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_4029865
_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         'C23 H16 Br N O2'
_chemical_formula_sum            'C23 H16 Br N O2'
_chemical_formula_weight         418.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90.00
_cell_angle_beta                 104.086(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3678(4)
_cell_length_b                   9.9254(3)
_cell_length_c                   18.3510(6)
_cell_measurement_reflns_used    3363
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1410
_cell_measurement_theta_min      4.3950
_cell_volume                     1831.62(11)
_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 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -50.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -30.0000 39

  2 omega  -59.00  -34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000   90.0000 25

  3 omega -111.00  -57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  -60.0000 54

  4 omega  -30.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -180.0000 60

  5 omega  -49.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  -90.0000 72

  6 omega    0.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000   90.0000 26

  7 omega   -2.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -150.0000 30

  8 omega   43.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -150.0000 54

  9 omega   90.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -150.0000 81

 10 omega   41.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 45

 11 omega   39.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 33

 12 omega   42.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 54

 13 omega   66.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 31

 14 omega   45.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 46

 15 omega   39.00   64.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 25

 16 omega   43.00  113.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -60.0000 70

 17 omega   41.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 49

 18 omega  140.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -120.0000 38

 19 omega  -72.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000   60.0000 98

 20 omega   35.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  150.0000 84
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1361118000
_diffrn_orient_matrix_UB_12      -0.0490779000
_diffrn_orient_matrix_UB_13      -0.0092154000
_diffrn_orient_matrix_UB_21      0.0634911000
_diffrn_orient_matrix_UB_22      0.0371155000
_diffrn_orient_matrix_UB_23      0.0824740000
_diffrn_orient_matrix_UB_31      -0.0303668000
_diffrn_orient_matrix_UB_32      -0.1424292000
_diffrn_orient_matrix_UB_33      0.0246645000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6960
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         4.40
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79040
_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    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00152(13)
_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   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+0.7250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0938
_reflns_number_gt                2724
_reflns_number_total             3270
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501301t_si_002.cif
_cod_data_source_block           201309137
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029864--4029865.cif.
;
_cod_original_cell_volume        1831.62(10)
_cod_database_code               4029865
_chemical_oxdiff_formula         C20H20N4O4
_reflns_odcompleteness_completeness 99.91
_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), C23(H23), C22(H22), C20(H20), C19(H19),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;