Silver-Catalyzed Radical Tandem Cyclization: An Approach to Direct Synthesis of 3-Acyl-4-arylquinolin-2(1H)-ones.
Mai, Wen-Peng; Sun, Gang-Chun; Wang, Ji-Tao; Song, Ge; Mao, Pu; Yang, Liang-Ru; Yuan, Jin-Wei; Xiao, Yong-Mei; Qu, Ling-Bo; The Journal of organic chemistry 79 (2014) 8094–8102; doi:10.1021/jo501301t

data_4029864
_publ_section_title
;
 Silver-Catalyzed Radical Tandem Cyclization: An Approach to Direct
 Synthesis of 3-Acyl-4-arylquinolin-2(1H)-ones.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8094
_journal_page_last               8102
_journal_paper_doi               10.1021/jo501301t
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C24 H19 N O2'
_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_weight         353.40
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-12
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                105.945(7)
_cell_angle_beta                 109.988(6)
_cell_angle_gamma                99.912(6)
_cell_formula_units_Z            2
_cell_length_a                   9.5219(5)
_cell_length_b                   9.7304(8)
_cell_length_c                   11.5747(9)
_cell_measurement_reflns_used    3095
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1820
_cell_measurement_theta_min      4.3440
_cell_volume                     926.09(14)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   29.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 26

  2 omega -111.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000   60.0000 90

  3 omega  -52.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000   30.0000 58

  4 omega -115.00  -74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -30.0000  -30.0000 41

  5 omega  -63.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000 -150.0000 89

  6 omega  -97.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000  -90.0000 69

  7 omega  -17.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  150.0000 45

  8 omega -104.00  -66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -30.0000 38

  9 omega   32.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -90.0000 81

 10 omega   89.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   90.0000 89

 11 omega   58.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 25

 12 omega   47.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 59

 13 omega   44.00  140.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -30.0000 96

 14 omega   46.00   84.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 38

 15 omega   51.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  120.0000 59

 16 omega  149.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   30.0000 25

 17 omega   93.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   30.0000 26

 18 omega   42.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 48

 19 omega   84.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -131.0000 -154.0000 30

 20 omega   43.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -131.0000 -154.0000 26

 21 omega   42.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 39

 22 omega   89.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 26

 23 omega  148.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -120.0000 28

 24 omega   40.00   75.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 35

 25 omega   41.00  159.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000   60.0000 118

 26 omega   50.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 55

 27 omega   -4.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  120.0000 46

 28 omega  -49.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  -30.0000 79

 29 omega -111.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  120.0000 90

 30 omega -113.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000    0.0000 101

 31 omega   35.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -150.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0038283000
_diffrn_orient_matrix_UB_12      -0.1090465000
_diffrn_orient_matrix_UB_13      0.0748027000
_diffrn_orient_matrix_UB_21      0.0874200000
_diffrn_orient_matrix_UB_22      0.1327613000
_diffrn_orient_matrix_UB_23      0.1320663000
_diffrn_orient_matrix_UB_31      -0.1574681000
_diffrn_orient_matrix_UB_32      0.0130188000
_diffrn_orient_matrix_UB_33      0.0037798000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6658
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         4.36
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95283
_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    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0161(12)
_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   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0603P)^2^+0.0543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1142
_reflns_number_gt                2757
_reflns_number_total             3306
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501301t_si_001.cif
_cod_data_source_block           201309138
_cod_depositor_comments
'Adding full bibliography for 4029864--4029865.cif.'
_cod_original_cell_volume        926.09(11)
_cod_database_code               4029864
_chemical_oxdiff_formula         C24H19NO2
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C24(H24A,H24B,H24C)
;