#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/08/2210802.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_2210802
loop_
_publ_author_name
'Okabe, Nobuo'
'Mizubayashi, Yu'
'Odoko, Mamiko'
_publ_section_title
(Cyclobutane-1,1-dicarboxylato-κ²O,O')(di-2-pyridylamine-κ²N,N')palladium(II)
_journal_coeditor_code           TK2079
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2747
_journal_page_last               m2749
_journal_paper_doi               10.1107/S1600536806038773
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Pd (C6 H6 O2) (C10 H9 N3)]'
_chemical_formula_moiety         'C16 H15 N3 O4 Pd'
_chemical_formula_sum            'C16 H15 N3 O4 Pd'
_chemical_formula_weight         419.73
_chemical_name_systematic
;
(Cyclobutane-1,1-dicarboxylato-κ²O,O')(di-2-pyridylamine-
κ²N,N')palladium(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                67.92(3)
_cell_angle_beta                 67.30(2)
_cell_angle_gamma                71.21(3)
_cell_formula_units_Z            2
_cell_length_a                   9.115(6)
_cell_length_b                   9.698(8)
_cell_length_c                   10.227(6)
_cell_measurement_reflns_used    7195
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     756.1(9)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction
;
CrystalStructure (Rigaku/MSC, 2005) and
CRYSTALS (Betteridge et al.,  2003)
;
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9859
_diffrn_measured_fraction_theta_max 0.9859
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.013
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7482
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.254
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.49
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3425
_refine_ls_R_factor_gt           0.020
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0453P)²+0.0721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.074
_reflns_number_gt                3244
_reflns_number_total             3425
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            tk2079.cif
_cod_data_source_block           I
_cod_database_code               2210802
_cod_database_fobs_code          2210802
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-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
Pd Pd1 0.169224(18) 0.375556(16) 0.393389(16) 0.02605(8) Uani d . 1 . .
O O1 0.2241(2) 0.4938(2) 0.48770(19) 0.0367(4) Uani d . 1 . .
O O2 0.2902(3) 0.7033(2) 0.4643(2) 0.0453(4) Uani d . 1 . .
O O3 0.1963(3) 0.7820(2) 0.0782(2) 0.0483(5) Uani d . 1 B .
O O4 0.1313(2) 0.56613(19) 0.2316(2) 0.0379(4) Uani d . 1 B .
N N1 0.1015(2) 0.2661(2) 0.3010(2) 0.0282(4) Uani d . 1 . .
N N2 0.2479(2) 0.0244(2) 0.4058(2) 0.0327(4) Uani d . 1 . .
H H5 0.3042 -0.0591 0.3854 0.039 Uiso calc R 1 . .
N N3 0.2170(2) 0.1812(2) 0.5500(2) 0.0276(4) Uani d . 1 . .
C C1 0.0044(3) 0.3489(3) 0.2129(3) 0.0357(5) Uani d . 1 . .
H H1 -0.0392 0.4508 0.2090 0.043 Uiso calc R 1 . .
C C2 -0.0319(3) 0.2901(3) 0.1304(3) 0.0385(5) Uani d . 1 . .
H H2 -0.0964 0.3513 0.0696 0.046 Uiso calc R 1 . .
C C3 0.0291(3) 0.1366(3) 0.1384(3) 0.0377(5) Uani d . 1 . .
H H3 0.0077 0.0940 0.0817 0.045 Uiso calc R 1 . .
C C4 0.1216(3) 0.0495(3) 0.2317(3) 0.0362(5) Uani d . 1 . .
H H4 0.1619 -0.0536 0.2401 0.043 Uiso calc R 1 . .
C C5 0.1547(3) 0.1169(2) 0.3139(2) 0.0282(4) Uani d . 1 . .
C C6 0.2648(3) 0.0447(2) 0.5250(2) 0.0276(4) Uani d . 1 . .
