# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H52 Ag I N8'
_chemical_formula_sum            'C42 H52 Ag I N8'
_chemical_formula_weight         903.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_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                   21.4227(11)
_cell_length_b                   8.8240(4)
_cell_length_c                   23.7341(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.380(4)
_cell_angle_gamma                90
_cell_volume                     4177.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    19115
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    1.260
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.034
0 0 1 0.108
0 -1 0 0.114
0 1 0 0.194
1 0 0 0.110
-1 0 0 0.033


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_T_max  0.866
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19021
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4705
_reflns_number_gt                3950
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0223P)²+18.8481P] 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         4705
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.5000 0.39135(5) 0.2500 0.03162(11) Uani 1 2 d S . .
I1 I 0.5000 0.73145(4) 0.2500 0.04580(12) Uani 1 2 d S . .
N4 N 0.57806(13) 0.3391(3) 0.15860(11) 0.0244(5) Uani 1 1 d . . .
N3 N 0.56667(13) 0.3008(3) 0.09901(11) 0.0261(6) Uani 1 1 d . . .
N2 N 0.47595(13) 0.2802(3) 0.12080(11) 0.0226(5) Uani 1 1 d . . .
C12 C 0.46839(16) 0.2188(4) 0.01352(14) 0.0252(7) Uani 1 1 d . . .
C1 C 0.40746(16) 0.2498(4) 0.11405(14) 0.0247(7) Uani 1 1 d . . .
C2 C 0.35732(16) 0.3514(4) 0.08210(14) 0.0263(7) Uani 1 1 d . . .
N1 N 0.32280(14) 0.6135(3) 0.04704(13) 0.0311(6) Uani 1 1 d . . .
C6 C 0.39388(19) 0.1165(4) 0.13894(16) 0.0342(8) Uani 1 1 d . . .
H6 H 0.4284 0.0520 0.1612 0.041 Uiso 1 1 d R . .
C11 C 0.50332(16) 0.2658(3) 0.07694(14) 0.0232(6) Uani 1 1 d . . .
C18 C 0.64921(16) 0.3722(4) 0.19736(14) 0.0293(7) Uani 1 1 d . . .
C7 C 0.37425(17) 0.4974(4) 0.05828(16) 0.0316(7) Uani 1 1 d . . .
H7A H 0.4159 0.5363 0.0874 0.038 Uiso 1 1 d R . .
H7B H 0.3815 0.4769 0.0210 0.038 Uiso 1 1 d R . .
C13 C 0.41996(18) 0.1049(4) -0.00275(15) 0.0325(8) Uani 1 1 d . . .
H13 H 0.4066 0.0598 0.0264 0.039 Uiso 1 1 d R . .
C17 C 0.48809(18) 0.2839(4) -0.03041(15) 0.0342(8) Uani 1 1 d . . .
H17 H 0.5196 0.3616 -0.0201 0.041 Uiso 1 1 d R . .
C3 C 0.29126(17) 0.3113(4) 0.07293(16) 0.0332(8) Uani 1 1 d . . .
H3 H 0.2564 0.3750 0.0506 0.040 Uiso 1 1 d R . .
C15 C 0.4133(2) 0.1224(5) -0.10553(16) 0.0411(9) Uani 1 1 d . . .
H15 H 0.3948 0.0895 -0.1454 0.049 Uiso 1 1 d R . .
C4 C 0.27713(19) 0.1784(5) 0.09652(18) 0.0404(9) Uani 1 1 d . . .
H4 H 0.2328 0.1534 0.0898 0.049 Uiso 1 1 d R . .
C14 C 0.39258(19) 0.0587(5) -0.06217(16) 0.0404(8) Uani 1 1 d . . .
H14 H 0.3596 -0.0158 -0.0733 0.049 Uiso 1 1 d R . .
C5 C 0.3278(2) 0.0827(4) 0.13008(18) 0.0402(9) Uani 1 1 d . . .
H5 H 0.3177 -0.0051 0.1467 0.048 Uiso 1 1 d R . .
C9 C 0.3175(2) 0.6655(5) 0.10377(17) 0.0432(9) Uani 1 1 d . . .
H9A H 0.3048 0.5821 0.1233 0.052 Uiso 1 1 d R . .
H9B H 0.2842 0.7439 0.0955 0.052 Uiso 1 1 d R . .
H9C H 0.3601 0.7045 0.1298 0.052 Uiso 1 1 d R . .
C16 C 0.4605(2) 0.2346(5) -0.08997(16) 0.0419(9) Uani 1 1 d . . .
H16 H 0.4746 0.2770 -0.1192 0.050 Uiso 1 1 d R . .
C8 C 0.3400(2) 0.7435(5) 0.0171(2) 0.0457(10) Uani 1 1 d . . .
H8A H 0.3815 0.7869 0.0433 0.055 Uiso 1 1 d R . .
H8B H 0.3051 0.8182 0.0080 0.055 Uiso 1 1 d R . .
H8C H 0.3446 0.7106 -0.0198 0.055 Uiso 1 1 d R . .
C20 C 0.6758(2) 0.4886(7) 0.1660(2) 0.0659(15) Uani 1 1 d . . .
H20A H 0.6708 0.4523 0.1264 0.079 Uiso 1 1 d R . .
H20B H 0.7225 0.5057 0.1890 0.079 Uiso 1 1 d R . .
H20C H 0.6516 0.5819 0.1623 0.079 Uiso 1 1 d R . .
C19 C 0.6536(2) 0.4273(6) 0.25861(17) 0.0529(12) Uani 1 1 d . . .
H19A H 0.6264 0.5165 0.2539 0.063 Uiso 1 1 d R . .
H19B H 0.6993 0.4512 0.2826 0.063 Uiso 1 1 d R . .
H19C H 0.6376 0.3498 0.2784 0.063 Uiso 1 1 d R . .
C21 C 0.6874(2) 0.2239(6) 0.2045(3) 0.0739(17) Uani 1 1 d . . .
H21A H 0.6646 0.1475 0.2185 0.089 Uiso 1 1 d R . .
H21B H 0.7321 0.2363 0.2334 0.089 Uiso 1 1 d R . .
H21C H 0.6892 0.1936 0.1663 0.089 Uiso 1 1 d R . .
C10 C 0.52434(16) 0.3283(4) 0.17379(13) 0.0251(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
Ag1 C10 2.131(3) . ?
Ag1 C10 2.131(3) 2_655 ?
Ag1 I1 3.0010(5) . ?
N4 C10 1.329(4) . ?
N4 N3 1.387(3) . ?
N4 C18 1.494(4) . ?
N3 C11 1.301(4) . ?
N2 C10 1.373(4) . ?
N2 C11 1.374(4) . ?
N2 C1 1.442(4) . ?
C12 C17 1.384(5) . ?
C12 C13 1.394(5) . ?
C12 C11 1.475(4) . ?
C1 C2 1.393(5) . ?
C1 C6 1.394(5) . ?
C2 C3 1.397(5) . ?
C2 C7 1.504(5) . ?
N1 C7 1.456(4) . ?
N1 C8 1.466(5) . ?
N1 C9 1.466(5) . ?
C6 C5 1.385(5) . ?
C6 H6 0.9300 . ?
C18 C20 1.499(5) . ?
C18 C19 1.503(5) . ?
C18 C21 1.520(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C13 C14 1.377(5) . ?
C13 H13 0.9299 . ?
C17 C16 1.388(5) . ?
C17 H17 0.9300 . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
C15 C16 1.367(6) . ?
C15 C14 1.380(5) . ?
C15 H15 0.9299 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9300 . ?
C14 H14 0.9301 . ?
C5 H5 0.9299 . ?
C9 H9A 0.9601 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C16 H16 0.9299 . ?
C8 H8A 0.9599 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9601 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9599 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9598 . ?
C19 H19C 0.9601 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9602 . ?

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
C10 Ag1 C10 149.74(17) . 2_655 ?
C10 Ag1 I1 105.13(9) . . ?
C10 Ag1 I1 105.13(9) 2_655 . ?
C10 N4 N3 114.3(3) . . ?
C10 N4 C18 129.6(3) . . ?
N3 N4 C18 115.9(2) . . ?
C11 N3 N4 103.8(2) . . ?
C10 N2 C11 109.5(3) . . ?
C10 N2 C1 123.9(2) . . ?
C11 N2 C1 126.6(3) . . ?
C17 C12 C13 119.4(3) . . ?
C17 C12 C11 118.1(3) . . ?
C13 C12 C11 122.3(3) . . ?
C2 C1 C6 122.4(3) . . ?
C2 C1 N2 119.5(3) . . ?
C6 C1 N2 118.1(3) . . ?
C1 C2 C3 117.3(3) . . ?
C1 C2 C7 120.8(3) . . ?
C3 C2 C7 121.9(3) . . ?
C7 N1 C8 109.4(3) . . ?
C7 N1 C9 111.1(3) . . ?
C8 N1 C9 108.5(3) . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.7 . . ?
N3 C11 N2 110.1(3) . . ?
N3 C11 C12 123.0(3) . . ?
N2 C11 C12 126.9(3) . . ?
N4 C18 C20 108.4(3) . . ?
N4 C18 C19 110.4(3) . . ?
C20 C18 C19 111.0(4) . . ?
N4 C18 C21 106.7(3) . . ?
C20 C18 C21 111.0(4) . . ?
C19 C18 C21 109.3(4) . . ?
N1 C7 C2 113.7(3) . . ?
N1 C7 H7A 108.7 . . ?
C2 C7 H7A 108.7 . . ?
N1 C7 H7B 109.1 . . ?
C2 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C12 C17 C16 120.2(3) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 119.8 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.5 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 119.9 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C13 C14 C15 120.7(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.6 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 119.8 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.7 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.2 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 120.0 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.4 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C18 C20 H20A 109.2 . . ?
C18 C20 H20B 109.3 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.9 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C21 H21A 108.8 . . ?
C18 C21 H21B 109.7 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.9 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C10 N2 102.3(2) . . ?
N4 C10 Ag1 135.7(2) . . ?
N2 C10 Ag1 121.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         1.148
_refine_diff_density_min         -1.079
_refine_diff_density_rms         0.093
_database_code_depnum_ccdc_archive 'CCDC 1011243'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 Au Cl N4, C7 H8'
_chemical_formula_sum            'C28 H34 Au Cl N4'
_chemical_formula_weight         659.01

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'

_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   14.5680(4)
_cell_length_b                   11.8901(10)
_cell_length_c                   17.5700(10)
_cell_angle_alpha                90
_cell_angle_beta                 118.093(4)
_cell_angle_gamma                90
_cell_volume                     2684.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    26420
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1304
_exptl_absorpt_coefficient_mu    5.602
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 1 0.064
0 1 -1 0.131
0 1 1 0.111
0 -1 -1 0.092
1 0 0 0.106
-1 0 0 0.088


