# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Prof Rolf Gleiter' _publ_contact_author_address ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 D-69120 Heidelberg Germany ; _publ_contact_author_phone '049 6221 54- 8400' _publ_contact_author_fax '049 6221 54- 4205' _publ_contact_author_email rolf.gleiter@urz.uni-heidelberg.de _publ_requested_coeditor_name ? _publ_contact_letter ; paper to be submitted for publication in Organic and Biomolecular Chemistry ; #======================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Syntheses and Solid State Structures of Cyclic Diynes with Two Chalcogen Centers A Competition Between Weak Interactions ; loop_ _publ_author_name _publ_author_address H.J.Schulte ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; D.B.Werz ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; F.Rominger ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; R.Gleiter ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; #===END data_hse22_(in_paper_4S23) _database_code_CSD 207497 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 S2' _chemical_formula_weight 210.34 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.5954(2) _cell_length_b 9.59610(10) _cell_length_c 9.1230(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.3180(10) _cell_angle_gamma 90.00 _cell_volume 1129.90(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.425 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8418 _exptl_absorpt_correction_T_max 0.9628 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11416 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2592 _reflns_number_gt 2062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.6157P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2592 _refine_ls_number_parameters 150 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.003 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 C2 C 0.85365(16) 0.7671(2) 0.0914(2) 0.0460(5) Uani 1 1 d D A . C3 C 0.79796(16) 0.8508(2) 0.1206(2) 0.0454(5) Uani 1 1 d D . . C4 C 0.72905(18) 0.9465(2) 0.1653(3) 0.0543(5) Uani 1 1 d . . . H4A H 0.6916 1.0046 0.0754 0.065 Uiso 1 1 calc R . . H4B H 0.7706 1.0092 0.2477 0.065 Uiso 1 1 calc R . . C5 C 0.65066(16) 0.8676(2) 0.2232(2) 0.0474(5) Uani 1 1 d . . . H5A H 0.6879 0.7980 0.3010 0.057 Uiso 1 1 calc R . . H5B H 0.6166 0.9341 0.2747 0.057 Uiso 1 1 calc R . . C6 C 0.56797(16) 0.7935(2) 0.0940(2) 0.0489(5) Uani 1 1 d . . . H6A H 0.5157 0.8626 0.0375 0.059 Uiso 1 1 calc R . . H6B H 0.6006 0.7539 0.0204 0.059 Uiso 1 1 calc R . . C7 C 0.51349(15) 0.6771(2) 0.1520(2) 0.0494(5) Uani 1 1 d . . . H7A H 0.4913 0.7121 0.2388 0.059 Uiso 1 1 calc R . . H7B H 0.4507 0.6482 0.0681 0.059 Uiso 1 1 calc R . . C8 C 0.58145(15) 0.5564(2) 0.2037(2) 0.0475(5) Uani 1 1 d D A . C9 C 0.63919(16) 0.4606(2) 0.2377(3) 0.0519(5) Uani 1 1 d DU . . S2 S 0.7224(2) 0.3233(3) 0.2835(4) 0.0885(10) Uani 0.706(6) 1 d PDU A 1 C11 C 0.8209(3) 0.3831(4) 0.1958(4) 0.0528(10) Uani 0.706(6) 1 d PDU A 1 H11A H 0.8665 0.3044 0.1892 0.063 Uiso 0.706(6) 1 calc PR A 1 H11B H 0.7864 0.4182 0.0900 0.063 Uiso 0.706(6) 1 calc PR A 1 C12 C 0.8854(2) 0.4994(3) 0.2960(3) 0.0436(8) Uani 0.706(6) 1 d PDU A 1 H12A H 0.8387 0.5771 0.3012 0.052 Uiso 0.706(6) 1 calc PR A 1 H12B H 0.9172 0.4636 0.4022 0.052 Uiso 0.706(6) 1 calc PR A 1 C13 C 0.9700(3) 0.5547(5) 0.2370(5) 0.0477(9) Uani 0.706(6) 1 d PDU A 1 H13A H 1.0141 0.4751 0.2284 0.057 Uiso 0.706(6) 1 calc PR A 1 H13B H 1.0137 0.6183 0.3164 0.057 Uiso 0.706(6) 1 calc PR A 1 S1 S 0.93282(5) 0.64554(7) 0.05609(7) 0.0609(2) Uani 1 1 d DU . . S2B S 0.7110(4) 0.3166(6) 0.2736(7) 0.0587(15) Uani 0.294(6) 1 d PDU A 2 C11B C 0.8385(6) 0.3886(9) 0.3293(11) 0.065(3) Uani 0.294(6) 1 d PDU A 2 H11C H 0.8484 0.4569 0.4140 0.078 Uiso 0.294(6) 1 calc PR A 2 H11D H 0.8917 0.3147 0.3627 0.078 Uiso 0.294(6) 1 calc PR A 2 C12B C 0.8433(7) 0.4592(11) 0.1819(13) 0.070(3) Uani 0.294(6) 1 d PDU A 2 H12C H 0.8334 0.3893 0.0987 0.085 Uiso 0.294(6) 1 calc PR A 2 H12D H 0.7875 0.5296 0.1477 0.085 Uiso 0.294(6) 1 calc PR A 2 C13B C 0.9445(9) 0.5263(14) 0.2136(15) 0.067(5) Uiso 0.294(6) 1 d PDU A 2 H13C H 0.9988 0.4559 0.2190 0.081 Uiso 0.294(6) 1 calc PR A 2 H13D H 0.9630 0.5772 0.3130 0.081 Uiso 0.294(6) 1 calc PR A 2 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 C2 0.0482(11) 0.0450(11) 0.0443(11) 0.0004(9) 0.0138(9) -0.0058(9) C3 0.0500(11) 0.0394(10) 0.0447(11) 0.0045(8) 0.0117(9) -0.0069(9) C4 0.0650(14) 0.0331(10) 0.0624(13) 0.0037(9) 0.0165(11) 0.0058(9) C5 0.0510(11) 0.0446(11) 0.0453(10) -0.0021(9) 0.0135(9) 0.0107(9) C6 0.0464(11) 0.0562(12) 0.0403(10) 0.0043(9) 0.0083(8) 0.0139(9) C7 0.0363(10) 0.0593(13) 0.0496(11) -0.0060(9) 0.0092(8) 0.0067(9) C8 0.0396(10) 0.0487(11) 0.0547(12) -0.0081(9) 0.0157(9) -0.0042(9) C9 0.0461(11) 0.0414(11) 0.0699(14) -0.0063(10) 0.0206(10) -0.0038(9) S2 0.0834(16) 0.0385(10) 0.161(3) 0.0222(12) 0.0632(15) 0.0124(9) C11 0.0485(18) 0.048(2) 0.063(2) -0.0060(17) 0.0202(16) 0.0103(16) C12 0.0427(15) 0.0470(16) 0.0372(16) 0.0008(12) 0.0068(12) 0.0044(12) C13 0.0365(18) 0.053(2) 0.0505(19) -0.0016(16) 0.0091(15) 0.0058(17) S1 0.0671(4) 0.0677(4) 0.0576(4) 0.0008(3) 0.0335(3) 0.0099(3) S2B 0.0330(15) 0.0307(19) 0.095(3) -0.0201(18) -0.0053(16) -0.0017(12) C11B 0.060(4) 0.057(5) 0.078(7) 0.007(4) 0.020(4) 0.018(4) C12B 0.058(6) 0.061(6) 0.097(9) 0.025(6) 0.031(6) 0.020(5) _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 C2 C3 1.190(3) . ? C2 S1 1.685(2) . ? C3 C4 1.458(3) . ? C4 C5 1.530(3) . ? C5 C6 1.525(3) . ? C6 C7 1.524(3) . ? C7 C8 1.464(3) . ? C8 C9 1.185(3) . ? C9 S2B 1.664(6) . ? C9 S2 1.701(3) . ? S2 C11 1.854(5) . ? C11 C12 1.531(5) . ? C12 C13 1.512(5) . ? C13 S1 1.793(4) . ? S1 C13B 1.804(11) . ? S2B C11B 1.785(9) . ? C11B C12B 1.525(11) . ? C12B C13B 1.464(12) . ? 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 C3 C2 S1 177.97(19) . . ? C2 C3 C4 175.7(2) . . ? C3 C4 C5 111.31(17) . . ? C6 C5 C4 112.82(18) . . ? C7 C6 C5 113.21(17) . . ? C8 C7 C6 111.43(17) . . ? C9 C8 C7 175.5(2) . . ? C8 C9 S2B 174.3(2) . . ? C8 C9 S2 179.0(3) . . ? S2B C9 S2 5.5(2) . . ? C9 S2 C11 99.74(19) . . ? C12 C11 S2 108.9(2) . . ? C13 C12 C11 113.6(3) . . ? C12 C13 S1 118.2(3) . . ? C2 S1 C13 99.92(15) . . ? C2 S1 C13B 100.8(5) . . ? C13 S1 C13B 14.0(4) . . ? C9 S2B C11B 101.1(4) . . ? C12B C11B S2B 103.1(7) . . ? C13B C12B C11B 108.6(9) . . ? C12B C13B S1 106.2(8) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.603 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.042 #===END data_hse15_(in_paper_5S22) _database_code_CSD 207498 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 S2' _chemical_formula_weight 210.34 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I-4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 20.0210(17) _cell_length_b 20.0210(17) _cell_length_c 5.6850(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2278.