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_1565324
_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         'C H2 Cl2, C55 H34 N4 O2'
_chemical_formula_sum            'C56 H36 Cl2 N4 O2'
_chemical_formula_weight         867.79
_chemical_name_systematic        (R,S)-CzACN-SCrr
_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_creation_date             2020-10-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2021-06-29 deposited with the CCDC.	2021-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.183(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.1331(13)
_cell_length_b                   8.9596(5)
_cell_length_c                   19.2248(11)
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      59.048
_cell_measurement_theta_min      4.293
_cell_volume                     4322.4(4)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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_temperature      149.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON III'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            49979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         59.629
_diffrn_reflns_theta_min         1.532
_exptl_absorpt_coefficient_mu    1.134
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1468 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.8836.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       prism
_exptl_crystal_F_000             1800
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and ethanol'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         9594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.1095
_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^)+(0.0911P)^2^+16.2063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2747
_refine_ls_wR_factor_ref         0.2956
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6537
_reflns_number_total             9594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04738h2.cif
_cod_data_source_block           RS-CzACN-SCrr
_cod_database_code               1565324
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     RS-CzACN
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.805
_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:
 C01Q(H01T,H01U)
2.b Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00S(H00S), C00T(H00T),
 C00V(H00V), C00W(H00W), C00X(H00X), C013(H013), C014(H014), C015(H015),
 C017(H017), C018(H018), C019(H019), C01A(H01A), C01C(H01C), C01D(H01D),
 C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H), C01I(H01I), C01J(H01J),
 C01K(H01K), C01N(H01N), C01O(H01O), C01P(H01P)
2.c Idealised Me refined as rotating group:
 C01R(H01B,H01L,H01M), C01S(H01Q,H01R,H01S)
;
_shelx_res_checksum              53166
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'