Co(III)-Catalyzed C-H Amidation of Nitrogen Containing Heterocycles with Dioxazolones under Mild Condition.
Dhiman, Ankit Kumar; Thakur, Ankita; Kumar, Inder; Kumar, Rakesh; Sharma, Upendra; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01237

data_4038551
_publ_section_title
;
 Co(III)-Catalyzed C-H Amidation of Nitrogen Containing Heterocycles with
 Dioxazolones under Mild Condition.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01237
_journal_year                    2020
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-12-11
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.400(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1128(9)
_cell_length_b                   9.3254(11)
_cell_length_c                   17.1572(18)
_cell_measurement_reflns_used    1370
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.4300
_cell_measurement_theta_min      5.2330
_cell_volume                     1276.7(3)
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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    -49.00   1.00   1.00    1.00    --   25.69 -57.00-180.00   50
  2  \w      4.00  75.00   1.00    1.00    --   25.69 -99.00 -60.00   71
  3  \w      4.00  63.00   1.00    1.00    --   25.69 -57.00-180.00   59
  4  \w     31.00 124.00   1.00    8.00    --   66.85  63.00 -60.00   93
  5  \w    100.00 143.00   1.00    8.00    --   66.85 111.00-120.00   43
  6  \w     -6.00  19.00   1.00    8.00    --   66.85 -91.00 -90.00   25
  7  \w    122.00 148.00   1.00    8.00    --   66.85 178.00   0.00   26
  8  \w     45.00 150.00   1.00    8.00    --   66.85  77.00 150.00  105
  9  \w     47.00 103.00   1.00    8.00    --   66.85 -91.00 -90.00   56
 10  \w     76.00 103.00   1.00   30.00    --  108.00-104.00 -60.00   27
 11  \w     24.00  64.00   1.00   30.00    --  108.00-104.00 -60.00   40
 12  \w     32.00 103.00   1.00   30.00    --  108.00-104.00-180.00   71
 13  \w     42.00  80.00   1.00   30.00    --  108.00 -43.00  60.00   38
 14  \w     25.00  82.00   1.00   30.00    --  108.00 -32.00-180.00   57
 15  \w    111.00 175.00   1.00   30.00    --  108.00 104.00 120.00   64
 16  \w     74.00 104.00   1.00   30.00    --  108.00-104.00  90.00   30
 17  \w     24.00  58.00   1.00   30.00    --  108.00-104.00  90.00   34
 18  \w    144.00 173.00   1.00   30.00    --  108.00 -32.00-180.00   29
 19  \w     86.00 118.00   1.00   30.00    --  108.00 -32.00-180.00   32
 20  \w     94.00 144.00   1.00   30.00    --  108.00 -43.00  60.00   50
 21  \w     25.00  64.00   1.00   30.00    --  108.00-104.00 120.00   39
 22  \w     75.00 103.00   1.00   30.00    --  108.00-104.00   0.00   28
 23  \w    117.00 176.00   1.00   30.00    --  108.00 104.00  90.00   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1915883000
_diffrn_orient_matrix_UB_12      -0.0091723000
_diffrn_orient_matrix_UB_13      -0.0268452000
_diffrn_orient_matrix_UB_21      0.0070004000
_diffrn_orient_matrix_UB_22      -0.1630108000
_diffrn_orient_matrix_UB_23      0.0148585000
_diffrn_orient_matrix_UB_31      -0.0240655000
_diffrn_orient_matrix_UB_32      0.0253815000
_diffrn_orient_matrix_UB_33      0.0858835000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3874
_diffrn_reflns_theta_full        66.84
_diffrn_reflns_theta_max         66.84
_diffrn_reflns_theta_min         5.24
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Square
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+0.1128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1289
_reflns_number_gt                1775
_reflns_number_total             2204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c01237_si_003.cif
_cod_data_source_block           usanb3_rt_cu
_cod_original_cell_volume        1276.7(2)
_cod_database_code               4038551
_chemical_oxdiff_formula         'C64 H48 N8 O8'
_reflns_odcompleteness_completeness 96.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C5(H5), C11(H11), C15(H15), C4(H4), C13(H13), C10(H10),
 C14(H14), C1(H1A), C3(H3), C2(H2)
;
_olex2_date_sample_data_collection 2019-12-10
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.803