# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_jfr659
_database_code_depnum_ccdc_archive 'CCDC 2246522'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite Claude Bernard Lyon
France
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_audit_creation_date             2022-12-14
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 I N O2'
_chemical_formula_sum            'C16 H22 I N O2'
_chemical_formula_weight         387.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H22 I1 N1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6026(3)
_cell_length_b                   10.9032(3)
_cell_length_c                   15.9038(5)
_cell_angle_alpha                80.907(3)
_cell_angle_beta                 89.846(2)
_cell_angle_gamma                80.988(2)
_cell_volume                     1623.48(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25455
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1770
_cell_measurement_theta_min      5.4000
_shelx_estimated_absorpt_T_max   0.860
_shelx_estimated_absorpt_T_min   0.052
_exptl_absorpt_coefficient_mu    15.506
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.040
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.74a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 10 0.0094
0 -3 -10 0.0134
-6 0 0 0.2358
6 0 0 0.2296
0 5 -5 0.0136
0 -5 5 0.0010

_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0515 3.4996 9.6520 -0.4392 0.3324 0.8346
-0.0515 -3.4996 -9.6520 0.4392 -0.3324 -0.8346
-6.1506 0.0250 -0.0337 -0.6824 0.5243 -0.5094
6.1500 -0.0308 0.0174 0.6831 -0.5248 0.5080
0.1141 5.2661 -5.4958 0.5916 0.7719 -0.2327
-0.1141 -5.2661 5.4958 -0.5916 -0.7719 0.2327

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47510
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.996
_diffrn_reflns_theta_min         5.385
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  34.00   0.50    0.50    --  -43.82  54.00  84.00  150
  2  ω    -33.00  41.00   0.50    0.50    --   44.69 -54.00 -59.00  148
  3  ω   -165.00 -83.00   0.50    2.50    --  -87.52 -54.00 -59.00  164
  4  ω    -41.00 -10.00   0.50    2.50    --  -87.52  54.00  84.00   62
  5  ω    105.00 178.00   0.50    2.50    --  111.23  54.00  84.00  146
  6  ω    -21.00  10.00   0.50    0.50    --   10.00  90.00 -63.98   62
  7  ω    -25.00   2.00   0.50    0.50    --   14.00 102.00 163.15   54
  8  ω     -5.00  21.00   0.50    0.50    --   18.00  77.00-150.84   52
  9  ω     -5.00  22.00   0.50    0.50    --   18.00  76.00 -40.21   54
 10  ω     -5.00  21.00   0.50    0.50    --   18.00  77.00 175.63   52
 11  ω     -6.00  20.00   0.50    0.50    --   18.00  78.00  77.68   52
 12  ω      3.00  33.00   0.50    0.50    --   22.00  68.00-177.91   60
 13  ω     12.00  38.00   0.50    0.50    --   30.00  67.00-101.68   52
 14  ω     16.00  43.00   0.50    0.50    --   34.00  65.00  -8.71   54
 15  ω     21.00  47.00   0.50    0.50    --   38.00  63.00 -29.80   52
 16  ω     26.00  57.00   0.50    0.50    --   42.00  60.00 106.45   62
 17  ω    -19.00  37.00   0.50    0.50    --  -43.82  38.00-150.00  112
 18  ω     28.00  54.00   0.50    0.50    --   44.69  61.00 -42.61   52
 19  ω   -124.00 -31.00   0.50    0.50    --  -46.00 -52.00  33.49  186
 20  ω   -157.00-102.00   0.50    2.50    --  -87.52 -77.00  60.00  110
 21  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00 -30.00  186
 22  ω   -157.00-102.00   0.50    2.50    --  -87.52 -77.00-150.00  110
 23  ω   -157.00-102.00   0.50    2.50    --  -87.52 -77.00 -90.00  110
 24  ω    -51.00 -12.00   0.50    2.50    --  -87.52  61.00-180.00   78
 25  ω    -51.00 -12.00   0.50    2.50    --  -87.52  61.00 -90.00   78
 26  ω     29.00  92.00   0.50    2.50    --  101.51 -95.00  60.00  126
