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_4027021
_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_sum            'C16 H17 N O6'
_chemical_formula_weight         319.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.5870(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.75079(14)
_cell_length_b                   17.8174(3)
_cell_length_c                   11.3873(2)
_cell_measurement_temperature    123(2)
_cell_volume                     1567.54(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17565
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         4.62
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  0.8868
_exptl_absorpt_correction_T_min  0.7845
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0418P)^2^+0.4988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                2638
_reflns_number_total             2874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202489v_si_004.cif
_cod_data_source_block           shelxl
_cod_database_code               4027021