Vilsmeier-Haack reaction of 7-acetyl-2-arylindoles: a convenient method for the synthesis of 6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-1,5-dicarbaldehydes.
Mphahlele, Malose J.; Mmonwa, Mmakwena M.; Organic & biomolecular chemistry 17 (2019) 2204–2211; doi:10.1039/c8ob03040e

data_7156663
_publ_section_title
;
 Vilsmeier-Haack reaction of 7-acetyl-2-arylindoles: a convenient method
 for the synthesis of
 6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-1,5-dicarbaldehydes.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2204
_journal_page_last               2211
_journal_paper_doi               10.1039/c8ob03040e
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C19 H9 Br F N O3'
_chemical_formula_weight         398.18
_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-2017/1
_audit_update_record
;
2018-11-28 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.358(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3505(4)
_cell_length_b                   15.9493(9)
_cell_length_c                   13.0154(8)
_cell_measurement_temperature    173(2)
_cell_volume                     1519.20(15)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            43490
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         21.989
_diffrn_reflns_theta_min         2.015
_exptl_absorpt_coefficient_mu    1.472
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             792
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0287P)^2^+1.7226P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0810
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2951
_reflns_number_total             3787
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob03040e2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7156663.cif.'
_cod_database_code               7156663
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              20827