Regioselective ring expansion followed by H-shift of 3-ylidene oxindoles: a convenient synthesis of N-substituted/un-substituted pyrrolo[2,3-c] quinolines and marinoquinolines
Ramu, Gopathi; Ambala, Srinivas; Nanubolu, Jagadeesh Babu; Nagendra Babu, Bathini; RSC Advances 9 (2019) 35068–; doi:10.1039/C9RA07831B

data_7234882
_publ_section_title
;
 Regioselective ring expansion followed by H-shift of 3-ylidene oxindoles:
 a convenient synthesis of N-substituted/un-substituted pyrrolo[2,3-c]
 quinolines and marinoquinolines
;
_journal_issue                   60
_journal_name_full               'RSC Advances'
_journal_page_first              35068
_journal_paper_doi               10.1039/C9RA07831B
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C15 H14 N2 O3'
_chemical_formula_sum            'C15 H14 N2 O3'
_chemical_formula_weight         270.28
_chemical_name_systematic
'ethyl 5-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-03-20 deposited with the CCDC.    2019-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                96.04(3)
_cell_angle_beta                 90.884(19)
_cell_angle_gamma                90.83(2)
_cell_formula_units_Z            2
_cell_length_a                   6.063(4)
_cell_length_b                   9.023(7)
_cell_length_c                   11.915(8)
_cell_measurement_reflns_used    5552
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.702
_cell_volume                     648.0(8)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8651
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         2.270
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       Needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.12(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1084P)^2^+0.0437P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2053
_reflns_number_total             2526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra07831b2.cif
_cod_data_source_block           KA279_0m
_cod_original_cell_volume        648.1(8)
_cod_database_code               7234882
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              18643