 27  ω    124.00 171.00   0.50    2.50    --  101.51  77.00 -30.00   94
 28  ω    112.00 176.00   0.50    2.50    --  101.51 125.00 150.00  128
 29  ω     34.00 101.00   0.50    2.50    --  101.51-125.00-180.00  134
 30  ω    109.00 177.00   0.50    2.50    --  101.51  61.00 -60.00  136
 31  ω    124.00 171.00   0.50    2.50    --  101.51  77.00-120.00   94
 32  ω     34.00 101.00   0.50    2.50    --  101.51-125.00 -90.00  134
 33  ω     29.00  92.00   0.50    2.50    --  101.51 -95.00   0.00  126
 34  ω    109.00 177.00   0.50    2.50    --  101.51  61.00  30.00  136
 35  ω     29.00  92.00   0.50    2.50    --  101.51 -95.00 -90.00  126
 36  ω    105.00 178.00   0.50    2.50    --  101.51  54.00  84.00  146
 37  ω    109.00 178.00   0.50    2.50    --  111.23  61.00 150.00  138
 38  ω     39.00  92.00   0.50    2.50    --  111.23 -95.00 -30.00  106
 39  ω     39.00  92.00   0.50    2.50    --  111.23 -95.00-180.00  106
 40  ω     39.00  92.00   0.50    2.50    --  111.23 -95.00-120.00  106
 41  ω     39.00  92.00   0.50    2.50    --  111.23 -95.00 -60.00  106
 42  ω     39.00  92.00   0.50    2.50    --  111.23 -95.00 150.00  106
 43  ω     39.00  92.00   0.50    2.50    --  111.23 -95.00-150.00  106
 44  ω     39.00  92.00   0.50    2.50    --  111.23 -95.00  30.00  106
 45  ω     42.00  75.00   0.50    2.50    --  111.23 -77.00  90.00   66
 46  ω    109.00 178.00   0.50    2.50    --  111.23  61.00  60.00  138
 47  ω     39.00  92.00   0.50    2.50    --  111.23 -95.00  90.00  106
 48  ω     17.00  44.00   0.50    0.50    --   34.00  64.00 142.74   54
 49  ω     28.00  57.00   0.50    0.50    --   44.69  60.00  13.98   58
 50  ω     28.00  57.00   0.50    0.50    --   44.69  60.00  45.22   58
 51  ω     29.00  59.00   0.50    0.50    --   44.69  59.00-177.32   60
 52  ω     30.00  60.00   0.50    0.50    --   44.69  55.00-131.60   60
 53  ω     29.00  59.00   0.50    0.50    --   44.69  59.00 160.16   60
 54  ω     28.00  57.00   0.50    0.50    --   44.69  60.00 -96.58   58
 55  ω     29.00  59.00   0.50    0.50    --   44.69  59.00-153.28   60
 56  ω     30.00  57.00   0.50    0.50    --   46.00  60.00  76.24   54
 57  ω     60.00 153.00   0.50    0.50    --   74.00  50.00 -94.92  186
 58  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00-120.00  186
 59  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00  60.00  186
 60  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00 120.00  186
 61  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00 -90.00  186
 62  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00-150.00  186
 63  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00  30.00  186
 64  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00   0.00  186
 65  ω    -74.00 -13.00   0.50    2.50    --  -87.52 125.00   0.00  122
 66  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00 150.00  186
 67  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00  90.00  186
 68  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00-180.00  186
 69  ω    -67.00 -18.00   0.50    2.50    --  -87.52  77.00  30.00   98
 70  ω    -74.00 -13.00   0.50    2.50    --  -87.52 125.00-180.00  122
 71  ω   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00 -60.00  186
 72  ω   -173.00 -80.00   0.50    2.50    --  -94.50 -48.00 142.02  186
 73  ω   -172.00 -80.00   0.50    2.50    --  -94.50 -52.00 177.21  184
 74  ω   -173.00 -80.00   0.50    2.50    --  -94.50 -51.00 117.14  186
 75  ω   -173.00 -80.00   0.50    2.50    --  -94.50 -51.00 -40.77  186
 76  ω   -172.00 -83.00   0.50    2.50    --  -94.50 -55.00  61.89  178
 77  ω   -173.00 -80.00   0.50    2.50    --  -94.50 -49.00-120.56  186
 78  ω   -172.00 -80.00   0.50    2.50    --  -94.50 -52.00  68.19  184
