# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_1120-a_auto
_database_code_depnum_ccdc_archive 'CCDC 2443197'
loop_
_audit_author_name
_audit_author_address
'Yan Tang'
;yunnan mingzu university
China
;
_audit_update_record             
;
2025-04-11 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
_audit_creation_date             2024-11-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C12 H10 I N O'
_chemical_formula_sum            'C12 H10 I N O'
_chemical_formula_weight         311.11
_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 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   12.7130(3)
_cell_length_b                   9.9112(3)
_cell_length_c                   17.8424(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2248.16(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5189
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.2740
_cell_measurement_theta_min      3.9680
_shelx_estimated_absorpt_T_max   0.896
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    2.821
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.838
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.339
_diffrn_reflns_theta_min         3.465
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  42.00   1.00    8.55    --   16.70  77.00   0.00   52
  2  ω    -10.00  42.00   1.00    8.55    --   16.70  77.00 120.00   52
  3  ω      0.00  84.00   1.00    8.55    --   16.70  57.00 -90.00   84
  4  ω      0.00  84.00   1.00    8.55    --   16.70  57.00  30.00   84
  5  ω    -10.00  42.00   1.00    8.55    --   16.70  77.00  90.00   52
  6  ω    -15.00  21.00   1.00    8.55    --   16.70 -99.00 -30.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0474001000
_diffrn_orient_matrix_UB_12      -0.0242004000
_diffrn_orient_matrix_UB_13      -0.0161136000
_diffrn_orient_matrix_UB_21      -0.0124072000
_diffrn_orient_matrix_UB_22      0.0335200000
_diffrn_orient_matrix_UB_23      -0.0339938000
_diffrn_orient_matrix_UB_31      0.0267064000
_diffrn_orient_matrix_UB_32      0.0584296000
_diffrn_orient_matrix_UB_33      0.0128072000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1939
_reflns_number_total             2840
_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 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.037
_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)+(0.0251P)²+3.2750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0823
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 H11B-C11
 0.95 with sigma of 0.002
 C11-H11A
 0.95 with sigma of 0.002
3.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8), C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C1(H1), C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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 0.25027(2) 0.52441(3) 0.54488(2) 0.05942(12) Uani 1 1 d . . . . .
O1 O 0.3187(2) 0.4497(2) 0.35776(14) 0.0495(6) Uani 1 1 d . . . . .
C9 C 0.2891(2) 0.6247(3) 0.44052(17) 0.0345(7) Uani 1 1 d . . . . .
H9 H 0.311998 0.717298 0.450650 0.041 Uiso 1 1 calc R U . . .
C5 C 0.3427(3) 0.6371(3) 0.28472(18) 0.0418(8) Uani 1 1 d . . . . .
C4 C 0.4198(3) 0.6382(3) 0.33972(19) 0.0413(7) Uani 1 1 d . . . . .
C10 C 0.2014(2) 0.6251(3) 0.37918(17) 0.0328(6) Uani 1 1 d . . . . .
C11 C 0.0920(3) 0.5634(3) 0.3997(2) 0.0408(8) Uani 1 1 d D . . . .
N1 N -0.0082(3) 0.7281(4) 0.4846(2) 0.0712(11) Uani 1 1 d . . . . .
C8 C 0.2578(3) 0.5465(3) 0.3158(2) 0.0430(8) Uani 1 1 d . . . . .
H8 H 0.210860 0.507237 0.278099 0.052 Uiso 1 1 calc R U . . .
C12 C 0.0367(3) 0.6507(4) 0.4475(2) 0.0509(9) Uani 1 1 d . . . . .
C7 C 0.3776(3) 0.5466(3) 0.4010(2) 0.0434(8) Uani 1 1 d . . . . .
H7 H 0.430968 0.508076 0.434330 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3517(3) 0.7172(4) 0.2218(2) 0.0532(9) Uani 1 1 d . . . . .
H6 H 0.299360 0.718656 0.185387 0.064 Uiso 1 1 calc R U . . .
C3 C 0.5087(3) 0.7170(4) 0.3328(2) 0.0542(10) Uani 1 1 d . . . . .
H3 H 0.560062 0.717992 0.369898 0.065 Uiso 1 1 calc R U . . .
C1 C 0.4414(4) 0.7954(4) 0.2146(2) 0.0625(12) Uani 1 1 d . . . . .
