# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2000276'
loop_
_audit_author_name
_audit_author_address
'Daniil Ivanov'
;SPbSU
Russia
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT431_3                   
;
PROBLEM: Short Inter HL..A Contact  I1       ..S1A      .       3.22 Ang.  
RESPONSE: The contacts are due to the C-I...X halogen bonding.
;
# end Validation Reply Form

_audit_creation_date             2019-09-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 I, C N S'
_chemical_formula_sum            'C13 H10 I N S'
_chemical_formula_weight         339.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N1 I1 C14 H10'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.5458(5)
_cell_length_b                   11.1302(8)
_cell_length_c                   15.0196(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.316(6)
_cell_angle_gamma                90
_cell_volume                     1261.11(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3618
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.0180
_cell_measurement_theta_min      3.0010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7469
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.206
_diffrn_reflns_theta_min         2.713
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   26.00   96.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686   77.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega   44.00   86.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686  178.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega    5.00   85.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686   57.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
  4 omega   38.00   92.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686  178.0000  120.0000 54
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0112872000
_diffrn_orient_matrix_UB_12      -0.0259844000
_diffrn_orient_matrix_UB_13      0.0428104000
_diffrn_orient_matrix_UB_21      0.0932832000
_diffrn_orient_matrix_UB_22      0.0053189000
_diffrn_orient_matrix_UB_23      -0.0034370000
_diffrn_orient_matrix_UB_31      -0.0034127000
_diffrn_orient_matrix_UB_32      0.0580158000
_diffrn_orient_matrix_UB_33      0.0195500000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3349
_reflns_number_total             3991
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3991
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0123P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0496
_refine_ls_wR_factor_ref         0.0541
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C2(H2), C12(H12), C10(H10), C11(H11), C6(H6), C3(H3), C5(H5),
 C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.70967(2) 0.83677(2) 0.42052(2) 0.01256(5) Uani 1 1 d . . . . .
S1A S 1.33104(9) 0.88539(6) 0.63578(4) 0.01802(13) Uani 1 1 d . . . . .
N1A N 1.0045(3) 0.8478(2) 0.54648(14) 0.0203(5) Uani 1 1 d . . . . .
C7 C 0.4643(3) 0.8234(2) 0.35102(14) 0.0120(5) Uani 1 1 d . . . . .
C8 C 0.3309(3) 0.9006(2) 0.37718(15) 0.0144(5) Uani 1 1 d . . . . .
H8 H 0.3506 0.9557 0.4229 0.017 Uiso 1 1 calc R . . . .
C1A C 1.1382(3) 0.8624(2) 0.58312(15) 0.0144(5) Uani 1 1 d . . . . .
C9 C 0.1675(3) 0.8935(2) 0.33352(15) 0.0149(5) Uani 1 1 d . . . . .
H9 H 0.0766 0.9454 0.3490 0.018 Uiso 1 1 calc R . . . .
C1 C 0.7287(3) 0.6538(2) 0.45563(16) 0.0140(5) Uani 1 1 d . . . . .
C2 C 0.6743(3) 0.6211(2) 0.53940(16) 0.0163(5) Uani 1 1 d . . . . .
H2 H 0.6239 0.6772 0.5771 0.020 Uiso 1 1 calc R . . . .
C12 C 0.4407(3) 0.7405(2) 0.28361(15) 0.0158(5) Uani 1 1 d . . . . .
H12 H 0.5332 0.6912 0.2664 0.019 Uiso 1 1 calc R . . . .
C10 C 0.1393(3) 0.8093(2) 0.26709(16) 0.0171(5) Uani 1 1 d . . . . .
H10 H 0.0287 0.8038 0.2388 0.021 Uiso 1 1 calc R . . . .
C11 C 0.2748(3) 0.7329(3) 0.24227(16) 0.0191(5) Uani 1 1 d . . . . .
H11 H 0.2543 0.6763 0.1977 0.023 Uiso 1 1 calc R . . . .
C6 C 0.8014(3) 0.5721(2) 0.39687(16) 0.0180(5) Uani 1 1 d . . . . .
H6 H 0.8370 0.5963 0.3408 0.022 Uiso 1 1 calc R . . . .
C3 C 0.6966(3) 0.5033(3) 0.56572(17) 0.0210(6) Uani 1 1 d . . . . .
H3 H 0.6629 0.4797 0.6223 0.025 Uiso 1 1 calc R . . . .
C5 C 0.8195(3) 0.4538(3) 0.42407(17) 0.0212(6) Uani 1 1 d . . . . .
H5 H 0.8659 0.3971 0.3855 0.025 Uiso 1 1 calc R . . . .
C4 C 0.7688(3) 0.4194(3) 0.50853(17) 0.0216(6) Uani 1 1 d . . . . .
H4 H 0.7832 0.3402 0.5269 0.026 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.109(2) . ?
I1 C1 2.107(3) . ?
S1A C1A 1.660(3) . ?
N1A C1A 1.150(3) . ?
C7 C8 1.387(3) . ?
C7 C12 1.378(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.389(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.387(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(4) . ?
C11 H11 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.385(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.387(4) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 I1 C7 96.30(10) . . ?
C8 C7 I1 116.79(18) . . ?
C12 C7 I1 120.52(18) . . ?
C12 C7 C8 122.7(2) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.3(2) . . ?
C9 C8 H8 120.8 . . ?
N1A C1A S1A 179.3(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C2 C1 I1 117.57(19) . . ?
C2 C1 C6 122.4(2) . . ?
C6 C1 I1 119.94(18) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C7 C12 H12 121.0 . . ?
C7 C12 C11 118.0(2) . . ?
C11 C12 H12 121.0 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C1 C6 H6 120.9 . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 H6 120.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2000280'
loop_
_audit_author_name
_audit_author_address
'Daniil Ivanov'
;SPbSU
Russia
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT431_7                   
;
PROBLEM: Short Inter HL..A Contact  I1       ..S1A      .       3.19 Ang.  
RESPONSE: The contacts are due to the C-I...X halogen bonding.
;
# end Validation Reply Form

_audit_creation_date             2019-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H20 I O3, C N S'
_chemical_formula_sum            'C18 H20 I N O3 S'
_chemical_formula_weight         457.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C36  N2  O6  S2  I2  H1  '
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'
I I -0.3257 6.8362 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.68740(10)
_cell_length_b                   9.16050(10)
_cell_length_c                   11.76420(10)
_cell_angle_alpha                95.5680(10)
_cell_angle_beta                 93.4270(10)
_cell_angle_gamma                99.6570(10)
_cell_volume                     915.821(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11083
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.5350
_cell_measurement_theta_min      3.7740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.934
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 5 2 0.0904
4 3 0 0.0868
-2 -5 -1 0.0721
-5 1 2 0.0737
4 -4 -3 0.0982
-3 1 -6 0.0790
3 4 -3 0.0959
-2 -4 5 0.0822
3 0 6 0.0590

_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.142
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.5439 5.3242 1.9803 -0.6619 0.1586 -0.7327
4.3905 2.8849 -0.4154 0.0790 -0.0190 -0.9967
-1.7565 -4.9717 -1.3955 0.4846 -0.1161 0.8670
-5.4467 1.0156 2.3949 -0.7193 0.1725 0.6729
3.5806 -4.3616 -3.0855 0.9724 -0.2331 0.0107
-3.0560 0.7181 -6.1419 -0.2075 -0.8658 0.4554
3.2417 3.9611 -2.9250 -0.0928 -0.3864 -0.9177
-2.2485 -4.0717 4.6756 0.1521 0.6338 0.7584
3.2325 -0.4775 5.9327 0.2008 0.8379 -0.5076

