Enantioselective organocatalytic domino Michael-acetalization-Henry reactions of 2-hydroxynitrostyrene and aldehyde for the synthesis of tetrahydro-6H-benzo[c]chromenones.
Hong, Bor-Cherng; Kotame, Prakash; Liao, Ju-Hsiou; Organic & biomolecular chemistry 9 (2011) 382–386; doi:10.1039/C0OB00834F

data_7151709
_publ_section_title
;
 Enantioselective organocatalytic domino Michael-acetalization-Henry
 reactions of 2-hydroxynitrostyrene and aldehyde for the synthesis of
 tetrahydro-6H-benzo[c]chromenones.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              382
_journal_page_last               386
_journal_paper_doi               10.1039/C0OB00834F
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H12 Br N O4'
_chemical_formula_sum            'C12 H12 Br N O4'
_chemical_formula_weight         314.14
_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                   6.8992(8)
_cell_length_b                   6.9979(8)
_cell_length_c                   24.978(3)
_cell_measurement_reflns_used    526
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.529
_cell_measurement_theta_min      -23.529
_cell_volume                     1205.9(2)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    Ortep-3
_computing_publication_material  'Wingx publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       'phi-omega scan'
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13963
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.415
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9929
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunky
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.243
_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   0.006(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0250
_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^)+(0.0235P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0492
_refine_ls_wR_factor_ref         0.0500
_reflns_number_gt                2621
_reflns_number_total             2924
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00834F.TXT
_cod_data_source_block           pmk02364
_cod_depositor_comments
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The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Empirical' changed to 'empirical'
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_enum 1555 2011-01-17 13:19:09Z saulius 
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_cod_database_code               7151709