# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_aparna_06062023_0m
_database_code_depnum_ccdc_archive 'CCDC 2310611'
loop_
_audit_author_name
_audit_author_address
'Aparna Tyagi'
;Indian Institute of Technology Delhi
India
;
_audit_update_record             
;
2023-11-27 deposited with the CCDC.	2024-01-16 downloaded from the CCDC.
;
_audit_creation_date             2023-11-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 Cl N2 O3 S, 0.5[C2H6SO]'
_chemical_formula_sum            'C14 H13 Cl N2 O3.50 S1.50'
_chemical_formula_weight         348.80
_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'
Cl Cl 0.1484 0.1585 '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      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                   8.3039(6)
_cell_length_b                   10.6015(7)
_cell_length_c                   11.5759(8)
_cell_angle_alpha                74.614(2)
_cell_angle_beta                 70.161(2)
_cell_angle_gamma                87.736(2)
_cell_volume                     922.80(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    305(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6917
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1644 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.9276.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35334
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.289
_diffrn_reflns_theta_min         1.995
_diffrn_ambient_temperature      305.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3418
_reflns_number_total             4527
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.375
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.047(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0896
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1621P)²+1.3109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2702
_refine_ls_wR_factor_ref         0.2880
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed U11: N2(0.0478)
 Fixed U12: N2(-0.004994)
 Fixed U13: N2(-0.006008)
 Fixed U22: N2(0.051014)
 Fixed U23: N2(0.008906)
 Fixed U33: N2(0.04384)
 Fixed Uiso: H2(0.00001)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 0.8624(2) 0.25501(19) 1.12424(14) 0.0898(5) Uani 1 1 d . . . . .
S1 S 0.66639(13) 0.44086(10) 0.71706(9) 0.0461(3) Uani 1 1 d . . . . .
O1 O 0.5566(4) 0.3236(3) 0.7644(3) 0.0621(8) Uani 1 1 d . . . . .
O2 O 0.7431(5) 0.5005(4) 0.5823(3) 0.0690(9) Uani 1 1 d . . . . .
O4 O 0.6265(4) 0.6239(3) 0.9565(3) 0.0499(6) Uani 1 1 d . . . . .
N1 N 0.5433(4) 0.5507(3) 0.7792(3) 0.0445(7) Uani 1 1 d . . . . .
H1 H 0.487(6) 0.514(5) 0.864(5) 0.053 Uiso 1 1 d . U . . .
N2 N 0.6312(5) 0.6686(3) 0.7544(3) 0.054 Uani 1 1 d . . . . .
C1 C 1.0866(6) 0.3709(5) 0.8898(5) 0.0644(12) Uani 1 1 d . . . . .
H1A H 1.171691 0.355835 0.926529 0.077 Uiso 1 1 calc R U . . .
C2 C 0.9179(6) 0.3332(4) 0.9620(4) 0.0545(10) Uani 1 1 d . . . . .
C3 C 0.7888(5) 0.3518(4) 0.9106(4) 0.0478(8) Uani 1 1 d . . . . .
H3 H 0.675989 0.322883 0.960264 0.057 Uiso 1 1 calc R U . . .
C4 C 0.8335(5) 0.4153(4) 0.7820(4) 0.0433(8) Uani 1 1 d . . . . .
C5 C 0.6645(4) 0.6988(4) 0.8500(3) 0.0399(7) Uani 1 1 d . . . . .
C6 C 0.7474(5) 0.8334(4) 0.8204(4) 0.0452(8) Uani 1 1 d . . . . .
C7 C 0.7099(7) 0.8915(5) 0.9190(5) 0.0622(11) Uani 1 1 d . . . . .
H7 H 0.633058 0.850924 0.999475 0.075 Uiso 1 1 calc R U . . .
C8 C 0.9084(8) 1.0702(5) 0.7788(7) 0.0770(15) Uani 1 1 d . . . . .
H8 H 0.965506 1.149173 0.765884 0.092 Uiso 1 1 calc R U . . .
C9 C 0.7912(9) 1.0134(5) 0.8941(7) 0.0821(16) Uani 1 1 d . . . . .
H9 H 0.764227 1.056484 0.958034 0.098 Uiso 1 1 calc R U . . .
C10 C 0.9432(7) 1.0131(5) 0.6819(5) 0.0731(14) Uani 1 1 d . . . . .
H10 H 1.020699 1.055105 0.602214 0.088 Uiso 1 1 calc R U . . .
C11 C 0.8648(6) 0.8928(5) 0.6999(4) 0.0563(10) Uani 1 1 d . . . . .
H11 H 0.889617 0.852919 0.633803 0.068 Uiso 1 1 calc R U . . .
C12 C 1.0012(6) 0.4552(5) 0.7059(5) 0.0607(11) Uani 1 1 d . . . . .
H12 H 1.028152 0.496846 0.619620 0.073 Uiso 1 1 calc R U . . .
C13 C 1.1272(6) 0.4324(6) 0.7596(6) 0.0758(15) Uani 1 1 d . . . . .
H13 H 1.240617 0.458070 0.709128 0.091 Uiso 1 1 calc R U . . .
H2 H 0.672(3) 0.716(2) 0.656(2) 0.000 Uiso 1 1 d . 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
Cl1 C2 1.744(5) . ?
