# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1872209'
_audit_update_record             
;
2018-10-09 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 Cl I N2 O S'
_chemical_formula_sum            'C22 H14 Cl I N2 O S'
_chemical_formula_weight         516.76

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'
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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   9.8708(4)
_cell_length_b                   40.1183(17)
_cell_length_c                   9.9473(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3939.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3691
_cell_measurement_theta_min      3.5300
_cell_measurement_theta_max      20.0340

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            BROWN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_F_000             2032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.883
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'xcalibur sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56114
_diffrn_reflns_av_unetI/netI     0.1142
_diffrn_reflns_av_R_equivalents  0.1507
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_k_max       55
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         29.542
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5137
_reflns_number_gt                2491
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+11.1346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5137
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1807
_refine_ls_R_factor_gt           0.0766
_refine_ls_wR_factor_ref         0.1766
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.24713(6) 0.69489(2) 0.64391(6) 0.0598(2) Uani 1 1 d . . . . .
S1 S 0.61848(19) 0.62163(4) 0.67937(16) 0.0360(4) Uani 1 1 d . . . . .
Cl1 Cl 0.5528(3) 0.77521(5) 0.9009(2) 0.0637(6) Uani 1 1 d . . . . .
O1 O 0.7735(5) 0.56540(11) 0.6773(5) 0.0433(13) Uani 1 1 d . . . . .
H1A H 0.745092 0.584285 0.663113 0.065 Uiso 1 1 calc R U . . .
N1 N 0.6820(6) 0.57857(13) 0.8812(5) 0.0329(13) Uani 1 1 d . . . . .
N2 N 0.6137(6) 0.62990(13) 0.9533(5) 0.0347(14) Uani 1 1 d . . . . .
C22 C 0.4945(7) 0.63358(17) 0.4019(6) 0.0288(15) Uani 1 1 d . . . . .
H22 H 0.578762 0.642332 0.424455 0.035 Uiso 1 1 calc R U . . .
C8 C 0.6373(7) 0.61113(16) 0.8510(6) 0.0309(15) Uani 1 1 d . . . . .
C15 C 0.5055(7) 0.65644(16) 0.7019(6) 0.0323(16) Uani 1 1 d . . . . .
C16 C 0.4049(7) 0.65986(16) 0.6125(7) 0.0364(16) Uani 1 1 d . . . . .
C17 C 0.3890(8) 0.63996(16) 0.4876(6) 0.0373(17) Uani 1 1 d . . . . .
C6 C 0.7888(7) 0.52464(16) 0.8484(6) 0.0343(16) Uani 1 1 d . . . . .
C14 C 0.5420(6) 0.67800(16) 0.8159(7) 0.0319(16) Uani 1 1 d . . . . .
C9 C 0.5875(7) 0.66364(17) 0.9348(6) 0.0326(16) Uani 1 1 d . . . . .
C7 C 0.7490(7) 0.55752(16) 0.7940(6) 0.0319(15) Uani 1 1 d . . . . .
C1 C 0.9050(8) 0.50989(18) 0.7999(7) 0.0458(19) Uani 1 1 d . . . . .
H1 H 0.957353 0.520789 0.735727 0.055 Uiso 1 1 calc R U . . .
C18 C 0.2635(8) 0.62504(18) 0.4559(8) 0.0456(19) Uani 1 1 d . . . . .
H18 H 0.188115 0.629028 0.509639 0.055 Uiso 1 1 calc R U . . .
C13 C 0.5334(7) 0.71215(16) 0.8070(7) 0.0391(18) Uani 1 1 d . . . . .
H13 H 0.505680 0.722092 0.727149 0.047 Uiso 1 1 calc R U . . .
C12 C 0.5659(7) 0.73167(18) 0.9166(8) 0.0424(19) Uani 1 1 d . . . . .
C21 C 0.4866(9) 0.6162(2) 0.2911(8) 0.056(2) Uani 1 1 d . . . . .
H21 H 0.559146 0.614837 0.231800 0.067 Uiso 1 1 calc R U . . .
C10 C 0.6191(7) 0.68435(18) 1.0449(7) 0.0419(18) Uani 1 1 d . . . . .
H10 H 0.648210 0.674832 1.125105 0.050 Uiso 1 1 calc R U . . .
C20 C 0.3662(10) 0.6000(2) 0.2658(8) 0.058(2) Uani 1 1 d . . . . .
