A new class of structurally rigid tricyclic chiral secondary amine organocatalyst: highly enantioselective organocatalytic Michael addition of aldehydes to vinyl sulfones.
Xiao, Jian; Lu, Yun-Peng; Liu, Yan-Ling; Wong, Poh-Shen; Loh, Teck-Peng; Organic letters 13 (2011) 876–879; doi:10.1021/ol102933q

data_1501933
_publ_section_title
;
 A new class of structurally rigid tricyclic chiral secondary amine
 organocatalyst: highly enantioselective organocatalytic Michael addition
 of aldehydes to vinyl sulfones.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              876
_journal_page_last               879
_journal_paper_doi               10.1021/ol102933q
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H24 O5 S2'
_chemical_formula_sum            'C19 H24 O5 S2'
_chemical_formula_weight         396.50
_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                 94.556(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3787(17)
_cell_length_b                   10.986(2)
_cell_length_c                   20.823(4)
_cell_measurement_reflns_used    483
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      17.57
_cell_measurement_theta_min      2.70
_cell_volume                     1910.7(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.2011
_diffrn_reflns_av_sigmaI/netI    0.3775
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26262
_diffrn_reflns_theta_full        30.65
_diffrn_reflns_theta_max         30.65
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.9939
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.820
_refine_diff_density_rms         0.199
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         11437
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.2896
_refine_ls_R_factor_gt           0.0905
_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^)+(0.0959P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1734
_refine_ls_wR_factor_ref         0.2884
_reflns_number_gt                3686
_reflns_number_total             11437
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102933q_si_003.cif
_cod_data_source_block           p21
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1910.7(7)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1501933