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_7251335
_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         'C6 Cl2 F4, C8 H10'
_chemical_formula_sum            'C14 H10 Cl2 F4'
_chemical_formula_weight         325.12
_chemical_name_systematic        p-xylene:dichlorotetrafluorobenzene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2n'
_space_group_name_H-M_alt        'P 1 1 21/n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2025-08-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                96.4553(11)
_cell_formula_units_Z            2
_cell_length_a                   14.83539(17)
_cell_length_b                   7.90142(9)
_cell_length_c                   5.98834(7)
_cell_measurement_reflns_used    11619
_cell_measurement_temperature    220
_cell_measurement_theta_max      76.8600
_cell_measurement_theta_min      5.6510
_cell_volume                     697.507(14)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.998
_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     45.00  70.00   0.50    2.00    --   50.30-132.00 -35.00   50
  2  \w     59.00 100.00   0.50    2.00    --   50.30-138.00 148.00   82
  3  \w    101.00 127.00   0.50    2.00    --  102.76-138.00 148.00   52
  4  \w     95.00 121.00   0.50    2.00    --  102.76-132.00 -35.00   52
  5  \w    125.00 152.00   0.50    2.00    --  102.76 138.00-149.00   54
  6  \w     88.00 155.00   0.50    2.00    --  102.76 132.00  34.00  134
  7  \w    -43.00 -14.00   0.50    2.00    --    6.00 126.00  -3.26   58
  8  \w    -35.00  -3.00   0.50    2.00    --    6.00 115.00  66.98   64
  9  \w    -49.00 -23.00   0.50    2.00    --   14.00 149.00  14.50   52
 10  \w     -9.00  16.00   0.50    2.00    --   22.00  98.00-178.68   50
 11  \w      3.00  31.00   0.50    2.00    --   34.00  97.00  22.31   56
 12  \w      5.00  37.00   0.50    2.00    --   34.00  93.00 166.90   64
 13  \w     17.00  43.00   0.50    2.00    --   42.00  91.00-160.23   52
 14  \w     16.00  41.00   0.50    2.00    --   42.00  88.00  -8.63   50
 15  \w     15.00  46.00   0.50    2.00    --   42.00  90.00 100.01   62
 16  \w     15.00  61.00   0.50    2.00    --   50.30 -57.00   0.00   92
 17  \w     -5.00  63.00   0.50    2.00    --   50.30 -57.00-120.00  136
 18  \w     73.00  98.00   0.50    2.00    --   50.30  19.00 -30.00   50
 19  \w     25.00  62.00   0.50    2.00    --   50.30  19.00 -30.00   74
 20  \w      5.00  59.00   0.50    2.00    --   50.30 -57.00 120.00  108
 21  \w     31.00  57.00   0.50    2.00    --   54.00  83.00  70.94   52
 22  \w     67.00 108.00   0.50    2.00    --   54.00  83.00  70.94   82
 23  \w     32.00  62.00   0.50    2.00    --   54.00  82.00  30.62   60
 24  \w     84.00 110.00   0.50    2.00    --   54.00  83.00 -26.02   52
 25  \w     31.00  57.00   0.50    2.00    --   54.00  83.00 -26.02   52
 26  \w     32.00  58.00   0.50    2.00    --   54.00  82.00 -89.34   52
 27  \w     35.00  69.00   0.50    2.00    --   58.00  83.00 166.00   68
 28  \w     86.00 112.00   0.50    2.00    --   58.00  83.00 129.64   52
 29  \w     35.00  61.00   0.50    2.00    --   58.00  83.00 129.64   52
 30  \w     36.00  83.00   0.50    2.00    --   58.00  81.00-159.73   94
 31  \w     83.00 118.00   0.50    2.00    --   58.00  83.00-120.64   70
 32  \w     35.00  73.00   0.50    2.00    --   58.00  83.00-120.64   76
 33  \w     41.00  74.00   0.50    2.00    --   62.00  82.00 -23.39   66
 34  \w     43.00  69.00   0.50    2.00    --   66.00  83.00  92.65   52
 35  \w     92.00 125.00   0.50    2.00    --   66.00  82.00  40.79   66
 36  \w     94.00 125.00   0.50    2.00    --   66.00  83.00  92.65   62
 37  \w     44.00  77.00   0.50    2.00    --   66.00  82.00  40.79   66
 38  \w     44.00  69.00   0.50    2.00    --   66.00  81.00 -66.51   50
 39  \w     44.00  74.00   0.50    2.00    --   66.00  82.00-106.88   60
 40  \w     43.00  79.00   0.50    2.00    --   66.00  83.00 175.88   72
 41  \w     48.00  78.00   0.50    2.00    --   70.00  82.00-150.94   60
 42  \w     47.00  76.00   0.50    2.00    --   70.00  83.00 111.86   58
 43  \w    112.00 139.00   0.50    2.00    --   74.00  71.00-105.57   54
 44  \w     58.00  86.00   0.50    2.00    --   74.00  71.00-105.57   56
 45  \w    111.00 136.00   0.50    2.00    --   74.00  79.00  57.78   50
 46  \w     53.00  86.00   0.50    2.00    --   74.00  79.00  57.78   66
 47  \w     63.00  89.00   0.50    2.00    --   78.00  66.00 -40.58   52
 48  \w     56.00 100.00   0.50    2.00    --   78.00  82.00 -10.48   88
 49  \w    102.00 146.00   0.50    2.00    --   82.00  68.00 144.19   88
 50  \w     66.00 146.00   0.50    2.00    --   82.00  71.00 -32.72  160
