#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:52:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178705 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/16/4081698.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_4081698
loop_
_publ_author_name
'Oloo, Williamson N.'
'Zavalij, Peter Y.'
'Vedernikov, Andrei N.'
_publ_section_title
;
 Palladium(IV) Monohydrocarbyls: Mechanistic Study of the Ligand-Enabled
 Oxidation of Palladium(II) Complexes with H2O2in Water
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              5601
_journal_paper_doi               10.1021/om400878u
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C33 H22 F2 N4 O4 Pd2, 2(C H Cl3)'
_chemical_formula_sum            'C35 H24 Cl6 F2 N4 O4 Pd2'
_chemical_formula_weight         1028.08
_chemical_name_common            Pd2-complex
_chemical_name_systematic
;
Pd2-complex
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 & ZCIF'
_cell_angle_alpha                90.00
_cell_angle_beta                 111.8383(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.1268(14)
_cell_length_b                   9.2511(6)
_cell_length_c                   20.5534(14)
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.4
_cell_volume                     3728.8(4)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2005)'
_computing_data_reduction        Apex2
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 11.198
_diffrn_detector_type            'Bruker Smart Apex II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      610,610,610,96
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.0049416
_diffrn_orient_matrix_UB_12      0.1049261
_diffrn_orient_matrix_UB_13      -0.0088156
_diffrn_orient_matrix_UB_21      0.0469386
_diffrn_orient_matrix_UB_22      -0.0003328
_diffrn_orient_matrix_UB_23      0.0369599
_diffrn_orient_matrix_UB_31      0.0193048
_diffrn_orient_matrix_UB_32      -0.0259871
_diffrn_orient_matrix_UB_33      -0.0361060
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14714
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.08
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    1.450
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2024
_exptl_crystal_id                'VEdern/Oloo Pd-complex 150K'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.949
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     148
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.036P)²+26.7P], P=(max(Fo²,0)+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                2823
_reflns_number_total             3281
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400878u_si_002.cif
_cod_data_source_block           2165
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4081698
#BEGIN Tags that were not found in dictionaries:
_diffrn_measurement_frame_width-ccd -0.30
_diffrn_measurement_total_frames-ccd 1926
_diffrn_measurement_frame_time-ccd 30
_diffrn_measurement_total_time-ccd 18.7
_diffrn_detector_distance-ccd    5.000
_diffrn_measurement_frame_size-ccd 512
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Pd1 Pd 0.368036(15) 0.85799(3) 0.140153(15) 0.02711(12) Uani 1 1 d . . .
N11 N 0.38813(17) 0.7379(4) 0.22670(17) 0.0306(8) Uani 1 1 d . . .
C12 C 0.3418(2) 0.6594(5) 0.2426(2) 0.0357(10) Uani 1 1 d . . .
H12 H 0.2964 0.6523 0.2095 0.043 Uiso 1 1 calc R . .
C13 C 0.3595(2) 0.5899(5) 0.3060(2) 0.0379(10) Uani 1 1 d . . .
H13 H 0.3265 0.5356 0.3167 0.046 Uiso 1 1 calc R . .
C14 C 0.4255(2) 0.5995(5) 0.3538(2) 0.0389(11) Uani 1 1 d . . .
H14 H 0.4385 0.5509 0.3975 0.047 Uiso 1 1 calc R . .
C15 C 0.4727(2) 0.6814(5) 0.3373(2) 0.0364(10) Uani 1 1 d . . .
H15 H 0.5183 0.6903 0.3698 0.044 Uiso 1 1 calc R . .
C16 C 0.4523(2) 0.7497(5) 0.2729(2) 0.0283(9) Uani 1 1 d . . .
C17 C 0.5000 0.8458(6) 0.2500 0.0281(12) Uani 1 2 d S . .
O1 O 0.46132(13) 0.9330(3) 0.19384(14) 0.0304(6) Uani 1 1 d . . .
N21 N 0.35472(17) 0.9821(4) 0.05558(17) 0.0303(8) Uani 1 1 d . . .
C22 C 0.4120(2) 1.0237(5) 0.0459(2) 0.0360(10) Uani 1 1 d . . .
H22 H 0.4549 1.0050 0.0821 0.043 Uiso 1 1 calc R . .
C23 C 0.4111(2) 1.0917(6) -0.0139(2) 0.0441(12) Uani 1 1 d . . .
H23 H 0.4523 1.1205 -0.0187 0.053 Uiso 1 1 calc R . .
