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_4037837
_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_formula_moiety         'C34 H26 Br2 N2 O6 Pd, 1.33(H2 O)'
_chemical_formula_sum            'C34 H28.67 Br2 N2 O7.33 Pd'
_chemical_formula_weight         848.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.433(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9231(3)
_cell_length_b                   10.1765(2)
_cell_length_c                   15.8477(4)
_cell_measurement_reflns_used    8815
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3870
_cell_measurement_theta_min      3.4500
_cell_volume                     3207.31(11)
_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 0.999
_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    -51.00  70.00   1.00   15.27    --  -19.00  38.00 -60.00  121
  2  \w   -108.00  16.00   1.00   15.27    --  -19.00 -57.00  30.00  124
  3  \w    -54.00  70.00   1.00   15.27    --  -19.00  60.00-180.00  124
  4  \w    -51.00   2.00   1.00   15.27    --  -19.00  38.00 120.00   53
  5  \w   -108.00  13.00   1.00   15.27    --  -19.00 -38.00-180.00  121
;
_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      -0.0142154000
_diffrn_orient_matrix_UB_12      -0.0222457000
_diffrn_orient_matrix_UB_13      -0.0395646000
_diffrn_orient_matrix_UB_21      -0.0321590000
_diffrn_orient_matrix_UB_22      -0.0023413000
_diffrn_orient_matrix_UB_23      0.0168295000
_diffrn_orient_matrix_UB_31      -0.0059129000
_diffrn_orient_matrix_UB_32      0.0660259000
_diffrn_orient_matrix_UB_33      -0.0127490000
_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  0.0463
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20357
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.498
_diffrn_reflns_theta_min         3.194
_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    3.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70439
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_description       block
_exptl_crystal_F_000             1685
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4057
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+6.7651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3566
_reflns_number_total             4057
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03321_si_002.cif
_cod_data_source_block           2019acc0020_k1_100k
_cod_database_code               4037837
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C12 H12 N2 O2 Pd1 Br1'
_chemical_oxdiff_usercomment     AH_05_410_Br
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 94.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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, All O(H) groups
2. Restrained distances
 H4A_$1-H4A
 1.4 with sigma of 0.02
3. Others
 Fixed Sof: O5(0.16667) H5A(0.33333)
4.a Free rotating group:
 O5(H5A)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              10127
_shelx_hkl_checksum              95138
_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 AH_05_408_Br
_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 2.924
_oxdiff_exptl_absorpt_empirical_full_min 0.550