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.314
_exptl_absorpt_correction_T_max  0.441
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26335
_diffrn_reflns_av_R_equivalents  0.1100
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6121
_reflns_number_gt                5108
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0535P)²+7.6527P] 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         6121
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.105822(15) -0.029667(18) -0.009527(12) 0.02038(9) Uani 1 1 d . . .
Cl1 Cl 0.03898(10) -0.14163(13) -0.12981(9) 0.0271(3) Uani 1 1 d . . .
C1 C 0.1334(4) 0.2528(5) 0.0193(3) 0.0192(10) Uani 1 1 d . . .
C10 C 0.1669(4) 0.0672(5) 0.0940(3) 0.0200(10) Uani 1 1 d . . .
C25 C 0.4953(5) 0.3446(7) 0.4102(4) 0.0384(15) Uani 1 1 d . . .
H25 H 0.4381 0.3923 0.3894 0.046 Uiso 1 1 d R . .
N3 N 0.2303(3) 0.1344(4) 0.2308(3) 0.0221(9) Uani 1 1 d . . .
N1 N 0.3725(4) 0.2413(5) 0.0842(3) 0.0305(11) Uani 1 1 d . . .
N2 N 0.1692(3) 0.1818(4) 0.0944(3) 0.0179(9) Uani 1 1 d . . .
C22 C 0.6688(5) 0.2032(6) 0.4701(4) 0.0274(12) Uani 1 1 d . . .
C6 C 0.0434(4) 0.3159(5) -0.0041(4) 0.0252(12) Uani 1 1 d . . .
H6 H 0.0078 0.3113 0.0280 0.030 Uiso 1 1 d R . .
C2 C 0.1907(4) 0.2593(5) -0.0258(3) 0.0220(11) Uani 1 1 d . . .
C12 C 0.2171(4) 0.3369(5) 0.2065(3) 0.0193(10) Uani 1 1 d . . .
C15 C 0.2482(6) 0.5522(6) 0.2735(4) 0.0334(14) Uani 1 1 d . . .
H15 H 0.2595 0.6242 0.2970 0.040 Uiso 1 1 d R . .
N4 N 0.2059(4) 0.0407(4) 0.1778(3) 0.0207(9) Uani 1 1 d . . .
C7 C 0.2910(4) 0.1952(5) 0.0040(4) 0.0260(12) Uani 1 1 d . . .
H7A H 0.2798 0.1166 0.0120 0.031 Uiso 1 1 d R . .
H7B H 0.3132 0.1997 -0.0400 0.031 Uiso 1 1 d R . .
C11 C 0.2058(4) 0.2195(5) 0.1779(3) 0.0184(10) Uani 1 1 d . . .
C4 C 0.0624(5) 0.3914(6) -0.1219(4) 0.0328(14) Uani 1 1 d . . .
H4 H 0.0383 0.4372 -0.1704 0.039 Uiso 1 1 d R . .
C8 C 0.4204(6) 0.3406(6) 0.0678(6) 0.0445(17) Uani 1 1 d . . .
H8A H 0.4653 0.3771 0.1213 0.053 Uiso 1 1 d R . .
H8B H 0.3667 0.3918 0.0312 0.053 Uiso 1 1 d R . .
H8C H 0.4602 0.3178 0.0397 0.053 Uiso 1 1 d R . .
C27 C 0.6735(5) 0.3064(6) 0.5085(4) 0.0285(13) Uani 1 1 d . . .
H27 H 0.7354 0.3290 0.5554 0.034 Uiso 1 1 d R . .
C23 C 0.5733(5) 0.1708(6) 0.4013(4) 0.0325(13) Uani 1 1 d . . .
H23 H 0.5675 0.1018 0.3744 0.039 Uiso 1 1 d R . .
C17 C 0.2767(4) 0.4127(5) 0.1885(4) 0.0244(11) Uani 1 1 d . . .
H17 H 0.3064 0.3907 0.1542 0.029 Uiso 1 1 d R . .
C13 C 0.1716(5) 0.3693(5) 0.2571(4) 0.0264(12) Uani 1 1 d . . .
H13 H 0.1308 0.3191 0.2688 0.032 Uiso 1 1 d R . .
C3 C 0.1520(5) 0.3299(5) -0.0974(4) 0.0285(13) Uani 1 1 d . . .
H3 H 0.1879 0.3359 -0.1291 0.034 Uiso 1 1 d R . .
C24 C 0.4882(5) 0.2402(7) 0.3723(5) 0.0431(17) Uani 1 1 d . . .
H24 H 0.4250 0.2166 0.3274 0.052 Uiso 1 1 d R . .
C16 C 0.2920(5) 0.5212(5) 0.2216(4) 0.0308(13) Uani 1 1 d . . .
H16 H 0.3309 0.5728 0.2090 0.037 Uiso 1 1 d R . .
C26 C 0.5874(5) 0.3755(6) 0.4776(4) 0.0348(14) Uani 1 1 d . . .
H26 H 0.5929 0.4450 0.5037 0.042 Uiso 1 1 d R . .
C18 C 0.2229(5) -0.0736(5) 0.2185(4) 0.0275(12) Uani 1 1 d . . .
C14 C 0.1887(6) 0.4776(6) 0.2905(4) 0.0329(15) Uani 1 1 d . . .
H14 H 0.1590 0.5000 0.3249 0.039 Uiso 1 1 d R . .
C5 C 0.0082(5) 0.3863(6) -0.0754(4) 0.0312(13) Uani 1 1 d . . .
H5 H -0.0516 0.4291 -0.0920 0.037 Uiso 1 1 d R . .
C28 C 0.7636(5) 0.1299(7) 0.5008(5) 0.0399(16) Uani 1 1 d . . .
H28A H 0.8126 0.1497 0.5589 0.048 Uiso 1 1 d R . .
H28B H 0.7950 0.1404 0.4640 0.048 Uiso 1 1 d R . .
H28C H 0.7436 0.0526 0.4989 0.048 Uiso 1 1 d R . .
C21 C 0.2893(6) -0.0601(6) 0.3151(4) 0.0382(16) Uani 1 1 d . . .
H21A H 0.3525 -0.0216 0.3267 0.046 Uiso 1 1 d R . .
H21B H 0.3058 -0.1331 0.3416 0.046 Uiso 1 1 d R . .
H21C H 0.2522 -0.0175 0.3383 0.046 Uiso 1 1 d R . .
C9 C 0.4524(6) 0.1589(8) 0.1329(5) 0.0472(19) Uani 1 1 d . . .
H9A H 0.4204 0.0916 0.1394 0.057 Uiso 1 1 d R . .
H9B H 0.4983 0.1892 0.1887 0.057 Uiso 1 1 d R . .
H9C H 0.4914 0.1416 0.1030 0.057 Uiso 1 1 d R . .
C19 C 0.2831(8) -0.1448(7) 0.1850(5) 0.058(2) Uani 1 1 d . . .
H19A H 0.2406 -0.1578 0.1244 0.069 Uiso 1 1 d R . .
H19B H 0.3009 -0.2154 0.2150 0.069 Uiso 1 1 d R . .
H19C H 0.3456 -0.1063 0.1945 0.069 Uiso 1 1 d R . .
C20 C 0.1187(6) -0.1237(7) 0.1980(6) 0.052(2) Uani 1 1 d . . .
H20A H 0.0824 -0.0741 0.2179 0.063 Uiso 1 1 d R . .
H20B H 0.1289 -0.1952 0.2262 0.063 Uiso 1 1 d R . .
H20C H 0.0783 -0.1337 0.1367 0.063 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C10 1.976(5) . ?
Au1 Cl1 2.2910(14) . ?
Au1 Au1 3.3299(4) 3 ?
C1 C6 1.394(8) . ?
C1 C2 1.397(8) . ?
C1 N2 1.443(7) . ?
C10 N4 1.342(7) . ?
C10 N2 1.363(7) . ?
C25 C26 1.357(10) . ?
C25 C24 1.389(11) . ?
C25 H25 0.9300 . ?
N3 C11 1.305(7) . ?
N3 N4 1.386(7) . ?
N1 C9 1.452(10) . ?
N1 C7 1.456(8) . ?
N1 C8 1.467(10) . ?
N2 C11 1.378(6) . ?
C22 C27 1.385(9) . ?
C22 C23 1.401(8) . ?
C22 C28 1.501(9) . ?
C6 C5 1.389(8) . ?
C6 H6 0.9300 . ?
C2 C3 1.392(8) . ?
C2 C7 1.507(8) . ?
C12 C17 1.387(8) . ?
C12 C13 1.391(8) . ?
C12 C11 1.467(8) . ?
C15 C14 1.369(10) . ?
C15 C16 1.386(9) . ?
C15 H15 0.9299 . ?
N4 C18 1.501(7) . ?
C7 H7A 0.9699 . ?
C7 H7B 0.9699 . ?
C4 C3 1.376(9) . ?
C4 C5 1.379(9) . ?
C4 H4 0.9301 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9601 . ?
C27 C26 1.380(9) . ?
C27 H27 0.9300 . ?
C23 C24 1.372(10) . ?
C23 H23 0.9301 . ?
C17 C16 1.390(8) . ?
C17 H17 0.9299 . ?
C13 C14 1.388(9) . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C24 H24 0.9301 . ?
C16 H16 0.9301 . ?
C26 H26 0.9300 . ?
C18 C20 1.508(10) . ?
C18 C21 1.515(8) . ?
C18 C19 1.523(9) . ?
C14 H14 0.9299 . ?
C5 H5 0.9300 . ?
C28 H28A 0.9599 . ?
C28 H28B 0.9599 . ?
C28 H28C 0.9601 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9601 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C10 Au1 Cl1 178.48(15) . . ?
C10 Au1 Au1 79.69(15) . 3 ?
Cl1 Au1 Au1 101.80(4) . 3 ?
C6 C1 C2 122.2(5) . . ?
C6 C1 N2 118.0(5) . . ?
C2 C1 N2 119.7(5) . . ?
N4 C10 N2 103.4(4) . . ?
N4 C10 Au1 130.3(4) . . ?
N2 C10 Au1 125.9(4) . . ?
C26 C25 C24 118.7(7) . . ?
C26 C25 H25 120.8 . . ?
C24 C25 H25 120.5 . . ?
C11 N3 N4 104.3(4) . . ?
C9 N1 C7 112.2(6) . . ?
C9 N1 C8 109.6(6) . . ?
C7 N1 C8 111.1(5) . . ?
C10 N2 C11 109.1(4) . . ?
C10 N2 C1 125.7(4) . . ?
C11 N2 C1 125.2(5) . . ?
C27 C22 C23 117.7(6) . . ?
C27 C22 C28 120.9(6) . . ?
C23 C22 C28 121.4(6) . . ?
C5 C6 C1 119.1(5) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.3 . . ?
C3 C2 C1 116.7(5) . . ?
C3 C2 C7 122.2(5) . . ?
C1 C2 C7 121.1(5) . . ?
C17 C12 C13 120.2(5) . . ?
C17 C12 C11 121.5(5) . . ?
C13 C12 C11 118.2(5) . . ?
C14 C15 C16 120.4(6) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.7 . . ?
C10 N4 N3 112.9(5) . . ?
C10 N4 C18 128.7(5) . . ?
N3 N4 C18 118.3(5) . . ?
N1 C7 C2 111.1(5) . . ?
N1 C7 H7A 109.8 . . ?
C2 C7 H7A 109.6 . . ?
N1 C7 H7B 109.0 . . ?
C2 C7 H7B 109.2 . . ?
H7A C7 H7B 108.1 . . ?
N3 C11 N2 110.2(5) . . ?
N3 C11 C12 123.1(5) . . ?
N2 C11 C12 126.8(5) . . ?
C3 C4 C5 120.9(6) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.6 . . ?
N1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.2 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.4 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C26 C27 C22 120.6(6) . . ?
C26 C27 H27 119.9 . . ?
C22 C27 H27 119.5 . . ?
C24 C23 C22 120.7(6) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.9 . . ?
C12 C17 C16 120.1(5) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 120.0 . . ?
C14 C13 C12 118.9(6) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.6 . . ?
C4 C3 C2 121.6(6) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.0 . . ?
C23 C24 C25 120.6(6) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.8 . . ?
C15 C16 C17 119.3(6) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.5 . . ?
C25 C26 C27 121.6(7) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.0 . . ?
N4 C18 C20 108.8(5) . . ?
N4 C18 C21 108.2(5) . . ?
C20 C18 C21 110.5(6) . . ?
N4 C18 C19 108.3(5) . . ?
C20 C18 C19 112.8(7) . . ?
C21 C18 C19 108.2(6) . . ?
C15 C14 C13 120.9(6) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.6 . . ?
C4 C5 C6 119.4(6) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C22 C28 H28A 109.7 . . ?
C22 C28 H28B 109.4 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 109.3 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C18 C21 H21A 109.3 . . ?
C18 C21 H21B 109.2 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.9 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.2 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.8 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.9 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.6 . . ?
C18 C20 H20B 109.4 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         4.333
_refine_diff_density_min         -2.438
_refine_diff_density_rms         0.203
_database_code_depnum_ccdc_archive 'CCDC 1011244'
#######################################################################
#
#                 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_jt130314au1
_audit_creation_date             2014-06-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H26 Au Br N4, 1(C6 H6)'
_chemical_formula_sum            'C27 H32 Au Br N4'
_chemical_formula_weight         689.44
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0130 8.8020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
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                   19.9850(5)
_cell_length_b                   8.5330(18)
_cell_length_c                   31.1480(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5311.7(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.252
_shelx_estimated_absorpt_T_min   0.175
_exptl_absorpt_coefficient_mu    7.065
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.587972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.1352 before and 0.0404 after correction.
The Ratio of minimum to maximum transmission is 0.5880.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.269
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1523
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            46503
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         4.079
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                9472
_reflns_number_total             10365
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         2.174
_refine_diff_density_min         -2.148
_refine_diff_density_rms         0.196
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         10365
_refine_ls_number_restraints     583
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²+35.4133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1212
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H21A,H21B,H21C} of C21, {H19A,H19B,H19C} of C19, {H20J,
  H20K,H20L} of C20, {H9A,H9B,H9C} of C9, {H10D,H10E,H10F} of C109, {H10A,H10B,
  H10C} of C108, {H8A,H8B,H8C} of C8, All C(H,H) groups
 At 1.5 times of:
  {H12D,H12E,H12F} of C120, {H11A,H11B,H11C} of C119, {H12A,H12B,H12C} of
  C121, {H20A,H20B,H20C} of C202, {H20D,H20E,H20F} of C200, {H20G,H20H,H20I} of
  C201
2. Restrained distances
 C118-C200 = C118-C119 = C118-C201 = C118-C120 = C118-C202 = C118-C121
 1.54 with sigma of 0.01
 C119-C120 \\sim C119-C121 \\sim C120-C121 \\sim C200-C201 \\sim C200-C202
\\sim C201-C202
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C119) = Uanis(C200)
Uanis(C120) = Uanis(C201)
Uanis(C121) = Uanis(C202)
Uanis(C21) = Uanis(C120)
Uanis(C21) = Uanis(C121)
Uanis(C118) = Uanis(C18)
Uanis(C33) = Uanis(C133)
Uanis(C32) = Uanis(C132)
Uanis(C31) = Uanis(C131)
Uanis(C30) = Uanis(C130)
Uanis(C29) = Uanis(C129)
Uanis(C28) = Uanis(C128)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C128)=Sof(H128)=Sof(C129)=Sof(H129)=Sof(C130)=Sof(H130)=Sof(C131)=
 Sof(H131)=Sof(C132)=Sof(H132)=Sof(C133)=Sof(H133)=1-FVAR(1)
 Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=
 Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=FVAR(1)
 Fixed Sof: C121(0.7) H12A(0.7) H12B(0.7) H12C(0.7) C119(0.5) H11A(0.5)
 H11B(0.5) H11C(0.5) C120(0.6) H12D(0.6) H12E(0.6) H12F(0.6) C202(0.3)
 H20A(0.3) H20B(0.3) H20C(0.3) C200(0.5) H20D(0.5) H20E(0.5) H20F(0.5)
 C201(0.4) H20G(0.4) H20H(0.4) H20I(0.4)
6.a Riding coordinates:
 C104(H104), C6(H6), C105(H105), C108(H10A,H10B,H10C), C13(H13), C106(H106),
 C5(H5), C114(H114), C8(H8A,H8B,H8C), C4(H4), C14(H14), C15(H15), C117(H117),
 C113(H113), C7(H7A,H7B), C116(H116), C17(H17), C115(H115), C103(H103),
 C109(H10D,H10E,H10F), C107(H10G,H10H), C16(H16), C3(H3), C9(H9A,H9B,H9C),
 C21(H21A,H21B,H21C), C19(H19A,H19B,H19C), C20(H20J,H20K,H20L)
6.b Me refined with riding coordinates:
 C121(H12A,H12B,H12C), C119(H11A,H11B,H11C), C120(H12D,H12E,H12F), C202(H20A,
 H20B,H20C), C200(H20D,H20E,H20F), C201(H20G,H20H,H20I)
6.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
 C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C128(H128), C129(H129),
 C130(H130), C131(H131), C132(H132), C133(H133)
6.d Fitted hexagon refined as free rotating group:
 C22(C23,C24,C25,C26,C27), C28(C29,C30,C31,C32,C33), C128(C129,C130,C131,C132,
 C133)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.59387(2) 0.23082(5) -0.10513(2) 0.02121(13) Uani 1 1 d . . . . .
Au2 Au 0.72375(2) 0.47248(6) -0.08089(2) 0.02257(14) Uani 1 1 d . . . . .
Br1 Br 0.56983(8) 0.1509(2) -0.03325(6) 0.0360(4) Uani 1 1 d . . . . .
Br2 Br 0.74370(8) 0.5591(2) -0.15287(6) 0.0357(4) Uani 1 1 d . . . . .
C104 C 0.8864(8) -0.0062(18) -0.0521(5) 0.026(3) Uani 1 1 d . . . . .
H104 H 0.9177 -0.0773 -0.0626 0.031 Uiso 1 1 d R . . . .
N8 N 0.6475(6) 0.2062(12) -0.1950(4) 0.016(2) Uani 1 1 d . . . . .
C102 C 0.8625(7) 0.2235(15) -0.0098(5) 0.018(2) Uani 1 1 d . . . . .
N6 N 0.5823(5) 0.4021(13) -0.1889(4) 0.017(2) Uani 1 1 d . . . . .
N4 N 0.6769(6) 0.4868(14) 0.0123(4) 0.023(2) Uani 1 1 d . . . . .
N2 N 0.7454(6) 0.2990(13) 0.0011(4) 0.016(2) Uani 1 1 d . . . . .
N3 N 0.6873(6) 0.4208(15) 0.0512(4) 0.023(2) Uani 1 1 d . . . . .
C118 C 0.6335(6) 0.6282(15) 0.0092(4) 0.0257(19) Uani 1 1 d D . . . .
C111 C 0.7289(7) 0.3042(17) 0.0441(5) 0.020(3) Uani 1 1 d . . . . .
N7 N 0.6452(6) 0.2734(13) -0.2353(4) 0.019(2) Uani 1 1 d . . . . .
N5 N 0.4628(7) 0.1960(15) -0.1972(4) 0.028(3) Uani 1 1 d . . . . .
C2 C 0.4649(7) 0.4816(16) -0.1841(5) 0.020(3) Uani 1 1 d . . . . .
C110 C 0.7118(6) 0.4174(16) -0.0191(5) 0.017(2) Uani 1 1 d . . . . .
C6 C 0.5501(7) 0.6197(16) -0.1430(5) 0.023(3) Uani 1 1 d . . . . .
H6 H 0.5945 0.6296 -0.1346 0.028 Uiso 1 1 d R . . . .
C105 C 0.8187(8) -0.0281(16) -0.0614(5) 0.023(3) Uani 1 1 d . . . . .
H105 H 0.8054 -0.1101 -0.0791 0.027 Uiso 1 1 d R . . . .
C108 C 0.8922(9) 0.5442(19) -0.0412(6) 0.035(4) Uani 1 1 d . . . . .
H10A H 0.9392 0.5625 -0.0370 0.042 Uiso 1 1 d R . . . .
H10B H 0.8719 0.6364 -0.0531 0.042 Uiso 1 1 d R . . . .
H10C H 0.8862 0.4577 -0.0605 0.042 Uiso 1 1 d R . . . .
C12 C 0.5890(7) 0.5017(18) -0.2663(5) 0.022(3) Uani 1 1 d . . . . .
C11 C 0.6056(7) 0.3927(17) -0.2307(5) 0.021(3) Uani 1 1 d . . . . .
C13 C 0.5764(8) 0.6572(19) -0.2605(6) 0.029(3) Uani 1 1 d . . . . .
H13 H 0.5751 0.6979 -0.2328 0.035 Uiso 1 1 d R . . . .
C112 C 0.7547(7) 0.2030(17) 0.0789(5) 0.022(3) Uani 1 1 d . . . . .
C106 C 0.7716(7) 0.0751(16) -0.0437(5) 0.020(3) Uani 1 1 d . . . . .
H106 H 0.7261 0.0603 -0.0487 0.024 Uiso 1 1 d R . . . .
N1 N 0.8630(7) 0.5108(14) -0.0001(5) 0.027(3) Uani 1 1 d . . . . .
C5 C 0.5019(7) 0.7189(17) -0.1269(5) 0.024(3) Uani 1 1 d . . . . .
H5 H 0.5140 0.7975 -0.1077 0.028 Uiso 1 1 d R . . . .
C114 C 0.7915(10) -0.0461(19) 0.1062(6) 0.036(4) Uani 1 1 d . . . . .
H114 H 0.8019 -0.1511 0.1017 0.043 Uiso 1 1 d R . . . .
C8 C 0.4498(11) 0.074(2) -0.2290(6) 0.042(4) Uani 1 1 d . . . . .
H8A H 0.4035 0.0777 -0.2371 0.051 Uiso 1 1 d R . . . .
H8B H 0.4598 -0.0259 -0.2166 0.051 Uiso 1 1 d R . . . .
H8C H 0.4772 0.0901 -0.2540 0.051 Uiso 1 1 d R . . . .
C4 C 0.4361(8) 0.7021(18) -0.1390(6) 0.029(3) Uani 1 1 d . . . . .
H4 H 0.4038 0.7708 -0.1286 0.034 Uiso 1 1 d R . . . .
C101 C 0.7936(7) 0.1974(16) -0.0187(4) 0.018(2) Uani 1 1 d . . . . .
C14 C 0.5656(9) 0.755(2) -0.2947(6) 0.036(3) Uani 1 1 d . . . . .
H14 H 0.5567 0.8612 -0.2904 0.043 Uiso 1 1 d R . . . .
C1 C 0.5312(7) 0.5012(16) -0.1718(5) 0.020(3) Uani 1 1 d . . . . .
C15 C 0.5682(9) 0.699(2) -0.3364(6) 0.037(3) Uani 1 1 d . . . . .
H15 H 0.5616 0.7643 -0.3598 0.044 Uiso 1 1 d R . . . .
C117 C 0.7583(8) 0.2620(19) 0.1198(5) 0.027(3) Uani 1 1 d . . . . .
H117 H 0.7463 0.3657 0.1249 0.033 Uiso 1 1 d R . . . .
