# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

_publ_contact_author_name        'Angela Casini'
_publ_contact_author_email       ANGELA.CASINI@EPFL.CH

_publ_section_title              
;
Synthesis, characterization and biological properties
of gold(III) compounds with modified bipyridine and bipyridylamine ligands
;
loop_
_publ_author_name
'Angela Casini'
'Mariam Celine Diawara'
'Paul Dyson'
'Michael Gratzel'
'Rosario Scopelliti'
;
S.Zakeeruddin
;

# Attachment 'compound2.cif'

data_ac01
_database_code_depnum_ccdc_archive 'CCDC 750304'
#TrackingRef 'compound2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Au Cl2 N2, F6 P'
_chemical_formula_sum            'C12 H12 Au Cl2 F6 N2 P'
_chemical_formula_weight         597.07

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.6946(4)
_cell_length_b                   11.6360(5)
_cell_length_c                   19.5951(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.075(6)
_cell_angle_gamma                90.00
_cell_volume                     1721.77(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    11414
_cell_measurement_theta_min      2.6883
_cell_measurement_theta_max      27.3345

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    9.005
_exptl_absorpt_correction_T_min  0.096
_exptl_absorpt_correction_T_max  0.259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      140(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  'Oxford Diffraction, KM4/Sapphire CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.2812
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13947
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3578
_reflns_number_gt                3496
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0573P)^2^+30.5639P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3578
_refine_ls_number_parameters     274
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.042
_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 0.25235(7) 0.32438(4) 0.61218(2) 0.02649(14) Uani 1 1 d . . .
Cl1 Cl 0.2433(6) 0.2819(3) 0.49926(17) 0.0495(10) Uani 1 1 d . . .
Cl2 Cl 0.2550(7) 0.1352(3) 0.6356(2) 0.0523(10) Uani 1 1 d . . .
N1 N 0.2608(13) 0.3749(8) 0.7119(4) 0.0201(19) Uani 1 1 d . . .
N2 N 0.2487(15) 0.4971(7) 0.5981(4) 0.025(2) Uani 1 1 d . . .
