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_4026380
_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_absolute_configuration syn
_chemical_formula_moiety         'C17 H27 Cu N3 O6, H2 O'
_chemical_formula_sum            'C17 H29 Cu N3 O7'
_chemical_formula_weight         450.97
_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
_cell_angle_beta                 101.047(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3920(3)
_cell_length_b                   17.8921(13)
_cell_length_c                   8.0290(8)
_cell_measurement_reflns_used    13280
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      1
_cell_volume                     1042.23(14)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1158
_diffrn_reflns_av_sigmaI/netI    0.0803
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13235
_diffrn_reflns_theta_full        27.30
_diffrn_reflns_theta_max         27.30
_diffrn_reflns_theta_min         2.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.090
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.735
_refine_diff_density_min         -1.083
_refine_diff_density_rms         0.153
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4461
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+2.7429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                4046
_reflns_number_total             4461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200703j_si_004.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1042.22(14)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026380