#------------------------------------------------------------------------------ #$Date: 2024-12-25 03:51:10 +0200 (Wed, 25 Dec 2024) $ #$Revision: 296964 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/35/1573534.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1573534 _journal_paper_doi 10.1039/D4RA07780F _chemical_absolute_configuration syn _chemical_formula_moiety 'C7 H9 N O S3' _chemical_formula_sum 'C7 H9 N O S3' _chemical_formula_weight 219.33 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2024-09-27 deposited with the CCDC. 2024-12-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.2493(7) _cell_length_b 12.0624(18) _cell_length_c 14.1479(16) _cell_measurement_reflns_used 9466 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.59 _cell_measurement_theta_min 2.878 _cell_volume 895.8(2) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_unetI/netI 0.0197 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 29567 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.601 _diffrn_reflns_theta_min 2.880 _exptl_absorpt_coefficient_mu 0.774 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_correction_T_min 0.814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.626 _exptl_crystal_description paralellepiped _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.380 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.359 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.073 _refine_ls_abs_structure_details ; Flack x determined using 676 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.253 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1863 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.253 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0381 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0113P)^2^+1.1511P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.0873 _reflns_Friedel_coverage 0.669 _reflns_Friedel_fraction_full 0.998 _reflns_Friedel_fraction_max 0.987 _reflns_number_gt 1775 _reflns_number_total 1863 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ra07780f2.cif _cod_data_source_block Compound_1c _cod_database_code 1573534 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.757 _shelx_estimated_absorpt_t_max 0.941 _shelx_res_file ; TITL mo_ValerieC_VC269_1829_0m_a.res in P2(1)2(1)2(1) mo_ValerieC_VC269_1829_0m_a.res created by SHELXL-2018/3 at 18:40:35 on 14-Feb-2024 REM Old TITL mo_ValerieC_VC269_1829_0m in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.150, Rweak 0.047, Alpha 0.002, Orientation as input REM Flack x = 0.082 ( 0.083 ) from Parsons' quotients REM Formula found by SHELXT: C7 N O S3 CELL 0.71073 5.2493 12.0624 14.1479 90.000 90.000 90.000 ZERR 4.000 0.0007 0.0018 0.0016 0.000 0.000 0.000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H N O S UNIT 28 36 4 4 12 TEMP -273.150 L.S. 10 BOND $H CONF ACTA TEMP 25 OMIT -1 1 17 OMIT 1 1 17 OMIT 1 3 17 OMIT -1 5 16 SIZE 0.38 0.09 0.08 LIST 4 FMAP 2 PLAN 5 HTAB WGHT 0.011300 1.151100 FVAR 0.23106 S10 5 0.220168 0.670806 0.704658 11.00000 0.03084 0.03627 = 0.07454 -0.01290 0.00718 0.00846 N1 3 0.601493 0.488966 0.627900 11.00000 0.02265 0.02691 = 0.02338 -0.00086 -0.00379 0.00253 O1 4 0.158803 0.671176 0.523169 11.00000 0.03502 0.04957 = 0.08293 0.02423 -0.02173 0.00168 C9 1 0.300747 0.644646 0.585710 11.00000 0.02335 0.02209 = 0.06067 0.00845 -0.00653 -0.00409 C8 1 0.561571 0.590570 0.571439 11.00000 0.02327 0.02834 = 0.03216 0.00458 -0.00498 -0.00458 