#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/60/2236014.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_2236014
loop_
_publ_author_name
'Warsink, Stefan'
'Roodt, Andreas'
_publ_section_title
;
 trans-Bis[1-(2-benzamidoethyl)-3-(2,4,6-trimethylphenyl)imidazol-2-ylidene]dichloridopalladium(II)
;
_journal_coeditor_code           WM2660
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1075
_journal_page_last               m1076
_journal_paper_doi               10.1107/S1600536812031868
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Pd Cl2 (C21 H23 N3 O)2]'
_chemical_formula_moiety         'C42 H46 Cl2 N6 O2 Pd'
_chemical_formula_sum            'C42 H46 Cl2 N6 O2 Pd'
_chemical_formula_weight         844.15
_chemical_name_systematic
;
trans-Bis[1-(2-benzamidoethyl)-3-(2,4,6-trimethylphenyl)imidazol-
2-ylidene]dichloridopalladium(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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.000
_cell_angle_beta                 113.3098(10)
_cell_angle_gamma                90.000
_cell_formula_units_Z            2
_cell_length_a                   12.594(4)
_cell_length_b                   11.736(4)
_cell_length_c                   14.403(4)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.47
_cell_volume                     1955.1(11)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 APEXII KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28432
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.426
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0208
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0252P)²+1.2060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0553
_reflns_number_gt                4441
_reflns_number_total             4845
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            wm2660.cif
_cod_data_source_block           I
_cod_original_cell_volume        1955.0(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236014
_cod_database_fobs_code          2236014
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
C C01 0.93466(11) 0.12682(11) 0.89676(9) 0.0151(2) Uani d . 1
C C02 0.83145(13) 0.21976(12) 0.75160(10) 0.0225(3) Uani d . 1
H H02 0.7778 0.2338 0.6844 0.027 Uiso calc R 1
C C03 0.90016(13) 0.29692(13) 0.81658(10) 0.0237(3) Uani d . 1
H H03 0.905 0.3758 0.8041 0.028 Uiso calc R 1
C C04 0.79774(13) 0.00921(12) 0.75366(10) 0.0195(3) Uani d . 1
H H04A 0.855 -0.0393 0.7411 0.023 Uiso calc R 1
H H04B 0.7351 0.0269 0.6874 0.023 Uiso calc R 1
C C05 0.74689(12) -0.05763(12) 0.81778(10) 0.0204(3) Uani d . 1
H H05A 0.687 -0.1103 0.7731 0.025 Uiso calc R 1
H H05B 0.8089 -0.1045 0.8673 0.025 Uiso calc R 1
C C06 0.60980(12) 0.08742(13) 0.82388(10) 0.0207(3) Uani d . 1
C C07 0.57994(12) 0.16735(13) 0.89085(10) 0.0204(3) Uani d . 1
C C08 0.54646(13) 0.27752(14) 0.85645(11) 0.0269(3) Uani d . 1
