# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1821253'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 I N2 O S'
_chemical_formula_weight         510.37

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6049(17)
_cell_length_b                   11.226(2)
_cell_length_c                   12.391(3)
_cell_angle_alpha                113.15(3)
_cell_angle_beta                 98.39(3)
_cell_angle_gamma                96.47(3)
_cell_volume                     1069.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3605
_cell_measurement_theta_min      1.8274
_cell_measurement_theta_max      27.8585

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    1.612
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7387
_exptl_absorpt_correction_T_max  0.8301
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10248
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3773
_reflns_number_gt                3312
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0640P)²+0.8693P] 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         3773
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.72473(3) 0.68682(3) 0.66593(2) 0.03284(13) Uani 1 1 d . . .
S1 S 0.54859(11) 0.82104(9) 0.36428(8) 0.0213(2) Uani 1 1 d . . .
O1 O 0.4326(4) 0.9553(3) 0.2489(3) 0.0346(7) Uani 1 1 d . . .
N1 N 0.7070(4) 0.6663(3) 0.2009(3) 0.0194(7) Uani 1 1 d . . .
N2 N 0.5544(4) 0.7877(3) 0.1367(3) 0.0196(7) Uani 1 1 d . . .
C1 C 0.6505(4) 0.7808(4) 0.5565(4) 0.0246(8) Uani 1 1 d . . .
H1 H 0.6352 0.8692 0.5942 0.030 Uiso 1 1 calc R . .
C2 C 0.6236(4) 0.7247(4) 0.4382(3) 0.0195(8) Uani 1 1 d . . .
C3 C 0.6462(5) 0.5915(4) 0.3565(3) 0.0225(8) Uani 1 1 d . . .
H3A H 0.5428 0.5396 0.3027 0.027 Uiso 1 1 calc R . .
H3B H 0.6849 0.5439 0.4044 0.027 Uiso 1 1 calc R . .
C4 C 0.7677(4) 0.6066(3) 0.2819(3) 0.0193(8) Uani 1 1 d . . .
H4 H 0.7809 0.5157 0.2299 0.023 Uiso 1 1 calc R . .
C5 C 0.9313(4) 0.6803(4) 0.3604(3) 0.0197(8) Uani 1 1 d . . .
C6 C 1.0261(5) 0.6169(4) 0.4138(4) 0.0259(9) Uani 1 1 d . . .
H6 H 0.9886 0.5278 0.3988 0.031 Uiso 1 1 calc R . .
C7 C 1.1728(5) 0.6815(4) 0.4879(4) 0.0316(10) Uani 1 1 d . . .
H7 H 1.2366 0.6364 0.5223 0.038 Uiso 1 1 calc R . .
C8 C 1.2281(5) 0.8130(5) 0.5124(4) 0.0319(10) Uani 1 1 d . . .
H8 H 1.3280 0.8586 0.5652 0.038 Uiso 1 1 calc R . .
C9 C 1.1364(5) 0.8763(4) 0.4594(4) 0.0301(9) Uani 1 1 d . . .
H9 H 1.1742 0.9653 0.4745 0.036 Uiso 1 1 calc R . .
C10 C 0.9897(5) 0.8107(4) 0.3845(4) 0.0253(9) Uani 1 1 d . . .
H10 H 0.9276 0.8556 0.3487 0.030 Uiso 1 1 calc R . .
C11 C 0.7627(4) 0.6266(4) 0.0894(3) 0.0199(8) Uani 1 1 d . . .
C12 C 0.8715(5) 0.7146(4) 0.0721(4) 0.0280(9) Uani 1 1 d . . .
H12 H 0.9064 0.8025 0.1315 0.034 Uiso 1 1 calc R . .
C13 C 0.9292(5) 0.6727(5) -0.0335(4) 0.0344(10) Uani 1 1 d . . .
H13 H 1.0050 0.7319 -0.0459 0.041 Uiso 1 1 calc R . .
C14 C 0.8767(5) 0.5455(5) -0.1203(4) 0.0315(10) Uani 1 1 d . . .
H14 H 0.9147 0.5177 -0.1930 0.038 Uiso 1 1 calc R . .
C15 C 0.7693(5) 0.4590(4) -0.1013(4) 0.0297(9) Uani 1 1 d . . .
