#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/32/2203243.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_2203243 loop_ _publ_author_name 'G\"ultekin, Zeynep' 'Bayrak, Hacer' 'Frey, Wolfgang' 'H\"okelek, Tuncer' _publ_section_title ; 2,9-Bis(methoxymethyl)-1,3,8,10-tetrathiacyclotetradecane ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o157 _journal_page_last o159 _journal_paper_doi 10.1107/S1600536803029283 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H28 O2 S4' _chemical_formula_moiety 'C14 H28 O2 S4' _chemical_formula_sum 'C14 H28 O2 S4' _chemical_formula_weight 356.64 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.061(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 10.5512(10) _cell_length_b 10.4538(12) _cell_length_c 8.2152(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 18 _cell_measurement_theta_min 12 _cell_volume 905.98(17) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method 'non-profiled w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1619 _diffrn_reflns_theta_full 25.21 _diffrn_reflns_theta_max 25.21 _diffrn_reflns_theta_min 1.93 _diffrn_standards_decay_% 1 _diffrn_standards_interval_count 50 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.523 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.289 _refine_diff_density_min -0.426 _refine_ls_extinction_coef 0.13(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 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 92 _refine_ls_number_reflns 1497 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0495 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1005P)^2^+0.1736P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1315 _refine_ls_wR_factor_ref 0.1429 _reflns_number_gt 1262 _reflns_number_total 1497 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6208.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2203243 _cod_database_fobs_code 2203243 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' 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 0.20992(7) 0.03165(7) 0.26140(9) 0.0472(3) Uani d . 1 S S2 0.27180(7) 0.01049(7) 0.62716(9) 0.0481(3) Uani d . 1 S O1 0.48637(17) 0.2012(2) 0.5060(3) 0.0608(6) Uani d . 1 O C3 0.0513(3) -0.1625(3) 0.1723(3) 0.0544(8) Uani d . 1 C H3A 0.0301 -0.2523 0.1838 0.065 Uiso calc R 1 H H3B 0.0799 -0.1498 0.0619 0.065 Uiso calc R 1 H C2 0.1603(3) -0.1321(3) 0.2887(4) 0.0499(7) Uani d . 1 C H2A 0.2308 -0.1891 0.2684 0.060 Uiso calc R 1 H H2B 0.1339 -0.1449 0.4000 0.060 Uiso calc R 1 H C6 0.3746(2) 0.1881(3) 0.4115(4) 0.0477(7) Uani d . 1 C H6A 0.3915 0.2079 0.2986 0.057 Uiso calc R 1 H H6B 0.3108 0.2471 0.4496 0.057 Uiso calc R 1 H C4 -0.0689(3) -0.0840(3) 0.1952(3) 0.0503(7) Uani d . 1 C H4A -0.0477 0.0062 0.1902 0.060 Uiso calc R 1 H H4B -0.1279 -0.1023 0.1063 0.060 Uiso calc R 1 H C1 0.3267(2) 0.0511(3) 0.4256(3) 0.0433(6) Uani d . 1 C H1 0.3980 -0.0057 0.4020 0.052 Uiso calc R 1 H C5 -0.1329(3) -0.1110(3) 0.3546(3) 0.0490(7) Uani d . 1 C H5A -0.0743 -0.0942 0.4444 0.059 Uiso calc R 1 H H5B -0.1575 -0.2003 0.3591 0.059 Uiso calc R 1 H C7 0.5381(3) 0.3247(4) 0.4917(5) 0.0754(11) Uani d . 