# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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 
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data_cu_dwj215_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1868183'
_audit_update_record             
;
2018-09-16 deposited with the CCDC.
2019-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 F6 I2 N O5 P S2'
_chemical_formula_weight         905.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   15.0002(8)
_cell_length_b                   8.6636(5)
_cell_length_c                   25.9025(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.518(3)
_cell_angle_gamma                90
_cell_volume                     3286.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2254
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      65.60

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    17.326
_shelx_estimated_absorpt_T_min   0.195
_shelx_estimated_absorpt_T_max   0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5144
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21649
_diffrn_reflns_av_unetI/netI     0.0977
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.142
_diffrn_reflns_theta_max         66.712
_diffrn_reflns_theta_full        66.712
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5781
_reflns_number_gt                3788
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0451P)²+23.3013P] 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         5781
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1654
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
I1 I 0.78122(5) 1.11969(9) 0.36461(2) 0.0520(2) Uani 1 1 d . . . . .
I2 I 0.12925(5) 0.39447(9) 0.47305(2) 0.0495(2) Uani 1 1 d . . . . .
S1 S 0.89853(16) 1.1152(3) 0.62582(8) 0.0374(5) Uani 1 1 d . . . . .
S2 S 0.36679(16) 0.3972(3) 0.72012(8) 0.0373(5) Uani 1 1 d . . . . .
P1 P 0.3882(2) 0.2370(3) 0.35102(13) 0.0553(7) Uani 1 1 d . . . . .
O1 O 0.9889(5) 1.1775(9) 0.6398(3) 0.0517(19) Uani 1 1 d . . . . .
O2 O 0.8258(5) 1.1918(10) 0.6439(2) 0.057(2) Uani 1 1 d . . . . .
O3 O 0.4569(5) 0.3354(8) 0.7226(2) 0.0436(16) Uani 1 1 d . . . . .
O4 O 0.3089(5) 0.3241(9) 0.7507(2) 0.0482(18) Uani 1 1 d . . . . .
F1 F 0.4676(10) 0.1540(11) 0.3331(6) 0.152(6) Uani 1 1 d . . . . .
F2 F 0.3601(15) 0.0996(16) 0.3765(12) 0.273(14) Uani 1 1 d . . . . .
F3 F 0.3069(7) 0.3202(12) 0.3656(8) 0.185(7) Uani 1 1 d . . . . .
F4 F 0.4280(11) 0.3812(12) 0.3403(11) 0.269(14) Uani 1 1 d . . . . .
F5 F 0.4445(15) 0.251(5) 0.4012(6) 0.332(17) Uani 1 1 d . . . . .
F6 F 0.3321(15) 0.184(5) 0.3055(7) 0.37(2) Uani 1 1 d . . . . .
N1 N 0.3895(5) 0.7337(9) 0.3598(2) 0.0291(16) Uani 1 1 d . . . . .
C1 C 0.4815(6) 0.7543(11) 0.4632(3) 0.032(2) Uani 1 1 d . . . . .
H1B H 0.5134 0.7620 0.4991 0.039 Uiso 1 1 calc R U . . .
C2 C 0.5159(6) 0.8245(10) 0.4231(3) 0.0271(18) Uani 1 1 d . . . . .
C3 C 0.4694(6) 0.8132(11) 0.3719(3) 0.0303(19) Uani 1 1 d . . . . .
H3B H 0.4929 0.8609 0.3446 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3564(6) 0.6640(11) 0.3976(3) 0.0315(19) Uani 1 1 d . . . . .
H4B H 0.3013 0.6067 0.3881 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4000(6) 0.6731(11) 0.4500(3) 0.0284(18) Uani 1 1 d . . . . .
C6 C 0.3397(7) 0.7227(12) 0.3038(3) 0.037(2) Uani 1 1 d . . . . .
H6A H 0.3731 0.7799 0.2814 0.056 Uiso 1 1 calc R U . . .
H6B H 0.3346 0.6141 0.2930 0.056 Uiso 1 1 calc R U . . .
H6C H 0.2785 0.7669 0.3001 0.056 Uiso 1 1 calc R U . . .
C7 C 0.6005(7) 0.9101(12) 0.4369(3) 0.036(2) Uani 1 1 d . . . . .
C8 C 0.6718(7) 0.9736(12) 0.4530(3) 0.036(2) Uani 1 1 d . . . . .
C9 C 0.7572(6) 1.0421(11) 0.4767(3) 0.032(2) Uani 1 1 d . . . . .
C10 C 0.7844(6) 1.0439(10) 0.5319(3) 0.032(2) Uani 1 1 d . . . . .
H10A H 0.7454 1.0024 0.5528 0.039 Uiso 1 1 calc R U . . .
C11 C 0.8672(6) 1.1053(11) 0.5557(3) 0.035(2) Uani 1 1 d . . . . .
C12 C 0.9223(7) 1.1738(17) 0.5268(4) 0.061(3) Uani 1 1 d . . . . .
H12A H 0.9784 1.2197 0.5439 0.074 Uiso 1 1 calc R U . . .
C13 C 0.8953(8) 1.1753(16) 0.4722(4) 0.061(3) Uani 1 1 d . . . . .
H13A H 0.9337 1.2221 0.4519 0.074 Uiso 1 1 calc R U . . .
C14 C 0.8143(6) 1.1107(12) 0.4468(3) 0.037(2) Uani 1 1 d . . . . .
C15 C 0.9007(9) 0.9231(12) 0.6470(4) 0.058(3) Uani 1 1 d . . . . .
H15A H 0.8390 0.8798 0.6375 0.087 Uiso 1 1 calc R U . . .
H15B H 0.9416 0.8631 0.6299 0.087 Uiso 1 1 calc R U . . .
H15C H 0.9228 0.9189 0.6854 0.087 Uiso 1 1 calc R U . . .
C16 C 0.3624(6) 0.5997(11) 0.4895(3) 0.034(2) Uani 1 1 d . . . . .
C17 C 0.3300(6) 0.5387(11) 0.5225(3) 0.034(2) Uani 1 1 d . . . . .
C18 C 0.2919(6) 0.4677(10) 0.5625(3) 0.032(2) Uani 1 1 d . . . . .
C19 C 0.3431(6) 0.4662(11) 0.6146(3) 0.0305(19) Uani 1 1 d . . . . .
H19A H 0.4019 0.5125 0.6233 0.037 Uiso 1 1 calc R U . . .
C20 C 0.3060(6) 0.3952(11) 0.6536(3) 0.033(2) Uani 1 1 d . . . . .
C21 C 0.2240(8) 0.3265(17) 0.6422(4) 0.066(4) Uani 1 1 d . . . . .
H21A H 0.1997 0.2809 0.6695 0.079 Uiso 1 1 calc R U . . .
C22 C 0.1745(8) 0.3223(17) 0.5897(4) 0.067(4) Uani 1 1 d . . . . .
H22A H 0.1175 0.2700 0.5812 0.081 Uiso 1 1 calc R U . . .
C23 C 0.2082(6) 0.3934(13) 0.5509(3) 0.042(2) Uani 1 1 d . . . . .
C24 C 0.3802(7) 0.5920(12) 0.7376(3) 0.046(3) Uani 1 1 d . . . . .
H24A H 0.3202 0.6383 0.7364 0.068 Uiso 1 1 calc R U . . .
H24B H 0.4178 0.6011 0.7735 0.068 Uiso 1 1 calc R U . . .
H24C H 0.4102 0.6459 0.7127 0.068 Uiso 1 1 calc R U . . .
O1S O -0.0044(6) 0.4098(10) 0.3676(3) 0.067(2) Uani 1 1 d . . . . .
C1S C 0.0061(9) 0.4543(13) 0.3248(5) 0.056(3) Uani 1 1 d . . . . .
C2S C 0.0969(10) 0.4639(16) 0.3121(5) 0.071(4) Uani 1 1 d . . . . .
H2SA H 0.0907 0.5023 0.2759 0.107 Uiso 1 1 calc R U . . .
H2SB H 0.1355 0.5346 0.3368 0.107 Uiso 1 1 calc R U . . .
H2SC H 0.1249 0.3612 0.3151 0.107 Uiso 1 1 calc R U . . .
C3S C -0.0740(11) 0.5069(14) 0.2842(6) 0.082(5) Uani 1 1 d . . . . .
H3SA H -0.0539 0.5388 0.2523 0.124 Uiso 1 1 calc R U . . .
H3SB H -0.1180 0.4222 0.2756 0.124 Uiso 1 1 calc R U . . .
H3SC H -0.1030 0.5944 0.2981 0.124 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 C14 2.081(8) . ?
I2 C23 2.105(8) . ?
S1 O1 1.431(8) . ?
S1 O2 1.440(8) . ?
S1 C15 1.750(11) . ?
S1 C11 1.776(8) . ?
S2 O3 1.442(7) . ?
S2 O4 1.442(7) . ?
S2 C24 1.748(11) . ?
S2 C20 1.767(8) . ?
P1 F6 1.372(14) . ?
P1 F5 1.393(14) . ?
P1 F4 1.437(11) . ?
P1 F2 1.466(13) . ?
P1 F3 1.533(11) . ?
P1 F1 1.546(10) . ?
N1 C4 1.336(11) . ?
N1 C3 1.359(11) . ?
N1 C6 1.484(10) . ?
C1 C5 1.387(12) . ?
C1 C2 1.395(12) . ?
C1 H1B 0.9500 . ?
C2 C3 1.363(11) . ?
C2 C7 1.447(13) . ?
C3 H3B 0.9500 . ?
C4 C5 1.373(11) . ?
C4 H4B 0.9500 . ?
C5 C16 1.423(12) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.194(13) . ?
C8 C9 1.425(13) . ?
C9 C10 1.398(12) . ?
C9 C14 1.405(12) . ?
C10 C11 1.369(13) . ?
C10 H10A 0.9500 . ?
C11 C12 1.366(14) . ?
C12 C13 1.384(15) . ?
C12 H12A 0.9500 . ?
C13 C14 1.370(14) . ?
C13 H13A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.193(12) . ?
C17 C18 1.426(12) . ?
C18 C23 1.386(13) . ?
C18 C19 1.401(12) . ?
C19 C20 1.396(12) . ?
C19 H19A 0.9500 . ?
C20 C21 1.340(14) . ?
C21 C22 1.400(14) . ?
C21 H21A 0.9500 . ?
C22 C23 1.366(14) . ?
C22 H22A 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O1S C1S 1.216(15) . ?
C1S C2S 1.470(19) . ?
C1S C3S 1.487(16) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
C3S H3SA 0.9800 . ?
C3S H3SB 0.9800 . ?
C3S H3SC 0.9800 . ?

