# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_Compound1Br2
_database_code_depnum_ccdc_archive 'CCDC 2212882'
loop_
_audit_author_name
_audit_author_address
'Nathan L. Kilah'
;University of Tasmania
Australia
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
_audit_creation_date             2020-05-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3

# start Validation Reply Form
_vrf_PLAT434_Compound1Br2        
;
PROBLEM: Short Inter HL..HL Contact Br1      ..Br2              3.20 Ang.  
RESPONSE: Halogen bond interaction.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 Br2 N4, 2(Br), 2[CH3OH]'
_chemical_formula_sum            'C11 H20 Br4 N4 O2'
_chemical_formula_weight         559.95
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   11.3746(5)
_cell_length_b                   12.0781(5)
_cell_length_c                   14.2650(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.327(2)
_cell_angle_gamma                90
_cell_volume                     1921.60(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7750
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      72.09
_cell_measurement_theta_min      4.84
_shelx_estimated_absorpt_T_max   0.532
_shelx_estimated_absorpt_T_min   0.232
_exptl_absorpt_coefficient_mu    10.304
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1041 before and 0.0721 after correction.
The Ratio of minimum to maximum transmission is 0.6316.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15824
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.323
_diffrn_reflns_theta_min         4.837
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  
'Bruker multilayer X-ray optics (Goebel mirror)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1636
_reflns_number_total             1891
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.897
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         1891
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+3.1823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0714
_refine_special_details          
;
The final refined structure uses a solvent mask. The observed void initially 
contained two difference peaks. The distance between these peaks suggested 
methanol. Attempts were made to model this region as methanol over two 
positions, however further difference peaks indicated more significant 
disorder beyond two positions. The thermal parameters were also poorly 
modelled. The mask process in Olex2 revealed a void and electron density 
corresponding to one methanol molecule per asymmetric unit (20 e-, 73 Α).  
The methanol has been included in the moiety and sum formula, which raises 
a number of general errors in checkCIF, but is considered appropriate based on 
the refinement process.
;

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H5A(0.5) H5B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.15468(3) 0.63024(3) 0.27459(3) 0.02443(12) Uani 1 1 d . . . . .
Br2 Br 0.51260(3) 0.66320(3) 0.30302(3) 0.02675(12) Uani 1 1 d . . . . .
N1 N 0.2850(3) 0.5026(2) 0.4266(2) 0.0242(6) Uani 1 1 d . . . . .
N2 N 0.3017(3) 0.4394(2) 0.2891(2) 0.0238(6) Uani 1 1 d . . . . .
C1 C 0.2518(3) 0.5165(3) 0.3326(3) 0.0216(7) Uani 1 1 d . . . . .
C2 C 0.3615(3) 0.4121(3) 0.4438(3) 0.0294(8) Uani 1 1 d . . . . .
H2 H 0.399050 0.383436 0.504280 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3717(3) 0.3735(3) 0.3582(3) 0.0288(8) Uani 1 1 d . . . . .
H3 H 0.418555 0.311750 0.346469 0.035 Uiso 1 1 calc R U . . .
C5 C 0.250000 0.5726(4) 0.500000 0.0369(13) Uani 1 2 d S T P . .
H5A H 0.182048 0.620588 0.470913 0.044 Uiso 0.5 1 calc R U P . .
H5B H 0.317953 0.620587 0.529087 0.044 Uiso 0.5 1 calc R U P . .
C4 C 0.2881(4) 0.4264(4) 0.1859(3) 0.0380(10) Uani 1 1 d . . . . .
H4A H 0.203124 0.416342 0.157393 0.057 Uiso 1 1 calc R U . . .
H4B H 0.333513 0.361436 0.172156 0.057 Uiso 1 1 calc R U . . .
H4C H 0.318549 0.492579 0.158888 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.852(3) . ?
N1 C1 1.332(5) . ?
N1 C2 1.389(5) . ?
N1 C5 1.460(4) . ?
N2 C1 1.309(4) . ?
N2 C3 1.390(4) . ?
N2 C4 1.458(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.333(6) . ?
C3 H3 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 108.7(3) . . ?
C1 N1 C5 125.9(3) . . ?
C2 N1 C5 125.4(3) . . ?
C1 N2 C3 108.3(3) . . ?
C1 N2 C4 125.8(3) . . ?
C3 N2 C4 125.9(3) . . ?
N1 C1 Br1 124.7(3) . . ?
N2 C1 Br1 126.3(3) . . ?
N2 C1 N1 108.9(3) . . ?
N1 C2 H2 126.9 . . ?
C3 C2 N1 106.2(3) . . ?
C3 C2 H2 126.9 . . ?
N2 C3 H3 126.0 . . ?
C2 C3 N2 107.9(3) . . ?
C2 C3 H3 126.0 . . ?
N1 C5 N1 109.3(4) . 2_556 ?
N1 C5 H5A 109.8 2_556 . ?
N1 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
N1 C5 H5B 109.8 2_556 . ?
H5A C5 H5B 108.3 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -0.2(4) . . . . ?
C1 N1 C2 C3 -0.3(4) . . . . ?
C1 N1 C5 N1 134.8(4) . . . 2_556 ?
C1 N2 C3 C2 0.6(4) . . . . ?
C2 N1 C1 Br1 -177.4(2) . . . . ?
C2 N1 C1 N2 0.6(4) . . . . ?
C2 N1 C5 N1 -47.2(3) . . . 2_556 ?
C3 N2 C1 Br1 177.2(2) . . . . ?
C3 N2 C1 N1 -0.8(4) . . . . ?
C5 N1 C1 Br1 0.9(5) . . . . ?
C5 N1 C1 N2 179.0(3) . . . . ?
C5 N1 C2 C3 -178.6(3) . . . . ?
C4 N2 C1 Br1 -1.7(5) . . . . ?
C4 N2 C1 N1 -179.7(3) . . . . ?
C4 N2 C3 C2 179.5(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.980 0.000 0.500 290.8 78.8 '4 CH3OH'
2 -0.191 0.500 0.000 290.8 78.8 '4 CH3OH'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'



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

data_Compound4PF62
_database_code_depnum_ccdc_archive 'CCDC 2212886'
loop_
_audit_author_name
_audit_author_address
'Nathan L. Kilah'
;University of Tasmania
Australia
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_Compound4PF62       
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: This error is unexpected as both measurement and ambient temperatures are reported in their relevant CIF entries. They are both 100(2)K.
;
_vrf_PLAT244_Compound4PF62       
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of         P2 Check
RESPONSE: No visible PF6 disorder.
;
_vrf_PLAT341_Compound4PF62       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0077 Ang.
RESPONSE: Data was collected at as high a resolution as available.
;
_vrf_PLAT431_Compound4PF62       
;
PROBLEM: Short Inter HL..A Contact  F1       ..N1       .       2.82 Ang.
RESPONSE: Possible weak imidazolium-PF6 interaction.
;
_vrf_PLAT906_Compound4PF62       
;
PROBLEM: Large K Value in the Analysis of Variance ......      4.981 Check
RESPONSE: The data collected was of relatively poor quality
;
_vrf_PLAT934_Compound4PF62       
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check
RESPONSE: Exclusion of outlier had a minimal influence on the refinement statistics.
;
_vrf_PLAT971_Compound4PF62       
;
PROBLEM: Check Calcd Resid. Dens.  0.99Ang From Br2             1.86 eA-3
RESPONSE: Residual density related to the heavy atom in the structure, and possibly an artifact of absorption correction.
;
_vrf_PLAT971_Compound4PF62_2     
;
PROBLEM: Check Calcd Resid. Dens.  0.93Ang From Br1             1.55 eA-3
RESPONSE: Residual density related to the heavy atom in the structure, and possibly an artifact of absorption correction.
;
_vrf_PLAT972_Compound4PF62       
;
PROBLEM: Check Calcd Resid. Dens.  0.56Ang From Br2            -1.74 eA-3
RESPONSE: Residual density related to the heavy atom in the structure, and possibly an artifact of absorption correction.
;
_vrf_PLAT972_Compound4PF62_2     
;
PROBLEM: Check Calcd Resid. Dens.  0.59Ang From Br2            -1.60 eA-3
RESPONSE: Residual density related to the heavy atom in the structure, and possibly an artifact of absorption correction.
;
_vrf_PLAT972_Compound4PF62_3     
;
PROBLEM: Check Calcd Resid. Dens.  0.51Ang From Br2            -1.54 eA-3
RESPONSE: Residual density related to the heavy atom in the structure, and possibly an artifact of absorption correction.
;
# Added during the CSD deposition process: Friday 14 October 2022 03:04 AM
# end Validation Reply Form

_audit_creation_date             2020-12-22
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 Br2 N4, 2(F6 P)'
_chemical_formula_sum            'C16 H18 Br2 F12 N4 P2'
_chemical_formula_weight         716.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H20 Br4 Cl2 P2 F12 N8'
_chemical_oxdiff_usercomment     AVW.101
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8622(10)
_cell_length_b                   13.5928(8)
_cell_length_c                   14.0750(11)
_cell_angle_alpha                90
_cell_angle_beta                 113.979(9)
_cell_angle_gamma                90
_cell_volume                     2423.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9279
_cell_measurement_temperature    100.04(10)
_cell_measurement_theta_max      31.9180
_cell_measurement_theta_min      2.1720
_shelx_estimated_absorpt_T_max   0.841
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    3.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.04261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.963
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            37152
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.227
_diffrn_reflns_theta_min         2.180
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.04(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -10.00 73.00 1.00 10.00 -- 8.20 57.00 60.00 83 2 ω 32.00 76.00 1.00 10.00 -- 8.20 19.00 120.00 44 3 ω -6.00 24.00 1.00 10.00 -- 8.20 19.00 120.00 30 4 ω -47.00 7.00 1.00 10.00 -- -9.76 -35.00 95.00 54 5 ω -20.00 64.00 1.00 10.00 -- -9.76 35.00-107.00 84 6 ω -39.00 27.00 1.00 10.00 -- 8.20 -19.00 -90.00 66 7 ω -64.00 -32.00 1.00 10.00 -- 8.20 -57.00 -60.00 32 8 ω -82.00 -57.00 1.00 10.00 -- -9.76 -35.00 95.00 25'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0495954000
_diffrn_orient_matrix_UB_12      0.0233982000
_diffrn_orient_matrix_UB_13      0.0138364000
_diffrn_orient_matrix_UB_21      -0.0059087000
_diffrn_orient_matrix_UB_22      -0.0025478000
_diffrn_orient_matrix_UB_23      -0.0524123000
_diffrn_orient_matrix_UB_31      -0.0252699000
_diffrn_orient_matrix_UB_32      0.0465841000
_diffrn_orient_matrix_UB_33      -0.0098357000
_diffrn_oxdiff_digest_frames     
;
01fa46acbfabe28f2565d17a17935166f3004183e11
;
_diffrn_oxdiff_digest_hkl        
;
0199492813e9651e90ffad9eeaba8266f68e91
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4898
_reflns_number_total             7978
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.086
_refine_diff_density_min         -1.685
_refine_diff_density_rms         0.220
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         7978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+18.3386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1656
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C10(H10), C9(H9), C11(H11), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.39382(4) 0.72941(4) 0.67104(4) 0.01955(12) Uani 1 1 d . . . . .
P2 P 0.23785(10) 0.85025(10) 0.82952(10) 0.0184(3) Uani 1 1 d . . . . .
P1 P 0.23354(9) 0.65860(9) 0.33446(10) 0.0163(2) Uani 1 1 d . . . . .
F3 F 0.2184(2) 0.7200(3) 0.2322(2) 0.0291(7) Uani 1 1 d . . . . .
F1 F 0.3590(2) 0.6668(3) 0.3726(3) 0.0297(7) Uani 1 1 d . . . . .
F5 F 0.2493(3) 0.5969(2) 0.4368(2) 0.0275(7) Uani 1 1 d . . . . .
F6 F 0.1082(2) 0.6506(2) 0.2959(3) 0.0264(7) Uani 1 1 d . . . . .
F4 F 0.2341(3) 0.5579(2) 0.2752(2) 0.0284(7) Uani 1 1 d . . . . .
F2 F 0.2323(3) 0.7592(2) 0.3943(3) 0.0288(7) Uani 1 1 d . . . . .
F7 F 0.3591(2) 0.8768(2) 0.8571(3) 0.0274(7) Uani 1 1 d . . . . .
F12 F 0.1166(3) 0.8241(3) 0.8016(3) 0.0343(8) Uani 1 1 d . . . . .
F9 F 0.2263(3) 0.8116(3) 0.7184(3) 0.0401(10) Uani 1 1 d . . . . .
F8 F 0.2041(3) 0.9580(3) 0.7822(3) 0.0374(9) Uani 1 1 d . . . . .
F11 F 0.2504(3) 0.8912(3) 0.9408(3) 0.0360(8) Uani 1 1 d . . . . .
F10 F 0.2731(3) 0.7438(3) 0.8776(3) 0.0442(10) Uani 1 1 d . . . . .
N1 N 0.5178(3) 0.7457(3) 0.5545(3) 0.0125(7) Uani 1 1 d . . . . .
N2 N 0.5320(3) 0.6023(3) 0.6268(3) 0.0187(8) Uani 1 1 d . . . . .
C1 C 0.4866(3) 0.6907(4) 0.6147(4) 0.0149(9) Uani 1 1 d . . . . .
C2 C 0.5845(3) 0.6900(4) 0.5249(4) 0.0156(9) Uani 1 1 d . . . . .
H2 H 0.616524 0.710161 0.481587 0.019 Uiso 1 1 calc R . . . .
C3 C 0.5945(4) 0.6014(4) 0.5704(4) 0.0195(10) Uani 1 1 d . . . . .
H3 H 0.635404 0.549206 0.565091 0.023 Uiso 1 1 calc R . . . .
C6 C 0.5364(4) 0.8936(3) 0.4599(4) 0.0154(9) Uani 1 1 d . . . . .
C7 C 0.4830(4) 0.8999(4) 0.3528(4) 0.0173(9) Uani 1 1 d . . . . .
H7 H 0.414147 0.876638 0.320860 0.021 Uiso 1 1 calc R . . . .
C8 C 0.5318(4) 0.9409(3) 0.2923(4) 0.0153(9) Uani 1 1 d . . . . .
C5 C 0.4838(4) 0.8490(4) 0.5248(4) 0.0182(9) Uani 1 1 d . . . . .
H5A H 0.500814 0.888029 0.587235 0.022 Uiso 1 1 calc R . . . .
H5B H 0.407788 0.850756 0.485835 0.022 Uiso 1 1 calc R . . . .
C10 C 0.6877(4) 0.9696(4) 0.4473(4) 0.0219(10) Uani 1 1 d . . . . .
H10 H 0.756070 0.994005 0.479248 0.026 Uiso 1 1 calc R . . . .
C9 C 0.6351(4) 0.9748(4) 0.3410(4) 0.0207(10) Uani 1 1 d . . . . .
H9 H 0.668657 1.001186 0.301527 0.025 Uiso 1 1 calc R . . . .
C12 C 0.4737(4) 0.9509(4) 0.1765(4) 0.0215(10) Uani 1 1 d . . . . .
H12A H 0.398648 0.943247 0.157891 0.026 Uiso 1 1 calc R . . . .
H12B H 0.485210 1.016433 0.155859 0.026 Uiso 1 1 calc R . . . .
C11 C 0.6400(4) 0.9281(4) 0.5080(4) 0.0174(9) Uani 1 1 d . . . . .
H11 H 0.676729 0.923488 0.579773 0.021 Uiso 1 1 calc R . . . .
C4 C 0.5199(5) 0.5207(4) 0.6901(5) 0.0330(13) Uani 1 1 d . . . . .
H4A H 0.566629 0.530719 0.761614 0.050 Uiso 1 1 calc GR . . . .
H4B H 0.536817 0.459726 0.666104 0.050 Uiso 1 1 calc GR . . . .
H4C H 0.448286 0.518659 0.683768 0.050 Uiso 1 1 calc GR . . . .
Br2 Br 0.37652(4) 0.72812(5) 0.13989(5) 0.02885(15) Uani 1 1 d . . . . .
N3 N 0.5080(3) 0.8774(3) 0.1189(3) 0.0184(8) Uani 1 1 d . . . . .
N4 N 0.5199(3) 0.7410(3) 0.0440(3) 0.0202(8) Uani 1 1 d . . . . .
C13 C 0.4730(3) 0.7850(4) 0.0986(4) 0.0173(9) Uani 1 1 d . . . . .
C14 C 0.5832(4) 0.8921(4) 0.0753(4) 0.0224(10) Uani 1 1 d . . . . .
H14 H 0.621421 0.949104 0.078162 0.027 Uiso 1 1 calc R . . . .
C16 C 0.5040(5) 0.6399(4) 0.0079(5) 0.0348(14) Uani 1 1 d . . . . .
H16A H 0.530308 0.596280 0.066522 0.052 Uiso 1 1 calc GR . . . .
H16B H 0.541162 0.628465 -0.035641 0.052 Uiso 1 1 calc GR . . . .
H16C H 0.430000 0.628160 -0.031157 0.052 Uiso 1 1 calc GR . . . .
C15 C 0.5878(4) 0.8079(4) 0.0298(4) 0.0206(10) Uani 1 1 d . . . . .
H15 H 0.630048 0.795836 -0.006094 0.025 Uiso 1 1 calc R . . . .


_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 1.840(4) . ?
P2 F7 1.604(3) . ?
P2 F12 1.602(3) . ?
P2 F9 1.594(4) . ?
P2 F8 1.598(4) . ?
P2 F11 1.604(3) . ?
P2 F10 1.588(4) . ?
P1 F3 1.601(3) . ?
P1 F1 1.602(3) . ?
P1 F5 1.603(3) . ?
P1 F6 1.600(3) . ?
P1 F4 1.605(3) . ?
P1 F2 1.609(3) . ?
N1 C1 1.328(6) . ?
N1 C2 1.383(6) . ?
N1 C5 1.487(6) . ?
N2 C1 1.335(6) . ?
N2 C3 1.393(6) . ?
N2 C4 1.474(7) . ?
C2 C3 1.344(7) . ?
C6 C7 1.385(7) . ?
C6 C5 1.509(6) . ?
C6 C11 1.396(7) . ?
C7 C8 1.401(7) . ?
C8 C9 1.390(7) . ?
C8 C12 1.502(7) . ?
C10 C9 1.374(7) . ?
C10 C11 1.394(7) . ?
C12 N3 1.482(6) . ?
Br2 C13 1.832(5) . ?
N3 C13 1.335(7) . ?
N3 C14 1.423(7) . ?
N4 C13 1.332(6) . ?
N4 C16 1.450(7) . ?
N4 C15 1.382(7) . ?
C14 C15 1.325(8) . ?

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
F12 P2 F7 179.8(2) . . ?
F12 P2 F11 90.20(19) . . ?
F9 P2 F7 89.38(19) . . ?
F9 P2 F12 90.52(19) . . ?
F9 P2 F8 89.8(2) . . ?
F9 P2 F11 178.8(2) . . ?
F8 P2 F7 89.73(19) . . ?
F8 P2 F12 90.1(2) . . ?
F8 P2 F11 89.2(2) . . ?
F11 P2 F7 89.90(19) . . ?
F10 P2 F7 89.5(2) . . ?
F10 P2 F12 90.7(2) . . ?
F10 P2 F9 90.5(2) . . ?
F10 P2 F8 179.1(2) . . ?
F10 P2 F11 90.4(2) . . ?
F3 P1 F1 89.62(18) . . ?
F3 P1 F5 179.7(2) . . ?
F3 P1 F4 90.21(19) . . ?
F3 P1 F2 90.12(19) . . ?
F1 P1 F5 90.15(19) . . ?
F1 P1 F4 89.96(18) . . ?
F1 P1 F2 90.38(18) . . ?
F5 P1 F4 89.62(18) . . ?
F5 P1 F2 90.04(18) . . ?
F6 P1 F3 90.15(17) . . ?
F6 P1 F1 179.8(2) . . ?
F6 P1 F5 90.08(18) . . ?
F6 P1 F4 90.01(18) . . ?
F6 P1 F2 89.66(18) . . ?
F4 P1 F2 179.5(2) . . ?
C1 N1 C2 108.4(4) . . ?
C1 N1 C5 124.2(4) . . ?
C2 N1 C5 127.4(4) . . ?
C1 N2 C3 107.8(4) . . ?
C1 N2 C4 126.2(4) . . ?
C3 N2 C4 126.0(4) . . ?
N1 C1 Br1 125.5(4) . . ?
N1 C1 N2 109.1(4) . . ?
N2 C1 Br1 125.3(4) . . ?
C3 C2 N1 107.4(4) . . ?
C2 C3 N2 107.2(4) . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 C11 119.8(4) . . ?
C11 C6 C5 119.7(4) . . ?
C6 C7 C8 120.6(5) . . ?
C7 C8 C12 121.1(4) . . ?
C9 C8 C7 119.1(5) . . ?
C9 C8 C12 119.7(4) . . ?
N1 C5 C6 111.9(4) . . ?
C9 C10 C11 120.9(5) . . ?
C10 C9 C8 120.3(5) . . ?
N3 C12 C8 112.5(4) . . ?
C10 C11 C6 119.2(5) . . ?
C13 N3 C12 125.6(4) . . ?
C13 N3 C14 107.8(4) . . ?
C14 N3 C12 126.5(4) . . ?
C13 N4 C16 126.0(5) . . ?
C13 N4 C15 108.0(4) . . ?
C15 N4 C16 126.0(5) . . ?
N3 C13 Br2 125.3(4) . . ?
N4 C13 Br2 125.7(4) . . ?
N4 C13 N3 109.0(4) . . ?
C15 C14 N3 105.9(4) . . ?
C14 C15 N4 109.2(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 15.482
_oxdiff_exptl_absorpt_empirical_full_min 0.445


####################################################################### 
# 
# 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_18cmt011
_database_code_depnum_ccdc_archive 'CCDC 2212891'
loop_
_audit_author_name
_audit_author_address
'Nathan Kilah'
;University of Tasmania
Australia
;
_audit_update_record             
;
2022-10-17 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
_audit_creation_date             2022-10-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;

# start Validation Reply Form
_vrf_PLAT911_18cmt011            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.596        100 Report
RESPONSE: The data collection used a strategy on a three circle instrument. 
The cause for the missing data is unknown.
;
_vrf_PLAT972_18cmt011            
;
PROBLEM: Check Calcd Resid. Dens.  0.74Ang From Br2            -1.52 eA-3  
RESPONSE: The 2-bromoimidazole showed residual disorder. Attempts were made 
to model the disorder over two sites of unequal occupancy, but these were 
unsuccessful.
;
# end Validation Reply Form


