#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/56/2215623.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2215623
loop_
_publ_author_name
'Zhang-Jie Huang'
'Lin Du'
'Ming-Jin Xie'
'Jing Chen'
_publ_section_title
Dichlorido[bis(2-hexylsulfanyl)-1H-benzimidazole-κN³]palladium(II)
_journal_coeditor_code           OM2153
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2474
_journal_page_last               m2474
_journal_paper_doi               10.1107/S1600536807042584
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Pd Cl2 (C13 H18 N2 S)2]'
_chemical_formula_sum            'C26 H36 Cl2 N4 Pd S2'
_chemical_formula_weight         646.01
_chemical_name_systematic
;
Dichlorido[bis(2-hexylsulfanyl)-1H-benzimidazole-
κN³]palladium(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 113.0730(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.3559(11)
_cell_length_b                   7.7688(6)
_cell_length_c                   14.5566(11)
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      1.54
_cell_volume                     1493.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97) (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker APEXII 1K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12251
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_T_max  0.9016
_exptl_absorpt_correction_T_min  0.8310
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.332
_refine_diff_density_min         -0.528
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0452
_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)+(0.0906P)²+0.5462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                2649
_reflns_number_total             3515
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2153.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215623
_cod_database_fobs_code          2215623
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Pd Pd1 0.0000 0.5000 0.0000 0.04347(15) Uani d S 1
S S1 0.13339(9) 0.4562(2) 0.25428(8) 0.0802(4) Uani d . 1
N N1 -0.0520(3) 0.4856(3) 0.1094(2) 0.0491(7) Uani d . 1
N N2 -0.0570(3) 0.4476(5) 0.2582(2) 0.0706(9) Uani d . 1
H H2A -0.0367 0.4326 0.3216 0.085 Uiso calc R 1
Cl Cl1 0.02540(13) 0.78914(15) 0.02260(10) 0.1020(5) Uani d . 1
C C1 -0.2480(4) 0.4513(7) 0.2038(4) 0.0920(15) Uani d . 1
H H1 -0.2502 0.4356 0.2662 0.110 Uiso calc R 1
C C2 -0.3343(5) 0.4676(8) 0.1192(5) 0.1021(19) Uani d . 1
H H2 -0.3967 0.4647 0.1247 0.123 Uiso calc R 1
C C3 -0.3320(5) 0.4884(6) 0.0248(5) 0.0931(18) Uani d . 1
H H3 -0.3925 0.4974 -0.0309 0.112 Uiso calc R 1
C C4 -0.2417(4) 0.4958(4) 0.0129(4) 0.0712(12) Uani d . 1
H H4 -0.2399 0.5098 -0.0499 0.085 Uiso calc R 1
C C5 -0.1532(3) 0.4818(4) 0.0980(3) 0.0549(9) Uani d . 1
C C6 -0.1562(3) 0.4595(5) 0.1915(3) 0.0643(10) Uani d . 1
C C7 0.0026(3) 0.4639(5) 0.2064(3) 0.0553(8) Uani d . 1
C C8 0.1645(4) 0.4744(5) 0.3879(3) 0.0727(12) Uani d . 1
H H8A 0.1334 0.5770 0.4013 0.087 Uiso calc R 1
H H8B 0.1383 0.3753 0.4108 0.087 Uiso calc R 1
C C9 0.2782(5) 0.4839(6) 0.4432(4) 0.0892(16) Uani d . 1
H H9A 0.3086 0.3808 0.4295 0.107 Uiso calc R 1
H H9B 0.3038 0.5819 0.4190 0.107 Uiso calc R 1
C C10 0.3079(6) 0.5007(7) 0.5525(5) 0.112(2) Uani d . 1
H H10A 0.2865 0.4013 0.5796 0.135 Uiso calc R 1
H H10B 0.2797 0.6040 0.5688 0.135 Uiso calc R 1
C C11 0.4287(9) 0.5116(10) 0.5928(8) 0.177(5) Uani d D 1
H H11A 0.4547 0.4044 0.5782 0.212 Uiso calc R 1
H H11B 0.4474 0.6033 0.5580 0.212 Uiso calc R 1
C C12 0.4752(9) 0.5440(15) 0.7007(8) 0.204(5) Uani d D 1
H H12A 0.4560 0.4542 0.7362 0.245 Uiso calc R 1
H H12B 0.4520 0.6535 0.7159 0.245 Uiso calc R 1
