# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc1pvx9r
_database_code_depnum_ccdc_archive 'CCDC 1574995'
loop_
_audit_author_name
_audit_author_address
'Reza Halvagar'
;CCERCI
Iran
;
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

_audit_creation_date             2019-07-16T09:11:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 Au N2 P S2'
_chemical_formula_sum            'C20 H18 Au N2 P S2'
_chemical_formula_weight         578.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?
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                   12.258(3)
_cell_length_b                   9.6261(19)
_cell_length_c                   18.107(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.71(3)
_cell_angle_gamma                90
_cell_volume                     2056.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9366
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      26.73

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      293(2)
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_F_000             1112
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -3 -6 0.153
-6 2 3 0.163
2 2 -5 0.12
-2 -2 5 0.146
3 -1 -1 0.098
-3 1 1 0.15
-5 -2 -4 0.144
7 -3 -2 0.106
-1 4 -6 0.133
1 -3 4 0.134
2 1 2 0.023

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    7.44
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.6259
_exptl_absorpt_correction_T_max  0.7651
_shelx_estimated_absorpt_T_min   0.199
_shelx_estimated_absorpt_T_max   0.422
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_av_R_equivalents  0.1808
_diffrn_reflns_number            14476
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.803
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             3636
_reflns_number_gt                2349
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows version 2014.1'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0308P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3636
_refine_ls_number_parameters     235
_refine_ls_number_restraints     230
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_restrained_S_all      0.852
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.1
_refine_diff_density_min         -2.546
_refine_diff_density_rms         0.158

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.013 8.802 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.102 0.094 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.125 0.123 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6222(9) 0.3050(10) -0.0157(6) 0.053(2) Uani 1 d . .
C2 C 0.5233(10) 0.2422(12) -0.0237(8) 0.072(3) Uani 1 d . .
H5 H 0.5177 0.1677 0.0078 0.086 Uiso 1 calc . .
C3 C 0.4302(12) 0.2869(15) -0.0781(10) 0.096(4) Uani 1 d . .
H4 H 0.3611 0.2431 -0.0827 0.115 Uiso 1 calc . .
C4 C 0.4356(12) 0.3951(14) -0.1263(9) 0.090(4) Uani 1 d . .
H3 H 0.3716 0.4251 -0.1634 0.108 Uiso 1 calc . .
C5 C 0.5380(12) 0.4567(14) -0.1177(9) 0.093(4) Uani 1 d . .
H2 H 0.5441 0.5307 -0.1494 0.112 Uiso 1 calc . .
C6 C 0.6354(11) 0.4105(11) -0.0615(8) 0.070(3) Uani 1 d . .
H1 H 0.7058 0.4513 -0.0564 0.084 Uiso 1 calc . .
C7 C 0.7759(9) 0.0646(10) 0.0271(7) 0.056(2) Uani 1 d . .
C8 C 0.8784(11) 0.0082(12) 0.0587(9) 0.080(3) Uani 1 d . .
H10 H 0.9318 0.0583 0.0953 0.096 Uiso 1 calc . .
C9 C 0.9064(14) -0.1232(14) 0.0380(10) 0.091(4) Uani 1 d . .
H9 H 0.9785 -0.1587 0.0599 0.109 Uiso 1 calc . .
C10 C 0.8336(15) -0.1961(13) -0.0113(11) 0.095(4) Uani 1 d . .
H8 H 0.853 -0.2857 -0.0222 0.114 Uiso 1 calc . .
C11 C 0.7252(17) -0.1443(14) -0.0492(11) 0.111(5) Uani 1 d . .
H7 H 0.6742 -0.1959 -0.0865 0.133 Uiso 1 calc . .
N2 N 0.6968(12) -0.0056(13) -0.0271(9) 0.114(4) Uani 1 d . .
C13 C 0.6958(9) 0.2159(10) 0.1419(7) 0.055(2) Uani 1 d . .
C14 C 0.6207(11) 0.1097(12) 0.1448(8) 0.075(3) Uani 1 d . .
H15 H 0.5996 0.046 0.1048 0.09 Uiso 1 calc . .
