16 C11 Te 124.9(3) . . ? C13 C12 C11 117.5(4) . . ? C13 C12 C17 118.4(4) . . ? C11 C12 C17 124.1(4) . . ? C14 C13 C12 123.3(5) . . ? C14 C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? C13 C14 C15 117.2(4) . . ? C13 C14 C18 121.0(6) . . ? C15 C14 C18 121.8(5) . . ? C14 C15 C16 123.0(4) . . ? C14 C15 H15 118.5 . . ? C16 C15 H15 118.5 . . ? C15 C16 C11 117.4(4) . . ? C15 C16 C19 118.4(4) . . ? C11 C16 C19 124.1(4) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C2 N C3 118.7(4) . . ? C2 N C5 125.1(4) . . ? C3 N C5 115.7(4) . . ? C11 Te C1 108.64(17) . . ? C11 Te Br2 88.50(9) . . ? C1 Te Br2 92.29(12) . . ? C11 Te Br1 91.43(9) . . ? C1 Te Br1 83.80(12) . . ? C11 Te O 162.72(14) . . ? C1 Te O 54.11(16) . . ? Br2 Te Br1 175.85(2) . . ? 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 Te C1 C2 O -34.3(5) . . . . ? Te C1 C2 N 146.5(4) . . . . ? C16 C11 C12 C13 -0.4(6) . . . . ? Te C11 C12 C13 171.9(3) . . . . ? C16 C11 C12 C17 178.6(4) . . . . ? Te C11 C12 C17 -9.2(5) . . . . ? C11 C12 C13 C14 -0.1(6) . . . . ? C17 C12 C13 C14 -179.2(4) . . . . ? C12 C13 C14 C15 1.1(7) . . . . ? C12 C13 C14 C18 -178.7(5) . . . . ? C13 C14 C15 C16 -1.7(7) . . . . ? C18 C14 C15 C16 178.1(5) . . . . ? C14 C15 C16 C11 1.2(6) . . . . ? C14 C15 C16 C19 -177.9(4) . . . . ? C12 C11 C16 C15 -0.2(6) . . . . ? Te C11 C16 C15 -171.4(3) . . . . ? C12 C11 C16 C19 178.9(4) . . . . ? Te C11 C16 C19 7.6(6) . . . . ? O C2 N C3 -0.8(8) . . . . ? C1 C2 N C3 178.4(5) . . . . ? O C2 N C5 170.9(5) . . . . ? C1 C2 N C5 -9.9(8) . . . . ? C4 C3 N C2 88.8(7) . . . . ? C4 C3 N C5 -83.7(7) . . . . ? C6 C5 N C2 100.6(7) . . . . ? C6 C5 N C3 -87.5(7) . . . . ? C12 C11 Te C1 161.7(3) . . . . ? C16 C11 Te C1 -26.4(3) . . . . ? C12 C11 Te Br2 -106.4(3) . . . . ? C16 C11 Te Br2 65.6(3) . . . . ? C12 C11 Te Br1 77.8(3) . . . . ? C16 C11 Te Br1 -110.3(3) . . . . ? C2 C1 Te C11 -165.5(3) . . . . ? C2 C1 Te Br2 105.4(3) . . . . ? C2 C1 Te Br1 -76.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 77.92 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.800 _refine_diff_density_min -1.955 _refine_diff_density_rms 0.233 # Attachment 'CIF-6b.cif' data_POR12 _database_code_depnum_ccdc_archive 'CCDC 751770' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 Br2 N O Te' _chemical_formula_sum 'C16 H19 Br2 N O Te' _chemical_formula_weight 528.74 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' Br Br -0.2901 2.4595 '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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.9043(3) _cell_length_b 