H H08 0.5419 0.2997 0.7915 0.032 Uiso calc R 1
C C09 0.51965(15) 0.35543(15) 0.91642(13) 0.0336(4) Uani d . 1
H H09 0.4984 0.4312 0.8932 0.04 Uiso calc R 1
C C10 0.52404(14) 0.32240(17) 1.01020(12) 0.0345(4) Uani d . 1
H H10 0.5057 0.3756 1.0513 0.041 Uiso calc R 1
C C11 0.55517(13) 0.21202(16) 1.04414(11) 0.0305(4) Uani d . 1
H H11 0.5565 0.1894 1.1079 0.037 Uiso calc R 1
C C12 0.58435(12) 0.13441(14) 0.98548(10) 0.0240(3) Uani d . 1
H H12 0.6072 0.0592 1.0096 0.029 Uiso calc R 1
C C13 1.04514(12) 0.29318(11) 0.99505(9) 0.0169(2) Uani d . 1
C C14 1.16210(12) 0.29244(11) 1.01144(10) 0.0189(3) Uani d . 1
C C15 1.23975(12) 0.34349(12) 1.09968(11) 0.0205(3) Uani d . 1
H H15 1.3197 0.3448 1.1123 0.025 Uiso calc R 1
C C16 1.20260(12) 0.39272(12) 1.16990(10) 0.0201(3) Uani d . 1
C C17 1.08462(12) 0.39442(11) 1.14869(10) 0.0191(3) Uani d . 1
H H17 1.0589 0.4282 1.1961 0.023 Uiso calc R 1
C C18 1.00316(12) 0.34792(11) 1.05991(10) 0.0175(3) Uani d . 1
C C19 1.20317(13) 0.23864(13) 0.93643(11) 0.0254(3) Uani d . 1
H H19A 1.2861 0.253 0.9574 0.038 Uiso calc R 1
H H19B 1.1608 0.2717 0.8693 0.038 Uiso calc R 1
H H19C 1.1893 0.1563 0.9339 0.038 Uiso calc R 1
C C20 1.28891(13) 0.44417(14) 1.26630(11) 0.0269(3) Uani d . 1
H H20A 1.2478 0.4878 1.2998 0.04 Uiso calc R 1
H H20B 1.3412 0.4948 1.2503 0.04 Uiso calc R 1
H H20C 1.3337 0.3833 1.3113 0.04 Uiso calc R 1
C C21 0.87535(12) 0.36035(12) 1.03310(10) 0.0212(3) Uani d . 1
H H21A 0.863 0.3995 1.0881 0.032 Uiso calc R 1
H H21B 0.8395 0.2847 1.023 0.032 Uiso calc R 1
H H21C 0.8404 0.4049 0.9708 0.032 Uiso calc R 1
N N1 0.85384(10) 0.11576(10) 0.80130(8) 0.0165(2) Uani d . 1
N N2 0.96271(10) 0.23883(9) 0.90550(8) 0.0167(2) Uani d . 1
N N3 0.69588(11) 0.01305(10) 0.87193(9) 0.0197(2) Uani d . 1
O O1 0.55957(10) 0.09075(10) 0.73122(7) 0.0289(2) Uani d . 1
Cl Cl1 1.09679(3) -0.06511(3) 0.90286(2) 0.01787(7) Uani d . 1
Pd Pd1 1 0 1 0.01239(4) Uani d S 1
H H1 0.7338(16) 0.0244(15) 0.9304(15) 0.023(4) 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 0 '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 0.006 '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
_geom_angle_publ_flag
N2 C01 N1 . . 104.54(11) ?
N2 C01 Pd1 . . 128.86(10) ?
N1 C01 Pd1 . . 126.59(10) ?
C03 C02 N1 . . 106.89(12) ?
C03 C02 H02 . . 126.6 ?
N1 C02 H02 . . 126.6 ?
C02 C03 N2 . . 106.60(13) ?
C02 C03 H03 . . 126.7 ?
N2 C03 H03 . . 126.7 ?
N1 C04 C05 . . 113.17(11) ?
N1 C04 H04A . . 108.9 ?
C05 C04 H04A . . 108.9 ?
N1 C04 H04B . . 108.9 ?
C05 C04 H04B . . 108.9 ?
H04A C04 H04B . . 107.8 ?
N3 C05 C04 . . 114.26(12) ?
N3 C05 H05A . . 108.7 ?
C04 C05 H05A . . 108.7 ?
N3 C05 H05B . . 108.7 ?
C04 C05 H05B . . 108.7 ?
H05A C05 H05B . . 107.6 ?
O1 C06 N3 . . 122.72(14) ?
O1 C06 C07 . . 121.78(13) ?
N3 C06 C07 . . 115.50(12) ?
C08 C07 C12 . . 119.67(14) ?
C08 C07 C06 . . 118.15(13) ?
C12 C07 C06 . . 122.18(14) ?
