# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_T1
_database_code_depnum_ccdc_archive 'CCDC 2168128'
loop_
_audit_author_name
_audit_author_address
'Miriam Calabrese'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '4-cyanopyridinium periodate'
_chemical_formula_moiety         'I O4, C6 H5 N2'
_chemical_formula_sum            'C6 H5 I N2 O4'
_chemical_formula_weight         296.02
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4965(7)
_cell_length_b                   20.5064(18)
_cell_length_c                   10.5561(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.900(3)
_cell_angle_gamma                90
_cell_volume                     1817.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9627
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.67
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.510
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22823
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.609
_diffrn_reflns_theta_min         2.426
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4396
_reflns_number_total             6446
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3(Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         6446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0243P)²+0.5144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0650
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C5(H5), C1(H1), C4(H4), C2(H2), N3(H3), C7(H7), C10(H10), C11(H11),
 C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.36775(2) 0.43451(2) 0.59973(2) 0.04290(6) Uani 1 1 d . . . . .
I2 I 0.12585(2) 0.60492(2) 0.82501(2) 0.04910(6) Uani 1 1 d . . . . .
N1 N 0.4030(3) 0.40512(12) 0.1957(3) 0.0505(6) Uani 1 1 d . . . . .
H1A H 0.444348 0.431812 0.254414 0.061 Uiso 1 1 calc R U . . .
N2 N 0.1067(4) 0.24681(18) -0.1518(3) 0.0891(11) Uani 1 1 d . . . . .
C5 C 0.3577(4) 0.42780(15) 0.0783(3) 0.0580(8) Uani 1 1 d . . . . .
H5 H 0.374068 0.471433 0.060199 0.070 Uiso 1 1 calc R U . . .
C1 C 0.3874(3) 0.34311(15) 0.2267(3) 0.0530(7) Uani 1 1 d . . . . .
H1 H 0.423011 0.328912 0.309891 0.064 Uiso 1 1 calc R U . . .
C6 C 0.1796(4) 0.27986(17) -0.0802(3) 0.0631(8) Uani 1 1 d . . . . .
C4 C 0.2876(4) 0.38759(15) -0.0152(3) 0.0560(7) Uani 1 1 d . . . . .
H4 H 0.254974 0.403036 -0.097944 0.067 Uiso 1 1 calc R U . . .
C3 C 0.2655(3) 0.32331(13) 0.0148(3) 0.0458(6) Uani 1 1 d . . . . .
C2 C 0.3188(3) 0.30029(13) 0.1360(3) 0.0489(6) Uani 1 1 d . . . . .
H2 H 0.308318 0.256456 0.155725 0.059 Uiso 1 1 calc R U . . .
N3 N 0.0868(3) 0.60999(12) 0.4385(3) 0.0564(6) Uani 1 1 d . . . . .
H3 H 0.038566 0.593185 0.496488 0.068 Uiso 1 1 calc R U . . .
N4 N 0.4111(3) 0.71232(16) 0.1027(3) 0.0748(8) Uani 1 1 d . . . . .
C12 C 0.3353(4) 0.68941(15) 0.1699(3) 0.0544(7) Uani 1 1 d . . . . .
C9 C 0.2435(3) 0.66146(13) 0.2611(3) 0.0431(6) Uani 1 1 d . . . . .
C7 C 0.1493(4) 0.66841(15) 0.4583(3) 0.0601(8) Uani 1 1 d . . . . .
H7 H 0.138449 0.691156 0.532658 0.072 Uiso 1 1 calc R U . . .
C10 C 0.1737(4) 0.60071(14) 0.2413(3) 0.0537(7) Uani 1 1 d . . . . .
H10 H 0.180473 0.577258 0.166893 0.064 Uiso 1 1 calc R U . . .
C11 C 0.0947(4) 0.57602(15) 0.3337(3) 0.0596(8) Uani 1 1 d . . . . .
H11 H 0.046401 0.535273 0.322778 0.072 Uiso 1 1 calc R U . . .
