#------------------------------------------------------------------------------
#$Date: 2016-03-23 04:09:31 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179278 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/98/4319867.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_4319867
loop_
_publ_author_name
'Eric Bosch'
'Charles L. Barnes'
_publ_section_title
;
 1,2-Bis(2-pyridylethynyl)benzene, a Novel Trans-Chelating Bipyridyl
 Ligand. Structural Characterization of the Complexes with Silver(I)
 Triflate and Palladium(II) Chloride
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3097
_journal_page_last               3100
_journal_paper_doi               10.1021/ic010058u
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C20 H12 Cl2 N2 Pd'
_chemical_formula_weight         457.62
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.269(2)
_cell_angle_beta                 87.255(2)
_cell_angle_gamma                70.697(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4297(9)
_cell_length_b                   8.4100(10)
_cell_length_c                   15.1003(18)
_cell_measurement_reflns_used    821
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.6
_cell_volume                     877.64(18)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5462
_diffrn_reflns_theta_full        27.12
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    1.366
_exptl_absorpt_correction_T_max  0.8214
_exptl_absorpt_correction_T_min  0.7264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Data were corrected for decay and absorption using the program SADABS
  based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995).
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0434P)²+0.3693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                3456
_reflns_number_total             3766
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010058u_2.cif
_cod_data_source_block           BDPPd
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4319867
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Pd1 Pd 0.90431(2) 0.966143(19) 0.170197(11) 0.02079(7) Uani 1 1 d . . .
N1 N 0.7831(3) 0.7944(2) 0.14823(12) 0.0221(4) Uani 1 1 d . . .
C1 C 0.8448(3) 0.7019(3) 0.08228(15) 0.0264(5) Uani 1 1 d . . .
H1 H 0.9475 0.7180 0.0461 0.032 Uiso 1 1 calc R . .
Cl2 Cl 1.07081(8) 0.77947(7) 0.29219(4) 0.02752(13) Uani 1 1 d . . .
Cl3 Cl 0.75028(8) 1.14816(7) 0.04348(4) 0.02833(13) Uani 1 1 d . . .
N2 N 1.0255(3) 1.1382(2) 0.19105(13) 0.0230(4) Uani 1 1 d . . .
C2 C 0.7647(4) 0.5838(3) 0.06481(16) 0.0285(5) Uani 1 1 d . . .
H2 H 0.8139 0.5179 0.0185 0.034 Uiso 1 1 calc R . .
C3 C 0.6116(4) 0.5624(3) 0.11576(17) 0.0302(5) Uani 1 1 d . . .
H3 H 0.5529 0.4832 0.1043 0.036 Uiso 1 1 calc R . .
C4 C 0.5458(3) 0.6586(3) 0.18364(17) 0.0299(5) Uani 1 1 d . . .
H4 H 0.4405 0.6467 0.2191 0.036 Uiso 1 1 calc R . .
C5 C 0.6347(3) 0.7727(3) 0.19958(15) 0.0237(4) Uani 1 1 d . . .
C6 C 0.5688(3) 0.8756(3) 0.26847(16) 0.0264(5) Uani 1 1 d . . .
C7 C 0.5008(3) 0.9635(3) 0.32353(15) 0.0252(5) Uani 1 1 d . . .
C8 C 0.4136(3) 1.0796(3) 0.38477(15) 0.0258(5) Uani 1 1 d . . .
C9 C 0.2570(3) 1.0633(3) 0.43580(16) 0.0323(5) Uani 1 1 d . . .
H9 H 0.2105 0.9722 0.4318 0.039 Uiso 1 1 calc R . .
C10 C 0.1696(4) 1.1795(4) 0.49205(18) 0.0396(6) Uani 1 1 d . . .
H10 H 0.0646 1.1666 0.5274 0.047 Uiso 1 1 calc R . .
C11 C 0.2333(4) 1.3140(4) 0.49737(18) 0.0403(6) Uani 1 1 d . . .
H11 H 0.1711 1.3937 0.5359 0.048 Uiso 1 1 calc R . .
