# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Br2F8bph
_database_code_depnum_ccdc_archive 'CCDC 2092652'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-06-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'Br2 C12 F8'
_chemical_formula_sum            'Br2 C12 F8'
_chemical_formula_weight         455.928
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.2078(10)
_cell_length_b                   7.3883(5)
_cell_length_c                   13.6241(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.544(3)
_cell_angle_gamma                90
_cell_volume                     1244.93(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9118
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.304
_cell_measurement_theta_min      2.666
_exptl_absorpt_coefficient_mu    6.602
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1120 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.5430.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.433
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             855.112
_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.304
_exptl_crystal_size_min          0.256
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23306
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9997
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.67
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9997
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -17
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -9
_reflns_number_gt                2621
_reflns_number_total             2968
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.5250
_refine_diff_density_min         -0.5530
_refine_diff_density_rms         0.1114
_refine_ls_d_res_high            0.7600
_refine_ls_d_res_low             7.6405
_refine_ls_goodness_of_fit_ref   1.0562
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0222
_refine_ls_restrained_S_all      1.0562
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0149P)²+1.0532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0459
_refine_ls_wR_factor_ref         0.0490
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br1 Br 0.66022(2) 0.65255(3) 0.712121(17) 0.02315(7) Uani 1.000000 .
Br2 Br 0.51098(2) 0.74654(3) -0.121465(16) 0.02148(6) Uani 1.000000 .
F1 F 0.70754(11) 0.5947(2) 0.05046(11) 0.0256(3) Uani 1.000000 .
F2 F 0.74957(11) 0.5779(2) 0.25747(10) 0.0249(3) Uani 1.000000 .
F3 F 0.40675(11) 0.82774(19) 0.20742(10) 0.0225(3) Uani 1.000000 .
F4 F 0.36715(11) 0.85220(19) 0.00168(10) 0.0247(3) Uani 1.000000 .
F5 F 0.61340(11) 0.98478(17) 0.57049(10) 0.0224(3) Uani 1.000000 .
F6 F 0.57431(11) 1.00555(16) 0.36446(10) 0.0191(3) Uani 1.000000 .
F7 F 0.62915(12) 0.37673(17) 0.35385(10) 0.0234(3) Uani 1.000000 .
F8 F 0.66208(13) 0.35334(18) 0.55845(10) 0.0277(3) Uani 1.000000 .
C1 C 0.63690(18) 0.6684(3) 0.56890(16) 0.0170(4) Uani 1.000000 .
C2 C 0.61551(18) 0.8333(3) 0.51757(17) 0.0168(4) Uani 1.000000 .
C3 C 0.59636(17) 0.8441(3) 0.41153(16) 0.0149(4) Uani 1.000000 .
C4 C 0.60074(18) 0.6922(3) 0.35307(16) 0.0152(4) Uani 1.000000 .
C5 C 0.62422(18) 0.5283(3) 0.40624(16) 0.0167(4) Uani 1.000000 .
C6 C 0.64157(18) 0.5157(3) 0.51198(17) 0.0181(4) Uani 1.000000 .
C7 C 0.53772(18) 0.7279(3) 0.02209(16) 0.0164(4) Uani 1.000000 .
C8 C 0.63403(18) 0.6572(3) 0.08908(17) 0.0170(4) Uani 1.000000 .
C9 C 0.65483(17) 0.6468(3) 0.19549(16) 0.0165(4) Uani 1.000000 .
C10 C 0.57989(18) 0.7043(3) 0.23911(16) 0.0140(4) Uani 1.000000 .
C11 C 0.48316(17) 0.7728(3) 0.17071(17) 0.0158(4) Uani 1.000000 .
C12 C 0.46202(18) 0.7849(3) 0.06415(17) 0.0174(4) Uani 1.000000 .


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 1.869(2) . ?
Br2 C7 1.867(2) . ?
F1 C8 1.339(2) . ?
F2 C9 1.340(2) . ?
F3 C11 1.337(2) . ?
F4 C12 1.339(2) . ?
F5 C2 1.337(2) . ?
F6 C3 1.337(2) . ?
F7 C5 1.342(2) . ?
F8 C6 1.339(2) . ?
C1 C2 1.384(3) . ?
C1 C6 1.383(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.389(3) . ?
C4 C10 1.481(3) . ?
C5 C6 1.380(3) . ?
C7 C8 1.382(3) . ?
C7 C12 1.381(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.382(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 120.82(17) . . ?
C6 C1 Br1 120.72(17) . . ?
C6 C1 C2 118.46(19) . . ?
C1 C2 F5 120.25(19) . . ?
C3 C2 F5 119.09(19) . . ?
C3 C2 C1 120.7(2) . . ?
C2 C3 F6 118.86(19) . . ?
C4 C3 F6 119.45(18) . . ?
C4 C3 C2 121.68(19) . . ?
C5 C4 C3 116.86(19) . . ?
C10 C4 C3 121.48(19) . . ?
C10 C4 C5 121.66(19) . . ?
C4 C5 F7 119.59(18) . . ?
C6 C5 F7 118.50(19) . . ?
C6 C5 C4 121.9(2) . . ?
C1 C6 F8 120.49(19) . . ?
C5 C6 F8 119.1(2) . . ?
C5 C6 C1 120.4(2) . . ?
C8 C7 Br2 120.78(17) . . ?
C12 C7 Br2 120.92(17) . . ?
C12 C7 C8 118.29(19) . . ?
C7 C8 F1 119.84(19) . . ?
C9 C8 F1 119.31(19) . . ?
C9 C8 C7 120.8(2) . . ?
C8 C9 F2 118.73(19) . . ?
C10 C9 F2 119.66(19) . . ?
C10 C9 C8 121.6(2) . . ?
C9 C10 C4 122.15(19) . . ?
C11 C10 C4 121.0(2) . . ?
C11 C10 C9 116.84(19) . . ?
C10 C11 F3 119.87(19) . . ?
C12 C11 F3 118.20(19) . . ?
C12 C11 C10 121.9(2) . . ?
C7 C12 F4 120.12(19) . . ?
C11 C12 F4 119.4(2) . . ?
C11 C12 C7 120.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 F5 1.4(2) . . . . ?
Br1 C1 C2 C3 -178.79(17) . . . . ?
Br1 C1 C6 F8 0.5(2) . . . . ?
Br1 C1 C6 C5 179.97(17) . . . . ?
Br2 C7 C8 F1 -2.61(19) . . . . ?
Br2 C7 C8 C9 178.64(17) . . . . ?
Br2 C7 C12 F4 1.02(19) . . . . ?
Br2 C7 C12 C11 -179.15(17) . . . . ?
F1 C8 C7 C12 177.6(2) . . . . ?
F1 C8 C9 F2 1.5(2) . . . . ?
F1 C8 C9 C10 -177.88(19) . . . . ?
F2 C9 C8 C7 -179.73(19) . . . . ?
F2 C9 C10 C4 -0.0(2) . . . . ?
F2 C9 C10 C11 -179.4(2) . . . . ?
F3 C11 C10 C4 -0.5(2) . . . . ?
F3 C11 C10 C9 178.90(19) . . . . ?
F3 C11 C12 F4 0.6(2) . . . . ?
F3 C11 C12 C7 -179.21(19) . . . . ?
F4 C12 C7 C8 -179.2(2) . . . . ?
F4 C12 C11 C10 179.98(19) . . . . ?
F5 C2 C1 C6 -178.1(2) . . . . ?
F5 C2 C3 F6 -1.2(2) . . . . ?
F5 C2 C3 C4 178.01(19) . . . . ?
F6 C3 C2 C1 178.96(19) . . . . ?
F6 C3 C4 C5 179.9(2) . . . . ?
F6 C3 C4 C10 -0.9(2) . . . . ?
F7 C5 C4 C3 179.7(2) . . . . ?
F7 C5 C4 C10 0.5(3) . . . . ?
F7 C5 C6 F8 -0.3(2) . . . . ?
F7 C5 C6 C1 -179.8(2) . . . . ?
F8 C6 C1 C2 180.0(2) . . . . ?
F8 C6 C5 C4 178.9(2) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C1 C6 C5 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C2 C3 C4 C10 179.9(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C3 C4 C10 C9 123.1(2) . . . . ?
C3 C4 C10 C11 -57.5(2) . . . . ?
C4 C10 C9 C8 179.4(2) . . . . ?
C4 C10 C11 C12 -179.9(2) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C7 C12 C11 C10 0.2(3) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.4(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_I2F8bph_Me4pyrz
_database_code_depnum_ccdc_archive 'CCDC 2092660'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C12 F8 I2, C8 H12 N2'
_chemical_formula_sum            'C20 H12 F8 I2 N2'
_chemical_formula_weight         686.128
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   13.8570(6)
_cell_length_b                   13.7638(6)
_cell_length_c                   11.5041(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.737(2)
_cell_angle_gamma                90
_cell_volume                     2121.94(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.54
_exptl_absorpt_coefficient_mu    3.044
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1105 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.7578.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.148
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1293.736
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.071
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.9959
_diffrn_reflns_Laue_measured_fraction_max 0.9960
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13646
_diffrn_reflns_point_group_measured_fraction_full 0.9959
_diffrn_reflns_point_group_measured_fraction_max 0.9960
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         2.12
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9959
_diffrn_measured_fraction_theta_max 0.9960
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2100
_reflns_number_total             2251
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.4342
_refine_diff_density_min         -0.3605
_refine_diff_density_rms         0.0836
_refine_ls_d_res_high            0.7901
_refine_ls_d_res_low             9.6017
_refine_ls_goodness_of_fit_ref   1.0477
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    8
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0164
_refine_ls_restrained_S_all      1.0477
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0115P)²+5.0352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0389
_refine_ls_wR_factor_ref         0.0410
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
I1 I 0.422485(10) 0.732760(10) 0.375811(12) 0.01757(6) Uani 1.000000 .
F2 F 0.06519(9) 0.88881(8) 0.35696(11) 0.0191(3) Uani 1.000000 .
F3 F 0.05888(9) 0.58289(9) 0.16936(11) 0.0199(3) Uani 1.000000 .
F4 F 0.25773(9) 0.57971(9) 0.22798(12) 0.0204(3) Uani 1.000000 .
F1 F 0.26306(9) 0.88671(9) 0.41484(12) 0.0233(3) Uani 1.000000 .
N1 N 0.64632(14) 0.74693(12) 0.46838(16) 0.0154(4) Uani 1.000000 .
C1 C 0.26712(16) 0.73268(15) 0.3242(2) 0.0161(4) Uani 1.000000 .
C7 C 0.69534(16) 0.82841(15) 0.45218(18) 0.0149(4) Uani 1.000000 .
C3 C 0.11118(15) 0.81172(14) 0.32395(18) 0.0148(4) Uani 1.000000 .
C4 C 0.05505(16) 0.73485(14) 0.26409(19) 0.0139(4) Uani 1.000000 .
C5 C 0.10856(16) 0.65770(14) 0.23242(18) 0.0148(4) Uani 1.000000 .
C9 C 0.70026(16) 0.66899(15) 0.51613(18) 0.0149(4) Uani 1.000000 .
C2 C 0.21406(16) 0.81073(15) 0.35413(19) 0.0172(4) Uani 1.000000 .
C6 C 0.21126(16) 0.65659(14) 0.26139(18) 0.0151(4) Uani 1.000000 .
C10 C 0.64461(17) 0.57886(16) 0.5335(2) 0.0218(5) Uani 1.000000 .
C8 C 0.63441(17) 0.91540(16) 0.3995(2) 0.0220(5) Uani 1.000000 .
H10a H 0.6625(10) 0.5610(7) 0.6188(3) 0.0327(7) Uiso 1.000000 GR
H10b H 0.57266(17) 0.5911(4) 0.5069(14) 0.0327(7) Uiso 1.000000 GR
H10c H 0.6623(10) 0.5257(4) 0.4862(12) 0.0327(7) Uiso 1.000000 GR
H8a H 0.6449(10) 0.9295(7) 0.3201(7) 0.0330(7) Uiso 1.000000 GR
H8b H 0.5636(2) 0.9019(5) 0.3916(14) 0.0330(7) Uiso 1.000000 GR
H8c H 0.6550(9) 0.9715(3) 0.4524(8) 0.0330(7) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.083(2) . ?
F2 C3 1.341(2) . ?
F3 C5 1.344(2) . ?
F4 C6 1.345(2) . ?
F1 C2 1.342(2) . ?
N1 C7 1.348(3) . ?
N1 C9 1.343(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.391(3) . ?
C7 C9 1.400(3) 7_666 ?
C7 C8 1.501(3) . ?
C3 C4 1.388(3) . ?
C3 C2 1.379(3) . ?
C4 C4 1.477(4) 2 ?
C4 C5 1.396(3) . ?
C5 C6 1.377(3) . ?
C9 C10 1.501(3) . ?
C10 H10a 0.9800 . ?
C10 H10b 0.9800 . ?
C10 H10c 0.9800 . ?
C8 H8a 0.9800 . ?
C8 H8b 0.9800 . ?
C8 H8c 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C7 118.27(19) . . ?
C2 C1 I1 120.10(16) . . ?
C6 C1 I1 123.15(15) . . ?
C6 C1 C2 116.74(19) . . ?
C9 C7 N1 120.59(19) 7_666 . ?
C8 C7 N1 117.89(19) . . ?
C8 C7 C9 121.51(19) . 7_666 ?
C4 C3 F2 119.80(18) . . ?
C2 C3 F2 118.15(18) . . ?
C2 C3 C4 122.03(19) . . ?
C4 C4 C3 121.74(15) 2 . ?
C5 C4 C3 116.22(19) . . ?
C4 C5 F3 119.39(18) . . ?
C6 C5 F3 118.57(18) . . ?
C6 C5 C4 122.03(19) . . ?
C7 C9 N1 121.14(19) 7_666 . ?
C10 C9 N1 117.62(19) . . ?
C10 C9 C7 121.24(19) . 7_666 ?
C1 C2 F1 120.02(19) . . ?
C3 C2 F1 118.49(19) . . ?
C3 C2 C1 121.48(19) . . ?
C1 C6 F4 119.84(18) . . ?
C5 C6 F4 118.70(18) . . ?
C5 C6 C1 121.46(19) . . ?
H10a C10 C9 109.5 . . ?
H10b C10 C9 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C9 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H8a C8 C7 109.5 . . ?
H8b C8 C7 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 C7 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?


_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_Br2F4bz_44Me222bipy
_database_code_depnum_ccdc_archive 'CCDC 2093044'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'Br2 C6 F4, C12 H12 N2'
_chemical_formula_sum            'C18 H12 Br2 F4 N2'
_chemical_formula_weight         492.110
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   6.8796(6)
_cell_length_b                   7.4209(6)
_cell_length_c                   9.2086(8)
_cell_angle_alpha                82.848(3)
_cell_angle_beta                 82.965(3)
_cell_angle_gamma                75.554(3)
_cell_volume                     449.67(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8219
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.85
_exptl_absorpt_coefficient_mu    4.549
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0595 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.8644.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   .
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             239.726
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.9982
_diffrn_reflns_Laue_measured_fraction_max 0.9938
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10929
_diffrn_reflns_point_group_measured_fraction_full 0.9982
_diffrn_reflns_point_group_measured_fraction_max 0.9938
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.85
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9938
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1917
_reflns_number_total             2068
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.0561
_refine_diff_density_min         -0.4087
_refine_diff_density_rms         0.1124
_refine_ls_d_res_high            0.7672
_refine_ls_d_res_low             7.1519
_refine_ls_goodness_of_fit_ref   1.0540
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    10
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.0540
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+1.1283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0720
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
1.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c)
;
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_refinement_flags_posn
Br1 Br 0.75488(4) 0.41693(4) 0.58716(3) 0.01861(10) Uani 1.000000 .
F1 F 0.9691(3) 0.2967(2) 0.29190(18) 0.0213(3) Uani 1.000000 .
F2 F 1.1667(3) -0.0435(2) 0.22007(17) 0.0213(4) Uani 1.000000 .
N1 N 0.5226(4) 0.8072(3) 0.6435(3) 0.0186(5) Uani 1.000000 .
C1 C 0.8961(4) 0.1788(4) 0.5375(3) 0.0163(5) Uani 1.000000 .
C2 C 0.9832(4) 0.1515(4) 0.3960(3) 0.0166(5) Uani 1.000000 .
C3 C 1.0849(4) -0.0233(4) 0.3593(3) 0.0160(5) Uani 1.000000 .
C4 C 0.4645(5) 0.7781(4) 0.7868(3) 0.0224(6) Uani 1.000000 .
H4 H 0.4994(5) 0.6540(4) 0.8326(3) 0.0268(7) Uiso 1.000000 R
C5 C 0.3571(5) 0.9170(4) 0.8727(3) 0.0228(6) Uani 1.000000 .
H5 H 0.3206(5) 0.8877(4) 0.9742(3) 0.0274(7) Uiso 1.000000 R
C6 C 0.3030(4) 1.1005(4) 0.8085(3) 0.0193(5) Uani 1.000000 .
C7 C 0.3619(4) 1.1329(4) 0.6597(3) 0.0181(5) Uani 1.000000 .
H7 H 0.3295(4) 1.2561(4) 0.6118(3) 0.0217(6) Uiso 1.000000 R
C8 C 0.4693(4) 0.9838(4) 0.5803(3) 0.0150(5) Uani 1.000000 .
C9 C 0.1858(5) 1.2582(5) 0.8955(3) 0.0290(7) Uani 1.000000 .
H9a H 0.249(2) 1.3643(14) 0.874(2) 0.0435(10) Uiso 1.000000 GR
H9b H 0.0470(12) 1.297(2) 0.868(2) 0.0435(10) Uiso 1.000000 GR
H9c H 0.185(3) 1.2163(12) 1.0008(4) 0.0435(10) Uiso 1.000000 GR


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 1.874(3) . ?
F1 C2 1.343(3) . ?
F2 C3 1.346(3) . ?
N1 C4 1.338(4) . ?
N1 C8 1.347(4) . ?
C1 C2 1.383(4) . ?
C1 C3 1.391(4) 2_756 ?
C2 C3 1.373(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(4) . ?
C6 C7 1.389(4) . ?
C6 C9 1.506(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.403(4) . ?
C8 C8 1.493(5) 2_676 ?
C9 H9a 0.9800 . ?
C9 H9b 0.9800 . ?
C9 H9c 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
C8 N1 C4 116.9(2) . . ?
C2 C1 Br1 120.9(2) . . ?
C3 C1 Br1 121.4(2) 2_756 . ?
C3 C1 C2 117.7(2) 2_756 . ?
C1 C2 F1 120.2(2) . . ?
C3 C2 F1 118.9(2) . . ?
C3 C2 C1 121.0(3) . . ?
C1 C3 F2 119.7(2) 2_756 . ?
C2 C3 F2 118.9(2) . . ?
C2 C3 C1 121.4(2) . 2_756 ?
H4 C4 N1 117.83(16) . . ?
C5 C4 N1 124.3(3) . . ?
C5 C4 H4 117.83(17) . . ?
H5 C5 C4 120.43(17) . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.43(16) . . ?
C7 C6 C5 117.2(3) . . ?
C9 C6 C5 121.9(3) . . ?
C9 C6 C7 120.9(3) . . ?
H7 C7 C6 120.00(16) . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.00(16) . . ?
C7 C8 N1 122.4(2) . . ?
C8 C8 N1 117.1(3) 2_676 . ?
C8 C8 C7 120.6(3) 2_676 . ?
H9a C9 C6 109.5 . . ?
H9b C9 C6 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 C6 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 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
Br1 C1 C2 F1 0.6(2) . . . . ?
Br1 C1 C2 C3 -179.3(2) . . . . ?
Br1 C1 C3 F2 -0.9(2) . . 2_756 2_756 ?
Br1 C1 C3 C2 179.3(2) . . 2_756 2_756 ?
F1 C2 C1 C3 179.9(2) . . . 2_756 ?
F1 C2 C3 F2 -0.2(3) . . . . ?
F1 C2 C3 C1 -179.9(2) . . . 2_756 ?
F2 C3 C1 C2 -179.8(2) . . 2_756 2_756 ?
F2 C3 C2 C1 179.8(2) . . . . ?
N1 C4 C5 C6 0.3(4) . . . . ?
N1 C8 C7 C6 -1.3(3) . . . . ?
N1 C8 C8 N1 180.0(3) . . 2_676 2_676 ?
N1 C8 C8 C7 0.3(3) . . 2_676 2_676 ?
C1 C2 C3 C1 0.0(3) . . . 2_756 ?
C1 C3 C2 C1 0.0(3) 2_756 . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 C9 179.9(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C8 179.0(3) . . . 2_676 ?
C7 C8 C8 C7 -180.0(4) . . 2_676 2_676 ?


_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_I2F4bz_25Me2pyrz
_database_code_depnum_ccdc_archive 'CCDC 2092654'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C6 F4 I2, C6 H8 N2'
_chemical_formula_sum            'C12 H8 F4 I2 N2'
_chemical_formula_weight         510.013
_chemical_oxdiff_formula         (C6F4I2)(N2C6H8)
_chemical_oxdiff_usercomment     (2,5-Me2pyrz)(I2F4bz)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   5.7357(1)
_cell_length_b                   6.2412(1)
_cell_length_c                   10.6257(1)
_cell_angle_alpha                86.110(1)
_cell_angle_beta                 74.656(1)
_cell_angle_gamma                77.418(1)
_cell_volume                     357.986(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    18838
_cell_measurement_temperature    106(8)
_cell_measurement_theta_max      28.9960
_cell_measurement_theta_min      1.9720
_exptl_absorpt_coefficient_mu    4.427
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.390
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.366
_exptl_crystal_description       plate
_exptl_crystal_F_000             235.344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 0 0.1866
-2 -1 -2 0.1620
-1 0 -2 0.1255
1 0 2 0.1368
2 1 2 0.1500
1 1 0 0.1628
1 1 0 0.1529
-2 -1 -1 0.1605
2 1 1 0.1537
0 0 1 0.0720
0 0 -1 0.0926
-1 0 0 0.1451
1 0 0 0.1312
0 1 1 0.0897
0 -1 -1 0.0966
2 0 1 0.1314
-2 0 -1 0.1359
0 -2 0 0.1436
0 2 0 0.1160
-1 1 -1 0.1330

_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.165
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9997 -0.9997 -0.0004 0.0174 0.0785 0.1338
-1.9998 -0.9999 -1.5007 0.0055 0.0034 0.2571
-1.0001 -0.0002 -1.5003 -0.0119 -0.0751 0.1233
1.0001 0.0002 1.5003 0.0119 0.0751 -0.1233
1.9998 0.9999 1.5007 -0.0055 -0.0034 -0.2571
0.9997 0.9997 0.0004 -0.0174 -0.0785 -0.1338
0.9998 0.9998 -0.4996 0.0026 -0.1064 -0.1292
-1.9999 -0.9999 -1.0007 -0.0145 0.0312 0.2525
1.9999 0.9999 1.0007 0.0145 -0.0312 -0.2525
-0.0001 -0.0000 0.5000 -0.0201 0.0278 -0.0047
0.0001 0.0000 -0.5000 0.0201 -0.0278 0.0047
-1.0007 -0.0003 0.4998 -0.0922 0.0361 0.1046
1.0007 0.0003 -0.4998 0.0922 -0.0361 -0.1046
-0.0011 0.9994 1.0002 -0.1297 -0.0146 -0.0340
0.0011 -0.9994 -1.0002 0.1297 0.0146 0.0340
2.0009 0.0005 0.5005 0.1241 0.0112 -0.2232
-2.0009 -0.0005 -0.5005 -0.1241 -0.0112 0.2232
0.0016 -1.9990 0.4997 0.1590 0.1683 0.0445
-0.0016 1.9990 -0.4997 -0.1590 -0.1683 -0.0445
-1.0011 0.9993 -1.0001 -0.1215 -0.1176 0.0940

_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9746
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23215
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9746
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         1.99
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(8)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9746
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  89.00   0.50    0.34    --   14.30  15.00  30.00  210
  2  ω    -13.00  83.00   0.50    0.34    --   14.30  77.00-180.00  192
  3  ω    -16.00  89.00   0.50    0.34    --   14.30  15.00 -30.00  210
  4  ω     -3.00  82.00   0.50    0.34    --   14.30  45.00  30.00  170
  5  ω    -13.00  83.00   0.50    0.34    --   14.30  77.00  60.00  192
  6  ω     -8.00  82.00   0.50    0.34    --   14.30  61.00 150.00  180
  7  ω    -62.00  -4.00   0.50    0.34    --  -15.63 118.00 168.00  116
  8  ω    -66.00  -9.00   0.50    0.34    --  -15.63 125.00  90.00  114
  9  ω    -85.00 -26.00   0.50    0.34    --  -15.63 157.00 -36.00  118
 10  ω    -66.00  -9.00   0.50    0.34    --  -15.63 125.00-120.00  114
 11  ω    -66.00  -9.00   0.50    0.34    --  -15.63 125.00 -60.00  114
 12  ω    -64.00  -6.00   0.50    0.34    --  -15.63 121.00-162.86  116
 13  ω    -66.00  -9.00   0.50    0.34    --  -15.63 125.00 -30.00  114
 14  ω    -66.00  -9.00   0.50    0.34    --  -15.63 125.00   0.00  114
 15  ω    -66.00  -9.00   0.50    0.34    --  -15.63 125.00  30.00  114
 16  ω    -66.00  -9.00   0.50    0.34    --  -15.63 125.00 120.00  114
 17  ω    -64.00  -6.00   0.50    0.34    --  -15.63 121.00 178.47  116
 18  ω    -42.00  53.00   0.50    0.34    --  -15.63  77.00-180.00  190
 19  ω    -33.00  52.00   0.50    0.34    --  -15.63  45.00-180.00  170
 20  ω    -38.00  52.00   0.50    0.34    --  -15.63  61.00 -60.00  180
 21  ω    -33.00  52.00   0.50    0.34    --  -15.63  45.00 -60.00  170
 22  ω    -33.00  52.00   0.50    0.34    --  -15.63  45.00 150.00  170
 23  ω    -46.00  59.00   0.50    0.34    --  -15.63  15.00 150.00  210
 24  ω    -53.00  37.00   0.50    0.34    --   14.30 -61.00-120.00  180
 25  ω    -53.00  29.00   0.50    0.34    --   14.30 -45.00 -30.00  164
 26  ω    -54.00  14.00   0.50    0.34    --   14.30 -30.00   0.00  136
 27  ω    -60.00   3.00   0.50    0.34    --   14.30 -15.00-120.00  126
 28  ω    -54.00  14.00   0.50    0.34    --   14.30 -30.00-150.00  136
 29  ω    -60.00   3.00   0.50    0.34    --   14.30 -15.00 -60.00  126
 30  ω    -60.00   3.00   0.50    0.34    --   14.30 -15.00  30.00  126
 31  ω    -53.00  37.00   0.50    0.34    --   14.30 -61.00  30.00  180
 32  ω    -84.00  -3.00   0.50    0.34    --  -15.63 -30.00  30.00  162
 33  ω    -84.00  11.00   0.50    0.34    --  -15.63 -77.00 150.00  190
 34  ω    -83.00   7.00   0.50    0.34    --  -15.63 -61.00  90.00  180
 35  ω    -84.00  11.00   0.50    0.34    --  -15.63 -77.00  30.00  190
 36  ω    -84.00  -3.00   0.50    0.34    --  -15.63 -30.00 120.00  162
 37  ω    -83.00   7.00   0.50    0.34    --  -15.63 -61.00 -30.00  180
 38  ω    -83.00   7.00   0.50    0.34    --  -15.63 -61.00-120.00  180
 39  ω    -83.00   7.00   0.50    0.34    --  -15.63 -61.00-150.00  180
 40  ω    -38.00  17.00   0.50    0.34    --  -15.63 -94.00 -90.00  110
 41  ω    -38.00  17.00   0.50    0.34    --  -15.63 -94.00-120.00  110
 42  ω    -38.00  17.00   0.50    0.34    --  -15.63 -94.00-150.00  110
 43  ω    -38.00  17.00   0.50    0.34    --  -15.63 -94.00 -60.00  110
 44  ω    -38.00  17.00   0.50    0.34    --  -15.63 -94.00   0.00  110
 45  ω    -38.00  17.00   0.50    0.34    --  -15.63 -94.00  30.00  110
 46  ω    -38.00  17.00   0.50    0.34    --  -15.63 -94.00  90.00  110
 47  ω    -38.00  17.00   0.50    0.34    --  -15.63 -94.00 120.00  110
 48  ω      4.00  61.00   0.50    0.34    --   14.30-118.00  82.00  114
 49  ω      9.00  65.00   0.50    0.34    --   14.30-125.00 150.00  112
 50  ω      9.00  65.00   0.50    0.34    --   14.30-125.00   0.00  112
 51  ω     27.00  84.00   0.50    0.34    --   14.30-157.00 -71.00  114
 52  ω      9.00  65.00   0.50    0.34    --   14.30-125.00-150.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0720833000
_diffrn_orient_matrix_UB_12      -0.0894918000
_diffrn_orient_matrix_UB_13      -0.0401264000
_diffrn_orient_matrix_UB_21      -0.0082922000
_diffrn_orient_matrix_UB_22      -0.0702997000
_diffrn_orient_matrix_UB_23      0.0556216000
_diffrn_orient_matrix_UB_31      -0.1091844000
_diffrn_orient_matrix_UB_32      -0.0246965000
_diffrn_orient_matrix_UB_33      -0.0093898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1789
_reflns_number_total             1878
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.7094
_refine_diff_density_min         -0.7404
_refine_diff_density_rms         0.1926
_refine_ls_d_res_high            0.7293
_refine_ls_d_res_low             10.2463
_refine_ls_goodness_of_fit_ref   1.0986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    6
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1878
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0173
_refine_ls_restrained_S_all      1.0986
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0169P)²+0.2695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0373
_refine_ls_wR_factor_ref         0.0418
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
I1 I 0.56765(2) 0.27025(2) 0.237193(14) 0.01468(5) Uani 1.000000 .
F2 F 0.8695(3) 0.9202(2) -0.08191(14) 0.0187(3) Uani 1.000000 .
F1 F 0.5382(2) 0.7423(2) 0.09488(14) 0.0200(3) Uani 1.000000 .
N1 N 0.2050(4) 0.0797(3) 0.4288(2) 0.0167(4) Uani 1.000000 .
C3 C 0.9378(4) 0.7121(4) -0.0423(2) 0.0139(4) Uani 1.000000 .
C2 C 0.7665(4) 0.6196(4) 0.0488(2) 0.0137(4) Uani 1.000000 .
C1 C 0.8250(4) 0.4057(4) 0.0937(2) 0.0137(4) Uani 1.000000 .
C5 C 0.1217(4) -0.0739(4) 0.3816(2) 0.0169(5) Uani 1.000000 .
C4 C 0.0837(4) 0.1549(4) 0.5487(2) 0.0147(4) Uani 1.000000 .
C6 C 0.1770(5) 0.3223(4) 0.6046(3) 0.0220(5) Uani 1.000000 .
H5 H 0.2043(4) -0.1288(4) 0.2989(2) 0.0203(6) Uiso 1.000000 R
H6a H 0.317(2) 0.2514(6) 0.6362(17) 0.0330(8) Uiso 1.000000 GR
H6b H 0.225(3) 0.4279(18) 0.5382(5) 0.0330(8) Uiso 1.000000 GR
H6c H 0.0488(12) 0.395(2) 0.6753(12) 0.0330(8) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.097(2) . ?
F2 C3 1.345(2) . ?
F1 C2 1.347(3) . ?
N1 C5 1.338(3) . ?
N1 C4 1.340(3) . ?
C3 C2 1.379(3) . ?
C3 C1 1.384(3) 2_765 ?
C2 C1 1.388(3) . ?
C5 C4 1.392(3) 2_556 ?
C5 H5 0.9300 . ?
C4 C6 1.493(3) . ?
C6 H6a 0.9600 . ?
C6 H6b 0.9600 . ?
C6 H6c 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C5 117.4(2) . . ?
C2 C3 F2 118.7(2) . . ?
C1 C3 F2 120.1(2) 2_765 . ?
C1 C3 C2 121.3(2) 2_765 . ?
C3 C2 F1 118.5(2) . . ?
C1 C2 F1 119.9(2) . . ?
C1 C2 C3 121.6(2) . . ?
C3 C1 I1 121.50(16) 2_765 . ?
C2 C1 I1 121.32(17) . . ?
C2 C1 C3 117.2(2) . 2_765 ?
C4 C5 N1 122.7(2) 2_556 . ?
H5 C5 N1 118.64(14) . . ?
H5 C5 C4 118.64(14) . 2_556 ?
C5 C4 N1 119.8(2) 2_556 . ?
C6 C4 N1 118.4(2) . . ?
C6 C4 C5 121.8(2) . 2_556 ?
H6a C6 C4 109.5 . . ?
H6b C6 C4 109.5 . . ?
H6b C6 H6a 109.5 . . ?
H6c C6 C4 109.5 . . ?
H6c C6 H6a 109.5 . . ?
H6c C6 H6b 109.5 . . ?


_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 4.320
_oxdiff_exptl_absorpt_empirical_full_min 0.709
####################################################################### 
# 
# 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_Br2F8bph_quinox
_database_code_depnum_ccdc_archive 'CCDC 2092661'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'Br2 C12 F8, C8 H6 N2'
_chemical_formula_sum            'C20 H6 Br2 F8 N2'
_chemical_formula_weight         586.078
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.0424(4)
_cell_length_b                   7.0976(4)
_cell_length_c                   33.8513(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.497(2)
_cell_angle_gamma                90
_cell_volume                     1926.34(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7059
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.008
_cell_measurement_theta_min      2.541
_exptl_absorpt_coefficient_mu    4.295
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0787 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.7653.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1127.205
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.9971
_diffrn_reflns_Laue_measured_fraction_max 0.9937
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            15647
_diffrn_reflns_point_group_measured_fraction_full 0.9971
_diffrn_reflns_point_group_measured_fraction_max 0.9937
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         2.41
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9937
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              41
_reflns_limit_l_min              0
_reflns_number_gt                2964
_reflns_number_total             3778
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.6950
_refine_diff_density_min         -0.7941
_refine_diff_density_rms         0.1606
_refine_ls_d_res_high            0.8088
_refine_ls_d_res_low             8.4368
_refine_ls_goodness_of_fit_ref   1.0666
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3778
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.0666
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+2.5623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0928
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19)
;
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_refinement_flags_posn
Br1 Br 1.21853(5) -0.05980(6) 0.707780(11) 0.02207(12) Uani 1.000000 .
Br2 Br 0.62935(5) 0.55323(6) 0.437780(11) 0.02299(12) Uani 1.000000 .
F1 F 1.0130(3) 0.3051(3) 0.70113(6) 0.0250(5) Uani 1.000000 .
F2 F 0.8484(3) 0.4569(3) 0.63754(7) 0.0225(5) Uani 1.000000 .
F3 F 1.0642(3) -0.0121(3) 0.55658(6) 0.0208(5) Uani 1.000000 .
F4 F 1.2127(3) -0.1775(3) 0.62079(7) 0.0236(5) Uani 1.000000 .
F5 F 0.5866(3) 0.1593(3) 0.47429(7) 0.0273(5) Uani 1.000000 .
F6 F 0.7212(3) 0.0223(3) 0.54330(7) 0.0223(5) Uani 1.000000 .
F7 F 0.9831(3) 0.6069(3) 0.57159(7) 0.0220(5) Uani 1.000000 .
F8 F 0.8519(3) 0.7431(3) 0.50246(6) 0.0238(5) Uani 1.000000 .
C1 C 1.1147(5) 0.0574(5) 0.66257(11) 0.0189(8) Uani 1.000000 .
C2 C 1.0241(5) 0.2222(5) 0.66563(11) 0.0182(8) Uani 1.000000 .
C3 C 0.9418(5) 0.3019(5) 0.63258(11) 0.0172(8) Uani 1.000000 .
C4 C 0.9481(4) 0.2263(5) 0.59482(11) 0.0145(8) Uani 1.000000 .
C5 C 1.0447(5) 0.0644(5) 0.59228(11) 0.0176(8) Uani 1.000000 .
C6 C 1.1253(5) -0.0193(5) 0.62523(12) 0.0181(8) Uani 1.000000 .
C7 C 0.7148(5) 0.4552(6) 0.48680(11) 0.0184(8) Uani 1.000000 .
C8 C 0.6852(5) 0.2711(6) 0.49781(11) 0.0191(8) Uani 1.000000 .
C9 C 0.7561(5) 0.2010(5) 0.53345(11) 0.0174(8) Uani 1.000000 .
C10 C 0.8593(4) 0.3084(5) 0.55882(11) 0.0165(8) Uani 1.000000 .
C11 C 0.8835(5) 0.4950(5) 0.54790(12) 0.0176(8) Uani 1.000000 .
C12 C 0.8146(5) 0.5658(5) 0.51258(12) 0.0188(8) Uani 1.000000 .
N1 N 0.5408(4) 0.6848(5) 0.35835(10) 0.0209(7) Uani 1.000000 .
N2 N 0.3962(4) 0.7016(5) 0.27955(9) 0.0211(7) Uani 1.000000 .
C13 C 0.5588(5) 0.5496(6) 0.33252(12) 0.0223(9) Uani 1.000000 .
H13 H 0.6232(5) 0.4421(6) 0.34060(12) 0.0268(10) Uiso 1.000000 R
C14 C 0.4862(5) 0.5580(6) 0.29321(12) 0.0224(9) Uani 1.000000 .
H14 H 0.5031(5) 0.4554(6) 0.27593(12) 0.0269(10) Uiso 1.000000 R
C15 C 0.3754(5) 0.8457(6) 0.30564(11) 0.0193(8) Uani 1.000000 .
C16 C 0.2799(5) 1.0054(6) 0.29311(13) 0.0231(9) Uani 1.000000 .
H16 H 0.2298(5) 1.0123(6) 0.26679(13) 0.0277(11) Uiso 1.000000 R
C17 C 0.2602(5) 1.1502(6) 0.31914(13) 0.0261(9) Uani 1.000000 .
H17 H 0.1967(5) 1.2577(6) 0.31061(13) 0.0313(11) Uiso 1.000000 R
C18 C 0.3325(5) 1.1418(6) 0.35826(13) 0.0268(9) Uani 1.000000 .
H18 H 0.3166(5) 1.2429(6) 0.37597(13) 0.0322(11) Uiso 1.000000 R
C19 C 0.4257(5) 0.9891(6) 0.37102(13) 0.0241(9) Uani 1.000000 .
H19 H 0.4751(5) 0.9851(6) 0.39744(13) 0.0289(11) Uiso 1.000000 R
C20 C 0.4486(4) 0.8373(5) 0.34492(11) 0.0181(8) Uani 1.000000 .


