# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_180124
_database_code_depnum_ccdc_archive 'CCDC 1819563'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 I N S'
_chemical_formula_weight         451.30

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.935(6)
_cell_length_b                   20.797(12)
_cell_length_c                   17.5203(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3620(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7279
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      31.0

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.888
_shelx_estimated_absorpt_T_min   0.254
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 14.6199
_diffrn_reflns_number            31359
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.100
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4148
_reflns_number_gt                3027
_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       CRYSTALCLEAR
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_reduction        CRYSTALCLEAR
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4148
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_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
I2 I 0.48475(4) 0.71085(2) 0.51212(2) 0.06284(19) Uani 1 1 d . . . . .
S3 S 0.74629(12) 0.58822(6) 0.76874(8) 0.0541(3) Uani 1 1 d . . . . .
N4 N 0.4071(3) 0.75768(18) 0.8199(2) 0.0446(8) Uani 1 1 d . . . . .
C10 C 0.4710(4) 0.7253(2) 0.7643(3) 0.0402(9) Uani 1 1 d . . . . .
C11 C 0.4467(4) 0.7348(2) 0.6847(3) 0.0428(9) Uani 1 1 d . . . . .
C12 C 0.5183(4) 0.6958(2) 0.6296(3) 0.0436(10) Uani 1 1 d . . . . .
C13 C 0.5701(4) 0.6783(2) 0.7866(2) 0.0430(9) Uani 1 1 d . . . . .
C14 C 0.6331(4) 0.6423(2) 0.7300(3) 0.0418(9) Uani 1 1 d . . . . .
C15 C 0.6089(4) 0.6494(2) 0.6506(3) 0.0439(10) Uani 1 1 d . . . . .
C16 C 0.3134(4) 0.8017(2) 0.7976(3) 0.0454(10) Uani 1 1 d . . . . .
C17 C 0.2828(4) 0.8150(2) 0.7210(3) 0.0484(10) Uani 1 1 d . . . . .
C18 C 0.6819(5) 0.6078(2) 0.5957(3) 0.0491(10) Uani 1 1 d . . . . .
C19 C 0.6178(5) 0.6618(2) 0.8609(3) 0.0536(12) Uani 1 1 d . . . . .
H1 H 0.587548 0.681399 0.905412 0.064 Uiso 1 1 calc R U . . .
C20 C 0.3519(4) 0.7802(2) 0.6646(3) 0.0479(11) Uani 1 1 d . . . . .
H2 H 0.333594 0.787895 0.613314 0.058 Uiso 1 1 calc R U . . .
C21 C 0.7109(5) 0.6150(2) 0.8598(3) 0.0568(12) Uani 1 1 d . . . . .
H3 H 0.751948 0.598807 0.903456 0.068 Uiso 1 1 calc R U . . .
C22 C 0.1191(5) 0.8955(2) 0.7582(4) 0.0619(14) Uani 1 1 d . . . . .
C23 C 0.2421(5) 0.8368(3) 0.8554(3) 0.0604(13) Uani 1 1 d . . . . .
H4 H 0.259002 0.828734 0.906754 0.073 Uiso 1 1 calc R U . . .
C24 C 0.1828(4) 0.8624(2) 0.7026(3) 0.0563(12) Uani 1 1 d . . . . .
H5 H 0.161722 0.870396 0.651777 0.068 Uiso 1 1 calc R U . . .
C25 C 0.8004(5) 0.6271(3) 0.5630(4) 0.0700(15) Uani 1 1 d . . . . .
H6 H 0.836556 0.666720 0.576482 0.084 Uiso 1 1 calc R U . . .
C26 C 0.1501(5) 0.8817(3) 0.8350(4) 0.0683(15) Uani 1 1 d . . . . .
H7 H 0.105628 0.904328 0.873197 0.082 Uiso 1 1 calc R U . . .
C27 C 0.0141(5) 0.9461(3) 0.7402(5) 0.079(2) Uani 1 1 d . . . . .
H8 H 0.002103 0.948782 0.685886 0.119 Uiso 1 1 calc R U . . .
H9 H 0.043260 0.986973 0.759414 0.119 Uiso 1 1 calc R U . . .
H10 H -0.069719 0.934476 0.763726 0.119 Uiso 1 1 calc R U . . .
C28 C 0.6328(6) 0.5478(3) 0.5773(4) 0.0820(18) Uani 1 1 d . . . . .
H11 H 0.553795 0.532981 0.599595 0.098 Uiso 1 1 calc R U . . .
C29 C 0.8676(7) 0.5895(4) 0.5107(4) 0.088(2) Uani 1 1 d . . . . .
H12 H 0.947335 0.603854 0.488737 0.106 Uiso 1 1 calc R U . . .
