# Electronic Supplementary Material (ESI) 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_6582-hmq-100k_auto
_database_code_depnum_ccdc_archive 'CCDC 2303390'
loop_
_audit_author_name
_audit_author_address
'Meiqian Hu'
;Guilin University of Technology
China
;
_audit_update_record             
;
2023-10-25 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_audit_creation_date             2023-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        z
_chemical_formula_moiety         'C17 H17 Cl N2 O S'
_chemical_formula_sum            'C17 H18 Cl N2 O S'
_chemical_formula_weight         333.84
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.3567(2)
_cell_length_b                   14.2027(5)
_cell_length_c                   21.0025(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.995(4)
_cell_angle_gamma                90
_cell_volume                     1597.62(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5711
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      29.1170
_cell_measurement_theta_min      1.6780
_shelx_estimated_absorpt_T_max   0.707
_shelx_estimated_absorpt_T_min   0.707
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             700
_exptl_crystal_preparation       1
_exptl_crystal_recrystallization_method 1
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9512
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.115
_diffrn_reflns_theta_min         1.731
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  93.00   0.50    0.33    --   10.68  27.00-101.00  236
  2  ω     19.00  55.00   0.50    0.33    --   10.68 -99.00 -30.00   72
  3  ω     15.00  41.00   0.50    0.33    --   10.68 -99.00  30.00   52
  4  ω    -71.00  -5.00   0.50    0.33    --   10.68 -27.00  96.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1220090000
_diffrn_orient_matrix_UB_12      0.0178698000
_diffrn_orient_matrix_UB_13      -0.0056409000
_diffrn_orient_matrix_UB_21      -0.0221234000
_diffrn_orient_matrix_UB_22      -0.0007437000
_diffrn_orient_matrix_UB_23      0.0331946000
_diffrn_orient_matrix_UB_31      0.0464870000
_diffrn_orient_matrix_UB_32      0.0466301000
_diffrn_orient_matrix_UB_33      0.0026977000
_diffrn_oxdiff_digest_frames     
;
0137f77d6775d7a1a7744287a036ff6d2c00042f91c
;
_diffrn_oxdiff_digest_hkl        
;
01b36f1d223591cf6ddc298117268acedc6826
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2809
_reflns_number_total             3476
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.067
_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)+(0.0402P)²+0.6835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0949
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00D(H00E,H00F), C00H(H00J,H00K), C00L(H00N,H00O)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00D), C00E(H00G), C00F(H00H), C00G(H00I),
 C00I(H00L), C00K(H00M), C00M(H00P)
;
_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
S001 S 0.34148(9) 0.48145(3) 0.71594(2) 0.02119(13) Uani 1 1 d . . . . .
Cl02 Cl 0.05127(11) 0.62209(3) 0.98796(2) 0.03586(16) Uani 1 1 d . . . . .
O003 O 0.8516(2) 0.37664(8) 0.51823(6) 0.0231(3) Uani 1 1 d . . . . .
N004 N 0.4040(3) 0.30762(9) 0.67049(7) 0.0179(3) Uani 1 1 d . . . . .
N005 N 0.5028(3) 0.36335(9) 0.61925(6) 0.0166(3) Uani 1 1 d . . . . .
C006 C 0.2361(3) 0.30323(11) 0.77385(8) 0.0162(4) Uani 1 1 d . . . . .
C007 C 0.3291(3) 0.35599(11) 0.71805(8) 0.0161(3) Uani 1 1 d . . . . .
C008 C 0.2638(3) 0.51836(11) 0.79378(8) 0.0173(4) Uani 1 1 d . . . . .
C009 C 0.3707(3) 0.22565(12) 0.79540(8) 0.0190(4) Uani 1 1 d . . . . .
H009 H 0.517980 0.207157 0.774180 0.023 Uiso 1 1 calc R . . . .
C00A C 0.0168(3) 0.32801(12) 0.80437(8) 0.0189(4) Uani 1 1 d . . . . .
H00A H -0.079122 0.379933 0.789303 0.023 Uiso 1 1 calc R . . . .
C00B C 0.7711(3) 0.37948(12) 0.63157(8) 0.0191(4) Uani 1 1 d . . . . .
H00B H 0.857755 0.318516 0.637786 0.023 Uiso 1 1 calc R . . . .
H00C H 0.794738 0.417489 0.670723 0.023 Uiso 1 1 calc R . . . .
C00C C -0.0619(3) 0.27702(12) 0.85677(8) 0.0215(4) Uani 1 1 d . . . . .
H00D H -0.211347 0.294300 0.877495 0.026 Uiso 1 1 calc R . . . .
C00D C 0.8791(4) 0.43100(12) 0.57517(8) 0.0205(4) Uani 1 1 d . . . . .
H00E H 0.792667 0.492131 0.569537 0.025 Uiso 1 1 calc R . . . .
H00F H 1.058320 0.443826 0.583497 0.025 Uiso 1 1 calc R . . . .
