Enantioselective Diels-Alder Reaction of 1,2-Dihydropyridines with Aldehydes Using β-Amino Alcohol Organocatalyst.
Kohari, Yoshihito; Okuyama, Yuko; Kwon, Eunsang; Furuyama, Taniyuki; Kobayashi, Nagao; Otuki, Teppei; Kumagai, Jun; Seki, Chigusa; Uwai, Koji; Dai, Gang; Iwasa, Tatsuo; Nakano, Hiroto; The Journal of organic chemistry 79 (2014) 9500–9511; doi:10.1021/jo501433c

data_4030027
_publ_section_title
;
 Enantioselective Diels-Alder Reaction of 1,2-Dihydropyridines with
 Aldehydes Using \b-Amino Alcohol Organocatalyst.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9500
_journal_page_last               9511
_journal_paper_doi               10.1021/jo501433c
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H18 Br N O4'
_chemical_formula_sum            'C21 H18 Br N O4'
_chemical_formula_weight         428.27
_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                   9.7466(7)
_cell_length_b                   9.9284(7)
_cell_length_c                   18.7830(13)
_cell_measurement_reflns_used    4428
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      2.17
_cell_volume                     1817.6(2)
_computing_cell_refinement       'Bruker APEX2 (Bruker AXS, 2010)'
_computing_data_collection       'Bruker APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'Bruker SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'Brukre SHELXTL (Bruker AXS,2008)'
_computing_publication_material  'Bruker XCIF (Bruker AXS, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10503
_diffrn_reflns_theta_full        27.83
_diffrn_reflns_theta_max         27.83
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    2.289
_exptl_absorpt_correction_T_max  0.8941
_exptl_absorpt_correction_T_min  0.6210
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0051P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0601
_reflns_number_gt                3786
_reflns_number_total             4181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501433c_si_001.cif
_cod_data_source_block           p212121
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4030027--4030028.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               4030027