_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N2, C3 H3 Br N2'
_chemical_formula_sum            'C17 H15 Br N4'
_chemical_formula_weight         355.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.5070(14)
_cell_length_b                   10.372(3)
_cell_length_c                   19.916(3)
_cell_angle_alpha                89.231(18)
_cell_angle_beta                 82.220(11)
_cell_angle_gamma                82.968(18)
_cell_volume                     1524.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      66.66
_cell_measurement_theta_min      4.30
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.710
_exptl_absorpt_coefficient_mu    3.680
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0699 before and 0.0523 after correction.
The Ratio of minimum to maximum transmission is 0.9061.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34463
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        66.776
_diffrn_reflns_theta_max         66.776
_diffrn_reflns_theta_min         2.239
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4581
_reflns_number_total             5309
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0  (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.471
_refine_diff_density_min         -1.569
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+3.2454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1095
_refine_special_details          
'Rigid Body model used for distorted 2-bromoimidazole group. The disorder could not be modelled over two sites of unequal occupancy, but the residual electron density was distorting the five membered ring.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Free rotating group:
 C4(C6,C5,N4,N3)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C9(H9), C15(H15), C10(H10), C29(H29), C3(H3), C12(H12), C16(H16),
 C24(H24), C26(H26), C30(H30), C13(H13), C27(H27), C23(H23), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.50974(5) -0.23567(3) 0.28744(2) 0.02948(12) Uani 1 1 d . . . . .
N6 N 0.7617(3) 0.1543(2) 0.48995(13) 0.0183(5) Uani 1 1 d . . . . .
N5 N 0.8547(3) 0.3171(2) 0.58257(13) 0.0180(5) Uani 1 1 d . . . . .
N7 N 0.2462(4) 0.7608(2) 0.98647(13) 0.0213(6) Uani 1 1 d . . . . .
N8 N 0.1787(4) 0.9524(2) 0.89462(13) 0.0205(6) Uani 1 1 d . . . . .
N2 N 0.2469(4) -0.0569(3) 0.36370(16) 0.0267(6) Uani 1 1 d . . . . .
N1 N 0.3702(4) 0.0252(3) 0.26752(14) 0.0259(6) Uani 1 1 d . . . . .
C20 C 0.7895(4) 0.3710(3) 0.52705(15) 0.0166(6) Uani 1 1 d . . . . .
C19 C 0.7431(4) 0.2846(3) 0.47684(15) 0.0168(6) Uani 1 1 d . . . . .
C34 C 0.2550(4) 0.8846(3) 1.00471(15) 0.0193(6) Uani 1 1 d . . . . .
C14 C 0.6795(4) 0.3384(3) 0.41807(16) 0.0201(6) Uani 1 1 d . . . . .
C17 C 0.7160(4) 0.0756(3) 0.44485(16) 0.0212(7) Uani 1 1 d . . . . .
C8 C 0.8976(4) 0.3948(3) 0.62865(16) 0.0204(7) Uani 1 1 d . . . . .
C33 C 0.2162(4) 0.9871(3) 0.95648(15) 0.0181(6) Uani 1 1 d . . . . .
C1 C 0.3657(4) -0.0760(3) 0.30692(16) 0.0213(7) Uani 1 1 d . . . . .
C28 C 0.2200(4) 1.1174(3) 0.97504(17) 0.0229(7) Uani 1 1 d . . . . .
C11 C 0.7648(4) 0.5069(3) 0.51565(16) 0.0199(7) Uani 1 1 d . . . . .
C25 C 0.3010(4) 0.9183(3) 1.06809(16) 0.0241(7) Uani 1 1 d . . . . .
C2 C 0.2437(5) 0.1172(3) 0.30206(18) 0.0282(8) Uani 1 1 d . . . . .
H2A H 0.214437 0.203157 0.286535 0.034 Uiso 1 1 calc R U . . .
C9 C 0.8728(4) 0.5319(3) 0.62226(17) 0.0237(7) Uani 1 1 d . . . . .
H9 H 0.901739 0.585364 0.656591 0.028 Uiso 1 1 calc R U . . .
C15 C 0.6338(4) 0.2511(3) 0.37135(16) 0.0250(7) Uani 1 1 d . . . . .
H15 H 0.591250 0.282620 0.330684 0.030 Uiso 1 1 calc R U . . .
C10 C 0.8071(4) 0.5864(3) 0.56661(17) 0.0234(7) Uani 1 1 d . . . . .
H10 H 0.789828 0.678248 0.562135 0.028 Uiso 1 1 calc R U . . .
C29 C 0.1807(5) 1.2135(3) 0.92666(19) 0.0293(8) Uani 1 1 d . . . . .
H29 H 0.181833 1.302584 0.936921 0.035 Uiso 1 1 calc R U . . .
C22 C 0.2846(5) 0.6668(3) 1.03008(18) 0.0264(7) Uani 1 1 d . . . . .
C7 C 0.9740(5) 0.3320(3) 0.68834(17) 0.0282(7) Uani 1 1 d . . . . .
H7A H 0.876592 0.328507 0.726165 0.042 Uiso 1 1 calc R U . . .
H7B H 1.065315 0.382756 0.701792 0.042 Uiso 1 1 calc R U . . .
H7C H 1.030234 0.243653 0.676151 0.042 Uiso 1 1 calc R U . . .
C3 C 0.1674(5) 0.0691(3) 0.36056(17) 0.0270(7) Uani 1 1 d . . . . .
H3 H 0.077002 0.113341 0.393057 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6985(4) 0.5566(3) 0.45548(17) 0.0241(7) Uani 1 1 d . . . . .
H12 H 0.681577 0.647790 0.448471 0.029 Uiso 1 1 calc R U . . .
C16 C 0.6511(4) 0.1210(3) 0.38484(17) 0.0258(7) Uani 1 1 d . . . . .
H16 H 0.619470 0.061631 0.353848 0.031 Uiso 1 1 calc R U . . .
C24 C 0.3430(5) 0.8166(4) 1.11229(18) 0.0312(8) Uani 1 1 d . . . . .
H24 H 0.376738 0.834411 1.155183 0.037 Uiso 1 1 calc R U . . .
C31 C 0.1416(4) 1.0455(3) 0.85035(16) 0.0243(7) Uani 1 1 d . . . . .
C26 C 0.3050(5) 1.0517(3) 1.08455(17) 0.0289(8) Uani 1 1 d . . . . .
H26 H 0.335963 1.073654 1.127298 0.035 Uiso 1 1 calc R U . . .
C30 C 0.1414(5) 1.1786(3) 0.86543(18) 0.0287(8) Uani 1 1 d . . . . .
H30 H 0.113840 1.243091 0.832830 0.034 Uiso 1 1 calc R U . . .
C13 C 0.6593(4) 0.4763(3) 0.40842(17) 0.0248(7) Uani 1 1 d . . . . .
H13 H 0.617666 0.511630 0.368279 0.030 Uiso 1 1 calc R U . . .
C27 C 0.2652(5) 1.1468(3) 1.04001(18) 0.0305(8) Uani 1 1 d . . . . .
H27 H 0.267456 1.234765 1.052140 0.037 Uiso 1 1 calc R U . . .
C18 C 0.7374(5) -0.0679(3) 0.46019(18) 0.0295(8) Uani 1 1 d . . . . .
H18A H 0.866449 -0.101269 0.454599 0.044 Uiso 1 1 calc R U . . .
H18B H 0.676105 -0.113497 0.429003 0.044 Uiso 1 1 calc R U . . .
H18C H 0.683638 -0.082003 0.506938 0.044 Uiso 1 1 calc R U . . .
C23 C 0.3353(5) 0.6914(4) 1.09343(18) 0.0327(8) Uani 1 1 d . . . . .
H23 H 0.364108 0.621668 1.123018 0.039 Uiso 1 1 calc R U . . .
C21 C 0.2659(5) 0.5311(3) 1.0084(2) 0.0363(9) Uani 1 1 d . . . . .
H21A H 0.138657 0.515891 1.017823 0.054 Uiso 1 1 calc R U . . .
H21B H 0.339774 0.468258 1.033459 0.054 Uiso 1 1 calc R U . . .
H21C H 0.307119 0.520967 0.959684 0.054 Uiso 1 1 calc R U . . .
C32 C 0.0975(6) 1.0053(4) 0.78348(18) 0.0367(9) Uani 1 1 d . . . . .
H32A H -0.029605 1.035868 0.779783 0.055 Uiso 1 1 calc R U . . .
H32B H 0.117381 0.910330 0.779749 0.055 Uiso 1 1 calc R U . . .
H32C H 0.175645 1.043153 0.746992 0.055 Uiso 1 1 calc R U . . .
Br2 Br -0.02306(6) 0.59169(5) 0.82687(2) 0.05254(16) Uani 1 1 d . . . . .
H2 H 0.228(6) -0.107(4) 0.393(2) 0.039(13) Uiso 1 1 d . . . . .
C4 C 0.2255(2) 0.6019(2) 0.81103(11) 0.0282(8) Uani 1 1 d G . . . .
C6 C 0.4838(3) 0.6713(2) 0.81382(12) 0.0320(8) Uani 1 1 d G . . . .
H6 H 0.574574 0.722470 0.822859 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5118(2) 0.5587(2) 0.77718(12) 0.0347(9) Uani 1 1 d G . . . .
H5 H 0.625449 0.517620 0.756258 0.042 Uiso 1 1 calc R U . . .
N4 N 0.2991(3) 0.69808(18) 0.83560(11) 0.0301(7) Uani 1 1 d G . . . .
N3 N 0.3447(3) 0.51457(17) 0.77587(11) 0.0300(7) Uani 1 1 d G . . . .
H4 H 0.238(6) 0.761(5) 0.860(2) 0.053(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.878(3) . ?
N6 C19 1.367(4) . ?
N6 C17 1.328(4) . ?
N5 C20 1.356(4) . ?
N5 C8 1.326(4) . ?
N7 C34 1.352(4) . ?
N7 C22 1.328(4) . ?
N8 C33 1.363(4) . ?
N8 C31 1.329(4) . ?
N2 C1 1.343(4) . ?
N2 C3 1.374(5) . ?
N2 H2 0.79(5) . ?
N1 C1 1.303(4) . ?
N1 C2 1.380(4) . ?
C20 C19 1.456(4) . ?
C20 C11 1.419(4) . ?
C19 C14 1.406(4) . ?
C34 C33 1.452(5) . ?
C34 C25 1.412(4) . ?
C14 C15 1.410(5) . ?
C14 C13 1.434(5) . ?
C17 C16 1.405(5) . ?
C17 C18 1.509(5) . ?
C8 C9 1.418(5) . ?
C8 C7 1.496(5) . ?
C33 C28 1.410(4) . ?
C28 C29 1.410(5) . ?
C28 C27 1.428(5) . ?
C11 C10 1.409(5) . ?
C11 C12 1.425(5) . ?
C25 C24 1.399(5) . ?
C25 C26 1.431(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.344(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.362(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.366(5) . ?
C10 H10 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.357(5) . ?
C22 C23 1.402(5) . ?
C22 C21 1.506(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C3 H3 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.347(5) . ?
C16 H16 0.9500 . ?
C24 H24 0.9500 . ?
C24 C23 1.366(5) . ?
C31 C30 1.416(5) . ?
C31 C32 1.492(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.351(5) . ?
C30 H30 0.9500 . ?
C13 H13 0.9500 . ?
C27 H27 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C23 H23 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
Br2 C4 1.8658(17) . ?
C4 N4 1.3266 . ?
C4 N3 1.3269 . ?
C6 H6 0.9500 . ?
C6 C5 1.3650 . ?
C6 N4 1.3908 . ?
C5 H5 0.9500 . ?
C5 N3 1.3904 . ?
N4 H4 0.87(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N6 C19 117.8(3) . . ?
C8 N5 C20 118.7(3) . . ?
C22 N7 C34 118.2(3) . . ?
C31 N8 C33 118.5(3) . . ?
C1 N2 C3 105.7(3) . . ?
C1 N2 H2 127(3) . . ?
C3 N2 H2 127(3) . . ?
C1 N1 C2 103.3(3) . . ?
N5 C20 C19 118.1(3) . . ?
N5 C20 C11 123.2(3) . . ?
C11 C20 C19 118.7(3) . . ?
N6 C19 C20 117.8(3) . . ?
N6 C19 C14 123.2(3) . . ?
C14 C19 C20 119.0(3) . . ?
N7 C34 C33 118.1(3) . . ?
N7 C34 C25 123.0(3) . . ?
C25 C34 C33 118.9(3) . . ?
C19 C14 C15 117.0(3) . . ?
C19 C14 C13 120.2(3) . . ?
C15 C14 C13 122.8(3) . . ?
N6 C17 C16 122.7(3) . . ?
N6 C17 C18 117.1(3) . . ?
C16 C17 C18 120.2(3) . . ?
N5 C8 C9 121.9(3) . . ?
N5 C8 C7 117.3(3) . . ?
C9 C8 C7 120.8(3) . . ?
N8 C33 C34 118.1(3) . . ?
N8 C33 C28 122.8(3) . . ?
C28 C33 C34 119.1(3) . . ?
N2 C1 Br1 122.0(2) . . ?
N1 C1 Br1 124.0(2) . . ?
N1 C1 N2 114.0(3) . . ?
C33 C28 C29 117.1(3) . . ?
C33 C28 C27 119.9(3) . . ?
C29 C28 C27 122.9(3) . . ?
C20 C11 C12 120.1(3) . . ?
C10 C11 C20 116.5(3) . . ?
C10 C11 C12 123.4(3) . . ?
C34 C25 C26 120.1(3) . . ?
C24 C25 C34 117.2(3) . . ?
C24 C25 C26 122.7(3) . . ?
N1 C2 H2A 124.4 . . ?
C3 C2 N1 111.1(3) . . ?
C3 C2 H2A 124.4 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.1 . . ?
N7 C22 C23 122.5(3) . . ?
N7 C22 C21 116.0(3) . . ?
C23 C22 C21 121.4(3) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C3 H3 127.1 . . ?
C2 C3 N2 105.9(3) . . ?
C2 C3 H3 127.1 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 119.5 . . ?
C17 C16 H16 120.2 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C25 C24 H24 120.2 . . ?
C23 C24 C25 119.6(3) . . ?
C23 C24 H24 120.2 . . ?
N8 C31 C30 122.0(3) . . ?
N8 C31 C32 117.5(3) . . ?
C30 C31 C32 120.5(3) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.8(3) . . ?
C27 C26 H26 119.6 . . ?
C29 C30 C31 119.7(3) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.6 . . ?
C28 C27 H27 119.4 . . ?
C26 C27 C28 121.2(3) . . ?
C26 C27 H27 119.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.5(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N4 C4 Br2 122.06(12) . . ?
N4 C4 N3 113.9 . . ?
N3 C4 Br2 124.05(13) . . ?
C5 C6 H6 126.0 . . ?
C5 C6 N4 108.0 . . ?
N4 C6 H6 126.0 . . ?
C6 C5 H5 126.0 . . ?
C6 C5 N3 108.0 . . ?
N3 C5 H5 126.0 . . ?
C4 N4 C6 105.0 . . ?
C4 N4 H4 124(3) . . ?
C6 N4 H4 131(3) . . ?
C4 N3 C5 105.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N6 C19 C14 C15 0.0(4) . . . . ?
N6 C19 C14 C13 178.5(3) . . . . ?
N6 C17 C16 C15 0.1(5) . . . . ?
N5 C20 C19 N6 2.4(4) . . . . ?
N5 C20 C19 C14 -178.4(3) . . . . ?
N5 C20 C11 C10 -1.8(4) . . . . ?
N5 C20 C11 C12 178.9(3) . . . . ?
N5 C8 C9 C10 -1.6(5) . . . . ?
N7 C34 C33 N8 -2.1(4) . . . . ?
N7 C34 C33 C28 178.4(3) . . . . ?
N7 C34 C25 C24 1.7(5) . . . . ?
N7 C34 C25 C26 -179.0(3) . . . . ?
N7 C22 C23 C24 1.2(5) . . . . ?
N8 C33 C28 C29 0.7(5) . . . . ?
N8 C33 C28 C27 -178.2(3) . . . . ?
N8 C31 C30 C29 0.2(5) . . . . ?
N1 C2 C3 N2 0.0(4) . . . . ?
C20 N5 C8 C9 1.6(4) . . . . ?
C20 N5 C8 C7 -178.3(3) . . . . ?
C20 C19 C14 C15 -179.1(3) . . . . ?
C20 C19 C14 C13 -0.6(4) . . . . ?
C20 C11 C10 C9 1.8(4) . . . . ?
C20 C11 C12 C13 -0.5(5) . . . . ?
C19 N6 C17 C16 0.4(4) . . . . ?
C19 N6 C17 C18 -180.0(3) . . . . ?
C19 C20 C11 C10 178.3(3) . . . . ?
C19 C20 C11 C12 -0.9(4) . . . . ?
C19 C14 C15 C16 0.6(5) . . . . ?
C19 C14 C13 C12 -0.8(5) . . . . ?
C34 N7 C22 C23 -0.7(5) . . . . ?
C34 N7 C22 C21 177.8(3) . . . . ?
C34 C33 C28 C29 -179.8(3) . . . . ?
C34 C33 C28 C27 1.3(4) . . . . ?
C34 C25 C24 C23 -1.1(5) . . . . ?
C34 C25 C26 C27 0.0(5) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
C17 N6 C19 C20 178.7(3) . . . . ?
C17 N6 C19 C14 -0.5(4) . . . . ?
C8 N5 C20 C19 180.0(3) . . . . ?
C8 N5 C20 C11 0.1(4) . . . . ?
C8 C9 C10 C11 -0.2(5) . . . . ?
C33 N8 C31 C30 0.5(5) . . . . ?
C33 N8 C31 C32 -178.8(3) . . . . ?
C33 C34 C25 C24 -178.0(3) . . . . ?
C33 C34 C25 C26 1.3(5) . . . . ?
C33 C28 C29 C30 0.1(5) . . . . ?
C33 C28 C27 C26 0.0(5) . . . . ?
C1 N2 C3 C2 0.1(4) . . . . ?
C1 N1 C2 C3 -0.1(4) . . . . ?
C28 C29 C30 C31 -0.5(5) . . . . ?
C11 C20 C19 N6 -177.7(3) . . . . ?
C11 C20 C19 C14 1.5(4) . . . . ?
C11 C12 C13 C14 1.3(5) . . . . ?
C25 C34 C33 N8 177.6(3) . . . . ?
C25 C34 C33 C28 -1.9(4) . . . . ?
C25 C24 C23 C22 -0.3(5) . . . . ?
C25 C26 C27 C28 -0.7(5) . . . . ?
C2 N1 C1 Br1 179.9(2) . . . . ?
C2 N1 C1 N2 0.1(4) . . . . ?
C15 C14 C13 C12 177.6(3) . . . . ?
C10 C11 C12 C13 -179.7(3) . . . . ?
C29 C28 C27 C26 -178.9(3) . . . . ?
C22 N7 C34 C33 178.9(3) . . . . ?
C22 N7 C34 C25 -0.8(5) . . . . ?
C7 C8 C9 C10 178.4(3) . . . . ?
C3 N2 C1 Br1 -179.9(2) . . . . ?
C3 N2 C1 N1 -0.1(4) . . . . ?
C12 C11 C10 C9 -179.0(3) . . . . ?
C24 C25 C26 C27 179.3(3) . . . . ?
C31 N8 C33 C34 179.5(3) . . . . ?
C31 N8 C33 C28 -1.0(4) . . . . ?
C26 C25 C24 C23 179.6(3) . . . . ?
C13 C14 C15 C16 -177.9(3) . . . . ?
C27 C28 C29 C30 179.0(3) . . . . ?
C18 C17 C16 C15 -179.4(3) . . . . ?
C21 C22 C23 C24 -177.2(3) . . . . ?
C32 C31 C30 C29 179.6(3) . . . . ?
Br2 C4 N4 C6 179.4(2) . . . . ?
Br2 C4 N3 C5 -179.4(2) . . . . ?
C6 C5 N3 C4 0.3 . . . . ?
C5 C6 N4 C4 -0.3 . . . . ?
N4 C4 N3 C5 -0.5 . . . . ?
N4 C6 C5 N3 0.0 . . . . ?
N3 C4 N4 C6 0.6 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

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

data_Compound1BrPF6
_database_code_depnum_ccdc_archive 'CCDC 2212892'
loop_
_audit_author_name
_audit_author_address
'Nathan L. Kilah'
;University of Tasmania
Australia
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_Compound1BrPF6      
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: This error is unexpected as both mesurement and ambient temperatures are reported in their relevant CIF entries. They are both 100(2)K.
;
_vrf_PLAT434_Compound1BrPF6      
;
PROBLEM: Short Inter HL..HL Contact Br1      ..Br2      .       3.05 Ang.
RESPONSE: Halogen bonding interaction.
;
_vrf_RINTA01_Compound1BrPF6      
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: The crystals, though quite large, diffracted poorly on the synchrotron beamline. The data merged poorly.
;
_vrf_PLAT020_Compound1BrPF6      
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.129 Report
RESPONSE: The crystals, though quite large, diffracted poorly on the synchrotron beamline. The data merged poorly.
;
_vrf_PLAT084_Compound1BrPF6      
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.28 Report
RESPONSE: The crystals, though quite large, diffracted poorly on the synchrotron beamline. The merge was poor, and is reflected in the refinement statistics.
;
_vrf_PLAT341_Compound1BrPF6      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.015 Ang.
RESPONSE: The crystals, though quite large, diffracted poorly on the synchrotron beamline.
;
_vrf_PLAT790_Compound1BrPF6      
;
PROBLEM: Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
RESPONSE: The moieties have been selected to best show their interactions.
;
_vrf_PLAT905_Compound1BrPF6      
;
PROBLEM: Negative K value in the Analysis of Variance ...     -1.475 Report
RESPONSE: The crystals, though quite large, diffracted poorly on the synchrotron beamline. The data merged poorly.
;
_vrf_PLAT911_Compound1BrPF6      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         39 Report
RESPONSE: The crystals, though quite large, diffracted poorly on the synchrotron beamline. The data merged poorly.
;
_vrf_PLAT972_Compound1BrPF6      
;
PROBLEM: Check Calcd Resid. Dens.  0.51Ang From Br2            -1.98 eA-3
RESPONSE: The crystals, though quite large, diffracted poorly on the synchrotron beamline. The data merged poorly. Residual density may represent additional unmodelled disorder, or the poor merge.
;
_vrf_PLAT972_Compound1BrPF6_2    
;
PROBLEM: Check Calcd Resid. Dens.  0.41Ang From Br2            -1.57 eA-3
RESPONSE: The crystals, though quite large, diffracted poorly on the synchrotron beamline. The data merged poorly. Residual density may represent additional unmodelled disorder, or the poor merge.
;
# Added during the CSD deposition process: Friday 14 October 2022 03:06 AM
# end Validation Reply Form

_audit_creation_date             2022-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 Br2 N4, F6 P, Br [+ solvent]'
_chemical_formula_sum            'C9 H12 Br3 F6 N4 P [+ solvent]'
_chemical_formula_weight         560.93
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   6.9220(14)
_cell_length_b                   23.184(5)
_cell_length_c                   51.347(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8240(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    34488
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.582
_cell_measurement_theta_min      1.928
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.001
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4288
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1293
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       65
_diffrn_reflns_limit_l_min       -66
_diffrn_reflns_number            34488
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.582
_diffrn_reflns_theta_min         1.928
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'ADSC Quantum 210r'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1777
_reflns_number_total             2987
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.441
_refine_diff_density_min         -2.052
_refine_diff_density_rms         0.205
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0840
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1766P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2392
_refine_ls_wR_factor_ref         0.2753
_refine_special_details          'Solvent Masking in Olex2'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H5A(0.5) H5B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.27576(9) 0.46017(3) 0.58911(2) 0.0534(3) Uani 1 1 d . . . . .
Br2 Br 0.625000 0.47008(7) 0.625000 0.0906(5) Uani 1 2 d S T P . .
P1 P 0.375000 0.375000 0.50354(6) 0.0558(7) Uani 1 2 d S T P . .
F2 F 0.5938(7) 0.3537(2) 0.50424(12) 0.0820(15) Uani 1 1 d . . . . .
F3 F 0.4488(8) 0.4397(2) 0.50368(12) 0.0798(14) Uani 1 1 d . . . . .
F1 F 0.375000 0.375000 0.53461(14) 0.083(2) Uani 1 2 d S T P . .
F4 F 0.375000 0.375000 0.47337(17) 0.113(3) Uani 1 2 d S T P . .
N2 N -0.0975(8) 0.4257(4) 0.56651(13) 0.0685(17) Uani 1 1 d . . . . .
N1 N 0.0226(10) 0.4980(3) 0.54743(14) 0.0671(18) Uani 1 1 d . . . . .
C2 C 0.0513(11) 0.4605(4) 0.56547(18) 0.065(2) Uani 1 1 d . . . . .
C3 C -0.1600(14) 0.4867(5) 0.53684(19) 0.079(3) Uani 1 1 d . . . . .
H3 H -0.219089 0.508906 0.524018 0.094 Uiso 1 1 calc R . . . .
C4 C -0.2333(11) 0.4425(5) 0.5470(2) 0.082(3) Uani 1 1 d . . . . .
H4 H -0.349691 0.424780 0.542801 0.099 Uiso 1 1 calc R . . . .
C5 C -0.125000 0.375000 0.5839(2) 0.085(4) Uani 1 2 d S T P . .
H5A H -0.012636 0.369555 0.594882 0.102 Uiso 0.5 1 calc R . . . .
H5B H -0.237363 0.380446 0.594882 0.102 Uiso 0.5 1 calc R . . . .
C1 C 0.1644(17) 0.5433(4) 0.5381(2) 0.083(3) Uani 1 1 d . . . . .
H1A H 0.254124 0.551955 0.551827 0.124 Uiso 1 1 calc GR . . . .
H1B H 0.095499 0.577657 0.533383 0.124 Uiso 1 1 calc GR . . . .
H1C H 0.233400 0.528933 0.523257 0.124 Uiso 1 1 calc GR . . . .


_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 C2 1.972(8) . ?
P1 F2 1.593(5) 2 ?
P1 F2 1.593(5) . ?
P1 F3 1.586(5) . ?
P1 F3 1.586(5) 2 ?
P1 F1 1.595(8) . ?
P1 F4 1.549(9) . ?
N2 C2 1.310(10) . ?
N2 C4 1.428(12) . ?
N2 C5 1.487(10) . ?
N1 C2 1.286(11) . ?
N1 C3 1.401(11) . ?
N1 C1 1.514(12) . ?
C3 C4 1.257(15) . ?

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
F2 P1 F2 177.4(5) . 2 ?
F2 P1 F1 88.7(2) 2 . ?
F2 P1 F1 88.7(2) . . ?
F3 P1 F2 89.2(3) . . ?
F3 P1 F2 90.8(3) . 2 ?
F3 P1 F2 90.8(3) 2 . ?
F3 P1 F2 89.2(3) 2 2 ?
F3 P1 F3 179.5(5) . 2 ?
F3 P1 F1 89.7(2) 2 . ?
F3 P1 F1 89.7(2) . . ?
F4 P1 F2 91.3(2) . 2 ?
F4 P1 F2 91.3(2) . . ?
F4 P1 F3 90.3(2) . . ?
F4 P1 F3 90.3(2) . 2 ?
F4 P1 F1 180.0 . . ?
C2 N2 C4 108.7(8) . . ?
C2 N2 C5 127.8(6) . . ?
C4 N2 C5 123.5(7) . . ?
C2 N1 C3 107.0(8) . . ?
C2 N1 C1 126.6(7) . . ?
C3 N1 C1 126.3(8) . . ?
N2 C2 Br1 126.3(7) . . ?
N1 C2 Br1 124.6(6) . . ?
N1 C2 N2 109.0(7) . . ?
C4 C3 N1 110.8(9) . . ?
C3 C4 N2 104.4(8) . . ?
N2 C5 N2 106.4(9) 2_455 . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.989 0.125 0.125 233.1 67.6 ?
2 0.078 -0.125 0.875 233.1 70.5 ?
3 -0.280 0.125 0.625 233.1 67.6 ?
4 -0.731 0.375 0.375 233.1 70.5 ?
5 -0.174 0.375 0.875 233.1 70.5 ?
6 -0.989 0.625 0.625 233.1 67.6 ?
7 -0.280 0.625 0.125 233.1 67.6 ?
8 -0.174 0.875 0.375 233.1 70.5 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'

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

data_Compound6PF6
_database_code_depnum_ccdc_archive 'CCDC 2212887'
loop_
_audit_author_name
_audit_author_address
'Nathan L. Kilah'
;University of Tasmania
Australia
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
# Added during the CSD deposition process: Friday 14 October 2022 03:04 AM
# end Validation Reply Form

# start Validation Reply Form
_vrf_PLAT042_Compound6PF6        
;
PROBLEM: Calc. and Reported MoietyFormula Strings  Differ     Please Check
RESPONSE: Reported Moiety Formula more accurately reflects the observed structure.
;
_vrf_PLAT088_Compound6PF6        
;
PROBLEM: Poor Data / Parameter Ratio ....................       8.87 Note
RESPONSE: The structure is very disordered, necessitating the use of a large number of parameters in the refinement.
;
# Added during the CSD deposition process: Friday 14 October 2022 03:04 AM
# end Validation Reply Form

