# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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]I
_database_code_depnum_ccdc_archive 'CCDC 2085430'
loop_
_audit_author_name
_audit_author_address
'Vitalii Suslonov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2021-05-24 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;
_audit_creation_date             2021-05-24
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 I N2, I'
_chemical_formula_sum            'C12 H14 I2 N2'
_chemical_formula_weight         440.05
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N2 I C16 H10 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.7742(2)
_cell_length_b                   7.18240(10)
_cell_length_c                   15.7199(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1442.29(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14998
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.3360
_cell_measurement_theta_min      3.3930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    34.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
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    2.027
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25810
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.979
_diffrn_reflns_theta_min         4.460
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00 -14.00   0.50    0.24    --  -38.95  77.00-107.00  100
  2  ω     89.00 127.00   0.50    0.96    --  100.00 -77.00 127.00   76
  3  ω    131.00 157.00   0.50    0.96    --  100.00  77.00-107.00   52
  4  ω     83.00 123.00   0.50    0.96    --  100.00  77.00-107.00   80
  5  ω    -88.00 -55.00   0.50    0.24    --  -38.95 -43.00 -90.00   66
  6  ω    -54.00 -29.00   0.50    0.24    --  -38.95  43.00-120.00   50
  7  ω    -62.00 -16.00   0.50    0.24    --  -38.95  65.00   0.00   92
  8  ω    -95.00 -16.00   0.50    0.24    --  -38.95 138.00 -30.00  158
  9  ω    -75.00 -31.00   0.50    0.24    --  -38.95 -43.00  30.00   88
 10  ω    -52.00   4.00   0.50    0.24    --  -38.95  32.00 -60.00  112
 11  ω      1.00  26.00   0.50    0.24    --  -38.95  65.00   0.00   50
 12  ω    -27.00  -2.00   0.50    0.24    --  -38.95  43.00-120.00   50
 13  ω    -47.00 -22.00   0.50    0.24    --  -38.95 -43.00 -90.00   50
 14  ω    -18.00  41.00   0.50    0.24    --   38.95 -43.00  60.00  118
 15  ω     36.00  61.00   0.50    0.24    --   38.95 -77.00 127.00   50
 16  ω     -4.00  21.00   0.50    0.24    --   38.95 -77.00 127.00   50
 17  ω     78.00 105.00   0.50    0.96    --  100.00 -93.00-150.00   54
 18  ω     28.00  57.00   0.50    0.96    --  100.00 -93.00-150.00   58
 19  ω     97.00 123.00   0.50    0.96    --  100.00  30.00   0.00   52
 20  ω     75.00 100.00   0.50    0.96    --  100.00  15.00 150.00   50
 21  ω     36.00  61.00   0.50    0.96    --  100.00 -69.00-120.00   50
 22  ω     86.00 122.00   0.50    0.96    --  100.00 -61.00 -60.00   72
 23  ω     86.00 157.00   0.50    0.96    --  100.00  45.00-180.00  142
 24  ω     89.00 114.00   0.50    0.96    --  100.00 -30.00 -30.00   50
 25  ω     56.00  84.00   0.50    0.96    --  100.00 -30.00 -30.00   56
 26  ω     87.00 117.00   0.50    0.96    --  100.00 178.00  60.00   60
 27  ω     33.00  98.00   0.50    0.96    --  100.00 -37.00  90.00  130
 28  ω     71.00 125.00   0.50    0.96    --  100.00 -69.00-120.00  108
 29  ω     30.00 107.00   0.50    0.96    --  100.00 -22.00 150.00  154
 30  ω    106.00 157.00   0.50    0.96    --  100.00  15.00 150.00  102
 31  ω     54.00  80.00   0.50    0.96    --  100.00 178.00  60.00   52
 32  ω     72.00  99.00   0.50    0.96    --  100.00 -77.00   0.00   54
 33  ω     38.00  66.00   0.50    0.96    --  100.00 -86.00 120.00   56
 34  ω     46.00 122.00   0.50    0.96    --  100.00 -61.00 120.00  152
 35  ω     34.00  62.00   0.50    0.96    --  100.00 -77.00   0.00   56
 36  ω    109.00 140.00   0.50    0.96    --  100.00  69.00-120.00   62
 37  ω     54.00  79.00   0.50    0.96    --  100.00 -22.00 140.48   50
 38  ω     65.00 100.00   0.50    0.96    --  100.00  10.00  38.89   70
 39  ω     85.00 143.00   0.50    0.96    --  100.00  93.00-150.00  116
 40  ω    -69.00 -36.00   0.50    0.24    --  -38.95 102.00 140.00   66
 41  ω    -42.00 -12.00   0.50    0.24    --    0.00 120.00 -93.84   60
 42  ω    -30.00  -4.00   0.50    0.24    --   16.00 117.00  30.13   52
 43  ω    -12.00  13.00   0.50    0.24    --   24.00 101.00 -90.69   50
 44  ω    -13.00  12.00   0.50    0.24    --   24.00 102.00 128.18   50
 45  ω     -5.00  20.00   0.50    0.24    --   28.00  92.00  10.01   50
 46  ω      1.00  26.00   0.50    0.24    --   32.00  89.00 -59.34   50
 47  ω      1.00  26.00   0.50    0.24    --   32.00  88.00-137.69   50
 48  ω      1.00  26.00   0.50    0.24    --   32.00  88.00 179.86   50
 49  ω      7.00  32.00   0.50    0.24    --   36.00  83.00-106.42   50
 50  ω      7.00  32.00   0.50    0.24    --   36.00  83.00 109.26   50
 51  ω    -12.00  13.00   0.50    0.24    --  -38.95 102.00 140.00   50
 52  ω     12.00  37.00   0.50    0.24    --   40.00  80.00 -84.64   50
 53  ω     12.00  37.00   0.50    0.24    --   40.00  80.00  47.48   50
 54  ω     12.00  37.00   0.50    0.24    --   40.00  80.00  88.69   50
 55  ω     16.00  41.00   0.50    0.24    --   44.00  81.00 134.20   50
 56  ω     16.00  41.00   0.50    0.24    --   44.00  82.00  11.24   50
 57  ω     16.00  41.00   0.50    0.24    --   44.00  81.00 -33.86   50
 58  ω     16.00  41.00   0.50    0.24    --   44.00  80.00 -79.07   50
 59  ω     16.00  41.00   0.50    0.24    --   44.00  81.00-161.15   50
 60  ω     16.00  41.00   0.50    0.24    --   44.00  82.00 159.59   50
 61  ω     30.00  58.00   0.50    0.24    --   48.00  72.00 158.55   56
 62  ω     23.00  52.00   0.50    0.24    --   48.00  73.00 101.77   58
 63  ω     27.00  60.00   0.50    0.24    --   52.00  73.00 -82.47   66
 64  ω     26.00  52.00   0.50    0.24    --   52.00  74.00  38.85   52
 65  ω     46.00  71.00   0.50    0.24    --   60.00  65.00  37.55   50
 66  ω     37.00  70.00   0.50    0.24    --   60.00  67.00-150.45   66
 67  ω     37.00  89.00   0.50    0.24    --   60.00  73.00 175.83  104
 68  ω     45.00 101.00   0.50    0.24    --   60.00  72.00 121.44  112
 69  ω     71.00  97.00   0.50    0.24    --   60.00  67.00-150.45   52
 70  ω     39.00 103.00   0.50    0.24    --   64.00  72.00-133.72  128
 71  ω     39.00  64.00   0.50    0.24    --   64.00  73.00 -49.05   50
 72  ω    100.00 127.00   0.50    0.24    --   64.00  73.00 -49.05   54
 73  ω     86.00 134.00   0.50    0.24    --   68.00  67.00  57.28   96
 74  ω     44.00  79.00   0.50    0.24    --   68.00  67.00  57.28   70
 75  ω     45.00  76.00   0.50    0.24    --   68.00  74.00  -6.89   62