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 1.879(4) . ?
Br2 C7 1.879(4) . ?
F1 C2 1.347(4) . ?
F2 C3 1.349(4) . ?
F3 C5 1.345(4) . ?
F4 C6 1.340(4) . ?
F5 C8 1.339(4) . ?
F6 C9 1.347(4) . ?
F7 C11 1.347(4) . ?
F8 C12 1.345(4) . ?
C1 C2 1.386(5) . ?
C1 C6 1.385(6) . ?
C2 C3 1.376(5) . ?
C3 C4 1.391(5) . ?
C4 C5 1.393(5) . ?
C4 C10 1.483(5) . ?
C5 C6 1.380(5) . ?
C7 C8 1.385(5) . ?
C7 C12 1.383(6) . ?
C8 C9 1.386(5) . ?
C9 C10 1.377(5) . ?
C10 C11 1.393(5) . ?
C11 C12 1.373(6) . ?
N1 C13 1.314(5) . ?
N1 C20 1.369(5) . ?
N2 C14 1.313(5) . ?
N2 C15 1.370(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.412(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.415(6) . ?
C15 C20 1.413(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.371(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.405(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.368(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.415(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 121.0(3) . . ?
C6 C1 Br1 121.0(3) . . ?
C6 C1 C2 118.0(4) . . ?
C1 C2 F1 120.5(3) . . ?
C3 C2 F1 119.0(3) . . ?
C3 C2 C1 120.5(4) . . ?
C2 C3 F2 118.1(3) . . ?
C4 C3 F2 119.3(3) . . ?
C4 C3 C2 122.6(3) . . ?
C5 C4 C3 115.8(3) . . ?
C10 C4 C3 123.6(3) . . ?
C10 C4 C5 120.6(3) . . ?
C4 C5 F3 119.5(3) . . ?
C6 C5 F3 118.2(3) . . ?
C6 C5 C4 122.3(4) . . ?
C1 C6 F4 120.1(3) . . ?
C5 C6 F4 119.2(4) . . ?
C5 C6 C1 120.7(3) . . ?
C8 C7 Br2 121.9(3) . . ?
C12 C7 Br2 120.1(3) . . ?
C12 C7 C8 118.0(4) . . ?
C7 C8 F5 120.4(3) . . ?
C9 C8 F5 119.3(3) . . ?
C9 C8 C7 120.4(4) . . ?
C8 C9 F6 118.3(3) . . ?
C10 C9 F6 119.6(3) . . ?
C10 C9 C8 122.1(4) . . ?
C9 C10 C4 121.5(3) . . ?
C11 C10 C4 121.6(3) . . ?
C11 C10 C9 116.8(3) . . ?
C10 C11 F7 119.4(3) . . ?
C12 C11 F7 118.9(3) . . ?
C12 C11 C10 121.6(4) . . ?
C7 C12 F8 120.0(3) . . ?
C11 C12 F8 118.8(3) . . ?
C11 C12 C7 121.1(4) . . ?
C20 N1 C13 116.2(3) . . ?
C15 N2 C14 116.4(3) . . ?
H13 C13 N1 118.8(2) . . ?
C14 C13 N1 122.5(4) . . ?
C14 C13 H13 118.8(2) . . ?
C13 C14 N2 122.7(4) . . ?
H14 C14 N2 118.6(2) . . ?
H14 C14 C13 118.6(2) . . ?
C16 C15 N2 119.7(4) . . ?
C20 C15 N2 120.8(4) . . ?
C20 C15 C16 119.5(4) . . ?
H16 C16 C15 120.2(2) . . ?
C17 C16 C15 119.7(4) . . ?
C17 C16 H16 120.2(3) . . ?
H17 C17 C16 119.5(3) . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.5(2) . . ?
H18 C18 C17 119.8(2) . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.8(3) . . ?
H19 C19 C18 120.0(3) . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19 120.0(2) . . ?
C15 C20 N1 121.4(3) . . ?
C19 C20 N1 119.2(4) . . ?
C19 C20 C15 119.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 F1 2.0(3) . . . . ?
Br1 C1 C2 C3 -176.8(3) . . . . ?
Br1 C1 C6 F4 -1.1(3) . . . . ?
Br1 C1 C6 C5 178.1(3) . . . . ?
Br2 C7 C8 F5 -3.4(3) . . . . ?
Br2 C7 C8 C9 177.2(3) . . . . ?
Br2 C7 C12 F8 -0.6(3) . . . . ?
Br2 C7 C12 C11 -177.6(3) . . . . ?
F1 C2 C1 C6 -178.5(3) . . . . ?
F1 C2 C3 F2 -2.2(4) . . . . ?
F1 C2 C3 C4 179.4(3) . . . . ?
F2 C3 C2 C1 176.6(3) . . . . ?
F2 C3 C4 C5 -178.8(3) . . . . ?
F2 C3 C4 C10 1.1(4) . . . . ?
F3 C5 C4 C3 -176.6(3) . . . . ?
F3 C5 C4 C10 3.4(4) . . . . ?
F3 C5 C6 F4 -3.2(4) . . . . ?
F3 C5 C6 C1 177.6(3) . . . . ?
F4 C6 C1 C2 179.4(3) . . . . ?
F4 C6 C5 C4 178.3(3) . . . . ?
F5 C8 C7 C12 178.6(3) . . . . ?
F5 C8 C9 F6 -0.7(4) . . . . ?
F5 C8 C9 C10 179.6(3) . . . . ?
F6 C9 C8 C7 178.7(3) . . . . ?
F6 C9 C10 C4 6.7(4) . . . . ?
F6 C9 C10 C11 -176.7(3) . . . . ?
F7 C11 C10 C4 -3.5(4) . . . . ?
F7 C11 C10 C9 179.9(3) . . . . ?
F7 C11 C12 F8 1.4(4) . . . . ?
F7 C11 C12 C7 178.4(3) . . . . ?
F8 C12 C7 C8 177.5(3) . . . . ?
F8 C12 C11 C10 -175.4(3) . . . . ?
C1 C2 C3 C4 -1.7(4) . . . . ?
C1 C6 C5 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C2 C3 C4 C10 179.4(3) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
C3 C4 C10 C9 -127.7(4) . . . . ?
C3 C4 C10 C11 55.9(4) . . . . ?
C4 C10 C9 C8 -173.6(3) . . . . ?
C4 C10 C11 C12 173.3(3) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C7 C12 C11 C10 1.6(4) . . . . ?
C8 C9 C10 C11 2.9(4) . . . . ?
C9 C10 C11 C12 -3.3(4) . . . . ?
N1 C13 C14 N2 0.4(5) . . . . ?
N1 C20 C15 N2 -0.8(4) . . . . ?
N1 C20 C15 C16 179.5(4) . . . . ?
N1 C20 C19 C18 -179.3(4) . . . . ?
N2 C15 C16 C17 -179.5(4) . . . . ?
N2 C15 C20 C19 179.5(4) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C15 C20 C19 C18 0.4(4) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C17 C18 C19 C20 -0.6(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_Br2F8bph_dpe
_database_code_depnum_ccdc_archive 'CCDC 2092668'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'Br2 C12 F8, C12 H10 N2'
_chemical_formula_sum            'C24 H10 Br2 F8 N2'
_chemical_formula_weight         638.155
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.3598(5)
_cell_length_b                   11.2484(8)
_cell_length_c                   13.8819(10)
_cell_angle_alpha                88.308(3)
_cell_angle_beta                 78.403(2)
_cell_angle_gamma                76.782(2)
_cell_volume                     1095.78(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14678
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.37
_exptl_absorpt_coefficient_mu    3.784
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0665 before and 0.0415 after correction.
The Ratio of minimum to maximum transmission is 0.8683.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             619.623
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.9927
_diffrn_reflns_Laue_measured_fraction_max 0.9914
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18362
_diffrn_reflns_point_group_measured_fraction_full 0.9927
_diffrn_reflns_point_group_measured_fraction_max 0.9914
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.37
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.9927
_diffrn_measured_fraction_theta_max 0.9914
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -8
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3741
_reflns_number_total             4267
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.5292
_refine_diff_density_min         -0.4839
_refine_diff_density_rms         0.1172
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             8.6003
_refine_ls_goodness_of_fit_ref   1.0766
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.0766
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0129P)²+2.1760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0605
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
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_refinement_flags_posn
Br1 Br 0.40765(4) 0.14571(3) 0.35389(2) 0.01642(8) Uani 1.000000 .
Br2 Br 0.93427(4) -0.58634(3) -0.19554(2) 0.01627(8) Uani 1.000000 .
F1 F 0.6254(2) 0.16585(15) 0.14474(13) 0.0214(4) Uani 1.000000 .
F2 F 0.7501(2) -0.00290(15) -0.00097(12) 0.0213(4) Uani 1.000000 .
F3 F 0.5267(2) -0.29488(15) 0.21432(12) 0.0197(4) Uani 1.000000 .
F4 F 0.3927(2) -0.12531(15) 0.35753(12) 0.0211(4) Uani 1.000000 .
F5 F 1.0279(2) -0.22362(15) -0.00056(13) 0.0193(4) Uani 1.000000 .
F6 F 1.1567(2) -0.41305(16) -0.12799(13) 0.0215(4) Uani 1.000000 .
F7 F 0.5287(2) -0.46399(15) -0.09896(13) 0.0192(4) Uani 1.000000 .
F8 F 0.4034(2) -0.28293(15) 0.03580(13) 0.0179(4) Uani 1.000000 .
C13 C 0.5021(4) 0.0254(3) 0.2538(2) 0.0140(6) Uani 1.000000 .
C14 C 0.5963(4) 0.0526(3) 0.1623(2) 0.0153(6) Uani 1.000000 .
C15 C 0.6636(4) -0.0346(3) 0.0881(2) 0.0151(6) Uani 1.000000 .
C16 C 0.6417(4) -0.1540(3) 0.1021(2) 0.0134(6) Uani 1.000000 .
C17 C 0.5496(4) -0.1805(3) 0.1949(2) 0.0148(6) Uani 1.000000 .
C18 C 0.4809(4) -0.0939(3) 0.2693(2) 0.0147(6) Uani 1.000000 .
C19 C 0.7126(4) -0.2492(2) 0.0235(2) 0.0130(6) Uani 1.000000 .
C20 C 0.9029(4) -0.2840(3) -0.0228(2) 0.0150(6) Uani 1.000000 .
C21 C 0.9692(4) -0.3807(3) -0.0889(2) 0.0145(6) Uani 1.000000 .
C22 C 0.8465(4) -0.4455(3) -0.1138(2) 0.0138(6) Uani 1.000000 .
C23 C 0.6544(4) -0.4077(3) -0.0730(2) 0.0146(6) Uani 1.000000 .
C24 C 0.5898(4) -0.3133(3) -0.0042(2) 0.0143(6) Uani 1.000000 .
N1 N 0.2898(3) 0.3583(2) 0.48068(19) 0.0165(5) Uani 1.000000 .
N2 N 0.0170(3) 1.1742(2) 0.71068(19) 0.0181(5) Uani 1.000000 .
C1 C 0.1805(4) 0.7397(3) 0.5554(2) 0.0163(6) Uani 1.000000 .
H1 H 0.1992(4) 0.7929(3) 0.5017(2) 0.0195(7) Uiso 1.000000 R
C2 C 0.1205(4) 0.7907(3) 0.6444(2) 0.0157(6) Uani 1.000000 .
H2 H 0.1010(4) 0.7383(3) 0.6986(2) 0.0189(7) Uiso 1.000000 R
C3 C 0.2208(4) 0.6082(3) 0.5319(2) 0.0135(6) Uani 1.000000 .
C4 C 0.2159(4) 0.5703(3) 0.4378(2) 0.0182(6) Uani 1.000000 .
H4 H 0.1900(4) 0.6290(3) 0.3888(2) 0.0218(8) Uiso 1.000000 R
C5 C 0.2488(4) 0.4471(3) 0.4161(2) 0.0181(6) Uani 1.000000 .
H5 H 0.2421(4) 0.4238(3) 0.3520(2) 0.0217(7) Uiso 1.000000 R
C6 C 0.2977(4) 0.3953(3) 0.5703(2) 0.0178(6) Uani 1.000000 .
H6 H 0.3278(4) 0.3344(3) 0.6171(2) 0.0214(7) Uiso 1.000000 R
C7 C 0.2647(4) 0.5165(3) 0.5991(2) 0.0160(6) Uani 1.000000 .
H7 H 0.2718(4) 0.5370(3) 0.6640(2) 0.0192(7) Uiso 1.000000 R
C8 C 0.0818(4) 0.9227(3) 0.6655(2) 0.0135(6) Uani 1.000000 .
C9 C 0.1389(4) 1.0055(3) 0.5948(2) 0.0152(6) Uani 1.000000 .
H9 H 0.2011(4) 0.9779(3) 0.5299(2) 0.0182(7) Uiso 1.000000 R
C10 C 0.1037(4) 1.1279(3) 0.6207(2) 0.0189(6) Uani 1.000000 .
H10 H 0.1434(4) 1.1825(3) 0.5717(2) 0.0227(8) Uiso 1.000000 R
C11 C -0.0382(4) 1.0953(3) 0.7781(2) 0.0170(6) Uani 1.000000 .
H11 H -0.1000(4) 1.1255(3) 0.8424(2) 0.0204(7) Uiso 1.000000 R
C12 C -0.0092(4) 0.9707(3) 0.7583(2) 0.0165(6) Uani 1.000000 .
H12 H -0.0519(4) 0.9185(3) 0.8086(2) 0.0198(7) Uiso 1.000000 R


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 C13 1.881(3) . ?
Br2 C22 1.886(3) . ?
F1 C14 1.347(3) . ?
F2 C15 1.350(3) . ?
F3 C17 1.348(3) . ?
F4 C18 1.344(3) . ?
F5 C20 1.348(3) . ?
F6 C21 1.346(3) . ?
F7 C23 1.342(3) . ?
F8 C24 1.341(3) . ?
C13 C14 1.381(4) . ?
C13 C18 1.391(4) . ?
C14 C15 1.379(4) . ?
C15 C16 1.392(4) . ?
C16 C17 1.388(4) . ?
C16 C19 1.481(4) . ?
C17 C18 1.376(4) . ?
C19 C20 1.390(4) . ?
C19 C24 1.392(4) . ?
C20 C21 1.378(4) . ?
C21 C22 1.381(4) . ?
C22 C23 1.385(4) . ?
C23 C24 1.383(4) . ?
N1 C5 1.346(4) . ?
N1 C6 1.340(4) . ?
N2 C10 1.344(4) . ?
N2 C11 1.339(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.326(4) . ?
C1 C3 1.473(4) . ?
C2 H2 0.9500 . ?
C2 C8 1.474(4) . ?
C3 C4 1.396(4) . ?
C3 C7 1.397(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.386(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(4) . ?
C8 C12 1.388(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.395(4) . ?
C12 H12 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
C14 C13 Br1 120.9(2) . . ?
C18 C13 Br1 121.4(2) . . ?
C18 C13 C14 117.7(3) . . ?
C13 C14 F1 119.9(3) . . ?
C15 C14 F1 118.8(3) . . ?
C15 C14 C13 121.3(3) . . ?
C14 C15 F2 119.2(3) . . ?
C16 C15 F2 119.1(3) . . ?
C16 C15 C14 121.7(3) . . ?
C17 C16 C15 116.4(3) . . ?
C19 C16 C15 122.7(3) . . ?
C19 C16 C17 120.9(3) . . ?
C16 C17 F3 119.6(3) . . ?
C18 C17 F3 118.1(3) . . ?
C18 C17 C16 122.3(3) . . ?
C13 C18 F4 119.9(3) . . ?
C17 C18 F4 119.4(3) . . ?
C17 C18 C13 120.6(3) . . ?
C20 C19 C16 123.0(2) . . ?
C24 C19 C16 120.6(3) . . ?
C24 C19 C20 116.3(3) . . ?
C19 C20 F5 119.1(3) . . ?
C21 C20 F5 118.8(2) . . ?
C21 C20 C19 122.1(3) . . ?
C20 C21 F6 119.1(2) . . ?
C22 C21 F6 120.0(3) . . ?
C22 C21 C20 120.9(3) . . ?
C21 C22 Br2 122.1(2) . . ?
C23 C22 Br2 119.8(2) . . ?
C23 C22 C21 118.0(3) . . ?
C22 C23 F7 120.1(3) . . ?
C24 C23 F7 119.2(2) . . ?
C24 C23 C22 120.7(3) . . ?
C19 C24 F8 119.7(3) . . ?
C23 C24 F8 118.5(2) . . ?
C23 C24 C19 121.8(3) . . ?
C6 N1 C5 116.0(3) . . ?
C11 N2 C10 116.7(3) . . ?
C2 C1 H1 116.94(18) . . ?
C3 C1 H1 116.94(16) . . ?
C3 C1 C2 126.1(3) . . ?
H2 C2 C1 117.59(18) . . ?
C8 C2 C1 124.8(3) . . ?
C8 C2 H2 117.59(16) . . ?
C4 C3 C1 119.6(3) . . ?
C7 C3 C1 123.7(3) . . ?
C7 C3 C4 116.7(3) . . ?
H4 C4 C3 120.11(17) . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.11(18) . . ?
C4 C5 N1 123.8(3) . . ?
H5 C5 N1 118.09(17) . . ?
H5 C5 C4 118.09(18) . . ?
H6 C6 N1 117.86(16) . . ?
C7 C6 N1 124.3(3) . . ?
C7 C6 H6 117.86(18) . . ?
C6 C7 C3 119.3(3) . . ?
H7 C7 C3 120.34(17) . . ?
H7 C7 C6 120.34(18) . . ?
C9 C8 C2 122.3(3) . . ?
C12 C8 C2 121.1(3) . . ?
C12 C8 C9 116.7(3) . . ?
H9 C9 C8 120.40(17) . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 120.40(18) . . ?
C9 C10 N2 124.1(3) . . ?
H10 C10 N2 117.94(17) . . ?
H10 C10 C9 117.94(18) . . ?
H11 C11 N2 118.49(17) . . ?
C12 C11 N2 123.0(3) . . ?
C12 C11 H11 118.49(18) . . ?
C11 C12 C8 120.3(3) . . ?
H12 C12 C8 119.84(17) . . ?
H12 C12 C11 119.84(18) . . ?

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 C13 C14 F1 1.6(2) . . . . ?
Br1 C13 C14 C15 -179.1(2) . . . . ?
Br1 C13 C18 F4 -0.5(2) . . . . ?
Br1 C13 C18 C17 179.5(2) . . . . ?
Br2 C22 C21 F6 4.2(2) . . . . ?
Br2 C22 C21 C20 -174.7(2) . . . . ?
Br2 C22 C23 F7 -6.5(2) . . . . ?
Br2 C22 C23 C24 172.6(2) . . . . ?
F1 C14 C13 C18 -178.0(2) . . . . ?
F1 C14 C15 F2 -2.5(3) . . . . ?
F1 C14 C15 C16 178.6(2) . . . . ?
F2 C15 C14 C13 178.2(2) . . . . ?
F2 C15 C16 C17 -179.2(2) . . . . ?
F2 C15 C16 C19 1.0(3) . . . . ?
F3 C17 C16 C15 -178.8(2) . . . . ?
F3 C17 C16 C19 1.0(3) . . . . ?
F3 C17 C18 F4 -0.6(3) . . . . ?
F3 C17 C18 C13 179.4(2) . . . . ?
F4 C18 C13 C14 179.0(3) . . . . ?
F4 C18 C17 C16 179.9(2) . . . . ?
F5 C20 C19 C16 -4.6(3) . . . . ?
F5 C20 C19 C24 178.6(2) . . . . ?
F5 C20 C21 F6 1.0(3) . . . . ?
F5 C20 C21 C22 179.9(2) . . . . ?
F6 C21 C20 C19 -177.2(2) . . . . ?
F6 C21 C22 C23 -179.0(2) . . . . ?
F7 C23 C22 C21 176.6(2) . . . . ?
F7 C23 C24 F8 1.4(3) . . . . ?
F7 C23 C24 C19 -178.1(2) . . . . ?
F8 C24 C19 C16 4.5(3) . . . . ?
F8 C24 C19 C20 -178.6(2) . . . . ?
F8 C24 C23 C22 -177.6(2) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C13 C18 C17 C16 -0.1(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C14 C15 C16 C19 179.9(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C15 C16 C19 C20 58.7(3) . . . . ?
C15 C16 C19 C24 -124.6(3) . . . . ?
C16 C19 C20 C21 173.6(3) . . . . ?
C16 C19 C24 C23 -175.9(3) . . . . ?
C19 C20 C21 C22 1.7(3) . . . . ?
C19 C24 C23 C22 2.8(3) . . . . ?
C20 C21 C22 C23 2.1(3) . . . . ?
C21 C22 C23 C24 -4.3(3) . . . . ?
N1 C5 C4 C3 -1.2(4) . . . . ?
N1 C6 C7 C3 -0.3(4) . . . . ?
N2 C10 C9 C8 0.1(3) . . . . ?
N2 C11 C12 C8 0.5(3) . . . . ?
C1 C2 C8 C9 -12.3(3) . . . . ?
C1 C2 C8 C12 169.6(3) . . . . ?
C1 C3 C4 C5 -178.3(3) . . . . ?
C1 C3 C7 C6 179.0(3) . . . . ?
C2 C8 C9 C10 -177.8(3) . . . . ?
C2 C8 C12 C11 177.5(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_I2F8bph_44bipy
_database_code_depnum_ccdc_archive 'CCDC 2092667'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C12 F8 I2, C10 H8 N2'
_chemical_formula_sum            'C22 H8 F8 I2 N2'
_chemical_formula_weight         706.118
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.9217(5)
_cell_length_b                   11.1526(9)
_cell_length_c                   12.8382(10)
_cell_angle_alpha                105.190(4)
_cell_angle_beta                 107.580(2)
_cell_angle_gamma                90.334(3)
_cell_volume                     1039.01(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.19
_exptl_absorpt_coefficient_mu    3.112
_exptl_absorpt_correction_T_max  0.745429
_exptl_absorpt_correction_T_min  0.648507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 61424 reflections, Rint = 0.0621
 (33545 with I > 3sig(I), Rint = 0.0505)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.257
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             662.879
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.041
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            61424
_diffrn_reflns_point_group_measured_fraction_full 0.9995
_diffrn_reflns_point_group_measured_fraction_max 0.9995
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.76
_diffrn_reflns_theta_min         2.19
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3740
_reflns_number_total             4423
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.6827
_refine_diff_density_min         -1.3693
_refine_diff_density_rms         0.3256
_refine_ls_d_res_high            0.7894
_refine_ls_d_res_low             9.3065
_refine_ls_goodness_of_fit_ref   1.0647
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.0647
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0000P)²+18.9701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0951
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C21(H21), C19(H19), C17(H17), C14(H14), C22(H22), C18(H18), C13(H13)
;
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_refinement_flags_posn
I1 I 0.63130(6) 0.38542(4) 0.26393(4) 0.01490(11) Uani 1.000000 .
I2 I 1.11438(5) 0.86079(4) 1.21492(4) 0.01547(11) Uani 1.000000 .
F7 F 1.0396(5) 0.8272(3) 0.7750(3) 0.0185(8) Uani 1.000000 .
F2 F 0.6663(5) 0.7572(3) 0.6397(3) 0.0174(8) Uani 1.000000 .
F5 F 0.8805(5) 0.6006(4) 1.0643(3) 0.0186(8) Uani 1.000000 .
F3 F 1.0004(5) 0.4182(3) 0.7008(3) 0.0183(8) Uani 1.000000 .
F4 F 0.8974(5) 0.3108(3) 0.4787(3) 0.0179(8) Uani 1.000000 .
F6 F 0.7721(5) 0.4874(3) 0.8430(3) 0.0185(8) Uani 1.000000 .
F8 F 1.1596(5) 0.9378(3) 0.9973(3) 0.0190(8) Uani 1.000000 .
F1 F 0.5437(5) 0.6418(4) 0.4175(3) 0.0195(8) Uani 1.000000 .
N1 N 0.5169(8) 0.2727(5) 0.0351(5) 0.0197(12) Uani 1.000000 .
N2 N 0.2221(7) -0.0262(5) -0.5547(5) 0.0186(12) Uani 1.000000 .
C7 C 1.0246(9) 0.7729(6) 1.0389(6) 0.0153(13) Uani 1.000000 .
C5 C 0.8911(8) 0.4760(6) 0.6326(5) 0.0130(12) Uani 1.000000 .
C8 C 0.9250(8) 0.6577(6) 0.9953(6) 0.0164(13) Uani 1.000000 .
C20 C 0.3292(9) 0.0918(6) -0.3210(6) 0.0162(13) Uani 1.000000 .
C15 C 0.3924(8) 0.1556(6) -0.1976(5) 0.0124(12) Uani 1.000000 .
C6 C 0.8334(8) 0.4195(6) 0.5156(6) 0.0135(13) Uani 1.000000 .
C2 C 0.6618(8) 0.5872(6) 0.4862(5) 0.0133(12) Uani 1.000000 .
C16 C 0.3718(9) 0.0949(6) -0.1190(6) 0.0174(13) Uani 1.000000 .
H16 H 0.3166(9) 0.0121(6) -0.1441(6) 0.0209(16) Uiso 1.000000 R
C11 C 0.9987(9) 0.7699(6) 0.8455(6) 0.0152(13) Uani 1.000000 .
C21 C 0.3838(9) -0.0256(6) -0.3645(6) 0.0189(14) Uani 1.000000 .
H21 H 0.4579(9) -0.0675(6) -0.3148(6) 0.0227(17) Uiso 1.000000 R
C9 C 0.8666(8) 0.5991(6) 0.8792(6) 0.0150(13) Uani 1.000000 .
C10 C 0.9019(8) 0.6543(6) 0.8025(6) 0.0143(13) Uani 1.000000 .
C4 C 0.8383(8) 0.5916(6) 0.6782(5) 0.0127(12) Uani 1.000000 .
C3 C 0.7229(9) 0.6462(6) 0.6020(6) 0.0175(14) Uani 1.000000 .
C12 C 1.0613(8) 0.8273(6) 0.9615(6) 0.0156(13) Uani 1.000000 .
C19 C 0.2191(9) 0.1474(6) -0.3983(6) 0.0181(14) Uani 1.000000 .
H19 H 0.1799(9) 0.2269(6) -0.3728(6) 0.0217(16) Uiso 1.000000 R
C17 C 0.4326(9) 0.1569(6) -0.0049(6) 0.0194(14) Uani 1.000000 .
H17 H 0.4144(9) 0.1163(6) 0.0478(6) 0.0233(17) Uiso 1.000000 R
C1 C 0.7179(8) 0.4736(6) 0.4408(6) 0.0156(13) Uani 1.000000 .
C14 C 0.4756(9) 0.2758(6) -0.1569(6) 0.0192(14) Uani 1.000000 .
H14 H 0.4908(9) 0.3205(6) -0.2076(6) 0.0231(17) Uiso 1.000000 R
C22 C 0.3278(9) -0.0788(7) -0.4805(6) 0.0212(15) Uani 1.000000 .
H22 H 0.3669(9) -0.1574(7) -0.5090(6) 0.0255(17) Uiso 1.000000 R
C18 C 0.1677(9) 0.0849(6) -0.5131(6) 0.0207(14) Uani 1.000000 .
H18 H 0.0899(9) 0.1225(6) -0.5651(6) 0.0248(17) Uiso 1.000000 R
C13 C 0.5370(9) 0.3300(7) -0.0389(6) 0.0208(14) Uani 1.000000 .
H13 H 0.5958(9) 0.4119(7) -0.0109(6) 0.0250(17) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.115(7) . ?
I2 C7 2.106(7) . ?
F7 C11 1.346(7) . ?
F2 C3 1.338(7) . ?
F5 C8 1.340(7) . ?
F3 C5 1.333(7) . ?
F4 C6 1.342(7) . ?
F6 C9 1.343(7) . ?
F8 C12 1.347(7) . ?
F1 C2 1.347(7) . ?
N1 C17 1.346(9) . ?
N1 C13 1.321(9) . ?
N2 C22 1.330(9) . ?
N2 C18 1.343(9) . ?
C7 C8 1.389(9) . ?
C7 C12 1.389(9) . ?
C5 C6 1.396(9) . ?
C5 C4 1.393(9) . ?
C8 C9 1.390(9) . ?
C20 C15 1.480(8) . ?
C20 C21 1.409(9) . ?
C20 C19 1.391(9) . ?
C15 C16 1.399(9) . ?
C15 C14 1.386(9) . ?
C6 C1 1.380(9) . ?
C2 C3 1.388(9) . ?
C2 C1 1.385(9) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(10) . ?
C11 C10 1.384(9) . ?
C11 C12 1.387(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.378(10) . ?
C9 C10 1.382(9) . ?
C10 C4 1.488(8) . ?
C4 C3 1.393(9) . ?
C19 H19 0.9500 . ?
C19 C18 1.386(10) . ?
C17 H17 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.402(10) . ?
C22 H22 0.9500 . ?
C18 H18 0.9500 . ?
C13 H13 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
C13 N1 C17 118.3(6) . . ?
C18 N2 C22 117.4(6) . . ?
C8 C7 I2 121.2(5) . . ?
C12 C7 I2 121.7(5) . . ?
C12 C7 C8 117.1(6) . . ?
C6 C5 F3 118.9(5) . . ?
C4 C5 F3 120.0(6) . . ?
C4 C5 C6 121.1(6) . . ?
C7 C8 F5 120.7(6) . . ?
C9 C8 F5 118.0(6) . . ?
C9 C8 C7 121.3(6) . . ?
C21 C20 C15 121.0(6) . . ?
C19 C20 C15 121.3(6) . . ?
C19 C20 C21 117.7(6) . . ?
C16 C15 C20 120.7(6) . . ?
C14 C15 C20 121.0(6) . . ?
C14 C15 C16 118.3(6) . . ?
C5 C6 F4 117.1(6) . . ?
C1 C6 F4 121.3(6) . . ?
C1 C6 C5 121.6(6) . . ?
C3 C2 F1 118.7(6) . . ?
C1 C2 F1 119.8(6) . . ?
C1 C2 C3 121.5(6) . . ?
H16 C16 C15 120.5(4) . . ?
C17 C16 C15 119.1(6) . . ?
C17 C16 H16 120.5(4) . . ?
C10 C11 F7 120.1(6) . . ?
C12 C11 F7 118.5(6) . . ?
C12 C11 C10 121.3(6) . . ?
H21 C21 C20 120.6(4) . . ?
C22 C21 C20 118.8(6) . . ?
C22 C21 H21 120.6(4) . . ?
C8 C9 F6 118.1(6) . . ?
C10 C9 F6 120.5(6) . . ?
C10 C9 C8 121.3(6) . . ?
C9 C10 C11 117.5(6) . . ?
C4 C10 C11 121.2(6) . . ?
C4 C10 C9 121.2(5) . . ?
C10 C4 C5 121.7(5) . . ?
C3 C4 C5 117.0(6) . . ?
C3 C4 C10 121.4(6) . . ?
C2 C3 F2 118.3(6) . . ?
C4 C3 F2 120.3(6) . . ?
C4 C3 C2 121.5(6) . . ?
C7 C12 F8 120.7(6) . . ?
C11 C12 F8 118.0(6) . . ?
C11 C12 C7 121.3(6) . . ?
H19 C19 C20 120.6(4) . . ?
C18 C19 C20 118.9(6) . . ?
C18 C19 H19 120.6(4) . . ?
C16 C17 N1 122.7(6) . . ?
H17 C17 N1 118.6(4) . . ?
H17 C17 C16 118.6(4) . . ?
C6 C1 I1 120.9(5) . . ?
C2 C1 I1 121.8(5) . . ?
C2 C1 C6 117.3(6) . . ?
H14 C14 C15 120.8(4) . . ?
C13 C14 C15 118.4(7) . . ?
C13 C14 H14 120.8(4) . . ?
C21 C22 N2 123.7(6) . . ?
H22 C22 N2 118.1(4) . . ?
H22 C22 C21 118.1(4) . . ?
C19 C18 N2 123.4(7) . . ?
H18 C18 N2 118.3(4) . . ?
H18 C18 C19 118.3(4) . . ?
C14 C13 N1 123.2(7) . . ?
H13 C13 N1 118.4(4) . . ?
H13 C13 C14 118.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C6 F4 1.4(6) . . . . ?
I1 C1 C6 C5 -179.6(5) . . . . ?
I1 C1 C2 F1 2.5(6) . . . . ?
I1 C1 C2 C3 -178.2(5) . . . . ?
I2 C7 C8 F5 1.3(5) . . . . ?
I2 C7 C8 C9 -179.5(5) . . . . ?
I2 C7 C12 F8 1.4(6) . . . . ?
I2 C7 C12 C11 -178.7(5) . . . . ?
F7 C11 C10 C9 178.9(6) . . . . ?
F7 C11 C10 C4 -1.1(7) . . . . ?
F7 C11 C12 F8 0.2(6) . . . . ?
F7 C11 C12 C7 -179.7(5) . . . . ?
F2 C3 C2 F1 -2.4(7) . . . . ?
F2 C3 C2 C1 178.4(6) . . . . ?
F2 C3 C4 C5 179.9(6) . . . . ?
F2 C3 C4 C10 0.0(7) . . . . ?
F5 C8 C7 C12 -178.4(6) . . . . ?
F5 C8 C9 F6 -1.3(6) . . . . ?
F5 C8 C9 C10 177.7(5) . . . . ?
F3 C5 C6 F4 -2.1(6) . . . . ?
F3 C5 C6 C1 178.9(5) . . . . ?
F3 C5 C4 C10 0.5(7) . . . . ?
F3 C5 C4 C3 -179.5(6) . . . . ?
F4 C6 C5 C4 177.0(5) . . . . ?
F4 C6 C1 C2 -178.6(6) . . . . ?
F6 C9 C8 C7 179.5(5) . . . . ?
F6 C9 C10 C11 179.4(6) . . . . ?
F6 C9 C10 C4 -0.6(7) . . . . ?
F8 C12 C7 C8 -178.9(6) . . . . ?
F8 C12 C11 C10 177.8(5) . . . . ?
F1 C2 C3 C4 176.9(5) . . . . ?
F1 C2 C1 C6 -177.4(6) . . . . ?
N1 C17 C16 C15 -2.2(8) . . . . ?
N1 C13 C14 C15 -1.0(8) . . . . ?
N2 C22 C21 C20 -0.9(8) . . . . ?
N2 C18 C19 C20 -1.7(8) . . . . ?
C7 C8 C9 C10 -1.5(8) . . . . ?
C7 C12 C11 C10 -2.0(7) . . . . ?
C5 C6 C1 C2 0.4(7) . . . . ?
C5 C4 C10 C11 119.4(6) . . . . ?
C5 C4 C10 C9 -60.6(7) . . . . ?
C5 C4 C3 C2 0.7(7) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
C8 C9 C10 C4 -179.6(6) . . . . ?
C20 C15 C16 C17 179.8(6) . . . . ?
C20 C15 C14 C13 -178.2(6) . . . . ?
C6 C1 C2 C3 1.8(8) . . . . ?
C2 C3 C4 C10 -179.2(6) . . . . ?
C11 C10 C4 C3 -60.7(7) . . . . ?
C9 C10 C4 C3 119.4(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_Br2F4bz_25Me2pyrz
_database_code_depnum_ccdc_archive 'CCDC 2092653'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'Br2 C6 F4, C6 H8 N2'
_chemical_formula_sum            'C12 H8 Br2 F4 N2'
_chemical_formula_weight         416.011
_chemical_oxdiff_formula         (Br2F4C6)(N2C6H8)
_chemical_oxdiff_usercomment     (I2F8bph)(Me3pyrz)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   4.8003(2)
_cell_length_b                   6.6036(2)
_cell_length_c                   10.9521(4)
_cell_angle_alpha                83.796(3)
_cell_angle_beta                 84.121(3)
_cell_angle_gamma                79.072(3)
_cell_volume                     337.69(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    16909
_cell_measurement_temperature    106(8)
_cell_measurement_theta_max      28.9760
_cell_measurement_theta_min      1.8630
_exptl_absorpt_coefficient_mu    6.037
_exptl_absorpt_correction_T_max  0.483
_exptl_absorpt_correction_T_min  0.040
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.046
_exptl_crystal_description       block
_exptl_crystal_F_000             199.711
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 0 0.2630
-1 -1 1 0.2116
-1 -1 2 0.1872
1 1 -2 0.2167
-2 -1 2 0.1772
2 1 -2 0.2023
-2 -1 1 0.1879
-1 0 2 0.1757
1 0 -2 0.1737
2 1 -1 0.2068
-2 -1 -1 0.2318
1 0 -1 0.1893
2 1 1 0.2725
2 0 -1 0.2100
-2 0 1 0.1855
0 -1 -2 0.2777
-1 -1 -2 0.3132
-1 0 0 0.2093
-2 1 2 0.1988
0 1 2 0.3262
1 0 0 0.2361
2 -1 -2 0.1786
2 -2 -1 0.2211
-1 0 -1 0.2344
-2 1 -1 0.2386
-1 1 0 0.2428
-1 2 1 0.2395
2 -1 1 0.2464
1 0 1 0.2752
1 -2 -1 0.2313
-2 2 -1 0.2516
2 -2 1 0.2370
0 -2 -1 0.2902
-1 1 -1 0.2562
0 2 1 0.3112
1 -2 2 0.2409
-1 0 -2 0.2380
-1 1 -2 0.2517
1 0 2 0.2889
0 -2 1 0.2357
0 2 -1 0.2289
0 1 -1 0.2026
0 -1 1 0.2092
0 -1 2 0.2028
0 1 -2 0.1919
0 0 1 0.2065
0 0 -1 0.2145

