# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_2(13-F4DIB)(14-DMeTetz)
_database_code_depnum_ccdc_archive 'CCDC 2040123'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
'bis(1,3-diiodo-2,4,5,6-tetrafluorobenzene) 1,4-dimethylhexahydro-s-tetrazine cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 0.5(C4 H12 N4)'
_chemical_formula_sum            'C8 H6 F4 I2 N2'
_chemical_formula_weight         459.95

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'
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'
N N 0.0061 0.0033 '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                   6.3151(9)
_cell_length_b                   8.5815(12)
_cell_length_c                   11.0306(15)
_cell_angle_alpha                103.485(5)
_cell_angle_beta                 96.047(6)
_cell_angle_gamma                93.183(5)
_cell_volume                     576.08(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9795
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.46

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.652
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    5.486
_shelx_estimated_absorpt_T_min   0.158
_shelx_estimated_absorpt_T_max   0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_T_max  0.63
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   .
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12764
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.449
_diffrn_reflns_theta_max         26.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2361
_reflns_number_gt                2288
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0112P)²+1.5122P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2361
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0213
_refine_ls_wR_factor_ref         0.0524
_refine_ls_wR_factor_gt          0.0519
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
I1 I 0.16848(3) 0.39776(2) 0.20376(2) 0.01983(7) Uani 1 1 d . . . . .
I2 I 0.36556(3) 0.86728(2) 0.70772(2) 0.01954(7) Uani 1 1 d . . . . .
F1 F 0.1428(3) 0.5982(2) 0.48054(19) 0.0250(4) Uani 1 1 d . . . . .
F2 F 0.7908(3) 0.9248(2) 0.57638(19) 0.0260(4) Uani 1 1 d . . . . .
F3 F 0.8991(3) 0.7896(3) 0.3465(2) 0.0264(4) Uani 1 1 d . . . . .
F4 F 0.6296(3) 0.5681(2) 0.18130(19) 0.0266(4) Uani 1 1 d . . . . .
C1 C 0.3791(5) 0.5764(4) 0.3280(3) 0.0190(6) Uani 1 1 d . . . . .
C2 C 0.3295(5) 0.6472(4) 0.4470(3) 0.0191(6) Uani 1 1 d . . . . .
C3 C 0.4624(5) 0.7646(4) 0.5333(3) 0.0175(6) Uani 1 1 d . . . . .
C4 C 0.6552(5) 0.8107(4) 0.4979(3) 0.0193(6) Uani 1 1 d . . . . .
C5 C 0.7119(5) 0.7421(4) 0.3803(3) 0.0196(6) Uani 1 1 d . . . . .
C6 C 0.5728(5) 0.6278(4) 0.2964(3) 0.0203(6) Uani 1 1 d . . . . .
N1 N -0.1024(4) 0.1435(3) 0.0135(2) 0.0178(5) Uani 1 1 d . . . . .
N2 N -0.1978(5) 0.0063(3) 0.0495(3) 0.0190(5) Uani 1 1 d . . . . .
C7 C -0.2735(6) 0.2350(4) -0.0266(3) 0.0231(7) Uani 1 1 d . . . . .
H7A H -0.211263 0.329275 -0.050185 0.035 Uiso 1 1 calc R U . . .
H7B H -0.359008 0.270129 0.042400 0.035 Uiso 1 1 calc R U . . .
H7C H -0.364864 0.166977 -0.099103 0.035 Uiso 1 1 calc R U . . .
C8 C -0.0310(5) -0.0880(4) 0.0879(3) 0.0191(6) Uani 1 1 d . . . . .
H8A H -0.096882 -0.182382 0.111460 0.023 Uiso 1 1 calc R U . . .
H8B H 0.060355 -0.022111 0.162719 0.023 Uiso 1 1 calc R U . . .
H1N2 H -0.270(7) -0.045(5) -0.012(4) 0.019(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 C1 2.099(3) . ?
I2 C3 2.090(3) . ?
F1 C2 1.347(4) . ?
F2 C4 1.341(4) . ?
F3 C5 1.347(4) . ?
F4 C6 1.348(4) . ?
C1 C6 1.383(5) . ?
C1 C2 1.388(5) . ?
C2 C3 1.384(4) . ?
C3 C4 1.382(5) . ?
C4 C5 1.387(5) . ?
C5 C6 1.378(5) . ?
N1 N2 1.448(4) . ?
N1 C7 1.461(4) . ?
N1 C8 1.477(4) 2 ?
N2 C8 1.451(4) . ?
N2 H1N2 0.80(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

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
C6 C1 C2 117.0(3) . . ?
C6 C1 I1 122.1(2) . . ?
C2 C1 I1 120.8(2) . . ?
F1 C2 C3 118.3(3) . . ?
F1 C2 C1 118.2(3) . . ?
C3 C2 C1 123.5(3) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 I2 122.8(2) . . ?
C2 C3 I2 119.9(2) . . ?
F2 C4 C3 120.5(3) . . ?
F2 C4 C5 118.4(3) . . ?
C3 C4 C5 121.1(3) . . ?
F3 C5 C6 119.9(3) . . ?
F3 C5 C4 120.4(3) . . ?
C6 C5 C4 119.6(3) . . ?
F4 C6 C5 118.0(3) . . ?
F4 C6 C1 120.5(3) . . ?
C5 C6 C1 121.4(3) . . ?
N2 N1 C7 108.5(3) . . ?
N2 N1 C8 109.7(2) . 2 ?
C7 N1 C8 111.3(3) . 2 ?
N1 N2 C8 109.5(3) . . ?
N1 N2 H1N2 105(3) . . ?
C8 N2 H1N2 110(3) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 N1 111.6(3) . 2 ?
N2 C8 H8A 109.3 . . ?
N1 C8 H8A 109.3 2 . ?
N2 C8 H8B 109.3 . . ?
N1 C8 H8B 109.3 2 . ?
H8A C8 H8B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 -179.4(3) . . . . ?
I1 C1 C2 F1 0.0(4) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
I1 C1 C2 C3 179.5(2) . . . . ?
F1 C2 C3 C4 178.7(3) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
F1 C2 C3 I2 -2.3(4) . . . . ?
C1 C2 C3 I2 178.1(2) . . . . ?
C2 C3 C4 F2 179.4(3) . . . . ?
I2 C3 C4 F2 0.4(4) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
I2 C3 C4 C5 -178.6(2) . . . . ?
F2 C4 C5 F3 0.1(5) . . . . ?
C3 C4 C5 F3 179.2(3) . . . . ?
F2 C4 C5 C6 -178.2(3) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
F3 C5 C6 F4 -0.7(5) . . . . ?
C4 C5 C6 F4 177.5(3) . . . . ?
F3 C5 C6 C1 -179.9(3) . . . . ?
C4 C5 C6 C1 -1.7(5) . . . . ?
C2 C1 C6 F4 -178.1(3) . . . . ?
I1 C1 C6 F4 2.6(4) . . . . ?
C2 C1 C6 C5 1.1(5) . . . . ?
I1 C1 C6 C5 -178.2(2) . . . . ?
C7 N1 N2 C8 179.1(3) . . . . ?
C8 N1 N2 C8 57.2(3) 2 . . . ?
N1 N2 C8 N1 -58.3(3) . . . 2 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7A I1 0.98 3.21 4.135(4) 158.0 2_565
C7 H7B I2 0.98 3.24 3.911(4) 126.9 2_566
C7 H7B F4 0.98 2.67 3.353(4) 127.4 1_455
C7 H7C I2 0.98 3.20 4.150(3) 163.4 1_444

_refine_diff_density_max         1.330
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.120

####################################################################### 
# 
# 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_2(13-F4DIB)(NMe4I)_UDMH
_database_code_depnum_ccdc_archive 'CCDC 2040126'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
'bis(1,3-diiodo-2,4,5,6-tetrafluorobenzene) tetramethylammonium iodide cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 F4 I2), C4 H12 N, I'
_chemical_formula_sum            'C16 H12 F8 I5 N'
_chemical_formula_weight         1004.77

