# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
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data_732

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 Au N4 O3 P S'
_chemical_formula_sum            'C19 H14 Au N4 O3 P S'
_chemical_formula_weight         606.34

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'
P P 0.1023 0.0942 '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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   13.79810(10)
_cell_length_b                   13.08130(10)
_cell_length_c                   22.1996(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.0696(5)
_cell_angle_gamma                90
_cell_volume                     4006.27(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      29.15

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.011
_exptl_crystal_F_000             2320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    7.557
_shelx_estimated_absorpt_T_min   0.177
_shelx_estimated_absorpt_T_max   0.464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5156
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22205
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.835
_diffrn_reflns_theta_max         29.160
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5371
_reflns_number_gt                4612
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SIR2011 (Burla et al., 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
;
SHELXL-2013 (Sheldrick, 2013),
PLATON (Spek, 2009)
;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+3.2558P] where P=(Fo²+2Fc²)/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         5371
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0505
_refine_ls_wR_factor_gt          0.0484
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.39934(2) 0.42716(2) 0.29258(2) 0.03783(4) Uani 1 1 d . . . . .
S1 S 0.52526(5) 0.48695(6) 0.35250(3) 0.04493(16) Uani 1 1 d . . . . .
N1 N 0.59127(15) 0.38819(17) 0.45273(10) 0.0391(5) Uani 1 1 d . . . . .
N2 N 0.56764(19) 0.3093(2) 0.48958(12) 0.0541(6) Uani 1 1 d . . . . .
N3 N 0.48680(19) 0.2739(2) 0.46880(13) 0.0595(7) Uani 1 1 d . . . . .
N4 N 0.45541(16) 0.32617(19) 0.41930(11) 0.0477(6) Uani 1 1 d . . . . .
C5 C 0.52160(18) 0.3975(2) 0.40954(12) 0.0368(5) Uani 1 1 d . . . . .
C6 C 0.6813(2) 0.44094(19) 0.46047(12) 0.0386(6) Uani 1 1 d . . . . .
C7 C 0.6822(2) 0.5453(2) 0.46709(16) 0.0561(8) Uani 1 1 d . . . . .
H7 H 0.6246 0.5822 0.4671 0.067 Uiso 1 1 calc R U . . .
C8 C 0.7711(3) 0.5948(3) 0.47377(18) 0.0698(10) Uani 1 1 d . . . . .
H8 H 0.7732 0.6656 0.4773 0.084 Uiso 1 1 calc R U . . .
C9 C 0.8550(3) 0.5403(3) 0.47510(17) 0.0659(9) Uani 1 1 d . . . . .
H9 H 0.9140 0.5740 0.4800 0.079 Uiso 1 1 calc R U . . .
C10 C 0.8532(2) 0.4361(2) 0.46920(18) 0.0598(9) Uani 1 1 d . . . . .
H10 H 0.9108 0.3992 0.4705 0.072 Uiso 1 1 calc R U . . .
C11 C 0.7659(2) 0.3859(2) 0.46135(14) 0.0481(7) Uani 1 1 d . . . . .
H11 H 0.7645 0.3153 0.4567 0.058 Uiso 1 1 calc R U . . .
P1 P 0.26223(4) 0.37161(5) 0.24720(3) 0.03371(13) Uani 1 1 d . . . . .
O11 O 0.19422(13) 0.22716(16) 0.16873(10) 0.0523(5) Uani 1 1 d . . . . .
C12 C 0.27535(18) 0.27048(19) 0.19383(12) 0.0365(5) Uani 1 1 d . . . . .
C13 C 0.3548(2) 0.2254(2) 0.17190(13) 0.0470(6) Uani 1 1 d . . . . .
H13 H 0.4189 0.2412 0.1817 0.056 Uiso 1 1 calc R U . . .
C14 C 0.3220(2) 0.1493(2) 0.13104(14) 0.0557(8) Uani 1 1 d . . . . .
H14 H 0.3603 0.1056 0.1086 0.067 Uiso 1 1 calc R U . . .
C15 C 0.2259(2) 0.1523(3) 0.13110(14) 0.0577(8) Uani 1 1 d . . . . .
H15 H 0.1857 0.1093 0.1086 0.069 Uiso 1 1 calc R U . . .
O21 O 0.09750(15) 0.4504(2) 0.20038(14) 0.0785(9) Uani 1 1 d . . . . .
C22 C 0.19241(18) 0.4702(2) 0.21157(12) 0.0381(5) Uani 1 1 d . . . . .
C23 C 0.2129(2) 0.5652(2) 0.19523(16) 0.0542(8) Uani 1 1 d . . . . .
H23 H 0.2733 0.5966 0.1977 0.065 Uiso 1 1 calc R U . . .
C24 C 0.1259(3) 0.6099(3) 0.17333(16) 0.0600(8) Uani 1 1 d . . . . .
H24 H 0.1174 0.6762 0.1590 0.072 Uiso 1 1 calc R U . . .
C25 C 0.0600(3) 0.5390(3) 0.1774(2) 0.0821(13) Uani 1 1 d . . . . .
H25 H -0.0046 0.5478 0.1660 0.099 Uiso 1 1 calc R U . . .
O31 O 0.09775(14) 0.28217(17) 0.28743(9) 0.0533(5) Uani 1 1 d . . . . .
C32 C 0.18467(18) 0.3243(2) 0.30424(12) 0.0382(5) Uani 1 1 d . . . . .
C33 C 0.1925(2) 0.3284(2) 0.36438(13) 0.0507(7) Uani 1 1 d . . . . .
H33 H 0.2451 0.3533 0.3868 0.061 Uiso 1 1 calc R U . . .
C34 C 0.1061(2) 0.2878(3) 0.38739(15) 0.0583(8) Uani 1 1 d . . . . .
H34 H 0.0906 0.2804 0.4277 0.070 Uiso 1 1 calc R U . . .
C35 C 0.0515(2) 0.2623(3) 0.34013(16) 0.0599(9) Uani 1 1 d . . . . .
H35 H -0.0104 0.2345 0.3424 0.072 Uiso 1 1 calc R U . . .