_audit_creation_date             2020-05-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C26 H26 Br4 N10), 2(F6 P)'
_chemical_formula_sum            'C13 H13 Br2 F12 N5 P2'
_chemical_formula_weight         689.04
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   22.4963(5)
_cell_length_b                   8.0607(2)
_cell_length_c                   11.9999(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2176.01(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9727
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      72.06
_cell_measurement_theta_min      3.93
_shelx_estimated_absorpt_T_max   0.671
_shelx_estimated_absorpt_T_min   0.265
_exptl_absorpt_coefficient_mu    7.239
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1174 before and 0.0677 after correction.
The Ratio of minimum to maximum transmission is 0.6221.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.103
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20218
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.220
_diffrn_reflns_theta_min         5.831
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  
'Bruker multilayer X-ray optics (Goebel mirror)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2003
_reflns_number_total             2142
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0  (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'enCIFer (Allen, 1997)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²+8.7135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1118
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C15-N13
 1.33 with sigma of 0.02
 N13-C5
 1.33 with sigma of 0.02
 C15-C16
 1.38 with sigma of 0.02
 C5-C6
 1.38 with sigma of 0.02
 C5-N11
 1.43 with sigma of 0.02
 C3-C2
 1.35 with sigma of 0.02
 C12-C13
 1.35 with sigma of 0.02
 N12-C11
 1.33 with sigma of 0.02
 N11-C11
 1.33 with sigma of 0.02
 N1-C1
 1.33 with sigma of 0.02
 N2-C1
 1.33 with sigma of 0.02
 C16-C7
 1.38 with sigma of 0.02
 C6-C7
 1.38 with sigma of 0.02
 C15-C16 \\sim C5-C6
 with sigma of 0.02
 C15-N13 \\sim N13-C5
 with sigma of 0.02
 C16-C7 \\sim C7-C6
 with sigma of 0.02
3. Rigid bond restraints
 N11, C12, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N1, C2, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N13, C7, C5, C6, C15, C16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N11 \\sim C12 \\sim C13: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
N1 \\sim C2 \\sim C3: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
5. Others
 Fixed Sof: Br1(0.5) Br11(0.5) N1(0.5) N2(0.5) N11(0.5) N12(0.5) N13(0.5)
 H7(0.5) C1(0.5) C2(0.5) H2(0.5) C3(0.5) H3(0.5) C4(0.5) H4A(0.5) H4B(0.5)
 H4C(0.5) C5(0.5) C6(0.5) H6(0.5) C11(0.5) C12(0.5) H12(0.5) C13(0.5) H13(0.5)
 C14(0.5) H14A(0.5) H14B(0.5) H14C(0.5) C15(0.5) C16(0.5) H16(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C3(H3), C6(H6), C12(H12), C13(H13), C16(H16)
6.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.68051(7) 0.6216(3) 0.21766(17) 0.0292(4) Uani 0.5 1 d . . P A -1
Br11 Br 0.45151(5) 0.31969(14) 0.45002(10) 0.0364(3) Uani 0.5 1 d . . P A -1
N1 N 0.5685(2) 0.5037(7) 0.1396(5) 0.0225(12) Uani 0.5 1 d D U P A -1
N2 N 0.6435(4) 0.3800(11) 0.0643(7) 0.0265(17) Uani 0.5 1 d D . P A -1
N11 N 0.3921(3) 0.5726(9) 0.3294(6) 0.0259(13) Uani 0.5 1 d D U P A -1
N12 N 0.3328(4) 0.3927(11) 0.4053(8) 0.0311(19) Uani 0.5 1 d D . P A -1
N13 N 0.4833(2) 0.5496(8) 0.2418(6) 0.0247(13) Uani 0.5 1 d D U P A -1
C7 C 0.500000 0.8889(6) 0.250000 0.0302(11) Uani 1 2 d DS TU P . .
H7 H 0.506056 1.005513 0.250839 0.036 Uiso 0.5 1 calc R U P A .
C1 C 0.6278(4) 0.4994(14) 0.1337(8) 0.0245(19) Uani 0.5 1 d D . P A -1
C2 C 0.5456(5) 0.3827(15) 0.0763(10) 0.039(3) Uani 0.5 1 d D U P A -1
H2 H 0.504708 0.356627 0.067518 0.046 Uiso 0.5 1 calc R U P A -1
C3 C 0.5942(3) 0.3013(10) 0.0252(6) 0.0290(15) Uani 0.5 1 d D U P A -1
H3 H 0.592721 0.211045 -0.025586 0.035 Uiso 0.5 1 calc R U P A -1
C4 C 0.7047(4) 0.3379(14) 0.0309(9) 0.039(2) Uani 0.5 1 d . . P A -1
H4A H 0.719493 0.421540 -0.021512 0.058 Uiso 0.5 1 calc R U P A -1
H4B H 0.705042 0.228711 -0.004967 0.058 Uiso 0.5 1 calc R U P A -1
H4C H 0.730306 0.335553 0.096972 0.058 Uiso 0.5 1 calc R U P A -1
C5 C 0.4452(4) 0.6516(11) 0.2895(7) 0.0234(18) Uani 0.5 1 d D U P A -1
C6 C 0.4499(8) 0.8207(14) 0.300(3) 0.023(3) Uani 0.5 1 d D U P A -1
H6 H 0.421286 0.885700 0.338620 0.028 Uiso 0.5 1 calc R U P A -1
C11 C 0.3882(4) 0.4351(13) 0.3901(8) 0.030(2) Uani 0.5 1 d D . P A -1
C12 C 0.3344(6) 0.622(3) 0.3020(15) 0.021(3) Uani 0.5 1 d D U P A -1
H12 H 0.323292 0.716748 0.260098 0.026 Uiso 0.5 1 calc R U P A -1
C13 C 0.2974(3) 0.5074(10) 0.3467(7) 0.0348(17) Uani 0.5 1 d D U P A -1
H13 H 0.255326 0.504968 0.339903 0.042 Uiso 0.5 1 calc R U P A -1
C14 C 0.3104(5) 0.2491(14) 0.4650(9) 0.046(2) Uani 0.5 1 d . . P A -1
H14A H 0.326032 0.147744 0.430725 0.069 Uiso 0.5 1 calc R U P A -1
H14B H 0.266897 0.247991 0.461727 0.069 Uiso 0.5 1 calc R U P A -1
H14C H 0.323248 0.254598 0.543002 0.069 Uiso 0.5 1 calc R U P A -1
C15 C 0.5310(4) 0.6157(11) 0.1979(7) 0.0226(18) Uani 0.5 1 d D U P A -1
C16 C 0.5412(9) 0.7853(13) 0.199(3) 0.026(3) Uani 0.5 1 d D U P A -1
H16 H 0.575793 0.830020 0.164461 0.031 Uiso 0.5 1 calc R U P A -1
P1 P 0.63908(5) 0.15518(13) 0.38064(9) 0.0338(3) Uani 1 1 d . . . . .
F1 F 0.61854(16) 0.3377(4) 0.4130(3) 0.0747(10) Uani 1 1 d . . . . .
F2 F 0.66809(13) 0.1332(4) 0.5012(2) 0.0640(9) Uani 1 1 d . . . . .
F3 F 0.57850(13) 0.0841(4) 0.4308(2) 0.0595(8) Uani 1 1 d . . . . .
F4 F 0.60839(13) 0.1767(4) 0.2632(2) 0.0532(7) Uani 1 1 d . . . . .
F5 F 0.69948(12) 0.2255(4) 0.3314(3) 0.0648(9) Uani 1 1 d . . . . .
F6 F 0.65759(16) -0.0286(4) 0.3485(2) 0.0683(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.841(11) . ?
Br11 C11 1.848(11) . ?
N1 C1 1.337(10) . ?
N1 C2 1.338(13) . ?
N1 C15 1.421(11) . ?
N2 C1 1.320(12) . ?
N2 C3 1.361(11) . ?
N2 C4 1.475(13) . ?
N11 C5 1.437(11) . ?
N11 C11 1.329(11) . ?
N11 C12 1.396(15) . ?
N12 C11 1.305(11) . ?
N12 C13 1.408(13) . ?
N12 C14 1.451(13) . ?
N13 C5 1.318(9) . ?
N13 C15 1.308(10) . ?
C7 H7 0.9500 3_655 ?
C7 H7 0.9500 . ?
C7 C6 1.391(10) . ?
C7 C16 1.392(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.414(12) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.373(11) . ?
C6 H6 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.353(16) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.386(11) . ?
C16 H16 0.9500 . ?
P1 F1 1.590(3) . ?
P1 F2 1.596(3) . ?
P1 F3 1.596(3) . ?
P1 F4 1.579(3) . ?
P1 F5 1.586(3) . ?
P1 F6 1.587(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 109.6(9) . . ?
C1 N1 C15 129.5(8) . . ?
C2 N1 C15 120.9(7) . . ?
C1 N2 C3 109.9(9) . . ?
C1 N2 C4 126.0(9) . . ?
C3 N2 C4 124.0(8) . . ?
C11 N11 C5 127.4(7) . . ?
C11 N11 C12 107.7(10) . . ?
C12 N11 C5 124.7(10) . . ?
C11 N12 C13 107.3(9) . . ?
C11 N12 C14 127.5(11) . . ?
C13 N12 C14 125.1(9) . . ?
C15 N13 C5 117.0(6) . . ?
C6 C7 H7 120.2 . . ?
C6 C7 H7 106.2(5) . 3_655 ?
C6 C7 C16 119.6(7) . . ?
C16 C7 H7 120.2 . . ?
C16 C7 H7 133.2(6) . 3_655 ?
N1 C1 Br1 126.8(8) . . ?
N2 C1 Br1 124.3(7) . . ?
N2 C1 N1 108.5(10) . . ?
N1 C2 H2 126.7 . . ?
N1 C2 C3 106.7(9) . . ?
C3 C2 H2 126.7 . . ?
N2 C3 C2 105.3(8) . . ?
N2 C3 H3 127.4 . . ?
C2 C3 H3 127.4 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N13 C5 N11 114.2(7) . . ?
N13 C5 C6 127.6(9) . . ?
C6 C5 N11 118.2(8) . . ?
C7 C6 H6 122.8 . . ?
C5 C6 C7 114.5(10) . . ?
C5 C6 H6 122.8 . . ?
N11 C11 Br11 125.6(7) . . ?
N12 C11 Br11 123.4(10) . . ?
N12 C11 N11 111.0(10) . . ?
N11 C12 H12 126.7 . . ?
C13 C12 N11 106.6(13) . . ?
C13 C12 H12 126.7 . . ?
N12 C13 H13 126.4 . . ?
C12 C13 N12 107.3(9) . . ?
C12 C13 H13 126.4 . . ?
N12 C14 H14A 109.5 . . ?
N12 C14 H14B 109.5 . . ?
N12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N13 C15 N1 115.3(7) . . ?
N13 C15 C16 122.4(9) . . ?
C16 C15 N1 122.1(8) . . ?
C7 C16 H16 120.5 . . ?
C15 C16 C7 118.9(9) . . ?
C15 C16 H16 120.5 . . ?
F1 P1 F2 90.0(2) . . ?
F1 P1 F3 89.52(19) . . ?
F3 P1 F2 88.12(16) . . ?
F4 P1 F1 89.39(19) . . ?
F4 P1 F2 178.20(17) . . ?
F4 P1 F3 90.18(15) . . ?
F4 P1 F5 90.17(16) . . ?
F4 P1 F6 90.00(16) . . ?
F5 P1 F1 90.52(19) . . ?
F5 P1 F2 91.54(17) . . ?
F5 P1 F3 179.65(18) . . ?
F5 P1 F6 91.05(19) . . ?
F6 P1 F1 178.3(2) . . ?
F6 P1 F2 90.53(17) . . ?
F6 P1 F3 88.91(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 1.1(11) . . . . ?
N1 C15 C16 C7 175.0(16) . . . . ?
N11 C5 C6 C7 -174.1(15) . . . . ?
N11 C12 C13 N12 2.4(16) . . . . ?
N13 C5 C6 C7 3(3) . . . . ?
N13 C15 C16 C7 1(3) . . . . ?
C1 N1 C2 C3 -1.9(11) . . . . ?
C1 N1 C15 N13 -143.0(8) . . . . ?
C1 N1 C15 C16 43(2) . . . . ?
C1 N2 C3 C2 0.1(11) . . . . ?
C2 N1 C1 Br1 -172.0(8) . . . . ?
C2 N1 C1 N2 2.0(10) . . . . ?
C2 N1 C15 N13 39.1(11) . . . . ?
C2 N1 C15 C16 -134.9(19) . . . . ?
C3 N2 C1 Br1 172.9(6) . . . . ?
C3 N2 C1 N1 -1.3(10) . . . . ?
C4 N2 C1 Br1 -8.3(14) . . . . ?
C4 N2 C1 N1 177.5(8) . . . . ?
C4 N2 C3 C2 -178.7(9) . . . . ?
C5 N11 C11 Br11 6.0(12) . . . . ?
C5 N11 C11 N12 -175.8(8) . . . . ?
C5 N11 C12 C13 174.1(9) . . . . ?
C5 N13 C15 N1 -175.2(7) . . . . ?
C5 N13 C15 C16 -1(2) . . . . ?
C6 C7 C16 C15 1(5) . . . . ?
C11 N11 C5 N13 47.8(11) . . . . ?
C11 N11 C5 C6 -135.0(18) . . . . ?
C11 N11 C12 C13 -1.1(16) . . . . ?
C11 N12 C13 C12 -2.9(13) . . . . ?
C12 N11 C5 N13 -126.4(13) . . . . ?
C12 N11 C5 C6 51(2) . . . . ?
C12 N11 C11 Br11 -179.1(10) . . . . ?
C12 N11 C11 N12 -0.8(13) . . . . ?
C13 N12 C11 Br11 -179.4(6) . . . . ?
C13 N12 C11 N11 2.3(10) . . . . ?
C14 N12 C11 Br11 -3.0(14) . . . . ?
C14 N12 C11 N11 178.8(9) . . . . ?
C14 N12 C13 C12 -179.5(13) . . . . ?
C15 N1 C1 Br1 9.9(12) . . . . ?
C15 N1 C1 N2 -176.1(8) . . . . ?
C15 N1 C2 C3 176.4(7) . . . . ?
C15 N13 C5 N11 176.0(7) . . . . ?
C15 N13 C5 C6 -1(2) . . . . ?
C16 C7 C6 C5 -2(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'




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

data_Compound3PF62
_database_code_depnum_ccdc_archive 'CCDC 2212884'
loop_
_audit_author_name
_audit_author_address
'Nathan L. Kilah'
;University of Tasmania
Australia
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT220_Compound3PF62       
;
PROBLEM: NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range       10.0 Ratio
RESPONSE: The structure contains significant disorder and required significant numbers of restraints to give a resonable structural refinement. When contrasted with the more orderered regions, the value of Ueq(max)/Ueq(min) is predictably poor.
;
_vrf_PLAT220_Compound3PF62_2     
;
PROBLEM: NonSolvent   Resd 1  N   Ueq(max)/Ueq(min) Range        3.3 Ratio
RESPONSE: The structure contains significant disorder and required significant numbers of restraints to give a resonable structural refinement. When contrasted with the more orderered regions, the value of Uiso(max)/Uiso(min) is predictably poor.
;
_vrf_PLAT222_Compound3PF62       
;
PROBLEM: NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        7.9 Ratio
RESPONSE: The structure contains significant disorder and required significant numbers of restraints to give a resonable structural refinement. When contrasted with the more orderered regions, the value of Uiso(max)/Uiso(min) is predictably poor.
;
_vrf_PLAT250_Compound3PF62       
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note
RESPONSE: The structure contains significant disorder and required significant numbers of restraints to give a resonable structural refinement. When contrasted with the more orderered regions, the value of U3/U1 is predictably poor.
;
# Added during the CSD deposition process: Friday 14 October 2022 03:03 AM
# end Validation Reply Form

