α-Geminal Dihydroxymethyl Piperidine and Pyrrolidine Iminosugars: Synthesis, Conformational Analysis, Glycosidase Inhibitory Activity, and Molecular Docking Studies
Nitin J. Pawar; Vijay Singh Parihar; Sanjay T. Chavan; Rakesh Joshi; Pranaya V. Joshi; Sushma G. Sabharwal; Vedavati G. Puranik; Dilip D. Dhavale; Journal of Organic Chemistry 77 (2012) 7873–7882; doi:10.1021/jo3009534

data_4027485
_publ_section_title
;
 \a-Geminal Dihydroxymethyl Piperidine and Pyrrolidine Iminosugars:
 Synthesis, Conformational Analysis, Glycosidase Inhibitory Activity, and
 Molecular Docking Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7873
_journal_page_last               7882
_journal_paper_doi               10.1021/jo3009534
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C24 H28 Cl2 O6'
_chemical_formula_sum            'C24 H28 Cl2 O6'
_chemical_formula_weight         483.36
_chemical_name_common            iminosugars
_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                 108.327(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.299(1)
_cell_length_b                   39.634(8)
_cell_length_c                   9.864(2)
_cell_measurement_reflns_used    4582
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      2.17
_cell_volume                     2337.7(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0928
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15488
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         7150
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.185
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0841
_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^+7.8642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1729
_reflns_number_gt                6264
_reflns_number_total             7150
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3009534_si_003.cif
_cod_data_source_block           C24H28Cl2O6compound5a
_cod_original_cell_volume        2337.7(9)
_cod_database_code               4027485