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_1555474
_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 ad
_chemical_formula_sum            'C17 H22 N O3 S'
_chemical_formula_weight         320.41
_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                 90.369(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5345(4)
_cell_length_b                   8.8037(4)
_cell_length_c                   11.0062(7)
_cell_measurement_reflns_used    2189
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      28.3030
_cell_measurement_theta_min      3.8060
_cell_volume                     826.94(8)
_computing_cell_refinement
;
'Mon Jun 08 17:28:40 2015'
;
_computing_data_collection
;
'Mon Jun 08 17:28:40 2015'
;
_computing_data_reduction
;
'Mon Jun 08 17:28:40 2015'
;
_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 0.996
_diffrn_measured_fraction_theta_max 0.886
_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  0.0250
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6909
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.367
_diffrn_reflns_theta_min         3.703
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'Mon Jun 08 17:28:40 2015'
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             342
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1161 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0734P)^2^+0.3254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1409
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.766
_reflns_number_gt                3103
_reflns_number_total             3766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03209_si_002.cif
_cod_data_source_block           rc_1b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555474
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.903
_shelx_estimated_absorpt_t_max   0.960
_shelx_res_checksum              27758
_shelx_hkl_checksum              64784