_audit_creation_date             2020-05-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H30 Br2 N4, 2(F6 P)'
_chemical_formula_sum            'C26 H30 Br2 F12 N4 P2'
_chemical_formula_weight         848.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.9048(3)
_cell_length_b                   30.2448(12)
_cell_length_c                   13.5305(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.882(2)
_cell_angle_gamma                90
_cell_volume                     3186.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      66.79
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.069
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0602 after correction.
The Ratio of minimum to maximum transmission is 0.8500.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26503
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.821
_diffrn_reflns_theta_max         66.821
_diffrn_reflns_theta_min         2.922
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  
'Bruker multilayer X-ray optics (Goebel mirror)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4897
_reflns_number_total             5597
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         5597
_refine_ls_number_restraints     193
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+7.0906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0976
_refine_special_details          
;
The structure solution showed the main residue was disordered. A region of 
electron density was observed near carbons C16 and C17 indicating disorder 
of the bromoimidazolium unit. The disorder was modelled as two parts of 
unequal occupancy. This gave a satisfactory model for the imidazolium ring, 
but the mesityl ring (which could not be coincident with the initial 
refinement based on geometric considerations) was not well modelled by 
anisotropic thermal paramaters (even with the use of extensive restraints. 
Therefore the atoms of the minor component of the mesityl group were included 
with isotropic thermal parameters. A large number of restraints were required 
to keep the thermal parameters and bond lenghts and angles physically 
reasonable.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N4A-Br2A
 2.82 with sigma of 0.04
 N3A-Br2A
 2.82 with sigma of 0.04
 C23-C22 \\sim C19A-C20A
 with sigma of 0.02
 C23-C18 \\sim C19A-C18A
 with sigma of 0.02
 C23-C26 \\sim C19A-C24A
 with sigma of 0.02
 C22-C21 \\sim C20A-C21A
 with sigma of 0.02
 C18-C19 \\sim C18A-C23A
 with sigma of 0.02
 C18-N4 \\sim C18A-N4A
 with sigma of 0.02
 C14-N3 \\sim C14-N3A
 with sigma of 0.02
 C21-C20 \\sim C21A-C20A
 with sigma of 0.02
 C21-C25 \\sim C21A-C25A
 with sigma of 0.02
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 C19-C24 \\sim C19A-C24A
 with sigma of 0.02
 Br2-C15 \\sim Br2A-C15A
 with sigma of 0.02
 N4-C16 \\sim N4A-C16A
 with sigma of 0.02
 N4-C15 \\sim N4A-C15A
 with sigma of 0.02
 C17-C16 \\sim C17A-C16A
 with sigma of 0.02
 C17-N3 \\sim C17A-N3A
 with sigma of 0.02
 N3-C15 \\sim N3A-C15A
 with sigma of 0.02
 C23-C21 \\sim C23A-C21A
 with sigma of 0.04
 C23-C19 \\sim C23A-C19A
 with sigma of 0.04
 C23-N4 \\sim C23A-N4A
 with sigma of 0.04
 C22-C18 \\sim C22A-C18A
 with sigma of 0.04
 C22-C20 \\sim C22A-C20A
 with sigma of 0.04
 C22-C25 \\sim C22A-C25A
 with sigma of 0.04
 C22-C26 \\sim C22A-C26A
 with sigma of 0.04
 C18-C20 \\sim C18A-C20A
 with sigma of 0.04
 C18-C26 \\sim C18A-C26A
 with sigma of 0.04
 C18-C24 \\sim C18A-C24A
 with sigma of 0.04
 C18-C16 \\sim C18A-C16A
 with sigma of 0.04
 C18-C15 \\sim C18A-C15A
 with sigma of 0.04
 C14-C17 \\sim C14-C17A
 with sigma of 0.04
 C14-C15 \\sim C14-C15A
 with sigma of 0.04
 C21-C19 \\sim C21A-C19A
 with sigma of 0.04
 C19-N4 \\sim C19A-N4A
 with sigma of 0.04
 C20-C25 \\sim C20A-C25A
 with sigma of 0.04
 C20-C24 \\sim C20A-C24A
 with sigma of 0.04
 Br2-N4 \\sim Br2A-N4A
 with sigma of 0.04
 Br2-N3 \\sim Br2A-N3A
 with sigma of 0.04
 N4-C17 \\sim N4A-C17A
 with sigma of 0.04
 N4-N3 \\sim N4A-N3A
 with sigma of 0.04
 C17-C15 \\sim C17A-C15A
 with sigma of 0.04
 C16-N3 \\sim C16A-N3A
 with sigma of 0.04
 C16-C15 \\sim C16A-C15A
 with sigma of 0.04
 C13-C14 \\sim C13-C14A
 with sigma of 0.02
 C14-N3 \\sim C14A-N3A
 with sigma of 0.02
 N3A-C14A \\sim C14-N3
 with sigma of 0.02
 C14-C13 \\sim C14A-C13
 with sigma of 0.02
3. Restrained planarity
 Br2, N3, N4, C14, C15, C16, C17, C18
 with sigma of 0.1
 Br2A, N3A, N4A, C14A, C15A, C16A, C17A, C18A
 with sigma of 0.1
 N4, C18, C19, C20, C21, C22, C23, C24, C25, C26
 with sigma of 0.1
 N4A, C18A, C19A, C20A, C21A, C22A, C23A, C24A, C25A, C26A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C15A \\sim N3A \\sim C17A \\sim C16A \\sim N4A: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 1.7A
C18A \\sim C24A \\sim C19A \\sim C23A \\sim C26A \\sim C22A \\sim C21A \\sim
C20A \\sim C25A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 1.7A
C15A \\sim N3A \\sim C17A \\sim C16A \\sim N4A \\sim Br2A \\sim C24A \\sim C19A
\\sim C20A \\sim C21A \\sim C25A \\sim C22A \\sim C23A \\sim C18A \\sim C26A:
within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
Uanis(Br2A) \\sim Ueq, Uanis(N3A) \\sim Ueq, Uanis(N4A) \\sim Ueq, Uanis(C14A)
\\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C17A) \\sim Ueq,
: with sigma of 0.01 and sigma for terminal atoms of 0.02
: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 N3A, C15A, N4A, C16A, C17A, Br2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H13C)=Sof(H13D)=Sof(Br2A)=Sof(N3A)=Sof(N4A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=
 Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(C23A)=
 Sof(C22A)=Sof(H22A)=Sof(C21A)=Sof(C20A)=Sof(H20A)=Sof(C19A)=Sof(C26A)=
 Sof(H26D)=Sof(H26E)=Sof(H26F)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=
 Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(H13A)=Sof(H13B)=Sof(Br2)=Sof(N3)=Sof(N4)=Sof(C14)=Sof(H14A)=Sof(H14B)=
 Sof(C15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(C19)=Sof(C20)=
 Sof(H20)=Sof(C21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(C24)=Sof(H24A)=Sof(H24B)=
 Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C26)=Sof(H26A)=Sof(H26B)=
 Sof(H26C)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13(H13C,H13D), C14(H14A,H14B), C14A(H14C,H14D)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C16(H16), C17(H17), C20(H20), C22(H22),
 C16A(H16A), C17A(H17A), C22A(H22A), C20A(H20A)
7.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C26A(H26D,H26E,H26F),
 C25A(H25D,H25E,H25F), C24A(H24D,H24E,H24F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.32224(5) 0.63559(2) 0.70077(3) 0.03281(13) Uani 1 1 d . . . . .
N1 N 0.4308(3) 0.66655(9) 0.5246(2) 0.0227(6) Uani 1 1 d . . . . .
N2 N 0.5022(4) 0.59837(9) 0.5585(2) 0.0225(6) Uani 1 1 d . . . . .
C1 C 0.4229(4) 0.63338(11) 0.5883(2) 0.0215(7) Uani 1 1 d . . . . .
C2 C 0.5190(5) 0.65213(12) 0.4513(3) 0.0271(7) Uani 1 1 d . . . . .
H2 H 0.543639 0.668940 0.396209 0.033 Uiso 1 1 calc R U . . .
C3 C 0.5637(5) 0.60988(12) 0.4723(3) 0.0294(8) Uani 1 1 d . . . . .
H3 H 0.626183 0.591314 0.434849 0.035 Uiso 1 1 calc R U . . .
C4 C 0.5314(4) 0.55676(11) 0.6126(2) 0.0222(7) Uani 1 1 d . . . . .
C5 C 0.3945(4) 0.52761(11) 0.6097(2) 0.0227(7) Uani 1 1 d . . . . .
C6 C 0.4235(5) 0.48968(11) 0.6688(2) 0.0253(7) Uani 1 1 d . . . . .
H6 H 0.331438 0.469660 0.670564 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5836(5) 0.48044(11) 0.7251(3) 0.0258(7) Uani 1 1 d . . . . .
C8 C 0.7172(5) 0.50935(12) 0.7214(3) 0.0283(8) Uani 1 1 d . . . . .
H8 H 0.827953 0.502280 0.757326 0.034 Uiso 1 1 calc R U . . .
C9 C 0.6951(4) 0.54881(11) 0.6665(3) 0.0253(7) Uani 1 1 d . . . . .
C10 C 0.2230(5) 0.53535(13) 0.5444(3) 0.0329(8) Uani 1 1 d . . . . .
H10A H 0.180571 0.564772 0.558092 0.049 Uiso 1 1 calc R U . . .
H10B H 0.141332 0.512873 0.558744 0.049 Uiso 1 1 calc R U . . .
H10C H 0.235547 0.533453 0.473677 0.049 Uiso 1 1 calc R U . . .
C11 C 0.6083(5) 0.43961(13) 0.7908(3) 0.0374(9) Uani 1 1 d . . . . .
H11A H 0.546567 0.443294 0.847211 0.056 Uiso 1 1 calc R U . . .
H11B H 0.730878 0.435406 0.816444 0.056 Uiso 1 1 calc R U . . .
H11C H 0.563321 0.413707 0.751309 0.056 Uiso 1 1 calc R U . . .
C12 C 0.8431(5) 0.58047(14) 0.6674(3) 0.0381(9) Uani 1 1 d . . . . .
H12A H 0.878366 0.580441 0.601404 0.057 Uiso 1 1 calc R U . . .
H12B H 0.939798 0.571181 0.718517 0.057 Uiso 1 1 calc R U . . .
H12C H 0.807114 0.610326 0.682832 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3803(4) 0.71254(11) 0.5392(3) 0.0282(8) Uani 1 1 d D . . . .
H13A H 0.436244 0.732143 0.495814 0.034 Uiso 0.9227(19) 1 calc R U P A 1
H13B H 0.421368 0.721211 0.609760 0.034 Uiso 0.9227(19) 1 calc R U P A 1
H13C H 0.401810 0.730734 0.481772 0.034 Uiso 0.0773(19) 1 calc R U P A 2
H13D H 0.450769 0.724548 0.600897 0.034 Uiso 0.0773(19) 1 calc R U P A 2
Br2 Br -0.14153(5) 0.76992(2) 0.38141(3) 0.02625(14) Uani 0.9227(19) 1 d D . P
A 1
N3 N 0.1501(4) 0.76535(9) 0.5356(2) 0.0194(6) Uani 0.9227(19) 1 d D . P A 1
N4 N 0.0292(3) 0.83011(9) 0.5231(2) 0.0178(6) Uani 0.9227(19) 1 d D . P A 1
C14 C 0.1867(5) 0.71892(16) 0.5145(4) 0.0253(10) Uani 0.9227(19) 1 d D . P A 1
H14A H 0.144537 0.712075 0.442978 0.030 Uiso 0.9227(19) 1 calc R U P A 1
H14B H 0.128642 0.698977 0.556105 0.030 Uiso 0.9227(19) 1 calc R U P A 1
C15 C 0.0246(4) 0.78959(11) 0.4837(3) 0.0193(7) Uani 0.9227(19) 1 d D . P A 1
C16 C 0.1613(7) 0.83173(19) 0.6035(4) 0.0252(12) Uani 0.9227(19) 1 d D . P A 1
H16 H 0.194094 0.856610 0.645228 0.030 Uiso 0.9227(19) 1 calc R U P A 1
C17 C 0.2371(5) 0.79083(16) 0.6123(3) 0.0251(9) Uani 0.9227(19) 1 d D . P A 1
H17 H 0.331237 0.781830 0.661592 0.030 Uiso 0.9227(19) 1 calc R U P A 1
C18 C -0.0689(5) 0.86924(11) 0.4857(3) 0.0187(7) Uani 0.9227(19) 1 d D . P A 1
C19 C -0.2367(6) 0.87423(18) 0.4987(5) 0.0268(15) Uani 0.9227(19) 1 d D . P A 1
C20 C -0.3176(8) 0.91373(18) 0.4639(6) 0.0309(16) Uani 0.9227(19) 1 d D . P A 1
H20 H -0.434910 0.917760 0.469054 0.037 Uiso 0.9227(19) 1 calc R U P A 1
C21 C -0.2333(6) 0.94718(14) 0.4222(4) 0.0266(12) Uani 0.9227(19) 1 d D . P A 1
C22 C -0.0641(7) 0.94024(16) 0.4098(5) 0.0266(14) Uani 0.9227(19) 1 d D . P A 1
H22 H -0.006164 0.962578 0.379223 0.032 Uiso 0.9227(19) 1 calc R U P A 1
C23 C 0.0216(6) 0.90139(15) 0.4413(3) 0.0219(10) Uani 0.9227(19) 1 d D . P A 1
C24 C -0.3293(9) 0.8401(2) 0.5509(6) 0.0417(16) Uani 0.9227(19) 1 d D . P A 1
H24A H -0.405154 0.822638 0.500668 0.063 Uiso 0.9227(19) 1 calc R U P A 1
H24B H -0.397717 0.854987 0.594912 0.063 Uiso 0.9227(19) 1 calc R U P A 1
H24C H -0.245273 0.820575 0.590862 0.063 Uiso 0.9227(19) 1 calc R U P A 1
C25 C -0.3206(6) 0.99062(15) 0.3923(4) 0.0398(11) Uani 0.9227(19) 1 d D . P A 1
H25A H -0.340231 0.993464 0.319102 0.060 Uiso 0.9227(19) 1 calc R U P A 1
H25B H -0.247501 1.014956 0.422383 0.060 Uiso 0.9227(19) 1 calc R U P A 1
H25C H -0.430894 0.991702 0.416082 0.060 Uiso 0.9227(19) 1 calc R U P A 1
C26 C 0.2042(6) 0.89478(18) 0.4263(5) 0.0358(12) Uani 0.9227(19) 1 d D . P A 1
H26A H 0.279609 0.893229 0.491753 0.054 Uiso 0.9227(19) 1 calc R U P A 1
H26B H 0.239025 0.919616 0.387861 0.054 Uiso 0.9227(19) 1 calc R U P A 1
H26C H 0.212760 0.867174 0.389569 0.054 Uiso 0.9227(19) 1 calc R U P A 1
Br2A Br 0.2025(11) 0.8182(4) 0.6326(6) 0.045(3) Uani 0.0773(19) 1 d D U P A 2
N3A N 0.077(3) 0.7507(8) 0.498(2) 0.058(9) Uani 0.0773(19) 1 d D U P A 2
N4A N -0.045(3) 0.8158(8) 0.4627(16) 0.051(8) Uani 0.0773(19) 1 d D U P A 2
C14A C 0.188(3) 0.7152(16) 0.548(4) 0.019(16) Uani 0.0773(19) 1 d D U P A 2
H14C H 0.135497 0.686776 0.522853 0.022 Uiso 0.0773(19) 1 calc R U P A 2
H14D H 0.182546 0.716633 0.620318 0.022 Uiso 0.0773(19) 1 calc R U P A 2
C15A C 0.070(3) 0.7929(9) 0.5238(15) 0.058(10) Uani 0.0773(19) 1 d D U P A 2
C16A C -0.118(4) 0.7858(11) 0.391(2) 0.059(10) Uani 0.0773(19) 1 d D U P A 2
H16A H -0.205832 0.792229 0.335453 0.071 Uiso 0.0773(19) 1 calc R U P A 2
C17A C -0.044(4) 0.7452(11) 0.413(2) 0.057(9) Uani 0.0773(19) 1 d D U P A 2
H17A H -0.071135 0.718509 0.376260 0.069 Uiso 0.0773(19) 1 calc R U P A 2
C18A C -0.102(3) 0.8620(8) 0.4565(15) 0.002(8) Uiso 0.0773(19) 1 d D U P A 2
C23A C -0.257(5) 0.8691(14) 0.488(4) 0.008(12) Uiso 0.0773(19) 1 d D U P A 2
C22A C -0.323(7) 0.9133(14) 0.483(5) 0.007(12) Uiso 0.0773(19) 1 d D U P A 2
H22A H -0.428702 0.919302 0.504490 0.009 Uiso 0.0773(19) 1 calc R U P A 2
C21A C -0.235(6) 0.9467(12) 0.447(4) 0.013(13) Uiso 0.0773(19) 1 d D U P A 2
C20A C -0.075(6) 0.9379(11) 0.421(5) 0.019(16) Uiso 0.0773(19) 1 d D U P A 2
H20A H -0.011499 0.961900 0.400870 0.022 Uiso 0.0773(19) 1 calc R U P A 2
C19A C -0.005(4) 0.8957(10) 0.423(2) 0.009(12) Uiso 0.0773(19) 1 d D U P A 2
C26A C -0.360(7) 0.8350(18) 0.530(4) 0.011(14) Uiso 0.0773(19) 1 d D U P A 2
H26D H -0.340376 0.806098 0.501070 0.017 Uiso 0.0773(19) 1 calc R U P A 2
H26E H -0.482461 0.842542 0.512613 0.017 Uiso 0.0773(19) 1 calc R U P A 2
H26F H -0.326462 0.833899 0.602781 0.017 Uiso 0.0773(19) 1 calc R U P A 2
C25A C -0.305(7) 0.9935(13) 0.438(4) 0.041(17) Uiso 0.0773(19) 1 d D U P A 2
H25D H -0.429456 0.992859 0.435558 0.061 Uiso 0.0773(19) 1 calc R U P A 2
H25E H -0.278775 1.007226 0.376933 0.061 Uiso 0.0773(19) 1 calc R U P A 2
H25F H -0.251253 1.010768 0.496636 0.061 Uiso 0.0773(19) 1 calc R U P A 2
C24A C 0.170(4) 0.8873(15) 0.396(3) 0.014(13) Uiso 0.0773(19) 1 d D U P A 2
H24D H 0.234119 0.866814 0.445251 0.021 Uiso 0.0773(19) 1 calc R U P A 2
H24E H 0.232943 0.915279 0.397673 0.021 Uiso 0.0773(19) 1 calc R U P A 2
H24F H 0.157040 0.874340 0.329180 0.021 Uiso 0.0773(19) 1 calc R U P A 2
P1 P 0.96682(12) 0.61490(3) 0.33013(7) 0.0302(2) Uani 1 1 d . . . . .
F1 F 0.9691(4) 0.63077(12) 0.4416(2) 0.0716(9) Uani 1 1 d . . . . .
F2 F 0.9486(4) 0.56576(10) 0.3664(3) 0.0853(12) Uani 1 1 d . . . . .
F3 F 1.1686(3) 0.61144(12) 0.3539(2) 0.0701(9) Uani 1 1 d . . . . .
F4 F 0.9777(4) 0.66404(9) 0.2929(2) 0.0676(8) Uani 1 1 d . . . . .
F5 F 0.7609(3) 0.61810(10) 0.30600(19) 0.0555(7) Uani 1 1 d . . . . .
F6 F 0.9611(3) 0.59868(11) 0.2179(2) 0.0622(8) Uani 1 1 d . . . . .
P2 P 0.84049(12) 0.72528(3) 0.74415(7) 0.0288(2) Uani 1 1 d . . . . .
F7 F 0.8349(4) 0.71477(10) 0.85836(19) 0.0631(8) Uani 1 1 d . . . . .
F8 F 0.7086(3) 0.68612(9) 0.7114(2) 0.0567(7) Uani 1 1 d . . . . .
F9 F 0.9942(3) 0.69194(11) 0.7472(2) 0.0698(9) Uani 1 1 d . . . . .
F10 F 0.9718(5) 0.76404(11) 0.7785(3) 0.0820(10) Uani 1 1 d . . . . .
F11 F 0.6823(4) 0.75790(10) 0.7404(2) 0.0680(8) Uani 1 1 d . . . . .
F12 F 0.8425(4) 0.73621(11) 0.6298(2) 0.0700(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.836(3) . ?
N1 C1 1.330(4) . ?
N1 C2 1.377(4) . ?
N1 C13 1.469(4) . ?
N2 C1 1.328(4) . ?
N2 C3 1.382(4) . ?
N2 C4 1.454(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.343(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(5) . ?
C4 C9 1.393(5) . ?
C5 C6 1.394(5) . ?
C5 C10 1.504(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(5) . ?
C7 C8 1.378(5) . ?
C7 C11 1.515(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.401(5) . ?
C9 C12 1.510(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 H13C 0.9900 . ?
C13 H13D 0.9900 . ?
C13 C14 1.522(5) . ?
C13 C14A 1.543(19) . ?
Br2 C15 1.836(3) . ?
N3 C14 1.472(5) . ?
N3 C15 1.333(4) . ?
N3 C17 1.377(5) . ?
N4 C15 1.335(4) . ?
N4 C16 1.373(6) . ?
N4 C18 1.457(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C17 1.371(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(5) . ?
C18 C23 1.402(5) . ?
C19 C20 1.398(7) . ?
C19 C24 1.508(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(7) . ?
C21 C22 1.392(6) . ?
C21 C25 1.507(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(5) . ?
C23 C26 1.505(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
Br2A C15A 1.822(17) . ?
N3A C14A 1.47(2) . ?
N3A C15A 1.325(18) . ?
N3A C17A 1.38(2) . ?
N4A C15A 1.316(18) . ?
N4A C16A 1.384(19) . ?
N4A C18A 1.466(17) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C16A H16A 0.9500 . ?
C16A C17A 1.37(2) . ?
C17A H17A 0.9500 . ?
C18A C23A 1.384(18) . ?
C18A C19A 1.393(17) . ?
C23A C22A 1.43(5) . ?
C23A C26A 1.49(5) . ?
C22A H22A 0.9500 . ?
C22A C21A 1.36(4) . ?
C21A C20A 1.392(18) . ?
C21A C25A 1.516(19) . ?
C20A H20A 0.9500 . ?
C20A C19A 1.392(17) . ?
C19A C24A 1.510(17) . ?
C26A H26D 0.9800 . ?
C26A H26E 0.9800 . ?
C26A H26F 0.9800 . ?
C25A H25D 0.9800 . ?
C25A H25E 0.9800 . ?
C25A H25F 0.9800 . ?
C24A H24D 0.9800 . ?
C24A H24E 0.9800 . ?
C24A H24F 0.9800 . ?
P1 F1 1.580(3) . ?
P1 F2 1.579(3) . ?
P1 F3 1.575(3) . ?
P1 F4 1.576(3) . ?
P1 F5 1.607(2) . ?
P1 F6 1.589(3) . ?
P2 F7 1.586(3) . ?
P2 F8 1.590(3) . ?
P2 F9 1.574(3) . ?
P2 F10 1.582(3) . ?
P2 F11 1.587(3) . ?
P2 F12 1.585(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 108.2(3) . . ?
C1 N1 C13 125.7(3) . . ?
C2 N1 C13 125.4(3) . . ?
C1 N2 C3 107.9(3) . . ?
C1 N2 C4 125.4(3) . . ?
C3 N2 C4 126.5(3) . . ?
N1 C1 Br1 125.8(2) . . ?
N2 C1 Br1 125.1(2) . . ?
N2 C1 N1 109.1(3) . . ?
N1 C2 H2 126.4 . . ?
C3 C2 N1 107.2(3) . . ?
C3 C2 H2 126.4 . . ?
N2 C3 H3 126.3 . . ?
C2 C3 N2 107.5(3) . . ?
C2 C3 H3 126.3 . . ?
C5 C4 N2 118.6(3) . . ?
C5 C4 C9 123.6(3) . . ?
C9 C4 N2 117.8(3) . . ?
C4 C5 C6 117.0(3) . . ?
C4 C5 C10 122.4(3) . . ?
C6 C5 C10 120.5(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C11 120.0(3) . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 C11 121.1(3) . . ?
C7 C8 H8 118.9 . . ?
C7 C8 C9 122.2(3) . . ?
C9 C8 H8 118.9 . . ?
C4 C9 C8 116.4(3) . . ?
C4 C9 C12 122.9(3) . . ?
C8 C9 C12 120.7(3) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
N1 C13 H13C 109.5 . . ?
N1 C13 H13D 109.5 . . ?
N1 C13 C14 112.1(3) . . ?
N1 C13 C14A 111(2) . . ?
H13A C13 H13B 107.9 . . ?
H13C C13 H13D 108.1 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C14A C13 H13C 109.5 . . ?
C14A C13 H13D 109.5 . . ?
C15 N3 C14 125.1(3) . . ?
C15 N3 C17 108.6(3) . . ?
C17 N3 C14 126.2(3) . . ?
C15 N4 C16 108.3(3) . . ?
C15 N4 C18 129.1(3) . . ?
C16 N4 C18 122.2(3) . . ?
C13 C14 H14A 110.2 . . ?
C13 C14 H14B 110.2 . . ?
N3 C14 C13 107.6(3) . . ?
N3 C14 H14A 110.2 . . ?
N3 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
N3 C15 Br2 126.2(3) . . ?
N3 C15 N4 109.1(3) . . ?
N4 C15 Br2 124.5(3) . . ?
N4 C16 H16 126.3 . . ?
C17 C16 N4 107.4(4) . . ?
C17 C16 H16 126.3 . . ?
N3 C17 H17 126.7 . . ?
C16 C17 N3 106.6(4) . . ?
C16 C17 H17 126.7 . . ?
C19 C18 N4 120.8(3) . . ?
C19 C18 C23 123.6(4) . . ?
C23 C18 N4 115.6(3) . . ?
C18 C19 C20 116.5(4) . . ?
C18 C19 C24 122.7(5) . . ?
C20 C19 C24 120.8(4) . . ?
C19 C20 H20 118.7 . . ?
C21 C20 C19 122.6(4) . . ?
C21 C20 H20 118.7 . . ?
C20 C21 C22 118.6(4) . . ?
C20 C21 C25 121.1(4) . . ?
C22 C21 C25 120.3(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.3(4) . . ?
C23 C22 H22 119.3 . . ?
C18 C23 C26 122.5(4) . . ?
C22 C23 C18 117.5(4) . . ?
C22 C23 C26 120.0(4) . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C15A N3A C14A 129(3) . . ?
C15A N3A C17A 106.3(18) . . ?
C17A N3A C14A 125(3) . . ?
C15A N4A C16A 104.8(17) . . ?
C15A N4A C18A 135.3(16) . . ?
C16A N4A C18A 119.9(16) . . ?
C13 C14A H14C 107.0 . . ?
C13 C14A H14D 107.0 . . ?
N3A C14A C13 121.4(19) . . ?
N3A C14A H14C 107.0 . . ?
N3A C14A H14D 107.0 . . ?
H14C C14A H14D 106.7 . . ?
N3A C15A Br2A 124.8(18) . . ?
N4A C15A Br2A 121.6(17) . . ?
N4A C15A N3A 113.6(17) . . ?
N4A C16A H16A 125.5 . . ?
C17A C16A N4A 109.0(19) . . ?
C17A C16A H16A 125.5 . . ?
N3A C17A H17A 126.8 . . ?
C16A C17A N3A 106.3(19) . . ?
C16A C17A H17A 126.8 . . ?
C23A C18A N4A 114.2(19) . . ?
C23A C18A C19A 123(2) . . ?
C19A C18A N4A 122.3(16) . . ?
C18A C23A C22A 118(3) . . ?
C18A C23A C26A 126(3) . . ?
C22A C23A C26A 117(3) . . ?
C23A C22A H22A 119.8 . . ?
C21A C22A C23A 120(3) . . ?
C21A C22A H22A 119.8 . . ?
C22A C21A C20A 119(2) . . ?
C22A C21A C25A 121(3) . . ?
C20A C21A C25A 120(3) . . ?
C21A C20A H20A 118.4 . . ?
C21A C20A C19A 123(2) . . ?
C19A C20A H20A 118.4 . . ?
C18A C19A C24A 122(2) . . ?
C20A C19A C18A 116(2) . . ?
C20A C19A C24A 122(2) . . ?
C23A C26A H26D 109.5 . . ?
C23A C26A H26E 109.5 . . ?
C23A C26A H26F 109.5 . . ?
H26D C26A H26E 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?
C21A C25A H25D 109.5 . . ?
C21A C25A H25E 109.5 . . ?
C21A C25A H25F 109.5 . . ?
H25D C25A H25E 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?
C19A C24A H24D 109.5 . . ?
C19A C24A H24E 109.5 . . ?
C19A C24A H24F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
F1 P1 F5 91.20(17) . . ?
F1 P1 F6 179.01(18) . . ?
F2 P1 F1 88.6(2) . . ?
F2 P1 F5 88.65(17) . . ?
F2 P1 F6 91.0(2) . . ?
F3 P1 F1 88.84(18) . . ?
F3 P1 F2 90.99(18) . . ?
F3 P1 F4 91.10(18) . . ?
F3 P1 F5 179.64(18) . . ?
F3 P1 F6 92.08(17) . . ?
F4 P1 F1 91.50(18) . . ?
F4 P1 F2 177.90(18) . . ?
F4 P1 F5 89.26(16) . . ?
F4 P1 F6 88.85(18) . . ?
F6 P1 F5 87.87(15) . . ?
F7 P2 F8 89.78(17) . . ?
F7 P2 F11 90.12(17) . . ?
F9 P2 F7 89.82(18) . . ?
F9 P2 F8 89.80(16) . . ?
F9 P2 F10 90.2(2) . . ?
F9 P2 F11 178.58(19) . . ?
F9 P2 F12 91.25(18) . . ?
F10 P2 F7 89.34(18) . . ?
F10 P2 F8 179.12(19) . . ?
F10 P2 F11 91.3(2) . . ?
F10 P2 F12 90.93(19) . . ?
F11 P2 F8 88.78(17) . . ?
F12 P2 F7 178.90(19) . . ?
F12 P2 F8 89.95(17) . . ?
F12 P2 F11 88.81(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 0.2(4) . . . . ?
N1 C13 C14 N3 177.6(3) . . . . ?
N1 C13 C14A N3A -139(4) . . . . ?
N2 C4 C5 C6 -175.1(3) . . . . ?
N2 C4 C5 C10 6.5(5) . . . . ?
N2 C4 C9 C8 177.3(3) . . . . ?
N2 C4 C9 C12 -2.5(5) . . . . ?
C1 N1 C2 C3 -0.1(4) . . . . ?
C1 N1 C13 C14 -79.3(5) . . . . ?
C1 N1 C13 C14A -61(2) . . . . ?
C1 N2 C3 C2 -0.3(4) . . . . ?
C1 N2 C4 C5 76.4(4) . . . . ?
C1 N2 C4 C9 -102.3(4) . . . . ?
C2 N1 C1 Br1 178.8(3) . . . . ?
C2 N1 C1 N2 -0.1(4) . . . . ?
C2 N1 C13 C14 111.7(4) . . . . ?
C2 N1 C13 C14A 130(2) . . . . ?
C3 N2 C1 Br1 -178.7(3) . . . . ?
C3 N2 C1 N1 0.2(4) . . . . ?
C3 N2 C4 C5 -109.5(4) . . . . ?
C3 N2 C4 C9 71.8(4) . . . . ?
C4 N2 C1 Br1 -3.7(5) . . . . ?
C4 N2 C1 N1 175.3(3) . . . . ?
C4 N2 C3 C2 -175.2(3) . . . . ?
C4 C5 C6 C7 -2.4(5) . . . . ?
C5 C4 C9 C8 -1.3(5) . . . . ?
C5 C4 C9 C12 178.9(3) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C5 C6 C7 C11 178.1(3) . . . . ?
C6 C7 C8 C9 3.0(5) . . . . ?
C7 C8 C9 C4 -2.1(5) . . . . ?
C7 C8 C9 C12 177.7(3) . . . . ?
C9 C4 C5 C6 3.5(5) . . . . ?
C9 C4 C5 C10 -174.9(3) . . . . ?
C10 C5 C6 C7 176.0(3) . . . . ?
C11 C7 C8 C9 -175.7(3) . . . . ?
C13 N1 C1 Br1 8.3(5) . . . . ?
C13 N1 C1 N2 -170.7(3) . . . . ?
C13 N1 C2 C3 170.5(3) . . . . ?
N4 C16 C17 N3 0.8(5) . . . . ?
N4 C18 C19 C20 177.4(5) . . . . ?
N4 C18 C19 C24 -0.5(7) . . . . ?
N4 C18 C23 C22 -176.4(5) . . . . ?
N4 C18 C23 C26 4.3(6) . . . . ?
C14 N3 C15 Br2 5.3(5) . . . . ?
C14 N3 C15 N4 -179.7(3) . . . . ?
C14 N3 C17 C16 179.6(4) . . . . ?
C15 N3 C14 C13 145.4(4) . . . . ?
C15 N3 C17 C16 -1.2(5) . . . . ?
C15 N4 C16 C17 -0.2(5) . . . . ?
C15 N4 C18 C19 78.6(5) . . . . ?
C15 N4 C18 C23 -104.5(4) . . . . ?
C16 N4 C15 Br2 174.6(3) . . . . ?
C16 N4 C15 N3 -0.5(4) . . . . ?
C16 N4 C18 C19 -109.3(5) . . . . ?
C16 N4 C18 C23 67.6(5) . . . . ?
C17 N3 C14 C13 -35.5(6) . . . . ?
C17 N3 C15 Br2 -173.9(3) . . . . ?
C17 N3 C15 N4 1.0(4) . . . . ?
C18 N4 C15 Br2 -12.5(5) . . . . ?
C18 N4 C15 N3 172.4(3) . . . . ?
C18 N4 C16 C17 -173.7(3) . . . . ?
C18 C19 C20 C21 -2.7(9) . . . . ?
C19 C18 C23 C22 0.4(7) . . . . ?
C19 C18 C23 C26 -178.9(5) . . . . ?
C19 C20 C21 C22 3.4(9) . . . . ?
C19 C20 C21 C25 -175.5(6) . . . . ?
C20 C21 C22 C23 -2.1(9) . . . . ?
C21 C22 C23 C18 0.3(8) . . . . ?
C21 C22 C23 C26 179.6(5) . . . . ?
C23 C18 C19 C20 0.7(8) . . . . ?
C23 C18 C19 C24 -177.2(5) . . . . ?
C24 C19 C20 C21 175.3(6) . . . . ?
C25 C21 C22 C23 176.8(6) . . . . ?
N4A C16A C17A N3A -0.6(18) . . . . ?
N4A C18A C23A C22A -179(4) . . . . ?
N4A C18A C23A C26A 3(5) . . . . ?
N4A C18A C19A C20A 180(3) . . . . ?
N4A C18A C19A C24A -4(2) . . . . ?
C14A N3A C15A Br2A -1(2) . . . . ?
C14A N3A C15A N4A 179.8(11) . . . . ?
C14A N3A C17A C16A -179.5(13) . . . . ?
C15A N3A C14A C13 -75(4) . . . . ?
C15A N3A C17A C16A 0.5(17) . . . . ?
C15A N4A C16A C17A 0.5(17) . . . . ?
C15A N4A C18A C23A -103(3) . . . . ?
C15A N4A C18A C19A 75.6(19) . . . . ?
C16A N4A C15A Br2A -179.9(12) . . . . ?
C16A N4A C15A N3A -0.2(16) . . . . ?
C16A N4A C18A C23A 77(3) . . . . ?
C16A N4A C18A C19A -103.7(15) . . . . ?
C17A N3A C14A C13 105(4) . . . . ?
C17A N3A C15A Br2A 179.5(13) . . . . ?
C17A N3A C15A N4A -0.1(17) . . . . ?
C18A N4A C15A Br2A 1(2) . . . . ?
C18A N4A C15A N3A -179.5(11) . . . . ?
C18A N4A C16A C17A 180.0(13) . . . . ?
C18A C23A C22A C21A 1(7) . . . . ?
C23A C18A C19A C20A -1(4) . . . . ?
C23A C18A C19A C24A 175(3) . . . . ?
C23A C22A C21A C20A -4(8) . . . . ?
C23A C22A C21A C25A 178(5) . . . . ?
C22A C21A C20A C19A 5(8) . . . . ?
C21A C20A C19A C18A -2(6) . . . . ?
C21A C20A C19A C24A -179(4) . . . . ?
C19A C18A C23A C22A 2(6) . . . . ?
C19A C18A C23A C26A -176(3) . . . . ?
C26A C23A C22A C21A 179(5) . . . . ?
C25A C21A C20A C19A -178(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'



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

data_Compound2BrPF6
_database_code_depnum_ccdc_archive 'CCDC 2212883'
loop_
_audit_author_name
_audit_author_address
'Nathan L. Kilah'
;University of Tasmania
Australia
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT434_Compound2BrPF6      
;
PROBLEM: Short Inter HL..HL Contact Br1      ..Br3      .       3.08 Ang.
RESPONSE: Halogen bond.
;
_vrf_PLAT434_Compound2BrPF6_2    
;
PROBLEM: Short Inter HL..HL Contact Br2      ..Br3      .       3.17 Ang.
RESPONSE: Halogen bond.
;
_vrf_PLAT042_Compound2BrPF6      
;
PROBLEM: Calc. and Reported MoietyFormula Strings  Differ     Please Check
RESPONSE: Reported Moiety Formula more accurately represents the observed structure.
;

_vrf_PLAT094_Compound2BrPF6      
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.59 Report
RESPONSE: A relatively large Q-peak remains (1.8).
;
_vrf_PLAT220_Compound2BrPF6      
;
PROBLEM: NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.5 Ratio
RESPONSE: The mesityl groups of the main reside had high thermal parameters Attempts were made to model the mesityl ring over two different positions of unequal occupancy, but this was unsuccessful and did not give a stable refinement.
;
_vrf_PLAT250_Compound2BrPF6      
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.5 Note
RESPONSE: The mesityl groups of the main reside had high thermal parameters Attempts were made to model the mesityl ring over two different positions of unequal occupancy, but this was unsuccessful and did not give a stable refinement.
;
_vrf_PLAT341_Compound2BrPF6      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00985 Ang.
RESPONSE: Data were relatively weak. The crystals were large, but diffracted poorly.
;
# Added during the CSD deposition process: Friday 14 October 2022 03:02 AM
# end Validation Reply Form

