"One-Pot" Approach to 8-Acylated 2-Quinolinones via Palladium-Catalyzed Regioselective Acylation of Quinoline N-Oxides.
Chen, Xiaopei; Cui, Xiuling; Wu, Yangjie; Organic letters 18 (2016) 2411–2414; doi:10.1021/acs.orglett.6b00923

data_1543811
_publ_section_title
;
 &quot;One-Pot&quot; Approach to 8-Acylated 2-Quinolinones via
 Palladium-Catalyzed Regioselective Acylation of Quinoline N-Oxides.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2411
_journal_page_last               2414
_journal_paper_doi               10.1021/acs.orglett.6b00923
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H11 N O2'
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-10
_audit_creation_method
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Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
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_cell_angle_beta                 90.00
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_cell_length_a                   7.0519(3)
_cell_length_b                   23.5069(9)
_cell_length_c                   7.5339(3)
_cell_measurement_reflns_used    994
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.6620
_cell_measurement_theta_min      6.1200
_cell_volume                     1248.88(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   -3.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  150.0000 28

  2 omega   -1.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000   90.0000 30

  3 omega   -5.00   25.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  -60.0000 30

  4 omega -113.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   30.0000 101

  5 omega  -38.00   -4.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000 -180.0000 34

  6 omega    3.00   30.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000 -180.0000 27

  7 omega   54.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 32

  8 omega   50.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 36

  9 omega   65.00  100.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 35

 10 omega   50.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 44

 11 omega   41.00   95.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 54

 12 omega   42.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 66

 13 omega  -77.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -120.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0521033000
_diffrn_orient_matrix_UB_12      0.0633633000
_diffrn_orient_matrix_UB_13      0.0178369000
_diffrn_orient_matrix_UB_21      -0.0424549000
_diffrn_orient_matrix_UB_22      0.0026553000
_diffrn_orient_matrix_UB_23      -0.2004131000
_diffrn_orient_matrix_UB_31      -0.2079254000
_diffrn_orient_matrix_UB_32      -0.0164559000
_diffrn_orient_matrix_UB_33      0.0364659000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2492
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         6.17
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1570
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0525P)^2^+0.0556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1018
_reflns_number_gt                1355
_reflns_number_total             1570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00923_si_002.cif
_cod_data_source_block           201412267
_cod_original_cell_volume        1248.89(9)
_cod_database_code               1543811
_chemical_oxdiff_formula         c20h20n4o4
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_olex2_date_sample_data_collection 2015-12-09
_olex2_submission_special_instructions 'No special instructions were received'