C C7 0.3362(3) -0.0838(3) 0.6194(3) 0.0343(5) Uani d . 1 . .
H H6 0.3755 -0.1761 0.5972 0.041 Uiso calc R 1 . .
C C8 0.3478(3) -0.0724(3) 0.7440(3) 0.0384(5) Uani d . 1 . .
H H7 0.3959 -0.1566 0.8070 0.046 Uiso calc R 1 . .
C C9 0.2872(3) 0.0661(3) 0.7759(3) 0.0381(5) Uani d . 1 . .
H H8 0.2891 0.0749 0.8627 0.046 Uiso calc R 1 . .
C C10 0.2247(3) 0.1893(3) 0.6773(3) 0.0339(5) Uani d . 1 . .
H H9 0.1860 0.2825 0.6979 0.041 Uiso calc R 1 . .
C C11 0.2859(3) 0.6127(2) 0.4091(3) 0.0297(4) Uani d . 1 . .
C C12 0.3576(3) 0.6365(2) 0.2417(3) 0.0298(4) Uani d . 1 B .
C C13 0.5033(3) 0.5061(3) 0.1996(3) 0.0445(6) Uani d . 1 . .
H H13A 0.5175 0.4184 0.2833 0.053 Uiso calc R 1 A 1
H H13B 0.5025 0.4758 0.1197 0.053 Uiso calc R 1 A 1
C C14A 0.6161(12) 0.6093(14) 0.1521(12) 0.067(3) Uani d P 0.50 B 1
H H14A 0.6914 0.6150 0.0534 0.081 Uiso calc PR 0.50 B 1
H H14B 0.6737 0.5873 0.2224 0.081 Uiso calc PR 0.50 B 1
C C14B 0.6014(12) 0.6315(12) 0.0897(9) 0.0517(19) Uani d P 0.50 B 2
H H14C 0.7067 0.6152 0.1019 0.062 Uiso calc PR 0.50 B 2
H H14D 0.6115 0.6497 -0.0131 0.062 Uiso calc PR 0.50 B 2
C C15 0.4738(3) 0.7484(3) 0.1584(3) 0.0417(6) Uani d . 1 . .
H H15A 0.4624 0.8122 0.0622 0.050 Uiso calc R 1 B 1
H H15B 0.4723 0.8084 0.2165 0.050 Uiso calc R 1 B 1
C C16 0.2197(3) 0.6673(2) 0.1765(2) 0.0307(4) 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 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Pd Pd -0.999 1.007
;
International Tables for Crystallography
(1992, 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
O1 Pd1 O4 89.60(9) yes
O1 Pd1 N1 176.60(7) yes
O1 Pd1 N3 90.90(9) yes
O4 Pd1 N1 88.71(10) yes
O4 Pd1 N3 177.47(7) yes
N1 Pd1 N3 90.92(10) yes
C11 O1 Pd1 121.20(15) ?
C16 O4 Pd1 122.66(15) ?
C5 N1 C1 118.0(2) ?
C5 N1 Pd1 123.49(16) ?
C1 N1 Pd1 118.39(16) ?
C6 N2 C5 130.2(2) ?
C6 N2 H5 114.9 ?
C5 N2 H5 114.9 ?
C6 N3 C10 118.3(2) ?
C6 N3 Pd1 122.14(16) ?
C10 N3 Pd1 118.83(16) ?
C2 C1 N1 123.2(2) ?
C2 C1 H1 118.4 ?
N1 C1 H1 118.4 ?
C1 C2 C3 118.9(2) ?
C1 C2 H2 120.5 ?
C3 C2 H2 120.5 ?
C4 C3 C2 118.7(2) ?
C4 C3 H3 120.6 ?
C2 C3 H3 120.6 ?
C3 C4 C5 119.6(2) ?
C3 C4 H4 120.2 ?
C5 C4 H4 120.2 ?
N1 C5 N2 121.37(19) ?
N1 C5 C4 121.4(2) ?
