# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_18384_imv670
_database_code_depnum_ccdc_archive 'CCDC 2212224'
loop_
_audit_author_name
_audit_author_address
'Irina Aliyarova'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2022-11-22 downloaded from the CCDC.
;
_audit_creation_date             2022-08-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 I N3, C F3 O3 S'
_chemical_formula_sum            'C15 H9 F3 I N3 O3 S'
_chemical_formula_weight         495.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H9 F3 I N3 O3 S'
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'
F F 0.0727 0.0534 '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      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                   12.4433(2)
_cell_length_b                   12.38770(10)
_cell_length_c                   11.9729(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.297(2)
_cell_angle_gamma                90
_cell_volume                     1654.55(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10370
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.0150
_cell_measurement_theta_min      3.5150
_shelx_estimated_absorpt_T_max   0.430
_shelx_estimated_absorpt_T_min   0.201
_exptl_absorpt_coefficient_mu    16.911
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15508
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.133
_diffrn_reflns_theta_min         3.963
_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 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -33.00   0.50    0.20    --  -39.58 -62.00 168.00  106
  2  ω     14.00  47.00   0.50    0.20    --   39.58 -62.00 168.00   66
  3  ω     21.00  52.00   0.50    0.20    --   39.58  62.00 -53.00   62
  4  ω     58.00  88.00   0.50    0.20    --   39.58  62.00 -53.00   60
  5  ω     35.00 116.00   0.50    0.40    --   94.79 -62.00 168.00  162
  6  ω     74.00 157.00   0.50    0.40    --   94.79  62.00 -53.00  166
  7  ω    -52.00 -26.00   0.50    0.20    --  -39.58 -54.00  60.00   52
  8  ω   -109.00 -83.00   0.50    0.20    --  -39.58 -21.00  30.00   52
  9  ω    -75.00 -18.00   0.50    0.20    --  -39.58 104.00 -60.00  114
 10  ω    -12.00  14.00   0.50    0.20    --  -39.58 104.00 -60.00   52
 11  ω    -94.00 -61.00   0.50    0.20    --  -39.58 -54.00  60.00   66
 12  ω    -56.00 -28.00   0.50    0.20    --  -39.58 -21.00  30.00   56
 13  ω    -34.00  15.00   0.50    0.20    --  -39.58  62.00 -53.00   98
 14  ω   -110.00 -47.00   0.50    0.20    --  -39.58 -21.00 -30.00  126
 15  ω    -97.00 -17.00   0.50    0.20    --  -39.58 138.00  60.00  160
 16  ω     29.00  74.00   0.50    0.20    --   39.58  43.00  90.00   90
 17  ω     33.00  73.00   0.50    0.20    --   39.58  43.00-120.00   80
 18  ω     89.00 119.00   0.50    0.40    --   94.79  77.00  60.00   60
 19  ω    121.00 156.00   0.50    0.40    --   94.79  33.00  30.00   70
 20  ω     32.00 117.00   0.50    0.40    --   94.79 -68.00 -30.00  170
 21  ω     83.00 157.00   0.50    0.40    --   94.79  33.00   0.00  148
 22  ω     84.00 118.00   0.50    0.40    --   94.79  33.00  30.00   68
 23  ω     86.00 111.00   0.50    0.40    --   94.79 -59.00 -60.00   50
 24  ω     29.00 124.00   0.50    0.40    --   94.79 -87.00-180.00  190
 25  ω     31.00  59.00   0.50    0.40    --   94.79 -59.00 -60.00   56
 26  ω    124.00 156.00   0.50    0.40    --   94.79  17.00 -90.00   64
 27  ω     29.00  54.00   0.50    0.40    --   94.79 -17.00 120.00   50
 28  ω     66.00 110.00   0.50    0.40    --   94.79 -17.00 120.00   88
 29  ω    128.00 153.00   0.50    0.40    --   94.79  77.00  60.00   50
 30  ω    117.00 143.00   0.50    0.40    --   94.79  96.00  30.00   52
 31  ω     80.00 157.00   0.50    0.40    --   94.79  42.00  60.00  154
