Palladium-Catalyzed Intramolecular Hydroaminocarbonylation to Lactams: Additive-Free Protocol Initiated by Palladium Hydride
Hu, Yue; Shen, Zhiqiang; Huang, Hanmin; ACS Catalysis 6 (2016) 6785–; doi:10.1021/acscatal.6b01939

data_4513953
_publ_section_title
;
 Palladium-Catalyzed Intramolecular Hydroaminocarbonylation to Lactams:
 Additive-Free Protocol Initiated by Palladium Hydride
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              6785
_journal_paper_doi               10.1021/acscatal.6b01939
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C24 H55 Cl P2 Pd'
_chemical_formula_sum            'C24 H55 Cl P2 Pd'
_chemical_formula_weight         547.47
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.2740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   45.941(3)
_cell_length_b                   8.7162(6)
_cell_length_c                   14.6019(10)
_cell_measurement_reflns_used    6233
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.01
_cell_measurement_theta_min      2.81
_cell_volume                     5713.4(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15421
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         0.907
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  0.8462
_exptl_absorpt_correction_T_min  0.8130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.826
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5612
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0357P)^2^+5.9741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0819
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4141
_reflns_number_total             5612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b01939_si_002.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 4513953--4513955.cif.'
_cod_original_cell_volume        5713.5(7)
_cod_database_code               4513953
_shelx_estimated_absorpt_t_max   0.846
_shelx_estimated_absorpt_t_min   0.813
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H3'C-H10A
 2.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C8') \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(C6') \\sim Ueq, Uanis(C7') \\sim Ueq: with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(C2) \\sim Ueq, Uanis(C2') \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C3')
\\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C4') \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C2(0.7) H2A(0.7) H2B(0.7) H2C(0.7) C3(0.7) H3A(0.7) H3B(0.7)
 H3C(0.7) C4(0.7) H4A(0.7) H4B(0.7) H4C(0.7) C6(0.4) H6A(0.4) H6B(0.4) H6C(0.4)
 C7(0.4) H7A(0.4) H7B(0.4) H7C(0.4) C8(0.4) H8A(0.4) H8B(0.4) H8C(0.4) C2'(0.3)
 H2'A(0.3) H2'B(0.3) H2'C(0.3) C3'(0.3) H3'A(0.3) H3'B(0.3) H3'C(0.3) C4'(0.3)
 H4'A(0.3) H4'B(0.3) H4'C(0.3) C6'(0.6) H6'A(0.6) H6'B(0.6) H6'C(0.6) C7'(0.6)
 H7'A(0.6) H7'B(0.6) H7'C(0.6) C8'(0.6) H8'A(0.6) H8'B(0.6) H8'C(0.6)
5.a Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,
 H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C),
 C24(H24A,H24B,H24C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C6(H6A,
 H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C2'(H2'A,H2'B,H2'C), C3'(H3'A,H3'B,
 H3'C), C4'(H4'A,H4'B,H4'C), C6'(H6'A,H6'B,H6'C), C7'(H7'A,H7'B,H7'C), C8'(H8'A,
 H8'B,H8'C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'