Annulation Reaction of 3-Acylmethylidene Oxindoles with Huisgen Zwitterions and Its Applications in the Syntheses of Pyrrolo[4,3,2-de]quinolinones and Marine Alkaloids Ammosamides.
Yang, Changjiang; Chen, Xiangyu; Tang, Tong; He, Zhengjie; Organic letters 18 (2016) 1486–1489; doi:10.1021/acs.orglett.6b00456

data_1542626
_publ_section_title
;
 Annulation Reaction of 3-Acylmethylidene Oxindoles with Huisgen
 Zwitterions and Its Applications in the Syntheses of
 Pyrrolo[4,3,2-de]quinolinones and Marine Alkaloids Ammosamides.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1486
_journal_page_last               1489
_journal_paper_doi               10.1021/acs.orglett.6b00456
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C29 H27 N3 O5'
_chemical_formula_sum            'C29 H27 N3 O5'
_chemical_formula_weight         497.54
_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                 91.481(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4022(9)
_cell_length_b                   10.9390(6)
_cell_length_c                   16.5069(11)
_cell_measurement_reflns_used    5539
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.23
_cell_volume                     2419.2(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23506
_diffrn_reflns_theta_full        28.12
_diffrn_reflns_theta_max         28.12
_diffrn_reflns_theta_min         1.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0149(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0729P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1348
_reflns_number_gt                4626
_reflns_number_total             5839
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00456_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 1542621--1542626.cif.'
_cod_database_code               1542626