_audit_creation_date             2020-05-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H28 Br2 N4, Br, 2(F3 P0.5)'
_chemical_formula_sum            'C25 H28 Br3 F6 N4 P'
_chemical_formula_weight         769.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   16.5294(8)
_cell_length_b                   12.7951(7)
_cell_length_c                   16.2419(8)
_cell_angle_alpha                90
_cell_angle_beta                 117.328(3)
_cell_angle_gamma                90
_cell_volume                     3051.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9758
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      66.46
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   0.589
_shelx_estimated_absorpt_T_min   0.384
_exptl_absorpt_coefficient_mu    5.928
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1237 before and 0.0847 after correction.
The Ratio of minimum to maximum transmission is 0.6849.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1181
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            50630
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.752
_diffrn_reflns_theta_max         66.752
_diffrn_reflns_theta_min         3.009
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  
'Bruker multilayer X-ray optics (Goebel mirror)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4004
_reflns_number_total             5403
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0  (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'enCIFer (Allen, 1997)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.792
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0219P)²+13.6720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1242
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F4(0.5) F6(0.5) F8(0.5) F5(0.5) F9(0.5) F7(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C19(H19), C15(H15), C21(H21), C16(H16), C2(H2), C8(H8), C6(H6)
3.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C12(H12A,H12B,
 H12C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.73725(4) 0.64901(5) 0.41843(4) 0.03630(17) Uani 1 1 d . . . . .
Br2 Br 0.97967(4) 0.35211(5) 0.62314(4) 0.03800(18) Uani 1 1 d . . . . .
Br3 Br 0.80493(4) 0.63733(5) 0.27110(4) 0.03756(18) Uani 1 1 d . . . . .
P1 P 1.000000 0.73740(17) 0.750000 0.0412(5) Uani 1 2 d S T P . .
P2 P 0.500000 0.2910(3) 0.250000 0.0540(7) Uani 1 2 d S T P . .
F3 F 0.9080(3) 0.7373(3) 0.6545(3) 0.0626(11) Uani 1 1 d . . . . .
F1 F 0.9584(3) 0.8260(3) 0.7880(3) 0.0620(11) Uani 1 1 d . . . . .
F2 F 0.9596(3) 0.6487(3) 0.7890(3) 0.0644(11) Uani 1 1 d . . . . .
N2 N 0.7544(3) 0.5907(4) 0.5931(3) 0.0308(10) Uani 1 1 d . . . . .
N4 N 0.7988(3) 0.4214(4) 0.5674(3) 0.0289(10) Uani 1 1 d . . . . .
N3 N 0.8035(3) 0.2601(4) 0.5285(3) 0.0303(10) Uani 1 1 d . . . . .
N1 N 0.6431(3) 0.6990(4) 0.5241(3) 0.0316(10) Uani 1 1 d . . . . .
C1 C 0.7093(3) 0.6473(4) 0.5160(4) 0.0292(12) Uani 1 1 d . . . . .
C20 C 0.8871(4) -0.0280(4) 0.4707(4) 0.0346(13) Uani 1 1 d . . . . .
C4 C 0.5738(4) 0.7644(4) 0.4539(4) 0.0325(13) Uani 1 1 d . . . . .
C22 C 0.8329(4) 0.1481(5) 0.4249(4) 0.0339(12) Uani 1 1 d . . . . .
C17 C 0.8351(4) 0.1614(4) 0.5111(4) 0.0307(12) Uani 1 1 d . . . . .
C3 C 0.6467(4) 0.6732(5) 0.6095(4) 0.0341(13) Uani 1 1 d . . . . .
H3 H 0.606962 0.698295 0.632604 0.041 Uiso 1 1 calc R U . . .
C19 C 0.8899(4) -0.0115(4) 0.5567(4) 0.0367(14) Uani 1 1 d . . . . .
H19 H 0.909443 -0.066500 0.600838 0.044 Uiso 1 1 calc R U . . .
C13 C 0.8317(4) 0.5237(4) 0.6127(4) 0.0333(13) Uani 1 1 d . . . . .
H13A H 0.867780 0.514051 0.680523 0.040 Uiso 1 1 calc R U . . .
H13B H 0.871381 0.556376 0.589267 0.040 Uiso 1 1 calc R U . . .
C14 C 0.8537(4) 0.3441(4) 0.5699(4) 0.0305(12) Uani 1 1 d . . . . .
C18 C 0.8643(4) 0.0852(5) 0.5797(4) 0.0334(13) Uani 1 1 d . . . . .
C15 C 0.7102(4) 0.3851(5) 0.5236(5) 0.0415(15) Uani 1 1 d . . . . .
H15 H 0.657098 0.423327 0.513173 0.050 Uiso 1 1 calc R U . . .
C21 C 0.8602(4) 0.0513(5) 0.4082(4) 0.0370(14) Uani 1 1 d . . . . .
H21 H 0.860090 0.040007 0.350348 0.044 Uiso 1 1 calc R U . . .
C16 C 0.7133(4) 0.2858(5) 0.4985(4) 0.0369(14) Uani 1 1 d . . . . .
H16 H 0.662440 0.241294 0.465866 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7156(4) 0.6074(5) 0.6524(4) 0.0387(14) Uani 1 1 d . . . . .
H2 H 0.734807 0.577471 0.712013 0.046 Uiso 1 1 calc R U . . .
C9 C 0.4955(4) 0.7162(5) 0.3883(5) 0.0415(14) Uani 1 1 d . . . . .
C25 C 0.8039(5) 0.2351(6) 0.3540(5) 0.0497(17) Uani 1 1 d . . . . .
H25A H 0.740949 0.255255 0.336915 0.075 Uiso 1 1 calc R U . . .
H25B H 0.807881 0.210886 0.298726 0.075 Uiso 1 1 calc R U . . .
H25C H 0.843981 0.295573 0.380340 0.075 Uiso 1 1 calc R U . . .
C23 C 0.8655(5) 0.1016(5) 0.6713(4) 0.0440(15) Uani 1 1 d . . . . .
H23A H 0.905583 0.160483 0.703341 0.066 Uiso 1 1 calc R U . . .
H23B H 0.888144 0.038278 0.709038 0.066 Uiso 1 1 calc R U . . .
H23C H 0.803707 0.116722 0.661746 0.066 Uiso 1 1 calc R U . . .
C5 C 0.5860(5) 0.8709(5) 0.4578(6) 0.0543(18) Uani 1 1 d . . . . .
C7 C 0.4364(5) 0.8868(6) 0.3237(5) 0.0517(18) Uani 1 1 d . . . . .
C24 C 0.9142(5) -0.1332(5) 0.4489(5) 0.0487(17) Uani 1 1 d . . . . .
H24A H 0.940397 -0.176167 0.505070 0.073 Uiso 1 1 calc R U . . .
H24B H 0.959405 -0.123416 0.426281 0.073 Uiso 1 1 calc R U . . .
H24C H 0.860348 -0.168151 0.401108 0.073 Uiso 1 1 calc R U . . .
C8 C 0.4282(4) 0.7801(6) 0.3250(5) 0.0503(17) Uani 1 1 d . . . . .
H8 H 0.373577 0.748692 0.280175 0.060 Uiso 1 1 calc R U . . .
C6 C 0.5158(5) 0.9306(6) 0.3911(6) 0.067(2) Uani 1 1 d . . . . .
H6 H 0.522764 1.004316 0.392047 0.080 Uiso 1 1 calc R U . . .
C12 C 0.4843(6) 0.5998(6) 0.3847(7) 0.075(3) Uani 1 1 d . . . . .
H12A H 0.524539 0.568036 0.362372 0.112 Uiso 1 1 calc R U . . .
H12B H 0.420902 0.581839 0.342419 0.112 Uiso 1 1 calc R U . . .
H12C H 0.500003 0.573311 0.446820 0.112 Uiso 1 1 calc R U . . .
C11 C 0.3611(6) 0.9530(7) 0.2531(7) 0.082(3) Uani 1 1 d . . . . .
H11A H 0.365977 0.953824 0.195220 0.123 Uiso 1 1 calc R U . . .
H11B H 0.366315 1.024471 0.276686 0.123 Uiso 1 1 calc R U . . .
H11C H 0.302001 0.923711 0.241487 0.123 Uiso 1 1 calc R U . . .
C10 C 0.6713(6) 0.9212(7) 0.5320(8) 0.103(4) Uani 1 1 d . . . . .
H10A H 0.682914 0.894200 0.592965 0.155 Uiso 1 1 calc R U . . .
H10B H 0.662955 0.997105 0.530622 0.155 Uiso 1 1 calc R U . . .
H10C H 0.723157 0.904788 0.520580 0.155 Uiso 1 1 calc R U . . .
F4 F 0.5846(10) 0.3574(14) 0.2626(10) 0.075(4) Uani 0.5 1 d . . P . .
F6 F 0.5223(5) 0.3324(8) 0.3551(5) 0.050(2) Uani 0.5 1 d . . P . .
F8 F 0.4247(7) 0.2191(10) 0.2505(9) 0.081(4) Uani 0.5 1 d . . P . .
F5 F 0.5745(7) 0.1976(9) 0.3034(8) 0.080(3) Uani 0.5 1 d . . P . .
F9 F 0.4886(6) 0.2438(12) 0.1586(6) 0.082(4) Uani 0.5 1 d . . P . .
F7 F 0.4337(11) 0.3838(15) 0.2089(11) 0.098(5) Uani 0.5 1 d . . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.842(6) . ?
Br2 C14 1.855(5) . ?
P1 F3 1.597(4) 2_756 ?
P1 F3 1.597(4) . ?
P1 F1 1.590(4) . ?
P1 F1 1.590(4) 2_756 ?
P1 F2 1.589(4) . ?
P1 F2 1.589(4) 2_756 ?
P2 F4 1.567(14) . ?
P2 F4 1.567(14) 2_655 ?
P2 F6 1.659(8) 2_655 ?
P2 F6 1.659(8) . ?
P2 F8 1.552(10) . ?
P2 F8 1.552(10) 2_655 ?
P2 F5 1.649(11) . ?
P2 F5 1.649(11) 2_655 ?
P2 F9 1.531(8) 2_655 ?
P2 F9 1.531(8) . ?
P2 F7 1.544(17) 2_655 ?
P2 F7 1.544(17) . ?
N2 C1 1.339(7) . ?
N2 C13 1.448(7) . ?
N2 C2 1.397(7) . ?
N4 C13 1.478(7) . ?
N4 C14 1.329(7) . ?
N4 C15 1.382(7) . ?
N3 C17 1.443(7) . ?
N3 C14 1.336(7) . ?
N3 C16 1.379(7) . ?
N1 C1 1.337(7) . ?
N1 C4 1.453(7) . ?
N1 C3 1.400(7) . ?
C20 C19 1.392(8) . ?
C20 C21 1.358(9) . ?
C20 C24 1.511(8) . ?
C4 C9 1.388(8) . ?
C4 C5 1.374(9) . ?
C22 C17 1.393(8) . ?
C22 C21 1.387(8) . ?
C22 C25 1.513(8) . ?
C17 C18 1.391(8) . ?
C3 H3 0.9500 . ?
C3 C2 1.327(8) . ?
C19 H19 0.9500 . ?
C19 C18 1.412(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C18 C23 1.494(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.343(9) . ?
C21 H21 0.9500 . ?
C16 H16 0.9500 . ?
C2 H2 0.9500 . ?
C9 C8 1.384(9) . ?
C9 C12 1.499(9) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C5 C6 1.397(10) . ?
C5 C10 1.514(10) . ?
C7 C8 1.372(10) . ?
C7 C6 1.384(11) . ?
C7 C11 1.508(10) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F3 P1 F3 179.9(3) . 2_756 ?
F1 P1 F3 89.4(2) 2_756 2_756 ?
F1 P1 F3 90.7(2) . 2_756 ?
F1 P1 F3 89.4(2) . . ?
F1 P1 F3 90.7(2) 2_756 . ?
F1 P1 F1 89.1(3) . 2_756 ?
F2 P1 F3 90.0(2) 2_756 . ?
F2 P1 F3 90.0(2) 2_756 2_756 ?
F2 P1 F3 90.0(2) . 2_756 ?
F2 P1 F3 90.0(2) . . ?
F2 P1 F1 179.3(3) 2_756 . ?
F2 P1 F1 91.1(2) 2_756 2_756 ?
F2 P1 F1 179.3(3) . 2_756 ?
F2 P1 F1 91.0(2) . . ?
F2 P1 F2 88.8(3) 2_756 . ?
F4 P2 F4 114.4(13) 2_655 . ?
F4 P2 F6 74.1(6) 2_655 . ?
F4 P2 F6 74.1(6) . 2_655 ?
F4 P2 F6 86.0(5) 2_655 2_655 ?
F4 P2 F6 86.0(5) . . ?
F4 P2 F5 85.3(8) . . ?
F4 P2 F5 150.2(7) . 2_655 ?
F4 P2 F5 85.3(8) 2_655 2_655 ?
F4 P2 F5 150.2(7) 2_655 . ?
F6 P2 F6 142.8(7) . 2_655 ?
F8 P2 F4 69.6(7) . 2_655 ?
F8 P2 F4 69.6(7) 2_655 . ?
F8 P2 F4 172.3(8) . . ?
F8 P2 F4 172.3(8) 2_655 2_655 ?
F8 P2 F6 89.0(5) 2_655 2_655 ?
F8 P2 F6 113.3(6) 2_655 . ?
F8 P2 F6 89.0(5) . . ?
F8 P2 F6 113.3(6) . 2_655 ?
F8 P2 F8 107.3(9) 2_655 . ?
F8 P2 F5 88.6(6) . . ?
F8 P2 F5 88.6(6) 2_655 2_655 ?
F5 P2 F6 122.1(5) . 2_655 ?
F5 P2 F6 122.1(5) 2_655 . ?
F5 P2 F6 86.0(5) 2_655 2_655 ?
F5 P2 F6 86.0(5) . . ?
F5 P2 F5 87.0(8) . 2_655 ?
F9 P2 F4 92.6(6) . . ?
F9 P2 F4 112.4(7) 2_655 . ?
F9 P2 F4 112.4(7) . 2_655 ?
F9 P2 F4 92.6(6) 2_655 2_655 ?
F9 P2 F6 173.3(7) . . ?
F9 P2 F6 173.3(7) 2_655 2_655 ?
F9 P2 F8 91.7(6) 2_655 2_655 ?
F9 P2 F8 91.7(6) . . ?
F9 P2 F5 87.4(7) . . ?
F9 P2 F5 87.4(7) 2_655 2_655 ?
F9 P2 F9 133.6(12) 2_655 . ?
F9 P2 F7 97.9(9) . . ?
F9 P2 F7 97.9(9) 2_655 2_655 ?
F9 P2 F7 118.0(8) . 2_655 ?
F9 P2 F7 118.0(8) 2_655 . ?
F7 P2 F4 93.1(8) . . ?
F7 P2 F4 93.1(8) 2_655 2_655 ?
F7 P2 F6 88.7(8) . . ?
F7 P2 F6 88.7(8) 2_655 2_655 ?
F7 P2 F8 92.6(8) . . ?
F7 P2 F8 92.6(8) 2_655 2_655 ?
F7 P2 F5 96.9(8) . 2_655 ?
F7 P2 F5 96.9(8) 2_655 . ?
F7 P2 F5 174.6(8) 2_655 2_655 ?
F7 P2 F5 174.6(8) . . ?
C1 N2 C13 125.6(5) . . ?
C1 N2 C2 109.2(5) . . ?
C2 N2 C13 125.2(5) . . ?
C14 N4 C13 123.6(4) . . ?
C14 N4 C15 108.2(5) . . ?
C15 N4 C13 127.9(5) . . ?
C14 N3 C17 127.3(4) . . ?
C14 N3 C16 107.8(5) . . ?
C16 N3 C17 124.7(5) . . ?
C1 N1 C4 126.4(5) . . ?
C1 N1 C3 108.5(5) . . ?
C3 N1 C4 124.9(4) . . ?
N2 C1 Br1 124.1(4) . . ?
N1 C1 Br1 128.2(4) . . ?
N1 C1 N2 107.7(5) . . ?
C19 C20 C24 119.6(6) . . ?
C21 C20 C19 119.0(5) . . ?
C21 C20 C24 121.4(6) . . ?
C9 C4 N1 117.9(5) . . ?
C5 C4 N1 119.2(5) . . ?
C5 C4 C9 122.8(6) . . ?
C17 C22 C25 121.8(5) . . ?
C21 C22 C17 116.4(5) . . ?
C21 C22 C25 121.7(5) . . ?
C22 C17 N3 117.3(5) . . ?
C18 C17 N3 118.7(5) . . ?
C18 C17 C22 124.0(5) . . ?
N1 C3 H3 126.1 . . ?
C2 C3 N1 107.8(5) . . ?
C2 C3 H3 126.1 . . ?
C20 C19 H19 119.2 . . ?
C20 C19 C18 121.6(6) . . ?
C18 C19 H19 119.2 . . ?
N2 C13 N4 109.2(4) . . ?
N2 C13 H13A 109.8 . . ?
N2 C13 H13B 109.8 . . ?
N4 C13 H13A 109.8 . . ?
N4 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
N4 C14 Br2 125.3(4) . . ?
N4 C14 N3 109.0(5) . . ?
N3 C14 Br2 125.7(4) . . ?
C17 C18 C19 115.9(5) . . ?
C17 C18 C23 122.8(5) . . ?
C19 C18 C23 121.2(5) . . ?
N4 C15 H15 126.4 . . ?
C16 C15 N4 107.2(5) . . ?
C16 C15 H15 126.4 . . ?
C20 C21 C22 123.1(6) . . ?
C20 C21 H21 118.5 . . ?
C22 C21 H21 118.5 . . ?
N3 C16 H16 126.2 . . ?
C15 C16 N3 107.7(5) . . ?
C15 C16 H16 126.2 . . ?
N2 C2 H2 126.6 . . ?
C3 C2 N2 106.8(5) . . ?
C3 C2 H2 126.6 . . ?
C4 C9 C12 121.8(6) . . ?
C8 C9 C4 117.1(6) . . ?
C8 C9 C12 121.0(6) . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C5 C6 117.0(6) . . ?
C4 C5 C10 121.4(7) . . ?
C6 C5 C10 121.6(7) . . ?
C8 C7 C6 117.1(6) . . ?
C8 C7 C11 121.1(7) . . ?
C6 C7 C11 121.7(7) . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 C8 H8 118.4 . . ?
C7 C8 C9 123.2(6) . . ?
C7 C8 H8 118.4 . . ?
C5 C6 H6 118.6 . . ?
C7 C6 C5 122.7(7) . . ?
C7 C6 H6 118.6 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C15 C16 N3 1.3(7) . . . . ?
N3 C17 C18 C19 176.8(5) . . . . ?
N3 C17 C18 C23 -0.8(8) . . . . ?
N1 C4 C9 C8 176.7(5) . . . . ?
N1 C4 C9 C12 -4.2(10) . . . . ?
N1 C4 C5 C6 -177.4(6) . . . . ?
N1 C4 C5 C10 1.7(11) . . . . ?
N1 C3 C2 N2 -0.9(7) . . . . ?
C1 N2 C13 N4 -82.7(6) . . . . ?
C1 N2 C2 C3 0.7(7) . . . . ?
C1 N1 C4 C9 85.5(7) . . . . ?
C1 N1 C4 C5 -97.8(7) . . . . ?
C1 N1 C3 C2 0.8(6) . . . . ?
C20 C19 C18 C17 1.0(8) . . . . ?
C20 C19 C18 C23 178.6(5) . . . . ?
C4 N1 C1 Br1 4.0(8) . . . . ?
C4 N1 C1 N2 -175.7(5) . . . . ?
C4 N1 C3 C2 176.2(5) . . . . ?
C4 C9 C8 C7 1.1(10) . . . . ?
C4 C5 C6 C7 0.5(12) . . . . ?
C22 C17 C18 C19 -2.2(8) . . . . ?
C22 C17 C18 C23 -179.8(6) . . . . ?
C17 N3 C14 Br2 -4.3(8) . . . . ?
C17 N3 C14 N4 176.0(5) . . . . ?
C17 N3 C16 C15 -176.9(5) . . . . ?
C17 C22 C21 C20 0.6(8) . . . . ?
C3 N1 C1 Br1 179.4(4) . . . . ?
C3 N1 C1 N2 -0.3(6) . . . . ?
C3 N1 C4 C9 -89.2(7) . . . . ?
C3 N1 C4 C5 87.6(7) . . . . ?
C19 C20 C21 C22 -1.7(9) . . . . ?
C13 N2 C1 Br1 0.7(8) . . . . ?
C13 N2 C1 N1 -179.6(5) . . . . ?
C13 N2 C2 C3 -179.9(5) . . . . ?
C13 N4 C14 Br2 -4.2(8) . . . . ?
C13 N4 C14 N3 175.5(5) . . . . ?
C13 N4 C15 C16 -175.8(5) . . . . ?
C14 N4 C13 N2 177.6(5) . . . . ?
C14 N4 C15 C16 -1.2(7) . . . . ?
C14 N3 C17 C22 -94.0(7) . . . . ?
C14 N3 C17 C18 86.9(7) . . . . ?
C14 N3 C16 C15 -1.0(7) . . . . ?
C15 N4 C13 N2 -8.6(8) . . . . ?
C15 N4 C14 Br2 -179.1(4) . . . . ?
C15 N4 C14 N3 0.7(6) . . . . ?
C21 C20 C19 C18 0.8(8) . . . . ?
C21 C22 C17 N3 -177.6(5) . . . . ?
C21 C22 C17 C18 1.5(8) . . . . ?
C16 N3 C17 C22 81.2(7) . . . . ?
C16 N3 C17 C18 -97.9(7) . . . . ?
C16 N3 C14 Br2 179.9(4) . . . . ?
C16 N3 C14 N4 0.2(6) . . . . ?
C2 N2 C1 Br1 -179.9(4) . . . . ?
C2 N2 C1 N1 -0.2(6) . . . . ?
C2 N2 C13 N4 98.1(6) . . . . ?
C9 C4 C5 C6 -0.8(11) . . . . ?
C9 C4 C5 C10 178.3(8) . . . . ?
C25 C22 C17 N3 3.4(8) . . . . ?
C25 C22 C17 C18 -177.6(6) . . . . ?
C25 C22 C21 C20 179.6(6) . . . . ?
C5 C4 C9 C8 0.1(10) . . . . ?
C5 C4 C9 C12 179.2(7) . . . . ?
C24 C20 C19 C18 -179.3(5) . . . . ?
C24 C20 C21 C22 178.5(5) . . . . ?
C8 C7 C6 C5 0.6(12) . . . . ?
C6 C7 C8 C9 -1.4(11) . . . . ?
C12 C9 C8 C7 -178.0(7) . . . . ?
C11 C7 C8 C9 179.8(7) . . . . ?
C11 C7 C6 C5 179.3(8) . . . . ?
C10 C5 C6 C7 -178.6(9) . . . . ?
F4 P2 F4 F7 42(2) 2_655 . . 2_655 ?
F4 P2 F6 F9 112.8(9) 2_655 . . 2_655 ?
F4 P2 F6 F9 -130.4(9) . . . 2_655 ?
F4 P2 F6 F7 14.4(12) . . . 2_655 ?
F4 P2 F6 F7 -102.4(9) 2_655 . . 2_655 ?
F4 P2 F8 F5 113.9(14) 2_655 . . 2_655 ?
F4 P2 F8 F9 -105.6(9) 2_655 . . 2_655 ?
F4 P2 F5 F8 167.0(17) 2_655 . . 2_655 ?
F4 P2 F5 F8 -59.3(13) . . . 2_655 ?
F4 P2 F5 F9 -13.6(17) 2_655 . . 2_655 ?
F4 P2 F5 F9 120.1(8) . . . 2_655 ?
F4 P2 F9 F6 55.2(9) 2_655 . . 2_655 ?
F4 P2 F9 F6 -62.5(9) . . . 2_655 ?
F4 P2 F9 F8 64.6(9) . . . 2_655 ?
F4 P2 F9 F8 -177.6(9) 2_655 . . 2_655 ?
F4 P2 F9 F5 173.3(9) . . . 2_655 ?
F4 P2 F9 F5 -68.9(9) 2_655 . . 2_655 ?
F4 P2 F7 F4 -142(2) . . . 2_655 ?
F4 P2 F7 F6 70.1(8) . . . 2_655 ?
F4 P2 F7 F6 -148(3) 2_655 . . 2_655 ?
F6 P2 F4 F7 -28(3) . . . 2_655 ?
F6 P2 F4 F7 120(3) 2_655 . . 2_655 ?
F6 P2 F6 F9 172.9(7) 2_655 . . 2_655 ?
F6 P2 F6 F7 -42.3(8) 2_655 . . 2_655 ?
F6 P2 F8 F5 37.9(13) 2_655 . . 2_655 ?
F6 P2 F8 F5 -172.8(12) . . . 2_655 ?
F6 P2 F8 F9 -32.3(6) . . . 2_655 ?
F6 P2 F8 F9 178.4(8) 2_655 . . 2_655 ?
F6 P2 F5 F8 -145.6(13) . . . 2_655 ?
F6 P2 F5 F8 8.5(15) 2_655 . . 2_655 ?
F6 P2 F5 F9 -172.1(8) 2_655 . . 2_655 ?
F6 P2 F5 F9 33.8(6) . . . 2_655 ?
F6 P2 F9 F8 127.2(9) 2_655 . . 2_655 ?
F6 P2 F9 F5 -124.2(9) 2_655 . . 2_655 ?
F6 P2 F7 F4 148(3) 2_655 . . 2_655 ?
F6 P2 F7 F4 -56(3) . . . 2_655 ?
F6 P2 F7 F6 156.0(6) . . . 2_655 ?
F8 P2 F4 F7 -145(3) 2_655 . . 2_655 ?
F8 P2 F6 F9 43.7(8) . . . 2_655 ?
F8 P2 F6 F9 -64.7(8) 2_655 . . 2_655 ?
F8 P2 F6 F7 -171.4(9) . . . 2_655 ?
F8 P2 F6 F7 80.2(9) 2_655 . . 2_655 ?
F8 P2 F8 F5 -58.7(10) 2_655 . . 2_655 ?
F8 P2 F8 F9 81.8(7) 2_655 . . 2_655 ?
F8 P2 F5 F8 125.3(12) . . . 2_655 ?
F8 P2 F5 F9 179.4(15) 2_655 . . 2_655 ?
F8 P2 F5 F9 -55.3(8) . . . 2_655 ?
F8 P2 F9 F6 123.8(8) . . . 2_655 ?
F8 P2 F9 F6 -127.2(9) 2_655 . . 2_655 ?
F8 P2 F9 F8 -109.0(10) . . . 2_655 ?
F8 P2 F9 F5 -0.3(8) . . . 2_655 ?
F8 P2 F9 F5 108.7(9) 2_655 . . 2_655 ?
F8 P2 F7 F4 32(3) . . . 2_655 ?
F8 P2 F7 F4 164.8(19) 2_655 . . 2_655 ?
F8 P2 F7 F6 17.3(19) 2_655 . . 2_655 ?
F8 P2 F7 F6 -115.0(6) . . . 2_655 ?
F5 P2 F4 F7 -115(3) . . . 2_655 ?
F5 P2 F4 F7 169.7(18) 2_655 . . 2_655 ?
F5 P2 F6 F9 -44.9(8) . . . 2_655 ?
F5 P2 F6 F9 39.1(9) 2_655 . . 2_655 ?
F5 P2 F6 F7 -176.1(9) 2_655 . . 2_655 ?
F5 P2 F6 F7 100.0(9) . . . 2_655 ?
F5 P2 F8 F5 -86.8(13) . . . 2_655 ?
F5 P2 F8 F9 140.5(15) 2_655 . . 2_655 ?
F5 P2 F8 F9 53.7(7) . . . 2_655 ?
F5 P2 F5 F8 91.9(12) 2_655 . . 2_655 ?
F5 P2 F5 F9 -88.7(8) 2_655 . . 2_655 ?
F5 P2 F9 F6 -147.7(7) . . . 2_655 ?
F5 P2 F9 F6 124.2(9) 2_655 . . 2_655 ?
F5 P2 F9 F8 -108.7(9) 2_655 . . 2_655 ?
F5 P2 F9 F8 -20.5(7) . . . 2_655 ?
F5 P2 F9 F5 88.1(10) . . . 2_655 ?
F5 P2 F7 F4 66(3) 2_655 . . 2_655 ?
F5 P2 F7 F6 -81.8(7) 2_655 . . 2_655 ?
F9 P2 F4 F7 158(3) . . . 2_655 ?
F9 P2 F4 F7 -62(3) 2_655 . . 2_655 ?
F9 P2 F6 F7 144.8(10) 2_655 . . 2_655 ?
F9 P2 F8 F5 0.5(13) . . . 2_655 ?
F9 P2 F8 F5 -140.5(15) 2_655 . . 2_655 ?
F9 P2 F8 F9 141.0(10) . . . 2_655 ?
F9 P2 F5 F8 -179.4(15) 2_655 . . 2_655 ?
F9 P2 F5 F8 33.5(13) . . . 2_655 ?
F9 P2 F5 F9 -147.1(9) . . . 2_655 ?
F9 P2 F9 F6 172.7(7) 2_655 . . 2_655 ?
F9 P2 F9 F8 -60.2(6) 2_655 . . 2_655 ?
F9 P2 F9 F5 48.5(5) 2_655 . . 2_655 ?
F9 P2 F7 F4 125(3) . . . 2_655 ?
F9 P2 F7 F4 -25(3) 2_655 . . 2_655 ?
F9 P2 F7 F6 -172.4(8) 2_655 . . 2_655 ?
F9 P2 F7 F6 -23.0(7) . . . 2_655 ?
F7 P2 F4 F7 60(3) . . . 2_655 ?
F7 P2 F6 F9 136.4(9) . . . 2_655 ?
F7 P2 F6 F9 -144.8(10) 2_655 . . 2_655 ?
F7 P2 F6 F7 -78.8(13) . . . 2_655 ?
F7 P2 F8 F5 98.5(13) . . . 2_655 ?
F7 P2 F8 F5 171.9(16) 2_655 . . 2_655 ?
F7 P2 F8 F9 -121.0(9) . . . 2_655 ?
F7 P2 F8 F9 -47.6(19) 2_655 . . 2_655 ?
F7 P2 F5 F8 -84.3(14) 2_655 . . 2_655 ?
F7 P2 F5 F9 95.0(9) 2_655 . . 2_655 ?
F7 P2 F9 F6 30.9(9) . . . 2_655 ?
F7 P2 F9 F6 -51.3(10) 2_655 . . 2_655 ?
F7 P2 F9 F8 158.1(9) . . . 2_655 ?
F7 P2 F9 F8 75.9(10) 2_655 . . 2_655 ?
F7 P2 F9 F5 -175.5(9) 2_655 . . 2_655 ?
F7 P2 F9 F5 -93.2(8) . . . 2_655 ?
F7 P2 F7 F4 -118(3) 2_655 . . 2_655 ?
F7 P2 F7 F6 94.2(9) 2_655 . . 2_655 ?