H15 H 0.7349 0.3709 -0.1604 0.036 Uiso 1 1 calc R . .
C16 C 0.7109(5) 0.4991(4) 0.0029(4) 0.0251(9) Uani 1 1 d . . .
H16 H 0.6356 0.4393 0.0150 0.030 Uiso 1 1 calc R . .
C17 C 0.6075(4) 0.7547(3) 0.2241(3) 0.0174(7) Uani 1 1 d . . .
C18 C 0.4562(4) 0.8788(4) 0.1515(4) 0.0214(8) Uani 1 1 d . . .
C19 C 0.3758(4) 0.8796(4) 0.0370(4) 0.0206(8) Uani 1 1 d . . .
C20 C 0.4111(5) 0.8024(4) -0.0731(4) 0.0257(9) Uani 1 1 d . . .
H20 H 0.4901 0.7492 -0.0759 0.031 Uiso 1 1 calc R . .
C21 C 0.3312(5) 0.8033(5) -0.1781(4) 0.0359(10) Uani 1 1 d . . .
H21 H 0.3552 0.7505 -0.2527 0.043 Uiso 1 1 calc R . .
C22 C 0.2149(5) 0.8820(5) -0.1746(4) 0.0367(11) Uani 1 1 d . . .
H22 H 0.1593 0.8820 -0.2467 0.044 Uiso 1 1 calc R . .
C23 C 0.1819(5) 0.9589(4) -0.0664(4) 0.0339(10) Uani 1 1 d . . .
H23 H 0.1042 1.0131 -0.0639 0.041 Uiso 1 1 calc R . .
C24 C 0.2603(5) 0.9586(4) 0.0392(4) 0.0296(9) Uani 1 1 d . . .
H24 H 0.2357 1.0120 0.1134 0.036 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 C1 2.095(4) . ?
S1 C17 1.776(4) . ?
S1 C2 1.786(4) . ?
O1 C18 1.238(5) . ?
N1 C17 1.356(5) . ?
N1 C11 1.447(5) . ?
N1 C4 1.479(5) . ?
N2 C17 1.314(5) . ?
N2 C18 1.373(5) . ?
C1 C2 1.319(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.493(5) . ?
C3 C4 1.530(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(5) . ?
C4 H4 1.0000 . ?
C5 C10 1.390(6) . ?
C5 C6 1.399(5) . ?
C6 C7 1.376(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.381(5) . ?
C11 C12 1.384(6) . ?
C12 C13 1.393(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.488(5) . ?
C19 C20 1.398(6) . ?
C19 C24 1.401(5) . ?
C20 C21 1.385(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.401(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.371(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(6) . ?
C23 H23 0.9500 . ?
C24 H24 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
C17 S1 C2 103.08(17) . . ?
C17 N1 C11 119.0(3) . . ?
C17 N1 C4 125.3(3) . . ?
C11 N1 C4 115.7(3) . . ?
C17 N2 C18 121.5(3) . . ?
C2 C1 I1 123.9(3) . . ?
C2 C1 H1 118.0 . . ?
I1 C1 H1 118.0 . . ?
C1 C2 C3 129.4(4) . . ?
C1 C2 S1 115.6(3) . . ?
C3 C2 S1 115.0(3) . . ?
C2 C3 C4 109.5(3) . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
N1 C4 C5 112.6(3) . . ?
N1 C4 C3 111.2(3) . . ?
C5 C4 C3 111.8(3) . . ?
N1 C4 H4 106.9 . . ?
C5 C4 H4 106.9 . . ?
C3 C4 H4 106.9 . . ?
C10 C5 C6 117.9(4) . . ?
C10 C5 C4 122.7(3) . . ?
C6 C5 C4 119.4(3) . . ?
C7 C6 C5 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 119.4(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 121.2(4) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
C16 C11 C12 120.6(4) . . ?
C16 C11 N1 119.4(4) . . ?
C12 C11 N1 120.0(3) . . ?
C11 C12 C13 119.1(4) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 119.6(4) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
N2 C17 N1 116.6(3) . . ?
N2 C17 S1 121.4(3) . . ?
N1 C17 S1 122.0(3) . . ?
