# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_RK-DJ
_database_code_depnum_ccdc_archive 'CCDC 2223830'
loop_
_audit_author_name
_audit_author_address
'Ramesh Kataria'
;Department of Chemistry, Panjab University, Chandigarh
India
;
_audit_update_record             
;
2022-12-02 deposited with the CCDC.	2023-02-02 downloaded from the CCDC.
;
_audit_creation_date             2022-12-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_systematic        Hydrazone
_chemical_formula_moiety         'C17 H14 Cl N5 O S'
_chemical_formula_sum            'C17 H14 Cl N5 O S'
_chemical_formula_weight         370.844
_chemical_oxdiff_formula         'C H N O S Cl'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.5221(5)
_cell_length_b                   15.2245(7)
_cell_length_c                   10.1523(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.553(5)
_cell_angle_gamma                90
_cell_volume                     1715.69(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5388
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1050
_cell_measurement_theta_min      3.3750
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       needle
_exptl_crystal_F_000             765.508
_exptl_crystal_preparation       'Slow evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.9981
_diffrn_reflns_Laue_measured_fraction_max 0.9387
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14897
_diffrn_reflns_point_group_measured_fraction_full 0.9981
_diffrn_reflns_point_group_measured_fraction_max 0.9387
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.37
_diffrn_reflns_theta_min         3.25
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9387
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00 -30.00   0.50   20.26    --   -9.79 -64.00 -85.00   74
  2  ω    -16.00  48.00   0.50   20.26    --   -9.79  64.00  50.00  128
  3  ω    -10.00  31.00   0.50   20.26    --   10.07  64.00  50.00   82
  4  ω    -51.00 -21.00   0.50   20.26    --   10.07 -64.00 -85.00   60
  5  ω    -28.00  -2.00   0.50   20.26    --   -9.79 -57.00-150.00   52
  6  ω     -2.00  74.00   0.50   20.26    --   10.07  38.00  30.00  152
  7  ω     -5.00  67.00   0.50   20.26    --   10.07  57.00-120.00  144
  8  ω      3.00  58.00   0.50   20.26    --   10.07-125.00 -60.00  110
  9  ω    -59.00  22.00   0.50   20.26    --   10.07 -19.00 150.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0386431000
_diffrn_orient_matrix_UB_12      0.0330233000
_diffrn_orient_matrix_UB_13      -0.0136153000
_diffrn_orient_matrix_UB_21      0.0436261000
_diffrn_orient_matrix_UB_22      -0.0106263000
_diffrn_orient_matrix_UB_23      0.0617786000
_diffrn_orient_matrix_UB_31      0.0261799000
_diffrn_orient_matrix_UB_32      -0.0311013000
_diffrn_orient_matrix_UB_33      -0.0354608000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2227
_reflns_number_total             3646
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2837
_refine_diff_density_min         -0.2834
_refine_diff_density_rms         0.0705
_refine_ls_d_res_high            0.7729
_refine_ls_d_res_low             6.2779
_refine_ls_goodness_of_fit_ref   1.0325
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3646
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.0325
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+0.1415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1545
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N14(H14), C6(H6), C5(H5), C2(H2), C10(H10), C3(H3), C21(H21), C22(H22),
 C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S9 S 0.46005(7) 0.55385(4) 0.18483(7) 0.0770(3) Uani 1.000000 .
Cl19 Cl 0.91428(6) 0.73403(5) 0.94356(7) 0.0808(3) Uani 1.000000 .
O18 O 0.56741(14) 0.26386(10) 0.23254(17) 0.0632(5) Uani 1.000000 .
N14 N 0.66968(16) 0.30978(12) 0.44501(18) 0.0554(5) Uani 1.000000 .
H14 H 0.68717(16) 0.35403(12) 0.49941(18) 0.0665(6) Uiso 1.000000 R
N12 N 0.60170(16) 0.47667(12) 0.39275(19) 0.0541(5) Uani 1.000000 .
N7 N 0.57474(19) 0.62967(14) 0.4209(2) 0.0604(5) Uani 1.000000 .
N15 N 0.71523(17) 0.22875(12) 0.4897(2) 0.0544(5) Uani 1.000000 .
C16 C 0.7889(2) 0.22647(15) 0.6093(2) 0.0534(6) Uani 1.000000 .
N25 N 0.8708(2) 0.12971(16) 0.7950(2) 0.0818(7) Uani 1.000000 .
C13 C 0.59808(19) 0.32160(15) 0.3176(2) 0.0521(6) Uani 1.000000 .
C1 C 0.6558(2) 0.64886(15) 0.5467(2) 0.0551(6) Uani 1.000000 .
