Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds.
Zhang, Ji; Eisink, Niek N. H. M.; Witte, Martin D.; Minnaard, Adriaan J.; The Journal of organic chemistry 84 (2019) 516–525; doi:10.1021/acs.joc.8b01949

data_4036020
_publ_section_title
;
 Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine,
 and Related Compounds.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              516
_journal_page_last               525
_journal_paper_doi               10.1021/acs.joc.8b01949
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C9 H17 N O6'
_chemical_formula_weight         235.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6845(2)
_cell_length_b                   11.1866(2)
_cell_length_c                   20.2699(5)
_cell_measurement_reflns_used    9804
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.59
_cell_measurement_theta_min      4.51
_cell_volume                     2195.97(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30369
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.583
_diffrn_reflns_theta_min         4.362
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.3176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0604
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4365
_reflns_number_total             4453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01949_si_003.cif
_cod_data_source_block           cu_molan481_0m_a
_cod_database_code               4036020
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.684
_shelx_estimated_absorpt_t_max   0.887
_shelx_res_checksum              77967
_shelx_hkl_checksum              21765