# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1502277'
_audit_update_record             
;
2016-09-02 deposited with the CCDC.
2018-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 Au Cl4 N2'
_chemical_formula_weight         512.00

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   21.246(4)
_cell_length_b                   6.9996(14)
_cell_length_c                   10.658(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1585.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5505
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      25.02

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    9.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1673
_exptl_absorpt_correction_T_max  0.1989
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5505
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1527
_reflns_number_gt                1194
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0173P)²+4.1154P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1527
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_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 0.14227(2) 0.2500 0.57596(5) 0.05137(18) Uani 1 2 d S . .
Cl1 Cl 0.18362(19) 0.2500 0.7724(4) 0.0877(12) Uani 1 2 d S . .
Cl2 Cl 0.04330(17) 0.2500 0.6561(4) 0.0817(12) Uani 1 2 d S . .
Cl3 Cl 0.1015(2) 0.2500 0.3799(4) 0.0940(13) Uani 1 2 d S . .
Cl4 Cl 0.24105(19) 0.2500 0.4972(4) 0.1044(15) Uani 1 2 d S . .
N1 N 0.2996(5) 0.2500 0.1208(11) 0.059(3) Uani 1 2 d S . .
N2 N 0.3942(5) 0.2500 0.1901(11) 0.056(3) Uani 1 2 d S . .
C1 C 0.2307(6) 0.2500 0.1183(15) 0.095(5) Uani 1 2 d S . .
H1A H 0.2149 0.3086 0.1934 0.143 Uiso 0.50 1 calc PR . .
H1B H 0.2157 0.1209 0.1132 0.143 Uiso 0.50 1 calc PR . .
H1C H 0.2163 0.3205 0.0465 0.143 Uiso 0.50 1 calc PR . .
C2 C 0.3377(7) 0.2500 0.0181(15) 0.071(4) Uani 1 2 d S . .
H2 H 0.3250 0.2500 -0.0653 0.085 Uiso 1 2 calc SR . .
C3 C 0.3971(7) 0.2500 0.0603(13) 0.061(4) Uani 1 2 d S . .
H3 H 0.4335 0.2500 0.0117 0.073 Uiso 1 2 calc SR . .
C4 C 0.3337(6) 0.2500 0.2238(14) 0.061(4) Uani 1 2 d S . .
H4 H 0.3183 0.2500 0.3055 0.073 Uiso 1 2 calc SR . .
C5 C 0.4492(6) 0.2500 0.2723(15) 0.075(4) Uani 1 2 d S . .
H5A H 0.4745 0.3620 0.2544 0.090 Uiso 0.50 1 calc PR . .
H5B H 0.4745 0.1380 0.2544 0.090 Uiso 0.50 1 calc PR . .
C6 C 0.4317(6) 0.2500 0.4099(14) 0.068(4) Uani 1 2 d S . .
C7 C 0.4247(5) 0.0791(17) 0.4738(12) 0.088(3) Uani 1 1 d . . .
H7 H 0.4292 -0.0371 0.4324 0.106 Uiso 1 1 calc R . .
C8 C 0.4111(6) 0.085(3) 0.5972(13) 0.131(7) Uani 1 1 d . . .
H8 H 0.4068 -0.0302 0.6399 0.157 Uiso 1 1 calc R . .
C9 C 0.4032(11) 0.2500 0.663(2) 0.172(19) Uani 1 2 d S . .
H9 H 0.3931 0.2500 0.7475 0.206 Uiso 1 2 calc 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 0.0539(3) 0.0605(3) 0.0397(3) 0.000 -0.0008(3) 0.000
Cl1 0.091(3) 0.126(3) 0.046(2) 0.000 -0.016(2) 0.000
Cl2 0.061(2) 0.099(3) 0.085(3) 0.000 0.012(2) 0.000
