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_7251326
_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
'1,4-dichlorotetrafluorobenzene 1,4-dimethylbenzene'
_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             2022-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.380(4)
_cell_angle_beta                 100.429(5)
_cell_angle_gamma                94.132(5)
_cell_formula_units_Z            2
_cell_length_a                   6.4620(4)
_cell_length_b                   7.4574(4)
_cell_length_c                   15.1315(7)
_cell_measurement_reflns_used    4544
_cell_measurement_temperature    240
_cell_measurement_theta_max      72.5060
_cell_measurement_theta_min      5.9130
_cell_volume                     715.13(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240
_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 0.969
_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    2.50    --   34.00  91.00 -44.79   25
  2  \w      7.00  32.00   1.00    2.50    --   42.00  84.00  84.25   25
  3  \w   -117.00 -60.00   1.00    2.50    --  -42.87 -38.00-120.00   57
  4  \w    -57.00 -23.00   1.00    2.50    --  -42.87 -38.00-120.00   34
  5  \w    -68.00  31.00   1.00    2.50    --  -42.87  77.00-180.00   99
  6  \w   -115.00 -24.00   1.00    2.50    --  -42.87 -38.00 120.00   91
  7  \w     15.00  42.00   1.00    2.50    --   42.87  57.00-120.00   27
  8  \w     28.00  93.00   1.00    2.50    --   42.87-125.00  30.00   65
  9  \w     10.00  36.00   1.00    2.50    --   42.87  77.00  32.79   26
 10  \w     17.00  42.00   1.00    2.50    --   50.00  81.00-156.83   25
 11  \w     16.00  41.00   1.00    2.50    --   50.00  82.00  -2.18   25
 12  \w     16.00  42.00   1.00    2.50    --   50.00  82.00 107.97   26
 13  \w     16.00  41.00   1.00    2.50    --   50.00  81.00 -94.85   25
 14  \w     16.00  41.00   1.00    2.50    --   50.00  82.00 -46.38   25
 15  \w     37.00  82.00   1.00    2.50    --   62.00  53.00  53.92   45
 16  \w     35.00  64.00   1.00    2.50    --   66.00  69.00-171.29   29
 17  \w     41.00  79.00   1.00    2.50    --   66.00  51.00 -61.76   38
 18  \w    110.00 137.00   1.00    2.50    --   70.00  69.00 141.78   27
 19  \w     40.00  69.00   1.00    2.50    --   70.00  69.00 141.78   29
 20  \w     43.00  90.00   1.00    2.50    --   74.00  69.00 -26.90   47
 21  \w     47.00  81.00   1.00    2.50    --   74.00  62.00 118.72   34
 22  \w     50.00 103.00   1.00   10.00    --   78.00  67.00  52.69   53
 23  \w     47.00 105.00   1.00   10.00    --   78.00  70.00-147.55   58
 24  \w     55.00  82.00   1.00   10.00    --   82.00  60.00 128.19   27
 25  \w    121.00 157.00   1.00   10.00    --   86.00  66.00  27.75   36
 26  \w     59.00  97.00   1.00   10.00    --   86.00  66.00  27.75   38
 27  \w     61.00  93.00   1.00   10.00    --   90.00  60.00 -52.01   32
 28  \w    127.00 163.00   1.00   10.00    --   90.00  68.00-155.19   36
 29  \w     68.00  94.00   1.00   10.00    --   90.00  68.00-155.19   26
 30  \w     61.00  87.00   1.00   10.00    --   90.00  60.00 -79.19   26
 31  \w     77.00 178.00   1.00   10.00    --  106.06  61.00 120.00  101
 32  \w     80.00 164.00   1.00   10.00    --  106.06  61.00-120.00   84
 33  \w     34.00  72.00   1.00   10.00    --  106.06 -61.00  30.00   38
 34  \w    121.00 174.00   1.00   10.00    --  106.06  45.00   0.00   53
 35  \w     81.00 119.00   1.00   10.00    --  106.06  45.00   0.00   38
 36  \w     91.00 129.00   1.00   10.00    --  106.06 -61.00-150.00   38
 37  \w    146.00 173.00   1.00   10.00    --  106.06  61.00  60.00   27
 38  \w     34.00 106.00   1.00   10.00    --  106.06-125.00 150.00   72