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
O1 S1 O2 119.1(5) . . ?
O1 S1 C15 109.1(5) . . ?
O2 S1 C15 107.5(6) . . ?
O1 S1 C11 107.7(4) . . ?
O2 S1 C11 107.7(4) . . ?
C15 S1 C11 104.9(5) . . ?
O3 S2 O4 118.9(4) . . ?
O3 S2 C24 107.0(5) . . ?
O4 S2 C24 109.3(5) . . ?
O3 S2 C20 108.7(4) . . ?
O4 S2 C20 106.6(4) . . ?
C24 S2 C20 105.6(4) . . ?
F6 P1 F5 165(2) . . ?
F6 P1 F4 109.1(19) . . ?
F5 P1 F4 85.0(16) . . ?
F6 P1 F2 86.1(18) . . ?
F5 P1 F2 80.0(16) . . ?
F4 P1 F2 164.7(17) . . ?
F6 P1 F3 89.8(13) . . ?
F5 P1 F3 94.8(12) . . ?
F4 P1 F3 91.4(7) . . ?
F2 P1 F3 87.1(7) . . ?
F6 P1 F1 87.5(12) . . ?
F5 P1 F1 88.3(12) . . ?
F4 P1 F1 88.2(7) . . ?
F2 P1 F1 94.2(6) . . ?
F3 P1 F1 176.9(10) . . ?
C4 N1 C3 120.7(7) . . ?
C4 N1 C6 120.0(7) . . ?
C3 N1 C6 119.3(7) . . ?
C5 C1 C2 119.0(7) . . ?
C5 C1 H1B 120.5 . . ?
C2 C1 H1B 120.5 . . ?
C3 C2 C1 120.1(8) . . ?
C3 C2 C7 120.8(8) . . ?
C1 C2 C7 119.1(7) . . ?
N1 C3 C2 119.9(8) . . ?
N1 C3 H3B 120.0 . . ?
C2 C3 H3B 120.0 . . ?
N1 C4 C5 121.7(8) . . ?
N1 C4 H4B 119.2 . . ?
C5 C4 H4B 119.2 . . ?
C4 C5 C1 118.6(8) . . ?
C4 C5 C16 120.5(8) . . ?
C1 C5 C16 120.9(7) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C2 173.5(9) . . ?
C7 C8 C9 174.7(9) . . ?
C10 C9 C14 118.7(8) . . ?
C10 C9 C8 118.8(8) . . ?
C14 C9 C8 122.5(7) . . ?
C11 C10 C9 120.1(8) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C12 C11 C10 121.3(8) . . ?
C12 C11 S1 118.8(7) . . ?
C10 C11 S1 119.6(7) . . ?
C11 C12 C13 119.1(9) . . ?
C11 C12 H12A 120.4 . . ?
C13 C12 H12A 120.4 . . ?
C14 C13 C12 121.3(10) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C13 C14 C9 119.4(8) . . ?
C13 C14 I1 117.8(7) . . ?
C9 C14 I1 122.8(6) . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C5 179.4(10) . . ?
C16 C17 C18 179.1(10) . . ?
C23 C18 C19 119.2(8) . . ?
C23 C18 C17 122.0(8) . . ?
C19 C18 C17 118.8(8) . . ?
C20 C19 C18 118.6(8) . . ?
C20 C19 H19A 120.7 . . ?
C18 C19 H19A 120.7 . . ?
C21 C20 C19 121.8(8) . . ?
C21 C20 S2 118.3(7) . . ?
C19 C20 S2 119.9(7) . . ?
C20 C21 C22 119.6(9) . . ?
C20 C21 H21A 120.2 . . ?
C22 C21 H21A 120.2 . . ?
C23 C22 C21 120.0(10) . . ?
C23 C22 H22A 120.0 . . ?
C21 C22 H22A 120.0 . . ?
C22 C23 C18 120.7(8) . . ?
C22 C23 I2 119.1(7) . . ?
C18 C23 I2 120.1(6) . . ?
S2 C24 H24A 109.5 . . ?
S2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O1S C1S C2S 122.1(11) . . ?
O1S C1S C3S 119.8(13) . . ?
C2S C1S C3S 118.1(13) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1S C3S H3SA 109.5 . . ?
C1S C3S H3SB 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
C1S C3S H3SC 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?