AFIX 13 H8 2 0.692595 0.644489 0.589369 11.00000 -1.20000 AFIX 0 S6 5 0.485745 0.417595 0.457742 11.00000 0.08050 0.05403 = 0.03128 -0.01400 -0.00221 -0.00915 C7 1 0.607978 0.556957 0.470513 11.00000 0.04090 0.05403 = 0.03460 0.00343 -0.00190 -0.01090 AFIX 23 H7A 2 0.788727 0.558841 0.456350 11.00000 -1.20000 H7B 2 0.520618 0.606983 0.427724 11.00000 -1.20000 AFIX 0 S3 5 0.263623 0.398723 0.749304 11.00000 0.04611 0.03791 = 0.04484 0.00462 0.01387 -0.00451 C5 1 0.484132 0.391943 0.583815 11.00000 0.03738 0.02626 = 0.03238 -0.00519 0.00184 0.00470 AFIX 13 H5 2 0.588003 0.326337 0.597380 11.00000 -1.20000 AFIX 0 C4 1 0.217753 0.375346 0.625103 11.00000 0.03629 0.03007 = 0.04841 -0.00308 -0.00323 -0.00835 AFIX 23 H4A 2 0.156180 0.300821 0.613210 11.00000 -1.20000 H4B 2 0.097982 0.428204 0.598741 11.00000 -1.20000 AFIX 0 C2 1 0.540066 0.492502 0.728205 11.00000 0.02426 0.03796 = 0.02897 0.00162 -0.00127 0.00440 AFIX 13 H2 2 0.686244 0.463030 0.763207 11.00000 -1.20000 AFIX 0 C11 1 0.491116 0.608994 0.762541 11.00000 0.03283 0.04463 = 0.03765 -0.01320 0.00073 -0.00188 AFIX 23 H11A 2 0.640792 0.654101 0.750810 11.00000 -1.20000 H11B 2 0.461612 0.607646 0.830213 11.00000 -1.20000 REM ##### AFIX 0 HKLF 4 REM mo_ValerieC_VC269_1829_0m_a.res in P2(1)2(1)2(1) REM wR2 = 0.0873, GooF = S = 1.253, Restrained GooF = 1.253 for all data REM R1 = 0.0381 for 1775 Fo > 4sig(Fo) and 0.0405 for all 1863 data REM 109 parameters refined using 0 restraints END WGHT 0.0113 1.1511 REM Instructions for potential hydrogen bonds EQIV $1 x+1, y, z HTAB C8 O1_$1 HTAB C7 O1_$1 EQIV $2 -x+1/2, -y+1, z-1/2 HTAB C7 S3_$2 EQIV $3 x-1/2, -y+1/2, -z+1 HTAB C4 S6_$3 EQIV $4 -x+1, y+1/2, -z+3/2 HTAB C11 S3_$4 EQIV $5 -x+1/2, -y+1, z+1/2 HTAB C11 S6_$5 REM Highest difference peak 0.359, deepest hole -0.273, 1-sigma level 0.073 Q1 1 0.2275 0.3950 0.6836 11.00000 0.05 0.36 Q2 1 0.4616 0.3988 0.4021 11.00000 0.05 0.32 Q3 1 0.5146 0.3983 0.5255 11.00000 0.05 0.30 Q4 1 0.2017 0.6514 0.6450 11.00000 0.05 0.26 Q5 1 0.5102 0.5566 0.7403 11.00000 0.05 0.25 ; _shelx_res_checksum 24126 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S10 S 0.2202(2) 0.67081(10) 0.70466(11) 0.0472(3) Uani 1 1 d . . . . . N1 N 0.6015(6) 0.4890(3) 0.6279(2) 0.0243(7) Uani 1 1 d . . . . . O1 O 0.1588(6) 0.6712(3) 0.5232(3) 0.0558(11) Uani 1 1 d . . . . . C9 C 0.3007(8) 0.6446(3) 0.5857(4) 0.0354(11) Uani 1 1 d . . . . . C8 C 0.5616(8) 0.5906(3) 0.5714(3) 0.0279(9) Uani 1 1 d . . . . . H8 H 0.692595 0.644489 0.589369 0.034 Uiso 1 1 calc R U . . . S6 S 0.4857(3) 0.41760(12) 0.45774(9) 0.0553(4) Uani 1 1 d . . . . . C7 C 0.6080(10) 0.5570(4) 0.4705(3) 0.0432(12) Uani 1 1 d . . . . . H7A H 0.788727 0.558841 0.456350 0.052 Uiso 1 1 calc R U . . . H7B H 0.520618 0.606983 0.427724 0.052 Uiso 1 1 calc R U . . . S3 S 0.2636(3) 0.39872(10) 0.74930(9) 0.0430(3) Uani 1 1 d . . . . . C5 C 0.4841(9) 0.3919(3) 0.5838(3) 0.0320(9) Uani 1 1 d . . . . . H5 H 0.588003 0.326337 0.597380 0.038 Uiso 1 1 calc R U . . . C4 C 0.2178(10) 0.3753(4) 0.6251(3) 0.0383(11) Uani 1 1 d . . . . . H4A H 0.156180 0.300821 0.613210 0.046 Uiso 1 1 calc R U . . . H4B H 0.097982 0.428204 0.598741 0.046 Uiso 1 1 calc R U . . . C2 C 0.5401(8) 0.4925(3) 0.7282(3) 0.0304(9) Uani 1 1 d . . . . . H2 H 0.686244 0.463030 0.763207 0.036 Uiso 1 1 calc R U . . . C11 C 0.4911(9) 0.6090(4) 0.7625(3) 0.0384(10) Uani 1 1 d . . . . . H11A H 0.640792 0.654101 0.750810 0.046 Uiso 1 1 calc R U . . . H11B H 0.461612 0.607646 