O2 O 0.3011(3) 0.35893(11) 0.6477(3) 0.0879(8) Uani 1 1 d . . . . .
O3 O 0.4895(3) 0.46878(10) 0.7322(2) 0.0628(6) Uani 1 1 d . . . . .
O1 O 0.4815(3) 0.42346(13) 0.4764(2) 0.0776(7) Uani 1 1 d . . . . .
O4 O 0.2003(2) 0.48321(11) 0.5516(2) 0.0702(6) Uani 1 1 d . . . . .
O8 O 0.0580(3) 0.65376(14) 0.9405(2) 0.0832(8) Uani 1 1 d . . . . .
O6 O 0.2640(3) 0.65005(14) 0.7542(2) 0.0817(7) Uani 1 1 d . . . . .
O7 O -0.0294(3) 0.58319(13) 0.7005(3) 0.0904(8) Uani 1 1 d . . . . .
O5 O 0.2180(4) 0.53604(16) 0.8989(4) 0.1349(14) Uani 1 1 d . . . . .
C8 C 0.2300(4) 0.69555(14) 0.3697(3) 0.0552(7) Uani 1 1 d . . . . .
H8 H 0.275331 0.736747 0.383146 0.066 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 O2 1.752(2) . ?
I1 O3 1.753(2) . ?
I1 O1 1.752(2) . ?
I1 O4 1.748(2) . ?
I2 O8 1.743(2) . ?
I2 O6 1.751(2) . ?
I2 O7 1.769(3) . ?
I2 O5 1.740(3) . ?
N1 C5 1.324(4) . ?
N1 C1 1.325(4) . ?
N2 C6 1.127(4) . ?
C5 C4 1.352(4) . ?
C1 C2 1.362(4) . ?
C6 C3 1.451(4) . ?
C4 C3 1.375(4) . ?
C3 C2 1.373(4) . ?
N3 C7 1.314(4) . ?
N3 C11 1.317(4) . ?
N4 C12 1.132(4) . ?
C12 C9 1.448(4) . ?
C9 C10 1.381(4) . ?
C9 C8 1.363(4) . ?
C7 C8 1.361(4) . ?
C10 C11 1.365(4) . ?

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 I1 O3 107.53(12) . . ?
O2 I1 O1 109.91(13) . . ?
O1 I1 O3 108.63(12) . . ?
O4 I1 O2 107.72(12) . . ?
O4 I1 O3 110.86(11) . . ?
O4 I1 O1 112.07(12) . . ?
O8 I2 O6 108.13(14) . . ?
O8 I2 O7 112.03(13) . . ?
O6 I2 O7 106.73(14) . . ?
O5 I2 O8 109.12(16) . . ?
O5 I2 O6 109.60(15) . . ?
O5 I2 O7 111.14(17) . . ?
C5 N1 C1 122.9(3) . . ?
N1 C5 C4 120.1(3) . . ?
N1 C1 C2 119.6(3) . . ?
N2 C6 C3 176.9(4) . . ?
C5 C4 C3 118.5(3) . . ?
C4 C3 C6 120.1(3) . . ?
C2 C3 C6 119.4(3) . . ?
C2 C3 C4 120.5(3) . . ?
C1 C2 C3 118.5(3) . . ?
C7 N3 C11 123.0(3) . . ?
N4 C12 C9 177.2(4) . . ?
C10 C9 C12 121.3(3) . . ?
C8 C9 C12 118.7(3) . . ?
C8 C9 C10 120.0(3) . . ?
N3 C7 C8 119.8(3) . . ?
C11 C10 C9 118.2(3) . . ?
N3 C11 C10 119.9(3) . . ?
C7 C8 C9 119.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_T1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2168130'
loop_
_audit_author_name
_audit_author_address
'Miriam Calabrese'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '3-carboxypyridinium periodate'
_chemical_formula_moiety         'I O4, C6 H6 N O2'
_chemical_formula_sum            'C6 H6 I N O6'
_chemical_formula_weight         315.02
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.5924(2)
_cell_length_b                   16.7630(6)
_cell_length_c                   10.0824(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.879(2)
_cell_angle_gamma                90
_cell_volume                     921.40(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9627
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.67
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.481
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   0.7468
_exptl_transmission_factor_min   0.4569
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13469
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.721
_diffrn_reflns_theta_min         2.430
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2624
_reflns_number_total             3476
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3(Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      0.867
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1153
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.47324(3) 0.37501(2) 0.06835(2) 0.03754(9) Uani 1 1 d . . . . .
