An approach to 8 stereoisomers of homonojirimycin from d-glucose via kinetic & thermodynamic azido-γ-lactones.
Glawar, Andreas F. G.; Jenkinson, Sarah F.; Newberry, Scott J.; Thompson, Amber L.; Nakagawa, Shinpei; Yoshihara, Akihide; Akimitsu, Kazuya; Izumori, Ken; Butters, Terry D.; Kato, Atsushi; Fleet, George W. J.; Organic & biomolecular chemistry 11 (2013) 6886–6899; doi:10.1039/c3ob41334a

data_7153107
_publ_section_title
;
 An approach to 8 stereoisomers of homonojirimycin from d-glucose via
 kinetic &amp; thermodynamic azido-\g-lactones.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6886
_journal_page_last               6899
_journal_paper_doi               10.1039/c3ob41334a
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_compound_source        'total synthesis'
_chemical_formula_moiety         'C13 H19 N3 O6'
_chemical_formula_sum            'C13 H19 N3 O6'
_chemical_formula_weight         313.31
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.36955(8)
_cell_length_b                   8.40431(11)
_cell_length_c                   24.1914(3)
_cell_measurement_reflns_used    11341
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     1498.32(3)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS '
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15552
_diffrn_reflns_theta_full        75.689
_diffrn_reflns_theta_max         75.689
_diffrn_reflns_theta_min         3.654
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.02(11)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0121
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0240
_refine_ls_shift/su_max          0.0009122
_refine_ls_shift/su_mean         0.0000612
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s\^2\^(F\^2\^) + ( 0.04P)\^2\^ + 0.18P]
,where P=(max(Fo\^2\^,0) + 2Fc\^2\^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0623
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0623
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                3017
_reflns_number_total             3093
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.35
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0246
_oxford_refine_ls_scale          7.08(13)
_oxford_reflns_number_all        3092
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c3ob41334a.txt
_cod_data_source_block           2Ido
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               7153107
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
CONT ENANTIO
RIDE C ( 2,X'S) H ( 21,X'S)
RIDE C ( 3,X'S) H ( 31,X'S)
RIDE C ( 7,X'S) H ( 71,X'S)
RIDE C ( 8,X'S) H ( 81,X'S)
RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S)
RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S) H ( 133,X'S)
RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) H ( 143,X'S)
RIDE C ( 15,X'S) H ( 153,X'S) H ( 151,X'S) H ( 152,X'S)
RIDE C ( 16,X'S) H ( 161,X'S) H ( 163,X'S) H ( 162,X'S)
RIDE C ( 17,X'S) H ( 171,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;