Regioselective Hydronickelation of Allenes and Its Application to the Hydrocyanative Carbocyclization Reaction of Allene-Ynes and Bis-Allenes
Yuka Amako; Hiroto Hori; Shigeru Arai; Atsushi Nishida; Journal of Organic Chemistry 78 (2013) 10763–10775; doi:10.1021/jo401758v

data_4028715
_publ_section_title
;
 Regioselective Hydronickelation of Allenes and Its Application to the
 Hydrocyanative Carbocyclization Reaction of Allene-Ynes and Bis-Allenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10763
_journal_page_last               10775
_journal_paper_doi               10.1021/jo401758v
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C17 H20 N2 O2 S'
_chemical_formula_weight         316.41
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.56651(13)
_cell_length_b                   11.1912(3)
_cell_length_c                   22.4202(5)
_cell_measurement_temperature    93(2)
_cell_volume                     1647.60(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17633
_diffrn_reflns_theta_full        68.18
_diffrn_reflns_theta_max         68.18
_diffrn_reflns_theta_min         3.94
_exptl_absorpt_coefficient_mu    1.812
_exptl_absorpt_correction_T_max  0.9148
_exptl_absorpt_correction_T_min  0.8395
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.44(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0712P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1365
_reflns_number_gt                2623
_reflns_number_total             3001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401758v_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1647.60(6)
_cod_database_code               4028715