C30 C 0.8155(8) 0.5306(4) 0.4913(4) 0.0850(19) Uani 1 1 d . . . . .
H13 H 0.858716 0.505503 0.454851 0.102 Uiso 1 1 calc R U . . .
C31 C 0.7023(9) 0.5091(3) 0.5247(5) 0.097(2) Uani 1 1 d . . . . .
H14 H 0.669853 0.468372 0.512868 0.117 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
I2 C12 2.108(5) . ?
S3 C21 1.726(5) . ?
S3 C14 1.730(4) . ?
N4 C10 1.343(6) . ?
N4 C16 1.363(6) . ?
C10 C11 1.430(7) . ?
C10 C13 1.441(6) . ?
C11 C20 1.380(6) . ?
C11 C12 1.449(7) . ?
C12 C15 1.370(6) . ?
C13 C14 1.392(6) . ?
C13 C19 1.426(6) . ?
C14 C15 1.419(6) . ?
C15 C18 1.484(6) . ?
C16 C17 1.404(7) . ?
C16 C23 1.436(6) . ?
C17 C20 1.403(7) . ?
C17 C24 1.436(6) . ?
C18 C25 1.369(6) . ?
C18 C28 1.377(7) . ?
C19 C21 1.342(7) . ?
C19 H1 0.9300 . ?
C20 H2 0.9300 . ?
C21 H3 0.9300 . ?
C22 C24 1.351(7) . ?
C22 C26 1.409(8) . ?
C22 C27 1.514(7) . ?
C23 C26 1.355(7) . ?
C23 H4 0.9300 . ?
C24 H5 0.9300 . ?
C25 C29 1.377(8) . ?
C25 H6 0.9300 . ?
C26 H7 0.9300 . ?
C27 H8 0.9600 . ?
C27 H9 0.9600 . ?
C27 H10 0.9600 . ?
C28 C31 1.405(8) . ?
C28 H11 0.9300 . ?
C29 C30 1.371(10) . ?
C29 H12 0.9300 . ?
C30 C31 1.344(11) . ?
C30 H13 0.9300 . ?
C31 H14 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
C21 S3 C14 91.2(2) . . ?
C10 N4 C16 116.9(4) . . ?
N4 C10 C11 123.9(4) . . ?
N4 C10 C13 117.8(4) . . ?
C11 C10 C13 118.3(4) . . ?
C20 C11 C10 117.4(4) . . ?
C20 C11 C12 123.3(4) . . ?
C10 C11 C12 119.3(4) . . ?
C15 C12 C11 122.6(4) . . ?
C15 C12 I2 118.1(3) . . ?
C11 C12 I2 119.3(3) . . ?
C14 C13 C19 111.8(4) . . ?
C14 C13 C10 118.6(4) . . ?
C19 C13 C10 129.6(4) . . ?
C13 C14 C15 124.6(4) . . ?
C13 C14 S3 111.2(3) . . ?
C15 C14 S3 124.2(3) . . ?
C12 C15 C14 116.6(4) . . ?
C12 C15 C18 123.9(4) . . ?
C14 C15 C18 119.5(4) . . ?
N4 C16 C17 123.6(4) . . ?
N4 C16 C23 118.5(4) . . ?
C17 C16 C23 117.9(4) . . ?
C20 C17 C16 117.8(4) . . ?
C20 C17 C24 122.2(5) . . ?
C16 C17 C24 119.9(5) . . ?
C25 C18 C28 118.2(5) . . ?
C25 C18 C15 121.4(4) . . ?
C28 C18 C15 120.4(4) . . ?
C21 C19 C13 113.0(5) . . ?
C21 C19 H1 123.5 . . ?
C13 C19 H1 123.5 . . ?
C11 C20 C17 120.4(4) . . ?
C11 C20 H2 119.8 . . ?
C17 C20 H2 119.8 . . ?
C19 C21 S3 112.8(4) . . ?
C19 C21 H3 123.6 . . ?
S3 C21 H3 123.6 . . ?
C24 C22 C26 118.8(5) . . ?
C24 C22 C27 121.7(6) . . ?
C26 C22 C27 119.5(6) . . ?
C26 C23 C16 119.8(5) . . ?
C26 C23 H4 120.1 . . ?
C16 C23 H4 120.1 . . ?
C22 C24 C17 120.8(5) . . ?
C22 C24 H5 119.6 . . ?
C17 C24 H5 119.6 . . ?
C18 C25 C29 121.9(5) . . ?
C18 C25 H6 119.0 . . ?
C29 C25 H6 119.0 . . ?
C23 C26 C22 122.7(5) . . ?
C23 C26 H7 118.6 . . ?
C22 C26 H7 118.6 . . ?
C22 C27 H8 109.5 . . ?
C22 C27 H9 109.5 . . ?
H8 C27 H9 109.5 . . ?
