Phenphosphine-X(O, S, Se) locking multi-resonance thermally activated delayed fluorescence materials.
Hong, Xian-Fang; Wei, Yi; Xing, Hao-Ran; Wang, Yu; Xi, Jia-Qi; Wu, Chen-Yang; Yuan, Li; Li, Cheng-Hui; Zheng, You-Xuan; Chemical science 17 (2026) 274–282; doi:10.1039/d5sc06565h

data_1576186
_publ_section_title
;
 Phenphosphine-X(O, S, Se) locking multi-resonance thermally activated
 delayed fluorescence materials.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              274
_journal_page_last               282
_journal_paper_doi               10.1039/d5sc06565h
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C52 H52 B N2 O P, 1[C7H8]'
_chemical_formula_sum            'C59 H60 B N2 O P'
_chemical_formula_weight         854.87
_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
_audit_creation_date             2025-02-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-20 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                92.727(5)
_cell_angle_beta                 97.742(5)
_cell_angle_gamma                99.273(5)
_cell_formula_units_Z            2
_cell_length_a                   10.7415(19)
_cell_length_b                   13.639(3)
_cell_length_c                   16.481(3)
_cell_measurement_reflns_used    2846
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      24.24
_cell_measurement_theta_min      2.25
_cell_volume                     2355.3(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1586
_diffrn_reflns_av_unetI/netI     0.1723
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15755
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.896
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.015(3)
_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   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     620
_refine_ls_number_reflns         8230
_refine_ls_number_restraints     234
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1995
_refine_ls_R_factor_gt           0.1191
_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^)+(0.1034P)^2^+6.3320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2822
_refine_ls_wR_factor_ref         0.3333
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4087
_reflns_number_total             8230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06565h2.cif
_cod_data_source_block           0215_sq
_cod_depositor_comments
'Adding full bibliography for 1576185--1576187.cif.'
_cod_database_code               1576186
_shelx_shelxl_version_number     2018/3
_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
 H00Y-H013
 1.98 with sigma of 0.001
 P001-C00T \\sim P001-C3
 with sigma of 0.02
 C00T-C01E \\sim C3-C01F
 with sigma of 0.02
 C00T-C01B \\sim C3-C5
 with sigma of 0.02
 C01B-C4 \\sim C5-C4A
 with sigma of 0.02
 C4-C1 \\sim C4A-C1A
 with sigma of 0.02
 C00T-C4 \\sim C3-C4A
 with sigma of 0.04
 C1-C2 \\sim C1A-C2A
 with sigma of 0.02
 P001-C01B \\sim P001-C5
 with sigma of 0.04
 C00T-C2 \\sim C3-C2A
 with sigma of 0.04
 C2-C01E \\sim C2A-C01F
 with sigma of 0.02
 C01B-C1 \\sim C5-C1A
 with sigma of 0.04
 P001-C01E \\sim P001-C01F
 with sigma of 0.04
 C01B-C01E \\sim C5-C01F
 with sigma of 0.04
 C4-C2 \\sim C4A-C2A
 with sigma of 0.04
 C1-C01E \\sim C1A-C01F
 with sigma of 0.04
 C015-C01H \\sim C015-C16
 with sigma of 0.02
 C015-C01I \\sim C015-C17
 with sigma of 0.02
 C015-C01J \\sim C015-C01K
 with sigma of 0.02
 C01I-C01H \\sim C01J-C17 \\sim C16-C01K
 with sigma of 0.02
 C00U-C7 \\sim C00U-C7A
 with sigma of 0.02
 C00U-C8 \\sim C00U-C8A
 with sigma of 0.02
 C00U-C6 \\sim C00U-C6A
 with sigma of 0.02
 C7-C6 \\sim C8-C7A \\sim C6A-C8A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C00U \\sim C00D: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C00U \\sim C7 \\sim C8 \\sim C6 \\sim C6A \\sim C8A \\sim C7A \\sim C00D:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C3 \\sim P001: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C17 \\sim C01J \\sim C015: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C2 \\sim C1 \\sim C4 \\sim C01B \\sim C00T \\sim C01E: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C00T, C01B, C4, C1, C2, C01E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3, C5, C4A, C1A, C2A, C01F
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C01H, C01I, C01J
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16, C17, C01K
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C8, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7A, C8A, C6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C3)=Sof(C5)=Sof(H5)=Sof(C4A)=Sof(H4A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=
 Sof(C01F)=Sof(H01)=1-FVAR(1)
 Sof(C00T)=Sof(C01B)=Sof(H01B)=Sof(C4)=Sof(H4)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=
 Sof(C01E)=Sof(H01E)=FVAR(1)
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 Sof(C01K)=Sof(H3)=Sof(HC)=Sof(HD)=1-FVAR(2)
 Sof(C01H)=Sof(H01U)=Sof(H01V)=Sof(H01W)=Sof(C01I)=Sof(H01X)=Sof(H01Y)=Sof(H)=
 Sof(C01J)=Sof(H01Z)=Sof(HA)=Sof(HB)=FVAR(2)
 Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=
 Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=1-FVAR(3)
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C6)=
 Sof(H6A)=Sof(H6B)=Sof(H6C)=FVAR(3)
6.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00H(H00H), C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R),
 C01B(H01B), C4(H4), C1(H1), C2(H2), C01E(H01E), C00W(H00W), C00Y(H00Y),
 C00Z(H00Z), C012(H012), C013(H013), C5(H5), C4A(H4A), C1A(H1A), C2A(H2A),
 C01F(H01)
6.b Fitted hexagon refined as free rotating group:
 C00T(C01B,C4,C1,C2,C01E), C3(C5,C4A,C1A,C2A,C01F)
6.c Idealised Me refined as rotating group:
 C011(H01A,H01C,H01D), C014(H01F,H01G,H01H), C016(H01I,H01J,H01K), C017(H01L,
 H01M,H01N), C018(H01O,H01P,H01Q), C019(H01R,H01S,H01T), C01H(H01U,H01V,H01W),
 C01I(H01X,H01Y,H), C01J(H01Z,HA,HB), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C),
 C01K(H3,HC,HD), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C6(H6A,H6B,H6C), C6A(H6AA,
 H6AB,H6AC), C8A(H8AA,H8AB,H8AC), C7A(H7AA,H7AB,H7AC)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 85 electrons were 
found in a volume of 413\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1[C7H8] toluene per formula unit 
which account for 100 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              84856
_shelx_fab_checksum              72580
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'