18.3181(6) _cell_length_c 10.0574(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.856(3) _cell_angle_gamma 90.00 _cell_volume 1755.27(9) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 6159 _cell_measurement_theta_min 4.7462 _cell_measurement_theta_max 32.6498 _exptl_crystal_description Plate _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 2.001 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 6.246 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1535 _exptl_absorpt_correction_T_max 0.4348 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 ; Goniometer Xcalibur, detector: Ruby (Gemini Mo) ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 9908 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.76 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4188 _reflns_number_gt 3221 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0723P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0025(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4188 _refine_ls_number_parameters 189 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1103 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4256(5) 0.7085(3) 0.4356(5) 0.0225(12) Uani 1 1 d . . . H1A H 0.4108 0.7167 0.5279 0.027 Uiso 1 1 calc R . . H1B H 0.5021 0.6725 0.4439 0.027 Uiso 1 1 calc RD . . C2 C 0.4584(5) 0.7790(3) 0.3740(5) 0.0172(10) Uani 1 1 d . A . C3 C 0.5897(6) 0.8903(3) 0.3902(5) 0.0272(11) Uani 1 1 d . A . H3A H 0.6353 0.9220 0.4694 0.033 Uiso 1 1 calc R . . H3B H 0.4969 0.9118 0.3446 0.033 Uiso 1 1 calc R . . C4 C 0.6779(6) 0.8910(4) 0.2885(6) 0.0379(13) Uani 1 1 d . . . H4A H 0.7708 0.8706 0.3327 0.057 Uiso 1 1 calc R . . H4B H 0.6882 0.9414 0.2598 0.057 Uiso 1 1 calc R . . H4C H 0.6319 0.8617 0.2074 0.057 Uiso 1 1 calc R . . C5 C 0.6554(8) 0.7999(5) 0.5812(8) 0.0272(11) Uani 0.711(8) 1 d PD A 1 H5A H 0.6027 0.7676 0.6282 0.033 Uiso 0.711(8) 1 calc PR A 1 H5B H 0.6810 0.8448 0.6371 0.033 Uiso 0.711(8) 1 calc PR A 1 C6 C 0.7856(10) 0.7620(5) 0.5692(9) 0.0379(13) Uani 0.711(8) 1 d PD A 1 H6A H 0.7596 0.7197 0.5078 0.057 Uiso 0.711(8) 1 calc PR A 1 H6B H 0.8404 0.7456 0.6608 0.057 Uiso 0.711(8) 1 calc PR A 1 H6C H 0.8420 0.7958 0.5310 0.057 Uiso 0.711(8) 1 calc PR A 1 C5' C 0.7055(19) 0.7729(12) 0.5342(16) 0.0272(6) Uani 0.289(8) 1 d PD A 2 H5A' H 0.6888 0.7196 0.5268 0.033 Uiso 0.289(8) 1 calc PRD A 2 H5B' H 0.7902 0.7846 0.5041 0.033 Uiso 0.289(8) 1 calc PR A 2 C6' C 0.720(2) 0.7995(14) 0.6787(19) 0.0379(17) Uani 0.289(8) 1 d PD A 2 H6A' H 0.6958 0.8515 0.6763 0.057 