Polymorphism of derivatives of tert-butyl substituted acridan and perfluorobiphenyl as sky-blue OLED emitters exhibiting aggregation induced thermally activated delayed fluorescence
Hladka, Iryna; Volyniuk, Dmytro; Bezvikonnyi, Oleksandr; Kinzhybalo, Vasyl; Bednarchuk, Tamara J.; Danyliv, Yan; Lytvyn, Roman; Lazauskas, Algirdas; Grazulevicius, Juozas V.; Journal of Materials Chemistry C 6 (2018) 13179–; doi:10.1039/C8TC04867C

data_7237530
_publ_section_title
;
 Polymorphism of derivatives of tert-butyl substituted acridan and
 perfluorobiphenyl as sky-blue OLED emitters exhibiting aggregation
 induced thermally activated delayed fluorescence
;
_journal_issue                   48
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              13179
_journal_paper_doi               10.1039/C8TC04867C
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C27 H14 F9 N'
_chemical_formula_sum            'C27 H14 F9 N'
_chemical_formula_weight         523.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-04 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.65(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.834(3)
_cell_length_b                   23.095(6)
_cell_length_c                   11.074(4)
_cell_measurement_reflns_used    15026
_cell_measurement_temperature    99.97(19)
_cell_measurement_theta_max      29.2850
_cell_measurement_theta_min      3.0120
_cell_volume                     2127.8(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      99.97(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.930
_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    -78.00 103.00   1.00   49.00    --   12.43   0.00 150.00  181
  2  \w    -77.00 -32.00   1.00   49.00    --   12.43 178.00-180.00   45
  3  \w    -16.00  90.00   1.00   49.00    --   12.43  37.00 -30.00  106
  4  \w    -85.00 -10.00   1.00   49.00    --  -13.52 146.00 -61.89   75
  5  \w    -19.00  88.00   1.00   49.00    --   12.43  57.00-150.00  107
  6  \w    -77.00 -32.00   1.00   49.00    --   12.43 178.00 -90.00   45
  7  \w    -76.00 -45.00   1.00   49.00    --  -13.52 132.00  83.29   31
  8  \w    -72.00   3.00   1.00   49.00    --  -13.52 125.00-171.57   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0015625000
_diffrn_orient_matrix_UB_12      0.0040134000
_diffrn_orient_matrix_UB_13      -0.0630666000
_diffrn_orient_matrix_UB_21      -0.0852241000
_diffrn_orient_matrix_UB_22      0.0004430000
_diffrn_orient_matrix_UB_23      -0.0239196000
_diffrn_orient_matrix_UB_31      0.0010370000
_diffrn_orient_matrix_UB_32      0.0304503000
_diffrn_orient_matrix_UB_33      0.0086697000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37368
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.539
_diffrn_reflns_theta_min         2.632
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0406P)^2^+0.9702P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4407
_reflns_number_total             5527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tc04867c2.cif
_cod_data_source_block           pfbp_1a
_cod_original_cell_volume        2127.8(12)
_cod_database_code               7237530
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C27H14F9N
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C14(H14), C3(H3), C5(H5), C6(H6), C4(H4), C12(H12)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              24937
_olex2_date_sample_data_collection 2018-01-30
_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 1.031
_oxdiff_exptl_absorpt_empirical_full_min 0.970