Direct C5-Arylation Reaction between Imidazoles and Aryl Chlorides Catalyzed by Palladium Complexes with Phosphines and N-Heterocyclic Carbenes
Kumar, P. Vijaya; Lin, Wu-Shien; Shen, Jiun-Shian; Nandi, Debkumar; Lee, Hon Man; Organometallics 30 (2011) 5160–; doi:10.1021/om200490k

data_4065000
_publ_section_title
;
 Direct C5-Arylation Reaction between Imidazoles and Aryl Chlorides
 Catalyzed by Palladium Complexes with Phosphines and N-Heterocyclic
 Carbenes
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              5160
_journal_paper_doi               10.1021/om200490k
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         '2(C39 H55 N2 O4 P Pd), C4 H8 O, 2(H2 O)'
_chemical_formula_sum            'C82 H122 N4 O11 P2 Pd2'
_chemical_formula_weight         1614.58
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.823(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.5004(9)
_cell_length_b                   17.7544(13)
_cell_length_c                   19.0156(13)
_cell_measurement_reflns_used    4467
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.2
_cell_measurement_theta_min      2.5
_cell_volume                     4406.2(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 1999)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_sigmaI/netI    0.1105
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            51334
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.59
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_T_max  0.9518
_exptl_absorpt_correction_T_min  0.8812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.508
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       0.0082(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         9610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1287P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2354
_reflns_number_gt                5623
_reflns_number_total             9610
_reflns_threshold_expression     I>2\s
_cod_data_source_file            om200490k_si_002.cif
_cod_data_source_block           1b
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4065000