Eosin Y-catalyzed, visible-light-promoted carbophosphinylation of allylic alcohols via a radical neophyl rearrangement.
Yin, Yao; Weng, Wei-Zhi; Sun, Jian-Guo; Zhang, Bo; Organic & biomolecular chemistry 16 (2018) 2356–2361; doi:10.1039/C8OB00231B

data_7156145
_publ_section_title
;
 Eosin Y-catalyzed, visible-light-promoted carbophosphinylation of allylic
 alcohols via a radical neophyl rearrangement.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2356
_journal_page_last               2361
_journal_paper_doi               10.1039/C8OB00231B
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H25 O2 P'
_chemical_formula_weight         484.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1yt9pr
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-12-16 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.149(2)
_cell_length_b                   11.921(2)
_cell_length_c                   18.456(4)
_cell_measurement_reflns_used    4903
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.21
_cell_volume                     2452.9(8)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0369
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14706
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.034
_exptl_absorpt_coefficient_mu    0.142
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1557 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.42(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0841P)^2^+0.7332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1304
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3943
_reflns_number_total             4296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00231b2.cif
_cod_data_source_block           mo_20171213YKD_ZB_0m_a
_cod_depositor_comments          'Adding full bibliography for 7156145.cif.'
_cod_original_cell_volume        2452.8(9)
_cod_database_code               7156145
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              52745