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'
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'
N N 0.0061 0.0033 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.9907(5)
_cell_length_b                   21.4967(12)
_cell_length_c                   11.4868(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.673(2)
_cell_angle_gamma                90
_cell_volume                     2397.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9810
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.784
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.115
_exptl_absorpt_coefficient_mu    6.554
_shelx_estimated_absorpt_T_min   0.371
_shelx_estimated_absorpt_T_max   0.519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_T_max  0.52
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   .
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59566
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.056
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4901
_reflns_number_gt                4667
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0116P)²+5.0980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4901
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0182
_refine_ls_R_factor_gt           0.0168
_refine_ls_wR_factor_ref         0.0409
_refine_ls_wR_factor_gt          0.0399
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.003
_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 0.73163(2) 0.39957(2) 0.82633(2) 0.01998(5) Uani 1 1 d . . . . .
I2 I 0.83587(2) 0.65328(2) 1.05098(2) 0.01982(5) Uani 1 1 d . . . . .
F1 F 0.87724(17) 0.52084(8) 0.95171(19) 0.0290(4) Uani 1 1 d . . . . .
F2 F 0.50070(19) 0.65160(8) 0.95970(17) 0.0257(4) Uani 1 1 d . . . . .
F3 F 0.32691(17) 0.56284(9) 0.84896(17) 0.0283(4) Uani 1 1 d . . . . .
F4 F 0.42369(18) 0.45371(9) 0.78768(17) 0.0270(4) Uani 1 1 d . . . . .
C1 C 0.6539(3) 0.48523(13) 0.8685(3) 0.0179(6) Uani 1 1 d . . . . .
C2 C 0.7412(3) 0.53123(13) 0.9265(3) 0.0187(6) Uani 1 1 d . . . . .
C3 C 0.6951(3) 0.58787(13) 0.9593(3) 0.0176(6) Uani 1 1 d . . . . .
C4 C 0.5537(3) 0.59781(13) 0.9305(3) 0.0186(6) Uani 1 1 d . . . . .
C5 C 0.4634(3) 0.55286(14) 0.8726(3) 0.0194(6) Uani 1 1 d . . . . .
C6 C 0.5133(3) 0.49709(14) 0.8417(3) 0.0194(6) Uani 1 1 d . . . . .
N1 N 0.3970(2) 0.24786(10) 0.6811(2) 0.0147(5) Uani 1 1 d . . . . .
C13 C 0.4510(3) 0.26043(15) 0.8111(3) 0.0229(6) Uani 1 1 d . . . . .
H13A H 0.451288 0.305382 0.825384 0.034 Uiso 1 1 calc R U . . .
H13B H 0.545124 0.244317 0.836834 0.034 Uiso 1 1 calc R U . . .
H13C H 0.392165 0.239883 0.856682 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4838(3) 0.28226(12) 0.6181(2) 0.0124(5) Uani 1 1 d . . . . .
H14A H 0.454054 0.273836 0.531992 0.019 Uiso 1 1 calc R U . . .
H14B H 0.579862 0.269186 0.647467 0.019 Uiso 1 1 calc R U . . .
H14C H 0.476013 0.326905 0.632435 0.019 Uiso 1 1 calc R U . . .
C15 C 0.3958(3) 0.17923(14) 0.6569(3) 0.0255(7) Uani 1 1 d . . . . .
H15A H 0.358940 0.171675 0.571196 0.038 Uiso 1 1 calc R U . . .
H15B H 0.337874 0.158216 0.702727 0.038 Uiso 1 1 calc R U . . .
H15C H 0.490001 0.162985 0.681072 0.038 Uiso 1 1 calc R U . . .
C16 C 0.2547(3) 0.27339(16) 0.6400(3) 0.0265(7) Uani 1 1 d . . . . .
H16A H 0.221916 0.266847 0.553486 0.040 Uiso 1 1 calc R U . . .
H16B H 0.255636 0.318030 0.657490 0.040 Uiso 1 1 calc R U . . .
H16C H 0.193213 0.252075 0.681962 0.040 Uiso 1 1 calc R U . . .
I3 I -0.34292(2) 0.35007(2) 0.41095(2) 0.01749(5) Uani 1 1 d . . . . .
I4 I -0.24461(2) 0.60388(2) 0.63571(2) 0.01878(5) Uani 1 1 d . . . . .
F5 F -0.37956(17) 0.48978(8) 0.47542(17) 0.0246(4) Uani 1 1 d . . . . .
F6 F 0.05472(17) 0.54014(8) 0.72158(16) 0.0252(4) Uani 1 1 d . . . . .
F7 F 0.15130(17) 0.42800(8) 0.67541(17) 0.0253(4) Uani 1 1 d . . . . .
F8 F -0.01669(17) 0.34444(8) 0.53886(16) 0.0223(4) Uani 1 1 d . . . . .
C7 C -0.2036(3) 0.41534(13) 0.5060(3) 0.0168(5) Uani 1 1 d . . . . .
C8 C -0.2489(3) 0.47420(13) 0.5271(3) 0.0176(6) Uani 1 1 d . . . . .
C9 C -0.1663(3) 0.51737(12) 0.5999(3) 0.0177(6) Uani 1 1 d . . . . .
C10 C -0.0305(3) 0.50015(13) 0.6509(3) 0.0189(6) Uani 1 1 d . . . . .
C11 C 0.0192(3) 0.44262(13) 0.6291(3) 0.0177(6) Uani 1 1 d . . . . .
C12 C -0.0679(3) 0.40055(13) 0.5579(3) 0.0175(6) Uani 1 1 d . . . . .
I5 I 0.87157(2) 0.25062(2) 0.78682(2) 0.01739(5) 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
I1 C1 2.099(3) . ?
I2 C3 2.089(3) . ?
F1 C2 1.339(3) . ?
F2 C4 1.347(3) . ?
F3 C5 1.343(3) . ?
F4 C6 1.339(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.388(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.389(4) . ?
C4 C5 1.380(4) . ?
C5 C6 1.377(4) . ?
N1 C14 1.456(3) . ?
N1 C13 1.488(4) . ?
N1 C16 1.492(4) . ?
N1 C15 1.501(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
I3 C7 2.093(3) . ?
I4 C9 2.096(3) . ?
F5 C8 1.342(3) . ?
F6 C10 1.340(3) . ?
F7 C11 1.339(3) . ?
F8 C12 1.348(3) . ?
C7 C12 1.383(4) . ?
C7 C8 1.384(4) . ?
C8 C9 1.384(4) . ?
C9 C10 1.394(4) . ?
C10 C11 1.377(4) . ?
C11 C12 1.381(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
C2 C1 C6 117.8(3) . . ?
C2 C1 I1 120.9(2) . . ?
C6 C1 I1 121.3(2) . . ?
F1 C2 C1 118.6(2) . . ?
F1 C2 C3 118.3(3) . . ?
C1 C2 C3 123.2(3) . . ?
C2 C3 C4 117.1(3) . . ?
C2 C3 I2 120.1(2) . . ?
C4 C3 I2 122.8(2) . . ?
F2 C4 C5 118.1(3) . . ?
F2 C4 C3 120.7(3) . . ?
C5 C4 C3 121.3(3) . . ?
F3 C5 C6 120.0(3) . . ?
F3 C5 C4 120.1(3) . . ?
C6 C5 C4 119.9(3) . . ?
F4 C6 C5 118.8(3) . . ?
F4 C6 C1 120.4(3) . . ?
C5 C6 C1 120.8(3) . . ?
C14 N1 C13 106.8(2) . . ?
C14 N1 C16 106.9(2) . . ?
C13 N1 C16 110.1(2) . . ?
C14 N1 C15 112.7(2) . . ?
C13 N1 C15 110.4(2) . . ?
C16 N1 C15 109.8(2) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C7 C8 117.5(3) . . ?
C12 C7 I3 122.3(2) . . ?
C8 C7 I3 120.0(2) . . ?
F5 C8 C9 118.6(2) . . ?
F5 C8 C7 118.3(2) . . ?
C9 C8 C7 123.1(3) . . ?
C8 C9 C10 117.3(3) . . ?
C8 C9 I4 121.1(2) . . ?
C10 C9 I4 121.6(2) . . ?
F6 C10 C11 118.8(3) . . ?
F6 C10 C9 120.0(3) . . ?
C11 C10 C9 121.2(3) . . ?
F7 C11 C10 120.2(3) . . ?
F7 C11 C12 120.3(3) . . ?
C10 C11 C12 119.5(3) . . ?
F8 C12 C11 118.2(2) . . ?
F8 C12 C7 120.4(3) . . ?
C11 C12 C7 121.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 -179.2(3) . . . . ?
I1 C1 C2 F1 2.2(4) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
I1 C1 C2 C3 -178.1(2) . . . . ?
F1 C2 C3 C4 179.1(3) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
F1 C2 C3 I2 -2.1(4) . . . . ?
C1 C2 C3 I2 178.3(2) . . . . ?
C2 C3 C4 F2 179.8(2) . . . . ?
I2 C3 C4 F2 0.9(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
I2 C3 C4 C5 -178.3(2) . . . . ?
F2 C4 C5 F3 -1.3(4) . . . . ?
C3 C4 C5 F3 178.0(3) . . . . ?
F2 C4 C5 C6 -179.6(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
F3 C5 C6 F4 0.4(4) . . . . ?
C4 C5 C6 F4 178.7(3) . . . . ?
F3 C5 C6 C1 -178.1(3) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C2 C1 C6 F4 -178.7(3) . . . . ?
I1 C1 C6 F4 -0.1(4) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
I1 C1 C6 C5 178.3(2) . . . . ?
C12 C7 C8 F5 178.7(2) . . . . ?
I3 C7 C8 F5 -6.4(4) . . . . ?
C12 C7 C8 C9 -2.0(4) . . . . ?
I3 C7 C8 C9 172.8(2) . . . . ?
F5 C8 C9 C10 -179.1(2) . . . . ?
C7 C8 C9 C10 1.6(4) . . . . ?
F5 C8 C9 I4 2.7(4) . . . . ?
C7 C8 C9 I4 -176.5(2) . . . . ?
C8 C9 C10 F6 179.5(3) . . . . ?
I4 C9 C10 F6 -2.4(4) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
I4 C9 C10 C11 178.5(2) . . . . ?
F6 C10 C11 F7 -1.8(4) . . . . ?
C9 C10 C11 F7 177.4(3) . . . . ?
F6 C10 C11 C12 179.1(2) . . . . ?
C9 C10 C11 C12 -1.7(4) . . . . ?
F7 C11 C12 F8 1.4(4) . . . . ?
C10 C11 C12 F8 -179.5(2) . . . . ?
F7 C11 C12 C7 -177.9(3) . . . . ?
C10 C11 C12 C7 1.2(4) . . . . ?
C8 C7 C12 F8 -178.7(2) . . . . ?
I3 C7 C12 F8 6.5(4) . . . . ?
C8 C7 C12 C11 0.6(4) . . . . ?
I3 C7 C12 C11 -174.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13A F2 0.98 2.57 3.184(3) 120.5 3_667
C13 H13C I3 0.98 3.21 4.144(3) 158.9 4_666
C14 H14A I5 0.98 2.79 3.771(3) 179.5 4_565
C14 H14B I5 0.98 3.00 3.959(3) 165.9 .
C14 H14C I1 0.98 3.35 3.926(3) 119.3 .
C15 H15A I1 0.98 3.19 4.128(3) 160.4 4_565
C15 H15B F3 0.98 2.61 3.339(4) 131.4 2_546
C15 H15B I3 0.98 3.33 4.230(3) 154.3 4_666
C15 H15C I4 0.98 3.16 4.064(3) 154.1 2_546
C16 H16B F7 0.98 2.61 3.532(4) 156.6 .

_refine_diff_density_max         0.905
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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_2(13-F4DIB)(NMe4I)_MeOH
_database_code_depnum_ccdc_archive 'CCDC 2040127'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
'bis(1,3-diiodo-2,4,5,6-tetrafluorobenzene) (tetramethylammonium iodide) cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 F4 I2), C4 H12 N, I'
_chemical_formula_sum            'C16 H12 F8 I5 N'
_chemical_formula_weight         1004.77

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

_cell_length_a                   6.9406(6)
_cell_length_b                   20.4866(16)
_cell_length_c                   8.7114(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.802(2)
_cell_angle_gamma                90
_cell_volume                     1216.72(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9743
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.743
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   'not measured'
_exptl_transmission_factor_max   'not measured'
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    6.456
_shelx_estimated_absorpt_T_min   0.509
_shelx_estimated_absorpt_T_max   0.722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_process_details   'Bruker, SADABS'
_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 D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            43360
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_av_R_equivalents  0.0298
_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       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.590
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2581
_reflns_number_gt                2318
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0099P)²+8.0341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2581
_refine_ls_number_parameters     155
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0553
_refine_ls_wR_factor_gt          0.0525
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.222
_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 0.65807(6) 0.750000 1.14432(5) 0.02481(10) Uani 1 2 d S T P . .
I2 I 0.57208(5) 0.60721(2) 0.91733(4) 0.03435(9) Uani 1 1 d . . . . .
I3 I 0.91488(6) 0.35377(2) 0.74707(4) 0.04241(11) Uani 1 1 d . . . . .
F1 F 0.8574(6) 0.4904(2) 0.8932(5) 0.0843(14) Uani 1 1 d . U . . .
F2 F 0.4857(4) 0.35245(14) 0.5230(3) 0.0349(7) Uani 1 1 d . . . . .
F3 F 0.1859(4) 0.43738(17) 0.4916(4) 0.0505(9) Uani 1 1 d . . . . .
F4 F 0.2161(4) 0.54759(15) 0.6627(4) 0.0390(7) Uani 1 1 d . . . . .
N1 N 0.9450(7) 0.250000 0.2716(6) 0.0210(11) Uani 1 2 d S T P . .
C1 C 0.7654(11) 0.250000 0.3390(9) 0.045(2) Uani 1 2 d S T P B .
H1A H 0.733814 0.205168 0.364722 0.067 Uiso 0.5 1 calc R U P A -1
H1B H 0.656524 0.268160 0.262936 0.067 Uiso 0.5 1 calc R U P A -1
H1C H 0.786439 0.276672 0.434025 0.067 Uiso 0.5 1 calc R U P A -1
C2 C 0.9213(15) 0.2837(5) 0.1171(11) 0.036(2) Uani 0.5 1 d . . P B -1
H2A H 1.045382 0.281992 0.078935 0.053 Uiso 0.5 1 calc R U P B -1
H2B H 0.818551 0.261931 0.042089 0.053 Uiso 0.5 1 calc R U P B -1
H2C H 0.884501 0.329372 0.128940 0.053 Uiso 0.5 1 calc R U P B -1
C3 C 1.1204(15) 0.2738(6) 0.3807(12) 0.043(3) Uani 0.5 1 d . . P B -1
H3A H 1.234200 0.272546 0.328965 0.065 Uiso 0.5 1 calc R U P B -1
H3B H 1.098148 0.318704 0.411738 0.065 Uiso 0.5 1 calc R U P B -1
H3C H 1.145073 0.245797 0.473534 0.065 Uiso 0.5 1 calc R U P B -1
C4 C 0.9689(16) 0.1769(5) 0.2439(14) 0.040(3) Uani 0.5 1 d . . P B -1
H4A H 1.085823 0.169704 0.198199 0.060 Uiso 0.5 1 calc R U P B -1
H4B H 0.983119 0.153588 0.343646 0.060 Uiso 0.5 1 calc R U P B -1
H4C H 0.852955 0.160611 0.172230 0.060 Uiso 0.5 1 calc R U P B -1
C5 C 0.5391(7) 0.5213(2) 0.7832(5) 0.0295(10) Uani 1 1 d . . . . .
C6 C 0.6903(8) 0.4768(3) 0.7952(7) 0.0440(15) Uani 1 1 d . . . . .
C7 C 0.6787(8) 0.4191(2) 0.7122(6) 0.0326(11) Uani 1 1 d . . . . .
C8 C 0.5060(7) 0.4067(2) 0.6107(5) 0.0263(10) Uani 1 1 d . . . . .
C9 C 0.3517(7) 0.4495(2) 0.5951(5) 0.0278(10) Uani 1 1 d . . . . .
C10 C 0.3682(7) 0.5063(2) 0.6815(5) 0.0256(9) 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
I2 C5 2.101(5) . ?
I3 C7 2.094(5) . ?
F1 C6 1.335(6) . ?
F2 C8 1.342(5) . ?
F3 C9 1.345(5) . ?
F4 C10 1.338(5) . ?
N1 C1 1.474(9) . ?
N1 C3 1.479(10) . ?
N1 C2 1.494(10) . ?
N1 C4 1.531(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.376(6) . ?
C5 C6 1.379(7) . ?
C6 C7 1.380(7) . ?
C7 C8 1.373(6) . ?
C8 C9 1.371(7) . ?
C9 C10 1.380(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
C1 N1 C3 113.6(6) . . ?
C1 N1 C2 113.6(6) . . ?
C3 N1 C2 111.4(7) . . ?
C1 N1 C4 100.8(5) . . ?
C3 N1 C4 108.8(7) . . ?
C2 N1 C4 107.9(7) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 117.0(4) . . ?
C10 C5 I2 122.4(4) . . ?
C6 C5 I2 120.6(3) . . ?
F1 C6 C5 117.9(4) . . ?
F1 C6 C7 118.1(5) . . ?
C5 C6 C7 123.9(5) . . ?
C8 C7 C6 117.0(5) . . ?
C8 C7 I3 122.7(4) . . ?
C6 C7 I3 120.3(4) . . ?
F2 C8 C9 118.4(4) . . ?
F2 C8 C7 120.4(4) . . ?
C9 C8 C7 121.2(4) . . ?
F3 C9 C8 120.2(4) . . ?
F3 C9 C10 119.6(4) . . ?
C8 C9 C10 120.1(4) . . ?
F4 C10 C5 120.2(4) . . ?
F4 C10 C9 118.9(4) . . ?
C5 C10 C9 120.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C5 C6 F1 -180.0(5) . . . . ?
I2 C5 C6 F1 -0.5(8) . . . . ?
C10 C5 C6 C7 -0.1(9) . . . . ?
I2 C5 C6 C7 179.3(5) . . . . ?
F1 C6 C7 C8 -179.2(6) . . . . ?
C5 C6 C7 C8 1.0(9) . . . . ?
F1 C6 C7 I3 2.2(8) . . . . ?
C5 C6 C7 I3 -177.6(5) . . . . ?
C6 C7 C8 F2 178.2(5) . . . . ?
I3 C7 C8 F2 -3.2(7) . . . . ?
C6 C7 C8 C9 -1.0(8) . . . . ?
I3 C7 C8 C9 177.5(4) . . . . ?
F2 C8 C9 F3 -1.3(7) . . . . ?
C7 C8 C9 F3 178.0(5) . . . . ?
F2 C8 C9 C10 -178.9(4) . . . . ?
C7 C8 C9 C10 0.3(7) . . . . ?
C6 C5 C10 F4 -179.3(5) . . . . ?
I2 C5 C10 F4 1.3(6) . . . . ?
C6 C5 C10 C9 -0.6(7) . . . . ?
I2 C5 C10 C9 179.9(3) . . . . ?
F3 C9 C10 F4 1.5(7) . . . . ?
C8 C9 C10 F4 179.2(4) . . . . ?
F3 C9 C10 C5 -177.2(4) . . . . ?
C8 C9 C10 C5 0.6(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B I2 0.98 3.25 4.131(6) 150.4 3_666
C1 H1C I3 0.98 3.13 4.105(7) 171.8 .
C2 H2A I1 0.98 3.15 4.084(10) 158.9 3_766
C3 H3B F3 0.98 2.57 3.495(11) 157.2 1_655
C4 H4A I2 0.98 3.03 3.980(11) 163.5 2_746
C4 H4B F3 0.98 2.54 3.345(11) 139.7 4_665
C4 H4B F4 0.98 2.57 3.118(11) 115.4 2_646
C4 H4C I2 0.98 3.11 4.016(11) 155.2 2_646

