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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1
_audit_creation_date             2013-12-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H10 Au Br2 N, H2 O'
_chemical_formula_sum            'C12 H12 Au Br2 N O'
_chemical_formula_weight         543.01
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2br2au1
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0801(4)
_cell_length_b                   10.0993(7)
_cell_length_c                   10.1771(7)
_cell_angle_alpha                97.689(5)
_cell_angle_beta                 99.690(5)
_cell_angle_gamma                92.960(5)
_cell_volume                     708.83(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2944
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6530
_cell_measurement_theta_min      3.6780
_shelx_estimated_absorpt_T_max   0.502
_shelx_estimated_absorpt_T_min   0.086
_exptl_absorpt_coefficient_mu    15.998
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5824
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.927
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0055245000
_diffrn_orient_matrix_UB_12      -0.0254678000
_diffrn_orient_matrix_UB_13      0.0610117000
_diffrn_orient_matrix_UB_21      0.0531774000
_diffrn_orient_matrix_UB_22      -0.0543723000
_diffrn_orient_matrix_UB_23      -0.0202895000
_diffrn_orient_matrix_UB_31      0.0867787000
_diffrn_orient_matrix_UB_32      0.0380350000
_diffrn_orient_matrix_UB_33      0.0311766000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2596
_reflns_number_total             2890
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2012 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         6.486
_refine_diff_density_min         -1.947
_refine_diff_density_rms         0.442
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0658
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1469P)²+0.4645P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1853
_refine_ls_wR_factor_ref         0.1941
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.26926(6) 0.36887(4) 0.11295(4) 0.0363(2) Uani 1 1 d . . . . .
Br1 Br 0.3221(3) 0.30020(19) 0.34287(16) 0.0625(5) Uani 1 1 d . . . . .
Br2 Br 0.2239(3) 0.13548(15) 0.02120(19) 0.0631(5) Uani 1 1 d . . . . .
C1 C 0.342(2) 0.6246(15) 0.3050(13) 0.052(3) Uani 1 1 d . . . . .
H1 H 0.3625 0.5674 0.3695 0.062 Uiso 1 1 calc R . . . .
C2 C 0.355(3) 0.7560(16) 0.3479(16) 0.065(4) Uani 1 1 d . . . . .
H2 H 0.3785 0.7905 0.4390 0.078 Uiso 1 1 calc R . . . .
C3 C 0.330(3) 0.8386(19) 0.2477(19) 0.083(6) Uani 1 1 d . . . . .
H3 H 0.3377 0.9310 0.2727 0.099 Uiso 1 1 calc R . . . .
C4 C 0.294(3) 0.7865(16) 0.1120(15) 0.058(4) Uani 1 1 d . . . . .
H4 H 0.2805 0.8430 0.0465 0.070 Uiso 1 1 calc R . . . .
C5 C 0.2786(18) 0.6499(14) 0.0760(12) 0.039(3) Uani 1 1 d . . . . .
C6 C 0.2374(17) 0.5771(17) -0.0653(14) 0.049(4) Uani 1 1 d . . . . .
C7 C 0.2274(17) 0.4361(14) -0.0706(13) 0.038(3) Uani 1 1 d . . . . .
C8 C 0.191(2) 0.3514(15) -0.1925(13) 0.048(3) Uani 1 1 d . . . . .
H8 H 0.1816 0.2587 -0.1958 0.058 Uiso 1 1 calc R . . . .
C9 C 0.168(2) 0.4103(17) -0.3099(14) 0.058(4) Uani 1 1 d . . . . .
H9 H 0.1458 0.3564 -0.3934 0.070 Uiso 1 1 calc R . . . .
C10 C 0.179(2) 0.5450(16) -0.3033(13) 0.049(3) Uani 1 1 d . . . . .
H10 H 0.1625 0.5833 -0.3823 0.059 Uiso 1 1 calc R . . . .
C11 C 0.2163(16) 0.6277(13) -0.1777(17) 0.046(3) Uani 1 1 d . . . . .
C12 C 0.224(2) 0.7755(16) -0.1933(17) 0.058(4) Uani 1 1 d . . . . .
H12A H 0.1226 0.8169 -0.1554 0.087 Uiso 1 1 calc GR . . . .
H12B H 0.2087 0.7843 -0.2872 0.087 Uiso 1 1 calc GR . . . .
H12C H 0.3458 0.8184 -0.1473 0.087 Uiso 1 1 calc GR . . . .
N1 N 0.3014(15) 0.5702(11) 0.1774(10) 0.038(2) Uani 1 1 d . . . . .
O1 O 0.7964(12) 0.9661(7) 0.4277(8) 0.0390(18) Uani 1 1 d . . . . .
H1A H 0.8568 0.9036 0.4597 0.058 Uiso 1 1 d G . . . .
H1B H 0.8574 1.0412 0.4602 0.058 Uiso 1 1 d G . . . .