_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 P1 2.2475(6) . ?
Au1 S1 2.3051(7) . ?
S1 C5 1.726(3) . ?
N1 C5 1.350(3) . ?
N1 N2 1.361(3) . ?
N1 C6 1.428(3) . ?
N2 N3 1.285(4) . ?
N3 N4 1.359(4) . ?
N4 C5 1.326(3) . ?
C6 C11 1.371(4) . ?
C6 C7 1.374(4) . ?
C7 C8 1.393(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.359(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
P1 C32 1.784(3) . ?
P1 C22 1.786(3) . ?
P1 C12 1.787(3) . ?
O11 C12 1.364(3) . ?
O11 C15 1.364(4) . ?
C12 C13 1.343(4) . ?
C13 C14 1.416(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.325(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
O21 C22 1.353(3) . ?
O21 C25 1.364(4) . ?
C22 C23 1.326(4) . ?
C23 C24 1.413(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.302(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
O31 C32 1.366(3) . ?
O31 C35 1.368(4) . ?
C32 C33 1.339(4) . ?
C33 C34 1.410(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.324(5) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?

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
P1 Au1 S1 170.93(3) . . ?
C5 S1 Au1 99.28(9) . . ?
C5 N1 N2 108.6(2) . . ?
C5 N1 C6 130.4(2) . . ?
N2 N1 C6 120.8(2) . . ?
N3 N2 N1 105.9(2) . . ?
N2 N3 N4 111.7(2) . . ?
C5 N4 N3 106.0(2) . . ?
N4 C5 N1 107.7(2) . . ?
N4 C5 S1 128.8(2) . . ?
N1 C5 S1 123.5(2) . . ?
C11 C6 C7 120.9(3) . . ?
C11 C6 N1 119.1(2) . . ?
C7 C6 N1 120.0(3) . . ?
C6 C7 C8 118.7(3) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 119.5(3) . . ?
C6 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C32 P1 C22 103.83(12) . . ?
C32 P1 C12 106.47(13) . . ?
C22 P1 C12 107.55(12) . . ?
C32 P1 Au1 107.76(9) . . ?
C22 P1 Au1 114.05(9) . . ?
C12 P1 Au1 116.21(8) . . ?
C12 O11 C15 106.1(2) . . ?
C13 C12 O11 109.8(2) . . ?
C13 C12 P1 131.2(2) . . ?
O11 C12 P1 119.05(18) . . ?
C12 C13 C14 106.7(3) . . ?
C12 C13 H13 126.6 . . ?
C14 C13 H13 126.6 . . ?
C15 C14 C13 106.6(3) . . ?
C15 C14 H14 126.7 . . ?
C13 C14 H14 126.7 . . ?
C14 C15 O11 110.8(3) . . ?
C14 C15 H15 124.6 . . ?
O11 C15 H15 124.6 . . ?
C22 O21 C25 105.4(3) . . ?
C23 C22 O21 109.9(3) . . ?
C23 C22 P1 133.0(2) . . ?
O21 C22 P1 117.1(2) . . ?
C22 C23 C24 107.3(3) . . ?
C22 C23 H23 126.4 . . ?
C24 C23 H23 126.4 . . ?
C25 C24 C23 105.7(3) . . ?
C25 C24 H24 127.1 . . ?
C23 C24 H24 127.1 . . ?
C24 C25 O21 111.7(3) . . ?
C24 C25 H25 124.1 . . ?
O21 C25 H25 124.1 . . ?
C32 O31 C35 105.3(2) . . ?
C33 C32 O31 110.1(2) . . ?
C33 C32 P1 131.0(2) . . ?
O31 C32 P1 118.8(2) . . ?
C32 C33 C34 107.0(3) . . ?
C32 C33 H33 126.5 . . ?
C34 C33 H33 126.5 . . ?
C35 C34 C33 106.3(3) . . ?
C35 C34 H34 126.8 . . ?
C33 C34 H34 126.8 . . ?
C34 C35 O31 111.2(3) . . ?
C34 C35 H35 124.4 . . ?
O31 C35 H35 124.4 . . ?

