# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_prhdiacid
_database_code_depnum_ccdc_archive 'CCDC 2457289'
loop_
_audit_author_name
_audit_author_address
'John D. Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2025-06-06 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;
_vrf_PLAT113_prhdiacid           
;
PROBLEM:  PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New  Space Group 
          P21/c Check       
RESPONSE: The molecule is close to centrosymmetric but the two carboxylic acid
 groups are not related by a centre. Refinement in the new space group with the
 a axis halved led to acid groups with almost equal CO bonds, which is not 
chemically realistic.
;
_audit_creation_date             2024-01-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
trans-3,3'-Azothiophene-2,2'-dicarboxylic acid
;
_chemical_formula_moiety         'C10 H6 N2 O4 S2'
_chemical_formula_sum            'C10 H6 N2 O4 S2'
_chemical_formula_weight         282.29
_chemical_melting_point          447
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4513(3)
_cell_length_b                   11.4497(4)
_cell_length_c                   12.7532(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.562(4)
_cell_angle_gamma                90
_cell_volume                     1087.99(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3719
_cell_measurement_theta_min      5.1710
_cell_measurement_theta_max      78.9740
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.420
_exptl_absorpt_coefficient_mu    4.560
_exptl_absorpt_correction_T_min  0.519
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7129
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.355
_diffrn_reflns_theta_min         5.192
_diffrn_ambient_temperature      130(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 100'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.887
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1741
_reflns_number_total             2099
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2099
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.158
_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/[σ²(Fo²)+(0.0638P)²+4.0266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1787
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S1 S 0.08922(13) 0.74880(8) 0.25870(7) 0.0210(3) Uani 1 1 d . . . . .
S2 S 0.41119(13) 0.24704(8) 0.72799(7) 0.0206(3) Uani 1 1 d . . . . .
O1 O 0.2061(4) 0.9163(2) 0.4297(2) 0.0279(7) Uani 1 1 d . . . . .
O2 O 0.3031(4) 0.7830(3) 0.5427(2) 0.0262(7) Uani 1 1 d . . . . .
H21 H 0.301(8) 0.707(6) 0.548(5) 0.058(19) Uiso 1 1 d . . . . .
O3 O 0.1542(4) 0.2042(3) 0.4625(2) 0.0261(7) Uani 1 1 d . . . . .
O4 O 0.3156(5) 0.0829(3) 0.5646(3) 0.0308(7) Uani 1 1 d . . . . .
H41 H 0.263(9) 0.032(6) 0.524(6) 0.07(2) Uiso 1 1 d . . . . .
N1 N 0.2465(4) 0.5566(3) 0.4940(3) 0.0186(7) Uani 1 1 d . . . . .
N2 N 0.2459(5) 0.4458(3) 0.4992(3) 0.0198(7) Uani 1 1 d . . . . .
C1 C 0.1717(5) 0.7186(3) 0.3816(3) 0.0187(8) Uani 1 1 d . . . . .
C2 C 0.1804(5) 0.5995(3) 0.3980(3) 0.0177(8) Uani 1 1 d . . . . .
C3 C 0.1183(6) 0.5332(3) 0.3105(3) 0.0210(8) Uani 1 1 d . . . . .
H3 H 0.102(6) 0.450(4) 0.313(4) 0.025(12) Uiso 1 1 d . . . . .
C4 C 0.0649(6) 0.6036(4) 0.2307(3) 0.0222(9) Uani 1 1 d . . . . .
H4 H 0.009(6) 0.581(4) 0.169(4) 0.021(11) Uiso 1 1 d . . . . .
C5 C 0.2264(5) 0.8135(3) 0.4514(3) 0.0199(8) Uani 1 1 d . . . . .
C6 C 0.3181(5) 0.2806(3) 0.6085(3) 0.0183(8) Uani 1 1 d . . . . .
C7 C 0.3118(5) 0.4008(3) 0.5941(3) 0.0182(8) Uani 1 1 d . . . . .
C8 C 0.3812(6) 0.4635(4) 0.6823(3) 0.0214(8) Uani 1 1 d . . . . .
H8 H 0.398(6) 0.548(4) 0.686(4) 0.024(12) Uiso 1 1 d . . . . .
