Diastereoselective Reductive Nitro-Mannich Reactions
James C. Anderson; Alexander J. Blake; Paul J. Koovits; Gregory J. Stepney; Journal of Organic Chemistry 77 (2012) 4711–4724; doi:10.1021/jo300535h

data_4027203
_publ_section_title
;
 Diastereoselective Reductive Nitro-Mannich Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4711
_journal_page_last               4724
_journal_paper_doi               10.1021/jo300535h
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C23 H21 F3 N2 O5'
_chemical_formula_sum            'C23 H21 F3 N2 O5'
_chemical_formula_weight         462.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 98.359(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8003(8)
_cell_length_b                   15.5619(11)
_cell_length_c                   13.3428(10)
_cell_measurement_reflns_used    7625
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_cell_volume                     2218.7(3)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2003)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2003)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material
'enCIFer (Allen et al., 2004); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_av_sigmaI/netI    0.050
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13862
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.95
_exptl_crystal_size_mid          0.93
_exptl_crystal_size_min          0.75
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.25
_refine_diff_density_rms         0.06
_refine_ls_extinction_coef       0.0069(15)
_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   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.086P)^2^+0.221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.132
_refine_ls_wR_factor_ref         0.137
_reflns_number_gt                4310
_reflns_number_total             5047
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo300535h_si_003.cif
_cod_data_source_block           nitfur
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027203