# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_thio-nh-ts
_database_code_depnum_ccdc_archive 'CCDC 2068059'
loop_
_audit_author_name
_audit_author_address
'Christophe Vande Velde'
;University of Antwerp
Belgium
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
methyl 3-(p-tolylsulfonylamino)thiophene-2-carboxylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 N O4 S2'
_chemical_formula_sum            'C13 H13 N O4 S2'
_chemical_formula_weight         311.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5382(11)
_cell_length_b                   7.5215(7)
_cell_length_c                   15.2868(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.455(9)
_cell_angle_gamma                90
_cell_volume                     1437.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    19138
_cell_measurement_theta_min      3.536
_cell_measurement_theta_max      71.725

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    3.481
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7239
_exptl_absorpt_correction_T_max  1.3418
_exptl_absorpt_process_details   'HKL3000 v2.3.10 (Minor & Otwinowski, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Rigaku R-Axis II'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            39751
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.806
_diffrn_reflns_theta_max         71.799
_diffrn_reflns_theta_full        67.700
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             2671
_reflns_number_gt                2162
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Rigaku CrystalClear 2.1 (Rigaku, 2014)'
_computing_cell_refinement       'HKL3000 v2.3.10 (Minor & Otwinowski, 1997)'
_computing_data_reduction        'HKL3000 v2.3.10 (Minor & Otwinowski, 1997)'
_computing_structure_solution    'SHELXT-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0987P)²+1.0485P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2671
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1807
_refine_ls_wR_factor_gt          0.1678
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.47633(8) 0.84897(12) 0.36727(7) 0.0692(3) Uani 1 1 d . . . . .
H3 H 0.608(4) 0.362(6) 0.427(3) 0.097(15) Uiso 1 1 d . . . . .
C3 C 0.6130(3) 0.6193(4) 0.4278(2) 0.0524(7) Uani 1 1 d . . . . .
N3 N 0.6569(2) 0.4530(4) 0.4527(2) 0.0617(8) Uani 1 1 d . . . . .
O3 O 0.7875(2) 0.2173(4) 0.4722(2) 0.0859(9) Uani 1 1 d . . . . .
C2 C 0.5137(2) 0.6307(4) 0.3836(2) 0.0519(7) Uani 1 1 d . . . . .
S2 S 0.78439(7) 0.40612(13) 0.46020(6) 0.0643(3) Uani 1 1 d . . . . .
O2 O 0.8380(2) 0.5192(5) 0.52404(19) 0.0879(9) Uani 1 1 d . . . . .
C4 C 0.6595(3) 0.7869(5) 0.4468(3) 0.0665(9) Uani 1 1 d . . . . .
H4 H 0.726708 0.804113 0.475753 0.080 Uiso 1 1 calc R U . . .
C5 C 0.5927(3) 0.9202(5) 0.4172(3) 0.0746(11) Uani 1 1 d . . . . .
H5 H 0.609947 1.039976 0.424030 0.090 Uiso 1 1 calc R U . . .
O6 O 0.4714(2) 0.3268(3) 0.36844(18) 0.0701(7) Uani 1 1 d . . . . .
C6 C 0.4462(3) 0.4808(4) 0.3557(2) 0.0552(8) Uani 1 1 d . . . . .
O7 O 0.35393(19) 0.5314(3) 0.31372(18) 0.0697(7) Uani 1 1 d . . . . .
C7 C 0.2786(4) 0.3902(7) 0.2876(3) 0.0892(14) Uani 1 1 d . . . . .
H7A H 0.221172 0.437942 0.249497 0.134 Uiso 1 1 calc R U . . .
H7B H 0.250280 0.340503 0.338825 0.134 Uiso 1 1 calc R U . . .
H7C H 0.314631 0.299012 0.257304 0.134 Uiso 1 1 calc R U . . .
C11 C 0.8309(2) 0.4589(4) 0.3578(2) 0.0524(7) Uani 1 1 d . . . . .
C13 C 0.9605(3) 0.5939(5) 0.2724(3) 0.0733(11) Uani 1 1 d . . . . .
H13 H 1.021813 0.662423 0.269474 0.088 Uiso 1 1 calc R U . . .
C12 C 0.9226(3) 0.5605(5) 0.3532(3) 0.0673(10) Uani 1 1 d . . . . .
H12 H 0.958125 0.605787 0.404096 0.081 Uiso 1 1 calc R U . . .
C14 C 0.9096(3) 0.5281(4) 0.1961(3) 0.0602(8) Uani 1 1 d . . . . .
C15 C 0.8179(3) 0.4267(5) 0.2014(3) 0.0614(9) Uani 1 1 d . . . . .
H15 H 0.782388 0.381866 0.150499 0.074 Uiso 1 1 calc R U . . .
C16 C 0.7791(3) 0.3920(4) 0.2815(2) 0.0595(9) Uani 1 1 d . . . . .
H16 H 0.717829 0.323209 0.284404 0.071 Uiso 1 1 calc R U . . .
C17 C 0.9530(4) 0.5639(7) 0.1081(3) 0.0860(13) Uani 1 1 d . . . . .
H17A H 0.923490 0.479368 0.065881 0.129 Uiso 1 1 calc R U . . .
H17B H 1.029550 0.553105 0.113611 0.129 Uiso 1 1 calc R U . . .
H17C H 0.933579 0.681975 0.089127 0.129 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 C5 1.682(4) . ?
S1 C2 1.720(3) . ?
C3 C2 1.372(4) . ?
C3 N3 1.407(4) . ?
C3 C4 1.410(5) . ?
N3 S2 1.632(3) . ?
O3 S2 1.432(3) . ?
C2 C6 1.454(4) . ?
S2 O2 1.423(3) . ?
S2 C11 1.758(4) . ?
C4 C5 1.361(5) . ?
O6 C6 1.212(4) . ?
C6 O7 1.334(4) . ?
O7 C7 1.456(4) . ?
C11 C16 1.384(4) . ?
C11 C12 1.387(5) . ?
C13 C14 1.378(5) . ?
C13 C12 1.380(6) . ?
C14 C15 1.387(5) . ?
C14 C17 1.513(6) . ?
C15 C16 1.378(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
C5 S1 C2 91.21(17) . . ?
C2 C3 N3 120.7(3) . . ?
C2 C3 C4 113.0(3) . . ?
N3 C3 C4 126.3(3) . . ?
C3 N3 S2 124.9(2) . . ?
C3 C2 C6 125.5(3) . . ?
C3 C2 S1 111.0(2) . . ?
C6 C2 S1 123.5(2) . . ?
O2 S2 O3 119.9(2) . . ?
O2 S2 N3 109.10(18) . . ?
O3 S2 N3 103.88(17) . . ?
O2 S2 C11 107.69(18) . . ?
O3 S2 C11 109.30(18) . . ?
N3 S2 C11 106.23(15) . . ?
C5 C4 C3 110.9(3) . . ?
C4 C5 S1 113.9(3) . . ?
O6 C6 O7 123.8(3) . . ?
O6 C6 C2 123.7(3) . . ?
O7 C6 C2 112.6(3) . . ?
C6 O7 C7 116.3(3) . . ?
C16 C11 C12 119.7(3) . . ?
C16 C11 S2 120.1(3) . . ?
C12 C11 S2 120.2(3) . . ?
C14 C13 C12 121.6(3) . . ?
C13 C12 C11 119.3(3) . . ?
C13 C14 C15 118.6(4) . . ?
C13 C14 C17 120.9(3) . . ?
C15 C14 C17 120.5(4) . . ?
C16 C15 C14 120.6(3) . . ?
C15 C16 C11 120.3(3) . . ?