C9 C 0.4389(6) 0.3916(4) 0.7592(3) 0.0221(8) Uani 1 1 d . . . . .
H9 H 0.498(6) 0.415(4) 0.822(4) 0.026(12) Uiso 1 1 d . . . . .
C10 C 0.2527(5) 0.1874(3) 0.5367(3) 0.0201(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 1.713(4) . ?
S1 C4 1.710(4) . ?
S2 C6 1.712(4) . ?
S2 C9 1.714(4) . ?
O1 C5 1.218(5) . ?
O2 H21 0.87(7) . ?
O2 C5 1.339(5) . ?
O3 C10 1.208(5) . ?
O4 H41 0.87(8) . ?
O4 C10 1.332(5) . ?
N1 N2 1.270(5) . ?
N1 C2 1.404(5) . ?
N2 C7 1.400(5) . ?
C1 C2 1.381(5) . ?
C1 C5 1.460(5) . ?
C2 C3 1.423(5) . ?
C3 H3 0.96(5) . ?
C3 C4 1.355(6) . ?
C4 H4 0.92(5) . ?
C6 C7 1.389(5) . ?
C6 C10 1.485(5) . ?
C7 C8 1.427(5) . ?
C8 H8 0.98(5) . ?
C8 C9 1.348(6) . ?
C9 H9 0.95(5) . ?

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
C4 S1 C1 91.76(19) . . ?
C6 S2 C9 92.11(19) . . ?
C5 O2 H21 108(4) . . ?
C10 O4 H41 107(4) . . ?
N2 N1 C2 113.1(3) . . ?
N1 N2 C7 114.3(3) . . ?
C2 C1 S1 110.7(3) . . ?
C2 C1 C5 129.0(4) . . ?
C5 C1 S1 120.2(3) . . ?
N1 C2 C3 127.3(3) . . ?
C1 C2 N1 119.6(3) . . ?
C1 C2 C3 113.2(3) . . ?
C2 C3 H3 123(3) . . ?
C4 C3 C2 111.2(4) . . ?
C4 C3 H3 126(3) . . ?
S1 C4 H4 120(3) . . ?
C3 C4 S1 113.1(3) . . ?
C3 C4 H4 127(3) . . ?
O1 C5 O2 120.0(4) . . ?
O1 C5 C1 123.2(4) . . ?
O2 C5 C1 116.8(3) . . ?
C7 C6 S2 110.7(3) . . ?
C7 C6 C10 128.3(4) . . ?
C10 C6 S2 121.0(3) . . ?
N2 C7 C8 128.1(3) . . ?
C6 C7 N2 119.4(3) . . ?
C6 C7 C8 112.5(3) . . ?
C7 C8 H8 125(3) . . ?
C9 C8 C7 112.1(4) . . ?
C9 C8 H8 122(3) . . ?
S2 C9 H9 122(3) . . ?
C8 C9 S2 112.6(3) . . ?
C8 C9 H9 126(3) . . ?
O3 C10 O4 124.2(4) . . ?
O3 C10 C6 124.2(4) . . ?
O4 C10 C6 111.6(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H21 N1 0.87(7) 1.89(7) 2.698(4) 152(6) . yes
O4 H41 O1 0.87(8) 1.84(8) 2.691(4) 166(6) 1_545 yes

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 C2 N1 179.3(3) . . . . ?
S1 C1 C2 C3 -0.5(5) . . . . ?
S1 C1 C5 O1 4.9(6) . . . . ?
S1 C1 C5 O2 -174.7(3) . . . . ?
S2 C6 C7 N2 177.7(3) . . . . ?
S2 C6 C7 C8 -0.9(4) . . . . ?
S2 C6 C10 O3 164.1(3) . . . . ?
S2 C6 C10 O4 -15.6(5) . . . . ?
N1 N2 C7 C6 -179.8(4) . . . . ?
N1 N2 C7 C8 -1.5(6) . . . . ?
N1 C2 C3 C4 -179.7(4) . . . . ?
N2 N1 C2 C1 179.5(4) . . . . ?
N2 N1 C2 C3 -0.8(6) . . . . ?
N2 C7 C8 C9 -177.7(4) . . . . ?
