Glycosyl nitrates in synthesis: streamlined access to glucopyranose building blocks differentiated at C-2.
Wang, Tinghua; Nigudkar, Swati S.; Yasomanee, Jagodige P.; Rath, Nigam P.; Stine, Keith J.; Demchenko, Alexei V.; Organic & biomolecular chemistry 16 (2018) 3596–3604; doi:10.1039/c8ob00477c

data_7156210
_publ_section_title
;
 Glycosyl nitrates in synthesis: streamlined access to glucopyranose
 building blocks differentiated at C-2.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3596
_journal_page_last               3604
_journal_paper_doi               10.1039/c8ob00477c
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'Ce H4 N5 O17, 2(H2 O), 2(N H4)'
_chemical_formula_sum            'Ce H16 N7 O19'
_chemical_formula_weight         558.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-01 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.8202(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0806(4)
_cell_length_b                   8.8522(4)
_cell_length_c                   17.7829(6)
_cell_measurement_reflns_used    5054
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.17
_cell_measurement_theta_min      2.35
_cell_volume                     1700.80(11)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4419
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.304
_diffrn_reflns_theta_min         2.349
_exptl_absorpt_coefficient_mu    2.790
_exptl_absorpt_correction_T_max  0.438258
_exptl_absorpt_correction_T_min  0.344314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS Version 2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1100
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.075
_refine_diff_density_max         1.057
_refine_diff_density_min         -1.251
_refine_diff_density_rms         0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4419
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+20.6965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4001
_reflns_number_total             4419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00477c2.cif
_cod_data_source_block           a16316t5
_cod_depositor_comments
'Adding full bibliography for 7156210--7156212.cif.'
_cod_database_code               7156210
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.567
_shelx_estimated_absorpt_t_max   0.818
_shelx_res_checksum              95697