C15 C 0.5783(12) 0.0995(15) 0.2063(9) 0.092(4) Uani 1 d . .
H14 H 0.5267 0.0295 0.2081 0.111 Uiso 1 calc . .
C16 C 0.6114(13) 0.1932(15) 0.2670(9) 0.085(4) Uani 1 d . .
H13 H 0.5829 0.1855 0.3095 0.103 Uiso 1 calc . .
C17 C 0.6861(12) 0.2963(15) 0.2633(8) 0.080(3) Uani 1 d . .
H12 H 0.7081 0.3598 0.3033 0.096 Uiso 1 calc . .
C18 C 0.7283(10) 0.3067(12) 0.2018(7) 0.065(3) Uani 1 d . .
H11 H 0.78 0.3766 0.2003 0.078 Uiso 1 calc . .
C19 C 1.1519(9) 0.4241(12) 0.1804(7) 0.061(2) Uani 1 d . .
C20 C 1.2335(16) 0.298(2) 0.3067(11) 0.128(6) Uani 1 d . .
H20A H 1.2317 0.3505 0.3522 0.154 Uiso 1 calc . .
H20B H 1.2538 0.2027 0.3211 0.154 Uiso 1 calc . .
C21 C 1.3094(17) 0.358(2) 0.2702(13) 0.158(8) Uani 1 d . .
H21A H 1.3552 0.2843 0.2574 0.189 Uiso 1 calc . .
H21B H 1.3599 0.4192 0.3063 0.189 Uiso 1 calc . .
Au1 Au 0.90053(3) 0.37762(4) 0.07788(3) 0.05258(15) Uani 1 d . .
N1 N 1.2553(10) 0.4397(17) 0.1975(9) 0.120(5) Uani 1 d . .
P1 P 0.7464(2) 0.2393(3) 0.05681(17) 0.0504(6) Uani 1 d . .
S1 S 1.0628(2) 0.5111(2) 0.10171(16) 0.0535(6) Uani 1 d . .
S2 S 1.0987(4) 0.3076(4) 0.2350(3) 0.0969(13) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.327(15) . ?
C1 C6 1.349(15) . ?
C1 P1 1.832(11) . ?
C2 C3 1.359(19) . ?
C2 H5 0.93 . ?
C3 C4 1.372(19) . ?
C3 H4 0.93 . ?
C4 C5 1.358(18) . ?
C4 H3 0.93 . ?
C5 C6 1.415(19) . ?
C5 H2 0.93 . ?
C6 H1 0.93 . ?
C7 C8 1.347(17) . ?
C7 N2 1.358(18) . ?
C7 P1 1.831(10) . ?
C8 C9 1.388(17) . ?
C8 H10 0.93 . ?
C9 C10 1.29(2) . ?
C9 H9 0.93 . ?
C10 C11 1.41(2) . ?
C10 H8 0.93 . ?
C11 N2 1.463(18) . ?
C11 H7 0.93 . ?
C13 C18 1.366(16) . ?
C13 C14 1.387(14) . ?
C13 P1 1.824(10) . ?
C14 C15 1.355(18) . ?
C14 H15 0.93 . ?
C15 C16 1.39(2) . ?
C15 H14 0.93 . ?
C16 C17 1.364(19) . ?
C16 H13 0.93 . ?
C17 C18 1.351(15) . ?
C17 H12 0.93 . ?
C18 H11 0.93 . ?
C19 N1 1.230(15) . ?
C19 S2 1.735(12) . ?
C19 S1 1.755(12) . ?
C20 C21 1.40(2) . ?
C20 S2 1.805(19) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C21 N1 1.52(2) . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
Au1 P1 2.258(3) . ?
Au1 S1 2.309(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.2(12) . . ?
C2 C1 P1 118.6(8) . . ?
C6 C1 P1 119.1(9) . . ?
C1 C2 C3 119.9(12) . . ?
C1 C2 H5 120.1 . . ?
C3 C2 H5 120.1 . . ?
C2 C3 C4 121.7(14) . . ?
C2 C3 H4 119.2 . . ?
C4 C3 H4 119.2 . . ?
C5 C4 C3 117.5(13) . . ?
