# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2173827'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2022-05-20 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT972_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  0.77A   From I1             -2.73 eA-3  
RESPONSE: The maximum and minimum residual electron density peaks of 0.61 and 
2.76 e/ang3 are located 1.35 and 0.83 ang, respectively, from the I1 atom.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N4, C6 F4 I2'
_chemical_formula_sum            'C18 H10 F4 I2 N4'
_chemical_formula_weight         612.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.19820(11)
_cell_length_b                   9.94832(12)
_cell_length_c                   11.70649(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.4133(12)
_cell_angle_gamma                90
_cell_volume                     954.47(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9098
_cell_measurement_theta_min      5.3710
_cell_measurement_theta_max      76.1850

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.130
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.141
_exptl_absorpt_coefficient_mu    26.341
_shelx_estimated_absorpt_T_min   0.088
_shelx_estimated_absorpt_T_max   0.119
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.180
_exptl_absorpt_correction_T_max  0.500
_exptl_absorpt_process_details   'CrysAlisPro (Rigaku OD, 2017)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            11930
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.397
_diffrn_reflns_theta_max         75.231
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1964
_reflns_number_gt                1961
_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       'CrysAlisPro (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2017)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_detail           
;
The maximum and minimum residual electron density peaks of 0.61 and 2.76
e/ang3 are located 1.35 and 0.83 ang, respectively, from the I1 atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+1.4931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1964
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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 0.87684(2) 0.11481(2) 0.72842(2) 0.01001(12) Uani 1 1 d . . . . .
F1 F 0.7901(3) -0.1487(2) 0.86884(18) 0.0153(4) Uani 1 1 d . . . . .
F2 F 1.1198(2) 0.23746(19) 0.92362(17) 0.0158(4) Uani 1 1 d . . . . .
N1 N 0.7384(4) 0.1451(3) 0.4970(3) 0.0117(6) Uani 1 1 d . . . . .
N2 N 0.4972(3) 0.4401(3) 0.4682(2) 0.0121(5) Uani 1 1 d . . . . .
C1 C 0.9530(4) 0.0465(3) 0.8901(3) 0.0102(6) Uani 1 1 d . . . . .
C2 C 0.8954(4) -0.0738(3) 0.9329(3) 0.0091(6) Uani 1 1 d . . . . .
C3 C 1.0599(5) 0.1194(3) 0.9595(3) 0.0101(7) Uani 1 1 d . . . . .
C4 C 0.7614(4) 0.0253(3) 0.4482(3) 0.0157(7) Uani 1 1 d . . . . .
H4 H 0.844907 -0.031058 0.479133 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6704(4) -0.0214(3) 0.3550(3) 0.0152(7) Uani 1 1 d . . . . .
H5 H 0.694253 -0.105739 0.321347 0.018 Uiso 1 1 calc R U . . .
C6 C 0.5439(4) 0.0575(3) 0.3121(3) 0.0136(6) Uani 1 1 d . . . . .
H6 H 0.477808 0.027584 0.249378 0.016 Uiso 1 1 calc R U . . .
C7 C 0.5159(4) 0.1813(3) 0.3628(3) 0.0110(6) Uani 1 1 d . . . . .
H7 H 0.429613 0.237548 0.335734 0.013 Uiso 1 1 calc R U . . .
C8 C 0.6163(4) 0.2212(3) 0.4538(3) 0.0094(6) Uani 1 1 d . . . . .
C9 C 0.5987(4) 0.3530(3) 0.5083(3) 0.0103(6) Uani 1 1 d . . . . .
H9 H 0.663469 0.374099 0.574330 0.012 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.092(3) . ?
F1 C2 1.353(4) . ?
F2 C3 1.344(4) . ?
N1 C4 1.336(4) . ?
N1 C8 1.344(4) . ?
N2 C9 1.283(5) . ?
N2 N2 1.405(5) 3_666 ?
C1 C2 1.385(5) . ?
C1 C3 1.386(5) . ?
C2 C3 1.380(5) 3_757 ?
C4 C5 1.386(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.467(4) . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C8 117.0(3) . . ?
C9 N2 N2 111.5(3) . 3_666 ?
C2 C1 C3 117.2(3) . . ?
C2 C1 I1 120.7(2) . . ?
C3 C1 I1 122.1(3) . . ?
F1 C2 C3 118.4(3) . 3_757 ?
F1 C2 C1 119.6(3) . . ?
C3 C2 C1 121.9(3) 3_757 . ?
F2 C3 C2 118.8(3) . 3_757 ?
F2 C3 C1 120.3(3) . . ?
C2 C3 C1 120.9(3) 3_757 . ?
N1 C4 C5 123.8(3) . . ?
N1 C4 H4 118.1 . . ?
C5 C4 H4 118.1 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C7 118.6(3) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N1 C8 C7 123.3(3) . . ?
N1 C8 C9 114.9(3) . . ?
C7 C8 C9 121.8(3) . . ?
N2 C9 C8 120.9(3) . . ?
N2 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?