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11872
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        64.996
_diffrn_reflns_theta_max         64.996
_diffrn_reflns_theta_min         3.787
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  28.00   0.50    0.05    --  -47.20  19.00 -30.00  106
  2  ω     59.00  97.00   0.50    0.05    --   47.20 150.00 -54.00   76
  3  ω     77.00 120.00   0.50    0.05    --   47.20 125.00   0.00   86
  4  ω     95.00 122.00   0.50    0.05    --  107.75 150.00 -54.00   54
  5  ω    127.00 175.00   0.50    0.05    --  107.75 122.00 143.00   96
  6  ω     94.00 166.00   0.50    0.05    --  107.75  15.00  30.00  144
  7  ω     74.00 102.00   0.50    0.05    --  107.75 -94.00 120.00   56
  8  ω     77.00 107.00   0.50    0.05    --  107.75-122.00  62.00   60
  9  ω     69.00  95.00   0.50    0.05    --  107.75 -94.00  90.00   52
 10  ω     45.00  71.00   0.50    0.05    --  107.75 -61.00  90.00   52
 11  ω     42.00  67.00   0.50    0.05    --  107.75 -61.00 120.00   50
 12  ω     39.00  71.00   0.50    0.05    --  107.75 -94.00 120.00   64
 13  ω     37.00  63.00   0.50    0.05    --  107.75 -94.00  90.00   52
 14  ω     36.00 104.00   0.50    0.05    --  107.75 -77.00  30.00  136
 15  ω     73.00  98.00   0.50    0.05    --  107.75-125.00   0.00   50
 16  ω     75.00 127.00   0.50    0.05    --  107.75-150.00 -99.00  104
 17  ω     84.00 111.00   0.50    0.05    --  107.75-125.00 -90.00   54
 18  ω     52.00  77.00   0.50    0.05    --  107.75-125.00 -90.00   50
 19  ω     37.00  77.00   0.50    0.05    --  107.75 -77.00 -60.00   80
 20  ω     35.00 112.00   0.50    0.05    --  107.75-125.00 -60.00  154
 21  ω     68.00  93.00   0.50    0.05    --   47.20-150.00 -99.00   50
 22  ω     36.00  66.00   0.50    0.05    --  107.75 -61.00  30.00   60
 23  ω     27.00  91.00   0.50    0.05    --   47.20-122.00  62.00  128
 24  ω     35.00  60.00   0.50    0.05    --  107.75 -61.00 -90.00   50
 25  ω     36.00  69.00   0.50    0.05    --  107.75 -61.00-150.00   66
 26  ω     38.00  69.00   0.50    0.05    --  107.75 -61.00-180.00   62
 27  ω    -17.00  16.00   0.50    0.05    --   47.20 -19.00 -60.00   66
 28  ω    -27.00  12.00   0.50    0.05    --   47.20 -19.00 -90.00   78
 29  ω    -93.00 -36.00   0.50    0.05    --  -47.20 122.00 143.00  114
 30  ω    -18.00  25.00   0.50    0.05    --   47.20 -19.00 150.00   86
 31  ω    -99.00 -68.00   0.50    0.05    --  -47.20 150.00 -54.00   62
 32  ω   -105.00 -80.00   0.50    0.05    -- -106.00 150.00 -54.00   50
 33  ω   -111.00 -49.00   0.50    0.05    -- -106.00 125.00 -60.00  124
 34  ω    -62.00 -34.00   0.50    0.05    -- -106.00 112.00-126.97   56
 35  ω    -96.00 -37.00   0.50    0.05    -- -106.00  77.00 -30.00  118
 36  ω    -82.00 -57.00   0.50    0.05    -- -106.00 145.00  -3.31   50
 37  ω   -110.00 -85.00   0.50    0.05    -- -106.00 125.00  30.00   50
 38  ω   -126.00 -90.00   0.50    0.05    -- -106.00 145.00  -3.31   72
 39  ω   -117.00 -53.00   0.50    0.05    -- -106.00 133.00 -51.98  128
 40  ω   -108.00 -83.00   0.50    0.05    -- -106.00 112.00-126.97   50
 41  ω   -151.00 -35.00   0.50    0.05    -- -106.00   0.00-120.00  232
 42  ω   -106.00 -56.00   0.50    0.05    --  -47.20-150.00 -99.00  100
 43  ω   -113.00 -82.00   0.50    0.05    -- -106.00-150.00 -99.00   62
 44  ω   -144.00-119.00   0.50    0.05    -- -106.00-122.00  62.00   50
 45  ω   -127.00 -96.00   0.50    0.05    -- -106.00 -45.00 150.00   62
 46  ω   -177.00-132.00   0.50    0.05    -- -106.00 -45.00 150.00   90
 47  ω   -177.00 -98.00   0.50    0.05    -- -106.00 -45.00  90.00  158
 48  ω   -175.00 -95.00   0.50    0.05    -- -106.00 -30.00 120.00  160
 49  ω   -109.00 -78.00   0.50    0.05    -- -106.00 122.00 143.00   62
 50  ω    -88.00 -39.00   0.50    0.05    -- -106.00 125.00 120.00   98
 51  ω     25.00  56.00   0.50    0.05    --   47.20  77.00 -90.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0964388000
_diffrn_orient_matrix_UB_12      -0.1235093000
_diffrn_orient_matrix_UB_13      -0.0286449000
_diffrn_orient_matrix_UB_21      0.0209598000
_diffrn_orient_matrix_UB_22      -0.0200315000
_diffrn_orient_matrix_UB_23      0.1281952000
_diffrn_orient_matrix_UB_31      -0.1510410000
_diffrn_orient_matrix_UB_32      -0.1174487000
_diffrn_orient_matrix_UB_33      -0.0127191000
_diffrn_oxdiff_digest_frames     
;
01a58dc302b7a2a3b25aa4426fa1e3ded6044243b09
;
_diffrn_oxdiff_digest_hkl        
;
019799d632cc1a71c0a0b73f605c5d22274791
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3073
_reflns_number_total             3114
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.156
_refine_diff_density_min         -2.042
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+0.9014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0889
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C7)
Uanis(C15) = Uanis(C13)
Uanis(C11) = Uanis(C9)
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C2(H2), C4(H4), C6(H6)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C17(H17A,H17B,
 H17C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.17041(2) 0.37603(2) 0.18822(2) 0.00581(12) Uani 1 1 d . . . . .
S1A S 0.04044(11) 0.82758(10) 0.01798(8) 0.0147(2) Uani 1 1 d . . . . .
O1 O 0.1239(3) 0.0811(3) 0.3016(2) 0.0099(5) Uani 1 1 d . . . . .
O2 O 0.5695(3) -0.1231(3) 0.2010(3) 0.0185(6) Uani 1 1 d . . . . .
O3 O 0.4926(3) 0.3575(3) 0.0959(2) 0.0133(6) Uani 1 1 d . . . . .
N1A N -0.0025(4) 0.6032(4) 0.1657(3) 0.0193(8) Uani 1 1 d . . . . .
C7 C 0.3123(4) 0.2146(4) 0.1990(3) 0.0082(5) Uani 1 1 d . . . . .
C9 C 0.3517(4) -0.0243(4) 0.2517(3) 0.0104(5) Uani 1 1 d . . . . .
H9 H 0.3199 -0.1090 0.2878 0.012 Uiso 1 1 calc R . . . .
C12 C 0.4531(4) 0.2305(4) 0.1455(3) 0.0082(7) Uani 1 1 d . . . . .
C11 C 0.5440(4) 0.1192(4) 0.1443(3) 0.0104(5) Uani 1 1 d . . . . .
H11 H 0.6376 0.1290 0.1090 0.012 Uiso 1 1 calc R . . . .
C8 C 0.2616(4) 0.0855(4) 0.2515(3) 0.0074(7) Uani 1 1 d . . . . .
C1 C 0.2888(4) 0.5265(4) 0.3301(3) 0.0082(5) Uani 1 1 d . . . . .
C2 C 0.1980(4) 0.5761(4) 0.4120(3) 0.0113(8) Uani 1 1 d . . . . .
H2 H 0.0901 0.5445 0.4059 0.014 Uiso 1 1 calc R . . . .
C10 C 0.4910(4) -0.0079(4) 0.1975(3) 0.0103(7) Uani 1 1 d . . . . .
C1A C 0.0168(5) 0.6924(5) 0.1026(3) 0.0141(8) Uani 1 1 d . . . . .
C13 C 0.0710(5) -0.0485(4) 0.3574(4) 0.0160(6) Uani 1 1 d . . . . .
H13A H 0.0564 -0.1355 0.3028 0.024 Uiso 1 1 calc GR . . . .
H13B H -0.0264 -0.0396 0.3895 0.024 Uiso 1 1 calc GR . . . .
H13C H 0.1478 -0.0572 0.4174 0.024 Uiso 1 1 calc GR . . . .
C5 C 0.5231(5) 0.6704(4) 0.4249(4) 0.0155(8) Uani 1 1 d . . . . .
C3 C 0.2713(5) 0.6751(4) 0.5050(3) 0.0140(8) Uani 1 1 d . . . . .
C4 C 0.4333(5) 0.7202(4) 0.5095(3) 0.0148(8) Uani 1 1 d . . . . .
H4 H 0.4829 0.7858 0.5713 0.018 Uiso 1 1 calc R . . . .
C15 C 0.6393(5) 0.3810(5) 0.0435(4) 0.0160(6) Uani 1 1 d . . . . .
H15A H 0.6397 0.3019 -0.0163 0.024 Uiso 1 1 calc GR . . . .
H15B H 0.7238 0.3822 0.1002 0.024 Uiso 1 1 calc GR . . . .
H15C H 0.6521 0.4745 0.0117 0.024 Uiso 1 1 calc GR . . . .
C6 C 0.4489(4) 0.5711(4) 0.3329(3) 0.0107(7) Uani 1 1 d . . . . .
H6 H 0.5059 0.5358 0.2750 0.013 Uiso 1 1 calc R . . . .
C14 C 0.7123(5) -0.1164(5) 0.1453(4) 0.0174(9) Uani 1 1 d . . . . .
H14A H 0.6932 -0.1002 0.0666 0.026 Uiso 1 1 calc GR . . . .
H14B H 0.7503 -0.2085 0.1488 0.026 Uiso 1 1 calc GR . . . .
H14C H 0.7890 -0.0359 0.1830 0.026 Uiso 1 1 calc GR . . . .
C17 C 0.6971(5) 0.7264(5) 0.4303(4) 0.0215(9) Uani 1 1 d . . . . .
H17A H 0.7161 0.8220 0.4019 0.032 Uiso 1 1 calc GR . . . .
H17B H 0.7457 0.6575 0.3843 0.032 Uiso 1 1 calc GR . . . .
H17C H 0.7401 0.7354 0.5083 0.032 Uiso 1 1 calc GR . . . .
C16 C 0.1778(5) 0.7279(5) 0.5993(4) 0.0227(10) Uani 1 1 d . . . . .
H16A H 0.0744 0.7332 0.5683 0.034 Uiso 1 1 calc GR . . . .
H16B H 0.2283 0.8248 0.6336 0.034 Uiso 1 1 calc GR . . . .
H16C H 0.1710 0.6594 0.6564 0.034 Uiso 1 1 calc GR . . . .


