# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_isk-466-01-298k_autored
_database_code_depnum_ccdc_archive 'CCDC 2525256'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Seki'
;Shizuoka University
Japan
;
_audit_update_record             
;
2026-04-15 deposited with the CCDC.	2026-04-16 downloaded from the CCDC.
;
_audit_creation_date             2026-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.04.07 svn.r39635298 for OlexSys, GUI svn.r7533)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 I N O2'
_chemical_formula_sum            'C17 H14 I N O2'
_chemical_formula_weight         391.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H14INO2
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.1022(4)
_cell_length_b                   7.1059(2)
_cell_length_c                   27.7748(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3178.01(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4337
_cell_measurement_temperature    298.03(18)
_cell_measurement_theta_max      76.0780
_cell_measurement_theta_min      3.1630
_shelx_estimated_absorpt_T_max   0.742
_shelx_estimated_absorpt_T_min   0.059
_exptl_absorpt_coefficient_mu    15.864
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.051
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 0 12 0.0293
-8 0 -12 0.0239
-1 5 1 0.2266
1 -5 -1 0.2187
-8 0 12 0.0223
7 0 -13 0.0274
7 0 13 0.0207
-7 0 -13 0.0169
-7 0 13 0.0223

_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
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
7.6988 0.1331 12.1869 -0.1162 -0.3404 0.9331
-7.7065 -0.0945 -12.1779 0.1188 0.3478 -0.9300
-0.6621 4.5904 1.4760 0.3070 0.8663 0.3941
0.8712 -4.5897 -1.1466 -0.3103 -0.8761 -0.3690
-7.8023 -0.1574 11.9583 -0.9013 0.4280 -0.0674
7.2966 0.0203 -12.8900 0.9031 -0.4292 -0.0093
7.3826 -0.1069 12.7609 -0.1769 -0.3648 0.9141
-7.3832 0.0682 -12.7639 0.1736 0.3578 -0.9175
-7.2966 -0.0203 12.8900 -0.9031 0.4292 0.0093

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10521
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_min         3.182
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.03(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -62.00   0.50    2.02    --  -47.55 -66.00 -72.00  114
  2  ω    -76.00 -50.00   0.50    8.07    -- -104.50  66.00-159.00   52
  3  ω    -73.00 -45.00   0.50    8.07    -- -104.50  66.00  62.00   56
  4  ω    -97.00 -38.00   0.50    8.07    -- -104.50  93.00 -59.00  118
  5  ω     89.00 167.00   0.50    8.07    --  107.14  66.00-159.00  156
  6  ω    -20.00  27.00   0.50    2.02    --  -47.55  19.00  90.00   94
  7  ω    -23.00  27.00   0.50    2.02    --  -47.55  19.00-150.00  100
  8  ω    -16.00  10.00   0.50    2.02    --  -47.55  19.00-180.00   52
  9  ω    -10.00  25.00   0.50    2.02    --   47.55 -19.00 -90.00   70
 10  ω   -104.00 -37.00   0.50    8.07    -- -104.50 125.00-150.00  134
 11  ω    -62.00 -36.00   0.50    8.07    -- -104.50  57.00-180.00   52
 12  ω     43.00  69.00   0.50    8.07    --  107.14 -57.00-120.00   52
 13  ω     40.00  67.00   0.50    8.07    --  107.14 -57.00 120.00   54
 14  ω     36.00  69.00   0.50    8.07    --  107.14 -57.00-150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0496215000
_diffrn_orient_matrix_UB_12      0.0874809000
_diffrn_orient_matrix_UB_13      -0.0418390000
_diffrn_orient_matrix_UB_21      -0.0529949000
_diffrn_orient_matrix_UB_22      0.1799239000
_diffrn_orient_matrix_UB_23      0.0035836000
_diffrn_orient_matrix_UB_31      0.0624505000
_diffrn_orient_matrix_UB_32      0.0832171000
_diffrn_orient_matrix_UB_33      0.0362038000
_diffrn_oxdiff_digest_hkl        
;
011566fa11fe018d2d4595254f148375a53ff9
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2390
_reflns_number_total             2895
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.800
_refine_diff_density_min         -1.151
_refine_diff_density_rms         0.186
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2895
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.069
_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)+(0.1219P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1789
_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. Restrained distances
 C00I-C00L
 1.39 with sigma of 0.02
 C00J-C00E
 1.39 with sigma of 0.02
 C00L-C00K
 1.39 with sigma of 0.02
 C00K-C00J
 1.39 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C00E \\sim C00F \\sim C00I \\sim C00J \\sim C00L \\sim C00K: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00C(H00C), C00E(H00F), C00I(H00J), C00J(H00K),
 C00K(H00L), C00L(H00M)
4.b Idealised Me refined as rotating group:
 C00D(H00B,H00D,H00E), C00G(H00G,H00H,H00I)
;
_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
I001 I 0.46359(2) 0.59558(6) 0.20980(2) 0.0520(2) Uani 1 1 d . . . . .
O002 O 0.4195(3) 0.5800(7) 0.40302(16) 0.0621(13) Uani 1 1 d . . . . .
O003 O 0.2716(3) 0.5746(8) 0.22362(17) 0.0625(14) Uani 1 1 d . . . . .
N004 N 0.1584(3) 0.5707(7) 0.39068(17) 0.0477(11) Uani 1 1 d . . . . .
C005 C 0.3903(4) 0.5853(8) 0.2722(2) 0.0440(13) Uani 1 1 d . . . . .
C006 C 0.3833(4) 0.5738(8) 0.3584(2) 0.0451(13) Uani 1 1 d . . . . .
C007 C 0.4287(4) 0.5858(8) 0.3166(2) 0.0471(14) Uani 1 1 d . . . . .
H007 H 0.486244 0.594487 0.318335 0.057 Uiso 1 1 calc R U . . .
C008 C 0.2958(4) 0.5549(8) 0.3564(2) 0.0416(12) Uani 1 1 d . . . . .
C009 C 0.2422(4) 0.5341(9) 0.39977(19) 0.0461(13) Uani 1 1 d . . . . .
C00A C 0.2593(4) 0.5574(9) 0.3109(2) 0.0455(13) Uani 1 1 d . . . . .
H00A H 0.201761 0.549143 0.308800 0.055 Uiso 1 1 calc R U . . .
C00B C 0.3049(4) 0.5715(8) 0.2686(2) 0.0439(12) Uani 1 1 d . . . . .
C00C C 0.2656(4) 0.4839(10) 0.4443(2) 0.0506(14) Uani 1 1 d . . . . .
H00C H 0.322088 0.459610 0.447652 0.061 Uiso 1 1 calc R U . . .
C00D C 0.1838(5) 0.5802(11) 0.2191(3) 0.0587(18) Uani 1 1 d . . . . .
H00B H 0.169168 0.600825 0.185965 0.088 Uiso 1 1 calc R U . . .
H00D H 0.162045 0.680674 0.238419 0.088 Uiso 1 1 calc R U . . .
H00E H 0.160697 0.462723 0.229706 0.088 Uiso 1 1 calc R U . . .
C00E C 0.1333(5) 0.4180(11) 0.4901(3) 0.072(2) Uani 1 1 d D U . . .
H00F H 0.103884 0.403713 0.461482 0.086 Uiso 1 1 calc R U . . .
C00F C 0.2169(4) 0.4608(10) 0.4885(2) 0.0546(15) Uani 1 1 d . U . . .
C00G C 0.5082(6) 0.5974(16) 0.4062(3) 0.090(3) Uani 1 1 d . . . . .
H00G H 0.525859 0.707080 0.388822 0.135 Uiso 1 1 calc R U . . .
H00H H 0.533856 0.487696 0.392562 0.135 Uiso 1 1 calc R U . . .
H00I H 0.524207 0.609007 0.439372 0.135 Uiso 1 1 calc R U . . .
C00H C 0.0910(5) 0.6030(13) 0.3811(2) 0.071(2) Uani 1 1 d . . . . .
C00I C 0.2597(7) 0.4816(16) 0.5315(2) 0.090(3) Uani 1 1 d D U . . .
H00J H 0.316269 0.507482 0.531223 0.108 Uiso 1 1 calc R U . . .
C00J C 0.0921(6) 0.3960(13) 0.5342(3) 0.091(3) Uani 1 1 d D U . . .
H00K H 0.036110 0.364151 0.534873 0.109 Uiso 1 1 calc R U . . .
C00K C 0.1348(8) 0.4214(16) 0.5764(3) 0.106(4) Uani 1 1 d D U . . .
H00L H 0.107433 0.410061 0.605803 0.128 Uiso 1 1 calc R U . . .
C00L C 0.2179(9) 0.4637(18) 0.5753(3) 0.108(4) Uani 1 1 d D U . . .
H00M H 0.246741 0.480551 0.603974 0.130 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
I001 C005 2.099(5) . ?
O002 C006 1.371(7) . ?
O002 C00G 1.436(11) . ?
O003 C00B 1.361(8) . ?
O003 C00D 1.421(9) . ?
N004 C009 1.397(8) . ?
N004 C00H 1.141(9) . ?
C005 C007 1.380(9) . ?
C005 C00B 1.382(9) . ?
C006 C007 1.373(9) . ?
C006 C008 1.416(8) . ?
C007 H007 0.9300 . ?
C008 C009 1.490(8) . ?
C008 C00A 1.393(8) . ?
C009 C00C 1.341(8) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.389(9) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.467(8) . ?
C00D H00B 0.9600 . ?
C00D H00D 0.9600 . ?
C00D H00E 0.9600 . ?
C00E H00F 0.9300 . ?
C00E C00F 1.382(11) . ?
C00E C00J 1.403(9) . ?
C00F C00I 1.386(11) . ?
C00G H00G 0.9600 . ?
C00G H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00I H00J 0.9300 . ?
C00I C00L 1.394(11) . ?
C00J H00K 0.9300 . ?
C00J C00K 1.371(13) . ?
C00K H00L 0.9300 . ?
C00K C00L 1.373(13) . ?
C00L H00M 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C006 O002 C00G 118.8(5) . . ?
C00B O003 C00D 118.4(5) . . ?
C00H N004 C009 176.8(6) . . ?
C007 C005 I001 119.1(5) . . ?
C007 C005 C00B 120.7(5) . . ?
C00B C005 I001 120.2(4) . . ?
O002 C006 C007 122.4(5) . . ?
O002 C006 C008 117.5(5) . . ?
C007 C006 C008 120.2(5) . . ?
C005 C007 H007 119.5 . . ?
C006 C007 C005 121.1(6) . . ?
C006 C007 H007 119.5 . . ?
C006 C008 C009 123.7(5) . . ?
C00A C008 C006 117.0(5) . . ?
C00A C008 C009 119.3(5) . . ?
N004 C009 C008 113.3(5) . . ?
C00C C009 N004 119.2(5) . . ?
C00C C009 C008 127.5(6) . . ?
C008 C00A H00A 118.5 . . ?
C00B C00A C008 122.9(6) . . ?
C00B C00A H00A 118.5 . . ?
O003 C00B C005 117.2(5) . . ?
O003 C00B C00A 124.7(6) . . ?
C005 C00B C00A 118.1(6) . . ?
C009 C00C H00C 114.7 . . ?
C009 C00C C00F 130.7(6) . . ?
C00F C00C H00C 114.7 . . ?
O003 C00D H00B 109.5 . . ?
O003 C00D H00D 109.5 . . ?
O003 C00D H00E 109.5 . . ?
H00B C00D H00D 109.5 . . ?
H00B C00D H00E 109.5 . . ?
H00D C00D H00E 109.5 . . ?
C00F C00E H00F 119.6 . . ?
C00F C00E C00J 120.8(8) . . ?
C00J C00E H00F 119.6 . . ?
C00E C00F C00C 124.8(6) . . ?
C00E C00F C00I 118.7(6) . . ?
C00I C00F C00C 116.4(7) . . ?
O002 C00G H00G 109.5 . . ?
O002 C00G H00H 109.5 . . ?
O002 C00G H00I 109.5 . . ?
H00G C00G H00H 109.5 . . ?
H00G C00G H00I 109.5 . . ?
H00H C00G H00I 109.5 . . ?
C00F C00I H00J 119.9 . . ?
C00F C00I C00L 120.1(10) . . ?
C00L C00I H00J 119.9 . . ?
C00E C00J H00K 120.1 . . ?
C00K C00J C00E 119.8(9) . . ?
C00K C00J H00K 120.1 . . ?
C00J C00K H00L 120.1 . . ?
C00J C00K C00L 119.8(8) . . ?
C00L C00K H00L 120.1 . . ?
C00I C00L H00M 119.6 . . ?
C00K C00L C00I 120.7(9) . . ?
C00K C00L H00M 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I001 C005 C007 C006 -178.1(5) . . . . ?
I001 C005 C00B O003 -3.2(7) . . . . ?
I001 C005 C00B C00A 177.4(4) . . . . ?
O002 C006 C007 C005 -177.9(5) . . . . ?
O002 C006 C008 C009 -2.5(9) . . . . ?
O002 C006 C008 C00A 177.2(5) . . . . ?
N004 C009 C00C C00F -1.1(11) . . . . ?
C006 C008 C009 N004 163.0(5) . . . . ?
C006 C008 C009 C00C -17.8(11) . . . . ?
C006 C008 C00A C00B 2.0(9) . . . . ?
C007 C005 C00B O003 179.1(5) . . . . ?
C007 C005 C00B C00A -0.3(9) . . . . ?
C007 C006 C008 C009 177.7(6) . . . . ?
C007 C006 C008 C00A -2.6(9) . . . . ?
C008 C006 C007 C005 1.8(9) . . . . ?
C008 C009 C00C C00F 179.8(7) . . . . ?
C008 C00A C00B O003 -179.9(6) . . . . ?
C008 C00A C00B C005 -0.6(9) . . . . ?
C009 C008 C00A C00B -178.3(6) . . . . ?
C009 C00C C00F C00E 25.9(13) . . . . ?
C009 C00C C00F C00I -155.0(9) . . . . ?
C00A C008 C009 N004 -16.7(8) . . . . ?
C00A C008 C009 C00C 162.5(7) . . . . ?
C00B C005 C007 C006 -0.4(9) . . . . ?
C00C C00F C00I C00L 179.4(10) . . . . ?
C00D O003 C00B C005 -173.6(6) . . . . ?
C00D O003 C00B C00A 5.7(9) . . . . ?
C00E C00F C00I C00L -1.5(15) . . . . ?
C00E C00J C00K C00L -1.6(17) . . . . ?
C00F C00E C00J C00K 1.6(14) . . . . ?
C00F C00I C00L C00K 1.4(19) . . . . ?
C00G O002 C006 C007 -0.8(10) . . . . ?
C00G O002 C006 C008 179.5(7) . . . . ?
C00J C00E C00F C00C 179.0(7) . . . . ?
C00J C00E C00F C00I 0.0(13) . . . . ?
C00J C00K C00L C00I 0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.664
_oxdiff_exptl_absorpt_empirical_full_min 0.183
####################################################################### 
# 
# 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_isk-431-01_auto
_database_code_depnum_ccdc_archive 'CCDC 2525261'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Seki'
;Shizuoka University
Japan
;
_audit_update_record             
;
2026-04-15 deposited with the CCDC.	2026-04-16 downloaded from the CCDC.
;
_audit_creation_date             2026-04-09
_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     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H28 I2 N2 O4'
_chemical_formula_sum            'C34 H28 I2 N2 O4'
_chemical_formula_weight         782.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C34H28I2N2O4
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.2144(3)
_cell_length_b                   14.0636(3)
_cell_length_c                   19.9281(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.398(2)
_cell_angle_gamma                90
_cell_volume                     3116.79(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13712
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.9490
_cell_measurement_theta_min      3.8310
_shelx_estimated_absorpt_T_max   0.389
_shelx_estimated_absorpt_T_min   0.072
_exptl_absorpt_coefficient_mu    16.175
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.037
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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            'clear dark black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -8 -4 0.1008
-3 8 3 0.1013
-3 1 -11 0.1597
3 -2 11 0.1541
-6 -4 4 0.0377
6 4 -4 0.0326
-2 2 -11 0.1565
3 -8 -4 0.1013

