Ether-imidazolium carbenes for suzuki-miyaura cross-coupling of heteroaryl chlorides with aryl/heteroarylboron reagents.
Kuriyama, Masami; Matsuo, Seira; Shinozawa, Mina; Onomura, Osamu; Organic letters 15 (2013) 2716–2719; doi:10.1021/ol4010189

data_1512080
_publ_section_title
;
 Ether-imidazolium carbenes for suzuki-miyaura cross-coupling of
 heteroaryl chlorides with aryl/heteroarylboron reagents.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2716
_journal_page_last               2719
_journal_paper_doi               10.1021/ol4010189
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C55 H58 Cl4 N4 O2 Pd'
_chemical_formula_sum            'C55 H58 Cl4 N4 O2 Pd'
_chemical_formula_weight         1055.30
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                75.262(6)
_cell_angle_beta                 79.729(7)
_cell_angle_gamma                70.965(5)
_cell_formula_units_Z            2
_cell_length_a                   11.3639(13)
_cell_length_b                   13.2788(15)
_cell_length_c                   18.587(2)
_cell_measurement_reflns_used    6821
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.04
_cell_volume                     2550.2(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32067
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1092.00
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.310
_refine_diff_density_min         -1.640
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     608
_refine_ls_number_reflns         11600
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0554P)^2^+4.4007P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                9371
_reflns_number_total             11600
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol4010189_si_002.cif
_cod_data_source_block           1189a_compound_7d
_cod_database_code               1512080