# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_mo220823a_pl
_database_code_depnum_ccdc_archive 'CCDC 2213685'
loop_
_audit_author_name
_audit_author_address
'Xuqiong Xiao'
;Hangzhou Normal University
China
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-08-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 I N O'
_chemical_formula_sum            'C16 H12 I N O'
_chemical_formula_weight         361.17
_chemical_absolute_configuration syn
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.896(5)
_cell_length_b                   10.615(12)
_cell_length_c                   26.62(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1383(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1944
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.550
_cell_measurement_theta_min      2.445
_shelx_estimated_absorpt_T_max   0.802
_shelx_estimated_absorpt_T_min   0.596
_exptl_absorpt_coefficient_mu    2.305
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1075 before and 0.0446 after correction.
The Ratio of minimum to maximum transmission is 0.8149.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9381
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.507
_diffrn_reflns_theta_min         1.530
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2136
_reflns_number_total             3461
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      0.997
_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)+(0.0170P)²+0.1140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0695
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.96(3)
 0.04(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C4(H4), C12(H12), C14(H14), C13(H13), C7(H7), C6(H6), C5(H5)
;
_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 0.52871(10) 0.28059(4) 0.24409(2) 0.0930(2) Uani 1 1 d . . . . .
O1 O 0.2112(7) 0.4271(3) 0.05398(12) 0.0512(9) Uani 1 1 d . . . . .
N1 N 0.3961(9) 0.6145(3) 0.03379(14) 0.0467(12) Uani 1 1 d . . . . .
C3 C 0.3803(10) 0.5406(4) -0.05387(17) 0.0398(12) Uani 1 1 d . . . . .
C2 C 0.2182(11) 0.5812(5) -0.00876(17) 0.0454(13) Uani 1 1 d . . . . .
H2 H 0.090488 0.649284 -0.016933 0.054 Uiso 1 1 calc R U . . .
C1 C 0.3781(10) 0.5254(4) 0.06475(17) 0.0412(12) Uani 1 1 d . . . . .
C11 C 0.5279(11) 0.5163(4) 0.11234(15) 0.0417(12) Uani 1 1 d . . . . .
C9 C 0.1030(12) 0.3631(5) -0.0327(2) 0.0501(15) Uani 1 1 d . . . . .
C8 C 0.3117(10) 0.4177(4) -0.06733(17) 0.0406(11) Uani 1 1 d . . . . .
C10 C 0.0688(10) 0.4614(4) 0.00790(16) 0.0476(12) Uani 1 1 d . . . . .
H10 H -0.124725 0.478406 0.014390 0.057 Uiso 1 1 calc R U . . .
C15 C 0.6218(11) 0.4202(5) 0.19122(18) 0.0517(14) Uani 1 1 d . . . . .
C16 C 0.4752(11) 0.4220(4) 0.14663(15) 0.0463(11) Uani 1 1 d . . . . .
H16 H 0.343999 0.360861 0.140000 0.056 Uiso 1 1 calc R U . . .
C4 C 0.5736(11) 0.6068(4) -0.08062(17) 0.0522(14) Uani 1 1 d . . . . .
H4 H 0.623456 0.687677 -0.070756 0.063 Uiso 1 1 calc R U . . .
C12 C 0.7233(11) 0.6063(5) 0.12296(19) 0.0544(14) Uani 1 1 d . . . . .
H12 H 0.757193 0.670615 0.100055 0.065 Uiso 1 1 calc R U . . .
C14 C 0.8178(12) 0.5088(5) 0.2013(2) 0.0588(16) Uani 1 1 d . . . . .
H14 H 0.915922 0.505730 0.231194 0.071 Uiso 1 1 calc R U . . .
C13 C 0.8675(12) 0.6015(5) 0.1671(2) 0.0661(17) Uani 1 1 d . . . . .
H13 H 1.000319 0.661886 0.173690 0.079 Uiso 1 1 calc R U . . .
C7 C 0.4323(12) 0.3647(5) -0.10909(18) 0.0584(15) Uani 1 1 d . . . . .
H7 H 0.387235 0.283220 -0.118875 0.070 Uiso 1 1 calc R U . . .
C6 C 0.6188(13) 0.4330(6) -0.1360(2) 0.0696(18) Uani 1 1 d . . . . .
H6 H 0.697529 0.397539 -0.164520 0.083 Uiso 1 1 calc R U . . .
C5 C 0.6919(13) 0.5522(6) -0.1220(2) 0.0690(17) Uani 1 1 d . . . . .
H5 H 0.821752 0.596293 -0.140471 0.083 Uiso 1 1 calc R U . . .
H9A H -0.075(11) 0.357(5) -0.0514(18) 0.063(16) Uiso 1 1 d . . . . .
H9B H 0.158(11) 0.285(5) -0.0199(18) 0.069(16) Uiso 1 1 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 C15 2.094(5) . ?
O1 C1 1.356(5) . ?
O1 C10 1.457(6) . ?
N1 C2 1.472(6) . ?
N1 C1 1.257(6) . ?
C3 C2 1.502(7) . ?
C3 C8 1.394(6) . ?
C3 C4 1.378(7) . ?
C2 H2 0.9800 . ?
C2 C10 1.532(7) . ?
C1 C11 1.467(6) . ?
C11 C16 1.379(6) . ?
C11 C12 1.382(7) . ?
C9 C8 1.494(7) . ?
C9 C10 1.511(7) . ?
C9 H9A 1.01(5) . ?
C9 H9B 0.94(5) . ?
C8 C7 1.379(6) . ?
C10 H10 0.9800 . ?