Uiso 0.289(8) 1 calc PR A 2 H6B' H 0.8165 0.7924 0.7350 0.057 Uiso 0.289(8) 1 calc PR A 2 H6C' H 0.6558 0.7719 0.7191 0.057 Uiso 0.289(8) 1 calc PR A 2 C11 C 0.2112(5) 0.5737(3) 0.3911(5) 0.0170(10) Uani 1 1 d . . . C12 C 0.2986(5) 0.5548(3) 0.5181(5) 0.0244(12) Uani 1 1 d . . . H12 H 0.3719 0.5868 0.5640 0.029 Uiso 1 1 calc R . . C13 C 0.2797(6) 0.4882(3) 0.5802(5) 0.0257(12) Uani 1 1 d . . . H13 H 0.3412 0.4753 0.6673 0.031 Uiso 1 1 calc R . . C14 C 0.1739(6) 0.4418(3) 0.5165(5) 0.0231(11) Uani 1 1 d . . . H14 H 0.1618 0.3972 0.5599 0.028 Uiso 1 1 calc R . . C19 C 0.0822(5) 0.4599(3) 0.3863(5) 0.0184(10) Uani 1 1 d . . . C15 C -0.0289(5) 0.4115(3) 0.3183(5) 0.0225(11) Uani 1 1 d . . . H15 H -0.0417 0.3668 0.3613 0.027 Uiso 1 1 calc R . . C16 C -0.1171(5) 0.4293(3) 0.1915(5) 0.0245(12) Uani 1 1 d . . . H16 H -0.1916 0.3973 0.1480 0.029 Uiso 1 1 calc R . . C17 C -0.0972(5) 0.4945(3) 0.1262(5) 0.0209(11) Uani 1 1 d . . . H17 H -0.1565 0.5054 0.0369 0.025 Uiso 1 1 calc R . . C18 C 0.0064(5) 0.5427(3) 0.1893(5) 0.0181(10) Uani 1 1 d . . . H18 H 0.0165 0.5873 0.1447 0.022 Uiso 1 1 calc R . . C20 C 0.0990(5) 0.5263(3) 0.3210(4) 0.0148(10) Uani 1 1 d . . . O O 0.3801(4) 0.7988(2) 0.2627(3) 0.0241(8) Uani 1 1 d . . . N N 0.5677(5) 0.8185(3) 0.4432(5) 0.0344(13) Uani 1 1 d . . . Br1 Br 0.39195(5) 0.59793(3) 0.15708(5) 0.02560(17) Uani 1 1 d . . . Br2 Br 0.09005(5) 0.74232(3) 0.43711(5) 0.02463(16) Uani 1 1 d . . . Te Te 0.23673(3) 0.672429(19) 0.29080(3) 0.01553(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.021(3) 0.031(4) 0.014(2) -0.001(2) 0.0006(18) -0.009(2) C2 0.021(2) 0.017(3) 0.014(2) -0.0023(19) 0.0057(18) -0.006(2) C3 0.036(2) 0.025(3) 0.020(2) -0.0043(19) 0.0077(18) -0.015(2) C4 0.033(3) 0.041(4) 0.042(3) 0.006(2) 0.015(2) -0.004(2) C5 0.036(2) 0.025(3) 0.020(2) -0.0043(19) 0.0077(18) -0.015(2) C6 0.033(3) 0.041(4) 0.042(3) 0.006(2) 0.015(2) -0.004(2) C5' 0.0362(10) 0.0250(5) 0.0205(9) -0.004(4) 0.0077(19) -0.0148(12) C6' 0.033(4) 0.0413(19) 0.0417(12) 0.0057(16) 0.015(2) -0.0042(14) C11 0.024(2) 0.010(3) 0.019(2) 0.0041(19) 0.0077(19) -0.0022(19) C12 0.023(3) 0.027(4) 0.018(2) 0.003(2) -0.002(2) -0.005(2) C13 0.031(3) 0.025(4) 0.016(2) 0.008(2) -0.001(2) 0.002(2) C14 0.036(3) 0.010(3) 0.025(3) 0.008(2) 0.011(2) 0.004(2) C19 0.021(2) 0.015(3) 0.022(2) -0.001(2) 0.0107(19) 0.001(2) C15 0.029(3) 0.012(3) 0.029(3) 0.001(2) 0.014(2) -0.007(2) C16 0.020(2) 0.021(3) 0.035(3) -0.007(2) 0.010(2) -0.007(2) C17 0.018(2) 0.023(3) 0.020(2) -0.003(2) 0.0023(18) 0.000(2) C18 0.021(2) 0.014(3) 