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max .44 _exptl_crystal_size_mid .16 _exptl_crystal_size_min .13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.421 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3482 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2261 _reflns_number_gt 1655 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.5764P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(12) _refine_ls_number_reflns 2261 _refine_ls_number_parameters 155 _refine_ls_number_restraints 50 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.00374(3) 0.40508(3) -0.98112(15) 0.0464(2) Uani 1 1 d . . . S2 S 0.06410(4) 0.25998(4) -1.51874(17) 0.0597(3) Uani 1 1 d . . . C1 C 0.04721(14) 0.34368(15) -1.1362(5) 0.0440(7) Uani 1 1 d . . . H1A H 0.0931 0.3613 -1.1550 0.053 Uiso 1 1 calc R . . H1B H 0.0498 0.3023 -1.0414 0.053 Uiso 1 1 calc R . . C2 C 0.01897(15) 0.32756(14) -1.3733(5) 0.0476(7) Uani 1 1 d . . . H2A H 0.0208 0.3680 -1.4734 0.057 Uiso 1 1 calc R . . H2B H -0.0285 0.3146 -1.3557 0.057 Uiso 1 1 calc R . . C4 C 0.02185(17) 0.19426(17) -1.4046(6) 0.0554(9) Uani 1 1 d D . . C5 C -0.00971(19) 0.14934(18) -1.3248(7) 0.0655(10) Uani 1 1 d D A . C6 C -0.0537(2) 0.09846(18) -1.2232(9) 0.0855(13) Uani 1 1 d DU . . H6A H -0.0302 0.0761 -1.0917 0.103 Uiso 0.734(8) 1 calc PR A 1 H6B H -0.0636 0.0643 -1.3440 0.103 Uiso 0.734(8) 1 calc PR A 1 H6C H -0.0270 0.0584 -1.1838 0.103 Uiso 0.266(8) 1 calc PR A 2 H6D H -0.0875 0.0853 -1.3416 0.103 Uiso 0.266(8) 1 calc PR A 2 C7 C -0.1179(3) 0.1272(3) -1.1346(12) 0.0693(19) Uani 0.734(8) 1 d PDU A 1 H7A H -0.1472 0.0905 -1.0804 0.083 Uiso 0.734(8) 1 calc PR A 1 H7B H -0.1409 0.1505 -1.2649 0.083 Uiso 0.734(8) 1 calc PR A 1 C8 C -0.1067(5) 0.1756(5) -0.9344(13) 0.076(2) Uani 0.734(8) 1 d PDU A 1 H8A H -0.0692 0.2059 -0.9735 0.091 Uiso 0.734(8) 1 calc PR A 1 H8B H -0.0947 0.1506 -0.7901 0.091 Uiso 0.734(8) 1 calc PR A 1 C9 C -0.1718(3) 0.2175(3) -0.8895(14) 0.082(2) Uani 0.734(8) 1 d PDU A 1 H9A H -0.1878 0.2364 -1.0403 0.099 Uiso 0.734(8) 1 calc PR A 1 H9B H -0.2072 0.1879 -0.8271 0.099 Uiso 0.734(8) 1 calc PR A 1 C10 C -0.1596(4) 0.2732(3) -0.7183(12) 0.077(2) Uani 0.734(8) 1 d PDU A 1 H10A H -0.2020 0.2966 -0.6829 0.092 Uiso 0.734(8) 1 calc PR A 1 H10B H -0.1413 0.2551 -0.5695 0.092 Uiso 0.734(8) 1 calc PR A 1 C11 C -0.11088(18) 0.32066(17) -0.8262(7) 0.0708(11) Uani 1 1 d DU . . C12 C -0.06769(15) 0.35525(15) -0.8961(5) 0.0484(8) Uani 1 1 d D A . C7B C -0.0881(15) 0.1223(10) -1.009(5) 0.194(17) Uani 0.266(8) 1 d PDU A 2 H7B1 H -0.0539 0.1307 -0.8867 0.233 Uiso 0.266(8) 1 calc PR A 2 H7B2 H -0.1173 0.0860 -0.9512 0.233 Uiso 0.266(8) 1 calc PR A 2 C8B C -0.1293(16) 0.1836(13) -1.034(4) 0.135(12) Uani 0.266(8) 1 d PDU A 2 H8B1 H -0.1704 0.1745 -1.1258 0.163 Uiso 0.266(8) 1 calc PR A 2 H8B2 H -0.1038 0.2197 -1.1131 0.163 Uiso 0.266(8) 1 calc PR A 2 C9B C -0.1464(7) 0.2030(6) -0.773(3) 0.066(5) Uani 0.266(8) 1 d PDU A 2 H9B1 H -0.1819 0.1746 -0.7038 0.079 Uiso 0.266(8) 1 calc PR A 2 H9B2 H -0.1067 0.2033 -0.6689 0.079 Uiso 0.266(8) 1 calc PR A 2 C10B C -0.1711(7) 0.2740(7) -0.836(4) 0.080(7) Uani 0.266(8) 1 d PDU A 2 H10C H -0.1908 0.2742 -0.9957 0.095 Uiso 0.266(8) 1 calc PR A 2 H10D H -0.2056 0.2888 -0.7226 0.095 Uiso 0.266(8) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0477(4) 0.0421(4) 0.0496(4) -0.0015(4) 0.0010(4) -0.0063(3) S2 0.0689(5) 0.0603(5) 0.0498(5) -0.0018(5) 0.0104(5) 0.0107(4) C1 0.0400(15) 0.0504(17) 0.0417(16) 0.0044(15) -0.0041(14) -0.0017(14) C2 0.0506(17) 0.0454(17) 0.0468(17) 0.0063(15) -0.0029(15) 0.0047(15) C4 0.063(2) 0.0512(19) 0.052(2) -0.0101(17) -0.0148(17) 0.0130(17) C5 0.074(2) 0.0454(19) 0.077(3) -0.0047(19) -0.017(2) 0.004(2) C6 0.098(3) 0.052(2) 0.107(3) 0.000(2) -0.032(3) -0.017(2) C7 0.071(4) 0.057(4) 0.080(4) 0.016(3) -0.025(3) -0.020(3) C8 0.072(4) 0.071(4) 0.086(5) 0.004(4) 0.000(4) -0.027(3) C9 0.065(4) 0.088(5) 0.094(5) 0.013(4) 0.007(4) -0.035(3) C10 0.072(4) 0.086(5) 0.073(5) 0.022(3) 0.012(4) -0.013(3) C11 0.053(2) 0.054(2) 0.105(3) 0.011(2) 0.020(2) -0.0017(18) C12 0.0503(18) 0.0444(17) 0.0505(19) 0.0031(15) 0.0032(15) 0.0052(16) C7B 0.24(3) 0.100(15) 0.25(4) 0.046(19) 0.18(3) -0.032(18) C8B 0.14(3) 0.093(16) 0.17(2) -0.036(19) 0.07(2) -0.070(12) C9B 0.033(8) 0.067(8) 0.097(11) 0.052(8) -0.016(7) -0.011(6) C10B 0.049(9) 0.063(9) 0.127(19) 0.062(10) 0.022(11) 0.000(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C12 1.694(3) . ? S1 C1 1.825(3) . ? S2 C4 1.694(4) . ? S2 C2 1.825(3) . ? C1 C2 1.497(4) . ? C4 C5 1.189(5) . ? C5 C6 1.465(5) . ? C6 C7B 1.478(15) . ? C6 C7 1.495(7) . ? C7 C8 1.511(8) . ? C8 C9 1.573(9) . ? C9 C10 1.500(8) . ? C10 C11 1.493(7) . ? C11 C12 1.177(4) . ? C11 C10B 1.526(13) . ? C7B C8B 1.486(17) . ? C8B C9B 1.577(16) . ? C9B C10B 1.548(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 S1 C1 99.42(14) . . ? C4 S2 C2 98.92(15) . . ? C2 C1 S1 111.7(2) . . ? C1 C2 S2 112.4(2) . . ? C5 C4 S2 177.8(3) . . ? C4 C5 C6 174.6(4) . . ? C5 C6 C7B 112.3(9) . . ? C5 C6 C7 112.5(4) . . ? C7B C6 C7 36.6(14) . . ? C6 C7 C8 111.9(5) . . ? C7 C8 C9 110.0(6) . . ? C10 C9 C8 111.5(6) . . ? C11 C10 C9 108.3(5) . . ? C12 C11 C10 173.1(5) . . ? C12 C11 C10B 158.2(10) . . ? C10 C11 C10B 27.1(8) . . ? C11 C12 S1 176.8(3) . . ? C6 C7B C8B 116.5(18) . . ? C7B C8B C9B 103.4(16) . . ? C10B C9B C8B 94.3(13) . . ? C11 C10B C9B 107.5(11) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.218 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.037 #===END data_hse13_(in_paper_5S23) _database_code_CSD 207499 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 S2' _chemical_formula_weight 224.37 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 4.54020(10) _cell_length_b 13.4819(2) _cell_length_c 9.7130(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.2740(10) _cell_angle_gamma 90.00 _cell_volume 590.98(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.410 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6006 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2671 _reflns_number_gt 2579 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+0.0529P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(11) _refine_ls_number_reflns 