_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.072
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
2.8698 -8.0922 -3.7679 0.0103 0.5346 0.8450
-2.9694 8.1161 3.3413 -0.0111 -0.5661 -0.8243
-2.8050 1.0985 -11.0944 -0.0232 -0.8647 0.5018
2.9857 -1.6415 10.7847 0.0238 0.8967 -0.4421
-6.4381 -3.8629 3.9905 -0.9961 -0.0800 0.0364
6.4292 3.9075 -3.9231 0.9958 0.0800 -0.0435
-2.2889 1.7297 -11.4079 0.0722 -0.8776 0.4738
2.9589 -8.0803 -3.5810 0.0168 0.5507 0.8345

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20616
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.236
_diffrn_reflns_theta_min         3.858
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_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     38.00  69.00   0.50    0.47    --  107.14 -57.00  30.00   62
  2  ω     40.00  67.00   0.50    0.47    --  107.14 -77.00 -30.00   54
  3  ω     74.00 102.00   0.50    0.47    --  107.14 -77.00 -30.00   56
  4  ω     36.00  65.00   0.50    0.47    --  107.14 -57.00 -90.00   58
  5  ω     37.00  73.00   0.50    0.47    --  107.14 -61.00-121.00   72
  6  ω    -24.00  62.00   0.50    0.12    --   47.30 -61.00-121.00  172
  7  ω     44.00  69.00   0.50    0.47    --  107.14 -57.00  90.00   50
  8  ω    146.00 173.00   0.50    0.47    --  107.14  38.00 120.00   54
  9  ω    148.00 178.00   0.50    0.47    --  107.14  61.00  17.00   60
 10  ω    100.00 134.00   0.50    0.47    --  107.14  38.00 120.00   68
 11  ω     31.00  77.00   0.50    0.12    --   47.30  61.00  17.00   92
 12  ω    -21.00  27.00   0.50    0.12    --  -47.30  19.00-150.00   96
 13  ω    -17.00  12.00   0.50    0.12    --  -47.30  19.00-180.00   58
 14  ω    -18.00  27.00   0.50    0.12    --  -47.30  19.00  30.00   90
 15  ω    -22.00  20.00   0.50    0.12    --  -47.30  19.00   0.00   84
 16  ω     37.00 106.00   0.50    0.47    --  107.14 -99.00  60.00  138
 17  ω     41.00 103.00   0.50    0.47    --  107.14 -99.00-150.00  124
 18  ω    -58.00 -32.00   0.50    0.12    --  -47.30  61.00  17.00   52
 19  ω    -65.00 -33.00   0.50    0.47    -- -104.50  61.00  17.00   64
 20  ω    -60.00 -32.00   0.50    0.47    -- -104.50  57.00 120.00   56
 21  ω    -61.00 -35.00   0.50    0.47    -- -104.50  57.00 150.00   52
 22  ω    -58.00 -33.00   0.50    0.47    -- -104.50  57.00 -30.00   50
 23  ω    -61.00 -35.00   0.50    0.47    -- -104.50  57.00 -90.00   52
 24  ω    -59.00 -34.00   0.50    0.47    -- -104.50  57.00-120.00   50
 25  ω   -170.00 -98.00   0.50    0.47    -- -104.50 -57.00 -30.00  144
 26  ω   -120.00 -45.00   0.50    0.12    --  -47.30 -61.00-121.00  150
 27  ω   -174.00 -90.00   0.50    0.47    -- -104.50 -61.00-121.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1122721000
_diffrn_orient_matrix_UB_12      0.0485547000
_diffrn_orient_matrix_UB_13      -0.0214892000
_diffrn_orient_matrix_UB_21      0.0810274000
_diffrn_orient_matrix_UB_22      -0.0612585000
_diffrn_orient_matrix_UB_23      0.0513874000
_diffrn_orient_matrix_UB_31      0.0065996000
_diffrn_orient_matrix_UB_32      -0.0767113000
_diffrn_orient_matrix_UB_33      -0.0544927000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4912
_reflns_number_total             5683
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_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 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         2.057
_refine_diff_density_min         -1.418
_refine_diff_density_rms         0.175
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.011
_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)+(0.1219P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1549
_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 Ternary CH refined with riding coordinates:
 C00D(H00D), C00I(H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00H(H00H), C00M(H00M), C00O(H00O), C00P(H00P), C00S(H00S),
 C00U(H00U), C00Y(H00Y), C00Z(H00Z), C011(H011), C012(H012), C013(H013),
 C014(H014), C016(H016)
2.c Idealised Me refined as rotating group:
 C00T(H00A,H00B,H00E), C00W(H00F,H00G,H00J), C010(H01A,H01B,H01C), C015(H01D,
 H01E,H01F)
;
_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
I001 I 0.35540(3) 0.66459(2) -0.03929(2) 0.04613(16) Uani 1 1 d . . . . .
I002 I 0.32983(3) 0.95288(2) 0.50027(2) 0.04773(15) Uani 1 1 d . . . . .
O003 O 0.5459(3) 0.4904(2) 0.19228(17) 0.0412(7) Uani 1 1 d . . . . .
O004 O 0.3946(3) 0.7629(3) 0.27079(18) 0.0470(8) Uani 1 1 d . . . . .
O005 O 0.4510(4) 0.8316(2) 0.05722(19) 0.0469(8) Uani 1 1 d . . . . .
O006 O 0.5274(4) 0.8002(3) 0.54605(17) 0.0484(8) Uani 1 1 d . . . . .
N007 N 0.6810(4) 0.7535(3) 0.2793(2) 0.0364(8) Uani 1 1 d . . . . .
N008 N 0.4721(4) 0.5641(3) 0.3157(2) 0.0373(8) Uani 1 1 d . . . . .
C009 C 0.4419(4) 0.6646(3) 0.0608(2) 0.0373(10) Uani 1 1 d . . . . .
C00A C 0.8540(4) 0.5989(3) 0.2754(2) 0.0377(10) Uani 1 1 d . . . . .
C00B C 0.5219(4) 0.5754(3) 0.1597(2) 0.0345(9) Uani 1 1 d . . . . .
C00C C 0.5475(4) 0.7205(3) 0.4392(2) 0.0381(10) Uani 1 1 d . . . . .
H00C H 0.605638 0.677661 0.460861 0.046 Uiso 1 1 calc R U . . .
C00D C 0.6892(4) 0.5888(3) 0.3600(2) 0.0343(9) Uani 1 1 d . . . . .
H00D H 0.738955 0.638868 0.385914 0.041 Uiso 1 1 calc R U . . .
C00E C 0.6962(4) 0.4999(3) 0.4015(2) 0.0388(10) Uani 1 1 d . . . . .
C00F C 0.4144(5) 0.8514(3) 0.4449(2) 0.0389(10) Uani 1 1 d . . . . .
C00G C 0.4986(5) 0.7899(4) 0.4779(2) 0.0399(10) Uani 1 1 d . . . . .
C00H C 0.4641(4) 0.5776(4) 0.0934(2) 0.0376(10) Uani 1 1 d . . . . .
H00H H 0.439887 0.520051 0.070589 0.045 Uiso 1 1 calc R U . . .
C00I C 0.7248(4) 0.5842(3) 0.2881(2) 0.0351(9) Uani 1 1 d . . . . .
H00I H 0.696386 0.521988 0.267498 0.042 Uiso 1 1 calc R U . . .
C00J C 0.4275(4) 0.7755(3) 0.3388(2) 0.0379(10) Uani 1 1 d . . . . .
C00K C 0.6277(4) 0.6615(3) 0.2645(2) 0.0344(9) Uani 1 1 d . . . . .
C00L C 0.5132(4) 0.7126(3) 0.3702(2) 0.0361(9) Uani 1 1 d . . . . .
C00M C 0.5395(4) 0.7449(3) 0.1573(2) 0.0370(10) Uani 1 1 d . . . . .
H00M H 0.566903 0.802625 0.178658 0.044 Uiso 1 1 calc R U . . .
C00N C 0.5624(4) 0.6600(3) 0.1927(2) 0.0334(9) Uani 1 1 d . . . . .
C00O C 0.3780(5) 0.8451(3) 0.3763(3) 0.0418(11) Uani 1 1 d . . . . .
H00O H 0.319630 0.888004 0.354840 0.050 Uiso 1 1 calc R U . . .
C00P C 0.6743(5) 0.4092(4) 0.3725(3) 0.0457(11) Uani 1 1 d . . . . .
H00P H 0.646001 0.403932 0.325596 0.055 Uiso 1 1 calc R U . . .
C00Q C 0.4783(4) 0.7489(3) 0.0921(2) 0.0363(10) Uani 1 1 d . . . . .
C00R C 0.5650(4) 0.6343(3) 0.3300(2) 0.0359(9) Uani 1 1 d . . . . .
C00S C 0.9420(5) 0.6359(4) 0.3234(3) 0.0417(10) Uani 1 1 d . . . . .
H00S H 0.922060 0.653619 0.366559 0.050 Uiso 1 1 calc R U . . .
C00T C 0.4914(5) 0.9186(4) 0.0899(3) 0.0467(12) Uani 1 1 d . . . . .
H00A H 0.465539 0.972355 0.060239 0.070 Uiso 1 1 calc R U . . .
H00B H 0.579346 0.918135 0.099327 0.070 Uiso 1 1 calc R U . . .
H00E H 0.456973 0.924880 0.132444 0.070 Uiso 1 1 calc R U . . .
C00U C 0.8852(5) 0.5730(4) 0.2123(3) 0.0477(12) Uani 1 1 d . . . . .
H00U H 0.826032 0.546711 0.179066 0.057 Uiso 1 1 calc R U . . .
C00V C 0.3944(5) 0.5098(4) 0.3142(3) 0.0519(13) Uani 1 1 d . . . . .
C00W C 0.3139(5) 0.8307(4) 0.2361(3) 0.0498(13) Uani 1 1 d . . . . .
H00F H 0.307491 0.819355 0.187195 0.075 Uiso 1 1 calc R U . . .
H00G H 0.344454 0.895042 0.246180 0.075 Uiso 1 1 calc R U . . .
H00J H 0.234376 0.824023 0.250986 0.075 Uiso 1 1 calc R U . . .
C00X C 0.7295(6) 0.8234(4) 0.2956(3) 0.0521(13) Uani 1 1 d . . . . .
C00Y C 0.7333(5) 0.5050(4) 0.4715(3) 0.0482(12) Uani 1 1 d . . . . .
H00Y H 0.746810 0.565329 0.492675 0.058 Uiso 1 1 calc R U . . .
C00Z C 1.0585(5) 0.6474(4) 0.3091(3) 0.0515(13) Uani 1 1 d . . . . .
H00Z H 1.117539 0.673750 0.342369 0.062 Uiso 1 1 calc R U . . .
C010 C 0.4605(5) 0.4157(4) 0.1780(3) 0.0464(12) Uani 1 1 d . . . . .
H01A H 0.467651 0.388882 0.133296 0.070 Uiso 1 1 calc R U . . .
H01B H 0.379187 0.440895 0.178504 0.070 Uiso 1 1 calc R U . . .
H01C H 0.476022 0.365836 0.212405 0.070 Uiso 1 1 calc R U . . .
C011 C 1.0025(6) 0.5854(5) 0.1974(3) 0.0576(14) Uani 1 1 d . . . . .
H011 H 1.022254 0.569709 0.153829 0.069 Uiso 1 1 calc R U . . .
C012 C 1.0901(5) 0.6207(5) 0.2465(3) 0.0541(14) Uani 1 1 d . . . . .
H012 H 1.170940 0.626659 0.237511 0.065 Uiso 1 1 calc R U . . .
C013 C 0.6936(6) 0.3273(4) 0.4113(4) 0.0564(15) Uani 1 1 d . . . . .
H013 H 0.680341 0.266494 0.390929 0.068 Uiso 1 1 calc R U . . .
C014 C 0.7506(6) 0.4226(5) 0.5101(3) 0.0595(15) Uani 1 1 d . . . . .
H014 H 0.775152 0.426848 0.557475 0.071 Uiso 1 1 calc R U . . .
C015 C 0.6040(6) 0.7283(5) 0.5811(3) 0.0587(15) Uani 1 1 d . . . . .
H01D H 0.685412 0.734278 0.568668 0.088 Uiso 1 1 calc R U . . .
H01E H 0.571976 0.665134 0.568224 0.088 Uiso 1 1 calc R U . . .
H01F H 0.606369 0.736879 0.630021 0.088 Uiso 1 1 calc R U . . .
C016 C 0.7320(6) 0.3346(5) 0.4799(4) 0.0673(19) Uani 1 1 d . . . . .
H016 H 0.745847 0.278650 0.506390 0.081 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
I001 C009 2.103(5) . ?
I002 C00F 2.103(5) . ?
O003 C00B 1.371(6) . ?
O003 C010 1.425(6) . ?
O004 C00J 1.371(6) . ?
O004 C00W 1.430(6) . ?
O005 C00Q 1.369(6) . ?
O005 C00T 1.432(6) . ?
O006 C00G 1.363(6) . ?
O006 C015 1.446(7) . ?
N007 C00K 1.440(6) . ?
N007 C00X 1.150(7) . ?
N008 C00R 1.437(6) . ?
N008 C00V 1.156(7) . ?
C009 C00H 1.392(7) . ?
C009 C00Q 1.377(7) . ?
C00A C00I 1.517(7) . ?
C00A C00S 1.384(7) . ?
C00A C00U 1.397(7) . ?
C00B C00H 1.396(7) . ?
C00B C00N 1.406(7) . ?
C00C H00C 0.9500 . ?
C00C C00G 1.398(7) . ?
C00C C00L 1.384(7) . ?
C00D H00D 1.0000 . ?
C00D C00E 1.496(6) . ?
C00D C00I 1.538(6) . ?
C00D C00R 1.579(6) . ?
C00E C00P 1.410(8) . ?
C00E C00Y 1.405(7) . ?
C00F C00G 1.382(7) . ?
C00F C00O 1.378(7) . ?
C00H H00H 0.9500 . ?
C00I H00I 1.0000 . ?
C00I C00K 1.568(6) . ?
C00J C00L 1.394(7) . ?
C00J C00O 1.389(7) . ?
C00K C00N 1.521(6) . ?
C00K C00R 1.607(7) . ?
C00L C00R 1.519(6) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.394(7) . ?
