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_7062893
_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         'C31 H19 N2 O4'
_chemical_formula_sum            'C31 H19 N2 O4'
_chemical_formula_weight         483.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-19
_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                 105.684(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6346(8)
_cell_length_b                   22.406(3)
_cell_length_c                   12.3194(14)
_cell_measurement_reflns_used    2395
_cell_measurement_temperature    294.8
_cell_measurement_theta_max      21.659
_cell_measurement_theta_min      2.501
_cell_volume                     2294.7(5)
_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      294.8
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0964
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16901
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.016
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         2.501
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1470 before and 0.0805 after correction.
The Ratio of minimum to maximum transmission is 0.8829.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0117(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4021
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.2042
_refine_ls_R_factor_gt           0.1254
_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^)+10.7092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2392
_refine_ls_wR_factor_ref         0.2784
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2140
_reflns_number_total             4021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj04201d2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7062893--7062895.cif.'
_cod_original_cell_volume        2294.7(4)
_cod_database_code               7062893
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.955
_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. Restrained distances
 N2A-C14 \\sim N2B-C19
 with sigma of 0.02
 N2A-C20 \\sim N2B-C20
 with sigma of 0.02
 N2A-C27 \\sim N2B-C27
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C20, N2B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C20, N2A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Fixed Sof: N2B(0.5) N2A(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C24(H24), C4(H4), C7(H7), C17(H17), C18(H18), C23(H23), C31(H31),
 C22(H22), C3(H3), C30(H30), C29(H29), C21(H21), C28(H28), C12(H12), C13(H13)
5.b Fitted hexagon refined as free rotating group:
 C14(C15,C16,C10,C12,C13)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              48159
_olex2_submission_special_instructions 'No special instructions were received'