# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_diBrBPA_190k
_database_code_depnum_ccdc_archive 'CCDC 1850139'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_date             2018-01-23T12:09:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H8 Br2 F4 N2'
_chemical_formula_weight         488.08

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.0550(7)
_cell_length_b                   5.2838(2)
_cell_length_c                   11.1874(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.335(3)
_cell_angle_gamma                90
_cell_volume                     828.94(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    3861
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      27.48

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_F_000             472

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.3782
_exptl_absorpt_correction_T_min  0.2660
_shelx_estimated_absorpt_T_min   0.31
_shelx_estimated_absorpt_T_max   0.487

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_number            11101
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.452
_diffrn_reflns_theta_max         31.577
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_number_total             2770
_reflns_number_gt                2061
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0155P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2770
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0523
_refine_ls_wR_factor_gt          0.0496
_refine_ls_goodness_of_fit_ref   0.89
_refine_ls_restrained_S_all      0.89
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.54
_refine_diff_density_rms         0.091

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34177(2) 0.06668(4) 0.35475(2) 0.02266(6) Uani 1 d . .
F1 F 0.53285(8) 0.1866(2) 0.32895(11) 0.0330(3) Uani 1 d . .
C9 C 0.02623(13) 0.0823(3) 0.02867(18) 0.0226(4) Uani 1 d . .
N1 N 0.21084(12) 0.6699(3) 0.23158(16) 0.0281(4) Uani 1 d . .
C1 C 0.43209(13) 0.3166(3) 0.43658(16) 0.0182(4) Uani 1 d . .
C4 C 0.21702(15) 0.5680(4) 0.1258(2) 0.0297(5) Uani 1 d . .
H4 H 0.2647 0.6308 0.0966 0.036 Uiso 1 calc . .
C8 C 0.14371(14) 0.5757(4) 0.27080(19) 0.0270(4) Uani 1 d . .
H8 H 0.1382 0.6443 0.3463 0.032 Uiso 1 calc . .
C2 C 0.51517(14) 0.3433(4) 0.41223(17) 0.0203(4) Uani 1 d . .
C6 C 0.08867(13) 0.2815(3) 0.09775(17) 0.0195(4) Uani 1 d . .
C5 C 0.15870(14) 0.3780(3) 0.05643(19) 0.0252(4) Uani 1 d . .
H5 H 0.166 0.3133 -0.0187 0.03 Uiso 1 calc . .
C7 C 0.08217(14) 0.3855(3) 0.20826(19) 0.0243(4) Uani 1 d . .
H7 H 0.0356 0.3256 0.2403 0.029 Uiso 1 calc . .
F2 F 0.33810(8) 0.4616(2) 0.55079(11) 0.0330(3) Uani 1 d . .
C3 C 0.41858(13) 0.4778(3) 0.52550(18) 0.0203(4) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br1 C1 1.8775(18) . ?
F1 C2 1.343(2) . ?
C9 C9 1.193(4) 3 ?
C9 C6 1.435(2) . ?
N1 C4 1.334(3) . ?
N1 C8 1.336(2) . ?
C1 C3 1.380(2) . ?
C1 C2 1.381(3) . ?
C4 C5 1.373(3) . ?
C4 H4 0.95 . ?
C8 C7 1.374(3) . ?
C8 H8 0.95 . ?
C2 C3 1.367(3) 3_666 ?
C6 C7 1.389(3) . ?
C6 C5 1.393(3) . ?
C5 H5 0.95 . ?
C7 H7 0.95 . ?
F2 C3 1.343(2) . ?
C3 C2 1.367(3) 3_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C9 C6 179.5(3) 3 . ?
C4 N1 C8 116.51(17) . . ?
C3 C1 C2 117.45(17) . . ?
C3 C1 Br1 121.00(14) . . ?
C2 C1 Br1 121.54(14) . . ?
N1 C4 C5 124.04(19) . . ?
N1 C4 H4 118 . . ?
C5 C4 H4 118 . . ?
N1 C8 C7 123.79(18) . . ?
N1 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
F1 C2 C3 119.19(17) . 3_666 ?
F1 C2 C1 119.74(17) . . ?
C3 C2 C1 121.03(17) 3_666 . ?
C7 C6 C5 117.23(17) . . ?
C7 C6 C9 121.67(17) . . ?
C5 C6 C9 121.09(17) . . ?
C4 C5 C6 119.08(18) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C8 C7 C6 119.35(17) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
F2 C3 C2 118.91(16) . 3_666 ?
F2 C3 C1 119.57(17) . . ?
C2 C3 C1 121.51(17) 3_666 . ?

####################################################################### 
# 
# 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_diBrBPA_230k
_database_code_depnum_ccdc_archive 'CCDC 1850141'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_date             2018-01-23T12:19:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H8 Br2 F4 N2'
_chemical_formula_weight         488.08

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.0878(5)
_cell_length_b                   5.2804(2)
_cell_length_c                   11.2408(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.346(2)
_cell_angle_gamma                90
_cell_volume                     834.11(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    229(2)
_cell_measurement_reflns_used    3279
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      28.55

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_F_000             472

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.3782
_exptl_absorpt_correction_T_min  0.2660
_shelx_estimated_absorpt_T_min   0.312
_shelx_estimated_absorpt_T_max   0.489

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      229(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_number            11175
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.449
_diffrn_reflns_theta_max         31.581
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             2791
_reflns_number_gt                1967
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0145P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2791
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.053
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_restrained_S_all      0.869
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.61
_refine_diff_density_rms         0.091

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34218(2) 0.43297(4) 0.85448(2) 0.02815(7) Uani 1 d . .
F2 F 0.33870(8) 0.0401(2) 1.05054(12) 0.0411(3) Uani 1 d . .
C9 C 0.02591(14) 0.4176(3) 0.52866(18) 0.0275(4) Uani 1 d . .
C4 C 0.21632(15) -0.0681(4) 0.6255(2) 0.0364(5) Uani 1 d . .
H4 H 0.2634 -0.1302 0.5969 0.044 Uiso 1 calc . .
C8 C 0.14410(15) -0.0749(4) 0.7696(2) 0.0334(5) Uani 1 d . .
H8 H 0.1392 -0.1416 0.8445 0.04 Uiso 1 calc . .
N1 N 0.21026(12) -0.1700(3) 0.73054(17) 0.0341(4) Uani 1 d . .
C2 C 0.51507(14) 0.1560(4) 0.91245(17) 0.0243(4) Uani 1 d . .
C1 C 0.43227(13) 0.1842(3) 0.93678(17) 0.0222(4) Uani 1 d . .
C6 C 0.08864(13) 0.2181(4) 0.59721(18) 0.0242(4) Uani 1 d . .
C3 C 0.41902(14) 0.0226(4) 1.02545(18) 0.0249(4) Uani 1 d . .
C5 C 0.15811(15) 0.1220(4) 0.5563(2) 0.0304(5) Uani 1 d . .
H5 H 0.1653 0.186 0.4823 0.037 Uiso 1 calc . .
C7 C 0.08213(14) 0.1156(4) 0.70719(19) 0.0299(5) Uani 1 d . .
H7 H 0.0362 0.175 0.7388 0.036 Uiso 1 calc . .
F1 F 0.53290(9) 0.3113(2) 0.82897(11) 0.0403(3) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br1 C1 1.8745(18) . ?
F2 C3 1.344(2) . ?
C9 C9 1.190(4) 3_566 ?
C9 C6 1.438(2) . ?
C4 N1 1.330(3) . ?
C4 C5 1.374(3) . ?
C4 H4 0.94 . ?
C8 N1 1.327(3) . ?
C8 C7 1.379(3) . ?
C8 H8 0.94 . ?
C2 F1 1.345(2) . ?
C2 C3 1.364(3) 3_657 ?
C2 C1 1.381(3) . ?
C1 C3 1.381(3) . ?
C6 C5 1.385(3) . ?
C6 C7 1.385(3) . ?
C3 C2 1.364(3) 3_657 ?
C5 H5 0.94 . ?
C7 H7 0.94 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C9 C6 179.6(3) 3_566 . ?
N1 C4 C5 124.18(19) . . ?
N1 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
N1 C8 C7 124.07(19) . . ?
N1 C8 H8 118 . . ?
C7 C8 H8 118 . . ?
C8 N1 C4 116.33(17) . . ?
F1 C2 C3 119.02(17) . 3_657 ?
F1 C2 C1 119.83(17) . . ?
C3 C2 C1 121.13(17) 3_657 . ?
C2 C1 C3 117.10(18) . . ?
C2 C1 Br1 121.58(14) . . ?
C3 C1 Br1 121.32(15) . . ?
C5 C6 C7 117.46(18) . . ?
C5 C6 C9 121.36(18) . . ?
C7 C6 C9 121.18(18) . . ?
F2 C3 C2 119.04(17) . 3_657 ?
F2 C3 C1 119.18(17) . . ?
C2 C3 C1 121.78(18) 3_657 . ?
C4 C5 C6 119.00(19) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C8 C7 C6 118.94(18) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?

####################################################################### 
# 
# 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_diBrBPA_250k
_database_code_depnum_ccdc_archive 'CCDC 1850142'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_date             2018-01-23T12:23:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H8 Br2 F4 N2'
_chemical_formula_weight         488.08

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.1069(5)
_cell_length_b                   5.2772(2)
_cell_length_c                   11.2674(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.344(2)
_cell_angle_gamma                90
_cell_volume                     836.65(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    249(2)
_cell_measurement_reflns_used    3110
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      27.14

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.937
_exptl_crystal_F_000             472

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.3782
_exptl_absorpt_correction_T_min  0.2660
_shelx_estimated_absorpt_T_min   0.312
_shelx_estimated_absorpt_T_max   0.49

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      249(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_number            11205
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.895
_diffrn_reflns_theta_max         31.557
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             2797
_reflns_number_gt                2121
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²+0.0789P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2797
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.083

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34239(2) 0.43268(4) 0.85433(2) 0.03059(7) Uani 1 d . .
F2 F 0.33872(9) 0.0401(3) 1.05015(13) 0.0448(3) Uani 1 d . .
F1 F 0.53271(9) 0.3103(3) 0.82933(12) 0.0439(3) Uani 1 d . .
C9 C 0.02589(14) 0.4176(4) 0.52849(19) 0.0303(4) Uani 1 d . .
C4 C 0.21623(16) -0.0676(4) 0.6252(2) 0.0397(5) Uani 1 d . .
H4 H 0.2633 -0.1298 0.5966 0.048 Uiso 1 calc . .
C1 C 0.43255(13) 0.1835(4) 0.93652(16) 0.0248(4) Uani 1 d . .
N1 N 0.21017(13) -0.1697(4) 0.73002(18) 0.0378(4) Uani 1 d . .
C8 C 0.14384(16) -0.0754(4) 0.7687(2) 0.0374(5) Uani 1 d . .
H8 H 0.1386 -0.1434 0.8429 0.045 Uiso 1 calc . .
C2 C 0.51529(14) 0.1561(4) 0.91261(17) 0.0275(4) Uani 1 d . .
C6 C 0.08857(13) 0.2185(4) 0.59688(17) 0.0271(4) Uani 1 d . .
C3 C 0.41876(14) 0.0240(4) 1.02511(18) 0.0276(4) Uani 1 d . .
C5 C 0.15806(15) 0.1231(4) 0.5562(2) 0.0338(5) Uani 1 d . .
H5 H 0.1654 0.1875 0.4825 0.041 Uiso 1 calc . .
C7 C 0.08219(15) 0.1158(4) 0.7070(2) 0.0331(5) Uani 1 d . .
H7 H 0.0366 0.1756 0.7388 0.04 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br1 C1 1.8771(18) . ?
F2 C3 1.341(2) . ?
F1 C2 1.338(2) . ?
C9 C9 1.190(4) 3_566 ?
C9 C6 1.436(3) . ?
C4 N1 1.331(3) . ?
C4 C5 1.376(3) . ?
C4 H4 0.94 . ?
C1 C3 1.378(3) . ?
C1 C2 1.379(3) . ?
N1 C8 1.326(3) . ?
C8 C7 1.377(3) . ?
C8 H8 0.94 . ?
C2 C3 1.371(3) 3_657 ?
C6 C5 1.384(3) . ?
C6 C7 1.389(3) . ?
C3 C2 1.371(3) 3_657 ?
C5 H5 0.94 . ?
C7 H7 0.94 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C9 C6 179.8(3) 3_566 . ?
N1 C4 C5 124.2(2) . . ?
N1 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C3 C1 C2 117.66(18) . . ?
C3 C1 Br1 120.76(15) . . ?
C2 C1 Br1 121.58(15) . . ?
C8 N1 C4 116.34(18) . . ?
N1 C8 C7 124.2(2) . . ?
N1 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
F1 C2 C3 119.25(18) . 3_657 ?
F1 C2 C1 119.79(18) . . ?
C3 C2 C1 120.95(18) 3_657 . ?
C5 C6 C7 117.46(18) . . ?
C5 C6 C9 121.32(18) . . ?
C7 C6 C9 121.22(18) . . ?
F2 C3 C2 118.65(17) . 3_657 ?
F2 C3 C1 119.95(18) . . ?
C2 C3 C1 121.39(18) 3_657 . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C8 C7 C6 118.87(19) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?

####################################################################### 
# 
# 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_diBrBPA_210k
_database_code_depnum_ccdc_archive 'CCDC 1850140'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_date             2018-01-23T12:10:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H8 Br2 F4 N2'
_chemical_formula_weight         488.08

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.0775(9)
_cell_length_b                   5.2848(3)
_cell_length_c                   11.2151(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.405(4)
_cell_angle_gamma                90
_cell_volume                     832.00(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    209(2)
_cell_measurement_reflns_used    3476
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      28.69

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.948
_exptl_crystal_F_000             472

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.3782
_exptl_absorpt_correction_T_min  0.2660
_shelx_estimated_absorpt_T_min   0.311
_shelx_estimated_absorpt_T_max   0.489

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      209(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_number            11083
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.451
_diffrn_reflns_theta_max         31.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_number_total             2777
_reflns_number_gt                2010
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0146P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2777
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.052
_refine_ls_wR_factor_gt          0.0493
_refine_ls_goodness_of_fit_ref   0.87
_refine_ls_restrained_S_all      0.87
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.086

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34196(2) 0.43311(4) 0.85463(2) 0.02541(7) Uani 1 d . .
F2 F 0.33850(8) 0.0393(2) 1.05057(11) 0.0369(3) Uani 1 d . .
F1 F 0.53278(8) 0.3118(2) 0.82899(11) 0.0364(3) Uani 1 d . .
C1 C 0.43208(13) 0.1836(3) 0.93659(16) 0.0203(4) Uani 1 d . .
C2 C 0.51517(14) 0.1567(4) 0.91256(17) 0.0230(4) Uani 1 d . .
C3 C 0.41854(13) 0.0223(3) 1.02528(18) 0.0226(4) Uani 1 d . .
C9 C 0.02619(13) 0.4175(3) 0.52884(18) 0.0255(4) Uani 1 d . .
N1 N 0.21074(12) -0.1701(3) 0.73133(16) 0.0311(4) Uani 1 d . .
C8 C 0.14366(14) -0.0755(4) 0.77019(19) 0.0300(4) Uani 1 d . .
H8 H 0.1382 -0.1435 0.8447 0.036 Uiso 1 calc . .
C6 C 0.08848(13) 0.2185(3) 0.59728(17) 0.0220(4) Uani 1 d . .
C4 C 0.21682(15) -0.0678(4) 0.6260(2) 0.0321(5) Uani 1 d . .
H4 H 0.264 -0.1295 0.5973 0.038 Uiso 1 calc . .
C5 C 0.15849(14) 0.1220(4) 0.55662(19) 0.0281(5) Uani 1 d . .
H5 H 0.1658 0.186 0.4825 0.034 Uiso 1 calc . .
C7 C 0.08197(14) 0.1154(3) 0.70792(19) 0.0269(4) Uani 1 d . .
H7 H 0.0362 0.1752 0.7397 0.032 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br1 C1 1.8758(18) . ?
F2 C3 1.340(2) . ?
F1 C2 1.343(2) . ?
C1 C3 1.380(3) . ?
C1 C2 1.382(3) . ?
C2 C3 1.368(3) 3_657 ?
C3 C2 1.368(3) 3_657 ?
C9 C9 1.196(4) 3_566 ?
C9 C6 1.432(2) . ?
N1 C4 1.332(3) . ?
N1 C8 1.336(3) . ?
C8 C7 1.377(3) . ?
C8 H8 0.94 . ?
C6 C5 1.390(3) . ?
C6 C7 1.391(3) . ?
C4 C5 1.373(3) . ?
C4 H4 0.94 . ?
C5 H5 0.94 . ?
C7 H7 0.94 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 117.41(17) . . ?
C3 C1 Br1 121.07(14) . . ?
C2 C1 Br1 121.52(14) . . ?
F1 C2 C3 118.95(17) . 3_657 ?
F1 C2 C1 119.87(17) . . ?
C3 C2 C1 121.16(17) 3_657 . ?
F2 C3 C2 119.05(16) . 3_657 ?
F2 C3 C1 119.51(17) . . ?
C2 C3 C1 121.43(17) 3_657 . ?
C9 C9 C6 179.6(3) 3_566 . ?
C4 N1 C8 116.27(17) . . ?
N1 C8 C7 124.08(18) . . ?
N1 C8 H8 118 . . ?
C7 C8 H8 118 . . ?
C5 C6 C7 117.27(17) . . ?
C5 C6 C9 121.42(17) . . ?
C7 C6 C9 121.31(17) . . ?
N1 C4 C5 124.17(19) . . ?
N1 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C4 C5 C6 119.20(18) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C8 C7 C6 119.00(18) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?

####################################################################### 
# 
# 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_diBrBPA_270k
_database_code_depnum_ccdc_archive 'CCDC 1850143'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_date             2018-01-23T12:36:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H8 Br2 F4 N2'
_chemical_formula_weight         488.08

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.1283(5)
_cell_length_b                   5.27450(10)
_cell_length_c                   11.2948(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.348(2)
_cell_angle_gamma                90
_cell_volume                     839.42(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    269(2)
_cell_measurement_reflns_used    3012
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      26.85

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_F_000             472

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.3782
_exptl_absorpt_correction_T_min  0.2660
_shelx_estimated_absorpt_T_min   0.313
_shelx_estimated_absorpt_T_max   0.491

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      269(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_number            11249
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.891
_diffrn_reflns_theta_max         31.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             2808
_reflns_number_gt                2098
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+0.2006P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2808
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0664
_refine_ls_wR_factor_gt          0.0596
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.082

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34259(2) 0.43240(4) 0.85417(2) 0.03354(8) Uani 1 d . .
F2 F 0.33902(10) 0.0412(3) 1.05004(14) 0.0486(4) Uani 1 d . .
F1 F 0.53282(10) 0.3093(3) 0.82938(12) 0.0478(4) Uani 1 d . .
C9 C 0.02601(15) 0.4177(4) 0.5284(2) 0.0329(4) Uani 1 d . .
C4 C 0.21602(17) -0.0678(4) 0.6251(2) 0.0430(6) Uani 1 d . .
H4 H 0.2624 -0.1298 0.5968 0.052 Uiso 1 calc . .
C1 C 0.43252(14) 0.1840(4) 0.93641(17) 0.0277(4) Uani 1 d . .
C8 C 0.14395(17) -0.0750(4) 0.7684(2) 0.0406(5) Uani 1 d . .
H8 H 0.1389 -0.1421 0.8419 0.049 Uiso 1 calc . .
N1 N 0.21008(14) -0.1689(4) 0.72957(19) 0.0415(5) Uani 1 d . .
C2 C 0.51499(15) 0.1557(4) 0.91250(18) 0.0297(4) Uani 1 d . .
C6 C 0.08863(14) 0.2188(4) 0.59652(18) 0.0296(4) Uani 1 d . .
C3 C 0.41895(15) 0.0240(4) 1.02509(19) 0.0304(4) Uani 1 d . .
C5 C 0.15786(16) 0.1230(4) 0.5560(2) 0.0371(5) Uani 1 d . .
H5 H 0.1651 0.1864 0.4832 0.045 Uiso 1 calc . .
C7 C 0.08212(16) 0.1160(4) 0.7065(2) 0.0363(5) Uani 1 d . .
H7 H 0.0369 0.1751 0.7377 0.044 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br1 C1 1.873(2) . ?
F2 C3 1.341(2) . ?
F1 C2 1.340(2) . ?
C9 C9 1.190(4) 3_566 ?
C9 C6 1.435(3) . ?
C4 N1 1.327(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.93 . ?
C1 C2 1.377(3) . ?
C1 C3 1.381(3) . ?
C8 N1 1.326(3) . ?
C8 C7 1.380(3) . ?
C8 H8 0.93 . ?
C2 C3 1.371(3) 3_657 ?
C6 C5 1.382(3) . ?
C6 C7 1.391(3) . ?
C3 C2 1.371(3) 3_657 ?
C5 H5 0.93 . ?
C7 H7 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C9 C6 179.8(4) 3_566 . ?
N1 C4 C5 124.2(2) . . ?
N1 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C2 C1 C3 117.41(18) . . ?
C2 C1 Br1 121.66(15) . . ?
C3 C1 Br1 120.93(15) . . ?
N1 C8 C7 124.0(2) . . ?
N1 C8 H8 118 . . ?
C7 C8 H8 118 . . ?
C8 N1 C4 116.60(19) . . ?
F1 C2 C3 118.89(19) . 3_657 ?
F1 C2 C1 119.97(19) . . ?
C3 C2 C1 121.12(19) 3_657 . ?
C5 C6 C7 117.51(19) . . ?
C5 C6 C9 121.4(2) . . ?
C7 C6 C9 121.07(19) . . ?
F2 C3 C2 118.87(18) . 3_657 ?
F2 C3 C1 119.65(19) . . ?
C2 C3 C1 121.47(19) 3_657 . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C8 C7 C6 118.8(2) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?

####################################################################### 
# 
# 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_diIBPA_190k
_database_code_depnum_ccdc_archive 'CCDC 1850144'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT094_diIBPA_190k         
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.34 Report
RESPONSE: Due to absorption correction issues about the iodine atoms.
;
_vrf_PLAT334_diIBPA_190k         
;
PROBLEM: Small Aver. Benzene C-C Dist C1       -C2_c            1.37 Ang.  
RESPONSE: ... 
;
_vrf_PLAT971_diIBPA_190k         
;
PROBLEM: Check Calcd Resid. Dens.  0.71A   From I1              2.28 eA-3  
RESPONSE: Due to absorption corrections issues.
;
_vrf_PLAT975_diIBPA_190k         
;
PROBLEM: Check Calcd Resid. Dens.  0.80A   From N1              0.45 eA-3  
RESPONSE: Due to absorption corrections issues.
;
# end Validation Reply Form

_audit_creation_date             2018-05-08T15:00:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H8 F4 I2 N2'
_chemical_formula_weight         582.06

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n n m'
_symmetry_space_group_name_Hall  '-P 2 2n'
_symmetry_Int_Tables_number      58
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.6409(8)
_cell_length_b                   5.2384(3)
_cell_length_c                   11.0229(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     903.14(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    191(2)
_cell_measurement_reflns_used    3618
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      31.12

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.067
_exptl_crystal_density_diffrn    2.14
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.7287
_shelx_estimated_absorpt_T_min   0.32
_shelx_estimated_absorpt_T_max   0.798

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      191(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_number            9683
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         31.562
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_number_total             1574
_reflns_number_gt                1460
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1574
_refine_ls_number_parameters     67
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.393
_refine_diff_density_min         -1.021
_refine_diff_density_rms         0.186

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.84111(2) 0.97451(4) 0.5 0.02193(9) Uani 1 d . .
F1 F 0.93972(10) 0.6781(4) 0.71339(11) 0.0493(4) Uani 1 d . .
N1 N 0.71648(15) 0.3456(5) 0.5 0.0297(5) Uani 1 d . .
C1 C 0.93583(15) 0.6900(5) 0.5 0.0198(5) Uani 1 d . .
C2 C 0.96865(13) 0.5931(5) 0.60598(18) 0.0252(4) Uani 1 d . .
C5 C 0.59135(16) 0.7249(5) 0.5 0.0235(5) Uani 1 d . .
C3 C 0.68577(18) 0.4397(5) 0.6030(3) 0.0347(5) Uani 1 d . .
H3 H 0.7077 0.3755 0.6774 0.042 Uiso 1 calc . .
C4 C 0.62321(13) 0.6274(5) 0.60716(19) 0.0306(5) Uani 1 d . .
H4 H 0.6026 0.6881 0.6829 0.037 Uiso 1 calc . .
C6 C 0.5272(2) 0.9183(7) 0.5 0.0270(6) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.102(2) . ?
F1 C2 1.343(2) . ?
N1 C3 1.327(3) 6_556 ?
N1 C3 1.327(3) . ?
C1 C2 1.373(2) . ?
C1 C2 1.373(2) 6_556 ?
C2 C2 1.383(4) 2_765 ?
C5 C4 1.380(2) . ?
C5 C4 1.380(2) 6_556 ?
C5 C6 1.426(4) . ?
C3 C4 1.388(3) . ?
C3 H3 0.95 . ?
C4 H4 0.95 . ?
C6 C6 1.207(7) 5_676 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C3 117.5(3) 6_556 . ?
C2 C1 C2 116.6(2) . 6_556 ?
C2 C1 I1 121.72(12) . . ?
C2 C1 I1 121.72(12) 6_556 . ?
F1 C2 C1 120.08(18) . . ?
F1 C2 C2 118.20(11) . 2_765 ?
C1 C2 C2 121.72(12) . 2_765 ?
C4 C5 C4 117.7(3) . 6_556 ?
C4 C5 C6 121.13(13) . . ?
C4 C5 C6 121.13(13) 6_556 . ?
N1 C3 C4 123.1(2) . . ?
N1 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C6 C6 C5 179.9(5) 5_676 . ?

####################################################################### 
# 
# 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_diIBPA_210k
_database_code_depnum_ccdc_archive 'CCDC 1850145'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_date             2018-05-08T15:00:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H8 F4 I2 N2'
_chemical_formula_weight         582.06

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n n m'
_symmetry_space_group_name_Hall  '-P 2 2n'
_symmetry_Int_Tables_number      58
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.6537(5)
_cell_length_b                   5.2381(2)
_cell_length_c                   11.0524(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     906.25(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    211(2)
_cell_measurement_reflns_used    6346
_cell_measurement_theta_min      3.69
_cell_measurement_theta_max      31.54

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.067
_exptl_crystal_density_diffrn    2.133
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.7287
_shelx_estimated_absorpt_T_min   0.321
_shelx_estimated_absorpt_T_max   0.799

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      211(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_number            9715
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.256
_diffrn_reflns_theta_max         31.566
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             1584
_reflns_number_gt                1478
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0162P)²+0.3282P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1584
_refine_ls_number_parameters     67
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0166
_refine_ls_wR_factor_ref         0.0415
_refine_ls_wR_factor_gt          0.0406
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.106

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.84110(2) 0.47394(2) 0.5 0.02460(5) Uani 1 d . .
C6 C 0.52683(15) 0.4197(4) 0.5 0.0286(4) Uani 1 d . .
F1 F 0.93989(8) 0.1781(3) 0.71272(9) 0.0530(3) Uani 1 d . .
N1 N 0.71612(12) -0.1546(4) 0.5 0.0334(4) Uani 1 d . .
C2 C 0.96862(10) 0.0932(3) 0.60573(13) 0.0275(3) Uani 1 d . .
C1 C 0.93582(12) 0.1901(4) 0.5 0.0217(4) Uani 1 d . .
C5 C 0.59119(13) 0.2241(4) 0.5 0.0263(4) Uani 1 d . .
C4 C 0.62304(11) 0.1275(3) 0.60736(16) 0.0338(3) Uani 1 d . .
H4 H 0.6029 0.1884 0.6821 0.041 Uiso 1 calc . .
C3 C 0.68539(12) -0.0610(3) 0.60280(18) 0.0372(4) Uani 1 d . .
H3 H 0.7069 -0.1255 0.6761 0.045 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.0998(18) . ?
C6 C6 1.189(5) 5_666 ?
C6 C5 1.437(3) . ?
F1 C2 1.3410(17) . ?
N1 C3 1.328(2) . ?
N1 C3 1.328(2) 6_556 ?
C2 C1 1.3736(18) . ?
C2 C2 1.385(3) 2_755 ?
C1 C2 1.3736(18) 6_556 ?
C5 C4 1.3829(19) 6_556 ?
C5 C4 1.3830(19) . ?
C4 C3 1.390(2) . ?
C4 H4 0.94 . ?
C3 H3 0.94 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C6 C5 179.6(3) 5_666 . ?
C3 N1 C3 117.7(2) . 6_556 ?
F1 C2 C1 120.15(13) . . ?
F1 C2 C2 118.14(8) . 2_755 ?
C1 C2 C2 121.70(9) . 2_755 ?
C2 C1 C2 116.59(17) 6_556 . ?
C2 C1 I1 121.71(9) 6_556 . ?
C2 C1 I1 121.71(9) . . ?
C4 C5 C4 118.19(19) 6_556 . ?
C4 C5 C6 120.91(10) 6_556 . ?
C4 C5 C6 120.91(10) . . ?
C5 C4 C3 118.83(16) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C3 C4 123.24(17) . . ?
N1 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?

