Highly enantioselective synthesis of chiral 7-ring O- and N-heterocycles by a one-pot nitro-Michael-cyclization tandem reaction
Renate Rohlmann; Constantin-Gabriel Daniliuc; Olga Garcia Mancheno; Chem.Commun. 49 (2013) 11665–; doi:10.1039/c3cc47397j

data_7110121
_publ_section_title
;
 Highly enantioselective synthesis of chiral 7-ring O- and N-heterocycles
 by a one-pot nitro-Michael-cyclization tandem reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              11665
_journal_paper_doi               10.1039/c3cc47397j
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.31
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_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                 95.960(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2054(1)
_cell_length_b                   10.5740(1)
_cell_length_c                   8.6556(1)
_cell_measurement_reflns_used    1080
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     746.934(14)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3697
_diffrn_reflns_theta_full        67.01
_diffrn_reflns_theta_max         67.01
_diffrn_reflns_theta_min         7.86
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  0.9298
_exptl_absorpt_correction_T_min  0.8021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.096
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0410P)^2^+0.1097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0786
_reflns_number_gt                2077
_reflns_number_total             2081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc47397j.txt
_cod_data_source_block           gar6954
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7110121