Insights into the unexpected chemoselectivity in Brønsted acid catalyzed cyclization of isatins with enaminones: convenient synthesis of pyrrolo[3,4-c]quinolin-1-ones and spirooxindoles
Xu, Hui; Zhou, Bei; Zhou, Pan; Zhou, Jie; Shen, Yuehai; Yu, Fu-Chao; Lu, Ling-Ling; Chemical Communications (Cambridge, United Kingdom) 52 (2016) 8002–8005; doi:10.1039/c6cc02659a

data_7119445
_publ_section_title
;
 Insights into the unexpected chemoselectivity in Br\/onsted acid catalyzed
 cyclization of isatins with enaminones: convenient synthesis of
 pyrrolo[3,4-c]quinolin-1-ones and spirooxindoles
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   51
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              8002
_journal_page_last               8005
_journal_paper_doi               10.1039/c6cc02659a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C31 H21 F N4 O4'
_chemical_formula_weight         532.52
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-13 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.660(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.522(3)
_cell_length_b                   19.035(8)
_cell_length_c                   20.250(8)
_cell_measurement_reflns_used    882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.57
_cell_measurement_theta_min      2.36
_cell_volume                     2511.3(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0730
_diffrn_reflns_av_sigmaI/netI    0.1088
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9923
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9705
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(15)
_refine_ls_extinction_coef       0.0052(5)
_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   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4444
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0440P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                2431
_reflns_number_total             4444
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc02659a2.cif
_cod_data_source_block           1a
_cod_original_cell_volume        2511.2(17)
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7119445