C20 C 0.8304(2) 0.13787(16) 0.6602(3) 0.0589(6) Uani 1.000000 .
C8 C 0.5551(2) 0.55294(15) 0.3505(2) 0.0539(6) Uani 1.000000 .
C11 C 0.5600(2) 0.41466(15) 0.2915(2) 0.0530(6) Uani 1.000000 .
C6 C 0.6504(2) 0.73273(15) 0.5987(3) 0.0606(6) Uani 1.000000 .
H6 H 0.5928(2) 0.77215(15) 0.5507(3) 0.0727(8) Uiso 1.000000 R
C5 C 0.7284(2) 0.75831(17) 0.7196(3) 0.0642(7) Uani 1.000000 .
H5 H 0.7237(2) 0.81465(17) 0.7531(3) 0.0771(8) Uiso 1.000000 R
C2 C 0.7422(2) 0.59094(16) 0.6206(3) 0.0654(7) Uani 1.000000 .
H2 H 0.7471(2) 0.53438(16) 0.5879(3) 0.0785(8) Uiso 1.000000 R
C4 C 0.8141(2) 0.70024(17) 0.7914(3) 0.0628(6) Uani 1.000000 .
C10 C 0.4849(2) 0.44332(16) 0.1752(3) 0.0692(7) Uani 1.000000 .
H10 H 0.4508(2) 0.40825(16) 0.0998(3) 0.0831(8) Uiso 1.000000 R
C3 C 0.8207(2) 0.61681(17) 0.7419(3) 0.0700(7) Uani 1.000000 .
H3 H 0.8784(2) 0.57773(17) 0.7907(3) 0.0840(8) Uiso 1.000000 R
C17 C 0.8308(2) 0.30442(17) 0.7002(3) 0.0712(7) Uani 1.000000 .
H17a H 0.8575(14) 0.3497(4) 0.6493(5) 0.1069(11) Uiso 1.000000 GR
H17b H 0.7655(5) 0.3262(7) 0.7330(14) 0.1069(11) Uiso 1.000000 GR
H17c H 0.8962(10) 0.2873(3) 0.7764(9) 0.1069(11) Uiso 1.000000 GR
C21 C 0.8239(2) 0.06721(18) 0.5731(3) 0.0805(8) Uani 1.000000 .
H21 H 0.7979(2) 0.07479(18) 0.4788(3) 0.0966(10) Uiso 1.000000 R
C22 C 0.8567(3) -0.0147(2) 0.6284(4) 0.0982(10) Uani 1.000000 .
H22 H 0.8530(3) -0.0633(2) 0.5719(4) 0.1179(12) Uiso 1.000000 R
C23 C 0.8945(3) -0.0236(2) 0.7660(4) 0.0954(10) Uani 1.000000 .
H23 H 0.9159(3) -0.0783(2) 0.8059(4) 0.1145(12) Uiso 1.000000 R
C24 C 0.9004(3) 0.0496(2) 0.8444(4) 0.0989(10) Uani 1.000000 .
H24 H 0.9269(3) 0.0432(2) 0.9388(4) 0.1187(12) Uiso 1.000000 R
H7 H 0.533(2) 0.6766(17) 0.377(2) 0.067(7) Uiso 1.000000 .


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
S9 C8 1.744(2) . ?
S9 C10 1.714(2) . ?
Cl19 C4 1.740(3) . ?
O18 C13 1.217(3) . ?
N14 H14 0.8600 . ?
N14 N15 1.369(2) . ?
N14 C13 1.347(3) . ?
N12 C8 1.303(3) . ?
N12 C11 1.384(3) . ?
N7 C1 1.396(3) . ?
N7 C8 1.356(3) . ?
N7 H7 0.91(3) . ?
N15 C16 1.283(3) . ?
C16 C20 1.477(3) . ?
C16 C17 1.501(3) . ?
N25 C20 1.328(3) . ?
N25 C24 1.327(4) . ?
C13 C11 1.486(3) . ?
C1 C6 1.390(3) . ?
C1 C2 1.390(3) . ?
C20 C21 1.382(4) . ?
C11 C10 1.336(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.369(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.379(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(3) . ?
C4 C3 1.375(3) . ?
C10 H10 0.9300 . ?
C3 H3 0.9300 . ?
C17 H17a 0.9600 . ?
C17 H17b 0.9600 . ?
C17 H17c 0.9600 . ?
C21 H21 0.9300 . ?
C21 C22 1.378(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.354(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.361(5) . ?
C24 H24 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
C10 S9 C8 88.61(12) . . ?
N15 N14 H14 119.33(11) . . ?
