#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011305.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_2011305 loop_ _publ_author_name 'Boryczka, Stanis\/law' 'Steiner, Thomas' _publ_section_title ; Hydrogen bonding in two salts of 3-methylthio-4-(propargylthio)quinoline ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1139 _journal_page_last 1141 _journal_paper_doi 10.1107/S0108270100008271 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C13 H12 N S2 + , C2 Cl3 O2 -' _chemical_formula_sum 'C15 H12 Cl3 N O2 S2' _chemical_formula_weight 408.73 _chemical_name_systematic ; 4-Methylthio-3-propargylthioquinolinium trichloroacetate ; _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' _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 111.67(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 19.430(11) _cell_length_b 5.338(3) _cell_length_c 36.66(3) _cell_measurement_reflns_used 26 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 15.1 _cell_measurement_theta_min 5.0 _cell_volume 3534(4) _computing_cell_refinement 'please provide details' _computing_data_collection 'please provide details' _computing_data_reduction 'please provide details' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293 _diffrn_measured_fraction_theta_full .994 _diffrn_measured_fraction_theta_max .994 _diffrn_measurement_device_type 'STOE four-circle' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .032 _diffrn_reflns_av_sigmaI/netI .042 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 2 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_number 4098 _diffrn_reflns_theta_full 27.54 _diffrn_reflns_theta_max 27.54 _diffrn_reflns_theta_min 2.13 _diffrn_standards_decay_% 6 _diffrn_standards_interval_time 90 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .761 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1664 _exptl_crystal_size_max 1.2 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .05 _refine_diff_density_max .56 _refine_diff_density_min -.43 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 224 _refine_ls_number_reflns 4031 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.011 _refine_ls_R_factor_all .093 _refine_ls_R_factor_gt .056 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0764P)^2^+5.2477P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .165 _reflns_number_gt 2781 _reflns_number_total 4031 _reflns_threshold_expression I>2\s(I) _cod_data_source_file de1147.cif _cod_data_source_block III _cod_original_cell_volume 3533(4) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2011305 _cod_database_fobs_code 2011305 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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 .14430(6) .3416(2) .03462(3) .0626(3) Uani d . 1 . . S S2 .05253(5) -.00203(18) .07042(3) .0556(3) Uani d . 1 . . S N1 .19773(15) .6183(5) .14213(8) .0412(6) Uani d . 1 . . N H1 .230(2) .741(9) .1550(12) .066(13) Uiso d . 1 . . H C2 .19199(18) .5839(7) .10568(10) .0440(8) Uani d . 