# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_tch205m
_database_code_depnum_ccdc_archive 'CCDC 2128396'
loop_
_audit_author_name
_audit_author_address
'Yong Xin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 I N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         286.11

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   6.7210(3)
_cell_length_b                   19.9988(11)
_cell_length_c                   32.6212(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4384.7(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9699
_cell_measurement_theta_min      2.3891
_cell_measurement_theta_max      25.9563
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2208

_exptl_absorpt_coefficient_mu    2.880
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            30171
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         27.14
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41

_refine_special_details          
;
;

_reflns_number_total             1221
_reflns_number_gt                946
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0965
_refine_ls_wR_factor_gt          0.2711
_refine_ls_wR_factor_ref         0.2879
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.086
_refine_ls_number_reflns         1221
_refine_ls_number_parameters     91
_refine_ls_number_restraints     188
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1293P)²+178.9953P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.555
_refine_diff_density_min         -1.496
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.390(2) 0.6980(9) 0.5466(5) 0.055(4) Uani d U P D 0.5 A -1
H H1A 0.393721 0.740962 0.552414 0.066000 Uiso calc U P R 0.5 A -1
H H1B 0.390474 0.684693 0.520906 0.066000 Uiso calc U P R 0.5 A -1
C C1 0.3695(19) 0.5514(4) 0.6398(3) 0.060(3) Uani d U P G 0.5 A -1
H H1 0.365355 0.517916 0.660454 0.072000 Uiso calc U P R 0.5 A -1
N N2 0.3712(18) 0.5332(4) 0.5987(3) 0.060(3) Uani d U P G 0.5 A -1
C C3 0.3772(18) 0.5821(5) 0.5685(3) 0.060(3) Uani d U P DG 0.5 A -1
H H3 0.378323 0.569654 0.540357 0.072000 Uiso calc U P R 0.5 A -1
C C4 0.3815(19) 0.6493(5) 0.5794(2) 0.058(3) Uani d U P G 0.5 A -1
C C5 0.3798(12) 0.6675(4) 0.6205(2) 0.055(3) Uani d U P DG 0.5 A -1
C C6 0.3738(12) 0.6186(4) 0.6507(2) 0.057(3) Uani d U P G 0.5 A -1
C C7 0.372(2) 0.6368(6) 0.6918(2) 0.066(3) Uani d U P G 0.5 A -1
H H7 0.367954 0.603313 0.712469 0.079000 Uiso calc U P R 0.5 A -1
C C8 0.376(2) 0.7039(7) 0.7027(3) 0.066(4) Uani d U P G 0.5 A -1
H H8 0.375193 0.716402 0.730815 0.080000 Uiso calc U P R 0.5 A -1
C C9 0.382(2) 0.7529(5) 0.6725(4) 0.061(3) Uani d U P G 0.5 A -1
H H9 0.385296 0.798818 0.679940 0.073000 Uiso calc U P R 0.5 A -1
C C10 0.384(2) 0.7347(4) 0.6314(3) 0.062(3) Uani d U P G 0.5 A -1
H H10 0.388161 0.768146 0.610718 0.074000 Uiso calc U P R 0.5 A -1
C C11 0.366(4) 0.4652(15) 0.5863(11) 0.081(6) Uani d U P . 0.5 A -1
H H11A 0.297495 0.461445 0.559945 0.121000 Uiso calc U P R 0.5 A -1
H H11B 0.295218 0.438748 0.606986 0.121000 Uiso calc U P R 0.5 A -1
H H11C 0.502499 0.448351 0.583573 0.121000 Uiso calc U P R 0.5 A -1
I I1 0.375000 0.375000 0.70566(4) 0.0806(6) Uani d TU P S 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C4 . 1.447(19) ?
C1 N2 . 1.390000 ?
C1 C6 . 1.390000 ?
N2 C3 . 1.390000 ?
N2 C11 . 1.42(3) ?
C3 C4 . 1.390000 ?
C4 C5 . 1.390000 ?
C5 C6 . 1.390000 ?
C5 C10 . 1.390000 ?
C6 C7 . 1.390000 ?
C7 C8 . 1.390000 ?
C8 C9 . 1.390000 ?
C9 C10 . 1.390000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C6 . . 120.000000 ?
C1 N2 C3 . . 120.000000 ?
C1 N2 C11 . . 121.7(16) ?
C3 N2 C11 . . 118.3(16) ?
N2 C3 C4 . . 120.000000 ?
C5 C4 C3 . . 120.000000 ?
C5 C4 N1 . . 122.4(6) ?
C3 C4 N1 . . 117.6(6) ?
C4 C5 C6 . . 120.000000 ?
C4 C5 C10 . . 120.000000 ?
C6 C5 C10 . . 120.000000 ?
C7 C6 C5 . . 120.000000 ?
C7 C6 C1 . . 120.000000 ?
C5 C6 C1 . . 120.000000 ?
C6 C7 C8 . . 120.000000 ?
C7 C8 C9 . . 120.000000 ?
C8 C9 C10 . . 120.000000 ?
C9 C10 C5 . . 120.000000 ?

