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_1572048
_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 syn
_chemical_formula_moiety         '0.5(C H2 Cl2), C58 H57 B N O2 P, 1.5[CH3OH]'
_chemical_formula_sum            'C60 H64 B Cl N O3.5 P'
_chemical_formula_weight         932.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2jpj1t
_audit_creation_date             2024-06-17
_audit_creation_method
;
Olex2 1.5-beta
(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                 92.763(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2454(13)
_cell_length_b                   19.524(3)
_cell_length_c                   29.571(6)
_cell_measurement_reflns_used    683
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      61.05
_cell_measurement_theta_min      28.28
_cell_volume                     5331.6(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1212
_diffrn_reflns_av_unetI/netI     0.1040
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            84149
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         88.583
_diffrn_reflns_theta_min         2.713
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.263
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1323 before and 0.0708 after correction.
The Ratio of minimum to maximum transmission is 0.8388.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 3665 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.060(13)
_refine_ls_extinction_coef       0.0063(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1342
_refine_ls_number_reflns         20432
_refine_ls_number_restraints     479
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.0923
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1726P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2425
_refine_ls_wR_factor_ref         0.2883
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                11084
_reflns_number_total             20432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4mh00605d2.cif
_cod_data_source_block           p21
_cod_depositor_comments
'Adding full bibliography for 1572048--1572049.cif.'
_cod_original_cell_volume        5331.5(15)
_cod_original_formula_sum        'C60 H64 B Cl N O3.50 P'
_cod_database_code               1572048
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.863
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C99-C1C = C99-C102 = C99-C118 = C99-C100 = C99-C101 = C99-C1D = C116-C113 =
 C117-C113 = C114-C113 = C1B-C113 = C115-C113 = C1A-C113
 1.54 with sigma of 0.002
 Cl3-C03U = Cl4-C03U
 1.8 with sigma of 0.01
 H20-H44
 2 with sigma of 0.01
 C49-C48 = C50-C48 = C50A-C48 = C51A-C48 = C51-C48 = C49A-C48 = C36-C35 = C37A-
 C35 = C36A-C35 = C38-C35 = C38A-C35 = C37-C35
 1.54 with sigma of 0.001
 C56-C55 = C56A-C55 = C57A-C55 = C57-C55 = C58-C55 = C58A-C55 = C33-C31 = C32-
 C31 = C34-C31
 1.54 with sigma of 0.001
 C90-C89 = C91-C89 = C92-C89
 1.54 with sigma of 0.001
 Cl3-Cl4
 2.8 with sigma of 0.01
 C38A-C35 \\sim C38-C35 \\sim C36A-C35 \\sim C36-C35 \\sim C37-C35 \\sim
C37A-C35
 with sigma of 0.02
 C99-C1D \\sim C99-C101 \\sim C99-C1C \\sim C99-C102 \\sim C99-C118 \\sim
C99-C100
 with sigma of 0.02
 Cl2-C03R \\sim Cl1-C03R
 with sigma of 0.02
 C1A-C113 \\sim C116-C113 \\sim C117-C113 \\sim C114-C113 \\sim C1B-C113 \\sim
C115-C113
 with sigma of 0.02
 C115-C114 \\sim C116-C115 \\sim C116-C114 \\sim C1A-C117 \\sim C1B-C117 \\sim
C1B-C1A
 with sigma of 0.02
 C57-C55 \\sim C58A-C55 \\sim C58-C55 \\sim C56A-C55 \\sim C56-C55 \\sim
C57A-C55
 with sigma of 0.02
 C51-C48 \\sim C51A-C48 \\sim C50-C48 \\sim C50A-C48 \\sim C49-C48 \\sim
C49A-C48
