Enantioselective synthesis of dihydropyridinones via NHC-catalyzed aza-Claisen reaction.
Wanner, Benedikt; Mahatthananchai, Jessada; Bode, Jeffrey W.; Organic letters 13 (2011) 5378–5381; doi:10.1021/ol202272t

data_1502505
_publ_section_title
;
 Enantioselective synthesis of dihydropyridinones via NHC-catalyzed
 aza-Claisen reaction.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5378
_journal_page_last               5381
_journal_paper_doi               10.1021/ol202272t
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         '2(C13 H11 Br N2 O) , C4 H8 O2'
_chemical_formula_sum            'C28 H26 Br2 N4 O3'
_chemical_formula_weight         626.35
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.246(2)
_cell_angle_beta                 84.746(2)
_cell_angle_gamma                79.465(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7053(4)
_cell_length_b                   13.2135(7)
_cell_length_c                   13.4615(8)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.69
_cell_volume                     1307.17(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Platon, Ortep'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement
'OLEX2 (Dolomanov, 2009), SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18568
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    3.139
_exptl_absorpt_correction_T_max  0.7045
_exptl_absorpt_correction_T_min  0.5196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     850
_refine_ls_number_reflns         8806
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.002
_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          0.0485
_refine_ls_wR_factor_ref         0.0498
_reflns_number_gt                7975
_reflns_number_total             8806
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202272t_si_002.cif
_cod_data_source_block           jb050811
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P1
_cod_database_code               1502505