Eight-Membered Palladacycles Derived from the Insertion of Olefins into the Pd−C Bond of Ortho-Palladated Pharmaceuticals Phenethylamine and Phentermine. Synthesis of Stable Heck-Type Intermediates Containing Accessible β-Hydrogens and Its Use in the Synthesis of 2-Styrylphenethylamines, Tetrahydroisoquinolines, and Eight-Membered Cyclic Amidines†
Vicente, José; Saura-Llamas, Isabel; García-López, José-Antonio; Bautista, Delia; Organometallics 29 (2010) 4320–; doi:10.1021/om100738z

data_4066963
_publ_section_title
;
 Eight-Membered Palladacycles Derived from the Insertion of Olefins into
 the Pd&#x2212;C Bond of Ortho-Palladated Pharmaceuticals Phenethylamine
 and Phentermine. Synthesis of Stable Heck-Type Intermediates Containing
 Accessible \b-Hydrogens and Its Use in the Synthesis of
 2-Styrylphenethylamines, Tetrahydroisoquinolines, and Eight-Membered
 Cyclic Amidines&#x2020;
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              4320
_journal_paper_doi               10.1021/om100738z
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C20 H27 Cl N2 O Pd'
_chemical_formula_weight         453.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 90.535(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2796(4)
_cell_length_b                   17.1677(8)
_cell_length_c                   27.9086(13)
_cell_measurement_reflns_used    5332
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      2.37
_cell_volume                     3966.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       \w-scan
_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  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            45462
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    1.080
_exptl_absorpt_correction_T_max  0.9380
_exptl_absorpt_correction_T_min  0.8049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       neddle
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    'NH2 free, methyls rigid others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         9177
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0318P)^2^+3.5114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                8130
_reflns_number_total             9177
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100738z_si_002.cif
_cod_data_source_block           jae901s
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               4066963