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
C5 C1 C2 C3 0.2(14) . . . . ?
C5 C1 C2 C7 179.6(9) . . . . ?
C4 N1 C3 C2 -1.0(13) . . . . ?
C6 N1 C3 C2 179.9(8) . . . . ?
C1 C2 C3 N1 0.1(13) . . . . ?
C7 C2 C3 N1 -179.3(8) . . . . ?
C3 N1 C4 C5 1.7(13) . . . . ?
C6 N1 C4 C5 -179.2(8) . . . . ?
N1 C4 C5 C1 -1.4(14) . . . . ?
N1 C4 C5 C16 179.0(9) . . . . ?
C2 C1 C5 C4 0.4(13) . . . . ?
C2 C1 C5 C16 180.0(9) . . . . ?
C14 C9 C10 C11 -2.9(14) . . . . ?
C8 C9 C10 C11 178.3(9) . . . . ?
C9 C10 C11 C12 3.8(16) . . . . ?
C9 C10 C11 S1 177.0(7) . . . . ?
O1 S1 C11 C12 -9.1(11) . . . . ?
O2 S1 C11 C12 120.5(10) . . . . ?
C15 S1 C11 C12 -125.2(10) . . . . ?
O1 S1 C11 C10 177.6(8) . . . . ?
O2 S1 C11 C10 -52.8(9) . . . . ?
C15 S1 C11 C10 61.4(10) . . . . ?
C10 C11 C12 C13 -2.6(19) . . . . ?
S1 C11 C12 C13 -175.8(10) . . . . ?
C11 C12 C13 C14 0(2) . . . . ?
C12 C13 C14 C9 0(2) . . . . ?
C12 C13 C14 I1 -179.9(11) . . . . ?
C10 C9 C14 C13 0.9(16) . . . . ?
C8 C9 C14 C13 179.6(11) . . . . ?
C10 C9 C14 I1 -178.9(7) . . . . ?
C8 C9 C14 I1 -0.2(14) . . . . ?
C23 C18 C19 C20 -2.7(14) . . . . ?
C17 C18 C19 C20 -179.4(9) . . . . ?
C18 C19 C20 C21 1.3(16) . . . . ?
C18 C19 C20 S2 -177.7(7) . . . . ?
O3 S2 C20 C21 126.8(10) . . . . ?
O4 S2 C20 C21 -2.5(11) . . . . ?
C24 S2 C20 C21 -118.7(10) . . . . ?
O3 S2 C20 C19 -54.1(9) . . . . ?
O4 S2 C20 C19 176.6(8) . . . . ?
C24 S2 C20 C19 60.4(9) . . . . ?
C19 C20 C21 C22 1(2) . . . . ?
S2 C20 C21 C22 -179.6(11) . . . . ?
C20 C21 C22 C23 -3(2) . . . . ?
C21 C22 C23 C18 1(2) . . . . ?
C21 C22 C23 I2 -177.0(11) . . . . ?
C19 C18 C23 C22 1.5(16) . . . . ?
C17 C18 C23 C22 178.1(11) . . . . ?
C19 C18 C23 I2 179.7(7) . . . . ?
C17 C18 C23 I2 -3.8(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3B O3 0.95 2.66 3.168(10) 114.3 3_666
C3 H3B F1 0.95 2.58 3.117(13) 116.5 1_565
C4 H4B F3 0.95 2.56 3.138(14) 119.8 .
C6 H6B F4 0.98 2.61 3.295(16) 127.4 .
C6 H6C O2 0.98 2.38 3.162(12) 136.5 3_676
C13 H13A I2 0.95 3.23 3.986(11) 137.8 1_665
C15 H15B O1S 0.98 2.54 3.337(15) 138.3 3_666
C24 H24A O4 0.98 2.59 3.543(13) 162.9 2_556
C24 H24B O1 0.98 2.47 3.432(10) 169.0 2_646
C2S H2SB O2 0.98 2.47 3.312(17) 144.4 3_676
C3S H3SB O4 0.98 2.42 3.377(15) 164.7 4_565

_refine_diff_density_max         1.529
_refine_diff_density_min         -1.029
_refine_diff_density_rms         0.143



####################################################################### 
# 
# 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_cu_dwjr237_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1868184'
_audit_update_record             
;
2018-09-16 deposited with the CCDC.
2019-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Cl I2 N O5 S2'
_chemical_formula_weight         755.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   5.057(3)
_cell_length_b                   15.197(9)
_cell_length_c                   17.789(11)
_cell_angle_alpha                79.501(15)
_cell_angle_beta                 89.107(15)
_cell_angle_gamma                85.63(2)
_cell_volume                     1340.3(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1410
_cell_measurement_theta_min      5.051
_cell_measurement_theta_max      130.062

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    21.106
_shelx_estimated_absorpt_T_min   0.486
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4651
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14065
_diffrn_reflns_av_unetI/netI     0.1422
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.526
_diffrn_reflns_theta_max         67.081
_diffrn_reflns_theta_full        67.081
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             4611
_reflns_number_gt                3119
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+4.1267P] 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         4611
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.1913
_refine_ls_wR_factor_gt          0.1670
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_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 -0.09489(18) 0.56642(5) 0.59288(5) 0.0514(3) Uani 1 1 d . . . . .
I2 I 0.99428(16) 0.95397(5) 0.82920(5) 0.0452(3) Uani 1 1 d . . . . .
S1 S -0.7840(6) 0.2342(2) 0.76524(17) 0.0411(7) Uani 1 1 d . . . . .
S2 S 1.3237(6) 0.8125(2) 0.50814(18) 0.0482(8) Uani 1 1 d . . . . .
Cl1 Cl 0.5000 0.5000 0.0000 0.0639(14) Uani 1 2 d S . P . .
Cl2 Cl 1.0000 1.0000 0.0000 0.0716(15) Uani 1 2 d S . P . .
O1 O -0.9434(17) 0.2638(6) 0.8233(6) 0.053(2) Uani 1 1 d . . . . .
O2 O -0.908(2) 0.1964(7) 0.7092(6) 0.064(3) Uani 1 1 d . . . . .
O3 O 1.5964(18) 0.8293(9) 0.4984(6) 0.072(3) Uani 1 1 d . . . . .
O4 O 1.254(2) 0.7225(7) 0.5183(6) 0.068(3) Uani 1 1 d . . . . .
N1 N 0.1217(18) 0.6796(7) 0.9423(6) 0.039(2) Uani 1 1 d . . . . .
C1 C 0.3114(19) 0.7255(7) 0.9027(7) 0.033(2) Uani 1 1 d . . . . .
H1B H 0.3953 0.7689 0.9242 0.039 Uiso 1 1 calc R U . . .
C2 C 0.3841(19) 0.7101(7) 0.8319(6) 0.029(2) Uani 1 1 d . . . . .
C3 C 0.259(2) 0.6449(7) 0.7997(7) 0.033(2) Uani 1 1 d . . . . .
H3B H 0.3107 0.6323 0.7509 0.040 Uiso 1 1 calc R U . . .
C4 C 0.061(2) 0.6000(7) 0.8417(7) 0.034(2) Uani 1 1 d . . . . .
C5 C 0.003(2) 0.6176(7) 0.9136(6) 0.034(2) Uani 1 1 d . . . . .
H5A H -0.1261 0.5846 0.9437 0.041 Uiso 1 1 calc R U . . .
C6 C 0.057(3) 0.6933(9) 1.0204(7) 0.048(3) Uani 1 1 d . . . . .
H6A H 0.1602 0.7408 1.0329 0.072 Uiso 1 1 calc R U . . .
H6B H -0.1326 0.7109 1.0238 0.072 Uiso 1 1 calc R U . . .
H6C H 0.1007 0.6374 1.0565 0.072 Uiso 1 1 calc R U . . .
C7 C -0.081(2) 0.5401(8) 0.8075(7) 0.039(3) Uani 1 1 d . . . . .
C8 C -0.200(2) 0.4968(8) 0.7736(7) 0.041(3) Uani 1 1 d . . . . .
C9 C -0.339(2) 0.4445(7) 0.7272(7) 0.037(3) Uani 1 1 d . . . . .
C10 C -0.314(2) 0.4603(7) 0.6489(7) 0.041(3) Uani 1 1 d . . . . .
C11 C -0.436(2) 0.4094(8) 0.6027(7) 0.042(3) Uani 1 1 d . . . . .
H11A H -0.4196 0.4215 0.5486 0.050 Uiso 1 1 calc R U . . .
C12 C -0.584(2) 0.3396(8) 0.6405(7) 0.043(3) Uani 1 1 d . . . . .
H12A H -0.6627 0.3019 0.6116 0.052 Uiso 1 1 calc R U . . .
C13 C -0.615(2) 0.3251(8) 0.7187(7) 0.037(3) Uani 1 1 d . . . . .
C14 C -0.494(2) 0.3779(8) 0.7631(8) 0.047(3) Uani 1 1 d . . . . .
H14A H -0.5172 0.3681 0.8170 0.057 Uiso 1 1 calc R U . . .
C15 C -0.534(3) 0.1566(9) 0.8103(9) 0.055(3) Uani 1 1 d . . . . .
H15A H -0.4469 0.1824 0.8492 0.082 Uiso 1 1 calc R U . . .
H15B H -0.6122 0.1015 0.8346 0.082 Uiso 1 1 calc R U . . .
H15C H -0.4024 0.1428 0.7722 0.082 Uiso 1 1 calc R U . . .
C16 C 0.584(2) 0.7602(7) 0.7880(7) 0.036(3) Uani 1 1 d . . . . .
C17 C 0.750(2) 0.8006(7) 0.7493(6) 0.034(2) Uani 1 1 d . . . . .
C18 C 0.945(2) 0.8460(7) 0.7022(7) 0.033(2) Uani 1 1 d . . . . .
C19 C 1.069(2) 0.9169(8) 0.7220(6) 0.035(2) Uani 1 1 d . . . . .
C20 C 1.259(2) 0.9593(8) 0.6748(7) 0.043(3) Uani 1 1 d . . . . .
H20A H 1.3428 1.0078 0.6888 0.052 Uiso 1 1 calc R U . . .
C21 C 1.327(3) 0.9305(9) 0.6074(7) 0.049(3) Uani 1 1 d . . . . .
H21A H 1.4527 0.9606 0.5738 0.059 Uiso 1 1 calc R U . . .
C22 C 1.212(2) 0.8582(8) 0.5888(7) 0.040(3) Uani 1 1 d . . . . .
C23 C 1.017(2) 0.8161(7) 0.6357(7) 0.037(3) Uani 1 1 d . . . . .
H23A H 0.9345 0.7673 0.6218 0.044 Uiso 1 1 calc R U . . .
C24 C 1.147(3) 0.8753(10) 0.4308(8) 0.062(4) Uani 1 1 d . . . . .
H24A H 1.1942 0.9377 0.4233 0.093 Uiso 1 1 calc R U . . .
H24B H 1.1921 0.8505 0.3847 0.093 Uiso 1 1 calc R U . . .
H24C H 0.9569 0.8731 0.4410 0.093 Uiso 1 1 calc R U . . .
O1S O 0.520(2) 0.8646(7) 0.9996(6) 0.061(3) Uani 1 1 d . . . . .