C24 C 0.3489(3) 1.1168(6) -0.0666(3) 0.0505(13) Uani 1 1 d . . .
H24 H 0.3467 1.1614 -0.1090 0.061 Uiso 1 1 calc R . .
C25 C 0.2899(2) 1.0768(6) -0.0575(2) 0.0413(11) Uani 1 1 d . . .
H25 H 0.2470 1.0935 -0.0939 0.050 Uiso 1 1 calc R . .
C26 C 0.2929(2) 1.0111(5) 0.0058(2) 0.0315(9) Uani 1 1 d . . .
C31 C 0.2248(2) 0.8529(5) 0.0566(2) 0.0302(9) Uani 1 1 d . . .
C32 C 0.1589(2) 0.8109(5) 0.0532(2) 0.0322(9) Uani 1 1 d . . .
H32 H 0.1537 0.7291 0.0787 0.039 Uiso 1 1 calc R . .
C33 C 0.1036(2) 0.8880(5) 0.0136(2) 0.0360(10) Uani 1 1 d . . .
C34 C 0.1067(2) 1.0123(5) -0.0235(2) 0.0404(11) Uani 1 1 d . . .
H34 H 0.0671 1.0675 -0.0485 0.048 Uiso 1 1 calc R . .
C35 C 0.1700(2) 1.0502(5) -0.0218(2) 0.0381(10) Uani 1 1 d . . .
H35 H 0.1738 1.1334 -0.0471 0.046 Uiso 1 1 calc R . .
C36 C 0.2294(2) 0.9723(5) 0.0156(2) 0.0311(9) Uani 1 1 d . . .
O2 O 0.27609(14) 0.7734(3) 0.09587(15) 0.0361(7) Uani 1 1 d . . .
F1 F 0.04054(12) 0.8436(3) 0.01105(13) 0.0435(7) Uani 1 1 d . . .
C1 C 0.4011(3) 0.1919(7) 0.2461(3) 0.0526(11) Uani 0.752(3) 1 d PDU A 1
H1 H 0.4241 0.1069 0.2343 0.063 Uiso 0.752(3) 1 calc PR A 1
Cl1 Cl 0.4363(5) 0.2220(10) 0.33609(18) 0.0590(6) Uani 0.752(3) 1 d PDU A 1
Cl2 Cl 0.41081(13) 0.3446(3) 0.19920(12) 0.0663(6) Uani 0.752(3) 1 d PDU A 1
Cl3 Cl 0.31285(12) 0.1576(4) 0.21846(19) 0.1017(11) Uani 0.752(3) 1 d PDU A 1
C1A C 0.4058(9) 0.145(2) 0.2649(9) 0.0526(11) Uani 0.074(3) 1 d PDU B 2
H1A H 0.4285 0.0798 0.2416 0.063 Uiso 0.074(3) 1 calc PR B 2
Cl1A Cl 0.4656(8) 0.272(2) 0.3155(9) 0.0590(6) Uani 0.074(3) 1 d PDU B 2
Cl2A Cl 0.3367(8) 0.231(3) 0.2000(10) 0.069(5) Uani 0.074(3) 1 d PDU B 2
Cl3A Cl 0.3752(11) 0.0411(19) 0.3184(10) 0.070(5) Uani 0.074(3) 1 d PDU B 2
C1B C 0.3865(14) 0.140(4) 0.2689(13) 0.0526(11) Uani 0.174(4) 1 d PDU C 3
H1B H 0.4177 0.0671 0.2606 0.063 Uiso 0.174(4) 1 calc PR C 3
Cl1B Cl 0.440(2) 0.227(5) 0.3456(8) 0.0590(6) Uani 0.174(4) 1 d PDU C 3
Cl2B Cl 0.3760(10) 0.2769(16) 0.1979(6) 0.109(5) Uani 0.174(4) 1 d PDU C 3
Cl3B Cl 0.3259(6) 0.0516(16) 0.2631(9) 0.109(4) Uani 0.174(4) 1 d PDU C 3
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'
F F 0.0171 0.0103 '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
O2 Pd1 O1 174.10(11) . .
O2 Pd1 N11 92.11(13) . .
O1 Pd1 N11 82.07(12) . .
O2 Pd1 N21 91.74(13) . .
O1 Pd1 N21 94.10(12) . .
N11 Pd1 N21 176.06(13) . .
C16 N11 C12 120.4(4) . .
C16 N11 Pd1 114.1(3) . .
C12 N11 Pd1 125.4(3) . .