####################################################################### 
# 
# 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_tch208m
_database_code_depnum_ccdc_archive 'CCDC 2128397'
loop_
_audit_author_name
_audit_author_address
'Yong Xin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H15.25 Br N2 O0.12'
_chemical_formula_iupac          ?
_chemical_formula_weight         269.42

_chemical_melting_point          ?

_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                   15.3346(6)
_cell_length_b                   15.1704(6)
_cell_length_c                   10.1934(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.8457(16)
_cell_angle_gamma                90
_cell_volume                     2370.08(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      2.6853
_cell_measurement_theta_max      30.3430
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1098

_exptl_absorpt_coefficient_mu    3.440
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.72

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            84482
_diffrn_reflns_av_R_equivalents  0.1252
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             7235
_reflns_number_gt                4665
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.1067
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_number_reflns         7235
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+4.5453P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.298
_refine_diff_density_min         -0.577
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Br Br -0.2901 2.4595 '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'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.84156(2) 0.41905(2) 0.09217(3) 0.02300(9) Uani d . . . 1 . .
Br Br2 0.66185(2) 0.42226(2) 0.60116(3) 0.02448(9) Uani d . . . 1 . .
C C1 0.8532(2) 0.6931(2) 1.0147(4) 0.0289(8) Uani d . . . 1 . .
H H1A 0.819969 0.643235 1.048382 0.043000 Uiso calc U . R 1 . .
H H1B 0.823519 0.748313 1.035747 0.043000 Uiso calc U . R 1 . .
H H1C 0.911938 0.693155 1.055373 0.043000 Uiso calc U . R 1 . .
C C2 0.8594(2) 0.6847(2) 0.8662(3) 0.0255(7) Uani d . . . 1 . .
H H2A 0.800098 0.681235 0.825343 0.031000 Uiso calc U . R 1 . .
H H2B 0.888683 0.737435 0.831062 0.031000 Uiso calc U . R 1 . .
C C3 0.9108(2) 0.6025(2) 0.8321(3) 0.0232(7) Uani d . . . 1 . .
H H3A 0.967421 0.602761 0.881538 0.028000 Uiso calc U . R 1 . .
H H3B 0.878011 0.549511 0.858502 0.028000 Uiso calc U . R 1 . .
C C4 0.9979(2) 0.6358(2) 0.6451(3) 0.0230(7) Uani d . . . 1 . .
H H4 1.038499 0.663015 0.704648 0.028000 Uiso calc U . R 1 . .
C C5 1.0134(2) 0.6348(2) 0.5094(3) 0.0225(7) Uani d . . . 1 . .
C C6 1.0891(2) 0.6748(2) 0.4606(4) 0.0287(8) Uani d . . . 1 . .
H H6 1.128705 0.704366 0.519081 0.034000 Uiso calc U . R 1 . .
C C7 1.1054(2) 0.6713(2) 0.3302(4) 0.0295(8) Uani d . . . 1 . .
H H7 1.156749 0.697786 0.298296 0.035000 Uiso calc U . R 1 . .
C C8 1.0467(2) 0.6288(2) 0.2428(4) 0.0274(7) Uani d . . . 1 . .
H H8 1.058730 0.626474 0.152003 0.033000 Uiso calc U . R 1 . .
C C9 0.9716(2) 0.5902(2) 0.2873(3) 0.0229(7) Uani d . . . 1 . .
H H9 0.932205 0.562119 0.226892 0.027000 Uiso calc U . R 1 . .
C C10 0.9532(2) 0.59232(19) 0.4215(3) 0.0216(7) Uani d . . . 1 . .
C C11 0.8763(2) 0.5534(2) 0.4750(3) 0.0191(6) Uani d . . . 1 . .
C C12 0.8654(2) 0.5586(2) 0.6082(3) 0.0197(6) Uani d . . . 1 . .
H H12 0.814571 0.534058 0.644680 0.024000 Uiso calc U . R 1 . .
C C13 0.6427(2) 0.6923(2) 0.5223(4) 0.0287(8) Uani d . . . 1 . .
H H13A 0.583719 0.692385 0.556392 0.043000 Uiso calc U . R 1 . .
H H13B 0.672445 0.747248 0.547136 0.043000 Uiso calc U . R 1 . .
H H13C 0.675504 0.642104 0.559126 0.043000 Uiso calc U . R 1 . .
C C14 0.6374(2) 0.6845(2) 0.3734(3) 0.0250(7) Uani d . . . 1 . .
