Halogen Bond-Assisted Electron-Catalyzed Atom Economic Iodination of Heteroarenes at Room Temperature.
Kazi, Imran; Guha, Somraj; Sekar, Govindasamy; The Journal of organic chemistry 84 (2019) 6642–6654; doi:10.1021/acs.joc.9b00174

data_4034616
_publ_section_title
;
 Halogen Bond-Assisted Electron-Catalyzed Atom Economic Iodination of
 Heteroarenes at Room Temperature.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6642
_journal_page_last               6654
_journal_paper_doi               10.1021/acs.joc.9b00174
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C9 H7 I N2'
_chemical_formula_sum            'C9 H7 I N2'
_chemical_formula_weight         270.07
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.247(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9093(4)
_cell_length_b                   4.20460(10)
_cell_length_c                   17.3663(6)
_cell_measurement_reflns_used    3642
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.35
_cell_volume                     868.93(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0212
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6760
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.968
_diffrn_reflns_theta_max         24.968
_diffrn_reflns_theta_min         2.347
_exptl_absorpt_coefficient_mu    3.626
_exptl_absorpt_correction_T_max  0.713
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.064
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0202
_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^)+(0.0165P)^2^+0.8924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0423
_refine_ls_wR_factor_ref         0.0442
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1303
_reflns_number_total             1514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00174_si_002.cif
_cod_data_source_block           2i
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034616
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.503
_shelx_estimated_absorpt_t_max   0.713
_shelx_res_checksum              87495
_shelx_hkl_checksum              77896