C113 C 0.7720(9) 0.0470(17) 0.0715(5) 0.029(3) Uani 1 1 d . . . . .
H113 H 0.7710 0.0065 0.0438 0.035 Uiso 1 1 d R . . . .
C18 C 0.6906(8) 0.0610(17) -0.1883(5) 0.0257(19) Uani 1 1 d . . . . .
C7 C 0.4437(8) 0.3490(17) -0.2134(5) 0.026(3) Uani 1 1 d . . . . .
H7A H 0.3954 0.3521 -0.2165 0.031 Uiso 1 1 d R . . . .
H7B H 0.4631 0.3642 -0.2417 0.031 Uiso 1 1 d R . . . .
C116 C 0.7798(9) 0.173(2) 0.1534(5) 0.031(3) Uani 1 1 d . . . . .
H116 H 0.7833 0.2159 0.1808 0.037 Uiso 1 1 d R . . . .
C17 C 0.5914(8) 0.4421(18) -0.3080(5) 0.027(3) Uani 1 1 d . . . . .
H17 H 0.6007 0.3365 -0.3125 0.032 Uiso 1 1 d R . . . .
C115 C 0.7954(9) 0.016(2) 0.1468(6) 0.034(3) Uani 1 1 d . . . . .
H115 H 0.8087 -0.0459 0.1697 0.041 Uiso 1 1 d R . . . .
C103 C 0.9076(7) 0.1165(17) -0.0281(5) 0.023(3) Uani 1 1 d . . . . .
H103 H 0.9533 0.1298 -0.0236 0.028 Uiso 1 1 d R . . . .
C109 C 0.8744(11) 0.634(2) 0.0316(6) 0.043(4) Uani 1 1 d . . . . .
H10D H 0.9205 0.6327 0.0404 0.051 Uiso 1 1 d R . . . .
H10E H 0.8463 0.6176 0.0561 0.051 Uiso 1 1 d R . . . .
H10F H 0.8642 0.7338 0.0189 0.051 Uiso 1 1 d R . . . .
C107 C 0.8850(7) 0.3601(16) 0.0170(5) 0.022(3) Uani 1 1 d . . . . .
H10G H 0.8675 0.3477 0.0458 0.027 Uiso 1 1 d R . . . .
H10H H 0.9335 0.3600 0.0187 0.027 Uiso 1 1 d R . . . .
C16 C 0.5802(9) 0.538(2) -0.3426(6) 0.035(3) Uani 1 1 d . . . . .
H16 H 0.5807 0.4971 -0.3702 0.042 Uiso 1 1 d R . . . .
C3 C 0.4184(7) 0.5828(18) -0.1674(5) 0.025(3) Uani 1 1 d . . . . .
H3 H 0.3737 0.5722 -0.1752 0.030 Uiso 1 1 d R . . . .
C9 C 0.4262(10) 0.1591(19) -0.1577(6) 0.036(4) Uani 1 1 d . . . . .
H9A H 0.4560 0.1689 -0.1337 0.043 Uiso 1 1 d R . . . .
H9B H 0.4093 0.0539 -0.1591 0.043 Uiso 1 1 d R . . . .
H9C H 0.3895 0.2308 -0.1544 0.043 Uiso 1 1 d R . . . .
C10 C 0.6102(7) 0.2778(16) -0.1665(5) 0.017(2) Uani 1 1 d . . . . .
C21 C 0.7136(10) 0.003(2) -0.2320(6) 0.037(2) Uani 1 1 d . . . . .
H21A H 0.6755 -0.0305 -0.2483 0.044 Uiso 1 1 d R . . . .
H21B H 0.7438 -0.0833 -0.2283 0.044 Uiso 1 1 d R . . . .
H21C H 0.7360 0.0861 -0.2471 0.044 Uiso 1 1 d R . . . .
C19 C 0.7498(10) 0.110(2) -0.1596(7) 0.047(5) Uani 1 1 d . . . . .
H19A H 0.7756 0.0197 -0.1514 0.057 Uiso 1 1 d R . . . .
H19B H 0.7334 0.1616 -0.1343 0.057 Uiso 1 1 d R . . . .
H19C H 0.7775 0.1807 -0.1756 0.057 Uiso 1 1 d R . . . .
C20 C 0.6476(12) -0.062(2) -0.1665(8) 0.054(5) Uani 1 1 d . . . . .
H20J H 0.6121 -0.0889 -0.1859 0.065 Uiso 1 1 d R . . . .
H20K H 0.6291 -0.0220 -0.1403 0.065 Uiso 1 1 d R . . . .
H20L H 0.6740 -0.1533 -0.1606 0.065 Uiso 1 1 d R . . . .
C121 C 0.6027(11) 0.657(3) -0.0350(5) 0.037(2) Uani 0.7 1 d D . P A 1
H12A H 0.5750 0.7517 -0.0341 0.055 Uiso 0.7 1 calc R . P A 1
H12B H 0.6384 0.6704 -0.0562 0.055 Uiso 0.7 1 calc R . P A 1
H12C H 0.5748 0.5670 -0.0430 0.055 Uiso 0.7 1 calc R . P A 1
C119 C 0.6776(15) 0.765(3) 0.0243(10) 0.040(5) Uani 0.5 1 d D . P A 1
H11A H 0.6517 0.8629 0.0230 0.060 Uiso 0.5 1 calc R . P A 1
H11B H 0.6923 0.7467 0.0538 0.060 Uiso 0.5 1 calc R . P A 1
H11C H 0.7167 0.7742 0.0055 0.060 Uiso 0.5 1 calc R . P A 1
C120 C 0.5770(11) 0.600(3) 0.0427(7) 0.037(2) Uani 0.6 1 d D . P A 1
H12D H 0.5462 0.6896 0.0425 0.055 Uiso 0.6 1 calc R . P A 1
H12E H 0.5526 0.5045 0.0353 0.055 Uiso 0.6 1 calc R . P A 1
H12F H 0.5967 0.5892 0.0713 0.055 Uiso 0.6 1 calc R . P A 1
C202 C 0.5799(17) 0.599(6) -0.0256(10) 0.037(2) Uani 0.3 1 d D . P A 2
H20A H 0.5509 0.6916 -0.0279 0.055 Uiso 0.3 1 calc R . P A 2
H20B H 0.6018 0.5801 -0.0532 0.055 Uiso 0.3 1 calc R . P A 2
H20C H 0.5529 0.5078 -0.0177 0.055 Uiso 0.3 1 calc R . P A 2
C200 C 0.6819(15) 0.758(3) -0.0059(11) 0.040(5) Uani 0.5 1 d D . P A 2
H20D H 0.6573 0.8571 -0.0088 0.060 Uiso 0.5 1 calc R . P A 2
H20E H 0.7178 0.7711 0.0153 0.060 Uiso 0.5 1 calc R . P A 2
H20F H 0.7012 0.7292 -0.0337 0.060 Uiso 0.5 1 calc R . P A 2
C201 C 0.5997(18) 0.675(5) 0.0516(8) 0.037(2) Uani 0.4 1 d D . P A 2
H20G H 0.5722 0.7686 0.0469 0.055 Uiso 0.4 1 calc R . P A 2
H20H H 0.5714 0.5888 0.0616 0.055 Uiso 0.4 1 calc R . P A 2
H20I H 0.6340 0.6977 0.0732 0.055 Uiso 0.4 1 calc R . P A 2
C22 C 0.5446(9) 1.1159(16) 0.0797(4) 0.067(5) Uani 1 1 d . . . B 2
H22 H 0.5561 1.1915 0.0585 0.080 Uiso 1 1 calc R . . B 2
C23 C 0.5850(7) 1.0965(18) 0.1157(5) 0.065(5) Uani 1 1 d G . . B 2
H23 H 0.6240 1.1589 0.1191 0.078 Uiso 1 1 calc R . . B 2
C24 C 0.5683(7) 0.986(2) 0.1466(4) 0.064(6) Uani 1 1 d G . . B 2
H24 H 0.5958 0.9727 0.1712 0.077 Uiso 1 1 calc R . . B 2
C25 C 0.5112(8) 0.8947(16) 0.1416(5) 0.061(5) Uani 1 1 d G . . B 2
H25 H 0.4997 0.8191 0.1628 0.073 Uiso 1 1 calc R . . B 2
C26 C 0.4708(7) 0.9140(16) 0.1057(5) 0.063(5) Uani 1 1 d G . . B 2
H26 H 0.4318 0.8517 0.1022 0.076 Uiso 1 1 calc R . . B 2
C27 C 0.4875(8) 1.0246(18) 0.0747(4) 0.065(5) Uani 1 1 d G . . B 2
H27 H 0.4599 1.0379 0.0501 0.078 Uiso 1 1 calc R . . B 2
C28 C 0.2225(9) 0.393(3) 0.2031(10) 0.042(5) Uani 0.648(19) 1 d . . P C 1
H28 H 0.2609 0.3286 0.2062 0.050 Uiso 0.648(19) 1 calc R . P C 1
C29 C 0.1743(14) 0.357(2) 0.1725(8) 0.042(6) Uani 0.648(19) 1 d G . P C 1
H29 H 0.1798 0.2677 0.1546 0.051 Uiso 0.648(19) 1 calc R . P C 1
C30 C 0.1181(11) 0.452(3) 0.1680(6) 0.039(5) Uani 0.648(19) 1 d G . P C 1
H30 H 0.0852 0.4268 0.1471 0.047 Uiso 0.648(19) 1 calc R . P C 1
C31 C 0.1101(9) 0.582(3) 0.1941(9) 0.040(5) Uani 0.648(19) 1 d G . P C 1
H31 H 0.0717 0.6468 0.1911 0.048 Uiso 0.648(19) 1 calc R . P C 1
C32 C 0.1583(14) 0.618(2) 0.2248(7) 0.033(5) Uani 0.648(19) 1 d G . P C 1
H32 H 0.1528 0.7077 0.2426 0.040 Uiso 0.648(19) 1 calc R . P C 1
C33 C 0.2145(10) 0.524(3) 0.2293(6) 0.038(5) Uani 0.648(19) 1 d G . P C 1
H33 H 0.2474 0.5486 0.2502 0.046 Uiso 0.648(19) 1 calc R . P C 1
C128 C 0.204(2) 0.358(4) 0.1879(17) 0.042(5) Uani 0.352(19) 1 d . . P C 2
H128 H 0.2275 0.2661 0.1799 0.050 Uiso 0.352(19) 1 calc R . P C 2
C129 C 0.146(3) 0.399(5) 0.1662(11) 0.042(6) Uani 0.352(19) 1 d G . P C 2
H129 H 0.1296 0.3359 0.1433 0.051 Uiso 0.352(19) 1 calc R . P C 2
C130 C 0.1108(15) 0.534(6) 0.1779(15) 0.039(5) Uani 0.352(19) 1 d G . P C 2
H130 H 0.0710 0.5621 0.1631 0.047 Uiso 0.352(19) 1 calc R . P C 2
C131 C 0.134(2) 0.627(4) 0.2114(16) 0.040(5) Uani 0.352(19) 1 d G . P C 2
H131 H 0.1103 0.7185 0.2194 0.048 Uiso 0.352(19) 1 calc R . P C 2
C132 C 0.192(3) 0.585(5) 0.2331(10) 0.033(5) Uani 0.352(19) 1 d G . P C 2
H132 H 0.2082 0.6488 0.2560 0.040 Uiso 0.352(19) 1 calc R . P C 2
C133 C 0.2271(15) 0.451(6) 0.2214(15) 0.038(5) Uani 0.352(19) 1 d G . P C 2
H133 H 0.2668 0.4226 0.2362 0.046 Uiso 0.352(19) 1 calc R . P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 Br1 2.3892(18) . ?
Au1 C10 1.979(14) . ?
Au2 Br2 2.3942(18) . ?
Au2 C110 1.996(14) . ?
C104 H104 0.9300 . ?
C104 C105 1.40(2) . ?
C104 C103 1.35(2) . ?
N8 N7 1.382(16) . ?
N8 C18 1.523(17) . ?
N8 C10 1.311(18) . ?
C102 C101 1.423(19) . ?
C102 C103 1.40(2) . ?
C102 C107 1.50(2) . ?
N6 C11 1.385(19) . ?
N6 C1 1.429(18) . ?
N6 C10 1.388(18) . ?
N4 N3 1.352(18) . ?
N4 C118 1.489(17) . ?
N4 C110 1.337(19) . ?
N2 C111 1.380(19) . ?
N2 C110 1.366(18) . ?
N2 C101 1.434(18) . ?
N3 C111 1.315(19) . ?
C118 C121 1.529(12) . ?
C118 C119 1.538(13) . ?
C118 C120 1.554(13) . ?
C118 C202 1.545(13) . ?
C118 C200 1.546(13) . ?
C118 C201 1.534(13) . ?
C111 C112 1.48(2) . ?
N7 C11 1.297(18) . ?
N5 C8 1.46(2) . ?
N5 C7 1.451(19) . ?
N5 C9 1.46(2) . ?
C2 C1 1.391(19) . ?
C2 C7 1.51(2) . ?
C2 C3 1.37(2) . ?
C6 H6 0.9301 . ?
C6 C5 1.38(2) . ?
C6 C1 1.40(2) . ?
C105 H105 0.9301 . ?
C105 C106 1.40(2) . ?
C108 H10A 0.9603 . ?
C108 H10B 0.9600 . ?
C108 H10C 0.9597 . ?
C108 N1 1.43(2) . ?
C12 C11 1.48(2) . ?
C12 C13 1.36(2) . ?
C12 C17 1.39(2) . ?
C13 H13 0.9301 . ?
C13 C14 1.37(2) . ?
C112 C117 1.37(2) . ?
C112 C113 1.39(2) . ?
C106 H106 0.9300 . ?
C106 C101 1.38(2) . ?
N1 C109 1.46(2) . ?
N1 C107 1.459(18) . ?
C5 H5 0.9300 . ?
C5 C4 1.37(2) . ?
C114 H114 0.9301 . ?
C114 C113 1.40(2) . ?
C114 C115 1.37(3) . ?
C8 H8A 0.9599 . ?
C8 H8B 0.9601 . ?
C8 H8C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C3 1.40(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.39(3) . ?
C15 H15 0.9297 . ?
C15 C16 1.41(3) . ?
C117 H117 0.9300 . ?
C117 C116 1.36(2) . ?
C113 H113 0.9304 . ?
C18 C21 1.52(2) . ?
C18 C19 1.54(2) . ?
C18 C20 1.52(3) . ?
C7 H7A 0.9696 . ?
C7 H7B 0.9703 . ?
C116 H116 0.9299 . ?
C116 C115 1.39(2) . ?
C17 H17 0.9298 . ?
C17 C16 1.37(2) . ?
C115 H115 0.9301 . ?
C103 H103 0.9303 . ?
C109 H10D 0.9601 . ?
C109 H10E 0.9599 . ?
C109 H10F 0.9600 . ?
C107 H10G 0.9699 . ?
C107 H10H 0.9698 . ?
C16 H16 0.9296 . ?
C3 H3 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9599 . ?
C21 H21A 0.9603 . ?
C21 H21B 0.9602 . ?
C21 H21C 0.9601 . ?
C19 H19A 0.9599 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9599 . ?
C20 H20J 0.9604 . ?
C20 H20K 0.9598 . ?
C20 H20L 0.9599 . ?
C121 H12A 0.9800 . ?
C121 H12B 0.9800 . ?
C121 H12C 0.9800 . ?
C119 H11A 0.9800 . ?
C119 H11B 0.9800 . ?
C119 H11C 0.9800 . ?
C120 H12D 0.9800 . ?
C120 H12E 0.9800 . ?
C120 H12F 0.9800 . ?
C202 H20A 0.9800 . ?
C202 H20B 0.9800 . ?
C202 H20C 0.9800 . ?
C200 H20D 0.9800 . ?
C200 H20E 0.9800 . ?
C200 H20F 0.9800 . ?
C201 H20G 0.9800 . ?
C201 H20H 0.9800 . ?
C201 H20I 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.3900 . ?
C22 C27 1.3900 . ?
C23 H23 0.9500 . ?
C23 C24 1.3900 . ?
C24 H24 0.9500 . ?
C24 C25 1.3900 . ?
C25 H25 0.9500 . ?
C25 C26 1.3900 . ?
C26 H26 0.9500 . ?
C26 C27 1.3900 . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.3900 . ?
C28 C33 1.3900 . ?
C29 H29 0.9500 . ?
C29 C30 1.3900 . ?
C30 H30 0.9500 . ?
C30 C31 1.3900 . ?
C31 H31 0.9500 . ?
C31 C32 1.3900 . ?
C32 H32 0.9500 . ?
C32 C33 1.3900 . ?
C33 H33 0.9500 . ?
C128 H128 0.9500 . ?
C128 C129 1.3900 . ?
C128 C133 1.3900 . ?
C129 H129 0.9500 . ?
C129 C130 1.3900 . ?
C130 H130 0.9500 . ?
C130 C131 1.3900 . ?
C131 H131 0.9500 . ?
C131 C132 1.3900 . ?
C132 H132 0.9500 . ?
C132 C133 1.3900 . ?
C133 H133 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
C10 Au1 Br1 174.6(4) . . ?
C110 Au2 Br2 174.7(4) . . ?
C105 C104 H104 119.4 . . ?
C103 C104 H104 119.2 . . ?
C103 C104 C105 121.4(14) . . ?
N7 N8 C18 118.7(11) . . ?
C10 N8 N7 113.8(11) . . ?
C10 N8 C18 127.5(12) . . ?
C101 C102 C107 121.3(12) . . ?
C103 C102 C101 116.1(13) . . ?
C103 C102 C107 122.5(13) . . ?
C11 N6 C1 128.7(12) . . ?
C11 N6 C10 107.1(11) . . ?
C10 N6 C1 123.4(12) . . ?
N3 N4 C118 118.9(11) . . ?
C110 N4 N3 112.9(11) . . ?
C110 N4 C118 128.1(12) . . ?
C111 N2 C101 126.6(12) . . ?
C110 N2 C111 107.7(11) . . ?
C110 N2 C101 125.4(12) . . ?
C111 N3 N4 105.2(12) . . ?
N4 C118 C121 114.9(13) . . ?
N4 C118 C119 105.3(15) . . ?
N4 C118 C120 104.9(14) . . ?
N4 C118 C202 109(2) . . ?
N4 C118 C200 103.7(15) . . ?
N4 C118 C201 114.4(19) . . ?
C121 C118 C119 112.5(13) . . ?
C121 C118 C120 109.6(12) . . ?
C119 C118 C120 109.2(13) . . ?
C202 C118 C200 109.6(15) . . ?
C201 C118 C202 109.8(15) . . ?
C201 C118 C200 110.5(15) . . ?
N2 C111 C112 127.6(13) . . ?
N3 C111 N2 109.8(13) . . ?
N3 C111 C112 122.6(13) . . ?
C11 N7 N8 104.2(12) . . ?
C8 N5 C9 109.2(14) . . ?
C7 N5 C8 110.9(13) . . ?
C7 N5 C9 110.7(13) . . ?
C1 C2 C7 121.5(13) . . ?
C3 C2 C1 117.8(14) . . ?
C3 C2 C7 120.7(13) . . ?
N4 C110 Au2 131.4(10) . . ?
N4 C110 N2 104.4(12) . . ?
N2 C110 Au2 124.0(10) . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C1 119.3(14) . . ?
C1 C6 H6 120.2 . . ?
C104 C105 H105 120.1 . . ?
C104 C105 C106 119.1(14) . . ?
C106 C105 H105 120.8 . . ?
H10A C108 H10B 109.5 . . ?
H10A C108 H10C 109.5 . . ?
H10B C108 H10C 109.5 . . ?
N1 C108 H10A 108.0 . . ?
N1 C108 H10B 109.6 . . ?
N1 C108 H10C 110.8 . . ?
C13 C12 C11 123.5(14) . . ?
C13 C12 C17 119.1(15) . . ?
C17 C12 C11 117.3(13) . . ?
N6 C11 C12 126.2(13) . . ?
N7 C11 N6 110.7(12) . . ?
N7 C11 C12 123.0(13) . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.3(17) . . ?
C14 C13 H13 119.2 . . ?
C117 C112 C111 119.0(13) . . ?
C117 C112 C113 119.4(15) . . ?
C113 C112 C111 121.5(14) . . ?
C105 C106 H106 120.4 . . ?
C101 C106 C105 119.0(13) . . ?
C101 C106 H106 120.6 . . ?
C108 N1 C109 113.3(14) . . ?
C108 N1 C107 112.2(13) . . ?
C107 N1 C109 110.0(13) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.3(15) . . ?
C4 C5 H5 120.0 . . ?
C113 C114 H114 119.6 . . ?
C115 C114 H114 119.9 . . ?
C115 C114 C113 120.5(15) . . ?
N5 C8 H8A 109.2 . . ?
N5 C8 H8B 108.8 . . ?
N5 C8 H8C 110.4 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.6(14) . . ?
C3 C4 H4 120.2 . . ?
C102 C101 N2 118.2(12) . . ?
C106 C101 C102 122.6(13) . . ?
C106 C101 N2 119.1(12) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 120.5(17) . . ?
C15 C14 H14 118.8 . . ?
C2 C1 N6 120.5(13) . . ?
C2 C1 C6 121.3(13) . . ?
C6 C1 N6 118.2(12) . . ?
C14 C15 H15 121.3 . . ?
C14 C15 C16 118.4(16) . . ?
C16 C15 H15 120.3 . . ?
C112 C117 H117 119.5 . . ?
C116 C117 C112 121.7(15) . . ?
C116 C117 H117 118.8 . . ?
C112 C113 C114 118.9(15) . . ?
C112 C113 H113 120.2 . . ?
C114 C113 H113 120.9 . . ?
N8 C18 C19 107.1(12) . . ?
C21 C18 N8 108.3(12) . . ?
C21 C18 C19 112.1(15) . . ?
C20 C18 N8 107.6(13) . . ?
C20 C18 C21 110.3(15) . . ?
C20 C18 C19 111.2(17) . . ?
N5 C7 C2 112.9(13) . . ?
N5 C7 H7A 108.7 . . ?
N5 C7 H7B 109.4 . . ?
C2 C7 H7A 108.5 . . ?
C2 C7 H7B 109.6 . . ?
H7A C7 H7B 107.7 . . ?
C117 C116 H116 120.5 . . ?
C117 C116 C115 119.5(16) . . ?
C115 C116 H116 119.9 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 120.5(15) . . ?
C16 C17 H17 119.4 . . ?
C114 C115 C116 119.9(17) . . ?
C114 C115 H115 120.1 . . ?
C116 C115 H115 120.0 . . ?
C104 C103 C102 121.8(13) . . ?
C104 C103 H103 118.9 . . ?
C102 C103 H103 119.3 . . ?
N1 C109 H10D 109.4 . . ?
N1 C109 H10E 109.9 . . ?
N1 C109 H10F 109.1 . . ?
H10D C109 H10E 109.5 . . ?
H10D C109 H10F 109.5 . . ?
H10E C109 H10F 109.5 . . ?
C102 C107 H10G 108.8 . . ?
C102 C107 H10H 109.2 . . ?
N1 C107 C102 113.0(12) . . ?
N1 C107 H10G 109.0 . . ?
N1 C107 H10H 108.8 . . ?
H10G C107 H10H 107.9 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.1(17) . . ?
C17 C16 H16 120.2 . . ?
C2 C3 C4 121.8(14) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 118.7 . . ?
N5 C9 H9A 108.9 . . ?
N5 C9 H9B 109.8 . . ?
N5 C9 H9C 109.7 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N8 C10 Au1 130.8(10) . . ?
N8 C10 N6 104.1(12) . . ?
N6 C10 Au1 125.1(10) . . ?
C18 C21 H21A 109.3 . . ?
C18 C21 H21B 109.3 . . ?
C18 C21 H21C 109.8 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.4 . . ?
H21B C21 H21C 109.5 . . ?
C18 C19 H19A 110.5 . . ?
C18 C19 H19B 109.8 . . ?
C18 C19 H19C 108.1 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20J 107.8 . . ?
C18 C20 H20K 110.8 . . ?
C18 C20 H20L 109.8 . . ?
H20J C20 H20K 109.5 . . ?
H20J C20 H20L 109.4 . . ?
H20K C20 H20L 109.5 . . ?
C118 C121 H12A 109.5 . . ?
C118 C121 H12B 109.5 . . ?
C118 C121 H12C 109.5 . . ?
H12A C121 H12B 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
C118 C119 H11A 109.5 . . ?
C118 C119 H11B 109.5 . . ?
C118 C119 H11C 109.5 . . ?
H11A C119 H11B 109.5 . . ?
H11A C119 H11C 109.5 . . ?
H11B C119 H11C 109.5 . . ?
C118 C120 H12D 109.5 . . ?
C118 C120 H12E 109.5 . . ?
C118 C120 H12F 109.5 . . ?
H12D C120 H12E 109.5 . . ?
H12D C120 H12F 109.5 . . ?
H12E C120 H12F 109.5 . . ?
C118 C202 H20A 109.5 . . ?
C118 C202 H20B 109.5 . . ?
C118 C202 H20C 109.5 . . ?
H20A C202 H20B 109.5 . . ?
H20A C202 H20C 109.5 . . ?
H20B C202 H20C 109.5 . . ?
C118 C200 H20D 109.5 . . ?
C118 C200 H20E 109.5 . . ?
C118 C200 H20F 109.5 . . ?
H20D C200 H20E 109.5 . . ?
H20D C200 H20F 109.5 . . ?
H20E C200 H20F 109.5 . . ?
C118 C201 H20G 109.5 . . ?
C118 C201 H20H 109.5 . . ?
C118 C201 H20I 109.5 . . ?
H20G C201 H20H 109.5 . . ?
H20G C201 H20I 109.5 . . ?
H20H C201 H20I 109.5 . . ?
C23 C22 H22 120.0 . . ?
C23 C22 C27 120.0 . . ?
C27 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C22 C27 H27 120.0 . . ?
C26 C27 C22 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 H28 120.0 . . ?
C29 C28 C33 120.0 . . ?
C33 C28 H28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C28 C33 H33 120.0 . . ?
C32 C33 C28 120.0 . . ?
C32 C33 H33 120.0 . . ?
C129 C128 H128 120.0 . . ?
C129 C128 C133 120.0 . . ?
C133 C128 H128 120.0 . . ?
C128 C129 H129 120.0 . . ?
C130 C129 C128 120.0 . . ?
C130 C129 H129 120.0 . . ?
C129 C130 H130 120.0 . . ?
C129 C130 C131 120.0 . . ?
C131 C130 H130 120.0 . . ?
C130 C131 H131 120.0 . . ?
C132 C131 C130 120.0 . . ?
C132 C131 H131 120.0 . . ?
C131 C132 H132 120.0 . . ?
C133 C132 C131 120.0 . . ?
C133 C132 H132 120.0 . . ?
C128 C133 H133 120.0 . . ?
C132 C133 C128 120.0 . . ?
C132 C133 H133 120.0 . . ?