H H14A 0.696915 0.680609 0.339067 0.030000 Uiso calc U . R 1 . .
H H14B 0.608892 0.737715 0.335423 0.030000 Uiso calc U . R 1 . .
C C15 0.5854(2) 0.6029(2) 0.3327(3) 0.0219(7) Uani d . . . 1 . .
H H15A 0.617901 0.549509 0.361123 0.026000 Uiso calc U . R 1 . .
H H15B 0.528876 0.603133 0.377038 0.026000 Uiso calc U . R 1 . .
C C16 0.4964(2) 0.6355(2) 0.1382(4) 0.0240(7) Uani d . . . 1 . .
H H16 0.455015 0.661056 0.194236 0.029000 Uiso calc U . R 1 . .
C C17 0.4808(2) 0.6350(2) 0.0019(4) 0.0250(7) Uani d . . . 1 . .
C C18 0.4034(2) 0.6730(2) -0.0535(4) 0.0298(8) Uani d . . . 1 . .
H H18 0.362983 0.701047 0.001513 0.036000 Uiso calc U . R 1 . .
C C19 0.3872(2) 0.6693(2) -0.1854(4) 0.0322(9) Uani d . . . 1 . .
H H19 0.335054 0.694297 -0.222043 0.039000 Uiso calc U . R 1 . .
C C20 0.4470(2) 0.6287(2) -0.2677(4) 0.0297(8) Uani d . . . 1 . .
H H20 0.434746 0.626399 -0.359615 0.036000 Uiso calc U . R 1 . .
C C21 0.5235(2) 0.5919(2) -0.2168(3) 0.0243(7) Uani d . . . 1 . .
H H21 0.563464 0.564801 -0.273513 0.029000 Uiso calc U . R 1 . .
C C22 0.5418(2) 0.59495(19) -0.0801(3) 0.0203(6) Uani d . . . 1 . .
C C23 0.6200(2) 0.5577(2) -0.0214(3) 0.0208(7) Uani d . . . 1 . .
C C24 0.6311(2) 0.5621(2) 0.1139(3) 0.0217(7) Uani d . . . 1 . .
H H24 0.682348 0.538275 0.154973 0.026000 Uiso calc U . R 1 . .
N N1 0.92645(17) 0.59845(16) 0.6891(3) 0.0198(6) Uani d . . . 1 . .
N N2 0.81422(17) 0.51322(18) 0.3971(3) 0.0230(6) Uani d . . . 1 . .
H H2C 0.767457 0.490733 0.432108 0.028000 Uiso calc U . R 1 . .
H H2D 0.820928 0.509762 0.311846 0.028000 Uiso calc U . R 1 . .
N N3 0.56933(17) 0.60009(17) 0.1890(3) 0.0214(6) Uani d . . . 1 . .
N N4 0.68278(18) 0.52020(19) -0.0945(3) 0.0251(6) Uani d . . . 1 . .
H H4A 0.730353 0.498791 -0.055879 0.030000 Uiso calc U . R 1 . .
H H4B 0.675817 0.517383 -0.180460 0.030000 Uiso calc U . R 1 . .
O O1 0.2558(6) 0.6996(6) 0.1438(9) 0.025(2) Uani d . P . 0.25 . .
H H1O 0.244269 0.755267 0.117586 0.038000 Uiso d U P R 0.25 . .
H H2O 0.234807 0.659455 0.085804 0.038000 Uiso d U P R 0.25 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.525(5) ?
C2 C3 . 1.521(4) ?
C3 N1 . 1.486(4) ?
C4 N1 . 1.324(4) ?
C4 C5 . 1.412(5) ?
C5 C6 . 1.413(5) ?
C5 C10 . 1.421(5) ?
C6 C7 . 1.361(5) ?
C7 C8 . 1.404(5) ?
C8 C9 . 1.381(5) ?
C9 C10 . 1.406(5) ?
C10 C11 . 1.441(4) ?
C11 N2 . 1.364(4) ?
C11 C12 . 1.376(5) ?
C12 N1 . 1.368(4) ?
C13 C14 . 1.522(5) ?
C14 C15 . 1.522(4) ?
C15 N3 . 1.479(4) ?
C16 N3 . 1.330(4) ?
C16 C17 . 1.402(5) ?
C17 C22 . 1.412(5) ?
C17 C18 . 1.419(5) ?
C18 C19 . 1.361(5) ?
C19 C20 . 1.405(6) ?
C20 C21 . 1.384(5) ?
C21 C22 . 1.413(5) ?
C22 C23 . 1.438(4) ?
C23 N4 . 1.361(4) ?
C23 C24 . 1.386(5) ?
C24 N3 . 1.364(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C2 C1 . . 110.2(3) ?
N1 C3 C2 . . 111.1(3) ?
N1 C4 C5 . . 119.7(3) ?
C4 C5 C6 . . 120.5(3) ?
C4 C5 C10 . . 119.7(3) ?
C6 C5 C10 . . 119.8(3) ?
C7 C6 C5 . . 120.4(3) ?
C6 C7 C8 . . 120.2(3) ?
C9 C8 C7 . . 120.7(3) ?
C8 C9 C10 . . 120.4(3) ?
C9 C10 C5 . . 118.5(3) ?
C9 C10 C11 . . 123.5(3) ?
C5 C10 C11 . . 118.1(3) ?
N2 C11 C12 . . 119.7(3) ?
N2 C11 C10 . . 121.8(3) ?
C12 C11 C10 . . 118.5(3) ?
N1 C12 C11 . . 121.1(3) ?
C13 C14 C15 . . 110.2(3) ?
N3 C15 C14 . . 111.2(3) ?
N3 C16 C17 . . 119.9(3) ?
C16 C17 C22 . . 119.5(3) ?
C16 C17 C18 . . 120.4(3) ?
C22 C17 C18 . . 120.0(3) ?
C19 C18 C17 . . 120.1(4) ?
C18 C19 C20 . . 120.4(3) ?
C21 C20 C19 . . 120.9(3) ?
C20 C21 C22 . . 119.7(3) ?
C17 C22 C21 . . 118.9(3) ?
C17 C22 C23 . . 118.8(3) ?
C21 C22 C23 . . 122.3(3) ?
N4 C23 C24 . . 119.9(3) ?
N4 C23 C22 . . 122.1(3) ?
C24 C23 C22 . . 118.0(3) ?
N3 C24 C23 . . 120.9(3) ?
C4 N1 C12 . . 122.9(3) ?
C4 N1 C3 . . 118.4(3) ?
C12 N1 C3 . . 118.7(3) ?
C16 N3 C24 . . 122.9(3) ?
C16 N3 C15 . . 119.0(3) ?
C24 N3 C15 . . 118.1(3) ?