C00M C00Q 1.389(7) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00P C013 1.389(8) . ?
C00S H00S 0.9500 . ?
C00S C00Z 1.382(8) . ?
C00T H00A 0.9800 . ?
C00T H00B 0.9800 . ?
C00T H00E 0.9800 . ?
C00U H00U 0.9500 . ?
C00U C011 1.396(8) . ?
C00W H00F 0.9800 . ?
C00W H00G 0.9800 . ?
C00W H00J 0.9800 . ?
C00Y H00Y 0.9500 . ?
C00Y C014 1.391(8) . ?
C00Z H00Z 0.9500 . ?
C00Z C012 1.392(9) . ?
C010 H01A 0.9800 . ?
C010 H01B 0.9800 . ?
C010 H01C 0.9800 . ?
C011 H011 0.9500 . ?
C011 C012 1.386(9) . ?
C012 H012 0.9500 . ?
C013 H013 0.9500 . ?
C013 C016 1.382(11) . ?
C014 H014 0.9500 . ?
C014 C016 1.380(11) . ?
C015 H01D 0.9800 . ?
C015 H01E 0.9800 . ?
C015 H01F 0.9800 . ?
C016 H016 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
C00B O003 C010 117.6(4) . . ?
C00J O004 C00W 117.7(4) . . ?
C00Q O005 C00T 117.2(4) . . ?
C00G O006 C015 117.2(4) . . ?
C00X N007 C00K 174.3(5) . . ?
C00V N008 C00R 169.7(5) . . ?
C00H C009 I001 118.4(4) . . ?
C00Q C009 I001 120.2(3) . . ?
C00Q C009 C00H 121.4(4) . . ?
C00S C00A C00I 123.2(4) . . ?
C00S C00A C00U 118.7(5) . . ?
C00U C00A C00I 118.0(5) . . ?
O003 C00B C00H 120.5(4) . . ?
O003 C00B C00N 119.0(4) . . ?
C00H C00B C00N 120.4(4) . . ?
C00G C00C H00C 119.1 . . ?
C00L C00C H00C 119.1 . . ?
C00L C00C C00G 121.7(4) . . ?
C00E C00D H00D 108.5 . . ?
C00E C00D C00I 118.6(4) . . ?
C00E C00D C00R 122.0(4) . . ?
C00I C00D H00D 108.5 . . ?
C00I C00D C00R 89.2(3) . . ?
C00R C00D H00D 108.5 . . ?
C00P C00E C00D 122.4(5) . . ?
C00Y C00E C00D 119.6(4) . . ?
C00Y C00E C00P 117.9(5) . . ?
C00G C00F I002 120.1(3) . . ?
C00O C00F I002 117.9(4) . . ?
C00O C00F C00G 121.9(4) . . ?
O006 C00G C00C 124.3(4) . . ?
O006 C00G C00F 117.8(4) . . ?
C00F C00G C00C 117.8(4) . . ?
C009 C00H C00B 119.6(4) . . ?
C009 C00H H00H 120.2 . . ?
C00B C00H H00H 120.2 . . ?
C00A C00I C00D 121.2(4) . . ?
C00A C00I H00I 108.2 . . ?
C00A C00I C00K 119.7(4) . . ?
C00D C00I H00I 108.2 . . ?
C00D C00I C00K 89.8(3) . . ?
C00K C00I H00I 108.2 . . ?
O004 C00J C00L 116.3(4) . . ?
O004 C00J C00O 123.2(4) . . ?
C00O C00J C00L 120.5(4) . . ?
N007 C00K C00I 108.0(4) . . ?
N007 C00K C00N 110.0(4) . . ?
N007 C00K C00R 105.1(4) . . ?
C00I C00K C00R 87.2(3) . . ?
C00N C00K C00I 120.2(4) . . ?
C00N C00K C00R 123.6(4) . . ?
C00C C00L C00J 118.7(4) . . ?
C00C C00L C00R 120.4(4) . . ?
C00J C00L C00R 120.8(4) . . ?
C00N C00M H00M 118.5 . . ?
C00Q C00M H00M 118.5 . . ?
C00Q C00M C00N 123.0(4) . . ?
C00B C00N C00K 122.6(4) . . ?
C00M C00N C00B 117.4(4) . . ?
C00M C00N C00K 119.9(4) . . ?
C00F C00O C00J 119.3(4) . . ?
C00F C00O H00O 120.3 . . ?
C00J C00O H00O 120.3 . . ?
C00E C00P H00P 119.5 . . ?
C013 C00P C00E 121.0(5) . . ?
C013 C00P H00P 119.5 . . ?
O005 C00Q C009 117.8(4) . . ?
O005 C00Q C00M 124.1(4) . . ?
C009 C00Q C00M 118.1(4) . . ?
N008 C00R C00D 112.2(4) . . ?
N008 C00R C00K 112.6(4) . . ?
N008 C00R C00L 106.6(4) . . ?
C00D C00R C00K 87.0(3) . . ?
C00L C00R C00D 118.2(4) . . ?
C00L C00R C00K 119.5(4) . . ?
C00A C00S H00S 119.6 . . ?
C00Z C00S C00A 120.7(5) . . ?
C00Z C00S H00S 119.6 . . ?
O005 C00T H00A 109.5 . . ?
O005 C00T H00B 109.5 . . ?
O005 C00T H00E 109.5 . . ?
H00A C00T H00B 109.5 . . ?
H00A C00T H00E 109.5 . . ?
H00B C00T H00E 109.5 . . ?
C00A C00U H00U 119.6 . . ?
C011 C00U C00A 120.7(5) . . ?
C011 C00U H00U 119.6 . . ?
O004 C00W H00F 109.5 . . ?
O004 C00W H00G 109.5 . . ?
O004 C00W H00J 109.5 . . ?
H00F C00W H00G 109.5 . . ?
H00F C00W H00J 109.5 . . ?
H00G C00W H00J 109.5 . . ?
C00E C00Y H00Y 119.7 . . ?
C014 C00Y C00E 120.5(6) . . ?
C014 C00Y H00Y 119.7 . . ?
C00S C00Z H00Z 119.7 . . ?
C00S C00Z C012 120.6(6) . . ?
C012 C00Z H00Z 119.7 . . ?
O003 C010 H01A 109.5 . . ?
O003 C010 H01B 109.5 . . ?
O003 C010 H01C 109.5 . . ?
H01A C010 H01B 109.5 . . ?
H01A C010 H01C 109.5 . . ?
H01B C010 H01C 109.5 . . ?
C00U C011 H011 120.1 . . ?
C012 C011 C00U 119.8(6) . . ?
C012 C011 H011 120.1 . . ?
C00Z C012 H012 120.3 . . ?
C011 C012 C00Z 119.3(5) . . ?
C011 C012 H012 120.3 . . ?
C00P C013 H013 120.2 . . ?
C016 C013 C00P 119.7(6) . . ?
C016 C013 H013 120.2 . . ?
C00Y C014 H014 119.9 . . ?
C016 C014 C00Y 120.2(6) . . ?
C016 C014 H014 119.9 . . ?
O006 C015 H01D 109.5 . . ?
O006 C015 H01E 109.5 . . ?
O006 C015 H01F 109.5 . . ?
H01D C015 H01E 109.5 . . ?
H01D C015 H01F 109.5 . . ?
H01E C015 H01F 109.5 . . ?
C013 C016 H016 119.7 . . ?
C014 C016 C013 120.6(5) . . ?
C014 C016 H016 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I001 C009 C00H C00B 179.7(3) . . . . ?
I001 C009 C00Q O005 3.1(6) . . . . ?
I001 C009 C00Q C00M -177.4(3) . . . . ?
I002 C00F C00G O006 -2.5(6) . . . . ?
I002 C00F C00G C00C 176.6(4) . . . . ?
I002 C00F C00O C00J -176.6(4) . . . . ?
O003 C00B C00H C009 -179.1(4) . . . . ?
O003 C00B C00N C00K -2.5(7) . . . . ?
O003 C00B C00N C00M 178.2(4) . . . . ?
O004 C00J C00L C00C -178.3(4) . . . . ?
O004 C00J C00L C00R -0.6(7) . . . . ?
O004 C00J C00O C00F 178.5(5) . . . . ?
N007 C00K C00N C00B 167.4(4) . . . . ?
N007 C00K C00N C00M -13.3(6) . . . . ?
N007 C00K C00R N008 158.5(4) . . . . ?
N007 C00K C00R C00D -88.7(4) . . . . ?
N007 C00K C00R C00L 32.2(5) . . . . ?
C00A C00I C00K N007 -41.1(6) . . . . ?
C00A C00I C00K C00N 86.2(6) . . . . ?
C00A C00I C00K C00R -146.1(4) . . . . ?
C00A C00S C00Z C012 -0.9(8) . . . . ?
C00A C00U C011 C012 2.2(9) . . . . ?
C00C C00L C00R N008 104.6(5) . . . . ?
C00C C00L C00R C00D -22.8(6) . . . . ?
C00C C00L C00R C00K -126.3(5) . . . . ?
C00D C00E C00P C013 173.3(5) . . . . ?
C00D C00E C00Y C014 -174.4(5) . . . . ?
C00D C00I C00K N007 85.3(4) . . . . ?
C00D C00I C00K C00N -147.4(4) . . . . ?
C00D C00I C00K C00R -19.7(3) . . . . ?
C00E C00D C00I C00A -88.1(6) . . . . ?
C00E C00D C00I C00K 146.6(4) . . . . ?
C00E C00D C00R N008 -30.1(6) . . . . ?
C00E C00D C00R C00K -143.3(4) . . . . ?
C00E C00D C00R C00L 94.6(5) . . . . ?
C00E C00P C013 C016 1.5(9) . . . . ?
C00E C00Y C014 C016 0.4(9) . . . . ?
C00G C00C C00L C00J -0.3(7) . . . . ?
C00G C00C C00L C00R -178.0(5) . . . . ?
C00G C00F C00O C00J -0.4(8) . . . . ?
C00H C009 C00Q O005 -178.7(4) . . . . ?
C00H C009 C00Q C00M 0.8(7) . . . . ?
C00H C00B C00N C00K -179.0(4) . . . . ?
C00H C00B C00N C00M 1.7(7) . . . . ?
C00I C00A C00S C00Z 179.7(5) . . . . ?
C00I C00A C00U C011 179.6(5) . . . . ?
C00I C00D C00E C00P -32.5(7) . . . . ?
C00I C00D C00E C00Y 143.2(5) . . . . ?
C00I C00D C00R N008 93.7(4) . . . . ?
C00I C00D C00R C00K -19.5(3) . . . . ?
C00I C00D C00R C00L -141.6(4) . . . . ?
C00I C00K C00N C00B 41.1(7) . . . . ?
C00I C00K C00N C00M -139.7(5) . . . . ?
C00I C00K C00R N008 -93.6(4) . . . . ?
C00I C00K C00R C00D 19.2(3) . . . . ?
C00I C00K C00R C00L 140.1(4) . . . . ?
C00J C00L C00R N008 -73.1(5) . . . . ?
C00J C00L C00R C00D 159.5(4) . . . . ?
C00J C00L C00R C00K 56.0(6) . . . . ?
C00L C00C C00G O006 178.9(5) . . . . ?
C00L C00C C00G C00F -0.2(8) . . . . ?
C00L C00J C00O C00F -0.1(8) . . . . ?
C00N C00B C00H C009 -2.7(7) . . . . ?
C00N C00K C00R N008 31.3(6) . . . . ?
C00N C00K C00R C00D 144.1(4) . . . . ?
C00N C00K C00R C00L -95.0(5) . . . . ?
C00N C00M C00Q O005 177.6(5) . . . . ?
C00N C00M C00Q C009 -1.9(7) . . . . ?
C00O C00F C00G O006 -178.7(5) . . . . ?
C00O C00F C00G C00C 0.5(8) . . . . ?
C00O C00J C00L C00C 0.4(7) . . . . ?
C00O C00J C00L C00R 178.1(5) . . . . ?
C00P C00E C00Y C014 1.6(8) . . . . ?
C00P C013 C016 C014 0.5(10) . . . . ?
C00Q C009 C00H C00B 1.4(7) . . . . ?
C00Q C00M C00N C00B 0.6(7) . . . . ?
C00Q C00M C00N C00K -178.7(4) . . . . ?
C00R C00D C00E C00P 76.3(6) . . . . ?
C00R C00D C00E C00Y -108.0(5) . . . . ?
C00R C00D C00I C00A 145.3(4) . . . . ?
C00R C00D C00I C00K 20.0(3) . . . . ?
C00R C00K C00N C00B -67.5(6) . . . . ?
C00R C00K C00N C00M 111.7(5) . . . . ?
C00S C00A C00I C00D -13.6(7) . . . . ?
C00S C00A C00I C00K 96.3(6) . . . . ?
C00S C00A C00U C011 -0.9(8) . . . . ?
C00S C00Z C012 C011 2.2(9) . . . . ?
C00T O005 C00Q C009 -178.8(5) . . . . ?
C00T O005 C00Q C00M 1.7(7) . . . . ?
C00U C00A C00I C00D 165.9(5) . . . . ?
C00U C00A C00I C00K -84.2(6) . . . . ?
C00U C00A C00S C00Z 0.2(8) . . . . ?
C00U C011 C012 C00Z -2.9(9) . . . . ?
C00V N008 C00R C00D 88(3) . . . . ?
C00V N008 C00R C00K -175(3) . . . . ?
C00V N008 C00R C00L -42(3) . . . . ?
C00W O004 C00J C00L -175.2(5) . . . . ?
C00W O004 C00J C00O 6.1(7) . . . . ?
C00Y C00E C00P C013 -2.5(8) . . . . ?
C00Y C014 C016 C013 -1.5(10) . . . . ?
C010 O003 C00B C00H -35.0(6) . . . . ?
C010 O003 C00B C00N 148.5(4) . . . . ?
C015 O006 C00G C00C -6.6(8) . . . . ?
C015 O006 C00G C00F 172.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.416
_oxdiff_exptl_absorpt_empirical_full_min 0.453
####################################################################### 
# 
# 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_isk-466-04-223k-3_auto
_database_code_depnum_ccdc_archive 'CCDC 2525259'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Seki'
;Shizuoka University
Japan
;
_audit_update_record             
;
2026-04-15 deposited with the CCDC.	2026-04-16 downloaded from the CCDC.
;
_audit_creation_date             2026-04-14
_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     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 I N O2'
_chemical_formula_sum            'C17 H14 I N O2'
_chemical_formula_weight         391.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H14INO2
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.1063(6)
_cell_length_b                   7.0543(5)
_cell_length_c                   27.6933(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3146.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3223
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      75.7550
_cell_measurement_theta_min      3.1860
_shelx_estimated_absorpt_T_max   0.740
_shelx_estimated_absorpt_T_min   0.058
_exptl_absorpt_coefficient_mu    16.023
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.052
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 0 10 0.0207
-1 -5 2 0.2188
1 5 -2 0.2264
-6 0 14 0.0223
6 0 -14 0.0171
-9 0 -10 0.0185

