The highly enantioselective Michael addition of ketones to nitrodienes catalyzed by the efficient organocatalyst system of pyrrolidinyl-thioimidazole and chiral thioureido acid.
Li, Zhao-Bo; Luo, Shu-Ping; Guo, Yi; Xia, Ai-Bao; Xu, Dan-Qian; Organic & biomolecular chemistry 8 (2010) 2505–2508; doi:10.1039/c002197k

data_7153341
_publ_section_title
;
 The highly enantioselective Michael addition of ketones to nitrodienes
 catalyzed by the efficient organocatalyst system of
 pyrrolidinyl-thioimidazole and chiral thioureido acid.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2505
_journal_page_last               2508
_journal_paper_doi               10.1039/c002197k
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C16 H18 Cl N O3 '
_chemical_formula_sum            'C16 H18 Cl N O3'
_chemical_formula_weight         307.78
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.5300(3)
_cell_length_b                   8.5175(6)
_cell_length_c                   34.0903(18)
_cell_measurement_reflns_used    9533
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.0
_cell_volume                     1605.71(17)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'CrystalStructure 3.7.0 (Rigaku,2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare,1999)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            15644
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             648.00
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.27
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1486 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.27(18)
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2148
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0320P)^2^+1.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1238
_reflns_number_gt                1391
_reflns_number_total             2148
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c002197k.txt
_cod_data_source_block           LZB-Cy-Cl
_cod_original_formula_sum        'C16 H18 Cl N O3 '
_cod_database_code               7153341