H1 H 0.449686 0.849458 0.172461 0.075 Uiso 1 1 calc R U . . .
C2 C 0.5186(3) 0.7946(4) 0.2686(2) 0.0635(12) Uani 1 1 d . . . . .
H2 H 0.578456 0.847142 0.261974 0.076 Uiso 1 1 calc R U . . .
H10 H 0.191(2) 0.708(3) 0.3665(16) 0.025(8) Uiso 1 1 d . . . . .
H11A H 0.093(2) 0.4737(11) 0.4183(16) 0.034(8) Uiso 1 1 d D . . . .
H11B H 0.057(2) 0.555(3) 0.3528(8) 0.036(8) Uiso 1 1 d D . . . .


_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 C9 2.168(3) . ?
O1 C8 1.442(4) . ?
O1 C7 1.442(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.563(4) . ?
C9 C7 1.536(4) . ?
C5 C4 1.388(5) . ?
C5 C8 1.509(5) . ?
C5 C6 1.380(5) . ?
C4 C7 1.519(5) . ?
C4 C3 1.378(5) . ?
C10 C11 1.563(4) . ?
C10 C8 1.549(4) . ?
C10 H10 0.86(3) . ?
C11 C12 1.404(5) . ?
C11 H11A 0.949(2) . ?
C11 H11B 0.949(2) . ?
N1 C12 1.164(5) . ?
C8 H8 0.9800 . ?
C7 H7 0.9800 . ?
C6 H6 0.9300 . ?
C6 C1 1.384(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.385(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.375(6) . ?
C2 H2 0.9300 . ?

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
C7 O1 C8 96.5(2) . . ?
I1 C9 H9 109.8 . . ?
C10 C9 I1 116.1(2) . . ?
C10 C9 H9 109.8 . . ?
C7 C9 I1 109.3(2) . . ?
C7 C9 H9 109.8 . . ?
C7 C9 C10 101.7(2) . . ?
C4 C5 C8 104.5(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 C8 134.5(3) . . ?
C5 C4 C7 104.7(3) . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 C7 133.8(3) . . ?
C9 C10 H10 107(2) . . ?
C11 C10 C9 118.1(3) . . ?
C11 C10 H10 107(2) . . ?
C8 C10 C9 100.3(3) . . ?
C8 C10 C11 112.7(3) . . ?
C8 C10 H10 111(2) . . ?
C10 C11 H11A 116(2) . . ?
C10 C11 H11B 104.0(19) . . ?
C12 C11 C10 110.2(3) . . ?
C12 C11 H11A 111.7(19) . . ?
C12 C11 H11B 111.1(19) . . ?
H11A C11 H11B 103(3) . . ?
O1 C8 C5 101.7(3) . . ?
O1 C8 C10 101.8(3) . . ?
O1 C8 H8 114.8 . . ?
C5 C8 C10 107.5(3) . . ?
C5 C8 H8 114.8 . . ?
C10 C8 H8 114.8 . . ?
N1 C12 C11 176.7(4) . . ?
O1 C7 C9 101.6(3) . . ?
O1 C7 C4 101.3(3) . . ?
O1 C7 H7 115.1 . . ?
C9 C7 H7 115.1 . . ?
C4 C7 C9 106.8(3) . . ?
C4 C7 H7 115.1 . . ?
C5 C6 H6 121.1 . . ?
C5 C6 C1 117.7(4) . . ?
C1 C6 H6 121.1 . . ?
C4 C3 H3 121.2 . . ?
C4 C3 C2 117.6(4) . . ?
C2 C3 H3 121.2 . . ?
C6 C1 H1 119.3 . . ?
C2 C1 C6 121.3(4) . . ?
C2 C1 H1 119.3 . . ?
C3 C2 H2 119.4 . . ?
C1 C2 C3 121.2(4) . . ?
C1 C2 H2 119.4 . . ?

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 C9 C10 C11 4.2(4) . . . . ?
I1 C9 C10 C8 -118.6(2) . . . . ?
I1 C9 C7 O1 88.1(2) . . . . ?
I1 C9 C7 C4 -166.1(2) . . . . ?
C9 C10 C11 C12 73.9(4) . . . . ?
C9 C10 C8 O1 35.4(3) . . . . ?
C9 C10 C8 C5 -71.0(3) . . . . ?