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
C3 C1 C2 F1 179.7(3) . . . . ?
I1 C1 C2 F1 0.8(4) . . . . ?
C3 C1 C2 C3 0.7(6) . . . 3_757 ?
I1 C1 C2 C3 -178.2(3) . . . 3_757 ?
C2 C1 C3 F2 -179.6(3) . . . . ?
I1 C1 C3 F2 -0.7(5) . . . . ?
C2 C1 C3 C2 -0.7(5) . . . 3_757 ?
I1 C1 C3 C2 178.2(3) . . . 3_757 ?
C8 N1 C4 C5 1.9(5) . . . . ?
N1 C4 C5 C6 -2.6(6) . . . . ?
C4 C5 C6 C7 1.3(5) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C4 N1 C8 C7 0.0(5) . . . . ?
C4 N1 C8 C9 -178.5(3) . . . . ?
C6 C7 C8 N1 -1.2(5) . . . . ?
C6 C7 C8 C9 177.3(3) . . . . ?
N2 N2 C9 C8 -178.7(3) 3_666 . . . ?
N1 C8 C9 N2 173.4(3) . . . . ?
C7 C8 C9 N2 -5.2(5) . . . . ?

_refine_diff_density_max         0.609
_refine_diff_density_min         -2.765
_refine_diff_density_rms         0.207



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2173832'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2022-05-20 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N4, C6 F4 I2'
_chemical_formula_sum            'C18 H10 F4 I2 N4'
_chemical_formula_weight         612.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.84010(11)
_cell_length_b                   7.44774(7)
_cell_length_c                   11.95687(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.6098(10)
_cell_angle_gamma                90
_cell_volume                     948.826(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9386
_cell_measurement_theta_min      3.7210
_cell_measurement_theta_max      76.1700

