Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes.
Zhou, Wen-Ming; Liu, Han; Du, Da-Ming; Organic letters 10 (2008) 2817–2820; doi:10.1021/ol800945e

data_1504729
_publ_section_title
;
 Organocatalytic highly enantioselective Michael addition of
 2-hydroxy-1,4-naphthoquinones to nitroalkenes.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2817
_journal_page_last               2820
_journal_paper_doi               10.1021/ol800945e
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H12 Br N O5'
_chemical_formula_sum            'C18 H12 Br N O5'
_chemical_formula_weight         402.20
_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                 91.75(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.870(2)
_cell_length_b                   8.6195(17)
_cell_length_c                   18.694(4)
_cell_measurement_reflns_used    23891
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     1589.6(6)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1233
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7032
_diffrn_reflns_theta_full        27.34
_diffrn_reflns_theta_max         27.34
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    2.616
_exptl_absorpt_correction_T_max  0.6503
_exptl_absorpt_correction_T_min  0.5844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi    8 March, 1995'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.028(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.608
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7032
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.608
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0411
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                4704
_reflns_number_total             7032
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800945e-file002.cif
_cod_data_source_block           8f
_cod_original_cell_volume        1589.6(5)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1504729