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
C2 C3 N3 S2 148.6(3) . . . . ?
C4 C3 N3 S2 -34.2(5) . . . . ?
N3 C3 C2 C6 -2.0(5) . . . . ?
C4 C3 C2 C6 -179.5(3) . . . . ?
N3 C3 C2 S1 176.3(3) . . . . ?
C4 C3 C2 S1 -1.2(4) . . . . ?
C5 S1 C2 C3 1.0(3) . . . . ?
C5 S1 C2 C6 179.3(3) . . . . ?
C3 N3 S2 O2 60.8(4) . . . . ?
C3 N3 S2 O3 -170.3(3) . . . . ?
C3 N3 S2 C11 -55.1(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
N3 C3 C4 C5 -176.5(4) . . . . ?
C3 C4 C5 S1 -0.1(5) . . . . ?
C2 S1 C5 C4 -0.5(4) . . . . ?
C3 C2 C6 O6 -0.5(6) . . . . ?
S1 C2 C6 O6 -178.6(3) . . . . ?
C3 C2 C6 O7 -179.8(3) . . . . ?
S1 C2 C6 O7 2.1(4) . . . . ?
O6 C6 O7 C7 4.0(5) . . . . ?
C2 C6 O7 C7 -176.7(3) . . . . ?
O2 S2 C11 C16 -168.6(3) . . . . ?
O3 S2 C11 C16 59.7(3) . . . . ?
N3 S2 C11 C16 -51.8(3) . . . . ?
O2 S2 C11 C12 14.5(3) . . . . ?
O3 S2 C11 C12 -117.2(3) . . . . ?
N3 S2 C11 C12 131.3(3) . . . . ?
C14 C13 C12 C11 -0.2(6) . . . . ?
C16 C11 C12 C13 0.2(5) . . . . ?
S2 C11 C12 C13 177.1(3) . . . . ?
C12 C13 C14 C15 0.3(6) . . . . ?
C12 C13 C14 C17 -179.2(4) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C17 C14 C15 C16 179.1(4) . . . . ?
C14 C15 C16 C11 0.4(5) . . . . ?
C12 C11 C16 C15 -0.3(5) . . . . ?
S2 C11 C16 C15 -177.2(3) . . . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.075


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_s2nhtsi
_database_code_depnum_ccdc_archive 'CCDC 2068060'
loop_
_audit_author_name
_audit_author_address
'Christophe Vande Velde'
;University of Antwerp
Belgium
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"Methyl 4-[[(4-methylphenyl)sulfonyl]amino][2,2'-bithiophene]-5-carboxylate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N O4 S3'
_chemical_formula_sum            'C17 H15 N O4 S3'
_chemical_formula_weight         393.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        I2/c
_space_group_name_Hall           '-I 2yc'

_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   19.992(6)
_cell_length_b                   12.0910(17)
_cell_length_c                   30.161(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.166(16)
_cell_angle_gamma                90
_cell_volume                     7249(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    23472
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      89.69

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             3264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    3.935
_shelx_estimated_absorpt_T_min   0.5117
_shelx_estimated_absorpt_T_max   1.4148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5117
_exptl_absorpt_correction_T_max  1.4148
_exptl_absorpt_process_details   'SCALEPACK (Otinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Rigaku RAPID II'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39268
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.942
_diffrn_reflns_theta_max         71.840
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             6888
_reflns_number_gt                5742
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear 2.0'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0729P)²+7.1080P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00040(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6888
_refine_ls_number_parameters     464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


