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_4034074
_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            'C17 H25 N3 O2'
_chemical_formula_weight         303.40
_chemical_melting_point_gt       433
_chemical_name_systematic
N-(1-(tert-Butylcarbamoyl)cyclohexyl)picolinamide
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   10.6027(2)
_cell_length_b                   10.6027(2)
_cell_length_c                   26.4100(5)
_cell_measurement_reflns_used    9045
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      68.08
_cell_measurement_theta_min      5.10
_cell_volume                     2571.18(8)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1279
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            30983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.071
_diffrn_reflns_theta_min         4.816
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  0.9178
_exptl_absorpt_correction_T_min  0.8514
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL (Sheldrick, 2014/7)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       Prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.196
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1308 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0540P)^2^+0.2663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2950
_reflns_number_total             3129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01436_si_002.cif
_cod_data_source_block           301PGL18_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_chemical_melting_point' was changed to
'_chemical_melting_point_gt' since the value was specified as 'more
than' ('>') a certain temperature.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2571.18(11)
_cod_database_code               4034074
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.798
_shelx_estimated_absorpt_t_max   0.888
_shelx_res_checksum              8282
_shelx_hkl_checksum              86970