#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/91/2229196.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_2229196
loop_
_publ_author_name
'Khaledi, Hamid'
'Mohd Ali, Hapipah'
_publ_section_title
;
 Bis{benzyl
 3-[(1H-indol-3-yl)methylidene]dithiocarbazato-κ²N³,S}palladium(II)
 pyridine disolvate
;
_journal_coeditor_code           PV2380
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m230
_journal_paper_doi               10.1107/S1600536811001991
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Pd (C17 H14 N3 S2)2], 2C5 H5 N'
_chemical_formula_moiety         'C34 H28 N6 Pd S4, 2(C5 H5 N)'
_chemical_formula_sum            'C44 H38 N8 Pd S4'
_chemical_formula_weight         913.46
_chemical_name_systematic
;
Bis{benzyl 3-[(1H-indol-3-yl)methylidene]dithiocarbazato-
κ²N³,S}palladium(II) pyridine disolvate
;
_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                62.534(2)
_cell_angle_beta                 78.494(2)
_cell_angle_gamma                78.985(2)
_cell_formula_units_Z            1
_cell_length_a                   9.9688(2)
_cell_length_b                   10.5041(2)
_cell_length_c                   10.9491(2)
_cell_measurement_reflns_used    2496
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.20
_cell_volume                     990.35(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8128
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  0.9647
_exptl_absorpt_correction_T_min  0.9311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.728
_refine_diff_density_min         -1.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3879
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0392
_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)+(0.0263P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0703
_reflns_number_gt                3045
_reflns_number_total             3879
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2380.cif
_cod_data_source_block           I
_cod_original_cell_volume        990.35(3)
_cod_database_code               2229196
_cod_database_fobs_code          2229196
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd1 0.0000 0.0000 0.0000 0.01415(11) Uani d S 1 . .
S S1 0.22662(8) -0.07299(8) 0.03590(8) 0.01946(19) Uani d . 1 . .
S S2 0.39814(8) 0.01851(8) 0.15858(8) 0.01993(19) Uani d . 1 . .
N N1 -0.0326(3) 0.4905(3) 0.2098(3) 0.0209(6) Uani d D 1 . .
H H1N 0.014(3) 0.528(3) 0.240(3) 0.025 Uiso d D 1 . .
N N2 0.0161(3) 0.1372(2) 0.0784(2) 0.0161(6) Uani d . 1 . .
N N3 0.1382(3) 0.1317(2) 0.1281(2) 0.0168(6) Uani d . 1 . .
C C1 0.0172(3) 0.3767(3) 0.1816(3) 0.0211(7) Uani d . 1 . .
H H1 0.1081 0.3286 0.1913 0.025 Uiso calc R 1 . .
C C2 -0.0838(3) 0.3404(3) 0.1364(3) 0.0175(7) Uani d . 1 . .
C C3 -0.2052(3) 0.4404(3) 0.1403(3) 0.0175(7) Uani d . 1 . .
C C4 -0.3413(3) 0.4581(3) 0.1129(3) 0.0207(7) Uani d . 1 . .
H H4 -0.3696 0.3974 0.0822 0.025 Uiso calc R 1 . .
C C5 -0.4324(3) 0.5660(3) 0.1317(3) 0.0247(8) Uani d . 1 . .
H H5 -0.5249 0.5785 0.1146 0.030 Uiso calc R 1 . .
C C6 -0.3925(4) 0.6577(3) 0.1754(3) 0.0257(8) Uani d . 1 . .
H H6 -0.4580 0.7315 0.1863 0.031 Uiso calc R 1 . .
C C7 -0.2600(3) 0.6428(3) 0.2026(3) 0.0236(8) Uani d . 1 . .
H H7 -0.2324 0.7052 0.2317 0.028 Uiso calc R 1 . .
C C8 -0.1682(3) 0.5327(3) 0.1860(3) 0.0185(7) Uani d . 1 . .
C C9 -0.0809(3) 0.2353(3) 0.0870(3) 0.0161(7) Uani d . 1 . .
H H9 -0.1638 0.2379 0.0551 0.019 Uiso calc R 1 . .