_exptl_crystal_size_max          0.688
_exptl_crystal_size_mid          0.475
_exptl_crystal_size_min          0.349
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -1.0000 -0.0000 0.0215 0.1078 0.1297
-1.0000 -1.0000 1.0000 0.0387 0.1602 0.0946
-1.0000 -1.0000 2.0000 0.0558 0.2127 0.0596
1.0000 1.0000 -2.0000 -0.0558 -0.2127 -0.0596
-2.0000 -1.0000 2.0000 -0.0223 0.3105 0.1441
2.0000 1.0000 -2.0000 0.0223 -0.3105 -0.1441
-2.0000 -1.0000 1.0000 -0.0394 0.2580 0.1791
-1.0000 0.0000 2.0000 -0.0438 0.2027 0.0145
1.0000 -0.0000 -2.0000 0.0438 -0.2027 -0.0145
2.0000 1.0000 -1.0000 0.0394 -0.2580 -0.1791
-2.0000 -1.0000 -1.0000 -0.0738 0.1531 0.2492
1.0000 -0.0000 -1.0000 0.0610 -0.1502 -0.0495
2.0000 1.0000 1.0000 0.0738 -0.1531 -0.2492
2.0000 -0.0000 -1.0000 0.1391 -0.2480 -0.1340
-2.0000 0.0000 1.0000 -0.1391 0.2480 0.1340
-0.0000 -1.0000 -2.0000 0.0653 -0.0950 0.1152
-1.0000 -1.0000 -2.0000 -0.0128 0.0028 0.1997
-1.0000 0.0000 0.0000 -0.0781 0.0978 0.0845
-2.0000 1.0000 2.0000 -0.2216 0.2905 0.0538
0.0000 1.0000 2.0000 -0.0653 0.0950 -0.1152
1.0000 -0.0000 -0.0000 0.0781 -0.0978 -0.0845
2.0000 -1.0000 -2.0000 0.2216 -0.2905 -0.0538
2.0000 -2.0000 -1.0000 0.3384 -0.2281 -0.0437
-1.0000 -0.0000 -1.0000 -0.0953 0.0453 0.1195
-2.0000 1.0000 -1.0000 -0.2731 0.1331 0.1589
-1.0000 1.0000 0.0000 -0.1778 0.0878 0.0394
-1.0000 2.0000 1.0000 -0.2602 0.1303 -0.0408
2.0000 -1.0000 1.0000 0.2731 -0.1331 -0.1589
1.0000 0.0000 1.0000 0.0953 -0.0453 -0.1195
1.0000 -2.0000 -1.0000 0.2602 -0.1303 0.0408
-2.0000 2.0000 -1.0000 -0.3727 0.1232 0.1138
2.0000 -2.0000 1.0000 0.3727 -0.1232 -0.1138
0.0000 -2.0000 -1.0000 0.1821 -0.0325 0.1253
-1.0000 1.0000 -1.0000 -0.1949 0.0354 0.0744
-0.0000 2.0000 1.0000 -0.1821 0.0325 -0.1253
1.0000 -2.0000 2.0000 0.3117 0.0271 -0.0643
-1.0000 -0.0000 -2.0000 -0.1125 -0.0071 0.1546
-1.0000 1.0000 -2.0000 -0.2121 -0.0171 0.1094
1.0000 0.0000 2.0000 0.1125 0.0071 -0.1546
0.0000 -2.0000 1.0000 0.2165 0.0724 0.0553
-0.0000 2.0000 -1.0000 -0.2165 -0.0724 -0.0553
-0.0000 1.0000 -1.0000 -0.1168 -0.0624 -0.0101
0.0000 -1.0000 1.0000 0.1168 0.0624 0.0101
0.0000 -1.0000 2.0000 0.1340 0.1149 -0.0249
-0.0000 1.0000 -2.0000 -0.1340 -0.1149 0.0249
0.0000 0.0000 1.0000 0.0172 0.0525 -0.0350
-0.0000 -0.0000 -1.0000 -0.0172 -0.0525 0.0350

_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9699
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23811
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9699
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         1.88
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(8)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9699
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  83.00   0.50    0.31    --   14.30  77.00 -90.00  192
  2  ω    -13.00  83.00   0.50    0.31    --   14.30  77.00 -60.00  192
  3  ω    -13.00  84.00   0.50    0.31    --   14.30  78.00 134.00  194
  4  ω     -8.00  82.00   0.50    0.31    --   14.30  61.00 150.00  180
  5  ω     -3.00  82.00   0.50    0.31    --   14.30  45.00 120.00  170
  6  ω     -3.00  82.00   0.50    0.31    --   14.30  45.00  90.00  170
  7  ω    -16.00  89.00   0.50    0.31    --   14.30  15.00 150.00  210
  8  ω    -16.00  89.00   0.50    0.31    --   14.30  15.00  60.00  210
  9  ω    -62.00   6.00   0.50    0.31    --   14.30   0.00 -30.00  136
 10  ω    -16.00  89.00   0.50    0.31    --   14.30  15.00 -60.00  210
 11  ω    -62.00  90.00   0.50    0.31    --   14.30   0.00 -90.00  304
 12  ω    -62.00  90.00   0.50    0.31    --   14.30   0.00 -60.00  304
 13  ω    -62.00  90.00   0.50    0.31    --   14.30   0.00-120.00  304
 14  ω    -62.00  90.00   0.50    0.31    --   14.30   0.00-180.00  304
 15  ω    -62.00  90.00   0.50    0.31    --   14.30   0.00-150.00  304
 16  ω    -66.00  -9.00   0.50    0.31    --  -15.63 125.00 -60.00  114
 17  ω    -66.00  -9.00   0.50    0.31    --  -15.63 125.00 -90.00  114
 18  ω    -66.00  -9.00   0.50    0.31    --  -15.63 125.00-150.00  114
 19  ω    -66.00  -9.00   0.50    0.31    --  -15.63 125.00 -30.00  114
 20  ω    -66.00  -9.00   0.50    0.31    --  -15.63 125.00  60.00  114
 21  ω    -66.00  -9.00   0.50    0.31    --  -15.63 125.00 150.00  114
 22  ω    -43.00  54.00   0.50    0.31    --  -15.63  78.00 134.00  194
 23  ω    -42.00  53.00   0.50    0.31    --  -15.63  77.00  60.00  190
 24  ω    -28.00  53.00   0.50    0.31    --  -15.63  30.00 -60.00  162
 25  ω    -28.00  53.00   0.50    0.31    --  -15.63  30.00 -90.00  162
 26  ω    -60.00   3.00   0.50    0.31    --   14.30 -15.00   0.00  126
 27  ω    -54.00  14.00   0.50    0.31    --   14.30 -30.00 -60.00  136
 28  ω    -53.00  37.00   0.50    0.31    --   14.30 -61.00 -30.00  180
 29  ω    -55.00  42.00   0.50    0.31    --   14.30 -78.00   8.00  194
 30  ω    -54.00  14.00   0.50    0.31    --   14.30 -30.00  60.00  136
 31  ω    -60.00   3.00   0.50    0.31    --   14.30 -15.00 150.00  126
 32  ω    -84.00  -3.00   0.50    0.31    --  -15.63 -30.00 150.00  162
 33  ω    -82.00   2.00   0.50    0.31    --  -15.63 -45.00 150.00  168
 34  ω    -84.00  12.00   0.50    0.31    --  -15.63 -78.00   8.00  192
 35  ω    -82.00   2.00   0.50    0.31    --  -15.63 -45.00 -90.00  168
 36  ω      9.00  65.00   0.50    0.31    --   14.30-125.00 -30.00  112
 37  ω      9.00  65.00   0.50    0.31    --   14.30-125.00-150.00  112
 38  ω      9.00  65.00   0.50    0.31    --   14.30-125.00 -90.00  112
 39  ω      9.00  65.00   0.50    0.31    --   14.30-125.00 -60.00  112
 40  ω      9.00  65.00   0.50    0.31    --   14.30-125.00 120.00  112
 41  ω    -38.00  47.00   0.50    0.31    --   14.30 -94.00 150.00  170
 42  ω    -38.00  17.00   0.50    0.31    --  -15.63 -94.00 -30.00  110
 43  ω    -38.00  17.00   0.50    0.31    --  -15.63 -94.00   0.00  110
 44  ω    -38.00  17.00   0.50    0.31    --  -15.63 -94.00 120.00  110
 45  ω    -38.00  17.00   0.50    0.31    --  -15.63 -94.00 -60.00  110
 46  ω    -38.00  17.00   0.50    0.31    --  -15.63 -94.00-180.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0781268000
_diffrn_orient_matrix_UB_12      -0.0996436000
_diffrn_orient_matrix_UB_13      0.0171648000
_diffrn_orient_matrix_UB_21      -0.0977868000
_diffrn_orient_matrix_UB_22      -0.0099683000
_diffrn_orient_matrix_UB_23      0.0524630000
_diffrn_orient_matrix_UB_31      -0.0845109000
_diffrn_orient_matrix_UB_32      -0.0451484000
_diffrn_orient_matrix_UB_33      -0.0350296000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1586
_reflns_number_total             1770
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.5187
_refine_diff_density_min         -0.7372
_refine_diff_density_rms         0.1336
_refine_ls_d_res_high            0.7292
_refine_ls_d_res_low             10.8495
_refine_ls_goodness_of_fit_ref   1.0432
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    6
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1770
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.0432
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+0.0849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0626
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C5(H5)
1.b Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c)
;
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_refinement_flags_posn
Br1 Br 0.74002(5) 0.18180(3) 0.72831(2) 0.02074(9) Uani 1.000000 .
F1 F 0.2805(3) 0.39108(19) 0.55795(13) 0.0238(3) Uani 1.000000 .
F2 F 0.0818(3) 0.2408(2) 0.37285(13) 0.0269(3) Uani 1.000000 .
C1 C 0.6035(5) 0.0792(4) 0.5972(2) 0.0200(5) Uani 1.000000 .
C2 C 0.3914(5) 0.1973(3) 0.5300(2) 0.0190(5) Uani 1.000000 .
C3 C 0.2896(5) 0.1206(3) 0.4353(2) 0.0190(5) Uani 1.000000 .
N1 N 0.9375(4) 0.3597(3) 0.92573(19) 0.0206(4) Uani 1.000000 .
C4 C 0.8403(5) 0.3569(3) 1.0443(2) 0.0198(5) Uani 1.000000 .
C5 C 1.0952(5) 0.5014(4) 0.8824(2) 0.0214(5) Uani 1.000000 .
H5 H 1.1650(5) 0.5060(4) 0.8000(2) 0.0257(6) Uiso 1.000000 R
C6 C 0.6618(6) 0.1987(4) 1.0949(3) 0.0280(6) Uani 1.000000 .
H6a H 0.512(3) 0.203(2) 1.0423(10) 0.0420(9) Uiso 1.000000 GR
H6b H 0.7786(10) 0.0633(5) 1.0986(17) 0.0420(9) Uiso 1.000000 GR
H6c H 0.580(3) 0.2284(18) 1.1762(7) 0.0420(9) Uiso 1.000000 GR


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 1.877(2) . ?
F1 C2 1.345(2) . ?
F2 C3 1.347(3) . ?
C1 C2 1.384(3) . ?
C1 C3 1.392(3) 2_656 ?
C2 C3 1.372(3) . ?
N1 C4 1.334(3) . ?
N1 C5 1.332(3) . ?
C4 C5 1.392(3) 2_767 ?
C4 C6 1.500(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 121.61(18) . . ?
C3 C1 Br1 121.00(19) 2_656 . ?
C3 C1 C2 117.4(2) 2_656 . ?
C1 C2 F1 119.7(2) . . ?
C3 C2 F1 118.9(2) . . ?
C3 C2 C1 121.4(2) . . ?
C1 C3 F2 119.4(2) 2_656 . ?
C2 C3 F2 119.3(2) . . ?
C2 C3 C1 121.2(2) . 2_656 ?
C5 N1 C4 117.4(2) . . ?
C5 C4 N1 120.0(2) 2_767 . ?
C6 C4 N1 118.2(2) . . ?
C6 C4 C5 121.7(2) . 2_767 ?
C4 C5 N1 122.6(2) 2_767 . ?

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 C2 F1 0.5(2) . . . . ?
Br1 C1 C2 C3 -179.09(18) . . . . ?
Br1 C1 C3 F2 -1.0(2) . . 2_656 2_656 ?
Br1 C1 C3 C2 179.10(18) . . 2_656 2_656 ?
F1 C2 C1 C3 179.8(2) . . . 2_656 ?
F1 C2 C3 F2 0.0(2) . . . . ?
F1 C2 C3 C1 -179.8(2) . . . 2_656 ?
F2 C3 C1 C2 -179.7(2) . . 2_656 2_656 ?
F2 C3 C2 C1 179.6(2) . . . . ?
C1 C2 C3 C1 -0.2(2) . . . 2_656 ?
C1 C3 C2 C1 -0.2(2) 2_656 . . . ?
N1 C4 C5 N1 0.0(2) . . 2_767 2_767 ?
N1 C5 C4 N1 -0.0(2) . . 2_767 2_767 ?
N1 C5 C4 C6 179.9(2) . . 2_767 2_767 ?


_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.771
####################################################################### 
# 
# 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_Br2F8bph_25Me2pyrz
_database_code_depnum_ccdc_archive 'CCDC 2092655'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br2 C12 F8, C6 H8 N2'
_chemical_formula_sum            'C18 H8 Br2 F8 N2'
_chemical_formula_weight         564.08
_chemical_absolute_configuration .
_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'

_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.9213(6)
_cell_length_b                   12.3927(6)
_cell_length_c                   11.7294(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1878.23(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6255
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.594
_shelx_estimated_absorpt_T_min   0.443
_exptl_absorpt_coefficient_mu    4.401
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0728 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.8191.
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    1.995
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.132
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14714
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.277
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3225
_reflns_number_total             3824
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1352 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0216
_refine_ls_restrained_S_all      1.007
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0447
_refine_ls_wR_factor_ref         0.0473
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15)
1.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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 0.25034(3) 0.23080(3) 0.54587(3) 0.01943(10) Uani 1 1 d . . . . .
Br2 Br 0.24525(3) 1.06999(3) 0.27298(3) 0.01758(10) Uani 1 1 d . . . . .
F1 F 0.41173(17) 0.3544(2) 0.4074(2) 0.0212(5) Uani 1 1 d . . . . .
F2 F 0.41078(17) 0.55937(19) 0.3384(2) 0.0194(6) Uani 1 1 d . . . . .
F3 F 0.09299(17) 0.61493(19) 0.5273(2) 0.0171(5) Uani 1 1 d . . . . .
F4 F 0.0897(2) 0.4083(2) 0.5898(2) 0.0214(6) Uani 1 1 d . . . . .
F5 F 0.08792(18) 0.8913(2) 0.2321(2) 0.0199(6) Uani 1 1 d . . . . .
F6 F 0.08845(17) 0.6875(2) 0.30325(19) 0.0180(6) Uani 1 1 d . . . . .
F7 F 0.41537(18) 0.74123(19) 0.4739(2) 0.0184(6) Uani 1 1 d . . . . .
F8 F 0.41455(19) 0.9465(2) 0.4020(2) 0.0210(6) Uani 1 1 d . . . . .
C1 C 0.2508(3) 0.3755(3) 0.4994(3) 0.0163(8) Uani 1 1 d . . . . .
C2 C 0.3314(4) 0.4171(4) 0.4373(4) 0.0168(10) Uani 1 1 d . . . . .
C3 C 0.3321(3) 0.5235(3) 0.4023(3) 0.0136(9) Uani 1 1 d . . . . .
C4 C 0.2514(3) 0.5936(3) 0.4299(4) 0.0136(9) Uani 1 1 d . . . . .
C5 C 0.1711(3) 0.5511(4) 0.4933(3) 0.0145(9) Uani 1 1 d . . . . .
C6 C 0.1693(3) 0.4448(3) 0.5271(3) 0.0159(9) Uani 1 1 d . . . . .
C7 C 0.2499(3) 0.9246(3) 0.3183(3) 0.0145(8) Uani 1 1 d . . . . .
C8 C 0.1688(3) 0.8565(4) 0.2945(3) 0.0148(9) Uani 1 1 d . . . . .
C9 C 0.1682(3) 0.7503(4) 0.3308(3) 0.0145(9) Uani 1 1 d . . . . .
C10 C 0.2513(3) 0.7082(4) 0.3921(4) 0.0140(9) Uani 1 1 d . . . . .
C11 C 0.3333(3) 0.7777(4) 0.4138(4) 0.0149(9) Uani 1 1 d . . . . .
C12 C 0.3335(3) 0.8831(4) 0.3779(4) 0.0140(9) Uani 1 1 d . . . . .
N1 N 0.2569(3) 0.0085(3) 0.6219(3) 0.0176(8) Uani 1 1 d . . . . .
N2 N 0.2633(3) -0.2044(3) 0.6994(3) 0.0207(8) Uani 1 1 d . . . . .
C13 C 0.3412(3) -0.0338(4) 0.6702(4) 0.0195(10) Uani 1 1 d . . . . .
H13 H 0.401040 0.010224 0.677461 0.023 Uiso 1 1 calc R U . . .
C14 C 0.3456(3) -0.1396(4) 0.7103(3) 0.0175(10) Uani 1 1 d . . . . .
C15 C 0.1788(3) -0.1614(4) 0.6495(4) 0.0198(10) Uani 1 1 d . . . . .
H15 H 0.119705 -0.206001 0.639584 0.024 Uiso 1 1 calc R U . . .
C16 C 0.1739(3) -0.0560(4) 0.6123(4) 0.0166(9) Uani 1 1 d . . . . .
C17 C 0.4401(3) -0.1851(4) 0.7677(4) 0.0285(10) Uani 1 1 d . . . . .
H17A H 0.426368 -0.194217 0.849291 0.043 Uiso 1 1 calc R U . . .
H17B H 0.498404 -0.135558 0.757221 0.043 Uiso 1 1 calc R U . . .
H17C H 0.457032 -0.255257 0.733901 0.043 Uiso 1 1 calc R U . . .
C18 C 0.0775(3) -0.0104(4) 0.5605(4) 0.0260(11) Uani 1 1 d . . . . .
H18A H 0.056091 0.053783 0.603376 0.039 Uiso 1 1 calc R U . . .
H18B H 0.022260 -0.064517 0.563329 0.039 Uiso 1 1 calc R U . . .
H18C H 0.090916 0.009568 0.481061 0.039 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 1.874(4) . ?
Br2 C7 1.880(4) . ?
F1 C2 1.343(5) . ?
F2 C3 1.339(5) . ?
F3 C5 1.343(5) . ?
F4 C6 1.342(5) . ?
F5 C8 1.347(4) . ?
F6 C9 1.331(5) . ?
F7 C11 1.351(5) . ?
F8 C12 1.340(5) . ?
C1 C2 1.372(6) . ?
C1 C6 1.398(6) . ?
C2 C3 1.381(6) . ?
C3 C4 1.396(6) . ?
C4 C5 1.382(6) . ?
C4 C10 1.487(5) . ?
C5 C6 1.376(6) . ?
C7 C8 1.374(6) . ?
C7 C12 1.385(6) . ?
C8 C9 1.384(6) . ?
C9 C10 1.394(6) . ?
C10 C11 1.389(6) . ?
C11 C12 1.372(6) . ?
N1 C13 1.335(5) . ?
N1 C16 1.342(5) . ?
N2 C14 1.338(6) . ?
N2 C15 1.348(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(6) . ?
C14 C17 1.504(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(6) . ?
C16 C18 1.497(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C2 C1 Br1 121.1(3) . . ?
C2 C1 C6 117.7(4) . . ?
C6 C1 Br1 121.2(3) . . ?
F1 C2 C1 120.5(4) . . ?
F1 C2 C3 118.0(4) . . ?
C1 C2 C3 121.5(4) . . ?
F2 C3 C2 119.2(4) . . ?
F2 C3 C4 119.4(4) . . ?
C2 C3 C4 121.4(4) . . ?
C3 C4 C10 121.7(4) . . ?
C5 C4 C3 116.6(4) . . ?
C5 C4 C10 121.6(4) . . ?
F3 C5 C4 119.9(4) . . ?
F3 C5 C6 117.8(4) . . ?
C6 C5 C4 122.2(4) . . ?
F4 C6 C1 119.9(4) . . ?
F4 C6 C5 119.5(4) . . ?
C5 C6 C1 120.6(4) . . ?
C8 C7 Br2 120.4(3) . . ?
C8 C7 C12 118.0(4) . . ?
C12 C7 Br2 121.6(3) . . ?
F5 C8 C7 120.4(4) . . ?
F5 C8 C9 117.9(4) . . ?
C7 C8 C9 121.7(4) . . ?
F6 C9 C8 119.0(4) . . ?
F6 C9 C10 120.2(4) . . ?
C8 C9 C10 120.7(4) . . ?
C9 C10 C4 120.8(4) . . ?
C11 C10 C4 122.4(4) . . ?
C11 C10 C9 116.8(4) . . ?
F7 C11 C10 119.1(4) . . ?
F7 C11 C12 118.5(4) . . ?
C12 C11 C10 122.3(4) . . ?
F8 C12 C7 119.9(4) . . ?
F8 C12 C11 119.6(4) . . ?
C11 C12 C7 120.5(4) . . ?
C13 N1 C16 117.0(4) . . ?
C14 N2 C15 116.6(4) . . ?
N1 C13 H13 118.5 . . ?
N1 C13 C14 123.0(4) . . ?
C14 C13 H13 118.5 . . ?
N2 C14 C13 120.0(4) . . ?
N2 C14 C17 117.6(4) . . ?
C13 C14 C17 122.4(4) . . ?
N2 C15 H15 118.4 . . ?
N2 C15 C16 123.3(4) . . ?
C16 C15 H15 118.4 . . ?
N1 C16 C15 120.1(4) . . ?
N1 C16 C18 118.3(4) . . ?
C15 C16 C18 121.7(4) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
Br1 C1 C2 F1 0.5(6) . . . . ?
Br1 C1 C2 C3 179.7(3) . . . . ?
Br1 C1 C6 F4 1.3(5) . . . . ?
Br1 C1 C6 C5 179.4(3) . . . . ?
Br2 C7 C8 F5 4.2(5) . . . . ?
Br2 C7 C8 C9 -177.3(3) . . . . ?
Br2 C7 C12 F8 -1.6(5) . . . . ?
Br2 C7 C12 C11 177.5(3) . . . . ?
F1 C2 C3 F2 1.4(6) . . . . ?
F1 C2 C3 C4 180.0(4) . . . . ?
F2 C3 C4 C5 178.3(4) . . . . ?
F2 C3 C4 C10 -1.2(6) . . . . ?
F3 C5 C6 F4 1.4(6) . . . . ?
F3 C5 C6 C1 -176.8(3) . . . . ?
F5 C8 C9 F6 -0.1(6) . . . . ?
F5 C8 C9 C10 177.7(3) . . . . ?
F6 C9 C10 C4 -1.4(5) . . . . ?
F6 C9 C10 C11 177.6(4) . . . . ?
F7 C11 C12 F8 0.6(6) . . . . ?
F7 C11 C12 C7 -178.5(4) . . . . ?
C1 C2 C3 F2 -177.7(4) . . . . ?
C1 C2 C3 C4 0.8(7) . . . . ?
C2 C1 C6 F4 -178.6(4) . . . . ?
C2 C1 C6 C5 -0.5(6) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C2 C3 C4 C10 -179.7(4) . . . . ?
C3 C4 C5 F3 177.1(3) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C3 C4 C10 C9 125.1(5) . . . . ?
C3 C4 C10 C11 -53.9(5) . . . . ?
C4 C5 C6 F4 179.2(4) . . . . ?
C4 C5 C6 C1 1.0(7) . . . . ?
C4 C10 C11 F7 -1.7(6) . . . . ?
C4 C10 C11 C12 179.4(4) . . . . ?
C5 C4 C10 C9 -54.3(5) . . . . ?
C5 C4 C10 C11 126.7(5) . . . . ?
C6 C1 C2 F1 -179.6(4) . . . . ?
C6 C1 C2 C3 -0.4(6) . . . . ?
C7 C8 C9 F6 -178.7(4) . . . . ?
C7 C8 C9 C10 -0.9(6) . . . . ?
C8 C7 C12 F8 179.4(4) . . . . ?
C8 C7 C12 C11 -1.4(6) . . . . ?
C8 C9 C10 C4 -179.2(4) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
C9 C10 C11 F7 179.3(4) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C4 C5 F3 -3.5(6) . . . . ?
C10 C4 C5 C6 178.8(4) . . . . ?
C10 C11 C12 F8 179.6(4) . . . . ?
C10 C11 C12 C7 0.5(7) . . . . ?
C12 C7 C8 F5 -176.8(3) . . . . ?
C12 C7 C8 C9 1.7(6) . . . . ?
N1 C13 C14 N2 1.3(6) . . . . ?
N1 C13 C14 C17 -178.1(4) . . . . ?
N2 C15 C16 N1 1.9(7) . . . . ?
N2 C15 C16 C18 -178.1(4) . . . . ?
C13 N1 C16 C15 -1.2(6) . . . . ?
C13 N1 C16 C18 178.9(4) . . . . ?
C14 N2 C15 C16 -1.0(6) . . . . ?
C15 N2 C14 C13 -0.5(6) . . . . ?
C15 N2 C14 C17 178.9(4) . . . . ?
C16 N1 C13 C14 -0.4(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_I2F8bph_22bipy
_database_code_depnum_ccdc_archive 'CCDC 2093043'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
loop_
_audit_author_email
apeloqu@clemson.edu
_chemical_formula_moiety         'C12 F8 I2, C10 H8 N2'
_chemical_formula_sum            'C22 H8 F8 I2 N2'
_chemical_formula_weight         706.118
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.7281(2)
_cell_length_b                   7.6981(3)
_cell_length_c                   36.2272(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.551(1)
_cell_angle_gamma                90
_cell_volume                     2154.43(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      2.25
_exptl_absorpt_coefficient_mu    3.002
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0840 before and 0.0493 after correction.
The Ratio of minimum to maximum transmission is 0.8130.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    2.177
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1325.758
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.056
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.9969
_diffrn_reflns_Laue_measured_fraction_max 0.9933
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            15906
_diffrn_reflns_point_group_measured_fraction_full 0.9969
_diffrn_reflns_point_group_measured_fraction_max 0.9933
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.25
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9933
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              46
_reflns_limit_l_min              0
_reflns_number_gt                4418
_reflns_number_total             4889
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.6555
_refine_diff_density_min         -0.6171
_refine_diff_density_rms         0.1444
_refine_ls_d_res_high            0.7700
_refine_ls_d_res_low             9.0535
_refine_ls_goodness_of_fit_ref   1.0663
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4889
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0249
_refine_ls_restrained_S_all      1.0663
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0157P)²+1.5468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0495
_refine_ls_wR_factor_ref         0.0518
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
I1 I 0.62101(2) 0.20445(2) 0.438867(5) 0.01595(5) Uani 1.000000 .
I2 I -0.02355(2) 0.34500(3) 0.713914(5) 0.01635(5) Uani 1.000000 .
F1 F 0.2354(2) 0.1256(2) 0.46633(4) 0.0238(4) Uani 1.000000 .
F2 F 0.08578(19) 0.1742(2) 0.53068(4) 0.0190(4) Uani 1.000000 .
F3 F 0.60828(19) 0.4039(2) 0.58073(4) 0.0198(4) Uani 1.000000 .
F4 F 0.75738(19) 0.3589(2) 0.51591(5) 0.0223(4) Uani 1.000000 .
F5 F 0.3323(2) 0.1751(2) 0.68896(4) 0.0194(4) Uani 1.000000 .
F6 F 0.4798(2) 0.1477(2) 0.62416(4) 0.0202(4) Uani 1.000000 .
F7 F 0.02796(19) 0.4793(2) 0.56880(4) 0.0175(3) Uani 1.000000 .
F8 F -0.12616(18) 0.4985(2) 0.63346(4) 0.0186(4) Uani 1.000000 .
C1 C 0.5009(3) 0.2422(4) 0.48923(7) 0.0151(6) Uani 1.000000 .
C2 C 0.3292(3) 0.1989(4) 0.49399(7) 0.0147(6) Uani 1.000000 .
C3 C 0.2510(3) 0.2247(4) 0.52746(7) 0.0140(6) Uani 1.000000 .
C4 C 0.3406(3) 0.2928(4) 0.55770(7) 0.0130(5) Uani 1.000000 .
C5 C 0.5142(3) 0.3348(4) 0.55268(8) 0.0155(6) Uani 1.000000 .
C6 C 0.5916(3) 0.3117(4) 0.51927(8) 0.0156(6) Uani 1.000000 .
C7 C 0.0975(3) 0.3365(4) 0.66330(7) 0.0142(6) Uani 1.000000 .
C8 C 0.2540(3) 0.2509(4) 0.65955(7) 0.0129(5) Uani 1.000000 .
C9 C 0.3320(3) 0.2387(4) 0.62602(7) 0.0144(6) Uani 1.000000 .
C10 C 0.2589(3) 0.3123(4) 0.59418(7) 0.0132(6) Uani 1.000000 .
C11 C 0.1038(3) 0.4011(4) 0.59805(7) 0.0132(5) Uani 1.000000 .
C12 C 0.0251(3) 0.4120(4) 0.63176(7) 0.0135(5) Uani 1.000000 .
N1 N 0.8659(3) 0.1537(3) 0.37483(6) 0.0159(5) Uani 1.000000 .
N2 N 0.7382(3) 0.2246(3) 0.27946(6) 0.0161(5) Uani 1.000000 .
C13 C 0.8858(3) 0.1705(3) 0.33816(7) 0.0123(5) Uani 1.000000 .
C14 C 1.0001(4) 0.0908(4) 0.39496(8) 0.0189(6) Uani 1.000000 .
H14 H 0.9873(4) 0.0795(4) 0.42086(8) 0.0227(7) Uiso 1.000000 R
C15 C 1.1563(3) 0.0414(4) 0.38020(8) 0.0187(6) Uani 1.000000 .
H15 H 1.2474(3) -0.0034(4) 0.39553(8) 0.0225(7) Uiso 1.000000 R
C16 C 1.1757(3) 0.0589(4) 0.34252(8) 0.0182(6) Uani 1.000000 .
H16 H 1.2806(3) 0.0260(4) 0.33136(8) 0.0218(7) Uiso 1.000000 R
C17 C 1.0391(3) 0.1254(4) 0.32143(8) 0.0165(6) Uani 1.000000 .
H17 H 1.0502(3) 0.1402(4) 0.29557(8) 0.0198(7) Uiso 1.000000 R
C18 C 0.7356(3) 0.2412(4) 0.31637(7) 0.0126(5) Uani 1.000000 .
C19 C 0.6025(4) 0.2867(4) 0.25969(8) 0.0197(6) Uani 1.000000 .
H19 H 0.6040(4) 0.2760(4) 0.23358(8) 0.0236(8) Uiso 1.000000 R
C20 C 0.4606(4) 0.3654(4) 0.27513(8) 0.0196(6) Uani 1.000000 .
H20 H 0.3663(4) 0.4054(4) 0.26006(8) 0.0235(7) Uiso 1.000000 R
C21 C 0.4598(4) 0.3842(4) 0.31303(8) 0.0201(6) Uani 1.000000 .
H21 H 0.3657(4) 0.4396(4) 0.32457(8) 0.0241(8) Uiso 1.000000 R
C22 C 0.5987(3) 0.3209(4) 0.33391(8) 0.0167(6) Uani 1.000000 .
H22 H 0.6004(3) 0.3317(4) 0.36004(8) 0.0200(7) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.090(3) . ?
I2 C7 2.082(3) . ?
F1 C2 1.345(3) . ?
F2 C3 1.343(3) . ?
F3 C5 1.343(3) . ?
F4 C6 1.341(3) . ?
F5 C8 1.344(3) . ?
F6 C9 1.342(3) . ?
F7 C11 1.340(3) . ?
F8 C12 1.348(3) . ?
C1 C2 1.383(4) . ?
C1 C6 1.386(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.396(4) . ?
C4 C10 1.488(4) . ?
C5 C6 1.376(4) . ?
C7 C8 1.387(4) . ?
C7 C12 1.386(4) . ?
C8 C9 1.374(4) . ?
C9 C10 1.392(4) . ?
C10 C11 1.390(4) . ?
C11 C12 1.382(4) . ?
N1 C13 1.348(3) . ?
N1 C14 1.342(4) . ?
N2 C18 1.344(3) . ?
N2 C19 1.341(4) . ?
C13 C17 1.389(4) . ?
C13 C18 1.489(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(4) . ?
C17 H17 0.9500 . ?
C18 C22 1.392(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(4) . ?
C22 H22 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
C2 C1 I1 121.7(2) . . ?
C6 C1 I1 120.80(19) . . ?
C6 C1 C2 117.5(2) . . ?
C1 C2 F1 120.5(2) . . ?
C3 C2 F1 118.3(2) . . ?
C3 C2 C1 121.2(2) . . ?
C2 C3 F2 118.2(2) . . ?
C4 C3 F2 119.9(2) . . ?
C4 C3 C2 121.8(2) . . ?
C5 C4 C3 116.5(2) . . ?
C10 C4 C3 121.8(2) . . ?
C10 C4 C5 121.7(2) . . ?
C4 C5 F3 119.7(2) . . ?
C6 C5 F3 118.5(2) . . ?
C6 C5 C4 121.8(2) . . ?
C1 C6 F4 119.9(2) . . ?
C5 C6 F4 119.0(2) . . ?
C5 C6 C1 121.2(2) . . ?
C8 C7 I2 121.0(2) . . ?
C12 C7 I2 122.1(2) . . ?
C12 C7 C8 116.9(2) . . ?
C7 C8 F5 120.2(2) . . ?
C9 C8 F5 118.2(2) . . ?
C9 C8 C7 121.6(2) . . ?
C8 C9 F6 118.3(2) . . ?
C10 C9 F6 119.9(2) . . ?
C10 C9 C8 121.8(2) . . ?
C9 C10 C4 121.5(2) . . ?
C11 C10 C4 121.8(2) . . ?
C11 C10 C9 116.7(2) . . ?
C10 C11 F7 120.1(2) . . ?
C12 C11 F7 118.6(2) . . ?
C12 C11 C10 121.4(2) . . ?
C7 C12 F8 120.1(2) . . ?
C11 C12 F8 118.2(2) . . ?
C11 C12 C7 121.7(2) . . ?
C14 N1 C13 117.6(2) . . ?
C19 N2 C18 117.7(2) . . ?
C17 C13 N1 121.9(2) . . ?
C18 C13 N1 116.7(2) . . ?
C18 C13 C17 121.4(2) . . ?
H14 C14 N1 118.06(16) . . ?
C15 C14 N1 123.9(3) . . ?
C15 C14 H14 118.06(16) . . ?
H15 C15 C14 120.89(16) . . ?
C16 C15 C14 118.2(3) . . ?
C16 C15 H15 120.89(16) . . ?
H16 C16 C15 120.70(16) . . ?
C17 C16 C15 118.6(2) . . ?
C17 C16 H16 120.70(16) . . ?
C16 C17 C13 119.9(3) . . ?
H17 C17 C13 120.06(16) . . ?
H17 C17 C16 120.06(16) . . ?
C13 C18 N2 117.4(2) . . ?
C22 C18 N2 121.9(2) . . ?
C22 C18 C13 120.7(2) . . ?
H19 C19 N2 118.09(16) . . ?
C20 C19 N2 123.8(3) . . ?
C20 C19 H19 118.09(17) . . ?
H20 C20 C19 120.91(17) . . ?
C21 C20 C19 118.2(3) . . ?
C21 C20 H20 120.91(16) . . ?
H21 C21 C20 120.58(17) . . ?
C22 C21 C20 118.8(3) . . ?
C22 C21 H21 120.58(17) . . ?
C21 C22 C18 119.5(3) . . ?
H22 C22 C18 120.23(16) . . ?
H22 C22 C21 120.23(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_Br2F8bph_Me4pyrZ
_database_code_depnum_ccdc_archive 'CCDC 2092659'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'Br2 C12 F8, C8 H12 N2'
_chemical_formula_sum            'C20 H12 Br2 F8 N2'
_chemical_formula_weight         592.126
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   13.3837(9)
_cell_length_b                   13.8699(10)
_cell_length_c                   11.1754(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.784(3)
_cell_angle_gamma                90
_cell_volume                     2023.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      2.61
_exptl_absorpt_coefficient_mu    4.090
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0564 before and 0.0409 after correction.
The Ratio of minimum to maximum transmission is 0.8443.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1151.203
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.122
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.9907
_diffrn_reflns_Laue_measured_fraction_max 0.9927
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16444
_diffrn_reflns_point_group_measured_fraction_full 0.9907
_diffrn_reflns_point_group_measured_fraction_max 0.9927
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.14
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9907
_diffrn_measured_fraction_theta_max 0.9927
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2160
_reflns_number_total             2309
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.4013
_refine_diff_density_min         -0.2559
_refine_diff_density_rms         0.0575
_refine_ls_d_res_high            0.7700
_refine_ls_d_res_low             9.5051
_refine_ls_goodness_of_fit_ref   1.0309
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    8
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0179
_refine_ls_R_factor_gt           0.0162
_refine_ls_restrained_S_all      1.0309
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0174P)²+2.8435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0412
_refine_ls_wR_factor_ref         0.0421
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br1 Br 0.582965(10) 0.727061(10) 0.630644(12) 0.01665(5) Uani 1.000000 .
F3 F 0.93755(6) 0.58006(6) 0.83231(8) 0.01809(17) Uani 1.000000 .
F2 F 0.93460(6) 0.88346(6) 0.64012(8) 0.01704(17) Uani 1.000000 .
F4 F 0.73338(6) 0.57548(6) 0.77199(8) 0.01849(18) Uani 1.000000 .
F1 F 0.73071(6) 0.88081(6) 0.58331(8) 0.02024(18) Uani 1.000000 .
N1 N 0.35615(9) 0.74461(8) 0.53550(11) 0.0136(2) Uani 1.000000 .
C4 C 0.94325(10) 0.73077(10) 0.73567(13) 0.0130(3) Uani 1.000000 .
C7 C 0.30086(10) 0.66834(10) 0.48525(12) 0.0131(3) Uani 1.000000 .
C1 C 0.72655(10) 0.72787(10) 0.67540(13) 0.0143(3) Uani 1.000000 .
C9 C 0.30642(10) 0.82617(10) 0.55046(12) 0.0134(3) Uani 1.000000 .
C2 C 0.78091(11) 0.80562(10) 0.64464(13) 0.0143(3) Uani 1.000000 .
C3 C 0.88664(10) 0.80691(10) 0.67404(13) 0.0137(3) Uani 1.000000 .
C8 C 0.35753(11) 0.57741(10) 0.46982(14) 0.0179(3) Uani 1.000000 .
C5 C 0.88781(11) 0.65395(10) 0.76816(12) 0.0137(3) Uani 1.000000 .
C10 C 0.36962(11) 0.91096(10) 0.60721(14) 0.0192(3) Uani 1.000000 .
C6 C 0.78192(11) 0.65212(10) 0.73847(13) 0.0142(3) Uani 1.000000 .
H8a H 0.3506(7) 0.5642(5) 0.38222(14) 0.0269(4) Uiso 1.000000 GR
H8b H 0.43017(19) 0.5851(3) 0.5091(9) 0.0269(4) Uiso 1.000000 GR
H8c H 0.3288(6) 0.52358(18) 0.5081(9) 0.0269(4) Uiso 1.000000 GR
H10a H 0.3529(7) 0.9266(5) 0.6860(5) 0.0288(4) Uiso 1.000000 GR
H10b H 0.44254(11) 0.8948(3) 0.6204(10) 0.0288(4) Uiso 1.000000 GR
H10c H 0.3546(7) 0.9666(3) 0.5522(5) 0.0288(4) Uiso 1.000000 GR


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 1.8756(14) . ?
F3 C5 1.3402(16) . ?
F2 C3 1.3381(16) . ?
F4 C6 1.3417(15) . ?
F1 C2 1.3435(16) . ?
N1 C7 1.3408(18) . ?
N1 C9 1.3416(18) . ?
C4 C4 1.481(3) 2_756 ?
C4 C3 1.3902(19) . ?
C4 C5 1.3918(19) . ?
C7 C9 1.4046(19) 7_566 ?
C7 C8 1.5012(19) . ?
C1 C2 1.386(2) . ?
C1 C6 1.385(2) . ?
C9 C10 1.5045(19) . ?
C2 C3 1.3801(19) . ?
C8 H8a 0.9800 . ?
C8 H8b 0.9800 . ?
C8 H8c 0.9800 . ?
C5 C6 1.382(2) . ?
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
C9 N1 C7 118.32(12) . . ?
C5 C4 C3 116.56(12) . . ?
C9 C7 N1 120.73(13) 7_566 . ?
C8 C7 N1 117.70(12) . . ?
C8 C7 C9 121.57(12) . 7_566 ?
C2 C1 Br1 120.11(11) . . ?
C6 C1 Br1 122.16(10) . . ?
C6 C1 C2 117.73(13) . . ?
C7 C9 N1 120.95(13) 7_566 . ?
C10 C9 N1 117.61(12) . . ?
C10 C9 C7 121.43(13) . 7_566 ?
C1 C2 F1 119.99(12) . . ?
C3 C2 F1 118.82(12) . . ?
C3 C2 C1 121.19(13) . . ?
C4 C3 F2 120.00(12) . . ?
C2 C3 F2 118.27(12) . . ?
C2 C3 C4 121.72(13) . . ?
H8a C8 C7 109.5 . . ?
H8b C8 C7 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 C7 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
C4 C5 F3 119.64(12) . . ?
C6 C5 F3 118.41(12) . . ?
C6 C5 C4 121.93(13) . . ?
H10a C10 C9 109.5 . . ?
H10b C10 C9 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C9 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
C1 C6 F4 120.36(12) . . ?
C5 C6 F4 118.79(12) . . ?
C5 C6 C1 120.85(13) . . ?


