# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_c052
_audit_block_doi                 10.5517/cc13k6rm
_database_code_depnum_ccdc_archive 'CCDC 1029440'
_audit_update_record             
;
2014-12-05 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 Au Br0.50 Cl N3'
_chemical_formula_weight         445.59

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'
Br Br -0.2901 2.4595 '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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8063(6)
_cell_length_b                   9.4869(9)
_cell_length_c                   9.6535(9)
_cell_angle_alpha                106.0990(10)
_cell_angle_beta                 103.6680(10)
_cell_angle_gamma                91.5240(10)
_cell_volume                     579.09(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5417
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.35

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    2.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             411
_exptl_absorpt_coefficient_mu    14.629
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3129
_exptl_absorpt_correction_T_max  0.4312
_exptl_absorpt_process_details   
;
'SADABS v.1.0 (Bruker,2008) was used for absorption correction. 
R(int) was 0.0654 before and 0.0371 after correction. The Ratio of 
minimum to maximum transmission is 0.7256. The l/2 correction factor 
is 0.0015'
;

_exptl_special_details           
; 
?
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7696
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2657
_reflns_number_gt                2575
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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. 

The Cl atom was disordered with  partially  replaced by Br . The occupancy
ratio of Cl : Br is 81:19.  Restraints in thermal parameters(EADP of
Shelxtl program ) and bond lengths (DFIX of Shelxtl program) were applied 
to the disordered atoms. 
;

_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)+(0.0223P)²+0.0000P] 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         2657
_refine_ls_number_parameters     141
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0180
_refine_ls_wR_factor_ref         0.0456
_refine_ls_wR_factor_gt          0.0453
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.751517(17) 0.526793(12) 0.984172(13) 0.01720(5) Uani 1 1 d D . .
Cl1 Cl 0.7601(19) 0.7314(11) 0.9059(11) 0.0195(8) Uani 0.808(3) 1 d PD . .
Br1 Br 0.764(3) 0.7326(19) 0.886(2) 0.0195(8) Uani 0.192(3) 1 d PD . .
N1 N 0.7404(4) 0.2078(3) 0.9699(3) 0.0192(6) Uani 1 1 d . . .
N2 N 0.7484(5) 0.1975(3) 1.1967(3) 0.0232(6) Uani 1 1 d . . .
N3 N 0.7482(4) 0.3391(3) 1.1878(3) 0.0211(6) Uani 1 1 d . . .
C1 C 0.7444(5) 0.3495(4) 1.0519(4) 0.0163(6) Uani 1 1 d . . .
C2 C 0.7454(5) 0.1205(4) 1.0614(4) 0.0246(7) Uani 1 1 d . . .
H2 H 0.7465 0.0164 1.0302 0.030 Uiso 1 1 calc R . .
C3 C 0.7441(6) 0.4596(4) 1.3184(4) 0.0301(8) Uani 1 1 d . . .
H3A H 0.7553 0.5536 1.2958 0.045 Uiso 1 1 calc R . .
H3B H 0.8583 0.4582 1.4015 0.045 Uiso 1 1 calc R . .
H3C H 0.6161 0.4482 1.3457 0.045 Uiso 1 1 calc R . .
C4 C 0.7560(5) 0.1600(4) 0.8161(4) 0.0232(7) Uani 1 1 d . . .
H4A H 0.7872 0.0560 0.7921 0.028 Uiso 1 1 calc R . .
H4B H 0.8711 0.2199 0.8070 0.028 Uiso 1 1 calc R . .
C5 C 0.5674(5) 0.1726(4) 0.7037(4) 0.0195(7) Uani 1 1 d . . .
C6 C 0.5845(6) 0.2057(4) 0.5751(4) 0.0255(8) Uani 1 1 d . . .
H6 H 0.7152 0.2279 0.5630 0.031 Uiso 1 1 calc R . .
C7 C 0.4144(6) 0.2065(4) 0.4654(4) 0.0291(8) Uani 1 1 d . . .
H7 H 0.4290 0.2288 0.3781 0.035 Uiso 1 1 calc R . .
C8 C 0.2242(6) 0.1756(4) 0.4804(4) 0.0271(8) Uani 1 1 d . . .
H8 H 0.1070 0.1767 0.4045 0.032 Uiso 1 1 calc R . .
C9 C 0.2052(5) 0.1428(4) 0.6077(4) 0.0244(7) Uani 1 1 d . . .
H9 H 0.0738 0.1210 0.6189 0.029 Uiso 1 1 calc R . .
C10 C 0.3748(5) 0.1413(4) 0.7190(4) 0.0233(7) Uani 1 1 d . . .
H10 H 0.3595 0.1188 0.8061 0.028 Uiso 1 1 calc R . .


_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 C1 1.970(3) . ?
Au1 Cl1 2.274(8) . ?
Au1 Br1 2.402(13) . ?
N1 C1 1.353(4) . ?
N1 C2 1.364(5) . ?
N1 C4 1.458(4) . ?
N2 C2 1.303(5) . ?
N2 N3 1.370(4) . ?
N3 C1 1.337(4) . ?
N3 C3 1.455(4) . ?
C2 H2 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.504(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.387(5) . ?
C5 C6 1.391(5) . ?
C6 C7 1.374(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.370(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

