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_1512081
_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         'C48 H60 Cl2 N4 O2 Pd'
_chemical_formula_sum            'C48 H60 Cl2 N4 O2 Pd'
_chemical_formula_weight         902.33
_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                69.341(14)
_cell_angle_beta                 87.28(3)
_cell_angle_gamma                87.50(3)
_cell_formula_units_Z            1
_cell_length_a                   9.525(7)
_cell_length_b                   9.705(6)
_cell_length_c                   13.059(8)
_cell_measurement_reflns_used    3629
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.04
_cell_volume                     1127.8(13)
_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 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0635
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9504
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472.00
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         2.120
_refine_diff_density_min         -1.350
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     259
_refine_ls_number_reflns         5129
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0802
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0720P)^2^+4.5196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1901
_reflns_number_gt                3763
_reflns_number_total             5129
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol4010189_si_002.cif
_cod_data_source_block           1244a_compound_7e
_cod_original_cell_volume        1127.8(12)
_cod_database_code               1512081