# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_dabco_12tfib_1-1_HT_253K
_database_code_depnum_ccdc_archive 'CCDC 1990460'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2020-03-15 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C6 H12 N2, C6 F4 I2'
_chemical_formula_sum            'C12 H12 F4 I2 N2'
_chemical_formula_weight         514.04

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   8.4114(6)
_cell_length_b                   11.1190(8)
_cell_length_c                   17.6646(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.661(3)
_cell_angle_gamma                90
_cell_volume                     1605.37(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    253.0(1)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.27

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.952
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.126
_exptl_absorpt_coefficient_mu    3.949
_shelx_estimated_absorpt_T_min   0.117
_shelx_estimated_absorpt_T_max   0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3087
_exptl_absorpt_correction_T_max  0.7099
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'

_diffrn_ambient_temperature      253.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Mo)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 CMOS
_diffrn_detector_type            'PHOTON 100'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            31566
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         31.057
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2562
_reflns_number_gt                2181
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          
'Refined as a 2-component twin. Batch scale factor 0.1371(5).,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0234P)²+0.8452P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.00305(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2562
_refine_ls_number_parameters     120
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0504
_refine_ls_wR_factor_gt          0.0467
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.037
_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
C1S C 0.0563(3) 0.6916(2) 0.28588(14) 0.0506(5) Uani 1 1 d . . . . .
C2S C 0.1099(4) 0.8011(3) 0.31932(17) 0.0625(7) Uani 1 1 d . . . . .
C3S C 0.0566(4) 0.9083(2) 0.28462(17) 0.0667(7) Uani 1 1 d . . . . .
F1S F 0.2161(3) 0.80658(19) 0.38928(12) 0.0919(6) Uani 1 1 d . . . . .
F2S F 0.1112(4) 1.01295(17) 0.31797(15) 0.1019(7) Uani 1 1 d . . . . .
I1S I 0.13833(2) 0.53480(2) 0.35146(2) 0.06069(8) Uani 1 1 d . . . . .
N1A N 0.2228(3) 0.33736(18) 0.45178(11) 0.0527(5) Uani 1 1 d D U . . .
C1A C 0.1827(9) 0.2253(4) 0.4111(3) 0.0594(13) Uani 0.5 1 d D U P A -1
H1A1 H 0.248334 0.215485 0.373177 0.071 Uiso 0.5 1 calc R U P A -1
H1A2 H 0.068335 0.225326 0.383629 0.071 Uiso 0.5 1 calc R U P A -1
C2A C 0.2159(8) 0.1210(4) 0.4697(3) 0.0605(13) Uani 0.5 1 d D U P A -1
H2A1 H 0.115293 0.076483 0.466541 0.073 Uiso 0.5 1 calc R U P A -1
H2A2 H 0.294918 0.066632 0.456088 0.073 Uiso 0.5 1 calc R U P A -1
C3A C 0.3928(7) 0.3404(6) 0.4967(3) 0.0675(14) Uani 0.5 1 d D U P A -1
H3A1 H 0.413970 0.415419 0.525347 0.081 Uiso 0.5 1 calc R U P A -1
H3A2 H 0.465840 0.335796 0.461687 0.081 Uiso 0.5 1 calc R U P A -1
C4A C 0.4247(7) 0.2339(5) 0.5537(4) 0.0686(14) Uani 0.5 1 d D U P A -1
H4A1 H 0.509990 0.183320 0.542213 0.082 Uiso 0.5 1 calc R U P A -1
H4A2 H 0.462522 0.263807 0.606488 0.082 Uiso 0.5 1 calc R U P A -1
C5A C 0.1204(7) 0.3523(5) 0.5093(3) 0.0574(11) Uani 0.5 1 d D U P A -1
H5A1 H 0.005613 0.353744 0.482515 0.069 Uiso 0.5 1 calc R U P A -1
H5A2 H 0.146720 0.427914 0.536828 0.069 Uiso 0.5 1 calc R U P A -1
C6A C 0.1532(8) 0.2473(5) 0.5675(3) 0.0618(12) Uani 0.5 1 d D U P A -1
H6A1 H 0.193377 0.278277 0.619878 0.074 Uiso 0.5 1 calc R U P A -1
H6A2 H 0.052034 0.204335 0.565744 0.074 Uiso 0.5 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1S C2S 1.381(4) . ?
C1S C1S 1.392(5) 2 ?
C1S I1S 2.117(2) . ?
C2S F1S 1.345(3) . ?
C2S C3S 1.367(4) . ?
C3S F2S 1.335(3) . ?
C3S C3S 1.361(6) 2 ?
N1A C1A 1.438(5) . ?
N1A C3A 1.463(5) . ?
N1A C5A 1.488(5) . ?
C1A C2A 1.536(6) . ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A C4A 1.538(7) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A C6A 1.538(6) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?

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
C2S C1S C1S 118.20(16) . 2 ?
C2S C1S I1S 117.43(19) . . ?
C1S C1S I1S 124.21(7) 2 . ?
F1S C2S C3S 116.6(2) . . ?
F1S C2S C1S 120.8(3) . . ?
C3S C2S C1S 122.5(3) . . ?
F2S C3S C3S 119.41(18) . 2 ?
F2S C3S C2S 121.3(3) . . ?
C3S C3S C2S 119.24(16) 2 . ?
C1A N1A C3A 112.0(4) . . ?
C1A N1A C5A 109.4(4) . . ?
C3A N1A C5A 106.1(3) . . ?
N1A C1A C2A 109.5(4) . . ?
N1A C1A H1A1 109.8 . . ?
C2A C1A H1A1 109.8 . . ?
N1A C1A H1A2 109.8 . . ?
C2A C1A H1A2 109.8 . . ?
H1A1 C1A H1A2 108.2 . . ?
N1A C2A C1A 111.9(4) 7_556 . ?
N1A C2A H2A1 109.2 7_556 . ?
C1A C2A H2A1 109.2 . . ?
N1A C2A H2A2 109.2 7_556 . ?
C1A C2A H2A2 109.2 . . ?
H2A1 C2A H2A2 107.9 . . ?
N1A C3A C4A 109.5(4) . . ?
N1A C3A H3A1 109.8 . . ?
C4A C3A H3A1 109.8 . . ?
N1A C3A H3A2 109.8 . . ?
C4A C3A H3A2 109.8 . . ?
H3A1 C3A H3A2 108.2 . . ?
N1A C4A C3A 111.2(4) 7_556 . ?
N1A C4A H4A1 109.4 7_556 . ?
C3A C4A H4A1 109.4 . . ?
N1A C4A H4A2 109.4 7_556 . ?
C3A C4A H4A2 109.4 . . ?
H4A1 C4A H4A2 108.0 . . ?
N1A C5A C6A 109.3(4) . . ?
N1A C5A H5A1 109.8 . . ?
C6A C5A H5A1 109.8 . . ?
N1A C5A H5A2 109.8 . . ?
C6A C5A H5A2 109.8 . . ?
H5A1 C5A H5A2 108.3 . . ?
N1A C6A C5A 110.4(4) 7_556 . ?
N1A C6A H6A1 109.6 7_556 . ?
C5A C6A H6A1 109.6 . . ?
N1A C6A H6A2 109.6 7_556 . ?
C5A C6A H6A2 109.6 . . ?
H6A1 C6A H6A2 108.1 . . ?

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
C1S C1S C2S F1S 178.6(3) 2 . . . ?
I1S C1S C2S F1S 3.1(4) . . . . ?
C1S C1S C2S C3S -0.1(6) 2 . . . ?
I1S C1S C2S C3S -175.6(3) . . . . ?
F1S C2S C3S F2S 1.7(5) . . . . ?
C1S C2S C3S F2S -179.5(3) . . . . ?
F1S C2S C3S C3S -177.1(4) . . . 2 ?
C1S C2S C3S C3S 1.7(6) . . . 2 ?
C3A N1A C1A C2A 57.3(6) . . . . ?
C5A N1A C1A C2A -60.0(6) . . . . ?
N1A C1A C2A N1A 0.0(7) . . . 7_556 ?
C1A N1A C3A C4A -56.5(6) . . . . ?
C5A N1A C3A C4A 62.8(6) . . . . ?
N1A C3A C4A N1A -1.4(8) . . . 7_556 ?
C1A N1A C5A C6A 59.6(5) . . . . ?
C3A N1A C5A C6A -61.4(5) . . . . ?
N1A C5A C6A N1A -0.2(6) . . . 7_556 ?