 79  ω     88.00 178.00   0.50    2.50    --  101.51  45.00 -30.00  180
 80  ω     88.00 178.00   0.50    2.50    --  101.51  45.00  30.00  180
 81  ω     52.00 136.00   0.50    2.50    --  101.51  15.00-150.00  168
 82  ω     88.00 178.00   0.50    2.50    --  101.51  45.00  60.00  180
 83  ω     88.00 178.00   0.50    2.50    --  101.51  45.00-120.00  180
 84  ω     88.00 178.00   0.50    2.50    --  101.51  45.00 -60.00  180
 85  ω    124.00 171.00   0.50    2.50    --  101.51  77.00-150.00   94
 86  ω     85.00 166.00   0.50    2.50    --  101.51  30.00 -60.00  162
 87  ω     62.00 136.00   0.50    2.50    --  111.23  15.00 -90.00  148
 88  ω     -5.00  22.00   0.50    0.50    --   18.00  76.00 133.25   54
 89  ω     12.00  38.00   0.50    0.50    --   30.00  67.00  67.83   52
 90  ω     17.00  44.00   0.50    0.50    --   34.00  64.00 -53.19   54
 91  ω     21.00  47.00   0.50    0.50    --   38.00  63.00-127.34   52
 92  ω    -66.00  21.00   0.50    0.50    --  -43.82  77.00 -30.00  174
 93  ω    -19.00  37.00   0.50    0.50    --  -43.82  38.00  30.00  112
 94  ω    -19.00  37.00   0.50    0.50    --  -43.82  38.00 150.00  112
 95  ω     28.00  57.00   0.50    0.50    --   44.69  60.00 141.57   58
 96  ω     30.00  57.00   0.50    0.50    --   46.00  60.00  -7.54   54
 97  ω     34.00  60.00   0.50    0.50    --   50.00  57.00 -32.60   52
 98  ω   -172.00 -80.00   0.50    2.50    --  -94.50 -52.00-165.44  184
 99  ω   -169.00 -92.00   0.50    2.50    --  -94.50 -63.00 117.51  154
100  ω   -173.00 -80.00   0.50    2.50    --  -94.50 -49.00 148.04  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1114665000
_diffrn_orient_matrix_UB_12      0.0448457000
_diffrn_orient_matrix_UB_13      -0.0623594000
_diffrn_orient_matrix_UB_21      -0.0846228000
_diffrn_orient_matrix_UB_22      0.1340900000
_diffrn_orient_matrix_UB_23      -0.0137269000
_diffrn_orient_matrix_UB_31      0.0825434000
_diffrn_orient_matrix_UB_32      0.0317780000
_diffrn_orient_matrix_UB_33      0.0745088000
_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'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5557
_reflns_number_total             6462
_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 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         2.091
_refine_diff_density_min         -1.391
_refine_diff_density_rms         0.162
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.040
_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)+(0.0853P)²+8.0133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1555
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C26(H26), C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B),
 C15(H15A,H15B), C23(H23A,H23B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B),
  C30(H30A,H30B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), N2(H2A), C18(H18), C19(H19), C21(H21),
  C22(H22)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C)
;
_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 0.98267(4) 0.83286(4) 1.10744(2) 0.03590(14) Uani 1 1 d . . . . .
O1 O 0.5893(4) 0.4626(4) 0.7208(3) 0.0366(10) Uani 1 1 d . . . . .
O2 O 0.8731(6) 0.0910(5) 0.7432(3) 0.0469(12) Uani 1 1 d . . . . .
N1 N 0.7731(5) 0.5364(5) 0.7712(4) 0.0345(12) Uani 1 1 d . . . . .
H1 H 0.863143 0.530289 0.776262 0.041 Uiso 1 1 calc R U . . .
C1 C 0.8894(6) 0.7656(6) 1.0072(4) 0.0305(12) Uani 1 1 d . . . . .
C2 C 0.8816(6) 0.6393(6) 1.0151(4) 0.0340(13) Uani 1 1 d . . . . .
H2 H 0.919420 0.583965 1.063066 0.041 Uiso 1 1 calc R U . . .
C3 C 0.8170(7) 0.5960(6) 0.9509(4) 0.0358(14) Uani 1 1 d . . . . .
H3 H 0.811933 0.510691 0.956018 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7591(6) 0.6767(7) 0.8784(4) 0.0377(15) Uani 1 1 d . . . . .
C5 C 0.7691(7) 0.8035(7) 0.8723(5) 0.0385(14) Uani 1 1 d . . . . .