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 0.41772(4) 0.83944(6) 0.57619(2) 0.0692(2) Uani 1 1 d . . . . .
O1 O 0.33015(12) 0.65369(18) 0.59399(8) 0.0835(6) Uani 1 1 d . . . . .
N1 N 0.52350(16) 0.5762(2) 0.55449(11) 0.0791(8) Uani 1 1 d . . . . .
H1 H 0.4973(19) 0.530(3) 0.5592(12) 0.095(13) Uiso 1 1 d . . . . .
C1 C 0.43448(16) 0.7003(2) 0.57175(9) 0.0655(7) Uani 1 1 d . . . . .
S2 S 0.59700(5) 1.02398(8) 0.55189(4) 0.0961(3) Uani 1 1 d . . . . .
O2 O 0.39969(12) 0.51581(18) 0.57858(8) 0.0829(6) Uani 1 1 d . . . . .
C2 C 0.49890(16) 0.6831(2) 0.56063(9) 0.0655(7) Uani 1 1 d . . . . .
S3 S 0.60197(4) 0.53848(6) 0.55577(3) 0.0705(2) Uani 1 1 d . . . . .
O3 O 0.63495(13) 0.61325(18) 0.52918(7) 0.0869(7) Uani 1 1 d . . . . .
C3 C 0.53433(17) 0.7828(2) 0.55588(10) 0.0696(7) Uani 1 1 d . . . . .
H3 H 0.578254 0.786000 0.548464 0.083 Uiso 1 1 calc R U . . .
C4 C 0.49695(15) 0.8738(2) 0.56338(9) 0.0626(7) Uani 1 1 d . . . . .
O4 O 0.59871(13) 0.42374(17) 0.54538(8) 0.0868(7) Uani 1 1 d . . . . .
C5 C 0.51726(16) 0.9898(2) 0.56152(9) 0.0650(7) Uani 1 1 d . . . . .
C6 C 0.47845(17) 1.0836(2) 0.56660(11) 0.0736(8) Uani 1 1 d . . . . .
H6 H 0.433498 1.082882 0.571953 0.088 Uiso 1 1 calc R U . . .
C7 C 0.5175(2) 1.1812(3) 0.56244(12) 0.0871(10) Uani 1 1 d . . . . .
H7 H 0.500553 1.252238 0.565030 0.104 Uiso 1 1 calc R U . . .
C8 C 0.5806(2) 1.1607(3) 0.55448(12) 0.0870(10) Uani 1 1 d . . . . .
H8 H 0.612065 1.215594 0.550758 0.104 Uiso 1 1 calc R U . . .
C9 C 0.38814(17) 0.6139(3) 0.58120(9) 0.0699(8) Uani 1 1 d . . . . .
C10 C 0.28292(19) 0.5720(3) 0.60661(14) 0.0974(11) Uani 1 1 d . . . . .
H10A H 0.242186 0.608030 0.612862 0.146 Uiso 1 1 calc R U . . .
H10B H 0.302151 0.533319 0.632719 0.146 Uiso 1 1 calc R U . . .
H10C H 0.273048 0.520347 0.582619 0.146 Uiso 1 1 calc R U . . .
C11 C 0.63935(14) 0.5539(2) 0.61104(9) 0.0600(6) Uani 1 1 d . . . . .
C12 C 0.63007(15) 0.4735(2) 0.64238(10) 0.0654(7) Uani 1 1 d . . . . .
H12 H 0.602118 0.413399 0.634794 0.078 Uiso 1 1 calc R U . . .
C13 C 0.66243(15) 0.4828(2) 0.68490(10) 0.0680(7) Uani 1 1 d . . . . .
H13 H 0.655706 0.428701 0.705906 0.082 Uiso 1 1 calc R U . . .
C14 C 0.70483(14) 0.5710(2) 0.69706(10) 0.0654(7) Uani 1 1 d . . . . .
C15 C 0.71278(16) 0.6514(3) 0.66516(11) 0.0752(8) Uani 1 1 d . . . . .
H15 H 0.740402 0.711912 0.672699 0.090 Uiso 1 1 calc R U . . .
C16 C 0.68060(17) 0.6433(2) 0.62262(11) 0.0741(8) Uani 1 1 d . . . . .
H16 H 0.686595 0.697908 0.601694 0.089 Uiso 1 1 calc R U . . .
C17 C 0.74282(17) 0.5781(3) 0.74267(11) 0.0846(9) Uani 1 1 d . . . . .
H17A H 0.790029 0.585420 0.739987 0.127 Uiso 1 1 calc R U . . .
H17B H 0.735166 0.512091 0.759107 0.127 Uiso 1 1 calc R U . . .
H17C H 0.727572 0.641139 0.758090 0.127 Uiso 1 1 calc R U . . .
C21 C 0.45039(12) 0.9534(2) 0.31495(8) 0.0512(5) Uani 1 1 d . . . . .
O21 O 0.34298(9) 0.90382(16) 0.32850(7) 0.0691(5) Uani 1 1 d . . . . .
N21 N 0.54180(11) 0.83340(18) 0.29967(8) 0.0589(6) Uani 1 1 d . . . . .
H1A H 0.5184(16) 0.783(3) 0.3031(10) 0.072(10) Uiso 1 1 d . . . . .
S21 S 0.43027(3) 1.09126(5) 0.31852(2) 0.05533(18) Uani 1 1 d . . . . .
C23 C 0.55021(12) 1.04053(19) 0.30267(8) 0.0513(5) Uani 1 1 d . . . . .
H23 H 0.594800 1.046008 0.296767 0.062 Uiso 1 1 calc R U . . .
O23 O 0.65554(9) 0.87534(15) 0.27882(6) 0.0613(5) Uani 1 1 d . . . . .
S23 S 0.62076(3) 0.79806(5) 0.30376(2) 0.05234(18) Uani 1 1 d . . . . .
C22 C 0.51601(12) 0.93915(19) 0.30616(8) 0.0488(5) Uani 1 1 d . . . . .
O22 O 0.41647(9) 0.76705(15) 0.31892(7) 0.0653(5) Uani 1 1 d . . . . .
S22 S 0.60385(4) 1.28829(6) 0.29266(3) 0.0735(2) Uani 1 1 d . . . . .
C25 C 0.52761(12) 1.2467(2) 0.30750(8) 0.0510(5) Uani 1 1 d . . . . .
C24 C 0.51020(12) 1.12969(19) 0.30897(8) 0.0487(5) Uani 1 1 d . . . . .
O24 O 0.61972(10) 0.68382(15) 0.29271(7) 0.0672(5) Uani 1 1 d . . . . .
C27 C 0.52218(16) 1.4382(2) 0.31047(11) 0.0721(8) Uani 1 1 d . . . . .
H27 H 0.503464 1.507150 0.315012 0.086 Uiso 1 1 calc R U . . .
C26 C 0.48848(15) 1.3366(2) 0.31627(10) 0.0662(7) Uani 1 1 d . . . . .
H26 H 0.445329 1.331288 0.324922 0.079 Uiso 1 1 calc R U . . .
C28 C 0.58342(16) 1.4241(2) 0.29785(11) 0.0726(8) Uani 1 1 d . . . . .
H28 H 0.611958 1.482203 0.292454 0.087 Uiso 1 1 calc R U . . .
C29 C 0.40304(12) 0.8648(2) 0.32080(8) 0.0557(6) Uani 1 1 d . . . . .
C30 C 0.29161(16) 0.8212(3) 0.33297(15) 0.0956(12) Uani 1 1 d . . . . .
H30A H 0.288194 0.773114 0.307515 0.143 Uiso 1 1 calc R U . . .
H30B H 0.249176 0.857156 0.334826 0.143 Uiso 1 1 calc R U . . .
H30C H 0.303428 0.778739 0.359547 0.143 Uiso 1 1 calc R U . . .