_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 C7 2.086(4) . ?
I1 C1 2.149(3) . ?
S1A C1A 1.657(4) . ?
O1 C8 1.362(5) . ?
O1 C13 1.435(4) . ?
O2 C10 1.352(5) . ?
O2 C14 1.433(5) . ?
O3 C12 1.354(5) . ?
O3 C15 1.442(5) . ?
N1A C1A 1.155(6) . ?
C7 C12 1.401(5) . ?
C7 C8 1.405(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.374(6) . ?
C9 C10 1.394(5) . ?
C12 C11 1.390(6) . ?
C11 H11 0.9300 . ?
C11 C10 1.398(5) . ?
C1 C2 1.373(5) . ?
C1 C6 1.380(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C5 C4 1.390(6) . ?
C5 C6 1.394(6) . ?
C5 C17 1.508(5) . ?
C3 C4 1.395(6) . ?
C3 C16 1.504(6) . ?
C4 H4 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C6 H6 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
C7 I1 C1 96.37(14) . . ?
C8 O1 C13 116.6(3) . . ?
C10 O2 C14 118.4(3) . . ?
C12 O3 C15 118.3(3) . . ?
C12 C7 I1 119.3(3) . . ?
C12 C7 C8 120.2(3) . . ?
C8 C7 I1 120.3(3) . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
O3 C12 C7 116.4(3) . . ?
O3 C12 C11 123.2(3) . . ?
C11 C12 C7 120.3(3) . . ?
C12 C11 H11 120.8 . . ?
C12 C11 C10 118.3(3) . . ?
C10 C11 H11 120.8 . . ?
O1 C8 C7 115.6(3) . . ?
O1 C8 C9 124.6(3) . . ?
C9 C8 C7 119.8(3) . . ?
C2 C1 I1 117.1(3) . . ?
C2 C1 C6 123.7(3) . . ?
C6 C1 I1 119.2(3) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.5(3) . . ?
C3 C2 H2 120.7 . . ?
O2 C10 C9 114.9(3) . . ?
O2 C10 C11 123.3(3) . . ?
C9 C10 C11 121.8(4) . . ?
N1A C1A S1A 176.4(4) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C5 C6 118.9(4) . . ?
C4 C5 C17 120.7(4) . . ?
C6 C5 C17 120.4(4) . . ?
C2 C3 C16 120.6(4) . . ?
C4 C3 C2 118.4(4) . . ?
C4 C3 C16 121.0(4) . . ?
C5 C4 C3 122.2(4) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C6 C5 118.3(4) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C16 H16A 109.5 . . ?
C3 C16 H16B 109.5 . . ?
C3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.630
_oxdiff_exptl_absorpt_empirical_full_min 0.579
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2000279'
loop_
_audit_author_name
_audit_author_address
'Daniil Ivanov'
;SPbSU
Russia
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT431_6                   
;
PROBLEM: Short Inter HL..A Contact  I1       ..S1A      .       3.21 Ang.  
RESPONSE: The contacts are due to the C-I...X halogen bonding.
;
# end Validation Reply Form

_audit_creation_date             2019-09-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 I O, C N S'
_chemical_formula_sum            'C16 H16 I N O S'
_chemical_formula_weight         397.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N1 I1 O1 C16 H16'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9702(4)
_cell_length_b                   9.5118(4)
_cell_length_c                   11.5477(5)
_cell_angle_alpha                102.282(4)
_cell_angle_beta                 90.743(4)
_cell_angle_gamma                107.413(4)
_cell_volume                     813.44(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8880
_cell_measurement_theta_min      3.1310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6571
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.687
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -42.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.2748  133.0000 -115.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega  -89.00  -32.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.2748  178.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega   61.00   93.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686   57.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega   15.00   88.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686 -133.0000  176.0000 73

#__ type_ start__ end____ width___ exp.time_
  5 omega  -35.00   44.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686  -57.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
  6 omega  -47.00   70.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686  -19.0000 -120.0000 117
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0405694000
_diffrn_orient_matrix_UB_12      0.0508192000
_diffrn_orient_matrix_UB_13      0.0542567000
_diffrn_orient_matrix_UB_21      -0.0540181000
_diffrn_orient_matrix_UB_22      -0.0496067000
_diffrn_orient_matrix_UB_23      0.0321664000
_diffrn_orient_matrix_UB_31      0.0647634000
_diffrn_orient_matrix_UB_32      -0.0373661000
_diffrn_orient_matrix_UB_33      0.0003333000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3470
_reflns_number_total             3730
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0236
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0187P)²+0.0124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0488
_refine_ls_wR_factor_ref         0.0500
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C8(H8), C12(H12), C6(H6), C2(H2), C4(H4)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.31541(2) 0.63937(2) 0.89219(2) 0.01216(5) Uani 1 1 d . . . . .
S1A S -0.40778(8) 0.29198(7) 0.82599(5) 0.01652(12) Uani 1 1 d . . . . .
O1 O 1.0875(2) 0.9884(2) 0.83112(16) 0.0221(4) Uani 1 1 d . . . . .
N1A N -0.0420(3) 0.4350(3) 0.84257(18) 0.0210(5) Uani 1 1 d . . . . .
C7 C 0.5773(3) 0.7732(3) 0.89164(19) 0.0128(5) Uani 1 1 d . . . . .
C1 C 0.2749(3) 0.5954(3) 0.7049(2) 0.0154(5) Uani 1 1 d . . . . .
C1A C -0.1924(3) 0.3761(3) 0.8341(2) 0.0146(5) Uani 1 1 d . . . . .
C9 C 0.7843(3) 0.9922(3) 0.8488(2) 0.0162(5) Uani 1 1 d . . . . .
H9 H 0.8101 1.0874 0.8320 0.019 Uiso 1 1 calc R . . . .
C10 C 0.9178(3) 0.9266(3) 0.8556(2) 0.0162(5) Uani 1 1 d . . . . .
C11 C 0.8819(3) 0.7876(3) 0.8863(2) 0.0176(5) Uani 1 1 d . . . . .
H11 H 0.9727 0.7470 0.8950 0.021 Uiso 1 1 calc R . . . .
C8 C 0.6133(3) 0.9148(3) 0.8670(2) 0.0160(5) Uani 1 1 d . . . . .
H8 H 0.5234 0.9577 0.8627 0.019 Uiso 1 1 calc R . . . .
C12 C 0.7108(3) 0.7097(3) 0.9038(2) 0.0165(5) Uani 1 1 d . . . . .
H12 H 0.6855 0.6160 0.9235 0.020 Uiso 1 1 calc R . . . .
C6 C 0.2937(3) 0.4627(3) 0.6389(2) 0.0179(5) Uani 1 1 d . . . . .
H6 H 0.3208 0.3935 0.6761 0.021 Uiso 1 1 calc R . . . .
C15 C 1.1238(3) 1.1190(3) 0.7819(3) 0.0263(6) Uani 1 1 d . . . . .
H15A H 1.0460 1.0971 0.7118 0.039 Uiso 1 1 calc GR . . . .
H15B H 1.2439 1.1465 0.7616 0.039 Uiso 1 1 calc GR . . . .
H15C H 1.1058 1.2014 0.8393 0.039 Uiso 1 1 calc GR . . . .
C2 C 0.2377(3) 0.7034(3) 0.6548(2) 0.0172(5) Uani 1 1 d . . . . .
H2 H 0.2253 0.7912 0.7024 0.021 Uiso 1 1 calc R . . . .
C3 C 0.2192(3) 0.6776(3) 0.5310(2) 0.0198(5) Uani 1 1 d . . . . .
C5 C 0.2711(3) 0.4345(3) 0.5148(2) 0.0204(5) Uani 1 1 d . . . . .
C4 C 0.2354(3) 0.5426(3) 0.4633(2) 0.0230(6) Uani 1 1 d . . . . .
H4 H 0.2217 0.5246 0.3808 0.028 Uiso 1 1 calc R . . . .
C14 C 0.2854(4) 0.2887(3) 0.4401(2) 0.0272(6) Uani 1 1 d . . . . .
H14A H 0.3399 0.2409 0.4881 0.041 Uiso 1 1 calc GR . . . .
H14B H 0.3558 0.3097 0.3753 0.041 Uiso 1 1 calc GR . . . .
H14C H 0.1697 0.2226 0.4093 0.041 Uiso 1 1 calc GR . . . .
C13 C 0.1845(4) 0.7945(3) 0.4721(2) 0.0281(6) Uani 1 1 d . . . . .
H13A H 0.1613 0.8726 0.5312 0.042 Uiso 1 1 calc GR . . . .
H13B H 0.0842 0.7475 0.4150 0.042 Uiso 1 1 calc GR . . . .
H13C H 0.2860 0.8379 0.4327 0.042 Uiso 1 1 calc GR . . . .


