Efficient synthesis of α- and δ-carbolines by sequential Pd-catalyzed site-selective C-C and twofold C-N coupling reactions.
Hung, Tran Quang; Dang, Tuan Thanh; Janke, Julia; Villinger, Alexander; Langer, Peter; Organic & biomolecular chemistry 13 (2015) 1375–1386; doi:10.1039/c4ob02226b

data_7154204
_publ_section_title
;
 Efficient synthesis of \a- and \d-carbolines by sequential Pd-catalyzed
 site-selective C-C and twofold C-N coupling reactions.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1375
_journal_page_last               1386
_journal_paper_doi               10.1039/c4ob02226b
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C17 H11 F N2'
_chemical_formula_sum            'C17 H11 F N2'
_chemical_formula_weight         262.28
_chemical_name_systematic
;
5-(4-Fluorophenyl)-5<i>H</i>-pyrido[3,2-b]indole
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_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                 94.077(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.9224(7)
_cell_length_b                   11.0347(5)
_cell_length_c                   16.4227(9)
_cell_measurement_reflns_used    4771
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      60.482
_cell_measurement_theta_min      4.715
_cell_volume                     2516.6(2)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15409
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0421P)^2^+0.8289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                2167
_reflns_number_total             3322
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c4ob02226b2.cif
_cod_data_source_block           is_jj2h210
_cod_depositor_comments
'Adding full bibliography for 7154203--7154204.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7154204