C5 C4 H3 121.2 . . ?
C3 C4 H3 121.2 . . ?
C4 C5 C6 121.2(12) . . ?
C4 C5 H2 119.4 . . ?
C6 C5 H2 119.4 . . ?
C1 C6 C5 117.5(12) . . ?
C1 C6 H1 121.3 . . ?
C5 C6 H1 121.3 . . ?
C8 C7 N2 120.5(10) . . ?
C8 C7 P1 118.8(9) . . ?
N2 C7 P1 120.7(9) . . ?
C7 C8 C9 121.5(15) . . ?
C7 C8 H10 119.2 . . ?
C9 C8 H10 119.2 . . ?
C10 C9 C8 120.6(16) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 122.0(12) . . ?
C9 C10 H8 119 . . ?
C11 C10 H8 119 . . ?
C10 C11 N2 116.9(15) . . ?
C10 C11 H7 121.6 . . ?
N2 C11 H7 121.6 . . ?
C7 N2 C11 118.4(14) . . ?
C18 C13 C14 119.8(10) . . ?
C18 C13 P1 120.0(8) . . ?
C14 C13 P1 120.2(9) . . ?
C15 C14 C13 119.4(13) . . ?
C15 C14 H15 120.3 . . ?
C13 C14 H15 120.3 . . ?
C14 C15 C16 120.4(13) . . ?
C14 C15 H14 119.8 . . ?
C16 C15 H14 119.8 . . ?
C17 C16 C15 119.2(12) . . ?
C17 C16 H13 120.4 . . ?
C15 C16 H13 120.4 . . ?
C18 C17 C16 120.4(14) . . ?
C18 C17 H12 119.8 . . ?
C16 C17 H12 119.8 . . ?
C17 C18 C13 120.8(12) . . ?
C17 C18 H11 119.6 . . ?
C13 C18 H11 119.6 . . ?
N1 C19 S2 117.2(10) . . ?
N1 C19 S1 121.2(10) . . ?
S2 C19 S1 121.6(6) . . ?
C21 C20 S2 103.6(13) . . ?
C21 C20 H20A 111 . . ?
S2 C20 H20A 111 . . ?
C21 C20 H20B 111 . . ?
S2 C20 H20B 111 . . ?
H20A C20 H20B 109 . . ?
C20 C21 N1 115.5(15) . . ?
C20 C21 H21A 108.4 . . ?
N1 C21 H21A 108.4 . . ?
C20 C21 H21B 108.4 . . ?
N1 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
P1 Au1 S1 177.56(10) . . ?
C19 N1 C21 109.3(13) . . ?
C13 P1 C7 106.0(5) . . ?
C13 P1 C1 104.0(5) . . ?
C7 P1 C1 107.4(5) . . ?
C13 P1 Au1 113.0(4) . . ?
C7 P1 Au1 111.6(3) . . ?
C1 P1 Au1 114.3(3) . . ?
C19 S1 Au1 101.6(4) . . ?
C19 S2 C20 91.7(7) . . ?

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
C6 C1 C2 C3 -2(2) . . . . ?
P1 C1 C2 C3 -178.7(12) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C2 C1 C6 C5 2.4(19) . . . . ?
P1 C1 C6 C5 178.9(11) . . . . ?
C4 C5 C6 C1 -1(2) . . . . ?
N2 C7 C8 C9 -1(2) . . . . ?
P1 C7 C8 C9 -179.3(10) . . . . ?
C7 C8 C9 C10 -2(2) . . . . ?
C8 C9 C10 C11 3(3) . . . . ?
C9 C10 C11 N2 -3(3) . . . . ?
C8 C7 N2 C11 1(2) . . . . ?
P1 C7 N2 C11 179.5(11) . . . . ?
C10 C11 N2 C7 1(2) . . . . ?
C18 C13 C14 C15 1.6(18) . . . . ?
P1 C13 C14 C15 -175.7(11) . . . . ?
C13 C14 C15 C16 -1(2) . . . . ?
C14 C15 C16 C17 1(2) . . . . ?
C15 C16 C17 C18 -1(2) . . . . ?
C16 C17 C18 C13 1.0(18) . . . . ?