 32  ω    113.00 151.00   0.50    0.40    --   94.79 117.00-120.00   76
 33  ω     76.00 102.00   0.50    0.20    --   39.58  62.00 -53.00   52
 34  ω    -46.00 -19.00   0.50    0.20    --  -39.58  32.00 150.00   54
 35  ω     -9.00  28.00   0.50    0.20    --  -39.58  32.00 150.00   74
 36  ω     33.00  78.00   0.50    0.20    --   39.58  43.00 120.00   90
 37  ω     12.00  39.00   0.50    0.20    --   39.58 -32.00   0.00   54
 38  ω     -5.00  27.00   0.50    0.20    --   39.58 -21.00-180.00   64
 39  ω     75.00 101.00   0.50    0.40    --   94.79  59.00  30.00   52
 40  ω     72.00  98.00   0.50    0.40    --   94.79  68.00  60.00   52
 41  ω     60.00 111.00   0.50    0.40    --   94.79 -17.00 -60.00  102
 42  ω     72.00  97.00   0.50    0.40    --   94.79  68.00  30.00   50
 43  ω     77.00 129.00   0.50    0.40    --   94.79  17.00 -60.00  104
 44  ω     72.00  97.00   0.50    0.40    --   94.79  68.00   0.00   50
 45  ω     33.00  83.00   0.50    0.40    --   94.79 -77.00 -90.00  100
 46  ω     51.00  98.00   0.50    0.40    --   94.79 -33.00 -60.00   94
 47  ω     77.00 103.00   0.50    0.40    --   94.79  50.00  90.00   52
 48  ω     78.00 104.00   0.50    0.40    --   94.79  50.00  60.00   52
 49  ω    132.00 157.00   0.50    0.40    --   94.79  33.00-120.00   50
 50  ω    112.00 138.00   0.50    0.40    --   94.79  50.00  90.00   52
 51  ω     52.00  79.00   0.50    0.40    --   94.79 -25.00   0.00   54
 52  ω     88.00 125.00   0.50    0.40    --   94.79  33.00-120.00   74
 53  ω     49.00 110.00   0.50    0.40    --   94.79 -42.00 150.00  122
 54  ω     92.00 143.00   0.50    0.40    --   94.79  68.00  90.00  102
 55  ω    123.00 148.00   0.50    0.40    --   94.79  96.00 -30.00   50
 56  ω     76.00 102.00   0.50    0.40    --   94.79  59.00  60.00   52
 57  ω     75.00 102.00   0.50    0.40    --   94.79  59.00  90.00   54
 58  ω     87.00 153.00   0.50    0.40    --   94.79  96.00 -90.00  132
 59  ω     90.00 116.00   0.50    0.40    --   94.79  77.00-180.00   52
 60  ω     76.00 102.00   0.50    0.40    --   94.79  50.00  30.00   52
 61  ω     75.00 100.00   0.50    0.40    --   94.79  57.00  75.11   50
 62  ω     35.00 125.00   0.50    0.40    --   94.79-145.00-150.00  180
;
_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      -0.1216381000
_diffrn_orient_matrix_UB_12      -0.0480245000
_diffrn_orient_matrix_UB_13      -0.0208348000
_diffrn_orient_matrix_UB_21      0.0030837000
_diffrn_orient_matrix_UB_22      -0.0759839000
_diffrn_orient_matrix_UB_23      -0.1003962000
_diffrn_orient_matrix_UB_31      0.0653130000
_diffrn_orient_matrix_UB_32      -0.0859459000
_diffrn_orient_matrix_UB_33      0.1004438000
_diffrn_oxdiff_digest_frames     
;
01196d23316686d7593c784d6195ee2844000381cd5
;
_diffrn_oxdiff_digest_hkl        
;
012031a42c1c539f94f6259fdf453afcc22dfc
;
_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                2908
_reflns_number_total             3012
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.00017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0209
_refine_ls_restrained_S_all      1.030
_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)+(0.0287P)²+1.1036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0520
_refine_ls_wR_factor_ref         0.0525
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14)
;
_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 0.58754(2) 0.15327(2) 0.41897(2) 0.01424(7) Uani 1 1 d . . . . .
N1 N 0.7995(2) 0.17432(17) 0.2386(2) 0.0173(4) Uani 1 1 d . . . . .
N2 N 0.8014(2) 0.06400(17) 0.2373(2) 0.0205(5) Uani 1 1 d . . . . .
N3 N 0.9065(2) 0.32675(18) 0.2299(2) 0.0211(5) Uani 1 1 d . . . . .
C1 C 0.7352(2) 0.0310(2) 0.2918(2) 0.0205(5) Uani 1 1 d . . . . .
H1 H 0.720408 -0.042204 0.304323 0.025 Uiso 1 1 calc R . . . .
C2 C 0.6903(2) 0.1211(2) 0.3280(2) 0.0171(5) Uani 1 1 d . . . . .
C3 C 0.7305(2) 0.2128(2) 0.2933(2) 0.0154(5) Uani 1 1 d . . . . .
C4 C 0.6918(2) 0.3185(2) 0.3171(2) 0.0158(5) Uani 1 1 d . . . . .
C5 C 0.6197(2) 0.31263(19) 0.3801(2) 0.0157(5) Uani 1 1 d . . . . .
C6 C 0.5745(2) 0.4007(2) 0.4155(2) 0.0190(5) Uani 1 1 d . . . . .
H6 H 0.526066 0.392228 0.457831 0.023 Uiso 1 1 calc R . . . .
C7 C 0.6028(2) 0.5028(2) 0.3868(3) 0.0219(5) Uani 1 1 d . . . . .
H7 H 0.573729 0.565681 0.409932 0.026 Uiso 1 1 calc R . . . .
C8 C 0.6733(2) 0.5123(2) 0.3244(2) 0.0206(5) Uani 1 1 d . . . . .
H8 H 0.692547 0.582170 0.305983 0.025 Uiso 1 1 calc R . . . .
C9 C 0.7166(2) 0.4223(2) 0.2881(2) 0.0181(5) Uani 1 1 d . . . . .
H9 H 0.763080 0.431168 0.243617 0.022 Uiso 1 1 calc R . . . .
C10 C 0.8712(2) 0.2281(2) 0.1888(2) 0.0182(5) Uani 1 1 d . . . . .
C11 C 0.9721(2) 0.3790(2) 0.1828(3) 0.0261(6) Uani 1 1 d . . . . .
H11 H 0.997078 0.450764 0.209715 0.031 Uiso 1 1 calc R . . . .
C12 C 1.0045(3) 0.3337(2) 0.0980(3) 0.0277(6) Uani 1 1 d . . . . .
H12 H 1.050796 0.373346 0.066862 0.033 Uiso 1 1 calc R . . . .
C13 C 0.9686(3) 0.2288(2) 0.0581(3) 0.0275(6) Uani 1 1 d . . . . .
H13 H 0.991078 0.195248 0.000257 0.033 Uiso 1 1 calc R . . . .
C14 C 0.8996(2) 0.1735(2) 0.1038(2) 0.0218(5) Uani 1 1 d . . . . .
H14 H 0.873046 0.101779 0.078379 0.026 Uiso 1 1 calc R . . . .
S1 S 0.37446(5) 0.18136(5) 0.55234(5) 0.01554(13) Uani 1 1 d . . . . .
F1 F 0.14396(16) 0.15686(15) 0.41452(18) 0.0401(5) Uani 1 1 d . . . . .
F2 F 0.20588(17) 0.31987(15) 0.42614(17) 0.0400(4) Uani 1 1 d . . . . .
F3 F 0.24076(17) 0.20414(17) 0.31281(15) 0.0394(4) Uani 1 1 d . . . . .
O1 O 0.35355(17) 0.20928(15) 0.65756(16) 0.0223(4) Uani 1 1 d . . . . .
O2 O 0.46252(16) 0.24810(14) 0.53627(18) 0.0215(4) Uani 1 1 d . . . . .
O3 O 0.38701(18) 0.06765(14) 0.53387(19) 0.0251(4) Uani 1 1 d . . . . .
C15 C 0.2341(2) 0.2174(2) 0.4191(2) 0.0227(5) 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 C2 2.053(2) . ?
I1 C5 2.107(2) . ?
N1 N2 1.367(3) . ?
N1 C3 1.376(3) . ?
N1 C10 1.437(3) . ?
N2 C1 1.322(3) . ?
N3 C10 1.318(3) . ?
N3 C11 1.346(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.400(4) . ?
C2 C3 1.378(4) . ?
C3 C4 1.466(3) . ?
C4 C5 1.406(4) . ?
C4 C9 1.402(3) . ?
C5 C6 1.377(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C14 1.391(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.368(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(4) . ?
C14 H14 0.9500 . ?
S1 O1 1.4369(18) . ?
S1 O2 1.4519(18) . ?
S1 O3 1.4451(18) . ?
S1 C15 1.824(3) . ?
F1 C15 1.330(3) . ?
