# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_mo_CM_2_25_A_2_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2114646'
loop_
_audit_author_name
_audit_author_address
'Michael Young'
;University of Toledo
United States of America
;
_audit_update_record             
;
2021-10-07 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8 I N O4'
_chemical_formula_weight         321.06

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.4419(15)
_cell_length_b                   9.9961(10)
_cell_length_c                   7.1719(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.5080(10)
_cell_angle_gamma                90
_cell_volume                     1104.97(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      1.32
_cell_measurement_theta_max      33.14

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   0.74374
_exptl_transmission_factor_max   0.907
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    2.892
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADBS; Bruker; 2017)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXIII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19196
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.321
_diffrn_reflns_theta_max         33.141
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4011
_reflns_number_gt                3707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4011
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0191
_refine_ls_R_factor_gt           0.0168
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   0.699
_refine_ls_restrained_S_all      0.699
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.36186(2) 1.05067(2) 0.58333(2) 0.02046(6) Uani 1 1 d . . . . .
O1 O 0.39212(9) 0.35566(11) 0.57965(17) 0.0309(2) Uani 1 1 d . . . . .
N1 N 0.32526(9) 0.42230(14) 0.58764(18) 0.0237(2) Uani 1 1 d . . . . .
C1 C 0.25901(8) 0.64706(13) 0.53822(17) 0.0181(2) Uani 1 1 d . . . . .
O2 O 0.25370(8) 0.37438(13) 0.60985(18) 0.0364(3) Uani 1 1 d . . . . .
C2 C 0.33252(10) 0.56849(13) 0.57528(19) 0.0177(2) Uani 1 1 d . . . . .
C3 C 0.41401(8) 0.62384(14) 0.61280(18) 0.0195(2) Uani 1 1 d . . . . .
H3 H 0.461963 0.568724 0.636274 0.023 Uiso 1 1 calc R U . . .
O3 O 0.11155(9) 0.61610(18) 0.6006(2) 0.0567(5) Uani 1 1 d . . . . .
C4 C 0.42374(8) 0.76151(14) 0.61521(18) 0.0192(2) Uani 1 1 d . . . . .
H4 H 0.478016 0.799922 0.640829 0.023 Uiso 1 1 calc R U . . .
O4 O 0.16093(7) 0.52813(12) 0.33829(17) 0.0261(2) Uani 1 1 d . . . . .
C5 C 0.35054(9) 0.84179(16) 0.57845(16) 0.0177(2) Uani 1 1 d . . . . .
C6 C 0.26917(8) 0.78560(14) 0.53953(18) 0.0192(2) Uani 1 1 d . . . . .
H6 H 0.221315 0.840603 0.514266 0.023 Uiso 1 1 calc R U . . .
C7 C 0.16888(9) 0.59423(16) 0.4988(2) 0.0263(3) Uani 1 1 d . . . . .
C8 C 0.07661(11) 0.4660(2) 0.2933(3) 0.0360(4) Uani 1 1 d . . . . .
H8A H 0.032471 0.534146 0.270779 0.043 Uiso 1 1 calc R U . . .
H8AB H 0.060288 0.410199 0.396060 0.043 Uiso 1 1 calc R U . . .
C9 C 0.08490(13) 0.3832(3) 0.1217(3) 0.0527(6) Uani 1 1 d . . . . .
H9A H 0.101191 0.439483 0.021156 0.079 Uiso 1 1 calc R U . . .
H9B H 0.030326 0.341070 0.087787 0.079 Uiso 1 1 calc R U . . .
H9C H 0.128495 0.315919 0.145899 0.079 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
I1 C5 2.0954(17) . ?
O1 N1 1.233(2) . ?
N1 O2 1.2237(17) . ?
N1 C2 1.4688(18) . ?
C1 C2 1.392(2) . ?
C1 C6 1.3937(17) . ?
C1 C7 1.4994(18) . ?
C2 C3 1.3859(19) . ?
C3 C4 1.3843(18) . ?
C3 H3 0.9300 . ?
O3 C7 1.2015(18) . ?
C4 C5 1.398(2) . ?
C4 H4 0.9300 . ?
O4 C7 1.3265(19) . ?
O4 C8 1.4607(19) . ?
C5 C6 1.3889(18) . ?
C6 H6 0.9300 . ?
C8 C9 1.495(3) . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O1 124.06(15) . . ?
O2 N1 C2 118.05(14) . . ?
O1 N1 C2 117.87(14) . . ?
C2 C1 C6 117.97(12) . . ?
C2 C1 C7 125.02(12) . . ?
C6 C1 C7 117.00(12) . . ?
C3 C2 C1 122.13(13) . . ?
C3 C2 N1 117.21(14) . . ?
C1 C2 N1 120.56(13) . . ?
C4 C3 C2 119.72(13) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.84(12) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C7 O4 C8 115.93(13) . . ?
C6 C5 C4 121.12(14) . . ?
C6 C5 I1 118.67(11) . . ?
C4 C5 I1 120.21(10) . . ?
C5 C6 C1 120.21(13) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O3 C7 O4 125.85(14) . . ?
O3 C7 C1 122.10(14) . . ?
O4 C7 C1 111.99(11) . . ?
O4 C8 C9 107.28(16) . . ?
O4 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O4 C8 H8AB 110.3 . . ?
C9 C8 H8AB 110.3 . . ?
H8A C8 H8AB 108.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         0.793
_refine_diff_density_min         -0.820
_refine_diff_density_rms         0.072


