Nickel-Catalyzed Hydrocarboxylation of Ynamides with CO2 and H2O: Observation of Unexpected Regioselectivity
Doi, Ryohei; Abdullah, Iman; Taniguchi, Takahisa; Saito, Nozomi; Sato, Yoshihiro; Chem. Commun.  (2017) –; doi:10.1039/C7CC03127K

data_7120169
_publ_section_title
;
 Nickel-Catalyzed Hydrocarboxylation of Ynamides with CO2 and H2O:
 Observation of Unexpected Regioselectivity
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03127K
_journal_year                    2017
_chemical_formula_moiety         'C24 H25 N3 Ni O4 S'
_chemical_formula_sum            'C24 H25 N3 Ni O4 S'
_chemical_formula_weight         510.24
_chemical_properties_physical    ', Air-sensitive'
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2017-04-23 deposited with the CCDC.
2017-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.723(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   18.6357(6)
_cell_length_b                   6.4232(2)
_cell_length_c                   19.8474(7)
_cell_measurement_reflns_used    18992
_cell_measurement_temperature    133
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      4.04
_cell_volume                     2222.04(17)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/8 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      133
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22588
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.218
_diffrn_reflns_theta_min         4.047
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.455
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064.00
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4072
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0647P)^2^+1.9822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3257
_reflns_number_total             4072
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c7cc03127k2.cif
_cod_data_source_block           01rd127
_cod_original_cell_volume        2222.05(17)
_cod_database_code               7120169
_shelx_res_checksum              38277