O2 O 0.3550(5) 0.29066(12) 0.1381(2) 0.0564(6) Uani 1 1 d . . . . .
O3 O 0.2674(5) 0.45543(15) 0.0471(3) 0.0611(6) Uani 1 1 d . . . . .
O1 O 0.5281(6) 0.3459(2) -0.0892(3) 0.0739(9) Uani 1 1 d . . . . .
O4 O 0.7544(5) 0.39982(18) 0.1784(4) 0.0669(7) Uani 1 1 d . . . . .
C4 C 0.1049(6) 0.37900(13) 0.5363(3) 0.0376(5) Uani 1 1 d . . . . .
C6 C 0.2241(6) 0.36692(16) 0.4189(3) 0.0417(6) Uani 1 1 d . . . . .
N1 N 0.0744(5) 0.45644(16) 0.7253(3) 0.0456(5) Uani 1 1 d . . . . .
C5 C 0.1790(6) 0.44299(17) 0.6208(3) 0.0416(5) Uani 1 1 d . . . . .
C3 C -0.0786(6) 0.33016(18) 0.5607(3) 0.0459(6) Uani 1 1 d . . . . .
C1 C -0.1024(6) 0.4100(2) 0.7524(3) 0.0486(7) Uani 1 1 d . . . . .
H8 H -0.170717 0.421377 0.826291 0.058 Uiso 1 1 calc R U . . .
C2 C -0.1840(7) 0.3450(2) 0.6705(4) 0.0529(7) Uani 1 1 d . . . . .
O5 O 0.1604(5) 0.29988(13) 0.3555(2) 0.0530(6) Uani 1 1 d . . . . .
O6 O 0.3622(6) 0.41549(17) 0.3888(3) 0.0673(7) Uani 1 1 d . . . . .
H3 H 0.313(7) 0.483(2) 0.615(4) 0.055(10) Uiso 1 1 d . . . . .
H7 H 0.237(7) 0.285(2) 0.276(4) 0.067(11) Uiso 1 1 d . . . . .
H4 H -0.117(8) 0.276(3) 0.507(5) 0.075(12) Uiso 1 1 d . . . . .
H5 H -0.297(8) 0.303(3) 0.688(4) 0.067(12) Uiso 1 1 d . . . . .
H2 H 0.127(6) 0.494(2) 0.778(3) 0.040(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O2 1.7714(19) . ?
I1 O3 1.754(2) . ?
I1 O1 1.753(2) . ?
I1 O4 1.760(3) . ?
C4 C6 1.496(4) . ?
C4 C5 1.375(4) . ?
C4 C3 1.377(4) . ?
C6 O5 1.303(4) . ?
C6 O6 1.207(4) . ?
N1 C5 1.333(4) . ?
N1 C1 1.334(4) . ?
C3 C2 1.388(4) . ?
C1 C2 1.381(5) . ?

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
O3 I1 O2 111.66(13) . . ?
O3 I1 O4 111.40(14) . . ?
O1 I1 O2 107.07(12) . . ?
O1 I1 O3 110.23(15) . . ?
O1 I1 O4 108.96(15) . . ?
O4 I1 O2 107.36(14) . . ?
C5 C4 C6 118.0(3) . . ?
C5 C4 C3 119.1(3) . . ?
C3 C4 C6 122.8(3) . . ?
O5 C6 C4 112.6(3) . . ?
O6 C6 C4 122.0(3) . . ?
O6 C6 O5 125.4(3) . . ?
C5 N1 C1 122.6(3) . . ?
N1 C5 C4 119.8(3) . . ?
C4 C3 C2 120.1(3) . . ?
