Enantioselective Michael addition of ketones to maleimides catalyzed by bifunctional monosulfonyl DPEN salt
Yu, Feng; Sun, Xiaomin; Jin, Zhichao; Wen, Shigang; Liang, Xinmiao; Ye, Jinxing; Chemical Communications 46 (2010) 4589–4591; doi:10.1039/c0cc00774a

data_7111741
_publ_section_title
;
 Enantioselective Michael addition of ketones to maleimides catalyzed by
 bifunctional monosulfonyl DPEN salt
;
_journal_issue                   25
_journal_name_full               'Chemical Communications'
_journal_page_first              4589
_journal_page_last               4591
_journal_paper_doi               10.1039/c0cc00774a
_journal_volume                  46
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H12 Br N O3'
_chemical_formula_weight         310.15
_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                   6.3371(16)
_cell_length_b                   11.773(3)
_cell_length_c                   17.660(5)
_cell_measurement_reflns_used    1966
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.103
_cell_measurement_theta_min      5.767
_cell_volume                     1317.6(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0637
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7214
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    3.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33881
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.237
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.048(14)
_refine_ls_extinction_coef       0.0041(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.902
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0597P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                1730
_reflns_number_total             2570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC00774Asup1.cif
_cod_data_source_block           cd201160
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7111741