F2 C15 1.330(3) . ?
F3 C15 1.322(3) . ?

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
C2 I1 C5 80.85(10) . . ?
N2 N1 C3 111.7(2) . . ?
N2 N1 C10 116.2(2) . . ?
C3 N1 C10 132.1(2) . . ?
C1 N2 N1 106.6(2) . . ?
C10 N3 C11 116.9(2) . . ?
N2 C1 H1 125.4 . . ?
N2 C1 C2 109.1(2) . . ?
C2 C1 H1 125.4 . . ?
C1 C2 I1 138.35(19) . . ?
C3 C2 I1 113.23(18) . . ?
C3 C2 C1 108.4(2) . . ?
N1 C3 C2 104.2(2) . . ?
N1 C3 C4 136.9(2) . . ?
C2 C3 C4 118.9(2) . . ?
C5 C4 C3 113.6(2) . . ?
C9 C4 C3 130.1(2) . . ?
C9 C4 C5 116.3(2) . . ?
C4 C5 I1 113.29(18) . . ?
C6 C5 I1 122.04(18) . . ?
C6 C5 C4 124.7(2) . . ?
C5 C6 H6 121.3 . . ?
C5 C6 C7 117.4(2) . . ?
C7 C6 H6 121.3 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.1 . . ?
C7 C8 C9 121.8(2) . . ?
C9 C8 H8 119.1 . . ?
C4 C9 H9 120.0 . . ?
C8 C9 C4 120.0(2) . . ?
C8 C9 H9 120.0 . . ?
N3 C10 N1 116.1(2) . . ?
N3 C10 C14 125.0(2) . . ?
C14 C10 N1 118.9(2) . . ?
N3 C11 H11 118.4 . . ?
N3 C11 C12 123.1(3) . . ?
C12 C11 H11 118.4 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 118.9(3) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C10 C14 H14 121.6 . . ?
C13 C14 C10 116.8(3) . . ?
C13 C14 H14 121.6 . . ?
O1 S1 O2 114.81(11) . . ?
O1 S1 O3 116.27(11) . . ?
O1 S1 C15 103.46(11) . . ?
O2 S1 C15 103.38(12) . . ?
O3 S1 O2 113.31(11) . . ?
O3 S1 C15 103.36(12) . . ?
F1 C15 S1 111.20(19) . . ?
F1 C15 F2 107.4(2) . . ?
F2 C15 S1 110.82(18) . . ?
F3 C15 S1 111.57(18) . . ?
F3 C15 F1 107.6(2) . . ?
F3 C15 F2 108.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C2 C3 N1 178.09(16) . . . . ?
I1 C2 C3 C4 -3.4(3) . . . . ?
I1 C5 C6 C7 179.02(19) . . . . ?
N1 N2 C1 C2 0.1(3) . . . . ?
N1 C3 C4 C5 -179.4(3) . . . . ?
N1 C3 C4 C9 -0.1(5) . . . . ?
N1 C10 C14 C13 179.8(2) . . . . ?
N2 N1 C3 C2 0.8(3) . . . . ?
N2 N1 C3 C4 -177.2(3) . . . . ?
N2 N1 C10 N3 -155.4(2) . . . . ?
N2 N1 C10 C14 23.7(3) . . . . ?
N2 C1 C2 I1 -177.9(2) . . . . ?
N2 C1 C2 C3 0.4(3) . . . . ?
N3 C10 C14 C13 -1.2(4) . . . . ?
N3 C11 C12 C13 -0.1(4) . . . . ?
C1 C2 C3 N1 -0.7(3) . . . . ?
C1 C2 C3 C4 177.8(2) . . . . ?
C2 C3 C4 C5 2.8(3) . . . . ?
C2 C3 C4 C9 -178.0(3) . . . . ?
C3 N1 N2 C1 -0.6(3) . . . . ?
C3 N1 C10 N3 21.8(4) . . . . ?
C3 N1 C10 C14 -159.1(3) . . . . ?
C3 C4 C5 I1 -0.7(3) . . . . ?
C3 C4 C5 C6 178.5(2) . . . . ?
C3 C4 C9 C8 -177.5(3) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C4 C9 C8 1.7(4) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C6 C7 C8 C9 0.5(4) . . . . ?
C7 C8 C9 C4 -1.6(4) . . . . ?
C9 C4 C5 I1 179.92(17) . . . . ?
C9 C4 C5 C6 -0.9(4) . . . . ?
