#------------------------------------------------------------------------------ #$Date: 2013-12-28 07:07:06 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91932 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/76/1507697.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1507697 loop_ _publ_author_name 'Olszewska, Teresa' 'Nowak, El\.zbieta' 'Gdaniec, Maria' 'Po\/lo\'nski, Tadeusz' _publ_section_title ; Helicity Discrimination in Diaryl Dichalcogenides Generated by Inclusion Complexation with Chiral Hosts ; _journal_issue 10 _journal_name_full 'Organic Letters' _journal_page_first 2568 _journal_volume 14 _journal_year 2012 _chemical_absolute_configuration syn _chemical_formula_moiety '2(C33 H32 O4), C10 H8 N2 Te2' _chemical_formula_sum 'C76 H72 N2 O8 Te2' _chemical_formula_weight 1396.56 _chemical_name_systematic ; ? ; _space_group_IT_number 151 _symmetry_cell_setting trigonal _symmetry_space_group_name_Hall 'P 31 2 (0 0 4)' _symmetry_space_group_name_H-M 'P 31 1 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_formula_units_Z 3 _cell_length_a 9.4185(2) _cell_length_b 9.4185(2) _cell_length_c 62.497(2) _cell_measurement_reflns_used 17549 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 27.72 _cell_measurement_theta_min 2.81 _cell_volume 4801.2(2) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.8 ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.8 ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.8 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.961 _diffrn_measured_fraction_theta_max 0.961 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur E' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 80 _diffrn_reflns_limit_l_min -79 _diffrn_reflns_number 55633 _diffrn_reflns_theta_full 27.78 _diffrn_reflns_theta_max 27.78 _diffrn_reflns_theta_min 2.82 _exptl_absorpt_coefficient_mu 0.971 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.737 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.8 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour violet _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2130 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.432 _refine_diff_density_min -0.645 _refine_diff_density_rms 0.070 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 397 _refine_ls_number_reflns 7203 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.154 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0535 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0262P)^2^+8.3655P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1072 _refine_ls_wR_factor_ref 0.1094 _reflns_number_gt 6678 _reflns_number_total 7203 