#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202146.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_2202146 loop_ _publ_author_name 'Deschamps, Jeffrey R.' 'Suwandi, Lita S.' 'Konaklieva, Monika' _publ_section_title ; 3,3-Bis(methylthio)-2-oxo-N-phenylpropanamide ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o308 _journal_page_last o309 _journal_paper_doi 10.1107/S1600536803002769 _journal_volume 59 _journal_year 2003 _chemical_formula_sum 'C12 H15 N O3 S2' _chemical_formula_weight 285.37 _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 99.0990(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 29.7331(5) _cell_length_b 5.34990(10) _cell_length_c 17.4428(3) _cell_measurement_reflns_used 2025 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 66.93 _cell_measurement_theta_min 8.43 _cell_volume 2739.70(8) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction ; SAINT (Bruker, 2000) and XPREP (Bruker, 1997) ; _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 2000)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.948 _diffrn_measured_fraction_theta_max 0.948 _diffrn_measurement_device 'Bruker SMART 6000 CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'Gobel optics' _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8381 _diffrn_reflns_reduction_process SAINT _diffrn_reflns_theta_full 67.10 _diffrn_reflns_theta_max 67.10 _diffrn_reflns_theta_min 5.14 _diffrn_standards_decay_% 'random variation of 0.7' _diffrn_standards_interval_time variable _diffrn_standards_number 108 _exptl_absorpt_coefficient_mu 3.537 _exptl_absorpt_correction_T_max 0.776 _exptl_absorpt_correction_T_min 0.527 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 1200 _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.239 _refine_diff_density_min -0.307 _refine_ls_extinction_coef 0.0037(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 168 _refine_ls_number_reflns 2328 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0438 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0810P)^2^+0.0191P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1152 _refine_ls_wR_factor_ref 0.1196 _reflns_number_gt 1977 _reflns_number_total 2328 _reflns_threshold_expression I>2\s(I) _cod_data_source_file om6129.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 2739.70(10) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2202146 _cod_database_fobs_code 2202146 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 1.00825(2) 0.21600(10) 0.63803(3) 0.0575(2) Uani d . 1 . . S C1A 1.02491(8) 0.5234(4) 0.61350(14) 0.0710(6) Uani d . 1 . . C H1AA 1.0562 0.5215 0.6061 0.106 Uiso calc R 1 . . H H1AB 1.0213 0.6367 0.6548 0.106 Uiso calc R 1 . . H H1AC 1.0061 0.5770 0.5665 0.106 Uiso calc R 1 . . H S2 0.90875(2) 0.28954(11) 0.55865(3) 0.0700(2) Uani d . 1 . . S C2A 0.91947(8) 0.0014(5) 0.51307(12) 0.0744(6) Uani d . 1 . . C H2AA 0.8994 -0.0131 0.4644 0.112 Uiso calc R 1 . . H H2AB 0.9143 -0.1355 0.5462 0.112 Uiso calc R 1 . . H H2AC 0.9505 -0.0022 0.5041 0.112 Uiso calc R 1 . . H N1 0.87084(6) -0.0359(3) 0.76384(9) 0.0494(4) Uani d . 1 . . N H1 0.8806(8) -0.171(4) 0.7569(12) 0.059 Uiso d . 1 . . H C1' 0.83335(6) -0.0167(3) 0.80527(9) 0.0456(4) Uani d . 1 . . C C2' 0.80185(7) 0.1726(4) 0.79172(11) 0.0545(5) Uani d . 1 . . C H2'A 0.8050 0.2935 0.7547 0.065 Uiso calc R 1 . . H C3' 0.76566(7) 0.1862(4) 0.83212(11) 0.0558(5) Uani d . 1 . . C H3'A 0.7445 0.3148 0.8221 0.067 Uiso calc R 1 . . H C4' 0.76094(6) 0.0066(4) 0.88790(10) 0.0541(5) Uani d . 1 . . C O4' 0.72688(5) 0.0047(3) 0.93192(8) 0.0743(5) Uani d . 1 . . O C4'A 0.69421(8) 0.2021(5) 0.92141(15) 0.0797(7) Uani d . 1 . . C H4'A 0.6780 0.1979 0.8692 0.120 Uiso calc R 1 . . H H4'B 0.7095 0.3597 0.9307 0.120 Uiso calc R 1 . . H H4'C 0.6731 0.1814 0.9572 0.120 Uiso calc R 1 . . H C5' 0.79211(7) -0.1880(4) 0.90041(11) 0.0592(5) Uani d . 