Multiple-resonance thermally activated delayed fluorescence materials based on phosphorus central chirality for efficient circularly polarized electroluminescence
Wang, Yu; Lv, Zi-Yi; Chen, Zi-Xuan; Xing, Shuai; Huo, Zhong-Zhong; Hong, Xian-Fang; Yuan, Li; Li, Wei; Zheng, You-Xuan; Materials Horizons 11 (2024) 4722–4729; doi:10.1039/D4MH00605D

data_1572049
_publ_section_title
;
 Multiple-resonance thermally activated delayed fluorescence materials
 based on phosphorus central chirality for efficient circularly polarized
 electroluminescence
;
_journal_issue                   19
_journal_name_full               'Materials Horizons'
_journal_page_first              4722
_journal_page_last               4729
_journal_paper_doi               10.1039/D4MH00605D
_journal_volume                  11
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety
'C64 H60 B N2 O P, 4[CH2Cl2], 1[CH3OH], 0.333[], 0.417[], 0.167[]'
_chemical_formula_sum            'C69 H72 B Cl8 N2 O2 P'
_chemical_formula_weight         1286.66
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-01 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            12
_cell_length_a                   32.7114(13)
_cell_length_b                   32.7114(13)
_cell_length_c                   23.7266(14)
_cell_measurement_reflns_used    9373
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      45.244
_cell_measurement_theta_min      2.700
_cell_volume                     21986.9(18)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0948
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            147656
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.714
_diffrn_reflns_theta_min         3.120
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.332
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1198 before and 0.0789 after correction.
The Ratio of minimum to maximum transmission is 0.7064.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             8064
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 5252 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.091(13)
_refine_ls_extinction_coef       0.00063(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1312
_refine_ls_number_reflns         25876
_refine_ls_number_restraints     1572
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0827
_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^)+(0.1888P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2313
_refine_ls_wR_factor_ref         0.2824
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                15296
_reflns_number_total             25876
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4mh00605d2.cif
_cod_data_source_block           a_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1572048--1572049.cif.
;
_cod_original_cell_volume        21987(2)
_cod_database_code               1572049
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.732
_shelx_estimated_absorpt_t_min   0.671
_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. Restrained distances
 C1A-C125 \\sim C128-C125 \\sim C1B-C125 \\sim C126-C125 \\sim C130-C125 \\sim
C127-C125
 with sigma of 0.02
 C98A-C97 \\sim C98-C97 \\sim C97-C129 \\sim C97-C100 \\sim C99A-C97 \\sim
C99-C97
 with sigma of 0.02
 C99-C98 \\sim C98-C100 \\sim C99-C100 \\sim C99A-C98A \\sim C99A-C129 \\sim
C98A-C129
 with sigma of 0.02
 C128-C126 \\sim C127-C126 \\sim C128-C127 \\sim C1B-C130 \\sim C1A-C130 \\sim
C1B-C1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C97 \\sim C98 \\sim C100 \\sim C99 \\sim C98A \\sim C129 \\sim C99A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C125 \\sim C126 \\sim C128 \\sim C127 \\sim C130 \\sim C1A \\sim C1B: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C69 \\sim C68 \\sim C67 \\sim C66 \\sim C65 \\sim C70: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C98A)=Sof(H98D)=Sof(H98E)=Sof(H98F)=Sof(C129)=Sof(H12S)=Sof(H12T)=
 Sof(H12U)=Sof(C99A)=Sof(H99D)=Sof(H99E)=Sof(H99F)=1-FVAR(1)
 Sof(C98)=Sof(H98A)=Sof(H98B)=Sof(H98C)=Sof(C100)=Sof(H10J)=Sof(H10K)=
 Sof(H10L)=Sof(C99)=Sof(H99A)=Sof(H99B)=Sof(H99C)=FVAR(1)
 Sof(C130)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=
 Sof(H1AC)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=1-FVAR(2)
 Sof(C126)=Sof(H12J)=Sof(H12K)=Sof(H12L)=Sof(C128)=Sof(H12M)=Sof(H12N)=
 Sof(H12O)=Sof(C127)=Sof(H12P)=Sof(H12Q)=Sof(H12R)=FVAR(2)
6.a Riding coordinates:
 C18(H18), C22(H22), C80(H80), C52(H52), C84(H84), C40(H40), C117(H117),
 C123(H12G,H12H,H12I), C104(H104), C98A(H98D,H98E,H98F), C129(H12S,H12T,H12U),
 C99A(H99D,H99E,H99F), C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)
6.b Aromatic/amide H refined with riding coordinates:
 C74(H74), C75(H75), C77(H77), C32(H32), C37(H37), C2(H2), C23(H23), C58(H58),
 C118(H118), C24(H24), C9(H9), C39(H39), C60(H60), C94(H94), C49(H49), C96(H96),
  C112(H112), C30(H30), C85(H85), C110(H110), C51(H51), C3(H3), C88(H88),
 C15(H15), C87(H87), C86(H86), C4(H4), C103(H103), C6(H6), C120(H120), C10(H10),
  C11(H11), C12(H12), C70(H70), C66(H66), C67(H67), C68(H68), C69(H69), C5(H5),
 C101(H101)
6.c Fitted hexagon refined as free rotating group:
 C70(C65,C66,C67,C68,C69)
6.d Idealised Me refined as rotating group:
 C55(H55A,H55B,H55C), C57(H57A,H57B,H57C), C42(H42A,H42B,H42C), C106(H10A,H10B,
 H10C), C44(H44A,H44B,H44C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C),
 C122(H12A,H12B,H12C), C35(H35A,H35B,H35C), C43(H43A,H43B,H43C), C108(H10D,H10E,
 H10F), C56(H56A,H56B,H56C), C107(H10G,H10H,H10I), C124(H12D,H12E,H12F),
 C62(H62A,H62B,H62C), C64(H64A,H64B,H64C), C98(H98A,H98B,H98C), C100(H10J,H10K,
 H10L), C63(H63A,H63B,H63C), C126(H12J,H12K,H12L), C99(H99A,H99B,H99C),
 C128(H12M,H12N,H12O), C127(H12P,H12Q,H12R), C130(H13A,H13B,H13C)
;
_shelx_res_checksum              71827
_shelx_hkl_checksum              941
_shelx_fab_checksum              36311
_platon_squeeze_special_details
;
A solvent mask was calculated and 2191 electrons were 
found in a volume of 9401\%A^3^ in 4 voids per unit cell. 
This is consistent with the presence of 
4[CH2Cl2], 1[CH3OH], per formula unit 
which account for 2232 electrons 
per unit cell.
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU