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_7251325
_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                89.116(4)
_cell_angle_beta                 102.483(5)
_cell_angle_gamma                94.488(5)
_cell_formula_units_Z            2
_cell_length_a                   6.5505(4)
_cell_length_b                   7.3190(4)
_cell_length_c                   14.6880(8)
_cell_measurement_reflns_used    4754
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.3420
_cell_measurement_theta_min      6.0830
_cell_volume                     685.43(7)
_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      200
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.965
_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     -4.00  21.00   1.00    1.00    --   34.00  92.00 -78.29   25
  2  \w     -4.00  21.00   1.00    1.00    --   34.00  92.00 142.09   25
  3  \w      3.00  28.00   1.00    1.00    --   38.00  86.00  71.42   25
  4  \w    -65.00  32.00   1.00    1.00    --  -42.62  38.00-150.00   97
  5  \w   -108.00 -23.00   1.00    1.00    --  -42.62 -38.00  30.00   85
  6  \w   -115.00 -19.00   1.00    1.00    --  -42.62 -38.00 120.00   96
  7  \w   -118.00 -16.00   1.00    1.00    --  -42.62 -19.00-150.00  102
  8  \w     27.00  99.00   1.00    1.00    --   42.62-125.00   0.00   72
  9  \w      7.00  74.00   1.00    1.00    --   42.62 -99.00  60.00   67
 10  \w     13.00  38.00   1.00    1.00    --   46.00  77.00-132.25   25
 11  \w     16.00  41.00   1.00    1.00    --   50.00  82.00 -70.10   25
 12  \w     16.00  41.00   1.00    1.00    --   50.00  82.00-111.25   25
 13  \w     16.00  41.00   1.00    1.00    --   50.00  82.00 151.52   25
 14  \w     16.00  41.00   1.00    1.00    --   50.00  82.00  78.82   25
 15  \w     16.00  42.00   1.00    1.00    --   50.00  81.00 -10.61   26
 16  \w     31.00  58.00   1.00    1.00    --   62.00  71.00 166.29   27
 17  \w     32.00  58.00   1.00    1.00    --   62.00  71.00  -6.83   26
 18  \w    108.00 135.00   1.00    1.00    --   66.00  67.00  83.35   27
 19  \w     36.00  63.00   1.00    1.00    --   66.00  67.00  83.35   27
 20  \w     35.00  61.00   1.00    1.00    --   66.00  69.00 -43.92   26
 21  \w     40.00  67.00   1.00    1.00    --   70.00  70.00-152.86   27
 22  \w     39.00  72.00   1.00    1.00    --   70.00  69.00  29.45   33
 23  \w     40.00  66.00   1.00    1.00    --   70.00  66.00 -87.07   26
 24  \w     96.00 123.00   1.00    1.00    --   74.00  68.00-178.21   27
 25  \w     44.00  72.00   1.00    1.00    --   74.00  68.00-178.21   28
 26  \w     47.00  73.00   1.00    3.25    --   78.00  71.00  87.34   26
 27  \w     49.00  75.00   1.00    3.25    --   78.00  59.00  -0.86   26
 28  \w     52.00  89.00   1.00    3.25    --   82.00  66.00 127.19   37
 29  \w     51.00  79.00   1.00    3.25    --   82.00  70.00 -70.37   28
 30  \w     52.00  77.00   1.00    3.25    --   82.00  70.00-110.40   25
 31  \w     59.00  85.00   1.00    3.25    --   90.00  70.00-148.22   26
 32  \w     64.00 101.00   1.00    3.25    --   94.00  68.00  91.73   37
 33  \w     64.00 154.00   1.00    3.25    --   94.00  64.00  56.30   90
 34  \w    123.00 155.00   1.00    3.25    --   94.00  63.00   8.24   32
 35  \w     66.00  94.00   1.00    3.25    --   94.00  63.00   8.24   28
 36  \w    105.00 167.00   1.00    3.25    --   94.00  68.00  91.73   62
 37  \w     77.00 105.00   1.00    3.25    --  106.06  61.00 -90.00   28
 38  \w    105.00 131.00   1.00    3.25    --  106.06 -45.00 -60.00   26
 39  \w     34.00  89.00   1.00    3.25    --  106.06 -45.00 -60.00   55
 40  \w     48.00  75.00   1.00    3.25    --  106.06 -45.00-150.00   27
 41  \w     85.00 111.00   1.00    3.25    --  106.06-125.00-180.00   26
 42  \w     77.00 160.00   1.00    3.25    --  106.06  61.00 -60.00   83
 43  \w     77.00 178.00   1.00    3.25    --  106.06  61.00 -30.00  101
 44  \w     77.00 178.00   1.00    3.25    --  106.06  61.00-180.00  101
