#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:39:18 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179071 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/33/4303318.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_4303318
loop_
_publ_author_name
'Sebastian Scheuermann'
'Biprajit Sarkar'
'Michael Bolte'
'Jan W. Bats'
'Hans-Wolfram Lerner'
'Matthias Wagner'
_publ_section_title
;
Single-Electron Transfer in Palladium Complexes of
1,4-Naphthoquinone-Containing Bis(pyrazol-1-yl)methane Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9385
_journal_page_last               9392
_journal_paper_doi               10.1021/ic9013015
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C18 H14 Cl2 N4 O2 Pd , 1.33(C2 H3 N)'
_chemical_formula_sum            'C20.67 H18 Cl2 N5.33 O2 Pd'
_chemical_formula_weight         550.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           161
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'R 3 -2"c'
_symmetry_space_group_name_H-M   'R 3 c :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   23.3444(17)
_cell_length_b                   23.3444(17)
_cell_length_c                   21.1904(16)
_cell_measurement_reflns_used    410
_cell_measurement_temperature    165(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     10000.8(13)
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      165(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  SIEMENS_SMART_1K_CCD
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            42560
_diffrn_reflns_theta_full        30.88
_diffrn_reflns_theta_max         30.88
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1200
_diffrn_standards_number         872
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             4956
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.025(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         6496
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.02P)²+3P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0412
_refine_ls_wR_factor_ref         0.0438
_reflns_number_gt                5781
_reflns_number_total             6496
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic9013015_si_001_3.cif
_cod_data_source_block           scheuermann2_Compound_5
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               4303318
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
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 0.097997(7) 0.302502(7) 0.837370(7) 0.01791(4) Uani 1 1 d . . .
Cl1 Cl 0.12912(3) 0.25735(3) 0.91613(2) 0.02834(12) Uani 1 1 d . . .
Cl2 Cl 0.11179(3) 0.38784(3) 0.90029(2) 0.02982(12) Uani 1 1 d . . .
N12 N 0.07029(8) 0.33932(8) 0.76476(8) 0.0226(4) Uani 1 1 d . . .
N21 N 0.04314(8) 0.20821(8) 0.73129(8) 0.0186(3) Uani 1 1 d . . .
N5 N -0.06015(14) 0.05853(13) 0.59395(13) 0.0650(8) Uani 1 1 d . . .
C2 C -0.04726(9) 0.20858(9) 0.79263(9) 0.0177(4) Uani 1 1 d . . .
C24 C 0.10530(11) 0.16364(11) 0.71609(11) 0.0291(5) Uani 1 1 d . . .
H24A H 0.1239 0.1389 0.6991 0.035 Uiso 1 1 calc R . .
N11 N 0.02480(8) 0.29865(8) 0.72124(7) 0.0196(3) Uani 1 1 d . . .
C12 C -0.05634(10) 0.19175(11) 0.67593(9) 0.0245(4) Uani 1 1 d . . .
H12A H -0.0321 0.2056 0.6359 0.037 Uiso 1 1 calc R . .
H12B H -0.0912 0.2035 0.6760 0.037 Uiso 1 1 calc R . .
H12C H -0.0763 0.1438 0.6808 0.037 Uiso 1 1 calc R . .
C6 C -0.11162(10) 0.12404(10) 0.87888(9) 0.0209(4) Uani 1 1 d . . .
O1 O -0.06019(8) 0.10137(7) 0.79352(7) 0.0310(3) Uani 1 1 d . . .
O2 O -0.12034(8) 0.27307(8) 0.89841(7) 0.0295(3) Uani 1 1 d . . .
C5 C -0.12868(10) 0.16792(10) 0.90643(9) 0.0203(4) Uani 1 1 d . . .
C1 C -0.07218(10) 0.14079(10) 0.81954(9) 0.0204(4) Uani 1 1 d . . .
N22 N 0.08828(8) 0.23032(8) 0.77890(8) 0.0213(4) Uani 1 1 d . . .
C3 C -0.06552(10) 0.24938(10) 0.81932(9) 0.0202(4) Uani 1 1 d . . .