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
C5 N1 N2 N3 -0.2(3) . . . . ?
C6 N1 N2 N3 -175.6(3) . . . . ?
N1 N2 N3 N4 0.0(3) . . . . ?
N2 N3 N4 C5 0.1(3) . . . . ?
N3 N4 C5 N1 -0.3(3) . . . . ?
N3 N4 C5 S1 178.4(2) . . . . ?
N2 N1 C5 N4 0.3(3) . . . . ?
C6 N1 C5 N4 175.1(2) . . . . ?
N2 N1 C5 S1 -178.50(19) . . . . ?
C6 N1 C5 S1 -3.7(4) . . . . ?
Au1 S1 C5 N4 -9.1(3) . . . . ?
Au1 S1 C5 N1 169.4(2) . . . . ?
C5 N1 C6 C11 -120.4(3) . . . . ?
N2 N1 C6 C11 53.9(4) . . . . ?
C5 N1 C6 C7 59.8(4) . . . . ?
N2 N1 C6 C7 -125.9(3) . . . . ?
C11 C6 C7 C8 1.0(5) . . . . ?
N1 C6 C7 C8 -179.2(3) . . . . ?
C6 C7 C8 C9 -1.5(6) . . . . ?
C7 C8 C9 C10 0.7(6) . . . . ?
C8 C9 C10 C11 0.6(6) . . . . ?
C7 C6 C11 C10 0.2(5) . . . . ?
N1 C6 C11 C10 -179.6(3) . . . . ?
C9 C10 C11 C6 -1.0(5) . . . . ?
C15 O11 C12 C13 1.0(3) . . . . ?
C15 O11 C12 P1 -179.1(2) . . . . ?
C32 P1 C12 C13 -125.8(3) . . . . ?
C22 P1 C12 C13 123.4(3) . . . . ?
Au1 P1 C12 C13 -5.8(3) . . . . ?
C32 P1 C12 O11 54.2(2) . . . . ?
C22 P1 C12 O11 -56.6(2) . . . . ?
Au1 P1 C12 O11 174.20(17) . . . . ?
O11 C12 C13 C14 -0.3(3) . . . . ?
P1 C12 C13 C14 179.7(2) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 O11 1.1(4) . . . . ?
C12 O11 C15 C14 -1.3(4) . . . . ?
C25 O21 C22 C23 -1.2(4) . . . . ?
C25 O21 C22 P1 175.8(3) . . . . ?
C32 P1 C22 C23 133.6(3) . . . . ?
C12 P1 C22 C23 -113.8(3) . . . . ?
Au1 P1 C22 C23 16.6(4) . . . . ?
C32 P1 C22 O21 -42.6(3) . . . . ?
C12 P1 C22 O21 70.0(3) . . . . ?
Au1 P1 C22 O21 -159.6(2) . . . . ?
O21 C22 C23 C24 1.2(4) . . . . ?
P1 C22 C23 C24 -175.3(3) . . . . ?
C22 C23 C24 C25 -0.7(4) . . . . ?
C23 C24 C25 O21 -0.1(5) . . . . ?
C22 O21 C25 C24 0.8(5) . . . . ?
C35 O31 C32 C33 1.2(3) . . . . ?
C35 O31 C32 P1 -174.5(2) . . . . ?
C22 P1 C32 C33 -113.2(3) . . . . ?
C12 P1 C32 C33 133.4(3) . . . . ?
Au1 P1 C32 C33 8.1(3) . . . . ?
C22 P1 C32 O31 61.4(2) . . . . ?
C12 P1 C32 O31 -52.0(2) . . . . ?
Au1 P1 C32 O31 -177.35(18) . . . . ?
O31 C32 C33 C34 -0.6(3) . . . . ?
P1 C32 C33 C34 174.4(2) . . . . ?
C32 C33 C34 C35 -0.3(4) . . . . ?
C33 C34 C35 O31 1.1(4) . . . . ?
C32 O31 C35 C34 -1.4(4) . . . . ?

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
C34 H34 N3 0.93 2.65 3.555(4) 165. 7_556
C35 H35 O11 0.93 2.55 3.423(4) 157. 2

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.080

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1027451'