_olex2_submission_original_sample_id 18AVW014
_olex2_submission_special_instructions 'No special instructions were received'




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

data_Compound4BrPF6
_database_code_depnum_ccdc_archive 'CCDC 2212885'
loop_
_audit_author_name
_audit_author_address
'Nathan L. Kilah'
;University of Tasmania
Australia
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
_audit_creation_date             2020-05-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
# start Validation Reply Form
_vrf_PLAT434_Compound4BrPF6      
;
PROBLEM: Short Inter HL..HL Contact Br2      ..Br3              3.33 Ang.  
RESPONSE: Halogen bond interaction.
;
# end Validation Reply Form
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 Br2 N4, F6 P, Br'
_chemical_formula_sum            'C16 H18 Br3 F6 N4 P'
_chemical_formula_weight         651.04
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.0845(5)
_cell_length_b                   13.9389(5)
_cell_length_c                   12.8043(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.674(2)
_cell_angle_gamma                90
_cell_volume                     2149.64(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      72.23
_cell_measurement_theta_min      4.70
_shelx_estimated_absorpt_T_max   0.790
_shelx_estimated_absorpt_T_min   0.242
_exptl_absorpt_coefficient_mu    8.264
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1112 before and 0.0660 after correction.
The Ratio of minimum to maximum transmission is 0.6400.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.012
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30068
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.330
_diffrn_reflns_theta_min         4.698
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  
'Bruker multilayer X-ray optics (Goebel mirror)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3656
_reflns_number_total             4221
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²+1.9650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0629
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C2(H2), C14(H14), C15(H15), C9(H9), C10(H10), C3(H3)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.42388(2) 0.73725(2) 0.22258(2) 0.02002(8) Uani 1 1 d . . . . .
Br3 Br 0.27363(2) 0.90891(2) 0.32323(2) 0.02197(8) Uani 1 1 d . . . . .
Br1 Br 0.36002(2) 0.17820(2) 0.22885(2) 0.02589(8) Uani 1 1 d . . . . .
P1 P 0.23011(5) 0.27283(5) 0.65712(5) 0.01788(15) Uani 1 1 d . . . . .
F3 F 0.34675(13) 0.29954(12) 0.61407(14) 0.0282(4) Uani 1 1 d . . . . .
F5 F 0.21893(14) 0.18236(12) 0.57928(14) 0.0307(4) Uani 1 1 d . . . . .
F4 F 0.24153(14) 0.36202(12) 0.73475(14) 0.0323(4) Uani 1 1 d . . . . .
F6 F 0.29242(15) 0.20640(13) 0.74556(13) 0.0330(4) Uani 1 1 d . . . . .
F1 F 0.11340(14) 0.24593(13) 0.69966(15) 0.0337(4) Uani 1 1 d . . . . .
F2 F 0.16771(16) 0.33882(13) 0.56841(15) 0.0373(4) Uani 1 1 d . . . . .
N1 N 0.50928(17) 0.11335(15) 0.39411(16) 0.0144(4) Uani 1 1 d . . . . .
N4 N 0.55382(18) 0.62638(16) 0.09128(17) 0.0176(5) Uani 1 1 d . . . . .
N3 N 0.51182(17) 0.54832(15) 0.22929(16) 0.0150(4) Uani 1 1 d . . . . .
N2 N 0.51869(18) 0.02849(15) 0.25323(17) 0.0175(5) Uani 1 1 d . . . . .
C13 C 0.5019(2) 0.63187(18) 0.1791(2) 0.0153(5) Uani 1 1 d . . . . .
C8 C 0.5280(2) 0.44518(18) 0.38521(19) 0.0152(5) Uani 1 1 d . . . . .
C6 C 0.5333(2) 0.28280(18) 0.45115(19) 0.0149(5) Uani 1 1 d . . . . .
C7 C 0.4760(2) 0.35818(18) 0.40065(19) 0.0155(5) Uani 1 1 d . . . . .
H7 H 0.400215 0.350067 0.376336 0.019 Uiso 1 1 calc R U . . .
C1 C 0.4685(2) 0.10211(18) 0.2955(2) 0.0158(5) Uani 1 1 d . . . . .
C11 C 0.6439(2) 0.29481(19) 0.4868(2) 0.0190(5) Uani 1 1 d . . . . .
H11 H 0.683826 0.243469 0.521001 0.023 Uiso 1 1 calc R U . . .
C2 C 0.5893(2) 0.04330(19) 0.4162(2) 0.0200(6) Uani 1 1 d . . . . .
H2 H 0.632131 0.034021 0.480990 0.024 Uiso 1 1 calc R U . . .
C14 C 0.5725(2) 0.4872(2) 0.1710(2) 0.0186(5) Uani 1 1 d . . . . .
H14 H 0.592031 0.422683 0.187999 0.022 Uiso 1 1 calc R U . . .
C15 C 0.5989(2) 0.5361(2) 0.0853(2) 0.0205(6) Uani 1 1 d . . . . .
H15 H 0.640770 0.512518 0.031113 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4652(2) 0.52591(18) 0.3299(2) 0.0166(5) Uani 1 1 d . . . . .
H12A H 0.386096 0.507735 0.316499 0.020 Uiso 1 1 calc R U . . .
H12B H 0.469211 0.583596 0.375154 0.020 Uiso 1 1 calc R U . . .
C9 C 0.6388(2) 0.45705(19) 0.4218(2) 0.0185(5) Uani 1 1 d . . . . .
H9 H 0.674895 0.516521 0.411922 0.022 Uiso 1 1 calc R U . . .
C5 C 0.4766(2) 0.18786(18) 0.4680(2) 0.0181(5) Uani 1 1 d . . . . .
H5A H 0.496078 0.165900 0.540692 0.022 Uiso 1 1 calc R U . . .
H5B H 0.395154 0.196912 0.458914 0.022 Uiso 1 1 calc R U . . .
C10 C 0.6964(2) 0.3824(2) 0.4724(2) 0.0206(6) Uani 1 1 d . . . . .
H10 H 0.771964 0.390791 0.497417 0.025 Uiso 1 1 calc R U . . .
C3 C 0.5946(2) -0.0090(2) 0.3284(2) 0.0209(6) Uani 1 1 d . . . . .
H3 H 0.642138 -0.062252 0.319887 0.025 Uiso 1 1 calc R U . . .
C16 C 0.5656(2) 0.7042(2) 0.0165(2) 0.0275(7) Uani 1 1 d . . . . .
H16A H 0.492176 0.730420 -0.005770 0.041 Uiso 1 1 calc R U . . .
H16B H 0.600083 0.679414 -0.044751 0.041 Uiso 1 1 calc R U . . .
H16C H 0.612340 0.754848 0.049705 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4960(3) -0.0072(2) 0.1460(2) 0.0304(7) Uani 1 1 d . . . . .
H4A H 0.419280 -0.030460 0.136354 0.046 Uiso 1 1 calc R U . . .
H4B H 0.547023 -0.059865 0.133625 0.046 Uiso 1 1 calc R U . . .
H4C H 0.506396 0.044825 0.096263 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 C13 1.855(3) . ?
Br1 C1 1.841(3) . ?
P1 F3 1.5987(16) . ?
P1 F5 1.6062(17) . ?
P1 F4 1.5907(17) . ?
P1 F6 1.6024(18) . ?
P1 F1 1.5974(17) . ?
P1 F2 1.6017(19) . ?
N1 C1 1.327(3) . ?
N1 C2 1.387(3) . ?
N1 C5 1.480(3) . ?
N4 C13 1.334(3) . ?
N4 C15 1.376(4) . ?
N4 C16 1.461(3) . ?
N3 C13 1.331(3) . ?
N3 C14 1.382(3) . ?
N3 C12 1.481(3) . ?
N2 C1 1.329(3) . ?
N2 C3 1.378(4) . ?
N2 C4 1.465(3) . ?
C8 C7 1.387(4) . ?
C8 C12 1.502(3) . ?
C8 C9 1.392(4) . ?
C6 C7 1.388(4) . ?
C6 C11 1.387(4) . ?
C6 C5 1.513(4) . ?
C7 H7 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.395(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.346(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.352(4) . ?
C15 H15 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C10 1.384(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C10 H10 0.9500 . ?
C3 H3 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F3 P1 F5 90.05(9) . . ?
F3 P1 F6 90.09(10) . . ?
F3 P1 F2 89.95(10) . . ?
F4 P1 F3 89.97(9) . . ?
F4 P1 F5 179.65(12) . . ?
F4 P1 F6 89.89(10) . . ?
F4 P1 F1 90.25(10) . . ?
F4 P1 F2 90.36(10) . . ?
F6 P1 F5 89.76(10) . . ?
F1 P1 F3 179.75(11) . . ?
F1 P1 F5 89.73(9) . . ?
F1 P1 F6 90.03(10) . . ?
F1 P1 F2 89.93(11) . . ?
F2 P1 F5 89.99(10) . . ?
F2 P1 F6 179.75(11) . . ?
C1 N1 C2 108.0(2) . . ?
C1 N1 C5 126.4(2) . . ?
C2 N1 C5 125.5(2) . . ?
C13 N4 C15 108.4(2) . . ?
C13 N4 C16 126.0(2) . . ?
C15 N4 C16 125.6(2) . . ?
C13 N3 C14 108.1(2) . . ?
C13 N3 C12 125.4(2) . . ?
C14 N3 C12 126.6(2) . . ?
C1 N2 C3 108.0(2) . . ?
C1 N2 C4 125.9(2) . . ?
C3 N2 C4 126.1(2) . . ?
N4 C13 Br2 125.73(19) . . ?
N3 C13 Br2 125.18(19) . . ?
N3 C13 N4 109.1(2) . . ?
C7 C8 C12 120.3(2) . . ?
C7 C8 C9 119.4(2) . . ?
C9 C8 C12 120.3(2) . . ?
C7 C6 C5 120.9(2) . . ?
C11 C6 C7 119.5(2) . . ?
C11 C6 C5 119.6(2) . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
N1 C1 Br1 124.60(19) . . ?
N1 C1 N2 109.4(2) . . ?
N2 C1 Br1 126.0(2) . . ?
C6 C11 H11 120.0 . . ?
C6 C11 C10 119.9(2) . . ?
C10 C11 H11 120.0 . . ?
N1 C2 H2 126.5 . . ?
C3 C2 N1 106.9(2) . . ?
C3 C2 H2 126.5 . . ?
N3 C14 H14 126.3 . . ?
C15 C14 N3 107.3(2) . . ?
C15 C14 H14 126.3 . . ?
N4 C15 H15 126.4 . . ?
C14 C15 N4 107.2(2) . . ?
C14 C15 H15 126.4 . . ?
N3 C12 C8 110.8(2) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
N1 C5 C6 112.1(2) . . ?
N1 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
N2 C3 H3 126.2 . . ?
C2 C3 N2 107.7(2) . . ?
C2 C3 H3 126.2 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 0.0(3) . . . . ?
N3 C14 C15 N4 -0.4(3) . . . . ?
C13 N4 C15 C14 0.3(3) . . . . ?
C13 N3 C14 C15 0.3(3) . . . . ?
C13 N3 C12 C8 -156.7(2) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C6 C11 C10 C9 -0.6(4) . . . . ?
C7 C8 C12 N3 -114.8(3) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C7 C6 C11 C10 0.4(4) . . . . ?
C7 C6 C5 N1 103.8(3) . . . . ?
C1 N1 C2 C3 0.1(3) . . . . ?
C1 N1 C5 C6 -80.9(3) . . . . ?
C1 N2 C3 C2 -0.1(3) . . . . ?
C11 C6 C7 C8 0.1(4) . . . . ?
C11 C6 C5 N1 -76.4(3) . . . . ?
C2 N1 C1 Br1 -179.76(18) . . . . ?
C2 N1 C1 N2 -0.2(3) . . . . ?
C2 N1 C5 C6 98.4(3) . . . . ?
C14 N3 C13 Br2 178.01(18) . . . . ?
C14 N3 C13 N4 -0.1(3) . . . . ?
C14 N3 C12 C8 23.5(3) . . . . ?
C15 N4 C13 Br2 -178.23(19) . . . . ?
C15 N4 C13 N3 -0.2(3) . . . . ?
C12 N3 C13 Br2 -1.8(4) . . . . ?
C12 N3 C13 N4 -179.9(2) . . . . ?
C12 N3 C14 C15 -179.9(2) . . . . ?
C12 C8 C7 C6 179.7(2) . . . . ?
C12 C8 C9 C10 -179.8(2) . . . . ?
C9 C8 C7 C6 -0.6(4) . . . . ?
C9 C8 C12 N3 65.4(3) . . . . ?
C5 N1 C1 Br1 -0.3(4) . . . . ?
C5 N1 C1 N2 179.3(2) . . . . ?
C5 N1 C2 C3 -179.3(2) . . . . ?
C5 C6 C7 C8 -180.0(2) . . . . ?
C5 C6 C11 C10 -179.4(2) . . . . ?
C3 N2 C1 Br1 179.76(19) . . . . ?
C3 N2 C1 N1 0.2(3) . . . . ?
C16 N4 C13 Br2 4.4(4) . . . . ?
C16 N4 C13 N3 -177.5(2) . . . . ?
C16 N4 C15 C14 177.7(2) . . . . ?
C4 N2 C1 Br1 -1.0(4) . . . . ?
C4 N2 C1 N1 179.4(2) . . . . ?
C4 N2 C3 C2 -179.3(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'



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

data_Compound7PF6
_database_code_depnum_ccdc_archive 'CCDC 2212888'
loop_
_audit_author_name
_audit_author_address
'Nathan L. Kilah'
;University of Tasmania
Australia
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
_audit_creation_date             2020-05-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT088_Compound7PF6        
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.94 Note  
RESPONSE: Crystal has significant disorder. The modeling of this disorder 
has necessitated a number of restraints to remain as reasonable a model as 
possible.
;

_vrf_PLAT215_Compound7PF6        
;
PROBLEM: Disordered C3        has ADP max/min Ratio .....        3.5 Note  
RESPONSE: Crystal has significant disorder. The modeling of this disorder has 
necessitated a number of restraints to remain as reasonable a model as 
possible.
;
_vrf_PLAT244_Compound7PF6        
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of         P1 Check 
RESPONSE: Attempts were made to model this disorder over two positions of 
unequal occupancy, however did not result in a constructive model.
;
_vrf_PLAT250_Compound7PF6        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note  
RESPONSE: Crystal has significant disorder. The modeling of this disorder has 
necessitated a number of restraints to remain as reasonable a model as 
possible.
;



_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 Br N4, F6 P'
_chemical_formula_sum            'C13 H10 Br F6 N4 P'
_chemical_formula_weight         447.13
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   7.7660(6)
_cell_length_b                   16.3478(13)
_cell_length_c                   6.4925(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.324(3)
_cell_angle_gamma                90
_cell_volume                     767.84(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6545
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      74.41
_cell_measurement_theta_min      5.41
_shelx_estimated_absorpt_T_max   0.674
_shelx_estimated_absorpt_T_min   0.414
_exptl_absorpt_coefficient_mu    5.349
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1529 before and 0.1088 after correction.
The Ratio of minimum to maximum transmission is 0.5540.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7226
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.666
_diffrn_reflns_theta_min         5.412
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  
'Bruker multilayer X-ray optics (Goebel mirror)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                768
_reflns_number_total             811
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0  (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'enCIFer (Allen, 1997)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         811
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+11.3642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1544
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N2-C3 = N2-C7
 1.33 with sigma of 0.02
 C3-C4 = C6-C7
 1.38 with sigma of 0.02
 C4-C5 = C5-C6
 1.37 with sigma of 0.02
 C3-C5
 2.36 with sigma of 0.04
 C5-C7
 2.37 with sigma of 0.04
 N2-C6
 2.39 with sigma of 0.04
 C4-C6
 2.35 with sigma of 0.04
 N2-C3 \\sim N2-C7
 with sigma of 0.02
 C3-C4 \\sim C4-C5 \\sim C5-C6 \\sim C6-C7
 with sigma of 0.02
 N2-C6 \\sim N2-C4
 with sigma of 0.04
 C5-C7 \\sim C5-C3 \\sim C6-C4 \\sim C7-C3
 with sigma of 0.04
3. Restrained planarity
 N2, C3, C4, C5, C6, C7
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 2A
C2 \\sim N1 \\sim C1: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
5. Rigid body (RIGU) restrains
 N1, N2, C3, C4, C5, C6, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: Br1(0.25) C2(0.5) H2(0.5) N1(0.5) N2(0.5) C3(0.5) C4(0.5) H4(0.5)
 C5(0.5) H5(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.3595(3) 0.500000 0.6954(4) 0.0277(6) Uani 0.5 2 d S T P A 2
P1 P 1.000000 0.500000 1.000000 0.0178(7) Uani 1 4 d S T P . .
F1 F 0.9752(9) 0.500000 0.7476(9) 0.070(2) Uani 1 2 d S T P . .
F2 F 0.8449(5) 0.4320(2) 0.9496(7) 0.0554(13) Uani 1 1 d . . . . .
C1 C 0.500000 0.500000 0.500000 0.020(2) Uani 1 4 d S TU P . .
C2 C 0.6273(18) 0.5419(11) 0.283(2) 0.034(4) Uani 0.5 1 d . U P A 1
H2 H 0.674004 0.576660 0.197922 0.041 Uiso 0.5 1 calc R U P A 1
N1 N 0.5463(11) 0.5661(5) 0.4301(13) 0.0206(17) Uani 0.5 1 d . U P A .
N2 N 0.488(2) 0.6981(7) 0.291(3) 0.034(3) Uani 0.5 1 d D U P A -1
C3 C 0.5212(18) 0.6517(5) 0.470(2) 0.022(3) Uani 0.5 1 d D U P A -1
C4 C 0.541(2) 0.6795(9) 0.676(3) 0.032(3) Uani 0.5 1 d D U P A -1
H4 H 0.564304 0.642798 0.796387 0.038 Uiso 0.5 1 calc R U P A -1
C5 C 0.525(5) 0.7615(9) 0.703(4) 0.051(6) Uani 0.5 1 d D U P A -1
H5 H 0.535867 0.783053 0.842629 0.061 Uiso 0.5 1 calc R U P A -1
C6 C 0.495(7) 0.8123(6) 0.526(5) 0.049(5) Uani 0.5 1 d D U P A -1
H6 H 0.486750 0.869827 0.541959 0.059 Uiso 0.5 1 calc R U P A -1
C7 C 0.476(5) 0.7789(9) 0.326(4) 0.041(5) Uani 0.5 1 d D U P A -1
H7 H 0.454101 0.814848 0.204217 0.049 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.951(2) . ?
P1 F1 1.579(5) . ?
P1 F1 1.579(5) 5_767 ?
P1 F2 1.583(3) 5_767 ?
P1 F2 1.583(3) . ?
P1 F2 1.583(3) 2_757 ?
P1 F2 1.583(3) 6_565 ?
C1 N1 1.273(8) . ?
C1 N1 1.273(8) 6_565 ?
C1 N1 1.273(8) 2_656 ?
C1 N1 1.273(8) 5_666 ?
C2 H2 0.9500 . ?
C2 N1 1.380(14) . ?
N1 C3 1.449(12) . ?
N2 C3 1.332(11) . ?
N2 C7 1.349(12) . ?
C3 C4 1.367(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.363(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.364(11) . ?
C6 H6 0.9500 . ?
C6 C7 1.368(11) . ?
C7 H7 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 P1 F1 180.0(5) 5_767 . ?
F1 P1 F2 90.6(2) . 2_757 ?
F1 P1 F2 89.4(2) . . ?
F1 P1 F2 89.4(2) . 6_565 ?
F1 P1 F2 90.6(2) 5_767 . ?
F1 P1 F2 90.6(2) 5_767 6_565 ?
F1 P1 F2 89.4(2) 5_767 5_767 ?
F1 P1 F2 89.4(2) 5_767 2_757 ?
F1 P1 F2 90.6(2) . 5_767 ?
F2 P1 F2 89.2(3) 6_565 . ?
F2 P1 F2 90.8(3) 2_757 . ?
F2 P1 F2 89.2(3) 5_767 2_757 ?
F2 P1 F2 180.0 6_565 2_757 ?
F2 P1 F2 90.8(3) 5_767 6_565 ?
F2 P1 F2 180.0 5_767 . ?
N1 C1 Br1 121.9(4) 6_565 . ?
N1 C1 Br1 121.9(4) 5_666 5_666 ?
N1 C1 Br1 121.9(4) 2_656 5_666 ?
N1 C1 Br1 121.9(4) . . ?
N1 C1 N1 180.0 . 5_666 ?
N1 C1 N1 116.1(8) . 6_565 ?
N1 C1 N1 116.1(8) 2_656 5_666 ?
C2 C2 H2 126.7 6_565 . ?
C2 C2 N1 106.6(8) 6_565 . ?
N1 C2 H2 126.7 . . ?
C1 N1 C2 105.3(10) . . ?
C1 N1 C3 133.0(7) . . ?
C2 N1 C3 121.6(10) . . ?
C3 N1 Br1 145.2(6) . 5_666 ?
C3 N2 C7 114.4(13) . . ?
N2 C3 N1 113.0(10) . . ?
N2 C3 C4 125.6(8) . . ?
C4 C3 N1 121.4(10) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.9(12) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(12) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C7 118.7(9) . . ?
C7 C6 H6 120.7 . . ?
N2 C7 C6 124.2(14) . . ?
N2 C7 H7 117.9 . . ?
C6 C7 H7 117.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 N1 Br1 180.000(2) . . . 5_666 ?
Br1 C1 N1 N1 1.9(8) . . . 2_656 ?
Br1 C1 N1 N1 -178.1(8) 5_666 . . 2_656 ?
C1 N1 C3 N2 -143.0(10) . . . . ?
C1 N1 C3 C4 40.2(16) . . . . ?
C2 C2 N1 C1 -1.9(6) 6_565 . . . ?
C2 C2 N1 N1 -12(4) 6_565 . . 2_656 ?
C2 C2 N1 C3 -179.2(9) 6_565 . . . ?
C2 N1 C3 N2 33.4(14) . . . . ?
C2 N1 C3 C4 -143.4(11) . . . . ?
N1 C1 N1 Br1 178.1(8) 2_656 . . 5_666 ?
N1 C1 N1 Br1 -1.9(8) 6_565 . . 5_666 ?
N1 C1 N1 C2 -176.5(12) 2_656 . . . ?
N1 C1 N1 C2 3.5(12) 6_565 . . . ?
N1 C1 N1 N1 180.000(2) 6_565 . . 2_656 ?
N1 C1 N1 C3 0.3(9) 2_656 . . . ?
N1 C1 N1 C3 -179.7(9) 6_565 . . . ?
N1 N1 C3 N2 -142.7(10) 2_656 . . . ?
N1 N1 C3 C4 40.5(11) 2_656 . . . ?
N1 C3 C4 C5 176(2) . . . . ?
N2 C3 C4 C5 0.0(19) . . . . ?
C3 N2 C7 C6 -1(3) . . . . ?
C3 C4 C5 C6 -1(3) . . . . ?
C4 C5 C6 C7 1(5) . . . . ?
C5 C6 C7 N2 -1(5) . . . . ?
C7 N2 C3 N1 -175.7(18) . . . . ?
C7 N2 C3 C4 0.9(17) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'