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
C104 C105 C106 C101 2(2) . . . . ?
N8 N7 C11 N6 -0.6(15) . . . . ?
N8 N7 C11 C12 179.2(13) . . . . ?
N4 N3 C111 N2 1.0(16) . . . . ?
N4 N3 C111 C112 178.4(13) . . . . ?
N2 C111 C112 C117 150.8(15) . . . . ?
N2 C111 C112 C113 -33(2) . . . . ?
N3 N4 C118 C121 -157.3(14) . . . . ?
N3 N4 C118 C119 78.4(17) . . . . ?
N3 N4 C118 C120 -36.8(17) . . . . ?
N3 N4 C118 C202 -128.3(19) . . . . ?
N3 N4 C118 C200 115.2(18) . . . . ?
N3 N4 C118 C201 -5(2) . . . . ?
N3 N4 C110 Au2 -173.7(10) . . . . ?
N3 N4 C110 N2 1.0(15) . . . . ?
N3 C111 C112 C117 -26(2) . . . . ?
N3 C111 C112 C113 150.5(15) . . . . ?
C118 N4 N3 C111 -177.6(12) . . . . ?
C118 N4 C110 Au2 2(2) . . . . ?
C118 N4 C110 N2 177.0(12) . . . . ?
C111 N2 C110 Au2 174.9(9) . . . . ?
C111 N2 C110 N4 -0.4(14) . . . . ?
C111 N2 C101 C102 -69.8(18) . . . . ?
C111 N2 C101 C106 107.3(16) . . . . ?
C111 C112 C117 C116 178.1(16) . . . . ?
C111 C112 C113 C114 -175.4(15) . . . . ?
N7 N8 C18 C21 -10.0(18) . . . . ?
N7 N8 C18 C19 111.0(16) . . . . ?
N7 N8 C18 C20 -129.3(15) . . . . ?
N7 N8 C10 Au1 178.9(10) . . . . ?
N7 N8 C10 N6 -1.3(15) . . . . ?
C110 N4 N3 C111 -1.3(16) . . . . ?
C110 N4 C118 C121 27(2) . . . . ?
C110 N4 C118 C119 -97.4(18) . . . . ?
C110 N4 C118 C120 147.4(16) . . . . ?
C110 N4 C118 C202 56(2) . . . . ?
C110 N4 C118 C200 -61(2) . . . . ?
C110 N4 C118 C201 179(2) . . . . ?
C110 N2 C111 N3 -0.4(16) . . . . ?
C110 N2 C111 C112 -177.7(13) . . . . ?
C110 N2 C101 C102 104.1(15) . . . . ?
C110 N2 C101 C106 -78.8(17) . . . . ?
C6 C5 C4 C3 1(2) . . . . ?
C105 C104 C103 C102 3(2) . . . . ?
C105 C106 C101 C102 0(2) . . . . ?
C105 C106 C101 N2 -177.2(12) . . . . ?
C108 N1 C107 C102 -64.5(17) . . . . ?
C12 C13 C14 C15 -1(3) . . . . ?
C12 C17 C16 C15 2(3) . . . . ?
C11 N6 C1 C2 67(2) . . . . ?
C11 N6 C1 C6 -111.9(17) . . . . ?
C11 N6 C10 Au1 -179.3(10) . . . . ?
C11 N6 C10 N8 0.9(14) . . . . ?
C11 C12 C13 C14 175.7(15) . . . . ?
C11 C12 C17 C16 -176.5(15) . . . . ?
C13 C12 C11 N6 32(2) . . . . ?
C13 C12 C11 N7 -147.7(16) . . . . ?
C13 C12 C17 C16 -1(2) . . . . ?
C13 C14 C15 C16 2(3) . . . . ?
C112 C117 C116 C115 -3(3) . . . . ?
C5 C6 C1 N6 178.5(13) . . . . ?
C5 C6 C1 C2 0(2) . . . . ?
C5 C4 C3 C2 0(2) . . . . ?
C8 N5 C7 C2 -172.2(14) . . . . ?
C101 C102 C103 C104 -1(2) . . . . ?
C101 C102 C107 N1 -57.1(19) . . . . ?
C101 N2 C111 N3 174.4(13) . . . . ?
C101 N2 C111 C112 -3(2) . . . . ?
C101 N2 C110 Au2 0.0(18) . . . . ?
C101 N2 C110 N4 -175.2(12) . . . . ?
C14 C15 C16 C17 -2(3) . . . . ?
C1 N6 C11 N7 -170.5(13) . . . . ?
C1 N6 C11 C12 10(2) . . . . ?
C1 N6 C10 Au1 -8.4(18) . . . . ?
C1 N6 C10 N8 171.8(12) . . . . ?
C1 C2 C7 N5 55.7(19) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C1 C6 C5 C4 0(2) . . . . ?
C117 C112 C113 C114 1(2) . . . . ?
C117 C116 C115 C114 2(3) . . . . ?
C113 C112 C117 C116 1(3) . . . . ?
C113 C114 C115 C116 0(3) . . . . ?
C18 N8 N7 C11 -179.6(12) . . . . ?
C18 N8 C10 Au1 0(2) . . . . ?
C18 N8 C10 N6 179.6(12) . . . . ?
C7 C2 C1 N6 4(2) . . . . ?
C7 C2 C1 C6 -177.0(13) . . . . ?
C7 C2 C3 C4 177.4(14) . . . . ?
C17 C12 C11 N6 -152.7(15) . . . . ?
C17 C12 C11 N7 28(2) . . . . ?
C17 C12 C13 C14 0(2) . . . . ?
C115 C114 C113 C112 -2(3) . . . . ?
C103 C104 C105 C106 -3(2) . . . . ?
C103 C102 C101 N2 176.9(12) . . . . ?
C103 C102 C101 C106 0(2) . . . . ?
C103 C102 C107 N1 121.8(15) . . . . ?
C109 N1 C107 C102 168.4(14) . . . . ?
C107 C102 C101 N2 -4(2) . . . . ?
C107 C102 C101 C106 178.8(13) . . . . ?
C107 C102 C103 C104 179.9(14) . . . . ?
C3 C2 C1 N6 -178.3(13) . . . . ?
C3 C2 C1 C6 0(2) . . . . ?
C3 C2 C7 N5 -121.6(15) . . . . ?
C9 N5 C7 C2 66.5(17) . . . . ?
C10 N8 N7 C11 1.2(15) . . . . ?
C10 N8 C18 C21 169.1(14) . . . . ?
C10 N8 C18 C19 -69.8(19) . . . . ?
C10 N8 C18 C20 50(2) . . . . ?
C10 N6 C11 N7 -0.2(16) . . . . ?
C10 N6 C11 C12 -179.9(13) . . . . ?
C10 N6 C1 C2 -102.1(17) . . . . ?
C10 N6 C1 C6 79.2(17) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C22 C27 C26 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C22 0.0 . . . . ?
C27 C22 C23 C24 0.0 . . . . ?
C28 C29 C30 C31 0.0 . . . . ?
C29 C28 C33 C32 0.0 . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C30 C31 C32 C33 0.0 . . . . ?
C31 C32 C33 C28 0.0 . . . . ?
C33 C28 C29 C30 0.0 . . . . ?
C128 C129 C130 C131 0.0 . . . . ?
C129 C128 C133 C132 0.0 . . . . ?
C129 C130 C131 C132 0.0 . . . . ?
C130 C131 C132 C133 0.0 . . . . ?
C131 C132 C133 C128 0.0 . . . . ?
C133 C128 C129 C130 0.0 . . . . ?



