# Electronic Supplementary Material (ESI) for RSC Medicinal 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_ex-skg-66-2
_database_code_depnum_ccdc_archive 'CCDC 2269969'
loop_
_audit_author_name
_audit_author_address
'Vajja Krishna Rao'
;National Institute of Pharmaceutical Education and Research SAS Nagar Mohali India
India
;
_audit_update_record             
;
2023-06-14 deposited with the CCDC.	2024-01-25 downloaded from the CCDC.
;
_audit_creation_date             2022-05-04
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 Cl N4 O3 S2'
_chemical_formula_sum            'C16 H15 Cl N4 O3 S2'
_chemical_formula_weight         410.89
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   25.8739(6)
_cell_length_b                   9.36039(17)
_cell_length_c                   14.3273(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.120(2)
_cell_angle_gamma                90
_cell_volume                     3460.96(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8244
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1180
_cell_measurement_theta_min      3.4390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13987
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         3.158
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  14.00   0.50   12.00    --   -9.95 103.00 -66.00  104
  2  ω     -9.00  16.00   0.50   12.00    --   10.22-103.00-169.00   50
  3  ω    -58.00  -3.00   0.50   12.00    --   -9.95 125.00  30.00  110
  4  ω    -47.00  -4.00   0.50   12.00    --   -9.95 125.00  60.00   86
  5  ω    -68.00 -10.00   0.50   12.00    --   -9.95 -38.00-180.00  116
  6  ω    -57.00  -5.00   0.50   12.00    --   -9.95 125.00-120.00  104
  7  ω    -23.00  49.00   0.50   12.00    --   -9.95  38.00-180.00  144
  8  ω    -28.00  -3.00   0.50   12.00    --   -9.95 125.00   0.00   50
  9  ω      7.00  78.00   0.50   12.00    --   10.22  19.00  90.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2807
_reflns_number_total             3343
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+1.2171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C3(H3A), C10(H10), C14(H14), C13(H13), C11(H11)
2.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32421(2) 0.80911(5) 0.47012(3) 0.02848(15) Uani 1 1 d . . . . .
S2 S 0.41481(2) 0.62915(5) 0.38708(4) 0.03107(15) Uani 1 1 d . . . . .
Cl1 Cl 0.52705(2) 1.11017(5) 0.36740(4) 0.03992(16) Uani 1 1 d . . . . .
O1 O 0.28206(5) 0.90842(14) 0.46712(10) 0.0386(4) Uani 1 1 d . . . . .
O2 O 0.33874(6) 0.74335(14) 0.55900(9) 0.0402(4) Uani 1 1 d . . . . .
O3 O 0.06740(6) 0.14318(16) 0.34551(11) 0.0470(4) Uani 1 1 d . . . . .
N2 N 0.33924(6) 0.48195(16) 0.31669(11) 0.0296(4) Uani 1 1 d . . . . .
N1 N 0.31079(6) 0.68933(15) 0.39126(11) 0.0294(4) Uani 1 1 d . . . . .
N3 N 0.25595(7) 0.43100(17) 0.36703(12) 0.0369(4) Uani 1 1 d . . . . .
H3 H 0.261189 0.491317 0.411989 0.044 Uiso 1 1 calc R . . . .
N4 N 0.28539(7) 0.32460(19) 0.23720(12) 0.0426(5) Uani 1 1 d . . . . .
H4A H 0.257364 0.275111 0.230647 0.051 Uiso 1 1 calc R . . . .
H4B H 0.308891 0.314539 0.198201 0.051 Uiso 1 1 calc R . . . .
C8 C 0.29239(8) 0.41655(19) 0.30755(13) 0.0288(4) Uani 1 1 d . . . . .
C7 C 0.34722(7) 0.60083(18) 0.36539(13) 0.0267(4) Uani 1 1 d . . . . .
C1 C 0.46908(7) 1.0281(2) 0.39112(13) 0.0281(4) Uani 1 1 d . . . . .
C6 C 0.46527(8) 0.88155(19) 0.38249(13) 0.0287(4) Uani 1 1 d . . . . .
H6 H 0.492845 0.828231 0.362974 0.034 Uiso 1 1 calc R . . . .
C4 C 0.37919(7) 0.89702(19) 0.43407(12) 0.0256(4) Uani 1 1 d . . . . .
C5 C 0.41948(7) 0.81505(19) 0.40350(13) 0.0264(4) Uani 1 1 d . . . . .
C2 C 0.42850(8) 1.11367(19) 0.41724(13) 0.0295(5) Uani 1 1 d . . . . .
C9 C 0.20812(8) 0.3522(2) 0.36123(14) 0.0319(5) Uani 1 1 d . . . . .
C3 C 0.38353(8) 1.04481(19) 0.43872(13) 0.0307(4) Uani 1 1 d . . . . .
H3A H 0.355672 1.098544 0.456617 0.037 Uiso 1 1 calc R . . . .
C10 C 0.16314(8) 0.4188(2) 0.32672(15) 0.0361(5) Uani 1 1 d . . . . .
H10 H 0.163939 0.513040 0.306403 0.043 Uiso 1 1 calc R . . . .
