Silver-promoted decarboxylative radical addition/annulation of oxamic acids with gem-difluoroolefins: concise access to CF<sub>2</sub>-containing 3,4-dihydroquinolin-2-ones.
Chen, Guojun; Li, Chenglong; Peng, Jianfeng; Yuan, Zeli; Liu, Peijun; Liu, Xiaozu; Organic & biomolecular chemistry 17 (2019) 8527–8532; doi:10.1039/c9ob01236b

data_7157063
_publ_section_title
;
 Silver-promoted decarboxylative radical addition/annulation of oxamic
 acids with gem-difluoroolefins: concise access to
 CF<sub>2</sub>-containing 3,4-dihydroquinolin-2-ones.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8527
_journal_page_last               8532
_journal_paper_doi               10.1039/c9ob01236b
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C17 H12 F2 N2 O'
_chemical_formula_sum            'C17 H12 F2 N2 O'
_chemical_formula_weight         298.29
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-24 deposited with the CCDC.    2019-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.510(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9400(7)
_cell_length_b                   10.9431(8)
_cell_length_c                   14.3252(12)
_cell_measurement_reflns_used    3187
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.7340
_cell_measurement_theta_min      2.9740
_cell_volume                     1373.27(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.860
_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    -80.00  13.00   1.00    2.00    --  -11.59 -57.00  60.00   93
  2  \w    -40.00  59.00   1.00    2.00    --  -11.59  57.00-150.00   99
  3  \w    -15.00  35.00   1.00    2.00    --   11.74  77.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0215168000
_diffrn_orient_matrix_UB_12      -0.0093857000
_diffrn_orient_matrix_UB_13      0.0498440000
_diffrn_orient_matrix_UB_21      -0.0729968000
_diffrn_orient_matrix_UB_22      -0.0247668000
_diffrn_orient_matrix_UB_23      0.0005662000
_diffrn_orient_matrix_UB_31      0.0271876000
_diffrn_orient_matrix_UB_32      -0.0593056000
_diffrn_orient_matrix_UB_33      -0.0081570000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8740
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.564
_diffrn_reflns_theta_min         2.360
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0411P)^2^+0.6218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2615
_reflns_number_total             3304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01236b2.cif
_cod_data_source_block           c028
_cod_depositor_comments          'Adding full bibliography for 7157063.cif.'
_cod_database_code               7157063
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C12(H12), C14(H14), C5(H5), C8(H8), C11(H11), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.678