data_global

_publ_requested_journal          'Acta Crystallographica Section E'

_publ_contact_author_name        'Dr Pengfei Shi'
_publ_contact_author_address     
; State Key Laboratory of Coordination Chemistry
  Nanjing University 
  Nanjing 210093
  People's Republic of China
;
_publ_contact_author_email       shipengfei@lianluo.com
_publ_contact_author_phone       (+86)-25-83594549
_publ_contact_author_fax         (+86)-25-83314502
loop_
_publ_author_name
_publ_author_address
'Shi, Pengfei'
; State Key Laboratory of Coordination Chemistry
  Nanjing University
  Nanjing 210093
  People's Republic of China
;

#==========================================================================

_audit_creation_method           SHELXL-97
_audit_creation_date             '25 March 2006'

#==========================================================================

# PROCESSING SUMMARY  (IUCr Office Use Only)

_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          
; ?
;
_journal_techeditor_code         ?
_journal_techeditor_notes        
; ?
;
_journal_coden_ASTM              ?
_journal_name_full               ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

#==========================================================================

# SUBMISSION DETAILS

_publ_contact_letter             
;
Date of submission:  2006-3-25

Please consider this CIF submission for publication in Acta Cryst. Section 
E.  I certify that all authors have seen and approved of this submission, 
that all have made significant scientific contributions to the work 
reported, and that all share responsibility and accountability for the
results.

The CIF has passed the Chester CHECKCIF routines and all possible Alerts
have been responded to.  The CIF also gives a satisfactory PRINTCIF file.
When you reply by e-mail with your reference number I will return the
Copyright Transfer Form.

Best wishes,
Pengfei Shi
;
_publ_requested_category         EI
_publ_requested_coeditor_name    ?

#==========================================================================
# TITLE AND AUTHOR LIST

_publ_section_title              
;
Gold(III) complex of DPA(2,2-dipyridinylamine)
;

_publ_section_title_footnote     
.
loop_
_publ_author_footnote
.
.
#==========================================================================
# TEXT

_publ_section_abstract           
;
Gold(III) complex of DPA(2,2-dipyridinylamine) has been synthesized and
characterized by ESI-MS,^1^H NMR spectroscopy and elemental analyses. Its
structure was determinied by X-ray crystallography, in which DPA coordinates
to the gold(III) center in a bidentate mode. The unbound cl anion forms a very
short intermolecular Au-cl contact (3.037 angstrom), which bridge the cations
into two-dimensional sheet together with hydrogen bonds.The title complex is
more cytotoxic than cisplatin against A-549 and HCT-116 tumor cell lines.
;

_publ_section_comment            
;
Gold(III) is isoelectronic and isostructural to Pt(II), therefore its complexes
have long been evaluated as potential anticancer agents. (Shaw <i>et al.</i>,
1999)However,because of the high reductive potential gold(III) complexes are
not very stable under physiological conditions. (Messori <i>et al.</i>, 2004)
The essential prerequisite for any further pharmaceutical and pharmacological
evaluation of gold(III) complexes is to make them stabilized.Therefore,
selection of suitable ligands to achieve stable gold(III) complexes is of
great importance. DPA add its derivatives are very popular ligands in
coordination chemistry, (Fuchita,<i>et al.</i>, 1985) in this paper we
synthesized its gold(III) complex. UV-vis and ^1^H NMR data showed that the
resulting complex exhibited reasonable stability at physiologically relevant
environment. The molecular structure, crystal data, selected bond lengths of
the title complex were shown in Fig. 1, Tables 1 and 2, respectively. In the
cationic part, the gold(III) center was bound by two N atoms of DPA and two Cl
atoms. All the Au---N and Au---Cl bond lengths are in the expected regions for
gold(III) complexes.(Messori <i>et al.</i>, 2002) The mean deviation from the
best N2Cl2Au plane [Au(1), N(1), N(1 A), Cl(1), Cl(1 A)] is 0.035 angstrom.
The dihedral angel between the coordination palne and the pyridinyl plane is
45.3 degree. There are two kind of hydrogen bonds: one is between the bound Cl
and the hydrogen in the pyridine ring, which bridge the cations into
one-dimensional ladder.The other is between the unbound cl and the hydrogen on
the unbound nitrogen. The unbound cl anion also has very short contact with
the Au center(3.037 angstrom),which will link the chains into two-dimensional
sheet together with the latter type of hydrogen bonds. The whole crystal are
composed of these sheets and the distance between two nearest layers is
3.3angstrom. Biological activity data showed that AuDPA has promising <i>in
vitro</i> cytotoxicity against A-549 and HCT-116 tumor cell lines.
;

_publ_section_exptl_prep         
;
The title compound was prepared by stirred a mixture of 34 mg DPA in 5 ml THF
and 80 mg HAuCl4 in 2 ml H~2~O at room temperature for 12 h, yellow
precipitate could be obtained and collected by filtration. Red crystals
suitable for X-ray analysis were obtained by slow evaporation from CH~3~CN
solution.Yield: 58%. Spectroscopic analysis: ^1^H NMR (CD~3~SOCD~3~, \d,
p.p.m.): 8.71(d, 2H, J = 6.3 Hz), 8.26 (t, 2H, J = 7.7 Hz), 7.60 (d, 2H, J =
8.3 Hz), 7.54 (t, 2H, J = 6.73 Hz). elemental analyses, calculated for
C~10~H~9~N~3~Cl~3~Au: C 25.31, H 1.91, N 8.86%; found: C 25.96, H 1.12, N
8.48%. ESI-MS (+P) m/<i>z</i>=438.1.
;

