# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2336194'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;

_audit_creation_date             2024-02-29T16:03:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C13 H16 I N O2'
_chemical_formula_sum            'C13 H16 I N O2'
_chemical_formula_weight         345.17
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4287(7)
_cell_length_b                   8.9764(12)
_cell_length_c                   13.4695(16)
_cell_angle_alpha                96.706(11)
_cell_angle_beta                 95.087(10)
_cell_angle_gamma                90.122(11)
_cell_volume                     649.26(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    1486
_cell_measurement_theta_min      4.0330
_cell_measurement_theta_max      25.3720
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.456
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, EosS2, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_number            4332
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.597
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             2289
_reflns_number_gt                1994
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2289
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1372
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.734
_refine_diff_density_min         -1.362
_refine_diff_density_rms         0.186

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.9868(13) 0.2935(9) 0.2251(5) 0.0210(17) Uani 1 1 d . . . . .
C2 C 1.0653(14) 0.1537(9) 0.1553(5) 0.0233(18) Uani 1 1 d . . . . .
H2 H 1.163377 0.067338 0.177237 0.028 Uiso 1 1 calc R U . . .
C3 C 0.8018(14) 0.1437(9) 0.0985(5) 0.0230(17) Uani 1 1 d . . . . .
H3 H 0.702973 0.04923 0.077903 0.028 Uiso 1 1 calc R U . . .
C4 C 0.7199(14) 0.2813(10) 0.1692(6) 0.0270(19) Uani 1 1 d . . . . .
H4 H 0.56265 0.287153 0.202879 0.032 Uiso 1 1 calc R U . . .
C5 C 1.0685(14) 0.4017(10) 0.1531(5) 0.0255(18) Uani 1 1 d . . . . .
H5 H 1.168612 0.495696 0.173369 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7996(15) 0.3923(9) 0.0959(5) 0.0263(18) Uani 1 1 d . . . . .
H6 H 0.701446 0.478495 0.073677 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8888(13) 0.2524(9) 0.0255(5) 0.0197(16) Uani 1 1 d . . . . .
C8 C 1.1463(15) 0.2648(10) 0.0824(5) 0.0260(18) Uani 1 1 d . . . . .
H8 H 1.30496 0.258216 0.04973 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6604(14) 0.2228(9) -0.1400(5) 0.0247(18) Uani 1 1 d . . . . .
C10 C 0.5035(13) 0.1932(10) -0.3193(5) 0.0219(17) Uani 1 1 d . . . . .
C11 C 0.3516(16) 0.0537(11) -0.3159(6) 0.035(2) Uani 1 1 d . . . . .
H11A H 0.21837 0.045768 -0.370353 0.053 Uiso 1 1 calc R U . . .
H11B H 0.457375 -0.034491 -0.32379 0.053 Uiso 1 1 calc R U . . .
H11C H 0.280247 0.058891 -0.251236 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6484(16) 0.1798(12) -0.4116(6) 0.037(2) Uani 1 1 d . . . . .
H12A H 0.533042 0.170479 -0.472233 0.056 Uiso 1 1 calc R U . . .
H12B H 0.752725 0.269489 -0.40988 0.056 Uiso 1 1 calc R U . . .
H12C H 0.75286 0.090869 -0.411962 0.056 Uiso 1 1 calc R U . . .
C13 C 0.3504(16) 0.3348(11) -0.3139(6) 0.035(2) Uani 1 1 d . . . . .
H13A H 0.217622 0.324983 -0.368639 0.053 Uiso 1 1 calc R U . . .
H13B H 0.278411 0.349862 -0.24938 0.053 Uiso 1 1 calc R U . . .
H13C H 0.456365 0.421079 -0.320399 0.053 Uiso 1 1 calc R U . . .
I1 I 1.06834(10) 0.32502(7) 0.38262(4) 0.0339(2) Uani 1 1 d . . . . .
N1 N 0.8712(11) 0.2325(8) -0.0811(4) 0.0233(15) Uani 1 1 d . . . . .
H1 H 1.010114 0.226211 -0.110279 0.028 Uiso 1 1 calc R U . . .
O1 O 0.4530(9) 0.2286(7) -0.1085(4) 0.0280(13) Uani 1 1 d . . . . .
O2 O 0.7061(9) 0.2060(7) -0.2368(3) 0.0241(13) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C5 1.541(11) . ?
C1 C2 1.562(11) . ?
C1 C4 1.570(10) . ?
C1 I1 2.115(7) . ?
C2 C3 1.558(11) . ?
C2 C8 1.566(11) . ?
C3 C4 1.560(12) . ?
C3 C7 1.565(10) . ?
C4 C6 1.568(11) . ?
C5 C8 1.548(12) . ?
C5 C6 1.587(11) . ?
C6 C7 1.587(11) . ?
C7 N1 1.420(9) . ?
C7 C8 1.531(10) . ?
C9 O1 1.237(9) . ?
C9 N1 1.330(10) . ?
C9 O2 1.340(8) . ?
C10 O2 1.487(9) . ?
C10 C11 1.506(12) . ?
C10 C13 1.518(12) . ?
C10 C12 1.523(10) . ?

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
C5 C1 C2 91.9(6) . . ?
C5 C1 C4 90.9(5) . . ?
C2 C1 C4 89.8(6) . . ?
C5 C1 I1 124.4(5) . . ?
C2 C1 I1 124.3(5) . . ?
C4 C1 I1 125.2(5) . . ?
C3 C2 C1 90.2(6) . . ?
C3 C2 C8 89.6(5) . . ?
C1 C2 C8 87.6(6) . . ?
C2 C3 C4 90.2(6) . . ?
C2 C3 C7 89.4(6) . . ?
C4 C3 C7 89.7(6) . . ?
C3 C4 C6 91.3(5) . . ?
C3 C4 C1 89.8(6) . . ?
C6 C4 C1 89.7(6) . . ?
C1 C5 C8 89.1(6) . . ?
C1 C5 C6 90.1(6) . . ?
C8 C5 C6 90.0(6) . . ?
C4 C6 C5 89.3(5) . . ?
C4 C6 C7 88.6(6) . . ?
C5 C6 C7 88.0(6) . . ?
N1 C7 C8 118.4(6) . . ?
N1 C7 C3 128.7(7) . . ?
C8 C7 C3 90.6(5) . . ?
N1 C7 C6 127.2(6) . . ?
C8 C7 C6 90.5(6) . . ?
C3 C7 C6 90.4(5) . . ?
C7 C8 C5 91.5(6) . . ?
C7 C8 C2 90.3(6) . . ?
C5 C8 C2 91.4(6) . . ?
O1 C9 N1 124.0(6) . . ?
O1 C9 O2 125.6(7) . . ?
N1 C9 O2 110.4(6) . . ?
O2 C10 C11 109.8(6) . . ?
O2 C10 C13 110.3(6) . . ?
C11 C10 C13 113.0(7) . . ?
O2 C10 C12 101.5(6) . . ?
C11 C10 C12 111.2(7) . . ?
C13 C10 C12 110.5(7) . . ?
C9 N1 C7 124.9(6) . . ?
C9 O2 C10 121.9(6) . . ?