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.142
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.081
_exptl_absorpt_coefficient_mu    26.498
_shelx_estimated_absorpt_T_min   0.078
_shelx_estimated_absorpt_T_max   0.223
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.061
_exptl_absorpt_correction_T_max  0.363
_exptl_absorpt_process_details   'CrysAlisPro (Rigaku OD, 2017)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            12110
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.149
_diffrn_reflns_theta_max         75.228
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1958
_reflns_number_gt                1937
_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       'CrysAlisPro (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2017)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_detail           
;
The maximum and minimum residual electron density peaks of 0.70 and 0.91
e/ang3 are located 1.27 and 0.78 ang from the I1 atom, respectively.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+0.8858P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1958
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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 0.20821(2) 0.07618(2) 0.82345(2) 0.01820(9) Uani 1 1 d . . . . .
F1 F 0.30683(18) 0.1204(4) 1.09461(17) 0.0430(6) Uani 1 1 d . . . . .
F2 F 0.4706(2) -0.0670(4) 0.77467(18) 0.0490(7) Uani 1 1 d . . . . .
N1 N -0.0164(2) 0.1432(3) 0.6624(2) 0.0204(5) Uani 1 1 d . . . . .
N2 N -0.4442(2) 0.0371(4) 0.4879(2) 0.0246(5) Uani 1 1 d . . . . .
C1 C 0.3814(3) 0.0294(4) 0.9298(2) 0.0193(5) Uani 1 1 d . . . . .
C2 C 0.4015(3) 0.0607(4) 1.0453(3) 0.0245(7) Uani 1 1 d . . . . .
C3 C 0.4829(3) -0.0318(5) 0.8862(3) 0.0252(6) Uani 1 1 d . . . . .
C4 C 0.0075(3) 0.2170(4) 0.5666(3) 0.0226(6) Uani 1 1 d . . . . .
H4 H 0.089824 0.260303 0.566123 0.027 Uiso 1 1 calc R U . . .
C5 C -0.0817(3) 0.2337(4) 0.4679(3) 0.0239(6) Uani 1 1 d . . . . .
H5 H -0.060463 0.287345 0.401881 0.029 Uiso 1 1 calc R U . . .
C6 C -0.2021(3) 0.1710(4) 0.4669(2) 0.0213(5) Uani 1 1 d . . . . .
H6 H -0.264973 0.180559 0.400371 0.026 Uiso 1 1 calc R U . . .
C7 C -0.2288(3) 0.0936(4) 0.5658(3) 0.0196(6) Uani 1 1 d . . . . .
C8 C -0.1327(3) 0.0811(3) 0.6606(3) 0.0203(6) Uani 1 1 d . . . . .
H8 H -0.150714 0.025770 0.727334 0.024 Uiso 1 1 calc R U . . .
C9 C -0.3540(3) 0.0245(4) 0.5733(2) 0.0207(5) Uani 1 1 d . . . . .
H9 H -0.368079 -0.029670 0.641738 0.025 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.094(3) . ?
F1 C2 1.349(4) . ?
F2 C3 1.341(4) . ?
N1 C4 1.339(4) . ?
N1 C8 1.340(4) . ?
N2 C9 1.280(4) . ?
N2 N2 1.408(5) 3_456 ?
C1 C2 1.379(4) . ?
C1 C3 1.379(4) . ?
C2 C3 1.382(4) 3_657 ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(4) . ?
C7 C9 1.469(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C8 117.2(3) . . ?
C9 N2 N2 111.5(3) . 3_456 ?
C2 C1 C3 116.4(3) . . ?
C2 C1 I1 122.6(2) . . ?
C3 C1 I1 121.0(2) . . ?
F1 C2 C1 120.1(3) . . ?
F1 C2 C3 118.2(3) . 3_657 ?
C1 C2 C3 121.8(3) . 3_657 ?
F2 C3 C1 120.0(3) . . ?
F2 C3 C2 118.1(3) . 3_657 ?
C1 C3 C2 121.8(3) . 3_657 ?
N1 C4 C5 123.4(3) . . ?
N1 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 118.4(3) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C6 C7 C8 118.5(3) . . ?
C6 C7 C9 122.4(3) . . ?
C8 C7 C9 119.2(3) . . ?
N1 C8 C7 123.4(3) . . ?
N1 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
N2 C9 C7 120.2(3) . . ?
N2 C9 H9 119.9 . . ?
C7 C9 H9 119.9 . . ?

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 -179.8(3) . . . . ?
I1 C1 C2 F1 1.4(4) . . . . ?
C3 C1 C2 C3 -0.2(6) . . . 3_657 ?
I1 C1 C2 C3 -178.9(3) . . . 3_657 ?
C2 C1 C3 F2 179.4(3) . . . . ?
I1 C1 C3 F2 -1.8(5) . . . . ?
C2 C1 C3 C2 0.2(6) . . . 3_657 ?
I1 C1 C3 C2 178.9(3) . . . 3_657 ?
C8 N1 C4 C5 0.8(4) . . . . ?
N1 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C5 C6 C7 C9 179.5(3) . . . . ?
C4 N1 C8 C7 -1.5(4) . . . . ?
C6 C7 C8 N1 1.4(4) . . . . ?
C9 C7 C8 N1 -178.8(3) . . . . ?
N2 N2 C9 C7 179.8(3) 3_456 . . . ?
C6 C7 C9 N2 -1.3(5) . . . . ?
C8 C7 C9 N2 178.9(3) . . . . ?