_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
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
8.5855 0.0245 10.2402 0.1378 0.3813 -0.9141
-0.8738 -4.5458 1.8462 -0.3047 -0.8685 -0.3911
0.8585 4.5459 -1.8644 0.3044 0.8678 0.3928
-6.3564 0.1799 14.2309 0.9032 -0.4292 0.0090
6.3564 -0.1799 -14.2309 -0.9032 0.4292 -0.0090
-8.6016 0.1059 -10.1926 -0.1230 -0.3594 0.9250

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            10257
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.406
_diffrn_reflns_theta_min         3.192
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -44.00   0.50    2.20    --  -47.55 -75.00 -73.00  140
  2  ω    -62.00 -32.00   0.50    8.82    -- -104.50  58.00-164.00   60
  3  ω    -64.00 -34.00   0.50    8.82    -- -104.50  91.00 -60.00   60
  4  ω   -156.00 -85.00   0.50    8.82    -- -104.50 -75.00 -73.00  142
  5  ω     35.00  64.00   0.50    8.82    --  107.14 -58.00  54.00   58
  6  ω    -22.00  20.00   0.50    2.20    --  -47.55  19.00-150.00   84
  7  ω    -36.00  22.00   0.50    2.20    --  -47.55  38.00 -90.00  116
  8  ω     26.00  58.00   0.50    2.20    --   47.55-125.00 -60.00   64
  9  ω    -62.00 -33.00   0.50    8.82    -- -104.50  57.00 150.00   58
 10  ω    -60.00 -35.00   0.50    8.82    -- -104.50  57.00 120.00   50
 11  ω    -61.00 -33.00   0.50    8.82    -- -104.50  57.00 -90.00   56
 12  ω     81.00 106.00   0.50    8.82    --  107.14 -99.00-180.00   50
 13  ω     40.00  67.00   0.50    8.82    --  107.14 -57.00  90.00   54
 14  ω     37.00 107.00   0.50    8.82    --  107.14 -77.00-180.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0381729000
_diffrn_orient_matrix_UB_12      0.0927325000
_diffrn_orient_matrix_UB_13      0.0452415000
_diffrn_orient_matrix_UB_21      0.0538572000
_diffrn_orient_matrix_UB_22      0.1773020000
_diffrn_orient_matrix_UB_23      -0.0083470000
_diffrn_orient_matrix_UB_31      -0.0692700000
_diffrn_orient_matrix_UB_32      0.0866007000
_diffrn_orient_matrix_UB_33      -0.0313996000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2400
_reflns_number_total             3118
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_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 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         2.260
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.206
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3118
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0805
_refine_ls_restrained_S_all      1.077
_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)+(0.1142P)²+13.7718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2050
_refine_ls_wR_factor_ref         0.2185
_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. Restrained distances
 C00I-C00K
 1.39 with sigma of 0.01
 C00K-C00L
 1.39 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C008 \\sim C00G \\sim C00H \\sim C00I \\sim C00K \\sim C00L: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C00B(H00D), C00C(H00E), C00E(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00M), C00L(H00N)
4.b Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C), C00J(H00J,H00K,H00L)
;
_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
I001 I 0.46423(3) 0.60167(10) 0.79005(2) 0.0465(3) Uani 1 1 d . . . . .
O002 O 0.2719(4) 0.5850(13) 0.7769(2) 0.0548(19) Uani 1 1 d . . . . .
O003 O 0.4194(4) 0.5801(13) 0.5960(2) 0.058(2) Uani 1 1 d . . . . .
N004 N 0.1582(5) 0.5755(12) 0.6095(3) 0.0432(18) Uani 1 1 d . . . . .
C005 C 0.3909(5) 0.5905(14) 0.7285(3) 0.0407(19) Uani 1 1 d . . . . .
C006 C 0.3824(5) 0.5759(14) 0.6409(3) 0.042(2) Uani 1 1 d . . . . .
C007 C 0.3046(5) 0.5789(14) 0.7314(3) 0.0396(19) Uani 1 1 d . . . . .
C008 C 0.2153(6) 0.4674(15) 0.5111(3) 0.046(2) Uani 1 1 d . U . . .
C009 C 0.2960(5) 0.5601(11) 0.6434(3) 0.0355(18) Uani 1 1 d . . . . .
C00A C 0.1834(6) 0.5837(19) 0.7807(4) 0.054(3) Uani 1 1 d . . . . .
H00A H 0.160631 0.687111 0.761807 0.081 Uiso 1 1 calc R U . . .
H00B H 0.167455 0.598789 0.814244 0.081 Uiso 1 1 calc R U . . .
H00C H 0.162110 0.464168 0.768571 0.081 Uiso 1 1 calc R U . . .
C00B C 0.2591(5) 0.5649(15) 0.6888(3) 0.044(2) Uani 1 1 d . . . . .
H00D H 0.200935 0.558469 0.690853 0.053 Uiso 1 1 calc R U . . .
C00C C 0.4291(5) 0.5907(14) 0.6831(3) 0.041(2) Uani 1 1 d . . . . .
H00E H 0.487148 0.600948 0.681058 0.049 Uiso 1 1 calc R U . . .
C00D C 0.2418(6) 0.5374(15) 0.5998(3) 0.044(2) Uani 1 1 d . . . . .
C00E C 0.2657(6) 0.4883(16) 0.5551(3) 0.049(2) Uani 1 1 d . . . . .
H00F H 0.322722 0.463952 0.551320 0.058 Uiso 1 1 calc R U . . .
C00F C 0.0899(6) 0.606(2) 0.6192(4) 0.060(3) Uani 1 1 d . . . . .
C00G C 0.1316(7) 0.417(2) 0.5104(4) 0.064(3) Uani 1 1 d . U . . .
H00G H 0.103136 0.396317 0.539516 0.076 Uiso 1 1 calc R U . . .
C00H C 0.2567(10) 0.490(2) 0.4671(4) 0.081(4) Uani 1 1 d . U . . .
H00H H 0.313633 0.519246 0.467058 0.097 Uiso 1 1 calc R U . . .
C00I C 0.0900(8) 0.397(2) 0.4664(4) 0.083(4) Uani 1 1 d D U . . .
H00I H 0.033435 0.364258 0.466013 0.100 Uiso 1 1 calc R U . . .
C00J C 0.5080(7) 0.597(3) 0.5930(4) 0.080(5) Uani 1 1 d . . . . .
H00J H 0.524283 0.611676 0.559491 0.120 Uiso 1 1 calc R U . . .
H00K H 0.533644 0.483936 0.606215 0.120 Uiso 1 1 calc R U . . .
H00L H 0.525964 0.706909 0.611280 0.120 Uiso 1 1 calc R U . . .
C00K C 0.1318(9) 0.426(3) 0.4236(4) 0.098(5) Uani 1 1 d D U . . .
H00M H 0.103497 0.415394 0.394000 0.117 Uiso 1 1 calc R U . . .
C00L C 0.2156(10) 0.469(3) 0.4241(5) 0.098(5) Uani 1 1 d D U . . .
H00N H 0.244418 0.485042 0.394904 0.118 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
I001 C005 2.075(8) . ?
O002 C007 1.368(11) . ?
O002 C00A 1.428(12) . ?
O003 C006 1.380(11) . ?
O003 C00J 1.434(14) . ?
N004 C00D 1.398(12) . ?
N004 C00F 1.153(13) . ?
C005 C007 1.394(12) . ?
C005 C00C 1.399(13) . ?
C006 C009 1.397(12) . ?
C006 C00C 1.394(13) . ?
C007 C00B 1.391(12) . ?
C008 C00E 1.472(13) . ?
C008 C00G 1.394(15) . ?
C008 C00H 1.397(15) . ?
C009 C00B 1.393(12) . ?
C009 C00D 1.498(12) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A H00C 0.9700 . ?
C00B H00D 0.9400 . ?
C00C H00E 0.9400 . ?
C00D C00E 1.343(13) . ?
C00E H00F 0.9400 . ?
C00G H00G 0.9400 . ?
C00G C00I 1.397(15) . ?
C00H H00H 0.9400 . ?
C00H C00L 1.370(18) . ?
C00I H00I 0.9400 . ?
C00I C00K 1.379(9) . ?
C00J H00J 0.9700 . ?
C00J H00K 0.9700 . ?
C00J H00L 0.9700 . ?
C00K H00M 0.9400 . ?
C00K C00L 1.384(9) . ?
C00L H00N 0.9400 . ?

