Helically chiral multiresonant thermally activated delayed fluorescent emitters and their use in hyperfluorescent organic light-emitting diodes.
Wang, Jingxiang; Chen, Dongyang; Moreno-Naranjo, Juan Manuel; Zinna, Francesco; Frédéric, Lucas; Cordes, David B.; McKay, Aidan P.; Fuchter, Matthew J.; Zhang, Xiaohong; Zysman-Colman, Eli; Chemical science 15 (2024) 16917–16927; doi:10.1039/d4sc03478c

data_1572638
_publ_section_title
;
 Helically chiral multiresonant thermally activated delayed fluorescent
 emitters and their use in hyperfluorescent organic light-emitting diodes.
;
_journal_issue                   41
_journal_name_full               'Chemical science'
_journal_page_first              16917
_journal_page_last               16927
_journal_paper_doi               10.1039/d4sc03478c
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C84 H78 B N3, C4 H8 O, C H4 O'
_chemical_formula_sum            'C89 H90 B N3 O2'
_chemical_formula_weight         1244.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-20
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-20 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.53694(4)
_cell_length_b                   20.05694(9)
_cell_length_c                   33.47918(14)
_cell_measurement_reflns_used    60498
_cell_measurement_temperature    173
_cell_measurement_theta_max      75.2500
_cell_measurement_theta_min      2.2490
_cell_volume                     7075.45(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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   -125.00  55.00   0.50    5.00    --  -35.00  60.00 -45.00  360
  2  \w   -108.00 -48.00   0.50    5.00    --  -35.00  30.00  90.00  120
  3  \w   -173.50 -10.00   0.50    5.00    -- -100.00  60.00 -90.00  327
  4  \w   -187.00 -40.00   0.50    5.00    -- -100.00  30.00  45.00  294
  5  \w   -165.00 -10.00   0.50    5.00    -- -100.00  60.00-180.00  310
  6  \w   -190.00-127.50   0.50    5.00    -- -100.00  60.00 135.00  125
  7  \w   -165.00 -19.00   0.50    5.00    -- -100.00  60.00   0.00  292
  8  \w   -152.50 -44.50   0.50    5.00    -- -100.00  30.00 135.00  216
  9  \w   -174.00-114.00   0.50    5.00    -- -100.00  60.00  90.00  120
 10  \w    -70.00 -10.00   0.50    5.00    -- -100.00  30.00   0.00  120
 11  \w   -190.00 -10.00   0.50    5.00    -- -100.00  30.00 -90.00  360
 12  \w   -174.00 -10.00   0.50    5.00    -- -100.00  60.00  45.00  328
 13  \w   -190.00-120.00   0.50    5.00    -- -100.00  60.00-135.00  140
;
_diffrn_measurement_device       'AFC11: Quarter \c 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1258945000
_diffrn_orient_matrix_UB_12      -0.0191700000
_diffrn_orient_matrix_UB_13      0.0203533000
_diffrn_orient_matrix_UB_21      0.0545803000
_diffrn_orient_matrix_UB_22      0.0692526000
_diffrn_orient_matrix_UB_23      -0.0100098000
_diffrn_orient_matrix_UB_31      -0.0504174000
_diffrn_orient_matrix_UB_32      0.0270903000
_diffrn_orient_matrix_UB_33      0.0400549000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            85843
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.495
_diffrn_reflns_theta_min         2.568
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       prism
_exptl_crystal_F_000             2664
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF/methanol'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 6110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     913
_refine_ls_number_reflns         14502
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0694P)^2^+1.1875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                14037
_reflns_number_total             14502
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03478c3.cif
_cod_data_source_block           DPA-tBuPh-BN
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' 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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1572637--1572638.cif.
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1572638
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.881
_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 C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O95A-C95A = O95-C95
 1.45 with sigma of 0.01
 O95A-H95D = O95-H95D
 0.98 with sigma of 0.02
 C63A-C61 = C62A-C61 = C64A-C61
 1.53 with sigma of 0.02
 C63A-C64A = C64A-C62A = C63A-C62A
 2.51 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C61 \\sim C62 \\sim C63 \\sim C64 \\sim C62A \\sim C63A \\sim C64A: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C63) \\sim Ueq, Uanis(C64) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Sof(C62A)=Sof(H62D)=Sof(H62E)=Sof(H62F)=Sof(C63A)=Sof(H63D)=Sof(H63E)=
 Sof(H63F)=Sof(C64A)=Sof(H64D)=Sof(H64E)=Sof(H64F)=1-FVAR(1)
 Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(H63C)=
 Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(H64C)=FVAR(1)
 Sof(O95A)=Sof(H95D)=Sof(C95A)=Sof(H95E)=Sof(H95F)=Sof(H95G)=1-FVAR(2)
 Sof(O95)=Sof(H95)=Sof(C95)=Sof(H95A)=Sof(H95B)=Sof(H95C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C91(H91A,H91B), C92(H92A,H92B), C93(H93A,H93B), C94(H94A,H94B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C32(H32), C33(H33), C35(H35), C36(H36), C39(H39),
  C40(H40), C42(H42), C43(H43), C46(H46), C47(H47), C49(H49), C50(H50),
 C56(H56), C57(H57), C59(H59), C60(H60), C66(H66), C67(H67), C69(H69), C70(H70),
  C76(H76), C77(H77), C79(H79), C80(H80)
5.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C44(H44A,H44B,H44C), C52(H52A,H52B,H52C), C53(H53A,H53B,
 H53C), C54(H54A,H54B,H54C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C64(H64A,
 H64B,H64C), C62A(H62D,H62E,H62F), C63A(H63D,H63E,H63F), C64A(H64D,H64E,H64F),
 C72(H72A,H72B,H72C), C73(H73A,H73B,H73C), C74(H74A,H74B,H74C), C82(H82A,H82B,
 H82C), C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C95(H95A,H95B,H95C),
 C95A(H95E,H95F,H95G)
;
_shelx_res_checksum              89267
_shelx_hkl_checksum              17594