_refine_diff_density_max         0.696
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.140



####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2173837'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2022-05-20 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N4, C6 F4 I2'
_chemical_formula_sum            'C18 H10 F4 I2 N4'
_chemical_formula_weight         612.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   24.5350(4)
_cell_length_b                   4.12409(7)
_cell_length_c                   38.7414(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.1887(17)
_cell_angle_gamma                90
_cell_volume                     3744.95(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14545
_cell_measurement_theta_min      3.7440
_cell_measurement_theta_max      76.2360

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.171
_exptl_crystal_F_000             2304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    26.854
_shelx_estimated_absorpt_T_min   0.043
_shelx_estimated_absorpt_T_max   0.664
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.043
_exptl_absorpt_correction_T_max  0.320
_exptl_absorpt_process_details   'CrysAlisPro (Rigaku OD, 2017)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            23058
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         3.772
_diffrn_reflns_theta_max         75.290
_diffrn_reflns_theta_full        67.684
_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             3857
_reflns_number_gt                3811
_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       'CrysAlisPro (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2017)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_detail           
;
The maximum and minimum residual electron density peaks of 0.92 and 2.29
e/ang3 are located 1.08 and 0.70 ang from the I2 and I1 atoms, respectively.

Owing to poor agreement, two reflections, i.e. (1 5 10) and (-1 5 6), were
omitted from the final cycles of refinement.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+7.2152P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3857
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_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 0.01129(2) 0.02409(6) 0.15478(2) 0.02006(10) Uani 1 1 d . . . . .
I2 I 0.24047(2) 0.61012(6) 0.09893(2) 0.02079(10) Uani 1 1 d . . . . .
F1 F 0.04224(9) -0.0226(6) 0.07978(6) 0.0274(5) Uani 1 1 d . . . . .
F2 F 0.12793(8) 0.2130(6) 0.05842(5) 0.0268(4) Uani 1 1 d . . . . .
F3 F 0.20659(8) 0.6947(6) 0.17306(5) 0.0266(4) Uani 1 1 d . . . . .
F4 F 0.12020(9) 0.4653(6) 0.19422(6) 0.0259(5) Uani 1 1 d . . . . .
N1 N -0.07515(13) -0.2271(9) 0.18121(8) 0.0265(6) Uani 1 1 d . . . . .
N2 N -0.23466(12) -0.2127(9) 0.23784(8) 0.0252(6) Uani 1 1 d . . . . .
N3 N 0.33447(12) 0.7592(9) 0.07326(8) 0.0262(6) Uani 1 1 d . . . . .
N4 N 0.48562(14) 0.4963(9) 0.01329(9) 0.0284(7) Uani 1 1 d . . . . .
C1 C 0.07830(13) 0.2156(9) 0.13767(9) 0.0205(6) Uani 1 1 d . . . . .
C2 C 0.08197(14) 0.1569(10) 0.10333(9) 0.0213(7) Uani 1 1 d . . . . .
C3 C 0.12695(13) 0.2755(9) 0.09233(9) 0.0203(6) Uani 1 1 d . . . . .
C4 C 0.17063(15) 0.4543(9) 0.11530(10) 0.0213(7) Uani 1 1 d . . . . .
C5 C 0.16678(15) 0.5161(9) 0.14958(10) 0.0209(7) Uani 1 1 d . . . . .
C6 C 0.12167(14) 0.3981(9) 0.16052(9) 0.0201(7) Uani 1 1 d . . . . .
C7 C -0.12869(16) -0.1166(10) 0.17005(10) 0.0270(8) Uani 1 1 d . . . . .
H7 H -0.140498 0.000345 0.147960 0.032 Uiso 1 1 calc R U . . .