C09 C08 C07 . . 120.36(15) ?
C09 C08 H08 . . 119.8 ?
C07 C08 H08 . . 119.8 ?
C10 C09 C08 . . 119.78(16) ?
C10 C09 H09 . . 120.1 ?
C08 C09 H09 . . 120.1 ?
C09 C10 C11 . . 120.16(15) ?
C09 C10 H10 . . 119.9 ?
C11 C10 H10 . . 119.9 ?
C10 C11 C12 . . 120.35(15) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C11 C12 C07 . . 119.66(15) ?
C11 C12 H12 . . 120.2 ?
C07 C12 H12 . . 120.2 ?
C14 C13 C18 . . 122.83(12) ?
C14 C13 N2 . . 119.03(12) ?
C18 C13 N2 . . 118.10(12) ?
C15 C14 C13 . . 117.61(12) ?
C15 C14 C19 . . 121.11(13) ?
C13 C14 C19 . . 121.28(12) ?
C14 C15 C16 . . 121.50(14) ?
C14 C15 H15 . . 119.3 ?
C16 C15 H15 . . 119.3 ?
C17 C16 C15 . . 118.74(13) ?
C17 C16 C20 . . 120.87(13) ?
C15 C16 C20 . . 120.39(13) ?
C16 C17 C18 . . 121.92(13) ?
C16 C17 H17 . . 119 ?
C18 C17 H17 . . 119 ?
C17 C18 C13 . . 117.17(13) ?
C17 C18 C21 . . 121.37(12) ?
C13 C18 C21 . . 121.42(12) ?
C14 C19 H19A . . 109.5 ?
C14 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C14 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C16 C20 H20A . . 109.5 ?
C16 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C16 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C18 C21 H21A . . 109.5 ?
C18 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C18 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C01 N1 C02 . . 110.93(12) ?
C01 N1 C04 . . 125.88(11) ?
C02 N1 C04 . . 123.18(11) ?
C01 N2 C03 . . 111.05(11) ?
C01 N2 C13 . . 125.47(11) ?
C03 N2 C13 . . 123.48(12) ?
C06 N3 C05 . . 122.04(12) ?
C06 N3 H1 . . 117.2(13) ?
C05 N3 H1 . . 117.1(13) ?
C01 Pd1 C01 3_757 . 180 ?
C01 Pd1 Cl1 3_757 . 92.45(4) ?
C01 Pd1 Cl1 . . 87.55(4) y
C01 Pd1 Cl1 3_757 3_757 87.55(4) ?
C01 Pd1 Cl1 . 3_757 92.45(4) ?
Cl1 Pd1 Cl1 . 3_757 180 ?
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
C01 N2 . 1.3541(18) ?
C01 N1 . 1.3548(16) ?
C01 Pd1 . 2.0335(14) y
C02 C03 . 1.343(2) ?
C02 N1 . 1.3864(18) ?
C02 H02 . 0.95 ?
C03 N2 . 1.3882(17) ?
C03 H03 . 0.95 ?
C04 N1 . 1.4663(18) ?
C04 C05 . 1.532(2) ?
C04 H04A . 0.99 ?
C04 H04B . 0.99 ?
C05 N3 . 1.4512(19) ?
C05 H05A . 0.99 ?
C05 H05B . 0.99 ?
C06 O1 . 1.2307(17) ?
C06 N3 . 1.3498(19) ?
C06 C07 . 1.496(2) ?
C07 C08 . 1.389(2) ?
C07 C12 . 1.3965(19) ?
C08 C09 . 1.388(2) ?
C08 H08 . 0.95 ?
C09 C10 . 1.385(3) ?
C09 H09 . 0.95 ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.387(2) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C13 C14 . 1.397(2) ?
C13 C18 . 1.3985(19) ?
C13 N2 . 1.4451(17) ?
C14 C15 . 1.395(2) ?
C14 C19 . 1.5085(19) ?
C15 C16 . 1.396(2) ?