2671 _refine_ls_number_parameters 128 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0630 _refine_ls_wR_factor_gt 0.0620 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.64860(7) 0.80367(3) 0.54770(4) 0.03212(10) Uani 1 1 d . . . S2 S 0.55227(9) 0.49176(2) 0.16772(4) 0.03592(11) Uani 1 1 d . . . C2 C 0.4826(3) 0.87472(11) 0.41846(15) 0.0260(3) Uani 1 1 d . . . C3 C 0.3595(3) 0.92575(11) 0.32926(15) 0.0276(3) Uani 1 1 d . . . C4 C 0.2075(4) 0.98692(12) 0.21712(17) 0.0345(4) Uani 1 1 d . . . H4A H 0.3575 1.0209 0.1673 0.041 Uiso 1 1 calc R . . H4B H 0.0881 1.0384 0.2579 0.041 Uiso 1 1 calc R . . C5 C 0.0029(4) 0.92414(11) 0.11294(16) 0.0316(3) Uani 1 1 d . . . H5A H -0.1475 0.8907 0.1632 0.038 Uiso 1 1 calc R . . H5B H -0.1030 0.9690 0.0435 0.038 Uiso 1 1 calc R . . C6 C 0.1680(3) 0.84622(10) 0.03807(15) 0.0247(3) Uani 1 1 d . . . H6A H 0.3119 0.8798 -0.0158 0.030 Uiso 1 1 calc R . . H6B H 0.2811 0.8032 0.1076 0.030 Uiso 1 1 calc R . . C7 C -0.0361(3) 0.78192(11) -0.05924(15) 0.0276(3) Uani 1 1 d . . . H7A H -0.1465 0.8250 -0.1296 0.033 Uiso 1 1 calc R . . H7B H -0.1825 0.7495 -0.0056 0.033 Uiso 1 1 calc R . . C8 C 0.1288(4) 0.70098(11) -0.13417(15) 0.0292(3) Uani 1 1 d . . . H8A H -0.0149 0.6647 -0.1998 0.035 Uiso 1 1 calc R . . H8B H 0.2759 0.7328 -0.1881 0.035 Uiso 1 1 calc R . . C9 C 0.2812(3) 0.63028(11) -0.03445(15) 0.0284(3) Uani 1 1 d . . . C10 C 0.4003(3) 0.57432(11) 0.04997(15) 0.0273(3) Uani 1 1 d . . . C12 C 0.7927(3) 0.57166(12) 0.28159(16) 0.0309(3) Uani 1 1 d . . . H12A H 0.9061 0.5303 0.3531 0.037 Uiso 1 1 calc R . . H12B H 0.9367 0.6044 0.2268 0.037 Uiso 1 1 calc R . . C13 C 0.6256(3) 0.65060(11) 0.35254(15) 0.0229(3) Uani 1 1 d . . . H13A H 0.4785 0.6186 0.4062 0.027 Uiso 1 1 calc R . . H13B H 0.5174 0.6939 0.2818 0.027 Uiso 1 1 calc R . . C14 C 0.8378(3) 0.71317(11) 0.44926(16) 0.0269(3) Uani 1 1 d . . . H14A H 0.9755 0.7485 0.3939 0.032 Uiso 1 1 calc R . . H14B H 0.9572 0.6687 0.5146 0.032 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 S1 0.0451(2) 0.02915(19) 0.02051(16) -0.00303(14) -0.00348(13) 0.00200(15) S2 0.0533(2) 0.02263(17) 0.02978(18) -0.00383(16) -0.00442(16) 0.00795(18) C2 0.0318(8) 0.0228(7) 0.0234(6) -0.0049(5) 0.0025(6) -0.0018(5) C3 0.0343(8) 0.0238(6) 0.0251(7) -0.0053(5) 0.0050(6) 0.0001(6) C4 0.0489(10) 0.0270(7) 0.0267(7) 0.0017(6) 0.0001(7) 0.0130(7) C5 0.0324(7) 0.0326(8) 0.0288(7) 0.0027(6) -0.0007(6) 0.0105(6) C6 0.0240(7) 0.0252(6) 0.0240(7) 0.0010(5) -0.0009(5) 0.0015(5) C7 0.0254(7) 0.0279(7) 0.0275(7) 0.0055(6) -0.0060(6) -0.0029(6) C8 0.0394(9) 0.0253(7) 0.0206(7) 0.0003(5) -0.0067(6) -0.0058(6) C9 0.0353(8) 0.0252(7) 0.0238(7) -0.0066(5) -0.0004(6) -0.0070(6) C10 0.0353(8) 0.0249(7) 0.0215(6) -0.0054(5) 0.0020(6) -0.0011(6) C12 0.0312(8) 0.0312(8) 0.0288(7) -0.0036(6) -0.0032(6) 0.0094(6) C13 0.0246(7) 0.0225(6) 0.0207(6) -0.0001(5) -0.0015(5) 0.0017(5) C14 0.0266(7) 0.0272(7) 0.0261(7) 0.0002(5) -0.0014(6) 0.0013(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.6896(15) . ? S1 C14 1.8221(15) . ? S2 C10 1.6884(15) . ? S2 C12 1.8199(16) . ? C2 C3 1.196(2) . ? C3 C4 1.476(2) . ? C4 C5 1.549(2) . ? C5 C6 1.521(2) . ? C6 C7 1.5206(19) . ? C7 C8 1.549(2) . ? C8 C9 1.476(2) . ? C9 C10 1.199(2) . ? C12 C13 1.516(2) . ? C13 C14 1.525(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 S1 C14 100.80(7) . . ? C10 S2 C12 101.25(7) . . ? C3 C2 S1 178.24(13) . . ? C2 C3 C4 178.78(15) . . ? C3 C4 C5 112.06(12) . . ? C6 C5 C4 113.45(13) . . ? C7 C6 C5 113.09(12) . . ? C6 C7 C8 113.61(12) . . ? C9 C8 C7 111.25(12) . . ? C10 C9 C8 177.82(15) . . ? C9 C10 S2 177.02(14) . . ? C13 C12 S2 113.27(10) . . ? C12 C13 C14 110.77(12) . . ? C13 C14 S1 113.04(10) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.201 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.034 #===END data_hse21_(in_paper_5S24) _database_code_CSD 207500 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H18 S2' _chemical_formula_weight 238.39 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.2162(2) _cell_length_b 9.07480(10) _cell_length_c 16.3181(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.1770(10) _cell_angle_gamma 90.00 _cell_volume 2626.49(5) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8836 _exptl_absorpt_correction_T_max 0.9393 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20189 _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 24.08 _reflns_number_total 4164 _reflns_number_gt 3200 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.7657P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4164 _refine_ls_number_parameters 290 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.004 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1_1 S 0.17298(4) 1.14989(7) -0.19402(4) 0.03991(19) Uani 1 1 d . A . S2_1 S 0.26299(4) 1.13321(7) 0.16763(4) 0.0401(2) Uani 1 1 d . A . C2_1 C 0.10276(14) 1.0440(3) -0.17376(15) 0.0355(6) Uani 1 1 d . . . C3_1 C 0.05689(15) 0.9547(3) -0.16561(16) 0.0411(6) Uani 1 1 d . . . C4_1 C 0.00149(15) 0.8420(3) -0.15560(19) 0.0506(7) Uani 1 1 d . . . H4A_1 H -0.0147 0.7877 -0.2093 0.061 Uiso 1 1 calc R . . H4B_1 H -0.0434 0.8918 -0.1441 0.061 Uiso 1 1 calc R . . C5_1 C 0.03073(15) 0.7314(3) -0.08540(18) 0.0481(7) Uani 1 1 d . . . H5A_1 H -0.0083 0.6554 -0.0859 0.058 Uiso 1 1 calc R . . H5B_1 H 0.0758 0.6815 -0.0965 0.058 Uiso 1 1 calc R . . C6_1 C 0.05122(15) 0.8021(3) 0.00111(17) 0.0435(7) Uani 1 1 d . . . H6A_1 H 0.0883 0.8816 0.0005 0.052 Uiso 1 1 calc R . . H6B_1 H 0.0055 0.8478 0.0132 0.052 Uiso 1 1 calc R . . C7_1 C 0.08400(16) 0.6948(3) 0.07126(19) 0.0500(7) Uani 1 1 d . . . H7A_1 H 0.1292 0.6477 0.0588 0.060 Uiso 1 1 calc R . . H7B_1 H 0.0465 0.6165 0.0728 0.060 Uiso 1 1 calc R . . C8_1 C 0.10577(17) 0.7681(3) 0.15760(19) 0.0546(8) Uani 1 1 d . . . H8A_1 H 0.0596 0.8054 0.1728 0.065 Uiso 1 1 calc R . . H8B_1 H 0.1285 0.6932 0.1999 0.065 Uiso 1 1 calc R . . C9_1 C 0.15926(15) 0.8910(3) 0.16133(16) 0.0410(6) Uani 1 1 d . . . C10_1 C 0.20094(14) 0.9926(3) 0.16133(15) 0.0364(6) Uani 1 1 d . . . C12_1 C 0.20666(15) 1.2654(3) 0.09587(15) 0.0386(6) Uani 1 1 d DU . . H12A_1 H 0.1538 1.2610 0.1017 0.046 Uiso 0.879(6) 1 calc PR A 1 H12B_1 H 0.2259 1.3661 0.1113 0.046 Uiso 0.879(6) 1 calc PR A 1 H12C_1 H 0.1722 1.3075 0.1287 0.046 Uiso 0.121(6) 1 calc PR A 2 H12D_1 H 0.2427 1.3452 0.0918 0.046 Uiso 0.121(6) 1 calc PR A 2 C13_1 C 0.2088(2) 1.2349(3) 0.00437(17) 0.0395(9) Uani 0.879(6) 1 d PDU A 1 H13A_1 H 0.2596 1.2586 -0.0041 0.047 Uiso 