C C10 0.2357(3) 0.0394(3) 0.1092(3) 0.0155(7) Uani d . 1 . .
C C11 0.3916(3) 0.1657(3) 0.2031(3) 0.0192(7) Uani d . 1 . .
H H11A 0.4837 0.2004 0.1736 0.023 Uiso calc R 1 . .
H H11B 0.3258 0.2461 0.1484 0.023 Uiso calc R 1 . .
C C12 0.3507(3) 0.1328(3) 0.3543(3) 0.0180(7) Uani d . 1 . .
C C13 0.2418(3) 0.0539(3) 0.4334(3) 0.0243(7) Uani d . 1 . .
H H13 0.1898 0.0208 0.3920 0.029 Uiso calc R 1 . .
C C14 0.2083(4) 0.0229(3) 0.5724(3) 0.0283(8) Uani d . 1 . .
H H14 0.1344 -0.0324 0.6260 0.034 Uiso calc R 1 . .
C C15 0.2820(4) 0.0720(3) 0.6337(3) 0.0289(8) Uani d . 1 . .
H H15 0.2590 0.0507 0.7291 0.035 Uiso calc R 1 . .
C C16 0.3883(4) 0.1516(3) 0.5552(3) 0.0265(8) Uani d . 1 . .
H H16 0.4383 0.1868 0.5964 0.032 Uiso calc R 1 . .
C C17 0.4238(3) 0.1814(3) 0.4174(3) 0.0209(7) Uani d . 1 . .
H H17 0.4988 0.2356 0.3650 0.025 Uiso calc R 1 . .
N N4 0.1071(3) 0.5947(3) 0.3379(3) 0.0247(6) Uani d . 1 . .
C C18 0.0482(4) 0.6915(3) 0.3856(3) 0.0293(8) Uani d . 1 . .
H H18 -0.0442 0.7315 0.3704 0.035 Uiso calc R 1 . .
C C19 0.1138(4) 0.7360(4) 0.4550(3) 0.0322(8) Uani d . 1 . .
H H19 0.0671 0.8044 0.4875 0.039 Uiso calc R 1 . .
C C20 0.2470(4) 0.6811(4) 0.4771(4) 0.0392(10) Uani d . 1 . .
H H20 0.2951 0.7107 0.5245 0.047 Uiso calc R 1 . .
C C21 0.3098(4) 0.5814(4) 0.4286(4) 0.0435(10) Uani d . 1 . .
H H21 0.4026 0.5412 0.4416 0.052 Uiso calc R 1 . .
C C22 0.2362(4) 0.5409(4) 0.3610(3) 0.0327(9) Uani d . 1 . .
H H22 0.2799 0.4710 0.3293 0.039 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'
Pd Pd -0.9988 1.0072 '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'
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
_geom_angle_publ_flag
N2 Pd1 N2 2 . 180.0 ?
N2 Pd1 S1 2 2 83.22(7) ?
N2 Pd1 S1 . 2 96.78(7) ?
N2 Pd1 S1 2 . 96.78(7) ?
N2 Pd1 S1 . . 83.22(7) ?
S1 Pd1 S1 2 . 180.0 ?
C10 S1 Pd1 . . 95.95(11) ?
C10 S2 C11 . . 104.39(14) ?
C1 N1 C8 . . 109.9(3) ?
C1 N1 H1N . . 124(2) ?
C8 N1 H1N . . 126(2) ?
C9 N2 N3 . . 114.6(2) ?
C9 N2 Pd1 . . 124.4(2) ?
N3 N2 Pd1 . . 121.06(17) ?
C10 N3 N2 . . 112.8(2) ?
N1 C1 C2 . . 110.1(3) ?
N1 C1 H1 . . 125.0 ?
C2 C1 H1 . . 125.0 ?
C1 C2 C9 . . 131.8(3) ?
C1 C2 C3 . . 105.7(3) ?
C9 C2 C3 . . 122.4(3) ?
C8 C3 C4 . . 118.9(3) ?
C8 C3 C2 . . 106.7(3) ?
C4 C3 C2 . . 134.3(3) ?
C5 C4 C3 . . 118.1(3) ?
C5 C4 H4 . . 121.0 ?
