# 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_xd-29-1-100k-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2491335'
loop_
_audit_author_name
_audit_author_address
'Dan Xiao'
;Tianjin University
China
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2026-01-05 downloaded from the CCDC.
;
_audit_creation_date             2025-09-25
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H10 I N1.01 O2'
_chemical_formula_sum            'C11 H10 I0 N O'
_chemical_formula_weight         172.20
_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'
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'
I I -0.3257 6.8362 '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                   7.9000(8)
_cell_length_b                   15.6486(13)
_cell_length_c                   15.661(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1936.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    667
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      43.9990
_cell_measurement_theta_min      5.6470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             728
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_Laue_measured_fraction_full 0.883
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1697
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        44.256
_diffrn_reflns_theta_max         44.256
_diffrn_reflns_theta_min         5.650
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     77.00 113.00   0.50    0.05    --   41.77  77.00-180.00   72
  2  ω     18.00  43.00   0.50    0.05    --   41.77  77.00-180.00   50
  3  ω     18.00  45.00   0.50    0.05    --   41.77  77.00 -90.00   54
  4  ω     41.00  66.00   0.50    0.05    --   41.77  57.00   0.00   50
  5  ω     38.00  65.00   0.50    0.05    --   41.77  19.00  60.00   54
  6  ω     49.00 111.00   0.50    0.05    --   41.77  57.00 150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0145962000
_diffrn_orient_matrix_UB_12      0.0710558000
_diffrn_orient_matrix_UB_13      -0.0677458000
_diffrn_orient_matrix_UB_21      -0.0083619000
_diffrn_orient_matrix_UB_22      -0.0677594000
_diffrn_orient_matrix_UB_23      -0.0712087000
_diffrn_orient_matrix_UB_31      -0.1942319000
_diffrn_orient_matrix_UB_32      0.0083299000
_diffrn_orient_matrix_UB_33      -0.0019563000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                488
_reflns_number_total             666
_reflns_odcompleteness_completeness 85.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     44.45
_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 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         666
_refine_ls_number_restraints     194
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      0.898
_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)+10.7929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0789
_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. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00A(H00D), C00C(H00H)
5.b Idealised Me refined as rotating group:
 C008(H00A,H00B,H00C), C00B(H00E,H00F,H00G)
;
_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 0.40773(12) 0.31013(5) 0.43080(6) 0.0377(4) Uani 1 1 d . U . . .
O002 O 0.6396(10) 0.3168(6) 0.5262(6) 0.037(2) Uani 1 1 d . U . . .
O003 O 0.8526(12) 0.4018(5) 0.5653(7) 0.045(3) Uani 1 1 d . U . . .
C004 C 0.6792(18) 0.4415(8) 0.4471(10) 0.029(3) Uani 1 1 d . U . . .
N005 N 0.2386(15) 0.3302(7) 0.3328(8) 0.045(4) Uani 1.01(3) 1 d . U . . .
C006 C 0.731(2) 0.3849(10) 0.5193(11) 0.040(4) Uani 1 1 d . U . . .
C007 C 0.7731(18) 0.5150(8) 0.4254(10) 0.033(3) Uani 1 1 d . U . . .
H007 H 0.869180 0.530225 0.458534 0.040 Uiso 1 1 calc R . . . .
C008 C 0.071(2) 0.3611(9) 0.3652(10) 0.054(5) Uani 1 1 d . U . . .
H00A H 0.019472 0.316718 0.400723 0.081 Uiso 1 1 calc GR . . . .
H00B H -0.002879 0.374002 0.316825 0.081 Uiso 1 1 calc GR . . . .
H00C H 0.088269 0.412897 0.399395 0.081 Uiso 1 1 calc GR . . . .
C009 C 0.584(2) 0.5461(8) 0.3108(10) 0.041(4) Uani 1 1 d . U . . .
H009 H 0.549197 0.582245 0.265352 0.050 Uiso 1 1 calc R . . . .
