Oxidation of β-Ketoamides: The Synthesis of Vicinal Tricarbonyl Amides.
Liu, Yueyang; Zhang, Zhiguo; Wan, Yameng; Zhang, Guisheng; Li, Zhonglian; Bi, Jingjing; Ma, Nana; Liu, Tong-Xin; Liu, Qingfeng; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.6b03062

data_4032343
_publ_section_title
;
 Oxidation of \b-Ketoamides: The Synthesis of Vicinal Tricarbonyl Amides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.6b03062
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H10 Cl N O3'
_chemical_formula_sum            'C15 H10 Cl N O3'
_chemical_formula_weight         287.69
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-02-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.76624(17)
_cell_length_b                   11.7165(3)
_cell_length_c                   19.6213(6)
_cell_measurement_reflns_used    1016
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      70.1730
_cell_measurement_theta_min      4.4940
_cell_volume                     1325.62(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega  -27.00    0.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -120.0000 27

  2 omega   34.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -120.0000 34

  3 omega  -47.00   30.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  -90.0000 77

  4 omega  -43.00  -18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   61.0000  -60.0000 25

  5 omega  -36.00    1.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000  -60.0000 37

  6 omega  -91.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000  -60.0000 42

  7 omega  -12.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   61.0000  -60.0000 34

  8 omega  106.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -30.0000 72

  9 omega   39.00   81.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 42

 10 omega   51.00  102.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 51

 11 omega   54.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 36

 12 omega   39.00  119.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000  150.0000 80
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0312991000
_diffrn_orient_matrix_UB_12      -0.1273164000
_diffrn_orient_matrix_UB_13      0.0173168000
_diffrn_orient_matrix_UB_21      -0.0000203000
_diffrn_orient_matrix_UB_22      -0.0291320000
_diffrn_orient_matrix_UB_23      -0.0766301000
_diffrn_orient_matrix_UB_31      0.2651397000
_diffrn_orient_matrix_UB_32      -0.0149147000
_diffrn_orient_matrix_UB_33      0.0020519000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3024
_diffrn_reflns_theta_full        72.32
_diffrn_reflns_theta_max         72.32
_diffrn_reflns_theta_min         4.40
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       0.0034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+0.2383P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                1801
_reflns_number_total             2065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b03062_si_002.cif
_cod_data_source_block           20150235
_cod_original_cell_volume        1325.61(7)
_cod_database_code               4032343
_chemical_oxdiff_formula         C20H20N4O4Cl1
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'