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_7120168
_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         'C22 H28 N O4 S'
_chemical_formula_sum            'C22 H28 N O4 S'
_chemical_formula_weight         402.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                104.226(7)
_cell_angle_beta                 99.435(7)
_cell_angle_gamma                96.838(7)
_cell_formula_units_Z            2
_cell_length_a                   9.3258(3)
_cell_length_b                   9.3714(3)
_cell_length_c                   12.7379(3)
_cell_measurement_reflns_used    10779
_cell_measurement_temperature    133
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.65
_cell_volume                     1049.62(7)
_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 0.979
_diffrn_measured_fraction_theta_max 0.977
_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  0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11646
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         3.654
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.593
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             430.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.5157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3267
_reflns_number_total             3755
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c7cc03127k2.cif
_cod_data_source_block           iman-1
_cod_database_code               7120168
_shelx_res_checksum              38654