# 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_13mz146_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H7 Au Cl2 F N'
_chemical_formula_weight         440.04

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1445(19)
_cell_length_b                   7.8648(16)
_cell_length_c                   15.710(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.294(5)
_cell_angle_gamma                90
_cell_volume                     1084.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5931
_cell_measurement_theta_min      2.7070
_cell_measurement_theta_max      31.1682

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.695
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    14.037
_shelx_estimated_absorpt_T_min   0.102
_shelx_estimated_absorpt_T_max   0.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3172
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'Apex2 v2013.4-1 (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9330
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.921
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2685
_reflns_number_gt                2270
_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       'Apex2 v2013.4-1 (Bruker, 2012)'
_computing_cell_refinement       'SAINT V8.30C (Bruker, 2012)'
_computing_data_reduction        'SAINT V8.30C (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev609 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0566P)²] 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         2685
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.51946(3) 0.43739(3) 0.16561(2) 0.01035(10) Uani 1 1 d . . . . .
N1 N 0.6969(6) 0.3263(6) 0.1322(3) 0.0141(11) Uani 1 1 d . . . . .
C1 C 0.8418(7) 0.3273(8) 0.1830(4) 0.0170(13) Uani 1 1 d . . . . .
H1 H 0.8655 0.3780 0.2401 0.020 Uiso 1 1 calc R U . . .
F1 F 0.0359(4) 0.2765(5) -0.1109(3) 0.0258(9) Uani 1 1 d . . . . .
Cl4 Cl 0.6716(2) 0.55322(18) 0.30116(9) 0.0162(3) Uani 1 1 d . . . . .
C4 C 0.7715(7) 0.1810(8) 0.0178(4) 0.0153(12) Uani 1 1 d . . . . .
H4 H 0.7465 0.1311 -0.0395 0.018 Uiso 1 1 calc R U . . .
C3 C 0.9217(8) 0.1834(8) 0.0706(4) 0.0187(13) Uani 1 1 d . . . . .
H3 H 1.0002 0.1352 0.0495 0.022 Uiso 1 1 calc R U . . .
C2 C 0.9562(9) 0.2567(9) 0.1542(4) 0.0210(14) Uani 1 1 d . . . . .
H2 H 1.0582 0.2578 0.1911 0.025 Uiso 1 1 calc R U . . .
Cl5 Cl 0.3091(2) 0.55919(18) 0.18950(10) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.4974(7) 0.2560(7) 0.0036(3) 0.0123(13) Uani 1 1 d . . . . .
C7 C 0.4323(8) 0.1788(8) -0.0791(4) 0.0155(12) Uani 1 1 d . . . . .
H7 H 0.4954 0.1213 -0.1086 0.019 Uiso 1 1 calc R U . . .
C8 C 0.2764(7) 0.1863(8) -0.1176(4) 0.0153(12) Uani 1 1 d . . . . .
H8 H 0.2314 0.1340 -0.1734 0.018 Uiso 1 1 calc R U . . .
C9 C 0.1885(8) 0.2710(8) -0.0734(4) 0.0171(13) Uani 1 1 d . . . . .
C10 C 0.2460(8) 0.3490(7) 0.0088(4) 0.0149(13) Uani 1 1 d . . . . .
H10 H 0.1813 0.4062 0.0373 0.018 Uiso 1 1 calc R U . . .
C11 C 0.4015(7) 0.3392(7) 0.0470(3) 0.0106(11) Uani 1 1 d . . . . .
C5 C 0.6595(7) 0.2519(7) 0.0497(4) 0.0112(12) 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 C11 2.026(5) . ?
Au1 N1 2.038(5) . ?
Au1 Cl5 2.2722(17) . ?
Au1 Cl4 2.3744(15) . ?
N1 C1 1.342(8) . ?
N1 C5 1.374(7) . ?
C1 C2 1.369(9) . ?
C1 H1 0.9500 . ?
F1 C9 1.354(8) . ?
C4 C5 1.378(9) . ?
C4 C3 1.391(9) . ?
C4 H4 0.9500 . ?
C3 C2 1.388(9) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C6 C7 1.406(8) . ?
C6 C11 1.413(8) . ?
C6 C5 1.457(9) . ?
C7 C8 1.384(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(8) . ?
C10 C11 1.382(9) . ?
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
C11 Au1 N1 81.7(2) . . ?
C11 Au1 Cl5 93.19(18) . . ?
N1 Au1 Cl5 174.70(14) . . ?
C11 Au1 Cl4 176.33(17) . . ?
N1 Au1 Cl4 94.99(15) . . ?
Cl5 Au1 Cl4 90.02(6) . . ?
C1 N1 C5 120.5(5) . . ?
C1 N1 Au1 124.7(4) . . ?
C5 N1 Au1 114.8(4) . . ?
N1 C1 C2 121.3(6) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C1 C2 C3 119.3(7) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C7 C6 C11 119.1(6) . . ?
C7 C6 C5 123.9(5) . . ?
C11 C6 C5 116.9(5) . . ?
C8 C7 C6 120.2(6) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 118.5(5) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
F1 C9 C8 118.3(5) . . ?
F1 C9 C10 117.7(6) . . ?
C8 C9 C10 124.1(6) . . ?
C11 C10 C9 117.0(6) . . ?
C11 C10 H10 121.5 . . ?
C9 C10 H10 121.5 . . ?
C10 C11 C6 121.2(5) . . ?
C10 C11 Au1 126.6(4) . . ?
C6 C11 Au1 112.2(4) . . ?
N1 C5 C4 120.1(6) . . ?
N1 C5 C6 114.2(5) . . ?
C4 C5 C6 125.8(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
C5 N1 C1 C2 0.8(9) . . . . ?
Au1 N1 C1 C2 -176.9(5) . . . . ?
C5 C4 C3 C2 0.1(9) . . . . ?
N1 C1 C2 C3 0.3(10) . . . . ?
C4 C3 C2 C1 -0.8(10) . . . . ?
C11 C6 C7 C8 0.7(8) . . . . ?
C5 C6 C7 C8 178.9(6) . . . . ?
C6 C7 C8 C9 0.3(9) . . . . ?
C7 C8 C9 F1 -179.3(5) . . . . ?
C7 C8 C9 C10 -0.8(10) . . . . ?
F1 C9 C10 C11 178.7(5) . . . . ?
C8 C9 C10 C11 0.1(9) . . . . ?
C9 C10 C11 C6 1.0(8) . . . . ?
C9 C10 C11 Au1 -179.6(4) . . . . ?
C7 C6 C11 C10 -1.4(8) . . . . ?
C5 C6 C11 C10 -179.7(5) . . . . ?
C7 C6 C11 Au1 179.1(4) . . . . ?
C5 C6 C11 Au1 0.8(6) . . . . ?
C1 N1 C5 C4 -1.5(8) . . . . ?
Au1 N1 C5 C4 176.4(4) . . . . ?
C1 N1 C5 C6 178.1(5) . . . . ?
Au1 N1 C5 C6 -4.0(6) . . . . ?
C3 C4 C5 N1 1.0(9) . . . . ?
C3 C4 C5 C6 -178.5(6) . . . . ?
C7 C6 C5 N1 -176.1(5) . . . . ?
C11 C6 C5 N1 2.1(7) . . . . ?
C7 C6 C5 C4 3.5(9) . . . . ?
C11 C6 C5 C4 -178.4(5) . . . . ?

_refine_diff_density_max         2.826
_refine_diff_density_min         -2.095
_refine_diff_density_rms         0.305

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1009034'
#######################################################################
#
#                 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_13mz182_0m

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Au F2 N'
_chemical_formula_weight         555.36

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'
Au Au -2.0133 8.8022 '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'

_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                   14.8527(13)
_cell_length_b                   16.3867(14)
_cell_length_c                   17.6200(15)
_cell_angle_alpha                90.1560(10)
_cell_angle_beta                 91.4140(10)
_cell_angle_gamma                114.2560(10)
_cell_volume                     3908.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.4102
_cell_measurement_theta_max      30.7963

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_F_000             2128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    7.555
_shelx_estimated_absorpt_T_min   0.397
_shelx_estimated_absorpt_T_max   0.660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4870
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'Apex2 v2013.4-1 (Bruker, 2013)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69608
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.156
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             15989
_reflns_number_gt                13562
_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. These statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Apex2 v2013.4-1 (Bruker, 2013)'
_computing_cell_refinement       'SAINT V8.30C (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev645 (Hübschle et al., 2011)
;
_computing_molecular_graphics    'Shelxtl (Bruker, 2003)'
_computing_publication_material  'Shelxtl (Bruker, 2003)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0398P)²+11.0694P]
 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         15989
_refine_ls_number_parameters     1014
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
C1 C 0.8337(4) 0.7758(4) -0.0391(3) 0.0244(12) Uani 1 1 d . . . . .
H1 H 0.7642 0.7574 -0.0439 0.029 Uiso 1 1 calc R U . . .
C2 C 0.8786(5) 0.7343(4) -0.0842(3) 0.0271(13) Uani 1 1 d . . . . .
H2 H 0.8407 0.6880 -0.1192 0.033 Uiso 1 1 calc R U . . .
C3 C 0.9791(5) 0.7620(4) -0.0768(3) 0.0289(13) Uani 1 1 d . . . . .
H3 H 1.0117 0.7352 -0.1072 0.035 Uiso 1 1 calc R U . . .
C4 C 1.0327(5) 0.8291(4) -0.0251(3) 0.0287(13) Uani 1 1 d . . . . .
H4 H 1.1022 0.8479 -0.0193 0.034 Uiso 1 1 calc R U . . .
C5 C 0.9840(4) 0.8691(4) 0.0187(3) 0.0211(11) Uani 1 1 d . . . . .
C6 C 1.0320(4) 0.9404(4) 0.0751(3) 0.0208(11) Uani 1 1 d . . . . .
C7 C 1.1344(4) 0.9795(4) 0.0886(3) 0.0252(12) Uani 1 1 d . . . . .
H7 H 1.1755 0.9600 0.0601 0.030 Uiso 1 1 calc R U . . .
C8 C 1.1761(4) 1.0462(4) 0.1429(3) 0.0267(13) Uani 1 1 d . . . . .
H8 H 1.2458 1.0723 0.1511 0.032 Uiso 1 1 calc R U . . .
C9 C 1.1179(4) 1.0762(4) 0.1861(3) 0.0287(13) Uani 1 1 d . . . . .
C10 C 1.0160(4) 1.0374(4) 0.1707(3) 0.0246(12) Uani 1 1 d . . . . .
H10 H 0.9755 1.0581 0.1988 0.029 Uiso 1 1 calc R U . . .
C11 C 0.9708(4) 0.9704(4) 0.1167(3) 0.0204(11) Uani 1 1 d . . . . .
C12 C 1.1622(5) 1.1472(4) 0.2467(4) 0.0360(15) Uani 1 1 d . . . . .
H12A H 1.1633 1.2040 0.2284 0.054 Uiso 1 1 calc R U . . .
H12B H 1.2299 1.1545 0.2591 0.054 Uiso 1 1 calc R U . . .
H12C H 1.1225 1.1294 0.2923 0.054 Uiso 1 1 calc R U . . .
C13 C 0.7792(4) 0.9722(4) 0.1598(3) 0.0221(12) Uani 1 1 d . . . . .
C14 C 0.7473(4) 1.0377(4) 0.1387(3) 0.0250(12) Uani 1 1 d . . . . .
H14 H 0.7440 1.0504 0.0863 0.030 Uiso 1 1 calc R U . . .
C15 C 0.7201(5) 1.0851(4) 0.1921(4) 0.0321(14) Uani 1 1 d . . . . .
H15 H 0.6991 1.1302 0.1768 0.038 Uiso 1 1 calc R U . . .
C16 C 0.7241(5) 1.0657(4) 0.2670(4) 0.0338(15) Uani 1 1 d . . . . .
C17 C 0.7528(5) 0.9999(4) 0.2913(3) 0.0314(14) Uani 1 1 d . . . . .
H17 H 0.7537 0.9868 0.3438 0.038 Uiso 1 1 calc R U . . .
C18 C 0.7800(4) 0.9536(4) 0.2379(3) 0.0271(13) Uani 1 1 d . . . . .
H18 H 0.7998 0.9080 0.2540 0.033 Uiso 1 1 calc R U . . .
C19 C 0.6800(4) 0.8363(4) 0.0475(3) 0.0198(11) Uani 1 1 d . . . . .
C20 C 0.6269(4) 0.8706(4) 0.0010(3) 0.0221(12) Uani 1 1 d . . . . .
H20 H 0.6566 0.9321 -0.0122 0.026 Uiso 1 1 calc R U . . .
C21 C 0.5327(4) 0.8183(4) -0.0266(3) 0.0219(12) Uani 1 1 d . . . . .
H21 H 0.4985 0.8431 -0.0588 0.026 Uiso 1 1 calc R U . . .
C22 C 0.4892(4) 0.7298(4) -0.0066(3) 0.0226(12) Uani 1 1 d . . . . .
C23 C 0.5362(4) 0.6921(4) 0.0395(3) 0.0257(12) Uani 1 1 d . . . . .
H23 H 0.5052 0.6307 0.0526 0.031 Uiso 1 1 calc R U . . .
C24 C 0.6308(4) 0.7461(4) 0.0668(3) 0.0218(12) Uani 1 1 d . . . . .
H24 H 0.6635 0.7207 0.0999 0.026 Uiso 1 1 calc R U . . .
C25 C 0.2676(4) 0.3080(4) 0.5575(3) 0.0224(12) Uani 1 1 d . . . . .
H25 H 0.2637 0.2489 0.5617 0.027 Uiso 1 1 calc R U . . .
C26 C 0.2119(4) 0.3350(4) 0.6048(3) 0.0268(13) Uani 1 1 d . . . . .
H26 H 0.1700 0.2953 0.6407 0.032 Uiso 1 1 calc R U . . .
C27 C 0.2187(4) 0.4208(4) 0.5985(3) 0.0296(13) Uani 1 1 d . . . . .
H27 H 0.1805 0.4407 0.6299 0.035 Uiso 1 1 calc R U . . .
C28 C 0.2810(4) 0.4781(4) 0.5466(3) 0.0265(13) Uani 1 1 d . . . . .
H28 H 0.2866 0.5378 0.5430 0.032 Uiso 1 1 calc R U . . .
C29 C 0.3357(4) 0.4483(3) 0.4993(3) 0.0187(11) Uani 1 1 d . . . . .
C30 C 0.4027(4) 0.5017(3) 0.4411(3) 0.0180(11) Uani 1 1 d . . . . .
C31 C 0.4207(4) 0.5912(3) 0.4279(3) 0.0202(11) Uani 1 1 d . . . . .
H31 H 0.3899 0.6200 0.4580 0.024 Uiso 1 1 calc R U . . .
C32 C 0.4838(4) 0.6380(4) 0.3707(3) 0.0232(12) Uani 1 1 d . . . . .
H32 H 0.4959 0.6988 0.3621 0.028 Uiso 1 1 calc R U . . .
C33 C 0.5289(4) 0.5966(4) 0.3261(3) 0.0202(11) Uani 1 1 d . . . . .
C34 C 0.5113(4) 0.5079(3) 0.3406(3) 0.0205(11) Uani 1 1 d . . . . .
H34 H 0.5433 0.4799 0.3109 0.025 Uiso 1 1 calc R U . . .
C35 C 0.4488(4) 0.4588(3) 0.3971(3) 0.0170(11) Uani 1 1 d . . . . .
C36 C 0.5934(5) 0.6463(4) 0.2619(3) 0.0312(14) Uani 1 1 d . . . . .
H36A H 0.5554 0.6291 0.2138 0.047 Uiso 1 1 calc R U . . .
H36B H 0.6506 0.6313 0.2598 0.047 Uiso 1 1 calc R U . . .
H36C H 0.6160 0.7109 0.2705 0.047 Uiso 1 1 calc R U . . .
C37 C 0.4949(4) 0.3059(3) 0.3490(3) 0.0189(11) Uani 1 1 d . . . . .
C38 C 0.5809(4) 0.2960(4) 0.3671(3) 0.0240(12) Uani 1 1 d . . . . .
H38 H 0.6006 0.2973 0.4189 0.029 Uiso 1 1 calc R U . . .
C39 C 0.6396(5) 0.2840(4) 0.3107(3) 0.0282(13) Uani 1 1 d . . . . .
H39 H 0.6989 0.2777 0.3234 0.034 Uiso 1 1 calc R U . . .
C40 C 0.6087(5) 0.2819(4) 0.2372(3) 0.0293(14) Uani 1 1 d . . . . .
C41 C 0.5244(5) 0.2906(4) 0.2159(3) 0.0299(14) Uani 1 1 d . . . . .
H41 H 0.5051 0.2882 0.1638 0.036 Uiso 1 1 calc R U . . .
C42 C 0.4668(4) 0.3032(4) 0.2727(3) 0.0233(12) Uani 1 1 d . . . . .
H42 H 0.4080 0.3099 0.2590 0.028 Uiso 1 1 calc R U . . .
C43 C 0.3688(4) 0.1966(3) 0.4615(3) 0.0188(11) Uani 1 1 d . . . . .
C44 C 0.4311(4) 0.1621(4) 0.4959(3) 0.0244(12) Uani 1 1 d . . . . .
H44 H 0.4983 0.2013 0.5058 0.029 Uiso 1 1 calc R U . . .
C45 C 0.3992(5) 0.0723(4) 0.5166(3) 0.0281(13) Uani 1 1 d . . . . .
H45 H 0.4429 0.0506 0.5405 0.034 Uiso 1 1 calc R U . . .
C46 C 0.3021(5) 0.0169(4) 0.5008(3) 0.0285(14) Uani 1 1 d . . . . .
C47 C 0.2369(4) 0.0458(4) 0.4680(3) 0.0261(13) Uani 1 1 d . . . . .
H47 H 0.1699 0.0057 0.4585 0.031 Uiso 1 1 calc R U . . .
C48 C 0.2706(4) 0.1354(4) 0.4488(3) 0.0241(12) Uani 1 1 d . . . . .
H48 H 0.2253 0.1561 0.4261 0.029 Uiso 1 1 calc R U . . .
C49 C 0.3992(4) 0.7235(4) 0.1897(3) 0.0256(12) Uani 1 1 d . . . . .
H49 H 0.3887 0.6830 0.1483 0.031 Uiso 1 1 calc R U . . .
C50 C 0.4750(4) 0.8074(4) 0.1865(3) 0.0244(12) Uani 1 1 d . . . . .
H50 H 0.5157 0.8249 0.1435 0.029 Uiso 1 1 calc R U . . .
C51 C 0.4908(4) 0.8655(4) 0.2471(3) 0.0259(12) Uani 1 1 d . . . . .
H51 H 0.5443 0.9229 0.2474 0.031 Uiso 1 1 calc R U . . .
C52 C 0.4279(4) 0.8394(4) 0.3071(3) 0.0229(12) Uani 1 1 d . . . . .
H52 H 0.4365 0.8799 0.3481 0.027 Uiso 1 1 calc R U . . .
C53 C 0.3523(4) 0.7541(4) 0.3082(3) 0.0215(11) Uani 1 1 d . . . . .
C54 C 0.2856(4) 0.7164(3) 0.3712(3) 0.0192(11) Uani 1 1 d . . . . .
C55 C 0.2902(4) 0.7651(4) 0.4377(3) 0.0225(12) Uani 1 1 d . . . . .
H55 H 0.3343 0.8265 0.4416 0.027 Uiso 1 1 calc R U . . .
C56 C 0.2308(4) 0.7239(4) 0.4979(3) 0.0208(11) Uani 1 1 d . . . . .
H56 H 0.2349 0.7575 0.5429 0.025 Uiso 1 1 calc R U . . .
C57 C 0.1657(4) 0.6350(4) 0.4939(3) 0.0249(12) Uani 1 1 d . . . . .
C58 C 0.1605(4) 0.5874(4) 0.4258(3) 0.0233(12) Uani 1 1 d . . . . .
H58 H 0.1154 0.5263 0.4220 0.028 Uiso 1 1 calc R U . . .
C59 C 0.2185(4) 0.6260(4) 0.3645(3) 0.0210(11) Uani 1 1 d . . . . .
C60 C 0.1029(5) 0.5911(4) 0.5605(3) 0.0354(15) Uani 1 1 d . . . . .
H60A H 0.0458 0.6066 0.5612 0.053 Uiso 1 1 calc R U . . .
H60B H 0.1421 0.6121 0.6077 0.053 Uiso 1 1 calc R U . . .
H60C H 0.0798 0.5259 0.5559 0.053 Uiso 1 1 calc R U . . .
C61 C 0.1347(4) 0.4406(4) 0.2876(3) 0.0239(12) Uani 1 1 d . . . . .
C62 C 0.0424(4) 0.4040(4) 0.2505(3) 0.0276(13) Uani 1 1 d . . . . .
H62 H 0.0259 0.4380 0.2135 0.033 Uiso 1 1 calc R U . . .
C63 C -0.0250(4) 0.3190(4) 0.2671(4) 0.0336(15) Uani 1 1 d . . . . .
H63 H -0.0883 0.2947 0.2425 0.040 Uiso 1 1 calc R U . . .
C64 C 0.0002(5) 0.2699(4) 0.3194(3) 0.0324(15) Uani 1 1 d . . . . .
C65 C 0.0910(5) 0.3026(4) 0.3558(3) 0.0336(14) Uani 1 1 d . . . . .
H65 H 0.1077 0.2671 0.3911 0.040 Uiso 1 1 calc R U . . .
C66 C 0.1578(4) 0.3890(4) 0.3400(3) 0.0288(13) Uani 1 1 d . . . . .
H66 H 0.2205 0.4131 0.3655 0.035 Uiso 1 1 calc R U . . .
C67 C 0.2677(4) 0.5126(3) 0.1694(3) 0.0207(11) Uani 1 1 d . . . . .
C68 C 0.2284(4) 0.5182(4) 0.0977(3) 0.0255(12) Uani 1 1 d . . . . .
H68 H 0.1773 0.5389 0.0938 0.031 Uiso 1 1 calc R U . . .
C69 C 0.2619(4) 0.4944(4) 0.0322(3) 0.0268(13) Uani 1 1 d . . . . .
H69 H 0.2348 0.4993 -0.0161 0.032 Uiso 1 1 calc R U . . .
C70 C 0.3344(4) 0.4637(4) 0.0381(3) 0.0269(13) Uani 1 1 d . . . . .
C71 C 0.3731(4) 0.4527(4) 0.1075(3) 0.0265(13) Uani 1 1 d . . . . .
H71 H 0.4220 0.4294 0.1106 0.032 Uiso 1 1 calc R U . . .
C72 C 0.3382(4) 0.4770(4) 0.1729(3) 0.0250(12) Uani 1 1 d . . . . .
H72 H 0.3633 0.4690 0.2211 0.030 Uiso 1 1 calc R U . . .
C73 C 0.2775(4) 0.9631(4) 0.2924(3) 0.0256(12) Uani 1 1 d . . . . .
H73 H 0.2368 0.9545 0.3350 0.031 Uiso 1 1 calc R U . . .
C74 C 0.3678(5) 1.0370(4) 0.2917(4) 0.0324(14) Uani 1 1 d . . . . .
H74 H 0.3889 1.0787 0.3329 0.039 Uiso 1 1 calc R U . . .
C75 C 0.4260(5) 1.0483(4) 0.2289(4) 0.0335(15) Uani 1 1 d . . . . .
H75 H 0.4879 1.0983 0.2262 0.040 Uiso 1 1 calc R U . . .
C76 C 0.3929(5) 0.9860(4) 0.1703(4) 0.0320(14) Uani 1 1 d . . . . .
H76 H 0.4329 0.9934 0.1274 0.038 Uiso 1 1 calc R U . . .
C77 C 0.3024(4) 0.9128(4) 0.1728(3) 0.0233(12) Uani 1 1 d . . . . .
C78 C 0.2604(4) 0.8421(4) 0.1150(3) 0.0239(12) Uani 1 1 d . . . . .
C79 C 0.3062(5) 0.8427(5) 0.0469(3) 0.0332(15) Uani 1 1 d . . . . .
H79 H 0.3671 0.8912 0.0362 0.040 Uiso 1 1 calc R U . . .
C80 C 0.2642(5) 0.7735(5) -0.0053(3) 0.0365(16) Uani 1 1 d . . . . .
H80 H 0.2975 0.7743 -0.0508 0.044 Uiso 1 1 calc R U . . .
C81 C 0.1741(5) 0.7027(4) 0.0076(3) 0.0330(15) Uani 1 1 d . . . . .
C82 C 0.1278(5) 0.7029(4) 0.0758(3) 0.0298(14) Uani 1 1 d . . . . .
H82 H 0.0663 0.6548 0.0856 0.036 Uiso 1 1 calc R U . . .
C83 C 0.1692(4) 0.7717(4) 0.1298(3) 0.0244(12) Uani 1 1 d . . . . .
C84 C 0.1295(6) 0.6288(5) -0.0496(4) 0.048(2) Uani 1 1 d . . . . .
H84A H 0.1040 0.6502 -0.0935 0.072 Uiso 1 1 calc R U . . .
H84B H 0.0753 0.5785 -0.0268 0.072 Uiso 1 1 calc R U . . .
H84C H 0.1800 0.6090 -0.0661 0.072 Uiso 1 1 calc R U . . .
C85 C -0.0213(4) 0.6856(3) 0.2129(3) 0.0202(11) Uani 1 1 d . . . . .
C86 C -0.0343(4) 0.6006(4) 0.2370(3) 0.0258(12) Uani 1 1 d . . . . .
H86 H 0.0179 0.5930 0.2640 0.031 Uiso 1 1 calc R U . . .
C87 C -0.1223(5) 0.5271(4) 0.2222(3) 0.0314(14) Uani 1 1 d . . . . .
H87 H -0.1304 0.4692 0.2381 0.038 Uiso 1 1 calc R U . . .
C88 C -0.1970(4) 0.5389(4) 0.1846(3) 0.0313(14) Uani 1 1 d . . . . .
C89 C -0.1880(5) 0.6219(4) 0.1606(3) 0.0316(14) Uani 1 1 d . . . . .
H89 H -0.2413 0.6286 0.1348 0.038 Uiso 1 1 calc R U . . .
C90 C -0.0995(4) 0.6952(4) 0.1750(3) 0.0270(13) Uani 1 1 d . . . . .
H90 H -0.0921 0.7527 0.1587 0.032 Uiso 1 1 calc R U . . .
C91 C 0.0513(4) 0.8206(3) 0.3262(3) 0.0183(11) Uani 1 1 d . . . . .
C92 C 0.0065(4) 0.8803(4) 0.3265(3) 0.0247(12) Uani 1 1 d . . . . .
H92 H -0.0011 0.9066 0.2801 0.030 Uiso 1 1 calc R U . . .
C93 C -0.0273(4) 0.9026(3) 0.3928(3) 0.0232(12) Uani 1 1 d . . . . .
H93 H -0.0583 0.9431 0.3921 0.028 Uiso 1 1 calc R U . . .
C94 C -0.0151(4) 0.8647(4) 0.4593(3) 0.0232(12) Uani 1 1 d . . . . .
C95 C 0.0291(4) 0.8059(4) 0.4625(3) 0.0253(12) Uani 1 1 d . . . . .
H95 H 0.0377 0.7814 0.5094 0.030 Uiso 1 1 calc R U . . .
C96 C 0.0610(4) 0.7830(4) 0.3953(3) 0.0246(12) Uani 1 1 d . . . . .
H96 H 0.0900 0.7410 0.3965 0.029 Uiso 1 1 calc R U . . .
N1 N 0.8849(3) 0.8405(3) 0.0105(3) 0.0208(10) Uani 1 1 d . . . . .
N2 N 0.3272(3) 0.3627(3) 0.5058(2) 0.0185(9) Uani 1 1 d . . . . .
N3 N 0.3401(3) 0.6968(3) 0.2485(3) 0.0209(10) Uani 1 1 d . . . . .
N4 N 0.2460(3) 0.9032(3) 0.2347(3) 0.0210(10) Uani 1 1 d . . . . .
F1 F 0.6960(3) 1.1111(3) 0.3195(2) 0.0519(11) Uani 1 1 d . . . . .
F2 F 0.3969(2) 0.6779(2) -0.03514(19) 0.0325(8) Uani 1 1 d . . . . .
F3 F 0.6651(3) 0.2689(3) 0.1816(2) 0.0460(10) Uani 1 1 d . . . . .
F4 F 0.2699(3) -0.0711(2) 0.5201(2) 0.0416(9) Uani 1 1 d . . . . .
F5 F -0.0651(3) 0.1854(3) 0.3353(2) 0.0534(12) Uani 1 1 d . . . . .
F6 F 0.3697(3) 0.4430(3) -0.02625(19) 0.0384(9) Uani 1 1 d . . . . .
F7 F -0.2841(3) 0.4671(3) 0.1697(2) 0.0472(10) Uani 1 1 d . . . . .
F8 F -0.0458(3) 0.8875(2) 0.52550(19) 0.0339(8) Uani 1 1 d . . . . .
Au1 Au 0.82455(2) 0.90651(2) 0.08431(2) 0.01792(5) Uani 1 1 d . . . . .
Au2 Au 0.41282(2) 0.32802(2) 0.42850(2) 0.01518(5) Uani 1 1 d . . . . .
Au3 Au 0.23446(2) 0.56506(2) 0.26583(2) 0.01863(5) Uani 1 1 d . . . . .
Au4 Au 0.10761(2) 0.79200(2) 0.22822(2) 0.01759(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
C1 N1 1.328(7) . ?
C1 C2 1.392(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.373(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(8) . ?
C4 H4 0.9500 . ?
C5 N1 1.353(7) . ?
C5 C6 1.461(8) . ?
C6 C7 1.400(8) . ?
C6 C11 1.416(7) . ?
C7 C8 1.380(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(8) . ?
C9 C12 1.503(9) . ?
C10 C11 1.385(8) . ?
C10 H10 0.9500 . ?
C11 Au1 2.052(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.387(8) . ?
C13 C18 1.412(8) . ?
C13 Au1 2.004(5) . ?
C14 C15 1.389(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.364(9) . ?
C15 H15 0.9500 . ?
C16 F1 1.360(7) . ?
C16 C17 1.379(9) . ?
C17 C18 1.376(8) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.395(7) . ?
C19 C24 1.400(7) . ?
C19 Au1 2.063(5) . ?
C20 C21 1.381(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.363(8) . ?
C22 F2 1.364(6) . ?
C23 C24 1.390(8) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 N2 1.346(7) . ?
C25 C26 1.380(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.371(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.381(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.396(8) . ?
C28 H28 0.9500 . ?
C29 N2 1.360(7) . ?
C29 C30 1.465(7) . ?
C30 C31 1.400(7) . ?
C30 C35 1.408(7) . ?
C31 C32 1.395(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.386(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.394(7) . ?
C33 C36 1.509(8) . ?
C34 C35 1.391(7) . ?
C34 H34 0.9500 . ?
C35 Au2 2.065(5) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.382(8) . ?
C37 C42 1.393(7) . ?
C37 Au2 2.006(5) . ?
C38 C39 1.404(8) . ?
C38 H38 0.9500 . ?
C39 C40 1.358(9) . ?
C39 H39 0.9500 . ?
C40 C41 1.361(9) . ?
C40 F3 1.377(6) . ?
C41 C42 1.401(8) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.396(8) . ?
C43 C48 1.401(8) . ?
C43 Au2 2.067(5) . ?
C44 C45 1.400(8) . ?
C44 H44 0.9500 . ?
C45 C46 1.372(9) . ?
C45 H45 0.9500 . ?
C46 C47 1.360(9) . ?
C46 F4 1.367(6) . ?
C47 C48 1.390(8) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 N3 1.330(7) . ?
C49 C50 1.376(8) . ?
C49 H49 0.9500 . ?
C50 C51 1.377(8) . ?
C50 H50 0.9500 . ?
C51 C52 1.377(8) . ?
C51 H51 0.9500 . ?
C52 C53 1.388(8) . ?
C52 H52 0.9500 . ?
C53 N3 1.366(7) . ?
C53 C54 1.467(8) . ?
C54 C55 1.400(7) . ?
C54 C59 1.407(7) . ?
C55 C56 1.386(8) . ?
C55 H55 0.9500 . ?
C56 C57 1.379(8) . ?
C56 H56 0.9500 . ?
C57 C58 1.411(8) . ?
C57 C60 1.508(8) . ?
C58 C59 1.383(8) . ?
C58 H58 0.9500 . ?
C59 Au3 2.069(5) . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C61 C66 1.382(8) . ?
C61 C62 1.394(8) . ?
C61 Au3 2.012(5) . ?
C62 C63 1.379(9) . ?
C62 H62 0.9500 . ?
C63 C64 1.367(9) . ?
C63 H63 0.9500 . ?
C64 F5 1.360(7) . ?
C64 C65 1.371(9) . ?
C65 C66 1.389(8) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C67 C72 1.393(8) . ?
C67 C68 1.398(8) . ?
C67 Au3 2.062(5) . ?
C68 C69 1.384(8) . ?
C68 H68 0.9500 . ?
C69 C70 1.365(8) . ?
C69 H69 0.9500 . ?
C70 F6 1.361(6) . ?
C70 C71 1.382(8) . ?
C71 C72 1.397(8) . ?
C71 H71 0.9500 . ?
C72 H72 0.9500 . ?
C73 N4 1.345(7) . ?
C73 C74 1.390(8) . ?
C73 H73 0.9500 . ?
C74 C75 1.387(9) . ?
C74 H74 0.9500 . ?
C75 C76 1.379(9) . ?
C75 H75 0.9500 . ?
C76 C77 1.388(8) . ?
C76 H76 0.9500 . ?
C77 N4 1.361(7) . ?
C77 C78 1.462(8) . ?
C78 C79 1.393(8) . ?
C78 C83 1.403(8) . ?
C79 C80 1.380(9) . ?
C79 H79 0.9500 . ?
C80 C81 1.389(10) . ?
C80 H80 0.9500 . ?
C81 C82 1.400(8) . ?
C81 C84 1.491(9) . ?
C82 C83 1.397(8) . ?
C82 H82 0.9500 . ?
C83 Au4 2.069(5) . ?
C84 H84A 0.9800 . ?
C84 H84B 0.9800 . ?
C84 H84C 0.9800 . ?
C85 C90 1.390(8) . ?
C85 C86 1.394(8) . ?
C85 Au4 2.002(5) . ?
C86 C87 1.383(8) . ?
C86 H86 0.9500 . ?
C87 C88 1.361(9) . ?
C87 H87 0.9500 . ?
C88 F7 1.362(7) . ?
C88 C89 1.378(9) . ?
C89 C90 1.385(8) . ?
C89 H89 0.9500 . ?
C90 H90 0.9500 . ?
C91 C92 1.391(8) . ?
C91 C96 1.397(7) . ?
C91 Au4 2.070(5) . ?
C92 C93 1.389(8) . ?
C92 H92 0.9500 . ?
C93 C94 1.371(8) . ?
C93 H93 0.9500 . ?
C94 F8 1.368(6) . ?
C94 C95 1.371(8) . ?
C95 C96 1.392(8) . ?
C95 H95 0.9500 . ?
C96 H96 0.9500 . ?
N1 Au1 2.124(4) . ?
N2 Au2 2.114(4) . ?
N3 Au3 2.112(4) . ?
N4 Au4 2.114(4) . ?