O1 C18 N2 125.4(4) . . ?
O1 C18 C19 120.7(3) . . ?
N2 C18 C19 113.9(3) . . ?
C20 C19 C24 118.9(4) . . ?
C20 C19 C18 121.8(3) . . ?
C24 C19 C18 119.3(4) . . ?
C21 C20 C19 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.2(4) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 119.5(4) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.9(4) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C23 C24 C19 120.2(4) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?

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
I1 C1 C2 C3 -3.7(6) . . . . ?
I1 C1 C2 S1 176.06(18) . . . . ?
C17 S1 C2 C1 155.7(3) . . . . ?
C17 S1 C2 C3 -24.5(3) . . . . ?
C1 C2 C3 C4 -119.2(4) . . . . ?
S1 C2 C3 C4 61.0(4) . . . . ?
C17 N1 C4 C5 -94.9(4) . . . . ?
C11 N1 C4 C5 84.0(4) . . . . ?
C17 N1 C4 C3 31.5(5) . . . . ?
C11 N1 C4 C3 -149.6(3) . . . . ?
C2 C3 C4 N1 -64.7(4) . . . . ?
C2 C3 C4 C5 62.1(4) . . . . ?
N1 C4 C5 C10 21.3(5) . . . . ?
C3 C4 C5 C10 -104.7(4) . . . . ?
N1 C4 C5 C6 -160.6(3) . . . . ?
C3 C4 C5 C6 73.3(4) . . . . ?
C10 C5 C6 C7 -0.1(6) . . . . ?
C4 C5 C6 C7 -178.3(4) . . . . ?
C5 C6 C7 C8 1.2(6) . . . . ?
C6 C7 C8 C9 -1.7(6) . . . . ?
C7 C8 C9 C10 1.2(6) . . . . ?
C8 C9 C10 C5 -0.2(6) . . . . ?
C6 C5 C10 C9 -0.4(6) . . . . ?
C4 C5 C10 C9 177.7(4) . . . . ?
C17 N1 C11 C16 -111.6(4) . . . . ?
C4 N1 C11 C16 69.4(4) . . . . ?
C17 N1 C11 C12 70.8(5) . . . . ?
C4 N1 C11 C12 -108.2(4) . . . . ?
C16 C11 C12 C13 -0.4(6) . . . . ?
N1 C11 C12 C13 177.1(4) . . . . ?
C11 C12 C13 C14 0.8(6) . . . . ?
C12 C13 C14 C15 -1.2(7) . . . . ?
C13 C14 C15 C16 1.3(6) . . . . ?
C14 C15 C16 C11 -0.9(6) . . . . ?
C12 C11 C16 C15 0.5(6) . . . . ?
N1 C11 C16 C15 -177.1(3) . . . . ?
C18 N2 C17 N1 -178.4(3) . . . . ?
C18 N2 C17 S1 2.6(5) . . . . ?
C11 N1 C17 N2 7.2(5) . . . . ?
C4 N1 C17 N2 -173.9(3) . . . . ?
C11 N1 C17 S1 -173.8(3) . . . . ?
C4 N1 C17 S1 5.1(5) . . . . ?
C2 S1 C17 N2 170.3(3) . . . . ?
C2 S1 C17 N1 -8.7(3) . . . . ?
C17 N2 C18 O1 14.4(6) . . . . ?
C17 N2 C18 C19 -165.5(3) . . . . ?
O1 C18 C19 C20 174.3(4) . . . . ?
N2 C18 C19 C20 -5.7(5) . . . . ?
O1 C18 C19 C24 -6.4(6) . . . . ?
N2 C18 C19 C24 173.6(3) . . . . ?
C24 C19 C20 C21 -0.8(6) . . . . ?
C18 C19 C20 C21 178.5(4) . . . . ?
C19 C20 C21 C22 0.2(7) . . . . ?
C20 C21 C22 C23 0.6(7) . . . . ?
C21 C22 C23 C24 -0.9(7) . . . . ?
C22 C23 C24 C19 0.3(6) . . . . ?
C20 C19 C24 C23 0.5(6) . . . . ?
C18 C19 C24 C23 -178.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.788
_refine_diff_density_min         -0.824
_refine_diff_density_rms         0.099
