# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2006

data_global

_journal_coden_Cambridge         440

loop_
_publ_author_name
'Gang Zou'
'Wen Huang'
'Jie Tang'
'Yuanjing Xiao'

_publ_contact_author_name        'Gang Zou'
_publ_contact_author_address     
;
Chemistry
East china normal university
3663 North Zhongshan Rd.
Shanghai
200062
CHINA
;

_publ_contact_author_email       GNGZOU@YAHOO.COM.CN

_publ_requested_journal          'New Journal of Chemistry'

_publ_section_title              
;
Heck reaction catalysed by palladium supported with an
electron-rich benzimidazolylidene generated in situ: Remarkable ligand
electronic effects and controllable mono- and di-arylation
;

# Attachment 'B601833E_cif.txt'

data_cd25134
_database_code_depnum_ccdc_archive 'CCDC 600971'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H44 Cl2 N4 Pd'
_chemical_formula_weight         637.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.0750(13)
_cell_length_b                   8.8410(8)
_cell_length_c                   14.3377(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.0520(10)
_cell_angle_gamma                90.00
_cell_volume                     1559.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2192
_cell_measurement_theta_min      5.642
_cell_measurement_theta_max      50.789

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.59641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8978
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         26.99
_reflns_number_total             3407
_reflns_number_gt                2348
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1583P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3407
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2252
_refine_ls_wR_factor_gt          0.2101
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd 0.5000 0.5000 0.5000 0.0408(3) Uani 1 2 d S . .
Cl Cl 0.48871(9) 0.23517(14) 0.49525(8) 0.0442(3) Uani 1 1 d . . .
N1 N 0.5778(4) 0.5200(4) 0.3351(4) 0.0428(10) Uani 1 1 d . . .
N2 N 0.7033(3) 0.4392(5) 0.4876(3) 0.0472(9) Uani 1 1 d . . .
C1 C 0.6012(4) 0.4877(4) 0.4376(4) 0.0422(11) Uani 1 1 d . . .
C2 C 0.6667(5) 0.4919(4) 0.3219(5) 0.0444(12) Uani 1 1 d . . .
C3 C 0.6877(6) 0.5060(5) 0.2378(6) 0.0605(16) Uani 1 1 d . . .
H3 H 0.6338 0.5411 0.1721 0.073 Uiso 1 1 calc R . .
C4 C 0.7822(7) 0.4706(7) 0.2500(7) 0.0730(19) Uani 1 1 d . . .
H4 H 0.7946 0.4791 0.1921 0.088 Uiso 1 1 calc R . .
C5 C 0.8685(5) 0.4186(7) 0.3502(6) 0.0724(17) Uani 1 1 d . . .
H5 H 0.9358 0.3949 0.3569 0.087 Uiso 1 1 calc R . .
C6 C 0.8516(4) 0.4038(6) 0.4366(5) 0.0615(14) Uani 1 1 d . . .
H6 H 0.9063 0.3706 0.5024 0.074 Uiso 1 1 calc R . .
C7 C 0.7486(4) 0.4409(6) 0.4207(4) 0.0465(11) Uani 1 1 d . . .
C8 C 0.4725(4) 0.5739(6) 0.2503(4) 0.0471(11) Uani 1 1 d . . .
H8A H 0.4843 0.6418 0.2038 0.057 Uiso 1 1 calc R . .
H8B H 0.4362 0.6303 0.2819 0.057 Uiso 1 1 calc R . .