H5 H 0.731842 0.859202 0.824384 0.046 Uiso 1 1 calc R U . . .
C6 C 0.8341(7) 0.8490(6) 0.9370(4) 0.0353(14) Uani 1 1 d . . . . .
H6 H 0.839758 0.934122 0.932564 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6828(7) 0.6267(8) 0.8119(5) 0.0451(17) Uani 1 1 d . . . . .
H7A H 0.606114 0.587526 0.838326 0.054 Uiso 1 1 calc R U . . .
H7B H 0.642010 0.696323 0.768919 0.054 Uiso 1 1 calc R U . . .
C8 C 0.7178(6) 0.4613(6) 0.7254(4) 0.0316(12) Uani 1 1 d . . . . .
C9 C 0.8213(7) 0.3825(6) 0.6762(4) 0.0359(14) Uani 1 1 d . . . . .
H9A H 0.906016 0.350566 0.710935 0.043 Uiso 1 1 calc R U . . .
H9B H 0.847595 0.435147 0.625482 0.043 Uiso 1 1 calc R U . . .
C10 C 0.7614(7) 0.2718(7) 0.6500(4) 0.0381(14) Uani 1 1 d . . . . .
H10 H 0.672376 0.301712 0.617858 0.046 Uiso 1 1 calc R U . . .
C11 C 0.7406(7) 0.1728(6) 0.7261(5) 0.0406(15) Uani 1 1 d . . . . .
H11A H 0.712373 0.212462 0.775222 0.049 Uiso 1 1 calc R U . . .
H11B H 0.668040 0.125524 0.713087 0.049 Uiso 1 1 calc R U . . .
C12 C 0.9575(9) 0.1045(7) 0.6676(5) 0.0476(17) Uani 1 1 d . . . . .
H12A H 0.988149 0.023129 0.650626 0.057 Uiso 1 1 calc R U . . .
H12B H 1.040294 0.140853 0.678645 0.057 Uiso 1 1 calc R U . . .
C13 C 0.8661(7) 0.1899(6) 0.5984(4) 0.0390(14) Uani 1 1 d . . . . .
H13 H 0.811882 0.137656 0.570774 0.047 Uiso 1 1 calc R U . . .
C14 C 0.9486(8) 0.2591(7) 0.5301(5) 0.0406(15) Uani 1 1 d . . . . .
H14A H 1.009576 0.305234 0.557017 0.049 Uiso 1 1 calc R U . . .
H14B H 0.883045 0.319757 0.492358 0.049 Uiso 1 1 calc R U . . .
C15 C 1.0387(8) 0.1724(7) 0.4771(5) 0.0444(16) Uani 1 1 d . . . . .
H15A H 1.108227 0.115259 0.514413 0.053 Uiso 1 1 calc R U . . .
H15B H 0.978617 0.122282 0.453305 0.053 Uiso 1 1 calc R U . . .
C16 C 1.1144(8) 0.2416(8) 0.4051(5) 0.0478(17) Uani 1 1 d . . . . .
H16A H 1.048695 0.277262 0.359048 0.072 Uiso 1 1 calc R U . . .
H16B H 1.188506 0.183730 0.385462 0.072 Uiso 1 1 calc R U . . .
H16C H 1.154008 0.307463 0.425203 0.072 Uiso 1 1 calc R U . . .
I2 I 0.60986(4) 0.18631(4) 0.38936(2) 0.03581(14) Uani 1 1 d . . . . .
O3 O 0.0769(4) 0.5306(5) 0.7839(3) 0.0368(10) Uani 1 1 d . . . . .
O4 O 0.2351(5) 0.8963(4) 0.7584(3) 0.0392(10) Uani 1 1 d . . . . .
N2 N 0.2859(5) 0.4590(5) 0.7322(3) 0.0339(11) Uani 1 1 d . . . . .
H2A H 0.373121 0.467160 0.725720 0.041 Uiso 1 1 calc R U . . .
C17 C 0.4855(7) 0.2465(6) 0.4889(4) 0.0327(13) Uani 1 1 d . . . . .
C18 C 0.4611(7) 0.1581(6) 0.5592(4) 0.0389(14) Uani 1 1 d . . . . .
H18 H 0.500396 0.073861 0.562304 0.047 Uiso 1 1 calc R U . . .
