# 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. 
# 
#######################################################################

data_exp_12702
_audit_block_doi                 10.5517/ccdc.csd.cc2fgp9x
_database_code_depnum_ccdc_archive 'CCDC 2248439'
loop_
_audit_author_name
_audit_author_address
'ZXX CCDC'
;GXU
China
;
_audit_update_record             
;
2023-03-14 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2023-03-14
_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        ?
_chemical_formula_moiety         'C18 H13 Cl I N3 S'
_chemical_formula_sum            'C18 H13 Cl I N3 S'
_chemical_formula_weight         465.72
_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'
I I -0.4742 1.8119 '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'
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                   7.9812(9)
_cell_length_b                   19.5103(15)
_cell_length_c                   12.0639(13)
_cell_angle_alpha                90
_cell_angle_beta                 109.106(13)
_cell_angle_gamma                90
_cell_volume                     1775.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4763
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.8650
_cell_measurement_theta_min      4.1630
_shelx_estimated_absorpt_T_max   0.804
_shelx_estimated_absorpt_T_min   0.682
_exptl_absorpt_coefficient_mu    2.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10221
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.430
_diffrn_reflns_theta_min         3.419
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  84.70   0.90    2.00    --   15.81  38.00 -30.00   93
  2  ω     55.00  82.00   0.90    2.00    --   15.81  77.00 -30.00   30
  3  ω      1.00  52.30   0.90    2.00    --  -16.59  38.00   0.00   57
  4  ω     -3.00  59.10   0.90    2.00    --   15.81  38.00-120.00   69
  5  ω    -20.00  20.50   0.90    2.00    --  -16.59 -99.00 -30.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0723081000
_diffrn_orient_matrix_UB_12      -0.0092101000
_diffrn_orient_matrix_UB_13      -0.0501646000
_diffrn_orient_matrix_UB_21      -0.0153067000
_diffrn_orient_matrix_UB_22      0.0350805000
_diffrn_orient_matrix_UB_23      -0.0155738000
_diffrn_orient_matrix_UB_31      0.0582024000
_diffrn_orient_matrix_UB_32      -0.0024769000
_diffrn_orient_matrix_UB_33      -0.0333500000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3324
_reflns_number_total             4139
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         1.041
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0308P)²+2.1021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0989
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C18(H18), C14(H14), C11(H11), C10(H10), C17(H17), C3(H3),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
I1 I 0.59450(4) 0.27544(2) 0.42502(3) 0.04884(12) Uani 1 1 d . . . . .
Cl1 Cl -0.13393(16) 0.16434(6) 0.31662(11) 0.0559(3) Uani 1 1 d . . . . .
S1 S 0.89765(17) 0.55797(6) 0.61784(9) 0.0497(3) Uani 1 1 d . . . . .
N1 N 0.3417(4) 0.36984(17) 0.6446(3) 0.0325(7) Uani 1 1 d . . . . .
N2 N 0.2412(4) 0.26594(17) 0.5349(3) 0.0340(8) Uani 1 1 d . . . . .
C6 C 0.5012(5) 0.3345(2) 0.5328(3) 0.0297(8) Uani 1 1 d . . . . .
C7 C 0.5711(5) 0.39843(19) 0.5844(3) 0.0278(8) Uani 1 1 d . . . . .
C2 C 0.3636(5) 0.3196(2) 0.5707(3) 0.0313(8) Uani 1 1 d . . . . .
C12 C 0.4679(5) 0.4186(2) 0.6534(3) 0.0313(8) Uani 1 1 d . . . . .
N3 N 0.2103(6) 0.2219(2) 0.6127(3) 0.0547(11) Uani 1 1 d . . . . .
C8 C 0.7073(5) 0.4407(2) 0.5769(3) 0.0320(8) Uani 1 1 d . . . . .
H8 H 0.777230 0.428130 0.531873 0.038 Uiso 1 1 calc R . . . .
C5 C 0.1343(5) 0.2542(2) 0.4243(3) 0.0357(9) Uani 1 1 d . . . . .
H5 H 0.131861 0.278265 0.357292 0.043 Uiso 1 1 calc R . . . .
C13 C 1.0652(5) 0.5613(2) 0.7558(3) 0.0328(9) Uani 1 1 d . . . . .
C9 C 0.7360(5) 0.5015(2) 0.6375(3) 0.0358(9) Uani 1 1 d . . . . .
C18 C 1.0783(6) 0.5182(2) 0.8485(4) 0.0396(10) Uani 1 1 d . . . . .
H18 H 0.993180 0.484432 0.841705 0.047 Uiso 1 1 calc R . . . .
C4 C 0.0309(5) 0.2002(2) 0.4306(4) 0.0374(9) Uani 1 1 d . . . . .
C14 C 1.1945(6) 0.6107(2) 0.7681(4) 0.0435(10) Uani 1 1 d . . . . .
H14 H 1.187798 0.639869 0.705852 0.052 Uiso 1 1 calc R . . . .
