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_7156212
_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_absolute_configuration ad
_chemical_formula_moiety         'C34 H27 N O12 [+ solvent]'
_chemical_formula_sum            'C34 H27 N O12'
_chemical_formula_weight         641.56
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-01-01 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.990(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.9257(16)
_cell_length_b                   5.4551(6)
_cell_length_c                   21.093(2)
_cell_measurement_reflns_used    1879
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.10
_cell_measurement_theta_min      2.81
_cell_volume                     1708.0(3)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.1392
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17263
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.502
_diffrn_reflns_theta_min         1.596
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.8124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.578
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
; 
 Flack x determined using 900 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_coef       0.034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         6067
_refine_ls_number_restraints     471
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1668
_refine_ls_R_factor_gt           0.0789
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0970P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.2084
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                3117
_reflns_number_total             6067
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00477c2.cif
_cod_data_source_block           d14017_sq
_cod_depositor_comments
'Adding full bibliography for 7156210--7156212.cif.'
_cod_database_code               7156212
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              83532
_shelx_fab_checksum              48736