#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:19:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178559 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/67/4066794.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4066794
loop_
_publ_author_name
'Lee, Jhen-Yi'
'Cheng, Pi-Yun'
'Tsai, Yi-Hua'
'Lin, Guan-Ru'
'Liu, Shih-Pu'
'Sie, Ming-Han'
'Lee, Hon Man'
_publ_section_title
;
 Efficient Heck Reactions Catalyzed by Palladium(0) and -(II) Complexes
 Bearing N-Heterocyclic Carbene and Amide Functionalities
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              3901
_journal_paper_doi               10.1021/om1006402
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C44 H36 N6 O2 Pd'
_chemical_formula_sum            'C44 H36 N6 O2 Pd'
_chemical_formula_weight         787.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.090(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.4007(19)
_cell_length_b                   16.954(3)
_cell_length_c                   9.7297(15)
_cell_measurement_temperature    150(2)
_cell_volume                     1777.2(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 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_sigmaI/netI    0.0860
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16521
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.89
_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    0.571
_exptl_absorpt_correction_T_max  0.9347
_exptl_absorpt_correction_T_min  0.8944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.284
_refine_diff_density_min         -3.085
_refine_diff_density_rms         0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1376P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1734
_refine_ls_wR_factor_ref         0.2373
_reflns_number_gt                2002
_reflns_number_total             3531
_reflns_threshold_expression     I>2σ
_cod_data_source_file            om1006402_si_002.cif
_cod_data_source_block           4a
_cod_original_cell_volume        1777.3(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4066794
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'
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
C1 C 0.5475(6) 1.0203(4) 0.8220(8) 0.0234(15) Uani 1 1 d .
C2 C 0.6007(8) 1.0992(4) 0.6631(9) 0.041(2) Uani 1 1 d .
H2 H 0.6136 1.1453 0.6144 0.049 Uiso 1 1 calc R
C3 C 0.6212(8) 1.0255(4) 0.6328(10) 0.045(2) Uani 1 1 d .
H3 H 0.6517 1.0086 0.5577 0.054 Uiso 1 1 calc R
C4 C 0.5965(7) 0.8892(4) 0.7340(10) 0.038(2) Uani 1 1 d .
H4A H 0.5232 0.8677 0.6573 0.045 Uiso 1 1 calc R
H4B H 0.5943 0.8696 0.8290 0.045 Uiso 1 1 calc R
C5 C 0.7111(7) 0.8601(4) 0.7100(9) 0.0346(18) Uani 1 1 d .
C6 C 0.7063(10) 0.8206(4) 0.5868(11) 0.055(3) Uani 1 1 d .
H6 H 0.6290 0.8127 0.5123 0.066 Uiso 1 1 calc R
C7 C 0.8187(13) 0.7911(5) 0.5699(14) 0.076(4) Uani 1 1 d .
H7 H 0.8159 0.7642 0.4832 0.091 Uiso 1 1 calc R
C8 C 0.9310(11) 0.8014(5) 0.6790(15) 0.079(4) Uani 1 1 d .
H8 H 1.0047 0.7811 0.6671 0.095 Uiso 1 1 calc R
C9 C 0.9370(9) 0.8404(4) 0.8029(13) 0.059(3) Uani 1 1 d .
C10 C 0.8286(7) 0.8712(4) 0.8251(9) 0.0369(19) Uani 1 1 d .
C11 C 0.8411(9) 0.9099(5) 0.9572(12) 0.060(3) Uani 1 1 d .
H11 H 0.7694 0.9314 0.9725 0.072 Uiso 1 1 calc R
C12 C 0.9525(11) 0.9173(6) 1.0629(15) 0.084(4) Uani 1 1 d .
H12 H 0.9573 0.9444 1.1501 0.101 Uiso 1 1 calc R
C13 C 1.0611(10) 0.8858(7) 1.0464(15) 0.077(3) Uani 1 1 d .