N1 C1 C2 119.9(3) . . ?
C1 C2 C3 118.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_T1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2168129'
loop_
_audit_author_name
_audit_author_address
'Miriam Calabrese'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_audit_creation_date             2022-04-22
# end Validation Reply Form
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '3-nitropyridinium periodate'
_chemical_formula_moiety         'I O4, C5 H5 N2 O2'
_chemical_formula_sum            'C5 H5 I N2 O6'
_chemical_formula_weight         316.01
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.6795(4)
_cell_length_b                   19.8304(14)
_cell_length_c                   8.0659(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.643(2)
_cell_angle_gamma                90
_cell_volume                     895.60(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9627
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.67
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.584
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_special_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   0.7459
_exptl_transmission_factor_min   0.6088
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9764
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.617
_diffrn_reflns_theta_min         3.284
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2293
_reflns_number_total             2519
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3(Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0208
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0175P)²+0.5343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0467
_refine_ls_wR_factor_ref         0.0479
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.57174(2) 0.41818(2) 0.82813(2) 0.03339(5) Uani 1 1 d . . . . .
N1 N 0.1403(4) 0.39443(11) 0.2258(3) 0.0390(4) Uani 1 1 d . . . . .
H2 H 0.180(7) 0.4122(17) 0.138(5) 0.071(11) Uiso 1 1 d . . . . .
C3 C 0.1888(4) 0.31207(11) 0.4326(3) 0.0307(4) Uani 1 1 d . . . . .
C2 C 0.2566(4) 0.33977(12) 0.2923(3) 0.0356(5) Uani 1 1 d . . . . .
C5 C -0.1073(5) 0.39632(15) 0.4293(3) 0.0428(5) Uani 1 1 d . . . . .
C4 C 0.0043(4) 0.33976(13) 0.5032(3) 0.0385(5) Uani 1 1 d . . . . .
N2 N 0.3168(3) 0.25245(10) 0.5068(3) 0.0386(4) Uani 1 1 d . . . . .
O5 O 0.4479(4) 0.42108(11) 1.0137(3) 0.0638(6) Uani 1 1 d . . . . .
O4 O 0.4176(4) 0.46984(13) 0.6700(3) 0.0743(7) Uani 1 1 d . . . . .
O2 O 0.2326(3) 0.22152(10) 0.6138(2) 0.0518(5) Uani 1 1 d . . . . .
O1 O 0.5021(3) 0.23740(10) 0.4580(3) 0.0550(5) Uani 1 1 d . . . . .
O3 O 0.5665(4) 0.33552(11) 0.7497(3) 0.0642(6) Uani 1 1 d . . . . .
O6 O 0.8702(4) 0.44429(13) 0.8789(3) 0.0629(6) Uani 1 1 d . . . . .
C6 C -0.0362(5) 0.42362(13) 0.2893(3) 0.0397(5) Uani 1 1 d . . . . .
H5 H -0.040(5) 0.3198(15) 0.591(4) 0.049(8) Uiso 1 1 d . . . . .
H1 H 0.372(5) 0.3223(16) 0.234(4) 0.059(9) Uiso 1 1 d . . . . .
H4 H -0.227(6) 0.4173(15) 0.472(4) 0.060(10) Uiso 1 1 d . . . . .
H3 H -0.097(6) 0.4600(19) 0.245(4) 0.068(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O5 1.7580(19) . ?
I1 O4 1.751(2) . ?
I1 O3 1.756(2) . ?
I1 O6 1.754(2) . ?
N1 C2 1.334(3) . ?
N1 C6 1.332(3) . ?
C3 C2 1.370(3) . ?
C3 C4 1.387(3) . ?
C3 N2 1.463(3) . ?
C5 C4 1.374(4) . ?
C5 C6 1.373(4) . ?
N2 O2 1.220(3) . ?
N2 O1 1.221(3) . ?

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
O4 I1 O5 112.23(11) . . ?
O4 I1 O3 107.91(11) . . ?
O4 I1 O6 110.05(12) . . ?
O3 I1 O5 110.62(11) . . ?
