Brønsted acid-mediated tandem cyclization of triarylphosphines and <i>in situ</i> generated <i>ortho</i>-alkynyl quinone methides: access to heterocyclic quaternary phosphonium salts.
Fan, Ya-Xin; Huang, Hong-Li; Su, Qing-Qiang; Lv, Yong-Zheng; Li, Shan; Ma, Yan-Hua; Mao, Yan-Xin; Ma, Chun-Lin; Du, Ji-Yuan; Chemical communications (Cambridge, England) 59 (2023) 3463–3466; doi:10.1039/d2cc06994f

data_7131326
_publ_section_title
;
 Br&#xf8;nsted acid-mediated tandem cyclization of triarylphosphines and
 <i>in situ</i> generated <i>ortho</i>-alkynyl quinone methides: access to
 heterocyclic quaternary phosphonium salts.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3463
_journal_page_last               3466
_journal_paper_doi               10.1039/d2cc06994f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_sum            'C34 H26 F3 O4 P S'
_chemical_formula_weight         618.58
_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_method           SHELXL-2018/3
_audit_update_record
;
2022-11-11 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                91.0520(10)
_cell_angle_beta                 92.132(3)
_cell_angle_gamma                90.8130(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3536(8)
_cell_length_b                   11.2590(9)
_cell_length_c                   14.7083(12)
_cell_measurement_reflns_used    3332
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.554
_cell_measurement_theta_min      3.282
_cell_volume                     1547.5(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7806
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.179
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.400
_exptl_transmission_factor_max   0.919
_exptl_transmission_factor_min   0.909
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0574
_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^)+(0.1012P)^2^+0.2212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1679
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3902
_reflns_number_total             5365
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06994f2.cif
_cod_data_source_block           220813c
_cod_depositor_comments
'Adding full bibliography for 7131326--7131327.cif.'
_cod_database_code               7131326
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.911
_shelx_estimated_absorpt_t_max   0.920
_shelx_res_checksum              66871
_shelx_hkl_checksum              64393