0.879(6) 1 calc PR A 1 H13B_1 H 0.1994 1.1288 -0.0078 0.047 Uiso 0.879(6) 1 calc PR A 1 C14_1 C 0.1506(2) 1.3248(3) -0.05624(18) 0.0385(9) Uani 0.879(6) 1 d PDU A 1 H14A_1 H 0.1524 1.4275 -0.0355 0.046 Uiso 0.879(6) 1 calc PR A 1 H14B_1 H 0.0999 1.2850 -0.0566 0.046 Uiso 0.879(6) 1 calc PR A 1 C15_1 C 0.16120(16) 1.3262(3) -0.14582(15) 0.0433(7) Uani 1 1 d DU . . H15A_1 H 0.2060 1.3874 -0.1469 0.052 Uiso 0.879(6) 1 calc PR A 1 H15B_1 H 0.1170 1.3761 -0.1816 0.052 Uiso 0.879(6) 1 calc PR A 1 H15C_1 H 0.1833 1.4062 -0.1737 0.052 Uiso 0.121(6) 1 calc PR A 2 H15D_1 H 0.1070 1.3474 -0.1514 0.052 Uiso 0.121(6) 1 calc PR A 2 C13B_1 C 0.1573(12) 1.253(3) 0.0057(9) 0.037(6) Uani 0.121(6) 1 d PDU A 2 H13C_1 H 0.1448 1.1487 -0.0087 0.044 Uiso 0.121(6) 1 calc PR A 2 H13D_1 H 0.1097 1.3086 0.0009 0.044 Uiso 0.121(6) 1 calc PR A 2 C14B_1 C 0.2019(13) 1.316(2) -0.0521(9) 0.036(6) Uani 0.121(6) 1 d PDU A 2 H14C_1 H 0.2478 1.2557 -0.0476 0.043 Uiso 0.121(6) 1 calc PR A 2 H14D_1 H 0.2183 1.4165 -0.0321 0.043 Uiso 0.121(6) 1 calc PR A 2 S1_2 S 0.75704(4) 0.28522(7) 0.12053(4) 0.0440(2) Uani 1 1 d . . . S2_2 S 0.65864(4) 0.45343(7) -0.23830(4) 0.03920(19) Uani 1 1 d . . . C2_2 C 0.68243(14) 0.3902(3) 0.12881(14) 0.0328(6) Uani 1 1 d . . . C3_2 C 0.63535(13) 0.4758(3) 0.13904(14) 0.0325(6) Uani 1 1 d . . . C4_2 C 0.58004(14) 0.5855(3) 0.15132(15) 0.0365(6) Uani 1 1 d . . . H4A_2 H 0.5915 0.6152 0.2113 0.044 Uiso 1 1 calc R . . H4B_2 H 0.5293 0.5401 0.1381 0.044 Uiso 1 1 calc R . . C5_2 C 0.57894(14) 0.7228(3) 0.09686(15) 0.0355(6) Uani 1 1 d . . . H5A_2 H 0.5443 0.7965 0.1122 0.043 Uiso 1 1 calc R . . H5B_2 H 0.6301 0.7665 0.1085 0.043 Uiso 1 1 calc R . . C6_2 C 0.55400(14) 0.6890(2) 0.00375(14) 0.0325(6) Uani 1 1 d . . . H6A_2 H 0.5020 0.6496 -0.0081 0.039 Uiso 1 1 calc R . . H6B_2 H 0.5871 0.6114 -0.0107 0.039 Uiso 1 1 calc R . . C7_2 C 0.55609(15) 0.8222(3) -0.05184(16) 0.0408(6) Uani 1 1 d . . . H7A_2 H 0.6086 0.8585 -0.0422 0.049 Uiso 1 1 calc R . . H7B_2 H 0.5251 0.9017 -0.0354 0.049 Uiso 1 1 calc R . . C8_2 C 0.52723(15) 0.7893(3) -0.14521(16) 0.0433(7) Uani 1 1 d . . . H8A_2 H 0.4741 0.7565 -0.1551 0.052 Uiso 1 1 calc R . . H8B_2 H 0.5283 0.8813 -0.1775 0.052 Uiso 1 1 calc R . . C9_2 C 0.57094(15) 0.6766(3) -0.17700(15) 0.0366(6) Uani 1 1 d . . . C10_2 C 0.60729(14) 0.5831(3) -0.20149(15) 0.0351(6) Uani 1 1 d . . . C12_2 C 0.64253(14) 0.2970(2) -0.17475(15) 0.0350(6) Uani 1 1 d . . . H12A_2 H 0.5879 0.2903 -0.1766 0.042 Uiso 1 1 calc R . . H12B_2 H 0.6574 0.2057 -0.1999 0.042 Uiso 1 1 calc R . . C13_2 C 0.68543(14) 0.3054(3) -0.08330(15) 0.0348(6) Uani 1 1 d . . . H13A_2 H 0.7400 0.2927 -0.0800 0.042 Uiso 1 1 calc R . . H13B_2 H 0.6779 0.4038 -0.0603 0.042 Uiso 1 1 calc R . . C14_2 C 0.65898(15) 0.1877(3) -0.03087(16) 0.0405(6) Uani 1 1 d . . . H14A_2 H 0.6132 0.2243 -0.0145 0.049 Uiso 1 1 calc R . . H14B_2 H 0.6443 0.0998 -0.0667 0.049 Uiso 1 1 calc R . . C15_2 C 0.71508(17) 0.1401(3) 0.04813(16) 0.0472(7) Uani 1 1 d . . . H15A_2 H 0.7563 0.0856 0.0311 0.057 Uiso 1 1 calc R . . H15B_2 H 0.6895 0.0702 0.0790 0.057 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 S1_1 0.0441(4) 0.0412(4) 0.0343(4) 0.0006(3) 0.0088(3) -0.0001(3) S2_1 0.0361(4) 0.0358(4) 0.0439(4) -0.0001(3) 0.0001(3) -0.0024(3) C2_1 0.0381(14) 0.0352(14) 0.0292(13) -0.0044(11) -0.0008(11) 0.0051(12) C3_1 0.0391(15) 0.0391(15) 0.0401(15) -0.0065(12) -0.0010(12) 0.0023(13) C4_1 0.0391(15) 0.0448(16) 0.0615(19) -0.0064(14) -0.0017(13) -0.0100(13) C5_1 0.0365(15) 0.0340(14) 0.070(2) -0.0055(14) 0.0046(14) -0.0105(12) C6_1 0.0392(15) 0.0297(13) 0.0614(18) 0.0005(12) 0.0109(13) -0.0040(12) C7_1 0.0412(16) 0.0322(14) 0.073(2) 0.0070(13) 0.0057(14) -0.0085(13) C8_1 0.0565(18) 0.0462(17) 0.060(2) 0.0153(14) 0.0112(15) -0.0094(15) C9_1 0.0425(15) 0.0366(15) 0.0419(16) 0.0067(12) 0.0056(12) 0.0019(13) C10_1 0.0362(14) 0.0363(14) 0.0347(14) 0.0011(11) 0.0041(11) 0.0057(12) C12_1 0.0489(16) 0.0301(13) 0.0317(14) 0.0010(11) -0.0016(12) 0.0002(12) C13_1 0.041(2) 0.0423(18) 0.0323(17) -0.0003(14) 0.0023(14) 0.0100(16) C14_1 0.040(2) 0.0323(17) 0.0398(19) 0.0005(13) 0.0026(15) 0.0066(16) C15_1 0.0575(17) 0.0345(14) 0.0328(14) 0.0025(11) -0.0008(13) -0.0060(13) C13B_1 0.041(15) 0.041(13) 0.026(7) -0.002(9) 0.003(8) -0.003(11) C14B_1 0.057(17) 0.022(11) 0.026(7) 0.000(9) 0.005(9) -0.009(12) S1_2 0.0395(4) 0.0412(4) 0.0451(4) -0.0050(3) -0.0033(3) 0.0103(3) S2_2 0.0480(4) 0.0386(4) 0.0329(4) -0.0035(3) 0.0133(3) -0.0054(3) C2_2 0.0378(14) 0.0311(13) 0.0269(13) -0.0011(10) 0.0020(11) -0.0045(12) C3_2 0.0334(13) 0.0345(13) 0.0269(13) -0.0042(10) 0.0012(10) -0.0028(12) C4_2 0.0350(14) 0.0438(14) 0.0300(14) -0.0068(11) 0.0059(11) 0.0019(12) C5_2 0.0344(14) 0.0323(13) 0.0384(15) -0.0096(11) 0.0052(11) 0.0027(11) C6_2 0.0330(13) 0.0277(12) 0.0358(14) -0.0033(10) 0.0061(11) -0.0016(11) C7_2 0.0474(16) 0.0266(13) 0.0507(17) 0.0013(11) 0.0158(13) 0.0062(12) C8_2 0.0474(16) 0.0398(15) 0.0439(16) 0.0167(12) 0.0129(13) 0.0123(13) C9_2 0.0429(15) 0.0356(14) 0.0314(14) 0.0093(11) 0.0084(12) -0.0022(13) C10_2 0.0402(14) 0.0343(14) 0.0287(13) 0.0058(11) 0.0037(11) -0.0078(12) C12_2 0.0415(14) 0.0275(12) 0.0344(14) -0.0048(10) 0.0053(11) -0.0025(11) C13_2 0.0357(14) 0.0312(13) 0.0359(14) -0.0036(11) 0.0048(11) -0.0022(11) C14_2 0.0499(16) 0.0284(13) 0.0413(15) -0.0035(11) 0.0062(12) -0.0048(12) C15_2 0.0706(19) 0.0279(13) 0.0402(15) -0.0017(11) 0.0067(14) 0.0100(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1_1 C2_1 1.692(3) . ? S1_1 C15_1 1.817(3) . ? S2_1 C10_1 1.692(3) . ? S2_1 C12_1 1.821(2) . ? C2_1 C3_1 1.193(3) . ? C3_1 C4_1 1.472(4) . ? C4_1 C5_1 1.525(4) . ? C5_1 C6_1 1.518(4) . ? C6_1 C7_1 1.517(4) . ? C7_1 C8_1 1.526(4) . ? C8_1 C9_1 1.473(4) . ? C9_1 C10_1 1.194(3) . ? C12_1 C13_1 1.528(4) . ? C12_1 C13B_1 1.544(15) . ? C13_1 C14_1 1.513(4) . ? C14_1 C15_1 1.517(4) . ? C15_1 C14B_1 1.543(15) . ? C13B_1 C14B_1 1.492(18) . ? S1_2 C2_2 1.690(3) . ? S1_2 C15_2 1.817(3) . ? S2_2 C10_2 1.696(3) . ? S2_2 C12_2 1.821(2) . ? C2_2 C3_2 1.197(3) . ? C3_2 C4_2 1.463(3) . ? C4_2 C5_2 1.528(3) . ? C5_2 C6_2 1.515(3) . ? C6_2 C7_2 1.517(3) . ? C7_2 C8_2 1.524(4) . ? C8_2 C9_2 1.462(4) . ? C9_2 C10_2 1.199(3) . ? C12_2 C13_2 1.521(3) . ? C13_2 C14_2 1.514(3) . ? C14_2 C15_2 1.514(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_1 S1_1 C15_1 104.26(12) . . ? C10_1 S2_1 C12_1 100.78(12) . . ? C3_1 C2_1 S1_1 171.0(2) . . ? C2_1 C3_1 C4_1 178.7(3) . . ? C3_1 C4_1 C5_1 114.2(2) . . ? C6_1 C5_1 C4_1 113.0(2) . . ? C7_1 C6_1 C5_1 113.7(2) . . ? C6_1 