One-Pot Enantioselective Synthesis of Functionalized Pyranocoumarins and 2-Amino-4H-chromenes: Discovery of a Type of Potent Antibacterial Agent
Gen Zhang; Yaohu Zhang; Jiexi Yan; Ru Chen; Shoulei Wang; Yunxia Ma; Rui Wang; Journal of Organic Chemistry 77 (2012) 878–888; doi:10.1021/jo202020m

data_4026884
_publ_section_title
;
 One-Pot Enantioselective Synthesis of Functionalized Pyranocoumarins and
 2-Amino-4H-chromenes: Discovery of a Type of Potent Antibacterial Agent
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              878
_journal_page_last               888
_journal_paper_doi               10.1021/jo202020m
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C19 H11 Br N2 O3'
_chemical_formula_weight         395.21
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.247(18)
_cell_angle_beta                 105.854(18)
_cell_angle_gamma                97.890(18)
_cell_formula_units_Z            2
_cell_length_a                   8.009(14)
_cell_length_b                   11.045(19)
_cell_length_c                   11.59(2)
_cell_measurement_reflns_used    1371
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.41
_cell_measurement_theta_min      2.75
_cell_volume                     871(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0701
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5936
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    2.379
_exptl_absorpt_correction_T_max  0.5877
_exptl_absorpt_correction_T_min  0.5165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0412P)^2^+0.1778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                1867
_reflns_number_total             3168
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202020m_si_003.cif
_cod_data_source_block           p-1
_cod_database_code               4026884