_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_Br2F8bph_44Me222bipy
_database_code_depnum_ccdc_archive 'CCDC 2093046'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'Br2 C12 F8, C12 H12 N2'
_chemical_formula_sum            'C24 H12 Br2 F8 N2'
_chemical_formula_weight         640.170
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.7760(4)
_cell_length_b                   10.0737(6)
_cell_length_c                   14.8950(9)
_cell_angle_alpha                81.781(2)
_cell_angle_beta                 78.260(2)
_cell_angle_gamma                83.082(2)
_cell_volume                     1125.59(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      38.06
_cell_measurement_theta_min      2.34
_exptl_absorpt_coefficient_mu    3.684
_exptl_absorpt_correction_T_max  0.7488
_exptl_absorpt_correction_T_min  0.4555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1025 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.6083.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.889
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             623.623
_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.9983
_diffrn_reflns_Laue_measured_fraction_max 0.9989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            74967
_diffrn_reflns_point_group_measured_fraction_full 0.9983
_diffrn_reflns_point_group_measured_fraction_max 0.9989
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.58
_diffrn_reflns_theta_min         2.05
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                5743
_reflns_number_total             6318
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.4231
_refine_diff_density_min         -0.3586
_refine_diff_density_rms         0.0718
_refine_ls_d_res_high            0.7200
_refine_ls_d_res_low             9.9258
_refine_ls_goodness_of_fit_ref   1.0529
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0193
_refine_ls_restrained_S_all      1.0529
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0204P)²+0.6235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0468
_refine_ls_wR_factor_ref         0.0491
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br1 Br 0.627267(17) 0.623785(14) 0.624786(9) 0.01979(4) Uani 1.000000 .
Br2 Br 1.183213(18) -0.036659(14) 0.101166(9) 0.02006(4) Uani 1.000000 .
F7 F 0.78636(11) 0.37726(8) 0.22064(6) 0.02038(16) Uani 1.000000 .
F6 F 1.08232(11) 0.09342(8) 0.43267(5) 0.02005(16) Uani 1.000000 .
F2 F 0.99451(11) 0.51173(8) 0.30977(6) 0.02027(16) Uani 1.000000 .
F3 F 0.70881(11) 0.15825(8) 0.50255(6) 0.02080(16) Uani 1.000000 .
F8 F 0.92995(11) 0.21973(9) 0.08937(5) 0.02213(17) Uani 1.000000 .
F4 F 0.57582(12) 0.32494(9) 0.62949(6) 0.02484(18) Uani 1.000000 .
F1 F 0.86533(12) 0.67794(8) 0.43663(6) 0.02318(17) Uani 1.000000 .
F5 F 1.21099(11) -0.07266(8) 0.30446(6) 0.02144(17) Uani 1.000000 .
N2 N 0.45902(15) 0.79730(12) 0.98122(8) 0.0180(2) Uani 1.000000 .
N1 N 0.50656(15) 0.84559(11) 0.73317(8) 0.0169(2) Uani 1.000000 .
C1 C 0.71689(17) 0.50538(14) 0.53626(9) 0.0173(2) Uani 1.000000 .
C4 C 0.85614(16) 0.32957(13) 0.40212(9) 0.0149(2) Uani 1.000000 .
C3 C 0.89035(17) 0.46393(13) 0.38811(9) 0.0160(2) Uani 1.000000 .
C2 C 0.82336(17) 0.55019(13) 0.45349(9) 0.0171(2) Uani 1.000000 .
C10 C 0.92862(16) 0.23891(13) 0.33091(9) 0.0148(2) Uani 1.000000 .
C11 C 0.89292(17) 0.26699(13) 0.24199(9) 0.0159(2) Uani 1.000000 .
C19 C 0.52748(16) 0.77742(13) 0.89309(9) 0.0148(2) Uani 1.000000 .
C14 C 0.45259(19) 0.93616(14) 0.66691(9) 0.0192(3) Uani 1.000000 .
C17 C 0.37028(17) 0.99911(13) 0.84211(9) 0.0167(2) Uani 1.000000 .
C13 C 0.46475(16) 0.87744(13) 0.82005(9) 0.0147(2) Uani 1.000000 .
C5 C 0.74988(17) 0.28589(13) 0.48555(9) 0.0163(2) Uani 1.000000 .
C9 C 1.03870(17) 0.12280(13) 0.34928(9) 0.0153(2) Uani 1.000000 .
C6 C 0.68086(17) 0.37190(14) 0.55122(9) 0.0177(2) Uani 1.000000 .
C12 C 0.96451(17) 0.18515(14) 0.17459(9) 0.0163(2) Uani 1.000000 .
C7 C 1.07366(17) 0.06941(13) 0.19384(9) 0.0159(2) Uani 1.000000 .
C16 C 0.31285(17) 1.09169(13) 0.77312(10) 0.0176(2) Uani 1.000000 .
C23 C 0.65389(17) 0.67126(13) 0.86983(9) 0.0161(2) Uani 1.000000 .
C15 C 0.35588(18) 1.05774(14) 0.68328(10) 0.0195(3) Uani 1.000000 .
C22 C 0.71482(17) 0.58109(13) 0.93917(9) 0.0175(2) Uani 1.000000 .
C18 C 0.2103(2) 1.22365(14) 0.79392(11) 0.0237(3) Uani 1.000000 .
C8 C 1.10741(17) 0.03860(13) 0.28262(9) 0.0163(2) Uani 1.000000 .
C21 C 0.64501(18) 0.60310(14) 1.02992(10) 0.0200(3) Uani 1.000000 .
C20 C 0.51924(19) 0.71061(15) 1.04703(9) 0.0207(3) Uani 1.000000 .
C24 C 0.8508(2) 0.46544(15) 0.91619(11) 0.0245(3) Uani 1.000000 .
H20 H 0.47275(19) 0.72361(15) 1.10959(9) 0.0249(3) Uiso 1.000000 R
H21 H 0.68311(18) 0.54506(14) 1.07967(10) 0.0240(3) Uiso 1.000000 R
H23 H 0.69849(17) 0.66037(13) 0.80676(9) 0.0194(3) Uiso 1.000000 R
H14 H 0.48262(19) 0.91553(14) 0.60503(9) 0.0230(3) Uiso 1.000000 R
H15 H 0.31923(18) 1.11739(14) 0.63382(10) 0.0234(3) Uiso 1.000000 R
H17 H 0.34520(17) 1.01871(13) 0.90422(9) 0.0201(3) Uiso 1.000000 R
H18a H 0.1774(14) 1.2242(5) 0.86097(11) 0.0355(4) Uiso 1.000000 GR
H18b H 0.2833(6) 1.29758(17) 0.7671(7) 0.0355(4) Uiso 1.000000 GR
H18c H 0.1035(8) 1.2352(6) 0.7672(7) 0.0355(4) Uiso 1.000000 GR
H24a H 0.8331(10) 0.4323(8) 0.8603(5) 0.0367(4) Uiso 1.000000 GR
H24b H 0.9690(2) 0.4959(3) 0.9056(8) 0.0367(4) Uiso 1.000000 GR
H24c H 0.8387(11) 0.3927(5) 0.9677(4) 0.0367(4) Uiso 1.000000 GR


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 1.8769(13) . ?
Br2 C7 1.8699(13) . ?
F7 C11 1.3439(14) . ?
F6 C9 1.3370(14) . ?
F2 C3 1.3410(15) . ?
F3 C5 1.3388(15) . ?
F8 C12 1.3395(14) . ?
F4 C6 1.3409(15) . ?
F1 C2 1.3420(15) . ?
F5 C8 1.3401(15) . ?
N2 C19 1.3461(17) . ?
N2 C20 1.3366(18) . ?
N1 C14 1.3422(17) . ?
N1 C13 1.3437(17) . ?
C1 C2 1.3873(19) . ?
C1 C6 1.384(2) . ?
C4 C3 1.3892(18) . ?
C4 C10 1.4787(18) . ?
C4 C5 1.3907(18) . ?
C3 C2 1.3788(18) . ?
C10 C11 1.3910(17) . ?
C10 C9 1.3922(17) . ?
C11 C12 1.3770(18) . ?
C19 C13 1.4902(17) . ?
C19 C23 1.3943(18) . ?
C14 C15 1.3834(19) . ?
C14 H14 0.9500 . ?
C17 C13 1.3964(18) . ?
C17 C16 1.3919(18) . ?
C17 H17 0.9500 . ?
C5 C6 1.3828(18) . ?
C9 C8 1.3807(18) . ?
C12 C7 1.3881(19) . ?
C7 C8 1.3851(18) . ?
C16 C15 1.3932(19) . ?
C16 C18 1.5035(19) . ?
C23 C22 1.3941(18) . ?
C23 H23 0.9500 . ?
C15 H15 0.9500 . ?
C22 C21 1.3889(19) . ?
C22 C24 1.5040(19) . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C21 C20 1.384(2) . ?
C21 H21 0.9500 . ?
C20 H20 0.9500 . ?
C24 H24a 0.9800 . ?
C24 H24b 0.9800 . ?
C24 H24c 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
C20 N2 C19 116.87(12) . . ?
C13 N1 C14 117.11(12) . . ?
C2 C1 Br1 120.24(10) . . ?
C6 C1 Br1 121.68(10) . . ?
C6 C1 C2 118.08(12) . . ?
C10 C4 C3 121.12(12) . . ?
C5 C4 C3 116.68(12) . . ?
C5 C4 C10 122.20(12) . . ?
C4 C3 F2 119.61(12) . . ?
C2 C3 F2 118.38(12) . . ?
C2 C3 C4 121.99(12) . . ?
C1 C2 F1 120.31(12) . . ?
C3 C2 F1 118.97(12) . . ?
C3 C2 C1 120.71(12) . . ?
C11 C10 C4 121.60(12) . . ?
C9 C10 C4 121.49(11) . . ?
C9 C10 C11 116.90(12) . . ?
C10 C11 F7 119.41(12) . . ?
C12 C11 F7 118.74(11) . . ?
C12 C11 C10 121.85(12) . . ?
C13 C19 N2 116.58(11) . . ?
C23 C19 N2 122.58(12) . . ?
C23 C19 C13 120.83(11) . . ?
C15 C14 N1 123.95(13) . . ?
H14 C14 N1 118.03(8) . . ?
H14 C14 C15 118.03(8) . . ?
C16 C17 C13 120.03(12) . . ?
H17 C17 C13 119.99(8) . . ?
H17 C17 C16 119.99(8) . . ?
C19 C13 N1 116.84(11) . . ?
C17 C13 N1 122.47(12) . . ?
C17 C13 C19 120.67(11) . . ?
C4 C5 F3 119.66(12) . . ?
C6 C5 F3 118.55(12) . . ?
C6 C5 C4 121.76(12) . . ?
C10 C9 F6 119.41(11) . . ?
C8 C9 F6 119.06(11) . . ?
C8 C9 C10 121.51(12) . . ?
C1 C6 F4 120.08(12) . . ?
C5 C6 F4 119.13(12) . . ?
C5 C6 C1 120.78(12) . . ?
C11 C12 F8 119.14(12) . . ?
C7 C12 F8 120.15(12) . . ?
C7 C12 C11 120.70(12) . . ?
C12 C7 Br2 121.12(10) . . ?
C8 C7 Br2 120.67(10) . . ?
C8 C7 C12 118.10(12) . . ?
C15 C16 C17 117.19(12) . . ?
C18 C16 C17 121.74(13) . . ?
C18 C16 C15 121.06(12) . . ?
C22 C23 C19 119.97(12) . . ?
H23 C23 C19 120.02(7) . . ?
H23 C23 C22 120.02(8) . . ?
C16 C15 C14 119.24(12) . . ?
H15 C15 C14 120.38(8) . . ?
H15 C15 C16 120.38(8) . . ?
C21 C22 C23 117.13(12) . . ?
C24 C22 C23 121.16(12) . . ?
C24 C22 C21 121.71(12) . . ?
H18a C18 C16 109.5 . . ?
H18b C18 C16 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C16 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
C9 C8 F5 118.96(11) . . ?
C7 C8 F5 120.13(12) . . ?
C7 C8 C9 120.89(12) . . ?
C20 C21 C22 119.23(12) . . ?
H21 C21 C22 120.38(8) . . ?
H21 C21 C20 120.38(8) . . ?
C21 C20 N2 124.22(13) . . ?
H20 C20 N2 117.89(8) . . ?
H20 C20 C21 117.89(8) . . ?
H24a C24 C22 109.5 . . ?
H24b C24 C22 109.5 . . ?
H24b C24 H24a 109.5 . . ?
H24c C24 C22 109.5 . . ?
H24c C24 H24a 109.5 . . ?
H24c C24 H24b 109.5 . . ?


_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_Br2F4bz_2Me4pyrz
_database_code_depnum_ccdc_archive 'CCDC 2092658'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'Br2 C6 F4, 2(C8 H12 N2)'
_chemical_formula_sum            'C22 H24 Br2 F4 N4'
_chemical_formula_weight         580.263
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.0459(3)
_cell_length_b                   14.8959(6)
_cell_length_c                   11.1802(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.7101(15)
_cell_angle_gamma                90
_cell_volume                     1144.66(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7650
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.446
_cell_measurement_theta_min      2.89
_exptl_absorpt_coefficient_mu    3.591
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1054 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.7481.
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    1.684
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             579.477
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.036
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.9961
_diffrn_reflns_Laue_measured_fraction_max 0.9962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13976
_diffrn_reflns_point_group_measured_fraction_full 0.9961
_diffrn_reflns_point_group_measured_fraction_max 0.9962
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.31
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9962
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -8
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -5
_reflns_number_gt                2048
_reflns_number_total             2362
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.6947
_refine_diff_density_min         -0.5077
_refine_diff_density_rms         0.1100
_refine_ls_d_res_high            0.7965
_refine_ls_d_res_low             8.7998
_refine_ls_goodness_of_fit_ref   1.0569
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.0569
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0206P)²+1.8971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0658
_olex2_refinement_description    
;
1.a Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c), C7(H7a,H7b,H7c), C9(H9a,H9b,H9c), C11(H11a,H11b,H11c)
;
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_refinement_flags_posn
Br1 Br 0.43026(4) 0.217532(16) 0.50261(2) 0.01795(9) Uani 1.000000 .
F1 F 0.7677(2) 0.11396(10) 0.44273(15) 0.0221(3) Uani 1.000000 .
F2 F 0.8283(2) -0.06404(10) 0.43996(15) 0.0219(3) Uani 1.000000 .
N1 N 0.4360(3) 0.41213(14) 0.5018(2) 0.0157(4) Uani 1.000000 .
C1 C 0.4686(4) 0.09272(17) 0.5008(2) 0.0172(5) Uani 1.000000 .
C2 C 0.6337(4) 0.05788(17) 0.4700(2) 0.0169(5) Uani 1.000000 .
C3 C 0.6653(4) -0.03303(17) 0.4693(2) 0.0167(5) Uani 1.000000 .
C4 C 0.4263(4) 0.45532(17) 0.3953(2) 0.0156(5) Uani 1.000000 .
C5 C 0.3411(4) 0.40616(18) 0.2789(2) 0.0215(6) Uani 1.000000 .
H5a H 0.4338(12) 0.4069(11) 0.2252(8) 0.0323(9) Uiso 1.000000 GR
H5b H 0.314(3) 0.3439(4) 0.2981(3) 0.0323(9) Uiso 1.000000 GR
H5c H 0.2200(15) 0.4355(8) 0.2375(9) 0.0323(9) Uiso 1.000000 GR
C6 C 0.5084(4) 0.45591(16) 0.6061(2) 0.0156(5) Uani 1.000000 .
C7 C 0.5170(4) 0.40713(18) 0.7247(2) 0.0209(6) Uani 1.000000 .
H7a H 0.457(2) 0.3479(5) 0.7078(3) 0.0314(8) Uiso 1.000000 GR
H7b H 0.6531(4) 0.3999(11) 0.7680(8) 0.0314(8) Uiso 1.000000 GR
H7c H 0.447(2) 0.4417(6) 0.7759(8) 0.0314(8) Uiso 1.000000 GR
N2 N 0.0492(3) 0.49850(15) 0.6278(2) 0.0207(5) Uani 1.000000 .
C8 C -0.0114(4) 0.42398(18) 0.5632(3) 0.0204(6) Uani 1.000000 .
C9 C -0.0206(4) 0.33871(18) 0.6343(3) 0.0250(6) Uani 1.000000 .
H9a H 0.070(2) 0.2945(5) 0.6130(15) 0.0375(9) Uiso 1.000000 GR
H9b H 0.016(3) 0.3515(3) 0.7223(3) 0.0375(9) Uiso 1.000000 GR
H9c H -0.1533(8) 0.3147(8) 0.6136(15) 0.0375(9) Uiso 1.000000 GR
C10 C 0.0604(4) 0.57456(18) 0.5649(3) 0.0208(6) Uani 1.000000 .
C11 C 0.1250(4) 0.65815(19) 0.6377(3) 0.0256(6) Uani 1.000000 .
H11a H 0.0185(11) 0.7019(6) 0.6235(15) 0.0384(9) Uiso 1.000000 GR
H11b H 0.161(3) 0.6432(3) 0.7251(3) 0.0384(9) Uiso 1.000000 GR
H11c H 0.2376(19) 0.6839(8) 0.6118(14) 0.0384(9) Uiso 1.000000 GR


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 1.879(3) . ?
F1 C2 1.345(3) . ?
F2 C3 1.344(3) . ?
N1 C4 1.342(3) . ?
N1 C6 1.336(3) . ?
C1 C2 1.384(4) . ?
C1 C3 1.390(4) 3_656 ?
C2 C3 1.373(4) . ?
C4 C5 1.498(4) . ?
C4 C6 1.401(4) 3_666 ?
C5 H5a 0.9800 . ?
C5 H5b 0.9800 . ?
C5 H5c 0.9800 . ?
C6 C7 1.502(4) . ?
C7 H7a 0.9800 . ?
C7 H7b 0.9800 . ?
C7 H7c 0.9800 . ?
N2 C8 1.342(3) . ?
N2 C10 1.345(3) . ?
C8 C9 1.507(4) . ?
C8 C10 1.397(4) 3_566 ?
C9 H9a 0.9800 . ?
C9 H9b 0.9800 . ?
C9 H9c 0.9800 . ?
C10 C11 1.502(4) . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 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
C6 N1 C4 118.4(2) . . ?
C2 C1 Br1 120.28(19) . . ?
C3 C1 Br1 121.55(19) 3_656 . ?
C3 C1 C2 118.2(2) 3_656 . ?
C1 C2 F1 119.6(2) . . ?
C3 C2 F1 119.2(2) . . ?
C3 C2 C1 121.2(2) . . ?
C1 C3 F2 120.1(2) 3_656 . ?
C2 C3 F2 119.3(2) . . ?
C2 C3 C1 120.7(2) . 3_656 ?
C5 C4 N1 117.9(2) . . ?
C6 C4 N1 120.6(2) 3_666 . ?
C6 C4 C5 121.4(2) 3_666 . ?
H5a C5 C4 109.5 . . ?
H5b C5 C4 109.5 . . ?
H5b C5 H5a 109.5 . . ?
H5c C5 C4 109.5 . . ?
H5c C5 H5a 109.5 . . ?
H5c C5 H5b 109.5 . . ?
C4 C6 N1 121.0(2) 3_666 . ?
C7 C6 N1 117.9(2) . . ?
C7 C6 C4 121.1(2) . 3_666 ?
H7a C7 C6 109.5 . . ?
H7b C7 C6 109.5 . . ?
H7b C7 H7a 109.5 . . ?
H7c C7 C6 109.5 . . ?
H7c C7 H7a 109.5 . . ?
H7c C7 H7b 109.5 . . ?
C10 N2 C8 117.6(2) . . ?
C9 C8 N2 117.3(2) . . ?
C10 C8 N2 121.1(2) 3_566 . ?
C10 C8 C9 121.6(2) 3_566 . ?
H9a C9 C8 109.5 . . ?
H9b C9 C8 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 C8 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
C8 C10 N2 121.3(2) 3_566 . ?
C11 C10 N2 117.4(3) . . ?
C11 C10 C8 121.3(2) . 3_566 ?
H11a C11 C10 109.5 . . ?
H11b C11 C10 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C10 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 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
Br1 C1 C2 F1 0.8(2) . . . . ?
Br1 C1 C2 C3 179.3(2) . . . . ?
Br1 C1 C3 F2 1.0(2) . . 3_656 3_656 ?
Br1 C1 C3 C2 -179.3(2) . . 3_656 3_656 ?
F1 C2 C1 C3 -178.8(2) . . . 3_656 ?
F1 C2 C3 F2 -0.8(3) . . . . ?
F1 C2 C3 C1 178.8(2) . . . 3_656 ?
F2 C3 C1 C2 179.4(2) . . 3_656 3_656 ?
F2 C3 C2 C1 -179.4(2) . . . . ?
N1 C4 C6 N1 -0.3(2) . . 3_666 3_666 ?
N1 C4 C6 C7 179.5(2) . . 3_666 3_666 ?
N1 C6 C4 N1 0.3(2) . . 3_666 3_666 ?
N1 C6 C4 C5 -178.8(2) . . 3_666 3_666 ?
C1 C2 C3 C1 0.2(3) . . . 3_656 ?
C1 C3 C2 C1 0.2(3) 3_656 . . . ?
N2 C8 C10 N2 -0.1(3) . . 3_566 3_566 ?
N2 C8 C10 C11 179.0(2) . . 3_566 3_566 ?
N2 C10 C8 N2 0.1(3) . . 3_566 3_566 ?
N2 C10 C8 C9 179.0(2) . . 3_566 3_566 ?


_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_2Br2F8bph_dpe
_database_code_depnum_ccdc_archive 'CCDC 2092669'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         '2(Br2 C12 F8), C12 H10 N2'
_chemical_formula_sum            'C36 H10 Br4 F16 N2'
_chemical_formula_weight         1094.082
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.4148(5)
_cell_length_b                   11.4097(7)
_cell_length_c                   21.1980(12)
_cell_angle_alpha                90.035(2)
_cell_angle_beta                 90.010(2)
_cell_angle_gamma                107.163(2)
_cell_volume                     1713.50(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17328
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.68
_exptl_absorpt_coefficient_mu    4.818
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1160 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.7427.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    2.121
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1047.179
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.087
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.9952
_diffrn_reflns_Laue_measured_fraction_max 0.9921
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21406
_diffrn_reflns_point_group_measured_fraction_full 0.9952
_diffrn_reflns_point_group_measured_fraction_max 0.9921
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         2.68
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9952
_diffrn_measured_fraction_theta_max 0.9921
_diffrn_measurement_device_type  'D8 Venture definition'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                6032
_reflns_number_total             7010
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.5197
_refine_diff_density_min         -0.4362
_refine_diff_density_rms         0.1075
_refine_ls_d_res_high            0.7982
_refine_ls_d_res_low             7.6020
_refine_ls_goodness_of_fit_ref   1.0571
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7010
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.0571
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0197P)²+0.5950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0529
_refine_ls_wR_factor_ref         0.0565
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
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_refinement_flags_posn
Br1 Br 0.97618(3) 0.59249(2) 0.695165(11) 0.01506(6) Uani 1.000000 .
Br2 Br 0.71477(3) -0.14748(2) 1.036898(12) 0.02069(7) Uani 1.000000 .
F1 F 0.61196(19) 0.45437(13) 0.76336(7) 0.0192(3) Uani 1.000000 .
F2 F 0.55478(19) 0.27665(13) 0.84934(7) 0.0184(3) Uani 1.000000 .
F3 F 1.1785(2) 0.26198(13) 0.82083(7) 0.0219(3) Uani 1.000000 .
F4 F 1.24076(19) 0.44656(13) 0.73780(7) 0.0211(3) Uani 1.000000 .
F5 F 0.9017(2) 0.02731(13) 0.81338(6) 0.0222(3) Uani 1.000000 .
F6 F 0.8457(2) -0.14885(13) 0.90107(7) 0.0226(3) Uani 1.000000 .
F7 F 0.6912(2) 0.11397(13) 1.04981(6) 0.0212(3) Uani 1.000000 .
F8 F 0.7592(2) 0.29211(12) 0.96354(6) 0.0188(3) Uani 1.000000 .
C13 C 0.9294(3) 0.4574(2) 0.74982(11) 0.0141(5) Uani 1.000000 .
C14 C 0.7551(3) 0.4105(2) 0.77838(11) 0.0142(5) Uani 1.000000 .
C15 C 0.7253(3) 0.3176(2) 0.82215(11) 0.0141(5) Uani 1.000000 .
C16 C 0.8646(3) 0.2642(2) 0.83792(11) 0.0143(5) Uani 1.000000 .
C17 C 1.0375(3) 0.3092(2) 0.80717(11) 0.0159(5) Uani 1.000000 .
C18 C 1.0702(3) 0.4045(2) 0.76476(11) 0.0150(5) Uani 1.000000 .
C19 C 0.8312(3) 0.1654(2) 0.88571(11) 0.0133(5) Uani 1.000000 .
C20 C 0.8522(3) 0.0509(2) 0.87213(11) 0.0155(5) Uani 1.000000 .
C21 C 0.8207(3) -0.0411(2) 0.91650(12) 0.0154(5) Uani 1.000000 .
C22 C 0.7645(3) -0.0219(2) 0.97700(11) 0.0149(5) Uani 1.000000 .
C23 C 0.7447(3) 0.0916(2) 0.99162(11) 0.0155(5) Uani 1.000000 .
C24 C 0.7783(3) 0.1830(2) 0.94705(11) 0.0138(5) Uani 1.000000 .
Br3 Br 0.63480(3) 0.14010(2) 0.587331(11) 0.01752(6) Uani 1.000000 .
Br4 Br 0.24171(4) -0.54179(2) 0.960109(11) 0.01979(7) Uani 1.000000 .
F9 F 0.4995(2) 0.16644(12) 0.72048(7) 0.0224(3) Uani 1.000000 .
F10 F 0.4144(2) 0.00301(13) 0.81425(6) 0.0219(3) Uani 1.000000 .
F11 F 0.5219(2) -0.29815(12) 0.67876(7) 0.0204(3) Uani 1.000000 .
F12 F 0.6189(2) -0.13274(13) 0.58646(7) 0.0230(3) Uani 1.000000 .
F13 F 0.1164(2) -0.21013(13) 0.81548(7) 0.0186(3) Uani 1.000000 .
F14 F 0.0181(2) -0.37998(14) 0.90546(7) 0.0226(3) Uani 1.000000 .
F15 F 0.6110(2) -0.45304(13) 0.88652(7) 0.0207(3) Uani 1.000000 .
F16 F 0.70496(19) -0.28669(13) 0.79382(6) 0.0187(3) Uani 1.000000 .
C25 C 0.5636(3) 0.0211(2) 0.65114(11) 0.0149(5) Uani 1.000000 .
C26 C 0.5077(3) 0.0519(2) 0.70967(12) 0.0157(5) Uani 1.000000 .
C27 C 0.4611(3) -0.0329(2) 0.75781(11) 0.0153(5) Uani 1.000000 .
C28 C 0.4644(3) -0.1528(2) 0.74962(11) 0.0137(5) Uani 1.000000 .
C29 C 0.5180(3) -0.1835(2) 0.69022(11) 0.0148(5) Uani 1.000000 .
C30 C 0.5677(3) -0.0979(2) 0.64226(11) 0.0148(5) Uani 1.000000 .
C31 C 0.4126(3) -0.2447(2) 0.80083(11) 0.0142(5) Uani 1.000000 .
C32 C 0.2394(3) -0.2705(2) 0.83169(11) 0.0142(5) Uani 1.000000 .
C33 C 0.1884(3) -0.3580(2) 0.87830(11) 0.0157(5) Uani 1.000000 .
C34 C 0.3112(3) -0.4225(2) 0.89717(11) 0.0142(5) Uani 1.000000 .
C35 C 0.4863(3) -0.3957(2) 0.86817(11) 0.0153(5) Uani 1.000000 .
C36 C 0.5342(3) -0.3101(2) 0.82081(11) 0.0139(5) Uani 1.000000 .
N1 N 1.0537(3) 0.82707(18) 0.63280(10) 0.0178(5) Uani 1.000000 .
N2 N 1.2835(3) 1.64053(18) 0.48963(10) 0.0176(4) Uani 1.000000 .
C1 C 1.1505(3) 1.2090(2) 0.59117(12) 0.0160(5) Uani 1.000000 .
H1 H 1.1226(3) 1.2577(2) 0.62398(12) 0.0192(6) Uiso 1.000000 R
C2 C 1.2148(3) 1.2647(2) 0.53708(11) 0.0154(5) Uani 1.000000 .
H2 H 1.2475(3) 1.2162(2) 0.50513(11) 0.0184(6) Uiso 1.000000 R
C3 C 1.1190(3) 1.0781(2) 0.60415(11) 0.0149(5) Uani 1.000000 .
C4 C 1.0527(3) 1.0298(2) 0.66316(12) 0.0171(5) Uani 1.000000 .
H4 H 1.0277(3) 1.0816(2) 0.69493(12) 0.0205(6) Uiso 1.000000 R
C5 C 1.0236(4) 0.9064(2) 0.67537(12) 0.0188(5) Uani 1.000000 .
H5 H 0.9799(4) 0.8762(2) 0.71607(12) 0.0225(6) Uiso 1.000000 R
C6 C 1.1164(3) 0.8738(2) 0.57620(12) 0.0177(5) Uani 1.000000 .
H6 H 1.1389(3) 0.8195(2) 0.54523(12) 0.0213(6) Uiso 1.000000 R
C7 C 1.1504(3) 0.9957(2) 0.55984(11) 0.0151(5) Uani 1.000000 .
H7 H 1.1948(3) 1.0232(2) 0.51880(11) 0.0181(6) Uiso 1.000000 R
C8 C 1.2401(3) 1.3942(2) 0.52216(11) 0.0144(5) Uani 1.000000 .
C9 C 1.2707(3) 1.4352(2) 0.46023(12) 0.0180(5) Uani 1.000000 .
H9 H 1.2775(3) 1.3797(2) 0.42750(12) 0.0216(6) Uiso 1.000000 R
C10 C 1.2912(4) 1.5562(2) 0.44645(12) 0.0209(6) Uani 1.000000 .
H10 H 1.3120(4) 1.5816(2) 0.40372(12) 0.0251(7) Uiso 1.000000 R
C11 C 1.2550(4) 1.6010(2) 0.54929(12) 0.0209(6) Uani 1.000000 .
H11 H 1.2488(4) 1.6586(2) 0.58099(12) 0.0251(7) Uiso 1.000000 R
C12 C 1.2340(4) 1.4814(2) 0.56749(12) 0.0200(6) Uani 1.000000 .
H12 H 1.2155(4) 1.4588(2) 0.61067(12) 0.0240(7) Uiso 1.000000 R


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 C13 1.878(2) . ?
Br2 C22 1.868(2) . ?
F1 C14 1.338(3) . ?
F2 C15 1.342(3) . ?
F3 C17 1.342(3) . ?
F4 C18 1.341(3) . ?
F5 C20 1.348(3) . ?
F6 C21 1.337(3) . ?
F7 C23 1.343(3) . ?
F8 C24 1.340(3) . ?
C13 C14 1.384(3) . ?
C13 C18 1.388(3) . ?
C14 C15 1.377(3) . ?
C15 C16 1.386(3) . ?
C16 C17 1.394(3) . ?
C16 C19 1.482(3) . ?
C17 C18 1.376(3) . ?
C19 C20 1.391(3) . ?
C19 C24 1.390(3) . ?
C20 C21 1.377(3) . ?
C21 C22 1.385(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.375(3) . ?
Br3 C25 1.879(2) . ?
Br4 C34 1.867(2) . ?
F9 C26 1.345(3) . ?
F10 C27 1.342(3) . ?
F11 C29 1.339(3) . ?
F12 C30 1.338(3) . ?
F13 C32 1.341(3) . ?
F14 C33 1.343(3) . ?
F15 C35 1.338(3) . ?
F16 C36 1.343(3) . ?
C25 C26 1.386(3) . ?
C25 C30 1.380(3) . ?
C26 C27 1.379(3) . ?
C27 C28 1.387(3) . ?
C28 C29 1.396(3) . ?
C28 C31 1.479(3) . ?
C29 C30 1.383(3) . ?
C31 C32 1.393(3) . ?
C31 C36 1.395(3) . ?
C32 C33 1.376(3) . ?
C33 C34 1.388(3) . ?
C34 C35 1.386(3) . ?
C35 C36 1.373(3) . ?
N1 C5 1.342(3) . ?
N1 C6 1.339(3) . ?
N2 C10 1.341(3) . ?
N2 C11 1.339(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.330(3) . ?
C1 C3 1.468(3) . ?
C2 H2 0.9500 . ?
C2 C8 1.468(3) . ?
C3 C4 1.397(3) . ?
C3 C7 1.395(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(3) . ?
C8 C12 1.393(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.383(3) . ?
C12 H12 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
C14 C13 Br1 120.84(18) . . ?
C18 C13 Br1 121.17(18) . . ?
C18 C13 C14 117.9(2) . . ?
C13 C14 F1 120.3(2) . . ?
C15 C14 F1 118.9(2) . . ?
C15 C14 C13 120.8(2) . . ?
C14 C15 F2 118.6(2) . . ?
C16 C15 F2 119.4(2) . . ?
C16 C15 C14 122.0(2) . . ?
C17 C16 C15 116.7(2) . . ?
C19 C16 C15 121.4(2) . . ?
C19 C16 C17 122.0(2) . . ?
C16 C17 F3 119.5(2) . . ?
C18 C17 F3 118.8(2) . . ?
C18 C17 C16 121.7(2) . . ?
C13 C18 F4 119.8(2) . . ?
C17 C18 F4 119.3(2) . . ?
C17 C18 C13 120.8(2) . . ?
C20 C19 C16 122.3(2) . . ?
C24 C19 C16 121.4(2) . . ?
C24 C19 C20 116.3(2) . . ?
C19 C20 F5 119.4(2) . . ?
C21 C20 F5 118.3(2) . . ?
C21 C20 C19 122.3(2) . . ?
C20 C21 F6 119.7(2) . . ?
C22 C21 F6 120.1(2) . . ?
C22 C21 C20 120.2(2) . . ?
C21 C22 Br2 120.60(18) . . ?
C23 C22 Br2 121.01(18) . . ?
C23 C22 C21 118.4(2) . . ?
C22 C23 F7 120.2(2) . . ?
C24 C23 F7 119.1(2) . . ?
C24 C23 C22 120.8(2) . . ?
C19 C24 F8 119.3(2) . . ?
C23 C24 F8 118.7(2) . . ?
C23 C24 C19 122.0(2) . . ?
C26 C25 Br3 120.14(18) . . ?
C30 C25 Br3 122.03(18) . . ?
C30 C25 C26 117.8(2) . . ?
C25 C26 F9 120.1(2) . . ?
C27 C26 F9 118.8(2) . . ?
C27 C26 C25 121.1(2) . . ?
C26 C27 F10 118.6(2) . . ?
C28 C27 F10 119.6(2) . . ?
C28 C27 C26 121.8(2) . . ?
C29 C28 C27 116.7(2) . . ?
C31 C28 C27 122.1(2) . . ?
C31 C28 C29 121.2(2) . . ?
C28 C29 F11 119.9(2) . . ?
C30 C29 F11 118.6(2) . . ?
C30 C29 C28 121.5(2) . . ?
C25 C30 F12 120.2(2) . . ?
C29 C30 F12 118.7(2) . . ?
C29 C30 C25 121.1(2) . . ?
C32 C31 C28 121.7(2) . . ?
C36 C31 C28 121.9(2) . . ?
C36 C31 C32 116.4(2) . . ?
C31 C32 F13 119.7(2) . . ?
C33 C32 F13 118.3(2) . . ?
C33 C32 C31 122.0(2) . . ?
C32 C33 F14 119.1(2) . . ?
C34 C33 F14 120.4(2) . . ?
C34 C33 C32 120.6(2) . . ?
C33 C34 Br4 120.61(18) . . ?
C35 C34 Br4 121.16(19) . . ?
C35 C34 C33 118.2(2) . . ?
C34 C35 F15 120.0(2) . . ?
C36 C35 F15 119.3(2) . . ?
C36 C35 C34 120.7(2) . . ?
C31 C36 F16 119.0(2) . . ?
C35 C36 F16 119.0(2) . . ?
C35 C36 C31 122.0(2) . . ?
C6 N1 C5 116.2(2) . . ?
C11 N2 C10 116.0(2) . . ?
C2 C1 H1 117.44(15) . . ?
C3 C1 H1 117.44(14) . . ?
C3 C1 C2 125.1(2) . . ?
H2 C2 C1 116.96(15) . . ?
C8 C2 C1 126.1(2) . . ?
C8 C2 H2 116.96(13) . . ?
C4 C3 C1 120.1(2) . . ?
C7 C3 C1 123.4(2) . . ?
C7 C3 C4 116.5(2) . . ?
H4 C4 C3 119.98(15) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 119.98(15) . . ?
C4 C5 N1 123.5(2) . . ?
H5 C5 N1 118.23(14) . . ?
H5 C5 C4 118.23(15) . . ?
H6 C6 N1 117.83(14) . . ?
C7 C6 N1 124.3(2) . . ?
C7 C6 H6 117.83(15) . . ?
C6 C7 C3 119.4(2) . . ?
H7 C7 C3 120.29(14) . . ?
H7 C7 C6 120.29(15) . . ?
C9 C8 C2 120.2(2) . . ?
C12 C8 C2 123.2(2) . . ?
C12 C8 C9 116.6(2) . . ?
H9 C9 C8 120.08(15) . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.08(15) . . ?
C9 C10 N2 124.0(2) . . ?
H10 C10 N2 117.98(14) . . ?
H10 C10 C9 117.98(15) . . ?
H11 C11 N2 118.06(14) . . ?
C12 C11 N2 123.9(2) . . ?
C12 C11 H11 118.06(15) . . ?
C11 C12 C8 119.6(2) . . ?
H12 C12 C8 120.19(14) . . ?
H12 C12 C11 120.19(15) . . ?

