# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_B21870F0
_database_code_depnum_ccdc_archive 'CCDC 2377588'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2024-08-14 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_B21870F0            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Limited diffraction due to small size crystals and constrained
experimental beamtime.
;
_vrf_PLAT089_B21870F0            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.73 Note  
RESPONSE: Due to dataset truncated to a resolution of 0.93 Angst since 
little signal could be detected beyond this resolution
;
_vrf_PLAT340_B21870F0            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01292 Ang.  
RESPONSE: see above
;
# end Validation Reply Form
_audit_creation_date             2024-08-14
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_chemical_name_common            ?
_chemical_name_systematic        "2,2'-Dinitrodiphenyl sulfide"
_chemical_formula_moiety         'C12 H8 N2 O4 S'
_chemical_formula_sum            'C12 H8 N2 O4 S'
_chemical_formula_weight         276.26
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   7.850(3)
_cell_length_b                   7.9040(16)
_cell_length_c                   19.553(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1213.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1771
_cell_measurement_temperature    293(20)
_cell_measurement_theta_max      25.5390
_cell_measurement_theta_min      2.7960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.134a (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_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platelet
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -3 5 0.0243
-5 -3 -2 0.0475
5 2 2 0.0514
0 0 -1 0.0111
0 0 1 0.0272
1 5 1 0.0251

_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.038


_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'
_diffrn_ambient_temperature      293(2)
_diffrn_reflns_number            9141
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.780
_diffrn_reflns_theta_max         22.463
_diffrn_reflns_theta_full        22.463
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1569
_reflns_number_gt                1358
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.991

