Phosphinylation/cyclization of propynolaldehydes to isobenzo-furanylic phosphine oxides displaying AIE properties.
Chang, Xin; Han, Xiao-Wen; Zhu, Hai-Tao; Zhou, Ni-Ni; Yang, Nan; Shen, Cheng-Ping; Qi, Chunxuan; Zhou, An-Xi; Feng, Hai-Tao; Tang, Ben Zhong; Organic & biomolecular chemistry 23 (2025) 3154–3162; doi:10.1039/d5ob00061k

data_7160396
_publ_section_title
;
 Phosphinylation/cyclization of propynolaldehydes to isobenzo-furanylic
 phosphine oxides displaying AIE properties.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3154
_journal_page_last               3162
_journal_paper_doi               10.1039/d5ob00061k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C34 H24 F O2 P, 1[]'
_chemical_formula_sum            'C34 H24 F O2 P'
_chemical_formula_weight         514.50
_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             2023-09-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-11-01 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                68.506(2)
_cell_angle_beta                 85.739(4)
_cell_angle_gamma                70.953(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3555(5)
_cell_length_b                   11.2209(8)
_cell_length_c                   14.2183(8)
_cell_measurement_reflns_used    4715
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      56.888
_cell_measurement_theta_min      2.908
_cell_volume                     1311.02(14)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15171
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_min         1.541
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1859 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.8466.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5286
_refine_ls_number_restraints     122
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0515P)^2^+0.2913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4249
_reflns_number_total             5286
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00061k2.cif
_cod_data_source_block           1_sq
_cod_depositor_comments
'Adding full bibliography for 7160396--7160397.cif.'
_cod_database_code               7160396
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 P1-C23 = P1-C39
 1.9 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C23 \\sim C28 \\sim C27 \\sim C26 \\sim C25 \\sim C24 \\sim P1 \\sim O2: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C28, C27, C26, C25, C24, C23, C40, C37, C36, C35, C38, C39
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C40)=Sof(H40)=Sof(C37)=Sof(H37)=Sof(C36)=Sof(H36)=Sof(C35)=Sof(H35)=
 Sof(C38)=Sof(H38)=Sof(C39)=1-FVAR(1)
 Sof(C23)=Sof(C28)=Sof(H28)=Sof(C27)=Sof(H27)=Sof(C26)=Sof(H26)=Sof(C25)=
 Sof(H25)=Sof(C24)=Sof(H24)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C28(H28), C27(H27),
  C26(H26), C25(H25), C24(H24), C30(H30), C31(H31), C32(H32), C33(H33),
 C34(H34), C40(H40), C37(H37), C36(H36), C35(H35), C38(H38)
6.b Fitted hexagon refined as free rotating group:
 C23(C28,C27,C26,C25,C24), C40(C37,C36,C35,C38,C39)
;
_shelx_res_checksum              42977
_shelx_fab_checksum              64153
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'