Unraveling the unusual effect of fluorination on crystal packing in an organic semiconductor.
Komissarova, Ekaterina A.; Dominskiy, Dmitry I.; Zhulanov, Vladimir E.; Abashev, George G.; Siddiqui, Afzal; Singh, Surya P.; Sosorev, Andrey Yu; Paraschuk, Dmitry Yu; Physical chemistry chemical physics : PCCP 22 (2020) 1665–1673; doi:10.1039/c9cp05455c

data_7239625
_publ_section_title
;
 Unraveling the unusual effect of fluorination on crystal packing in an
 organic semiconductor.
;
_journal_issue                   3
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              1665
_journal_page_last               1673
_journal_paper_doi               10.1039/c9cp05455c
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C26 H12 F2 N2 O4'
_chemical_formula_sum            'C26 H12 F2 N2 O4'
_chemical_formula_weight         454.38
_chemical_name_systematic
2,7-bis(4-fluorophenyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc23nvxk
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-09-28 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.82(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.538(5)
_cell_length_b                   8.3933(15)
_cell_length_c                   7.2050(18)
_cell_measurement_reflns_used    1388
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.9720
_cell_measurement_theta_min      2.5100
_cell_volume                     978.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5219
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.70
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol or Acetic acid'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1009P)^2^+0.0986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1963
_reflns_number_gt                1539
_reflns_number_total             2368
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c9cp05455c2.cif
_cod_data_source_block           psu-860(aggr-49)-4
_cod_depositor_comments          'Adding full bibliography for 7239625.cif.'
_cod_database_code               7239625