H20 H 0.360980 0.585500 0.193071 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7124(8) 0.50776(19) 0.9430(8) 0.049(2) Uani 1 1 d . . . . .
H5 H 0.633713 0.517364 0.976854 0.059 Uiso 1 1 calc R U . . .
C19 C 0.2527(9) 0.6046(2) 0.3454(8) 0.051(2) Uani 1 1 d . . . . .
H19 H 0.171215 0.594186 0.324665 0.061 Uiso 1 1 calc R U . . .
C3 C 0.8669(10) 0.46262(19) 0.9373(8) 0.059(2) Uani 1 1 d . . . . .
H3 H 0.892630 0.441495 0.966199 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6075(8) 0.71830(18) 1.0354(8) 0.0465(19) Uani 1 1 d . . . . .
H11 H 0.627610 0.731897 1.108401 0.056 Uiso 1 1 calc R U . . .
C2 C 0.9434(9) 0.4792(2) 0.8461(8) 0.062(2) Uani 1 1 d . . . . .
H2 H 1.023035 0.469611 0.814542 0.074 Uiso 1 1 calc R U . . .
C4 C 0.7521(9) 0.47705(18) 0.9866(8) 0.055(2) Uani 1 1 d . . . . .
H4 H 0.700507 0.465861 1.050442 0.066 Uiso 1 1 calc R 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
I1 C16 2.121(7) . ?
S1 C8 1.768(6) . ?
S1 C15 1.801(7) . ?
Cl1 C12 1.759(7) . ?
O1 C7 1.228(7) . ?
O1 H1A 0.8200 . ?
N1 C7 1.379(8) . ?
N1 C8 1.411(8) . ?
N2 C8 1.287(8) . ?
N2 C9 1.391(8) . ?
C22 C21 1.306(10) . ?
C22 C17 1.370(9) . ?
C22 H22 0.9300 . ?
C15 C16 1.340(9) . ?
C15 C14 1.471(9) . ?
C16 C17 1.486(9) . ?
C17 C18 1.412(9) . ?
C6 C1 1.378(9) . ?
C6 C5 1.383(10) . ?
C6 C7 1.479(9) . ?
C14 C13 1.375(9) . ?
C14 C9 1.390(9) . ?
C9 C10 1.410(9) . ?
C1 C2 1.367(10) . ?
C1 H1 0.9300 . ?
C18 C19 1.374(10) . ?
C18 H18 0.9300 . ?
C13 C12 1.381(10) . ?
C13 H13 0.9300 . ?
C12 C11 1.360(10) . ?
C21 C20 1.378(11) . ?
C21 H21 0.9300 . ?
C10 C11 1.370(9) . ?
C10 H10 0.9300 . ?
C20 C19 1.384(11) . ?
C20 H20 0.9300 . ?
C5 C4 1.364(10) . ?
C5 H5 0.9300 . ?
C19 H19 0.9300 . ?
C3 C2 1.355(11) . ?
C3 C4 1.364(11) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C2 H2 0.9300 . ?
C4 H4 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
C8 S1 C15 97.5(3) . . ?
C7 O1 H1A 109.5 . . ?
C7 N1 C8 125.7(5) . . ?
C8 N2 C9 119.9(5) . . ?
C21 C22 C17 125.4(7) . . ?
C21 C22 H22 117.3 . . ?
C17 C22 H22 117.3 . . ?
N2 C8 N1 115.4(5) . . ?
N2 C8 S1 127.2(5) . . ?
N1 C8 S1 117.3(5) . . ?
C16 C15 C14 129.2(6) . . ?
C16 C15 S1 117.1(5) . . ?
C14 C15 S1 113.6(5) . . ?
C15 C16 C17 125.3(6) . . ?
C15 C16 I1 121.0(5) . . ?
C17 C16 I1 113.7(5) . . ?
C22 C17 C18 116.7(6) . . ?
C22 C17 C16 122.7(7) . . ?
C18 C17 C16 120.5(7) . . ?
C1 C6 C5 118.8(7) . . ?
C1 C6 C7 118.4(6) . . ?
C5 C6 C7 122.7(7) . . ?
C13 C14 C9 119.2(6) . . ?
C13 C14 C15 121.4(6) . . ?
C9 C14 C15 119.4(6) . . ?
C14 C9 N2 125.2(6) . . ?
C14 C9 C10 119.2(6) . . ?
N2 C9 C10 115.4(6) . . ?
O1 C7 N1 122.1(6) . . ?
O1 C7 C6 121.6(6) . . ?
N1 C7 C6 116.4(6) . . ?
C2 C1 C6 120.0(7) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C19 C18 C17 119.9(8) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C14 C13 C12 120.0(7) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C11 C12 C13 122.1(7) . . ?
C11 C12 Cl1 119.4(6) . . ?
C13 C12 Cl1 118.4(6) . . ?
C22 C21 C20 117.3(8) . . ?
C22 C21 H21 121.4 . . ?
C20 C21 H21 121.4 . . ?
C11 C10 C9 120.9(7) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C21 C20 C19 122.0(8) . . ?
C21 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C4 C5 C6 120.1(8) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C18 C19 C20 118.3(8) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C2 C3 C4 119.7(7) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C12 C11 C10 118.5(7) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C3 C2 C1 120.9(8) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C5 C4 C3 120.6(8) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?

_refine_diff_density_max         0.995
_refine_diff_density_min         -1.048
_refine_diff_density_rms         0.121

