One-Pot Cross-Coupling/C–H Functionalization Reactions: Quinoline as a Substrate and Ligand through N–Pd Interaction
Shanahan, Rachel M.; Hickey, Aobha; Bateman, Lorraine M.; Light, Mark E.; McGlacken, Gerard P.; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.9b03321

data_4037834
_publ_section_title
;
 One-Pot Cross-Coupling/C--H Functionalization Reactions: Quinoline as a
 Substrate and Ligand through N--Pd Interaction
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03321
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H13 N O'
_chemical_formula_sum            'C21 H13 N O'
_chemical_formula_weight         295.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.868(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4470(2)
_cell_length_b                   6.2048(2)
_cell_length_c                   20.0037(5)
_cell_measurement_reflns_used    5920
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6440
_cell_measurement_theta_min      3.0630
_cell_volume                     1415.66(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_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(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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   -108.00  16.00   1.00   22.50    --  -19.00 -60.00 -90.00  124
  2  \w    -54.00  70.00   1.00   22.50    --  -19.00  60.00  60.00  124
  3  \w   -108.00  16.00   1.00   22.50    --  -19.00 -57.00 150.00  124
  4  \w   -108.00 -45.00   1.00   22.50    --  -19.00 -60.00  30.00   63
  5  \w    -54.00  70.00   1.00   22.50    --  -19.00  60.00-120.00  124
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0005978000
_diffrn_orient_matrix_UB_12      0.0174237000
_diffrn_orient_matrix_UB_13      0.0350323000
_diffrn_orient_matrix_UB_21      0.0618629000
_diffrn_orient_matrix_UB_22      0.0116055000
_diffrn_orient_matrix_UB_23      0.0027728000
_diffrn_orient_matrix_UB_31      -0.0062856000
_diffrn_orient_matrix_UB_32      0.1123241000
_diffrn_orient_matrix_UB_33      -0.0057224000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19713
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.495
_diffrn_reflns_theta_min         3.066
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6982
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0427P)^2^+0.0040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                5764
_reflns_number_total             6982
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03321_si_002.cif
_cod_data_source_block           2019acc0015_k1_100k
_cod_database_code               4037834
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C22 H22 N1 O1'
_chemical_oxdiff_usercomment     RMS-269
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 94.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C8B(H8B), C12B(H12B), C13B(H13B),
 C15B(H15B), C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B),
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C8A(H8A), C12A(H12A), C13A(H13A),
 C15A(H15A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A)
;
_shelx_res_checksum              31358
_shelx_hkl_checksum              83767
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id RMS-269
_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 2.604
_oxdiff_exptl_absorpt_empirical_full_min 0.527