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_1545396
_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_moiety         'C16 H10 Cl N O2'
_chemical_formula_sum            'C16 H10 Cl N O2'
_chemical_formula_weight         283.70
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-06
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                78.039(2)
_cell_angle_beta                 87.320(2)
_cell_angle_gamma                63.031(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4540(4)
_cell_length_b                   7.9852(4)
_cell_length_c                   12.3366(6)
_cell_measurement_reflns_used    2007
_cell_measurement_temperature    100
_cell_measurement_theta_max      65.87
_cell_measurement_theta_min      3.67
_cell_volume                     639.29(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9262
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.327
_diffrn_reflns_theta_max         67.327
_diffrn_reflns_theta_min         3.668
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.649
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0675 before and 0.0484 after correction. The Ratio of minimum to maximum transmission is 0.7727. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0349P)^2^+0.3323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2227
_reflns_number_total             2238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00178_si_003.cif
_cod_data_source_block           cxy372_0m
_cod_depositor_comments
'Adding full bibliography for 1545396--1545397.cif.'
_cod_original_cell_volume        639.30(6)
_cod_database_code               1545396
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'