#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/70/2217088.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_2217088
loop_
_publ_author_name
'Nelana, Simphiwe M.'
'Kruger, Gert J.'
'Darkwa, James'
_publ_section_title
Dichlorido(3,5-dimethyl-1H-pyrazole)[(3,5-dimethyl-1H-pyrazol-1-yl)(o-tolyl)methanone]palladium(II)
_journal_coeditor_code           HB2672
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m206
_journal_page_last               m207
_journal_paper_doi               10.1107/S1600536807066627
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Pd Cl2 (C5 H8 N2) (C12 H12 N2 O)]'
_chemical_formula_moiety         'C18 H22 Cl2 N4 O Pd'
_chemical_formula_sum            'C18 H22 Cl2 N4 O Pd'
_chemical_formula_weight         487.70
_chemical_name_systematic
Dichlorido(3,5-dimethyl-1H-pyrazole)[(3,5-dimethyl-1H-pyrazol-1-yl)(o-tolyl)methanone]palladium(II)
_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            8
_cell_length_a                   15.908(3)
_cell_length_b                   15.479(3)
_cell_length_c                   16.602(3)
_cell_measurement_reflns_used    2686
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.21
_cell_volume                     4088.1(13)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART-NT (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
WinGX (Farrugia, 1999), PLATON (Spek, 2003) and publCIF
(Westrip, 2008)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 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  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43509
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.183
_exptl_absorpt_correction_T_max  0.8425
_exptl_absorpt_correction_T_min  0.7033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.093
_refine_diff_density_min         -0.493
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0398
_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)+(0.0425P)²+9.9045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                2686
_reflns_number_total             4023
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2672.cif
_cod_data_source_block           I
_cod_original_cell_volume        4088.0(12)
_cod_database_code               2217088
_cod_database_fobs_code          2217088
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
C C11 0.1260(3) -0.2107(3) 0.4805(3) 0.0544(13) Uani d . 1
C C12 0.1495(4) -0.2290(3) 0.4037(4) 0.0588(14) Uani d . 1
H H12 0.1646 -0.2829 0.3836 0.071 Uiso calc R 1
C C13 0.1468(4) -0.1521(3) 0.3608(3) 0.0551(13) Uani d . 1
C C14 0.1168(4) -0.2659(4) 0.5543(4) 0.087(2) Uani d . 1
H H14A 0.1677 -0.2977 0.5631 0.130 Uiso calc R 1
H H14B 0.0709 -0.3054 0.5470 0.130 Uiso calc R 1
H H14C 0.1057 -0.2297 0.6001 0.130 Uiso calc R 1
C C15 0.1668(5) -0.1341(4) 0.2743(4) 0.095(2) Uani d . 1
H H15A 0.1195 -0.1067 0.2491 0.142 Uiso calc R 1
H H15B 0.1791 -0.1874 0.2472 0.142 Uiso calc R 1
H H15C 0.2148 -0.0966 0.2712 0.142 Uiso calc R 1
C C21 0.1020(4) 0.3084(3) 0.3533(4) 0.0726(18) Uani d . 1
C C22 0.1203(4) 0.3102(4) 0.4313(4) 0.0668(16) Uani d . 1
H H22 0.1299 0.3593 0.4623 0.080 Uiso calc R 1
C C23 0.1226(4) 0.2247(3) 0.4582(3) 0.0580(14) Uani d . 1
C C24 0.0921(6) 0.3799(4) 0.2929(5) 0.115(3) Uani d . 1
H H24A 0.0338 0.3952 0.2886 0.173 Uiso calc R 1
H H24B 0.1122 0.3608 0.2414 0.173 Uiso calc R 1
H H24C 0.1238 0.4293 0.3100 0.173 Uiso calc R 1
C C25 0.1364(5) 0.1919(4) 0.5424(4) 0.095(2) Uani d . 1
H H25A 0.0850 0.1676 0.5626 0.142 Uiso calc R 1
H H25B 0.1536 0.2388 0.5764 0.142 Uiso calc R 1