0.019(2) 0.000(2) 0.0048(18) -0.002(2) C20 0.017(2) 0.011(3) 0.017(2) -0.0007(19) 0.0061(17) -0.0007(18) O 0.0224(19) 0.024(2) 0.0219(18) 0.0050(16) -0.0010(14) -0.0064(15) N 0.032(3) 0.042(4) 0.023(2) 0.009(2) -0.003(2) -0.019(2) Br1 0.0245(3) 0.0306(4) 0.0218(3) -0.0007(2) 0.0066(2) -0.0031(2) Br2 0.0296(3) 0.0190(4) 0.0260(3) 0.0012(2) 0.0088(2) -0.0018(2) Te 0.01672(18) 0.0160(2) 0.01147(18) 0.00260(12) -0.00018(11) -0.00555(12) _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 C2 1.505(7) . ? C1 Te 2.137(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O 1.230(6) . ? C2 N 1.330(6) . ? C3 N 1.457(7) . ? C3 C4 1.516(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N 1.462(9) . ? C5 C6 1.499(11) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C5' C6' 1.502(17) . ? C5' N 1.65(2) . ? C5' H5A' 0.9900 . ? C5' H5B' 0.9900 . ? C6' H6A' 0.9800 . ? C6' H6B' 0.9800 . ? C6' H6C' 0.9800 . ? C11 C12 1.378(6) . ? C11 C20 1.435(7) . ? C11 Te 2.118(5) . ? C12 C13 1.406(7) . ? C12 H12 0.9500 . ? C13 C14 1.365(7) . ? C13 H13 0.9500 . ? C14 C19 1.414(7) . ? C14 H14 0.9500 . ? C19 C20 1.414(7) . ? C19 C15 1.432(7) . ? C15 C16 1.374(7) . ? C15 H15 0.9500 . ? C16 C17 1.402(8) . ? C16 H16 0.9500 . ? C17 C18 1.371(7) . ? C17 H17 0.9500 . ? C18 C20 1.422(6) . ? C18 H18 0.9500 . ? O Te 2.770(4) . ? Br1 Te 2.6766(6) . ? Br2 Te 2.6615(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 C2 C1 Te 103.4(3) . . ? C2 C1 H1A 111.1 . . ? Te C1 H1A 111.1 . . ? C2 C1 H1B 111.1 . . ? Te C1 H1B 111.1 . . ? H1A C1 H1B 109.0 . . ? O C2 N 122.4(5) . . ? O C2 C1 118.3(4) . . ? N C2 C1 119.2(4) . . ? N C3 C4 115.2(5) . . ? N C3 H3A 108.5 . . ? C4 C3 H3A 108.5 . . ? N C3 H3B 108.5 . . ? C4 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N C5 C6 109.4(7) . . ? N C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? N C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? C6' C5' N 102.5(16) . . ? C6' C5' H5A' 111.3 . . ? N C5' H5A' 111.3 . . ? C6' C5' H5B' 111.3 . . ? N C5' H5B' 111.3 . . ? H5A' C5' H5B' 109.2 . . ? C5' C6' H6A' 109.5 . . ? C5' C6' H6B' 109.5 . . ? H6A' C6' H6B' 109.5 . . ? C5' C6' H6C' 109.5 . . ? H6A' C6' H6C' 109.5 . . ? H6B' C6' H6C' 109.5 . . ? C12 C11 C20 120.6(5) . . ? C12 C11 Te 122.0(4) . . ? C20 C11 Te 117.4(3) . . ? C11 C12 C13 120.3(5) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 120.6(5) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C19 120.4(5) . . ? C13 C14 H14 119.8 . . ? C19 C14 H14 119.8 . . ? C14 C19 C20 120.3(5) . . ? C14 C19 C15 120.9(5) . . ? C20 