_refine_diff_density_max         1.454
_refine_diff_density_min         -2.200
_refine_diff_density_rms         0.137


# start Validation Reply Form
_vrf_PLAT434_213-F4DIBNMe4I_MeOH 
;
PROBLEM: Short Inter HL..HL Contact F1       ..F1               2.48 Ang.  
RESPONSE: This contact represents and F...F halogen bond, which is discussed
further in the manuscript text.
;
####################################################################### 
# 
# 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_2(13-F4DIB)(NMe4I)_MeCN
_database_code_depnum_ccdc_archive 'CCDC 2040128'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
'bis(1,3-diiodo-2,4,5,6-tetrafluorobenzene) (tetramethylammonium iodide) cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 F4 I2), C4 H12 N, I'
_chemical_formula_sum            'C16 H12 F8 I5 N'
_chemical_formula_weight         1004.77

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.0400(6)
_cell_length_b                   20.5136(10)
_cell_length_c                   12.0201(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.127(2)
_cell_angle_gamma                90
_cell_volume                     2410.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    49168
_cell_measurement_theta_min      1.986
_cell_measurement_theta_max      27.499

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.768
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   'not measured'
_exptl_transmission_factor_max   'not measured'
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.177
_exptl_absorpt_coefficient_mu    6.516
_shelx_estimated_absorpt_T_min   0.292
_shelx_estimated_absorpt_T_max   0.392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.29
_exptl_absorpt_correction_T_max  0.39
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   .
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            40540
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.986
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5504
_reflns_number_gt                5104
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0103P)²+1.0012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5504
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0154
_refine_ls_wR_factor_ref         0.0347
_refine_ls_wR_factor_gt          0.0332
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.003
_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 0.90190(2) 0.24985(2) 0.25656(2) 0.01520(4) Uani 1 1 d . . . . .
I2 I 0.74759(2) 0.38915(2) 0.34248(2) 0.01462(4) Uani 1 1 d . . . . .
I3 I 0.83468(2) 0.64272(2) 0.60126(2) 0.01463(4) Uani 1 1 d . . . . .
I4 I -0.24491(2) 0.60432(2) 0.18656(2) 0.01565(4) Uani 1 1 d . . . . .
I5 I -0.32621(2) 0.34882(2) -0.06495(2) 0.01722(4) Uani 1 1 d . . . . .
F1 F 0.87514(13) 0.50099(6) 0.51439(12) 0.0206(3) Uani 1 1 d . . . . .
F2 F 0.51094(13) 0.64953(6) 0.48143(12) 0.0186(3) Uani 1 1 d . . . . .
F3 F 0.34768(13) 0.56806(6) 0.33494(12) 0.0207(3) Uani 1 1 d . . . . .
F4 F 0.44711(13) 0.45547(6) 0.27191(12) 0.0213(3) Uani 1 1 d . . . . .
F5 F -0.37731(13) 0.48069(6) 0.04998(13) 0.0232(3) Uani 1 1 d . . . . .
F6 F 0.00669(14) 0.35514(6) 0.02111(13) 0.0221(3) Uani 1 1 d . . . . .
F7 F 0.17169(13) 0.44517(7) 0.14396(13) 0.0232(3) Uani 1 1 d . . . . .
F8 F 0.06714(13) 0.55299(7) 0.21988(13) 0.0224(3) Uani 1 1 d . . . . .
N1 N 0.1067(2) 0.75105(8) 0.33496(17) 0.0139(4) Uani 1 1 d . . . . .
C1 C 0.2491(2) 0.72510(12) 0.3685(2) 0.0242(6) Uani 1 1 d . . . . .
H1A H 0.248711 0.678402 0.351283 0.036 Uiso 1 1 calc R U . . .
H1B H 0.285106 0.731817 0.450598 0.036 Uiso 1 1 calc R U . . .
H1C H 0.307098 0.748061 0.325784 0.036 Uiso 1 1 calc R U . . .
C2 C 0.1077(3) 0.82215(11) 0.3614(2) 0.0228(5) Uani 1 1 d . . . . .
H2A H 0.163453 0.845257 0.316923 0.034 Uiso 1 1 calc R U . . .
H2B H 0.146358 0.828886 0.443109 0.034 Uiso 1 1 calc R U . . .
H2C H 0.013940 0.839009 0.341669 0.034 Uiso 1 1 calc R U . . .
C3 C 0.0186(2) 0.71598(12) 0.4010(2) 0.0198(5) Uani 1 1 d . . . . .
H3A H -0.075060 0.732791 0.379031 0.030 Uiso 1 1 calc R U . . .
H3B H 0.054786 0.723008 0.482978 0.030 Uiso 1 1 calc R U . . .
H3C H 0.018581 0.669230 0.384267 0.030 Uiso 1 1 calc R U . . .
C4 C 0.0508(3) 0.74037(11) 0.2102(2) 0.0193(5) Uani 1 1 d . . . . .
H4A H -0.043412 0.756494 0.188838 0.029 Uiso 1 1 calc R U . . .
H4B H 0.052173 0.693686 0.193165 0.029 Uiso 1 1 calc R U . . .
H4C H 0.107116 0.763917 0.166675 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6641(2) 0.47581(10) 0.3920(2) 0.0138(4) Uani 1 1 d . . . . .
C6 C 0.7453(2) 0.51812(10) 0.4687(2) 0.0143(5) Uani 1 1 d . . . . .
C7 C 0.6988(2) 0.57754(10) 0.4990(2) 0.0139(4) Uani 1 1 d . . . . .
C8 C 0.5644(2) 0.59347(10) 0.4523(2) 0.0144(5) Uani 1 1 d . . . . .
C9 C 0.4796(2) 0.55243(10) 0.3770(2) 0.0150(5) Uani 1 1 d . . . . .
C10 C 0.5310(2) 0.49445(10) 0.3463(2) 0.0147(5) Uani 1 1 d . . . . .
C11 C -0.1588(2) 0.51903(10) 0.1360(2) 0.0147(5) Uani 1 1 d . . . . .
C12 C -0.2413(2) 0.47177(11) 0.0728(2) 0.0157(5) Uani 1 1 d . . . . .
C13 C -0.1913(2) 0.41564(10) 0.0330(2) 0.0145(5) Uani 1 1 d . . . . .
C14 C -0.0506(2) 0.40753(11) 0.0593(2) 0.0161(5) Uani 1 1 d . . . . .
C15 C 0.0351(2) 0.45343(11) 0.1225(2) 0.0167(5) Uani 1 1 d . . . . .
C16 C -0.0194(2) 0.50867(11) 0.1599(2) 0.0170(5) 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
I2 C5 2.108(2) . ?
I3 C7 2.097(2) . ?
I4 C11 2.102(2) . ?
I5 C13 2.092(2) . ?
F1 C6 1.341(2) . ?
F2 C8 1.348(2) . ?
F3 C9 1.344(2) . ?
F4 C10 1.344(2) . ?
F5 C12 1.343(3) . ?
F6 C14 1.348(3) . ?
F7 C15 1.347(2) . ?
F8 C16 1.347(3) . ?
N1 C2 1.492(3) . ?
N1 C4 1.493(3) . ?
N1 C1 1.493(3) . ?
N1 C3 1.500(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.378(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.383(3) . ?
C7 C8 1.378(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.380(3) . ?
C11 C16 1.380(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.378(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
C2 N1 C4 109.91(18) . . ?
C2 N1 C1 109.32(18) . . ?
C4 N1 C1 109.70(19) . . ?
C2 N1 C3 109.41(19) . . ?
C4 N1 C3 109.25(18) . . ?
C1 N1 C3 109.24(18) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 117.5(2) . . ?
C10 C5 I2 122.21(16) . . ?
C6 C5 I2 120.24(16) . . ?
F1 C6 C7 118.52(19) . . ?
F1 C6 C5 118.55(19) . . ?
C7 C6 C5 122.9(2) . . ?
C8 C7 C6 117.4(2) . . ?
C8 C7 I3 122.27(16) . . ?
C6 C7 I3 120.18(16) . . ?
F2 C8 C7 120.5(2) . . ?
F2 C8 C9 117.92(19) . . ?
C7 C8 C9 121.6(2) . . ?
F3 C9 C8 120.6(2) . . ?
F3 C9 C10 120.1(2) . . ?
C8 C9 C10 119.3(2) . . ?
F4 C10 C5 120.3(2) . . ?
F4 C10 C9 118.33(19) . . ?
C5 C10 C9 121.4(2) . . ?
C16 C11 C12 117.3(2) . . ?
C16 C11 I4 122.16(16) . . ?
C12 C11 I4 120.48(16) . . ?
F5 C12 C13 118.34(19) . . ?
F5 C12 C11 118.1(2) . . ?
C13 C12 C11 123.6(2) . . ?
C12 C13 C14 116.9(2) . . ?
C12 C13 I5 120.01(16) . . ?
C14 C13 I5 123.10(17) . . ?
F6 C14 C15 118.0(2) . . ?
F6 C14 C13 120.7(2) . . ?
C15 C14 C13 121.3(2) . . ?
F7 C15 C16 120.2(2) . . ?
F7 C15 C14 120.0(2) . . ?
C16 C15 C14 119.8(2) . . ?
F8 C16 C15 118.3(2) . . ?
F8 C16 C11 120.5(2) . . ?
C15 C16 C11 121.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C5 C6 F1 179.9(2) . . . . ?
I2 C5 C6 F1 -3.3(3) . . . . ?
C10 C5 C6 C7 -0.9(3) . . . . ?
I2 C5 C6 C7 175.90(18) . . . . ?
F1 C6 C7 C8 -178.9(2) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
F1 C6 C7 I3 6.0(3) . . . . ?
C5 C6 C7 I3 -173.23(18) . . . . ?
C6 C7 C8 F2 177.6(2) . . . . ?
I3 C7 C8 F2 -7.4(3) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
I3 C7 C8 C9 174.07(18) . . . . ?
F2 C8 C9 F3 -0.4(3) . . . . ?
C7 C8 C9 F3 178.1(2) . . . . ?
F2 C8 C9 C10 -179.5(2) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C6 C5 C10 F4 -179.7(2) . . . . ?
I2 C5 C10 F4 3.5(3) . . . . ?
C6 C5 C10 C9 -1.1(3) . . . . ?
I2 C5 C10 C9 -177.82(18) . . . . ?
F3 C9 C10 F4 1.6(3) . . . . ?
C8 C9 C10 F4 -179.3(2) . . . . ?
F3 C9 C10 C5 -177.1(2) . . . . ?
C8 C9 C10 C5 2.0(4) . . . . ?
C16 C11 C12 F5 179.2(2) . . . . ?
I4 C11 C12 F5 -3.1(3) . . . . ?
C16 C11 C12 C13 -0.2(4) . . . . ?
I4 C11 C12 C13 177.48(18) . . . . ?
F5 C12 C13 C14 -179.2(2) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
F5 C12 C13 I5 2.1(3) . . . . ?
C11 C12 C13 I5 -178.56(18) . . . . ?
C12 C13 C14 F6 -178.1(2) . . . . ?
I5 C13 C14 F6 0.6(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
I5 C13 C14 C15 178.79(18) . . . . ?
F6 C14 C15 F7 0.2(3) . . . . ?
C13 C14 C15 F7 -178.1(2) . . . . ?
F6 C14 C15 C16 177.9(2) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
F7 C15 C16 F8 -1.3(3) . . . . ?
C14 C15 C16 F8 -179.0(2) . . . . ?
F7 C15 C16 C11 178.0(2) . . . . ?
C14 C15 C16 C11 0.3(4) . . . . ?
C12 C11 C16 F8 179.2(2) . . . . ?
I4 C11 C16 F8 1.6(3) . . . . ?
C12 C11 C16 C15 -0.1(3) . . . . ?
I4 C11 C16 C15 -177.71(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A F3 0.98 2.50 3.421(3) 156.9 .
C1 H1C I1 0.98 3.29 4.146(3) 146.8 2_655
C2 H2A F4 0.98 2.64 3.154(3) 113.3 2
C2 H2A F7 0.98 2.61 3.368(3) 134.4 2
C2 H2B I4 0.98 3.19 4.137(3) 162.6 4_676
C2 H2C I2 0.98 3.20 4.080(3) 151.0 2
C3 H3B I1 0.98 3.11 4.071(3) 166.6 3_666
C4 H4C I3 0.98 3.21 4.157(2) 162.3 4_575