C1 S1 C4 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 N1 N2 C7 179.8(3) . . . . ?
C2 C1 C5 O1 -177.2(4) . . . . ?
C2 C1 C5 O2 3.3(6) . . . . ?
C2 C3 C4 S1 0.4(5) . . . . ?
C4 S1 C1 C2 0.6(3) . . . . ?
C4 S1 C1 C5 178.8(3) . . . . ?
C5 C1 C2 N1 1.2(6) . . . . ?
C5 C1 C2 C3 -178.6(4) . . . . ?
C6 S2 C9 C8 -0.3(4) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C7 C6 C10 O3 -14.2(7) . . . . ?
C7 C6 C10 O4 166.1(4) . . . . ?
C7 C8 C9 S2 -0.1(5) . . . . ?
C9 S2 C6 C7 0.7(3) . . . . ?
C9 S2 C6 C10 -177.9(3) . . . . ?
C10 C6 C7 N2 -3.9(6) . . . . ?
C10 C6 C7 C8 177.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF/Toluene'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PRHdiesterorange
_database_code_depnum_ccdc_archive 'CCDC 2457290'
loop_
_audit_author_name
_audit_author_address
'John D. Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2025-06-06 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;
_audit_creation_date             2024-07-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;

_vrf_PLAT002_PRHdiesterorange    
;
PROBLEM:  Number of Distance or Angle Restraints on AtSite 30 Note 
RESPONSE: A small percentage (4.3) of an alternative orientation of
the molecule across a different centre of symmetry was included in 
the refinement. The two orientations were related by a series of SADI 
instructions generated by OLEX and corresponding ADPs were subject to
EADP commands.
;

_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
;
orange polymorph
;
_chemical_name_systematic        
;
2,2'-Bis(methoxycarbonyl)-3,3'-azothiophene
;
_chemical_formula_moiety         'C12 H10 N2 O4 S2'
_chemical_formula_sum            'C12 H10 N2 O4 S2'
_chemical_formula_weight         310.34
_chemical_melting_point          475
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0514(2)
_cell_length_b                   7.63966(18)
_cell_length_c                   9.7827(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.546(2)
_cell_angle_gamma                90
_cell_volume                     654.79(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120
_cell_measurement_reflns_used    5542
_cell_measurement_theta_min      5.9270
_cell_measurement_theta_max      77.2260
_shelx_estimated_absorpt_T_max   0.655
_shelx_estimated_absorpt_T_min   0.435
_exptl_absorpt_coefficient_mu    3.844
_exptl_absorpt_correction_T_min  0.310
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7403
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.924
_diffrn_reflns_theta_min         5.957
_diffrn_ambient_temperature      120
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 100'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_method       'ω scans'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1265
_reflns_number_total             1323
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1323
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.048
_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/[σ²(Fo²)+(0.0569P)²+0.3241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0946
_refine_special_details          ?
_olex2_refinement_description    
;
A second orientation of the molecule across a different centre of
symmetry (4.3 per cent) was included in the refinement.