C12 C 0.3882(4) 1.3340(3) 0.44657(18) 0.0358(6) Uani 1 1 d . . .
H12 H 0.4305 1.4279 0.4499 0.043 Uiso 1 1 calc R . .
C13 C 0.4811(3) 1.2157(3) 0.39082(15) 0.0265(5) Uani 1 1 d . . .
C14 C 0.6446(3) 1.2313(3) 0.33977(16) 0.0270(5) Uani 1 1 d . . .
C15 C 0.7828(3) 1.2381(3) 0.29713(15) 0.0263(5) Uani 1 1 d . . .
C16 C 0.9488(3) 1.2507(3) 0.24858(15) 0.0236(4) Uani 1 1 d . . .
C17 C 1.0301(3) 1.3731(3) 0.25985(16) 0.0278(5) Uani 1 1 d . . .
H17 H 0.9742 1.4525 0.2994 0.033 Uiso 1 1 calc R . .
C18 C 1.1937(4) 1.3779(3) 0.21272(17) 0.0303(5) Uani 1 1 d . . .
H18 H 1.2502 1.4616 0.2191 0.036 Uiso 1 1 calc R . .
C19 C 1.2737(3) 1.2596(3) 0.15629(17) 0.0298(5) Uani 1 1 d . . .
H19 H 1.3880 1.2586 0.1250 0.036 Uiso 1 1 calc R . .
C20 C 1.1849(3) 1.1432(3) 0.14624(16) 0.0269(5) Uani 1 1 d . . .
H20 H 1.2382 1.0640 0.1063 0.032 Uiso 1 1 calc R . .
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
N2 Pd1 N1 179.53(7) . . ?
N2 Pd1 Cl2 89.85(5) . . ?
N1 Pd1 Cl2 90.52(5) . . ?
N2 Pd1 Cl3 89.96(6) . . ?
N1 Pd1 Cl3 89.66(5) . . ?
Cl2 Pd1 Cl3 177.17(2) . . ?
C1 N1 C5 118.92(19) . . ?
C1 N1 Pd1 120.73(15) . . ?
C5 N1 Pd1 120.34(15) . . ?
N1 C1 C2 122.4(2) . . ?
C20 N2 C16 119.3(2) . . ?
C20 N2 Pd1 119.20(16) . . ?
C16 N2 Pd1 121.52(15) . . ?
C1 C2 C3 119.2(2) . . ?
C4 C3 C2 118.8(2) . . ?
C3 C4 C5 119.6(2) . . ?
N1 C5 C4 121.1(2) . . ?
N1 C5 C6 117.9(2) . . ?
C4 C5 C6 121.0(2) . . ?
C7 C6 C5 175.2(2) . . ?
C6 C7 C8 175.9(2) . . ?
C9 C8 C13 119.6(2) . . ?
C9 C8 C7 120.5(2) . . ?
C13 C8 C7 119.9(2) . . ?
C10 C9 C8 120.0(3) . . ?
C11 C10 C9 120.6(2) . . ?
C10 C11 C12 120.4(2) . . ?
C11 C12 C13 119.8(3) . . ?
C12 C13 C8 119.5(2) . . ?
C12 C13 C14 120.6(2) . . ?
C8 C13 C14 119.9(2) . . ?
C15 C14 C13 177.6(2) . . ?
C14 C15 C16 177.7(2) . . ?
N2 C16 C17 120.9(2) . . ?
N2 C16 C15 117.7(2) . . ?
C17 C16 C15 121.3(2) . . ?
C18 C17 C16 119.3(2) . . ?
C19 C18 C17 119.3(2) . . ?
C20 C19 C18 119.0(2) . . ?
N2 C20 C19 122.2(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
Pd1 N2 2.0113(19) . ?
Pd1 N1 2.0143(18) . ?
Pd1 Cl2 2.3119(6) . ?
Pd1 Cl3 2.3185(6) . ?
N1 C1 1.338(3) . ?
