Fused twin-acridine scaffolds as electron donors for thermally activated delayed fluorescence emitters: controllable TADF behavior by methyl substitution
Chai, Danyang; Zou, Yang; Xiang, Yepeng; Zeng, Xuan; Chen, Zhanxiang; Gong, Shaolong; Yang, Chuluo; Chemical Communications  (2019) –; doi:10.1039/C9CC08679J

data_7125632
_publ_section_title
;
 Fused twin-acridine scaffolds as electron donors for thermally activated
 delayed fluorescence emitters: controllable TADF behavior by methyl
 substitution
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC08679J
_journal_year                    2019
_chemical_formula_moiety         'C49 H42 N2 O4 S2'
_chemical_formula_sum            'C49 H42 N2 O4 S2'
_chemical_formula_weight         786.96
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc23tmq9
_audit_creation_date             2019-07-18
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2019-10-24 deposited with the CCDC.	2019-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.61240(10)
_cell_length_b                   11.87010(10)
_cell_length_c                   24.4095(2)
_cell_measurement_reflns_used    14856
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5490
_cell_measurement_theta_min      3.2470
_cell_volume                     3942.50(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     85.00 117.00   0.50    0.09    --  109.88 -46.00 117.00   64
  2  \w     86.00 178.00   0.50    0.09    --  109.88  30.00   0.00  184
  3  \w    113.00 139.00   0.50    0.09    --  109.88  61.00 120.00   52
  4  \w     94.00 176.00   0.50    0.09    --  109.88  46.00 -92.00  164
  5  \w    135.00 173.00   0.50    0.09    --  109.88  61.00-180.00   76
  6  \w     88.00 178.00   0.50    0.09    --  109.88  45.00-120.00  180
  7  \w     89.00 131.00   0.50    0.09    --  109.88  61.00-180.00   84
  8  \w     36.00 106.00   0.50    0.09    --  109.88 -94.00  30.00  140
  9  \w     58.00  87.00   0.50    0.05    --   43.30-125.00 -30.00   58
 10  \w     39.00 115.00   0.50    0.09    --  109.88-125.00 -30.00  152
 11  \w     40.00  76.00   0.50    0.09    --  109.88 -94.00  90.00   72
 12  \w     36.00 106.00   0.50    0.09    --  109.88 -94.00 150.00  140
 13  \w     -7.00  18.00   0.50    0.05    --   43.30 -46.00 117.00   50
 14  \w    -65.00  32.00   0.50    0.05    --  -43.30  46.00 -92.00  194
 15  \w    -65.00 -17.00   0.50    0.09    --  -90.25 125.00   0.00   96
 16  \w   -112.00 -58.00   0.50    0.09    --  -90.25  46.00 -92.00  108
 17  \w   -118.00 -33.00   0.50    0.05    --  -43.30 -46.00 117.00  170
 18  \w   -117.00 -92.00   0.50    0.05    --  -43.30-125.00 -90.00   50
 19  \w   -116.00 -86.00   0.50    0.05    --  -43.30-125.00-120.00   60
 20  \w   -141.00-116.00   0.50    0.09    --  -90.25 -46.00 117.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0202807000
_diffrn_orient_matrix_UB_12      0.0721859000
_diffrn_orient_matrix_UB_13      0.0508991000
_diffrn_orient_matrix_UB_21      0.1113535000
_diffrn_orient_matrix_UB_22      0.0158478000
_diffrn_orient_matrix_UB_23      0.0102396000
_diffrn_orient_matrix_UB_31      -0.0027407000
_diffrn_orient_matrix_UB_32      0.1066706000
_diffrn_orient_matrix_UB_33      -0.0359438000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25030
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         3.248
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.617
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         7049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+2.0386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6462
_reflns_number_total             7049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08679j2.cif
_cod_data_source_block           cdy-1
_cod_database_code               7125632
_shelx_shelxl_version_number     2018/1
_diffrn_oxdiff_ac3_digest_frames
;
01858e3f5100dd3683cc8c10d26a80b14302144e21e
;
_diffrn_oxdiff_ac3_digest_hkl
;
017d8c15c03495da242710023cb90e427efb80
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00J(H00J), C00N(H00N), C00R(H00R), C00S(H00S),
 C00T(H00T), C00V(H00V), C00X(H00X), C00Y(H00Y), C010(H010), C011(H011),
 C012(H012), C013(H013), C015(H015), C017(H017), C018(H018), C01B(H01J),
 C01C(H01K), C01D(H01L), C01E(H01M), C01F(H01N), C01H(H01R), C01I(H01S),
 C01J(H01T), C01K(H01U), C01L(H01V)
2.b Idealised Me refined as rotating group:
 C00Z(H00A,H00B,H00C), C014(H01A,H01B,H01C), C016(H01D,H01E,H01F), C019(H01G,
 H01H,H01I), C01G(H01O,H01P,H01Q)
;
_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 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.661