Fine-tuning of the charge-separated state energy in compact orthogonal naphthalene–phenoxazine dyads and its effect on the thermally-activated delayed fluorescence
Tang, Jieyu; Liu, Xi; Zhang, Xue; Zhao, Jianzhang; Wan, Yan; New Journal of Chemistry 47 (2023) 22418–22429; doi:10.1039/D3NJ04201D

data_7062895
_publ_section_title
;
 Fine-tuning of the charge-separated state energy in compact orthogonal
 naphthalene--phenoxazine dyads and its effect on the thermally-activated
 delayed fluorescence
;
_journal_issue                   48
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              22418
_journal_page_last               22429
_journal_paper_doi               10.1039/D3NJ04201D
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C30 H18 N2 O3'
_chemical_formula_sum            'C30 H18 N2 O3'
_chemical_formula_weight         454.46
_chemical_name_systematic        NI-PXZ-Ph
_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             2022-08-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-10 deposited with the CCDC.	2023-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7810(7)
_cell_length_b                   12.8680(6)
_cell_length_c                   13.2627(7)
_cell_measurement_reflns_used    5211
_cell_measurement_temperature    273.7
_cell_measurement_theta_max      23.081
_cell_measurement_theta_min      2.721
_cell_volume                     2181.26(19)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.7
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24469
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.724
_diffrn_reflns_theta_max         24.724
_diffrn_reflns_theta_min         2.205
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.7165
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0656 after correction.
The Ratio of minimum to maximum transmission is 0.9616.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 983 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0437P)^2^+0.2953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2789
_reflns_number_total             3716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj04201d2.cif
_cod_data_source_block           2_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7062893--7062895.cif.'
_cod_database_code               7062895
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28),
  C29(H29), C30(H30)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'