Asymmetric Syntheses of (-)-ADMJ and (+)-ADANJ: 2-Deoxy-2-amino Analogues of (-)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin.
Davies, Stephen G.; Figuccia, Aude L. A.; Fletcher Paul, Ai M.; Roberts, M.; Thomson, James E.; The Journal of organic chemistry 81 (2016) 6481–6495; doi:10.1021/acs.joc.6b01107

data_4036973
_publ_section_title
;
 Asymmetric Syntheses of (-)-ADMJ and (+)-ADANJ: 2-Deoxy-2-amino Analogues
 of (-)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6481
_journal_page_last               6495
_journal_paper_doi               10.1021/acs.joc.6b01107
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H16 I1 N1 O1'
_chemical_formula_sum            'C12 H16 I N O'
_chemical_formula_weight         317.17
_space_group_IT_number           33
_space_group_name_Hall           'P -2n -2ac'
_space_group_name_H-M_alt        'P c 21 n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2n -2ac'
_symmetry_space_group_name_H-M   'P c 21 n'
_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            8
_cell_length_a                   9.9626(2)
_cell_length_b                   14.5776(4)
_cell_length_c                   17.0821(4)
_cell_measurement_reflns_used    2970
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     2480.85(10)
_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 0.986
_diffrn_measured_fraction_theta_max 0.985
_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       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5148
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         5.194
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.557
_exptl_absorpt_correction_T_max  0.56
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.95
_refine_diff_density_min         -0.78
_refine_ls_abs_structure_details 'Flack (1983), 2248 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.40(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.0005979
_refine_ls_shift/su_mean         0.0000400
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.62P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0618
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0618
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              18
_reflns_limit_k_min              -18
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                4427
_reflns_number_total             5148
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.39
_oxford_diffrn_Wilson_scale      12.39
_oxford_refine_ls_r_factor_ref   0.0379
_oxford_refine_ls_scale          0.29062(17)
_oxford_reflns_number_all        5148
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo6b01107_si_002.cif
_cod_data_source_block           38
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Direct' was changed
to 'direct' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_formula_sum        'C12 H16 I1 N1 O1'
_cod_database_code               4036973
_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) H   (  32,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE O   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 202,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 212,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE O   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,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                                                                             
;