Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives.
Chang, Geng-Hua; Wang, Chein-Yi; Madhusudhan Reddy, G.; Tsai, Yi-Ling; Lin, Wenwei; The Journal of organic chemistry 81 (2016) 10071–10080; doi:10.1021/acs.joc.6b02041

data_4037351
_publ_section_title
;
 Enantioselective Synthesis of Polysubstituted
 Benzopyrano[3,4-c]pyrrolidine Frameworks via [3 + 2] Cycloaddition of
 Azomethine Ylides and Coumarin Derivatives.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10071
_journal_page_last               10080
_journal_paper_doi               10.1021/acs.joc.6b02041
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C29 H23 Br2 Cl2 N O7 S'
_chemical_formula_sum            'C29 H23 Br2 Cl2 N O7 S'
_chemical_formula_weight         760.26
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                94.018(14)
_cell_angle_beta                 106.912(14)
_cell_angle_gamma                109.068(14)
_cell_formula_units_Z            2
_cell_length_a                   9.561(7)
_cell_length_b                   11.973(8)
_cell_length_c                   14.769(9)
_cell_measurement_reflns_used    3287
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.22
_cell_measurement_theta_min      2.41
_cell_volume                     1503.1(18)
_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 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX2'
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12519
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    2.992
_exptl_absorpt_correction_T_max  0.9156
_exptl_absorpt_correction_T_min  0.6971
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+1.8395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                3814
_reflns_number_total             5289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02041_si_002.cif
_cod_data_source_block           ch17825
_cod_original_cell_volume        1503.1(17)
_cod_database_code               4037351