Organocatalytic Enantioselective Amination of 2-Substituted Indolin-3-ones: A Strategy for the Synthesis of Chiral α-Hydrazino Esters.
Yarlagadda, Suresh; Ramesh, B.; Ravikumar Reddy, C.; Srinivas, L.; Sridhar, B.; Subba Reddy, B. V.; Organic letters 19 (2017) 170–173; doi:10.1021/acs.orglett.6b03473

data_1544944
_publ_section_title
;
 Organocatalytic Enantioselective Amination of 2-Substituted
 Indolin-3-ones: A Strategy for the Synthesis of Chiral \a-Hydrazino
 Esters.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              170
_journal_page_last               173
_journal_paper_doi               10.1021/acs.orglett.6b03473
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C26 H31 N3 O7'
_chemical_formula_sum            'C26 H31 N3 O7'
_chemical_formula_weight         497.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4235(8)
_cell_length_b                   17.6443(17)
_cell_length_c                   17.7369(17)
_cell_measurement_reflns_used    8138
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.30
_cell_volume                     2636.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         2.309
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker,2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2418 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.1449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                5899
_reflns_number_total             6365
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03473_si_002.cif
_cod_data_source_block           BC64m
_cod_depositor_comments          'Adding full bibliography for 1544944.cif.'
_cod_database_code               1544944
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              53078
_shelx_hkl_checksum              19288