C13 N14 H14 119.33(12) . . ?
C13 N14 N15 121.34(18) . . ?
C11 N12 C8 109.45(19) . . ?
C8 N7 C1 129.7(2) . . ?
H7 N7 C1 114.8(15) . . ?
H7 N7 C8 115.4(15) . . ?
C16 N15 N14 115.83(18) . . ?
C20 C16 N15 115.2(2) . . ?
C17 C16 N15 125.6(2) . . ?
C17 C16 C20 119.1(2) . . ?
C24 N25 C20 117.3(3) . . ?
N14 C13 O18 124.9(2) . . ?
C11 C13 O18 123.1(2) . . ?
C11 C13 N14 112.01(19) . . ?
C6 C1 N7 116.9(2) . . ?
C2 C1 N7 124.6(2) . . ?
C2 C1 C6 118.4(2) . . ?
N25 C20 C16 115.9(2) . . ?
C21 C20 C16 122.0(2) . . ?
C21 C20 N25 122.0(2) . . ?
N12 C8 S9 114.93(17) . . ?
N7 C8 S9 118.30(17) . . ?
N7 C8 N12 126.8(2) . . ?
C13 C11 N12 119.4(2) . . ?
C10 C11 N12 116.6(2) . . ?
C10 C11 C13 124.0(2) . . ?
H6 C6 C1 119.44(14) . . ?
C5 C6 C1 121.1(2) . . ?
C5 C6 H6 119.44(15) . . ?
H5 C5 C6 120.12(15) . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.12(15) . . ?
H2 C2 C1 119.81(14) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.81(15) . . ?
C5 C4 Cl19 119.4(2) . . ?
C3 C4 Cl19 120.6(2) . . ?
C3 C4 C5 120.1(2) . . ?
C11 C10 S9 110.43(19) . . ?
H10 C10 S9 124.79(9) . . ?
H10 C10 C11 124.79(15) . . ?
C4 C3 C2 120.3(2) . . ?
H3 C3 C2 119.87(15) . . ?
H3 C3 C4 119.87(15) . . ?
H17a C17 C16 109.5 . . ?
H17b C17 C16 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C16 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H21 C21 C20 120.60(15) . . ?
C22 C21 C20 118.8(3) . . ?
C22 C21 H21 120.6(2) . . ?
H22 C22 C21 120.4(2) . . ?
C23 C22 C21 119.2(3) . . ?
C23 C22 H22 120.4(2) . . ?
H23 C23 C22 120.9(2) . . ?
C24 C23 C22 118.3(3) . . ?
C24 C23 H23 120.9(2) . . ?
C23 C24 N25 124.3(3) . . ?
H24 C24 N25 117.8(2) . . ?
H24 C24 C23 117.8(2) . . ?

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
S9 C8 N12 C11 -0.93(18) . . . . ?
S9 C8 N7 C1 -171.99(16) . . . . ?
S9 C10 C11 N12 -0.1(2) . . . . ?
S9 C10 C11 C13 178.74(14) . . . . ?
Cl19 C4 C5 C6 179.03(19) . . . . ?
Cl19 C4 C3 C2 -179.1(2) . . . . ?
O18 C13 N14 N15 0.2(3) . . . . ?
O18 C13 C11 N12 -178.2(2) . . . . ?
O18 C13 C11 C10 3.0(3) . . . . ?
N14 N15 C16 C20 175.73(19) . . . . ?
N14 N15 C16 C17 -1.9(2) . . . . ?
N14 C13 C11 N12 1.6(2) . . . . ?
N14 C13 C11 C10 -177.1(2) . . . . ?
N12 C8 N7 C1 6.9(3) . . . . ?
N7 C1 C6 C5 -178.2(2) . . . . ?
N7 C1 C2 C3 178.0(2) . . . . ?
N15 C16 C20 N25 -157.6(2) . . . . ?
N15 C16 C20 C21 20.3(3) . . . . ?
C16 C20 N25 C24 175.2(3) . . . . ?
C16 C20 C21 C22 -175.7(3) . . . . ?
N25 C20 C21 C22 2.2(3) . . . . ?
N25 C24 C23 C22 0.4(4) . . . . ?
C1 C6 C5 C4 0.0(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C6 C5 C4 C3 -0.3(3) . . . . ?
C5 C4 C3 C2 0.2(3) . . . . ?
C21 C22 C23 C24 -1.1(4) . . . . ?


_olex2_exptl_crystal_mounting_method 'mounted using loop'
_olex2_submission_original_sample_id L2
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.343
_oxdiff_exptl_absorpt_empirical_full_min 0.714