_database_code_depnum_ccdc_archive 'CCDC 1011245'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 Au I N4, 0.5(C6 H6)'
_chemical_formula_sum            'C24 H29 Au I N4'
_chemical_formula_weight         697.38

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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   13.5419(10)
_cell_length_b                   14.5710(5)
_cell_length_c                   14.1930(8)
_cell_angle_alpha                90
_cell_angle_beta                 119.557(5)
_cell_angle_gamma                90
_cell_volume                     2436.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    20611
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1332
_exptl_absorpt_coefficient_mu    7.324
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 1 0.023
0 1 -1 0.115
0 -1 -1 0.086
0 1 1 0.121
-1 0 1 0.017
1 0 -1 0.055


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.209
_exptl_absorpt_correction_T_max  0.623
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20514
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5559
_reflns_number_gt                4762
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0425P)²+32.6153P] 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         5559
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.45375(2) 0.581294(19) 0.55584(2) 0.01983(9) Uani 1 1 d . . .
I1 I 0.63590(4) 0.66156(4) 0.69449(4) 0.02936(13) Uani 1 1 d . . .
C2 C 0.2429(6) 0.7289(5) 0.3313(5) 0.0196(14) Uani 1 1 d . . .
C10 C 0.3008(6) 0.5268(4) 0.4523(5) 0.0160(13) Uani 1 1 d . . .
C14 C -0.1842(6) 0.5337(6) 0.1179(6) 0.0272(16) Uani 1 1 d . . .
H14 H -0.2518 0.5216 0.1176 0.033 Uiso 1 1 d R . .
C7 C 0.1983(6) 0.7475(5) 0.4083(6) 0.0215(14) Uani 1 1 d . . .
H7A H 0.2484 0.7189 0.4774 0.026 Uiso 1 1 d R . .
H7B H 0.1985 0.8131 0.4201 0.026 Uiso 1 1 d R . .
C6 C 0.3042(6) 0.6197(5) 0.2408(6) 0.0222(14) Uani 1 1 d . . .
H6 H 0.3131 0.5593 0.2251 0.027 Uiso 1 1 d R . .
C19 C 0.2297(8) 0.4414(6) 0.6300(6) 0.0309(17) Uani 1 1 d . . .
H19A H 0.1493 0.4514 0.5876 0.037 Uiso 1 1 d R . .
H19B H 0.2674 0.4991 0.6572 0.037 Uiso 1 1 d R . .
H19C H 0.2453 0.4016 0.6896 0.037 Uiso 1 1 d R . .
N3 N 0.1318(5) 0.4557(4) 0.3808(4) 0.0175(11) Uani 1 1 d . . .
C9 C 0.0003(8) 0.7663(6) 0.2788(8) 0.039(2) Uani 1 1 d . . .
H9A H -0.0032 0.8272 0.3030 0.047 Uiso 1 1 d R . .
H9B H -0.0723 0.7372 0.2512 0.047 Uiso 1 1 d R . .
H9C H 0.0202 0.7696 0.2227 0.047 Uiso 1 1 d R . .
C1 C 0.2586(6) 0.6391(5) 0.3071(5) 0.0167(13) Uani 1 1 d . . .
C12 C 0.0200(6) 0.5377(4) 0.2119(5) 0.0163(13) Uani 1 1 d . . .
N1 N 0.0845(5) 0.7115(4) 0.3679(5) 0.0221(12) Uani 1 1 d . . .
C11 C 0.1257(6) 0.5186(4) 0.3125(5) 0.0164(13) Uani 1 1 d . . .
C20 C 0.3994(6) 0.3824(6) 0.6231(6) 0.0293(17) Uani 1 1 d . . .
H20A H 0.4164 0.3334 0.6740 0.035 Uiso 1 1 d R . .
H20B H 0.4362 0.4376 0.6612 0.035 Uiso 1 1 d R . .
H20C H 0.4261 0.3666 0.5739 0.035 Uiso 1 1 d R . .
N2 N 0.2285(5) 0.5636(4) 0.3536(4) 0.0138(10) Uani 1 1 d . . .
C17 C 0.0164(6) 0.5691(5) 0.1176(5) 0.0211(14) Uani 1 1 d . . .
H17 H 0.0835 0.5807 0.1169 0.025 Uiso 1 1 d R . .
C13 C -0.0817(6) 0.5199(5) 0.2106(6) 0.0237(15) Uani 1 1 d . . .
H13 H -0.0800 0.4985 0.2731 0.028 Uiso 1 1 d R . .
C15 C -0.1875(6) 0.5652(5) 0.0244(6) 0.0262(16) Uani 1 1 d . . .
H15 H -0.2569 0.5745 -0.0380 0.031 Uiso 1 1 d R . .
C4 C 0.3211(7) 0.7802(6) 0.2213(6) 0.0283(17) Uani 1 1 d . . .
H4 H 0.3435 0.8288 0.1936 0.034 Uiso 1 1 d R . .
N4 N 0.2419(5) 0.4618(4) 0.4662(4) 0.0165(11) Uani 1 1 d . . .
C21 C 0.2132(7) 0.3071(5) 0.5132(6) 0.0287(17) Uani 1 1 d . . .
H21A H 0.1337 0.3172 0.4652 0.034 Uiso 1 1 d R . .
H21B H 0.2229 0.2669 0.5707 0.034 Uiso 1 1 d R . .
H21C H 0.2462 0.2795 0.4737 0.034 Uiso 1 1 d R . .
C18 C 0.2716(6) 0.3973(5) 0.5594(5) 0.0172(13) Uani 1 1 d . . .
C3 C 0.2756(7) 0.7993(5) 0.2863(6) 0.0264(16) Uani 1 1 d . . .
H3 H 0.2662 0.8600 0.3005 0.032 Uiso 1 1 d R . .
C16 C -0.0880(7) 0.5832(6) 0.0246(6) 0.0273(16) Uani 1 1 d . . .
H16 H -0.0909 0.6044 -0.0385 0.033 Uiso 1 1 d R . .
C5 C 0.3354(6) 0.6920(6) 0.1977(6) 0.0242(15) Uani 1 1 d . . .
H5 H 0.3654 0.6806 0.1523 0.029 Uiso 1 1 d R . .
C8 C 0.0584(8) 0.7056(8) 0.4555(8) 0.043(2) Uani 1 1 d . . .
H8A H 0.0776 0.7620 0.4957 0.051 Uiso 1 1 d R . .
H8B H 0.1023 0.6564 0.5024 0.051 Uiso 1 1 d R . .
H8C H -0.0209 0.6931 0.4267 0.051 Uiso 1 1 d R . .
C24 C 0.5124(8) -0.0701(8) 0.5690(9) 0.051(3) Uani 1 1 d . . .
H24 H 0.5208 -0.1170 0.6168 0.062 Uiso 1 1 d R . .
C22 C 0.4825(8) 0.0877(8) 0.5212(9) 0.053(3) Uani 1 1 d . . .
H22 H 0.4686 0.1476 0.5341 0.064 Uiso 1 1 d R . .
C23 C 0.4937(8) 0.0173(10) 0.5918(8) 0.054(3) Uani 1 1 d . . .
H23 H 0.4911 0.0309 0.6546 0.065 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C10 2.020(7) . ?
Au1 I1 2.5565(6) . ?
C2 C3 1.391(10) . ?
C2 C1 1.396(10) . ?
C2 C7 1.510(10) . ?
C10 N4 1.314(9) . ?
C10 N2 1.363(8) . ?
C14 C13 1.378(10) . ?
C14 C15 1.384(11) . ?
C14 H14 0.9301 . ?
C7 N1 1.452(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 C1 1.384(10) . ?
C6 C5 1.385(11) . ?
C6 H6 0.9300 . ?
C19 C18 1.517(11) . ?
C19 H19A 0.9601 . ?
C19 H19B 0.9599 . ?
C19 H19C 0.9599 . ?
N3 C11 1.305(9) . ?
N3 N4 1.385(8) . ?
C9 N1 1.454(10) . ?
C9 H9A 0.9601 . ?
C9 H9B 0.9599 . ?
C9 H9C 0.9600 . ?
C1 N2 1.441(8) . ?
C12 C17 1.391(9) . ?
C12 C13 1.393(10) . ?
C12 C11 1.466(9) . ?
N1 C8 1.453(10) . ?
C11 N2 1.382(8) . ?
C20 C18 1.522(10) . ?
C20 H20A 0.9601 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9599 . ?
C17 C16 1.393(10) . ?
C17 H17 0.9299 . ?
C13 H13 0.9299 . ?
C15 C16 1.370(12) . ?
C15 H15 0.9299 . ?
C4 C5 1.366(12) . ?
C4 C3 1.368(12) . ?
C4 H4 0.9300 . ?
N4 C18 1.505(8) . ?
C21 C18 1.508(10) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C3 H3 0.9300 . ?
C16 H16 0.9300 . ?
C5 H5 0.9299 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9599 . ?
C8 H8C 0.9599 . ?
C24 C22 1.340(17) 3_656 ?
C24 C23 1.368(18) . ?
C24 H24 0.9303 . ?
C22 C24 1.340(17) 3_656 ?
C22 C23 1.388(17) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 Au1 I1 173.69(19) . . ?
C3 C2 C1 117.1(7) . . ?
C3 C2 C7 122.0(7) . . ?
C1 C2 C7 120.7(6) . . ?
N4 C10 N2 104.9(6) . . ?
N4 C10 Au1 130.9(5) . . ?
N2 C10 Au1 123.5(5) . . ?
C13 C14 C15 120.4(7) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 119.5 . . ?
N1 C7 C2 112.0(6) . . ?
N1 C7 H7A 108.6 . . ?
C2 C7 H7A 109.0 . . ?
N1 C7 H7B 109.6 . . ?
C2 C7 H7B 109.6 . . ?
H7A C7 H7B 108.0 . . ?
C1 C6 C5 118.7(7) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C18 C19 H19A 109.2 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.6 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 N3 N4 104.6(5) . . ?
N1 C9 H9A 110.6 . . ?
N1 C9 H9B 108.6 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.2 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C1 C2 122.1(6) . . ?
C6 C1 N2 118.5(6) . . ?
C2 C1 N2 119.4(6) . . ?
C17 C12 C13 118.9(6) . . ?
C17 C12 C11 123.6(6) . . ?
C13 C12 C11 117.4(6) . . ?
C7 N1 C8 110.1(6) . . ?
C7 N1 C9 111.6(6) . . ?
C8 N1 C9 111.1(7) . . ?
N3 C11 N2 109.8(6) . . ?
N3 C11 C12 122.1(6) . . ?
N2 C11 C12 128.1(6) . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.7 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.2 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 N2 C11 108.0(5) . . ?
C10 N2 C1 123.4(5) . . ?
C11 N2 C1 128.6(5) . . ?
C12 C17 C16 119.8(7) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 120.3 . . ?
C14 C13 C12 120.6(7) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 119.5 . . ?
C16 C15 C14 119.6(7) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.0 . . ?
C5 C4 C3 121.5(7) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 118.7 . . ?
C10 N4 N3 112.6(5) . . ?
C10 N4 C18 131.5(6) . . ?
N3 N4 C18 115.8(5) . . ?
C18 C21 H21A 109.7 . . ?
C18 C21 H21B 109.9 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 108.8 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C18 C21 107.9(5) . . ?
N4 C18 C19 106.9(6) . . ?
C21 C18 C19 111.7(6) . . ?
N4 C18 C20 110.1(6) . . ?
C21 C18 C20 109.4(7) . . ?
C19 C18 C20 110.8(6) . . ?
C4 C3 C2 120.8(7) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.6 . . ?
C15 C16 C17 120.7(7) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 120.1 . . ?
C4 C5 C6 119.8(7) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N1 C8 H8A 110.5 . . ?
N1 C8 H8B 108.0 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.9 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C22 C24 C23 120.5(10) 3_656 . ?
C22 C24 H24 120.7 3_656 . ?
C23 C24 H24 118.8 . . ?
C24 C22 C23 120.5(11) 3_656 . ?
C24 C22 H22 118.6 3_656 . ?
C23 C22 H22 120.9 . . ?
C24 C23 C22 119.0(10) . . ?
C24 C23 H23 121.5 . . ?
C22 C23 H23 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         6.428
_refine_diff_density_min         -2.278
_refine_diff_density_rms         0.229
_database_code_depnum_ccdc_archive 'CCDC 1011246'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 Ag Cl N3'
_chemical_formula_sum            'C19 H21 Ag Cl N3'
_chemical_formula_weight         434.71