0.830213 0.046 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S10 0.0308(6) 0.0363(6) 0.0745(9) -0.0129(6) 0.0072(6) 0.0085(5) N1 0.0226(17) 0.0269(17) 0.0234(17) -0.0009(13) -0.0038(13) 0.0025(14) O1 0.0350(18) 0.050(2) 0.083(3) 0.024(2) -0.0217(19) 0.0017(18) C9 0.023(2) 0.0221(19) 0.061(3) 0.0084(19) -0.007(2) -0.0041(17) C8 0.023(2) 0.028(2) 0.032(2) 0.0046(17) -0.0050(16) -0.0046(18) S6 0.0805(10) 0.0540(8) 0.0313(6) -0.0140(6) -0.0022(7) -0.0091(8) C7 0.041(3) 0.054(3) 0.035(3) 0.003(2) -0.002(2) -0.011(2) S3 0.0461(7) 0.0379(6) 0.0448(6) 0.0046(5) 0.0139(6) -0.0045(6) C5 0.037(2) 0.026(2) 0.032(2) -0.0052(17) 0.002(2) 0.005(2) C4 0.036(2) 0.030(2) 0.048(3) -0.0031(19) -0.003(2) -0.008(2) C2 0.0243(19) 0.038(2) 0.029(2) 0.0016(17) -0.0013(17) 0.0044(18) C11 0.033(2) 0.045(2) 0.038(2) -0.013(2) 0.001(2) -0.002(2) 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' N N 0.0061 0.0033 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 S10 C11 99.8(2) . . ? C2 N1 C5 110.2(3) . . ? C2 N1 C8 118.1(3) . . ? C5 N1 C8 111.9(3) . . ? O1 C9 C8 124.9(5) . . ? O1 C9 S10 120.5(4) . . ? C8 C9 S10 114.6(3) . . ? N1 C8 C7 105.5(4) . . ? N1 C8 C9 114.2(3) . . ? C7 C8 C9 112.7(4) . . ? N1 C8 H8 108.1 . . ? C7 C8 H8 108.1 . . ? C9 C8 H8 108.1 . . ? C7 S6 C5 93.6(2) . . ? C8 C7 S6 106.7(3) . . ? C8 C7 H7A 110.4 . . ? S6 C7 H7A 110.4 . . ? C8 C7 H7B 110.4 . . ? S6 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? C4 S3 C2 92.5(2) . . ? N1 C5 C4 109.1(3) . . ? N1 C5 S6 106.3(3) . . ? C4 C5 S6 113.8(3) . . ? N1 C5 H5 109.2 . . ? C4 C5 H5 109.2 . . ? S6 C5 H5 109.2 . . ? C5 C4 S3 103.3(3) . . ? C5 C4 H4A 111.1 . . ? S3 C4 H4A 111.1 . . ? C5 C4 H4B 111.1 . . ? S3 C4 H4B 111.1 . . ? H4A C4 H4B 109.1 . . ? N1 C2 C11 112.3(3) . . ? N1 C2 S3 108.1(3) . . ? C11 C2 S3 112.4(3) . . ? N1 C2 H2 108.0 . . ? C11 C2 H2 108.0 . . ? S3 C2 H2 108.0 . . ? C2 C11 S10 111.9(3) . . ? C2 C11 H11A 109.2 . . ? S10 C11 H11A 109.2 . . ? C2 C11 H11B 109.2 . . ? S10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S10 C9 1.764(5) . ? S10 C11 1.803(5) . ? N1 C2 1.456(5) . ? N1 C5 1.462(5) . ? N1 C8 1.478(5) . ? O1 C9 1.200(5) . ? C9 C8 1.530(6) . ? C8 C7 1.504(6) . ? C8 H8 0.9800 . ? S6 C7 1.808(5) . ? S6 C5 1.810(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? S3 C4 1.796(5) . ? S3 C2 1.864(5) . ? C5 C4 1.529(7) . ? C5 H5 0.9800 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C2 C11 1.509(6) . ? C2 H2 0.9800 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 S10 C9 O1 177.7(4) . . . . ? C11 S10 C9 C8 -4.1(3) . . . . ? C2 N1 C8 C7 -172.8(3) . . . . ? C5 N1 C8 C7 -43.2(5) . . . . ? C2 N1 C8 C9 -48.6(5) . . . . ? C5 N1 C8 C9 81.0(4) . . . . ? O1 C9 C8 N1 -129.3(4) . . . . ? S10 C9 C8 N1 52.6(4) . . . . ? O1 C9 C8 C7 -9.0(6) . . . . ? S10 C9 C8 C7 172.8(3) . . . . ? N1 C8 C7 S6 36.4(4) . . . . ? C9 C8 C7 S6 -88.8(4) . . . . ? C5 S6 C7 C8 -18.2(4) . . . . ? C2 N1 C5 C4 39.5(5) . . . . ? C8 N1 C5 C4 -94.1(4) . . . . ? C2 N1 C5 S6 162.6(3) . . . . ? C8 N1 C5 S6 29.0(4) . . . . ? C7 S6 C5 N1 -5.3(3) . . . . ? C7 S6 C5 C4 114.8(3) . . . . ? N1 C5 C4 S3 -42.8(4) . . . . ? S6 C5 C4 S3 -161.3(2) . . . . ? C2 S3 C4 C5 27.4(3) . . . . ? C5 N1 C2 C11 -141.5(4) . . . . ? C8 N1 C2 C11 -11.1(5) . . . . ? C5 N1 C2 S3 -17.0(4) . . . . ? C8 N1 C2 S3 113.4(3) . . . . ? C4 S3 C2 N1 -7.3(3) . . . . ? C4 S3 C2 C11 117.2(3) . . . . ? N1 C2 C11 S10 62.4(4) . . . . ? S3 C2 C11 S10 -59.7(4) . . . . ? C9 S10 C11 C2 -50.8(4) . . . . ?