 76  ω     48.00  79.00   0.50    0.96    --   72.00  67.00 -92.04   62
 77  ω     47.00  73.00   0.50    0.96    --   72.00  70.00 101.63   52
 78  ω     47.00  72.00   0.50    0.96    --   72.00  71.00 -15.66   50
 79  ω    107.00 137.00   0.50    0.96    --   76.00  73.00 131.42   60
 80  ω     53.00  80.00   0.50    0.96    --   76.00  65.00 -83.86   54
 81  ω     51.00  79.00   0.50    0.96    --   76.00  70.00 -50.82   56
 82  ω     55.00  91.00   0.50    0.96    --   76.00  56.00-102.26   72
 83  ω     58.00  90.00   0.50    0.96    --   76.00  57.00  31.97   64
 84  ω     53.00 113.00   0.50    0.96    --   76.00  69.00 114.32  120
 85  ω     55.00 104.00   0.50    0.96    --   76.00  73.00 131.42   98
 86  ω     59.00 143.00   0.50    0.96    --   80.00  57.00-170.36  168
 87  ω     63.00  92.00   0.50    0.96    --   84.00  56.00-120.86   58
 88  ω     62.00  98.00   0.50    0.96    --   84.00  70.00  -7.76   72
 89  ω     96.00 123.00   0.50    0.96    --   88.00  70.00 -67.93   54
 90  ω     63.00  88.00   0.50    0.96    --   88.00  70.00 -67.93   50
 91  ω     83.00 132.00   0.50    0.96    --  100.00  77.00 -30.00   98
 92  ω     76.00 129.00   0.50    0.96    --  100.00  69.00 120.00  106
 93  ω     61.00 108.00   0.50    0.96    --  100.00-111.00  60.00   94
 94  ω     48.00  97.00   0.50    0.96    --  100.00 178.00   0.00   98
 95  ω    127.00 153.00   0.50    0.96    --  100.00  69.00 -30.00   52
 96  ω     91.00 117.00   0.50    0.96    --  100.00 -77.00  60.00   52
 97  ω    118.00 144.00   0.50    0.96    --  100.00 178.00   0.00   52
 98  ω     76.00 107.00   0.50    0.96    --  100.00  69.00  30.00   62
 99  ω     77.00 102.00   0.50    0.96    --  100.00  69.00 -30.00   50
100  ω     45.00  71.00   0.50    0.96    --  100.00 -77.00  60.00   52
101  ω     85.00 151.00   0.50    0.96    --  100.00  77.00  90.00  132
102  ω     87.00 147.00   0.50    0.96    --  100.00  77.00 -90.00  120
103  ω     69.00 102.00   0.50    0.96    --  100.00 -93.00 120.00   66
104  ω     65.00  91.00   0.50    0.96    --  100.00 -15.00   0.00   52
105  ω     66.00  94.00   0.50    0.96    --  100.00-133.00  30.00   56
106  ω     27.00  52.00   0.50    0.96    --  100.00 -93.00 120.00   50
107  ω     37.00  63.00   0.50    0.96    --  100.00-133.00  30.00   52
108  ω    131.00 157.00   0.50    0.96    --  100.00  37.00 -30.00   52
109  ω     94.00 119.00   0.50    0.96    --  100.00  37.00 -30.00   50
110  ω    126.00 154.00   0.50    0.96    --  100.00  69.00 150.00   56
111  ω     78.00 104.00   0.50    0.96    --  100.00  61.00  60.00   52
112  ω     83.00 115.00   0.50    0.96    --  100.00  77.00 -60.00   64
113  ω    132.00 157.00   0.50    0.96    --  100.00  69.00 -60.00   50
114  ω     78.00 104.00   0.50    0.96    --  100.00  69.00 150.00   52
115  ω     87.00 113.00   0.50    0.96    --  100.00 -37.00 -30.00   52
116  ω     36.00  66.00   0.50    0.96    --  100.00 -37.00 -30.00   60
117  ω     79.00 105.00   0.50    0.96    --  100.00  61.00  90.00   52
118  ω     57.00 108.00   0.50    0.96    --  100.00 -30.00-120.00  102
119  ω     81.00 109.00   0.50    0.96    --  100.00 -45.00-180.00   56
120  ω     37.00  68.00   0.50    0.96    --  100.00 -45.00-180.00   62
121  ω     76.00 132.00   0.50    0.96    --  100.00  69.00-150.00  112
122  ω     76.00 139.00   0.50    0.96    --  100.00  69.00   0.00  126
123  ω     80.00 108.00   0.50    0.96    --  100.00-111.00 -30.00   56
124  ω     31.00  64.00   0.50    0.96    --  100.00-111.00 -30.00   66
125  ω     81.00 155.00   0.50    0.96    --  100.00  53.00  60.00  148
126  ω     80.00 106.00   0.50    0.96    --  100.00  53.00-180.00   52
127  ω     93.00 118.00   0.50    0.96    --  100.00-133.00 -30.00   50
128  ω     58.00 104.00   0.50    0.96    --  100.00-111.00  30.00   92
129  ω     38.00  85.00   0.50    0.96    --  100.00-133.00 -30.00   94
130  ω     77.00 102.00   0.50    0.96    --  100.00  69.00 -60.00   50
131  ω     77.00 104.00   0.50    0.96    --  100.00  69.00-120.00   54
132  ω     83.00 108.00   0.50    0.96    --  100.00-111.00-150.00   50
133  ω     37.00  63.00   0.50    0.96    --  100.00-111.00-150.00   52
134  ω    121.00 148.00   0.50    0.96    --  100.00  65.00  12.50   54
135  ω    120.00 157.00   0.50    0.96    --  100.00  69.00-180.00   74
136  ω     77.00 103.00   0.50    0.96    --  100.00  65.00  12.50   52
137  ω     76.00 108.00   0.50    0.96    --  100.00  69.00-180.00   64
138  ω     80.00 129.00   0.50    0.96    --  100.00  53.00-150.00   98
139  ω    113.00 138.00   0.50    0.96    --  100.00  61.00 150.00   50
140  ω     26.00  52.00   0.50    0.96    --  100.00 -15.00   0.00   52
141  ω     78.00 104.00   0.50    0.96    --  100.00  61.00 150.00   52
142  ω    104.00 129.00   0.50    0.96    --  100.00 -15.00   0.00   50
143  ω    113.00 154.00   0.50    0.96    --  100.00  61.00  30.00   82
144  ω    124.00 149.00   0.50    0.96    --  100.00  53.00  90.00   50
145  ω     80.00 106.00   0.50    0.96    --  100.00  53.00  90.00   52
146  ω     78.00 104.00   0.50    0.96    --  100.00  61.00  30.00   52
147  ω     45.00 108.00   0.50    0.96    --  100.00-111.00 120.00  126
;
_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      -0.0997903000
_diffrn_orient_matrix_UB_12      0.0018289000
_diffrn_orient_matrix_UB_13      0.1203842000
_diffrn_orient_matrix_UB_21      -0.0178432000
_diffrn_orient_matrix_UB_22      0.0937654000
_diffrn_orient_matrix_UB_23      -0.0535830000
_diffrn_orient_matrix_UB_31      -0.0653326000
_diffrn_orient_matrix_UB_32      -0.0284133000
_diffrn_orient_matrix_UB_33      -0.1692589000
_diffrn_oxdiff_ac3_digest_frames 
;
01185852d6d990fd45a62bf378ba48738f0003498a1
;
_diffrn_oxdiff_ac3_digest_hkl    
;
015dac30ce55cb710e2898bb2a92c7c626053f
;
_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                1434
_reflns_number_total             1483
_reflns_odcompleteness_completeness 98.85
_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 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_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         1.530
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0216
_refine_ls_restrained_S_all      1.062
_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)+(0.0280P)²+2.3930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0535
_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. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H9A(0.5) H9B(0.5) H9C(0.5) H4A(0.5) H4B(0.5)
 H4C(0.5)
3.a Riding coordinates:
 C10(H10A,H10B,H10C)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C7(H7)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.60811(2) 0.7500 0.60327(2) 0.01605(10) Uani 1 2 d S T P . .