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ol300870s_si_002.cif _[local]_cod_data_source_block 5-6a _cod_database_code 1507697 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-y, -x, -z+2/3' 'x, x-y, -z' '-x+y, y, -z+1/3' 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 O11 O 0.5833(4) 0.4836(4) 0.12405(5) 0.0370(7) Uani 1 1 d . O21 O 0.5125(4) 0.4063(4) 0.05617(5) 0.0368(7) Uani 1 1 d . H21O H 0.5196 0.4138 0.0425 0.055 Uiso 1 1 d R O31 O 0.4459(4) 0.5762(4) 0.10419(5) 0.0378(8) Uani 1 1 d . O41 O 0.6480(4) 0.2685(5) 0.08036(5) 0.0423(8) Uani 1 1 d . H41O H 0.6181 0.3080 0.0700 0.063 Uiso 1 1 d R C21 C 0.5398(6) 0.6071(6) 0.12338(7) 0.0364(11) Uani 1 1 d . C41 C 0.4709(5) 0.4684(5) 0.09099(7) 0.0314(9) Uani 1 1 d . H41 H 0.3696 0.3618 0.0909 0.038 Uiso 1 1 calc R C51 C 0.6042(6) 0.4483(6) 0.10269(7) 0.0324(10) Uani 1 1 d . H51 H 0.7121 0.5333 0.0976 0.039 Uiso 1 1 calc R C61 C 0.5077(5) 0.5346(6) 0.06765(7) 0.0325(9) Uani 1 1 d . C71 C 0.5953(6) 0.2799(6) 0.10128(7) 0.0354(10) Uani 1 1 d . C81 C 0.3641(6) 0.5502(6) 0.05828(7) 0.0346(10) Uani 1 1 d . C91 C 0.2051(7) 0.4585(7) 0.06590(8) 0.0439(11) Uani 1 1 d . H91 H 0.1851 0.3957 0.0782 0.053 Uiso 1 1 calc R C101 C 0.0753(8) 0.4589(8) 0.05547(9) 0.0573(15) Uani 1 1 d . H101 H -0.0303 0.3995 0.0610 0.069 Uiso 1 1 calc R C111 C 0.1035(8) 0.5481(8) 0.03680(10) 0.0571(16) Uani 1 1 d . H111 H 0.0166 0.5447 0.0293 0.069 Uiso 1 1 calc R C121 C 0.2574(8) 0.6394(8) 0.02968(10) 0.0575(16) Uani 1 1 d . H121 H 0.2768 0.7028 0.0175 0.069 Uiso 1 1 calc R C131 C 0.3888(7) 0.6420(7) 0.04011(8) 0.0480(13) Uani 1 1 d . H131 H 0.4944 0.7062 0.0348 0.058 Uiso 1 1 calc R C141 C 0.6714(6) 0.6941(6) 0.06614(7) 0.0356(10) Uani 1 1 d . C151 C 0.6856(7) 0.8419(6) 0.07230(8) 0.0455(12) Uani 1 1 d . H151 H 0.5930 0.8454 0.0767 0.055 Uiso 1 1 calc R C161 C 0.8343(8) 0.9823(7) 0.07197(10) 0.0586(15) Uani 1 1 d . H161 H 0.8409 1.0796 0.0765 0.070 Uiso 1 1 calc R C171 C 0.9737(8) 0.9853(9) 0.06529(10) 0.0672(17) Uani 1 1 d . H171 H 1.0737 1.0826 0.0649 0.081 Uiso 1 1 calc R C181 C 0.9607(8) 0.8385(8) 0.05906(10) 0.0627(17) Uani 1 1 d . H181 H 1.0540 0.8365 0.0546 0.075 Uiso 1 1 calc R C191 C 0.8128(6) 0.6960(7) 0.05931(8) 0.0450(12) Uani 1 1 d . H191 H 0.8068 0.5989 0.0548 0.054 Uiso 1 1 calc R C201 C 0.4281(6) 0.1314(6) 0.10593(8) 0.0400(11) Uani 1 1 d . C211 C 0.3138(7) 0.1302(7) 0.11982(9) 0.0476(13) Uani 1 1 d . H211 H 0.3345 0.2278 0.1263 0.057 Uiso 1 1 calc R C221 C 0.1695(7) -0.0121(8) 0.12441(10) 0.0616(16) Uani 1 1 d . H221 H 0.0945 -0.0093 0.1338 0.074 Uiso 1 1 calc R C231 C 0.1364(9) -0.1569(8) 0.11519(13) 0.072(2) Uani 1 1 d . H231 H 0.0399 -0.2530 0.1185 0.086 Uiso 1 1 calc R C241 