_publ_section_exptl_refinement   
;
The structure of the complex was solved with Patterson methods to locate all
the non-hydrogen atoms from the trial structure and then refined
anisotropically with <i>SHELXTL</i> using full-matrix least-squares procedure.
All the hydrogen atoms were geometrically fixed at calculated positions.
;

_publ_section_acknowledgements   
;
We are grateful for the financial supports from the National Natural Science
Foundation of China (Grants 20231010, 20228102 and 30370351) and the Natural
Science Foundation of Jiangsu Province (BK 2005209).
;

_publ_section_references         
;
1) C. F. Shaw, III, Chem. Rev. 99 (1999) 2589 2) L. Messori, G. Marcon, Met.
Ions Biol. Syst. 42 (2004) 385 3) Y.Fuchita, H.Ieda, Y.Tsunemune,
J.Kinoshita-Nagaoka,H.Kawano J.Chem.Soc.,Dalton Trans., 1985, 791 4) L.
Messori, F. Abbate, P. Orioli, C. Tempi, G. Marcon, Chem. Commun. (2002) 612
;

_publ_section_table_legends      
;
Table 1. Selected geometric parameters (\%A, \%).

Table 2. Hydrogen-bonding geometry (\%A, \%).
;

_publ_section_figure_captions    
;
Fig. 1. molecular structure of the title complex. Displacement ellipsoids are
drawn at the 30% probability level. H atomsare represented by circles of
arbitrary size.

Fig. 2. Packing diagram of the gold(III) complex. 

Fig. 3 (top) Layed structure in the lattice; (below) one layer along <i>a</i>
axis.
;

#==========================================================================


_chemical_name_systematic        
;
 (2,2-dipyridinylamine)gold(III) chloride
;
_chemical_name_common            AuDPA
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 Au Cl2 N3, Cl'
_chemical_formula_sum            'C10 H9 Au Cl3 N3'

_chemical_formula_weight         474.52

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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pnma '
_symmetry_space_group_name_Hall  '-P 2ac 2n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.549(4)
_cell_length_b                   12.313(4)
_cell_length_c                   8.200(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1267.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3897
_cell_measurement_theta_min      2.318
_cell_measurement_theta_max      28.007

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    12.222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.043
_exptl_absorpt_correction_T_max  0.141
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            6226
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1299
_reflns_number_gt                1238
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.2000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1299
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_restrained_S_all      1.211
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au -0.01457(3) 0.2500 0.79813(3) 0.02220(17) Uani 1 2 d S . .
C1 C 0.0960(4) 0.3501(4) 0.5219(6) 0.0230(11) Uani 1 1 d . . .
C2 C 0.1337(4) 0.4368(4) 0.4301(6) 0.0256(12) Uani 1 1 d . . .
H2 H 0.1439 0.4291 0.3184 0.031 Uiso 1 1 calc R . .
C3 C 0.1557(5) 0.5326(6) 0.5039(7) 0.0342(14) Uani 1 1 d . . .
H3 H 0.1814 0.5907 0.4432 0.041 Uiso 1 1 calc R . .
C4 C 0.1395(5) 0.5437(5) 0.6725(7) 0.0306(13) Uani 1 1 d . . .
H4 H 0.1568 0.6079 0.7259 0.037 Uiso 1 1 calc R . .
C5 C 0.0978(5) 0.4580(5) 0.7559(7) 0.0291(13) Uani 1 1 d . . .
H5 H 0.0852 0.4652 0.8671 0.035 Uiso 1 1 calc R . .
Cl1 Cl -0.12403(13) 0.12232(13) 0.90454(18) 0.0383(4) Uani 1 1 d . . .
Cl2 Cl 0.1446(2) 0.2500 0.0773(2) 0.0396(5) Uani 1 2 d S . .
N1 N 0.0740(4) 0.3628(4) 0.6822(5) 0.0215(10) Uani 1 1 d . . .
N2 N 0.0785(6) 0.2500 0.4495(7) 0.0283(15) Uani 1 2 d S . .
H2B H 0.1198 0.2500 0.3597 0.034 Uiso 1 2 d SR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Au1 0.0196(2) 0.0283(2) 0.0187(2) 0.000 0.00365(10) 0.000
C1 0.017(3) 0.030(3) 0.022(2) 0.000(2) 0.000(2) 0.006(2)
C2 0.020(3) 0.032(3) 0.024(3) 0.004(2) 0.004(2) 0.003(2)
C3 0.020(3) 0.039(3) 0.044(4) 0.010(3) 0.002(3) 0.000(3)
C4 0.029(4) 0.027(3) 0.036(3) 0.000(2) -0.006(3) -0.003(3)
C5 0.028(3) 0.035(3) 0.025(2) -0.007(2) -0.006(3) 0.003(3)
Cl1 0.0358(9) 0.0430(9) 0.0360(8) 0.0051(6) 0.0115(7) -0.0096(7)
Cl2 0.0457(14) 0.0497(13) 0.0234(9) 0.000 -0.0026(9) 0.000
N1 0.017(2) 0.027(2) 0.021(2) 0.0025(17) 0.0029(17) -0.001(2)
N2 0.034(4) 0.030(4) 0.021(3) 0.000 0.007(3) 0.000

