TEMPO-Mediated C-H Amination of Benzoxazoles with N-Heterocycles.
Wang, Jian; Li, Jiang-Hua; Guo, Yidong; Dong, Hongbo; Liu, Qiang; Yu, Xiao-Qi; The Journal of organic chemistry 85 (2020) 12797–12803; doi:10.1021/acs.joc.0c01921

data_4038792
_publ_section_title
;
 TEMPO-Mediated C-H Amination of Benzoxazoles with N-Heterocycles.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12797
_journal_page_last               12803
_journal_paper_doi               10.1021/acs.joc.0c01921
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C11 H9 N3 O'
_chemical_formula_sum            'C11 H9 N3 O'
_chemical_formula_weight         199.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                86.895(7)
_cell_angle_beta                 81.037(8)
_cell_angle_gamma                71.308(8)
_cell_formula_units_Z            2
_cell_length_a                   7.0730(7)
_cell_length_b                   8.1167(7)
_cell_length_c                   8.7016(9)
_cell_measurement_reflns_used    2252
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      71.6970
_cell_measurement_theta_min      6.6900
_cell_volume                     467.42(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -63.00  32.00   1.00    1.00    --  -36.04  77.00  60.00   95
  2  \w   -104.00  -9.00   1.00    1.00    --  -36.04 -77.00 -60.00   95
  3  \w    -35.00  65.00   1.00    1.00    --   36.04 -19.00 120.00  100
  4  \w      1.00  75.00   1.00    1.00    --   36.04 -99.00 120.00   74
  5  \w     23.00  89.00   1.00    1.00    --   36.04-125.00 -90.00   66
  6  \w    100.00 176.00   1.00    1.00    --  106.21 111.00   0.00   76
  7  \w     35.00 145.00   1.00    1.00    --  106.21 -15.00  90.00  110
  8  \w     37.00 109.00   1.00    1.00    --  106.21 -94.00  30.00   72
  9  \w     38.00 124.00   1.00    1.00    --  106.21 -45.00  90.00   86
 10  \w    100.00 176.00   1.00    1.00    --  106.21 111.00  30.00   76
 11  \w     39.00 133.00   1.00    1.00    --  106.21 -77.00 -30.00   94
 12  \w     39.00 133.00   1.00    1.00    --  106.21 -77.00-180.00   94
 13  \w     37.00 109.00   1.00    1.00    --  106.21 -94.00 120.00   72
 14  \w     89.00 175.00   1.00    1.00    --  106.21  45.00 -90.00   86
 15  \w     36.00 128.00   1.00    1.00    --  106.21 -30.00-120.00   92
 16  \w     37.00 119.00   1.00    1.00    --  106.21-128.00 -27.00   82
 17  \w     36.00 128.00   1.00    1.00    --  106.21 -30.00 -30.00   92
 18  \w   -104.00  -9.00   1.00    1.00    --  -36.04 -77.00 150.00   95
 19  \w   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0040264000
_diffrn_orient_matrix_UB_12      0.0035576000
_diffrn_orient_matrix_UB_13      0.1762747000
_diffrn_orient_matrix_UB_21      -0.1696766000
_diffrn_orient_matrix_UB_22      -0.0835200000
_diffrn_orient_matrix_UB_23      0.0309087000
_diffrn_orient_matrix_UB_31      0.1588139000
_diffrn_orient_matrix_UB_32      -0.1820997000
_diffrn_orient_matrix_UB_33      -0.0098407000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3582
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.498
_diffrn_reflns_theta_min         5.755
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0594
_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^)+(0.1027P)^2^+0.1612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1553
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1692
_reflns_number_total             1777
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01921_si_002.cif
_cod_data_source_block           wj-wj-wj0143-150k
_cod_depositor_comments          'Adding full bibliography for 4038792.cif.'
_cod_database_code               4038792
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00D), C00C(H00E), C00D(H00F), C00E(H00G), C00F(H00H)
2.b Idealised Me refined as rotating group:
 C005(H00A,H00B,H00C)
;
_shelx_res_checksum              69125
_shelx_hkl_checksum              73149
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.662
_oxdiff_exptl_absorpt_empirical_full_min 0.710