#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/96/2229639.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_2229639
loop_
_publ_author_name
'Lee, Hon Man'
'Chang, Yu-Chuan'
_publ_section_title
;
 trans-Bis[1-(2-anilino-2-oxoethyl)-3-benzyl-1H-imidazol-2-yl]palladium(II)
 methanol disolvate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m467
_journal_paper_doi               10.1107/S1600536811007768
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Pd (C18 H16 N3 O)2], 2C H4 O'
_chemical_formula_moiety         'C36 H32 N6 O2 Pd, 2(C H4 O)'
_chemical_formula_sum            'C38 H40 N6 O4 Pd'
_chemical_formula_weight         751.16
_chemical_name_systematic
;
trans-Bis[1-(2-anilino-2-oxoethyl)-3-benzyl-1H-
imidazol-2-yl]palladium(II) methanol disolvate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.822(2)
_cell_length_b                   9.0616(11)
_cell_length_c                   21.473(3)
_cell_measurement_reflns_used    3616
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.4
_cell_measurement_theta_min      2.7
_cell_volume                     3467.8(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            45827
_diffrn_reflns_theta_full        28.65
_diffrn_reflns_theta_max         28.65
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  0.9547
_exptl_absorpt_correction_T_min  0.8040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelpiped
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.668
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0322
_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)+(0.0273P)²+3.0876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0842
_reflns_number_gt                2695
_reflns_number_total             4451
_reflns_threshold_expression     I>2σ
_cod_data_source_file            fj2398.cif
_cod_data_source_block           I
_cod_original_cell_volume        3467.8(7)
_cod_database_code               2229639
_cod_database_fobs_code          2229639
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C C1 0.46400(13) 0.2896(2) 0.99551(11) 0.0171(5) Uani d . 1 . .
C C2 0.38152(15) 0.1075(3) 1.01712(12) 0.0228(6) Uani d . 1 . .
H H2 0.3418 0.0545 1.0363 0.027 Uiso calc R 1 . .
C C3 0.42383(14) 0.0630(3) 0.96912(13) 0.0226(6) Uani d . 1 . .
H H3 0.4198 -0.0284 0.9477 0.027 Uiso calc R 1 . .
C C4 0.52739(16) 0.1767(3) 0.90363(11) 0.0219(5) Uani d . 1 . .
H H4A 0.5339 0.0748 0.8879 0.026 Uiso calc R 1 . .
H H4B 0.5769 0.2124 0.9181 0.026 Uiso calc R 1 . .
C C5 0.49996(16) 0.2745(3) 0.85115(11) 0.0217(5) Uani d . 1 . .
C C6 0.42429(16) 0.2778(3) 0.83425(12) 0.0280(6) Uani d . 1 . .
H H6 0.3890 0.2191 0.8563 0.034 Uiso calc R 1 . .
C C7 0.40060(18) 0.3664(3) 0.78546(13) 0.0350(7) Uani d . 1 . .
H H7 0.3491 0.3676 0.7740 0.042 Uiso calc R 1 . .
C C8 0.45124(19) 0.4528(3) 0.75345(14) 0.0385(8) Uani d . 1 . .
H H8 0.4347 0.5133 0.7200 0.046 Uiso calc R 1 . .
C C9 0.5260(2) 0.4511(4) 0.77007(14) 0.0389(8) Uani d . 1 . .
H H9 0.5609 0.5111 0.7482 0.047 Uiso calc R 1 . .
C C10 0.55057(17) 0.3619(3) 0.81869(13) 0.0300(6) Uani d . 1 . .
H H10 0.6022 0.3608 0.8297 0.036 Uiso calc R 1 . .
C C11 0.37610(15) 0.3458(3) 1.07994(11) 0.0211(6) Uani d . 1 . .
H H11A 0.4153 0.3697 1.1110 0.025 Uiso calc R 1 . .
H H11B 0.3347 0.2947 1.1019 0.025 Uiso calc R 1 . .
C C12 0.34608(14) 0.4900(3) 1.05140(11) 0.0181(5) Uani d . 1 . .
C C13 0.35913(13) 0.6589(2) 0.96519(11) 0.0165(5) Uani d . 1 . .
C C14 0.39053(15) 0.6620(3) 0.90513(12) 0.0222(6) Uani d . 1 . .
H H14 0.4311 0.5979 0.8955 0.027 Uiso calc R 1 . .
C C15 0.36355(16) 0.7567(3) 0.85971(12) 0.0286(6) Uani d . 1 . .
H H15 0.3859 0.7576 0.8195 0.034 Uiso calc R 1 . .
C C16 0.30402(16) 0.8504(3) 0.87279(13) 0.0296(6) Uani d . 1 . .
H H16 0.2846 0.9140 0.8415 0.036 Uiso calc R 1 . .
C C17 0.27323(16) 0.8499(3) 0.93189(13) 0.0279(6) Uani d . 1 . .