I2 I 0.67451(2) 0.7500 0.81120(2) 0.02196(10) Uani 1 2 d S T P . .
N1 N 0.4496(3) 0.7500 0.3666(2) 0.0155(7) Uani 1 2 d S T P . .
N2 N 0.5503(3) 0.7500 0.3366(2) 0.0154(7) Uani 1 2 d S T P . .
C10 C 0.3544(4) 0.7500 0.5041(3) 0.0223(9) Uani 1 2 d S T P . .
H10A H 0.3149 0.8609 0.4926 0.033 Uiso 0.5 1 d R . . A -1
H10B H 0.3129 0.6428 0.4902 0.033 Uiso 0.5 1 d R . . A -1
H10C H 0.3726 0.7500 0.5633 0.033 Uiso 0.5 1 d RS T P A -1
C1 C 0.5559(3) 0.7500 0.4766(2) 0.0144(8) Uani 1 2 d S T P . .
C3 C 0.4513(3) 0.7500 0.4520(2) 0.0143(8) Uani 1 2 d S T P . .
C9 C 0.3602(3) 0.7500 0.3085(3) 0.0177(8) Uani 1 2 d S T P . .
H9A H 0.3688 0.6502 0.2665 0.027 Uiso 0.5 1 calc GR . . B -1
H9B H 0.3564 0.8702 0.2791 0.027 Uiso 0.5 1 calc GR . . B -1
H9C H 0.2956 0.7296 0.3408 0.027 Uiso 0.5 1 calc GR . . B -1
C2 C 0.6172(3) 0.7500 0.4032(2) 0.0157(8) Uani 1 2 d S T P . .
C5 C 0.5709(3) 0.7500 0.2460(2) 0.0199(9) Uani 1 2 d S T P . .
C4 C 0.7325(3) 0.7500 0.3920(2) 0.0200(9) Uani 1 2 d S T P . .
H4A H 0.7525 0.6503 0.3527 0.030 Uiso 0.5 1 calc GR . . C -1
H4B H 0.7663 0.7295 0.4472 0.030 Uiso 0.5 1 calc GR . . C -1
H4C H 0.7548 0.8702 0.3688 0.030 Uiso 0.5 1 calc GR . . C -1
C8 C 0.5921(4) 0.7500 0.0729(3) 0.0468(18) Uani 1 2 d S T P . .
H8 H 0.5982 0.7500 0.0127 0.056 Uiso 1 2 calc RS T P . .
C6 C 0.5769(3) 0.9188(6) 0.2044(2) 0.0347(8) Uani 1 1 d . . . . .
H6 H 0.5738 1.0329 0.2349 0.042 Uiso 1 1 calc R . . . .
C7 C 0.5878(3) 0.9163(8) 0.1162(2) 0.0488(12) Uani 1 1 d . . . . .
H7 H 0.5923 1.0303 0.0857 0.059 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.100(4) . ?
N1 N2 1.370(5) . ?
N1 C3 1.344(5) . ?
N1 C9 1.462(5) . ?
N2 C2 1.352(5) . ?
N2 C5 1.448(5) . ?
C10 H10A 0.9601 . ?
C10 H10B 0.9601 . ?
C10 H10C 0.9594 . ?
C10 C3 1.485(6) . ?
C1 C3 1.391(6) . ?
C1 C2 1.394(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C2 C4 1.483(6) . ?
C5 C6 1.380(4) . ?
C5 C6 1.380(4) 7_575 ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C7 1.376(6) 7_575 ?
C8 C7 1.376(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(5) . ?
C7 H7 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
N2 N1 C9 121.2(3) . . ?
C3 N1 N2 109.2(3) . . ?
C3 N1 C9 129.6(3) . . ?
N1 N2 C5 120.6(3) . . ?
C2 N2 N1 109.1(3) . . ?
C2 N2 C5 130.3(3) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 108.1 . . ?
H10B C10 H10C 110.8 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.4 . . ?
C3 C1 I1 124.6(3) . . ?
C3 C1 C2 108.1(3) . . ?
C2 C1 I1 127.3(3) . . ?
N1 C3 C10 122.5(4) . . ?
N1 C3 C1 107.0(3) . . ?
C1 C3 C10 130.4(4) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C2 C1 106.6(3) . . ?
N2 C2 C4 122.4(3) . . ?
C1 C2 C4 131.0(4) . . ?
C6 C5 N2 118.4(2) . . ?
C6 C5 N2 118.4(2) 7_575 . ?
C6 C5 C6 123.0(4) 7_575 . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 H8 119.8 7_575 . ?
C7 C8 C7 120.5(5) . 7_575 ?
C5 C6 H6 121.1 . . ?
C5 C6 C7 117.8(4) . . ?
C7 C6 H6 121.1 . . ?
C8 C7 C6 120.5(4) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?

