Metal-Free Regioselective Hypervalent Iodine-Mediated C-2 and C-3 Difunctionalization of N-Substituted Indoles.
Xu, Dongdong; Sun, Wen-Wu; Xie, Yanli; Liu, Ji-Kai; Liu, Bin; Zhou, Yingbi; Wu, Bin; The Journal of organic chemistry 81 (2016) 11081–11094; doi:10.1021/acs.joc.6b02078

data_4037379
_publ_section_title
;
 Metal-Free Regioselective Hypervalent Iodine-Mediated C-2 and C-3
 Difunctionalization of N-Substituted Indoles.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11081
_journal_page_last               11094
_journal_paper_doi               10.1021/acs.joc.6b02078
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C12 H6 Cl3 N3 O'
_chemical_formula_sum            'C12 H6 Cl3 N3 O'
_chemical_formula_weight         314.55
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.3740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7940(11)
_cell_length_b                   8.4331(7)
_cell_length_c                   12.0362(10)
_cell_measurement_reflns_used    9766
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.82
_cell_measurement_theta_min      2.57
_cell_volume                     1277.39(19)
_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 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.938
_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  0.0191
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13702
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.924
_diffrn_reflns_theta_min         1.618
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.300
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.6476
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0370P)^2^+0.5860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0746
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3546
_reflns_number_total             3787
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02078_si_003.cif
_cod_data_source_block           mo_bwxdd71_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037379
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.648
_shelx_estimated_absorpt_t_max   0.815
_shelx_res_checksum              30205
_shelx_hkl_checksum              55535