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1-C1 \\sim S1A-C1A
 with sigma of 0.02
 S1-C4 \\sim S1A-C4A
 with sigma of 0.02
 O1-C5 \\sim O1A-C5A
 with sigma of 0.02
 O2-C5 \\sim O2A-C5A
 with sigma of 0.02
 O2-C6 \\sim O2A-C6A
 with sigma of 0.02
 N1-C2 \\sim N1A-C2A
 with sigma of 0.02
 C1-C2 \\sim C1A-C2A
 with sigma of 0.02
 C1-C5 \\sim C1A-C5A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C3-H3 \\sim C3A-H3A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C4-H4 \\sim C4A-H4A
 with sigma of 0.02
 C6-H6A \\sim C6A-H6AA
 with sigma of 0.02
 C6-H6B \\sim C6A-H6AB
 with sigma of 0.02
 C6-H6C \\sim C6A-H6AC
 with sigma of 0.02
 S1-C2 \\sim S1A-C2A
 with sigma of 0.04
 S1-C3 \\sim S1A-C3A
 with sigma of 0.04
 S1-H4 \\sim S1A-H4A
 with sigma of 0.04
 S1-C5 \\sim S1A-C5A
 with sigma of 0.04
 O1-O2 \\sim O1A-O2A
 with sigma of 0.04
 O1-C1 \\sim O1A-C1A
 with sigma of 0.04
 O2-C1 \\sim O2A-C1A
 with sigma of 0.04
 O2-H6A \\sim O2A-H6AA
 with sigma of 0.04
 O2-H6B \\sim O2A-H6AB
 with sigma of 0.04
 O2-H6C \\sim O2A-H6AC
 with sigma of 0.04
 N1-C1 \\sim N1A-C1A
 with sigma of 0.04
 N1-C3 \\sim N1A-C3A
 with sigma of 0.04
 C1-C3 \\sim C1A-C3A
 with sigma of 0.04
 C1-C4 \\sim C1A-C4A
 with sigma of 0.04
 C2-H3 \\sim C2A-H3A
 with sigma of 0.04
 C2-C4 \\sim C2A-C4A
 with sigma of 0.04
 C2-C5 \\sim C2A-C5A
 with sigma of 0.04
 C3-H4 \\sim C3A-H4A
 with sigma of 0.04
 H3-C4 \\sim H3A-C4A
 with sigma of 0.04
 C5-C6 \\sim C5A-C6A
 with sigma of 0.04
 H6A-H6B \\sim H6AA-H6AB
 with sigma of 0.04
 H6A-H6C \\sim H6AA-H6AC
 with sigma of 0.04
 H6B-H6C \\sim H6AB-H6AC
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(S1) = Uanis(S1A)
Uanis(O1) = Uanis(O1A)
Uanis(O2) = Uanis(O2A)
Uanis(N1) = Uanis(N1A)
Uanis(C1) = Uanis(C1A)
Uanis(C2) = Uanis(C2A)
Uanis(C3) = Uanis(C3A)
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C6A)
4. Others
 Sof(S1A)=Sof(C4A)=Sof(H4A)=Sof(C1A)=Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(C5A)=
 Sof(N1A)=Sof(O1A)=Sof(O2A)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=1-FVAR(1)
 Sof(S1)=Sof(O1)=Sof(O2)=Sof(N1)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=
 Sof(H4)=Sof(C5)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C4A(H4A), C3A(H3A)
5.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C6A(H6AA,H6AB,H6AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S1 S 0.58910(4) 0.19862(6) 0.35474(4) 0.02734(18) Uani 0.9569(13) 1 d D . P A 1
O1 O 0.63588(15) 0.70676(17) 0.38700(16) 0.0351(3) Uani 0.9569(13) 1 d D . P A
1
O2 O 0.44329(13) 0.52578(17) 0.28805(14) 0.0319(3) Uani 0.9569(13) 1 d D . P A
1
N1 N 0.93035(15) 0.52273(19) 0.48374(15) 0.0249(3) Uani 0.9569(13) 1 d D . P A
1
C1 C 0.67699(19) 0.3978(2) 0.38949(18) 0.0247(4) Uani 0.9569(13) 1 d D . P A 1
C2 C 0.8323(2) 0.3772(2) 0.44962(18) 0.0231(4) Uani 0.9569(13) 1 d D . P A 1
C3 C 0.8753(2) 0.1990(2) 0.46978(19) 0.0257(4) Uani 0.9569(13) 1 d D . P A 1
H3 H 0.976646 0.160966 0.511030 0.031 Uiso 0.9569(13) 1 calc DR U P A 1
C4 C 0.7559(2) 0.0886(2) 0.42369(19) 0.0290(4) Uani 0.9569(13) 1 d D . P A 1