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
C007 O002 C00A 116.8(7) . . ?
C006 O003 C00J 118.9(7) . . ?
C00F N004 C00D 177.7(9) . . ?
C007 C005 I001 121.5(6) . . ?
C007 C005 C00C 119.3(8) . . ?
C00C C005 I001 119.2(6) . . ?
O003 C006 C009 118.4(8) . . ?
O003 C006 C00C 121.4(8) . . ?
C00C C006 C009 120.2(8) . . ?
O002 C007 C005 115.8(8) . . ?
O002 C007 C00B 125.5(8) . . ?
C00B C007 C005 118.8(8) . . ?
C00G C008 C00E 124.8(9) . . ?
C00G C008 C00H 118.6(10) . . ?
C00H C008 C00E 116.5(11) . . ?
C006 C009 C00D 123.4(8) . . ?
C00B C009 C006 117.8(8) . . ?
C00B C009 C00D 118.8(8) . . ?
O002 C00A H00A 109.5 . . ?
O002 C00A H00B 109.5 . . ?
O002 C00A H00C 109.5 . . ?
H00A C00A H00B 109.5 . . ?
H00A C00A H00C 109.5 . . ?
H00B C00A H00C 109.5 . . ?
C007 C00B C009 122.9(8) . . ?
C007 C00B H00D 118.6 . . ?
C009 C00B H00D 118.6 . . ?
C005 C00C H00E 119.5 . . ?
C006 C00C C005 121.1(8) . . ?
C006 C00C H00E 119.5 . . ?
N004 C00D C009 112.7(7) . . ?
C00E C00D N004 120.2(8) . . ?
C00E C00D C009 127.1(9) . . ?
C008 C00E H00F 115.4 . . ?
C00D C00E C008 129.1(9) . . ?
C00D C00E H00F 115.4 . . ?
C008 C00G H00G 119.9 . . ?
C008 C00G C00I 120.1(11) . . ?
C00I C00G H00G 119.9 . . ?
C008 C00H H00H 119.5 . . ?
C00L C00H C008 120.9(14) . . ?
C00L C00H H00H 119.5 . . ?
C00G C00I H00I 120.0 . . ?
C00K C00I C00G 120.0(12) . . ?
C00K C00I H00I 120.0 . . ?
O003 C00J H00J 109.5 . . ?
O003 C00J H00K 109.5 . . ?
O003 C00J H00L 109.5 . . ?
H00J C00J H00K 109.5 . . ?
H00J C00J H00L 109.5 . . ?
H00K C00J H00L 109.5 . . ?
C00I C00K H00M 120.0 . . ?
C00I C00K C00L 119.9(11) . . ?
C00L C00K H00M 120.0 . . ?
C00H C00L C00K 120.3(12) . . ?
C00H C00L H00N 119.8 . . ?
C00K C00L H00N 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I001 C005 C007 O002 3.1(13) . . . . ?
I001 C005 C007 C00B -177.7(7) . . . . ?
I001 C005 C00C C006 177.5(8) . . . . ?
O002 C007 C00B C009 179.7(9) . . . . ?
O003 C006 C009 C00B -177.1(9) . . . . ?
O003 C006 C009 C00D 3.2(15) . . . . ?
O003 C006 C00C C005 178.6(10) . . . . ?
N004 C00D C00E C008 0.5(18) . . . . ?
C005 C007 C00B C009 0.7(15) . . . . ?
C006 C009 C00B C007 -2.0(14) . . . . ?
C006 C009 C00D N004 -163.8(9) . . . . ?
C006 C009 C00D C00E 15.5(16) . . . . ?
C007 C005 C00C C006 -1.2(15) . . . . ?
C008 C00G C00I C00K 1(2) . . . . ?
C008 C00H C00L C00K 0(3) . . . . ?
C009 C006 C00C C005 -0.2(15) . . . . ?
C009 C00D C00E C008 -178.8(10) . . . . ?
C00A O002 C007 C005 176.7(10) . . . . ?
C00A O002 C007 C00B -2.4(15) . . . . ?
C00B C009 C00D N004 16.5(12) . . . . ?
C00B C009 C00D C00E -164.1(11) . . . . ?
C00C C005 C007 O002 -178.2(9) . . . . ?
C00C C005 C007 C00B 1.0(15) . . . . ?
C00C C006 C009 C00B 1.7(14) . . . . ?
C00C C006 C009 C00D -178.0(9) . . . . ?
C00D C009 C00B C007 177.7(9) . . . . ?
C00E C008 C00G C00I -178.6(12) . . . . ?
C00E C008 C00H C00L 178.7(15) . . . . ?
C00G C008 C00E C00D -29(2) . . . . ?
C00G C008 C00H C00L 2(2) . . . . ?
C00G C00I C00K C00L 2(3) . . . . ?
C00H C008 C00E C00D 155.2(12) . . . . ?
C00H C008 C00G C00I -3(2) . . . . ?
C00I C00K C00L C00H -2(3) . . . . ?
C00J O003 C006 C009 179.8(11) . . . . ?
C00J O003 C006 C00C 1.0(16) . . . . ?

_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 2.423
_oxdiff_exptl_absorpt_empirical_full_min 0.186
####################################################################### 
# 
# 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_isk-466-03-253k_auto
_database_code_depnum_ccdc_archive 'CCDC 2525258'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Seki'
;Shizuoka University
Japan
;
_audit_update_record             
;
2026-04-15 deposited with the CCDC.	2026-04-16 downloaded from the CCDC.
;
_audit_creation_date             2026-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.04.07 svn.r39635298 for OlexSys, GUI svn.r7533)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 I N O2'
_chemical_formula_sum            'C17 H14 I N O2'
_chemical_formula_weight         391.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H14INO2
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.0875(5)
_cell_length_b                   7.0639(3)
_cell_length_c                   27.7232(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3150.48(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4266
_cell_measurement_temperature    253.00(10)
_cell_measurement_theta_max      76.5210
_cell_measurement_theta_min      3.1270
_shelx_estimated_absorpt_T_max   0.740
_shelx_estimated_absorpt_T_min   0.059
_exptl_absorpt_coefficient_mu    16.002
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.088
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 0 -12 0.0207
-1 5 -2 0.2188
1 -5 2 0.2264
-7 0 -13 0.0223
7 0 13 0.0171
-8 0 12 0.0185

_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
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
7.6870 -0.1007 -12.1783 0.1378 0.3813 -0.9141
-0.7442 4.5576 -1.5720 -0.3047 -0.8685 -0.3911
0.7305 -4.5576 1.5937 0.3044 0.8678 0.3928
-7.4119 -0.0824 -12.6583 0.9032 -0.4292 0.0090
7.4119 0.0824 12.6583 -0.9032 0.4292 -0.0090
-7.7143 -0.0293 12.1330 -0.1230 -0.3594 0.9250