N2 C5 C4 117.2(2) ?
N3 C6 N2 121.9(2) ?
N3 C6 C7 121.1(2) ?
N2 C6 C7 117.0(2) ?
C8 C7 C6 119.6(2) ?
C8 C7 H6 120.2 ?
C6 C7 H6 120.2 ?
C7 C8 C9 119.3(2) ?
C7 C8 H7 120.3 ?
C9 C8 H7 120.3 ?
C10 C9 C8 118.8(2) ?
C10 C9 H8 120.6 ?
C8 C9 H8 120.6 ?
N3 C10 C9 122.6(2) ?
N3 C10 H9 118.7 ?
C9 C10 H9 118.7 ?
O2 C11 O1 122.3(2) ?
O2 C11 C12 120.4(2) ?
O1 C11 C12 117.35(19) ?
C11 C12 C16 109.09(19) ?
C11 C12 C15 115.65(19) ?
C16 C12 C15 115.0(2) ?
C11 C12 C13 113.05(19) ?
C16 C12 C13 114.18(19) ?
C15 C12 C13 88.8(2) ?
C14A C13 C12 89.2(5) ?
C12 C13 C14B 87.7(4) ?
C14A C13 H13A 113.8 ?
C12 C13 H13A 113.8 ?
C14B C13 H13A 135.8 ?
C14A C13 H13B 113.8 ?
C12 C13 H13B 113.8 ?
C14B C13 H13B 92.3 ?
H13A C13 H13B 111.0 ?
C13 C14A C15 91.5(6) ?
C13 C14A H14A 113.4 ?
C15 C14A H14A 113.4 ?
C13 C14A H14B 113.4 ?
C15 C14A H14B 113.4 ?
H14A C14A H14B 110.7 ?
C15 C14B C13 90.2(5) ?
C15 C14B H14C 113.6 ?
C13 C14B H14C 113.6 ?
C15 C14B H14D 113.6 ?
C13 C14B H14D 113.6 ?
H14C C14B H14D 110.9 ?
C14B C15 C12 90.7(4) ?
C14A C15 C12 87.9(5) ?
C14B C15 H15A 90.8 ?
C14A C15 H15A 114.0 ?
C12 C15 H15A 114.0 ?
C14B C15 H15B 133.7 ?
C14A C15 H15B 114.0 ?
C12 C15 H15B 114.0 ?
H15A C15 H15B 111.2 ?
O3 C16 O4 122.3(2) ?
O3 C16 C12 120.6(2) ?
O4 C16 C12 117.10(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Pd1 O1 2.0169(19) yes
Pd1 O4 2.001(2) yes
Pd1 N1 2.007(2) yes
Pd1 N3 2.012(2) yes
O1 C11 1.291(3) ?
O2 C11 1.227(3) ?
O3 C16 1.211(3) ?
O4 C16 1.293(3) ?
N1 C5 1.341(3) ?
N1 C1 1.362(3) ?
N2 C6 1.377(3) ?
N2 C5 1.378(3) ?
N2 H5 0.8600 ?
N3 C6 1.343(3) ?
N3 C10 1.363(3) ?
C1 C2 1.358(4) ?
C1 H1 0.9300 ?
C2 C3 1.394(4) ?
C2 H2 0.9300 ?
C3 C4 1.375(3) ?
C3 H3 0.9300 ?
C4 C5 1.401(3) ?
C4 H4 0.9300 ?
C6 C7 1.402(3) ?
C7 C8 1.366(3) ?
C7 H6 0.9300 ?
C8 C9 1.389(4) ?
C8 H7 0.9300 ?
C9 C10 1.367(4) ?
C9 H8 0.9300 ?
C10 H9 0.9300 ?
C11 C12 1.532(3) ?
C12 C16 1.539(3) ?
C12 C15 1.541(3) ?
C12 C13 1.560(3) ?
C13 C14A 1.486(13) ?