C C13 0.5877(6) 0.5466(12) 0.7325(7) 0.171(4) Uani d . 1
H H13A 0.6107 0.4343 0.7236 0.257 Uiso calc R 1
H H13B 0.6189 0.5787 0.8016 0.257 Uiso calc R 1
H H13C 0.6055 0.6286 0.6928 0.257 Uiso calc R 1
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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 Pd1 N1 3_565 . 180.00(16)
N1 Pd1 Cl1 3_565 . 88.35(7)
N1 Pd1 Cl1 . . 91.65(7)
N1 Pd1 Cl1 3_565 3_565 91.65(7)
N1 Pd1 Cl1 . 3_565 88.35(7)
Cl1 Pd1 Cl1 . 3_565 180.0
C7 S1 C8 . . 101.6(2)
C7 N1 C5 . . 106.0(3)
C7 N1 Pd1 . . 126.9(3)
C5 N1 Pd1 . . 126.8(3)
C7 N2 C6 . . 107.9(3)
C7 N2 H2A . . 126.1
C6 N2 H2A . . 126.1
C2 C1 C6 . . 116.6(5)
C2 C1 H1 . . 121.7
C6 C1 H1 . . 121.7
C1 C2 C3 . . 122.2(5)
C1 C2 H2 . . 118.9
C3 C2 H2 . . 118.9
C4 C3 C2 . . 121.1(6)
C4 C3 H3 . . 119.4
C2 C3 H3 . . 119.4
C3 C4 C5 . . 117.5(5)
C3 C4 H4 . . 121.2
C5 C4 H4 . . 121.2
C4 C5 C6 . . 121.0(4)
C4 C5 N1 . . 130.5(4)
C6 C5 N1 . . 108.5(4)
N2 C6 C5 . . 106.1(3)
N2 C6 C1 . . 132.3(4)
C5 C6 C1 . . 121.6(4)
N1 C7 N2 . . 111.4(3)
N1 C7 S1 . . 121.8(3)
N2 C7 S1 . . 126.7(3)
C9 C8 S1 . . 109.5(4)
C9 C8 H8A . . 109.8
S1 C8 H8A . . 109.8
C9 C8 H8B . . 109.8
S1 C8 H8B . . 109.8
H8A C8 H8B . . 108.2
C10 C9 C8 . . 111.8(6)
C10 C9 H9A . . 109.2
C8 C9 H9A . . 109.2
C10 C9 H9B . . 109.2
C8 C9 H9B . . 109.2
H9A C9 H9B . . 107.9
C9 C10 C11 . . 102.3(7)
C9 C10 H10A . . 111.3
C11 C10 H10A . . 111.3
C9 C10 H10B . . 111.3
C11 C10 H10B . . 111.3
H10A C10 H10B . . 109.2
C12 C11 C10 . . 112.0(10)
C12 C11 H11A . . 109.2
C10 C11 H11A . . 109.2
C12 C11 H11B . . 109.2
C10 C11 H11B . . 109.2
H11A C11 H11B . . 107.9
C11 C12 C13 . . 108.5(11)
C11 C12 H12A . . 110.0
C13 C12 H12A . . 110.0
C11 C12 H12B . . 110.0
C13 C12 H12B . . 110.0
H12A C12 H12B . . 108.4
C12 C13 H13A . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C12 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Pd1 N1 3_565 2.009(3)
Pd1 N1 . 2.009(3)
Pd1 Cl1 . 2.2788(12)
Pd1 Cl1 3_565 2.2788(12)
S1 C7 . 1.729(4)
S1 C8 . 1.823(4)
N1 C7 . 1.331(5)
N1 C5 . 1.396(5)
N2 C7 . 1.350(4)
N2 C6 . 1.377(6)
N2 H2A . 0.8600
C1 C2 . 1.369(9)
C1 C6 . 1.398(6)
C1 H1 . 0.9300
C2 C3 . 1.396(9)
C2 H2 . 0.9300
C3 C4 . 1.375(7)
C3 H3 . 0.9300
C4 C5 . 1.388(6)
C4 H4 . 0.9300
C5 C6 . 1.390(5)
C8 C9 . 1.512(8)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C10 . 1.482(9)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C11 . 1.600(13)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 C12 . 1.468(9)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 C13 . 1.495(14)
C12 H12A . 0.9700
C12 H12B . 0.9700
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A Cl1 2_545 0.86 2.47 3.282(3) 156.6
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_site_symmetry_1
_geom_torsion
N1 Pd1 N1 C7 3_565 14E1(10)
Cl1 Pd1 N1 C7 . -87.1(3)
Cl1 Pd1 N1 C7 3_565 92.9(3)
N1 Pd1 N1 C5 3_565 -3E1(10)
Cl1 Pd1 N1 C5 . 98.7(2)
Cl1 Pd1 N1 C5 3_565 -81.3(2)
C6 C1 C2 C3 . 1.1(9)
C1 C2 C3 C4 . -0.9(9)
C2 C3 C4 C5 . 0.0(6)
C3 C4 C5 C6 . 0.5(5)
C3 C4 C5 N1 . -179.6(3)
C7 N1 C5 C4 . -179.1(3)
Pd1 N1 C5 C4 . -3.9(5)
C7 N1 C5 C6 . 0.8(4)
Pd1 N1 C5 C6 . 176.0(2)
C7 N2 C6 C5 . 0.6(5)
C7 N2 C6 C1 . 179.8(5)
C4 C5 C6 N2 . 179.0(3)
N1 C5 C6 N2 . -0.9(4)
C4 C5 C6 C1 . -0.3(6)
N1 C5 C6 C1 . 179.8(4)
C2 C1 C6 N2 . -179.7(5)
C2 C1 C6 C5 . -0.5(8)
C5 N1 C7 N2 . -0.5(4)
Pd1 N1 C7 N2 . -175.6(2)
C5 N1 C7 S1 . 178.8(2)
Pd1 N1 C7 S1 . 3.7(4)
C6 N2 C7 N1 . -0.1(5)
C6 N2 C7 S1 . -179.3(3)
C8 S1 C7 N1 . 167.7(3)
C8 S1 C7 N2 . -13.1(4)
C7 S1 C8 C9 . -175.7(3)
S1 C8 C9 C10 . 179.4(3)
C8 C9 C10 C11 . -179.0(4)
C9 C10 C11 C12 . 175.1(7)
C10 C11 C12 C13 . 178.2(7)