C 0.2436(10) -0.1596(8) 0.10135(14) 0.081(2) Uani 1 1 d . H241 H 0.2211 -0.2580 0.0950 0.097 Uiso 1 1 calc R C251 C 0.3882(8) -0.0166(8) 0.09640(11) 0.0636(16) Uani 1 1 d . H251 H 0.4597 -0.0204 0.0865 0.076 Uiso 1 1 calc R C261 C 0.7251(6) 0.2827(6) 0.11660(8) 0.0364(11) Uani 1 1 d . C271 C 0.8850(7) 0.3590(8) 0.11038(10) 0.0568(15) Uani 1 1 d . H271 H 0.9140 0.4116 0.0972 0.068 Uiso 1 1 calc R C281 C 1.0059(9) 0.3603(10) 0.12324(11) 0.073(2) Uani 1 1 d . H281 H 1.1132 0.4084 0.1183 0.088 Uiso 1 1 calc R C291 C 0.9684(8) 0.2922(9) 0.14288(11) 0.0621(17) Uani 1 1 d . H291 H 1.0487 0.2938 0.1517 0.074 Uiso 1 1 calc R C301 C 0.8115(9) 0.2219(11) 0.14934(10) 0.082(2) Uani 1 1 d . H301 H 0.7848 0.1764 0.1630 0.098 Uiso 1 1 calc R C311 C 0.6887(8) 0.2145(10) 0.13658(9) 0.0672(19) Uani 1 1 d . H311 H 0.5813 0.1633 0.1415 0.081 Uiso 1 1 calc R C321 C 0.4425(7) 0.5968(8) 0.14338(8) 0.0473(13) Uani 1 1 d . H32A H 0.3639 0.6320 0.1403 0.057 Uiso 1 1 calc R H32B H 0.3843 0.4855 0.1488 0.057 Uiso 1 1 calc R C331 C 0.5696(9) 0.7109(11) 0.15931(10) 0.092(3) Uani 1 1 d . H33C H 0.5431 0.7925 0.1642 0.110 Uiso 1 1 calc R H33D H 0.5728 0.6495 0.1716 0.110 Uiso 1 1 calc R C341 C 0.7304(7) 0.7911(9) 0.14819(9) 0.0655(17) Uani 1 1 d . H34A H 0.7915 0.7364 0.1516 0.079 Uiso 1 1 calc R H34B H 0.7948 0.9053 0.1524 0.079 Uiso 1 1 calc R C351 C 0.6908(6) 0.7767(7) 0.12452(8) 0.0462(12) Uani 1 1 d . H35C H 0.7798 0.7832 0.1160 0.055 Uiso 1 1 calc R H35D H 0.6667 0.8607 0.1199 0.055 Uiso 1 1 calc R Te12 Te 0.20897(5) -0.02323(5) -0.009930(6) 0.05345(11) Uani 1 1 d . N12 N 0.5581(6) 0.0803(7) -0.01117(8) 0.0552(12) Uani 1 1 d . C22 C 0.4435(6) 0.0466(6) 0.00321(8) 0.0410(11) Uani 1 1 d . C32 C 0.4725(7) 0.0600(7) 0.02506(8) 0.0498(13) Uani 1 1 d . H33 H 0.3883 0.0368 0.0347 0.060 Uiso 1 1 calc R C42 C 0.6263(8) 0.1078(8) 0.03213(9) 0.0571(16) Uani 1 1 d . H43 H 0.6488 0.1200 0.0467 0.069 Uiso 1 1 calc R C53 C 0.7463(8) 0.1376(9) 0.01808(9) 0.0682(19) Uani 1 1 d . H53 H 0.8516 0.1679 0.0227 0.082 Uiso 1 1 calc R C62 C 0.7078(9) 0.1218(10) -0.00331(11) 0.074(2) Uani 1 1 d . H63 H 0.7901 0.1408 -0.0131 0.089 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O11 0.0477(19) 0.049(2) 0.0196(15) -0.0012(14) -0.0029(14) 0.0280(17) O21 0.050(2) 0.0417(18) 0.0229(16) -0.0043(14) -0.0008(14) 0.0263(17) O31 0.0414(19) 0.052(2) 0.0324(17) -0.0076(15) -0.0074(14) 0.0322(17) O41 0.057(2) 0.064(2) 0.0240(16) -0.0025(15) -0.0024(15) 0.044(2) C21 0.038(3) 0.049(3) 0.028(2) -0.003(2) -0.0002(19) 0.026(2) C41 0.035(2) 0.035(2) 0.027(2) -0.0023(17) -0.0007(18) 0.0199(19) C51 0.036(2) 0.046(3) 0.020(2) 0.0003(19) 0.0014(18) 0.024(2) C61 0.038(2) 0.037(2) 