Catalytic enantioselective Michael addition of 2-substituted benzofuran-3-ones to 2-enoyl pyridines.
Sivamuthuraman, Koilpitchai; Kesavan, Venkitasamy; Organic & biomolecular chemistry 17 (2019) 7166–7171; doi:10.1039/c9ob01069f

data_7156968
_publ_section_title
;
 Catalytic enantioselective Michael addition of 2-substituted
 benzofuran-3-ones to 2-enoyl pyridines.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7166
_journal_page_last               7171
_journal_paper_doi               10.1039/c9ob01069f
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H21 N O6'
_chemical_formula_sum            'C25 H21 N O6'
_chemical_formula_weight         431.43
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-10-16 deposited with the CCDC.    2019-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                100.671(2)
_cell_angle_beta                 93.538(2)
_cell_angle_gamma                93.953(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2333(3)
_cell_length_b                   11.1033(4)
_cell_length_c                   11.1547(3)
_cell_measurement_reflns_used    9440
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.51
_cell_measurement_theta_min      2.21
_cell_volume                     1117.89(6)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f 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  0.0254
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21852
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.217
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 2295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(3)
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         7849
_refine_ls_number_restraints     110
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0563P)^2^+0.1379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5587
_reflns_number_total             7849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01069f2.cif
_cod_data_source_block           5OME
_cod_depositor_comments          'Adding full bibliography for 7156968.cif.'
_cod_database_code               7156968
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              65897