_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 Br1 2.5024(15) . ?
Au1 Br2 2.4005(16) . ?
Au1 C7 2.052(13) . ?
Au1 N1 2.040(11) . ?
C1 H1 0.9300 . ?
C1 C2 1.33(2) . ?
C1 N1 1.317(16) . ?
C2 H2 0.9300 . ?
C2 C3 1.40(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.39(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.37(2) . ?
C5 C6 1.499(16) . ?
C5 N1 1.386(17) . ?
C6 C7 1.42(2) . ?
C6 C11 1.30(2) . ?
C7 C8 1.387(18) . ?
C8 H8 0.9300 . ?
C8 C9 1.39(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.35(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.41(2) . ?
C11 C12 1.521(18) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O1 H1A 0.8499 . ?
O1 H1B 0.8502 . ?

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
Br2 Au1 Br1 88.09(6) . . ?
C7 Au1 Br1 176.8(4) . . ?
C7 Au1 Br2 95.1(4) . . ?
N1 Au1 Br1 95.9(3) . . ?
N1 Au1 Br2 175.9(3) . . ?
N1 Au1 C7 80.9(5) . . ?
C2 C1 H1 117.7 . . ?
N1 C1 H1 117.7 . . ?
N1 C1 C2 124.6(14) . . ?
C1 C2 H2 122.0 . . ?
C1 C2 C3 116.0(14) . . ?
C3 C2 H2 122.0 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.7(16) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(15) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 125.7(13) . . ?
C4 C5 N1 118.3(11) . . ?
N1 C5 C6 116.0(12) . . ?
C7 C6 C5 112.8(13) . . ?
C11 C6 C5 128.2(14) . . ?
C11 C6 C7 119.0(12) . . ?
C6 C7 Au1 115.3(9) . . ?
C8 C7 Au1 123.3(11) . . ?
C8 C7 C6 121.3(13) . . ?
C7 C8 H8 121.3 . . ?
C7 C8 C9 117.5(14) . . ?
C9 C8 H8 121.3 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.5(12) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(12) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 C10 121.3(12) . . ?
C6 C11 C12 127.0(15) . . ?
C10 C11 C12 111.8(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 Au1 124.3(10) . . ?
C1 N1 C5 120.6(12) . . ?
C5 N1 Au1 115.1(8) . . ?
H1A O1 H1B 109.4 . . ?