0.026(2) 0.0000(18) -0.0006(18) 0.0212(19) C71 0.038(2) 0.046(3) 0.028(2) -0.006(2) -0.0051(19) 0.026(2) C81 0.046(3) 0.037(2) 0.025(2) -0.0033(18) -0.0048(19) 0.024(2) C91 0.046(3) 0.054(3) 0.036(2) 0.003(2) -0.003(2) 0.029(3) C101 0.055(4) 0.077(4) 0.048(3) -0.009(3) -0.008(3) 0.040(3) C111 0.063(4) 0.065(4) 0.059(4) -0.010(3) -0.026(3) 0.044(3) C121 0.073(4) 0.057(4) 0.048(3) 0.008(3) -0.019(3) 0.036(3) C131 0.057(3) 0.047(3) 0.040(3) 0.005(2) -0.007(2) 0.026(3) C141 0.042(3) 0.044(3) 0.022(2) 0.0033(19) -0.0024(18) 0.023(2) C151 0.056(3) 0.041(3) 0.043(3) 0.004(2) 0.001(2) 0.027(3) C161 0.070(4) 0.036(3) 0.058(3) -0.007(3) -0.015(3) 0.017(3) C171 0.053(4) 0.057(4) 0.064(4) 0.003(3) -0.007(3) 0.006(3) C181 0.047(3) 0.064(4) 0.066(4) 0.004(3) 0.010(3) 0.020(3) C191 0.043(3) 0.052(3) 0.039(3) 0.000(2) 0.001(2) 0.022(3) C201 0.041(3) 0.043(3) 0.042(3) 0.004(2) -0.002(2) 0.024(2) C211 0.049(3) 0.046(3) 0.045(3) -0.003(2) 0.003(2) 0.022(3) C221 0.050(4) 0.063(4) 0.058(3) 0.007(3) 0.007(3) 0.019(3) C231 0.053(4) 0.049(4) 0.099(6) 0.004(4) -0.007(4) 0.014(3) C241 0.073(5) 0.043(4) 0.123(7) -0.020(4) -0.010(5) 0.025(3) C251 0.070(4) 0.055(4) 0.076(4) -0.007(3) 0.006(3) 0.038(3) C261 0.039(3) 0.045(3) 0.033(2) -0.002(2) -0.0040(19) 0.027(2) C271 0.046(3) 0.078(4) 0.041(3) -0.001(3) 0.000(3) 0.026(3) C281 0.051(4) 0.113(6) 0.059(4) -0.010(4) -0.014(3) 0.043(4) C291 0.054(4) 0.083(5) 0.060(4) -0.008(3) -0.020(3) 0.043(3) C301 0.080(5) 0.136(7) 0.043(3) 0.027(4) -0.009(3) 0.064(5) C311 0.062(4) 0.114(6) 0.038(3) 0.023(4) 0.006(3) 0.053(4) C321 0.044(3) 0.068(4) 0.025(2) -0.007(2) 0.003(2) 0.025(3) C331 0.067(5) 0.118(6) 0.045(4) -0.037(4) 0.003(3) 0.012(4) C341 0.056(4) 0.069(4) 0.052(3) -0.012(3) -0.013(3) 0.016(3) C351 0.043(3) 0.045(3) 0.045(3) -0.003(2) 0.001(2) 0.019(2) Te12 0.0424(2) 0.0545(2) 0.05342(19) -0.00853(19) -0.00840(17) 0.01665(17) N12 0.052(3) 0.067(3) 0.054(3) 0.002(2) -0.002(2) 0.035(3) C22 0.043(3) 0.042(3) 0.036(3) 0.007(2) -0.003(2) 0.019(2) C32 0.060(4) 0.062(4) 0.034(3) 0.001(2) 0.005(3) 0.036(3) C42 0.072(4) 0.081(4) 0.027(3) -0.010(3) -0.012(3) 0.045(4) C53 0.058(4) 0.111(6) 0.042(3) -0.020(3) -0.019(3) 0.047(4) C62 0.057(4) 0.118(6) 0.050(4) -0.015(4) -0.004(3) 0.045(4) 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' 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_3 C51 O11 C21 107.4(3) . C61 O21 H21O 117.8 . C41 O31 C21 109.1(3) . C71 O41 H41O 117.1 . O11 C21 O31 105.1(4) . O11 C21 C351 111.1(4) . O31 C21 C351 114.3(4) . O11 C21 C321 109.6(4) . O31 C21 C321 112.6(4) . C351 C21 C321 104.2(4) . O31 C41 C51 104.4(3) . O31 C41 C61 110.0(4) . C51 C41 C61 117.5(4) . O31 C41 H41 