C7_1 C8_1 113.1(2) . . ? C9_1 C8_1 C7_1 113.5(2) . . ? C10_1 C9_1 C8_1 177.4(3) . . ? C9_1 C10_1 S2_1 176.3(2) . . ? C13_1 C12_1 C13B_1 36.3(8) . . ? C13_1 C12_1 S2_1 111.88(19) . . ? C13B_1 C12_1 S2_1 133.3(9) . . ? C14_1 C13_1 C12_1 111.8(3) . . ? C13_1 C14_1 C15_1 114.2(3) . . ? C14_1 C15_1 C14B_1 35.1(8) . . ? C14_1 C15_1 S1_1 117.58(19) . . ? C14B_1 C15_1 S1_1 107.5(9) . . ? C14B_1 C13B_1 C12_1 107.0(13) . . ? C13B_1 C14B_1 C15_1 116.2(15) . . ? C2_2 S1_2 C15_2 103.52(12) . . ? C10_2 S2_2 C12_2 99.53(11) . . ? C3_2 C2_2 S1_2 172.7(2) . . ? C2_2 C3_2 C4_2 177.5(2) . . ? C3_2 C4_2 C5_2 113.2(2) . . ? C6_2 C5_2 C4_2 112.29(19) . . ? C5_2 C6_2 C7_2 113.3(2) . . ? C6_2 C7_2 C8_2 113.1(2) . . ? C9_2 C8_2 C7_2 113.6(2) . . ? C10_2 C9_2 C8_2 178.7(3) . . ? C9_2 C10_2 S2_2 178.6(2) . . ? C13_2 C12_2 S2_2 113.98(16) . . ? C14_2 C13_2 C12_2 111.1(2) . . ? C15_2 C14_2 C13_2 116.3(2) . . ? C14_2 C15_2 S1_2 116.68(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.08 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.407 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.052 #===END data_hse16_(in_paper_5S25) _database_code_CSD 207501 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 S2' _chemical_formula_weight 252.42 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 9.1023(2) _cell_length_b 16.8216(3) _cell_length_c 9.1905(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1407.21(5) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.352 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8868 _exptl_absorpt_correction_T_max 0.9459 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13285 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1669 _reflns_number_gt 1382 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.4068P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1669 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.15791(4) 0.57408(2) 0.10741(4) 0.04329(15) Uani 1 1 d . . . C2 C 0.31124(16) 0.58455(8) 0.00602(15) 0.0364(3) Uani 1 1 d . . . C3 C 0.41288(17) 0.59091(8) -0.07483(15) 0.0402(3) Uani 1 1 d . A . C4 C 0.53478(19) 0.60084(10) -0.17777(18) 0.0503(4) Uani 1 1 d . . . H4A H 0.5387 0.5539 -0.2426 0.060 Uiso 0.764(6) 1 calc PR A 1 H4B H 0.6282 0.6029 -0.1227 0.060 Uiso 0.764(6) 1 calc PR A 1 H4C H 0.5039 0.5800 -0.2738 0.060 Uiso 0.236(6) 1 calc PR A 2 H4D H 0.6188 0.5683 -0.1441 0.060 Uiso 0.236(6) 1 calc PR A 2 C5 C 0.5220(3) 0.67461(13) -0.2695(3) 0.0464(7) Uani 0.764(6) 1 d P . 1 H5A H 0.4270 0.6740 -0.3218 0.056 Uiso 0.764(6) 1 calc PR A 1 H5B H 0.6016 0.6751 -0.3428 0.056 Uiso 0.764(6) 1 calc PR A 1 C6 C 0.5319(3) 0.7500 -0.1764(3) 0.0417(8) Uani 0.764(6) 2 d SP . 1 H6A H 0.4510 0.7500 -0.1043 0.050 Uiso 0.764(6) 2 calc SPR A 1 H6B H 0.6260 0.7500 -0.1224 0.050 Uiso 0.764(6) 2 calc SPR A 1 C7 C 0.21378(19) 0.7500 0.27543(19) 0.0314(4) Uani 1 2 d S . . H7A H 0.1267 0.7500 0.3399 0.038 Uiso 1 2 calc SR . . H7B H 0.1789 0.7500 0.1734 0.038 Uiso 1 2 calc SR . . C8 C 0.30455(14) 0.67565(8) 0.30334(14) 0.0356(3) Uani 1 1 d . . . H8A H 0.3882 0.6755 0.2346 0.043 Uiso 1 1 calc R . . H8B H 0.3457 0.6791 0.4028 0.043 Uiso 1 1 calc R . . C9 C 0.22437(16) 0.59715(8) 0.28919(15) 0.0406(3) Uani 1 1 d . . . H9A H 0.1396 0.5975 0.3566 0.049 Uiso 1 1 calc R . . H9B H 0.2913 0.5541 0.3207 0.049 Uiso 1 1 calc R . . C5B C 0.5859(10) 0.6854(5) -0.1965(11) 0.058(3) Uani 0.236(6) 1 d P . 2 H5B1 H 0.6694 0.6856 -0.2655 0.069 Uiso 0.236(6) 1 calc PR A 2 H5B2 H 0.6233 0.7046 -0.1017 0.069 Uiso 0.236(6) 1 calc PR A 2 C6B C 0.4596(9) 0.7500 -0.2565(9) 0.034(2) Uani 0.236(6) 2 d SP . 2 H6B1 H 0.4439 0.7500 -0.3630 0.041 Uiso 0.236(6) 2 calc SPR A 2 H6B2 H 0.3658 0.7500 -0.2018 0.041 Uiso 0.236(6) 2 calc SPR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0347(2) 0.0419(2) 0.0533(3) -0.00609(15) 0.00507(15) -0.00576(14) C2 0.0396(7) 0.0295(6) 0.0401(7) -0.0020(5) -0.0002(6) 0.0044(5) C3 0.0449(8) 0.0364(7) 0.0392(7) -0.0021(6) 0.0010(6) 0.0055(6) C4 0.0522(9) 0.0505(9) 0.0482(8) -0.0037(7) 0.0156(7) 0.0100(7) C5 0.0568(14) 0.0444(11) 0.0379(12) -0.0044(9) 0.0148(11) 0.0017(10) C6 0.0493(17) 0.0404(15) 0.0354(16) 0.000 0.0110(14) 0.000 C7 0.0260(8) 0.0344(9) 0.0338(9) 0.000 -0.0007(7) 0.000 C8 0.0309(6) 0.0410(7) 0.0348(6) 0.0023(5) -0.0018(5) 0.0052(5) C9 0.0440(8) 0.0363(7) 0.0413(8) 0.0091(6) 0.0088(6) 0.0053(6) C5B 0.048(5) 0.075(5) 0.051(5) -0.017(4) 0.018(4) -0.010(4) C6B 0.032(4) 0.051(5) 0.020(4) 0.000 0.001(3) 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 S1 C2 1.6873(15) . ? S1 C9 1.8186(15) . ? C2 C3 1.192(2) . ? C3 C4 1.468(2) . ? C4 C5 1.505(3) . ? C4 C5B 1.506(8) . ? C5 C6 1.532(3) . ? C6 C5 1.532(3) 7_575 ? C7 C8 1.5207(16) . ? C7 C8 1.5207(16) 7_575 ? C8 C9 1.514(2) . ? C5B C6B 1.675(13) . ? C6B C5B 1.675(13) 7_575 ? 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 S1 C9 102.12(7) . . ? C3 C2 S1 174.91(14) . . ? C2 C3 C4 177.83(16) . . ? C3 C4 C5 113.36(14) . . ? C3 C4 C5B 114.5(3) . . ? C5 C4 C5B 35.0(4) . . ? C4 C5 C6 111.4(2) . . ? C5 C6 C5 111.7(3) 7_575 . ? C8 C7 C8 110.66(15) . 7_575 ? C9 C8 C7 116.16(11) . . ? C8 C9 S1 115.17(9) . . ? C4 C5B C6B 116.0(7) . . ? C5B C6B C5B 80.9(8) 7_575 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.238 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.051 #===END data_hse20_(in_paper_7S23) _database_code_CSD 207502 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 S2' _chemical_formula_weight 252.42 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.4829(2) _cell_length_b 10.9233(2) _cell_length_c 9.01740(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.9720(10) _cell_angle_gamma 90.00 _cell_volume 1421.19(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.348 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8967 _exptl_absorpt_correction_T_max 0.9149 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14396 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _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 2.34 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3258 _reflns_number_gt 2831 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.3626P] 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 0.032(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3258 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0844 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.318 _refine_ls_shift/su_mean 0.017 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.01295(2) 0.06083(3) 0.22106(4) 0.04089(12) Uani 1 1 d . . . S2 S 0.74544(2) 0.42657(3) 