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.069


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: nitromethane'
####################################################################### 
# 
# 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_dabco_12tfib_1-2_253K
_database_code_depnum_ccdc_archive 'CCDC 1990461'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2020-03-15 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         '2(C6 F4 I2), C6 H12 N2'
_chemical_formula_sum            'C18 H12 F8 I4 N2'
_chemical_formula_weight         915.90

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                   7.5107(5)
_cell_length_b                   12.8506(8)
_cell_length_c                   13.4853(9)
_cell_angle_alpha                94.235(2)
_cell_angle_beta                 102.514(2)
_cell_angle_gamma                102.883(2)
_cell_volume                     1228.41(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    253.0(1)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      31.88

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.476
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.873
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.202
_exptl_absorpt_coefficient_mu    5.143
_shelx_estimated_absorpt_T_min   0.094
_shelx_estimated_absorpt_T_max   0.423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0749
_exptl_absorpt_correction_T_max  0.4792
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'

_diffrn_ambient_temperature      253.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Mo)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 CMOS
_diffrn_detector_type            'PHOTON 100'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            50538
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.089
_diffrn_reflns_theta_max         34.771
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             9734
_reflns_number_gt                6950
_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 APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_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)+(0.0266P)²+1.6074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.0230(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9734
_refine_ls_number_parameters     363
_refine_ls_number_restraints     501
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.008
_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
C1S C 0.4389(4) 0.2257(2) 0.2629(3) 0.0396(6) Uani 1 1 d . . . . .
C2S C 0.4489(4) 0.2149(3) 0.3665(3) 0.0426(6) Uani 1 1 d . . . . .
C3S C 0.3918(5) 0.1128(3) 0.3938(3) 0.0483(7) Uani 1 1 d . . . . .
C4S C 0.3262(5) 0.0244(3) 0.3226(3) 0.0499(8) Uani 1 1 d . . . . .
C5S C 0.3173(5) 0.0336(3) 0.2218(3) 0.0473(7) Uani 1 1 d . . . . .
C6S C 0.3730(5) 0.1338(3) 0.1927(3) 0.0448(7) Uani 1 1 d . . . . .
F1S F 0.3991(4) 0.0990(2) 0.49218(18) 0.0708(6) Uani 1 1 d . . . . .
F2S F 0.2684(4) -0.07445(18) 0.3502(2) 0.0754(7) Uani 1 1 d . . . . .
F3S F 0.2540(4) -0.05380(17) 0.1520(2) 0.0699(6) Uani 1 1 d . . . . .
F4S F 0.3615(4) 0.13926(19) 0.09285(17) 0.0698(6) Uani 1 1 d . . . . .
I1S I 0.51549(3) 0.37608(2) 0.21026(2) 0.04945(7) Uani 1 1 d . . . . .
I2S I 0.55145(5) 0.34429(2) 0.48118(2) 0.07121(10) Uani 1 1 d . . . . .
C1T C 0.9089(4) 1.1842(2) 0.2264(3) 0.0413(6) Uani 1 1 d . . . . .
C2T C 0.9581(4) 1.2347(2) 0.3270(3) 0.0424(6) Uani 1 1 d . . . . .
C3T C 1.0287(4) 1.3455(3) 0.3461(3) 0.0507(8) Uani 1 1 d . . . . .
C4T C 1.0508(5) 1.4056(3) 0.2684(4) 0.0565(9) Uani 1 1 d . . . . .
C5T C 1.0032(5) 1.3580(3) 0.1707(3) 0.0551(9) Uani 1 1 d . . . . .
C6T C 0.9324(5) 1.2477(3) 0.1497(3) 0.0474(7) Uani 1 1 d . . . . .
F1T F 1.0749(4) 1.3969(2) 0.4426(2) 0.0769(7) Uani 1 1 d . . . . .
F2T F 1.1206(4) 1.51323(17) 0.2898(3) 0.0855(8) Uani 1 1 d . . . . .
F3T F 1.0224(4) 1.4173(2) 0.0940(2) 0.0817(8) Uani 1 1 d . . . . .
F4T F 0.8881(4) 1.2037(2) 0.05176(18) 0.0692(6) Uani 1 1 d . . . . .
I1T I 0.80568(3) 1.01583(2) 0.18743(2) 0.05078(8) Uani 1 1 d . . . . .
I2T I 0.93151(4) 1.15030(2) 0.45106(2) 0.06469(9) Uani 1 1 d . . . . .
C1A C 0.752(2) 0.6178(11) 0.1065(9) 0.057(2) Uani 0.53(2) 1 d D U P A 1
H1A1 H 0.689340 0.582187 0.037839 0.068 Uiso 0.53(2) 1 calc R U P A 1
H1A2 H 0.864150 0.592383 0.129498 0.068 Uiso 0.53(2) 1 calc R U P A 1
C2A C 0.8070(19) 0.7403(11) 0.1047(10) 0.051(2) Uani 0.53(2) 1 d D U P A 1
H2A1 H 0.941851 0.767247 0.130757 0.062 Uiso 0.53(2) 1 calc R U P A 1
H2A2 H 0.774070 0.756148 0.034768 0.062 Uiso 0.53(2) 1 calc R U P A 1
C3A C 0.4562(14) 0.6269(10) 0.1366(13) 0.067(3) Uani 0.53(2) 1 d D U P A 1
H3A1 H 0.371960 0.611027 0.181734 0.080 Uiso 0.53(2) 1 calc R U P A 1
H3A2 H 0.391989 0.588522 0.069140 0.080 Uiso 0.53(2) 1 calc R U P A 1
C4A C 0.5050(17) 0.7484(10) 0.1303(12) 0.058(3) Uani 0.53(2) 1 d D U P A 1
H4A1 H 0.465582 0.761291 0.059845 0.070 Uiso 0.53(2) 1 calc R U P A 1
H4A2 H 0.438294 0.783620 0.171018 0.070 Uiso 0.53(2) 1 calc R U P A 1
C5A C 0.721(2) 0.6486(7) 0.2767(6) 0.063(2) Uani 0.53(2) 1 d D U P A 1
H5A1 H 0.836796 0.627113 0.301599 0.076 Uiso 0.53(2) 1 calc R U P A 1
H5A2 H 0.641122 0.630152 0.323714 0.076 Uiso 0.53(2) 1 calc R U P A 1
C6A C 0.766(2) 0.7707(7) 0.2739(6) 0.059(2) Uani 0.53(2) 1 d D U P A 1
H6A1 H 0.699326 0.803452 0.316779 0.071 Uiso 0.53(2) 1 calc R U P A 1
H6A2 H 0.899477 0.801347 0.300487 0.071 Uiso 0.53(2) 1 calc R U P A 1
N1A N 0.6260(15) 0.5904(8) 0.1750(8) 0.053(2) Uani 0.53(2) 1 d D U P A 1
N2A N 0.7080(17) 0.7936(8) 0.1681(8) 0.048(2) Uani 0.53(2) 1 d D U P A 1
C1A' C 0.7737(19) 0.6277(12) 0.1312(13) 0.061(3) Uani 0.47(2) 1 d D U P A 2
H1A3 H 0.758076 0.591312 0.063115 0.073 Uiso 0.47(2) 1 calc R U P A 2
H1A4 H 0.876985 0.608600 0.176774 0.073 Uiso 0.47(2) 1 calc R U P A 2
C2A' C 0.821(2) 0.7502(13) 0.1290(13) 0.056(3) Uani 0.47(2) 1 d D U P A 2
H2A3 H 0.946284 0.782398 0.171174 0.067 Uiso 0.47(2) 1 calc R U P A 2
H2A4 H 0.818785 0.765441 0.059399 0.067 Uiso 0.47(2) 1 calc R U P A 2
C3A' C 0.4487(15) 0.6255(10) 0.0996(9) 0.054(2) Uani 0.47(2) 1 d D U P A 2
H3A3 H 0.334153 0.603096 0.122890 0.065 Uiso 0.47(2) 1 calc R U P A 2
H3A4 H 0.426611 0.590647 0.030271 0.065 Uiso 0.47(2) 1 calc R U P A 2
C4A' C 0.4962(18) 0.7480(10) 0.1000(10) 0.050(2) Uani 0.47(2) 1 d D U P A 2
H4A3 H 0.494828 0.764995 0.030974 0.059 Uiso 0.47(2) 1 calc R U P A 2
H4A4 H 0.402373 0.777462 0.123729 0.059 Uiso 0.47(2) 1 calc R U P A 2
C5A' C 0.630(3) 0.6462(9) 0.2696(7) 0.068(3) Uani 0.47(2) 1 d D U P A 2
H5A3 H 0.730173 0.624910 0.315612 0.082 Uiso 0.47(2) 1 calc R U P A 2
H5A4 H 0.515961 0.624542 0.293518 0.082 Uiso 0.47(2) 1 calc R U P A 2
C6A' C 0.681(3) 0.7688(8) 0.2709(7) 0.067(3) Uani 0.47(2) 1 d D U P A 2
H6A3 H 0.590191 0.799211 0.296609 0.080 Uiso 0.47(2) 1 calc R U P A 2
H6A4 H 0.804138 0.799287 0.316397 0.080 Uiso 0.47(2) 1 calc R U P A 2
N1A' N 0.6011(17) 0.5919(8) 0.1660(8) 0.052(2) Uani 0.47(2) 1 d D U P A 2
N2A' N 0.6829(19) 0.7966(9) 0.1675(8) 0.049(2) Uani 0.47(2) 1 d D U P A 2


