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_7237531
_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         'C35 H30 F9 N'
_chemical_formula_sum            'C35 H30 F9 N'
_chemical_formula_weight         635.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-17
_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                97.80(3)
_cell_angle_beta                 108.96(3)
_cell_angle_gamma                106.05(3)
_cell_formula_units_Z            2
_cell_length_a                   10.512(4)
_cell_length_b                   11.169(4)
_cell_length_c                   14.712(4)
_cell_measurement_reflns_used    8703
_cell_measurement_temperature    99.96(16)
_cell_measurement_theta_max      29.2990
_cell_measurement_theta_min      2.8160
_cell_volume                     1520.8(10)
_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      99.96(16)
_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 0.881
_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    -16.00  90.00   1.00   65.00    --   12.43  37.00 120.00  106
  2  \w    -77.00 -32.00   1.00   65.00    --   12.43 178.00 150.00   45
  3  \w   -104.00  77.00   1.00   65.00    --  -13.52   0.00-150.00  181
  4  \w    -91.00  15.00   1.00   65.00    --  -13.52 -37.00 120.00  106
  5  \w    -78.00  -4.00   1.00   65.00    --  -13.52 136.00  71.00   74
  6  \w    -90.00 -14.00   1.00   65.00    --  -13.52 153.00 -45.07   76
  7  \w    -93.00 -16.00   1.00   65.00    --  -13.52 156.00-172.42   77
  8  \w    -77.00 -72.00   1.00   65.00    --   12.43 178.00  90.00    5
;
_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      0.0663170000
_diffrn_orient_matrix_UB_12      0.0217149000
_diffrn_orient_matrix_UB_13      0.0410916000
_diffrn_orient_matrix_UB_21      -0.0365098000
_diffrn_orient_matrix_UB_22      0.0012647000
_diffrn_orient_matrix_UB_23      0.0328689000
_diffrn_orient_matrix_UB_31      -0.0058546000
_diffrn_orient_matrix_UB_32      -0.0646557000
_diffrn_orient_matrix_UB_33      0.0006666000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27147
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.577
_diffrn_reflns_theta_min         2.979
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95008
_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    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         7537
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0493P)^2^+0.4890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5361
_reflns_number_total             7537
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tc04867c2.cif
_cod_data_source_block           pfbp_2a_kr_b
_cod_database_code               7237531
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C35 H30 F9 N'
_reflns_odcompleteness_completeness 99.92
_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. Restrained distances
 C34-C29 = C33-C29 = C35-C29
 1.54 with sigma of 0.02
3. Others
 Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H40C)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(H41C)=
 Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=1-FVAR(1)
 Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=
 Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=FVAR(1)
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=
 Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=1-FVAR(2)
 Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=
 Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C14(H14), C4(H4), C3(H3), C6(H6)
4.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C32(H32A,H32B,H32C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C39(H39A,H39B,H39C), C38(H38A,H38B,H38C), C37(H37A,
 H37B,H37C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C),
 C34(H34A,H34B,H34C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              18547
_olex2_date_sample_data_collection 2018-01-31
_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 1.046
_oxdiff_exptl_absorpt_empirical_full_min 0.933