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_7251333
_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:p-dichlorotetrafluorobenzene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                109.370(4)
_cell_angle_beta                 98.590(4)
_cell_angle_gamma                90.299(3)
_cell_formula_units_Z            1
_cell_length_a                   6.3455(3)
_cell_length_b                   7.5012(3)
_cell_length_c                   7.7599(3)
_cell_measurement_reflns_used    4654
_cell_measurement_temperature    130
_cell_measurement_theta_max      74.5670
_cell_measurement_theta_min      6.1070
_cell_volume                     343.95(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 42.94a 64-bit (release 21-06-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_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      130
_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 0.952
_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     80.00 107.00   0.50    3.00    --   50.30  41.00 -37.00   54
  2  \w     96.00 131.00   0.50    3.00    --  102.76  41.00 -37.00   70
  3  \w    135.00 162.00   0.50    3.00    --  102.76  41.00 -37.00   54
  4  \w     65.00 108.00   0.50    3.00    --  102.76 -41.00 169.00   86
  5  \w    -39.00  -8.00   0.50    3.00    --    6.00 123.00-142.86   62
  6  \w    -54.00 -26.00   0.50    3.00    --   14.00 157.00-140.83   56
  7  \w     -4.00  24.00   0.50    3.00    --   22.00  96.00 142.86   56
  8  \w      0.00  25.00   0.50    3.00    --   30.00  99.00 -41.71   50
  9  \w     14.00  39.00   0.50    3.00    --   38.00  85.00  20.63   50
 10  \w     24.00  49.00   0.50    3.00    --   46.00  81.00-110.06   50
 11  \w     18.00  43.00   0.50    3.00    --   46.00  91.00  70.78   50
 12  \w     18.00  55.00   0.50    3.00    --   50.30 -41.00 169.00   74
 13  \w    -10.00  16.00   0.50    3.00    --   50.30 -41.00 169.00   52
 14  \w     27.00  54.00   0.50    3.00    --   50.30 -57.00  60.00   54
 15  \w     -2.00  68.00   0.50    3.00    --   50.30 -77.00  30.00  140
 16  \w    -14.00  15.00   0.50    3.00    --   50.30 -57.00  60.00   58
 17  \w     60.00  98.00   0.50    3.00    --   50.30-125.00  90.00   76
 18  \w     88.00 114.00   0.50    3.00    --   54.00  79.00 173.53   52
 19  \w     32.00  61.00   0.50    3.00    --   54.00  82.00 108.90   58
 20  \w     30.00  56.00   0.50    3.00    --   54.00  20.00 108.84   52
 21  \w     31.00  57.00   0.50    3.00    --   54.00  83.00 -58.48   52
 22  \w     71.00 101.00   0.50    3.00    --   54.00  20.00 108.84   60
 23  \w     33.00  76.00   0.50    3.00    --   54.00  82.00  18.92   86
 24  \w     33.00  62.00   0.50    3.00    --   54.00  79.00 173.53   58
 25  \w     33.00  74.00   0.50    3.00    --   54.00  83.00-105.65   82
 26  \w     39.00  65.00   0.50    3.00    --   62.00  83.00 -39.31   52
 27  \w     40.00  66.00   0.50    3.00    --   62.00  82.00  33.13   52
 28  \w     40.00  65.00   0.50    3.00    --   62.00  82.00 -98.09   50
 29  \w     39.00 121.00   0.50    3.00    --   62.00  83.00-152.00  164
 30  \w     45.00  71.00   0.50    3.00    --   66.00  82.00 157.11   52
 31  \w     48.00  75.00   0.50    3.00    --   66.00  82.00  93.19   54
 32  \w     47.00  82.00   0.50    3.00    --   70.00  83.00 -96.80   70
 33  \w     50.00  76.00   0.50    3.00    --   70.00  82.00-172.15   52
 34  \w     49.00  84.00   0.50    3.00    --   70.00  83.00 118.08   70
 35  \w     48.00  90.00   0.50    3.00    --   70.00  83.00  71.76   84
 36  \w     97.00 130.00   0.50    3.00    --   70.00  82.00 -52.60   66
 37  \w     50.00  91.00   0.50    3.00    --   70.00  82.00 -52.60   82
 38  \w     86.00 112.00   0.50    3.00    --   70.00  83.00 118.08   52
 39  \w     59.00  97.00   0.50    3.00    --   74.00  75.00  -4.84   76
 40  \w     93.00 119.00   0.50    3.00    --   74.00  77.00 170.58   52
 41  \w     55.00  81.00   0.50    3.00    --   74.00  77.00 170.58   52
 42  \w    108.00 137.00   0.50    3.00    --   74.00  76.00  29.56   58
 43  \w     55.00  81.00   0.50    3.00    --   74.00  76.00  29.56   52
 44  \w    107.00 137.00   0.50    3.00    --   74.00  75.00  -4.84   60
 45  \w    102.00 143.00   0.50    3.00    --   74.00  61.00  77.65   82
 46  \w     61.00  95.00   0.50    3.00    --   74.00  61.00  77.65   68