H4 H 0.763824 -0.035369 0.429051 0.035 Uiso 0.9569(13) 1 calc DR U P A 1
C5 C 0.58859(17) 0.5621(2) 0.35662(17) 0.0259(4) Uani 0.9569(13) 1 d D . P A 1
C6 C 0.3444(2) 0.6762(3) 0.2484(2) 0.0345(4) Uani 0.9569(13) 1 d D . P A 1
H6A H 0.384733 0.751812 0.185313 0.052 Uiso 0.9569(13) 1 calc DR U P A 1
H6B H 0.339907 0.741889 0.333293 0.052 Uiso 0.9569(13) 1 calc DR U P A 1
H6C H 0.241638 0.636767 0.199658 0.052 Uiso 0.9569(13) 1 calc DR U P A 1
S1A S 0.5921(10) 0.3138(15) 0.3572(10) 0.02734(18) Uani 0.0431(13) 1 d D . P A
2
C4A C 0.762(3) 0.415(3) 0.419(4) 0.0290(4) Uani 0.0431(13) 1 d D . P A 2
H4A H 0.775296 0.538857 0.421120 0.035 Uiso 0.0431(13) 1 calc DR U P A 2
C1A C 0.675(2) 0.111(2) 0.389(4) 0.0247(4) Uani 0.0431(13) 1 d D . P A 2
C3A C 0.874(3) 0.300(4) 0.465(4) 0.0257(4) Uani 0.0431(13) 1 d D . P A 2
H3A H 0.976592 0.334118 0.506071 0.031 Uiso 0.0431(13) 1 calc DR U P A 2
C2A C 0.830(3) 0.123(3) 0.447(4) 0.0231(4) Uani 0.0431(13) 1 d D . P A 2
C5A C 0.589(2) -0.057(3) 0.359(3) 0.0259(4) Uani 0.0431(13) 1 d D . P A 2
N1A N 0.931(3) -0.022(3) 0.480(3) 0.0249(3) Uani 0.0431(13) 1 d D . P A 2
O1A O 0.645(3) -0.195(3) 0.391(4) 0.0351(3) Uani 0.0431(13) 1 d D . P A 2
O2A O 0.444(2) -0.036(3) 0.286(3) 0.0319(3) Uani 0.0431(13) 1 d D . P A 2
C6A C 0.357(3) -0.196(4) 0.249(4) 0.0345(4) Uani 0.0431(13) 1 d D . P A 2
H6AA H 0.356783 -0.261304 0.335028 0.052 Uiso 0.0431(13) 1 calc DR U P A 2
H6AB H 0.403936 -0.267692 0.188021 0.052 Uiso 0.0431(13) 1 calc DR U P A 2
H6AC H 0.252081 -0.167180 0.198602 0.052 Uiso 0.0431(13) 1 calc DR U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 1.7113(17) . ?
S1 C4 1.7114(19) . ?
O1 C5 1.196(2) . ?
O2 C5 1.3466(19) . ?
O2 C6 1.449(2) . ?
N1 N1 1.269(3) 3_766 ?
N1 C2 1.410(2) . ?
C1 C2 1.390(2) . ?
C1 C5 1.480(2) . ?
C2 C3 1.416(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.356(3) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
S1A C4A 1.691(17) . ?
S1A C1A 1.712(17) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.340(16) . ?
C1A C2A 1.382(17) . ?
C1A C5A 1.487(16) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.402(17) . ?
C2A N1A 1.424(17) . ?
C5A O1A 1.182(17) . ?
C5A O2A 1.337(17) . ?
N1A N1A 1.26(5) 3_756 ?
O2A C6A 1.453(16) . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?

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 C4 92.21(9) . . ?
C5 O2 C6 115.51(14) . . ?
N1 N1 C2 111.74(18) 3_766 . ?
C2 C1 S1 110.71(13) . . ?
C2 C1 C5 128.50(16) . . ?
C5 C1 S1 120.79(13) . . ?
N1 C2 C3 126.20(17) . . ?
C1 C2 N1 121.37(16) . . ?
C1 C2 C3 112.43(15) . . ?
C2 C3 H3 123.7 . . ?
C4 C3 C2 112.53(16) . . ?
C4 C3 H3 123.7 . . ?
S1 C4 H4 124.0 . . ?
C3 C4 S1 112.10(14) . . ?
C3 C4 H4 124.0 . . ?
O1 C5 O2 123.91(16) . . ?
O1 C5 C1 126.14(15) . . ?
O2 C5 C1 109.93(15) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4A S1A C1A 92.0(11) . . ?
S1A C4A H4A 124.4 . . ?
C3A C4A S1A 111.2(15) . . ?
C3A C4A H4A 124.4 . . ?
C2A C1A S1A 111.5(13) . . ?
C2A C1A C5A 124.2(16) . . ?
C5A C1A S1A 124.3(15) . . ?