C10 N1 N2 C1 177.1(2) . . . . ?
C10 N1 C3 C2 -176.5(2) . . . . ?
C10 N1 C3 C4 5.5(5) . . . . ?
C10 N3 C11 C12 -1.3(4) . . . . ?
C11 N3 C10 N1 -179.0(2) . . . . ?
C11 N3 C10 C14 2.0(4) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C13 C14 C10 -0.3(4) . . . . ?
O1 S1 C15 F1 -64.6(2) . . . . ?
O1 S1 C15 F2 54.8(2) . . . . ?
O1 S1 C15 F3 175.32(19) . . . . ?
O2 S1 C15 F1 175.41(18) . . . . ?
O2 S1 C15 F2 -65.2(2) . . . . ?
O2 S1 C15 F3 55.3(2) . . . . ?
O3 S1 C15 F1 57.1(2) . . . . ?
O3 S1 C15 F2 176.48(18) . . . . ?
O3 S1 C15 F3 -63.0(2) . . . . ?

_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 1.512
_oxdiff_exptl_absorpt_empirical_full_min 0.748
####################################################################### 
# 
# 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_ver0-22071_pda-0401
_database_code_depnum_ccdc_archive 'CCDC 2212225'
loop_
_audit_author_name
_audit_author_address
'Irina Aliyarova'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2022-11-22 downloaded from the CCDC.
;
_audit_creation_date             2022-08-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 I N2, C F3 O3 S'
_chemical_formula_sum            'C16 H10 F3 I N2 O3 S'
_chemical_formula_weight         494.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 O4 Ag I N2'
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'
F F 0.0727 0.0534 '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      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                   5.68910(10)
_cell_length_b                   30.3093(6)
_cell_length_c                   9.9602(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.586(3)
_cell_angle_gamma                90
_cell_volume                     1654.31(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11448
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.7960
_cell_measurement_theta_min      2.8950
_shelx_estimated_absorpt_T_max   0.631
_shelx_estimated_absorpt_T_min   0.236
_exptl_absorpt_coefficient_mu    16.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1072
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16046
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.475
_diffrn_reflns_theta_max         67.475
_diffrn_reflns_theta_min         2.916
_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   -120.00 -40.00   0.50    0.05    --  -47.35 166.00  56.00  160
  2  ω    -64.00  22.00   0.50    0.05    --  -47.35  63.00  33.00  172
  3  ω   -123.00 -96.00   0.50    0.10    -- -106.00 -59.00  56.00   54
  4  ω    -69.00 -37.00   0.50    0.10    -- -106.00  63.00  33.00   64
  5  ω     47.00  72.00   0.50    0.10    --  113.25-115.00-178.00   50
  6  ω     42.00  68.00   0.50    0.10    --  113.25 -63.00-103.00   52
  7  ω    -27.00   6.00   0.50    0.05    --   47.35 -19.00   0.00   66
  8  ω    -64.00 -38.00   0.50    0.10    -- -106.00 125.00 150.00   52
  9  ω    -65.00 -40.00   0.50    0.10    -- -106.00  61.00  60.00   50
 10  ω    -67.00 -35.00   0.50    0.10    -- -106.00  61.00 -30.00   64
 11  ω   -109.00 -74.00   0.50    0.10    -- -106.00 125.00 150.00   70
 12  ω    101.00 177.00   0.50    0.10    --  113.25  15.00   0.00  152
 13  ω     42.00  67.00   0.50    0.10    --  113.25 -61.00-150.00   50
 14  ω     73.00 106.00   0.50    0.10    --  113.25 -94.00-150.00   66
 15  ω     42.00  67.00   0.50    0.10    --  113.25 -94.00-150.00   50
 16  ω     54.00  79.00   0.50    0.05    --   47.35-166.00  35.00   50
 17  ω   -118.00 -93.00   0.50    0.05    --  -47.35-125.00 120.00   50
