#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/69/2216909.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_2216909
loop_
_publ_author_name
'Chun-Sen Liu'
'Guang-Hui Sun'
'Liang-Qi Guo'
_publ_section_title
Dichlorido[1-(1-naphthylmethyl)-3-(2-pyridyl)-1H-pyrazole-κ²N²,N³]palladium(II)
_journal_coeditor_code           BI2262
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m69
_journal_page_last               m69
_journal_paper_doi               10.1107/S1600536807062927
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Pd Cl2 (C19 H15 N3)]'
_chemical_formula_moiety         '[(C19 H15 N3) Pd Cl2]'
_chemical_formula_sum            'C19 H15 Cl2 N3 Pd'
_chemical_formula_weight         462.64
_chemical_name_systematic
;
Dichlorido[1-(1-naphthylmethyl)-3-(2-pyridyl)-1H-pyrazole-
κ²N²,N³]palladium(II)
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   9.330(6)
_cell_length_b                   12.139(8)
_cell_length_c                   15.918(11)
_cell_measurement_reflns_used    970
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3887
_cell_measurement_theta_min      3.3646
_cell_volume                     1803(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material
'SHELXTL (Bruker, 199 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10453
_diffrn_reflns_theta_full        26.48
_diffrn_reflns_theta_max         26.48
_diffrn_reflns_theta_min         2.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.332
_exptl_absorpt_correction_T_max  0.848
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.374
_refine_ls_abs_structure_details 'Flack (1983), 1580 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0241
_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)+(0.0227P)²+0.3859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0542
_reflns_number_gt                3340
_reflns_number_total             3702
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2262.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P21 21 21'
_cod_database_code               2216909
_cod_database_fobs_code          2216909
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'
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
Pd Pd1 0.83064(2) 0.490954(17) 0.051890(13) 0.03837(7) Uani d . 1
C C1 0.5698(4) 0.9043(3) 0.1086(3) 0.0546(9) Uani d . 1
H H1A 0.6381 0.9001 0.0662 0.065 Uiso calc R 1
C C2 0.5637(4) 0.9961(3) 0.1585(3) 0.0654(10) Uani d . 1
H H2A 0.6281 1.0534 0.1498 0.079 Uiso calc R 1
C C3 0.4620(4) 1.0044(4) 0.2221(2) 0.0704(12) Uani d . 1
H H3A 0.4589 1.0670 0.2557 0.084 Uiso calc R 1
C C4 0.3679(4) 0.9219(4) 0.2351(2) 0.0651(11) Uani d . 1
H H4A 0.2993 0.9290 0.2771 0.078 Uiso calc R 1
C C5 0.3714(3) 0.8245(3) 0.1859(2) 0.0511(9) Uani d . 1
