#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/67/2206730.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_2206730 loop_ _publ_author_name 'Ga\"el Labat' 'Joan Halfpenny' _publ_section_title ; 1,2-Bis(3-thienyloxy)ethane: a thiophene-based precursor for thiophene-based azacryptand Mannich bases ; _journal_coeditor_code IS6112 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2815 _journal_page_last o2816 _journal_paper_doi 10.1107/S1600536805024529 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C10 H10 O2 S2' _chemical_formula_moiety 'C10 H10 O2 S2' _chemical_formula_sum 'C10 H10 O2 S2' _chemical_formula_weight 226.30 _chemical_name_systematic ; 1,2-Bis(3-thienyloxy)ethane ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/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 111.362(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 22.175(3) _cell_length_b 5.3918(4) _cell_length_c 9.0831(11) _cell_measurement_reflns_used 9090 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 29.55 _cell_measurement_theta_min 1.925 _cell_volume 1011.4(2) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 153(2) _diffrn_detector_area_resol_mean 0.81\%A _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Stoe IPDS-II' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 9441 _diffrn_reflns_theta_full 29.41 _diffrn_reflns_theta_max 29.41 _diffrn_reflns_theta_min 1.97 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.494 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.354 _refine_diff_density_min -0.351 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 64 _refine_ls_number_reflns 1398 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0312 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0472P)^2^+1.0038P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0882 _refine_ls_wR_factor_ref 0.0895 _reflns_number_gt 1302 _reflns_number_total 1398 _reflns_threshold_expression I>2\s(I) _cod_data_source_file is6112.cif _cod_data_source_block I _cod_original_cell_volume 1011.39(19) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2206730 _cod_database_fobs_code 2206730 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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_occupancy _atom_site_type_symbol S1 0.705495(15) 0.30108(6) 0.11836(4) 0.02820(13) Uani d 1 S O1 0.53539(5) 0.28858(18) 0.14777(11) 0.0259(2) Uani d 1 O C3 0.59883(6) 0.0614(2) 0.02934(16) 0.0261(3) Uani d 1 C H3 0.5630 -0.0585 -0.0223 0.050 Uiso d 1 H C2 0.59236(6) 0.2606(2) 0.12527(14) 0.0216(2) Uani d 1 C C4 0.65818(7) 0.0611(2) 0.01542(16) 0.0282(3) Uani d 1 C H4 0.6733 -0.0522 -0.0426 0.050 Uiso d 1 H C5 0.53252(6) 0.4969(2) 0.24223(15) 0.0247(3) Uani d 1 C H5A 0.5691 0.4837 0.3545 0.050 Uiso d 1 H H5B 0.5403 0.6558 0.1910 0.050 Uiso d 1 H C1 0.64618(6) 0.4075(2) 0.18219(14) 0.0236(2) Uani d 1 C H1 0.6573 0.5546 0.2544 0.050 Uiso d 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 0.02423(18) 0.0307(2) 0.0318(2) -0.00172(11) 0.01271(14) -0.00265(12) O1 0.0246(4) 0.0290(5) 0.0272(5) -0.0060(3) 0.0133(4) -0.0087(3) C3 0.0301(6) 0.0217(5) 0.0275(6) -0.0026(5) 0.0119(5) -0.0034(5) C2 0.0240(5) 0.0222(5) 0.0194(5) -0.0016(4) 0.0091(4) 0.0006(4) C4 0.0323(6) 0.0231(6) 0.0306(6) 0.0008(5) 0.0132(5) -0.0032(5) C5 0.0280(6) 0.0258(6) 0.0224(5) -0.0027(5) 0.0118(5) -0.0040(4) C1 0.0245(5) 0.0252(6) 0.0222(5) -0.0031(4) 0.0098(4) -0.0023(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_site_symmetry_3 _geom_angle _geom_angle_publ_flag C4 S1 C1 . . 92.55(6) y C2 O1 C5 . . 115.12(10) y C4 C3 C2 . . 111.88(11) y C4 C3 H3 . . 125.7 ? C2 C3 H3 . . 122.4 ? C1 C2 O1 . . 127.57(12) y C1 C2 C3 . . 113.59(12) y O1 C2 C3 . . 118.83(11) y C3 C4 S1 . . 111.56(10) y C3 C4 H4 . . 127.0 ? S1 C4 H4 . . 121.5 ? O1 C5 C5 . 2_655 108.13(9) y O1 C5 H5A . . 110.0 ? C5 C5 H5A 2_655 . 109.8 ? O1 C5 H5B . . 109.6 ? C5 C5 H5B 2_655 . 111.8 ? H5A C5 H5B . . 107.5 ? C2 C1 S1 . . 110.43(10) y C2 C1 H1 . . 132.8 ? S1 C1 H1 . . 116.7 ? 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 C4 . 1.7129(14) y S1 C1 . 1.7178(13) y O1 C2 . 1.3597(15) y O1 C5 . 1.4288(15) y C3 C4 . 1.3674(19) y C3 C2 . 1.4227(17) y C3 H3 . 0.9989 ? C2 C1 . 1.3672(17) y C4 H4 . 0.9445 ? C5 C5 2_655 1.500(2) y C5 H5A . 1.0489 ? C5 H5B . 1.0193 ? C1 H1 . 1.0012 ? 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 C3 H3 O1 5_655 1.00 2.41 3.3940(16) 170 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 C5 O1 C2 C1 . 0.00(18) C5 O1 C2 C3 . -178.45(11) C4 C3 C2 C1 . 0.06(17) C4 C3 C2 O1 . 178.73(12) C2 C3 C4 S1 . 0.05(15) C1 S1 C4 C3 . -0.11(11) C2 O1 C5 C5 2_655 -178.84(11) O1 C2 C1 S1 . -178.66(10) C3 C2 C1 S1 . -0.14(14) C4 S1 C1 C2 . 0.14(10) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 10585353