C19 C15 118.9(4) . . ? C16 C15 C19 120.5(5) . . ? C16 C15 H15 119.8 . . ? C19 C15 H15 119.8 . . ? C15 C16 C17 120.1(5) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 C16 121.0(5) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C20 120.4(5) . . ? C17 C18 H18 119.8 . . ? C20 C18 H18 119.8 . . ? C19 C20 C18 119.1(4) . . ? C19 C20 C11 117.8(4) . . ? C18 C20 C11 123.1(5) . . ? C2 N C3 118.8(4) . . ? C2 N C5 123.8(5) . . ? C3 N C5 116.7(5) . . ? C2 N C5' 116.5(7) . . ? C3 N C5' 118.5(7) . . ? C11 Te C1 97.8(2) . . ? C11 Te Br2 89.61(13) . . ? C1 Te Br2 89.03(15) . . ? C11 Te Br1 87.92(13) . . ? C1 Te Br1 89.07(15) . . ? Br2 Te Br1 176.658(19) . . ? C11 Te O 153.23(15) . . ? C1 Te O 55.50(17) . . ? Br2 Te O 91.55(8) . . ? Br1 Te O 89.65(8) . . ? 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 Te C1 C2 O -1.6(5) . . . . ? Te C1 C2 N 176.4(4) . . . . ? C20 C11 C12 C13 0.6(8) . . . . ? Te C11 C12 C13 -178.9(4) . . . . ? C11 C12 C13 C14 -0.8(8) . . . . ? C12 C13 C14 C19 0.6(8) . . . . ? C13 C14 C19 C20 -0.2(7) . . . . ? C13 C14 C19 C15 179.8(5) . . . . ? C14 C19 C15 C16 -179.7(5) . . . . ? C20 C19 C15 C16 0.3(7) . . . . ? C19 C15 C16 C17 1.2(8) . . . . ? C15 C16 C17 C18 -2.4(8) . . . . ? C16 C17 C18 C20 2.0(8) . . . . ? C14 C19 C20 C18 179.2(4) . . . . ? C15 C19 C20 C18 -0.8(7) . . . . ? C14 C19 C20 C11 0.1(7) . . . . ? C15 C19 C20 C11 -179.9(4) . . . . ? C17 C18 C20 C19 -0.4(7) . . . . ? C17 C18 C20 C11 178.7(5) . . . . ? C12 C11 C20 C19 -0.3(7) . . . . ? Te C11 C20 C19 179.2(3) . . . . ? C12 C11 C20 C18 -179.4(5) . . . . ? Te C11 C20 C18 0.1(6) . . . . ? O C2 N C3 4.5(8) . . . . ? C1 C2 N C3 -173.4(5) . . . . ? O C2 N C5 174.3(6) . . . . ? C1 C2 N C5 -3.6(9) . . . . ? O C2 N C5' -147.4(8) . . . . ? C1 C2 N C5' 34.6(9) . . . . ? C4 C3 N C2 -88.8(7) . . . . ? C4 C3 N C5 100.6(7) . . . . ? C4 C3 N C5' 62.6(9) . . . . ? C6 C5 N C2 98.5(8) . . . . ? C6 C5 N C3 -91.5(7) . . . . ? C6 C5 N C5' 10.6(12) . . . . ? C6' C5' N C2 -119.7(12) . . . . ? C6' C5' N C3 88.3(13) . . . . ? C6' C5' N C5 -7.8(11) . . . . ? C12 C11 Te C1 4.9(5) . . . . ? C20 C11 Te C1 -174.6(4) . . . . ? C12 C11 Te Br2 -84.0(4) . . . . ? C20 C11 Te Br2 96.5(4) . . . . ? C12 C11 Te Br1 93.7(4) . . . . ? C20 C11 Te Br1 -85.8(4) . . . . ? C2 C1 Te C11 178.7(3) . . . . ? C2 C1 Te Br2 -91.8(3) . . . . ? C2 C1 Te Br1 91.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1A O 0.99 2.48 3.443(6) 164.7 4_576 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.057 _refine_diff_density_min -2.059 _refine_diff_density_rms 0.244