Diastereoselectivity of polar and radical couplings in electrophilic substitutions of rigid 2-lithio-N-methylpyrrolidines.
Gawley, Robert E.; Eddings, Daniel B.; Santiago, Marcelina; Vicic, Davic A.; Organic & biomolecular chemistry 4 (2006) 4285–4291; doi:10.1039/b608013h

data_7151295
_publ_section_title
;
 Diastereoselectivity of polar and radical couplings in electrophilic
 substitutions of rigid 2-lithio-N-methylpyrrolidines.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4285
_journal_page_last               4291
_journal_paper_doi               10.1039/b608013h
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C11 H22 I N O '
_chemical_formula_sum            'C11 H22 I N O'
_chemical_formula_weight         311.21
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.1485(11)
_cell_length_b                   13.160(2)
_cell_length_c                   14.239(2)
_cell_measurement_reflns_used    3141
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      34.6
_cell_measurement_theta_min      2.1
_cell_volume                     1339.5(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SHELXS97
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18861
_diffrn_reflns_theta_full        34.58
_diffrn_reflns_theta_max         34.58
_exptl_absorpt_coefficient_mu    2.367
_exptl_absorpt_correction_T_max  0.492
_exptl_absorpt_correction_T_min  0.340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624.00
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.51
_refine_diff_density_min         -1.30
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.25(5)
_refine_ls_extinction_coef       20(6)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.762
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     151
_refine_ls_number_reflns         3087
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/\s^2^(Fo^2^)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                2593
_reflns_number_total             3087
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            b608013h.txt
_cod_data_source_block           CO2_New_1b
_cod_original_cell_volume        1339.5(4)
_cod_original_formula_sum        'C11 H22 I N O '
_cod_database_code               7151295