Novel synthesis of 5-methyl-5,10-dihydroindolo[3,2-b]indoles by Pd-catalyzed C-C and two-fold C-N coupling reactions.
Hung, Tran Quang; Hancker, Sören; Villinger, Alexander; Lochbrunner, Stefan; Dang, Tuan Thanh; Friedrich, Aleksej; Breitsprecher, Wolfgang; Langer, Peter; Organic & biomolecular chemistry 13 (2015) 583–591; doi:10.1039/c4ob01723d

data_7154357
_publ_section_title
;
 Novel synthesis of 5-methyl-5,10-dihydroindolo[3,2-b]indoles by
 Pd-catalyzed C-C and two-fold C-N coupling reactions.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              583
_journal_page_last               591
_journal_paper_doi               10.1039/c4ob01723d
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C25 H24 N2'
_chemical_formula_sum            'C25 H24 N2'
_chemical_formula_weight         352.46
_chemical_name_systematic
;
5-(4-(<i>tert</i>-Butyl)phenyl)-10-methyl-5,10-dihydroindolo[3,2-b]indole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 103.811(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8957(3)
_cell_length_b                   23.4982(7)
_cell_length_c                   8.5844(3)
_cell_measurement_reflns_used    4520
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      59.975
_cell_measurement_theta_min      5.477
_cell_volume                     1938.43(11)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-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  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27546
_diffrn_reflns_theta_full        30.08
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5629
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0536P)^2^+0.3631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                3510
_reflns_number_total             5629
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c4ob01723d2.cif
_cod_data_source_block           is_1h003
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7154357