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
Au1 C7 C8 C9 -178.9(11) . . . . ?
C1 C2 C3 C4 0(3) . . . . ?
C2 C1 N1 Au1 -176.9(13) . . . . ?
C2 C1 N1 C5 3(2) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C3 C4 C5 C6 179.0(15) . . . . ?
C3 C4 C5 N1 -1(2) . . . . ?
C4 C5 C6 C7 -179.1(14) . . . . ?
C4 C5 C6 C11 3(2) . . . . ?
C4 C5 N1 Au1 178.6(11) . . . . ?
C4 C5 N1 C1 -2(2) . . . . ?
C5 C6 C7 Au1 0.4(13) . . . . ?
C5 C6 C7 C8 -179.9(11) . . . . ?
C5 C6 C11 C10 179.5(11) . . . . ?
C5 C6 C11 C12 -1(2) . . . . ?
C6 C5 N1 Au1 -1.0(14) . . . . ?
C6 C5 N1 C1 178.7(11) . . . . ?
C6 C7 C8 C9 1(2) . . . . ?
C7 C6 C11 C10 2(2) . . . . ?
C7 C6 C11 C12 -179.4(11) . . . . ?
C7 C8 C9 C10 -1(2) . . . . ?
C8 C9 C10 C11 1(2) . . . . ?
C9 C10 C11 C6 -1(2) . . . . ?
C9 C10 C11 C12 179.6(14) . . . . ?
C11 C6 C7 Au1 178.6(10) . . . . ?
C11 C6 C7 C8 -1.7(19) . . . . ?
N1 C1 C2 C3 -2(3) . . . . ?
N1 C5 C6 C7 0.4(16) . . . . ?
N1 C5 C6 C11 -177.6(13) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1000469'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wq-01-gxt-01
_audit_creation_date             2014-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H15 Au Br N'
_chemical_formula_sum            'C18 H15 Au Br N'
_chemical_formula_weight         522.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.4197 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.9554(3)
_cell_length_b                   11.7205(2)
_cell_length_c                   16.8390(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3148.98(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6677
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.4940
_cell_measurement_theta_min      5.2370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    20.451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14523
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         5.370
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0364249000
_diffrn_orient_matrix_UB_12      0.0010408000
_diffrn_orient_matrix_UB_13      -0.0847062000
_diffrn_orient_matrix_UB_21      0.0893957000
_diffrn_orient_matrix_UB_22      -0.0026645000
_diffrn_orient_matrix_UB_23      -0.0345340000
_diffrn_orient_matrix_UB_31      -0.0021077000
_diffrn_orient_matrix_UB_32      -0.1314279000
_diffrn_orient_matrix_UB_33      0.0000338000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2562
_reflns_number_total             2812
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         4.382
_refine_diff_density_min         -4.688
_refine_diff_density_rms         0.556
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1302P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1723
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.5552(5) 0.3529(6) 0.4703(4) 0.0175(14) Uani 1 1 d . . . . .
H1 H 0.5321 0.3230 0.5166 0.021 Uiso 1 1 calc R . . . .
C2 C 0.6396(5) 0.3406(7) 0.4580(5) 0.0194(16) Uani 1 1 d . . . . .
H2 H 0.6738 0.3059 0.4956 0.023 Uiso 1 1 calc R . . . .
C3 C 0.6722(6) 0.3822(7) 0.3870(5) 0.0217(18) Uani 1 1 d . . . . .
H3 H 0.7284 0.3708 0.3745 0.026 Uiso 1 1 calc R . . . .
C4 C 0.6200(5) 0.4412(8) 0.3344(5) 0.0218(18) Uani 1 1 d . . . . .
H4 H 0.6417 0.4714 0.2876 0.026 Uiso 1 1 calc R . . . .
C5 C 0.4931(5) 0.5834(6) 0.2375(4) 0.0205(17) Uani 1 1 d . . . . .
C6 C 0.4282(7) 0.6176(7) 0.1867(5) 0.029(2) Uani 1 1 d . . . . .
H6 H 0.4404 0.6645 0.1437 0.035 Uiso 1 1 calc R . . . .
C7 C 0.3464(8) 0.5830(9) 0.1991(7) 0.040(2) Uani 1 1 d . . . . .
H7 H 0.3050 0.6019 0.1625 0.048 Uiso 1 1 calc R . . . .
C8 C 0.3264(6) 0.5203(7) 0.2659(5) 0.0253(17) Uani 1 1 d . . . . .
H8 H 0.2707 0.5023 0.2765 0.030 Uiso 1 1 calc R . . . .
C9 C 0.3893(5) 0.4839(6) 0.3175(4) 0.0141(14) Uani 1 1 d . . . . .
C10 C 0.4737(5) 0.5098(5) 0.3015(4) 0.0141(13) Uiso 1 1 d . . . . .
C11 C 0.5364(4) 0.4544(5) 0.3521(4) 0.0115(13) Uani 1 1 d . . . . .
C12 C 0.2455(7) 0.3918(6) 0.4090(5) 0.0191(19) Uiso 1 1 d . . . . .
C13 C 0.2069(6) 0.3143(7) 0.3610(5) 0.0277(17) Uani 1 1 d . . . . .
H13 H 0.2391 0.2646 0.3306 0.033 Uiso 1 1 calc R . . . .
C14 C 0.1206(5) 0.3086(8) 0.3569(5) 0.030(2) Uani 1 1 d . . . . .
H14 H 0.0950 0.2547 0.3245 0.036 Uiso 1 1 calc R . . . .
C15 C 0.0721(7) 0.3831(9) 0.4011(7) 0.034(2) Uani 1 1 d . . . . .
H15 H 0.0139 0.3799 0.3983 0.041 Uiso 1 1 calc R . . . .
C16 C 0.1106(7) 0.4618(10) 0.4492(7) 0.040(2) Uani 1 1 d . . . . .
H16 H 0.0785 0.5130 0.4785 0.048 Uiso 1 1 calc R . . . .
C17 C 0.1958(5) 0.4650(8) 0.4542(5) 0.0291(18) Uani 1 1 d . . . . .
H17 H 0.2212 0.5168 0.4884 0.035 Uiso 1 1 calc R . . . .
C18 C 0.5785(6) 0.6365(8) 0.2234(5) 0.0308(18) Uani 1 1 d . . . . .
H18A H 0.6066 0.6465 0.2733 0.046 Uiso 1 1 calc GR . . . .
H18B H 0.5717 0.7092 0.1981 0.046 Uiso 1 1 calc GR . . . .
H18C H 0.6111 0.5873 0.1900 0.046 Uiso 1 1 calc GR . . . .
N1 N 0.5045(6) 0.4055(4) 0.4192(3) 0.0119(16) Uiso 1 1 d . . . . .
Br1 Br 0.36012(6) 0.28897(8) 0.54661(5) 0.0283(3) Uani 1 1 d . . . . .
Au1 Au 0.37191(2) 0.39728(2) 0.41997(2) 0.0107(2) 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
C1 C2 1.371(11) . ?
C1 N1 1.332(10) . ?
C2 C3 1.392(12) . ?
C3 C4 1.399(12) . ?
C4 C11 1.375(10) . ?
C5 C6 1.402(12) . ?
C5 C10 1.414(9) . ?
C5 C18 1.516(12) . ?
C6 C7 1.381(17) . ?
C7 C8 1.381(14) . ?
C8 C9 1.394(11) . ?
C9 C10 1.407(10) . ?
C9 Au1 2.022(7) . ?
C10 C11 1.465(9) . ?
C11 N1 1.366(9) . ?
C12 C13 1.363(12) . ?
C12 C17 1.396(11) . ?
C12 Au1 2.026(11) . ?
C13 C14 1.381(12) . ?
C14 C15 1.384(16) . ?
C15 C16 1.373(16) . ?
C16 C17 1.362(13) . ?
N1 Au1 2.117(9) . ?
Br1 Au1 2.4889(9) . ?