N1 C5 1.361(3) . ?
C1 C2 1.380(3) . ?
N2 C20 1.345(3) . ?
N2 C16 1.360(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.384(4) . ?
C4 C5 1.388(3) . ?
C5 C6 1.430(3) . ?
C6 C7 1.189(3) . ?
C7 C8 1.435(3) . ?
C8 C9 1.397(3) . ?
C8 C13 1.410(3) . ?
C9 C10 1.381(4) . ?
C10 C11 1.378(4) . ?
C11 C12 1.394(4) . ?
C12 C13 1.396(3) . ?
C13 C14 1.438(3) . ?
C14 C15 1.198(3) . ?
C15 C16 1.430(3) . ?
C16 C17 1.391(3) . ?
C17 C18 1.388(3) . ?
C18 C19 1.384(4) . ?
C19 C20 1.380(3) . ?
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
N2 Pd1 N1 C1 40(9) . . . . ?
Cl2 Pd1 N1 C1 -102.68(17) . . . . ?
Cl3 Pd1 N1 C1 74.49(17) . . . . ?
N2 Pd1 N1 C5 -139(9) . . . . ?
Cl2 Pd1 N1 C5 78.34(16) . . . . ?
Cl3 Pd1 N1 C5 -104.49(16) . . . . ?
C5 N1 C1 C2 -0.6(3) . . . . ?
Pd1 N1 C1 C2 -179.62(17) . . . . ?
N1 Pd1 N2 C20 -48(9) . . . . ?
Cl2 Pd1 N2 C20 94.06(17) . . . . ?
Cl3 Pd1 N2 C20 -83.11(17) . . . . ?
N1 Pd1 N2 C16 131(9) . . . . ?
Cl2 Pd1 N2 C16 -86.72(16) . . . . ?
Cl3 Pd1 N2 C16 96.11(16) . . . . ?
N1 C1 C2 C3 1.6(4) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C1 N1 C5 C4 -0.9(3) . . . . ?
Pd1 N1 C5 C4 178.07(17) . . . . ?
C1 N1 C5 C6 -178.8(2) . . . . ?
Pd1 N1 C5 C6 0.2(3) . . . . ?
C3 C4 C5 N1 1.5(4) . . . . ?
C3 C4 C5 C6 179.2(2) . . . . ?
N1 C5 C6 C7 133(3) . . . . ?
C4 C5 C6 C7 -45(3) . . . . ?
C5 C6 C7 C8 -62(5) . . . . ?
C6 C7 C8 C9 111(3) . . . . ?
C6 C7 C8 C13 -66(3) . . . . ?
C13 C8 C9 C10 -0.3(4) . . . . ?
C7 C8 C9 C10 -177.6(2) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 C8 1.7(4) . . . . ?
C11 C12 C13 C14 -178.2(2) . . . . ?
C9 C8 C13 C12 -1.1(3) . . . . ?
C7 C8 C13 C12 176.2(2) . . . . ?
C9 C8 C13 C14 178.8(2) . . . . ?
C7 C8 C13 C14 -3.9(3) . . . . ?
C12 C13 C14 C15 157(6) . . . . ?
C8 C13 C14 C15 -23(6) . . . . ?
C13 C14 C15 C16 -138(6) . . . . ?
C20 N2 C16 C17 1.6(3) . . . . ?
Pd1 N2 C16 C17 -177.59(16) . . . . ?
C20 N2 C16 C15 -178.1(2) . . . . ?
Pd1 N2 C16 C15 2.7(3) . . . . ?
C14 C15 C16 N2 166(6) . . . . ?
C14 C15 C16 C17 -13(6) . . . . ?
N2 C16 C17 C18 -1.1(3) . . . . ?
C15 C16 C17 C18 178.6(2) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C17 C18 C19 C20 2.0(4) . . . . ?
C16 N2 C20 C19 -0.3(3) . . . . ?
Pd1 N2 C20 C19 178.98(18) . . . . ?
C18 C19 C20 N2 -1.6(4) . . . . ?