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 122.1(5) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 118.2(6) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 120.0(5) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 119.6(6) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 119.4(5) . . ?
N1 C5 C6 115.7(5) . . ?
C4 C5 C6 124.9(5) . . ?
C7 C6 C11 119.7(5) . . ?
C7 C6 C5 122.8(5) . . ?
C11 C6 C5 117.4(5) . . ?
C8 C7 C6 120.6(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.2(5) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 117.3(6) . . ?
C8 C9 C12 121.7(5) . . ?
C10 C9 C12 121.1(6) . . ?
C11 C10 C9 123.5(5) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C10 C11 C6 117.6(5) . . ?
C10 C11 Au1 129.7(4) . . ?
C6 C11 Au1 112.7(4) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 117.4(5) . . ?
C14 C13 Au1 122.4(4) . . ?
C18 C13 Au1 120.2(4) . . ?
C13 C14 C15 121.6(6) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 118.7(6) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 F1 118.9(6) . . ?
C15 C16 C17 122.3(6) . . ?
F1 C16 C17 118.8(6) . . ?
C18 C17 C16 118.5(6) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C17 C18 C13 121.5(6) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C20 C19 C24 116.0(5) . . ?
C20 C19 Au1 124.8(4) . . ?
C24 C19 Au1 119.1(4) . . ?
C21 C20 C19 122.1(5) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C22 C21 C20 119.0(5) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C23 C22 F2 119.2(5) . . ?
C23 C22 C21 122.0(5) . . ?
F2 C22 C21 118.8(5) . . ?
C22 C23 C24 118.0(5) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C23 C24 C19 122.8(5) . . ?
C23 C24 H24 118.6 . . ?
C19 C24 H24 118.6 . . ?
N2 C25 C26 122.2(5) . . ?
N2 C25 H25 118.9 . . ?
C26 C25 H25 118.9 . . ?
C27 C26 C25 118.3(5) . . ?
C27 C26 H26 120.9 . . ?
C25 C26 H26 120.9 . . ?
C26 C27 C28 120.1(5) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C29 120.0(5) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
N2 C29 C28 119.1(5) . . ?
N2 C29 C30 115.6(5) . . ?
C28 C29 C30 125.4(5) . . ?
C31 C30 C35 120.2(5) . . ?
C31 C30 C29 122.7(5) . . ?
C35 C30 C29 117.1(5) . . ?
C32 C31 C30 120.1(5) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C33 C32 C31 120.6(5) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 118.6(5) . . ?
C32 C33 C36 120.4(5) . . ?
C34 C33 C36 121.0(5) . . ?
C35 C34 C33 122.5(5) . . ?
C35 C34 H34 118.7 . . ?
C33 C34 H34 118.7 . . ?
C34 C35 C30 118.0(5) . . ?
C34 C35 Au2 129.0(4) . . ?
C30 C35 Au2 113.0(4) . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 C42 118.4(5) . . ?
C38 C37 Au2 122.1(4) . . ?
C42 C37 Au2 119.5(4) . . ?
C37 C38 C39 121.5(5) . . ?
C37 C38 H38 119.2 . . ?
C39 C38 H38 119.2 . . ?
C40 C39 C38 117.6(6) . . ?
C40 C39 H39 121.2 . . ?
C38 C39 H39 121.2 . . ?
C41 C40 C39 123.6(5) . . ?
C41 C40 F3 118.4(5) . . ?
C39 C40 F3 118.0(6) . . ?
C40 C41 C42 118.2(5) . . ?
C40 C41 H41 120.9 . . ?
C42 C41 H41 120.9 . . ?
C37 C42 C41 120.7(5) . . ?
C37 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C44 C43 C48 115.7(5) . . ?
C44 C43 Au2 124.5(4) . . ?
C48 C43 Au2 119.8(4) . . ?
C43 C44 C45 123.0(5) . . ?
C43 C44 H44 118.5 . . ?
C45 C44 H44 118.5 . . ?
C46 C45 C44 117.2(5) . . ?
C46 C45 H45 121.4 . . ?
C44 C45 H45 121.4 . . ?
C47 C46 F4 118.9(5) . . ?
C47 C46 C45 123.1(5) . . ?
F4 C46 C45 118.0(6) . . ?
C46 C47 C48 118.3(5) . . ?
C46 C47 H47 120.9 . . ?
C48 C47 H47 120.9 . . ?
C47 C48 C43 122.6(5) . . ?
C47 C48 H48 118.7 . . ?
C43 C48 H48 118.7 . . ?
N3 C49 C50 122.5(5) . . ?
N3 C49 H49 118.8 . . ?
C50 C49 H49 118.8 . . ?
C49 C50 C51 118.6(5) . . ?
C49 C50 H50 120.7 . . ?
C51 C50 H50 120.7 . . ?
C50 C51 C52 119.2(5) . . ?
C50 C51 H51 120.4 . . ?
C52 C51 H51 120.4 . . ?
C51 C52 C53 120.4(5) . . ?
C51 C52 H52 119.8 . . ?
C53 C52 H52 119.8 . . ?
N3 C53 C52 119.2(5) . . ?
N3 C53 C54 115.3(5) . . ?
C52 C53 C54 125.4(5) . . ?
C55 C54 C59 120.0(5) . . ?
C55 C54 C53 122.7(5) . . ?
C59 C54 C53 117.2(5) . . ?
C56 C55 C54 120.2(5) . . ?
C56 C55 H55 119.9 . . ?
C54 C55 H55 119.9 . . ?
C57 C56 C55 121.3(5) . . ?
C57 C56 H56 119.4 . . ?
C55 C56 H56 119.4 . . ?
C56 C57 C58 117.7(5) . . ?
C56 C57 C60 120.4(5) . . ?
C58 C57 C60 121.8(5) . . ?
C59 C58 C57 122.8(5) . . ?
C59 C58 H58 118.6 . . ?
C57 C58 H58 118.6 . . ?
C58 C59 C54 117.9(5) . . ?
C58 C59 Au3 128.6(4) . . ?
C54 C59 Au3 113.0(4) . . ?
C57 C60 H60A 109.5 . . ?
C57 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C57 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C66 C61 C62 118.6(5) . . ?
C66 C61 Au3 119.7(4) . . ?
C62 C61 Au3 121.7(4) . . ?
C63 C62 C61 120.6(6) . . ?
C63 C62 H62 119.7 . . ?
C61 C62 H62 119.7 . . ?
C64 C63 C62 119.3(6) . . ?
C64 C63 H63 120.4 . . ?
C62 C63 H63 120.4 . . ?
F5 C64 C63 119.8(6) . . ?
F5 C64 C65 118.2(6) . . ?
C63 C64 C65 122.0(5) . . ?
C64 C65 C66 118.4(6) . . ?
C64 C65 H65 120.8 . . ?
C66 C65 H65 120.8 . . ?
C61 C66 C65 121.1(6) . . ?
C61 C66 H66 119.4 . . ?
C65 C66 H66 119.4 . . ?
C72 C67 C68 117.2(5) . . ?
C72 C67 Au3 120.2(4) . . ?
C68 C67 Au3 122.4(4) . . ?
C69 C68 C67 121.7(5) . . ?
C69 C68 H68 119.1 . . ?
C67 C68 H68 119.1 . . ?
C70 C69 C68 118.9(5) . . ?
C70 C69 H69 120.5 . . ?
C68 C69 H69 120.5 . . ?
F6 C70 C69 119.1(5) . . ?
F6 C70 C71 118.7(5) . . ?
C69 C70 C71 122.2(5) . . ?
C70 C71 C72 118.0(5) . . ?
C70 C71 H71 121.0 . . ?
C72 C71 H71 121.0 . . ?
C67 C72 C71 121.8(5) . . ?
C67 C72 H72 119.1 . . ?
C71 C72 H72 119.1 . . ?
N4 C73 C74 122.1(6) . . ?
N4 C73 H73 118.9 . . ?
C74 C73 H73 118.9 . . ?
C75 C74 C73 118.0(6) . . ?
C75 C74 H74 121.0 . . ?
C73 C74 H74 121.0 . . ?
C76 C75 C74 119.2(6) . . ?
C76 C75 H75 120.4 . . ?
C74 C75 H75 120.4 . . ?
C75 C76 C77 121.4(6) . . ?
C75 C76 H76 119.3 . . ?
C77 C76 H76 119.3 . . ?
N4 C77 C76 118.5(5) . . ?
N4 C77 C78 115.2(5) . . ?
C76 C77 C78 126.3(5) . . ?
C79 C78 C83 119.7(6) . . ?
C79 C78 C77 123.0(6) . . ?
C83 C78 C77 117.4(5) . . ?
C80 C79 C78 120.6(6) . . ?
C80 C79 H79 119.7 . . ?
C78 C79 H79 119.7 . . ?
C79 C80 C81 121.2(6) . . ?
C79 C80 H80 119.4 . . ?
C81 C80 H80 119.4 . . ?
C80 C81 C82 117.9(6) . . ?
C80 C81 C84 120.5(6) . . ?
C82 C81 C84 121.7(7) . . ?
C81 C82 C83 122.0(6) . . ?
C81 C82 H82 119.0 . . ?
C83 C82 H82 119.0 . . ?
C82 C83 C78 118.6(5) . . ?
C82 C83 Au4 128.3(5) . . ?
C78 C83 Au4 112.9(4) . . ?
C81 C84 H84A 109.5 . . ?
C81 C84 H84B 109.5 . . ?
H84A C84 H84B 109.5 . . ?
C81 C84 H84C 109.5 . . ?
H84A C84 H84C 109.5 . . ?
H84B C84 H84C 109.5 . . ?
C90 C85 C86 118.5(5) . . ?
C90 C85 Au4 119.7(4) . . ?
C86 C85 Au4 121.8(4) . . ?
C87 C86 C85 120.8(5) . . ?
C87 C86 H86 119.6 . . ?
C85 C86 H86 119.6 . . ?
C88 C87 C86 119.1(6) . . ?
C88 C87 H87 120.4 . . ?
C86 C87 H87 120.4 . . ?
C87 C88 F7 119.7(6) . . ?
C87 C88 C89 122.1(6) . . ?
F7 C88 C89 118.3(6) . . ?
C88 C89 C90 118.7(6) . . ?
C88 C89 H89 120.7 . . ?
C90 C89 H89 120.7 . . ?
C89 C90 C85 120.8(5) . . ?
C89 C90 H90 119.6 . . ?
C85 C90 H90 119.6 . . ?
C92 C91 C96 117.6(5) . . ?
C92 C91 Au4 121.7(4) . . ?
C96 C91 Au4 120.6(4) . . ?
C93 C92 C91 121.7(5) . . ?
C93 C92 H92 119.1 . . ?
C91 C92 H92 119.1 . . ?
C94 C93 C92 118.4(5) . . ?
C94 C93 H93 120.8 . . ?
C92 C93 H93 120.8 . . ?
F8 C94 C95 118.4(5) . . ?
F8 C94 C93 119.2(5) . . ?
C95 C94 C93 122.4(5) . . ?
C94 C95 C96 118.5(5) . . ?
C94 C95 H95 120.7 . . ?
C96 C95 H95 120.7 . . ?
C95 C96 C91 121.3(5) . . ?
C95 C96 H96 119.4 . . ?
C91 C96 H96 119.4 . . ?
C1 N1 C5 120.8(5) . . ?
C1 N1 Au1 125.6(4) . . ?
C5 N1 Au1 113.6(4) . . ?
C25 N2 C29 120.3(5) . . ?
C25 N2 Au2 125.6(4) . . ?
C29 N2 Au2 114.1(3) . . ?
C49 N3 C53 120.0(5) . . ?
C49 N3 Au3 125.5(4) . . ?
C53 N3 Au3 114.1(4) . . ?
C73 N4 C77 120.7(5) . . ?
C73 N4 Au4 125.0(4) . . ?
C77 N4 Au4 114.2(4) . . ?
C13 Au1 C11 94.4(2) . . ?
C13 Au1 C19 89.4(2) . . ?
C11 Au1 C19 176.1(2) . . ?
C13 Au1 N1 174.7(2) . . ?
C11 Au1 N1 80.6(2) . . ?
C19 Au1 N1 95.59(19) . . ?
C37 Au2 C35 94.1(2) . . ?
C37 Au2 C43 88.6(2) . . ?
C35 Au2 C43 176.7(2) . . ?
C37 Au2 N2 174.15(19) . . ?
C35 Au2 N2 80.28(19) . . ?
C43 Au2 N2 96.95(18) . . ?
C61 Au3 C67 87.4(2) . . ?
C61 Au3 C59 97.4(2) . . ?
C67 Au3 C59 173.4(2) . . ?
C61 Au3 N3 177.3(2) . . ?
C67 Au3 N3 94.85(19) . . ?
C59 Au3 N3 80.2(2) . . ?
C85 Au4 C83 95.5(2) . . ?
C85 Au4 C91 87.6(2) . . ?
C83 Au4 C91 176.5(2) . . ?
C85 Au4 N4 175.20(19) . . ?
C83 Au4 N4 79.9(2) . . ?
C91 Au4 N4 96.97(19) . . ?