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
C1 Au1 Cl1 179.9(3) . . ?
C1 Au1 Br1 176.1(5) . . ?
Cl1 Au1 Br1 3.8(7) . . ?
C1 N1 C2 108.1(3) . . ?
C1 N1 C4 125.4(3) . . ?
C2 N1 C4 126.0(3) . . ?
C2 N2 N3 102.9(3) . . ?
C1 N3 N2 113.7(3) . . ?
C1 N3 C3 126.6(3) . . ?
N2 N3 C3 119.7(3) . . ?
N3 C1 N1 103.6(3) . . ?
N3 C1 Au1 129.2(3) . . ?
N1 C1 Au1 127.2(2) . . ?
N2 C2 N1 111.7(3) . . ?
N2 C2 H2 124.2 . . ?
N1 C2 H2 124.2 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 114.1(3) . . ?
N1 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
N1 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C10 C5 C6 118.5(3) . . ?
C10 C5 C4 121.7(3) . . ?
C6 C5 C4 119.6(3) . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.0(4) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C8 C9 C10 120.9(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C5 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.235
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.140
####################################################################### 
# 
# 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_E090
_audit_block_doi                 10.5517/cc13k6sn
_database_code_depnum_ccdc_archive 'CCDC 1029441'
_audit_update_record             
;
2014-12-05 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 Au Br N3'
_chemical_formula_weight         450.09

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'
Br Br -0.2901 2.4595 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.879(2)
_cell_length_b                   10.971(2)
_cell_length_c                   12.044(2)
_cell_angle_alpha                77.756(3)
_cell_angle_beta                 69.925(3)
_cell_angle_gamma                60.903(3)
_cell_volume                     1178.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    924
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    2.538
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    15.850
_shelx_estimated_absorpt_T_min   0.052
_shelx_estimated_absorpt_T_max   0.252
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3733
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
'SADABS v1.00 (Bruker,2008) was used for absorption correction. 
R(int) was 0.1225 before and 0.0440 after correction. The Ratio of 
minimum to maximum transmission is 0.5007. The l/2 correction factor 
is 0.0015'
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15052
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.803
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5398
_reflns_number_gt                5105
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0140P)²+0.9394P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5398
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0500
_refine_ls_wR_factor_gt          0.0493
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.60084(2) 0.00592(2) 0.57284(2) 0.01156(4) Uani 1 1 d . . . . .
Au2 Au 0.12042(2) 0.30434(2) 0.21373(2) 0.01347(4) Uani 1 1 d . . . . .
Br1 Br 0.85200(4) -0.11899(4) 0.46016(3) 0.01578(8) Uani 1 1 d . . . . .
Br2 Br 0.20946(4) 0.43868(4) 0.26722(3) 0.02000(9) Uani 1 1 d . . . . .
N1 N 0.3006(3) 0.2467(3) 0.6588(3) 0.0122(6) Uani 1 1 d . . . . .
N2 N 0.3277(3) 0.0660(3) 0.7747(3) 0.0137(6) Uani 1 1 d . . . . .
N3 N 0.1888(3) 0.1667(3) 0.8236(3) 0.0166(7) Uani 1 1 d . . . . .
N4 N 0.0619(3) 0.0661(3) 0.2016(3) 0.0123(6) Uani 1 1 d . . . . .
N5 N -0.0466(3) 0.2434(3) 0.0986(3) 0.0156(6) Uani 1 1 d . . . . .
N6 N -0.0846(3) 0.1451(3) 0.0872(3) 0.0178(7) Uani 1 1 d . . . . .
C1 C 0.3980(4) 0.1118(4) 0.6736(3) 0.0119(7) Uani 1 1 d . . . . .
C2 C 0.1764(4) 0.2747(4) 0.7496(3) 0.0162(8) Uani 1 1 d . . . . .
H2 H 0.0912 0.3622 0.7581 0.019 Uiso 1 1 calc R U . . .
C3 C 0.3178(4) 0.3413(4) 0.5546(3) 0.0168(8) Uani 1 1 d . . . . .
H3A H 0.2403 0.3675 0.5164 0.020 Uiso 1 1 calc R U . . .
H3B H 0.4138 0.2913 0.4969 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3093(4) 0.4726(4) 0.5847(3) 0.0135(7) Uani 1 1 d . . . . .
C5 C 0.3986(4) 0.4643(4) 0.6487(3) 0.0159(7) Uani 1 1 d . . . . .
H5 H 0.4614 0.3760 0.6774 0.019 Uiso 1 1 calc R U . . .
C6 C 0.3956(4) 0.5849(4) 0.6703(3) 0.0189(8) Uani 1 1 d . . . . .
H6 H 0.4565 0.5791 0.7139 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3038(4) 0.7143(4) 0.6284(3) 0.0198(8) Uani 1 1 d . . . . .