C31 C 0.65222(12) 0.8123(2) 0.36014(8) 0.0519(5) Uani 1 1 d . . . . .
C32 C 0.64280(14) 0.7265(2) 0.38923(9) 0.0624(7) Uani 1 1 d . . . . .
H32 H 0.618388 0.664167 0.379276 0.075 Uiso 1 1 calc R U . . .
C33 C 0.66997(16) 0.7344(3) 0.43307(10) 0.0748(8) Uani 1 1 d . . . . .
H33 H 0.663904 0.676655 0.452604 0.090 Uiso 1 1 calc R U . . .
C34 C 0.70613(16) 0.8268(3) 0.44854(10) 0.0761(8) Uani 1 1 d . . . . .
C35 C 0.71362(15) 0.9137(3) 0.41875(10) 0.0750(8) Uani 1 1 d . . . . .
H35 H 0.736732 0.977166 0.428825 0.090 Uiso 1 1 calc R U . . .
C36 C 0.68734(13) 0.9065(2) 0.37487(9) 0.0627(7) Uani 1 1 d . . . . .
H36 H 0.693047 0.964169 0.355249 0.075 Uiso 1 1 calc R U . . .
C37 C 0.7375(2) 0.8355(4) 0.49620(12) 0.1141(14) Uani 1 1 d . . . . .
H37A H 0.775373 0.786403 0.500729 0.171 Uiso 1 1 calc R U . . .
H37B H 0.704938 0.815610 0.515962 0.171 Uiso 1 1 calc R U . . .
H37C H 0.752269 0.910126 0.502213 0.171 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 C4 1.721(3) . ?
S1 C1 1.723(3) . ?
O1 C9 1.350(4) . ?
O1 C10 1.446(4) . ?
N1 C2 1.402(4) . ?
N1 S3 1.630(3) . ?
C1 C2 1.381(4) . ?
C1 C9 1.446(4) . ?
S2 C8 1.689(3) . ?
S2 C5 1.702(3) . ?
O2 C9 1.212(4) . ?
C2 C3 1.414(4) . ?
S3 O3 1.417(2) . ?
S3 O4 1.422(2) . ?
S3 C11 1.762(3) . ?
C3 C4 1.362(4) . ?
C4 C5 1.463(4) . ?
C5 C6 1.392(4) . ?
C6 C7 1.428(4) . ?
C7 C8 1.331(5) . ?
C11 C16 1.382(4) . ?
C11 C12 1.382(4) . ?
C12 C13 1.377(4) . ?
C13 C14 1.388(4) . ?
C14 C15 1.389(4) . ?
C14 C17 1.501(4) . ?
C15 C16 1.376(4) . ?
C21 C22 1.377(3) . ?
C21 C29 1.453(3) . ?
C21 S21 1.721(3) . ?
O21 C29 1.333(3) . ?
O21 C30 1.449(3) . ?
N21 C22 1.400(3) . ?
N21 S23 1.627(2) . ?
S21 C24 1.718(2) . ?
C23 C24 1.368(3) . ?
C23 C22 1.413(3) . ?
O23 S23 1.4266(17) . ?
S23 O24 1.4206(19) . ?
S23 C31 1.757(3) . ?
O22 C29 1.214(3) . ?
S22 C28 1.704(3) . ?
S22 C25 1.710(3) . ?
C25 C26 1.381(4) . ?
C25 C24 1.459(3) . ?
C27 C28 1.331(4) . ?
C27 C26 1.421(4) . ?
C31 C32 1.384(3) . ?
C31 C36 1.386(4) . ?
C32 C33 1.378(4) . ?
C33 C34 1.385(5) . ?
C34 C35 1.400(4) . ?
C34 C37 1.509(5) . ?
C35 C36 1.373(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
C4 S1 C1 91.52(15) . . ?
C9 O1 C10 115.9(3) . . ?
C2 N1 S3 127.2(2) . . ?
C2 C1 C9 124.9(3) . . ?
C2 C1 S1 111.2(2) . . ?
C9 C1 S1 123.8(3) . . ?
C8 S2 C5 92.25(17) . . ?
C1 C2 N1 121.4(3) . . ?
C1 C2 C3 112.7(3) . . ?
N1 C2 C3 125.9(3) . . ?
O3 S3 O4 120.71(14) . . ?
O3 S3 N1 108.26(16) . . ?
O4 S3 N1 104.26(15) . . ?
O3 S3 C11 106.98(14) . . ?
O4 S3 C11 108.44(14) . . ?
N1 S3 C11 107.59(14) . . ?
C4 C3 C2 112.5(3) . . ?
C3 C4 C5 127.5(3) . . ?
C3 C4 S1 112.2(2) . . ?
C5 C4 S1 120.4(2) . . ?
C6 C5 C4 128.1(3) . . ?
C6 C5 S2 111.4(2) . . ?
C4 C5 S2 120.5(2) . . ?
C5 C6 C7 110.3(3) . . ?
C8 C7 C6 113.6(3) . . ?
C7 C8 S2 112.5(3) . . ?
O2 C9 O1 122.9(3) . . ?
O2 C9 C1 124.4(3) . . ?
O1 C9 C1 112.7(3) . . ?
C16 C11 C12 119.9(3) . . ?
C16 C11 S3 120.2(2) . . ?
C12 C11 S3 119.9(2) . . ?
C13 C12 C11 119.7(3) . . ?
C12 C13 C14 121.4(3) . . ?
C13 C14 C15 117.9(3) . . ?
C13 C14 C17 121.4(3) . . ?
C15 C14 C17 120.7(3) . . ?
C16 C15 C14 121.3(3) . . ?
C15 C16 C11 119.9(3) . . ?
C22 C21 C29 125.3(2) . . ?
C22 C21 S21 111.55(18) . . ?
C29 C21 S21 123.2(2) . . ?
C29 O21 C30 115.6(2) . . ?
C22 N21 S23 126.72(18) . . ?
C24 S21 C21 91.35(12) . . ?
C24 C23 C22 112.2(2) . . ?
O24 S23 O23 120.58(12) . . ?
O24 S23 N21 104.36(12) . . ?
O23 S23 N21 108.17(11) . . ?
O24 S23 C31 108.48(12) . . ?
O23 S23 C31 107.59(11) . . ?
N21 S23 C31 106.94(12) . . ?
C21 C22 N21 120.9(2) . . ?
C21 C22 C23 112.6(2) . . ?
N21 C22 C23 126.4(2) . . ?
C28 S22 C25 91.71(14) . . ?
C26 C25 C24 128.0(2) . . ?
C26 C25 S22 110.99(19) . . ?
C24 C25 S22 121.01(18) . . ?
C23 C24 C25 128.0(2) . . ?
C23 C24 S21 112.25(18) . . ?
C25 C24 S21 119.77(18) . . ?
C28 C27 C26 112.8(3) . . ?
C25 C26 C27 111.8(3) . . ?
C27 C28 S22 112.7(2) . . ?
O22 C29 O21 124.1(2) . . ?
O22 C29 C21 124.2(2) . . ?
O21 C29 C21 111.7(2) . . ?
C32 C31 C36 120.7(3) . . ?
C32 C31 S23 118.8(2) . . ?
C36 C31 S23 120.48(19) . . ?
C33 C32 C31 119.3(3) . . ?
C32 C33 C34 121.1(3) . . ?
C33 C34 C35 118.5(3) . . ?
C33 C34 C37 121.7(3) . . ?
C35 C34 C37 119.8(3) . . ?
C36 C35 C34 121.0(3) . . ?
C35 C36 C31 119.3(3) . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_MET2
_database_code_depnum_ccdc_archive 'CCDC 2068062'
loop_
_audit_author_name
_audit_author_address
'Christophe Vande Velde'
;University of Antwerp
Belgium
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        'Methyl 4-(2-thienyl)benzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 O2 S'
_chemical_formula_sum            'C12 H10 O2 S'
_chemical_formula_weight         218.26

