A Sterically Hindered Asymmetric D-A-D' Thermally Activated Delayed Fluorescence Emitter for Highly-Efficient Non-doped Organic Light-Emitting Diodes
Yang, Zhan; Mao, Zhu; Xu, Chao; Chen, Xiaojie; Zhao, Juan; Yang, Zhiyong; Zhang, Yi; Wu, William; Jiao, Shibo; Liu, Yang; Aldred, Matthew Phillip; Chi, Zhenguo; Chemical Science  (2019) –; doi:10.1039/C9SC01686D

data_1551958
_publ_section_title
;
 A Sterically Hindered Asymmetric D-A-D' Thermally Activated Delayed
 Fluorescence Emitter for Highly-Efficient Non-doped Organic
 Light-Emitting Diodes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01686D
_journal_year                    2019
_chemical_formula_moiety         'C36 H24 N2 O2 S2'
_chemical_formula_sum            'C36 H24 N2 O2 S2'
_chemical_formula_weight         580.69
_chemical_melting_point          547
_chemical_name_common            2CzSPz
_chemical_name_systematic        2CzDPS
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-01-18 deposited with the CCDC.    2019-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0582(2)
_cell_length_b                   13.8661(2)
_cell_length_c                   24.9576(5)
_cell_measurement_reflns_used    3767
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.3310
_cell_measurement_theta_min      4.7690
_cell_volume                     2788.66(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.963
_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     16.00  70.00   1.00    6.00    --   43.56 -99.00  60.00   54
  2  \w     51.00  86.00   1.00   24.00    --  107.38 -94.00 120.00   35
  3  \w     88.00 145.00   1.00   24.00    --  107.38  45.00 -90.00   57
  4  \w     89.00 159.00   1.00   24.00    --  107.38  15.00-180.00   70
  5  \w     34.00 102.00   1.00   24.00    --  107.38 -94.00-120.00   68
  6  \w   -104.00 -28.00   1.00    6.00    --  -38.50 -37.00-150.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0279654000
_diffrn_orient_matrix_UB_12      0.0219374000
_diffrn_orient_matrix_UB_13      -0.0598428000
_diffrn_orient_matrix_UB_21      0.0273489000
_diffrn_orient_matrix_UB_22      -0.1072811000
_diffrn_orient_matrix_UB_23      -0.0134959000
_diffrn_orient_matrix_UB_31      -0.1870614000
_diffrn_orient_matrix_UB_32      -0.0189540000
_diffrn_orient_matrix_UB_33      0.0069261000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6341
_diffrn_reflns_point_group_measured_fraction_full 0.869
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.514
_diffrn_reflns_theta_min         3.542
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.029
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       needle
_exptl_crystal_F_000             1208
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and ethanol'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1436 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0620P)^2^+0.3778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.504
_reflns_Friedel_fraction_full    0.708
_reflns_Friedel_fraction_max     0.640
_reflns_number_gt                4437
_reflns_number_total             4680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01686d2.cif
_cod_data_source_block           18041301
_cod_database_code               1551958
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N S'
_chemical_oxdiff_usercomment     2,4CzSPz
_reflns_odcompleteness_completeness 98.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C37(H37), C19(H19), C38(H38), C35(H35), C36(H36), C42(H42), C17(H17),
 C16(H16), C20(H20), C10(H10), C31(H31), C11(H11), C30(H30), C6(H6), C12(H12),
 C41(H41), C39(H39), C28(H28), C13(H13), C3(H3), C5(H5), C29(H29), C4(H4),
 C40(H40)
;
_olex2_date_sample_data_collection 2018-04-13
_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 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.663