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_7245415
_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        BA-TFBQ
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-17
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2021-12-17 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9097(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.67424(4)
_cell_length_b                   7.45602(5)
_cell_length_c                   17.58647(11)
_cell_measurement_reflns_used    19978
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      77.2990
_cell_measurement_theta_min      2.5070
_cell_volume                     874.674(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    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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     85.00 178.00   0.50    0.05    --  108.75  77.00   0.00  186
  2  \w     91.00 178.00   0.50    0.05    --  108.75  61.00  60.00  174
  3  \w     94.00 176.00   0.50    0.05    --  108.75  45.00 150.00  164
  4  \w     85.00 113.00   0.50    0.05    --  108.75  77.00  30.00   56
  5  \w    106.00 131.00   0.50    0.05    --  108.75  45.00 120.00   50
  6  \w    138.00 165.00   0.50    0.05    --  108.75  45.00 120.00   54
  7  \w    133.00 159.00   0.50    0.05    --  108.75  30.00  90.00   52
  8  \w    148.00 173.00   0.50    0.05    --  108.75  30.00  60.00   50
  9  \w     93.00 178.00   0.50    0.05    --  108.75  30.00 120.00  170
 10  \w     95.00 168.00   0.50    0.05    --  108.75  61.00  30.00  146
 11  \w     93.00 178.00   0.50    0.05    --  108.75  30.00 -60.00  170
 12  \w     89.00 115.00   0.50    0.05    --  108.75  77.00-150.00   52
 13  \w     91.00 178.00   0.50    0.05    --  108.75  61.00-150.00  174
 14  \w    116.00 178.00   0.50    0.05    --  108.75  30.00-180.00  124
 15  \w    146.00 175.00   0.50    0.05    --  108.75  15.00-120.00   58
 16  \w     95.00 141.00   0.50    0.05    --  108.75  15.00-120.00   92
 17  \w     36.00 136.00   0.50    0.05    --  108.75 -84.00  70.61  200
 18  \w     36.00 112.00   0.50    0.05    --  108.75-125.00  60.00  152
 19  \w     36.00 133.00   0.50    0.05    --  108.75-157.00  66.00  194
 20  \w     36.00 112.00   0.50    0.05    --  108.75-125.00 120.00  152
 21  \w     36.00 116.00   0.50    0.05    --   46.82-157.00  66.00  160
 22  \w     64.00 108.00   0.50    0.05    --  108.75-125.00  90.00   88
 23  \w     36.00 112.00   0.50    0.05    --  108.75-125.00  30.00  152
 24  \w     62.00 101.00   0.50    0.05    --  108.75-125.00   0.00   78
 25  \w     15.00  93.00   0.50    0.05    --   46.82-119.00-138.00  156
 26  \w     36.00 112.00   0.50    0.05    --  108.75-125.00-180.00  152
 27  \w     75.00 106.00   0.50    0.05    --  108.75-100.00-153.11   62
 28  \w     36.00 106.00   0.50    0.05    --  108.75 -94.00-150.00  140
 29  \w     36.00 110.00   0.50    0.05    --  108.75-119.00-138.00  148
 30  \w     78.00 107.00   0.50    0.05    --  108.75-105.00-136.59   58
 31  \w     36.00  68.00   0.50    0.05    --  108.75-105.00-136.59   64
 32  \w     36.00 137.00   0.50    0.05    --  108.75 -87.00-142.15  202
 33  \w     58.00 100.00   0.50    0.05    --  108.75 -94.00 -60.00   84
 34  \w     36.00 106.00   0.50    0.05    --  108.75 -94.00 120.00  140
 35  \w     36.00  69.00   0.50    0.05    --  108.75 -94.00  90.00   66
 36  \w     38.00  64.00   0.50    0.05    --  108.75 -94.00  30.00   52
 37  \w     44.00  70.00   0.50    0.05    --  108.75 -58.00-103.92   52
 38  \w     49.00  75.00   0.50    0.05    --  108.75 -77.00 -90.00   52