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1C \\sim C1D \\sim C99 \\sim C100 \\sim C101 \\sim C102 \\sim C118: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C35 \\sim C36 \\sim C37 \\sim C38 \\sim C36A \\sim C37A \\sim C38A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Cl3 \\sim Cl4 \\sim C03U: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C1A \\sim C1B \\sim C113 \\sim C114 \\sim C115 \\sim C116 \\sim C117: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C55 \\sim C56 \\sim C56A \\sim C57 \\sim C57A \\sim C58 \\sim C58A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C48 \\sim C49 \\sim C50 \\sim C51 \\sim C51A \\sim C50A \\sim C49A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=
 Sof(C117)=Sof(H11S)=Sof(H11T)=Sof(H11U)=1-FVAR(1)
 Sof(C114)=Sof(H11J)=Sof(H11K)=Sof(H11L)=Sof(C115)=Sof(H11M)=Sof(H11N)=
 Sof(H11O)=Sof(C116)=Sof(H11P)=Sof(H11Q)=Sof(H11R)=FVAR(1)
 Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=
 Sof(C118)=Sof(H11V)=Sof(H11W)=Sof(H11X)=1-FVAR(2)
 Sof(C100)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C101)=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=Sof(C102)=Sof(H10G)=Sof(H10H)=Sof(H10I)=FVAR(2)
 Sof(C56A)=Sof(H56D)=Sof(H56E)=Sof(H56F)=Sof(C57A)=Sof(H57D)=Sof(H57E)=
 Sof(H57F)=Sof(C58A)=Sof(H58D)=Sof(H58E)=Sof(H58F)=1-FVAR(3)
 Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(H56C)=Sof(C57)=Sof(H57A)=Sof(H57B)=Sof(H57C)=
 Sof(C58)=Sof(H58A)=Sof(H58B)=Sof(H58C)=FVAR(3)
 Sof(C36A)=Sof(H36D)=Sof(H36E)=Sof(H36F)=Sof(C37A)=Sof(H37D)=Sof(H37E)=
 Sof(H37F)=Sof(C38A)=Sof(H38D)=Sof(H38E)=Sof(H38F)=1-FVAR(4)
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=FVAR(4)
 Sof(C51A)=Sof(H51D)=Sof(H51E)=Sof(H51F)=Sof(C50A)=Sof(H50D)=Sof(H50E)=
 Sof(H50F)=Sof(C49A)=Sof(H49D)=Sof(H49E)=Sof(H49F)=1-FVAR(5)
 Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(H49C)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(H50C)=
 Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=FVAR(5)
 Fixed Sof: Cl1(0.5) Cl2(0.5) C03R(0.5) H03A(0.5) H03B(0.5) Cl3(0.5) Cl4(0.5)
 C03U(0.5) H03C(0.5) H03D(0.5)
 Fixed Y: P2(0.70721)
5.a Riding coordinates:
 C102(H10G,H10H,H10I), C36A(H36D,H36E,H36F)
5.b Secondary CH2 refined with riding coordinates:
 C03R(H03A,H03B), C03U(H03C,H03D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C15(H15), C17(H17), C20(H20), C24(H24), C27(H27), C29(H29), C44(H44),
  C45(H45), C47(H47), C52(H52), C54(H54), C64(H64), C63(H63), C62(H62),
 C61(H61), C60(H60), C67(H67), C68(H68), C69(H69), C70(H70), C72(H72), C73(H73),
  C75(H75), C78(H78), C82(H82), C85(H85), C87(H87), C88(H88), C94(H94),
 C96(H96), C104(H104), C106(H106)
5.d Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6), C59(C64,C63,C62,C61,C60)
5.e Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C49(H49A,H49B,H49C), C50(H50A,
 H50B,H50C), C51(H51A,H51B,H51C), C56(H56A,H56B,H56C), C56A(H56D,H56E,H56F),
 C57(H57A,H57B,H57C), C57A(H57D,H57E,H57F), C58(H58A,H58B,H58C), C58A(H58D,H58E,
 H58F), C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC), C1C(H1CA,H1CB,H1CC), C1D(H1DA,
 H1DB,H1DC), C90(H90A,H90B,H90C), C91(H91A,H91B,H91C), C92(H92A,H92B,H92C),
 C100(H10A,H10B,H10C), C101(H10D,H10E,H10F), C110(H11A,H11B,H11C), C111(H11D,
 H11E,H11F), C112(H11G,H11H,H11I), C114(H11J,H11K,H11L), C115(H11M,H11N,H11O),
 C116(H11P,H11Q,H11R), C117(H11S,H11T,H11U), C118(H11V,H11W,H11X), C37A(H37D,
 H37E,H37F), C38A(H38D,H38E,H38F), C51A(H51D,H51E,H51F), C50A(H50D,H50E,H50F),
 C49A(H49D,H49E,H49F)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 105 electrons were 
found in a volume of 455\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1.5[CH3OH] per formula unit 
which account for 108 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              58094
_shelx_hkl_checksum              97068
_shelx_fab_checksum              43211
_olex2_submission_special_instructions 'No special instructions were received'