C8 C -0.16810(15) -0.1639(10) 0.18907(10) 0.0252(7) Uani 1 1 d . . . . .
H8 H -0.205650 -0.078820 0.180284 0.030 Uiso 1 1 calc R U . . .
C9 C -0.15125(14) -0.3390(9) 0.22136(9) 0.0225(7) Uani 1 1 d . . . . .
C10 C -0.09613(16) -0.4591(10) 0.23277(10) 0.0248(7) Uani 1 1 d . . . . .
H10 H -0.083526 -0.583893 0.254279 0.030 Uiso 1 1 calc R U . . .
C11 C -0.05942(15) -0.3941(10) 0.21219(10) 0.0255(8) Uani 1 1 d . . . . .
H11 H -0.021344 -0.472254 0.220583 0.031 Uiso 1 1 calc R U . . .
C12 C -0.19004(15) -0.3887(10) 0.24322(10) 0.0244(7) Uani 1 1 d . . . . .
H12 H -0.182076 -0.551501 0.261377 0.029 Uiso 1 1 calc R U . . .
C13 C 0.38409(16) 0.5972(10) 0.08399(10) 0.0265(8) Uani 1 1 d . . . . .
H13 H 0.394510 0.498138 0.107158 0.032 Uiso 1 1 calc R U . . .
C14 C 0.42080(16) 0.5667(10) 0.06319(10) 0.0256(7) Uani 1 1 d . . . . .
H14 H 0.455553 0.450061 0.071942 0.031 Uiso 1 1 calc R U . . .
C15 C 0.40587(15) 0.7107(10) 0.02897(9) 0.0234(7) Uani 1 1 d . . . . .
C16 C 0.35459(16) 0.8794(11) 0.01767(10) 0.0277(8) Uani 1 1 d . . . . .
H16 H 0.342965 0.979910 -0.005419 0.033 Uiso 1 1 calc R U . . .
C17 C 0.32071(16) 0.8989(11) 0.04053(11) 0.0285(8) Uani 1 1 d . . . . .
H17 H 0.285995 1.017097 0.032646 0.034 Uiso 1 1 calc R U . . .
C18 C 0.44262(15) 0.6821(10) 0.00525(9) 0.0245(7) Uani 1 1 d . . . . .
H18 H 0.433960 0.804836 -0.016446 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.100(3) . ?
I2 C4 2.096(4) . ?
F1 C2 1.344(4) . ?
F2 C3 1.346(4) . ?
F3 C5 1.341(4) . ?
F4 C6 1.346(4) . ?
N1 C7 1.336(5) . ?
N1 C11 1.338(5) . ?
N2 C12 1.278(5) . ?
N2 N2 1.403(6) 7_445 ?
N3 C17 1.342(5) . ?
N3 C13 1.342(5) . ?
N4 C18 1.266(5) . ?
N4 N4 1.410(6) 5_665 ?
C1 C2 1.381(5) . ?
C1 C6 1.388(5) . ?
C2 C3 1.385(5) . ?
C3 C4 1.386(5) . ?
C4 C5 1.383(5) . ?
C5 C6 1.385(5) . ?
C7 C8 1.392(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(5) . ?
C9 C12 1.463(5) . ?
C10 C11 1.394(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.380(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(5) . ?
C15 C18 1.470(5) . ?
C16 C17 1.384(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C11 117.5(3) . . ?
C12 N2 N2 111.7(4) . 7_445 ?
C17 N3 C13 117.3(3) . . ?
C18 N4 N4 111.6(4) . 5_665 ?
C2 C1 C6 117.0(3) . . ?
C2 C1 I1 121.2(3) . . ?
C6 C1 I1 121.8(2) . . ?
F1 C2 C1 120.7(3) . . ?
F1 C2 C3 118.0(3) . . ?
C1 C2 C3 121.3(3) . . ?
F2 C3 C2 118.6(3) . . ?
F2 C3 C4 119.7(3) . . ?
C2 C3 C4 121.7(3) . . ?
C5 C4 C3 117.1(3) . . ?
C5 C4 I2 121.9(3) . . ?
C3 C4 I2 121.0(3) . . ?
F3 C5 C4 120.7(3) . . ?
F3 C5 C6 118.2(3) . . ?
C4 C5 C6 121.1(3) . . ?
F4 C6 C5 118.5(3) . . ?
F4 C6 C1 119.7(3) . . ?
C5 C6 C1 121.8(3) . . ?
N1 C7 C8 123.5(3) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 118.6(3) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 C12 120.4(3) . . ?
C8 C9 C12 121.3(3) . . ?
C9 C10 C11 118.9(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
N1 C11 C10 123.2(3) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N2 C12 C9 119.9(4) . . ?
N2 C12 H12 120.1 . . ?
C9 C12 H12 120.1 . . ?
N3 C13 C14 123.6(3) . . ?
N3 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C13 C14 C15 118.8(4) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 118.0(3) . . ?
C16 C15 C18 120.6(3) . . ?
C14 C15 C18 121.4(3) . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
N3 C17 C16 123.3(4) . . ?
N3 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
N4 C18 C15 121.0(3) . . ?
N4 C18 H18 119.5 . . ?
C15 C18 H18 119.5 . . ?

