# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_mo_d8v21344_0m
_database_code_depnum_ccdc_archive 'CCDC 2083431'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2023-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 I3 N'
_chemical_formula_weight         540.93

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'

_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                   8.6649(8)
_cell_length_b                   8.8569(8)
_cell_length_c                   9.8661(9)
_cell_angle_alpha                84.893(3)
_cell_angle_beta                 88.222(3)
_cell_angle_gamma                84.477(3)
_cell_volume                     750.47(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7988
_cell_measurement_theta_min      4.638
_cell_measurement_theta_max      54.720

_exptl_crystal_description       prismatic
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.394
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    6.221
_shelx_estimated_absorpt_T_min   0.418
_shelx_estimated_absorpt_T_max   0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3136
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13556
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.073
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2914
_reflns_number_gt                2531
_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-2013 (Sheldrick, 2013)'
_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)+(0.1171P)²+14.9671P] 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         2914
_refine_ls_number_parameters     164
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.2527
_refine_ls_wR_factor_gt          0.2460
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001

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 0.69141(15) 0.77132(14) 0.03212(12) 0.0665(4) Uani 1 1 d . . . . .
I2 I 0.66947(16) 0.13134(13) 0.33134(14) 0.0715(4) Uani 1 1 d . . . . .
I3 I 0.11157(15) 0.27512(15) 0.56332(14) 0.0736(4) Uani 1 1 d . . . . .
N1 N 0.4682(15) 0.5692(15) 0.1864(13) 0.053(3) Uani 1 1 d . . . . .
C1 C 0.6181(16) 0.5777(18) 0.1473(15) 0.050(3) Uani 1 1 d . . . . .
C2 C 0.7122(15) 0.4474(16) 0.1835(15) 0.046(3) Uani 1 1 d . . . . .
C3 C 0.6100(18) 0.3558(17) 0.2527(17) 0.052(3) Uani 1 1 d . . . . .
C4 C 0.4591(16) 0.4296(17) 0.2570(15) 0.047(3) Uani 1 1 d . . . . .
C5 C 0.3184(18) 0.369(2) 0.3175(16) 0.056(4) Uani 1 1 d . . . . .
H5A H 0.3240 0.2605 0.3063 0.067 Uiso 1 1 calc R U . . .
H5B H 0.2290 0.4175 0.2685 0.067 Uiso 1 1 calc R U . . .
C6 C 0.295(2) 0.392(3) 0.4701(19) 0.074(5) Uani 1 1 d . . . . .
H6A H 0.2725 0.5003 0.4801 0.089 Uiso 1 1 calc R U . . .
H6B H 0.3899 0.3577 0.5170 0.089 Uiso 1 1 calc R U . . .
C7 C 0.880(2) 0.414(3) 0.160(2) 0.077(6) Uani 1 1 d . . . . .
H7A H 0.9182 0.4940 0.0999 0.116 Uiso 1 1 calc R U . . .
H7B H 0.8987 0.3192 0.1184 0.116 Uiso 1 1 calc R U . . .
H7C H 0.9321 0.4058 0.2446 0.116 Uiso 1 1 calc R U . . .
C8 C 0.339(2) 0.6868(19) 0.1636(18) 0.064(4) Uani 1 1 d D . . . .
H8A H 0.2444 0.6381 0.1538 0.077 Uiso 1 1 calc R U . A 1
H8B H 0.3575 0.7477 0.0791 0.077 Uiso 1 1 calc R U . A 1
C9 C 0.315(3) 0.790(2) 0.277(3) 0.054(4) Uani 0.5 1 d D U P B 1
H9A H 0.4148 0.8223 0.2961 0.064 Uiso 0.5 1 calc R U P B 1
H9B H 0.2817 0.7290 0.3575 0.064 Uiso 0.5 1 calc R U P B 1
C10 C 0.201(3) 0.931(3) 0.259(3) 0.052(3) Uani 0.5 1 d D U P B 1
H10 H 0.2029 1.0074 0.3180 0.063 Uiso 0.5 1 calc R U P B 1
C11 C 0.104(3) 0.945(4) 0.164(3) 0.047(4) Uani 0.5 1 d D U P B 1
H11A H 0.1031 0.8679 0.1057 0.057 Uiso 0.5 1 calc R U P B 1
H11B H 0.0346 1.0310 0.1530 0.057 Uiso 0.5 1 calc R U P B 1
C9' C 0.353(4) 0.806(3) 0.259(3) 0.053(4) Uani 0.5 1 d D U P B 2
H9'1 H 0.3054 0.7755 0.3467 0.064 Uiso 0.5 1 calc R U P B 2
H9'2 H 0.4613 0.8159 0.2735 0.064 Uiso 0.5 1 calc R U P B 2
C10' C 0.281(3) 0.948(3) 0.210(3) 0.054(3) Uani 0.5 1 d D U P B 2
H10' H 0.3363 1.0270 0.1732 0.065 Uiso 0.5 1 calc R U P B 2
C11' C 0.129(3) 0.959(3) 0.218(3) 0.043(4) Uani 0.5 1 d D U P B 2
H11C H 0.0780 0.8771 0.2552 0.051 Uiso 0.5 1 calc R U P B 2
H11D H 0.0727 1.0496 0.1871 0.051 Uiso 0.5 1 calc R U P B 2