 18  ω    -26.00  26.00   0.50    0.05    --   47.35 -19.00-120.00  104
 19  ω     -6.00  25.00   0.50    0.05    --   47.35 -19.00 150.00   62
 20  ω     74.00  99.00   0.50    0.05    --   47.35 125.00-180.00   50
 21  ω     77.00 117.00   0.50    0.05    --   47.35 125.00-120.00   80
 22  ω    -20.00  57.00   0.50    0.05    --   47.35 -57.00-150.00  154
 23  ω   -173.00-128.00   0.50    0.10    -- -106.00 -45.00 -90.00   90
 24  ω    -72.00 -46.00   0.50    0.10    -- -106.00 125.00  90.00   52
 25  ω   -108.00 -72.00   0.50    0.10    -- -106.00 114.00 167.36   72
 26  ω   -138.00 -85.00   0.50    0.10    -- -106.00 -94.00 -60.00  106
 27  ω   -174.00-148.00   0.50    0.10    -- -106.00 -94.00 -60.00   52
 28  ω    -65.00 -39.00   0.50    0.10    -- -106.00 114.00 167.36   52
 29  ω   -119.00 -45.00   0.50    0.10    -- -106.00 135.00 -86.11  148
 30  ω   -109.00 -83.00   0.50    0.10    -- -106.00 118.00  43.26   52
 31  ω    -70.00 -33.00   0.50    0.10    -- -106.00  61.00   0.00   74
 32  ω    -87.00 -38.00   0.50    0.10    -- -106.00 125.00-150.00   98
 33  ω   -109.00 -83.00   0.50    0.10    -- -106.00 115.00 -89.00   52
 34  ω   -121.00 -93.00   0.50    0.10    -- -106.00 -45.00  90.00   56
 35  ω   -174.00-104.00   0.50    0.10    -- -106.00 -45.00-180.00  140
 36  ω   -123.00 -73.00   0.50    0.10    -- -106.00 141.00  52.06  100
 37  ω    -70.00 -45.00   0.50    0.10    -- -106.00 141.00  52.06   50
 38  ω   -108.00 -76.00   0.50    0.10    -- -106.00 109.00 -14.63   64
 39  ω    -71.00 -46.00   0.50    0.10    -- -106.00  61.00 -60.00   50
 40  ω    -68.00 -36.00   0.50    0.10    -- -106.00 118.00  43.26   64
 41  ω   -123.00 -80.00   0.50    0.10    -- -106.00 141.00 162.56   86
;
_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      -0.2166389000
_diffrn_orient_matrix_UB_12      -0.0213948000
_diffrn_orient_matrix_UB_13      -0.1073090000
_diffrn_orient_matrix_UB_21      0.0547913000
_diffrn_orient_matrix_UB_22      0.0284253000
_diffrn_orient_matrix_UB_23      -0.1162080000
_diffrn_orient_matrix_UB_31      0.1704481000
_diffrn_orient_matrix_UB_32      -0.0363000000
_diffrn_orient_matrix_UB_33      -0.0279228000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2875
_reflns_number_total             2962
_reflns_odcompleteness_completeness 98.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.098
_refine_diff_density_min         -1.605
_refine_diff_density_rms         0.198
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.052
_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)+(0.0799P)²+0.0886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1077
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C11(H11), C12(H12), C4(H4), C15(H15), C2(H2), C9(H9),
 C14(H14), C13(H13)
;
_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 0.77025(4) 0.43339(2) 0.57950(2) 0.01319(14) Uani 1 1 d . . . . .
S1 S 0.10611(16) 0.45667(3) 0.29719(9) 0.0162(2) Uani 1 1 d . . . . .
F3 F 0.0542(6) 0.45008(10) 0.0289(3) 0.0393(6) Uani 1 1 d . . . . .
F1 F 0.3776(6) 0.41976(11) 0.1569(3) 0.0426(7) Uani 1 1 d . . . . .
F2 F 0.3565(6) 0.49047(9) 0.1373(4) 0.0470(8) Uani 1 1 d . . . . .
O1 O 0.3216(6) 0.45879(9) 0.4150(3) 0.0280(6) Uani 1 1 d . . . . .
O3 O -0.0354(5) 0.49729(8) 0.2758(3) 0.0241(6) Uani 1 1 d . . . . .
O2 O -0.0337(5) 0.41691(8) 0.2871(3) 0.0239(6) Uani 1 1 d . . . . .
N1 N 0.6933(5) 0.30030(9) 0.5250(3) 0.0147(6) Uani 1 1 d . . . . .
N2 N 0.4615(6) 0.30667(9) 0.4440(3) 0.0174(6) Uani 1 1 d . . . . .
C5 C 1.2368(7) 0.32240(11) 0.7268(4) 0.0155(7) Uani 1 1 d . . . . .
