Photoredox/Cobalt-Catalyzed Phosphinyloxy Radical Addition/Cyclization Cascade: Synthesis of Phosphaisocoumarins.
Qiao, Ming-Ming; Liu, Yi-Yin; Yao, Sheng; Ma, Tian-Cong; Tang, Zi-Long; Shi, De-Qing; Xiao, Wen-Jing; The Journal of organic chemistry 84 (2019) 6798–6806; doi:10.1021/acs.joc.9b00570

data_4034617
_publ_section_title
;
 Photoredox/Cobalt-Catalyzed Phosphinyloxy Radical Addition/Cyclization
 Cascade: Synthesis of Phosphaisocoumarins.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6798
_journal_page_last               6806
_journal_paper_doi               10.1021/acs.joc.9b00570
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C26 H19 O2 P'
_chemical_formula_weight         394.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.091(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.835(4)
_cell_length_b                   10.618(5)
_cell_length_c                   21.406(10)
_cell_measurement_reflns_used    980
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      2.44
_cell_volume                     2003.0(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.1045
_diffrn_reflns_av_unetI/netI     0.0967
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13409
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        24.975
_diffrn_reflns_theta_max         24.975
_diffrn_reflns_theta_min         1.908
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0463P)^2^+0.5041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1500
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1902
_reflns_number_total             3443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00570_si_001.cif
_cod_data_source_block           mo_180530B_0m
_cod_original_cell_volume        2003.1(16)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034617
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              4704
_shelx_hkl_checksum              51149