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_4069894
_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         'C33 H28 O2 P, 0.5 H2 O'
_chemical_formula_sum            'C33 H29 O2.5 P2'
_chemical_formula_weight         527.50
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.362(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.010(2)
_cell_length_b                   16.589(6)
_cell_length_c                   15.323(5)
_cell_measurement_reflns_used    96
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.50
_cell_volume                     2743.8(14)
_computing_cell_refinement       EvalCCD
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        EvalCCD
_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_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26311
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0332P)^2^+1.7890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                4689
_reflns_number_total             6158
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            om9004862_si_002.cif
_cod_data_source_block           sd247_compound12
_cod_original_cell_volume        2743.9(15)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C33 H29 O2.50 P2'
_cod_database_code               4069894