H5 H 1.2215 0.2915 0.7118 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6397(6) 0.37151(11) 0.5131(4) 0.0144(7) Uani 1 1 d . . . . .
C3 C 1.4749(7) 0.38521(12) 0.8368(4) 0.0198(8) Uani 1 1 d . . . . .
H3 H 1.6219 0.3964 0.8967 0.024 Uiso 1 1 calc R U . . .
C11 C 0.6815(7) 0.22955(11) 0.6379(4) 0.0179(7) Uani 1 1 d . . . . .
H11 H 0.5532 0.2403 0.6734 0.021 Uiso 1 1 calc R U . . .
C7 C 0.8097(7) 0.33919(12) 0.5694(4) 0.0132(7) Uani 1 1 d . . . . .
C6 C 1.0450(7) 0.35050(11) 0.6621(4) 0.0144(7) Uani 1 1 d . . . . .
C12 C 0.7692(7) 0.18674(12) 0.6673(4) 0.0203(8) Uani 1 1 d . . . . .
H12 H 0.7005 0.1680 0.7232 0.024 Uiso 1 1 calc R U . . .
C1 C 1.0778(6) 0.39578(11) 0.6873(4) 0.0145(7) Uani 1 1 d . . . . .
C4 C 1.4483(7) 0.33979(12) 0.8123(4) 0.0179(7) Uani 1 1 d . . . . .
H4 H 1.5785 0.3206 0.8555 0.022 Uiso 1 1 calc R U . . .
C10 C 0.7849(6) 0.25610(12) 0.5559(4) 0.0133(7) Uani 1 1 d . . . . .
C15 C 0.9727(6) 0.24131(12) 0.5030(4) 0.0160(7) Uani 1 1 d . . . . .
H15 H 1.0415 0.2600 0.4471 0.019 Uiso 1 1 calc R U . . .
C2 C 1.2879(7) 0.41401(12) 0.7741(4) 0.0176(7) Uani 1 1 d . . . . .
H2 H 1.3030 0.4449 0.7900 0.021 Uiso 1 1 calc R U . . .
C9 C 0.4282(7) 0.35040(11) 0.4371(4) 0.0149(7) Uani 1 1 d . . . . .
H9 H 0.2824 0.3649 0.3878 0.018 Uiso 1 1 calc R U . . .
C14 C 1.0585(7) 0.19833(12) 0.5339(4) 0.0195(8) Uani 1 1 d . . . . .
H14 H 1.1873 0.1875 0.4990 0.023 Uiso 1 1 calc R U . . .
C13 C 0.9559(7) 0.17157(11) 0.6153(4) 0.0205(8) Uani 1 1 d . . . . .
H13 H 1.0148 0.1423 0.6357 0.025 Uiso 1 1 calc R U . . .
C16 C 0.2309(8) 0.45417(13) 0.1468(5) 0.0268(9) 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 C8 2.060(3) . ?
I1 C1 2.122(3) . ?
S1 O1 1.453(3) . ?
S1 O3 1.455(3) . ?
S1 O2 1.433(3) . ?
S1 C16 1.823(4) . ?
F3 C16 1.331(5) . ?
F1 C16 1.323(5) . ?
F2 C16 1.329(5) . ?
N1 N2 1.362(4) . ?
N1 C7 1.366(5) . ?
N1 C10 1.440(4) . ?
N2 C9 1.338(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(5) . ?
C5 C4 1.379(5) . ?
C8 C7 1.385(5) . ?
C8 C9 1.393(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(5) . ?
C3 C2 1.388(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(5) . ?
C11 C10 1.385(5) . ?
C7 C6 1.448(5) . ?
C6 C1 1.399(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(6) . ?
C1 C2 1.388(5) . ?
C4 H4 0.9500 . ?
C10 C15 1.386(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.396(5) . ?
C2 H2 0.9500 . ?
C9 H9 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.382(6) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 I1 C1 81.41(14) . . ?
O1 S1 O3 113.22(16) . . ?
O1 S1 C16 103.6(2) . . ?
O3 S1 C16 103.73(19) . . ?
O2 S1 O1 115.20(17) . . ?
O2 S1 O3 115.26(17) . . ?
O2 S1 C16 103.83(18) . . ?
N2 N1 C7 112.2(3) . . ?
N2 N1 C10 119.7(3) . . ?
C7 N1 C10 128.1(3) . . ?
C9 N2 N1 105.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(3) . . ?
C7 C8 I1 111.2(3) . . ?