C15 H15 . 0.95 ?
C16 C17 . 1.394(2) ?
C16 C20 . 1.510(2) ?
C17 C18 . 1.3955(19) ?
C17 H17 . 0.95 ?
C18 C21 . 1.506(2) ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
N3 H1 . 0.797(19) ?
Cl1 Pd1 . 2.3188(6) y
Pd1 C01 3_757 2.0335(14) ?
Pd1 Cl1 3_757 2.3188(6) ?
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
N3 H1 Cl1 3_757 0.797(19) 2.549(19) 3.3181(15) 162.6(17)
C09 H09 O1 2_656 0.95 2.49 3.386(2) 156.5
C10 H10 O1 4_566 0.95 2.44 3.201(2) 137.4
C19 H19C Cl1 . 0.98 2.81 3.772(2) 166.9
C21 H21B Cl1 3_757 0.98 2.78 3.567(2) 137.3
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_4
_geom_torsion
N1 C02 C03 N2 . -0.59(16)
N1 C04 C05 N3 . 37.27(16)
O1 C06 C07 C08 . -34.5(2)
N3 C06 C07 C08 . 144.81(14)
O1 C06 C07 C12 . 145.30(15)
N3 C06 C07 C12 . -35.44(19)
C12 C07 C08 C09 . 1.3(2)
C06 C07 C08 C09 . -178.98(14)
C07 C08 C09 C10 . -1.3(2)
C08 C09 C10 C11 . 0.1(3)
C09 C10 C11 C12 . 1.3(2)
C10 C11 C12 C07 . -1.3(2)
C08 C07 C12 C11 . 0.1(2)
C06 C07 C12 C11 . -179.70(13)
C18 C13 C14 C15 . 3.7(2)
N2 C13 C14 C15 . -178.65(12)
C18 C13 C14 C19 . -176.21(13)
N2 C13 C14 C19 . 1.47(19)
C13 C14 C15 C16 . 0.6(2)
C19 C14 C15 C16 . -179.50(13)
C14 C15 C16 C17 . -2.6(2)
C14 C15 C16 C20 . 178.11(13)
C15 C16 C17 C18 . 0.4(2)
C20 C16 C17 C18 . 179.69(13)
C16 C17 C18 C13 . 3.61(19)
C16 C17 C18 C21 . -173.97(13)
C14 C13 C18 C17 . -5.72(19)
N2 C13 C18 C17 . 176.58(11)
C14 C13 C18 C21 . 171.86(12)
N2 C13 C18 C21 . -5.84(19)
N2 C01 N1 C02 . -0.38(15)
Pd1 C01 N1 C02 . -178.84(10)
N2 C01 N1 C04 . 178.29(12)
Pd1 C01 N1 C04 . -0.18(19)
C03 C02 N1 C01 . 0.62(16)
C03 C02 N1 C04 . -178.08(13)
C05 C04 N1 C01 . 51.09(18)
C05 C04 N1 C02 . -130.40(14)
N1 C01 N2 C03 . 0.00(15)
Pd1 C01 N2 C03 . 178.42(10)
N1 C01 N2 C13 . 179.11(12)
Pd1 C01 N2 C13 . -2.47(19)
C02 C03 N2 C01 . 0.38(17)
C02 C03 N2 C13 . -178.75(13)
C14 C13 N2 C01 . 85.73(17)
C18 C13 N2 C01 . -96.48(16)
C14 C13 N2 C03 . -95.26(16)
C18 C13 N2 C03 . 82.53(17)
O1 C06 N3 C05 . 9.0(2)
C07 C06 N3 C05 . -170.29(12)
C04 C05 N3 C06 . 57.45(18)
N2 C01 Pd1 Cl1 . -106.64(12)
N1 C01 Pd1 Cl1 . 71.46(11)
N2 C01 Pd1 Cl1 3_757 73.36(12)
N1 C01 Pd1 Cl1 3_757 -108.54(11)
