Versatile Intramolecular Aza-Prins and Prins Cyclization of Aryl Epoxides: A Facile Synthesis of Diaza-, Oxa-aza-, and Dioxa-bicycles
Jillu S. Yadav; Prashant Borkar; P. Pawan Chakravarthy; Basi V. Subba Reddy; Akella V. S. Sarma; Shaik Jeelani Basha; Balasubramanian Sridhar; René Grée; Journal of Organic Chemistry 75 (2010) 2081–2084; doi:10.1021/jo902683p

data_4025312
_publ_section_title
;
 Versatile Intramolecular Aza-Prins and Prins Cyclization of Aryl
 Epoxides: A Facile Synthesis of Diaza-, Oxa-aza-, and Dioxa-bicycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2081
_journal_page_last               2084
_journal_paper_doi               10.1021/jo902683p
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C28 H31 Cl N2 O4 S2'
_chemical_formula_sum            'C28 H31 Cl N2 O4 S2'
_chemical_formula_weight         559.12
_chemical_name_systematic
; 
(3aS,4R,7aS)-4-(4-chlorobenzyl)-octahydro-1,5-ditosyl-1H-pyrrolo[3,2-c]Pyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 95.222(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4417(7)
_cell_length_b                   11.5112(9)
_cell_length_c                   25.0215(18)
_cell_measurement_reflns_used    4834
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.58
_cell_measurement_theta_min      2.59
_cell_volume                     2708.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25615
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0639
_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^)+(0.0547P)^2^+1.6987P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                4006
_reflns_number_total             4771
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo902683p_si_001_1.cif
_cod_data_source_block           ag44m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4025312