 47  \w    110.00 136.00   0.50    3.00    --   78.00  63.00-107.11   52
 48  \w     64.00  89.00   0.50    3.00    --   78.00  63.00-107.11   50
 49  \w     76.00 152.00   0.50    3.00    --   82.00  43.00 162.84  152
 50  \w     75.00 157.00   0.50    3.00    --   94.00  76.00-102.72  164
 51  \w     44.00 110.00   0.50    3.00    --  102.76 -99.00-180.00  132
 52  \w     38.00  66.00   0.50    3.00    --  102.76-125.00-180.00   56
 53  \w     84.00 141.00   0.50    3.00    --  102.76  77.00 150.00  114
 54  \w     83.00 152.00   0.50    3.00    --  102.76  77.00 -90.00  138
 55  \w     92.00 158.00   0.50    3.00    --  102.76  57.00-150.00  132
 56  \w     83.00 109.00   0.50    3.00    --  102.76  77.00 -60.00   52
 57  \w     90.00 143.00   0.50    3.00    --  102.76  57.00  90.00  106
 58  \w     99.00 145.00   0.50    3.00    --  102.76 125.00-150.00   92
 59  \w    117.00 155.00   0.50    3.00    --  102.76  77.00 -30.00   76
 60  \w     83.00 112.00   0.50    3.00    --  102.76  77.00 -30.00   58
 61  \w     84.00 146.00   0.50    3.00    --  102.76  77.00  90.00  124
 62  \w     84.00 110.00   0.50    3.00    --  102.76  77.00  30.00   52
 63  \w     78.00 109.00   0.50    3.00    --  102.76-125.00  60.00   62
 64  \w     72.00 113.00   0.50    3.00    --  102.76-125.00-180.00   82
 65  \w    109.00 166.00   0.50    3.00    --  102.76 125.00  90.00  114
 66  \w    127.00 163.00   0.50    3.00    --  102.76  77.00   0.00   72
 67  \w     38.00  73.00   0.50    3.00    --  102.76-125.00  60.00   70
 68  \w     92.00 129.00   0.50    3.00    --  102.76  57.00 150.00   74
 69  \w     94.00 153.00   0.50    3.00    --  102.76  57.00  60.00  118
 70  \w     84.00 121.00   0.50    3.00    --  102.76  77.00   0.00   74
 71  \w     95.00 145.00   0.50    3.00    --  102.76  57.00-180.00  100
 72  \w     42.00 112.00   0.50    3.00    --  107.92 -44.00-114.68  140
 73  \w     53.00 105.00   0.50    3.00    --  107.92-100.00  99.23  104
 74  \w     66.00 109.00   0.50    3.00    --  107.92-116.00 -61.20   86
 75  \w     37.00  81.00   0.50    3.00    --  107.92 -52.00-158.19   88
 76  \w     47.00  74.00   0.50    3.00    --  107.92-109.00  31.92   54
 77  \w     38.00 115.00   0.50    3.00    --  107.92 -52.00  93.59  154
 78  \w     44.00 110.00   0.50    3.00    --  107.92 -45.00 -35.80  132
;
_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      -0.1012336000
_diffrn_orient_matrix_UB_12      -0.1745514000
_diffrn_orient_matrix_UB_13      -0.1626928000
_diffrn_orient_matrix_UB_21      0.0078229000
_diffrn_orient_matrix_UB_22      0.1112112000
_diffrn_orient_matrix_UB_23      -0.1341612000
_diffrn_orient_matrix_UB_31      0.2240224000
_diffrn_orient_matrix_UB_32      -0.0687053000
_diffrn_orient_matrix_UB_33      -0.0313450000
_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  0.0331
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6746
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.556
_diffrn_reflns_theta_min         6.124
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.575
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.143
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_description       block
_exptl_crystal_F_000             164
_exptl_crystal_preparation
'Components mixed in 50:50 molar ratio at 1/100 mole scale'
_exptl_crystal_recrystallization_method
'Crystals grown in situ and coooled slowly through phase transitions'
_exptl_crystal_size_max          0.875
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.211
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0707P)^2^+0.2053P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1293
_reflns_number_total             1413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00989h2.cif
_cod_data_source_block           exp_696
_cod_database_code               7251333
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C14 H10 F4 Cl2'
_chemical_oxdiff_usercomment     'Same capillary as for phase II'
_shelx_estimated_absorpt_t_max   0.445
_shelx_estimated_absorpt_t_min   0.108
_olex2_refinement_description
;
;
_shelx_res_checksum              91298
_olex2_exptl_crystal_mounting_method '0.2mm 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 3.675
_oxdiff_exptl_absorpt_empirical_full_min 0.520