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_7237533
_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         'C42 H28 F8 N2'
_chemical_formula_sum            'C42 H28 F8 N2'
_chemical_formula_weight         712.66
_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             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                 96.16(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.791(3)
_cell_length_b                   50.622(9)
_cell_length_c                   15.001(4)
_cell_measurement_reflns_used    21469
_cell_measurement_temperature    99.97(18)
_cell_measurement_theta_max      28.7350
_cell_measurement_theta_min      2.7260
_cell_volume                     6637(3)
_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(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.883
_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    -76.00 -40.00   0.60   60.00    --   12.43 178.00  60.00   60
  2  \w     15.00  41.40   0.60   60.00    --   12.43 -99.00 -90.00   44
  3  \w     -5.00  40.00   0.60   60.00    --   12.43 -99.00 150.00   75
  4  \w    -13.00  93.20   0.60   60.00    --   12.43  19.00 -30.00  177
  5  \w     -1.00  77.00   0.60   60.00    --   12.43  37.00-150.00  130
  6  \w     19.00  76.00   0.60   60.00    --   12.43  37.00  30.00   95
  7  \w   -104.00 -79.40   0.60   60.00    --  -13.52-178.00-150.00   41
  8  \w    -14.00  15.40   0.60   60.00    --  -13.52 -99.00 -30.00   49
;
_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      -0.0054439000
_diffrn_orient_matrix_UB_12      0.0139281000
_diffrn_orient_matrix_UB_13      0.0036964000
_diffrn_orient_matrix_UB_21      0.0088411000
_diffrn_orient_matrix_UB_22      0.0012898000
_diffrn_orient_matrix_UB_23      -0.0462468000
_diffrn_orient_matrix_UB_31      -0.0804848000
_diffrn_orient_matrix_UB_32      -0.0008028000
_diffrn_orient_matrix_UB_33      -0.0104725000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       66
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            70499
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.543
_diffrn_reflns_theta_min         2.695
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81798
_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    1.426
_exptl_crystal_description       plate
_exptl_crystal_F_000             2928
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 8244 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1889
_refine_ls_number_reflns         31163
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0698P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1495
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.795
_reflns_number_gt                23810
_reflns_number_total             31163
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tc04867c2.cif
_cod_data_source_block           pfbp_1b_1
_cod_database_code               7237533
_shelx_shelxl_version_number     2014/7
_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:
 C40D(H40D), C32C(H32C), C3B(H3B), C31D(H31D), C3A(H3A), C32B(H32B),
 C34C(H34C), C43B(H43B), C34D(H34D), C32A(H32A), C34A(H34A), C6B(H6B),
 C33D(H33D), C43C(H43C), C43D(H43D), C41B(H41B), C13B(H13B), C4B(H4B), C3C(H3C),
  C14B(H14B), C15A(H15A), C15D(H15D), C32D(H32D), C4C(H4C), C33B(H33B),
 C42D(H42D), C4D(H4D), C12D(H12D), C42C(H42C), C33C(H33C), C42B(H42B),
 C33A(H33A), C31C(H31C), C14D(H14D), C42A(H42A), C34B(H34B), C14A(H14A),
 C43A(H43A), C6C(H6C), C3D(H3D), C14C(H14C), C40B(H40B), C6D(H6D), C31B(H31B),
 C13D(H13D), C5B(H5B), C12A(H12A), C12C(H12C), C41C(H41C), C40C(H40C),
 C41D(H41D), C6A(H6A), C31A(H31A), C15B(H15B), C41A(H41A), C13A(H13A), C5D(H5D),
  C4A(H4A), C12B(H12B), C13C(H13C), C5C(H5C), C5A(H5A), C40A(H40A), C15C(H15C)
2.b Idealised Me refined as rotating group:
 C38B(H38G,H38H,H38I), C37D(H37J,H37K,H37L), C37A(H37D,H37E,H37F), C10B(H10G,
 H10H,H10I), C38D(H38J,H38K,H38L), C9B(H9BA,H9BB,H9BC), C10C(H10A,H10B,H10C),
 C9C(H9CA,H9CB,H9CC), C37B(H37G,H37H,H37I), C10A(H10D,H10E,H10F), C38C(H38A,
 H38B,H38C), C10D(H10J,H10K,H10L), C38A(H38D,H38E,H38F), C9A(H9AA,H9AB,H9AC),
 C37C(H37A,H37B,H37C), C9D(H9DA,H9DB,H9DC)
;
_shelx_res_checksum              3397
_olex2_date_sample_data_collection 2018-01-26
_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 1.157
_oxdiff_exptl_absorpt_empirical_full_min 0.896