#------------------------------------------------------------------------------
#$Date: 2025-11-27 00:50:05 +0100 (Thu 27 de Nov de 2025) $
#$Revision: 303448 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/13/7251331.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7251331
loop_
_publ_author_name
'Bear, Joseph C.'
'Cockcroft, Jeremy Karl'
'Rosu-Finsen, Alexander'
'Williams, Jeffrey Huw'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  28.00   1.00    1.00    --   38.00  85.00 -88.50   25
  2  ω   -103.00 -76.00   1.00    1.00    --  -40.87 -38.00-120.00   27
  3  ω    -43.00 -18.00   1.00    1.00    --  -40.87 -38.00-120.00   25
  4  ω    -87.00 -14.00   1.00    1.00    --  -40.87 125.00  30.00   73
  5  ω    -81.00 -48.00   1.00    1.00    --  -40.87 -38.00  30.00   33
  6  ω    -84.00 -10.00   1.00    1.00    --  -40.87 125.00-150.00   74
  7  ω    -41.00 -16.00   1.00    1.00    --  -40.87 -38.00  30.00   25
  8  ω     14.00  39.00   1.00    1.00    --   46.00  76.00 117.96   25
  9  ω     15.00  40.00   1.00    1.00    --   46.00  79.00 -59.03   25
 10  ω     13.00  40.00   1.00    1.00    --   46.00  78.00  71.30   27
 11  ω     16.00  41.00   1.00    1.00    --   50.00  81.00 156.44   25
 12  ω     16.00  41.00   1.00    1.00    --   50.00  82.00   2.50   25
 13  ω     28.00  60.00   1.00    1.00    --   54.00  54.00 120.47   32
 14  ω     99.00 127.00   1.00    1.00    --   54.00  69.00-176.46   28
 15  ω     79.00 115.00   1.00    1.00    --   54.00  68.00 -85.66   36
 16  ω     76.00 101.00   1.00    1.00    --   54.00  54.00 120.47   25
 17  ω     31.00  59.00   1.00    1.00    --   54.00  69.00-176.46   28
 18  ω     26.00  76.00   1.00    1.00    --   54.00  68.00 -85.66   50
 19  ω     31.00  78.00   1.00    1.00    --   62.00  70.00-143.17   47
 20  ω     42.00  69.00   1.00    1.00    --   62.00  60.00 117.98   27
 21  ω     91.00 118.00   1.00    1.00    --   62.00  60.00 117.98   27
 22  ω     38.00  97.00   1.00    1.00    --   66.00  55.00  41.86   59
 23  ω     95.00 141.00   1.00    1.00    --   70.00  67.00 133.64   46
 24  ω     40.00  89.00   1.00    1.00    --   70.00  67.00 133.64   49
 25  ω     98.00 143.00   1.00    1.00    --   70.00  68.00 -44.39   45
 26  ω     40.00  68.00   1.00    1.00    --   70.00  68.00 -44.39   28
 27  ω     54.00  90.00   1.00    1.00    --   74.00  62.00 -21.12   36
 28  ω     52.00  79.00   1.00    1.00    --   82.00  69.00-151.83   27
 29  ω     77.00 132.00   1.00    1.00    --  106.06 -77.00 -30.00   55
 30  ω     33.00  60.00   1.00    1.00    --  106.06 -77.00 -30.00   27
 31  ω     77.00 107.00   1.00    1.00    --  106.06  61.00  30.00   30
 32  ω     79.00 122.00   1.00    1.00    --  106.06  61.00 -60.00   43
 33  ω     80.00 177.00   1.00    1.00    --  106.06  61.00 150.00   97
 34  ω     80.00 107.00   1.00    1.00    --  106.06  45.00 -60.00   27
 35  ω     77.00 176.00   1.00    1.00    --  106.06  61.00-120.00   99
 36  ω    137.00 178.00   1.00    1.00    --  106.06  61.00  90.00   41
 37  ω    122.00 168.00   1.00    1.00    --  106.06  77.00-180.00   46
 38  ω     99.00 163.00   1.00    1.00    --  106.06 125.00 -60.00   64
 39  ω     31.00 136.00   1.00    1.00    --  106.06 -77.00-120.00  105
 40  ω     84.00 117.00   1.00    1.00    --  106.06  61.00 -30.00   33
 41  ω    116.00 141.00   1.00    1.00    --  106.06  61.00-150.00   25
 42  ω     40.00 130.00   1.00    1.00    --  106.06-149.00-165.00   90
 43  ω     82.00 113.00   1.00    1.00    --  106.06  61.00-150.00   31
 44  ω    112.00 177.00   1.00    1.00    --  106.06  61.00  60.00   65