H H25C 0.1793 0.1483 0.5419 0.142 Uiso calc R 1
C C26 0.0658(4) 0.1895(4) 0.2552(3) 0.0679(16) Uani d . 1
C C32 0.2068(4) 0.1314(4) 0.2339(4) 0.0711(17) Uani d . 1
H H32 0.2248 0.1655 0.2767 0.085 Uiso calc R 1
C C31 0.1223(3) 0.1290(3) 0.2129(3) 0.0495(12) Uani d . 1
C C33 0.2646(4) 0.0820(5) 0.1902(4) 0.086(2) Uani d . 1
H H33 0.3213 0.0829 0.2038 0.103 Uiso calc R 1
C C34 0.2379(5) 0.0334(5) 0.1288(4) 0.085(2) Uani d . 1
H H34 0.2763 0.0012 0.0992 0.102 Uiso calc R 1
C C35 0.1495(5) 0.0305(4) 0.1079(3) 0.0738(18) Uani d . 1
H H35 0.1312 -0.0047 0.0659 0.089 Uiso calc R 1
C C36 0.0945(4) 0.0783(4) 0.1488(3) 0.0687(17) Uani d . 1
C C37 0.0019(5) 0.0762(5) 0.1242(4) 0.093(2) Uani d . 1
H H37B -0.0105 0.1254 0.0910 0.140 Uiso calc R 1
H H37C -0.0328 0.0776 0.1715 0.140 Uiso calc R 1
H H37A -0.0092 0.0242 0.0945 0.140 Uiso calc R 1
N N11 0.1224(3) -0.0881(3) 0.4099(2) 0.0491(10) Uani d . 1
N N12 0.1103(3) -0.1256(3) 0.4824(2) 0.0521(10) Uani d . 1
H H12A 0.0943 -0.0982 0.5248 0.062 Uiso calc R 1
N N21 0.1115(2) 0.1715(2) 0.3970(2) 0.0425(9) Uani d . 1
N N22 0.0961(3) 0.2227(3) 0.3322(3) 0.0650(13) Uani d . 1
O O1 0.0029(4) 0.2206(3) 0.2275(3) 0.1102(19) Uani d . 1
Cl Cl1 0.25848(9) 0.04521(9) 0.42155(10) 0.0660(4) Uani d . 1
Cl Cl2 -0.02466(9) 0.02924(9) 0.36848(9) 0.0614(4) Uani d . 1
Pd Pd1 0.11619(2) 0.03965(2) 0.39821(2) 0.04292(14) Uani 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'
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
_geom_angle_publ_flag
N12 C11 C12 106.2(5) ?
N12 C11 C14 121.3(5) ?
C12 C11 C14 132.5(5) ?
C11 C12 C13 107.1(5) ?
C11 C12 H12 126.5 ?
C13 C12 H12 126.5 ?
N11 C13 C12 109.3(5) ?
N11 C13 C15 120.5(5) ?
C12 C13 C15 130.1(5) ?
C11 C14 H14A 109.5 ?
C11 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C11 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C13 C15 H15A 109.5 ?
C13 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C13 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C22 C21 N22 106.5(5) ?
C22 C21 C24 131.2(6) ?
N22 C21 C24 122.2(6) ?
C21 C22 C23 107.3(5) ?
C21 C22 H22 126.3 ?
C23 C22 H22 126.3 ?
N21 C23 C22 110.0(5) ?
N21 C23 C25 121.6(5) ?
C22 C23 C25 128.4(5) ?
C21 C24 H24A 109.5 ?
C21 C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
C21 C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
C23 C25 H25A 109.5 ?
C23 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
C23 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
O1 C26 N22 117.9(5) ?
O1 C26 C31 125.4(6) ?
N22 C26 C31 116.0(5) ?
C31 C32 C33 119.4(6) ?
C31 C32 H32 120.3 ?
C33 C32 H32 120.3 ?
C32 C31 C36 120.9(5) ?
C32 C31 C26 117.0(5) ?
C36 C31 C26 121.7(5) ?
C34 C33 C32 119.6(7) ?
C34 C33 H33 120.2 ?
C32 C33 H33 120.2 ?
C33 C34 C35 120.6(6) ?
C33 C34 H34 119.7 ?
C35 C34 H34 119.7 ?
C36 C35 C34 119.8(6) ?
C36 C35 H35 120.1 ?
C34 C35 H35 120.1 ?
C35 C36 C31 119.6(7) ?
C35 C36 C37 118.9(6) ?
C31 C36 C37 121.5(6) ?
C36 C37 H37B 109.5 ?
C36 C37 H37C 109.5 ?
H37B C37 H37C 109.5 ?
C36 C37 H37A 109.5 ?
H37B C37 H37A 109.5 ?
H37C C37 H37A 109.5 ?
C13 N11 N12 105.4(4) ?
C13 N11 Pd1 133.6(3) ?
N12 N11 Pd1 120.5(3) ?
C11 N12 N11 112.0(4) ?
C11 N12 H12A 124.0 ?
N11 N12 H12A 124.0 ?
C23 N21 N22 105.7(4) ?
C23 N21 Pd1 127.7(3) ?
N22 N21 Pd1 126.6(3) ?
N21 N22 C21 110.4(4) ?
N21 N22 C26 123.3(4) ?
C21 N22 C26 125.8(5) ?
N11 Pd1 N21 174.88(15) y
N11 Pd1 Cl1 88.39(13) y
N21 Pd1 Cl1 90.02(12) y
N11 Pd1 Cl2 89.98(13) y
N21 Pd1 Cl2 91.84(12) y
Cl1 Pd1 Cl2 176.71(5) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C11 N12 1.342(6) ?
