Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars.
Malinowski, Maciej; Hensienne, Raphaël; Kern, Nicolas; Tardieu, Damien; Bodlenner, Anne; Hazelard, Damien; Compain, Philippe; Organic & biomolecular chemistry 16 (2018) 4688–4700; doi:10.1039/c8ob01065j

data_7156273
_publ_section_title
;
 Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a
 new class of iminosugars.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4688
_journal_page_last               4700
_journal_paper_doi               10.1039/c8ob01065j
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H15 N O4'
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.28
_chemical_name_systematic
(1S*,2S*,3S*,4S*,5S*)-6-butyl-5-(hydroxymethyl)-6-azabicyclo[3.2.0]heptane-2,3,4-triol
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-03-26 deposited with the CCDC.
2018-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.774(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2246(2)
_cell_length_b                   26.4216(12)
_cell_length_c                   8.1454(4)
_cell_measurement_reflns_used    5587
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.45
_cell_measurement_theta_min      3.35
_cell_volume                     1336.72(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.963
_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  0.0486
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10546
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.669
_diffrn_reflns_theta_min         3.345
_diffrn_source                   'Cu-ImuS microfocus tube'
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Flack x determined using 1438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.05(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4251
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0902
_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^)+(0.1082P)^2^+3.6223P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2406
_refine_ls_wR_factor_ref         0.2501
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.807
_reflns_Friedel_fraction_max     0.824
_reflns_number_gt                3514
_reflns_number_total             4251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01065j2.cif
_cod_data_source_block           pcnk170718
_cod_depositor_comments          'Adding full bibliography for 7156273.cif.'
_cod_database_code               7156273
_shelx_estimated_absorpt_t_min   0.762
_shelx_estimated_absorpt_t_max   0.908
_shelxl_version_number           2013-4
_shelx_res_checksum              45164