S1 O1 1.438(3) . ?
S1 O2 1.439(3) . ?
S1 N1 1.664(3) . ?
S1 C4 1.771(4) . ?
O4 C5 1.220(4) . ?
N1 H1 0.91(5) . ?
N1 N2 1.384(5) . ?
N2 C5 1.344(5) . ?
N2 H2 1.06(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.376(7) . ?
C1 C13 1.400(8) . ?
C2 C3 1.377(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(6) . ?
C4 C12 1.382(6) . ?
C5 C6 1.512(5) . ?
C6 C7 1.377(6) . ?
C6 C11 1.397(6) . ?
C7 H7 0.9300 . ?
C7 C9 1.396(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.353(9) . ?
C8 C10 1.354(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.388(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.372(7) . ?
C13 H13 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
O1 S1 N1 104.39(19) . . ?
O1 S1 C4 109.19(19) . . ?
O2 S1 O1 121.1(2) . . ?
O2 S1 N1 106.9(2) . . ?
O2 S1 C4 107.5(2) . . ?
N1 S1 C4 106.94(17) . . ?
S1 N1 H1 109(3) . . ?
N2 N1 S1 113.4(3) . . ?
N2 N1 H1 113(3) . . ?
N1 N2 H2 109.9(14) . . ?
C5 N2 N1 118.8(3) . . ?
C5 N2 H2 130.9(14) . . ?
C2 C1 H1A 120.8 . . ?
C2 C1 C13 118.5(4) . . ?
C13 C1 H1A 120.8 . . ?
C1 C2 Cl1 119.8(4) . . ?
C1 C2 C3 122.5(4) . . ?
C3 C2 Cl1 117.7(3) . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.4(4) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 S1 117.1(3) . . ?
C12 C4 S1 120.8(3) . . ?
C12 C4 C3 122.1(4) . . ?
O4 C5 N2 122.5(3) . . ?
O4 C5 C6 120.9(3) . . ?
N2 C5 C6 116.6(3) . . ?
C7 C6 C5 117.2(4) . . ?
C7 C6 C11 121.5(4) . . ?
C11 C6 C5 121.2(4) . . ?
C6 C7 H7 121.2 . . ?
C6 C7 C9 117.7(5) . . ?
C9 C7 H7 121.2 . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C10 120.6(5) . . ?
C10 C8 H8 119.7 . . ?
C7 C9 H9 119.3 . . ?
C8 C9 C7 121.3(5) . . ?
C8 C9 H9 119.3 . . ?
C8 C10 H10 119.6 . . ?
C8 C10 C11 120.9(5) . . ?
C11 C10 H10 119.6 . . ?
C6 C11 H11 121.0 . . ?
C10 C11 C6 118.0(5) . . ?
C10 C11 H11 121.0 . . ?
C4 C12 H12 120.5 . . ?
C13 C12 C4 119.0(5) . . ?
C13 C12 H12 120.5 . . ?
C1 C13 H13 119.7 . . ?
C12 C13 C1 120.6(4) . . ?
C12 C13 H13 119.7 . . ?

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
Cl1 C2 C3 C4 179.3(3) . . . . ?
S1 N1 N2 C5 -107.7(3) . . . . ?
S1 C4 C12 C13 -179.3(4) . . . . ?
O1 S1 N1 N2 174.2(3) . . . . ?
O1 S1 C4 C3 -43.5(4) . . . . ?
O1 S1 C4 C12 135.2(4) . . . . ?
O2 S1 N1 N2 -56.3(3) . . . . ?
O2 S1 C4 C3 -176.6(3) . . . . ?
O2 S1 C4 C12 2.1(4) . . . . ?
O4 C5 C6 C7 -28.8(6) . . . . ?
O4 C5 C6 C11 147.6(4) . . . . ?
N1 S1 C4 C3 68.9(3) . . . . ?
N1 S1 C4 C12 -112.4(4) . . . . ?
N1 N2 C5 O4 3.1(6) . . . . ?
N1 N2 C5 C6 -175.0(3) . . . . ?
N2 C5 C6 C7 149.4(4) . . . . ?
N2 C5 C6 C11 -34.3(5) . . . . ?
C1 C2 C3 C4 -2.3(7) . . . . ?
C2 C1 C13 C12 0.4(9) . . . . ?
C2 C3 C4 S1 -179.2(3) . . . . ?
C2 C3 C4 C12 2.1(6) . . . . ?
C3 C4 C12 C13 -0.7(7) . . . . ?
C4 S1 N1 N2 58.6(3) . . . . ?
C4 C12 C13 C1 -0.6(9) . . . . ?
C5 C6 C7 C9 177.4(5) . . . . ?
C5 C6 C11 C10 -176.3(4) . . . . ?
C6 C7 C9 C8 -2.8(9) . . . . ?
C7 C6 C11 C10 -0.1(7) . . . . ?
C8 C10 C11 C6 0.8(8) . . . . ?
C9 C8 C10 C11 -2.6(10) . . . . ?
C10 C8 C9 C7 3.6(10) . . . . ?
C11 C6 C7 C9 1.1(7) . . . . ?
C13 C1 C2 Cl1 179.5(4) . . . . ?
C13 C1 C2 C3 1.1(8) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.215 -0.392 0.500 295.9 93.1 '1 DMSO'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