C1 C 0.2748(19) 0.3036(10) 0.7673(7) 0.035(3) Uani 1 1 d . . .
H1 H 0.2791 0.2228 0.7607 0.043 Uiso 1 1 calc R . .
C2 C 0.2827(18) 0.3470(11) 0.8328(6) 0.034(3) Uani 1 1 d . . .
H2 H 0.2888 0.2958 0.8710 0.040 Uiso 1 1 calc R . .
C3 C 0.282(2) 0.4633(13) 0.8441(6) 0.039(3) Uani 1 1 d . . .
C4 C 0.2693(18) 0.5366(11) 0.7864(6) 0.030(3) Uani 1 1 d . . .
H4 H 0.2661 0.6175 0.7922 0.035 Uiso 1 1 calc R . .
C5 C 0.2615(15) 0.4899(9) 0.7216(5) 0.020(2) Uani 1 1 d . . .
C6 C 0.286(3) 0.5168(13) 0.9148(6) 0.052(4) Uani 1 1 d . . .
H6A H 0.1759 0.5595 0.9143 0.078 Uiso 1 1 calc R . .
H6B H 0.3870 0.5694 0.9258 0.078 Uiso 1 1 calc R . .
H6C H 0.2975 0.4562 0.9501 0.078 Uiso 1 1 calc R . .
C7 C 0.2497(16) 0.5574(9) 0.6578(5) 0.021(2) Uani 1 1 d . . .
C8 C 0.2406(19) 0.6761(10) 0.6550(6) 0.031(3) Uani 1 1 d . . .
H8 H 0.2416 0.7186 0.6965 0.037 Uiso 1 1 calc R . .
C9 C 0.230(2) 0.7339(10) 0.5919(6) 0.035(3) Uani 1 1 d . . .
C10 C 0.234(2) 0.6685(12) 0.5332(6) 0.042(3) Uani 1 1 d . . .
H10 H 0.2304 0.7050 0.4896 0.051 Uiso 1 1 calc R . .
C11 C 0.244(2) 0.5484(11) 0.5382(6) 0.038(3) Uani 1 1 d . . .
H11 H 0.2472 0.5039 0.4978 0.045 Uiso 1 1 calc R . .
C12 C 0.214(4) 0.8613(10) 0.5888(8) 0.064(6) Uani 1 1 d . . .
H12A H 0.3227 0.8944 0.5781 0.096 Uiso 1 1 calc R . .
H12B H 0.1958 0.8905 0.6338 0.096 Uiso 1 1 calc R . .
H12C H 0.1130 0.8830 0.5526 0.096 Uiso 1 1 calc R . .
P1 P -0.2425(4) 0.4227(3) 0.67400(16) 0.0311(7) Uani 1 1 d DU . .
F1A F -0.360(2) 0.5252(16) 0.6878(13) 0.088(6) Uani 0.663(16) 1 d PDU A 1
F2A F -0.121(2) 0.491(2) 0.6346(10) 0.078(6) Uani 0.663(16) 1 d PDU A 1
F3A F -0.376(2) 0.400(2) 0.6020(7) 0.066(5) Uani 0.663(16) 1 d PDU A 1
F4A F -0.140(2) 0.3122(15) 0.6568(12) 0.082(6) Uani 0.663(16) 1 d PDU A 1
F5A F -0.366(2) 0.3348(17) 0.7045(11) 0.079(6) Uani 0.663(16) 1 d PDU A 1
F6A F -0.113(3) 0.430(2) 0.7445(7) 0.070(6) Uani 0.663(16) 1 d PDU A 1
F1B F -0.362(4) 0.447(5) 0.7285(14) 0.075(10) Uani 0.337(16) 1 d PDU A 2
F2B F -0.146(3) 0.5412(19) 0.696(2) 0.066(8) Uani 0.337(16) 1 d PDU A 2
F3B F -0.368(3) 0.490(3) 0.6165(16) 0.060(8) Uani 0.337(16) 1 d PDU A 2
F4B F -0.101(3) 0.406(4) 0.6275(11) 0.052(8) Uani 0.337(16) 1 d PDU A 2
F5B F -0.357(5) 0.319(2) 0.646(2) 0.077(9) Uani 0.337(16) 1 d PDU A 2
F6B F -0.110(4) 0.363(4) 0.733(2) 0.075(11) Uani 0.337(16) 1 d PDU A 2

