Synthesis of Biaryl Diphosphines via a Stepwise Regioselective Double Diels−Alder Cycloaddition−Elimination Sequence: Efficient Ligands for the Palladium-Catalyzed Amination of Aromatic Bromides
Doherty, Simon; Smyth, Catherine H.; Harrington, Ross W.; Clegg, William; Organometallics 28 (2009) 5273–; doi:10.1021/om9004862

data_4069892
_publ_section_title
;
 Synthesis of Biaryl Diphosphines via a Stepwise Regioselective Double
 Diels&#x2212;Alder Cycloaddition&#x2212;Elimination Sequence: Efficient
 Ligands for the Palladium-Catalyzed Amination of Aromatic Bromides
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              5273
_journal_paper_doi               10.1021/om9004862
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C38 H32 P2 O4, C H2 Cl2'
_chemical_formula_sum            'C42 H34 Cl2 O4 P2'
_chemical_formula_weight         735.53
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 97.566(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.6012(8)
_cell_length_b                   13.4646(4)
_cell_length_c                   20.9644(6)
_cell_measurement_reflns_used    4439
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.16
_cell_measurement_theta_min      2.93
_cell_volume                     6883.9(4)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type
'Oxford Diffraction Gemini A Ultra diffractometer'
_diffrn_measurement_method       'thin-slice \w scans'
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'sealed tube with Enhance optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_sigmaI/netI    0.1252
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20571
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.98
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrysAlisPro
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3056
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5823
_refine_ls_number_restraints     299
_refine_ls_restrained_S_all      0.815
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                3154
_reflns_number_total             5823
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            om9004862_si_002.cif
_cod_data_source_block           sd258_compound4
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4069892