_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
C1S C6S 1.381(4) . ?
C1S C2S 1.401(5) . ?
C1S I1S 2.111(3) . ?
C2S C3S 1.389(5) . ?
C2S I2S 2.070(3) . ?
C3S F1S 1.343(4) . ?
C3S C4S 1.355(5) . ?
C4S F2S 1.354(4) . ?
C4S C5S 1.362(5) . ?
C5S F3S 1.336(4) . ?
C5S C6S 1.376(4) . ?
C6S F4S 1.339(4) . ?
C1T C6T 1.380(5) . ?
C1T C2T 1.395(5) . ?
C1T I1T 2.113(3) . ?
C2T C3T 1.388(4) . ?
C2T I2T 2.081(3) . ?
C3T F1T 1.351(4) . ?
C3T C4T 1.364(6) . ?
C4T C5T 1.348(6) . ?
C4T F2T 1.350(4) . ?
C5T F3T 1.343(4) . ?
C5T C6T 1.383(5) . ?
C6T F4T 1.338(4) . ?
C1A N1A 1.465(6) . ?
C1A C2A 1.539(7) . ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
C2A N2A 1.474(6) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A N1A 1.460(7) . ?
C3A C4A 1.535(7) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A N2A 1.465(6) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A N1A 1.462(6) . ?
C5A C6A 1.535(7) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6A N2A 1.470(6) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C1A' N1A' 1.463(7) . ?
C1A' C2A' 1.538(7) . ?
C1A' H1A3 0.9700 . ?
C1A' H1A4 0.9700 . ?
C2A' N2A' 1.471(7) . ?
C2A' H2A3 0.9700 . ?
C2A' H2A4 0.9700 . ?
C3A' N1A' 1.461(7) . ?
C3A' C4A' 1.534(7) . ?
C3A' H3A3 0.9700 . ?
C3A' H3A4 0.9700 . ?
C4A' N2A' 1.469(7) . ?
C4A' H4A3 0.9700 . ?
C4A' H4A4 0.9700 . ?
C5A' N1A' 1.464(7) . ?
C5A' C6A' 1.535(7) . ?
C5A' H5A3 0.9700 . ?
C5A' H5A4 0.9700 . ?
C6A' N2A' 1.466(7) . ?
C6A' H6A3 0.9700 . ?
C6A' H6A4 0.9700 . ?

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
C6S C1S C2S 118.2(3) . . ?
C6S C1S I1S 119.1(2) . . ?
C2S C1S I1S 122.7(2) . . ?
C3S C2S C1S 118.7(3) . . ?
C3S C2S I2S 118.5(3) . . ?
C1S C2S I2S 122.8(2) . . ?
F1S C3S C4S 117.9(3) . . ?
F1S C3S C2S 120.6(3) . . ?
C4S C3S C2S 121.5(3) . . ?
F2S C4S C3S 120.9(3) . . ?
F2S C4S C5S 118.7(3) . . ?
C3S C4S C5S 120.4(3) . . ?
F3S C5S C4S 120.3(3) . . ?
F3S C5S C6S 120.5(3) . . ?
C4S C5S C6S 119.2(3) . . ?
F4S C6S C5S 117.3(3) . . ?
F4S C6S C1S 120.7(3) . . ?
C5S C6S C1S 121.9(3) . . ?
C6T C1T C2T 118.0(3) . . ?
C6T C1T I1T 119.1(2) . . ?
C2T C1T I1T 122.9(2) . . ?
C3T C2T C1T 119.2(3) . . ?
C3T C2T I2T 118.2(3) . . ?
C1T C2T I2T 122.6(2) . . ?
F1T C3T C4T 118.2(3) . . ?
F1T C3T C2T 120.6(4) . . ?
C4T C3T C2T 121.2(3) . . ?
C5T C4T F2T 120.1(4) . . ?
C5T C4T C3T 120.3(3) . . ?
F2T C4T C3T 119.6(4) . . ?
F3T C5T C4T 120.3(3) . . ?
F3T C5T C6T 120.1(4) . . ?
C4T C5T C6T 119.6(3) . . ?
F4T C6T C1T 120.6(3) . . ?
F4T C6T C5T 117.6(3) . . ?
C1T C6T C5T 121.8(3) . . ?
N1A C1A C2A 110.9(6) . . ?
N1A C1A H1A1 109.5 . . ?
C2A C1A H1A1 109.5 . . ?
N1A C1A H1A2 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 108.1 . . ?
N2A C2A C1A 109.7(6) . . ?
N2A C2A H2A1 109.7 . . ?
C1A C2A H2A1 109.7 . . ?
N2A C2A H2A2 109.7 . . ?
C1A C2A H2A2 109.7 . . ?
H2A1 C2A H2A2 108.2 . . ?
N1A C3A C4A 110.8(6) . . ?
N1A C3A H3A1 109.5 . . ?
C4A C3A H3A1 109.5 . . ?
N1A C3A H3A2 109.5 . . ?
C4A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 108.1 . . ?
N2A C4A C3A 110.2(6) . . ?
N2A C4A H4A1 109.6 . . ?
C3A C4A H4A1 109.6 . . ?
N2A C4A H4A2 109.6 . . ?
C3A C4A H4A2 109.6 . . ?
H4A1 C4A H4A2 108.1 . . ?
N1A C5A C6A 111.1(6) . . ?
N1A C5A H5A1 109.4 . . ?
C6A C5A H5A1 109.4 . . ?
N1A C5A H5A2 109.4 . . ?
C6A C5A H5A2 109.4 . . ?
H5A1 C5A H5A2 108.0 . . ?
N2A C6A C5A 109.8(5) . . ?
N2A C6A H6A1 109.7 . . ?
C5A C6A H6A1 109.7 . . ?
N2A C6A H6A2 109.7 . . ?
C5A C6A H6A2 109.7 . . ?
H6A1 C6A H6A2 108.2 . . ?
C3A N1A C5A 108.9(7) . . ?
C3A N1A C1A 108.0(7) . . ?
C5A N1A C1A 108.1(6) . . ?
C4A N2A C6A 108.7(6) . . ?
C4A N2A C2A 108.9(7) . . ?
C6A N2A C2A 108.3(6) . . ?
N1A' C1A' C2A' 111.0(6) . . ?
N1A' C1A' H1A3 109.4 . . ?
C2A' C1A' H1A3 109.4 . . ?
N1A' C1A' H1A4 109.4 . . ?
C2A' C1A' H1A4 109.4 . . ?
H1A3 C1A' H1A4 108.0 . . ?
N2A' C2A' C1A' 109.8(6) . . ?
N2A' C2A' H2A3 109.7 . . ?
C1A' C2A' H2A3 109.7 . . ?
N2A' C2A' H2A4 109.7 . . ?
C1A' C2A' H2A4 109.7 . . ?
H2A3 C2A' H2A4 108.2 . . ?
N1A' C3A' C4A' 111.2(6) . . ?
N1A' C3A' H3A3 109.4 . . ?
C4A' C3A' H3A3 109.4 . . ?
N1A' C3A' H3A4 109.4 . . ?
C4A' C3A' H3A4 109.4 . . ?
H3A3 C3A' H3A4 108.0 . . ?
N2A' C4A' C3A' 109.9(6) . . ?
N2A' C4A' H4A3 109.7 . . ?
C3A' C4A' H4A3 109.7 . . ?
N2A' C4A' H4A4 109.7 . . ?
C3A' C4A' H4A4 109.7 . . ?
H4A3 C4A' H4A4 108.2 . . ?
N1A' C5A' C6A' 110.6(6) . . ?
N1A' C5A' H5A3 109.5 . . ?
C6A' C5A' H5A3 109.5 . . ?
N1A' C5A' H5A4 109.5 . . ?
C6A' C5A' H5A4 109.5 . . ?
H5A3 C5A' H5A4 108.1 . . ?
N2A' C6A' C5A' 110.4(6) . . ?
N2A' C6A' H6A3 109.6 . . ?
C5A' C6A' H6A3 109.6 . . ?
N2A' C6A' H6A4 109.6 . . ?
C5A' C6A' H6A4 109.6 . . ?
H6A3 C6A' H6A4 108.1 . . ?
C3A' N1A' C1A' 108.9(7) . . ?
C3A' N1A' C5A' 107.7(7) . . ?
C1A' N1A' C5A' 108.3(7) . . ?
C6A' N2A' C4A' 108.4(7) . . ?
C6A' N2A' C2A' 109.3(7) . . ?
C4A' N2A' C2A' 108.0(7) . . ?