C14 C13 C18 C17 -1.5(17) . . . . ?
P1 C13 C18 C17 175.8(9) . . . . ?
S2 C20 C21 N1 15(3) . . . . ?
S2 C19 N1 C21 -5(2) . . . . ?
S1 C19 N1 C21 177.0(14) . . . . ?
C20 C21 N1 C19 -7(3) . . . . ?
C18 C13 P1 C7 140.8(9) . . . . ?
C14 C13 P1 C7 -41.9(11) . . . . ?
C18 C13 P1 C1 -106.2(9) . . . . ?
C14 C13 P1 C1 71.1(10) . . . . ?
C18 C13 P1 Au1 18.3(10) . . . . ?
C14 C13 P1 Au1 -164.4(8) . . . . ?
C8 C7 P1 C13 -86.6(10) . . . . ?
N2 C7 P1 C13 94.8(12) . . . . ?
C8 C7 P1 C1 162.8(9) . . . . ?
N2 C7 P1 C1 -15.8(12) . . . . ?
C8 C7 P1 Au1 36.7(10) . . . . ?
N2 C7 P1 Au1 -141.9(10) . . . . ?
C2 C1 P1 C13 -46.4(10) . . . . ?
C6 C1 P1 C13 137.0(9) . . . . ?
C2 C1 P1 C7 65.6(10) . . . . ?
C6 C1 P1 C7 -111.0(9) . . . . ?
C2 C1 P1 Au1 -170.0(8) . . . . ?
C6 C1 P1 Au1 13.4(10) . . . . ?
N1 C19 S1 Au1 160.1(14) . . . . ?
S2 C19 S1 Au1 -17.3(8) . . . . ?
N1 C19 S2 C20 12.5(15) . . . . ?
S1 C19 S2 C20 -170.0(10) . . . . ?
C21 C20 S2 C19 -14.6(17) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc1pvx8q
_database_code_depnum_ccdc_archive 'CCDC 1574994'
loop_
_audit_author_name
_audit_author_address
'Reza Halvagar'
;CCERCI
Iran
;
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

_audit_creation_date             2019-07-16T09:54:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Au N3 P S'
_chemical_formula_sum            'C21 H17 Au N3 P S'
_chemical_formula_weight         571.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2477(18)
_cell_length_b                   17.742(3)
_cell_length_c                   12.591(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.63(3)
_cell_angle_gamma                90
_cell_volume                     2061.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9684
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.46

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_diffrn_ambient_temperature      293(2)
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.84
_exptl_crystal_F_000             1096
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 1 -11 0.1
-2 3 7 0.113
0 -6 -1 0.092
1 9 1 0.131
4 -1 3 0.073
0 -3 -4 0.093
-1 5 5 0.106
-5 -1 -6 0.072
-5 2 -2 0.089
-1 -6 2 0.143

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    7.325
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.6704
_exptl_absorpt_correction_T_max  0.7985
_shelx_estimated_absorpt_T_min   0.296
_shelx_estimated_absorpt_T_max   0.474
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_number            14486
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.654
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_number_total             3611
_reflns_number_gt                2437
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows version 2014.1'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3611
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_restrained_S_all      0.871
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.168
_refine_diff_density_min         -1.164
_refine_diff_density_rms         0.11

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.013 8.802 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.102 0.094 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.125 0.123 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.19985(3) 0.41626(2) 0.38218(2) 0.04715(10) Uani 1 d . .
S1 S 0.0760(2) 0.35878(12) 0.51353(17) 0.0581(5) Uani 1 d . .
P1 P 0.3168(2) 0.46449(11) 0.24581(15) 0.0446(5) Uani 1 d . .
N1 N 0.3565(8) 0.3340(4) 0.5705(6) 0.070(2) Uani 1 d . .
N2 N 0.1810(8) 0.2640(4) 0.6581(6) 0.071(2) Uani 1 d . .
N3 N 0.1373(8) 0.4278(5) 0.0743(7) 0.083(2) Uani 1 d . .
C10 C 0.5129(8) 0.4621(4) 0.2708(7) 0.057(2) Uani 1 d . .