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 C13 C14 F1 5.6(2) . . . . ?
Br1 C13 C14 C15 -174.96(19) . . . . ?
Br1 C13 C18 F4 -2.9(2) . . . . ?
Br1 C13 C18 C17 176.89(19) . . . . ?
Br2 C22 C21 F6 -2.2(2) . . . . ?
Br2 C22 C21 C20 178.25(19) . . . . ?
Br2 C22 C23 F7 0.9(2) . . . . ?
Br2 C22 C23 C24 -178.86(19) . . . . ?
F1 C14 C13 C18 -176.8(2) . . . . ?
F1 C14 C15 F2 -1.7(2) . . . . ?
F1 C14 C15 C16 177.1(2) . . . . ?
F2 C15 C14 C13 178.9(2) . . . . ?
F2 C15 C16 C17 178.8(2) . . . . ?
F2 C15 C16 C19 -2.0(3) . . . . ?
F3 C17 C16 C15 179.4(2) . . . . ?
F3 C17 C16 C19 0.1(3) . . . . ?
F3 C17 C18 F4 0.7(3) . . . . ?
F3 C17 C18 C13 -179.1(2) . . . . ?
F4 C18 C13 C14 179.5(2) . . . . ?
F4 C18 C17 C16 178.1(2) . . . . ?
F5 C20 C19 C16 -1.0(3) . . . . ?
F5 C20 C19 C24 179.5(2) . . . . ?
F5 C20 C21 F6 2.2(3) . . . . ?
F5 C20 C21 C22 -178.3(2) . . . . ?
F6 C21 C20 C19 -179.0(2) . . . . ?
F6 C21 C22 C23 178.4(2) . . . . ?
F7 C23 C22 C21 -179.7(2) . . . . ?
F7 C23 C24 F8 1.0(2) . . . . ?
F7 C23 C24 C19 -179.0(2) . . . . ?
F8 C24 C19 C16 -0.8(3) . . . . ?
F8 C24 C19 C20 178.7(2) . . . . ?
F8 C24 C23 C22 -179.3(2) . . . . ?
C13 C14 C15 C16 -2.3(3) . . . . ?
C13 C18 C17 C16 -1.7(3) . . . . ?
C14 C15 C16 C17 -0.0(3) . . . . ?
C14 C15 C16 C19 179.2(2) . . . . ?
C15 C16 C17 C18 2.0(3) . . . . ?
C15 C16 C19 C20 122.7(2) . . . . ?
C15 C16 C19 C24 -57.8(3) . . . . ?
C16 C19 C20 C21 -179.8(2) . . . . ?
C16 C19 C24 C23 179.2(2) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C19 C24 C23 C22 0.7(3) . . . . ?
C20 C21 C22 C23 -1.1(3) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
Br3 C25 C26 F9 1.7(2) . . . . ?
Br3 C25 C26 C27 -177.76(19) . . . . ?
Br3 C25 C30 F12 -1.7(2) . . . . ?
Br3 C25 C30 C29 178.80(19) . . . . ?
Br4 C34 C33 F14 0.5(2) . . . . ?
Br4 C34 C33 C32 -179.70(18) . . . . ?
Br4 C34 C35 F15 -2.1(2) . . . . ?
Br4 C34 C35 C36 178.33(19) . . . . ?
F9 C26 C25 C30 -179.3(2) . . . . ?
F9 C26 C27 F10 -1.8(3) . . . . ?
F9 C26 C27 C28 179.3(2) . . . . ?
F10 C27 C26 C25 177.6(2) . . . . ?
F10 C27 C28 C29 -178.7(2) . . . . ?
F10 C27 C28 C31 1.8(3) . . . . ?
F11 C29 C28 C27 -179.1(2) . . . . ?
F11 C29 C28 C31 0.4(3) . . . . ?
F11 C29 C30 F12 -0.4(3) . . . . ?
F11 C29 C30 C25 179.1(2) . . . . ?
F12 C30 C25 C26 179.4(2) . . . . ?
F12 C30 C29 C28 179.6(2) . . . . ?
F13 C32 C31 C28 -0.8(3) . . . . ?
F13 C32 C31 C36 179.2(2) . . . . ?
F13 C32 C33 F14 0.3(2) . . . . ?
F13 C32 C33 C34 -179.5(2) . . . . ?
F14 C33 C32 C31 -178.9(2) . . . . ?
F14 C33 C34 C35 -179.3(2) . . . . ?
F15 C35 C34 C33 177.8(2) . . . . ?
F15 C35 C36 F16 0.5(2) . . . . ?
F15 C35 C36 C31 -178.1(2) . . . . ?
F16 C36 C31 C28 1.7(3) . . . . ?
F16 C36 C31 C32 -178.3(2) . . . . ?
F16 C36 C35 C34 -179.9(2) . . . . ?
C25 C26 C27 C28 -1.3(3) . . . . ?
C25 C30 C29 C28 -0.9(3) . . . . ?
C26 C27 C28 C29 0.2(3) . . . . ?
C26 C27 C28 C31 -179.3(2) . . . . ?
C27 C28 C29 C30 0.8(3) . . . . ?
C27 C28 C31 C32 55.1(3) . . . . ?
C27 C28 C31 C36 -124.9(2) . . . . ?
C28 C31 C32 C33 178.4(2) . . . . ?
C28 C31 C36 C35 -179.7(2) . . . . ?
C31 C32 C33 C34 1.3(3) . . . . ?
C31 C36 C35 C34 1.5(3) . . . . ?
C32 C33 C34 C35 0.5(3) . . . . ?
C33 C34 C35 C36 -1.8(3) . . . . ?
N1 C5 C4 C3 -0.7(3) . . . . ?
N1 C6 C7 C3 0.1(3) . . . . ?
N2 C10 C9 C8 -0.0(3) . . . . ?
N2 C11 C12 C8 -0.7(3) . . . . ?
C1 C2 C8 C9 -166.6(3) . . . . ?
C1 C2 C8 C12 13.0(3) . . . . ?
C1 C3 C4 C5 -179.9(2) . . . . ?
C1 C3 C7 C6 -179.8(2) . . . . ?
C2 C8 C9 C10 178.9(2) . . . . ?
C2 C8 C12 C11 -178.6(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_Br2F8bph_44bipy
_database_code_depnum_ccdc_archive 'CCDC 2092665'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'Br2 C12 F8, C10 H8 N2'
_chemical_formula_sum            'C22 H8 Br2 F8 N2'
_chemical_formula_weight         612.116
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.7409(4)
_cell_length_b                   11.2944(6)
_cell_length_c                   12.7419(8)
_cell_angle_alpha                73.313(2)
_cell_angle_beta                 72.443(2)
_cell_angle_gamma                89.944(2)
_cell_volume                     1012.9(1)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.94
_exptl_absorpt_coefficient_mu    4.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 22875 reflections, Rint = 0.1433
 (13949 with I > 3sig(I), Rint = 0.1277)
;
_exptl_absorpt_special_details   .
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.007
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             591.613
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.103
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.1433
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.9899
_diffrn_reflns_Laue_measured_fraction_max 0.9883
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22875
_diffrn_reflns_point_group_measured_fraction_full 0.9899
_diffrn_reflns_point_group_measured_fraction_max 0.9883
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.08
_diffrn_reflns_theta_min         3.21
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.9899
_diffrn_measured_fraction_theta_max 0.9883
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -8
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3124
_reflns_number_total             3973
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.8300
_refine_diff_density_min         -1.0177
_refine_diff_density_rms         0.2662
_refine_ls_d_res_high            0.8082
_refine_ls_d_res_low             6.3536
_refine_ls_goodness_of_fit_ref   1.0489
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3973
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.0472
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0139P)²+12.7504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1231
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.006
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.35923(9) 0.60581(6) 0.27954(5) 0.02031(18) Uani 1.000000 . .
Br2 Br -0.09720(9) 0.14431(6) 1.20615(5) 0.02245(19) Uani 1.000000 . .
F1 F 0.4208(5) 0.6882(3) 0.4752(3) 0.0259(9) Uani 1.000000 . .
F2 F 0.3006(5) 0.5786(3) 0.7017(3) 0.0236(8) Uani 1.000000 . .
F3 F 0.0212(5) 0.2438(3) 0.6431(3) 0.0225(8) Uani 1.000000 . .
F4 F 0.1252(5) 0.3598(4) 0.4166(3) 0.0245(9) Uani 1.000000 . .
F5 F -0.1885(5) 0.3955(3) 1.0698(3) 0.0218(8) Uani 1.000000 . .
F6 F -0.0769(5) 0.5077(3) 0.8439(3) 0.0228(8) Uani 1.000000 . .
F7 F 0.2628(5) 0.1722(4) 0.7826(3) 0.0270(9) Uani 1.000000 . .
F8 F 0.1567(5) 0.0596(3) 1.0093(3) 0.0264(9) Uani 1.000000 . .
N1 N 0.4799(8) 0.7215(5) 0.0455(5) 0.0257(13) Uani 1.000000 . .
N2 N 0.7785(8) 1.0258(6) -0.5567(5) 0.0271(14) Uani 1.000000 . .
C1 C 0.2799(8) 0.5262(5) 0.4404(5) 0.0105(12) Uani 1.000000 . U
C2 C 0.3193(8) 0.5803(6) 0.5154(5) 0.0172(13) Uani 1.000000 . .
C3 C 0.2588(9) 0.5224(6) 0.6324(6) 0.0190(14) Uani 1.000000 . .
C4 C 0.1589(9) 0.4072(6) 0.6795(5) 0.0175(14) Uani 1.000000 . .
C5 C 0.1189(8) 0.3532(6) 0.6027(5) 0.0155(13) Uani 1.000000 . .
C6 C 0.1744(8) 0.4133(6) 0.4858(5) 0.0181(14) Uani 1.000000 . .
C7 C -0.0199(8) 0.2253(6) 1.0459(5) 0.0113(12) Uani 1.000000 . U
C8 C -0.0751(9) 0.3399(6) 1.0001(6) 0.0186(14) Uani 1.000000 . .
C9 C -0.0156(8) 0.3955(6) 0.8826(5) 0.0168(13) Uani 1.000000 . .
C10 C 0.0983(8) 0.3441(6) 0.8048(5) 0.0149(13) Uani 1.000000 . .
C11 C 0.1508(8) 0.2277(6) 0.8525(5) 0.0170(13) Uani 1.000000 . .
C12 C 0.0946(9) 0.1698(6) 0.9703(5) 0.0172(13) Uani 1.000000 . .
C13 C 0.4375(9) 0.8367(6) 0.0008(6) 0.0238(15) Uani 1.000000 . .
H13 H 0.3657(9) 0.8765(6) 0.0530(6) 0.0285(18) Uiso 1.000000 R .
C14 C 0.4909(9) 0.9013(6) -0.1157(6) 0.0227(15) Uani 1.000000 . .
H14 H 0.4605(9) 0.9838(6) -0.1416(6) 0.0273(18) Uiso 1.000000 R .
C15 C 0.5897(9) 0.8434(6) -0.1939(5) 0.0191(14) Uani 1.000000 . .
C16 C 0.6311(9) 0.7238(6) -0.1509(6) 0.0216(14) Uani 1.000000 . .
H16 H 0.6969(9) 0.6801(6) -0.2015(6) 0.0259(17) Uiso 1.000000 R .
C17 C 0.5738(9) 0.6683(6) -0.0307(6) 0.0242(15) Uani 1.000000 . .
H17 H 0.6050(9) 0.5865(6) -0.0023(6) 0.0290(18) Uiso 1.000000 R .
C18 C 0.8088(10) 1.0789(7) -0.4816(6) 0.0267(16) Uani 1.000000 . .
H18 H 0.8772(10) 1.1577(7) -0.5109(6) 0.0320(19) Uiso 1.000000 R .
C19 C 0.7447(9) 1.0242(6) -0.3634(6) 0.0235(15) Uani 1.000000 . .
H19 H 0.7653(9) 1.0661(6) -0.3128(6) 0.0282(18) Uiso 1.000000 R .
C20 C 0.6508(9) 0.9081(6) -0.3200(5) 0.0196(14) Uani 1.000000 . .
C21 C 0.6171(9) 0.8527(6) -0.3969(6) 0.0225(15) Uani 1.000000 . .
H21 H 0.5507(9) 0.7734(6) -0.3705(6) 0.0270(18) Uiso 1.000000 R .
C22 C 0.6835(9) 0.9171(7) -0.5140(6) 0.0241(15) Uani 1.000000 . .
H22 H 0.6585(9) 0.8798(7) -0.5665(6) 0.0290(18) Uiso 1.000000 R .


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 1.889(5) . ?
Br2 C7 1.886(5) . ?
F1 C2 1.329(7) . ?
F2 C3 1.336(7) . ?
F3 C5 1.328(7) . ?
F4 C6 1.340(7) . ?
F5 C8 1.342(7) . ?
F6 C9 1.362(7) . ?
F7 C11 1.338(7) . ?
F8 C12 1.348(7) . ?
N1 C13 1.345(9) . ?
N1 C17 1.320(9) . ?
N2 C18 1.340(9) . ?
N2 C22 1.312(9) . ?
C1 C2 1.376(9) . ?
C1 C6 1.385(9) . ?
C2 C3 1.373(9) . ?
C3 C4 1.387(9) . ?
C4 C5 1.397(9) . ?
C4 C10 1.474(8) . ?
C5 C6 1.378(9) . ?
C7 C8 1.384(9) . ?
C7 C12 1.391(9) . ?
C8 C9 1.376(9) . ?
C9 C10 1.377(9) . ?
C10 C11 1.398(9) . ?
C11 C12 1.384(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(9) . ?
C15 C16 1.381(9) . ?
C15 C20 1.486(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.405(9) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.382(10) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(9) . ?
C20 C21 1.388(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(9) . ?
C22 H22 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
C17 N1 C13 115.3(6) . . ?
C22 N2 C18 117.3(6) . . ?
C2 C1 Br1 121.2(4) . . ?
C6 C1 Br1 120.4(5) . . ?
C6 C1 C2 118.4(5) . . ?
C1 C2 F1 120.2(5) . . ?
C3 C2 F1 119.1(6) . . ?
C3 C2 C1 120.8(6) . . ?
C2 C3 F2 118.5(6) . . ?
C4 C3 F2 119.6(6) . . ?
C4 C3 C2 121.9(6) . . ?
C5 C4 C3 117.0(6) . . ?
C10 C4 C3 121.6(6) . . ?
C10 C4 C5 121.4(5) . . ?
C4 C5 F3 119.6(5) . . ?
C6 C5 F3 119.4(5) . . ?
C6 C5 C4 121.0(6) . . ?
C1 C6 F4 120.6(5) . . ?
C5 C6 F4 118.5(6) . . ?
C5 C6 C1 120.9(6) . . ?
C8 C7 Br2 121.5(5) . . ?
C12 C7 Br2 120.2(4) . . ?
C12 C7 C8 118.3(5) . . ?
C7 C8 F5 120.2(5) . . ?
C9 C8 F5 120.3(6) . . ?
C9 C8 C7 119.6(6) . . ?
C8 C9 F6 116.2(5) . . ?
C10 C9 F6 119.8(5) . . ?
C10 C9 C8 124.1(6) . . ?
C9 C10 C4 122.2(5) . . ?
C11 C10 C4 122.2(5) . . ?
C11 C10 C9 115.6(6) . . ?
C10 C11 F7 119.2(5) . . ?
C12 C11 F7 119.0(6) . . ?
C12 C11 C10 121.8(6) . . ?
C7 C12 F8 121.4(5) . . ?
C11 C12 F8 117.9(6) . . ?
C11 C12 C7 120.7(6) . . ?
H13 C13 N1 117.6(4) . . ?
C14 C13 N1 124.8(7) . . ?
C14 C13 H13 117.6(4) . . ?
H14 C14 C13 120.6(4) . . ?
C15 C14 C13 118.7(6) . . ?
C15 C14 H14 120.6(4) . . ?
C16 C15 C14 117.9(6) . . ?
C20 C15 C14 121.2(6) . . ?
C20 C15 C16 120.9(6) . . ?
H16 C16 C15 120.8(4) . . ?
C17 C16 C15 118.5(6) . . ?
C17 C16 H16 120.8(4) . . ?
C16 C17 N1 124.7(6) . . ?
H17 C17 N1 117.6(4) . . ?
H17 C17 C16 117.6(4) . . ?
H18 C18 N2 118.5(4) . . ?
C19 C18 N2 122.9(6) . . ?
C19 C18 H18 118.5(4) . . ?
H19 C19 C18 120.4(4) . . ?
C20 C19 C18 119.1(6) . . ?
C20 C19 H19 120.4(4) . . ?
C19 C20 C15 120.5(6) . . ?
C21 C20 C15 121.1(6) . . ?
C21 C20 C19 118.4(6) . . ?
H21 C21 C20 121.1(4) . . ?
C22 C21 C20 117.9(6) . . ?
C22 C21 H21 121.1(4) . . ?
C21 C22 N2 124.3(7) . . ?
H22 C22 N2 117.8(4) . . ?
H22 C22 C21 117.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 F1 -2.7(5) . . . . ?
Br1 C1 C2 C3 179.1(5) . . . . ?
Br1 C1 C6 F4 -0.9(5) . . . . ?
Br1 C1 C6 C5 178.7(5) . . . . ?
Br2 C7 C8 F5 -1.0(5) . . . . ?
Br2 C7 C8 C9 -179.9(5) . . . . ?
Br2 C7 C12 F8 -1.8(5) . . . . ?
Br2 C7 C12 C11 179.3(5) . . . . ?
F1 C2 C1 C6 179.6(6) . . . . ?
F1 C2 C3 F2 1.7(7) . . . . ?
F1 C2 C3 C4 -177.2(5) . . . . ?
F2 C3 C2 C1 180.0(5) . . . . ?
F2 C3 C4 C5 179.8(6) . . . . ?
F2 C3 C4 C10 -0.5(7) . . . . ?
F3 C5 C4 C3 -179.0(6) . . . . ?
F3 C5 C4 C10 1.4(7) . . . . ?
F3 C5 C6 F4 1.0(6) . . . . ?
F3 C5 C6 C1 -178.6(5) . . . . ?
F4 C6 C1 C2 176.8(6) . . . . ?
F4 C6 C5 C4 -177.0(5) . . . . ?
F5 C8 C7 C12 178.7(6) . . . . ?
F5 C8 C9 F6 0.6(7) . . . . ?
F5 C8 C9 C10 -178.9(5) . . . . ?
F6 C9 C8 C7 179.5(5) . . . . ?
F6 C9 C10 C4 0.6(7) . . . . ?
F6 C9 C10 C11 -178.7(6) . . . . ?
F7 C11 C10 C4 1.4(7) . . . . ?
F7 C11 C10 C9 -179.3(6) . . . . ?
F7 C11 C12 F8 0.2(6) . . . . ?
F7 C11 C12 C7 179.1(5) . . . . ?
F8 C12 C7 C8 178.5(6) . . . . ?
F8 C12 C11 C10 -177.7(5) . . . . ?
N1 C13 C14 C15 2.5(8) . . . . ?
N1 C17 C16 C15 1.0(8) . . . . ?
N2 C18 C19 C20 2.3(9) . . . . ?
N2 C22 C21 C20 1.2(8) . . . . ?
C1 C2 C3 C4 1.0(8) . . . . ?
C1 C6 C5 C4 3.5(7) . . . . ?
C2 C3 C4 C5 -1.2(7) . . . . ?
C2 C3 C4 C10 178.4(6) . . . . ?
C3 C4 C5 C6 -1.0(7) . . . . ?
C3 C4 C10 C9 60.8(7) . . . . ?
C3 C4 C10 C11 -120.0(6) . . . . ?
C4 C10 C9 C8 -179.9(6) . . . . ?
C4 C10 C11 C12 179.3(6) . . . . ?
C7 C8 C9 C10 -0.1(7) . . . . ?
C7 C12 C11 C10 1.2(7) . . . . ?
C8 C9 C10 C11 0.8(7) . . . . ?
C9 C10 C11 C12 -1.4(7) . . . . ?
C13 C14 C15 C16 -0.6(7) . . . . ?
C13 C14 C15 C20 -180.0(6) . . . . ?
C14 C15 C16 C17 -1.0(7) . . . . ?
C14 C15 C20 C19 51.8(7) . . . . ?
C14 C15 C20 C21 -129.1(6) . . . . ?
C15 C20 C19 C18 176.3(6) . . . . ?
C15 C20 C21 C22 -177.9(6) . . . . ?
C18 C19 C20 C21 -2.8(8) . . . . ?
C19 C20 C21 C22 1.2(7) . . . . ?


# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C1 0.0030
C7 0.0030

# start Validation Reply Form
_vrf_PLAT431_Br2F8bph_44bipy     
;
PROBLEM: Short Inter HL..A Contact  Br1      ..N1       .       2.75 Ang.  
RESPONSE: This contact represents a Br...N halogen bond, which is described
further in the manuscript text.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Br2F4bz_quinox
_database_code_depnum_ccdc_archive 'CCDC 2093037'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         '2(Br C3 F2), C8 H6 N2'
_chemical_formula_sum            'C14 H6 Br2 F4 N2'
_chemical_formula_weight         438.018
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.499(1)
_cell_length_b                   6.2670(5)
_cell_length_c                   19.9650(18)
_cell_angle_alpha                90
_cell_angle_beta                 98.291(3)
_cell_angle_gamma                90
_cell_volume                     1423.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      28.323
_cell_measurement_theta_min      3.344
_exptl_absorpt_coefficient_mu    5.734
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0737 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.7569.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.043
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             838.865
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.124
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.9961
_diffrn_reflns_Laue_measured_fraction_max 0.9914
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24244
_diffrn_reflns_point_group_measured_fraction_full 0.9961
_diffrn_reflns_point_group_measured_fraction_max 0.9914
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9914
_diffrn_measurement_device_type  'D8 Venture definition'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -15
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              -11
_reflns_number_gt                3043
_reflns_number_total             3557
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.4400
_refine_diff_density_min         -0.4371
_refine_diff_density_rms         0.0999
_refine_ls_d_res_high            0.7467
_refine_ls_d_res_low             6.0934
_refine_ls_goodness_of_fit_ref   1.0660
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0208
_refine_ls_restrained_S_all      1.0660
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0136P)²+1.4097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0463
_refine_ls_wR_factor_ref         0.0523
_olex2_refinement_description    
;
;
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_refinement_flags_posn
Br1 Br 0.766890(16) 0.26753(3) 0.916677(10) 0.01958(6) Uani 1.000000 .
Br2 Br 0.190555(16) 0.25930(3) 0.613368(10) 0.01980(6) Uani 1.000000 .
F1 F 0.93092(10) 0.11430(18) 1.04218(6) 0.0241(3) Uani 1.000000 .
F3 F 0.21240(10) 0.6840(2) 0.54058(6) 0.0263(3) Uani 1.000000 .
F2 F 0.88151(11) 0.6931(2) 0.88911(6) 0.0291(3) Uani 1.000000 .
F4 F 0.05692(11) 0.88184(18) 0.44934(6) 0.0261(3) Uani 1.000000 .
N1 N 0.55138(14) 0.1132(3) 0.83435(8) 0.0205(3) Uani 1.000000 .
N2 N 0.36423(14) 0.1088(3) 0.72527(9) 0.0209(3) Uani 1.000000 .
C4 C 0.08200(17) 0.3951(3) 0.54761(9) 0.0180(4) Uani 1.000000 .
C6 C 0.02707(17) 0.6936(3) 0.47409(10) 0.0181(4) Uani 1.000000 .
C14 C 0.44733(16) -0.0487(3) 0.73245(10) 0.0171(4) Uani 1.000000 .
C9 C 0.54089(16) -0.0470(3) 0.78719(10) 0.0169(4) Uani 1.000000 .
C2 C 0.90038(16) 0.3993(3) 0.96413(10) 0.0180(4) Uani 1.000000 .
C10 C 0.62417(17) -0.2141(3) 0.79350(11) 0.0237(4) Uani 1.000000 .
C13 C 0.43990(19) -0.2175(3) 0.68487(11) 0.0244(4) Uani 1.000000 .
C1 C 0.96385(17) 0.3047(3) 1.02072(10) 0.0177(4) Uani 1.000000 .
C5 C 0.10788(16) 0.5903(3) 0.52101(10) 0.0183(4) Uani 1.000000 .
C3 C 0.93899(17) 0.5959(3) 0.94414(10) 0.0189(4) Uani 1.000000 .
C12 C 0.5224(2) -0.3764(3) 0.69224(12) 0.0293(5) Uani 1.000000 .
C11 C 0.6145(2) -0.3751(3) 0.74702(12) 0.0298(5) Uani 1.000000 .
C8 C 0.46984(18) 0.2611(3) 0.82599(11) 0.0227(4) Uani 1.000000 .
C7 C 0.37590(18) 0.2585(3) 0.77176(11) 0.0224(4) Uani 1.000000 .
H10 H 0.68692(17) -0.2143(3) 0.83010(11) 0.0284(5) Uiso 1.000000 R
H11 H 0.6705(2) -0.4875(3) 0.75167(12) 0.0358(6) Uiso 1.000000 R
H12 H 0.5175(2) -0.4889(3) 0.66006(12) 0.0351(6) Uiso 1.000000 R
H13 H 0.37781(19) -0.2204(3) 0.64791(11) 0.0293(5) Uiso 1.000000 R
H8 H 0.47404(18) 0.3748(3) 0.85772(11) 0.0272(5) Uiso 1.000000 R
H7 H 0.31908(18) 0.3694(3) 0.76886(11) 0.0268(5) Uiso 1.000000 R


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 1.8754(19) . ?
Br2 C4 1.8799(18) . ?
F1 C1 1.341(2) . ?
F3 C5 1.344(2) . ?
F2 C3 1.344(2) . ?
F4 C6 1.343(2) . ?
N1 C9 1.370(2) . ?
N1 C8 1.312(3) . ?
N2 C14 1.367(2) . ?
N2 C7 1.313(3) . ?
C4 C6 1.383(3) 3_566 ?
C4 C5 1.383(3) . ?
C6 C5 1.382(3) . ?
C14 C9 1.419(3) . ?
C14 C13 1.416(3) . ?
C9 C10 1.412(3) . ?
C2 C1 1.387(3) . ?
C2 C3 1.387(3) . ?
C10 C11 1.365(3) . ?
C10 H10 0.9500 . ?
C13 C12 1.369(3) . ?
C13 H13 0.9500 . ?
C1 C3 1.379(3) 3_767 ?
C12 C11 1.409(3) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C8 C7 1.415(3) . ?
C8 H8 0.9500 . ?
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
C8 N1 C9 116.11(17) . . ?
C7 N2 C14 116.32(17) . . ?
C6 C4 Br2 121.17(14) 3_566 . ?
C5 C4 Br2 120.71(15) . . ?
C5 C4 C6 118.09(17) . 3_566 ?
C4 C6 F4 120.42(17) 3_566 . ?
C5 C6 F4 118.58(17) . . ?
C5 C6 C4 121.00(18) . 3_566 ?
C9 C14 N2 121.09(17) . . ?
C13 C14 N2 119.70(18) . . ?
C13 C14 C9 119.21(18) . . ?
C14 C9 N1 121.12(17) . . ?
C10 C9 N1 119.39(18) . . ?
C10 C9 C14 119.50(18) . . ?
C1 C2 Br1 121.29(14) . . ?
C3 C2 Br1 121.22(14) . . ?
C3 C2 C1 117.49(17) . . ?
C11 C10 C9 120.0(2) . . ?
H10 C10 C9 120.00(12) . . ?
H10 C10 C11 120.00(13) . . ?
C12 C13 C14 119.8(2) . . ?
H13 C13 C14 120.08(12) . . ?
H13 C13 C12 120.08(13) . . ?
C2 C1 F1 120.09(17) . . ?
C3 C1 F1 119.01(17) 3_767 . ?
C3 C1 C2 120.90(17) 3_767 . ?
C4 C5 F3 120.51(17) . . ?
C6 C5 F3 118.58(17) . . ?
C6 C5 C4 120.91(18) . . ?
C2 C3 F2 119.85(17) . . ?
C1 C3 F2 118.54(17) 3_767 . ?
C1 C3 C2 121.61(17) 3_767 . ?
C11 C12 C13 120.7(2) . . ?
H12 C12 C13 119.63(13) . . ?
H12 C12 C11 119.63(13) . . ?
C12 C11 C10 120.7(2) . . ?
H11 C11 C10 119.64(13) . . ?
H11 C11 C12 119.64(13) . . ?
C7 C8 N1 122.81(18) . . ?
H8 C8 N1 118.59(12) . . ?
H8 C8 C7 118.59(11) . . ?
C8 C7 N2 122.54(18) . . ?
H7 C7 N2 118.73(11) . . ?
H7 C7 C8 118.73(12) . . ?


_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_I2F8bph_DABCO
_database_code_depnum_ccdc_archive 'CCDC 2092673'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C12 F8 I2, C6 H12 N2'
_chemical_formula_sum            'C18 H12 F8 I2 N2'
_chemical_formula_weight         662.105
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.5292(11)
_cell_length_b                   10.9229(8)
_cell_length_c                   14.122(1)
_cell_angle_alpha                90
_cell_angle_beta                 108.470(3)
_cell_angle_gamma                90
_cell_volume                     1979.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9239
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      2.41
_exptl_absorpt_coefficient_mu    3.258
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0974 before and 0.0491 after correction.
The Ratio of minimum to maximum transmission is 0.7339.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.222
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1245.715
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.102
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.9958
_diffrn_reflns_Laue_measured_fraction_max 0.9966
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32240
_diffrn_reflns_point_group_measured_fraction_full 0.9958
_diffrn_reflns_point_group_measured_fraction_max 0.9966
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.41
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9958
_diffrn_measured_fraction_theta_max 0.9966
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -17
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -10
_reflns_number_gt                4328
_reflns_number_total             4711
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.8494
_refine_diff_density_min         -0.6215
_refine_diff_density_rms         0.0945
_refine_ls_d_res_high            0.7600
_refine_ls_d_res_low             8.4651
_refine_ls_goodness_of_fit_ref   1.0544
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0191
_refine_ls_restrained_S_all      1.0544
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0144P)²+3.2195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0436
_refine_ls_wR_factor_ref         0.0470
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
I2 I 0.940705(11) 0.707541(13) 0.901423(10) 0.01932(5) Uani 1.000000 .
I1 I 0.054441(11) 0.723235(13) 0.584652(10) 0.01960(5) Uani 1.000000 .
F5 F 0.77658(11) 0.51371(12) 0.75870(10) 0.0234(3) Uani 1.000000 .
F8 F 0.76136(11) 0.88236(12) 0.92929(10) 0.0229(3) Uani 1.000000 .
F4 F 0.21714(11) 0.51017(12) 0.70083(10) 0.0246(3) Uani 1.000000 .
F6 F 0.56969(11) 0.51648(12) 0.67856(10) 0.0240(3) Uani 1.000000 .
F3 F 0.42366(11) 0.50514(12) 0.77686(10) 0.0248(3) Uani 1.000000 .
F1 F 0.23563(11) 0.90796(12) 0.57384(11) 0.0272(3) Uani 1.000000 .
F2 F 0.44253(11) 0.90144(12) 0.64866(10) 0.0242(3) Uani 1.000000 .
F7 F 0.55451(10) 0.88610(12) 0.84729(10) 0.0222(3) Uani 1.000000 .
N2 N -0.35126(15) 0.76809(17) 0.46603(14) 0.0187(4) Uani 1.000000 .
N1 N -0.15200(15) 0.74958(17) 0.52565(14) 0.0187(4) Uani 1.000000 .
C8 C 0.72285(17) 0.60711(19) 0.78257(16) 0.0180(4) Uani 1.000000 .
C12 C 0.71518(19) 0.79141(19) 0.86663(17) 0.0191(4) Uani 1.000000 .
C7 C 0.77583(18) 0.69919(19) 0.84577(16) 0.0185(4) Uani 1.000000 .
C2 C 0.28091(19) 0.8071(2) 0.62434(17) 0.0206(4) Uani 1.000000 .
C6 C 0.27123(18) 0.6081(2) 0.68588(16) 0.0197(4) Uani 1.000000 .
C11 C 0.60834(18) 0.79342(19) 0.82478(16) 0.0191(4) Uani 1.000000 .
C3 C 0.38754(18) 0.80421(19) 0.66279(17) 0.0194(4) Uani 1.000000 .
C1 C 0.21887(18) 0.7102(2) 0.63540(16) 0.0197(4) Uani 1.000000 .
C9 C 0.61590(18) 0.60746(19) 0.74103(16) 0.0186(4) Uani 1.000000 .
C5 C 0.37841(18) 0.60481(19) 0.72483(16) 0.0192(4) Uani 1.000000 .
C15 C -0.19954(18) 0.6307(2) 0.53652(17) 0.0219(4) Uani 1.000000 .
C13 C -0.18926(18) 0.7874(2) 0.41997(17) 0.0216(5) Uani 1.000000 .
C10 C 0.55537(18) 0.70117(19) 0.76032(16) 0.0182(4) Uani 1.000000 .
C4 C 0.44051(18) 0.70285(19) 0.71534(16) 0.0181(4) Uani 1.000000 .
C14 C -0.30992(18) 0.7983(2) 0.38402(17) 0.0226(5) Uani 1.000000 .
C17 C -0.18535(18) 0.8426(2) 0.58597(17) 0.0231(5) Uani 1.000000 .
C18 C -0.30537(19) 0.8519(2) 0.55067(17) 0.0237(5) Uani 1.000000 .
C16 C -0.31959(18) 0.6413(2) 0.49883(17) 0.0218(4) Uani 1.000000 .
H15a H -0.17699(18) 0.5673(2) 0.49765(17) 0.0263(5) Uiso 1.000000 R
H15b H -0.17592(18) 0.6057(2) 0.60756(17) 0.0263(5) Uiso 1.000000 R
H13a H -0.15806(18) 0.8672(2) 0.41225(17) 0.0259(5) Uiso 1.000000 R
H13b H -0.16751(18) 0.7263(2) 0.37870(17) 0.0259(5) Uiso 1.000000 R
H14a H -0.33990(18) 0.7418(2) 0.32736(17) 0.0272(6) Uiso 1.000000 R
H14b H -0.33045(18) 0.8828(2) 0.36057(17) 0.0272(6) Uiso 1.000000 R
H17a H -0.15989(18) 0.8192(2) 0.65736(17) 0.0278(6) Uiso 1.000000 R
H17b H -0.15494(18) 0.9231(2) 0.57874(17) 0.0278(6) Uiso 1.000000 R
H18a H -0.32661(19) 0.9371(2) 0.52992(17) 0.0284(6) Uiso 1.000000 R
H18b H -0.33172(19) 0.8308(2) 0.60650(17) 0.0284(6) Uiso 1.000000 R
H16a H -0.34781(18) 0.6182(2) 0.55304(17) 0.0262(5) Uiso 1.000000 R
H16b H -0.34858(18) 0.5842(2) 0.44237(17) 0.0262(5) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 C7 2.119(2) . ?
I1 C1 2.115(2) . ?
F5 C8 1.356(2) . ?
F8 C12 1.345(2) . ?
F4 C6 1.350(2) . ?
F6 C9 1.344(2) . ?
F3 C5 1.347(2) . ?
F1 C2 1.350(2) . ?
F2 C3 1.347(2) . ?
F7 C11 1.343(2) . ?
N2 C14 1.474(3) . ?
N2 C18 1.477(3) . ?
N2 C16 1.480(3) . ?
N1 C15 1.478(3) . ?
N1 C13 1.475(3) . ?
N1 C17 1.485(3) . ?
C8 C7 1.384(3) . ?
C8 C9 1.378(3) . ?
C12 C7 1.389(3) . ?
C12 C11 1.378(3) . ?
C2 C3 1.371(3) . ?
C2 C1 1.390(3) . ?
C6 C1 1.391(3) . ?
C6 C5 1.379(3) . ?
C11 C10 1.394(3) . ?
C3 C4 1.398(3) . ?
C9 C10 1.391(3) . ?
C5 C4 1.394(3) . ?
C15 C16 1.545(3) . ?
C15 H15a 0.9900 . ?
C15 H15b 0.9900 . ?
C13 C14 1.553(3) . ?
C13 H13a 0.9900 . ?
C13 H13b 0.9900 . ?
C10 C4 1.481(3) . ?
C14 H14a 0.9900 . ?
C14 H14b 0.9900 . ?
C17 C18 1.544(3) . ?
C17 H17a 0.9900 . ?
C17 H17b 0.9900 . ?
C18 H18a 0.9900 . ?
C18 H18b 0.9900 . ?
C16 H16a 0.9900 . ?
C16 H16b 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
C18 N2 C14 109.28(18) . . ?
C16 N2 C14 108.12(18) . . ?
C16 N2 C18 108.73(17) . . ?
C13 N1 C15 109.29(17) . . ?
C17 N1 C15 108.66(17) . . ?
C17 N1 C13 108.69(18) . . ?
C7 C8 F5 119.9(2) . . ?
C9 C8 F5 118.00(19) . . ?
C9 C8 C7 122.1(2) . . ?
C7 C12 F8 119.5(2) . . ?
C11 C12 F8 118.42(19) . . ?
C11 C12 C7 122.1(2) . . ?
C8 C7 I2 122.65(16) . . ?
C12 C7 I2 120.89(16) . . ?
C12 C7 C8 116.3(2) . . ?
C3 C2 F1 118.2(2) . . ?
C1 C2 F1 119.5(2) . . ?
C1 C2 C3 122.4(2) . . ?
C1 C6 F4 120.1(2) . . ?
C5 C6 F4 118.10(19) . . ?
C5 C6 C1 121.7(2) . . ?
C12 C11 F7 118.98(19) . . ?
C10 C11 F7 119.6(2) . . ?
C10 C11 C12 121.4(2) . . ?
C2 C3 F2 118.97(19) . . ?
C4 C3 F2 119.3(2) . . ?
C4 C3 C2 121.8(2) . . ?
C2 C1 I1 121.24(16) . . ?
C6 C1 I1 122.54(16) . . ?
C6 C1 C2 116.1(2) . . ?
C8 C9 F6 118.98(19) . . ?
C10 C9 F6 119.5(2) . . ?
C10 C9 C8 121.5(2) . . ?
C6 C5 F3 118.50(19) . . ?
C4 C5 F3 119.3(2) . . ?
C4 C5 C6 122.1(2) . . ?
C16 C15 N1 110.08(18) . . ?
H15a C15 N1 109.64(12) . . ?
H15a C15 C16 109.64(12) . . ?
H15b C15 N1 109.64(12) . . ?
H15b C15 C16 109.64(12) . . ?
H15b C15 H15a 108.2 . . ?
C14 C13 N1 109.83(18) . . ?
H13a C13 N1 109.70(11) . . ?
H13a C13 C14 109.70(12) . . ?
H13b C13 N1 109.70(12) . . ?
H13b C13 C14 109.70(12) . . ?
H13b C13 H13a 108.2 . . ?
C9 C10 C11 116.6(2) . . ?
C4 C10 C11 121.57(19) . . ?
C4 C10 C9 121.88(19) . . ?
C5 C4 C3 115.9(2) . . ?
C10 C4 C3 121.97(19) . . ?
C10 C4 C5 122.14(19) . . ?
C13 C14 N2 110.31(18) . . ?
H14a C14 N2 109.59(12) . . ?
H14a C14 C13 109.59(12) . . ?
H14b C14 N2 109.59(12) . . ?
H14b C14 C13 109.59(12) . . ?
H14b C14 H14a 108.1 . . ?
C18 C17 N1 109.86(18) . . ?
H17a C17 N1 109.69(11) . . ?
H17a C17 C18 109.69(12) . . ?
H17b C17 N1 109.69(12) . . ?
H17b C17 C18 109.69(12) . . ?
H17b C17 H17a 108.2 . . ?
C17 C18 N2 110.47(18) . . ?
H18a C18 N2 109.56(12) . . ?
H18a C18 C17 109.56(12) . . ?
H18b C18 N2 109.56(12) . . ?
H18b C18 C17 109.56(12) . . ?
H18b C18 H18a 108.1 . . ?
C15 C16 N2 110.24(18) . . ?
H16a C16 N2 109.61(12) . . ?
H16a C16 C15 109.61(12) . . ?
H16b C16 N2 109.61(11) . . ?
H16b C16 C15 109.61(12) . . ?
H16b C16 H16a 108.1 . . ?


