Steric hindrance modulated efficient thermally activated delayed fluorescence with non-linear optical, ferroelectric and piezoelectric properties
Dutta, Madhusudan; Chatterjee, Abhijit; Deka, Nilotpal; Tanwar, Riteeka; Mishra, Vishnu; Saha, Arindam; Mandal, Pankaj; Boomishankar, Ramamoorthy; Hazra, Partha; Chemical Science 16 (2025) 11989–11998; doi:10.1039/D5SC02107C

data_1574734
_publ_section_title
;
 Steric hindrance modulated efficient thermally activated delayed
 fluorescence with non-linear optical, ferroelectric and piezoelectric
 properties
;
_journal_issue                   26
_journal_name_full               'Chemical Science'
_journal_page_first              11989
_journal_page_last               11998
_journal_paper_doi               10.1039/D5SC02107C
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C88 H50 N8'
_chemical_formula_sum            'C88 H50 N8'
_chemical_formula_weight         1219.431
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-08-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-01-28 deposited with the CCDC.	2025-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                66.243(2)
_cell_angle_beta                 67.979(2)
_cell_angle_gamma                89.261(2)
_cell_formula_units_Z            2
_cell_length_a                   16.2336(13)
_cell_length_b                   17.0377(12)
_cell_length_c                   17.1281(14)
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      2.43
_cell_volume                     3966.0(5)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_Laue_measured_fraction_full 0.9975
_diffrn_reflns_Laue_measured_fraction_max 0.9975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            82757
_diffrn_reflns_point_group_measured_fraction_full 0.9975
_diffrn_reflns_point_group_measured_fraction_max 0.9975
_diffrn_reflns_theta_full        24.9997
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1684 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.8013.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.021
_exptl_crystal_description       needle
_exptl_crystal_F_000             1268.712
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.4614
_refine_diff_density_min         -0.5046
_refine_diff_density_rms         0.0910
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             9.9086
_refine_ls_goodness_of_fit_ref   1.0879
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    121
_refine_ls_number_parameters     935
_refine_ls_number_reflns         13943
_refine_ls_number_restraints     234
_refine_ls_restrained_S_all      1.0783
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1199P)^2^+5.4461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2182
_refine_ls_wR_factor_ref         0.2445
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -17
_reflns_limit_k_max              20
_reflns_limit_k_min              -18
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                9906
_reflns_number_total             13943
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5sc02107c2.cif
_cod_data_source_block           mo_CZ2CZ_PhCl_0m_a
_cod_depositor_comments
'Adding full bibliography for 1574732--1574734.cif.'
_cod_database_code               1574734
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C16-N1A \\sim C16-N1b
 with sigma of 0.02
 C1A-C2A \\sim C1b-C2b
 with sigma of 0.02
 C1A-C6A \\sim C1b-C6b
 with sigma of 0.02
 C1A-N1A \\sim C1b-N1b
