Highly diastereoselective synthesis of 3-indolylglycines via an asymmetric oxidative heterocoupling reaction of a chiral nickel(II) complex and indoles
Daizong Lin; Jiang Wang; Xu Zhang; Shengbin Zhou; Jie Lian; Hualiang Jiang; Hong Liu; Chem.Commun. 49 (2013) 2575–; doi:10.1039/c3cc38908a

data_7108986
_publ_section_title
;
 Highly diastereoselective synthesis of 3-indolylglycines via an
 asymmetric oxidative heterocoupling reaction of a chiral nickel(II)
 complex and indoles
;
_journal_name_full               Chem.Commun.
_journal_page_first              2575
_journal_paper_doi               10.1039/c3cc38908a
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C35 H30 N4 Ni O3'
_chemical_formula_weight         613.34
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 99.011(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.435(5)
_cell_length_b                   9.023(4)
_cell_length_c                   15.152(7)
_cell_measurement_reflns_used    565
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.130
_cell_measurement_theta_min      4.847
_cell_volume                     1544.1(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_sigmaI/netI    0.2166
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8310
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0978
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         5203
_refine_ls_number_restraints     319
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1828
_refine_ls_R_factor_gt           0.1047
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1989
_reflns_number_gt                2681
_reflns_number_total             5203
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc38908a.txt
_cod_data_source_block           cd212238
_cod_original_cell_volume        1544.2(13)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7108986