#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227027.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_2227027
loop_
_publ_author_name
'Lin, Meng-Ling'
'Tsai, Chen-Yen'
'Li, Chen-Yu'
'Huang, Bor-Hunn'
'Ko, Bao-Tsan'
_publ_section_title
;
 Bis{1-[(E)-(2-methylphenyl)diazenyl]-2-naphtholato}palladium(II)
;
_journal_coeditor_code           NK2047
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1022
_journal_paper_doi               10.1107/S1600536810028916
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Pd (C17 H13 N2 O)2]'
_chemical_formula_moiety         'C34 H26 N4 O2 Pd'
_chemical_formula_sum            'C34 H26 N4 O2 Pd'
_chemical_formula_weight         628.99
_chemical_name_systematic
;
Bis{1-[(E)-(2-methylphenyl)diazenyl]-2-naphtholato}palladium(II)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 94.151(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.9997(7)
_cell_length_b                   4.8374(2)
_cell_length_c                   24.7294(7)
_cell_measurement_reflns_used    7356
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.34
_cell_volume                     2744.14(16)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12830
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  0.9002
_exptl_absorpt_correction_T_min  0.7828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.388
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0308P)²+8.4214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0912
_reflns_number_gt                2463
_reflns_number_total             3412
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            nk2047.cif
_cod_data_source_block           I
_cod_original_cell_volume        2744.15(16)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2227027
_cod_database_fobs_code          2227027
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd 0.2500 0.7500 1.0000 0.03581(10) Uani d S 1 . .
O O 0.25231(10) 0.8334(5) 0.92226(8) 0.0515(6) Uani d . 1 . .
N N1 0.34684(10) 0.4378(5) 0.95474(9) 0.0395(5) Uani d . 1 . .
N N2 0.32263(10) 0.5212(5) 0.99676(9) 0.0383(5) Uani d . 1 . .
C C1 0.28284(12) 0.7041(7) 0.88889(11) 0.0412(7) Uani d . 1 . .
C C2 0.32620(11) 0.5049(7) 0.90302(10) 0.0383(6) Uani d . 1 . .
C C3 0.35764(12) 0.3717(7) 0.86127(11) 0.0418(7) Uani d . 1 . .
C C4 0.40016(14) 0.1696(8) 0.87324(13) 0.0528(8) Uani d . 1 . .
H H4A 0.4087 0.1152 0.9090 0.063 Uiso calc R 1 . .
C C5 0.42950(15) 0.0503(9) 0.83250(15) 0.0667(11) Uani d . 1 . .
H H5A 0.4575 -0.0845 0.8410 0.080 Uiso calc R 1 . .
C C6 0.41752(17) 0.1303(11) 0.77874(15) 0.0745(12) Uani d . 1 . .
H H6A 0.4381 0.0519 0.7516 0.089 Uiso calc R 1 . .
C C7 0.37581(16) 0.3227(9) 0.76598(13) 0.0625(10) Uani d . 1 . .
H H7A 0.3675 0.3721 0.7299 0.075 Uiso calc R 1 . .
C C8 0.34474(13) 0.4492(8) 0.80650(12) 0.0485(8) Uani d . 1 . .
C C9 0.30133(14) 0.6511(8) 0.79407(12) 0.0539(8) Uani d . 1 . .
H H9A 0.2930 0.7018 0.7581 0.065 Uiso calc R 1 . .
C C10 0.27170(14) 0.7722(7) 0.83272(12) 0.0492(8) Uani d . 1 . .
H H10A 0.2433 0.9031 0.8227 0.059 Uiso calc R 1 . .
C C11 0.35700(12) 0.4466(6) 1.04613(11) 0.0388(6) Uani d . 1 . .
C C12 0.33396(14) 0.2599(7) 1.08096(12) 0.0457(7) Uani d . 1 . .
H H12A 0.2972 0.1845 1.0727 0.055 Uiso calc R 1 . .
C C13 0.36591(17) 0.1857(8) 1.12820(14) 0.0611(10) Uani d . 1 . .
H H13A 0.3510 0.0577 1.1516 0.073 Uiso calc R 1 . .
