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_7245413
_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         'C3 F2 O, C8 H5'
_chemical_formula_sum            'C11 H5 F2 O'
_chemical_formula_weight         191.15
_chemical_name_systematic        pyrene-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     dual
_audit_creation_date             2021-09-14
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_audit_update_record
;
2021-12-17 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.8470(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.78250(10)
_cell_length_b                   6.93350(10)
_cell_length_c                   14.69280(10)
_cell_measurement_reflns_used    9400
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.6670
_cell_measurement_theta_min      6.0340
_cell_volume                     789.988(16)
_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      150.00(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     32.00 119.00   0.50    0.08    --   46.93  54.00  -4.00  174
  2  \w     91.00 178.00   0.50    0.30    --  108.75  61.00  60.00  174
  3  \w     94.00 178.00   0.50    0.30    --  108.75  45.00  90.00  168
  4  \w     92.00 178.00   0.50    0.30    --  108.75  54.00  -4.00  172
  5  \w     91.00 178.00   0.50    0.30    --  108.75  61.00 -90.00  174
  6  \w     23.00 119.00   0.50    0.08    --   46.93  77.00 -90.00  192
  7  \w    -23.00  29.00   0.50    0.08    --  -46.93  19.00 150.00  104
  8  \w    -68.00 -26.00   0.50    0.30    --  -99.00  61.00 120.00   84
  9  \w    -68.00 -26.00   0.50    0.30    --  -99.00  61.00  90.00   84
 10  \w    -58.00 -26.00   0.50    0.30    --  -99.00  54.00  -4.00   64
 11  \w    -68.00 -26.00   0.50    0.30    --  -99.00  61.00-180.00   84
 12  \w    -58.00  26.00   0.50    0.08    --  -46.93  54.00  -4.00  168
 13  \w   -121.00 -32.00   0.50    0.08    --  -46.93 -37.00  60.00  178
 14  \w   -119.00 -31.00   0.50    0.08    --  -46.93 -57.00 150.00  176
 15  \w   -172.00 -75.00   0.50    0.30    --  -99.00 -77.00 120.00  194
 16  \w   -172.00 -81.00   0.50    0.30    --  -99.00 -61.00 120.00  182
 17  \w   -172.00 -81.00   0.50    0.30    --  -99.00 -61.00  30.00  182
 18  \w   -172.00 -81.00   0.50    0.30    --  -99.00 -61.00  60.00  182
 19  \w   -171.00 -84.00   0.50    0.30    --  -99.00 -45.00 150.00  174
 20  \w   -171.00 -84.00   0.50    0.30    --  -99.00 -45.00 120.00  174
 21  \w   -171.00 -84.00   0.50    0.30    --  -99.00 -45.00  90.00  174
 22  \w   -171.00 -84.00   0.50    0.30    --  -99.00 -45.00  60.00  174
 23  \w   -174.00 -83.00   0.50    0.30    --  -99.00 -30.00  60.00  182
 24  \w   -174.00 -81.00   0.50    0.30    --  -99.00 -15.00  90.00  186
 25  \w   -172.00 -82.00   0.50    0.30    --  -99.00 -54.00-147.00  180
 26  \w   -119.00 -31.00   0.50    0.08    --  -46.93 -54.00-147.00  176
 27  \w    -28.00  30.00   0.50    0.08    --   46.93 -19.00-150.00  116
 28  \w     36.00  75.00   0.50    0.30    --  108.75 -61.00 -90.00   78
 29  \w     36.00 109.00   0.50    0.30    --  108.75 -77.00 -90.00  146
 30  \w     36.00  75.00   0.50    0.30    --  108.75 -61.00 -60.00   78
 31  \w     36.00  75.00   0.50    0.30    --  108.75 -61.00 -30.00   78
 32  \w     36.00  65.00   0.50    0.30    --  108.75 -54.00-147.00   58
 33  \w    -25.00  62.00   0.50    0.08    --   46.93 -54.00-147.00  174
 34  \w     36.00  75.00   0.50    0.30    --  108.75 -61.00  60.00   78
 35  \w     36.00  75.00   0.50    0.30    --  108.75 -61.00 150.00   78
 36  \w     36.00  75.00   0.50    0.30    --  108.75 -61.00  90.00   78
 37  \w     36.00 106.00   0.50    0.30    --  108.75 -94.00  30.00  140
 38  \w     36.00 112.00   0.50    0.30    --  108.75-125.00 -90.00  152
 39  \w     36.00 112.00   0.50    0.30    --  108.75-125.00-120.00  152
 40  \w     36.00 106.00   0.50    0.30    --  108.75 -94.00 -60.00  140
;
_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      0.1673233000
_diffrn_orient_matrix_UB_12      -0.0349027000
_diffrn_orient_matrix_UB_13      -0.0465913000
_diffrn_orient_matrix_UB_21      -0.0622981000
_diffrn_orient_matrix_UB_22      0.1411926000
_diffrn_orient_matrix_UB_23      -0.0767512000
_diffrn_orient_matrix_UB_31      0.0871143000
_diffrn_orient_matrix_UB_32      0.1680213000
_diffrn_orient_matrix_UB_33      0.0548411000
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14174
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.572
_diffrn_reflns_theta_max         66.572
_diffrn_reflns_theta_min         6.045
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.161
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89003
_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            'light brownish black'
_exptl_crystal_colour_lustre     light
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Benzene'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0015(5)
_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   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0452P)^2^+0.2538P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1299
_reflns_number_total             1398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00925k2.cif
_cod_data_source_block           4f_pyre_auto
_cod_database_code               7245413
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.944
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C5(H5), C4(H4)
;
_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.869