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_7245414
_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, C9 H6'
_chemical_formula_sum            'C12 H6 F2 O'
_chemical_formula_weight         204.17
_chemical_name_systematic        chrysene-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
_audit_creation_date             2021-04-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-17 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.61510(10)
_cell_length_b                   6.93080(10)
_cell_length_c                   18.4853(2)
_cell_measurement_reflns_used    11327
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.0520
_cell_measurement_theta_min      4.7640
_cell_volume                     845.95(2)
_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      149.99(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     30.00 119.00   0.50    0.05    --   46.43  57.00 150.00  178
  2  \w     23.00 119.00   0.50    0.05    --   46.43  77.00  30.00  192
  3  \w     30.00 119.00   0.50    0.05    --   46.43  57.00  30.00  178
  4  \w     23.00 119.00   0.50    0.05    --   46.43  77.00 -60.00  192
  5  \w     23.00 119.00   0.50    0.05    --   46.43  77.00-150.00  192
  6  \w    -39.00  28.00   0.50    0.05    --  -46.43  37.00 -30.00  134
  7  \w    -68.00 -26.00   0.50    0.05    --  -99.00  61.00-150.00   84
  8  \w    -39.00  28.00   0.50    0.05    --  -46.43  37.00  90.00  134
  9  \w     94.00 178.00   0.50    0.05    --  108.75  45.00-180.00  168
 10  \w     91.00 178.00   0.50    0.05    --  108.75  61.00-150.00  174
 11  \w     94.00 178.00   0.50    0.05    --  108.75  45.00 -60.00  168
 12  \w     85.00 178.00   0.50    0.05    --  108.75  77.00   0.00  186
 13  \w     91.00 178.00   0.50    0.05    --  108.75  61.00 120.00  174
 14  \w     36.00 109.00   0.50    0.05    --  108.75 -77.00-120.00  146
 15  \w     36.00  75.00   0.50    0.05    --  108.75 -61.00-180.00   78
 16  \w     36.00  75.00   0.50    0.05    --  108.75 -61.00 -60.00   78
 17  \w    -29.00  30.00   0.50    0.05    --   46.43 -19.00 -90.00  118
 18  \w    -25.00  63.00   0.50    0.05    --   46.43 -57.00-180.00  176
 19  \w     19.00  95.00   0.50    0.05    --   46.43-125.00-150.00  152
 20  \w     36.00 112.00   0.50    0.05    --  108.75-125.00  30.00  152
 21  \w     36.00 106.00   0.50    0.05    --  108.75 -94.00  30.00  140
 22  \w     36.00 112.00   0.50    0.05    --  108.75-125.00 120.00  152
 23  \w     36.00 112.00   0.50    0.05    --  108.75-125.00 150.00  152
 24  \w     36.00 106.00   0.50    0.05    --  108.75 -94.00 120.00  140
 25  \w   -112.00 -26.00   0.50    0.05    --  -99.00 125.00-150.00  172
 26  \w   -112.00 -26.00   0.50    0.05    --  -99.00 125.00-120.00  172
 27  \w   -112.00 -26.00   0.50    0.05    --  -99.00 125.00 150.00  172
 28  \w   -122.00 -31.00   0.50    0.05    --  -46.43 -19.00 -60.00  182
 29  \w   -119.00 -23.00   0.50    0.05    --  -46.43 -77.00-180.00  192
 30  \w   -119.00 -23.00   0.50    0.05    --  -46.43 -77.00  90.00  192
 31  \w   -172.00 -83.00   0.50    0.05    --  -99.00 -53.00 143.35  178
 32  \w   -172.00 -79.00   0.50    0.05    --  -99.00 -68.00 101.50  186
 33  \w   -172.00 -80.00   0.50    0.05    --  -99.00 -66.00  56.73  184
 34  \w   -172.00 -83.00   0.50    0.05    --  -99.00 -56.00 132.15  178
 35  \w   -172.00 -81.00   0.50    0.05    --  -99.00 -61.00  30.00  182
 36  \w   -172.00 -78.00   0.50    0.05    --  -99.00 -71.00 -41.33  188
 37  \w   -172.00-110.00   0.50    0.05    --  -99.00 -61.00 -90.00  124
 38  \w   -119.00 -74.00   0.50    0.05    --  -46.43-125.00 -90.00   90
;
_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      -0.0854914000
_diffrn_orient_matrix_UB_12      -0.2068061000
_diffrn_orient_matrix_UB_13      -0.0024742000
_diffrn_orient_matrix_UB_21      -0.2151570000
_diffrn_orient_matrix_UB_22      0.0805155000
_diffrn_orient_matrix_UB_23      0.0064627000
_diffrn_orient_matrix_UB_31      -0.0284948000
_diffrn_orient_matrix_UB_32      0.0121407000
_diffrn_orient_matrix_UB_33      -0.0832338000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14793
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.793
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81743
_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    1.603
_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         0.223
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0501P)^2^+0.2333P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1388
_reflns_number_total             1492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00925k2.cif
_cod_data_source_block           59_auto
_cod_database_code               7245414
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F)
;
_shelx_res_checksum              32931
_shelx_hkl_checksum              54979
_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 1.371
_oxdiff_exptl_absorpt_empirical_full_min 0.776