Facile construction of pyrrolo[1,2-b]isoquinolin-10(5H)-ones via a redox-amination-aromatization-Friedel-Crafts acylation cascade reaction and discovery of novel topoisomerase inhibitors.
Wu, Shanchao; Liu, Na; Dong, Guoqiang; Ma, Lin; Wang, Shengzheng; Shi, Wencai; Fang, Kun; Chen, Shuqiang; Li, Jian; Zhang, Wannian; Sheng, Chunquan; Wang, Wei; Chemical communications (Cambridge, England) 52 (2016) 9593–9596; doi:10.1039/c6cc03071h

data_7124646
_publ_section_title
;
 Facile construction of pyrrolo[1,2-b]isoquinolin-10(5H)-ones via a
 redox-amination-aromatization-Friedel-Crafts acylation cascade reaction
 and discovery of novel topoisomerase inhibitors.
;
_journal_issue                   61
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9593
_journal_page_last               9596
_journal_paper_doi               10.1039/c6cc03071h
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C18 H13 N O'
_chemical_formula_weight         259.29
_chemical_name_common            'compound 3j'
_chemical_name_systematic        6-phenylpyrrolo[1,2-b]isoquinolin-10(5H)-one
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-03-14 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.662(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.016(4)
_cell_length_b                   9.223(3)
_cell_length_c                   13.978(5)
_cell_measurement_reflns_used    803
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.616
_cell_measurement_theta_min      2.648
_cell_volume                     1287.0(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5708
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.040
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0710P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1681
_reflns_number_total             2525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc03071h2.cif
_cod_data_source_block           a51209b
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7124646
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-2
_shelx_res_checksum              48876
_shelx_hkl_checksum              33020