Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic Centers and an Approach to Aflatoxin Analogues.
Hsieh, Yu-You; Raja, Arun; Hong, Bor-Cherng; Kotame, Prakash; Chang, Wan-Chen; Lee, Gene-Hsiang; The Journal of organic chemistry 82 (2017) 12840–12848; doi:10.1021/acs.joc.7b02178

data_4033097
_publ_section_title
;
 Organocatalytic Enantioselective Michael-Acetalization-Henry Reaction
 Cascade of 2-Hydroxynitrostyrene and 5-Oxohexanal for the Entry to the
 Hexahydro-6H-benzo[c]chromenones with Four Consecutive Stereogenic
 Centers and an Approach to Aflatoxin Analogues.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12840
_journal_page_last               12848
_journal_paper_doi               10.1021/acs.joc.7b02178
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H14 Br N O5'
_chemical_formula_weight         356.17
_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                 115.7253(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9789(7)
_cell_length_b                   7.0934(5)
_cell_length_c                   11.0379(7)
_cell_measurement_reflns_used    3655
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.90
_cell_measurement_theta_min      2.27
_cell_volume                     703.87(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       '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  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11543
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    2.941
_exptl_absorpt_correction_T_max  0.8433
_exptl_absorpt_correction_T_min  0.3210
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.986
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3219
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.4283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                3012
_reflns_number_total             3219
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02178_si_002.cif
_cod_data_source_block           ic15687_compound_4b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033097--4033099.cif.
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4033097