H3A H -0.0511 0.2912 0.8001 0.024 Uiso 1 1 calc R . .
C10 C -0.16664(12) 0.15039(11) 0.96118(11) 0.0287(5) Uani 1 1 d . . .
H10A H -0.1785 0.1801 0.9794 0.034 Uiso 1 1 calc R . .
C11 C -0.00885(9) 0.22653(10) 0.73041(9) 0.0188(4) Uani 1 1 d . . .
C15 C 0.01340(11) 0.33494(11) 0.67869(9) 0.0260(5) Uani 1 1 d . . .
H15A H -0.0166 0.3182 0.6442 0.031 Uiso 1 1 calc R . .
C14 C 0.05276(12) 0.40023(12) 0.69416(11) 0.0330(5) Uani 1 1 d . . .
H14A H 0.0557 0.4373 0.6727 0.040 Uiso 1 1 calc R . .
C9 C -0.18701(12) 0.08963(12) 0.98894(11) 0.0333(5) Uani 1 1 d . . .
H9A H -0.2124 0.0778 1.0266 0.040 Uiso 1 1 calc R . .
C4 C -0.10645(10) 0.23308(10) 0.87650(9) 0.0213(4) Uani 1 1 d . . .
C25 C 0.05239(10) 0.16734(11) 0.69319(9) 0.0247(4) Uani 1 1 d . . .
H25A H 0.0269 0.1451 0.6570 0.030 Uiso 1 1 calc R . .
N6 N 0.0000 0.0000 0.9014(4) 0.117(3) Uani 1 3 d S . .
C8 C -0.17016(12) 0.04575(11) 0.96155(11) 0.0326(5) Uani 1 1 d . . .
H8A H -0.1845 0.0039 0.9807 0.039 Uiso 1 1 calc R . .
C7 C -0.13294(11) 0.06223(11) 0.90702(11) 0.0278(5) Uani 1 1 d . . .
H7A H -0.1218 0.0319 0.8887 0.033 Uiso 1 1 calc R . .
C23 C 0.12602(10) 0.20360(11) 0.76943(10) 0.0266(5) Uani 1 1 d . . .
H23A H 0.1622 0.2108 0.7954 0.032 Uiso 1 1 calc R . .
C13 C 0.08758(11) 0.40105(10) 0.74772(11) 0.0302(5) Uani 1 1 d . . .
H13A H 0.1191 0.4399 0.7691 0.036 Uiso 1 1 calc R . .
C26 C -0.08771(13) 0.02063(14) 0.55648(13) 0.0430(6) Uani 1 1 d . . .
C29 C 0.0000 0.0000 0.7814(4) 0.0611(19) Uani 1 3 d S . .
C27 C -0.12415(17) -0.02884(18) 0.50863(16) 0.0685(9) Uani 1 1 d . . .
H27A H -0.1539 -0.0712 0.5290 0.103 Uiso 1 1 calc R . .
H27B H -0.0931 -0.0339 0.4813 0.103 Uiso 1 1 calc R . .
H27C H -0.1501 -0.0149 0.4832 0.103 Uiso 1 1 calc R . .
C28 C 0.0000 0.0000 0.8491(5) 0.076(2) Uani 1 3 d S . .
H29A H 0.031(3) 0.002(4) 0.770(2) 0.15(2) Uiso 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'
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'
Cl Cl 0.1484 0.1585 '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
N22 Pd1 N12 87.79(7) . . ?
N22 Pd1 Cl1 89.55(5) . . ?
N12 Pd1 Cl1 177.32(5) . . ?
N22 Pd1 Cl2 177.40(5) . . ?
N12 Pd1 Cl2 90.52(5) . . ?
Cl1 Pd1 Cl2 92.14(2) . . ?
C13 N12 N11 106.09(17) . . ?
C13 N12 Pd1 132.52(15) . . ?
N11 N12 Pd1 121.38(12) . . ?
C25 N21 N22 110.17(16) . . ?
C25 N21 C11 130.12(17) . . ?
N22 N21 C11 119.55(16) . . ?
C3 C2 C1 119.58(17) . . ?
C3 C2 C11 121.16(18) . . ?
C1 C2 C11 118.79(17) . . ?
