C-H Activation in Primary 3-Phenylpropylamines: Synthesis of Seven-Membered Palladacycles through Orthometalation. Stoichiometric Preparation of Benzazepinones and Catalytic Synthesis of Ureas.
Frutos-Pedreño, Roberto; García-Sánchez, Eva; Oliva-Madrid, María José; Bautista, Delia; Martínez-Viviente, Eloísa; Saura-Llamas, Isabel; Vicente, José; Inorganic chemistry 55 (2016) 5520–5533; doi:10.1021/acs.inorgchem.6b00542

data_4347737
_publ_section_title
;
 C-H Activation in Primary 3-Phenylpropylamines: Synthesis of
 Seven-Membered Palladacycles through Orthometalation. Stoichiometric
 Preparation of Benzazepinones and Catalytic Synthesis of Ureas.
;
_journal_issue                   11
_journal_name_full               'Inorganic chemistry'
_journal_page_first              5520
_journal_page_last               5533
_journal_paper_doi               10.1021/acs.inorgchem.6b00542
_journal_volume                  55
_journal_year                    2016
_chemical_formula_sum            'C29 H32 Cl N O0.5 P Pd'
_chemical_formula_weight         575.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 118.6591(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.6928(11)
_cell_length_b                   10.1025(5)
_cell_length_c                   23.9981(11)
_cell_measurement_reflns_used    9242
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.60
_cell_measurement_theta_min      2.23
_cell_volume                     5253.1(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2011)'
_computing_data_collection       'APEX2 2014.1-1 (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            162489
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.614
_diffrn_reflns_theta_min         1.934
_diffrn_source                   'high brilliance microfocus sealed tube '
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.8115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       block
_exptl_crystal_F_000             2360
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.568
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         8068
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0221P)^2^+10.6698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0568
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6923
_reflns_number_total             8068
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic6b00542_si_001.cif
_cod_data_source_block           rfj29a_0msp
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C29 H32 Cl N O0.50 P Pd'
_cod_database_code               4347737
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.835
_shelx_estimated_absorpt_t_max   0.924
_shelx_res_checksum              95272
_shelx_hkl_checksum              63746