Synthesis of Enantiopure 2-C-Glycosyl-3-nitrochromenes
Raquel G. Soengas; Humberto Rodríguez-Solla; Artur M. S. Silva; Ricardo Llavona; Filipe A. Almeida Paz; Journal of Organic Chemistry 78 (2013) 12831–12836; doi:10.1021/jo4021634

data_4028872
_publ_contact_author_address
; Department of Chemistry
  University of Aveiro
  QOPNA
  3810-193
  Aveiro
  Portugal
;
_publ_contact_author_email       artur.silva@ua.pt
_publ_contact_author_fax         '+351 234 370084'
_publ_contact_author_name        'Professor Artur M. S. Silva'
_publ_contact_author_phone       '+351 234 370714'
_publ_section_title
;
 Synthesis of Enantiopure 2-C-Glycosyl-3-nitrochromenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12831
_journal_page_last               12836
_journal_paper_doi               10.1021/jo4021634
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C17 H20 Br N O8'
_chemical_formula_sum            'C17 H20 Br N O8'
_chemical_formula_weight         446.25
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '23 September 2013'
_audit_creation_method           'SHELXL-97, manual editing plus enCIFer'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8090(10)
_cell_length_b                   10.7205(9)
_cell_length_c                   17.2919(16)
_cell_measurement_reflns_used    9731
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      29.11
_cell_measurement_theta_min      2.36
_cell_volume                     1818.4(3)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'APEX2 2012.4 (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST '
_diffrn_measurement_method       '\w / \f scans'
_diffrn_radiation_monochromator  'Multi-layer x-ray mirror'
_diffrn_radiation_source         'Sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45489
_diffrn_reflns_theta_full        29.12
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         3.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.307
_exptl_absorpt_correction_T_max  0.9553
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_description       Needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0269
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.2007P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0624
_reflns_number_gt                4539
_reflns_number_total             4876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4021634_si_002.cif
_cod_data_source_block           5i
_cod_database_code               4028872