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
N1 C1 C2 C3 -0.3(8) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C2 C3 C4 C5 -0.9(8) . . . . ?
C3 C4 C5 N1 1.0(8) . . . . ?
C3 C4 C5 C6 -180.0(5) . . . . ?
N1 C5 C6 C7 -177.7(5) . . . . ?
C4 C5 C6 C7 3.2(8) . . . . ?
N1 C5 C6 C11 1.8(7) . . . . ?
C4 C5 C6 C11 -177.3(5) . . . . ?
C11 C6 C7 C8 1.0(8) . . . . ?
C5 C6 C7 C8 -179.5(5) . . . . ?
C6 C7 C8 C9 0.4(8) . . . . ?
C7 C8 C9 C10 -1.6(8) . . . . ?
C7 C8 C9 C12 178.5(5) . . . . ?
C8 C9 C10 C11 1.5(8) . . . . ?
C12 C9 C10 C11 -178.6(5) . . . . ?
C9 C10 C11 C6 -0.2(8) . . . . ?
C9 C10 C11 Au1 -178.9(4) . . . . ?
C7 C6 C11 C10 -1.0(7) . . . . ?
C5 C6 C11 C10 179.4(5) . . . . ?
C7 C6 C11 Au1 177.8(4) . . . . ?
C5 C6 C11 Au1 -1.7(6) . . . . ?
C18 C13 C14 C15 2.0(8) . . . . ?
Au1 C13 C14 C15 -177.3(4) . . . . ?
C13 C14 C15 C16 -0.7(9) . . . . ?
C14 C15 C16 F1 -179.0(5) . . . . ?
C14 C15 C16 C17 -1.0(10) . . . . ?
C15 C16 C17 C18 1.3(10) . . . . ?
F1 C16 C17 C18 179.3(6) . . . . ?
C16 C17 C18 C13 0.1(9) . . . . ?
C14 C13 C18 C17 -1.7(8) . . . . ?
Au1 C13 C18 C17 177.6(5) . . . . ?
C24 C19 C20 C21 -2.0(8) . . . . ?
Au1 C19 C20 C21 175.0(4) . . . . ?
C19 C20 C21 C22 1.0(8) . . . . ?
C20 C21 C22 C23 -0.1(8) . . . . ?
C20 C21 C22 F2 -178.7(5) . . . . ?
F2 C22 C23 C24 178.9(5) . . . . ?
C21 C22 C23 C24 0.3(8) . . . . ?
C22 C23 C24 C19 -1.5(8) . . . . ?
C20 C19 C24 C23 2.3(8) . . . . ?
Au1 C19 C24 C23 -174.9(4) . . . . ?
N2 C25 C26 C27 -0.4(8) . . . . ?
C25 C26 C27 C28 -0.8(9) . . . . ?
C26 C27 C28 C29 1.3(9) . . . . ?
C27 C28 C29 N2 -0.5(8) . . . . ?
C27 C28 C29 C30 178.7(5) . . . . ?
N2 C29 C30 C31 -179.2(5) . . . . ?
C28 C29 C30 C31 1.6(8) . . . . ?
N2 C29 C30 C35 1.6(7) . . . . ?
C28 C29 C30 C35 -177.7(5) . . . . ?
C35 C30 C31 C32 0.5(8) . . . . ?
C29 C30 C31 C32 -178.7(5) . . . . ?
C30 C31 C32 C33 0.3(8) . . . . ?
C31 C32 C33 C34 -1.2(8) . . . . ?
C31 C32 C33 C36 177.2(5) . . . . ?
C32 C33 C34 C35 1.4(8) . . . . ?
C36 C33 C34 C35 -177.1(5) . . . . ?
C33 C34 C35 C30 -0.6(8) . . . . ?
C33 C34 C35 Au2 -179.7(4) . . . . ?
C31 C30 C35 C34 -0.3(7) . . . . ?
C29 C30 C35 C34 178.9(4) . . . . ?
C31 C30 C35 Au2 178.9(4) . . . . ?
C29 C30 C35 Au2 -1.8(6) . . . . ?
C42 C37 C38 C39 0.5(8) . . . . ?
Au2 C37 C38 C39 -177.5(4) . . . . ?
C37 C38 C39 C40 -0.5(8) . . . . ?
C38 C39 C40 C41 -0.1(9) . . . . ?
C38 C39 C40 F3 -179.1(5) . . . . ?
C39 C40 C41 C42 0.5(9) . . . . ?
F3 C40 C41 C42 179.6(5) . . . . ?
C38 C37 C42 C41 0.0(8) . . . . ?
Au2 C37 C42 C41 178.0(4) . . . . ?
C40 C41 C42 C37 -0.5(8) . . . . ?
C48 C43 C44 C45 0.3(8) . . . . ?
Au2 C43 C44 C45 -179.0(4) . . . . ?
C43 C44 C45 C46 0.7(8) . . . . ?
C44 C45 C46 C47 -1.3(9) . . . . ?
C44 C45 C46 F4 179.6(5) . . . . ?
F4 C46 C47 C48 179.9(5) . . . . ?
C45 C46 C47 C48 0.8(9) . . . . ?
C46 C47 C48 C43 0.4(8) . . . . ?
C44 C43 C48 C47 -0.9(8) . . . . ?
Au2 C43 C48 C47 178.5(4) . . . . ?
N3 C49 C50 C51 0.8(9) . . . . ?
C49 C50 C51 C52 -2.7(8) . . . . ?
C50 C51 C52 C53 2.8(8) . . . . ?
C51 C52 C53 N3 -0.8(8) . . . . ?
C51 C52 C53 C54 175.2(5) . . . . ?
N3 C53 C54 C55 177.9(5) . . . . ?
C52 C53 C54 C55 1.8(8) . . . . ?
N3 C53 C54 C59 1.3(7) . . . . ?
C52 C53 C54 C59 -174.9(5) . . . . ?
C59 C54 C55 C56 1.7(8) . . . . ?
C53 C54 C55 C56 -174.8(5) . . . . ?
C54 C55 C56 C57 -0.4(8) . . . . ?
C55 C56 C57 C58 -0.8(8) . . . . ?
C55 C56 C57 C60 178.9(5) . . . . ?
C56 C57 C58 C59 0.8(8) . . . . ?
C60 C57 C58 C59 -179.0(6) . . . . ?
C57 C58 C59 C54 0.5(8) . . . . ?
C57 C58 C59 Au3 171.9(4) . . . . ?
C55 C54 C59 C58 -1.8(8) . . . . ?
C53 C54 C59 C58 175.0(5) . . . . ?
C55 C54 C59 Au3 -174.4(4) . . . . ?
C53 C54 C59 Au3 2.3(6) . . . . ?
C66 C61 C62 C63 1.4(9) . . . . ?
Au3 C61 C62 C63 -179.2(4) . . . . ?
C61 C62 C63 C64 -1.2(9) . . . . ?
C62 C63 C64 F5 -178.9(6) . . . . ?
C62 C63 C64 C65 -0.2(10) . . . . ?
F5 C64 C65 C66 -179.8(6) . . . . ?
C63 C64 C65 C66 1.5(10) . . . . ?
C62 C61 C66 C65 -0.1(9) . . . . ?
Au3 C61 C66 C65 -179.5(5) . . . . ?
C64 C65 C66 C61 -1.3(9) . . . . ?
C72 C67 C68 C69 -3.7(8) . . . . ?
Au3 C67 C68 C69 170.6(4) . . . . ?
C67 C68 C69 C70 0.7(9) . . . . ?
C68 C69 C70 F6 -177.9(5) . . . . ?
C68 C69 C70 C71 2.3(9) . . . . ?
F6 C70 C71 C72 178.1(5) . . . . ?
C69 C70 C71 C72 -2.2(9) . . . . ?
C68 C67 C72 C71 3.8(8) . . . . ?
Au3 C67 C72 C71 -170.6(4) . . . . ?
C70 C71 C72 C67 -1.0(9) . . . . ?
N4 C73 C74 C75 0.0(9) . . . . ?
C73 C74 C75 C76 -0.5(9) . . . . ?
C74 C75 C76 C77 0.4(9) . . . . ?
C75 C76 C77 N4 0.1(8) . . . . ?
C75 C76 C77 C78 -179.2(5) . . . . ?
N4 C77 C78 C79 177.7(5) . . . . ?
C76 C77 C78 C79 -3.1(9) . . . . ?
N4 C77 C78 C83 -1.7(7) . . . . ?
C76 C77 C78 C83 177.5(5) . . . . ?
C83 C78 C79 C80 -1.8(9) . . . . ?
C77 C78 C79 C80 178.9(5) . . . . ?
C78 C79 C80 C81 1.7(9) . . . . ?
C79 C80 C81 C82 -1.0(9) . . . . ?
C79 C80 C81 C84 179.7(6) . . . . ?
C80 C81 C82 C83 0.4(8) . . . . ?
C84 C81 C82 C83 179.7(5) . . . . ?
C81 C82 C83 C78 -0.5(8) . . . . ?
C81 C82 C83 Au4 173.2(4) . . . . ?
C79 C78 C83 C82 1.1(8) . . . . ?
C77 C78 C83 C82 -179.5(5) . . . . ?
C79 C78 C83 Au4 -173.4(4) . . . . ?
C77 C78 C83 Au4 6.0(6) . . . . ?
C90 C85 C86 C87 1.3(8) . . . . ?
Au4 C85 C86 C87 -176.5(4) . . . . ?
C85 C86 C87 C88 -1.0(9) . . . . ?
C86 C87 C88 F7 -179.9(5) . . . . ?
C86 C87 C88 C89 0.0(9) . . . . ?
C87 C88 C89 C90 0.5(9) . . . . ?
F7 C88 C89 C90 -179.5(5) . . . . ?
C88 C89 C90 C85 -0.1(9) . . . . ?
C86 C85 C90 C89 -0.8(8) . . . . ?
Au4 C85 C90 C89 177.0(4) . . . . ?
C96 C91 C92 C93 0.2(8) . . . . ?
Au4 C91 C92 C93 -177.1(4) . . . . ?
C91 C92 C93 C94 0.5(8) . . . . ?
C92 C93 C94 F8 178.4(5) . . . . ?
C92 C93 C94 C95 -0.1(8) . . . . ?
F8 C94 C95 C96 -179.6(5) . . . . ?
C93 C94 C95 C96 -1.1(9) . . . . ?
C94 C95 C96 C91 1.8(9) . . . . ?
C92 C91 C96 C95 -1.4(8) . . . . ?
Au4 C91 C96 C95 175.9(4) . . . . ?
C2 C1 N1 C5 0.5(8) . . . . ?
C2 C1 N1 Au1 -178.4(4) . . . . ?
C4 C5 N1 C1 -0.8(7) . . . . ?
C6 C5 N1 C1 -179.9(5) . . . . ?
C4 C5 N1 Au1 178.2(4) . . . . ?
C6 C5 N1 Au1 -0.9(5) . . . . ?
C26 C25 N2 C29 1.1(8) . . . . ?
C26 C25 N2 Au2 -178.2(4) . . . . ?
C28 C29 N2 C25 -0.7(7) . . . . ?
C30 C29 N2 C25 180.0(4) . . . . ?
C28 C29 N2 Au2 178.8(4) . . . . ?
C30 C29 N2 Au2 -0.6(5) . . . . ?
C50 C49 N3 C53 1.2(8) . . . . ?
C50 C49 N3 Au3 -171.4(4) . . . . ?
C52 C53 N3 C49 -1.2(8) . . . . ?
C54 C53 N3 C49 -177.6(5) . . . . ?
C52 C53 N3 Au3 172.3(4) . . . . ?
C54 C53 N3 Au3 -4.1(6) . . . . ?
C74 C73 N4 C77 0.4(8) . . . . ?
C74 C73 N4 Au4 -177.1(4) . . . . ?
C76 C77 N4 C73 -0.5(8) . . . . ?
C78 C77 N4 C73 178.8(5) . . . . ?
C76 C77 N4 Au4 177.3(4) . . . . ?
C78 C77 N4 Au4 -3.4(6) . . . . ?

_refine_diff_density_max         5.082
_refine_diff_density_min         -1.545
_refine_diff_density_rms         0.157

_shelxl_version_number           2012-9

_database_code_depnum_ccdc_archive 'CCDC 1009035'
#######################################################################
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#                                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
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_Quest14mz082_0m_twin

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 Au F6 N, C H2 Cl2'
_chemical_formula_sum            'C27 H20 Au Cl2 F6 N'
_chemical_formula_weight         740.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.3340(11)
_cell_length_b                   11.4331(13)
_cell_length_c                   12.8416(17)
_cell_angle_alpha                73.407(4)
_cell_angle_beta                 81.938(4)
_cell_angle_gamma                73.869(3)
_cell_volume                     1258.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.2750
_cell_measurement_theta_max      30.6050

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.118
_shelx_estimated_absorpt_T_min   0.360
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3664
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Apex2 v2014.1-1 (Bruker, 2014)'

_exptl_special_details           
;
The crystal under investigation was found to be non-merohedrally 
twinned. The orientation matrices for the two components were 
identified using the program Cell_Now, with the two components 
being related by a 180 degree rotation around the real  
a-axis. The two components were initially integrated using Saint 
giving the following twin matrix: 

     0.99994  0.01611 -0.03295
     0.69290 -0.98912 -0.02860
     0.32732  0.02563 -1.01045

Integration proofed problematic due to excessive multiple overlap 
of reflections, resulting in large numbers of rejected reflections. 
Attempts were made to adjust integration parameters to avoid excessive 
rejections (through adjustements to integration queue size, blending of 
profiles, integration box slicing and twin overlap parameters), which 
led to less but still substantial numbers of rejected reflections. 
With no complete dataset obtainable through simultaneous integration 
of both twin domains, the data were instead handled as if not twinned, 
with only the major domain integrated, and converted into an hklf 5 
type format hkl file after integration using the "Make HKLF5 File" 
routine as implemented in WinGX. The twin law matrix was used as 
obtained from SAINT, see above. The Overlap R1 and R2 values used 
were 0.32, i.e. reflections with a discriminator function less or 
equal to overlap radius of 0.32 were counted overlapped, all others 
as single. The discriminator fucntion used was the "delta function 
on index non-integrality". No reflections were omitted. 

The structure was solved using direct methods with the hklf 4 type 
file and was refined using the hklf 5 type file, resulting in a BASF 
value of 0.199(4).

A refinement using the incomplete data obtained through SAINT and 
TWINABS gave similar refinement statistics, but with higher overall 
R values (around 8-9% for R1) and with less well defined ADPs (two 
atoms NPD or close to NPD).

No Rint value is obtainable for the hklf 5 type file using the WinGX 
routine. The value from TWINABS is given instead, which is for all 
reflections available and is based on agreement between observed 
single and composite intensities and those calculated from refined 
unique intensities and twin fractions (TWINABS (Sheldrick, 2009)).
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20316
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.188
_diffrn_reflns_theta_max         31.004
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             20316
_reflns_number_gt                18797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'Apex2 v2014.1-1 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev645 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+38.3672P] 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         20316
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.1752
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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_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 0.7624(13) 0.2556(10) 0.7325(10) 0.031(2) Uani 1 1 d . . . . .
H1 H 0.7837 0.2127 0.6766 0.037 Uiso 1 1 calc R U . . .
C2 C 0.7561(13) 0.1876(10) 0.8394(10) 0.031(2) Uani 1 1 d . . . . .
H2 H 0.7743 0.0984 0.8570 0.037 Uiso 1 1 calc R U . . .
C3 C 0.7224(16) 0.2506(12) 0.9234(12) 0.042(3) Uani 1 1 d . . . . .
H3 H 0.7171 0.2048 0.9977 0.051 Uiso 1 1 calc R U . . .
C4 C 0.6975(15) 0.3805(12) 0.8948(10) 0.037(3) Uani 1 1 d . . . . .
H4 H 0.6727 0.4258 0.9491 0.045 Uiso 1 1 calc R U . . .
C5 C 0.7093(12) 0.4446(10) 0.7838(8) 0.025(2) Uani 1 1 d . . . . .
C6 C 0.6837(12) 0.5838(9) 0.7434(9) 0.025(2) Uani 1 1 d . . . . .
C7 C 0.6523(14) 0.6644(10) 0.8125(10) 0.031(2) Uani 1 1 d . . . . .
H7 H 0.6437 0.6306 0.8891 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6337(15) 0.7924(11) 0.7698(11) 0.038(3) Uani 1 1 d . . . . .
H8 H 0.6119 0.8461 0.8174 0.046 Uiso 1 1 calc R U . . .
C9 C 0.6463(12) 0.8433(10) 0.6588(9) 0.026(2) Uani 1 1 d . . . . .
C10 C 0.6779(11) 0.7634(10) 0.5899(9) 0.026(2) Uani 1 1 d . . . . .
H10 H 0.6856 0.7990 0.5135 0.031 Uiso 1 1 calc R U . . .
C11 C 0.6988(11) 0.6321(9) 0.6292(9) 0.0217(19) Uani 1 1 d . . . . .
C12 C 0.6230(14) 0.9849(10) 0.6130(10) 0.034(2) Uani 1 1 d . . . . .
H12A H 0.6584 1.0032 0.5359 0.050 Uiso 1 1 calc R U . . .
H12B H 0.6791 1.0163 0.6534 0.050 Uiso 1 1 calc R U . . .
H12C H 0.5163 1.0263 0.6200 0.050 Uiso 1 1 calc R U . . .
C13 C 0.7868(11) 0.3569(8) 0.4635(8) 0.0190(18) Uani 1 1 d . . . . .
C14 C 0.9245(12) 0.2670(10) 0.4671(10) 0.028(2) Uani 1 1 d . . . . .
H14 H 1.0004 0.2717 0.5068 0.034 Uiso 1 1 calc R U . . .
C15 C 0.9539(13) 0.1713(10) 0.4147(10) 0.029(2) Uani 1 1 d . . . . .
H15 H 1.0484 0.1119 0.4181 0.035 Uiso 1 1 calc R U . . .
C16 C 0.8431(12) 0.1638(10) 0.3574(9) 0.026(2) Uani 1 1 d . . . . .
C17 C 0.7052(12) 0.2493(9) 0.3533(9) 0.025(2) Uani 1 1 d . . . . .
H17 H 0.6299 0.2442 0.3132 0.030 Uiso 1 1 calc R U . . .
C18 C 0.6769(11) 0.3439(10) 0.4088(9) 0.024(2) Uani 1 1 d . . . . .
H18 H 0.5803 0.3999 0.4088 0.029 Uiso 1 1 calc R U . . .
C19 C 0.8707(14) 0.0605(11) 0.3003(11) 0.035(3) Uani 1 1 d . . . . .
C20 C 0.7474(10) 0.6159(9) 0.3981(8) 0.0170(17) Uani 1 1 d . . . . .
C21 C 0.6110(11) 0.6983(10) 0.3538(10) 0.029(2) Uani 1 1 d . . . . .
H21 H 0.5184 0.6948 0.3945 0.034 Uiso 1 1 calc R U . . .
C22 C 0.6131(13) 0.7819(10) 0.2530(10) 0.030(2) Uani 1 1 d . . . . .
H22 H 0.5216 0.8347 0.2246 0.036 Uiso 1 1 calc R U . . .
C23 C 0.7468(13) 0.7908(10) 0.1919(10) 0.030(2) Uani 1 1 d . . . . .
C24 C 0.8794(13) 0.7136(11) 0.2321(10) 0.031(2) Uani 1 1 d . . . . .
H24 H 0.9712 0.7212 0.1916 0.038 Uiso 1 1 calc R U . . .
C25 C 0.8799(12) 0.6256(11) 0.3310(8) 0.025(2) Uani 1 1 d . . . . .
H25 H 0.9721 0.5694 0.3550 0.030 Uiso 1 1 calc R U . . .
C26 C 0.7416(15) 0.8835(12) 0.0820(11) 0.038(3) Uani 1 1 d . . . . .
C27 C 0.8913(19) 0.4469(15) 0.1556(13) 0.052(4) Uani 1 1 d . . . . .
H27A H 0.8986 0.4081 0.2347 0.062 Uiso 1 1 calc R U . . .
H27B H 0.9464 0.5136 0.1347 0.062 Uiso 1 1 calc R U . . .
Au1 Au 0.74345(4) 0.49751(3) 0.54403(3) 0.02096(12) Uani 1 1 d . . . . .
Cl1 Cl 0.9773(5) 0.3306(4) 0.0847(4) 0.0595(10) Uani 1 1 d . . . . .
Cl2 Cl 0.7044(5) 0.5154(4) 0.1294(3) 0.0549(9) Uani 1 1 d . . . . .
F1 F 0.8274(12) -0.0406(7) 0.3618(8) 0.058(2) Uani 1 1 d . . . . .
F2 F 1.0162(10) 0.0171(9) 0.2739(9) 0.060(2) Uani 1 1 d . . . . .
F3 F 0.7993(12) 0.0953(8) 0.2090(7) 0.061(3) Uani 1 1 d . . . . .
F4 F 0.6401(10) 0.9925(7) 0.0783(7) 0.049(2) Uani 1 1 d . . . . .
F5 F 0.8726(9) 0.9122(8) 0.0474(7) 0.054(2) Uani 1 1 d . . . . .
F6 F 0.7073(13) 0.8392(9) 0.0044(7) 0.062(3) Uani 1 1 d . . . . .
N1 N 0.7390(10) 0.3826(8) 0.7051(7) 0.0247(18) 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 N1 1.354(13) . ?
C1 C2 1.374(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.42(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(15) . ?
C4 H4 0.9500 . ?
C5 N1 1.350(14) . ?
C5 C6 1.486(14) . ?
C6 C7 1.402(15) . ?
C6 C11 1.415(14) . ?
C7 C8 1.378(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(15) . ?
C9 C12 1.520(14) . ?
C10 C11 1.406(13) . ?
C10 H10 0.9500 . ?
C11 Au1 2.053(10) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.383(13) . ?
C13 C14 1.403(14) . ?
C13 Au1 2.071(10) . ?
C14 C15 1.388(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(15) . ?
C16 C19 1.507(16) . ?
C17 C18 1.406(15) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 F1 1.331(14) . ?
C19 F3 1.335(15) . ?
C19 F2 1.341(15) . ?
C20 C25 1.416(13) . ?
C20 C21 1.436(13) . ?
C20 Au1 1.976(9) . ?
C21 C22 1.373(16) . ?
C21 H21 0.9500 . ?
C22 C23 1.391(16) . ?
C22 H22 0.9500 . ?
C23 C24 1.375(16) . ?
C23 C26 1.501(16) . ?
C24 C25 1.377(15) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 F4 1.333(15) . ?
C26 F5 1.337(15) . ?
C26 F6 1.348(16) . ?
C27 Cl2 1.739(18) . ?
C27 Cl1 1.770(16) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
Au1 N1 2.112(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 121.4(12) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C1 C2 C3 119.9(11) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 118.4(12) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 119.0(13) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.4(10) . . ?
N1 C5 C6 114.8(9) . . ?
C4 C5 C6 123.7(10) . . ?
C7 C6 C11 120.6(9) . . ?
C7 C6 C5 123.3(10) . . ?
C11 C6 C5 116.0(9) . . ?
C8 C7 C6 120.4(11) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.7(11) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 119.0(10) . . ?
C8 C9 C12 120.1(10) . . ?
C10 C9 C12 120.8(10) . . ?
C9 C10 C11 122.5(10) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C6 116.7(10) . . ?
C10 C11 Au1 129.3(8) . . ?
C6 C11 Au1 114.0(7) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 117.2(9) . . ?
C18 C13 Au1 120.8(8) . . ?
C14 C13 Au1 121.8(7) . . ?
C15 C14 C13 122.3(10) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C16 C15 C14 118.9(10) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C15 120.6(10) . . ?
C17 C16 C19 119.1(10) . . ?
C15 C16 C19 120.3(10) . . ?
C16 C17 C18 119.5(10) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C13 C18 C17 121.4(10) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
F1 C19 F3 105.6(10) . . ?
F1 C19 F2 104.7(11) . . ?
F3 C19 F2 107.1(11) . . ?
F1 C19 C16 112.8(11) . . ?
F3 C19 C16 113.5(10) . . ?
F2 C19 C16 112.4(10) . . ?
C25 C20 C21 116.0(9) . . ?
C25 C20 Au1 123.7(7) . . ?
C21 C20 Au1 120.3(7) . . ?
C22 C21 C20 120.6(10) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 121.2(11) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 119.6(11) . . ?
C24 C23 C26 121.7(11) . . ?
C22 C23 C26 118.7(11) . . ?
C23 C24 C25 120.3(10) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 122.2(10) . . ?
C24 C25 H25 118.9 . . ?
C20 C25 H25 118.9 . . ?
F4 C26 F5 106.4(10) . . ?
F4 C26 F6 105.2(11) . . ?
F5 C26 F6 106.0(12) . . ?
F4 C26 C23 113.8(11) . . ?
F5 C26 C23 112.4(10) . . ?
F6 C26 C23 112.3(10) . . ?
Cl2 C27 Cl1 113.1(9) . . ?
Cl2 C27 H27A 109.0 . . ?
Cl1 C27 H27A 109.0 . . ?
Cl2 C27 H27B 109.0 . . ?
Cl1 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C20 Au1 C11 95.8(4) . . ?
C20 Au1 C13 86.3(4) . . ?
C11 Au1 C13 177.9(4) . . ?
C20 Au1 N1 175.6(3) . . ?
C11 Au1 N1 79.9(4) . . ?
C13 Au1 N1 98.1(3) . . ?
C5 N1 C1 119.9(10) . . ?
C5 N1 Au1 115.3(7) . . ?
C1 N1 Au1 124.9(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.9(18) . . . . ?
C1 C2 C3 C4 -0.4(19) . . . . ?
C2 C3 C4 C5 -1.2(19) . . . . ?
C3 C4 C5 N1 2.4(18) . . . . ?
C3 C4 C5 C6 179.5(11) . . . . ?
N1 C5 C6 C7 -179.6(11) . . . . ?
C4 C5 C6 C7 3.1(18) . . . . ?
N1 C5 C6 C11 -2.1(14) . . . . ?
C4 C5 C6 C11 -179.3(11) . . . . ?
C11 C6 C7 C8 0.8(18) . . . . ?
C5 C6 C7 C8 178.2(11) . . . . ?
C6 C7 C8 C9 -0.3(19) . . . . ?
C7 C8 C9 C10 0.2(18) . . . . ?
C7 C8 C9 C12 179.0(11) . . . . ?
C8 C9 C10 C11 -0.6(16) . . . . ?
C12 C9 C10 C11 -179.4(10) . . . . ?
C9 C10 C11 C6 1.1(15) . . . . ?
C9 C10 C11 Au1 179.2(8) . . . . ?
C7 C6 C11 C10 -1.2(15) . . . . ?
C5 C6 C11 C10 -178.8(9) . . . . ?
C7 C6 C11 Au1 -179.6(9) . . . . ?
C5 C6 C11 Au1 2.8(12) . . . . ?
C18 C13 C14 C15 2.7(15) . . . . ?
Au1 C13 C14 C15 179.0(8) . . . . ?
C13 C14 C15 C16 -0.4(17) . . . . ?
C14 C15 C16 C17 -0.7(17) . . . . ?
C14 C15 C16 C19 -179.5(10) . . . . ?
C15 C16 C17 C18 -0.6(16) . . . . ?
C19 C16 C17 C18 178.2(10) . . . . ?
C14 C13 C18 C17 -4.0(14) . . . . ?
Au1 C13 C18 C17 179.6(7) . . . . ?
C16 C17 C18 C13 3.1(15) . . . . ?
C17 C16 C19 F1 -86.3(14) . . . . ?
C15 C16 C19 F1 92.6(13) . . . . ?
C17 C16 C19 F3 33.9(15) . . . . ?
C15 C16 C19 F3 -147.3(11) . . . . ?
C17 C16 C19 F2 155.7(11) . . . . ?
C15 C16 C19 F2 -25.5(16) . . . . ?
C25 C20 C21 C22 -1.2(15) . . . . ?
Au1 C20 C21 C22 179.1(8) . . . . ?
C20 C21 C22 C23 -1.0(18) . . . . ?
C21 C22 C23 C24 0.7(18) . . . . ?
C21 C22 C23 C26 179.6(11) . . . . ?
C22 C23 C24 C25 1.9(18) . . . . ?
C26 C23 C24 C25 -177.0(11) . . . . ?
C23 C24 C25 C20 -4.2(17) . . . . ?
C21 C20 C25 C24 3.8(15) . . . . ?
Au1 C20 C25 C24 -176.5(8) . . . . ?
C24 C23 C26 F4 -142.2(12) . . . . ?
C22 C23 C26 F4 38.8(16) . . . . ?
C24 C23 C26 F5 -21.1(18) . . . . ?
C22 C23 C26 F5 159.9(11) . . . . ?
C24 C23 C26 F6 98.3(15) . . . . ?
C22 C23 C26 F6 -80.6(15) . . . . ?
C4 C5 N1 C1 -1.9(17) . . . . ?
C6 C5 N1 C1 -179.2(10) . . . . ?
C4 C5 N1 Au1 177.7(9) . . . . ?
C6 C5 N1 Au1 0.3(12) . . . . ?
C2 C1 N1 C5 0.2(16) . . . . ?
C2 C1 N1 Au1 -179.3(8) . . . . ?

