D-glucosamine trimethylene dithioacetal derivatives: formation of six- and seven-membered ring amino carbasugars. Synthesis of (-)-calystegine B3.
Chen, Yue-Lei; Redlich, Hartmut; Bergander, Klaus; Fröhlich, Roland; Organic & biomolecular chemistry 5 (2007) 3330–3339; doi:10.1039/b711112f

data_7151177
_publ_section_title
;
 D-glucosamine trimethylene dithioacetal derivatives: formation of six-
 and seven-membered ring amino carbasugars. Synthesis of
 (-)-calystegine B3.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3330
_journal_page_last               3339
_journal_paper_doi               10.1039/b711112f
_journal_volume                  5
_journal_year                    2007
_chemical_formula_sum            'C15 H22 F3 N O6 S2'
_chemical_formula_weight         433.46
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_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            8
_cell_length_a                   9.905(1)
_cell_length_b                   9.905(1)
_cell_length_c                   39.488(1)
_cell_measurement_reflns_used    5012
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.60
_cell_measurement_theta_min      0.88
_cell_volume                     3874.1(6)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            24194
_diffrn_reflns_theta_full        66.40
_diffrn_reflns_theta_max         66.40
_diffrn_reflns_theta_min         4.48
_exptl_absorpt_coefficient_mu    3.055
_exptl_absorpt_correction_T_max  0.6572
_exptl_absorpt_correction_T_min  0.4144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.927
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0891P)^2^+2.3141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                2802
_reflns_number_total             2937
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b711112f.txt
_cod_data_source_block           red3679
_cod_original_sg_symbol_H-M      P41212
_cod_database_code               7151177