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'
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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.9450(3)
_cell_length_b                   10.9861(7)
_cell_length_c                   10.9950(6)
_cell_angle_alpha                62.599(4)
_cell_angle_beta                 72.338(3)
_cell_angle_gamma                80.124(3)
_cell_volume                     913.39(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    19102
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    1.254
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.073
0 0 1 0.152
1 0 0 0.134
-1 0 0 0.138
0 1 0 0.082
0 -1 0 0.129
1 0 1 0.166
0 1 1 0.161
0 -1 -1 0.139


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19018
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4169
_reflns_number_gt                3963
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0514P)²+1.8563P] 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         4169
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.67826(2) 0.47162(2) -0.10890(2) 0.02128(9) Uani 1 1 d . . .
Cl1 Cl 0.81674(7) 0.66844(6) -0.28513(6) 0.01592(13) Uani 1 1 d . . .
N3 N 0.5933(3) 0.1950(2) 0.1686(2) 0.0168(4) Uani 1 1 d . . .
N2 N 0.4945(3) 0.0869(2) 0.2342(2) 0.0189(4) Uani 1 1 d . . .
C8 C 0.4827(3) 0.3037(3) -0.2243(3) 0.0196(5) Uani 1 1 d . . .
H8 H 0.5861 0.2697 -0.2345 0.023 Uiso 1 1 d R . .
N1 N 0.4577(3) 0.2340(2) 0.0259(2) 0.0158(4) Uani 1 1 d . . .
C6 C 0.2606(3) 0.4110(3) -0.3244(3) 0.0194(5) Uani 1 1 d . . .
C2 C 0.4123(3) 0.1135(3) 0.1440(3) 0.0169(5) Uani 1 1 d . . .
C1 C 0.5737(3) 0.2879(3) 0.0418(3) 0.0181(5) Uani 1 1 d . . .
C7 C 0.4157(3) 0.3595(3) -0.3379(3) 0.0215(5) Uani 1 1 d . . .
H7 H 0.4754 0.3633 -0.4250 0.026 Uiso 1 1 d R . .
C11 C 0.2086(3) -0.0521(3) 0.3102(3) 0.0240(6) Uani 1 1 d . . .
H11 H 0.2252 -0.0388 0.3827 0.029 Uiso 1 1 d R . .
C4 C 0.2381(3) 0.3482(3) -0.0775(3) 0.0178(5) Uani 1 1 d . . .
H4 H 0.1785 0.3431 0.0101 0.021 Uiso 1 1 d R . .
C10 C 0.2920(3) 0.0223(3) 0.1706(3) 0.0178(5) Uani 1 1 d . . .
C16 C 0.6975(3) 0.1986(3) 0.2510(3) 0.0201(5) Uani 1 1 d . . .
C3 C 0.3921(3) 0.2986(3) -0.0949(3) 0.0153(5) Uani 1 1 d . . .
C14 C 0.1517(4) -0.0880(3) 0.0954(4) 0.0270(6) Uani 1 1 d . . .
H14 H 0.1317 -0.1002 0.0236 0.032 Uiso 1 1 d R . .
C18 C 0.7398(4) 0.0508(3) 0.3454(4) 0.0310(7) Uani 1 1 d . . .
H18A H 0.6511 0.0106 0.4237 0.037 Uiso 1 1 d R . .
H18B H 0.8260 0.0503 0.3805 0.037 Uiso 1 1 d R . .
H18C H 0.7696 -0.0014 0.2911 0.037 Uiso 1 1 d R . .
C9 C 0.1896(4) 0.4738(4) -0.4493(3) 0.0299(6) Uani 1 1 d . . .
H9A H 0.0784 0.4877 -0.4177 0.036 Uiso 1 1 d R . .
H9B H 0.2097 0.4131 -0.4939 0.036 Uiso 1 1 d R . .
H9C H 0.2359 0.5602 -0.5162 0.036 Uiso 1 1 d R . .
C15 C 0.2629(3) 0.0046(3) 0.0618(3) 0.0218(5) Uani 1 1 d . . .
H15 H 0.3170 0.0542 -0.0320 0.026 Uiso 1 1 d R . .
C5 C 0.1730(3) 0.4051(3) -0.1935(3) 0.0210(5) Uani 1 1 d . . .
H5 H 0.0701 0.4403 -0.1836 0.025 Uiso 1 1 d R . .
C12 C 0.0991(4) -0.1448(3) 0.3419(4) 0.0309(7) Uani 1 1 d . . .
H12 H 0.0454 -0.1957 0.4355 0.037 Uiso 1 1 d R . .
C19 C 0.8466(4) 0.2728(4) 0.1502(4) 0.0324(7) Uani 1 1 d . . .
H19A H 0.9086 0.2192 0.1027 0.039 Uiso 1 1 d R . .
H19B H 0.9060 0.2857 0.2026 0.039 Uiso 1 1 d R . .
H19C H 0.8190 0.3605 0.0813 0.039 Uiso 1 1 d R . .
C17 C 0.6058(4) 0.2732(4) 0.3402(4) 0.0287(6) Uani 1 1 d . . .
H17A H 0.5777 0.3649 0.2790 0.034 Uiso 1 1 d R . .
H17B H 0.6699 0.2766 0.3944 0.034 Uiso 1 1 d R . .
H17C H 0.5123 0.2251 0.4032 0.034 Uiso 1 1 d R . .
C13 C 0.0709(4) -0.1624(3) 0.2345(4) 0.0317(7) Uani 1 1 d . . .
H13 H -0.0026 -0.2245 0.2558 0.038 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 C1 2.079(3) . ?
Ag1 Cl1 2.3601(6) . ?
N3 C1 1.340(4) . ?
N3 N2 1.377(3) . ?
N3 C16 1.499(3) . ?
N2 C2 1.308(3) . ?
C8 C7 1.386(4) . ?
C8 C3 1.387(4) . ?
C8 H8 0.9301 . ?
N1 C1 1.369(3) . ?
N1 C2 1.373(3) . ?
N1 C3 1.441(3) . ?
C6 C5 1.392(4) . ?
C6 C7 1.396(4) . ?
C6 C9 1.507(4) . ?
C2 C10 1.469(4) . ?
C7 H7 0.9300 . ?
C11 C12 1.388(4) . ?
C11 C10 1.393(4) . ?
C11 H11 0.9300 . ?
C4 C3 1.382(4) . ?
C4 C5 1.396(4) . ?
C4 H4 0.9300 . ?
C10 C15 1.399(4) . ?
C16 C19 1.522(4) . ?
C16 C17 1.525(4) . ?
C16 C18 1.528(4) . ?
C14 C13 1.382(5) . ?
C14 C15 1.392(4) . ?
C14 H14 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9601 . ?
C18 H18C 0.9599 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C15 H15 0.9299 . ?
C5 H5 0.9301 . ?
C12 C13 1.380(5) . ?
C12 H12 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9599 . ?
C19 H19C 0.9601 . ?
C17 H17A 0.9599 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ag1 Cl1 174.92(7) . . ?
C1 N3 N2 113.8(2) . . ?
C1 N3 C16 129.1(2) . . ?
N2 N3 C16 116.9(2) . . ?
C2 N2 N3 104.0(2) . . ?
C7 C8 C3 118.7(2) . . ?
C7 C8 H8 120.5 . . ?
C3 C8 H8 120.8 . . ?
C1 N1 C2 109.3(2) . . ?
C1 N1 C3 124.2(2) . . ?
C2 N1 C3 126.5(2) . . ?
C5 C6 C7 118.7(2) . . ?
C5 C6 C9 120.4(3) . . ?
C7 C6 C9 120.9(3) . . ?
N2 C2 N1 110.1(2) . . ?
N2 C2 C10 122.6(2) . . ?
N1 C2 C10 127.2(2) . . ?
N3 C1 N1 102.7(2) . . ?
N3 C1 Ag1 133.9(2) . . ?
N1 C1 Ag1 123.45(19) . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.3 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.9 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.5 . . ?
C11 C10 C15 119.5(3) . . ?
C11 C10 C2 118.1(2) . . ?
C15 C10 C2 122.4(2) . . ?
N3 C16 C19 110.1(2) . . ?
N3 C16 C17 107.7(2) . . ?
C19 C16 C17 110.6(3) . . ?
N3 C16 C18 108.1(2) . . ?
C19 C16 C18 109.5(3) . . ?
C17 C16 C18 110.9(3) . . ?
C4 C3 C8 121.6(2) . . ?
C4 C3 N1 119.1(2) . . ?
C8 C3 N1 119.2(2) . . ?
C13 C14 C15 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.7 . . ?
C16 C18 H18A 109.8 . . ?
C16 C18 H18B 109.2 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.4 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C9 H9A 109.6 . . ?
C6 C9 H9B 109.3 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C14 C15 C10 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.7 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 120.1 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.6 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.3 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.6 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.844
_refine_diff_density_min         -0.860
_refine_diff_density_rms         0.106
_database_code_depnum_ccdc_archive 'CCDC 1011247'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 Au Cl N3'
_chemical_formula_sum            'C19 H21 Au Cl N3'
_chemical_formula_weight         523.80

