#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:00:11 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243317.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_7243317
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 C12 F8, C8 H12 N2'
_chemical_formula_sum            'C20 H12 Br2 F8 N2'
_chemical_formula_weight         592.126
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     dual
_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                90
_cell_angle_beta                 102.784(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3837(9)
_cell_length_b                   13.8699(10)
_cell_length_c                   11.1754(8)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      2.61
_cell_volume                     2023.1(2)
_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 0.9907
_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_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_source                   'fine focus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_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      ?
_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'
_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_restrained_S_all      1.0309
_refine_ls_R_factor_all          0.0179
_refine_ls_R_factor_gt           0.0162
_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
_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)
_cod_data_source_file            d1ce00864a2.cif
_cod_data_source_block           Br2F8bph_Me4pyrZ
_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_original_cell_volume        2023.1(3)
_cod_database_code               7243317
_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+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
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_
_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
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) . . ?
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 . ?
