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_7153106
_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 syn
_chemical_compound_source        'total synthesis'
_chemical_formula_moiety         'C13 H18 N3 O6'
_chemical_formula_sum            'C13 H18 N3 O6'
_chemical_formula_weight         312.30
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2bc 2'
_symmetry_space_group_name_H-M   'P 2 21 21'
_atom_sites_solution_hydrogens   difmap
_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                   6.17130(10)
_cell_length_b                   12.5187(3)
_cell_length_c                   19.7716(5)
_cell_measurement_reflns_used    1934
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1527.49(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK '
_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 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3392
_diffrn_reflns_theta_full        26.917
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         5.256
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.39
_refine_ls_extinction_coef       15.448
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9854
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         1992
_refine_ls_number_restraints     378
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.0005570
_refine_ls_shift/su_mean         0.0000484
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A\~0\~*T\~0\~(x)+A\~1\~*T\~1\~(x) ... +A\~n-1\~]*T\~n-1\~(x)]
where A\~i\~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)\^2\^]\^2\^
A\~i\~ are:
22.1 35.1 22.0 9.89 2.48
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1036
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.1036
_reflns_limit_h_max              8
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                1562
_reflns_number_total             2005
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.78
_oxford_diffrn_Wilson_scale      2.62
_oxford_refine_ls_r_factor_ref   0.0579
_oxford_refine_ls_scale          0.620(2)
_oxford_reflns_number_all        1992
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            c3ob41334a.txt
_cod_data_source_block           1Gulo
_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.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' 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 2 21 21 '
_cod_database_code               7153106
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, FIRST(U'S) UNTIL N(22)
CONT C(100,U[ISO]) UNTIL C(140)
REM CONT O(90,U[ISO]) O(110,U[ISO]) UNTIL C(140)
EQUIV PART(1001,OCC) PART(1002,OCC)
WEIGHT -1 PART(1002,OCC)
EQUIV C(100,U[ISO]) UNTIL C(140)
REM RIDE C(10,X'S) C(100,X'S)
REM RIDE C(10,U'S) C(100,U'S)
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 ( 133,X'S) H ( 132,X'S)
RIDE C ( 14,X'S) H ( 141,X'S) H ( 143,X'S) H ( 142,X'S)
RIDE C ( 15,X'S) H ( 151,X'S) H ( 153,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)
RIDE C ( 130,X'S) H (1303,X'S) H (1302,X'S) H (1301,X'S)
RIDE C ( 140,X'S) H (1401,X'S) H (1402,X'S) H (1403,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
SAME C(8) O(9) C(10) O(11) C(12) C(13) C(14) AND
CONT C(8) O(9) C(100) O(110) C(120) C(130) C(140)
REM SHIFTLIMIT START (DO NOT REMOVE THIS LINE)
LIMIT 0.01000000 U[ISO]
LIMIT 0.01000000 X
LIMIT 0.01000000 Y
LIMIT 0.01000000 Z
LIMIT 0.01000000 U[11]
LIMIT 0.01000000 U[22]
LIMIT 0.01000000 U[33]
LIMIT 0.01000000 U[12]
LIMIT 0.01000000 U[13]
LIMIT 0.01000000 U[23]
LIMIT 0.01000000 OCC
REM SHIFTLIMIT END (DO NOT REMOVE THIS LINE)
END
;