Stereoselective Synthesis of 1-Nitrobicyclo[3.1.0]hexanes and Fused Isoxazoline-N-oxides from Primary Nitro Compounds
Akio Kamimura; Ryota Takeuchi; Kosuke Ikeda; Takaaki Moriyama; Michinori Sumimoto; Journal of Organic Chemistry 77 (2012) 2236–2245; doi:10.1021/jo202489v

data_4027025
_publ_contact_author_email       uno@dpc.ehime-u.ac.jp
_publ_contact_author_fax         +81-89-927-9610
_publ_contact_author_name        'Prof Hidemitsu Uno'
_publ_contact_author_phone       +81-89-927-9610
_publ_section_title
;
 Stereoselective Synthesis of 1-Nitrobicyclo[3.1.0]hexanes and Fused
 Isoxazoline-N-oxides from Primary Nitro Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2236
_journal_page_last               2245
_journal_paper_doi               10.1021/jo202489v
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C24 H29 N O6'
_chemical_formula_sum            'C24 H29 N O6'
_chemical_formula_weight         427.50
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.5719(18)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.0984(4)
_cell_length_b                   21.6451(13)
_cell_length_c                   17.4041(11)
_cell_measurement_reflns_used    16863
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.05
_cell_volume                     2242.3(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32146
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             912.00
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.010
_refine_diff_density_min         -0.850
_refine_ls_extinction_coef       0.016(5)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5055
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0945
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1941P)^2^+0.4501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3391
_reflns_number_gt                2732
_reflns_number_total             5055
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo202489v_si_008.cif
_cod_data_source_block           20110614
_cod_original_cell_volume        2242.3(3)
_cod_database_code               4027025