####################################################################### 
# 
# 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_tch206m
_database_code_depnum_ccdc_archive 'CCDC 2128398'
loop_
_audit_author_name
_audit_author_address
'Yong Xin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 I N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         220.01

_chemical_melting_point          ?

_space_group_crystal_system      tetragonal
_space_group_IT_number           139
_space_group_name_H-M_alt        'I 4/m m m'
_space_group_name_Hall           '-I 4 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'-x, y, -z'
'x, -y, -z'
'y, x, -z'
'-y, -x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y+1/2, x+1/2, -z+1/2'
'-y+1/2, -x+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'x, -y, z'
'-x, y, z'
'-y, -x, z'
'y, x, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   10.3872(3)
_cell_length_b                   10.3872(3)
_cell_length_c                   13.2209(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1426.45(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9194
_cell_measurement_theta_min      2.4936
_cell_measurement_theta_max      44.0853
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_crystal_density_diffrn    2.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816

_exptl_absorpt_coefficient_mu    4.391
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.17
_exptl_absorpt_correction_T_max  0.45

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            24275
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         53.91
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       30

_refine_special_details          
;
;

_reflns_number_total             2491
_reflns_number_gt                1838
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0942
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.014
_refine_ls_number_reflns         2491
_refine_ls_number_parameters     46
_refine_ls_number_restraints     88
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+3.0864P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.298
_refine_diff_density_min         -1.762
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5258(3) 0.2098(4) 0.5021(11) 0.0202(7) Uani d U P D 0.25 A -1
H H1A 0.495414 0.188867 0.570336 0.030000 Uiso calc U P R 0.25 A -1
H H1B 0.494988 0.144378 0.454448 0.030000 Uiso calc U P R 0.25 A -1
H H1C 0.492588 0.294343 0.482132 0.030000 Uiso calc U P R 0.25 A -1
N N1 0.93250(14) 0.2171(3) 0.4983(6) 0.0189(5) Uani d U P G 0.25 A -1
C C2 0.8670(5) 0.2248(5) 0.5898(4) 0.0171(5) Uani d U P G 0.25 A -1
H H2 0.913699 0.231628 0.651384 0.020000 Uiso calc U P R 0.25 A -1
C C3 0.7332(5) 0.2223(5) 0.5913(4) 0.0143(5) Uani d U P DG 0.25 A -1
H H3 0.688481 0.227515 0.653789 0.017000 Uiso calc U P R 0.25 A -1
N N2 0.66493(14) 0.2123(2) 0.5012(5) 0.0149(4) Uani d U P G 0.25 A -1
C C4 0.7304(5) 0.2046(5) 0.4097(4) 0.0143(5) Uani d U P DG 0.25 A -1
H H4 0.683734 0.197778 0.348144 0.017000 Uiso calc U P R 0.25 A -1
C C5 0.8642(5) 0.2071(5) 0.4083(4) 0.0171(5) Uani d U P G 0.25 A -1
H H5 0.908952 0.201891 0.345737 0.020000 Uiso calc U P R 0.25 A -1
I I1 0.500000 0.000000 0.250000 0.01766(5) Uani d T P S 1 . .
I I2 0.500000 0.500000 0.69070(2) 0.02006(5) Uani d T P S 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.446(4) ?
N1 C2 . 1.390000 ?
N1 C5 . 1.390000 ?
C2 C3 . 1.390000 ?
C3 N2 . 1.390000 ?
N2 C4 . 1.390000 ?
C4 C5 . 1.390000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 . . 120.000000 ?
C3 C2 N1 . . 120.000000 ?
C2 C3 N2 . . 120.000000 ?
C3 N2 C4 . . 120.000000 ?
C3 N2 C1 . . 120.3(4) ?
C4 N2 C1 . . 119.7(4) ?
C5 C4 N2 . . 120.000000 ?
C4 C5 N1 . . 120.000000 ?

