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_7251327
_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 Cl F5, C8 H10'
_chemical_formula_sum            'C14 H10 Cl F5'
_chemical_formula_weight         308.67
_chemical_name_systematic        p-xylene:chloropentafluorobenzene
_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             2024-11-25
_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                109.801(5)
_cell_angle_beta                 99.549(5)
_cell_angle_gamma                95.567(5)
_cell_formula_units_Z            1
_cell_length_a                   6.2099(4)
_cell_length_b                   7.4687(4)
_cell_length_c                   7.9874(4)
_cell_measurement_reflns_used    2961
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.2830
_cell_measurement_theta_min      5.9600
_cell_volume                     339.00(4)
_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      200
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.939
_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     38.00  76.00   0.50    3.00    --   49.93-131.00  83.00   76
  2  \w     61.00  88.00   0.50    3.00    --   49.93-139.00 -90.00   54
  3  \w    107.00 132.00   0.50   12.00    --  102.88 131.00 155.00   50
  4  \w    112.00 138.00   0.50   12.00    --  102.88 139.00 -30.00   52
  5  \w     65.00  90.00   0.50   12.00    --  102.88-139.00 -90.00   50
  6  \w     86.00 114.00   0.50   12.00    --  102.88-131.00  83.00   56
  7  \w    -57.00 -30.00   0.50    3.00    --   14.00 160.00-103.18   54
  8  \w    -56.00 -31.00   0.50    3.00    --   14.00 158.00 106.74   50
  9  \w    -53.00 -28.00   0.50    3.00    --   14.00 153.00  -1.08   50
 10  \w      8.00  40.00   0.50    3.00    --   30.00  82.00  24.17   64
 11  \w      1.00  26.00   0.50    3.00    --   30.00  93.00 144.12   50
 12  \w     38.00  79.00   0.50    3.00    --   49.93 -99.00-120.00   82
 13  \w      8.00  52.00   0.50    3.00    --   49.93 -77.00  30.00   88
 14  \w     31.00  56.00   0.50    3.00    --   49.93  77.00 120.00   50
 15  \w     -6.00  45.00   0.50    3.00    --   49.93 -77.00 -90.00  102
 16  \w     39.00  68.00   0.50    3.00    --   49.93  19.00-180.00   58
 17  \w     30.00  56.00   0.50    3.00    --   49.93  77.00-120.00   52
 18  \w     30.00  71.00   0.50    3.00    --   49.93  77.00 -90.00   82
 19  \w     30.00  56.00   0.50    3.00    --   49.93  77.00  90.00   52
 20  \w     36.00  79.00   0.50    3.00    --   54.00  77.00-179.95   86
 21  \w     90.00 117.00   0.50    3.00    --   54.00  77.00-179.95   54
 22  \w     37.00  64.00   0.50    3.00    --   54.00  76.00  18.96   54
 23  \w     92.00 117.00   0.50    3.00    --   54.00  76.00  18.96   50
 24  \w     37.00  72.00   0.50    3.00    --   54.00  72.00 158.42   70
 25  \w     38.00  64.00   0.50    3.00    --   54.00  73.00 -26.94   52
 26  \w     43.00  88.00   0.50    3.00    --   58.00  71.00  89.63   90
 27  \w     88.00 125.00   0.50    3.00    --   58.00  52.00-127.77   74
 28  \w     48.00  73.00   0.50    3.00    --   58.00  52.00-127.77   50
 29  \w     41.00  74.00   0.50    3.00    --   58.00  73.00  43.65   66
 30  \w     47.00  86.00   0.50    3.00    --   62.00  69.00  -8.71   78
 31  \w     47.00 116.00   0.50    3.00    --   62.00  66.00 -61.01  138
 32  \w     49.00  75.00   0.50    3.00    --   66.00  74.00-110.66   52
 33  \w     96.00 129.00   0.50    3.00    --   66.00  74.00-110.66   66
 34  \w     54.00  88.00   0.50    3.00    --   70.00  72.00 132.92   68
 35  \w     95.00 132.00   0.50    3.00    --   70.00  72.00 132.92   74
 36  \w     63.00 143.00   0.50   12.00    --   82.00  77.00 -24.55  160
 37  \w     71.00 114.00   0.50   12.00    --   86.00  66.00  73.83   86
 38  \w    122.00 152.00   0.50   12.00    --   86.00  66.00  73.83   60
 39  \w     89.00 114.00   0.50   12.00    --  102.88  77.00 120.00   50
 40  \w     99.00 170.00   0.50   12.00    --  102.88  38.00-150.00  142
 41  \w     98.00 155.00   0.50   12.00    --  102.88  57.00  30.00  114
 42  \w     82.00 112.00   0.50   12.00    --  102.88 -77.00  90.00   60
 43  \w     47.00  76.00   0.50   12.00    --  102.88 -77.00  90.00   58
 44  \w     96.00 136.00   0.50   12.00    --  102.88  38.00 150.00   80
 45  \w     85.00 136.00   0.50   12.00    --  102.88  77.00 150.00  102