C00A C 0.4880(19) 0.4731(9) 0.3310(10) 0.039(4) Uani 1 1 d . U . . .
H00D H 0.389031 0.459517 0.299244 0.047 Uiso 1 1 calc R . . . .
C00B C 0.2185(19) 0.2542(9) 0.2786(9) 0.046(4) Uani 1 1 d . U . . .
H00E H 0.330257 0.231555 0.263635 0.068 Uiso 1 1 calc GR . . . .
H00F H 0.157628 0.269896 0.226336 0.068 Uiso 1 1 calc GR . . . .
H00G H 0.154131 0.210596 0.309572 0.068 Uiso 1 1 calc GR . . . .
C00C C 0.727(2) 0.5656(9) 0.3557(10) 0.043(4) Uani 1 1 d . U . . .
H00H H 0.794151 0.613271 0.339751 0.051 Uiso 1 1 calc R . . . .
C00D C 0.5397(19) 0.4217(9) 0.3974(11) 0.040(4) Uani 1 1 d . 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 O002 2.366(9) . ?
I001 N005 2.059(12) . ?
I001 C00D 2.100(14) . ?
O002 C006 1.294(16) . ?
O003 C006 1.227(16) . ?
C004 C006 1.50(2) . ?
C004 C007 1.410(18) . ?
C004 C00D 1.385(18) . ?
N005 C008 1.495(18) . ?
N005 C00B 1.470(15) . ?
C007 H007 0.9500 . ?
C007 C00C 1.397(17) . ?
C008 H00A 0.9800 . ?
C008 H00B 0.9800 . ?
C008 H00C 0.9800 . ?
C009 H009 0.9500 . ?
C009 C00A 1.408(18) . ?
C009 C00C 1.362(19) . ?
C00A H00D 0.9500 . ?
C00A C00D 1.376(18) . ?
C00B H00E 0.9800 . ?
C00B H00F 0.9800 . ?
C00B H00G 0.9800 . ?
C00C H00H 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
N005 I001 O002 165.1(4) . . ?
N005 I001 C00D 90.5(6) . . ?
C00D I001 O002 74.7(5) . . ?
C006 O002 I001 114.7(10) . . ?
C007 C004 C006 121.3(15) . . ?
C00D C004 C006 120.8(14) . . ?
C00D C004 C007 117.8(15) . . ?
C008 N005 I001 111.7(9) . . ?
C00B N005 I001 112.2(8) . . ?
C00B N005 C008 111.2(12) . . ?
O002 C006 C004 113.3(15) . . ?
O003 C006 O002 124.5(15) . . ?
O003 C006 C004 122.1(15) . . ?
C004 C007 H007 119.6 . . ?
C00C C007 C004 120.8(15) . . ?
C00C C007 H007 119.6 . . ?
N005 C008 H00A 109.5 . . ?
N005 C008 H00B 109.5 . . ?
N005 C008 H00C 109.5 . . ?
H00A C008 H00B 109.5 . . ?
H00A C008 H00C 109.5 . . ?
H00B C008 H00C 109.5 . . ?
C00A C009 H009 119.6 . . ?
C00C C009 H009 119.6 . . ?
C00C C009 C00A 120.8(15) . . ?
C009 C00A H00D 120.6 . . ?
C00D C00A C009 118.9(15) . . ?
C00D C00A H00D 120.6 . . ?
N005 C00B H00E 109.5 . . ?
N005 C00B H00F 109.5 . . ?
N005 C00B H00G 109.5 . . ?
H00E C00B H00F 109.5 . . ?
H00E C00B H00G 109.5 . . ?
H00F C00B H00G 109.5 . . ?
C007 C00C H00H 120.2 . . ?
C009 C00C C007 119.5(15) . . ?
C009 C00C H00H 120.2 . . ?
C004 C00D I001 116.2(12) . . ?
C00A C00D I001 121.8(12) . . ?
C00A C00D C004 122.0(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.751