C5 C4 C7 O1 32.4(3) . . . . ?
C5 C4 C7 C9 -73.5(3) . . . . ?
C5 C4 C3 C2 -0.4(5) . . . . ?
C5 C6 C1 C2 -0.7(6) . . . . ?
C4 C5 C8 O1 -33.4(3) . . . . ?
C4 C5 C8 C10 73.1(3) . . . . ?
C4 C5 C6 C1 1.7(5) . . . . ?
C4 C3 C2 C1 1.5(6) . . . . ?
C10 C9 C7 O1 -35.2(3) . . . . ?
C10 C9 C7 C4 70.6(3) . . . . ?
C11 C10 C8 O1 -91.1(3) . . . . ?
C11 C10 C8 C5 162.5(3) . . . . ?
C8 O1 C7 C9 58.2(3) . . . . ?
C8 O1 C7 C4 -51.7(3) . . . . ?
C8 C5 C4 C7 0.6(3) . . . . ?
C8 C5 C4 C3 -176.6(3) . . . . ?
C8 C5 C6 C1 175.4(3) . . . . ?
C8 C10 C11 C12 -169.8(3) . . . . ?
C7 O1 C8 C5 52.4(3) . . . . ?
C7 O1 C8 C10 -58.5(3) . . . . ?
C7 C9 C10 C11 122.7(3) . . . . ?
C7 C9 C10 C8 -0.1(3) . . . . ?
C7 C4 C3 C2 -176.5(4) . . . . ?
C6 C5 C4 C7 175.9(3) . . . . ?
C6 C5 C4 C3 -1.2(5) . . . . ?
C6 C5 C8 O1 152.3(4) . . . . ?
C6 C5 C8 C10 -101.2(4) . . . . ?
C6 C1 C2 C3 -0.9(6) . . . . ?
C3 C4 C7 O1 -151.1(4) . . . . ?
C3 C4 C7 C9 103.0(4) . . . . ?

_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.861
####################################################################### 
# 
# 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_1120-b_auto
_database_code_depnum_ccdc_archive 'CCDC 2443198'
loop_
_audit_author_name
_audit_author_address
'Yan Tang'
;yunnan mingzu university
China
;
_audit_update_record             
;
2025-04-11 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
_audit_creation_date             2024-11-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C12 H10 I N O'
_chemical_formula_sum            'C12 H10 I N O'
_chemical_formula_weight         311.11
_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 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   13.9738(8)
_cell_length_b                   8.8365(4)
_cell_length_c                   9.5185(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.071(6)
_cell_angle_gamma                90
_cell_volume                     1153.47(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4509
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.3760
_cell_measurement_theta_min      4.3370
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.831
_exptl_absorpt_coefficient_mu    2.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.792
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9557
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.304
_diffrn_reflns_theta_min         3.322
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -39.00   1.00    2.57    --  -15.92-178.00   0.00   49
  2  ω    -45.00  55.00   1.00    2.57    --  -15.92  19.00  60.00  100
  3  ω    -45.00  55.00   1.00    2.57    --  -15.92  19.00 -30.00  100
  4  ω    -50.00  30.00   1.00    2.57    --   16.85 -57.00-180.00   80
  5  ω    -10.00  42.00   1.00    2.57    --   16.85  77.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0477129000
_diffrn_orient_matrix_UB_12      0.0165421000
_diffrn_orient_matrix_UB_13      0.0377457000
_diffrn_orient_matrix_UB_21      -0.0192513000
_diffrn_orient_matrix_UB_22      0.0545328000
_diffrn_orient_matrix_UB_23      0.0416307000
_diffrn_orient_matrix_UB_31      -0.0048435000
_diffrn_orient_matrix_UB_32      -0.0566312000
_diffrn_orient_matrix_UB_33      0.0510556000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2282
_reflns_number_total             2795
_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 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.376
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.071
_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)+(0.0351P)²+0.2292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0844
_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 Ternary CH refined with riding coordinates:
 C003(H003), C004(H004), C009(H009), C00B(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00D), C00D(H00E), C00E(H00F), C00F(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 0.67220(2) 0.33226(3) 0.26562(2) 0.05262(12) Uani 1 1 d . . . . .
O002 O 0.87964(16) 0.6053(3) 0.5426(2) 0.0428(5) Uani 1 1 d . . . . .