C9 C 0.4005(4) 0.4456(6) 0.1852(4) 0.0477(11) Uani 1 1 d . . .
H9A H 0.3801 0.3861 0.2295 0.057 Uiso 1 1 calc R . .
H9B H 0.4410 0.3804 0.1626 0.057 Uiso 1 1 calc R . .
C10 C 0.2977(5) 0.4996(5) 0.0869(6) 0.0586(16) Uani 1 1 d . . .
H10A H 0.2573 0.5651 0.1093 0.070 Uiso 1 1 calc R . .
H10B H 0.3180 0.5587 0.0423 0.070 Uiso 1 1 calc R . .
C11 C 0.2263(5) 0.3726(8) 0.0227(6) 0.089(2) Uani 1 1 d . . .
H11A H 0.2651 0.3090 -0.0016 0.123 Uiso 1 1 calc R . .
H11B H 0.1627 0.4126 -0.0376 0.123 Uiso 1 1 calc R . .
H11C H 0.2050 0.3145 0.0661 0.123 Uiso 1 1 calc R . .
C12 C 0.7631(5) 0.3981(7) 0.6002(4) 0.0645(15) Uani 1 1 d . . .
H12A H 0.8122 0.3153 0.6098 0.077 Uiso 1 1 calc R . .
H12B H 0.7125 0.3644 0.6237 0.077 Uiso 1 1 calc R . .
C13 C 0.8295(7) 0.5366(9) 0.6691(6) 0.083(2) Uani 1 1 d . . .
H13A H 0.8688 0.5814 0.6361 0.099 Uiso 1 1 calc R . .
H13B H 0.7789 0.6119 0.6681 0.099 Uiso 1 1 calc R . .
C14 C 0.9105(8) 0.4992(7) 0.7851(8) 0.091(3) Uani 1 1 d . . .
H14A H 0.8724 0.4493 0.8176 0.109 Uiso 1 1 calc R . .
H14B H 0.9645 0.4293 0.7869 0.109 Uiso 1 1 calc R . .
C15 C 0.9632(8) 0.6288(9) 0.8449(7) 0.121(3) Uani 1 1 d . . .
H15A H 1.0066 0.6731 0.8172 0.132 Uiso 1 1 calc R . .
H15B H 1.0090 0.6010 0.9182 0.132 Uiso 1 1 calc R . .
H15C H 0.9099 0.7007 0.8402 0.132 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pd 0.0398(4) 0.0445(4) 0.0328(4) -0.00227(18) 0.0134(3) -0.00242(18)
Cl 0.0613(7) 0.0310(6) 0.0467(7) -0.0068(4) 0.0314(6) -0.0073(4)
N1 0.046(2) 0.046(2) 0.032(2) 0.0019(15) 0.0148(19) -0.0013(16)
N2 0.046(2) 0.052(2) 0.039(2) 0.0035(19) 0.0168(19) -0.0014(19)
C1 0.046(3) 0.041(3) 0.035(3) -0.0025(17) 0.015(2) -0.0035(18)
C2 0.052(3) 0.036(3) 0.041(3) -0.0040(18) 0.020(2) -0.0025(18)
C3 0.075(4) 0.062(4) 0.047(4) -0.001(2) 0.031(3) 0.003(2)
C4 0.081(5) 0.088(5) 0.068(5) -0.014(3) 0.050(4) -0.014(4)
C5 0.071(4) 0.073(4) 0.091(5) -0.009(4) 0.053(4) 0.000(3)
C6 0.050(3) 0.060(3) 0.073(4) -0.001(3) 0.029(3) 0.000(2)
C7 0.050(3) 0.042(3) 0.047(3) -0.001(2) 0.023(2) -0.002(2)
C8 0.053(3) 0.040(3) 0.044(3) 0.002(2) 0.020(2) 0.006(2)
C9 0.049(3) 0.044(3) 0.039(3) -0.002(2) 0.012(2) 0.003(2)
C10 0.053(3) 0.053(3) 0.052(4) 0.001(2) 0.011(3) 0.003(2)
C11 0.060(4) 0.093(5) 0.078(5) -0.013(4) 0.006(3) -0.002(3)
C12 0.052(3) 0.084(4) 0.043(3) 0.012(3) 0.012(3) 0.004(3)
C13 0.088(5) 0.100(5) 0.058(4) 0.006(4) 0.034(4) 0.000(4)
C14 0.087(6) 0.101(7) 0.071(6) -0.003(3) 0.026(5) -0.006(4)
C15 0.121(7) 0.119(7) 0.103(7) -0.039(5) 0.039(6) -0.037(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd C1 2.020(6) 3_666 ?
Pd C1 2.020(6) . ?
Pd Cl 2.3455(13) 3_666 ?
Pd Cl 2.3455(13) . ?
N1 C1 1.370(7) . ?
N1 C2 1.377(7) . ?
N1 C8 1.467(6) . ?
N2 C1 1.327(6) . ?
N2 C7 1.386(6) . ?
N2 C12 1.457(6) . ?
C2 C3 1.380(9) . ?
C2 C7 1.398(7) . ?
C3 C4 1.292(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.434(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(7) . ?
C6 H6 0.9300 . ?
