# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_s
_database_code_depnum_ccdc_archive 'CCDC 2314339'
loop_
_audit_author_name
_audit_author_address
'Hai Huang'
;Changzhou University
China
;
_audit_update_record             
;
2023-12-14 deposited with the CCDC.	2026-06-10 downloaded from the CCDC.
;
_audit_creation_date             2023-07-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 I N O3'
_chemical_formula_sum            'C17 H12 I N O3'
_chemical_formula_weight         405.18
_chemical_melting_point          ?
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5414(15)
_cell_length_b                   15.262(2)
_cell_length_c                   8.3665(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.948(4)
_cell_angle_gamma                90
_cell_volume                     1465.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    235.00
_cell_measurement_theta_max      68.509
_cell_measurement_theta_min      2.896
_shelx_estimated_absorpt_T_max   0.277
_shelx_estimated_absorpt_T_min   0.078
_exptl_absorpt_coefficient_mu    17.279
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.2593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1435 before and 0.0901 after correction.
The Ratio of minimum to maximum transmission is 0.3443.
The λ/2 correction factor is Not present.
;
_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    1.836
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17085
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.595
_diffrn_reflns_theta_min         4.820
_diffrn_ambient_temperature      235.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2205
_reflns_number_total             2627
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.355
_refine_diff_density_min         -3.116
_refine_diff_density_rms         0.311
_refine_ls_extinction_coef       0.0036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.272
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2627
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.272
_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)+(0.0806P)²+0.0437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1362
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C16(H16), C9(H9), C5(H5), C3(H3), C13(H13), C7(H7),
 C15(H15), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.39352(3) 0.79526(2) 0.20599(3) 0.0286(2) Uani 1 1 d . . . . .
O1 O 0.5150(3) 0.52674(19) 0.2960(3) 0.0239(7) Uani 1 1 d . . . . .
O3 O 0.6671(3) 0.4717(2) 0.4435(4) 0.0301(8) Uani 1 1 d . . . . .
O2 O 0.6107(3) 0.7654(2) 0.4463(4) 0.0355(9) Uani 1 1 d . . . . .
N1 N 0.6385(4) 0.6192(3) 0.4552(5) 0.0254(9) Uani 1 1 d . . . . .
C1 C 0.3457(4) 0.5613(3) 0.1305(5) 0.0242(10) Uani 1 1 d . . . . .
C4 C 0.6115(4) 0.5354(3) 0.4015(5) 0.0241(10) Uani 1 1 d . . . . .
C6 C 0.8533(4) 0.6392(3) 0.5312(5) 0.0261(10) Uani 1 1 d . . . . .
C8 C 0.4749(4) 0.6781(3) 0.2850(5) 0.0247(10) Uani 1 1 d . . . . .
C10 C 0.8752(6) 0.6958(4) 0.4079(7) 0.0425(15) Uani 1 1 d . . . . .
H10 H 0.813382 0.726989 0.352348 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4440(4) 0.5969(3) 0.2379(5) 0.0218(9) Uani 1 1 d . . . . .
C14 C 0.2391(5) 0.6053(3) 0.1015(6) 0.0309(11) Uani 1 1 d . . . . .
H14 H 0.229333 0.659979 0.149878 0.037 Uiso 1 1 calc R U . . .
C16 C 0.2650(5) 0.4434(3) -0.0411(5) 0.0296(11) Uani 1 1 d . . . . .
H16 H 0.273561 0.388519 -0.089487 0.036 Uiso 1 1 calc R U . . .
C17 C 0.7344(4) 0.6284(3) 0.5858(5) 0.0283(11) Uani 1 1 d . . . . .
H17A H 0.735033 0.576490 0.654790 0.034 Uiso 1 1 calc R U . . .
H17B H 0.718237 0.679289 0.651446 0.034 Uiso 1 1 calc R U . . .
C9 C 0.9889(6) 0.7070(4) 0.3655(8) 0.0483(17) Uani 1 1 d . . . . .
H9 H 1.002398 0.744428 0.280155 0.058 Uiso 1 1 calc R U . . .