_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 C7 2.095(2) . ?
I1 C1 2.115(2) . ?
S1A C1A 1.654(3) . ?
O1 C10 1.364(3) . ?
O1 C15 1.429(3) . ?
N1A C1A 1.154(3) . ?
C7 C8 1.383(3) . ?
C7 C12 1.391(3) . ?
C1 C6 1.380(3) . ?
C1 C2 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.394(3) . ?
C9 C8 1.384(3) . ?
C10 C11 1.389(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(3) . ?
C8 H8 0.9300 . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.400(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C2 H2 0.9300 . ?
C2 C3 1.396(3) . ?
C3 C4 1.397(4) . ?
C3 C13 1.509(4) . ?
C5 C4 1.387(4) . ?
C5 C14 1.507(3) . ?
C4 H4 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C7 I1 C1 92.12(9) . . ?
C10 O1 C15 117.05(19) . . ?
C8 C7 I1 120.05(16) . . ?
C8 C7 C12 121.3(2) . . ?
C12 C7 I1 118.27(17) . . ?
C6 C1 I1 118.14(17) . . ?
C6 C1 C2 123.4(2) . . ?
C2 C1 I1 118.41(17) . . ?
N1A C1A S1A 178.4(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.7(2) . . ?
O1 C10 C9 124.2(2) . . ?
O1 C10 C11 115.3(2) . . ?
C11 C10 C9 120.4(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C7 C12 H12 120.4 . . ?
C11 C12 C7 119.1(2) . . ?
C11 C12 H12 120.4 . . ?
C1 C6 H6 120.8 . . ?
C1 C6 C5 118.4(2) . . ?
C5 C6 H6 120.8 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 C13 120.4(2) . . ?
C4 C3 C13 120.9(2) . . ?
C6 C5 C14 119.8(2) . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 C14 121.4(2) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.3(2) . . ?
C5 C4 H4 118.9 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2000277'
loop_
_audit_author_name
_audit_author_address
'Daniil Ivanov'
;SPbSU
Russia
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT431_4                   
;
PROBLEM: Short Inter HL..A Contact  I1       ..S1A      .       3.20 Ang.  
RESPONSE: The contacts are due to the C-I...X halogen bonding.
;
# end Validation Reply Form

_audit_creation_date             2019-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 I O3, C N S'
_chemical_formula_sum            'C16 H16 I N O3 S'
_chemical_formula_weight         429.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S C16 N I O3 H16'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9290(4)
_cell_length_b                   10.6799(5)
_cell_length_c                   10.9498(9)
_cell_angle_alpha                99.640(5)
_cell_angle_beta                 102.654(6)
_cell_angle_gamma                107.017(4)
_cell_volume                     838.04(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3649
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7390
_cell_measurement_theta_min      2.8440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9033
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.182
_diffrn_reflns_theta_min         2.802
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -61.00   1.0000    1.2300
omega____ theta____ kappa____ phi______ frames
    -      -25.4311 -178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   22.00   59.00   1.0000    1.2300
omega____ theta____ kappa____ phi______ frames
    -       26.5248  -99.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega   47.00   96.00   1.0000    1.2300
omega____ theta____ kappa____ phi______ frames
    -       26.5248 -178.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
  4 omega   43.00   68.00   1.0000    1.2300
omega____ theta____ kappa____ phi______ frames
    -       26.5248  -99.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   32.00   68.00   1.0000    1.2300
omega____ theta____ kappa____ phi______ frames
    -       26.5248  -99.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega   16.00   92.00   1.0000    1.2300
omega____ theta____ kappa____ phi______ frames
    -       26.5248   57.0000  -90.0000 76

#__ type_ start__ end____ width___ exp.time_
  7 omega  -37.00   34.00   1.0000    1.2300
omega____ theta____ kappa____ phi______ frames
    -       26.5248  -57.0000   30.0000 71

#__ type_ start__ end____ width___ exp.time_
  8 omega  -18.00   98.00   1.0000    1.2300
omega____ theta____ kappa____ phi______ frames
    -       26.5248   19.0000 -150.0000 116
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0293968000
_diffrn_orient_matrix_UB_12      -0.0315580000
_diffrn_orient_matrix_UB_13      -0.0496027000
_diffrn_orient_matrix_UB_21      0.0893592000
_diffrn_orient_matrix_UB_22      0.0492338000
_diffrn_orient_matrix_UB_23      0.0261600000
_diffrn_orient_matrix_UB_31      0.0259466000
_diffrn_orient_matrix_UB_32      -0.0414812000
_diffrn_orient_matrix_UB_33      0.0393929000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4728
_reflns_number_total             5289
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         5289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0183P)²+0.2886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0661
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C11(H11), C5(H5), C2(H2), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.35955(2) 0.20131(2) 0.64217(2) 0.01174(5) Uani 1 1 d . . . . .
S1A S -0.09975(9) -0.12428(7) 0.17549(7) 0.02173(14) Uani 1 1 d . . . . .
O2 O 0.9362(2) 0.41736(16) 1.17786(17) 0.0155(3) Uani 1 1 d . . . . .
O3 O 0.5480(2) 0.05894(15) 0.81765(19) 0.0175(4) Uani 1 1 d . . . . .
O1 O 0.5619(3) 0.49755(16) 0.80828(18) 0.0181(4) Uani 1 1 d . . . . .
N1A N 0.1417(3) 0.0939(2) 0.3815(2) 0.0207(5) Uani 1 1 d . . . . .
C1 C 0.5600(3) 0.2365(2) 0.5406(2) 0.0125(4) Uani 1 1 d . . . . .
C7 C 0.5534(3) 0.2792(2) 0.8217(2) 0.0114(4) Uani 1 1 d . . . . .
C6 C 0.6762(3) 0.1612(2) 0.5481(3) 0.0154(5) Uani 1 1 d . . . . .
H6 H 0.6650 0.0966 0.5960 0.019 Uiso 1 1 calc R . . . .
C9 C 0.7501(3) 0.4683(2) 1.0004(2) 0.0130(4) Uani 1 1 d . . . . .
H9 H 0.7940 0.5602 1.0405 0.016 Uiso 1 1 calc R . . . .
C8 C 0.6225(3) 0.4181(2) 0.8789(2) 0.0126(4) Uani 1 1 d . . . . .
C12 C 0.6186(3) 0.1905(2) 0.8835(2) 0.0126(4) Uani 1 1 d . . . . .
C11 C 0.7476(3) 0.2398(2) 1.0033(2) 0.0132(4) Uani 1 1 d . . . . .
H11 H 0.7917 0.1818 1.0449 0.016 Uiso 1 1 calc R . . . .
C1A C 0.0431(3) 0.0048(2) 0.2967(2) 0.0152(5) Uani 1 1 d . . . . .
C5 C 0.8095(3) 0.1844(2) 0.4827(3) 0.0178(5) Uani 1 1 d . . . . .
H5 H 0.8891 0.1354 0.4871 0.021 Uiso 1 1 calc R . . . .
C10 C 0.8107(3) 0.3782(2) 1.0607(2) 0.0118(4) Uani 1 1 d . . . . .
C14 C 1.0017(3) 0.5577(2) 1.2448(2) 0.0177(5) Uani 1 1 d . . . . .
H14A H 1.0649 0.6111 1.1956 0.026 Uiso 1 1 calc GR . . . .
H14B H 1.0845 0.5711 1.3281 0.026 Uiso 1 1 calc GR . . . .
H14C H 0.8993 0.5845 1.2556 0.026 Uiso 1 1 calc GR . . . .
C2 C 0.5727(4) 0.3329(2) 0.4698(3) 0.0178(5) Uani 1 1 d . . . . .
H2 H 0.4929 0.3819 0.4654 0.021 Uiso 1 1 calc R . . . .
C3 C 0.7073(4) 0.3550(3) 0.4056(3) 0.0221(5) Uani 1 1 d . . . . .
H3 H 0.7191 0.4203 0.3585 0.027 Uiso 1 1 calc R . . . .
C15 C 0.6222(4) -0.0344(2) 0.8703(3) 0.0198(5) Uani 1 1 d . . . . .
H15A H 0.5673 -0.1221 0.8112 0.030 Uiso 1 1 calc GR . . . .
H15B H 0.5961 -0.0396 0.9513 0.030 Uiso 1 1 calc GR . . . .
H15C H 0.7529 -0.0038 0.8838 0.030 Uiso 1 1 calc GR . . . .
C4 C 0.8243(4) 0.2803(3) 0.4111(3) 0.0211(5) Uani 1 1 d . . . . .
H4 H 0.9127 0.2946 0.3666 0.025 Uiso 1 1 calc R . . . .
C13 C 0.6500(4) 0.6414(2) 0.8602(3) 0.0232(6) Uani 1 1 d . . . . .
H13A H 0.6111 0.6875 0.7973 0.035 Uiso 1 1 calc GR . . . .
H13B H 0.7811 0.6637 0.8810 0.035 Uiso 1 1 calc GR . . . .
H13C H 0.6166 0.6687 0.9369 0.035 Uiso 1 1 calc GR . . . .