H7 H 0.3024 0.7968 0.6429 0.024 Uiso 1 1 calc R U . . .
C8 C 0.2147(4) 0.7230(4) 0.5655(3) 0.0188(8) Uani 1 1 d . . . . .
H8 H 0.1520 0.8116 0.5369 0.023 Uiso 1 1 calc R U . . .
C9 C 0.2164(4) 0.6027(4) 0.5440(3) 0.0164(8) Uani 1 1 d . . . . .
H9 H 0.1541 0.6091 0.5015 0.020 Uiso 1 1 calc R U . . .
C10 C 0.3806(4) -0.0727(4) 0.8328(3) 0.0180(8) Uani 1 1 d . . . . .
H10A H 0.4841 -0.1286 0.7923 0.027 Uiso 1 1 calc R U . . .
H10B H 0.3232 -0.1179 0.8298 0.027 Uiso 1 1 calc R U . . .
H10C H 0.3701 -0.0653 0.9155 0.027 Uiso 1 1 calc R U . . .
C11 C 0.0421(4) 0.1993(4) 0.1673(3) 0.0138(7) Uani 1 1 d . . . . .
C12 C -0.0155(4) 0.0381(4) 0.1510(3) 0.0162(7) Uani 1 1 d . . . . .
H12 H -0.0186 -0.0487 0.1610 0.019 Uiso 1 1 calc R U . . .
C13 C 0.1564(4) -0.0334(4) 0.2757(3) 0.0136(7) Uani 1 1 d . . . . .
H13A H 0.1043 -0.0826 0.3353 0.016 Uiso 1 1 calc R U . . .
H13B H 0.1787 0.0179 0.3183 0.016 Uiso 1 1 calc R U . . .
C14 C 0.2967(4) -0.1381(4) 0.2004(3) 0.0112(7) Uani 1 1 d . . . . .
C15 C 0.3078(5) -0.2643(4) 0.1795(4) 0.0215(8) Uani 1 1 d . . . . .
H15 H 0.2288 -0.2872 0.2180 0.026 Uiso 1 1 calc R U . . .
C16 C 0.4332(5) -0.3558(4) 0.1032(4) 0.0293(10) Uani 1 1 d . . . . .
H16 H 0.4400 -0.4410 0.0886 0.035 Uiso 1 1 calc R U . . .
C17 C 0.5479(5) -0.3233(5) 0.0483(4) 0.0296(11) Uani 1 1 d . . . . .
H17 H 0.6333 -0.3858 -0.0049 0.035 Uiso 1 1 calc R U . . .
C18 C 0.5401(4) -0.2001(5) 0.0699(4) 0.0246(9) Uani 1 1 d . . . . .
H18 H 0.6208 -0.1794 0.0329 0.029 Uiso 1 1 calc R U . . .
C19 C 0.4143(4) -0.1070(4) 0.1456(3) 0.0168(8) Uani 1 1 d . . . . .
H19 H 0.4084 -0.0222 0.1600 0.020 Uiso 1 1 calc R U . . .
C20 C -0.1081(5) 0.3816(4) 0.0407(4) 0.0245(9) Uani 1 1 d . . . . .
H20A H -0.1965 0.4444 0.0966 0.037 Uiso 1 1 calc R U . . .
H20B H -0.1333 0.3753 -0.0279 0.037 Uiso 1 1 calc R U . . .
H20C H -0.0358 0.4181 0.0144 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 1.989(4) . ?
Au1 Br1 2.4057(5) . ?
Au1 Au1 3.3057(5) 2_656 ?
Au2 C11 1.981(4) . ?
Au2 Br2 2.3970(5) . ?
N1 C1 1.356(5) . ?
N1 C2 1.356(5) . ?
N1 C3 1.470(4) . ?
N2 C1 1.340(5) . ?
N2 N3 1.376(4) . ?
N2 C10 1.453(5) . ?
N3 C2 1.303(5) . ?
N4 C11 1.361(5) . ?
N4 C12 1.363(5) . ?
N4 C13 1.473(4) . ?
N5 C11 1.332(5) . ?
N5 N6 1.374(4) . ?
N5 C20 1.456(5) . ?
N6 C12 1.299(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.511(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.392(5) . ?
C4 C5 1.394(5) . ?
C5 C6 1.384(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12 0.9500 . ?
C13 C14 1.503(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.392(5) . ?
C14 C15 1.399(5) . ?
C15 C16 1.383(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C1 Au1 Br1 176.15(10) . . ?
C1 Au1 Au1 77.62(10) . 2_656 ?
Br1 Au1 Au1 106.230(18) . 2_656 ?
C11 Au2 Br2 178.05(10) . . ?
C1 N1 C2 108.3(3) . . ?
C1 N1 C3 126.0(3) . . ?
C2 N1 C3 125.2(3) . . ?
C1 N2 N3 112.7(3) . . ?
C1 N2 C10 127.8(3) . . ?
N3 N2 C10 119.5(3) . . ?
C2 N3 N2 103.5(3) . . ?
C11 N4 C12 108.2(3) . . ?
C11 N4 C13 126.1(3) . . ?
C12 N4 C13 125.7(3) . . ?
C11 N5 N6 113.8(3) . . ?
C11 N5 C20 127.1(3) . . ?
N6 N5 C20 119.1(3) . . ?
C12 N6 N5 103.1(3) . . ?
N2 C1 N1 103.9(3) . . ?
N2 C1 Au1 127.4(3) . . ?
N1 C1 Au1 128.7(3) . . ?
N3 C2 N1 111.5(3) . . ?
N3 C2 H2 124.2 . . ?
N1 C2 H2 124.2 . . ?
N1 C3 C4 113.0(3) . . ?
N1 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
N1 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C9 C4 C5 119.6(3) . . ?
C9 C4 C3 119.9(3) . . ?
C5 C4 C3 120.4(3) . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C4 120.1(3) . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 N4 103.4(3) . . ?
N5 C11 Au2 128.4(3) . . ?
N4 C11 Au2 128.2(3) . . ?
N6 C12 N4 111.6(3) . . ?
N6 C12 H12 124.2 . . ?
N4 C12 H12 124.2 . . ?
N4 C13 C14 110.3(3) . . ?
N4 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N4 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C19 C14 C15 119.4(4) . . ?
C19 C14 C13 120.1(3) . . ?
C15 C14 C13 120.4(3) . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.9(4) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.7(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 119.9(4) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
N5 C20 H20A 109.5 . . ?
N5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         1.046
_refine_diff_density_min         -1.673
_refine_diff_density_rms         0.164