N11 C12 C13 120.9(4) . .
N11 C12 H12 119.5 . .
C13 C12 H12 119.5 . .
C12 C13 C14 119.6(4) . .
C12 C13 H13 120.2 . .
C14 C13 H13 120.2 . .
C13 C14 C15 119.2(4) . .
C13 C14 H14 120.4 . .
C15 C14 H14 120.4 . .
C16 C15 C14 119.1(4) . .
C16 C15 H15 120.4 . .
C14 C15 H15 120.4 . .
N11 C16 C15 120.9(4) . .
N11 C16 C17 115.8(3) . .
C15 C16 C17 123.3(3) . .
O1 C17 O1 109.5(5) 2_655 .
O1 C17 C16 109.20(18) 2_655 .
O1 C17 C16 109.69(19) . .
O1 C17 C16 109.69(19) 2_655 2_655
O1 C17 C16 109.20(18) . 2_655
C16 C17 C16 109.6(5) . 2_655
C17 O1 Pd1 114.3(2) . .
C26 N21 C22 119.8(4) . .
C26 N21 Pd1 123.5(3) . .
C22 N21 Pd1 116.3(3) . .
N21 C22 C23 123.1(4) . .
N21 C22 H22 118.4 . .
C23 C22 H22 118.4 . .
C22 C23 C24 118.2(4) . .
C22 C23 H23 120.9 . .
C24 C23 H23 120.9 . .
C23 C24 C25 119.6(4) . .
C23 C24 H24 120.2 . .
C25 C24 H24 120.2 . .
C24 C25 C26 120.4(4) . .
C24 C25 H25 119.8 . .
C26 C25 H25 119.8 . .
N21 C26 C25 118.8(4) . .
N21 C26 C36 121.3(4) . .
C25 C26 C36 119.9(4) . .
O2 C31 C36 125.5(4) . .
O2 C31 C32 116.6(4) . .
C36 C31 C32 117.8(4) . .
C33 C32 C31 119.7(4) . .
C33 C32 H32 120.1 . .
C31 C32 H32 120.1 . .
C32 C33 F1 118.2(4) . .
C32 C33 C34 124.1(4) . .
F1 C33 C34 117.7(4) . .
C35 C34 C33 116.0(4) . .
C35 C34 H34 122.0 . .
C33 C34 H34 122.0 . .
C34 C35 C36 123.3(4) . .
C34 C35 H35 118.3 . .
C36 C35 H35 118.3 . .
C35 C36 C31 118.8(4) . .
C35 C36 C26 118.4(4) . .
C31 C36 C26 122.6(4) . .
C31 O2 Pd1 120.5(3) . .
Cl1 C1 Cl3 110.7(4) . .
Cl1 C1 Cl2 111.2(4) . .
Cl3 C1 Cl2 106.9(3) . .
Cl1 C1 H1 109.3 . .
Cl3 C1 H1 109.3 . .
Cl2 C1 H1 109.3 . .
Cl1A C1A Cl2A 111.1(9) . .
Cl1A C1A Cl3A 110.3(9) . .
Cl2A C1A Cl3A 109.1(9) . .
Cl1A C1A H1A 108.8 . .
Cl2A C1A H1A 108.8 . .
Cl3A C1A H1A 108.8 . .
Cl3B C1B Cl1B 125(2) . .
Cl3B C1B Cl2B 117.3(15) . .
Cl1B C1B Cl2B 103.9(16) . .
Cl3B C1B H1B 102.6 . .
Cl1B C1B H1B 102.6 . .
Cl2B C1B H1B 102.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 O2 1.975(3) .
Pd1 O1 1.991(3) .
Pd1 N11 2.004(3) .
Pd1 N21 2.014(3) .
N11 C16 1.339(5) .
N11 C12 1.353(5) .
C12 C13 1.373(6) .
C12 H12 0.9500 .
C13 C14 1.376(6) .
C13 H13 0.9500 .
C14 C15 1.391(6) .
C14 H14 0.9500 .
C15 C16 1.383(6) .
C15 H15 0.9500 .
C16 C17 1.542(5) .
C17 O1 1.396(4) 2_655
C17 O1 1.396(4) .
C17 C16 1.542(5) 2_655
N21 C26 1.353(5) .
N21 C22 1.353(5) .
C22 C23 1.374(6) .
C22 H22 0.9500 .
C23 C24 1.377(7) .
C23 H23 0.9500 .
C24 C25 1.378(7) .
C24 H24 0.9500 .
C25 C26 1.415(6) .
