Transition-Metal-Free β-C-H Bond Carbonylation of Enamides or Amides with a Trifluoromethyl Group as CO Surrogate for the Synthesis of 1,3-Oxazin-6-ones.
Song, Ping; Yu, Peng; Lin, Jin-Shun; Li, Yiqun; Yang, Ning-Yuan; Liu, Xin-Yuan; Organic letters 19 (2017) 1330–1333; doi:10.1021/acs.orglett.7b00178

data_1545397
_publ_section_title
;
 Transition-Metal-Free \b-C-H Bond Carbonylation of Enamides or Amides
 with a Trifluoromethyl Group as CO Surrogate for the Synthesis of
 1,3-Oxazin-6-ones.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1330
_journal_page_last               1333
_journal_paper_doi               10.1021/acs.orglett.7b00178
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C20 H16 F3 N O2'
_chemical_formula_weight         359.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                104.277(7)
_cell_angle_beta                 95.031(7)
_cell_angle_gamma                106.485(7)
_cell_formula_units_Z            2
_cell_length_a                   7.3942(2)
_cell_length_b                   9.7789(3)
_cell_length_c                   12.8841(9)
_cell_measurement_reflns_used    8735
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.40
_cell_measurement_theta_min      6.70
_cell_volume                     853.17(9)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11853
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.367
_diffrn_reflns_theta_min         6.682
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.249
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0667
_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^)+(0.0957P)^2^+0.2017P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2060
_reflns_number_total             3004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00178_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1545396--1545397.cif.'
_cod_original_cell_volume        853.17(8)
_cod_database_code               1545397
_shelxl_version_number           2013-2
_shelx_res_checksum              57449
_shelx_hkl_checksum              26880