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_3(14-F4DIB)2(NMe4I)_UDMH
_database_code_depnum_ccdc_archive 'CCDC 2040125'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
'tris(1,4-diiodo-2,3,5,6-tetrafluorobenzene) bis(tetramethylammonium iodide) cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C6 F4 I2), 2(C4 H12 N), 2(I)'
_chemical_formula_sum            'C26 H24 F12 I8 N2'
_chemical_formula_weight         1607.67

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

_cell_length_a                   11.7588(10)
_cell_length_b                   14.0711(14)
_cell_length_c                   24.608(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4071.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9270
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.623
_exptl_crystal_F_000             2904
_exptl_transmission_factor_min   'not measured'
_exptl_transmission_factor_max   'not measured'
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.223
_exptl_absorpt_coefficient_mu    6.171
_shelx_estimated_absorpt_T_min   0.156
_shelx_estimated_absorpt_T_max   0.340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.18
_exptl_absorpt_correction_T_max  0.34
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   .
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            56179
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         26.425
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8348
_reflns_number_gt                7946
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0265P)²+31.7751P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3358 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.035(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8348
_refine_ls_number_parameters     441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_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 0.33471(6) 0.38585(5) 0.32968(3) 0.02460(16) Uani 1 1 d . . . . .
I2 I 0.12689(6) 0.57389(5) 0.57331(3) 0.02067(15) Uani 1 1 d . . . . .
F1 F 0.2071(6) 0.5794(5) 0.3583(3) 0.0304(16) Uani 1 1 d . . . . .
F2 F 0.1293(6) 0.6523(4) 0.4510(3) 0.0312(16) Uani 1 1 d . . . . .
F3 F 0.2460(5) 0.3760(4) 0.5439(3) 0.0246(14) Uani 1 1 d . . . . .
F4 F 0.3219(6) 0.3017(4) 0.4513(3) 0.0289(15) Uani 1 1 d . . . . .
C1 C 0.2666(9) 0.4370(8) 0.4022(5) 0.023(2) Uani 1 1 d . . . . .
C2 C 0.2180(8) 0.5279(8) 0.4031(5) 0.020(2) Uani 1 1 d . . . . .
C3 C 0.1786(9) 0.5653(7) 0.4516(5) 0.021(2) Uani 1 1 d . . . . .
C4 C 0.1851(9) 0.5166(7) 0.5008(5) 0.018(2) Uani 1 1 d . . . . .
C5 C 0.2348(9) 0.4268(8) 0.4984(5) 0.019(2) Uani 1 1 d . . . . .
C6 C 0.2737(9) 0.3890(7) 0.4497(5) 0.024(2) Uani 1 1 d . . . . .
N1 N 0.6949(8) 0.1652(6) 0.2964(4) 0.0210(19) Uani 1 1 d . . . . .
C19 C 0.6532(13) 0.2192(10) 0.3445(6) 0.040(3) Uani 1 1 d . . . . .
H19A H 0.596947 0.266338 0.332827 0.061 Uiso 1 1 calc R U . . .
H19B H 0.717265 0.251555 0.362021 0.061 Uiso 1 1 calc R U . . .
H19C H 0.617947 0.175192 0.370407 0.061 Uiso 1 1 calc R U . . .
C20 C 0.5996(12) 0.1097(9) 0.2723(6) 0.038(3) Uani 1 1 d . . . . .
H20A H 0.536752 0.152637 0.263398 0.057 Uiso 1 1 calc R U . . .
H20B H 0.573537 0.061988 0.298520 0.057 Uiso 1 1 calc R U . . .
H20C H 0.625934 0.077880 0.239192 0.057 Uiso 1 1 calc R U . . .
C21 C 0.7380(8) 0.2292(7) 0.2544(4) 0.018(2) Uani 1 1 d . . . . .
H21A H 0.805830 0.262056 0.267870 0.026 Uiso 1 1 calc R U . . .
H21B H 0.679358 0.276098 0.245231 0.026 Uiso 1 1 calc R U . . .
H21C H 0.757602 0.192485 0.221874 0.026 Uiso 1 1 calc R U . . .
C22 C 0.7907(11) 0.1008(9) 0.3124(6) 0.038(3) Uani 1 1 d . . . . .
H22A H 0.809923 0.059073 0.281845 0.057 Uiso 1 1 calc R U . . .
H22B H 0.767595 0.062085 0.343629 0.057 Uiso 1 1 calc R U . . .
H22C H 0.857281 0.138989 0.322206 0.057 Uiso 1 1 calc R U . . .
N2 N 0.8774(8) 0.7294(6) 0.3202(5) 0.027(2) Uani 1 1 d . . . . .
C23 C 0.8192(16) 0.6701(14) 0.2825(10) 0.079(7) Uani 1 1 d . . . . .
H23A H 0.737251 0.681904 0.284950 0.118 Uiso 1 1 calc R U . . .
H23B H 0.834768 0.603292 0.291062 0.118 Uiso 1 1 calc R U . . .
H23C H 0.845599 0.684141 0.245616 0.118 Uiso 1 1 calc R U . . .
C24 C 0.8302(16) 0.7158(12) 0.3769(7) 0.058(5) Uani 1 1 d . . . . .
H24A H 0.748626 0.730016 0.376899 0.087 Uiso 1 1 calc R U . . .
H24B H 0.869342 0.758651 0.402075 0.087 Uiso 1 1 calc R U . . .
H24C H 0.842115 0.649830 0.388359 0.087 Uiso 1 1 calc R U . . .
C25 C 0.8603(10) 0.8312(7) 0.3106(5) 0.026(3) Uani 1 1 d . . . . .
H25A H 0.886597 0.847487 0.273994 0.039 Uiso 1 1 calc R U . . .
H25B H 0.903578 0.867739 0.337471 0.039 Uiso 1 1 calc R U . . .
H25C H 0.779265 0.846423 0.313974 0.039 Uiso 1 1 calc R U . . .
C26 C 1.0017(10) 0.7069(12) 0.3183(7) 0.052(4) Uani 1 1 d . . . . .
H26A H 1.031293 0.720734 0.281874 0.077 Uiso 1 1 calc R U . . .
H26B H 1.013273 0.639437 0.326530 0.077 Uiso 1 1 calc R U . . .
H26C H 1.042076 0.745739 0.345106 0.077 Uiso 1 1 calc R U . . .
I3 I 0.54310(6) 0.29753(5) 0.59197(3) 0.02694(17) Uani 1 1 d . . . . .
I4 I 0.50437(6) 0.65023(5) 0.39289(3) 0.02677(17) Uani 1 1 d . . . . .
F5 F 0.6223(6) 0.3044(4) 0.4673(3) 0.0281(15) Uani 1 1 d . . . . .
F6 F 0.6062(6) 0.4380(5) 0.3911(3) 0.0287(15) Uani 1 1 d . . . . .
F7 F 0.4283(6) 0.6428(5) 0.5177(3) 0.0320(17) Uani 1 1 d . . . . .
F8 F 0.4470(6) 0.5094(5) 0.5939(3) 0.0292(15) Uani 1 1 d . . . . .
C7 C 0.5356(9) 0.4028(7) 0.5335(5) 0.021(2) Uani 1 1 d . . . . .
C8 C 0.5750(9) 0.3875(8) 0.4803(5) 0.024(2) Uani 1 1 d . . . . .
C9 C 0.5655(9) 0.4563(8) 0.4409(5) 0.026(2) Uani 1 1 d . . . . .
C10 C 0.5170(9) 0.5432(7) 0.4514(5) 0.022(2) Uani 1 1 d . . . . .
C11 C 0.4776(9) 0.5596(7) 0.5047(5) 0.022(2) Uani 1 1 d . . . . .
C12 C 0.4876(9) 0.4902(8) 0.5437(5) 0.023(2) Uani 1 1 d . . . . .
I5 I 0.67836(8) 0.54850(5) 0.69857(4) 0.03380(19) Uani 1 1 d . . . . .
I6 I 0.89697(6) 0.45401(6) 0.44216(4) 0.03201(19) Uani 1 1 d . . . . .
F9 F 0.8535(7) 0.3895(5) 0.6560(4) 0.0415(19) Uani 1 1 d . . . . .
F10 F 0.9420(6) 0.3572(5) 0.5579(4) 0.0394(19) Uani 1 1 d . . . . .
F11 F 0.7512(6) 0.6270(5) 0.4892(3) 0.0384(18) Uani 1 1 d . . . . .
F12 F 0.6648(7) 0.6605(5) 0.5873(3) 0.0395(18) Uani 1 1 d . . . . .
C13 C 0.7560(12) 0.5245(9) 0.6245(6) 0.036(3) Uani 1 1 d . . . . .
C14 C 0.8252(11) 0.4485(8) 0.6145(6) 0.032(3) Uani 1 1 d . . . . .
C15 C 0.8702(10) 0.4314(8) 0.5638(6) 0.032(3) Uani 1 1 d . . . . .
C16 C 0.8437(10) 0.4877(9) 0.5197(6) 0.031(3) Uani 1 1 d . . . . .
C17 C 0.7751(10) 0.5658(9) 0.5291(6) 0.034(3) Uani 1 1 d . . . . .
C18 C 0.7328(10) 0.5851(8) 0.5811(6) 0.032(3) Uani 1 1 d . . . . .
I7 I -0.02712(8) 0.39003(6) 0.31348(4) 0.0373(2) Uani 1 1 d . . . . .
I8 I 0.46488(6) 0.33828(5) 0.20131(3) 0.02175(15) 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
I1 C1 2.083(13) . ?
I2 C4 2.074(11) . ?
F1 C2 1.324(13) . ?
F2 C3 1.355(11) . ?
F3 C5 1.336(13) . ?
F4 C6 1.353(12) . ?
C1 C6 1.354(17) . ?
C1 C2 1.401(15) . ?
C2 C3 1.386(16) . ?
C3 C4 1.392(16) . ?
C4 C5 1.394(15) . ?
C5 C6 1.387(17) . ?
N1 C21 1.462(13) . ?
N1 C20 1.488(15) . ?
N1 C19 1.491(16) . ?
N1 C22 1.499(15) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N2 C23 1.422(19) . ?
N2 C25 1.466(13) . ?
N2 C26 1.497(14) . ?
N2 C24 1.51(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
I3 C7 2.067(11) . ?
I4 C10 2.089(11) . ?
F5 C8 1.333(13) . ?
F6 C9 1.341(14) . ?
F7 C11 1.345(12) . ?
F8 C12 1.351(14) . ?
C7 C12 1.377(15) . ?
C7 C8 1.404(17) . ?
C8 C9 1.375(18) . ?
C9 C10 1.375(16) . ?
C10 C11 1.410(17) . ?
C11 C12 1.375(16) . ?
I5 C13 2.066(16) . ?
I6 C16 2.063(14) . ?
F9 C14 1.358(14) . ?
F10 C15 1.351(14) . ?
F11 C17 1.336(15) . ?
F12 C18 1.338(13) . ?
C13 C14 1.366(18) . ?
C13 C18 1.395(19) . ?
C14 C15 1.38(2) . ?
C15 C16 1.379(19) . ?
C16 C17 1.383(18) . ?
C17 C18 1.40(2) . ?

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
C6 C1 C2 117.8(11) . . ?
C6 C1 I1 123.0(8) . . ?
C2 C1 I1 119.1(9) . . ?
F1 C2 C3 118.5(9) . . ?
F1 C2 C1 121.7(11) . . ?
C3 C2 C1 119.8(11) . . ?
F2 C3 C2 118.5(10) . . ?
F2 C3 C4 118.6(10) . . ?
C2 C3 C4 122.9(9) . . ?
C3 C4 C5 115.6(10) . . ?
C3 C4 I2 122.5(8) . . ?
C5 C4 I2 121.9(8) . . ?
F3 C5 C6 119.1(9) . . ?
F3 C5 C4 119.4(10) . . ?
C6 C5 C4 121.5(10) . . ?
F4 C6 C1 120.3(11) . . ?
F4 C6 C5 117.4(10) . . ?
C1 C6 C5 122.3(10) . . ?
C21 N1 C20 107.6(9) . . ?
C21 N1 C19 111.2(9) . . ?
C20 N1 C19 109.7(10) . . ?
C21 N1 C22 107.3(9) . . ?
C20 N1 C22 110.7(9) . . ?
C19 N1 C22 110.3(11) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 N2 C25 113.8(12) . . ?
C23 N2 C26 108.9(13) . . ?
C25 N2 C26 109.6(10) . . ?
C23 N2 C24 110.5(14) . . ?
C25 N2 C24 102.8(11) . . ?
C26 N2 C24 111.1(12) . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 H26A 109.5 . . ?
N2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C12 C7 C8 116.3(11) . . ?
C12 C7 I3 122.0(8) . . ?
C8 C7 I3 121.7(8) . . ?
F5 C8 C9 118.8(11) . . ?
F5 C8 C7 119.7(11) . . ?
C9 C8 C7 121.5(11) . . ?
F6 C9 C10 119.4(11) . . ?
F6 C9 C8 118.8(10) . . ?
C10 C9 C8 121.8(12) . . ?
C9 C10 C11 117.3(10) . . ?
C9 C10 I4 122.7(9) . . ?
C11 C10 I4 120.0(8) . . ?
F7 C11 C12 119.3(10) . . ?
F7 C11 C10 120.4(10) . . ?
C12 C11 C10 120.3(10) . . ?
F8 C12 C11 117.8(9) . . ?
F8 C12 C7 119.4(10) . . ?
C11 C12 C7 122.8(11) . . ?
C14 C13 C18 117.2(14) . . ?
C14 C13 I5 123.4(10) . . ?
C18 C13 I5 119.3(10) . . ?
F9 C14 C13 119.3(13) . . ?
F9 C14 C15 118.8(11) . . ?
C13 C14 C15 121.9(12) . . ?
F10 C15 C14 118.2(12) . . ?
F10 C15 C16 120.0(13) . . ?
C14 C15 C16 121.8(11) . . ?
C15 C16 C17 117.1(13) . . ?
C15 C16 I6 121.8(10) . . ?
C17 C16 I6 121.0(11) . . ?
F11 C17 C16 120.8(13) . . ?
F11 C17 C18 118.2(11) . . ?
C16 C17 C18 121.0(12) . . ?
F12 C18 C13 121.0(13) . . ?
F12 C18 C17 118.1(11) . . ?
C13 C18 C17 120.9(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 -179.6(10) . . . . ?
I1 C1 C2 F1 4.8(14) . . . . ?
C6 C1 C2 C3 -0.3(15) . . . . ?
I1 C1 C2 C3 -176.0(8) . . . . ?
F1 C2 C3 F2 1.0(15) . . . . ?
C1 C2 C3 F2 -178.3(9) . . . . ?
F1 C2 C3 C4 179.4(10) . . . . ?
C1 C2 C3 C4 0.2(16) . . . . ?
F2 C3 C4 C5 178.7(9) . . . . ?
C2 C3 C4 C5 0.3(15) . . . . ?
F2 C3 C4 I2 -2.0(14) . . . . ?
C2 C3 C4 I2 179.6(8) . . . . ?
C3 C4 C5 F3 178.9(9) . . . . ?
I2 C4 C5 F3 -0.4(13) . . . . ?
C3 C4 C5 C6 -0.6(15) . . . . ?
I2 C4 C5 C6 -179.9(8) . . . . ?
C2 C1 C6 F4 -178.7(9) . . . . ?
I1 C1 C6 F4 -3.2(15) . . . . ?
C2 C1 C6 C5 0.0(16) . . . . ?
I1 C1 C6 C5 175.5(8) . . . . ?
F3 C5 C6 F4 -0.3(14) . . . . ?
C4 C5 C6 F4 179.2(9) . . . . ?
F3 C5 C6 C1 -179.0(10) . . . . ?
C4 C5 C6 C1 0.5(16) . . . . ?
C12 C7 C8 F5 -179.9(9) . . . . ?
I3 C7 C8 F5 -2.5(13) . . . . ?
C12 C7 C8 C9 -0.3(15) . . . . ?
I3 C7 C8 C9 177.2(8) . . . . ?
F5 C8 C9 F6 -1.4(15) . . . . ?
C7 C8 C9 F6 179.0(9) . . . . ?
F5 C8 C9 C10 179.6(9) . . . . ?
C7 C8 C9 C10 0.0(16) . . . . ?
F6 C9 C10 C11 -178.7(9) . . . . ?
C8 C9 C10 C11 0.3(16) . . . . ?
F6 C9 C10 I4 -0.4(14) . . . . ?
C8 C9 C10 I4 178.7(8) . . . . ?
C9 C10 C11 F7 -179.4(9) . . . . ?
I4 C10 C11 F7 2.3(13) . . . . ?
C9 C10 C11 C12 -0.4(15) . . . . ?
I4 C10 C11 C12 -178.7(8) . . . . ?
F7 C11 C12 F8 -0.1(15) . . . . ?
C10 C11 C12 F8 -179.1(9) . . . . ?
F7 C11 C12 C7 179.1(10) . . . . ?
C10 C11 C12 C7 0.1(17) . . . . ?
C8 C7 C12 F8 179.4(9) . . . . ?
I3 C7 C12 F8 2.0(14) . . . . ?
C8 C7 C12 C11 0.2(16) . . . . ?
I3 C7 C12 C11 -177.2(8) . . . . ?
C18 C13 C14 F9 177.6(11) . . . . ?
I5 C13 C14 F9 -6.0(17) . . . . ?
C18 C13 C14 C15 -0.4(19) . . . . ?
I5 C13 C14 C15 176.0(9) . . . . ?
F9 C14 C15 F10 -0.9(17) . . . . ?
C13 C14 C15 F10 177.1(11) . . . . ?
F9 C14 C15 C16 179.0(10) . . . . ?
C13 C14 C15 C16 -3.0(19) . . . . ?
F10 C15 C16 C17 -176.2(10) . . . . ?
C14 C15 C16 C17 3.8(17) . . . . ?
F10 C15 C16 I6 6.7(15) . . . . ?
C14 C15 C16 I6 -173.3(9) . . . . ?
C15 C16 C17 F11 176.0(11) . . . . ?
I6 C16 C17 F11 -6.9(16) . . . . ?
C15 C16 C17 C18 -1.4(17) . . . . ?
I6 C16 C17 C18 175.7(9) . . . . ?
C14 C13 C18 F12 179.2(11) . . . . ?
I5 C13 C18 F12 2.7(16) . . . . ?
C14 C13 C18 C17 2.7(18) . . . . ?
I5 C13 C18 C17 -173.9(9) . . . . ?
F11 C17 C18 F12 4.1(17) . . . . ?
C16 C17 C18 F12 -178.5(10) . . . . ?
F11 C17 C18 C13 -179.3(11) . . . . ?
C16 C17 C18 C13 -1.8(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C20 H20A I8 0.98 3.14 3.989(13) 145.6 .
C20 H20B I8 0.98 3.18 3.947(12) 136.3 3_645
C20 H20C I1 0.98 3.22 4.101(15) 149.9 3_645
C21 H21A I7 0.98 2.89 3.856(11) 168.0 1_655
C21 H21B I8 0.98 2.88 3.791(10) 155.0 .
C21 H21C F1 0.98 2.57 3.544(13) 172.7 3_645
C22 H22B I2 0.98 3.25 4.202(14) 163.9 4_556
C22 H22C I3 0.98 3.17 4.049(15) 150.5 4_556
C23 H23A I8 0.98 3.26 4.114(17) 147.0 3_655
C23 H23B I5 0.98 3.13 3.705(15) 119.3 2_664
C24 H24A I4 0.98 3.11 3.961(19) 146.2 .
C24 H24B F7 0.98 2.51 3.47(2) 165.4 4_566
C24 H24C I6 0.98 3.12 4.094(16) 170.6 .
C25 H25A I7 0.98 2.78 3.723(12) 161.9 3_655
C25 H25B F8 0.98 2.47 3.405(14) 159.3 4_566
C25 H25C I8 0.98 2.90 3.836(12) 160.7 3_655
C26 H26B F1 0.98 2.55 3.166(15) 120.5 1_655
C26 H26C F12 0.98 2.57 3.54(2) 174.7 4_566

_refine_diff_density_max         3.265
_refine_diff_density_min         -2.127
_refine_diff_density_rms         0.177



# start Validation Reply Form
_vrf_PLAT971_314-F4DIB2NMe4I_UDMH 
;
PROBLEM: Check Calcd Resid. Dens.  0.97A   From I6              3.51 eA-3  
RESPONSE: Due to the proximity to an iodide anion, this residual density
is attributed to slight disorder in the iodide atom position.  This is
common in these systems.
;

_vrf_PLAT434_314-F4DIB2NMe4I_UDMH 
;
PROBLEM: Short Inter HL..HL Contact I5       ..I7               3.45 Ang.  
RESPONSE: This contact represents an I...I halogen bond, which is 
discussed further within the manuscript text.
;
####################################################################### 
# 
# 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_(14-F4DIB)(14-DiMeTetz)
_database_code_depnum_ccdc_archive 'CCDC 2040124'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
'bis(1,4-diiodo-2,3,5,6-tetrafluorobenzene) 1,4-dimethylhexahydro-s-tetrazine cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 0.5(C4 H12 N4)'
_chemical_formula_sum            'C8 H6 F4 I2 N2'
_chemical_formula_weight         459.95

