Diastereoselective [3 + 2] vs [4 + 2] Cycloadditions of Nitroprolinates with α,β-Unsaturated Aldehydes and Electrophilic Alkenes: An Example of Total Periselectivity.
Selva, Verónica; Larrañaga, Olatz; Castelló, Luis M; Nájera, Carmen; Sansano, José M; de Cózar, Abel; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b00903

data_4032565
_publ_section_title
;
 Diastereoselective [3 + 2] vs [4 + 2] Cycloadditions of Nitroprolinates
 with \a,\b-Unsaturated Aldehydes and Electrophilic Alkenes: An Example of
 Total Periselectivity.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00903
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C32 H29 N3 O6'
_chemical_formula_sum            'C32 H29 N3 O6'
_chemical_formula_weight         551.58
_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
_audit_update_record
;
2016-05-24 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.976(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.649(2)
_cell_length_b                   11.121(3)
_cell_length_c                   14.546(4)
_cell_measurement_reflns_used    629
_cell_measurement_temperature    298(1)
_cell_measurement_theta_max      20.85
_cell_measurement_theta_min      2.3
_cell_volume                     1393.8(6)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1235
_diffrn_reflns_av_sigmaI/netI    0.1911
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11900
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.5813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4907
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.2005
_refine_ls_R_factor_gt           0.0662
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0180P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                1973
_reflns_number_total             4907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00903_si_002.cif
_cod_data_source_block           a305
_cod_original_cell_volume        1393.8(7)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4032565