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
C6S C1S C2S C3S -0.2(4) . . . . ?
I1S C1S C2S C3S 178.7(2) . . . . ?
C6S C1S C2S I2S 178.2(2) . . . . ?
I1S C1S C2S I2S -2.9(4) . . . . ?
C1S C2S C3S F1S 180.0(3) . . . . ?
I2S C2S C3S F1S 1.5(4) . . . . ?
C1S C2S C3S C4S -0.4(5) . . . . ?
I2S C2S C3S C4S -178.9(3) . . . . ?
F1S C3S C4S F2S 0.6(5) . . . . ?
C2S C3S C4S F2S -179.0(3) . . . . ?
F1S C3S C4S C5S -179.4(3) . . . . ?
C2S C3S C4S C5S 1.0(5) . . . . ?
F2S C4S C5S F3S -0.5(5) . . . . ?
C3S C4S C5S F3S 179.5(3) . . . . ?
F2S C4S C5S C6S 179.1(3) . . . . ?
C3S C4S C5S C6S -0.9(5) . . . . ?
F3S C5S C6S F4S -0.2(5) . . . . ?
C4S C5S C6S F4S -179.8(3) . . . . ?
F3S C5S C6S C1S 179.9(3) . . . . ?
C4S C5S C6S C1S 0.3(5) . . . . ?
C2S C1S C6S F4S -179.6(3) . . . . ?
I1S C1S C6S F4S 1.4(4) . . . . ?
C2S C1S C6S C5S 0.2(5) . . . . ?
I1S C1S C6S C5S -178.7(3) . . . . ?
C6T C1T C2T C3T -0.3(4) . . . . ?
I1T C1T C2T C3T 178.6(2) . . . . ?
C6T C1T C2T I2T -179.9(2) . . . . ?
I1T C1T C2T I2T -1.0(4) . . . . ?
C1T C2T C3T F1T 179.0(3) . . . . ?
I2T C2T C3T F1T -1.4(4) . . . . ?
C1T C2T C3T C4T 0.0(5) . . . . ?
I2T C2T C3T C4T 179.6(3) . . . . ?
F1T C3T C4T C5T -178.8(3) . . . . ?
C2T C3T C4T C5T 0.3(5) . . . . ?
F1T C3T C4T F2T 1.2(5) . . . . ?
C2T C3T C4T F2T -179.7(3) . . . . ?
F2T C4T C5T F3T -0.9(5) . . . . ?
C3T C4T C5T F3T 179.0(3) . . . . ?
F2T C4T C5T C6T 179.8(3) . . . . ?
C3T C4T C5T C6T -0.2(6) . . . . ?
C2T C1T C6T F4T 179.8(3) . . . . ?
I1T C1T C6T F4T 0.9(4) . . . . ?
C2T C1T C6T C5T 0.4(5) . . . . ?
I1T C1T C6T C5T -178.6(3) . . . . ?
F3T C5T C6T F4T 1.2(5) . . . . ?
C4T C5T C6T F4T -179.6(3) . . . . ?
F3T C5T C6T C1T -179.4(3) . . . . ?
C4T C5T C6T C1T -0.1(5) . . . . ?
N1A C1A C2A N2A -3.2(12) . . . . ?
N1A C3A C4A N2A -1.9(12) . . . . ?
N1A C5A C6A N2A -2.8(11) . . . . ?
C4A C3A N1A C5A 59.3(10) . . . . ?
C4A C3A N1A C1A -57.8(10) . . . . ?
C6A C5A N1A C3A -56.6(10) . . . . ?
C6A C5A N1A C1A 60.5(10) . . . . ?
C2A C1A N1A C3A 60.8(10) . . . . ?
C2A C1A N1A C5A -56.9(10) . . . . ?
C3A C4A N2A C6A -57.8(10) . . . . ?
C3A C4A N2A C2A 60.0(10) . . . . ?
C5A C6A N2A C4A 60.4(9) . . . . ?
C5A C6A N2A C2A -57.8(9) . . . . ?
C1A C2A N2A C4A -56.9(10) . . . . ?
C1A C2A N2A C6A 61.2(9) . . . . ?
N1A' C1A' C2A' N2A' 2.7(13) . . . . ?
N1A' C3A' C4A' N2A' 0.0(12) . . . . ?
N1A' C5A' C6A' N2A' 1.1(13) . . . . ?
C4A' C3A' N1A' C1A' -58.1(10) . . . . ?
C4A' C3A' N1A' C5A' 59.0(10) . . . . ?
C2A' C1A' N1A' C3A' 56.5(11) . . . . ?
C2A' C1A' N1A' C5A' -60.3(11) . . . . ?
C6A' C5A' N1A' C3A' -59.6(11) . . . . ?
C6A' C5A' N1A' C1A' 58.0(11) . . . . ?
C5A' C6A' N2A' C4A' 58.3(11) . . . . ?
C5A' C6A' N2A' C2A' -59.2(11) . . . . ?
C3A' C4A' N2A' C6A' -58.9(10) . . . . ?
C3A' C4A' N2A' C2A' 59.4(10) . . . . ?
C1A' C2A' N2A' C6A' 56.8(11) . . . . ?
C1A' C2A' N2A' C4A' -60.9(11) . . . . ?

_refine_diff_density_max         1.455
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.119


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

data_dabco_12tfib_2-1_253K
_database_code_depnum_ccdc_archive 'CCDC 1990462'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2020-03-15 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C6 F4 I2, 2(C6 H12 N2)'
_chemical_formula_sum            'C18 H24 F4 I2 N4'
_chemical_formula_weight         626.21

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                   6.5273(5)
_cell_length_b                   17.4784(13)
_cell_length_c                   19.2084(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2191.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    253.0(1)
_cell_measurement_reflns_used    9024
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      31.05

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.830
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    2.914
_shelx_estimated_absorpt_T_min   0.196
_shelx_estimated_absorpt_T_max   0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3530
_exptl_absorpt_correction_T_max  0.9140
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'

_diffrn_ambient_temperature      253.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Mo)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 CMOS
_diffrn_detector_type            'PHOTON 100'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            38549
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.152
_diffrn_reflns_theta_max         33.197
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8233
_reflns_number_gt                6605
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.999

