#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/63/2226305.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_2226305
loop_
_publ_author_name
'Anthony, Timothy A.'
'Arman, Hadi D.'
'Walmsley, Judith A.'
_publ_section_title
;
 Dichlorido(4,7-diaza-1-azoniacyclononane-κ²N⁴,N⁷)palladium(II)
 p-toluenesulfonate
;
_journal_coeditor_code           TK2666
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m638
_journal_page_last               m639
_journal_paper_doi               10.1107/S1600536810016533
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Pd Cl2 (C6 H16 N3)] (C7 H7 O3 S)'
_chemical_formula_moiety         'C6 H16 Cl2 N3 Pd +, C7 H7 O3 S -'
_chemical_formula_sum            'C13 H23 Cl2 N3 O3 Pd S'
_chemical_formula_weight         478.70
_chemical_name_systematic
;
Dichlorido(4,7-diaza-1-azoniacyclononane-
κ²N⁴,N⁷)palladium(II)
p-toluenesulfonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.149(3)
_cell_angle_beta                 92.301(3)
_cell_angle_gamma                103.084(4)
_cell_formula_units_Z            2
_cell_length_a                   6.6663(11)
_cell_length_b                   7.0023(11)
_cell_length_c                   19.646(3)
_cell_measurement_reflns_used    4441
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.2243
_cell_measurement_theta_min      2.9900
_cell_volume                     891.5(2)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector_area_resol_mean 14.286
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku AFC12 Kappa goniometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6224
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.473
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.977
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0288
_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)+(0.0070P)²+4.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0665
_reflns_number_gt                3941
_reflns_number_total             3998
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            tk2666.cif
_cod_data_source_block           I
_cod_database_code               2226305
_cod_database_fobs_code          2226305
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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 0.97009(3) 1.13904(3) 0.126918(10) 0.00972(6) Uani d . 1 . .
Cl Cl2 0.84514(10) 1.25666(9) 0.02940(3) 0.01338(13) Uani d . 1 . .
Cl Cl1 1.31092(10) 1.25684(10) 0.10367(3) 0.01477(13) Uani d . 1 . .
N N1 1.0477(4) 1.0307(3) 0.21612(12) 0.0107(4) Uani d . 1 . .
N N2 0.6749(3) 1.0232(3) 0.15540(12) 0.0119(4) Uani d . 1 . .
N N3 0.8065(4) 0.6217(4) 0.12108(13) 0.0131(5) Uani d . 1 . .
C C5 1.0277(4) 0.7097(4) 0.14512(15) 0.0135(5) Uani d . 1 . .
H H5A 1.0902 0.7978 0.1110 0.016 Uiso calc R 1 . .
H H5B 1.1000 0.6042 0.1465 0.016 Uiso calc R 1 . .
C C4 0.6940(4) 0.7353(4) 0.07501(14) 0.0133(5) Uani d . 1 . .
H H4A 0.6068 0.6428 0.0422 0.016 Uiso calc R 1 . .
H H4B 0.7954 0.8225 0.0497 0.016 Uiso calc R 1 . .
C C6 1.0657(4) 0.8215(4) 0.21375(14) 0.0125(5) Uani d . 1 . .
H H6A 0.9693 0.7511 0.2449 0.015 Uiso calc R 1 . .
H H6B 1.2032 0.8187 0.2311 0.015 Uiso calc R 1 . .
C C3 0.5617(4) 0.8563(4) 0.10909(15) 0.0139(5) Uani d . 1 . .
H H3B 0.4858 0.9082 0.0739 0.017 Uiso calc R 1 . .
H H3C 0.4616 0.7700 0.1352 0.017 Uiso calc R 1 . .
C C2 0.6799(4) 0.9703(4) 0.22882(14) 0.0150(5) Uani d . 1 . .
H H2B 0.6567 0.8290 0.2315 0.018 Uiso calc R 1 . .
H H2C 0.5715 1.0137 0.2522 0.018 Uiso calc R 1 . .
C C1 0.8864(4) 1.0674(4) 0.26239(14) 0.0143(5) Uani d . 1 . .
H H1B 0.8975 1.2073 0.2694 0.017 Uiso calc R 1 . .
H H1C 0.9036 1.0128 0.3063 0.017 Uiso calc R 1 . .
