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_4034075
_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            'C23 H28 N4 O4'
_chemical_formula_weight         424.49
_chemical_melting_point          482
_chemical_name_systematic
N-(1-(tert-Butylcarbamoyl)-3-(4-nitrophenyl)-cyclohexyl)-picolinamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.124(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.286(3)
_cell_length_b                   16.253(6)
_cell_length_c                   13.955(5)
_cell_measurement_reflns_used    6213
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      4.22
_cell_volume                     2296.6(14)
_computing_cell_refinement       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_collection       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2014)'
_computing_molecular_graphics
; 
Ortep-3 Ver 2.02 L.J. Farrugia (1997) J. Appl. Cryst. 30, 565 
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Bruker, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 52.0833
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker D8 Venture \k-geometry diffractometer 208039-01'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15369
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.183
_diffrn_reflns_theta_min         4.213
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6283
_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    1.228
_exptl_crystal_description       Prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4180
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1447
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.6768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2048
_reflns_number_total             4180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01436_si_003.cif
_cod_data_source_block           165PGL18
_cod_original_cell_volume        2296.7(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034075
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.773
_shelx_estimated_absorpt_t_max   0.971
_exptl_absorpt_special_details
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 1.54179   10.278   16.225   13.925   89.992  100.240   89.970
;
_shelx_res_checksum              38385
_shelx_hkl_checksum              77803