O6 I1 O5 107.49(11) . . ?
O6 I1 O3 108.49(12) . . ?
C6 N1 C2 123.5(2) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 N2 118.2(2) . . ?
C4 C3 N2 120.7(2) . . ?
N1 C2 C3 118.0(2) . . ?
C6 C5 C4 120.1(2) . . ?
C5 C4 C3 118.0(2) . . ?
O2 N2 C3 118.0(2) . . ?
O2 N2 O1 124.5(2) . . ?
O1 N2 C3 117.5(2) . . ?
N1 C6 C5 119.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT430_T1                  
;
PROBLEM: Short Inter D...A Contact  O3       ..N2       .       2.76 Ang.  
RESPONSE: strong pi-hole interaction
;
####################################################################### 
# 
# 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_T1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2168131'
loop_
_audit_author_name
_audit_author_address
'Miriam Calabrese'
;Politecnico di Milano
Italy
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_audit_creation_date             2022-04-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '3-fluoropyridinium periodate'
_chemical_formula_moiety         'I O4, C5 H5 F N'
_chemical_formula_sum            'C5 H5 F I N O4'
_chemical_formula_weight         289.00
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.5213(8)
_cell_length_b                   36.592(5)
_cell_length_c                   8.1602(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.381(6)
_cell_angle_gamma                90
_cell_volume                     1581.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9627
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.67
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.042
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17574
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.721
_diffrn_reflns_theta_min         1.113
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4056
_reflns_number_total             4485
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3(Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.825
_refine_diff_density_min         -1.305
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0162P)²+4.3200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0723
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C4(H1), C10(H2), C6(H3), C5(H4), C3(H5), C8(H6), C7(H7), C1(H8), N1(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.61021(5) 0.67912(2) 0.85664(3) 0.02943(7) Uani 1 1 d . . . . .
I2 I 0.57963(5) 0.57721(2) 0.25675(3) 0.03075(7) Uani 1 1 d . . . . .
C4 C 0.2525(7) 0.67930(10) 0.2766(5) 0.0282(8) Uani 1 1 d . . . . .
H1 H 0.352112 0.668127 0.216229 0.034 Uiso 1 1 calc R U . . .
C10 C 0.1778(9) 0.56900(12) 0.7075(5) 0.0379(9) Uani 1 1 d . . . . .
H2 H 0.292172 0.579698 0.657418 0.046 Uiso 1 1 calc R U . . .
C2 C -0.0326(9) 0.67480(13) 0.4341(6) 0.0400(10) Uani 1 1 d . . . . .
C6 C -0.1059(9) 0.57433(13) 0.8711(6) 0.0424(10) Uani 1 1 d . . . . .
H3 H -0.183144 0.589142 0.934238 0.051 Uiso 1 1 calc R U . . .
C9 C 0.1257(8) 0.53240(12) 0.6904(5) 0.0352(9) Uani 1 1 d . . . . .
C5 C 0.2565(9) 0.71544(13) 0.2873(6) 0.0402(10) Uani 1 1 d . . . . .
H4 H 0.358264 0.729013 0.236530 0.048 Uiso 1 1 calc R U . . .
C3 C 0.1141(9) 0.65814(13) 0.3473(6) 0.0407(10) Uani 1 1 d . . . . .
H5 H 0.117348 0.632832 0.337866 0.049 Uiso 1 1 calc R U . . .
C8 C -0.0433(8) 0.51622(12) 0.7632(6) 0.0379(9) Uani 1 1 d . . . . .
H6 H -0.076444 0.491285 0.751529 0.045 Uiso 1 1 calc R U . . .
C7 C -0.1620(8) 0.53811(12) 0.8539(6) 0.0390(10) Uani 1 1 d . . . . .
H7 H -0.279889 0.528188 0.903180 0.047 Uiso 1 1 calc R U . . .
C1 C -0.0429(9) 0.71193(13) 0.4492(6) 0.0415(10) Uani 1 1 d . . . . .
H8 H -0.146659 0.722882 0.507044 0.050 Uiso 1 1 calc R U . . .
