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_1567499
_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         'C61.9 H61 N3 O2, 1.5(C)'
_chemical_formula_sum            'C63.4 H61 N3 O2'
_chemical_formula_weight         896.95
_chemical_name_systematic
6-(3,6-di-tert-butyl-9H-carbazol-9-yl)-2-(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)-2,6-dimethylphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2bxvmr
_audit_creation_date             2022-04-07
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-05-13 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8808(12)
_cell_length_b                   10.3821(10)
_cell_length_c                   42.031(4)
_cell_measurement_reflns_used    575
_cell_measurement_temperature    130.0(5)
_cell_measurement_theta_max      22.1701
_cell_measurement_theta_min      2.5806
_cell_volume                     5184.4(9)
_computing_cell_refinement       'APEX3 v2019.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 V2019 (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      130.0(5)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\o and \f scans'
_diffrn_radiation_monochromator  TRIUMPH
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            67266
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.59
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'pale orange'
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1914
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.219
_refine_ls_extinction_coef       0.0086(17)
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         4597
_refine_ls_number_restraints     266
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0977
_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^)+(0.1390P)^2^+3.8835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2757
_refine_ls_wR_factor_ref         0.2877
_reflns_number_gt                3797
_reflns_number_total             4597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03342a2.cif
_cod_data_source_block           LD_KB_004
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      Pbcn
_cod_original_formula_sum        'C63.40 H61 N3 O2'
_cod_database_code               1567499
_olex2_refinement_description
;
1. Shared sites
{C37, C37B}
{C41, C41B}
2. Restrained distances
 C1A-C6A = C3A-C4A = C5A-C6A = C5A-C10A
 1.4 with sigma of 0.02
 C16A-C22A
 1.5 with sigma of 0.02
 C20A-C21A
 1.5 with sigma of 0.02
 N12A-C14A
 1.45 with sigma of 0.02
 C20B-C21B
 1.5 with sigma of 0.02
 C16B-C22B
 1.5 with sigma of 0.02
 C13B-O24B
 1.2 with sigma of 0.02
 C14B-C16B = C16B-C17B = C17B-C18B = C18B-C19B = C19B-C20B = C20B-C14B
 1.5 with sigma of 0.02
 C14A-C22A \\sim C17A-C22A
 with sigma of 0.01
 C14A-C21A \\sim C19A-C21A
 with sigma of 0.01
 C3A-N15A \\sim C18A-N37A
 with sigma of 0.01
 N15A-C25 \\sim N15A-C28
 with sigma of 0.01
3. Restrained planarity
 C14B, C16B, C17B, C18B, C19B, C20B, C21B, C22B, N12B
 with sigma of 0.02
 C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, C10B, C11B, N12B, C13B, O23B,
 O24B, C14B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C1A \\sim C20A \\sim C21A: within 15A with sigma of 0.01 and sigma for terminal
atoms of 0.01 within 15A
C2A \\sim C19A: within 15A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 15A
C5A \\sim C16A: within 15A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 15A
C6A \\sim C14A: within 15A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 15A
N15A \\sim N37A: within 20A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 20A
C1A \\sim C1B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
C2A \\sim C2B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
C3A \\sim C3B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
C6A \\sim C6B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
C8A \\sim C8B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
C9A \\sim C9B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
C13A \\sim C13B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
C17A \\sim C17B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
C18A \\sim C18B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
O23A \\sim O23B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
O24A \\sim O24B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
C20A \\sim C20B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
C22A \\sim C22B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
Uanis(C2A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C38) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C40) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C9A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N12A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C37) = Uanis(C37B)
Uanis(C41) = Uanis(C41B)
5. Same fragment restrains
{C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A, N12A, C13A, O23A,
O24A, C14A, C16A, C17A, C18A, C19A, C20A, C21A, C22A} sigma for 1-2: 0.02, 1-3:
0.04
as in
{C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, C10B, C11B, N12B, C13B, O23B,
O24B, C14B, C16B, C17B, C18B, C19B, C20B, C21B, C22B}
{C37, C38, C39, C40} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C37B, C38B, C39B, C40B}
{C41, C42, C43, C44} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C41B, C42B, C43B, C44B}
6. Others
 Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(C4B)=Sof(C5B)=Sof(C6B)=
 Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(C11B)=
 Sof(N12B)=Sof(C13B)=Sof(O23B)=Sof(O24B)=Sof(C14B)=Sof(C16B)=Sof(C17B)=
 Sof(H17B)=Sof(C18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(C21B)=Sof(H21D)=
 Sof(H21E)=Sof(H21F)=Sof(C22B)=Sof(H22D)=Sof(H22E)=Sof(H22F)=0.5*(1-FVAR(2))
 Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=
 Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(C11A)=
 Sof(N12A)=Sof(C13A)=Sof(O23A)=Sof(O24A)=Sof(C14A)=Sof(C16A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(C21A)=Sof(H21A)=
 Sof(H21B)=Sof(H21C)=Sof(C22A)=Sof(H22A)=Sof(H22B)=Sof(H22C)=0.5*FVAR(2)
 Sof(C37B)=Sof(C38B)=Sof(H38D)=Sof(H38E)=Sof(H38F)=Sof(C39B)=Sof(H39D)=
 Sof(H39E)=Sof(H39F)=Sof(C40B)=Sof(H40D)=Sof(H40E)=Sof(H40F)=1-FVAR(2)
 Sof(C37)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C39)=Sof(H39A)=Sof(H39B)=
 Sof(H39C)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H40C)=FVAR(2)
 Sof(C41B)=Sof(C42B)=Sof(H42D)=Sof(H42E)=Sof(H42F)=Sof(C43B)=Sof(H43D)=
 Sof(H43E)=Sof(H43F)=Sof(C44B)=Sof(H44D)=Sof(H44E)=Sof(H44F)=1-FVAR(3)
 Sof(C41)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=Sof(C43)=Sof(H43A)=Sof(H43B)=
 Sof(H43C)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(3)
 Fixed Sof: N37A(0.5) N15A(0.5) C1X(0.25) C2X(0.2) C3X(0.2) C4X(0.1) C5X(0.2)
 C6X(0.2) C7X(0.2) C8X(0.2) C9X(0.15)
7.a Me refined with riding coordinates:
 C22A(H22A,H22B,H22C), C21B(H21D,H21E,H21F), C22B(H22D,H22E,H22F), C38B(H38D,
 H38E,H38F), C39B(H39D,H39E,H39F), C40B(H40D,H40E,H40F), C42B(H42D,H42E,H42F),
 C43B(H43D,H43E,H43F), C44B(H44D,H44E,H44F)
7.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C7A(H7A), C8A(H8A), C9A(H9A), C17A(H17A), C19A(H19A),
 C1B(H1B), C2B(H2B), C7B(H7B), C8B(H8B), C9B(H9B), C17B(H17B), C19B(H19B),
 C29(H29), C31(H31), C32(H32), C33(H33), C34(H34), C36(H36)
7.c Fitted hexagon refined as free rotating group:
 C14A(C16A,C17A,C18A,C19A,C20A)
7.d Idealised Me refined with riding coordinates:
 C21A(H21A,H21B,H21C)
7.e Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C42(H42A,H42B,
 H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              56347
_olex2_submission_special_instructions 'No special instructions were received'