 45  \w     54.00 107.00   1.00    3.25    --  106.06 -94.00  30.00   53
 46  \w     77.00 177.00   1.00    3.25    --  106.06  61.00-120.00  100
 47  \w     77.00 156.00   1.00    3.25    --  106.06  61.00 150.00   79
 48  \w     77.00 175.00   1.00    3.25    --  106.06  61.00  30.00   98
 49  \w     26.00 107.00   1.00    3.25    --  106.06 -99.00 -47.36   81
 50  \w     45.00 112.00   1.00    3.25    --  106.06-125.00 -90.00   67
 51  \w    114.00 152.00   1.00    3.25    --  106.06  61.00-150.00   38
 52  \w     78.00 104.00   1.00    3.25    --  106.06  61.00-150.00   26
 53  \w    104.00 130.00   1.00    3.25    --  106.06 -45.00-150.00   26
 54  \w     38.00 132.00   1.00    3.25    --  106.06 -61.00  60.00   94
 55  \w    124.00 164.00   1.00    3.25    --  106.06  61.00 120.00   40
 56  \w     77.00 118.00   1.00    3.25    --  106.06  61.00 120.00   41
 57  \w    127.00 166.00   1.00    3.25    --  106.06  61.00 -90.00   39
;
_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      0.0967886409
_diffrn_orient_matrix_UB_12      0.0386110535
_diffrn_orient_matrix_UB_13      -0.0857253839
_diffrn_orient_matrix_UB_21      -0.2203743666
_diffrn_orient_matrix_UB_22      -0.0202918114
_diffrn_orient_matrix_UB_23      -0.0639790519
_diffrn_orient_matrix_UB_31      -0.0207893107
_diffrn_orient_matrix_UB_32      0.2065816859
_diffrn_orient_matrix_UB_33      0.0099047740
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11428
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.531
_diffrn_reflns_theta_min         6.065
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.916
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
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    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_preparation       '50:50 molar mixture of components'
_exptl_crystal_recrystallization_method
'Crystal grown in situ from the melt in a 0.3mm X-ray capillary'
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     280
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0761
_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^)+(0.1151P)^2^+0.3650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2145
_refine_ls_wR_factor_ref         0.2352
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1969
_reflns_number_total             2667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00989h2.cif
_cod_data_source_block           exp_2920
_cod_database_code               7251325
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C6 F5 Cl C8 H10'
_chemical_oxdiff_usercomment     '0.3mm capillary'
_shelx_estimated_absorpt_t_max   0.771
_shelx_estimated_absorpt_t_min   0.373
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
2. Shared sites
{F1, Cl1}
{F4, Cl4}
3. Restrained distances
 C13-H13A \\sim C13-H13B \\sim C13-H13C \\sim C13-H13D \\sim C13-H13E \\sim
C13-H13F \\sim C14-H14A ~
 C14-H14B \\sim C14-H14C \\sim C14-H14D \\sim C14-H14E \\sim C14-H14F \\sim
C8-H8 \\sim C9-H9 \\sim C11-H11
 \\sim C12-H12
 with sigma of 0.01
 H13A-H13F \\sim H13F-H13B \\sim H13B-H13D \\sim H13D-H13C \\sim H13C-H13E
\\sim H13E-H13A \\sim H14A-
 H14F \\sim H14F-H14B \\sim H14B-H14D \\sim H14D-H14C \\sim H14C-H14E \\sim
H14E-H14A
 with sigma of 0.01
 C7-H13A \\sim C7-H13B \\sim C7-H13C \\sim C7-H13D \\sim C7-H13E \\sim C7-H13F
\\sim C10-H14A \\sim C10-
 H14B \\sim C10-H14C \\sim C10-H14D \\sim C10-H14E \\sim C10-H14F
 with sigma of 0.01
 C7-H8 \\sim C9-H8 \\sim C8-H9 \\sim C10-H9 \\sim C10-H11 \\sim C12-H11 \\sim
C11-H12 \\sim C7-H12
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
Uanis(F4) = Uanis(Cl4)
5. Others
 Sof(Cl1)=Sof(F4)=1-FVAR(1)
 Sof(F1)=Sof(Cl4)=FVAR(1)
 Fixed Sof: H13A(0.5) H13B(0.5) H13C(0.5) H13D(0.5) H13E(0.5) H13F(0.5)
 H14A(0.5) H14B(0.5) H14C(0.5) H14D(0.5) H14E(0.5) H14F(0.5)
;
_shelx_res_checksum              24462
_olex2_date_sample_data_collection 2021-09-30
_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 14.431
_oxdiff_exptl_absorpt_empirical_full_min 0.318