# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_paei_auto
_database_code_depnum_ccdc_archive 'CCDC 2220478'
loop_
_audit_author_name
_audit_author_address
'WANG YAO'
;FUZ University
China
;
_audit_update_record             
;
2024-01-20 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 I1 N2 O2'
_chemical_formula_sum            'C10 H11 I0.75 N2 O2'
_chemical_formula_weight         286.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0030 5.4350 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8409(3)
_cell_length_b                   11.5206(4)
_cell_length_c                   12.2248(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.795(4)
_cell_angle_gamma                90
_cell_volume                     1103.75(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6698
_cell_measurement_theta_min      4.5640
_cell_measurement_theta_max      60.3220

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             563
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.012
_exptl_crystal_size_mid          0.011
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    11.778
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.3405
_diffrn_radiation_type           GaK\a
_diffrn_source                   'micro-focus metaljet'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            12311
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.586
_diffrn_reflns_theta_max         60.110
_diffrn_reflns_theta_full        53.543
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2449
_reflns_number_gt                2208
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0775P)²+2.0623P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2449
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.002
_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
O1 O 0.5085(5) 0.6410(3) 0.4116(3) 0.0386(8) Uani 1 1 d . . . . .
O2 O 0.6848(5) 0.9068(3) 0.6675(3) 0.0420(9) Uani 1 1 d . . . . .
N1 N 0.5771(5) 0.7577(3) 0.5598(3) 0.0325(9) Uani 1 1 d . . . . .
N2 N 0.7442(5) 0.5328(3) 0.6372(3) 0.0334(9) Uani 1 1 d . . . . .
H2A H 0.809946 0.571871 0.589406 0.040 Uiso 1 1 calc R U . . .
H2B H 0.664470 0.490252 0.599231 0.040 Uiso 1 1 calc R U . . .
H2C H 0.811108 0.484751 0.679069 0.040 Uiso 1 1 calc R U . . .
C6 C 0.6151(6) 0.8369(4) 0.3906(4) 0.0318(10) Uani 1 1 d . . . . .
C1 C 0.6188(7) 0.8620(4) 0.2798(4) 0.0366(11) Uani 1 1 d . . . . .
H1 H 0.577125 0.808270 0.226423 0.044 Uiso 1 1 calc R U . . .
C5 C 0.6761(6) 0.9169(4) 0.4686(4) 0.0336(10) Uani 1 1 d . . . . .
C10 C 0.6567(7) 0.6180(4) 0.7093(4) 0.0344(11) Uani 1 1 d . . . . .
H10A H 0.741844 0.673784 0.739570 0.041 Uiso 1 1 calc R U . . .
H10B H 0.607189 0.575945 0.771456 0.041 Uiso 1 1 calc R U . . .
C7 C 0.5583(6) 0.7330(4) 0.4486(4) 0.0314(10) Uani 1 1 d . . . . .
C2 C 0.6857(7) 0.9686(5) 0.2495(4) 0.0395(12) Uani 1 1 d . . . . .
H2 H 0.685534 0.988940 0.174234 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5159(7) 0.6842(4) 0.6476(5) 0.0351(11) Uani 1 1 d . . . . .
H9A H 0.432765 0.627791 0.616126 0.042 Uiso 1 1 calc R U . . .
H9B H 0.455044 0.733368 0.700196 0.042 Uiso 1 1 calc R U . . .
C8 C 0.6511(6) 0.8657(4) 0.5779(4) 0.0337(11) Uani 1 1 d . . . . .
C4 C 0.7483(7) 1.0214(4) 0.4389(5) 0.0389(11) Uani 1 1 d . . . . .
H4 H 0.792754 1.074046 0.492383 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7534(8) 1.0467(4) 0.3271(5) 0.0446(13) Uani 1 1 d . . . . .
H3 H 0.803071 1.117312 0.303682 0.054 Uiso 1 1 calc R U . . .
I1 I 1.02706(4) 0.69497(2) 0.47126(2) 0.01626(18) Uani 0.75 1 d . . P A 1