C15 C16 1.387(6) . ?
C15 C14 1.370(7) . ?
C16 H16 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.373(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(7) . ?
C14 H14 0.9300 . ?
C14 C13 1.363(8) . ?
C13 H13 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.369(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.367(8) . ?
C5 H5 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
C1 O1 C10 105.9(3) . . ?
C1 N1 C2 106.4(4) . . ?
C8 C3 C2 110.3(4) . . ?
C4 C3 C2 129.0(5) . . ?
C4 C3 C8 120.7(5) . . ?
N1 C2 C3 111.8(5) . . ?
N1 C2 H2 111.8 . . ?
N1 C2 C10 105.0(4) . . ?
C3 C2 H2 111.8 . . ?
C3 C2 C10 104.2(4) . . ?
C10 C2 H2 111.8 . . ?
O1 C1 C11 115.6(4) . . ?
N1 C1 O1 118.8(4) . . ?
N1 C1 C11 125.5(5) . . ?
C16 C11 C1 121.8(5) . . ?
C16 C11 C12 119.8(4) . . ?
C12 C11 C1 118.5(4) . . ?
C8 C9 C10 104.4(4) . . ?
C8 C9 H9A 108(3) . . ?
C8 C9 H9B 112(3) . . ?
C10 C9 H9A 108(3) . . ?
C10 C9 H9B 113(3) . . ?
H9A C9 H9B 112(4) . . ?
C3 C8 C9 111.7(4) . . ?
C7 C8 C3 119.1(5) . . ?
C7 C8 C9 129.2(5) . . ?
O1 C10 C2 102.9(4) . . ?
O1 C10 C9 112.1(4) . . ?
O1 C10 H10 111.1 . . ?
C2 C10 H10 111.1 . . ?
C9 C10 C2 108.3(4) . . ?
C9 C10 H10 111.1 . . ?
C16 C15 I1 118.2(4) . . ?
C14 C15 I1 120.4(4) . . ?
C14 C15 C16 121.4(5) . . ?
C11 C16 C15 118.7(5) . . ?
C11 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.3(5) . . ?
C5 C4 H4 120.4 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(5) . . ?
C13 C12 H12 119.8 . . ?
C15 C14 H14 120.3 . . ?
C13 C14 C15 119.3(5) . . ?
C13 C14 H14 120.3 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(5) . . ?
C14 C13 H13 119.7 . . ?
C8 C7 H7 120.3 . . ?
C6 C7 C8 119.5(5) . . ?
C6 C7 H7 120.3 . . ?
C7 C6 H6 119.3 . . ?
C5 C6 C7 121.4(6) . . ?
C5 C6 H6 119.3 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(6) . . ?
C6 C5 H5 120.0 . . ?

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 C15 C16 C11 177.7(4) . . . . ?
I1 C15 C14 C13 -177.6(4) . . . . ?
O1 C1 C11 C16 -8.0(7) . . . . ?
O1 C1 C11 C12 173.0(4) . . . . ?
N1 C2 C10 O1 -9.6(5) . . . . ?
N1 C2 C10 C9 -128.3(5) . . . . ?
N1 C1 C11 C16 173.0(5) . . . . ?
N1 C1 C11 C12 -5.9(7) . . . . ?
C3 C2 C10 O1 108.1(4) . . . . ?
C3 C2 C10 C9 -10.7(5) . . . . ?
C3 C8 C7 C6 0.8(7) . . . . ?
C3 C4 C5 C6 -0.4(8) . . . . ?
C2 N1 C1 O1 -0.9(6) . . . . ?
C2 N1 C1 C11 178.0(5) . . . . ?
C2 C3 C8 C9 -1.0(6) . . . . ?
C2 C3 C8 C7 177.8(4) . . . . ?
C2 C3 C4 C5 -178.0(5) . . . . ?
C1 O1 C10 C2 9.1(5) . . . . ?
C1 O1 C10 C9 125.2(4) . . . . ?
C1 N1 C2 C3 -105.6(5) . . . . ?
C1 N1 C2 C10 6.7(5) . . . . ?
C1 C11 C16 C15 -179.0(5) . . . . ?
C1 C11 C12 C13 179.8(5) . . . . ?
C11 C12 C13 C14 -0.8(9) . . . . ?
C9 C8 C7 C6 179.3(5) . . . . ?
C8 C3 C2 N1 120.1(4) . . . . ?
C8 C3 C2 C10 7.2(5) . . . . ?
C8 C3 C4 C5 2.3(7) . . . . ?
C8 C9 C10 O1 -102.7(4) . . . . ?
C8 C9 C10 C2 10.1(5) . . . . ?
C8 C7 C6 C5 1.1(8) . . . . ?
C10 O1 C1 N1 -5.7(6) . . . . ?
C10 O1 C1 C11 175.3(4) . . . . ?
C10 C9 C8 C3 -5.8(6) . . . . ?
C10 C9 C8 C7 175.6(5) . . . . ?
C15 C14 C13 C12 0.0(9) . . . . ?
C16 C11 C12 C13 0.9(8) . . . . ?
C16 C15 C14 C13 0.8(8) . . . . ?
C4 C3 C2 N1 -59.6(6) . . . . ?
C4 C3 C2 C10 -172.5(5) . . . . ?
C4 C3 C8 C9 178.7(4) . . . . ?
C4 C3 C8 C7 -2.5(7) . . . . ?
C12 C11 C16 C15 -0.1(7) . . . . ?
C14 C15 C16 C11 -0.7(8) . . . . ?
C7 C6 C5 C4 -1.3(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.96(3)
2 0.04(3)