C25 C24 C23 105.55(19) . . ?
C15 N11 N12 110.02(17) . . ?
C15 N11 C11 130.18(17) . . ?
N12 N11 C11 119.34(15) . . ?
C5 C6 C7 119.44(18) . . ?
C5 C6 C1 121.63(18) . . ?
C7 C6 C1 118.92(18) . . ?
C10 C5 C6 120.33(19) . . ?
C10 C5 C4 120.23(19) . . ?
C6 C5 C4 119.43(17) . . ?
O1 C1 C6 121.88(18) . . ?
O1 C1 C2 120.69(17) . . ?
C6 C1 C2 117.43(17) . . ?
C23 N22 N21 106.29(16) . . ?
C23 N22 Pd1 131.68(14) . . ?
N21 N22 Pd1 121.07(13) . . ?
C2 C3 C4 123.88(18) . . ?
C9 C10 C5 119.9(2) . . ?
N11 C11 N21 106.70(15) . . ?
N11 C11 C12 109.85(16) . . ?
N21 C11 C12 109.89(16) . . ?
N11 C11 C2 109.35(16) . . ?
N21 C11 C2 111.36(15) . . ?
C12 C11 C2 109.65(16) . . ?
N11 C15 C14 107.78(19) . . ?
C15 C14 C13 105.8(2) . . ?
C10 C9 C8 119.9(2) . . ?
O2 C4 C3 120.09(18) . . ?
O2 C4 C5 122.06(18) . . ?
C3 C4 C5 117.84(17) . . ?
N21 C25 C24 107.55(18) . . ?
C7 C8 C9 120.9(2) . . ?
C8 C7 C6 119.5(2) . . ?
N22 C23 C24 110.44(19) . . ?
N12 C13 C14 110.3(2) . . ?
N5 C26 C27 179.2(4) . . ?
N6 C28 C29 180.000(6) . . ?
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 N22 2.0110(17) . ?
Pd1 N12 2.0201(17) . ?
Pd1 Cl1 2.2780(5) . ?
Pd1 Cl2 2.2823(5) . ?
N12 C13 1.337(3) . ?
N12 N11 1.368(2) . ?
N21 C25 1.347(3) . ?
N21 N22 1.361(2) . ?
N21 C11 1.475(2) . ?
N5 C26 1.122(3) . ?
C2 C3 1.347(3) . ?
C2 C1 1.499(3) . ?
C2 C11 1.530(3) . ?
C24 C25 1.369(3) . ?
C24 C23 1.390(3) . ?
N11 C15 1.352(3) . ?
N11 C11 1.472(3) . ?
C12 C11 1.523(3) . ?
C6 C5 1.399(3) . ?
C6 C7 1.403(3) . ?
C6 C1 1.491(3) . ?
O1 C1 1.219(2) . ?
O2 C4 1.223(2) . ?
C5 C10 1.391(3) . ?
C5 C4 1.482(3) . ?
N22 C23 1.325(3) . ?
C3 C4 1.470(3) . ?
C10 C9 1.382(3) . ?
C15 C14 1.369(3) . ?
C14 C13 1.390(3) . ?
C9 C8 1.394(3) . ?
N6 C28 1.110(11) . ?
C8 C7 1.380(3) . ?
C26 C27 1.450(4) . ?
C29 C28 1.435(12) . ?
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
N22 Pd1 N12 C13 -145.9(2) . . . . ?
Cl1 Pd1 N12 C13 -141.7(10) . . . . ?
Cl2 Pd1 N12 C13 32.2(2) . . . . ?
N22 Pd1 N12 N11 34.86(15) . . . . ?
Cl1 Pd1 N12 N11 39.0(12) . . . . ?
Cl2 Pd1 N12 N11 -147.10(14) . . . . ?
C13 N12 N11 C15 -1.1(2) . . . . ?
Pd1 N12 N11 C15 178.31(13) . . . . ?
C13 N12 N11 C11 -174.19(17) . . . . ?
Pd1 N12 N11 C11 5.3(2) . . . . ?
C7 C6 C5 C10 -0.2(3) . . . . ?