_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 2.111(16) . ?
I2 C3 2.091(15) . ?
I3 C6 2.120(18) . ?
N1 C1 1.350(19) . ?
N1 C4 1.37(2) . ?
N1 C8 1.47(2) . ?
C1 C2 1.37(2) . ?
C2 C3 1.38(2) . ?
C2 C7 1.47(2) . ?
C3 C4 1.41(2) . ?
C4 C5 1.47(2) . ?
C5 C6 1.54(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9' 1.497(19) . ?
C8 C9 1.502(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.514(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.270(19) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?
C9' C10' 1.40(4) . ?
C9' H9'1 0.9700 . ?
C9' H9'2 0.9700 . ?
C10' C11' 1.307(19) . ?
C10' H10' 0.9300 . ?
C11' H11C 0.9300 . ?
C11' H11D 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
C1 N1 C4 107.1(13) . . ?
C1 N1 C8 127.5(14) . . ?
C4 N1 C8 125.4(13) . . ?
N1 C1 C2 113.6(14) . . ?
N1 C1 I1 121.6(11) . . ?
C2 C1 I1 124.8(11) . . ?
C1 C2 C3 102.3(12) . . ?
C1 C2 C7 129.5(16) . . ?
C3 C2 C7 128.2(15) . . ?
C2 C3 C4 111.4(13) . . ?
C2 C3 I2 124.3(11) . . ?
C4 C3 I2 124.2(12) . . ?
N1 C4 C3 105.5(13) . . ?
N1 C4 C5 126.6(14) . . ?
C3 C4 C5 127.8(15) . . ?
C4 C5 C6 113.4(13) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 I3 113.0(12) . . ?
C5 C6 H6A 109.0 . . ?
I3 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
I3 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9' 108.2(18) . . ?
N1 C8 C9 113.0(16) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 119(2) . . ?
C8 C9 H9A 107.5 . . ?
C10 C9 H9A 107.5 . . ?
C8 C9 H9B 107.5 . . ?
C10 C9 H9B 107.5 . . ?
H9A C9 H9B 107.0 . . ?
C11 C10 C9 120(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C10' C9' C8 112(3) . . ?
C10' C9' H9'1 109.3 . . ?
C8 C9' H9'1 109.3 . . ?
C10' C9' H9'2 109.3 . . ?
C8 C9' H9'2 109.3 . . ?
H9'1 C9' H9'2 107.9 . . ?
C11' C10' C9' 115(2) . . ?
C11' C10' H10' 122.7 . . ?
C9' C10' H10' 122.7 . . ?
C10' C11' H11C 120.0 . . ?
C10' C11' H11D 120.0 . . ?
H11C C11' H11D 120.0 . . ?

