Double diastereocontrol in bifunctional thiourea organocatalysis: iterative Michael-Michael-Henry sequence regulated by the configuration of chiral catalysts.
Varga, Szilárd; Jakab, Gergely; Drahos, László; Holczbauer, Tamás; Czugler, Mátyás; Soós, Tibor; Organic letters 13 (2011) 5416–5419; doi:10.1021/ol201559j

data_1502324
_publ_section_title
;
 Double diastereocontrol in bifunctional thiourea organocatalysis:
 iterative Michael-Michael-Henry sequence regulated by the configuration
 of chiral catalysts.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5416
_journal_page_last               5419
_journal_paper_doi               10.1021/ol201559j
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 N2 O5,  0.25(C7 H4 Br O2)'
_chemical_formula_sum            'C25.75 H23 Br0.25 N2 O5.5'
_chemical_formula_weight         468.44
_chemical_name_common            'l-8a.p-Br-benzoic acid 1:0.25 clathrate'
_chemical_name_systematic
; 
 ? 
;
_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                90.00
_cell_angle_beta                 93.510(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.505(3)
_cell_length_b                   6.1813(11)
_cell_length_c                   15.804(3)
_cell_measurement_reflns_used    18601
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      21.36
_cell_measurement_theta_min      2.38
_cell_volume                     1316.8(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_molecular_graphics    'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_computing_publication_material  'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      108(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'R-AXIS RAPID'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal focus sealed tube'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56089
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_av_sigmaI/netI    0.0727
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26713
_diffrn_reflns_theta_full        17.74
_diffrn_reflns_theta_max         17.74
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  0.799
_exptl_absorpt_correction_T_min  0.354
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.304
_refine_diff_density_max         1.18
_refine_diff_density_min         -0.47
_refine_diff_density_rms         0.12
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     86
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0971
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2565
_refine_ls_wR_factor_ref         0.2759
_reflns_number_gt                2593
_reflns_number_total             3541
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201559j_si_001.cif
_cod_data_source_block           al30
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C25.75 H23 Br0.25 N2 O5.50'
_cod_database_code               1502324