1 . . C H2 .2172 .6907 .0949 .053(11) Uiso calc R 1 . . H C3 .14879(18) .3902(7) .08256(9) .0422(7) Uani d . 1 . . C C4 .10912(16) .2401(6) .09870(9) .0393(7) Uani d . 1 . . C C5 .11634(16) .2755(6) .13815(9) .0385(7) Uani d . 1 . . C C6 .08055(19) .1282(7) .15765(11) .0487(8) Uani d . 1 . . C H6 .0490 .0004 .1441 .041(9) Uiso calc R 1 . . H C7 .0912(2) .1687(8) .19567(12) .0555(9) Uani d . 1 . . C H7 .0672 .0673 .2079 .047(10) Uiso calc R 1 . . H C8 .1381(2) .3624(8) .21719(11) .0560(10) Uani d . 1 . . C H8 .1450 .3878 .2434 .044(9) Uiso calc R 1 . . H C9 .1730(2) .5116(7) .19942(10) .0485(8) Uani d . 1 . . C H9 .2036 .6407 .2134 .064(12) Uiso calc R 1 . . H C10 .16300(17) .4708(6) .15992(9) .0391(7) Uani d . 1 . . C C11 .2164(3) .5331(15) .03144(14) .093(2) Uani d . 1 . . C H11A .2043 .7061 .0330 .12(3) Uiso calc R 1 . . H H11B .2222 .5030 .0069 .085(15) Uiso calc R 1 . . H H11C .2619 .4940 .0527 .089(17) Uiso calc R 1 . . H C12 -.0253(2) .1809(10) .03786(11) .0626(11) Uani d . 1 . . C H12A -.0070 .3007 .0237 .103(19) Uiso calc R 1 . . H H12B -.0593 .0694 .0187 .078(14) Uiso calc R 1 . . H C13 -.0650(2) .3139(9) .05824(11) .0587(10) Uani d . 1 . . C C14 -.0958(3) .4239(12) .07467(14) .0821(15) Uani d . 1 . . C H14 -.1206 .5125 .0879 .12(2) Uiso calc R 1 . . H Cl1 .45966(6) 1.0717(2) .18929(4) .0824(4) Uani d . 1 . . Cl Cl2 .38600(6) 1.48057(19) .14004(3) .0650(3) Uani d . 1 . . Cl Cl3 .37079(7) 1.4117(2) .21391(3) .0720(3) Uani d . 1 . . Cl O1 .28681(14) .9747(5) .17708(7) .0529(6) Uani d . 1 . . O O2 .29272(14) 1.0461(5) .11853(7) .0526(6) Uani d . 1 . . O C15 .37879(18) 1.2549(6) .17346(11) .0450(8) Uani d . 1 . . C C16 .31214(17) 1.0752(6) .15390(10) .0401(7) Uani d . 1 . . C 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 .0676(6) .0760(7) .0439(5) -.0172(6) .0204(4) -.0110(5) S2 .0545(5) .0417(5) .0617(6) -.0104(4) .0109(4) -.0133(4) N1 .0384(14) .0362(15) .0450(15) -.0057(12) .0107(12) -.0053(12) C2 .0412(16) .0423(18) .0448(18) -.0067(15) .0114(14) -.0011(15) C3 .0392(16) .0425(18) .0389(16) -.0012(14) .0074(13) -.0010(14) C4 .0350(15) .0309(16) .0443(17) .0000(13) .0057(13) -.0027(13) C5 .0329(15) .0319(16) .0451(17) .0009(12) .0076(13) .0021(13) C6 .0449(18) .042(2) .053(2) -.0041(15) .0120(16) .0064(16) C7 .058(2) .051(2) .058(2) -.0021(19) .0221(18) .0125(18) C8 .060(2) .063(3) .0437(19) .009(2) .0181(17) .0079(18) C9 .0476(18) .047(2) .0462(18) .0001(16) .0118(15) -.0052(16) C10 .0372(15) .0324(16) .0430(17) .0016(13) .0093(13) .0004(13) C11 .084(3) .146(6) .056(3) -.049(4) .034(3) -.014(3) C12 .048(2) .084(3) .045(2) -.001(2) .0040(17) -.015(2) C13 .056(2) .068(3) .047(2) .001(2) .0125(18) -.0025(19) C14 .088(3) .099(4) .063(3) .021(3) .032(3) .000(3) Cl1 .0443(5) .0486(6) .1277(11) .0074(4) .0008(6) -.0085(6) Cl2 .0676(6) .0463(5) .0811(7) -.0163(5) .0277(5) .0020(5) Cl3 .0928(8) .0537(6) .0637(6) -.0126(6) .0223(6) -.0244(5) O1 .0593(15) .0478(15) .0528(14) -.0168(12) .0221(12) -.0088(12) O2 .0579(15) .0476(15) .0467(14) -.0133(12) .0128(12) -.0049(11) C15 .0406(17) .0313(16) .056(2) -.0007(14) .0092(15) -.0054(14) C16 .0362(15) .0278(15) .0512(19) -.0001(13) .0102(14) -.0056(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 '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 _geom_angle_publ_flag C3 S1 C11 103.5(2) y C4 S2 C12 100.27(19) y C2 N1 C10 122.7(3) y C2 N1 H1 115(3) ? C10 N1 H1 123(3) ? N1 C2 C3 121.7(3) ? N1 C2 H2 119.1 ? C3 C2 H2 119.1 ? C4 C3 C2 118.1(3) ? C4 C3 S1 120.9(3) y C2 C3 S1 120.9(3) y C3 C4 C5 119.9(3) ? C3 C4 S2 119.8(3) y C5 C4 S2 120.3(3) y C6 C5 C4 124.4(3) ? C6 C5 C10 117.3(3) ? C4 C5 C10 118.4(3) ? C7 C6 C5 121.3(4) ? C7 C6 H6 119.3 ? C5 C6 H6 119.3 ? C6 C7 C8 121.0(4) ? C6 C7 H7 119.5 ? C8 C7 H7 119.5 ? C9 C8 C7 119.7(4) ? C9 C8 H8 120.1 ? C7 C8 H8 120.1 ? C8 C9 C10 120.0(3) ? C8 C9 H9 120.0 ? C10 C9 H9 120.0 ? N1 C10 C9 120.2(3) ? N1 C10 C5 119.1(3) ? C9 C10 C5 120.7(3) ? S1 C11 H11A 109.5 ? S1 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? S1 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? C13 C12 S2 113.4(3) ? C13 C12 H12A 108.9 ? S2 C12 H12A 108.9 ? C13 C12 H12B 108.9 ? S2 C12 H12B 108.9 ? H12A C12 H12B 107.7 ? C14 C13 C12 178.7(5) ? C13 C14 H14 180.0 ? C16 C15 Cl1 107.4(2) ? C16 C15 Cl3 111.3(2) ? Cl1 C15 Cl3 109.4(2) ? C16 C15 Cl2 111.6(2) ? Cl1 C15 Cl2 108.6(2) ? Cl3 C15 Cl2 108.39(19) ? O2 C16 O1 128.6(3) ? O2 C16 C15 116.5(3) y O1 C16 C15 114.9(3) y 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 C3 . 1.747(4) y S1 C11 . 1.773(5) y S2 C4 . 1.764(3) y S2 C12 . 1.825(4) y N1 C2 . 1.312(5) y N1 C10 . 1.351(4) y N1 H1 . .91(5) y C2 C3 . 1.402(5) ? C2 H2 . .9300 ? C3 C4 . 1.387(5) ? C4 C5 . 1.413(5) ? C5 C6 . 1.407(5) ? C5 C10 . 1.419(4) ? C6 C7 . 1.349(5) ? C6 H6 . .9300 ? C7 C8 . 1.411(6) ? C7 H7 . .9300 ? C8 C9 . 1.359(5) ? C8 H8 . .9300 ? C9 C10 . 1.405(5) ? C9 H9 . .9300 ? C11 H11A . .9600 ? C11 H11B . .9600 ? C11 H11C . .9600 ? C12 C13 . 1.444(6) ? C12 H12A . .9700 ? C12 H12B . .9700 ? C13 C14 . 1.154(6) y C14 H14 . .9300 ? Cl1 C15 . 1.757(4) ? Cl2 C15 . 1.760(4) ? Cl3 C15 . 1.759(4) ? O1 C16 . 1.249(4) y O2 C16 . 1.219(4) y C15 C16 . 1.557(5) ? 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 _geom_torsion_publ_flag C10 N1 C2 C3 .2(5) ? N1 C2 C3 C4 2.7(5) ? N1 C2 C3 S1 -177.9(3) ? C11 S1 C3 C4 -169.0(4) ? C11 S1 C3 C2 11.7(4) y C2 C3 C4 C5 -3.7(5) ? S1 C3 C4 C5 177.0(2) ? C2 C3 C4 S2 178.7(3) ? S1 C3 C4 S2 -.6(4) y C12 S2 C4 C3 -75.1(3) y C12 S2 C4 C5 107.3(3) ? C3 C4 C5 C6 -177.8(3) ? S2 C4 C5 C6 -.2(5) ? C3 C4 C5 C10 1.8(5) ? S2 C4 C5 C10 179.4(2) ? C4 C5 C6 C7 178.5(3) ? C10 C5 C6 C7 -1.1(5) ? C5 C6 C7 C8 .7(6) ? C6 C7 C8 C9 .2(6) ? C7 C8 C9 C10 -.7(6) ? C2 N1 C10 C9 178.0(3) ? C2 N1 C10 C5 -2.2(5) ? C8 C9 C10 N1 -179.9(3) ? C8 C9 C10 C5 .3(5) ? C6 C5 C10 N1 -179.3(3) ? C4 C5 C10 N1 1.1(5) ? C6 C5 C10 C9 .6(5) ? C4 C5 C10 C9 -179.0(3) ? C4 S2 C12 C13 -63.8(4) y S2 C12 C13 C14 8E1(2) ? Cl1 C15 C16 O2 -92.3(3) ? Cl3 C15 C16 O2 147.8(3) ? Cl2 C15 C16 O2 26.6(4) ? Cl1 C15 C16 O1 86.0(3) y Cl3 C15 C16 O1 -33.8(4) ? Cl2 C15 C16 O1 -155.1(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21135589 2 PubChem 139057899