0.22037(4) 0.03722(11) Uani 1 1 d . . . C2 C 0.93918(8) -0.03075(11) 0.30583(14) 0.0332(3) Uani 1 1 d . . . C3 C 0.88919(8) -0.09625(11) 0.36848(14) 0.0328(3) Uani 1 1 d . . . C4 C 0.82458(9) -0.17633(11) 0.43908(14) 0.0338(3) Uani 1 1 d . . . H4A H 0.7891 -0.1269 0.5065 0.041 Uiso 1 1 calc R . . H4B H 0.8604 -0.2382 0.5002 0.041 Uiso 1 1 calc R . . C5 C 0.75675(9) -0.24187(11) 0.32618(15) 0.0365(3) Uani 1 1 d . . . H5A H 0.7922 -0.2969 0.2649 0.044 Uiso 1 1 calc R . . H5B H 0.7148 -0.2934 0.3808 0.044 Uiso 1 1 calc R . . C6 C 0.69836(9) -0.15604(12) 0.22313(14) 0.0360(3) Uani 1 1 d . . . H6A H 0.7404 -0.1039 0.1694 0.043 Uiso 1 1 calc R . . H6B H 0.6612 -0.2058 0.1481 0.043 Uiso 1 1 calc R . . C7 C 0.63318(9) -0.07365(12) 0.30139(14) 0.0365(3) Uani 1 1 d . . . H7A H 0.6702 -0.0221 0.3747 0.044 Uiso 1 1 calc R . . H7B H 0.5917 -0.1253 0.3567 0.044 Uiso 1 1 calc R . . C8 C 0.57429(9) 0.00900(13) 0.19522(15) 0.0402(3) Uani 1 1 d . . . H8A H 0.6158 0.0642 0.1448 0.048 Uiso 1 1 calc R . . H8B H 0.5408 -0.0425 0.1178 0.048 Uiso 1 1 calc R . . C9 C 0.50403(9) 0.08632(13) 0.26961(17) 0.0436(3) Uani 1 1 d . . . H9A H 0.4607 0.0310 0.3161 0.052 Uiso 1 1 calc R . . H9B H 0.4675 0.1344 0.1921 0.052 Uiso 1 1 calc R . . C10 C 0.54685(9) 0.17423(12) 0.38839(15) 0.0381(3) Uani 1 1 d . . . H10A H 0.4967 0.2221 0.4289 0.046 Uiso 1 1 calc R . . H10B H 0.5781 0.1260 0.4711 0.046 Uiso 1 1 calc R . . C11 C 0.61398(8) 0.25896(11) 0.33168(14) 0.0322(3) Uani 1 1 d . . . C12 C 0.66925(8) 0.32570(11) 0.28272(14) 0.0309(3) Uani 1 1 d . . . C14 C 0.81442(8) 0.32769(11) 0.11104(13) 0.0310(3) Uani 1 1 d . . . H14A H 0.7725 0.2817 0.0386 0.037 Uiso 1 1 calc R . . H14B H 0.8552 0.3791 0.0541 0.037 Uiso 1 1 calc R . . C15 C 0.87374(8) 0.23735(11) 0.20562(12) 0.0291(2) Uani 1 1 d . . . H15A H 0.9149 0.2828 0.2797 0.035 Uiso 1 1 calc R . . H15B H 0.8331 0.1839 0.2604 0.035 Uiso 1 1 calc R . . C16 C 0.93197(8) 0.15895(11) 0.11107(13) 0.0308(3) Uani 1 1 d . . . H16A H 0.9671 0.2129 0.0480 0.037 Uiso 1 1 calc R . . H16B H 0.8904 0.1073 0.0443 0.037 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 S1 0.02495(17) 0.0423(2) 0.0556(2) 0.01026(15) 0.00436(14) 0.00302(12) S2 0.03306(18) 0.02300(16) 0.0564(2) 0.00260(13) 0.00850(14) -0.00128(11) C2 0.0313(6) 0.0304(6) 0.0374(6) 0.0000(5) -0.0003(5) 0.0059(5) C3 0.0322(6) 0.0303(6) 0.0356(6) 0.0002(5) 0.0000(5) 0.0065(5) C4 0.0375(6) 0.0317(6) 0.0329(6) 0.0024(5) 0.0075(5) 0.0060(5) C5 0.0435(7) 0.0277(6) 0.0402(7) -0.0050(5) 0.0140(5) -0.0022(5) C6 0.0370(7) 0.0414(7) 0.0300(6) -0.0064(5) 0.0055(5) -0.0079(5) C7 0.0383(7) 0.0395(7) 0.0317(6) 0.0011(5) 0.0029(5) 0.0009(5) C8 0.0415(7) 0.0395(7) 0.0379(7) 0.0047(6) -0.0070(5) -0.0080(6) C9 0.0274(6) 0.0421(7) 0.0598(9) 0.0138(6) -0.0044(6) -0.0051(5) C10 0.0303(6) 0.0384(7) 0.0469(7) 0.0104(6) 0.0110(5) 0.0037(5) C11 0.0276(6) 0.0311(6) 0.0380(6) 0.0019(5) 0.0033(5) 0.0053(5) C12 0.0273(6) 0.0289(6) 0.0363(6) 0.0022(5) 0.0012(5) 0.0036(5) C14 0.0308(6) 0.0311(6) 0.0313(6) 0.0052(5) 0.0036(5) -0.0012(5) C15 0.0321(6) 0.0309(6) 0.0243(5) 0.0024(4) 0.0028(4) 0.0009(5) C16 0.0301(6) 0.0340(6) 0.0285(6) 0.0024(5) 0.0041(4) -0.0005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.6934(13) . ? S1 C16 1.8183(12) . ? S2 C12 1.6898(12) . ? S2 C14 1.8187(12) . ? C2 C3 1.1942(18) . ? C3 C4 1.4661(17) . ? C4 C5 1.5299(18) . ? C5 C6 1.5236(19) . ? C6 C7 1.5213(18) . ? C7 C8 1.5223(18) . ? C8 C9 1.522(2) . ? C9 C10 1.529(2) . ? C10 C11 1.4661(17) . ? C11 C12 1.1951(17) . ? C14 C15 1.5206(15) . ? C15 C16 1.5153(16) . ? 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 S1 C16 101.07(6) . . ? C12 S2 C14 101.44(6) . . ? C3 C2 S1 178.14(11) . . ? C2 C3 C4 177.24(13) . . ? C3 C4 C5 112.80(10) . . ? C6 C5 C4 114.10(10) . . ? C7 C6 C5 114.52(10) . . ? C6 C7 C8 113.30(11) . . ? C9 C8 C7 114.29(11) . . ? C8 C9 C10 114.27(11) . . ? C11 C10 C9 113.14(11) . . ? C12 C11 C10 178.24(14) . . ? C11 C12 S2 176.61(12) . . ? C15 C14 S2 113.05(8) . . ? C16 C15 C14 111.48(9) . . ? C15 C16 S1 112.98(8) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.390 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.053 #===END data_hse18_(in_paper_7S25) _database_code_CSD 207503 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 S2' _chemical_formula_weight 280.47 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 4.5938(2) _cell_length_b 17.1826(9) _cell_length_c 9.9664(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.1660(10) _cell_angle_gamma 90.00 _cell_volume 785.48(7) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 3.00 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.322 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4454 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7873 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3532 _reflns_number_gt 3127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.0621P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(13) _refine_ls_number_reflns 3532 _refine_ls_number_parameters 164 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 S1 S 0.06178(12) -0.01093(3) 0.14999(6) 0.03851(16) Uani 1 1 d . . . S2 S 0.13644(10) 0.35316(3) 0.67039(5) 0.03606(15) Uani 1 1 d . . . C2 C -0.0867(4) 0.05236(12) 0.03651(19) 0.0295(4) Uani 1 1 d . . . C3 C -0.2034(5) 0.09556(11) -0.0439(2) 0.0296(4) Uani 1 1 d . . . C4 C -0.3544(5) 0.15019(12) -0.13948(19) 0.0293(4) Uani 1 1 d . . . H4A H -0.4886 0.1208 -0.2019 0.035 Uiso 1 1 calc R . . H4B H -0.2091 0.1768 -0.1932 0.035 Uiso 1 1 calc R . . C5 C -0.5303(5) 0.21202(12) -0.0625(2) 0.0306(4) Uani 1 1 d . . . H5A H -0.6537 0.2421 -0.1286 0.037 Uiso 1 1 calc R . . H5B H -0.6618 0.1846 -0.0028 0.037 Uiso 1 1 calc R . . C6 C -0.3431(5) 0.26834(12) 0.0212(2) 0.0306(4) Uani 1 1 d . . . H6A H -0.2133 0.2963 -0.0385 0.037 Uiso 1 1 calc R . . H6B H -0.2184 0.2384 0.0868 0.037 Uiso 1 1 calc R . . C7 C -0.5173(5) 0.32776(11) 0.0968(2) 0.0280(4) Uani 1 1 d . . . H7A H -0.6342 0.3597 0.0310 0.034 Uiso 1 1 calc R . . H7B H -0.6544 0.2999 0.1531 0.034 Uiso 1 1 calc R . . C8 C -0.3277(5) 0.38118(11) 0.1857(2) 0.0283(4) Uani 1 1 d . . . H8A H -0.1874 0.4080 0.1297 0.034 Uiso 1 1 calc R . . H8B H -0.2143 0.3493 0.2528 0.034 Uiso 1 1 calc R . . C9 C -0.5003(5) 0.44196(12) 0.2591(2) 0.0325(5) Uani 1 1 d . . . H9A H -0.6490 0.4152 0.3105 0.039 Uiso 1 1 calc R . . H9B H -0.6040 0.4758 0.1918 0.039 Uiso 1 1 calc R . . C10 C -0.3092(5) 0.49380(12) 0.3572(2) 0.0333(5) Uani 1 1 d . . . H10A H -0.1628 0.5218 0.3061 0.040 Uiso 1 1 calc R . . H10B H -0.4342 