 with sigma of 0.02
 C2A-C3A \\sim C2b-C3b
 with sigma of 0.02
 C3A-C4A \\sim C3b-C4b
 with sigma of 0.02
 C4A-C5A \\sim C4b-C5b
 with sigma of 0.02
 C5A-C6A \\sim C5b-C6b
 with sigma of 0.02
 C6A-C7A \\sim C6b-C7b
 with sigma of 0.02
 C7A-C8A \\sim C7b-C8b
 with sigma of 0.02
 C7A-C12A \\sim C7b-C12b
 with sigma of 0.02
 C8A-C9A \\sim C8b-C9b
 with sigma of 0.02
 N1A-C12A \\sim N1b-C12b
 with sigma of 0.02
 C9A-C10A \\sim C9b-C10b
 with sigma of 0.02
 C10A-C11A \\sim C10b-C11b
 with sigma of 0.02
 C11A-C12A \\sim C11b-C12b
 with sigma of 0.02
 C16-C1A \\sim C16-C1b
 with sigma of 0.04
 C16-C12A \\sim C16-C12b
 with sigma of 0.04
 C1A-C3A \\sim C1b-C3b
 with sigma of 0.04
 C1A-C5A \\sim C1b-C5b
 with sigma of 0.04
 C1A-C7A \\sim C1b-C7b
 with sigma of 0.04
 C1A-C12A \\sim C1b-C12b
 with sigma of 0.04
 C2A-C4A \\sim C2b-C4b
 with sigma of 0.04
 C2A-C6A \\sim C2b-C6b
 with sigma of 0.04
 C2A-N1A \\sim C2b-N1b
 with sigma of 0.04
 C3A-C5A \\sim C3b-C5b
 with sigma of 0.04
 C4A-C6A \\sim C4b-C6b
 with sigma of 0.04
 C5A-C7A \\sim C5b-C7b
 with sigma of 0.04
 C6A-C8A \\sim C6b-C8b
 with sigma of 0.04
 C6A-N1A \\sim C6b-N1b
 with sigma of 0.04
 C6A-C12A \\sim C6b-C12b
 with sigma of 0.04
 C7A-N1A \\sim C7b-N1b
 with sigma of 0.04
 C7A-C9A \\sim C7b-C9b
 with sigma of 0.04
 C7A-C11A \\sim C7b-C11b
 with sigma of 0.04
 C8A-C10A \\sim C8b-C10b
 with sigma of 0.04
 C8A-C12A \\sim C8b-C12b
 with sigma of 0.04
 N1A-C11A \\sim N1b-C11b
 with sigma of 0.04
 C9A-C11A \\sim C9b-C11b
 with sigma of 0.04
 C10A-C12A \\sim C10b-C12b
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C4A)
\\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C7A) \\sim Ueq,
Uanis(C8A) \\sim Ueq, Uanis(N1A) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(C10A)
\\sim Ueq, Uanis(C11A) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(N1b) \\sim Ueq,
Uanis(C12b) \\sim Ueq, Uanis(C11b) \\sim Ueq, Uanis(C10b) \\sim Ueq, Uanis(C9b)
\\sim Ueq, Uanis(C8b) \\sim Ueq, Uanis(C7b) \\sim Ueq, Uanis(C6b) \\sim Ueq,
Uanis(C1b) \\sim Ueq, Uanis(C2b) \\sim Ueq, Uanis(C3b) \\sim Ueq, Uanis(C4b)
\\sim Ueq, Uanis(C5b) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.01
4. Others
 Sof(N1b)=Sof(C12b)=Sof(C11b)=Sof(C10b)=Sof(C9b)=Sof(C8b)=Sof(C7b)=Sof(C6b)=
 Sof(C1b)=Sof(C2b)=Sof(C3b)=Sof(C4b)=Sof(C5b)=Sof(H2b)=Sof(H3b)=Sof(H4b)=
 Sof(H5b)=Sof(H8b)=Sof(H9b)=Sof(H10b)=Sof(H11b)=1-FVAR(1)
 Sof(N1A)=Sof(C12A)=Sof(C11A)=Sof(C10A)=Sof(C9A)=Sof(C8A)=Sof(C7A)=Sof(C6A)=
 Sof(C1A)=Sof(C2A)=Sof(C3A)=Sof(C4A)=Sof(C5A)=Sof(H5A)=Sof(H4A)=Sof(H3A)=
 Sof(H2A)=Sof(H11A)=Sof(H10A)=Sof(H9A)=Sof(H8A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C42(H42), C40(H40), C41(H41), C33(H33), C34(H34), C31(H31), C60(H60),
 C58(H58), C57(H57), C64(H64), C63(H63), C61(H61), C20(H20), C21(H21), C17(H17),
  C29(H29), C28(H28), C26(H26), C81(H81), C82(H82), C83(H83), C84(H84),
 C88(H88), C87(H87), C86(H86), C85(H85), C73(H73), C74(H74), C75(H75), C76(H76),
  C201(H201), C79(H79), C78(H78), C77(H77), C5A(H5A), C4A(H4A), C3A(H3A),
 C2A(H2A), C11A(H11A), C10A(H10A), C9A(H9A), C8A(H8A), C2b(H2b), C3b(H3b),
 C4b(H4b), C5b(H5b), C8b(H8b), C9b(H9b), C10b(H10b), C11b(H11b), C45(H45),
 C46(H46), C47(H47), C48(H48), C52(H52), C51(H51), C50(H50), C49(H49)
5.b Fitted hexagon refined as free rotating group:
 C2A(C1A,C6A,C5A,C4A,C3A), C11A(C10A,C9A,C8A,C7A,C12A), C2b(C1b,C6b,C5b,C4b,
 C3b), C11b(C10b,C9b,C8b,C7b,C12b)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'