C12 C 0.11556(8) 0.2042(2) 0.35245(14) 0.0341(5) Uani 1 1 d . . . . .
C14 C 0.20688(8) 0.2123(2) 0.39152(15) 0.0362(5) Uani 1 1 d . . . . .
H14 H 0.237294 0.167994 0.414862 0.043 Uiso 1 1 calc R . . . .
C13 C 0.16041(8) 0.1372(2) 0.38733(15) 0.0372(5) Uani 1 1 d . . . . .
H13 H 0.159542 0.042972 0.407766 0.045 Uiso 1 1 calc R . . . .
C11 C 0.11729(8) 0.3449(2) 0.32262(15) 0.0380(5) Uani 1 1 d . . . . .
H11 H 0.086949 0.389756 0.299524 0.046 Uiso 1 1 calc R . . . .
C18 C 0.43328(9) 1.2739(2) 0.42320(16) 0.0429(6) Uani 1 1 d . . . . .
H18A H 0.461288 1.298749 0.467848 0.064 Uiso 1 1 calc GR . . . .
H18B H 0.401567 1.313645 0.442618 0.064 Uiso 1 1 calc GR . . . .
H18C H 0.440031 1.311538 0.362931 0.064 Uiso 1 1 calc GR . . . .
C15 C 0.06404(10) -0.0084(3) 0.35345(18) 0.0541(7) Uani 1 1 d . . . . .
H15A H 0.086417 -0.052392 0.311188 0.081 Uiso 1 1 calc GR . . . .
H15B H 0.028968 -0.038280 0.338073 0.081 Uiso 1 1 calc GR . . . .
H15C H 0.074486 -0.036565 0.416428 0.081 Uiso 1 1 calc GR . . . .


_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 O1 1.4314(14) . ?
S1 O2 1.4398(14) . ?
S1 N1 1.6118(16) . ?
S1 C4 1.7529(19) . ?
S2 C7 1.774(2) . ?
S2 C5 1.7590(18) . ?
Cl1 C1 1.7403(19) . ?
O3 C12 1.368(2) . ?
O3 C15 1.427(3) . ?
N2 C8 1.356(2) . ?
N2 C7 1.322(2) . ?
N1 C7 1.328(2) . ?
N3 H3 0.8600 . ?
N3 C8 1.322(2) . ?
N3 C9 1.438(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C8 1.328(2) . ?
C1 C6 1.380(2) . ?
C1 C2 1.393(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.390(3) . ?
C4 C5 1.390(3) . ?
C4 C3 1.389(2) . ?
C2 C3 1.384(3) . ?
C2 C18 1.507(3) . ?
C9 C10 1.380(3) . ?
C9 C14 1.381(3) . ?
C3 H3A 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.371(3) . ?
C12 C13 1.381(3) . ?
C12 C11 1.386(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.390(3) . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 O2 117.01(8) . . ?
O1 S1 N1 107.77(9) . . ?
O1 S1 C4 108.61(8) . . ?
O2 S1 N1 110.61(8) . . ?
O2 S1 C4 107.18(9) . . ?
N1 S1 C4 104.98(8) . . ?
C5 S2 C7 103.22(9) . . ?
C12 O3 C15 118.03(17) . . ?
C7 N2 C8 122.40(16) . . ?
C7 N1 S1 120.54(14) . . ?
C8 N3 H3 117.9 . . ?
C8 N3 C9 124.10(16) . . ?
C9 N3 H3 117.9 . . ?
H4A N4 H4B 120.0 . . ?
C8 N4 H4A 120.0 . . ?
C8 N4 H4B 120.0 . . ?
N3 C8 N2 124.42(17) . . ?
N3 C8 N4 119.39(18) . . ?
N4 C8 N2 115.99(17) . . ?
N2 C7 S2 109.45(13) . . ?
N2 C7 N1 125.84(17) . . ?
N1 C7 S2 124.66(14) . . ?
C6 C1 Cl1 118.58(15) . . ?
C6 C1 C2 123.05(17) . . ?
C2 C1 Cl1 118.37(14) . . ?
C1 C6 H6 120.6 . . ?
C1 C6 C5 118.82(17) . . ?
C5 C6 H6 120.6 . . ?
C5 C4 S1 118.46(13) . . ?
C3 C4 S1 121.19(15) . . ?
C3 C4 C5 120.32(17) . . ?
C6 C5 S2 117.74(14) . . ?
C4 C5 S2 122.83(14) . . ?
C4 C5 C6 119.41(17) . . ?
C1 C2 C18 121.83(17) . . ?
C3 C2 C1 116.98(17) . . ?
C3 C2 C18 121.19(18) . . ?
C10 C9 N3 119.27(18) . . ?
C10 C9 C14 120.19(19) . . ?
C14 C9 N3 120.53(19) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 C4 121.30(18) . . ?
C2 C3 H3A 119.4 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.50(19) . . ?
C11 C10 H10 120.2 . . ?
O3 C12 C13 125.03(19) . . ?
O3 C12 C11 115.08(19) . . ?
C13 C12 C11 119.89(19) . . ?
C9 C14 H14 119.8 . . ?
C9 C14 C13 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C12 C13 C14 119.19(19) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