_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 2.114(2) . ?
I1 C7 2.073(2) . ?
S1A C1A 1.661(3) . ?
O2 C10 1.352(3) . ?
O2 C14 1.436(3) . ?
O3 C12 1.353(3) . ?
O3 C15 1.435(3) . ?
O1 C8 1.358(3) . ?
O1 C13 1.441(3) . ?
N1A C1A 1.153(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.382(3) . ?
C7 C8 1.399(3) . ?
C7 C12 1.404(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.389(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.391(3) . ?
C9 C10 1.392(3) . ?
C12 C11 1.382(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.395(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.384(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C4 H4 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C7 I1 C1 93.46(9) . . ?
C10 O2 C14 117.80(18) . . ?
C12 O3 C15 118.0(2) . . ?
C8 O1 C13 116.28(19) . . ?
C6 C1 I1 118.12(17) . . ?
C2 C1 I1 119.85(17) . . ?
C2 C1 C6 122.0(2) . . ?
C8 C7 I1 120.77(16) . . ?
C8 C7 C12 120.3(2) . . ?
C12 C7 I1 118.88(16) . . ?
C1 C6 H6 120.7 . . ?
C1 C6 C5 118.6(2) . . ?
C5 C6 H6 120.7 . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.6(2) . . ?
C10 C9 H9 120.7 . . ?
O1 C8 C7 116.4(2) . . ?
O1 C8 C9 123.5(2) . . ?
C9 C8 C7 120.0(2) . . ?
O3 C12 C7 115.6(2) . . ?
O3 C12 C11 124.4(2) . . ?
C11 C12 C7 120.0(2) . . ?
C12 C11 H11 120.6 . . ?
C12 C11 C10 118.9(2) . . ?
C10 C11 H11 120.6 . . ?
N1A C1A S1A 179.5(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
O2 C10 C9 123.0(2) . . ?
O2 C10 C11 114.8(2) . . ?
C9 C10 C11 122.2(2) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.5(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 2000281'
loop_
_audit_author_name
_audit_author_address
'Daniil Ivanov'
;SPbSU
Russia
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT431_8                   
;
PROBLEM: Short Inter HL..A Contact  I1       ..N1A      .       2.86 Ang.
RESPONSE: The contacts are due to the C-I...X halogen bonding.
;
# end Validation Reply Form

_audit_creation_date             2019-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 Cl I O3, C N S'
_chemical_formula_sum            'C16 H15 Cl I N O3 S'
_chemical_formula_weight         463.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N1 I1 Cl1 O1 C16 H15'
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4080(3)
_cell_length_b                   10.5039(4)
_cell_length_c                   11.2572(4)
_cell_angle_alpha                67.872(3)
_cell_angle_beta                 70.296(3)
_cell_angle_gamma                82.896(3)
_cell_volume                     867.04(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11994
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.0390
_cell_measurement_theta_min      2.9840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14517
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.741
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -94.00  -69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4311  -77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686   77.0000  -90.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686  -99.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega  -42.00   40.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686  -57.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686  -99.0000    0.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega   51.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686   57.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  7 omega  -54.00   43.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4311   77.0000 -120.0000 97

#__ type_ start__ end____ width___ exp.time_
  8 omega    4.00   42.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4311   38.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
  9 omega   47.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686   57.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
 10 omega   -2.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686   77.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
 11 omega    5.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686   57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 12 omega    5.00   30.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686   57.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega    9.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686   57.0000   90.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0265655000
_diffrn_orient_matrix_UB_12      -0.0275479000
_diffrn_orient_matrix_UB_13      -0.0522414000
_diffrn_orient_matrix_UB_21      -0.0605969000
_diffrn_orient_matrix_UB_22      -0.0535093000
_diffrn_orient_matrix_UB_23      0.0395845000
_diffrn_orient_matrix_UB_31      -0.0604309000
_diffrn_orient_matrix_UB_32      0.0411325000
_diffrn_orient_matrix_UB_33      -0.0290527000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3766
_reflns_number_total             3975
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3975
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0164
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0139P)²+0.3172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0374
_refine_ls_wR_factor_ref         0.0382
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C5(H5), C2(H2), C9(H9), C3(H3)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.61715(2) 0.47403(2) 0.62238(2) 0.01060(4) Uani 1 1 d . . . . .
Cl1 Cl 1.18881(6) 0.83576(4) 0.64113(5) 0.02142(10) Uani 1 1 d . . . . .
S1A S 0.89416(6) 0.77523(5) 0.08769(5) 0.01816(9) Uani 1 1 d . . . . .
O1 O 0.36166(14) 0.50425(12) 0.87538(11) 0.0131(2) Uani 1 1 d . . . . .
O3 O 0.77768(15) 0.19793(12) 0.75324(12) 0.0153(2) Uani 1 1 d . . . . .
O2 O 0.46678(16) 0.11206(12) 1.22538(12) 0.0170(3) Uani 1 1 d . . . . .
N1A N 0.67652(19) 0.66952(15) 0.35366(15) 0.0164(3) Uani 1 1 d . . . . .
C7 C 0.5706(2) 0.34781(16) 0.82299(16) 0.0109(3) Uani 1 1 d . . . . .
C12 C 0.6612(2) 0.22610(17) 0.85762(17) 0.0119(3) Uani 1 1 d . . . . .
C1 C 0.8066(2) 0.59085(17) 0.62059(16) 0.0118(3) Uani 1 1 d . . . . .
C8 C 0.4436(2) 0.38621(16) 0.92230(17) 0.0106(3) Uani 1 1 d . . . . .
C6 C 0.9402(2) 0.52296(17) 0.66446(17) 0.0140(3) Uani 1 1 d . . . . .
H6 H 0.9505 0.4280 0.6891 0.017 Uiso 1 1 calc R . . . .
C11 C 0.6295(2) 0.14258(17) 0.99287(17) 0.0124(3) Uani 1 1 d . . . . .
H11 H 0.6885 0.0612 1.0178 0.015 Uiso 1 1 calc R . . . .
C5 C 1.0582(2) 0.59984(17) 0.67081(17) 0.0147(3) Uani 1 1 d . . . . .
H5 H 1.1490 0.5570 0.7000 0.018 Uiso 1 1 calc R . . . .
C1A C 0.7676(2) 0.71394(17) 0.24262(18) 0.0133(3) Uani 1 1 d . . . . .
C10 C 0.5063(2) 0.18453(17) 1.09015(17) 0.0123(3) Uani 1 1 d . . . . .
C2 C 0.7865(2) 0.73181(17) 0.58329(17) 0.0148(3) Uani 1 1 d . . . . .
H2 H 0.6955 0.7746 0.5545 0.018 Uiso 1 1 calc R . . . .
C4 C 1.0390(2) 0.74081(17) 0.63315(17) 0.0145(3) Uani 1 1 d . . . . .
C9 C 0.4125(2) 0.30444(17) 1.05633(17) 0.0122(3) Uani 1 1 d . . . . .
H9 H 0.3300 0.3287 1.1234 0.015 Uiso 1 1 calc R . . . .
C3 C 0.9051(2) 0.80814(17) 0.58972(18) 0.0159(3) Uani 1 1 d . . . . .
H3 H 0.8947 0.9030 0.5652 0.019 Uiso 1 1 calc R . . . .
C13 C 0.2226(2) 0.54175(18) 0.97255(18) 0.0148(3) Uani 1 1 d . . . . .
H13A H 0.1709 0.6238 0.9268 0.022 Uiso 1 1 calc GR . . . .
H13B H 0.2632 0.5579 1.0358 0.022 Uiso 1 1 calc GR . . . .
H13C H 0.1410 0.4686 1.0199 0.022 Uiso 1 1 calc GR . . . .
C15 C 0.8642(2) 0.06836(17) 0.78380(18) 0.0171(4) Uani 1 1 d . . . . .
H15A H 0.9396 0.0597 0.7015 0.026 Uiso 1 1 calc GR . . . .
H15B H 0.7831 -0.0052 0.8284 0.026 Uiso 1 1 calc GR . . . .
H15C H 0.9276 0.0641 0.8419 0.026 Uiso 1 1 calc GR . . . .
C14 C 0.5477(2) -0.01772(18) 1.26754(18) 0.0187(4) Uani 1 1 d . . . . .
H14A H 0.5262 -0.0756 1.2258 0.028 Uiso 1 1 calc GR . . . .
H14B H 0.5039 -0.0608 1.3640 0.028 Uiso 1 1 calc GR . . . .
H14C H 0.6672 -0.0038 1.2411 0.028 Uiso 1 1 calc GR . . . .