_refine_diff_density_max         9.457
_refine_diff_density_min         -4.269
_refine_diff_density_rms         0.401

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 1009036'
#######################################################################
#
#                 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_Quest14mz097_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Au N3 O4'
_chemical_formula_weight         609.38

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.1263(3)
_cell_length_b                   14.1527(4)
_cell_length_c                   26.2319(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4130.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9856
_cell_measurement_theta_min      2.3284
_cell_measurement_theta_max      30.5163

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_F_000             2352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    7.161
_shelx_estimated_absorpt_T_min   0.394
_shelx_estimated_absorpt_T_max   0.480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5873
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Apex2 v2014.1-1 (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23940
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.328
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5103
_reflns_number_gt                4447
_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       'Apex2 v2014.1-1 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev645 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0059P)²+28.2499P] 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         5103
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0573
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
C1 C 0.2712(4) 0.3646(3) 0.49897(16) 0.0205(9) Uani 1 1 d . . . . .
H1 H 0.3266 0.3703 0.4716 0.025 Uiso 1 1 calc R U . . .
C2 C 0.3159(4) 0.3520(3) 0.54771(16) 0.0218(9) Uani 1 1 d . . . . .
H2 H 0.4000 0.3501 0.5539 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2351(4) 0.3421(3) 0.58702(17) 0.0244(9) Uani 1 1 d . . . . .
H3 H 0.2629 0.3326 0.6209 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1140(4) 0.3460(3) 0.57704(16) 0.0214(9) Uani 1 1 d . . . . .
H4 H 0.0581 0.3381 0.6041 0.026 Uiso 1 1 calc R U . . .
C5 C 0.0724(4) 0.3616(3) 0.52739(15) 0.0168(8) Uani 1 1 d . . . . .
C6 C -0.0531(4) 0.3697(3) 0.51171(15) 0.0168(8) Uani 1 1 d . . . . .
C7 C -0.1487(4) 0.3641(3) 0.54645(16) 0.0215(9) Uani 1 1 d . . . . .
H7 H -0.1331 0.3551 0.5817 0.026 Uiso 1 1 calc R U . . .
C8 C -0.2655(4) 0.3717(3) 0.52915(16) 0.0214(9) Uani 1 1 d . . . . .
H8 H -0.3299 0.3656 0.5527 0.026 Uiso 1 1 calc R U . . .
C9 C -0.2910(4) 0.3881(3) 0.47800(16) 0.0201(8) Uani 1 1 d . . . . .
C10 C -0.1953(4) 0.3940(3) 0.44374(17) 0.0202(9) Uani 1 1 d . . . . .
H10 H -0.2116 0.4051 0.4087 0.024 Uiso 1 1 calc R U . . .
C11 C -0.0769(4) 0.3842(3) 0.45948(14) 0.0164(8) Uani 1 1 d . . . . .
C12 C -0.4177(4) 0.3967(3) 0.45910(18) 0.0270(10) Uani 1 1 d . . . . .
H12A H -0.4693 0.3528 0.4779 0.041 Uiso 1 1 calc R U . . .
H12B H -0.4204 0.3816 0.4227 0.041 Uiso 1 1 calc R U . . .
H12C H -0.4461 0.4615 0.4644 0.041 Uiso 1 1 calc R U . . .
C13 C -0.0177(3) 0.3895(3) 0.34966(14) 0.0139(7) Uani 1 1 d . . . . .
C14 C -0.0629(4) 0.3093(3) 0.32639(16) 0.0232(9) Uani 1 1 d . . . . .
H14 H -0.0418 0.2488 0.3393 0.028 Uiso 1 1 calc R U . . .
C15 C -0.1393(5) 0.3159(3) 0.28411(18) 0.0273(10) Uani 1 1 d . . . . .
H15 H -0.1692 0.2601 0.2685 0.033 Uiso 1 1 calc R U . . .
C16 C -0.1711(4) 0.4036(3) 0.26512(16) 0.0231(9) Uani 1 1 d . . . . .
H16 H -0.2238 0.4093 0.2368 0.028 Uiso 1 1 calc R U . . .
C17 C -0.1239(4) 0.4826(3) 0.28857(16) 0.0207(9) Uani 1 1 d . . . . .
C18 C -0.0473(4) 0.4773(3) 0.33031(16) 0.0211(9) Uani 1 1 d . . . . .
H18 H -0.0157 0.5331 0.3453 0.025 Uiso 1 1 calc R U . . .
C19 C 0.2342(4) 0.3721(3) 0.37377(13) 0.0161(8) Uani 1 1 d . . . . .
C20 C 0.2700(4) 0.2887(3) 0.34891(15) 0.0209(9) Uani 1 1 d . . . . .
H20 H 0.2186 0.2351 0.3500 0.025 Uiso 1 1 calc R U . . .
C21 C 0.3786(4) 0.2825(3) 0.32281(16) 0.0232(9) Uani 1 1 d . . . . .
H21 H 0.4006 0.2249 0.3067 0.028 Uiso 1 1 calc R U . . .
C22 C 0.4547(4) 0.3596(3) 0.32008(17) 0.0258(10) Uani 1 1 d . . . . .
H22 H 0.5294 0.3561 0.3026 0.031 Uiso 1 1 calc R U . . .
C23 C 0.4180(4) 0.4422(3) 0.34373(16) 0.0220(9) Uani 1 1 d . . . . .
C24 C 0.3102(4) 0.4494(3) 0.37007(15) 0.0196(9) Uani 1 1 d . . . . .
H24 H 0.2884 0.5075 0.3856 0.024 Uiso 1 1 calc R U . . .
N1 N 0.1541(3) 0.3692(2) 0.48872(12) 0.0167(7) Uani 1 1 d . . . . .
N2 N -0.1569(4) 0.5766(3) 0.26884(14) 0.0258(9) Uani 1 1 d . . . . .
N3 N 0.4970(4) 0.5257(3) 0.34233(17) 0.0343(10) Uani 1 1 d . . . . .
O1 O -0.2209(4) 0.5807(3) 0.23034(13) 0.0398(9) Uani 1 1 d . . . . .
O2 O -0.1198(4) 0.6467(2) 0.29135(13) 0.0356(9) Uani 1 1 d . . . . .
O3 O 0.4678(4) 0.5959(3) 0.36700(15) 0.0381(9) Uani 1 1 d . . . . .
O4 O 0.5890(4) 0.5218(3) 0.3171(2) 0.0677(16) Uani 1 1 d . . . . .
Au1 Au 0.07609(2) 0.38044(2) 0.41557(2) 0.01451(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
C1 N1 1.332(6) . ?
C1 C2 1.384(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(6) . ?
C4 H4 0.9500 . ?
C5 N1 1.366(5) . ?
C5 C6 1.460(6) . ?
C6 C7 1.403(6) . ?
C6 C11 1.411(5) . ?
C7 C8 1.381(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(6) . ?
C9 C12 1.499(6) . ?
C10 C11 1.387(6) . ?
C10 H10 0.9500 . ?
C11 Au1 2.056(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.381(6) . ?
C13 C14 1.384(6) . ?
C13 Au1 2.024(4) . ?
C14 C15 1.400(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(6) . ?
C17 N2 1.475(6) . ?
C18 H18 0.9500 . ?
C19 C24 1.386(6) . ?
C19 C20 1.406(6) . ?
C19 Au1 2.076(4) . ?
C20 C21 1.391(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(6) . ?
C23 N3 1.474(6) . ?
C24 H24 0.9500 . ?
N1 Au1 2.112(3) . ?
N2 O2 1.226(5) . ?
N2 O1 1.237(5) . ?
N3 O4 1.221(6) . ?
N3 O3 1.228(5) . ?

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 123.0(4) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.2(4) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 118.9(4) . . ?
N1 C5 C6 114.9(3) . . ?
C4 C5 C6 126.2(4) . . ?
C7 C6 C11 119.8(4) . . ?
C7 C6 C5 122.5(4) . . ?
C11 C6 C5 117.7(4) . . ?
C8 C7 C6 119.7(4) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 121.4(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 118.4(4) . . ?
C8 C9 C12 121.6(4) . . ?
C10 C9 C12 120.0(4) . . ?
C11 C10 C9 121.8(4) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C6 118.8(4) . . ?
C10 C11 Au1 128.5(3) . . ?
C6 C11 Au1 112.6(3) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 119.3(4) . . ?
C18 C13 Au1 119.6(3) . . ?
C14 C13 Au1 120.8(3) . . ?
C13 C14 C15 121.0(4) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 118.0(4) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C16 C17 C18 122.7(4) . . ?
C16 C17 N2 118.7(4) . . ?
C18 C17 N2 118.6(4) . . ?
C13 C18 C17 119.0(4) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C24 C19 C20 117.2(4) . . ?
C24 C19 Au1 120.6(3) . . ?
C20 C19 Au1 122.2(3) . . ?
C21 C20 C19 121.8(4) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C22 C21 C20 120.5(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 117.5(4) . . ?
C21 C22 H22 121.2 . . ?
C23 C22 H22 121.2 . . ?
C22 C23 C24 122.7(4) . . ?
C22 C23 N3 119.4(4) . . ?
C24 C23 N3 117.9(4) . . ?
C19 C24 C23 120.3(4) . . ?
C19 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C1 N1 C5 119.8(4) . . ?
C1 N1 Au1 126.1(3) . . ?
C5 N1 Au1 114.0(3) . . ?
O2 N2 O1 123.4(4) . . ?
O2 N2 C17 118.5(4) . . ?
O1 N2 C17 118.1(4) . . ?
O4 N3 O3 122.9(5) . . ?
O4 N3 C23 118.5(4) . . ?
O3 N3 C23 118.6(4) . . ?
C13 Au1 C11 92.87(15) . . ?
C13 Au1 C19 89.38(15) . . ?
C11 Au1 C19 177.22(15) . . ?
C13 Au1 N1 173.22(14) . . ?
C11 Au1 N1 80.41(15) . . ?
C19 Au1 N1 97.32(14) . . ?

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
N1 C1 C2 C3 1.2(7) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C3 C4 C5 N1 2.5(6) . . . . ?
C3 C4 C5 C6 -178.3(4) . . . . ?
N1 C5 C6 C7 -179.7(4) . . . . ?
C4 C5 C6 C7 1.1(7) . . . . ?
N1 C5 C6 C11 0.1(5) . . . . ?
C4 C5 C6 C11 -179.1(4) . . . . ?
C11 C6 C7 C8 0.7(6) . . . . ?
C5 C6 C7 C8 -179.5(4) . . . . ?
C6 C7 C8 C9 -2.2(7) . . . . ?
C7 C8 C9 C10 1.9(6) . . . . ?
C7 C8 C9 C12 -179.8(4) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
C12 C9 C10 C11 -178.5(4) . . . . ?
C9 C10 C11 C6 -1.3(6) . . . . ?
C9 C10 C11 Au1 175.0(3) . . . . ?
C7 C6 C11 C10 1.0(6) . . . . ?
C5 C6 C11 C10 -178.8(4) . . . . ?
C7 C6 C11 Au1 -175.9(3) . . . . ?
C5 C6 C11 Au1 4.4(5) . . . . ?
C18 C13 C14 C15 -0.9(7) . . . . ?
Au1 C13 C14 C15 172.6(4) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
C14 C15 C16 C17 1.0(7) . . . . ?
C15 C16 C17 C18 -0.5(7) . . . . ?
C15 C16 C17 N2 -180.0(4) . . . . ?
C14 C13 C18 C17 1.4(6) . . . . ?
Au1 C13 C18 C17 -172.2(3) . . . . ?
C16 C17 C18 C13 -0.7(7) . . . . ?
N2 C17 C18 C13 178.8(4) . . . . ?
C24 C19 C20 C21 1.8(6) . . . . ?
Au1 C19 C20 C21 -177.2(3) . . . . ?
C19 C20 C21 C22 -0.7(7) . . . . ?
C20 C21 C22 C23 -0.6(7) . . . . ?
C21 C22 C23 C24 0.8(7) . . . . ?
C21 C22 C23 N3 179.3(4) . . . . ?
C20 C19 C24 C23 -1.5(6) . . . . ?
Au1 C19 C24 C23 177.5(3) . . . . ?
C22 C23 C24 C19 0.2(7) . . . . ?
N3 C23 C24 C19 -178.2(4) . . . . ?
C2 C1 N1 C5 0.2(6) . . . . ?
C2 C1 N1 Au1 -176.2(3) . . . . ?
C4 C5 N1 C1 -2.0(6) . . . . ?
C6 C5 N1 C1 178.7(4) . . . . ?
C4 C5 N1 Au1 174.8(3) . . . . ?
C6 C5 N1 Au1 -4.4(4) . . . . ?
C16 C17 N2 O2 176.3(4) . . . . ?
C18 C17 N2 O2 -3.2(6) . . . . ?
C16 C17 N2 O1 -3.6(6) . . . . ?
C18 C17 N2 O1 176.9(4) . . . . ?
C22 C23 N3 O4 5.2(7) . . . . ?
C24 C23 N3 O4 -176.3(5) . . . . ?
C22 C23 N3 O3 -174.1(5) . . . . ?
C24 C23 N3 O3 4.4(7) . . . . ?

_refine_diff_density_max         3.255
_refine_diff_density_min         -1.347
_refine_diff_density_rms         0.132

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1009037'
#######################################################################
#
#                 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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Quest14mz078_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 Au N S2'
_chemical_formula_weight         631.54

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'
S S 0.1246 0.1234 '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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   35.5669(9)
_cell_length_b                   35.5669(9)
_cell_length_c                   7.2973(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9231.1(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.8559
_cell_measurement_theta_max      54.5030

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_F_000             4896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    6.572
_shelx_estimated_absorpt_T_min   0.290
_shelx_estimated_absorpt_T_max   0.401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3979
_exptl_absorpt_correction_T_max  0.7509
_exptl_absorpt_process_details   'Apex2 v2014.1-1 (Bruker, 2014)'

_exptl_special_details           
;
The compound exhibits two different types of disorder. Thiophene rings are 
disordered by 180 degree rotations around the Au-C bond. In addition, whole 
molecule disorder is observed due to 180 rotation of the tpy ligand which, 
due to the steric demand if the methyl group, induces a shift of the whole 
molecule. The disorder of the tpy ligand and of the the two thiophene 
moieties are independent of each other, thus leading to eight different 
combinations of disordered moieties. Due to their low prevalence, the minor 
flip disordered thiophene moieties associated with the minor rotated tpy 
ligand were omitted from the refinement. 

