Asymmetric synthesis of p-stereogenic diarylphosphinites by palladium-catalyzed enantioselective addition of diarylphosphines to benzoquinones.
Huang, Yinhua; Li, Yongxin; Leung, Pak-Hing; Hayashi, Tamio; Journal of the American Chemical Society 136 (2014) 4865–4868; doi:10.1021/ja501007t

data_4121628
_publ_section_title
;
 Asymmetric synthesis of p-stereogenic diarylphosphinites by
 palladium-catalyzed enantioselective addition of diarylphosphines to
 benzoquinones.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4865
_journal_page_last               4868
_journal_paper_doi               10.1021/ja501007t
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C48.5 H48 Cl4 N O2 P Pd'
_chemical_formula_weight         956.05
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3208(10)
_cell_length_b                   35.000(3)
_cell_length_c                   10.4586(8)
_cell_measurement_reflns_used    9249
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      30.18
_cell_measurement_theta_min      2.33
_cell_volume                     4510.0(6)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            41191
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         1.16
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  0.9055
_exptl_absorpt_correction_T_min  0.7607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1964
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.827
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.267
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         13755
_refine_ls_number_restraints     130
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0951P)^2^+5.4287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.1782
_reflns_number_gt                11978
_reflns_number_total             13755
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja501007t_si_004.cif
_cod_data_source_block           leung711s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2
_cod_original_formula_sum        'C48.50 H48 Cl4 N O2 P Pd'
_cod_database_code               4121628