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 0.0407(2) 0.01386(18) 0.0259(2) -0.00551(17) 0.0089(2) 0.0002(2)
Cl1 0.088(3) 0.0314(16) 0.0319(15) -0.0168(14) 0.0175(16) -0.0013(17)
Cl2 0.093(3) 0.0127(12) 0.0551(19) -0.0059(13) 0.024(2) -0.0018(18)
N1 0.031(5) 0.011(4) 0.019(4) 0.000(3) 0.007(4) -0.002(4)
N2 0.039(5) 0.017(4) 0.021(4) -0.007(3) 0.013(4) -0.005(4)
C1 0.052(8) 0.017(5) 0.036(6) 0.012(5) 0.006(6) -0.004(5)
C2 0.041(7) 0.035(7) 0.024(5) 0.016(5) 0.004(5) 0.000(5)
C3 0.055(9) 0.044(8) 0.017(5) 0.002(5) 0.001(5) -0.009(7)
C4 0.047(7) 0.022(6) 0.020(5) -0.006(4) 0.007(5) -0.004(5)
C5 0.030(6) 0.011(4) 0.018(5) -0.004(4) 0.001(4) 0.001(4)
C6 0.096(14) 0.038(7) 0.021(6) 0.001(5) 0.008(8) -0.007(9)
C7 0.030(6) 0.015(5) 0.018(4) -0.003(4) 0.004(4) -0.001(5)
C8 0.059(8) 0.017(5) 0.017(5) -0.004(4) 0.011(5) 0.000(6)
C9 0.062(9) 0.015(5) 0.026(6) -0.002(4) 0.003(6) 0.003(6)
C10 0.079(11) 0.031(7) 0.021(5) 0.005(5) 0.022(6) -0.001(8)
C11 0.070(10) 0.025(6) 0.022(5) -0.005(5) 0.019(6) -0.008(6)
C12 0.15(2) 0.007(5) 0.038(7) 0.002(5) 0.027(10) 0.007(9)
P1 0.0252(15) 0.0395(17) 0.0290(15) 0.0088(13) 0.0057(13) -0.0011(14)
F1A 0.055(9) 0.058(10) 0.139(16) -0.052(11) -0.011(11) 0.013(9)
F2A 0.040(8) 0.107(15) 0.082(12) 0.062(12) -0.003(8) -0.004(11)
F3A 0.049(9) 0.107(15) 0.041(7) -0.017(9) 0.007(7) -0.029(10)
F4A 0.039(8) 0.082(12) 0.122(14) -0.029(11) 0.008(9) 0.007(9)
F5A 0.047(8) 0.078(12) 0.101(13) 0.061(11) -0.011(9) -0.008(9)
F6A 0.046(9) 0.134(18) 0.027(6) -0.009(10) 0.000(6) 0.004(12)
F1B 0.046(15) 0.14(3) 0.044(14) -0.013(18) 0.020(12) 0.006(19)
F2B 0.025(12) 0.043(14) 0.13(2) -0.030(15) 0.012(13) -0.011(11)
F3B 0.030(12) 0.08(2) 0.069(17) 0.042(16) 0.007(14) -0.001(14)
F4B 0.033(13) 0.09(2) 0.030(11) 0.017(13) 0.005(9) 0.034(15)
F5B 0.074(18) 0.048(15) 0.11(2) -0.014(18) 0.022(18) -0.004(16)
F6B 0.033(14) 0.11(3) 0.08(2) 0.070(19) 0.009(15) 0.016(19)

