# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_18
_audit_block_doi                 10.5517/cc1jd0c9
_database_code_depnum_ccdc_archive 'CCDC 1411720'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/ic502751s 2015
_audit_update_record             
;
2015-07-08 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H52 Au2 N8, 2(F6 P)'
_chemical_formula_sum            'C32 H52 Au2 F12 N8 P2'
_chemical_formula_weight         1232.69

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'
Au Au -2.0133 8.8022 '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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3753(7)
_cell_length_b                   10.8525(8)
_cell_length_c                   11.5698(8)
_cell_angle_alpha                113.079(4)
_cell_angle_beta                 90.440(4)
_cell_angle_gamma                115.080(3)
_cell_volume                     1061.59(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3380
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      29.13

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    7.064
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.3628
_exptl_absorpt_correction_T_max  0.7653
_exptl_absorpt_process_details   
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_diffrn_reflns_number            10919
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4166
_reflns_number_gt                3615
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0197P)²+46.8150P] 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         4166
_refine_ls_number_parameters     256
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.1768
_refine_ls_wR_factor_gt          0.1715
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.160
_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
C2 C 0.2693(16) 1.0768(16) 0.1058(14) 0.022(3) Uani 1 1 d U . .
C4 C 0.4889(18) 1.2672(18) 0.2179(15) 0.032(4) Uani 1 1 d . . .
H4 H 0.5838 1.3491 0.2394 0.038 Uiso 1 1 calc R . .
C5 C 0.4198(18) 1.2128(18) 0.2968(16) 0.032(4) Uani 1 1 d . . .
H5 H 0.4564 1.2481 0.3853 0.039 Uiso 1 1 calc R . .
C6 C 0.1722(17) 1.0077(19) 0.2867(17) 0.035(4) Uani 1 1 d U . .
H6A H 0.1685 1.0815 0.3691 0.042 Uiso 1 1 calc R . .
H6B H 0.0750 0.9531 0.2298 0.042 Uiso 1 1 calc R . .
C7 C 0.2010(18) 0.9021(19) 0.3105(15) 0.033(4) Uani 1 1 d U . .
H7A H 0.1430 0.8756 0.3725 0.040 Uiso 1 1 calc R . .
H7B H 0.3050 0.9516 0.3516 0.040 Uiso 1 1 calc R . .
C8 C 0.1669(18) 0.7542(19) 0.1902(15) 0.032(4) Uani 1 1 d . . .
H8A H 0.0606 0.6981 0.1555 0.038 Uiso 1 1 calc R . .
H8B H 0.2148 0.7810 0.1238 0.038 Uiso 1 1 calc R . .
C9 C 0.4312(18) 1.1979(18) -0.0202(16) 0.031(4) Uani 1 1 d . . .
H9A H 0.5071 1.3025 0.0031 0.037 Uiso 1 1 calc R . .
H9B H 0.3431 1.1807 -0.0712 0.037 Uiso 1 1 calc R . .
C10 C 0.485(2) 1.088(2) -0.1023(18) 0.043(4) Uani 1 1 d U . .
H10A H 0.5776 1.1113 -0.0559 0.065 Uiso 1 1 calc R . .
H10B H 0.4975 1.0963 -0.1831 0.065 Uiso 1 1 calc R . .
H10C H 0.4127 0.9842 -0.1209 0.065 Uiso 1 1 calc R . .
C12 C 0.0544(15) 0.2520(16) 0.2072(13) 0.019(3) Uani 1 1 d U . .
C14 C 0.1717(18) 0.3802(17) 0.4145(17) 0.030(3) Uani 1 1 d . . .
H14 H 0.1940 0.4113 0.5043 0.036 Uiso 1 1 calc R . .
C15 C 0.2547(19) 0.4429(18) 0.3475(15) 0.030(4) Uani 1 1 d . . .
H15 H 0.3486 0.5279 0.3799 0.036 Uiso 1 1 calc R . .
C16 C 0.2264(18) 0.3997(18) 0.1116(15) 0.028(3) Uani 1 1 d . . .
H16A H 0.1921 0.3066 0.0301 0.034 Uiso 1 1 calc R . .
H16B H 0.3341 0.4519 0.1298 0.034 Uiso 1 1 calc R . .
C17 C 0.1703(19) 0.5012(19) 0.0969(15) 0.034(4) Uani 1 1 d . . .
H17A H 0.2042 0.5229 0.0240 0.041 Uiso 1 1 calc R . .
H17B H 0.0627 0.4453 0.0741 0.041 Uiso 1 1 calc R . .
C18 C 0.2149(18) 0.6495(18) 0.2128(15) 0.030(3) Uani 1 1 d . . .
H18A H 0.3221 0.7023 0.2405 0.036 Uiso 1 1 calc R . .
H18B H 0.1733 0.6287 0.2838 0.036 Uiso 1 1 calc R . .
C19 C -0.0796(19) 0.1648(19) 0.3664(16) 0.033(3) Uani 1 1 d U . .
H19A H -0.0439 0.1487 0.4361 0.039 Uiso 1 1 calc R . .
H19B H -0.1351 0.0648 0.2920 0.039 Uiso 1 1 calc R . .
C20 C -0.181(2) 0.234(2) 0.4115(19) 0.051(5) Uani 1 1 d U . .
H20A H -0.1257 0.3348 0.4836 0.076 Uiso 1 1 calc R . .
H20B H -0.2594 0.1696 0.4393 0.076 Uiso 1 1 calc R . .
H20C H -0.2218 0.2439 0.3408 0.076 Uiso 1 1 calc R . .
Au Au 0.10433(7) 0.91366(7) -0.04801(6) 0.02301(19) Uani 1 1 d . . .
F1 F 0.4038(11) 0.4118(13) 0.8297(10) 0.052(3) Uani 1 1 d . . .
F2 F 0.2112(12) 0.4001(12) 0.7226(11) 0.044(3) Uani 1 1 d . . .
F3 F 0.1491(11) 0.1562(12) 0.5847(9) 0.046(3) Uani 1 1 d . . .
F4 F 0.3456(12) 0.1744(13) 0.6902(11) 0.047(3) Uani 1 1 d . . .
F5 F 0.1798(11) 0.2269(11) 0.7991(9) 0.037(2) Uani 1 1 d . . .
F6 F 0.3747(11) 0.3451(13) 0.6144(10) 0.047(3) Uani 1 1 d . . .
N1 N 0.2834(14) 1.0943(14) 0.2252(13) 0.027(3) Uani 1 1 d . . .
N3 N 0.3966(14) 1.1818(15) 0.0990(13) 0.030(3) Uani 1 1 d . . .
N11 N 0.1764(15) 0.3587(14) 0.2162(12) 0.027(3) Uani 1 1 d . . .
N13 N 0.0462(15) 0.2605(14) 0.3290(12) 0.026(3) Uani 1 1 d U . .
P P 0.2772(4) 0.2855(5) 0.7067(4) 0.0277(9) Uani 1 1 d . . .