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

data_Compound1PF62
_database_code_depnum_ccdc_archive 'CCDC 2212890'
loop_
_audit_author_name
_audit_author_address
'Nathan L. Kilah'
;University of Tasmania
Australia
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT213_Compound1PF62       
;
PROBLEM: Atom C25             has ADP max/min Ratio .....        3.5 oblate
RESPONSE: Structure was very disordered. Restraints were applied to control the ADPs, but failed to improve the thermal parameters.
;
_vrf_PLAT213_Compound1PF62_2     
;
PROBLEM: Atom C29             has ADP max/min Ratio .....        3.7 prolat
RESPONSE: Structure was very disordered. Restraints were applied to control the ADPs, but failed to improve the thermal parameters.
;
_vrf_PLAT244_Compound1PF62       
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of         P2 Check
RESPONSE: Structure was very disordered. Restraints were applied to control the ADPs, but failed to improve the thermal parameters.
;
# Added during the CSD deposition process: Friday 14 October 2022 03:06 AM
# end Validation Reply Form

_audit_creation_date             2022-08-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 Br2 N4, 2(F6 P)'
_chemical_formula_sum            'C9 H12 Br2 F12 N4 P2'
_chemical_formula_weight         625.99
_chemical_melting_point          ?
# end Validation Reply Form
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.120(2)
_cell_length_b                   8.5600(17)
_cell_length_c                   19.790(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.33(3)
_cell_angle_gamma                90
_cell_volume                     1883.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    40048
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.183
_cell_measurement_theta_min      2.059
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.803
_exptl_absorpt_coefficient_mu    4.594
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40048
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.183
_diffrn_reflns_theta_min         2.059
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'ADSC Quantum 210r'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_standards_number         ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4237
_reflns_number_total             4641
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         4641
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+1.6865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0874
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H15A(0.038) H15B(0.038) H12(0.032) H13(0.031) H14A(0.049)
 H14B(0.049) H14C(0.049) H17(0.041) H18(0.038) H19A(0.069) H19B(0.069)
 H19C(0.069) H22(0.041) H23(0.036) H24A(0.056) H24B(0.056) H24C(0.056)
 H27(0.033) H28(0.047) H29A(0.082) H29B(0.082) H29C(0.082) H25A(0.036)
 H25B(0.036)
 Fixed X: H15A(0.336558) H15B(0.286036) H12(-0.001975) H13(0.198095) H14A(-
 0.112273) H14B(-0.155674) H14C(-0.079369) H17(0.536851) H18(0.384274)
 H19A(0.647861) H19B(0.676926) H19C(0.57116) H22(0.006514) H23(0.200352) H24A(-
 0.090474) H24B(-0.089455) H24C(-0.158954) H27(0.556273) H28(0.391474)
 H29A(0.567794) H29B(0.672879) H29C(0.6553) H25A(0.340894) H25B(0.28991)
 Fixed Y: H15A(0.475954) H15B(0.471888) H12(0.721282) H13(0.582247)
 H14A(0.789292) H14B(0.778093) H14C(0.925813) H17(0.874055) H18(0.673837)
 H19A(0.922461) H19B(0.969685) H19C(1.056335) H22(0.745997) H23(0.615342)
 H24A(0.846283) H24B(0.922545) H24C(0.761548) H27(0.836206) H28(0.628544)
 H29A(1.060617) H29B(0.985931) H29C(0.931824) H25A(0.495849) H25B(0.474371)
 Fixed Z: H15A(0.594503) H15B(0.669621) H12(0.499034) H13(0.501975)
 H14A(0.665055) H14B(0.587538) H14C(0.61342) H17(0.75078) H18(0.7585)
 H19A(0.580071) H19B(0.656971) H19C(0.615536) H22(0.749109) H23(0.753401)
 H24A(0.576363) H24B(0.650206) H24C(0.63643) H27(0.501153) H28(0.500254)
 H29A(0.637252) H29B(0.593778) H29C(0.670322) H25A(0.665963) H25B(0.590319)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br11 Br 0.10588(5) 0.69326(6) 0.73631(2) 0.02926(13) Uani 0.5466(8) 1 d D . P A
1
Br12 Br 0.46180(5) 0.71563(6) 0.51780(3) 0.03528(15) Uani 0.5466(8) 1 d D . P A
1
Br21 Br 0.10625(6) 0.67666(6) 0.51333(3) 0.03613(17) Uani 0.4534(8) 1 d D . P A
2
Br22 Br 0.45022(6) 0.76632(8) 0.73540(3) 0.02930(15) Uani 0.4534(8) 1 d D . P A
2
N11 N 0.0186(3) 0.7331(4) 0.6025(2) 0.0247(6) Uani 0.5466(8) 1 d D . P A 1
N12 N 0.1898(3) 0.6111(3) 0.60629(19) 0.0231(6) Uani 0.5466(8) 1 d D . P A 1
N13 N 0.3908(3) 0.6616(4) 0.65170(17) 0.0260(6) Uani 0.5466(8) 1 d D . P A 1
N14 N 0.5279(3) 0.8401(4) 0.6451(2) 0.0318(7) Uani 0.5466(8) 1 d D . P A 1
N21 N 0.0196(4) 0.7386(5) 0.6424(3) 0.0322(9) Uani 0.4534(8) 1 d D . P A 2
N22 N 0.1924(4) 0.6237(5) 0.6455(3) 0.0289(8) Uani 0.4534(8) 1 d D . P A 2
N23 N 0.3939(3) 0.6642(4) 0.60273(18) 0.0207(7) Uani 0.4534(8) 1 d D . P A 2
N24 N 0.5326(3) 0.8432(5) 0.6056(3) 0.0277(8) Uani 0.4534(8) 1 d D . P A 2
C15 C 0.3024(8) 0.5409(13) 0.6307(8) 0.032(3) Uani 0.5466(8) 1 d D . P A 1
H15A H 0.336558 0.475954 0.594503 0.038 Uiso 0.5466(8) 1 calc R . P A 1
H15B H 0.286036 0.471888 0.669621 0.038 Uiso 0.5466(8) 1 calc R . P A 1
C11 C 0.1055(3) 0.6793(4) 0.6440(2) 0.0222(7) Uani 0.5466(8) 1 d D . P A 1
C12 C 0.0456(4) 0.6977(5) 0.5382(2) 0.0269(7) Uani 0.5466(8) 1 d D . P A 1
H12 H -0.001975 0.721282 0.499034 0.032 Uiso 0.5466(8) 1 calc R . P A 1
C13 C 0.1555(3) 0.6206(4) 0.53960(19) 0.0257(7) Uani 0.5466(8) 1 d D . P A 1
H13 H 0.198095 0.582247 0.501975 0.031 Uiso 0.5466(8) 1 calc R . P A 1
C14 C -0.0909(12) 0.8129(19) 0.6184(10) 0.033(3) Uani 0.5466(8) 1 d D . P A 1
H14A H -0.112273 0.789292 0.665055 0.049 Uiso 0.5466(8) 1 calc GR . P A 1
H14B H -0.155674 0.778093 0.587538 0.049 Uiso 0.5466(8) 1 calc GR . P A 1
H14C H -0.079369 0.925813 0.613420 0.049 Uiso 0.5466(8) 1 calc GR . P A 1
C16 C 0.4595(4) 0.7416(5) 0.6101(2) 0.0271(9) Uani 0.5466(8) 1 d D . P A 1
C17 C 0.5010(4) 0.8190(6) 0.7138(2) 0.0339(9) Uani 0.5466(8) 1 d D . P A 1
H17 H 0.536851 0.874055 0.750780 0.041 Uiso 0.5466(8) 1 calc R . P A 1
C18 C 0.4188(4) 0.7116(7) 0.7182(2) 0.0313(9) Uani 0.5466(8) 1 d D . P A 1
H18 H 0.384274 0.673837 0.758500 0.038 Uiso 0.5466(8) 1 calc R . P A 1
C19 C 0.6129(10) 0.9566(14) 0.6226(8) 0.046(4) Uani 0.5466(8) 1 d D . P A 1
H19A H 0.647861 0.922461 0.580071 0.069 Uiso 0.5466(8) 1 calc GR . P A 1
H19B H 0.676926 0.969685 0.656971 0.069 Uiso 0.5466(8) 1 calc GR . P A 1
H19C H 0.571160 1.056335 0.615536 0.069 Uiso 0.5466(8) 1 calc GR . P A 1
C21 C 0.1055(4) 0.6810(5) 0.6065(3) 0.0302(11) Uani 0.4534(8) 1 d D . P A 2
C22 C 0.0523(6) 0.7157(6) 0.7114(3) 0.0344(11) Uani 0.4534(8) 1 d D . P A 2
H22 H 0.006514 0.745997 0.749109 0.041 Uiso 0.4534(8) 1 calc R . P A 2
C23 C 0.1565(5) 0.6458(6) 0.7138(3) 0.0302(9) Uani 0.4534(8) 1 d D . P A 2
H23 H 0.200352 0.615342 0.753401 0.036 Uiso 0.4534(8) 1 calc R . P A 2
C24 C -0.0885(13) 0.824(3) 0.6250(13) 0.037(5) Uani 0.4534(8) 1 d D . P A 2
H24A H -0.090474 0.846283 0.576363 0.056 Uiso 0.4534(8) 1 calc GR . P A 2
H24B H -0.089455 0.922545 0.650206 0.056 Uiso 0.4534(8) 1 calc GR . P A 2
H24C H -0.158954 0.761548 0.636430 0.056 Uiso 0.4534(8) 1 calc GR . P A 2
C26 C 0.4591(4) 0.7591(5) 0.6435(3) 0.0216(10) Uani 0.4534(8) 1 d D . P A 2
C27 C 0.5150(4) 0.7975(6) 0.5392(2) 0.0275(9) Uani 0.4534(8) 1 d D . P A 2
H27 H 0.556273 0.836206 0.501153 0.033 Uiso 0.4534(8) 1 calc R . P A 2
C28 C 0.4241(6) 0.6821(8) 0.5385(4) 0.0395(15) Uani 0.4534(8) 1 d D . P A 2
H28 H 0.391474 0.628544 0.500254 0.047 Uiso 0.4534(8) 1 calc R . P A 2
C29 C 0.6137(12) 0.9652(18) 0.6286(11) 0.055(6) Uani 0.4534(8) 1 d D . P A 2
H29A H 0.567794 1.060617 0.637252 0.082 Uiso 0.4534(8) 1 calc GR . P A 2
H29B H 0.672879 0.985931 0.593778 0.082 Uiso 0.4534(8) 1 calc GR . P A 2
H29C H 0.655300 0.931824 0.670322 0.082 Uiso 0.4534(8) 1 calc GR . P A 2
P1 P 0.71056(5) 0.42214(6) 0.65238(3) 0.02761(13) Uani 1 1 d . . . . .
F1 F 0.57095(14) 0.3866(2) 0.64166(12) 0.0687(6) Uani 1 1 d . . . . .
F2 F 0.6813(2) 0.5737(3) 0.69391(10) 0.0750(6) Uani 1 1 d . . . . .
F3 F 0.71543(16) 0.3161(3) 0.71766(8) 0.0633(5) Uani 1 1 d . . . . .
F4 F 0.74125(19) 0.27445(18) 0.60752(9) 0.0592(5) Uani 1 1 d . . . . .
F5 F 0.85077(13) 0.4586(2) 0.66040(10) 0.0589(5) Uani 1 1 d . . . . .
F6 F 0.70463(15) 0.52824(17) 0.58548(7) 0.0468(4) Uani 1 1 d . . . . .
P2 P 0.28013(4) 0.62119(6) 0.90906(2) 0.02301(12) Uani 1 1 d . . . . .
F7 F 0.15106(12) 0.67550(17) 0.87939(8) 0.0422(3) Uani 1 1 d . . . . .
F8 F 0.34237(14) 0.75456(16) 0.86525(7) 0.0431(3) Uani 1 1 d . . . . .
F9 F 0.26693(12) 0.74402(15) 0.96938(6) 0.0323(3) Uani 1 1 d . . . . .
F10 F 0.40763(12) 0.56788(17) 0.93815(8) 0.0423(3) Uani 1 1 d . . . . .
F11 F 0.29274(14) 0.50094(16) 0.84740(7) 0.0428(3) Uani 1 1 d . . . . .
F12 F 0.21640(15) 0.49014(17) 0.95214(8) 0.0505(4) Uani 1 1 d . . . . .
C25 C 0.3061(8) 0.5521(13) 0.6264(10) 0.030(4) Uani 0.4534(8) 1 d D . P A 2
H25A H 0.340894 0.495849 0.665963 0.036 Uiso 0.4534(8) 1 calc R . P A 2
H25B H 0.289910 0.474371 0.590319 0.036 Uiso 0.4534(8) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br11 C11 1.830(5) . ?
Br12 C16 1.842(5) . ?
Br21 C21 1.844(6) . ?
Br22 C26 1.825(5) . ?
N11 C11 1.336(5) . ?
N11 C12 1.349(5) . ?
N11 C14 1.437(11) . ?
N12 C15 1.461(10) . ?
N12 C11 1.345(5) . ?
N12 C13 1.368(5) . ?
N13 C15 1.479(10) . ?
N13 C16 1.326(5) . ?
N13 C18 1.412(6) . ?
N14 C16 1.320(6) . ?
N14 C17 1.411(7) . ?
N14 C19 1.451(10) . ?
N21 C21 1.301(7) . ?
N21 C22 1.417(8) . ?
N21 C24 1.442(12) . ?
N22 C21 1.318(7) . ?
N22 C23 1.430(8) . ?
N22 C25 1.463(10) . ?
N23 C26 1.345(6) . ?
N23 C28 1.331(8) . ?
N23 C25 1.454(11) . ?
N24 C26 1.333(6) . ?
N24 C27 1.381(7) . ?
N24 C29 1.447(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C13 1.389(5) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C17 H17 0.9500 . ?
C17 C18 1.300(7) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.304(8) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C27 H27 0.9500 . ?
C27 C28 1.413(8) . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
P1 F1 1.5914(17) . ?
P1 F2 1.5736(18) . ?
P1 F3 1.5789(16) . ?
P1 F4 1.5864(16) . ?
P1 F5 1.5944(16) . ?
P1 F6 1.6056(15) . ?
P2 F7 1.6068(14) . ?
P2 F8 1.6006(14) . ?
P2 F9 1.6000(13) . ?
P2 F10 1.5849(14) . ?
P2 F11 1.6051(13) . ?
P2 F12 1.5860(15) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N11 C12 109.2(4) . . ?
C11 N11 C14 129.3(9) . . ?
C12 N11 C14 121.4(8) . . ?
C11 N12 C15 126.7(8) . . ?
C11 N12 C13 109.1(3) . . ?
C13 N12 C15 124.2(7) . . ?
C16 N13 C15 125.2(7) . . ?
C16 N13 C18 107.7(4) . . ?
C18 N13 C15 127.2(7) . . ?
C16 N14 C17 106.9(4) . . ?
C16 N14 C19 130.4(8) . . ?
C17 N14 C19 122.6(8) . . ?
C21 N21 C22 107.3(5) . . ?
C21 N21 C24 132.8(11) . . ?
C22 N21 C24 119.7(11) . . ?
C21 N22 C23 106.7(5) . . ?
C21 N22 C25 129.1(9) . . ?
C23 N22 C25 124.1(9) . . ?
C26 N23 C25 124.2(8) . . ?
C28 N23 C26 111.0(5) . . ?
C28 N23 C25 124.8(9) . . ?
C26 N24 C27 107.9(4) . . ?
C26 N24 C29 126.8(9) . . ?
C27 N24 C29 125.3(9) . . ?
N12 C15 N13 111.4(7) . . ?
N12 C15 H15A 109.4 . . ?
N12 C15 H15B 109.4 . . ?
N13 C15 H15A 109.4 . . ?
N13 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N11 C11 Br11 125.2(3) . . ?
N11 C11 N12 108.1(4) . . ?
N12 C11 Br11 126.6(3) . . ?
N11 C12 H12 126.2 . . ?
N11 C12 C13 107.7(3) . . ?
C13 C12 H12 126.2 . . ?
N12 C13 C12 105.8(3) . . ?
N12 C13 H13 127.1 . . ?
C12 C13 H13 127.1 . . ?
N11 C14 H14A 109.5 . . ?
N11 C14 H14B 109.5 . . ?
N11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N13 C16 Br12 125.1(4) . . ?
N14 C16 Br12 125.2(4) . . ?
N14 C16 N13 109.7(5) . . ?
N14 C17 H17 125.7 . . ?
C18 C17 N14 108.6(4) . . ?
C18 C17 H17 125.7 . . ?
N13 C18 H18 126.5 . . ?
C17 C18 N13 107.0(4) . . ?
C17 C18 H18 126.5 . . ?
N14 C19 H19A 109.5 . . ?
N14 C19 H19B 109.5 . . ?
N14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N21 C21 Br21 125.1(5) . . ?
N21 C21 N22 111.0(6) . . ?
N22 C21 Br21 123.9(4) . . ?
N21 C22 H22 126.1 . . ?
C23 C22 N21 107.9(5) . . ?
C23 C22 H22 126.1 . . ?
N22 C23 H23 126.5 . . ?
C22 C23 N22 107.0(4) . . ?
C22 C23 H23 126.5 . . ?
N21 C24 H24A 109.5 . . ?
N21 C24 H24B 109.5 . . ?
N21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N23 C26 Br22 125.2(3) . . ?
N24 C26 Br22 126.2(4) . . ?
N24 C26 N23 108.5(5) . . ?
N24 C27 H27 126.5 . . ?
N24 C27 C28 107.0(4) . . ?
C28 C27 H27 126.5 . . ?
N23 C28 C27 105.5(5) . . ?
N23 C28 H28 127.2 . . ?
C27 C28 H28 127.2 . . ?
N24 C29 H29A 109.5 . . ?
N24 C29 H29B 109.5 . . ?
N24 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
F1 P1 F5 178.04(11) . . ?
F1 P1 F6 88.68(10) . . ?
F2 P1 F1 90.82(12) . . ?
F2 P1 F3 92.88(12) . . ?
F2 P1 F4 177.30(11) . . ?
F2 P1 F5 90.02(12) . . ?
F2 P1 F6 87.68(11) . . ?
F3 P1 F1 90.80(10) . . ?
F3 P1 F4 89.76(11) . . ?
F3 P1 F5 90.93(10) . . ?
F3 P1 F6 179.25(11) . . ?
F4 P1 F1 89.71(12) . . ?
F4 P1 F5 89.37(11) . . ?
F4 P1 F6 89.69(9) . . ?
F5 P1 F6 89.58(9) . . ?
F8 P2 F7 89.40(9) . . ?
F8 P2 F11 89.95(8) . . ?
F9 P2 F7 89.19(8) . . ?
F9 P2 F8 89.07(8) . . ?
F9 P2 F11 178.76(8) . . ?
F10 P2 F7 179.83(10) . . ?
F10 P2 F8 90.44(9) . . ?
F10 P2 F9 90.86(7) . . ?
F10 P2 F11 89.90(8) . . ?
F10 P2 F12 90.47(9) . . ?
F11 P2 F7 90.04(8) . . ?
F12 P2 F7 89.69(9) . . ?
F12 P2 F8 179.08(9) . . ?
F12 P2 F9 90.80(8) . . ?
F12 P2 F11 90.18(9) . . ?
N22 C25 H25A 108.9 . . ?
N22 C25 H25B 108.9 . . ?
N23 C25 N22 113.4(8) . . ?
N23 C25 H25A 108.9 . . ?
N23 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 C12 C13 N12 0.7(4) . . . . ?
N14 C17 C18 N13 -0.3(5) . . . . ?
N21 C22 C23 N22 0.3(5) . . . . ?
N24 C27 C28 N23 -0.6(6) . . . . ?
C15 N12 C11 Br11 -3.4(7) . . . . ?
C15 N12 C11 N11 178.0(6) . . . . ?
C15 N12 C13 C12 -178.7(6) . . . . ?
C15 N13 C16 Br12 -1.6(7) . . . . ?
C15 N13 C16 N14 179.8(6) . . . . ?
C15 N13 C18 C17 180.0(6) . . . . ?
C11 N11 C12 C13 -1.1(4) . . . . ?
C11 N12 C15 N13 -73.7(11) . . . . ?
C11 N12 C13 C12 -0.2(4) . . . . ?
C12 N11 C11 Br11 -177.7(3) . . . . ?
C12 N11 C11 N12 0.9(4) . . . . ?
C13 N12 C15 N13 104.5(10) . . . . ?
C13 N12 C11 Br11 178.1(3) . . . . ?
C13 N12 C11 N11 -0.5(4) . . . . ?
C14 N11 C11 Br11 0.6(10) . . . . ?
C14 N11 C11 N12 179.2(10) . . . . ?
C14 N11 C12 C13 -179.5(9) . . . . ?
C16 N13 C15 N12 -80.5(11) . . . . ?
C16 N13 C18 C17 0.7(5) . . . . ?
C16 N14 C17 C18 -0.3(5) . . . . ?
C17 N14 C16 Br12 -177.9(3) . . . . ?
C17 N14 C16 N13 0.7(4) . . . . ?
C18 N13 C15 N12 100.3(10) . . . . ?
C18 N13 C16 Br12 177.8(3) . . . . ?
C18 N13 C16 N14 -0.9(4) . . . . ?
C19 N14 C16 Br12 4.7(9) . . . . ?
C19 N14 C16 N13 -176.7(7) . . . . ?
C19 N14 C17 C18 177.4(7) . . . . ?
C21 N21 C22 C23 0.1(6) . . . . ?
C21 N22 C23 C22 -0.7(5) . . . . ?
C21 N22 C25 N23 73.9(14) . . . . ?
C22 N21 C21 Br21 178.6(3) . . . . ?
C22 N21 C21 N22 -0.6(5) . . . . ?
C23 N22 C21 Br21 -178.4(3) . . . . ?
C23 N22 C21 N21 0.8(5) . . . . ?
C23 N22 C25 N23 -105.1(12) . . . . ?
C24 N21 C21 Br21 -6.5(15) . . . . ?
C24 N21 C21 N22 174.2(13) . . . . ?
C24 N21 C22 C23 -175.5(11) . . . . ?
C26 N23 C28 C27 -0.2(6) . . . . ?
C26 N23 C25 N22 76.8(13) . . . . ?
C26 N24 C27 C28 1.2(5) . . . . ?
C27 N24 C26 Br22 177.2(3) . . . . ?
C27 N24 C26 N23 -1.4(5) . . . . ?
C28 N23 C26 Br22 -177.5(4) . . . . ?
C28 N23 C26 N24 1.0(5) . . . . ?
C28 N23 C25 N22 -106.3(12) . . . . ?
C29 N24 C26 Br22 -4.9(11) . . . . ?
C29 N24 C26 N23 176.5(9) . . . . ?
C29 N24 C27 C28 -176.7(9) . . . . ?
C25 N22 C21 Br21 2.4(9) . . . . ?
C25 N22 C21 N21 -178.3(7) . . . . ?
C25 N22 C23 C22 178.5(7) . . . . ?
C25 N23 C26 Br22 -0.2(7) . . . . ?
C25 N23 C26 N24 178.3(6) . . . . ?
C25 N23 C28 C27 -177.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT242_Compound1(PF6)2     
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         P2 Check 
RESPONSE: Unknown. Model appears reasonable, and disorder has been modelled for 
one of the hexafluorophosphate anions.
;
####################################################################### 
# 
# 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_Compound5PF62NCMe
_database_code_depnum_ccdc_archive 'CCDC 2212889'
loop_
_audit_author_name
_audit_author_address
'Nathan L. Kilah'
;University of Tasmania
Australia
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
# Added during the CSD deposition process: Friday 14 October 2022 03:05 AM
# end Validation Reply Form

# start Validation Reply Form
_vrf_PLAT029_Compound5PF62NCMe   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.955 Why?
RESPONSE: Crystals diffracted poorly.
;
_vrf_PLAT244_Compound5PF62NCMe   
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of         P1 Check
RESPONSE: Hexafluorophosphate anion is disordered over at least two positions . The thermal parameters of the fluorine atoms are significantly larger than the central phosphorus.
;
_vrf_PLAT244_Compound5PF62NCMe_2 
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of        C30 Check
RESPONSE: The structure contains significant disorder. The thermal parameters of the disorderd hexafluorophosphate anions are significantly larger than those of the more ordered atoms.
;
_vrf_PLAT250_Compound5PF62NCMe   
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note
RESPONSE: The structure contains significant disorder. The thermal parameters of the disorderd hexafluorophosphate anions are signficantly larger than those of the more ordered atoms.
;
_vrf_PLAT250_Compound5PF62NCMe_2 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
RESPONSE: The structure contains significant disorder. The thermal parameters of the disorderd hexafluorophosphate anions are signficantly larger than those of the more ordered atoms.
;
_vrf_PLAT341_Compound5PF62NCMe   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.007 Ang.
RESPONSE: The crystal was quite large, but diffracted poorly at high angle.
;
# Added during the CSD deposition process: Friday 14 October 2022 03:05 AM
# end Validation Reply Form