C5 C 0.2710(6) 0.4132(4) 0.1241(5) 0.0459(17) Uani 1 d . .
C12 C 0.7457(13) 0.4846(7) 0.2143(15) 0.137(6) Uani 1 d . .
H11 H 0.8062 0.4979 0.1611 0.164 Uiso 1 calc . .
C18 C 0.1498(8) 0.6758(5) 0.2498(7) 0.059(2) Uani 1 d . .
H16 H 0.0895 0.7035 0.2915 0.071 Uiso 1 calc . .
C16 C 0.2722(7) 0.5616(4) 0.2124(6) 0.0447(18) Uani 1 d . .
C14 C 0.7188(14) 0.4446(8) 0.3915(11) 0.112(5) Uani 1 d . .
H9 H 0.7588 0.4306 0.4582 0.135 Uiso 1 calc . .
C9 C 0.3581(9) 0.3561(5) 0.0866(7) 0.071(3) Uani 1 d . .
H4 H 0.4477 0.3452 0.121 0.085 Uiso 1 calc . .
C17 C 0.1821(8) 0.6022(4) 0.2750(6) 0.0486(19) Uani 1 d . .
H17 H 0.1437 0.5798 0.3337 0.058 Uiso 1 calc . .
C7 C 0.1776(11) 0.3313(6) -0.0529(8) 0.082(3) Uani 1 d . .
H6 H 0.1459 0.3049 -0.1138 0.098 Uiso 1 calc . .
C19 C 0.2067(9) 0.7082(5) 0.1631(8) 0.068(2) Uani 1 d . .
H15 H 0.1854 0.7582 0.1458 0.081 Uiso 1 calc . .
C3 C 0.4298(14) 0.2427(7) 0.7030(9) 0.100(4) Uani 1 d . .
H2 H 0.5028 0.2182 0.7438 0.12 Uiso 1 calc . .
C21 C 0.3259(8) 0.5947(4) 0.1247(6) 0.056(2) Uani 1 d . .
H13 H 0.3837 0.567 0.0813 0.067 Uiso 1 calc . .
C11 C 0.6000(10) 0.4823(6) 0.1920(10) 0.104(4) Uani 1 d . .
H12 H 0.5605 0.4943 0.1244 0.125 Uiso 1 calc . .
C4 C 0.2873(14) 0.2288(6) 0.7138(7) 0.086(3) Uani 1 d . .
H1 H 0.2626 0.1927 0.7629 0.103 Uiso 1 calc . .
C8 C 0.3083(11) 0.3158(6) -0.0034(8) 0.083(3) Uani 1 d . .
H5 H 0.3655 0.2778 -0.0297 0.1 Uiso 1 calc . .
C13 C 0.8040(13) 0.4677(7) 0.3126(16) 0.119(6) Uani 1 d . .
H10 H 0.9036 0.4719 0.3268 0.143 Uiso 1 calc . .
C2 C 0.4593(12) 0.2971(7) 0.6254(9) 0.095(3) Uani 1 d . .
H3 H 0.5554 0.3073 0.6126 0.114 Uiso 1 calc . .
C15 C 0.5721(10) 0.4430(6) 0.3680(8) 0.078(3) Uani 1 d . .
H8 H 0.5115 0.4284 0.4204 0.094 Uiso 1 calc . .
C20 C 0.2953(10) 0.6670(5) 0.1015(8) 0.074(3) Uani 1 d . .
H14 H 0.3344 0.6894 0.043 0.089 Uiso 1 calc . .
C1 C 0.2199(9) 0.3155(4) 0.5885(6) 0.054(2) Uani 1 d . .
C6 C 0.0926(10) 0.3858(6) -0.0131(8) 0.081(3) Uani 1 d . .
H7 H 0.0015 0.3948 -0.0462 0.097 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 P1 2.2550(19) . ?
Au1 S1 2.308(2) . ?
S1 C1 1.758(8) . ?
P1 C5 1.809(8) . ?
P1 C16 1.815(7) . ?
P1 C10 1.821(8) . ?
N1 C2 1.314(12) . ?
N1 C1 1.338(10) . ?