_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 N2 2.027(9) . ?
Au1 N1 2.030(9) . ?
Au1 Cl2 2.248(3) . ?
Au1 Cl1 2.255(3) . ?
N1 C5 1.351(13) . ?
N1 C1 1.354(14) . ?
N2 C11 1.312(15) . ?
N2 C7 1.362(13) . ?
C1 C2 1.370(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.37(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(18) . ?
C3 C6 1.514(18) . ?
C4 C5 1.372(15) . ?
C4 H4 0.9500 . ?
C5 C7 1.465(15) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.383(15) . ?
C8 C9 1.396(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(17) . ?
C9 C12 1.488(16) . ?
C10 C11 1.402(19) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
P1 F5B 1.532(19) . ?
P1 F2A 1.541(13) . ?
P1 F6A 1.541(13) . ?
P1 F6B 1.548(18) . ?
P1 F3B 1.550(17) . ?
P1 F1A 1.550(13) . ?
P1 F4B 1.563(16) . ?
P1 F1B 1.565(17) . ?
P1 F4A 1.580(14) . ?
P1 F2B 1.583(17) . ?
P1 F5A 1.591(13) . ?
P1 F3A 1.599(12) . ?

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
N2 Au1 N1 80.8(3) . . ?
N2 Au1 Cl2 176.0(3) . . ?
N1 Au1 Cl2 95.2(3) . . ?
N2 Au1 Cl1 95.0(3) . . ?
N1 Au1 Cl1 175.8(3) . . ?
Cl2 Au1 Cl1 89.02(13) . . ?
C5 N1 C1 119.8(10) . . ?
C5 N1 Au1 114.9(7) . . ?
C1 N1 Au1 125.2(8) . . ?
C11 N2 C7 121.9(10) . . ?
C11 N2 Au1 124.7(8) . . ?
C7 N2 Au1 113.4(7) . . ?
N1 C1 C2 120.5(11) . . ?
N1 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C1 C2 C3 121.0(11) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 118.1(12) . . ?
C2 C3 C6 123.6(12) . . ?
C4 C3 C6 118.3(12) . . ?
C5 C4 C3 119.3(11) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 121.4(10) . . ?
N1 C5 C7 114.4(9) . . ?
C4 C5 C7 124.3(10) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 119.3(10) . . ?
N2 C7 C5 116.5(9) . . ?
C8 C7 C5 124.2(9) . . ?
C7 C8 C9 120.6(10) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 117.6(11) . . ?
C10 C9 C12 121.9(11) . . ?
C8 C9 C12 120.4(11) . . ?
C9 C10 C11 120.0(11) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
N2 C11 C10 120.5(11) . . ?
N2 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F5B P1 F2A 126(2) . . ?
F5B P1 F6A 126(2) . . ?
F2A P1 F6A 94.0(12) . . ?
F5B P1 F6B 99(3) . . ?
F2A P1 F6B 103.0(16) . . ?
F5B P1 F3B 85(2) . . ?
F2A P1 F3B 74.4(11) . . ?
F6A P1 F3B 146(2) . . ?
F6B P1 F3B 176(2) . . ?
F5B P1 F1A 110.8(16) . . ?
F2A P1 F1A 97.1(15) . . ?
F6A P1 F1A 95.5(12) . . ?
F6B P1 F1A 123(2) . . ?
F3B P1 F1A 55.6(17) . . ?
F5B P1 F4B 97(2) . . ?
F6A P1 F4B 97.3(12) . . ?
F6B P1 F4B 87(2) . . ?
F3B P1 F4B 92.7(15) . . ?
F1A P1 F4B 133.8(18) . . ?
F5B P1 F1B 91(2) . . ?
F2A P1 F1B 138(2) . . ?
F6A P1 F1B 75.0(14) . . ?
F6B P1 F1B 88(2) . . ?
F3B P1 F1B 92.1(19) . . ?
F1A P1 F1B 45.8(18) . . ?
F4B P1 F1B 171.8(18) . . ?
F5B P1 F4A 63.8(15) . . ?
F2A P1 F4A 86.1(12) . . ?
F6A P1 F4A 88.5(11) . . ?
F6B P1 F4A 60(2) . . ?
F3B P1 F4A 121.7(18) . . ?
F1A P1 F4A 174.6(10) . . ?
F4B P1 F4A 48.7(15) . . ?
F1B P1 F4A 133(2) . . ?
F5B P1 F2B 172(2) . . ?
F2A P1 F2B 52.4(16) . . ?
F6A P1 F2B 61.5(17) . . ?
F6B P1 F2B 89(2) . . ?
F3B P1 F2B 87(2) . . ?
F1A P1 F2B 62.7(12) . . ?
F4B P1 F2B 85.5(19) . . ?
F1B P1 F2B 88(2) . . ?
F4A P1 F2B 122.6(12) . . ?
F2A P1 F5A 169.6(14) . . ?
F6A P1 F5A 91.7(12) . . ?
F6B P1 F5A 77.8(16) . . ?
F3B P1 F5A 105.3(12) . . ?
F1A P1 F5A 91.0(12) . . ?
F4B P1 F5A 132.5(18) . . ?
F1B P1 F5A 52.1(19) . . ?
F4A P1 F5A 85.3(12) . . ?
F2B P1 F5A 137.9(17) . . ?
F5B P1 F3A 48.2(18) . . ?
F2A P1 F3A 89.4(10) . . ?
F6A P1 F3A 173.9(13) . . ?
F6B P1 F3A 143(2) . . ?
F1A P1 F3A 89.0(11) . . ?
F4B P1 F3A 82.4(12) . . ?
F1B P1 F3A 105.6(13) . . ?
F4A P1 F3A 86.7(11) . . ?
F2B P1 F3A 124.4(17) . . ?
F5A P1 F3A 84.2(10) . . ?

