# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_NLC_047_A_2_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2533921'
loop_
_audit_author_name
_audit_author_address
'Natalia Calvo'
;Universidad Nacional de Rosario e Instituto de Quimica Rosario
Argentina
;
_audit_update_record             
;
2026-02-27 deposited with the CCDC.	2026-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 I O3'
_chemical_formula_sum            'C17 H13 I O3'
_chemical_formula_weight         392.17

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 0.0000 0.0000 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   17.2784(6)
_cell_length_b                   7.6648(3)
_cell_length_c                   12.0994(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.1900(10)
_cell_angle_gamma                90
_cell_volume                     1546.41(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    16059
_cell_measurement_theta_min      2.4430
_cell_measurement_theta_max      26.2278

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    2.077
_shelx_estimated_absorpt_T_min   0.508
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_process_details   (Krause,SADABS-2016/2)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36185
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_theta_max         26.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3184
_reflns_number_gt                2330
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+6.5623P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3184
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C2 C 0.5442(3) 0.2172(7) 0.4689(4) 0.0411(11) Uani 1 1 d . . . . .
C3 C 0.5225(3) 0.2428(7) 0.5665(4) 0.0435(12) Uani 1 1 d . . . . .
H3 H 0.553795 0.221308 0.640340 0.052 Uiso 1 1 calc R U . . .
O1 O 0.4826(2) 0.2634(5) 0.3740(3) 0.0430(8) Uani 1 1 d . . . . .
C4 C 0.4427(3) 0.3089(6) 0.5356(4) 0.0407(11) Uani 1 1 d . . . . .
C5 C 0.3864(3) 0.3592(6) 0.5940(4) 0.0416(11) Uani 1 1 d . . . . .
H5 H 0.398562 0.354365 0.673481 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3126(3) 0.4158(6) 0.5309(4) 0.0386(11) Uani 1 1 d . . . . .
C7 C 0.2935(3) 0.4300(6) 0.4099(4) 0.0378(10) Uani 1 1 d . . . . .
C8 C 0.3485(3) 0.3797(7) 0.3516(4) 0.0412(11) Uani 1 1 d . . . . .
H8 H 0.337112 0.385366 0.272216 0.049 Uiso 1 1 calc R U . . .
C9 C 0.4213(3) 0.3209(6) 0.4173(4) 0.0386(11) Uani 1 1 d . . . . .
O10 O 0.2194(2) 0.4949(5) 0.3587(3) 0.0438(8) Uani 1 1 d . . . . .
C11 C 0.2013(3) 0.5305(7) 0.2388(4) 0.0450(12) Uani 1 1 d . . . . .
H11A H 0.193285 0.421904 0.196212 0.054 Uiso 1 1 calc R U . . .
H11B H 0.245754 0.592058 0.221464 0.054 Uiso 1 1 calc R U . . .
C12 C 0.1270(3) 0.6396(6) 0.2045(4) 0.0387(11) Uani 1 1 d . . . . .
C13 C 0.0818(3) 0.6390(7) 0.0912(4) 0.0472(12) Uani 1 1 d . . . . .
H13 H 0.096203 0.564978 0.039026 0.057 Uiso 1 1 calc R U . . .
C14 C 0.0161(4) 0.7456(8) 0.0548(5) 0.0562(15) Uani 1 1 d . . . . .
H14 H -0.013149 0.744041 -0.021565 0.067 Uiso 1 1 calc R U . . .
C15 C -0.0061(4) 0.8540(9) 0.1307(5) 0.0618(16) Uani 1 1 d . . . . .
H15 H -0.050916 0.925265 0.106394 0.074 Uiso 1 1 calc R U . . .
C16 C 0.0381(4) 0.8573(9) 0.2436(5) 0.0607(16) Uani 1 1 d . . . . .
H16 H 0.023568 0.932625 0.295039 0.073 Uiso 1 1 calc R U . . .
C17 C 0.1039(3) 0.7490(7) 0.2806(5) 0.0507(13) Uani 1 1 d . . . . .
H17 H 0.132647 0.749968 0.357244 0.061 Uiso 1 1 calc R U . . .
I18 I 0.22527(2) 0.48775(5) 0.61445(3) 0.05692(16) Uani 1 1 d . . . . .
C19 C 0.6162(3) 0.1482(7) 0.4429(5) 0.0469(12) Uani 1 1 d . . . . .
O20 O 0.6216(3) 0.1342(7) 0.3455(4) 0.0706(13) Uani 1 1 d . . . . .
C21 C 0.6839(4) 0.0932(8) 0.5423(5) 0.0592(15) Uani 1 1 d . . . . .
