Tandem rigidification and π-extension as a key tool for the development of a narrow linewidth yellow hyperfluorescent OLED system
Bartkowski, Krzysztof; Zimmermann Crocomo, Paola; Kochman, Michał Andrzej; Kumar, Dharmandra; Kubas, Adam; Data, Przemysław; Lindner, Marcin; Chemical Science  (2022) –; doi:10.1039/D2SC03342A

data_1567500
_publ_section_title
;
 Tandem rigidification and \p-extension as a key tool for the development
 of a narrow linewidth yellow hyperfluorescent OLED system
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC03342A
_journal_year                    2022
_chemical_formula_moiety         'C44 H46 N2 O2'
_chemical_formula_sum            'C44 H46 N2 O2'
_chemical_formula_weight         634.868
_chemical_name_systematic
6-(3,6-di-tert-butyl-9H-carbazol-9-yl)-2-(2,6-diisopropylphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
_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'
_symmetry_Int_Tables_number      14
_audit_block_doi                 10.5517/ccdc.csd.cc2c2lfh
_audit_creation_date             2022-05-19
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-06 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.270(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2674(6)
_cell_length_b                   9.7620(3)
_cell_length_c                   22.2538(7)
_cell_measurement_reflns_used    7292
_cell_measurement_temperature    99.95(16)
_cell_measurement_theta_max      70.5700
_cell_measurement_theta_min      4.1740
_cell_volume                     3562.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.95(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9950
_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     40.00  67.00   1.00    9.20    --    0.00  57.00  60.00   27
  2  \w      2.00  29.00   1.00    9.20    --    0.00 -77.00 -90.00   27
  3  \w     37.00  73.00   1.00   36.81    --   36.91-125.00-180.00   36
  4  \w     16.00  82.00   1.00   36.81    --   36.91  37.00 120.00   66
  5  \w     51.00  85.00   1.00   36.81    --   36.91-125.00   0.00   34
  6  \w     17.00  99.00   1.00   36.81    --   36.91  37.00  30.00   82
  7  \w     34.00  59.00   1.00   36.81    --   36.91 -37.00 120.00   25
  8  \w    -32.00  55.00   1.00   36.81    --   36.91 -57.00-120.00   87
  9  \w     71.00  98.00   1.00   50.00    --  108.00-111.00-180.00   27
 10  \w    144.00 171.00   1.00   50.00    --  108.00 111.00-180.00   27
 11  \w     38.00  67.00   1.00   50.00    --  108.00-111.00-180.00   29
 12  \w     62.00 103.00   1.00   50.00    --  108.00 178.00 -60.00   41
 13  \w     43.00  73.00   1.00   50.00    --  108.00 -37.00  90.00   30
 14  \w     79.00 106.00   1.00   50.00    --  108.00 -37.00  90.00   27
 15  \w     91.00 128.00   1.00   50.00    --  108.00 -63.00  60.00   37
 16  \w     72.00 133.00   1.00   50.00    --  108.00 -25.00   0.00   61
 17  \w     51.00  77.00   1.00   50.00    --  108.00 -25.00 -60.00   26
 18  \w     41.00  87.00   1.00   50.00    --  108.00 -50.00  60.00   46
 19  \w     80.00 109.00   1.00   50.00    --  108.00 -25.00 150.00   29
 20  \w     40.00 107.00   1.00   50.00    --  108.00 -37.00-172.00   67
 21  \w     93.00 135.00   1.00   50.00    --  108.00 -25.00 -60.00   42
 22  \w    143.00 176.00   1.00   50.00    --  108.00  37.00-150.00   33
 23  \w     78.00 154.00   1.00   50.00    --  108.00  25.00   0.00   76
 24  \w     77.00 119.00   1.00   50.00    --  108.00 -63.00   0.00   42
 25  \w     71.00 104.00   1.00   50.00    --  108.00 -91.00-120.00   33
 26  \w    121.00 146.00   1.00   50.00    --  108.00 178.00 -60.00   25
 27  \w     90.00 128.00   1.00   50.00    --  108.00 -63.00-180.00   38
 28  \w     57.00  84.00   1.00   50.00    --  108.00 -91.00 120.00   27
 29  \w    111.00 140.00   1.00   50.00    --  108.00 178.00  60.00   29
 30  \w     93.00 162.00   1.00   50.00    --  108.00  63.00  30.00   69