C1 C6 C5 C10 178.74(19) . . . . ?
C7 C6 C5 C4 -179.68(18) . . . . ?
C1 C6 C5 C4 -0.7(3) . . . . ?
C5 C6 C1 O1 -176.02(19) . . . . ?
C7 C6 C1 O1 2.9(3) . . . . ?
C5 C6 C1 C2 4.2(3) . . . . ?
C7 C6 C1 C2 -176.90(18) . . . . ?
C3 C2 C1 O1 174.73(19) . . . . ?
C11 C2 C1 O1 2.5(3) . . . . ?
C3 C2 C1 C6 -5.4(3) . . . . ?
C11 C2 C1 C6 -177.70(16) . . . . ?
C25 N21 N22 C23 0.9(2) . . . . ?
C11 N21 N22 C23 176.72(16) . . . . ?
C25 N21 N22 Pd1 170.91(13) . . . . ?
C11 N21 N22 Pd1 -13.3(2) . . . . ?
N12 Pd1 N22 C23 136.40(19) . . . . ?
Cl1 Pd1 N22 C23 -43.41(19) . . . . ?
Cl2 Pd1 N22 C23 87.2(12) . . . . ?
N12 Pd1 N22 N21 -30.74(15) . . . . ?
Cl1 Pd1 N22 N21 149.45(14) . . . . ?
Cl2 Pd1 N22 N21 -79.9(11) . . . . ?
C1 C2 C3 C4 3.4(3) . . . . ?
C11 C2 C3 C4 175.47(18) . . . . ?
C6 C5 C10 C9 0.7(3) . . . . ?
C4 C5 C10 C9 -179.8(2) . . . . ?
C15 N11 C11 N21 128.3(2) . . . . ?
N12 N11 C11 N21 -60.3(2) . . . . ?
C15 N11 C11 C12 9.2(3) . . . . ?
N12 N11 C11 C12 -179.35(16) . . . . ?
C15 N11 C11 C2 -111.2(2) . . . . ?
N12 N11 C11 C2 60.3(2) . . . . ?
C25 N21 C11 N11 -119.7(2) . . . . ?
N22 N21 C11 N11 65.4(2) . . . . ?
C25 N21 C11 C12 -0.7(3) . . . . ?
N22 N21 C11 C12 -175.55(16) . . . . ?
C25 N21 C11 C2 121.0(2) . . . . ?
N22 N21 C11 C2 -53.8(2) . . . . ?
C3 C2 C11 N11 22.1(2) . . . . ?
C1 C2 C11 N11 -165.77(16) . . . . ?
C3 C2 C11 N21 139.76(18) . . . . ?
C1 C2 C11 N21 -48.1(2) . . . . ?
C3 C2 C11 C12 -98.4(2) . . . . ?
C1 C2 C11 C12 73.7(2) . . . . ?
N12 N11 C15 C14 0.9(2) . . . . ?
C11 N11 C15 C14 172.98(19) . . . . ?
N11 C15 C14 C13 -0.3(3) . . . . ?
C5 C10 C9 C8 -0.8(3) . . . . ?
C2 C3 C4 O2 179.10(19) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C10 C5 C4 O2 0.0(3) . . . . ?
C6 C5 C4 O2 179.5(2) . . . . ?
C10 C5 C4 C3 178.99(19) . . . . ?
C6 C5 C4 C3 -1.5(3) . . . . ?
N22 N21 C25 C24 -0.9(2) . . . . ?
C11 N21 C25 C24 -176.15(19) . . . . ?
C23 C24 C25 N21 0.5(2) . . . . ?
C10 C9 C8 C7 0.4(4) . . . . ?
C9 C8 C7 C6 0.2(4) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C1 C6 C7 C8 -179.2(2) . . . . ?
N21 N22 C23 C24 -0.5(2) . . . . ?
Pd1 N22 C23 C24 -169.07(15) . . . . ?
C25 C24 C23 N22 0.0(3) . . . . ?
N11 N12 C13 C14 0.9(2) . . . . ?
Pd1 N12 C13 C14 -178.44(16) . . . . ?
C15 C14 C13 N12 -0.4(3) . . . . ?
