# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Audibipy
_database_code_depnum_ccdc_archive 'CCDC 1449961'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Au2 Cl6 N2'
_chemical_formula_weight         762.82

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'

_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                   16.2461(6)
_cell_length_b                   7.5152(3)
_cell_length_c                   14.1846(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.938(3)
_cell_angle_gamma                90
_cell_volume                     1715.24(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    6623
_cell_measurement_theta_min      2.9860
_cell_measurement_theta_max      28.0590

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.954
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    18.010
_shelx_estimated_absorpt_T_min   0.266
_shelx_estimated_absorpt_T_max   0.715
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.177
_exptl_absorpt_correction_T_max  0.574
_exptl_absorpt_process_details   
;   
CrysAlisPro (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897,
Agilent Technologies, 2014)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12813
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.900
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1517
_reflns_number_gt                1419
_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       
;
CrysAlisPro, Agilent Technologies (2014)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies (2014)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies (2014)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Bruno, et al. 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0212P)²+9.4752P] 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         1517
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0194
_refine_ls_wR_factor_ref         0.0487
_refine_ls_wR_factor_gt          0.0478
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.197
_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_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
C1 C 0.1168(3) -0.1006(8) 0.1141(4) 0.0216(12) Uani 1 1 d . . . . .
H1 H 0.1270 -0.1978 0.0744 0.026 Uiso 1 1 calc R U . . .
C2 C 0.0493(3) -0.1052(8) 0.1626(4) 0.0237(12) Uani 1 1 d . . . . .
H2 H 0.0129 -0.2047 0.1566 0.028 Uiso 1 1 calc R U . . .
C3 C 0.0345(3) 0.0381(7) 0.2211(4) 0.0192(12) Uani 1 1 d . . . . .
C4 C 0.0865(3) 0.1850(8) 0.2228(4) 0.0222(12) Uani 1 1 d . . . . .
H4 H 0.0758 0.2874 0.2584 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1531(3) 0.1829(8) 0.1735(4) 0.0234(12) Uani 1 1 d . . . . .
H5 H 0.1887 0.2836 0.1758 0.028 Uiso 1 1 calc R U . . .
N1 N 0.1688(3) 0.0403(6) 0.1220(3) 0.0212(10) Uani 1 1 d . . . . .
Cl1 Cl 0.20720(9) -0.0438(2) -0.08004(10) 0.0285(3) Uani 1 1 d . . . . .
Cl2 Cl 0.39982(9) 0.0244(2) 0.00574(12) 0.0315(3) Uani 1 1 d . . . . .
Cl3 Cl 0.34637(9) 0.1056(2) 0.20927(10) 0.0291(3) Uani 1 1 d . . . . .
Au1 Au 0.27739(2) 0.03082(3) 0.06456(2) 0.01927(9) 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
C1 0.024(3) 0.017(3) 0.024(3) -0.003(2) 0.004(2) 0.000(2)
C2 0.030(3) 0.019(3) 0.025(3) 0.004(2) 0.011(2) -0.002(2)
C3 0.021(3) 0.018(3) 0.019(3) 0.003(2) 0.005(2) 0.000(2)
C4 0.022(3) 0.022(3) 0.023(3) -0.003(2) 0.007(2) -0.001(2)
C5 0.027(3) 0.016(3) 0.028(3) -0.001(2) 0.007(2) -0.001(2)
N1 0.027(3) 0.016(3) 0.022(2) 0.0007(19) 0.009(2) 0.002(2)
Cl1 0.0319(8) 0.0327(9) 0.0217(7) -0.0011(6) 0.0069(6) -0.0023(6)
Cl2 0.0244(7) 0.0301(9) 0.0436(9) -0.0058(7) 0.0176(7) -0.0014(6)
Cl3 0.0316(7) 0.0260(8) 0.0289(7) -0.0027(6) 0.0014(6) 0.0001(6)
Au1 0.02050(13) 0.01671(14) 0.02228(13) 0.00040(8) 0.00890(9) 0.00066(8)

_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
C1 N1 1.350(7) . ?
C1 C2 1.375(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.400(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(8) . ?
C3 C3 1.477(10) 2 ?
C4 C5 1.367(8) . ?
C4 H4 0.9500 . ?
C5 N1 1.342(7) . ?
C5 H5 0.9500 . ?
N1 Au1 2.043(4) . ?
Cl1 Au1 2.2751(15) . ?
Cl2 Au1 2.2613(14) . ?
Cl3 Au1 2.2692(14) . ?

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 C1 C2 120.8(5) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 119.5(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 117.9(5) . . ?
C4 C3 C3 119.8(4) . 2 ?
C2 C3 C3 122.3(4) . 2 ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 120.8(5) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 N1 C1 120.5(5) . . ?
C5 N1 Au1 119.0(4) . . ?
C1 N1 Au1 120.3(4) . . ?
N1 Au1 Cl2 178.02(14) . . ?
N1 Au1 Cl3 88.65(14) . . ?
Cl2 Au1 Cl3 89.39(6) . . ?
N1 Au1 Cl1 90.87(14) . . ?
Cl2 Au1 Cl1 91.09(6) . . ?
Cl3 Au1 Cl1 179.52(5) . . ?