H13 H 1.1387 0.8897 1.1221 0.092 Uiso 1 1 calc R
C14 C 1.0514(11) 0.8500(6) 0.9194(17) 0.084(4) Uani 1 1 d .
H14 H 1.1249 0.8300 0.9065 0.101 Uiso 1 1 calc R
C15 C 0.5226(8) 1.1625(4) 0.8563(9) 0.038(2) Uani 1 1 d .
H15A H 0.4329 1.1596 0.8438 0.046 Uiso 1 1 calc R
H15B H 0.5375 1.2123 0.8116 0.046 Uiso 1 1 calc R
C16 C 0.5970(7) 1.1634(4) 1.0189(9) 0.0354(18) Uani 1 1 d .
C17 C 0.6953(7) 1.0850(4) 1.2322(10) 0.038(2) Uani 1 1 d .
C18 C 0.7331(9) 1.1448(5) 1.3369(11) 0.050(2) Uani 1 1 d .
H18 H 0.7024 1.1969 1.3139 0.060 Uiso 1 1 calc R
C19 C 0.8142(10) 1.1281(5) 1.4722(13) 0.066(3) Uani 1 1 d .
H19 H 0.8369 1.1695 1.5416 0.079 Uiso 1 1 calc R
C20 C 0.8643(9) 1.0549(6) 1.5129(12) 0.060(3) Uani 1 1 d .
H20 H 0.9214 1.0456 1.6074 0.072 Uiso 1 1 calc R
C21 C 0.8281(8) 0.9944(5) 1.4099(11) 0.048(2) Uani 1 1 d .
H21 H 0.8608 0.9428 1.4343 0.057 Uiso 1 1 calc R
C22 C 0.7455(8) 1.0091(4) 1.2737(10) 0.039(2) Uani 1 1 d .
H22 H 0.7216 0.9670 1.2056 0.047 Uiso 1 1 calc R
N1 N 0.5892(6) 0.9764(3) 0.7322(8) 0.0378(18) Uani 1 1 d .
N2 N 0.5564(6) 1.0958(3) 0.7814(7) 0.0358(16) Uani 1 1 d .
N3 N 0.6105(6) 1.0941(3) 1.0883(8) 0.0364(16) Uani 1 1 d .
O1 O 0.6394(6) 1.2284(3) 1.0715(7) 0.0558(17) Uani 1 1 d .
Pd1 Pd 0.5000 1.0000 1.0000 0.0327(3) Uani 1 2 d S
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'
O O 0.0106 0.0060 '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'
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
N1 C1 N2 105.0(6) . .
N1 C1 Pd1 135.8(5) . .
N2 C1 Pd1 118.8(5) . .
C3 C2 N2 106.4(6) . .
C3 C2 H2 126.8 . .
N2 C2 H2 126.8 . .
C2 C3 N1 107.5(7) . .
C2 C3 H3 126.2 . .
N1 C3 H3 126.2 . .
N1 C4 C5 112.3(6) . .
N1 C4 H4A 109.1 . .
C5 C4 H4A 109.1 . .
N1 C4 H4B 109.1 . .
C5 C4 H4B 109.1 . .
H4A C4 H4B 107.9 . .
C6 C5 C10 120.4(7) . .
C6 C5 C4 121.3(8) . .
C10 C5 C4 118.2(7) . .
C5 C6 C7 119.6(10) . .
C5 C6 H6 120.2 . .
C7 C6 H6 120.2 . .
C8 C7 C6 120.3(9) . .
C8 C7 H7 119.8 . .
C6 C7 H7 119.8 . .
C9 C8 C7 120.7(9) . .
C9 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
C8 C9 C10 121.3(11) . .
C8 C9 C14 121.9(10) . .
C10 C9 C14 116.8(10) . .
C11 C10 C9 118.4(9) . .
C11 C10 C5 123.9(7) . .
C9 C10 C5 117.6(8) . .
C12 C11 C10 121.8(9) . .