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
N2 Au1 N1 C5 -0.5(9) . . . . ?
Cl2 Au1 N1 C5 179.9(8) . . . . ?
N2 Au1 N1 C1 -176.9(11) . . . . ?
Cl2 Au1 N1 C1 3.5(11) . . . . ?
N1 Au1 N2 C11 179.4(13) . . . . ?
Cl1 Au1 N2 C11 -0.5(13) . . . . ?
N1 Au1 N2 C7 -1.3(9) . . . . ?
Cl1 Au1 N2 C7 178.9(9) . . . . ?
C5 N1 C1 C2 3(2) . . . . ?
Au1 N1 C1 C2 178.7(10) . . . . ?
N1 C1 C2 C3 -2(2) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C1 C2 C3 C6 178.4(16) . . . . ?
C2 C3 C4 C5 -1(2) . . . . ?
C6 C3 C4 C5 -178.5(14) . . . . ?
C1 N1 C5 C4 -2.5(19) . . . . ?
Au1 N1 C5 C4 -179.1(10) . . . . ?
C1 N1 C5 C7 178.7(11) . . . . ?
Au1 N1 C5 C7 2.1(14) . . . . ?
C3 C4 C5 N1 2(2) . . . . ?
C3 C4 C5 C7 -179.4(12) . . . . ?
C11 N2 C7 C8 2(2) . . . . ?
Au1 N2 C7 C8 -177.6(10) . . . . ?
C11 N2 C7 C5 -177.9(13) . . . . ?
Au1 N2 C7 C5 2.8(14) . . . . ?
N1 C5 C7 N2 -3.2(17) . . . . ?
C4 C5 C7 N2 178.0(12) . . . . ?
N1 C5 C7 C8 177.1(12) . . . . ?
C4 C5 C7 C8 -2(2) . . . . ?
N2 C7 C8 C9 0(2) . . . . ?
C5 C7 C8 C9 179.9(13) . . . . ?
C7 C8 C9 C10 -2(2) . . . . ?
C7 C8 C9 C12 177.9(17) . . . . ?
C8 C9 C10 C11 2(3) . . . . ?
C12 C9 C10 C11 -178.1(19) . . . . ?
C7 N2 C11 C10 -2(2) . . . . ?
Au1 N2 C11 C10 177.3(12) . . . . ?
C9 C10 C11 N2 0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         2.287
_refine_diff_density_min         -2.489
_refine_diff_density_rms         0.221

# Attachment 'compound3.cif'

data_ac02
_database_code_depnum_ccdc_archive 'CCDC 750305'
#TrackingRef 'compound3.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Au Cl2 N2 O2, F6 P'
_chemical_formula_sum            'C12 H12 Au Cl2 F6 N2 O2 P'
_chemical_formula_weight         629.07

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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           Monoclinic
_symmetry_space_group_name_H-M   'P 2/c'
_symmetry_space_group_name_Hall  '-P 2yc'

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

_cell_length_a                   7.8169(11)
_cell_length_b                   9.0950(7)
_cell_length_c                   13.1775(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.175(13)
_cell_angle_gamma                90.00
_cell_volume                     899.76(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    6542
_cell_measurement_theta_min      2.6959
_cell_measurement_theta_max      27.2697