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   5.968(3)
_cell_length_b                   7.371(3)
_cell_length_c                   24.210(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.51(2)
_cell_angle_gamma                90
_cell_volume                     1061.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12146
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      63.69

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.510
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7475
_exptl_absorpt_correction_T_max  1.417
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Rigaku RAPID II'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11590
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.663
_diffrn_reflns_theta_max         63.693
_diffrn_reflns_theta_full        63.693
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1604
_reflns_number_gt                1535
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    0.977

_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.
;

_computing_data_collection       'CrystalClear 2.0'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²+0.4127P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0041(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.38(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1604
_refine_ls_number_parameters     152
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C2A C 0.4333(7) 0.2526(5) 0.40702(18) 0.0486(11) Uani 0.712(7) 1 d D . P A 1
S1A S 0.2729(4) 0.1682(5) 0.35215(9) 0.0598(7) Uani 0.712(7) 1 d D . P A 1
C5A C 0.4603(19) 0.2349(16) 0.3049(5) 0.060(2) Uani 0.712(7) 1 d D . P A 1
H5A H 0.438196 0.217998 0.266770 0.072 Uiso 0.712(7) 1 calc R U P A 1
C4A C 0.643(2) 0.315(2) 0.3310(5) 0.061(2) Uani 0.712(7) 1 d D . P A 1
H4A H 0.766208 0.357091 0.313375 0.074 Uiso 0.712(7) 1 calc R U P A 1
C23A C 0.622(4) 0.327(4) 0.3904(12) 0.0617(19) Uani 0.712(7) 1 d D . P A 1
H23A H 0.730535 0.381540 0.414728 0.074 Uiso 0.712(7) 1 calc R U P A 1
C2B C 0.4333(7) 0.2526(5) 0.40702(18) 0.0486(11) Uani 0.288(7) 1 d D . P A 2
S1B S 0.662(2) 0.341(2) 0.3866(7) 0.0617(19) Uani 0.288(7) 1 d D . P A 2
C5B C 0.588(7) 0.303(6) 0.3177(11) 0.061(2) Uani 0.288(7) 1 d D . P A 2
H5B H 0.666836 0.345151 0.288647 0.074 Uiso 0.288(7) 1 calc R U P A 2
C4B C 0.398(6) 0.202(5) 0.3118(12) 0.060(2) Uani 0.288(7) 1 d D . P A 2
H4B H 0.339370 0.151696 0.278541 0.072 Uiso 0.288(7) 1 calc R U P A 2
C3B C 0.299(6) 0.183(6) 0.3646(13) 0.0598(7) Uani 0.288(7) 1 d D . P A 2
H3B H 0.159669 0.129579 0.368616 0.072 Uiso 0.288(7) 1 calc R U P A 2
O1 O -0.0294(7) 0.1951(6) 0.63705(16) 0.0771(11) Uani 1 1 d . . . . .
O2 O 0.3022(8) 0.3050(7) 0.67014(19) 0.0918(14) Uani 1 1 d . . . . .
C6 C 0.3676(7) 0.2486(5) 0.46388(18) 0.0461(10) Uani 1 1 d . . . . .
C7 C 0.5081(7) 0.3216(5) 0.5075(2) 0.0517(11) Uani 1 1 d . . . . .
H7 H 0.645070 0.372451 0.499943 0.062 Uiso 1 1 calc R U . . .
C8 C 0.4473(8) 0.3195(6) 0.5614(2) 0.0544(11) Uani 1 1 d . . . . .
H8 H 0.543467 0.367752 0.589752 0.065 Uiso 1 1 calc R U . . .
C9 C 0.2408(7) 0.2448(5) 0.57336(18) 0.0478(10) Uani 1 1 d . . . . .
C10 C 0.1014(8) 0.1714(6) 0.5311(2) 0.0549(12) Uani 1 1 d . . . . .
H10 H -0.035247 0.120519 0.538798 0.066 Uiso 1 1 calc R U . . .
C11 C 0.1638(7) 0.1730(5) 0.4771(2) 0.0502(11) Uani 1 1 d . . . . .
H11 H 0.067910 0.122628 0.449033 0.060 Uiso 1 1 calc R U . . .
C12 C 0.1789(8) 0.2511(7) 0.6319(2) 0.0577(12) Uani 1 1 d . . . . .
C13 C -0.1087(12) 0.2060(9) 0.6920(3) 0.0906(19) Uani 1 1 d . . . . .
H13A H -0.085399 0.326617 0.706321 0.136 Uiso 1 1 calc R U . . .
H13B H -0.027252 0.121113 0.716054 0.136 Uiso 1 1 calc R U . . .
H13C H -0.266129 0.177531 0.690166 0.136 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
C2Aa C23A 1.345(19) . ?
C2Aa C6 1.461(6) . ?
C2Aa S1A 1.694(5) . ?
S1Aa C5A 1.733(9) . ?
C5Aa C4A 1.355(12) . ?
C4Aa C23A 1.45(3) . ?
C2Bb C3B 1.35(3) . ?
C2Bb C6 1.461(6) . ?
C2Bb S1B 1.626(11) . ?
S1Bb C5B 1.71(3) . ?
C5Bb C4B 1.35(2) . ?
C4Bb C3B 1.46(4) . ?
O1 C12 1.325(6) . ?
O1 C13 1.450(7) . ?
O2 C12 1.205(7) . ?
C6 C11 1.398(6) . ?
C6 C7 1.403(7) . ?
C7 C8 1.383(7) . ?
C8 C9 1.401(6) . ?
C9 C10 1.377(6) . ?
C9 C12 1.492(6) . ?
C10 C11 1.388(7) . ?

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
C23Aa C2Aa C6 125.7(13) . . ?
C23Aa C2Aa S1A 110.5(13) . . ?
C6 C2Aa S1A 123.7(3) . . ?
C2Aa S1Aa C5A 93.4(4) . . ?
C4Aa C5Aa S1A 110.7(11) . . ?
C5Aa C4Aa C23A 111.1(14) . . ?
C2Aa C23Aa C4A 114(2) . . ?
C3Bb C2Bb C6 121.3(17) . . ?
C3Bb C2Bb S1B 112.5(14) . . ?
C6 C2Bb S1B 126.1(7) . . ?
C2Bb S1Bb C5B 94.1(14) . . ?
C4Bb C5Bb S1B 110(3) . . ?
C5Bb C4Bb C3B 111(3) . . ?
C2Bb C3Bb C4B 112(3) . . ?
C12 O1 C13 116.5(5) . . ?
C11 C6 C7 117.4(4) . . ?
C11 C6 C2A 121.7(4) . . ?
C7 C6 C2A 120.8(4) . . ?
C11 C6 C2B 121.7(4) . . ?
C7 C6 C2B 120.8(4) . . ?
C8 C7 C6 121.4(4) . . ?
C7 C8 C9 120.0(4) . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 C12 122.5(4) . . ?
C8 C9 C12 118.1(4) . . ?
C9 C10 C11 120.4(4) . . ?
C10 C11 C6 121.4(4) . . ?
O2 C12 O1 123.4(5) . . ?
O2 C12 C9 124.0(5) . . ?
O1 C12 C9 112.6(4) . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_bilalmetbt2
_database_code_depnum_ccdc_archive 'CCDC 2068061'
loop_
_audit_author_name
_audit_author_address
'Christophe Vande Velde'
;University of Antwerp
Belgium
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        methyl-2,2'-bithienyl-5-carboxylate
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 O2 S2'
_chemical_formula_sum            'C10 H8 O2 S2'
_chemical_formula_weight         224.28

