Ring opening/C-N cyclization of activated aziridines with carbon nucleophiles: highly diastereo- and enantioselective synthesis of tetrahydroquinolines.
Ghorai, Manas K.; Nanaji, Y.; Yadav, A. K.; Organic letters 13 (2011) 4256–4259; doi:10.1021/ol2016077

data_1502339
_publ_section_title
;
 Ring opening/C-N cyclization of activated aziridines with carbon
 nucleophiles: highly diastereo- and enantioselective synthesis of
 tetrahydroquinolines.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4256
_journal_page_last               4259
_journal_paper_doi               10.1021/ol2016077
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C26 H26 N2 O2 S1'
_chemical_formula_sum            'C26 H26 N2 O2 S'
_chemical_formula_weight         430.55
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 95.772(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   9.314(5)
_cell_length_b                   12.850(5)
_cell_length_c                   9.334(5)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.19
_cell_volume                     1111.5(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SAINT (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7229
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4991
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0173P)^2^+1.9510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                4516
_reflns_number_total             4991
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2016077_si_002.cif
_cod_data_source_block           15d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21
_cod_original_formula_sum        'C26 H26 N2 O2 S1'
_cod_database_code               1502339