_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
C2 N1 1.316(19) . ?
C2 N3 1.358(19) . ?
C2 Au 2.036(15) . ?
C4 C5 1.33(2) . ?
C4 N3 1.38(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.40(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.42(2) . ?
C6 N1 1.53(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.55(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C18 1.52(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.48(2) . ?
C9 C10 1.52(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 N11 1.271(19) . ?
C12 N13 1.381(18) . ?
C12 Au 2.046(14) 2_565 ?
C14 C15 1.32(2) . ?
C14 N13 1.38(2) . ?
C14 H14 0.9500 . ?
C15 N11 1.437(19) . ?
C15 H15 0.9500 . ?
C16 N11 1.473(19) . ?
C16 C17 1.51(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.51(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N13 1.48(2) . ?
C19 C20 1.52(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
Au C12 2.046(14) 2_565 ?
Au Au 3.3583(13) 2_575 ?
F1 P 1.595(10) . ?
F2 P 1.609(11) . ?
F3 P 1.601(10) . ?
F4 P 1.595(11) . ?
F5 P 1.604(9) . ?
F6 P 1.607(10) . ?

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 C2 N3 106.3(13) . . ?
N1 C2 Au 129.0(11) . . ?
N3 C2 Au 124.4(11) . . ?
C5 C4 N3 106.8(14) . . ?
C5 C4 H4 126.6 . . ?
N3 C4 H4 126.6 . . ?
C4 C5 N1 107.2(14) . . ?
C4 C5 H5 126.4 . . ?
N1 C5 H5 126.4 . . ?
C7 C6 N1 114.8(13) . . ?
C7 C6 H6A 108.6 . . ?
N1 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
N1 C6 H6B 108.6 . . ?
H6A C6 H6B 107.5 . . ?
C6 C7 C8 115.2(14) . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C18 C8 C7 115.2(13) . . ?
C18 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C18 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
N3 C9 C10 112.6(13) . . ?
N3 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N11 C12 N13 107.2(13) . . ?
N11 C12 Au 129.6(11) . 2_565 ?
N13 C12 Au 123.2(10) . 2_565 ?
C15 C14 N13 106.7(15) . . ?
C15 C14 H14 126.7 . . ?
N13 C14 H14 126.7 . . ?
C14 C15 N11 107.1(15) . . ?
C14 C15 H15 126.4 . . ?
N11 C15 H15 126.4 . . ?
N11 C16 C17 111.4(13) . . ?
N11 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N11 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C16 115.9(13) . . ?
C18 C17 H17A 108.3 . . ?
C16 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C16 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C17 C18 C8 114.2(13) . . ?
C17 C18 H18A 108.7 . . ?
C8 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C8 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
N13 C19 C20 112.5(14) . . ?