_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 C7 2.0708(16) . ?
I1 C1 2.1182(16) . ?
Cl1 C4 1.7447(17) . ?
S1A C1A 1.6312(18) . ?
O1 C8 1.3534(19) . ?
O1 C13 1.4376(19) . ?
O3 C12 1.3570(19) . ?
O3 C15 1.4390(19) . ?
O2 C10 1.362(2) . ?
O2 C14 1.431(2) . ?
N1A C1A 1.170(2) . ?
C7 C12 1.396(2) . ?
C7 C8 1.408(2) . ?
C12 C11 1.392(2) . ?
C1 C6 1.387(2) . ?
C1 C2 1.384(2) . ?
C8 C9 1.377(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.390(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.397(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.383(2) . ?
C10 C9 1.396(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(2) . ?
C4 C3 1.386(2) . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C7 I1 C1 94.52(6) . . ?
C8 O1 C13 117.21(13) . . ?
C12 O3 C15 117.73(13) . . ?
C10 O2 C14 117.64(13) . . ?
C12 C7 I1 120.34(12) . . ?
C12 C7 C8 121.22(15) . . ?
C8 C7 I1 118.42(12) . . ?
O3 C12 C7 116.06(14) . . ?
O3 C12 C11 124.16(15) . . ?
C11 C12 C7 119.78(15) . . ?
C6 C1 I1 119.02(12) . . ?
C2 C1 I1 118.35(12) . . ?
C2 C1 C6 122.52(16) . . ?
O1 C8 C7 115.49(14) . . ?
O1 C8 C9 125.30(15) . . ?
C9 C8 C7 119.21(15) . . ?
C1 C6 H6 120.7 . . ?
C1 C6 C5 118.57(15) . . ?
C5 C6 H6 120.7 . . ?
C12 C11 H11 120.9 . . ?
C12 C11 C10 118.10(15) . . ?
C10 C11 H11 120.9 . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.12(16) . . ?
C4 C5 H5 120.4 . . ?
N1A C1A S1A 179.71(17) . . ?
O2 C10 C11 123.12(15) . . ?
O2 C10 C9 114.35(14) . . ?
C9 C10 C11 122.52(15) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.63(16) . . ?
C3 C2 H2 120.7 . . ?
C5 C4 Cl1 118.50(14) . . ?
C5 C4 C3 122.10(16) . . ?
C3 C4 Cl1 119.40(13) . . ?
C8 C9 C10 119.12(15) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.06(16) . . ?
C4 C3 H3 120.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2000278'
loop_
_audit_author_name
_audit_author_address
'Daniil Ivanov'
;SPbSU
Russia
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT431_5                   
;
PROBLEM: Short Inter HL..A Contact  I1       ..S1A      .       3.16 Ang.  
RESPONSE: The contacts are due to the C-I...X halogen bonding.
;
# end Validation Reply Form

_audit_creation_date             2019-09-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 F I O3, C N S'
_chemical_formula_sum            'C16 H15 F I N O3 S'
_chemical_formula_weight         447.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N1 I1 F1 C16 O3 H15'
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.8222(4)
_cell_length_b                   23.0680(10)
_cell_length_c                   8.0455(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.998(5)
_cell_angle_gamma                90
_cell_volume                     1723.64(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5919
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.6620
_cell_measurement_theta_min      3.3780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9191
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.816
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -92.00  -11.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4311  -57.0000    0.0000 81

#__ type_ start__ end____ width___ exp.time_
  2 omega  -85.00  -48.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4311 -178.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3686   19.0000  -30.0000 117

#__ type_ start__ end____ width___ exp.time_
  4 omega  -79.00  -40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4311 -178.0000 -180.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0235386000
_diffrn_orient_matrix_UB_12      -0.0041377000
_diffrn_orient_matrix_UB_13      0.0923341000
_diffrn_orient_matrix_UB_21      0.0589549000
_diffrn_orient_matrix_UB_22      0.0188854000
_diffrn_orient_matrix_UB_23      0.0088263000
_diffrn_orient_matrix_UB_31      -0.0423790000
_diffrn_orient_matrix_UB_32      0.0239921000
_diffrn_orient_matrix_UB_33      0.0089690000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3620
_reflns_number_total             3968
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3968
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0227
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0145P)²+0.5910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0476
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C6(H6), C3(H3), C9(H9), C5(H5)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.45157(2) 0.40923(2) 0.21806(2) 0.01109(5) Uani 1 1 d . . . . .
S1A S 0.78217(6) 0.59366(2) 0.16040(8) 0.02018(12) Uani 1 1 d . . . . .
O3 O 0.45128(15) 0.27452(7) 0.2323(2) 0.0161(3) Uani 1 1 d . . . . .
F1 F 0.84977(16) 0.39634(7) 0.99052(19) 0.0335(4) Uani 1 1 d . . . . .
O1 O 0.18085(15) 0.43246(6) 0.3136(2) 0.0163(3) Uani 1 1 d . . . . .
O2 O 0.02456(15) 0.23533(7) 0.3660(2) 0.0179(3) Uani 1 1 d . . . . .
N1A N 0.67161(19) 0.48437(9) 0.2068(2) 0.0191(4) Uani 1 1 d . . . . .
C1 C 0.5901(2) 0.40784(9) 0.4812(3) 0.0123(4) Uani 1 1 d . . . . .
C7 C 0.3078(2) 0.35144(9) 0.2695(3) 0.0117(4) Uani 1 1 d . . . . .
C12 C 0.3303(2) 0.29152(9) 0.2667(3) 0.0120(4) Uani 1 1 d . . . . .
C2 C 0.5387(2) 0.42722(9) 0.6130(3) 0.0153(4) Uani 1 1 d . . . . .
H2 H 0.4461 0.4422 0.5854 0.018 Uiso 1 1 calc R . . . .
C11 C 0.2332(2) 0.25359(9) 0.3006(3) 0.0141(4) Uani 1 1 d . . . . .
H11 H 0.2470 0.2137 0.2992 0.017 Uiso 1 1 calc R . . . .
C1A C 0.7175(2) 0.52951(10) 0.1889(3) 0.0134(4) Uani 1 1 d . . . . .
C8 C 0.1895(2) 0.37379(9) 0.3088(3) 0.0129(4) Uani 1 1 d . . . . .
C6 C 0.7288(2) 0.38645(10) 0.5177(3) 0.0168(4) Uani 1 1 d . . . . .
H6 H 0.7615 0.3745 0.4269 0.020 Uiso 1 1 calc R . . . .
C3 C 0.6277(2) 0.42392(10) 0.7866(3) 0.0184(5) Uani 1 1 d . . . . .
H3 H 0.5961 0.4366 0.8775 0.022 Uiso 1 1 calc R . . . .
C9 C 0.0916(2) 0.33596(9) 0.3431(3) 0.0147(4) Uani 1 1 d . . . . .
H9 H 0.0125 0.3501 0.3697 0.018 Uiso 1 1 calc R . . . .
C15 C 0.4783(2) 0.21309(10) 0.2354(3) 0.0198(5) Uani 1 1 d . . . . .
H15A H 0.3971 0.1940 0.1536 0.030 Uiso 1 1 calc GR . . . .
H15B H 0.4930 0.1984 0.3516 0.030 Uiso 1 1 calc GR . . . .
H15C H 0.5626 0.2060 0.2031 0.030 Uiso 1 1 calc GR . . . .
C13 C 0.0608(2) 0.45766(10) 0.3527(3) 0.0179(5) Uani 1 1 d . . . . .
H13A H -0.0273 0.4460 0.2651 0.027 Uiso 1 1 calc GR . . . .
H13B H 0.0685 0.4991 0.3529 0.027 Uiso 1 1 calc GR . . . .
H13C H 0.0611 0.4447 0.4662 0.027 Uiso 1 1 calc GR . . . .
C10 C 0.1144(2) 0.27631(9) 0.3369(3) 0.0135(4) Uani 1 1 d . . . . .
C4 C 0.7635(2) 0.40153(10) 0.8208(3) 0.0205(5) Uani 1 1 d . . . . .
C5 C 0.8180(2) 0.38316(10) 0.6906(3) 0.0196(5) Uani 1 1 d . . . . .
H5 H 0.9115 0.3691 0.7187 0.024 Uiso 1 1 calc R . . . .
C14 C -0.0974(2) 0.25489(11) 0.4100(3) 0.0226(5) Uani 1 1 d . . . . .
H14A H -0.1602 0.2765 0.3134 0.034 Uiso 1 1 calc GR . . . .
H14B H -0.0657 0.2792 0.5122 0.034 Uiso 1 1 calc GR . . . .
H14C H -0.1481 0.2221 0.4341 0.034 Uiso 1 1 calc GR . . . .


