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_7237532
_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      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                 105.57(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.870(4)
_cell_length_b                   24.126(6)
_cell_length_c                   12.550(4)
_cell_measurement_reflns_used    1964
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.8710
_cell_measurement_theta_min      2.4460
_cell_volume                     3170.5(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -66.00 116.00   1.00   20.00    --   30.10  54.00   0.00  182
  2  \w     86.00 112.00   1.00   20.00    --   30.10  54.00-150.00   26
  3  \w    -73.00 -37.00   1.00   20.00    --   30.10  54.00 120.00   36
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0532954000
_diffrn_orient_matrix_UB_12      -0.0131590000
_diffrn_orient_matrix_UB_13      0.0365781000
_diffrn_orient_matrix_UB_21      -0.0408387000
_diffrn_orient_matrix_UB_22      -0.0206845000
_diffrn_orient_matrix_UB_23      0.0115181000
_diffrn_orient_matrix_UB_31      0.0090476000
_diffrn_orient_matrix_UB_32      -0.0161597000
_diffrn_orient_matrix_UB_33      -0.0445263000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1328
_diffrn_reflns_av_unetI/netI     0.1500
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13429
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.120
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.348
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6480
_refine_ls_number_restraints     106
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.2018
_refine_ls_R_factor_gt           0.0961
_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^)+(0.1536P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2399
_refine_ls_wR_factor_ref         0.3362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2086
_reflns_number_total             6480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tc04867c2.cif
_cod_data_source_block           ih_56a_rep_2abs
_cod_database_code               7237532
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C35H30F9N
_reflns_odcompleteness_completeness 99.94
_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
 C33-C38 \\sim C36-C33 \\sim C39-C33 \\sim C34-C33 \\sim C37-C33 \\sim C35-C33
 with sigma of 0.02
3. Rigid bond restraints
 C13, C33, C39, C34, C37, C35, C38, C36
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C35 \\sim C38 \\sim C36 \\sim C39 \\sim C34 \\sim C37 \\sim C33: within 1.7A
with sigma of 0.04 and sigma for terminal atoms of 0.08
5. Others
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=
 Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=1-FVAR(1)
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C4(H4), C3(H3), C15(H15), C14(H14)
6.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C31(H31A,H31B,
 H31C), C30(H30A,H30B,H30C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              44609
_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 3.534
_oxdiff_exptl_absorpt_empirical_full_min 0.420