Cl3 0.111(3) 0.123(3) 0.048(2) 0.000 -0.021(3) 0.000
Cl4 0.062(3) 0.173(4) 0.078(3) 0.000 0.022(2) 0.000
N1 0.052(7) 0.083(7) 0.041(7) 0.000 0.009(6) 0.000
N2 0.052(7) 0.065(6) 0.050(8) 0.000 0.017(6) 0.000
C1 0.051(9) 0.166(15) 0.069(12) 0.000 -0.010(9) 0.000
C2 0.082(11) 0.081(10) 0.049(9) 0.000 0.021(9) 0.000
C3 0.059(9) 0.080(9) 0.044(10) 0.000 0.022(8) 0.000
C4 0.057(8) 0.082(9) 0.044(9) 0.000 0.002(8) 0.000
C5 0.031(7) 0.119(11) 0.073(11) 0.000 -0.003(8) 0.000
C6 0.039(7) 0.111(11) 0.053(10) 0.000 -0.008(8) 0.000
C7 0.067(7) 0.116(9) 0.081(9) 0.023(8) -0.019(7) -0.006(6)
C8 0.059(9) 0.25(2) 0.081(13) 0.087(14) -0.020(9) -0.019(11)
C9 0.055(13) 0.41(6) 0.047(16) 0.000 0.003(12) 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 Cl4 2.260(4) . ?
Au1 Cl3 2.262(4) . ?
Au1 Cl1 2.271(4) . ?
Au1 Cl2 2.270(4) . ?
N1 C4 1.314(15) . ?
N1 C2 1.361(16) . ?
N1 C1 1.466(15) . ?
N2 C4 1.336(14) . ?
N2 C3 1.384(16) . ?
N2 C5 1.460(16) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.340(18) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.513(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.384(13) 8_565 ?
C6 C7 1.384(13) . ?
C7 C8 1.347(16) . ?
C7 H7 0.9300 . ?
C8 C9 1.360(18) . ?
C8 H8 0.9300 . ?
C9 C8 1.360(18) 8_565 ?
C9 H9 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
Cl4 Au1 Cl3 90.73(17) . . ?
Cl4 Au1 Cl1 89.03(16) . . ?
Cl3 Au1 Cl1 179.76(16) . . ?
Cl4 Au1 Cl2 179.69(17) . . ?
Cl3 Au1 Cl2 89.59(16) . . ?
Cl1 Au1 Cl2 90.66(16) . . ?
C4 N1 C2 110.1(11) . . ?
C4 N1 C1 124.4(12) . . ?
C2 N1 C1 125.4(13) . . ?
C4 N2 C3 108.2(12) . . ?
C4 N2 C5 127.5(12) . . ?
C3 N2 C5 124.3(11) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 106.9(14) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 N2 107.0(12) . . ?
C2 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
N1 C4 N2 107.8(12) . . ?
N1 C4 H4 126.1 . . ?
N2 C4 H4 126.1 . . ?
N2 C5 C6 112.7(10) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C7 119.5(16) 8_565 . ?
C7 C6 C5 120.2(8) 8_565 . ?
C7 C6 C5 120.2(8) . . ?
C8 C7 C6 118.5(15) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C7 C8 C9 124(2) . . ?
C7 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
C8 C9 C8 116(2) 8_565 . ?
C8 C9 H9 121.8 8_565 . ?
C8 C9 H9 121.8 . . ?

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
C4 N1 C2 C3 0.0 . . . . ?
C1 N1 C2 C3 180.0 . . . . ?
N1 C2 C3 N2 0.0 . . . . ?
C4 N2 C3 C2 0.0 . . . . ?
C5 N2 C3 C2 180.0 . . . . ?
C2 N1 C4 N2 0.0 . . . . ?
C1 N1 C4 N2 180.0 . . . . ?
C3 N2 C4 N1 0.0 . . . . ?
C5 N2 C4 N1 180.0 . . . . ?
C4 N2 C5 C6 0.000(1) . . . . ?
C3 N2 C5 C6 180.000(1) . . . . ?
N2 C5 C6 C7 -91.1(11) . . . 8_565 ?
N2 C5 C6 C7 91.1(11) . . . . ?
C7 C6 C7 C8 0(2) 8_565 . . . ?
C5 C6 C7 C8 177.9(11) . . . . ?
C6 C7 C8 C9 1(3) . . . . ?
C7 C8 C9 C8 -1(4) . . . 8_565 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.140
_refine_diff_density_min         -1.133
_refine_diff_density_rms         0.149
