#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/32/2203265.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_2203265 loop_ _publ_author_name 'Brewer, A. David' 'Ferguson, George' 'Lough, Alan J.' 'Strunk, Richard J.' _publ_section_title ; 2,3-Dihydro-5,6-dimethyl-1,4-dithiine 1,1,4-trioxide ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o392 _journal_page_last o394 _journal_paper_doi 10.1107/S1600536804003356 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C6 H10 O3 S2' _chemical_formula_moiety 'C6 H10 O3 S2' _chemical_formula_sum 'C6 H10 O3 S2' _chemical_formula_weight 194.28 _space_group_IT_number 18 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2 2ab' _symmetry_space_group_name_H-M 'P 21 21 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 5.5919(5) _cell_length_b 9.2507(10) _cell_length_c 7.9146(9) _cell_measurement_reflns_used 761 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 25.45 _cell_measurement_theta_min 2.57 _cell_volume 409.41(7) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and PLATON (Spek, 2002)' _computing_publication_material 'SHELXL97 and WordPerfect macro PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150.0(10) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0762 _diffrn_reflns_av_sigmaI/netI 0.0549 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 3121 _diffrn_reflns_theta_full 25.45 _diffrn_reflns_theta_max 25.45 _diffrn_reflns_theta_min 2.57 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.604 _exptl_absorpt_correction_type none _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 204 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.271 _refine_diff_density_min -0.288 _refine_ls_abs_structure_details 'Flack (1983), 287 Friedel pairs' _refine_ls_abs_structure_Flack 0.4(3) _refine_ls_extinction_coef 0.09(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 58 _refine_ls_number_reflns 761 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.159 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0562 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0563P)^2^+0.467P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1363 _refine_ls_wR_factor_ref 0.1432 _reflns_number_gt 672 _reflns_number_total 761 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6407.cif _cod_data_source_block I _cod_database_code 2203265 _cod_database_fobs_code 2203265 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol S1 0.7090(2) 0.36431(15) 0.80083(19) 0.0466(5) Uani d . 1 S O1 0.9651(13) 0.3655(11) 0.7621(11) 0.073(3) Uani d P 0.50 O O2 0.5815(9) 0.2289(4) 0.8227(6) 0.0657(14) Uani d . 1 O C1 0.5848(9) 0.4496(5) 0.6167(7) 0.0388(13) Uani d . 1 C C2 0.6317(10) 0.4823(6) 0.9686(7) 0.0470(14) Uani d . 1 C C3 0.6853(14) 0.3898(7) 0.4581(8) 0.0669(18) Uani d . 1 C H2A 0.6747 0.4365 1.0775 0.056 Uiso calc R 1 H H2B 0.7249 0.5729 0.9581 0.056 Uiso calc R 1 H H3A 0.5545 0.3604 0.3832 0.100 Uiso calc R 1 H H3B 0.7852 0.3057 0.4843 0.100 Uiso calc R 1 H H3C 0.7826 0.4637 0.4020 0.100 Uiso calc R 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0502(8) 0.0419(8) 0.0476(8) 0.0083(6) -0.0123(6) -0.0111(6) O1 0.030(3) 0.103(7) 0.085(6) 0.023(4) -0.020(4) -0.053(6) O2 0.096(4) 0.037(2) 0.064(3) 0.0007(19) -0.029(3) 0.005(2) C1 0.044(3) 0.038(3) 0.035(3) 0.001(2) 0.000(2) -0.010(2) C2 0.069(4) 0.043(3) 0.029(2) 0.007(3) -0.014(2) -0.007(2) C3 0.089(5) 0.065(4) 0.047(3) -0.001(4) 0.014(3) -0.020(3) 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' O O 0.0106 0.0060 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle _geom_angle_publ_flag O1 S1 O2 . 120.8(5) yes O1 S1 C1 . 101.8(4) yes O1 S1 C2 . 113.0(4) yes O2 S1 C1 . 106.6(3) yes O2 S1 C2 . 108.8(3) yes C1 S1 C2 . 104.1(2) yes C1 C1 S1 2_665 125.70(16) yes C1 C1 C3 2_665 122.2(4) yes C3 C1 S1 . 112.1(4) yes C2 C2 S1 2_665 111.8(4) yes C2 C2 H2A 2_665 109.3 no S1 C2 H2A . 109.3 no C2 C2 H2B 2_665 109.3 no S1 C2 H2B . 109.3 no H2A C2 H2B . 107.9 no C1 C3 H3A . 109.5 no C1 C3 H3B . 109.5 no H3A C3 H3B . 109.5 no C1 C3 H3C . 109.5 no H3A C3 H3C . 109.5 no H3B C3 H3C . 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O1 . 1.464(8) yes S1 O2 . 1.451(5) yes S1 C1 . 1.797(5) yes S1 C2 . 1.772(5) yes C1 C1 2_665 1.330(10) yes C1 C3 . 1.482(7) yes C2 C2 2_665 1.509(11) yes C2 H2A . 0.99 no C2 H2B . 0.99 no C3 H3A . 0.98 no C3 H3B . 0.98 no C3 H3C . 0.98 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C2 H2B O1 2_765 0.99 2.40 3.120(10) 130 yes C2 H2B O2 4_657 0.99 2.50 3.241(7) 131 yes C3 H3A O1 3_456 0.98 2.44 3.183(11) 133 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 S1 C1 C1 2_665 96.5(7) no O1 S1 C1 C1 2_665 -136.1(7) no C2 S1 C1 C1 2_665 -18.5(8) no O2 S1 C1 C3 . -80.8(5) no O1 S1 C1 C3 . 46.7(6) no C2 S1 C1 C3 . 164.3(4) no O2 S1 C2 C2 2_665 -62.0(5) no O1 S1 C2 C2 2_665 160.9(6) no C1 S1 C2 C2 2_665 51.3(6) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 41385