C19 C 0.3777(8) 0.1976(7) 0.6237(4) 0.0411(15) Uani 1 1 d . . . . .
H19 H 0.360312 0.138988 0.670140 0.049 Uiso 1 1 calc R U . . .
C20 C 0.3194(6) 0.3233(7) 0.6207(4) 0.0362(14) Uani 1 1 d . . . . .
C21 C 0.3463(7) 0.4088(6) 0.5507(4) 0.0357(13) Uani 1 1 d . . . . .
H21 H 0.308710 0.493295 0.547976 0.043 Uiso 1 1 calc R U . . .
C22 C 0.4287(6) 0.3706(6) 0.4841(4) 0.0342(13) Uani 1 1 d . . . . .
H22 H 0.444773 0.428851 0.437086 0.041 Uiso 1 1 calc R U . . .
C23 C 0.2273(7) 0.3661(8) 0.6905(5) 0.0451(17) Uani 1 1 d . . . . .
H23A H 0.134450 0.403169 0.666793 0.054 Uiso 1 1 calc R U . . .
H23B H 0.216706 0.293823 0.732736 0.054 Uiso 1 1 calc R U . . .
C24 C 0.2063(6) 0.5292(6) 0.7792(4) 0.0280(12) Uani 1 1 d . . . . .
C25 C 0.2815(6) 0.6098(6) 0.8288(4) 0.0290(12) Uani 1 1 d . . . . .
H25A H 0.326090 0.557278 0.879489 0.035 Uiso 1 1 calc R U . . .
H25B H 0.355161 0.641399 0.793918 0.035 Uiso 1 1 calc R U . . .
C26 C 0.1839(6) 0.7200(6) 0.8548(4) 0.0326(13) Uani 1 1 d . . . . .
H26 H 0.105883 0.690099 0.887655 0.039 Uiso 1 1 calc R U . . .
C27 C 0.1262(7) 0.8193(6) 0.7789(4) 0.0365(14) Uani 1 1 d . . . . .
H27A H 0.106157 0.779686 0.730759 0.044 Uiso 1 1 calc R U . . .
H27B H 0.040068 0.869956 0.793686 0.044 Uiso 1 1 calc R U . . .
C28 C 0.3219(7) 0.8882(6) 0.8329(4) 0.0371(14) Uani 1 1 d . . . . .
H28A H 0.321852 0.971095 0.847786 0.044 Uiso 1 1 calc R U . . .
H28B H 0.418248 0.852067 0.822897 0.044 Uiso 1 1 calc R U . . .
C29 C 0.2587(6) 0.8030(6) 0.9055(4) 0.0338(13) Uani 1 1 d . . . . .
H29 H 0.185351 0.856612 0.931832 0.041 Uiso 1 1 calc R U . . .
C30 C 0.3647(7) 0.7367(6) 0.9750(4) 0.0344(13) Uani 1 1 d . . . . .
H30A H 0.441951 0.687680 0.949636 0.041 Uiso 1 1 calc R U . . .
H30B H 0.319603 0.678824 1.014658 0.041 Uiso 1 1 calc R U . . .
C31 C 0.4243(8) 0.8281(7) 1.0243(5) 0.0417(15) Uani 1 1 d . . . . .
H31A H 0.473052 0.883672 0.985224 0.050 Uiso 1 1 calc R U . . .
H31B H 0.346926 0.879501 1.047889 0.050 Uiso 1 1 calc R U . . .
C32 C 0.5252(7) 0.7606(8) 1.0957(5) 0.0467(17) Uani 1 1 d . . . . .
H32A H 0.602262 0.709928 1.072736 0.070 Uiso 1 1 calc R U . . .
H32B H 0.476529 0.707779 1.135752 0.070 Uiso 1 1 calc R U . . .
H32C H 0.560667 0.821250 1.124030 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.113(6) . ?
O1 C8 1.234(7) . ?
O2 C11 1.434(8) . ?
O2 C12 1.449(9) . ?
N1 C7 1.439(8) . ?
N1 C8 1.345(8) . ?
C1 C2 1.377(9) . ?
C1 C6 1.373(9) . ?
C2 C3 1.377(9) . ?
C3 C4 1.393(10) . ?
C4 C5 1.389(10) . ?
C4 C7 1.506(9) . ?
C5 C6 1.398(10) . ?
C8 C9 1.510(9) . ?
