Highly enantioselective Michael addition reactions of 2-substituted benzofuran-3(2H)-ones to nitroolefins.
Zhang, Zhi-Pei; Dong, Nan; Li, Xin; Cheng, Jin-Pei; Organic & biomolecular chemistry 13 (2015) 9943–9947; doi:10.1039/c5ob01691f

data_7154685
_publ_section_title
;
 Highly enantioselective Michael addition reactions of 2-substituted
 benzofuran-3(2H)-ones to nitroolefins.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9943
_journal_page_last               9947
_journal_paper_doi               10.1039/c5ob01691f
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 Br N O4'
_chemical_formula_sum            'C18 H16 Br N O4'
_chemical_formula_weight         390.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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-2014/7
_audit_update_record
;
2015-07-07 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.729(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.528(3)
_cell_length_b                   7.509(2)
_cell_length_c                   11.706(4)
_cell_measurement_reflns_used    3353
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     825.5(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11465
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.754
_diffrn_reflns_theta_min         1.765
_exptl_absorpt_coefficient_mu    2.512
_exptl_absorpt_correction_T_max  0.668
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 1510 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.002(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4145
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.874
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0197
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0069P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0366
_refine_ls_wR_factor_ref         0.0368
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                3674
_reflns_number_total             4145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01691f2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 7154685.cif.'
_cod_database_code               7154685
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.608
_shelx_estimated_absorpt_t_max   0.689
_shelx_res_checksum              76392