#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:00:11 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243318.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_7243318
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, C12 H12 N2'
_chemical_formula_sum            'C24 H12 Br2 F8 N2'
_chemical_formula_weight         640.170
_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
_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                81.781(2)
_cell_angle_beta                 78.260(2)
_cell_angle_gamma                83.082(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7760(4)
_cell_length_b                   10.0737(6)
_cell_length_c                   14.8950(9)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      38.06
_cell_measurement_theta_min      2.34
_cell_volume                     1125.59(11)
_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      100.01
_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_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_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_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      ?
_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'
_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_restrained_S_all      1.0529
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0193
_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
_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)
_cod_data_source_file            d1ce00864a2.cif
_cod_data_source_block           Br2F8bph_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               7243318
_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 0.627267(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_
_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
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 . . ?
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 . ?