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9808
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_min         4.210
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      253.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  15.00   0.50    1.92    --  -47.55  66.00-159.00   52
  2  ω   -118.00 -41.00   0.50    1.92    --  -47.55 -66.00  65.00  154
  3  ω    -73.00 -43.00   0.50    7.67    -- -104.50  66.00  62.00   60
  4  ω    -76.00 -50.00   0.50    7.67    -- -104.50  66.00-159.00   52
  5  ω    -97.00 -38.00   0.50    7.67    -- -104.50  93.00 -60.00  118
  6  ω     37.00  78.00   0.50    7.67    --  107.14 -66.00  65.00   82
  7  ω    -16.00  24.00   0.50    1.92    --  -47.55  19.00-150.00   80
  8  ω    -10.00  21.00   0.50    1.92    --  -47.55  19.00   0.00   62
  9  ω    -62.00 -37.00   0.50    7.67    -- -104.50  57.00  90.00   50
 10  ω   -105.00 -59.00   0.50    7.67    -- -104.50 125.00-150.00   92
 11  ω    -62.00 -36.00   0.50    7.67    -- -104.50  57.00-180.00   52
 12  ω    -62.00 -37.00   0.50    7.67    -- -104.50  57.00 120.00   50
 13  ω     42.00  67.00   0.50    7.67    --  107.14 -57.00 120.00   50
 14  ω     37.00  63.00   0.50    7.67    --  107.14 -57.00-180.00   52
 15  ω     36.00  69.00   0.50    7.67    --  107.14 -57.00-120.00   66
 16  ω     35.00  68.00   0.50    7.67    --  107.14 -57.00-150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0494671000
_diffrn_orient_matrix_UB_12      -0.0893435000
_diffrn_orient_matrix_UB_13      -0.0418019000
_diffrn_orient_matrix_UB_21      0.0533372000
_diffrn_orient_matrix_UB_22      -0.1805115000
_diffrn_orient_matrix_UB_23      0.0038536000
_diffrn_orient_matrix_UB_31      -0.0623993000
_diffrn_orient_matrix_UB_32      -0.0834607000
_diffrn_orient_matrix_UB_33      0.0363663000
_diffrn_oxdiff_digest_hkl        
;
01e64607f0c7faff5784369e367bf05e72bceb
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2358
_reflns_number_total             2864
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.911
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.101
_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)+(0.1166P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1749
_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:
 C007(H007), C00C(H00D), C00D(H00E), C00F(H00F), C00I(H00J), C00J(H00K),
 C00K(H00L), C00L(H00M)
2.b Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C), C00H(H00G,H00H,H00I)
;
_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
I001 I 0.53596(2) 0.39799(7) 0.20988(2) 0.0449(2) Uani 1 1 d . . . . .
O002 O 0.7287(3) 0.4157(8) 0.22357(17) 0.0531(13) Uani 1 1 d . . . . .
O003 O 0.5799(3) 0.4175(8) 0.40352(16) 0.0551(13) Uani 1 1 d . . . . .
N004 N 0.8419(3) 0.4245(7) 0.39057(17) 0.0417(12) Uani 1 1 d . . . . .
C005 C 0.6089(4) 0.4098(8) 0.2725(2) 0.0380(13) Uani 1 1 d . . . . .
C006 C 0.6171(4) 0.4213(8) 0.3592(2) 0.0375(13) Uani 1 1 d . . . . .
C007 C 0.5705(4) 0.4088(9) 0.3166(2) 0.0400(13) Uani 1 1 d . . . . .
H007 H 0.512318 0.399694 0.318360 0.048 Uiso 1 1 calc R U . . .
C008 C 0.6952(4) 0.4202(9) 0.2688(2) 0.0415(14) Uani 1 1 d . . . . .
C009 C 0.7577(4) 0.4619(9) 0.40005(19) 0.0396(13) Uani 1 1 d . . . . .
C00A C 0.8167(5) 0.4125(12) 0.2192(3) 0.0521(18) Uani 1 1 d . . . . .
H00A H 0.831773 0.402027 0.185386 0.078 Uiso 1 1 calc R U . . .
H00B H 0.838723 0.304775 0.236711 0.078 Uiso 1 1 calc R U . . .
H00C H 0.839667 0.528355 0.232370 0.078 Uiso 1 1 calc R U . . .
C00B C 0.7044(4) 0.4398(8) 0.3567(2) 0.0368(13) Uani 1 1 d . . . . .
C00C C 0.7406(4) 0.4355(9) 0.3111(2) 0.0396(13) Uani 1 1 d . . . . .
H00D H 0.798761 0.443381 0.308921 0.047 Uiso 1 1 calc R U . . .
C00D C 0.7338(4) 0.5130(10) 0.4445(2) 0.0431(13) Uani 1 1 d . . . . .
H00E H 0.676790 0.538538 0.448058 0.052 Uiso 1 1 calc R U . . .
C00E C 0.7840(4) 0.5348(10) 0.4887(2) 0.0454(14) Uani 1 1 d . . . . .
C00F C 0.8675(5) 0.5805(12) 0.4899(3) 0.060(2) Uani 1 1 d . . . . .
H00F H 0.896972 0.598102 0.460979 0.072 Uiso 1 1 calc R U . . .
C00G C 0.9088(4) 0.3931(13) 0.3811(2) 0.060(2) Uani 1 1 d . . . . .
C00H C 0.4924(5) 0.4003(14) 0.4064(3) 0.072(3) Uani 1 1 d . . . . .
H00G H 0.466635 0.498532 0.387032 0.108 Uiso 1 1 calc R U . . .
H00H H 0.474944 0.413569 0.439688 0.108 Uiso 1 1 calc R U . . .
H00I H 0.475726 0.277107 0.394352 0.108 Uiso 1 1 calc R U . . .
C00I C 0.7419(6) 0.5111(14) 0.5324(3) 0.073(2) Uani 1 1 d . . . . .
H00J H 0.685004 0.481250 0.532429 0.088 Uiso 1 1 calc R U . . .
C00J C 0.8680(8) 0.5763(15) 0.5758(3) 0.087(3) Uani 1 1 d . . . . .
H00K H 0.896581 0.589657 0.605182 0.105 Uiso 1 1 calc R U . . .
C00K C 0.9079(6) 0.6004(14) 0.5342(3) 0.078(3) Uani 1 1 d . . . . .
H00L H 0.964738 0.631547 0.534613 0.093 Uiso 1 1 calc R U . . .
C00L C 0.7842(8) 0.5315(17) 0.5757(3) 0.092(3) Uani 1 1 d . . . . .
H00M H 0.755852 0.514931 0.604999 0.110 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
I001 C005 2.097(6) . ?
O002 C008 1.365(8) . ?
O002 C00A 1.421(8) . ?
O003 C006 1.368(7) . ?
O003 C00H 1.415(10) . ?
N004 C009 1.404(8) . ?
N004 C00G 1.131(8) . ?
C005 C007 1.370(10) . ?
C005 C008 1.394(9) . ?
C006 C007 1.400(9) . ?
C006 C00B 1.412(8) . ?
C007 H007 0.9400 . ?
C008 C00C 1.387(9) . ?
C009 C00B 1.485(8) . ?
C009 C00D 1.341(8) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A H00C 0.9700 . ?
C00B C00C 1.391(8) . ?
C00C H00D 0.9400 . ?
C00D H00E 0.9400 . ?
C00D C00E 1.475(8) . ?
C00E C00F 1.382(10) . ?
C00E C00I 1.397(10) . ?
C00F H00F 0.9400 . ?
C00F C00K 1.396(10) . ?
C00H H00G 0.9700 . ?
C00H H00H 0.9700 . ?
C00H H00I 0.9700 . ?
C00I H00J 0.9400 . ?
C00I C00L 1.386(12) . ?
C00J H00K 0.9400 . ?
C00J C00K 1.332(15) . ?
C00J C00L 1.385(15) . ?
C00K H00L 0.9400 . ?
C00L H00M 0.9400 . ?

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
C008 O002 C00A 118.3(6) . . ?
C006 O003 C00H 119.1(5) . . ?
C00G N004 C009 177.3(6) . . ?
C007 C005 I001 119.1(5) . . ?
C007 C005 C008 121.0(6) . . ?
C008 C005 I001 119.9(5) . . ?
O003 C006 C007 121.5(5) . . ?
O003 C006 C00B 118.7(5) . . ?
C007 C006 C00B 119.8(5) . . ?
C005 C007 C006 120.7(6) . . ?
C005 C007 H007 119.6 . . ?
C006 C007 H007 119.6 . . ?
O002 C008 C005 117.5(6) . . ?
O002 C008 C00C 124.8(6) . . ?
C00C C008 C005 117.7(6) . . ?
N004 C009 C00B 112.7(5) . . ?
C00D C009 N004 120.0(5) . . ?
C00D C009 C00B 127.3(6) . . ?
O002 C00A H00A 109.5 . . ?
O002 C00A H00B 109.5 . . ?
O002 C00A H00C 109.5 . . ?
H00A C00A H00B 109.5 . . ?
H00A C00A H00C 109.5 . . ?
H00B C00A H00C 109.5 . . ?
C006 C00B C009 123.0(5) . . ?
C00C C00B C006 117.2(5) . . ?
C00C C00B C009 119.7(5) . . ?
C008 C00C C00B 123.4(6) . . ?
C008 C00C H00D 118.3 . . ?
C00B C00C H00D 118.3 . . ?
C009 C00D H00E 115.3 . . ?
C009 C00D C00E 129.4(6) . . ?
C00E C00D H00E 115.3 . . ?
C00F C00E C00D 125.2(6) . . ?
C00F C00E C00I 118.6(6) . . ?
C00I C00E C00D 116.2(7) . . ?
C00E C00F H00F 120.1 . . ?
C00E C00F C00K 119.8(8) . . ?
C00K C00F H00F 120.1 . . ?
O003 C00H H00G 109.5 . . ?
O003 C00H H00H 109.5 . . ?
O003 C00H H00I 109.5 . . ?
H00G C00H H00H 109.5 . . ?
H00G C00H H00I 109.5 . . ?
H00H C00H H00I 109.5 . . ?
C00E C00I H00J 120.0 . . ?
C00L C00I C00E 120.0(9) . . ?
C00L C00I H00J 120.0 . . ?
C00K C00J H00K 120.1 . . ?
C00K C00J C00L 119.8(8) . . ?
C00L C00J H00K 120.1 . . ?
C00F C00K H00L 119.2 . . ?
C00J C00K C00F 121.6(10) . . ?
C00J C00K H00L 119.2 . . ?
C00I C00L H00M 119.9 . . ?
C00J C00L C00I 120.3(8) . . ?
C00J C00L H00M 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I001 C005 C007 C006 -178.4(5) . . . . ?
I001 C005 C008 O002 -2.2(8) . . . . ?
I001 C005 C008 C00C 177.4(5) . . . . ?
O002 C008 C00C C00B 180.0(6) . . . . ?
O003 C006 C007 C005 -178.9(6) . . . . ?
O003 C006 C00B C009 -2.2(9) . . . . ?
O003 C006 C00B C00C 177.5(6) . . . . ?
N004 C009 C00B C006 163.1(5) . . . . ?
N004 C009 C00B C00C -16.5(8) . . . . ?
N004 C009 C00D C00E -1.4(11) . . . . ?
C005 C008 C00C C00B 0.4(10) . . . . ?
C006 C00B C00C C008 2.1(10) . . . . ?
C007 C005 C008 O002 178.4(6) . . . . ?
C007 C005 C008 C00C -2.0(9) . . . . ?
C007 C006 C00B C009 177.4(6) . . . . ?
C007 C006 C00B C00C -3.0(9) . . . . ?
C008 C005 C007 C006 1.0(9) . . . . ?
C009 C00B C00C C008 -178.3(6) . . . . ?
C009 C00D C00E C00F 27.6(13) . . . . ?
C009 C00D C00E C00I -154.0(8) . . . . ?
C00A O002 C008 C005 -175.6(6) . . . . ?
C00A O002 C008 C00C 4.8(9) . . . . ?
C00B C006 C007 C005 1.6(9) . . . . ?
C00B C009 C00D C00E 179.2(7) . . . . ?
C00D C009 C00B C006 -17.4(10) . . . . ?
C00D C009 C00B C00C 163.0(7) . . . . ?
C00D C00E C00F C00K 178.9(8) . . . . ?
C00D C00E C00I C00L -179.2(9) . . . . ?
C00E C00F C00K C00J 0.0(14) . . . . ?
C00E C00I C00L C00J 0.3(17) . . . . ?
C00F C00E C00I C00L -0.7(14) . . . . ?
C00H O003 C006 C007 0.1(9) . . . . ?
C00H O003 C006 C00B 179.6(6) . . . . ?
C00I C00E C00F C00K 0.5(12) . . . . ?
C00K C00J C00L C00I 0.2(18) . . . . ?
C00L C00J C00K C00F -0.4(16) . . . . ?

_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 3.272
_oxdiff_exptl_absorpt_empirical_full_min 0.201
####################################################################### 
# 
# 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_isk-466-05-173k_autored
_database_code_depnum_ccdc_archive 'CCDC 2525260'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Seki'
;Shizuoka University
Japan
;
_audit_update_record             
;
2026-04-15 deposited with the CCDC.	2026-04-16 downloaded from the CCDC.
;
_audit_creation_date             2026-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.04.07 svn.r39635298 for OlexSys, GUI svn.r7533)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 I N O2'
_chemical_formula_sum            'C17 H14 I N O2'
_chemical_formula_weight         391.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H14INO2
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.0629(5)
_cell_length_b                   7.0075(2)
_cell_length_c                   27.6441(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3111.65(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4603
_cell_measurement_temperature    173.02(10)
_cell_measurement_theta_max      75.9500
_cell_measurement_theta_min      4.2670
_shelx_estimated_absorpt_T_max   0.738
_shelx_estimated_absorpt_T_min   0.058
_exptl_absorpt_coefficient_mu    16.202
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.105
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-8 0 -11 0.0223
8 0 11 0.0207
5 0 -15 0.0155
-5 0 16 0.0138
-8 0 -11 0.0192
0 -5 0 0.2147
0 5 0 0.2139

_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
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
-8.1277 0.1097 -11.2351 -0.0878 -0.3831 0.9195
8.1155 0.0348 11.2696 0.0946 0.4114 -0.9065
5.2676 0.1000 -15.4763 -0.9844 0.1286 0.1197
-5.1545 -0.1260 15.5855 0.9827 -0.1284 -0.1333
-8.3562 -0.1230 -10.7269 -0.0598 -0.4349 0.8985
-0.1066 -4.5463 0.4916 -0.1155 -0.8988 -0.4229
0.1670 4.5465 -0.4140 0.1159 0.9018 0.4163