C003 C 0.8022(2) 0.4429(3) 0.3725(3) 0.0351(6) Uani 1 1 d . . . . .
H003 H 0.855744 0.369607 0.385152 0.042 Uiso 1 1 calc R U . . .
C004 C 0.8330(2) 0.5843(3) 0.2952(3) 0.0316(6) Uani 1 1 d . . . . .
H004 H 0.780607 0.615422 0.216639 0.038 Uiso 1 1 calc R U . . .
C005 C 0.7469(2) 0.7457(4) 0.4410(3) 0.0338(6) Uani 1 1 d . . . . .
C006 C 0.7125(2) 0.6204(4) 0.5054(3) 0.0366(7) Uani 1 1 d . . . . .
C007 C 0.9287(2) 0.5609(4) 0.2409(3) 0.0401(7) Uani 1 1 d . . . . .
H00A H 0.947424 0.655759 0.202565 0.048 Uiso 1 1 calc R U . . .
H00B H 0.979646 0.532846 0.320916 0.048 Uiso 1 1 calc R U . . .
N008 N 0.9145(3) 0.3555(4) 0.0436(5) 0.0761(12) Uani 1 1 d . . . . .
C009 C 0.7946(2) 0.5068(4) 0.5204(3) 0.0397(7) Uani 1 1 d . . . . .
H009 H 0.794595 0.430442 0.595044 0.048 Uiso 1 1 calc R U . . .
C00A C 0.9211(2) 0.4451(4) 0.1311(4) 0.0456(8) Uani 1 1 d . . . . .
C00B C 0.8461(2) 0.7017(3) 0.4186(3) 0.0363(7) Uani 1 1 d . . . . .
H00C H 0.889293 0.786711 0.408247 0.044 Uiso 1 1 calc R U . . .
C00C C 0.6894(3) 0.8731(4) 0.4059(3) 0.0438(8) Uani 1 1 d . . . . .
H00D H 0.711892 0.955970 0.361458 0.053 Uiso 1 1 calc R U . . .
C00D C 0.6207(3) 0.6194(5) 0.5370(4) 0.0514(9) Uani 1 1 d . . . . .
H00E H 0.597668 0.535688 0.579497 0.062 Uiso 1 1 calc R U . . .
C00E C 0.5976(3) 0.8724(5) 0.4391(4) 0.0573(10) Uani 1 1 d . . . . .
H00F H 0.558104 0.957263 0.418055 0.069 Uiso 1 1 calc R U . . .
C00F C 0.5628(3) 0.7492(5) 0.5029(4) 0.0575(10) Uani 1 1 d . . . . .
H00G H 0.500358 0.752083 0.523423 0.069 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
I001 C003 2.140(3) . ?
O002 C009 1.455(4) . ?
O002 C00B 1.458(3) . ?
C003 H003 0.9800 . ?
C003 C004 1.553(4) . ?
C003 C009 1.539(4) . ?
C004 H004 0.9800 . ?
C004 C007 1.536(4) . ?
C004 C00B 1.552(4) . ?
C005 C006 1.394(4) . ?
C005 C00B 1.494(4) . ?
C005 C00C 1.386(4) . ?
C006 C009 1.510(4) . ?
C006 C00D 1.373(5) . ?
C007 H00A 0.9700 . ?
C007 H00B 0.9700 . ?
C007 C00A 1.453(5) . ?
N008 C00A 1.139(4) . ?
C009 H009 0.9800 . ?
C00B H00C 0.9800 . ?
C00C H00D 0.9300 . ?
C00C C00E 1.379(5) . ?
C00D H00E 0.9300 . ?
C00D C00F 1.406(6) . ?
C00E H00F 0.9300 . ?
C00E C00F 1.379(6) . ?
C00F H00G 0.9300 . ?

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
C009 O002 C00B 96.1(2) . . ?
I001 C003 H003 108.4 . . ?
C004 C003 I001 115.46(18) . . ?
C004 C003 H003 108.4 . . ?
C009 C003 I001 113.7(2) . . ?
C009 C003 H003 108.4 . . ?
C009 C003 C004 102.3(2) . . ?
C003 C004 H004 110.6 . . ?
C007 C004 C003 112.9(2) . . ?
C007 C004 H004 110.6 . . ?
C007 C004 C00B 111.2(2) . . ?
C00B C004 C003 100.5(2) . . ?