_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 APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_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)+(0.0200P)²+3.2121P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.0043(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2316 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(12)
_chemical_absolute_configuration .
_refine_ls_number_reflns         8233
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
C1S C 0.5029(8) 0.3368(3) 0.2145(3) 0.0287(10) Uani 1 1 d . . . . .
C2S C 0.4500(7) 0.4103(3) 0.2358(3) 0.0274(10) Uani 1 1 d . . . . .
C3S C 0.2788(9) 0.4438(3) 0.2071(3) 0.0349(12) Uani 1 1 d . . . . .
C4S C 0.1586(9) 0.4071(4) 0.1582(3) 0.0385(13) Uani 1 1 d . . . . .
C5S C 0.2094(9) 0.3354(4) 0.1371(3) 0.0382(13) Uani 1 1 d . . . . .
C6S C 0.3824(10) 0.3011(3) 0.1654(3) 0.0367(12) Uani 1 1 d . . . . .
F1S F 0.2228(6) 0.5156(2) 0.2258(2) 0.0551(10) Uani 1 1 d . . . . .
F2S F -0.0086(6) 0.4416(3) 0.1317(2) 0.0627(12) Uani 1 1 d . . . . .
F3S F 0.0958(7) 0.2987(3) 0.0902(2) 0.0616(12) Uani 1 1 d . . . . .
F4S F 0.4290(7) 0.2305(2) 0.1420(2) 0.0550(10) Uani 1 1 d . . . . .
I1S I 0.75008(6) 0.27540(2) 0.25839(2) 0.03769(10) Uani 1 1 d . . . . .
I2S I 0.62331(6) 0.47330(2) 0.30989(2) 0.03563(10) Uani 1 1 d . . . . .
C1A C 0.9454(9) 0.1591(4) 0.3935(3) 0.0410(14) Uani 1 1 d . . . . .
H1A1 H 0.866272 0.118318 0.372252 0.049 Uiso 1 1 calc R U . . .
H1A2 H 0.851625 0.192576 0.418107 0.049 Uiso 1 1 calc R U . . .
C2A C 1.1017(11) 0.1249(5) 0.4451(3) 0.0488(16) Uani 1 1 d . . . . .
H2A1 H 1.073100 0.143839 0.491548 0.059 Uiso 1 1 calc R U . . .
H2A2 H 1.087666 0.069661 0.445764 0.059 Uiso 1 1 calc R U . . .
C3A C 1.1938(8) 0.1502(4) 0.3033(3) 0.0380(13) Uani 1 1 d . . . . .
H3A1 H 1.266112 0.177724 0.267054 0.046 Uiso 1 1 calc R U . . .
H3A2 H 1.116245 0.109263 0.281606 0.046 Uiso 1 1 calc R U . . .
C4A C 1.3482(10) 0.1162(4) 0.3547(3) 0.0449(15) Uani 1 1 d . . . . .
H4A1 H 1.336927 0.060848 0.354380 0.054 Uiso 1 1 calc R U . . .
H4A2 H 1.486004 0.129620 0.340273 0.054 Uiso 1 1 calc R U . . .
C5A C 1.1740(12) 0.2629(4) 0.3724(4) 0.0547(18) Uani 1 1 d . . . . .
H5A1 H 1.083655 0.297694 0.397049 0.066 Uiso 1 1 calc R U . . .
H5A2 H 1.246416 0.291853 0.337029 0.066 Uiso 1 1 calc R U . . .
C6A C 1.3298(11) 0.2277(5) 0.4240(4) 0.0595(19) Uani 1 1 d . . . . .
H6A1 H 1.467722 0.241524 0.410093 0.071 Uiso 1 1 calc R U . . .
H6A2 H 1.305867 0.248176 0.470255 0.071 Uiso 1 1 calc R U . . .
N1A N 1.0531(7) 0.2024(3) 0.3394(2) 0.0330(10) Uani 1 1 d . . . . .
N2A N 1.3110(8) 0.1450(4) 0.4258(3) 0.0470(14) Uani 1 1 d . . . . .
C1B C 1.0084(11) 0.4779(4) 0.4326(4) 0.0514(16) Uani 1 1 d . . . . .
H1B1 H 1.087310 0.456679 0.394394 0.062 Uiso 1 1 calc R U . . .
H1B2 H 0.919589 0.438002 0.450589 0.062 Uiso 1 1 calc R U . . .
C2B C 1.1538(12) 0.5056(4) 0.4903(4) 0.057(2) Uani 1 1 d . . . . .
H2B1 H 1.124626 0.477990 0.533025 0.068 Uiso 1 1 calc R U . . .
H2B2 H 1.294205 0.494612 0.477106 0.068 Uiso 1 1 calc R U . . .
C3B C 1.0225(10) 0.6011(4) 0.3797(3) 0.0399(13) Uani 1 1 d . . . . .
H3B1 H 0.943647 0.644653 0.363436 0.048 Uiso 1 1 calc R U . . .
H3B2 H 1.098217 0.580492 0.340558 0.048 Uiso 1 1 calc R U . . .
C4B C 1.1726(10) 0.6271(4) 0.4366(3) 0.0493(17) Uani 1 1 d . . . . .
H4B1 H 1.311927 0.616566 0.421872 0.059 Uiso 1 1 calc R U . . .
H4B2 H 1.159579 0.681835 0.443654 0.059 Uiso 1 1 calc R U . . .
C5B C 0.7708(10) 0.5759(4) 0.4655(3) 0.0443(14) Uani 1 1 d . . . . .
H5B1 H 0.677494 0.538157 0.484645 0.053 Uiso 1 1 calc R U . . .
H5B2 H 0.690592 0.619015 0.449218 0.053 Uiso 1 1 calc R U . . .
C6B C 0.9208(11) 0.6028(6) 0.5227(4) 0.059(2) Uani 1 1 d . . . . .
H6B1 H 0.903730 0.657226 0.530414 0.071 Uiso 1 1 calc R U . . .
H6B2 H 0.890150 0.576470 0.565947 0.071 Uiso 1 1 calc R U . . .
N1B N 0.8838(8) 0.5426(3) 0.4075(2) 0.0343(9) Uani 1 1 d . . . . .
N2B N 1.1313(9) 0.5871(4) 0.5025(3) 0.0464(13) 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
C1S C6S 1.377(8) . ?
C1S C2S 1.392(7) . ?
C1S I1S 2.113(5) . ?
C2S C3S 1.377(7) . ?
C2S I2S 2.126(5) . ?
C3S F1S 1.355(7) . ?
C3S C4S 1.382(8) . ?
C4S F2S 1.346(7) . ?
C4S C5S 1.359(9) . ?
C5S F3S 1.332(6) . ?
C5S C6S 1.389(9) . ?
C6S F4S 1.349(7) . ?
C1A N1A 1.464(8) . ?
C1A C2A 1.543(9) . ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
C2A N2A 1.459(9) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A N1A 1.468(7) . ?
C3A C4A 1.530(8) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A N2A 1.476(8) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A N1A 1.464(8) . ?
C5A C6A 1.548(11) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6A N2A 1.450(11) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C1B N1B 1.475(8) . ?
C1B C2B 1.538(10) . ?
C1B H1B1 0.9700 . ?
C1B H1B2 0.9700 . ?
C2B N2B 1.451(10) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C3B N1B 1.467(8) . ?
C3B C4B 1.537(9) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C4B N2B 1.470(8) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5B N1B 1.458(8) . ?
C5B C6B 1.544(9) . ?
C5B H5B1 0.9700 . ?
C5B H5B2 0.9700 . ?
C6B N2B 1.454(10) . ?
C6B H6B1 0.9700 . ?
C6B H6B2 0.9700 . ?

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
C6S C1S C2S 118.5(5) . . ?
C6S C1S I1S 118.7(4) . . ?
C2S C1S I1S 122.7(4) . . ?
C3S C2S C1S 118.5(5) . . ?
C3S C2S I2S 118.6(4) . . ?
C1S C2S I2S 122.9(4) . . ?
F1S C3S C2S 120.4(5) . . ?
F1S C3S C4S 117.2(5) . . ?
C2S C3S C4S 122.4(5) . . ?
F2S C4S C5S 119.8(6) . . ?
F2S C4S C3S 120.6(6) . . ?
C5S C4S C3S 119.5(5) . . ?
F3S C5S C4S 120.7(6) . . ?
F3S C5S C6S 120.6(6) . . ?
C4S C5S C6S 118.7(5) . . ?
F4S C6S C1S 120.9(6) . . ?
F4S C6S C5S 116.6(5) . . ?
C1S C6S C5S 122.5(6) . . ?
N1A C1A C2A 109.7(5) . . ?
N1A C1A H1A1 109.7 . . ?
C2A C1A H1A1 109.7 . . ?
N1A C1A H1A2 109.7 . . ?
C2A C1A H1A2 109.7 . . ?
H1A1 C1A H1A2 108.2 . . ?
N2A C2A C1A 111.2(5) . . ?
N2A C2A H2A1 109.4 . . ?
C1A C2A H2A1 109.4 . . ?
N2A C2A H2A2 109.4 . . ?
C1A C2A H2A2 109.4 . . ?
H2A1 C2A H2A2 108.0 . . ?
N1A C3A C4A 110.4(5) . . ?
N1A C3A H3A1 109.6 . . ?
C4A C3A H3A1 109.6 . . ?
N1A C3A H3A2 109.6 . . ?
C4A C3A H3A2 109.6 . . ?
H3A1 C3A H3A2 108.1 . . ?
N2A C4A C3A 110.8(5) . . ?
N2A C4A H4A1 109.5 . . ?
C3A C4A H4A1 109.5 . . ?
N2A C4A H4A2 109.5 . . ?
C3A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 108.1 . . ?
N1A C5A C6A 110.1(6) . . ?
N1A C5A H5A1 109.6 . . ?
C6A C5A H5A1 109.6 . . ?
N1A C5A H5A2 109.6 . . ?
C6A C5A H5A2 109.6 . . ?
H5A1 C5A H5A2 108.2 . . ?
N2A C6A C5A 110.8(5) . . ?
N2A C6A H6A1 109.5 . . ?
C5A C6A H6A1 109.5 . . ?
N2A C6A H6A2 109.5 . . ?
C5A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 108.1 . . ?
C1A N1A C5A 109.0(5) . . ?
C1A N1A C3A 108.3(5) . . ?
C5A N1A C3A 108.5(5) . . ?
C6A N2A C2A 109.0(6) . . ?
C6A N2A C4A 107.8(6) . . ?
C2A N2A C4A 107.9(6) . . ?
N1B C1B C2B 109.6(6) . . ?
N1B C1B H1B1 109.8 . . ?
C2B C1B H1B1 109.8 . . ?
N1B C1B H1B2 109.8 . . ?
C2B C1B H1B2 109.8 . . ?
H1B1 C1B H1B2 108.2 . . ?
N2B C2B C1B 111.3(5) . . ?
N2B C2B H2B1 109.4 . . ?
C1B C2B H2B1 109.4 . . ?
N2B C2B H2B2 109.4 . . ?
C1B C2B H2B2 109.4 . . ?
H2B1 C2B H2B2 108.0 . . ?
N1B C3B C4B 110.0(5) . . ?
N1B C3B H3B1 109.7 . . ?
C4B C3B H3B1 109.7 . . ?
N1B C3B H3B2 109.7 . . ?
C4B C3B H3B2 109.7 . . ?
H3B1 C3B H3B2 108.2 . . ?
N2B C4B C3B 110.8(5) . . ?
N2B C4B H4B1 109.5 . . ?
C3B C4B H4B1 109.5 . . ?
N2B C4B H4B2 109.5 . . ?
C3B C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 108.1 . . ?
N1B C5B C6B 110.2(5) . . ?
N1B C5B H5B1 109.6 . . ?
C6B C5B H5B1 109.6 . . ?
N1B C5B H5B2 109.6 . . ?
C6B C5B H5B2 109.6 . . ?
H5B1 C5B H5B2 108.1 . . ?
N2B C6B C5B 110.6(5) . . ?
N2B C6B H6B1 109.5 . . ?
C5B C6B H6B1 109.5 . . ?
N2B C6B H6B2 109.5 . . ?
C5B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 108.1 . . ?
C5B N1B C3B 108.1(5) . . ?
C5B N1B C1B 109.5(5) . . ?
C3B N1B C1B 108.3(5) . . ?
C2B N2B C6B 108.9(6) . . ?
C2B N2B C4B 108.0(6) . . ?
C6B N2B C4B 108.3(6) . . ?