####################################################################### 
# 
# 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_diIBPA_270k
_database_code_depnum_ccdc_archive 'CCDC 1850148'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_date             2018-05-08T15:01:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H8 F4 I2 N2'
_chemical_formula_weight         582.06

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n n m'
_symmetry_space_group_name_Hall  '-P 2 2n'
_symmetry_Int_Tables_number      58
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.6966(9)
_cell_length_b                   5.2398(3)
_cell_length_c                   11.1314(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     915.52(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    276(2)
_cell_measurement_reflns_used    5756
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      31.45

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.067
_exptl_crystal_density_diffrn    2.111
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.7287
_shelx_estimated_absorpt_T_min   0.324
_shelx_estimated_absorpt_T_max   0.8

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      276(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_number            9793
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.243
_diffrn_reflns_theta_max         31.545
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_number_total             1598
_reflns_number_gt                1468
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0203P)²+0.2705P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1598
_refine_ls_number_parameters     67
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0182
_refine_ls_wR_factor_ref         0.0461
_refine_ls_wR_factor_gt          0.0448
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.84116(2) 0.97263(3) 0.5 0.03289(6) Uani 1 d . .
C6 C 0.52652(16) 0.9199(5) 0.5 0.0368(5) Uani 1 d . .
F1 F 0.93992(9) 0.6775(3) 0.71098(10) 0.0692(4) Uani 1 d . .
C2 C 0.96861(11) 0.5928(3) 0.60475(15) 0.0353(3) Uani 1 d . .
C1 C 0.93597(13) 0.6892(4) 0.5 0.0283(4) Uani 1 d . .
C5 C 0.59090(14) 0.7242(4) 0.5 0.0345(5) Uani 1 d . .
C4 C 0.62264(12) 0.6272(4) 0.60622(18) 0.0443(4) Uani 1 d . .
H4 H 0.6028 0.6872 0.6797 0.053 Uiso 1 calc . .
N1 N 0.71518(13) 0.3455(4) 0.5 0.0434(5) Uani 1 d . .
C3 C 0.68461(14) 0.4388(4) 0.6016(2) 0.0485(5) Uani 1 d . .
H3 H 0.7057 0.3748 0.6736 0.058 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.103(2) . ?
C6 C6 1.182(5) 5_676 ?
C6 C5 1.440(3) . ?
F1 C2 1.3410(19) . ?
C2 C1 1.3700(19) . ?
C2 C2 1.385(3) 2_765 ?
C1 C2 1.3700(19) 6_556 ?
C5 C4 1.380(2) 6_556 ?
C5 C4 1.380(2) . ?
C4 C3 1.387(3) . ?
C4 H4 0.93 . ?
N1 C3 1.322(3) . ?
N1 C3 1.322(3) 6_556 ?
C3 H3 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C6 C5 179.8(4) 5_676 . ?
F1 C2 C1 120.20(14) . . ?
F1 C2 C2 118.14(9) . 2_765 ?
C1 C2 C2 121.67(9) . 2_765 ?
C2 C1 C2 116.66(19) 6_556 . ?
C2 C1 I1 121.67(9) 6_556 . ?
C2 C1 I1 121.67(9) . . ?
C4 C5 C4 117.9(2) 6_556 . ?
C4 C5 C6 121.05(11) 6_556 . ?
C4 C5 C6 121.05(11) . . ?
C5 C4 C3 118.92(18) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C3 N1 C3 117.6(2) . 6_556 ?
N1 C3 C4 123.33(19) . . ?
N1 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?

####################################################################### 
# 
# 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_TBrB_BPA_210k
_database_code_depnum_ccdc_archive 'CCDC 1850150'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT341_TBrB_BPA_210k       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.007 Ang.  
RESPONSE: Due to weak high angle data.
;
_vrf_PLAT911_TBrB_BPA_210k       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
RESPONSE: These reflections were not collected.
;
_vrf_PLAT971_TBrB_BPA_210k       
;
PROBLEM: Check Calcd Resid. Dens.  0.86A   From Br1             1.52 eA-3  
RESPONSE: Due to issues with the absorption correction.
;
_vrf_PLAT972_TBrB_BPA_210k       
;
PROBLEM: Check Calcd Resid. Dens.  0.85A   From Br2            -2.28 eA-3  
RESPONSE: Due to issues with the absorption correction.
;
_vrf_PLAT978_TBrB_BPA_210k       
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The residual electron density was surrounding the halides.
;
# end Validation Reply Form

_audit_creation_date             2018-04-23T11:02:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H10 Br4 N2'
_chemical_formula_weight         573.92

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9366(3)
_cell_length_b                   13.2445(10)
_cell_length_c                   18.2177(16)
_cell_angle_alpha                72.763(2)
_cell_angle_beta                 85.794(2)
_cell_angle_gamma                83.955(2)
_cell_volume                     901.25(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    209(2)
_cell_measurement_reflns_used    4480
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.12

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.092
_exptl_crystal_density_diffrn    2.115
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.1256
_exptl_absorpt_correction_T_min  0.0679
_shelx_estimated_absorpt_T_min   0.095
_shelx_estimated_absorpt_T_max   0.494

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      209(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_number            10293
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.616
_diffrn_reflns_theta_max         28.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_number_total             4471
_reflns_number_gt                3312
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0718P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4471
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.471
_refine_diff_density_min         -2.15
_refine_diff_density_rms         0.23

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.84342(13) 0.80566(4) 0.13769(3) 0.03836(16) Uani 1 d . .
Br2 Br 0.71063(14) 0.77166(4) -0.03345(3) 0.04131(16) Uani 1 d . .
Br3 Br 0.27391(13) 0.27786(4) 0.48149(3) 0.03645(16) Uani 1 d . .
Br4 Br 0.28944(13) 0.31600(4) 0.65618(3) 0.03766(16) Uani 1 d . .
N1 N 0.1190(12) -0.0393(4) 0.7692(3) 0.0441(11) Uani 1 d . .
N2 N 0.2624(11) 0.4531(3) 0.2645(3) 0.0390(10) Uani 1 d . .
C1 C 0.2621(14) -0.1111(4) 0.7363(3) 0.0436(13) Uani 1 d . .
H1 H 0.388279 -0.170833 0.76719 0.052 Uiso 1 calc . .
C2 C 0.2385(13) -0.1042(4) 0.6597(3) 0.0381(12) Uani 1 d . .
H2 H 0.346824 -0.157488 0.639492 0.046 Uiso 1 calc . .
C3 C 0.0525(11) -0.0172(4) 0.6132(3) 0.0334(11) Uani 1 d . .
C4 C -0.1007(12) 0.0591(4) 0.6471(3) 0.0350(11) Uani 1 d . .
H4 H -0.229141 0.119559 0.617757 0.042 Uiso 1 calc . .
C5 C -0.0615(13) 0.0447(4) 0.7236(3) 0.0387(12) Uani 1 d . .
H5 H -0.166983 0.096582 0.74556 0.046 Uiso 1 calc . .
C6 C 0.0178(13) -0.0058(4) 0.5333(3) 0.0360(11) Uani 1 d . .
C7 C 0.5614(11) 1.0147(3) 0.0701(3) 0.0281(10) Uani 1 d . .
H7 H 0.605105 1.024696 0.117352 0.034 Uiso 1 calc . .
C8 C 0.6469(11) 0.9169(3) 0.0573(3) 0.0266(9) Uani 1 d . .
C9 C 0.5892(11) 0.9022(3) -0.0126(3) 0.0282(10) Uani 1 d . .
C10 C 0.1250(14) 0.3773(4) 0.2430(3) 0.0393(12) Uani 1 d . .
H10 H 0.078473 0.314558 0.281519 0.047 Uiso 1 calc . .
C11 C 0.0488(12) 0.3856(4) 0.1692(3) 0.0339(11) Uani 1 d . .
H11 H -0.048228 0.330195 0.158124 0.041 Uiso 1 calc . .
C12 C 0.1168(11) 0.4767(4) 0.1110(3) 0.0292(10) Uani 1 d . .
C13 C 0.2606(12) 0.5569(4) 0.1315(3) 0.0348(11) Uani 1 d . .
H13 H 0.309863 0.620342 0.094075 0.042 Uiso 1 calc . .
C14 C 0.3275(13) 0.5408(4) 0.2073(3) 0.0407(13) Uani 1 d . .
H14 H 0.425531 0.594796 0.220089 0.049 Uiso 1 calc . .
C15 C 0.0344(12) 0.4929(4) 0.0323(3) 0.0310(10) Uani 1 d . .
C16 C 0.4920(11) 0.4849(3) 0.4274(3) 0.0292(10) Uani 1 d . .
H16 H 0.485162 0.474373 0.378728 0.035 Uiso 1 calc . .
C17 C 0.4028(10) 0.4061(3) 0.4937(3) 0.0267(10) Uani 1 d . .
C18 C 0.4092(11) 0.4210(3) 0.5659(3) 0.0269(9) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br1 C8 1.887(4) . ?
Br2 C9 1.884(4) . ?
Br3 C17 1.901(4) . ?
Br4 C18 1.879(5) . ?
N1 C1 1.326(7) . ?
N1 C5 1.344(7) . ?
N2 C14 1.344(7) . ?
N2 C10 1.353(6) . ?
C1 C2 1.380(7) . ?
C1 H1 0.94 . ?
C2 C3 1.384(7) . ?
C2 H2 0.94 . ?
C3 C4 1.399(7) . ?
C3 C6 1.432(7) . ?
C4 C5 1.367(7) . ?
C4 H4 0.94 . ?
C5 H5 0.94 . ?
C6 C6 1.195(10) 2_556 ?
C7 C8 1.386(6) . ?
C7 C9 1.390(6) 2_675 ?
C7 H7 0.94 . ?
C8 C9 1.381(6) . ?
C10 C11 1.370(7) . ?
C10 H10 0.94 . ?
C11 C12 1.385(7) . ?
C11 H11 0.94 . ?
C12 C13 1.407(6) . ?
C12 C15 1.443(6) . ?
C13 C14 1.375(7) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C15 1.182(9) 2_565 ?
C16 C17 1.392(6) . ?
C16 C18 1.386(6) 2_666 ?
C16 H16 0.94 . ?
C17 C18 1.389(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.3(5) . . ?
C14 N2 C10 115.5(4) . . ?
N1 C1 C2 124.5(5) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 118.8(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 117.4(5) . . ?
C2 C3 C6 121.3(5) . . ?
C4 C3 C6 121.3(5) . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 123.9(5) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C6 C6 C3 178.2(7) 2_556 . ?
C8 C7 C9 119.6(4) . 2_675 ?
C8 C7 H7 120.2 . . ?
C9 C7 H7 120.2 2_675 . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 Br1 121.5(3) . . ?
C7 C8 Br1 118.1(3) . . ?
C8 C9 C7 119.9(4) . 2_675 ?
C8 C9 Br2 122.0(4) . . ?
C7 C9 Br2 118.1(3) 2_675 . ?
N2 C10 C11 124.6(5) . . ?
N2 C10 H10 117.7 . . ?
C11 C10 H10 117.7 . . ?
C10 C11 C12 119.1(4) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 117.6(4) . . ?
C11 C12 C15 122.5(4) . . ?
C13 C12 C15 119.9(5) . . ?
C14 C13 C12 118.7(5) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
N2 C14 C13 124.4(5) . . ?
N2 C14 H14 117.8 . . ?
C13 C14 H14 117.8 . . ?
C15 C15 C12 179.4(7) 2_565 . ?
C17 C16 C18 119.1(4) . 2_666 ?
C17 C16 H16 120.4 . . ?
C18 C16 H16 120.4 2_666 . ?
C18 C17 C16 121.0(4) . . ?
C18 C17 Br3 121.5(4) . . ?
C16 C17 Br3 117.5(3) . . ?
C17 C18 C16 119.9(4) . 2_666 ?
C17 C18 Br4 121.8(3) . . ?
C16 C18 Br4 118.3(4) 2_666 . ?