1 . . C H5'A 0.7888 -0.3109 0.9368 0.071 Uiso calc R 1 . . H C6' 0.82774(7) -0.2000(4) 0.85946(10) 0.0536(5) Uani d . 1 . . C H6'A 0.8483 -0.3318 0.8680 0.064 Uiso calc R 1 . . H C2 0.89239(6) 0.1586(4) 0.73687(10) 0.0496(5) Uani d . 1 . . C O2 0.88393(5) 0.3790(3) 0.74467(9) 0.0650(4) Uani d . 1 . . O C3 0.93126(6) 0.0747(3) 0.69416(10) 0.0493(4) Uani d . 1 . . C O3 0.94307(5) -0.1415(3) 0.69422(8) 0.0610(4) Uani d . 1 . . O C4 0.95009(7) 0.2770(3) 0.64857(11) 0.0527(5) Uani d . 1 . . C H4A 0.9489 0.4357 0.6762 0.063 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 0.0640(4) 0.0403(4) 0.0752(3) 0.0001(2) 0.0326(2) 0.0014(2) C1A 0.0762(14) 0.0562(15) 0.0873(13) -0.0115(11) 0.0337(11) 0.0084(11) S2 0.0792(4) 0.0551(4) 0.0803(4) 0.0185(3) 0.0267(3) 0.0137(3) C2A 0.0849(16) 0.0679(17) 0.0712(11) 0.0025(12) 0.0149(11) -0.0049(11) N1 0.0593(9) 0.0341(10) 0.0600(7) -0.0033(7) 0.0257(7) -0.0017(7) C1' 0.0498(10) 0.0387(11) 0.0501(7) -0.0058(7) 0.0137(7) 0.0001(7) C2' 0.0576(11) 0.0468(13) 0.0615(9) -0.0022(9) 0.0167(8) 0.0108(9) C3' 0.0494(10) 0.0490(13) 0.0708(10) 0.0023(8) 0.0151(8) 0.0108(9) C4' 0.0486(10) 0.0556(13) 0.0609(9) -0.0058(9) 0.0173(8) 0.0047(9) O4' 0.0620(9) 0.0831(12) 0.0864(9) 0.0083(8) 0.0381(7) 0.0203(8) C4'A 0.0560(13) 0.091(2) 0.0976(16) 0.0083(11) 0.0293(12) 0.0109(14) C5' 0.0624(12) 0.0534(14) 0.0658(10) -0.0004(9) 0.0226(9) 0.0176(9) C6' 0.0582(11) 0.0422(12) 0.0629(10) 0.0014(8) 0.0178(8) 0.0088(8) C2 0.0598(11) 0.0348(11) 0.0585(9) -0.0057(8) 0.0222(8) -0.0022(8) O2 0.0755(9) 0.0329(8) 0.0976(9) -0.0031(7) 0.0472(8) -0.0080(7) C3 0.0618(11) 0.0310(11) 0.0605(9) -0.0017(8) 0.0265(8) -0.0012(8) O3 0.0839(10) 0.0293(8) 0.0784(8) 0.0009(7) 0.0389(7) 0.0002(7) C4 0.0686(13) 0.0283(11) 0.0691(11) -0.0003(8) 0.0354(10) 0.0004(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 C1A S1 C4 99.48(10) S1 C1A H1AA 109.5 S1 C1A H1AB 109.5 H1AA C1A H1AB 109.5 S1 C1A H1AC 109.5 H1AA C1A H1AC 109.5 H1AB C1A H1AC 109.5 C2A S2 C4 101.91(9) S2 C2A H2AA 109.5 S2 C2A H2AB 109.5 H2AA C2A H2AB 109.5 S2 C2A H2AC 109.5 H2AA C2A H2AC 109.5 H2AB C2A H2AC 109.5 C2 N1 C1' 125.15(17) C2 N1 H1 116.3(17) C1' N1 H1 118.5(17) C2' C1' C6' 119.01(17) C2' C1' N1 122.18(16) C6' C1' N1 118.78(17) C1' C2' C3' 121.15(17) C1' C2' H2'A 119.4 C3' C2' H2'A 119.4 C2' C3' C4' 119.64(19) C2' C3' H3'A 120.2 C4' C3' H3'A 120.2 O4' C4' C5' 116.27(17) O4' C4' C3' 124.40(19) C5' C4' C3' 119.32(18) C4' O4' C4'A 118.24(17) O4' C4'A H4'A 109.5 O4' C4'A H4'B 109.5 H4'A C4'A H4'B 109.5 O4' C4'A H4'C 109.5 H4'A C4'A H4'C 109.5 H4'B C4'A H4'C 109.5 C6' C5' C4' 120.38(17) C6' C5' H5'A 119.8 C4' C5' H5'A 119.8 C5' C6' C1' 120.47(19) C5' C6' H6'A 119.8 C1' C6' H6'A 119.8 O2 C2 N1 126.26(17) O2 C2 C3 121.41(16) N1 C2 C3 112.32(16) O3 C3 C4 123.86(16) O3 C3 C2 121.29(16) C4 C3 C2 114.68(15) C3 C4 S1 111.61(13) C3 C4 S2 102.90(13) S1 C4 S2 116.40(10) C3 C4 H4A 108.5 S1 C4 H4A 108.5 S2 C4 H4A 108.5 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 C1A . 1.789(2) ? S1 C4 . 1.797(2) ? C1A H1AA . 0.9600 ? C1A H1AB . 0.9600 ? C1A H1AC . 0.9600 ? S2 C2A . 1.786(2) ? S2 C4 . 1.835(2) ? C2A H2AA . 0.9600 ? C2A H2AB . 0.9600 ? C2A H2AC . 0.9600 ? N1 C2 . 1.345(2) ? N1 C1' . 1.425(2) ? N1 H1 . 0.80(2) ? C1' C2' . 1.374(3) ? C1' C6' . 1.391(2) ? C2' C3' . 1.378(3) ? C2' H2'A . 0.9300 ? C3' C4' . 1.390(3) ? C3' H3'A . 0.9300 ? C4' O4' . 1.364(2) ? C4' C5' . 1.388(3) ? O4' C4'A . 1.427(3) ? C4'A H4'A . 0.9600 ? C4'A H4'B . 0.9600 ? C4'A H4'C . 0.9600 ? C5' C6' . 1.370(3) ? C5' H5'A . 0.9300 ? C6' H6'A . 0.9300 ? C2 O2 . 1.218(2) ? C2 C3 . 1.538(2) ? C3 O3 . 1.209(2) ? C3 C4 . 1.503(2) ? C4 H4A . 0.9800 ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21131900 2 PubChem 86213972