Asymmetric Michael additions of α-nitrocyclohexanone to aryl nitroalkenes catalyzed by natural amino acid-derived bifunctional thioureas.
Jörres, Manuel; Schiffers, Ingo; Atodiresei, Iuliana; Bolm, Carsten; Organic letters 14 (2012) 4518–4521; doi:10.1021/ol302005f

data_1508620
_publ_section_title
;
 Asymmetric Michael additions of \a-nitrocyclohexanone to aryl
 nitroalkenes catalyzed by natural amino acid-derived bifunctional
 thioureas.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4518
_journal_page_last               4521
_journal_paper_doi               10.1021/ol302005f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C14 H15 Cl N2 O5'
_chemical_formula_weight         326.73
_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   geom
_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            4
_cell_length_a                   8.5616(3)
_cell_length_b                   13.1029(3)
_cell_length_c                   13.4976(4)
_cell_measurement_reflns_used    7435
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.85
_cell_measurement_theta_min      4.70
_cell_volume                     1514.18(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9804
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         4.70
_exptl_absorpt_coefficient_mu    2.476
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.4407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.025(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                2585
_reflns_number_total             2660
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302005f_si_002.cif
_cod_data_source_block           cu_ia0013_0m
_cod_original_cell_volume        1514.19(8)
_cod_original_sg_symbol_H-M      p_21_21_21
_cod_database_code               1508620