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10322
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.230
_diffrn_reflns_theta_min         3.197
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.02(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  60.00   0.50    0.64    --  107.14 -57.00-120.00   50
  2  ω     35.00  69.00   0.50    0.64    --  107.14 -57.00 -90.00   68
  3  ω     37.00  63.00   0.50    0.64    --  107.14 -57.00 -60.00   52
  4  ω     72.00 118.00   0.50    0.16    --   47.18  58.00-147.00   92
  5  ω    100.00 176.00   0.50    0.64    --  107.14  58.00-147.00  152
  6  ω    -20.00  45.00   0.50    0.16    --   47.18 -38.00 -60.00  130
  7  ω     39.00  64.00   0.50    0.64    --  107.14 -57.00-150.00   50
  8  ω     36.00 105.00   0.50    0.64    --  107.14 -90.00-156.00  138
  9  ω     -3.00  27.00   0.50    0.16    --  -47.18  19.00-150.00   60
 10  ω    -22.00  14.00   0.50    0.16    --  -47.18  19.00 -60.00   72
 11  ω    -15.00  27.00   0.50    0.16    --  -47.18  19.00 -30.00   84
 12  ω    -78.00 -44.00   0.50    0.64    -- -104.50  76.00  71.00   68
 13  ω    -61.00 -32.00   0.50    0.64    -- -104.50  57.00  60.00   58
 14  ω    -59.00 -33.00   0.50    0.64    -- -104.50  57.00  30.00   52
 15  ω    -62.00 -33.00   0.50    0.64    -- -104.50  57.00-120.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0523518000
_diffrn_orient_matrix_UB_12      0.0316092000
_diffrn_orient_matrix_UB_13      0.0459953000
_diffrn_orient_matrix_UB_21      0.0404800000
_diffrn_orient_matrix_UB_22      0.1974800000
_diffrn_orient_matrix_UB_23      0.0067437000
_diffrn_orient_matrix_UB_31      -0.0693832000
_diffrn_orient_matrix_UB_32      0.0913125000
_diffrn_orient_matrix_UB_33      -0.0307590000
_diffrn_oxdiff_digest_hkl        
;
01b58925e015115ae0587f10fdd36be97de0e8
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2317
_reflns_number_total             2834
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.788
_refine_diff_density_min         -1.446
_refine_diff_density_rms         0.195
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.045
_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)+(0.1080P)²+1.8223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1591
_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. Restrained distances
 C00K-C00H
 1.39 with sigma of 0.02
 C00K-C00L
 1.39 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C00F \\sim C00G \\sim C00H \\sim C00J \\sim C00K \\sim C00L: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00J(H00K),
 C00K(H00L), C00L(H00M)
4.b Idealised Me refined as rotating group:
 C007(H00A,H00B,H00C), C00I(H00F,H00I,H00J)
;
_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
I001 I 0.53516(2) 0.60741(5) 0.21010(2) 0.0326(2) Uani 1 1 d . . . . .
O002 O 0.5801(3) 0.5836(6) 0.40444(15) 0.0392(10) Uani 1 1 d . . . . .
O003 O 0.7279(3) 0.5932(6) 0.22336(17) 0.0361(9) Uani 1 1 d . . . . .
N004 N 0.8425(3) 0.5802(6) 0.39081(18) 0.0331(10) Uani 1 1 d . . . . .
C005 C 0.6084(3) 0.5964(7) 0.2723(2) 0.0281(11) Uani 1 1 d . . . . .
C006 C 0.6173(3) 0.5813(7) 0.3591(2) 0.0288(11) Uani 1 1 d . . . . .
C007 C 0.8162(4) 0.5969(9) 0.2196(3) 0.0390(14) Uani 1 1 d . . . . .
H00A H 0.832299 0.608283 0.185564 0.059 Uiso 1 1 calc R U . . .
H00B H 0.839261 0.478714 0.233064 0.059 Uiso 1 1 calc R U . . .
H00C H 0.838015 0.706321 0.237744 0.059 Uiso 1 1 calc R U . . .
C008 C 0.7041(4) 0.5671(8) 0.3573(2) 0.0308(11) Uani 1 1 d . . . . .
C009 C 0.5701(4) 0.5954(7) 0.3170(2) 0.0343(12) Uani 1 1 d . . . . .
H009 H 0.511202 0.604280 0.319084 0.041 Uiso 1 1 calc R U . . .
C00A C 0.7580(3) 0.5424(8) 0.40000(19) 0.0308(11) Uani 1 1 d . . . . .
C00B C 0.9111(4) 0.6099(10) 0.3811(2) 0.0448(15) Uani 1 1 d . . . . .
C00C C 0.7345(3) 0.4923(8) 0.4448(2) 0.0354(12) Uani 1 1 d . . . . .
H00D H 0.676785 0.466086 0.448464 0.043 Uiso 1 1 calc R U . . .
C00D C 0.6942(4) 0.5877(7) 0.2692(2) 0.0303(12) Uani 1 1 d . . . . .
C00E C 0.7411(4) 0.5705(8) 0.3111(2) 0.0335(12) Uani 1 1 d . . . . .
H00E H 0.799971 0.560844 0.308530 0.040 Uiso 1 1 calc R U . . .
C00F C 0.7848(4) 0.4718(8) 0.4892(2) 0.0369(13) Uani 1 1 d . U . . .
C00G C 0.8686(4) 0.4177(9) 0.4897(3) 0.0447(15) Uani 1 1 d . U . . .
H00G H 0.896897 0.394996 0.460121 0.054 Uiso 1 1 calc R U . . .
C00H C 0.9110(5) 0.3969(10) 0.5334(3) 0.056(2) Uani 1 1 d D U . . .
H00H H 0.968347 0.363480 0.533405 0.067 Uiso 1 1 calc R U . . .
C00I C 0.4915(4) 0.5997(12) 0.4071(3) 0.0517(18) Uani 1 1 d . . . . .
H00F H 0.473512 0.714911 0.389915 0.078 Uiso 1 1 calc R U . . .
H00I H 0.474314 0.607677 0.441025 0.078 Uiso 1 1 calc R U . . .
H00J H 0.465871 0.487369 0.392064 0.078 Uiso 1 1 calc R U . . .
C00J C 0.7442(5) 0.4966(10) 0.5331(2) 0.0518(16) Uani 1 1 d . U . . .
H00K H 0.686554 0.526435 0.533456 0.062 Uiso 1 1 calc R U . . .
C00K C 0.8702(5) 0.4247(12) 0.5766(3) 0.065(2) Uani 1 1 d D U . . .
H00L H 0.898840 0.406964 0.606328 0.078 Uiso 1 1 calc R U . . .
C00L C 0.7875(6) 0.4782(12) 0.5767(3) 0.066(2) Uani 1 1 d D U . . .
H00M H 0.759994 0.502517 0.606490 0.079 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
I001 C005 2.086(5) . ?
O002 C006 1.388(7) . ?
O002 C00I 1.430(9) . ?
O003 C007 1.423(8) . ?
O003 C00D 1.379(8) . ?
N004 C00A 1.405(7) . ?
N004 C00B 1.154(8) . ?
C005 C009 1.381(10) . ?
C005 C00D 1.382(8) . ?
C006 C008 1.400(8) . ?
C006 C009 1.391(9) . ?
C007 H00A 0.9800 . ?
C007 H00B 0.9800 . ?
C007 H00C 0.9800 . ?
C008 C00A 1.474(8) . ?
C008 C00E 1.410(8) . ?
C009 H009 0.9500 . ?
C00A C00C 1.341(8) . ?
C00C H00D 0.9500 . ?
C00C C00F 1.477(8) . ?
C00D C00E 1.387(9) . ?
C00E H00E 0.9500 . ?
C00F C00G 1.398(9) . ?
C00F C00J 1.388(9) . ?
C00G H00G 0.9500 . ?
C00G C00H 1.394(10) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.376(11) . ?
C00I H00F 0.9800 . ?
C00I H00I 0.9800 . ?
C00I H00J 0.9800 . ?
C00J H00K 0.9500 . ?
C00J C00L 1.399(10) . ?
C00K H00L 0.9500 . ?
C00K C00L 1.379(11) . ?
C00L H00M 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
C006 O002 C00I 118.4(4) . . ?
C00D O003 C007 117.3(5) . . ?
C00B N004 C00A 176.9(6) . . ?
C009 C005 I001 119.1(4) . . ?
C009 C005 C00D 120.0(6) . . ?
C00D C005 I001 120.9(4) . . ?
O002 C006 C008 117.5(5) . . ?
O002 C006 C009 121.3(5) . . ?
C009 C006 C008 121.2(5) . . ?
O003 C007 H00A 109.5 . . ?
O003 C007 H00B 109.5 . . ?
O003 C007 H00C 109.5 . . ?
H00A C007 H00B 109.5 . . ?
H00A C007 H00C 109.5 . . ?
H00B C007 H00C 109.5 . . ?
C006 C008 C00A 124.4(5) . . ?
C006 C008 C00E 116.8(5) . . ?
C00E C008 C00A 118.7(5) . . ?
C005 C009 C006 120.4(5) . . ?
C005 C009 H009 119.8 . . ?
C006 C009 H009 119.8 . . ?
N004 C00A C008 113.6(5) . . ?
C00C C00A N004 119.3(5) . . ?
C00C C00A C008 127.1(5) . . ?
C00A C00C H00D 115.2 . . ?
C00A C00C C00F 129.6(5) . . ?
C00F C00C H00D 115.2 . . ?
O003 C00D C005 116.6(5) . . ?
O003 C00D C00E 123.8(6) . . ?
C005 C00D C00E 119.6(6) . . ?
C008 C00E H00E 119.0 . . ?
C00D C00E C008 121.9(6) . . ?
C00D C00E H00E 119.0 . . ?
C00G C00F C00C 124.3(6) . . ?
C00J C00F C00C 117.2(6) . . ?
C00J C00F C00G 118.4(6) . . ?
C00F C00G H00G 119.7 . . ?
C00H C00G C00F 120.6(7) . . ?
C00H C00G H00G 119.7 . . ?
C00G C00H H00H 119.9 . . ?
C00K C00H C00G 120.2(7) . . ?
C00K C00H H00H 119.9 . . ?
O002 C00I H00F 109.5 . . ?
O002 C00I H00I 109.5 . . ?
O002 C00I H00J 109.5 . . ?
H00F C00I H00I 109.5 . . ?
H00F C00I H00J 109.5 . . ?
H00I C00I H00J 109.5 . . ?
C00F C00J H00K 119.7 . . ?
C00F C00J C00L 120.6(7) . . ?
C00L C00J H00K 119.7 . . ?
C00H C00K H00L 120.0 . . ?
C00H C00K C00L 120.0(7) . . ?
C00L C00K H00L 120.0 . . ?
C00J C00L H00M 119.9 . . ?
C00K C00L C00J 120.1(7) . . ?
C00K C00L H00M 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I001 C005 C009 C006 177.7(4) . . . . ?
I001 C005 C00D O003 2.1(6) . . . . ?
I001 C005 C00D C00E -176.7(4) . . . . ?
O002 C006 C008 C00A 4.0(8) . . . . ?
O002 C006 C008 C00E -178.2(5) . . . . ?
O002 C006 C009 C005 178.8(5) . . . . ?
O003 C00D C00E C008 179.4(5) . . . . ?
N004 C00A C00C C00F 1.3(9) . . . . ?
C005 C00D C00E C008 -1.8(9) . . . . ?
C006 C008 C00A N004 -164.7(5) . . . . ?
C006 C008 C00A C00C 14.3(9) . . . . ?
C006 C008 C00E C00D 0.2(9) . . . . ?
C007 O003 C00D C005 176.0(5) . . . . ?
C007 O003 C00D C00E -5.2(8) . . . . ?
C008 C006 C009 C005 -0.3(8) . . . . ?
C008 C00A C00C C00F -177.7(6) . . . . ?
C009 C005 C00D O003 -178.7(4) . . . . ?
C009 C005 C00D C00E 2.4(8) . . . . ?
C009 C006 C008 C00A -176.9(5) . . . . ?
C009 C006 C008 C00E 0.9(8) . . . . ?
C00A C008 C00E C00D 178.1(5) . . . . ?
C00A C00C C00F C00G -30.3(10) . . . . ?
C00A C00C C00F C00J 153.8(6) . . . . ?
C00C C00F C00G C00H -178.3(6) . . . . ?
C00C C00F C00J C00L 179.6(7) . . . . ?
C00D C005 C009 C006 -1.4(8) . . . . ?
C00E C008 C00A N004 17.6(7) . . . . ?
C00E C008 C00A C00C -163.4(6) . . . . ?
C00F C00G C00H C00K 1.7(11) . . . . ?
C00F C00J C00L C00K -3.6(12) . . . . ?
C00G C00F C00J C00L 3.5(10) . . . . ?
C00G C00H C00K C00L -1.7(12) . . . . ?
C00H C00K C00L C00J 2.6(13) . . . . ?
C00I O002 C006 C008 179.5(5) . . . . ?
C00I O002 C006 C009 0.4(8) . . . . ?
C00J C00F C00G C00H -2.5(10) . . . . ?

