Synthesis of multibranched australine derivatives from reducing castanospermine analogues through the Amadori rearrangement of gem-diamine intermediates: selective inhibitors of β-glucosidase.
Sánchez-Fernández, Elena M; Álvarez, Eleuterio; Ortiz Mellet, Carmen; García Fernández, José M; The Journal of organic chemistry 79 (2014) 11722–11728; doi:10.1021/jo5025283

data_4030219
_publ_section_title
;
 Synthesis of multibranched australine derivatives from reducing
 castanospermine analogues through the Amadori rearrangement of
 gem-diamine intermediates: selective inhibitors of \b-glucosidase.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11722
_journal_page_last               11728
_journal_paper_doi               10.1021/jo5025283
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H28 N2 O5'
_chemical_formula_sum            'C15 H28 N2 O5'
_chemical_formula_weight         316.39
_space_group_IT_number           4
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_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                 100.167(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.836(2)
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_cell_length_c                   16.037(5)
_cell_measurement_reflns_used    2930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.28
_cell_measurement_theta_min      2.58
_cell_volume                     845.7(4)
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
 Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_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  0.0669
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13814
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         1.29
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_correction_T_min  0.9926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
program SADABS, Bruker (2001).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.08
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_refine_diff_density_max         0.458
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 731 Friedels pairs'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         1861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0981P)^2^+1.0110P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1718
_reflns_number_gt                1506
_reflns_number_total             1861
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5025283_si_002.cif
_cod_data_source_block           19
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030219.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4030219