 39  \w     78.00 103.00   1.00   10.00    --  106.06  61.00  60.00   25
 40  \w     24.00 106.00   1.00   10.00    --  106.06 -94.00-150.00   82
 41  \w     69.00 100.00   1.00   10.00    --  106.06 -94.00 150.00   31
 42  \w     41.00 112.00   1.00   10.00    --  106.06-125.00  60.00   71
 43  \w     23.00  68.00   1.00   10.00    --  106.06 -94.00 150.00   45
 44  \w     35.00 107.00   1.00   10.00    --  106.06 -94.00 -90.00   72
 45  \w     84.00 139.00   1.00   10.00    --  106.06  45.00  30.00   55
 46  \w    150.00 177.00   1.00   10.00    --  106.06  45.00  30.00   27
 47  \w    109.00 134.00   1.00   10.00    --  106.06  61.00 150.00   25
 48  \w     78.00 103.00   1.00   10.00    --  106.06  61.00 150.00   25
 49  \w     77.00 162.00   1.00   10.00    --  106.06  61.00-180.00   85
 50  \w     77.00 174.00   1.00   10.00    --  106.06  61.00  76.54   97
 51  \w     77.00 171.00   1.00   10.00    --  106.06  61.00 -60.00   94
;
_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      0.1100121000
_diffrn_orient_matrix_UB_12      0.1361241000
_diffrn_orient_matrix_UB_13      -0.0557953000
_diffrn_orient_matrix_UB_21      0.1118267000
_diffrn_orient_matrix_UB_22      0.0994939000
_diffrn_orient_matrix_UB_23      0.0870630000
_diffrn_orient_matrix_UB_31      0.1856925000
_diffrn_orient_matrix_UB_32      -0.1203613000
_diffrn_orient_matrix_UB_33      0.0052908000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.969
_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       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10480
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.271
_diffrn_reflns_theta_min         5.948
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.401
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.387
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.510
_exptl_crystal_description       plank
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method
'Grown from the melt in 0.3mm X-ray capillary'
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0569
_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^)+(0.0939P)^2^+0.1444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1788
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1903
_reflns_number_total             2776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00989h2.cif
_cod_data_source_block           exp_2971
_cod_database_code               7251326
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C6 F4 Cl2 C8 H10'
_chemical_oxdiff_usercomment
'Repeat experiment no. 3 - same 0.3mm capillary - melt is around 280K'
_shelx_estimated_absorpt_t_max   0.720
_shelx_estimated_absorpt_t_min   0.341
_reflns_odcompleteness_completeness 99.69
_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,H,H,H) groups
2. Restrained distances
 C13-H13A \\sim C13-H13E \\sim C13-H13B \\sim C13-H13F \\sim C13-H13C \\sim
C13-H13D
 with sigma of 0.01
 C7-H13A \\sim C7-H13E \\sim C7-H13B \\sim C7-H13F \\sim C7-H13C \\sim C7-H13D
 with sigma of 0.01
 H13A-H13F \\sim H13F-H13B \\sim H13B-H13D \\sim H13D-H13C \\sim H13C-H13E
\\sim H13E-H13A
 with sigma of 0.01
 C14-H14A \\sim C14-H14F \\sim C14-H14B \\sim C14-H14D \\sim C14-H14C \\sim
C14-H14E
 with sigma of 0.01
 C10-H14A \\sim C10-H14F \\sim C10-H14B \\sim C10-H14D \\sim C10-H14C \\sim
C10-H14E
 with sigma of 0.01
 H14A-H14F \\sim H14F-H14B \\sim H14B-H14D \\sim H14D-H14C \\sim H14C-H14E
\\sim H14E-H14A
 with sigma of 0.01
3. Others
 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              99389
_olex2_date_sample_data_collection 2021-10-27
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 8.201
_oxdiff_exptl_absorpt_empirical_full_min 0.383