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
C4 N1 C1 C2 2.3(17) . . . . ?
C8 N1 C1 C2 -179.7(14) . . . . ?
C4 N1 C1 I1 179.1(10) . . . . ?
C8 N1 C1 I1 -3(2) . . . . ?
N1 C1 C2 C3 -1.6(17) . . . . ?
I1 C1 C2 C3 -178.2(10) . . . . ?
N1 C1 C2 C7 -179.9(16) . . . . ?
I1 C1 C2 C7 3(2) . . . . ?
C1 C2 C3 C4 0.2(16) . . . . ?
C7 C2 C3 C4 178.5(16) . . . . ?
C1 C2 C3 I2 177.0(11) . . . . ?
C7 C2 C3 I2 -5(2) . . . . ?
C1 N1 C4 C3 -2.0(16) . . . . ?
C8 N1 C4 C3 -180.0(14) . . . . ?
C1 N1 C4 C5 -179.1(14) . . . . ?
C8 N1 C4 C5 3(2) . . . . ?
C2 C3 C4 N1 1.1(17) . . . . ?
I2 C3 C4 N1 -175.6(10) . . . . ?
C2 C3 C4 C5 178.1(14) . . . . ?
I2 C3 C4 C5 1(2) . . . . ?
N1 C4 C5 C6 -96(2) . . . . ?
C3 C4 C5 C6 87(2) . . . . ?
C4 C5 C6 I3 -171.2(12) . . . . ?
C1 N1 C8 C9' -75(2) . . . . ?
C4 N1 C8 C9' 103(2) . . . . ?
C1 N1 C8 C9 -90(2) . . . . ?
C4 N1 C8 C9 87(2) . . . . ?
N1 C8 C9 C10 171(2) . . . . ?
C9' C8 C9 C10 96(8) . . . . ?
C8 C9 C10 C11 15(4) . . . . ?
N1 C8 C9' C10' 154.3(19) . . . . ?
C9 C8 C9' C10' -95(8) . . . . ?
C8 C9' C10' C11' 75(4) . . . . ?

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
C9' H9'2 I1 0.97 3.09 3.65(3) 118.2 .
C8 H8B I1 0.97 2.94 3.408(18) 110.8 .
C8 H8B I1 0.97 2.94 3.408(18) 110.8 .
C9' H9'2 I1 0.97 3.09 3.65(3) 118.2 .

_refine_diff_density_max         3.036
_refine_diff_density_min         -2.067
_refine_diff_density_rms         0.260

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v22040_0m
_database_code_depnum_ccdc_archive 'CCDC 2142800'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2022-01-18 deposited with the CCDC.	2023-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 I2 N2 O3 S'
_chemical_formula_weight         572.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.5550(4)
_cell_length_b                   8.3352(2)
_cell_length_c                   20.4748(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.3480(10)
_cell_angle_gamma                90
_cell_volume                     1901.66(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      5.305
_cell_measurement_theta_max      54.986