_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 C10 2.116(10) . ?
I2 C19 2.106(12) . ?
S1 O2 1.414(10) . ?
S1 O1 1.417(10) . ?
S1 C13 1.750(11) . ?
S1 C15 1.760(14) . ?
S2 O4 1.419(11) . ?
S2 O3 1.424(10) . ?
S2 C24 1.739(15) . ?
S2 C22 1.771(13) . ?
N1 C5 1.336(14) . ?
N1 C1 1.343(14) . ?
N1 C6 1.469(15) . ?
C1 C2 1.362(16) . ?
C1 H1B 0.9500 . ?
C2 C3 1.422(15) . ?
C2 C16 1.445(14) . ?
C3 C4 1.389(15) . ?
C3 H3B 0.9500 . ?
C4 C5 1.377(16) . ?
C4 C7 1.424(16) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.170(17) . ?
C8 C9 1.467(17) . ?
C9 C10 1.374(17) . ?
C9 C14 1.384(16) . ?
C10 C11 1.405(17) . ?
C11 C12 1.406(17) . ?
C11 H11A 0.9500 . ?
C12 C13 1.377(17) . ?
C12 H12A 0.9500 . ?
C13 C14 1.402(17) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.208(15) . ?
C17 C18 1.421(14) . ?
C18 C23 1.377(16) . ?
C18 C19 1.387(16) . ?
C19 C20 1.385(15) . ?
C20 C21 1.380(18) . ?
C20 H20A 0.9500 . ?
C21 C22 1.373(17) . ?
C21 H21A 0.9500 . ?
C22 C23 1.400(15) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
O2 S1 O1 118.5(6) . . ?
O2 S1 C13 108.3(6) . . ?
O1 S1 C13 107.9(6) . . ?
O2 S1 C15 109.0(7) . . ?
O1 S1 C15 107.6(7) . . ?
C13 S1 C15 104.7(6) . . ?
O4 S2 O3 118.5(7) . . ?
O4 S2 C24 108.7(7) . . ?
O3 S2 C24 108.5(7) . . ?
O4 S2 C22 108.5(6) . . ?
O3 S2 C22 106.3(6) . . ?
C24 S2 C22 105.6(7) . . ?
C5 N1 C1 120.9(10) . . ?
C5 N1 C6 119.4(10) . . ?
C1 N1 C6 119.6(10) . . ?
N1 C1 C2 120.4(10) . . ?
N1 C1 H1B 119.8 . . ?
C2 C1 H1B 119.8 . . ?
C1 C2 C3 119.9(9) . . ?
C1 C2 C16 121.0(10) . . ?
C3 C2 C16 119.1(10) . . ?
C4 C3 C2 118.1(10) . . ?
C4 C3 H3B 121.0 . . ?
C2 C3 H3B 121.0 . . ?
C5 C4 C3 118.6(10) . . ?
C5 C4 C7 122.7(10) . . ?
C3 C4 C7 118.6(11) . . ?
N1 C5 C4 122.0(10) . . ?
N1 C5 H5A 119.0 . . ?
C4 C5 H5A 119.0 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C4 174.0(13) . . ?
C7 C8 C9 176.7(13) . . ?
C10 C9 C14 120.0(11) . . ?
C10 C9 C8 120.7(10) . . ?
C14 C9 C8 119.3(11) . . ?
C9 C10 C11 122.4(10) . . ?
C9 C10 I1 120.4(9) . . ?
C11 C10 I1 117.2(8) . . ?
C12 C11 C10 116.7(11) . . ?
C12 C11 H11A 121.6 . . ?
C10 C11 H11A 121.6 . . ?
C13 C12 C11 121.1(11) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C12 C13 C14 120.8(11) . . ?
C12 C13 S1 120.4(9) . . ?
C14 C13 S1 118.6(9) . . ?
C9 C14 C13 118.9(12) . . ?
C9 C14 H14A 120.5 . . ?
C13 C14 H14A 120.5 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C2 177.7(12) . . ?
C16 C17 C18 178.2(12) . . ?
C23 C18 C19 119.5(9) . . ?
C23 C18 C17 118.0(10) . . ?
C19 C18 C17 122.5(10) . . ?
C20 C19 C18 120.9(11) . . ?
C20 C19 I2 118.8(9) . . ?
C18 C19 I2 120.1(8) . . ?
C21 C20 C19 119.5(11) . . ?
C21 C20 H20A 120.2 . . ?
C19 C20 H20A 120.2 . . ?
C22 C21 C20 119.9(11) . . ?
C22 C21 H21A 120.0 . . ?
C20 C21 H21A 120.0 . . ?
C21 C22 C23 120.7(12) . . ?
C21 C22 S2 120.5(9) . . ?
C23 C22 S2 118.8(9) . . ?
C18 C23 C22 119.4(10) . . ?
C18 C23 H23A 120.3 . . ?
C22 C23 H23A 120.3 . . ?
S2 C24 H24A 109.5 . . ?
S2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
C5 N1 C1 C2 0.6(16) . . . . ?
C6 N1 C1 C2 176.4(11) . . . . ?
N1 C1 C2 C3 -0.2(16) . . . . ?
N1 C1 C2 C16 178.8(10) . . . . ?
C1 C2 C3 C4 1.5(15) . . . . ?
C16 C2 C3 C4 -177.5(10) . . . . ?
C2 C3 C4 C5 -3.1(16) . . . . ?
C2 C3 C4 C7 174.7(10) . . . . ?
C1 N1 C5 C4 -2.4(16) . . . . ?
C6 N1 C5 C4 -178.1(11) . . . . ?
C3 C4 C5 N1 3.6(17) . . . . ?
C7 C4 C5 N1 -174.1(11) . . . . ?
C14 C9 C10 C11 -1.6(18) . . . . ?
C8 C9 C10 C11 177.5(11) . . . . ?
C14 C9 C10 I1 176.7(9) . . . . ?
C8 C9 C10 I1 -4.2(15) . . . . ?
C9 C10 C11 C12 -1.0(18) . . . . ?
I1 C10 C11 C12 -179.3(9) . . . . ?
C10 C11 C12 C13 2.8(18) . . . . ?
C11 C12 C13 C14 -2.0(19) . . . . ?
C11 C12 C13 S1 -176.5(10) . . . . ?
O2 S1 C13 C12 -10.4(12) . . . . ?
O1 S1 C13 C12 -139.9(10) . . . . ?
C15 S1 C13 C12 105.8(11) . . . . ?
O2 S1 C13 C14 175.0(10) . . . . ?
O1 S1 C13 C14 45.6(11) . . . . ?
C15 S1 C13 C14 -68.8(11) . . . . ?
C10 C9 C14 C13 2.3(17) . . . . ?
C8 C9 C14 C13 -176.7(11) . . . . ?
C12 C13 C14 C9 -0.6(18) . . . . ?
S1 C13 C14 C9 174.0(9) . . . . ?
C23 C18 C19 C20 1.4(17) . . . . ?
C17 C18 C19 C20 179.7(11) . . . . ?
C23 C18 C19 I2 -172.9(8) . . . . ?
C17 C18 C19 I2 5.4(15) . . . . ?
C18 C19 C20 C21 0.0(18) . . . . ?
I2 C19 C20 C21 174.4(10) . . . . ?
C19 C20 C21 C22 -2(2) . . . . ?
C20 C21 C22 C23 3(2) . . . . ?
C20 C21 C22 S2 -172.9(10) . . . . ?
O4 S2 C22 C21 157.5(11) . . . . ?
O3 S2 C22 C21 29.1(13) . . . . ?
C24 S2 C22 C21 -86.1(12) . . . . ?
O4 S2 C22 C23 -18.7(12) . . . . ?
O3 S2 C22 C23 -147.1(10) . . . . ?
C24 S2 C22 C23 97.7(11) . . . . ?
C19 C18 C23 C22 -0.4(17) . . . . ?
C17 C18 C23 C22 -178.8(11) . . . . ?
C21 C22 C23 C18 -1.9(18) . . . . ?
S2 C22 C23 C18 174.3(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B O1S 0.95 2.28 3.206(15) 165.5 .
C5 H5A Cl1 0.95 2.46 3.404(11) 169.8 1_456
C15 H15B I2 0.98 3.12 4.002(13) 149.9 1_345
C23 H23A I1 0.95 3.20 4.085(11) 155.6 1_655
C24 H24B O2 0.98 2.46 3.186(17) 131.0 2_566
C24 H24C O3 0.98 2.17 3.096(17) 158.2 1_455

