The competitive role of C–H⋯X (X = F, O) and π–π interactions in contributing to the degree of charge transfer in organic cocrystals: a case study of heteroatom-free donors with p-fluoranil (FA)
Gao, Jiaoyang; Guo, Jinjia; Chen, Yi; Deng, Shunlan; Lu, Qidong; Ren, Yuxin; Wang, Xiaoming; Fan, Haibo; Teng, Feng; He, Xuexia; Jiang, Hui; Hu, Peng; CrystEngComm  (2022) –; doi:10.1039/D2CE00925K

data_7245416
_publ_section_title
;
 The competitive role of C--H&#x22EF;X (X = F, O) and \p--\p interactions
 in contributing to the degree of charge transfer in organic cocrystals: a
 case study of heteroatom-free donors with p-fluoranil (FA)
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00925K
_journal_year                    2022
_chemical_formula_moiety         'C6 F4 O2, C18 H12'
_chemical_formula_sum            'C24 H12 F4 O2'
_chemical_formula_weight         408.34
_chemical_name_systematic        triphenylene-TFBQ
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-08-23
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_audit_update_record
;
2022-01-17 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.986(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9263(2)
_cell_length_b                   14.1750(4)
_cell_length_c                   17.3722(7)
_cell_measurement_reflns_used    19857
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      77.4370
_cell_measurement_theta_min      4.0000
_cell_volume                     1692.95(10)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     23.00 102.00   0.50    0.05    --   46.82  77.00 120.00  158
  2  \w     25.00  81.00   0.50    0.05    --   46.82  77.00-120.00  112
  3  \w     35.00  70.00   0.50    0.05    --   46.82  57.00-150.00   70
  4  \w     24.00  67.00   0.50    0.05    --   46.82  77.00-180.00   86
  5  \w     85.00 113.00   0.50    0.05    --   46.82  57.00-150.00   56
  6  \w     53.00  78.00   0.50    0.05    --   46.82  21.00  55.00   50
  7  \w     32.00  63.00   0.50    0.05    --   46.82  57.00 120.00   62
  8  \w     32.00 121.00   0.50    0.05    --   46.82  37.00  90.00  178
  9  \w    107.00 133.00   0.50    0.13    --  108.75 102.00  52.12   52
 10  \w     86.00 135.00   0.50    0.13    --  108.75  81.00  81.19   98
 11  \w     85.00 127.00   0.50    0.13    --  108.75  77.00 120.00   84
 12  \w     91.00 117.00   0.50    0.13    --  108.75  77.00 150.00   52
 13  \w    129.00 178.00   0.50    0.13    --  108.75  77.00 150.00   98
 14  \w    153.00 178.00   0.50    0.13    --  108.75  81.00  81.19   50
 15  \w     93.00 120.00   0.50    0.13    --  108.75  61.00-120.00   54
 16  \w     88.00 137.00   0.50    0.13    --  108.75  77.00-180.00   98
 17  \w     97.00 141.00   0.50    0.13    --  108.75  61.00-180.00   88
 18  \w     92.00 141.00   0.50    0.13    --  108.75  77.00-150.00   98
 19  \w    137.00 178.00   0.50    0.13    --  108.75  61.00   0.00   82
 20  \w    147.00 173.00   0.50    0.13    --  108.75  61.00  60.00   52
 21  \w     91.00 120.00   0.50    0.13    --  108.75  61.00 150.00   58
 22  \w     93.00 119.00   0.50    0.13    --  108.75  61.00 120.00   52
 23  \w     96.00 122.00   0.50    0.13    --  108.75  61.00  90.00   52
 24  \w     91.00 127.00   0.50    0.13    --  108.75  61.00-150.00   72
 25  \w    133.00 177.00   0.50    0.13    --  108.75  61.00-150.00   88
 26  \w    151.00 178.00   0.50    0.13    --  108.75  61.00-180.00   54
 27  \w    152.00 177.00   0.50    0.13    --  108.75  61.00-120.00   50
