Controlling the Thermally Activated Delayed Fluorescence of Axially Chiral Organic Emitters and Their Racemate for Information Encryption
Xu, Bingjia; Song, Zicun; Zhang, Minmin; Zhang, Qingqing; Jiang, Long; Xu, Chao; Zhong, Lijun; Su, Changlin; Ban, Qiqi; Liu, Cong; Sun, Fengqiang; Zhang, Yi; Chi, Zhenguo; Zhao, Zujin; Shi, Guang; Chemical Science  (2021) –; doi:10.1039/D1SC04738H

data_1565323
_publ_section_title
;
 Controlling the Thermally Activated Delayed Fluorescence of Axially
 Chiral Organic Emitters and Their Racemate for Information Encryption
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04738H
_journal_year                    2021
_chemical_formula_moiety         'C55 H34 N4 O2, C4 H8 O2'
_chemical_formula_sum            'C59 H42 N4 O4'
_chemical_formula_weight         870.96
_chemical_name_systematic        (S)-CzACN
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-05-29 deposited with the CCDC.	2021-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8047(5)
_cell_length_b                   16.2516(8)
_cell_length_c                   26.0237(10)
_cell_measurement_reflns_used    3045
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.4470
_cell_measurement_theta_min      5.3020
_cell_volume                     4569.6(4)
_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)'
_computing_structure_solution    'ShelXT (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 0.993
_diffrn_measured_fraction_theta_max 0.962
_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      1.00  77.00   1.00   30.00    --   40.84 -99.00  90.00   76
  2  \w    -34.00  67.00   1.00   30.00    --   40.84 -37.00 -60.00  101
  3  \w     30.00  67.00   1.00   33.00    --  110.50 -94.00-150.00   37
  4  \w     61.00 135.00   1.00   33.00    --  110.50 -45.00   0.00   74
  5  \w     36.00 135.00   1.00   33.00    --  110.50 -45.00-120.00   99
  6  \w     89.00 178.00   1.00   33.00    --  110.50  77.00  30.00   89
  7  \w    106.00 170.00   1.00   33.00    --  110.50  45.00 -60.00   64
;
_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      -0.1141540000
_diffrn_orient_matrix_UB_12      -0.0248199000
_diffrn_orient_matrix_UB_13      0.0318866000
_diffrn_orient_matrix_UB_21      -0.0841504000
_diffrn_orient_matrix_UB_22      0.0475424000
_diffrn_orient_matrix_UB_23      -0.0373970000
_diffrn_orient_matrix_UB_31      -0.0149670000
_diffrn_orient_matrix_UB_32      -0.0781462000
_diffrn_orient_matrix_UB_33      -0.0330019000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_av_unetI/netI     0.1578
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14120
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.618
_diffrn_reflns_theta_min         4.431
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.04163
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       needle
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1131 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     608
_refine_ls_number_reflns         8965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0688
_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^)+(0.0572P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1894
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                5012
_reflns_number_total             8965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04738h2.cif
_cod_data_source_block           (S)-CzACN
_cod_database_code               1565323
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     (S)-CZACN
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.922
_reflns_odcompleteness_completeness 99.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.79
_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
2.a Secondary CH2 refined with riding coordinates:
 C01U(H01Z,HA)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00G(H00G), C00P(H00P), C00S(H00S), C00T(H00T), C00V(H00V),
 C00X(H00X), C014(H014), C015(H015), C018(H018), C019(H019), C01A(H01A),
 C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G),
 C01H(H01H), C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L), C01N(H01N),
 C01P(H01Q), C01Q(H01R), C01S(H01V), C01T(H01W)
2.c Idealised Me refined as rotating group:
 C01M(H01X,H01Y,H), C01O(H01M,H01O,H01P), C01R(H01S,H01T,H01U), C01V(H01,HB,HC)
;
_olex2_date_sample_data_collection 2017-12-27
_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 13.516
_oxdiff_exptl_absorpt_empirical_full_min 0.318