Chiral Bis(imidazolidine)pyridine-Cu(OTf)2: Catalytic Asymmetric Endo-Selective [3 + 2] Cycloaddition of Imino Esters with Nitroalkenes
Takayoshi Arai; Asami Mishiro; Naota Yokoyama; Kuniko Suzuki; Hiroyasu Sato; Journal of the American Chemical Society 132 (2010) 5338–5339; doi:10.1021/ja100265j

data_4102274
_publ_contact_author_email       tarai@faculty.chiba-u.jp
_publ_contact_author_fax         +81-43-290-2889
_publ_contact_author_name        'Takayoshi Arai'
_publ_section_title
;
 Chiral Bis(imidazolidine)pyridine-Cu(OTf)2: Catalytic Asymmetric
 Endo-Selective [3 + 2] Cycloaddition of Imino Esters with Nitroalkenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5338
_journal_page_last               5339
_journal_paper_doi               10.1021/ja100265j
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_moiety
'2(C49 H47 Cu N5 O),4(C1 F3 O3 S), C7 H8, 2.35(H2 O)'
_chemical_formula_sum            'C109 H106.7 Cu2 F12 N10 O16.35 S4'
_chemical_formula_weight         2301.71
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_audit_creation_date             2009-10-23
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                87.917(3)
_cell_angle_beta                 82.601(3)
_cell_angle_gamma                89.810(4)
_cell_formula_units_Z            1
_cell_length_a                   9.6860(12)
_cell_length_b                   11.3379(15)
_cell_length_c                   24.442(3)
_cell_measurement_reflns_used    8558
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     2660.1(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      93.1
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            42739
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1191.50
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.18
_refine_diff_density_min         -0.90
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  11537 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.022(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     1277
_refine_ls_number_reflns         23693
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0979P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                18164
_reflns_number_total             23693
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja100265j_si_001.cif
_cod_data_source_block           '__PyBidineCuOTf2'
_cod_original_formula_sum        'C109 H106.70 Cu2 F12 N10 O16.35 S4 '
_cod_database_code               4102274