Iminosugar C-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic Iminosugars.
Prasad, Sure Siva; Senthilkumar, Soundararasu; Srivastava, Akriti; Baskaran, Sundarababu; Organic letters 19 (2017) 4403–4406; doi:10.1021/acs.orglett.7b02175

data_1547089
_publ_section_title
;
 Iminosugar C-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic
 Iminosugars.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4403
_journal_page_last               4406
_journal_paper_doi               10.1021/acs.orglett.7b02175
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H25 N3 O7 S'
_chemical_formula_sum            'C19 H25 N3 O7 S'
_chemical_formula_weight         439.48
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                95.115(2)
_cell_angle_beta                 90.454(2)
_cell_angle_gamma                97.456(2)
_cell_formula_units_Z            2
_cell_length_a                   5.8603(2)
_cell_length_b                   8.7507(3)
_cell_length_c                   19.9834(6)
_cell_measurement_reflns_used    6906
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      2.36
_cell_volume                     1011.87(6)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13391
_diffrn_reflns_point_group_measured_fraction_full 0.848
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.023
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (bruker, 2004)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2164 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         6034
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0537P)^2^+0.2836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.705
_reflns_Friedel_fraction_max     0.705
_reflns_number_gt                5618
_reflns_number_total             6034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02175_si_002.cif
_cod_data_source_block           525
_cod_database_code               1547089
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              92723
_shelx_hkl_checksum              88436