S S1 0.48600(10) 0.43932(10) 0.28213(3) 0.01295(14) Uani d . 1 . .
O O1 0.3964(3) 0.2362(3) 0.29720(10) 0.0153(4) Uani d . 1 . .
O O2 0.6622(3) 0.4531(3) 0.23865(10) 0.0162(4) Uani d . 1 . .
O O3 0.3348(4) 0.5425(3) 0.25768(12) 0.0240(5) Uani d . 1 . .
C C7 0.5938(5) 0.5596(4) 0.36084(15) 0.0168(6) Uani d . 1 . .
C C8 0.7933(5) 0.5552(5) 0.38198(17) 0.0244(7) Uani d . 1 . .
H H8A 0.8725 0.4937 0.3545 0.029 Uiso calc R 1 . .
C C9 0.8743(6) 0.6442(5) 0.44501(18) 0.0316(8) Uani d . 1 . .
H H9A 1.0087 0.6422 0.4590 0.038 Uiso calc R 1 . .
C C12 0.4771(6) 0.6539(5) 0.40103(18) 0.0286(7) Uani d . 1 . .
H H12A 0.3447 0.6602 0.3861 0.034 Uiso calc R 1 . .
C C11 0.5605(6) 0.7399(6) 0.4645(2) 0.0373(9) Uani d . 1 . .
H H11A 0.4811 0.8014 0.4919 0.045 Uiso calc R 1 . .
C C10 0.7584(6) 0.7355(5) 0.48716(17) 0.0329(9) Uani d . 1 . .
C C13 0.8478(8) 0.8282(7) 0.55589(19) 0.0492(13) Uani d . 1 . .
H H13A 0.7474 0.8842 0.5781 0.074 Uiso calc R 1 . .
H H13B 0.9686 0.9293 0.5496 0.074 Uiso calc R 1 . .
H H13C 0.8842 0.7299 0.5836 0.074 Uiso calc R 1 . .
H H1A 1.158(8) 1.102(8) 0.230(3) 0.059 Uiso d . 1 . .
H H2A 0.624(8) 1.114(8) 0.151(3) 0.059 Uiso d . 1 . .
H H3A 0.742(8) 0.592(8) 0.151(3) 0.059 Uiso d . 1 . .
H H3D 0.809(8) 0.516(8) 0.100(3) 0.059 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 0.0000 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'
S S 0.1246 0.1234 '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
N1 Pd1 N2 . . 82.71(9) y
N1 Pd1 Cl1 . . 92.14(7) ?
N2 Pd1 Cl1 . . 174.84(7) ?
N1 Pd1 Cl2 . . 173.69(7) ?
N2 Pd1 Cl2 . . 91.14(7) ?
Cl1 Pd1 Cl2 . . 94.02(3) y
C1 N1 C6 . . 112.8(2) ?
C1 N1 Pd1 . . 103.19(17) ?
C6 N1 Pd1 . . 116.87(17) ?
C1 N1 H1A . . 108(4) ?
C6 N1 H1A . . 109(4) ?
Pd1 N1 H1A . . 106(4) ?
C3 N2 C2 . . 112.6(2) ?
C3 N2 Pd1 . . 113.10(17) ?
C2 N2 Pd1 . . 109.76(17) ?
C3 N2 H2A . . 109(4) ?
C2 N2 H2A . . 110(4) ?
Pd1 N2 H2A . . 101(4) ?
C4 N3 C5 . . 119.6(2) ?
C4 N3 H3A . . 108(4) ?
C5 N3 H3A . . 110(4) ?
C4 N3 H3D . . 107(4) ?
C5 N3 H3D . . 105(4) ?
H3A N3 H3D . . 105(5) ?
N3 C5 C6 . . 117.7(2) ?
N3 C5 H5A . . 107.9 ?
C6 C5 H5A . . 107.9 ?
N3 C5 H5B . . 107.9 ?
C6 C5 H5B . . 107.9 ?
H5A C5 H5B . . 107.2 ?
N3 C4 C3 . . 116.7(2) ?
N3 C4 H4A . . 108.1 ?
C3 C4 H4A . . 108.1 ?
N3 C4 H4B . . 108.1 ?
C3 C4 H4B . . 108.1 ?
H4A C4 H4B . . 107.3 ?
N1 C6 C5 . . 117.5(2) ?
