#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:00:11 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243309.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7243309
loop_
_publ_author_name
'Peloquin, Andrew J.'
'McMillen, Colin D.'
'Pennington, William T.'
_publ_section_title
;
 One dimensional halogen bond design: Br⋯N versus I⋯N with
 fluoroarenes
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              6098
_journal_page_last               6106
_journal_paper_doi               10.1039/D1CE00864A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'Br2 C6 F4, C12 H12 N2'
_chemical_formula_sum            'C18 H12 Br2 F4 N2'
_chemical_formula_weight         492.110
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2021-05-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                82.848(3)
_cell_angle_beta                 82.965(3)
_cell_angle_gamma                75.554(3)
_cell_formula_units_Z            1
_cell_length_a                   6.8796(6)
_cell_length_b                   7.4209(6)
_cell_length_c                   9.2086(8)
_cell_measurement_reflns_used    8219
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.85
_cell_volume                     449.67(7)
_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)'
_diffrn_ambient_temperature      100.0
_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_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_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_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_crystal_density_diffrn    1.817
_exptl_crystal_density_meas      ?
_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'
_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_restrained_S_all      1.0540
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0258
_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
_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)
_cod_data_source_file            d1ce00864a2.cif
_cod_data_source_block           Br2F4bz_44Me222bipy
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7243307--7243335.cif.
;
_cod_database_code               7243309
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
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_
_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'
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_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_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 ?