All chemically equivalent disordered organic moieties were restrained to 
have similar geometries (SAME restraint of Shelxl). The gold bonded carbon 
atoms of equivalent flip disordered thiophene units were constrained to have 
identical positions and ADPs. The Au-C and Au-N distances of the flip 
disordered tpy ligand were restrained to be similar to that of the major 
moiety complex. All disordered atoms were subjected to a rigid bond restraint 
(RIGU in Shelxl). Overlapping atoms C22B and S2 were restrained to have similar 
ADPs (SIMU in Shelxl). Overlapping atoms C15 and C15C, C16 and C16C, C5 and C6C, 
and C4 and C7C were constrained to have identical ADPs. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            83233
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7052
_reflns_number_gt                6761
_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       'Apex2 v2014.1-1 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev645 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+59.5458P] 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         7052
_refine_ls_number_parameters     699
_refine_ls_number_restraints     881
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0646
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.399
_refine_ls_restrained_S_all      1.331
_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
N1 N 0.50493(9) 0.46110(9) 0.1937(4) 0.0183(6) Uani 0.9258(10) 1 d D . P A 1
C1 C 0.52841(12) 0.43515(12) 0.1226(5) 0.0239(8) Uani 0.9258(10) 1 d D . P A 1
H1 H 0.5199 0.4100 0.1097 0.029 Uiso 0.9258(10) 1 calc R U P A 1
C2 C 0.56436(12) 0.44407(13) 0.0681(5) 0.0259(8) Uani 0.9258(10) 1 d D . P A 1
H2 H 0.5805 0.4253 0.0184 0.031 Uiso 0.9258(10) 1 calc R U P A 1
C3 C 0.57659(12) 0.48060(13) 0.0869(5) 0.0274(8) Uani 0.9258(10) 1 d D . P A 1
H3 H 0.6013 0.4874 0.0498 0.033 Uiso 0.9258(10) 1 calc R U P A 1
C4 C 0.55255(12) 0.50745(13) 0.1604(6) 0.0230(8) Uani 0.9258(10) 1 d D . P A 1
H4 H 0.5607 0.5327 0.1731 0.028 Uiso 0.9258(10) 1 calc R U P A 1
C5 C 0.51654(10) 0.49731(10) 0.2152(5) 0.0191(6) Uani 0.9258(10) 1 d D . P A 1
C6 C 0.48866(10) 0.52280(10) 0.2961(5) 0.0181(7) Uani 0.9258(10) 1 d D . P A 1
C7 C 0.49508(11) 0.56144(11) 0.3211(5) 0.0211(7) Uani 0.9258(10) 1 d D . P A 1
H7 H 0.5186 0.5721 0.2876 0.025 Uiso 0.9258(10) 1 calc R U P A 1
C8 C 0.46692(12) 0.58411(12) 0.3952(6) 0.0233(8) Uani 0.9258(10) 1 d D . P A 1
H8 H 0.4714 0.6102 0.4109 0.028 Uiso 0.9258(10) 1 calc R U P A 1
C9 C 0.43255(12) 0.56920(11) 0.4462(5) 0.0225(7) Uani 0.9258(10) 1 d D . P A 1
C10 C 0.42641(11) 0.53051(11) 0.4213(5) 0.0198(7) Uani 0.9258(10) 1 d D . P A 1
H10 H 0.4029 0.5200 0.4554 0.024 Uiso 0.9258(10) 1 calc R U P A 1
C11 C 0.45400(10) 0.50715(10) 0.3480(5) 0.0178(6) Uani 0.9258(10) 1 d D . P A 1
C12 C 0.40197(13) 0.59396(12) 0.5212(7) 0.0325(9) Uani 0.9258(10) 1 d D . P A 1
H12A H 0.3867 0.6036 0.4199 0.049 Uiso 0.9258(10) 1 calc R U P A 1
H12B H 0.4132 0.6150 0.5879 0.049 Uiso 0.9258(10) 1 calc R U P A 1
H12C H 0.3861 0.5794 0.6045 0.049 Uiso 0.9258(10) 1 calc R U P A 1
Au1 Au 0.45023(2) 0.45087(2) 0.28542(2) 0.01726(6) Uani 0.9258(10) 1 d D . P A
1
C13 C 0.44672(11) 0.39554(12) 0.1977(5) 0.0238(8) Uani 0.474(3) 1 d D . P A 2
S1 S 0.4605(2) 0.35823(12) 0.3226(9) 0.0315(9) Uani 0.474(3) 1 d D U P A 2
C14 C 0.4304(8) 0.3850(4) 0.031(2) 0.029(4) Uani 0.474(3) 1 d D U P A 2
H14 H 0.4211 0.4027 -0.0551 0.035 Uiso 0.474(3) 1 calc R U P A 2
C15 C 0.4464(7) 0.3268(3) 0.150(2) 0.029(3) Uani 0.474(3) 1 d D U P A 2
C16 C 0.4486(4) 0.2869(3) 0.1529(18) 0.039(3) Uani 0.474(3) 1 d D U P A 2
H16 H 0.4590 0.2743 0.2558 0.047 Uiso 0.474(3) 1 calc R U P A 2
C17 C 0.4356(4) 0.2670(3) 0.006(2) 0.045(3) Uani 0.474(3) 1 d D U P A 2
H17 H 0.4378 0.2404 0.0044 0.053 Uiso 0.474(3) 1 calc R U P A 2
C18 C 0.4193(3) 0.2853(4) -0.1418(19) 0.041(2) Uani 0.474(3) 1 d D U P A 2
H18 H 0.4099 0.2708 -0.2414 0.049 Uiso 0.474(3) 1 calc R U P A 2
C19 C 0.4163(4) 0.3237(3) -0.1475(18) 0.034(2) Uani 0.474(3) 1 d D U P A 2
H19 H 0.4058 0.3356 -0.2520 0.041 Uiso 0.474(3) 1 calc R U P A 2
C20 C 0.4288(7) 0.3451(3) 0.001(3) 0.027(3) Uani 0.474(3) 1 d D U P A 2
C21 C 0.39890(11) 0.44414(11) 0.3898(5) 0.0223(7) Uani 0.740(3) 1 d D . P A 3
S2 S 0.35864(6) 0.45781(7) 0.2784(3) 0.0346(4) Uani 0.740(3) 1 d D U P A 3
C22 C 0.3908(3) 0.4291(5) 0.5586(18) 0.0193(17) Uani 0.740(3) 1 d D U P A 3
H22 H 0.4097 0.4196 0.6380 0.023 Uiso 0.740(3) 1 calc R U P A 3
C23 C 0.32997(18) 0.4440(2) 0.4625(11) 0.0333(14) Uani 0.740(3) 1 d D U P A 3
C24 C 0.29067(19) 0.4462(2) 0.4763(13) 0.0482(17) Uani 0.740(3) 1 d D U P A 3
H24 H 0.2762 0.4561 0.3780 0.058 Uiso 0.740(3) 1 calc R U P A 3
C25 C 0.2734(2) 0.4339(3) 0.6328(15) 0.053(2) Uani 0.740(3) 1 d D U P A 3
H25 H 0.2467 0.4350 0.6421 0.063 Uiso 0.740(3) 1 calc R U P A 3
C26 C 0.29453(18) 0.4198(2) 0.7793(12) 0.0465(16) Uani 0.740(3) 1 d D U P A 3
H26 H 0.2822 0.4120 0.8885 0.056 Uiso 0.740(3) 1 calc R U P A 3
C27 C 0.33322(17) 0.41705(19) 0.7664(10) 0.0343(13) Uani 0.740(3) 1 d D U P A 3
H27 H 0.3474 0.4072 0.8658 0.041 Uiso 0.740(3) 1 calc R U P A 3
C28 C 0.35152(17) 0.4288(3) 0.6061(10) 0.0256(12) Uani 0.740(3) 1 d D U P A 3
C13B C 0.44672(11) 0.39554(12) 0.1977(5) 0.0238(8) Uani 0.451(3) 1 d D . P A 4
S1B S 0.4285(2) 0.38724(13) -0.0124(7) 0.0275(9) Uani 0.451(3) 1 d D U P A 4
C14B C 0.4556(9) 0.3617(4) 0.286(3) 0.032(5) Uani 0.451(3) 1 d D U P A 4
H14B H 0.4667 0.3610 0.4045 0.038 Uiso 0.451(3) 1 calc R U P A 4
C15B C 0.4334(7) 0.3386(3) 0.009(2) 0.027(3) Uani 0.451(3) 1 d D U P A 4
C16B C 0.4227(4) 0.3109(3) -0.1205(17) 0.035(3) Uani 0.451(3) 1 d D U P A 4
H16B H 0.4116 0.3180 -0.2337 0.042 Uiso 0.451(3) 1 calc R U P A 4
C17B C 0.4288(4) 0.2738(3) -0.0798(16) 0.033(2) Uani 0.451(3) 1 d D U P A 4
H17B H 0.4233 0.2550 -0.1682 0.040 Uiso 0.451(3) 1 calc R U P A 4
C18B C 0.4431(5) 0.2636(3) 0.0905(18) 0.036(3) Uani 0.451(3) 1 d D U P A 4
H18B H 0.4467 0.2376 0.1164 0.044 Uiso 0.451(3) 1 calc R U P A 4
C19B C 0.4521(6) 0.2895(3) 0.2229(19) 0.032(2) Uani 0.451(3) 1 d D U P A 4
H19B H 0.4618 0.2817 0.3381 0.038 Uiso 0.451(3) 1 calc R U P A 4
C20B C 0.4465(8) 0.3280(4) 0.184(2) 0.028(3) Uani 0.451(3) 1 d D U P A 4
Au1C Au 0.43288(11) 0.45962(8) 0.3143(3) 0.0248(7) Uani 0.0742(10) 1 d D U P B
5
C13C C 0.4396(17) 0.4055(7) 0.234(5) 0.0238(8) Uani 0.0742(10) 1 d D U P B 5
S1C S 0.4529(7) 0.3698(6) 0.372(3) 0.042(4) Uani 0.0742(10) 1 d D U P B 5
C14C C 0.4255(19) 0.3918(12) 0.068(5) 0.023(9) Uani 0.0742(10) 1 d D U P B 5
H14C H 0.4136 0.4075 -0.0196 0.028 Uiso 0.0742(10) 1 calc R U P B 5
C15C C 0.443(2) 0.3357(8) 0.207(6) 0.029(3) Uani 0.0742(10) 1 d D U P B 5
C16C C 0.450(4) 0.2967(9) 0.220(9) 0.039(3) Uani 0.0742(10) 1 d D U P B 5
H16C H 0.4605 0.2864 0.3286 0.047 Uiso 0.0742(10) 1 calc R U P B 5
C17C C 0.442(3) 0.2740(11) 0.075(9) 0.040(14) Uani 0.0742(10) 1 d D U P B 5
H17C H 0.4453 0.2476 0.0833 0.048 Uiso 0.0742(10) 1 calc R U P B 5
C18C C 0.428(2) 0.2898(14) -0.086(8) 0.038(12) Uani 0.0742(10) 1 d D U P B 5
H18C H 0.4202 0.2737 -0.1836 0.046 Uiso 0.0742(10) 1 calc R U P B 5
C19C C 0.424(2) 0.3280(15) -0.108(6) 0.033(12) Uani 0.0742(10) 1 d D U P B 5
H19C H 0.4177 0.3381 -0.2241 0.040 Uiso 0.0742(10) 1 calc R U P B 5
C20C C 0.431(2) 0.3520(11) 0.041(5) 0.029(10) Uani 0.0742(10) 1 d D U P B 5
C21C C 0.3808(7) 0.4476(16) 0.424(5) 0.029(6) Uani 0.0742(10) 1 d D U P B 5
S2C S 0.3391(5) 0.4548(5) 0.318(2) 0.035(3) Uani 0.0742(10) 1 d D U P B 5
C22C C 0.3759(9) 0.4301(14) 0.593(5) 0.021(7) Uani 0.0742(10) 1 d D U P B 5
H22C H 0.3963 0.4207 0.6633 0.025 Uiso 0.0742(10) 1 calc R U P B 5
C23C C 0.3136(7) 0.4410(14) 0.511(4) 0.025(8) Uani 0.0742(10) 1 d D U P B 5
C24C C 0.2752(8) 0.4466(16) 0.550(5) 0.021(9) Uani 0.0742(10) 1 d D U P B 5
H24C H 0.2603 0.4618 0.4717 0.026 Uiso 0.0742(10) 1 calc R U P B 5
C25C C 0.2592(9) 0.430(2) 0.701(7) 0.053(19) Uani 0.0742(10) 1 d D U P B 5
H25C H 0.2327 0.4284 0.7124 0.064 Uiso 0.0742(10) 1 calc R U P B 5
C26C C 0.2828(10) 0.4162(18) 0.837(6) 0.034(12) Uani 0.0742(10) 1 d D U P B 5
H26C H 0.2722 0.4045 0.9419 0.040 Uiso 0.0742(10) 1 calc R U P B 5
C27C C 0.3212(10) 0.4190(15) 0.822(4) 0.024(8) Uani 0.0742(10) 1 d D U P B 5
H27C H 0.3366 0.4153 0.9263 0.028 Uiso 0.0742(10) 1 calc R U P B 5
C28C C 0.3375(9) 0.4273(16) 0.652(4) 0.028(10) Uani 0.0742(10) 1 d D U P B 5
N1C N 0.4350(8) 0.5168(5) 0.380(5) 0.023(6) Uani 0.0742(10) 1 d D U P B 5
C1C C 0.4046(10) 0.5357(10) 0.440(8) 0.036(10) Uani 0.0742(10) 1 d D U P B 5
H1C H 0.3817 0.5227 0.4623 0.044 Uiso 0.0742(10) 1 calc R U P B 5
C2C C 0.4068(11) 0.5740(10) 0.469(8) 0.035(9) Uani 0.0742(10) 1 d D U P B 5
H2C H 0.3859 0.5875 0.5163 0.042 Uiso 0.0742(10) 1 calc R U P B 5
C3C C 0.4397(11) 0.5920(9) 0.428(7) 0.032(8) Uani 0.0742(10) 1 d D U P B 5
H3C H 0.4409 0.6186 0.4388 0.039 Uiso 0.0742(10) 1 calc R U P B 5
C4C C 0.4715(11) 0.5725(8) 0.371(8) 0.026(8) Uani 0.0742(10) 1 d D U P B 5
H4C H 0.4950 0.5848 0.3563 0.031 Uiso 0.0742(10) 1 calc R U P B 5
C5C C 0.4676(8) 0.5341(7) 0.335(6) 0.022(6) Uani 0.0742(10) 1 d D U P B 5
C6C C 0.4973(8) 0.5099(8) 0.261(6) 0.0191(6) Uani 0.0742(10) 1 d D U P B 5
C7C C 0.5342(8) 0.5218(9) 0.226(6) 0.0230(8) Uani 0.0742(10) 1 d D U P B 5
H7C H 0.5417 0.5465 0.2596 0.028 Uiso 0.0742(10) 1 calc R U P B 5
C8C C 0.5598(11) 0.4975(10) 0.142(10) 0.027(10) Uani 0.0742(10) 1 d D U P B 5
H8C H 0.5836 0.5067 0.1033 0.032 Uiso 0.0742(10) 1 calc R U P B 5
C9C C 0.5505(9) 0.4603(10) 0.117(7) 0.031(8) Uani 0.0742(10) 1 d D U P B 5
C10C C 0.5149(9) 0.4476(9) 0.171(6) 0.022(7) Uani 0.0742(10) 1 d D U P B 5
H10C H 0.5096 0.4214 0.1636 0.027 Uiso 0.0742(10) 1 calc R U P B 5
C11C C 0.4874(7) 0.4717(8) 0.236(6) 0.025(7) Uani 0.0742(10) 1 d D U P B 5
C12C C 0.5785(14) 0.4332(14) 0.040(10) 0.042(12) Uani 0.0742(10) 1 d D U P B 5
H12D H 0.5686 0.4221 -0.0729 0.063 Uiso 0.0742(10) 1 calc R U P B 5
H12E H 0.5832 0.4133 0.1299 0.063 Uiso 0.0742(10) 1 calc R U P B 5
H12F H 0.6020 0.4465 0.0134 0.063 Uiso 0.0742(10) 1 calc R U P B 5
C21B C 0.39890(11) 0.44414(11) 0.3898(5) 0.0223(7) Uani 0.186(3) 1 d D . P A 6
S2B S 0.3922(4) 0.4256(7) 0.593(2) 0.033(3) Uani 0.186(3) 1 d D U P A 6
C22B C 0.3657(5) 0.4510(15) 0.292(4) 0.054(11) Uani 0.186(3) 1 d D U P A 6
H22A H 0.3652 0.4584 0.1672 0.065 Uiso 0.186(3) 1 calc R U P A 6
C23B C 0.3435(5) 0.4324(12) 0.577(3) 0.033(6) Uani 0.186(3) 1 d D U P A 6
C24B C 0.3172(6) 0.4229(9) 0.714(3) 0.051(6) Uani 0.186(3) 1 d D U P A 6
H24B H 0.3249 0.4106 0.8237 0.061 Uiso 0.186(3) 1 calc R U P A 6
C25B C 0.2802(6) 0.4318(13) 0.687(4) 0.045(7) Uani 0.186(3) 1 d D U P A 6
H25B H 0.2627 0.4320 0.7850 0.054 Uiso 0.186(3) 1 calc R U P A 6
C26B C 0.2691(6) 0.4406(11) 0.508(4) 0.057(9) Uani 0.186(3) 1 d D U P A 6
H26B H 0.2432 0.4386 0.4768 0.068 Uiso 0.186(3) 1 calc R U P A 6
C27B C 0.2940(5) 0.4521(9) 0.375(3) 0.048(6) Uani 0.186(3) 1 d D U P A 6
H27B H 0.2853 0.4642 0.2668 0.058 Uiso 0.186(3) 1 calc R U P A 6
C28B C 0.3326(5) 0.4456(12) 0.402(3) 0.033(6) Uani 0.186(3) 1 d D U P A 6


_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
N1 C1 1.349(5) . ?
N1 C5 1.361(5) . ?
N1 Au1 2.089(3) . ?
C1 C2 1.376(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.467(5) . ?
C6 C11 1.405(5) . ?
C6 C7 1.405(5) . ?
C7 C8 1.395(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(5) . ?
C9 C12 1.502(6) . ?
C10 C11 1.393(5) . ?
C10 H10 0.9500 . ?
C11 Au1 2.057(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
Au1 C21 1.992(4) . ?
Au1 C13 2.073(4) . ?
C13 C14 1.399(14) . ?
C13 S1 1.683(6) . ?
S1 C15 1.758(12) . ?
C14 C20 1.435(16) . ?
C14 H14 0.9500 . ?
C15 C20 1.410(12) . ?
C15 C16 1.423(13) . ?
C16 C17 1.367(13) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(14) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.400(13) . ?
C19 H19 0.9500 . ?
C21 C22 1.373(11) . ?
C21 S2 1.717(4) . ?
S2 C23 1.757(8) . ?
C22 C28 1.441(12) . ?
C22 H22 0.9500 . ?
C23 C24 1.404(8) . ?
C23 C28 1.406(8) . ?
C24 C25 1.369(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.401(11) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.403(8) . ?
C27 H27 0.9500 . ?
S1B C15B 1.746(12) . ?
C14B C20B 1.446(17) . ?
C14B H14B 0.9500 . ?
C15B C20B 1.413(12) . ?
C15B C16B 1.416(13) . ?
C16B C17B 1.372(12) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.390(13) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.375(12) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.411(13) . ?
C19B H19B 0.9500 . ?
Au1C C13C 2.02(3) . ?
Au1C C21C 2.06(3) . ?
Au1C C11C 2.066(18) . ?
Au1C N1C 2.090(18) . ?
C13C C14C 1.398(18) . ?
C13C S1C 1.690(16) . ?
S1C C15C 1.744(17) . ?
C14C C20C 1.440(19) . ?
C14C H14C 0.9500 . ?
C15C C16C 1.412(17) . ?
C15C C20C 1.415(16) . ?
C16C C17C 1.366(17) . ?
C16C H16C 0.9500 . ?
C17C C18C 1.393(18) . ?
C17C H17C 0.9500 . ?
C18C C19C 1.373(17) . ?
C18C H18C 0.9500 . ?
C19C C20C 1.401(17) . ?
C19C H19C 0.9500 . ?
C21C C22C 1.393(18) . ?
C21C S2C 1.691(16) . ?
S2C C23C 1.743(16) . ?
C22C C28C 1.435(19) . ?
C22C H22C 0.9500 . ?
C23C C24C 1.411(17) . ?
C23C C28C 1.422(16) . ?
C24C C25C 1.368(17) . ?
C24C H24C 0.9500 . ?
C25C C26C 1.393(18) . ?
C25C H25C 0.9500 . ?
C26C C27C 1.371(17) . ?
C26C H26C 0.9500 . ?
C27C C28C 1.400(17) . ?
C27C H27C 0.9500 . ?
N1C C1C 1.348(19) . ?
N1C C5C 1.353(18) . ?
C1C C2C 1.38(2) . ?
C1C H1C 0.9500 . ?
C2C C3C 1.37(2) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.39(2) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.398(19) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.466(18) . ?
C6C C7C 1.401(18) . ?
C6C C11C 1.417(18) . ?
C7C C8C 1.40(2) . ?
C7C H7C 0.9500 . ?
C8C C9C 1.377(19) . ?
C8C H8C 0.9500 . ?
C9C C10C 1.401(19) . ?
C9C C12C 1.495(19) . ?
C10C C11C 1.385(19) . ?
C10C H10C 0.9500 . ?
C12C H12D 0.9800 . ?
C12C H12E 0.9800 . ?
C12C H12F 0.9800 . ?
S2B C23B 1.754(16) . ?
C22B C28B 1.440(18) . ?
C22B H22A 0.9500 . ?
C23B C24B 1.414(16) . ?
C23B C28B 1.414(15) . ?
C24B C25B 1.368(17) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.398(18) . ?
C25B H25B 0.9500 . ?
C26B C27B 1.376(16) . ?
C26B H26B 0.9500 . ?
C27B C28B 1.405(16) . ?
C27B H27B 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 N1 C5 120.3(3) . . ?
C1 N1 Au1 125.5(3) . . ?
C5 N1 Au1 114.2(3) . . ?
N1 C1 C2 121.9(4) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 118.8(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 119.5(4) . . ?
N1 C5 C6 115.2(3) . . ?
C4 C5 C6 125.3(4) . . ?
C11 C6 C7 119.7(3) . . ?
C11 C6 C5 117.2(3) . . ?
C7 C6 C5 123.1(3) . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 118.5(4) . . ?
C8 C9 C12 120.8(4) . . ?
C10 C9 C12 120.6(4) . . ?
C11 C10 C9 121.6(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C6 119.0(3) . . ?
C10 C11 Au1 128.3(3) . . ?
C6 C11 Au1 112.5(3) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 Au1 N1 80.84(14) . . ?
C14 C13 S1 112.3(7) . . ?
C13 S1 C15 91.7(6) . . ?
C13 C14 C20 114.4(12) . . ?
C13 C14 H14 122.8 . . ?
C20 C14 H14 122.8 . . ?
C20 C15 C16 119.9(11) . . ?
C20 C15 S1 112.6(10) . . ?
C16 C15 S1 127.3(10) . . ?
C17 C16 C15 118.9(11) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 120.7(10) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 121.6(10) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 119.7(11) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C15 119.0(11) . . ?
C19 C20 C14 132.0(12) . . ?
C15 C20 C14 108.8(12) . . ?
C22 C21 S2 111.2(5) . . ?
C21 S2 C23 92.5(3) . . ?
C21 C22 C28 114.9(9) . . ?
C21 C22 H22 122.6 . . ?
C28 C22 H22 122.6 . . ?
C24 C23 C28 120.7(7) . . ?
C24 C23 S2 128.1(6) . . ?
C28 C23 S2 111.1(5) . . ?
C25 C24 C23 119.3(7) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.7(6) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C27 C26 C25 120.5(7) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 119.8(7) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C23 118.9(6) . . ?
C27 C28 C22 130.7(7) . . ?
C23 C28 C22 110.3(7) . . ?
C20B C14B H14B 122.4 . . ?
C20B C15B C16B 120.5(11) . . ?
C20B C15B S1B 112.2(10) . . ?
C16B C15B S1B 127.0(10) . . ?
C17B C16B C15B 118.9(10) . . ?
C17B C16B H16B 120.6 . . ?
C15B C16B H16B 120.6 . . ?
C16B C17B C18B 120.2(10) . . ?
C16B C17B H17B 119.9 . . ?
C18B C17B H17B 119.9 . . ?
C19B C18B C17B 122.5(10) . . ?
C19B C18B H18B 118.7 . . ?
C17B C18B H18B 118.7 . . ?
C18B C19B C20B 118.6(11) . . ?
C18B C19B H19B 120.7 . . ?
C20B C19B H19B 120.7 . . ?
C19B C20B C15B 119.0(11) . . ?
C19B C20B C14B 132.1(13) . . ?
C15B C20B C14B 108.5(12) . . ?
C13C Au1C C21C 91(2) . . ?
C13C Au1C C11C 90.4(19) . . ?
C21C Au1C C11C 173.2(16) . . ?
C13C Au1C N1C 170.4(19) . . ?
C21C Au1C N1C 98.4(18) . . ?
C11C Au1C N1C 80.1(10) . . ?
C14C C13C S1C 110.7(15) . . ?
C14C C13C Au1C 123(2) . . ?
S1C C13C Au1C 125.2(19) . . ?
C13C S1C C15C 93.1(11) . . ?
C13C C14C C20C 114.8(18) . . ?
C13C C14C H14C 122.6 . . ?
C20C C14C H14C 122.6 . . ?
C16C C15C C20C 121.0(18) . . ?
C16C C15C S1C 127.0(19) . . ?
C20C C15C S1C 111.7(15) . . ?
C17C C16C C15C 119(2) . . ?
C17C C16C H16C 120.3 . . ?
C15C C16C H16C 120.3 . . ?
C16C C17C C18C 120(2) . . ?
C16C C17C H17C 120.2 . . ?
C18C C17C H17C 120.2 . . ?
C19C C18C C17C 122(2) . . ?
C19C C18C H18C 119.1 . . ?
C17C C18C H18C 119.1 . . ?
C18C C19C C20C 120(2) . . ?
C18C C19C H19C 120.0 . . ?
C20C C19C H19C 120.0 . . ?
C19C C20C C15C 117.7(18) . . ?
C19C C20C C14C 133(2) . . ?
C15C C20C C14C 108.9(17) . . ?
C22C C21C S2C 111.1(15) . . ?
C22C C21C Au1C 123.3(16) . . ?
S2C C21C Au1C 125.4(15) . . ?
C21C S2C C23C 92.6(11) . . ?
C21C C22C C28C 114.6(18) . . ?
C21C C22C H22C 122.7 . . ?
C28C C22C H22C 122.7 . . ?
C24C C23C C28C 118.6(18) . . ?
C24C C23C S2C 129.0(17) . . ?
C28C C23C S2C 111.7(14) . . ?
C25C C24C C23C 120(2) . . ?
C25C C24C H24C 119.8 . . ?
C23C C24C H24C 119.8 . . ?
C24C C25C C26C 118(2) . . ?
C24C C25C H25C 120.8 . . ?
C26C C25C H25C 120.8 . . ?
C27C C26C C25C 121(2) . . ?
C27C C26C H26C 119.5 . . ?
C25C C26C H26C 119.5 . . ?
C26C C27C C28C 120(2) . . ?
C26C C27C H27C 120.0 . . ?
C28C C27C H27C 120.0 . . ?
C27C C28C C23C 117.8(18) . . ?
C27C C28C C22C 132(2) . . ?
C23C C28C C22C 109.1(16) . . ?
C1C N1C C5C 123(2) . . ?
C1C N1C Au1C 122(2) . . ?
C5C N1C Au1C 114.7(16) . . ?
N1C C1C C2C 120(2) . . ?
N1C C1C H1C 120.1 . . ?
C2C C1C H1C 120.1 . . ?
C3C C2C C1C 119(2) . . ?
C3C C2C H2C 120.7 . . ?
C1C C2C H2C 120.7 . . ?
C2C C3C C4C 122(2) . . ?
C2C C3C H3C 119.1 . . ?
C4C C3C H3C 119.1 . . ?
C3C C4C C5C 118(2) . . ?
C3C C4C H4C 121.2 . . ?
C5C C4C H4C 121.2 . . ?
N1C C5C C4C 119.0(19) . . ?
N1C C5C C6C 116.1(19) . . ?
C4C C5C C6C 125(2) . . ?
C7C C6C C11C 120.1(18) . . ?
C7C C6C C5C 124(2) . . ?
C11C C6C C5C 115.5(18) . . ?
C8C C7C C6C 120(2) . . ?
C8C C7C H7C 119.9 . . ?
C6C C7C H7C 119.9 . . ?
C9C C8C C7C 120(2) . . ?
C9C C8C H8C 120.1 . . ?
C7C C8C H8C 120.1 . . ?
C8C C9C C10C 119(2) . . ?
C8C C9C C12C 121(2) . . ?
C10C C9C C12C 120(2) . . ?
C11C C10C C9C 122(2) . . ?
C11C C10C H10C 118.8 . . ?
C9C C10C H10C 118.8 . . ?
C10C C11C C6C 117.4(18) . . ?
C10C C11C Au1C 129.1(19) . . ?
C6C C11C Au1C 113.4(15) . . ?
C9C C12C H12D 109.5 . . ?
C9C C12C H12E 109.5 . . ?
H12D C12C H12E 109.5 . . ?
C9C C12C H12F 109.5 . . ?
H12D C12C H12F 109.5 . . ?
H12E C12C H12F 109.5 . . ?
C28B C22B H22A 123.7 . . ?
C24B C23B C28B 122.5(15) . . ?
C24B C23B S2B 125.1(15) . . ?
C28B C23B S2B 112.2(13) . . ?
C25B C24B C23B 118.4(18) . . ?
C25B C24B H24B 120.8 . . ?
C23B C24B H24B 120.8 . . ?
C24B C25B C26B 117.5(18) . . ?
C24B C25B H25B 121.2 . . ?
C26B C25B H25B 121.2 . . ?
C27B C26B C25B 122.8(19) . . ?
C27B C26B H26B 118.6 . . ?
C25B C26B H26B 118.6 . . ?
C26B C27B C28B 118.7(18) . . ?
C26B C27B H27B 120.7 . . ?
C28B C27B H27B 120.7 . . ?
C27B C28B C23B 116.8(15) . . ?
C27B C28B C22B 134.4(17) . . ?
C23B C28B C22B 108.8(15) . . ?

