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_7119444
_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            'C26 H18 F2 N2 O4'
_chemical_formula_weight         460.42
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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
_audit_update_record
;
2015-06-29 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                78.111(2)
_cell_angle_beta                 79.431(2)
_cell_angle_gamma                87.801(2)
_cell_formula_units_Z            2
_cell_length_a                   6.0426(10)
_cell_length_b                   12.222(2)
_cell_length_c                   15.374(3)
_cell_measurement_reflns_used    1302
_cell_measurement_temperature    298(2)
_cell_volume                     1092.2(3)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8750
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9506
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0862P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1826
_reflns_number_gt                1885
_reflns_number_total             3897
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc02659a2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7119444