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 123.2(7) . . ?
C1 C2 C3 117.4(7) . . ?
C2 C3 C4 119.6(8) . . ?
C11 C4 C3 119.8(8) . . ?
C6 C5 C10 118.5(8) . . ?
C6 C5 C18 116.8(7) . . ?
C10 C5 C18 124.5(7) . . ?
C7 C6 C5 121.4(8) . . ?
C6 C7 C8 119.9(9) . . ?
C7 C8 C9 120.2(9) . . ?
C8 C9 C10 120.3(7) . . ?
C8 C9 Au1 125.9(6) . . ?
C10 C9 Au1 113.8(5) . . ?
C5 C10 C11 124.3(7) . . ?
C9 C10 C5 119.1(7) . . ?
C9 C10 C11 116.5(6) . . ?
C4 C11 C10 125.9(6) . . ?
N1 C11 C4 119.6(7) . . ?
N1 C11 C10 114.4(6) . . ?
C13 C12 C17 118.4(9) . . ?
C13 C12 Au1 121.7(7) . . ?
C17 C12 Au1 119.8(7) . . ?
C12 C13 C14 120.8(9) . . ?
C13 C14 C15 120.1(8) . . ?
C16 C15 C14 119.4(10) . . ?
C17 C16 C15 120.1(10) . . ?
C16 C17 C12 121.1(9) . . ?
C1 N1 C11 120.2(8) . . ?
C1 N1 Au1 125.6(5) . . ?
C11 N1 Au1 113.4(5) . . ?
C9 Au1 C12 94.3(3) . . ?
C9 Au1 N1 80.5(3) . . ?
C9 Au1 Br1 176.4(2) . . ?
C12 Au1 N1 174.4(3) . . ?
C12 Au1 Br1 89.3(2) . . ?
N1 Au1 Br1 95.96(16) . . ?