C11 C 0.4975(6) 0.4805(2) 0.7142(3) 0.0401(10) Uani 1 1 d . . . . .
H11 H 0.429179 0.493424 0.760058 0.048 Uiso 1 1 calc R . . . .
C10 C 0.6295(6) 0.5213(2) 0.7040(3) 0.0417(10) Uani 1 1 d . . . . .
H10 H 0.649850 0.563367 0.742226 0.050 Uiso 1 1 calc R . . . .
C1 C 0.2000(6) 0.3748(3) 0.6944(4) 0.0486(12) Uani 1 1 d . . . . .
H1A H 0.138982 0.417586 0.671744 0.073 Uiso 1 1 calc GR . . . .
H1B H 0.248742 0.372492 0.778336 0.073 Uiso 1 1 calc GR . . . .
H1C H 0.118401 0.337633 0.666032 0.073 Uiso 1 1 calc GR . . . .
C17 C 1.2186(7) 0.5251(3) 0.9518(4) 0.0544(13) Uani 1 1 d . . . . .
H17 H 1.227300 0.495867 1.014244 0.065 Uiso 1 1 calc R . . . .
C3 C 0.0814(7) 0.1826(3) 0.5472(4) 0.0548(13) Uani 1 1 d . . . . .
H3 H 0.030549 0.147056 0.576500 0.066 Uiso 1 1 calc R . . . .
C15 C 1.3312(7) 0.6167(3) 0.8703(5) 0.0573(13) Uani 1 1 d . . . . .
H15 H 1.416858 0.650218 0.877158 0.069 Uiso 1 1 calc R . . . .
C16 C 1.3451(7) 0.5746(3) 0.9633(5) 0.0634(15) Uani 1 1 d . . . . .
H16 H 1.438727 0.579425 1.033180 0.076 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
I1 C6 2.051(4) . ?
Cl1 C4 1.711(4) . ?
S1 C13 1.762(4) . ?
S1 C9 1.771(4) . ?
N1 C2 1.374(5) . ?
N1 C12 1.365(5) . ?
N1 C1 1.446(5) . ?
N2 C2 1.400(5) . ?
N2 N3 1.353(5) . ?
N2 C5 1.347(5) . ?
C6 C7 1.423(5) . ?
C6 C2 1.352(5) . ?
C7 C12 1.406(5) . ?
C7 C8 1.391(5) . ?
C12 C11 1.391(5) . ?
N3 C3 1.318(6) . ?
C8 C9 1.372(5) . ?
C5 C4 1.355(6) . ?
C13 C18 1.376(5) . ?
C13 C14 1.383(6) . ?
C9 C10 1.401(6) . ?
C18 C17 1.383(6) . ?
C4 C3 1.374(6) . ?
C14 C15 1.358(7) . ?
C11 C10 1.358(6) . ?
C17 C16 1.371(7) . ?
C15 C16 1.365(7) . ?

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
C13 S1 C9 104.91(18) . . ?
C2 N1 C1 126.9(4) . . ?
C12 N1 C2 107.5(3) . . ?
C12 N1 C1 125.3(3) . . ?
N3 N2 C2 121.9(3) . . ?
C5 N2 C2 125.8(3) . . ?
C5 N2 N3 112.2(3) . . ?
C7 C6 I1 126.7(3) . . ?
C2 C6 I1 126.6(3) . . ?
C2 C6 C7 106.7(3) . . ?
C12 C7 C6 106.4(3) . . ?
C8 C7 C6 134.0(4) . . ?
C8 C7 C12 119.6(3) . . ?
N1 C2 N2 120.6(3) . . ?
C6 C2 N1 110.8(3) . . ?
C6 C2 N2 128.2(3) . . ?
N1 C12 C7 108.6(3) . . ?
N1 C12 C11 129.7(4) . . ?
C11 C12 C7 121.6(4) . . ?
C3 N3 N2 103.7(4) . . ?
C9 C8 C7 118.4(4) . . ?
N2 C5 C4 106.1(4) . . ?
C18 C13 S1 125.3(3) . . ?
C18 C13 C14 118.9(4) . . ?
C14 C13 S1 115.8(3) . . ?
C8 C9 S1 117.9(3) . . ?
C8 C9 C10 121.1(4) . . ?
C10 C9 S1 120.7(3) . . ?
C13 C18 C17 119.7(4) . . ?
C5 C4 Cl1 126.5(3) . . ?
C5 C4 C3 105.7(4) . . ?
C3 C4 Cl1 127.7(3) . . ?
C15 C14 C13 120.5(4) . . ?
C10 C11 C12 117.6(4) . . ?
C11 C10 C9 121.6(4) . . ?
C16 C17 C18 120.9(5) . . ?
N3 C3 C4 112.2(4) . . ?
C14 C15 C16 121.3(5) . . ?
C15 C16 C17 118.7(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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.505
_oxdiff_exptl_absorpt_empirical_full_min 0.625
