Pd-Mediated γ-C(sp<sup>3</sup>)-H Bond Activation in Ammonia-Ugi 4-CR Adducts by Using Picolinamide as Directing Group.
Alemán-Ponce de León, Diego; Sánchez-Chávez, Anahí C; Polindara-García, Luis A; The Journal of organic chemistry 84 (2019) 12809–12834; doi:10.1021/acs.joc.9b01436

data_4034076
_publ_section_title
;
 Pd-Mediated \g-C(sp<sup>3</sup>)-H Bond Activation in Ammonia-Ugi 4-CR
 Adducts by Using Picolinamide as Directing Group.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12809
_journal_page_last               12834
_journal_paper_doi               10.1021/acs.joc.9b01436
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C27 H36 N4 O4'
_chemical_formula_weight         480.60
_chemical_melting_point          420
_chemical_name_systematic
'tert-Butyl 3-(tert-butylcarbamoyl)-5-phenyl-3-(picolinamido)piperidine-1-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                93.9630(10)
_cell_angle_beta                 101.7010(10)
_cell_angle_gamma                111.3250(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2453(2)
_cell_length_b                   12.0977(2)
_cell_length_c                   13.4707(2)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.39
_cell_volume                     1357.37(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18288
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.291
_diffrn_reflns_theta_min         3.392
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       Prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.383
_exptl_crystal_size_min          0.224
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+0.2469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4444
_reflns_number_total             4951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01436_si_004.cif
_cod_data_source_block           419PGL18_a
_cod_database_code               4034076
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.761
_shelx_estimated_absorpt_t_max   0.869
_shelx_res_checksum              6152
_shelx_hkl_checksum              79800