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_4034779
_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         'C13 H16 N2 O2'
_chemical_formula_sum            'C13 H16 N2 O2'
_chemical_formula_weight         232.28
_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                   7.2780(2)
_cell_length_b                   17.8268(5)
_cell_length_c                   18.0726(5)
_cell_measurement_reflns_used    17079
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.48
_cell_volume                     2344.80(11)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26132
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.223
_diffrn_reflns_theta_min         3.483
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.27
_refine_ls_abs_structure_details
;
 Flack x determined using 1116 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0839P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1601
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3374
_reflns_number_total             4274
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo8b00743_si_002.cif
_cod_data_source_block           180227takeuchi
_cod_original_cell_volume        2344.80(12)
_cod_database_code               4034779
_shelx_res_checksum              84984
_shelx_hkl_checksum              97098