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    3.434
_shelx_estimated_absorpt_T_min   0.547
_shelx_estimated_absorpt_T_max   0.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4144
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18606
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.652
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3710
_reflns_number_gt                3420
_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-2013 (Sheldrick, 2013)'
_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)+(0.0222P)²+2.1135P] 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         3710
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0587
_refine_ls_wR_factor_gt          0.0571
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.010
_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 0.81159(2) 0.93184(2) 0.69684(2) 0.03905(7) Uani 1 1 d . . . . .
I2 I 0.92537(2) 0.76911(3) 0.96347(2) 0.05807(9) Uani 1 1 d . . . . .
S1 S 0.52610(7) 0.60023(9) 0.65045(4) 0.03737(17) Uani 1 1 d . . . . .
O1 O 0.8781(2) 0.2884(2) 0.69505(12) 0.0406(5) Uani 1 1 d . . . . .
O2 O 0.5521(2) 0.7564(3) 0.62933(12) 0.0471(6) Uani 1 1 d . . . . .
O3 O 0.4059(2) 0.5590(3) 0.65039(13) 0.0541(6) Uani 1 1 d . . . . .
N1 N 0.7817(2) 0.4410(3) 0.75819(12) 0.0292(5) Uani 1 1 d . . . . .
N2 N 0.6032(2) 0.5826(3) 0.73143(12) 0.0333(5) Uani 1 1 d . . . . .
C1 C 0.8468(2) 0.4174(3) 0.71235(14) 0.0284(6) Uani 1 1 d . . . . .
C2 C 0.8705(2) 0.5800(3) 0.68790(13) 0.0274(6) Uani 1 1 d . . . . .
C3 C 0.8028(2) 0.6851(3) 0.70946(13) 0.0266(6) Uani 1 1 d . . . . .
C4 C 0.7365(2) 0.6054(3) 0.75527(13) 0.0272(5) Uani 1 1 d . . . . .
C5 C 0.5823(3) 0.4301(4) 0.76521(18) 0.0435(8) Uani 1 1 d . . . . .
H5A H 0.5120 0.3751 0.7380 0.052 Uiso 1 1 calc R U . . .
H5B H 0.5703 0.4524 0.8094 0.052 Uiso 1 1 calc R U . . .
C6 C 0.6947(3) 0.3272(4) 0.77208(18) 0.0426(7) Uani 1 1 d . . . . .
H6A H 0.7226 0.2830 0.8173 0.051 Uiso 1 1 calc R U . . .
H6B H 0.6794 0.2402 0.7395 0.051 Uiso 1 1 calc R U . . .
C7 C 0.9540(3) 0.6048(4) 0.64444(16) 0.0389(7) Uani 1 1 d . . . . .
H7A H 1.0353 0.5945 0.6715 0.058 Uiso 1 1 calc R U . . .
H7B H 0.9421 0.7101 0.6248 0.058 Uiso 1 1 calc R U . . .
H7C H 0.9384 0.5258 0.6091 0.058 Uiso 1 1 calc R U . . .
C8 C 0.7631(3) 0.6824(4) 0.82618(14) 0.0335(6) Uani 1 1 d . . . . .
H8A H 0.7425 0.7954 0.8215 0.040 Uiso 1 1 calc R U . . .
H8B H 0.7133 0.6320 0.8517 0.040 Uiso 1 1 calc R U . . .
C9 C 0.8930(3) 0.6650(4) 0.86453(15) 0.0429(8) Uani 1 1 d . . . . .
H9A H 0.9431 0.7176 0.8397 0.051 Uiso 1 1 calc R U . . .
H9B H 0.9144 0.5523 0.8686 0.051 Uiso 1 1 calc R U . . .
C10 C 0.5762(3) 0.4564(4) 0.60097(15) 0.0360(7) Uani 1 1 d . . . . .
C11 C 0.5403(3) 0.2980(4) 0.60178(18) 0.0464(8) Uani 1 1 d . . . . .