C5 C 0.3561(5) 0.4788(3) 0.0586(5) 0.0264(10) Uani 1 1 d . . . . .
H5 H 0.426075 0.447273 0.078580 0.032 Uiso 1 1 calc R U . . .
C11 C 0.5770(5) 0.6934(3) 0.3999(6) 0.0261(11) Uani 1 1 d . . . . .
C3 C 0.1602(5) 0.4892(3) -0.0697(6) 0.0356(12) Uani 1 1 d . . . . .
H3 H 0.098351 0.465468 -0.138125 0.043 Uiso 1 1 calc R U . . .
C13 C 1.0803(5) 0.6634(4) 0.4483(6) 0.0411(13) Uani 1 1 d . . . . .
H13 H 1.156688 0.671790 0.421947 0.049 Uiso 1 1 calc R U . . .
C7 C 0.1478(5) 0.5691(4) 0.0025(7) 0.0385(13) Uani 1 1 d . . . . .
H7 H 0.076772 0.599477 -0.015550 0.046 Uiso 1 1 calc R U . . .
C15 C 0.9470(5) 0.5954(4) 0.6110(6) 0.0376(12) Uani 1 1 d . . . . .
H15 H 0.934184 0.556646 0.694780 0.045 Uiso 1 1 calc R U . . .
C2 C 1.0587(6) 0.6071(4) 0.5706(6) 0.0449(15) Uani 1 1 d . . . . .
H2 H 1.120701 0.576433 0.626865 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C8 2.094(5) . ?
O1 C4 1.353(6) . ?
O1 C12 1.404(5) . ?
O3 C4 1.197(6) . ?
O2 C11 1.215(6) . ?
N1 C4 1.381(6) . ?
N1 C17 1.479(6) . ?
N1 C11 1.390(6) . ?
C1 C12 1.476(7) . ?
C1 C14 1.400(7) . ?
C1 C5 1.406(7) . ?
C6 C10 1.388(7) . ?
C6 C17 1.500(7) . ?
C6 C15 1.383(7) . ?
C8 C12 1.338(6) . ?
C8 C11 1.461(7) . ?
C10 H10 0.9400 . ?
C10 C9 1.404(9) . ?
C14 H14 0.9400 . ?
C14 C7 1.386(7) . ?
C16 H16 0.9400 . ?
C16 C5 1.383(7) . ?
C16 C3 1.395(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C9 H9 0.9400 . ?
C9 C13 1.373(9) . ?
C5 H5 0.9400 . ?
C3 H3 0.9400 . ?
C3 C7 1.375(8) . ?
C13 H13 0.9400 . ?
C13 C2 1.378(8) . ?
C7 H7 0.9400 . ?
C15 H15 0.9400 . ?
C15 C2 1.378(8) . ?
C2 H2 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
C4 O1 C12 124.2(4) . . ?
C4 N1 C17 117.0(4) . . ?
C4 N1 C11 123.8(4) . . ?
C11 N1 C17 119.1(4) . . ?
C14 C1 C12 122.4(4) . . ?
C14 C1 C5 117.9(5) . . ?
C5 C1 C12 119.7(4) . . ?
O1 C4 N1 116.4(4) . . ?
O3 C4 O1 119.4(4) . . ?
O3 C4 N1 124.1(5) . . ?
C10 C6 C17 122.5(5) . . ?
C15 C6 C10 117.8(5) . . ?
C15 C6 C17 119.6(4) . . ?
C12 C8 I1 126.9(4) . . ?
C12 C8 C11 120.9(4) . . ?
C11 C8 I1 112.1(3) . . ?
C6 C10 H10 119.7 . . ?
C6 C10 C9 120.7(6) . . ?
C9 C10 H10 119.7 . . ?
O1 C12 C1 108.4(4) . . ?
C8 C12 O1 118.4(4) . . ?
C8 C12 C1 133.2(5) . . ?
C1 C14 H14 119.6 . . ?
C7 C14 C1 120.9(5) . . ?
C7 C14 H14 119.6 . . ?
C5 C16 H16 120.0 . . ?
C5 C16 C3 119.9(4) . . ?
C3 C16 H16 120.0 . . ?