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'
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'
N N 0.0061 0.0033 '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                   8.6391(7)
_cell_length_b                   8.8169(8)
_cell_length_c                   9.5619(8)
_cell_angle_alpha                81.638(3)
_cell_angle_beta                 69.762(3)
_cell_angle_gamma                63.334(3)
_cell_volume                     610.64(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9243
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.502
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   'not measured'
_exptl_transmission_factor_max   'not measured'
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.107
_exptl_absorpt_coefficient_mu    5.175
_shelx_estimated_absorpt_T_min   0.393
_shelx_estimated_absorpt_T_max   0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_T_max  0.61
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   .
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            31433
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.270
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2472
_reflns_number_gt                2426
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+4.0013P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2472
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0196
_refine_ls_wR_factor_ref         0.0560
_refine_ls_wR_factor_gt          0.0559
_refine_ls_goodness_of_fit_ref   1.307
_refine_ls_restrained_S_all      1.307
_refine_ls_shift/su_max          0.000
_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 0.83849(4) 0.21154(4) 0.21521(3) 0.01596(8) Uani 1 1 d . . . . .
F1 F 0.8584(4) 0.5413(4) 0.3005(3) 0.0210(6) Uani 1 1 d . . . . .
F2 F 0.9734(4) 0.7636(3) 0.1365(3) 0.0202(6) Uani 1 1 d . . . . .
C1 C 0.9374(6) 0.3818(5) 0.0874(5) 0.0151(8) Uani 1 1 d . . . . .
C2 C 0.9277(6) 0.5177(6) 0.1516(5) 0.0149(8) Uani 1 1 d . . . . .
C3 C 0.9870(6) 0.6337(5) 0.0666(5) 0.0150(8) Uani 1 1 d . . . . .
N1 N 0.6621(5) -0.0460(5) 0.5329(4) 0.0136(7) Uani 1 1 d . . . . .
N2 N 0.6515(5) 0.0089(5) 0.3852(4) 0.0146(7) Uani 1 1 d . . . . .
C7 C 0.5362(6) -0.1251(6) 0.6037(5) 0.0155(8) Uani 1 1 d . . . . .
H7A H 0.573910 -0.226508 0.544848 0.019 Uiso 1 1 calc R U . . .
H7B H 0.543768 -0.162981 0.704791 0.019 Uiso 1 1 calc R U . . .
C8 C 0.8511(6) -0.1662(6) 0.5196(5) 0.0200(9) Uani 1 1 d . . . . .
H8A H 0.885811 -0.265802 0.461574 0.030 Uiso 1 1 calc R U . . .
H8B H 0.861560 -0.201588 0.619259 0.030 Uiso 1 1 calc R U . . .
H8C H 0.932437 -0.111462 0.469265 0.030 Uiso 1 1 calc R U . . .
H1N2 H 0.684(7) -0.079(6) 0.336(5) 0.007(11) Uiso 1 1 d . . . . .
I2 I 0.59856(4) 0.20666(4) 0.73374(3) 0.01682(8) Uani 1 1 d . . . . .
F3 F 0.7383(4) 0.4943(3) 0.7237(3) 0.0203(6) Uani 1 1 d . . . . .
F4 F 0.3475(4) 0.2774(3) 1.0752(3) 0.0197(5) Uani 1 1 d . . . . .
C4 C 0.6198(6) 0.4943(6) 0.8603(5) 0.0152(8) Uani 1 1 d . . . . .
C5 C 0.5438(6) 0.3795(6) 0.8937(5) 0.0159(9) Uani 1 1 d . . . . .
C6 C 0.4249(6) 0.3868(5) 1.0356(5) 0.0151(8) 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
I1 C1 2.091(4) . ?
F1 C2 1.347(5) . ?
F2 C3 1.348(5) . ?
C1 C2 1.381(6) . ?
C1 C3 1.388(6) 2_765 ?
C2 C3 1.382(6) . ?
N1 N2 1.445(5) . ?
N1 C8 1.466(6) . ?
N1 C7 1.471(5) . ?
N2 C7 1.453(6) 2_656 ?
N2 H1N2 0.85(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
I2 C5 2.102(4) . ?
F3 C4 1.352(5) . ?
F4 C6 1.348(5) . ?
C4 C6 1.383(6) 2_667 ?
C4 C5 1.384(6) . ?
C5 C6 1.379(6) . ?

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
C2 C1 C3 116.5(4) . 2_765 ?
C2 C1 I1 121.7(3) . . ?
C3 C1 I1 121.8(3) 2_765 . ?
F1 C2 C1 120.5(4) . . ?
F1 C2 C3 117.9(4) . . ?
C1 C2 C3 121.7(4) . . ?
F2 C3 C2 118.6(4) . . ?
F2 C3 C1 119.5(4) . 2_765 ?
C2 C3 C1 121.9(4) . 2_765 ?
N2 N1 C8 108.4(3) . . ?
N2 N1 C7 109.3(3) . . ?
C8 N1 C7 111.2(3) . . ?
N1 N2 C7 109.1(3) . 2_656 ?
N1 N2 H1N2 107(3) . . ?
C7 N2 H1N2 110(3) 2_656 . ?
N2 C7 N1 111.9(4) 2_656 . ?
N2 C7 H7A 109.2 2_656 . ?
N1 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 2_656 . ?
N1 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F3 C4 C6 118.2(4) . 2_667 ?
F3 C4 C5 120.6(4) . . ?
C6 C4 C5 121.1(4) 2_667 . ?
C6 C5 C4 117.2(4) . . ?
C6 C5 I2 121.0(3) . . ?
C4 C5 I2 121.8(3) . . ?
F4 C6 C5 120.0(4) . . ?
F4 C6 C4 118.4(4) . 2_667 ?
C5 C6 C4 121.7(4) . 2_667 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 F1 -179.2(4) 2_765 . . . ?
I1 C1 C2 F1 2.0(6) . . . . ?
C3 C1 C2 C3 1.2(7) 2_765 . . . ?
I1 C1 C2 C3 -177.6(3) . . . . ?
F1 C2 C3 F2 0.3(6) . . . . ?
C1 C2 C3 F2 179.9(4) . . . . ?
F1 C2 C3 C1 179.1(4) . . . 2_765 ?
C1 C2 C3 C1 -1.3(7) . . . 2_765 ?
C8 N1 N2 C7 178.7(3) . . . 2_656 ?
C7 N1 N2 C7 57.4(5) . . . 2_656 ?
N2 N1 C7 N2 -59.1(5) . . . 2_656 ?
C8 N1 C7 N2 -178.7(3) . . . 2_656 ?
F3 C4 C5 C6 179.7(4) . . . . ?
C6 C4 C5 C6 -1.2(7) 2_667 . . . ?
F3 C4 C5 I2 -2.6(6) . . . . ?
C6 C4 C5 I2 176.6(3) 2_667 . . . ?
C4 C5 C6 F4 -179.5(4) . . . . ?
I2 C5 C6 F4 2.7(6) . . . . ?
C4 C5 C6 C4 1.2(7) . . . 2_667 ?
I2 C5 C6 C4 -176.6(3) . . . 2_667 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7B F4 0.99 2.49 3.459(5) 164.4 2_657
C8 H8A F1 0.98 2.59 3.519(5) 158.7 1_545
N2 H1N2 F2 0.85(5) 2.48(5) 3.097(5) 130(4) 1_545

_refine_diff_density_max         0.824
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.131

####################################################################### 
# 
# 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_(135-TFTIB)(NMe4I)_UDMH
_database_code_depnum_ccdc_archive 'CCDC 2040131'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
'1,3,5-trifluoro-2,4,6-triiodobenzene tetramethylammonium iodide cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F3 I3, C4 H12 N, I'
_chemical_formula_sum            'C10 H12 F3 I4 N'
_chemical_formula_weight         710.81

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'
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'
N N 0.0061 0.0033 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.3340(2)
_cell_length_b                   21.8848(7)
_cell_length_c                   11.0627(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.8500(10)
_cell_angle_gamma                90
_cell_volume                     1754.46(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.36

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.691
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   'not measured'
_exptl_transmission_factor_max   'not measured'
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.111
_exptl_absorpt_coefficient_mu    7.117
_shelx_estimated_absorpt_T_min   0.124
_shelx_estimated_absorpt_T_max   0.505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31
_exptl_absorpt_correction_T_max  0.51
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   .
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            26043
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.083
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3585
_reflns_number_gt                3421
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0088P)²+5.2639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3585
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0179
_refine_ls_R_factor_gt           0.0166
_refine_ls_wR_factor_ref         0.0387
_refine_ls_wR_factor_gt          0.0380
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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 0.77519(3) 0.54671(2) 0.87148(2) 0.02716(6) Uani 1 1 d . . . . .
I2 I 0.77009(3) 0.57962(2) 0.32916(2) 0.01895(5) Uani 1 1 d . . . . .
I3 I 0.69811(3) 0.32674(2) 0.53043(2) 0.01992(5) Uani 1 1 d . . . . .
F1 F 0.7238(3) 0.40929(9) 0.77262(17) 0.0235(4) Uani 1 1 d . . . . .
F2 F 0.7857(3) 0.60618(9) 0.61384(19) 0.0275(4) Uani 1 1 d . . . . .
F3 F 0.7220(3) 0.43647(9) 0.35201(17) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.7293(4) 0.44641(15) 0.6766(3) 0.0183(6) Uani 1 1 d . . . . .
C2 C 0.7516(4) 0.50881(15) 0.6968(3) 0.0194(6) Uani 1 1 d . . . . .
C3 C 0.7625(4) 0.54562(14) 0.5971(3) 0.0198(6) Uani 1 1 d . . . . .
C4 C 0.7515(4) 0.52280(14) 0.4794(3) 0.0177(6) Uani 1 1 d . . . . .
C5 C 0.7302(4) 0.45997(14) 0.4656(3) 0.0177(6) Uani 1 1 d . . . . .
C6 C 0.7186(4) 0.42079(14) 0.5615(3) 0.0177(6) Uani 1 1 d . . . . .
N1 N 0.7122(4) 0.31155(12) 1.1081(2) 0.0176(5) Uani 1 1 d . . . . .
C7 C 0.7036(5) 0.37218(15) 1.0463(3) 0.0236(7) Uani 1 1 d . . . . .
H7A H 0.810565 0.376899 1.003802 0.035 Uiso 1 1 calc R U . . .
H7B H 0.704455 0.404646 1.107358 0.035 Uiso 1 1 calc R U . . .
H7C H 0.589978 0.374882 0.986886 0.035 Uiso 1 1 calc R U . . .
C8 C 0.5597(4) 0.30906(14) 1.1785(3) 0.0129(6) Uani 1 1 d . . . . .
H8A H 0.442339 0.309924 1.122543 0.019 Uiso 1 1 calc R U . . .
H8B H 0.566448 0.344302 1.233650 0.019 Uiso 1 1 calc R U . . .
H8C H 0.567840 0.271269 1.226561 0.019 Uiso 1 1 calc R U . . .
C9 C 0.8864(5) 0.30662(17) 1.1973(3) 0.0254(7) Uani 1 1 d . . . . .
H9A H 0.992553 0.310850 1.153908 0.038 Uiso 1 1 calc R U . . .
H9B H 0.891107 0.266707 1.237822 0.038 Uiso 1 1 calc R U . . .
H9C H 0.889758 0.339059 1.258656 0.038 Uiso 1 1 calc R U . . .
C10 C 0.7014(5) 0.26139(16) 1.0158(3) 0.0262(7) Uani 1 1 d . . . . .
H10A H 0.582426 0.263384 0.961722 0.039 Uiso 1 1 calc R U . . .
H10B H 0.713045 0.221830 1.057798 0.039 Uiso 1 1 calc R U . . .
H10C H 0.801618 0.266023 0.967246 0.039 Uiso 1 1 calc R U . . .
I4 I 0.82680(3) 0.67715(2) 0.09382(2) 0.01762(5) 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
I1 C2 2.085(3) . ?
I2 C4 2.097(3) . ?
I3 C6 2.088(3) . ?
F1 C1 1.342(4) . ?
F2 C3 1.345(4) . ?
F3 C5 1.351(4) . ?
C1 C6 1.383(4) . ?
C1 C2 1.390(5) . ?
C2 C3 1.379(5) . ?
C3 C4 1.385(5) . ?
C4 C5 1.390(4) . ?
C5 C6 1.376(4) . ?
N1 C8 1.459(4) . ?
N1 C7 1.490(4) . ?
N1 C9 1.493(4) . ?
N1 C10 1.493(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
F1 C1 C6 118.6(3) . . ?
F1 C1 C2 119.0(3) . . ?
C6 C1 C2 122.4(3) . . ?
C3 C2 C1 117.7(3) . . ?
C3 C2 I1 120.2(2) . . ?
C1 C2 I1 122.1(2) . . ?
F2 C3 C2 119.1(3) . . ?
F2 C3 C4 118.2(3) . . ?
C2 C3 C4 122.7(3) . . ?
C3 C4 C5 116.7(3) . . ?
C3 C4 I2 122.0(2) . . ?
C5 C4 I2 121.3(2) . . ?
F3 C5 C6 118.7(3) . . ?
F3 C5 C4 117.8(3) . . ?
C6 C5 C4 123.5(3) . . ?
C5 C6 C1 117.1(3) . . ?
C5 C6 I3 119.9(2) . . ?
C1 C6 I3 122.9(2) . . ?
C8 N1 C7 107.2(2) . . ?
C8 N1 C9 107.1(2) . . ?
C7 N1 C9 109.9(3) . . ?
C8 N1 C10 111.9(3) . . ?
C7 N1 C10 110.3(3) . . ?
C9 N1 C10 110.4(3) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 178.1(3) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
F1 C1 C2 I1 -0.4(4) . . . . ?
C6 C1 C2 I1 -178.2(2) . . . . ?
C1 C2 C3 F2 -179.4(3) . . . . ?
I1 C2 C3 F2 -1.0(4) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
I1 C2 C3 C4 178.7(2) . . . . ?
F2 C3 C4 C5 179.1(3) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
F2 C3 C4 I2 0.0(4) . . . . ?
C2 C3 C4 I2 -179.6(2) . . . . ?
C3 C4 C5 F3 -179.0(3) . . . . ?
I2 C4 C5 F3 0.1(4) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
I2 C4 C5 C6 179.5(2) . . . . ?
F3 C5 C6 C1 179.4(3) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
F3 C5 C6 I3 2.1(4) . . . . ?
C4 C5 C6 I3 -177.3(2) . . . . ?
F1 C1 C6 C5 -178.1(3) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
F1 C1 C6 I3 -0.9(4) . . . . ?
C2 C1 C6 I3 176.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7A I4 0.98 3.24 4.132(3) 151.5 3_766
C7 H7C I4 0.98 3.26 4.104(4) 145.9 3_666
C8 H8A I4 0.98 2.87 3.818(3) 162.2 3_666
C8 H8B F3 0.98 2.57 3.489(4) 155.4 1_556
C8 H8C I4 0.98 2.88 3.837(3) 164.6 2_646
C9 H9A I4 0.98 3.23 4.124(4) 152.0 3_766
C9 H9B I4 0.98 3.28 4.114(4) 143.7 2_646
C10 H10A I4 0.98 3.24 4.104(4) 147.7 3_666
C10 H10C I4 0.98 3.16 4.067(4) 154.4 3_766

