Highly Enantioselective Nitroaldol Reactions Catalyzed by Copper(II) Complexes Derived from Substituted 2-(Pyridin-2-yl)imidazolidin-4-one Ligands
Illia Panov; Pavel Drabina; Zdeňka Padělková; Petr Šim°unek; Miloš Sedlák; Journal of Organic Chemistry 76 (2011) 4787–4793; doi:10.1021/jo200703j

data_4026378
_publ_section_title
;
 Highly Enantioselective Nitroaldol Reactions Catalyzed by Copper(II)
 Complexes Derived from Substituted 2-(Pyridin-2-yl)imidazolidin-4-one
 Ligands
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4787
_journal_page_last               4793
_journal_paper_doi               10.1021/jo200703j
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C12 H17 N3 O'
_chemical_formula_sum            'C12 H17 N3 O'
_chemical_formula_weight         219.29
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2140(5)
_cell_length_b                   11.4761(6)
_cell_length_c                   9.3960(5)
_cell_measurement_reflns_used    8874
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      1
_cell_volume                     1209.20(11)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       '\f and \w scans to fill the Ewald sphere'
_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  0.2105
_diffrn_reflns_av_sigmaI/netI    0.0887
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8538
_diffrn_reflns_theta_full        26.68
_diffrn_reflns_theta_max         26.68
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_coef       0.025(4)
_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   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0959
_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^)+(0.0000P)^2^+2.7820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.1896
_reflns_number_gt                1319
_reflns_number_total             1542
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200703j_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4026378