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/Hexanes'
####################################################################### 
# 
# 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_mo_VL_1_136_N_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2114648'
loop_
_audit_author_name
_audit_author_address
'Michael Young'
;University of Toledo
United States of America
;
_audit_update_record             
;
2021-10-07 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 Cl F2 N O'
_chemical_formula_weight         223.65

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.823
_cell_length_b                   6.388
_cell_length_c                   17.532
_cell_angle_alpha                96.89
_cell_angle_beta                 93.82
_cell_angle_gamma                91.98
_cell_volume                     534.6
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6653
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.54

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   0.882375
_exptl_transmission_factor_max   0.975
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    0.353
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADBS; Bruker; 2017)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXIII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8945
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_av_R_equivalents  0.0117
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         30.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3247
_reflns_number_gt                3039
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3247
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.74337(15) 0.61896(10) 0.97118(4) 0.02540(17) Uani 1 1 d . . . . .
H11B H 0.854(4) 0.674(3) 0.9510(9) 0.044(4) Uiso 1 1 d . . . . .
H11A H 0.602(3) 0.684(2) 0.9577(8) 0.030(3) Uiso 1 1 d . . . . .
F1 F -0.25174(15) 0.21846(12) 0.50584(4) 0.0433(2) Uani 1 1 d . . . . .
N1 N 0.74291(15) 0.19788(12) 0.90602(4) 0.01918(16) Uani 1 1 d . . . . .
H10C H 0.722(3) 0.316(2) 0.9342(8) 0.028(3) Uiso 1 1 d . . . . .
H10B H 0.887(3) 0.136(2) 0.9290(8) 0.032(3) Uiso 1 1 d . . . . .
C1 C 0.7988(2) 0.23192(18) 0.82562(5) 0.0290(2) Uani 1 1 d . . . . .
H1A H 0.824660 0.093890 0.795265 0.035 Uiso 1 1 calc R U . . .
H1AB H 0.973546 0.318480 0.826533 0.035 Uiso 1 1 calc R U . . .
H10A H 0.575(3) 0.119(2) 0.9073(8) 0.035(3) Uiso 1 1 d . . . . .
F2 F -0.16931(17) 0.83605(10) 0.67965(4) 0.0433(2) Uani 1 1 d . . . . .
Cl2 Cl 1.23330(4) 0.85793(3) 0.90217(2) 0.02219(10) Uani 1 1 d . . . . .
C2 C 0.56748(19) 0.33981(15) 0.78723(5) 0.02432(19) Uani 1 1 d . . . . .
H2 H 0.514361 0.472419 0.811092 0.029 Uiso 1 1 calc R U . . .
C3 C 0.43296(18) 0.25797(15) 0.72110(5) 0.0241(2) Uani 1 1 d . . . . .
H3 H 0.483695 0.121866 0.699976 0.029 Uiso 1 1 calc R U . . .
C4 C 0.21302(18) 0.35741(14) 0.67732(5) 0.02006(17) Uani 1 1 d . . . . .
