Synthesis of indolo[1,2-f]phenanthridines by Pd-catalyzed domino C-N coupling/hydroamination/C-H arylation reactions.
Ngo, Thang Ngoc; Ehlers, Peter; Dang, Tuan Thanh; Villinger, Alexander; Langer, Peter; Organic & biomolecular chemistry 13 (2015) 3321–3330; doi:10.1039/c5ob00013k

data_7154317
_publ_section_title
;
 Synthesis of indolo[1,2-f]phenanthridines by Pd-catalyzed domino C-N
 coupling/hydroamination/C-H arylation reactions.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3321
_journal_page_last               3330
_journal_paper_doi               10.1039/c5ob00013k
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C21 H14 F N'
_chemical_formula_sum            'C21 H14 F N'
_chemical_formula_weight         299.33
_chemical_name_systematic
;
3-Fluoro-6-methylindolo[1,2-<i>f</i>]phenanthridine
;
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-01-05 deposited with the CCDC.
2015-01-28 downloaded from the CCDC.
;
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_cell_measurement_theta_min      2.81
_cell_volume                     1440.99(17)
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_diffrn_ambient_temperature      173(2)
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_diffrn_measured_fraction_theta_max 0.999
_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
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_diffrn_reflns_limit_l_min       -9
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_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            colourless
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_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.7543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1292
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_reflns_number_gt                2993
_reflns_number_total             3832
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00013k2.cif
_cod_data_source_block           is_indolo_d2
_cod_depositor_comments          'Adding full bibliography for 7154317.cif.'
_cod_database_code               7154317
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
_shelx_res_checksum              23292