#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:41:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178529 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/34/4063478.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_4063478
loop_
_publ_author_name
'Chan, Kai-Ting'
'Tsai, Yi-Hua'
'Lin, Wu-Shien'
'Wu, Jia-Rong'
'Chen, Shih-Jung'
'Liao, Fu-Xing'
'Hu, Ching-Han'
'Lee, Hon Man'
_publ_section_title
;
 Palladium Complexes with Carbene and Phosphine Ligands: Synthesis,
 Structural Characterization, and Direct Arylation Reactions between Aryl
 Halides and Alkynes
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              463
_journal_page_last               472
_journal_paper_doi               10.1021/om9009203
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C22 H21 Cl2 N3 Pd'
_chemical_formula_sum            'C22 H21 Cl2 N3 Pd'
_chemical_formula_weight         504.72
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 111.7780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0547(7)
_cell_length_b                   25.3595(18)
_cell_length_c                   9.7807(7)
_cell_measurement_reflns_used    5956
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.8
_cell_volume                     2085.6(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21093
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.61
_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    1.159
_exptl_absorpt_correction_T_max  0.9551
_exptl_absorpt_correction_T_min  0.7765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0219
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0308P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0544
_refine_ls_wR_factor_ref         0.0572
_reflns_number_gt                3699
_reflns_number_total             4338
_reflns_threshold_expression     I>2σ
_cod_data_source_file            om9009203_si_001.cif
_cod_data_source_block           7
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4063478
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5064(2) 0.10885(7) 0.9051(2) 0.0191(4) Uani 1 1 d . . .
C2 C 0.7092(3) 0.08547(8) 0.8384(2) 0.0264(5) Uani 1 1 d . . .
H2 H 0.7773 0.0836 0.7844 0.032 Uiso 1 1 calc R . .
C3 C 0.7268(3) 0.05918(8) 0.9620(2) 0.0251(5) Uani 1 1 d . . .
H3 H 0.8099 0.0353 1.0130 0.030 Uiso 1 1 calc R . .
C4 C 0.5065(3) 0.14837(8) 0.6697(2) 0.0258(5) Uani 1 1 d . . .
H4A H 0.5943 0.1619 0.6422 0.031 Uiso 1 1 calc R . .
H4B H 0.4509 0.1791 0.6909 0.031 Uiso 1 1 calc R . .
C5 C 0.3914(3) 0.11805(8) 0.5412(2) 0.0242(5) Uani 1 1 d . . .
C6 C 0.4447(3) 0.07704(9) 0.4776(2) 0.0287(5) Uani 1 1 d . . .
H6 H 0.5541 0.0677 0.5164 0.034 Uiso 1 1 calc R . .
C7 C 0.3414(3) 0.04959(9) 0.3592(3) 0.0355(6) Uani 1 1 d . . .
H7 H 0.3797 0.0213 0.3177 0.043 Uiso 1 1 calc R . .
C8 C 0.1830(3) 0.06303(10) 0.3008(3) 0.0381(6) Uani 1 1 d . . .
H8 H 0.1120 0.0443 0.2184 0.046 Uiso 1 1 calc R . .
C9 C 0.1275(3) 0.10373(11) 0.3620(3) 0.0399(6) Uani 1 1 d . . .
H9 H 0.0183 0.1132 0.3217 0.048 Uiso 1 1 calc R . .
C10 C 0.2313(3) 0.13098(9) 0.4829(3) 0.0328(6) Uani 1 1 d . . .
H10 H 0.1922 0.1586 0.5258 0.039 Uiso 1 1 calc R . .
C11 C 0.5737(3) 0.05224(8) 1.1298(2) 0.0228(4) Uani 1 1 d . . .
H11A H 0.5870 0.0135 1.1313 0.027 Uiso 1 1 calc R . .
H11B H 0.4627 0.0597 1.1195 0.027 Uiso 1 1 calc R . .
C12 C 0.6847(2) 0.07449(7) 1.2745(2) 0.0197(4) Uani 1 1 d . . .
C13 C 0.7759(2) 0.04049(8) 1.3844(2) 0.0223(4) Uani 1 1 d . . .
H13 H 0.7726 0.0036 1.3662 0.027 Uiso 1 1 calc R . .
C14 C 0.8720(3) 0.06012(8) 1.5210(2) 0.0243(5) Uani 1 1 d . . .
H14 H 0.9350 0.0368 1.5959 0.029 Uiso 1 1 calc R . .
C15 C 0.8758(3) 0.11387(8) 1.5478(2) 0.0254(5) Uani 1 1 d . . .
H15 H 0.9409 0.1273 1.6415 0.031 Uiso 1 1 calc R . .
C16 C 0.7850(3) 0.14796(8) 1.4384(3) 0.0283(5) Uani 1 1 d . . .
H16 H 0.7878 0.1848 1.4570 0.034 Uiso 1 1 calc R . .