_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 1.800
_oxdiff_exptl_absorpt_empirical_full_min 0.671
####################################################################### 
# 
# 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]OTf
_database_code_depnum_ccdc_archive 'CCDC 2085431'
loop_
_audit_author_name
_audit_author_address
'Vitalii Suslonov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2021-05-24 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;
_audit_creation_date             2021-05-24
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 F3 I N2 O3 S'
_chemical_formula_sum            'C13 H14 F3 I N2 O3 S'
_chemical_formula_weight         462.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H10 N2 I1 S1 O3 F3'
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                   8.3762(4)
_cell_length_b                   14.1584(7)
_cell_length_c                   14.0266(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.152(4)
_cell_angle_gamma                90
_cell_volume                     1650.52(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11193
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2960
_cell_measurement_theta_min      4.4530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.860
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_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  0.0506
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16922
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.989
_diffrn_reflns_theta_min         4.455
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  67.00   0.50    0.06    --   47.20 -71.00  69.00  182
  2  ω     39.00  85.00   0.50    0.22    --  107.75 -71.00  69.00   92
  3  ω     76.00 106.00   0.50    0.22    --  107.75 -77.00 120.00   60
  4  ω     45.00  71.00   0.50    0.22    --  107.75 -61.00   0.00   52
  5  ω     38.00  70.00   0.50    0.22    --  107.75 -61.00 -30.00   64
  6  ω     36.00  62.00   0.50    0.22    --  107.75 -61.00 -90.00   52
  7  ω     41.00  97.00   0.50    0.22    --  107.75 -94.00-150.00  112
  8  ω     76.00 104.00   0.50    0.22    --  107.75 -94.00-120.00   56
  9  ω     35.00  60.00   0.50    0.22    --  107.75 -61.00-120.00   50
 10  ω     35.00  69.00   0.50    0.22    --  107.75 -61.00-150.00   68
 11  ω    141.00 177.00   0.50    0.22    --  107.75  45.00 -30.00   72
 12  ω    116.00 165.00   0.50    0.22    --  107.75  71.00-159.00   98
 13  ω     95.00 135.00   0.50    0.22    --  107.75  45.00 -30.00   80
 14  ω     75.00 115.00   0.50    0.06    --   47.20 125.00  60.00   80
 15  ω     74.00 120.00   0.50    0.06    --   47.20 125.00  30.00   92
 16  ω    134.00 160.00   0.50    0.22    --  107.75  30.00 150.00   52
 17  ω     97.00 173.00   0.50    0.22    --  107.75  15.00 120.00  152
 18  ω     49.00  74.00   0.50    0.06    --   47.20  71.00-159.00   50
 19  ω     42.00  71.00   0.50    0.22    --  107.75 -61.00  90.00   58
 20  ω    -60.00   6.00   0.50    0.06    --  -47.20  71.00-159.00  132
 21  ω    -58.00 -33.00   0.50    0.22    -- -106.00  61.00-180.00   50
 22  ω    -72.00 -46.00   0.50    0.22    -- -106.00  71.00-159.00   52
 23  ω   -121.00 -93.00   0.50    0.22    -- -106.00 -15.00 -60.00   56
 24  ω    -71.00 -46.00   0.50    0.22    -- -106.00  61.00  30.00   50
 25  ω    -97.00 -35.00   0.50    0.22    -- -106.00  77.00 150.00  124
 26  ω    -95.00 -42.00   0.50    0.06    --  -47.20 -71.00  69.00  106
 27  ω   -129.00 -83.00   0.50    0.22    -- -106.00 -77.00 150.00   92
 28  ω   -162.00-132.00   0.50    0.22    -- -106.00 -71.00  69.00   60
 29  ω   -175.00-149.00   0.50    0.22    -- -106.00 -77.00 150.00   52
 30  ω   -177.00-130.00   0.50    0.22    -- -106.00 -15.00 -60.00   94
 31  ω   -177.00-107.00   0.50    0.22    -- -106.00 -30.00-120.00  140
 32  ω    -85.00 -40.00   0.50    0.22    -- -106.00  71.00-159.00   90
 33  ω   -120.00 -94.00   0.50    0.06    --  -47.20-125.00 -30.00   52
 34  ω    -20.00  16.00   0.50    0.06    --   47.20 -19.00 150.00   72
 35  ω    -27.00  10.00   0.50    0.06    --   47.20 -19.00  90.00   74
 36  ω     39.00  70.00   0.50    0.06    --   47.20  37.00 -30.00   62
 37  ω     75.00 119.00   0.50    0.06    --   47.20  37.00 -30.00   88
 38  ω   -172.00-145.00   0.50    0.22    -- -106.00 -77.00-180.00   54
 39  ω   -123.00 -97.00   0.50    0.22    -- -106.00 -15.00  60.00   52
 40  ω   -164.00-139.00   0.50    0.22    -- -106.00 -61.00 -30.00   50
 41  ω   -168.00-130.00   0.50    0.22    -- -106.00 -61.00   0.00   76
 42  ω   -120.00 -73.00   0.50    0.22    -- -106.00-125.00  30.00   94
;
_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      0.0042071000
_diffrn_orient_matrix_UB_12      0.0609425000
_diffrn_orient_matrix_UB_13      0.0912634000
_diffrn_orient_matrix_UB_21      0.1370209000
_diffrn_orient_matrix_UB_22      -0.0616779000
_diffrn_orient_matrix_UB_23      0.0501166000
_diffrn_orient_matrix_UB_31      0.1247031000
_diffrn_orient_matrix_UB_32      0.0657582000
_diffrn_orient_matrix_UB_33      -0.0376266000
_diffrn_oxdiff_digest_frames     
;
01614d02cec8e7c926059f083e7597e60900089f093
;
_diffrn_oxdiff_digest_hkl        
;
0171b188a8a7df1dd9fb761050663d8ed4e62c
;
_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                3031
_reflns_number_total             3129
_reflns_odcompleteness_completeness 99.86
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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         0.612
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.049
_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)+(0.0378P)²+0.9776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0659
_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), C8(H8), C7(H7), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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 0.14289(2) 0.96848(2) 0.30177(2) 0.02425(8) Uani 1 1 d . . . . .
S1 S -0.30707(7) 1.10891(4) 0.25972(4) 0.01742(13) Uani 1 1 d . . . . .
F2 F -0.2682(2) 1.19887(12) 0.10066(11) 0.0335(4) Uani 1 1 d . . . . .
F3 F -0.0479(2) 1.16581(14) 0.18978(14) 0.0424(5) Uani 1 1 d . . . . .
O1 O -0.2204(2) 1.03027(12) 0.30724(15) 0.0240(4) Uani 1 1 d . . . . .
O3 O -0.2943(2) 1.19592(13) 0.31276(13) 0.0264(4) Uani 1 1 d . . . . .
F1 F -0.1778(3) 1.05708(14) 0.10684(14) 0.0543(6) Uani 1 1 d . . . . .
O2 O -0.4653(2) 1.08770(15) 0.21372(18) 0.0402(5) Uani 1 1 d . . . . .
N2 N 0.5892(2) 0.83278(14) 0.36716(14) 0.0166(4) Uani 1 1 d . . . . .
N1 N 0.5830(2) 0.83718(14) 0.26933(14) 0.0172(4) Uani 1 1 d . . . . .
C1 C 0.3667(3) 0.90548(16) 0.31024(18) 0.0169(4) Uani 1 1 d . . . . .
C6 C 0.7316(3) 0.69534(17) 0.44045(18) 0.0205(5) Uani 1 1 d . . . . .
H6 H 0.6518 0.6550 0.4082 0.025 Uiso 1 1 calc R . . . .