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_b115
_audit_block_doi                 10.5517/cc13k6tp
_database_code_depnum_ccdc_archive 'CCDC 1029442'
_audit_update_record             
;
2014-12-05 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Au2 I2 N6'
_chemical_formula_weight         994.17

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6322(5)
_cell_length_b                   8.7311(7)
_cell_length_c                   11.7798(9)
_cell_angle_alpha                69.501(2)
_cell_angle_beta                 87.692(2)
_cell_angle_gamma                72.119(2)
_cell_volume                     606.34(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3448
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.27

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    2.723
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    14.649
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.1611
_exptl_absorpt_correction_T_max  0.3630
_exptl_absorpt_process_details   
;
'SADABS v.1.0 (Bruker,2008) was used for absorption correction. 
R(int) was 0.1285 before and 0.0480 after correction. The Ratio of 
minimum to maximum transmission is 0.4438. The l/2 correction factor 
is 0.0015'
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7791
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2778
_reflns_number_gt                2551
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0320P)²+0.4169P] 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         2778
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.007

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 0.0000 1.0000 1.0000 0.03405(10) Uani 1 2 d S . .
Au2 Au 0.5000 1.0000 1.0000 0.03996(11) Uani 1 2 d S . .
I1 I 0.51193(6) 0.82317(5) 1.22612(4) 0.03974(11) Uani 1 1 d . . .
N1 N 0.1904(8) 0.7163(6) 0.8947(4) 0.0397(11) Uani 1 1 d . . .
N2 N 0.1533(6) 0.6117(5) 1.0836(4) 0.0296(9) Uani 1 1 d . . .
N3 N 0.2407(7) 0.4719(6) 1.0488(5) 0.0378(11) Uani 1 1 d . . .
C1 C 0.1224(8) 0.7621(6) 0.9909(5) 0.0299(11) Uani 1 1 d . . .
C2 C 0.2618(10) 0.5393(8) 0.9354(6) 0.0398(13) Uani 1 1 d . . .
H2 H 0.3195 0.4753 0.8855 0.048 Uiso 1 1 calc R . .
C3 C 0.2069(15) 0.8336(10) 0.7722(6) 0.067(2) Uani 1 1 d . . .
H3A H 0.3563 0.8270 0.7614 0.081 Uiso 1 1 calc R . .
H3B H 0.1274 0.9519 0.7651 0.081 Uiso 1 1 calc R . .
C4 C 0.1237(10) 0.7932(7) 0.6730(5) 0.0373(13) Uani 1 1 d . . .
C5 C -0.0908(11) 0.8537(7) 0.6376(6) 0.0503(17) Uani 1 1 d . . .
H5 H -0.1869 0.9193 0.6767 0.060 Uiso 1 1 calc R . .
C6 C -0.1647(11) 0.8173(9) 0.5440(7) 0.0580(19) Uani 1 1 d . . .
H6 H -0.3106 0.8588 0.5198 0.070 Uiso 1 1 calc R . .
C7 C -0.0275(13) 0.7227(9) 0.4879(6) 0.0568(18) Uani 1 1 d . . .
H7 H -0.0782 0.6980 0.4251 0.068 Uiso 1 1 calc R . .
C8 C 0.1836(12) 0.6629(8) 0.5219(6) 0.0517(16) Uani 1 1 d . . .
H8 H 0.2785 0.5972 0.4824 0.062 Uiso 1 1 calc R . .
C9 C 0.2591(10) 0.6981(8) 0.6137(6) 0.0440(14) Uani 1 1 d . . .
H9 H 0.4056 0.6564 0.6363 0.053 Uiso 1 1 calc R . .
C10 C 0.1099(9) 0.5865(7) 1.2096(5) 0.0376(12) Uani 1 1 d . . .
H10A H 0.2393 0.5164 1.2614 0.056 Uiso 1 1 calc R . .
H10B H 0.0027 0.5288 1.2318 0.056 Uiso 1 1 calc R . .
H10C H 0.0589 0.6973 1.2197 0.056 Uiso 1 1 calc R . .


_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 C1 2.024(5) . ?
Au1 C1 2.024(5) 2_577 ?
Au1 Au2 3.3161(3) 1_455 ?
Au1 Au2 3.3161(3) . ?
Au2 I1 2.5586(4) . ?
Au2 I1 2.5586(4) 2_677 ?
Au2 Au1 3.3161(3) 1_655 ?
N1 C1 1.346(7) . ?
N1 C2 1.376(8) . ?
N1 C3 1.471(8) . ?
N2 C1 1.344(7) . ?
N2 N3 1.375(6) . ?
N2 C10 1.453(7) . ?
N3 C2 1.279(9) . ?
C3 C4 1.502(9) . ?
C4 C9 1.372(8) . ?
C4 C5 1.381(9) . ?
C5 C6 1.394(10) . ?
C6 C7 1.348(11) . ?
C7 C8 1.357(10) . ?
C8 C9 1.374(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
C1 Au1 C1 180.0(3) . 2_577 ?
C1 Au1 Au2 94.81(14) . 1_455 ?
C1 Au1 Au2 85.19(14) 2_577 1_455 ?
C1 Au1 Au2 85.19(14) . . ?
C1 Au1 Au2 94.81(14) 2_577 . ?
Au2 Au1 Au2 180.0 1_455 . ?
I1 Au2 I1 180.000(1) . 2_677 ?
I1 Au2 Au1 83.545(9) . . ?
I1 Au2 Au1 96.455(9) 2_677 . ?
I1 Au2 Au1 96.455(9) . 1_655 ?
I1 Au2 Au1 83.545(9) 2_677 1_655 ?
Au1 Au2 Au1 180.0 . 1_655 ?
C1 N1 C2 107.3(5) . . ?
C1 N1 C3 126.1(5) . . ?
C2 N1 C3 126.3(5) . . ?
C1 N2 N3 112.5(4) . . ?
C1 N2 C10 127.4(5) . . ?
N3 N2 C10 120.1(4) . . ?
C2 N3 N2 103.7(5) . . ?
N2 C1 N1 104.3(4) . . ?
N2 C1 Au1 126.3(4) . . ?
N1 C1 Au1 129.4(4) . . ?
N3 C2 N1 112.2(5) . . ?
N1 C3 C4 113.0(5) . . ?
C9 C4 C5 118.3(6) . . ?
C9 C4 C3 120.8(6) . . ?
C5 C4 C3 120.8(6) . . ?
C4 C5 C6 120.0(6) . . ?
C7 C6 C5 120.2(6) . . ?
C6 C7 C8 120.2(6) . . ?
C7 C8 C9 120.3(6) . . ?
C4 C9 C8 120.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.355
_refine_diff_density_min         -1.144
_refine_diff_density_rms         0.164
####################################################################### 
# 
# 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_c057
_audit_block_doi                 10.5517/cc13k6vq
_database_code_depnum_ccdc_archive 'CCDC 1029443'
_audit_update_record             
;
2014-12-05 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14.50 Au N3 O2.25'
_chemical_formula_weight         433.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.7892(15)
_cell_length_b                   8.7330(14)
_cell_length_c                   16.171(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.757(2)
_cell_angle_gamma                90.00
_cell_volume                     1336.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5569
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.41