N1 C6 H6A . . 107.9 ?
C5 C6 H6A . . 107.9 ?
N1 C6 H6B . . 107.9 ?
C5 C6 H6B . . 107.9 ?
H6A C6 H6B . . 107.2 ?
N2 C3 C4 . . 115.6(2) ?
N2 C3 H3B . . 108.4 ?
C4 C3 H3B . . 108.4 ?
N2 C3 H3C . . 108.4 ?
C4 C3 H3C . . 108.4 ?
H3B C3 H3C . . 107.4 ?
N2 C2 C1 . . 109.3(2) ?
N2 C2 H2B . . 109.8 ?
C1 C2 H2B . . 109.8 ?
N2 C2 H2C . . 109.8 ?
C1 C2 H2C . . 109.8 ?
H2B C2 H2C . . 108.3 ?
N1 C1 C2 . . 107.4(2) ?
N1 C1 H1B . . 110.2 ?
C2 C1 H1B . . 110.2 ?
N1 C1 H1C . . 110.2 ?
C2 C1 H1C . . 110.2 ?
H1B C1 H1C . . 108.5 ?
O3 S1 O1 . . 113.12(13) ?
O3 S1 O2 . . 113.98(13) ?
O1 S1 O2 . . 111.41(12) ?
O3 S1 C7 . . 106.63(14) ?
O1 S1 C7 . . 106.18(13) ?
O2 S1 C7 . . 104.72(13) ?
C12 C7 C8 . . 120.5(3) ?
C12 C7 S1 . . 119.9(3) ?
C8 C7 S1 . . 119.7(2) ?
C7 C8 C9 . . 119.3(3) ?
C7 C8 H8A . . 120.3 ?
C9 C8 H8A . . 120.3 ?
C10 C9 C8 . . 121.4(4) ?
C10 C9 H9A . . 119.3 ?
C8 C9 H9A . . 119.3 ?
C7 C12 C11 . . 119.3(4) ?
C7 C12 H12A . . 120.4 ?
C11 C12 H12A . . 120.4 ?
C10 C11 C12 . . 121.4(3) ?
C10 C11 H11A . . 119.3 ?
C12 C11 H11A . . 119.3 ?
C11 C10 C9 . . 118.1(3) ?
C11 C10 C13 . . 121.3(4) ?
C9 C10 C13 . . 120.6(4) ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 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
Pd1 N1 . 2.030(2) y
Pd1 N2 . 2.060(2) y
Pd1 Cl1 . 2.3053(8) y
Pd1 Cl2 . 2.3115(7) y
N1 C1 . 1.495(3) ?
N1 C6 . 1.495(3) ?
N1 H1A . 0.82(5) ?
N2 C3 . 1.493(3) ?
N2 C2 . 1.504(4) ?
N2 H2A . 0.79(5) ?
N3 C4 . 1.511(4) ?
N3 C5 . 1.512(4) ?
N3 H3A . 0.76(6) ?
N3 H3D . 0.83(6) ?
C5 C6 . 1.516(4) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C4 C3 . 1.512(4) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C3 H3B . 0.9700 ?
C3 H3C . 0.9700 ?
C2 C1 . 1.504(4) ?
C2 H2B . 0.9700 ?
C2 H2C . 0.9700 ?
C1 H1B . 0.9700 ?
C1 H1C . 0.9700 ?
S1 O3 . 1.444(2) ?
S1 O1 . 1.459(2) ?
S1 O2 . 1.468(2) ?
S1 C7 . 1.777(3) ?
C7 C12 . 1.381(4) ?
C7 C8 . 1.385(5) ?
C8 C9 . 1.396(5) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.388(6) ?
C9 H9A . 0.9300 ?
C12 C11 . 1.400(5) ?
C12 H12A . 0.9300 ?
C11 C10 . 1.383(6) ?
C11 H11A . 0.9300 ?
C10 C13 . 1.515(5) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
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
N1 H1a O1 1_665 0.82(6) 2.05(6) 2.833(3) 159(6)
N2 H2a Cl1 1_455 0.79(5) 2.66(6) 3.365(2) 149(5)
N3 H3a O2 1_555 0.75(6) 2.04(6) 2.743(3) 156(6)
N3 H3d Cl2 1_545 0.84(5) 2.31(6) 3.136(3) 171(5)
