A new synthetic approach to fused nine-ring systems of the indolo[3,2-b]carbazole family through double Pd-catalyzed intramolecular C‒H arylation
Irgashev, Roman A.; Kazin, Nikita A.; Kim, Grigory A.; Rusinov, Gennady L.; Charushin, Valery N.; RSC Adv. 6 (2016) 70106–; doi:10.1039/C6RA11796A

data_7226019
_publ_section_title
;
 A new synthetic approach to fused nine-ring systems of the
 indolo[3,2-b]carbazole family through double Pd-catalyzed intramolecular
 C--H arylation
;
_journal_issue                   74
_journal_name_full               'RSC Adv.'
_journal_page_first              70106
_journal_paper_doi               10.1039/C6RA11796A
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         '2(C28 H24 N O)'
_chemical_formula_sum            'C56 H48 N2 O2'
_chemical_formula_weight         780.96
_chemical_name_systematic
6,15-Dihexyl-7,16-diphenyl-6,15-dihydroindeno[1,2-b]indeno[2',1':5,6]indolo[2,3-h]carbazole-9,18-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2015-09-14
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2016-05-05 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.188(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9788(8)
_cell_length_b                   25.286(3)
_cell_length_c                   16.0994(7)
_cell_measurement_reflns_used    2454
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      21.4440
_cell_measurement_theta_min      2.5830
_cell_volume                     4398.9(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9985
_diffrn_measurement_details
;
  1 omega  -20.00   21.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.1050  -99.0000   60.0000 41

  2 omega  -25.00   65.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4490  -99.0000 -120.0000 90

  3 omega  -18.00   95.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4490    0.0000 -150.0000 113
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0137823000
_diffrn_orient_matrix_UB_12      -0.0271017000
_diffrn_orient_matrix_UB_13      -0.0049715000
_diffrn_orient_matrix_UB_21      0.0403669000
_diffrn_orient_matrix_UB_22      0.0003256000
_diffrn_orient_matrix_UB_23      0.0395925000
_diffrn_orient_matrix_UB_31      -0.0498647000
_diffrn_orient_matrix_UB_32      -0.0072736000
_diffrn_orient_matrix_UB_33      0.0202731000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19797
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.06
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1656
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     642
_refine_ls_number_reflns         8977
_refine_ls_number_restraints     142
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1733
_refine_ls_R_factor_gt           0.0680
_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^)+(0.0950P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.2204
_reflns_number_gt                3820
_reflns_number_total             8977
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra11796a2.cif
_cod_data_source_block           exp_664
_cod_database_code               7226019
_reflns_odcompleteness_completeness 82.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_solvent_exptl_crystal_recrystallization_method chloroform