_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 2.112(2) . ?
I1 C7 2.079(2) . ?
S1A C1A 1.656(2) . ?
O3 C12 1.363(2) . ?
O3 C15 1.440(3) . ?
F1 C4 1.358(3) . ?
O1 C8 1.357(3) . ?
O1 C13 1.438(2) . ?
O2 C10 1.365(2) . ?
O2 C14 1.428(2) . ?
N1A C1A 1.162(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.388(3) . ?
C7 C12 1.401(3) . ?
C7 C8 1.399(3) . ?
C12 C11 1.385(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.393(3) . ?
C8 C9 1.391(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C7 I1 C1 92.77(8) . . ?
C12 O3 C15 116.57(16) . . ?
C8 O1 C13 118.19(16) . . ?
C10 O2 C14 117.74(17) . . ?
C2 C1 I1 119.00(15) . . ?
C6 C1 I1 119.03(16) . . ?
C6 C1 C2 122.0(2) . . ?
C12 C7 I1 120.58(14) . . ?
C8 C7 I1 118.49(15) . . ?
C8 C7 C12 120.92(18) . . ?
O3 C12 C7 116.07(18) . . ?
O3 C12 C11 124.06(19) . . ?
C11 C12 C7 119.86(18) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C12 C11 H11 120.6 . . ?
C12 C11 C10 118.71(19) . . ?
C10 C11 H11 120.6 . . ?
N1A C1A S1A 179.2(2) . . ?
O1 C8 C7 115.98(18) . . ?
O1 C8 C9 124.50(18) . . ?
C9 C8 C7 119.50(19) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.4(2) . . ?
C4 C3 H3 120.8 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.78(18) . . ?
C10 C9 H9 120.6 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C10 C11 114.05(18) . . ?
O2 C10 C9 123.74(18) . . ?
C11 C10 C9 122.20(19) . . ?
F1 C4 C3 118.8(2) . . ?
F1 C4 C5 117.7(2) . . ?
C3 C4 C5 123.5(2) . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 2000282'
loop_
_audit_author_name
_audit_author_address
'Daniil Ivanov'
;SPbSU
Russia
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT431_9                   
;
PROBLEM: Short Inter HL..A Contact  I1       ..N1A      .       2.85 Ang.
RESPONSE: The contacts are due to the C-I...X halogen bonding.
;
# end Validation Reply Form

