# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c252
_database_code_depnum_ccdc_archive 'CCDC 1471431'
_audit_update_record             
;
2016-03-30 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 Au N5 S'
_chemical_formula_weight         643.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   11.8017(3)
_cell_length_b                   12.0237(2)
_cell_length_c                   17.0165(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.109(2)
_cell_angle_gamma                90.00
_cell_volume                     2319.83(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    28330
_cell_measurement_theta_min      4.1771
_cell_measurement_theta_max      28.8202

_exptl_crystal_description       Tablet
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    6.458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3063
_exptl_absorpt_correction_T_max  0.9265
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.0655
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            53563
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.19
_diffrn_reflns_theta_max         25.49
_reflns_number_total             4293
_reflns_number_gt                3901
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0316P)²+2.4933P] 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         4293
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0562
_refine_ls_wR_factor_gt          0.0543
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.394228(12) 0.048053(10) 0.063360(8) 0.03029(6) Uani 1 1 d . . .
S1 S 0.43782(13) -0.03751(8) 0.18801(6) 0.0514(3) Uani 1 1 d . . .
N1 N 0.2961(3) 0.0820(3) -0.12016(19) 0.0384(7) Uani 1 1 d . . .
N2 N 0.3671(3) 0.2318(2) -0.05929(16) 0.0300(6) Uani 1 1 d . . .
N3 N 0.1103(4) -0.1659(3) -0.1760(2) 0.0569(10) Uani 1 1 d . . .
N4 N 0.5727(3) 0.4487(2) 0.12263(17) 0.0289(6) Uani 1 1 d . . .
N5 N 0.4953(3) 0.0294(2) 0.34019(19) 0.0347(7) Uani 1 1 d . . .
C1 C 0.3513(3) 0.1228(3) -0.0462(2) 0.0303(7) Uani 1 1 d . . .
C2 C 0.2779(4) 0.1639(3) -0.1790(2) 0.0503(11) Uani 1 1 d . . .
H2 H 0.2405 0.1549 -0.2357 0.060 Uiso 1 1 calc R . .
C3 C 0.3227(4) 0.2586(3) -0.1414(2) 0.0440(9) Uani 1 1 d . . .
H3 H 0.3239 0.3294 -0.1660 0.053 Uiso 1 1 calc R . .
C4 C 0.2691(4) -0.0358(3) -0.1367(3) 0.0473(10) Uani 1 1 d . . .
H4A H 0.3253 -0.0804 -0.0944 0.057 Uiso 1 1 calc R . .
H4B H 0.2817 -0.0547 -0.1902 0.057 Uiso 1 1 calc R . .
C5 C 0.1448(4) -0.0690(3) -0.1380(2) 0.0385(9) Uani 1 1 d . . .
C6 C 0.0758(3) -0.0055(3) -0.1019(2) 0.0340(8) Uani 1 1 d . . .
H6 H 0.1044 0.0626 -0.0755 0.041 Uiso 1 1 calc R . .
C7 C -0.0341(4) -0.0423(3) -0.1049(2) 0.0457(10) Uani 1 1 d . . .
H7 H -0.0833 0.0005 -0.0809 0.055 Uiso 1 1 calc R . .
C8 C -0.0742(5) -0.1418(4) -0.1428(2) 0.0595(13) Uani 1 1 d . . .
H8 H -0.1511 -0.1681 -0.1455 0.071 Uiso 1 1 calc R . .
C9 C -0.0001(6) -0.2023(3) -0.1767(3) 0.0702(17) Uani 1 1 d . . .
H9 H -0.0266 -0.2718 -0.2016 0.084 Uiso 1 1 calc R . .
C10 C 0.4356(3) 0.3057(3) 0.00297(19) 0.0263(7) Uani 1 1 d . . .
C11 C 0.5545(3) 0.3205(3) 0.0073(2) 0.0293(7) Uani 1 1 d . . .
C12 C 0.6119(3) 0.2679(3) -0.0454(2) 0.0359(8) Uani 1 1 d . . .
H12 H 0.5686 0.2204 -0.0878 0.043 Uiso 1 1 calc R . .
C13 C 0.7289(4) 0.2850(3) -0.0356(2) 0.0422(9) Uani 1 1 d . . .
H13 H 0.7673 0.2484 -0.0705 0.051 Uiso 1 1 calc R . .
C14 C 0.7939(3) 0.3575(3) 0.0266(2) 0.0424(9) Uani 1 1 d . . .
H14 H 0.8756 0.3684 0.0327 0.051 Uiso 1 1 calc R . .
C15 C 0.7422(3) 0.4111(3) 0.0773(2) 0.0358(8) Uani 1 1 d . . .
H15 H 0.7874 0.4599 0.1179 0.043 Uiso 1 1 calc R . .
C16 C 0.6199(3) 0.3947(3) 0.0701(2) 0.0281(7) Uani 1 1 d . . .
C17 C 0.4576(3) 0.4314(3) 0.1163(2) 0.0262(7) Uani 1 1 d . . .
C18 C 0.4068(3) 0.4886(3) 0.1714(2) 0.0306(7) Uani 1 1 d . . .
H18 H 0.4535 0.5395 0.2097 0.037 Uiso 1 1 calc R . .
C19 C 0.2926(3) 0.4718(3) 0.1701(2) 0.0335(8) Uani 1 1 d . . .
H19 H 0.2607 0.5095 0.2082 0.040 Uiso 1 1 calc R . .
C20 C 0.2205(3) 0.3982(3) 0.1122(2) 0.0317(8) Uani 1 1 d . . .
H20 H 0.1405 0.3874 0.1117 0.038 Uiso 1 1 calc R . .