 39  \w     36.00  75.00   0.50    0.05    --  108.75 -61.00-120.00   78
 40  \w     79.00 104.00   0.50    0.05    --  108.75 -77.00-150.00   50
 41  \w     36.00  75.00   0.50    0.05    --  108.75 -61.00 -90.00   78
 42  \w     36.00  75.00   0.50    0.05    --  108.75 -61.00-150.00   78
 43  \w     36.00  75.00   0.50    0.05    --  108.75 -61.00   0.00   78
 44  \w     36.00  75.00   0.50    0.05    --  108.75 -61.00  30.00   78
 45  \w     36.00  75.00   0.50    0.05    --  108.75 -61.00  90.00   78
 46  \w     41.00  70.00   0.50    0.05    --  108.75 -70.00 147.36   58
 47  \w    -28.00  30.00   0.50    0.05    --   46.82 -19.00-180.00  116
 48  \w     84.00 178.00   0.50    0.05    --  108.75 119.00 -53.00  188
 49  \w     58.00 120.00   0.50    0.05    --   46.82 157.00 101.00  124
 50  \w    -23.00  29.00   0.50    0.05    --  -46.82  19.00  90.00  104
 51  \w    -23.00  29.00   0.50    0.05    --  -46.82  19.00 -60.00  104
 52  \w    -23.00  29.00   0.50    0.05    --  -46.82  19.00-120.00  104
 53  \w   -108.00 -26.00   0.50    0.05    --  -99.00 111.00-122.15  164
 54  \w   -110.00 -26.00   0.50    0.05    --  -99.00 119.00 -53.00  168
 55  \w   -133.00 -30.00   0.50    0.05    --  -99.00 157.00 101.00  206
 56  \w   -125.00 -26.00   0.50    0.05    --  -99.00 143.00 -43.95  198
 57  \w   -112.00 -26.00   0.50    0.05    --  -99.00 125.00-120.00  172
 58  \w   -172.00 -78.00   0.50    0.05    --  -99.00-119.00-138.00  188
 59  \w   -120.00 -74.00   0.50    0.05    --  -46.82-125.00 -60.00   92
 60  \w   -120.00 -74.00   0.50    0.05    --  -46.82-125.00   0.00   92
 61  \w   -120.00 -74.00   0.50    0.05    --  -46.82-125.00  30.00   92
 62  \w   -120.00 -52.00   0.50    0.05    --  -46.82-157.00  66.00  136
 63  \w   -160.00 -52.00   0.50    0.05    --  -99.00-157.00  66.00  216
 64  \w   -120.00 -74.00   0.50    0.05    --  -46.82-125.00-120.00   92
;
_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      -0.0313629000
_diffrn_orient_matrix_UB_12      -0.0209055000
_diffrn_orient_matrix_UB_13      -0.0867415000
_diffrn_orient_matrix_UB_21      0.0329876000
_diffrn_orient_matrix_UB_22      -0.2037663000
_diffrn_orient_matrix_UB_23      0.0075616000
_diffrn_orient_matrix_UB_31      -0.2264225000
_diffrn_orient_matrix_UB_32      -0.0269053000
_diffrn_orient_matrix_UB_33      0.0101303000
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21103
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         2.514
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72538
_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            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_recrystallization_method 'slowing cooling by chlorobezene'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1377 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0599P)^2^+0.3532P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3042
_reflns_number_total             3064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00925k2.cif
_cod_data_source_block           171_auto
_cod_depositor_comments
;

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C12 H6 F2 O'
_cod_original_formula_weight         204.17
_cod_original_formula_moiety         '0.5(C6 F4 O2), 0.5(C18 H12)'
_cod_original_formula_units_Z            4
_cod_database_code               7245415
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C13(H13), C1(H1), C11(H11), C3(H3), C16(H16), C15(H15), C6(H6),
 C10(H10), C8(H8), C9(H9), C2(H2)
;
_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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.749