NIS Mediated Cross-Coupling of C(sp<sup>2</sup>)-H and N-H Bonds: A Transition-Metal-Free Approach toward Indolo[1,2-a]quinazolinones.
Badigenchala, Sindhura; Sekar, Govindasamy; The Journal of organic chemistry 82 (2017) 7657–7665; doi:10.1021/acs.joc.7b01080

data_4037504
_publ_section_title
;
 NIS Mediated Cross-Coupling of C(sp<sup>2</sup>)-H and N-H Bonds: A
 Transition-Metal-Free Approach toward Indolo[1,2-a]quinazolinones.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7657
_journal_page_last               7665
_journal_paper_doi               10.1021/acs.joc.7b01080
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H11 Br N2 O '
_chemical_formula_sum            'C16 H11 Br N2 O'
_chemical_formula_weight         327.17
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.769(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0414(5)
_cell_length_b                   10.3635(8)
_cell_length_c                   15.9700(13)
_cell_measurement_reflns_used    2454
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.99
_cell_measurement_theta_min      2.36
_cell_volume                     1307.45(17)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.355
_exptl_absorpt_coefficient_mu    3.140
_exptl_absorpt_correction_T_max  0.372
_exptl_absorpt_correction_T_min  0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0294P)^2^+0.4249P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0717
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1734
_reflns_number_total             2313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01080_si_002.cif
_cod_data_source_block           715
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        ' C16 H11 Br N2 O '
_cod_database_code               4037504
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.192
_shelx_estimated_absorpt_t_max   0.372
_shelx_res_checksum              55161
_shelx_hkl_checksum              59907