C17 C 0.6900(3) 0.12837(8) 1.3019(2) 0.0249(5) Uani 1 1 d . . .
H17 H 0.6282 0.1518 1.2267 0.030 Uiso 1 1 calc R . .
C18 C 0.0496(3) 0.17372(9) 1.0120(3) 0.0344(6) Uani 1 1 d . . .
H18 H 0.0949 0.1466 1.0820 0.041 Uiso 1 1 calc R . .
C19 C -0.0875(3) 0.19856(10) 1.0097(3) 0.0444(7) Uani 1 1 d . . .
H19 H -0.1345 0.1888 1.0781 0.053 Uiso 1 1 calc R . .
C20 C -0.1552(3) 0.23746(10) 0.9076(3) 0.0423(7) Uani 1 1 d . . .
H20 H -0.2503 0.2545 0.9033 0.051 Uiso 1 1 calc R . .
C21 C -0.0828(3) 0.25121(9) 0.8120(3) 0.0412(6) Uani 1 1 d . . .
H21 H -0.1271 0.2779 0.7403 0.049 Uiso 1 1 calc R . .
C22 C 0.0560(3) 0.22561(8) 0.8214(3) 0.0292(5) Uani 1 1 d . . .
H22 H 0.1072 0.2360 0.7567 0.035 Uiso 1 1 calc R . .
Cl1 Cl 0.17795(6) 0.068212(19) 0.87959(6) 0.02643(12) Uani 1 1 d . . .
Cl2 Cl 0.46442(6) 0.223207(19) 0.95501(6) 0.02764(13) Uani 1 1 d . . .
N1 N 0.5998(2) 0.07365(6) 1.00129(18) 0.0208(4) Uani 1 1 d . . .
N2 N 0.5738(2) 0.11588(6) 0.80368(18) 0.0213(4) Uani 1 1 d . . .
N3 N 0.1203(2) 0.18702(6) 0.91780(19) 0.0218(4) Uani 1 1 d . . .
Pd1 Pd 0.319129(18) 0.146076(6) 0.913187(16) 0.01844(6) Uani 1 1 d . . .
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'
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
N1 C1 N2 105.25(16) . . ?
N1 C1 Pd1 128.16(13) . . ?
N2 C1 Pd1 126.49(15) . . ?
C3 C2 N2 107.33(17) . . ?
C3 C2 H2 126.3 . . ?
N2 C2 H2 126.3 . . ?
C2 C3 N1 106.54(19) . . ?
C2 C3 H3 126.7 . . ?
N1 C3 H3 126.7 . . ?
N2 C4 C5 112.62(17) . . ?
N2 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
N2 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C10 C5 C6 118.6(2) . . ?
C10 C5 C4 121.00(19) . . ?
C6 C5 C4 120.4(2) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 120.4(2) . . ?
C5 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
N1 C11 C12 113.71(16) . . ?
N1 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N1 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C17 119.6(2) . . ?
C13 C12 C11 119.52(18) . . ?
C17 C12 C11 120.78(19) . . ?
C12 C13 C14 120.24(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
N3 C18 C19 121.7(2) . . ?
N3 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 118.7(2) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 119.1(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
N3 C22 C21 122.5(2) . . ?
N3 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
C1 N1 C3 110.60(16) . . ?
C1 N1 C11 125.90(16) . . ?
C3 N1 C11 123.50(17) . . ?
C1 N2 C2 110.27(16) . . ?
C1 N2 C4 125.08(17) . . ?
C2 N2 C4 124.52(16) . . ?
C22 N3 C18 118.30(18) . . ?
C22 N3 Pd1 120.15(13) . . ?
C18 N3 Pd1 121.47(15) . . ?
C1 Pd1 N3 178.55(7) . . ?
C1 Pd1 Cl2 88.32(6) . . ?
N3 Pd1 Cl2 90.80(5) . . ?
C1 Pd1 Cl1 91.37(6) . . ?
N3 Pd1 Cl1 89.55(5) . . ?
Cl2 Pd1 Cl1 178.08(2) . . ?
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
C1 N1 1.344(2) . ?
C1 N2 1.355(2) . ?
C1 Pd1 1.9682(18) . ?
C2 C3 1.338(3) . ?
C2 N2 1.380(3) . ?
C2 H2 0.9500 . ?
C3 N1 1.390(2) . ?
C3 H3 0.9500 . ?
C4 N2 1.475(3) . ?
C4 C5 1.512(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.385(3) . ?
C5 C6 1.387(3) . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 N1 1.467(2) . ?
C11 C12 1.509(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.386(3) . ?
C12 C17 1.390(3) . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 N3 1.346(2) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.371(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 N3 1.333(3) . ?
C22 H22 0.9500 . ?
Cl1 Pd1 2.3086(5) . ?
Cl2 Pd1 2.3075(5) . ?
N3 Pd1 2.0932(16) . ?