C00E C 0.0599(4) 0.57790(12) 0.80060(9) 0.0218(4) Uani 1 1 d . . . . .
H00G H -0.035489 0.596179 0.764096 0.026 Uiso 1 1 calc R . . . .
C00F C 0.4072(3) 0.49370(12) 0.84698(8) 0.0208(4) Uani 1 1 d . . . . .
H00H H 0.550692 0.455176 0.842359 0.025 Uiso 1 1 calc R . . . .
C00G C -0.0056(4) 0.61084(12) 0.86021(9) 0.0238(4) Uani 1 1 d . . . . .
H00I H -0.144017 0.651950 0.864814 0.029 Uiso 1 1 calc R . . . .
C00H C 0.4760(3) 0.30529(11) 0.56141(8) 0.0190(4) Uani 1 1 d . . . . .
H00J H 0.296924 0.293981 0.551763 0.023 Uiso 1 1 calc R . . . .
H00K H 0.558360 0.243618 0.568193 0.023 Uiso 1 1 calc R . . . .
C00I C 0.2911(4) 0.17494(12) 0.84781(8) 0.0225(4) Uani 1 1 d . . . . .
H00L H 0.384480 0.122043 0.862337 0.027 Uiso 1 1 calc R . . . .
C00J C 0.1340(4) 0.58280(11) 0.91272(8) 0.0228(4) Uani 1 1 d . . . . .
C00K C 0.0768(4) 0.20102(12) 0.87893(8) 0.0224(4) Uani 1 1 d . . . . .
H00M H 0.024746 0.167043 0.915335 0.027 Uiso 1 1 calc R . . . .
C00L C 0.5949(4) 0.35617(12) 0.50625(8) 0.0230(4) Uani 1 1 d . . . . .
H00N H 0.579416 0.316723 0.467525 0.028 Uiso 1 1 calc R . . . .
H00O H 0.503854 0.415727 0.498064 0.028 Uiso 1 1 calc R . . . .
C00M C 0.3407(4) 0.52529(12) 0.90678(9) 0.0247(4) Uani 1 1 d . . . . .
H00P H 0.436334 0.507602 0.943377 0.030 Uiso 1 1 calc R . . . .


_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
S001 C007 1.7837(16) . ?
S001 C008 1.7732(16) . ?
Cl02 C00J 1.7405(17) . ?
O003 C00D 1.429(2) . ?
O003 C00L 1.423(2) . ?
N004 N005 1.4437(18) . ?
N004 C007 1.282(2) . ?
N005 C00B 1.474(2) . ?
N005 C00H 1.473(2) . ?
C006 C007 1.484(2) . ?
C006 C009 1.388(2) . ?
C006 C00A 1.393(2) . ?
C008 C00E 1.391(2) . ?
C008 C00F 1.389(3) . ?
C009 H009 0.9500 . ?
C009 C00I 1.389(2) . ?
C00A H00A 0.9500 . ?
C00A C00C 1.389(2) . ?
C00B H00B 0.9900 . ?
C00B H00C 0.9900 . ?
C00B C00D 1.516(2) . ?
C00C H00D 0.9500 . ?
C00C C00K 1.386(3) . ?
C00D H00E 0.9900 . ?
C00D H00F 0.9900 . ?
C00E H00G 0.9500 . ?
C00E C00G 1.387(2) . ?
C00F H00H 0.9500 . ?
C00F C00M 1.386(2) . ?
C00G H00I 0.9500 . ?
C00G C00J 1.380(3) . ?
C00H H00J 0.9900 . ?
C00H H00K 0.9900 . ?
C00H C00L 1.515(2) . ?
C00I H00L 0.9500 . ?
C00I C00K 1.381(3) . ?
C00J C00M 1.383(3) . ?
C00K H00M 0.9500 . ?
C00L H00N 0.9900 . ?
C00L H00O 0.9900 . ?
C00M H00P 0.9500 . ?

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
C008 S001 C007 105.25(8) . . ?
C00L O003 C00D 110.08(13) . . ?
C007 N004 N005 114.24(13) . . ?
N004 N005 C00B 108.87(13) . . ?
N004 N005 C00H 106.02(12) . . ?
C00H N005 C00B 108.21(13) . . ?
C009 C006 C007 118.59(15) . . ?
C009 C006 C00A 119.19(15) . . ?
C00A C006 C007 122.21(15) . . ?
N004 C007 S001 120.23(12) . . ?
N004 C007 C006 117.28(14) . . ?
C006 C007 S001 122.48(12) . . ?
C00E C008 S001 118.16(14) . . ?
C00F C008 S001 122.11(13) . . ?
C00F C008 C00E 119.64(15) . . ?
C006 C009 H009 119.8 . . ?
C006 C009 C00I 120.35(16) . . ?
C00I C009 H009 119.8 . . ?
C006 C00A H00A 119.9 . . ?
C00C C00A C006 120.20(16) . . ?
C00C C00A H00A 119.9 . . ?