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    8.630
_exptl_absorpt_correction_T_min  0.102
_exptl_absorpt_correction_T_max  0.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      140(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  'Oxford Diffraction, KM4/Sapphire CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.2812
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1821
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         26.34
_reflns_number_total             1821
_reflns_number_gt                1782
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0390P)^2^+79.8557P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1821
_refine_ls_number_parameters     121
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.2118
_refine_ls_wR_factor_gt          0.2114
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_restrained_S_all      1.227
_refine_ls_shift/su_max          0.000
_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 0.0000 0.08694(12) 0.2500 0.0164(3) Uani 1 2 d S . .
Cl1 Cl -0.1148(8) 0.2656(5) 0.1312(4) 0.0321(12) Uani 1 1 d . . .
O1 O -0.236(3) -0.4573(17) -0.0247(13) 0.040(4) Uani 1 1 d . . .
N1 N -0.093(2) -0.0789(19) 0.1475(13) 0.022(3) Uani 1 1 d . . .
C1 C -0.049(2) -0.2193(19) 0.1945(12) 0.013(3) Uani 1 1 d U . .
C2 C -0.095(3) -0.343(2) 0.1343(14) 0.020(4) Uani 1 1 d U . .
H2 H -0.0604 -0.4374 0.1639 0.024 Uiso 1 1 calc R . .
C3 C -0.194(3) -0.329(2) 0.0281(16) 0.026(5) Uani 1 1 d . . .
C4 C -0.239(3) -0.191(3) -0.0156(16) 0.028(5) Uani 1 1 d . . .
H4 H -0.3027 -0.1800 -0.0879 0.034 Uiso 1 1 calc R . .
C5 C -0.188(3) -0.072(2) 0.0492(16) 0.025(4) Uani 1 1 d . . .
H5 H -0.2241 0.0223 0.0204 0.030 Uiso 1 1 calc R . .
C6 C -0.345(4) -0.451(3) -0.1318(19) 0.047(7) Uani 1 1 d . . .
H6A H -0.4600 -0.4066 -0.1341 0.070 Uiso 1 1 calc R . .
H6B H -0.3639 -0.5510 -0.1609 0.070 Uiso 1 1 calc R . .
H6C H -0.2851 -0.3920 -0.1739 0.070 Uiso 1 1 calc R . .
P1 P -0.5000 -0.0974(8) 0.2500 0.0210(14) Uani 1 2 d S . .
F1 F -0.699(2) -0.096(3) 0.1757(12) 0.076(7) Uani 1 1 d . . .
F2 F -0.445(2) 0.034(3) 0.191(3) 0.163(19) Uani 1 1 d . . .
F3 F -0.444(2) -0.213(2) 0.1794(16) 0.072(6) Uani 1 1 d . . .

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 0.0272(6) 0.0054(4) 0.0161(5) 0.000 0.0053(4) 0.000
Cl1 0.050(3) 0.011(2) 0.033(3) 0.007(2) 0.009(2) 0.004(2)
O1 0.057(11) 0.018(8) 0.031(9) 0.002(6) -0.012(8) 0.003(8)
N1 0.028(9) 0.017(8) 0.018(8) -0.004(7) 0.003(7) -0.009(7)
C1 0.017(6) 0.014(7) 0.006(6) 0.005(5) 0.001(5) -0.002(6)
C2 0.025(7) 0.020(7) 0.010(7) 0.002(6) -0.001(6) 0.005(6)
C3 0.031(11) 0.017(10) 0.022(10) -0.005(8) -0.004(8) -0.007(9)
C4 0.033(11) 0.030(11) 0.019(10) 0.002(9) 0.003(8) -0.004(9)
C5 0.028(10) 0.019(10) 0.026(10) -0.002(8) 0.005(8) -0.002(9)
C6 0.074(19) 0.019(11) 0.030(13) 0.003(9) -0.013(13) -0.002(12)
P1 0.020(3) 0.020(3) 0.020(3) 0.000 0.003(3) 0.000
F1 0.025(8) 0.16(2) 0.039(8) 0.021(12) -0.001(7) -0.008(11)
F2 0.030(9) 0.11(2) 0.33(5) 0.18(3) 0.018(16) 0.002(11)
F3 0.052(10) 0.091(15) 0.087(14) -0.057(12) 0.043(10) -0.037(10)