108.2 . C51 C41 H41 108.2 . C61 C41 H41 108.2 . O11 C51 C41 101.6(3) . O11 C51 C71 110.7(4) . C41 C51 C71 117.9(4) . O11 C51 H51 108.8 . C41 C51 H51 108.8 . C71 C51 H51 108.8 . O21 C61 C141 111.0(4) . O21 C61 C81 106.9(3) . C141 C61 C81 112.6(4) . O21 C61 C41 103.1(3) . C141 C61 C41 111.4(4) . C81 C61 C41 111.3(4) . O41 C71 C201 110.3(4) . O41 C71 C261 105.6(4) . C201 C71 C261 110.1(4) . O41 C71 C51 106.7(4) . C201 C71 C51 115.5(4) . C261 C71 C51 108.1(4) . C131 C81 C91 117.8(5) . C131 C81 C61 119.4(4) . C91 C81 C61 122.3(4) . C81 C91 C101 121.0(5) . C81 C91 H91 119.5 . C101 C91 H91 119.5 . C111 C101 C91 119.8(6) . C111 C101 H101 120.1 . C91 C101 H101 120.1 . C121 C111 C101 119.2(5) . C121 C111 H111 120.4 . C101 C111 H111 120.4 . C111 C121 C131 121.7(6) . C111 C121 H121 119.2 . C131 C121 H121 119.2 . C81 C131 C121 120.5(6) . C81 C131 H131 119.8 . C121 C131 H131 119.8 . C151 C141 C191 117.5(5) . C151 C141 C61 121.0(4) . C191 C141 C61 121.4(5) . C161 C151 C141 120.5(5) . C161 C151 H151 119.8 . C141 C151 H151 119.8 . C151 C161 C171 122.4(6) . C151 C161 H161 118.8 . C171 C161 H161 118.8 . C161 C171 C181 117.6(6) . C161 C171 H171 121.2 . C181 C171 H171 121.2 . C191 C181 C171 121.0(6) . C191 C181 H181 119.5 . C171 C181 H181 119.5 . C181 C191 C141 121.0(6) . C181 C191 H191 119.5 . C141 C191 H191 119.5 . C211 C201 C251 116.5(5) . C211 C201 C71 124.9(5) . C251 C201 C71 118.6(5) . C201 C211 C221 121.6(5) . C201 C211 H211 119.2 . C221 C211 H211 119.2 . C231 C221 C211 120.3(6) . C231 C221 H221 119.8 . C211 C221 H221 119.8 . C241 C231 C221 119.6(6) . C241 C231 H231 120.2 . C221 C231 H231 120.2 . C231 C241 C251 120.6(6) . C231 C241 H241 119.7 . C251 C241 H241 119.7 . C201 C251 C241 121.4(6) . C201 C251 H251 119.3 . C241 C251 H251 119.3 . C271 C261 C311 117.4(5) . C271 C261 C71 119.3(5) . C311 C261 C71 123.3(5) . C261 C271 C281 121.7(6) . C261 C271 H271 119.2 . C281 C271 H271 119.2 . C291 C281 C271 120.3(7) . C291 C281 H281 119.9 . C271 C281 H281 119.9 . C301 C291 C281 118.0(6) . C301 C291 H291 121.0 . C281 C291 H291 121.0 . C291 C301 C311 122.6(6) . C291 C301 H301 118.7 . C311 C301 H301 118.7 . C261 C311 C301 119.9(6) . C261 C311 H311 120.1 . C301 C311 H311 120.1 . C331 C321 C21 104.9(5) . C331 C321 H32A 110.8 . C21 C321 H32A 110.8 . C331 C321 H32B 110.8 . C21 C321 H32B 110.8 . H32A C321 H32B 108.8 . C341 C331 C321 107.3(5) . C341 C331 H33C 110.3 . C321 C331 H33C 110.3 . C341 C331 H33D 110.3 . C321 C331 H33D 110.3 . H33C C331 H33D 108.5 . C331 C341 C351 105.6(5) . C331 C341 H34A 110.6 . C351 C341 H34A 110.6 . C331 C341 H34B 110.6 . C351 C341 H34B 110.6 . H34A C341 H34B 108.7 . C341 C351 C21 101.5(4) . C341 C351 H35C 111.5 . C21 C351 H35C 111.5 . C341 C351 H35D 111.5 . C21 C351 H35D 111.5 . H35C C351 H35D 109.3 . C22 Te12 Te12 90.55(14) 5 C22 N12 C62 115.6(5) . N12 C22 C32 123.4(5) . N12 C22 Te12 114.2(4) . C32 C22 Te12 122.3(4) . C42 C32 C22 118.6(5) . C42 C32 H33 120.7 . C22 C32 H33 120.7 . C53 C42 C32 120.1(5) . C53 C42 H43 119.9 . C32 C42 H43 119.9 . C42 C53 C62 117.6(6) . C42 C53 H53 121.2 . C62 C53 H53 121.2 . N12 C62 C53 124.4(6) . N12 C62 H63 117.8 . C53 C62 H63 117.8 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O11 C51 1.413(5) . O11 C21 1.413(6) . O21 C61 1.425(5) . O21 H21O 0.8584 . O31 C41 1.417(5) . O31 C21 1.431(5) . O41 C71 1.421(5) . O41 H41O 0.8600 . C21 C351 1.519(7) . C21 C321 1.523(6) . C41 C51 1.545(6) . C41 C61 1.556(6) . C41 H41 0.9800 . C51 C71 1.548(7) . C51 H51 0.9800 . C61 C141 1.525(6) . C61 C81 1.547(6) . C71 C201 1.523(7) . C71 C261 1.543(6) . C81 C131 1.375(7) . C81 C91 1.386(7) . C91 C101 1.387(8) . C91 H91 0.9300 . C101 C111 1.384(9) . C101 H101 0.9300 . C111 C121 1.339(9) . C111 H111 0.9300 . C121 C131 1.388(8) . C121 H121 0.9300 . C131 H131 0.9300 . C141 C151 1.385(7) . C141 C191 1.390(7) . C151 C161 1.363(8) . C151 H151 0.9300 . C161 C171 1.364(9) . C161 H161 0.9300 . C171 C181 1.382(10) . C171 H171 0.9300 . C181 C191 1.368(8) . C181 H181 0.9300 . C191 H191 0.9300 . C201 C211 1.379(7) . C201 C251 1.384(8) . C211 C221 1.380(8) . C211 H211 0.9300 . C221 C231 1.365(9) . C221 H221 0.9300 . C231 C241 1.339(10) . C231 H231 0.9300 . C241 C251 1.389(10) . C241 H241 0.9300 . C251 H251 0.9300 . C261 C271 1.361(7) . C261 C311 1.367(7) . C271 C281 1.389(9) . C271 H271 0.9300 . C281 C291 1.348(9) . C281 H281 0.9300 . C291 C301 1.344(9) . C291 H291 0.9300 . C301 C311 1.378(8) . C301 H301 0.9300 . C311 H311 0.9300 . C321 C331 1.514(8) . C321 H32A 0.9700 . C321 H32B 0.9700 . C331 C341 1.484(9) . C331 H33C 0.9700 . C331 H33D 0.9700 . C341 C351 1.514(7) . C341 H34A 0.9700 . C341 H34B 0.9700 . C351 H35C 0.9700 . C351 H35D 0.9700 . Te12 C22 2.129(5) . Te12 Te12 2.7072(8) 5 N12 C22 1.315(7) . N12 C62 1.353(8) . C22 C32 1.386(7) . C32 C42 1.359(8) . C32 H33 0.9300 . C42 C53 1.346(9) . C42 H43 0.9300 . C53 C62 1.374(8) . C53 H53 0.9300 . C62 H63 0.9300 . 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 O21 H21O N12 0.86 2.03 2.873(6) 169.2 5 O41 H41O O21 0.86 1.88 2.694(5) 158.4 . 