Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D.
Saikia, Anil K.; Indukuri, Kiran; Das, Jagadish; Organic & biomolecular chemistry 12 (2014) 7026–7035; doi:10.1039/c4ob01130a

data_7153954
_publ_section_title
;
 Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza
 Prins reaction of endocyclic N-acyliminium ions: application to the total
 synthesis of (+-)-epi-indolizidine 167B and 209D.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7026
_journal_page_last               7035
_journal_paper_doi               10.1039/c4ob01130a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C25 H29 N O4 S'
_chemical_formula_weight         439.56
_space_group_IT_number           14
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_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 93.509(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.812(3)
_cell_length_b                   11.923(3)
_cell_length_c                   18.961(5)
_cell_measurement_reflns_used    1748
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.17
_cell_measurement_theta_min      2.81
_cell_volume                     2439.7(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
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_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8618
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_diffrn_reflns_theta_max         26.31
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0467
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                3734
_reflns_number_total             4921
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01130a3.cif
_cod_data_source_block           kiran
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7153954.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7153954