Efficient orange and red thermally activated delayed fluorescence materials based on 1,8-naphthalimide derivatives
Chen, Meiling; Chen, Yuzhuo; Li, Yan; Lin, Yuhong; Wu, Yunan; RSC Advances 14 (2024) 6494–6500; doi:10.1039/D3RA08969J

data_7248210
_publ_section_title
;
 Efficient orange and red thermally activated delayed fluorescence
 materials based on 1,8-naphthalimide derivatives
;
_journal_issue                   10
_journal_name_full               'RSC Advances'
_journal_page_first              6494
_journal_page_last               6500
_journal_paper_doi               10.1039/D3RA08969J
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C30 H16 N2 O2 S, C30 H18 N2 O2 S'
_chemical_formula_sum            'C60 H34 N4 O4 S2'
_chemical_formula_weight         939.03
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-04-03 deposited with the CCDC.	2024-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                79.837(3)
_cell_angle_beta                 79.503(2)
_cell_angle_gamma                84.025(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3848(3)
_cell_length_b                   13.2196(5)
_cell_length_c                   19.2723(6)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      74.2900
_cell_measurement_theta_min      4.4520
_cell_volume                     2307.68(14)
_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      119.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_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    -52.00  29.00   1.00    4.03    --  -40.50  37.00 120.00   81
  2  \w   -119.00  -8.00   1.00    4.03    --  -40.50 -19.00 -60.00  111
  3  \w    -40.00  -9.00   1.00    4.03    --  -40.50 125.00-150.00   31
  4  \w     27.00  54.00   1.00    4.03    --   42.99-125.00 -90.00   27
  5  \w     39.00  68.00   1.00    4.03    --   42.99-125.00-180.00   29
  6  \w     39.00  98.00   1.00    4.03    --   42.99-125.00 -30.00   59
  7  \w     94.00 121.00   1.00   16.13    --  107.32-125.00   0.00   27
  8  \w     34.00 104.00   1.00   16.13    --  107.32 -77.00 -90.00   70
  9  \w     87.00 121.00   1.00   16.13    --  107.32-125.00-180.00   34
 10  \w     83.00 113.00   1.00   16.13    --  107.32  45.00-180.00   30
 11  \w    132.00 172.00   1.00   16.13    --  107.32  45.00-180.00   40
 12  \w     42.00  68.00   1.00   16.13    --  107.32-125.00   0.00   26
 13  \w     81.00 177.00   1.00   16.13    --  107.32  77.00 -30.00   96
 14  \w     87.00 171.00   1.00   16.13    --  107.32  30.00 120.00   84
 15  \w     33.00 139.00   1.00   16.13    --  107.32 -77.00   0.00  106
 16  \w     94.00 172.00   1.00   16.13    --  107.32 125.00   0.00   78
 17  \w     54.00 103.00   1.00   16.13    --  107.32 -94.00-180.00   49
 18  \w     80.00 172.00   1.00   16.13    --  107.32  61.00  60.00   92
 19  \w     36.00  81.00   1.00   16.13    --  107.32-125.00-180.00   45
;
_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      0.0208057000
_diffrn_orient_matrix_UB_12      -0.0547899000
_diffrn_orient_matrix_UB_13      0.0753330000
_diffrn_orient_matrix_UB_21      -0.0053508000
_diffrn_orient_matrix_UB_22      0.1053148000
_diffrn_orient_matrix_UB_23      0.0245289000
_diffrn_orient_matrix_UB_31      -0.1660294000
_diffrn_orient_matrix_UB_32      -0.0013604000
_diffrn_orient_matrix_UB_33      0.0225493000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16603
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.246
_diffrn_reflns_theta_min         3.821
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.496
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71936
_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    1.351
_exptl_crystal_description       needle
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.050
_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     631
_refine_ls_number_reflns         9130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.7650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8219
_reflns_number_total             9130
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra08969j2.cif
_cod_data_source_block           17061907
_cod_database_code               7248210
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHONS
_chemical_oxdiff_usercomment     PhMP2
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00O(H00O), C00U(H00U), C00V(H00V), C00Z(H00Z), C012(H012),
 C013(H013), C014(H014), C016(H016), C017(H017), C018(H018), C019(H019),
 C01A(H01A), C01B(H01B), C01D(H01D), C01E(H01E), C01F(H01F), C01H(H01H),
 C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N),
 C01O(H01O), C01P(H01P), C01Q(H01Q), C01S(H01S), C01T(H01T), C01U(H01U),
 C01V(H01V), C01W(H01W), C01X(H01X), C01Y(H01Y)
;
_shelx_res_checksum              68062
_shelx_hkl_checksum              99349
_shelx_fab_checksum              86677
_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 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.559