####################################################################### 
# 
# 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_tch207m
_database_code_depnum_ccdc_archive 'CCDC 2128399'
loop_
_audit_author_name
_audit_author_address
'Yong Xin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H7 I2 N3'
_chemical_formula_iupac          ?
_chemical_formula_weight         362.94
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_cell_length_a                   7.0916(2)
_cell_length_b                   7.0916(2)
_cell_length_c                   31.4164(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1368.28(10)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    8247
_cell_measurement_theta_min      3.3171
_cell_measurement_theta_max      33.5527
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.005
_exptl_crystal_density_diffrn    2.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984

_exptl_absorpt_coefficient_mu    6.832
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            20272
_diffrn_reflns_av_R_equivalents  0.1235
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         33.72
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       49

_refine_special_details          
;

Refined as a 3-component twin.
;

_reflns_number_total             3262
_reflns_number_gt                2598
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_max     0.813
_reflns_Friedel_fraction_full    1.000

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0682
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_number_reflns         3262
_refine_ls_number_parameters     94
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0080P)²+3.9345P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.339
_refine_diff_density_min         -1.267
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 942 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(4)

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'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1162(16) 0.5488(16) 0.4510(3) 0.0166(19) Uani d . . . 1 . .
H H1 0.165775 0.659905 0.430033 0.020000 Uiso calc U . R 1 . .
C C2 0.1596(14) 0.6134(15) 0.4937(3) 0.0156(18) Uani d . . . 1 . .
C C3 -0.0236(14) 0.2437(17) 0.5111(3) 0.0155(18) Uani d . . . 1 . .
H H3 -0.076493 0.132738 0.532177 0.019000 Uiso calc U . R 1 . .
C C4 -0.0609(16) 0.1884(17) 0.4678(3) 0.0179(19) Uani d . . . 1 . .
C C5 0.1253(17) 0.5062(17) 0.5687(3) 0.019(2) Uani d . . . 1 . .
H H5A 0.049425 0.583343 0.577566 0.028000 Uiso calc U . R 1 . .
H H5B 0.281853 0.598869 0.573858 0.028000 Uiso calc U . R 1 . .
H H5C 0.070213 0.371337 0.585185 0.028000 Uiso calc U . R 1 . .
I I1 0.32309(10) 0.94439(10) 0.50772(2) 0.01770(13) Uani d . . . 1 . .
I I2 0.61235(10) 0.50322(10) 0.52224(2) 0.01538(12) Uani d . . . 1 . .
N N1 0.0117(13) 0.3449(13) 0.4379(2) 0.0185(17) Uani d . . . 1 . .
N N2 0.0866(12) 0.4531(13) 0.5226(2) 0.0146(15) Uani d . . . 1 . .
N N3 -0.1695(14) -0.0200(14) 0.4545(3) 0.0224(19) Uani d . . . 1 . .
H H3A -0.190584 -0.049400 0.427087 0.027000 Uiso calc U . R 1 . .
H H3B -0.219447 -0.126735 0.473134 0.027000 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.319(12) ?
C1 C2 . 1.400(12) ?
C2 N2 . 1.341(12) ?
C2 I1 . 2.080(9) ?
C3 N2 . 1.336(13) ?
C3 C4 . 1.405(13) ?
C4 N1 . 1.346(12) ?
C4 N3 . 1.347(13) ?
C5 N2 . 1.488(12) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 124.8(9) ?
N2 C2 C1 . . 116.3(8) ?
N2 C2 I1 . . 125.0(7) ?
C1 C2 I1 . . 118.6(7) ?
N2 C3 C4 . . 119.8(9) ?
N1 C4 N3 . . 117.4(8) ?
N1 C4 C3 . . 120.4(9) ?
N3 C4 C3 . . 122.2(9) ?
C1 N1 C4 . . 117.3(8) ?
C3 N2 C2 . . 121.5(8) ?
C3 N2 C5 . . 118.4(8) ?
C2 N2 C5 . . 120.1(8) ?

####################################################################### 
# 
# 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_tch214m
_database_code_depnum_ccdc_archive 'CCDC 2128400'
loop_
_audit_author_name
_audit_author_address
'Yong Xin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 I3 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         597.94
_chemical_absolute_configuration ?

_chemical_melting_point          ?