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             818
_exptl_absorpt_coefficient_mu    11.005
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.0962
_exptl_absorpt_correction_T_max  0.2169
_exptl_absorpt_process_details   
;
'SADABS v2.10 (Bruker,2008) was used for absorption correction. 
R(int) was 0.1685 before and 0.0352 after correction. The Ratio of 
minimum to maximum transmission is 0.3665. The l/2 correction factor 
is 0.0015'
;

_exptl_special_details           
; 
?
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9332
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3068
_reflns_number_gt                2814
_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. 

H atoms of the partially occupied water were not located.
;

_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)+(0.0398P)²+0.2808P] 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         3068
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0652
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.003
_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 0.141158(15) 0.074862(14) 0.577055(8) 0.01644(7) Uani 1 1 d . . .
O1 O 0.2560(3) 0.0922(3) 0.4885(2) 0.0256(7) Uani 1 1 d . . .
O2 O 0.4110(4) 0.2576(4) 0.5660(3) 0.0501(10) Uani 1 1 d . . .
N1 N 0.0670(3) -0.0348(4) 0.7355(2) 0.0171(6) Uani 1 1 d . . .
N2 N -0.0883(3) 0.1179(4) 0.6665(2) 0.0194(6) Uani 1 1 d . . .
N3 N -0.1337(4) 0.0781(3) 0.7364(2) 0.0236(8) Uani 1 1 d . . .
C1 C 0.0312(4) 0.0508(4) 0.6636(3) 0.0160(7) Uani 1 1 d . . .
C2 C -0.0358(4) -0.0156(5) 0.7770(3) 0.0233(8) Uani 1 1 d . . .
H2 H -0.0365 -0.0646 0.8294 0.028 Uiso 1 1 calc R . .
C3 C 0.1927(4) -0.1336(4) 0.7640(2) 0.0191(7) Uani 1 1 d . . .
H3A H 0.2037 -0.1969 0.7153 0.023 Uiso 1 1 calc R . .
H3B H 0.1786 -0.2036 0.8093 0.023 Uiso 1 1 calc R . .
C4 C 0.3248(4) -0.0417(4) 0.7978(2) 0.0158(7) Uani 1 1 d . . .
C5 C 0.3530(4) 0.0266(5) 0.8778(2) 0.0203(7) Uani 1 1 d . . .
H5 H 0.2902 0.0126 0.9134 0.024 Uiso 1 1 calc R . .
C6 C 0.4745(5) 0.1163(5) 0.9058(3) 0.0269(9) Uani 1 1 d . . .
H6 H 0.4931 0.1642 0.9603 0.032 Uiso 1 1 calc R . .
C7 C 0.5666(4) 0.1360(5) 0.8560(3) 0.0277(9) Uani 1 1 d . . .
H7 H 0.6480 0.1984 0.8754 0.033 Uiso 1 1 calc R . .
C8 C 0.5412(5) 0.0647(4) 0.7766(3) 0.0266(9) Uani 1 1 d . . .
H8 H 0.6062 0.0764 0.7423 0.032 Uiso 1 1 calc R . .
C9 C 0.4206(4) -0.0238(5) 0.7476(2) 0.0201(7) Uani 1 1 d . . .
H9 H 0.4032 -0.0724 0.6934 0.024 Uiso 1 1 calc R . .
C10 C -0.1744(4) 0.2225(5) 0.6041(3) 0.0260(8) Uani 1 1 d . . .
H10A H -0.1459 0.3282 0.6198 0.039 Uiso 1 1 calc R . .
H10B H -0.2742 0.2091 0.6031 0.039 Uiso 1 1 calc R . .
H10C H -0.1610 0.2002 0.5472 0.039 Uiso 1 1 calc R . .
C11 C 0.3659(5) 0.1787(5) 0.5022(3) 0.0287(9) Uani 1 1 d . . .
C12 C 0.4420(5) 0.1737(7) 0.4315(3) 0.0419(12) Uani 1 1 d . . .
H12A H 0.5321 0.2282 0.4500 0.063 Uiso 1 1 calc R . .
H12B H 0.3834 0.2227 0.3801 0.063 Uiso 1 1 calc R . .
H12C H 0.4597 0.0669 0.4188 0.063 Uiso 1 1 calc R . .
O1W O 0.6012(19) 0.4619(18) 0.5240(12) 0.057(4) Uani 0.25 1 d P . .


_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 C1 1.981(4) . ?
Au1 O1 2.039(3) . ?
O1 C11 1.287(6) . ?
O2 C11 1.226(6) . ?
N1 C1 1.352(5) . ?
N1 C2 1.355(5) . ?
N1 C3 1.477(5) . ?
N2 C1 1.321(5) . ?
N2 N3 1.361(5) . ?
N2 C10 1.460(5) . ?
N3 C2 1.304(5) . ?
C3 C4 1.502(5) . ?
C4 C5 1.387(5) . ?
C4 C9 1.397(5) . ?
C5 C6 1.400(6) . ?
C6 C7 1.365(6) . ?
C7 C8 1.391(6) . ?
C8 C9 1.389(6) . ?
C11 C12 1.516(6) . ?

