Ph3P-mediated highly selective C(α)–P coupling of quinone monoacetals with R2P(O)H: convenient and practical synthesis of ortho-phosphinyl phenols
Shen, Ruwei; Zhang, Ming; Xiao, Jing; Dong, Chao; Han, Li-Biao; Green Chemistry 20 (2018) 5111–; doi:10.1039/C8GC02918K

data_7237090
_publ_section_title
;
 Ph3P-mediated highly selective C(\a)--P coupling of quinone monoacetals
 with R2P(O)H: convenient and practical synthesis of ortho-phosphinyl
 phenols
;
_journal_issue                   22
_journal_name_full               'Green Chemistry'
_journal_page_first              5111
_journal_paper_doi               10.1039/C8GC02918K
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C19 H16 Br O3 P'
_chemical_formula_sum            'C19 H16 Br O3 P'
_chemical_formula_weight         403.20
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-28 deposited with the CCDC.
2018-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.026(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.870(3)
_cell_length_b                   8.1150(18)
_cell_length_c                   15.295(4)
_cell_measurement_reflns_used    2620
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.004
_cell_measurement_theta_min      1.425
_cell_volume                     1773.9(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12190
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.001
_diffrn_reflns_theta_max         25.001
_diffrn_reflns_theta_min         1.425
_exptl_absorpt_coefficient_mu    2.421
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.059
_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     217
_refine_ls_number_reflns         3127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0478P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0791
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2561
_reflns_number_total             3127
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc02918k2.cif
_cod_data_source_block           1
_cod_original_cell_volume        1773.8(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7237090
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              77552