Protecting group directed diversity during Mitsunobu cyclization of a carbohydrate derived diamino triol. Synthesis of novel bridged bicyclic and six-membered iminocyclitols.
Ganesan, Muthupandian; Salunke, Rahul Vilas; Singh, Nem; Ramesh, Namakkal G.; Organic & biomolecular chemistry 11 (2013) 599–611; doi:10.1039/c2ob27000e

data_7152792
_publ_section_title
;
 Protecting group directed diversity during Mitsunobu cyclization of a
 carbohydrate derived diamino triol. Synthesis of novel bridged bicyclic
 and six-membered iminocyclitols.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              599
_journal_page_last               611
_journal_paper_doi               10.1039/c2ob27000e
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H24 N2 O6 S2'
_chemical_formula_sum            'C20 H24 N2 O6 S2'
_chemical_formula_weight         452.55
_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                90.00
_cell_angle_beta                 96.651(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.043(3)
_cell_length_b                   8.990(2)
_cell_length_c                   25.768(6)
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.78
_cell_volume                     2310.8(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0821
_diffrn_reflns_av_sigmaI/netI    0.0905
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            22440
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952.0
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.152
_refine_diff_density_max         1.600
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.139
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         8130
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0846
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1476P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2269
_refine_ls_wR_factor_ref         0.2399
_reflns_number_gt                5053
_reflns_number_total             8130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob27000e.txt
_cod_data_source_block           NGR2
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2310.9(10)
_cod_original_sg_symbol_Hall     P2yb
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7152792