_refine_diff_density_max         0.917
_refine_diff_density_min         -1.294
_refine_diff_density_rms         0.176



####################################################################### 
# 
# 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_cu_mh237_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1868185'
_audit_update_record             
;
2018-09-16 deposited with the CCDC.
2019-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 I3 N O4 S2'
_chemical_formula_weight         829.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.5565(5)
_cell_length_b                   13.3964(8)
_cell_length_c                   13.6335(8)
_cell_angle_alpha                64.031(4)
_cell_angle_beta                 79.229(4)
_cell_angle_gamma                86.953(4)
_cell_volume                     1379.49(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4559
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      66.65

_exptl_crystal_description       cut-block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    28.358
_shelx_estimated_absorpt_T_min   0.210
_shelx_estimated_absorpt_T_max   0.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4856
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13406
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.667
_diffrn_reflns_theta_max         66.871
_diffrn_reflns_theta_full        66.871
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             4799
_reflns_number_gt                3861
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0365P)²+0.9258P] 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         4799
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
I1 I 0.86426(5) 0.22071(4) 0.70492(3) 0.03327(13) Uani 1 1 d . . . . .
I2 I 0.56421(5) 0.44395(3) 0.26177(4) 0.03403(14) Uani 1 1 d . . . . .
I3 I 0.71412(6) 0.19912(4) 0.48411(4) 0.03764(14) Uani 1 1 d . . . . .
S1 S 1.11741(19) 0.31255(14) 1.09037(14) 0.0282(3) Uani 1 1 d . . . . .
S2 S 0.3783(2) 0.92657(14) -0.12060(14) 0.0308(4) Uani 1 1 d . . . . .
N1 N 0.7822(8) 0.8179(5) 0.4759(6) 0.0395(15) Uani 1 1 d . . . . .
O1 O 1.2104(7) 0.2229(5) 1.1529(5) 0.0493(15) Uani 1 1 d . . . . .
O2 O 1.1826(6) 0.4246(4) 1.0417(4) 0.0374(12) Uani 1 1 d . . . . .
O3 O 0.3179(7) 0.9970(4) -0.0671(5) 0.0442(13) Uani 1 1 d . . . . .
O4 O 0.2809(7) 0.9106(5) -0.1883(5) 0.0470(14) Uani 1 1 d . . . . .
C1 C 0.7591(7) 0.6133(6) 0.4804(5) 0.0267(14) Uani 1 1 d . . . . .
H1B H 0.7502 0.5421 0.4821 0.032 Uiso 1 1 calc R U . . .
C2 C 0.8282(8) 0.6257(6) 0.5592(5) 0.0268(14) Uani 1 1 d . . . . .
C3 C 0.8362(9) 0.7303(6) 0.5554(6) 0.0336(16) Uani 1 1 d . . . . .
H3B H 0.8805 0.7398 0.6097 0.040 Uiso 1 1 calc R U . . .
C4 C 0.7154(9) 0.8093(6) 0.3994(6) 0.0383(18) Uani 1 1 d . . . . .
H4B H 0.6759 0.8733 0.3452 0.046 Uiso 1 1 calc R U . . .
C5 C 0.7031(8) 0.7065(6) 0.3987(6) 0.0309(15) Uani 1 1 d . . . . .
C6 C 0.7905(17) 0.9281(8) 0.4765(11) 0.083(4) Uani 1 1 d . . . . .
H6A H 0.8426 0.9213 0.5372 0.124 Uiso 1 1 calc R U . . .
H6B H 0.8517 0.9810 0.4057 0.124 Uiso 1 1 calc R U . . .
H6C H 0.6826 0.9547 0.4870 0.124 Uiso 1 1 calc R U . . .
C7 C 0.8821(9) 0.5315(6) 0.6465(6) 0.0314(15) Uani 1 1 d . . . . .
C8 C 0.9207(8) 0.4523(6) 0.7218(5) 0.0274(14) Uani 1 1 d . . . . .
C9 C 0.9662(7) 0.3580(6) 0.8117(5) 0.0252(14) Uani 1 1 d . . . . .
C10 C 1.0206(8) 0.3756(5) 0.8942(5) 0.0249(14) Uani 1 1 d . . . . .
H10A H 1.0264 0.4486 0.8885 0.030 Uiso 1 1 calc R U . . .
C11 C 1.0654(8) 0.2873(6) 0.9830(5) 0.0250(13) Uani 1 1 d . . . . .
C12 C 1.0657(8) 0.1805(6) 0.9914(6) 0.0299(15) Uani 1 1 d . . . . .
H12A H 1.1019 0.1206 1.0515 0.036 Uiso 1 1 calc R U . . .
C13 C 1.0113(9) 0.1628(6) 0.9092(6) 0.0310(16) Uani 1 1 d . . . . .
H13A H 1.0107 0.0900 0.9138 0.037 Uiso 1 1 calc R U . . .
C14 C 0.9589(8) 0.2490(6) 0.8225(5) 0.0259(14) Uani 1 1 d . . . . .
C15 C 0.9329(9) 0.3090(7) 1.1742(6) 0.0346(17) Uani 1 1 d . . . . .
H15A H 0.8688 0.3701 1.1318 0.052 Uiso 1 1 calc R U . . .
H15B H 0.8767 0.2380 1.1979 0.052 Uiso 1 1 calc R U . . .
H15C H 0.9501 0.3169 1.2395 0.052 Uiso 1 1 calc R U . . .
C16 C 0.6365(8) 0.6989(6) 0.3133(6) 0.0308(16) Uani 1 1 d . . . . .
C17 C 0.5845(8) 0.6944(6) 0.2407(6) 0.0294(15) Uani 1 1 d . . . . .
C18 C 0.5203(7) 0.6936(6) 0.1507(5) 0.0248(14) Uani 1 1 d . . . . .
C19 C 0.4821(8) 0.7942(6) 0.0696(6) 0.0272(14) Uani 1 1 d . . . . .
H19A H 0.5000 0.8618 0.0732 0.033 Uiso 1 1 calc R U . . .
C20 C 0.4174(8) 0.7949(5) -0.0170(5) 0.0247(14) Uani 1 1 d . . . . .
C22 C 0.4255(8) 0.5970(5) 0.0595(6) 0.0294(16) Uani 1 1 d . . . . .
H22A H 0.4032 0.5292 0.0577 0.035 Uiso 1 1 calc R U . . .
C23 C 0.4948(7) 0.5954(5) 0.1438(5) 0.0215(13) Uani 1 1 d . . . . .
C24 C 0.5665(10) 0.9783(7) -0.1979(8) 0.060(3) Uani 1 1 d . . . . .
H24A H 0.6318 0.9889 -0.1511 0.090 Uiso 1 1 calc R U . . .
H24B H 0.6170 0.9255 -0.2250 0.090 Uiso 1 1 calc R U . . .
H24C H 0.5567 1.0496 -0.2611 0.090 Uiso 1 1 calc R U . . .
C21 C 0.3882(8) 0.6977(5) -0.0230(5) 0.0269(14) Uani 1 1 d . . . . .
H21A H 0.3434 0.6993 -0.0824 0.032 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 C14 2.102(7) . ?
I2 C23 2.104(6) . ?
S1 O1 1.434(6) . ?
S1 O2 1.443(5) . ?
S1 C15 1.757(7) . ?
S1 C11 1.774(7) . ?
S2 O4 1.439(6) . ?
S2 O3 1.449(6) . ?
S2 C24 1.741(8) . ?
S2 C20 1.775(7) . ?
N1 C4 1.328(10) . ?
N1 C3 1.334(10) . ?
N1 C6 1.487(10) . ?
C1 C2 1.391(10) . ?
C1 C5 1.396(10) . ?
C1 H1B 0.9500 . ?
C2 C3 1.385(10) . ?
C2 C7 1.432(10) . ?
C3 H3B 0.9500 . ?
C4 C5 1.391(10) . ?
C4 H4B 0.9500 . ?
C5 C16 1.431(10) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.193(10) . ?
C8 C9 1.422(10) . ?
C9 C10 1.406(9) . ?
C9 C14 1.405(9) . ?
C10 C11 1.371(10) . ?
C10 H10A 0.9500 . ?
C11 C12 1.384(10) . ?
C12 C13 1.403(10) . ?
C12 H12A 0.9500 . ?
C13 C14 1.371(10) . ?
C13 H13A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.184(11) . ?
C17 C18 1.439(10) . ?
C18 C23 1.391(9) . ?
C18 C19 1.389(10) . ?
C19 C20 1.390(10) . ?
C19 H19A 0.9500 . ?
C20 C21 1.379(9) . ?
C22 C23 1.380(10) . ?
C22 C21 1.396(10) . ?
C22 H22A 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C21 H21A 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
O1 S1 O2 118.8(4) . . ?
O1 S1 C15 109.1(4) . . ?
O2 S1 C15 107.4(3) . . ?
O1 S1 C11 109.0(3) . . ?
O2 S1 C11 108.0(3) . . ?
C15 S1 C11 103.5(3) . . ?
O4 S2 O3 117.3(4) . . ?
O4 S2 C24 110.1(5) . . ?
O3 S2 C24 108.0(4) . . ?
O4 S2 C20 108.9(3) . . ?
O3 S2 C20 108.4(3) . . ?
C24 S2 C20 103.3(4) . . ?
C4 N1 C3 122.5(7) . . ?
C4 N1 C6 118.9(7) . . ?
C3 N1 C6 118.5(7) . . ?
C2 C1 C5 119.3(6) . . ?
C2 C1 H1B 120.3 . . ?
C5 C1 H1B 120.3 . . ?
C3 C2 C1 118.7(7) . . ?
C3 C2 C7 120.3(6) . . ?
C1 C2 C7 120.9(6) . . ?
N1 C3 C2 120.5(7) . . ?
N1 C3 H3B 119.8 . . ?
C2 C3 H3B 119.8 . . ?
N1 C4 C5 119.9(7) . . ?
N1 C4 H4B 120.0 . . ?
C5 C4 H4B 120.0 . . ?
C4 C5 C1 119.0(7) . . ?
C4 C5 C16 119.5(7) . . ?
C1 C5 C16 121.5(7) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C2 177.2(8) . . ?
C7 C8 C9 179.8(8) . . ?
C10 C9 C14 118.7(6) . . ?
C10 C9 C8 117.7(6) . . ?
C14 C9 C8 123.6(6) . . ?
C11 C10 C9 120.0(6) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C10 C11 C12 121.6(6) . . ?
C10 C11 S1 118.2(5) . . ?
C12 C11 S1 120.2(5) . . ?
C11 C12 C13 118.4(7) . . ?
C11 C12 H12A 120.8 . . ?
C13 C12 H12A 120.8 . . ?
C14 C13 C12 121.0(6) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C9 120.2(6) . . ?
C13 C14 I1 120.9(5) . . ?
C9 C14 I1 118.9(5) . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C5 178.3(8) . . ?
C16 C17 C18 177.7(8) . . ?
C23 C18 C19 119.7(6) . . ?
C23 C18 C17 121.8(6) . . ?
C19 C18 C17 118.5(6) . . ?
C18 C19 C20 119.3(6) . . ?
C18 C19 H19A 120.3 . . ?
C20 C19 H19A 120.3 . . ?
C21 C20 C19 121.3(6) . . ?
C21 C20 S2 121.6(5) . . ?
C19 C20 S2 117.0(5) . . ?
C23 C22 C21 120.3(6) . . ?
C23 C22 H22A 119.8 . . ?
C21 C22 H22A 119.8 . . ?
C22 C23 C18 120.3(6) . . ?
C22 C23 I2 119.9(5) . . ?
C18 C23 I2 119.8(5) . . ?
S2 C24 H24A 109.5 . . ?
S2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C21 C22 118.9(6) . . ?
C20 C21 H21A 120.5 . . ?
C22 C21 H21A 120.5 . . ?