H21A H 0.675319 0.139142 0.611967 0.089 Uiso 1 1 calc R U . . .
H21B H 0.733585 0.137076 0.532094 0.089 Uiso 1 1 calc R U . . .
H21C H 0.686010 -0.031873 0.546442 0.089 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
C2 C3 1.343(7) . ?
C2 O1 1.391(6) . ?
C2 C19 1.461(7) . ?
C3 C4 1.424(7) . ?
C3 H3 0.9300 . ?
O1 C9 1.372(6) . ?
C4 C9 1.385(6) . ?
C4 C5 1.398(7) . ?
C5 C6 1.374(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.418(6) . ?
C6 I18 2.098(5) . ?
C7 O10 1.362(6) . ?
C7 C8 1.379(7) . ?
C8 C9 1.375(7) . ?
C8 H8 0.9300 . ?
O10 C11 1.428(6) . ?
C11 C12 1.498(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.380(7) . ?
C12 C13 1.388(7) . ?
C13 C14 1.373(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(8) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 O20 1.211(6) . ?
C19 C21 1.501(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C3 C2 O1 111.1(4) . . ?
C3 C2 C19 133.7(5) . . ?
O1 C2 C19 115.2(4) . . ?
C2 C3 C4 107.2(4) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
C9 O1 C2 105.5(4) . . ?
C9 C4 C5 118.1(5) . . ?
C9 C4 C3 105.8(4) . . ?
C5 C4 C3 136.1(5) . . ?
C6 C5 C4 118.3(4) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C7 121.9(5) . . ?
C5 C6 I18 119.7(4) . . ?
C7 C6 I18 118.4(4) . . ?
O10 C7 C8 124.2(4) . . ?
O10 C7 C6 115.7(4) . . ?
C8 C7 C6 120.1(4) . . ?
C9 C8 C7 116.4(4) . . ?
C9 C8 H8 121.8 . . ?
C7 C8 H8 121.8 . . ?
O1 C9 C8 124.4(4) . . ?
O1 C9 C4 110.4(4) . . ?
C8 C9 C4 125.1(5) . . ?
C7 O10 C11 117.4(4) . . ?
O10 C11 C12 109.4(4) . . ?
O10 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
O10 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C17 C12 C13 118.4(5) . . ?
C17 C12 C11 122.1(4) . . ?
C13 C12 C11 119.5(5) . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 120.0(5) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 120.3(6) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.3(5) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
O20 C19 C2 121.9(5) . . ?
O20 C19 C21 120.8(5) . . ?
C2 C19 C21 117.3(5) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
O1 C2 C3 C4 0.1(6) . . . . ?
C19 C2 C3 C4 -177.9(6) . . . . ?
C3 C2 O1 C9 0.5(6) . . . . ?
C19 C2 O1 C9 178.9(4) . . . . ?
C2 C3 C4 C9 -0.6(6) . . . . ?
C2 C3 C4 C5 179.1(6) . . . . ?
C9 C4 C5 C6 0.7(7) . . . . ?
C3 C4 C5 C6 -179.0(6) . . . . ?
C4 C5 C6 C7 -2.2(8) . . . . ?
C4 C5 C6 I18 178.8(4) . . . . ?
C5 C6 C7 O10 -177.3(5) . . . . ?
I18 C6 C7 O10 1.7(6) . . . . ?
C5 C6 C7 C8 2.6(8) . . . . ?
I18 C6 C7 C8 -178.3(4) . . . . ?
O10 C7 C8 C9 178.5(5) . . . . ?
C6 C7 C8 C9 -1.4(7) . . . . ?
C2 O1 C9 C8 179.8(5) . . . . ?
C2 O1 C9 C4 -0.9(5) . . . . ?
C7 C8 C9 O1 179.0(5) . . . . ?
C7 C8 C9 C4 -0.1(8) . . . . ?
C5 C4 C9 O1 -178.8(4) . . . . ?
C3 C4 C9 O1 1.0(6) . . . . ?
C5 C4 C9 C8 0.4(8) . . . . ?
C3 C4 C9 C8 -179.8(5) . . . . ?
C8 C7 O10 C11 -7.1(7) . . . . ?
C6 C7 O10 C11 172.8(4) . . . . ?
C7 O10 C11 C12 -166.2(4) . . . . ?
O10 C11 C12 C17 26.7(7) . . . . ?
O10 C11 C12 C13 -156.9(5) . . . . ?
C17 C12 C13 C14 0.7(8) . . . . ?
C11 C12 C13 C14 -175.8(5) . . . . ?
C12 C13 C14 C15 -0.5(9) . . . . ?
C13 C14 C15 C16 0.8(10) . . . . ?
C14 C15 C16 C17 -1.2(10) . . . . ?
C13 C12 C17 C16 -1.2(8) . . . . ?
C11 C12 C17 C16 175.2(5) . . . . ?
C15 C16 C17 C12 1.5(10) . . . . ?
C3 C2 C19 O20 178.6(6) . . . . ?
O1 C2 C19 O20 0.6(8) . . . . ?
C3 C2 C19 C21 -0.9(9) . . . . ?
O1 C2 C19 C21 -178.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 O1 0.93 2.64 3.489(6) 152.3 4_566 yes
C8 H8 O20 0.93 2.59 3.226(6) 126.0 2_655 yes
C11 H11B O20 0.97 2.64 3.560(7) 157.7 2_655 yes

_refine_diff_density_max         0.682
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.103