H H17 0.2327 0.9145 0.9411 0.033 Uiso calc R 1 . .
C C18 0.30045(14) 0.7565(3) 0.97816(13) 0.0229(5) Uani d . 1 . .
H H18 0.2791 0.7592 1.0187 0.027 Uiso calc R 1 . .
C C19 0.2385(2) 0.1346(5) 0.70995(15) 0.0574(10) Uani d . 1 . .
H H19A 0.2522 0.2332 0.6950 0.086 Uiso calc R 1 . .
H H19B 0.2842 0.0770 0.7175 0.086 Uiso calc R 1 . .
H H19C 0.2100 0.1434 0.7488 0.086 Uiso calc R 1 . .
N N1 0.40758(11) 0.2469(2) 1.03309(9) 0.0182(4) Uani d . 1 . .
N N2 0.47490(12) 0.1753(2) 0.95629(9) 0.0184(4) Uani d . 1 . .
N N3 0.38849(11) 0.5529(2) 1.00742(9) 0.0174(4) Uani d . 1 . .
O O1 0.28388(10) 0.5348(2) 1.07073(8) 0.0254(4) Uani d . 1 . .
Pd Pd1 0.5000 0.5000 1.0000 0.01396(7) Uani d S 1 . .
O O2 0.19462(14) 0.0636(3) 0.66513(12) 0.0650(8) Uani d . 1 . .
H H1 0.2245 0.0384 0.6316 0.078 Uiso d . 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'
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'
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
N1 C1 N2 . . 105.1(2) ?
N1 C1 Pd1 . . 118.80(17) ?
N2 C1 Pd1 . . 135.30(18) ?
C3 C2 N1 . . 106.0(2) ?
C3 C2 H2 . . 127.0 ?
N1 C2 H2 . . 127.0 ?
C2 C3 N2 . . 107.5(2) ?
C2 C3 H3 . . 126.3 ?
N2 C3 H3 . . 126.3 ?
N2 C4 C5 . . 111.9(2) ?
N2 C4 H4A . . 109.2 ?
C5 C4 H4A . . 109.2 ?
N2 C4 H4B . . 109.2 ?
C5 C4 H4B . . 109.2 ?
H4A C4 H4B . . 107.9 ?
C10 C5 C6 . . 119.0(2) ?
C10 C5 C4 . . 119.9(3) ?
C6 C5 C4 . . 121.1(2) ?
C7 C6 C5 . . 120.2(3) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C8 C7 C6 . . 120.4(3) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C9 . . 119.8(3) ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
C8 C9 C10 . . 120.3(3) ?
C8 C9 H9 . . 119.8 ?
C10 C9 H9 . . 119.8 ?
C5 C10 C9 . . 120.2(3) ?
C5 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
N1 C11 C12 . . 112.36(19) ?
N1 C11 H11A . . 109.1 ?
C12 C11 H11A . . 109.1 ?
N1 C11 H11B . . 109.1 ?
C12 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.9 ?
O1 C12 N3 . . 126.6(2) ?
O1 C12 C11 . . 116.8(2) ?
N3 C12 C11 . . 116.5(2) ?
C18 C13 C14 . . 117.9(2) ?
C18 C13 N3 . . 125.2(2) ?
C14 C13 N3 . . 116.9(2) ?
C15 C14 C13 . . 121.3(2) ?
C15 C14 H14 . . 119.3 ?
C13 C14 H14 . . 119.3 ?
C14 C15 C16 . . 120.1(3) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C17 C16 C15 . . 119.2(3) ?
C17 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C16 C17 C18 . . 121.2(3) ?
C16 C17 H17 . . 119.4 ?
C18 C17 H17 . . 119.4 ?
C17 C18 C13 . . 120.2(3) ?
C17 C18 H18 . . 119.9 ?
C13 C18 H18 . . 119.9 ?
O2 C19 H19A . . 109.5 ?
O2 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O2 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C1 N1 C2 . . 111.3(2) ?
C1 N1 C11 . . 121.6(2) ?
C2 N1 C11 . . 126.9(2) ?
C1 N2 C3 . . 110.1(2) ?
C1 N2 C4 . . 124.5(2) ?
C3 N2 C4 . . 125.1(2) ?
C12 N3 C13 . . 122.0(2) ?
C12 N3 Pd1 . . 120.21(16) ?
C13 N3 Pd1 . . 117.74(15) ?
C1 Pd1 C1 5_667 . 179.9990(10) ?
C1 Pd1 N3 5_667 . 94.81(9) ?
C1 Pd1 N3 . . 85.19(9) ?
C1 Pd1 N3 5_667 5_667 85.19(9) ?
C1 Pd1 N3 . 5_667 94.81(9) ?
N3 Pd1 N3 . 5_667 179.9990(10) ?
C19 O2 H1 . . 109.1 ?
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
C1 N1 . 1.346(3) ?
C1 N2 . 1.349(3) ?