####################################################################### 
# 
# 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_TBrB_BPA_190k
_database_code_depnum_ccdc_archive 'CCDC 1850149'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT341_TBrB_BPA_190k       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00694 Ang.  
RESPONSE: Due to weak high angle data.
;
_vrf_PLAT911_TBrB_BPA_190k       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
RESPONSE: These reflections were not collected.
;
_vrf_PLAT971_TBrB_BPA_190k       
;
PROBLEM: Check Calcd Resid. Dens.  0.85A   From Br4             1.79 eA-3  
RESPONSE: Due to issues with the absorption correction.
;
_vrf_PLAT972_TBrB_BPA_190k       
;
PROBLEM: Check Calcd Resid. Dens.  0.86A   From Br2            -2.15 eA-3  
RESPONSE: Due to issues with the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2018-04-23T11:02:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H10 Br4 N2'
_chemical_formula_weight         573.92

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9272(3)
_cell_length_b                   13.2313(11)
_cell_length_c                   18.2212(16)
_cell_angle_alpha                72.682(2)
_cell_angle_beta                 85.789(2)
_cell_angle_gamma                83.900(2)
_cell_volume                     897.90(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    189(2)
_cell_measurement_reflns_used    4749
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.21

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.092
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.1256
_exptl_absorpt_correction_T_min  0.0679
_shelx_estimated_absorpt_T_min   0.095
_shelx_estimated_absorpt_T_max   0.493

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      189(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_number            10236
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.619
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_number_total             4453
_reflns_number_gt                3418
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4453
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.719
_refine_diff_density_min         -2.174
_refine_diff_density_rms         0.224

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.84540(13) 0.80571(4) 0.13805(3) 0.03391(15) Uani 1 d . .
Br2 Br 0.71502(14) 0.77130(4) -0.03309(3) 0.03628(16) Uani 1 d . .
Br3 Br 0.27347(12) 0.27758(4) 0.48163(3) 0.03212(15) Uani 1 d . .
Br4 Br 0.28918(13) 0.31565(4) 0.65634(3) 0.03316(15) Uani 1 d . .
N1 N 0.1184(12) -0.0398(3) 0.7694(2) 0.0383(10) Uani 1 d . .
N2 N 0.2636(11) 0.4529(3) 0.2645(2) 0.0360(10) Uani 1 d . .
C1 C 0.2650(14) -0.1115(4) 0.7364(3) 0.0391(12) Uani 1 d . .
H1 H 0.396118 -0.171272 0.767531 0.047 Uiso 1 calc . .
C2 C 0.2397(12) -0.1049(4) 0.6600(3) 0.0342(11) Uani 1 d . .
H2 H 0.347503 -0.159265 0.639814 0.041 Uiso 1 calc . .
C3 C 0.0534(11) -0.0171(4) 0.6131(3) 0.0291(10) Uani 1 d . .
C4 C -0.1004(12) 0.0591(4) 0.6469(3) 0.0330(11) Uani 1 d . .
H4 H -0.230167 0.12035 0.617037 0.04 Uiso 1 calc . .
C5 C -0.0619(13) 0.0447(4) 0.7239(3) 0.0347(11) Uani 1 d . .
H5 H -0.168537 0.097218 0.746025 0.042 Uiso 1 calc . .
C6 C 0.0177(12) -0.0054(4) 0.5334(3) 0.0336(11) Uani 1 d . .
C7 C 0.5613(11) 1.0150(3) 0.0702(3) 0.0255(9) Uani 1 d . .
H7 H 0.605194 1.025099 0.118031 0.031 Uiso 1 calc . .
C8 C 0.6482(11) 0.9172(3) 0.0570(3) 0.0233(9) Uani 1 d . .
C9 C 0.5905(11) 0.9024(3) -0.0127(3) 0.0253(9) Uani 1 d . .
C10 C 0.1268(13) 0.3771(4) 0.2436(3) 0.0361(11) Uani 1 d . .
H10 H 0.080071 0.313592 0.282633 0.043 Uiso 1 calc . .
C11 C 0.0504(12) 0.3855(4) 0.1694(3) 0.0306(10) Uani 1 d . .
H11 H -0.046679 0.32921 0.15832 0.037 Uiso 1 calc . .
C12 C 0.1162(11) 0.4772(3) 0.1106(3) 0.0256(9) Uani 1 d . .
C13 C 0.2632(12) 0.5572(4) 0.1312(3) 0.0297(10) Uani 1 d . .
H13 H 0.316732 0.620996 0.093303 0.036 Uiso 1 calc . .
C14 C 0.3275(13) 0.5411(4) 0.2075(3) 0.0358(12) Uani 1 d . .
H14 H 0.423366 0.596089 0.220653 0.043 Uiso 1 calc . .
C15 C 0.0345(11) 0.4930(4) 0.0322(3) 0.0285(10) Uani 1 d . .
C16 C 0.4921(11) 0.4849(3) 0.4276(3) 0.0261(9) Uani 1 d . .
H16 H 0.48562 0.474332 0.378413 0.031 Uiso 1 calc . .
C17 C 0.4035(11) 0.4060(3) 0.4934(3) 0.0257(9) Uani 1 d . .
C18 C 0.4102(11) 0.4210(3) 0.5659(3) 0.0236(9) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br1 C8 1.893(4) . ?
Br2 C9 1.888(4) . ?
Br3 C17 1.900(4) . ?
Br4 C18 1.882(4) . ?
N1 C1 1.328(7) . ?
N1 C5 1.343(6) . ?
N2 C14 1.343(7) . ?
N2 C10 1.347(6) . ?
C1 C2 1.378(7) . ?
C1 H1 0.95 . ?
C2 C3 1.391(7) . ?
C2 H2 0.95 . ?
C3 C4 1.395(6) . ?
C3 C6 1.431(7) . ?
C4 C5 1.375(7) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 C6 1.197(10) 2_556 ?
C7 C9 1.385(6) 2_675 ?
C7 C8 1.388(6) . ?
C7 H7 0.95 . ?
C8 C9 1.379(6) . ?
C10 C11 1.377(7) . ?
C10 H10 0.95 . ?
C11 C12 1.392(6) . ?
C11 H11 0.95 . ?
C12 C13 1.412(6) . ?
C12 C15 1.437(6) . ?
C13 C14 1.381(7) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 C15 1.178(9) 2_565 ?
C16 C18 1.381(6) 2_666 ?
C16 C17 1.385(6) . ?
C16 H16 0.95 . ?
C17 C18 1.397(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.6(4) . . ?
C14 N2 C10 116.0(4) . . ?
N1 C1 C2 124.4(5) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 118.7(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 117.5(5) . . ?
C2 C3 C6 121.5(4) . . ?
C4 C3 C6 121.0(5) . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 123.5(5) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C6 C6 C3 178.8(7) 2_556 . ?
C9 C7 C8 119.0(4) 2_675 . ?
C9 C7 H7 120.5 2_675 . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 120.8(4) . . ?
C9 C8 Br1 121.6(3) . . ?
C7 C8 Br1 117.6(3) . . ?
C8 C9 C7 120.2(4) . 2_675 ?
C8 C9 Br2 121.7(3) . . ?
C7 C9 Br2 118.1(3) 2_675 . ?
N2 C10 C11 124.2(5) . . ?
N2 C10 H10 117.9 . . ?
C11 C10 H10 117.9 . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 117.0(4) . . ?
C11 C12 C15 122.7(4) . . ?
C13 C12 C15 120.2(4) . . ?
C14 C13 C12 118.8(5) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
N2 C14 C13 124.4(4) . . ?
N2 C14 H14 117.8 . . ?
C13 C14 H14 117.8 . . ?
C15 C15 C12 179.2(6) 2_565 . ?
C18 C16 C17 119.5(4) 2_666 . ?
C18 C16 H16 120.2 2_666 . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.6(4) . . ?
C16 C17 Br3 118.0(3) . . ?
C18 C17 Br3 121.4(4) . . ?
C16 C18 C17 119.8(4) 2_666 . ?
C16 C18 Br4 118.5(3) 2_666 . ?
C17 C18 Br4 121.7(3) . . ?

