#------------------------------------------------------------------------------
#$Date: 2025-10-06 09:54:01 +0200 (Mon 06 de Oct de 2025) $
#$Revision: 302533 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/53/1575357.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_1575357
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 rm
_chemical_formula_moiety         'C9 H15 N O3 S'
_chemical_formula_sum            'C9 H15 N O3 S'
_chemical_formula_weight         217.29
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     geom
_audit_update_record
;
2025-06-17 deposited with the CCDC.	2025-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7946(3)
_cell_length_b                   8.7946(5)
_cell_length_c                   17.4457(9)
_cell_measurement_reflns_used    97153
_cell_measurement_temperature    108
_cell_measurement_theta_max      2.33
_cell_measurement_theta_min      55.83
_cell_volume                     1042.48(9)
_computing_cell_refinement       'LaueG (Piltz, 2018b)'
_computing_data_collection       'Gumtree control system (ANSTO)'
_computing_data_reduction
;
argonne_boxes (Wilkinson et al., 1988) & LaueG (Piltz, 2018b)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'known from Xray'
_diffrn_ambient_temperature      108
_diffrn_measured_fraction_theta_full 0.873
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details      '20 images, exposure time 333 minutes'
_diffrn_measurement_device
;
Laue image-plate diffractometer KOALA2
;
_diffrn_measurement_method       Laue
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.85
_diffrn_reflns_av_R_equivalents  0.1108
_diffrn_reflns_av_unetI/netI     0.1279
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            52762
_diffrn_reflns_reduction_process 'LaueG (Piltz, 2018a)'
_diffrn_reflns_resolution_max    1.82
_diffrn_reflns_theta_full        89.90
_diffrn_reflns_theta_max         90.00
_diffrn_reflns_theta_min         3.935
_diffrn_source                   'nuclear reactor'
_diffrn_source_details           'thermal neutrons, supermirror guides'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  0.00
_exptl_absorpt_correction_T_min  0.00
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             132
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         1.10
_refine_diff_density_min         -1.13
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.2196
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.0002156
_refine_ls_shift/su_mean         0.0000454
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0212
_refine_ls_wR_factor_gt          0.0214
_refine_ls_wR_factor_ref         0.0212
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                2090
_reflns_number_total             2862
_reflns_threshold_expression     >2sigma(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0449
_oxford_refine_ls_scale          0.7336(8)
_oxford_reflns_number_all        2861
_cod_data_source_file            d5sc04450b2.cif
_cod_data_source_block           AS_CAP_neut
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1575356--1575368.cif.
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1575357
_oxford_refine_reflns_threshold_expression I>3.0\s(I)
_oxford_refine_ls_r_factor_all   0.0798
_oxford_refine_ls_wr_factor_all  0.0257
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.7455(3) 0.6402(2) 0.39346(11) 0.0224 1.0000 Uani . . . . . .
O1 O -0.13365(15) 0.25235(13) 0.40018(6) 0.0223 1.0000 Uani . . . . . .
O2 O 0.16764(16) 0.41830(12) 0.29821(6) 0.0196 1.0000 Uani . . . . . .
O3 O -0.24396(16) 0.13491(12) 0.29715(6) 0.0223 1.0000 Uani . . . . . .
N1 N 0.25632(9) 0.20868(7) 0.36201(3) 0.0132 1.0000 Uani . . . . . .
C1 C 0.10531(12) 0.11960(10) 0.32296(4) 0.0133 1.0000 Uani . . . . . .
C2 C 0.13685(13) -0.04408(10) 0.35271(6) 0.0188 1.0000 Uani . . . . . .
C3 C 0.34717(14) -0.04352(11) 0.38303(5) 0.0185 1.0000 Uani . . . . . .
C4 C 0.37036(13) 0.11592(9) 0.41636(5) 0.0158 1.0000 Uani . . . . . .
C5 C 0.27417(11) 0.35690(9) 0.34821(5) 0.0132 1.0000 Uani . . . . . .
C6 C 0.41663(12) 0.45029(10) 0.39590(5) 0.0142 1.0000 Uani . . . . . .
C7 C 0.54735(13) 0.54532(12) 0.34315(5) 0.0187 1.0000 Uani . . . . . .
C8 C -0.10018(11) 0.17666(10) 0.34367(5) 0.0148 1.0000 Uani . . . . . .
C9 C 0.29587(13) 0.54786(13) 0.45092(5) 0.0223 1.0000 Uani . . . . . .
H1 H 0.8564(4) 0.5170(3) 0.40254(19) 0.0520 1.0000 Uani . . . . . .
H3 H -0.2040(3) 0.0581(2) 0.25690(11) 0.0303 1.0000 Uani . . . . . .
H11 H 0.1244(3) 0.1293(2) 0.26026(10) 0.0273 1.0000 Uani . . . . . .
H21 H 0.1083(4) -0.1276(3) 0.30792(15) 0.0425 1.0000 Uani . . . . . .
H22 H 0.0348(3) -0.0687(3) 0.39917(15) 0.0424 1.0000 Uani . . . . . .
H31 H 0.4547(3) -0.0591(3) 0.33632(13) 0.0357 1.0000 Uani . . . . . .
H32 H 0.3735(4) -0.1319(3) 0.42591(14) 0.0390 1.0000 Uani . . . . . .
H41 H 0.5227(3) 0.1540(2) 0.41803(14) 0.0333 1.0000 Uani . . . . . .
H42 H 0.3063(3) 0.1244(3) 0.47343(11) 0.0361 1.0000 Uani . . . . . .
H61 H 0.5117(3) 0.3759(3) 0.42892(13) 0.0316 1.0000 Uani . . . . . .