_refine_diff_density_max         0.813
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.099


# start Validation Reply Form
_vrf_PLAT434_135-TFTIBNMe4I_UDMH 
;
PROBLEM: Short Inter HL..HL Contact I2       ..I4               3.44 Ang.  
RESPONSE: This contact represents and I...I halogen bond, which is 
discussed in further detail within the manuscript text.
;
####################################################################### 
# 
# 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_2(12-F4DIB)(NMe4I)_MeOH
_database_code_depnum_ccdc_archive 'CCDC 2040130'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
'bis(1,2-diiodo-3,4,5,6-tetrafluorobenzene) (tetramethylammonium iodide) cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C3 F2 I), C4 H12 N, I'
_chemical_formula_sum            'C16 H12 F8 I5 N'
_chemical_formula_weight         1004.77

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           59
_space_group_name_H-M_alt        'P m m n'
_space_group_name_Hall           '-P 2ab 2a'

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

_cell_length_a                   22.6298(11)
_cell_length_b                   6.9472(3)
_cell_length_c                   7.9192(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1245.01(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8190
_cell_measurement_theta_min      3.601
_cell_measurement_theta_max      26.336

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.680
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   'not measured'
_exptl_transmission_factor_max   'not measured'
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    6.309
_shelx_estimated_absorpt_T_min   0.560
_shelx_estimated_absorpt_T_max   0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_process_details   'Bruker, SADABS'
_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 D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            9914
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.601
_diffrn_reflns_theta_max         26.336
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1406
_reflns_number_gt                1189
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0135P)²+1.6568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1406
_refine_ls_number_parameters     93
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0402
_refine_ls_wR_factor_gt          0.0382
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
I1 I 0.250000 0.750000 0.83899(6) 0.02597(13) Uani 1 4 d S T P . .
I2 I 0.37358(2) 0.750000 0.56663(4) 0.02352(10) Uani 1 2 d S T P . .
I3 I 0.38972(2) 0.750000 0.09490(4) 0.02785(11) Uani 1 2 d S T P . .
F1 F 0.52588(14) 0.750000 0.0269(4) 0.0440(9) Uani 1 2 d S T P . .
F2 F 0.62112(13) 0.750000 0.2269(4) 0.0390(8) Uani 1 2 d S T P . .
F3 F 0.60874(13) 0.750000 0.5668(4) 0.0354(8) Uani 1 2 d S T P . .
F4 F 0.50167(13) 0.750000 0.7060(3) 0.0342(8) Uani 1 2 d S T P . .
N1 N 0.750000 0.750000 -0.1908(7) 0.0209(14) Uani 1 4 d S T P . .
C1 C 0.750000 0.5744(8) -0.2981(7) 0.0302(13) Uani 1 2 d S T P . .
H1A H 0.750000 0.459815 -0.225963 0.045 Uiso 1 2 calc R U P . .
H1B H 0.714641 0.573826 -0.369575 0.045 Uiso 0.5 1 calc R U P . .
H1C H 0.785359 0.573826 -0.369575 0.045 Uiso 0.5 1 calc R U P . .
C2 C 0.6969(2) 0.750000 -0.0798(7) 0.0303(13) Uani 1 2 d S T P . .
H2A H 0.697040 0.634063 -0.009315 0.045 Uiso 0.5 1 calc R U P . .
H2B H 0.697521 0.864405 -0.007436 0.045 Uiso 0.5 1 calc R U P . .
H2C H 0.661125 0.751532 -0.149618 0.045 Uiso 1 2 calc R U P . .
C3 C 0.4552(2) 0.750000 0.4389(6) 0.0190(11) Uani 1 2 d S T P . .
C4 C 0.4613(2) 0.750000 0.2628(6) 0.0204(11) Uani 1 2 d S T P . .
C5 C 0.5178(2) 0.750000 0.1945(6) 0.0274(13) Uani 1 2 d S T P . .
C6 C 0.5671(2) 0.750000 0.2952(7) 0.0249(12) Uani 1 2 d S T P . .
C7 C 0.5612(2) 0.750000 0.4678(6) 0.0232(12) Uani 1 2 d S T P . .
C8 C 0.5052(2) 0.750000 0.5365(6) 0.0229(12) Uani 1 2 d S T P . .


_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
I2 C3 2.105(5) . ?
I3 C4 2.095(5) . ?
F1 C5 1.340(5) . ?
F2 C6 1.337(6) . ?
F3 C7 1.331(5) . ?
F4 C8 1.345(5) . ?
N1 C1 1.487(6) 2_665 ?
N1 C1 1.487(6) . ?
N1 C2 1.489(6) . ?
N1 C2 1.489(6) 2_665 ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C8 1.370(7) . ?
C3 C4 1.402(7) . ?
C4 C5 1.390(7) . ?
C5 C6 1.371(7) . ?
C6 C7 1.373(7) . ?
C7 C8 1.379(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
C1 N1 C1 110.3(5) 2_665 . ?
C1 N1 C2 109.72(15) 2_665 . ?
C1 N1 C2 109.72(15) . . ?
C1 N1 C2 109.72(15) 2_665 2_665 ?
C1 N1 C2 109.72(15) . 2_665 ?
C2 N1 C2 107.6(5) . 2_665 ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C3 C4 118.7(4) . . ?
C8 C3 I2 117.0(4) . . ?
C4 C3 I2 124.4(3) . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 I3 117.7(4) . . ?
C3 C4 I3 123.7(3) . . ?
F1 C5 C6 117.8(5) . . ?
F1 C5 C4 120.7(5) . . ?
C6 C5 C4 121.5(5) . . ?
F2 C6 C5 120.5(5) . . ?
F2 C6 C7 119.4(5) . . ?
C5 C6 C7 120.0(5) . . ?
F3 C7 C6 120.5(5) . . ?
F3 C7 C8 120.7(4) . . ?
C6 C7 C8 118.8(5) . . ?
F4 C8 C3 120.9(5) . . ?
F4 C8 C7 116.6(4) . . ?
C3 C8 C7 122.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C3 C4 C5 0.000(1) . . . . ?
I2 C3 C4 C5 180.000(0) . . . . ?
C8 C3 C4 I3 180.000(1) . . . . ?
I2 C3 C4 I3 0.000(1) . . . . ?
C3 C4 C5 F1 180.000(0) . . . . ?
I3 C4 C5 F1 0.000(0) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
I3 C4 C5 C6 180.000(0) . . . . ?
F1 C5 C6 F2 0.000(0) . . . . ?
C4 C5 C6 F2 180.000(0) . . . . ?
F1 C5 C6 C7 180.000(0) . . . . ?
C4 C5 C6 C7 0.000(1) . . . . ?
F2 C6 C7 F3 0.000(0) . . . . ?
C5 C6 C7 F3 180.000(0) . . . . ?
F2 C6 C7 C8 180.000(1) . . . . ?
C5 C6 C7 C8 0.000(1) . . . . ?
C4 C3 C8 F4 180.000(0) . . . . ?
I2 C3 C8 F4 0.000(1) . . . . ?
C4 C3 C8 C7 0.000(1) . . . . ?
I2 C3 C8 C7 180.000(1) . . . . ?
F3 C7 C8 F4 0.000(1) . . . . ?
C6 C7 C8 F4 180.000(1) . . . . ?
F3 C7 C8 C3 180.000(1) . . . . ?
C6 C7 C8 C3 0.000(1) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2B I1 0.98 3.22 4.141(3) 157.3 5_676
C2 H2C F3 0.98 2.54 3.437(6) 152.2 1_554
C2 H2A I1 0.98 3.22 4.141(3) 157.0 5_666

_refine_diff_density_max         0.717
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.134

####################################################################### 
# 
# 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_(135-F3I3B)(NMe4I)_MeOH
_database_code_depnum_ccdc_archive 'CCDC 2040132'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
'(1,3,5-triiodo-2,4,6-trifluorobenzene) (tetramethylammonium iodide) cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F3 I3, C4 H12 N, I'
_chemical_formula_sum            'C10 H12 F3 I4 N'
_chemical_formula_weight         710.81

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   21.6106(13)
_cell_length_b                   7.3407(5)
_cell_length_c                   11.3729(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1804.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    28813
_cell_measurement_theta_min      3.348
_cell_measurement_theta_max      27.495

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.617
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   'not measured'
_exptl_transmission_factor_max   'not measured'
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    6.921
_shelx_estimated_absorpt_T_min   0.358
_shelx_estimated_absorpt_T_max   0.654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_T_max  0.65
_exptl_absorpt_process_details   'Bruker, SADABS'
_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 D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            28813
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.348
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2218
_reflns_number_gt                2124
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0188P)²+2.7518P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2218
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0196
_refine_ls_wR_factor_ref         0.0471
_refine_ls_wR_factor_gt          0.0467
_refine_ls_goodness_of_fit_ref   1.281
_refine_ls_restrained_S_all      1.281
_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 0.66832(2) 0.750000 0.91337(2) 0.02311(8) Uani 1 2 d S T P . .
I2 I 0.57948(2) 0.750000 0.66736(2) 0.02211(8) Uani 1 2 d S T P . .
I3 I 0.32138(2) 0.750000 0.46891(3) 0.02443(8) Uani 1 2 d S T P . .
I4 I 0.54350(2) 0.750000 0.13852(3) 0.03182(9) Uani 1 2 d S T P . .
F1 F 0.43387(12) 0.750000 0.6413(2) 0.0302(6) Uani 1 2 d S T P . .
F2 F 0.40373(12) 0.750000 0.2335(2) 0.0293(6) Uani 1 2 d S T P . .
F3 F 0.60520(12) 0.750000 0.3888(3) 0.0354(6) Uani 1 2 d S T P . .
N1 N 0.31482(17) 0.750000 -0.1164(3) 0.0238(7) Uani 1 2 d S T P . .
C1 C 0.3774(2) 0.750000 -0.0593(4) 0.0302(10) Uani 1 2 d S T P . .
H1A H 0.409572 0.750000 -0.120040 0.045 Uiso 1 2 calc R U P . .
H1B H 0.381797 0.859004 -0.010199 0.045 Uiso 0.5 1 calc R U P . .
H1C H 0.381797 0.640996 -0.010200 0.045 Uiso 0.5 1 calc R U P . .
C2 C 0.30836(16) 0.5834(4) -0.1908(3) 0.0287(7) Uani 1 1 d . . . . .
H2A H 0.340359 0.583698 -0.251842 0.043 Uiso 1 1 calc R U . . .
H2B H 0.313087 0.474703 -0.141544 0.043 Uiso 1 1 calc R U . . .
H2C H 0.267400 0.582405 -0.227750 0.043 Uiso 1 1 calc R U . . .
C3 C 0.2662(2) 0.750000 -0.0233(5) 0.0343(11) Uani 1 2 d S T P . .
H3A H 0.270492 0.859435 0.025373 0.051 Uiso 0.5 1 calc R U P . .
H3B H 0.225166 0.749134 -0.060150 0.051 Uiso 1 2 calc R U P . .
H3C H 0.270853 0.641432 0.026056 0.051 Uiso 0.5 1 calc R U P . .
C4 C 0.52120(19) 0.750000 0.5189(4) 0.0206(8) Uani 1 2 d S T P . .
C5 C 0.45743(19) 0.750000 0.5317(4) 0.0200(8) Uani 1 2 d S T P . .
C6 C 0.41678(18) 0.750000 0.4384(4) 0.0200(8) Uani 1 2 d S T P . .
C7 C 0.44238(19) 0.750000 0.3268(4) 0.0204(8) Uani 1 2 d S T P . .
C8 C 0.5057(2) 0.750000 0.3069(4) 0.0222(8) Uani 1 2 d S T P . .
C9 C 0.54377(18) 0.750000 0.4053(4) 0.0223(8) Uani 1 2 d S T P . .


