An umpolung strategy for rapid access to thermally activated delayed fluorescence (TADF) materials based on phenazine
Zhang, Huaxing; Guo, Qiang; Cheng, Hu; Ran, Chunhao; Wu, Di; Lan, Jingbo; Chemical Communications  (2022) –; doi:10.1039/D1CC06705B

data_7129555
_publ_section_title
;
 An umpolung strategy for rapid access to thermally activated delayed
 fluorescence (TADF) materials based on phenazine
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06705B
_journal_year                    2022
_chemical_formula_moiety         'C18 H10 N2 O'
_chemical_formula_sum            'C18 H10 N2 O'
_chemical_formula_weight         270.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-21 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.483(3)
_cell_length_b                   3.8577(3)
_cell_length_c                   25.757(3)
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      23.337
_cell_measurement_theta_min      2.248
_cell_volume                     2532.1(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      302.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1241
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            34196
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.248
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0869 before and 0.0724 after correction.
The Ratio of minimum to maximum transmission is 0.8873.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5773
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1727
_refine_ls_R_factor_gt           0.0810
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1244P)^2^+0.8615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2076
_refine_ls_wR_factor_ref         0.2710
_reflns_Friedel_coverage         0.957
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2804
_reflns_number_total             5773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06705b2.cif
_cod_data_source_block           mo_zhx_4223_0ma_a
_cod_original_cell_volume        2532.1(4)
_cod_database_code               7129555
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C37-C38
 1.4 with sigma of 0.01
 C33-C19
 1.4 with sigma of 0.01
 C20-C19
 1.4 with sigma of 0.01
 C28-C29
 1.4 with sigma of 0.01
 C28-C27
 1.4 with sigma of 0.01
 C27-C26
 1.4 with sigma of 0.01
 C19-C20
 1.4 with sigma of 0.01
 C19-C33
 1.4 with sigma of 0.01
 C33-C32
 1.4 with sigma of 0.01
 C21-C22
 1.38 with sigma of 0.01
3. Rigid bond restraints
 N23, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N23 \\sim C22: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C27(H27), C28(H28), C29(H29), C32(H32),
  C33(H33), C34(H34), C37(H37), C38(H38)
;
_shelx_res_checksum              54146
_olex2_submission_special_instructions 'No special instructions were received'