Is the A-Ring of Sparteine Essential for High Enantioselectivity in the Asymmetric Lithiation-Substitution of N-Boc-pyrrolidine?
Puay-Wah Phuan; James C. Ianni; Marisa C. Kozlowski; Journal of the American Chemical Society 126 (2004) 15473–15479; doi:10.1021/ja046321i

data_4113224
_publ_section_title
;
 Is the A-Ring of Sparteine Essential for High Enantioselectivity in the
 Asymmetric Lithiation-Substitution of N-Boc-pyrrolidine?
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15473
_journal_page_last               15479
_journal_paper_doi               10.1021/ja046321i
_journal_volume                  126
_journal_year                    2004
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H23 I N2'
_chemical_formula_weight         310.21
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.7710(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6236(13)
_cell_length_b                   10.7904(11)
_cell_length_c                   11.9528(14)
_cell_measurement_temperature    143(1)
_cell_volume                     1369.5(3)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8814
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    2.310
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6777
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         5143
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0740
_reflns_number_gt                4840
_reflns_number_total             5143
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja046321isi20040622_104610.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4113224