#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/33/2003342.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2003342 loop_ _publ_author_name 'Adamson, A. J.' 'Banks, R. E.' 'Mothersdale, K. N.' 'Pritchard, R. G.' 'Manley, T.' 'Tipping, A. E.' _publ_section_title ; 2-(2,6-Difluorophenyl)-1,3-dithiane and 2-(2,6-Difluorophenyl)-1,3-dithiane 1,1,3,3-Tetraoxide. The Role of Oxidation in Locking a Molecular Conformation ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 772 _journal_page_last 775 _journal_paper_doi 10.1107/S0108270194011364 _journal_volume 51 _journal_year 1995 _chemical_compound_source 'Synthesized at UMIST' _chemical_formula_moiety ' C10 H10 F2 S2 ' _chemical_formula_structural ' C10 H10 F2 S2 ' _chemical_formula_sum 'C10 H10 F2 S2' _chemical_formula_weight 232.31 _chemical_melting_point 329.2(3) _chemical_name_systematic ; 2-(2,6-Difluorophenyl)-1,3-dithiane ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 83.57(2) _cell_angle_beta 84.65(2) _cell_angle_gamma 74.94(2) _cell_formula_units_Z 2 _cell_length_a 5.294(2) _cell_length_b 7.718(2) _cell_length_c 13.274(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 28.3 _cell_measurement_theta_min 20.1 _cell_volume 519.3(3) _computing_cell_refinement ' MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction ' TEXSAN PROCESS (Molecular Structure Corporation, 1985)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ' TEXSAN FINISH (Molecular Structure Corporation, 1985)' _computing_structure_refinement ' TEXSAN LS (Molecular Structure Corporation, 1985)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 296 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.02 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 3673 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% 'not significant' _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.48 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.485 _exptl_crystal_description plate _exptl_crystal_F_000 240.00 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.28 _refine_diff_density_min -0.24 _refine_ls_extinction_coef 111E-7(1) _refine_ls_extinction_method 'Zachariasen Type 2, Gaussian isotropic' _refine_ls_goodness_of_fit_obs 2.159 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 168 _refine_ls_number_reflns 1501 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.0297 _refine_ls_shift/esd_max 0.065 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'sigma; default TEXSAN' _refine_ls_wR_factor_obs 0.0343 _reflns_number_observed 1501 _reflns_number_total 1834 _reflns_observed_criterion I>3s(I) _cod_data_source_file ha1127.cif _cod_data_source_block U129zzz _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '329.0-329.5' was changed to '329.2(3)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 519.3(6) _cod_original_formula_sum ' C10 H10 F2 S2 ' _cod_database_code 2003342 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 S1 0.0657(3) -0.0167(2) 0.0101(2) 0.0399(3) -0.0021(2) 0.0474(3) C2 0.0319(9) -0.0067(7) -0.0042(8) 0.0373(9) -0.0018(8) 0.0436(10) S3 0.0465(3) -0.0161(2) 0.0043(2) 0.0474(3) -0.0011(2) 0.0438(3) C4 0.056(1) -0.0066(10) 0.000(1) 0.052(1) -0.0055(9) 0.041(1) C5 0.050(1) -0.0065(9) 0.0026(10) 0.044(1) -0.0116(9) 0.052(1) C6 0.056(1) -0.016(1) 0.010(1) 0.043(1) -0.0141(10) 0.065(1) C11 0.0366(9) -0.0136(8) -0.0012(7) 0.0377(9) -0.0010(7) 0.0382(9) C12 