C C6 0.2756(4) 0.7376(4) 0.1995(2) 0.0639(11) Uani d . 1
H H6A 0.2078 0.7433 0.2421 0.077 Uiso calc R 1
C C7 0.2800(4) 0.6453(3) 0.1516(3) 0.0613(10) Uani d . 1
H H7A 0.2168 0.5878 0.1622 0.074 Uiso calc R 1
C C8 0.3806(4) 0.6365(3) 0.0856(2) 0.0505(8) Uani d . 1
H H8A 0.3824 0.5730 0.0530 0.061 Uiso calc R 1
C C9 0.4752(3) 0.7192(2) 0.0689(2) 0.0408(7) Uani d . 1
C C10 0.4739(3) 0.8161(3) 0.1208(2) 0.0430(7) Uani d . 1
C C11 0.5803(3) 0.7164(2) -0.0027(2) 0.0444(8) Uani d . 1
H H11A 0.5576 0.7758 -0.0412 0.053 Uiso calc R 1
H H11B 0.6756 0.7301 0.0193 0.053 Uiso calc R 1
C C12 0.5032(4) 0.5886(3) -0.1173(2) 0.0534(8) Uani d . 1
H H12A 0.4323 0.6329 -0.1406 0.064 Uiso calc R 1
C C13 0.5448(3) 0.4872(3) -0.1465(2) 0.0512(8) Uani d . 1
H H13A 0.5090 0.4492 -0.1927 0.061 Uiso calc R 1
C C14 0.6522(3) 0.4540(2) -0.09185(19) 0.0397(7) Uani d . 1
C C15 0.7469(3) 0.3595(2) -0.0911(2) 0.0394(7) Uani d . 1
C C16 0.7465(4) 0.2785(3) -0.1518(2) 0.0479(8) Uani d . 1
H H16A 0.6799 0.2806 -0.1952 0.058 Uiso calc R 1
C C17 0.8446(4) 0.1953(3) -0.1477(3) 0.0612(10) Uani d . 1
H H17A 0.8459 0.1404 -0.1885 0.073 Uiso calc R 1
C C18 0.9416(5) 0.1935(3) -0.0826(3) 0.0675(13) Uani d . 1
H H18A 1.0096 0.1377 -0.0789 0.081 Uiso calc R 1
C C19 0.9366(4) 0.2753(3) -0.0231(3) 0.0619(11) Uani d . 1
H H19A 1.0022 0.2740 0.0209 0.074 Uiso calc R 1
N N1 0.5823(3) 0.6132(2) -0.04930(19) 0.0434(6) Uani d . 1
N N2 0.6739(3) 0.53078(17) -0.03249(14) 0.0378(5) Uani d . 1
N N3 0.8397(3) 0.35759(19) -0.02653(16) 0.0438(6) Uani d . 1
Cl Cl1 1.00048(11) 0.42155(9) 0.13879(7) 0.0708(3) Uani d . 1
Cl Cl2 0.81909(11) 0.64162(6) 0.13707(5) 0.0521(2) 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'
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
N2 Pd1 N3 79.38(10)
N2 Pd1 Cl1 171.74(7)
N3 Pd1 Cl1 92.83(9)
N2 Pd1 Cl2 99.63(7)
N3 Pd1 Cl2 178.86(7)
Cl1 Pd1 Cl2 88.18(5)
C2 C1 C10 120.8(4)
C2 C1 H1A 119.6
C10 C1 H1A 119.6
C1 C2 C3 120.6(4)
C1 C2 H2A 119.7
C3 C2 H2A 119.7
C4 C3 C2 120.2(4)
C4 C3 H3A 119.9
C2 C3 H3A 119.9
C3 C4 C5 121.3(4)
C3 C4 H4A 119.3
C5 C4 H4A 119.3
C6 C5 C10 119.4(3)
C6 C5 C4 121.9(4)
C10 C5 C4 118.6(4)
C7 C6 C5 121.1(4)
C7 C6 H6A 119.5
C5 C6 H6A 119.5
C6 C7 C8 120.1(4)
C6 C7 H7A 120.0
C8 C7 H7A 120.0
C9 C8 C7 121.3(3)
C9 C8 H8A 119.4
C7 C8 H8A 119.4
C8 C9 C10 119.0(3)
C8 C9 C11 123.6(3)
C10 C9 C11 117.3(3)
C1 C10 C5 118.5(3)
C1 C10 C9 122.5(3)
C5 C10 C9 119.1(3)
N1 C11 C9 114.4(3)
N1 C11 H11A 108.7
C9 C11 H11A 108.7
N1 C11 H11B 108.7
C9 C11 H11B 108.7
H11A C11 H11B 107.6
N1 C12 C13 108.5(3)
N1 C12 H12A 125.8
C13 C12 H12A 125.8
C12 C13 C14 104.6(3)
C12 C13 H13A 127.7
C14 C13 H13A 127.7
N2 C14 C13 110.4(3)
N2 C14 C15 116.8(3)
C13 C14 C15 132.6(3)
N3 C15 C16 121.7(3)
N3 C15 C14 114.4(3)
C16 C15 C14 123.9(3)
