Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers.
Hu, Fang-Le; Wei, Yin; Shi, Min; Pindi, Suresh; Li, Guigen; Organic & biomolecular chemistry 11 (2013) 1921–1924; doi:10.1039/c3ob27495k

data_7152837
_publ_section_title
;
 Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis
 of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1921
_journal_page_last               1924
_journal_paper_doi               10.1039/c3ob27495k
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H25 Br N2 O4'
_chemical_formula_weight         485.37
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 117.709(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.4983(19)
_cell_length_b                   9.7453(10)
_cell_length_c                   14.3824(15)
_cell_measurement_reflns_used    2721
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.488
_cell_measurement_theta_min      4.492
_cell_volume                     2295.4(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6980
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    1.823
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32319
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.317
_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   0.006(8)
_refine_ls_extinction_coef       0.0024(4)
_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   0.970
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4201
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                3737
_reflns_number_total             4201
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob27495k.txt
_cod_data_source_block           cd212465
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
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_cod_original_sg_symbol_H-M      C2
_cod_database_code               7152837