 28  \w    144.00 175.00   0.50    0.13    --  108.75  45.00 -90.00   62
 29  \w    127.00 153.00   0.50    0.13    --  108.75  45.00 -60.00   52
 30  \w     96.00 123.00   0.50    0.13    --  108.75  45.00 -90.00   54
 31  \w    103.00 132.00   0.50    0.13    --  108.75  45.00-180.00   58
 32  \w    127.00 170.00   0.50    0.13    --  108.75  45.00-120.00   86
 33  \w    148.00 174.00   0.50    0.13    --  108.75  30.00 -30.00   52
 34  \w    104.00 136.00   0.50    0.13    --  108.75  30.00 -30.00   64
 35  \w     94.00 123.00   0.50    0.13    --  108.75  30.00   0.00   58
 36  \w    138.00 173.00   0.50    0.13    --  108.75  30.00   0.00   70
 37  \w    144.00 178.00   0.50    0.13    --  108.75  35.00  80.12   68
 38  \w    110.00 176.00   0.50    0.13    --  108.75  15.00 150.00  132
 39  \w     99.00 146.00   0.50    0.13    --  108.75  30.00 150.00   94
 40  \w     94.00 129.00   0.50    0.13    --  108.75  35.00  80.12   70
 41  \w    117.00 171.00   0.50    0.13    --  108.75  21.00  55.00  108
 42  \w     96.00 178.00   0.50    0.13    --  108.75  15.00-180.00  164
 43  \w     36.00 106.00   0.50    0.13    --  108.75 -77.00  60.00  140
 44  \w     41.00  67.00   0.50    0.13    --  108.75 -61.00 120.00   52
 45  \w     46.00  91.00   0.50    0.13    --  108.75 -77.00   0.00   90
 46  \w     59.00  85.00   0.50    0.13    --  108.75 -77.00 -60.00   52
 47  \w     74.00 100.00   0.50    0.13    --  108.75 -77.00-180.00   52
 48  \w     37.00  75.00   0.50    0.13    --  108.75 -61.00 -60.00   76
 49  \w    -23.00   3.00   0.50    0.05    --   46.82 -21.00-110.00   52
 50  \w    -24.00  28.00   0.50    0.05    --   46.82 -19.00 120.00  104
 51  \w     36.00  70.00   0.50    0.13    --  108.75 -61.00 150.00   68
 52  \w     37.00  63.00   0.50    0.13    --  108.75 -61.00  90.00   52
 53  \w     45.00  73.00   0.50    0.13    --  108.75 -61.00  60.00   56
 54  \w     40.00 115.00   0.50    0.13    --  108.75 -86.00  49.72  150
 55  \w     20.00  94.00   0.50    0.05    --   46.82-125.00  60.00  148
 56  \w     82.00 110.00   0.50    0.13    --  108.75-125.00 -30.00   56
 57  \w     57.00  83.00   0.50    0.13    --  108.75-125.00 -90.00   52
 58  \w     41.00  74.00   0.50    0.13    --  108.75-125.00 -30.00   66
 59  \w     36.00  91.00   0.50    0.13    --  108.75 -94.00 -90.00  110
 60  \w     37.00  97.00   0.50    0.13    --  108.75-125.00   0.00  120
 61  \w     65.00 105.00   0.50    0.13    --  108.75 -94.00 120.00   80
 62  \w     59.00 105.00   0.50    0.13    --  108.75 -94.00 150.00   92
 63  \w     60.00 104.00   0.50    0.13    --  108.75 -94.00  30.00   88
 64  \w     72.00 105.00   0.50    0.13    --  108.75 -93.00   6.64   66
 65  \w     52.00  78.00   0.50    0.13    --  108.75 -94.00-120.00   52
 66  \w     52.00  78.00   0.50    0.13    --  108.75 -94.00-180.00   52
 67  \w   -102.00 -67.00   0.50    0.05    --  -46.82 -21.00-110.00   70
 68  \w    -68.00 -43.00   0.50    0.13    --  -99.00  61.00-150.00   50
 69  \w   -102.00 -76.00   0.50    0.13    --  -99.00 -77.00-180.00   52
 70  \w   -101.00 -76.00   0.50    0.13    --  -99.00 -77.00-150.00   50
 71  \w   -100.00 -75.00   0.50    0.13    --  -99.00 -76.00-145.55   50
 72  \w   -100.00 -75.00   0.50    0.13    --  -99.00 -76.00-165.05   50
 73  \w   -108.00 -76.00   0.50    0.13    --  -99.00 -76.00  98.39   64
 74  \w   -103.00 -77.00   0.50    0.13    --  -99.00 -74.00 162.31   52
 75  \w   -101.00 -75.00   0.50    0.13    --  -99.00 -77.00 150.00   52