C5 C 0.7232(3) 0.79247(17) 0.42769(16) 0.0171(5) Uani 1 1 d . . . . .
C2 C 0.4570(3) 0.87507(16) 0.39349(17) 0.0166(5) Uani 1 1 d . . . . .
C8 C 0.9745(3) 0.7185(2) 0.54831(18) 0.0240(5) Uani 1 1 d . . . . .
H8 H 1.0609 0.6929 0.5908 0.029 Uiso 1 1 calc R . . . .
C7 C 0.8595(3) 0.65868(18) 0.50128(19) 0.0237(5) Uani 1 1 d . . . . .
H7 H 0.8684 0.5924 0.5108 0.028 Uiso 1 1 calc R . . . .
C4 C 0.4275(3) 0.87991(18) 0.49563(17) 0.0212(5) Uani 1 1 d . . . . .
H4A H 0.3943 0.8176 0.5164 0.032 Uiso 1 1 calc GR . . . .
H4B H 0.3422 0.9260 0.5023 0.032 Uiso 1 1 calc GR . . . .
H4C H 0.5264 0.8994 0.5355 0.032 Uiso 1 1 calc GR . . . .
C9 C 0.9649(3) 0.81540(19) 0.53407(19) 0.0239(5) Uani 1 1 d . . . . .
H9 H 1.0444 0.8558 0.5665 0.029 Uiso 1 1 calc R . . . .
C3 C 0.4481(3) 0.88098(16) 0.23286(17) 0.0170(5) Uani 1 1 d . . . . .
C10 C 0.8387(3) 0.85303(18) 0.47236(18) 0.0203(5) Uani 1 1 d . . . . .
H10 H 0.8318 0.9191 0.4610 0.024 Uiso 1 1 calc R . . . .
C11 C 0.7081(3) 0.7940(2) 0.22040(19) 0.0282(6) Uani 1 1 d . . . . .
H11A H 0.8136 0.8176 0.2485 0.042 Uiso 1 1 calc GR . . . .
H11B H 0.6904 0.8102 0.1520 0.042 Uiso 1 1 calc GR . . . .
H11C H 0.7045 0.7253 0.2278 0.042 Uiso 1 1 calc GR . . . .
C12 C 0.4056(3) 0.89764(19) 0.12800(18) 0.0235(5) Uani 1 1 d . . . . .
H12A H 0.4990 0.9237 0.1013 0.035 Uiso 1 1 calc GR . . . .
H12B H 0.3159 0.9424 0.1177 0.035 Uiso 1 1 calc GR . . . .
H12C H 0.3740 0.8378 0.0960 0.035 Uiso 1 1 calc GR . . . .
C13 C -0.1942(3) 1.13375(19) 0.15934(19) 0.0260(6) 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 O1 3.176(2) . ?
I1 C1 2.066(2) . ?
S1 O1 1.4459(18) . ?
S1 O3 1.4362(19) . ?
S1 O2 1.432(2) . ?
S1 C13 1.825(3) . ?
F2 C13 1.336(3) . ?
F3 C13 1.327(4) . ?
F1 C13 1.328(3) . ?
N2 N1 1.368(3) . ?
N2 C5 1.438(3) . ?
N2 C2 1.350(3) . ?
N1 C3 1.333(3) . ?
N1 C11 1.457(3) . ?
C1 C2 1.379(3) . ?
C1 C3 1.396(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.388(3) . ?
C6 C7 1.384(4) . ?
C5 C10 1.383(4) . ?
C2 C4 1.486(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.387(4) . ?
C8 C9 1.387(4) . ?
C7 H7 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.386(4) . ?
C3 C12 1.488(3) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 I1 O1 169.31(7) . . ?
O1 S1 C13 103.03(12) . . ?
O3 S1 O1 114.91(12) . . ?
O3 S1 C13 102.83(12) . . ?
O2 S1 O1 115.45(12) . . ?
O2 S1 O3 114.72(13) . . ?
O2 S1 C13 103.41(14) . . ?
S1 O1 I1 128.95(10) . . ?
N1 N2 C5 122.65(18) . . ?
C2 N2 N1 108.92(19) . . ?
C2 N2 C5 128.37(19) . . ?
N2 N1 C11 120.9(2) . . ?
C3 N1 N2 109.30(18) . . ?
C3 N1 C11 129.7(2) . . ?
C2 C1 I1 125.58(18) . . ?
C2 C1 C3 108.1(2) . . ?
C3 C1 I1 126.18(18) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C7 C6 C5 118.3(2) . . ?
C6 C5 N2 119.5(2) . . ?
C10 C5 N2 118.2(2) . . ?
C10 C5 C6 122.3(2) . . ?
N2 C2 C1 106.8(2) . . ?
N2 C2 C4 121.7(2) . . ?
C1 C2 C4 131.5(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C9 C8 C7 120.7(2) . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
N1 C3 C1 106.8(2) . . ?
N1 C3 C12 122.7(2) . . ?
C1 C3 C12 130.5(2) . . ?
C5 C10 C9 118.7(2) . . ?
C5 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F2 C13 S1 111.31(18) . . ?
F3 C13 S1 111.34(19) . . ?
F3 C13 F2 107.5(2) . . ?
F3 C13 F1 107.6(2) . . ?
F1 C13 S1 111.7(2) . . ?