C4A C3A H3A 122.5 . . ?
C4A C3A C2A 115.0(17) . . ?
C2A C3A H3A 122.5 . . ?
C1A C2A C3A 110.2(16) . . ?
C1A C2A N1A 125(2) . . ?
C3A C2A N1A 125(2) . . ?
O1A C5A C1A 124(2) . . ?
O1A C5A O2A 123(2) . . ?
O2A C5A C1A 113.1(17) . . ?
N1A N1A C2A 113(3) 3_756 . ?
C5A O2A C6A 115.5(19) . . ?
O2A C6A H6AA 109.5 . . ?
O2A C6A H6AB 109.5 . . ?
O2A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?

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 C2 N1 177.99(12) . . . . ?
S1 C1 C2 C3 -1.72(19) . . . . ?
S1 C1 C5 O1 173.42(15) . . . . ?
S1 C1 C5 O2 -5.6(2) . . . . ?
N1 N1 C2 C1 -169.59(17) 3_766 . . . ?
N1 N1 C2 C3 10.1(3) 3_766 . . . ?
N1 C2 C3 C4 -178.63(16) . . . . ?
C1 S1 C4 C3 -0.93(14) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C2 C1 C5 O1 -6.1(3) . . . . ?
C2 C1 C5 O2 174.85(15) . . . . ?
C2 C3 C4 S1 0.1(2) . . . . ?
C4 S1 C1 C2 1.50(14) . . . . ?
C4 S1 C1 C5 -178.12(15) . . . . ?
C5 C1 C2 N1 -2.4(3) . . . . ?
C5 C1 C2 C3 177.87(16) . . . . ?
C6 O2 C5 O1 1.5(2) . . . . ?
C6 O2 C5 C1 -179.45(14) . . . . ?
S1A C4A C3A C2A 2(6) . . . . ?
S1A C1A C2A C3A 1(5) . . . . ?
S1A C1A C2A N1A -178(3) . . . . ?
S1A C1A C5A O1A -174(3) . . . . ?
S1A C1A C5A O2A 9(5) . . . . ?
C4A S1A C1A C2A 0(3) . . . . ?
C4A S1A C1A C5A 180(4) . . . . ?
C4A C3A C2A C1A -2(6) . . . . ?
C4A C3A C2A N1A 176(4) . . . . ?
C1A S1A C4A C3A -1(4) . . . . ?
C1A C2A N1A N1A 174(4) . . . 3_756 ?
C1A C5A O2A C6A 178(3) . . . . ?
C3A C2A N1A N1A -4(7) . . . 3_756 ?
C2A C1A C5A O1A 6(6) . . . . ?
C2A C1A C5A O2A -172(4) . . . . ?
C5A C1A C2A C3A -179(4) . . . . ?
C5A C1A C2A N1A 3(7) . . . . ?
O1A C5A O2A C6A 1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_prhdiestercolourless
_database_code_depnum_ccdc_archive 'CCDC 2457291'
loop_
_audit_author_name
_audit_author_address
'John D. Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2025-06-06 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;
_audit_creation_date             2025-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7181)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
;
Colourless polymorph
;
_chemical_name_systematic        
;
2,2'-Bis(methoxycarbonyl)-3,3'-azothiophene
;
_chemical_formula_moiety         'C12 H10 N2 O4 S2'
_chemical_formula_sum            'C12 H10 N2 O4 S2'
_chemical_formula_weight         310.34
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.87346(11)
_cell_length_b                   13.8361(6)
_cell_length_c                   13.9032(6)
_cell_angle_alpha                61.541(4)
_cell_angle_beta                 87.776(3)
_cell_angle_gamma                87.828(3)
_cell_volume                     654.43(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    119.99(10)
_cell_measurement_reflns_used    3644
_cell_measurement_theta_min      3.5560
_cell_measurement_theta_max      79.0590
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.423
_exptl_absorpt_coefficient_mu    3.846
_exptl_absorpt_correction_T_min  0.398
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.115a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.043
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8998
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.568
_diffrn_reflns_theta_min         3.617
_diffrn_ambient_temperature      119.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 100'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.873
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2056
_reflns_number_total             2469
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrysAlisPro system (CCD 43.115a 64-bit (release 15-03-2024))
;
_computing_cell_refinement       'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.044
_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/[σ²(Fo²)+(0.0274P)²+0.5998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1060
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
S1 S 0.37607(16) 0.77796(5) 0.45611(5) 0.02414(19) Uani 1 1 d . . . . .