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.212(3)
_cell_length_b                   6.0050(10)
_cell_length_c                   23.945(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2043.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    35560
_cell_measurement_theta_min      3.69
_cell_measurement_theta_max      67.68

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    4.483
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6866
_exptl_absorpt_correction_T_max  1.2548
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Rigaku RAPID II'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31423
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.692
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1846
_reflns_number_gt                1707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear 2.0'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0812P)²+0.6150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0050(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1846
_refine_ls_number_parameters     142
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1294
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.36150(4) 0.48494(9) 0.40414(2) 0.0576(3) Uani 1 1 d . . . . .
S1' S 0.41696(8) 0.17181(15) 0.24366(3) 0.0583(3) Uani 0.849(3) 1 d D . P A 1
C3' C 0.3383(8) 0.5281(16) 0.2706(3) 0.0552(19) Uani 0.849(3) 1 d D . P A 1
H3' H 0.311564 0.642588 0.291390 0.066 Uiso 0.849(3) 1 calc R U P A 1
C3'B C 0.403(2) 0.229(4) 0.2463(6) 0.0552(19) Uani 0.151(3) 1 d D . P A 2
H3'B H 0.430362 0.088515 0.247603 0.066 Uiso 0.151(3) 1 calc R U P A 2
S1'B S 0.3298(12) 0.576(3) 0.2749(4) 0.055(2) Uani 0.151(3) 1 d D . P A 2
C2' C 0.37592(13) 0.3445(4) 0.29473(8) 0.0488(5) Uani 1 1 d D . . . .
C2 C 0.38261(14) 0.2863(4) 0.35392(8) 0.0480(5) Uani 1 1 d . . . . .
C3 C 0.40441(17) 0.0846(4) 0.37768(9) 0.0591(6) Uani 1 1 d . . . . .
H3 H 0.418213 -0.042668 0.357143 0.071 Uiso 1 1 calc R U . . .
C4' C 0.34261(19) 0.5334(5) 0.21181(11) 0.0718(7) Uani 1 1 d D . . . .
H4' H 0.320524 0.648694 0.189433 0.086 Uiso 1 1 calc R U . A 1
C4 C 0.40361(18) 0.0912(4) 0.43653(9) 0.0613(6) Uani 1 1 d . . . . .
H4 H 0.416505 -0.031327 0.459005 0.074 Uiso 1 1 calc R U . . .
C5 C 0.38195(16) 0.2961(4) 0.45684(8) 0.0541(5) Uani 1 1 d . . . . .
C5' C 0.38369(19) 0.3455(5) 0.19308(10) 0.0730(7) Uani 1 1 d D . . . .
H5' H 0.392656 0.315396 0.155352 0.088 Uiso 1 1 calc R U . A 1
C6 C 0.37798(16) 0.3613(4) 0.51602(8) 0.0557(5) Uani 1 1 d . . . . .
O6 O 0.38860(16) 0.2362(3) 0.55456(6) 0.0783(5) Uani 1 1 d . . . . .
C7 C 0.3570(2) 0.6639(5) 0.57821(9) 0.0722(7) Uani 1 1 d . . . . .
H7A H 0.412831 0.620911 0.598016 0.108 Uiso 1 1 calc R U . . .
H7B H 0.302795 0.603370 0.596736 0.108 Uiso 1 1 calc R U . . .
H7C H 0.352462 0.823356 0.577404 0.108 Uiso 1 1 calc R U . . .
O7 O 0.36123(13) 0.5798(3) 0.52187(6) 0.0704(5) 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 C2 1.720(2) . ?
S1 C5 1.721(2) . ?
S1'a C5' 1.667(3) . ?
S1'a C2' 1.706(2) . ?
C3'a C2' 1.355(8) . ?
C3'a C4' 1.410(8) . ?
C3'Bb C2' 1.404(17) . ?
C3'Bb C5' 1.479(17) . ?
S1'Bb C4' 1.544(11) . ?
S1'Bb C2' 1.609(12) . ?
C2' C2 1.463(3) . ?
C2 C3 1.373(3) . ?
C3 C4 1.410(3) . ?
C4' C5' 1.347(4) . ?
C4 C5 1.358(3) . ?
C5 C6 1.471(3) . ?
C6 O6 1.200(3) . ?
C6 O7 1.341(3) . ?
C7 O7 1.442(2) . ?

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
C2 S1 C5 91.50(10) . . ?
C5' S1'a C2' 92.50(12) . . ?
C2' C3'a C4' 115.3(6) . . ?
C2' C3'Bb C5' 115.3(13) . . ?
C4' S1'Bb C2' 95.5(7) . . ?
C3'a C2' C2 129.3(4) . . ?
C3'Bb C2' C2 131.6(8) . . ?
C3'Bb C2' S1'B 107.2(8) . . ?
C2 C2' S1'B 121.2(4) . . ?
C3'a C2' S1' 108.9(4) . . ?
C2 C2' S1' 121.81(16) . . ?
C3 C2 C2' 128.80(19) . . ?
C3 C2 S1 111.18(15) . . ?
C2' C2 S1 120.02(16) . . ?
C2 C3 C4 112.8(2) . . ?
C5' C4' C3' 109.4(4) . . ?
C5' C4' S1'B 121.1(5) . . ?
C5 C4 C3 112.6(2) . . ?
C4 C5 C6 126.47(19) . . ?
C4 C5 S1 111.87(16) . . ?
C6 C5 S1 121.63(17) . . ?
C4' C5' C3'B 100.9(7) . . ?
C4' C5' S1' 113.89(18) . . ?
O6 C6 O7 123.7(2) . . ?
O6 C6 C5 124.7(2) . . ?
O7 C6 C5 111.58(17) . . ?
C6 O7 C7 116.61(19) . . ?