####################################################################### 
# 
# 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_TBrB_BPA_270k
_database_code_depnum_ccdc_archive 'CCDC 1850153'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT911_TBrB_BPA_270k       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         12 Report
RESPONSE: These reflections were not collected.
;
# end Validation Reply Form

_audit_creation_date             2018-04-23T11:22:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H10 Br4 N2'
_chemical_formula_weight         573.92

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9684(4)
_cell_length_b                   13.2770(14)
_cell_length_c                   18.217(2)
_cell_angle_alpha                73.014(3)
_cell_angle_beta                 85.807(3)
_cell_angle_gamma                84.125(3)
_cell_volume                     912.18(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    269(2)
_cell_measurement_reflns_used    3717
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.01

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.092
_exptl_crystal_density_diffrn    2.09
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.1256
_exptl_absorpt_correction_T_min  0.0679
_shelx_estimated_absorpt_T_min   0.096
_shelx_estimated_absorpt_T_max   0.497

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      269(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_number            10298
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         28.209
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_number_total             4461
_reflns_number_gt                3332
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4461
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.032
_refine_ls_wR_factor_ref         0.074
_refine_ls_wR_factor_gt          0.0678
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.086

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.83782(8) 0.80580(3) 0.13648(2) 0.05534(11) Uani 1 d . .
Br2 Br 0.69819(9) 0.77271(3) -0.03455(2) 0.05960(11) Uani 1 d . .
Br3 Br 0.27450(8) 0.27863(2) 0.48118(2) 0.05241(10) Uani 1 d . .
Br4 Br 0.29055(8) 0.31681(3) 0.65572(2) 0.05425(10) Uani 1 d . .
N1 N 0.1185(7) -0.0385(2) 0.76860(17) 0.0616(8) Uani 1 d . .
N2 N 0.2581(7) 0.4532(2) 0.26362(17) 0.0578(7) Uani 1 d . .
C1 C 0.2606(8) -0.1101(3) 0.7355(2) 0.0594(9) Uani 1 d . .
H1 H 0.385333 -0.168707 0.765756 0.071 Uiso 1 calc . .
C2 C 0.2352(8) -0.1031(2) 0.65914(19) 0.0530(8) Uani 1 d . .
H2 H 0.339886 -0.155781 0.638976 0.064 Uiso 1 calc . .
C3 C 0.0528(7) -0.0172(2) 0.61318(18) 0.0447(7) Uani 1 d . .
C4 C -0.0982(7) 0.0596(2) 0.64639(19) 0.0504(8) Uani 1 d . .
H4 H -0.221164 0.119537 0.617302 0.06 Uiso 1 calc . .
C5 C -0.0596(8) 0.0439(3) 0.7234(2) 0.0556(9) Uani 1 d . .
H5 H -0.165474 0.094379 0.745591 0.067 Uiso 1 calc . .
C6 C 0.0154(8) -0.0051(3) 0.53299(18) 0.0516(8) Uani 1 d . .
C7 C 0.5648(6) 1.0140(2) 0.06996(16) 0.0391(6) Uani 1 d . .
H7 H 0.609694 1.023404 0.116811 0.047 Uiso 1 calc . .
C8 C 0.6469(7) 0.9170(2) 0.05627(16) 0.0383(6) Uani 1 d . .
C9 C 0.5837(7) 0.9036(2) -0.01377(17) 0.0392(6) Uani 1 d . .
C10 C 0.1208(8) 0.3791(3) 0.2421(2) 0.0563(8) Uani 1 d . .
H10 H 0.071304 0.317723 0.280067 0.068 Uiso 1 calc . .
C11 C 0.0478(8) 0.3870(2) 0.16824(19) 0.0503(8) Uani 1 d . .
H11 H -0.045815 0.332013 0.157082 0.06 Uiso 1 calc . .
C12 C 0.1150(7) 0.4776(2) 0.11044(18) 0.0420(7) Uani 1 d . .
C13 C 0.2583(7) 0.5563(2) 0.13138(19) 0.0483(7) Uani 1 d . .
H13 H 0.310304 0.618542 0.094668 0.058 Uiso 1 calc . .
C14 C 0.3211(8) 0.5399(3) 0.2075(2) 0.0569(9) Uani 1 d . .
H14 H 0.414375 0.593375 0.220662 0.068 Uiso 1 calc . .
C15 C 0.0343(7) 0.4930(2) 0.03215(17) 0.0457(7) Uani 1 d . .
C16 C 0.4907(7) 0.4847(2) 0.42785(17) 0.0406(7) Uani 1 d . .
H16 H 0.482801 0.474543 0.37963 0.049 Uiso 1 calc . .
C17 C 0.4031(6) 0.4065(2) 0.49324(17) 0.0379(6) Uani 1 d . .
C18 C 0.4095(6) 0.4216(2) 0.56520(17) 0.0387(6) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br1 C8 1.887(3) . ?
Br2 C9 1.888(3) . ?
Br3 C17 1.898(3) . ?
Br4 C18 1.886(3) . ?
N1 C1 1.327(4) . ?
N1 C5 1.332(4) . ?
N2 C14 1.328(4) . ?
N2 C10 1.336(4) . ?
C1 C2 1.377(5) . ?
C1 H1 0.93 . ?
C2 C3 1.374(4) . ?
C2 H2 0.93 . ?
C3 C4 1.395(4) . ?
C3 C6 1.439(4) . ?
C4 C5 1.375(4) . ?
C4 H4 0.93 . ?
C5 H5 0.93 . ?
C6 C6 1.184(6) 2_556 ?
C7 C9 1.376(4) 2_675 ?
C7 C8 1.385(3) . ?
C7 H7 0.93 . ?
C8 C9 1.382(4) . ?
C10 C11 1.369(4) . ?
C10 H10 0.93 . ?
C11 C12 1.383(4) . ?
C11 H11 0.93 . ?
C12 C13 1.395(4) . ?
C12 C15 1.436(4) . ?
C13 C14 1.378(4) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C15 1.179(6) 2_565 ?
C16 C17 1.381(4) . ?
C16 C18 1.386(3) 2_666 ?
C16 H16 0.93 . ?
C17 C18 1.385(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.1(3) . . ?
C14 N2 C10 115.4(3) . . ?
N1 C1 C2 124.2(3) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.0(3) . . ?
C2 C3 C6 121.9(3) . . ?
C4 C3 C6 120.1(3) . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 H4 121 . . ?
C3 C4 H4 121 . . ?
N1 C5 C4 124.7(3) . . ?
N1 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C6 C6 C3 179.9(5) 2_556 . ?
C9 C7 C8 119.6(3) 2_675 . ?
C9 C7 H7 120.2 2_675 . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 Br1 122.2(2) . . ?
C7 C8 Br1 117.7(2) . . ?
C7 C9 C8 120.3(2) 2_675 . ?
C7 C9 Br2 118.6(2) 2_675 . ?
C8 C9 Br2 121.0(2) . . ?
N2 C10 C11 124.8(3) . . ?
N2 C10 H10 117.6 . . ?
C11 C10 H10 117.6 . . ?
C10 C11 C12 119.2(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 117.2(3) . . ?
C11 C12 C15 122.3(3) . . ?
C13 C12 C15 120.5(3) . . ?
C14 C13 C12 118.6(3) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
N2 C14 C13 124.8(3) . . ?
N2 C14 H14 117.6 . . ?
C13 C14 H14 117.6 . . ?
C15 C15 C12 179.0(4) 2_565 . ?
C17 C16 C18 119.4(3) . 2_666 ?
C17 C16 H16 120.3 . . ?
C18 C16 H16 120.3 2_666 . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 Br3 118.0(2) . . ?
C18 C17 Br3 121.4(2) . . ?
C17 C18 C16 119.9(3) . 2_666 ?
C17 C18 Br4 121.9(2) . . ?
C16 C18 Br4 118.2(2) 2_666 . ?

####################################################################### 
# 
# 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_TBrB_BPA_250k
_database_code_depnum_ccdc_archive 'CCDC 1850152'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_TBrB_BPA_250k       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report
RESPONSE: These reflections were not collected.
;
# end Validation Reply Form

_audit_creation_date             2018-04-23T11:21:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H10 Br4 N2'
_chemical_formula_weight         573.92

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9578(3)
_cell_length_b                   13.2665(11)
_cell_length_c                   18.2186(18)
_cell_angle_alpha                72.926(3)
_cell_angle_beta                 85.798(3)
_cell_angle_gamma                84.065(2)
_cell_volume                     908.60(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    249(2)
_cell_measurement_reflns_used    3982
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.97

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.092
_exptl_crystal_density_diffrn    2.098
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.1256
_exptl_absorpt_correction_T_min  0.0679
_shelx_estimated_absorpt_T_min   0.096
_shelx_estimated_absorpt_T_max   0.496

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      249(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_number            10374
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.612
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_number_total             4510
_reflns_number_gt                3452
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0311P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4510
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.09

