Asymmetric Syntheses of (-)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin via a Ring-Expansion Approach.
Davies, Stephen G.; Figuccia, Aude L. A.; Fletcher, Ai M.; Roberts, Paul M.; Thomson, James E.; Organic letters 15 (2013) 2042–2045; doi:10.1021/ol400735z

data_1511956
_publ_section_title
;
 Asymmetric Syntheses of (-)-1-Deoxymannojirimycin and
 (+)-1-Deoxyallonojirimycin via a Ring-Expansion Approach.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2042
_journal_page_last               2045
_journal_paper_doi               10.1021/ol400735z
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H26 Cl3 N1 O4'
_chemical_formula_sum            'C21 H26 Cl3 N O4'
_chemical_formula_weight         462.80
_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   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90.8174(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1676(4)
_cell_length_b                   8.2551(3)
_cell_length_c                   12.4524(5)
_cell_measurement_reflns_used    2713
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1147.87(7)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5050
_diffrn_reflns_theta_full        27.480
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         5.204
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.39
_refine_ls_abs_structure_details 'Flack (1983), 2261 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.09(12)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0257
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.0000987
_refine_ls_shift/su_mean         0.0000103
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F) + ( 0.01P)^2^ + 0.04P] 
 ,where P=(max(Fo,0) + 2Fc)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0998
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0622
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3081
_reflns_number_total             5050
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.23
_oxford_diffrn_Wilson_scale      6.24
_oxford_refine_ls_r_factor_ref   0.0508
_oxford_refine_ls_scale          0.4361(11)
_oxford_reflns_number_all        5050
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            ol400735z_si_001.cif
_cod_data_source_block           19.CHCl3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_formula_sum        'C21 H26 Cl3 N1 O4'
_cod_database_code               1511956