_audit_creation_date             2020-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 Br I O3, C N S'
_chemical_formula_sum            'C16 H15 Br I N O3 S'
_chemical_formula_weight         508.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H15 Br1 I1 N1 O3 S1'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3448(5)
_cell_length_b                   10.7012(8)
_cell_length_c                   11.2708(9)
_cell_angle_alpha                67.245(7)
_cell_angle_beta                 70.464(6)
_cell_angle_gamma                83.175(5)
_cell_volume                     874.64(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5390
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2900
_cell_measurement_theta_min      4.4650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    18.294
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8682
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.433
_diffrn_reflns_theta_min         4.481
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00 -48.00   0.50    1.00    --  -38.95 138.00 -22.00   68
  2  ω    -86.00 -14.00   0.50    1.00    --  -38.95 131.00 162.00  144
  3  ω     12.00  49.00   0.50    1.00    --   38.95-131.00  91.00   74
  4  ω     66.00  91.00   0.50    1.00    --   38.95-131.00  91.00   50
  5  ω     76.00 109.00   0.50    2.50    --  100.00-131.00  91.00   66
  6  ω     89.00 114.00   0.50    2.50    --  100.00 138.00 -22.00   50
  7  ω    108.00 148.00   0.50    2.50    --  100.00 131.00 162.00   80
  8  ω     38.00  67.00   0.50    2.50    --  100.00-138.00 -83.00   58
  9  ω    -38.00  27.00   0.50    1.00    --  -38.95  32.00 -90.00  130
 10  ω    -80.00 -31.00   0.50    1.00    --  -38.95 -43.00 -60.00   98
 11  ω   -106.00 -81.00   0.50    1.00    --  -38.95 -32.00  30.00   50
 12  ω    -57.00 -25.00   0.50    1.00    --  -38.95 -32.00  30.00   64
 13  ω     32.00 105.00   0.50    1.00    --   38.95  43.00 -60.00  146
 14  ω    -22.00   3.00   0.50    1.00    --   38.95 -77.00 -90.00   50
 15  ω     33.00  58.00   0.50    1.00    --   38.95-138.00 -83.00   50
 16  ω     35.00  61.00   0.50    1.00    --   38.95 -65.00 -60.00   52
 17  ω      6.00  47.00   0.50    1.00    --   38.95 -43.00 120.00   82
 18  ω    -26.00  26.00   0.50    1.00    --   38.95 -32.00  90.00  104
 19  ω    -24.00  61.00   0.50    1.00    --   38.95 -65.00  60.00  170
 20  ω     18.00  64.00   0.50    1.00    --   38.95 -77.00 -90.00   92
 21  ω    -25.00   0.00   0.50    1.00    --   38.95 -43.00 120.00   50
 22  ω     82.00 107.00   0.50    1.00    --   38.95  11.00-120.00   50
 23  ω      4.00  30.00   0.50    1.00    --   38.95 -65.00 -60.00   52
 24  ω     40.00 102.00   0.50    1.00    --   38.95  32.00  30.00  124
 25  ω     10.00  38.00   0.50    1.00    --   38.95  11.00-120.00   56
 26  ω     42.00  67.00   0.50    1.00    --   38.95-138.00-150.00   50
 27  ω     88.00 157.00   0.50    2.50    --  100.00 111.00 150.00  138
 28  ω     42.00  79.00   0.50    2.50    --  100.00-111.00  90.00   74
 29  ω     92.00 157.00   0.50    2.50    --  100.00  93.00-150.00  130
 30  ω     42.00  67.00   0.50    2.50    --  100.00 -93.00  90.00   50
 31  ω    116.00 152.00   0.50    2.50    --  100.00  37.00  90.00   72
 32  ω    108.00 156.00   0.50    2.50    --  100.00  15.00  30.00   96
 33  ω     30.00  71.00   0.50    2.50    --  100.00 -86.00 150.00   82
 34  ω     83.00 122.00   0.50    2.50    --  100.00 -86.00 150.00   78
 35  ω     63.00  88.00   0.50    2.50    --  100.00 -69.00  30.00   50
 36  ω     82.00 113.00   0.50    2.50    --  100.00 -30.00-120.00   62
 37  ω    124.00 151.00   0.50    2.50    --  100.00  45.00 -30.00   54
 38  ω     31.00  97.00   0.50    2.50    --  100.00 -30.00   0.00  132
 39  ω     43.00 120.00   0.50    2.50    --  100.00 -61.00-120.00  154
 40  ω     51.00 115.00   0.50    2.50    --  100.00-133.00  60.00  128
 41  ω     86.00 157.00   0.50    2.50    --  100.00  37.00 -60.00  142
 42  ω     33.00  76.00   0.50    2.50    --  100.00 -30.00-120.00   86
 43  ω     70.00 119.00   0.50    2.50    --  100.00 -53.00 150.00   98
 44  ω    104.00 129.00   0.50    2.50    --  100.00 -15.00  90.00   50
 45  ω     37.00  62.00   0.50    2.50    --  100.00 -53.00 150.00   50
 46  ω     82.00 113.00   0.50    2.50    --  100.00  45.00 -30.00   62
 47  ω     43.00  86.00   0.50    2.50    --  100.00 -15.00  90.00   86
 48  ω    102.00 129.00   0.50    2.50    --  100.00 178.00  90.00   54
 49  ω     69.00 123.00   0.50    2.50    --  100.00 -77.00  90.00  108
 50  ω     37.00  91.00   0.50    2.50    --  100.00-133.00-180.00  108
 51  ω    115.00 141.00   0.50    2.50    --  100.00 111.00-150.00   52
 52  ω     84.00 111.00   0.50    2.50    --  100.00  93.00 -60.00   54
 53  ω     64.00  90.00   0.50    2.50    --  100.00 -93.00-120.00   52
 54  ω     81.00 157.00   0.50    2.50    --  100.00  53.00-180.00  152
 55  ω     31.00  78.00   0.50    2.50    --  100.00 -22.00  60.00   94
 56  ω     33.00 102.00   0.50    2.50    --  100.00-111.00-120.00  138
 57  ω     79.00 129.00   0.50    2.50    --  100.00  69.00-120.00  100
 58  ω     61.00  88.00   0.50    2.50    --  100.00 -93.00 -90.00   54
 59  ω     77.00 106.00   0.50    2.50    --  100.00-111.00 -30.00   58
 60  ω     49.00 108.00   0.50    2.50    --  100.00-111.00 120.00  118
 61  ω     65.00 105.00   0.50    2.50    --  100.00 -93.00  30.00   80
 62  ω     93.00 118.00   0.50    2.50    --  100.00-133.00 -90.00   50
 63  ω     62.00 119.00   0.50    2.50    --  100.00 -61.00  60.00  114
 64  ω    109.00 134.00   0.50    2.50    --  100.00  37.00 -90.00   50
 65  ω     36.00  61.00   0.50    1.00    --   38.95  65.00-180.00   50
 66  ω    -50.00 -25.00   0.50    1.00    --    4.00 132.00-145.15   50
 67  ω    -14.00  11.00   0.50    1.00    --   24.00 104.00  59.61   50
 68  ω    -13.00  12.00   0.50    1.00    --   24.00 102.00-141.10   50
 69  ω     -4.00  21.00   0.50    1.00    --   28.00  90.00  38.09   50
 70  ω      0.00  13.00   0.50    1.00    --   32.00  90.00-150.32   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1847758000
_diffrn_orient_matrix_UB_12      0.0340800000
_diffrn_orient_matrix_UB_13      -0.0938088000
_diffrn_orient_matrix_UB_21      0.0622969000
_diffrn_orient_matrix_UB_22      -0.0516754000
_diffrn_orient_matrix_UB_23      0.1247913000
_diffrn_orient_matrix_UB_31      0.0188955000
_diffrn_orient_matrix_UB_32      -0.1433277000
_diffrn_orient_matrix_UB_33      -0.0042036000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3046
_reflns_number_total             3323
_reflns_odcompleteness_completeness 98.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.967
_refine_diff_density_min         -1.175
_refine_diff_density_rms         0.159
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0968
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C3(H3), C9(H9), C2(H2), C6(H6)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.61648(3) 0.47591(2) 0.62302(3) 0.01609(11) Uani 1 1 d . . . . .
Br1 Br 1.20548(6) 0.83803(5) 0.64716(6) 0.02613(14) Uani 1 1 d . . . . .
S1A S 0.89650(15) 0.77434(11) 0.08486(12) 0.0239(3) Uani 1 1 d . . . . .
O1 O 0.3634(4) 0.4988(3) 0.8801(3) 0.0193(7) Uani 1 1 d . . . . .
O2 O 0.4724(4) 0.1035(3) 1.2248(3) 0.0223(7) Uani 1 1 d . . . . .
O3 O 0.7814(4) 0.2044(3) 0.7492(3) 0.0202(7) Uani 1 1 d . . . . .
N1A N 0.6791(5) 0.6682(4) 0.3525(4) 0.0229(8) Uani 1 1 d . . . . .
C7 C 0.5725(5) 0.3475(4) 0.8232(5) 0.0170(9) Uani 1 1 d . . . . .
C12 C 0.6650(5) 0.2276(4) 0.8550(5) 0.0164(8) Uani 1 1 d . . . . .
C5 C 1.0626(6) 0.5989(4) 0.6689(5) 0.0207(9) Uani 1 1 d . . . . .
H5 H 1.1548 0.5563 0.6966 0.025 Uiso 1 1 calc R . . . .
C8 C 0.4469(6) 0.3815(4) 0.9238(5) 0.0172(9) Uani 1 1 d . . . . .
C4 C 1.0418(6) 0.7381(4) 0.6345(5) 0.0193(9) Uani 1 1 d . . . . .
C13 C 0.2235(6) 0.5303(5) 0.9803(5) 0.0204(9) Uani 1 1 d . . . . .
H13A H 0.1683 0.6104 0.9365 0.031 Uiso 1 1 calc GR . . . .
H13B H 0.2652 0.5455 1.0434 0.031 Uiso 1 1 calc GR . . . .
H13C H 0.1436 0.4559 1.0278 0.031 Uiso 1 1 calc GR . . . .
C11 C 0.6334(6) 0.1410(4) 0.9916(5) 0.0183(9) Uani 1 1 d . . . . .
H11 H 0.6929 0.0608 1.0154 0.022 Uiso 1 1 calc R . . . .
C10 C 0.5114(6) 0.1787(4) 1.0891(5) 0.0170(9) Uani 1 1 d . . . . .
C15 C 0.8679(6) 0.0752(4) 0.7783(5) 0.0219(10) Uani 1 1 d . . . . .
H15A H 0.9445 0.0695 0.6953 0.033 Uiso 1 1 calc GR . . . .
H15B H 0.7855 0.0028 0.8207 0.033 Uiso 1 1 calc GR . . . .
H15C H 0.9308 0.0678 0.8381 0.033 Uiso 1 1 calc GR . . . .
C3 C 0.9052(6) 0.8041(4) 0.5951(5) 0.0221(10) Uani 1 1 d . . . . .
H3 H 0.8938 0.8972 0.5734 0.027 Uiso 1 1 calc R . . . .
C9 C 0.4166(6) 0.2975(4) 1.0583(5) 0.0183(9) Uani 1 1 d . . . . .
H9 H 0.3350 0.3194 1.1269 0.022 Uiso 1 1 calc R . . . .
C2 C 0.7839(6) 0.7297(4) 0.5883(5) 0.0204(9) Uani 1 1 d . . . . .
H2 H 0.6903 0.7717 0.5624 0.024 Uiso 1 1 calc R . . . .
C1 C 0.8076(6) 0.5911(4) 0.6213(5) 0.0188(9) Uani 1 1 d . . . . .
C14 C 0.5508(6) -0.0274(5) 1.2644(5) 0.0236(10) Uani 1 1 d . . . . .
H14A H 0.5350 -0.0773 1.2143 0.035 Uiso 1 1 calc GR . . . .
H14B H 0.4994 -0.0764 1.3596 0.035 Uiso 1 1 calc GR . . . .
H14C H 0.6702 -0.0155 1.2455 0.035 Uiso 1 1 calc GR . . . .
C6 C 0.9439(6) 0.5251(4) 0.6613(5) 0.0198(9) Uani 1 1 d . . . . .
H6 H 0.9558 0.4321 0.6828 0.024 Uiso 1 1 calc R . . . .
C1A C 0.7691(6) 0.7128(4) 0.2413(5) 0.0196(10) 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 C7 2.069(5) . ?
I1 C1 2.119(5) . ?
Br1 C4 1.905(5) . ?
S1A C1A 1.639(5) . ?
O1 C8 1.359(5) . ?
O1 C13 1.439(5) . ?
O2 C10 1.367(5) . ?
O2 C14 1.443(5) . ?
O3 C12 1.350(6) . ?
O3 C15 1.453(5) . ?
N1A C1A 1.165(7) . ?
C7 C12 1.401(6) . ?
C7 C8 1.397(6) . ?
C12 C11 1.408(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.391(6) . ?
C5 C6 1.381(7) . ?
C8 C9 1.383(7) . ?
C4 C3 1.378(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C10 1.380(7) . ?
C10 C9 1.403(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C2 1.399(7) . ?
C9 H9 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.389(6) . ?
C1 C6 1.379(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C6 H6 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
C7 I1 C1 94.52(17) . . ?
C8 O1 C13 117.1(3) . . ?
C10 O2 C14 117.3(4) . . ?
C12 O3 C15 117.2(4) . . ?
C12 C7 I1 119.9(3) . . ?
C8 C7 I1 118.6(3) . . ?
C8 C7 C12 121.5(4) . . ?
O3 C12 C7 116.2(4) . . ?
O3 C12 C11 124.5(4) . . ?
C7 C12 C11 119.3(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C6 C5 C4 118.8(4) . . ?
O1 C8 C7 116.0(4) . . ?
O1 C8 C9 124.5(4) . . ?
C9 C8 C7 119.5(4) . . ?
C5 C4 Br1 118.3(4) . . ?
C3 C4 Br1 119.6(3) . . ?
C3 C4 C5 122.1(4) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C11 H11 121.0 . . ?
C10 C11 C12 118.0(4) . . ?
C10 C11 H11 121.0 . . ?
O2 C10 C11 122.9(4) . . ?
O2 C10 C9 113.9(4) . . ?
C11 C10 C9 123.2(4) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C3 H3 120.4 . . ?
C4 C3 C2 119.3(4) . . ?
C2 C3 H3 120.4 . . ?
C8 C9 C10 118.6(4) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C3 C2 H2 121.0 . . ?
C1 C2 C3 118.0(4) . . ?
C1 C2 H2 121.0 . . ?
C2 C1 I1 118.1(3) . . ?
C6 C1 I1 119.1(3) . . ?
C6 C1 C2 122.6(4) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 C5 119.2(4) . . ?
C1 C6 H6 120.4 . . ?
N1A C1A S1A 179.5(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.192
_oxdiff_exptl_absorpt_empirical_full_min 0.688