0.0430(10) -0.0135(8) -0.0013(9) 0.0384(9) -0.0018(8) 0.045(1) C13 0.055(1) -0.0146(10) 0.007(1) 0.043(1) -0.0084(9) 0.057(1) C14 0.076(2) -0.034(1) 0.012(1) 0.055(1) -0.0174(10) 0.053(1) C15 0.063(1) -0.038(1) -0.009(1) 0.073(1) -0.006(1) 0.046(1) C16 0.042(1) -0.0170(9) -0.0061(9) 0.053(1) 0.0011(9) 0.048(1) F12 0.0503(7) 0.0014(5) -0.0176(6) 0.0502(6) -0.0073(5) 0.0622(7) F16 0.0498(7) -0.0078(6) -0.0223(6) 0.0769(8) -0.0074(7) 0.0726(8) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv S1 0.55260(10) 0.19834(6) 0.78362(4) 0.0514(3) C2 0.5278(3) 0.4215(2) 0.7191(1) 0.038(1) S3 0.80223(9) 0.43273(6) 0.62734(4) 0.0458(3) C4 0.7498(5) 0.2792(3) 0.5426(2) 0.051(1) C5 0.7573(4) 0.0911(3) 0.5918(2) 0.049(1) C6 0.5404(4) 0.0833(3) 0.6740(2) 0.054(1) C11 0.4890(3) 0.5594(2) 0.7944(1) 0.036(1) C12 0.2657(3) 0.7022(2) 0.7959(1) 0.041(1) C13 0.2130(4) 0.8307(3) 0.8640(2) 0.051(1) C14 0.3905(5) 0.8183(3) 0.9355(2) 0.057(1) C15 0.6155(5) 0.6827(3) 0.9375(2) 0.056(1) C16 0.6605(4) 0.5578(3) 0.8672(2) 0.046(1) F12 0.0919(2) 0.7154(2) 0.72535(9) 0.055(1) F16 0.8846(2) 0.4234(2) 0.86959(10) 0.066(1) H2 0.383(4) 0.446(2) 0.679(1) 0.044(5) H4A 0.593(5) 0.325(3) 0.514(2) 0.070(7) H4B 0.884(5) 0.274(3) 0.493(2) 0.066(7) H5A 0.736(4) 0.016(3) 0.543(2) 0.057(6) H5B 0.920(4) 0.038(3) 0.625(2) 0.057(6) H6A 0.378(5) 0.132(3) 0.648(2) 0.065(7) H6B 0.558(4) -0.040(3) 0.699(2) 0.070(7) H13 0.061(5) 0.921(3) 0.855(2) 0.076(8) H14 0.342(4) 0.912(3) 0.982(2) 0.080(7) H15 0.732(4) 0.665(3) 0.984(2) 0.056(6) loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C 'International Tables' 0.002 0.002 H 'International Tables' 0.000 0.000 F 'International Tables' 0.014 0.010 S 'International Tables' 0.110 0.124 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 3 -1 -2 -2 -4 1 2 -5 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 S1 C6 97.80(10) yes S1 C2 S3 113.27(9) yes S1 C2 C11 110.90(10) ? S3 C2 C11 111.50(10) ? C2 S3 C4 97.70(10) yes S3 C4 C5 114.6(2) yes C4 C5 C6 114.1(2) yes S1 C6 C5 114.7(2) yes C2 C11 C12 120.6(2) ? C2 C11 C16 125.2(2) ? C12 C11 C16 114.2(2) ? C11 C12 C13 124.0(2) ? C11 C12 F12 117.7(2) ? C13 C12 F12 118.3(2) ? C12 C13 C14 118.4(2) ? C13 C14 C15 120.6(2) ? C14 C15 C16 118.9(2) ? C11 C16 C15 123.9(2) ? C11 C16 F16 117.6(2) ? C15 C16 F16 118.5(2) ? S1 C2 H2 106.0(10) ? S3 C2 H2 104.0(10) ? C11 C2 H2 111.0(10) ? S3 C4 H4A 110.0(10) ? S3 C4 H4B 105.0(10) ? C5 C4 H4A 109.0(10) ? C5 C4 H4B 109.0(10) ? H4A C4 H4B 109(2) ? C4 C5 H5A 110.0(10) ? C4 C5 H5B 111.0(10) ? C6 C5 H5A 105.0(10) ? C6 C5 H5B 105.0(10) ? H5A C5 H5B 110(2) ? S1 C6 H6A 107.0(10) ? S1 C6 H6B 105.0(10) ? C5 C6 H6A 111.0(10) ? C5 C6 H6B 108.0(10) ? H6A C6 H6B 111(2) ? C12 C13 H13 116(2) ? C14 C13 H13 126(2) ? C13 C14 H14 115.0(10) ? C15 C14 H14 125.0(10) ? C14 C15 H15 124.0(10) ? C16 C15 H15 117.0(10) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C2 1.814(2) yes S1 C6 1.802(2) yes C2 S3 1.821(2) yes C2 C11 1.503(2) yes S3 C4 1.809(2) yes C4 C5 1.516(3) yes C5 C6 1.517(3) yes C11 C12 1.392(3) ? C11 C16 1.383(3) ? C12 C13 1.374(3) ? C12 F12 1.351(2) ? C13 C14 1.375(3) ? C14 C15 1.366(3) ? C15 C16 1.378(3) ? C16 F16 1.358(2) ? C2 H2 0.94(2) ? C4 H4A 0.91(3) ? C4 H4B 0.92(2) ? C5 H5A 0.95(2) ? C5 H5B 0.97(2) ? C6 H6A 0.93(2) ? C6 H6B 0.96(2) ? C13 H13 0.92(2) ? C14 H14 0.97(2) ? C15 H15 0.89(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 101920529