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 N1 2.016(5) 7_565 ?
Au1 N1 2.016(5) . ?
Au1 Cl1 2.2627(15) . ?
Au1 Cl1 2.2627(15) 7_565 ?
Au1 Cl2 3.038(2) 1_556 ?
C1 N1 1.352(6) . ?
C1 N2 1.385(6) . ?
C1 C2 1.390(8) . ?
C2 C3 1.354(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.404(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(9) . ?
C4 H4 0.9300 . ?
C5 N1 1.352(8) . ?
C5 H5 0.9300 . ?
N2 C1 1.385(6) 7_565 ?
N2 H2B 0.9000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Au1 N1 87.0(3) 7_565 . ?
N1 Au1 Cl1 92.17(14) 7_565 . ?
N1 Au1 Cl1 174.11(13) . . ?
N1 Au1 Cl1 174.11(13) 7_565 7_565 ?
N1 Au1 Cl1 92.17(14) . 7_565 ?
Cl1 Au1 Cl1 88.02(9) . 7_565 ?
N1 Au1 Cl2 89.61(13) 7_565 1_556 ?
N1 Au1 Cl2 89.61(13) . 1_556 ?
Cl1 Au1 Cl2 96.23(5) . 1_556 ?
Cl1 Au1 Cl2 96.23(5) 7_565 1_556 ?
N1 C1 N2 119.2(5) . . ?
N1 C1 C2 120.5(5) . . ?
N2 C1 C2 120.3(5) . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.7(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 118.3(6) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 122.2(5) . . ?
N1 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 N1 C1 119.3(5) . . ?
C5 N1 Au1 120.5(4) . . ?
C1 N1 Au1 119.4(4) . . ?
C1 N2 C1 125.6(6) . 7_565 ?
C1 N2 H2B 105.1 . . ?
C1 N2 H2B 105.1 7_565 . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 4.6(9) . . . . ?
N2 C1 C2 C3 -176.6(6) . . . . ?
C1 C2 C3 C4 -0.4(9) . . . . ?
C2 C3 C4 C5 -2.6(10) . . . . ?
C3 C4 C5 N1 1.5(10) . . . . ?
C4 C5 N1 C1 2.7(9) . . . . ?
C4 C5 N1 Au1 -167.4(5) . . . . ?
N2 C1 N1 C5 175.4(6) . . . . ?
C2 C1 N1 C5 -5.7(8) . . . . ?
N2 C1 N1 Au1 -14.4(7) . . . . ?
C2 C1 N1 Au1 164.4(4) . . . . ?
N1 Au1 N1 C5 -145.9(4) 7_565 . . . ?
Cl1 Au1 N1 C5 40.0(4) 7_565 . . . ?
Cl2 Au1 N1 C5 -56.3(4) 1_556 . . . ?
N1 Au1 N1 C1 44.1(5) 7_565 . . . ?
Cl1 Au1 N1 C1 -130.1(4) 7_565 . . . ?
Cl2 Au1 N1 C1 133.7(4) 1_556 . . . ?
N1 C1 N2 C1 -37.2(11) . . . 7_565 ?
C2 C1 N2 C1 144.0(6) . . . 7_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B Cl2 0.90 2.34 3.162(6) 152.5 .
C5 H5 Cl1 0.93 2.74 3.458(6) 135.1 3_557

loop_
_publ_manuscript_incl_extra_item
'_geom_extra_tableA_col_1'
'_geom_extra_tableA_col_2'
'_geom_extra_tableA_col_3'
'_geom_extra_tableA_col_4'
'_geom_extra_table_head_A'


loop_
_geom_extra_tableA_col_1
_geom_extra_tableA_col_2
_geom_extra_tableA_col_3
_geom_extra_tableA_col_4
Au(1)---N(1A) 2.015(5) Au(1)--Cl(1A) 2.2628(16)
'Au(1)---N(1) ' 2.015(5) Au(1)--Cl(1) 2.2628(16)
N(1A)--Au(1)--N(1) 87.0(3) N(1A)--Au(1)--Cl(1) 92.18(15)
N(1)--Au(1)--Cl(1) 174.11(13) N(1A)--Au(1)--Cl(1A) 174.11(13)
N(1)--Au(1)--Cl(1A) 92.18(15) Cl(1)--Au(1)--Cl(1A) 88.02(9)

_geom_extra_table_head_A         
;
Selected geometric parameters (\%A, \%)
;

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.508
_refine_diff_density_min         -1.609
_refine_diff_density_rms         0.192

#   End of CIF   ============================================================


# Formatted by publCIF