C5 C 0.0847(2) 0.24233(15) 0.61058(5) 0.02459(19) Uani 1 1 d . . . . .
H5 H 0.141034 0.104520 0.593521 0.030 Uiso 1 1 calc R U . . .
C8 C -0.0827(2) 0.64042(15) 0.65689(5) 0.02519(19) Uani 1 1 d . . . . .
C9 C 0.12735(19) 0.56150(14) 0.70071(5) 0.02287(18) Uani 1 1 d . . . . .
H9 H 0.212104 0.643055 0.745626 0.027 Uiso 1 1 calc R U . . .
C7 C -0.2160(2) 0.53209(16) 0.59086(5) 0.0269(2) Uani 1 1 d . . . . .
H7 H -0.360356 0.591305 0.561910 0.032 Uiso 1 1 calc R U . . .
C6 C -0.1257(2) 0.33261(17) 0.56985(5) 0.0268(2) Uani 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
O1 H11B 0.758(19) . ?
O1 H11A 0.846(15) . ?
F1 C6 1.3576(10) . ?
N1 C1 1.4923(11) . ?
N1 H10C 0.863(13) . ?
N1 H10B 0.906(15) . ?
N1 H10A 0.941(16) . ?
C1 C2 1.4958(12) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
F2 C8 1.3543(11) . ?
C2 C3 1.3302(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.4741(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.3994(12) . ?
C4 C9 1.4037(12) . ?
C5 C6 1.3837(13) . ?
C5 H5 0.9500 . ?
C8 C9 1.3765(13) . ?
C8 C7 1.3823(13) . ?
C9 H9 0.9500 . ?
C7 C6 1.3771(14) . ?
C7 H7 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H11B O1 H11A 100.4(16) . . ?
C1 N1 H10C 111.4(9) . . ?
C1 N1 H10B 111.1(9) . . ?
H10C N1 H10B 106.3(13) . . ?
C1 N1 H10A 111.4(9) . . ?
H10C N1 H10A 105.1(12) . . ?
H10B N1 H10A 111.4(13) . . ?
N1 C1 C2 112.13(7) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1AB 109.2 . . ?
C2 C1 H1AB 109.2 . . ?
H1A C1 H1AB 107.9 . . ?
C3 C2 C1 122.80(9) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 C3 C4 126.50(8) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C5 C4 C9 119.30(8) . . ?
C5 C4 C3 118.42(8) . . ?
C9 C4 C3 122.28(8) . . ?
C6 C5 C4 118.89(8) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
F2 C8 C9 118.67(8) . . ?
F2 C8 C7 116.95(8) . . ?
C9 C8 C7 124.38(9) . . ?
C8 C9 C4 118.27(8) . . ?
C8 C9 H9 120.9 . . ?
C4 C9 H9 120.9 . . ?
C6 C7 C8 115.53(8) . . ?
C6 C7 H7 122.2 . . ?
C8 C7 H7 122.2 . . ?
F1 C6 C7 117.94(9) . . ?
F1 C6 C5 118.44(9) . . ?
C7 C6 C5 123.62(9) . . ?

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/Water'
####################################################################### 
# 
# 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_mo_CM_2_25_B2_0ma_d
_database_code_depnum_ccdc_archive 'CCDC 2114647'
loop_
_audit_author_name
_audit_author_address
'Michael Young'
;University of Toledo
United States of America
;
_audit_update_record             
;
2021-10-07 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8 I N O4'
_chemical_formula_weight         321.06

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   8.0269(8)
_cell_length_b                   18.6742(18)
_cell_length_c                   7.0465(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1056.24(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      30.11