C00B C004 H004 110.6 . . ?
C006 C005 C00B 105.3(3) . . ?
C00C C005 C006 121.2(3) . . ?
C00C C005 C00B 133.4(3) . . ?
C005 C006 C009 104.5(3) . . ?
C00D C006 C005 121.1(3) . . ?
C00D C006 C009 134.4(3) . . ?
C004 C007 H00A 109.0 . . ?
C004 C007 H00B 109.0 . . ?
H00A C007 H00B 107.8 . . ?
C00A C007 C004 112.9(3) . . ?
C00A C007 H00A 109.0 . . ?
C00A C007 H00B 109.0 . . ?
O002 C009 C003 98.9(2) . . ?
O002 C009 C006 101.6(2) . . ?
O002 C009 H009 114.9 . . ?
C003 C009 H009 114.9 . . ?
C006 C009 C003 110.0(2) . . ?
C006 C009 H009 114.9 . . ?
N008 C00A C007 179.0(4) . . ?
O002 C00B C004 101.2(2) . . ?
O002 C00B C005 101.5(2) . . ?
O002 C00B H00C 114.9 . . ?
C004 C00B H00C 114.9 . . ?
C005 C00B C004 107.7(2) . . ?
C005 C00B H00C 114.9 . . ?
C005 C00C H00D 121.2 . . ?
C00E C00C C005 117.5(3) . . ?
C00E C00C H00D 121.2 . . ?
C006 C00D H00E 121.1 . . ?
C006 C00D C00F 117.7(4) . . ?
C00F C00D H00E 121.1 . . ?
C00C C00E H00F 119.1 . . ?
C00C C00E C00F 121.8(4) . . ?
C00F C00E H00F 119.1 . . ?
C00D C00F H00G 119.7 . . ?
C00E C00F C00D 120.6(4) . . ?
C00E C00F H00G 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
I001 C003 C004 C007 -113.0(2) . . . . ?
I001 C003 C004 C00B 128.5(2) . . . . ?
I001 C003 C009 O002 -165.24(17) . . . . ?
I001 C003 C009 C006 -59.4(3) . . . . ?
C003 C004 C007 C00A 64.4(3) . . . . ?
C003 C004 C00B O002 32.4(3) . . . . ?
C003 C004 C00B C005 -73.7(3) . . . . ?
C004 C003 C009 O002 -40.1(3) . . . . ?
C004 C003 C009 C006 65.7(3) . . . . ?
C005 C006 C009 O002 32.3(3) . . . . ?
C005 C006 C009 C003 -71.7(3) . . . . ?
C005 C006 C00D C00F -0.3(5) . . . . ?
C005 C00C C00E C00F -1.1(5) . . . . ?
C006 C005 C00B O002 -33.5(3) . . . . ?
C006 C005 C00B C004 72.3(3) . . . . ?
C006 C005 C00C C00E 1.1(4) . . . . ?
C006 C00D C00F C00E 0.3(5) . . . . ?
C007 C004 C00B O002 -87.4(3) . . . . ?
C007 C004 C00B C005 166.6(2) . . . . ?
C009 O002 C00B C004 -58.8(3) . . . . ?
C009 O002 C00B C005 52.1(3) . . . . ?
C009 C003 C004 C007 123.0(3) . . . . ?
C009 C003 C004 C00B 4.6(3) . . . . ?
C009 C006 C00D C00F -178.2(3) . . . . ?
C00B O002 C009 C003 61.1(2) . . . . ?
C00B O002 C009 C006 -51.5(2) . . . . ?
C00B C004 C007 C00A 176.5(3) . . . . ?
C00B C005 C006 C009 0.8(3) . . . . ?
C00B C005 C006 C00D -177.7(3) . . . . ?
C00B C005 C00C C00E 177.5(3) . . . . ?
C00C C005 C006 C009 178.0(3) . . . . ?
C00C C005 C006 C00D -0.4(4) . . . . ?
C00C C005 C00B O002 149.7(3) . . . . ?
C00C C005 C00B C004 -104.4(4) . . . . ?
C00C C00E C00F C00D 0.4(6) . . . . ?
C00D C006 C009 O002 -149.5(3) . . . . ?
C00D C006 C009 C003 106.5(4) . . . . ?

_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 2.238
_oxdiff_exptl_absorpt_empirical_full_min 0.582