0.5330 0.3985 0.040 Uiso 1 1 calc R . . C11 C -0.1575(5) 0.44661(12) 0.4646(2) 0.0300(4) Uani 1 1 d . . . C12 C -0.0331(5) 0.40748(11) 0.5489(2) 0.0286(4) Uani 1 1 d . . . C14 C 0.3354(5) 0.28518(11) 0.5694(2) 0.0293(4) Uani 1 1 d . . . H14A H 0.4535 0.3151 0.5072 0.035 Uiso 1 1 calc R . . H14B H 0.4713 0.2548 0.6295 0.035 Uiso 1 1 calc R . . C15 C 0.1408(4) 0.22945(12) 0.4885(2) 0.0279(4) Uani 1 1 d . . . H15A H 0.0127 0.2595 0.4243 0.033 Uiso 1 1 calc R . . H15B H 0.0148 0.2014 0.5499 0.033 Uiso 1 1 calc R . . C16 C 0.3135(4) 0.17025(11) 0.4109(2) 0.0277(4) Uani 1 1 d . . . H16A H 0.4477 0.1982 0.3532 0.033 Uiso 1 1 calc R . . H16B H 0.4330 0.1381 0.4753 0.033 Uiso 1 1 calc R . . C17 C 0.1166(4) 0.11732(12) 0.3236(2) 0.0266(4) Uani 1 1 d . . . H17A H -0.0292 0.0929 0.3798 0.032 Uiso 1 1 calc R . . H17B H 0.0104 0.1489 0.2537 0.032 Uiso 1 1 calc R . . C18 C 0.2870(5) 0.05417(12) 0.2565(2) 0.0309(5) Uani 1 1 d . . . H18A H 0.3933 0.0230 0.3269 0.037 Uiso 1 1 calc R . . H18B H 0.4337 0.0790 0.2012 0.037 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 S1 0.0565(4) 0.0247(2) 0.0335(3) -0.0027(2) -0.0048(2) 0.0076(2) S2 0.0501(3) 0.0291(3) 0.0285(3) -0.0040(2) -0.0020(2) 0.0056(2) C2 0.0376(12) 0.0248(10) 0.0264(10) -0.0060(8) 0.0039(9) 0.0014(8) C3 0.0356(11) 0.0261(10) 0.0268(10) -0.0056(8) -0.0003(8) -0.0019(8) C4 0.0374(11) 0.0223(10) 0.0272(10) 0.0027(8) -0.0066(9) 0.0027(9) C5 0.0311(11) 0.0274(10) 0.0327(10) 0.0016(8) -0.0053(9) 0.0008(9) C6 0.0299(11) 0.0261(10) 0.0357(11) -0.0021(8) 0.0015(9) 0.0006(8) C7 0.0261(10) 0.0267(9) 0.0313(10) 0.0041(8) 0.0031(8) 0.0006(8) C8 0.0295(11) 0.0255(9) 0.0299(10) -0.0005(8) 0.0029(8) 0.0046(8) C9 0.0362(11) 0.0283(11) 0.0328(11) 0.0014(8) 0.0014(9) 0.0096(9) C10 0.0439(13) 0.0275(10) 0.0283(10) 0.0000(8) 0.0010(9) 0.0115(9) C11 0.0345(11) 0.0251(10) 0.0310(10) -0.0048(8) 0.0080(9) 0.0019(8) C12 0.0335(11) 0.0225(9) 0.0301(10) -0.0063(8) 0.0040(9) 0.0006(8) C14 0.0314(11) 0.0251(9) 0.0311(10) -0.0022(8) 0.0003(8) 0.0039(8) C15 0.0272(11) 0.0246(9) 0.0320(10) -0.0037(8) 0.0025(8) 0.0005(8) C16 0.0286(11) 0.0249(10) 0.0299(10) -0.0015(8) 0.0036(9) 0.0014(8) C17 0.0299(11) 0.0225(9) 0.0274(9) -0.0020(7) 0.0010(8) 0.0041(8) C18 0.0330(12) 0.0303(11) 0.0292(10) -0.0057(8) -0.0007(9) 0.0089(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 S1 C2 1.686(2) . ? S1 C18 1.824(2) . ? S2 C12 1.685(2) . ? S2 C14 1.821(2) . ? C2 C3 1.197(3) . ? C3 C4 1.482(3) . ? C4 C5 1.562(3) . ? C5 C6 1.514(3) . ? C6 C7 1.522(3) . ? C7 C8 1.517(3) . ? C8 C9 1.522(3) . ? C9 C10 1.557(3) . ? C10 C11 1.486(3) . ? C11 C12 1.196(3) . ? C14 C15 1.512(3) . ? C15 C16 1.527(3) . ? C16 C17 1.522(3) . ? C17 C18 1.515(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 S1 C18 100.97(9) . . ? C12 S2 C14 100.62(10) . . ? C3 C2 S1 177.2(2) . . ? C2 C3 C4 177.9(2) . . ? C3 C4 C5 110.58(16) . . ? C6 C5 C4 114.31(17) . . ? C5 C6 C7 113.78(17) . . ? C8 C7 C6 113.23(17) . . ? C7 C8 C9 113.46(17) . . ? C8 C9 C10 113.80(17) . . ? C11 C10 C9 111.47(17) . . ? C12 C11 C10 178.5(2) . . ? C11 C12 S2 178.57(19) . . ? C15 C14 S2 113.63(14) . . ? C14 C15 C16 112.55(15) . . ? C17 C16 C15 112.27(16) . . ? C18 C17 C16 112.04(16) . . ? C17 C18 S1 113.94(14) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.252 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.044 #===END data_hse23_(in_paper_5Se22) _database_code_CSD 207504 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 Se2' _chemical_formula_weight 304.14 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P-4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' _cell_length_a 15.4224(13) _cell_length_b 15.4224(13) _cell_length_c 4.8824(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1161.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 6.322 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0956 _exptl_absorpt_correction_T_max 0.5175 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2215 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 26.39 _reflns_number_total 1965 _reflns_number_gt 1666 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.1845P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(4) _refine_ls_number_reflns 1965 _refine_ls_number_parameters 137 _refine_ls_number_restraints 23 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.079 _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 Se1 Se 0.38432(4) 0.42737(4) 0.78566(17) 0.0401(2) Uani 1 1 d DU . . Se2 Se 0.34463(6) 0.14612(5) 1.1241(2) 0.0565(3) Uani 1 1 d DU . . C12 C 0.3833(6) 0.2452(5) 0.899(2) 0.034(2) Uani 0.743(14) 1 d PDU A 1 H12A H 0.4473 0.2459 0.8881 0.041 Uiso 0.743(14) 1 calc PR A 1 H12B H 0.3598 0.2399 0.7115 0.041 Uiso 0.743(14) 1 calc PR A 1 C13 C 0.3518(6) 0.3265(5) 1.0277(19) 0.030(2) Uani 0.743(14) 1 d PDU A 1 H13A H 0.3783 0.3337 1.2110 0.036 Uiso 0.743(14) 1 calc PR A 1 H13B H 0.2880 0.3242 1.0502 0.036 Uiso 0.743(14) 1 calc PR A 1 C2 C 0.2747(5) 0.4401(4) 0.6456(18) 0.0395(18) Uani 1 1 d . A . C3 C 0.2032(5) 0.4447(5) 0.558(2) 0.053(2) Uani 1 1 d . . . C4 C 0.1144(6) 0.4427(6) 0.450(3) 0.089(4) Uani 1 1 d . A . H4A H 0.0767 0.4769 0.5735 0.107 Uiso 1 1 calc R . . H4B H 0.1141 0.4716 0.2690 0.107 Uiso 1 1 calc R . . C5 C 0.0780(7) 0.3592(8) 0.420(3) 0.112(5) Uani 1 1 d . . . H5A H 0.0145 0.3676 0.4326 0.134 Uiso 1 1 calc R A . H5B H 0.0899 0.3421 0.2280 0.134 Uiso 1 1 calc R . . C6 C 0.0958(7) 0.2854(6) 0.577(4) 0.124(8) Uani 1 1 d . A . H6A H 0.1581 0.2746 0.5415 0.149 Uiso 1 1 calc R . . H6B H 0.0931 0.3071 0.7675 0.149 Uiso 1 1 calc R . . C7 C 0.0621(7) 0.2055(10) 0.595(4) 0.128(6) Uani 1 1 d . . . H7A H 0.0003 0.2161 0.6381 0.153 Uiso 1 1 calc R A . H7B H 0.0627 0.1845 0.4034 0.153 Uiso 1 1 calc R . . C8 C 0.0815(5) 0.1348(5) 0.741(3) 0.081(4) Uani 1 1 d . A . H8A H 0.0765 0.0835 0.6206 0.097 Uiso 1 1 calc R . . H8B H 0.0377 0.1284 0.8884 0.097 Uiso 1 1 calc R . . C9 C 0.1671(5) 0.1340(5) 0.866(2) 0.054(3) Uani 1 1 d . . . C10 C 0.2359(5) 0.1372(5) 0.9734(19) 0.0433(19) Uani 1 1 d . A . C12B C 0.3446(14) 0.2776(9) 1.097(5) 0.027(6) Uani 0.257(14) 1 d PDU A 2 H12C H 0.2844 0.2998 1.1030 0.033 Uiso 0.257(14) 1 calc PR A 2 H12D H 0.3773 0.3030 1.2516 0.033 Uiso 0.257(14) 1 calc PR A 2 C13B C 0.3857(14) 0.3013(9) 0.835(4) 0.021(6) Uani 0.257(14) 1 d PDU A 2 H13C H 0.3542 0.2733 0.6822 0.025 Uiso 0.257(14) 1 calc PR A 2 H13D H 0.4463 0.2802 0.8329 0.025 Uiso 0.257(14) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.0361(4) 0.0278(3) 0.0562(5) -0.0010(4) -0.0084(4) -0.0029(3) Se2 0.0620(6) 