_database_code_depnum_ccdc_archive 'CCDC 1007212'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wq6
_audit_creation_date             2014-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 Au Cl2 N'
_chemical_formula_sum            'C18 H16 Au Cl2 N'
_chemical_formula_weight         514.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.4197 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8572(3)
_cell_length_b                   8.2744(4)
_cell_length_c                   15.3789(5)
_cell_angle_alpha                93.413(3)
_cell_angle_beta                 103.381(3)
_cell_angle_gamma                113.776(4)
_cell_volume                     876.94(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8880
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.6200
_cell_measurement_theta_min      5.8800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    18.515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'yellowish yellow'
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15399
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         5.932
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -77.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -38.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000 -120.0000 67

#__ type_ start__ end____ width___ exp.time_
  6 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -19.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   91.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00  116.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00  109.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   91.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega  100.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
 14 omega   37.00  146.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 109

#__ type_ start__ end____ width___ exp.time_
 15 omega   91.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
 16 omega   57.00  150.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 93

#__ type_ start__ end____ width___ exp.time_
 17 omega   40.00   98.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00   91.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 19 omega   39.00  109.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00   91.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
 21 omega  100.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
 22 omega   38.00   91.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 23 omega   41.00  126.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
 24 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000 -180.0000 67

#__ type_ start__ end____ width___ exp.time_
 25 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
 26 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
 27 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -38.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
 28 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
 29 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
 30 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
 31 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
 32 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 95

#__ type_ start__ end____ width___ exp.time_
 33 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
 34 omega   70.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 108

#__ type_ start__ end____ width___ exp.time_
 35 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
 36 omega   70.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 108

#__ type_ start__ end____ width___ exp.time_
 37 omega   91.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
 38 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
 39 omega   87.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

#__ type_ start__ end____ width___ exp.time_
 40 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
 41 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
 42 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
 43 omega   81.00  176.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

