Exploring non-covalent interactions in binary aromatic complexes
Bear, Joseph C.; Cockcroft, Jeremy Karl; Rosu-Finsen, Alexander; Williams, Jeffrey Huw; CrystEngComm  (2025) –; doi:10.1039/D5CE00989H

data_7251329
_publ_section_title
;
 Exploring non-covalent interactions in binary aromatic complexes
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00989H
_journal_year                    2025
_chemical_formula_moiety         'Br2 C6 F4, C8 H10'
_chemical_formula_sum            'C14 H10 Br2 F4'
_chemical_formula_weight         414.04
_chemical_name_systematic        p-Xylene:1,4-dibromotetrafluorobenzene
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-30
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.357(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4576(3)
_cell_length_b                   8.3594(3)
_cell_length_c                   9.8748(3)
_cell_measurement_reflns_used    3662
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.2550
_cell_measurement_theta_min      4.4310
_cell_volume                     697.56(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_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      8.00  33.00   1.00    1.00    --   42.00  83.00 -72.84   25
  2  \w    -70.00   9.00   1.00    1.00    --  -42.37  57.00-120.00   79
  3  \w   -115.00 -88.00   1.00    1.00    --  -42.37 -57.00 150.00   27
  4  \w    -56.00 -14.00   1.00    1.00    --  -42.37 -57.00 150.00   42
  5  \w     18.00  44.00   1.00    1.00    --   42.37  38.00 -90.00   26
  6  \w      8.00  33.00   1.00    1.00    --   42.37  83.00  80.31   25
  7  \w     75.00 115.00   1.00    1.00    --   42.37  38.00 -90.00   40
  8  \w     29.00  93.00   1.00    1.00    --   42.37-125.00  60.00   64
  9  \w     16.00  41.00   1.00    1.00    --   50.00  82.00  94.15   25
 10  \w     16.00  41.00   1.00    1.00    --   50.00  82.00 -31.70   25
 11  \w     16.00  41.00   1.00    1.00    --   50.00  82.00-123.30   25
 12  \w     16.00  41.00   1.00    1.00    --   50.00  82.00  19.35   25
 13  \w     16.00  41.00   1.00    1.00    --   50.00  82.00 169.56   25
 14  \w     35.00  70.00   1.00    1.00    --   54.00  65.00 -48.84   35
 15  \w     99.00 126.00   1.00    1.00    --   54.00  65.00 -48.84   27
 16  \w     76.00 106.00   1.00    1.00    --   58.00  71.00  64.05   30
 17  \w     28.00  53.00   1.00    1.00    --   58.00  71.00  64.05   25
 18  \w     30.00  68.00   1.00    1.00    --   58.00  67.00 -98.07   38
 19  \w     35.00  69.00   1.00    1.00    --   62.00  71.00-172.82   34
 20  \w     36.00  64.00   1.00    1.00    --   62.00  58.00  38.78   28
 21  \w     98.00 130.00   1.00    1.00    --   62.00  71.00-172.82   32
 22  \w     44.00  70.00   1.00    1.00    --   70.00  70.00 122.05   26
 23  \w    113.00 139.00   1.00    1.00    --   70.00  70.00 122.05   26
 24  \w     44.00  73.00   1.00    1.25    --   74.00  67.00 110.47   29
 25  \w    103.00 140.00   1.00    1.25    --   74.00  69.00  63.21   37
 26  \w     45.00  91.00   1.00    1.25    --   74.00  69.00  63.21   46
 27  \w     49.00  86.00   1.00    1.25    --   78.00  71.00 -39.15   37
 28  \w     56.00  87.00   1.00    1.25    --   82.00  58.00 172.47   31
 29  \w     56.00  81.00   1.00    1.25    --   86.00  70.00 129.57   25
 30  \w     61.00 162.00   1.00    1.25    --   90.00  66.00-108.95  101
 31  \w     69.00  96.00   1.00    1.25    --   94.00  54.00 179.20   27
 32  \w    111.00 173.00   1.00    1.25    --  103.86  77.00-150.00   62
 33  \w     32.00 101.00   1.00    1.25    --  103.86-125.00  30.00   69
 34  \w     35.00 130.00   1.00    1.25    --  103.86 -61.00  90.00   95
 35  \w     76.00 169.00   1.00    1.25    --  103.86  61.00   0.00   93
 36  \w    125.00 176.00   1.00    1.25    --  103.86  61.00 -60.00   51
 37  \w     79.00 120.00   1.00    1.25    --  103.86  61.00 -60.00   41
 38  \w     27.00 104.00   1.00    1.25    --  103.86 -95.00  60.00   77
 39  \w     31.00 112.00   1.00    1.25    --  103.86-125.00 -60.00   81
 40  \w     82.00 109.00   1.00    1.25    --  103.86  61.00  30.00   27
 41  \w     78.00 109.00   1.00    1.25    --  103.86  61.00 -30.00   31
 42  \w     77.00 173.00   1.00    1.25    --  103.86  50.00  91.28   96
 43  \w    126.00 160.00   1.00    1.25    --  103.86 125.00  60.00   34
 44  \w     76.00 175.00   1.00    1.25    --  103.86  61.00 150.00   99
 45  \w     75.00 102.00   1.00    1.25    --  103.86  61.00-180.00   27
 46  \w     76.00 103.00   1.00    1.25    --  103.86  61.00 -90.00   27
 47  \w     75.00 124.00   1.00    1.25    --  103.86  61.00-150.00   49
 48  \w    103.00 133.00   1.00    1.25    --  103.86  61.00  60.00   30
 49  \w     77.00 102.00   1.00    1.25    --  103.86  61.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1181618000
_diffrn_orient_matrix_UB_12      0.1404863000
_diffrn_orient_matrix_UB_13      0.0058897000
_diffrn_orient_matrix_UB_21      -0.0264709000
_diffrn_orient_matrix_UB_22      0.0200976000
_diffrn_orient_matrix_UB_23      0.1524645000
_diffrn_orient_matrix_UB_31      0.1362399000
_diffrn_orient_matrix_UB_32      -0.1176314000
_diffrn_orient_matrix_UB_33      0.0331412000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4773
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.494
_diffrn_reflns_theta_min         4.481
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.971
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_preparation       '1:1 molar mixture (0.01 moles)'
_exptl_crystal_recrystallization_method
'Grown from the melt in the bottle left in the fridge'
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     53
_refine_ls_number_reflns         738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0206
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0275P)^2^+0.7840P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                713
_reflns_number_total             738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00989h2.cif
_cod_data_source_block           exp_3040
_cod_database_code               7251329
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C8 H10 C6 F4 Br2 '
_chemical_oxdiff_usercomment     C6F4Br2+p-xylene
_shelx_estimated_absorpt_t_max   0.461
_shelx_estimated_absorpt_t_min   0.370
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H5A(0.5) H5B(0.5) H5C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_shelx_res_checksum              8381
_olex2_date_sample_data_collection 2022-02-07
_olex2_exptl_crystal_mounting_method '0.3mm Hampton research nylon loop'
_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 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.491