Well-Defined Palladium N-Heterocyclic Carbene Complexes: Direct C‒H Bond Arylation of Heteroarenes
Kumar, Anuj; Kumar, Manoj; Verma, Akhilesh K.; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c02024

data_4038898
_publ_section_title
;
 Well-Defined Palladium N-Heterocyclic Carbene Complexes: Direct C--H Bond
 Arylation of Heteroarenes
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c02024
_journal_year                    2020
_chemical_formula_moiety         'C51 H47 Cl2 N2 P Pd'
_chemical_formula_sum            'C51 H47 Cl2 N2 P Pd'
_chemical_formula_weight         896.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-12-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.969(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5895(5)
_cell_length_b                   14.6791(6)
_cell_length_c                   19.4121(7)
_cell_measurement_reflns_used    11162
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.599
_cell_measurement_theta_min      3.070
_cell_volume                     4425.6(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            45098
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.599
_diffrn_reflns_theta_min         3.070
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       needle
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         11162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+3.2425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1024
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8706
_reflns_number_total             11162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c02024_si_004.cif
_cod_data_source_block           av_ak_94b
_cod_database_code               4038898
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C34B(0.5) H34A(0.5) H34B(0.5) C35B(0.5) H35A(0.5) H35B(0.5)
 H35C(0.5) H40C(0.5) H40D(0.5) H40A(0.5) H40B(0.5) C41B(0.5) H41A(0.5)
 H41B(0.5) H41C(0.5) H44C(0.5) H44D(0.5) H44A(0.5) H44B(0.5) C45B(0.5)
 H45A(0.5) H45B(0.5) H45C(0.5) C35A(0.5) H35D(0.5) H35E(0.5) H35F(0.5)
 C34A(0.5) H34C(0.5) H34D(0.5) C41A(0.5) H41D(0.5) H41E(0.5) H41F(0.5)
 C45A(0.5) H45D(0.5) H45E(0.5) H45F(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C34B(H34A,H34B), C40(H40C,H40D), C40(H40A,H40B), C44(H44C,H44D), C44(H44A,
 H44B), C50(H50A,H50B), C34A(H34C,H34D)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C36(H36), C37(H37),
 C38(H38), C46(H46), C47(H47), C48(H48)
3.c Idealised Me refined as rotating group:
 C35B(H35A,H35B,H35C), C41B(H41A,H41B,H41C), C45B(H45A,H45B,H45C), C51(H51A,
 H51B,H51C), C35A(H35D,H35E,H35F), C41A(H41D,H41E,H41F), C45A(H45D,H45E,H45F)
;
_shelx_res_checksum              41328
_shelx_hkl_checksum              56932
_olex2_submission_special_instructions 'No special instructions were received'