_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_cell_refinement       'CrysAlisPro 1.171.43.134a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.134a 64-bit (release 09-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.134a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0755P)²+0.9836P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_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 
;
 Flack x determined using 560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1569
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1460
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.036
_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 0.3305(4) 0.6277(3) 0.49261(13) 0.0690(8) Uani 1 1 d . . . . .
N1 N 0.0866(11) 0.5382(10) 0.6170(5) 0.070(2) Uani 1 1 d . . . . .
O2 O 0.0120(9) 0.6096(12) 0.6634(4) 0.096(3) Uani 1 1 d . . . . .
O1 O 0.0205(9) 0.4912(12) 0.5649(4) 0.102(3) Uani 1 1 d . . . . .
C2 C 0.2708(10) 0.5105(11) 0.6271(5) 0.054(2) Uani 1 1 d . . . . .
C1 C 0.3854(11) 0.5401(11) 0.5735(4) 0.054(2) Uani 1 1 d . . . . .
C5 C 0.6092(14) 0.4612(14) 0.6522(6) 0.073(3) Uani 1 1 d . . . . .
H5 H 0.724480 0.445623 0.661177 0.088 Uiso 1 1 calc R U . . .
O1' O 0.2227(14) 0.7409(11) 0.3735(4) 0.114(3) Uani 1 1 d . . . . .
C1' C 0.2818(11) 0.4446(9) 0.4447(4) 0.047(2) Uani 1 1 d . . . . .
C6' C 0.3189(11) 0.2802(10) 0.4691(4) 0.055(2) Uani 1 1 d . . . . .
H6' H 0.368928 0.266994 0.511904 0.066 Uiso 1 1 calc R U . . .
N1' N 0.1695(13) 0.6138(11) 0.3489(4) 0.074(2) Uani 1 1 d . . . . .
C5' C 0.2826(12) 0.1418(11) 0.4310(4) 0.059(2) Uani 1 1 d . . . . .
H5' H 0.305595 0.035326 0.448936 0.071 Uiso 1 1 calc R U . . .
C3 C 0.3210(12) 0.4617(12) 0.6902(5) 0.066(3) Uani 1 1 d . . . . .
H3 H 0.241653 0.448811 0.725105 0.079 Uiso 1 1 calc R U . . .
C6 C 0.5579(12) 0.5140(12) 0.5893(5) 0.067(3) Uani 1 1 d . . . . .
H6 H 0.639493 0.533323 0.555722 0.081 Uiso 1 1 calc R U . . .
C3' C 0.1771(12) 0.3091(12) 0.3417(4) 0.063(2) Uani 1 1 d . . . . .
H3' H 0.128328 0.319851 0.298593 0.076 Uiso 1 1 calc R U . . .
C4' C 0.2133(13) 0.1531(11) 0.3669(4) 0.064(2) Uani 1 1 d . . . . .
H4' H 0.191439 0.056372 0.341309 0.076 Uiso 1 1 calc R U . . .
O2' O 0.0861(18) 0.6169(11) 0.2969(5) 0.144(4) Uani 1 1 d . . . . .
C2' C 0.2126(11) 0.4522(11) 0.3799(4) 0.051(2) Uani 1 1 d . . . . .
C4 C 0.4914(13) 0.4312(13) 0.7021(6) 0.079(3) Uani 1 1 d . . . . .
H4 H 0.526235 0.389879 0.744329 0.095 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' 1.765(8) . ?
S1 C1 1.779(9) . ?
N1 O1 1.203(11) . ?
N1 O2 1.218(11) . ?
N1 C2 1.476(13) . ?
C2 C3 1.351(13) . ?
C2 C1 1.400(12) . ?
C1 C6 1.404(13) . ?
C5 C6 1.359(14) . ?
C5 C4 1.365(15) . ?
C5 H5 0.9300 . ?
O1' N1' 1.190(11) . ?
C1' C2' 1.379(11) . ?
C1' C6' 1.415(12) . ?
C6' C5' 1.354(12) . ?
C6' H6' 0.9300 . ?
N1' O2' 1.210(12) . ?
N1' C2' 1.454(12) . ?
C5' C4' 1.368(13) . ?
C5' H5' 0.9300 . ?
C3 C4 1.379(14) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C3' C4' 1.358(13) . ?
C3' C2' 1.384(13) . ?
C3' H3' 0.9300 . ?
C4' H4' 0.9300 . ?
C4 H4 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
C1' S1 C1 101.9(4) . . ?
O1 N1 O2 124.5(9) . . ?
O1 N1 C2 119.4(8) . . ?
O2 N1 C2 116.1(8) . . ?
C3 C2 C1 122.9(8) . . ?
C3 C2 N1 116.8(8) . . ?
C1 C2 N1 120.3(8) . . ?
C2 C1 C6 115.5(8) . . ?
C2 C1 S1 125.1(7) . . ?
C6 C1 S1 119.1(7) . . ?
C6 C5 C4 119.9(9) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C2' C1' C6' 115.5(7) . . ?
C2' C1' S1 122.5(6) . . ?
C6' C1' S1 121.9(6) . . ?
C5' C6' C1' 120.8(7) . . ?
C5' C6' H6' 119.6 . . ?
C1' C6' H6' 119.6 . . ?
O1' N1' O2' 120.8(9) . . ?
O1' N1' C2' 119.5(9) . . ?
O2' N1' C2' 119.6(9) . . ?
C6' C5' C4' 122.4(8) . . ?
C6' C5' H5' 118.8 . . ?
C4' C5' H5' 118.8 . . ?
C2 C3 C4 119.1(9) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C6 C1 122.0(9) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
C4' C3' C2' 120.3(8) . . ?
C4' C3' H3' 119.9 . . ?
C2' C3' H3' 119.9 . . ?
C3' C4' C5' 118.3(8) . . ?
C3' C4' H4' 120.8 . . ?
C5' C4' H4' 120.8 . . ?
C1' C2' C3' 122.6(8) . . ?
C1' C2' N1' 120.9(8) . . ?
C3' C2' N1' 116.5(7) . . ?
C5 C4 C3 120.4(10) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C2 C3 -139.4(10) . . . . ?
O2 N1 C2 C3 40.9(12) . . . . ?
O1 N1 C2 C1 42.7(13) . . . . ?
O2 N1 C2 C1 -137.0(9) . . . . ?
C3 C2 C1 C6 0.6(13) . . . . ?
N1 C2 C1 C6 178.4(8) . . . . ?
C3 C2 C1 S1 -172.3(7) . . . . ?
N1 C2 C1 S1 5.4(12) . . . . ?
C1' S1 C1 C2 -90.2(8) . . . . ?
C1' S1 C1 C6 97.1(7) . . . . ?
C1 S1 C1' C2' 172.2(7) . . . . ?
C1 S1 C1' C6' -10.9(8) . . . . ?
C2' C1' C6' C5' -1.9(12) . . . . ?
S1 C1' C6' C5' -179.0(7) . . . . ?
C1' C6' C5' C4' 1.8(14) . . . . ?
C1 C2 C3 C4 -3.3(14) . . . . ?
N1 C2 C3 C4 178.9(9) . . . . ?
C4 C5 C6 C1 0.4(16) . . . . ?
C2 C1 C6 C5 0.9(14) . . . . ?
S1 C1 C6 C5 174.3(8) . . . . ?
C2' C3' C4' C5' 1.0(14) . . . . ?
C6' C5' C4' C3' -1.3(15) . . . . ?
C6' C1' C2' C3' 1.7(12) . . . . ?
S1 C1' C2' C3' 178.8(7) . . . . ?
C6' C1' C2' N1' -179.7(8) . . . . ?
S1 C1' C2' N1' -2.6(11) . . . . ?
C4' C3' C2' C1' -1.3(13) . . . . ?
C4' C3' C2' N1' -180.0(9) . . . . ?
O1' N1' C2' C1' 14.2(14) . . . . ?
O2' N1' C2' C1' -168.9(11) . . . . ?
O1' N1' C2' C3' -167.1(10) . . . . ?
O2' N1' C2' C3' 9.8(15) . . . . ?
C6 C5 C4 C3 -3.1(16) . . . . ?
C2 C3 C4 C5 4.5(15) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.054