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
C6S C1S C2S C3S 0.4(7) . . . . ?
I1S C1S C2S C3S -176.0(4) . . . . ?
C6S C1S C2S I2S -179.1(4) . . . . ?
I1S C1S C2S I2S 4.5(6) . . . . ?
C1S C2S C3S F1S -179.3(5) . . . . ?
I2S C2S C3S F1S 0.2(7) . . . . ?
C1S C2S C3S C4S -0.1(8) . . . . ?
I2S C2S C3S C4S 179.4(4) . . . . ?
F1S C3S C4S F2S -1.2(8) . . . . ?
C2S C3S C4S F2S 179.5(5) . . . . ?
F1S C3S C4S C5S 179.3(5) . . . . ?
C2S C3S C4S C5S 0.0(9) . . . . ?
F2S C4S C5S F3S 0.2(8) . . . . ?
C3S C4S C5S F3S 179.7(5) . . . . ?
F2S C4S C5S C6S -179.8(5) . . . . ?
C3S C4S C5S C6S -0.3(8) . . . . ?
C2S C1S C6S F4S 178.8(5) . . . . ?
I1S C1S C6S F4S -4.7(7) . . . . ?
C2S C1S C6S C5S -0.7(8) . . . . ?
I1S C1S C6S C5S 175.9(4) . . . . ?
F3S C5S C6S F4S 1.1(8) . . . . ?
C4S C5S C6S F4S -178.9(5) . . . . ?
F3S C5S C6S C1S -179.4(5) . . . . ?
C4S C5S C6S C1S 0.6(8) . . . . ?
N1A C1A C2A N2A 0.0(8) . . . . ?
N1A C3A C4A N2A 0.4(8) . . . . ?
N1A C5A C6A N2A -0.6(8) . . . . ?
C2A C1A N1A C5A -58.6(7) . . . . ?
C2A C1A N1A C3A 59.3(7) . . . . ?
C6A C5A N1A C1A 59.1(7) . . . . ?
C6A C5A N1A C3A -58.6(7) . . . . ?
C4A C3A N1A C1A -59.6(6) . . . . ?
C4A C3A N1A C5A 58.6(7) . . . . ?
C5A C6A N2A C2A -57.7(7) . . . . ?
C5A C6A N2A C4A 59.1(7) . . . . ?
C1A C2A N2A C6A 58.3(8) . . . . ?
C1A C2A N2A C4A -58.4(8) . . . . ?
C3A C4A N2A C6A -59.3(7) . . . . ?
C3A C4A N2A C2A 58.2(8) . . . . ?
N1B C1B C2B N2B -1.4(8) . . . . ?
N1B C3B C4B N2B -1.2(8) . . . . ?
N1B C5B C6B N2B -0.2(9) . . . . ?
C6B C5B N1B C3B -59.5(7) . . . . ?
C6B C5B N1B C1B 58.3(7) . . . . ?
C4B C3B N1B C5B 60.0(7) . . . . ?
C4B C3B N1B C1B -58.6(7) . . . . ?
C2B C1B N1B C5B -57.5(7) . . . . ?
C2B C1B N1B C3B 60.3(7) . . . . ?
C1B C2B N2B C6B 59.4(7) . . . . ?
C1B C2B N2B C4B -58.0(8) . . . . ?
C5B C6B N2B C2B -58.5(8) . . . . ?
C5B C6B N2B C4B 58.7(8) . . . . ?
C3B C4B N2B C2B 59.6(7) . . . . ?
C3B C4B N2B C6B -58.2(8) . . . . ?

_refine_diff_density_max         1.243
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.122


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_dabco_12tfib_1-1_LT_173K
_database_code_depnum_ccdc_archive 'CCDC 1990463'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2020-03-15 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C6 H12 N2, C6 F4 I2'
_chemical_formula_sum            'C12 H12 F4 I2 N2'
_chemical_formula_weight         514.04

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'
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'
N N 0.0311 0.0180 '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                   6.7231(5)
_cell_length_b                   14.0970(10)
_cell_length_c                   17.5147(13)
_cell_angle_alpha                76.882(3)
_cell_angle_beta                 80.884(3)
_cell_angle_gamma                78.615(2)
_cell_volume                     1573.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.0(1)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      5.22
_cell_measurement_theta_max      74.60

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.170
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    31.730
_shelx_estimated_absorpt_T_min   0.036
_shelx_estimated_absorpt_T_max   0.147
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0040
_exptl_absorpt_correction_T_max  0.1313
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Cu)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            20462
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.609
_diffrn_reflns_theta_max         74.641
_diffrn_reflns_theta_full        67.750
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6297
_reflns_number_gt                5488
_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 APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_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)+(0.1255P)²+5.5458P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.00130(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6297
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1899
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_PLAT971_dabco1_12tfib1_173K 
;
PROBLEM: Check Calcd Resid. Dens.  0.87A   From I1T             2.64 eA-3  
PROBLEM: Check Calcd Resid. Dens.  1.05A   From I2S             2.61 eA-3  
PROBLEM: Check Calcd Resid. Dens.  0.68A   From I2T             2.54 eA-3  
RESPONSE: The crystal in question has gone through a phase transition.
;
# end Validation Reply Form