O2 O 0.5152(8) 0.57681(13) 0.4549(5) 0.0664(11) Uani 1 1 d . . . . .
O3 O 0.4354(8) 0.54096(10) 0.1238(5) 0.0604(10) Uani 1 1 d . . . . .
O1 O 0.4680(8) 0.61840(10) 0.1505(5) 0.0620(11) Uani 1 1 d . . . . .
O4 O 0.9070(6) 0.57501(10) 0.2877(5) 0.0545(9) Uani 1 1 d . . . . .
O7 O 0.5931(8) 0.71518(10) 0.7114(5) 0.0571(10) Uani 1 1 d . . . . .
O6 O 0.3962(7) 0.64499(10) 0.7576(5) 0.0536(9) Uani 1 1 d . . . . .
O8 O 0.9180(7) 0.66129(12) 0.9144(5) 0.0645(11) Uani 1 1 d . . . . .
O5 O 0.5409(8) 0.69694(10) 1.0384(5) 0.0565(10) Uani 1 1 d . . . . .
F1 F -0.1742(6) 0.65359(9) 0.5045(4) 0.0638(9) Uani 1 1 d . . . . .
F2 F 0.2475(6) 0.51243(8) 0.6020(4) 0.0583(8) Uani 1 1 d . . . . .
N1 N 0.1090(9) 0.73269(14) 0.3740(6) 0.0600(12) Uani 1 1 d . . . . .
H9 H 0.110258 0.756128 0.381916 0.072 Uiso 1 1 calc R U . . .
N2 N 0.0598(8) 0.58866(11) 0.7977(5) 0.0376(8) Uani 1 1 d . . . . .
H10 H 0.097(10) 0.6103(15) 0.801(7) 0.046(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O7 1.758(3) . ?
I1 O6 1.752(3) . ?
I1 O8 1.756(3) . ?
I1 O5 1.759(3) . ?
I2 O2 1.751(3) . ?
I2 O3 1.756(3) . ?
I2 O1 1.761(3) . ?
I2 O4 1.755(3) . ?
C4 C5 1.325(6) . ?
C4 C3 1.329(6) . ?
C10 C9 1.368(6) . ?
C10 N2 1.324(6) . ?
C2 C3 1.361(6) . ?
C2 C1 1.367(7) . ?
C2 F1 1.341(5) . ?
C6 C7 1.359(6) . ?
C6 N2 1.335(6) . ?
C9 C8 1.374(6) . ?
C9 F2 1.334(5) . ?
C5 N1 1.374(6) . ?
C8 C7 1.376(6) . ?
C1 N1 1.395(7) . ?

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
O7 I1 O5 107.90(17) . . ?
O6 I1 O7 108.83(19) . . ?
O6 I1 O8 109.55(19) . . ?
O6 I1 O5 112.00(18) . . ?
O8 I1 O7 108.9(2) . . ?
O8 I1 O5 109.6(2) . . ?
O2 I2 O3 112.9(2) . . ?
O2 I2 O1 109.1(2) . . ?
O2 I2 O4 109.6(2) . . ?
O3 I2 O1 107.90(19) . . ?
O4 I2 O3 108.87(19) . . ?
O4 I2 O1 108.2(2) . . ?
C5 C4 C3 123.6(4) . . ?
N2 C10 C9 117.8(4) . . ?
C3 C2 C1 122.6(4) . . ?
F1 C2 C3 117.9(4) . . ?
F1 C2 C1 119.5(4) . . ?
N2 C6 C7 120.1(4) . . ?
C10 C9 C8 121.8(4) . . ?
F2 C9 C10 117.9(4) . . ?
F2 C9 C8 120.3(4) . . ?
C4 C5 N1 119.4(4) . . ?
C4 C3 C2 117.7(4) . . ?
C9 C8 C7 117.8(4) . . ?
C6 C7 C8 119.6(4) . . ?
C2 C1 N1 117.1(4) . . ?
C5 N1 C1 119.6(5) . . ?
C10 N2 C6 122.9(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
