Syn-selective Kobayashi aldol reaction using the E,E-vinylketene silyl N,O-acetal.
Mukaeda, Yuki; Kato, Takuya; Hosokawa, Seijiro; Organic letters 14 (2012) 5298–5301; doi:10.1021/ol3024677

data_1508692
_publ_section_title
;
 Syn-selective Kobayashi aldol reaction using the E,E-vinylketene silyl
 N,O-acetal.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5298
_journal_page_last               5301
_journal_paper_doi               10.1021/ol3024677
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H24 Br N O4'
_chemical_formula_sum            'C19 H24 Br N O4'
_chemical_formula_weight         410.31
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.781(5)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   25.422(5)
_cell_length_b                   6.1383(13)
_cell_length_c                   12.182(3)
_cell_measurement_reflns_used    7402
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.25
_cell_volume                     1878.7(7)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9232
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.217
_exptl_absorpt_correction_T_max  0.412
_exptl_absorpt_correction_T_min  0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848.00
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_refine_diff_density_max         1.550
_refine_diff_density_min         -0.720
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1904 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.017(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4242
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1677
_reflns_number_gt                3487
_reflns_number_total             4242
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol3024677_si_002.cif
_cod_data_source_block           4-bromobenzaldehyde
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'AD' changed to 'ad'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1878.6(7)
_cod_database_code               1508692