C C14 0.41908(16) 0.3001(9) 1.14040(14) 0.0651(11) Uani d . 1 . .
H H14A 0.4403 0.2519 1.1725 0.078 Uiso calc R 1 . .
C C15 0.44195(14) 0.4868(9) 1.10574(13) 0.0596(9) Uani d . 1 . .
H H15A 0.4786 0.5620 1.1148 0.071 Uiso calc R 1 . .
C C16 0.41154(12) 0.5661(7) 1.05728(12) 0.0440(7) Uani d . 1 . .
C C17 0.43715(16) 0.7699(8) 1.02047(16) 0.0627(10) Uani d . 1 . .
H H17A 0.4105 0.8002 0.9893 0.094 Uiso calc R 1 . .
H H17B 0.4733 0.6992 1.0090 0.094 Uiso calc R 1 . .
H H17C 0.4441 0.9413 1.0394 0.094 Uiso calc R 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
O Pd O . 7_567 180.00(13) ?
O Pd N2 . . 89.58(9) ?
O Pd N2 7_567 . 90.43(9) ?
O Pd N2 . 7_567 90.43(9) ?
O Pd N2 7_567 7_567 89.57(9) ?
N2 Pd N2 . 7_567 180.00(14) ?
C1 O Pd . . 125.6(2) ?
N2 N1 C2 . . 122.8(2) ?
N1 N2 C11 . . 111.3(2) ?
N1 N2 Pd . . 128.15(18) ?
C11 N2 Pd . . 120.46(17) ?
O C1 C2 . . 125.6(3) ?
O C1 C10 . . 116.3(3) ?
C2 C1 C10 . . 118.0(3) ?
N1 C2 C1 . . 125.7(3) ?
N1 C2 C3 . . 113.7(3) ?
C1 C2 C3 . . 120.4(3) ?
C4 C3 C8 . . 118.8(3) ?
C4 C3 C2 . . 122.4(3) ?
C8 C3 C2 . . 118.8(3) ?
C5 C4 C3 . . 120.6(3) ?
C5 C4 H4A . . 119.7 ?
C3 C4 H4A . . 119.7 ?
C4 C5 C6 . . 120.5(4) ?
C4 C5 H5A . . 119.7 ?
C6 C5 H5A . . 119.7 ?
C7 C6 C5 . . 120.0(3) ?
C7 C6 H6A . . 120.0 ?
C5 C6 H6A . . 120.0 ?
C6 C7 C8 . . 121.2(3) ?
C6 C7 H7A . . 119.4 ?
C8 C7 H7A . . 119.4 ?
C7 C8 C9 . . 122.0(3) ?
C7 C8 C3 . . 118.9(3) ?
C9 C8 C3 . . 119.1(3) ?
C10 C9 C8 . . 122.1(3) ?
C10 C9 H9A . . 119.0 ?
C8 C9 H9A . . 119.0 ?
C9 C10 C1 . . 121.6(3) ?
C9 C10 H10A . . 119.2 ?
C1 C10 H10A . . 119.2 ?
C12 C11 C16 . . 122.0(3) ?
C12 C11 N2 . . 118.5(3) ?
C16 C11 N2 . . 119.5(3) ?
C11 C12 C13 . . 119.5(3) ?
C11 C12 H12A . . 120.2 ?
C13 C12 H12A . . 120.2 ?
C14 C13 C12 . . 119.9(3) ?
C14 C13 H13A . . 120.1 ?
C12 C13 H13A . . 120.1 ?
C13 C14 C15 . . 120.6(3) ?
C13 C14 H14A . . 119.7 ?
C15 C14 H14A . . 119.7 ?
C14 C15 C16 . . 121.6(3) ?
C14 C15 H15A . . 119.2 ?
C16 C15 H15A . . 119.2 ?
C11 C16 C15 . . 116.4(3) ?
C11 C16 C17 . . 123.0(3) ?
C15 C16 C17 . . 120.6(3) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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
Pd O . 1.9687(19) ?
Pd O 7_567 1.9688(19) ?
Pd N2 . 2.010(2) ?
Pd N2 7_567 2.010(2) ?
