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_7251332
_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         'Br C6 F5, C8 H10'
_chemical_formula_sum            'C14 H10 Br F5'
_chemical_formula_weight         353.13
_chemical_name_systematic        p-xylene:bromopentafluorobenzene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-16
_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                 99.229(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0813(3)
_cell_length_b                   15.2034(4)
_cell_length_c                   9.8653(2)
_cell_measurement_reflns_used    13139
_cell_measurement_temperature    120
_cell_measurement_theta_max      72.1460
_cell_measurement_theta_min      4.9230
_cell_volume                     1344.44(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.977
_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     -5.00  20.00   1.00    1.00    --   34.00  94.00 127.45   25
  2  \w     -4.00  21.00   1.00    1.00    --   34.00  91.00-144.46   25
  3  \w   -116.00 -78.00   1.00    1.00    --  -42.37 -38.00  90.00   38
  4  \w    -53.00 -16.00   1.00    1.00    --  -42.37 -57.00   0.00   37
  5  \w   -108.00 -59.00   1.00    1.00    --  -42.37 -57.00   0.00   49
  6  \w    -62.00 -21.00   1.00    1.00    --  -42.37 -38.00  90.00   41
  7  \w    -71.00  31.00   1.00    1.00    --  -42.37  57.00 150.00  102
  8  \w     50.00 121.00   1.00    1.00    --   42.37  19.00-150.00   71
  9  \w     27.00  95.00   1.00    1.00    --   42.37-125.00 -30.00   68
 10  \w      3.00  47.00   1.00    1.00    --   42.37  19.00-150.00   44
 11  \w     12.00  39.00   1.00    1.00    --   46.00  81.00 134.49   27
 12  \w     16.00  41.00   1.00    1.00    --   50.00  82.00-169.99   25
 13  \w     16.00  42.00   1.00    1.00    --   50.00  82.00-124.17   26
 14  \w     16.00  42.00   1.00    1.00    --   50.00  81.00 -27.24   26
 15  \w     16.00  41.00   1.00    1.00    --   50.00  82.00  49.70   25
 16  \w     31.00  72.00   1.00    1.00    --   62.00  71.00 -55.71   41
 17  \w    105.00 140.00   1.00    1.00    --   66.00  71.00   3.87   35
 18  \w     86.00 113.00   1.00    1.00    --   66.00  69.00 152.09   27
 19  \w     35.00  61.00   1.00    1.00    --   66.00  71.00   3.87   26
 20  \w     36.00  61.00   1.00    1.00    --   66.00  70.00-119.35   25
 21  \w     36.00  63.00   1.00    1.00    --   66.00  69.00 152.09   27
 22  \w    111.00 138.00   1.00    1.00    --   70.00  69.00 175.79   27
 23  \w     43.00  75.00   1.00    1.00    --   70.00  70.00-172.19   32
 24  \w    105.00 139.00   1.00    1.00    --   70.00  69.00  60.28   34
 25  \w     39.00  72.00   1.00    1.00    --   70.00  69.00  60.28   33
 26  \w     41.00  73.00   1.00    1.00    --   70.00  66.00 129.14   32
 27  \w     39.00  66.00   1.00    1.00    --   70.00  69.00 175.79   27
 28  \w     44.00  71.00   1.00    1.24    --   74.00  70.00 -97.60   27
 29  \w     44.00  72.00   1.00    1.24    --   74.00  70.00 -68.52   28
 30  \w     45.00  71.00   1.00    1.24    --   74.00  61.00 103.73   26
 31  \w     49.00  74.00   1.00    1.24    --   78.00  68.00  16.27   25
 32  \w     53.00  91.00   1.00    1.24    --   82.00  64.00  40.60   38
 33  \w     51.00  77.00   1.00    1.24    --   82.00  71.00-123.08   26
 34  \w    117.00 158.00   1.00    1.24    --   90.00  60.00-178.81   41
 35  \w     62.00  96.00   1.00    1.24    --   90.00  60.00-178.81   34
 36  \w    117.00 173.00   1.00    1.24    --  102.00  69.00 -60.24   56
 37  \w     72.00  97.00   1.00    1.24    --  102.00  69.00 -60.24   25