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
C6 C1 C2 F1 178.8(3) . . . . ?
I1 C1 C2 F1 0.7(5) . . . . ?
C6 C1 C2 C3 0.0(6) . . . . ?
I1 C1 C2 C3 -178.2(3) . . . . ?
F1 C2 C3 F2 1.7(5) . . . . ?
C1 C2 C3 F2 -179.4(3) . . . . ?
F1 C2 C3 C4 -178.0(3) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
F2 C3 C4 C5 178.8(3) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
F2 C3 C4 I2 -3.1(5) . . . . ?
C2 C3 C4 I2 176.7(3) . . . . ?
C3 C4 C5 F3 -178.3(3) . . . . ?
I2 C4 C5 F3 3.6(5) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
I2 C4 C5 C6 -176.9(3) . . . . ?
F3 C5 C6 F4 -0.6(5) . . . . ?
C4 C5 C6 F4 179.9(3) . . . . ?
F3 C5 C6 C1 179.0(3) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
C2 C1 C6 F4 179.5(3) . . . . ?
I1 C1 C6 F4 -2.3(5) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
I1 C1 C6 C5 178.0(3) . . . . ?
C11 N1 C7 C8 0.6(6) . . . . ?
N1 C7 C8 C9 -0.8(6) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C7 C8 C9 C12 178.1(4) . . . . ?
C8 C9 C10 C11 1.6(5) . . . . ?
C12 C9 C10 C11 -176.9(4) . . . . ?
C7 N1 C11 C10 0.6(6) . . . . ?
C9 C10 C11 N1 -1.8(6) . . . . ?
N2 N2 C12 C9 -177.8(4) 7_445 . . . ?
C10 C9 C12 N2 162.2(4) . . . . ?
C8 C9 C12 N2 -16.3(6) . . . . ?
C17 N3 C13 C14 -0.4(6) . . . . ?
N3 C13 C14 C15 -0.2(6) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C13 C14 C15 C18 -178.9(4) . . . . ?
C14 C15 C16 C17 0.2(6) . . . . ?
C18 C15 C16 C17 179.3(4) . . . . ?
C13 N3 C17 C16 0.8(6) . . . . ?
C15 C16 C17 N3 -0.8(7) . . . . ?
N4 N4 C18 C15 179.4(4) 5_665 . . . ?
C16 C15 C18 N4 -171.1(4) . . . . ?
C14 C15 C18 N4 8.0(6) . . . . ?

_refine_diff_density_max         0.919
_refine_diff_density_min         -2.294
_refine_diff_density_rms         0.193



