Organocatalytic synthesis of enantiopure spiro acenaphthyl-pyrrolizidine/pyrrolidines: justifying the regioselectivity based on a distortion/interaction model.
Shahrestani, Naeimeh; Khosravi, Hormoz; Jadidi, Khosrow; Notash, Behrouz; Naderi, Soheila; Organic & biomolecular chemistry 17 (2019) 7013–7024; doi:10.1039/c9ob01197h

data_7156974
_publ_section_title
;
 Organocatalytic synthesis of enantiopure spiro
 acenaphthyl-pyrrolizidine/pyrrolidines: justifying the regioselectivity
 based on a distortion/interaction model.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7013
_journal_page_last               7024
_journal_paper_doi               10.1039/c9ob01197h
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C28 H26 N2 O4'
_chemical_formula_sum            'C28 H26 N2 O4'
_chemical_formula_weight         454.51
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-01-09 deposited with the CCDC.    2019-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1876(16)
_cell_length_b                   14.121(3)
_cell_length_c                   19.915(4)
_cell_measurement_reflns_used    6053
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.15
_cell_measurement_theta_min      2.50
_cell_volume                     2302.5(8)
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_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  0.1004
_diffrn_reflns_av_sigmaI/netI    0.1469
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10660
_diffrn_reflns_theta_full        29.15
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         2.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1373
_refine_ls_R_factor_gt           0.0795
_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^)+(0.0438P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                3714
_reflns_number_total             6053
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob01197h2.cif
_cod_data_source_block           khc580h
_cod_depositor_comments
'Adding full bibliography for 7156973--7156975.cif.'
_cod_database_code               7156974