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.83978(8) 0.80576(2) 0.13687(2) 0.05014(10) Uani 1 d . .
Br2 Br 0.70221(8) 0.77242(2) -0.03423(2) 0.05394(10) Uani 1 d . .
Br3 Br 0.27421(7) 0.27842(2) 0.48129(2) 0.04736(10) Uani 1 d . .
Br4 Br 0.29001(8) 0.31650(2) 0.65593(2) 0.04899(10) Uani 1 d . .
N1 N 0.1184(7) -0.0389(2) 0.76893(16) 0.0552(7) Uani 1 d . .
N2 N 0.2586(7) 0.4536(2) 0.26373(16) 0.0533(7) Uani 1 d . .
C1 C 0.2621(8) -0.1106(3) 0.7357(2) 0.0549(8) Uani 1 d . .
H1 H 0.390061 -0.169661 0.766181 0.066 Uiso 1 calc . .
C2 C 0.2355(7) -0.1037(2) 0.65964(18) 0.0478(7) Uani 1 d . .
H2 H 0.340559 -0.157298 0.639453 0.057 Uiso 1 calc . .
C3 C 0.0526(6) -0.0172(2) 0.61315(17) 0.0412(7) Uani 1 d . .
C4 C -0.0980(7) 0.0593(2) 0.64668(18) 0.0454(7) Uani 1 d . .
H4 H -0.223914 0.119805 0.6173 0.054 Uiso 1 calc . .
C5 C -0.0589(8) 0.0445(3) 0.72314(19) 0.0503(8) Uani 1 d . .
H5 H -0.163536 0.096323 0.745111 0.06 Uiso 1 calc . .
C6 C 0.0164(7) -0.0052(3) 0.53290(18) 0.0479(7) Uani 1 d . .
C7 C 0.5631(6) 1.0142(2) 0.07040(16) 0.0366(6) Uani 1 d . .
H7 H 0.607168 1.023807 0.117791 0.044 Uiso 1 calc . .
C8 C 0.6468(6) 0.9170(2) 0.05661(16) 0.0344(6) Uani 1 d . .
C9 C 0.5861(6) 0.9033(2) -0.01346(16) 0.0349(6) Uani 1 d . .
C10 C 0.1229(8) 0.3790(2) 0.24253(19) 0.0509(8) Uani 1 d . .
H10 H 0.075059 0.31672 0.281054 0.061 Uiso 1 calc . .
C11 C 0.0485(7) 0.3865(2) 0.16893(18) 0.0462(7) Uani 1 d . .
H11 H -0.04716 0.330908 0.157905 0.055 Uiso 1 calc . .
C12 C 0.1165(7) 0.4779(2) 0.11048(17) 0.0391(6) Uani 1 d . .
C13 C 0.2587(7) 0.5567(2) 0.13089(18) 0.0436(7) Uani 1 d . .
H13 H 0.310123 0.619689 0.0936 0.052 Uiso 1 calc . .
C14 C 0.3231(8) 0.5403(3) 0.2076(2) 0.0518(8) Uani 1 d . .
H14 H 0.419001 0.594225 0.220774 0.062 Uiso 1 calc . .
C15 C 0.0347(7) 0.4930(2) 0.03225(17) 0.0428(7) Uani 1 d . .
C16 C 0.4911(6) 0.4847(2) 0.42777(16) 0.0362(6) Uani 1 d . .
H16 H 0.485207 0.474269 0.379048 0.043 Uiso 1 calc . .
C17 C 0.4021(6) 0.4061(2) 0.49351(16) 0.0343(6) Uani 1 d . .
C18 C 0.4110(6) 0.4210(2) 0.56530(16) 0.0347(6) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br1 C8 1.887(3) . ?
Br2 C9 1.888(2) . ?
Br3 C17 1.895(2) . ?
Br4 C18 1.886(3) . ?
N1 C1 1.331(4) . ?
N1 C5 1.340(4) . ?
N2 C14 1.328(4) . ?
N2 C10 1.334(4) . ?
C1 C2 1.372(4) . ?
C1 H1 0.94 . ?
C2 C3 1.380(4) . ?
C2 H2 0.94 . ?
C3 C4 1.394(4) . ?
C3 C6 1.440(4) . ?
C4 C5 1.366(4) . ?
C4 H4 0.94 . ?
C5 H5 0.94 . ?
C6 C6 1.181(6) 2_556 ?
C7 C9 1.383(4) 2_675 ?
C7 C8 1.388(3) . ?
C7 H7 0.94 . ?
C8 C9 1.382(4) . ?
C10 C11 1.367(4) . ?
C10 H10 0.94 . ?
C11 C12 1.394(4) . ?
C11 H11 0.94 . ?
C12 C13 1.389(4) . ?
C12 C15 1.436(4) . ?
C13 C14 1.389(4) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C15 1.183(6) 2_565 ?
C16 C17 1.388(4) . ?
C16 C18 1.389(3) 2_666 ?
C16 H16 0.94 . ?
C17 C18 1.383(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 115.9(3) . . ?
C14 N2 C10 115.8(3) . . ?
N1 C1 C2 124.2(3) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 117.5(3) . . ?
C2 C3 C6 121.9(3) . . ?
C4 C3 C6 120.6(3) . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 124.5(3) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C6 C6 C3 179.3(5) 2_556 . ?
C9 C7 C8 119.1(3) 2_675 . ?
C9 C7 H7 120.4 2_675 . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 Br1 121.98(19) . . ?
C7 C8 Br1 117.6(2) . . ?
C8 C9 C7 120.5(2) . 2_675 ?
C8 C9 Br2 121.3(2) . . ?
C7 C9 Br2 118.2(2) 2_675 . ?
N2 C10 C11 124.8(3) . . ?
N2 C10 H10 117.6 . . ?
C11 C10 H10 117.6 . . ?
C10 C11 C12 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 117.4(3) . . ?
C13 C12 C15 120.4(3) . . ?
C11 C12 C15 122.2(3) . . ?
C12 C13 C14 118.5(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
N2 C14 C13 124.5(3) . . ?
N2 C14 H14 117.8 . . ?
C13 C14 H14 117.8 . . ?
C15 C15 C12 179.0(4) 2_565 . ?
C17 C16 C18 119.3(3) . 2_666 ?
C17 C16 H16 120.3 . . ?
C18 C16 H16 120.3 2_666 . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 Br3 121.6(2) . . ?
C16 C17 Br3 117.8(2) . . ?
C17 C18 C16 120.1(2) . 2_666 ?
C17 C18 Br4 121.8(2) . . ?
C16 C18 Br4 118.0(2) 2_666 . ?

####################################################################### 
# 
# 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_diIBPA_250k
_database_code_depnum_ccdc_archive 'CCDC 1850147'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_date             2018-05-08T15:01:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H8 F4 I2 N2'
_chemical_formula_weight         582.06

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n n m'
_symmetry_space_group_name_Hall  '-P 2 2n'
_symmetry_Int_Tables_number      58
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, z'
'-x, -y, -z'
'x-1/2, -y-1/2, -z-1/2'
'-x-1/2, y-1/2, -z-1/2'
'x, y, -z'

_cell_length_a                   15.6860(7)
_cell_length_b                   5.2395(2)
_cell_length_c                   11.1083(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     912.96(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    256(2)
_cell_measurement_reflns_used    5963
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      31.47

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.067
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.7287
_shelx_estimated_absorpt_T_min   0.323
_shelx_estimated_absorpt_T_max   0.8

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      256(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_number            9763
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.247
_diffrn_reflns_theta_max         31.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             1591
_reflns_number_gt                1471
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0171P)²+0.3306P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1591
_refine_ls_number_parameters     67
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.02
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.0431
_refine_ls_wR_factor_gt          0.0422
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_restrained_S_all      1.12
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.083

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.15887(2) 0.97305(3) 0 0.03012(6) Uani 1 d . .
F1 F 0.06006(9) 0.6780(3) -0.21154(10) 0.0640(4) Uani 1 d . .
N1 N 0.71547(13) 0.6548(4) 0 0.0399(5) Uani 1 d . .
C5 C 0.59093(13) 0.2752(4) 0 0.0318(4) Uani 1 d . .
C2 C 0.03132(11) 0.5929(3) -0.10513(14) 0.0326(3) Uani 1 d . .
C1 C 0.06411(12) 0.6894(4) 0 0.0259(4) Uani 1 d . .
C4 C 0.62281(12) 0.3728(4) 0.10666(17) 0.0409(4) Uani 1 d . .
H4 H 0.6029 0.3132 0.1803 0.049 Uiso 1 calc . .
C3 C 0.68483(13) 0.5606(4) 0.1020(2) 0.0443(4) Uani 1 d . .
H3 H 0.7061 0.6241 0.1742 0.053 Uiso 1 calc . .
C6 C 0.52678(16) 0.0799(5) 0 0.0339(4) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.1019(19) . ?
F1 C2 1.3414(18) . ?
N1 C3 1.326(2) . ?
N1 C3 1.326(2) 8 ?
C5 C4 1.384(2) . ?
C5 C4 1.384(2) 8 ?
C5 C6 1.435(3) . ?
C2 C1 1.3726(19) . ?
C2 C2 1.383(3) 4_565 ?
C1 C2 1.3726(19) 8 ?
C4 C3 1.385(3) . ?
C4 H4 0.93 . ?
C3 H3 0.93 . ?
C6 C6 1.186(5) 5_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C3 117.4(2) . 8 ?
C4 C5 C4 117.8(2) . 8 ?
C4 C5 C6 121.12(10) . . ?
C4 C5 C6 121.12(10) 8 . ?
F1 C2 C1 120.08(14) . . ?
F1 C2 C2 118.22(8) . 4_565 ?
C1 C2 C2 121.70(9) . 4_565 ?
C2 C1 C2 116.60(18) 8 . ?
C2 C1 I1 121.70(9) 8 . ?
C2 C1 I1 121.70(9) . . ?
C5 C4 C3 118.98(17) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C3 C4 123.42(18) . . ?
N1 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C6 C6 C5 179.4(4) 5_655 . ?

####################################################################### 
# 
# 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_diIBPA_230k
_database_code_depnum_ccdc_archive 'CCDC 1850146'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_date             2018-05-08T15:00:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H8 F4 I2 N2'
_chemical_formula_weight         582.06

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n n m'
_symmetry_space_group_name_Hall  '-P 2 2n'
_symmetry_Int_Tables_number      58
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, z'
'-x, -y, -z'
'x-1/2, -y-1/2, -z-1/2'
'-x-1/2, y-1/2, -z-1/2'
'x, y, -z'

_cell_length_a                   15.6785(6)
_cell_length_b                   5.2396(2)
_cell_length_c                   11.0860(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     910.70(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    231(2)
_cell_measurement_reflns_used    6164
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      31.49

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.067
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.7287
_shelx_estimated_absorpt_T_min   0.322
_shelx_estimated_absorpt_T_max   0.8

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      231(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_number            9756
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         31.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             1589
_reflns_number_gt                1483
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0176P)²+0.3640P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1589
_refine_ls_number_parameters     67
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0191
_refine_ls_R_factor_gt           0.0174
_refine_ls_wR_factor_ref         0.0435
_refine_ls_wR_factor_gt          0.0428
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.09