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
C5 C1 C2 C3 1.3(9) . . . . ?
C5 C1 C2 C7 177.9(6) . . . . ?
C4 N1 C3 C2 1.8(12) . . . . ?
C6 N1 C3 C2 178.8(9) . . . . ?
C1 C2 C3 N1 -1.6(11) . . . . ?
C7 C2 C3 N1 -178.2(7) . . . . ?
C3 N1 C4 C5 -1.6(12) . . . . ?
C6 N1 C4 C5 -178.6(9) . . . . ?
N1 C4 C5 C1 1.2(11) . . . . ?
N1 C4 C5 C16 -177.6(7) . . . . ?
C2 C1 C5 C4 -1.1(10) . . . . ?
C2 C1 C5 C16 177.7(6) . . . . ?
C14 C9 C10 C11 0.0(9) . . . . ?
C8 C9 C10 C11 179.8(6) . . . . ?
C9 C10 C11 C12 3.1(10) . . . . ?
C9 C10 C11 S1 -174.8(5) . . . . ?
O1 S1 C11 C10 -160.2(5) . . . . ?
O2 S1 C11 C10 -29.9(6) . . . . ?
C15 S1 C11 C10 83.7(6) . . . . ?
O1 S1 C11 C12 21.8(7) . . . . ?
O2 S1 C11 C12 152.2(5) . . . . ?
C15 S1 C11 C12 -94.2(6) . . . . ?
C10 C11 C12 C13 -3.1(10) . . . . ?
S1 C11 C12 C13 174.8(5) . . . . ?
C11 C12 C13 C14 0.0(10) . . . . ?
C12 C13 C14 C9 3.0(10) . . . . ?
C12 C13 C14 I1 -176.2(5) . . . . ?
C10 C9 C14 C13 -3.0(9) . . . . ?
C8 C9 C14 C13 177.2(6) . . . . ?
C10 C9 C14 I1 176.2(4) . . . . ?
C8 C9 C14 I1 -3.6(8) . . . . ?
C23 C18 C19 C20 0.6(9) . . . . ?
C17 C18 C19 C20 -178.9(6) . . . . ?
C18 C19 C20 C21 1.0(10) . . . . ?
C18 C19 C20 S2 -177.7(5) . . . . ?
O4 S2 C20 C21 14.0(7) . . . . ?
O3 S2 C20 C21 142.6(6) . . . . ?
C24 S2 C20 C21 -103.1(7) . . . . ?
O4 S2 C20 C19 -167.4(5) . . . . ?
O3 S2 C20 C19 -38.7(6) . . . . ?
C24 S2 C20 C19 75.6(7) . . . . ?
C21 C22 C23 C18 3.4(9) . . . . ?
C21 C22 C23 I2 -176.0(5) . . . . ?
C19 C18 C23 C22 -2.8(9) . . . . ?
C17 C18 C23 C22 176.7(6) . . . . ?
C19 C18 C23 I2 176.7(4) . . . . ?
C17 C18 C23 I2 -3.9(8) . . . . ?
C19 C20 C21 C22 -0.4(10) . . . . ?
S2 C20 C21 C22 178.3(5) . . . . ?
C23 C22 C21 C20 -1.9(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15A I2 0.98 3.23 3.811(7) 119.4 1_556
C15 H15B O4 0.98 2.53 3.461(9) 159.6 2_666
C15 H15C I3 0.98 3.30 3.926(6) 123.3 1_556
C19 H19A O3 0.95 2.48 3.340(8) 150.9 2_675
C22 H22A O2 0.95 2.51 3.303(8) 141.5 1_454
C24 H24B O1 0.98 2.37 3.119(10) 132.7 2_766
C24 H24C I3 0.98 3.21 4.032(8) 142.0 1_564

