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_7251331
_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   mixed
_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                111.378(8)
_cell_angle_beta                 99.662(7)
_cell_angle_gamma                95.159(7)
_cell_formula_units_Z            1
_cell_length_a                   6.1383(5)
_cell_length_b                   7.4411(7)
_cell_length_c                   7.9224(6)
_cell_measurement_reflns_used    2170
_cell_measurement_temperature    120
_cell_measurement_theta_max      72.6160
_cell_measurement_theta_min      6.1170
_cell_volume                     327.65(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_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      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.962
_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      3.00  28.00   1.00    1.00    --   38.00  85.00 -88.50   25
  2  \w   -103.00 -76.00   1.00    1.00    --  -40.87 -38.00-120.00   27
  3  \w    -43.00 -18.00   1.00    1.00    --  -40.87 -38.00-120.00   25
  4  \w    -87.00 -14.00   1.00    1.00    --  -40.87 125.00  30.00   73
  5  \w    -81.00 -48.00   1.00    1.00    --  -40.87 -38.00  30.00   33
  6  \w    -84.00 -10.00   1.00    1.00    --  -40.87 125.00-150.00   74
  7  \w    -41.00 -16.00   1.00    1.00    --  -40.87 -38.00  30.00   25
  8  \w     14.00  39.00   1.00    1.00    --   46.00  76.00 117.96   25
  9  \w     15.00  40.00   1.00    1.00    --   46.00  79.00 -59.03   25
 10  \w     13.00  40.00   1.00    1.00    --   46.00  78.00  71.30   27
 11  \w     16.00  41.00   1.00    1.00    --   50.00  81.00 156.44   25
 12  \w     16.00  41.00   1.00    1.00    --   50.00  82.00   2.50   25
 13  \w     28.00  60.00   1.00    1.00    --   54.00  54.00 120.47   32
 14  \w     99.00 127.00   1.00    1.00    --   54.00  69.00-176.46   28
 15  \w     79.00 115.00   1.00    1.00    --   54.00  68.00 -85.66   36
 16  \w     76.00 101.00   1.00    1.00    --   54.00  54.00 120.47   25
 17  \w     31.00  59.00   1.00    1.00    --   54.00  69.00-176.46   28
 18  \w     26.00  76.00   1.00    1.00    --   54.00  68.00 -85.66   50
 19  \w     31.00  78.00   1.00    1.00    --   62.00  70.00-143.17   47
 20  \w     42.00  69.00   1.00    1.00    --   62.00  60.00 117.98   27
 21  \w     91.00 118.00   1.00    1.00    --   62.00  60.00 117.98   27
 22  \w     38.00  97.00   1.00    1.00    --   66.00  55.00  41.86   59
 23  \w     95.00 141.00   1.00    1.00    --   70.00  67.00 133.64   46
 24  \w     40.00  89.00   1.00    1.00    --   70.00  67.00 133.64   49
 25  \w     98.00 143.00   1.00    1.00    --   70.00  68.00 -44.39   45
 26  \w     40.00  68.00   1.00    1.00    --   70.00  68.00 -44.39   28
 27  \w     54.00  90.00   1.00    1.00    --   74.00  62.00 -21.12   36
 28  \w     52.00  79.00   1.00    1.00    --   82.00  69.00-151.83   27
 29  \w     77.00 132.00   1.00    1.00    --  106.06 -77.00 -30.00   55
 30  \w     33.00  60.00   1.00    1.00    --  106.06 -77.00 -30.00   27
 31  \w     77.00 107.00   1.00    1.00    --  106.06  61.00  30.00   30
 32  \w     79.00 122.00   1.00    1.00    --  106.06  61.00 -60.00   43
 33  \w     80.00 177.00   1.00    1.00    --  106.06  61.00 150.00   97
 34  \w     80.00 107.00   1.00    1.00    --  106.06  45.00 -60.00   27
 35  \w     77.00 176.00   1.00    1.00    --  106.06  61.00-120.00   99
 36  \w    137.00 178.00   1.00    1.00    --  106.06  61.00  90.00   41
 37  \w    122.00 168.00   1.00    1.00    --  106.06  77.00-180.00   46
 38  \w     99.00 163.00   1.00    1.00    --  106.06 125.00 -60.00   64
 39  \w     31.00 136.00   1.00    1.00    --  106.06 -77.00-120.00  105
 40  \w     84.00 117.00   1.00    1.00    --  106.06  61.00 -30.00   33
 41  \w    116.00 141.00   1.00    1.00    --  106.06  61.00-150.00   25
 42  \w     40.00 130.00   1.00    1.00    --  106.06-149.00-165.00   90
 43  \w     82.00 113.00   1.00    1.00    --  106.06  61.00-150.00   31
 44  \w    112.00 177.00   1.00    1.00    --  106.06  61.00  60.00   65
 45  \w    111.00 177.00   1.00    1.00    --  106.06  55.00   0.57   66
 46  \w     78.00 114.00   1.00    1.00    --  106.06  61.00  90.00   36
 47  \w     80.00 111.00   1.00    1.00    --  106.06  61.00  60.00   31
 48  \w     78.00 110.00   1.00    1.00    --  106.06  55.00   0.57   32
 49  \w     81.00 117.00   1.00    1.00    --  106.06  61.00 120.00   36
 50  \w     61.00 111.00   1.00    1.00    --  106.06-125.00-120.00   50
;
_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      0.1060434000
_diffrn_orient_matrix_UB_12      -0.0265104000
_diffrn_orient_matrix_UB_13      -0.1687705000
_diffrn_orient_matrix_UB_21      -0.2335239000
_diffrn_orient_matrix_UB_22      -0.0790590000
_diffrn_orient_matrix_UB_23      -0.1300813000
_diffrn_orient_matrix_UB_31      -0.0290067000
_diffrn_orient_matrix_UB_32      0.2094163000
_diffrn_orient_matrix_UB_33      0.0185401000
_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  0.0489
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.561
_diffrn_reflns_theta_min         6.144
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.051
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
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    1.564
_exptl_crystal_description       plank
_exptl_crystal_F_000             156
_exptl_crystal_recrystallization_method
'Crystallized in situ in 0.3mm X-ray capillary'
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1281
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0910P)^2^+0.1738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1588
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1085
_reflns_number_total             1281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00989h2.cif
_cod_data_source_block           exp_2922
_cod_database_code               7251331
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C6 F5 Cl C8 H10'
_chemical_oxdiff_usercomment     '0.3mm capillary'
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{Cl1, F1}
3. Restrained distances
 C1-C2 \\sim C2-C3
 with sigma of 0.01
 C2-F2 \\sim C3-F3
 with sigma of 0.01
4. Restrained planarity
 Cl1, F2, F3, C1, C2, C3
 with sigma of 0.05
5. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(F1)
6. Others
 Fixed Sof: Cl1(0.5) F1(0.5)
7.a Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              71946
_olex2_date_sample_data_collection 2021-09-30
_olex2_exptl_crystal_mounting_method 'Sealed capillary glued in a brass pip'
_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 12.023
_oxdiff_exptl_absorpt_empirical_full_min 0.280