Chiral 2-Aminobenzimidazoles as Recoverable Organocatalysts for the Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes
Diana Almaşi; Diego A. Alonso; Enrique Gómez-Bengoa; Carmen Nájera; Journal of Organic Chemistry 74 (2009) 6163–6168; doi:10.1021/jo9010552

data_4024763
_publ_section_title
;
Chiral 2-Aminobenzimidazoles as Recoverable Organocatalysts for the
Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6163
_journal_page_last               6168
_journal_paper_doi               10.1021/jo9010552
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C15 H22 N4'
_chemical_formula_sum            'C15 H22 N4'
_chemical_formula_weight         258.37
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8067(12)
_cell_length_b                   14.7475(13)
_cell_length_c                   16.7683(15)
_cell_measurement_reflns_used    4503
_cell_measurement_temperature    298(1)
_cell_measurement_theta_max      19.8
_cell_measurement_theta_min      2.4
_cell_volume                     3167.0(5)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR92 (Altomare, Cascarano, Giacovazzo & Guagliardi, 1993)'
_diffrn_ambient_temperature      298(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32161
_diffrn_reflns_theta_full        27.61
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.093
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.025
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.0961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                2794
_reflns_number_total             4096
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo9010552_si_001.cif
_cod_data_source_block           x
_cod_database_code               4024763