Total synthesis of ent-calystegine B4 via nitro-Michael/aldol reaction.
Kamimura, Akio; Miyazaki, Koichiro; Suzuki, Shuzo; Ishikawa, Shingo; Uno, Hidemitsu; Organic & biomolecular chemistry 10 (2012) 4362–4366; doi:10.1039/c2ob25386k

data_7152382
_publ_section_title
;
 Total synthesis of ent-calystegine B4 via nitro-Michael/aldol reaction.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4362
_journal_page_last               4366
_journal_paper_doi               10.1039/c2ob25386k
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C10 H15 N O6 '
_chemical_formula_sum            'C10 H15 N O6'
_chemical_formula_weight         245.23
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4247(7)
_cell_length_b                   9.3395(9)
_cell_length_c                   16.7423(15)
_cell_measurement_reflns_used    5148
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1160.96(19)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8.2'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Mercury-7'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode (50 kV, 200 mA)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13109
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+0.2426P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0833
_reflns_number_gt                1492
_reflns_number_total             1541
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25386k.txt
_cod_data_source_block           '__SS01089'
_cod_original_formula_sum        'C10 H15 N O6 '
_cod_database_code               7152382