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
C1 Au1 O1 178.12(13) . . ?
C11 O1 Au1 120.6(3) . . ?
C1 N1 C2 107.2(3) . . ?
C1 N1 C3 127.2(3) . . ?
C2 N1 C3 125.6(3) . . ?
C1 N2 N3 113.4(3) . . ?
C1 N2 C10 127.8(3) . . ?
N3 N2 C10 118.8(3) . . ?
C2 N3 N2 103.0(3) . . ?
N2 C1 N1 104.6(3) . . ?
N2 C1 Au1 128.6(3) . . ?
N1 C1 Au1 126.7(3) . . ?
N3 C2 N1 111.8(4) . . ?
N1 C3 C4 111.9(3) . . ?
C5 C4 C9 119.4(4) . . ?
C5 C4 C3 121.2(3) . . ?
C9 C4 C3 119.4(3) . . ?
C4 C5 C6 119.5(4) . . ?
C7 C6 C5 121.0(4) . . ?
C6 C7 C8 119.9(4) . . ?
C9 C8 C7 119.8(4) . . ?
C8 C9 C4 120.4(4) . . ?
O2 C11 O1 125.6(4) . . ?
O2 C11 C12 120.6(4) . . ?
O1 C11 C12 113.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.538
_refine_diff_density_min         -1.623
_refine_diff_density_rms         0.199
####################################################################### 
# 
# 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_c367
_audit_block_doi                 10.5517/cc13k6wr
_database_code_depnum_ccdc_archive 'CCDC 1029444'
_audit_update_record             
;
2014-12-05 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Au F6 N6 P'
_chemical_formula_weight         688.37

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'
F F 0.0171 0.0103 '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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.0153(6)
_cell_length_b                   11.3120(8)
_cell_length_c                   12.4710(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.9850(10)
_cell_angle_gamma                90.00
_cell_volume                     1130.57(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3898
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.52

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    2.022
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    6.648
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.1358
_exptl_absorpt_correction_T_max  0.5561
_exptl_absorpt_process_details   
;
'SADABS v1.00 (Bruker,2008) was used for absorption correction. 
R(int) was 0.1074 before and 0.0460 after correction. The Ratio of 
minimum to maximum transmission is 0.4713. The l/2 correction factor 
is 0.0015'
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7835
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2592
_reflns_number_gt                2046
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0459P)²+0.0000P] 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         2592
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.5000 0.0000 0.5000 0.01513(10) Uani 1 2 d S . .
N1 N 0.8310(4) 0.1314(3) 0.5462(2) 0.0157(7) Uani 1 1 d . . .
N2 N 0.8183(4) 0.0596(3) 0.3902(2) 0.0159(7) Uani 1 1 d . . .
N3 N 0.9690(4) 0.1162(3) 0.3953(3) 0.0206(7) Uani 1 1 d . . .
C1 C 0.7305(4) 0.0672(3) 0.4802(3) 0.0151(7) Uani 1 1 d . . .
C2 C 0.9724(4) 0.1590(4) 0.4922(3) 0.0186(9) Uani 1 1 d . . .
H2 H 1.0622 0.2039 0.5217 0.022 Uiso 1 1 calc R . .
C3 C 0.8038(5) 0.1568(4) 0.6602(3) 0.0181(8) Uani 1 1 d . . .
H3A H 0.8960 0.2074 0.6874 0.022 Uiso 1 1 calc R . .
H3B H 0.8080 0.0816 0.7008 0.022 Uiso 1 1 calc R . .
C4 C 0.6400(5) 0.2175(3) 0.6818(3) 0.0160(8) Uani 1 1 d . . .
C5 C 0.5664(5) 0.2021(4) 0.7814(3) 0.0198(8) Uani 1 1 d . . .
H5 H 0.6177 0.1513 0.8328 0.024 Uiso 1 1 calc R . .
C6 C 0.4211(5) 0.2592(4) 0.8063(4) 0.0235(9) Uani 1 1 d . . .
H6 H 0.3735 0.2484 0.8748 0.028 Uiso 1 1 calc R . .
C7 C 0.3444(5) 0.3319(4) 0.7327(4) 0.0243(9) Uani 1 1 d . . .
H7 H 0.2425 0.3699 0.7495 0.029 Uiso 1 1 calc R . .
C8 C 0.4165(5) 0.3501(4) 0.6324(3) 0.0239(9) Uani 1 1 d . . .
H8 H 0.3645 0.4009 0.5812 0.029 Uiso 1 1 calc R . .
C9 C 0.5643(5) 0.2933(3) 0.6088(3) 0.0206(8) Uani 1 1 d . . .
H9 H 0.6146 0.3065 0.5414 0.025 Uiso 1 1 calc R . .
C10 C 0.7687(7) -0.0015(3) 0.2919(4) 0.0236(10) Uani 1 1 d . . .
H10A H 0.6505 -0.0230 0.2951 0.035 Uiso 1 1 calc R . .
H10B H 0.8360 -0.0732 0.2841 0.035 Uiso 1 1 calc R . .
H10C H 0.7862 0.0506 0.2303 0.035 Uiso 1 1 calc R . .
P1 P 0.0000 0.5000 0.5000 0.0155(3) Uani 1 2 d S . .
F1 F 0.0056(3) 0.5950(2) 0.40488(18) 0.0265(6) Uani 1 1 d . . .
F2 F 0.1412(3) 0.5713(2) 0.5644(2) 0.0318(6) Uani 1 1 d . . .
F3 F -0.1398(3) 0.5773(2) 0.55731(18) 0.0262(5) 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
Au1 C1 2.017(4) 3_656 ?
Au1 C1 2.017(4) . ?
N1 C1 1.353(5) . ?
N1 C2 1.365(5) . ?
N1 C3 1.471(5) . ?
N2 C1 1.339(5) . ?
N2 N3 1.367(4) . ?
N2 C10 1.457(6) . ?
N3 C2 1.301(5) . ?
C3 C4 1.510(5) . ?
C4 C9 1.382(5) . ?
C4 C5 1.396(6) . ?
C5 C6 1.372(6) . ?
C6 C7 1.370(6) . ?
C7 C8 1.401(6) . ?
C8 C9 1.384(5) . ?
P1 F2 1.595(2) . ?
P1 F2 1.595(2) 3_566 ?
P1 F3 1.600(2) . ?
P1 F3 1.600(2) 3_566 ?
P1 F1 1.602(2) . ?
P1 F1 1.602(2) 3_566 ?

