Direct Catalytic Asymmetric Aldol Reaction of α-Vinyl Acetamide.
Takeuchi, Toshifumi; Kumagai, Naoya; Shibasaki, Masakatsu; The Journal of organic chemistry 83 (2018) 5851–5858; doi:10.1021/acs.joc.8b00743

data_4034778
_publ_section_title
;
 Direct Catalytic Asymmetric Aldol Reaction of \a-Vinyl Acetamide.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5851
_journal_page_last               5858
_journal_paper_doi               10.1021/acs.joc.8b00743
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C26 H41 N2 O2 Si'
_chemical_formula_sum            'C26 H41 N2 O2 Si'
_chemical_formula_weight         441.71
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   7.6510(7)
_cell_length_b                   18.5007(15)
_cell_length_c                   38.062(3)
_cell_measurement_reflns_used    11886
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.09
_cell_measurement_theta_min      3.33
_cell_volume                     5387.6(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_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      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0951
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            48061
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.332
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.934
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1928.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details
;
 Flack x determined using 1456 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     595
_refine_ls_number_reflns         9783
_refine_ls_number_restraints     111
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0716P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1621
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                5407
_reflns_number_total             9783
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo8b00743_si_003.cif
_cod_data_source_block           180320takeuchi
_cod_database_code               4034778
_shelx_res_checksum              1755
_shelx_hkl_checksum              63360