C3 C4 H4 . . 121.0 ?
C4 C5 C6 . . 121.9(3) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C7 C6 C5 . . 121.1(3) ?
C7 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C6 C7 C8 . . 117.3(3) ?
C6 C7 H7 . . 121.4 ?
C8 C7 H7 . . 121.4 ?
N1 C8 C7 . . 129.7(3) ?
N1 C8 C3 . . 107.6(2) ?
C7 C8 C3 . . 122.7(3) ?
N2 C9 C2 . . 130.7(3) ?
N2 C9 H9 . . 114.7 ?
C2 C9 H9 . . 114.7 ?
N3 C10 S1 . . 126.8(2) ?
N3 C10 S2 . . 120.5(2) ?
S1 C10 S2 . . 112.65(16) ?
C12 C11 S2 . . 116.6(2) ?
C12 C11 H11A . . 108.1 ?
S2 C11 H11A . . 108.1 ?
C12 C11 H11B . . 108.1 ?
S2 C11 H11B . . 108.1 ?
H11A C11 H11B . . 107.3 ?
C13 C12 C17 . . 118.5(3) ?
C13 C12 C11 . . 121.7(3) ?
C17 C12 C11 . . 119.8(3) ?
C14 C13 C12 . . 120.4(3) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 120.5(3) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C16 C15 C14 . . 119.2(3) ?
C16 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C15 C16 C17 . . 120.9(3) ?
C15 C16 H16 . . 119.5 ?
C17 C16 H16 . . 119.5 ?
C16 C17 C12 . . 120.5(3) ?
C16 C17 H17 . . 119.7 ?
C12 C17 H17 . . 119.7 ?
C22 N4 C18 . . 116.7(3) ?
N4 C18 C19 . . 123.6(3) ?
N4 C18 H18 . . 118.2 ?
C19 C18 H18 . . 118.2 ?
C18 C19 C20 . . 119.3(3) ?
C18 C19 H19 . . 120.4 ?
C20 C19 H19 . . 120.4 ?
C19 C20 C21 . . 118.1(4) ?
C19 C20 H20 . . 120.9 ?
C21 C20 H20 . . 120.9 ?
C22 C21 C20 . . 119.1(4) ?
C22 C21 H21 . . 120.5 ?
C20 C21 H21 . . 120.5 ?
N4 C22 C21 . . 123.2(3) ?
N4 C22 H22 . . 118.4 ?
C21 C22 H22 . . 118.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Pd1 N2 2 2.031(2) ?
Pd1 N2 . 2.031(2) ?
Pd1 S1 2 2.2936(8) ?
Pd1 S1 . 2.2936(8) ?
S1 C10 . 1.729(3) ?
S2 C10 . 1.751(3) ?
S2 C11 . 1.810(3) ?
N1 C1 . 1.350(4) ?
N1 C8 . 1.377(4) ?
N1 H1N . 0.857(18) ?
N2 C9 . 1.296(3) ?
N2 N3 . 1.411(3) ?
N3 C10 . 1.294(3) ?
C1 C2 . 1.387(4) ?
C1 H1 . 0.9500 ?
C2 C9 . 1.430(4) ?
C2 C3 . 1.450(4) ?
C3 C8 . 1.408(4) ?
C3 C4 . 1.408(4) ?
C4 C5 . 1.378(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.400(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.376(5) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.390(4) ?
C7 H7 . 0.9500 ?
C9 H9 . 0.9500 ?
C11 C12 . 1.510(4) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.387(4) ?
C12 C17 . 1.393(4) ?
C13 C14 . 1.384(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.384(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.369(5) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.376(4) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
N4 C22 . 1.326(4) ?
N4 C18 . 1.339(4) ?
C18 C19 . 1.365(5) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.365(5) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.378(5) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.376(5) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
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
_geom_hbond_publ_flag
N1 H1N N4 . 0.86(2) 1.96(2) 2.808(4) 171(3) y
C9 H9 S1 2 0.95 2.58 3.267(3) 130 y
C1 H1 N3 . 0.95 2.42 2.889(4) 110 n
C11 H11B N3 . 0.99 2.50 2.937(4) 106 n
