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_1508770
_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            'C22 H22 F6 N2'
_chemical_formula_weight         428.42
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 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                 107.769(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5477(6)
_cell_length_b                   9.8838(3)
_cell_length_c                   14.5179(7)
_cell_measurement_reflns_used    2405
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     1987.89(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.044
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15226
_diffrn_reflns_theta_full        66.71
_diffrn_reflns_theta_max         66.71
_diffrn_reflns_theta_min         4.47
_exptl_absorpt_coefficient_mu    1.072
_exptl_absorpt_correction_T_max  0.9288
_exptl_absorpt_correction_T_min  0.7393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0752P)^2^+1.1189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1560
_reflns_number_gt                2932
_reflns_number_total             3438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302855z_si_001.cif
_cod_data_source_block           stu6628
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               1508770