Access to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed Desymmetrization of Bisphenols.
Huang, Zhijian; Huang, Xuan; Li, Baosheng; Mou, Chengli; Yang, Song; Song, Bao-An; Chi, Yonggui Robin; Journal of the American Chemical Society 138 (2016) 7524–7527; doi:10.1021/jacs.6b04624

data_4130559
_publ_section_title
;
 Access to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed
 Desymmetrization of Bisphenols.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7524
_journal_page_last               7527
_journal_paper_doi               10.1021/jacs.6b04624
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H21 Br2 O6 P'
_chemical_formula_weight         620.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90.528(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7211(9)
_cell_length_b                   7.1449(4)
_cell_length_c                   23.5913(14)
_cell_measurement_reflns_used    1881
_cell_measurement_temperature    153.(2)
_cell_measurement_theta_max      19.5936
_cell_measurement_theta_min      2.7674
_cell_volume                     2481.2(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2014)'
_diffrn_ambient_temperature      153.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1409
_diffrn_reflns_number            7017
_diffrn_reflns_theta_full        29.75
_diffrn_reflns_theta_max         29.75
_diffrn_reflns_theta_min         1.73
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.372
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.654
_refine_ls_abs_structure_details
;
Flack x determined using 1258 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         7017
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0673P)^2^+0.8350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1711
_reflns_number_gt                4039
_reflns_number_total             7017
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b04624_si_001.cif
_cod_data_source_block           I
_cod_database_code               4130559
_shelx_res_checksum              61328
_shelx_hkl_checksum              10462