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
C5 N1 C1 C2 -0.6(5) . . . . ?
Au1 N1 C1 C2 -178.8(3) . . . . ?
N1 C1 C2 C3 -0.1(6) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C1 N1 C5 C4 1.1(5) . . . . ?
Au1 N1 C5 C4 179.6(3) . . . . ?
C1 N1 C5 C6 -179.2(3) . . . . ?
Au1 N1 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 N1 -1.0(6) . . . . ?
C3 C4 C5 C6 179.4(4) . . . . ?
N1 C5 C6 C11 2.2(5) . . . . ?
C4 C5 C6 C11 -178.2(4) . . . . ?
N1 C5 C6 C7 -177.1(3) . . . . ?
C4 C5 C6 C7 2.5(6) . . . . ?
C11 C6 C7 C8 -0.7(5) . . . . ?
C5 C6 C7 C8 178.5(3) . . . . ?
C6 C7 C8 C9 0.4(6) . . . . ?
C7 C8 C9 C10 -0.2(6) . . . . ?
C7 C8 C9 C12 -178.3(4) . . . . ?
C8 C9 C10 C11 0.3(6) . . . . ?
C12 C9 C10 C11 178.4(4) . . . . ?
C9 C10 C11 C6 -0.6(5) . . . . ?
C9 C10 C11 Au1 -176.0(3) . . . . ?
C7 C6 C11 C10 0.8(5) . . . . ?
C5 C6 C11 C10 -178.5(3) . . . . ?
C7 C6 C11 Au1 176.9(3) . . . . ?
C5 C6 C11 Au1 -2.4(4) . . . . ?
C14 C13 S1 C15 2.3(17) . . . . ?
Au1 C13 S1 C15 178.6(9) . . . . ?
S1 C13 C14 C20 0(3) . . . . ?
Au1 C13 C14 C20 -176.5(16) . . . . ?
C13 S1 C15 C20 -4.0(18) . . . . ?
C13 S1 C15 C16 -179(2) . . . . ?
C20 C15 C16 C17 4(3) . . . . ?
S1 C15 C16 C17 179.0(16) . . . . ?
C15 C16 C17 C18 -2(2) . . . . ?
C16 C17 C18 C19 1(2) . . . . ?
C17 C18 C19 C20 -2(2) . . . . ?
C18 C19 C20 C15 4(3) . . . . ?
C18 C19 C20 C14 178(3) . . . . ?
C16 C15 C20 C19 -5(3) . . . . ?
S1 C15 C20 C19 179.5(19) . . . . ?
C16 C15 C20 C14 -180(2) . . . . ?
S1 C15 C20 C14 4(3) . . . . ?
C13 C14 C20 C19 -177(2) . . . . ?
C13 C14 C20 C15 -3(3) . . . . ?
C22 C21 S2 C23 1.0(10) . . . . ?
Au1 C21 S2 C23 -177.6(4) . . . . ?
S2 C21 C22 C28 -1.3(18) . . . . ?
Au1 C21 C22 C28 177.3(9) . . . . ?
C21 S2 C23 C24 -179.7(8) . . . . ?
C21 S2 C23 C28 -0.5(6) . . . . ?
C28 C23 C24 C25 1.0(13) . . . . ?
S2 C23 C24 C25 -179.9(8) . . . . ?
C23 C24 C25 C26 1.0(15) . . . . ?
C24 C25 C26 C27 -1.8(15) . . . . ?
C25 C26 C27 C28 0.7(12) . . . . ?
C26 C27 C28 C23 1.3(11) . . . . ?
C26 C27 C28 C22 179.8(14) . . . . ?
C24 C23 C28 C27 -2.1(12) . . . . ?
S2 C23 C28 C27 178.6(7) . . . . ?
C24 C23 C28 C22 179.1(12) . . . . ?
S2 C23 C28 C22 -0.1(12) . . . . ?
C21 C22 C28 C27 -177.6(9) . . . . ?
C21 C22 C28 C23 0.9(19) . . . . ?
C20B C15B C16B C17B -6(3) . . . . ?
S1B C15B C16B C17B 179.9(16) . . . . ?
C15B C16B C17B C18B 4(2) . . . . ?
C16B C17B C18B C19B -1(2) . . . . ?
C17B C18B C19B C20B 0(3) . . . . ?
C18B C19B C20B C15B -2(3) . . . . ?
C18B C19B C20B C14B -175(3) . . . . ?
C16B C15B C20B C19B 5(3) . . . . ?
S1B C15B C20B C19B -180(2) . . . . ?
C16B C15B C20B C14B 179(2) . . . . ?
S1B C15B C20B C14B -6(3) . . . . ?
C14C C13C S1C C15C 4(6) . . . . ?
Au1C C13C S1C C15C 170(4) . . . . ?
S1C C13C C14C C20C -9(8) . . . . ?
Au1C C13C C14C C20C -176(5) . . . . ?
C13C S1C C15C C16C 175(9) . . . . ?
C13C S1C C15C C20C 2(7) . . . . ?
C20C C15C C16C C17C -5(16) . . . . ?
S1C C15C C16C C17C -178(9) . . . . ?
C15C C16C C17C C18C 2(18) . . . . ?
C16C C17C C18C C19C 4(16) . . . . ?
C17C C18C C19C C20C -8(13) . . . . ?
C18C C19C C20C C15C 5(11) . . . . ?
C18C C19C C20C C14C -172(8) . . . . ?
C16C C15C C20C C19C 2(12) . . . . ?
S1C C15C C20C C19C 176(6) . . . . ?
C16C C15C C20C C14C 179(9) . . . . ?
S1C C15C C20C C14C -7(8) . . . . ?
C13C C14C C20C C19C -173(8) . . . . ?
C13C C14C C20C C15C 10(9) . . . . ?
C22C C21C S2C C23C 8(5) . . . . ?
Au1C C21C S2C C23C -175(4) . . . . ?
S2C C21C C22C C28C -9(6) . . . . ?
Au1C C21C C22C C28C 175(4) . . . . ?
C21C S2C C23C C24C 165(6) . . . . ?
C21C S2C C23C C28C -6(5) . . . . ?
C28C C23C C24C C25C -17(9) . . . . ?
S2C C23C C24C C25C 173(6) . . . . ?
C23C C24C C25C C26C 16(11) . . . . ?
C24C C25C C26C C27C 1(12) . . . . ?
C25C C26C C27C C28C -16(10) . . . . ?
C26C C27C C28C C23C 14(8) . . . . ?
C26C C27C C28C C22C -176(6) . . . . ?
C24C C23C C28C C27C 2(8) . . . . ?
S2C C23C C28C C27C 173(4) . . . . ?
C24C C23C C28C C22C -170(5) . . . . ?
S2C C23C C28C C22C 2(6) . . . . ?
C21C C22C C28C C27C -165(6) . . . . ?
C21C C22C C28C C23C 5(7) . . . . ?
C5C N1C C1C C2C -4(9) . . . . ?
Au1C N1C C1C C2C -175(4) . . . . ?
N1C C1C C2C C3C 3(9) . . . . ?
C1C C2C C3C C4C -5(9) . . . . ?
C2C C3C C4C C5C 7(8) . . . . ?
C1C N1C C5C C4C 7(7) . . . . ?
Au1C N1C C5C C4C 179(4) . . . . ?
C1C N1C C5C C6C -176(5) . . . . ?
Au1C N1C C5C C6C -5(5) . . . . ?
C3C C4C C5C N1C -9(7) . . . . ?
C3C C4C C5C C6C 175(5) . . . . ?
N1C C5C C6C C7C -172(4) . . . . ?
C4C C5C C6C C7C 4(8) . . . . ?
N1C C5C C6C C11C 3(6) . . . . ?
C4C C5C C6C C11C 180(5) . . . . ?
C11C C6C C7C C8C 9(8) . . . . ?
C5C C6C C7C C8C -175(5) . . . . ?
C6C C7C C8C C9C -9(9) . . . . ?
C7C C8C C9C C10C 1(10) . . . . ?
C7C C8C C9C C12C -175(6) . . . . ?
C8C C9C C10C C11C 6(8) . . . . ?
C12C C9C C10C C11C -177(5) . . . . ?
C9C C10C C11C C6C -5(8) . . . . ?
C9C C10C C11C Au1C 177(4) . . . . ?
C7C C6C C11C C10C -2(7) . . . . ?
C5C C6C C11C C10C -178(4) . . . . ?
C7C C6C C11C Au1C 176(3) . . . . ?
C5C C6C C11C Au1C -1(5) . . . . ?
C28B C23B C24B C25B -9(6) . . . . ?
S2B C23B C24B C25B 176(4) . . . . ?
C23B C24B C25B C26B 16(6) . . . . ?
C24B C25B C26B C27B -21(6) . . . . ?
C25B C26B C27B C28B 17(6) . . . . ?
C26B C27B C28B C23B -9(5) . . . . ?
C26B C27B C28B C22B 175(5) . . . . ?
C24B C23B C28B C27B 5(6) . . . . ?
S2B C23B C28B C27B -180(3) . . . . ?
C24B C23B C28B C22B -177(4) . . . . ?
S2B C23B C28B C22B -3(5) . . . . ?

_refine_diff_density_max         1.002
_refine_diff_density_min         -0.992
_refine_diff_density_rms         0.110

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1009038'
#######################################################################
#
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#                                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
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# 
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#  data retrieval see:
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data_Quest14mz091_0m_twin

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 Au N'
_chemical_formula_weight         547.43

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5722(7)
_cell_length_b                   16.2301(14)
_cell_length_c                   16.7076(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.349(4)
_cell_angle_gamma                90
_cell_volume                     2049.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      2.4361
_cell_measurement_theta_max      31.3175

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    7.188
_shelx_estimated_absorpt_T_min   0.327
_shelx_estimated_absorpt_T_max   0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4199
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'Apex2 v2014.1-1 (Bruker, 2014)'

_exptl_special_details           
; 
The crystal under investigation was found to be non-merohedrally 
twinned. The orientation matrices for the two components were 
identified using the program Cell_Now, with the two components 
being related by a 180 degree rotation around the reciprocal 
c-axis. The two components were initially integrated using Saint 
and corrected for absorption using twinabs.


The exact twin matrix identified by the integration program was 
found to be 

-0.99994 -0.00155  0.00043
 0.00707 -0.99999 -0.00013
 0.25079  0.00006  0.99995 


Integration proofed problematic due to excessive multiple overlap
of reflections, resulting in large numbers of rejected reflections.
Attempts were made to adjust integration parameters to avoid excessive
rejections (through adjustments to integration queue size, blending of
profiles, integration box slicing and twin overlap parameters), which
led to less but still substantial numbers of rejected reflections.
With no complete data set obtainable through simultaneous integration
of both twin domains, the data were instead handled as if not twinned,
with only the major domain integrated, and converted into an hklf 5
type format hkl file after integration using the "Make HKLF5 File"
routine as implemented in WinGX. The twin law matrix was used as
obtained from SAINT, see above. The Overlap R1 and R2 values used
were 0.41, i.e. reflections with a discriminator function less or
equal to overlap radius of 0.41 were counted overlapped, all others
as single. The discriminator function used was the "delta function
on index non-integrality". No reflections were omitted.

The structure was solved using direct methods with the hklf 4 type
file and was refined using the hklf 5 type file, resulting in a BASF
value of 0.150(2).

A refinement using the incomplete data obtained through SAINT and
TWINABS gave similar refinement statistics, but with higher overall
R values and with less well defined ADPs (several atoms NPD or close 
to NPD).

No Rint value is obtainable for the hklf 5 type file using the WinGX
routine. The value from a refinement with the uncorrected hklf 4 type 
file is given instead. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16310
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.442
_diffrn_reflns_theta_max         31.674
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             16310
_reflns_number_gt                13718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'Apex2 v2014.1-1 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev645 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+90.5211P] 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         16310
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.1750
_refine_ls_wR_factor_gt          0.1635
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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_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 0.2489(18) 0.5763(8) 0.6926(7) 0.024(3) Uani 1 1 d . . . . .
H1 H 0.2179 0.5571 0.7437 0.029 Uiso 1 1 calc R U . . .
C2 C 0.3103(19) 0.6575(9) 0.6854(8) 0.028(3) Uani 1 1 d . . . . .
H2 H 0.3259 0.6922 0.7311 0.033 Uiso 1 1 calc R U . . .
C3 C 0.347(2) 0.6855(9) 0.6100(9) 0.031(3) Uani 1 1 d . . . . .
H3 H 0.3883 0.7403 0.6033 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3244(18) 0.6343(8) 0.5452(8) 0.024(3) Uani 1 1 d . . . . .
H4 H 0.3472 0.6540 0.4933 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2671(16) 0.5523(8) 0.5552(7) 0.019(2) Uani 1 1 d . . . . .
C6 C 0.2446(17) 0.4911(8) 0.4919(7) 0.020(2) Uani 1 1 d . . . . .
C7 C 0.2751(18) 0.5078(8) 0.4111(7) 0.024(3) Uani 1 1 d . . . . .
H7 H 0.3154 0.5607 0.3962 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2467(19) 0.4476(8) 0.3534(7) 0.027(3) Uani 1 1 d . . . . .
H8 H 0.2700 0.4593 0.2993 0.032 Uiso 1 1 calc R U . . .
C9 C 0.1847(18) 0.3703(9) 0.3731(8) 0.025(3) Uani 1 1 d . . . . .
C10 C 0.1538(17) 0.3540(8) 0.4532(7) 0.020(2) Uani 1 1 d . . . . .
H10 H 0.1097 0.3015 0.4671 0.024 Uiso 1 1 calc R U . . .
C11 C 0.1853(16) 0.4118(8) 0.5123(6) 0.018(2) Uani 1 1 d . . . . .
C12 C 0.154(2) 0.3037(10) 0.3115(8) 0.034(3) Uani 1 1 d . . . . .
H12A H 0.1022 0.3278 0.2617 0.051 Uiso 1 1 calc R U . . .
H12B H 0.0733 0.2624 0.3315 0.051 Uiso 1 1 calc R U . . .
H12C H 0.2672 0.2775 0.3011 0.051 Uiso 1 1 calc R U . . .
C13 C 0.1414(17) 0.3973(9) 0.7588(6) 0.022(2) Uani 1 1 d . . . . .
C14 C -0.0237(17) 0.3996(10) 0.7929(7) 0.026(3) Uani 1 1 d . . . . .
H14 H -0.1282 0.3967 0.7587 0.032 Uiso 1 1 calc R U . . .
C15 C -0.039(2) 0.4060(10) 0.8750(8) 0.033(3) Uani 1 1 d . . . . .
H15 H -0.1523 0.4070 0.8966 0.040 Uiso 1 1 calc R U . . .
C16 C 0.1136(19) 0.4110(10) 0.9255(8) 0.031(3) Uani 1 1 d . . . . .
H16 H 0.1052 0.4164 0.9818 0.038 Uiso 1 1 calc R U . . .
C17 C 0.2747(19) 0.4081(8) 0.8937(8) 0.027(3) Uani 1 1 d . . . . .
H17 H 0.3781 0.4107 0.9287 0.032 Uiso 1 1 calc R U . . .
C18 C 0.2932(18) 0.4014(9) 0.8106(7) 0.026(3) Uani 1 1 d . . . . .
C19 C 0.4748(18) 0.4034(11) 0.7788(8) 0.033(3) Uani 1 1 d . . . . .
H19A H 0.4927 0.4563 0.7522 0.049 Uiso 1 1 calc R U . . .
H19B H 0.4862 0.3585 0.7403 0.049 Uiso 1 1 calc R U . . .
H19C H 0.5639 0.3968 0.8233 0.049 Uiso 1 1 calc R U . . .
C20 C 0.094(2) 0.2775(7) 0.6262(7) 0.023(3) Uani 1 1 d . . . . .
C21 C -0.0766(19) 0.2525(9) 0.6346(8) 0.027(3) Uani 1 1 d . . . . .
H21 H -0.1630 0.2919 0.6477 0.033 Uiso 1 1 calc R U . . .
C22 C -0.126(2) 0.1692(10) 0.6242(9) 0.034(3) Uani 1 1 d . . . . .
H22 H -0.2444 0.1528 0.6318 0.041 Uiso 1 1 calc R U . . .
C23 C -0.003(2) 0.1109(9) 0.6027(8) 0.037(4) Uani 1 1 d . . . . .
H23 H -0.0360 0.0553 0.5922 0.045 Uiso 1 1 calc R U . . .
C24 C 0.172(2) 0.1366(9) 0.5972(8) 0.031(3) Uani 1 1 d . . . . .
H24 H 0.2590 0.0966 0.5868 0.037 Uiso 1 1 calc R U . . .
C25 C 0.224(2) 0.2205(8) 0.6064(8) 0.025(3) Uani 1 1 d . . . . .
C26 C 0.409(2) 0.2424(10) 0.5965(10) 0.037(4) Uani 1 1 d . . . . .
H26A H 0.4549 0.2733 0.6436 0.056 Uiso 1 1 calc R U . . .
H26B H 0.4163 0.2765 0.5484 0.056 Uiso 1 1 calc R U . . .
H26C H 0.4784 0.1921 0.5909 0.056 Uiso 1 1 calc R U . . .
N1 N 0.2329(14) 0.5250(6) 0.6298(6) 0.0166(19) Uani 1 1 d . . . . .
Au1 Au 0.15839(7) 0.39981(3) 0.63484(3) 0.01958(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 N1 1.339(15) . ?
C1 C2 1.405(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.368(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.413(17) . ?
C4 H4 0.9500 . ?
C5 N1 1.362(14) . ?
C5 C6 1.454(17) . ?
C6 C7 1.410(15) . ?
C6 C11 1.411(17) . ?
C7 C8 1.380(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(17) . ?
C9 C12 1.501(18) . ?
C10 C11 1.374(16) . ?
C10 H10 0.9500 . ?
C11 Au1 2.078(10) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.400(19) . ?
C13 C14 1.405(17) . ?
C13 Au1 2.083(10) . ?
C14 C15 1.387(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.39(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.360(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.407(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.503(19) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.37(2) . ?
C20 C25 1.404(18) . ?
C20 Au1 2.048(12) . ?
C21 C22 1.41(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.39(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.39(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.42(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.46(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 Au1 2.112(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 122.1(11) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 118.2(12) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 119.9(13) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.3(12) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 119.4(11) . . ?
N1 C5 C6 115.0(10) . . ?
C4 C5 C6 125.6(10) . . ?
C7 C6 C11 118.6(11) . . ?
C7 C6 C5 123.2(11) . . ?
C11 C6 C5 118.2(10) . . ?
C8 C7 C6 120.4(12) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.0(11) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 118.5(12) . . ?
C8 C9 C12 122.0(12) . . ?
C10 C9 C12 119.5(13) . . ?
C11 C10 C9 121.9(12) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C6 119.5(10) . . ?
C10 C11 Au1 128.5(9) . . ?
C6 C11 Au1 112.0(8) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 117.8(10) . . ?
C18 C13 Au1 121.2(9) . . ?
C14 C13 Au1 120.7(9) . . ?
C15 C14 C13 122.1(12) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 119.3(13) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 119.6(12) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 122.1(13) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C13 C18 C17 119.3(12) . . ?
C13 C18 C19 121.2(11) . . ?
C17 C18 C19 119.5(12) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 120.6(12) . . ?
C21 C20 Au1 120.1(10) . . ?
C25 C20 Au1 119.2(11) . . ?
C20 C21 C22 121.1(14) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 120.3(15) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 117.8(14) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
C23 C24 C25 122.7(14) . . ?
C23 C24 H24 118.7 . . ?
C25 C24 H24 118.7 . . ?
C20 C25 C24 117.3(13) . . ?
C20 C25 C26 123.7(13) . . ?
C24 C25 C26 118.9(13) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 N1 C5 120.1(10) . . ?
C1 N1 Au1 125.3(8) . . ?
C5 N1 Au1 114.5(8) . . ?
C20 Au1 C11 93.3(5) . . ?
C20 Au1 C13 91.3(5) . . ?
C11 Au1 C13 175.2(5) . . ?
C20 Au1 N1 173.3(4) . . ?
C11 Au1 N1 80.1(4) . . ?
C13 Au1 N1 95.2(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
N1 C1 C2 C3 3(2) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 C5 -1(2) . . . . ?
C3 C4 C5 N1 1(2) . . . . ?
C3 C4 C5 C6 -177.5(13) . . . . ?
N1 C5 C6 C7 -179.6(12) . . . . ?
C4 C5 C6 C7 -1(2) . . . . ?
N1 C5 C6 C11 2.0(17) . . . . ?
C4 C5 C6 C11 -179.7(13) . . . . ?
C11 C6 C7 C8 0(2) . . . . ?
C5 C6 C7 C8 -178.2(13) . . . . ?
C6 C7 C8 C9 1(2) . . . . ?
C7 C8 C9 C10 -1(2) . . . . ?
C7 C8 C9 C12 -179.5(14) . . . . ?
C8 C9 C10 C11 -1(2) . . . . ?
C12 C9 C10 C11 177.7(13) . . . . ?
C9 C10 C11 C6 2.3(19) . . . . ?
C9 C10 C11 Au1 -177.4(10) . . . . ?
C7 C6 C11 C10 -2.0(19) . . . . ?
C5 C6 C11 C10 176.6(12) . . . . ?
C7 C6 C11 Au1 177.8(10) . . . . ?
C5 C6 C11 Au1 -3.6(15) . . . . ?
C18 C13 C14 C15 0(2) . . . . ?
Au1 C13 C14 C15 -173.7(12) . . . . ?
C13 C14 C15 C16 1(2) . . . . ?
C14 C15 C16 C17 -1(2) . . . . ?
C15 C16 C17 C18 1(2) . . . . ?
C14 C13 C18 C17 0(2) . . . . ?
Au1 C13 C18 C17 173.5(10) . . . . ?
C14 C13 C18 C19 -177.0(14) . . . . ?
Au1 C13 C18 C19 -3.2(19) . . . . ?
C16 C17 C18 C13 0(2) . . . . ?
C16 C17 C18 C19 176.5(14) . . . . ?
C25 C20 C21 C22 0(2) . . . . ?
Au1 C20 C21 C22 176.2(10) . . . . ?
C20 C21 C22 C23 -2(2) . . . . ?
C21 C22 C23 C24 4(2) . . . . ?
C22 C23 C24 C25 -5(2) . . . . ?
C21 C20 C25 C24 -1.2(18) . . . . ?
Au1 C20 C25 C24 -177.0(9) . . . . ?
C21 C20 C25 C26 -180.0(13) . . . . ?
Au1 C20 C25 C26 4.2(17) . . . . ?
C23 C24 C25 C20 3.5(19) . . . . ?
C23 C24 C25 C26 -177.6(13) . . . . ?
C2 C1 N1 C5 -4(2) . . . . ?
C2 C1 N1 Au1 175.8(10) . . . . ?
C4 C5 N1 C1 1.8(19) . . . . ?
C6 C5 N1 C1 -179.8(12) . . . . ?
C4 C5 N1 Au1 -177.7(10) . . . . ?
C6 C5 N1 Au1 0.7(14) . . . . ?