C9 C10 1.530(9) . ?
C10 C11 1.524(10) . ?
C10 C13 1.558(9) . ?
C12 C13 1.509(10) . ?
C13 C14 1.516(10) . ?
C14 C15 1.531(9) . ?
C15 C16 1.518(10) . ?
I2 C17 2.107(6) . ?
O3 C24 1.243(7) . ?
O4 C27 1.446(8) . ?
O4 C28 1.434(8) . ?
N2 C23 1.475(8) . ?
N2 C24 1.314(8) . ?
C17 C18 1.400(9) . ?
C17 C22 1.368(9) . ?
C18 C19 1.381(10) . ?
C19 C20 1.390(10) . ?
C20 C21 1.386(10) . ?
C20 C23 1.505(9) . ?
C21 C22 1.397(9) . ?
C24 C25 1.528(8) . ?
C25 C26 1.515(8) . ?
C26 C27 1.530(9) . ?
C26 C29 1.556(9) . ?
C28 C29 1.548(9) . ?
C29 C30 1.519(9) . ?
C30 C31 1.538(9) . ?
C31 C32 1.512(11) . ?

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
C11 O2 C12 108.5(5) . . ?
C8 N1 C7 120.5(5) . . ?
C2 C1 I1 119.0(5) . . ?
C6 C1 I1 119.5(5) . . ?
C6 C1 C2 121.5(6) . . ?
C1 C2 C3 119.0(6) . . ?
C2 C3 C4 121.8(6) . . ?
C3 C4 C7 120.0(7) . . ?
C5 C4 C3 117.8(6) . . ?
C5 C4 C7 122.1(7) . . ?
C4 C5 C6 121.2(6) . . ?
C1 C6 C5 118.8(6) . . ?
N1 C7 C4 112.9(5) . . ?
O1 C8 N1 121.4(6) . . ?
O1 C8 C9 122.6(6) . . ?
N1 C8 C9 116.0(5) . . ?
C8 C9 C10 112.6(5) . . ?
C9 C10 C13 113.4(5) . . ?
C11 C10 C9 112.4(6) . . ?
C11 C10 C13 99.7(5) . . ?
O2 C11 C10 107.0(5) . . ?
O2 C12 C13 107.2(6) . . ?
C12 C13 C10 102.4(6) . . ?
C12 C13 C14 113.8(6) . . ?
C14 C13 C10 117.0(6) . . ?
C13 C14 C15 113.6(6) . . ?
C16 C15 C14 114.0(6) . . ?
C28 O4 C27 108.9(5) . . ?
C24 N2 C23 120.6(5) . . ?
C18 C17 I2 119.3(5) . . ?
C22 C17 I2 119.9(5) . . ?
C22 C17 C18 120.8(6) . . ?
C19 C18 C17 119.1(6) . . ?
C18 C19 C20 121.3(6) . . ?
C19 C20 C23 121.3(6) . . ?
C21 C20 C19 118.3(6) . . ?
C21 C20 C23 120.4(6) . . ?
C20 C21 C22 121.4(6) . . ?
C17 C22 C21 119.1(6) . . ?
N2 C23 C20 112.2(5) . . ?
O3 C24 N2 122.4(5) . . ?
O3 C24 C25 121.3(5) . . ?
N2 C24 C25 116.3(5) . . ?
C26 C25 C24 113.4(5) . . ?
C25 C26 C27 112.9(5) . . ?
C25 C26 C29 114.1(5) . . ?
C27 C26 C29 99.3(5) . . ?
O4 C27 C26 105.9(5) . . ?
O4 C28 C29 106.8(5) . . ?
C28 C29 C26 101.8(5) . . ?
C30 C29 C26 117.8(5) . . ?
C30 C29 C28 114.0(5) . . ?
C29 C30 C31 113.0(6) . . ?
C32 C31 C30 112.4(6) . . ?

_olex2_submission_original_sample_id JFR659
_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 2.800
_oxdiff_exptl_absorpt_empirical_full_min 0.423

# start Validation Reply Form
_vrf_PLAT431_jfr659              
;
PROBLEM: Short Inter HL..A Contact  I2       ..O4       .       2.96 Ang.  
RESPONSE: There is no hydrogen atom on the oxygen. The short Iodine to oxygen atomic distance
is characteristic of an intermolecular halogen interactions.
;