F1 C13 F2 107.1(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 1.344
_oxdiff_exptl_absorpt_empirical_full_min 0.762
####################################################################### 
# 
# 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_[1]I
_database_code_depnum_ccdc_archive 'CCDC 2085432'
loop_
_audit_author_name
_audit_author_address
'Vitalii Suslonov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2021-05-24 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;
_audit_creation_date             2021-05-24
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H12 I1.5 N2, 0.5(I)'
_chemical_formula_sum            'C7 H12 I2 N2'
_chemical_formula_weight         377.99
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H4 N2 I '
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.6499(2)
_cell_length_b                   16.45897(18)
_cell_length_c                   28.2119(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.4830(12)
_cell_angle_gamma                90
_cell_volume                     6771.38(15)
_cell_formula_units_Z            24
_cell_measurement_reflns_used    20202
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.3850
_cell_measurement_theta_min      3.1410
_shelx_estimated_absorpt_T_max   0.107
_shelx_estimated_absorpt_T_min   0.027
_exptl_absorpt_coefficient_mu    43.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
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    2.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             4176
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.093
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1082
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            38003
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.514
_diffrn_reflns_theta_min         3.147
_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 1.000
_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    -77.00 -40.00   0.50    0.41    --  -38.82 104.00  -9.00   74
  2  ω     20.00  51.00   0.50    0.41    --   38.82-104.00-110.00   62
  3  ω    106.00 132.00   0.50    1.63    --  100.00 104.00  -9.00   52
  4  ω     46.00 100.00   0.50    1.63    --  100.00-104.00-110.00  108
  5  ω   -111.00 -77.00   0.50    0.41    --  -38.82 -21.00 -90.00   68
  6  ω    -37.00   8.00   0.50    0.41    --  -38.82 104.00  -9.00   90
  7  ω    -73.00 -34.00   0.50    0.41    --  -38.82  11.00 150.00   78
  8  ω    -97.00 -19.00   0.50    0.41    --  -38.82 -65.00 -90.00  156
  9  ω    -20.00  36.00   0.50    0.41    --  -38.82  11.00 150.00  112
 10  ω    -73.00 -19.00   0.50    0.41    --  -38.82 -21.00 -90.00  108
 11  ω    -75.00 -13.00   0.50    0.41    --  -38.82 104.00  60.00  124
 12  ω     26.00  52.00   0.50    0.41    --   38.82  32.00-120.00   52
 13  ω     24.00  52.00   0.50    0.41    --   38.82-138.00 -30.00   56
 14  ω     62.00 107.00   0.50    0.41    --   38.82  32.00-120.00   90
 15  ω     61.00  86.00   0.50    0.41    --   38.82-138.00 -30.00   50
 16  ω     17.00  43.00   0.50    0.41    --   38.82 -32.00   0.00   52
 17  ω     27.00  52.00   0.50    0.41    --   38.82  32.00 -90.00   50
 18  ω    -25.00   0.00   0.50    0.41    --   38.82 -32.00   0.00   50
 19  ω     68.00 118.00   0.50    1.63    --  100.00 -53.00 -90.00  100
 20  ω     88.00 114.00   0.50    1.63    --  100.00  37.00  60.00   52
 21  ω     43.00  69.00   0.50    1.63    --  100.00 -30.00-150.00   52
 22  ω     26.00 105.00   0.50    1.63    --  100.00 -93.00 -90.00  158
 23  ω     35.00  85.00   0.50    1.63    --  100.00 -69.00 120.00  100
 24  ω    122.00 153.00   0.50    1.63    --  100.00  22.00 -90.00   62
 25  ω     37.00 118.00   0.50    1.63    --  100.00 -77.00 -90.00  162
 26  ω    110.00 147.00   0.50    1.63    --  100.00  61.00 150.00   74
 27  ω     82.00 118.00   0.50    1.63    --  100.00  22.00 -90.00   72
 28  ω     86.00 154.00   0.50    1.63    --  100.00  30.00 -30.00  136
 29  ω     90.00 117.00   0.50    1.63    --  100.00 -69.00 120.00   54
 30  ω     51.00 113.00   0.50    1.63    --  100.00 -30.00  30.00  124
 31  ω     60.00  85.00   0.50    1.63    --  100.00-111.00 -90.00   50
 32  ω    116.00 155.00   0.50    1.63    --  100.00  37.00  60.00   78
 33  ω     30.00  72.00   0.50    1.63    --  100.00 -93.00 -30.00   84
 34  ω    107.00 151.00   0.50    1.63    --  100.00 111.00   0.00   88
 35  ω    101.00 126.00   0.50    1.63    --  100.00  37.00 -60.00   50
 36  ω     88.00 151.00   0.50    1.63    --  100.00  30.00  30.00  126
 37  ω    129.00 156.00   0.50    1.63    --  100.00  77.00 120.00   54
 38  ω     47.00 121.00   0.50    1.63    --  100.00 -86.00  60.00  148
 39  ω     87.00 112.00   0.50    1.63    --  100.00 -30.00-150.00   50
 40  ω     87.00 113.00   0.50    1.63    --  100.00  22.00-180.00   52
 41  ω     30.00  55.00   0.50    1.63    --  100.00 -93.00  60.00   50
 42  ω    120.00 146.00   0.50    1.63    --  100.00 104.00  -9.00   52
 43  ω    -15.00  28.00   0.50    0.41    --  -38.82  32.00-120.00   86
 44  ω    -57.00  -6.00   0.50    0.41    --  -38.82  21.00   0.00  102
 45  ω    -49.00  21.00   0.50    0.41    --  -38.82  32.00   0.00  140
 46  ω    -59.00  16.00   0.50    0.41    --  -38.82  54.00   0.00  150
 47  ω     26.00  74.00   0.50    0.41    --   38.82  32.00-180.00   96
 48  ω     46.00  98.00   0.50    0.41    --   38.82  54.00-180.00  104
 49  ω     27.00  85.00   0.50    0.41    --   38.82  65.00  90.00  116
 50  ω     48.00  73.00   0.50    0.41    --   38.82-138.00  30.00   50
 51  ω     68.00  94.00   0.50    1.63    --  100.00 -22.00-180.00   52
 52  ω     86.00 111.00   0.50    1.63    --  100.00  37.00 -60.00   50
 53  ω     99.00 137.00   0.50    1.63    --  100.00 111.00  60.00   76
 54  ω     84.00 117.00   0.50    1.63    --  100.00  93.00-150.00   66
 55  ω    120.00 145.00   0.50    1.63    --  100.00  93.00-150.00   50
 56  ω     44.00  73.00   0.50    1.63    --  100.00 -45.00-120.00   58
 57  ω     39.00  65.00   0.50    1.63    --  100.00 -22.00-180.00   52
 58  ω     82.00 139.00   0.50    1.63    --  100.00  69.00  60.00  114
 59  ω    104.00 130.00   0.50    1.63    --  100.00  37.00 -30.00   52
 60  ω     82.00 108.00   0.50    1.63    --  100.00-111.00-120.00   52
