#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:00:11 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243331.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_7243331
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, C10 H8 N2'
_chemical_formula_sum            'C16 H8 Br2 F4 N2'
_chemical_formula_weight         464.056
_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                108.019(5)
_cell_angle_beta                 97.023(5)
_cell_angle_gamma                109.558(4)
_cell_formula_units_Z            1
_cell_length_a                   6.8925(9)
_cell_length_b                   7.6625(10)
_cell_length_c                   8.6230(12)
_cell_measurement_reflns_used    7885
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      28.401
_cell_measurement_theta_min      3.042
_cell_volume                     394.92(9)
_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      99.99
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9934
_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_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.9979
_diffrn_reflns_Laue_measured_fraction_max 0.9934
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9852
_diffrn_reflns_point_group_measured_fraction_full 0.9979
_diffrn_reflns_point_group_measured_fraction_max 0.9934
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    5.174
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0861 before and 0.0455 after correction.
The Ratio of minimum to maximum transmission is 0.6633.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             223.721
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.062
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         0.5052
_refine_diff_density_min         -0.3582
_refine_diff_density_rms         0.0791
_refine_ls_d_res_high            0.7471
_refine_ls_d_res_low             6.6949
_refine_ls_goodness_of_fit_ref   1.0716
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    8
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0716
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0199
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0076P)²+0.3580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0425
_refine_ls_wR_factor_ref         0.0455
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -10
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1832
_reflns_number_total             1966
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce00864a2.cif
_cod_data_source_block           Br2F4bz_22bipy
_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               7243331
_olex2_refinement_description
;
;
_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 0.26484(3) 0.48224(3) 0.62148(3) 0.02591(7) Uani 1.000000 .
F2 F 0.20862(17) 0.21502(17) 0.82927(13) 0.0270(2) Uani 1.000000 .
F1 F 0.00595(18) 0.17940(17) 0.27331(14) 0.0271(2) Uani 1.000000 .
N1 N 0.5413(2) 0.9140(2) 0.66949(19) 0.0207(3) Uani 1.000000 .
C4 C 0.5504(2) 1.0437(3) 0.5922(2) 0.0166(3) Uani 1.000000 .
C2 C 0.0034(3) 0.0927(3) 0.3870(2) 0.0201(3) Uani 1.000000 .
C3 C 0.1061(3) 0.1108(3) 0.6665(2) 0.0193(3) Uani 1.000000 .
C1 C 0.1109(3) 0.2069(3) 0.5535(2) 0.0194(3) Uani 1.000000 .
C8 C 0.6483(3) 1.2498(3) 0.6783(2) 0.0216(4) Uani 1.000000 .
C5 C 0.6340(3) 0.9897(3) 0.8342(2) 0.0255(4) Uani 1.000000 .
C6 C 0.7352(3) 1.1924(3) 0.9298(2) 0.0272(4) Uani 1.000000 .
C7 C 0.7403(3) 1.3243(3) 0.8499(2) 0.0260(4) Uani 1.000000 .
H5 H 0.6304(3) 0.8991(3) 0.8893(2) 0.0306(5) Uiso 1.000000 R
H6 H 0.7992(3) 1.2393(3) 1.0469(2) 0.0327(5) Uiso 1.000000 R
H7 H 0.8061(3) 1.4643(3) 0.9118(2) 0.0312(5) Uiso 1.000000 R
H8 H 0.6519(3) 1.3378(3) 0.6205(2) 0.0259(4) Uiso 1.000000 R
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
C5 N1 C4 117.53(16) . . ?
C4 C4 N1 116.70(19) 2_676 . ?
C8 C4 N1 122.42(16) . . ?
C3 C2 F1 118.66(16) 2_556 . ?
C1 C2 F1 120.01(16) . . ?
C1 C2 C3 121.33(16) . 2_556 ?
C2 C3 F2 119.08(16) 2_556 . ?
C1 C3 F2 120.35(16) . . ?
C1 C3 C2 120.57(16) . 2_556 ?
C2 C1 Br1 120.35(13) . . ?
C3 C1 Br1 121.52(14) . . ?
C3 C1 C2 118.10(16) . . ?
C7 C8 C4 118.79(17) . . ?
H8 C8 C4 120.61(10) . . ?
H8 C8 C7 120.61(11) . . ?
C6 C5 N1 123.98(18) . . ?
H5 C5 N1 118.01(11) . . ?
H5 C5 C6 118.01(11) . . ?
C7 C6 C5 118.03(17) . . ?
H6 C6 C5 120.99(11) . . ?
H6 C6 C7 120.99(11) . . ?
C6 C7 C8 119.24(18) . . ?
H7 C7 C8 120.38(11) . . ?
H7 C7 C6 120.38(11) . . ?
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 1.8720(17) . ?
F2 C3 1.339(2) . ?
F1 C2 1.343(2) . ?
N1 C4 1.347(2) . ?
N1 C5 1.335(2) . ?
C4 C4 1.489(3) 2_676 ?
C4 C8 1.392(2) . ?
C2 C3 1.377(2) 2_556 ?
C2 C1 1.380(3) . ?
C3 C1 1.389(2) . ?
C8 C7 1.387(3) . ?
C8 H8 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
