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_7160397
_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 H25 O2 P'
_chemical_formula_sum            'C34 H25 O2 P'
_chemical_formula_weight         496.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-02-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-11-01 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.4030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.3029(2)
_cell_length_b                   26.9879(4)
_cell_length_c                   18.4734(3)
_cell_measurement_reflns_used    6208
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.95
_cell_measurement_theta_min      2.91
_cell_volume                     5104.55(15)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0563
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            61956
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.661
_diffrn_reflns_theta_min         2.911
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.185
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0967 before and 0.0730 after correction.
The Ratio of minimum to maximum transmission is 0.1193.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         10442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0797
_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^)+(0.1378P)^2^+0.1146P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1848
_refine_ls_wR_factor_ref         0.1984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8405
_reflns_number_total             10442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00061k2.cif
_cod_data_source_block           cu_0214_2_0m
_cod_depositor_comments
'Adding full bibliography for 7160396--7160397.cif.'
_cod_database_code               7160397
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.756
_shelx_estimated_absorpt_t_min   0.655
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C55(H55), C54(H54), C51(H51), C35(H35), C39(H39), C68(H68), C58(H58),
 C42(H42), C64(H64), C65(H65), C62(H62), C37(H37), C46(H46), C36(H36), C67(H67),
  C66(H66), C53(H53), C52(H52), C43(H43), C38(H38), C44(H44), C61(H61),
 C59(H59), C60(H60), C45(H45), C21(H21), C17(H17), C8(H8), C20(H20), C12(H12),
 C34(H34), C28(H28), C24(H24), C25(H25), C19(H19), C18(H18), C10(H10), C30(H30),
  C26(H26), C27(H27), C11(H11), C2(H2), C9(H9), C6(H6), C33(H33), C31(H31),
 C32(H32), C3(H3), C5(H5), C4(H4)
;
_shelx_res_checksum              9029
_olex2_submission_special_instructions 'No special instructions were received'