Excited-state intramolecular proton-transfer solid-state fluorophores with aggregation-induced emission as efficient emitters for electroluminescent devices
Petdee, Sujinda; Chantanop, Nuttapong; Arunlimsawat, Suangsiri; Saenubol, Atthapon; Nalaoh, Phattananawee; Sudyoadsuk, Taweesak; Promarak, Vinich; CrystEngComm 26 (2024) 4698–4707; doi:10.1039/D4CE00660G

data_7249180
_publ_section_title
;
 Excited-state intramolecular proton-transfer solid-state fluorophores
 with aggregation-induced emission as efficient emitters for
 electroluminescent devices
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              4698
_journal_page_last               4707
_journal_paper_doi               10.1039/D4CE00660G
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C41 H31 N3 O'
_chemical_formula_sum            'C41 H31 N3 O'
_chemical_formula_weight         581.69
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-02-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-10 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                106.157(5)
_cell_angle_beta                 97.582(5)
_cell_angle_gamma                98.728(6)
_cell_formula_units_Z            2
_cell_length_a                   10.6202(17)
_cell_length_b                   11.1341(18)
_cell_length_c                   13.581(2)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.30
_cell_volume                     1498.7(4)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            43101
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         1.943
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0992 before and 0.0695 after correction.
The Ratio of minimum to maximum transmission is 0.9324.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/methanol'
_exptl_crystal_size_max          0.339
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.216
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0247(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   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         6610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0410P)^2^+0.9057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5096
_reflns_number_total             6610
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00660g2.cif
_cod_data_source_block           vippn_nc02120
_cod_depositor_comments
'Adding full bibliography for 7249179--7249180.cif.'
_cod_database_code               7249180
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Others
 Fixed Sof: N3A(0.8) N3B(0.2) C31A(0.8) H31A(0.8) C31B(0.2) H31B(0.2)
 C32A(0.8) H32A(0.8) C32B(0.2) H32B(0.2) H34(0.8) H34A(0.2)
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C27(H27),
  C28(H28), C29(H29), C31A(H31A), C31B(H31B), C32A(H32A), C32B(H32B), C34(H34),
 C34(H34A), C35(H35), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42)
2.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C)
;
_shelx_res_checksum              80851
_shelx_hkl_checksum              90327
_olex2_submission_special_instructions 'No special instructions were received'