Efficient Synthesis of Chiral 2,2'-Bipyrrolidines by an anti-Selective Alkene Diamination.
Müller, Christian H; Fröhlich, Roland; Daniliuc, Constantin G.; Hennecke, Ulrich; Organic letters 14 (2012) 5944–5947; doi:10.1021/ol302855z

data_1508772
_publ_section_title
;
 Efficient Synthesis of Chiral 2,2'-Bipyrrolidines by an anti-Selective
 Alkene Diamination.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5944
_journal_page_last               5947
_journal_paper_doi               10.1021/ol302855z
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C20 H22 N4 O4'
_chemical_formula_weight         382.42
_space_group_IT_number           142
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4bd 2c'
_symmetry_space_group_name_H-M   'I 41/a c d :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   17.6875(4)
_cell_length_b                   17.6875(4)
_cell_length_c                   26.5075(7)
_cell_measurement_reflns_used    3573
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      4.08
_cell_volume                     8292.8(3)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11145
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         4.22
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3232
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0693
_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^)+(0.0972P)^2^+9.9659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1905
_refine_ls_wR_factor_ref         0.2111
_reflns_number_gt                1244
_reflns_number_total             1816
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302855z_si_001.cif
_cod_data_source_block           STU6532
_cod_original_sg_symbol_H-M      I4(1)/acd
_cod_database_code               1508772