One dimensional halogen bond design: Br⋯N versus I⋯N with fluoroarenes
Peloquin, Andrew J.; McMillen, Colin D.; Pennington, William T.; CrystEngComm 23 (2021) 6098–6106; doi:10.1039/D1CE00864A

data_7243314
_publ_section_title
;
 One dimensional halogen bond design: Br&#x22EF;N versus I&#x22EF;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, C6 H8 N2'
_chemical_formula_sum            'C12 H8 Br2 F4 N2'
_chemical_formula_weight         416.011
_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                83.796(3)
_cell_angle_beta                 84.121(3)
_cell_angle_gamma                79.072(3)
_cell_formula_units_Z            1
_cell_length_a                   4.8003(2)
_cell_length_b                   6.6036(2)
_cell_length_c                   10.9521(4)
_cell_measurement_reflns_used    16909
_cell_measurement_temperature    106(8)
_cell_measurement_theta_max      28.9760
_cell_measurement_theta_min      1.8630
_cell_volume                     337.69(2)
_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)'
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -13.00  83.00   0.50    0.31    --   14.30  77.00 -90.00  192
  2  \w    -13.00  83.00   0.50    0.31    --   14.30  77.00 -60.00  192
  3  \w    -13.00  84.00   0.50    0.31    --   14.30  78.00 134.00  194
  4  \w     -8.00  82.00   0.50    0.31    --   14.30  61.00 150.00  180
  5  \w     -3.00  82.00   0.50    0.31    --   14.30  45.00 120.00  170
  6  \w     -3.00  82.00   0.50    0.31    --   14.30  45.00  90.00  170
  7  \w    -16.00  89.00   0.50    0.31    --   14.30  15.00 150.00  210
  8  \w    -16.00  89.00   0.50    0.31    --   14.30  15.00  60.00  210
  9  \w    -62.00   6.00   0.50    0.31    --   14.30   0.00 -30.00  136
 10  \w    -16.00  89.00   0.50    0.31    --   14.30  15.00 -60.00  210
 11  \w    -62.00  90.00   0.50    0.31    --   14.30   0.00 -90.00  304
 12  \w    -62.00  90.00   0.50    0.31    --   14.30   0.00 -60.00  304
 13  \w    -62.00  90.00   0.50    0.31    --   14.30   0.00-120.00  304
 14  \w    -62.00  90.00   0.50    0.31    --   14.30   0.00-180.00  304
 15  \w    -62.00  90.00   0.50    0.31    --   14.30   0.00-150.00  304
 16  \w    -66.00  -9.00   0.50    0.31    --  -15.63 125.00 -60.00  114
 17  \w    -66.00  -9.00   0.50    0.31    --  -15.63 125.00 -90.00  114
 18  \w    -66.00  -9.00   0.50    0.31    --  -15.63 125.00-150.00  114
 19  \w    -66.00  -9.00   0.50    0.31    --  -15.63 125.00 -30.00  114
 20  \w    -66.00  -9.00   0.50    0.31    --  -15.63 125.00  60.00  114
 21  \w    -66.00  -9.00   0.50    0.31    --  -15.63 125.00 150.00  114
 22  \w    -43.00  54.00   0.50    0.31    --  -15.63  78.00 134.00  194
 23  \w    -42.00  53.00   0.50    0.31    --  -15.63  77.00  60.00  190
 24  \w    -28.00  53.00   0.50    0.31    --  -15.63  30.00 -60.00  162
 25  \w    -28.00  53.00   0.50    0.31    --  -15.63  30.00 -90.00  162
 26  \w    -60.00   3.00   0.50    0.31    --   14.30 -15.00   0.00  126
 27  \w    -54.00  14.00   0.50    0.31    --   14.30 -30.00 -60.00  136
 28  \w    -53.00  37.00   0.50    0.31    --   14.30 -61.00 -30.00  180
 29  \w    -55.00  42.00   0.50    0.31    --   14.30 -78.00   8.00  194
 30  \w    -54.00  14.00   0.50    0.31    --   14.30 -30.00  60.00  136
 31  \w    -60.00   3.00   0.50    0.31    --   14.30 -15.00 150.00  126
 32  \w    -84.00  -3.00   0.50    0.31    --  -15.63 -30.00 150.00  162
 33  \w    -82.00   2.00   0.50    0.31    --  -15.63 -45.00 150.00  168
 34  \w    -84.00  12.00   0.50    0.31    --  -15.63 -78.00   8.00  192
 35  \w    -82.00   2.00   0.50    0.31    --  -15.63 -45.00 -90.00  168
 36  \w      9.00  65.00   0.50    0.31    --   14.30-125.00 -30.00  112
 37  \w      9.00  65.00   0.50    0.31    --   14.30-125.00-150.00  112
 38  \w      9.00  65.00   0.50    0.31    --   14.30-125.00 -90.00  112
 39  \w      9.00  65.00   0.50    0.31    --   14.30-125.00 -60.00  112
 40  \w      9.00  65.00   0.50    0.31    --   14.30-125.00 120.00  112
 41  \w    -38.00  47.00   0.50    0.31    --   14.30 -94.00 150.00  170
 42  \w    -38.00  17.00   0.50    0.31    --  -15.63 -94.00 -30.00  110
 43  \w    -38.00  17.00   0.50    0.31    --  -15.63 -94.00   0.00  110
 44  \w    -38.00  17.00   0.50    0.31    --  -15.63 -94.00 120.00  110
 45  \w    -38.00  17.00   0.50    0.31    --  -15.63 -94.00 -60.00  110
 46  \w    -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       '\w 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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_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
_exptl_crystal_size_max          0.688
_exptl_crystal_size_mid          0.475
_exptl_crystal_size_min          0.349
_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_restrained_S_all      1.0432
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0280
_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/[\s^2^(Fo^2^)+(0.0297P)^2^+0.0849P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0626
_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_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce00864a2.cif
_cod_data_source_block           Br2F4bz_25Me2pyrz
_cod_depositor_comments
'Adding full bibliography for 7243307--7243335.cif.'
_cod_database_code               7243314
_chemical_oxdiff_formula         (Br2F4C6)(N2C6H8)
_chemical_oxdiff_usercomment     (I2F8bph)(Me3pyrz)
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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)
;
_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