_refine_diff_density_max         4.580
_refine_diff_density_min         -4.126
_refine_diff_density_rms         0.344

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1009039'
#######################################################################
#
#                 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_Quest14mz050_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H32 Au N O2'
_chemical_formula_weight         635.53

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.4071(9)
_cell_length_b                   15.6565(7)
_cell_length_c                   19.6251(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.0780(10)
_cell_angle_gamma                90
_cell_volume                     5525.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9259
_cell_measurement_theta_min      2.5167
_cell_measurement_theta_max      30.5393

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             2512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.349
_shelx_estimated_absorpt_T_min   0.360
_shelx_estimated_absorpt_T_max   0.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4145
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Apex2 v2014.1-1 (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26992
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.265
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8316
_reflns_number_gt                7095
_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       'Apex2 v2014.1-1 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev645 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0196P)²+51.1794P] 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         8316
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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_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 0.1194(3) 1.0354(3) 0.1886(3) 0.0415(11) Uani 1 1 d . . . . .
H1 H 0.1158 1.0771 0.1523 0.050 Uiso 1 1 calc R U . . .
C2 C 0.1155(4) 1.0615(4) 0.2539(3) 0.0553(15) Uani 1 1 d . . . . .
H2 H 0.1092 1.1201 0.2626 0.066 Uiso 1 1 calc R U . . .
C3 C 0.1208(4) 1.0006(4) 0.3066(3) 0.0541(15) Uani 1 1 d . . . . .
H3 H 0.1178 1.0170 0.3520 0.065 Uiso 1 1 calc R U . . .
C4 C 0.1305(3) 0.9156(3) 0.2929(3) 0.0430(11) Uani 1 1 d . . . . .
H4 H 0.1352 0.8734 0.3292 0.052 Uiso 1 1 calc R U . . .
C5 C 0.1334(3) 0.8925(3) 0.2253(2) 0.0313(9) Uani 1 1 d . . . . .
C6 C 0.1399(3) 0.8042(3) 0.2025(2) 0.0325(9) Uani 1 1 d . . . . .
C7 C 0.1528(3) 0.7345(3) 0.2496(3) 0.0445(12) Uani 1 1 d . . . . .
H7 H 0.1574 0.7425 0.2991 0.053 Uiso 1 1 calc R U . . .
C8 C 0.1590(4) 0.6536(3) 0.2242(3) 0.0529(14) Uani 1 1 d . . . . .
H8 H 0.1683 0.6065 0.2569 0.063 Uiso 1 1 calc R U . . .
C9 C 0.1519(3) 0.6398(3) 0.1519(3) 0.0449(12) Uani 1 1 d . . . . .
C10 C 0.1388(3) 0.7100(3) 0.1053(3) 0.0324(9) Uani 1 1 d . . . . .
H10 H 0.1334 0.7012 0.0556 0.039 Uiso 1 1 calc R U . . .
C11 C 0.1335(2) 0.7929(3) 0.1288(2) 0.0267(8) Uani 1 1 d . . . . .
C12 C 0.1589(4) 0.5513(3) 0.1245(4) 0.0641(18) Uani 1 1 d . . . . .
H12A H 0.1675 0.5557 0.0785 0.096 Uiso 1 1 calc R U . . .
H12B H 0.1129 0.5193 0.1157 0.096 Uiso 1 1 calc R U . . .
H12C H 0.2008 0.5215 0.1615 0.096 Uiso 1 1 calc R U . . .
C13 C 0.1251(2) 1.0233(3) 0.0230(2) 0.0273(8) Uani 1 1 d . . . . .
C14 C 0.0634(2) 1.0522(3) -0.0357(2) 0.0288(8) Uani 1 1 d . . . . .
H14 H 0.0211 1.0161 -0.0550 0.035 Uiso 1 1 calc R U . . .
C15 C 0.0614(2) 1.1323(3) -0.0674(3) 0.0325(9) Uani 1 1 d . . . . .
H15 H 0.0183 1.1502 -0.1075 0.039 Uiso 1 1 calc R U . . .
C16 C 0.1228(3) 1.1856(3) -0.0398(2) 0.0321(9) Uani 1 1 d . . . . .
C17 C 0.1853(3) 1.1590(3) 0.0176(3) 0.0435(12) Uani 1 1 d . . . . .
H17 H 0.2277 1.1950 0.0360 0.052 Uiso 1 1 calc R U . . .
C18 C 0.1859(3) 1.0787(3) 0.0488(3) 0.0422(12) Uani 1 1 d . . . . .
H18 H 0.2292 1.0611 0.0888 0.051 Uiso 1 1 calc R U . . .
C19 C 0.0633(3) 1.3218(3) -0.0824(3) 0.0380(10) Uani 1 1 d . . . . .
H19 H 0.0158 1.2916 -0.1110 0.046 Uiso 1 1 calc R U . . .
C20 C 0.0728(5) 1.3958(4) -0.1277(4) 0.070(2) Uani 1 1 d . . . . .
H20A H 0.0712 1.3746 -0.1753 0.105 Uiso 1 1 calc R U . . .
H20B H 0.1208 1.4236 -0.1015 0.105 Uiso 1 1 calc R U . . .
H20C H 0.0326 1.4372 -0.1356 0.105 Uiso 1 1 calc R U . . .
C21 C 0.0613(4) 1.3499(4) -0.0102(4) 0.0635(17) Uani 1 1 d . . . . .
H21A H 0.0235 1.3944 -0.0186 0.095 Uiso 1 1 calc R U . . .
H21B H 0.1101 1.3725 0.0209 0.095 Uiso 1 1 calc R U . . .
H21C H 0.0490 1.3010 0.0143 0.095 Uiso 1 1 calc R U . . .
C22 C 0.1213(2) 0.8501(2) -0.0205(2) 0.0237(7) Uani 1 1 d . . . . .
C23 C 0.1844(2) 0.8322(3) -0.0347(2) 0.0369(10) Uani 1 1 d . . . . .
H23 H 0.2315 0.8502 -0.0007 0.044 Uiso 1 1 calc R U . . .
C24 C 0.1804(2) 0.7882(4) -0.0978(2) 0.0409(11) Uani 1 1 d . . . . .
H24 H 0.2246 0.7759 -0.1060 0.049 Uiso 1 1 calc R U . . .
C25 C 0.1126(2) 0.7625(3) -0.1482(2) 0.0291(8) Uani 1 1 d . . . . .
C26 C 0.0489(2) 0.7805(3) -0.1356(2) 0.0312(8) Uani 1 1 d . . . . .
H26 H 0.0019 0.7635 -0.1705 0.037 Uiso 1 1 calc R U . . .
C27 C 0.0528(2) 0.8232(3) -0.0722(2) 0.0326(9) Uani 1 1 d . . . . .
H27 H 0.0085 0.8342 -0.0638 0.039 Uiso 1 1 calc R U . . .
C28 C 0.1637(3) 0.6820(3) -0.2245(2) 0.0359(10) Uani 1 1 d . . . . .
H28 H 0.2103 0.7159 -0.2005 0.043 Uiso 1 1 calc R U . . .
C29 C 0.1453(3) 0.6775(4) -0.3066(3) 0.0495(13) Uani 1 1 d . . . . .
H29A H 0.0995 0.6445 -0.3300 0.074 Uiso 1 1 calc R U . . .
H29B H 0.1861 0.6496 -0.3158 0.074 Uiso 1 1 calc R U . . .
H29C H 0.1383 0.7354 -0.3270 0.074 Uiso 1 1 calc R U . . .
C30 C 0.1729(3) 0.5947(3) -0.1899(3) 0.0468(13) Uani 1 1 d . . . . .
H30A H 0.1263 0.5628 -0.2115 0.070 Uiso 1 1 calc R U . . .
H30B H 0.1859 0.6006 -0.1368 0.070 Uiso 1 1 calc R U . . .
H30C H 0.2127 0.5640 -0.1990 0.070 Uiso 1 1 calc R U . . .
N1 N 0.1282(2) 0.9537(2) 0.17429(19) 0.0296(7) Uani 1 1 d . . . . .
O1 O 0.1253(2) 1.2640(2) -0.0720(2) 0.0407(8) Uani 1 1 d . . . . .
O2 O 0.10279(18) 0.7249(2) -0.21510(16) 0.0352(7) Uani 1 1 d . . . . .
Au1 Au 0.12651(2) 0.90614(2) 0.07279(2) 0.02369(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
C1 N1 1.335(6) . ?
C1 C2 1.374(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(6) . ?
C4 H4 0.9500 . ?
C5 N1 1.361(5) . ?
C5 C6 1.473(6) . ?
C6 C7 1.391(6) . ?
C6 C11 1.415(6) . ?
C7 C8 1.383(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(6) . ?
C9 C12 1.511(7) . ?
C10 C11 1.393(6) . ?
C10 H10 0.9500 . ?
C11 Au1 2.064(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.390(6) . ?
C13 C18 1.398(6) . ?
C13 Au1 2.073(4) . ?
C14 C15 1.393(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(7) . ?
C16 O1 1.390(5) . ?
C17 C18 1.396(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 O1 1.457(6) . ?
C19 C21 1.498(7) . ?
C19 C20 1.514(7) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.382(6) . ?
C22 C27 1.401(6) . ?
C22 Au1 1.999(4) . ?
C23 C24 1.393(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.378(6) . ?
C25 O2 1.385(5) . ?
C26 C27 1.389(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 O2 1.430(5) . ?
C28 C30 1.506(7) . ?
C28 C29 1.516(7) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N1 Au1 2.115(3) . ?

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 122.5(5) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.6(5) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 119.7(5) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.3(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 119.9(4) . . ?
N1 C5 C6 115.3(4) . . ?
C4 C5 C6 124.8(4) . . ?
C7 C6 C11 120.4(4) . . ?
C7 C6 C5 123.3(4) . . ?
C11 C6 C5 116.4(4) . . ?
C8 C7 C6 119.8(5) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 121.5(5) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 118.1(5) . . ?
C8 C9 C12 121.2(5) . . ?
C10 C9 C12 120.6(5) . . ?
C9 C10 C11 122.4(4) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C6 117.8(4) . . ?
C10 C11 Au1 128.4(3) . . ?
C6 C11 Au1 113.5(3) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 116.4(4) . . ?
C14 C13 Au1 122.3(3) . . ?
C18 C13 Au1 121.3(3) . . ?
C13 C14 C15 122.4(4) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C16 C15 C14 119.4(4) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 O1 118.0(4) . . ?
C15 C16 O1 121.7(4) . . ?
C16 C17 C18 119.5(4) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C13 122.3(4) . . ?
C17 C18 H18 118.9 . . ?
C13 C18 H18 118.9 . . ?
O1 C19 C21 111.3(5) . . ?
O1 C19 C20 106.3(4) . . ?
C21 C19 C20 112.5(5) . . ?
O1 C19 H19 108.9 . . ?
C21 C19 H19 108.9 . . ?
C20 C19 H19 108.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 117.7(4) . . ?
C23 C22 Au1 122.0(3) . . ?
C27 C22 Au1 120.1(3) . . ?
C22 C23 C24 121.5(4) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C25 C24 C23 120.1(4) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.4(4) . . ?
C24 C25 O2 124.0(4) . . ?
C26 C25 O2 116.4(4) . . ?
C25 C26 C27 120.6(4) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C22 120.7(4) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
O2 C28 C30 109.5(4) . . ?
O2 C28 C29 106.4(4) . . ?
C30 C28 C29 112.1(4) . . ?
O2 C28 H28 109.6 . . ?
C30 C28 H28 109.6 . . ?
C29 C28 H28 109.6 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C1 N1 C5 120.0(4) . . ?
C1 N1 Au1 125.3(3) . . ?
C5 N1 Au1 114.6(3) . . ?
C16 O1 C19 116.3(4) . . ?
C25 O2 C28 119.7(3) . . ?
C22 Au1 C11 94.69(16) . . ?
C22 Au1 C13 88.24(16) . . ?
C11 Au1 C13 176.06(16) . . ?
C22 Au1 N1 174.24(15) . . ?
C11 Au1 N1 79.97(15) . . ?
C13 Au1 N1 97.19(15) . . ?

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
N1 C1 C2 C3 0.0(10) . . . . ?
C1 C2 C3 C4 0.6(10) . . . . ?
C2 C3 C4 C5 -1.3(9) . . . . ?
C3 C4 C5 N1 1.4(8) . . . . ?
C3 C4 C5 C6 -176.9(5) . . . . ?
N1 C5 C6 C7 173.7(5) . . . . ?
C4 C5 C6 C7 -7.9(8) . . . . ?
N1 C5 C6 C11 -5.3(6) . . . . ?
C4 C5 C6 C11 173.1(5) . . . . ?
C11 C6 C7 C8 -0.4(8) . . . . ?
C5 C6 C7 C8 -179.3(5) . . . . ?
C6 C7 C8 C9 -0.6(9) . . . . ?
C7 C8 C9 C10 0.4(9) . . . . ?
C7 C8 C9 C12 179.8(6) . . . . ?
C8 C9 C10 C11 0.7(8) . . . . ?
C12 C9 C10 C11 -178.7(5) . . . . ?
C9 C10 C11 C6 -1.6(7) . . . . ?
C9 C10 C11 Au1 172.3(4) . . . . ?
C7 C6 C11 C10 1.5(7) . . . . ?
C5 C6 C11 C10 -179.6(4) . . . . ?
C7 C6 C11 Au1 -173.3(4) . . . . ?
C5 C6 C11 Au1 5.6(5) . . . . ?
C18 C13 C14 C15 -0.5(7) . . . . ?
Au1 C13 C14 C15 177.5(3) . . . . ?
C13 C14 C15 C16 0.0(7) . . . . ?
C14 C15 C16 C17 0.8(7) . . . . ?
C14 C15 C16 O1 176.2(4) . . . . ?
C15 C16 C17 C18 -1.2(8) . . . . ?
O1 C16 C17 C18 -176.8(5) . . . . ?
C16 C17 C18 C13 0.7(9) . . . . ?
C14 C13 C18 C17 0.2(8) . . . . ?
Au1 C13 C18 C17 -177.9(4) . . . . ?
C27 C22 C23 C24 -0.5(7) . . . . ?
Au1 C22 C23 C24 175.8(4) . . . . ?
C22 C23 C24 C25 0.8(8) . . . . ?
C23 C24 C25 C26 -0.1(8) . . . . ?
C23 C24 C25 O2 174.4(4) . . . . ?
C24 C25 C26 C27 -0.8(7) . . . . ?
O2 C25 C26 C27 -175.8(4) . . . . ?
C25 C26 C27 C22 1.2(7) . . . . ?
C23 C22 C27 C26 -0.5(7) . . . . ?
Au1 C22 C27 C26 -176.8(3) . . . . ?
C2 C1 N1 C5 0.2(8) . . . . ?
C2 C1 N1 Au1 175.0(5) . . . . ?
C4 C5 N1 C1 -0.9(7) . . . . ?
C6 C5 N1 C1 177.6(4) . . . . ?
C4 C5 N1 Au1 -176.2(4) . . . . ?
C6 C5 N1 Au1 2.3(5) . . . . ?
C17 C16 O1 C19 -131.3(5) . . . . ?
C15 C16 O1 C19 53.2(6) . . . . ?
C21 C19 O1 C16 65.2(6) . . . . ?
C20 C19 O1 C16 -171.9(5) . . . . ?
C24 C25 O2 C28 23.5(6) . . . . ?
C26 C25 O2 C28 -161.9(4) . . . . ?
C30 C28 O2 C25 78.9(5) . . . . ?
C29 C28 O2 C25 -159.7(4) . . . . ?

_refine_diff_density_max         3.567
_refine_diff_density_min         -1.025
_refine_diff_density_rms         0.151

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1009040'
#######################################################################
#
#                 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_13mz261_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Au Cl F N'
_chemical_formula_weight         495.72

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4066(10)
_cell_length_b                   13.2270(14)
_cell_length_c                   13.1786(14)
_cell_angle_alpha                90
_cell_angle_beta                 110.251(2)
_cell_angle_gamma                90
_cell_volume                     1538.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4302
_cell_measurement_theta_min      2.2566
_cell_measurement_theta_max      31.1557

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.140
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    9.742
_shelx_estimated_absorpt_T_min   0.152
_shelx_estimated_absorpt_T_max   0.414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4180
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'Apex2 v2013.4-1 (Bruker, 2013)'

_exptl_special_details           
;
Reflections 0 1 1 and 1 0 0 were affected by the beam stop 
and were omitted from the refinement. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9244
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.775
_diffrn_reflns_theta_max         31.467
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4645
_reflns_number_gt                4016
_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       'Apex2 v2013.4-1 (Bruker, 2013)'
_computing_cell_refinement       'SAINT V8.30C (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev645 (Hübschle et al., 2011)
;
_computing_molecular_graphics    'Shelxtl (Bruker, 2003)'
_computing_publication_material  'Shelxtl (Bruker, 2003)'

_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)+(0.0422P)²] 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         4645
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0750
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
C1 C 0.8198(5) -0.0876(3) 0.7094(3) 0.0147(8) Uani 1 1 d . . . . .
H1 H 0.7240 -0.1022 0.7151 0.018 Uiso 1 1 calc R U . . .
C2 C 0.9396(5) -0.1513(3) 0.7582(3) 0.0176(8) Uani 1 1 d . . . . .
H2 H 0.9257 -0.2100 0.7952 0.021 Uiso 1 1 calc R U . . .
C3 C 1.0805(5) -0.1289(3) 0.7529(4) 0.0192(9) Uani 1 1 d . . . . .
H3 H 1.1656 -0.1704 0.7886 0.023 Uiso 1 1 calc R U . . .
C4 C 1.0955(4) -0.0448(3) 0.6944(3) 0.0135(7) Uani 1 1 d . . . . .
H4 H 1.1907 -0.0294 0.6879 0.016 Uiso 1 1 calc R U . . .
C5 C 0.9708(4) 0.0169(3) 0.6453(3) 0.0101(7) Uani 1 1 d . . . . .
C6 C 0.9709(4) 0.1095(3) 0.5836(3) 0.0114(7) Uani 1 1 d . . . . .
C7 C 1.0974(4) 0.1409(3) 0.5591(3) 0.0124(7) Uani 1 1 d . . . . .
H7 H 1.1880 0.1022 0.5840 0.015 Uiso 1 1 calc R U . . .
C8 C 1.0923(5) 0.2274(3) 0.4994(3) 0.0148(8) Uani 1 1 d . . . . .
H8 H 1.1790 0.2478 0.4834 0.018 Uiso 1 1 calc R U . . .
C9 C 0.9596(5) 0.2850(3) 0.4624(3) 0.0140(7) Uani 1 1 d . . . . .
C10 C 0.8351(5) 0.2555(3) 0.4885(3) 0.0151(8) Uani 1 1 d . . . . .
H10 H 0.7461 0.2958 0.4655 0.018 Uiso 1 1 calc R U . . .
C11 C 0.8380(4) 0.1679(3) 0.5479(3) 0.0110(7) Uani 1 1 d . . . . .
C12 C 0.9514(6) 0.3788(3) 0.3956(4) 0.0236(10) Uani 1 1 d . . . . .
H12A H 0.9767 0.3616 0.3315 0.035 Uiso 1 1 calc R U . . .
H12B H 1.0235 0.4291 0.4389 0.035 Uiso 1 1 calc R U . . .
H12C H 0.8486 0.4067 0.3729 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5362(4) 0.2317(3) 0.5422(3) 0.0123(7) Uani 1 1 d . . . . .
C14 C 0.4727(4) 0.2585(3) 0.4335(3) 0.0155(8) Uani 1 1 d . . . . .
H14 H 0.4866 0.2157 0.3797 0.019 Uiso 1 1 calc R U . . .
C15 C 0.3887(5) 0.3476(4) 0.4027(4) 0.0210(9) Uani 1 1 d . . . . .
H15 H 0.3449 0.3658 0.3286 0.025 Uiso 1 1 calc R U . . .
C16 C 0.3713(5) 0.4079(3) 0.4818(4) 0.0200(9) Uani 1 1 d . . . . .
C17 C 0.4311(5) 0.3847(3) 0.5895(4) 0.0192(9) Uani 1 1 d . . . . .
H17 H 0.4172 0.4285 0.6424 0.023 Uiso 1 1 calc R U . . .
C18 C 0.5124(5) 0.2958(3) 0.6195(3) 0.0166(8) Uani 1 1 d . . . . .
H18 H 0.5528 0.2779 0.6938 0.020 Uiso 1 1 calc R U . . .
N1 N 0.8341(4) -0.0055(2) 0.6537(3) 0.0116(6) Uani 1 1 d . . . . .
F1 F 0.2910(3) 0.4954(2) 0.4522(3) 0.0313(7) Uani 1 1 d . . . . .
Cl1 Cl 0.48513(11) 0.02985(8) 0.65039(8) 0.0192(2) Uani 1 1 d . . . . .
Au1 Au 0.66945(2) 0.10890(2) 0.59185(2) 0.01042(6) 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 N1 1.343(5) . ?
C1 C2 1.375(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.361(5) . ?
C5 C6 1.470(5) . ?
C6 C7 1.399(5) . ?
C6 C11 1.405(5) . ?
C7 C8 1.380(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(5) . ?
C9 C12 1.508(6) . ?
C10 C11 1.393(5) . ?
C10 H10 0.9500 . ?
C11 Au1 2.023(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.394(5) . ?
C13 C18 1.402(5) . ?
C13 Au1 2.018(4) . ?
C14 C15 1.399(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.367(7) . ?
C15 H15 0.9500 . ?
C16 F1 1.364(5) . ?
C16 C17 1.368(7) . ?
C17 C18 1.383(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 Au1 2.116(3) . ?
Cl1 Au1 2.3707(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 122.0(4) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 118.9(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 120.2(3) . . ?
N1 C5 C6 114.1(3) . . ?
C4 C5 C6 125.7(3) . . ?
C7 C6 C11 119.3(3) . . ?
C7 C6 C5 122.6(4) . . ?
C11 C6 C5 118.2(3) . . ?
C8 C7 C6 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 C12 120.0(4) . . ?
C8 C9 C12 120.7(4) . . ?
C9 C10 C11 121.3(4) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C6 119.2(3) . . ?
C10 C11 Au1 128.1(3) . . ?
C6 C11 Au1 112.8(3) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 118.3(4) . . ?
C14 C13 Au1 122.3(3) . . ?
C18 C13 Au1 119.3(3) . . ?
C13 C14 C15 120.7(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 118.3(4) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
F1 C16 C15 118.5(4) . . ?
F1 C16 C17 118.4(4) . . ?
C15 C16 C17 123.1(4) . . ?
C16 C17 C18 118.4(4) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C13 121.2(4) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C1 N1 C5 119.8(3) . . ?
C1 N1 Au1 126.2(3) . . ?
C5 N1 Au1 113.5(2) . . ?
C13 Au1 C11 93.26(15) . . ?
C13 Au1 N1 171.99(14) . . ?
C11 Au1 N1 81.05(14) . . ?
C13 Au1 Cl1 91.07(10) . . ?
C11 Au1 Cl1 175.59(11) . . ?
N1 Au1 Cl1 94.56(9) . . ?

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
N1 C1 C2 C3 1.9(6) . . . . ?
C1 C2 C3 C4 -2.6(7) . . . . ?
C2 C3 C4 C5 2.0(6) . . . . ?
C3 C4 C5 N1 -0.6(6) . . . . ?
C3 C4 C5 C6 178.3(4) . . . . ?
N1 C5 C6 C7 -175.1(3) . . . . ?
C4 C5 C6 C7 6.1(6) . . . . ?
N1 C5 C6 C11 4.7(5) . . . . ?
C4 C5 C6 C11 -174.2(4) . . . . ?
C11 C6 C7 C8 -0.9(6) . . . . ?
C5 C6 C7 C8 178.9(3) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C7 C8 C9 C10 1.5(6) . . . . ?
C7 C8 C9 C12 -179.0(4) . . . . ?
C8 C9 C10 C11 -2.1(6) . . . . ?
C12 C9 C10 C11 178.4(4) . . . . ?
C9 C10 C11 C6 1.2(6) . . . . ?
C9 C10 C11 Au1 -178.4(3) . . . . ?
C7 C6 C11 C10 0.3(5) . . . . ?
C5 C6 C11 C10 -179.5(3) . . . . ?
C7 C6 C11 Au1 179.9(3) . . . . ?
C5 C6 C11 Au1 0.2(4) . . . . ?
C18 C13 C14 C15 0.7(6) . . . . ?
Au1 C13 C14 C15 -176.0(3) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C14 C15 C16 F1 179.2(4) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
F1 C16 C17 C18 180.0(4) . . . . ?
C15 C16 C17 C18 -0.3(7) . . . . ?
C16 C17 C18 C13 1.3(6) . . . . ?
C14 C13 C18 C17 -1.5(6) . . . . ?
Au1 C13 C18 C17 175.2(3) . . . . ?
C2 C1 N1 C5 -0.4(6) . . . . ?
C2 C1 N1 Au1 -171.6(3) . . . . ?
C4 C5 N1 C1 -0.2(5) . . . . ?
C6 C5 N1 C1 -179.2(3) . . . . ?
C4 C5 N1 Au1 172.0(3) . . . . ?
C6 C5 N1 Au1 -7.0(4) . . . . ?