_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_I2F8bph_dpe
_database_code_depnum_ccdc_archive 'CCDC 2092670'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C12 F8 I2, C12 H10 N2'
_chemical_formula_sum            'C24 H10 F8 I2 N2'
_chemical_formula_weight         732.156
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.9651(5)
_cell_length_b                   10.8942(7)
_cell_length_c                   14.4024(10)
_cell_angle_alpha                108.756(2)
_cell_angle_beta                 105.483(2)
_cell_angle_gamma                90.273(3)
_cell_volume                     1134.80(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    30125
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.67
_exptl_absorpt_coefficient_mu    2.854
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1225 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.8986.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    2.143
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             690.890
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.036
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.9990
_diffrn_reflns_Laue_measured_fraction_max 0.9991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36775
_diffrn_reflns_point_group_measured_fraction_full 0.9990
_diffrn_reflns_point_group_measured_fraction_max 0.9991
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.67
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                4103
_reflns_number_total             4686
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.7799
_refine_diff_density_min         -0.9158
_refine_diff_density_rms         0.1316
_refine_ls_d_res_high            0.7965
_refine_ls_d_res_low             7.6381
_refine_ls_goodness_of_fit_ref   1.0903
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0236
_refine_ls_restrained_S_all      1.0903
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0110P)²+4.4227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0580
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
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_refinement_flags_posn
I1 I 1.07401(3) 0.84705(2) 1.166030(17) 0.01764(6) Uani 1.000000 .
I2 I 0.64750(3) 0.38941(2) 0.300070(17) 0.01865(6) Uani 1.000000 .
F1 F 0.8838(3) 0.6541(2) 0.45448(16) 0.0224(4) Uani 1.000000 .
F2 F 0.9748(3) 0.76370(19) 0.65806(16) 0.0203(4) Uani 1.000000 .
F3 F 0.6849(3) 0.40163(19) 0.68306(15) 0.0206(4) Uani 1.000000 .
F4 F 0.5694(3) 0.30218(19) 0.47938(16) 0.0214(4) Uani 1.000000 .
F5 F 0.7329(3) 0.82855(19) 0.78242(15) 0.0201(4) Uani 1.000000 .
F6 F 0.8301(3) 0.93616(19) 0.98562(16) 0.0210(4) Uani 1.000000 .
F7 F 1.1560(3) 0.5806(2) 1.01237(16) 0.0211(4) Uani 1.000000 .
F8 F 1.0515(3) 0.47087(19) 0.80886(16) 0.0214(4) Uani 1.000000 .
C13 C 0.7261(4) 0.4732(3) 0.4599(3) 0.0153(7) Uani 1.000000 .
C14 C 0.8288(4) 0.5913(3) 0.5095(3) 0.0165(7) Uani 1.000000 .
C15 C 0.8780(4) 0.6475(3) 0.6144(3) 0.0160(7) Uani 1.000000 .
C16 C 0.8329(4) 0.5858(3) 0.6769(3) 0.0159(7) Uani 1.000000 .
C17 C 0.7329(4) 0.4664(3) 0.6274(3) 0.0177(7) Uani 1.000000 .
C18 C 0.6775(4) 0.4144(3) 0.5227(3) 0.0173(7) Uani 1.000000 .
C19 C 0.8887(4) 0.6462(3) 0.7899(3) 0.0152(7) Uani 1.000000 .
C20 C 0.8385(4) 0.7662(3) 0.8388(3) 0.0155(7) Uani 1.000000 .
C21 C 0.8891(4) 0.8214(3) 0.9432(3) 0.0161(7) Uani 1.000000 .
C22 C 0.9959(4) 0.7621(3) 1.0055(3) 0.0164(7) Uani 1.000000 .
C23 C 1.0490(4) 0.6430(3) 0.9566(3) 0.0171(7) Uani 1.000000 .
C24 C 0.9960(4) 0.5863(3) 0.8520(3) 0.0169(7) Uani 1.000000 .
N1 N 0.1772(4) -0.0536(3) -0.6250(2) 0.0184(6) Uani 1.000000 .
N2 N 0.5394(4) 0.2878(3) 0.0931(2) 0.0195(6) Uani 1.000000 .
C1 C 0.3819(5) 0.1780(4) -0.2335(3) 0.0195(7) Uani 1.000000 .
H1 H 0.3715(5) 0.2467(4) -0.2613(3) 0.0234(9) Uiso 1.000000 R
C2 C 0.3457(5) 0.0552(4) -0.2991(3) 0.0186(7) Uani 1.000000 .
H2 H 0.3576(5) -0.0136(4) -0.2714(3) 0.0224(9) Uiso 1.000000 R
C3 C 0.4365(4) 0.2132(3) -0.1214(3) 0.0164(7) Uani 1.000000 .
C4 C 0.3926(5) 0.3298(3) -0.0613(3) 0.0202(7) Uani 1.000000 .
H4 H 0.3278(5) 0.3863(3) -0.0924(3) 0.0243(9) Uiso 1.000000 R
C5 C 0.4444(5) 0.3624(4) 0.0439(3) 0.0213(7) Uani 1.000000 .
H5 H 0.4114(5) 0.4413(4) 0.0837(3) 0.0256(9) Uiso 1.000000 R
C6 C 0.5809(5) 0.1762(4) 0.0345(3) 0.0204(7) Uani 1.000000 .
H6 H 0.6472(5) 0.1220(4) 0.0674(3) 0.0245(9) Uiso 1.000000 R
C7 C 0.5329(5) 0.1353(3) -0.0712(3) 0.0191(7) Uani 1.000000 .
H7 H 0.5654(5) 0.0549(3) -0.1091(3) 0.0230(9) Uiso 1.000000 R
C8 C 0.2891(5) 0.0205(3) -0.4104(3) 0.0181(7) Uani 1.000000 .
C9 C 0.3394(5) 0.0964(3) -0.4622(3) 0.0194(7) Uani 1.000000 .
H9 H 0.4132(5) 0.1753(3) -0.4250(3) 0.0233(9) Uiso 1.000000 R
C10 C 0.2814(5) 0.0562(4) -0.5674(3) 0.0213(8) Uani 1.000000 .
H10 H 0.3174(5) 0.1093(4) -0.6010(3) 0.0256(9) Uiso 1.000000 R
C11 C 0.1283(5) -0.1269(3) -0.5759(3) 0.0210(7) Uani 1.000000 .
H11 H 0.0535(5) -0.2048(3) -0.6153(3) 0.0252(9) Uiso 1.000000 R
C12 C 0.1814(5) -0.0943(3) -0.4707(3) 0.0204(7) Uani 1.000000 .
H12 H 0.1447(5) -0.1501(3) -0.4394(3) 0.0244(9) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C22 2.106(3) . ?
I2 C13 2.097(3) . ?
F1 C14 1.349(4) . ?
F2 C15 1.346(4) . ?
F3 C17 1.346(4) . ?
F4 C18 1.355(4) . ?
F5 C20 1.351(4) . ?
F6 C21 1.351(4) . ?
F7 C23 1.351(4) . ?
F8 C24 1.346(4) . ?
C13 C14 1.387(5) . ?
C13 C18 1.391(5) . ?
C14 C15 1.377(5) . ?
C15 C16 1.398(5) . ?
C16 C17 1.387(5) . ?
C16 C19 1.483(5) . ?
C17 C18 1.373(5) . ?
C19 C20 1.389(5) . ?
C19 C24 1.389(5) . ?
C20 C21 1.371(5) . ?
C21 C22 1.384(5) . ?
C22 C23 1.391(5) . ?
C23 C24 1.374(5) . ?
N1 C10 1.339(5) . ?
N1 C11 1.339(5) . ?
N2 C5 1.351(5) . ?
N2 C6 1.339(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.343(5) . ?
C1 C3 1.472(5) . ?
C2 H2 0.9500 . ?
C2 C8 1.463(5) . ?
C3 C4 1.394(5) . ?
C3 C7 1.392(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.383(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(5) . ?
C8 C12 1.395(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.383(5) . ?
C12 H12 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
C14 C13 I2 122.0(2) . . ?
C18 C13 I2 122.2(3) . . ?
C18 C13 C14 115.8(3) . . ?
C13 C14 F1 119.7(3) . . ?
C15 C14 F1 118.3(3) . . ?
C15 C14 C13 122.0(3) . . ?
C14 C15 F2 119.3(3) . . ?
C16 C15 F2 119.0(3) . . ?
C16 C15 C14 121.7(3) . . ?
C17 C16 C15 116.3(3) . . ?
C19 C16 C15 121.3(3) . . ?
C19 C16 C17 122.4(3) . . ?
C16 C17 F3 119.4(3) . . ?
C18 C17 F3 119.1(3) . . ?
C18 C17 C16 121.5(3) . . ?
C13 C18 F4 119.1(3) . . ?
C17 C18 F4 118.3(3) . . ?
C17 C18 C13 122.6(3) . . ?
C20 C19 C16 121.8(3) . . ?
C24 C19 C16 121.6(3) . . ?
C24 C19 C20 116.6(3) . . ?
C19 C20 F5 119.3(3) . . ?
C21 C20 F5 119.0(3) . . ?
C21 C20 C19 121.7(3) . . ?
C20 C21 F6 118.4(3) . . ?
C22 C21 F6 119.7(3) . . ?
C22 C21 C20 121.9(3) . . ?
C21 C22 I1 122.0(2) . . ?
C23 C22 I1 121.6(3) . . ?
C23 C22 C21 116.5(3) . . ?
C22 C23 F7 119.8(3) . . ?
C24 C23 F7 118.5(3) . . ?
C24 C23 C22 121.8(3) . . ?
C19 C24 F8 119.3(3) . . ?
C23 C24 F8 119.2(3) . . ?
C23 C24 C19 121.5(3) . . ?
C11 N1 C10 117.1(3) . . ?
C6 N2 C5 116.6(3) . . ?
C2 C1 H1 117.8(2) . . ?
C3 C1 H1 117.8(2) . . ?
C3 C1 C2 124.3(3) . . ?
H2 C2 C1 117.9(2) . . ?
C8 C2 C1 124.2(3) . . ?
C8 C2 H2 117.9(2) . . ?
C4 C3 C1 119.6(3) . . ?
C7 C3 C1 122.9(3) . . ?
C7 C3 C4 117.5(3) . . ?
H4 C4 C3 120.3(2) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3(2) . . ?
C4 C5 N2 123.4(3) . . ?
H5 C5 N2 118.3(2) . . ?
H5 C5 C4 118.3(2) . . ?
H6 C6 N2 118.1(2) . . ?
C7 C6 N2 123.9(3) . . ?
C7 C6 H6 118.1(2) . . ?
C6 C7 C3 119.3(3) . . ?
H7 C7 C3 120.4(2) . . ?
H7 C7 C6 120.4(2) . . ?
C9 C8 C2 123.3(3) . . ?
C12 C8 C2 120.1(3) . . ?
C12 C8 C9 116.5(3) . . ?
H9 C9 C8 120.2(2) . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.2(2) . . ?
C9 C10 N1 123.6(3) . . ?
H10 C10 N1 118.2(2) . . ?
H10 C10 C9 118.2(2) . . ?
H11 C11 N1 118.5(2) . . ?
C12 C11 N1 123.1(3) . . ?
C12 C11 H11 118.5(2) . . ?
C11 C12 C8 120.0(3) . . ?
H12 C12 C8 120.0(2) . . ?
H12 C12 C11 120.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C22 C21 F6 -1.0(3) . . . . ?
I1 C22 C21 C20 179.9(3) . . . . ?
I1 C22 C23 F7 -1.3(3) . . . . ?
I1 C22 C23 C24 178.9(3) . . . . ?
I2 C13 C14 F1 -1.3(3) . . . . ?
I2 C13 C14 C15 178.9(2) . . . . ?
I2 C13 C18 F4 -3.1(3) . . . . ?
I2 C13 C18 C17 177.9(3) . . . . ?
F1 C14 C13 C18 179.1(3) . . . . ?
F1 C14 C15 F2 1.6(3) . . . . ?
F1 C14 C15 C16 -177.1(3) . . . . ?
F2 C15 C14 C13 -178.6(3) . . . . ?
F2 C15 C16 C17 179.9(3) . . . . ?
F2 C15 C16 C19 0.3(4) . . . . ?
F3 C17 C16 C15 180.0(3) . . . . ?
F3 C17 C16 C19 -0.5(4) . . . . ?
F3 C17 C18 F4 3.0(3) . . . . ?
F3 C17 C18 C13 -177.9(3) . . . . ?
F4 C18 C13 C14 176.5(3) . . . . ?
F4 C18 C17 C16 -175.1(3) . . . . ?
F5 C20 C19 C16 1.5(4) . . . . ?
F5 C20 C19 C24 -179.4(3) . . . . ?
F5 C20 C21 F6 0.4(3) . . . . ?
F5 C20 C21 C22 179.4(3) . . . . ?
F6 C21 C20 C19 -177.6(3) . . . . ?
F6 C21 C22 C23 178.8(3) . . . . ?
F7 C23 C22 C21 178.8(3) . . . . ?
F7 C23 C24 F8 0.2(3) . . . . ?
F7 C23 C24 C19 -178.8(3) . . . . ?
F8 C24 C19 C16 0.3(4) . . . . ?
F8 C24 C19 C20 -178.8(3) . . . . ?
F8 C24 C23 C22 -180.0(3) . . . . ?
C13 C14 C15 C16 2.7(4) . . . . ?
C13 C18 C17 C16 3.9(4) . . . . ?
C14 C15 C16 C17 -1.4(4) . . . . ?
C14 C15 C16 C19 179.1(3) . . . . ?
C15 C16 C17 C18 -1.8(4) . . . . ?
C15 C16 C19 C20 60.6(4) . . . . ?
C15 C16 C19 C24 -118.5(3) . . . . ?
C16 C19 C20 C21 179.5(3) . . . . ?
C16 C19 C24 C23 179.3(3) . . . . ?
C19 C20 C21 C22 1.4(4) . . . . ?
C19 C24 C23 C22 1.0(4) . . . . ?
C20 C21 C22 C23 -0.2(4) . . . . ?
C21 C22 C23 C24 -1.0(4) . . . . ?
N1 C10 C9 C8 0.1(4) . . . . ?
N1 C11 C12 C8 0.9(4) . . . . ?
N2 C5 C4 C3 1.2(4) . . . . ?
N2 C6 C7 C3 0.4(4) . . . . ?
C1 C2 C8 C9 30.3(4) . . . . ?
C1 C2 C8 C12 -150.6(4) . . . . ?
C1 C3 C4 C5 -180.0(3) . . . . ?
C1 C3 C7 C6 179.2(3) . . . . ?
C2 C8 C9 C10 179.4(3) . . . . ?
C2 C8 C12 C11 -179.9(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_Br2F8bph_DABCO
_database_code_depnum_ccdc_archive 'CCDC 2092671'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'Br2 C12 F8, C6 H12 N2'
_chemical_formula_sum            'C18 H12 Br2 F8 N2'
_chemical_formula_weight         568.104
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.1047(10)
_cell_length_b                   10.8097(8)
_cell_length_c                   14.1460(11)
_cell_angle_alpha                90
_cell_angle_beta                 107.369(3)
_cell_angle_gamma                90
_cell_volume                     1912.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.409
_cell_measurement_theta_min      2.490
_exptl_absorpt_coefficient_mu    4.322
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.7036.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1103.182
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.047
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9972
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27928
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.9972
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.41
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9972
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -16
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -9
_reflns_number_gt                3134
_reflns_number_total             3921
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.6002
_refine_diff_density_min         -0.6706
_refine_diff_density_rms         0.1403
_refine_ls_d_res_high            0.7990
_refine_ls_d_res_low             8.4382
_refine_ls_goodness_of_fit_ref   1.0284
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3921
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.0284
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0202P)²+2.3619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0661
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C13(H13a,H13b), C14(H14a,H14b), C17(H17a,H17b), C18(H18a,
 H18b), C16(H16a,H16b)
;
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_refinement_flags_posn
Br2 Br 0.93306(2) 0.70195(3) 0.89838(2) 0.01838(9) Uani 1.000000 .
Br1 Br 0.06474(2) 0.71552(3) 0.58857(2) 0.01897(9) Uani 1.000000 .
F5 F 0.78953(13) 0.50747(15) 0.76024(12) 0.0206(4) Uani 1.000000 .
F8 F 0.76403(13) 0.87560(15) 0.93119(12) 0.0210(4) Uani 1.000000 .
F4 F 0.20778(13) 0.50256(15) 0.70212(13) 0.0215(4) Uani 1.000000 .
F6 F 0.57730(13) 0.50494(15) 0.68094(12) 0.0204(4) Uani 1.000000 .
F3 F 0.41969(13) 0.49414(15) 0.77843(12) 0.0211(4) Uani 1.000000 .
F1 F 0.23489(14) 0.89993(15) 0.57252(13) 0.0250(4) Uani 1.000000 .
F2 F 0.44718(13) 0.89045(15) 0.64817(13) 0.0223(4) Uani 1.000000 .
F7 F 0.55158(13) 0.87479(15) 0.84945(12) 0.0212(4) Uani 1.000000 .
N2 N -0.35259(19) 0.7675(2) 0.46549(18) 0.0177(5) Uani 1.000000 .
N1 N -0.14868(19) 0.7482(2) 0.52621(18) 0.0173(5) Uani 1.000000 .
C8 C 0.7319(2) 0.5990(3) 0.7835(2) 0.0173(6) Uani 1.000000 .
C12 C 0.7187(2) 0.7844(3) 0.8684(2) 0.0176(6) Uani 1.000000 .
C7 C 0.7824(2) 0.6930(3) 0.8470(2) 0.0159(6) Uani 1.000000 .
C2 C 0.2795(2) 0.7989(3) 0.6239(2) 0.0180(6) Uani 1.000000 .
C6 C 0.2658(2) 0.5996(3) 0.6874(2) 0.0164(6) Uani 1.000000 .
C11 C 0.6092(2) 0.7832(2) 0.8266(2) 0.0160(6) Uani 1.000000 .
C3 C 0.3891(2) 0.7936(3) 0.6627(2) 0.0176(6) Uani 1.000000 .
C1 C 0.2153(2) 0.7026(3) 0.6361(2) 0.0176(6) Uani 1.000000 .
C9 C 0.6217(2) 0.5976(3) 0.7425(2) 0.0168(6) Uani 1.000000 .
C5 C 0.3759(2) 0.5947(3) 0.7261(2) 0.0165(6) Uani 1.000000 .
C15 C -0.1979(2) 0.6286(3) 0.5344(2) 0.0194(6) Uani 1.000000 .
H15a H -0.1735(2) 0.5658(3) 0.4950(2) 0.0233(8) Uiso 1.000000 R
H15b H -0.1755(2) 0.6013(3) 0.6044(2) 0.0233(8) Uiso 1.000000 R
C13 C -0.1835(2) 0.7892(3) 0.4224(2) 0.0187(6) Uani 1.000000 .
H13a H -0.1509(2) 0.8704(3) 0.4168(2) 0.0224(7) Uiso 1.000000 R
H13b H -0.1592(2) 0.7291(3) 0.3809(2) 0.0224(7) Uiso 1.000000 R
C10 C 0.5580(2) 0.6902(3) 0.7622(2) 0.0159(6) Uani 1.000000 .
C4 C 0.4406(2) 0.6923(3) 0.7160(2) 0.0163(6) Uani 1.000000 .
C14 C -0.3071(2) 0.8002(3) 0.3849(2) 0.0201(6) Uani 1.000000 .
H14a H -0.3359(2) 0.7441(3) 0.3279(2) 0.0241(8) Uiso 1.000000 R
H14b H -0.3276(2) 0.8859(3) 0.3625(2) 0.0241(8) Uiso 1.000000 R
C17 C -0.1847(2) 0.8399(3) 0.5867(2) 0.0217(7) Uani 1.000000 .
H17a H -0.1612(2) 0.8143(3) 0.6571(2) 0.0260(8) Uiso 1.000000 R
H17b H -0.1524(2) 0.9215(3) 0.5815(2) 0.0260(8) Uiso 1.000000 R
C18 C -0.3086(2) 0.8503(3) 0.5499(2) 0.0216(7) Uani 1.000000 .
H18a H -0.3294(2) 0.9367(3) 0.5298(2) 0.0260(8) Uiso 1.000000 R
H18b H -0.3383(2) 0.8282(3) 0.6043(2) 0.0260(8) Uiso 1.000000 R
C16 C -0.3215(2) 0.6396(3) 0.4964(2) 0.0202(6) Uani 1.000000 .
H16a H -0.3522(2) 0.6153(3) 0.5497(2) 0.0243(8) Uiso 1.000000 R
H16b H -0.3500(2) 0.5830(3) 0.4397(2) 0.0243(8) Uiso 1.000000 R


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 C7 1.892(3) . ?
Br1 C1 1.890(3) . ?
F5 C8 1.344(3) . ?
F8 C12 1.342(3) . ?
F4 C6 1.347(3) . ?
F6 C9 1.341(3) . ?
F3 C5 1.344(3) . ?
F1 C2 1.345(3) . ?
F2 C3 1.346(3) . ?
F7 C11 1.342(3) . ?
N2 C14 1.479(4) . ?
N2 C18 1.466(4) . ?
N2 C16 1.470(4) . ?
N1 C15 1.464(4) . ?
N1 C13 1.470(4) . ?
N1 C17 1.476(4) . ?
C8 C7 1.386(4) . ?
C8 C9 1.386(4) . ?
C12 C7 1.384(4) . ?
C12 C11 1.379(4) . ?
C2 C3 1.377(4) . ?
C2 C1 1.381(4) . ?
C6 C1 1.385(4) . ?
C6 C5 1.384(4) . ?
C11 C10 1.388(4) . ?
C3 C4 1.385(4) . ?
C9 C10 1.384(4) . ?
C5 C4 1.386(4) . ?
C15 H15a 0.9900 . ?
C15 H15b 0.9900 . ?
C15 C16 1.552(4) . ?
C13 H13a 0.9900 . ?
C13 H13b 0.9900 . ?
C13 C14 1.551(4) . ?
C10 C4 1.482(4) . ?
C14 H14a 0.9900 . ?
C14 H14b 0.9900 . ?
C17 H17a 0.9900 . ?
C17 H17b 0.9900 . ?
C17 C18 1.555(4) . ?
C18 H18a 0.9900 . ?
C18 H18b 0.9900 . ?
C16 H16a 0.9900 . ?
C16 H16b 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
C18 N2 C14 109.3(2) . . ?
C16 N2 C14 108.3(2) . . ?
C16 N2 C18 109.0(2) . . ?
C13 N1 C15 109.5(2) . . ?
C17 N1 C15 108.8(2) . . ?
C17 N1 C13 108.6(2) . . ?
C7 C8 F5 120.2(3) . . ?
C9 C8 F5 118.7(3) . . ?
C9 C8 C7 121.0(3) . . ?
C7 C12 F8 119.5(3) . . ?
C11 C12 F8 119.3(2) . . ?
C11 C12 C7 121.2(3) . . ?
C8 C7 Br2 121.9(2) . . ?
C12 C7 Br2 120.5(2) . . ?
C12 C7 C8 117.5(3) . . ?
C3 C2 F1 118.9(3) . . ?
C1 C2 F1 119.8(3) . . ?
C1 C2 C3 121.3(3) . . ?
C1 C6 F4 120.3(3) . . ?
C5 C6 F4 118.7(3) . . ?
C5 C6 C1 121.1(3) . . ?
C12 C11 F7 118.6(2) . . ?
C10 C11 F7 119.7(3) . . ?
C10 C11 C12 121.7(3) . . ?
C2 C3 F2 118.4(3) . . ?
C4 C3 F2 119.5(3) . . ?
C4 C3 C2 122.1(3) . . ?
C2 C1 Br1 120.7(2) . . ?
C6 C1 Br1 122.0(2) . . ?
C6 C1 C2 117.3(3) . . ?
C8 C9 F6 118.4(2) . . ?
C10 C9 F6 120.0(3) . . ?
C10 C9 C8 121.5(3) . . ?
C6 C5 F3 118.1(2) . . ?
C4 C5 F3 119.9(3) . . ?
C4 C5 C6 121.9(3) . . ?
H15a C15 N1 109.65(15) . . ?
H15b C15 N1 109.65(15) . . ?
H15b C15 H15a 108.2 . . ?
C16 C15 N1 110.1(2) . . ?
C16 C15 H15a 109.65(16) . . ?
C16 C15 H15b 109.65(15) . . ?
H13a C13 N1 109.60(15) . . ?
H13b C13 N1 109.60(15) . . ?
H13b C13 H13a 108.1 . . ?
C14 C13 N1 110.3(2) . . ?
C14 C13 H13a 109.60(16) . . ?
C14 C13 H13b 109.60(16) . . ?
C9 C10 C11 117.0(3) . . ?
C4 C10 C11 120.9(3) . . ?
C4 C10 C9 122.1(3) . . ?
C5 C4 C3 116.3(3) . . ?
C10 C4 C3 121.6(3) . . ?
C10 C4 C5 122.0(3) . . ?
C13 C14 N2 109.7(2) . . ?
H14a C14 N2 109.72(15) . . ?
H14a C14 C13 109.72(16) . . ?
H14b C14 N2 109.72(15) . . ?
H14b C14 C13 109.72(15) . . ?
H14b C14 H14a 108.2 . . ?
H17a C17 N1 109.73(15) . . ?
H17b C17 N1 109.73(15) . . ?
H17b C17 H17a 108.2 . . ?
C18 C17 N1 109.7(2) . . ?
C18 C17 H17a 109.73(16) . . ?
C18 C17 H17b 109.73(16) . . ?
C17 C18 N2 110.3(2) . . ?
H18a C18 N2 109.60(16) . . ?
H18a C18 C17 109.60(16) . . ?
H18b C18 N2 109.60(15) . . ?
H18b C18 C17 109.60(16) . . ?
H18b C18 H18a 108.1 . . ?
C15 C16 N2 110.1(2) . . ?
H16a C16 N2 109.64(15) . . ?
H16a C16 C15 109.64(15) . . ?
H16b C16 N2 109.64(15) . . ?
H16b C16 C15 109.64(16) . . ?
H16b C16 H16a 108.2 . . ?


# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT431_Br2F8bph_DABCO      
;
PROBLEM: Short Inter HL..A Contact  Br1      ..N1       .       2.69 Ang.  
RESPONSE: This contact represents a Br...N halogen bond, which is discussed
further in the manuscript text.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I2F4bz_44Me222bipy
_database_code_depnum_ccdc_archive 'CCDC 2093045'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C6 F4 I2, C12 H12 N2'
_chemical_formula_sum            'C18 H12 F4 I2 N2'
_chemical_formula_weight         586.112
_chemical_absolute_configuration .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A e a 2'
_space_group_name_Hall           ' A 2 -2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z
3 -x+1/2,y+1/2,z
4 x+1/2,-y+1/2,z
5 x,y+1/2,z+1/2
6 -x,-y+1/2,z+1/2
7 -x+1/2,y+1,z+1/2
8 x+1/2,-y+1,z+1/2