 76  \w   -103.00 -77.00   0.50    0.13    --  -99.00 -73.00 153.02   52
 77  \w   -103.00 -77.00   0.50    0.13    --  -99.00 -74.00 140.34   52
 78  \w   -102.00 -77.00   0.50    0.13    --  -99.00 -73.00 157.69   50
 79  \w   -103.00 -77.00   0.50    0.13    --  -99.00 -77.00 120.00   52
 80  \w   -104.00 -78.00   0.50    0.13    --  -99.00 -72.00 121.03   52
 81  \w   -110.00 -78.00   0.50    0.13    --  -99.00 -70.00  98.61   64
 82  \w   -104.00 -78.00   0.50    0.13    --  -99.00 -69.00 126.15   52
 83  \w   -103.00 -78.00   0.50    0.13    --  -99.00 -70.00-133.89   50
 84  \w   -107.00 -81.00   0.50    0.13    --  -99.00 -68.00-166.82   52
 85  \w   -102.00 -77.00   0.50    0.13    --  -99.00 -72.00-169.25   50
 86  \w   -108.00 -82.00   0.50    0.13    --  -99.00 -66.00-147.69   52
 87  \w    -16.00  20.00   0.50    0.05    --  -46.82  21.00  55.00   72
 88  \w   -109.00 -80.00   0.50    0.13    --  -99.00 -67.00 102.50   58
 89  \w   -120.00 -79.00   0.50    0.13    --  -99.00 -67.00 140.50   82
 90  \w   -107.00 -81.00   0.50    0.13    --  -99.00 -63.00 171.03   52
 91  \w   -107.00 -81.00   0.50    0.13    --  -99.00 -61.00 150.00   52
 92  \w   -107.00 -81.00   0.50    0.13    --  -99.00 -61.00 120.00   52
 93  \w   -167.00-124.00   0.50    0.13    --  -99.00 -67.00 140.50   86
 94  \w   -153.00-128.00   0.50    0.13    --  -99.00 -21.00-110.00   50
 95  \w   -107.00 -81.00   0.50    0.13    --  -99.00 -61.00-150.00   52
 96  \w   -109.00 -84.00   0.50    0.13    --  -99.00 -45.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1979131000
_diffrn_orient_matrix_UB_12      -0.0272497000
_diffrn_orient_matrix_UB_13      0.0253752000
_diffrn_orient_matrix_UB_21      0.0838394000
_diffrn_orient_matrix_UB_22      0.0143183000
_diffrn_orient_matrix_UB_23      0.0855074000
_diffrn_orient_matrix_UB_31      -0.0632330000
_diffrn_orient_matrix_UB_32      0.1042781000
_diffrn_orient_matrix_UB_33      -0.0052262000
_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  0.0334
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36439
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         4.037
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method 'Slow cooling in acetonitril'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0888
_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^)+(0.0658P)^2^+5.1673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2312
_refine_ls_wR_factor_ref         0.2341
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2793
_reflns_number_total             3087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00925k2.cif
_cod_data_source_block           exp_959_auto
_cod_database_code               7245416
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C F O H'
_shelx_estimated_absorpt_t_max   0.806
_shelx_estimated_absorpt_t_min   0.662
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 F13, C76
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 C17, C73
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 C17, C91
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 C47, C76
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 C47, C90
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 O9, C73
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C23(H23), C28(H28), C33(H33), C49(H49), C52(H52), C56(H56),
 C65(H65), C71(H71), C77(H77), C81(H81), C95(H95)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.844