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.088


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_asd4
_database_code_depnum_ccdc_archive 'CCDC 2068063'
loop_
_audit_author_name
_audit_author_address
'Christophe Vande Velde'
;University of Antwerp
Belgium
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        "2,2'-bithiophene-5-carboxylic acid"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 O2 S2'
_chemical_formula_sum            'C9 H6 O2 S2'
_chemical_formula_weight         210.26

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.4772(13)
_cell_length_b                   12.4117(8)
_cell_length_c                   7.2775(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.438(7)
_cell_angle_gamma                90
_cell_volume                     1838.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12177
_cell_measurement_theta_min      4.168
_cell_measurement_theta_max      63.658

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    4.945
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6703
_exptl_absorpt_correction_T_max  1.2802
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Rigaku RAPID II'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12177
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.172
_diffrn_reflns_theta_max         63.735
_diffrn_reflns_theta_full        63.735
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             1497
_reflns_number_gt                1402
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear 2.1'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXT 2018 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+0.8051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1497
_refine_ls_number_parameters     128
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.29836(3) 0.45956(4) 0.71576(8) 0.0686(3) Uani 1 1 d . . . . .
C1 C 0.35850(10) 0.38134(17) 0.8316(3) 0.0628(5) Uani 1 1 d . . . . .
C2 C 0.33731(12) 0.27852(18) 0.8518(3) 0.0723(6) Uani 1 1 d . . . . .
H2 H 0.363243 0.224260 0.910041 0.087 Uiso 1 1 calc R U . . .
C3 C 0.27198(12) 0.26350(19) 0.7749(3) 0.0740(6) Uani 1 1 d . . . . .
H3 H 0.250021 0.198059 0.778156 0.089 Uiso 1 1 calc R U . . .
C4 C 0.24377(10) 0.35413(17) 0.6951(3) 0.0615(5) Uani 1 1 d . . . . .
S2 S 0.11701(9) 0.27868(13) 0.6206(3) 0.0905(5) Uani 0.700(3) 1 d D U P A 1
C6 C 0.1548(7) 0.4552(9) 0.5019(17) 0.0720(10) Uani 0.700(3) 1 d D U P A 1
H6 H 0.180160 0.514665 0.478106 0.086 Uiso 0.700(3) 1 calc R U P A 1
C6B C 0.1244(9) 0.2998(15) 0.615(3) 0.0905(5) Uani 0.300(3) 1 d D U P A 2
H6B H 0.125318 0.235593 0.681189 0.109 Uiso 0.300(3) 1 calc R U P A 2
S2B S 0.1550(4) 0.4743(5) 0.4782(9) 0.0720(10) Uani 0.300(3) 1 d D U P A 2
C5 C 0.17759(10) 0.36943(17) 0.6052(3) 0.0646(5) Uani 1 1 d D . . . .
C7 C 0.08361(14) 0.4421(3) 0.4308(4) 0.0914(8) Uani 1 1 d D . . . .
H7 H 0.058335 0.490455 0.355498 0.110 Uiso 1 1 calc R U . A 1
C8 C 0.06289(14) 0.3485(3) 0.4949(4) 0.1020(9) Uani 1 1 d D . . . .
H8 H 0.019704 0.325126 0.468379 0.122 Uiso 1 1 calc R U . A 1
C10 C 0.42121(11) 0.42970(19) 0.8982(3) 0.0693(6) Uani 1 1 d . . . . .
O1 O 0.46490(8) 0.36812(13) 0.9850(3) 0.0849(5) Uani 1 1 d . . . . .
H10 H 0.496058 0.404686 1.029732 0.050(11) Uiso 0.5 1 calc R . P . .
O2 O 0.42982(9) 0.52747(14) 0.8708(3) 0.0919(6) Uani 1 1 d . . . . .
H20 H 0.465924 0.545684 0.921432 0.12(2) Uiso 0.5 1 calc R . P . .


_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 1.714(2) . ?
S1 C4 1.717(2) . ?
C1 C2 1.361(3) . ?
C1 C10 1.451(3) . ?
C2 C3 1.403(4) . ?
C3 C4 1.364(3) . ?
C4 C5 1.450(3) . ?
S2 C8 1.608(4) . ?
S2 C5 1.689(2) . ?
C6 C5 1.355(10) . ?
C6 C7 1.500(13) . ?
C6B C5 1.399(15) . ?
C6B C8 1.571(19) . ?
S2B C7 1.518(8) . ?
S2B C5 1.632(6) . ?
C7 C8 1.339(4) . ?
C10 O2 1.246(3) . ?
C10 O1 1.287(3) . ?

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 92.08(10) . . ?
C2 C1 C10 129.2(2) . . ?
C2 C1 S1 111.35(17) . . ?
C10 C1 S1 119.36(17) . . ?
C1 C2 C3 112.5(2) . . ?
C4 C3 C2 113.5(2) . . ?
C3 C4 C5 129.0(2) . . ?
C3 C4 S1 110.53(17) . . ?
C5 C4 S1 120.42(17) . . ?
C8 S2 C5 93.88(15) . . ?
C5 C6 C7 111.5(8) . . ?
C5 C6B C8 108.3(11) . . ?
C7 S2B C5 97.1(3) . . ?
C6 C5 C4 126.8(6) . . ?
C6B C5 C4 126.1(8) . . ?
C6B C5 S2B 110.4(7) . . ?
C4 C5 S2B 123.4(3) . . ?
C6 C5 S2 110.5(6) . . ?
C4 C5 S2 122.63(18) . . ?
C8 C7 C6 107.9(5) . . ?
C8 C7 S2B 118.9(3) . . ?
C7 C8 C6B 105.2(6) . . ?
C7 C8 S2 116.1(2) . . ?
O2 C10 O1 123.6(2) . . ?
O2 C10 C1 119.0(2) . . ?
O1 C10 C1 117.3(2) . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.066


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_s2nh2
_database_code_depnum_ccdc_archive 'CCDC 2068064'
loop_
_audit_author_name
_audit_author_address
'Christophe Vande Velde'
;University of Antwerp
Belgium
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_s2nh2               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.780 Why?
RESPONSE: Only one 70 image run at one chi setting was managed before the only crystal we could find deteriorated.
;
# Added during the CSD deposition process: Thursday 04 March 2021 07:00 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Z-3-chloro-3-(2-thienyl)-2-propenenitrile '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 Cl N S'
_chemical_formula_sum            'C7 H4 Cl N S'
_chemical_formula_weight         169.62

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'
Cl Cl 0.3639 0.7018 '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'
S S 0.3331 0.5567 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.8020(6)
_cell_length_b                   8.7244(10)
_cell_length_c                   15.0040(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     759.49(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5490
_cell_measurement_theta_min      5.85
_cell_measurement_theta_max      63.46

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    6.328
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7711
_exptl_absorpt_correction_T_max  1.5235
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Rigaku RAPID II'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2252
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.867
_diffrn_reflns_theta_max         71.623
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.739
_diffrn_measured_fraction_theta_full 0.780
_diffrn_reflns_Laue_measured_fraction_max 0.739
_diffrn_reflns_Laue_measured_fraction_full 0.780
_diffrn_reflns_point_group_measured_fraction_max 0.659
_diffrn_reflns_point_group_measured_fraction_full 0.703
_reflns_number_total             980
_reflns_number_gt                918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.483
_reflns_Friedel_fraction_max     0.539
_reflns_Friedel_fraction_full    0.585