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

_cell_length_a                   8.2027(3)
_cell_length_b                   13.5124(4)
_cell_length_c                   14.3668(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1592.39(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9997
_cell_measurement_theta_min      2.8595
_cell_measurement_theta_max      38.5226
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    2.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096

_exptl_absorpt_coefficient_mu    5.888
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_T_max  0.54

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CMOS detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            42531
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         43.26
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             11862
_reflns_number_gt                8782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.999

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_gt          0.0500
_refine_ls_wR_factor_ref         0.0557
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_number_reflns         11862
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0135P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.411
_refine_diff_density_min         -1.498
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 3072 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(15)

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'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2467(5) 0.5408(3) 0.9498(3) 0.0207(8) Uani d . . . 1 . .
H H1A 0.255497 0.522896 1.015677 0.031000 Uiso calc U . R 1 . .
H H1B 0.132240 0.537421 0.930418 0.031000 Uiso calc U . R 1 . .
H H1C 0.287630 0.608209 0.940623 0.031000 Uiso calc U . R 1 . .
C C2 0.4224(4) 0.3964(3) 0.9385(3) 0.0169(7) Uani d . . . 1 . .
H H2 0.411735 0.389752 1.004002 0.020000 Uiso calc U . R 1 . .
C C3 0.5169(4) 0.3304(3) 0.8890(3) 0.0168(7) Uani d . . . 1 . .
H H3 0.574667 0.279581 0.920707 0.020000 Uiso calc U . R 1 . .
C C4 0.5275(4) 0.3383(3) 0.7934(2) 0.0153(6) Uani d . . . 1 . .
H H4 0.595749 0.293975 0.760095 0.018000 Uiso calc U . R 1 . .
C C5 0.4392(4) 0.4107(2) 0.7443(2) 0.0126(6) Uani d . . . 1 . .
C C6 0.3488(4) 0.4784(2) 0.7988(2) 0.0114(6) Uani d . . . 1 . .
C C7 0.2259(5) -0.0358(3) 0.4499(3) 0.0179(7) Uani d . . . 1 . .
H H7A 0.179770 -0.094802 0.479501 0.027000 Uiso calc U . R 1 . .
H H7B 0.327559 -0.053386 0.418095 0.027000 Uiso calc U . R 1 . .
H H7C 0.147976 -0.009431 0.404458 0.027000 Uiso calc U . R 1 . .
C C8 0.2046(4) 0.0224(3) 0.6091(2) 0.0149(6) Uani d . . . 1 . .
H H8 0.150907 -0.038178 0.622747 0.018000 Uiso calc U . R 1 . .
C C9 0.2260(4) 0.0913(3) 0.6776(2) 0.0169(6) Uani d . . . 1 . .
H H9 0.185930 0.078951 0.738576 0.020000 Uiso calc U . R 1 . .
C C10 0.3065(4) 0.1796(3) 0.6581(2) 0.0149(6) Uani d . . . 1 . .
H H10 0.319274 0.228231 0.705296 0.018000 Uiso calc U . R 1 . .
C C11 0.3684(4) 0.1964(2) 0.5691(2) 0.0125(6) Uani d . . . 1 . .
C C12 0.3418(4) 0.1250(2) 0.5003(2) 0.0122(6) Uani d . . . 1 . .
I I1 0.21978(3) 0.59063(2) 0.73163(2) 0.01376(4) Uani d . . . 1 . .
I I2 0.42220(3) 0.15261(2) 0.36475(2) 0.01447(4) Uani d . . . 1 . .
I I3 0.52947(3) 0.22269(2) 0.13987(2) 0.01322(4) Uani d . . . 1 . .
N N1 0.3445(3) 0.4709(2) 0.8932(2) 0.0144(5) Uani d . . . 1 . .
N N2 0.2596(4) 0.0402(2) 0.5217(2) 0.0134(5) Uani d . . . 1 . .
O O1 0.4352(3) 0.41752(18) 0.65474(17) 0.0161(5) Uani d . . . 1 . .
O O2 0.4529(3) 0.27664(18) 0.54643(18) 0.0189(5) Uani d . . . 1 . .
H H2A 0.446997 0.318163 0.589812 0.028000 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.482(5) ?
C2 N1 . 1.359(5) ?
C2 C3 . 1.378(5) ?
C3 C4 . 1.381(5) ?
C4 C5 . 1.406(5) ?
C5 O1 . 1.291(4) ?
C5 C6 . 1.414(4) ?
C6 N1 . 1.360(4) ?
C6 I1 . 2.086(3) ?
C7 N2 . 1.482(4) ?
C8 N2 . 1.356(4) ?
C8 C9 . 1.366(5) ?
C9 C10 . 1.392(5) ?
C10 C11 . 1.394(5) ?
C11 O2 . 1.327(4) ?
C11 C12 . 1.399(5) ?
C12 N2 . 1.364(4) ?
C12 I2 . 2.090(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C2 C3 . . 119.8(3) ?
C2 C3 C4 . . 119.8(3) ?
C3 C4 C5 . . 121.4(3) ?
O1 C5 C4 . . 124.2(3) ?
O1 C5 C6 . . 119.5(3) ?
C4 C5 C6 . . 116.3(3) ?
N1 C6 C5 . . 121.1(3) ?
N1 C6 I1 . . 120.1(2) ?
C5 C6 I1 . . 118.7(2) ?
N2 C8 C9 . . 120.2(3) ?
C8 C9 C10 . . 120.0(3) ?
C9 C10 C11 . . 119.8(3) ?
O2 C11 C10 . . 123.3(3) ?
O2 C11 C12 . . 118.1(3) ?
C10 C11 C12 . . 118.6(3) ?
N2 C12 C11 . . 119.9(3) ?
N2 C12 I2 . . 121.0(2) ?
C11 C12 I2 . . 119.1(2) ?
C2 N1 C6 . . 121.4(3) ?
C2 N1 C1 . . 117.6(3) ?
C6 N1 C1 . . 120.9(3) ?
C8 N2 C12 . . 121.4(3) ?
C8 N2 C7 . . 117.4(3) ?
C12 N2 C7 . . 121.2(3) ?