H11 H 0.4872 0.2683 0.6267 0.056 Uiso 1 1 calc R U . . .
C12 C 0.5842(3) 0.1841(4) 0.56516(19) 0.0507(9) Uani 1 1 d . . . . .
H12 H 0.5623 0.0771 0.5668 0.061 Uiso 1 1 calc R U . . .
C13 C 0.6598(3) 0.2279(5) 0.52642(18) 0.0493(9) Uani 1 1 d . . . . .
C14 C 0.6912(3) 0.3873(5) 0.52400(16) 0.0474(8) Uani 1 1 d . . . . .
H14 H 0.7410 0.4174 0.4971 0.057 Uiso 1 1 calc R U . . .
C15 C 0.6498(3) 0.5034(4) 0.56076(15) 0.0403(7) Uani 1 1 d . . . . .
H15 H 0.6710 0.6105 0.5585 0.048 Uiso 1 1 calc R U . . .
C16 C 0.7076(4) 0.1029(6) 0.4867(2) 0.0747(13) Uani 1 1 d . . . . .
H16A H 0.6422 0.0580 0.4524 0.112 Uiso 1 1 calc R U . . .
H16B H 0.7470 0.0194 0.5167 0.112 Uiso 1 1 calc R U . . .
H16C H 0.7638 0.1520 0.4657 0.112 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 C3 2.079(3) . ?
I2 C9 2.144(3) . ?
S1 O2 1.429(2) . ?
S1 O3 1.431(2) . ?
S1 N2 1.668(3) . ?
S1 C10 1.764(3) . ?
O1 C1 1.217(3) . ?
N1 C1 1.363(4) . ?
N1 C4 1.463(3) . ?
N1 C6 1.464(4) . ?
N2 C5 1.497(4) . ?
N2 C4 1.499(4) . ?
C1 C2 1.495(4) . ?
C2 C3 1.326(4) . ?
C2 C7 1.490(4) . ?
C3 C4 1.513(4) . ?
C4 C8 1.542(4) . ?
C5 C6 1.531(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.506(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.385(5) . ?
C10 C15 1.388(4) . ?
C11 C12 1.387(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(5) . ?
C13 C16 1.513(5) . ?
C14 C15 1.386(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 O3 120.05(15) . . ?
O2 S1 N2 106.34(13) . . ?
O3 S1 N2 104.04(14) . . ?
O2 S1 C10 108.57(15) . . ?
O3 S1 C10 107.60(15) . . ?
N2 S1 C10 109.94(13) . . ?
C1 N1 C4 111.3(2) . . ?
C1 N1 C6 125.0(2) . . ?
C4 N1 C6 111.0(2) . . ?
C5 N2 C4 103.5(2) . . ?
C5 N2 S1 115.2(2) . . ?
C4 N2 S1 123.00(18) . . ?
O1 C1 N1 126.1(3) . . ?
O1 C1 C2 127.5(3) . . ?
N1 C1 C2 106.4(2) . . ?
C3 C2 C7 129.8(3) . . ?
C3 C2 C1 108.1(2) . . ?
C7 C2 C1 122.1(2) . . ?
C2 C3 C4 110.9(2) . . ?
C2 C3 I1 124.0(2) . . ?
C4 C3 I1 124.11(18) . . ?
N1 C4 N2 102.7(2) . . ?
N1 C4 C3 101.7(2) . . ?
N2 C4 C3 119.9(2) . . ?
N1 C4 C8 111.8(2) . . ?
N2 C4 C8 106.9(2) . . ?
C3 C4 C8 113.2(2) . . ?
N2 C5 C6 106.4(2) . . ?
N2 C5 H5A 110.5 . . ?
C6 C5 H5A 110.5 . . ?
N2 C5 H5B 110.5 . . ?
C6 C5 H5B 110.5 . . ?
H5A C5 H5B 108.6 . . ?
N1 C6 C5 103.2(2) . . ?
N1 C6 H6A 111.1 . . ?
C5 C6 H6A 111.1 . . ?
N1 C6 H6B 111.1 . . ?
C5 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C4 112.0(2) . . ?
C9 C8 H8A 109.2 . . ?
C4 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C4 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 I2 110.7(2) . . ?
C8 C9 H9A 109.5 . . ?
I2 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
I2 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C15 120.6(3) . . ?
C11 C10 S1 119.7(3) . . ?
