#------------------------------------------------------------------------------
#$Date: 2025-10-06 09:54:01 +0200 (Mon 06 de Oct de 2025) $
#$Revision: 302533 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/53/1575361.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_1575361
loop_
_publ_author_name
'Singh, Ashi'
'Avinash, Kiran'
'Pradhan, Amit Kumar'
'Prajapati, Aditya Kumar'
'Edwards, Alison J.'
'Thomas, Sajesh P.'
_publ_section_title
;
 Weak yet directional: supramolecular interactions of thiols unravelled by
 quantum crystallography.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              16016
_journal_page_last               16026
_journal_paper_doi               10.1039/d5sc04450b
_journal_volume                  16
_journal_year                    2025
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-06-03 deposited with the CCDC.	2025-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                95.908(3)
_cell_angle_beta                 103.030(3)
_cell_angle_gamma                102.643(3)
_cell_formula_units_Z            1
_cell_length_a                   5.0339(5)
_cell_length_b                   5.7865(5)
_cell_length_c                   6.4524(6)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    109(1)
_cell_measurement_theta_max      33.40
_cell_measurement_theta_min      3.28
_cell_volume                     176.36(3)
_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)'
_diffrn_ambient_temperature      109(1)
_diffrn_measured_fraction_theta_full 0.9953
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.9953
_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       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15075
_diffrn_reflns_point_group_measured_fraction_full 0.9850
_diffrn_reflns_point_group_measured_fraction_max 0.9908
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         33.41
_diffrn_reflns_theta_min         3.28
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1042 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.9294.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_description       block
_exptl_crystal_F_000             86
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.1443
_refine_diff_density_min         -0.1167
_refine_diff_density_rms         0.0399
_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   0.030(13)
_refine_ls_d_res_high            0.6454
_refine_ls_d_res_low             6.2051
_refine_ls_goodness_of_fit_ref   1.0267
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0267
_refine_ls_R_factor_all          0.0125
_refine_ls_R_factor_gt           0.0124
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0065P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0251
_refine_ls_wR_factor_ref         0.0251
_reflns_Friedel_coverage         0.984
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              9
_reflns_limit_l_min              -9
_reflns_number_gt                2697
_reflns_number_total             2705
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5sc04450b2.cif
_cod_data_source_block           NAC
_cod_depositor_comments
'Adding full bibliography for 1575356--1575368.cif.'
_cod_original_sg_symbol_Hall     ' P 1'
_cod_database_code               1575361
_olex2_refinement_description
;
;
_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 0.10341(2) 0.102167(16) 0.513061(15) 0.01248(3) Uani 1.000000 .
H1 H 0.141(2) 0.2391(19) 0.7036(17) 0.038(3) Uani 1.000000 .
O2 O 0.33608(7) 0.33315(6) 0.05427(5) 0.01878(7) Uani 1.000000 .
O1 O 0.89678(7) 0.60977(6) 0.82424(5) 0.01429(6) Uani 1.000000 .
O3 O 0.18437(7) 0.62581(6) 0.20837(5) 0.01413(6) Uani 1.000000 .
H3 H 0.071(3) 0.624(2) 0.0512(18) 0.029(3) Uani 1.000000 .
N1 N 0.50035(7) 0.64014(6) 0.59790(5) 0.01008(6) Uani 1.000000 .
H1A H 0.334(2) 0.7132(18) 0.5733(17) 0.034(2) Uani 1.000000 .
C1 C 0.66206(9) 0.89606(8) 0.94655(7) 0.01411(8) Uani 1.000000 .
H1B H 0.456(2) 0.9324(19) 0.9072(18) 0.046(3) Uani 1.000000 .
H1C H 0.822(2) 1.0589(15) 0.9535(17) 0.039(3) Uani 1.000000 .
H1D H 0.706(2) 0.8475(16) 1.1045(14) 0.034(2) Uani 1.000000 .
C2 C 0.69410(9) 0.70338(8) 0.78702(7) 0.01018(7) Uani 1.000000 .
C3 C 0.52244(8) 0.46203(7) 0.43105(6) 0.00947(7) Uani 1.000000 .
H3A H 0.7431(18) 0.5065(14) 0.4141(15) 0.023(2) Uani 1.000000 .
C4 C 0.33602(8) 0.46749(7) 0.21095(6) 0.01057(7) Uani 1.000000 .
C5 C 0.45785(8) 0.20752(7) 0.48534(7) 0.01084(7) Uani 1.000000 .
H5A H 0.6109(17) 0.1992(14) 0.6326(14) 0.0279(19) Uani 1.000000 .
H5B H 0.4771(17) 0.0851(14) 0.3541(14) 0.0285(19) 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
C5 S1 H1 96.7(5) . . ?
C4 O3 H3 110.3(7) . . ?
C2 N1 H1A 119.4(6) . . ?
C3 N1 H1A 119.8(6) . . ?
C3 N1 C2 120.82(4) . . ?
H1C C1 H1B 109.5(8) . . ?
H1D C1 H1B 110.0(8) . . ?
H1D C1 H1C 106.1(8) . . ?
C2 C1 H1B 113.2(6) . . ?
C2 C1 H1C 108.3(5) . . ?
C2 C1 H1D 109.5(5) . . ?
N1 C2 O1 120.66(4) . . ?
C1 C2 O1 121.96(4) . . ?
C1 C2 N1 117.35(4) . . ?
H3A C3 N1 108.3(4) . . ?
C4 C3 N1 112.33(3) . . ?
C4 C3 H3A 105.8(5) . . ?
C5 C3 N1 112.56(3) . . ?
C5 C3 H3A 107.8(4) . . ?
C5 C3 C4 109.68(3) . . ?
O3 C4 O2 124.72(4) . . ?
C3 C4 O2 120.19(4) . . ?
C3 C4 O3 115.09(3) . . ?
C3 C5 S1 113.94(3) . . ?
H5A C5 S1 110.1(4) . . ?
H5A C5 C3 109.3(4) . . ?
H5B C5 S1 106.0(4) . . ?
H5B C5 C3 108.4(5) . . ?
H5B C5 H5A 109.0(7) . . ?
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 1.344(10) . ?
S1 C5 1.8103(4) . ?
O2 C4 1.2103(5) . ?
O1 C2 1.2451(6) . ?
O3 H3 1.043(11) . ?
O3 C4 1.3137(5) . ?
N1 H1A 1.009(9) . ?
N1 C2 1.3377(6) . ?
N1 C3 1.4523(5) . ?
C1 H1B 1.085(10) . ?
C1 H1C 1.087(8) . ?
C1 H1D 1.073(9) . ?
C1 C2 1.4987(7) . ?
C3 H3A 1.117(8) . ?
C3 C4 1.5231(6) . ?
C3 C5 1.5315(6) . ?
C5 H5A 1.093(8) . ?
C5 H5B 1.083(8) . ?
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 C5 C3 N1 61.88(3) . . . . ?
S1 C5 C3 C4 -63.95(3) . . . . ?
O2 C4 C3 N1 178.33(4) . . . . ?
O2 C4 C3 C5 -55.70(4) . . . . ?
O1 C2 N1 C3 -0.36(5) . . . . ?
O3 C4 C3 N1 -1.26(4) . . . . ?
O3 C4 C3 C5 124.71(4) . . . . ?