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   0.714012
_exptl_transmission_factor_max   0.897
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    3.025
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADBS; Bruker; 2017)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXIII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15794
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.181
_diffrn_reflns_theta_max         30.111
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3093
_reflns_number_gt                2936
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.41(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3093
_refine_ls_number_parameters     137
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   0.847
_refine_ls_restrained_S_all      0.846
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.58717(2) 0.28933(2) 0.5035(3) 0.02238(13) Uani 1 1 d . . . . .
O1 O 0.2084(7) 0.3739(3) 0.6587(7) 0.0326(13) Uani 1 1 d . . . . .
N1 N 0.2653(3) 0.39199(14) 0.506(2) 0.0180(5) Uani 1 1 d . . . . .
C1 C 0.4062(3) 0.51115(19) 0.510(2) 0.0136(7) Uani 1 1 d . . . . .
C2 C 0.4178(3) 0.43641(17) 0.506(2) 0.0146(6) Uani 1 1 d . . . . .
O2 O 0.2105(7) 0.3728(3) 0.3508(6) 0.0279(11) Uani 1 1 d . . . . .
O3 O 0.1097(3) 0.51651(17) 0.511(2) 0.0360(9) Uani 1 1 d . . . . .
C3 C 0.5700(4) 0.40057(18) 0.501(2) 0.0154(5) Uani 1 1 d . . . . .
C4 C 0.7171(3) 0.44121(16) 0.5044(19) 0.0182(5) Uani 1 1 d . . . . .
H4 H 0.820102 0.418410 0.506684 0.022 Uiso 1 1 calc R U . . .
O4 O 0.2562(2) 0.61892(12) 0.5070(15) 0.0201(5) Uani 1 1 d . . . . .
C5 C 0.7087(3) 0.51541(17) 0.5044(17) 0.0198(6) Uani 1 1 d . . . . .
H5 H 0.806476 0.542069 0.500485 0.024 Uiso 1 1 calc R U . . .
C6 C 0.5556(4) 0.55051(17) 0.5102(16) 0.0160(7) Uani 1 1 d . . . . .
H6 H 0.552167 0.600261 0.514424 0.019 Uiso 1 1 calc R U . . .
C7 C 0.2416(3) 0.54807(17) 0.5049(19) 0.0183(6) Uani 1 1 d . . . . .
C8 C 0.1004(3) 0.6591(2) 0.500(3) 0.0251(8) Uani 1 1 d . . . . .
H8A H 0.030491 0.646486 0.607288 0.030 Uiso 1 1 calc R U . . .
H8AB H 0.040393 0.648135 0.384249 0.030 Uiso 1 1 calc R U . . .
C9 C 0.1426(4) 0.73737(16) 0.5066(15) 0.0235(6) Uani 1 1 d . . . . .
H9A H 0.216896 0.748771 0.404205 0.035 Uiso 1 1 calc R U . . .
H9B H 0.195499 0.748291 0.625338 0.035 Uiso 1 1 calc R U . . .
H9C H 0.042479 0.765101 0.494467 0.035 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
I1 C3 2.082(3) . ?
O1 N1 1.220(14) . ?
N1 O2 1.229(14) . ?
N1 C2 1.479(3) . ?
C1 C2 1.399(4) . ?
C1 C6 1.406(4) . ?
C1 C7 1.491(4) . ?
C2 C3 1.393(4) . ?
O3 C7 1.212(4) . ?
C3 C4 1.404(4) . ?
C4 C5 1.387(4) . ?
C4 H4 0.9300 . ?
O4 C7 1.328(4) . ?
O4 C8 1.460(3) . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.500(5) . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 124.8(3) . . ?
O1 N1 C2 117.6(11) . . ?
O2 N1 C2 117.5(10) . . ?
C2 C1 C6 117.7(2) . . ?
C2 C1 C7 121.3(2) . . ?
C6 C1 C7 120.9(3) . . ?
C3 C2 C1 122.6(2) . . ?
C3 C2 N1 117.2(3) . . ?
C1 C2 N1 120.3(2) . . ?
C2 C3 C4 118.5(3) . . ?
C2 C3 I1 122.5(2) . . ?
C4 C3 I1 118.9(2) . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C7 O4 C8 115.9(2) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O3 C7 O4 124.1(3) . . ?
O3 C7 C1 123.3(3) . . ?
O4 C7 C1 112.5(2) . . ?
O4 C8 C9 107.9(3) . . ?
O4 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
O4 C8 H8AB 110.1 . . ?
C9 C8 H8AB 110.1 . . ?
H8A C8 H8AB 108.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         1.638
_refine_diff_density_min         -1.336
_refine_diff_density_rms         0.122


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/Hexanes'
