Allylic Azide Rearrangement in Tandem with Huisgen Cycloaddition for Stereoselective Annulation: Synthesis of C-Glycosyl Iminosugars.
Moynihan, Lorna; Chadda, Rekha; McArdle, Patrick; Murphy, Paul V.; Organic letters 17 (2015) 6226–6229; doi:10.1021/acs.orglett.5b03209

data_1555475
_publ_section_title
;
 Allylic Azide Rearrangement in Tandem with Huisgen Cycloaddition for
 Stereoselective Annulation: Synthesis of C-Glycosyl Iminosugars.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6226
_journal_page_last               6229
_journal_paper_doi               10.1021/acs.orglett.5b03209
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration
;
Absolute configuration has not been established by anomalous-dispersion effects in diffraction measurements on the crystal.
The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure.
;
_chemical_formula_sum            'C13 H18 N3 O4'
_chemical_formula_weight         280.30
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.617(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1187(2)
_cell_length_b                   15.5628(7)
_cell_length_c                   7.4298(3)
_cell_measurement_reflns_used    2075
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      29.1607
_cell_measurement_theta_min      3.0322
_cell_volume                     707.46(5)
_computing_cell_refinement
;
'Mon Jul 02 16:09:18 2012'
;
_computing_data_collection
;
'Mon Jul 02 16:09:18 2012'
;
_computing_data_reduction
;
'Mon Jul 02 16:09:18 2012'
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector_area_resol_mean 16.1048
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2681
_diffrn_reflns_point_group_measured_fraction_full 0.635
_diffrn_reflns_point_group_measured_fraction_max 0.634
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         3.038
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
crysalispro, oxford diffraction ltd.,
version 1.171.34.36 (release 02-08-2010 crysalis171 .net)
(compiled aug  2 2010,13:00:58)
empirical absorption correction using spherical harmonics,
 implemented in scale3 abspack scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             298
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1638
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0583P)^2^+0.0785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.221
_reflns_Friedel_fraction_full    0.241
_reflns_Friedel_fraction_max     0.239
_reflns_number_gt                1547
_reflns_number_total             1638
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03209_si_001.cif
_cod_data_source_block           lor1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555475
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              24766
_shelx_hkl_checksum              4409