_refine_diff_density_max         1.023
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.139

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7

TITL SIR2004 run in space group C 2/c
CELL  0.71073  16.2461   7.5152  14.1846   90.000   97.938   90.000
ZERR     4.00   0.0006   0.0003   0.0005    0.000    0.003    0.000
LATT   7
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    N    CL   AU
UNIT  40 32 8 24 8
MERG   2
OMIT   -10   0   2
FMAP   2
PLAN   25
SIZE     0.020   0.100   0.100
ACTA
BOND   $H
L.S.  20
TEMP  -143.00
WGHT    0.021200    9.475200
FVAR       0.90783
C1    1    0.116831   -0.100636    0.114051    11.00000    0.02439    0.01685 =
         0.02361   -0.00289    0.00393    0.00041
AFIX  43
H1    2    0.127027   -0.197827    0.074431    11.00000   -1.20000
AFIX   0
C2    1    0.049261   -0.105153    0.162646    11.00000    0.02964    0.01879 =
         0.02472    0.00397    0.01131   -0.00183
AFIX  43
H2    2    0.012897   -0.204741    0.156615    11.00000   -1.20000
AFIX   0
C3    1    0.034472    0.038126    0.221070    11.00000    0.02075    0.01838 =
         0.01892    0.00313    0.00472    0.00044
C4    1    0.086492    0.184998    0.222829    11.00000    0.02227    0.02203 =
         0.02321   -0.00350    0.00666   -0.00080
AFIX  43
H4    2    0.075755    0.287429    0.258440    11.00000   -1.20000
AFIX   0
C5    1    0.153116    0.182883    0.173532    11.00000    0.02676    0.01622 =
         0.02801   -0.00071    0.00668   -0.00058
AFIX  43
H5    2    0.188687    0.283576    0.175809    11.00000   -1.20000
AFIX   0
N1    3    0.168843    0.040253    0.121976    11.00000    0.02744    0.01608 =
         0.02157    0.00069    0.00874    0.00168
CL1   4    0.207197   -0.043821   -0.080037    11.00000    0.03187    0.03273 =
         0.02167   -0.00110    0.00694   -0.00231
CL2   4    0.399820    0.024408    0.005741    11.00000    0.02437    0.03007 =
         0.04364   -0.00584    0.01756   -0.00136
CL3   4    0.346369    0.105563    0.209272    11.00000    0.03156    0.02602 =
         0.02888   -0.00270    0.00140    0.00008
AU1   5    0.277386    0.030824    0.064563    11.00000    0.02050    0.01671 =
         0.02228    0.00040    0.00890    0.00066
HKLF    4

REM  SIR2004 run in space group C 2/c
REM R1 =  0.0194 for    1419 Fo > 4sig(Fo)  and  0.0221 for all    1517 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0212      9.4752

REM Highest difference peak  1.023,  deepest hole -0.450,  1-sigma level  0.139
Q1    1   0.2215  0.0167  0.0367  11.00000  0.05    1.02
Q2    1   0.3093 -0.0144  0.1228  11.00000  0.05    0.90
Q3    1   0.3001  0.0212  0.1374  11.00000  0.05    0.85
Q4    1   0.1387  0.1217 -0.0735  11.00000  0.05    0.79
Q5    1   0.1427 -0.1536 -0.0737  11.00000  0.05    0.77
Q6    1   0.4025  0.1164  0.1764  11.00000  0.05    0.72
Q7    1   0.1031  0.3833  0.3206  11.00000  0.05    0.66
Q8    1  -0.0220 -0.2616  0.1960  11.00000  0.05    0.65
Q9    1   0.0179  0.2703  0.3033  11.00000  0.05    0.58
Q10   1   0.2733 -0.1060  0.0601  11.00000  0.05    0.46
Q11   1   0.2682  0.0324 -0.0234  11.00000  0.05    0.45
Q12   1  -0.0399 -0.2188  0.1030  11.00000  0.05    0.44
Q13   1   0.4214 -0.0268  0.0550  11.00000  0.05    0.42
Q14   1   0.3403 -0.1162 -0.0375  11.00000  0.05    0.40
Q15   1   0.4022  0.1295  0.0497  11.00000  0.05    0.38
Q16   1   0.3947  0.0328  0.2413  11.00000  0.05    0.38
Q17   1   0.1374  0.2572  0.0777  11.00000  0.05    0.36
Q18   1   0.2107 -0.0229 -0.1464  11.00000  0.05    0.36
Q19   1   0.1455  0.1370  0.1249  11.00000  0.05    0.35
Q20   1   0.1683  0.0135 -0.0280  11.00000  0.05    0.34
Q21   1   0.2406  0.0459  0.2137  11.00000  0.05    0.34
Q22   1   0.1130  0.0509  0.0626  11.00000  0.05    0.33
Q23   1  -0.0016 -0.2503 -0.0227  11.00000  0.05    0.33
Q24   1   0.0557  0.1919  0.4024  11.00000  0.05    0.33
Q25   1   0.0229  0.0083  0.1833  11.00000  0.05    0.32
;
_shelx_res_checksum              18510
