Iridium(III)-Catalyzed C-H Amidation of Nitrones with Dioxazolones.
Mi, Xia; Feng, Weisheng; Pi, Chao; Cui, Xiuling; The Journal of organic chemistry 84 (2019) 5305–5312; doi:10.1021/acs.joc.9b00300

data_4034312
_publ_section_title
;
 Iridium(III)-Catalyzed C-H Amidation of Nitrones with Dioxazolones.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5305
_journal_page_last               5312
_journal_paper_doi               10.1021/acs.joc.9b00300
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H20 N2 O2'
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_weight         296.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-09-27
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.922(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            32
_cell_length_a                   23.6610(5)
_cell_length_b                   23.7462(5)
_cell_length_c                   25.8874(6)
_cell_measurement_reflns_used    5515
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5390
_cell_measurement_theta_min      3.6130
_cell_volume                     13674.6(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -42.00    6.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000  -30.0000 48

  2 omega    8.00   38.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000  120.0000 30

  3 omega  -70.00  -28.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000  120.0000 42

  4 omega   57.00  104.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 47

  5 omega   67.00  104.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  150.0000 37

  6 omega   58.00  109.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 51

  7 omega   14.00   52.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   90.0000 38

  8 omega   65.00  100.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   90.0000 35

  9 omega   58.00  110.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 52

 10 omega   59.00  102.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 43

 11 omega   43.00  135.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 92

 12 omega   42.00   95.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 53

 13 omega   38.00  105.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 67

 14 omega   43.00   96.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 53

 15 omega   92.00  120.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 28

 16 omega  117.00  173.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 56

 17 omega   38.00   75.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 37

 18 omega   83.00  175.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0218657000
_diffrn_orient_matrix_UB_12      -0.0035338000
_diffrn_orient_matrix_UB_13      0.0631790000
_diffrn_orient_matrix_UB_21      0.0557498000
_diffrn_orient_matrix_UB_22      0.0352840000
_diffrn_orient_matrix_UB_23      0.0032487000
_diffrn_orient_matrix_UB_31      -0.0347847000
_diffrn_orient_matrix_UB_32      0.0543202000
_diffrn_orient_matrix_UB_33      0.0020276000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25203
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         3.63
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5056
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1609
_refine_ls_number_reflns         17297
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0804P)^2^+1.3271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1719
_reflns_number_gt                11063
_reflns_number_total             17297
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b00300_si_002.cif
_cod_data_source_block           201809383
_cod_database_code               4034312
_chemical_oxdiff_formula         C15H15O3N2
_reflns_odcompleteness_completeness 99.48
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), N1(H1), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C9A(H9A),
 C10A(H10A), C11A(H11A), C12A(H12A), C14A(H14A), N1A(H1A), C3B(H3B), C4B(H4B),
 C5B(H5B), C6B(H6B), C7B(H7B), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B),
 C14B(H14B), N1B(H1B), C3C(H3C), C4C(H4C), C5C(H5C), C6C(H6C), C7C(H7C),
 C9C(H9C), C10C(H10C), C11C(H11C), C12C(H12C), C14C(H14C), N1C(H1C), C3D(H3D),
 C4D(H4D), C5D(H5D), C6D(H6D), C7D(H7D), C9D(H9D), C10D(H10D), C11D(H11D),
 C12D(H12D), C14D(H14D), N1D(H1D), C3E(H3E), C4E(H4E), C5E(H5E), C6E(H6E),
 C7E(H7E), C9E(H9E), C10E(H10E), C11E(H11E), C12E(H12E), C14E(H14E), N1E(H1E),
 C3F(H3F), C4F(H4F), C5F(H5F), C6F(H6F), C7F(H7F), C9F(H9F), C10F(H10F),
 C11F(H11F), C12F(H12F), C14F(H14F), N1F(H1F), C3G(H3G), C4G(H4G), C5G(H5G),
 C6G(H6G), C7G(H7G), C9G(H9G), C10G(H10G), C11G(H11G), C12G(H12G), C14G(H14G),
 N1G(H1G)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C16A(H16D,H16E,
 H16F), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F), C16B(H16G,H16H,H16I),
 C17B(H17G,H17H,H17I), C18B(H18G,H18H,H18I), C16C(H16J,H16K,H16L), C17C(H17J,
 H17K,H17L), C18C(H18J,H18K,H18L), C16D(H16M,H16N,H16O), C17D(H17M,H17N,H17O),
 C18D(H18M,H18N,H18O), C16E(H16P,H16Q,H16R), C17E(H17P,H17Q,H17R), C18E(H18P,
 H18Q,H18R), C16F(H16S,H16T,H16U), C17F(H17S,H17T,H17U), C18F(H18S,H18T,H18U),
 C16G(H16V,H16W,H16X), C17G(H17V,H17W,H17X), C18G(H18V,H18W,H18X)
;
_olex2_submission_special_instructions 'No special instructions were received'