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_4034618
_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_moiety         'C27 H20 F O2 P'
_chemical_formula_sum            'C27 H20 F O2 P'
_chemical_formula_weight         426.40
_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   mixed
_audit_creation_date             2018-11-22
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_cell_angle_alpha                75.545(6)
_cell_angle_beta                 84.220(7)
_cell_angle_gamma                76.423(7)
_cell_formula_units_Z            2
_cell_length_a                   9.395(3)
_cell_length_b                   10.610(3)
_cell_length_c                   11.090(4)
_cell_measurement_reflns_used    2063
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.16
_cell_measurement_theta_min      2.43
_cell_volume                     1039.5(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_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_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8478
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.898
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.1307 before and 0.0532 after correction. 
The Ratio of minimum to maximum transmission is 0.8189. 
The \l/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0332P)^2^+0.3252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2397
_reflns_number_total             3630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00570_si_002.cif
_cod_data_source_block           mo_181122a_0m
_cod_database_code               4034618
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.968
_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 
 C4-F1 = C10-F1' 
 1.38 with sigma of 0.01 
 C10-C27 = C4-C27' 
 1.48 with sigma of 0.01 
 C27'-C3 \\sim C27'-C5 
 with sigma of 0.01 
3. Restrained planarity 
 C1, C2, C3, C4, C5, C6, C27' 
 with sigma of 0.1 
4. Uiso/Uaniso restraints and constraints 
Uanis(F1) = Uanis(C27') 
Uanis(C27) = Uanis(F1') 
5. Others 
 Sof(C27')=Sof(H27D)=Sof(H27E)=Sof(H27F)=Sof(F1')=1-FVAR(1) 
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(F1)=FVAR(1) 
6.a Riding coordinates: 
 C27(H27A,H27B,H27C), C27'(H27D,H27E,H27F) 
6.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C17(H17), 
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26) 
;
_olex2_submission_special_instructions 'No special instructions were received'