One-Pot Access to Indolo[2,3-b]quinolines by Electrophile-Triggered Cross-Amination/Friedel-Crafts Alkylation of Indoles with 1-(2-Tosylaminophenyl)ketones
Shaukat Ali; Ying-Xiu Li; Saeed Anwar; Fang Yang; Zi-Sheng Chen; Yong-Min Liang; Journal of Organic Chemistry 77 (2012) 424–431; doi:10.1021/jo202035p

data_4026856
_publ_section_title
;
 One-Pot Access to Indolo[2,3-b]quinolines by Electrophile-Triggered
 Cross-Amination/Friedel-Crafts Alkylation of Indoles with
 1-(2-Tosylaminophenyl)ketones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              424
_journal_page_last               431
_journal_paper_doi               10.1021/jo202035p
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C22 H15 Cl N2'
_chemical_formula_weight         342.81
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.847(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.668(10)
_cell_length_b                   7.081(7)
_cell_length_c                   22.36(2)
_cell_measurement_reflns_used    1179
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.63
_cell_measurement_theta_min      3.02
_cell_volume                     1685(3)
_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 0.971
_diffrn_measured_fraction_theta_max 0.971
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_sigmaI/netI    0.1064
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6348
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_correction_T_min  0.9442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0783
_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^)+(0.0644P)^2^+2.0119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1925
_refine_ls_wR_factor_ref         0.2213
_reflns_number_gt                1783
_reflns_number_total             3016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202035p_si_002.cif
_cod_data_source_block           p21n
_cod_database_code               4026856