C13 C14B 1.562(11) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14A C15 1.542(11) ?
C14A H14A 0.9700 ?
C14A H14B 0.9700 ?
C14B C15 1.500(11) ?
C14B H14C 0.9700 ?
C14B H14D 0.9700 ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
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
N2 H5 O2 1_545 0.86 2.17 2.865(4) 138 no
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
O4 Pd1 O1 C11 -28.75(19)
N3 Pd1 O1 C11 148.76(19)
N1 Pd1 O4 C16 -145.1(2)
O1 Pd1 O4 C16 37.8(2)
O4 Pd1 N1 C5 152.17(19)
N3 Pd1 N1 C5 -25.33(19)
O4 Pd1 N1 C1 -23.57(19)
N3 Pd1 N1 C1 158.94(19)
N1 Pd1 N3 C6 29.41(18)
O1 Pd1 N3 C6 -153.47(18)
N1 Pd1 N3 C10 -160.57(18)
O1 Pd1 N3 C10 16.56(18)
C5 N1 C1 C2 -4.5(4)
Pd1 N1 C1 C2 171.5(2)
N1 C1 C2 C3 1.7(4)
C1 C2 C3 C4 1.2(4)
C2 C3 C4 C5 -1.2(4)
C1 N1 C5 N2 -177.3(2)
Pd1 N1 C5 N2 6.9(3)
C1 N1 C5 C4 4.4(3)
Pd1 N1 C5 C4 -171.35(18)
C6 N2 C5 N1 20.9(4)
C6 N2 C5 C4 -160.8(2)
C3 C4 C5 N1 -1.7(4)
C3 C4 C5 N2 180.0(2)
C10 N3 C6 N2 174.3(2)
Pd1 N3 C6 N2 -15.6(3)
C10 N3 C6 C7 -6.4(3)
Pd1 N3 C6 C7 163.71(17)
C5 N2 C6 N3 -16.0(4)
C5 N2 C6 C7 164.7(2)
N3 C6 C7 C8 4.3(4)
N2 C6 C7 C8 -176.3(2)
C6 C7 C8 C9 0.6(4)
C7 C8 C9 C10 -3.2(4)
C6 N3 C10 C9 3.7(3)
Pd1 N3 C10 C9 -166.75(19)
C8 C9 C10 N3 1.1(4)
Pd1 O1 C11 O2 165.05(19)
Pd1 O1 C11 C12 -15.9(3)
O2 C11 C12 C16 -114.7(2)
O1 C11 C12 C16 66.2(3)
O2 C11 C12 C15 16.8(3)
O1 C11 C12 C15 -162.3(2)
O2 C11 C12 C13 117.1(3)
O1 C11 C12 C13 -62.0(3)
C11 C12 C13 C14A -105.1(5)
C16 C12 C13 C14A 129.4(5)
C15 C12 C13 C14A 12.4(5)
C11 C12 C13 C14B -129.3(4)
C16 C12 C13 C14B 105.2(4)
C15 C12 C13 C14B -11.9(4)
C12 C13 C14A C15 -12.4(5)
C12 C13 C14B C15 12.2(4)
C13 C14B C15 C12 -12.3(4)
C13 C14A C15 C12 12.5(5)
C11 C12 C15 C14B 127.4(4)
C16 C12 C15 C14B -103.9(4)
C13 C12 C15 C14B 12.3(4)
C11 C12 C15 C14A 103.2(5)
C16 C12 C15 C14A -128.2(5)
C13 C12 C15 C14A -11.9(5)
Pd1 O4 C16 O3 179.70(19)
Pd1 O4 C16 C12 -0.5(3)
C11 C12 C16 O3 123.5(2)
C15 C12 C16 O3 -8.4(3)
C13 C12 C16 O3 -109.0(3)
C11 C12 C16 O4 -56.3(3)
C15 C12 C16 O4 171.8(2)
C13 C12 C16 O4 71.2(3)
