Organocatalytic Asymmetric Domino Michael/Acyl Transfer Reaction between γ/δ-Hydroxyenones and α-Nitroketones.
Mondal, Keshab; Pan, Subhas Chandra; The Journal of organic chemistry 83 (2018) 5301–5312; doi:10.1021/acs.joc.8b00436

data_4035532
_publ_section_title
;
 Organocatalytic Asymmetric Domino Michael/Acyl Transfer Reaction between
 \g/\d-Hydroxyenones and \a-Nitroketones.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5301
_journal_page_last               5312
_journal_paper_doi               10.1021/acs.joc.8b00436
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration S
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C18 H16 Br N O5'
_chemical_formula_sum            'C18 H16 Br N O5'
_chemical_formula_weight         406.22
_chemical_name_systematic        Unknown
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.715(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.8540(5)
_cell_length_b                   5.5969(3)
_cell_length_c                   15.0011(9)
_cell_measurement_reflns_used    3612
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      3.76
_cell_volume                     868.09(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3255
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.76
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.396
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Neddle
_exptl_crystal_F_000             412
_exptl_crystal_recrystallization_method
'Hexane and dichloromethane solvent mixture'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.020(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2573
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.0828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                2023
_reflns_number_total             2573
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00436_si_002.cif
_cod_data_source_block           km-p6-4-br-147
_cod_original_cell_volume        868.09(8)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035532