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
C1 Au1 C1 180.0(2) 3_656 . ?
C1 N1 C2 108.3(3) . . ?
C1 N1 C3 126.6(3) . . ?
C2 N1 C3 124.8(3) . . ?
C1 N2 N3 114.0(3) . . ?
C1 N2 C10 126.6(3) . . ?
N3 N2 C10 119.3(3) . . ?
C2 N3 N2 102.8(3) . . ?
N2 C1 N1 103.2(3) . . ?
N2 C1 Au1 125.1(3) . . ?
N1 C1 Au1 131.7(3) . . ?
N3 C2 N1 111.6(4) . . ?
N1 C3 C4 113.9(3) . . ?
C9 C4 C5 118.4(4) . . ?
C9 C4 C3 122.6(4) . . ?
C5 C4 C3 118.9(4) . . ?
C6 C5 C4 121.1(4) . . ?
C7 C6 C5 120.2(4) . . ?
C6 C7 C8 119.9(4) . . ?
C9 C8 C7 119.3(4) . . ?
C4 C9 C8 121.0(4) . . ?
F2 P1 F2 180.00(15) . 3_566 ?
F2 P1 F3 89.71(13) . . ?
F2 P1 F3 90.29(13) 3_566 . ?
F2 P1 F3 90.29(13) . 3_566 ?
F2 P1 F3 89.71(13) 3_566 3_566 ?
F3 P1 F3 180.00(14) . 3_566 ?
F2 P1 F1 90.26(13) . . ?
F2 P1 F1 89.74(13) 3_566 . ?
F3 P1 F1 89.58(12) . . ?
F3 P1 F1 90.42(12) 3_566 . ?
F2 P1 F1 89.74(13) . 3_566 ?
F2 P1 F1 90.26(13) 3_566 3_566 ?
F3 P1 F1 90.42(12) . 3_566 ?
F3 P1 F1 89.58(12) 3_566 3_566 ?
F1 P1 F1 180.00(12) . 3_566 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         3.260
_refine_diff_density_min         -1.759
_refine_diff_density_rms         0.173
####################################################################### 
# 
# 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_c288
_audit_block_doi                 10.5517/cc13k6xs
_database_code_depnum_ccdc_archive 'CCDC 1029445'
_audit_update_record             
;
2014-12-05 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 Au I3 N3'
_chemical_formula_weight         750.88

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.6366(6)
_cell_length_b                   14.8770(11)
_cell_length_c                   12.5813(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.683(2)
_cell_angle_gamma                90.00
_cell_volume                     1605.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4663
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.38

_exptl_crystal_description       Block
_exptl_crystal_colour            'Dark Red'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      'Not measured'
_exptl_crystal_density_diffrn    3.106
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320
_exptl_absorpt_coefficient_mu    14.916
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.1948
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_process_details   
;
'SADABS v1.00 (Bruker,2008) was used for absorption correction. 
R(int) was 0.1197 before and 0.0531 after correction. The Ratio of 
minimum to maximum transmission is 0.4525. The l/2 correction factor 
is 0.0015'
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11014
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3671
_reflns_number_gt                3362
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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.

The benzene ring was disordered into two positions with occupancy 
ratio= 54: 46. Restraints in bond lengths((SADI of Shelxtl program )  
and thermal parameters(DELU, SIMU of Shelxtl program )  were applied to
the disordered atoms. 

;