C25 H25 0.9500 .
C26 C36 1.474(6) .
C31 O2 1.310(5) .
C31 C36 1.415(6) .
C31 C32 1.422(6) .
C32 C33 1.352(6) .
C32 H32 0.9500 .
C33 F1 1.377(5) .
C33 C34 1.394(7) .
C34 C35 1.371(6) .
C34 H34 0.9500 .
C35 C36 1.402(6) .
C35 H35 0.9500 .
C1 Cl1 1.739(5) .
C1 Cl3 1.764(5) .
C1 Cl2 1.765(6) .
C1 H1 1.0000 .
C1A Cl1A 1.755(9) .
C1A Cl2A 1.756(9) .
C1A Cl3A 1.757(9) .
C1A H1A 1.0000 .
C1B Cl3B 1.49(3) .
C1B Cl1B 1.753(9) .
C1B Cl2B 1.88(4) .
C1B H1B 1.0000 .
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_4
O2 Pd1 N11 C16 173.8(3) . .
O1 Pd1 N11 C16 -7.1(3) . .
O2 Pd1 N11 C12 -11.5(4) . .
O1 Pd1 N11 C12 167.5(4) . .
C16 N11 C12 C13 -0.3(6) . .
Pd1 N11 C12 C13 -174.7(3) . .
N11 C12 C13 C14 -0.4(7) . .
C12 C13 C14 C15 0.9(7) . .
C13 C14 C15 C16 -0.7(7) . .
C12 N11 C16 C15 0.5(6) . .
Pd1 N11 C16 C15 175.4(3) . .
C12 N11 C16 C17 -178.1(4) . .
Pd1 N11 C16 C17 -3.2(5) . .
C14 C15 C16 N11 0.0(7) . .
C14 C15 C16 C17 178.5(4) . .
N11 C16 C17 O1 136.5(3) . 2_655
C15 C16 C17 O1 -42.0(6) . 2_655
N11 C16 C17 O1 16.6(5) . .
C15 C16 C17 O1 -162.0(4) . .
N11 C16 C17 C16 -103.3(4) . 2_655
C15 C16 C17 C16 78.1(4) . 2_655
O1 C17 O1 Pd1 -141.9(2) 2_655 .
C16 C17 O1 Pd1 -22.2(4) . .
C16 C17 O1 Pd1 98.0(3) 2_655 .
N11 Pd1 O1 C17 17.1(2) . .
N21 Pd1 O1 C17 -162.0(2) . .
O2 Pd1 N21 C26 17.7(3) . .
O1 Pd1 N21 C26 -161.4(3) . .
O2 Pd1 N21 C22 -155.0(3) . .
O1 Pd1 N21 C22 25.9(3) . .
C26 N21 C22 C23 -2.0(7) . .
Pd1 N21 C22 C23 171.0(4) . .
N21 C22 C23 C24 -0.8(8) . .
C22 C23 C24 C25 1.5(8) . .
C23 C24 C25 C26 0.4(8) . .
C22 N21 C26 C25 3.8(6) . .
Pd1 N21 C26 C25 -168.6(3) . .
C22 N21 C26 C36 -177.7(4) . .
Pd1 N21 C26 C36 9.9(6) . .
C24 C25 C26 N21 -3.1(7) . .
C24 C25 C26 C36 178.4(5) . .
O2 C31 C32 C33 -179.9(4) . .
C36 C31 C32 C33 -2.3(6) . .
C31 C32 C33 F1 179.5(4) . .
C31 C32 C33 C34 -2.4(7) . .
C32 C33 C34 C35 4.1(7) . .
F1 C33 C34 C35 -177.8(4) . .
C33 C34 C35 C36 -1.1(7) . .
C34 C35 C36 C31 -3.4(7) . .
C34 C35 C36 C26 171.7(4) . .
O2 C31 C36 C35 -177.7(4) . .
C32 C31 C36 C35 5.0(6) . .
O2 C31 C36 C26 7.5(6) . .
C32 C31 C36 C26 -169.8(4) . .
N21 C26 C36 C35 155.6(4) . .
C25 C26 C36 C35 -26.0(6) . .
N21 C26 C36 C31 -29.6(6) . .
C25 C26 C36 C31 148.8(4) . .
C36 C31 O2 Pd1 30.5(5) . .
C32 C31 O2 Pd1 -152.1(3) . .
N11 Pd1 O2 C31 143.6(3) . .
N21 Pd1 O2 C31 -37.3(3) . .