 61  ω     39.00  69.00   0.50    1.63    --  100.00-133.00  90.00   60
 62  ω     82.00 108.00   0.50    1.63    --  100.00-111.00 -30.00   52
 63  ω     39.00  64.00   0.50    1.63    --  100.00-133.00  60.00   50
 64  ω     91.00 117.00   0.50    1.63    --  100.00-133.00  60.00   52
 65  ω     63.00  89.00   0.50    1.63    --  100.00 -77.00-180.00   52
 66  ω    132.00 157.00   0.50    1.63    --  100.00  37.00 -60.00   50
 67  ω     46.00  72.00   0.50    1.63    --  100.00 -22.00  90.00   52
 68  ω     33.00  59.00   0.50    1.63    --  100.00-111.00-120.00   52
 69  ω     57.00 104.00   0.50    1.63    --  100.00-111.00 -60.00   94
 70  ω    131.00 156.00   0.50    1.63    --  100.00  61.00  30.00   50
 71  ω     92.00 117.00   0.50    1.63    --  100.00-133.00 150.00   50
 72  ω     50.00  83.00   0.50    1.63    --  100.00 -86.00  90.00   66
 73  ω    126.00 155.00   0.50    1.63    --  100.00  30.00   0.00   58
 74  ω    127.00 152.00   0.50    1.63    --  100.00  30.00 150.00   50
 75  ω     79.00 120.00   0.50    1.63    --  100.00 -69.00 -30.00   82
 76  ω     58.00  94.00   0.50    1.63    --  100.00 -37.00 -90.00   72
 77  ω     88.00 114.00   0.50    1.63    --  100.00 -86.00  90.00   52
 78  ω     30.00  73.00   0.50    1.63    --  100.00 -15.00-150.00   86
 79  ω    108.00 150.00   0.50    1.63    --  100.00   0.00 -90.00   84
 80  ω     99.00 125.00   0.50    1.63    --  100.00  30.00  60.00   52
 81  ω     90.00 155.00   0.50    1.63    --  100.00  45.00 120.00  130
 82  ω    125.00 151.00   0.50    1.63    --  100.00  77.00 -90.00   52
 83  ω     93.00 118.00   0.50    1.63    --  100.00  30.00   0.00   50
 84  ω     58.00 108.00   0.50    1.63    --  100.00-111.00  60.00  100
 85  ω     80.00 107.00   0.50    1.63    --  100.00-111.00 150.00   54
 86  ω     66.00  91.00   0.50    1.63    --  100.00 -93.00-150.00   50
 87  ω     59.00 116.00   0.50    1.63    --  100.00-133.00-120.00  114
 88  ω     49.00  75.00   0.50    1.63    --  100.00-133.00 -60.00   52
;
_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      -0.0627733000
_diffrn_orient_matrix_UB_12      0.0450233000
_diffrn_orient_matrix_UB_13      -0.0383297000
_diffrn_orient_matrix_UB_21      -0.0091202000
_diffrn_orient_matrix_UB_22      -0.0781519000
_diffrn_orient_matrix_UB_23      -0.0301376000
_diffrn_orient_matrix_UB_31      -0.0844961000
_diffrn_orient_matrix_UB_32      -0.0249531000
_diffrn_orient_matrix_UB_33      0.0251371000
_diffrn_oxdiff_ac3_digest_frames 
;
01951637aee7cc68ba2f7477df929e8e5c000314702
;
_diffrn_oxdiff_ac3_digest_hkl    
;
0163ac52addfa025579cc70738bb45d94cd6e0
;
_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                6050
_reflns_number_total             6461
_reflns_odcompleteness_completeness 98.49
_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 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_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         1.665
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.237
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         6461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.050
_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)+(0.0775P)²+14.5671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1154
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C4(H4A,H4B,H4C), C4B(H4BA,H4BB,H4BC), C7A(H7AA,H7AB,H7AC),
 C4A(H4AA,H4AB,H4AC), C5A(H5AA,H5AB,H5AC), C6A(H6AA,H6AB,H6AC), C6(H6A,H6B,H6C),
  C7B(H7BA,H7BB,H7BC), C5(H5A,H5B,H5C), C6B(H6BA,H6BB,H6BC), C5B(H5BA,H5BB,H5BC)
;
_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
I2 I 0.5000 0.48759(2) 0.7500 0.03134(13) Uani 1 2 d S T P . .
I1A I 0.78139(3) 0.67860(2) 0.84425(2) 0.03137(11) Uani 1 1 d . . . . .
I2A I 0.82533(2) 0.50899(2) 0.91750(2) 0.02894(11) Uani 1 1 d . . . . .
I1 I 0.47443(3) 0.32365(2) 0.66997(2) 0.03180(11) Uani 1 1 d . . . . .
I1B I 0.87583(2) 0.68044(2) 0.99519(2) 0.03279(12) Uani 1 1 d . . . . .
I3A I 1.0000 0.40478(3) 0.7500 0.03515(13) Uani 1 2 d S T P . .
I4A I 0.67995(3) 0.62567(2) 0.59167(2) 0.03519(12) Uani 1 1 d . . . . .
N2B N 0.9552(3) 0.8059(2) 1.12289(15) 0.0288(9) Uani 1 1 d . . . . .
N1B N 0.9305(3) 0.8711(2) 1.09512(15) 0.0298(9) Uani 1 1 d . . . . .
N2A N 0.7484(3) 0.8705(3) 0.74424(16) 0.0309(9) Uani 1 1 d . . . . .
N1 N 0.3974(3) 0.1954(2) 0.54308(15) 0.0279(8) Uani 1 1 d . . . . .
N2 N 0.4185(3) 0.1305(2) 0.57205(15) 0.0293(9) Uani 1 1 d . . . . .
N1A N 0.7552(3) 0.9142(2) 0.78482(16) 0.0304(9) Uani 1 1 d . . . . .
C1A C 0.7630(4) 0.7848(3) 0.80434(17) 0.0295(10) Uani 1 1 d . . . . .
C1B C 0.9117(4) 0.7608(3) 1.05094(17) 0.0289(10) Uani 1 1 d . . . . .
C7 C 0.4686(4) 0.0998(3) 0.6565(2) 0.0371(12) Uani 1 1 d . . . . .
H7A H 0.4163 0.0638 0.6598 0.056 Uiso 1 1 calc GR . . . .
H7B H 0.4822 0.1309 0.6860 0.056 Uiso 1 1 calc GR . . . .
H7C H 0.5222 0.0672 0.6504 0.056 Uiso 1 1 calc GR . . . .
C4 C 0.3984(4) 0.3472(3) 0.54849(18) 0.0338(11) Uani 1 1 d . . . . .
H4A H 0.3885 0.3440 0.5137 0.051 Uiso 1 1 calc GR . . . .
H4B H 0.4527 0.3805 0.5576 0.051 Uiso 1 1 calc GR . . . .
H4C H 0.3447 0.3719 0.5609 0.051 Uiso 1 1 calc GR . . . .
C3A C 0.7534(4) 0.7907(3) 0.75470(17) 0.0300(10) Uani 1 1 d . . . . .
C2 C 0.4126(4) 0.2640(3) 0.56859(18) 0.0298(10) Uani 1 1 d . . . . .
C3 C 0.4459(4) 0.1568(3) 0.61606(18) 0.0297(10) Uani 1 1 d . . . . .
C1 C 0.4439(4) 0.2411(3) 0.61476(18) 0.0280(10) Uani 1 1 d . . . . .
C2B C 0.9038(4) 0.8455(3) 1.05066(18) 0.0317(11) Uani 1 1 d . . . . .
C4B C 0.8769(4) 0.9027(3) 1.01137(18) 0.0355(11) Uani 1 1 d . . . . .
H4BA H 0.8207 0.9312 1.0178 0.053 Uiso 1 1 calc GR . . . .
H4BB H 0.8662 0.8726 0.9814 0.053 Uiso 1 1 calc GR . . . .
H4BC H 0.9262 0.9424 1.0089 0.053 Uiso 1 1 calc GR . . . .
C2A C 0.7646(4) 0.8634(3) 0.82252(18) 0.0333(11) Uani 1 1 d . . . . .
C7A C 0.7476(4) 0.7257(3) 0.71814(19) 0.0366(11) Uani 1 1 d . . . . .
H7AA H 0.7038 0.7417 0.6913 0.055 Uiso 1 1 calc GR . . . .
H7AB H 0.7270 0.6751 0.7321 0.055 Uiso 1 1 calc GR . . . .
H7AC H 0.8081 0.7173 0.7069 0.055 Uiso 1 1 calc GR . . . .
C4A C 0.7758(4) 0.8917(3) 0.87262(19) 0.0398(12) Uani 1 1 d . . . . .
H4AA H 0.8361 0.9171 0.8793 0.060 Uiso 1 1 calc GR . . . .
H4AB H 0.7708 0.8452 0.8940 0.060 Uiso 1 1 calc GR . . . .
H4AC H 0.7278 0.9314 0.8777 0.060 Uiso 1 1 calc GR . . . .