N005 C00B H00B 109.9 . . ?
N005 C00B H00C 109.9 . . ?
N005 C00B C00D 108.79(14) . . ?
H00B C00B H00C 108.3 . . ?
C00D C00B H00B 109.9 . . ?
C00D C00B H00C 109.9 . . ?
C00A C00C H00D 119.9 . . ?
C00K C00C C00A 120.23(17) . . ?
C00K C00C H00D 119.9 . . ?
O003 C00D C00B 110.98(14) . . ?
O003 C00D H00E 109.4 . . ?
O003 C00D H00F 109.4 . . ?
C00B C00D H00E 109.4 . . ?
C00B C00D H00F 109.4 . . ?
H00E C00D H00F 108.0 . . ?
C008 C00E H00G 119.7 . . ?
C00G C00E C008 120.61(17) . . ?
C00G C00E H00G 119.7 . . ?
C008 C00F H00H 120.0 . . ?
C00M C00F C008 120.00(17) . . ?
C00M C00F H00H 120.0 . . ?
C00E C00G H00I 120.6 . . ?
C00J C00G C00E 118.79(17) . . ?
C00J C00G H00I 120.6 . . ?
N005 C00H H00J 109.9 . . ?
N005 C00H H00K 109.9 . . ?
N005 C00H C00L 109.10(14) . . ?
H00J C00H H00K 108.3 . . ?
C00L C00H H00J 109.9 . . ?
C00L C00H H00K 109.9 . . ?
C009 C00I H00L 119.8 . . ?
C00K C00I C009 120.34(17) . . ?
C00K C00I H00L 119.8 . . ?
C00G C00J Cl02 119.32(15) . . ?
C00G C00J C00M 121.46(16) . . ?
C00M C00J Cl02 119.21(15) . . ?
C00C C00K H00M 120.2 . . ?
C00I C00K C00C 119.66(16) . . ?
C00I C00K H00M 120.2 . . ?
O003 C00L C00H 112.33(15) . . ?
O003 C00L H00N 109.1 . . ?
O003 C00L H00O 109.1 . . ?
C00H C00L H00N 109.1 . . ?
C00H C00L H00O 109.1 . . ?
H00N C00L H00O 107.9 . . ?
C00F C00M H00P 120.3 . . ?
C00J C00M C00F 119.43(18) . . ?
C00J C00M H00P 120.3 . . ?

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
S001 C008 C00E C00G -178.40(13) . . . . ?
S001 C008 C00F C00M 179.16(13) . . . . ?
Cl02 C00J C00M C00F 179.89(13) . . . . ?
N004 N005 C00B C00D 175.37(13) . . . . ?
N004 N005 C00H C00L -175.54(14) . . . . ?
N005 N004 C007 S001 2.2(2) . . . . ?
N005 N004 C007 C006 -177.21(14) . . . . ?
N005 C00B C00D O003 -60.73(18) . . . . ?
N005 C00H C00L O003 57.91(18) . . . . ?
C006 C009 C00I C00K 0.2(3) . . . . ?
C006 C00A C00C C00K -0.2(3) . . . . ?
C007 S001 C008 C00E -122.02(14) . . . . ?
C007 S001 C008 C00F 61.38(16) . . . . ?
C007 N004 N005 C00B 87.64(17) . . . . ?
C007 N004 N005 C00H -156.15(15) . . . . ?
C007 C006 C009 C00I 179.42(16) . . . . ?
C007 C006 C00A C00C -179.47(16) . . . . ?
C008 S001 C007 N004 -172.11(14) . . . . ?
C008 S001 C007 C006 7.31(17) . . . . ?
C008 C00E C00G C00J -0.6(3) . . . . ?
C008 C00F C00M C00J -1.2(3) . . . . ?
C009 C006 C007 S001 -135.10(15) . . . . ?
C009 C006 C007 N004 44.3(2) . . . . ?
C009 C006 C00A C00C 1.7(3) . . . . ?
C009 C00I C00K C00C 1.4(3) . . . . ?
C00A C006 C007 S001 46.1(2) . . . . ?
C00A C006 C007 N004 -134.50(18) . . . . ?
C00A C006 C009 C00I -1.7(3) . . . . ?
C00A C00C C00K C00I -1.4(3) . . . . ?
C00B N005 C00H C00L -58.88(17) . . . . ?
C00D O003 C00L C00H -56.93(17) . . . . ?
C00E C008 C00F C00M 2.6(3) . . . . ?
C00E C00G C00J Cl02 -179.01(13) . . . . ?
C00E C00G C00J C00M 2.0(3) . . . . ?
C00F C008 C00E C00G -1.7(3) . . . . ?
C00G C00J C00M C00F -1.1(3) . . . . ?
C00H N005 C00B C00D 60.57(16) . . . . ?
C00L O003 C00D C00B 58.06(18) . . . . ?

_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 1.430
_oxdiff_exptl_absorpt_empirical_full_min 0.624
