Electrocatalytic Minisci Acylation Reaction of N-Heteroarenes Mediated by NH4I.
Wang, Qing-Qing; Xu, Kun; Jiang, Yang-Ye; Liu, Yong-Guo; Sun, Bao-Guo; Zeng, Cheng-Chu; Organic letters 19 (2017) 5517–5520; doi:10.1021/acs.orglett.7b02589

data_1547530
_publ_section_title
;
 Electrocatalytic Minisci Acylation Reaction of N-Heteroarenes Mediated by
 NH4I.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5517
_journal_page_last               5520
_journal_paper_doi               10.1021/acs.orglett.7b02589
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C10 H7 Br N2 O'
_chemical_formula_weight         251.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 113.318(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1898(2)
_cell_length_b                   19.2245(4)
_cell_length_c                   7.5937(2)
_cell_measurement_reflns_used    2486
_cell_measurement_temperature    293.02(10)
_cell_measurement_theta_max      73.7360
_cell_measurement_theta_min      4.5660
_cell_volume                     963.87(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.02(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3735
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.849
_diffrn_reflns_theta_min         4.600
_exptl_absorpt_coefficient_mu    5.542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.3050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1719
_reflns_number_total             1897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02589_si_002.cif
_cod_data_source_block           C
_cod_depositor_comments          'Adding full bibliography for 1547530.cif.'
_cod_database_code               1547530
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              30332
_shelx_hkl_checksum              6211