_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
I2 C4 2.107(4) . ?
I3 C6 2.091(4) . ?
I4 C8 2.082(4) . ?
F1 C5 1.346(5) . ?
F2 C7 1.351(5) . ?
F3 C9 1.341(5) . ?
N1 C3 1.493(6) . ?
N1 C2 1.494(4) . ?
N1 C2 1.494(4) 7_575 ?
N1 C1 1.501(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C9 1.381(6) . ?
C4 C5 1.386(6) . ?
C5 C6 1.377(6) . ?
C6 C7 1.384(6) . ?
C7 C8 1.387(6) . ?
C8 C9 1.389(6) . ?

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
C3 N1 C2 109.6(2) . . ?
C3 N1 C2 109.6(2) . 7_575 ?
C2 N1 C2 110.0(3) . 7_575 ?
C3 N1 C1 109.1(4) . . ?
C2 N1 C1 109.2(2) . . ?
C2 N1 C1 109.2(2) 7_575 . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 C5 116.7(4) . . ?
C9 C4 I2 122.6(3) . . ?
C5 C4 I2 120.7(3) . . ?
F1 C5 C6 118.2(4) . . ?
F1 C5 C4 118.3(4) . . ?
C6 C5 C4 123.6(4) . . ?
C5 C6 C7 116.8(4) . . ?
C5 C6 I3 120.1(3) . . ?
C7 C6 I3 123.1(3) . . ?
F2 C7 C6 118.3(4) . . ?
F2 C7 C8 118.8(4) . . ?
C6 C7 C8 123.0(4) . . ?
C7 C8 C9 116.9(4) . . ?
C7 C8 I4 122.5(3) . . ?
C9 C8 I4 120.6(3) . . ?
F3 C9 C4 118.7(4) . . ?
F3 C9 C8 118.3(4) . . ?
C4 C9 C8 123.0(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C4 C5 F1 180.000(0) . . . . ?
I2 C4 C5 F1 0.000(1) . . . . ?
C9 C4 C5 C6 0.000(1) . . . . ?
I2 C4 C5 C6 180.000(1) . . . . ?
F1 C5 C6 C7 180.000(0) . . . . ?
C4 C5 C6 C7 0.000(1) . . . . ?
F1 C5 C6 I3 0.000(1) . . . . ?
C4 C5 C6 I3 180.000(0) . . . . ?
C5 C6 C7 F2 180.000(0) . . . . ?
I3 C6 C7 F2 0.000(0) . . . . ?
C5 C6 C7 C8 0.000(0) . . . . ?
I3 C6 C7 C8 180.000(0) . . . . ?
F2 C7 C8 C9 180.000(0) . . . . ?
C6 C7 C8 C9 0.000(0) . . . . ?
F2 C7 C8 I4 0.000(0) . . . . ?
C6 C7 C8 I4 180.000(0) . . . . ?
C5 C4 C9 F3 180.000(0) . . . . ?
I2 C4 C9 F3 0.000(1) . . . . ?
C5 C4 C9 C8 0.000(1) . . . . ?
I2 C4 C9 C8 180.000(0) . . . . ?
C7 C8 C9 F3 180.000(0) . . . . ?
I4 C8 C9 F3 0.000(0) . . . . ?
C7 C8 C9 C4 0.000(1) . . . . ?
I4 C8 C9 C4 180.000(0) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B I1 0.98 3.26 4.148(2) 151.6 5_676
C1 H1C I1 0.98 3.26 4.148(2) 151.6 5_666
C2 H2B I1 0.98 3.10 4.025(3) 157.6 5_666
C2 H2C I1 0.98 3.25 4.131(3) 150.6 6_556
C3 H3C I1 0.98 3.23 4.128(3) 152.5 5_666
C3 H3A I1 0.98 3.23 4.128(3) 152.6 5_676

_refine_diff_density_max         0.623
_refine_diff_density_min         -1.150
_refine_diff_density_rms         0.157


# start Validation Reply Form
_vrf_PLAT434_135-F3I3BNMe4I_MeOH 
;
PROBLEM: Short Inter HL..HL Contact I1       ..I2               3.39 Ang.  
RESPONSE: This contact represents and I...I halogen bond, which is
discussed further in the manuscript text.
;
# end Validation Reply Form

#===end
####################################################################### 
# 
# 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_(12-F4DIB)(NMe4I)_UDMH
_database_code_depnum_ccdc_archive 'CCDC 2040129'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
'1,2-diiodo-3,4,5,6-tetrafluorobenzene tetramethylammonium iodide cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C4 H12 N, I'
_chemical_formula_sum            'C10 H12 F4 I3 N'
_chemical_formula_weight         602.91

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.5414(14)
_cell_length_b                   22.618(4)
_cell_length_c                   9.2445(18)
_cell_angle_alpha                90
_cell_angle_beta                 96.641(6)
_cell_angle_gamma                90
_cell_volume                     1566.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9619
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      30.50

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.557
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   'not measured'
_exptl_transmission_factor_max   'not measured'
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    6.011
_shelx_estimated_absorpt_T_min   0.247
_shelx_estimated_absorpt_T_max   0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   .
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            37815
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.394
_diffrn_reflns_theta_max         30.520
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4726
_reflns_number_gt                4333
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0127P)²+2.8448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4726
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0190
_refine_ls_wR_factor_ref         0.0454
_refine_ls_wR_factor_gt          0.0431
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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
I18 I 0.68284(2) 0.42274(2) 0.08756(2) 0.01633(4) Uani 1 1 d . . . . .
I19 I 0.80752(2) 0.57448(2) 0.21615(2) 0.01594(4) Uani 1 1 d . . . . .
I20 I 0.85777(2) 0.32085(2) -0.15256(2) 0.01605(4) Uani 1 1 d . . . . .
F14 F 0.5146(2) 0.61410(6) 0.40726(17) 0.0199(3) Uani 1 1 d . . . . .
F15 F 0.2109(2) 0.56460(7) 0.47518(17) 0.0213(3) Uani 1 1 d . . . . .
F16 F 0.1166(2) 0.45393(7) 0.37926(18) 0.0246(3) Uani 1 1 d . . . . .
F17 F 0.3246(2) 0.39329(7) 0.21604(18) 0.0244(3) Uani 1 1 d . . . . .
N13 N 0.1416(3) 0.72911(9) 0.5996(2) 0.0145(4) Uani 1 1 d . . . . .
C3 C 0.5331(3) 0.47272(10) 0.2213(3) 0.0149(4) Uani 1 1 d . . . . .
C4 C 0.5806(3) 0.52969(10) 0.2696(2) 0.0141(4) Uani 1 1 d . . . . .
C5 C 0.4704(3) 0.55972(10) 0.3545(3) 0.0156(4) Uani 1 1 d . . . . .
C6 C 0.3139(3) 0.53493(11) 0.3911(3) 0.0167(4) Uani 1 1 d . . . . .
C7 C 0.2658(3) 0.47888(11) 0.3424(3) 0.0177(4) Uani 1 1 d . . . . .
C8 C 0.3759(3) 0.44806(10) 0.2587(3) 0.0172(4) Uani 1 1 d . . . . .
C9 C 0.3065(3) 0.69833(10) 0.5796(3) 0.0135(4) Uani 1 1 d . . . . .
H9A H 0.296883 0.681216 0.481605 0.020 Uiso 1 1 calc R U . . .
H9B H 0.327284 0.666748 0.652127 0.020 Uiso 1 1 calc R U . . .
H9C H 0.406330 0.726313 0.591571 0.020 Uiso 1 1 calc R U . . .
C10 C 0.1064(3) 0.78025(11) 0.4970(3) 0.0181(4) Uani 1 1 d . . . . .
H10A H 0.096374 0.765918 0.396386 0.027 Uiso 1 1 calc R U . . .
H10B H 0.204949 0.808601 0.513033 0.027 Uiso 1 1 calc R U . . .
H10C H -0.005312 0.799665 0.514704 0.027 Uiso 1 1 calc R U . . .
C11 C -0.0055(3) 0.68443(11) 0.5762(3) 0.0211(5) Uani 1 1 d . . . . .
H11A H -0.013525 0.669403 0.476278 0.032 Uiso 1 1 calc R U . . .
H11B H -0.118939 0.703050 0.592407 0.032 Uiso 1 1 calc R U . . .
H11C H 0.019537 0.651626 0.644800 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1579(4) 0.75091(11) 0.7530(3) 0.0198(5) Uani 1 1 d . . . . .
H12A H 0.255294 0.779721 0.768139 0.030 Uiso 1 1 calc R U . . .
H12B H 0.183175 0.717559 0.819825 0.030 Uiso 1 1 calc R U . . .
H12C H 0.045730 0.769776 0.771616 0.030 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
I18 C3 2.099(2) . ?
I19 C4 2.096(2) . ?
F14 C5 1.351(3) . ?
F15 C6 1.341(3) . ?
F16 C7 1.338(3) . ?
F17 C8 1.343(3) . ?
N13 C9 1.455(3) . ?
N13 C12 1.493(3) . ?
N13 C11 1.498(3) . ?
N13 C10 1.500(3) . ?
C3 C8 1.390(3) . ?
C3 C4 1.397(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.383(3) . ?
C6 C7 1.380(3) . ?
C7 C8 1.387(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C9 N13 C12 107.53(19) . . ?
C9 N13 C11 106.79(18) . . ?
C12 N13 C11 109.72(19) . . ?
C9 N13 C10 112.37(19) . . ?
C12 N13 C10 109.54(18) . . ?
C11 N13 C10 110.80(19) . . ?
C8 C3 C4 119.0(2) . . ?
C8 C3 I18 117.58(17) . . ?
C4 C3 I18 123.36(17) . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 I19 117.14(17) . . ?
C3 C4 I19 123.81(17) . . ?
F14 C5 C6 117.6(2) . . ?
F14 C5 C4 120.8(2) . . ?
C6 C5 C4 121.6(2) . . ?
F15 C6 C7 120.1(2) . . ?
F15 C6 C5 120.5(2) . . ?
C7 C6 C5 119.5(2) . . ?
F16 C7 C6 120.1(2) . . ?
F16 C7 C8 120.4(2) . . ?
C6 C7 C8 119.5(2) . . ?
F17 C8 C7 117.2(2) . . ?
F17 C8 C3 121.5(2) . . ?
C7 C8 C3 121.3(2) . . ?
N13 C9 H9A 109.5 . . ?
N13 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N13 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N13 C10 H10A 109.5 . . ?
N13 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N13 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N13 C11 H11A 109.5 . . ?
N13 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N13 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N13 C12 H12A 109.5 . . ?
N13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C3 C4 C5 0.6(3) . . . . ?
I18 C3 C4 C5 178.33(17) . . . . ?
C8 C3 C4 I19 -177.53(17) . . . . ?
I18 C3 C4 I19 0.2(3) . . . . ?
C3 C4 C5 F14 177.8(2) . . . . ?
I19 C4 C5 F14 -3.9(3) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
I19 C4 C5 C6 177.49(18) . . . . ?
F14 C5 C6 F15 0.4(3) . . . . ?
C4 C5 C6 F15 179.1(2) . . . . ?
F14 C5 C6 C7 -178.5(2) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
F15 C6 C7 F16 -0.2(4) . . . . ?
C5 C6 C7 F16 178.7(2) . . . . ?
F15 C6 C7 C8 -178.3(2) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
F16 C7 C8 F17 0.8(4) . . . . ?
C6 C7 C8 F17 178.9(2) . . . . ?
F16 C7 C8 C3 -178.9(2) . . . . ?
C6 C7 C8 C3 -0.7(4) . . . . ?
C4 C3 C8 F17 -179.5(2) . . . . ?
I18 C3 C8 F17 2.6(3) . . . . ?
C4 C3 C8 C7 0.1(4) . . . . ?
I18 C3 C8 C7 -177.72(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9A I20 0.98 3.13 4.022(2) 152.1 3_665
C9 H9A F14 0.98 2.39 3.035(3) 122.4 .
C9 H9B I18 0.98 3.15 4.113(2) 167.0 3_666
C9 H9C I20 0.98 2.80 3.762(2) 168.2 2_655
C10 H10A I20 0.98 3.04 3.955(3) 156.2 3_665
C10 H10B I19 0.98 3.28 4.061(3) 137.5 4_576
C10 H10C I18 0.98 3.18 3.919(2) 133.0 2
C10 H10C I20 0.98 3.11 4.040(3) 158.0 2
C11 H11B I20 0.98 3.30 4.184(3) 151.1 2
C11 H11C F16 0.98 2.60 3.278(3) 126.6 3_566
C12 H12B I20 0.98 3.25 4.049(3) 140.4 3_666
C12 H12C I20 0.98 3.32 4.201(3) 150.4 2

_refine_diff_density_max         1.013
_refine_diff_density_min         -1.232
_refine_diff_density_rms         0.127

