Organocatalytic asymmetric tandem Michael-Henry reactions: a highly stereoselective synthesis of multifunctionalized cyclohexanes with two quaternary stereocenters.
Tan, Bin; Chua, Pei Juan; Li, Yongxin; Zhong, Guofu; Organic letters 10 (2008) 2437–2440; doi:10.1021/ol8007183

data_1504690
_publ_section_title
;
 Organocatalytic asymmetric tandem Michael-Henry reactions: a highly
 stereoselective synthesis of multifunctionalized cyclohexanes with two
 quaternary stereocenters.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2437
_journal_page_last               2440
_journal_paper_doi               10.1021/ol8007183
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H22 Br N O6'
_chemical_formula_sum            'C18 H22 Br N O6'
_chemical_formula_weight         428.28
_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                 107.225(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2367(2)
_cell_length_b                   13.9546(4)
_cell_length_c                   8.6506(2)
_cell_measurement_reflns_used    4781
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      29.80
_cell_measurement_theta_min      2.59
_cell_volume                     949.70(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11264
_diffrn_reflns_theta_full        31.09
_diffrn_reflns_theta_max         31.09
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    2.198
_exptl_absorpt_correction_T_max  0.6206
_exptl_absorpt_correction_T_min  0.5585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5870
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.825
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0642
_reflns_number_gt                4866
_reflns_number_total             5870
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8007183-file003.cif
_cod_data_source_block           zgf27
_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_sg_symbol_H-M      P2(1)
_cod_database_code               1504690