#__ type_ start__ end____ width___ exp.time_
 44 omega   70.00  178.00   1.0000    2.4700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0129012000
_diffrn_orient_matrix_UB_12      0.0433268000
_diffrn_orient_matrix_UB_13      -0.0966985000
_diffrn_orient_matrix_UB_21      0.2180616000
_diffrn_orient_matrix_UB_22      0.1262539000
_diffrn_orient_matrix_UB_23      0.0296890000
_diffrn_orient_matrix_UB_31      0.0456066000
_diffrn_orient_matrix_UB_32      -0.1575804000
_diffrn_orient_matrix_UB_33      -0.0263147000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2978
_reflns_number_total             3132
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.797
_refine_diff_density_min         -1.132
_refine_diff_density_rms         0.186
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0760P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.2174(18) 0.4747(19) 0.5385(7) 0.098(4) Uani 1 1 d . . . . .
H1A H 0.1732 0.5066 0.5871 0.147 Uiso 1 1 calc GR . . . .
H1B H 0.1108 0.4217 0.4845 0.147 Uiso 1 1 calc GR . . . .
H1C H 0.3160 0.5803 0.5277 0.147 Uiso 1 1 calc GR . . . .
C2 C 0.3005(10) 0.3407(13) 0.5641(4) 0.058(2) Uani 1 1 d . . . . .
C3 C 0.2467(11) 0.1866(15) 0.5039(5) 0.073(3) Uani 1 1 d . . . . .
H3 H 0.1594 0.1666 0.4476 0.087 Uiso 1 1 calc R . . . .
C4 C 0.3162(12) 0.0627(14) 0.5235(5) 0.069(2) Uani 1 1 d . . . . .
H4 H 0.2757 -0.0399 0.4813 0.083 Uiso 1 1 calc R . . . .
C5 C 0.4471(12) 0.0902(12) 0.6065(5) 0.0605(18) Uani 1 1 d . . . . .
H5 H 0.4972 0.0074 0.6201 0.073 Uiso 1 1 calc R . . . .
C6 C 0.5032(9) 0.2424(9) 0.6693(4) 0.0455(14) Uani 1 1 d . . . . .
H6 H 0.5926 0.2627 0.7250 0.055 Uiso 1 1 calc R . . . .
C7 C 0.4252(9) 0.3656(9) 0.6488(4) 0.0416(14) Uani 1 1 d . . . . .
C8 C 0.4721(8) 0.5155(9) 0.7218(4) 0.0395(14) Uani 1 1 d . . . . .
C9 C 0.5712(11) 0.6964(11) 0.7178(6) 0.0550(18) Uani 1 1 d . . . . .
H9 H 0.6171 0.7292 0.6679 0.066 Uiso 1 1 calc R . . . .
C10 C 0.6017(11) 0.8273(10) 0.7875(6) 0.0565(19) Uani 1 1 d . . . . .
H10 H 0.6641 0.9478 0.7835 0.068 Uiso 1 1 calc R . . . .
C11 C 0.5396(11) 0.7793(10) 0.8630(5) 0.0513(17) Uani 1 1 d . . . . .
H11 H 0.5590 0.8653 0.9106 0.062 Uiso 1 1 calc R . . . .
C12 C 0.4474(10) 0.5981(10) 0.8650(5) 0.0438(14) Uani 1 1 d . . . . .
H12 H 0.4072 0.5633 0.9159 0.053 Uiso 1 1 calc R . . . .
C13 C 0.1339(9) -0.0663(8) 0.8270(5) 0.0407(14) Uani 1 1 d . . . . .
C14 C 0.0939(11) -0.1039(12) 0.9075(6) 0.060(2) Uani 1 1 d . . . . .
H14 H 0.1228 -0.0132 0.9548 0.072 Uiso 1 1 calc R . . . .
C15 C 0.0071(14) -0.2862(15) 0.9157(7) 0.081(3) Uani 1 1 d . . . . .
H15 H -0.0231 -0.3175 0.9691 0.097 Uiso 1 1 calc R . . . .
C16 C -0.0331(12) -0.4174(12) 0.8454(8) 0.072(3) Uani 1 1 d . . . . .
H16 H -0.0904 -0.5373 0.8513 0.087 Uiso 1 1 calc R . . . .
C17 C 0.0105(14) -0.3731(12) 0.7669(8) 0.070(2) Uani 1 1 d . . . . .
H17 H -0.0157 -0.4635 0.7200 0.084 Uiso 1 1 calc R . . . .
C18 C 0.0932(11) -0.1957(11) 0.7556(6) 0.0547(18) Uani 1 1 d . . . . .
H18 H 0.1201 -0.1656 0.7014 0.066 Uiso 1 1 calc R . . . .
N1 N 0.4134(7) 0.4708(6) 0.7969(3) 0.0324(10) Uani 1 1 d . . . . .
Cl1 Cl -0.0156(2) 0.1657(2) 0.71437(13) 0.0518(4) Uani 1 1 d . . . . .
Cl2 Cl 0.5429(2) 0.2214(2) 0.91348(11) 0.0470(4) Uani 1 1 d . . . . .
Au1 Au 0.26685(3) 0.19528(3) 0.81184(2) 0.03340(13) 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.526(13) . ?
C2 C3 1.380(13) . ?
C2 C7 1.384(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.361(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.403(10) . ?
C7 C8 1.486(10) . ?
C8 C9 1.395(11) . ?
C8 N1 1.358(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(13) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(11) . ?
C12 H12 0.9300 . ?
C12 N1 1.338(9) . ?
C13 C14 1.370(10) . ?
C13 C18 1.369(11) . ?
C13 Au1 2.044(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.410(13) . ?
C15 H15 0.9300 . ?
C15 C16 1.368(16) . ?
C16 H16 0.9300 . ?
C16 C17 1.361(16) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(12) . ?
C18 H18 0.9300 . ?
N1 Au1 2.155(4) . ?
Cl1 Au1 2.2824(16) . ?
Cl2 Au1 2.2819(15) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.5(7) . . ?
C3 C2 C7 118.0(7) . . ?
C7 C2 C1 121.5(8) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 C2 122.8(7) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(8) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(8) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.1(6) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 120.0(7) . . ?
C2 C7 C8 121.8(6) . . ?
C6 C7 C8 118.1(6) . . ?
C9 C8 C7 124.4(6) . . ?
N1 C8 C7 116.9(5) . . ?
N1 C8 C9 118.7(7) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(7) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(7) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 121.3 . . ?
C10 C11 C12 117.3(7) . . ?
C12 C11 H11 121.3 . . ?
C11 C12 H12 118.5 . . ?
N1 C12 C11 123.0(7) . . ?
N1 C12 H12 118.5 . . ?
C14 C13 Au1 119.2(6) . . ?
C18 C13 C14 123.3(7) . . ?
C18 C13 Au1 117.5(5) . . ?
C13 C14 H14 121.4 . . ?
C13 C14 C15 117.1(9) . . ?
C15 C14 H14 121.4 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(9) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(9) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.2(10) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C17 117.7(8) . . ?
C13 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
C8 N1 Au1 121.7(4) . . ?
C12 N1 C8 120.5(6) . . ?
C12 N1 Au1 117.8(4) . . ?
C13 Au1 N1 178.69(19) . . ?
C13 Au1 Cl1 89.65(19) . . ?
C13 Au1 Cl2 89.11(19) . . ?
N1 Au1 Cl1 91.57(14) . . ?
N1 Au1 Cl2 89.69(14) . . ?
Cl2 Au1 Cl1 177.75(5) . . ?