_symmetry_Int_Tables_number      41
_cell_length_a                   13.1529(17)
_cell_length_b                   18.502(3)
_cell_length_c                   15.239(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3708.5(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9802
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.281
_cell_measurement_theta_min      2.322
_exptl_absorpt_coefficient_mu    3.434
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1174 before and 0.0635 after correction.
The Ratio of minimum to maximum transmission is 0.8273.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.100
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             2202.877
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.051
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33906
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9987
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.20
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.998
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              24
_reflns_limit_k_min              -24
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                4070
_reflns_number_total             4596
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.0112
_refine_diff_density_min         -0.9796
_refine_diff_density_rms         0.1314
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_d_res_high            0.7498
_refine_ls_d_res_low             9.2509
_refine_ls_goodness_of_fit_ref   1.0610
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4596
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0239
_refine_ls_restrained_S_all      1.0610
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0000P)²+16.6912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0447
_refine_ls_wR_factor_ref         0.0503
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C15(H15), C9(H9), C11(H11), C8(H8), C14(H14)
1.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C12(H12a,H12b,H12c)
;
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_refinement_flags_posn
I1 I 0.40014(2) 0.614624(14) 0.511469(16) 0.02092(6) Uani 1.000000 .
I2 I 0.401624(19) 0.687267(14) 0.061379(16) 0.01998(6) Uani 1.000000 .
F4 F 0.3946(2) 0.51105(15) 0.3419(2) 0.0239(6) Uani 1.000000 .
F1 F 0.4086(2) 0.76196(14) 0.40201(17) 0.0221(6) Uani 1.000000 .
F2 F 0.41323(19) 0.78943(14) 0.23045(19) 0.0219(6) Uani 1.000000 .
F3 F 0.3972(2) 0.53873(14) 0.17006(18) 0.0244(6) Uani 1.000000 .
N1 N 0.3704(3) 0.5809(2) 0.7038(3) 0.0220(9) Uani 1.000000 .
N2 N 0.3546(3) 0.72212(19) 0.8688(2) 0.0175(8) Uani 1.000000 .
C2 C 0.4070(3) 0.7063(3) 0.3464(3) 0.0161(9) Uani 1.000000 .
C7 C 0.3604(4) 0.6114(2) 0.7845(3) 0.0165(10) Uani 1.000000 .
C3 C 0.4089(3) 0.7202(2) 0.2562(3) 0.0172(8) Uani 1.000000 .
C17 C 0.3384(3) 0.7329(2) 0.7126(3) 0.0180(9) Uani 1.000000 .
H17 H 0.3361(3) 0.7096(2) 0.6571(3) 0.0216(10) Uiso 1.000000 R
C1 C 0.4039(3) 0.6360(3) 0.3765(3) 0.0158(8) Uani 1.000000 .
C4 C 0.4064(3) 0.6655(3) 0.1951(3) 0.0165(8) Uani 1.000000 .
C6 C 0.4009(3) 0.5806(3) 0.3150(3) 0.0182(9) Uani 1.000000 .
C15 C 0.3311(3) 0.8383(3) 0.8004(3) 0.0224(10) Uani 1.000000 .
H15 H 0.3239(3) 0.8890(3) 0.8074(3) 0.0268(12) Uiso 1.000000 R
C13 C 0.3520(3) 0.6913(2) 0.7889(3) 0.0153(9) Uani 1.000000 .
C16 C 0.3284(3) 0.8073(2) 0.7172(3) 0.0187(9) Uani 1.000000 .
C18 C 0.3111(4) 0.8520(2) 0.6356(3) 0.0259(10) Uani 1.000000 .
H18a H 0.341(2) 0.8275(9) 0.5850(4) 0.0389(15) Uiso 1.000000 GR
H18b H 0.2379(4) 0.8578(14) 0.6259(12) 0.0389(15) Uiso 1.000000 GR
H18c H 0.343(2) 0.8996(7) 0.6430(9) 0.0389(15) Uiso 1.000000 GR
C9 C 0.3738(3) 0.4643(2) 0.7745(3) 0.0240(10) Uani 1.000000 .
H9 H 0.3797(3) 0.4134(2) 0.7684(3) 0.0288(12) Uiso 1.000000 R
C11 C 0.3564(3) 0.5706(3) 0.8600(3) 0.0185(9) Uani 1.000000 .
H11 H 0.3490(3) 0.5940(3) 0.9151(3) 0.0222(11) Uiso 1.000000 R
C8 C 0.3757(4) 0.5091(3) 0.7010(3) 0.0227(10) Uani 1.000000 .
H8 H 0.3813(4) 0.4868(3) 0.6450(3) 0.0273(12) Uiso 1.000000 R
C14 C 0.3445(3) 0.7940(2) 0.8729(3) 0.0214(10) Uani 1.000000 .
H14 H 0.3466(3) 0.8162(2) 0.9291(3) 0.0256(11) Uiso 1.000000 R
C5 C 0.4021(3) 0.5952(3) 0.2266(4) 0.0185(9) Uani 1.000000 .
C10 C 0.3632(3) 0.4956(2) 0.8566(3) 0.0194(9) Uani 1.000000 .
C12 C 0.3594(4) 0.4504(3) 0.9393(3) 0.0318(11) Uani 1.000000 .
H12a H 0.2886(4) 0.4444(15) 0.9579(13) 0.0477(17) Uiso 1.000000 GR
H12b H 0.389(2) 0.4028(7) 0.9278(7) 0.0477(17) Uiso 1.000000 GR
H12c H 0.398(2) 0.4746(9) 0.9859(7) 0.0477(17) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.095(4) . ?
I2 C4 2.079(4) . ?
F4 C6 1.354(5) . ?
F1 C2 1.334(5) . ?
F2 C3 1.341(5) . ?
F3 C5 1.355(6) . ?
N1 C7 1.359(7) . ?
N1 C8 1.332(6) . ?
N2 C13 1.345(6) . ?
N2 C14 1.339(6) . ?
C2 C3 1.399(7) . ?
C2 C1 1.380(7) . ?
C7 C13 1.484(5) . ?
C7 C11 1.378(7) . ?
C3 C4 1.374(6) . ?
C17 H17 0.9500 . ?
C17 C13 1.404(6) . ?
C17 C16 1.386(6) . ?
C1 C6 1.389(6) . ?
C4 C5 1.388(7) . ?
C6 C5 1.375(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(6) . ?
C15 C14 1.386(6) . ?
C16 C18 1.510(6) . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C9 H9 0.9500 . ?
C9 C8 1.393(7) . ?
C9 C10 1.385(7) . ?
C11 H11 0.9500 . ?
C11 C10 1.392(6) . ?
C8 H8 0.9500 . ?
C14 H14 0.9500 . ?
C10 C12 1.514(6) . ?
C12 H12a 0.9800 . ?
C12 H12b 0.9800 . ?
C12 H12c 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C7 116.6(4) . . ?
C14 N2 C13 117.5(4) . . ?
C3 C2 F1 118.9(4) . . ?
C1 C2 F1 121.1(4) . . ?
C1 C2 C3 120.0(4) . . ?
C13 C7 N1 117.5(4) . . ?
C11 C7 N1 122.2(4) . . ?
C11 C7 C13 120.4(4) . . ?
C2 C3 F2 117.6(4) . . ?
C4 C3 F2 120.4(4) . . ?
C4 C3 C2 122.0(4) . . ?
C13 C17 H17 119.5(3) . . ?
C16 C17 H17 119.5(3) . . ?
C16 C17 C13 121.0(4) . . ?
C2 C1 I1 120.3(3) . . ?
C6 C1 I1 121.5(3) . . ?
C6 C1 C2 118.2(4) . . ?
C3 C4 I2 121.5(3) . . ?
C5 C4 I2 121.2(3) . . ?
C5 C4 C3 117.2(4) . . ?
C1 C6 F4 119.9(4) . . ?
C5 C6 F4 118.9(4) . . ?
C5 C6 C1 121.1(5) . . ?
C16 C15 H15 120.4(3) . . ?
C14 C15 H15 120.4(3) . . ?
C14 C15 C16 119.1(4) . . ?
C7 C13 N2 117.5(3) . . ?
C17 C13 N2 121.4(4) . . ?
C17 C13 C7 121.1(4) . . ?
C15 C16 C17 116.9(4) . . ?
C18 C16 C17 121.1(4) . . ?
C18 C16 C15 121.9(4) . . ?
H18a C18 C16 109.5 . . ?
H18b C18 C16 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C16 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
C8 C9 H9 120.7(3) . . ?
C10 C9 H9 120.7(3) . . ?
C10 C9 C8 118.7(4) . . ?
H11 C11 C7 119.6(3) . . ?
C10 C11 C7 120.9(4) . . ?
C10 C11 H11 119.6(3) . . ?
C9 C8 N1 124.5(5) . . ?
H8 C8 N1 117.7(3) . . ?
H8 C8 C9 117.7(3) . . ?
C15 C14 N2 124.2(4) . . ?
H14 C14 N2 117.9(2) . . ?
H14 C14 C15 117.9(3) . . ?
C4 C5 F3 120.4(5) . . ?
C6 C5 F3 118.2(5) . . ?
C6 C5 C4 121.5(5) . . ?
C11 C10 C9 117.2(4) . . ?
C12 C10 C9 121.7(4) . . ?
C12 C10 C11 121.2(4) . . ?
H12a C12 C10 109.5 . . ?
H12b C12 C10 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C10 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 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
I1 C1 C2 F1 0.6(4) . . . . ?
I1 C1 C2 C3 -179.7(3) . . . . ?
I1 C1 C6 F4 0.6(4) . . . . ?
I1 C1 C6 C5 179.2(3) . . . . ?
I2 C4 C3 F2 -3.3(4) . . . . ?
I2 C4 C3 C2 176.7(3) . . . . ?
I2 C4 C5 F3 1.6(4) . . . . ?
I2 C4 C5 C6 -177.2(3) . . . . ?
F4 C6 C1 C2 -177.9(4) . . . . ?
F4 C6 C5 F3 -0.2(4) . . . . ?
F4 C6 C5 C4 178.7(4) . . . . ?
F1 C2 C3 F2 0.6(5) . . . . ?
F1 C2 C3 C4 -179.4(4) . . . . ?
F1 C2 C1 C6 179.1(4) . . . . ?
F2 C3 C2 C1 -179.1(3) . . . . ?
F2 C3 C4 C5 179.9(4) . . . . ?
F3 C5 C4 C3 178.5(4) . . . . ?
F3 C5 C6 C1 -178.8(4) . . . . ?
N1 C7 C13 N2 -172.1(5) . . . . ?
N1 C7 C13 C17 10.0(5) . . . . ?
N1 C7 C11 C10 0.4(5) . . . . ?
N1 C8 C9 C10 1.6(6) . . . . ?
N2 C13 C7 C11 8.9(5) . . . . ?
N2 C13 C17 C16 0.8(5) . . . . ?
N2 C14 C15 C16 -0.4(5) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C2 C1 C6 C5 0.6(5) . . . . ?
C7 C13 C17 C16 178.6(5) . . . . ?
C7 C11 C10 C9 -0.1(5) . . . . ?
C7 C11 C10 C12 179.7(4) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C17 C16 C15 C14 0.7(4) . . . . ?
C1 C6 C5 C4 0.1(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_3Br2F8bph_2DABCO
_database_code_depnum_ccdc_archive 'CCDC 2092672'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         '3(Br2 C12 F8), 1.5(C6 H12 N2)'
_chemical_formula_sum            'C45 H18 Br6 F24 N3'
_chemical_formula_weight         1536.047
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.938(3)
_cell_length_b                   10.577(4)
_cell_length_c                   29.826(11)
_cell_angle_alpha                91.873(11)
_cell_angle_beta                 94.086(13)
_cell_angle_gamma                105.304(11)
_cell_volume                     2405.8(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.725
_cell_measurement_theta_min      2.486
_exptl_absorpt_coefficient_mu    5.139
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0749 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.8066.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.120
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1468.720
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.049
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            69289
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.9994
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.08
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              38
_reflns_limit_l_min              0
_reflns_number_gt                9123
_reflns_number_total             11063
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.0381
_refine_diff_density_min         -1.0778
_refine_diff_density_rms         0.1278
_refine_ls_d_res_high            0.7697
_refine_ls_d_res_low             9.7984
_refine_ls_goodness_of_fit_ref   1.0693
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     739
_refine_ls_number_reflns         11063
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.0675
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+3.7078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0620
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
N4 \\sim C44 \\sim C46 \\sim C48: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.1 within 2A
N3 \\sim C43 \\sim C45 \\sim C47: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.1 within 2A
2. Others
 Fixed Sof: N3(0.5) N4(0.5) C43(0.5) H43a(0.5) H43b(0.5) C44(0.5) H44a(0.5)
 H44b(0.5) C45(0.5) H45a(0.5) H45b(0.5) C46(0.5) H46a(0.5) H46b(0.5) C47(0.5)
 H47a(0.5) H47b(0.5) C48(0.5) H48a(0.5) H48b(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C37(H37a,H37b), C38(H38a,H38b), C39(H39a,H39b), C40(H40a,H40b), C41(H41a,
 H41b), C42(H42a,H42b), C43(H43a,H43b), C44(H44a,H44b), C45(H45a,H45b),
 C46(H46a,H46b), C47(H47a,H47b), C48(H48a,H48b)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
Br1 Br 0.11023(3) -0.17132(3) 0.115360(9) 0.01836(6) Uani 1.000000 . . .
Br2 Br 1.33074(4) 0.20838(3) 0.325581(10) 0.02739(7) Uani 1.000000 . . .
F1 F 0.3729(2) 0.09921(15) 0.12026(5) 0.0219(3) Uani 1.000000 . . .
F2 F 0.6623(2) 0.19527(15) 0.17474(5) 0.0213(3) Uani 1.000000 . . .
F3 F 0.5798(2) -0.21483(15) 0.24114(5) 0.0209(3) Uani 1.000000 . . .
F4 F 0.2829(2) -0.30841(15) 0.18889(5) 0.0222(3) Uani 1.000000 . . .
F5 F 1.0116(2) 0.31663(16) 0.31741(6) 0.0259(4) Uani 1.000000 . . .
F6 F 0.7053(2) 0.22169(15) 0.26841(6) 0.0239(4) Uani 1.000000 . . .
F7 F 0.9108(2) -0.12605(15) 0.21025(5) 0.0232(4) Uani 1.000000 . . .
F8 F 1.2138(2) -0.03392(17) 0.26035(6) 0.0261(4) Uani 1.000000 . . .
C1 C 0.3191(3) -0.1075(3) 0.15295(9) 0.0163(5) Uani 1.000000 . . .
C2 C 0.4208(4) 0.0204(3) 0.15056(9) 0.0167(5) Uani 1.000000 . . .
C3 C 0.5711(4) 0.0699(2) 0.17854(9) 0.0162(5) Uani 1.000000 . . .
C4 C 0.6311(3) -0.0065(2) 0.20960(8) 0.0134(5) Uani 1.000000 . . .
C5 C 0.5295(4) -0.1355(3) 0.21152(9) 0.0170(5) Uani 1.000000 . . .
C6 C 0.3766(4) -0.1847(3) 0.18429(9) 0.0165(5) Uani 1.000000 . . .
C7 C 1.1178(4) 0.1422(3) 0.29063(9) 0.0180(5) Uani 1.000000 . . .
C8 C 0.9870(4) 0.2065(3) 0.29145(9) 0.0180(5) Uani 1.000000 . . .
C9 C 0.8304(4) 0.1579(3) 0.26585(9) 0.0172(5) Uani 1.000000 . . .
C10 C 0.7984(3) 0.0443(2) 0.23806(8) 0.0150(5) Uani 1.000000 . . .
C11 C 0.9313(4) -0.0176(3) 0.23745(9) 0.0165(5) Uani 1.000000 . . .
C12 C 1.0886(4) 0.0295(3) 0.26314(9) 0.0178(5) Uani 1.000000 . . .
Br3 Br 0.76232(4) 0.23755(3) 0.052908(9) 0.01930(6) Uani 1.000000 . . .
Br6 Br 1.96387(4) 0.59853(3) 0.272201(10) 0.02702(7) Uani 1.000000 . . .
F9 F 0.9102(2) 0.10606(15) 0.13240(6) 0.0224(3) Uani 1.000000 . . .
F10 F 1.2002(2) 0.19837(15) 0.18713(5) 0.0204(3) Uani 1.000000 . . .
F11 F 1.3505(2) 0.57910(14) 0.10426(5) 0.0208(3) Uani 1.000000 . . .
F12 F 1.0553(2) 0.49215(15) 0.05088(5) 0.0225(4) Uani 1.000000 . . .
F13 F 1.5837(2) 0.52705(17) 0.29597(5) 0.0267(4) Uani 1.000000 . . .
F14 F 1.2891(2) 0.43882(16) 0.24207(5) 0.0225(3) Uani 1.000000 . . .
F15 F 1.6220(2) 0.44496(16) 0.11689(5) 0.0235(4) Uani 1.000000 . . .
F16 F 1.9178(2) 0.53228(17) 0.17054(6) 0.0285(4) Uani 1.000000 . . .
C13 C 0.9725(3) 0.2972(3) 0.09026(9) 0.0165(5) Uani 1.000000 . . .
C14 C 1.0152(4) 0.2250(2) 0.12552(9) 0.0171(5) Uani 1.000000 . . .
C15 C 1.1655(4) 0.2726(3) 0.15358(9) 0.0163(5) Uani 1.000000 . . .
C16 C 1.2841(3) 0.3918(3) 0.14768(9) 0.0154(5) Uani 1.000000 . . .
C17 C 1.2411(3) 0.4624(2) 0.11210(9) 0.0161(5) Uani 1.000000 . . .
C18 C 1.0896(4) 0.4177(3) 0.08421(9) 0.0174(5) Uani 1.000000 . . .
C19 C 1.7581(4) 0.5333(3) 0.23454(9) 0.0181(5) Uani 1.000000 . . .
C20 C 1.5959(4) 0.5065(3) 0.25181(9) 0.0173(5) Uani 1.000000 . . .
C21 C 1.4440(4) 0.4608(3) 0.22403(9) 0.0161(5) Uani 1.000000 . . .
C22 C 1.4476(3) 0.4407(2) 0.17777(9) 0.0145(5) Uani 1.000000 . . .
C23 C 1.6109(4) 0.4673(3) 0.16109(9) 0.0173(5) Uani 1.000000 . . .
C24 C 1.7642(4) 0.5121(3) 0.18851(10) 0.0191(6) Uani 1.000000 . . .
Br4 Br 0.46531(5) 0.90085(4) 0.338101(12) 0.03643(9) Uani 1.000000 . . .
Br5 Br 1.20601(4) 0.23379(3) 0.463784(10) 0.02516(7) Uani 1.000000 . . .
F17 F 0.3317(2) 0.63872(18) 0.38157(6) 0.0324(4) Uani 1.000000 . . .
F18 F 0.5122(2) 0.47871(16) 0.41575(6) 0.0261(4) Uani 1.000000 . . .
F19 F 1.0361(2) 0.76207(16) 0.37290(5) 0.0233(4) Uani 1.000000 . . .
F20 F 0.8578(2) 0.92609(17) 0.34168(6) 0.0299(4) Uani 1.000000 . . .
F21 F 1.2642(2) 0.52800(16) 0.48680(5) 0.0247(4) Uani 1.000000 . . .
F22 F 1.0782(2) 0.69040(15) 0.45872(5) 0.0219(3) Uani 1.000000 . . .
F23 F 0.6964(2) 0.34448(16) 0.36735(6) 0.0288(4) Uani 1.000000 . . .
F24 F 0.8752(3) 0.17978(16) 0.39769(6) 0.0340(4) Uani 1.000000 . . .
C25 C 0.5906(4) 0.7860(3) 0.36085(10) 0.0219(6) Uani 1.000000 . . .
C26 C 0.5059(4) 0.6708(3) 0.37963(9) 0.0212(6) Uani 1.000000 . . .
C27 C 0.6000(4) 0.5879(3) 0.39695(9) 0.0195(6) Uani 1.000000 . . .
C28 C 0.7803(4) 0.6151(3) 0.39541(9) 0.0174(5) Uani 1.000000 . . .
C29 C 0.8623(4) 0.7309(3) 0.37642(9) 0.0191(6) Uani 1.000000 . . .
C30 C 0.7701(4) 0.8155(3) 0.35959(9) 0.0210(6) Uani 1.000000 . . .
C31 C 1.0744(4) 0.3492(3) 0.44343(9) 0.0203(6) Uani 1.000000 . . .
C32 C 1.1226(4) 0.4800(3) 0.45760(9) 0.0192(6) Uani 1.000000 . . .
C33 C 1.0272(4) 0.5643(3) 0.44258(9) 0.0184(5) Uani 1.000000 . . .
C34 C 0.8799(4) 0.5231(3) 0.41213(9) 0.0169(5) Uani 1.000000 . . .
C35 C 0.8343(4) 0.3911(3) 0.39793(9) 0.0204(6) Uani 1.000000 . . .
C36 C 0.9277(4) 0.3066(3) 0.41326(10) 0.0232(6) Uani 1.000000 . . .
N1 N -0.1927(3) -0.2188(2) 0.05750(7) 0.0161(5) Uani 1.000000 . . .
N2 N -0.4475(3) -0.1947(2) 0.00274(7) 0.0164(5) Uani 1.000000 . . .
C37 C -0.1293(4) -0.1162(3) 0.02585(9) 0.0188(6) Uani 1.000000 . . .
H37a H -0.0847(4) -0.0301(3) 0.04264(9) 0.0226(7) Uiso 1.000000 R . .
H37b H -0.0315(4) -0.1352(3) 0.01049(9) 0.0226(7) Uiso 1.000000 R . .
C38 C -0.2794(4) -0.1102(3) -0.00968(9) 0.0190(6) Uani 1.000000 . . .
H38a H -0.2542(4) -0.1400(3) -0.03968(9) 0.0228(7) Uiso 1.000000 R . .
H38b H -0.2871(4) -0.0185(3) -0.01134(9) 0.0228(7) Uiso 1.000000 R . .
C39 C -0.2721(4) -0.3434(3) 0.03132(9) 0.0201(6) Uani 1.000000 . . .
H39a H -0.1856(4) -0.3643(3) 0.01204(9) 0.0241(7) Uiso 1.000000 R . .
H39b H -0.3070(4) -0.4153(3) 0.05201(9) 0.0241(7) Uiso 1.000000 R . .
C40 C -0.4359(4) -0.3318(3) 0.00144(10) 0.0204(6) Uani 1.000000 . . .
H40a H -0.5430(4) -0.3893(3) 0.01242(10) 0.0244(7) Uiso 1.000000 R . .
H40b H -0.4278(4) -0.3614(3) -0.02998(10) 0.0244(7) Uiso 1.000000 R . .
C41 C -0.3277(4) -0.1827(3) 0.08267(9) 0.0186(5) Uani 1.000000 . . .
H41a H -0.3796(4) -0.2545(3) 0.10211(9) 0.0223(7) Uiso 1.000000 R . .
H41b H -0.2738(4) -0.1027(3) 0.10221(9) 0.0223(7) Uiso 1.000000 R . .
C42 C -0.4736(4) -0.1573(3) 0.04930(9) 0.0188(6) Uani 1.000000 . . .
H42a H -0.4709(4) -0.0632(3) 0.05159(9) 0.0226(7) Uiso 1.000000 R . .
H42b H -0.5898(4) -0.2090(3) 0.05729(9) 0.0226(7) Uiso 1.000000 R . .
N3 N 1.416(2) 0.0836(15) 0.4881(6) 0.019(2) Uani 0.500000 . U -1
N4 N 1.612(2) -0.0670(15) 0.5086(6) 0.021(2) Uani 0.500000 . U -1
C43 C 1.5736(8) 0.1165(6) 0.4624(2) 0.0234(12) Uani 0.500000 . U -1
H43a H 1.5377(8) 0.1067(6) 0.4297(2) 0.0281(14) Uiso 0.500000 R . -1
H43b H 1.6407(8) 0.2089(6) 0.4698(2) 0.0281(14) Uiso 0.500000 R . -1
C44 C 1.6907(8) 0.0236(6) 0.4744(2) 0.0226(12) Uani 0.500000 . U -1
H44a H 1.8090(8) 0.0763(6) 0.4862(2) 0.0271(14) Uiso 0.500000 R . -1
H44b H 1.7029(8) -0.0274(6) 0.4470(2) 0.0271(14) Uiso 0.500000 R . -1
C45 C 1.4714(8) 0.0998(6) 0.5359(2) 0.0248(12) Uani 0.500000 . U -1
H45a H 1.5354(8) 0.1926(6) 0.5437(2) 0.0298(15) Uiso 0.500000 R . -1
H45b H 1.3671(8) 0.0777(6) 0.5534(2) 0.0298(15) Uiso 0.500000 R . -1
C46 C 1.5920(8) 0.0101(6) 0.54880(19) 0.0236(12) Uani 0.500000 . U -1
H46a H 1.5400(8) -0.0497(6) 0.57200(19) 0.0284(15) Uiso 0.500000 R . -1
H46b H 1.7082(8) 0.0645(6) 0.56145(19) 0.0284(15) Uiso 0.500000 R . -1
C47 C 1.3191(8) -0.0544(5) 0.4768(2) 0.0236(12) Uani 0.500000 . U -1
H47a H 1.2119(8) -0.0772(5) 0.4932(2) 0.0283(15) Uiso 0.500000 R . -1
H47b H 1.2834(8) -0.0667(5) 0.4441(2) 0.0283(15) Uiso 0.500000 R . -1
C48 C 1.4375(8) -0.1460(5) 0.4901(2) 0.0251(13) Uani 0.500000 . U -1
H48a H 1.4493(8) -0.1996(5) 0.4632(2) 0.0301(15) Uiso 0.500000 R . -1
H48b H 1.3825(8) -0.2063(5) 0.5128(2) 0.0301(15) Uiso 0.500000 R . -1


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 1.886(3) . ?
Br2 C7 1.874(3) . ?
F1 C2 1.350(3) . ?
F2 C3 1.345(3) . ?
F3 C5 1.349(3) . ?
F4 C6 1.340(3) . ?
F5 C8 1.340(3) . ?
F6 C9 1.345(3) . ?
F7 C11 1.350(3) . ?
F8 C12 1.343(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.392(4) . ?
C2 C3 1.376(4) . ?
C3 C4 1.389(3) . ?
C4 C5 1.395(4) . ?
C4 C10 1.485(3) . ?
C5 C6 1.379(4) . ?
C7 C8 1.384(4) . ?
C7 C12 1.382(4) . ?
C8 C9 1.377(4) . ?
C9 C10 1.392(4) . ?
C10 C11 1.380(4) . ?
C11 C12 1.381(4) . ?
Br3 C13 1.886(3) . ?
Br6 C19 1.870(3) . ?
F9 C14 1.345(3) . ?
F10 C15 1.349(3) . ?
F11 C17 1.347(3) . ?
F12 C18 1.345(3) . ?
F13 C20 1.342(3) . ?
F14 C21 1.345(3) . ?
F15 C23 1.345(3) . ?
F16 C24 1.336(3) . ?
C13 C14 1.394(4) . ?
C13 C18 1.390(4) . ?
C14 C15 1.375(4) . ?
C15 C16 1.385(4) . ?
C16 C17 1.391(4) . ?
C16 C22 1.485(4) . ?
C17 C18 1.376(4) . ?
C19 C20 1.384(4) . ?
C19 C24 1.390(4) . ?
C20 C21 1.378(4) . ?
C21 C22 1.392(4) . ?
C22 C23 1.385(4) . ?
C23 C24 1.379(4) . ?
Br4 C25 1.876(3) . ?
Br5 C31 1.893(3) . ?
F17 C26 1.340(3) . ?
F18 C27 1.344(3) . ?
F19 C29 1.344(3) . ?
F20 C30 1.343(3) . ?
F21 C32 1.346(3) . ?
F22 C33 1.349(3) . ?
F23 C35 1.348(3) . ?
F24 C36 1.351(3) . ?
C25 C26 1.384(4) . ?
C25 C30 1.380(4) . ?
C26 C27 1.384(4) . ?
C27 C28 1.388(4) . ?
C28 C29 1.386(4) . ?
C28 C34 1.484(4) . ?
C29 C30 1.382(4) . ?
C31 C32 1.378(4) . ?
C31 C36 1.384(4) . ?
C32 C33 1.379(4) . ?
C33 C34 1.392(4) . ?
C34 C35 1.391(4) . ?
C35 C36 1.373(4) . ?
N1 C37 1.473(3) . ?
N1 C39 1.472(3) . ?
N1 C41 1.473(3) . ?
N2 C38 1.476(3) . ?
N2 C40 1.477(3) . ?
N2 C42 1.475(3) . ?
C37 H37a 0.9900 . ?
C37 H37b 0.9900 . ?
C37 C38 1.553(4) . ?
C38 H38a 0.9900 . ?
C38 H38b 0.9900 . ?
C39 H39a 0.9900 . ?
C39 H39b 0.9900 . ?
C39 C40 1.557(4) . ?
C40 H40a 0.9900 . ?
C40 H40b 0.9900 . ?
C41 H41a 0.9900 . ?
C41 H41b 0.9900 . ?
C41 C42 1.556(4) . ?
C42 H42a 0.9900 . ?
C42 H42b 0.9900 . ?
N3 C43 1.483(15) . ?
N3 C45 1.452(19) . ?
N3 C47 1.475(15) . ?
N4 C44 1.478(14) . ?
N4 C46 1.471(18) . ?
N4 C48 1.475(17) . ?
C43 H43a 0.9900 . ?
C43 H43b 0.9900 . ?
C43 C44 1.554(8) . ?
C44 H44a 0.9900 . ?
C44 H44b 0.9900 . ?
C45 H45a 0.9900 . ?
C45 H45b 0.9900 . ?
C45 C46 1.554(8) . ?
C46 H46a 0.9900 . ?
C46 H46b 0.9900 . ?
C47 H47a 0.9900 . ?
C47 H47b 0.9900 . ?
C47 C48 1.559(8) . ?
C48 H48a 0.9900 . ?
C48 H48b 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
C2 C1 Br1 120.62(19) . . ?
C6 C1 Br1 122.0(2) . . ?
C6 C1 C2 117.3(2) . . ?
C1 C2 F1 119.9(2) . . ?
C3 C2 F1 118.6(2) . . ?
C3 C2 C1 121.5(2) . . ?
C2 C3 F2 118.3(2) . . ?
C4 C3 F2 119.9(2) . . ?
C4 C3 C2 121.8(2) . . ?
C5 C4 C3 116.5(2) . . ?
C10 C4 C3 121.9(2) . . ?
C10 C4 C5 121.5(2) . . ?
C4 C5 F3 119.5(2) . . ?
C6 C5 F3 118.4(2) . . ?
C6 C5 C4 122.0(2) . . ?
C1 C6 F4 120.4(2) . . ?
C5 C6 F4 118.7(2) . . ?
C5 C6 C1 120.9(2) . . ?
C8 C7 Br2 120.5(2) . . ?
C12 C7 Br2 120.9(2) . . ?
C12 C7 C8 118.6(2) . . ?
C7 C8 F5 120.1(2) . . ?
C9 C8 F5 119.3(2) . . ?
C9 C8 C7 120.5(2) . . ?
C8 C9 F6 118.6(2) . . ?
C10 C9 F6 119.7(2) . . ?
C10 C9 C8 121.7(2) . . ?
C9 C10 C4 121.7(2) . . ?
C11 C10 C4 121.4(2) . . ?
C11 C10 C9 116.8(2) . . ?
C10 C11 F7 119.9(2) . . ?
C12 C11 F7 117.9(2) . . ?
C12 C11 C10 122.2(2) . . ?
C7 C12 F8 120.6(2) . . ?
C11 C12 F8 119.3(2) . . ?
C11 C12 C7 120.1(2) . . ?
C14 C13 Br3 121.9(2) . . ?
C18 C13 Br3 120.8(2) . . ?
C18 C13 C14 117.3(2) . . ?
C13 C14 F9 120.3(2) . . ?
C15 C14 F9 118.6(2) . . ?
C15 C14 C13 121.1(2) . . ?
C14 C15 F10 118.5(2) . . ?
C16 C15 F10 119.2(2) . . ?
C16 C15 C14 122.2(2) . . ?
C17 C16 C15 116.2(2) . . ?
C22 C16 C15 121.6(2) . . ?
C22 C16 C17 122.2(2) . . ?
C16 C17 F11 119.5(2) . . ?
C18 C17 F11 118.1(2) . . ?
C18 C17 C16 122.5(2) . . ?
C13 C18 F12 120.0(2) . . ?
C17 C18 F12 119.2(2) . . ?
C17 C18 C13 120.8(2) . . ?
C20 C19 Br6 120.7(2) . . ?
C24 C19 Br6 120.9(2) . . ?
C24 C19 C20 118.4(2) . . ?
C19 C20 F13 120.4(2) . . ?
C21 C20 F13 118.7(2) . . ?
C21 C20 C19 120.8(2) . . ?
C20 C21 F14 118.9(2) . . ?
C22 C21 F14 119.6(2) . . ?
C22 C21 C20 121.6(2) . . ?
C21 C22 C16 121.7(2) . . ?
C23 C22 C16 121.4(2) . . ?
C23 C22 C21 116.9(2) . . ?
C22 C23 F15 119.3(2) . . ?
C24 C23 F15 118.4(2) . . ?
C24 C23 C22 122.3(2) . . ?
C19 C24 F16 120.5(2) . . ?
C23 C24 F16 119.4(2) . . ?
C23 C24 C19 120.1(3) . . ?
C26 C25 Br4 121.0(2) . . ?
C30 C25 Br4 120.5(2) . . ?
C30 C25 C26 118.5(2) . . ?
C25 C26 F17 120.4(2) . . ?
C27 C26 F17 119.1(3) . . ?
C27 C26 C25 120.5(3) . . ?
C26 C27 F18 118.2(2) . . ?
C28 C27 F18 120.0(2) . . ?
C28 C27 C26 121.8(3) . . ?
C29 C28 C27 116.7(2) . . ?
C34 C28 C27 121.7(2) . . ?
C34 C28 C29 121.6(2) . . ?
C28 C29 F19 119.9(2) . . ?
C30 C29 F19 118.0(2) . . ?
C30 C29 C28 122.0(3) . . ?
C25 C30 F20 120.6(2) . . ?
C29 C30 F20 119.0(3) . . ?
C29 C30 C25 120.5(3) . . ?
C32 C31 Br5 121.2(2) . . ?
C36 C31 Br5 121.6(2) . . ?
C36 C31 C32 117.2(2) . . ?
C31 C32 F21 120.3(2) . . ?
C33 C32 F21 118.6(2) . . ?
C33 C32 C31 121.2(3) . . ?
C32 C33 F22 118.3(2) . . ?
C34 C33 F22 119.3(2) . . ?
C34 C33 C32 122.3(2) . . ?
C33 C34 C28 122.0(2) . . ?
C35 C34 C28 122.4(2) . . ?
C35 C34 C33 115.6(2) . . ?
C34 C35 F23 119.2(2) . . ?
C36 C35 F23 118.6(2) . . ?
C36 C35 C34 122.2(3) . . ?
C31 C36 F24 120.0(2) . . ?
C35 C36 F24 118.5(3) . . ?
C35 C36 C31 121.5(3) . . ?
C39 N1 C37 108.3(2) . . ?
C41 N1 C37 108.6(2) . . ?
C41 N1 C39 109.0(2) . . ?
C40 N2 C38 108.2(2) . . ?
C42 N2 C38 108.8(2) . . ?
C42 N2 C40 108.2(2) . . ?
H37a C37 N1 109.55(14) . . ?
H37b C37 N1 109.55(14) . . ?
H37b C37 H37a 108.1 . . ?
C38 C37 N1 110.5(2) . . ?
C38 C37 H37a 109.55(15) . . ?
C38 C37 H37b 109.55(15) . . ?
C37 C38 N2 109.9(2) . . ?
H38a C38 N2 109.68(14) . . ?
H38a C38 C37 109.68(15) . . ?
H38b C38 N2 109.68(14) . . ?
H38b C38 C37 109.68(15) . . ?
H38b C38 H38a 108.2 . . ?
H39a C39 N1 109.71(15) . . ?
H39b C39 N1 109.71(14) . . ?
H39b C39 H39a 108.2 . . ?
C40 C39 N1 109.8(2) . . ?
C40 C39 H39a 109.71(15) . . ?
C40 C39 H39b 109.71(15) . . ?
C39 C40 N2 110.4(2) . . ?
H40a C40 N2 109.57(14) . . ?
H40a C40 C39 109.57(15) . . ?
H40b C40 N2 109.57(14) . . ?
H40b C40 C39 109.57(15) . . ?
H40b C40 H40a 108.1 . . ?
H41a C41 N1 109.68(14) . . ?
H41b C41 N1 109.68(13) . . ?
H41b C41 H41a 108.2 . . ?
C42 C41 N1 109.9(2) . . ?
C42 C41 H41a 109.68(14) . . ?
C42 C41 H41b 109.68(14) . . ?
C41 C42 N2 110.4(2) . . ?
H42a C42 N2 109.58(14) . . ?
H42a C42 C41 109.58(14) . . ?
H42b C42 N2 109.58(14) . . ?
H42b C42 C41 109.58(14) . . ?
H42b C42 H42a 108.1 . . ?
C45 N3 C43 108.9(12) . . ?
C47 N3 C43 108.8(11) . . ?
C47 N3 C45 109.2(10) . . ?
C46 N4 C44 109.0(10) . . ?
C48 N4 C44 108.8(12) . . ?
C48 N4 C46 108.8(11) . . ?
H43a C43 N3 109.8(8) . . ?
H43b C43 N3 109.8(7) . . ?
H43b C43 H43a 108.2 . . ?
C44 C43 N3 109.6(8) . . ?
C44 C43 H43a 109.8(3) . . ?
C44 C43 H43b 109.8(3) . . ?
C43 C44 N4 110.3(9) . . ?
H44a C44 N4 109.6(8) . . ?
H44a C44 C43 109.6(3) . . ?
H44b C44 N4 109.6(7) . . ?
H44b C44 C43 109.6(3) . . ?
H44b C44 H44a 108.1 . . ?
H45a C45 N3 109.5(6) . . ?
H45b C45 N3 109.5(6) . . ?
H45b C45 H45a 108.0 . . ?
C46 C45 N3 110.9(8) . . ?
C46 C45 H45a 109.5(3) . . ?
C46 C45 H45b 109.5(3) . . ?
C45 C46 N4 109.5(9) . . ?
H46a C46 N4 109.8(6) . . ?
H46a C46 C45 109.8(3) . . ?
H46b C46 N4 109.8(7) . . ?
H46b C46 C45 109.8(3) . . ?
H46b C46 H46a 108.2 . . ?
H47a C47 N3 109.7(6) . . ?
H47b C47 N3 109.7(7) . . ?
H47b C47 H47a 108.2 . . ?
C48 C47 N3 109.7(9) . . ?
C48 C47 H47a 109.7(3) . . ?
C48 C47 H47b 109.7(3) . . ?
C47 C48 N4 110.1(8) . . ?
H48a C48 N4 109.6(7) . . ?
H48a C48 C47 109.6(3) . . ?
H48b C48 N4 109.6(7) . . ?
H48b C48 C47 109.6(3) . . ?
H48b C48 H48a 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 F1 -1.8(2) . . . . ?
Br1 C1 C2 C3 178.2(2) . . . . ?
Br1 C1 C6 F4 -0.5(2) . . . . ?
Br1 C1 C6 C5 -179.7(2) . . . . ?
Br2 C7 C8 F5 -0.2(2) . . . . ?
Br2 C7 C8 C9 -179.9(2) . . . . ?
Br2 C7 C12 F8 -1.1(2) . . . . ?
Br2 C7 C12 C11 -179.7(2) . . . . ?
F1 C2 C1 C6 178.9(2) . . . . ?
F1 C2 C3 F2 0.8(3) . . . . ?
F1 C2 C3 C4 -178.1(2) . . . . ?
F2 C3 C2 C1 -179.2(2) . . . . ?
F2 C3 C4 C5 -180.0(2) . . . . ?
F2 C3 C4 C10 -2.4(3) . . . . ?
F3 C5 C4 C3 -179.6(2) . . . . ?
F3 C5 C4 C10 2.7(3) . . . . ?
F3 C5 C6 F4 1.1(3) . . . . ?
F3 C5 C6 C1 -179.6(2) . . . . ?
F4 C6 C1 C2 178.8(2) . . . . ?
F4 C6 C5 C4 -178.1(2) . . . . ?
F5 C8 C7 C12 -179.4(2) . . . . ?
F5 C8 C9 F6 -1.2(3) . . . . ?
F5 C8 C9 C10 179.5(2) . . . . ?
F6 C9 C8 C7 178.5(2) . . . . ?
F6 C9 C10 C4 2.2(3) . . . . ?
F6 C9 C10 C11 -179.1(2) . . . . ?
F7 C11 C10 C4 0.5(3) . . . . ?
F7 C11 C10 C9 -178.1(2) . . . . ?
F7 C11 C12 F8 -0.3(3) . . . . ?
F7 C11 C12 C7 178.3(2) . . . . ?
F8 C12 C7 C8 178.1(2) . . . . ?
F8 C12 C11 C10 -178.7(2) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
C1 C6 C5 C4 1.2(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C2 C3 C4 C10 176.5(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C3 C4 C10 C9 56.2(3) . . . . ?
C3 C4 C10 C11 -122.3(3) . . . . ?
C4 C10 C9 C8 -178.5(3) . . . . ?
C4 C10 C11 C12 179.0(2) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C12 C11 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
Br3 C13 C14 F9 3.5(2) . . . . ?
Br3 C13 C14 C15 -177.2(2) . . . . ?
Br3 C13 C18 F12 -1.2(2) . . . . ?
Br3 C13 C18 C17 178.6(2) . . . . ?
Br6 C19 C20 F13 0.1(2) . . . . ?
Br6 C19 C20 C21 178.8(2) . . . . ?
Br6 C19 C24 F16 3.0(2) . . . . ?
Br6 C19 C24 C23 -178.2(2) . . . . ?
F9 C14 C13 C18 -178.0(2) . . . . ?
F9 C14 C15 F10 -0.7(3) . . . . ?
F9 C14 C15 C16 177.4(2) . . . . ?
F10 C15 C14 C13 -180.0(2) . . . . ?
F10 C15 C16 C17 179.2(2) . . . . ?
F10 C15 C16 C22 -0.8(3) . . . . ?
F11 C17 C16 C15 -179.8(2) . . . . ?
F11 C17 C16 C22 0.1(3) . . . . ?
F11 C17 C18 F12 -1.0(3) . . . . ?
F11 C17 C18 C13 179.2(2) . . . . ?
F12 C18 C13 C14 -179.7(2) . . . . ?
F12 C18 C17 C16 179.0(2) . . . . ?
F13 C20 C19 C24 -179.2(2) . . . . ?
F13 C20 C21 F14 0.2(3) . . . . ?
F13 C20 C21 C22 178.3(2) . . . . ?
F14 C21 C20 C19 -178.5(2) . . . . ?
F14 C21 C22 C16 -1.8(3) . . . . ?
F14 C21 C22 C23 178.9(2) . . . . ?
F15 C23 C22 C16 -1.8(3) . . . . ?
F15 C23 C22 C21 177.5(2) . . . . ?
F15 C23 C24 F16 0.3(3) . . . . ?
F15 C23 C24 C19 -178.5(2) . . . . ?
F16 C24 C19 C20 -177.7(2) . . . . ?
F16 C24 C23 C22 178.1(2) . . . . ?
C13 C14 C15 C16 -1.9(3) . . . . ?
C13 C18 C17 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C14 C15 C16 C22 -178.8(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C15 C16 C22 C21 -58.8(3) . . . . ?
C15 C16 C22 C23 120.6(3) . . . . ?
C16 C22 C21 C20 -179.8(2) . . . . ?
C16 C22 C23 C24 -179.6(2) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C19 C24 C23 C22 -0.7(3) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
Br4 C25 C26 F17 0.5(3) . . . . ?
Br4 C25 C26 C27 -179.0(2) . . . . ?
Br4 C25 C30 F20 -0.7(3) . . . . ?
Br4 C25 C30 C29 179.9(2) . . . . ?
Br5 C31 C32 F21 -0.7(3) . . . . ?
Br5 C31 C32 C33 179.7(2) . . . . ?
Br5 C31 C36 F24 0.1(3) . . . . ?
Br5 C31 C36 C35 -178.8(2) . . . . ?
F17 C26 C25 C30 179.9(3) . . . . ?
F17 C26 C27 F18 -1.0(3) . . . . ?
F17 C26 C27 C28 179.2(2) . . . . ?
F18 C27 C26 C25 178.5(2) . . . . ?
F18 C27 C28 C29 -178.6(2) . . . . ?
F18 C27 C28 C34 3.0(3) . . . . ?
F19 C29 C28 C27 -178.5(2) . . . . ?
F19 C29 C28 C34 -0.1(3) . . . . ?
F19 C29 C30 F20 -1.8(3) . . . . ?
F19 C29 C30 C25 177.7(2) . . . . ?
F20 C30 C25 C26 180.0(3) . . . . ?
F20 C30 C29 C28 179.9(2) . . . . ?
F21 C32 C31 C36 -179.8(3) . . . . ?
F21 C32 C33 F22 -1.5(3) . . . . ?
F21 C32 C33 C34 179.5(2) . . . . ?
F22 C33 C32 C31 178.1(2) . . . . ?
F22 C33 C34 C28 2.4(3) . . . . ?
F22 C33 C34 C35 -178.7(2) . . . . ?
F23 C35 C34 C28 1.0(3) . . . . ?
F23 C35 C34 C33 -177.9(3) . . . . ?
F23 C35 C36 F24 -1.3(3) . . . . ?
F23 C35 C36 C31 177.6(3) . . . . ?
F24 C36 C31 C32 179.2(3) . . . . ?
F24 C36 C35 C34 -179.8(3) . . . . ?
C25 C26 C27 C28 -1.3(3) . . . . ?
C25 C30 C29 C28 -0.6(3) . . . . ?
C26 C27 C28 C29 1.2(3) . . . . ?
C26 C27 C28 C34 -177.2(3) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C27 C28 C34 C33 -128.7(3) . . . . ?
C27 C28 C34 C35 52.5(3) . . . . ?
C28 C34 C33 C32 -178.7(3) . . . . ?
C28 C34 C35 C36 179.5(3) . . . . ?
C31 C32 C33 C34 -0.9(3) . . . . ?
C31 C36 C35 C34 -0.8(4) . . . . ?
C32 C33 C34 C35 0.3(3) . . . . ?
C33 C34 C35 C36 0.6(3) . . . . ?
N1 C37 C38 N2 8.6(2) . . . . ?
N1 C39 C40 N2 8.7(2) . . . . ?
N1 C41 C42 N2 8.0(2) . . . . ?
N3 C43 C44 N4 -1.4(15) . . . . ?
N3 C45 C46 N4 -0.9(11) . . . . ?
N3 C47 C48 N4 -1.7(13) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
N3 C43 0.0100
N3 C45 0.0100
N3 C47 0.0100
N4 C44 0.0100
N4 C46 0.0100
N4 C48 0.0100

