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_7248211
_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         'C36 H24 N2 O2'
_chemical_formula_sum            'C36 H24 N2 O2'
_chemical_formula_weight         516.57
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2019-01-05
_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                102.495(5)
_cell_angle_beta                 95.298(4)
_cell_angle_gamma                105.416(3)
_cell_formula_units_Z            6
_cell_length_a                   10.9035(4)
_cell_length_b                   16.1895(6)
_cell_length_c                   24.4187(17)
_cell_measurement_reflns_used    4738
_cell_measurement_temperature    291.7(6)
_cell_measurement_theta_max      74.3260
_cell_measurement_theta_min      3.8300
_cell_volume                     4005.2(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      air
_diffrn_ambient_temperature      291.7(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.946
_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    -92.00  -2.00   1.00   10.00    --  -41.14 125.00  60.00   90
  2  \w   -117.00 -12.00   1.00   10.00    --  -41.14 -77.00   0.00  105
  3  \w   -114.00 -14.00   1.00   10.00    --  -41.14 -57.00-120.00  100
  4  \w     29.00 109.00   1.00   30.00    --  109.40 -94.00  30.00   80
  5  \w     36.00 117.00   1.00   30.00    --  109.40-125.00 -30.00   81
  6  \w     94.00 177.00   1.00   30.00    --  109.40  30.00 150.00   83
  7  \w     39.00 117.00   1.00   30.00    --  109.40-125.00 -90.00   78
  8  \w     42.00 138.00   1.00   30.00    --  109.40 -61.00  60.00   96
  9  \w     59.00 174.00   1.00   30.00    --  109.40  15.00 -90.00  115
 10  \w    103.00 177.00   1.00   30.00    --  109.40 125.00  90.00   74
 11  \w     33.00 103.00   1.00   30.00    --  109.40 -30.00 -30.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1463020000
_diffrn_orient_matrix_UB_12      0.0389865000
_diffrn_orient_matrix_UB_13      0.0028287000
_diffrn_orient_matrix_UB_21      -0.0179973000
_diffrn_orient_matrix_UB_22      -0.0205273000
_diffrn_orient_matrix_UB_23      -0.0653487000
_diffrn_orient_matrix_UB_31      -0.0176436000
_diffrn_orient_matrix_UB_32      0.0919630000
_diffrn_orient_matrix_UB_33      0.0024293000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24159
_diffrn_reflns_point_group_measured_fraction_full 0.568
_diffrn_reflns_point_group_measured_fraction_max 0.541
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.902
_diffrn_reflns_theta_min         3.756
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       plate
_exptl_crystal_F_000             1620
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -1.0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.384
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2161
_refine_ls_number_reflns         17835
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.384
_refine_ls_R_factor_all          0.1625
_refine_ls_R_factor_gt           0.1377
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3838
_refine_ls_wR_factor_ref         0.4112
_reflns_Friedel_coverage         0.143
_reflns_Friedel_fraction_full    0.150
_reflns_Friedel_fraction_max     0.136
_reflns_number_gt                12059
_reflns_number_total             17835
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra08969j2.cif
_cod_data_source_block           19010209
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C216 H144 N12 O12'
_cod_original_formula_weight         3099.42
_cod_original_formula_moiety         '6(C36 H24 N2 O2)'
_cod_original_formula_units_Z            1
_cod_database_code               7248211
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     PhbITPA
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.884
_reflns_odcompleteness_completeness 98.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.46
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00G(H00G), C00L(H00L), C00P(H00P), C00X(H00X),
 C014(H014), C015(H015), C017(H017), C01A(H01A), C01C(H01C), C01E(H01E),
 C01F(H01F), C01G(H01G), C01H(H01H), C01I(H01I), C01K(H01K), C01L(H01L),
 C01N(H01N), C01O(H01O), C01S(H01S), C01T(H01T), C01U(H01U), C01V(H01V),
 C01Y(H01Y), C020(H020), C022(H022), C025(H025), C026(H026), C027(H027),
 C028(H028), C029(H029), C02D(H02D), C02F(H02F), C02H(H02H), C02I(H02I),
 C02L(H02L), C02N(H02N), C02O(H02O), C02R(H02R), C02S(H02S), C02W(H02W),
 C02Y(H02Y), C030(H030), C032(H032), C033(H033), C034(H034), C035(H035),
 C037(H037), C038(H038), C039(H039), C03A(H03A), C03B(H03B), C03C(H03C),
 C03E(H03E), C03F(H03F), C03G(H03G), C03I(H03I), C03K(H03K), C03L(H03L),
 C03M(H03M), C03Q(H03Q), C03S(H03S), C03T(H03T), C03X(H03X), C03Y(H03Y),
 C03Z(H03Z), C040(H040), C041(H041), C044(H044), C045(H045), C048(H048),
 C049(H049), C04B(H04B), C04C(H04C), C04F(H04F), C04G(H04G), C04H(H04H),
 C04I(H04I), C04J(H04J), C04K(H04K), C04L(H04L), C04M(H04M), C04N(H04N),
 C04O(H04O), C04P(H04P), C04Q(H04Q), C04R(H04R), C04S(H04S), C04U(H04U),
 C04X(H04X), C04Y(H04Y), C050(H050), C051(H051), C052(H052), C053(H053),
 C056(H056), C057(H057), C058(H058), C059(H059), C05A(H05A), C05B(H05B),
 C05C(H05C), C05D(H05D), C05E(H05E), C05F(H05F), C05H(H05H), C05I(H05I),
 C05J(H05J), C05K(H05K), C05L(H05L), C05M(H05M), C05N(H05N), C05O(H05O),
 C05P(H05P), C05R(H05R), C05S(H05S), C05T(H05T), C05U(H05U), C05W(H05W),
 C05Y(H05Y), C05Z(H05Z), C060(H060), C061(H061), C063(H063), C064(H064),
 C065(H065), C066(H066), C067(H067), C068(H068), C069(H069), C06A(H06A),
 C06D(H06D), C06E(H06E), C06F(H06F), C06G(H06G), C06H(H06H), C06I(H06I),
 C06J(H06J), C06K(H06K), C06L(H06L), C1(H1), C2(H2), C5(H5)
;
_shelx_res_checksum              97900
_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 3.821
_oxdiff_exptl_absorpt_empirical_full_min 0.531