C17 C16 C15 119.5(4)
C17 C16 H16A 120.2
C15 C16 H16A 120.2
C16 C17 C18 119.2(3)
C16 C17 H17A 120.4
C18 C17 H17A 120.4
C19 C18 C17 119.1(4)
C19 C18 H18A 120.5
C17 C18 H18A 120.5
N3 C19 C18 122.0(4)
N3 C19 H19A 119.0
C18 C19 H19A 119.0
C12 N1 N2 110.2(3)
C12 N1 C11 126.5(3)
N2 N1 C11 123.2(3)
C14 N2 N1 106.3(2)
C14 N2 Pd1 113.99(19)
N1 N2 Pd1 139.7(2)
C15 N3 C19 118.4(3)
C15 N3 Pd1 115.2(2)
C19 N3 Pd1 126.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 N2 2.043(3)
Pd1 N3 2.046(3)
Pd1 Cl1 2.2658(14)
Pd1 Cl2 2.2792(14)
C1 C2 1.370(5)
C1 C10 1.408(5)
C1 H1A 0.930
C2 C3 1.390(6)
C2 H2A 0.930
C3 C4 1.347(6)
C3 H3A 0.930
C4 C5 1.418(5)
C4 H4A 0.930
C5 C6 1.399(5)
C5 C10 1.414(5)
C6 C7 1.356(6)
C6 H6A 0.930
C7 C8 1.413(5)
C7 H7A 0.930
C8 C9 1.363(5)
C8 H8A 0.930
C9 C10 1.438(4)
C9 C11 1.504(5)
C11 N1 1.456(4)
C11 H11A 0.970
C11 H11B 0.970
C12 N1 1.343(5)
C12 C13 1.372(5)
C12 H12A 0.930
C13 C14 1.387(4)
C13 H13A 0.930
C14 N2 1.342(4)
C14 C15 1.448(4)
C15 N3 1.343(4)
C15 C16 1.379(4)
C16 C17 1.365(5)
C16 H16A 0.930
C17 C18 1.377(6)
C17 H17A 0.930
C18 C19 1.373(5)
C18 H18A 0.930
C19 N3 1.348(4)
C19 H19A 0.930
N1 N2 1.343(3)
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
_geom_hbond_publ_flag
C17 H17A Cg1 2_664 0.93 2.89 3.602 134.4 yes
C18 H18A Cg2 4_555 0.93 3.05 3.803 139.4 yes
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
C10 C1 C2 C3 -0.3(5)
C1 C2 C3 C4 -0.2(6)
C2 C3 C4 C5 1.1(6)
C3 C4 C5 C6 179.1(3)
C3 C4 C5 C10 -1.6(5)
C10 C5 C6 C7 0.4(5)
C4 C5 C6 C7 179.6(4)
C5 C6 C7 C8 -1.2(6)
C6 C7 C8 C9 0.4(6)
C7 C8 C9 C10 1.3(5)
C7 C8 C9 C11 -177.3(3)
C2 C1 C10 C5 -0.2(5)
C2 C1 C10 C9 178.9(3)
C6 C5 C10 C1 -179.6(3)
C4 C5 C10 C1 1.1(5)
C6 C5 C10 C9 1.3(5)
C4 C5 C10 C9 -178.0(3)
C8 C9 C10 C1 178.8(3)
C11 C9 C10 C1 -2.5(5)
C8 C9 C10 C5 -2.1(5)
C11 C9 C10 C5 176.6(3)
C8 C9 C11 N1 -5.1(5)
C10 C9 C11 N1 176.2(3)
N1 C12 C13 C14 0.0(4)
C12 C13 C14 N2 0.3(4)
C12 C13 C14 C15 -174.8(3)
N2 C14 C15 N3 4.2(4)
C13 C14 C15 N3 179.2(3)
N2 C14 C15 C16 -174.3(3)
C13 C14 C15 C16 0.7(6)
N3 C15 C16 C17 -1.5(5)
C14 C15 C16 C17 176.9(3)
C15 C16 C17 C18 0.4(6)
C16 C17 C18 C19 0.3(6)
C17 C18 C19 N3 -0.1(7)
C13 C12 N1 N2 -0.4(4)
C13 C12 N1 C11 175.1(3)
C9 C11 N1 C12 90.9(4)
C9 C11 N1 N2 -94.1(3)
C13 C14 N2 N1 -0.6(3)
C15 C14 N2 N1 175.4(2)
C13 C14 N2 Pd1 -179.9(2)
C15 C14 N2 Pd1 -3.9(3)
C12 N1 N2 C14 0.6(3)
C11 N1 N2 C14 -175.1(3)
C12 N1 N2 Pd1 179.6(2)
C11 N1 N2 Pd1 4.0(5)
N3 Pd1 N2 C14 2.0(2)
Cl2 Pd1 N2 C14 -178.62(19)
N3 Pd1 N2 N1 -177.0(3)
Cl2 Pd1 N2 N1 2.4(3)
C16 C15 N3 C19 1.7(5)
C14 C15 N3 C19 -176.8(3)
C16 C15 N3 Pd1 176.1(2)
C14 C15 N3 Pd1 -2.4(3)
C18 C19 N3 C15 -0.9(6)
C18 C19 N3 Pd1 -174.7(3)
N2 Pd1 N3 C15 0.3(2)
Cl1 Pd1 N3 C15 177.6(2)
N2 Pd1 N3 C19 174.2(3)
Cl1 Pd1 N3 C19 -8.5(3)
