#------------------------------------------------------------------------------
#$Date: 2025-08-12 01:13:26 +0300 (Tue, 12 Aug 2025) $
#$Revision: 301705 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/53/1575358.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_1575358
_journal_paper_doi               10.1039/D5SC04450B
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C5 H9 N O3 S'
_chemical_formula_sum            'C5 H9 N O3 S'
_chemical_formula_weight         163.198
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_Int_Tables_number      1
_audit_creation_date             2025-01-09
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-03 deposited with the CCDC.	2025-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                96.464(1)
_cell_angle_beta                 103.867(1)
_cell_angle_gamma                102.090(1)
_cell_formula_units_Z            1
_cell_length_a                   5.0877(2)
_cell_length_b                   5.8827(2)
_cell_length_c                   6.5179(2)
_cell_measurement_reflns_used    11013
_cell_measurement_temperature    288(1)
_cell_measurement_theta_max      33.20
_cell_measurement_theta_min      3.60
_cell_volume                     182.448(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      288(1)
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9978
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.9954
_diffrn_reflns_Laue_measured_fraction_max 0.9978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11013
_diffrn_reflns_point_group_measured_fraction_full 0.9885
_diffrn_reflns_point_group_measured_fraction_max 0.9925
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         33.22
_diffrn_reflns_theta_min         3.27
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7117
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0656 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.9534.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colorless'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       block
_exptl_crystal_F_000             86.0
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.187
_refine_diff_density_max         0.1456
_refine_diff_density_min         -0.1418
_refine_diff_density_rms         0.0382
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_d_res_high            0.6487
_refine_ls_d_res_low             6.2342
_refine_ls_goodness_of_fit_ref   1.1446
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2765
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.1446
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0209
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0081P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0402
_refine_ls_wR_factor_ref         0.0411
_reflns_Friedel_coverage         0.987
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              10
_reflns_limit_l_min              -10
_reflns_number_gt                2666
_reflns_number_total             2765
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5sc04450b2.cif
_cod_data_source_block           NAC_RT
_cod_original_sg_symbol_Hall     ' P 1'
_cod_database_code               1575358
_olex2_refinement_description
;
This dataset was used to perfrom X-ray quantum crystallographic technique of
Hirshfeld Atom Refinment (HAR) using NoSpherA2 module in Olex2 at B3LYP/def2TZVP
within a cluster of 8 angstrom.
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,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_refinement_flags_posn
S1 S 0.10741(4) 0.10721(3) 0.51192(3) 0.03719(6) Uani 1.000000 .
H1 H 0.142(4) 0.245(3) 0.703(3) 0.081(6) Uani 1.000000 .
O2 O 0.18513(13) 0.62036(11) 0.20854(8) 0.04123(15) Uani 1.000000 .
H2 H 0.069(4) 0.614(4) 0.058(2) 0.067(6) Uani 1.000000 .
O3 O 0.89428(13) 0.60985(12) 0.82424(9) 0.04200(15) Uani 1.000000 .
N1 N 0.49963(12) 0.63661(10) 0.59719(9) 0.02780(12) Uani 1.000000 .
H1A H 0.337(3) 0.713(3) 0.574(3) 0.068(5) Uani 1.000000 .
O1 O 0.33178(17) 0.33154(12) 0.05720(10) 0.0558(2) Uani 1.000000 .
C4 C 0.69336(16) 0.70153(14) 0.78585(11) 0.02889(13) Uani 1.000000 .
C3 C 0.51883(14) 0.45880(12) 0.43195(10) 0.02584(12) Uani 1.000000 .
H3 H 0.736(3) 0.496(2) 0.417(2) 0.049(3) Uani 1.000000 .
C2 C 0.33337(15) 0.46422(12) 0.21241(10) 0.02984(14) Uani 1.000000 .
C1 C 0.45511(14) 0.20973(13) 0.48457(12) 0.03003(13) Uani 1.000000 .
H1C H 0.608(3) 0.199(2) 0.633(3) 0.065(4) Uani 1.000000 .
H1B H 0.475(3) 0.087(2) 0.357(2) 0.064(4) Uani 1.000000 .
C5 C 0.6601(2) 0.89108(16) 0.94335(13) 0.04055(18) Uani 1.000000 .
H5A H 0.710(4) 0.851(3) 1.097(2) 0.086(6) Uani 1.000000 .
H5B H 0.468(5) 0.930(4) 0.909(3) 0.109(7) Uani 1.000000 .
H5C H 0.814(4) 1.048(3) 0.950(3) 0.099(7) Uani 1.000000 .
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
C1 S1 H1 97.8(8) . . ?
C2 O2 H2 110.8(13) . . ?
C4 N1 H1A 117.9(8) . . ?
C3 N1 H1A 121.0(8) . . ?
C3 N1 C4 121.16(6) . . ?
N1 C4 O3 120.57(8) . . ?
C5 C4 O3 122.17(7) . . ?
C5 C4 N1 117.25(7) . . ?
H3 C3 N1 109.1(7) . . ?
C2 C3 N1 112.20(6) . . ?
C2 C3 H3 106.1(7) . . ?
C1 C3 N1 112.87(6) . . ?
C1 C3 H3 106.4(7) . . ?
C1 C3 C2 109.85(6) . . ?
O1 C2 O2 124.45(7) . . ?
C3 C2 O2 115.29(6) . . ?
C3 C2 O1 120.26(7) . . ?
C3 C1 S1 114.57(5) . . ?
H1C C1 S1 109.0(8) . . ?
H1C C1 C3 110.0(7) . . ?
H1B C1 S1 106.5(8) . . ?
H1B C1 C3 108.9(8) . . ?
H1B C1 H1C 107.6(12) . . ?
H5A C5 C4 110.1(8) . . ?
H5B C5 C4 115.5(11) . . ?
H5B C5 H5A 110.3(18) . . ?
H5C C5 C4 107.9(10) . . ?
H5C C5 H5A 104.4(15) . . ?
H5C C5 H5B 107.9(18) . . ?
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
S1 H1 1.359(17) . ?
S1 C1 1.8037(7) . ?
O2 H2 1.010(13) . ?
O2 C2 1.3037(10) . ?
O3 C4 1.2398(11) . ?
N1 H1A 1.011(13) . ?
N1 C4 1.3361(9) . ?
N1 C3 1.4503(9) . ?
O1 C2 1.2035(10) . ?
C4 C5 1.4934(12) . ?
C3 H3 1.110(13) . ?
C3 C2 1.5213(9) . ?
C3 C1 1.5287(10) . ?
C1 H1C 1.100(13) . ?
C1 H1B 1.078(12) . ?
C5 H5A 1.036(14) . ?
C5 H5B 1.03(2) . ?
C5 H5C 1.064(15) . ?
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
S1 C1 C3 N1 61.54(5) . . . . ?
S1 C1 C3 C2 -64.49(6) . . . . ?
O2 C2 C3 N1 -1.51(7) . . . . ?
O2 C2 C3 C1 124.89(7) . . . . ?
O3 C4 N1 C3 -0.31(10) . . . . ?
N1 C3 C2 O1 177.96(7) . . . . ?
O1 C2 C3 C1 -55.63(9) . . . . ?