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
C1A C 0.6255(12) 0.6718(6) 0.0690(5) 0.0383(17) Uani 1 1 d . . . . .
H1A1 H 0.569297 0.680416 0.123193 0.046 Uiso 1 1 calc R U . . .
H1A2 H 0.629678 0.601961 0.066457 0.046 Uiso 1 1 calc R U . . .
C2A C 0.4856(11) 0.7399(6) 0.0095(4) 0.0346(15) Uani 1 1 d . . . . .
H2A1 H 0.433343 0.699632 -0.019952 0.042 Uiso 1 1 calc R U . . .
H2A2 H 0.367179 0.776457 0.038148 0.042 Uiso 1 1 calc R U . . .
C3A C 0.8260(13) 0.7969(6) 0.0567(5) 0.0393(17) Uani 1 1 d . . . . .
H3A1 H 0.965276 0.813579 0.042879 0.047 Uiso 1 1 calc R U . . .
H3A2 H 0.777333 0.805044 0.111562 0.047 Uiso 1 1 calc R U . . .
C4A C 0.6811(14) 0.8675(6) -0.0002(5) 0.0415(18) Uani 1 1 d . . . . .
H4A1 H 0.565852 0.903214 0.030500 0.050 Uiso 1 1 calc R U . . .
H4A2 H 0.756202 0.916887 -0.036537 0.050 Uiso 1 1 calc R U . . .
C5A C 0.9134(12) 0.6840(6) -0.0299(4) 0.0366(16) Uani 1 1 d . . . . .
H5A1 H 0.918461 0.614946 -0.034910 0.044 Uiso 1 1 calc R U . . .
H5A2 H 1.054173 0.698942 -0.042114 0.044 Uiso 1 1 calc R U . . .
C6A C 0.7755(13) 0.7552(6) -0.0887(4) 0.0377(17) Uani 1 1 d . . . . .
H6A1 H 0.856101 0.801908 -0.125441 0.045 Uiso 1 1 calc R U . . .
H6A2 H 0.724545 0.716908 -0.120236 0.045 Uiso 1 1 calc R U . . .
N1A N 0.8319(10) 0.6951(5) 0.0511(4) 0.0321(13) Uani 1 1 d . . . . .
N2A N 0.6019(10) 0.8104(5) -0.0462(4) 0.0345(13) Uani 1 1 d . . . . .
C1B C 0.6770(14) 0.6824(6) 0.4523(5) 0.0405(18) Uani 1 1 d . . . . .
H1B1 H 0.694126 0.609460 0.467786 0.049 Uiso 1 1 calc R U . . .
H1B2 H 0.638085 0.702142 0.397991 0.049 Uiso 1 1 calc R U . . .
C2B C 0.5058(12) 0.7292(6) 0.5096(5) 0.0390(17) Uani 1 1 d . . . . .
H2B1 H 0.395839 0.770948 0.479590 0.047 Uiso 1 1 calc R U . . .
H2B2 H 0.446196 0.676339 0.548503 0.047 Uiso 1 1 calc R U . . .
C3B C 0.9266(13) 0.6831(6) 0.5352(5) 0.0384(17) Uani 1 1 d . . . . .
H3B1 H 1.055292 0.705837 0.537621 0.046 Uiso 1 1 calc R U . . .
H3B2 H 0.949456 0.610058 0.550275 0.046 Uiso 1 1 calc R U . . .
C4B C 0.7539(14) 0.7271(6) 0.5935(4) 0.0377(17) Uani 1 1 d . . . . .
H4B1 H 0.699955 0.672862 0.632743 0.045 Uiso 1 1 calc R U . . .
H4B2 H 0.809494 0.767021 0.622193 0.045 Uiso 1 1 calc R U . . .
C5B C 0.8397(14) 0.8232(6) 0.4333(5) 0.0423(18) Uani 1 1 d . . . . .
H5B1 H 0.801473 0.846037 0.379020 0.051 Uiso 1 1 calc R U . . .
H5B2 H 0.968981 0.845947 0.434793 0.051 Uiso 1 1 calc R U . . .
C6B C 0.6689(14) 0.8681(5) 0.4922(5) 0.0411(18) Uani 1 1 d . . . . .
H6B1 H 0.725014 0.910027 0.518857 0.049 Uiso 1 1 calc R U . . .
H6B2 H 0.557426 0.910036 0.463099 0.049 Uiso 1 1 calc R U . . .
N1B N 0.8698(10) 0.7147(5) 0.4540(4) 0.0338(13) Uani 1 1 d . . . . .
N2B N 0.5885(11) 0.7892(5) 0.5508(4) 0.0349(14) Uani 1 1 d . . . . .
C1S C 1.3567(11) 0.5096(5) 0.2174(4) 0.0270(13) Uani 1 1 d . . . . .
C2S C 1.3858(11) 0.5296(5) 0.2884(4) 0.0280(14) Uani 1 1 d . . . . .
C3S C 1.5670(12) 0.4860(5) 0.3204(4) 0.0321(15) Uani 1 1 d . . . . .
C4S C 1.7148(13) 0.4227(5) 0.2837(5) 0.0345(16) Uani 1 1 d . . . . .
C5S C 1.6818(14) 0.4006(5) 0.2143(4) 0.0358(17) Uani 1 1 d . . . . .
C6S C 1.5064(13) 0.4443(5) 0.1823(4) 0.0333(15) Uani 1 1 d . . . . .
F1S F 1.6027(9) 0.5019(4) 0.3892(3) 0.0457(12) Uani 1 1 d . . . . .
F2S F 1.8893(8) 0.3826(4) 0.3153(3) 0.0490(13) Uani 1 1 d . . . . .
F3S F 1.8263(9) 0.3394(4) 0.1787(3) 0.0498(13) Uani 1 1 d . . . . .
F4S F 1.4863(9) 0.4242(4) 0.1119(3) 0.0459(12) Uani 1 1 d . . . . .
I1S I 1.11006(7) 0.58274(3) 0.15190(3) 0.03300(19) Uani 1 1 d . . . . .
I2S I 1.16633(8) 0.61817(3) 0.35521(3) 0.0354(2) Uani 1 1 d . . . . .
C1T C 0.0457(12) 0.9635(5) 0.7151(4) 0.0299(14) Uani 1 1 d . . . . .
C2T C 0.0632(11) 0.9827(5) 0.7881(4) 0.0275(13) Uani 1 1 d . . . . .
C3T C -0.0914(13) 1.0480(6) 0.8202(5) 0.0330(15) Uani 1 1 d . . . . .
C4T C -0.2611(14) 1.0917(6) 0.7848(5) 0.0395(18) Uani 1 1 d . . . . .
C5T C -0.2844(13) 1.0692(6) 0.7135(5) 0.0393(17) Uani 1 1 d . . . . .
C6T C -0.1293(12) 1.0063(6) 0.6803(4) 0.0324(15) Uani 1 1 d . . . . .
F1T F -0.0812(9) 1.0686(4) 0.8910(3) 0.0447(11) Uani 1 1 d . . . . .
F2T F -0.4086(9) 1.1552(4) 0.8167(4) 0.0556(14) Uani 1 1 d . . . . .
F3T F -0.4492(9) 1.1118(5) 0.6773(3) 0.0554(14) Uani 1 1 d . . . . .
F4T F -0.1535(9) 0.9903(4) 0.6097(3) 0.0502(13) Uani 1 1 d . . . . .
I1T I 0.27916(8) 0.87864(3) 0.64998(3) 0.0348(2) Uani 1 1 d . . . . .
I2T I 0.30953(7) 0.91534(3) 0.85511(3) 0.0341(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A N1A 1.458(10) . ?
C1A C2A 1.547(10) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C2A N2A 1.474(9) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A N1A 1.452(10) . ?
C3A C4A 1.552(11) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A N2A 1.477(11) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A N1A 1.469(10) . ?
C5A C6A 1.548(10) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A N2A 1.467(11) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C1B N1B 1.463(11) . ?
C1B C2B 1.550(12) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C2B N2B 1.462(10) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B N1B 1.478(10) . ?
C3B C4B 1.550(11) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C4B N2B 1.464(10) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C5B N1B 1.470(9) . ?
C5B C6B 1.554(12) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B N2B 1.459(10) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C1S C2S 1.385(10) . ?
C1S C6S 1.391(10) . ?
C1S I1S 2.126(7) . ?
C2S C3S 1.393(10) . ?
C2S I2S 2.121(7) . ?
C3S F1S 1.341(9) . ?
C3S C4S 1.380(11) . ?
C4S F2S 1.344(9) . ?
C4S C5S 1.381(11) . ?
C5S F3S 1.340(9) . ?
C5S C6S 1.361(12) . ?
C6S F4S 1.357(9) . ?
C1T C6T 1.378(11) . ?
C1T C2T 1.394(10) . ?
C1T I1T 2.122(7) . ?
C2T C3T 1.384(11) . ?
C2T I2T 2.124(7) . ?
C3T F1T 1.351(9) . ?
C3T C4T 1.356(12) . ?
C4T F2T 1.341(10) . ?
C4T C5T 1.395(12) . ?
C5T F3T 1.333(9) . ?
C5T C6T 1.374(11) . ?
C6T F4T 1.346(9) . ?

