Chelation-assisted and steric-controlled selectivity in the Pd-catalyzed C-H/C-H oxidative coupling of indoles.
Vijaykumar, Muniyappa; Pradhan, Chandini; Gonnade, Rajesh G.; Punji, Benudhar; Chemical communications (Cambridge, England) 60 (2024) 13028–13031; doi:10.1039/d4cc03835e

data_7133860
_publ_section_title
;
 Chelation-assisted and steric-controlled selectivity in the Pd-catalyzed
 C-H/C-H oxidative coupling of indoles.
;
_journal_issue                   89
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13028
_journal_page_last               13031
_journal_paper_doi               10.1039/d4cc03835e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C40 H34 F6 N4 O6 Pd2, 3(CLCH2CH2CL)'
_chemical_formula_sum            'C46 H46 Cl6 F6 N3 O8 Pd2'
_chemical_formula_weight         1308.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'Difference Fourier'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-06-26 deposited with the CCDC.	2024-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                74.2790(10)
_cell_angle_beta                 75.9160(10)
_cell_angle_gamma                69.7240(10)
_cell_formula_units_Z            2
_cell_length_a                   11.1926(3)
_cell_length_b                   14.3110(4)
_cell_length_c                   15.3221(4)
_cell_measurement_reflns_used    9430
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.80
_cell_volume                     2185.49(10)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            61959
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         1.967
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    1.279
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_description       block
_exptl_crystal_F_000             1310
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloroethane'
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_platon_squeeze_details
;
The crystal structure contained three highly disordered dichloroethane 
solvent molecules.PLATON/SQUEEZE was used to correct the diffraction 
data for the contribution from disordered lattice solvent molecules. 
They have been treated as a diffuse contribution to the overall 
scattering without specific atom positions. 
The solvent accessible void volume per unit cell was 351 A3 (16%) 
and Electron Count/unit Cell was 151 e/A-3, estimated by PLATON. 
This electron count corresponds to three disordered dichloroethane molecules 
present in the unit cell. However, they have been included in
SFAC and UNIT instructions to get the correct molecular formula 
of the asymmetruc unit, formula weight, crystal density and F(000). 
;
_refine_diff_density_max         2.144
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         10805
_refine_ls_number_restraints     122
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0262P)^2^+4.7298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9883
_reflns_number_total             10805
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03835e2.cif
_cod_data_source_block           comp_27
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Direct Method' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7133856--7133864.cif.
;
_cod_database_code               7133860
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.872
_shelx_estimated_absorpt_t_max   0.927
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              42634
_shelx_hkl_checksum              58599
_shelx_fab_checksum              89408