Catalytic Enantioselective Protonation of Nitronates Utilizing an Organocatalyst Chiral Only at Sulfur
Kyle L. Kimmel; Jimmie D. Weaver; Melissa Lee; Jonathan A. Ellman; Journal of the American Chemical Society 134 (2012) 9058–9061; doi:10.1021/ja3026196

data_4118012
_publ_section_title
;
 Catalytic Enantioselective Protonation of Nitronates Utilizing an
 Organocatalyst Chiral Only at Sulfur
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9058
_journal_page_last               9061
_journal_paper_doi               10.1021/ja3026196
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C10 H15 N O6'
_chemical_formula_weight         245.23
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.536(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8901(7)
_cell_length_b                   11.4722(11)
_cell_length_c                   12.9352(12)
_cell_measurement_reflns_used    8520
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.42
_cell_volume                     1170.43(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9004
_diffrn_reflns_theta_full        66.00
_diffrn_reflns_theta_max         68.15
_diffrn_reflns_theta_min         3.42
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  0.9248
_exptl_absorpt_correction_T_min  0.7616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       blade
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                3465
_reflns_number_total             3480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3026196_si_001.cif
_cod_data_source_block           ellm07
_cod_database_code               4118012