0.0473(5) 0.0602(6) 0.0198(4) -0.0184(5) -0.0168(4) C12 0.034(5) 0.032(5) 0.036(6) -0.005(4) 0.002(5) -0.001(4) C13 0.039(5) 0.034(4) 0.018(5) -0.003(4) -0.003(4) 0.003(5) C2 0.046(4) 0.027(3) 0.046(5) 0.002(3) 0.004(4) -0.003(3) C3 0.048(5) 0.034(4) 0.078(7) 0.003(4) -0.019(5) 0.001(4) C4 0.061(6) 0.061(6) 0.146(13) 0.009(7) -0.058(7) -0.004(5) C5 0.061(6) 0.153(11) 0.123(12) 0.065(10) -0.062(8) -0.028(7) C6 0.083(7) 0.047(5) 0.24(2) -0.015(9) -0.097(11) 0.009(5) C7 0.074(7) 0.195(15) 0.114(12) 0.065(12) -0.053(9) -0.081(9) C8 0.037(4) 0.052(5) 0.152(12) -0.014(7) -0.013(7) -0.014(4) C9 0.043(4) 0.038(4) 0.083(8) -0.015(5) 0.012(5) -0.007(3) C10 0.045(4) 0.042(4) 0.043(5) -0.003(4) 0.009(4) -0.006(3) C12B 0.007(10) 0.041(9) 0.034(15) -0.003(11) 0.006(10) 0.004(11) C13B 0.034(13) 0.016(7) 0.014(12) -0.006(8) 0.000(10) 0.017(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 C2 1.835(7) . ? Se1 C13B 1.959(13) . ? Se1 C13 2.017(8) . ? Se2 C10 1.836(9) . ? Se2 C12 1.973(8) . ? Se2 C12B 2.032(14) . ? C12 C13 1.484(11) . ? C2 C3 1.183(10) . ? C3 C4 1.469(11) . ? C4 C5 1.413(14) . ? C5 C6 1.399(17) . ? C6 C7 1.340(15) . ? C7 C8 1.338(16) . ? C8 C9 1.453(13) . ? C9 C10 1.184(11) . ? C12B C13B 1.472(19) . ? 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 Se1 C13B 99.3(7) . . ? C2 Se1 C13 94.1(4) . . ? C13B Se1 C13 33.4(6) . . ? C10 Se2 C12 96.4(4) . . ? C10 Se2 C12B 92.7(7) . . ? C12 Se2 C12B 36.0(7) . . ? C13 C12 Se2 108.7(6) . . ? C12 C13 Se1 108.9(6) . . ? C3 C2 Se1 177.2(7) . . ? C2 C3 C4 175.4(8) . . ? C5 C4 C3 115.3(8) . . ? C6 C5 C4 127.3(11) . . ? C7 C6 C5 135.0(12) . . ? C8 C7 C6 134.3(12) . . ? C7 C8 C9 115.7(8) . . ? C10 C9 C8 176.8(9) . . ? C9 C10 Se2 176.8(8) . . ? C13B C12B Se2 107.8(12) . . ? C12B C13B Se1 110.4(12) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.992 _refine_diff_density_min -0.742 _refine_diff_density_rms 0.106 #===END data_dwe91_(in_paper_5te23) _database_code_CSD 207505 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 Te2' _chemical_formula_weight 415.45 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' 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.8259(3) _cell_length_b 4.73160(10) _cell_length_c 14.5466(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.7260(10) _cell_angle_gamma 90.00 _cell_volume 656.99(3) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.100 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 4.404 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1775 _exptl_absorpt_correction_T_max 0.9171 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6353 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0657 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2966 _reflns_number_gt 2464 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0310P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(6) _refine_ls_number_reflns 2966 _refine_ls_number_parameters 127 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Te1 Te -0.16436(3) 0.30415(18) 0.69426(2) 0.02914(12) Uani 1 1 d . . . Te2 Te 0.35922(3) 0.30281(15) 0.52256(2) 0.02284(11) Uani 1 1 d . . . C2 C -0.0306(7) 0.4959(15) 0.8087(5) 0.0311(15) Uani 1 1 d . . . C3 C 0.0447(7) 0.6012(17) 0.8731(5) 0.0371(16) Uani 1 1 d . . . C4 C 0.1441(7) 0.747(3) 0.9532(5) 0.055(4) Uani 1 1 d . . . H4A H 0.1897 0.6032 0.9998 0.066 Uiso 1 1 calc R . . H4B H 0.0899 0.8744 0.9851 0.066 Uiso 1 1 calc R . . C5 C 0.2562(7) 0.9170(18) 0.9235(5) 0.0398(18) Uani 1 1 d . . . H5A H 0.3139 1.0117 0.9802 0.048 Uiso 1 1 calc R . . H5B H 0.2103 1.0664 0.8792 0.048 Uiso 1 1 calc R . . C6 C 0.3533(7) 0.7487(16) 0.8762(4) 0.030(2) Uani 1 1 d . . . H6A H 0.3969 0.5944 0.9191 0.036 Uiso 1 1 calc R . . H6B H 0.2968 0.6610 0.8177 0.036 Uiso 1 1 calc R . . C7 C 0.4688(7) 0.9270(15) 0.8511(5) 0.0372(17) Uani 1 1 d . . . H7A H 0.5222 1.0232 0.9089 0.045 Uiso 1 1 calc R . . H7B H 0.4255 1.0745 0.8051 0.045 Uiso 1 1 calc R . . C8 C 0.5702(6) 0.7512(19) 0.8086(4) 0.034(2) Uani 1 1 d . . . H8A H 0.6463 0.8761 0.7988 0.041 Uiso 1 1 calc R . . H8B H 0.6132 0.6044 0.8550 0.041 Uiso 1 1 calc R . . C9 C 0.5058(6) 0.6134(15) 0.7189(4) 0.0274(14) Uani 1 1 d . . . C10 C 0.4500(6) 0.5005(14) 0.6484(4) 0.0251(14) Uani 1 1 d . . . C12 C 0.2114(6) 0.0753(15) 0.5851(4) 0.0271(14) Uani 1 1 d . . . H12A H 0.1587 -0.0594 0.5377 0.033 Uiso 1 1 calc R . . H12B H 0.2647 -0.0365 0.6393 0.033 Uiso 1 1 calc R . . C13 C 0.1072(5) 0.260(2) 0.6193(4) 0.026(2) Uani 1 1 d . . . H13A H 0.0555 0.3797 0.5667 0.031 Uiso 1 1 calc R . . H13B H 0.1575 0.3855 0.6707 0.031 Uiso 1 1 calc R . . C14 C 0.0042(6) 0.0740(15) 0.6557(4) 0.0255(13) Uani 1 1 d . . . H14A H 0.0564 -0.0321 0.7117 0.031 Uiso 1 1 calc R . . H14B H -0.0368 -0.0657 0.6062 0.031 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 Te1 0.01885(17) 0.0332(2) 0.0400(2) 0.0074(5) 0.01616(14) 0.0003(5) Te2 0.01670(16) 0.02809(19) 0.02625(18) -0.0007(4) 0.01009(12) 0.0032(4) C2 0.032(4) 0.034(4) 0.032(4) 0.006(3) 0.018(3) 0.008(3) C3 0.033(4) 0.047(4) 0.036(4) 0.003(3) 0.017(3) 0.007(3) C4 0.036(3) 0.100(13) 0.033(3) -0.018(5) 0.018(3) 0.016(5) C5 0.046(4) 0.045(4) 0.028(4) -0.012(3) 0.008(3) -0.001(3) C6 0.033(3) 0.031(7) 0.027(3) -0.003(3) 0.008(2) 0.001(3) C7 0.048(4) 0.037(4) 0.026(3) -0.010(3) 0.008(3) -0.007(3) C8 0.029(3) 0.035(8) 0.041(3) -0.002(3) 0.014(3) -0.010(3) C9 0.017(3) 0.043(4) 0.027(3) 0.010(3) 0.014(2) -0.003(3) C10 0.014(3) 0.038(4) 0.026(3) 0.007(3) 0.009(2) 0.005(3) C12 0.016(3) 0.026(3) 0.041(4) 0.002(3) 0.010(3) 0.002(3) C13 0.018(2) 0.029(7) 0.034(3) 0.000(3) 0.013(2) 0.003(3) C14 0.022(3) 0.024(3) 0.033(3) 0.000(3) 0.011(3) -0.002(3) _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 Te1 C2 2.070(7) . ? Te1 C14 2.164(6) . ? Te2 C10 2.061(6) . ? Te2 C12 2.174(6) . ? C2 C3 1.160(9) . ? C3 C4 1.499(11) . ? C4 C5 1.507(11) . ? C5 C6 1.526(9) . ? C6 C7 1.526(9) . ? C7 C8 1.536(9) . ? C8 C9 1.462(9) . ? C9 C10 1.171(8) . ? C12 C13 1.517(9) . ? C13 C14 1.527(9) . ? 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 Te1 C14 92.9(2) . . ? C10 Te2 C12 92.5(2) . . ? C3 C2 Te1 179.4(7) . . ? C2 C3 C4 177.2(9) . . ? C3 C4 C5 114.2(6) . . ? C4 C5 C6 115.4(7) . . ? C7 C6 C5 113.5(6) . . ? C6 C7 C8 112.8(6) . . ? C9 C8 C7 114.6(5) . . ? C10 C9 C8 177.5(6) . . ? C9 C10 Te2 177.7(5) . . ? C13 C12 Te2 115.0(5) . . ? C12 C13 C14 109.6(8) . . ? C13 C14 Te1 114.2(5) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.935 _refine_diff_density_min -1.128 _refine_diff_density_rms 0.153 #===END #_eof End of Crystallographic Information File