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.15889(2) 0.97347(3) 0 0.02736(5) Uani 1 d . .
F1 F 0.06010(9) 0.6780(3) -0.21214(10) 0.0585(4) Uani 1 d . .
N1 N 0.28436(13) 0.3456(4) 0 0.0370(5) Uani 1 d . .
C5 C 0.40892(13) 0.7247(4) 0 0.0291(4) Uani 1 d . .
C2 C 0.03144(10) 0.5927(3) -0.10538(14) 0.0298(3) Uani 1 d . .
C1 C 0.06410(12) 0.6899(4) 0 0.0236(4) Uani 1 d . .
C4 C 0.37697(11) 0.6273(4) 0.10704(17) 0.0374(4) Uani 1 d . .
H4 H 0.3971 0.6879 0.1816 0.045 Uiso 1 calc . .
C3 C 0.31493(13) 0.4392(4) 0.1025(2) 0.0404(4) Uani 1 d . .
H3 H 0.2935 0.3747 0.1755 0.049 Uiso 1 calc . .
C6 C 0.47334(16) 0.9195(5) 0 0.0317(4) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.1015(19) . ?
F1 C2 1.3427(18) . ?
N1 C3 1.327(2) 8 ?
N1 C3 1.327(2) . ?
C5 C4 1.385(2) . ?
C5 C4 1.385(2) 8 ?
C5 C6 1.436(3) . ?
C2 C1 1.3735(18) . ?
C2 C2 1.384(3) 4_565 ?
C1 C2 1.3735(18) 8 ?
C4 C3 1.386(3) . ?
C4 H4 0.94 . ?
C3 H3 0.94 . ?
C6 C6 1.188(5) 5_675 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C3 117.8(2) 8 . ?
C4 C5 C4 117.9(2) . 8 ?
C4 C5 C6 121.07(10) . . ?
C4 C5 C6 121.07(10) 8 . ?
F1 C2 C1 120.09(13) . . ?
F1 C2 C2 118.18(8) . 4_565 ?
C1 C2 C2 121.73(9) . 4_565 ?
C2 C1 C2 116.54(18) . 8 ?
C2 C1 I1 121.73(9) . . ?
C2 C1 I1 121.73(9) 8 . ?
C5 C4 C3 118.97(17) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C3 C4 123.22(18) . . ?
N1 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C6 C6 C5 180.0(4) 5_675 . ?

####################################################################### 
# 
# 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_TBrB_BPA_230k
_database_code_depnum_ccdc_archive 'CCDC 1850151'
_audit_update_record             
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT341_TBrB_BPA_230k       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00717 Ang.  
RESPONSE: Due to weak high angle data.
;
_vrf_PLAT911_TBrB_BPA_230k       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
RESPONSE: These reflections were not collected.
;
_vrf_PLAT972_TBrB_BPA_230k       
;
PROBLEM: Check Calcd Resid. Dens.  0.90A   From Br2            -2.08 eA-3  
RESPONSE: Due to issues with the absorption correction.
;
_vrf_PLAT978_TBrB_BPA_230k       
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The residual electron density was around the halides.
;
# end Validation Reply Form

_audit_creation_date             2018-04-23T11:20:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H10 Br4 N2'
_chemical_formula_weight         573.92

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9472(3)
_cell_length_b                   13.2528(10)
_cell_length_c                   18.2138(15)
_cell_angle_alpha                72.838(2)
_cell_angle_beta                 85.776(2)
_cell_angle_gamma                83.982(2)
_cell_volume                     904.43(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    229(2)
_cell_measurement_reflns_used    4203
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.99

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.092
_exptl_crystal_density_diffrn    2.107
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.1256
_exptl_absorpt_correction_T_min  0.0679
_shelx_estimated_absorpt_T_min   0.095
_shelx_estimated_absorpt_T_max   0.495

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      229(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_number            10322
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.614
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_number_total             4483
_reflns_number_gt                3203
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0735P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4483
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.053
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.309
_refine_diff_density_min         -2.168
_refine_diff_density_rms         0.222

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.84149(14) 0.80566(4) 0.13730(3) 0.04299(17) Uani 1 d . .
Br2 Br 0.70634(15) 0.77201(4) -0.03386(4) 0.04634(18) Uani 1 d . .
Br3 Br 0.27404(13) 0.27814(4) 0.48138(3) 0.04069(16) Uani 1 d . .
Br4 Br 0.28962(14) 0.31632(4) 0.65597(3) 0.04208(16) Uani 1 d . .
N1 N 0.1191(13) -0.0390(4) 0.7689(3) 0.0484(12) Uani 1 d . .
N2 N 0.2592(12) 0.4531(4) 0.2646(3) 0.0443(11) Uani 1 d . .
C1 C 0.2626(15) -0.1107(4) 0.7362(3) 0.0493(14) Uani 1 d . .
H1 H 0.389959 -0.169912 0.767023 0.059 Uiso 1 calc . .
C2 C 0.2372(13) -0.1040(4) 0.6594(3) 0.0421(12) Uani 1 d . .
H2 H 0.343324 -0.15769 0.639254 0.051 Uiso 1 calc . .
C3 C 0.0526(12) -0.0170(4) 0.6127(3) 0.0367(11) Uani 1 d . .
C4 C -0.0990(13) 0.0590(4) 0.6468(3) 0.0410(12) Uani 1 d . .
H4 H -0.226685 0.119431 0.617474 0.049 Uiso 1 calc . .
C5 C -0.0600(13) 0.0447(4) 0.7235(3) 0.0421(13) Uani 1 d . .
H5 H -0.165092 0.096564 0.745477 0.051 Uiso 1 calc . .
C6 C 0.0192(13) -0.0057(4) 0.5332(3) 0.0411(12) Uani 1 d . .
C7 C 0.5616(11) 1.0141(3) 0.0703(3) 0.0312(10) Uani 1 d . .
H7 H 0.604831 1.023866 0.117674 0.037 Uiso 1 calc . .
C8 C 0.6458(11) 0.9169(3) 0.0572(3) 0.0287(10) Uani 1 d . .
C9 C 0.5875(11) 0.9028(4) -0.0129(3) 0.0311(10) Uani 1 d . .
C10 C 0.1242(14) 0.3781(4) 0.2426(3) 0.0444(13) Uani 1 d . .
H10 H 0.078697 0.31515 0.28086 0.053 Uiso 1 calc . .
C11 C 0.0482(13) 0.3862(4) 0.1690(3) 0.0382(12) Uani 1 d . .
H11 H -0.049086 0.330787 0.157992 0.046 Uiso 1 calc . .
C12 C 0.1161(12) 0.4768(4) 0.1109(3) 0.0325(10) Uani 1 d . .
C13 C 0.2613(13) 0.5571(4) 0.1314(3) 0.0375(11) Uani 1 d . .
H13 H 0.312051 0.620292 0.093975 0.045 Uiso 1 calc . .
C14 C 0.3266(14) 0.5405(4) 0.2074(3) 0.0455(14) Uani 1 d . .
H14 H 0.4254 0.594215 0.220337 0.055 Uiso 1 calc . .
C15 C 0.0340(12) 0.4929(4) 0.0325(3) 0.0356(11) Uani 1 d . .
C16 C 0.4925(11) 0.4851(4) 0.4275(3) 0.0326(11) Uani 1 d . .
H16 H 0.485983 0.474771 0.378691 0.039 Uiso 1 calc . .
C17 C 0.4029(11) 0.4061(3) 0.4934(3) 0.0295(10) Uani 1 d . .
C18 C 0.4091(11) 0.4215(4) 0.5656(3) 0.0299(10) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br1 C8 1.886(4) . ?
Br2 C9 1.888(4) . ?
Br3 C17 1.898(4) . ?
Br4 C18 1.882(5) . ?
N1 C1 1.323(7) . ?
N1 C5 1.339(7) . ?
N2 C14 1.345(7) . ?
N2 C10 1.346(7) . ?
C1 C2 1.386(8) . ?
C1 H1 0.94 . ?
C2 C3 1.386(7) . ?
C2 H2 0.94 . ?
C3 C4 1.394(7) . ?
C3 C6 1.426(7) . ?
C4 C5 1.371(7) . ?
C4 H4 0.94 . ?
C5 H5 0.94 . ?
C6 C6 1.193(10) 2_556 ?
C7 C8 1.381(6) . ?
C7 C9 1.389(6) 2_675 ?
C7 H7 0.94 . ?
C8 C9 1.382(6) . ?
C10 C11 1.366(7) . ?
C10 H10 0.94 . ?
C11 C12 1.381(7) . ?
C11 H11 0.94 . ?
C12 C13 1.412(6) . ?
C12 C15 1.438(7) . ?
C13 C14 1.377(7) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C15 1.188(10) 2_565 ?
C16 C18 1.379(6) 2_666 ?
C16 C17 1.391(7) . ?
C16 H16 0.94 . ?
C17 C18 1.391(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.5(5) . . ?
C14 N2 C10 115.0(5) . . ?
N1 C1 C2 124.2(5) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 118.8(5) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 117.2(5) . . ?
C2 C3 C6 121.3(5) . . ?
C4 C3 C6 121.5(5) . . ?
C5 C4 C3 119.4(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 123.8(5) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C6 C6 C3 177.8(8) 2_556 . ?
C8 C7 C9 119.5(4) . 2_675 ?
C8 C7 H7 120.3 . . ?
C9 C7 H7 120.3 2_675 . ?
C7 C8 C9 120.3(4) . . ?
C7 C8 Br1 118.0(3) . . ?
C9 C8 Br1 121.7(3) . . ?
C8 C9 C7 120.2(4) . 2_675 ?
C8 C9 Br2 121.7(4) . . ?
C7 C9 Br2 118.1(3) 2_675 . ?
N2 C10 C11 125.2(5) . . ?
N2 C10 H10 117.4 . . ?
C11 C10 H10 117.4 . . ?
C10 C11 C12 119.2(5) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 117.6(5) . . ?
C11 C12 C15 122.6(4) . . ?
C13 C12 C15 119.8(5) . . ?
C14 C13 C12 118.3(5) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
N2 C14 C13 124.7(5) . . ?
N2 C14 H14 117.6 . . ?
C13 C14 H14 117.6 . . ?
C15 C15 C12 179.4(7) 2_565 . ?
C18 C16 C17 119.3(4) 2_666 . ?
C18 C16 H16 120.3 2_666 . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.5(4) . . ?
C16 C17 Br3 117.9(3) . . ?
C18 C17 Br3 121.5(4) . . ?
C16 C18 C17 120.2(4) 2_666 . ?
C16 C18 Br4 118.2(4) 2_666 . ?
C17 C18 Br4 121.6(3) . . ?