C8 C9 1.506(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.525(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.489(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.566(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.528(12) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.408(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Pd C1 180.000(1) 3_666 . ?
C1 Pd Cl 89.19(11) 3_666 3_666 ?
C1 Pd Cl 90.81(11) . 3_666 ?
C1 Pd Cl 90.81(11) 3_666 . ?
C1 Pd Cl 89.19(11) . . ?
Cl Pd Cl 180.0 3_666 . ?
C1 N1 C2 110.4(5) . . ?
C1 N1 C8 125.2(5) . . ?
C2 N1 C8 124.4(4) . . ?
C1 N2 C7 111.3(4) . . ?
C1 N2 C12 124.8(5) . . ?
C7 N2 C12 123.8(4) . . ?
N2 C1 N1 106.4(5) . . ?
N2 C1 Pd 126.0(4) . . ?
N1 C1 Pd 127.5(4) . . ?
N1 C2 C3 134.4(6) . . ?
N1 C2 C7 106.0(5) . . ?
C3 C2 C7 119.6(6) . . ?
C4 C3 C2 120.2(7) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.9(7) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 120.0(6) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 116.9(6) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 H6 121.6 . . ?
N2 C7 C6 132.6(5) . . ?
N2 C7 C2 106.0(4) . . ?
C6 C7 C2 121.4(5) . . ?
N1 C8 C9 112.0(4) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 112.8(4) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 112.8(5) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 110.5(5) . . ?
N2 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 114.7(6) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 112.4(7) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C1 N1 0.9(5) . . . . ?
C12 N2 C1 N1 177.3(5) . . . . ?
C7 N2 C1 Pd 178.1(3) . . . . ?
C12 N2 C1 Pd -5.5(7) . . . . ?
C2 N1 C1 N2 -0.3(5) . . . . ?
C8 N1 C1 N2 178.4(4) . . . . ?
C2 N1 C1 Pd -177.5(3) . . . . ?
C8 N1 C1 Pd 1.3(6) . . . . ?
C1 Pd C1 N2 28(100) 3_666 . . . ?
Cl Pd C1 N2 108.6(4) 3_666 . . . ?
Cl Pd C1 N2 -71.4(4) . . . . ?
C1 Pd C1 N1 -155(100) 3_666 . . . ?
Cl Pd C1 N1 -74.8(4) 3_666 . . . ?
Cl Pd C1 N1 105.2(4) . . . . ?
C1 N1 C2 C3 -179.2(5) . . . . ?
C8 N1 C2 C3 2.0(8) . . . . ?
C1 N1 C2 C7 -0.4(5) . . . . ?
C8 N1 C2 C7 -179.1(4) . . . . ?
N1 C2 C3 C4 179.5(5) . . . . ?
C7 C2 C3 C4 0.8(8) . . . . ?
C2 C3 C4 C5 -1.1(9) . . . . ?
C3 C4 C5 C6 0.6(10) . . . . ?
C4 C5 C6 C7 0.2(9) . . . . ?
C1 N2 C7 C6 178.7(5) . . . . ?
C12 N2 C7 C6 2.2(9) . . . . ?
C1 N2 C7 C2 -1.1(6) . . . . ?
C12 N2 C7 C2 -177.6(5) . . . . ?
C5 C6 C7 N2 179.7(6) . . . . ?
C5 C6 C7 C2 -0.5(8) . . . . ?
N1 C2 C7 N2 0.9(5) . . . . ?
C3 C2 C7 N2 179.9(4) . . . . ?
N1 C2 C7 C6 -179.0(5) . . . . ?
C3 C2 C7 C6 0.1(7) . . . . ?
C1 N1 C8 C9 -92.3(5) . . . . ?
C2 N1 C8 C9 86.3(5) . . . . ?
N1 C8 C9 C10 -171.6(5) . . . . ?
C8 C9 C10 C11 -179.7(6) . . . . ?
C1 N2 C12 C13 -93.4(6) . . . . ?
C7 N2 C12 C13 82.5(7) . . . . ?
N2 C12 C13 C14 -169.7(7) . . . . ?
C12 C13 C14 C15 -176.5(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.662
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.180