H71 H 0.4637(4) 0.6355(3) 0.31530(14) 0.0406 1.0000 Uani . . . . . .
H72 H 0.6128(4) 0.4744(3) 0.29866(14) 0.0475 1.0000 Uani . . . . . .
H91 H 0.3930(4) 0.6194(3) 0.48503(13) 0.0426 1.0000 Uani . . . . . .
H92 H 0.1948(4) 0.6205(3) 0.41924(16) 0.0452 1.0000 Uani . . . . . .
H93 H 0.2100(5) 0.4763(4) 0.48943(17) 0.0556 1.0000 Uani . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0051 0.0024 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 6.6484
'ILL Blue book'
H 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 -3.7409
'ILL Blue book'
N 0.0095 0.0049 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 9.3600
'ILL Blue book'
O 0.0162 0.0090 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 5.8050
'ILL Blue book'
S 0.1643 0.1778 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 2.8470
'ILL Blue book'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . S1 . H1 . 95.96(17) no
C8 . O3 . H3 . 114.39(14) no
C1 . N1 . C4 . 111.92(6) yes
C1 . N1 . C5 . 120.35(6) yes
C4 . N1 . C5 . 127.70(6) yes
N1 . C1 . C2 . 104.23(6) yes
N1 . C1 . C8 . 110.85(6) yes
C2 . C1 . C8 . 110.70(7) yes
N1 . C1 . H11 . 109.75(12) no
C2 . C1 . H11 . 112.85(13) no
C8 . C1 . H11 . 108.43(12) no
C1 . C2 . C3 . 104.10(7) yes
C1 . C2 . H21 . 111.24(16) no
C3 . C2 . H21 . 114.72(16) no
C1 . C2 . H22 . 110.32(16) no
C3 . C2 . H22 . 109.83(16) no
H21 . C2 . H22 . 106.7(2) no
C2 . C3 . C4 . 103.42(7) yes
C2 . C3 . H31 . 111.36(14) no
C4 . C3 . H31 . 109.10(16) no
C2 . C3 . H32 . 112.85(16) no
C4 . C3 . H32 . 112.07(14) no
H31 . C3 . H32 . 108.0(2) no
C3 . C4 . N1 . 102.09(6) yes
C3 . C4 . H41 . 113.02(14) no
N1 . C4 . H41 . 110.34(13) no
C3 . C4 . H42 . 111.73(15) no
N1 . C4 . H42 . 109.92(14) no
H41 . C4 . H42 . 109.54(19) no
N1 . C5 . O2 . 119.62(8) yes
N1 . C5 . C6 . 119.27(7) yes
O2 . C5 . C6 . 121.05(8) yes
C5 . C6 . C7 . 109.66(7) yes
C5 . C6 . C9 . 107.82(7) yes
C7 . C6 . C9 . 112.56(8) yes
C5 . C6 . H61 . 110.13(14) no
C7 . C6 . H61 . 107.68(14) no
C9 . C6 . H61 . 108.98(15) no
C6 . C7 . S1 . 113.09(8) yes
C6 . C7 . H71 . 111.31(14) no
S1 . C7 . H71 . 105.58(16) no
C6 . C7 . H72 . 110.64(16) no
S1 . C7 . H72 . 107.80(16) no
H71 . C7 . H72 . 108.2(2) no
C1 . C8 . O3 . 116.05(8) yes
C1 . C8 . O1 . 123.02(8) yes
O3 . C8 . O1 . 120.90(9) yes
C6 . C9 . H91 . 110.04(16) no
C6 . C9 . H92 . 110.47(16) no
H91 . C9 . H92 . 108.7(2) no
C6 . C9 . H93 . 110.53(19) no
H91 . C9 . H93 . 108.7(2) no
H92 . C9 . H93 . 108.3(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C7 . 1.811(2) yes
S1 . H1 . 1.329(4) no
O1 . C8 . 1.2112(13) yes
O2 . C5 . 1.2555(12) yes
O3 . C8 . 1.3220(13) yes
O3 . H3 . 1.011(2) no
N1 . C1 . 1.4597(9) yes
N1 . C4 . 1.4715(10) yes
N1 . C5 . 1.3311(9) yes
C1 . C2 . 1.5451(12) yes
C1 . C8 . 1.5270(11) yes
C1 . H11 . 1.1048(19) no
C2 . C3 . 1.5238(12) yes
C2 . H21 . 1.090(2) no
C2 . H22 . 1.088(2) no
C3 . C4 . 1.5262(12) yes
C3 . H31 . 1.103(2) no
C3 . H32 . 1.094(2) no
C4 . H41 . 1.089(2) no
C4 . H42 . 1.089(2) no
C5 . C6 . 1.5179(11) yes
C6 . C7 . 1.5279(12) yes
C6 . C9 . 1.5267(13) yes
C6 . H61 . 1.085(2) no
C7 . H71 . 1.090(3) no
C7 . H72 . 1.091(3) no
C9 . H91 . 1.089(2) no
C9 . H92 . 1.089(3) no
C9 . H93 . 1.090(3) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O3 . H3 . O2 3_545 169.7(2) 1.011(2) 1.580(2) 2.5818(12) yes
O3 . H3 . C5 3_545 153.81(16) 1.011(2) 2.593(2) 3.5286(12) yes
C4 . H41 . O1 1_655 171.02(19) 1.089(2) 2.509(2) 3.5884(12) yes
C4 . H42 . O1 2_556 140.70(18) 1.089(2) 2.490(2) 3.4038(12) yes
C7 . H71 . O3 3_555 132.0(2) 1.090(3) 2.465(2) 3.2956(12) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 1 3 x .
