"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_1543810
_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_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
_audit_creation_date             2015-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.8024(9)
_cell_length_b                   7.7552(4)
_cell_length_c                   17.7401(12)
_cell_measurement_reflns_used    1706
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0390
_cell_measurement_theta_min      3.4540
_cell_volume                     2449.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

--------------------------------------------------------------------------
  1  \w    -25.00  13.00   1.00   21.00    --  -14.59 -99.00-150.00   38
  2  \w    -31.00  51.00   1.00   21.00    --  -14.59  57.00  30.00   82
  3  \w    -22.00   5.00   1.00   21.00    --   17.71 -99.00 -90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0369419000
_diffrn_orient_matrix_UB_12      -0.0031165000
_diffrn_orient_matrix_UB_13      0.0149558000
_diffrn_orient_matrix_UB_21      0.0143377000
_diffrn_orient_matrix_UB_22      0.0192505000
_diffrn_orient_matrix_UB_23      0.0363326000
_diffrn_orient_matrix_UB_31      -0.0043685000
_diffrn_orient_matrix_UB_32      0.0893477000
_diffrn_orient_matrix_UB_33      -0.0073021000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7073
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.484
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.352
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0391P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2425
_reflns_number_total             3815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00923_si_003.cif
_cod_data_source_block           201512165
_cod_database_code               1543810
_chemical_oxdiff_formula         C20H20N3O2
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1(2) 0(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C1'(H1'), C2'(H2'), C3'(H3'), C7'(H7'), C8'(H8'), C9'(H9'),
  C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C16'(H16')
;
_shelx_res_checksum              92755
_shelx_hkl_checksum              74609
_shelx_shelxl_version_number     2014/7
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.082
_oxdiff_exptl_absorpt_empirical_full_min 0.900