_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 2.182
_oxdiff_exptl_absorpt_empirical_full_min 0.421
####################################################################### 
# 
# 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_isk-466-02-273k_auto
_database_code_depnum_ccdc_archive 'CCDC 2525257'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Seki'
;Shizuoka University
Japan
;
_audit_update_record             
;
2026-04-15 deposited with the CCDC.	2026-04-16 downloaded from the CCDC.
;
_audit_creation_date             2026-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.04.07 svn.r39635298 for OlexSys, GUI svn.r7533)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 I N O2'
_chemical_formula_sum            'C17 H14 I N O2'
_chemical_formula_weight         391.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H14INO2
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.0841(4)
_cell_length_b                   7.0891(2)
_cell_length_c                   27.7472(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3163.79(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4388
_cell_measurement_temperature    273.00(10)
_cell_measurement_theta_max      75.8250
_cell_measurement_theta_min      4.1680
_shelx_estimated_absorpt_T_max   0.741
_shelx_estimated_absorpt_T_min   0.059
_exptl_absorpt_coefficient_mu    15.935
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.076
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 0 14 0.0131
7 0 -14 0.0185
-2 -5 -2 0.2210
1 5 2 0.2212
7 0 13 0.0206
-7 0 -13 0.0206

_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
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
-6.7948 0.0648 13.6690 -0.2417 -0.3216 0.9155
6.8297 0.0456 -13.6182 0.2280 0.3038 -0.9251
-1.5831 -4.5250 -1.7800 0.5550 0.7229 0.4116
1.4656 4.5262 2.0166 -0.5592 -0.7285 -0.3957
7.2959 0.0474 12.8858 -0.9031 0.4292 0.0093
-7.2959 -0.0474 -12.8858 0.9031 -0.4292 -0.0093

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9790
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.185
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      273.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  66.00   0.50    2.01    --   47.43 -66.00  65.00  170
  2  ω    -57.00 -32.00   0.50    8.06    -- -104.50  66.00  62.00   50
  3  ω     35.00  61.00   0.50    8.06    --  107.14 -66.00 -72.00   52
  4  ω     42.00  70.00   0.50    8.06    --  107.14 -66.00  65.00   56
  5  ω     90.00 173.00   0.50    8.06    --  107.14  93.00 -60.00  166
  6  ω    -22.00  27.00   0.50    2.01    --  -47.43  19.00-150.00   98
  7  ω     20.00  71.00   0.50    2.01    --   47.43-125.00  30.00  102
  8  ω   -168.00 -94.00   0.50    8.06    -- -104.50 -99.00-120.00  148
  9  ω    -60.00 -35.00   0.50    8.06    -- -104.50  57.00-120.00   50
 10  ω     35.00  62.00   0.50    8.06    --  107.14 -57.00  30.00   54
 11  ω     36.00  69.00   0.50    8.06    --  107.14 -57.00-120.00   66
 12  ω     36.00  69.00   0.50    8.06    --  107.14 -57.00-150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0493782000
_diffrn_orient_matrix_UB_12      -0.0889354000
_diffrn_orient_matrix_UB_13      -0.0418039000
_diffrn_orient_matrix_UB_21      0.0532735000
_diffrn_orient_matrix_UB_22      -0.1798928000
_diffrn_orient_matrix_UB_23      0.0038083000
_diffrn_orient_matrix_UB_31      -0.0623956000
_diffrn_orient_matrix_UB_32      -0.0834228000
_diffrn_orient_matrix_UB_33      0.0363567000
_diffrn_oxdiff_digest_hkl        
;
01ca09cbe3e72923a41c5b3d7e263dcfd33cd9
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2417
_reflns_number_total             2893
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.292
_refine_diff_density_min         -0.979
_refine_diff_density_rms         0.224
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1499P)²+1.2034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1989
_refine_ls_wR_factor_ref         0.2083
_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. Restrained distances
 C00K-C00J
 1.39 with sigma of 0.02
 C00F-C00E
 1.39 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C00E \\sim C00F \\sim C00I \\sim C00J \\sim C00K \\sim C00L: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00D(H00E), C00E(H00F), C00I(H00J), C00J(H00K),
 C00K(H00L), C00L(H00M)
4.b Idealised Me refined as rotating group:
 C00C(H00A,H00C,H00D), C00H(H00G,H00H,H00I)
;
_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
I001 I 0.46383(3) 0.40040(7) 0.20987(2) 0.0476(3) Uani 1 1 d . . . . .
O1 O 0.4200(3) 0.4201(8) 0.40317(19) 0.0590(14) Uani 1 1 d . . . . .
O003 O 0.2712(3) 0.4206(8) 0.2240(2) 0.0574(14) Uani 1 1 d . . . . .
N004 N 0.1581(4) 0.4274(7) 0.3906(2) 0.0462(13) Uani 1 1 d . . . . .
C005 C 0.3845(4) 0.4239(9) 0.3592(3) 0.0435(14) Uani 1 1 d . . . . .
C006 C 0.3042(5) 0.4253(8) 0.2683(2) 0.0430(14) Uani 1 1 d . . . . .
C007 C 0.3918(4) 0.4113(8) 0.2724(3) 0.0392(14) Uani 1 1 d . . . . .
C008 C 0.4297(4) 0.4111(8) 0.3161(2) 0.0408(13) Uani 1 1 d . . . . .
H008 H 0.487323 0.402334 0.317476 0.049 Uiso 1 1 calc R U . . .
C009 C 0.2422(4) 0.4632(9) 0.3999(2) 0.0390(12) Uani 1 1 d . . . . .
C00A C 0.2959(4) 0.4415(8) 0.3566(2) 0.0395(13) Uani 1 1 d . . . . .
C00B C 0.2593(4) 0.4377(8) 0.3116(2) 0.0392(13) Uani 1 1 d . . . . .
H00B H 0.201648 0.443636 0.309794 0.047 Uiso 1 1 calc R U . . .
C00C C 0.1828(6) 0.4157(13) 0.2190(3) 0.063(2) Uani 1 1 d . . . . .
H00A H 0.168725 0.389072 0.186050 0.094 Uiso 1 1 calc R U . . .
H00C H 0.159995 0.535600 0.228062 0.094 Uiso 1 1 calc R U . . .
H00D H 0.160431 0.318978 0.239419 0.094 Uiso 1 1 calc R U . . .
C00D C 0.2660(4) 0.5130(9) 0.4445(2) 0.0465(14) Uani 1 1 d . . . . .
H00E H 0.322539 0.536556 0.447962 0.056 Uiso 1 1 calc R U . . .
C00E C 0.1321(5) 0.5825(11) 0.4898(3) 0.065(2) Uani 1 1 d D U . . .
H00F H 0.103060 0.600752 0.461174 0.078 Uiso 1 1 calc R U . . .
C00F C 0.2166(4) 0.5361(9) 0.4886(2) 0.0505(15) Uani 1 1 d D U . . .
C00G C 0.0900(5) 0.3950(12) 0.3809(3) 0.064(2) Uani 1 1 d . . . . .
C00H C 0.5083(5) 0.4021(16) 0.4059(4) 0.083(3) Uani 1 1 d . . . . .
H00G H 0.525452 0.289898 0.389306 0.124 Uiso 1 1 calc R U . . .
H00H H 0.524926 0.394262 0.439116 0.124 Uiso 1 1 calc R U . . .
H00I H 0.533972 0.510056 0.391268 0.124 Uiso 1 1 calc R U . . .
C00I C 0.2588(6) 0.5140(14) 0.5321(3) 0.077(3) Uani 1 1 d . U . . .
H00J H 0.315220 0.485196 0.531899 0.092 Uiso 1 1 calc R U . . .
C00J C 0.1339(9) 0.5760(16) 0.5761(4) 0.097(4) Uani 1 1 d D U . . .
H00K H 0.105982 0.586776 0.605334 0.116 Uiso 1 1 calc R U . . .
C00K C 0.0916(7) 0.6014(14) 0.5339(4) 0.084(3) Uani 1 1 d D U . . .
H00L H 0.035304 0.631481 0.534648 0.101 Uiso 1 1 calc R U . . .
C00L C 0.2177(9) 0.5345(17) 0.5757(3) 0.096(3) Uani 1 1 d . U . . .
H00M H 0.246509 0.520311 0.604532 0.116 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
I001 C007 2.087(7) . ?
O1 C005 1.347(9) . ?
O1 C00H 1.428(11) . ?
O003 C006 1.338(10) . ?
O003 C00C 1.429(11) . ?
N004 C009 1.401(8) . ?
N004 C00G 1.150(10) . ?
C005 C008 1.404(10) . ?
C005 C00A 1.432(9) . ?
C006 C007 1.416(10) . ?
C006 C00B 1.404(10) . ?
C007 C008 1.357(11) . ?
C008 H008 0.9300 . ?
C009 C00A 1.486(9) . ?
C009 C00D 1.343(9) . ?
C00A C00B 1.383(9) . ?
C00B H00B 0.9300 . ?
C00C H00A 0.9600 . ?
C00C H00C 0.9600 . ?
C00C H00D 0.9600 . ?
C00D H00E 0.9300 . ?
C00D C00F 1.468(9) . ?
C00E H00F 0.9300 . ?
C00E C00F 1.399(10) . ?
C00E C00K 1.394(12) . ?
C00F C00I 1.394(11) . ?
C00H H00G 0.9600 . ?
C00H H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00I H00J 0.9300 . ?
C00I C00L 1.386(14) . ?
C00J H00K 0.9300 . ?
C00J C00K 1.366(14) . ?
C00J C00L 1.380(17) . ?
C00K H00L 0.9300 . ?
C00L H00M 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C005 O1 C00H 118.2(6) . . ?
C006 O003 C00C 119.0(7) . . ?
C00G N004 C009 176.9(7) . . ?
O1 C005 C008 123.4(6) . . ?
O1 C005 C00A 118.0(6) . . ?
C008 C005 C00A 118.6(6) . . ?
O003 C006 C007 117.8(7) . . ?
O003 C006 C00B 125.6(7) . . ?
C00B C006 C007 116.6(7) . . ?
C006 C007 I001 119.2(5) . . ?
C008 C007 I001 119.5(5) . . ?
C008 C007 C006 121.2(6) . . ?
C005 C008 H008 119.0 . . ?
C007 C008 C005 121.9(6) . . ?
C007 C008 H008 119.0 . . ?
N004 C009 C00A 113.2(5) . . ?
C00D C009 N004 119.5(6) . . ?
C00D C009 C00A 127.3(6) . . ?
C005 C00A C009 123.2(6) . . ?
C00B C00A C005 117.8(6) . . ?
C00B C00A C009 119.0(6) . . ?
C006 C00B H00B 118.1 . . ?
C00A C00B C006 123.8(6) . . ?
C00A C00B H00B 118.1 . . ?
O003 C00C H00A 109.5 . . ?
O003 C00C H00C 109.5 . . ?
O003 C00C H00D 109.5 . . ?
H00A C00C H00C 109.5 . . ?
H00A C00C H00D 109.5 . . ?
H00C C00C H00D 109.5 . . ?
C009 C00D H00E 115.0 . . ?
C009 C00D C00F 130.1(6) . . ?
C00F C00D H00E 115.0 . . ?
C00F C00E H00F 120.1 . . ?
C00K C00E H00F 120.1 . . ?
C00K C00E C00F 119.9(9) . . ?
C00E C00F C00D 124.8(7) . . ?
C00I C00F C00D 116.6(7) . . ?
C00I C00F C00E 118.6(7) . . ?
O1 C00H H00G 109.5 . . ?
O1 C00H H00H 109.5 . . ?
O1 C00H H00I 109.5 . . ?
H00G C00H H00H 109.5 . . ?
H00G C00H H00I 109.5 . . ?
H00H C00H H00I 109.5 . . ?
C00F C00I H00J 119.6 . . ?
C00L C00I C00F 120.8(9) . . ?
C00L C00I H00J 119.6 . . ?
C00K C00J H00K 119.7 . . ?
C00K C00J C00L 120.5(10) . . ?
C00L C00J H00K 119.7 . . ?
C00E C00K H00L 119.8 . . ?
C00J C00K C00E 120.5(10) . . ?
C00J C00K H00L 119.8 . . ?
C00I C00L H00M 120.1 . . ?
C00J C00L C00I 119.7(10) . . ?
C00J C00L H00M 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I001 C007 C008 C005 178.1(4) . . . . ?
O1 C005 C008 C007 178.5(6) . . . . ?
O1 C005 C00A C009 2.5(9) . . . . ?
O1 C005 C00A C00B -177.4(6) . . . . ?
O003 C006 C007 I001 3.5(7) . . . . ?
O003 C006 C007 C008 -178.7(5) . . . . ?
O003 C006 C00B C00A 179.8(6) . . . . ?
N004 C009 C00A C005 -163.8(5) . . . . ?
N004 C009 C00A C00B 16.1(8) . . . . ?
N004 C009 C00D C00F 1.0(10) . . . . ?
C005 C00A C00B C006 -2.7(9) . . . . ?
C006 C007 C008 C005 0.3(9) . . . . ?
C007 C006 C00B C00A 1.7(9) . . . . ?
C008 C005 C00A C009 -177.7(5) . . . . ?
C008 C005 C00A C00B 2.5(8) . . . . ?
C009 C00A C00B C006 177.4(5) . . . . ?
C009 C00D C00F C00E -26.7(11) . . . . ?
C009 C00D C00F C00I 154.9(8) . . . . ?
C00A C005 C008 C007 -1.3(9) . . . . ?
C00A C009 C00D C00F -179.7(6) . . . . ?
C00B C006 C007 I001 -178.2(4) . . . . ?
C00B C006 C007 C008 -0.4(8) . . . . ?
C00C O003 C006 C007 173.9(6) . . . . ?
C00C O003 C006 C00B -4.2(9) . . . . ?
C00D C009 C00A C005 16.8(10) . . . . ?
C00D C009 C00A C00B -163.4(6) . . . . ?
C00D C00F C00I C00L 179.5(10) . . . . ?
C00E C00F C00I C00L 1.1(14) . . . . ?
C00F C00E C00K C00J 0.4(13) . . . . ?
C00F C00I C00L C00J 0.4(18) . . . . ?
C00H O1 C005 C008 0.0(9) . . . . ?
C00H O1 C005 C00A 179.9(6) . . . . ?
C00K C00E C00F C00D -179.8(8) . . . . ?
C00K C00E C00F C00I -1.5(11) . . . . ?
C00K C00J C00L C00I -1.5(18) . . . . ?
C00L C00J C00K C00E 1.1(16) . . . . ?

_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 3.038
_oxdiff_exptl_absorpt_empirical_full_min 0.257
