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_4069893
_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         'C37 H30 Cl2 O P2 Pd, 2 C H2 Cl2'
_chemical_formula_sum            'C39 H34 Cl6 O P2 Pd'
_chemical_formula_weight         899.70
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.92(3)
_cell_angle_beta                 93.40(3)
_cell_angle_gamma                103.874(16)
_cell_formula_units_Z            2
_cell_length_a                   11.238(3)
_cell_length_b                   11.472(3)
_cell_length_c                   14.926(3)
_cell_measurement_reflns_used    285
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     1860.6(8)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43806
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.94
_exptl_absorpt_coefficient_mu    1.048
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         8517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0272
_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^)+(0.0313P)^2^+2.2173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                7380
_reflns_number_total             8517
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            om9004862_si_002.cif
_cod_data_source_block           sd280_compound7
_cod_original_cell_volume        1860.7(7)
_cod_database_code               4069893