 45  ω    111.00 177.00   1.00    1.00    --  106.06  55.00   0.57   66
 46  ω     78.00 114.00   1.00    1.00    --  106.06  61.00  90.00   36
 47  ω     80.00 111.00   1.00    1.00    --  106.06  61.00  60.00   31
 48  ω     78.00 110.00   1.00    1.00    --  106.06  55.00   0.57   32
 49  ω     81.00 117.00   1.00    1.00    --  106.06  61.00 120.00   36
 50  ω     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       'ω 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/[σ²(Fo²)+(0.0910P)²+0.1738P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.20087(15) 0.10012(14) 0.39441(12) 0.0445(3) Uani 0.5 1 d . . P A 1
F1 F 0.20087(15) 0.10012(14) 0.39441(12) 0.0445(3) Uani 0.5 1 d . . P A 1
F2 F 0.4341(2) 0.1778(2) 0.1417(2) 0.0451(5) Uani 1 1 d D . . A 1
F3 F 0.2533(2) 0.0838(2) -0.2204(2) 0.0445(5) Uani 1 1 d D . . A 1
C1 C 0.0941(4) 0.0474(3) 0.1860(3) 0.0350(6) Uani 1 1 d D . . A 1
C2 C 0.2197(4) 0.0891(3) 0.0720(3) 0.0356(6) Uani 1 1 d D . . A 1
C3 C 0.1278(4) 0.0420(3) -0.1122(3) 0.0352(6) Uani 1 1 d D . . A 1
C5 C 0.1131(4) 0.5224(4) -0.1288(4) 0.0376(6) Uani 1 1 d . . . B 2
H5 H 0.193(6) 0.531(5) -0.222(5) 0.060(10) Uiso 1 1 d . . . C 2
C6 C 0.2240(4) 0.5768(4) 0.0532(4) 0.0365(6) Uani 1 1 d . . . B 2
H6 H 0.383(6) 0.641(5) 0.099(5) 0.056(9) Uiso 1 1 d . . . D 2
C7 C 0.1144(4) 0.5555(4) 0.1860(3) 0.0364(6) Uani 1 1 d . . . B 2
C8 C 0.2362(7) 0.6136(6) 0.3848(4) 0.0642(10) Uani 1 1 d . . . B 2
H8A H 0.2991 0.5023 0.3993 0.096 Uiso 1 1 calc R U . B 2
H8B H 0.1312 0.6529 0.4670 0.096 Uiso 1 1 calc R U . B 2
H8C H 0.3575 0.7234 0.4174 0.096 Uiso 1 1 calc R U . B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 1 -3 0.0328
-3 -1 3 0.0706
1 -5 1 0.1936
2 3 1 0.1075
1 3 -5 0.0308
1 1 -5 0.0262
-1 3 2 0.0884
-1 -1 5 0.0820
4 1 -2 0.0443
-3 2 2 0.0818
-1 1 -4 0.0527
-1 0 -4 0.0525
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Cl1 120.2(2) . . ?
C2 C1 C3 119.0(2) . 2 ?
C3 C1 Cl1 120.8(2) 2 . ?
F2 C2 C1 119.8(2) . . ?
F2 C2 C3 119.5(2) . . ?
C3 C2 C1 120.7(2) . . ?
F3 C3 C1 120.1(2) . 2 ?
F3 C3 C2 119.6(2) . . ?
C2 C3 C1 120.3(2) . 2 ?
C6 C5 H5 121(2) . . ?
C6 C5 C7 121.0(2) . 2_565 ?
C7 C5 H5 118(2) 2_565 . ?
C5 C6 H6 122(2) . . ?
C5 C6 C7 121.5(2) . . ?
C7 C6 H6 116(2) . . ?
C5 C7 C8 121.0(3) 2_565 . ?
C6 C7 C5 117.5(2) . 2_565 ?
C6 C7 C8 121.5(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.558(3) . ?
F2 C2 1.344(3) . ?
F3 C3 1.340(3) . ?
C1 C2 1.379(3) . ?
C1 C3 1.388(3) 2 ?
C2 C3 1.373(4) . ?
C3 C1 1.388(3) 2 ?
C5 H5 0.97(4) . ?
C5 C6 1.379(4) . ?
C5 C7 1.394(4) 2_565 ?
C6 H6 0.99(4) . ?
C6 C7 1.387(4) . ?
C7 C5 1.394(4) 2_565 ?
C7 C8 1.509(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 F2 -0.8(3) . . . . ?
Cl1 C1 C2 C3 179.50(19) . . . . ?
F2 C2 C3 F3 0.4(3) . . . . ?
F2 C2 C3 C1 -179.2(2) . . . 2 ?
C1 C2 C3 F3 -179.9(2) . . . . ?
C1 C2 C3 C1 0.5(4) . . . 2 ?
C3 C1 C2 F2 179.2(2) 2 . . . ?
C3 C1 C2 C3 -0.5(4) 2 . . . ?
C5 C6 C7 C5 -0.3(4) . . . 2_565 ?
C5 C6 C7 C8 179.5(3) . . . . ?
C7 C5 C6 C7 0.3(5) 2_565 . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.3866 0.8148 -3.3940 0.9103 -0.4138 0.0095
-3.3405 -1.0351 3.4490 -0.9089 0.4133 -0.0559
1.0552 -4.7215 1.1173 0.0485 -0.0185 -0.9987
1.5740 3.0489 1.2880 -0.1313 -0.7762 0.6167
0.7105 2.5424 -5.0529 0.8607 0.2904 0.4181
1.2032 0.5645 -4.9496 0.9480 0.3182 -0.0085
-1.4569 3.2624 2.1875 -0.6102 -0.2023 0.7660
-1.2032 -0.5645 4.9496 -0.9480 -0.3182 0.0085
3.8609 0.7226 -1.6180 0.6633 -0.7483 0.0093
-3.3698 1.8898 2.1182 -0.7649 0.3620 0.5328
-1.4162 0.6694 -4.2443 0.5484 0.8299 0.1026
-1.3136 0.0763 -4.1016 0.5509 0.8343 -0.0220