C22 C27 H10 109.5 . . ?
H8 C27 H10 109.5 . . ?
H9 C27 H10 109.5 . . ?
C18 C28 C31 119.9(6) . . ?
C18 C28 H11 120.1 . . ?
C31 C28 H11 120.1 . . ?
C30 C29 C25 119.3(6) . . ?
C30 C29 H12 120.4 . . ?
C25 C29 H12 120.4 . . ?
C31 C30 C29 120.3(6) . . ?
C31 C30 H13 119.8 . . ?
C29 C30 H13 119.8 . . ?
C30 C31 C28 120.4(6) . . ?
C30 C31 H14 119.8 . . ?
C28 C31 H14 119.8 . . ?

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
C16 N4 C10 C11 0.4(6) . . . . ?
C16 N4 C10 C13 -179.7(4) . . . . ?
N4 C10 C11 C20 0.1(6) . . . . ?
C13 C10 C11 C20 -179.8(4) . . . . ?
N4 C10 C11 C12 -178.1(4) . . . . ?
C13 C10 C11 C12 2.1(6) . . . . ?
C20 C11 C12 C15 -177.7(4) . . . . ?
C10 C11 C12 C15 0.3(7) . . . . ?
C20 C11 C12 I2 2.9(6) . . . . ?
C10 C11 C12 I2 -179.1(3) . . . . ?
N4 C10 C13 C14 177.3(4) . . . . ?
C11 C10 C13 C14 -2.9(6) . . . . ?
N4 C10 C13 C19 -3.3(7) . . . . ?
C11 C10 C13 C19 176.6(4) . . . . ?
C19 C13 C14 C15 -178.2(4) . . . . ?
C10 C13 C14 C15 1.4(6) . . . . ?
C19 C13 C14 S3 1.2(5) . . . . ?
C10 C13 C14 S3 -179.2(3) . . . . ?
C21 S3 C14 C13 -1.0(3) . . . . ?
C21 S3 C14 C15 178.4(4) . . . . ?
C11 C12 C15 C14 -1.8(6) . . . . ?
I2 C12 C15 C14 177.5(3) . . . . ?
C11 C12 C15 C18 178.8(4) . . . . ?
I2 C12 C15 C18 -1.8(6) . . . . ?
C13 C14 C15 C12 1.0(6) . . . . ?
S3 C14 C15 C12 -178.3(3) . . . . ?
C13 C14 C15 C18 -179.6(4) . . . . ?
S3 C14 C15 C18 1.1(6) . . . . ?
C10 N4 C16 C17 -0.9(6) . . . . ?
C10 N4 C16 C23 179.4(4) . . . . ?
N4 C16 C17 C20 0.7(7) . . . . ?
C23 C16 C17 C20 -179.5(4) . . . . ?
N4 C16 C17 C24 -179.7(4) . . . . ?
C23 C16 C17 C24 0.0(6) . . . . ?
C12 C15 C18 C25 86.4(6) . . . . ?
C14 C15 C18 C25 -93.0(6) . . . . ?
C12 C15 C18 C28 -94.8(6) . . . . ?
C14 C15 C18 C28 85.9(6) . . . . ?
C14 C13 C19 C21 -0.8(6) . . . . ?
C10 C13 C19 C21 179.7(5) . . . . ?
C10 C11 C20 C17 -0.2(6) . . . . ?
C12 C11 C20 C17 177.8(4) . . . . ?
C16 C17 C20 C11 -0.1(7) . . . . ?
C24 C17 C20 C11 -179.7(4) . . . . ?
C13 C19 C21 S3 0.0(6) . . . . ?
C14 S3 C21 C19 0.6(4) . . . . ?
N4 C16 C23 C26 178.8(4) . . . . ?
C17 C16 C23 C26 -1.0(7) . . . . ?
C26 C22 C24 C17 -1.5(7) . . . . ?
C27 C22 C24 C17 179.6(4) . . . . ?
C20 C17 C24 C22 -179.3(4) . . . . ?
C16 C17 C24 C22 1.2(7) . . . . ?
C28 C18 C25 C29 2.6(10) . . . . ?
C15 C18 C25 C29 -178.6(6) . . . . ?
C16 C23 C26 C22 0.7(8) . . . . ?
C24 C22 C26 C23 0.5(8) . . . . ?
C27 C22 C26 C23 179.5(5) . . . . ?
C25 C18 C28 C31 -1.7(10) . . . . ?
C15 C18 C28 C31 179.5(6) . . . . ?
C18 C25 C29 C30 -0.8(11) . . . . ?
C25 C29 C30 C31 -2.0(13) . . . . ?
C29 C30 C31 C28 2.8(14) . . . . ?
C18 C28 C31 C30 -1.0(13) . . . . ?

_refine_diff_density_max         0.677
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.074

