Thermally activated delayed fluorescence emitters showing wide-range near-infrared piezochromism and their use in deep-red OLEDs.
Sudhakar, Pagidi; Gupta, Abhishek Kumar; Cordes, David B.; Zysman-Colman, Eli; Chemical science 15 (2024) 545–554; doi:10.1039/d3sc05188a

data_1570413
_publ_section_title
;
 Thermally activated delayed fluorescence emitters showing wide-range
 near-infrared piezochromism and their use in deep-red OLEDs.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              545
_journal_page_last               554
_journal_paper_doi               10.1039/d3sc05188a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C64 H64 N4 O2'
_chemical_formula_sum            'C64 H64 N4 O2'
_chemical_formula_weight         921.19
_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     direct
_audit_creation_date             2023-09-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                76.932(4)
_cell_angle_beta                 86.233(3)
_cell_angle_gamma                86.248(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9658(2)
_cell_length_b                   17.8685(7)
_cell_length_c                   25.1599(10)
_cell_measurement_reflns_used    5175
_cell_measurement_temperature    125
_cell_measurement_theta_max      74.3830
_cell_measurement_theta_min      2.7690
_cell_volume                     2603.41(17)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'SIR2011  (Burla et al.,  2007)'
_diffrn_ambient_temperature      125
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.948
_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   12.00    --  -35.00  60.00 -45.00  360
  2  \w   -108.00 -48.00   0.50   12.00    --  -35.00  30.00  90.00  120
  3  \w   -173.50 -10.00   0.50   25.00    -- -100.00  60.00 -90.00  327
  4  \w   -187.00 -40.00   0.50   25.00    -- -100.00  30.00  45.00  294
  5  \w   -165.00 -10.00   0.50   25.00    -- -100.00  60.00-180.00  310
  6  \w   -190.00-127.50   0.50   25.00    -- -100.00  60.00 135.00  125
  7  \w   -165.00 -19.00   0.50   25.00    -- -100.00  60.00   0.00  292
  8  \w   -152.50 -44.50   0.50   25.00    -- -100.00  30.00 135.00  216
  9  \w   -174.00-114.00   0.50   25.00    -- -100.00  60.00  90.00  120
 10  \w    -70.00 -10.00   0.50   25.00    -- -100.00  30.00   0.00  120
 11  \w   -190.00 -10.00   0.50   25.00    -- -100.00  30.00 -90.00  360
 12  \w   -174.00 -10.00   0.50   25.00    -- -100.00  60.00  45.00  328
 13  \w   -190.00-120.00   0.50   25.00    -- -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      -0.0592873000
_diffrn_orient_matrix_UB_12      0.0418664000
_diffrn_orient_matrix_UB_13      -0.0582956000
_diffrn_orient_matrix_UB_21      -0.2444189000
_diffrn_orient_matrix_UB_22      -0.0242382000
_diffrn_orient_matrix_UB_23      0.0124734000
_diffrn_orient_matrix_UB_31      -0.0624472000
_diffrn_orient_matrix_UB_32      0.0742615000
_diffrn_orient_matrix_UB_33      0.0202018000
_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  0.0948
_diffrn_reflns_av_unetI/netI     0.1044
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30125
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.424
_diffrn_reflns_theta_min         1.805
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         10255
_refine_ls_number_restraints     207
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0752P)^2^+0.0171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5983
_reflns_number_total             10255
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05188a3.cif
_cod_data_source_block           tBuTPA-BQ
_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 1570412--1570413.cif.
;
_cod_original_cell_volume        2603.41(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1570413
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.948
_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
 C66A-C65 = C66-C65 = C68A-C65 = C68-C65 = C67A-C65 = C67-C65 = C41A-C38 = C39-
 C38 = C39A-C38 = C40-C38 = C40A-C38 = C41-C38
 1.53 with sigma of 0.02
 C67A-C66A = C67A-C68A = C66A-C68A
 2.51 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C38 \\sim C39 \\sim C39A \\sim C40 \\sim C40A \\sim C41 \\sim C41A \\sim C65
\\sim C66 \\sim C66A \\sim C67 \\sim C67A \\sim C68 \\sim C68A: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C38, C39, C39A, C40, C40A, C41, C41A, C65, C66, C67, C68
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C39A)=Sof(H39D)=Sof(H39E)=Sof(H39F)=Sof(C40A)=Sof(H40D)=Sof(H40E)=
 Sof(H40F)=Sof(C41A)=Sof(H41D)=Sof(H41E)=Sof(H41F)=1-FVAR(1)
 Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H40C)=
 Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(H41C)=FVAR(1)
 Sof(C66A)=Sof(H66D)=Sof(H66E)=Sof(H66F)=Sof(C67A)=Sof(H67D)=Sof(H67E)=
 Sof(H67F)=Sof(C68A)=Sof(H68D)=Sof(H68E)=Sof(H68F)=1-FVAR(2)
 Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(H67C)=
 Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(H68C)=FVAR(2)
6.a Me refined with riding coordinates:
 C66A(H66D,H66E,H66F), C67A(H67D,H67E,H67F), C68A(H68D,H68E,H68F)
6.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C19(H19), C20(H20),
 C23(H23), C24(H24), C26(H26), C27(H27), C33(H33), C34(H34), C36(H36), C37(H37),
  C43(H43), C44(H44), C46(H46), C47(H47), C50(H50), C51(H51), C53(H53),
 C54(H54), C60(H60), C61(H61), C63(H63), C64(H64)
6.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C39(H39A,H39B,
 H39C), C39A(H39D,H39E,H39F), C40(H40A,H40B,H40C), C40A(H40D,H40E,H40F),
 C41(H41A,H41B,H41C), C41A(H41D,H41E,H41F), C56(H56A,H56B,H56C), C57(H57A,H57B,
 H57C), C58(H58A,H58B,H58C), C66(H66A,H66B,H66C), C67(H67A,H67B,H67C), C68(H68A,
 H68B,H68C)
;
_shelx_res_checksum              69443