Stereoselective synthesis of pyridinones: application to the synthesis of (-)-barrenazines.
Focken, Thilo; Charette, André B; Organic letters 8 (2006) 2985–2988; doi:10.1021/ol0609006

data_1506029
_publ_section_title
;
 Stereoselective synthesis of pyridinones: application to the synthesis of
 (-)-barrenazines.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2985
_journal_page_last               2988
_journal_paper_doi               10.1021/ol0609006
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C20 H27 I N2 O2'
_chemical_formula_sum            'C20 H27 I N2 O2'
_chemical_formula_weight         454.34
_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                 90.87(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.051(3)
_cell_length_b                   8.794(2)
_cell_length_c                   25.949(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      15.00
_cell_volume                     2065.2(11)
_computing_cell_refinement       'CAD4 Program (Nonius 1989)'
_computing_data_collection       'CAD4 Program (Nonius 1989)'
_computing_data_reduction        'Local Program'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  Enraf-Nonius-CAD4
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20013
_diffrn_reflns_theta_full        69.94
_diffrn_reflns_theta_max         69.94
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        1.60
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    12.293
_exptl_absorpt_correction_T_max  0.3000
_exptl_absorpt_correction_T_min  0.0700
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'Gaussian from crystal shape'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_refine_diff_density_max         2.948
_refine_diff_density_min         -1.544
_refine_diff_density_rms         0.194
_refine_ls_abs_structure_details 'Flack H D (1983), 3563 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.003(9)
_refine_ls_extinction_coef       0.00188(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   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         7740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0913P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                6138
_reflns_number_total             7740
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol0609006si20060523_050840.cif
_cod_data_source_block           cha118
_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.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (52
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (70 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1506029