FeCl3-Promoted Annulation of 2-haloindoles: Switchable Synthesis of Spirooxindole-chromeno[2,3-b]indoles and Spirooxindole-chromeno[3,2-b]indoles.
Luo, Mupeng; Zhu, Xinlei; Liu, Rufeng; Yu, Shunming; Wei, Wanguo; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03300

data_4037952
_publ_section_title
;
 FeCl3-Promoted Annulation of 2-haloindoles: Switchable Synthesis of
 Spirooxindole-chromeno[2,3-b]indoles and
 Spirooxindole-chromeno[3,2-b]indoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03300
_journal_year                    2020
_chemical_formula_moiety         'C24 H16 Cl F N2 O4 S'
_chemical_formula_sum            'C24 H16 Cl F N2 O4 S'
_chemical_formula_weight         482.90
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/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                 126.62(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.1173(4)
_cell_length_b                   20.3155(5)
_cell_length_c                   13.0813(3)
_cell_measurement_reflns_used    8014
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.65
_cell_measurement_theta_min      3.61
_cell_volume                     4077.6(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9574
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         66.50
_diffrn_reflns_theta_min         3.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.029
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.4606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.00079(6)
_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   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0405P)^2^+4.3278P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                3297
_reflns_number_total             3396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b03300_si_005.cif
_cod_data_source_block           480
_cod_original_cell_volume        4077.75(16)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4037952