C5A C 0.7482(4) 1.0026(3) 0.7844(2) 0.0359(11) Uani 1 1 d . . . . .
H5AA H 0.7959 1.0253 0.7661 0.054 Uiso 1 1 calc GR . . . .
H5AB H 0.7565 1.0231 0.8171 0.054 Uiso 1 1 calc GR . . . .
H5AC H 0.6877 1.0187 0.7695 0.054 Uiso 1 1 calc GR . . . .
C6A C 0.7348(4) 0.9100(3) 0.69747(18) 0.0330(10) Uani 1 1 d . . . . .
H6AA H 0.6727 0.9328 0.6929 0.050 Uiso 1 1 calc GR . . . .
H6AB H 0.7426 0.8700 0.6725 0.050 Uiso 1 1 calc GR . . . .
H6AC H 0.7798 0.9537 0.6958 0.050 Uiso 1 1 calc GR . . . .
C6 C 0.4072(4) 0.0468(3) 0.5548(2) 0.0359(11) Uani 1 1 d . . . . .
H6A H 0.3426 0.0310 0.5544 0.054 Uiso 1 1 calc GR . . . .
H6B H 0.4449 0.0104 0.5761 0.054 Uiso 1 1 calc GR . . . .
H6C H 0.4264 0.0430 0.5226 0.054 Uiso 1 1 calc GR . . . .
C3B C 0.9452(4) 0.7380(3) 1.09653(18) 0.0290(10) Uani 1 1 d . . . . .
C7B C 0.9707(5) 0.6562(3) 1.1159(2) 0.0409(13) Uani 1 1 d . . . . .
H7BA H 1.0377 0.6509 1.1197 0.061 Uiso 1 1 calc GR . . . .
H7BB H 0.9446 0.6144 1.0938 0.061 Uiso 1 1 calc GR . . . .
H7BC H 0.9467 0.6492 1.1469 0.061 Uiso 1 1 calc GR . . . .
C5 C 0.3591(4) 0.1839(3) 0.49398(18) 0.0338(12) Uani 1 1 d . . . . .
H5A H 0.4029 0.1538 0.4765 0.051 Uiso 1 1 calc GR . . . .
H5B H 0.3471 0.2370 0.4789 0.051 Uiso 1 1 calc GR . . . .
H5C H 0.3017 0.1533 0.4935 0.051 Uiso 1 1 calc GR . . . .
C6B C 0.9902(5) 0.8147(3) 1.17320(19) 0.0365(12) Uani 1 1 d . . . . .
H6BA H 1.0448 0.8495 1.1757 0.055 Uiso 1 1 calc GR . . . .
H6BB H 1.0064 0.7611 1.1866 0.055 Uiso 1 1 calc GR . . . .
H6BC H 0.9429 0.8394 1.1909 0.055 Uiso 1 1 calc GR . . . .
C5B C 0.9387(4) 0.9547(3) 1.11346(18) 0.0323(11) Uani 1 1 d . . . . .
H5BA H 0.9211 0.9561 1.1461 0.048 Uiso 1 1 calc GR . . . .
H5BB H 0.8982 0.9905 1.0932 0.048 Uiso 1 1 calc GR . . . .
H5BC H 1.0023 0.9731 1.1133 0.048 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
I2 I1 3.5153(4) . ?
I1A I2A 3.4962(4) . ?
I1A C1A 2.083(5) . ?
I2A I1B 3.6060(4) . ?
I1 C1 2.083(5) . ?
I1B C1B 2.084(5) . ?
N2B N1B 1.357(6) . ?
N2B C3B 1.342(6) . ?
N2B C6B 1.469(7) . ?
N1B C2B 1.345(7) . ?
N1B C5B 1.471(6) . ?
N2A N1A 1.348(6) . ?
N2A C3A 1.346(7) . ?
N2A C6A 1.468(6) . ?
N1 N2 1.363(6) . ?
N1 C2 1.345(6) . ?
N1 C5 1.456(6) . ?
N2 C3 1.340(7) . ?
N2 C6 1.465(6) . ?
N1A C2A 1.350(7) . ?
N1A C5A 1.459(6) . ?
C1A C3A 1.397(7) . ?
C1A C2A 1.390(7) . ?
C1B C2B 1.398(7) . ?
C1B C3B 1.384(7) . ?
C7 C3 1.490(7) . ?
C4 C2 1.489(6) . ?
C3A C7A 1.483(7) . ?
C2 C1 1.391(7) . ?
C3 C1 1.389(7) . ?
C2B C4B 1.480(7) . ?
C2A C4A 1.482(7) . ?
C3B C7B 1.488(7) . ?

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
C1A I1A I2A 175.31(14) . . ?
I1A I2A I1B 75.518(11) . . ?
C1 I1 I2 169.44(14) . . ?
C1B I1B I2A 167.92(14) . . ?
N1B N2B C6B 121.9(4) . . ?
C3B N2B N1B 109.2(4) . . ?
C3B N2B C6B 128.8(4) . . ?
N2B N1B C5B 121.9(4) . . ?
C2B N1B N2B 109.2(4) . . ?
C2B N1B C5B 128.9(4) . . ?
N1A N2A C6A 121.3(4) . . ?
C3A N2A N1A 109.7(4) . . ?
C3A N2A C6A 129.0(4) . . ?
N2 N1 C5 120.9(4) . . ?
C2 N1 N2 108.7(4) . . ?
C2 N1 C5 130.3(4) . . ?
N1 N2 C6 121.8(4) . . ?
C3 N2 N1 109.4(4) . . ?
C3 N2 C6 128.7(4) . . ?
N2A N1A C2A 109.4(4) . . ?
N2A N1A C5A 121.7(4) . . ?
C2A N1A C5A 128.8(5) . . ?
C3A C1A I1A 126.5(4) . . ?
C2A C1A I1A 125.8(4) . . ?
C2A C1A C3A 107.6(4) . . ?
C2B C1B I1B 127.9(4) . . ?
C3B C1B I1B 124.8(4) . . ?
C3B C1B C2B 107.3(4) . . ?
N2A C3A C1A 106.6(4) . . ?
N2A C3A C7A 123.6(5) . . ?
C1A C3A C7A 129.8(5) . . ?
N1 C2 C4 123.9(4) . . ?
N1 C2 C1 107.2(4) . . ?
C1 C2 C4 128.9(4) . . ?
N2 C3 C7 122.1(4) . . ?
N2 C3 C1 107.1(4) . . ?
C1 C3 C7 130.7(5) . . ?
C2 C1 I1 123.5(3) . . ?
C3 C1 I1 129.0(4) . . ?
C3 C1 C2 107.4(4) . . ?
N1B C2B C1B 106.9(4) . . ?
N1B C2B C4B 122.1(5) . . ?
C1B C2B C4B 130.9(5) . . ?
N1A C2A C1A 106.8(4) . . ?
N1A C2A C4A 123.4(5) . . ?
C1A C2A C4A 129.8(5) . . ?
N2B C3B C1B 107.5(4) . . ?
N2B C3B C7B 122.7(5) . . ?
C1B C3B C7B 129.8(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 2.740
_oxdiff_exptl_absorpt_empirical_full_min 0.410
