Indium- and zinc-catalyzed enantioselective amide propargylation of aldehydes with stannylated allenyl amides.
Sengoku, Tetsuya; Ikeda, Ikuhei; Ai, Keisuke; Takahashi, Masaki; Yoda, Hidemi; Organic & biomolecular chemistry 17 (2019) 2614–2618; doi:10.1039/c9ob00040b

data_7156677
_publ_section_title
;
 Indium- and zinc-catalyzed enantioselective amide propargylation of
 aldehydes with stannylated allenyl amides.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2614
_journal_page_last               2618
_journal_paper_doi               10.1039/c9ob00040b
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C17 H16 Cl N O4'
_chemical_formula_sum            'C17 H16 Cl N O4'
_chemical_formula_weight         333.77
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-11-13 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.7177(5)
_cell_length_b                   7.7029(6)
_cell_length_c                   35.315(3)
_cell_measurement_reflns_used    3784
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.50
_cell_volume                     1555.4(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b30'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b30 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b30'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            14382
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.307
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696.00
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.27
_refine_ls_abs_structure_details
;
 Flack x determined using 1181 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3534
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0734P)^2^+0.0480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3262
_reflns_number_total             3534
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9ob00040b2.cif
_cod_data_source_block           sengoku-p-Cl-ph-181021a
_cod_depositor_comments          'Adding full bibliography for 7156677.cif.'
_cod_database_code               7156677
_shelx_res_checksum              61553