_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
O1 C7 1.213(6) . ?
O2 C8 1.215(6) . ?
N1 C8 1.388(6) . ?
N1 C7 1.391(6) . ?
N1 C9 1.461(7) . ?
N2 C10 1.499(6) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
C6 C1 1.387(7) . ?
C6 C5 1.399(7) . ?
C6 C7 1.468(7) . ?
C1 C2 1.390(8) . ?
C1 H1 0.9500 . ?
C5 C4 1.384(7) . ?
C5 C8 1.479(7) . ?
C10 C9 1.523(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C2 C3 1.399(8) . ?
C2 H2 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 C3 1.399(8) . ?
C4 H4 0.9500 . ?
C3 H3 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
C8 N1 C7 111.7(4) . . ?
C8 N1 C9 123.2(4) . . ?
C7 N1 C9 124.9(4) . . ?
C10 N2 H2A 109.5 . . ?
C10 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C10 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C1 C6 C5 120.8(5) . . ?
C1 C6 C7 131.2(5) . . ?
C5 C6 C7 108.1(4) . . ?
C6 C1 C2 117.6(5) . . ?
C6 C1 H1 121.2 . . ?
C2 C1 H1 121.2 . . ?
C4 C5 C6 121.8(5) . . ?
C4 C5 C8 130.6(5) . . ?
C6 C5 C8 107.5(4) . . ?
N2 C10 C9 112.0(4) . . ?
N2 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O1 C7 N1 124.5(5) . . ?
O1 C7 C6 129.2(5) . . ?
N1 C7 C6 106.3(4) . . ?
C1 C2 C3 121.7(5) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
N1 C9 C10 113.9(5) . . ?
N1 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O2 C8 N1 124.8(5) . . ?
O2 C8 C5 128.9(5) . . ?
N1 C8 C5 106.3(4) . . ?
C5 C4 C3 117.5(5) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 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
C5 C6 C1 C2 0.3(7) . . . . ?
C7 C6 C1 C2 -178.1(5) . . . . ?
C1 C6 C5 C4 -2.6(8) . . . . ?
C7 C6 C5 C4 176.1(5) . . . . ?
C1 C6 C5 C8 178.8(4) . . . . ?
C7 C6 C5 C8 -2.4(5) . . . . ?
C8 N1 C7 O1 174.4(5) . . . . ?
C9 N1 C7 O1 -9.9(8) . . . . ?
C8 N1 C7 C6 -3.8(5) . . . . ?
C9 N1 C7 C6 171.9(4) . . . . ?
C1 C6 C7 O1 4.3(9) . . . . ?
C5 C6 C7 O1 -174.3(5) . . . . ?
C1 C6 C7 N1 -177.6(5) . . . . ?
C5 C6 C7 N1 3.8(5) . . . . ?
C6 C1 C2 C3 2.4(8) . . . . ?
C8 N1 C9 C10 -79.1(6) . . . . ?
C7 N1 C9 C10 105.7(5) . . . . ?
N2 C10 C9 N1 -64.0(5) . . . . ?
C7 N1 C8 O2 -178.4(5) . . . . ?
C9 N1 C8 O2 5.8(8) . . . . ?
C7 N1 C8 C5 2.3(6) . . . . ?
C9 N1 C8 C5 -173.5(4) . . . . ?
C4 C5 C8 O2 2.6(9) . . . . ?
C6 C5 C8 O2 -179.1(5) . . . . ?
C4 C5 C8 N1 -178.2(5) . . . . ?
C6 C5 C8 N1 0.2(5) . . . . ?
C6 C5 C4 C3 2.1(8) . . . . ?
C8 C5 C4 C3 -179.7(5) . . . . ?
C5 C4 C3 C2 0.6(8) . . . . ?
C1 C2 C3 C4 -2.9(9) . . . . ?

_refine_diff_density_max         1.316
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.165



