Enantioselective Synthesis of Benzofuran-Fused N-Heterocycles via Chiral Squaramide Catalyzed [4 + 2] Cyclization of Azadienes with Azlactones.
Li, Xiaoping; Yan, Juzhang; Qin, Jialiang; Lin, Shilin; Chen, Weiwen; Zhan, Ruoting; Huang, Huicai; The Journal of organic chemistry 84 (2019) 8035–8045; doi:10.1021/acs.joc.9b00911

data_4037573
_publ_section_title
;
 Enantioselective Synthesis of Benzofuran-Fused N-Heterocycles via Chiral
 Squaramide Catalyzed [4 + 2] Cyclization of Azadienes with Azlactones.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8035
_journal_page_last               8045
_journal_paper_doi               10.1021/acs.joc.9b00911
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C38 H30 Br N2 O5.5 S'
_chemical_formula_weight         714.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                109.8940(10)
_cell_angle_beta                 97.0300(10)
_cell_angle_gamma                101.8830(10)
_cell_formula_units_Z            4
_cell_length_a                   10.04330(10)
_cell_length_b                   17.29000(10)
_cell_length_c                   20.81330(10)
_cell_measurement_reflns_used    25427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.6190
_cell_measurement_theta_min      4.2510
_cell_volume                     3252.13(5)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            37213
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        65.000
_diffrn_reflns_theta_max         65.000
_diffrn_reflns_theta_min         2.308
_exptl_absorpt_coefficient_mu    2.733
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             1468
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     861
_refine_ls_number_reflns         11044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0307P)^2^+2.2798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9626
_reflns_number_total             11044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00911_si_001.cif
_cod_data_source_block           XP01
_cod_depositor_comments
;

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C76 H60 Br2 N4 O11 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1429.22
_cod_database_code               4037573
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              88637
_shelx_hkl_checksum              62069