_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)+(0.0509P)²+42.6196P] 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         3671
_refine_ls_number_parameters     210
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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 0.16673(4) 0.86828(2) 0.22239(3) 0.01898(13) Uani 1 1 d . . .
I1 I -0.13431(8) 0.89408(6) 0.21430(8) 0.0381(2) Uani 1 1 d . . .
I2 I 0.13993(10) 0.80093(6) 0.03140(8) 0.0405(2) Uani 1 1 d . . .
I3 I 0.46793(7) 0.83746(5) 0.25428(6) 0.02351(17) Uani 1 1 d . . .
N1 N 0.1874(11) 0.8856(6) 0.4619(8) 0.0248(19) Uani 1 1 d . . .
N2 N 0.1824(10) 1.0149(6) 0.3912(8) 0.026(2) Uani 1 1 d . B .
N3 N 0.1955(12) 0.9454(7) 0.5453(8) 0.033(2) Uani 1 1 d . . .
C1 C 0.1810(12) 0.9267(7) 0.3697(9) 0.024(2) Uani 1 1 d . . .
C2 C 0.1934(14) 1.0234(8) 0.4978(11) 0.034(3) Uani 1 1 d . . .
H2 H 0.1989 1.0794 0.5343 0.040 Uiso 1 1 calc R . .
C3 C 0.1855(16) 0.7888(8) 0.4813(11) 0.036(3) Uani 1 1 d . . .
H3A H 0.1424 0.7578 0.4158 0.055 Uiso 1 1 calc R . .
H3B H 0.1209 0.7760 0.5386 0.055 Uiso 1 1 calc R . .
H3C H 0.2921 0.7678 0.5027 0.055 Uiso 1 1 calc R . .
C4 C 0.1647(13) 1.0895(7) 0.3132(10) 0.028(2) Uani 1 1 d . . .
H4A H 0.1677 1.1473 0.3523 0.034 Uiso 1 1 calc R A 1
H4B H 0.0616 1.0846 0.2700 0.034 Uiso 1 1 calc R A 1
C5 C 0.297(3) 1.090(4) 0.2355(17) 0.025(4) Uani 0.54(6) 1 d PDU B 1
C6 C 0.278(3) 1.0785(18) 0.1246(17) 0.026(4) Uani 0.54(6) 1 d PDU B 1
H6 H 0.1774 1.0693 0.0875 0.031 Uiso 0.54(6) 1 calc PR B 1
C7 C 0.408(4) 1.0808(16) 0.0679(13) 0.026(4) Uani 0.54(6) 1 d PDU B 1
H7 H 0.3951 1.0736 -0.0077 0.031 Uiso 0.54(6) 1 calc PR B 1
C8 C 0.556(3) 1.0937(16) 0.1226(18) 0.026(4) Uani 0.54(6) 1 d PDU B 1
H8 H 0.6448 1.0945 0.0843 0.031 Uiso 0.54(6) 1 calc PR B 1
C9 C 0.575(3) 1.1054(18) 0.2334(19) 0.026(4) Uani 0.54(6) 1 d PDU B 1
H9 H 0.6759 1.1163 0.2702 0.031 Uiso 0.54(6) 1 calc PR B 1
C10 C 0.446(3) 1.101(3) 0.2899(15) 0.025(4) Uani 0.54(6) 1 d PDU B 1
H10 H 0.4588 1.1062 0.3657 0.030 Uiso 0.54(6) 1 calc PR B 1
C5A C 0.289(3) 1.090(4) 0.2481(19) 0.023(5) Uani 0.46(6) 1 d PDU B 2
C6A C 0.236(3) 1.0739(19) 0.1415(19) 0.023(5) Uani 0.46(6) 1 d PDU B 2
H6A H 0.1282 1.0653 0.1202 0.027 Uiso 0.46(6) 1 calc PR B 2
C7A C 0.341(4) 1.0701(17) 0.0662(16) 0.024(5) Uani 0.46(6) 1 d PDU B 2
H7A H 0.3053 1.0569 -0.0064 0.028 Uiso 0.46(6) 1 calc PR B 2
C8A C 0.498(4) 1.0854(16) 0.097(2) 0.024(5) Uani 0.46(6) 1 d PDU B 2
H8A H 0.5697 1.0844 0.0449 0.029 Uiso 0.46(6) 1 calc PR B 2
C9A C 0.551(3) 1.102(2) 0.203(2) 0.024(5) Uani 0.46(6) 1 d PDU B 2
H9A H 0.6593 1.1107 0.2246 0.029 Uiso 0.46(6) 1 calc PR B 2
C10A C 0.446(3) 1.107(3) 0.2783(18) 0.023(5) Uani 0.46(6) 1 d PDU B 2
H10A H 0.4814 1.1219 0.3505 0.028 Uiso 0.46(6) 1 calc PR B 2


_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 C1 2.038(11) . ?
Au1 I2 2.5888(10) . ?
Au1 I1 2.6183(8) . ?
Au1 I3 2.6259(7) . ?
N1 C1 1.306(15) . ?
N1 N3 1.371(13) . ?
N1 C3 1.461(15) . ?
N2 C2 1.339(16) . ?
N2 C1 1.339(14) . ?
N2 C4 1.477(15) . ?
N3 C2 1.305(17) . ?
C4 C5A 1.43(2) . ?
C4 C5 1.59(2) . ?
C5 C10 1.396(11) . ?
C5 C6 1.396(11) . ?
C6 C7 1.395(11) . ?
C7 C8 1.396(11) . ?
C8 C9 1.396(11) . ?
C9 C10 1.395(11) . ?
C5A C10A 1.386(12) . ?
C5A C6A 1.386(12) . ?
C6A C7A 1.386(12) . ?
C7A C8A 1.386(12) . ?
C8A C9A 1.386(12) . ?
C9A C10A 1.386(12) . ?

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
C1 Au1 I2 177.1(3) . . ?
C1 Au1 I1 85.8(3) . . ?
I2 Au1 I1 92.27(3) . . ?
C1 Au1 I3 88.9(3) . . ?
I2 Au1 I3 93.11(3) . . ?
I1 Au1 I3 173.26(3) . . ?
C1 N1 N3 111.7(10) . . ?
C1 N1 C3 127.6(10) . . ?
N3 N1 C3 120.7(10) . . ?
C2 N2 C1 107.0(10) . . ?
C2 N2 C4 125.8(10) . . ?
C1 N2 C4 127.1(10) . . ?
C2 N3 N1 103.2(10) . . ?
N1 C1 N2 106.3(10) . . ?
N1 C1 Au1 126.8(8) . . ?
N2 C1 Au1 126.9(9) . . ?
N3 C2 N2 111.8(10) . . ?
C5A C4 N2 111(2) . . ?
C5A C4 C5 3.0(16) . . ?
N2 C4 C5 113(2) . . ?
C10 C5 C6 119.7(14) . . ?
C10 C5 C4 112.7(17) . . ?
C6 C5 C4 127.6(17) . . ?
C7 C6 C5 120.3(14) . . ?
C6 C7 C8 119.7(14) . . ?
C9 C8 C7 120.3(14) . . ?
C10 C9 C8 119.7(14) . . ?
C9 C10 C5 120.3(14) . . ?
C10A C5A C6A 119.9(16) . . ?
C10A C5A C4 128(2) . . ?
C6A C5A C4 112(2) . . ?
C7A C6A C5A 120.1(16) . . ?
C8A C7A C6A 119.9(16) . . ?
C9A C8A C7A 120.1(16) . . ?
C8A C9A C10A 119.9(16) . . ?
C5A C10A C9A 120.1(17) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.602
_refine_diff_density_min         -3.524
_refine_diff_density_rms         0.313