####################################################################### 
# 
# 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_tch218m
_database_code_depnum_ccdc_archive 'CCDC 2142749'
loop_
_audit_author_name
_audit_author_address
'Yong Xin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2022-01-18 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 I N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         304.12

_chemical_melting_point          ?

_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                   7.3757(6)
_cell_length_b                   19.8901(17)
_cell_length_c                   8.6493(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.402(3)
_cell_angle_gamma                90
_cell_volume                     1155.53(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      2.7814
_cell_measurement_theta_max      34.1384
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592

_exptl_absorpt_coefficient_mu    2.743
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CMOS detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            49445
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         39.47
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             6893
_reflns_number_gt                4907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0727
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.049
_refine_ls_number_reflns         6893
_refine_ls_number_parameters     134
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0258P)²+0.3782P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.164
_refine_diff_density_min         -1.226
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.9938(3) 0.69016(10) 0.6124(3) 0.0320(4) Uani d . . . 1 . .
H H1A 0.960353 0.731164 0.543433 0.048000 Uiso calc U . R 1 . .
H H1B 1.133110 0.678246 0.642063 0.048000 Uiso calc U . R 1 . .
H H1C 0.974270 0.697864 0.716423 0.048000 Uiso calc U . R 1 . .
C C2 0.7262(3) 0.64667(9) 0.3589(3) 0.0270(4) Uani d . . . 1 . .
H H2 0.716619 0.690394 0.312000 0.032000 Uiso calc U . R 1 . .
C C3 0.5973(3) 0.59722(10) 0.2636(2) 0.0268(4) Uani d . . . 1 . .
H H3 0.501333 0.606679 0.152115 0.032000 Uiso calc U . R 1 . .
C C4 0.6095(3) 0.53418(10) 0.3318(2) 0.0235(3) Uani d . . . 1 . .
H H4 0.521136 0.499837 0.267203 0.028000 Uiso calc U . R 1 . .
C C5 0.7524(2) 0.52008(9) 0.4971(2) 0.0205(3) Uani d . . . 1 . .
C C6 0.8832(2) 0.57217(9) 0.5894(2) 0.0209(3) Uani d . . . 1 . .
C C7 1.0295(3) 0.55896(9) 0.7537(2) 0.0237(3) Uani d . . . 1 . .
H H7 1.119653 0.593237 0.816186 0.028000 Uiso calc U . R 1 . .
C C8 1.0404(3) 0.49638(10) 0.8225(2) 0.0246(3) Uani d . . . 1 . .
H H8 1.140132 0.487882 0.933032 0.029000 Uiso calc U . R 1 . .
C C9 0.9080(3) 0.44356(9) 0.7345(2) 0.0228(3) Uani d . . . 1 . .
C C10 0.7671(3) 0.45628(9) 0.5712(2) 0.0215(3) Uani d . . . 1 . .
H H10 0.679461 0.421404 0.508733 0.026000 Uiso calc U . R 1 . .
I I1 0.39313(2) 0.15608(2) 0.67286(2) 0.02251(4) Uani d . . . 1 . .
N N1 0.8637(2) 0.63477(8) 0.5150(2) 0.0238(3) Uani d . . . 1 . .
N N2 0.9178(2) 0.38317(9) 0.8122(2) 0.0302(3) Uani d . . . 1 . .
H H2A 0.833244 0.350972 0.758682 0.036000 Uiso calc U . R 1 . .
H H2B 1.008572 0.376395 0.915835 0.036000 Uiso calc U . R 1 . .
O O1 0.6925(2) 0.27323(9) 0.5763(2) 0.0417(4) Uani d . . D 1 . .
H H2O 0.616(4) 0.2916(14) 0.475(3) 0.063000 Uiso d U . D 1 . .
H H1O 0.620(4) 0.2433(12) 0.607(3) 0.063000 Uiso d U . D 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.475(3) ?
C2 N1 . 1.333(3) ?
C2 C3 . 1.379(3) ?
C3 C4 . 1.373(3) ?
C4 C5 . 1.410(2) ?
C5 C10 . 1.406(2) ?
C5 C6 . 1.416(2) ?
C6 N1 . 1.381(2) ?
C6 C7 . 1.409(3) ?
C7 C8 . 1.367(3) ?
C8 C9 . 1.423(3) ?
C9 N2 . 1.364(2) ?
C9 C10 . 1.387(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C2 C3 . . 121.80(17) ?
C4 C3 C2 . . 119.21(18) ?
C3 C4 C5 . . 120.40(18) ?
C10 C5 C4 . . 121.77(17) ?
C10 C5 C6 . . 119.80(16) ?
C4 C5 C6 . . 118.43(16) ?
N1 C6 C7 . . 121.80(16) ?
N1 C6 C5 . . 118.75(16) ?
C7 C6 C5 . . 119.45(16) ?
C8 C7 C6 . . 119.45(17) ?
C7 C8 C9 . . 122.36(17) ?
N2 C9 C10 . . 121.81(17) ?
N2 C9 C8 . . 120.13(17) ?
C10 C9 C8 . . 118.04(17) ?
C9 C10 C5 . . 120.87(17) ?
C2 N1 C6 . . 121.41(16) ?
C2 N1 C1 . . 119.28(17) ?
C6 N1 C1 . . 119.28(17) ?