N2 C4 1.326(12) . ?
N2 C1 1.331(10) . ?
N3 C6 1.371(11) . ?
N3 C5 1.375(9) . ?
C10 C15 1.351(12) . ?
C10 C11 1.365(12) . ?
C5 C9 1.395(10) . ?
C12 C13 1.351(18) . ?
C12 C11 1.359(15) . ?
C12 H11 0.93 . ?
C18 C19 1.369(11) . ?
C18 C17 1.372(10) . ?
C18 H16 0.93 . ?
C16 C21 1.371(10) . ?
C16 C17 1.384(10) . ?
C14 C13 1.369(18) . ?
C14 C15 1.370(14) . ?
C14 H9 0.93 . ?
C9 C8 1.394(12) . ?
C9 H4 0.93 . ?
C17 H17 0.93 . ?
C7 C8 1.353(12) . ?
C7 C6 1.361(12) . ?
C7 H6 0.93 . ?
C19 C20 1.374(12) . ?
C19 H15 0.93 . ?
C3 C4 1.356(14) . ?
C3 C2 1.413(15) . ?
C3 H2 0.93 . ?
C21 C20 1.341(11) . ?
C21 H13 0.93 . ?
C11 H12 0.93 . ?
C4 H1 0.93 . ?
C8 H5 0.93 . ?
C13 H10 0.93 . ?
C2 H3 0.93 . ?
C15 H8 0.93 . ?
C20 H14 0.93 . ?
C6 H7 0.93 . ?

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
P1 Au1 S1 175.53(8) . . ?
C1 S1 Au1 100.6(3) . . ?
C5 P1 C16 104.1(3) . . ?
C5 P1 C10 108.2(3) . . ?
C16 P1 C10 105.7(3) . . ?
C5 P1 Au1 110.9(2) . . ?
C16 P1 Au1 115.1(2) . . ?
C10 P1 Au1 112.3(3) . . ?
C2 N1 C1 116.6(9) . . ?
C4 N2 C1 116.7(8) . . ?
C6 N3 C5 118.7(8) . . ?
C15 C10 C11 120.0(9) . . ?
C15 C10 P1 120.3(7) . . ?
C11 C10 P1 119.7(7) . . ?
N3 C5 C9 120.3(8) . . ?
N3 C5 P1 116.5(6) . . ?
C9 C5 P1 122.8(6) . . ?
C13 C12 C11 121.0(13) . . ?
C13 C12 H11 119.5 . . ?
C11 C12 H11 119.5 . . ?
C19 C18 C17 119.7(8) . . ?
C19 C18 H16 120.2 . . ?
C17 C18 H16 120.2 . . ?
C21 C16 C17 119.8(7) . . ?
C21 C16 P1 120.3(6) . . ?
C17 C16 P1 119.9(5) . . ?
C13 C14 C15 117.2(12) . . ?
C13 C14 H9 121.4 . . ?
C15 C14 H9 121.4 . . ?
C8 C9 C5 118.7(8) . . ?
C8 C9 H4 120.7 . . ?
C5 C9 H4 120.7 . . ?
C18 C17 C16 119.6(7) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C8 C7 C6 119.6(9) . . ?
C8 C7 H6 120.2 . . ?
C6 C7 H6 120.2 . . ?
C18 C19 C20 120.0(8) . . ?
C18 C19 H15 120 . . ?
C20 C19 H15 120 . . ?
C4 C3 C2 115.1(10) . . ?
C4 C3 H2 122.4 . . ?
C2 C3 H2 122.4 . . ?
C20 C21 C16 120.2(7) . . ?
C20 C21 H13 119.9 . . ?
C16 C21 H13 119.9 . . ?
C12 C11 C10 118.7(11) . . ?
C12 C11 H12 120.6 . . ?
C10 C11 H12 120.6 . . ?
N2 C4 C3 123.7(10) . . ?
N2 C4 H1 118.2 . . ?
C3 C4 H1 118.2 . . ?
C7 C8 C9 120.6(9) . . ?
C7 C8 H5 119.7 . . ?
C9 C8 H5 119.7 . . ?
C12 C13 C14 121.1(12) . . ?