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
C1 C2 C3 C4 -179.8(9) . . . . ?
C1 C2 C7 C6 -178.2(8) . . . . ?
C1 C2 C7 C8 5.1(11) . . . . ?
C2 C3 C4 C5 -0.4(13) . . . . ?
C2 C7 C8 C9 -64.8(9) . . . . ?
C2 C7 C8 N1 115.1(7) . . . . ?
C3 C2 C7 C6 4.2(10) . . . . ?
C3 C2 C7 C8 -172.4(6) . . . . ?
C3 C4 C5 C6 1.1(12) . . . . ?
C4 C5 C6 C7 0.9(11) . . . . ?
C5 C6 C7 C2 -3.6(9) . . . . ?
C5 C6 C7 C8 173.2(6) . . . . ?
C6 C7 C8 C9 118.4(7) . . . . ?
C6 C7 C8 N1 -61.6(8) . . . . ?
C7 C2 C3 C4 -2.3(12) . . . . ?
C7 C8 C9 C10 177.4(7) . . . . ?
C7 C8 N1 C12 -178.9(6) . . . . ?
C7 C8 N1 Au1 1.9(7) . . . . ?
C8 C9 C10 C11 2.1(12) . . . . ?
C9 C8 N1 C12 1.0(9) . . . . ?
C9 C8 N1 Au1 -178.1(5) . . . . ?
C9 C10 C11 C12 -0.1(12) . . . . ?
C10 C11 C12 N1 -1.5(12) . . . . ?
C11 C12 N1 C8 1.0(10) . . . . ?
C11 C12 N1 Au1 -179.8(6) . . . . ?
C13 C14 C15 C16 0.4(13) . . . . ?
C14 C13 C18 C17 -1.2(12) . . . . ?
C14 C15 C16 C17 0.0(14) . . . . ?
C15 C16 C17 C18 -1.0(15) . . . . ?
C16 C17 C18 C13 1.6(13) . . . . ?
C18 C13 C14 C15 0.2(12) . . . . ?
N1 C8 C9 C10 -2.6(11) . . . . ?
Au1 C13 C14 C15 -178.3(6) . . . . ?
Au1 C13 C18 C17 177.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1019879'