C7 C8 C9 107.6(3) . . ?
C9 C8 I1 141.0(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.7(3) . . ?
N1 C7 C8 104.7(3) . . ?
N1 C7 C6 134.0(3) . . ?
C8 C7 C6 121.1(3) . . ?
C5 C6 C7 128.5(3) . . ?
C5 C6 C1 117.7(3) . . ?
C1 C6 C7 113.7(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C6 C1 I1 112.6(3) . . ?
C2 C1 I1 123.8(3) . . ?
C2 C1 C6 123.6(3) . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C11 C10 N1 118.6(3) . . ?
C11 C10 C15 121.9(3) . . ?
C15 C10 N1 119.4(3) . . ?
C10 C15 H15 120.7 . . ?
C10 C15 C14 118.5(3) . . ?
C14 C15 H15 120.7 . . ?
C3 C2 H2 121.4 . . ?
C1 C2 C3 117.3(3) . . ?
C1 C2 H2 121.4 . . ?
N2 C9 C8 109.7(3) . . ?
N2 C9 H9 125.1 . . ?
C8 C9 H9 125.1 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
F3 C16 S1 111.1(3) . . ?
F1 C16 S1 110.3(3) . . ?
F1 C16 F3 107.8(3) . . ?
F1 C16 F2 108.5(4) . . ?
F2 C16 S1 111.1(3) . . ?
F2 C16 F3 107.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C8 C7 N1 175.8(2) . . . . ?
I1 C8 C7 C6 -0.1(4) . . . . ?
I1 C8 C9 N2 -174.1(3) . . . . ?
I1 C1 C2 C3 -179.5(3) . . . . ?
O1 S1 C16 F3 177.2(3) . . . . ?
O1 S1 C16 F1 57.8(3) . . . . ?
O1 S1 C16 F2 -62.7(3) . . . . ?
O3 S1 C16 F3 -64.3(3) . . . . ?
O3 S1 C16 F1 176.2(3) . . . . ?
O3 S1 C16 F2 55.8(3) . . . . ?
O2 S1 C16 F3 56.5(3) . . . . ?
O2 S1 C16 F1 -62.9(3) . . . . ?
O2 S1 C16 F2 176.6(3) . . . . ?
N1 N2 C9 C8 0.4(4) . . . . ?
N1 C7 C6 C5 6.1(7) . . . . ?
N1 C7 C6 C1 -174.2(4) . . . . ?
N1 C10 C15 C14 -179.9(3) . . . . ?
N2 N1 C7 C8 0.3(4) . . . . ?
N2 N1 C7 C6 175.4(4) . . . . ?
N2 N1 C10 C11 -66.6(5) . . . . ?
N2 N1 C10 C15 113.3(4) . . . . ?
C5 C6 C1 I1 179.4(3) . . . . ?
C5 C6 C1 C2 -1.0(5) . . . . ?
C8 C7 C6 C5 -179.5(4) . . . . ?
C8 C7 C6 C1 0.3(5) . . . . ?
C11 C12 C13 C14 0.1(6) . . . . ?
C11 C10 C15 C14 0.1(5) . . . . ?
C7 N1 N2 C9 -0.4(4) . . . . ?
C7 N1 C10 C11 112.1(4) . . . . ?
C7 N1 C10 C15 -67.9(5) . . . . ?
C7 C8 C9 N2 -0.2(4) . . . . ?
C7 C6 C1 I1 -0.3(4) . . . . ?
C7 C6 C1 C2 179.2(3) . . . . ?
C6 C5 C4 C3 0.4(5) . . . . ?
C6 C1 C2 C3 1.0(6) . . . . ?
C12 C11 C10 N1 179.7(3) . . . . ?
C12 C11 C10 C15 -0.2(5) . . . . ?
C4 C5 C6 C7 -180.0(4) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C4 C3 C2 C1 -0.2(6) . . . . ?
C10 N1 N2 C9 178.5(3) . . . . ?
C10 N1 C7 C8 -178.6(3) . . . . ?
C10 N1 C7 C6 -3.4(7) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C10 C15 C14 C13 0.1(5) . . . . ?
C15 C14 C13 C12 -0.2(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C9 C8 C7 N1 0.0(4) . . . . ?
C9 C8 C7 C6 -175.9(3) . . . . ?

_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 1.709
_oxdiff_exptl_absorpt_empirical_full_min 0.628
