Asymmetric synthesis of 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidines as potential glycosidase inhibitors.
Curtis, Kim L.; Evinson, Emma L.; Handa, Sandeep; Singh, Kuldip; Organic & biomolecular chemistry 5 (2007) 3544–3553; doi:10.1039/b711994a

data_7151184
_publ_section_title
;
 Asymmetric synthesis of
 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidines as potential
 glycosidase inhibitors.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3544
_journal_page_last               3553
_journal_paper_doi               10.1039/b711994a
_journal_volume                  5
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_sum            'C12 H16 Br N O4 S'
_chemical_formula_weight         350.23
_chemical_melting_point          439(2)
_chemical_name_common
;(2R,3R,4R)-1-(Toluene-4-sulfonyl)-2-hydroxymethyl-3-bromo-4-
hydroxypyrrolidine
;
_chemical_name_systematic
;
(2R,3R,4R)-1-(Toluene-4-sulfonyl)-2-hydroxymethyl-3-bromo-4-hydroxypyrrolidine
;
_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                   7.5443(6)
_cell_length_b                   10.6588(9)
_cell_length_c                   17.4366(15)
_cell_measurement_reflns_used    5920
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.24
_cell_volume                     1402.1(2)
_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      150(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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11010
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    3.089
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
absorption correction based on 8619 reflections (SADABS); Rint 0.032 before
correction and 0.027 after.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0255
_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^)+(0.0394P)^2^+0.0192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0661
_reflns_number_gt                2592
_reflns_number_total             2752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b711994a.txt
_cod_data_source_block           04058
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '437-441' was changed to '439(2)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7151184