_audit_creation_date             2020-05-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 Br2 N5, 2(F6 P), C2 H3 N'
_chemical_formula_sum            'C17 H20 Br2 F12 N6 P2'
_chemical_formula_weight         758.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.6098(4)
_cell_length_b                   14.0173(6)
_cell_length_c                   21.5544(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.0030(10)
_cell_angle_gamma                90
_cell_volume                     2595.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9529
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      71.79
_cell_measurement_theta_min      3.76
_shelx_estimated_absorpt_T_max   0.709
_shelx_estimated_absorpt_T_min   0.332
_exptl_absorpt_coefficient_mu    6.153
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.5434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1147 before and 0.0692 after correction.
The Ratio of minimum to maximum transmission is 0.7212.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.941
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41959
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.848
_diffrn_reflns_theta_min         3.764
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  
'Bruker multilayer X-ray optics (Goebel mirror)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4343
_reflns_number_total             4675
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0  (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'enCIFer (Allen, 1997)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.223
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         4675
_refine_ls_number_restraints     152
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.212
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0033P)²+19.1479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1102
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C13
 1.35 with sigma of 0.02
 C12A-C13A
 1.35 with sigma of 0.02
 C21-C22
 1.35 with sigma of 0.02
 C12A-N11A
 1.37 with sigma of 0.02
 N12A-C11A
 1.33 with sigma of 0.02
 C13A-N12A
 1.37 with sigma of 0.02
 C11A-N11A
 1.33 with sigma of 0.02
 N11A-Br1
 2.82 with sigma of 0.04
 N12A-Br1
 2.82 with sigma of 0.04
 Br11-C11 \\sim Br1-C11A
 with sigma of 0.02
 C12-N11 \\sim C12A-N11A
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 N11-C11 \\sim N11A-C11A
 with sigma of 0.02
 N12-C11 \\sim N12A-C11A
 with sigma of 0.02
 N12-C14 \\sim N12A-C14A
 with sigma of 0.02
 N12-C13 \\sim N12A-C13A
 with sigma of 0.02
 N11-C12 \\sim N11A-C12A
 with sigma of 0.02
 C15-N11 \\sim C15-N11A
 with sigma of 0.02
 Br11-N11 \\sim Br1-N11A
 with sigma of 0.04
 Br11-N12 \\sim Br1-N12A
 with sigma of 0.04
 C12-N12 \\sim C12A-N12A
 with sigma of 0.04
 C12-C11 \\sim C12A-C11A
 with sigma of 0.04
 N11-N12 \\sim N11A-N12A
 with sigma of 0.04
 N11-C13 \\sim N11A-C13A
 with sigma of 0.04
 C11-C14 \\sim C11A-C14A
 with sigma of 0.04
 C11-C13 \\sim C11A-C13A
 with sigma of 0.04
 C14-C13 \\sim C14A-C13A
 with sigma of 0.04
 P2-F8 \\sim P2A-F8A
 with sigma of 0.02
 P2-F7 \\sim P2A-F7A
 with sigma of 0.02
 P2-F9 \\sim P2A-F9A
 with sigma of 0.02
 P2-F10 \\sim P2A-F10A
 with sigma of 0.02
 P2-F11 \\sim P2A-F11A
 with sigma of 0.02
 P2-F12 \\sim P2A-F12A
 with sigma of 0.02
 F8-F7 \\sim F8A-F7A
 with sigma of 0.04
 F8-F9 \\sim F8A-F9A
 with sigma of 0.04
 F8-F10 \\sim F8A-F10A
 with sigma of 0.04
 F8-F11 \\sim F8A-F11A
 with sigma of 0.04
 F8-F12 \\sim F8A-F12A
 with sigma of 0.04
 F7-F9 \\sim F7A-F9A
 with sigma of 0.04
 F7-F10 \\sim F7A-F10A
 with sigma of 0.04
 F7-F11 \\sim F7A-F11A
 with sigma of 0.04
 F7-F12 \\sim F7A-F12A
 with sigma of 0.04
 F9-F10 \\sim F9A-F10A
 with sigma of 0.04
 F9-F11 \\sim F9A-F11A
 with sigma of 0.04
 F9-F12 \\sim F9A-F12A
 with sigma of 0.04
 F10-F11 \\sim F10A-F11A
 with sigma of 0.04
 F10-F12 \\sim F10A-F12A
 with sigma of 0.04
 F11-F12 \\sim F11A-F12A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(F12A) \\sim Ueq, Uanis(F8A) \\sim Ueq, Uanis(F7A) \\sim Ueq, Uanis(F10A)
\\sim Ueq, Uanis(F11A) \\sim Ueq, Uanis(F9A) \\sim Ueq, Uanis(P2A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N11A) \\sim Ueq, Uanis(C11A) \\sim Ueq, Uanis(Br1) \\sim Ueq, Uanis(N12A)
\\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C12A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 N11A, C12A, C13A, C14A, N12A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H15C)=Sof(H15D)=Sof(Br1)=Sof(N11A)=Sof(N12A)=Sof(C12A)=Sof(H12A)=
 Sof(C13A)=Sof(H13A)=Sof(C11A)=Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(Br11)=Sof(N11)=Sof(N12)=Sof(C12)=Sof(H12)=Sof(C13)=
 Sof(H13)=Sof(C11)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
 Sof(P2A)=Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(2)
 Sof(P2)=Sof(F7)=Sof(F8)=Sof(F9)=Sof(F10)=Sof(F11)=Sof(F12)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C15(H15C,H15D)
6.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C3(H3), C21(H21), C22(H22), C12(H12), C13(H13),
 C12A(H12A), C13A(H13A)
6.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C14(H14A,H14B,H14C), C14A(H14D,H14E,H14F), C31(H31A,H31B,
 H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.02172(6) 0.84590(4) 0.74888(2) 0.02695(16) Uani 1 1 d . . . . .
N13 N 0.1374(4) 0.8586(3) 0.55519(18) 0.0158(8) Uani 1 1 d . . . . .
N15 N 0.1276(5) 0.6629(3) 0.71484(18) 0.0194(9) Uani 1 1 d . . . . .
N14 N -0.0055(4) 0.7344(3) 0.63941(18) 0.0152(8) Uani 1 1 d . . . . .
C7 C -0.0933(5) 0.8085(3) 0.6036(2) 0.0170(10) Uani 1 1 d . . . . .
H7A H -0.174099 0.835317 0.629084 0.020 Uiso 1 1 calc R U . . .
H7B H -0.146099 0.779672 0.565888 0.020 Uiso 1 1 calc R U . . .
C19 C 0.0138(5) 0.8875(3) 0.5850(2) 0.0154(9) Uani 1 1 d . . . . .
C16 C 0.2350(5) 0.9249(3) 0.5376(2) 0.0150(9) Uani 1 1 d . . . . .
C17 C 0.2147(6) 1.0221(3) 0.5487(2) 0.0190(10) Uani 1 1 d . . . . .
H17 H 0.287194 1.067595 0.535454 0.023 Uiso 1 1 calc R U . . .
C18 C 0.0882(6) 1.0502(4) 0.5790(2) 0.0212(11) Uani 1 1 d . . . . .
H18 H 0.071322 1.115879 0.587132 0.025 Uiso 1 1 calc R U . . .
C3 C -0.0154(6) 0.9819(3) 0.5978(2) 0.0178(10) Uani 1 1 d . . . . .
H3 H -0.104179 0.999720 0.618943 0.021 Uiso 1 1 calc R U . . .
C15 C 0.3751(6) 0.8906(3) 0.5048(2) 0.0195(10) Uani 1 1 d D . . . .
H15A H 0.371616 0.917833 0.462389 0.023 Uiso 0.869(2) 1 calc R U P A 1
H15B H 0.471769 0.913077 0.527829 0.023 Uiso 0.869(2) 1 calc R U P A 1
H15C H 0.420122 0.945658 0.483633 0.023 Uiso 0.131(2) 1 calc R U P A 2
H15D H 0.454818 0.867428 0.536635 0.023 Uiso 0.131(2) 1 calc R U P A 2
C21 C 0.0411(6) 0.6469(3) 0.6172(2) 0.0196(10) Uani 1 1 d D . . . .
H21 H 0.018904 0.622997 0.576274 0.023 Uiso 1 1 calc R U . . .
C20 C 0.0486(5) 0.7420(4) 0.6986(2) 0.0189(10) Uani 1 1 d . . . . .
C22 C 0.1214(5) 0.6030(3) 0.6628(2) 0.0203(11) Uani 1 1 d D . . . .
H22 H 0.167143 0.541443 0.660784 0.024 Uiso 1 1 calc R U . . .
C23 C 0.1964(6) 0.6414(4) 0.7777(2) 0.0279(12) Uani 1 1 d . . . . .
H23A H 0.254608 0.697007 0.794186 0.042 Uiso 1 1 calc R U . . .
H23B H 0.266988 0.586782 0.775825 0.042 Uiso 1 1 calc R U . . .
H23C H 0.113400 0.626029 0.804942 0.042 Uiso 1 1 calc R U . . .
Br11 Br 0.25904(7) 0.78197(5) 0.37521(3) 0.0189(2) Uani 0.869(2) 1 d D . P A 1
N11 N 0.3772(5) 0.7854(3) 0.5010(2) 0.0144(9) Uani 0.869(2) 1 d D . P A 1
N12 N 0.3230(5) 0.6424(3) 0.4677(2) 0.0170(10) Uani 0.869(2) 1 d D . P A 1
C12 C 0.4128(14) 0.7245(6) 0.5501(5) 0.020(2) Uani 0.869(2) 1 d D . P A 1
H12 H 0.453085 0.741938 0.590704 0.023 Uiso 0.869(2) 1 calc R U P A 1
C13 C 0.3789(7) 0.6344(5) 0.5293(3) 0.0218(13) Uani 0.869(2) 1 d D . P A 1
H13 H 0.391326 0.577130 0.552629 0.026 Uiso 0.869(2) 1 calc R U P A 1
C11 C 0.3218(6) 0.7340(4) 0.4522(2) 0.0127(11) Uani 0.869(2) 1 d D . P A 1
C14 C 0.2753(15) 0.5629(4) 0.4260(5) 0.0241(18) Uani 0.869(2) 1 d D . P A 1
H14A H 0.168098 0.573093 0.408982 0.036 Uiso 0.869(2) 1 calc R U P A 1
H14B H 0.281484 0.502908 0.449399 0.036 Uiso 0.869(2) 1 calc R U P A 1
H14C H 0.344715 0.559740 0.391903 0.036 Uiso 0.869(2) 1 calc R U P A 1
Br1 Br 0.4192(11) 0.6899(6) 0.5589(4) 0.032(2) Uani 0.131(2) 1 d D U P A 2
N11A N 0.343(3) 0.8130(12) 0.4581(8) 0.018(6) Uani 0.131(2) 1 d D U P A 2
N12A N 0.295(4) 0.6639(15) 0.4360(10) 0.023(7) Uani 0.131(2) 1 d D U P A 2
C12A C 0.292(4) 0.8083(19) 0.3968(10) 0.013(6) Uani 0.131(2) 1 d D U P A 2
H12A H 0.282867 0.860503 0.368620 0.015 Uiso 0.131(2) 1 calc R U P A 2
C13A C 0.255(4) 0.7159(19) 0.3829(11) 0.022(6) Uani 0.131(2) 1 d D U P A 2
H13A H 0.211207 0.692007 0.344354 0.026 Uiso 0.131(2) 1 calc R U P A 2
C11A C 0.340(4) 0.7249(15) 0.4809(9) 0.016(10) Uani 0.131(2) 1 d D U P A 2
C14A C 0.288(13) 0.5598(19) 0.443(3) 0.032(15) Uani 0.131(2) 1 d D U P A 2
H14D H 0.313964 0.542964 0.486910 0.048 Uiso 0.131(2) 1 calc R U P A 2
H14E H 0.362556 0.529593 0.417118 0.048 Uiso 0.131(2) 1 calc R U P A 2
H14F H 0.182621 0.537336 0.430712 0.048 Uiso 0.131(2) 1 calc R U P A 2
P1 P 0.20660(14) 0.34953(8) 0.56884(5) 0.0152(3) Uani 1 1 d . . . . .
F1 F 0.2600(4) 0.3505(2) 0.49956(15) 0.0369(8) Uani 1 1 d . . . . .
F2 F 0.0523(4) 0.2939(2) 0.54476(15) 0.0330(8) Uani 1 1 d . . . . .
F3 F 0.1513(4) 0.3495(3) 0.63782(14) 0.0442(9) Uani 1 1 d . . . . .
F4 F 0.3608(4) 0.4057(2) 0.59175(18) 0.0417(9) Uani 1 1 d . . . . .
F5 F 0.1190(4) 0.4492(2) 0.55556(16) 0.0351(8) Uani 1 1 d . . . . .
F6 F 0.2951(4) 0.2507(2) 0.58195(17) 0.0372(8) Uani 1 1 d . . . . .
N30 N 0.9185(5) 0.4539(4) 0.8667(2) 0.0323(11) Uani 1 1 d . . . . .
P2 P 0.6201(6) 0.6181(3) 0.7093(2) 0.0163(10) Uani 0.773(9) 1 d D . P B 1
F7 F 0.4765(5) 0.6895(4) 0.6968(2) 0.0285(12) Uani 0.773(9) 1 d D . P B 1
F8 F 0.6696(7) 0.6351(4) 0.6403(2) 0.0219(12) Uani 0.773(9) 1 d D . P B 1
F9 F 0.7600(6) 0.5448(5) 0.7210(2) 0.056(2) Uani 0.773(9) 1 d D . P B 1
F10 F 0.5711(8) 0.6011(5) 0.7785(2) 0.0303(14) Uani 0.773(9) 1 d D . P B 1
F11 F 0.5076(6) 0.5330(3) 0.6856(2) 0.0356(14) Uani 0.773(9) 1 d D . P B 1
F12 F 0.7282(7) 0.7043(5) 0.7330(2) 0.0476(19) Uani 0.773(9) 1 d D . P B 1
P2A P 0.6373(17) 0.6254(11) 0.7144(8) 0.033(6) Uani 0.227(9) 1 d D U P B 2
F7A F 0.4653(17) 0.633(2) 0.6810(9) 0.063(7) Uani 0.227(9) 1 d D U P B 2
F8A F 0.709(3) 0.607(2) 0.6490(10) 0.067(10) Uani 0.227(9) 1 d D U P B 2
F9A F 0.8072(13) 0.6162(12) 0.7476(6) 0.030(4) Uani 0.227(9) 1 d D U P B 2
F10A F 0.567(3) 0.6441(19) 0.7795(9) 0.055(8) Uani 0.227(9) 1 d D U P B 2
F11A F 0.611(3) 0.5143(11) 0.7196(13) 0.082(8) Uani 0.227(9) 1 d D U P B 2
F12A F 0.664(3) 0.7353(11) 0.7058(14) 0.074(7) Uani 0.227(9) 1 d D U P B 2
C30 C 0.9546(7) 0.4307(4) 0.8195(3) 0.0335(14) Uani 1 1 d . . . C 1
C31 C 0.9994(12) 0.4012(5) 0.7579(4) 0.072(3) Uani 1 1 d . . . . .
H31A H 0.975343 0.452515 0.727858 0.108 Uiso 1 1 calc R U . C 1
H31B H 0.941368 0.343641 0.744692 0.108 Uiso 1 1 calc R U . C 1
H31C H 1.111289 0.387635 0.759895 0.108 Uiso 1 1 calc R U . C 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 C20 1.840(5) . ?
N13 C19 1.343(6) . ?
N13 C16 1.326(6) . ?
N15 C20 1.334(7) . ?
N15 C22 1.400(6) . ?
N15 C23 1.472(6) . ?
N14 C7 1.470(6) . ?
N14 C21 1.386(6) . ?
N14 C20 1.331(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C19 1.513(6) . ?
C19 C3 1.378(7) . ?
C16 C17 1.396(7) . ?
C16 C15 1.519(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.367(7) . ?
C18 H18 0.9500 . ?
C18 C3 1.389(7) . ?
C3 H3 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 H15C 0.9900 . ?
C15 H15D 0.9900 . ?
C15 N11 1.476(7) . ?
C15 N11A 1.495(16) . ?
C21 H21 0.9500 . ?
C21 C22 1.316(7) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
Br11 C11 1.836(5) . ?
N11 C12 1.378(10) . ?
N11 C11 1.335(7) . ?
N12 C13 1.385(8) . ?
N12 C11 1.326(7) . ?
N12 C14 1.471(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.365(11) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
Br1 C11A 1.836(15) . ?
N11A C12A 1.365(15) . ?
N11A C11A 1.331(14) . ?
N12A C13A 1.380(14) . ?
N12A C11A 1.330(14) . ?
N12A C14A 1.469(19) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.361(15) . ?
C13A H13A 0.9500 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
P1 F1 1.593(3) . ?
P1 F2 1.596(3) . ?
P1 F3 1.593(3) . ?
P1 F4 1.592(3) . ?
P1 F5 1.604(3) . ?
P1 F6 1.597(3) . ?
N30 C30 1.133(8) . ?
P2 F7 1.599(5) . ?
P2 F8 1.593(5) . ?
P2 F9 1.590(6) . ?
P2 F10 1.597(5) . ?
P2 F11 1.598(6) . ?
P2 F12 1.588(6) . ?
P2A F7A 1.603(15) . ?
P2A F8A 1.597(15) . ?
P2A F9A 1.588(15) . ?
P2A F10A 1.588(15) . ?
P2A F11A 1.579(15) . ?
P2A F12A 1.570(16) . ?
C30 C31 1.468(9) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N13 C19 117.6(4) . . ?
C20 N15 C22 107.4(4) . . ?
C20 N15 C23 125.3(4) . . ?
C22 N15 C23 127.2(4) . . ?
C21 N14 C7 126.4(4) . . ?
C20 N14 C7 125.4(4) . . ?
C20 N14 C21 108.1(4) . . ?
N14 C7 H7A 109.5 . . ?
N14 C7 H7B 109.5 . . ?
N14 C7 C19 110.8(4) . . ?
H7A C7 H7B 108.1 . . ?
C19 C7 H7A 109.5 . . ?
C19 C7 H7B 109.5 . . ?
N13 C19 C7 115.1(4) . . ?
N13 C19 C3 123.2(4) . . ?
C3 C19 C7 121.8(4) . . ?
N13 C16 C17 123.1(4) . . ?
N13 C16 C15 116.8(4) . . ?
C17 C16 C15 120.1(4) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 C16 118.5(5) . . ?
C18 C17 H17 120.8 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C3 119.4(5) . . ?
C3 C18 H18 120.3 . . ?
C19 C3 C18 118.3(5) . . ?
C19 C3 H3 120.9 . . ?
C18 C3 H3 120.9 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 108.5 . . ?
C16 C15 H15D 108.5 . . ?
H15A C15 H15B 108.1 . . ?
H15C C15 H15D 107.5 . . ?
N11 C15 C16 110.8(4) . . ?
N11 C15 H15A 109.5 . . ?
N11 C15 H15B 109.5 . . ?
N11A C15 C16 115.3(12) . . ?
N11A C15 H15C 108.5 . . ?
N11A C15 H15D 108.5 . . ?
N14 C21 H21 126.1 . . ?
C22 C21 N14 107.8(4) . . ?
C22 C21 H21 126.1 . . ?
N15 C20 Br2 125.9(4) . . ?
N14 C20 Br2 125.2(4) . . ?
N14 C20 N15 108.9(4) . . ?
N15 C22 H22 126.1 . . ?
C21 C22 N15 107.8(4) . . ?
C21 C22 H22 126.1 . . ?
N15 C23 H23A 109.5 . . ?
N15 C23 H23B 109.5 . . ?
N15 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12 N11 C15 125.3(6) . . ?
C11 N11 C15 125.3(4) . . ?
C11 N11 C12 108.6(6) . . ?
C13 N12 C14 126.0(6) . . ?
C11 N12 C13 108.4(5) . . ?
C11 N12 C14 125.6(5) . . ?
N11 C12 H12 126.6 . . ?
C13 C12 N11 106.8(7) . . ?
C13 C12 H12 126.6 . . ?
N12 C13 H13 126.5 . . ?
C12 C13 N12 107.0(5) . . ?
C12 C13 H13 126.5 . . ?
N11 C11 Br11 125.5(4) . . ?
N12 C11 Br11 125.3(4) . . ?
N12 C11 N11 109.1(5) . . ?
N12 C14 H14A 109.5 . . ?
N12 C14 H14B 109.5 . . ?
N12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12A N11A C15 136.1(17) . . ?
C11A N11A C15 115.7(15) . . ?
C11A N11A C12A 107.5(15) . . ?
C13A N12A C14A 127(2) . . ?
C11A N12A C13A 107.9(15) . . ?
C11A N12A C14A 125(2) . . ?
N11A C12A H12A 125.9 . . ?
C13A C12A N11A 108.2(16) . . ?
C13A C12A H12A 125.9 . . ?
N12A C13A H13A 126.8 . . ?
C12A C13A N12A 106.4(17) . . ?
C12A C13A H13A 126.8 . . ?
N11A C11A Br1 124.9(15) . . ?
N12A C11A Br1 124.5(15) . . ?
N12A C11A N11A 109.9(14) . . ?
N12A C14A H14D 109.5 . . ?
N12A C14A H14E 109.5 . . ?
N12A C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
F1 P1 F2 89.31(18) . . ?
F1 P1 F5 89.32(19) . . ?
F1 P1 F6 90.46(19) . . ?
F2 P1 F5 89.84(18) . . ?
F2 P1 F6 90.59(18) . . ?
F3 P1 F1 179.2(2) . . ?
F3 P1 F2 90.4(2) . . ?
F3 P1 F5 89.97(19) . . ?
F3 P1 F6 90.3(2) . . ?
F4 P1 F1 89.8(2) . . ?
F4 P1 F2 179.1(2) . . ?
F4 P1 F3 90.5(2) . . ?
F4 P1 F5 89.77(19) . . ?
F4 P1 F6 89.80(19) . . ?
F6 P1 F5 179.5(2) . . ?
F8 P2 F7 90.2(3) . . ?
F8 P2 F10 179.8(5) . . ?
F8 P2 F11 90.5(4) . . ?
F9 P2 F7 178.4(5) . . ?
F9 P2 F8 89.7(3) . . ?
F9 P2 F10 90.1(4) . . ?
F9 P2 F11 90.2(4) . . ?
F10 P2 F7 90.0(3) . . ?
F10 P2 F11 89.6(3) . . ?
F11 P2 F7 88.2(4) . . ?
F12 P2 F7 90.4(4) . . ?
F12 P2 F8 89.9(3) . . ?
F12 P2 F9 91.1(5) . . ?
F12 P2 F10 90.0(4) . . ?
F12 P2 F11 178.6(4) . . ?
F8A P2A F7A 90.7(13) . . ?
F9A P2A F7A 178.9(15) . . ?
F9A P2A F8A 89.2(13) . . ?
F9A P2A F10A 90.8(12) . . ?
F10A P2A F7A 89.3(13) . . ?
F10A P2A F8A 179.6(16) . . ?
F11A P2A F7A 87.6(13) . . ?
F11A P2A F8A 88.5(13) . . ?
F11A P2A F9A 91.3(12) . . ?
F11A P2A F10A 91.9(13) . . ?
F12A P2A F7A 91.4(13) . . ?
F12A P2A F8A 88.9(13) . . ?
F12A P2A F9A 89.7(12) . . ?
F12A P2A F10A 90.7(14) . . ?
F12A P2A F11A 177.2(16) . . ?
N30 C30 C31 179.2(8) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N13 C19 C3 C18 -0.1(7) . . . . ?
N13 C16 C17 C18 -0.1(7) . . . . ?
N13 C16 C15 N11 -2.0(6) . . . . ?
N13 C16 C15 N11A 41.8(10) . . . . ?
N14 C7 C19 N13 53.1(5) . . . . ?
N14 C7 C19 C3 -127.1(5) . . . . ?
N14 C21 C22 N15 -0.4(5) . . . . ?
C7 N14 C21 C22 177.7(4) . . . . ?
C7 N14 C20 Br2 1.3(7) . . . . ?
C7 N14 C20 N15 -177.5(4) . . . . ?
C7 C19 C3 C18 -179.8(4) . . . . ?
C19 N13 C16 C17 0.0(7) . . . . ?
C19 N13 C16 C15 179.1(4) . . . . ?
C16 N13 C19 C7 179.8(4) . . . . ?
C16 N13 C19 C3 0.1(7) . . . . ?
C16 C17 C18 C3 0.1(7) . . . . ?
C16 C15 N11 C12 -72.8(8) . . . . ?
C16 C15 N11 C11 96.0(6) . . . . ?
C16 C15 N11A C12A 85(4) . . . . ?
C16 C15 N11A C11A -83(3) . . . . ?
C17 C16 C15 N11 177.1(4) . . . . ?
C17 C16 C15 N11A -139.0(9) . . . . ?
C17 C18 C3 C19 0.0(7) . . . . ?
C15 C16 C17 C18 -179.2(4) . . . . ?
C15 N11 C12 C13 171.1(6) . . . . ?
C15 N11 C11 Br11 10.1(8) . . . . ?
C15 N11 C11 N12 -171.5(5) . . . . ?
C15 N11A C12A C13A -168(3) . . . . ?
C15 N11A C11A Br1 -16(5) . . . . ?
C15 N11A C11A N12A 174(3) . . . . ?
C21 N14 C7 C19 -101.4(5) . . . . ?
C21 N14 C20 Br2 178.8(3) . . . . ?
C21 N14 C20 N15 0.0(5) . . . . ?
C20 N15 C22 C21 0.4(5) . . . . ?
C20 N14 C7 C19 75.7(6) . . . . ?
C20 N14 C21 C22 0.2(5) . . . . ?
C22 N15 C20 Br2 -179.0(3) . . . . ?
C22 N15 C20 N14 -0.2(5) . . . . ?
C23 N15 C20 Br2 5.5(7) . . . . ?
C23 N15 C20 N14 -175.7(4) . . . . ?
C23 N15 C22 C21 175.8(5) . . . . ?
N11 C12 C13 N12 -0.1(10) . . . . ?
C12 N11 C11 Br11 -179.5(6) . . . . ?
C12 N11 C11 N12 -1.1(8) . . . . ?
C13 N12 C11 Br11 179.5(4) . . . . ?
C13 N12 C11 N11 1.1(6) . . . . ?
C11 N11 C12 C13 0.7(10) . . . . ?
C11 N12 C13 C12 -0.6(8) . . . . ?
C14 N12 C13 C12 178.5(9) . . . . ?
C14 N12 C11 Br11 0.4(10) . . . . ?
C14 N12 C11 N11 -178.0(7) . . . . ?
N11A C12A C13A N12A -4(4) . . . . ?
C12A N11A C11A Br1 173(3) . . . . ?
C12A N11A C11A N12A 2(4) . . . . ?
C13A N12A C11A Br1 -175(3) . . . . ?
C13A N12A C11A N11A -5(5) . . . . ?
C11A N11A C12A C13A 1(4) . . . . ?
C11A N12A C13A C12A 5(4) . . . . ?
C14A N12A C13A C12A -176(6) . . . . ?
C14A N12A C11A Br1 5(8) . . . . ?
C14A N12A C11A N11A 176(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'