C12 C13 H10 119.5 . . ?
C14 C13 H10 119.5 . . ?
N1 C2 C3 122.6(11) . . ?
N1 C2 H3 118.7 . . ?
C3 C2 H3 118.7 . . ?
C10 C15 C14 121.9(11) . . ?
C10 C15 H8 119 . . ?
C14 C15 H8 119 . . ?
C21 C20 C19 120.7(8) . . ?
C21 C20 H14 119.6 . . ?
C19 C20 H14 119.6 . . ?
N2 C1 N1 125.3(8) . . ?
N2 C1 S1 115.2(7) . . ?
N1 C1 S1 119.5(6) . . ?
C7 C6 N3 122.0(9) . . ?
C7 C6 H7 119 . . ?
N3 C6 H7 119 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 P1 C10 C15 -131.5(7) . . . . ?
C16 P1 C10 C15 117.5(7) . . . . ?
Au1 P1 C10 C15 -8.8(8) . . . . ?
C5 P1 C10 C11 50.8(9) . . . . ?
C16 P1 C10 C11 -60.2(9) . . . . ?
Au1 P1 C10 C11 173.6(8) . . . . ?
C6 N3 C5 C9 -0.7(12) . . . . ?
C6 N3 C5 P1 -174.5(7) . . . . ?
C16 P1 C5 N3 -48.3(6) . . . . ?
C10 P1 C5 N3 -160.4(6) . . . . ?
Au1 P1 C5 N3 76.0(6) . . . . ?
C16 P1 C5 C9 138.1(7) . . . . ?
C10 P1 C5 C9 26.0(8) . . . . ?
Au1 P1 C5 C9 -97.6(6) . . . . ?
C5 P1 C16 C21 -52.3(7) . . . . ?
C10 P1 C16 C21 61.6(7) . . . . ?
Au1 P1 C16 C21 -173.8(5) . . . . ?
C5 P1 C16 C17 126.9(6) . . . . ?
C10 P1 C16 C17 -119.2(6) . . . . ?
Au1 P1 C16 C17 5.4(7) . . . . ?
N3 C5 C9 C8 1.6(13) . . . . ?
P1 C5 C9 C8 174.9(7) . . . . ?
C19 C18 C17 C16 0.1(12) . . . . ?
C21 C16 C17 C18 -1.3(11) . . . . ?
P1 C16 C17 C18 179.5(6) . . . . ?
C17 C18 C19 C20 0.2(13) . . . . ?
C17 C16 C21 C20 2.2(12) . . . . ?
P1 C16 C21 C20 -178.6(7) . . . . ?
C13 C12 C11 C10 0(2) . . . . ?
C15 C10 C11 C12 -1.7(17) . . . . ?
P1 C10 C11 C12 176.0(9) . . . . ?
C1 N2 C4 C3 -0.1(15) . . . . ?
C2 C3 C4 N2 -1.3(17) . . . . ?
C6 C7 C8 C9 -1.4(17) . . . . ?
C5 C9 C8 C7 -0.5(15) . . . . ?
C11 C12 C13 C14 3(2) . . . . ?
C15 C14 C13 C12 -3(2) . . . . ?
C1 N1 C2 C3 -2.6(16) . . . . ?
C4 C3 C2 N1 2.7(18) . . . . ?
C11 C10 C15 C14 1.4(15) . . . . ?
P1 C10 C15 C14 -176.3(8) . . . . ?
C13 C14 C15 C10 1.0(17) . . . . ?
C16 C21 C20 C19 -1.9(14) . . . . ?
C18 C19 C20 C21 0.6(14) . . . . ?
C4 N2 C1 N1 0.3(13) . . . . ?
C4 N2 C1 S1 178.2(7) . . . . ?
C2 N1 C1 N2 1.1(13) . . . . ?
C2 N1 C1 S1 -176.8(7) . . . . ?
Au1 S1 C1 N2 -166.2(6) . . . . ?
Au1 S1 C1 N1 11.9(7) . . . . ?
C8 C7 C6 N3 2.3(17) . . . . ?
C5 N3 C6 C7 -1.2(15) . . . . ?



# END of CIF