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
N1A C1A C2A 110.5(6) . . ?
N1A C1A H1A1 109.6 . . ?
C2A C1A H1A1 109.6 . . ?
N1A C1A H1A2 109.6 . . ?
C2A C1A H1A2 109.6 . . ?
H1A1 C1A H1A2 108.1 . . ?
N2A C2A C1A 109.6(6) . . ?
N2A C2A H2A1 109.7 . . ?
C1A C2A H2A1 109.7 . . ?
N2A C2A H2A2 109.7 . . ?
C1A C2A H2A2 109.7 . . ?
H2A1 C2A H2A2 108.2 . . ?
N1A C3A C4A 110.1(6) . . ?
N1A C3A H3A1 109.6 . . ?
C4A C3A H3A1 109.6 . . ?
N1A C3A H3A2 109.6 . . ?
C4A C3A H3A2 109.6 . . ?
H3A1 C3A H3A2 108.2 . . ?
N2A C4A C3A 109.8(6) . . ?
N2A C4A H4A1 109.7 . . ?
C3A C4A H4A1 109.7 . . ?
N2A C4A H4A2 109.7 . . ?
C3A C4A H4A2 109.7 . . ?
H4A1 C4A H4A2 108.2 . . ?
N1A C5A C6A 109.7(6) . . ?
N1A C5A H5A1 109.7 . . ?
C6A C5A H5A1 109.7 . . ?
N1A C5A H5A2 109.7 . . ?
C6A C5A H5A2 109.7 . . ?
H5A1 C5A H5A2 108.2 . . ?
N2A C6A C5A 110.4(6) . . ?
N2A C6A H6A1 109.6 . . ?
C5A C6A H6A1 109.6 . . ?
N2A C6A H6A2 109.6 . . ?
C5A C6A H6A2 109.6 . . ?
H6A1 C6A H6A2 108.1 . . ?
C3A N1A C1A 109.4(6) . . ?
C3A N1A C5A 108.5(6) . . ?
C1A N1A C5A 109.4(6) . . ?
C6A N2A C2A 109.1(6) . . ?
C6A N2A C4A 108.7(7) . . ?
C2A N2A C4A 108.2(6) . . ?
N1B C1B C2B 110.3(6) . . ?
N1B C1B H1B1 109.6 . . ?
C2B C1B H1B1 109.6 . . ?
N1B C1B H1B2 109.6 . . ?
C2B C1B H1B2 109.6 . . ?
H1B1 C1B H1B2 108.1 . . ?
N2B C2B C1B 110.1(6) . . ?
N2B C2B H2B1 109.6 . . ?
C1B C2B H2B1 109.6 . . ?
N2B C2B H2B2 109.6 . . ?
C1B C2B H2B2 109.6 . . ?
H2B1 C2B H2B2 108.1 . . ?
N1B C3B C4B 109.9(6) . . ?
N1B C3B H3B1 109.7 . . ?
C4B C3B H3B1 109.7 . . ?
N1B C3B H3B2 109.7 . . ?
C4B C3B H3B2 109.7 . . ?
H3B1 C3B H3B2 108.2 . . ?
N2B C4B C3B 110.3(6) . . ?
N2B C4B H4B1 109.6 . . ?
C3B C4B H4B1 109.6 . . ?
N2B C4B H4B2 109.6 . . ?
C3B C4B H4B2 109.6 . . ?
H4B1 C4B H4B2 108.1 . . ?
N1B C5B C6B 110.3(6) . . ?
N1B C5B H5B1 109.6 . . ?
C6B C5B H5B1 109.6 . . ?
N1B C5B H5B2 109.6 . . ?
C6B C5B H5B2 109.6 . . ?
H5B1 C5B H5B2 108.1 . . ?
N2B C6B C5B 109.9(6) . . ?
N2B C6B H6B1 109.7 . . ?
C5B C6B H6B1 109.7 . . ?
N2B C6B H6B2 109.7 . . ?
C5B C6B H6B2 109.7 . . ?
H6B1 C6B H6B2 108.2 . . ?
C1B N1B C5B 108.8(6) . . ?
C1B N1B C3B 108.7(7) . . ?
C5B N1B C3B 108.2(6) . . ?
C6B N2B C2B 108.3(6) . . ?
C6B N2B C4B 109.5(7) . . ?
C2B N2B C4B 109.1(6) . . ?
C2S C1S C6S 118.8(6) . . ?
C2S C1S I1S 124.2(5) . . ?
C6S C1S I1S 116.7(5) . . ?
C1S C2S C3S 118.7(6) . . ?
C1S C2S I2S 124.3(5) . . ?
C3S C2S I2S 117.0(5) . . ?
F1S C3S C4S 117.2(7) . . ?
F1S C3S C2S 121.3(7) . . ?
C4S C3S C2S 121.5(7) . . ?
F2S C4S C3S 120.3(7) . . ?
F2S C4S C5S 120.2(7) . . ?
C3S C4S C5S 119.6(7) . . ?
F3S C5S C6S 121.7(7) . . ?
F3S C5S C4S 119.3(7) . . ?
C6S C5S C4S 119.0(7) . . ?
F4S C6S C5S 116.7(7) . . ?
F4S C6S C1S 120.8(7) . . ?
C5S C6S C1S 122.5(7) . . ?
C6T C1T C2T 118.4(7) . . ?
C6T C1T I1T 117.3(5) . . ?
C2T C1T I1T 124.2(5) . . ?
C3T C2T C1T 118.3(7) . . ?
C3T C2T I2T 117.6(5) . . ?
C1T C2T I2T 124.1(5) . . ?
F1T C3T C4T 116.7(7) . . ?
F1T C3T C2T 120.3(7) . . ?
C4T C3T C2T 122.9(7) . . ?
F2T C4T C3T 122.0(8) . . ?
F2T C4T C5T 118.9(8) . . ?
C3T C4T C5T 119.1(8) . . ?
F3T C5T C6T 121.5(8) . . ?
F3T C5T C4T 120.2(8) . . ?
C6T C5T C4T 118.2(7) . . ?
F4T C6T C5T 116.3(7) . . ?
F4T C6T C1T 120.7(7) . . ?
C5T C6T C1T 122.9(7) . . ?

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
N1A C1A C2A N2A -1.8(10) . . . . ?
N1A C3A C4A N2A -3.2(10) . . . . ?
N1A C5A C6A N2A -1.6(9) . . . . ?
C4A C3A N1A C1A -57.5(9) . . . . ?
C4A C3A N1A C5A 61.9(8) . . . . ?
C2A C1A N1A C3A 60.6(8) . . . . ?
C2A C1A N1A C5A -58.2(8) . . . . ?
C6A C5A N1A C3A -59.3(8) . . . . ?
C6A C5A N1A C1A 60.0(8) . . . . ?
C5A C6A N2A C2A -58.0(8) . . . . ?
C5A C6A N2A C4A 59.7(8) . . . . ?
C1A C2A N2A C6A 59.9(8) . . . . ?
C1A C2A N2A C4A -58.2(8) . . . . ?
C3A C4A N2A C6A -57.2(8) . . . . ?
C3A C4A N2A C2A 61.2(8) . . . . ?
N1B C1B C2B N2B -2.0(9) . . . . ?
N1B C3B C4B N2B -1.7(9) . . . . ?
N1B C5B C6B N2B 0.0(10) . . . . ?
C2B C1B N1B C5B -57.5(8) . . . . ?
C2B C1B N1B C3B 60.1(8) . . . . ?
C6B C5B N1B C1B 58.7(9) . . . . ?
C6B C5B N1B C3B -59.3(9) . . . . ?
C4B C3B N1B C1B -58.0(8) . . . . ?
C4B C3B N1B C5B 60.1(9) . . . . ?
C5B C6B N2B C2B -59.7(9) . . . . ?
C5B C6B N2B C4B 59.2(9) . . . . ?
C1B C2B N2B C6B 61.1(8) . . . . ?
C1B C2B N2B C4B -58.0(8) . . . . ?
C3B C4B N2B C6B -58.3(8) . . . . ?
C3B C4B N2B C2B 60.0(8) . . . . ?
C6S C1S C2S C3S 2.1(10) . . . . ?
I1S C1S C2S C3S -171.7(5) . . . . ?
C6S C1S C2S I2S -175.2(5) . . . . ?
I1S C1S C2S I2S 11.0(9) . . . . ?
C1S C2S C3S F1S -179.4(7) . . . . ?
I2S C2S C3S F1S -1.9(9) . . . . ?
C1S C2S C3S C4S -1.1(11) . . . . ?
I2S C2S C3S C4S 176.4(6) . . . . ?
F1S C3S C4S F2S -2.4(11) . . . . ?
C2S C3S C4S F2S 179.2(7) . . . . ?
F1S C3S C4S C5S 177.3(7) . . . . ?
C2S C3S C4S C5S -1.1(12) . . . . ?
F2S C4S C5S F3S -0.5(12) . . . . ?
C3S C4S C5S F3S 179.7(7) . . . . ?
F2S C4S C5S C6S -178.2(7) . . . . ?
C3S C4S C5S C6S 2.1(12) . . . . ?
F3S C5S C6S F4S -1.1(11) . . . . ?
C4S C5S C6S F4S 176.5(7) . . . . ?
F3S C5S C6S C1S -178.6(7) . . . . ?
C4S C5S C6S C1S -1.0(12) . . . . ?
C2S C1S C6S F4S -178.6(7) . . . . ?
I1S C1S C6S F4S -4.2(9) . . . . ?
C2S C1S C6S C5S -1.1(11) . . . . ?
I1S C1S C6S C5S 173.2(6) . . . . ?
C6T C1T C2T C3T -3.3(10) . . . . ?
I1T C1T C2T C3T 173.0(5) . . . . ?
C6T C1T C2T I2T 175.1(5) . . . . ?
I1T C1T C2T I2T -8.6(9) . . . . ?
C1T C2T C3T F1T 179.8(7) . . . . ?
I2T C2T C3T F1T 1.3(9) . . . . ?
C1T C2T C3T C4T 1.8(11) . . . . ?
I2T C2T C3T C4T -176.6(6) . . . . ?
F1T C3T C4T F2T 2.4(12) . . . . ?
C2T C3T C4T F2T -179.6(8) . . . . ?
F1T C3T C4T C5T -176.8(7) . . . . ?
C2T C3T C4T C5T 1.2(13) . . . . ?
F2T C4T C5T F3T 1.2(13) . . . . ?
C3T C4T C5T F3T -179.5(8) . . . . ?
F2T C4T C5T C6T 178.1(8) . . . . ?
C3T C4T C5T C6T -2.6(13) . . . . ?
F3T C5T C6T F4T -0.1(12) . . . . ?
C4T C5T C6T F4T -176.9(8) . . . . ?
F3T C5T C6T C1T 178.0(8) . . . . ?
C4T C5T C6T C1T 1.1(13) . . . . ?
C2T C1T C6T F4T 179.8(7) . . . . ?
I1T C1T C6T F4T 3.3(10) . . . . ?
C2T C1T C6T C5T 1.9(12) . . . . ?
I1T C1T C6T C5T -174.7(6) . . . . ?

_refine_diff_density_max         2.766
_refine_diff_density_min         -2.170
_refine_diff_density_rms         0.380


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: nitromethane'
