Controllable Synthesis of Pyrido[2,3-b]indol-4-ones or Indolo[3,2-b]quinolines via Formal Intramolecular C(sp2)-H Functionalization
Song, Bo; Wang, Mengdan; Xu, Murong; Kong, Lingkai; Xie, Huihui; Wang, Cheng-Yu; LI, Yanzhong; Organic & Biomolecular Chemistry  (2019) –; doi:10.1039/C9OB02108F

data_7157194
_publ_section_title
;
 Controllable Synthesis of Pyrido[2,3-b]indol-4-ones or
 Indolo[3,2-b]quinolines via Formal Intramolecular C(sp2)-H
 Functionalization
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB02108F
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24.5 H18 Br Cl N2 O'
_chemical_formula_weight         471.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-07-29 deposited with the CCDC.	2019-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.0281(10)
_cell_length_b                   11.0265(3)
_cell_length_c                   12.8199(4)
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.876
_cell_measurement_theta_min      5.071
_cell_volume                     4103.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37638
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.535
_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.375
_refine_diff_density_min         -1.337
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
; 
 Flack x determined using 3066 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.018(4)
_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   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         8004
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0194P)^2^+4.2472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                7183
_reflns_number_total             8004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02108f2.cif
_cod_data_source_block           d8v18015
_cod_original_formula_sum        'C24.50 H18 Br Cl N2 O'
_cod_database_code               7157194
_shelx_estimated_absorpt_t_min   0.698
_shelx_estimated_absorpt_t_max   0.782
_shelxl_version_number           2013-4
_shelx_res_checksum              14357