C15 C10 S1 119.7(2) . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 C16 120.3(4) . . ?
C14 C13 C16 120.4(4) . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 118.6(3) . . ?
C14 C15 H15 120.7 . . ?
C10 C15 H15 120.7 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O2 S1 N2 C5 176.2(2) . . . . ?
O3 S1 N2 C5 48.5(2) . . . . ?
C10 S1 N2 C5 -66.5(2) . . . . ?
O2 S1 N2 C4 -56.0(2) . . . . ?
O3 S1 N2 C4 176.4(2) . . . . ?
C10 S1 N2 C4 61.4(2) . . . . ?
C4 N1 C1 O1 -166.7(3) . . . . ?
C6 N1 C1 O1 -28.9(5) . . . . ?
C4 N1 C1 C2 12.9(3) . . . . ?
C6 N1 C1 C2 150.8(3) . . . . ?
O1 C1 C2 C3 168.5(3) . . . . ?
N1 C1 C2 C3 -11.2(3) . . . . ?
O1 C1 C2 C7 -9.2(5) . . . . ?
N1 C1 C2 C7 171.2(3) . . . . ?
C7 C2 C3 C4 -177.5(3) . . . . ?
C1 C2 C3 C4 5.1(3) . . . . ?
C7 C2 C3 I1 -8.2(4) . . . . ?
C1 C2 C3 I1 174.43(18) . . . . ?
C1 N1 C4 N2 115.0(2) . . . . ?
C6 N1 C4 N2 -29.0(3) . . . . ?
C1 N1 C4 C3 -9.7(3) . . . . ?
C6 N1 C4 C3 -153.6(2) . . . . ?
C1 N1 C4 C8 -130.7(3) . . . . ?
C6 N1 C4 C8 85.3(3) . . . . ?
C5 N2 C4 N1 36.1(3) . . . . ?
S1 N2 C4 N1 -96.6(2) . . . . ?
C5 N2 C4 C3 147.7(2) . . . . ?
S1 N2 C4 C3 15.0(3) . . . . ?
C5 N2 C4 C8 -81.7(3) . . . . ?
S1 N2 C4 C8 145.6(2) . . . . ?
C2 C3 C4 N1 2.3(3) . . . . ?
I1 C3 C4 N1 -167.01(18) . . . . ?
C2 C3 C4 N2 -109.9(3) . . . . ?
I1 C3 C4 N2 80.8(3) . . . . ?
C2 C3 C4 C8 122.4(3) . . . . ?
I1 C3 C4 C8 -47.0(3) . . . . ?
C4 N2 C5 C6 -31.2(3) . . . . ?
S1 N2 C5 C6 105.9(3) . . . . ?
C1 N1 C6 C5 -128.4(3) . . . . ?
C4 N1 C6 C5 9.6(3) . . . . ?
N2 C5 C6 N1 13.7(3) . . . . ?
N1 C4 C8 C9 50.6(3) . . . . ?
N2 C4 C8 C9 162.3(2) . . . . ?
C3 C4 C8 C9 -63.5(3) . . . . ?
C4 C8 C9 I2 -178.81(19) . . . . ?
O2 S1 C10 C11 -166.9(3) . . . . ?
O3 S1 C10 C11 -35.6(3) . . . . ?
N2 S1 C10 C11 77.1(3) . . . . ?
O2 S1 C10 C15 12.1(3) . . . . ?
O3 S1 C10 C15 143.4(3) . . . . ?
N2 S1 C10 C15 -103.9(3) . . . . ?
C15 C10 C11 C12 3.8(5) . . . . ?
S1 C10 C11 C12 -177.2(3) . . . . ?
C10 C11 C12 C13 -2.1(5) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C11 C12 C13 C16 179.9(4) . . . . ?
C12 C13 C14 C15 1.3(5) . . . . ?
C16 C13 C14 C15 -179.1(3) . . . . ?
C13 C14 C15 C10 0.4(5) . . . . ?
C11 C10 C15 C14 -3.0(5) . . . . ?
S1 C10 C15 C14 178.0(2) . . . . ?

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
C9 H9A O1 0.97 2.43 3.353(4) 159.2 2_756
C6 H6B I1 0.97 3.23 4.020(3) 140.3 1_545
C6 H6A O3 0.97 2.58 3.138(4) 116.9 2_646
C9 H9A O1 0.97 2.43 3.353(4) 159.2 2_756
C6 H6B I1 0.97 3.23 4.020(3) 140.3 1_545
C6 H6A O3 0.97 2.58 3.138(4) 116.9 2_646
C6 H6A O3 0.97 2.58 3.138(4) 116.9 2_646
C6 H6B I1 0.97 3.23 4.020(3) 140.3 1_545
C9 H9A O1 0.97 2.43 3.353(4) 159.2 2_756

_refine_diff_density_max         0.567
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4

