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_4033099
_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            'C18 H26 O7'
_chemical_formula_weight         354.39
_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                 97.994(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.295(4)
_cell_length_b                   4.8587(6)
_cell_length_c                   13.2000(17)
_cell_measurement_reflns_used    830
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      18.28
_cell_measurement_theta_min      3.10
_cell_volume                     1797.1(4)
_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      200(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
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_diffrn_reflns_av_R_equivalents  0.0792
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_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6303
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.50
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_exptl_crystal_size_min          0.03
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
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_refine_ls_number_reflns         3156
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_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0716
_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^)+(0.0837P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1924
_reflns_number_gt                2029
_reflns_number_total             3156
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02178_si_002.cif
_cod_data_source_block           ic17074_compound_10
_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_cell_volume        1797.0(4)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4033099