Insertion of Allenes into the Pd–C Bond of Ortho-Palladated Primary Arylamines of Biological Relevance: Phenethylamine, Phentermine, (l)-Phenylalanine Methyl Ester, and (l)-Tryptophan Methyl Ester. Synthesis of Tetrahydro-3-benzazepines and Their Salts
García-López, José-Antonio; Saura-Llamas, Isabel; McGrady, John E.; Bautista, Delia; Vicente, José; Organometallics 31 (2012) 8333–; doi:10.1021/om300928j

data_4079674
_publ_section_title
;
 Insertion of Allenes into the Pd--C Bond of Ortho-Palladated Primary
 Arylamines of Biological Relevance: Phenethylamine, Phentermine,
 (l)-Phenylalanine Methyl Ester, and (l)-Tryptophan Methyl Ester.
 Synthesis of Tetrahydro-3-benzazepines and Their Salts
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              8333
_journal_paper_doi               10.1021/om300928j
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C13 H18 Br N'
_chemical_formula_weight         268.19
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 107.163(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1828(7)
_cell_length_b                   7.6142(4)
_cell_length_c                   13.2748(7)
_cell_measurement_reflns_used    5031
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      2.59
_cell_volume                     1273.14(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHEXTL'
_computing_publication_material  'Bruker SHEXTL'
_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 0.999
_diffrn_measured_fraction_theta_max 0.943
_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  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14705
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.18
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    3.198
_exptl_absorpt_correction_T_max  0.8071
_exptl_absorpt_correction_T_min  0.4902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment
'NH2 free with SADI, methyls rigid, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         5709
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0201
_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^)+(0.0299P)^2^+0.0501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0493
_reflns_number_gt                5547
_reflns_number_total             5709
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300928j_si_002.cif
_cod_data_source_block           jae545s
_cod_original_sg_symbol_H-M      'P 2(1)'
_cod_database_code               4079674