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.9260(3)
_cell_length_b                   11.0071(6)
_cell_length_c                   11.0180(8)
_cell_angle_alpha                62.047(5)
_cell_angle_beta                 71.966(6)
_cell_angle_gamma                80.177(5)
_cell_volume                     908.82(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    19195
_cell_measurement_theta_min      1
_cell_measurement_theta_max      28.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    8.246
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.082
-1 0 0 0.060
0 1 1 0.059
0 -1 -1 0.078
0 0 1 0.071
0 0 -1 0.088
0 1 0 0.090
0 -1 0 0.079


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.301
_exptl_absorpt_correction_T_max  0.423
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19132
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         28.50
_reflns_number_total             4560
_reflns_number_gt                4364
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0313P)²+1.3216P] 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         4560
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0615
_refine_ls_wR_factor_gt          0.0597
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.683794(13) 0.463792(11) -0.108311(12) 0.01677(5) Uani 1 1 d . . .
Cl1 Cl 0.80694(10) 0.66389(8) -0.27857(9) 0.02175(16) Uani 1 1 d . . .
C3 C 0.3970(4) 0.3004(3) -0.0998(3) 0.0156(6) Uani 1 1 d . . .
N3 N 0.6000(3) 0.1953(3) 0.1639(3) 0.0166(5) Uani 1 1 d . . .
N2 N 0.4986(3) 0.0886(3) 0.2296(3) 0.0196(5) Uani 1 1 d . . .
C17 C 0.7358(5) 0.0491(4) 0.3471(4) 0.0294(8) Uani 1 1 d . . .
H17A H 0.6397 0.0092 0.4165 0.035 Uiso 1 1 d R . .
H17B H 0.8110 0.0465 0.3946 0.035 Uiso 1 1 d R . .
H17C H 0.7776 -0.0022 0.2928 0.035 Uiso 1 1 d R . .
C6 C 0.2610(4) 0.4105(3) -0.3264(4) 0.0198(6) Uani 1 1 d . . .
C19 C 0.8573(4) 0.2656(5) 0.1492(4) 0.0298(8) Uani 1 1 d . . .
H19A H 0.9089 0.2183 0.0923 0.036 Uiso 1 1 d R . .
H19B H 0.9238 0.2615 0.2048 0.036 Uiso 1 1 d R . .
H19C H 0.8366 0.3599 0.0881 0.036 Uiso 1 1 d R . .
C10 C 0.2934(4) 0.0247(3) 0.1688(4) 0.0179(6) Uani 1 1 d . . .
C1 C 0.5812(4) 0.2886(3) 0.0361(4) 0.0167(6) Uani 1 1 d . . .
C4 C 0.4857(4) 0.3038(3) -0.2294(3) 0.0184(6) Uani 1 1 d . . .
H4 H 0.5895 0.2704 -0.2407 0.022 Uiso 1 1 d R . .
C5 C 0.4162(4) 0.3584(3) -0.3413(4) 0.0207(6) Uani 1 1 d . . .
H5 H 0.4741 0.3603 -0.4283 0.025 Uiso 1 1 d R . .
C15 C 0.2103(4) -0.0498(4) 0.3098(4) 0.0242(7) Uani 1 1 d . . .
H15 H 0.2282 -0.0374 0.3820 0.029 Uiso 1 1 d R . .
C2 C 0.4155(4) 0.1153(3) 0.1406(3) 0.0173(6) Uani 1 1 d . . .
N1 N 0.4634(3) 0.2359(3) 0.0205(3) 0.0158(5) Uani 1 1 d . . .
C11 C 0.2634(4) 0.0072(3) 0.0608(4) 0.0213(7) Uani 1 1 d . . .
H11 H 0.3181 0.0569 -0.0337 0.026 Uiso 1 1 d R . .
C12 C 0.1507(5) -0.0858(4) 0.0963(5) 0.0265(7) Uani 1 1 d . . .
H12 H 0.1289 -0.0972 0.0251 0.032 Uiso 1 1 d R . .
C13 C 0.0708(5) -0.1605(4) 0.2363(5) 0.0318(9) Uani 1 1 d . . .
H13 H -0.0025 -0.2238 0.2593 0.038 Uiso 1 1 d R . .
C16 C 0.7024(4) 0.1976(3) 0.2476(3) 0.0183(6) Uani 1 1 d . . .
C8 C 0.2427(4) 0.3508(3) -0.0813(4) 0.0181(6) Uani 1 1 d . . .
H8 H 0.1851 0.3482 0.0061 0.022 Uiso 1 1 d R . .
C9 C 0.1880(5) 0.4715(4) -0.4493(4) 0.0297(8) Uani 1 1 d . . .
H9A H 0.0799 0.4971 -0.4178 0.036 Uiso 1 1 d R . .
H9B H 0.1929 0.4048 -0.4834 0.036 Uiso 1 1 d R . .
H9C H 0.2438 0.5516 -0.5247 0.036 Uiso 1 1 d R . .
C18 C 0.6110(5) 0.2767(4) 0.3322(4) 0.0275(7) Uani 1 1 d . . .
H18A H 0.5940 0.3705 0.2675 0.033 Uiso 1 1 d R . .
H18B H 0.6705 0.2741 0.3926 0.033 Uiso 1 1 d R . .
H18C H 0.5112 0.2351 0.3896 0.033 Uiso 1 1 d R . .
C7 C 0.1753(4) 0.4060(3) -0.1951(4) 0.0206(6) Uani 1 1 d . . .
H7 H 0.0716 0.4397 -0.1832 0.025 Uiso 1 1 d R . .
C14 C 0.0997(5) -0.1427(4) 0.3430(4) 0.0297(8) Uani 1 1 d . . .
H14 H 0.0440 -0.1926 0.4372 0.036 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 1.978(3) . ?
Au1 Cl1 2.2922(8) . ?
C3 C8 1.384(4) . ?
C3 C4 1.388(4) . ?
C3 N1 1.440(4) . ?
N3 C1 1.341(4) . ?
N3 N2 1.372(4) . ?
N3 C16 1.496(4) . ?
N2 C2 1.305(4) . ?
C17 C16 1.523(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9601 . ?
C17 H17C 0.9600 . ?
C6 C7 1.393(5) . ?
C6 C5 1.397(5) . ?
C6 C9 1.501(5) . ?
C19 C16 1.519(5) . ?
C19 H19A 0.9601 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C10 C15 1.391(5) . ?
C10 C11 1.398(5) . ?
C10 C2 1.466(4) . ?
C1 N1 1.373(4) . ?
C4 C5 1.385(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C15 C14 1.387(5) . ?
C15 H15 0.9300 . ?
C2 N1 1.375(4) . ?
C11 C12 1.395(5) . ?
C11 H11 0.9299 . ?
C12 C13 1.376(6) . ?
C12 H12 0.9299 . ?
C13 C14 1.381(6) . ?
C13 H13 0.9300 . ?
C16 C18 1.529(5) . ?
C8 C7 1.390(5) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9599 . ?
C18 H18C 0.9600 . ?
C7 H7 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Au1 Cl1 178.55(9) . . ?
C8 C3 C4 121.5(3) . . ?
C8 C3 N1 119.1(3) . . ?
C4 C3 N1 119.4(3) . . ?
C1 N3 N2 113.0(3) . . ?
C1 N3 C16 129.9(3) . . ?
N2 N3 C16 116.9(3) . . ?
C2 N2 N3 105.1(3) . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.4 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C6 C5 118.6(3) . . ?
C7 C6 C9 120.5(3) . . ?
C5 C6 C9 120.9(3) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.6 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.3 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C10 C11 119.9(3) . . ?
C15 C10 C2 117.7(3) . . ?
C11 C10 C2 122.4(3) . . ?
N3 C1 N1 103.3(3) . . ?
N3 C1 Au1 133.2(2) . . ?
N1 C1 Au1 123.5(2) . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.3 . . ?
C14 C15 C10 119.9(4) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 120.3 . . ?
N2 C2 N1 109.7(3) . . ?
N2 C2 C10 123.0(3) . . ?
N1 C2 C10 127.2(3) . . ?
C1 N1 C2 108.9(3) . . ?
C1 N1 C3 125.1(3) . . ?
C2 N1 C3 126.0(3) . . ?
C12 C11 C10 119.3(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.4 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.8 . . ?
N3 C16 C19 110.7(3) . . ?
N3 C16 C17 107.6(3) . . ?
C19 C16 C17 109.2(3) . . ?
N3 C16 C18 107.4(3) . . ?
C19 C16 C18 110.9(3) . . ?
C17 C16 C18 110.9(3) . . ?
C3 C8 C7 119.2(3) . . ?
C3 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C6 C9 H9A 109.1 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.8 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C16 C18 H18A 109.4 . . ?
C16 C18 H18B 109.4 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.7 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.483
_refine_diff_density_min         -2.222
_refine_diff_density_rms         0.158
_database_code_depnum_ccdc_archive 'CCDC 1011248'
#######################################################################
#
#                 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_jt130204cu1
# start Validation Reply Form
_vrf_PLAT601_jt130204cu1         
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        151 Ang3  
RESPONSE: No solvent molecule is localized in VOIDS. The model of solvent
molecule 

Although the structure is containing solvent accessible voids with 
the total volume of 151 \%A3, 
by using solvent masking technique (two methods) 
[P. v.d. Sluis & A.L. Spek, Acta Cryst. A46, (1990), 194] &
[B. Rees, L. Jenner & M. Yusupov, Acta Cryst. D61, (2005) 1299]
we revealed that these voids are empty (electron population 0.0). 
;
# end Validation Reply Form

