Enantioselective synthesis of benzofurans and benzoxazines via an olefin cross-metathesis-intramolecular oxo-Michael reaction
Jun-Wei Zhang; Quan Cai; Qing Gu; Xiao-Xin Shi; Shu-Li You; Chem.Commun. 49 (2013) 7750–; doi:10.1039/c3cc43937b

data_7109658
_publ_section_title
;
 Enantioselective synthesis of benzofurans and benzoxazines via an olefin
 cross-metathesis-intramolecular oxo-Michael reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              7750
_journal_paper_doi               10.1039/c3cc43937b
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H13 Br O2'
_chemical_formula_weight         317.17
_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                   7.2969(11)
_cell_length_b                   11.1694(16)
_cell_length_c                   16.483(2)
_cell_measurement_reflns_used    1605
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.679
_cell_measurement_theta_min      4.405
_cell_volume                     1343.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7736
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    3.054
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51956
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.026(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2627
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0643P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                1955
_reflns_number_total             2627
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc43937b.txt
_cod_data_source_block           cd21218
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7109658