An extended π-backbone for highly efficient near-infrared thermally activated delayed fluorescence with enhanced horizontal molecular orientation.
He, Jian-Li; Tang, Yukun; Zhang, Kai; Zhao, Yue; Lin, Yu-Ching; Hsu, Chih-Kai; Chen, Chia-Hsun; Chiu, Tien-Lung; Lee, Jiun-Haw; Wang, Chuan-Kui; Wu, Chung-Chih; Fan, Jian; Materials horizons 9 (2022) 772–779; doi:10.1039/d1mh01651b

data_1565433
_publ_section_title
;
 An extended \p-backbone for highly efficient near-infrared thermally
 activated delayed fluorescence with enhanced horizontal molecular
 orientation.
;
_journal_issue                   2
_journal_name_full               'Materials horizons'
_journal_page_first              772
_journal_page_last               779
_journal_paper_doi               10.1039/d1mh01651b
_journal_volume                  9
_journal_year                    2022
_chemical_formula_moiety         '3(C H Cl3), C45 H38 N6'
_chemical_formula_sum            'C48 H41 Cl9 N6'
_chemical_formula_weight         1020.92
_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             2021-01-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-05-13 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                83.9310(10)
_cell_angle_beta                 83.1430(10)
_cell_angle_gamma                86.2090(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1464(3)
_cell_length_b                   11.8837(4)
_cell_length_c                   25.5753(9)
_cell_measurement_reflns_used    6160
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.300
_cell_measurement_theta_min      2.475
_cell_volume                     2440.85(15)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            22953
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.565
_diffrn_reflns_theta_min         2.242
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1455 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.8637.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.954
_refine_diff_density_min         -0.961
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     636
_refine_ls_number_reflns         11104
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0813
_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^)+(0.0998P)^2^+2.8471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2098
_refine_ls_wR_factor_ref         0.2512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6562
_reflns_number_total             11104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1mh01651b2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 1565433.cif.'
_cod_database_code               1565433
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.936
_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. Rigid body (RIGU) restrains
 C1, C3, C2, C4, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C3A, C2A, C1A, C4, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C14, C17, C20A, C18A, C19A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C14, C17, C20, C18, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1, C3, C2, C20, C19, C18, C17, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=
 Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(1)
 Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C18A)=Sof(H18D)=Sof(H18E)=
 Sof(H18F)=Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=1-FVAR(2)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C47(H47), C49(H49), C48(H48)
4.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C25(H25), C15(H15), C26(H26), C38(H38), C31(H31), C12(H12),
 C22(H22), C6(H6), C23(H23), C28(H28), C7(H7), C9(H9), C37(H37), C10(H10),
 C44(H44), C39(H39), C45(H45), C46(H46), C40(H40)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C2(H2A,H2B,H2C),
 C3(H3A,H3B,H3C), C19(H19A,H19B,H19C), C3A(H3AA,H3AB,H3AC), C1A(H1AA,H1AB,H1AC),
  C2A(H2AA,H2AB,H2AC), C20A(H20D,H20E,H20F), C18A(H18D,H18E,H18F), C19A(H19D,
 H19E,H19F)
;
_shelx_res_checksum              25364
_olex2_submission_special_instructions 'No special instructions were received'