Asymmetric Synthesis of Bicyclic Nitrocyclopropanes from Primary Nitro Compounds and Stereoselective Formation of Tetrahydro-2H-cyclopenta[b]furans via Ring Expansion/Cyclization Reaction.
Kamimura, Akio; Moriyama, Takaaki; Ito, Yuji; Kawamoto, Takuji; Uno, Hidemitsu; The Journal of organic chemistry 81 (2016) 4664–4681; doi:10.1021/acs.joc.6b00566

data_4036802
_publ_section_title
;
 Asymmetric Synthesis of Bicyclic Nitrocyclopropanes from Primary Nitro
 Compounds and Stereoselective Formation of
 Tetrahydro-2H-cyclopenta[b]furans via Ring Expansion/Cyclization
 Reaction.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4664
_journal_page_last               4681
_journal_paper_doi               10.1021/acs.joc.6b00566
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H35 N O3 Si'
_chemical_formula_sum            'C18 H35 N O3 Si'
_chemical_formula_weight         341.56
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.143(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   11.1637(9)
_cell_length_b                   7.8135(6)
_cell_length_c                   12.2928(9)
_cell_measurement_reflns_used    5655
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.86
_cell_measurement_theta_min      3.77
_cell_volume                     1024.63(14)
_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      100
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'VariMax 40 kV 30 mA Rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19156
_diffrn_reflns_theta_full        68.18
_diffrn_reflns_theta_max         68.18
_exptl_absorpt_coefficient_mu    1.113
_exptl_absorpt_correction_T_max  0.875
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             376.00
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.200
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1557 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     128
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0712P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1407
_reflns_number_gt                3114
_reflns_number_total             3570
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo6b00566_si_002.cif
_cod_data_source_block           20110413
_cod_original_cell_volume        1024.64(14)
_cod_database_code               4036802