O C1 . 1.284(4) ?
N1 N2 . 1.279(3) ?
N1 C2 . 1.371(3) ?
N2 C11 . 1.451(3) ?
C1 C2 . 1.412(4) ?
C1 C10 . 1.433(4) ?
C2 C3 . 1.453(4) ?
C3 C4 . 1.399(5) ?
C3 C8 . 1.416(4) ?
C4 C5 . 1.379(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.393(5) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.357(6) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.412(4) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.414(5) ?
C9 C10 . 1.347(5) ?
C9 H9A . 0.9300 ?
C10 H10A . 0.9300 ?
C11 C12 . 1.380(4) ?
C11 C16 . 1.390(4) ?
C12 C13 . 1.382(4) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.356(5) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.375(5) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.397(4) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.492(5) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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
N2 Pd O C1 . . . . 15.3(3) ?
N2 Pd O C1 7_567 . . . -164.7(3) ?
C2 N1 N2 C11 . . . . -173.5(3) ?
C2 N1 N2 Pd . . . . 2.2(4) ?
O Pd N2 N1 . . . . -12.3(3) ?
O Pd N2 N1 7_567 . . . 167.7(3) ?
O Pd N2 C11 . . . . 163.1(2) ?
O Pd N2 C11 7_567 . . . -16.9(2) ?
Pd O C1 C2 . . . . -9.3(5) ?
Pd O C1 C10 . . . . 171.2(2) ?
N2 N1 C2 C1 . . . . 10.7(5) ?
N2 N1 C2 C3 . . . . -175.7(3) ?
O C1 C2 N1 . . . . -7.1(5) ?
C10 C1 C2 N1 . . . . 172.4(3) ?
O C1 C2 C3 . . . . 179.7(3) ?
C10 C1 C2 C3 . . . . -0.9(4) ?
N1 C2 C3 C4 . . . . 7.2(4) ?
C1 C2 C3 C4 . . . . -178.8(3) ?
N1 C2 C3 C8 . . . . -172.9(3) ?
C1 C2 C3 C8 . . . . 1.2(4) ?
C8 C3 C4 C5 . . . . 0.8(5) ?
C2 C3 C4 C5 . . . . -179.3(3) ?
C3 C4 C5 C6 . . . . 0.4(6) ?
C4 C5 C6 C7 . . . . -1.4(7) ?
C5 C6 C7 C8 . . . . 1.3(7) ?
C6 C7 C8 C9 . . . . 179.7(4) ?
C6 C7 C8 C3 . . . . -0.1(6) ?
C4 C3 C8 C7 . . . . -0.9(5) ?
C2 C3 C8 C7 . . . . 179.2(3) ?
C4 C3 C8 C9 . . . . 179.3(3) ?
C2 C3 C8 C9 . . . . -0.7(5) ?
C7 C8 C9 C10 . . . . -179.9(3) ?
C3 C8 C9 C10 . . . . -0.1(5) ?
C8 C9 C10 C1 . . . . 0.4(5) ?
O C1 C10 C9 . . . . 179.6(3) ?
C2 C1 C10 C9 . . . . 0.1(5) ?
N1 N2 C11 C12 . . . . -114.3(3) ?
Pd N2 C11 C12 . . . . 69.6(3) ?
N1 N2 C11 C16 . . . . 66.3(4) ?
Pd N2 C11 C16 . . . . -109.8(3) ?
C16 C11 C12 C13 . . . . -0.7(5) ?
N2 C11 C12 C13 . . . . 180.0(3) ?
C11 C12 C13 C14 . . . . 1.1(5) ?
C12 C13 C14 C15 . . . . -0.9(6) ?
C13 C14 C15 C16 . . . . 0.3(6) ?
C12 C11 C16 C15 . . . . 0.1(5) ?
N2 C11 C16 C15 . . . . 179.4(3) ?
C12 C11 C16 C17 . . . . -179.5(3) ?
N2 C11 C16 C17 . . . . -0.2(5) ?
C14 C15 C16 C11 . . . . 0.1(5) ?
C14 C15 C16 C17 . . . . 179.7(4) ?