1 C H7A 0.6138 0.3308 0.5579 0.113 Uiso calc R 1 H H7B 0.4776 0.3868 0.5275 0.113 Uiso calc R 1 H H7C 0.5581 0.3409 0.3801 0.113 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 0.0578(5) 0.0468(5) 0.0370(5) -0.0069(3) -0.0034(3) 0.0067(3) S2 0.0561(5) 0.0504(5) 0.0377(6) -0.0003(3) -0.0037(3) 0.0116(3) O1 0.0546(11) 0.0474(11) 0.0797(16) -0.0066(9) -0.0170(11) 0.0058(11) C3 0.0729(17) 0.0526(15) 0.0381(17) -0.0120(14) 0.0116(13) -0.0118(13) C2 0.0593(15) 0.0442(14) 0.0465(17) -0.0003(12) 0.0078(12) 0.0025(12) C6 0.0471(12) 0.0488(15) 0.0471(16) -0.0018(11) 0.0029(11) 0.0095(12) C4 0.0604(15) 0.0599(17) 0.0303(15) -0.0155(13) -0.0031(11) 0.0008(13) C1 0.0441(12) 0.0451(13) 0.0408(16) 0.0032(10) 0.0009(10) 0.0012(11) C5 0.0638(15) 0.0491(15) 0.0341(15) 0.0006(12) 0.0052(11) 0.0040(12) C7 0.0740(19) 0.061(2) 0.091(3) -0.0213(16) -0.0032(19) 0.0064(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1230 '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_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 S1 C1 . . 101.97(13) yes C5 S2 C1 3_556 . 102.26(12) yes C6 O1 C7 . . 111.5(2) yes C2 C3 C4 . . 115.6(2) yes C2 C3 H3A . . 108.4 ? C4 C3 H3A . . 108.4 ? C2 C3 H3B . . 108.4 ? C4 C3 H3B . . 108.4 ? H3A C3 H3B . . 107.4 ? C3 C2 S1 . . 109.8(2) yes C3 C2 H2A . . 109.7 ? S1 C2 H2A . . 109.7 ? C3 C2 H2B . . 109.7 ? S1 C2 H2B . . 109.7 ? H2A C2 H2B . . 108.2 ? O1 C6 C1 . . 109.0(2) yes O1 C6 H6A . . 109.9 ? C1 C6 H6A . . 109.9 ? O1 C6 H6B . . 109.9 ? C1 C6 H6B . . 109.9 ? H6A C6 H6B . . 108.3 ? C5 C4 C3 . . 113.1(2) yes C5 C4 H4A . . 109.0 ? C3 C4 H4A . . 109.0 ? C5 C4 H4B . . 109.0 ? C3 C4 H4B . . 109.0 ? H4A C4 H4B . . 107.8 ? C6 C1 S2 . . 113.7(2) yes C6 C1 S1 . . 105.64(19) yes S2 C1 S1 . . 115.24(13) yes C6 C1 H1 . . 107.3 ? S2 C1 H1 . . 107.3 ? S1 C1 H1 . . 107.3 ? C4 C5 S2 . 3_556 109.8(2) yes C4 C5 H5A . . 109.7 ? S2 C5 H5A 3_556 . 109.7 ? C4 C5 H5B . . 109.7 ? S2 C5 H5B 3_556 . 109.7 ? H5A C5 H5B . . 108.2 ? O1 C7 H7A . . 109.5 ? O1 C7 H7B . . 109.5 ? H7A C7 H7B . . 109.5 ? O1 C7 H7C . . 109.5 ? H7A C7 H7C . . 109.5 ? H7B C7 H7C . . 109.5 ? 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 C2 . 1.805(3) yes S1 C1 . 1.821(3) yes S2 C5 3_556 1.812(3) yes S2 C1 . 1.815(3) yes O1 C6 . 1.406(3) yes O1 C7 . 1.407(4) yes C3 C2 . 1.517(4) yes C3 C4 . 1.525(4) yes C3 H3A . 0.9700 ? C3 H3B . 0.9700 ? C2 H2A . 0.9700 ? C2 H2B . 0.9700 ? C6 C1 . 1.524(4) yes C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? C4 C5 . 1.511(4) yes C4 H4A . 0.9700 ? C4 H4B . 0.9700 ? C1 H1 . 0.9800 ? C5 S2 3_556 1.812(3) yes C5 H5A . 0.9700 ? C5 H5B . 0.9700 ? C7 H7A . 0.9600 ? C7 H7B . 0.9600 ? C7 H7C . 0.9600 ? 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_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C4 C3 C2 S1 . . -62.0(3) yes C1 S1 C2 C3 . . 173.99(19) yes C7 O1 C6 C1 . . 177.4(3) yes C2 C3 C4 C5 . . -66.5(3) yes O1 C6 C1 S2 . . 67.4(2) yes O1 C6 C1 S1 . . -165.31(18) yes C5 S2 C1 C6 3_556 . 66.7(2) yes C5 S2 C1 S1 3_556 . -55.40(18) yes C2 S1 C1 C6 . . 179.82(18) yes C2 S1 C1 S2 . . -53.85(18) yes C3 C4 C5 S2 . 3_556 178.50(19) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139066452