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 C51 O11 C21 O31 33.0(5) . C51 O11 C21 C351 -91.1(4) . C51 O11 C21 C321 154.3(4) . C41 O31 C21 O11 -15.7(5) . C41 O31 C21 C351 106.4(4) . C41 O31 C21 C321 -135.0(4) . C21 O31 C41 C51 -5.7(5) . C21 O31 C41 C61 -132.6(4) . C21 O11 C51 C41 -35.4(5) . C21 O11 C51 C71 -161.4(4) . O31 C41 C51 O11 24.7(4) . C61 C41 C51 O11 146.9(4) . O31 C41 C51 C71 145.8(4) . C61 C41 C51 C71 -92.1(5) . O31 C41 C61 O21 -174.2(3) . C51 C41 C61 O21 66.6(5) . O31 C41 C61 C141 66.7(5) . C51 C41 C61 C141 -52.6(5) . O31 C41 C61 C81 -59.9(5) . C51 C41 C61 C81 -179.2(4) . O11 C51 C71 O41 -169.2(4) . C41 C51 C71 O41 74.6(5) . O11 C51 C71 C201 67.8(5) . C41 C51 C71 C201 -48.4(6) . O11 C51 C71 C261 -56.0(5) . C41 C51 C71 C261 -172.3(4) . O21 C61 C81 C131 -83.6(5) . C141 C61 C81 C131 38.5(6) . C41 C61 C81 C131 164.5(4) . O21 C61 C81 C91 88.0(5) . C141 C61 C81 C91 -149.8(5) . C41 C61 C81 C91 -23.9(6) . C131 C81 C91 C101 0.2(8) . C61 C81 C91 C101 -171.5(5) . C81 C91 C101 C111 2.0(8) . C91 C101 C111 C121 -3.3(9) . C101 C111 C121 C131 2.5(10) . C91 C81 C131 C121 -1.1(8) . C61 C81 C131 C121 170.9(5) . C111 C121 C131 C81 -0.3(9) . O21 C61 C141 C151 166.9(4) . C81 C61 C141 C151 47.1(6) . C41 C61 C141 C151 -78.8(5) . O21 C61 C141 C191 -15.5(6) . C81 C61 C141 C191 -135.3(5) . C41 C61 C141 C191 98.8(5) . C191 C141 C151 C161 -1.2(8) . C61 C141 C151 C161 176.5(5) . C141 C151 C161 C171 1.3(9) . C151 C161 C171 C181 -1.1(10) . C161 C171 C181 C191 0.9(10) . C171 C181 C191 C141 -1.0(9) . C151 C141 C191 C181 1.1(8) . C61 C141 C191 C181 -176.6(5) . O41 C71 C201 C211 -152.3(5) . C261 C71 C201 C211 91.6(6) . C51 C71 C201 C211 -31.2(7) . O41 C71 C201 C251 30.7(6) . C261 C71 C201 C251 -85.4(6) . C51 C71 C201 C251 151.8(5) . C251 C201 C211 C221 1.8(8) . C71 C201 C211 C221 -175.2(5) . C201 C211 C221 C231 0.1(10) . C211 C221 C231 C241 -1.1(11) . C221 C231 C241 C251 0.2(12) . C211 C201 C251 C241 -2.7(9) . C71 C201 C251 C241 174.5(6) . C231 C241 C251 C201 1.8(12) . O41 C71 C261 C271 34.7(6) . C201 C71 C261 C271 153.7(5) . C51 C71 C261 C271 -79.2(6) . O41 C71 C261 C311 -146.6(6) . C201 C71 C261 C311 -27.6(7) . C51 C71 C261 C311 99.5(6) . C311 C261 C271 C281 3.5(10) . C71 C261 C271 C281 -177.8(6) . C261 C271 C281 C291 -3.4(11) . C271 C281 C291 C301 0.9(12) . C281 C291 C301 C311 1.2(13) . C271 C261 C311 C301 -1.4(11) . C71 C261 C311 C301 179.9(7) . C291 C301 C311 C261 -1.0(13) . O11 C21 C321 C331 91.7(6) . O31 C21 C321 C331 -151.7(6) . C351 C21 C321 C331 -27.3(6) . C21 C321 C331 C341 3.8(8) . C321 C331 C341 C351 21.2(9) . C331 C341 C351 C21 -37.6(7) . O11 C21 C351 C341 -78.3(5) . O31 C21 C351 C341 163.0(4) . C321 C21 C351 C341 39.7(5) . C62 N12 C22 C32 3.3(9) . C62 N12 C22 Te12 -178.7(5) . Te12 Te12 C22 N12 -120.3(4) 5 Te12 Te12 C22 C32 57.8(5) 5 N12 C22 C32 C42 -1.1(9) . Te12 C22 C32 C42 -179.0(4) . C22 C32 C42 C53 -1.5(10) . C32 C42 C53 C62 1.6(11) . C22 N12 C62 C53 -3.2(11) . C42 C53 C62 N12 0.9(12) . _journal_paper_doi 10.1021/ol300870s