 51  \w     67.00  92.00   0.50    2.00    --   82.00  68.00 144.19   50
 52  \w     71.00 109.00   0.50    2.00    --   86.00  68.00  85.33   76
 53  \w     65.00 148.00   0.50    2.00    --   86.00  79.00 155.13  166
 54  \w     64.00 145.00   0.50    2.00    --   86.00  82.00-175.28  162
 55  \w     66.00 148.00   0.50    2.00    --   86.00  78.00  -2.74  164
 56  \w    122.00 152.00   0.50    2.00    --   86.00  68.00  85.33   60
 57  \w    116.00 158.00   0.50    2.00    --   90.00  64.00 -87.44   84
 58  \w     76.00 103.00   0.50    2.00    --   90.00  64.00 -87.44   54
 59  \w    140.00 172.00   0.50    2.00    --  102.76  57.00-120.00   64
 60  \w     99.00 135.00   0.50    2.00    --  102.76  57.00-120.00   72
 61  \w     41.00 109.00   0.50    2.00    --  102.76 -99.00  30.00  136
 62  \w     40.00 109.00   0.50    2.00    --  102.76-125.00  30.00  138
 63  \w    137.00 162.00   0.50    2.00    --  102.76  77.00 -60.00   50
 64  \w     83.00 142.00   0.50    2.00    --  102.76  77.00  30.00  118
 65  \w    132.00 165.00   0.50    2.00    --  102.76  77.00 -90.00   66
 66  \w     83.00 110.00   0.50    2.00    --  102.76  77.00 -90.00   54
 67  \w     84.00 113.00   0.50    2.00    --  102.76  77.00 -60.00   58
 68  \w    135.00 160.00   0.50    2.00    --  102.76  77.00-150.00   50
 69  \w     83.00 108.00   0.50    2.00    --  102.76  77.00-150.00   50
 70  \w     41.00 100.00   0.50    2.00    --  102.76-125.00 -90.00  118
 71  \w    136.00 162.00   0.50    2.00    --  102.76  77.00  90.00   52
 72  \w    119.00 163.00   0.50    2.00    --  102.76  77.00-180.00   88
 73  \w     98.00 172.00   0.50    2.00    --  102.76  57.00 -30.00  148
 74  \w     83.00 152.00   0.50    2.00    --  102.76  77.00 120.00  138
 75  \w     83.00 109.00   0.50    2.00    --  102.76  77.00  90.00   52
 76  \w     86.00 111.00   0.50    2.00    --  102.76  77.00-180.00   50
 77  \w     90.00 116.00   0.50    2.00    --  102.76  57.00  30.00   52
 78  \w     58.00 103.00   0.50    2.00    --  102.76 -99.00 120.00   90
 79  \w     41.00  93.00   0.50    2.00    --  107.92 -41.00 174.69  104
 80  \w     37.00 118.00   0.50    2.00    --  107.92 -52.00 -85.09  162
 81  \w     40.00 111.00   0.50    2.00    --  107.92 -44.00  92.05  142
 82  \w     50.00 107.00   0.50    2.00    --  107.92 -93.00 150.94  114
 83  \w     45.00 110.00   0.50    2.00    --  107.92-113.00 -39.62  130
 84  \w     44.00  89.00   0.50    2.00    --  107.92 -43.00   5.15   90
 85  \w     48.00 107.00   0.50    2.00    --  107.92 -95.00  49.67  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0169608008
_diffrn_orient_matrix_UB_12      0.1266081806
_diffrn_orient_matrix_UB_13      -0.1869836433
_diffrn_orient_matrix_UB_21      -0.0069168792
_diffrn_orient_matrix_UB_22      0.1403264041
_diffrn_orient_matrix_UB_23      0.1757369454
_diffrn_orient_matrix_UB_31      0.1028810212
_diffrn_orient_matrix_UB_32      0.0526937368
_diffrn_orient_matrix_UB_33      -0.0189181850
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0088
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            15518
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.399
_diffrn_reflns_theta_min         6.004
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.512
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.122
_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    1.548
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_preparation       '50:50 molar mixture'
_exptl_crystal_recrystallization_method 'Grown in situ'
_exptl_crystal_size_max          0.931
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.218
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1460
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0576P)^2^+0.0693P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0901
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1371
_reflns_number_total             1460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00989h2.cif
_cod_data_source_block           exp_692
_cod_database_code               7251335
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C14 H10 F4 Cl2'
_chemical_oxdiff_usercomment     '0.2mm capillary new sample made 4/4/24'
_shelx_estimated_absorpt_t_max   0.440
_shelx_estimated_absorpt_t_min   0.102
_olex2_refinement_description
;
1. Restrained distances
 C7-H7A \\sim C7-H7B \\sim C7-H7C
 with sigma of 0.02
 H7A-H7B \\sim H7B-H7C \\sim H7C-H7A
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uiso(H7A) = Uiso(H7B) = Uiso(H7C)
;
_shelx_res_checksum              97941
_olex2_exptl_crystal_mounting_method '0.2mm diameter X-ray capillary'
_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 3.316
_oxdiff_exptl_absorpt_empirical_full_min 0.740