Remote Control of Axial Chirality: Aminocatalytic Desymmetrization of N-Arylmaleimides via Vinylogous Michael Addition.
Di Iorio, Nicola; Righi, Paolo; Mazzanti, Andrea; Mancinelli, Michele; Ciogli, Alessia; Bencivenni, Giorgio; Journal of the American Chemical Society 136 (2014) 10250–10253; doi:10.1021/ja505610k

data_4122226
_publ_contact_author
;
Prof. Dr. Andrea Mazzanti
University of Bologna
Department of Industrial Chemistry "Toso Montanari"
Viale Risorgimento 4
40136 Bologna
Italy
;
_publ_section_title
;
 Remote Control of Axial Chirality: Aminocatalytic Desymmetrization of
 N-Arylmaleimides via Vinylogous Michael Addition.
;
_journal_issue                   29
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10250
_journal_page_last               10253
_journal_paper_doi               10.1021/ja505610k
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H26 Br N O3'
_chemical_formula_weight         432.35
_chemical_name_common            'compound 3b'
_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_date             11/25/2013
_audit_creation_method           SHELXL-97
_audit_update_record             02/02/2014
_cell_angle_alpha                90.00
_cell_angle_beta                 105.279(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.636(2)
_cell_length_b                   9.2863(18)
_cell_length_c                   20.039(4)
_cell_measurement_temperature    296(2)
_cell_volume                     2088.8(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_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            21804
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    1.989
_exptl_absorpt_correction_T_max  0.5868
_exptl_absorpt_correction_T_min  0.5034
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         8145
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0620
_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^)+(0.1035P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1616
_reflns_number_gt                5839
_reflns_number_total             8145
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja505610k_si_002.cif
_cod_data_source_block           gb1984
_cod_depositor_comments          'Adding full bibliography for 4122226.cif.'
_cod_original_cell_volume        2088.9(7)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4122226