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_7133858
_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         'C36 H32 Cl2 N4 O2, 0.5(CH3CH2COOCH3)'
_chemical_formula_sum            'C38 H36 Cl2 N4 O3'
_chemical_formula_weight         667.61
_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                93.7000(10)
_cell_angle_beta                 100.6210(10)
_cell_angle_gamma                107.1050(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1994(3)
_cell_length_b                   13.5661(5)
_cell_length_c                   14.2548(5)
_cell_measurement_reflns_used    9757
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.63
_cell_measurement_theta_min      2.51
_cell_volume                     1657.77(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 0.989
_diffrn_measured_fraction_theta_max 0.846
_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  0.0455
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            52079
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.987
_diffrn_reflns_theta_min         2.508
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6384
_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    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             700
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_platon_squeeze_details
;
The crystal structure contained disordered half ethyl acetate 
solvent molecule.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 164 A3 
and Electron Count/unit Cell was 46 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         0.679
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         11451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0469
_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^+1.1095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9434
_reflns_number_total             11451
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03835e2.cif
_cod_data_source_block           comp_17
_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               7133858
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.974
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              68294
_shelx_hkl_checksum              7140
_shelx_fab_checksum              7824