_audit_creation_date             2014-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H21 Br0.5 Cl0.5 Cu N3, C4 H8 O'
_chemical_formula_sum            'C23 H29 Br0.50 Cl0.50 Cu N3 O'
_chemical_formula_weight         484.71
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3200 1.2650 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.2450(9)
_cell_length_b                   16.2720(14)
_cell_length_c                   17.9170(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 111.442(4)
_cell_angle_gamma                90.000(8)
_cell_volume                     2508.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.661
_shelx_estimated_absorpt_T_min   0.511
_exptl_absorpt_coefficient_mu    1.737
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.836878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0393 before and 0.0295 after correction.
The Ratio of minimum to maximum transmission is 0.8369.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.447
_exptl_crystal_size_mid          0.399
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23685
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         4.169
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4206
_reflns_number_total             5080
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5080
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+5.0058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1019
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 O1-C20 = O1-C23 = O2-C30 = O2-C33
 1.43 with sigma of 0.01
 C20-C21 = C21-C22 = C22-C23 = C30-C31 = C31-C32 = C32-C33
 1.54 with sigma of 0.01
 C20-C23 \\sim C30-C33
 with sigma of 0.02
 O1-C21 \\sim O1-C22 \\sim O2-C31 \\sim O2-C32
 with sigma of 0.02
 C20-C22 \\sim C21-C23 \\sim C30-C32 \\sim C31-C33
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O2)
Uanis(C20) = Uanis(C30)
Uanis(C21) = Uanis(C31)
Uanis(C22) = Uanis(C32)
Uanis(C23) = Uanis(C33)
Uanis(Br1) = Uanis(Cl1)
4. Others
 Sof(O2)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C33)=
 Sof(H33A)=Sof(H33B)=Sof(C32)=Sof(H32A)=Sof(H32B)=1-FVAR(1)
 Sof(O1)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C23)=
 Sof(H23A)=Sof(H23B)=Sof(C22)=Sof(H22A)=Sof(H22B)=FVAR(1)
 Fixed Sof: Br1(0.5) Cl1(0.5)
5.a Riding coordinates:
 C4(H4), C8(H8), C5(H5), C17(H17A,H17B,H17C), C13(H13), C11(H11), C15(H15),
 C7(H7), C14(H14), C19(H19A,H19B,H19C), C12(H12), C18(H18A,H18B,H18C), C9(H9A,
 H9B,H9C)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C20(H20A,H20B), C23(H23A,H23B), C22(H22A,H22B), C31(H31A,
 H31B), C30(H30A,H30B), C33(H33A,H33B), C32(H32A,H32B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.31364(4) -0.01742(2) 0.41925(2) 0.02383(11) Uani 1 1 d . . . . .
Br1 Br 0.1991(9) -0.1361(7) 0.4243(6) 0.0271(6) Uani 0.5 1 d . . P A 1
Cl1 Cl 0.215(2) -0.1366(17) 0.4259(15) 0.0271(6) Uani 0.5 1 d . . P A 2
N3 N 0.3594(3) 0.16133(15) 0.43597(14) 0.0201(5) Uani 1 1 d . . . . .
N1 N 0.4929(3) 0.10797(15) 0.37478(14) 0.0185(5) Uani 1 1 d . . . . .
N2 N 0.4418(3) 0.22546(15) 0.42096(15) 0.0214(5) Uani 1 1 d . . . . .
C10 C 0.6263(3) 0.23724(18) 0.35230(18) 0.0214(6) Uani 1 1 d . . . . .
C4 C 0.7264(3) 0.04202(18) 0.37057(18) 0.0215(6) Uani 1 1 d . . . . .
H4 H 0.7858 0.0741 0.4138 0.026 Uiso 1 1 d R . . . .
C1 C 0.3890(3) 0.08834(18) 0.41050(17) 0.0201(6) Uani 1 1 d . . . . .
C3 C 0.5660(3) 0.04913(17) 0.33968(17) 0.0184(6) Uani 1 1 d . . . . .
C16 C 0.2589(3) 0.18113(19) 0.48317(18) 0.0230(6) Uani 1 1 d . . . . .
C2 C 0.5230(3) 0.19093(18) 0.38292(17) 0.0199(6) Uani 1 1 d . . . . .
C8 C 0.4761(3) 0.00187(19) 0.27542(19) 0.0241(6) Uani 1 1 d . . . . .
H8 H 0.3684 0.0070 0.2546 0.029 Uiso 1 1 d R . . . .
C5 C 0.7962(3) -0.01365(19) 0.33619(18) 0.0235(6) Uani 1 1 d . . . . .
H5 H 0.9039 -0.0188 0.3569 0.028 Uiso 1 1 d R . . . .
C17 C 0.3630(4) 0.1822(2) 0.57102(19) 0.0359(8) Uani 1 1 d . . . . .
H17A H 0.4142 0.1300 0.5848 0.043 Uiso 1 1 d R . . . .
H17B H 0.3016 0.1917 0.6034 0.043 Uiso 1 1 d R . . . .
H17C H 0.4393 0.2249 0.5806 0.043 Uiso 1 1 d R . . . .
C13 C 0.8072(4) 0.3344(2) 0.2937(2) 0.0342(8) Uani 1 1 d . . . . .
H13 H 0.8664 0.3681 0.2741 0.041 Uiso 1 1 d R . . . .
C11 C 0.7211(3) 0.2976(2) 0.4008(2) 0.0270(7) Uani 1 1 d . . . . .
H11 H 0.7244 0.3057 0.4528 0.032 Uiso 1 1 d R . . . .
C6 C 0.7093(4) -0.06216(18) 0.27131(18) 0.0237(6) Uani 1 1 d . . . . .
C15 C 0.6237(4) 0.2253(2) 0.2752(2) 0.0282(7) Uani 1 1 d . . . . .
H15 H 0.5608 0.1847 0.2429 0.034 Uiso 1 1 d R . . . .
C7 C 0.5500(4) -0.0538(2) 0.24234(19) 0.0277(7) Uani 1 1 d . . . . .
H7 H 0.4905 -0.0866 0.1997 0.033 Uiso 1 1 d R . . . .
C14 C 0.7145(4) 0.2741(2) 0.2463(2) 0.0324(8) Uani 1 1 d . . . . .
H14 H 0.7143 0.2659 0.1949 0.039 Uiso 1 1 d R . . . .
C19 C 0.1871(4) 0.2654(2) 0.4564(2) 0.0407(9) Uani 1 1 d . . . . .
H19A H 0.2676 0.3054 0.4641 0.049 Uiso 1 1 d R . . . .
H19B H 0.1264 0.2802 0.4878 0.049 Uiso 1 1 d R . . . .
H19C H 0.1213 0.2635 0.4007 0.049 Uiso 1 1 d R . . . .
C12 C 0.8114(4) 0.3464(2) 0.3711(2) 0.0329(8) Uani 1 1 d . . . . .
H12 H 0.8752 0.3869 0.4031 0.040 Uiso 1 1 d R . . . .
C18 C 0.1322(4) 0.1180(2) 0.4672(2) 0.0400(9) Uani 1 1 d . . . . .
H18A H 0.0701 0.1186 0.4110 0.048 Uiso 1 1 d R . . . .
H18B H 0.0682 0.1310 0.4974 0.048 Uiso 1 1 d R . . . .
H18C H 0.1768 0.0644 0.4822 0.048 Uiso 1 1 d R . . . .
C9 C 0.7876(4) -0.1225(2) 0.2346(2) 0.0373(8) Uani 1 1 d . . . . .
H9A H 0.7388 -0.1753 0.2300 0.045 Uiso 1 1 d R . . . .
H9B H 0.8949 -0.1267 0.2691 0.045 Uiso 1 1 d R . . . .
H9C H 0.7809 -0.1042 0.1825 0.045 Uiso 1 1 d R . . . .
O1 O 0.0764(15) 0.0298(6) 0.1597(10) 0.063(3) Uani 0.603(14) 1 d D . P B 1
C21 C 0.050(2) 0.1563(10) 0.2187(9) 0.055(3) Uani 0.603(14) 1 d D . P B 1
H21A H 0.1300 0.1700 0.2715 0.066 Uiso 0.603(14) 1 calc R . P B 1
H21B H -0.0436 0.1901 0.2105 0.066 Uiso 0.603(14) 1 calc R . P B 1
C20 C 0.011(3) 0.0660(10) 0.2134(12) 0.056(2) Uani 0.603(14) 1 d D . P B 1
H20A H 0.0560 0.0402 0.2670 0.067 Uiso 0.603(14) 1 calc R . P B 1
H20B H -0.1028 0.0581 0.1927 0.067 Uiso 0.603(14) 1 calc R . P B 1
C23 C 0.0935(16) 0.0914(8) 0.1096(7) 0.066(3) Uani 0.603(14) 1 d D . P B 1
H23A H 0.0011 0.0930 0.0593 0.079 Uiso 0.603(14) 1 calc R . P B 1
H23B H 0.1862 0.0804 0.0959 0.079 Uiso 0.603(14) 1 calc R . P B 1
C22 C 0.1109(18) 0.1701(6) 0.1520(8) 0.071(3) Uani 0.603(14) 1 d D . P B 1
H22A H 0.0504 0.2136 0.1151 0.086 Uiso 0.603(14) 1 calc R . P B 1
H22B H 0.2215 0.1868 0.1742 0.086 Uiso 0.603(14) 1 calc R . P B 1
O2 O 0.021(2) 0.0314(10) 0.1542(16) 0.063(3) Uani 0.397(14) 1 d D . P B 2
C31 C 0.082(4) 0.1559(16) 0.2253(12) 0.055(3) Uani 0.397(14) 1 d D . P B 2
H31A H 0.1966 0.1563 0.2500 0.066 Uiso 0.397(14) 1 calc R . P B 2
H31B H 0.0386 0.1957 0.2533 0.066 Uiso 0.397(14) 1 calc R . P B 2
C30 C 0.016(5) 0.0698(16) 0.2252(18) 0.056(2) Uani 0.397(14) 1 d D . P B 2
H30A H 0.0804 0.0390 0.2736 0.067 Uiso 0.397(14) 1 calc R . P B 2
H30B H -0.0918 0.0726 0.2238 0.067 Uiso 0.397(14) 1 calc R . P B 2
C33 C 0.029(2) 0.0907(12) 0.0998(12) 0.066(3) Uani 0.397(14) 1 d D . P B 2
H33A H -0.0601 0.0848 0.0484 0.079 Uiso 0.397(14) 1 calc R . P B 2
H33B H 0.1262 0.0841 0.0892 0.079 Uiso 0.397(14) 1 calc R . P B 2
C32 C 0.025(3) 0.1734(10) 0.1354(12) 0.071(3) Uani 0.397(14) 1 d D . P B 2
H32A H -0.0812 0.1963 0.1156 0.086 Uiso 0.397(14) 1 calc R . P B 2
H32B H 0.0956 0.2123 0.1229 0.086 Uiso 0.397(14) 1 calc R . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Br1 2.220(10) . ?
Cu1 Cl1 2.16(3) . ?
Cu1 C1 1.884(3) . ?
N3 N2 1.376(3) . ?
N3 C1 1.336(4) . ?
N3 C16 1.502(4) . ?
N1 C1 1.372(4) . ?
N1 C3 1.442(4) . ?
N1 C2 1.375(4) . ?
N2 C2 1.311(4) . ?
C10 C2 1.470(4) . ?
C10 C11 1.390(4) . ?
C10 C15 1.386(4) . ?
C4 H4 0.9298 . ?
C4 C3 1.385(4) . ?
C4 C5 1.381(4) . ?
C3 C8 1.381(4) . ?
C16 C17 1.515(4) . ?
C16 C19 1.522(4) . ?
C16 C18 1.505(5) . ?
C8 H8 0.9303 . ?
C8 C7 1.390(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(4) . ?
C17 H17A 0.9599 . ?
C17 H17B 0.9604 . ?
C17 H17C 0.9597 . ?
C13 H13 0.9297 . ?
C13 C14 1.374(5) . ?
C13 C12 1.387(5) . ?
C11 H11 0.9304 . ?
C11 C12 1.390(5) . ?
C6 C7 1.378(4) . ?
C6 C9 1.506(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.386(4) . ?
C7 H7 0.9298 . ?
C14 H14 0.9299 . ?
C19 H19A 0.9598 . ?
C19 H19B 0.9602 . ?
C19 H19C 0.9600 . ?
C12 H12 0.9301 . ?
C18 H18A 0.9601 . ?
C18 H18B 0.9602 . ?
C18 H18C 0.9600 . ?
C9 H9A 0.9601 . ?
C9 H9B 0.9601 . ?
C9 H9C 0.9598 . ?
O1 C20 1.435(9) . ?
O1 C23 1.392(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C20 1.507(8) . ?
C21 C22 1.513(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C22 1.468(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O2 C30 1.432(9) . ?
O2 C33 1.395(9) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C30 1.525(9) . ?
C31 C32 1.526(10) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C32 1.495(9) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?

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 Cu1 Br1 173.8(2) . . ?
C1 Cu1 Cl1 177.1(6) . . ?
N2 N3 C16 116.6(2) . . ?
C1 N3 N2 114.2(2) . . ?
C1 N3 C16 129.0(2) . . ?
C1 N1 C3 124.6(2) . . ?
C1 N1 C2 109.2(2) . . ?
C2 N1 C3 126.1(2) . . ?
C2 N2 N3 103.9(2) . . ?
C11 C10 C2 118.4(3) . . ?
C15 C10 C2 121.5(3) . . ?
C15 C10 C11 119.9(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.7 . . ?
C5 C4 C3 118.9(3) . . ?
N3 C1 Cu1 130.9(2) . . ?
N3 C1 N1 102.6(2) . . ?
N1 C1 Cu1 126.5(2) . . ?
C4 C3 N1 119.0(2) . . ?
C8 C3 N1 119.9(2) . . ?
C8 C3 C4 121.1(3) . . ?
N3 C16 C17 107.4(2) . . ?
N3 C16 C19 107.7(2) . . ?
N3 C16 C18 110.2(3) . . ?
C17 C16 C19 110.8(3) . . ?
C18 C16 C17 111.1(3) . . ?
C18 C16 C19 109.6(3) . . ?
N1 C2 C10 126.7(3) . . ?
N2 C2 N1 110.1(2) . . ?
N2 C2 C10 123.2(3) . . ?
C3 C8 H8 121.0 . . ?
C3 C8 C7 118.6(3) . . ?
C7 C8 H8 120.5 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 109.7 . . ?
C16 C17 H17C 109.9 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.4 . . ?
C14 C13 H13 120.5 . . ?
C14 C13 C12 120.1(3) . . ?
C12 C13 H13 119.4 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 119.9 . . ?
C5 C6 C9 120.8(3) . . ?
C7 C6 C5 118.0(3) . . ?
C7 C6 C9 121.2(3) . . ?
C10 C15 H15 119.9 . . ?
C10 C15 C14 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C8 C7 H7 119.3 . . ?
C6 C7 C8 121.9(3) . . ?
C6 C7 H7 118.8 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C19 H19A 109.9 . . ?
C16 C19 H19B 108.8 . . ?
C16 C19 H19C 109.7 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 120.2 . . ?
C16 C18 H18A 108.6 . . ?
C16 C18 H18B 109.8 . . ?
C16 C18 H18C 110.0 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 108.3 . . ?
C6 C9 H9C 110.6 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C23 O1 C20 108.2(6) . . ?
H21A C21 H21B 109.0 . . ?
C20 C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
C20 C21 C22 104.1(5) . . ?
C22 C21 H21A 110.9 . . ?
C22 C21 H21B 110.9 . . ?
O1 C20 C21 107.1(7) . . ?
O1 C20 H20A 110.3 . . ?
O1 C20 H20B 110.3 . . ?
C21 C20 H20A 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.5 . . ?
O1 C23 H23A 110.1 . . ?
O1 C23 H23B 110.1 . . ?
O1 C23 C22 108.1(6) . . ?
H23A C23 H23B 108.4 . . ?
C22 C23 H23A 110.1 . . ?
C22 C23 H23B 110.1 . . ?
C21 C22 H22A 110.5 . . ?
C21 C22 H22B 110.5 . . ?
C23 C22 C21 106.1(5) . . ?
C23 C22 H22A 110.5 . . ?
C23 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
C33 O2 C30 110.2(8) . . ?
H31A C31 H31B 109.4 . . ?
C30 C31 H31A 111.6 . . ?
C30 C31 H31B 111.6 . . ?
C30 C31 C32 100.9(9) . . ?
C32 C31 H31A 111.6 . . ?
C32 C31 H31B 111.6 . . ?
O2 C30 C31 105.1(8) . . ?
O2 C30 H30A 110.7 . . ?
O2 C30 H30B 110.7 . . ?
C31 C30 H30A 110.7 . . ?
C31 C30 H30B 110.7 . . ?
H30A C30 H30B 108.8 . . ?
O2 C33 H33A 110.1 . . ?
O2 C33 H33B 110.1 . . ?
O2 C33 C32 108.0(7) . . ?
H33A C33 H33B 108.4 . . ?
C32 C33 H33A 110.1 . . ?
C32 C33 H33B 110.1 . . ?
C31 C32 H32A 111.1 . . ?
C31 C32 H32B 111.1 . . ?
C33 C32 C31 103.3(7) . . ?
C33 C32 H32A 111.1 . . ?
C33 C32 H32B 111.1 . . ?
H32A C32 H32B 109.1 . . ?

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
N3 N2 C2 N1 -0.3(3) . . . . ?
N3 N2 C2 C10 178.0(3) . . . . ?
N1 C3 C8 C7 179.4(3) . . . . ?
N2 N3 C1 Cu1 177.7(2) . . . . ?
N2 N3 C1 N1 -2.0(3) . . . . ?
N2 N3 C16 C17 -81.5(3) . . . . ?
N2 N3 C16 C19 37.9(3) . . . . ?
N2 N3 C16 C18 157.4(3) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C10 C15 C14 C13 -0.1(5) . . . . ?
C4 C3 C8 C7 0.4(4) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C4 C5 C6 C9 180.0(3) . . . . ?
C1 N3 N2 C2 1.5(3) . . . . ?
C1 N3 C16 C17 93.5(4) . . . . ?
C1 N3 C16 C19 -147.1(3) . . . . ?
C1 N3 C16 C18 -27.6(4) . . . . ?
C1 N1 C3 C4 -118.9(3) . . . . ?
C1 N1 C3 C8 62.1(4) . . . . ?
C1 N1 C2 N2 -1.0(3) . . . . ?
C1 N1 C2 C10 -179.2(3) . . . . ?
C3 N1 C1 Cu1 -2.0(4) . . . . ?
C3 N1 C1 N3 177.7(2) . . . . ?
C3 N1 C2 N2 -176.8(2) . . . . ?
C3 N1 C2 C10 5.0(4) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C3 C8 C7 C6 -0.7(5) . . . . ?
C16 N3 N2 C2 177.2(2) . . . . ?
C16 N3 C1 Cu1 2.6(4) . . . . ?
C16 N3 C1 N1 -177.1(3) . . . . ?
C2 N1 C1 Cu1 -178.0(2) . . . . ?
C2 N1 C1 N3 1.8(3) . . . . ?
C2 N1 C3 C4 56.3(4) . . . . ?
C2 N1 C3 C8 -122.7(3) . . . . ?
C2 C10 C11 C12 -175.3(3) . . . . ?
C2 C10 C15 C14 175.4(3) . . . . ?
C5 C4 C3 N1 -179.2(3) . . . . ?
C5 C4 C3 C8 -0.2(4) . . . . ?
C5 C6 C7 C8 0.8(5) . . . . ?
C11 C10 C2 N1 -139.1(3) . . . . ?
C11 C10 C2 N2 43.0(4) . . . . ?
C11 C10 C15 C14 -0.6(5) . . . . ?
C15 C10 C2 N1 44.9(4) . . . . ?
C15 C10 C2 N2 -133.1(3) . . . . ?
C15 C10 C11 C12 0.8(4) . . . . ?
C14 C13 C12 C11 -0.4(5) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C9 C6 C7 C8 -179.8(3) . . . . ?
O1 C23 C22 C21 -18.6(14) . . . . ?
C20 O1 C23 C22 26.5(15) . . . . ?
C20 C21 C22 C23 4.0(17) . . . . ?
C23 O1 C20 C21 -23.6(19) . . . . ?
C22 C21 C20 O1 11(2) . . . . ?
O2 C33 C32 C31 23(2) . . . . ?
C30 O2 C33 C32 -2(3) . . . . ?
C30 C31 C32 C33 -33(2) . . . . ?
C33 O2 C30 C31 -20(3) . . . . ?
C32 C31 C30 O2 33(3) . . . . ?



_database_code_depnum_ccdc_archive 'CCDC 1011249'
