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_1511955
_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         'C28 H33 N1 O3'
_chemical_formula_sum            'C28 H33 N O3'
_chemical_formula_weight         431.57
_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                 109.357(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.8417(4)
_cell_length_b                   6.65220(10)
_cell_length_c                   14.8628(5)
_cell_measurement_reflns_used    6421
_cell_measurement_temperature    150
_cell_measurement_theta_max      85
_cell_measurement_theta_min      3
_cell_volume                     1197.89(6)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14135
_diffrn_reflns_theta_full        68.915
_diffrn_reflns_theta_max         80.134
_diffrn_reflns_theta_min         3.151
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.28
_refine_ls_abs_structure_details 'Flack (1983), 2142 Friedel-pairs'
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9380
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.0001163
_refine_ls_shift/su_mean         0.0000172
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.42P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1101
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.1101
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3915
_reflns_number_total             4855
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.63
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0469
_oxford_refine_ls_scale          6.96(15)
_oxford_reflns_number_all        4265
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ol400735z_si_001.cif
_cod_data_source_block           13
_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        'C28 H33 N1 O3'
_cod_database_code               1511955