N13 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N13 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2 Au C12 177.3(6) . 2_565 ?
C2 Au Au 91.8(4) . 2_575 ?
C12 Au Au 90.6(4) 2_565 2_575 ?
C2 N1 C5 110.0(13) . . ?
C2 N1 C6 128.5(13) . . ?
C5 N1 C6 121.5(13) . . ?
C2 N3 C4 109.8(13) . . ?
C2 N3 C9 124.6(13) . . ?
C4 N3 C9 125.6(14) . . ?
C12 N11 C15 109.6(13) . . ?
C12 N11 C16 125.8(13) . . ?
C15 N11 C16 124.4(13) . . ?
C14 N13 C12 109.4(13) . . ?
C14 N13 C19 124.1(13) . . ?
C12 N13 C19 126.4(13) . . ?
F4 P F1 89.2(7) . . ?
F4 P F3 90.1(6) . . ?
F1 P F3 178.7(6) . . ?
F4 P F5 90.6(6) . . ?
F1 P F5 89.0(6) . . ?
F3 P F5 89.9(5) . . ?
F4 P F6 89.6(6) . . ?
F1 P F6 90.9(6) . . ?
F3 P F6 90.2(6) . . ?
F5 P F6 179.7(7) . . ?
F4 P F2 178.8(6) . . ?
F1 P F2 90.3(7) . . ?
F3 P F2 90.4(6) . . ?
F5 P F2 90.5(6) . . ?
F6 P F2 89.2(6) . . ?

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
N3 C4 C5 N1 -0.6(18) . . . . ?
N1 C6 C7 C8 -75.2(18) . . . . ?
C6 C7 C8 C18 172.8(14) . . . . ?
N13 C14 C15 N11 0.3(17) . . . . ?
N11 C16 C17 C18 59.8(19) . . . . ?
C16 C17 C18 C8 175.0(14) . . . . ?
C7 C8 C18 C17 175.5(14) . . . . ?
N1 C2 Au C12 -129(12) . . . 2_565 ?
N3 C2 Au C12 44(13) . . . 2_565 ?
N1 C2 Au Au 79.2(13) . . . 2_575 ?
N3 C2 Au Au -108.3(11) . . . 2_575 ?
N3 C2 N1 C5 0.9(16) . . . . ?
Au C2 N1 C5 174.3(11) . . . . ?
N3 C2 N1 C6 178.9(13) . . . . ?
Au C2 N1 C6 -8(2) . . . . ?
C4 C5 N1 C2 -0.1(18) . . . . ?
C4 C5 N1 C6 -178.3(14) . . . . ?
C7 C6 N1 C2 105.8(18) . . . . ?
C7 C6 N1 C5 -76.3(19) . . . . ?
N1 C2 N3 C4 -1.3(16) . . . . ?
Au C2 N3 C4 -175.1(11) . . . . ?
N1 C2 N3 C9 177.0(13) . . . . ?
Au C2 N3 C9 3(2) . . . . ?
C5 C4 N3 C2 1.2(18) . . . . ?
C5 C4 N3 C9 -177.0(15) . . . . ?
C10 C9 N3 C2 -82.3(19) . . . . ?
C10 C9 N3 C4 95.7(19) . . . . ?
N13 C12 N11 C15 0.2(16) . . . . ?
Au C12 N11 C15 -177.2(10) 2_565 . . . ?
N13 C12 N11 C16 -174.9(13) . . . . ?
Au C12 N11 C16 8(2) 2_565 . . . ?
C14 C15 N11 C12 -0.3(17) . . . . ?
C14 C15 N11 C16 174.9(14) . . . . ?
C17 C16 N11 C12 83.7(18) . . . . ?
C17 C16 N11 C15 -90.6(18) . . . . ?
C15 C14 N13 C12 -0.2(17) . . . . ?
C15 C14 N13 C19 -176.5(14) . . . . ?
N11 C12 N13 C14 0.0(16) . . . . ?
Au C12 N13 C14 177.6(10) 2_565 . . . ?
N11 C12 N13 C19 176.2(14) . . . . ?
Au C12 N13 C19 -6(2) 2_565 . . . ?
C20 C19 N13 C14 83.3(19) . . . . ?
C20 C19 N13 C12 -92.3(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         5.040
_refine_diff_density_min         -2.022
_refine_diff_density_rms         0.319
#END---------------------------------------------------------------------------
