Sterically Encumbered Tetraarylimidazolium Carbene Pd-PEPPSI Complexes: Highly Efficient Direct Arylation of Imidazoles with Aryl Bromides under Aerobic Conditions
He, Xu-Xian; Li, Yinwu; Ma, Bei-Bei; Ke, Zhuofeng; Liu, Feng-Shou; Organometallics 35 (2016) 2655–; doi:10.1021/acs.organomet.6b00391

data_4088761
_publ_section_title
;
 Sterically Encumbered Tetraarylimidazolium Carbene Pd-PEPPSI Complexes:
 Highly Efficient Direct Arylation of Imidazoles with Aryl Bromides under
 Aerobic Conditions
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              2655
_journal_paper_doi               10.1021/acs.organomet.6b00391
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C34 H29 Cl2 N3 Pd'
_chemical_formula_sum            'C34 H29 Cl2 N3 Pd'
_chemical_formula_weight         656.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2016-03-23
_audit_creation_method
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Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
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_cell_angle_alpha                90
_cell_angle_beta                 113.572(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6356(4)
_cell_length_b                   23.0959(5)
_cell_length_c                   12.5597(4)
_cell_measurement_reflns_used    5985
_cell_measurement_theta_max      61.0280
_cell_measurement_theta_min      3.8240
_cell_volume                     3093.59(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, etc., in preparation (2013)'
_diffrn_detector_area_resol_mean 16.0855
_diffrn_measured_fraction_theta_full 0.9898
_diffrn_measured_fraction_theta_max 0.9922
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1321900000
_diffrn_orient_matrix_UB_12      -0.0255317000
_diffrn_orient_matrix_UB_13      0.0329979000
_diffrn_orient_matrix_UB_21      -0.0218995000
_diffrn_orient_matrix_UB_22      -0.0416227000
_diffrn_orient_matrix_UB_23      0.0857883000
_diffrn_orient_matrix_UB_31      -0.0543184000
_diffrn_orient_matrix_UB_32      -0.0454560000
_diffrn_orient_matrix_UB_33      -0.0972037000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15395
_diffrn_reflns_theta_full        61.0427
_diffrn_reflns_theta_max         61.04
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.4104
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1342.6738
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         2.3003
_refine_diff_density_min         -1.9037
_refine_diff_density_rms         0.1754
_refine_ls_d_res_high            0.8810
_refine_ls_d_res_low             11.5480
_refine_ls_goodness_of_fit_ref   1.0516
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    54
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0516
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0693
_refine_ls_shift/su_max          0.0076
_refine_ls_shift/su_mean         0.0006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1295P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1870
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -13
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -6
_reflns_number_gt                4011
_reflns_number_total             4700
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            om6b00391_si_002.cif
_cod_data_source_block           c4
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               4088761
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 98.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
2.b Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C28(H28a,H28b,H28c)
;