_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 2.020(16) 2 ?
Au1 N1 2.020(16) . ?
Au1 Cl1 2.261(5) . ?
Au1 Cl1 2.261(5) 2 ?
O1 C3 1.35(2) . ?
O1 C6 1.43(3) . ?
N1 C5 1.30(3) . ?
N1 C1 1.42(2) . ?
C1 C2 1.37(3) . ?
C1 C1 1.45(3) 2 ?
C2 C3 1.40(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.38(3) . ?
C4 C5 1.37(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
P1 F3 1.549(18) . ?
P1 F3 1.549(18) 2_455 ?
P1 F2 1.553(19) . ?
P1 F2 1.553(19) 2_455 ?
P1 F1 1.593(14) . ?
P1 F1 1.593(14) 2_455 ?

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 83.4(10) 2 . ?
N1 Au1 Cl1 177.2(5) 2 . ?
N1 Au1 Cl1 94.3(5) . . ?
N1 Au1 Cl1 94.3(5) 2 2 ?
N1 Au1 Cl1 177.2(5) . 2 ?
Cl1 Au1 Cl1 88.1(3) . 2 ?
C3 O1 C6 117.8(17) . . ?
C5 N1 C1 118.5(17) . . ?
C5 N1 Au1 128.9(15) . . ?
C1 N1 Au1 112.5(11) . . ?
C2 C1 N1 119.8(15) . . ?
C2 C1 C1 124.4(10) . 2 ?
N1 C1 C1 115.8(9) . 2 ?
C1 C2 C3 119.1(18) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
O1 C3 C4 124.8(18) . . ?
O1 C3 C2 114.9(19) . . ?
C4 C3 C2 120.2(19) . . ?
C5 C4 C3 117.5(19) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
N1 C5 C4 125(2) . . ?
N1 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
F3 P1 F3 94.1(17) . 2_455 ?
F3 P1 F2 93.5(16) . . ?
F3 P1 F2 172.2(19) 2_455 . ?
F3 P1 F2 172.2(19) . 2_455 ?
F3 P1 F2 93.5(16) 2_455 2_455 ?
F2 P1 F2 79(3) . 2_455 ?
F3 P1 F1 91.7(12) . . ?
F3 P1 F1 89.0(11) 2_455 . ?
F2 P1 F1 92.5(12) . . ?
F2 P1 F1 86.7(13) 2_455 . ?
F3 P1 F1 89.0(11) . 2_455 ?
F3 P1 F1 91.7(11) 2_455 2_455 ?
F2 P1 F1 86.7(13) . 2_455 ?
F2 P1 F1 92.5(12) 2_455 2_455 ?
F1 P1 F1 179(2) . 2_455 ?

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 Au1 N1 C5 177(2) 2 . . . ?
Cl1 Au1 N1 C5 -1.3(19) . . . . ?
N1 Au1 N1 C1 -0.3(9) 2 . . . ?
Cl1 Au1 N1 C1 -178.9(12) . . . . ?
C5 N1 C1 C2 5(3) . . . . ?
Au1 N1 C1 C2 -177.0(14) . . . . ?
C5 N1 C1 C1 -177(2) . . . 2 ?
Au1 N1 C1 C1 1(2) . . . 2 ?
N1 C1 C2 C3 -4(3) . . . . ?
C1 C1 C2 C3 178(2) 2 . . . ?
C6 O1 C3 C4 -4(4) . . . . ?
C6 O1 C3 C2 177(2) . . . . ?
C1 C2 C3 O1 -179(2) . . . . ?
C1 C2 C3 C4 2(3) . . . . ?
O1 C3 C4 C5 179(2) . . . . ?
C2 C3 C4 C5 -2(3) . . . . ?
C1 N1 C5 C4 -5(3) . . . . ?
Au1 N1 C5 C4 177.4(17) . . . . ?
C3 C4 C5 N1 4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.34
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         5.340
_refine_diff_density_min         -6.986
_refine_diff_density_rms         0.506