On the [3 + 2] Annulation of Cyclic Allylsilanes with N-Phenyltriazolinedione: An Enantio- and Diastereoselective Synthesis of cis-1,3-Diaminocyclitols
Raudra T. Dey; Tarun K. Sarkar; Journal of Organic Chemistry 75 (2010) 4521–4529; doi:10.1021/jo100724w

data_4025516
_publ_contact_author_address
;Department of Chemistry
IIT-Kharagpur, 721302
Kharagpur
INDIA
;
_publ_contact_author_email       tksr@chem.iitkgp.ernet.in
_publ_contact_author_fax         '+91-3222-255303 '
_publ_contact_author_name        'Prof. Tarun K. Sarkar'
_publ_contact_author_phone       +91-3222-283330
_publ_section_title
;
 On the [3 + 2] Annulation of Cyclic Allylsilanes with
 N-Phenyltriazolinedione: An Enantio- and Diastereoselective Synthesis of
 cis-1,3-Diaminocyclitols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4521
_journal_page_last               4529
_journal_paper_doi               10.1021/jo100724w
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_formula_sum            'C22 H25 N3 O4 Si'
_chemical_formula_weight         423.54
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.746(3)
_cell_length_b                   8.817(3)
_cell_length_c                   32.078(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2190.8(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.2127
_diffrn_reflns_av_sigmaI/netI    0.1298
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17025
_diffrn_reflns_theta_full        20.94
_diffrn_reflns_theta_max         20.94
_diffrn_reflns_theta_min         1.27
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                1782
_reflns_number_total             2316
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100724w_si_002.cif
_cod_data_source_block           tksrtd_03_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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_cell_volume        2190.9(10)
_cod_database_code               4025516