Asymmetric Michael addition reactions of 3-substituted benzofuran-2(3H)-ones to nitroolefins catalyzed by a bifunctional tertiary-amine thiourea.
Li, Xin; Xue, Xiao-Song; Liu, Cong; Wang, Bin; Tan, Bo-Xuan; Jin, Jia-Lu; Zhang, Yue-Yan; Dong, Nan; Cheng, Jin-Pei; Organic & biomolecular chemistry 10 (2012) 413–420; doi:10.1039/c1ob06518a

data_7152155
_publ_section_title
;
 Asymmetric Michael addition reactions of 3-substituted
 benzofuran-2(3H)-ones to nitroolefins catalyzed by a bifunctional
 tertiary-amine thiourea.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              413
_journal_page_last               420
_journal_paper_doi               10.1039/c1ob06518a
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C17 H14 Cl N O4'
_chemical_formula_sum            'C17 H14 Cl N O4'
_chemical_formula_weight         331.74
_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                 93.356(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2170(14)
_cell_length_b                   7.4840(8)
_cell_length_c                   14.4870(15)
_cell_measurement_reflns_used    5192
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.00
_cell_volume                     1538.8(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0848
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17795
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.43
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.9533
_exptl_absorpt_correction_T_min  0.9433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         7202
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0274P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0837
_reflns_number_gt                5649
_reflns_number_total             7202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06518a.txt
_cod_data_source_block           shelxl
_cod_database_code               7152155