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrystalClear 2.0'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXD 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1136P)²+0.3248P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.21(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         980
_refine_ls_number_parameters     109
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1673
_refine_ls_wR_factor_gt          0.1590
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.1555(7) 0.6844(6) 0.6613(4) 0.0688(11) Uani 0.627(7) 1 d D . P A 1
C2 C 1.0075(10) 0.5313(9) 0.6175(4) 0.0571(17) Uani 0.627(7) 1 d D . P A 1
C3 C 0.809(4) 0.580(4) 0.577(2) 0.075(2) Uani 0.627(7) 1 d D . P A 1
H3A H 0.702469 0.513686 0.551519 0.090 Uiso 0.627(7) 1 calc R U P A 1
C4 C 0.781(7) 0.742(3) 0.579(3) 0.069(5) Uani 0.627(7) 1 d D . P A 1
H4 H 0.659930 0.794328 0.551629 0.083 Uiso 0.627(7) 1 calc R U P A 1
C5 C 0.952(9) 0.811(4) 0.626(4) 0.079(6) Uani 0.627(7) 1 d D . P A 1
H5 H 0.958323 0.916244 0.636743 0.094 Uiso 0.627(7) 1 calc R U P A 1
S1B S 0.7574(15) 0.5763(15) 0.5660(9) 0.075(2) Uani 0.373(7) 1 d D . P A 2
C2B C 1.0075(10) 0.5313(9) 0.6175(4) 0.0571(17) Uani 0.373(7) 1 d D . P A 2
C3B C 1.114(6) 0.659(4) 0.650(3) 0.0688(11) Uani 0.373(7) 1 d D . P A 2
H3B H 1.259021 0.657898 0.676468 0.083 Uiso 0.373(7) 1 calc R U P A 2
C4B C 0.981(15) 0.795(6) 0.639(8) 0.079(6) Uani 0.373(7) 1 d D . P A 2
H4B H 1.026940 0.891911 0.657845 0.094 Uiso 0.373(7) 1 calc R U P A 2
C5B C 0.779(12) 0.765(4) 0.597(5) 0.069(5) Uani 0.373(7) 1 d D . P A 2
H5B H 0.665226 0.838239 0.586087 0.083 Uiso 0.373(7) 1 calc R U P A 2
Cl1 Cl 0.9143(5) 0.2372(4) 0.5769(7) 0.0763(14) Uani 0.94(3) 1 d . . P A 1
Cl1B Cl 0.898(8) 0.247(7) 0.613(8) 0.0763(14) Uani 0.06(3) 1 d . . P A 2
N1 N 1.4076(11) 0.0534(12) 0.6836(5) 0.097(2) Uani 1 1 d . . . . .
C8 C 1.3479(11) 0.1748(12) 0.6741(5) 0.072(2) Uani 1 1 d . . . . .
C7 C 1.2815(10) 0.3298(10) 0.6657(4) 0.0635(18) Uani 1 1 d . . . . .
H7 H 1.377757 0.403981 0.690138 0.076 Uiso 1 1 calc R U . . .
C6 C 1.0884(10) 0.3773(9) 0.6248(3) 0.0571(17) 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 C5 1.704(17) . ?
S1 C2 1.718(8) . ?
C2 C3 1.369(18) . ?
C2 C6 1.428(9) . ?
C3 C4 1.43(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.358(16) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
S1B C2B 1.691(8) . ?
S1B C5B 1.72(2) . ?
C2B C3B 1.37(2) . ?
C2B C6 1.428(9) . ?
C3B C4B 1.42(4) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.36(2) . ?
C4B H4B 0.9300 . ?
C5B H5B 0.9300 . ?
Cl1 C6 1.741(8) . ?
Cl1B C6 1.59(5) . ?
N1 C8 1.123(11) . ?
C8 C7 1.412(12) . ?
C7 C6 1.343(8) . ?
C7 H7 0.9300 . ?

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 C2 92.3(13) . . ?
C3 C2 C6 127.1(16) . . ?
C3 C2 S1 110.4(15) . . ?
C6 C2 S1 122.6(4) . . ?
C2 C3 C4 113(3) . . ?
C2 C3 H3A 123.3 . . ?
C4 C3 H3A 123.3 . . ?
C5 C4 C3 111(3) . . ?
C5 C4 H4 124.3 . . ?
C3 C4 H4 124.3 . . ?
C4 C5 S1 112(3) . . ?
C4 C5 H5 123.8 . . ?
S1 C5 H5 123.8 . . ?
C2B S1B C5B 92(2) . . ?
C3B C2B C6 126.4(17) . . ?
C3B C2B S1B 111.2(16) . . ?
C6 C2B S1B 122.4(6) . . ?
C2B C3B C4B 113(3) . . ?
C2B C3B H3B 123.4 . . ?
C4B C3B H3B 123.4 . . ?
C5B C4B C3B 111(5) . . ?
C5B C4B H4B 124.4 . . ?
C3B C4B H4B 124.4 . . ?
C4B C5B S1B 112(4) . . ?
C4B C5B H5B 124.1 . . ?
S1B C5B H5B 124.1 . . ?
N1 C8 C7 177.0(8) . . ?
C6 C7 C8 124.3(7) . . ?
C6 C7 H7 117.8 . . ?
C8 C7 H7 117.8 . . ?
C7 C6 C2 126.8(6) . . ?
C7 C6 C2B 126.8(6) . . ?
C7 C6 Cl1B 114(2) . . ?
C2B C6 Cl1B 115.6(19) . . ?
C7 C6 Cl1 117.2(6) . . ?
C2 C6 Cl1 116.0(4) . . ?

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
C5 S1 C2 C3 0(3) . . . . ?
C5 S1 C2 C6 -180(3) . . . . ?
C6 C2 C3 C4 -178(2) . . . . ?
S1 C2 C3 C4 2(3) . . . . ?
C2 C3 C4 C5 -4(6) . . . . ?
C3 C4 C5 S1 4(7) . . . . ?
C2 S1 C5 C4 -2(5) . . . . ?
C5B S1B C2B C3B -6(4) . . . . ?
C5B S1B C2B C6 174(3) . . . . ?
C6 C2B C3B C4B -175(6) . . . . ?
S1B C2B C3B C4B 5(7) . . . . ?
C2B C3B C4B C5B -1(13) . . . . ?
C3B C4B C5B S1B -3(13) . . . . ?
C2B S1B C5B C4B 5(9) . . . . ?
C8 C7 C6 C2 177.1(6) . . . . ?
C8 C7 C6 C2B 177.1(6) . . . . ?
C8 C7 C6 Cl1B 19(5) . . . . ?
C8 C7 C6 Cl1 -1.6(10) . . . . ?
C3 C2 C6 C7 -178.7(19) . . . . ?
S1 C2 C6 C7 0.9(9) . . . . ?
C3 C2 C6 Cl1 0(2) . . . . ?
S1 C2 C6 Cl1 179.6(5) . . . . ?
C3B C2B C6 C7 1(3) . . . . ?
S1B C2B C6 C7 -178.6(8) . . . . ?
C3B C2B C6 Cl1B 159(6) . . . . ?
S1B C2B C6 Cl1B -20(5) . . . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.063


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