S11 S 1.30069(16) 0.24028(5) 1.02048(5) 0.02591(19) Uani 1 1 d . . . . .
O1 O 0.5347(6) 0.75295(17) 0.74359(17) 0.0393(5) Uani 1 1 d . . . . .
O2 O 0.2745(5) 0.87809(15) 0.59169(15) 0.0299(4) Uani 1 1 d . . . . .
O11 O 0.9034(5) 0.24072(16) 0.76600(16) 0.0330(5) Uani 1 1 d . . . . .
O12 O 1.2253(5) 0.11892(15) 0.90491(15) 0.0287(4) Uani 1 1 d . . . . .
N1 N 0.8064(5) 0.55810(18) 0.72698(17) 0.0224(5) Uani 1 1 d . . . . .
N11 N 0.9189(5) 0.46424(18) 0.74317(17) 0.0229(5) Uani 1 1 d . . . . .
C1 C 0.5127(6) 0.7227(2) 0.5886(2) 0.0208(5) Uani 1 1 d . . . . .
C2 C 0.6704(6) 0.6207(2) 0.6215(2) 0.0203(5) Uani 1 1 d . . . . .
C3 C 0.6767(6) 0.5889(2) 0.5381(2) 0.0237(6) Uani 1 1 d . . . . .
H3 H 0.774003 0.521298 0.546587 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5283(7) 0.6659(2) 0.4452(2) 0.0259(6) Uani 1 1 d . . . . .
H4 H 0.510654 0.658496 0.381075 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4468(7) 0.7822(2) 0.6515(2) 0.0260(6) Uani 1 1 d . . . . .
C6 C 0.1917(8) 0.9418(3) 0.6474(3) 0.0353(7) Uani 1 1 d . . . . .
H6A H 0.053853 1.007037 0.599734 0.053 Uiso 1 1 calc R U . . .
H6B H 0.405766 0.964544 0.665375 0.053 Uiso 1 1 calc R U . . .
H6C H 0.059260 0.896882 0.714882 0.053 Uiso 1 1 calc R U . . .
C11 C 1.1304(6) 0.2908(2) 0.8927(2) 0.0227(6) Uani 1 1 d . . . . .
C12 C 1.0618(6) 0.4031(2) 0.8477(2) 0.0212(5) Uani 1 1 d . . . . .
C13 C 1.1572(7) 0.4463(2) 0.9171(2) 0.0259(6) Uani 1 1 d . . . . .
H13 H 1.132270 0.521717 0.898725 0.031 Uiso 1 1 calc R U . . .
C14 C 1.2881(7) 0.3673(2) 1.0127(2) 0.0273(6) Uani 1 1 d . . . . .
H14 H 1.364171 0.381222 1.069060 0.033 Uiso 1 1 calc R U . . .
C15 C 1.0691(6) 0.2184(2) 0.8452(2) 0.0239(6) Uani 1 1 d . . . . .
C16 C 1.1910(8) 0.0426(2) 0.8625(3) 0.0339(7) Uani 1 1 d . . . . .
H16A H 1.299229 0.072873 0.789346 0.051 Uiso 1 1 calc R U . . .
H16B H 0.945518 0.030697 0.858234 0.051 Uiso 1 1 calc R U . . .
H16C H 1.305031 -0.027577 0.911277 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 1.721(3) . ?
S1 C4 1.709(3) . ?
S11 C11 1.719(3) . ?
S11 C14 1.708(3) . ?
O1 C5 1.203(3) . ?
O2 C5 1.350(3) . ?
O2 C6 1.445(3) . ?
O11 C15 1.199(3) . ?
O12 C15 1.356(3) . ?
O12 C16 1.446(3) . ?
N1 N11 1.270(3) . ?
N1 C2 1.411(3) . ?
N11 C12 1.411(3) . ?
C1 C2 1.383(4) . ?
C1 C5 1.470(4) . ?