C12 C11 H11 119.1 . .
C10 C11 H11 119.1 . .
C11 C12 C13 121.4(12) . .
C11 C12 H12 119.3 . .
C13 C12 H12 119.3 . .
C14 C13 C12 117.6(12) . .
C14 C13 H13 121.2 . .
C12 C13 H13 121.2 . .
C13 C14 C9 124.0(10) . .
C13 C14 H14 118.0 . .
C9 C14 H14 118.0 . .
N2 C15 C16 112.0(6) . .
N2 C15 H15A 109.2 . .
C16 C15 H15A 109.2 . .
N2 C15 H15B 109.2 . .
C16 C15 H15B 109.2 . .
H15A C15 H15B 107.9 . .
O1 C16 N3 127.2(8) . .
O1 C16 C15 116.3(6) . .
N3 C16 C15 116.5(6) . .
C18 C17 C22 116.9(8) . .
C18 C17 N3 125.7(7) . .
C22 C17 N3 117.4(7) . .
C19 C18 C17 120.0(8) . .
C19 C18 H18 120.0 . .
C17 C18 H18 120.0 . .
C18 C19 C20 123.5(10) . .
C18 C19 H19 118.2 . .
C20 C19 H19 118.2 . .
C19 C20 C21 117.4(10) . .
C19 C20 H20 121.3 . .
C21 C20 H20 121.3 . .
C22 C21 C20 120.5(8) . .
C22 C21 H21 119.7 . .
C20 C21 H21 119.7 . .
C21 C22 C17 121.7(8) . .
C21 C22 H22 119.1 . .
C17 C22 H22 119.1 . .
C1 N1 C3 110.1(6) . .
C1 N1 C4 125.1(6) . .
C3 N1 C4 124.8(6) . .
C1 N2 C2 111.1(5) . .
C1 N2 C15 121.9(6) . .
C2 N2 C15 127.0(5) . .
C16 N3 C17 121.3(6) . .
C16 N3 Pd1 121.4(6) . .
C17 N3 Pd1 117.1(4) . .
C1 Pd1 C1 179.998(3) 3_677 .
C1 Pd1 N3 85.7(2) 3_677 3_677
C1 Pd1 N3 94.3(2) . 3_677
C1 Pd1 N3 94.3(2) 3_677 .
C1 Pd1 N3 85.7(2) . .
N3 Pd1 N3 180.0(4) 3_677 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.347(9) .
C1 N2 1.353(8) .
C1 Pd1 2.006(7) .
C2 C3 1.322(10) .
C2 N2 1.402(9) .
C2 H2 0.9500 .
C3 N1 1.412(10) .
C3 H3 0.9500 .
C4 N1 1.480(8) .
C4 C5 1.484(10) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.358(11) .
C5 C10 1.450(11) .
C6 C7 1.435(14) .
C6 H6 0.9500 .
C7 C8 1.381(15) .
C7 H7 0.9500 .
C8 C9 1.356(15) .
C8 H8 0.9500 .
C9 C10 1.423(10) .
C9 C14 1.430(16) .
C10 C11 1.408(12) .
C11 C12 1.354(14) .
C11 H11 0.9500 .
C12 C13 1.405(16) .
C12 H12 0.9500 .
C13 C14 1.349(16) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 N2 1.464(8) .
C15 C16 1.531(11) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 O1 1.244(8) .
C16 N3 1.339(9) .
C17 C18 1.402(11) .
C17 C22 1.413(9) .
C17 N3 1.426(10) .
C18 C19 1.368(14) .
C18 H18 0.9500 .
C19 C20 1.370(13) .
C19 H19 0.9500 .
C20 C21 1.399(13) .
C20 H20 0.9500 .
C21 C22 1.374(14) .
C21 H21 0.9500 .
C22 H22 0.9500 .
N3 Pd1 2.040(6) .
Pd1 C1 2.006(7) 3_677
Pd1 N3 2.040(6) 3_677