C11 C12 1.358(8) ?
C11 C14 1.501(8) ?
C12 C13 1.388(7) ?
C12 H12 0.9300 ?
C13 N11 1.340(6) ?
C13 C15 1.498(8) ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C21 C22 1.328(9) ?
C21 N22 1.377(7) ?
C21 C24 1.501(8) ?
C22 C23 1.398(8) ?
C22 H22 0.9300 ?
C23 N21 1.319(6) ?
C23 C25 1.503(8) ?
C24 H24A 0.9600 ?
C24 H24B 0.9600 ?
C24 H24C 0.9600 ?
C25 H25A 0.9600 ?
C25 H25B 0.9600 ?
C25 H25C 0.9600 ?
C26 O1 1.202(7) ?
C26 N22 1.459(7) ?
C26 C31 1.475(7) ?
C32 C31 1.389(8) ?
C32 C33 1.398(8) ?
C32 H32 0.9300 ?
C31 C36 1.394(8) ?
C33 C34 1.336(10) ?
C33 H33 0.9300 ?
C34 C35 1.449(10) ?
C34 H34 0.9300 ?
C35 C36 1.333(8) ?
C35 H35 0.9300 ?
C36 C37 1.529(9) ?
C37 H37B 0.9600 ?
C37 H37C 0.9600 ?
C37 H37A 0.9600 ?
N11 N12 1.350(5) ?
Pd1 N11 1.989(4) yes
Pd1 N21 2.042(4) yes
Pd1 Cl1 2.2981(15) yes
Pd1 Cl2 2.3001(15) yes
N12 H12A 0.8600 ?
N21 N22 1.359(5) ?
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
N12 H12A Cl2 5_556 0.86 2.35 3.194(4) 169
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_publ_flag
N12 C11 C12 C13 -0.2(6) ?
C14 C11 C12 C13 -179.9(6) ?
C11 C12 C13 N11 0.1(7) ?
C11 C12 C13 C15 179.5(7) ?
N22 C21 C22 C23 -2.1(7) ?
C24 C21 C22 C23 -179.4(7) ?
C21 C22 C23 N21 4.1(7) ?
C21 C22 C23 C25 -176.7(7) ?
C33 C32 C31 C36 -0.2(8) ?
C33 C32 C31 C26 -173.4(6) ?
O1 C26 C31 C32 149.9(7) n
N22 C26 C31 C32 -21.1(7) ?
O1 C26 C31 C36 -23.3(10) ?
N22 C26 C31 C36 165.7(5) ?
C31 C32 C33 C34 0.2(10) ?
C32 C33 C34 C35 -0.9(11) ?
C33 C34 C35 C36 1.7(10) ?
C34 C35 C36 C31 -1.7(9) ?
C34 C35 C36 C37 178.3(6) ?
C32 C31 C36 C35 1.0(8) ?
C26 C31 C36 C35 173.9(5) ?
C32 C31 C36 C37 -179.0(5) ?
C26 C31 C36 C37 -6.1(8) ?
C12 C13 N11 N12 0.0(6) ?
C15 C13 N11 N12 -179.5(6) ?
C12 C13 N11 Pd1 171.6(4) ?
C15 C13 N11 Pd1 -7.9(9) ?
C12 C11 N12 N11 0.2(6) ?
C14 C11 N12 N11 180.0(5) ?
C13 N11 N12 C11 -0.1(6) ?
Pd1 N11 N12 C11 -173.1(3) ?
C22 C23 N21 N22 -4.3(6) ?
C25 C23 N21 N22 176.5(6) ?
C22 C23 N21 Pd1 175.7(4) ?
C25 C23 N21 Pd1 -3.5(8) ?
C23 N21 N22 C21 3.0(6) ?
Pd1 N21 N22 C21 -177.0(4) ?
C23 N21 N22 C26 -168.9(5) ?
Pd1 N21 N22 C26 11.1(7) ?
C22 C21 N22 N21 -0.5(7) ?
C24 C21 N22 N21 177.0(6) ?
C22 C21 N22 C26 171.1(6) ?
C24 C21 N22 C26 -11.3(11) ?
O1 C26 N22 N21 125.6(7) n
C31 C26 N22 N21 -62.7(7) ?
O1 C26 N22 C21 -45.1(10) ?
C31 C26 N22 C21 126.6(6) ?
C13 N11 Pd1 Cl1 -79.2(5) ?
N12 N11 Pd1 Cl1 91.4(3) n
C13 N11 Pd1 Cl2 97.9(5) ?
N12 N11 Pd1 Cl2 -91.5(3) ?
C23 N21 Pd1 Cl1 -68.9(4) ?
N22 N21 Pd1 Cl1 111.1(4) n
C23 N21 Pd1 Cl2 113.8(4) ?
N22 N21 Pd1 Cl2 -66.2(4) ?