_refine_diff_density_max         0.924
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.154



####################################################################### 
# 
# 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_cu_dwj245_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1875924'
_audit_update_record             
;
2018-10-27 deposited with the CCDC.
2019-01-16 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            'C24 H20 Br I2 N O5 S2'
_chemical_formula_weight         800.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   5.1366(3)
_cell_length_b                   15.3534(7)
_cell_length_c                   17.7446(9)
_cell_angle_alpha                78.460(3)
_cell_angle_beta                 89.369(4)
_cell_angle_gamma                86.064(4)
_cell_volume                     1367.89(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3704
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      66.56

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    21.494
_shelx_estimated_absorpt_T_min   0.153
_shelx_estimated_absorpt_T_max   0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3375
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15563
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.541
_diffrn_reflns_theta_max         66.650
_diffrn_reflns_theta_full        66.650
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4812
_reflns_number_gt                3717
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0358P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4812
_refine_ls_number_parameters     327
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
I1 I -0.08968(8) 0.56639(3) 0.59057(2) 0.04027(13) Uani 1 1 d . . . . .
I2 I 0.99183(8) 0.95564(2) 0.81945(2) 0.03516(12) Uani 1 1 d . . . . .
Br1 Br 0.500000 0.500000 0.000000 0.0609(4) Uani 1 2 d S . P . .
Br2 Br 1.000000 0.000000 0.000000 0.0634(4) Uani 1 2 d S . P . .
S1 S -0.7855(3) 0.23955(10) 0.77013(9) 0.0333(3) Uani 1 1 d . . . . .
S2 S 1.3330(3) 0.81105(11) 0.50313(9) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.1269(8) 0.6842(3) 0.9353(3) 0.0235(10) Uani 1 1 d . . . . .
O1 O -0.9395(8) 0.2701(3) 0.8289(3) 0.0462(11) Uani 1 1 d . . . . .
O2 O -0.9158(9) 0.2023(3) 0.7135(3) 0.0557(14) Uani 1 1 d . . . . .
O3 O 1.2675(10) 0.7202(3) 0.5166(3) 0.0573(14) Uani 1 1 d . . . . .
O4 O 1.6011(8) 0.8313(4) 0.4919(3) 0.0570(15) Uani 1 1 d . . . . .
C1 C 0.0039(10) 0.6220(3) 0.9082(3) 0.0255(12) Uani 1 1 d . . . . .
H1B H -0.125537 0.590064 0.938476 0.031 Uiso 1 1 calc R U . . .
C2 C 0.0662(10) 0.6047(3) 0.8364(3) 0.0261(12) Uani 1 1 d . . . . .
C3 C 0.2616(10) 0.6488(3) 0.7937(3) 0.0239(12) Uani 1 1 d . . . . .
H3B H 0.307907 0.636307 0.744785 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3917(10) 0.7127(3) 0.8238(3) 0.0229(11) Uani 1 1 d . . . . .
C5 C 0.3165(11) 0.7289(3) 0.8948(3) 0.0262(12) Uani 1 1 d . . . . .
H5A H 0.399693 0.772360 0.915453 0.031 Uiso 1 1 calc R U . . .
C6 C 0.0606(12) 0.6992(4) 1.0133(4) 0.0385(15) Uani 1 1 d . . . . .
H6A H 0.164320 0.745926 1.025198 0.058 Uiso 1 1 calc R U . . .
H6B H -0.125445 0.717575 1.015290 0.058 Uiso 1 1 calc R U . . .
H6C H 0.098909 0.643836 1.050985 0.058 Uiso 1 1 calc R U . . .
C7 C -0.0801(11) 0.5432(4) 0.8051(3) 0.0282(12) Uani 1 1 d . . . . .
C8 C -0.1959(11) 0.4995(4) 0.7719(3) 0.0293(13) Uani 1 1 d . . . . .
C9 C -0.3349(10) 0.4479(4) 0.7279(3) 0.0261(12) Uani 1 1 d . . . . .
C10 C -0.3090(11) 0.4631(3) 0.6476(3) 0.0277(12) Uani 1 1 d . . . . .
C11 C -0.4316(12) 0.4109(4) 0.6049(4) 0.0340(14) Uani 1 1 d . . . . .
H11A H -0.414719 0.421817 0.550541 0.041 Uiso 1 1 calc R U . . .
C12 C -0.5796(11) 0.3425(4) 0.6426(4) 0.0345(14) Uani 1 1 d . . . . .
H12A H -0.660393 0.305347 0.614325 0.041 Uiso 1 1 calc R U . . .
C13 C -0.6075(11) 0.3295(4) 0.7209(3) 0.0303(13) Uani 1 1 d . . . . .
C14 C -0.4865(11) 0.3807(4) 0.7644(3) 0.0293(13) Uani 1 1 d . . . . .
H14A H -0.507179 0.369858 0.818652 0.035 Uiso 1 1 calc R U . . .
C15 C -0.5410(12) 0.1613(4) 0.8139(4) 0.0436(16) Uani 1 1 d . . . . .
H15A H -0.434668 0.140046 0.774197 0.065 Uiso 1 1 calc R U . . .
H15B H -0.430192 0.189209 0.845596 0.065 Uiso 1 1 calc R U . . .
H15C H -0.621241 0.110970 0.846376 0.065 Uiso 1 1 calc R U . . .
C16 C 0.5859(10) 0.7609(3) 0.7802(3) 0.0235(12) Uani 1 1 d . . . . .
C17 C 0.7509(10) 0.8013(3) 0.7419(3) 0.0230(11) Uani 1 1 d . . . . .
C18 C 0.9474(10) 0.8460(4) 0.6954(3) 0.0251(12) Uani 1 1 d . . . . .
C19 C 1.0723(10) 0.9172(3) 0.7148(3) 0.0245(12) Uani 1 1 d . . . . .
C20 C 1.2628(11) 0.9581(4) 0.6667(3) 0.0319(13) Uani 1 1 d . . . . .
H20A H 1.342643 1.007305 0.679421 0.038 Uiso 1 1 calc R U . . .
C21 C 1.3376(11) 0.9285(4) 0.6011(3) 0.0322(13) Uani 1 1 d . . . . .
H21A H 1.468777 0.956623 0.568712 0.039 Uiso 1 1 calc R U . . .
C22 C 1.2185(10) 0.8568(4) 0.5826(3) 0.0265(12) Uani 1 1 d . . . . .
C23 C 1.0237(10) 0.8158(4) 0.6286(3) 0.0269(12) Uani 1 1 d . . . . .
H23A H 0.942352 0.767553 0.614701 0.032 Uiso 1 1 calc R U . . .
C24 C 1.1568(12) 0.8692(5) 0.4239(4) 0.0455(17) Uani 1 1 d . . . . .
H24A H 1.199019 0.931805 0.413727 0.068 Uiso 1 1 calc R U . . .
H24B H 1.202244 0.843248 0.378983 0.068 Uiso 1 1 calc R U . . .
H24C H 0.969724 0.865574 0.434327 0.068 Uiso 1 1 calc R U . . .
O1S O 0.5218(10) 0.8595(4) 0.9921(3) 0.0553(14) Uani 1 1 d D . . . .
H1S H 0.672(11) 0.897(5) 0.991(5) 0.10(3) Uiso 1 1 d D . . . .
H2S H 0.368(10) 0.900(5) 0.999(5) 0.10(3) Uiso 1 1 d D . . . .