C21 C 0.2645(3) 0.3431(3) 0.0577(2) 0.0296(7) Uani 1 1 d . . .
H21 H 0.2152 0.2938 0.0194 0.036 Uiso 1 1 calc R . .
C22 C 0.3839(3) 0.3582(3) 0.05717(18) 0.0247(7) Uani 1 1 d . . .
C23 C 0.4604(3) 0.0670(3) 0.2632(2) 0.0324(8) Uani 1 1 d . . .
C24 C 0.4405(4) 0.1800(3) 0.2469(2) 0.0435(9) Uani 1 1 d . . .
H24 H 0.4163 0.2059 0.1920 0.052 Uiso 1 1 calc R . .
C25 C 0.4560(4) 0.2532(3) 0.3101(3) 0.0552(12) Uani 1 1 d . . .
H25 H 0.4418 0.3304 0.3000 0.066 Uiso 1 1 calc R . .
C26 C 0.4928(3) 0.2131(3) 0.3893(2) 0.0423(9) Uani 1 1 d . . .
H26 H 0.5059 0.2622 0.4346 0.051 Uiso 1 1 calc R . .
C27 C 0.5095(3) 0.1042(3) 0.4006(2) 0.0335(8) Uani 1 1 d . . .
H27 H 0.5332 0.0775 0.4553 0.040 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 2.003(3) . ?
Au1 S1 2.2840(10) . ?
S1 C23 1.760(4) . ?
N1 C1 1.340(4) . ?
N1 C2 1.378(5) . ?
N1 C4 1.462(5) . ?
N2 C1 1.350(4) . ?
N2 C3 1.388(4) . ?
N2 C10 1.446(4) . ?
N3 C5 1.340(5) . ?
N3 C9 1.371(7) . ?
N4 C16 1.344(4) . ?
N4 C17 1.349(4) . ?
N5 C23 1.338(5) . ?
N5 C27 1.340(5) . ?
C2 C3 1.340(6) . ?
C4 C5 1.514(6) . ?
C5 C6 1.379(5) . ?
C6 C7 1.357(6) . ?
C7 C8 1.379(6) . ?
C8 C9 1.381(8) . ?
C10 C22 1.390(4) . ?
C10 C11 1.396(5) . ?
C11 C12 1.414(5) . ?
C11 C16 1.441(5) . ?
C12 C13 1.359(5) . ?
C13 C14 1.420(6) . ?
C14 C15 1.350(5) . ?
C15 C16 1.427(5) . ?
C17 C18 1.423(5) . ?
C17 C22 1.435(4) . ?
C18 C19 1.357(5) . ?
C19 C20 1.418(5) . ?
C20 C21 1.356(5) . ?
C21 C22 1.423(4) . ?
C23 C24 1.394(5) . ?
C24 C25 1.362(6) . ?
C25 C26 1.382(5) . ?
C26 C27 1.330(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Au1 S1 178.44(10) . . ?
C23 S1 Au1 107.64(12) . . ?
C1 N1 C2 111.0(3) . . ?
C1 N1 C4 124.0(3) . . ?
C2 N1 C4 124.8(3) . . ?
C1 N2 C3 111.2(3) . . ?
C1 N2 C10 123.4(3) . . ?
C3 N2 C10 124.9(3) . . ?
C5 N3 C9 116.3(4) . . ?
C16 N4 C17 117.8(3) . . ?
C23 N5 C27 117.6(3) . . ?
N1 C1 N2 104.7(3) . . ?
N1 C1 Au1 129.9(3) . . ?
N2 C1 Au1 125.3(2) . . ?
C3 C2 N1 107.4(3) . . ?
C2 C3 N2 105.7(3) . . ?
N1 C4 C5 114.6(3) . . ?
N3 C5 C6 123.9(4) . . ?
N3 C5 C4 113.6(4) . . ?
C6 C5 C4 122.5(3) . . ?
C7 C6 C5 118.6(3) . . ?
C6 C7 C8 120.1(4) . . ?
C7 C8 C9 118.5(4) . . ?
N3 C9 C8 122.6(4) . . ?
C22 C10 C11 121.8(3) . . ?
C22 C10 N2 120.4(3) . . ?
C11 C10 N2 117.8(3) . . ?
C10 C11 C12 124.2(3) . . ?
C10 C11 C16 116.2(3) . . ?
C12 C11 C16 119.7(3) . . ?
C13 C12 C11 120.2(4) . . ?
C12 C13 C14 120.3(4) . . ?
C15 C14 C13 121.5(4) . . ?
C14 C15 C16 120.3(4) . . ?
N4 C16 C15 118.1(3) . . ?
N4 C16 C11 123.9(3) . . ?
C15 C16 C11 118.0(3) . . ?
N4 C17 C18 118.2(3) . . ?
N4 C17 C22 123.5(3) . . ?
C18 C17 C22 118.3(3) . . ?
C19 C18 C17 121.0(3) . . ?
C18 C19 C20 120.4(3) . . ?
C21 C20 C19 120.7(3) . . ?
C20 C21 C22 120.7(3) . . ?
C10 C22 C21 124.3(3) . . ?
C10 C22 C17 116.8(3) . . ?
C21 C22 C17 118.9(3) . . ?
N5 C23 C24 120.9(3) . . ?
N5 C23 S1 114.4(3) . . ?
C24 C23 S1 124.6(3) . . ?
C25 C24 C23 119.6(4) . . ?
C24 C25 C26 118.8(4) . . ?
C27 C26 C25 118.6(4) . . ?
C26 C27 N5 124.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.089
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.090
