(Diacetoxy)iodobenzene-Mediated Oxidative C-H Amination of Imidazopyridines at Ambient Temperature.
Mondal, Susmita; Samanta, Sadhanendu; Jana, Sourav; Hajra, Alakananda; The Journal of organic chemistry 82 (2017) 4504–4510; doi:10.1021/acs.joc.7b00564

data_4032535
_publ_section_title
;
 (Diacetoxy)iodobenzene-Mediated Oxidative C-H Amination of
 Imidazopyridines at Ambient Temperature.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4504
_journal_page_last               4510
_journal_paper_doi               10.1021/acs.joc.7b00564
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C17 H17 N3 O'
_chemical_formula_weight         279.33
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                89.880(4)
_cell_angle_beta                 76.345(4)
_cell_angle_gamma                89.937(4)
_cell_formula_units_Z            8
_cell_length_a                   9.8883(7)
_cell_length_b                   16.9433(11)
_cell_length_c                   17.7267(12)
_cell_measurement_reflns_used    184
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.764
_cell_measurement_theta_min      1.421
_cell_volume                     2886.0(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  char
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.1018
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            94242
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.764
_diffrn_reflns_theta_min         1.421
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       vbchem219_0m_b
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 4950 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.3(10)
_refine_ls_extinction_coef       0.0183(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1514
_refine_ls_number_reflns         28907
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1948
_refine_ls_R_factor_gt           0.0910
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0879P)^2^+4.5550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2099
_refine_ls_wR_factor_ref         0.2778
_reflns_Friedel_coverage         0.991
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                14151
_reflns_number_total             28907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00564_si_002.cif
_cod_data_source_block           vbchem219_0m_b
_cod_database_code               4032535
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.984
_exptl_absorpt_special_details   SADABS
_shelx_res_checksum              46691
_shelx_hkl_checksum              32278