 38  \w     24.00 106.00   1.00    1.24    --  103.86 -95.00 -90.00   82
 39  \w     36.00 113.00   1.00    1.24    --  103.86-125.00 150.00   77
 40  \w     40.00  72.00   1.00    1.24    --  103.86 -61.00 120.00   32
 41  \w     75.00 141.00   1.00    1.24    --  103.86  61.00 150.00   66
 42  \w     75.00 174.00   1.00    1.24    --  103.86  61.00  90.00   99
 43  \w    115.00 177.00   1.00    1.24    --  103.86  65.00   1.92   62
 44  \w     75.00 100.00   1.00    1.24    --  103.86  65.00   1.92   25
 45  \w     80.00 117.00   1.00    1.24    --  103.86  45.00 150.00   37
 46  \w     82.00 173.00   1.00    1.24    --  103.86  68.00 171.29   91
 47  \w     75.00 175.00   1.00    1.24    --  103.86  61.00-150.00  100
 48  \w     76.00 176.00   1.00    1.24    --  103.86  61.00 -90.00  100
 49  \w     33.00 129.00   1.00    1.24    --  103.86 -45.00-120.00   96
 50  \w     77.00 143.00   1.00    1.24    --  103.86  61.00 -30.00   66
 51  \w     76.00 101.00   1.00    1.24    --  103.86  61.00 -65.90   25
 52  \w     75.00 105.00   1.00    1.24    --  103.86  61.00  30.00   30
 53  \w     76.00 103.00   1.00    1.24    --  103.86  63.00 109.57   27
 54  \w     75.00 152.00   1.00    1.24    --  103.86  61.00  60.00   77
 55  \w     39.00  88.00   1.00    1.24    --  103.86 -77.00  30.00   49
 56  \w    124.00 150.00   1.00    1.24    --  103.86  61.00-120.00   26
 57  \w     76.00 101.00   1.00    1.24    --  103.86  61.00-120.00   25
 58  \w     91.00 118.00   1.00    1.24    --  103.86 -61.00 120.00   27
 59  \w     32.00 112.00   1.00    1.24    --  103.86-125.00-120.00   80
 60  \w     57.00 103.00   1.00    1.24    --  103.86 -95.00   0.00   46
;
_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      0.1059621000
_diffrn_orient_matrix_UB_12      0.0067763000
_diffrn_orient_matrix_UB_13      0.1381370000
_diffrn_orient_matrix_UB_21      -0.0571378000
_diffrn_orient_matrix_UB_22      -0.0893365000
_diffrn_orient_matrix_UB_23      0.0439766000
_diffrn_orient_matrix_UB_31      0.1226755000
_diffrn_orient_matrix_UB_32      -0.0473852000
_diffrn_orient_matrix_UB_33      -0.0632558000
_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  0.0975
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22028
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.038
_diffrn_reflns_theta_min         5.395
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.628
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.102
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
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_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_preparation       '1:1 molar ratio'
_exptl_crystal_recrystallization_method
'Crystal grown in 0.3mm capillary in situ'
_exptl_crystal_size_max          0.95
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.315
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+0.5565P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2381
_reflns_number_total             2624
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00989h2.cif
_cod_data_source_block           exp_3187
_cod_original_cell_volume        1344.42(6)
_cod_database_code               7251332
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C8 H10 C6 F5 Br'
_chemical_oxdiff_usercomment
'0.3mm capillary 1:1 molar ratio grown at about 260K'
_shelx_estimated_absorpt_t_max   0.323
_shelx_estimated_absorpt_t_min   0.096
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              84487
_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 61.167
_oxdiff_exptl_absorpt_empirical_full_min 0.351