_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 C10 2.095(5) . ?
I2 C19 2.087(5) . ?
S1 O1 1.435(5) . ?
S1 O2 1.443(4) . ?
S1 C15 1.750(6) . ?
S1 C13 1.783(6) . ?
S2 O3 1.430(5) . ?
S2 O4 1.436(5) . ?
S2 C24 1.734(6) . ?
S2 C22 1.775(5) . ?
N1 C1 1.347(7) . ?
N1 C5 1.348(7) . ?
N1 C6 1.479(7) . ?
C1 C2 1.382(8) . ?
C1 H1B 0.9500 . ?
C2 C3 1.383(8) . ?
C2 C7 1.444(7) . ?
C3 C4 1.415(7) . ?
C3 H3B 0.9500 . ?
C4 C5 1.378(7) . ?
C4 C16 1.413(8) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.170(8) . ?
C8 C9 1.444(8) . ?
C9 C14 1.386(8) . ?
C9 C10 1.404(8) . ?
C10 C11 1.391(8) . ?
C11 C12 1.395(9) . ?
C11 H11A 0.9500 . ?
C12 C13 1.371(8) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(8) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.207(8) . ?
C17 C18 1.421(8) . ?
C18 C23 1.400(8) . ?
C18 C19 1.406(8) . ?
C19 C20 1.390(8) . ?
C20 C21 1.374(8) . ?
C20 H20A 0.9500 . ?
C21 C22 1.391(8) . ?
C21 H21A 0.9500 . ?
C22 C23 1.387(8) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O1S H1S 0.99(2) . ?
O1S H2S 1.00(2) . ?

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
O1 S1 O2 118.5(3) . . ?
O1 S1 C15 108.9(3) . . ?
O2 S1 C15 108.3(3) . . ?
O1 S1 C13 108.4(3) . . ?
O2 S1 C13 108.2(3) . . ?
C15 S1 C13 103.4(3) . . ?
O3 S2 O4 119.4(3) . . ?
O3 S2 C24 108.2(3) . . ?
O4 S2 C24 107.9(3) . . ?
O3 S2 C22 107.7(3) . . ?
O4 S2 C22 106.8(3) . . ?
C24 S2 C22 106.1(3) . . ?
C1 N1 C5 121.5(5) . . ?
C1 N1 C6 118.5(5) . . ?
C5 N1 C6 120.0(5) . . ?
N1 C1 C2 120.0(5) . . ?
N1 C1 H1B 120.0 . . ?
C2 C1 H1B 120.0 . . ?
C1 C2 C3 120.0(5) . . ?
C1 C2 C7 119.8(5) . . ?
C3 C2 C7 120.2(5) . . ?
C2 C3 C4 119.1(5) . . ?
C2 C3 H3B 120.4 . . ?
C4 C3 H3B 120.4 . . ?
C5 C4 C3 118.3(5) . . ?
C5 C4 C16 121.3(5) . . ?
C3 C4 C16 120.3(5) . . ?
N1 C5 C4 121.1(5) . . ?
N1 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C2 172.6(6) . . ?
C7 C8 C9 177.5(7) . . ?
C14 C9 C10 119.3(5) . . ?
C14 C9 C8 120.7(5) . . ?
C10 C9 C8 120.0(5) . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 I1 119.3(4) . . ?
C9 C10 I1 120.2(4) . . ?
C10 C11 C12 119.4(6) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C13 C12 C11 119.4(5) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 121.9(6) . . ?
C12 C13 S1 119.7(4) . . ?
C14 C13 S1 118.2(5) . . ?
C13 C14 C9 119.4(6) . . ?
C13 C14 H14A 120.3 . . ?
C9 C14 H14A 120.3 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C4 178.8(6) . . ?
C16 C17 C18 177.8(6) . . ?
C23 C18 C19 118.9(5) . . ?
C23 C18 C17 118.2(5) . . ?
C19 C18 C17 122.9(5) . . ?
C20 C19 C18 120.0(5) . . ?
C20 C19 I2 119.8(4) . . ?
C18 C19 I2 120.1(4) . . ?
C21 C20 C19 121.0(5) . . ?
C21 C20 H20A 119.5 . . ?
C19 C20 H20A 119.5 . . ?
C20 C21 C22 119.1(5) . . ?
C20 C21 H21A 120.5 . . ?
C22 C21 H21A 120.5 . . ?
C21 C22 C23 121.2(5) . . ?
C21 C22 S2 119.7(4) . . ?
C23 C22 S2 118.9(4) . . ?
C22 C23 C18 119.7(5) . . ?
C22 C23 H23A 120.1 . . ?
C18 C23 H23A 120.1 . . ?
S2 C24 H24A 109.5 . . ?
S2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H1S O1S H2S 104(7) . . ?

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
C5 N1 C1 C2 -1.9(8) . . . . ?
C6 N1 C1 C2 -178.3(5) . . . . ?
N1 C1 C2 C3 2.5(8) . . . . ?
N1 C1 C2 C7 -175.1(5) . . . . ?
C1 C2 C3 C4 -1.3(8) . . . . ?
C7 C2 C3 C4 176.3(5) . . . . ?
C2 C3 C4 C5 -0.4(8) . . . . ?
C2 C3 C4 C16 -177.8(5) . . . . ?
C1 N1 C5 C4 0.1(8) . . . . ?
C6 N1 C5 C4 176.4(5) . . . . ?
C3 C4 C5 N1 1.0(8) . . . . ?
C16 C4 C5 N1 178.4(5) . . . . ?
C14 C9 C10 C11 -0.6(8) . . . . ?
C8 C9 C10 C11 176.8(5) . . . . ?
C14 C9 C10 I1 178.3(4) . . . . ?
C8 C9 C10 I1 -4.3(7) . . . . ?
C9 C10 C11 C12 -0.6(9) . . . . ?
I1 C10 C11 C12 -179.5(4) . . . . ?
C10 C11 C12 C13 1.8(9) . . . . ?
C11 C12 C13 C14 -1.9(9) . . . . ?
C11 C12 C13 S1 -177.5(5) . . . . ?
O1 S1 C13 C12 -139.9(5) . . . . ?
O2 S1 C13 C12 -10.2(6) . . . . ?
C15 S1 C13 C12 104.6(5) . . . . ?
O1 S1 C13 C14 44.3(5) . . . . ?
O2 S1 C13 C14 174.0(5) . . . . ?
C15 S1 C13 C14 -71.2(5) . . . . ?
C12 C13 C14 C9 0.8(9) . . . . ?
S1 C13 C14 C9 176.5(4) . . . . ?
C10 C9 C14 C13 0.5(8) . . . . ?
C8 C9 C14 C13 -176.9(5) . . . . ?
C23 C18 C19 C20 1.9(8) . . . . ?
C17 C18 C19 C20 -179.9(5) . . . . ?
C23 C18 C19 I2 -173.7(4) . . . . ?
C17 C18 C19 I2 4.5(7) . . . . ?
C18 C19 C20 C21 -1.9(9) . . . . ?
I2 C19 C20 C21 173.7(4) . . . . ?
C19 C20 C21 C22 0.4(9) . . . . ?
C20 C21 C22 C23 1.0(9) . . . . ?
C20 C21 C22 S2 -174.2(4) . . . . ?
O3 S2 C22 C21 154.6(5) . . . . ?
O4 S2 C22 C21 25.1(6) . . . . ?
C24 S2 C22 C21 -89.8(5) . . . . ?
O3 S2 C22 C23 -20.8(5) . . . . ?
O4 S2 C22 C23 -150.2(5) . . . . ?
C24 S2 C22 C23 94.9(5) . . . . ?
C21 C22 C23 C18 -1.0(9) . . . . ?
S2 C22 C23 C18 174.2(4) . . . . ?
C19 C18 C23 C22 -0.4(8) . . . . ?
C17 C18 C23 C22 -178.8(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1B Br1 0.95 2.55 3.495(6) 171.1 1_456 yes
C5 H5A O1S 0.95 2.21 3.135(7) 163.6 . yes
C6 H6A O1S 0.98 2.60 3.497(8) 152.0 . yes
C15 H15C I2 0.98 3.32 4.081(6) 136.3 1_345 yes
C23 H23A I1 0.95 3.22 4.100(6) 155.4 1_655 yes
C24 H24B O2 0.98 2.45 3.164(7) 129.4 2_566 yes
C24 H24C O4 0.98 2.19 3.133(7) 161.6 1_455 yes
O1S H1S Br2 0.99(2) 2.42(2) 3.400(5) 172(7) 1_566 yes
O1S H2S Br2 1.00(2) 2.35(2) 3.343(5) 173(7) 1_466 yes

_refine_diff_density_max         0.732
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.122



