Asymmetric synthesis of alpha-(1-oxoisoindolin-3-yl)glycine: synthetic and mechanistic challenges
Tingting Li; Shengbin Zhou; Jiang Wang; Jose Luis Acena; Vadim A. Soloshonok; Hong Liu; Chem.Commun. 51 (2015) 1624–; doi:10.1039/C4cc05659K

data_7116410
_publ_section_title
;
 Asymmetric synthesis of alpha-(1-oxoisoindolin-3-yl)glycine: synthetic
 and mechanistic challenges
;
_journal_name_full               Chem.Commun.
_journal_page_first              1624
_journal_paper_doi               10.1039/C4cc05659K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C37 H38 N4 Ni O6'
_chemical_formula_weight         693.42
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-07-21 deposited with the CCDC.
2014-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.4940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2226(5)
_cell_length_b                   39.325(2)
_cell_length_c                   10.4346(7)
_cell_measurement_reflns_used    6808
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.648
_cell_measurement_theta_min      4.420
_cell_volume                     3372.9(4)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20431
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         1.952
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6858
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
; 
 Flack x determined using 4958 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.033(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     881
_refine_ls_number_reflns         12934
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.1850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                11757
_reflns_number_total             12934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc05659k2.cif
_cod_data_source_block           cd214120
_cod_original_cell_volume        3373.0(4)
_cod_database_code               7116410
_shelxl_version_number           2013-4
_shelx_res_checksum              85787