_refine_diff_density_max         2.970
_refine_diff_density_min         -1.606
_refine_diff_density_rms         0.214

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1009041'
#######################################################################
#
#                 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_13mz264_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 Au Cl N'
_chemical_formula_weight         527.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.340(2)
_cell_length_b                   18.881(4)
_cell_length_c                   9.579(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.408(3)
_cell_angle_gamma                90
_cell_volume                     1752.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6777
_cell_measurement_theta_min      2.3623
_cell_measurement_theta_max      31.2424

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.000
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    8.549
_shelx_estimated_absorpt_T_min   0.144
_shelx_estimated_absorpt_T_max   0.628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3831
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'Apex2 v2013.4-1 (Bruker, 2013)'

_exptl_special_details           
;
Reflection 0 2 0 was affected by the beam stop and was omitted 
from the refinement.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19661
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4345
_reflns_number_gt                3597
_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       'Apex2 v2013.4-1 (Bruker, 2013)'
_computing_cell_refinement       'SAINT V8.30C (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev645 (Hübschle et al., 2011)
;
_computing_molecular_graphics    'Shelxtl (Bruker, 2003)'
_computing_publication_material  'Shelxtl (Bruker, 2003)'

_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)+(0.0480P)²] 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         4345
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_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 0.6427(5) 0.5309(3) 0.6878(5) 0.0227(10) Uani 1 1 d . . . . .
H1 H 0.6613 0.5792 0.6745 0.027 Uiso 1 1 calc R U . . .
C2 C 0.7220(6) 0.4794(3) 0.6556(6) 0.0289(11) Uani 1 1 d . . . . .
H2 H 0.7947 0.4919 0.6211 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6940(6) 0.4091(2) 0.6743(6) 0.0277(12) Uani 1 1 d . . . . .
H3 H 0.7473 0.3728 0.6519 0.033 Uiso 1 1 calc R U . . .
C4 C 0.5889(5) 0.3917(3) 0.7254(5) 0.0223(10) Uani 1 1 d . . . . .
H4 H 0.5690 0.3435 0.7380 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5122(5) 0.4458(2) 0.7584(5) 0.0177(9) Uani 1 1 d . . . . .
C6 C 0.4002(5) 0.4367(2) 0.8160(5) 0.0174(9) Uani 1 1 d . . . . .
C7 C 0.3605(5) 0.3705(2) 0.8538(5) 0.0222(10) Uani 1 1 d . . . . .
H7 H 0.4069 0.3290 0.8406 0.027 Uiso 1 1 calc R U . . .
C8 C 0.2565(5) 0.3649(2) 0.9091(5) 0.0231(10) Uani 1 1 d . . . . .
H8 H 0.2346 0.3196 0.9379 0.028 Uiso 1 1 calc R U . . .
C9 C 0.1812(5) 0.4234(2) 0.9248(5) 0.0209(10) Uani 1 1 d . . . . .
C10 C 0.2197(5) 0.4901(2) 0.8877(5) 0.0192(9) Uani 1 1 d . . . . .
H10 H 0.1712 0.5311 0.8998 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3269(5) 0.4974(2) 0.8339(5) 0.0166(9) Uani 1 1 d . . . . .
C12 C 0.0616(7) 0.4147(3) 0.9778(7) 0.0320(13) Uani 1 1 d . . . . .
H12A H -0.0129 0.4469 0.9223 0.048 Uiso 1 1 calc R U . . .
H12B H 0.0913 0.4258 1.0843 0.048 Uiso 1 1 calc R U . . .
H12C H 0.0284 0.3657 0.9615 0.048 Uiso 1 1 calc R U . . .
C13 C 0.2520(5) 0.6486(2) 0.8061(5) 0.0158(9) Uani 1 1 d . . . . .
C14 C 0.2902(5) 0.6964(2) 0.9212(5) 0.0215(10) Uani 1 1 d . . . . .
H14 H 0.3850 0.7013 0.9801 0.026 Uiso 1 1 calc R U . . .
C15 C 0.1913(5) 0.7382(2) 0.9536(5) 0.0219(10) Uani 1 1 d . . . . .
H15 H 0.2200 0.7696 1.0363 0.026 Uiso 1 1 calc R U . . .
C16 C 0.0565(5) 0.7343(2) 0.8685(5) 0.0210(10) Uani 1 1 d . . . . .
H16 H -0.0089 0.7630 0.8913 0.025 Uiso 1 1 calc R U . . .
C17 C 0.0119(5) 0.6872(2) 0.7447(5) 0.0173(9) Uani 1 1 d . . . . .
C18 C -0.1291(5) 0.6820(2) 0.6535(5) 0.0219(10) Uani 1 1 d . . . . .
H18 H -0.1958 0.7087 0.6784 0.026 Uiso 1 1 calc R U . . .
C19 C -0.1706(5) 0.6396(3) 0.5315(6) 0.0247(10) Uani 1 1 d . . . . .
H19 H -0.2652 0.6377 0.4702 0.030 Uiso 1 1 calc R U . . .
C20 C -0.0721(6) 0.5982(2) 0.4957(6) 0.0221(10) Uani 1 1 d . . . . .
H20 H -0.1007 0.5690 0.4094 0.027 Uiso 1 1 calc R U . . .
C21 C 0.0629(5) 0.5999(2) 0.5844(5) 0.0193(10) Uani 1 1 d . . . . .
H21 H 0.1271 0.5707 0.5607 0.023 Uiso 1 1 calc R U . . .
C22 C 0.1103(4) 0.6443(2) 0.7115(5) 0.0161(9) Uani 1 1 d . . . . .
N24 N 0.5400(4) 0.51504(19) 0.7374(4) 0.0183(8) Uani 1 1 d . . . . .
Cl4 Cl 0.50332(12) 0.68746(5) 0.70775(14) 0.0227(2) Uani 1 1 d . . . . .
Au1 Au 0.39920(2) 0.58747(2) 0.77315(2) 0.01432(7) 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 N24 1.340(6) . ?
C1 C2 1.374(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(7) . ?
C4 H4 0.9500 . ?
C5 N24 1.368(6) . ?
C5 C6 1.456(7) . ?
C6 C7 1.402(6) . ?
C6 C11 1.418(6) . ?
C7 C8 1.358(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(6) . ?
C9 C12 1.500(8) . ?
C10 C11 1.383(7) . ?
C10 H10 0.9500 . ?
C11 Au1 2.023(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.371(6) . ?
C13 C22 1.431(6) . ?
C13 Au1 2.021(4) . ?
C14 C15 1.410(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.349(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.425(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.417(7) . ?
C17 C22 1.420(6) . ?
C18 C19 1.357(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.417(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.359(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.417(6) . ?
C21 H21 0.9500 . ?
N24 Au1 2.110(4) . ?
Cl4 Au1 2.3634(11) . ?

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
N24 C1 C2 122.1(5) . . ?
N24 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 118.8(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N24 C5 C4 120.1(5) . . ?
N24 C5 C6 113.8(4) . . ?
C4 C5 C6 126.1(4) . . ?
C7 C6 C11 118.2(4) . . ?
C7 C6 C5 123.1(4) . . ?
C11 C6 C5 118.7(4) . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 122.0(4) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C10 117.8(5) . . ?
C8 C9 C12 120.6(4) . . ?
C10 C9 C12 121.6(4) . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C6 119.8(4) . . ?
C10 C11 Au1 128.0(3) . . ?
C6 C11 Au1 112.2(3) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C22 119.4(4) . . ?
C14 C13 Au1 118.7(3) . . ?
C22 C13 Au1 121.9(3) . . ?
C13 C14 C15 121.2(5) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C22 119.1(4) . . ?
C18 C17 C16 121.4(4) . . ?
C22 C17 C16 119.6(4) . . ?
C19 C18 C17 121.3(5) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 119.7(5) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 120.3(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 121.6(5) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C21 C22 C17 118.0(4) . . ?
C21 C22 C13 123.3(4) . . ?
C17 C22 C13 118.7(4) . . ?
C1 N24 C5 119.9(4) . . ?
C1 N24 Au1 126.1(3) . . ?
C5 N24 Au1 113.8(3) . . ?
C13 Au1 C11 93.53(17) . . ?
C13 Au1 N24 174.37(16) . . ?
C11 Au1 N24 81.19(17) . . ?
C13 Au1 Cl4 91.28(12) . . ?
C11 Au1 Cl4 174.78(14) . . ?
N24 Au1 Cl4 94.07(11) . . ?

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
N24 C1 C2 C3 0.4(8) . . . . ?
C1 C2 C3 C4 -0.5(8) . . . . ?
C2 C3 C4 C5 -0.3(8) . . . . ?
C3 C4 C5 N24 1.2(7) . . . . ?
C3 C4 C5 C6 -178.7(5) . . . . ?
N24 C5 C6 C7 -176.1(4) . . . . ?
C4 C5 C6 C7 3.8(7) . . . . ?
N24 C5 C6 C11 4.3(6) . . . . ?
C4 C5 C6 C11 -175.8(4) . . . . ?
C11 C6 C7 C8 -1.4(7) . . . . ?
C5 C6 C7 C8 179.1(4) . . . . ?
C6 C7 C8 C9 2.8(7) . . . . ?
C7 C8 C9 C10 -2.8(7) . . . . ?
C7 C8 C9 C12 176.4(5) . . . . ?
C8 C9 C10 C11 1.5(7) . . . . ?
C12 C9 C10 C11 -177.7(5) . . . . ?
C9 C10 C11 C6 -0.3(7) . . . . ?
C9 C10 C11 Au1 179.8(4) . . . . ?
C7 C6 C11 C10 0.1(6) . . . . ?
C5 C6 C11 C10 179.7(4) . . . . ?
C7 C6 C11 Au1 -179.9(3) . . . . ?
C5 C6 C11 Au1 -0.3(5) . . . . ?
C22 C13 C14 C15 3.8(7) . . . . ?
Au1 C13 C14 C15 -177.2(3) . . . . ?
C13 C14 C15 C16 -2.4(7) . . . . ?
C14 C15 C16 C17 0.4(7) . . . . ?
C15 C16 C17 C18 180.0(4) . . . . ?
C15 C16 C17 C22 0.1(7) . . . . ?
C22 C17 C18 C19 -3.3(7) . . . . ?
C16 C17 C18 C19 176.8(4) . . . . ?
C17 C18 C19 C20 1.6(7) . . . . ?
C18 C19 C20 C21 1.0(7) . . . . ?
C19 C20 C21 C22 -2.0(7) . . . . ?
C20 C21 C22 C17 0.3(6) . . . . ?
C20 C21 C22 C13 -178.8(4) . . . . ?
C18 C17 C22 C21 2.3(6) . . . . ?
C16 C17 C22 C21 -177.8(4) . . . . ?
C18 C17 C22 C13 -178.6(4) . . . . ?
C16 C17 C22 C13 1.3(6) . . . . ?
C14 C13 C22 C21 175.8(4) . . . . ?
Au1 C13 C22 C21 -3.1(6) . . . . ?
C14 C13 C22 C17 -3.3(6) . . . . ?
Au1 C13 C22 C17 177.8(3) . . . . ?
C2 C1 N24 C5 0.5(7) . . . . ?
C2 C1 N24 Au1 -174.2(4) . . . . ?
C4 C5 N24 C1 -1.3(7) . . . . ?
C6 C5 N24 C1 178.6(4) . . . . ?
C4 C5 N24 Au1 174.1(3) . . . . ?
C6 C5 N24 Au1 -6.0(5) . . . . ?

_refine_diff_density_max         3.606
_refine_diff_density_min         -3.325
_refine_diff_density_rms         0.187

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1009042'
#######################################################################
#
#                 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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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data_Quest14mz061_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Au N O, 0.62(C H2 Cl2)'
_chemical_formula_sum            'C20.62 H17.23 Au Cl1.23 N O'
_chemical_formula_weight         535.71

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   22.3204(12)
_cell_length_b                   11.4097(5)
_cell_length_c                   7.0554(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1796.79(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      2.5543
_cell_measurement_theta_max      35.2497

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.980
_exptl_crystal_F_000             1023.7
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    8.379
_shelx_estimated_absorpt_T_min   0.459
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4897
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_process_details   'Apex2 v2014.1-1 (Bruker, 2014)'

_exptl_special_details           
;
The structure is partially racemically twinned (Flack parameter 0.224(16))
and emulates a higher symmetry centrosymmetric structure with a mirror plane
bisecting the main molecule of the structure. For the C and N atoms directly
located on the pseudo mirror plane, large correlation of position and ADP
results, leading to deformed or non-positive definite ADPs. The thermal
parameters of the affected atoms were restrained to be close to isotropic
(ISOR 0.003 restraint of Shelxl for atoms N1, C1, C2, C6, C11, C10 and C20).

A partially occupied methylene chloride molecule is disordered within channels
parallel to the c-axis. Packing of the solvate molecules in the channels is
incommensurate with the lattice dimensions, and molecules show large ADPs that
stretch along the channel direction if unrestrained. For refinement, the
methylene chloride position was split into two partially occupied molecules
translated from each other by 1.1 and 2.4 Angstroms along the channel. C-Cl
distances were restrained to be similar (SADI), atoms were subjected to a
rigid bond restraint (RIGU), and to be approximately isotropic (ISOR 0.01).
Subject to these conditions occupancy ratios refined to 0.367(16) and 0.250(16),
with a total occupancy for the site of 0.617(16). 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15815
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.553
_diffrn_reflns_theta_max         32.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5456
_reflns_number_gt                4977
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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       'Apex2 v2014.1-1 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2013 (Sheldrick, 2013), 
SHELXLE Rev645 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0186P)²+9.0984P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.224(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5456
_refine_ls_number_parameters     266
_refine_ls_number_restraints     104
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0655
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.047
_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_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 1.0222(2) 1.1633(5) 0.8649(14) 0.0144(13) Uani 1 1 d . U . . .
H1 H 0.9892 1.2154 0.8758 0.017 Uiso 1 1 calc R U . . .
C2 C 1.0798(2) 1.2087(5) 0.8692(14) 0.0176(15) Uani 1 1 d . U . . .
H2 H 1.0862 1.2909 0.8769 0.021 Uiso 1 1 calc R U . . .
C3 C 1.1278(3) 1.1326(6) 0.8621(19) 0.0173(14) Uani 1 1 d . . . . .
H3 H 1.1677 1.1614 0.8699 0.021 Uiso 1 1 calc R U . . .
C4 C 1.1167(2) 1.0122(5) 0.843(3) 0.0188(10) Uani 1 1 d . . . . .
H4 H 1.1493 0.9587 0.8369 0.023 Uiso 1 1 calc R U . . .
C5 C 1.0584(3) 0.9711(5) 0.833(3) 0.0153(15) Uani 1 1 d . . . . .
C6 C 1.0415(3) 0.8477(5) 0.8184(10) 0.0147(14) Uani 1 1 d . U . . .
C7 C 1.0832(3) 0.7585(7) 0.7864(10) 0.0211(14) Uani 1 1 d . . . . .
H7 H 1.1245 0.7770 0.7734 0.025 Uiso 1 1 calc R U . . .
C8 C 1.0643(3) 0.6428(7) 0.7735(11) 0.0236(14) Uani 1 1 d . . . . .
H8 H 1.0929 0.5826 0.7517 0.028 Uiso 1 1 calc R U . . .
C9 C 1.0038(3) 0.6140(6) 0.7922(9) 0.0209(13) Uani 1 1 d . . . . .
C10 C 0.9627(3) 0.7042(5) 0.8222(12) 0.0171(15) Uani 1 1 d . U . . .
H10 H 0.9215 0.6850 0.8363 0.021 Uiso 1 1 calc R U . . .
C11 C 0.9800(2) 0.8217(5) 0.8323(17) 0.0129(12) Uani 1 1 d . U . . .
C12 C 0.9830(4) 0.4882(7) 0.7767(12) 0.0297(17) Uani 1 1 d . . . . .
H12A H 0.9487 0.4838 0.6900 0.045 Uiso 1 1 calc R U . . .
H12B H 0.9710 0.4597 0.9021 0.045 Uiso 1 1 calc R U . . .
H12C H 1.0157 0.4396 0.7278 0.045 Uiso 1 1 calc R U . . .
C13 C 0.8664(2) 1.1077(4) 0.845(2) 0.0148(8) Uani 1 1 d . . . . .
C14 C 0.8741(3) 1.2235(6) 0.7866(10) 0.0210(13) Uani 1 1 d . . . . .
H14 H 0.9104 1.2458 0.7263 0.025 Uiso 1 1 calc R U . . .
C15 C 0.8297(3) 1.3070(6) 0.8149(11) 0.022(2) Uani 1 1 d . . . . .
H15 H 0.8356 1.3846 0.7698 0.026 Uiso 1 1 calc R U . . .
C16 C 0.7768(3) 1.2789(6) 0.9083(11) 0.0249(15) Uani 1 1 d . . . . .
H16 H 0.7480 1.3381 0.9334 0.030 Uiso 1 1 calc R U . . .
C17 C 0.7660(3) 1.1641(7) 0.9650(10) 0.0214(13) Uani 1 1 d . . . . .
H17 H 0.7298 1.1433 1.0272 0.026 Uiso 1 1 calc R U . . .
C18 C 0.8102(3) 1.0801(6) 0.9279(9) 0.0169(12) Uani 1 1 d . . . . .
C19 C 0.8003(3) 0.9541(6) 0.9641(9) 0.0153(12) Uani 1 1 d . . . . .
C20 C 0.8470(2) 0.8775(5) 0.8760(9) 0.0152(14) Uani 1 1 d . U . . .
H20A H 0.8332 0.8507 0.7499 0.018 Uiso 1 1 calc R U . . .
H20B H 0.8535 0.8074 0.9562 0.018 Uiso 1 1 calc R U . . .
C21 C 0.7509(13) 0.634(3) 0.574(8) 0.050(8) Uani 0.250(16) 1 d D U P A 1
H21A H 0.7462 0.7169 0.5351 0.060 Uiso 0.250(16) 1 calc R U P A 1
H21B H 0.7663 0.6341 0.7052 0.060 Uiso 0.250(16) 1 calc R U P A 1
Cl1 Cl 0.6827(7) 0.5736(15) 0.577(3) 0.040(4) Uani 0.250(16) 1 d D U P A 1
Cl2 Cl 0.8037(10) 0.5751(18) 0.436(5) 0.088(9) Uani 0.250(16) 1 d D U P A 1
C21B C 0.7553(8) 0.632(3) 0.728(4) 0.051(6) Uani 0.367(16) 1 d D U P B 2
H21C H 0.7676 0.6119 0.8592 0.061 Uiso 0.367(16) 1 calc R U P B 2
H21D H 0.7504 0.7180 0.7222 0.061 Uiso 0.367(16) 1 calc R U P B 2
Cl1B Cl 0.6891(5) 0.5700(10) 0.686(3) 0.060(5) Uani 0.367(16) 1 d D U P B 2
Cl2B Cl 0.8112(6) 0.5937(11) 0.581(3) 0.062(5) Uani 0.367(16) 1 d D U P B 2
Au2 Au 0.92566(2) 0.96704(2) 0.84765(9) 0.01312(5) Uani 1 1 d . . . . .
N1 N 1.01173(17) 1.0484(4) 0.846(2) 0.0141(7) Uani 1 1 d . U . . .
O1 O 0.7577(2) 0.9141(5) 1.0534(7) 0.0224(11) 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 N1 1.338(7) . ?
C1 C2 1.387(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(7) . ?
C4 H4 0.9500 . ?
C5 N1 1.369(7) . ?
C5 C6 1.462(8) . ?
C6 C7 1.397(9) . ?
C6 C11 1.408(8) . ?
C7 C8 1.389(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(9) . ?
C9 C12 1.513(10) . ?
C10 C11 1.397(8) . ?
C10 H10 0.9500 . ?
C11 Au2 2.058(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.394(10) . ?
C13 C18 1.421(10) . ?
C13 Au2 2.080(5) . ?
C14 C15 1.388(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.399(10) . ?
C17 H17 0.9500 . ?
C18 C19 1.476(9) . ?
C19 O1 1.228(8) . ?
C19 C20 1.497(9) . ?
C20 Au2 2.041(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 Cl2 1.67(2) . ?
C21 Cl1 1.67(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21B Cl1B 1.665(18) . ?
C21B Cl2B 1.68(2) . ?
C21B H21C 0.9900 . ?
C21B H21D 0.9900 . ?
Au2 N1 2.134(4) . ?

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 122.0(5) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 119.0(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.9(5) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 119.6(5) . . ?
N1 C5 C6 115.4(5) . . ?
C4 C5 C6 125.0(5) . . ?
C7 C6 C11 120.5(6) . . ?
C7 C6 C5 122.8(6) . . ?
C11 C6 C5 116.7(5) . . ?
C8 C7 C6 120.0(6) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.8(6) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 118.5(6) . . ?
C8 C9 C12 120.9(7) . . ?
C10 C9 C12 120.5(7) . . ?
C9 C10 C11 122.2(6) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C6 117.9(5) . . ?
C10 C11 Au2 127.8(4) . . ?
C6 C11 Au2 114.1(4) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 116.1(5) . . ?
C14 C13 Au2 131.1(5) . . ?
C18 C13 Au2 112.7(5) . . ?
C15 C14 C13 121.4(7) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 121.1(7) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C17 120.0(6) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 118.0(7) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C17 C18 C13 123.2(6) . . ?
C17 C18 C19 121.9(6) . . ?
C13 C18 C19 114.8(5) . . ?
O1 C19 C18 124.5(6) . . ?
O1 C19 C20 122.3(6) . . ?
C18 C19 C20 113.1(5) . . ?
C19 C20 Au2 110.3(4) . . ?
C19 C20 H20A 109.6 . . ?
Au2 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
Au2 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
Cl2 C21 Cl1 119(2) . . ?
Cl2 C21 H21A 107.5 . . ?
Cl1 C21 H21A 107.5 . . ?
Cl2 C21 H21B 107.5 . . ?
Cl1 C21 H21B 107.5 . . ?
H21A C21 H21B 107.0 . . ?
Cl1B C21B Cl2B 116.1(17) . . ?
Cl1B C21B H21C 108.3 . . ?
Cl2B C21B H21C 108.3 . . ?
Cl1B C21B H21D 108.3 . . ?
Cl2B C21B H21D 108.3 . . ?
H21C C21B H21D 107.4 . . ?
C20 Au2 C11 96.2(2) . . ?
C20 Au2 C13 80.8(2) . . ?
C11 Au2 C13 175.1(4) . . ?
C20 Au2 N1 173.1(4) . . ?
C11 Au2 N1 79.62(18) . . ?
C13 Au2 N1 103.67(16) . . ?
C1 N1 C5 120.3(5) . . ?
C1 N1 Au2 125.7(4) . . ?
C5 N1 Au2 113.9(3) . . ?

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
N1 C1 C2 C3 -2.9(19) . . . . ?
C1 C2 C3 C4 3(2) . . . . ?
C2 C3 C4 C5 -1(3) . . . . ?
C3 C4 C5 N1 -1(3) . . . . ?
C3 C4 C5 C6 -178.4(16) . . . . ?
N1 C5 C6 C7 173.7(11) . . . . ?
C4 C5 C6 C7 -9(2) . . . . ?
N1 C5 C6 C11 -4.6(18) . . . . ?
C4 C5 C6 C11 172.8(16) . . . . ?
C11 C6 C7 C8 -1.8(12) . . . . ?
C5 C6 C7 C8 180.0(11) . . . . ?
C6 C7 C8 C9 0.0(11) . . . . ?
C7 C8 C9 C10 0.6(11) . . . . ?
C7 C8 C9 C12 179.5(7) . . . . ?
C8 C9 C10 C11 0.6(13) . . . . ?
C12 C9 C10 C11 -178.3(9) . . . . ?
C9 C10 C11 C6 -2.4(15) . . . . ?
C9 C10 C11 Au2 173.1(6) . . . . ?
C7 C6 C11 C10 3.0(14) . . . . ?
C5 C6 C11 C10 -178.7(11) . . . . ?
C7 C6 C11 Au2 -173.1(6) . . . . ?
C5 C6 C11 Au2 5.2(13) . . . . ?
C18 C13 C14 C15 2.1(16) . . . . ?
Au2 C13 C14 C15 -173.4(9) . . . . ?
C13 C14 C15 C16 2.2(13) . . . . ?
C14 C15 C16 C17 -3.9(11) . . . . ?
C15 C16 C17 C18 1.0(11) . . . . ?
C16 C17 C18 C13 3.5(13) . . . . ?
C16 C17 C18 C19 -173.4(6) . . . . ?
C14 C13 C18 C17 -5.0(16) . . . . ?
Au2 C13 C18 C17 171.3(6) . . . . ?
C14 C13 C18 C19 172.1(9) . . . . ?
Au2 C13 C18 C19 -11.6(11) . . . . ?
C17 C18 C19 O1 -11.2(11) . . . . ?
C13 C18 C19 O1 171.7(9) . . . . ?
C17 C18 C19 C20 167.2(6) . . . . ?
C13 C18 C19 C20 -9.9(10) . . . . ?
O1 C19 C20 Au2 -154.7(6) . . . . ?
C18 C19 C20 Au2 26.8(7) . . . . ?
C2 C1 N1 C5 1(2) . . . . ?
C2 C1 N1 Au2 177.5(9) . . . . ?
C4 C5 N1 C1 1(3) . . . . ?
C6 C5 N1 C1 178.3(15) . . . . ?
C4 C5 N1 Au2 -175.9(14) . . . . ?
C6 C5 N1 Au2 1.6(18) . . . . ?

_refine_diff_density_max         1.470
_refine_diff_density_min         -1.788
_refine_diff_density_rms         0.146

_shelxl_version_number           2013-4


_database_code_depnum_ccdc_archive 'CCDC 1009043'