C1 Pd1 . 2.014(2) ?
C2 C3 . 1.339(4) ?
C2 N1 . 1.388(3) ?
C2 H2 . 0.9500 ?
C3 N2 . 1.393(3) ?
C3 H3 . 0.9500 ?
C4 N2 . 1.468(3) ?
C4 C5 . 1.515(3) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C10 . 1.388(4) ?
C5 C6 . 1.397(4) ?
C6 C7 . 1.386(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.378(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.379(5) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.391(4) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 N1 . 1.460(3) ?
C11 C12 . 1.540(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 O1 . 1.252(3) ?
C12 N3 . 1.337(3) ?
C13 C18 . 1.398(3) ?
C13 C14 . 1.406(3) ?
C13 N3 . 1.421(3) ?
C14 C15 . 1.385(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.387(4) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.383(4) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.392(4) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 O2 . 1.397(4) ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
N3 Pd1 . 2.050(2) ?
Pd1 C1 5_667 2.014(2) ?
Pd1 N3 5_667 2.051(2) ?
O2 H1 . 0.9244 ?
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
O2 H1 O1 7_565 0.92 1.81 2.727(3) 172
C2 H2 O1 8_655 0.95 2.36 3.232(3) 152
C18 H18 O1 . 0.95 2.32 2.842(3) 114
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C2 C3 N2 . . . . -0.1(3) ?
N2 C4 C5 C10 . . . . 140.4(2) ?
N2 C4 C5 C6 . . . . -40.1(3) ?
C10 C5 C6 C7 . . . . 0.5(4) ?
C4 C5 C6 C7 . . . . -179.0(2) ?
C5 C6 C7 C8 . . . . -0.4(4) ?
C6 C7 C8 C9 . . . . 0.0(5) ?
C7 C8 C9 C10 . . . . 0.4(5) ?
C6 C5 C10 C9 . . . . -0.1(4) ?
C4 C5 C10 C9 . . . . 179.4(2) ?
C8 C9 C10 C5 . . . . -0.4(4) ?
N1 C11 C12 O1 . . . . 136.3(2) ?
N1 C11 C12 N3 . . . . -42.3(3) ?
C18 C13 C14 C15 . . . . -1.1(4) ?
N3 C13 C14 C15 . . . . 177.1(2) ?
C13 C14 C15 C16 . . . . -0.5(4) ?
C14 C15 C16 C17 . . . . 1.3(4) ?
C15 C16 C17 C18 . . . . -0.5(4) ?
C16 C17 C18 C13 . . . . -1.1(4) ?
C14 C13 C18 C17 . . . . 1.9(4) ?
N3 C13 C18 C17 . . . . -176.1(2) ?
N2 C1 N1 C2 . . . . -1.3(3) ?
Pd1 C1 N1 C2 . . . . 170.12(17) ?
N2 C1 N1 C11 . . . . -176.1(2) ?
Pd1 C1 N1 C11 . . . . -4.7(3) ?
C3 C2 N1 C1 . . . . 0.9(3) ?
C3 C2 N1 C11 . . . . 175.4(2) ?
C12 C11 N1 C1 . . . . 57.6(3) ?
C12 C11 N1 C2 . . . . -116.4(3) ?
N1 C1 N2 C3 . . . . 1.2(3) ?
Pd1 C1 N2 C3 . . . . -168.1(2) ?
N1 C1 N2 C4 . . . . 175.0(2) ?
Pd1 C1 N2 C4 . . . . 5.7(4) ?
C2 C3 N2 C1 . . . . -0.7(3) ?
C2 C3 N2 C4 . . . . -174.4(2) ?
C5 C4 N2 C1 . . . . -71.5(3) ?
C5 C4 N2 C3 . . . . 101.4(3) ?
O1 C12 N3 C13 . . . . -16.9(4) ?
C11 C12 N3 C13 . . . . 161.5(2) ?
O1 C12 N3 Pd1 . . . . 162.1(2) ?
C11 C12 N3 Pd1 . . . . -19.5(3) ?
C18 C13 N3 C12 . . . . 30.0(4) ?
C14 C13 N3 C12 . . . . -148.0(2) ?
C18 C13 N3 Pd1 . . . . -149.0(2) ?
C14 C13 N3 Pd1 . . . . 32.9(3) ?
N1 C1 Pd1 N3 . . . . -40.62(19) ?
N2 C1 Pd1 N3 . . . . 127.6(3) ?
N1 C1 Pd1 N3 . . . 5_667 139.37(19) ?
N2 C1 Pd1 N3 . . . 5_667 -52.4(3) ?
C12 N3 Pd1 C1 . . . 5_667 -126.10(19) ?
C13 N3 Pd1 C1 . . . 5_667 52.97(18) ?
C12 N3 Pd1 C1 . . . . 53.90(19) ?
C13 N3 Pd1 C1 . . . . -127.03(18) ?