 46  \w     91.00 152.00   0.50   12.00    --  102.88  57.00  90.00  122
 47  \w    137.00 169.00   0.50   12.00    --  102.88  38.00 -60.00   64
 48  \w     97.00 134.00   0.50   12.00    --  102.88  57.00-120.00   74
 49  \w     87.00 146.00   0.50   12.00    --  102.88  77.00-120.00  118
 50  \w     98.00 145.00   0.50   12.00    --  102.88  38.00 -30.00   94
 51  \w     96.00 123.00   0.50   12.00    --  102.88  38.00 -60.00   54
 52  \w     83.00 109.00   0.50   12.00    --  102.88  77.00-150.00   52
 53  \w     78.00 108.00   0.50   12.00    --  102.88-125.00 -30.00   60
 54  \w     83.00 114.00   0.50   12.00    --  102.88 -57.00 -90.00   62
 55  \w     40.00  65.00   0.50   12.00    --  102.88-125.00 -30.00   50
 56  \w     91.00 140.00   0.50   12.00    --  102.88  57.00  60.00   98
 57  \w     40.00  78.00   0.50   12.00    --  102.88 -57.00 -90.00   76
 58  \w     93.00 119.00   0.50   12.00    --  102.88  57.00 150.00   52
 59  \w     91.00 118.00   0.50   12.00    --  102.88  57.00 -60.00   54
 60  \w     44.00  92.00   0.50   12.00    --  102.88 -77.00  30.00   96
 61  \w    114.00 139.00   0.50   12.00    --  102.88  77.00   0.00   50
 62  \w     84.00 110.00   0.50   12.00    --  102.88  77.00   0.00   52
 63  \w     98.00 125.00   0.50   12.00    --  102.88  57.00-180.00   54
 64  \w     74.00 130.00   0.50   12.00    --  108.01 -20.00  19.43  112
 65  \w     38.00  70.00   0.50   12.00    --  108.01 -20.00  19.43   64
 66  \w     48.00 115.00   0.50   12.00    --  108.01 -50.00 119.76  134
 67  \w     76.00 105.00   0.50   12.00    --  108.01 -99.00-143.33   58
 68  \w     38.00 109.00   0.50   12.00    --  108.01 -49.00 -71.32  142
 69  \w     39.00  97.00   0.50   12.00    --  108.01 -58.00-139.98  116
 70  \w     44.00 114.00   0.50   12.00    --  108.01 -70.00  51.57  140
;
_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      -0.1405342000
_diffrn_orient_matrix_UB_12      -0.1019558000
_diffrn_orient_matrix_UB_13      -0.1944247000
_diffrn_orient_matrix_UB_21      0.2091618000
_diffrn_orient_matrix_UB_22      0.0134854000
_diffrn_orient_matrix_UB_23      -0.0781700000
_diffrn_orient_matrix_UB_31      0.0395162000
_diffrn_orient_matrix_UB_32      -0.1970611000
_diffrn_orient_matrix_UB_33      0.0096924000
_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  0.0273
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5047
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.227
_diffrn_reflns_theta_min         7.023
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.948
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.196
_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    1.512
_exptl_crystal_description       needle
_exptl_crystal_F_000             156
_exptl_crystal_preparation       '1:1 molar ratio (1/100 mole)'
_exptl_crystal_recrystallization_method 'Grown in 0.2 mm capillary'
_exptl_crystal_size_max          0.912
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.203
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1349
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0657
_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^)+(0.0880P)^2^+0.1208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1160
_reflns_number_total             1349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00989h2.cif
_cod_data_source_block           exp_102
_cod_database_code               7251327
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C8 H10 C6 F5 Cl'
_chemical_oxdiff_usercomment     '0.2mm capillary '
_shelx_estimated_absorpt_t_max   0.586
_shelx_estimated_absorpt_t_min   0.174
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Shared sites
{F1, Cl1}
3. Restrained distances
 H7a-H7b \\sim H7b-H7c \\sim H7c-H7d \\sim H7d-H7e \\sim H7e-H7f \\sim H7f-H7a
 with sigma of 0.01
 C7-H7a \\sim C7-H7e \\sim C7-H7b \\sim C7-H7f \\sim C7-H7c \\sim C7-H7d \\sim
C4-H4 \\sim C5-H5
 with sigma of 0.01
 C6-H7a \\sim C6-H7e \\sim C6-H7b \\sim C6-H7f \\sim C6-H7c \\sim C6-H7d
 with sigma of 0.01
 C4-H5 \\sim C6-H5
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
5. Others
 Fixed Sof: Cl1(0.5) F1(0.5) H7a(0.5) H7b(0.5) H7c(0.5) H7d(0.5) H7e(0.5)
 H7f(0.5)
;
_shelx_res_checksum              65021
_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 2.480
_oxdiff_exptl_absorpt_empirical_full_min 0.540