N1 C17 C6 115.1(3) . . ?
N1 C17 H17A 108.5 . . ?
N1 C17 H17B 108.5 . . ?
C6 C17 H17A 108.5 . . ?
C6 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C10 C9 H9 119.9 . . ?
C13 C9 C10 120.2(5) . . ?
C13 C9 H9 119.9 . . ?
C1 C5 H5 119.5 . . ?
C16 C5 C1 121.0(5) . . ?
C16 C5 H5 119.5 . . ?
O2 C11 N1 119.6(5) . . ?
O2 C11 C8 124.4(5) . . ?
N1 C11 C8 116.0(4) . . ?
C16 C3 H3 120.1 . . ?
C7 C3 C16 119.8(5) . . ?
C7 C3 H3 120.1 . . ?
C9 C13 H13 120.4 . . ?
C9 C13 C2 119.2(5) . . ?
C2 C13 H13 120.4 . . ?
C14 C7 H7 119.7 . . ?
C3 C7 C14 120.5(5) . . ?
C3 C7 H7 119.7 . . ?
C6 C15 H15 119.2 . . ?
C2 C15 C6 121.5(5) . . ?
C2 C15 H15 119.2 . . ?
C13 C2 H2 119.7 . . ?
C15 C2 C13 120.6(5) . . ?
C15 C2 H2 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
I1 C8 C12 O1 175.3(3) . . . . ?
I1 C8 C12 C1 -4.4(7) . . . . ?
I1 C8 C11 O2 0.8(6) . . . . ?
I1 C8 C11 N1 -178.2(3) . . . . ?
C1 C14 C7 C3 -0.1(8) . . . . ?
C4 O1 C12 C1 -178.0(4) . . . . ?
C4 O1 C12 C8 2.2(6) . . . . ?
C4 N1 C17 C6 89.5(5) . . . . ?
C4 N1 C11 O2 -175.6(4) . . . . ?
C4 N1 C11 C8 3.4(7) . . . . ?
C6 C10 C9 C13 -1.5(9) . . . . ?
C6 C15 C2 C13 0.0(8) . . . . ?
C10 C6 C17 N1 45.3(6) . . . . ?
C10 C6 C15 C2 0.1(8) . . . . ?
C10 C9 C13 C2 1.6(9) . . . . ?
C12 O1 C4 O3 -179.5(4) . . . . ?
C12 O1 C4 N1 1.1(6) . . . . ?
C12 C1 C14 C7 -178.7(4) . . . . ?
C12 C1 C5 C16 179.2(4) . . . . ?
C12 C8 C11 O2 179.1(5) . . . . ?
C12 C8 C11 N1 0.1(6) . . . . ?
C14 C1 C12 O1 155.2(4) . . . . ?
C14 C1 C12 C8 -25.2(7) . . . . ?
C14 C1 C5 C16 1.8(6) . . . . ?
C16 C3 C7 C14 1.0(8) . . . . ?
C17 N1 C4 O1 172.3(4) . . . . ?
C17 N1 C4 O3 -7.1(7) . . . . ?
C17 N1 C11 O2 8.2(7) . . . . ?
C17 N1 C11 C8 -172.8(4) . . . . ?
C17 C6 C10 C9 177.0(5) . . . . ?
C17 C6 C15 C2 -176.4(5) . . . . ?
C9 C13 C2 C15 -0.8(9) . . . . ?
C5 C1 C12 O1 -22.2(5) . . . . ?
C5 C1 C12 C8 157.5(5) . . . . ?
C5 C1 C14 C7 -1.3(7) . . . . ?
C5 C16 C3 C7 -0.5(7) . . . . ?
C11 N1 C4 O1 -4.0(6) . . . . ?
C11 N1 C4 O3 176.6(4) . . . . ?
C11 N1 C17 C6 -94.0(5) . . . . ?
C11 C8 C12 O1 -2.7(6) . . . . ?
C11 C8 C12 C1 177.6(4) . . . . ?
C3 C16 C5 C1 -0.9(7) . . . . ?
C15 C6 C10 C9 0.7(8) . . . . ?
C15 C6 C17 N1 -138.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
