Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives.
Yang, Shu-Mei; Madhusudhan Reddy, Ganapuram; Liu, Meng-Hsien; Wang, Tzu-Ping; Yu, Jhen-Kuei; Lin, Wenwei; The Journal of organic chemistry 82 (2017) 781–789; doi:10.1021/acs.joc.6b02526

data_4032217
_publ_section_title
;
 Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an
 Unexpected \a-Addition of \a,\b-Unsaturated \g-Butyrolactams to Coumarin
 Derivatives.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              781
_journal_page_last               789
_journal_paper_doi               10.1021/acs.joc.6b02526
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C21 H15 Br O5'
_chemical_formula_sum            'C21 H15 Br O5'
_chemical_formula_weight         427.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.738(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0753(9)
_cell_length_b                   24.060(3)
_cell_length_c                   9.5701(10)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1846.5(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0932
_diffrn_reflns_av_sigmaI/netI    0.0992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            13462
_diffrn_reflns_theta_full        25.16
_diffrn_reflns_theta_max         25.16
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    2.256
_exptl_absorpt_correction_T_max  0.8059
_exptl_absorpt_correction_T_min  0.6024
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0986P)^2^+0.8476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.2097
_reflns_number_gt                1869
_reflns_number_total             3304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02526_si_004.cif
_cod_data_source_block           ch16033
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4032217