####################################################################### 
# 
# 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_I2F8bph_phenaz
_database_code_depnum_ccdc_archive 'CCDC 2093040'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
loop_
_audit_author_email
apeloqu@clemson.edu
_chemical_formula_moiety         'C12 F8 I2, 2(C6 H4 N)'
_chemical_formula_sum            'C24 H8 F8 I2 N2'
_chemical_formula_weight         730.141
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.7139(6)
_cell_length_b                   12.2385(10)
_cell_length_c                   13.5005(11)
_cell_angle_alpha                113.307(3)
_cell_angle_beta                 99.272(3)
_cell_angle_gamma                94.932(3)
_cell_volume                     1139.37(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9679
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      30.064
_cell_measurement_theta_min      2.712
_exptl_absorpt_coefficient_mu    2.842
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0626 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.9248.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.128
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             686.890
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.125
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.9976
_diffrn_reflns_Laue_measured_fraction_max 0.9979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33909
_diffrn_reflns_point_group_measured_fraction_full 0.9976
_diffrn_reflns_point_group_measured_fraction_max 0.9979
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.71
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9979
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine focus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              -15
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4343
_reflns_number_total             4656
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.3912
_refine_diff_density_min         -0.3641
_refine_diff_density_rms         0.0710
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             7.5085
_refine_ls_goodness_of_fit_ref   1.0633
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4656
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0163
_refine_ls_R_factor_gt           0.0143
_refine_ls_restrained_S_all      1.0633
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0110P)²+1.0645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0340
_refine_ls_wR_factor_ref         0.0355
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
I1 I 0.689356(16) 0.764198(11) 1.183744(10) 0.01766(4) Uani 1.000000 .
I2 I -0.155697(15) 0.211894(11) 0.329172(9) 0.01539(4) Uani 1.000000 .
F1 F 0.76982(14) 0.56544(11) 0.96283(10) 0.0243(3) Uani 1.000000 .
F2 F 0.57517(14) 0.44663(11) 0.75847(9) 0.0215(2) Uani 1.000000 .
F3 F 0.10133(15) 0.65343(11) 0.86570(9) 0.0240(3) Uani 1.000000 .
F4 F 0.29658(16) 0.77527(11) 1.06928(9) 0.0273(3) Uani 1.000000 .
F5 F 0.22279(16) 0.38656(12) 0.40596(9) 0.0268(3) Uani 1.000000 .
F6 F 0.42448(15) 0.52667(11) 0.60492(9) 0.0243(3) Uani 1.000000 .
F7 F -0.00892(14) 0.41265(11) 0.77194(9) 0.0210(2) Uani 1.000000 .
F8 F -0.21323(14) 0.27759(11) 0.57411(9) 0.0217(3) Uani 1.000000 .
C1 C 0.5383(3) 0.67321(17) 1.02274(15) 0.0166(4) Uani 1.000000 .
C2 C 0.6046(2) 0.58950(18) 0.94043(16) 0.0171(4) Uani 1.000000 .
C3 C 0.5043(2) 0.52746(17) 0.83438(15) 0.0159(4) Uani 1.000000 .
C4 C 0.3308(2) 0.54511(17) 0.80573(15) 0.0154(4) Uani 1.000000 .
C5 C 0.2669(3) 0.63023(18) 0.88856(16) 0.0177(4) Uani 1.000000 .
C6 C 0.3679(3) 0.69314(18) 0.99404(16) 0.0187(4) Uani 1.000000 .
C7 C -0.0003(2) 0.32668(17) 0.48429(15) 0.0156(4) Uani 1.000000 .
C8 C 0.1637(3) 0.39214(18) 0.49570(16) 0.0172(4) Uani 1.000000 .
C9 C 0.2684(2) 0.46371(18) 0.59841(16) 0.0173(4) Uani 1.000000 .
C10 C 0.2162(2) 0.47272(17) 0.69486(15) 0.0146(4) Uani 1.000000 .
C11 C 0.0502(2) 0.40872(18) 0.68269(15) 0.0155(4) Uani 1.000000 .
C12 C -0.0554(2) 0.33849(17) 0.57993(16) 0.0154(4) Uani 1.000000 .
N1 N 0.9176(2) 0.89752(15) 1.40223(13) 0.0167(3) Uani 1.000000 .
C13 C 0.8426(2) 0.93450(18) 1.49081(16) 0.0165(4) Uani 1.000000 .
C14 C 1.0743(2) 0.96133(17) 1.40991(16) 0.0158(4) Uani 1.000000 .
C15 C 1.1606(3) 0.92537(19) 1.31905(17) 0.0210(4) Uani 1.000000 .
H15 H 1.1083(3) 0.85587(19) 1.25329(17) 0.0252(5) Uiso 1.000000 R
C16 C 1.3183(3) 0.9906(2) 1.32639(17) 0.0235(4) Uani 1.000000 .
H16 H 1.3749(3) 0.9662(2) 1.26536(17) 0.0282(5) Uiso 1.000000 R
C17 C 1.3992(3) 1.0948(2) 1.42423(17) 0.0243(5) Uani 1.000000 .
H17 H 1.5085(3) 1.1396(2) 1.42738(17) 0.0292(5) Uiso 1.000000 R
C18 C 1.3222(3) 1.13120(19) 1.51316(17) 0.0211(4) Uani 1.000000 .
H18 H 1.3783(3) 1.20054(19) 1.57815(17) 0.0253(5) Uiso 1.000000 R
N2 N -0.3944(2) 0.06020(14) 0.10862(13) 0.0147(3) Uani 1.000000 .
C19 C -0.5562(2) 0.08650(17) 0.08209(15) 0.0144(4) Uani 1.000000 .
C20 C -0.6239(3) 0.17650(18) 0.16409(16) 0.0175(4) Uani 1.000000 .
H20 H -0.5558(3) 0.21650(18) 0.23752(16) 0.0210(5) Uiso 1.000000 R
C21 C -0.7862(3) 0.20511(18) 0.13718(16) 0.0192(4) Uani 1.000000 .
H21 H -0.8300(3) 0.26579(18) 0.19203(16) 0.0230(5) Uiso 1.000000 R
C22 C -0.3371(2) -0.02562(17) 0.02815(15) 0.0137(4) Uani 1.000000 .
C23 C -0.1677(2) -0.05780(18) 0.05210(16) 0.0167(4) Uani 1.000000 .
H23 H -0.0953(2) -0.01795(18) 0.12437(16) 0.0201(5) Uiso 1.000000 R
C24 C -0.1088(3) -0.14535(18) -0.02797(16) 0.0189(4) Uani 1.000000 .
H24 H 0.0040(3) -0.16691(18) -0.01078(16) 0.0226(5) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.0900(18) . ?
I2 C7 2.0904(18) . ?
F1 C2 1.347(2) . ?
F2 C3 1.341(2) . ?
F3 C5 1.346(2) . ?
F4 C6 1.346(2) . ?
F5 C8 1.341(2) . ?
F6 C9 1.343(2) . ?
F7 C11 1.341(2) . ?
F8 C12 1.346(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.379(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.387(3) . ?
C4 C10 1.482(3) . ?
C5 C6 1.378(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.382(3) . ?
C8 C9 1.378(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.392(3) . ?
C11 C12 1.378(3) . ?
N1 C13 1.345(2) . ?
N1 C14 1.348(2) . ?
C13 C14 1.436(3) 2_778 ?
C13 C18 1.426(3) 2_778 ?
C14 C15 1.424(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.363(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.423(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.358(3) . ?
C18 H18 0.9500 . ?
N2 C19 1.344(2) . ?
N2 C22 1.345(2) . ?
C19 C20 1.426(3) . ?
C19 C22 1.439(3) 2_455 ?
C20 H20 0.9500 . ?
C20 C21 1.361(3) . ?
C21 H21 0.9500 . ?
C21 C24 1.423(3) 2_455 ?
C22 C23 1.422(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.360(3) . ?
C24 H24 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
C2 C1 I1 121.36(14) . . ?
C6 C1 I1 121.51(14) . . ?
C6 C1 C2 117.13(17) . . ?
C1 C2 F1 120.23(17) . . ?
C3 C2 F1 118.10(17) . . ?
C3 C2 C1 121.67(17) . . ?
C2 C3 F2 118.93(17) . . ?
C4 C3 F2 119.65(16) . . ?
C4 C3 C2 121.40(17) . . ?
C5 C4 C3 116.32(17) . . ?
C10 C4 C3 122.22(17) . . ?
C10 C4 C5 121.38(17) . . ?
C4 C5 F3 119.32(16) . . ?
C6 C5 F3 118.49(17) . . ?
C6 C5 C4 122.19(18) . . ?
C1 C6 F4 120.30(17) . . ?
C5 C6 F4 118.44(17) . . ?
C5 C6 C1 121.27(18) . . ?
C8 C7 I2 121.63(14) . . ?
C12 C7 I2 121.06(14) . . ?
C12 C7 C8 117.30(17) . . ?
C7 C8 F5 120.12(17) . . ?
C9 C8 F5 118.72(17) . . ?
C9 C8 C7 121.16(17) . . ?
C8 C9 F6 118.80(17) . . ?
C10 C9 F6 119.45(16) . . ?
C10 C9 C8 121.75(17) . . ?
C9 C10 C4 122.37(17) . . ?
C11 C10 C4 120.94(17) . . ?
C11 C10 C9 116.69(17) . . ?
C10 C11 F7 120.11(16) . . ?
C12 C11 F7 118.41(16) . . ?
C12 C11 C10 121.47(17) . . ?
C7 C12 F8 120.00(16) . . ?
C11 C12 F8 118.38(17) . . ?
C11 C12 C7 121.59(17) . . ?
C14 N1 C13 117.67(16) . . ?
C14 C13 N1 121.37(17) 2_778 . ?
C18 C13 N1 119.58(17) 2_778 . ?
C18 C13 C14 119.04(18) 2_778 2_778 ?
C13 C14 N1 120.96(17) 2_778 . ?
C15 C14 N1 120.02(17) . . ?
C15 C14 C13 119.02(17) . 2_778 ?
H15 C15 C14 119.99(11) . . ?
C16 C15 C14 120.03(19) . . ?
C16 C15 H15 119.99(12) . . ?
H16 C16 C15 119.55(12) . . ?
C17 C16 C15 120.90(19) . . ?
C17 C16 H16 119.55(12) . . ?
H17 C17 C16 119.57(12) . . ?
C18 C17 C16 120.85(19) . . ?
C18 C17 H17 119.57(12) . . ?
C17 C18 C13 120.14(19) . 2_778 ?
H18 C18 C13 119.93(11) . 2_778 ?
H18 C18 C17 119.93(12) . . ?
C22 N2 C19 117.27(16) . . ?
C20 C19 N2 119.74(17) . . ?
C22 C19 N2 121.16(17) 2_455 . ?
C22 C19 C20 119.09(17) 2_455 . ?
H20 C20 C19 120.01(11) . . ?
C21 C20 C19 119.99(18) . . ?
C21 C20 H20 120.01(12) . . ?
H21 C21 C20 119.56(12) . . ?
C24 C21 C20 120.88(18) 2_455 . ?
C24 C21 H21 119.56(11) 2_455 . ?
C19 C22 N2 121.56(17) 2_455 . ?
C23 C22 N2 119.55(17) . . ?
C23 C22 C19 118.89(17) . 2_455 ?
H23 C23 C22 119.86(11) . . ?
C24 C23 C22 120.29(18) . . ?
C24 C23 H23 119.86(11) . . ?
C23 C24 C21 120.85(18) . 2_455 ?
H24 C24 C21 119.58(11) . 2_455 ?
H24 C24 C23 119.58(11) . . ?


_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_Br2F8bph_phenaz
_database_code_depnum_ccdc_archive 'CCDC 2093039'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'Br2 C12 F8, 2(C6 H4 N)'
_chemical_formula_sum            'C24 H8 Br2 F8 N2'
_chemical_formula_weight         636.139
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.6092(4)
_cell_length_b                   12.2473(7)
_cell_length_c                   12.8900(8)
_cell_angle_alpha                111.115(2)
_cell_angle_beta                 100.664(2)
_cell_angle_gamma                95.114(2)
_cell_volume                     1085.22(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    101.0
_cell_measurement_theta_max      28.308
_cell_measurement_theta_min      2.764
_exptl_absorpt_coefficient_mu    3.820
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0644 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.8550.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             615.623
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.164
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.9985
_diffrn_reflns_Laue_measured_fraction_max 0.9987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37287
_diffrn_reflns_point_group_measured_fraction_full 0.9985
_diffrn_reflns_point_group_measured_fraction_max 0.9987
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         2.76
_diffrn_ambient_temperature      101.0
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -15
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4181
_reflns_number_total             4612
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.3611
_refine_diff_density_min         -0.3281
_refine_diff_density_rms         0.0685
_refine_ls_d_res_high            0.7900
_refine_ls_d_res_low             7.3690
_refine_ls_goodness_of_fit_ref   1.0713
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4612
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0182
_refine_ls_restrained_S_all      1.0713
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0139P)²+0.9595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0413
_refine_ls_wR_factor_ref         0.0437
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br1 Br -0.19727(2) 0.247183(15) 0.317979(14) 0.01821(5) Uani 1.000000 .
Br2 Br 0.65291(2) 0.776421(15) 1.161774(14) 0.01780(5) Uani 1.000000 .
F1 F 0.18588(16) 0.22499(10) 0.42122(9) 0.0279(3) Uani 1.000000 .
F2 F 0.39231(14) 0.34293(10) 0.63116(9) 0.0244(2) Uani 1.000000 .
F3 F -0.08025(14) 0.55231(9) 0.73600(9) 0.0219(2) Uani 1.000000 .
F4 F -0.28811(14) 0.43414(10) 0.52577(9) 0.0238(2) Uani 1.000000 .
F5 F 0.72382(14) 0.71582(10) 0.92386(9) 0.0224(2) Uani 1.000000 .
F6 F 0.51033(14) 0.58015(10) 0.72058(8) 0.0215(2) Uani 1.000000 .
F7 F 0.07746(14) 0.47249(10) 0.90085(9) 0.0252(2) Uani 1.000000 .
F8 F 0.28630(15) 0.61534(10) 1.10528(9) 0.0267(3) Uani 1.000000 .
C1 C -0.0559(2) 0.32728(15) 0.46766(14) 0.0171(3) Uani 1.000000 .
C2 C 0.1178(3) 0.30594(16) 0.49796(15) 0.0187(4) Uani 1.000000 .
C3 C 0.2246(2) 0.36707(16) 0.60671(15) 0.0179(3) Uani 1.000000 .
C4 C 0.1636(2) 0.45199(15) 0.69043(14) 0.0152(3) Uani 1.000000 .
C5 C -0.0130(2) 0.47090(15) 0.65974(14) 0.0164(3) Uani 1.000000 .
C6 C -0.1207(2) 0.40997(15) 0.55071(15) 0.0166(3) Uani 1.000000 .
C7 C 0.5090(2) 0.67073(15) 1.01924(14) 0.0160(3) Uani 1.000000 .
C8 C 0.5638(2) 0.65715(15) 0.91976(15) 0.0161(3) Uani 1.000000 .
C9 C 0.4535(2) 0.58568(15) 0.81447(14) 0.0157(3) Uani 1.000000 .
C10 C 0.2853(2) 0.52349(15) 0.80403(14) 0.0149(3) Uani 1.000000 .
C11 C 0.2347(2) 0.53445(16) 0.90544(15) 0.0175(3) Uani 1.000000 .
C12 C 0.3431(2) 0.60705(16) 1.01067(14) 0.0181(4) Uani 1.000000 .
N1 N -0.4250(2) 0.10801(13) 0.09463(12) 0.0175(3) Uani 1.000000 .
C13 C -0.5805(2) 0.04204(15) 0.08866(14) 0.0167(3) Uani 1.000000 .
C14 C -0.6727(3) 0.08114(16) 0.17878(15) 0.0207(4) Uani 1.000000 .
H14 H -0.6243(3) 0.15350(16) 0.24262(15) 0.0248(4) Uiso 1.000000 R
C15 C -0.8300(3) 0.01500(17) 0.17351(16) 0.0227(4) Uani 1.000000 .
H15 H -0.8904(3) 0.04163(17) 0.23405(16) 0.0273(5) Uiso 1.000000 R
C16 C -0.3434(2) 0.06751(15) 0.00719(14) 0.0162(3) Uani 1.000000 .
C17 C -0.1782(2) 0.13385(16) 0.00950(15) 0.0202(4) Uani 1.000000 .
H17 H -0.1262(2) 0.20628(16) 0.07250(15) 0.0243(4) Uiso 1.000000 R
C18 C -0.0946(3) 0.09351(17) -0.07858(16) 0.0225(4) Uani 1.000000 .
H18 H 0.0153(3) 0.13838(17) -0.07660(16) 0.0270(5) Uiso 1.000000 R
N2 N 0.8965(2) 0.94084(13) 1.38537(12) 0.0160(3) Uani 1.000000 .
C19 C 0.8341(2) 1.02379(15) 1.46411(14) 0.0151(3) Uani 1.000000 .
C20 C 1.0610(2) 0.91653(15) 1.41975(14) 0.0154(3) Uani 1.000000 .
C21 C 1.1343(2) 0.82990(16) 1.33989(15) 0.0189(4) Uani 1.000000 .
H21 H 1.0675(2) 0.79046(16) 1.26281(15) 0.0226(4) Uiso 1.000000 R
C22 C 1.2996(3) 0.80351(16) 1.37368(15) 0.0206(4) Uani 1.000000 .
H22 H 1.3473(3) 0.74561(16) 1.31977(15) 0.0247(4) Uiso 1.000000 R
C23 C 1.4024(2) 0.86157(16) 1.48904(15) 0.0201(4) Uani 1.000000 .
H23 H 1.5171(2) 0.84129(16) 1.51120(15) 0.0241(4) Uiso 1.000000 R
C24 C 1.3378(2) 0.94549(16) 1.56742(15) 0.0179(3) Uani 1.000000 .
H24 H 1.4080(2) 0.98389(16) 1.64378(15) 0.0215(4) Uiso 1.000000 R


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 1.8767(17) . ?
Br2 C7 1.8814(16) . ?
F1 C2 1.343(2) . ?
F2 C3 1.342(2) . ?
F3 C5 1.3391(19) . ?
F4 C6 1.341(2) . ?
F5 C8 1.3396(19) . ?
F6 C9 1.3402(19) . ?
F7 C11 1.3379(19) . ?
F8 C12 1.341(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.385(2) . ?
C2 C3 1.378(2) . ?
C3 C4 1.388(2) . ?
C4 C5 1.393(2) . ?
C4 C10 1.483(2) . ?
C5 C6 1.383(2) . ?
C7 C8 1.379(2) . ?
C7 C12 1.387(2) . ?
C8 C9 1.380(2) . ?
C9 C10 1.388(2) . ?
C10 C11 1.394(2) . ?
C11 C12 1.377(2) . ?
N1 C13 1.345(2) . ?
N1 C16 1.346(2) . ?
C13 C14 1.425(2) . ?
C13 C16 1.437(2) 2_455 ?
C14 H14 0.9500 . ?
C14 C15 1.360(3) . ?
C15 H15 0.9500 . ?
C15 C18 1.423(3) 2_455 ?
C16 C17 1.424(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.362(3) . ?
C18 H18 0.9500 . ?
N2 C19 1.345(2) . ?
N2 C20 1.344(2) . ?
C19 C20 1.441(2) 2_778 ?
C19 C24 1.421(2) 2_778 ?
C20 C21 1.424(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.359(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.427(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.358(3) . ?
C24 H24 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
C2 C1 Br1 120.63(13) . . ?
C6 C1 Br1 121.44(13) . . ?
C6 C1 C2 117.93(15) . . ?
C1 C2 F1 120.30(15) . . ?
C3 C2 F1 118.70(16) . . ?
C3 C2 C1 121.00(16) . . ?
C2 C3 F2 118.40(15) . . ?
C4 C3 F2 119.67(15) . . ?
C4 C3 C2 121.94(16) . . ?
C5 C4 C3 116.58(15) . . ?
C10 C4 C3 121.11(16) . . ?
C10 C4 C5 122.20(15) . . ?
C4 C5 F3 119.78(15) . . ?
C6 C5 F3 118.46(15) . . ?
C6 C5 C4 121.73(16) . . ?
C1 C6 F4 120.33(15) . . ?
C5 C6 F4 118.85(15) . . ?
C5 C6 C1 120.80(16) . . ?
C8 C7 Br2 120.58(13) . . ?
C12 C7 Br2 121.24(13) . . ?
C12 C7 C8 118.15(15) . . ?
C7 C8 F5 120.29(15) . . ?
C9 C8 F5 118.85(15) . . ?
C9 C8 C7 120.84(16) . . ?
C8 C9 F6 118.19(15) . . ?
C10 C9 F6 119.96(15) . . ?
C10 C9 C8 121.82(15) . . ?
C9 C10 C4 121.42(15) . . ?
C11 C10 C4 121.87(15) . . ?
C11 C10 C9 116.69(15) . . ?
C10 C11 F7 119.37(15) . . ?
C12 C11 F7 118.96(15) . . ?
C12 C11 C10 121.67(16) . . ?
C7 C12 F8 120.20(15) . . ?
C11 C12 F8 119.05(15) . . ?
C11 C12 C7 120.75(16) . . ?
C16 N1 C13 117.43(15) . . ?
C14 C13 N1 119.68(16) . . ?
C16 C13 N1 121.33(16) 2_455 . ?
C16 C13 C14 118.98(16) 2_455 . ?
H14 C14 C13 119.95(10) . . ?
C15 C14 C13 120.10(17) . . ?
C15 C14 H14 119.95(11) . . ?
H15 C15 C14 119.54(11) . . ?
C18 C15 C14 120.92(17) 2_455 . ?
C18 C15 H15 119.54(11) 2_455 . ?
C13 C16 N1 121.24(16) 2_455 . ?
C17 C16 N1 119.65(16) . . ?
C17 C16 C13 119.11(16) . 2_455 ?
H17 C17 C16 119.97(10) . . ?
C18 C17 C16 120.06(16) . . ?
C18 C17 H17 119.97(11) . . ?
C17 C18 C15 120.82(17) . 2_455 ?
H18 C18 C15 119.59(11) . 2_455 ?
H18 C18 C17 119.59(11) . . ?
C20 N2 C19 117.07(15) . . ?
C20 C19 N2 121.31(16) 2_778 . ?
C24 C19 N2 119.70(15) 2_778 . ?
C24 C19 C20 119.00(16) 2_778 2_778 ?
C19 C20 N2 121.63(16) 2_778 . ?
C21 C20 N2 119.49(16) . . ?
C21 C20 C19 118.88(16) . 2_778 ?
H21 C21 C20 119.92(10) . . ?
C22 C21 C20 120.16(16) . . ?
C22 C21 H21 119.92(11) . . ?
H22 C22 C21 119.54(11) . . ?
C23 C22 C21 120.93(17) . . ?
C23 C22 H22 119.54(10) . . ?
H23 C23 C22 119.67(10) . . ?
C24 C23 C22 120.65(17) . . ?
C24 C23 H23 119.67(11) . . ?
C23 C24 C19 120.38(16) . 2_778 ?
H24 C24 C19 119.81(10) . 2_778 ?
H24 C24 C23 119.81(11) . . ?

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 C2 F1 -1.84(16) . . . . ?
Br1 C1 C2 C3 177.95(14) . . . . ?
Br1 C1 C6 F4 0.47(16) . . . . ?
Br1 C1 C6 C5 -178.05(13) . . . . ?
Br2 C7 C8 F5 2.54(16) . . . . ?
Br2 C7 C8 C9 -175.76(13) . . . . ?
Br2 C7 C12 F8 -3.41(16) . . . . ?
Br2 C7 C12 C11 176.72(14) . . . . ?
F1 C2 C1 C6 178.75(16) . . . . ?
F1 C2 C3 F2 -0.00(19) . . . . ?
F1 C2 C3 C4 179.96(16) . . . . ?
F2 C3 C2 C1 -179.80(16) . . . . ?
F2 C3 C4 C5 -178.82(16) . . . . ?
F2 C3 C4 C10 4.8(2) . . . . ?
F3 C5 C4 C3 -179.41(16) . . . . ?
F3 C5 C4 C10 -3.10(19) . . . . ?
F3 C5 C6 F4 -0.38(18) . . . . ?
F3 C5 C6 C1 178.17(15) . . . . ?
F4 C6 C1 C2 179.88(16) . . . . ?
F4 C6 C5 C4 -178.51(15) . . . . ?
F5 C8 C7 C12 -179.28(16) . . . . ?
F5 C8 C9 F6 -1.34(18) . . . . ?
F5 C8 C9 C10 -179.27(15) . . . . ?
F6 C9 C8 C7 176.99(15) . . . . ?
F6 C9 C10 C4 -1.19(19) . . . . ?
F6 C9 C10 C11 -179.40(16) . . . . ?
F7 C11 C10 C4 4.7(2) . . . . ?
F7 C11 C10 C9 -177.12(16) . . . . ?
F7 C11 C12 F8 -1.32(19) . . . . ?
F7 C11 C12 C7 178.56(16) . . . . ?
F8 C12 C7 C8 178.42(16) . . . . ?
F8 C12 C11 C10 179.09(16) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C6 C5 C4 0.0(2) . . . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
C2 C3 C4 C10 -175.14(17) . . . . ?
C3 C4 C5 C6 -1.31(19) . . . . ?
C3 C4 C10 C9 52.63(19) . . . . ?
C3 C4 C10 C11 -129.25(18) . . . . ?
C4 C10 C9 C8 176.71(16) . . . . ?
C4 C10 C11 C12 -175.73(17) . . . . ?
C7 C8 C9 C10 -0.9(2) . . . . ?
C7 C12 C11 C10 -1.0(2) . . . . ?
C8 C9 C10 C11 -1.5(2) . . . . ?
C9 C10 C11 C12 2.5(2) . . . . ?
N1 C13 C14 C15 -179.98(17) . . . . ?
N1 C13 C16 N1 -0.09(17) . . 2_455 2_455 ?
N1 C13 C16 C17 -179.82(17) . . 2_455 2_455 ?
N1 C16 C13 N1 0.09(17) . . 2_455 2_455 ?
N1 C16 C13 C14 -179.76(17) . . 2_455 2_455 ?
N1 C16 C17 C18 179.97(17) . . . . ?
C13 C14 C15 C18 -0.2(2) . . . 2_455 ?
C13 C16 C17 C18 0.2(2) 2_455 . . . ?
C14 C15 C18 C17 -0.0(2) . . 2_455 2_455 ?
C15 C18 C17 C16 -0.2(2) 2_455 . . . ?
N2 C19 C20 N2 0.23(16) . . 2_778 2_778 ?
N2 C19 C20 C21 -179.70(16) . . 2_778 2_778 ?
N2 C19 C24 C23 -179.71(16) . . 2_778 2_778 ?
N2 C20 C19 N2 -0.23(16) . . 2_778 2_778 ?
N2 C20 C19 C24 179.15(16) . . 2_778 . ?
N2 C20 C21 C22 -179.32(16) . . . . ?
C19 C20 C21 C22 0.75(19) 2_778 . . . ?
C19 C24 C23 C22 0.5(2) 2_778 . . . ?
C20 C21 C22 C23 0.0(2) . . . . ?
C21 C22 C23 C24 -0.7(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_I2F8bph_quinox
_database_code_depnum_ccdc_archive 'CCDC 2093038'
loop_
_audit_author_name
_audit_author_address
'Colin D. McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C12 F8 I2, C8 H6 N2'
_chemical_formula_sum            'C20 H6 F8 I2 N2'
_chemical_formula_weight         680.080
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.2738(5)
_cell_length_b                   6.9896(4)
_cell_length_c                   34.5606(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.006(2)
_cell_angle_gamma                90
_cell_volume                     1995.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.634
_cell_measurement_theta_min      2.361
_exptl_absorpt_coefficient_mu    3.235
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0991 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.7974.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.263
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1269.738
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.074
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.9989
_diffrn_reflns_Laue_measured_fraction_max 0.9990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            39071
_diffrn_reflns_point_group_measured_fraction_full 0.9989
_diffrn_reflns_point_group_measured_fraction_max 0.9990
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.36
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9990
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              42
_reflns_limit_l_min              0
_reflns_number_gt                3525
_reflns_number_total             3924
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.4034
_refine_diff_density_min         -0.4400
_refine_diff_density_rms         0.0982
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             8.6283
_refine_ls_goodness_of_fit_ref   1.0613
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0171
_refine_ls_restrained_S_all      1.0613
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0084P)²+2.6899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0361
_refine_ls_wR_factor_ref         0.0388
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19)
;
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_refinement_flags_posn
I1 I 0.369389(19) 0.55105(2) 0.565768(4) 0.01560(5) Uani 1.000000 .
I2 I -0.215301(19) -0.04940(2) 0.289009(4) 0.01520(5) Uani 1.000000 .
F1 F 0.14853(18) 0.74074(19) 0.49840(4) 0.0188(3) Uani 1.000000 .
F2 F 0.02671(17) 0.6117(2) 0.43024(4) 0.0169(3) Uani 1.000000 .
F3 F 0.27693(17) 0.01445(19) 0.45434(4) 0.0168(3) Uani 1.000000 .
F4 F 0.40242(18) 0.1437(2) 0.52232(4) 0.0217(3) Uani 1.000000 .
F5 F -0.20588(17) -0.1676(2) 0.37871(4) 0.0188(3) Uani 1.000000 .
F6 F -0.06029(17) -0.01272(19) 0.44190(4) 0.0154(3) Uani 1.000000 .
F7 F 0.16460(17) 0.4667(2) 0.36491(4) 0.0185(3) Uani 1.000000 .
F8 F 0.00370(17) 0.3273(2) 0.30248(4) 0.0194(3) Uani 1.000000 .
C1 C 0.2805(3) 0.4464(4) 0.51207(7) 0.0141(5) Uani 1.000000 .
C2 C 0.1846(3) 0.5624(3) 0.48763(7) 0.0133(5) Uani 1.000000 .
C3 C 0.1205(3) 0.4944(3) 0.45264(7) 0.0129(5) Uani 1.000000 .
C4 C 0.1444(3) 0.3073(3) 0.44089(7) 0.0123(5) Uani 1.000000 .
C5 C 0.2428(3) 0.1937(3) 0.46521(7) 0.0132(5) Uani 1.000000 .
C6 C 0.3087(3) 0.2613(4) 0.50010(7) 0.0144(5) Uani 1.000000 .
C7 C -0.1032(3) 0.0737(3) 0.33868(7) 0.0138(5) Uani 1.000000 .
C8 C -0.1160(3) -0.0093(3) 0.37476(7) 0.0137(5) Uani 1.000000 .
C9 C -0.0380(3) 0.0680(3) 0.40738(7) 0.0127(5) Uani 1.000000 .
C10 C 0.0600(3) 0.2288(3) 0.40540(7) 0.0126(5) Uani 1.000000 .
C11 C 0.0704(3) 0.3116(3) 0.36916(7) 0.0138(5) Uani 1.000000 .
C12 C -0.0108(3) 0.2374(4) 0.33665(7) 0.0140(5) Uani 1.000000 .
N1 N 0.4589(2) 0.6731(3) 0.64398(6) 0.0163(4) Uani 1.000000 .
N2 N 0.6039(2) 0.6845(3) 0.71959(6) 0.0157(4) Uani 1.000000 .
C13 C 0.4399(3) 0.5355(4) 0.66908(7) 0.0173(5) Uani 1.000000 .
H13 H 0.3749(3) 0.4284(4) 0.66155(7) 0.0208(6) Uiso 1.000000 R
C14 C 0.5129(3) 0.5410(4) 0.70704(7) 0.0165(5) Uani 1.000000 .
H14 H 0.4955(3) 0.4371(4) 0.72406(7) 0.0198(6) Uiso 1.000000 R
C15 C 0.6237(3) 0.8320(3) 0.69428(7) 0.0136(5) Uani 1.000000 .
C16 C 0.7178(3) 0.9932(4) 0.70600(7) 0.0179(5) Uani 1.000000 .
H16 H 0.7668(3) 0.9993(4) 0.73145(7) 0.0214(6) Uiso 1.000000 R
C17 C 0.7379(3) 1.1406(4) 0.68042(8) 0.0203(6) Uani 1.000000 .
H17 H 0.8016(3) 1.2482(4) 0.68824(8) 0.0244(7) Uiso 1.000000 R
C18 C 0.6648(3) 1.1336(4) 0.64259(8) 0.0211(6) Uani 1.000000 .
H18 H 0.6794(3) 1.2370(4) 0.62528(8) 0.0254(7) Uiso 1.000000 R
C19 C 0.5731(3) 0.9797(4) 0.63059(7) 0.0175(5) Uani 1.000000 .
H19 H 0.5246(3) 0.9764(4) 0.60506(7) 0.0210(6) Uiso 1.000000 R
C20 C 0.5508(3) 0.8261(3) 0.65618(7) 0.0138(5) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.092(2) . ?
I2 C7 2.093(2) . ?
F1 C2 1.339(3) . ?
F2 C3 1.346(3) . ?
F3 C5 1.342(3) . ?
F4 C6 1.343(3) . ?
F5 C8 1.345(3) . ?
F6 C9 1.341(3) . ?
F7 C11 1.347(3) . ?
F8 C12 1.348(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.382(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.389(3) . ?
C4 C10 1.484(3) . ?
C5 C6 1.381(3) . ?
C7 C8 1.384(3) . ?
C7 C12 1.380(3) . ?
C8 C9 1.379(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.380(3) . ?
N1 C13 1.310(3) . ?
N1 C20 1.367(3) . ?
N2 C14 1.314(3) . ?
N2 C15 1.368(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.416(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.416(3) . ?
C15 C20 1.420(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.373(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.413(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.368(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.410(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 119.88(18) . . ?
C6 C1 I1 122.40(18) . . ?
C6 C1 C2 117.7(2) . . ?
C1 C2 F1 120.2(2) . . ?
C3 C2 F1 118.9(2) . . ?
C3 C2 C1 120.9(2) . . ?
C2 C3 F2 118.6(2) . . ?
C4 C3 F2 119.5(2) . . ?
C4 C3 C2 121.9(2) . . ?
C5 C4 C3 116.7(2) . . ?
C10 C4 C3 121.5(2) . . ?
C10 C4 C5 121.6(2) . . ?
C4 C5 F3 119.3(2) . . ?
C6 C5 F3 119.0(2) . . ?
C6 C5 C4 121.7(2) . . ?
C1 C6 F4 120.2(2) . . ?
C5 C6 F4 118.7(2) . . ?
C5 C6 C1 121.1(2) . . ?
C8 C7 I2 121.00(18) . . ?
C12 C7 I2 121.47(18) . . ?
C12 C7 C8 117.5(2) . . ?
C7 C8 F5 120.4(2) . . ?
C9 C8 F5 118.5(2) . . ?
C9 C8 C7 121.2(2) . . ?
C8 C9 F6 118.8(2) . . ?
C10 C9 F6 119.5(2) . . ?
C10 C9 C8 121.7(2) . . ?
C9 C10 C4 120.5(2) . . ?
C11 C10 C4 122.9(2) . . ?
C11 C10 C9 116.5(2) . . ?
C10 C11 F7 119.9(2) . . ?
C12 C11 F7 118.3(2) . . ?
C12 C11 C10 121.9(2) . . ?
C7 C12 F8 120.4(2) . . ?
C11 C12 F8 118.4(2) . . ?
C11 C12 C7 121.2(2) . . ?
C20 N1 C13 117.0(2) . . ?
C15 N2 C14 116.7(2) . . ?
H13 C13 N1 118.87(14) . . ?
C14 C13 N1 122.3(2) . . ?
C14 C13 H13 118.87(14) . . ?
C13 C14 N2 122.4(2) . . ?
H14 C14 N2 118.80(14) . . ?
H14 C14 C13 118.80(14) . . ?
C16 C15 N2 120.0(2) . . ?
C20 C15 N2 120.8(2) . . ?
C20 C15 C16 119.3(2) . . ?
H16 C16 C15 120.14(14) . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.14(15) . . ?
H17 C17 C16 119.68(15) . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.68(15) . . ?
H18 C18 C17 119.62(15) . . ?
C19 C18 C17 120.8(2) . . ?
C19 C18 H18 119.62(15) . . ?
H19 C19 C18 120.08(15) . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.08(14) . . ?
C15 C20 N1 120.8(2) . . ?
C19 C20 N1 119.4(2) . . ?
C19 C20 C15 119.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 F1 -0.2(2) . . . . ?
I1 C1 C2 C3 -177.96(18) . . . . ?
I1 C1 C6 F4 -3.2(2) . . . . ?
I1 C1 C6 C5 177.23(18) . . . . ?
I2 C7 C8 F5 -2.3(2) . . . . ?
I2 C7 C8 C9 177.92(18) . . . . ?
I2 C7 C12 F8 2.9(2) . . . . ?
I2 C7 C12 C11 -176.20(18) . . . . ?
F1 C2 C1 C6 177.6(2) . . . . ?
F1 C2 C3 F2 1.4(2) . . . . ?
F1 C2 C3 C4 -175.7(2) . . . . ?
F2 C3 C2 C1 179.2(2) . . . . ?
F2 C3 C4 C5 179.8(2) . . . . ?
F2 C3 C4 C10 -4.1(3) . . . . ?
F3 C5 C4 C3 -176.6(2) . . . . ?
F3 C5 C4 C10 7.4(3) . . . . ?
F3 C5 C6 F4 -1.2(2) . . . . ?
F3 C5 C6 C1 178.3(2) . . . . ?
F4 C6 C1 C2 179.1(2) . . . . ?
F4 C6 C5 C4 179.7(2) . . . . ?
F5 C8 C7 C12 179.2(2) . . . . ?
F5 C8 C9 F6 -2.8(2) . . . . ?
F5 C8 C9 C10 178.5(2) . . . . ?
F6 C9 C8 C7 177.0(2) . . . . ?
F6 C9 C10 C4 2.1(3) . . . . ?
F6 C9 C10 C11 -176.4(2) . . . . ?
F7 C11 C10 C4 2.2(3) . . . . ?
F7 C11 C10 C9 -179.3(2) . . . . ?
F7 C11 C12 F8 -2.1(2) . . . . ?
F7 C11 C12 C7 176.9(2) . . . . ?
F8 C12 C7 C8 -178.7(2) . . . . ?
F8 C12 C11 C10 179.2(2) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
C1 C6 C5 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 -3.1(3) . . . . ?
C2 C3 C4 C10 172.9(2) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C3 C4 C10 C9 -122.1(2) . . . . ?
C3 C4 C10 C11 56.3(3) . . . . ?
C4 C10 C9 C8 -179.1(2) . . . . ?
C4 C10 C11 C12 -179.1(2) . . . . ?
C7 C8 C9 C10 -1.8(3) . . . . ?
C7 C12 C11 C10 -1.7(3) . . . . ?
C8 C9 C10 C11 2.4(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
N1 C13 C14 N2 0.2(3) . . . . ?
N1 C20 C15 N2 0.2(3) . . . . ?
N1 C20 C15 C16 -179.8(2) . . . . ?
N1 C20 C19 C18 179.9(2) . . . . ?
N2 C15 C16 C17 179.7(2) . . . . ?
N2 C15 C20 C19 -179.9(2) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C15 C20 C19 C18 0.0(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?

