Synthesis of a Chiral C2-Symmetric Sterically Hindered Pyrrolidine Nitroxide Radical via Combined Iterative Nucleophilic Additions and Intramolecular 1,3-Dipolar Cycloadditions to Cyclic Nitrones
Denis A. Morozov; Igor A. Kirilyuk; Denis A. Komarov; Andrea Goti; Irina Yu. Bagryanskaya; Natalia V. Kuratieva; Igor A. Grigor'ev; Journal of Organic Chemistry 77 (2012) 10688–10698; doi:10.1021/jo3019158

data_4027758
_publ_contact_author_address
;Institute of Organic Chemistry,
SB Russian Academy of Sciences,
Akad. Lavrentiev prospekt 9,
Novosibirsk 90,
630090 Russia
;
_publ_contact_author_email       m_falcon@nioch.nsc.ru
_publ_contact_author_fax         7(383)3309752
_publ_contact_author_name        'Denis A. Morozov'
_publ_contact_author_phone       7(383)3307387
_publ_section_title
;
 Synthesis of a Chiral C2-Symmetric Sterically Hindered Pyrrolidine
 Nitroxide Radical via Combined Iterative Nucleophilic Additions and
 Intramolecular 1,3-Dipolar Cycloadditions to Cyclic Nitrones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10688
_journal_page_last               10698
_journal_paper_doi               10.1021/jo3019158
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H40 N O5'
_chemical_formula_sum            'C22 H40 N O5'
_chemical_formula_weight         398.55
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.886(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3054(4)
_cell_length_b                   10.0632(4)
_cell_length_c                   10.8269(3)
_cell_measurement_reflns_used    5989
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.53
_cell_measurement_theta_min      2.77
_cell_volume                     1118.73(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 25
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       '\f 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  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7858
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.98
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       plate
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4307
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0833P)^2^+0.0870P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                4143
_reflns_number_total             4307
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo3019158_si_001.cif
_cod_data_source_block           mor001
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4027758