C2 C3 1.423(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.354(4) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C11 C12 1.390(4) . ?
C11 C15 1.467(4) . ?
C12 C13 1.421(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.358(4) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C4 S1 C1 91.88(13) . . ?
C14 S11 C11 92.17(13) . . ?
C5 O2 C6 115.2(2) . . ?
C15 O12 C16 114.7(2) . . ?
N11 N1 C2 112.1(2) . . ?
N1 N11 C12 111.8(2) . . ?
C2 C1 S1 110.84(19) . . ?
C2 C1 C5 128.9(2) . . ?
C5 C1 S1 120.2(2) . . ?
N1 C2 C3 125.5(2) . . ?
C1 C2 N1 122.1(2) . . ?
C1 C2 C3 112.4(2) . . ?
C2 C3 H3 123.8 . . ?
C4 C3 C2 112.3(2) . . ?
C4 C3 H3 123.8 . . ?
S1 C4 H4 123.7 . . ?
C3 C4 S1 112.5(2) . . ?
C3 C4 H4 123.7 . . ?
O1 C5 O2 122.7(2) . . ?
O1 C5 C1 126.3(3) . . ?
O2 C5 C1 111.1(2) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C11 S11 110.49(19) . . ?
C12 C11 C15 128.2(2) . . ?
C15 C11 S11 121.3(2) . . ?
N11 C12 C13 125.6(2) . . ?
C11 C12 N11 121.6(2) . . ?
C11 C12 C13 112.7(2) . . ?
C12 C13 H13 123.9 . . ?
C14 C13 C12 112.1(3) . . ?
C14 C13 H13 123.9 . . ?
S11 C14 H14 123.7 . . ?
C13 C14 S11 112.5(2) . . ?
C13 C14 H14 123.7 . . ?
O11 C15 O12 123.1(2) . . ?
O11 C15 C11 126.5(3) . . ?
O12 C15 C11 110.3(2) . . ?
O12 C16 H16A 109.5 . . ?
O12 C16 H16B 109.5 . . ?
O12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 C2 N1 179.82(18) . . . . ?
S1 C1 C2 C3 -0.2(3) . . . . ?
S1 C1 C5 O1 -178.6(2) . . . . ?
S1 C1 C5 O2 0.4(3) . . . . ?
S11 C11 C12 N11 -179.72(17) . . . . ?
S11 C11 C12 C13 1.5(3) . . . . ?
S11 C11 C15 O11 167.2(2) . . . . ?
S11 C11 C15 O12 -12.1(3) . . . . ?
N1 N11 C12 C11 165.6(2) . . . . ?
N1 N11 C12 C13 -15.8(3) . . . . ?
N1 C2 C3 C4 -179.7(2) . . . . ?
N11 N1 C2 C1 175.6(2) . . . . ?
N11 N1 C2 C3 -4.4(3) . . . . ?
N11 C12 C13 C14 -179.9(2) . . . . ?
C1 S1 C4 C3 0.2(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 N1 N11 C12 178.62(19) . . . . ?
C2 C1 C5 O1 3.3(5) . . . . ?
C2 C1 C5 O2 -177.7(2) . . . . ?
C2 C3 C4 S1 -0.3(3) . . . . ?
C4 S1 C1 C2 0.01(19) . . . . ?
C4 S1 C1 C5 -178.4(2) . . . . ?
C5 C1 C2 N1 -2.0(4) . . . . ?
C5 C1 C2 C3 178.0(2) . . . . ?
C6 O2 C5 O1 -2.1(4) . . . . ?
C6 O2 C5 C1 178.9(2) . . . . ?
C11 S11 C14 C13 0.4(2) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?
C12 C11 C15 O11 -11.5(4) . . . . ?
C12 C11 C15 O12 169.2(2) . . . . ?
C12 C13 C14 S11 0.3(3) . . . . ?
C14 S11 C11 C12 -1.10(19) . . . . ?
C14 S11 C11 C15 180.0(2) . . . . ?
C15 C11 C12 N11 -0.9(4) . . . . ?
C15 C11 C12 C13 -179.7(2) . . . . ?
C16 O12 C15 O11 2.9(4) . . . . ?
C16 O12 C15 C11 -177.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