 31  \w    139.00 166.00   1.00   50.00    --  108.00  50.00 -60.00   27
 32  \w    105.00 130.00   1.00   50.00    --  108.00  50.00 -60.00   25
 33  \w     88.00 113.00   1.00   50.00    --  108.00  37.00   0.00   25
 34  \w     45.00  70.00   1.00   50.00    --  108.00 -12.00 150.00   25
 35  \w    108.00 135.00   1.00   50.00    --  108.00 -12.00 150.00   27
 36  \w    105.00 130.00   1.00   50.00    --  108.00 111.00 -30.00   25
 37  \w     40.00  66.00   1.00   50.00    --  108.00 -63.00  60.00   26
 38  \w     88.00 115.00   1.00   50.00    --  108.00 -77.00-150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0830761000
_diffrn_orient_matrix_UB_12      -0.0057387000
_diffrn_orient_matrix_UB_13      -0.0524668000
_diffrn_orient_matrix_UB_21      0.0400117000
_diffrn_orient_matrix_UB_22      -0.0749217000
_diffrn_orient_matrix_UB_23      -0.0435787000
_diffrn_orient_matrix_UB_31      -0.0181890000
_diffrn_orient_matrix_UB_32      -0.1387161000
_diffrn_orient_matrix_UB_33      0.0257327000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.9991
_diffrn_reflns_Laue_measured_fraction_max 0.9950
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22025
_diffrn_reflns_point_group_measured_fraction_full 0.9991
_diffrn_reflns_point_group_measured_fraction_max 0.9950
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         70.67
_diffrn_reflns_theta_min         2.69
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.555
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1364.059
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.9962
_refine_diff_density_min         -0.4716
_refine_diff_density_rms         0.0854
_refine_ls_d_res_high            0.8170
_refine_ls_d_res_low             16.3969
_refine_ls_goodness_of_fit_ref   1.0543
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    96
_refine_ls_number_parameters     495
_refine_ls_number_reflns         6805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0543
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0764
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+6.0025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.1932
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -21
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                5423
_reflns_number_total             6805
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2sc03342a2.cif
_cod_data_source_block           ml91_01
_cod_database_code               1567500
_chemical_oxdiff_formula         'C44 H46 N2 O2'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All H(C) groups, All C(H,H,H) groups
2. Others
 Sof(H42a)=Sof(C44)=Sof(H44d)=Sof(H44e)=Sof(H44f)=Sof(C43)=Sof(H43d)=Sof(H43e)=
 Sof(H43f)=1-FVAR(1)
 Sof(H42)=Sof(C44A)=Sof(H44a)=Sof(H44b)=Sof(H44c)=Sof(C43A)=Sof(H43a)=
 Sof(H43b)=Sof(H43c)=FVAR(1)
 Sof(C20A)=Sof(C18A)=Sof(H20a)=Sof(H20b)=Sof(H20c)=Sof(H18a)=Sof(H18b)=
 Sof(H18c)=Sof(C19A)=Sof(H)=Sof(H5b)=Sof(H5c)=Sof(H19a)=Sof(H19b)=Sof(H19c)=1-
 FVAR(2)
 Sof(C20)=Sof(C18)=Sof(H20d)=Sof(H20e)=Sof(H20f)=Sof(H18d)=Sof(H18e)=Sof(H18f)=
 Sof(C19)=Sof(H19d)=Sof(H19e)=Sof(H19f)=FVAR(2)
 Fixed U22: H(11.123435)
3.a Ternary CH refined with riding coordinates:
 C39(H39), C42(H42), C42(H42a)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C29(H29), C23(H23), C3(H3), C22(H22), C35(H35), C2(H2), C27(H27),
 C28(H28), C11(H11), C8(H8), C37(H37), C10(H10), C36(H36)
3.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C41(H41a,H41b,
 H41c), C40(H40a,H40b,H40c), C44A(H44a,H44b,H44c), C43A(H43a,H43b,H43c),
 C44(H44d,H44e,H44f), C43(H43d,H43e,H43f), C20(H20d,H20e,H20f), C20A(H20a,H20b,
 H20c), C18(H18d,H18e,H18f), C18A(H18a,H18b,H18c), C19(H19d,H19e,H19f),
 C19A(H19a,H19b,H19c)
;
_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 1.622
_oxdiff_exptl_absorpt_empirical_full_min 0.520