####################################################################### 
# 
# 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_tch216m
_database_code_depnum_ccdc_archive 'CCDC 2128401'
loop_
_audit_author_name
_audit_author_address
'Yong Xin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 I N S'
_chemical_formula_iupac          ?
_chemical_formula_weight         253.09

_chemical_melting_point          ?

_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                   6.9824(9)
_cell_length_b                   15.4554(19)
_cell_length_c                   7.8105(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.042(7)
_cell_angle_gamma                90
_cell_volume                     842.74(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6628
_cell_measurement_theta_min      2.9178
_cell_measurement_theta_max      35.3796
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.995
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    3.966
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.69

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CMOS detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            26220
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0920
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         43.06
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             6236
_reflns_number_gt                3762
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0693
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_refine_ls_number_reflns         6236
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0191P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.070
_refine_diff_density_min         -1.898
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2884(3) 0.07002(13) 0.7011(3) 0.0211(4) Uani d . . . 1 . .
H H1A 0.284009 0.048959 0.582765 0.032000 Uiso calc U . R 1 . .
H H1B 0.175905 0.048905 0.761688 0.032000 Uiso calc U . R 1 . .
H H1C 0.405017 0.048788 0.758754 0.032000 Uiso calc U . R 1 . .
C C2 0.5075(3) 0.21072(12) 0.6098(2) 0.0123(3) Uani d . . . 1 . .
C C3 0.6434(3) 0.15187(13) 0.5545(3) 0.0164(4) Uani d . . . 1 . .
H H3 0.619851 0.091471 0.562320 0.020000 Uiso calc U . R 1 . .
C C4 0.8136(3) 0.18194(14) 0.4878(3) 0.0199(4) Uani d . . . 1 . .
H H4 0.906111 0.141841 0.448586 0.024000 Uiso calc U . R 1 . .
C C5 0.8502(3) 0.27017(14) 0.4777(3) 0.0203(4) Uani d . . . 1 . .
H H5 0.967670 0.290896 0.433961 0.024000 Uiso calc U . R 1 . .
C C6 0.7123(3) 0.32672(14) 0.5325(3) 0.0198(4) Uani d . . . 1 . .
H H6 0.733091 0.387370 0.526051 0.024000 Uiso calc U . R 1 . .
I I1 0.20628(2) 0.44286(2) 0.69827(2) 0.01544(4) Uani d . . . 1 . .
N N1 0.5479(2) 0.29589(10) 0.5951(2) 0.0154(3) Uani d . . . 1 . .
H H1 0.461433 0.333372 0.628606 0.018000 Uiso calc U . R 1 . .
S S1 0.28867(7) 0.18656(3) 0.70141(7) 0.01786(10) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 S1 . 1.801(2) ?
C2 N1 . 1.352(2) ?
C2 C3 . 1.389(3) ?
C2 S1 . 1.7394(19) ?
C3 C4 . 1.387(3) ?
C4 C5 . 1.390(3) ?
C5 C6 . 1.375(3) ?
C6 N1 . 1.343(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C2 C3 . . 117.81(17) ?
N1 C2 S1 . . 115.49(14) ?
C3 C2 S1 . . 126.69(15) ?
C4 C3 C2 . . 119.50(18) ?
C3 C4 C5 . . 120.66(18) ?
C6 C5 C4 . . 118.40(19) ?
N1 C6 C5 . . 119.73(19) ?
C6 N1 C2 . . 123.90(17) ?
C2 S1 C1 . . 102.43(9) ?

