Metal-free C(sp<sup>2</sup>)-H functionalization of azoles: K<sub>2</sub>CO<sub>3</sub>/I<sub>2</sub>-mediated oxidation, imination, and amination.
Das, Ranajit; Banerjee, Mainak; Rai, Rakesh Kumar; Karri, Ramesh; Roy, Gouriprasanna; Organic & biomolecular chemistry 16 (2018) 4243–4260; doi:10.1039/c8ob00535d

data_7156183
_publ_section_title
;
 Metal-free C(sp<sup>2</sup>)-H functionalization of azoles:
 K<sub>2</sub>CO<sub>3</sub>/I<sub>2</sub>-mediated oxidation, imination,
 and amination.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4243
_journal_page_last               4260
_journal_paper_doi               10.1039/c8ob00535d
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C10 H9 I N2'
_chemical_formula_weight         285.10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-03 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   13.1444(5)
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_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.34
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_cell_volume                     1047.24(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Photon area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22060
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         2.797
_exptl_absorpt_coefficient_mu    3.014
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_description       Cubic
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.184
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 864 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(8)
_refine_ls_extinction_coef       0.0290(9)
_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   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0132
_refine_ls_R_factor_gt           0.0126
_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^)+(0.0144P)^2^+0.1759P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0294
_refine_ls_wR_factor_ref         0.0296
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2101
_reflns_number_total             2146
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00535d2.cif
_cod_data_source_block           BnImI_b
_cod_depositor_comments
'Adding full bibliography for 7156181--7156186.cif.'
_cod_database_code               7156183
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.492
_shelx_estimated_absorpt_t_max   0.607
_shelx_res_checksum              60837